#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:50:34 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205058 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229940.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_7229940 loop_ _publ_author_name 'Nisar, Madiha' 'Sung, Herman H-Y.' 'Puschmann, Horst' 'Lakerveld, Richard' 'Haynes, Richard' 'Williams, Ian Duncan' _publ_section_title ; 11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01875D _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H23 N O4, C7 H6 O2' _chemical_formula_sum 'C22 H29 N O6' _chemical_formula_weight 403.46 _chemical_name_common 11-Aza:Ben _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _audit_creation_date 2017-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-08-15 deposited with the CCDC. 2018-01-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.9437(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.64312(19) _cell_length_b 9.3622(2) _cell_length_c 22.8165(4) _cell_measurement_reflns_used 5119 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 75.3250 _cell_measurement_theta_min 4.5700 _cell_volume 2059.61(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (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_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.997 _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 48.00 106.00 1.00 3.00 -- 110.57-102.00 119.00 58 2 \w 11.00 117.00 1.00 1.00 -- 40.57 77.00-180.00 106 3 \w -67.00 36.00 1.00 1.00 -- -40.57 37.00-120.00 103 4 \w -65.00 36.00 1.00 1.00 -- -40.57 37.00 150.00 101 5 \w 42.00 128.00 1.00 3.00 -- 110.57 -30.00 30.00 86 6 \w 85.00 172.00 1.00 3.00 -- 110.57 41.00 7.00 87 7 \w 80.00 170.00 1.00 3.00 -- 110.57 61.00-150.00 90 8 \w 83.00 178.00 1.00 3.00 -- 110.57 77.00 30.00 95 9 \w 81.00 146.00 1.00 3.00 -- 110.57 77.00 120.00 65 10 \w 73.00 131.00 1.00 3.00 -- 110.57 178.00 -90.00 58 11 \w 26.00 106.00 1.00 3.00 -- 110.57 -94.00 0.00 80 12 \w 35.00 115.00 1.00 3.00 -- 110.57-111.00-120.00 80 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0430966000 _diffrn_orient_matrix_UB_12 0.1554552000 _diffrn_orient_matrix_UB_13 -0.0128475000 _diffrn_orient_matrix_UB_21 -0.1368507000 _diffrn_orient_matrix_UB_22 -0.0242633000 _diffrn_orient_matrix_UB_23 0.0325116000 _diffrn_orient_matrix_UB_31 0.0704463000 _diffrn_orient_matrix_UB_32 0.0481925000 _diffrn_orient_matrix_UB_33 0.0577464000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_unetI/netI 0.0514 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 11649 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.499 _diffrn_reflns_theta_min 3.875 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.776 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93665 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.185 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 2798 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 545 _refine_ls_number_reflns 7317 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0348 _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^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.0818 _reflns_Friedel_coverage 0.851 _reflns_Friedel_fraction_full 0.970 _reflns_Friedel_fraction_max 0.969 _reflns_number_gt 6668 _reflns_number_total 7317 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd2_madiha36cult _cod_original_cell_volume 2059.60(7) _cod_database_code 7229940 _shelx_shelxl_version_number 2014/7 _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. ; _reflns_odcompleteness_completeness 99.73 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _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 2.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C2A(H2A), C6A(H6A), C9A(H9A), C11A(H11C), C12A(H12A) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C4A(H4AA,H4AB), C5A(H5AA, H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB) 2.c Aromatic/amide H refined with riding coordinates: C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13A(H13D,H13E, H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F) ; _shelx_res_file ; madiha36cult.res created by SHELXL-2014/7 TITL madiha36CuLT solution in P21 CELL 1.54184 9.643124 9.362155 22.816468 90 90.9437 90 ZERR 4 0.000186 0.000203 0.000446 0 0.0018 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 88 116 4 24 L.S. 6 PLAN 25 TEMP -173 HTAB N11 O20 HTAB O21 O10 HTAB N11A O20A HTAB O21A O10A CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT -3 0 10 OMIT 2 -1 9 OMIT 2 -5 17 OMIT -8 -1 11 OMIT -1 0 2 OMIT -2 -10 9 OMIT 4 6 11 OMIT -3 3 6 OMIT 2 5 20 OMIT -9 1 11 OMIT 1 1 3 OMIT 3 0 4 OMIT 7 1 11 OMIT 11 -1 4 OMIT 5 -9 11 OMIT 3 1 5 OMIT 0 6 12 REM REM REM WGHT 0.036000 FVAR 5.72625 O1 4 0.450033 0.565866 0.412521 11.00000 0.01751 0.01808 = 0.02911 0.00234 -0.00060 -0.00211 O2 4 0.595955 0.585643 0.430414 11.00000 0.01613 0.02216 = 0.02991 -0.00559 0.00216 -0.00347 O3 4 0.645149 0.346188 0.441465 11.00000 0.01576 0.02445 = 0.02144 -0.00174 0.00343 0.00358 O10 4 0.404342 0.483651 0.600873 11.00000 0.02370 0.02493 = 0.01814 -0.00161 0.00183 0.00221 N11 3 0.503714 0.389954 0.521442 11.00000 0.01630 0.02356 = 0.01824 0.00033 -0.00138 0.00196 H11 2 0.576050 0.365388 0.544963 11.00000 0.02762 C1 1 0.403389 0.419001 0.421452 11.00000 0.01762 0.01540 = 0.02051 0.00101 -0.00011 -0.00051 C2 1 0.506471 0.339237 0.460980 11.00000 0.01656 0.01893 = 0.01984 0.00020 0.00065 0.00058 AFIX 13 H2 2 0.478559 0.236368 0.461143 11.00000 -1.20000 AFIX 0 C3 1 0.673180 0.470730 0.407151 11.00000 0.01943 0.02291 = 0.02566 -0.00402 0.00545 -0.00148 C4 1 0.637625 0.444654 0.342084 11.00000 0.02436 0.03021 = 0.02215 -0.00185 0.00726 -0.00653 AFIX 23 H4A 2 0.601767 0.534563 0.324745 11.00000 -1.20000 H4B 2 0.723737 0.419385 0.321448 11.00000 -1.20000 AFIX 0 C5 1 0.530595 0.326534 0.331548 11.00000 0.02317 0.02691 = 0.01761 -0.00214 0.00195 -0.00316 AFIX 23 H5A 2 0.570103 0.235472 0.346237 11.00000 -1.20000 H5B 2 0.515400 0.316163 0.288741 11.00000 -1.20000 AFIX 0 C6 1 0.306100 0.208191 0.361853 11.00000 0.01922 0.01959 = 0.02295 0.00008 -0.00289 -0.00101 AFIX 13 H6 2 0.363987 0.135507 0.383065 11.00000 -1.20000 AFIX 0 C7 1 0.169970 0.224592 0.394484 11.00000 0.01993 0.02725 = 0.02818 -0.00006 -0.00032 -0.00465 AFIX 23 H7A 2 0.106497 0.286524 0.371296 11.00000 -1.20000 H7B 2 0.125599 0.129724 0.398151 11.00000 -1.20000 AFIX 0 C8 1 0.190759 0.288876 0.455482 11.00000 0.01831 0.02459 = 0.02435 0.00202 0.00279 -0.00163 AFIX 23 H8A 2 0.247900 0.223544 0.479983 11.00000 -1.20000 H8B 2 0.099698 0.300303 0.474340 11.00000 -1.20000 AFIX 0 C9 1 0.280749 0.514540 0.510038 11.00000 0.01590 0.02063 = 0.02555 0.00012 0.00065 0.00166 AFIX 13 H9 2 0.305967 0.614909 0.499668 11.00000 -1.20000 AFIX 0 C10 1 0.399746 0.458484 0.547071 11.00000 0.01774 0.01701 = 0.02181 0.00182 0.00168 -0.00234 C11 1 0.388683 0.349294 0.360246 11.00000 0.01959 0.02117 = 0.01714 0.00158 -0.00017 -0.00048 AFIX 13 H11A 2 0.335004 0.417197 0.334771 11.00000 -1.20000 AFIX 0 C12 1 0.262911 0.435033 0.451507 11.00000 0.01716 0.02113 = 0.01848 0.00204 0.00101 0.00056 AFIX 13 H12 2 0.203542 0.496510 0.425497 11.00000 -1.20000 AFIX 0 C13 1 0.823211 0.510285 0.418663 11.00000 0.02239 0.03772 = 0.03566 -0.01104 0.00689 -0.00367 AFIX 137 H13A 2 0.836531 0.534032 0.460207 11.00000 -1.50000 H13B 2 0.847518 0.593042 0.394620 11.00000 -1.50000 H13C 2 0.882815 0.429415 0.408623 11.00000 -1.50000 AFIX 0 C14 1 0.276589 0.152444 0.299623 11.00000 0.02908 0.02848 = 0.02537 -0.00234 -0.00272 -0.00224 AFIX 137 H14A 2 0.227930 0.226117 0.276742 11.00000 -1.50000 H14B 2 0.218672 0.066620 0.301600 11.00000 -1.50000 H14C 2 0.364324 0.129005 0.280798 11.00000 -1.50000 AFIX 0 C15 1 0.147835 0.525031 0.545454 11.00000 0.01906 0.04440 = 0.02796 -0.00757 0.00253 0.00423 AFIX 137 H15A 2 0.124042 0.430499 0.560754 11.00000 -1.50000 H15B 2 0.072023 0.559814 0.520132 11.00000 -1.50000 H15C 2 0.162281 0.591502 0.578169 11.00000 -1.50000 AFIX 0 O20 4 0.726038 0.333370 0.609237 11.00000 0.02146 0.03040 = 0.02468 -0.00058 0.00125 -0.00067 O21 4 0.552744 0.337088 0.673735 11.00000 0.02140 0.03019 = 0.02350 0.00179 0.00209 0.00762 H21 2 0.510352 0.390867 0.647816 11.00000 0.04639 C20 1 0.676020 0.296045 0.655564 11.00000 0.01842 0.02277 = 0.02375 -0.00430 -0.00283 0.00022 C21 1 0.748058 0.198353 0.697802 11.00000 0.01915 0.02326 = 0.02344 -0.00708 -0.00324 -0.00118 C22 1 0.878109 0.144818 0.683867 11.00000 0.02042 0.02948 = 0.02386 -0.00751 -0.00133 -0.00048 AFIX 43 H22 2 0.921668 0.174259 0.648831 11.00000 -1.20000 AFIX 0 C23 1 0.943794 0.048874 0.721003 11.00000 0.02380 0.03449 = 0.02996 -0.01168 -0.00560 0.00755 AFIX 43 H23 2 1.032401 0.012282 0.711318 11.00000 -1.20000 AFIX 0 C24 1 0.881055 0.005541 0.772450 11.00000 0.03034 0.03174 = 0.03172 -0.00221 -0.00909 0.00907 AFIX 43 H24 2 0.926327 -0.060936 0.797737 11.00000 -1.20000 AFIX 0 C25 1 0.751863 0.059842 0.786744 11.00000 0.02956 0.03739 = 0.02638 0.00209 -0.00246 0.00194 AFIX 43 H25 2 0.708784 0.030605 0.821916 11.00000 -1.20000 AFIX 0 C26 1 0.685639 0.156716 0.749730 11.00000 0.02209 0.02873 = 0.02578 -0.00179 -0.00297 0.00446 AFIX 43 H26 2 0.597801 0.194622 0.759789 11.00000 -1.20000 AFIX 0 O1A 4 0.340359 0.367623 -0.063869 11.00000 0.02071 0.01782 = 0.01589 -0.00075 0.00313 -0.00384 O2A 4 0.298295 0.343625 -0.002983 11.00000 0.01792 0.02022 = 0.01891 0.00072 0.00486 -0.00119 O3A 4 0.300158 0.580374 0.023975 11.00000 0.01320 0.02243 = 0.02026 -0.00497 0.00335 -0.00126 O10A 4 0.757049 0.456582 0.018279 11.00000 0.01545 0.02458 = 0.02217 0.00006 -0.00044 0.00163 N11A 3 0.538319 0.540784 0.014959 11.00000 0.01506 0.02233 = 0.01555 -0.00271 -0.00026 -0.00208 H11B 2 0.554555 0.569903 0.051443 11.00000 0.02959 C1A 1 0.386170 0.513667 -0.073738 11.00000 0.01527 0.01541 = 0.01934 0.00043 0.00108 -0.00304 C2A 1 0.412201 0.590302 -0.015199 11.00000 0.01200 0.01847 = 0.01900 -0.00196 0.00137 -0.00126 AFIX 13 H2A 2 0.425542 0.693892 -0.024183 11.00000 -1.20000 AFIX 0 C3A 1 0.212178 0.458778 0.013203 11.00000 0.01431 0.02089 = 0.02329 -0.00283 0.00348 -0.00108 C4A 1 0.100971 0.492509 -0.033689 11.00000 0.01220 0.03257 = 0.02290 -0.00398 0.00181 -0.00153 AFIX 23 H4AA 2 0.082303 0.404868 -0.056780 11.00000 -1.20000 H4AB 2 0.014093 0.518843 -0.013847 11.00000 -1.20000 AFIX 0 C5A 1 0.139169 0.612321 -0.075670 11.00000 0.01772 0.02613 = 0.02368 -0.00196 -0.00378 0.00414 AFIX 23 H5AA 2 0.149582 0.701719 -0.052844 11.00000 -1.20000 H5AB 2 0.061084 0.626200 -0.103807 11.00000 -1.20000 AFIX 0 C6A 1 0.322648 0.729518 -0.138388 11.00000 0.02493 0.01942 = 0.02181 -0.00042 -0.00381 0.00116 AFIX 13 H6A 2 0.336063 0.801122 -0.106271 11.00000 -1.20000 AFIX 0 C7A 1 0.461031 0.710871 -0.169168 11.00000 0.02899 0.02087 = 0.02076 0.00426 0.00017 -0.00348 AFIX 23 H7AA 2 0.446645 0.650888 -0.204481 11.00000 -1.20000 H7AB 2 0.494554 0.805497 -0.182142 11.00000 -1.20000 AFIX 0 C8A 1 0.571254 0.641983 -0.129764 11.00000 0.02088 0.02287 = 0.02127 0.00219 0.00297 -0.00339 AFIX 23 H8AA 2 0.591763 0.705260 -0.095955 11.00000 -1.20000 H8AB 2 0.657777 0.629278 -0.151936 11.00000 -1.20000 AFIX 0 C9A 1 0.627566 0.413842 -0.070811 11.00000 0.01589 0.01889 = 0.01883 -0.00170 0.00226 -0.00061 AFIX 13 H9A 2 0.587593 0.316188 -0.065617 11.00000 -1.20000 AFIX 0 C10A 1 0.646500 0.475130 -0.009364 11.00000 0.01246 0.01660 = 0.01959 0.00210 0.00287 -0.00268 C11A 1 0.272606 0.588821 -0.110691 11.00000 0.01745 0.02051 = 0.01878 -0.00220 -0.00162 0.00084 AFIX 13 H11C 2 0.247979 0.522985 -0.143769 11.00000 -1.20000 AFIX 0 C12A 1 0.521298 0.497259 -0.107743 11.00000 0.01502 0.01983 = 0.01566 -0.00291 0.00101 -0.00071 AFIX 13 H12A 2 0.499222 0.437861 -0.143108 11.00000 -1.20000 AFIX 0 C13A 1 0.151333 0.414984 0.071119 11.00000 0.01732 0.02943 = 0.02631 -0.00024 0.00499 -0.00076 AFIX 137 H13D 2 0.225711 0.381803 0.097551 11.00000 -1.50000 H13E 2 0.084250 0.337717 0.064649 11.00000 -1.50000 H13F 2 0.104583 0.497033 0.088713 11.00000 -1.50000 AFIX 0 C14A 1 0.213832 0.788541 -0.181726 11.00000 0.03473 0.02605 = 0.02967 0.00317 -0.00770 0.00434 AFIX 137 H14D 2 0.193035 0.716527 -0.211777 11.00000 -1.50000 H14E 2 0.249921 0.874860 -0.200389 11.00000 -1.50000 H14F 2 0.128977 0.811969 -0.160715 11.00000 -1.50000 AFIX 0 C15A 1 0.766502 0.392460 -0.100413 11.00000 0.01572 0.03313 = 0.02119 -0.00324 0.00425 0.00295 AFIX 137 H15D 2 0.815463 0.484017 -0.102389 11.00000 -1.50000 H15E 2 0.750836 0.355494 -0.140157 11.00000 -1.50000 H15F 2 0.822578 0.324113 -0.077733 11.00000 -1.50000 AFIX 0 O20A 4 0.629040 0.613092 0.142941 11.00000 0.01718 0.02743 = 0.02716 0.00381 0.00205 -0.00447 O21A 4 0.843932 0.609740 0.106331 11.00000 0.01692 0.02582 = 0.02437 -0.00326 0.00037 0.00132 H21A 2 0.796143 0.561607 0.077698 11.00000 0.05350 C20A 1 0.749680 0.651128 0.144444 11.00000 0.01775 0.01963 = 0.02209 0.00732 0.00091 0.00279 C21A 1 0.808412 0.750593 0.189921 11.00000 0.01940 0.02097 = 0.01783 0.00428 -0.00015 0.00127 C22A 1 0.728569 0.787480 0.237797 11.00000 0.01768 0.03688 = 0.02677 0.00072 0.00466 -0.00367 AFIX 43 H22A 2 0.638780 0.747413 0.242033 11.00000 -1.20000 AFIX 0 C23A 1 0.779970 0.882960 0.279497 11.00000 0.02569 0.04991 = 0.02524 -0.00774 0.00774 0.00174 AFIX 43 H23A 2 0.725959 0.906917 0.312528 11.00000 -1.20000 AFIX 0 C24A 1 0.910437 0.943282 0.272789 11.00000 0.02612 0.03862 = 0.02558 -0.00739 0.00030 -0.00046 AFIX 43 H24A 2 0.945188 1.009359 0.301010 11.00000 -1.20000 AFIX 0 C25A 1 0.989790 0.907109 0.224986 11.00000 0.01848 0.02760 = 0.02426 0.00080 -0.00007 -0.00295 AFIX 43 H25A 2 1.078653 0.948977 0.220281 11.00000 -1.20000 AFIX 0 C26A 1 0.939809 0.810016 0.184040 11.00000 0.01700 0.02473 = 0.01814 0.00416 0.00158 0.00174 AFIX 43 H26A 2 0.995421 0.783813 0.151782 11.00000 -1.20000 AFIX 0 HKLF 4 REM madiha36CuLT solution in P21 REM R1 = 0.0348 for 6668 Fo > 4sig(Fo) and 0.0403 for all 7317 data REM 545 parameters refined using 1 restraints END WGHT 0.0327 0.0000 REM Highest difference peak 0.185, deepest hole -0.176, 1-sigma level 0.035 Q1 1 0.6390 0.4600 -0.0457 11.00000 0.05 0.19 Q2 1 0.4627 0.5081 -0.0893 11.00000 0.05 0.17 Q3 1 0.5768 0.4640 -0.0877 11.00000 0.05 0.16 Q4 1 0.3474 0.2807 0.3635 11.00000 0.05 0.15 Q5 1 0.4525 0.3875 0.4415 11.00000 0.05 0.15 Q6 1 0.6487 0.4603 0.3730 11.00000 0.05 0.15 Q7 1 0.3356 0.4216 0.4345 11.00000 0.05 0.14 Q8 1 0.3973 0.3694 0.3945 11.00000 0.05 0.14 Q9 1 0.2729 0.4508 0.4876 11.00000 0.05 0.14 Q10 1 0.3813 0.7231 -0.1576 11.00000 0.05 0.13 Q11 1 0.8868 0.2023 0.6235 11.00000 0.05 0.13 Q12 1 0.2372 0.2196 0.3779 11.00000 0.05 0.13 Q13 1 0.3327 0.5578 -0.0930 11.00000 0.05 0.13 Q14 1 0.2801 0.1080 0.4701 11.00000 0.05 0.13 Q15 1 0.4661 0.4454 0.6168 11.00000 0.05 0.13 Q16 1 0.2962 0.6635 -0.1251 11.00000 0.05 0.13 Q17 1 0.8962 0.3327 0.4392 11.00000 0.05 0.12 Q18 1 0.6605 0.6702 0.2540 11.00000 0.05 0.12 Q19 1 0.7594 0.3441 0.0438 11.00000 0.05 0.12 Q20 1 0.4835 0.5698 -0.0026 11.00000 0.05 0.12 Q21 1 0.9750 -0.1575 0.8129 11.00000 0.05 0.12 Q22 1 0.3977 0.5552 -0.0454 11.00000 0.05 0.12 Q23 1 0.8815 0.7158 0.1971 11.00000 0.05 0.11 Q24 1 0.5906 0.5545 -0.0036 11.00000 0.05 0.11 Q25 1 0.3363 0.4815 0.5272 11.00000 0.05 0.11 ; _shelx_res_checksum 64100 _olex2_date_sample_data_collection 2017-06-26 _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 1.176 _oxdiff_exptl_absorpt_empirical_full_min 0.888 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 O1 O 0.4500(2) 0.5659(2) 0.41252(8) 0.0216(4) Uani 1 1 d . O2 O 0.59596(19) 0.5856(2) 0.43041(8) 0.0227(4) Uani 1 1 d . O3 O 0.64515(19) 0.3462(2) 0.44147(8) 0.0205(4) Uani 1 1 d . O10 O 0.4043(2) 0.4837(2) 0.60087(8) 0.0222(4) Uani 1 1 d . N11 N 0.5037(2) 0.3900(2) 0.52144(9) 0.0194(5) Uani 1 1 d . H11 H 0.576(4) 0.365(4) 0.5450(15) 0.028(9) Uiso 1 1 d . C1 C 0.4034(3) 0.4190(3) 0.42145(11) 0.0178(5) Uani 1 1 d . C2 C 0.5065(3) 0.3392(3) 0.46098(11) 0.0184(5) Uani 1 1 d . H2 H 0.4786 0.2364 0.4611 0.022 Uiso 1 1 calc R C3 C 0.6732(3) 0.4707(3) 0.40715(12) 0.0226(6) Uani 1 1 d . C4 C 0.6376(3) 0.4447(3) 0.34208(12) 0.0255(6) Uani 1 1 d . H4A H 0.6018 0.5346 0.3247 0.031 Uiso 1 1 calc R H4B H 0.7237 0.4194 0.3214 0.031 Uiso 1 1 calc R C5 C 0.5306(3) 0.3265(3) 0.33155(11) 0.0225(6) Uani 1 1 d . H5A H 0.5701 0.2355 0.3462 0.027 Uiso 1 1 calc R H5B H 0.5154 0.3162 0.2887 0.027 Uiso 1 1 calc R C6 C 0.3061(3) 0.2082(3) 0.36185(12) 0.0206(5) Uani 1 1 d . H6 H 0.3640 0.1355 0.3831 0.025 Uiso 1 1 calc R C7 C 0.1700(3) 0.2246(3) 0.39448(13) 0.0251(6) Uani 1 1 d . H7A H 0.1065 0.2865 0.3713 0.030 Uiso 1 1 calc R H7B H 0.1256 0.1297 0.3982 0.030 Uiso 1 1 calc R C8 C 0.1908(3) 0.2889(3) 0.45548(12) 0.0224(6) Uani 1 1 d . H8A H 0.2479 0.2235 0.4800 0.027 Uiso 1 1 calc R H8B H 0.0997 0.3003 0.4743 0.027 Uiso 1 1 calc R C9 C 0.2807(3) 0.5145(3) 0.51004(12) 0.0207(5) Uani 1 1 d . H9 H 0.3060 0.6149 0.4997 0.025 Uiso 1 1 calc R C10 C 0.3997(3) 0.4585(3) 0.54707(12) 0.0188(5) Uani 1 1 d . C11 C 0.3887(3) 0.3493(3) 0.36025(11) 0.0193(5) Uani 1 1 d . H11A H 0.3350 0.4172 0.3348 0.023 Uiso 1 1 calc R C12 C 0.2629(3) 0.4350(3) 0.45151(11) 0.0189(5) Uani 1 1 d . H12 H 0.2035 0.4965 0.4255 0.023 Uiso 1 1 calc R C13 C 0.8232(3) 0.5103(4) 0.41866(14) 0.0319(7) Uani 1 1 d . H13A H 0.8365 0.5340 0.4602 0.048 Uiso 1 1 calc GR H13B H 0.8475 0.5930 0.3946 0.048 Uiso 1 1 calc GR H13C H 0.8828 0.4294 0.4086 0.048 Uiso 1 1 calc GR C14 C 0.2766(3) 0.1524(3) 0.29962(13) 0.0277(6) Uani 1 1 d . H14A H 0.2279 0.2261 0.2767 0.042 Uiso 1 1 calc GR H14B H 0.2187 0.0666 0.3016 0.042 Uiso 1 1 calc GR H14C H 0.3643 0.1290 0.2808 0.042 Uiso 1 1 calc GR C15 C 0.1478(3) 0.5250(4) 0.54545(13) 0.0305(7) Uani 1 1 d . H15A H 0.1240 0.4305 0.5608 0.046 Uiso 1 1 calc GR H15B H 0.0720 0.5598 0.5201 0.046 Uiso 1 1 calc GR H15C H 0.1623 0.5915 0.5782 0.046 Uiso 1 1 calc GR O20 O 0.7260(2) 0.3334(2) 0.60924(8) 0.0255(4) Uani 1 1 d . O21 O 0.5527(2) 0.3371(2) 0.67374(8) 0.0250(4) Uani 1 1 d . H21 H 0.510(4) 0.391(5) 0.6478(19) 0.046(12) Uiso 1 1 d . C20 C 0.6760(3) 0.2960(3) 0.65556(12) 0.0217(6) Uani 1 1 d . C21 C 0.7481(3) 0.1984(3) 0.69780(12) 0.0220(6) Uani 1 1 d . C22 C 0.8781(3) 0.1448(3) 0.68387(12) 0.0246(6) Uani 1 1 d . H22 H 0.9217 0.1743 0.6488 0.030 Uiso 1 1 calc R C23 C 0.9438(3) 0.0489(3) 0.72100(13) 0.0295(7) Uani 1 1 d . H23 H 1.0324 0.0123 0.7113 0.035 Uiso 1 1 calc R C24 C 0.8811(3) 0.0055(4) 0.77245(14) 0.0314(7) Uani 1 1 d . H24 H 0.9263 -0.0609 0.7977 0.038 Uiso 1 1 calc R C25 C 0.7519(3) 0.0598(4) 0.78674(13) 0.0311(7) Uani 1 1 d . H25 H 0.7088 0.0306 0.8219 0.037 Uiso 1 1 calc R C26 C 0.6856(3) 0.1567(3) 0.74973(13) 0.0256(6) Uani 1 1 d . H26 H 0.5978 0.1946 0.7598 0.031 Uiso 1 1 calc R O1A O 0.34036(19) 0.3676(2) -0.06387(8) 0.0181(4) Uani 1 1 d . O2A O 0.29829(19) 0.3436(2) -0.00298(8) 0.0190(4) Uani 1 1 d . O3A O 0.30016(18) 0.5804(2) 0.02397(8) 0.0186(4) Uani 1 1 d . O10A O 0.75705(18) 0.4566(2) 0.01828(8) 0.0207(4) Uani 1 1 d . N11A N 0.5383(2) 0.5408(2) 0.01496(10) 0.0177(5) Uani 1 1 d . H11B H 0.555(4) 0.570(4) 0.0514(16) 0.030(9) Uiso 1 1 d . C1A C 0.3862(3) 0.5137(3) -0.07374(11) 0.0167(5) Uani 1 1 d . C2A C 0.4122(2) 0.5903(3) -0.01520(11) 0.0165(5) Uani 1 1 d . H2A H 0.4255 0.6939 -0.0242 0.020 Uiso 1 1 calc R C3A C 0.2122(3) 0.4588(3) 0.01320(12) 0.0195(5) Uani 1 1 d . C4A C 0.1010(3) 0.4925(3) -0.03369(12) 0.0225(6) Uani 1 1 d . H4AA H 0.0823 0.4049 -0.0568 0.027 Uiso 1 1 calc R H4AB H 0.0141 0.5188 -0.0138 0.027 Uiso 1 1 calc R C5A C 0.1392(3) 0.6123(3) -0.07567(12) 0.0226(6) Uani 1 1 d . H5AA H 0.1496 0.7017 -0.0528 0.027 Uiso 1 1 calc R H5AB H 0.0611 0.6262 -0.1038 0.027 Uiso 1 1 calc R C6A C 0.3226(3) 0.7295(3) -0.13839(12) 0.0221(6) Uani 1 1 d . H6A H 0.3361 0.8011 -0.1063 0.027 Uiso 1 1 calc R C7A C 0.4610(3) 0.7109(3) -0.16917(12) 0.0235(6) Uani 1 1 d . H7AA H 0.4466 0.6509 -0.2045 0.028 Uiso 1 1 calc R H7AB H 0.4946 0.8055 -0.1821 0.028 Uiso 1 1 calc R C8A C 0.5713(3) 0.6420(3) -0.12976(12) 0.0216(6) Uani 1 1 d . H8AA H 0.5918 0.7053 -0.0960 0.026 Uiso 1 1 calc R H8AB H 0.6578 0.6293 -0.1519 0.026 Uiso 1 1 calc R C9A C 0.6276(3) 0.4138(3) -0.07081(11) 0.0179(5) Uani 1 1 d . H9A H 0.5876 0.3162 -0.0656 0.021 Uiso 1 1 calc R C10A C 0.6465(3) 0.4751(3) -0.00936(11) 0.0162(5) Uani 1 1 d . C11A C 0.2726(3) 0.5888(3) -0.11069(11) 0.0189(5) Uani 1 1 d . H11C H 0.2480 0.5230 -0.1438 0.023 Uiso 1 1 calc R C12A C 0.5213(3) 0.4973(3) -0.10774(11) 0.0168(5) Uani 1 1 d . H12A H 0.4992 0.4379 -0.1431 0.020 Uiso 1 1 calc R C13A C 0.1513(3) 0.4150(3) 0.07112(12) 0.0243(6) Uani 1 1 d . H13D H 0.2257 0.3818 0.0976 0.036 Uiso 1 1 calc GR H13E H 0.0842 0.3377 0.0646 0.036 Uiso 1 1 calc GR H13F H 0.1046 0.4970 0.0887 0.036 Uiso 1 1 calc GR C14A C 0.2138(3) 0.7885(3) -0.18173(14) 0.0302(7) Uani 1 1 d . H14D H 0.1930 0.7165 -0.2118 0.045 Uiso 1 1 calc GR H14E H 0.2499 0.8749 -0.2004 0.045 Uiso 1 1 calc GR H14F H 0.1290 0.8120 -0.1607 0.045 Uiso 1 1 calc GR C15A C 0.7665(3) 0.3925(3) -0.10041(12) 0.0233(6) Uani 1 1 d . H15D H 0.8155 0.4840 -0.1024 0.035 Uiso 1 1 calc GR H15E H 0.7508 0.3555 -0.1402 0.035 Uiso 1 1 calc GR H15F H 0.8226 0.3241 -0.0777 0.035 Uiso 1 1 calc GR O20A O 0.62904(19) 0.6131(2) 0.14294(8) 0.0239(4) Uani 1 1 d . O21A O 0.84393(19) 0.6097(2) 0.10633(8) 0.0224(4) Uani 1 1 d . H21A H 0.796(5) 0.562(5) 0.078(2) 0.053(13) Uiso 1 1 d . C20A C 0.7497(3) 0.6511(3) 0.14444(12) 0.0198(5) Uani 1 1 d . C21A C 0.8084(3) 0.7506(3) 0.18992(11) 0.0194(5) Uani 1 1 d . C22A C 0.7286(3) 0.7875(4) 0.23780(13) 0.0271(6) Uani 1 1 d . H22A H 0.6388 0.7474 0.2420 0.032 Uiso 1 1 calc R C23A C 0.7800(3) 0.8830(4) 0.27950(13) 0.0335(7) Uani 1 1 d . H23A H 0.7260 0.9069 0.3125 0.040 Uiso 1 1 calc R C24A C 0.9104(3) 0.9433(4) 0.27279(13) 0.0301(7) Uani 1 1 d . H24A H 0.9452 1.0094 0.3010 0.036 Uiso 1 1 calc R C25A C 0.9898(3) 0.9071(3) 0.22499(12) 0.0235(6) Uani 1 1 d . H25A H 1.0787 0.9490 0.2203 0.028 Uiso 1 1 calc R C26A C 0.9398(3) 0.8100(3) 0.18404(11) 0.0199(5) Uani 1 1 d . H26A H 0.9954 0.7838 0.1518 0.024 Uiso 1 1 calc R 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 O1 0.0175(9) 0.0181(9) 0.0291(10) 0.0023(8) -0.0006(7) -0.0021(7) O2 0.0161(9) 0.0222(10) 0.0299(10) -0.0056(8) 0.0022(7) -0.0035(8) O3 0.0158(9) 0.0245(10) 0.0214(9) -0.0017(8) 0.0034(7) 0.0036(8) O10 0.0237(10) 0.0249(10) 0.0181(9) -0.0016(8) 0.0018(7) 0.0022(8) N11 0.0163(11) 0.0236(12) 0.0182(11) 0.0003(9) -0.0014(9) 0.0020(9) C1 0.0176(12) 0.0154(12) 0.0205(12) 0.0010(10) -0.0001(10) -0.0005(10) C2 0.0166(12) 0.0189(13) 0.0198(12) 0.0002(11) 0.0006(10) 0.0006(10) C3 0.0194(13) 0.0229(14) 0.0257(14) -0.0040(11) 0.0055(10) -0.0015(11) C4 0.0244(14) 0.0302(15) 0.0221(13) -0.0018(11) 0.0073(11) -0.0065(12) C5 0.0232(14) 0.0269(14) 0.0176(12) -0.0021(11) 0.0019(10) -0.0032(12) C6 0.0192(13) 0.0196(13) 0.0229(13) 0.0001(11) -0.0029(10) -0.0010(11) C7 0.0199(14) 0.0273(15) 0.0282(14) -0.0001(12) -0.0003(11) -0.0046(12) C8 0.0183(13) 0.0246(14) 0.0243(14) 0.0020(11) 0.0028(11) -0.0016(11) C9 0.0159(13) 0.0206(13) 0.0256(13) 0.0001(11) 0.0006(10) 0.0017(10) C10 0.0177(12) 0.0170(12) 0.0218(13) 0.0018(10) 0.0017(10) -0.0023(10) C11 0.0196(13) 0.0212(13) 0.0171(12) 0.0016(10) -0.0002(10) -0.0005(11) C12 0.0172(12) 0.0211(13) 0.0185(12) 0.0020(10) 0.0010(10) 0.0006(10) C13 0.0224(14) 0.0377(17) 0.0357(16) -0.0110(14) 0.0069(12) -0.0037(13) C14 0.0291(15) 0.0285(15) 0.0254(14) -0.0023(12) -0.0027(12) -0.0022(13) C15 0.0191(14) 0.0444(18) 0.0280(15) -0.0076(13) 0.0025(11) 0.0042(13) O20 0.0215(9) 0.0304(11) 0.0247(10) -0.0006(9) 0.0012(8) -0.0007(9) O21 0.0214(10) 0.0302(11) 0.0235(9) 0.0018(9) 0.0021(8) 0.0076(9) C20 0.0184(13) 0.0228(14) 0.0237(13) -0.0043(11) -0.0028(11) 0.0002(11) C21 0.0191(13) 0.0233(14) 0.0234(13) -0.0071(11) -0.0032(11) -0.0012(11) C22 0.0204(13) 0.0295(15) 0.0239(14) -0.0075(12) -0.0013(11) -0.0005(12) C23 0.0238(15) 0.0345(17) 0.0300(15) -0.0117(13) -0.0056(12) 0.0076(13) C24 0.0303(16) 0.0317(16) 0.0317(15) -0.0022(13) -0.0091(12) 0.0091(13) C25 0.0296(16) 0.0374(17) 0.0264(15) 0.0021(13) -0.0025(12) 0.0019(13) C26 0.0221(14) 0.0287(14) 0.0258(14) -0.0018(12) -0.0030(11) 0.0045(12) O1A 0.0207(9) 0.0178(9) 0.0159(8) -0.0008(7) 0.0031(7) -0.0038(7) O2A 0.0179(8) 0.0202(9) 0.0189(8) 0.0007(7) 0.0049(7) -0.0012(7) O3A 0.0132(8) 0.0224(9) 0.0203(9) -0.0050(8) 0.0034(7) -0.0013(7) O10A 0.0155(9) 0.0246(10) 0.0222(9) 0.0001(8) -0.0004(7) 0.0016(8) N11A 0.0151(10) 0.0223(12) 0.0155(11) -0.0027(9) -0.0003(8) -0.0021(9) C1A 0.0153(12) 0.0154(12) 0.0193(12) 0.0004(10) 0.0011(10) -0.0030(10) C2A 0.0120(11) 0.0185(13) 0.0190(12) -0.0020(10) 0.0014(9) -0.0013(10) C3A 0.0143(12) 0.0209(13) 0.0233(13) -0.0028(11) 0.0035(10) -0.0011(11) C4A 0.0122(12) 0.0326(15) 0.0229(13) -0.0040(12) 0.0018(10) -0.0015(11) C5A 0.0177(13) 0.0261(14) 0.0237(13) -0.0020(11) -0.0038(10) 0.0041(11) C6A 0.0249(14) 0.0194(13) 0.0218(13) -0.0004(11) -0.0038(11) 0.0012(11) C7A 0.0290(15) 0.0209(12) 0.0208(13) 0.0043(11) 0.0002(11) -0.0035(12) C8A 0.0209(13) 0.0229(14) 0.0213(13) 0.0022(11) 0.0030(10) -0.0034(11) C9A 0.0159(12) 0.0189(12) 0.0188(12) -0.0017(10) 0.0023(10) -0.0006(10) C10A 0.0125(11) 0.0166(12) 0.0196(12) 0.0021(10) 0.0029(9) -0.0027(10) C11A 0.0175(12) 0.0205(13) 0.0188(12) -0.0022(10) -0.0016(10) 0.0008(11) C12A 0.0150(12) 0.0198(13) 0.0157(11) -0.0029(10) 0.0010(9) -0.0007(10) C13A 0.0173(13) 0.0294(15) 0.0263(13) -0.0002(12) 0.0050(10) -0.0008(11) C14A 0.0347(17) 0.0260(15) 0.0297(15) 0.0032(12) -0.0077(13) 0.0043(13) C15A 0.0157(13) 0.0331(15) 0.0212(12) -0.0032(11) 0.0043(10) 0.0029(11) O20A 0.0172(9) 0.0274(10) 0.0272(10) 0.0038(8) 0.0020(7) -0.0045(8) O21A 0.0169(9) 0.0258(10) 0.0244(9) -0.0033(8) 0.0004(7) 0.0013(8) C20A 0.0178(13) 0.0196(12) 0.0221(13) 0.0073(11) 0.0009(10) 0.0028(11) C21A 0.0194(13) 0.0210(13) 0.0178(12) 0.0043(10) -0.0002(10) 0.0013(10) C22A 0.0177(13) 0.0369(17) 0.0268(14) 0.0007(12) 0.0047(11) -0.0037(12) C23A 0.0257(15) 0.050(2) 0.0252(15) -0.0077(14) 0.0077(12) 0.0017(14) C24A 0.0261(15) 0.0386(17) 0.0256(14) -0.0074(13) 0.0003(12) -0.0005(13) C25A 0.0185(13) 0.0276(14) 0.0243(13) 0.0008(11) -0.0001(11) -0.0030(11) C26A 0.0170(12) 0.0247(13) 0.0181(12) 0.0042(10) 0.0016(10) 0.0017(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C1 O1 O2 112.02(18) C3 O2 O1 107.87(18) C2 O3 C3 113.4(2) C10 N11 C2 126.6(2) O1 C1 C2 110.1(2) O1 C1 C11 107.2(2) O1 C1 C12 104.2(2) C2 C1 C11 112.1(2) C2 C1 C12 110.8(2) C12 C1 C11 112.1(2) O3 C2 N11 108.3(2) O3 C2 C1 113.6(2) N11 C2 C1 112.2(2) O2 C3 O3 108.0(2) O2 C3 C4 111.8(2) O2 C3 C13 104.8(2) O3 C3 C4 110.9(2) O3 C3 C13 107.0(2) C13 C3 C4 113.8(2) C5 C4 C3 113.9(2) C4 C5 C11 115.8(2) C7 C6 C11 111.9(2) C7 C6 C14 109.7(2) C14 C6 C11 110.9(2) C8 C7 C6 112.5(2) C7 C8 C12 110.5(2) C10 C9 C12 113.1(2) C10 C9 C15 111.3(2) C15 C9 C12 114.1(2) O10 C10 N11 120.4(2) O10 C10 C9 119.9(2) N11 C10 C9 119.5(2) C5 C11 C1 111.9(2) C5 C11 C6 110.7(2) C6 C11 C1 112.3(2) C1 C12 C8 110.0(2) C1 C12 C9 110.4(2) C9 C12 C8 115.1(2) O20 C20 O21 124.0(3) O20 C20 C21 123.3(3) O21 C20 C21 112.8(2) C22 C21 C20 119.0(3) C22 C21 C26 119.8(3) C26 C21 C20 121.2(3) C23 C22 C21 120.0(3) C22 C23 C24 120.4(3) C25 C24 C23 119.7(3) C26 C25 C24 120.1(3) C25 C26 C21 120.0(3) C1A O1A O2A 112.26(17) C3A O2A O1A 107.61(18) C2A O3A C3A 113.45(19) C10A N11A C2A 126.7(2) O1A C1A C2A 110.5(2) O1A C1A C11A 107.4(2) O1A C1A C12A 104.3(2) C2A C1A C11A 111.6(2) C2A C1A C12A 111.0(2) C12A C1A C11A 111.8(2) O3A C2A N11A 108.6(2) O3A C2A C1A 113.8(2) N11A C2A C1A 112.6(2) O2A C3A O3A 107.51(19) O2A C3A C4A 112.4(2) O2A C3A C13A 105.1(2) O3A C3A C4A 111.1(2) O3A C3A C13A 107.6(2) C13A C3A C4A 112.9(2) C5A C4A C3A 114.6(2) C4A C5A C11A 115.7(2) C7A C6A C11A 111.9(2) C7A C6A C14A 109.8(2) C14A C6A C11A 110.9(2) C8A C7A C6A 112.5(2) C7A C8A C12A 110.4(2) C10A C9A C12A 112.6(2) C10A C9A C15A 111.4(2) C15A C9A C12A 114.1(2) O10A C10A N11A 121.5(2) O10A C10A C9A 120.2(2) N11A C10A C9A 118.2(2) C1A C11A C5A 111.9(2) C1A C11A C6A 112.9(2) C5A C11A C6A 111.1(2) C8A C12A C1A 110.7(2) C8A C12A C9A 115.0(2) C9A C12A C1A 109.8(2) O20A C20A O21A 124.2(3) O20A C20A C21A 123.5(3) O21A C20A C21A 112.4(2) C22A C21A C20A 119.4(3) C22A C21A C26A 119.5(3) C26A C21A C20A 121.0(2) C21A C22A C23A 120.1(3) C24A C23A C22A 119.9(3) C25A C24A C23A 120.0(3) C26A C25A C24A 120.1(3) C25A C26A C21A 120.3(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.470(3) O1 C1 1.462(3) O2 C3 1.417(3) O3 C2 1.418(3) O3 C3 1.433(4) O10 C10 1.250(3) N11 C2 1.460(3) N11 C10 1.333(4) C1 C2 1.526(4) C1 C11 1.546(3) C1 C12 1.536(3) C3 C4 1.538(4) C3 C13 1.512(4) C4 C5 1.529(4) C5 C11 1.542(4) C6 C7 1.528(4) C6 C11 1.543(4) C6 C14 1.535(4) C7 C8 1.526(4) C8 C12 1.538(4) C9 C10 1.508(4) C9 C12 1.536(4) C9 C15 1.530(4) O20 C20 1.220(4) O21 C20 1.322(4) C20 C21 1.492(4) C21 C22 1.392(4) C21 C26 1.393(4) C22 C23 1.381(4) C23 C24 1.390(5) C24 C25 1.389(5) C25 C26 1.388(4) O1A O2A 1.471(2) O1A C1A 1.456(3) O2A C3A 1.414(3) O3A C2A 1.417(3) O3A C3A 1.439(3) O10A C10A 1.242(3) N11A C2A 1.463(3) N11A C10A 1.339(3) C1A C2A 1.533(3) C1A C11A 1.541(3) C1A C12A 1.535(3) C3A C4A 1.535(4) C3A C13A 1.511(4) C4A C5A 1.524(4) C5A C11A 1.542(4) C6A C7A 1.528(4) C6A C11A 1.542(4) C6A C14A 1.533(4) C7A C8A 1.524(4) C8A C12A 1.526(4) C9A C10A 1.523(3) C9A C12A 1.530(3) C9A C15A 1.523(3) O20A C20A 1.217(3) O21A C20A 1.326(3) C20A C21A 1.498(4) C21A C22A 1.390(4) C21A C26A 1.392(4) C22A C23A 1.391(5) C23A C24A 1.390(4) C24A C25A 1.385(4) C25A C26A 1.384(4) 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 N11 H11 O20 0.90(4) 2.06(3) 2.958(3) 170(3) O21 H21 O10 0.87(4) 1.71(4) 2.572(3) 171(4) N11A H11B O20A 0.89(4) 2.23(4) 3.109(3) 169(3) O21A H21A O10A 0.91(5) 1.71(5) 2.596(3) 162(4) 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 O1 O2 C3 O3 -75.0(2) O1 O2 C3 C4 47.3(3) O1 O2 C3 C13 171.1(2) O1 C1 C2 O3 -53.0(3) O1 C1 C2 N11 70.3(3) O1 C1 C11 C5 69.1(3) O1 C1 C11 C6 -165.7(2) O1 C1 C12 C8 171.6(2) O1 C1 C12 C9 -60.3(3) O2 O1 C1 C2 14.7(3) O2 O1 C1 C11 -107.5(2) O2 O1 C1 C12 133.51(19) O2 C3 C4 C5 -96.7(3) O3 C3 C4 C5 23.9(3) C1 O1 O2 C3 46.1(3) C2 O3 C3 O2 35.7(3) C2 O3 C3 C4 -87.2(3) C2 O3 C3 C13 148.1(2) C2 N11 C10 O10 172.7(2) C2 N11 C10 C9 -11.5(4) C2 C1 C11 C5 -51.8(3) C2 C1 C11 C6 73.4(3) C2 C1 C12 C8 -70.0(3) C2 C1 C12 C9 58.1(3) C3 O3 C2 N11 -98.8(2) C3 O3 C2 C1 26.5(3) C3 C4 C5 C11 59.1(3) C4 C5 C11 C1 -37.7(3) C4 C5 C11 C6 -163.8(2) C6 C7 C8 C12 57.4(3) C7 C6 C11 C1 49.5(3) C7 C6 C11 C5 175.4(2) C7 C8 C12 C1 -58.4(3) C7 C8 C12 C9 176.2(2) C10 N11 C2 O3 148.3(3) C10 N11 C2 C1 22.1(4) C10 C9 C12 C1 -46.9(3) C10 C9 C12 C8 78.4(3) C11 C1 C2 O3 66.2(3) C11 C1 C2 N11 -170.5(2) C11 C1 C12 C8 56.1(3) C11 C1 C12 C9 -175.8(2) C11 C6 C7 C8 -52.7(3) C12 C1 C2 O3 -167.7(2) C12 C1 C2 N11 -44.5(3) C12 C1 C11 C5 -177.1(2) C12 C1 C11 C6 -51.9(3) C12 C9 C10 O10 -160.4(2) C12 C9 C10 N11 23.7(3) C13 C3 C4 C5 144.6(3) C14 C6 C7 C8 -176.3(2) C14 C6 C11 C1 172.4(2) C14 C6 C11 C5 -61.7(3) C15 C9 C10 O10 -30.5(4) C15 C9 C10 N11 153.6(3) C15 C9 C12 C1 -175.4(2) C15 C9 C12 C8 -50.1(3) O20 C20 C21 C22 -0.9(4) O20 C20 C21 C26 -178.9(3) O21 C20 C21 C22 179.0(3) O21 C20 C21 C26 1.0(4) C20 C21 C22 C23 -176.9(3) C20 C21 C26 C25 176.6(3) C21 C22 C23 C24 -0.2(4) C22 C21 C26 C25 -1.4(4) C22 C23 C24 C25 -0.4(5) C23 C24 C25 C26 0.1(5) C24 C25 C26 C21 0.7(5) C26 C21 C22 C23 1.1(4) O1A O2A C3A O3A -75.9(2) O1A O2A C3A C4A 46.7(3) O1A O2A C3A C13A 169.75(19) O1A C1A C2A O3A -51.2(3) O1A C1A C2A N11A 73.0(3) O1A C1A C11A C5A 69.1(3) O1A C1A C11A C6A -164.6(2) O1A C1A C12A C8A 171.3(2) O1A C1A C12A C9A -60.7(2) O2A O1A C1A C2A 14.2(3) O2A O1A C1A C11A -107.7(2) O2A O1A C1A C12A 133.57(18) O2A C3A C4A C5A -96.1(3) O3A C3A C4A C5A 24.4(3) C1A O1A O2A C3A 46.3(2) C2A O3A C3A O2A 37.7(3) C2A O3A C3A C4A -85.6(3) C2A O3A C3A C13A 150.4(2) C2A N11A C10A O10A 169.0(2) C2A N11A C10A C9A -15.2(4) C2A C1A C11A C5A -52.1(3) C2A C1A C11A C6A 74.1(3) C2A C1A C12A C8A -69.7(3) C2A C1A C12A C9A 58.3(3) C3A O3A C2A N11A -102.4(2) C3A O3A C2A C1A 23.9(3) C3A C4A C5A C11A 58.5(3) C4A C5A C11A C1A -37.4(3) C4A C5A C11A C6A -164.6(2) C6A C7A C8A C12A 57.4(3) C7A C6A C11A C1A 48.7(3) C7A C6A C11A C5A 175.4(2) C7A C8A C12A C1A -58.6(3) C7A C8A C12A C9A 176.3(2) C10A N11A C2A O3A 148.5(2) C10A N11A C2A C1A 21.6(4) C10A C9A C12A C1A -51.3(3) C10A C9A C12A C8A 74.3(3) C11A C1A C2A O3A 68.2(3) C11A C1A C2A N11A -167.6(2) C11A C1A C12A C8A 55.6(3) C11A C1A C12A C9A -176.4(2) C11A C6A C7A C8A -52.2(3) C12A C1A C2A O3A -166.4(2) C12A C1A C2A N11A -42.2(3) C12A C1A C11A C5A -177.1(2) C12A C1A C11A C6A -50.8(3) C12A C9A C10A O10A -154.4(2) C12A C9A C10A N11A 29.8(3) C13A C3A C4A C5A 145.3(2) C14A C6A C7A C8A -175.7(2) C14A C6A C11A C1A 171.6(2) C14A C6A C11A C5A -61.6(3) C15A C9A C10A O10A -24.7(4) C15A C9A C10A N11A 159.5(2) C15A C9A C12A C1A -179.5(2) C15A C9A C12A C8A -54.0(3) O20A C20A C21A C22A 9.2(4) O20A C20A C21A C26A -168.8(3) O21A C20A C21A C22A -170.8(2) O21A C20A C21A C26A 11.2(3) C20A C21A C22A C23A -178.1(3) C20A C21A C26A C25A 176.8(3) C21A C22A C23A C24A 1.0(5) C22A C21A C26A C25A -1.1(4) C22A C23A C24A C25A -0.7(5) C23A C24A C25A C26A -0.5(5) C24A C25A C26A C21A 1.4(4) C26A C21A C22A C23A -0.1(4)