#------------------------------------------------------------------------------ #$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $ #$Revision: 249721 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240202.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_7240202 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 geom _atom_sites_solution_primary iterative _audit_creation_date 2016-02-19 _audit_creation_method ; Olex2 1.2-alpha (compiled 2016.02.16 svn.r3264 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2020-02-07 deposited with the CCDC. 2020-03-24 downloaded from the CCDC. ; _cell_angle_alpha 107.504(4) _cell_angle_beta 100.890(5) _cell_angle_gamma 104.746(5) _cell_formula_units_Z 2 _cell_length_a 9.4219(6) _cell_length_b 11.2659(6) _cell_length_c 11.5862(6) _cell_measurement_reflns_used 5840 _cell_measurement_temperature 410(2) _cell_measurement_theta_max 28.6190 _cell_measurement_theta_min 2.2750 _cell_volume 1086.25(12) _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 410(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 0.999 _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 72.00 120.00 129 2 \w -58.00 71.00 1.00 10.00 -- -19.00 72.00 -90.00 129 3 \w -94.00 20.00 1.00 10.00 -- -19.00 -72.00-180.00 114 4 \w -69.00 20.00 1.00 10.00 -- -19.00 -72.00 0.00 89 5 \w -58.00 60.00 1.00 10.00 -- -19.00 72.00 0.00 118 6 \w -44.00 24.00 1.00 10.00 -- -19.00 0.00 150.00 68 7 \w -87.00 15.00 1.00 10.00 -- -19.00 0.00 -30.00 102 8 \w -48.00 4.00 1.00 10.00 -- -19.00 72.00-180.00 52 9 \w -15.00 4.00 1.00 10.00 -- -19.00 -72.00 60.00 19 10 \w -2.00 20.00 1.00 10.00 -- -19.00 -72.00-150.00 22 11 \w -58.00 -47.00 1.00 10.00 -- -19.00 72.00-150.00 11 12 \w -44.00 -34.00 1.00 10.00 -- -19.00 72.00 60.00 10 ; _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 0.0585375000 _diffrn_orient_matrix_UB_12 -0.0021013000 _diffrn_orient_matrix_UB_13 0.0470867000 _diffrn_orient_matrix_UB_21 -0.0324374000 _diffrn_orient_matrix_UB_22 0.0286697000 _diffrn_orient_matrix_UB_23 0.0471287000 _diffrn_orient_matrix_UB_31 -0.0461374000 _diffrn_orient_matrix_UB_32 -0.0638233000 _diffrn_orient_matrix_UB_33 -0.0073856000 _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 0.0391 _diffrn_reflns_av_unetI/netI 0.0700 _diffrn_reflns_Laue_measured_fraction_full 0.999 _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 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 22314 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 28.698 _diffrn_reflns_theta_min 3.134 _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 0.233 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65738 _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 1.400 _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 0.229 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details ; Flack x determined using 1624 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 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 566 _refine_ls_number_reflns 11088 _refine_ls_number_restraints 483 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.1755 _refine_ls_R_factor_gt 0.0692 _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^)+(0.0841P)^2^+0.0097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1515 _refine_ls_wR_factor_ref 0.2004 _reflns_Friedel_coverage 0.981 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.978 _reflns_number_gt 4808 _reflns_number_total 11088 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00276c2.cif _cod_data_source_block 2016scas0001_r_410k _cod_original_cell_volume 1086.25(11) _cod_database_code 7240202 _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 90.42 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.80 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 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 Me refined with riding coordinates: C115(H11D,H11E,H11F) 3.d Aromatic/amide H refined with riding coordinates: C101(H101), C104(H104), C114(H114), C201(H201), C204(H204), C214(H214) 3.e Idealised Me refined as rotating group: C109(H10C,H10D,H10E), C110(H11A,H11B,H11C), C209(H20C,H20D,H20E), C210(H21D, H21E,H21F), C215(H21A,H21B,H21C) 3.f Idealised tetrahedral OH refined as rotating group: O103(H103), O203(H203) ; _shelx_res_file ; 2016scas0001_r_410k.res created by SHELXL-2014/7 TITL 2016scas0001_R_410K in P1 #1 REM reset to P1 #1 CELL 0.71073 9.421889 11.265887 11.586234 107.5039 100.8901 104.7458 ZERR 2 0.000589 0.000555 0.000576 0.0044 0.0048 0.0048 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,1+Y,1+Z RIGU L.S. 4 0 0 PLAN 20 TEMP 137(2) HTAB O203 N103_$1 HTAB O103 O202_$2 fmap 2 53 MORE -1 BOND $H ACTA 52 CONF SHEL 7 0.74 REM REM REM WGHT 0.084100 0.009700 FVAR 8.47243 CL11 3 0.400411 -0.401018 -0.006722 11.00000 0.17342 0.07379 = 0.11041 0.02316 0.04012 0.04584 F101 4 0.128571 -0.362437 0.056228 11.00000 0.12516 0.10406 = 0.11248 0.04624 0.02793 -0.00384 F102 4 0.267171 0.086156 0.133052 11.00000 0.10154 0.10419 = 0.11638 0.03840 0.05329 0.05489 F103 4 0.288036 0.025628 -0.145396 11.00000 0.09848 0.14439 = 0.11719 0.06272 -0.01728 -0.00044 O101 6 0.826060 0.531934 0.279734 11.00000 0.09235 0.07673 = 0.07614 0.04277 0.01720 0.00678 O102 6 0.913343 0.623405 0.533303 11.00000 0.18218 0.07145 = 0.09333 0.01121 0.05628 0.00477 O103 6 0.740996 0.701232 0.921992 11.00000 0.22606 0.10229 = 0.13085 0.03231 0.11325 0.03927 AFIX 147 H103 2 0.804340 0.766562 0.922233 11.00000 -1.50000 AFIX 0 O104 6 0.701882 0.489364 0.860219 11.00000 0.23610 0.09559 = 0.10217 0.04403 0.06304 -0.00396 N101 5 0.536439 0.094786 0.070223 11.00000 0.06850 0.07184 = 0.04753 0.02332 0.02075 0.02232 N102 5 0.684755 0.312390 0.176191 11.00000 0.06308 0.06333 = 0.05125 0.02779 0.01606 0.02110 N103 5 0.688131 0.287658 0.405044 11.00000 0.07453 0.05534 = 0.04879 0.02096 0.01837 0.02086 C101 1 0.463503 -0.141952 0.034245 11.00000 0.07648 0.07040 = 0.05083 0.01614 0.01535 0.02870 AFIX 43 H101 2 0.553666 -0.144341 0.013516 11.00000 -1.20000 AFIX 0 C102 1 0.359289 -0.256757 0.030709 11.00000 0.09768 0.06204 = 0.05180 0.01039 0.01231 0.01855 C103 1 0.226785 -0.249573 0.060202 11.00000 0.08543 0.08168 = 0.06307 0.02253 0.01697 0.00560 C104 1 0.195691 -0.137372 0.091925 11.00000 0.07150 0.10703 = 0.07762 0.03529 0.03232 0.02574 AFIX 43 H104 2 0.103791 -0.135383 0.109435 11.00000 -1.20000 AFIX 0 C105 1 0.300138 -0.025965 0.098318 11.00000 0.08054 0.07956 = 0.06858 0.02645 0.03053 0.03056 C106 1 0.432594 -0.023714 0.068812 11.00000 0.06016 0.06400 = 0.04360 0.01219 0.01276 0.02042 C107 1 0.551453 0.102208 -0.051472 11.00000 0.08561 0.09526 = 0.04874 0.02491 0.02573 0.02829 AFIX 23 H10A 2 0.558778 0.019435 -0.102563 11.00000 -1.20000 H10B 2 0.646586 0.171207 -0.036064 11.00000 -1.20000 AFIX 0 C108 1 0.421063 0.129516 -0.126706 11.00000 0.09138 0.10368 = 0.05393 0.03279 0.00888 0.02003 C109 1 0.440215 0.120282 -0.254975 11.00000 0.18991 0.20058 = 0.06296 0.06741 0.03575 0.08619 AFIX 137 H10C 2 0.436561 0.032502 -0.300921 11.00000 -1.50000 H10D 2 0.537167 0.182134 -0.245100 11.00000 -1.50000 H10E 2 0.359120 0.140324 -0.300634 11.00000 -1.50000 AFIX 0 C110 1 0.396797 0.255031 -0.059721 11.00000 0.10648 0.12795 = 0.08621 0.04959 0.01424 0.05631 AFIX 137 H11A 2 0.311865 0.264343 -0.112488 11.00000 -1.50000 H11B 2 0.487485 0.328202 -0.041239 11.00000 -1.50000 H11C 2 0.375426 0.253315 0.017670 11.00000 -1.50000 AFIX 0 C111 1 0.611902 0.197904 0.180718 11.00000 0.05334 0.06399 = 0.05121 0.02784 0.01720 0.02737 C112 1 0.755572 0.413740 0.283530 11.00000 0.06052 0.06147 = 0.06619 0.03430 0.01831 0.01554 C113 1 0.759040 0.404877 0.401882 11.00000 0.06461 0.05526 = 0.05721 0.02467 0.02339 0.02395 C114 1 0.615178 0.186992 0.299035 11.00000 0.08772 0.05035 = 0.04936 0.02311 0.02133 0.01735 AFIX 43 H114 2 0.564130 0.106075 0.301945 11.00000 -1.20000 AFIX 0 C115 1 0.812592 0.541259 0.155559 11.00000 0.12204 0.10017 = 0.09906 0.06779 0.03427 0.01609 AFIX 33 H11D 2 0.867306 0.629769 0.165275 11.00000 -1.50000 H11E 2 0.855114 0.481324 0.107573 11.00000 -1.50000 H11F 2 0.706488 0.518823 0.112069 11.00000 -1.50000 AFIX 0 C116 1 0.835984 0.515884 0.525338 11.00000 0.07870 0.05784 = 0.06481 0.01769 0.01913 0.01734 C117 1 0.818437 0.494066 0.641541 11.00000 0.14627 0.06364 = 0.06037 0.01604 0.01198 0.02427 AFIX 13 H117 2 0.738758 0.412427 0.629450 11.00000 -1.20000 AFIX 0 C118 1 0.847320 0.608485 0.760207 11.00000 0.12628 0.07846 = 0.07063 0.01524 0.03539 0.02454 AFIX 13 H118 2 0.879571 0.696340 0.755516 11.00000 -1.20000 AFIX 0 C119 1 0.953068 0.538437 0.749113 11.00000 0.19725 0.24226 = 0.05688 0.01351 0.01142 0.13166 AFIX 23 H11G 2 0.957574 0.482767 0.798391 11.00000 -1.20000 H11H 2 1.051034 0.582567 0.740425 11.00000 -1.20000 AFIX 0 C120 1 0.758527 0.592739 0.848709 11.00000 0.14192 0.08147 = 0.07029 0.01937 0.03175 0.01251 CL12 3 0.248448 0.908030 0.418849 11.00000 0.35489 0.07101 = 0.10410 0.01844 0.01022 0.08730 F201 4 0.537082 0.897933 0.359617 11.00000 0.24123 0.09372 = 0.12694 0.04971 0.00520 -0.06079 F202 4 0.445399 0.451100 0.284633 11.00000 0.10376 0.12497 = 0.14570 0.05512 0.06081 0.05512 F203 4 0.425028 0.490955 0.550693 11.00000 0.09033 0.12324 = 0.13756 0.06533 0.00327 0.00972 O201 6 -0.128652 -0.009867 0.109746 11.00000 0.08709 0.06138 = 0.06922 0.02408 0.01868 0.01057 O202 6 -0.192524 -0.088144 -0.146379 11.00000 0.17504 0.07071 = 0.06900 0.02062 0.00338 0.00680 O203 6 -0.302004 0.153769 -0.426703 11.00000 0.12313 0.08319 = 0.07569 0.04377 0.03077 0.02649 AFIX 147 H203 2 -0.290617 0.206077 -0.463198 11.00000 -1.50000 AFIX 0 O204 6 -0.078237 0.150789 -0.453458 11.00000 0.12111 0.15039 = 0.15700 0.09362 0.06014 0.03810 N201 5 0.170822 0.421203 0.340672 11.00000 0.07236 0.04969 = 0.05596 0.01590 0.01975 0.01908 N202 5 0.014523 0.203693 0.222505 11.00000 0.06300 0.05324 = 0.05809 0.02330 0.01703 0.02197 N203 5 0.033758 0.245276 0.002861 11.00000 0.09174 0.06686 = 0.05561 0.02804 0.01478 0.02195 C201 1 0.215562 0.653838 0.378806 11.00000 0.10629 0.05413 = 0.05918 0.01068 0.00372 0.01988 AFIX 43 H201 2 0.123083 0.646436 0.398197 11.00000 -1.20000 AFIX 0 C202 1 0.304983 0.772578 0.383431 11.00000 0.16500 0.05325 = 0.06123 0.01465 -0.00354 0.01010 C203 1 0.441764 0.780972 0.356340 11.00000 0.14722 0.06370 = 0.06427 0.02557 -0.00792 -0.02462 C204 1 0.494882 0.675531 0.323567 11.00000 0.11586 0.10520 = 0.09716 0.03944 0.01955 -0.01177 AFIX 43 H204 2 0.587880 0.684095 0.304907 11.00000 -1.20000 AFIX 0 C205 1 0.403173 0.557332 0.319969 11.00000 0.08035 0.07815 = 0.08869 0.03529 0.02432 0.00855 C206 1 0.262403 0.544909 0.345378 11.00000 0.07778 0.06133 = 0.05475 0.02518 0.01134 0.01278 C207 1 0.156133 0.406992 0.459846 11.00000 0.08510 0.05508 = 0.05110 0.01327 0.02551 0.02276 AFIX 23 H20A 2 0.064580 0.333249 0.441877 11.00000 -1.20000 H20B 2 0.142596 0.485919 0.512617 11.00000 -1.20000 AFIX 0 C208 1 0.293220 0.384607 0.534014 11.00000 0.07876 0.07714 = 0.06949 0.03130 0.02000 0.02141 C209 1 0.277956 0.395316 0.662279 11.00000 0.16984 0.13651 = 0.06900 0.04504 0.03334 0.06248 AFIX 137 H20C 2 0.260635 0.476441 0.701306 11.00000 -1.50000 H20D 2 0.370345 0.394141 0.713110 11.00000 -1.50000 H20E 2 0.193067 0.322259 0.654961 11.00000 -1.50000 AFIX 0 C210 1 0.320397 0.261020 0.466008 11.00000 0.11633 0.11242 = 0.10584 0.04587 0.02696 0.06553 AFIX 137 H21D 2 0.232647 0.186257 0.450119 11.00000 -1.50000 H21E 2 0.409030 0.254527 0.516918 11.00000 -1.50000 H21F 2 0.337014 0.262699 0.387195 11.00000 -1.50000 AFIX 0 C211 1 0.094185 0.321122 0.225327 11.00000 0.06397 0.05152 = 0.05069 0.01601 0.01505 0.02124 C212 1 -0.051731 0.108356 0.112192 11.00000 0.05620 0.05135 = 0.05928 0.01817 0.01496 0.02132 C213 1 -0.043395 0.123550 -0.003166 11.00000 0.07269 0.06158 = 0.05216 0.02097 0.01337 0.01942 C214 1 0.097093 0.341987 0.111878 11.00000 0.07440 0.06651 = 0.05963 0.02403 0.00905 0.01627 AFIX 43 H214 2 0.145106 0.426350 0.114824 11.00000 -1.20000 AFIX 0 C215 1 -0.132405 -0.025825 0.227224 11.00000 0.09855 0.07557 = 0.08841 0.04242 0.03160 0.01670 AFIX 137 H21A 2 -0.194276 -0.114417 0.211144 11.00000 -1.50000 H21B 2 -0.175331 0.035153 0.273159 11.00000 -1.50000 H21C 2 -0.030124 -0.008914 0.276167 11.00000 -1.50000 AFIX 0 C216 1 -0.106090 0.021098 -0.127668 11.00000 0.09895 0.07006 = 0.05477 0.01722 0.00822 0.03259 C217 1 -0.067224 0.053452 -0.235703 11.00000 0.09499 0.09761 = 0.05197 0.02308 0.01631 0.03780 AFIX 13 H217 2 0.018666 0.134394 -0.214303 11.00000 -1.20000 AFIX 0 C218 1 -0.197246 0.018758 -0.351248 11.00000 0.11778 0.05778 = 0.06582 0.02298 -0.00191 0.01133 AFIX 13 H218 2 -0.300306 -0.025903 -0.349610 11.00000 -1.20000 AFIX 0 C219 1 -0.090052 -0.055484 -0.354096 11.00000 0.26376 0.13704 = 0.06550 0.03682 0.04630 0.12091 AFIX 23 H21G 2 -0.017584 -0.041948 -0.402136 11.00000 -1.20000 H21H 2 -0.127374 -0.144890 -0.356145 11.00000 -1.20000 AFIX 0 C220 1 -0.184212 0.111962 -0.416281 11.00000 0.10563 0.06253 = 0.05698 0.01587 0.01231 0.00793 HKLF 4 REM 2016scas0001_R_410K in P1 #1 REM R1 = 0.0692 for 4808 Fo > 4sig(Fo) and 0.1755 for all 11088 data REM 566 parameters refined using 483 restraints END WGHT 0.0841 0.0097 REM Highest difference peak 0.229, deepest hole -0.168, 1-sigma level 0.037 Q1 1 0.2814 0.9247 0.4045 11.00000 0.05 0.23 Q2 1 0.8287 0.4324 0.8202 11.00000 0.05 0.22 Q3 1 0.5268 -0.3739 -0.0448 11.00000 0.05 0.20 Q4 1 0.1552 0.9286 0.4555 11.00000 0.05 0.19 Q5 1 0.9609 0.3779 0.8204 11.00000 0.05 0.19 Q6 1 0.7273 0.3933 0.8626 11.00000 0.05 0.19 Q7 1 0.7894 0.6162 0.5213 11.00000 0.05 0.17 Q8 1 0.9185 0.4790 0.6283 11.00000 0.05 0.16 Q9 1 -0.0847 0.1366 0.0468 11.00000 0.05 0.16 Q10 1 -0.0613 0.1855 -0.0129 11.00000 0.05 0.16 Q11 1 0.7552 0.3367 0.4217 11.00000 0.05 0.16 Q12 1 -0.2429 -0.1034 -0.1196 11.00000 0.05 0.16 Q13 1 0.8401 0.5191 0.3031 11.00000 0.05 0.16 Q14 1 0.3234 0.8950 0.4824 11.00000 0.05 0.15 Q15 1 -0.2089 0.0370 -0.2523 11.00000 0.05 0.14 Q16 1 0.3494 0.8232 0.3770 11.00000 0.05 0.14 Q17 1 -0.1213 0.1077 -0.4067 11.00000 0.05 0.13 Q18 1 -0.2135 0.1190 -0.4338 11.00000 0.05 0.13 Q19 1 -0.0941 0.0457 0.2945 11.00000 0.05 0.13 Q20 1 0.4652 -0.0647 0.0931 11.00000 0.05 0.13 ; _shelx_res_checksum 5334 _shelx_shelxl_version_number 2014/7 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 5.491 _oxdiff_exptl_absorpt_empirical_full_min 0.394 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 0.4004(4) -0.4010(2) -0.0067(2) 0.1210(9) Uani 1 1 d . U . . . F101 F 0.1286(6) -0.3624(5) 0.0562(5) 0.1218(18) Uani 1 1 d . U . . . F102 F 0.2672(5) 0.0862(5) 0.1331(5) 0.1004(14) Uani 1 1 d . U . . . F103 F 0.2880(6) 0.0256(6) -0.1454(5) 0.132(2) Uani 1 1 d . U . . . O101 O 0.8261(6) 0.5319(5) 0.2797(5) 0.0835(15) Uani 1 1 d . U . . . O102 O 0.9133(9) 0.6234(6) 0.5333(6) 0.125(3) Uani 1 1 d . U . . . O103 O 0.7410(11) 0.7012(6) 0.9220(7) 0.150(3) Uani 1 1 d . U . . . H103 H 0.8043 0.7666 0.9222 0.224 Uiso 1 1 calc GR . . . . O104 O 0.7019(10) 0.4894(6) 0.8602(6) 0.153(3) Uani 1 1 d . U . . . N101 N 0.5364(6) 0.0948(5) 0.0702(5) 0.0619(14) Uani 1 1 d . U . . . N102 N 0.6848(6) 0.3124(5) 0.1762(5) 0.0576(13) Uani 1 1 d . U . . . N103 N 0.6881(6) 0.2877(5) 0.4050(5) 0.0592(13) Uani 1 1 d . U . . . C101 C 0.4635(9) -0.1420(7) 0.0342(6) 0.0670(17) Uani 1 1 d . U . . . H101 H 0.5537 -0.1443 0.0135 0.080 Uiso 1 1 calc R . . . . C102 C 0.3593(10) -0.2568(7) 0.0307(6) 0.0761(19) Uani 1 1 d . U . . . C103 C 0.2268(10) -0.2496(8) 0.0602(7) 0.083(2) Uani 1 1 d . U . . . C104 C 0.1957(9) -0.1374(9) 0.0919(7) 0.084(2) Uani 1 1 d . U . . . H104 H 0.1038 -0.1354 0.1094 0.101 Uiso 1 1 calc R . . . . C105 C 0.3001(9) -0.0260(8) 0.0983(7) 0.0743(19) Uani 1 1 d . U . . . C106 C 0.4326(8) -0.0237(6) 0.0688(6) 0.0581(15) Uani 1 1 d . U . . . C107 C 0.5515(9) 0.1022(8) -0.0515(6) 0.076(2) Uani 1 1 d . U . . . H10A H 0.5588 0.0194 -0.1026 0.092 Uiso 1 1 calc R . . . . H10B H 0.6466 0.1712 -0.0361 0.092 Uiso 1 1 calc R . . . . C108 C 0.4211(10) 0.1295(9) -0.1267(7) 0.086(2) Uani 1 1 d . U . . . C109 C 0.4402(15) 0.1203(13) -0.2550(9) 0.142(4) Uani 1 1 d . U . . . H10C H 0.4366 0.0325 -0.3009 0.213 Uiso 1 1 calc GR . . . . H10D H 0.5372 0.1821 -0.2451 0.213 Uiso 1 1 calc GR . . . . H10E H 0.3591 0.1403 -0.3006 0.213 Uiso 1 1 calc GR . . . . C110 C 0.3968(11) 0.2550(10) -0.0597(8) 0.103(3) Uani 1 1 d . U . . . H11A H 0.3119 0.2643 -0.1125 0.154 Uiso 1 1 calc GR . . . . H11B H 0.4875 0.3282 -0.0412 0.154 Uiso 1 1 calc GR . . . . H11C H 0.3754 0.2533 0.0177 0.154 Uiso 1 1 calc GR . . . . C111 C 0.6119(7) 0.1979(6) 0.1807(6) 0.0526(14) Uani 1 1 d . U . . . C112 C 0.7556(8) 0.4137(7) 0.2835(7) 0.0610(16) Uani 1 1 d . U . . . C113 C 0.7590(7) 0.4049(6) 0.4019(6) 0.0564(15) Uani 1 1 d . U . . . C114 C 0.6152(8) 0.1870(6) 0.2990(6) 0.0622(17) Uani 1 1 d . U . . . H114 H 0.5641 0.1061 0.3019 0.075 Uiso 1 1 calc R . . . . C115 C 0.8126(11) 0.5413(9) 0.1556(8) 0.103(3) Uani 1 1 d . U . . . H11D H 0.8673 0.6298 0.1653 0.155 Uiso 1 1 calc R . . . . H11E H 0.8551 0.4813 0.1076 0.155 Uiso 1 1 calc R . . . . H11F H 0.7065 0.5188 0.1121 0.155 Uiso 1 1 calc R . . . . C116 C 0.8360(9) 0.5159(7) 0.5253(7) 0.0696(18) Uani 1 1 d . U . . . C117 C 0.8184(12) 0.4941(8) 0.6415(7) 0.097(3) Uani 1 1 d . U . . . H117 H 0.7388 0.4124 0.6295 0.116 Uiso 1 1 calc R . . . . C118 C 0.8473(11) 0.6085(8) 0.7602(7) 0.096(2) Uani 1 1 d . U . . . H118 H 0.8796 0.6963 0.7555 0.115 Uiso 1 1 calc R . . . . C119 C 0.9531(16) 0.5384(16) 0.7491(9) 0.167(5) Uani 1 1 d . U . . . H11G H 0.9576 0.4828 0.7984 0.201 Uiso 1 1 calc R . . . . H11H H 1.0510 0.5826 0.7404 0.201 Uiso 1 1 calc R . . . . C120 C 0.7585(11) 0.5927(9) 0.8487(7) 0.105(3) Uani 1 1 d . U . . . Cl12 Cl 0.2484(5) 0.9080(2) 0.4188(3) 0.1850(18) Uani 1 1 d . U . . . F201 F 0.5371(10) 0.8979(5) 0.3596(6) 0.183(3) Uani 1 1 d . U . . . F202 F 0.4454(6) 0.4511(6) 0.2846(5) 0.1163(17) Uani 1 1 d . U . . . F203 F 0.4250(6) 0.4910(5) 0.5507(6) 0.1224(18) Uani 1 1 d . U . . . O201 O -0.1287(6) -0.0099(4) 0.1097(4) 0.0760(13) Uani 1 1 d . U . . . O202 O -0.1925(9) -0.0881(6) -0.1464(5) 0.118(2) Uani 1 1 d . U . . . O203 O -0.3020(7) 0.1538(5) -0.4267(5) 0.0917(14) Uani 1 1 d . U . . . H203 H -0.2906 0.2061 -0.4632 0.138 Uiso 1 1 calc GR . . . . O204 O -0.0782(8) 0.1508(7) -0.4535(7) 0.132(2) Uani 1 1 d . U . . . N201 N 0.1708(6) 0.4212(5) 0.3407(5) 0.0602(13) Uani 1 1 d . U . . . N202 N 0.0145(6) 0.2037(5) 0.2225(5) 0.0569(13) Uani 1 1 d . U . . . N203 N 0.0338(7) 0.2453(5) 0.0029(5) 0.0719(16) Uani 1 1 d . U . . . C201 C 0.2156(10) 0.6538(7) 0.3788(7) 0.080(2) Uani 1 1 d . U . . . H201 H 0.1231 0.6464 0.3982 0.096 Uiso 1 1 calc R . . . . C202 C 0.3050(14) 0.7726(8) 0.3834(7) 0.105(3) Uani 1 1 d . U . . . C203 C 0.4418(14) 0.7810(8) 0.3563(8) 0.109(3) Uani 1 1 d . U . . . C204 C 0.4949(12) 0.6755(11) 0.3236(9) 0.117(3) Uani 1 1 d . U . . . H204 H 0.5879 0.6841 0.3049 0.140 Uiso 1 1 calc R . . . . C205 C 0.4032(10) 0.5573(9) 0.3200(8) 0.085(2) Uani 1 1 d . U . . . C206 C 0.2624(8) 0.5449(7) 0.3454(6) 0.0669(18) Uani 1 1 d . U . . . C207 C 0.1561(9) 0.4070(6) 0.4598(6) 0.0645(17) Uani 1 1 d . U . . . H20A H 0.0646 0.3332 0.4419 0.077 Uiso 1 1 calc R . . . . H20B H 0.1426 0.4859 0.5126 0.077 Uiso 1 1 calc R . . . . C208 C 0.2932(9) 0.3846(7) 0.5340(7) 0.0752(19) Uani 1 1 d . U . . . C209 C 0.2780(14) 0.3953(11) 0.6623(8) 0.121(3) Uani 1 1 d . U . . . H20C H 0.2606 0.4764 0.7013 0.182 Uiso 1 1 calc GR . . . . H20D H 0.3703 0.3941 0.7131 0.182 Uiso 1 1 calc GR . . . . H20E H 0.1931 0.3223 0.6550 0.182 Uiso 1 1 calc GR . . . . C210 C 0.3204(12) 0.2610(9) 0.4660(9) 0.105(3) Uani 1 1 d . U . . . H21D H 0.2326 0.1863 0.4501 0.158 Uiso 1 1 calc GR . . . . H21E H 0.4090 0.2545 0.5169 0.158 Uiso 1 1 calc GR . . . . H21F H 0.3370 0.2627 0.3872 0.158 Uiso 1 1 calc GR . . . . C211 C 0.0942(7) 0.3211(6) 0.2253(6) 0.0559(15) Uani 1 1 d . U . . . C212 C -0.0517(7) 0.1084(6) 0.1122(6) 0.0557(15) Uani 1 1 d . U . . . C213 C -0.0434(8) 0.1236(6) -0.0032(6) 0.0634(17) Uani 1 1 d . U . . . C214 C 0.0971(8) 0.3420(7) 0.1119(6) 0.0696(19) Uani 1 1 d . U . . . H214 H 0.1451 0.4263 0.1148 0.084 Uiso 1 1 calc R . . . . C215 C -0.1324(10) -0.0258(7) 0.2272(8) 0.086(2) Uani 1 1 d . U . . . H21A H -0.1943 -0.1144 0.2111 0.129 Uiso 1 1 calc GR . . . . H21B H -0.1753 0.0352 0.2732 0.129 Uiso 1 1 calc GR . . . . H21C H -0.0301 -0.0089 0.2762 0.129 Uiso 1 1 calc GR . . . . C216 C -0.1061(10) 0.0211(8) -0.1277(7) 0.077(2) Uani 1 1 d . U . . . C217 C -0.0672(10) 0.0535(8) -0.2357(7) 0.082(2) Uani 1 1 d . U . . . H217 H 0.0187 0.1344 -0.2143 0.099 Uiso 1 1 calc R . . . . C218 C -0.1972(10) 0.0188(7) -0.3512(7) 0.088(2) Uani 1 1 d . U . . . H218 H -0.3003 -0.0259 -0.3496 0.106 Uiso 1 1 calc R . . . . C219 C -0.0901(17) -0.0555(11) -0.3541(8) 0.145(4) Uani 1 1 d . U . . . H21G H -0.0176 -0.0419 -0.4021 0.174 Uiso 1 1 calc R . . . . H21H H -0.1274 -0.1449 -0.3561 0.174 Uiso 1 1 calc R . . . . C220 C -0.1842(11) 0.1120(7) -0.4163(6) 0.0823(19) Uani 1 1 d . U . . . 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 0.173(2) 0.0738(13) 0.1104(18) 0.0232(12) 0.0401(17) 0.0458(14) F101 0.125(4) 0.104(3) 0.112(4) 0.046(3) 0.028(3) -0.004(3) F102 0.102(3) 0.104(3) 0.116(4) 0.038(3) 0.053(3) 0.055(3) F103 0.098(4) 0.144(4) 0.117(4) 0.063(4) -0.017(3) 0.000(3) O101 0.092(4) 0.077(3) 0.076(3) 0.043(3) 0.017(3) 0.007(3) O102 0.182(7) 0.071(3) 0.093(4) 0.011(3) 0.056(4) 0.005(4) O103 0.226(8) 0.102(4) 0.131(5) 0.032(4) 0.113(6) 0.039(5) O104 0.236(8) 0.096(4) 0.102(4) 0.044(4) 0.063(5) -0.004(5) N101 0.069(3) 0.072(3) 0.048(3) 0.023(3) 0.021(3) 0.022(3) N102 0.063(3) 0.063(3) 0.051(3) 0.028(3) 0.016(2) 0.021(3) N103 0.075(4) 0.055(3) 0.049(3) 0.021(2) 0.018(3) 0.021(3) C101 0.076(4) 0.070(4) 0.051(4) 0.016(3) 0.015(3) 0.029(3) C102 0.098(5) 0.062(4) 0.052(4) 0.010(3) 0.012(4) 0.019(4) C103 0.085(5) 0.082(5) 0.063(5) 0.023(4) 0.017(4) 0.006(4) C104 0.071(4) 0.107(5) 0.078(5) 0.035(4) 0.032(4) 0.026(4) C105 0.081(5) 0.080(5) 0.069(4) 0.026(4) 0.031(4) 0.031(4) C106 0.060(4) 0.064(4) 0.044(3) 0.012(3) 0.013(3) 0.020(3) C107 0.086(5) 0.095(5) 0.049(4) 0.025(4) 0.026(3) 0.028(4) C108 0.091(5) 0.104(5) 0.054(4) 0.033(4) 0.009(4) 0.020(4) C109 0.190(11) 0.201(11) 0.063(5) 0.067(6) 0.036(6) 0.086(9) C110 0.106(7) 0.128(7) 0.086(6) 0.050(5) 0.014(5) 0.056(6) C111 0.053(4) 0.064(3) 0.051(3) 0.028(3) 0.017(3) 0.027(3) C112 0.061(4) 0.061(4) 0.066(4) 0.034(3) 0.018(3) 0.016(3) C113 0.065(4) 0.055(3) 0.057(3) 0.025(3) 0.023(3) 0.024(3) C114 0.088(5) 0.050(3) 0.049(3) 0.023(3) 0.021(3) 0.017(3) C115 0.122(7) 0.100(6) 0.099(6) 0.068(5) 0.034(5) 0.016(5) C116 0.079(5) 0.058(4) 0.065(4) 0.018(3) 0.019(3) 0.017(3) C117 0.146(7) 0.064(4) 0.060(4) 0.016(3) 0.012(4) 0.024(4) C118 0.126(7) 0.078(5) 0.071(5) 0.015(4) 0.035(4) 0.025(5) C119 0.197(10) 0.242(13) 0.057(5) 0.014(6) 0.011(6) 0.132(10) C120 0.142(7) 0.081(5) 0.070(5) 0.019(4) 0.032(5) 0.013(5) Cl12 0.355(5) 0.0710(14) 0.104(2) 0.0184(14) 0.010(3) 0.087(2) F201 0.241(7) 0.094(4) 0.127(4) 0.050(3) 0.005(5) -0.061(4) F202 0.104(4) 0.125(4) 0.146(5) 0.055(4) 0.061(4) 0.055(3) F203 0.090(3) 0.123(4) 0.138(4) 0.065(3) 0.003(3) 0.010(3) O201 0.087(3) 0.061(3) 0.069(3) 0.024(2) 0.019(3) 0.011(2) O202 0.175(6) 0.071(3) 0.069(3) 0.021(3) 0.003(4) 0.007(4) O203 0.123(4) 0.083(3) 0.076(3) 0.044(3) 0.031(3) 0.026(3) O204 0.121(5) 0.150(6) 0.157(6) 0.094(5) 0.060(4) 0.038(4) N201 0.072(3) 0.050(3) 0.056(3) 0.016(2) 0.020(3) 0.019(2) N202 0.063(3) 0.053(3) 0.058(3) 0.023(2) 0.017(3) 0.022(2) N203 0.092(4) 0.067(3) 0.056(3) 0.028(3) 0.015(3) 0.022(3) C201 0.106(5) 0.054(4) 0.059(4) 0.011(3) 0.004(4) 0.020(4) C202 0.165(7) 0.053(4) 0.061(5) 0.015(4) -0.004(5) 0.010(4) C203 0.147(7) 0.064(5) 0.064(5) 0.026(4) -0.008(5) -0.025(5) C204 0.116(7) 0.105(6) 0.097(7) 0.039(5) 0.020(5) -0.012(5) C205 0.080(5) 0.078(5) 0.089(5) 0.035(4) 0.024(4) 0.009(4) C206 0.078(4) 0.061(4) 0.055(4) 0.025(3) 0.011(3) 0.013(3) C207 0.085(4) 0.055(4) 0.051(3) 0.013(3) 0.026(3) 0.023(3) C208 0.079(5) 0.077(4) 0.069(4) 0.031(4) 0.020(4) 0.021(4) C209 0.170(9) 0.137(8) 0.069(5) 0.045(5) 0.033(5) 0.062(7) C210 0.116(7) 0.112(6) 0.106(6) 0.046(5) 0.027(5) 0.066(5) C211 0.064(4) 0.052(3) 0.051(3) 0.016(3) 0.015(3) 0.021(3) C212 0.056(4) 0.051(3) 0.059(4) 0.018(3) 0.015(3) 0.021(3) C213 0.073(4) 0.062(4) 0.052(3) 0.021(3) 0.013(3) 0.019(3) C214 0.074(5) 0.067(4) 0.060(4) 0.024(3) 0.009(3) 0.016(4) C215 0.099(6) 0.076(5) 0.088(5) 0.042(4) 0.032(4) 0.017(4) C216 0.099(5) 0.070(4) 0.055(4) 0.017(3) 0.008(3) 0.033(4) C217 0.095(5) 0.098(5) 0.052(4) 0.023(4) 0.016(3) 0.038(4) C218 0.118(6) 0.058(4) 0.066(4) 0.023(3) -0.002(4) 0.011(4) C219 0.264(13) 0.137(8) 0.066(5) 0.037(5) 0.046(6) 0.121(9) C220 0.106(6) 0.063(4) 0.057(4) 0.016(3) 0.012(4) 0.008(4) 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 117.3(6) . . ? C120 O103 H103 109.5 . . ? C106 N101 C107 117.9(6) . . ? C111 N101 C106 120.2(5) . . ? C111 N101 C107 121.8(5) . . ? C112 N102 C111 118.4(5) . . ? C114 N103 C113 119.6(5) . . ? C102 C101 H101 120.0 . . ? C106 C101 H101 120.0 . . ? C106 C101 C102 120.0(7) . . ? C101 C102 Cl11 120.0(7) . . ? C103 C102 Cl11 121.8(6) . . ? C103 C102 C101 118.2(7) . . ? F101 C103 C102 116.7(8) . . ? C104 C103 F101 121.2(8) . . ? C104 C103 C102 122.1(7) . . ? C103 C104 H104 120.5 . . ? C103 C104 C105 118.9(8) . . ? C105 C104 H104 120.5 . . ? F102 C105 C104 117.6(7) . . ? F102 C105 C106 119.1(6) . . ? C106 C105 C104 123.3(8) . . ? C101 C106 N101 120.9(6) . . ? C105 C106 N101 121.6(6) . . ? C105 C106 C101 117.4(6) . . ? N101 C107 H10A 108.5 . . ? N101 C107 H10B 108.5 . . ? N101 C107 C108 115.0(6) . . ? H10A C107 H10B 107.5 . . ? C108 C107 H10A 108.5 . . ? C108 C107 H10B 108.5 . . ? F103 C108 C107 105.1(6) . . ? F103 C108 C109 107.4(7) . . ? F103 C108 C110 107.0(8) . . ? C109 C108 C107 110.2(8) . . ? C110 C108 C107 114.5(7) . . ? C110 C108 C109 112.1(8) . . ? 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 122.5(6) . . ? N102 C111 N101 118.2(5) . . ? N102 C111 C114 119.3(6) . . ? O101 C112 C113 118.1(6) . . ? N102 C112 O101 118.8(5) . . ? N102 C112 C113 123.0(5) . . ? N103 C113 C112 117.9(6) . . ? N103 C113 C116 116.9(5) . . ? C112 C113 C116 125.2(5) . . ? N103 C114 C111 121.8(5) . . ? N103 C114 H114 119.1 . . ? C111 C114 H114 119.1 . . ? 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 122.1(6) . . ? O102 C116 C117 119.0(7) . . ? C117 C116 C113 118.9(6) . . ? C116 C117 H117 115.7 . . ? C116 C117 C118 120.4(7) . . ? C118 C117 H117 115.7 . . ? C119 C117 C116 119.4(9) . . ? C119 C117 H117 115.7 . . ? C119 C117 C118 57.5(6) . . ? C117 C118 H118 116.4 . . ? C119 C118 C117 59.8(6) . . ? C119 C118 H118 116.4 . . ? C119 C118 C120 116.4(10) . . ? C120 C118 C117 119.6(7) . . ? C120 C118 H118 116.4 . . ? C117 C119 H11G 117.5 . . ? C117 C119 H11H 117.5 . . ? C118 C119 C117 62.7(7) . . ? C118 C119 H11G 117.5 . . ? C118 C119 H11H 117.5 . . ? H11G C119 H11H 114.6 . . ? O103 C120 C118 116.8(7) . . ? O104 C120 O103 118.4(8) . . ? O104 C120 C118 124.7(9) . . ? C212 O201 C215 118.5(5) . . ? C220 O203 H203 109.5 . . ? C206 N201 C207 118.2(5) . . ? C211 N201 C206 119.4(5) . . ? C211 N201 C207 122.3(5) . . ? C212 N202 C211 117.8(5) . . ? C214 N203 C213 120.0(5) . . ? C202 C201 H201 120.0 . . ? C202 C201 C206 120.1(9) . . ? C206 C201 H201 120.0 . . ? C201 C202 Cl12 121.6(10) . . ? C201 C202 C203 118.7(10) . . ? C203 C202 Cl12 119.8(8) . . ? F201 C203 C204 114.9(12) . . ? C202 C203 F201 121.4(11) . . ? C202 C203 C204 123.7(8) . . ? C203 C204 H204 121.7 . . ? C205 C204 C203 116.5(10) . . ? C205 C204 H204 121.7 . . ? F202 C205 C204 119.4(9) . . ? F202 C205 C206 119.3(7) . . ? C204 C205 C206 121.2(9) . . ? C201 C206 N201 120.6(7) . . ? C201 C206 C205 119.8(7) . . ? C205 C206 N201 119.6(7) . . ? N201 C207 H20A 108.7 . . ? N201 C207 H20B 108.7 . . ? N201 C207 C208 114.3(6) . . ? H20A C207 H20B 107.6 . . ? C208 C207 H20A 108.7 . . ? C208 C207 H20B 108.7 . . ? F203 C208 C207 106.2(5) . . ? F203 C208 C209 107.2(7) . . ? F203 C208 C210 106.4(7) . . ? C209 C208 C207 109.3(7) . . ? C210 C208 C207 114.0(6) . . ? C210 C208 C209 113.2(7) . . ? 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 H21D 109.5 . . ? C208 C210 H21E 109.5 . . ? C208 C210 H21F 109.5 . . ? H21D C210 H21E 109.5 . . ? H21D C210 H21F 109.5 . . ? H21E C210 H21F 109.5 . . ? N201 C211 C214 121.1(6) . . ? N202 C211 N201 118.8(5) . . ? N202 C211 C214 120.2(6) . . ? O201 C212 C213 118.8(6) . . ? N202 C212 O201 117.7(6) . . ? N202 C212 C213 123.5(5) . . ? N203 C213 C212 117.1(6) . . ? N203 C213 C216 116.3(6) . . ? C212 C213 C216 126.5(6) . . ? N203 C214 C211 121.2(6) . . ? N203 C214 H214 119.4 . . ? C211 C214 H214 119.4 . . ? O201 C215 H21A 109.5 . . ? O201 C215 H21B 109.5 . . ? O201 C215 H21C 109.5 . . ? H21A C215 H21B 109.5 . . ? H21A C215 H21C 109.5 . . ? H21B C215 H21C 109.5 . . ? O202 C216 C213 122.0(7) . . ? O202 C216 C217 119.8(7) . . ? C213 C216 C217 118.1(6) . . ? C216 C217 H217 116.4 . . ? C216 C217 C218 117.6(7) . . ? C218 C217 H217 116.4 . . ? C219 C217 C216 118.8(8) . . ? C219 C217 H217 116.4 . . ? C219 C217 C218 58.9(6) . . ? C217 C218 H218 116.8 . . ? C219 C218 C217 59.5(6) . . ? C219 C218 H218 116.8 . . ? C220 C218 C217 116.4(7) . . ? C220 C218 H218 116.8 . . ? C220 C218 C219 118.1(9) . . ? C217 C219 H21G 117.6 . . ? C217 C219 H21H 117.6 . . ? C218 C219 C217 61.6(6) . . ? C218 C219 H21G 117.6 . . ? C218 C219 H21H 117.6 . . ? H21G C219 H21H 114.7 . . ? O203 C220 C218 112.1(8) . . ? O204 C220 O203 122.3(7) . . ? O204 C220 C218 125.5(9) . . ? 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 1.715(8) . ? F101 C103 1.351(8) . ? F102 C105 1.340(8) . ? F103 C108 1.409(9) . ? O101 C112 1.346(8) . ? O101 C115 1.458(9) . ? O102 C116 1.210(9) . ? O103 H103 0.8200 . ? O103 C120 1.332(10) . ? O104 C120 1.209(9) . ? N101 C106 1.434(8) . ? N101 C107 1.468(8) . ? N101 C111 1.355(8) . ? N102 C111 1.320(8) . ? N102 C112 1.319(8) . ? N103 C113 1.334(7) . ? N103 C114 1.309(8) . ? C101 H101 0.9300 . ? C101 C102 1.395(10) . ? C101 C106 1.393(9) . ? C102 C103 1.370(11) . ? C103 C104 1.330(11) . ? C104 H104 0.9300 . ? C104 C105 1.355(11) . ? C105 C106 1.351(9) . ? C107 H10A 0.9700 . ? C107 H10B 0.9700 . ? C107 C108 1.521(11) . ? C108 C109 1.507(11) . ? C108 C110 1.492(12) . ? 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 1.408(8) . ? C112 C113 1.399(9) . ? C113 C116 1.485(10) . ? C114 H114 0.9300 . ? C115 H11D 0.9600 . ? C115 H11E 0.9600 . ? C115 H11F 0.9600 . ? C116 C117 1.471(11) . ? C117 H117 0.9800 . ? C117 C118 1.497(11) . ? C117 C119 1.455(14) . ? C118 H118 0.9800 . ? C118 C119 1.421(14) . ? C118 C120 1.463(11) . ? C119 H11G 0.9700 . ? C119 H11H 0.9700 . ? Cl12 C202 1.703(11) . ? F201 C203 1.378(9) . ? F202 C205 1.329(10) . ? F203 C208 1.424(8) . ? O201 C212 1.333(7) . ? O201 C215 1.431(9) . ? O202 C216 1.220(9) . ? O203 H203 0.8200 . ? O203 C220 1.311(10) . ? O204 C220 1.195(9) . ? N201 C206 1.419(8) . ? N201 C207 1.465(8) . ? N201 C211 1.376(8) . ? N202 C211 1.332(7) . ? N202 C212 1.307(8) . ? N203 C213 1.353(8) . ? N203 C214 1.302(8) . ? C201 H201 0.9300 . ? C201 C202 1.367(11) . ? C201 C206 1.380(10) . ? C202 C203 1.370(15) . ? C203 C204 1.382(15) . ? C204 H204 0.9300 . ? C204 C205 1.374(12) . ? C205 C206 1.394(11) . ? C207 H20A 0.9700 . ? C207 H20B 0.9700 . ? C207 C208 1.532(10) . ? C208 C209 1.492(11) . ? C208 C210 1.491(11) . ? C209 H20C 0.9600 . ? C209 H20D 0.9600 . ? C209 H20E 0.9600 . ? C210 H21D 0.9600 . ? C210 H21E 0.9600 . ? C210 H21F 0.9600 . ? C211 C214 1.407(9) . ? C212 C213 1.411(9) . ? C213 C216 1.446(10) . ? C214 H214 0.9300 . ? C215 H21A 0.9600 . ? C215 H21B 0.9600 . ? C215 H21C 0.9600 . ? C216 C217 1.488(10) . ? C217 H217 0.9800 . ? C217 C218 1.506(11) . ? C217 C219 1.475(12) . ? C218 H218 0.9800 . ? C218 C219 1.465(14) . ? C218 C220 1.460(10) . ? 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 O103 H103 O202 0.82 2.02 2.686(9) 138.0 1_666 O203 H203 N103 0.82 2.01 2.803(7) 162.7 1_454 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 -1.1(9) . . . . ? Cl11 C102 C103 C104 178.5(6) . . . . ? F101 C103 C104 C105 178.0(7) . . . . ? F102 C105 C106 N101 -1.8(10) . . . . ? F102 C105 C106 C101 179.4(6) . . . . ? O101 C112 C113 N103 179.6(6) . . . . ? O101 C112 C113 C116 -0.6(10) . . . . ? O102 C116 C117 C118 20.7(14) . . . . ? O102 C116 C117 C119 -46.7(13) . . . . ? N101 C107 C108 F103 -58.4(9) . . . . ? N101 C107 C108 C109 -173.9(8) . . . . ? N101 C107 C108 C110 58.6(9) . . . . ? N101 C111 C114 N103 -179.7(6) . . . . ? N102 C111 C114 N103 0.3(10) . . . . ? N102 C112 C113 N103 0.6(10) . . . . ? N102 C112 C113 C116 -179.5(7) . . . . ? N103 C113 C116 O102 174.2(8) . . . . ? N103 C113 C116 C117 -5.4(10) . . . . ? C101 C102 C103 F101 -179.8(6) . . . . ? C101 C102 C103 C104 -0.1(11) . . . . ? C102 C101 C106 N101 -178.5(6) . . . . ? C102 C101 C106 C105 0.2(9) . . . . ? C102 C103 C104 C105 -1.7(12) . . . . ? C103 C104 C105 F102 -178.6(7) . . . . ? C103 C104 C105 C106 2.9(13) . . . . ? C104 C105 C106 N101 176.6(7) . . . . ? C104 C105 C106 C101 -2.1(11) . . . . ? C106 N101 C107 C108 77.3(8) . . . . ? C106 N101 C111 N102 -168.2(6) . . . . ? C106 N101 C111 C114 11.8(9) . . . . ? C106 C101 C102 Cl11 -177.8(5) . . . . ? C106 C101 C102 C103 0.9(10) . . . . ? C107 N101 C106 C101 68.8(8) . . . . ? C107 N101 C106 C105 -109.9(8) . . . . ? C107 N101 C111 N102 8.6(9) . . . . ? C107 N101 C111 C114 -171.3(7) . . . . ? C111 N101 C106 C101 -114.2(7) . . . . ? C111 N101 C106 C105 67.1(9) . . . . ? C111 N101 C107 C108 -99.6(8) . . . . ? C111 N102 C112 O101 -177.9(6) . . . . ? C111 N102 C112 C113 1.1(10) . . . . ? C112 N102 C111 N101 178.6(6) . . . . ? C112 N102 C111 C114 -1.5(9) . . . . ? C112 C113 C116 O102 -5.7(12) . . . . ? C112 C113 C116 C117 174.7(7) . . . . ? C113 N103 C114 C111 1.4(10) . . . . ? C113 C116 C117 C118 -159.7(8) . . . . ? C113 C116 C117 C119 132.9(9) . . . . ? C114 N103 C113 C112 -1.8(9) . . . . ? C114 N103 C113 C116 178.3(6) . . . . ? C115 O101 C112 N102 3.0(10) . . . . ? C115 O101 C112 C113 -176.0(7) . . . . ? C116 C117 C118 C119 -107.6(12) . . . . ? C116 C117 C118 C120 147.3(9) . . . . ? C116 C117 C119 C118 109.3(8) . . . . ? C117 C118 C120 O103 -153.8(10) . . . . ? C117 C118 C120 O104 26.8(15) . . . . ? C119 C117 C118 C120 -105.2(12) . . . . ? C119 C118 C120 O103 137.6(11) . . . . ? C119 C118 C120 O104 -41.8(14) . . . . ? C120 C118 C119 C117 110.4(8) . . . . ? Cl12 C202 C203 F201 1.4(11) . . . . ? Cl12 C202 C203 C204 -178.3(7) . . . . ? F201 C203 C204 C205 179.7(8) . . . . ? F202 C205 C206 N201 3.8(11) . . . . ? F202 C205 C206 C201 -178.2(7) . . . . ? O201 C212 C213 N203 179.1(6) . . . . ? O201 C212 C213 C216 -2.5(11) . . . . ? O202 C216 C217 C218 47.7(11) . . . . ? O202 C216 C217 C219 -20.0(13) . . . . ? N201 C207 C208 F203 54.8(7) . . . . ? N201 C207 C208 C209 170.1(7) . . . . ? N201 C207 C208 C210 -62.0(8) . . . . ? N201 C211 C214 N203 175.1(6) . . . . ? N202 C211 C214 N203 -5.9(11) . . . . ? N202 C212 C213 N203 -2.2(10) . . . . ? N202 C212 C213 C216 176.2(7) . . . . ? N203 C213 C216 O202 -171.3(8) . . . . ? N203 C213 C216 C217 6.4(10) . . . . ? C201 C202 C203 F201 -179.9(7) . . . . ? C201 C202 C203 C204 0.4(13) . . . . ? C202 C201 C206 N201 179.8(7) . . . . ? C202 C201 C206 C205 1.9(11) . . . . ? C202 C203 C204 C205 -0.6(14) . . . . ? C203 C204 C205 F202 177.6(8) . . . . ? C203 C204 C205 C206 1.4(13) . . . . ? C204 C205 C206 N201 180.0(8) . . . . ? C204 C205 C206 C201 -2.1(12) . . . . ? C206 N201 C207 C208 -79.4(8) . . . . ? C206 N201 C211 N202 176.9(6) . . . . ? C206 N201 C211 C214 -4.2(10) . . . . ? C206 C201 C202 Cl12 177.7(6) . . . . ? C206 C201 C202 C203 -1.0(12) . . . . ? C207 N201 C206 C201 -69.2(9) . . . . ? C207 N201 C206 C205 108.7(8) . . . . ? C207 N201 C211 N202 -5.9(9) . . . . ? C207 N201 C211 C214 173.0(7) . . . . ? C211 N201 C206 C201 108.1(8) . . . . ? C211 N201 C206 C205 -74.0(9) . . . . ? C211 N201 C207 C208 103.4(7) . . . . ? C211 N202 C212 O201 178.6(6) . . . . ? C211 N202 C212 C213 -0.1(9) . . . . ? C212 N202 C211 N201 -177.0(6) . . . . ? C212 N202 C211 C214 4.0(9) . . . . ? C212 C213 C216 O202 10.3(13) . . . . ? C212 C213 C216 C217 -172.0(7) . . . . ? C213 N203 C214 C211 3.5(11) . . . . ? C213 C216 C217 C218 -130.0(8) . . . . ? C213 C216 C217 C219 162.2(9) . . . . ? C214 N203 C213 C212 0.4(10) . . . . ? C214 N203 C213 C216 -178.2(7) . . . . ? C215 O201 C212 N202 -0.8(9) . . . . ? C215 O201 C212 C213 177.9(7) . . . . ? C216 C217 C218 C219 -108.6(9) . . . . ? C216 C217 C218 C220 142.8(8) . . . . ? C216 C217 C219 C218 106.6(8) . . . . ? C217 C218 C220 O203 -123.7(8) . . . . ? C217 C218 C220 O204 54.1(11) . . . . ? C219 C217 C218 C220 -108.5(10) . . . . ? C219 C218 C220 O203 168.4(8) . . . . ? C219 C218 C220 O204 -13.8(12) . . . . ? C220 C218 C219 C217 105.7(8) . . . . ?