#------------------------------------------------------------------------------ #$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $ #$Revision: 249721 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240201.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240201 loop_ _publ_author_name 'Pettersen, Anna' 'Putra, Okky Dwichandra' 'Light, Mark E.' 'Namatame, Yukiko' _publ_section_title ; Invitation to Submit: The Cambridge Structural Database " A peculiar dehydration and solid-solid phase transition of the active pharmaceutical ingredient AZD9898 based on in situ single crystal-to-single crystal transformations " ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00276C _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H19 Cl F3 N3 O4' _chemical_formula_sum 'C20 H19 Cl F3 N3 O4' _chemical_formula_weight 457.83 _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2016-02-10 _audit_creation_method ; Olex2 1.2-alpha (compiled 2016.01.25 svn.r3250 for OlexSys, GUI svn.r5148) ; _audit_update_record ; 2020-02-07 deposited with the CCDC. 2020-03-24 downloaded from the CCDC. ; _cell_angle_alpha 103.187(4) _cell_angle_beta 105.203(4) _cell_angle_gamma 104.668(4) _cell_formula_units_Z 2 _cell_length_a 9.1429(4) _cell_length_b 11.0950(5) _cell_length_c 11.6725(5) _cell_measurement_reflns_used 8769 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 29.8300 _cell_measurement_theta_min 2.1120 _cell_volume 1048.93(9) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 300(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 28.5714 _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -58.00 71.00 1.00 10.00 -- -19.00 72.00 -30.00 129 2 \w -58.00 71.00 1.00 10.00 -- -19.00 72.00 150.00 129 3 \w -80.00 20.00 1.00 10.00 -- -19.00 -72.00-150.00 100 4 \w -69.00 20.00 1.00 10.00 -- -19.00 -72.00 30.00 89 5 \w -58.00 71.00 1.00 10.00 -- -19.00 72.00-120.00 129 6 \w -100.00 -14.00 1.00 10.00 -- -19.00 0.00-150.00 86 7 \w -58.00 5.00 1.00 10.00 -- -19.00 72.00 60.00 63 8 \w -15.00 10.00 1.00 10.00 -- -19.00 -54.00 60.00 25 9 \w -16.00 11.00 1.00 10.00 -- -19.00 -54.00-120.00 27 10 \w -35.00 -14.00 1.00 10.00 -- -19.00 0.00 30.00 21 11 \w -58.00 -37.00 1.00 10.00 -- -19.00 72.00 -90.00 21 12 \w -58.00 -37.00 1.00 10.00 -- -19.00 72.00 0.00 21 ; _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 FRE-VHF' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0051985000 _diffrn_orient_matrix_UB_12 -0.0222133000 _diffrn_orient_matrix_UB_13 -0.0603240000 _diffrn_orient_matrix_UB_21 0.0698630000 _diffrn_orient_matrix_UB_22 -0.0147800000 _diffrn_orient_matrix_UB_23 0.0264933000 _diffrn_orient_matrix_UB_31 -0.0486026000 _diffrn_orient_matrix_UB_32 -0.0643261000 _diffrn_orient_matrix_UB_33 -0.0079223000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator 'Confocal mirrors, VHF Varimax' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_unetI/netI 0.0465 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 21557 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 28.700 _diffrn_reflns_theta_min 3.098 _diffrn_source 'Rotating Anode' _diffrn_source_current 55.0 _diffrn_source_power 2.475 _diffrn_source_target Mo _diffrn_source_type 'Rotating Anode' _diffrn_source_voltage 45.0 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.450 _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_recrystallization_method 'The material was recrystallised from --- by slow evaporation' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.289 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details ; Flack x determined using 2597 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.03(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 571 _refine_ls_number_reflns 10677 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0515 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.1249P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1096 _refine_ls_wR_factor_ref 0.1252 _reflns_Friedel_coverage 0.979 _reflns_Friedel_fraction_full 0.980 _reflns_Friedel_fraction_max 0.976 _reflns_number_gt 7342 _reflns_number_total 10677 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00276c2.cif _cod_data_source_block 2016scas0001_r_300k _cod_original_cell_volume 1048.93(8) _cod_database_code 7240201 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _diffrn_measurement_device_type2 'Rigaku AFC12 (Right)' _reflns_odcompleteness_completeness 90.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.83 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, {H20A,H20B} of C207, {H11G,H11H} of C119, {H21G,H21H} of C219, {H10A,H10B} of C107 At 1.5 times of: All C(H,H,H) groups, {H203,H103} of C220 2. Restrained distances O103-H103 0.84 with sigma of 0.02 O203-H203 0.84 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C117(H117), C118(H118), C217(H217), C218(H218) 3.b Secondary CH2 refined with riding coordinates: C107(H10A,H10B), C119(H11G,H11H), C207(H20A,H20B), C219(H21G,H21H) 3.c Aromatic/amide H refined with riding coordinates: C101(H101), C104(H104), C114(H114), C201(H201), C204(H204), C214(H214) 3.d Idealised Me refined as rotating group: C109(H10C,H10D,H10E), C110(H11A,H11B,H11C), C115(H11D,H11E,H11F), C209(H20C, H20D,H20E), C210(H21A,H21B,H21C), C215(H21D,H21E,H21F) ; _shelx_res_file ; 2016scas0001_r_300k.res created by SHELXL-2014/7 TITL 2016scas0001_R_100K in P1 #1 REM reset to P1 #1 CELL 0.71073 9.142883 11.095039 11.672504 103.1873 105.2031 104.6678 ZERR 2 0.000378 0.000467 0.000534 0.0038 0.0038 0.0036 LATT -1 SFAC C H Cl F N O UNIT 40 38 2 6 6 8 EQIV $1 1+X,+Y,1+Z EQIV $2 -1+X,+Y,-1+Z DFIX 0.84 O103 H103 DFIX 0.84 O203 H203 L.S. 4 0 0 PLAN 50 TEMP 27(2) HTAB O103 N203_$1 HTAB O203 N103_$2 BOND MORE -1 BOND $H CONF fmap 2 53 acta 52 SHEL 7 0.74 OMIT -1 -2 3 OMIT 0 1 2 OMIT 2 -2 -2 OMIT 1 2 -3 OMIT 3 4 -3 OMIT 0 -1 -2 OMIT 0 -2 -1 OMIT 1 5 -4 OMIT 1 3 -3 OMIT -2 2 2 OMIT 0 0 -2 REM REM REM WGHT 0.053000 0.124900 FVAR 0.80902 CL11 3 0.411192 -0.396962 -0.020499 11.00000 0.09679 0.04041 = 0.06351 0.00862 0.01189 0.02754 F101 4 0.135380 -0.373957 0.048330 11.00000 0.08300 0.04700 = 0.07309 0.02191 0.02402 -0.00788 F102 4 0.262707 0.077319 0.130518 11.00000 0.05810 0.05353 = 0.07388 0.01457 0.03498 0.02492 F103 4 0.245251 0.028333 -0.139281 11.00000 0.04262 0.07032 = 0.07369 0.03703 0.00505 0.00618 O101 6 0.828200 0.530970 0.259386 11.00000 0.05117 0.03510 = 0.04081 0.01271 0.01362 0.00077 O102 6 0.847917 0.617744 0.507300 11.00000 0.12649 0.03998 = 0.05055 0.01068 0.01548 0.02708 O103 6 0.955451 0.362289 0.813268 11.00000 0.06129 0.06211 = 0.04796 0.02349 0.01546 0.01959 O104 6 0.732069 0.387168 0.840670 11.00000 0.08295 0.10620 = 0.06926 0.03546 0.04535 0.03568 N101 5 0.528593 0.097403 0.059721 11.00000 0.03785 0.03068 = 0.03295 0.00932 0.00949 0.00937 N102 5 0.683518 0.314855 0.160684 11.00000 0.03290 0.03083 = 0.03559 0.00996 0.01103 0.00890 N103 5 0.709003 0.278765 0.388737 11.00000 0.04162 0.03754 = 0.03579 0.01416 0.01044 0.01274 C101 1 0.469132 -0.137144 0.026473 11.00000 0.03798 0.03374 = 0.03720 0.00954 0.00819 0.00866 AFIX 43 H101 2 0.560837 -0.133552 0.005032 11.00000 -1.20000 AFIX 0 C102 1 0.368823 -0.255697 0.022449 11.00000 0.05821 0.03296 = 0.03054 0.00576 0.00271 0.01365 C103 1 0.233315 -0.258491 0.053629 11.00000 0.05210 0.03992 = 0.04238 0.01493 0.00974 -0.00484 C104 1 0.195174 -0.147289 0.090017 11.00000 0.04690 0.05229 = 0.04681 0.01340 0.01985 0.00808 AFIX 43 H104 2 0.103350 -0.150348 0.111156 11.00000 -1.20000 AFIX 0 C105 1 0.297679 -0.031985 0.093884 11.00000 0.04522 0.03820 = 0.04030 0.01033 0.01664 0.01350 C106 1 0.432738 -0.024603 0.062302 11.00000 0.03642 0.03322 = 0.03392 0.00885 0.00661 0.00808 C107 1 0.526801 0.108961 -0.061892 11.00000 0.04308 0.04243 = 0.03443 0.00795 0.01502 0.01367 AFIX 23 H10A 2 0.537063 0.029902 -0.110306 11.00000 -1.20000 H10B 2 0.620141 0.181987 -0.050078 11.00000 -1.20000 AFIX 0 C108 1 0.377579 0.129653 -0.137253 11.00000 0.04435 0.04609 = 0.03857 0.01936 0.01107 0.01277 C109 1 0.371129 0.106861 -0.270460 11.00000 0.08219 0.07351 = 0.04408 0.02243 0.01280 0.03205 AFIX 137 H10C 2 0.371482 0.019654 -0.304669 11.00000 -1.50000 H10D 2 0.463041 0.169539 -0.273460 11.00000 -1.50000 H10E 2 0.274736 0.116802 -0.318504 11.00000 -1.50000 AFIX 0 C110 1 0.360353 0.257504 -0.078995 11.00000 0.05947 0.06238 = 0.05637 0.02333 0.01744 0.03256 AFIX 137 H11A 2 0.264122 0.264756 -0.130401 11.00000 -1.50000 H11B 2 0.451653 0.328326 -0.071712 11.00000 -1.50000 H11C 2 0.354206 0.261648 0.002592 11.00000 -1.50000 AFIX 0 C111 1 0.613811 0.197721 0.168423 11.00000 0.03482 0.03260 = 0.03373 0.00852 0.00802 0.01123 C112 1 0.758940 0.412724 0.264941 11.00000 0.03064 0.03478 = 0.04056 0.01096 0.01001 0.00837 C113 1 0.772161 0.398687 0.383153 11.00000 0.03370 0.03865 = 0.03617 0.01116 0.00864 0.00950 C114 1 0.629435 0.179315 0.284856 11.00000 0.04380 0.03577 = 0.03825 0.01430 0.01129 0.00828 AFIX 43 H114 2 0.583354 0.096255 0.289162 11.00000 -1.20000 AFIX 0 C115 1 0.814145 0.544968 0.138441 11.00000 0.06829 0.05207 = 0.04719 0.02358 0.02060 0.01128 AFIX 137 H11D 2 0.703799 0.530505 0.093345 11.00000 -1.50000 H11E 2 0.850472 0.481850 0.093110 11.00000 -1.50000 H11F 2 0.878735 0.631939 0.147747 11.00000 -1.50000 AFIX 0 C116 1 0.844062 0.506669 0.502584 11.00000 0.05255 0.04326 = 0.04289 0.01119 0.01606 0.01145 C117 1 0.911920 0.473502 0.616430 11.00000 0.04586 0.04259 = 0.03378 0.00780 0.00909 0.00541 AFIX 13 H117 2 0.946400 0.396187 0.604022 11.00000 -1.20000 AFIX 0 C118 1 0.848030 0.501750 0.722669 11.00000 0.06528 0.05925 = 0.04204 0.01043 0.02102 0.02285 AFIX 13 H118 2 0.763590 0.541880 0.709978 11.00000 -1.20000 AFIX 0 C119 1 1.009787 0.584169 0.732051 11.00000 0.07432 0.05196 = 0.03840 0.00394 0.00386 -0.00184 AFIX 23 H11G 2 1.022644 0.672406 0.727907 11.00000 -1.20000 H11H 2 1.103017 0.574958 0.787502 11.00000 -1.20000 AFIX 0 C120 1 0.836961 0.411062 0.797667 11.00000 0.06245 0.06477 = 0.03591 0.00586 0.01751 0.01514 CL12 3 0.298189 0.910630 0.413553 11.00000 0.09889 0.04072 = 0.07130 0.00820 0.02137 0.02839 F201 4 0.577830 0.886626 0.350730 11.00000 0.08139 0.04860 = 0.06989 0.01645 0.02492 -0.00687 F202 4 0.442342 0.434599 0.261248 11.00000 0.05770 0.05543 = 0.08408 0.02073 0.03585 0.02976 F203 4 0.450638 0.488391 0.535513 11.00000 0.05051 0.09431 = 0.07300 0.04248 0.00311 0.00910 O201 6 -0.130250 -0.018475 0.130041 11.00000 0.05152 0.04160 = 0.05258 0.01802 0.01444 0.00611 O202 6 -0.263357 -0.093569 -0.124620 11.00000 0.06314 0.04566 = 0.05142 0.00679 0.01451 0.00305 N201 5 0.172467 0.414883 0.325057 11.00000 0.04364 0.03969 = 0.03386 0.01360 0.01393 0.01193 N202 5 0.016195 0.197771 0.226065 11.00000 0.03754 0.04263 = 0.03798 0.01807 0.01452 0.01567 N203 5 -0.004593 0.230786 -0.002581 11.00000 0.04156 0.04200 = 0.03722 0.01432 0.01053 0.01207 C201 1 0.235889 0.650286 0.360618 11.00000 0.04211 0.04705 = 0.03309 0.00931 0.00747 0.01842 AFIX 43 H201 2 0.142177 0.647550 0.378771 11.00000 -1.20000 AFIX 0 C202 1 0.340039 0.767996 0.369172 11.00000 0.05690 0.03302 = 0.03773 0.00942 0.00843 0.01440 C203 1 0.476319 0.771246 0.342728 11.00000 0.05461 0.04148 = 0.03664 0.00829 0.01006 0.00111 C204 1 0.515073 0.662006 0.306743 11.00000 0.04222 0.06025 = 0.05160 0.01772 0.01918 0.00607 AFIX 43 H204 2 0.609487 0.666118 0.289325 11.00000 -1.20000 AFIX 0 C205 1 0.408637 0.545035 0.297180 11.00000 0.04288 0.04366 = 0.04634 0.01218 0.01522 0.01749 C206 1 0.269897 0.535919 0.325127 11.00000 0.03682 0.03666 = 0.03177 0.01213 0.00858 0.01133 C207 1 0.170523 0.403621 0.447352 11.00000 0.04733 0.03985 = 0.03346 0.01378 0.01667 0.01568 AFIX 23 H20A 2 0.077467 0.329756 0.434342 11.00000 -1.20000 H20B 2 0.157389 0.482138 0.494029 11.00000 -1.20000 AFIX 0 C208 1 0.317357 0.385576 0.525334 11.00000 0.05167 0.05386 = 0.04138 0.01911 0.01306 0.01787 C209 1 0.312472 0.398993 0.654798 11.00000 0.09320 0.08782 = 0.04035 0.02565 0.02101 0.04084 AFIX 137 H20C 2 0.408912 0.391660 0.705799 11.00000 -1.50000 H20D 2 0.220919 0.330832 0.651294 11.00000 -1.50000 H20E 2 0.304455 0.483085 0.690270 11.00000 -1.50000 AFIX 0 C210 1 0.343302 0.260567 0.467898 11.00000 0.07921 0.08666 = 0.06145 0.02869 0.02271 0.05719 AFIX 137 H21A 2 0.349969 0.257826 0.386674 11.00000 -1.50000 H21B 2 0.255019 0.186812 0.459987 11.00000 -1.50000 H21C 2 0.441502 0.257150 0.520315 11.00000 -1.50000 AFIX 0 C211 1 0.088740 0.313502 0.217495 11.00000 0.03109 0.03853 = 0.03674 0.01615 0.01320 0.01472 C212 1 -0.062761 0.099218 0.121675 11.00000 0.03031 0.03577 = 0.04264 0.01651 0.01201 0.01038 C213 1 -0.074271 0.111801 0.003768 11.00000 0.03413 0.03792 = 0.04107 0.01202 0.00966 0.01308 C214 1 0.075512 0.329087 0.099975 11.00000 0.04570 0.03452 = 0.03933 0.01288 0.01014 0.01067 AFIX 43 H214 2 0.124785 0.411096 0.094952 11.00000 -1.20000 AFIX 0 C215 1 -0.108015 -0.028890 0.252969 11.00000 0.07019 0.05261 = 0.06644 0.03426 0.03263 0.01629 AFIX 137 H21D 2 -0.164559 -0.117022 0.246899 11.00000 -1.50000 H21E 2 -0.149043 0.030876 0.297503 11.00000 -1.50000 H21F 2 0.004473 -0.007510 0.296966 11.00000 -1.50000 AFIX 0 C216 1 -0.158588 0.002997 -0.115874 11.00000 0.03734 0.03847 = 0.04333 0.00987 0.00731 0.01321 PART 1 O203 6 -0.316603 0.155338 -0.436627 11.00000 0.04958 0.05322 = 0.04614 0.02156 0.01182 0.01477 O204 6 -0.087601 0.122592 -0.438368 11.00000 0.05960 0.08072 = 0.06871 0.02621 0.03043 0.02663 C217 1 -0.112632 0.021456 -0.223794 11.00000 0.04213 0.05139 = 0.03879 0.00824 0.00815 0.01808 AFIX 13 H217 2 -0.007474 0.086433 -0.205421 11.00000 -1.20000 AFIX 0 C218 1 -0.245691 0.008468 -0.340000 11.00000 0.04552 0.04151 = 0.04234 0.01028 0.00675 0.00613 AFIX 13 H218 2 -0.354846 -0.013799 -0.336430 11.00000 -1.20000 AFIX 0 C219 1 -0.169562 -0.094205 -0.338434 11.00000 0.10123 0.05115 = 0.04778 0.00861 0.02697 0.03354 AFIX 23 H21G 2 -0.098787 -0.100040 -0.386985 11.00000 -1.20000 H21H 2 -0.232258 -0.177813 -0.336029 11.00000 -1.20000 AFIX 0 C220 1 -0.205459 0.099725 -0.409883 11.00000 0.05060 0.04140 = 0.03275 0.00502 0.00719 0.00665 PART 0 H203 2 -0.296790 0.210065 -0.476791 11.00000 -1.50000 H103 2 0.962139 0.320348 0.866696 11.00000 -1.50000 HKLF 4 REM 2016scas0001_R_100K in P1 #1 REM R1 = 0.0515 for 7342 Fo > 4sig(Fo) and 0.0839 for all 10677 data REM 571 parameters refined using 5 restraints END WGHT 0.0530 0.1249 REM Highest difference peak 0.289, deepest hole -0.284, 1-sigma level 0.039 Q1 1 0.1892 0.8769 0.4025 11.00000 0.05 0.29 Q2 1 0.5196 -0.3630 -0.0200 11.00000 0.05 0.28 Q3 1 0.0780 0.3310 0.1634 11.00000 0.05 0.21 Q4 1 0.6173 0.1814 0.2211 11.00000 0.05 0.19 Q5 1 -0.0122 0.1459 0.1765 11.00000 0.05 0.18 Q6 1 0.0392 0.1693 0.2852 11.00000 0.05 0.17 Q7 1 0.7835 0.7074 -0.0378 11.00000 0.05 0.17 Q8 1 0.5612 0.1411 0.1021 11.00000 0.05 0.17 Q9 1 0.1341 0.3739 0.2850 11.00000 0.05 0.16 Q10 1 0.6443 0.3441 0.1012 11.00000 0.05 0.16 Q11 1 0.4823 0.0391 0.0656 11.00000 0.05 0.16 Q12 1 0.8108 0.4453 0.4375 11.00000 0.05 0.15 Q13 1 -0.1150 0.0599 -0.0591 11.00000 0.05 0.15 Q14 1 0.6806 0.2995 -0.0222 11.00000 0.05 0.15 Q15 1 0.7521 0.4037 0.3280 11.00000 0.05 0.15 Q16 1 0.3474 0.1812 -0.1196 11.00000 0.05 0.15 Q17 1 0.7270 0.2645 0.4507 11.00000 0.05 0.15 Q18 1 0.6005 0.9126 0.3398 11.00000 0.05 0.14 Q19 1 0.2456 -0.1871 -0.3578 11.00000 0.05 0.14 Q20 1 0.5183 0.0499 -0.1016 11.00000 0.05 0.14 Q21 1 0.1709 0.4125 0.3791 11.00000 0.05 0.14 Q22 1 1.2002 0.6822 0.6751 11.00000 0.05 0.14 Q23 1 -0.0811 -0.1913 0.4125 11.00000 0.05 0.14 Q24 1 0.0629 -0.1217 0.0904 11.00000 0.05 0.14 Q25 1 0.1462 -0.0384 -0.1747 11.00000 0.05 0.14 Q26 1 1.3063 0.7611 0.7173 11.00000 0.05 0.14 Q27 1 0.0031 0.1132 0.1004 11.00000 0.05 0.13 Q28 1 0.0068 0.2825 0.0433 11.00000 0.05 0.13 Q29 1 0.6852 0.2286 0.3334 11.00000 0.05 0.13 Q30 1 0.7146 0.3603 0.2098 11.00000 0.05 0.13 Q31 1 0.7393 0.4755 0.8821 11.00000 0.05 0.13 Q32 1 0.3836 0.2245 0.2423 11.00000 0.05 0.13 Q33 1 -0.3156 -0.2178 -0.2929 11.00000 0.05 0.13 Q34 1 -0.0186 0.0443 -0.4894 11.00000 0.05 0.13 Q35 1 -0.2098 0.3022 -0.4951 11.00000 0.05 0.13 Q36 1 0.5354 0.1005 0.0201 11.00000 0.05 0.13 Q37 1 0.4288 -0.0794 0.0130 11.00000 0.05 0.13 Q38 1 -0.0199 0.2524 -0.0638 11.00000 0.05 0.13 Q39 1 0.4056 0.3233 0.0106 11.00000 0.05 0.13 Q40 1 0.0632 0.1522 0.4818 11.00000 0.05 0.13 Q41 1 0.3629 0.5601 0.3370 11.00000 0.05 0.13 Q42 1 0.5769 0.0615 0.0666 11.00000 0.05 0.13 Q43 1 0.4555 0.2524 0.3422 11.00000 0.05 0.13 Q44 1 0.7114 0.4786 0.6069 11.00000 0.05 0.13 Q45 1 0.0515 0.2816 0.0602 11.00000 0.05 0.13 Q46 1 0.4391 -0.1232 -0.3577 11.00000 0.05 0.13 Q47 1 0.9549 0.4652 0.9644 11.00000 0.05 0.12 Q48 1 0.7263 0.5328 0.6744 11.00000 0.05 0.12 Q49 1 0.0977 -0.3993 0.0468 11.00000 0.05 0.12 Q50 1 0.4407 -0.0537 0.2590 11.00000 0.05 0.12 ; _shelx_res_checksum 61067 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2016-02-09 _olex2_date_sample_submission 2016-01-26 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder with superglue' _olex2_submission_original_sample_id 'Az13762986 Type 11, E15-013371-F' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.042 _oxdiff_exptl_absorpt_empirical_full_min 0.552 loop_ _space_group_symop_operation_xyz 'x, y, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl11 Cl 0.41119(17) -0.39696(13) -0.02050(14) 0.0706(4) Uani 1 1 d . . . . . F101 F 0.1354(4) -0.3740(3) 0.0483(3) 0.0737(10) Uani 1 1 d . . . . . F102 F 0.2627(3) 0.0773(3) 0.1305(3) 0.0589(8) Uani 1 1 d . . . . . F103 F 0.2453(3) 0.0283(3) -0.1393(3) 0.0653(9) Uani 1 1 d . . . . . O101 O 0.8282(3) 0.5310(3) 0.2594(3) 0.0454(8) Uani 1 1 d . . . . . O102 O 0.8479(5) 0.6177(3) 0.5073(3) 0.0762(11) Uani 1 1 d . . . . . O103 O 0.9555(4) 0.3623(4) 0.8133(3) 0.0569(9) Uani 1 1 d D . . . . O104 O 0.7321(5) 0.3872(5) 0.8407(4) 0.0798(12) Uani 1 1 d . . . . . N101 N 0.5286(4) 0.0974(3) 0.0597(3) 0.0349(8) Uani 1 1 d . . . . . N102 N 0.6835(4) 0.3149(3) 0.1607(3) 0.0337(8) Uani 1 1 d . . . . . N103 N 0.7090(4) 0.2788(4) 0.3887(3) 0.0385(9) Uani 1 1 d . . . . . C101 C 0.4691(5) -0.1371(4) 0.0265(4) 0.0382(10) Uani 1 1 d . . . . . H101 H 0.5608 -0.1336 0.0050 0.046 Uiso 1 1 calc R . . . . C102 C 0.3688(6) -0.2557(5) 0.0224(4) 0.0442(12) Uani 1 1 d . . . . . C103 C 0.2333(5) -0.2585(5) 0.0536(5) 0.0498(13) Uani 1 1 d . . . . . C104 C 0.1952(5) -0.1473(5) 0.0900(5) 0.0500(13) Uani 1 1 d . . . . . H104 H 0.1033 -0.1503 0.1112 0.060 Uiso 1 1 calc R . . . . C105 C 0.2977(5) -0.0320(5) 0.0939(4) 0.0412(11) Uani 1 1 d . . . . . C106 C 0.4327(5) -0.0246(4) 0.0623(4) 0.0367(10) Uani 1 1 d . . . . . C107 C 0.5268(5) 0.1090(5) -0.0619(4) 0.0405(11) Uani 1 1 d . . . . . H10A H 0.5371 0.0299 -0.1103 0.049 Uiso 1 1 calc R . . . . H10B H 0.6201 0.1820 -0.0501 0.049 Uiso 1 1 calc R . . . . C108 C 0.3776(5) 0.1297(5) -0.1373(4) 0.0430(11) Uani 1 1 d . . . . . C109 C 0.3711(7) 0.1069(7) -0.2705(5) 0.0665(16) Uani 1 1 d . . . . . H10C H 0.3715 0.0197 -0.3047 0.100 Uiso 1 1 calc GR . . . . H10D H 0.4630 0.1695 -0.2735 0.100 Uiso 1 1 calc GR . . . . H10E H 0.2747 0.1168 -0.3185 0.100 Uiso 1 1 calc GR . . . . C110 C 0.3604(6) 0.2575(6) -0.0790(5) 0.0566(14) Uani 1 1 d . . . . . H11A H 0.2641 0.2648 -0.1304 0.085 Uiso 1 1 calc GR . . . . H11B H 0.4517 0.3283 -0.0717 0.085 Uiso 1 1 calc GR . . . . H11C H 0.3542 0.2616 0.0026 0.085 Uiso 1 1 calc GR . . . . C111 C 0.6138(4) 0.1977(4) 0.1684(4) 0.0348(10) Uani 1 1 d . . . . . C112 C 0.7589(5) 0.4127(4) 0.2649(4) 0.0364(10) Uani 1 1 d . . . . . C113 C 0.7722(5) 0.3987(4) 0.3832(4) 0.0375(10) Uani 1 1 d . . . . . C114 C 0.6294(5) 0.1793(5) 0.2849(4) 0.0404(11) Uani 1 1 d . . . . . H114 H 0.5834 0.0963 0.2892 0.048 Uiso 1 1 calc R . . . . C115 C 0.8141(6) 0.5450(5) 0.1384(5) 0.0560(14) Uani 1 1 d . . . . . H11D H 0.7038 0.5305 0.0933 0.084 Uiso 1 1 calc GR . . . . H11E H 0.8505 0.4819 0.0931 0.084 Uiso 1 1 calc GR . . . . H11F H 0.8787 0.6319 0.1477 0.084 Uiso 1 1 calc GR . . . . C116 C 0.8441(6) 0.5067(5) 0.5026(5) 0.0476(12) Uani 1 1 d . . . . . C117 C 0.9119(5) 0.4735(4) 0.6164(4) 0.0443(9) Uani 1 1 d . . . . . H117 H 0.9464 0.3962 0.6040 0.053 Uiso 1 1 calc R . . . . C118 C 0.8480(6) 0.5017(5) 0.7227(4) 0.0555(11) Uani 1 1 d . . . . . H118 H 0.7636 0.5419 0.7100 0.067 Uiso 1 1 calc R . . . . C119 C 1.0098(6) 0.5842(5) 0.7321(4) 0.0646(13) Uani 1 1 d . . . . . H11G H 1.0226 0.6724 0.7279 0.078 Uiso 1 1 calc R . . . . H11H H 1.1030 0.5750 0.7875 0.078 Uiso 1 1 calc R . . . . C120 C 0.8370(6) 0.4111(6) 0.7977(5) 0.0572(13) Uani 1 1 d . . . . . Cl12 Cl 0.29819(18) 0.91063(13) 0.41355(15) 0.0726(4) Uani 1 1 d . . . . . F201 F 0.5778(4) 0.8866(3) 0.3507(3) 0.0730(10) Uani 1 1 d . . . . . F202 F 0.4423(3) 0.4346(3) 0.2612(3) 0.0613(8) Uani 1 1 d . . . . . F203 F 0.4506(4) 0.4884(4) 0.5355(3) 0.0765(10) Uani 1 1 d . . . . . O201 O -0.1303(4) -0.0185(3) 0.1300(3) 0.0506(9) Uani 1 1 d . . . . . O202 O -0.2634(4) -0.0936(3) -0.1246(3) 0.0590(8) Uani 1 1 d . . . . . N201 N 0.1725(4) 0.4149(4) 0.3251(4) 0.0389(9) Uani 1 1 d . . . . . N202 N 0.0162(4) 0.1978(4) 0.2261(3) 0.0376(9) Uani 1 1 d . . . . . N203 N -0.0046(4) 0.2308(4) -0.0026(4) 0.0409(9) Uani 1 1 d . . . . . C201 C 0.2359(5) 0.6503(5) 0.3606(4) 0.0417(11) Uani 1 1 d . . . . . H201 H 0.1422 0.6476 0.3788 0.050 Uiso 1 1 calc R . . . . C202 C 0.3400(6) 0.7680(5) 0.3692(4) 0.0446(12) Uani 1 1 d . . . . . C203 C 0.4763(6) 0.7712(5) 0.3427(5) 0.0491(13) Uani 1 1 d . . . . . C204 C 0.5151(6) 0.6620(6) 0.3067(5) 0.0529(13) Uani 1 1 d . . . . . H204 H 0.6095 0.6661 0.2893 0.063 Uiso 1 1 calc R . . . . C205 C 0.4086(5) 0.5450(5) 0.2972(5) 0.0440(12) Uani 1 1 d . . . . . C206 C 0.2699(5) 0.5359(4) 0.3251(4) 0.0357(10) Uani 1 1 d . . . . . C207 C 0.1705(5) 0.4036(5) 0.4474(4) 0.0390(10) Uani 1 1 d . . . . . H20A H 0.0775 0.3298 0.4343 0.047 Uiso 1 1 calc R . . . . H20B H 0.1574 0.4821 0.4940 0.047 Uiso 1 1 calc R . . . . C208 C 0.3174(6) 0.3856(5) 0.5253(5) 0.0487(12) Uani 1 1 d . . . . . C209 C 0.3125(8) 0.3990(7) 0.6548(6) 0.0710(17) Uani 1 1 d . . . . . H20C H 0.4089 0.3917 0.7058 0.107 Uiso 1 1 calc GR . . . . H20D H 0.2209 0.3308 0.6513 0.107 Uiso 1 1 calc GR . . . . H20E H 0.3045 0.4831 0.6903 0.107 Uiso 1 1 calc GR . . . . C210 C 0.3433(8) 0.2606(7) 0.4679(6) 0.0691(17) Uani 1 1 d . . . . . H21A H 0.3500 0.2578 0.3867 0.104 Uiso 1 1 calc GR . . . . H21B H 0.2550 0.1868 0.4600 0.104 Uiso 1 1 calc GR . . . . H21C H 0.4415 0.2572 0.5203 0.104 Uiso 1 1 calc GR . . . . C211 C 0.0887(4) 0.3135(4) 0.2175(4) 0.0337(9) Uani 1 1 d . . . . . C212 C -0.0628(5) 0.0992(5) 0.1217(4) 0.0357(10) Uani 1 1 d . . . . . C213 C -0.0743(5) 0.1118(5) 0.0038(4) 0.0382(10) Uani 1 1 d . . . . . C214 C 0.0755(5) 0.3291(5) 0.1000(4) 0.0411(11) Uani 1 1 d . . . . . H214 H 0.1248 0.4111 0.0950 0.049 Uiso 1 1 calc R . . . . C215 C -0.1080(6) -0.0289(6) 0.2530(6) 0.0591(15) Uani 1 1 d . . . . . H21D H -0.1646 -0.1170 0.2469 0.089 Uiso 1 1 calc GR . . . . H21E H -0.1490 0.0309 0.2975 0.089 Uiso 1 1 calc GR . . . . H21F H 0.0045 -0.0075 0.2970 0.089 Uiso 1 1 calc GR . . . . C216 C -0.1586(5) 0.0030(5) -0.1159(5) 0.0415(11) Uani 1 1 d . . . . . O203 O -0.3166(4) 0.1553(3) -0.4366(3) 0.0500(8) Uani 1 1 d D . . A 1 O204 O -0.0876(4) 0.1226(4) -0.4384(4) 0.0667(10) Uani 1 1 d . . . A 1 C217 C -0.1126(5) 0.0215(4) -0.2238(4) 0.0459(10) Uani 1 1 d . . . A 1 H217 H -0.0075 0.0864 -0.2054 0.055 Uiso 1 1 calc R . . A 1 C218 C -0.2457(5) 0.0085(4) -0.3400(4) 0.0471(10) Uani 1 1 d . . . A 1 H218 H -0.3548 -0.0138 -0.3364 0.056 Uiso 1 1 calc R . . A 1 C219 C -0.1696(7) -0.0942(5) -0.3384(5) 0.0660(13) Uani 1 1 d . . . A 1 H21G H -0.0988 -0.1000 -0.3870 0.079 Uiso 1 1 calc R . . A 1 H21H H -0.2323 -0.1778 -0.3360 0.079 Uiso 1 1 calc R . . A 1 C220 C -0.2055(5) 0.0997(4) -0.4099(4) 0.0460(11) Uani 1 1 d . . . A 1 H203 H -0.297(6) 0.210(5) -0.477(5) 0.069 Uiso 1 1 d DR . . . . H103 H 0.962(6) 0.320(5) 0.867(5) 0.069 Uiso 1 1 d DR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0968(10) 0.0404(8) 0.0635(10) 0.0086(7) 0.0119(7) 0.0275(7) F101 0.083(2) 0.0470(19) 0.073(2) 0.0219(17) 0.0240(17) -0.0079(15) F102 0.0581(17) 0.054(2) 0.074(2) 0.0146(17) 0.0350(15) 0.0249(15) F103 0.0426(14) 0.070(2) 0.074(2) 0.0370(18) 0.0051(13) 0.0062(13) O101 0.0512(18) 0.0351(18) 0.041(2) 0.0127(16) 0.0136(14) 0.0008(14) O102 0.126(3) 0.0400(17) 0.051(2) 0.0107(15) 0.015(2) 0.0271(19) O103 0.061(2) 0.062(2) 0.048(2) 0.0235(17) 0.0155(15) 0.0196(17) O104 0.083(3) 0.106(3) 0.069(3) 0.035(2) 0.045(2) 0.036(2) N101 0.0379(18) 0.031(2) 0.033(2) 0.0093(17) 0.0095(14) 0.0094(15) N102 0.0329(17) 0.031(2) 0.036(2) 0.0100(17) 0.0110(14) 0.0089(14) N103 0.0416(19) 0.038(2) 0.036(2) 0.0142(19) 0.0104(15) 0.0127(16) C101 0.038(2) 0.034(2) 0.037(3) 0.010(2) 0.0082(17) 0.0087(18) C102 0.058(3) 0.033(3) 0.031(3) 0.006(2) 0.0027(19) 0.014(2) C103 0.052(3) 0.040(3) 0.042(3) 0.015(2) 0.010(2) -0.005(2) C104 0.047(3) 0.052(3) 0.047(3) 0.013(3) 0.020(2) 0.008(2) C105 0.045(2) 0.038(3) 0.040(3) 0.010(2) 0.017(2) 0.014(2) C106 0.036(2) 0.033(3) 0.034(3) 0.009(2) 0.0066(17) 0.0081(18) C107 0.043(2) 0.042(3) 0.034(3) 0.008(2) 0.0150(18) 0.014(2) C108 0.044(2) 0.046(3) 0.039(3) 0.019(2) 0.0111(19) 0.013(2) C109 0.082(4) 0.074(4) 0.044(3) 0.022(3) 0.013(2) 0.032(3) C110 0.059(3) 0.062(3) 0.056(4) 0.023(3) 0.017(2) 0.033(3) C111 0.035(2) 0.033(2) 0.034(2) 0.009(2) 0.0080(17) 0.0112(17) C112 0.0306(19) 0.035(2) 0.041(3) 0.011(2) 0.0100(17) 0.0084(18) C113 0.034(2) 0.039(3) 0.036(3) 0.011(2) 0.0086(17) 0.0095(18) C114 0.044(2) 0.036(3) 0.038(3) 0.014(2) 0.0113(19) 0.0083(19) C115 0.068(3) 0.052(4) 0.047(3) 0.024(3) 0.021(3) 0.011(3) C116 0.053(3) 0.043(3) 0.043(3) 0.011(2) 0.016(2) 0.011(2) C117 0.046(2) 0.043(2) 0.034(2) 0.0078(18) 0.0091(16) 0.0054(17) C118 0.065(3) 0.059(3) 0.042(3) 0.010(2) 0.021(2) 0.023(2) C119 0.074(3) 0.052(3) 0.038(3) 0.004(2) 0.004(2) -0.002(2) C120 0.062(3) 0.065(3) 0.036(3) 0.006(2) 0.018(2) 0.015(3) Cl12 0.0989(11) 0.0407(8) 0.0713(11) 0.0082(7) 0.0214(8) 0.0284(7) F201 0.081(2) 0.049(2) 0.070(2) 0.0164(17) 0.0249(16) -0.0069(15) F202 0.0577(16) 0.055(2) 0.084(2) 0.0207(18) 0.0359(16) 0.0298(15) F203 0.0505(16) 0.094(3) 0.073(2) 0.042(2) 0.0031(14) 0.0091(16) O201 0.0515(19) 0.042(2) 0.053(2) 0.0180(18) 0.0144(15) 0.0061(15) O202 0.063(2) 0.0457(17) 0.051(2) 0.0068(15) 0.0145(15) 0.0030(15) N201 0.0436(19) 0.040(2) 0.034(2) 0.0136(18) 0.0139(15) 0.0119(16) N202 0.0375(18) 0.043(2) 0.038(2) 0.0181(19) 0.0145(15) 0.0157(16) N203 0.0416(19) 0.042(2) 0.037(2) 0.0143(19) 0.0105(16) 0.0121(17) C201 0.042(2) 0.047(3) 0.033(3) 0.009(2) 0.0075(17) 0.018(2) C202 0.057(3) 0.033(3) 0.038(3) 0.009(2) 0.008(2) 0.014(2) C203 0.055(3) 0.041(3) 0.037(3) 0.008(2) 0.010(2) 0.001(2) C204 0.042(2) 0.060(4) 0.052(3) 0.018(3) 0.019(2) 0.006(2) C205 0.043(2) 0.044(3) 0.046(3) 0.012(2) 0.015(2) 0.017(2) C206 0.037(2) 0.037(3) 0.032(2) 0.012(2) 0.0086(17) 0.0113(18) C207 0.047(2) 0.040(3) 0.033(3) 0.014(2) 0.0167(18) 0.016(2) C208 0.052(3) 0.054(3) 0.041(3) 0.019(3) 0.013(2) 0.018(2) C209 0.093(4) 0.088(5) 0.040(3) 0.026(3) 0.021(3) 0.041(4) C210 0.079(4) 0.087(5) 0.061(4) 0.029(3) 0.023(3) 0.057(3) C211 0.031(2) 0.039(3) 0.037(3) 0.016(2) 0.0132(17) 0.0147(18) C212 0.0303(19) 0.036(2) 0.043(3) 0.017(2) 0.0120(17) 0.0104(17) C213 0.034(2) 0.038(3) 0.041(3) 0.012(2) 0.0097(18) 0.0131(18) C214 0.046(2) 0.035(3) 0.039(3) 0.013(2) 0.0101(19) 0.011(2) C215 0.070(3) 0.053(4) 0.066(4) 0.034(3) 0.033(3) 0.016(3) C216 0.037(2) 0.038(3) 0.043(3) 0.010(2) 0.0073(18) 0.0132(19) O203 0.0496(17) 0.0532(19) 0.0461(19) 0.0216(15) 0.0118(13) 0.0148(15) O204 0.060(2) 0.081(3) 0.069(3) 0.026(2) 0.0304(18) 0.0266(19) C217 0.042(2) 0.051(2) 0.039(2) 0.0082(19) 0.0082(16) 0.0181(18) C218 0.046(2) 0.042(2) 0.042(2) 0.0103(19) 0.0067(17) 0.0061(18) C219 0.101(4) 0.051(3) 0.048(3) 0.009(2) 0.027(3) 0.034(3) C220 0.051(3) 0.041(2) 0.033(2) 0.0050(19) 0.0072(18) 0.0066(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C112 O101 C115 117.9(4) . . ? C120 O103 H103 115(4) . . ? C106 N101 C107 117.2(4) . . ? C111 N101 C106 119.9(4) . . ? C111 N101 C107 122.9(4) . . ? C112 N102 C111 117.9(4) . . ? C114 N103 C113 120.0(4) . . ? C102 C101 H101 120.1 . . ? C106 C101 H101 120.1 . . ? C106 C101 C102 119.7(4) . . ? C101 C102 Cl11 120.9(4) . . ? C103 C102 Cl11 120.1(4) . . ? C103 C102 C101 119.0(4) . . ? F101 C103 C102 118.8(5) . . ? F101 C103 C104 119.0(5) . . ? C104 C103 C102 122.2(4) . . ? C103 C104 H104 121.4 . . ? C105 C104 C103 117.2(4) . . ? C105 C104 H104 121.4 . . ? F102 C105 C104 117.7(4) . . ? F102 C105 C106 119.5(4) . . ? C104 C105 C106 122.7(5) . . ? C101 C106 N101 120.8(4) . . ? C105 C106 N101 119.9(4) . . ? C105 C106 C101 119.2(4) . . ? N101 C107 H10A 108.5 . . ? N101 C107 H10B 108.5 . . ? N101 C107 C108 115.1(4) . . ? H10A C107 H10B 107.5 . . ? C108 C107 H10A 108.5 . . ? C108 C107 H10B 108.5 . . ? F103 C108 C107 105.7(4) . . ? F103 C108 C109 106.3(4) . . ? F103 C108 C110 107.4(4) . . ? C109 C108 C107 109.7(4) . . ? C110 C108 C107 113.3(4) . . ? C110 C108 C109 113.9(4) . . ? C108 C109 H10C 109.5 . . ? C108 C109 H10D 109.5 . . ? C108 C109 H10E 109.5 . . ? H10C C109 H10D 109.5 . . ? H10C C109 H10E 109.5 . . ? H10D C109 H10E 109.5 . . ? C108 C110 H11A 109.5 . . ? C108 C110 H11B 109.5 . . ? C108 C110 H11C 109.5 . . ? H11A C110 H11B 109.5 . . ? H11A C110 H11C 109.5 . . ? H11B C110 H11C 109.5 . . ? N101 C111 C114 121.6(4) . . ? N102 C111 N101 117.8(4) . . ? N102 C111 C114 120.5(4) . . ? O101 C112 C113 118.0(4) . . ? N102 C112 O101 118.9(4) . . ? N102 C112 C113 123.1(4) . . ? N103 C113 C112 117.9(4) . . ? N103 C113 C116 116.6(4) . . ? C112 C113 C116 125.4(4) . . ? N103 C114 C111 120.5(4) . . ? N103 C114 H114 119.7 . . ? C111 C114 H114 119.7 . . ? O101 C115 H11D 109.5 . . ? O101 C115 H11E 109.5 . . ? O101 C115 H11F 109.5 . . ? H11D C115 H11E 109.5 . . ? H11D C115 H11F 109.5 . . ? H11E C115 H11F 109.5 . . ? O102 C116 C113 121.4(4) . . ? O102 C116 C117 121.5(4) . . ? C113 C116 C117 117.0(4) . . ? C116 C117 H117 116.4 . . ? C116 C117 C118 118.9(4) . . ? C118 C117 H117 116.4 . . ? C119 C117 C116 117.1(4) . . ? C119 C117 H117 116.4 . . ? C119 C117 C118 59.9(3) . . ? C117 C118 H118 116.0 . . ? C119 C118 C117 59.1(3) . . ? C119 C118 H118 116.0 . . ? C120 C118 C117 118.9(4) . . ? C120 C118 H118 116.0 . . ? C120 C118 C119 119.0(5) . . ? C117 C119 C118 61.1(3) . . ? C117 C119 H11G 117.7 . . ? C117 C119 H11H 117.7 . . ? C118 C119 H11G 117.7 . . ? C118 C119 H11H 117.7 . . ? H11G C119 H11H 114.8 . . ? O103 C120 C118 113.0(5) . . ? O104 C120 O103 124.3(6) . . ? O104 C120 C118 122.7(5) . . ? C212 O201 C215 117.2(4) . . ? C206 N201 C207 116.4(4) . . ? C211 N201 C206 121.5(4) . . ? C211 N201 C207 122.1(4) . . ? C212 N202 C211 117.9(4) . . ? C214 N203 C213 119.8(4) . . ? C202 C201 H201 119.9 . . ? C202 C201 C206 120.2(4) . . ? C206 C201 H201 119.9 . . ? C201 C202 Cl12 120.3(4) . . ? C203 C202 Cl12 120.1(4) . . ? C203 C202 C201 119.6(4) . . ? F201 C203 C202 119.5(5) . . ? F201 C203 C204 117.8(5) . . ? C202 C203 C204 122.7(5) . . ? C203 C204 H204 121.5 . . ? C203 C204 C205 116.9(5) . . ? C205 C204 H204 121.5 . . ? F202 C205 C204 118.7(4) . . ? F202 C205 C206 118.3(4) . . ? C204 C205 C206 123.0(5) . . ? C201 C206 N201 121.7(4) . . ? C205 C206 N201 120.6(4) . . ? C205 C206 C201 117.6(4) . . ? N201 C207 H20A 108.5 . . ? N201 C207 H20B 108.5 . . ? N201 C207 C208 115.2(4) . . ? H20A C207 H20B 107.5 . . ? C208 C207 H20A 108.5 . . ? C208 C207 H20B 108.5 . . ? F203 C208 C207 107.3(4) . . ? F203 C208 C209 107.1(4) . . ? F203 C208 C210 106.4(4) . . ? C207 C208 C210 113.7(4) . . ? C209 C208 C207 109.5(4) . . ? C209 C208 C210 112.4(5) . . ? C208 C209 H20C 109.5 . . ? C208 C209 H20D 109.5 . . ? C208 C209 H20E 109.5 . . ? H20C C209 H20D 109.5 . . ? H20C C209 H20E 109.5 . . ? H20D C209 H20E 109.5 . . ? C208 C210 H21A 109.5 . . ? C208 C210 H21B 109.5 . . ? C208 C210 H21C 109.5 . . ? H21A C210 H21B 109.5 . . ? H21A C210 H21C 109.5 . . ? H21B C210 H21C 109.5 . . ? N201 C211 C214 121.8(4) . . ? N202 C211 N201 118.1(4) . . ? N202 C211 C214 120.1(4) . . ? O201 C212 C213 118.9(4) . . ? N202 C212 O201 118.1(4) . . ? N202 C212 C213 122.9(4) . . ? N203 C213 C212 118.0(4) . . ? N203 C213 C216 117.3(4) . . ? C212 C213 C216 124.8(4) . . ? N203 C214 C211 121.2(4) . . ? N203 C214 H214 119.4 . . ? C211 C214 H214 119.4 . . ? O201 C215 H21D 109.5 . . ? O201 C215 H21E 109.5 . . ? O201 C215 H21F 109.5 . . ? H21D C215 H21E 109.5 . . ? H21D C215 H21F 109.5 . . ? H21E C215 H21F 109.5 . . ? O202 C216 C213 121.4(4) . . ? O202 C216 C217 122.0(4) . . ? C217 C216 C213 116.6(4) . . ? C220 O203 H203 114(4) . . ? C216 C217 H217 116.7 . . ? C216 C217 C218 117.2(4) . . ? C216 C217 C219 118.3(4) . . ? C218 C217 H217 116.7 . . ? C219 C217 H217 116.7 . . ? C219 C217 C218 58.9(3) . . ? C217 C218 H218 116.5 . . ? C219 C218 C217 59.7(3) . . ? C219 C218 H218 116.5 . . ? C220 C218 C217 116.5(4) . . ? C220 C218 H218 116.5 . . ? C220 C218 C219 118.9(4) . . ? C217 C219 H21G 117.6 . . ? C217 C219 H21H 117.6 . . ? C218 C219 C217 61.4(3) . . ? C218 C219 H21G 117.6 . . ? C218 C219 H21H 117.6 . . ? H21G C219 H21H 114.7 . . ? O203 C220 C218 111.3(4) . . ? O204 C220 O203 123.6(5) . . ? O204 C220 C218 125.1(5) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C102 1.706(5) . ? F101 C103 1.342(5) . ? F102 C105 1.337(5) . ? F103 C108 1.418(5) . ? O101 C112 1.329(5) . ? O101 C115 1.431(6) . ? O102 C116 1.212(6) . ? O103 C120 1.318(6) . ? O103 H103 0.86(3) . ? O104 C120 1.194(6) . ? N101 C106 1.426(6) . ? N101 C107 1.450(6) . ? N101 C111 1.362(5) . ? N102 C111 1.330(5) . ? N102 C112 1.309(6) . ? N103 C113 1.334(6) . ? N103 C114 1.318(6) . ? C101 H101 0.9300 . ? C101 C102 1.383(7) . ? C101 C106 1.375(7) . ? C102 C103 1.375(7) . ? C103 C104 1.371(8) . ? C104 H104 0.9300 . ? C104 C105 1.364(7) . ? C105 C106 1.367(6) . ? C107 H10A 0.9700 . ? C107 H10B 0.9700 . ? C107 C108 1.520(6) . ? C108 C109 1.500(8) . ? C108 C110 1.493(8) . ? C109 H10C 0.9600 . ? C109 H10D 0.9600 . ? C109 H10E 0.9600 . ? C110 H11A 0.9600 . ? C110 H11B 0.9600 . ? C110 H11C 0.9600 . ? C111 C114 1.396(6) . ? C112 C113 1.401(6) . ? C113 C116 1.473(7) . ? C114 H114 0.9300 . ? C115 H11D 0.9600 . ? C115 H11E 0.9600 . ? C115 H11F 0.9600 . ? C116 C117 1.481(7) . ? C117 H117 0.9800 . ? C117 C118 1.507(6) . ? C117 C119 1.478(6) . ? C118 H118 0.9800 . ? C118 C119 1.490(7) . ? C118 C120 1.478(7) . ? C119 H11G 0.9700 . ? C119 H11H 0.9700 . ? Cl12 C202 1.719(5) . ? F201 C203 1.344(6) . ? F202 C205 1.340(5) . ? F203 C208 1.399(6) . ? O201 C212 1.333(6) . ? O201 C215 1.431(7) . ? O202 C216 1.206(5) . ? N201 C206 1.411(6) . ? N201 C207 1.465(6) . ? N201 C211 1.358(6) . ? N202 C211 1.327(5) . ? N202 C212 1.316(6) . ? N203 C213 1.341(6) . ? N203 C214 1.303(6) . ? C201 H201 0.9300 . ? C201 C202 1.372(7) . ? C201 C206 1.381(7) . ? C202 C203 1.354(7) . ? C203 C204 1.354(8) . ? C204 H204 0.9300 . ? C204 C205 1.372(7) . ? C205 C206 1.376(6) . ? C207 H20A 0.9700 . ? C207 H20B 0.9700 . ? C207 C208 1.500(6) . ? C208 C209 1.498(8) . ? C208 C210 1.502(8) . ? C209 H20C 0.9600 . ? C209 H20D 0.9600 . ? C209 H20E 0.9600 . ? C210 H21A 0.9600 . ? C210 H21B 0.9600 . ? C210 H21C 0.9600 . ? C211 C214 1.399(6) . ? C212 C213 1.394(6) . ? C213 C216 1.482(7) . ? C214 H214 0.9300 . ? C215 H21D 0.9600 . ? C215 H21E 0.9600 . ? C215 H21F 0.9600 . ? C216 C217 1.469(7) . ? O203 C220 1.323(6) . ? O203 H203 0.86(3) . ? O204 C220 1.193(6) . ? C217 H217 0.9800 . ? C217 C218 1.516(5) . ? C217 C219 1.490(6) . ? C218 H218 0.9800 . ? C218 C219 1.479(7) . ? C218 C220 1.474(6) . ? C219 H21G 0.9700 . ? C219 H21H 0.9700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O203 H203 N103 0.86(3) 1.90(3) 2.729(5) 161(6) 1_454 O103 H103 N203 0.86(3) 2.00(3) 2.859(5) 176(5) 1_656 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl11 C102 C103 F101 -0.6(6) . . . . ? Cl11 C102 C103 C104 179.3(4) . . . . ? F101 C103 C104 C105 -179.9(4) . . . . ? F102 C105 C106 N101 -4.6(7) . . . . ? F102 C105 C106 C101 179.1(4) . . . . ? O101 C112 C113 N103 -176.9(4) . . . . ? O101 C112 C113 C116 6.0(7) . . . . ? O102 C116 C117 C118 58.2(6) . . . . ? O102 C116 C117 C119 -10.6(7) . . . . ? N101 C107 C108 F103 -51.9(5) . . . . ? N101 C107 C108 C109 -166.1(4) . . . . ? N101 C107 C108 C110 65.4(5) . . . . ? N101 C111 C114 N103 -178.2(4) . . . . ? N102 C111 C114 N103 2.3(6) . . . . ? N102 C112 C113 N103 2.2(6) . . . . ? N102 C112 C113 C116 -174.9(4) . . . . ? N103 C113 C116 O102 -151.2(5) . . . . ? N103 C113 C116 C117 29.0(6) . . . . ? C101 C102 C103 F101 179.3(4) . . . . ? C101 C102 C103 C104 -0.8(7) . . . . ? C102 C101 C106 N101 -176.0(4) . . . . ? C102 C101 C106 C105 0.2(7) . . . . ? C102 C103 C104 C105 0.2(7) . . . . ? C103 C104 C105 F102 -179.3(4) . . . . ? C103 C104 C105 C106 0.6(7) . . . . ? C104 C105 C106 N101 175.5(4) . . . . ? C104 C105 C106 C101 -0.8(7) . . . . ? C106 N101 C107 C108 76.9(5) . . . . ? C106 N101 C111 N102 -170.9(4) . . . . ? C106 N101 C111 C114 9.5(6) . . . . ? C106 C101 C102 Cl11 -179.5(3) . . . . ? C106 C101 C102 C103 0.5(7) . . . . ? C107 N101 C106 C101 66.5(5) . . . . ? C107 N101 C106 C105 -109.8(5) . . . . ? C107 N101 C111 N102 7.5(6) . . . . ? C107 N101 C111 C114 -172.0(4) . . . . ? C111 N101 C106 C101 -115.0(5) . . . . ? C111 N101 C106 C105 68.8(5) . . . . ? C111 N101 C107 C108 -101.6(5) . . . . ? C111 N102 C112 O101 -179.4(4) . . . . ? C111 N102 C112 C113 1.5(6) . . . . ? C112 N102 C111 N101 176.8(4) . . . . ? C112 N102 C111 C114 -3.7(6) . . . . ? C112 C113 C116 O102 25.9(8) . . . . ? C112 C113 C116 C117 -153.9(4) . . . . ? C113 N103 C114 C111 1.6(6) . . . . ? C113 C116 C117 C118 -122.1(5) . . . . ? C113 C116 C117 C119 169.1(4) . . . . ? C114 N103 C113 C112 -3.7(6) . . . . ? C114 N103 C113 C116 173.7(4) . . . . ? C115 O101 C112 N102 0.9(6) . . . . ? C115 O101 C112 C113 -179.9(4) . . . . ? C116 C117 C118 C119 -106.4(5) . . . . ? C116 C117 C118 C120 145.3(4) . . . . ? C116 C117 C119 C118 109.3(5) . . . . ? C117 C118 C120 O103 35.5(6) . . . . ? C117 C118 C120 O104 -145.6(5) . . . . ? C119 C117 C118 C120 -108.3(5) . . . . ? C119 C118 C120 O103 -33.0(6) . . . . ? C119 C118 C120 O104 145.8(5) . . . . ? C120 C118 C119 C117 108.2(5) . . . . ? Cl12 C202 C203 F201 -0.4(7) . . . . ? Cl12 C202 C203 C204 -179.7(4) . . . . ? F201 C203 C204 C205 -179.0(4) . . . . ? F202 C205 C206 N201 4.7(7) . . . . ? F202 C205 C206 C201 -179.3(4) . . . . ? O201 C212 C213 N203 -179.5(4) . . . . ? O201 C212 C213 C216 0.6(6) . . . . ? O202 C216 C217 C218 53.2(6) . . . . ? O202 C216 C217 C219 -14.3(6) . . . . ? N201 C207 C208 F203 54.3(5) . . . . ? N201 C207 C208 C209 170.2(5) . . . . ? N201 C207 C208 C210 -63.2(6) . . . . ? N201 C211 C214 N203 179.7(4) . . . . ? N202 C211 C214 N203 -1.5(6) . . . . ? N202 C212 C213 N203 -1.6(6) . . . . ? N202 C212 C213 C216 178.5(4) . . . . ? N203 C213 C216 O202 -156.7(4) . . . . ? N203 C213 C216 C217 20.8(5) . . . . ? C201 C202 C203 F201 179.8(4) . . . . ? C201 C202 C203 C204 0.5(8) . . . . ? C202 C201 C206 N201 174.8(4) . . . . ? C202 C201 C206 C205 -1.1(7) . . . . ? C202 C203 C204 C205 0.3(8) . . . . ? C203 C204 C205 F202 179.7(5) . . . . ? C203 C204 C205 C206 -1.6(8) . . . . ? C204 C205 C206 N201 -174.0(4) . . . . ? C204 C205 C206 C201 2.0(7) . . . . ? C206 N201 C207 C208 -75.7(5) . . . . ? C206 N201 C211 N202 171.6(4) . . . . ? C206 N201 C211 C214 -9.5(6) . . . . ? C206 C201 C202 Cl12 -179.9(3) . . . . ? C206 C201 C202 C203 -0.1(7) . . . . ? C207 N201 C206 C201 -66.1(5) . . . . ? C207 N201 C206 C205 109.7(5) . . . . ? C207 N201 C211 N202 -6.6(6) . . . . ? C207 N201 C211 C214 172.3(4) . . . . ? C211 N201 C206 C201 115.6(5) . . . . ? C211 N201 C206 C205 -68.6(6) . . . . ? C211 N201 C207 C208 102.6(5) . . . . ? C211 N202 C212 O201 177.3(3) . . . . ? C211 N202 C212 C213 -0.6(6) . . . . ? C212 N202 C211 N201 -179.0(4) . . . . ? C212 N202 C211 C214 2.1(6) . . . . ? C212 C213 C216 O202 23.1(6) . . . . ? C212 C213 C216 C217 -159.3(4) . . . . ? C213 N203 C214 C211 -0.9(6) . . . . ? C213 C216 C217 C218 -124.3(4) . . . . ? C213 C216 C217 C219 168.2(4) . . . . ? C214 N203 C213 C212 2.3(6) . . . . ? C214 N203 C213 C216 -177.8(4) . . . . ? C215 O201 C212 N202 -1.4(6) . . . . ? C215 O201 C212 C213 176.5(4) . . . . ? C216 C217 C218 C219 -108.2(5) . . . . ? C216 C217 C218 C220 142.2(4) . . . . ? C216 C217 C219 C218 106.3(4) . . . . ? C217 C218 C220 O203 -132.0(4) . . . . ? C217 C218 C220 O204 47.3(6) . . . . ? C219 C217 C218 C220 -109.5(5) . . . . ? C219 C218 C220 O203 159.7(4) . . . . ? C219 C218 C220 O204 -21.0(7) . . . . ? C220 C218 C219 C217 105.5(4) . . . . ?