#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:50:34 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205058 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229939.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_7229939 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' _chemical_formula_sum 'C15 H23 N O4' _chemical_formula_weight 281.34 _chemical_name_common 11-Azaart _chemical_name_systematic 11-azaartemisinin _space_group_crystal_system trigonal _space_group_IT_number 145 _space_group_name_Hall 'P 32' _space_group_name_H-M_alt 'P 32' _symmetry_space_group_name_Hall 'P 32' _symmetry_space_group_name_H-M 'P 32' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2017-08-04 _audit_creation_method ; Olex2 1.2 (compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370) ; _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 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 11.71759(15) _cell_length_b 11.71759(15) _cell_length_c 9.48728(13) _cell_measurement_reflns_used 4018 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 74.9010 _cell_measurement_theta_min 6.3710 _cell_volume 1128.10(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3587 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 36.00 62.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -94.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega 77.00 103.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -94.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega 26.00 77.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -94.0000 60.0000 51 #__ type_ start__ end____ width___ exp.time_ 4 omega 123.00 170.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 30.0000 -60.0000 47 #__ type_ start__ end____ width___ exp.time_ 5 omega 127.00 177.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 77.0000 -120.0000 50 #__ type_ start__ end____ width___ exp.time_ 6 omega 119.00 174.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 77.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 7 omega 82.00 107.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 61.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 8 omega 83.00 118.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 45.0000 -120.0000 35 #__ type_ start__ end____ width___ exp.time_ 9 omega 85.00 111.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 45.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 77.00 103.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 77.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 80.00 106.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 61.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 80.00 126.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 61.0000 -90.0000 46 #__ type_ start__ end____ width___ exp.time_ 13 omega 78.00 104.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 77.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega 102.00 177.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 111.0000 30.0000 75 #__ type_ start__ end____ width___ exp.time_ 15 omega 33.00 87.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 110.5703 -30.0000 -120.0000 54 #__ type_ start__ end____ width___ exp.time_ 16 omega 64.00 94.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9453 -125.0000 -150.0000 30 #__ type_ start__ end____ width___ exp.time_ 17 omega 23.00 54.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9453 -125.0000 -150.0000 31 #__ type_ start__ end____ width___ exp.time_ 18 omega -43.00 -12.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 -57.0000 -150.0000 31 #__ type_ start__ end____ width___ exp.time_ 19 omega -75.00 -48.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 -57.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 20 omega -111.00 33.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 0.0000 -180.0000 144 #__ type_ start__ end____ width___ exp.time_ 21 omega -108.00 -83.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 -133.0000 124.0000 25 #__ type_ start__ end____ width___ exp.time_ 22 omega -122.00 -89.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9453 -89.0000 157.0000 33 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1415895000 _diffrn_orient_matrix_UB_12 -0.1119422000 _diffrn_orient_matrix_UB_13 -0.0292878000 _diffrn_orient_matrix_UB_21 0.0549017000 _diffrn_orient_matrix_UB_22 -0.0798797000 _diffrn_orient_matrix_UB_23 -0.0732449000 _diffrn_orient_matrix_UB_31 -0.0004273000 _diffrn_orient_matrix_UB_32 -0.0640041000 _diffrn_orient_matrix_UB_33 0.1418938000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_unetI/netI 0.0187 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5621 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.285 _diffrn_reflns_theta_min 4.357 _diffrn_source '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 0.732 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.154 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details ; Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 2647 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0238 _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^)+(0.0299P)^2^+0.1784P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.0582 _reflns_Friedel_coverage 0.968 _reflns_Friedel_fraction_full 0.968 _reflns_Friedel_fraction_max 0.967 _reflns_number_gt 2604 _reflns_number_total 2647 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block madiha1cult_cpd1 _cod_database_code 7229939 _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. ; _shelx_estimated_absorpt_t_max 0.917 _shelx_estimated_absorpt_t_min 0.898 _reflns_odcompleteness_completeness 99.93 _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, All N(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) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: N11(H11) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; madiha8cult.res created by SHELXL-2014/7 TITL madiha8CuLT in P31 #144 REM reset to P31 #144 CELL 1.54184 11.71759 11.71759 9.48728 90 90 120 ZERR 3 0.00015 0.00015 0.00013 0 0 0 LATT -1 SYMM -Y,+X-Y,0.667+Z SYMM +Y-X,-X,0.333+Z SFAC C H N O UNIT 45 69 3 12 L.S. 4 PLAN 20 SIZE 0.12 0.15 0.15 TEMP -173 CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT 4 9 2 OMIT -1 9 -7 OMIT 1 5 -7 OMIT 1 8 1 OMIT -3 5 2 REM REM REM WGHT 0.029900 0.178400 FVAR 11.82920 O1 4 0.169599 0.421247 0.660772 11.00000 0.02179 0.01425 = 0.02668 -0.00081 0.00541 0.00862 O2 4 0.034843 0.320829 0.699350 11.00000 0.02131 0.01838 = 0.02551 0.00292 0.00639 0.00975 O3 4 0.066499 0.142738 0.686192 11.00000 0.02279 0.01508 = 0.01761 0.00193 0.00376 0.00940 O10 4 0.022968 0.245049 0.236288 11.00000 0.02308 0.02418 = 0.02169 0.00261 -0.00446 0.00487 N11 3 0.074697 0.193391 0.445626 11.00000 0.01696 0.01303 = 0.01864 -0.00049 -0.00010 0.00445 AFIX 43 H11 2 0.006804 0.113519 0.435014 11.00000 -1.20000 AFIX 0 C1 1 0.243409 0.361087 0.604346 11.00000 0.01991 0.01453 = 0.01836 -0.00296 0.00000 0.00973 C2 1 0.152982 0.214415 0.571724 11.00000 0.01769 0.01465 = 0.01764 0.00036 0.00154 0.00775 AFIX 13 H2 2 0.210616 0.175478 0.554194 11.00000 -1.20000 AFIX 0 C3 1 0.042953 0.224233 0.781272 11.00000 0.02769 0.01810 = 0.01987 0.00031 0.00435 0.01245 C4 1 0.150465 0.284337 0.894484 11.00000 0.03549 0.02461 = 0.01793 -0.00002 0.00143 0.01263 AFIX 23 H4A 2 0.164228 0.372236 0.920165 11.00000 -1.20000 H4B 2 0.118928 0.228255 0.979760 11.00000 -1.20000 AFIX 0 C5 1 0.282913 0.299327 0.850551 11.00000 0.02884 0.02375 = 0.02062 0.00047 -0.00578 0.00924 AFIX 23 H5A 2 0.270649 0.210200 0.836085 11.00000 -1.20000 H5B 2 0.345574 0.340348 0.929631 11.00000 -1.20000 AFIX 0 C6 1 0.454639 0.356075 0.658437 11.00000 0.02090 0.02327 = 0.03324 0.00226 -0.00358 0.00993 AFIX 13 H6 2 0.413785 0.260257 0.635412 11.00000 -1.20000 AFIX 0 C7 1 0.512547 0.434576 0.523527 11.00000 0.01934 0.02079 = 0.03510 0.00124 0.00078 0.00924 AFIX 23 H7A 2 0.577602 0.412579 0.484643 11.00000 -1.20000 H7B 2 0.559873 0.529734 0.546536 11.00000 -1.20000 AFIX 0 C8 1 0.409061 0.408020 0.411383 11.00000 0.02000 0.01792 = 0.02569 -0.00074 0.00447 0.00790 AFIX 23 H8A 2 0.365581 0.314400 0.382323 11.00000 -1.20000 H8B 2 0.451875 0.463235 0.327428 11.00000 -1.20000 AFIX 0 C9 1 0.198094 0.423337 0.365742 11.00000 0.02074 0.01635 = 0.02087 0.00085 -0.00075 0.00903 AFIX 13 H9 2 0.152879 0.467460 0.410221 11.00000 -1.20000 AFIX 0 C10 1 0.092189 0.280206 0.342247 11.00000 0.01694 0.01930 = 0.01904 -0.00002 0.00231 0.00900 C11 1 0.346076 0.380826 0.717228 11.00000 0.02240 0.01735 = 0.02238 -0.00250 -0.00487 0.00689 AFIX 13 H11A 2 0.390337 0.475596 0.745859 11.00000 -1.20000 AFIX 0 C12 1 0.306010 0.439514 0.469866 11.00000 0.01807 0.01196 = 0.02101 -0.00106 -0.00018 0.00609 AFIX 13 H12 2 0.354764 0.534532 0.497768 11.00000 -1.20000 AFIX 0 C13 1 -0.093610 0.140798 0.842683 11.00000 0.03008 0.02458 = 0.02450 0.00139 0.00865 0.01265 AFIX 137 H13A 2 -0.159713 0.124558 0.770296 11.00000 -1.50000 H13B 2 -0.105168 0.187257 0.922399 11.00000 -1.50000 H13C 2 -0.104360 0.056564 0.875111 11.00000 -1.50000 AFIX 0 C14 1 0.564153 0.390956 0.766420 11.00000 0.02728 0.04999 = 0.04753 0.00971 -0.00928 0.01662 AFIX 137 H14A 2 0.634532 0.380689 0.723395 11.00000 -1.50000 H14B 2 0.528296 0.332105 0.847934 11.00000 -1.50000 H14C 2 0.599808 0.482426 0.797128 11.00000 -1.50000 AFIX 0 C15 1 0.252320 0.492814 0.224763 11.00000 0.02670 0.02153 = 0.02537 0.00540 -0.00315 0.00398 AFIX 137 H15A 2 0.293983 0.450064 0.174588 11.00000 -1.50000 H15B 2 0.317669 0.585525 0.241676 11.00000 -1.50000 H15C 2 0.180063 0.487380 0.167672 11.00000 -1.50000 AFIX 0 HKLF 4 REM madiha8CuLT in P31 #144 REM R1 = 0.0238 for 2604 Fo > 4sig(Fo) and 0.0243 for all 2647 data REM 184 parameters refined using 1 restraints END WGHT 0.0290 0.1493 REM Highest difference peak 0.154, deepest hole -0.132, 1-sigma level 0.028 Q1 1 0.2019 0.2953 0.5916 11.00000 0.05 0.15 Q2 1 0.1431 0.3526 0.3521 11.00000 0.05 0.13 Q3 1 0.2694 0.3942 0.5358 11.00000 0.05 0.12 Q4 1 0.2554 0.4360 0.4217 11.00000 0.05 0.12 Q5 1 0.3001 0.3648 0.6538 11.00000 0.05 0.11 Q6 1 0.3942 0.3603 0.6750 11.00000 0.05 0.10 Q7 1 0.1006 0.2535 0.8420 11.00000 0.05 0.09 Q8 1 0.3512 0.4228 0.4363 11.00000 0.05 0.09 Q9 1 0.6470 0.4942 0.7654 11.00000 0.05 0.09 Q10 1 0.6107 0.3372 0.6596 11.00000 0.05 0.09 Q11 1 0.2195 0.2987 0.8774 11.00000 0.05 0.09 Q12 1 0.4749 0.3792 0.5841 11.00000 0.05 0.09 Q13 1 0.2260 0.4542 0.2961 11.00000 0.05 0.09 Q14 1 0.0489 0.1037 0.4277 11.00000 0.05 0.09 Q15 1 0.0235 0.4393 0.4152 11.00000 0.05 0.08 Q16 1 -0.0535 0.3594 0.5171 11.00000 0.05 0.08 Q17 1 0.5176 0.2743 0.8278 11.00000 0.05 0.08 Q18 1 0.3123 0.3302 0.7776 11.00000 0.05 0.08 Q19 1 0.5341 0.5948 0.5145 11.00000 0.05 0.08 Q20 1 0.2654 0.4674 0.9424 11.00000 0.05 0.08 ; _shelx_res_checksum 21809 _olex2_date_sample_data_collection 2016-03-17 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 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 0.16960(13) 0.42125(12) 0.66077(14) 0.0211(3) Uani 1 1 d . O2 O 0.03484(12) 0.32083(12) 0.69935(14) 0.0218(3) Uani 1 1 d . O3 O 0.06650(12) 0.14274(12) 0.68619(12) 0.0185(3) Uani 1 1 d . O10 O 0.02297(13) 0.24505(13) 0.23629(14) 0.0261(3) Uani 1 1 d . N11 N 0.07470(14) 0.19339(14) 0.44563(15) 0.0176(3) Uani 1 1 d . H11 H 0.0068 0.1135 0.4350 0.021 Uiso 1 1 calc R C1 C 0.24341(17) 0.36109(17) 0.60435(18) 0.0171(4) Uani 1 1 d . C2 C 0.15298(17) 0.21442(17) 0.57172(18) 0.0168(4) Uani 1 1 d . H2 H 0.2106 0.1755 0.5542 0.020 Uiso 1 1 calc R C3 C 0.04295(19) 0.22423(18) 0.78127(19) 0.0214(4) Uani 1 1 d . C4 C 0.1505(2) 0.2843(2) 0.8945(2) 0.0271(4) Uani 1 1 d . H4A H 0.1642 0.3722 0.9202 0.032 Uiso 1 1 calc R H4B H 0.1189 0.2283 0.9798 0.032 Uiso 1 1 calc R C5 C 0.2829(2) 0.2993(2) 0.85055(19) 0.0261(4) Uani 1 1 d . H5A H 0.2706 0.2102 0.8361 0.031 Uiso 1 1 calc R H5B H 0.3456 0.3403 0.9296 0.031 Uiso 1 1 calc R C6 C 0.45464(19) 0.3561(2) 0.6584(2) 0.0263(4) Uani 1 1 d . H6 H 0.4138 0.2603 0.6354 0.032 Uiso 1 1 calc R C7 C 0.51255(19) 0.43458(19) 0.5235(2) 0.0254(4) Uani 1 1 d . H7A H 0.5776 0.4126 0.4846 0.031 Uiso 1 1 calc R H7B H 0.5599 0.5297 0.5465 0.031 Uiso 1 1 calc R C8 C 0.40906(18) 0.40802(18) 0.4114(2) 0.0219(4) Uani 1 1 d . H8A H 0.3656 0.3144 0.3823 0.026 Uiso 1 1 calc R H8B H 0.4519 0.4632 0.3274 0.026 Uiso 1 1 calc R C9 C 0.19809(18) 0.42334(17) 0.36574(19) 0.0194(4) Uani 1 1 d . H9 H 0.1529 0.4675 0.4102 0.023 Uiso 1 1 calc R C10 C 0.09219(17) 0.28021(17) 0.34225(18) 0.0185(4) Uani 1 1 d . C11 C 0.34608(18) 0.38083(18) 0.7172(2) 0.0221(4) Uani 1 1 d . H11A H 0.3903 0.4756 0.7459 0.026 Uiso 1 1 calc R C12 C 0.30601(17) 0.43951(17) 0.46987(18) 0.0176(4) Uani 1 1 d . H12 H 0.3548 0.5345 0.4978 0.021 Uiso 1 1 calc R C13 C -0.0936(2) 0.1408(2) 0.8427(2) 0.0268(4) Uani 1 1 d . H13A H -0.1597 0.1246 0.7703 0.040 Uiso 1 1 calc GR H13B H -0.1052 0.1873 0.9224 0.040 Uiso 1 1 calc GR H13C H -0.1044 0.0566 0.8751 0.040 Uiso 1 1 calc GR C14 C 0.5642(2) 0.3910(3) 0.7664(3) 0.0428(6) Uani 1 1 d . H14A H 0.6345 0.3807 0.7234 0.064 Uiso 1 1 calc GR H14B H 0.5283 0.3321 0.8479 0.064 Uiso 1 1 calc GR H14C H 0.5998 0.4824 0.7971 0.064 Uiso 1 1 calc GR C15 C 0.2523(2) 0.4928(2) 0.2248(2) 0.0281(4) Uani 1 1 d . H15A H 0.2940 0.4501 0.1746 0.042 Uiso 1 1 calc GR H15B H 0.3177 0.5855 0.2417 0.042 Uiso 1 1 calc GR H15C H 0.1801 0.4874 0.1677 0.042 Uiso 1 1 calc GR 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 0.0218(6) 0.0142(6) 0.0267(7) -0.0008(5) 0.0054(5) 0.0086(5) O2 0.0213(6) 0.0184(6) 0.0255(7) 0.0029(5) 0.0064(5) 0.0097(5) O3 0.0228(7) 0.0151(6) 0.0176(6) 0.0019(5) 0.0038(5) 0.0094(5) O10 0.0231(7) 0.0242(7) 0.0217(7) 0.0026(5) -0.0045(5) 0.0049(6) N11 0.0170(7) 0.0130(7) 0.0186(7) -0.0005(6) -0.0001(6) 0.0044(6) C1 0.0199(9) 0.0145(8) 0.0184(9) -0.0030(6) 0.0000(7) 0.0097(7) C2 0.0177(8) 0.0146(8) 0.0176(8) 0.0004(6) 0.0015(7) 0.0078(7) C3 0.0277(10) 0.0181(9) 0.0199(9) 0.0003(7) 0.0043(7) 0.0125(8) C4 0.0355(11) 0.0246(10) 0.0179(9) 0.0000(7) 0.0014(8) 0.0126(9) C5 0.0288(10) 0.0238(10) 0.0206(9) 0.0005(7) -0.0058(8) 0.0092(8) C6 0.0209(10) 0.0233(10) 0.0332(11) 0.0023(8) -0.0036(8) 0.0099(8) C7 0.0193(10) 0.0208(9) 0.0351(12) 0.0012(8) 0.0008(8) 0.0092(8) C8 0.0200(9) 0.0179(9) 0.0257(9) -0.0007(7) 0.0045(7) 0.0079(8) C9 0.0207(9) 0.0163(9) 0.0209(9) 0.0008(7) -0.0008(7) 0.0090(8) C10 0.0169(8) 0.0193(9) 0.0190(9) 0.0000(7) 0.0023(7) 0.0090(7) C11 0.0224(10) 0.0174(9) 0.0224(9) -0.0025(7) -0.0049(7) 0.0069(8) C12 0.0181(9) 0.0120(8) 0.0210(9) -0.0011(6) -0.0002(7) 0.0061(7) C13 0.0301(11) 0.0246(10) 0.0245(10) 0.0014(8) 0.0087(8) 0.0127(9) C14 0.0273(12) 0.0500(15) 0.0475(15) 0.0097(11) -0.0093(10) 0.0166(11) C15 0.0267(11) 0.0215(9) 0.0254(10) 0.0054(8) -0.0032(8) 0.0040(8) 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 111.29(12) C3 O2 O1 107.62(13) C2 O3 C3 113.58(13) C10 N11 C2 128.65(14) O1 C1 C2 111.73(14) O1 C1 C11 106.19(14) O1 C1 C12 103.73(13) C2 C1 C11 111.04(14) C12 C1 C2 111.12(14) C12 C1 C11 112.73(14) O3 C2 N11 108.83(14) O3 C2 C1 113.15(14) N11 C2 C1 112.36(14) O2 C3 O3 107.38(13) O2 C3 C4 112.70(15) O2 C3 C13 104.83(15) O3 C3 C4 111.00(16) O3 C3 C13 107.73(15) C13 C3 C4 112.81(16) C5 C4 C3 114.54(16) C4 C5 C11 116.24(16) C7 C6 C11 110.51(16) C7 C6 C14 109.91(17) C14 C6 C11 111.59(18) C6 C7 C8 113.24(16) C7 C8 C12 109.91(15) C10 C9 C12 113.34(14) C10 C9 C15 110.55(15) C15 C9 C12 113.49(15) O10 C10 N11 121.04(16) O10 C10 C9 121.84(16) N11 C10 C9 117.09(15) C1 C11 C6 112.08(15) C5 C11 C1 112.49(15) C5 C11 C6 111.56(16) C1 C12 C8 110.89(14) C1 C12 C9 110.11(14) C8 C12 C9 115.82(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.4676(18) O1 C1 1.463(2) O2 C3 1.415(2) O3 C2 1.435(2) O3 C3 1.437(2) O10 C10 1.226(2) N11 C2 1.452(2) N11 C10 1.353(2) C1 C2 1.533(2) C1 C11 1.539(2) C1 C12 1.528(2) C3 C4 1.533(3) C3 C13 1.514(3) C4 C5 1.530(3) C5 C11 1.534(3) C6 C7 1.523(3) C6 C11 1.543(3) C6 C14 1.529(3) C7 C8 1.524(3) C8 C12 1.532(2) C9 C10 1.524(2) C9 C12 1.540(2) C9 C15 1.529(3) 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 -77.21(16) O1 O2 C3 C4 45.34(18) O1 O2 C3 C13 168.39(13) O1 C1 C2 O3 -49.49(19) O1 C1 C2 N11 74.26(18) O1 C1 C11 C5 68.45(18) O1 C1 C11 C6 -164.88(14) O1 C1 C12 C8 168.93(14) O1 C1 C12 C9 -61.56(16) O2 O1 C1 C2 12.13(18) O2 O1 C1 C11 -109.08(14) O2 O1 C1 C12 131.91(13) O2 C3 C4 C5 -94.7(2) O3 C3 C4 C5 25.8(2) C1 O1 O2 C3 48.65(16) C2 O3 C3 O2 37.59(19) C2 O3 C3 C4 -86.00(17) C2 O3 C3 C13 150.03(15) C2 N11 C10 O10 174.58(17) C2 N11 C10 C9 -7.3(3) C2 C1 C11 C5 -53.2(2) C2 C1 C11 C6 73.48(19) C2 C1 C12 C8 -70.89(18) C2 C1 C12 C9 58.62(17) C3 O3 C2 N11 -102.38(16) C3 O3 C2 C1 23.28(19) C3 C4 C5 C11 56.9(2) C4 C5 C11 C1 -36.2(2) C4 C5 C11 C6 -163.17(16) C6 C7 C8 C12 57.8(2) C7 C6 C11 C1 50.9(2) C7 C6 C11 C5 178.12(15) C7 C8 C12 C1 -56.27(19) C7 C8 C12 C9 177.32(15) C10 N11 C2 O3 142.19(17) C10 N11 C2 C1 16.1(2) C10 C9 C12 C1 -49.69(19) C10 C9 C12 C8 77.11(19) C11 C1 C2 O3 68.86(18) C11 C1 C2 N11 -167.39(14) C11 C1 C12 C8 54.50(18) C11 C1 C12 C9 -175.99(14) C11 C6 C7 C8 -55.0(2) C12 C1 C2 O3 -164.82(14) C12 C1 C2 N11 -41.07(18) C12 C1 C11 C5 -178.62(15) C12 C1 C11 C6 -51.95(19) C12 C9 C10 O10 -157.90(16) C12 C9 C10 N11 24.0(2) C13 C3 C4 C5 146.85(17) C14 C6 C7 C8 -178.56(18) C14 C6 C11 C1 173.56(16) C14 C6 C11 C5 -59.3(2) C15 C9 C10 O10 -29.2(2) C15 C9 C10 N11 152.73(16) C15 C9 C12 C1 -176.87(15) C15 C9 C12 C8 -50.1(2)