#------------------------------------------------------------------------------ #$Date: 2021-11-03 00:55:54 +0200 (Wed, 03 Nov 2021) $ #$Revision: 270209 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129179.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_7129179 loop_ _publ_author_name 'Mandal, Rajib' 'Barsu, Nagaraju' 'Garai, Bholanath' 'Das, Abir' 'Perekalin, Dmitry' 'Sundararaju, Basker' _publ_section_title ; Room-temperature C--H bond alkynylation by merging cobalt and photocatalysts ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC05263B _journal_year 2021 _chemical_formula_moiety 'C31 H36 N2 O3' _chemical_formula_sum 'C31 H36 N2 O3' _chemical_formula_weight 484.62 _chemical_name_systematic 5AC _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-09-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-09-16 deposited with the CCDC. 2021-10-25 downloaded from the CCDC. ; _cell_angle_alpha 106.492(2) _cell_angle_beta 95.327(2) _cell_angle_gamma 97.944(2) _cell_formula_units_Z 2 _cell_length_a 8.2757(6) _cell_length_b 12.3903(9) _cell_length_c 13.7007(10) _cell_measurement_reflns_used 9972 _cell_measurement_temperature 273 _cell_measurement_theta_max 28.317 _cell_measurement_theta_min 2.510 _cell_volume 1321.16(17) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_unetI/netI 0.0350 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 33836 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.340 _diffrn_reflns_theta_min 2.509 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6448 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.8647. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.218 _exptl_crystal_description needle _exptl_crystal_F_000 520 _exptl_crystal_preparation 'Cobalt cataluzed annulation' _exptl_crystal_recrystallization_method 'Slow Evaporation in dichloromethane solvent' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.299 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 330 _refine_ls_number_reflns 6569 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0483 _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^)+(0.0347P)^2^+0.9323P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1179 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5179 _reflns_number_total 6569 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc05263b2.cif _cod_data_source_block 24auga_0m _cod_database_code 7129179 _shelx_shelxl_version_number 2017/1 _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 0.992 _shelx_estimated_absorpt_t_min 0.985 _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 Secondary CH2 refined with riding coordinates: C24(H24A,H24B), C26(H26A,H26B), C25(H25A,H25B), C29(H29A,H29B), C28(H28A, H28B), C27(H27A,H27B) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C13(H13), C12(H12), C15(H15), C16(H16), C17(H17), C6(H6), C4(H4), C5(H5) 2.c Idealised Me refined as rotating group: C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C22(H22A,H22B, H22C), C21(H21A,H21B,H21C) ; _shelx_res_file ; TITL 24auga_0m_a.res in P-1 24auga_0m.res created by SHELXL-2017/1 at 02:14:46 on 17-Sep-2021 REM Old TITL 24auga_0m in P-1 REM SHELXT solution in P-1 REM R1 0.126, Rweak 0.003, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C31 N2 O3 CELL 0.71073 8.2757 12.3903 13.7007 106.492 95.327 97.944 ZERR 2 0.0006 0.0009 0.001 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 62 72 4 6 L.S. 10 PLAN 5 SIZE 0.1 0.2 0.2 TEMP 0 LIST 6 fmap 2 acta REM REM REM WGHT 0.034700 0.932300 FVAR 0.98542 O2 4 0.371556 0.673411 0.706658 11.00000 0.01586 0.01506 = 0.01773 0.00443 0.00194 0.00109 O3 4 0.107286 0.679054 0.732193 11.00000 0.01807 0.02377 = 0.03048 0.01018 0.00519 0.00242 O1 4 0.314393 0.314458 0.743134 11.00000 0.03701 0.01977 = 0.01703 0.00781 0.00073 0.00370 N1 3 0.326860 0.488307 0.719180 11.00000 0.01643 0.01673 = 0.01192 0.00520 0.00065 0.00111 N2 3 0.647586 0.578400 0.812764 11.00000 0.01852 0.02436 = 0.01632 0.00831 0.00260 0.00288 C9 1 0.330843 0.557365 0.655055 11.00000 0.01272 0.01524 = 0.01719 0.00555 0.00151 0.00189 C18 1 0.526537 0.586468 0.874398 11.00000 0.01950 0.01506 = 0.01448 0.00613 0.00212 0.00363 C7 1 0.277430 0.394234 0.506841 11.00000 0.01097 0.01873 = 0.01495 0.00544 0.00132 0.00274 C8 1 0.307986 0.517255 0.552214 11.00000 0.01239 0.01742 = 0.01661 0.00732 0.00140 0.00170 C10 1 0.360900 0.540191 0.829125 11.00000 0.02036 0.01510 = 0.01247 0.00548 0.00135 0.00382 C14 1 0.558319 0.640215 0.982412 11.00000 0.02374 0.01604 = 0.01490 0.00703 0.00090 0.00369 C2 1 0.273891 0.320442 0.569391 11.00000 0.01253 0.01867 = 0.01523 0.00608 0.00105 0.00229 C1 1 0.305678 0.369501 0.681740 11.00000 0.01533 0.01791 = 0.01679 0.00631 0.00194 0.00114 C11 1 0.235806 0.544852 0.887607 11.00000 0.01809 0.01985 = 0.01911 0.00788 0.00292 0.00389 AFIX 43 H11 2 0.128021 0.514211 0.856573 11.00000 -1.20000 AFIX 0 C19 1 0.245425 0.728132 0.743008 11.00000 0.02007 0.01751 = 0.01585 0.00753 0.00295 0.00394 C24 1 0.313827 0.596490 0.486526 11.00000 0.01570 0.02015 = 0.01745 0.00933 0.00164 0.00187 AFIX 23 H24A 2 0.376941 0.568621 0.431225 11.00000 -1.20000 H24B 2 0.371425 0.671484 0.527986 11.00000 -1.20000 AFIX 0 C13 1 0.426825 0.642852 1.041842 11.00000 0.02927 0.01916 = 0.01348 0.00490 0.00396 0.00813 AFIX 43 H13 2 0.447708 0.676464 1.112689 11.00000 -1.20000 AFIX 0 C3 1 0.243489 0.200133 0.523547 11.00000 0.01804 0.01867 = 0.01924 0.00604 0.00271 0.00315 C12 1 0.269547 0.596160 0.995330 11.00000 0.02466 0.02393 = 0.01904 0.00843 0.00830 0.00787 AFIX 43 H12 2 0.183814 0.598090 1.034795 11.00000 -1.20000 AFIX 0 C15 1 0.723355 0.689193 1.026030 11.00000 0.02871 0.01976 = 0.01563 0.00597 -0.00214 0.00175 AFIX 43 H15 2 0.749907 0.725541 1.096287 11.00000 -1.20000 AFIX 0 C16 1 0.843091 0.682211 0.963226 11.00000 0.02072 0.02998 = 0.02353 0.01153 -0.00353 -0.00364 AFIX 43 H16 2 0.952142 0.714541 0.990050 11.00000 -1.20000 AFIX 0 C26 1 0.155092 0.663861 0.353382 11.00000 0.02002 0.02014 = 0.01877 0.00850 -0.00040 0.00213 AFIX 23 H26A 2 0.215309 0.620853 0.302770 11.00000 -1.20000 H26B 2 0.044839 0.659243 0.319723 11.00000 -1.20000 AFIX 0 C17 1 0.798924 0.625265 0.857127 11.00000 0.01899 0.03199 = 0.02181 0.01247 0.00282 0.00122 AFIX 43 H17 2 0.882309 0.620542 0.815812 11.00000 -1.20000 AFIX 0 C25 1 0.143398 0.608483 0.439721 11.00000 0.01621 0.02169 = 0.02058 0.01033 0.00119 0.00152 AFIX 23 H25A 2 0.075057 0.533481 0.412783 11.00000 -1.20000 H25B 2 0.090890 0.654521 0.493171 11.00000 -1.20000 AFIX 0 C6 1 0.254523 0.346507 0.399267 11.00000 0.01824 0.02346 = 0.01588 0.00774 0.00177 0.00434 AFIX 43 H6 2 0.259686 0.394071 0.357537 11.00000 -1.20000 AFIX 0 C29 1 0.132945 0.842083 0.230616 11.00000 0.02665 0.02286 = 0.02161 0.01017 0.00084 0.00182 AFIX 23 H29A 2 0.054924 0.880793 0.269956 11.00000 -1.20000 H29B 2 0.078739 0.764513 0.194202 11.00000 -1.20000 AFIX 0 C28 1 0.281074 0.838812 0.304078 11.00000 0.02447 0.01962 = 0.02291 0.00929 0.00325 0.00260 AFIX 23 H28A 2 0.341059 0.916085 0.334655 11.00000 -1.20000 H28B 2 0.353796 0.794351 0.264619 11.00000 -1.20000 AFIX 0 C4 1 0.217310 0.158129 0.417215 11.00000 0.02794 0.01657 = 0.01982 0.00096 0.00150 0.00296 AFIX 43 H4 2 0.194189 0.079515 0.386045 11.00000 -1.20000 AFIX 0 C20 1 0.309422 0.854266 0.794731 11.00000 0.02469 0.01760 = 0.02186 0.00621 0.00394 0.00399 C5 1 0.224698 0.230482 0.355801 11.00000 0.02730 0.02557 = 0.01442 0.00220 0.00088 0.00554 AFIX 43 H5 2 0.209227 0.199671 0.284630 11.00000 -1.20000 AFIX 0 C27 1 0.239830 0.788622 0.390413 11.00000 0.02697 0.01992 = 0.01903 0.00717 -0.00011 0.00186 AFIX 23 H27A 2 0.340915 0.795039 0.435175 11.00000 -1.20000 H27B 2 0.168880 0.833843 0.430864 11.00000 -1.20000 AFIX 0 C23 1 0.458995 0.869020 0.875570 11.00000 0.03365 0.02132 = 0.02290 0.00237 -0.00137 0.00058 AFIX 137 H23A 2 0.426370 0.834920 0.927038 11.00000 -1.50000 H23B 2 0.500792 0.948930 0.907184 11.00000 -1.50000 H23C 2 0.543288 0.832429 0.843004 11.00000 -1.50000 AFIX 0 C31 1 0.239220 0.115320 0.583656 11.00000 0.03646 0.01708 = 0.02333 0.00739 0.00426 0.00289 AFIX 137 H31A 2 0.346442 0.122957 0.620864 11.00000 -1.50000 H31B 2 0.207753 0.039249 0.537249 11.00000 -1.50000 H31C 2 0.160746 0.129715 0.631151 11.00000 -1.50000 AFIX 0 C30 1 0.181638 0.903267 0.152685 11.00000 0.03826 0.02378 = 0.02339 0.01152 0.00407 0.00550 AFIX 137 H30A 2 0.084634 0.905432 0.109529 11.00000 -1.50000 H30B 2 0.254460 0.862980 0.111161 11.00000 -1.50000 H30C 2 0.236432 0.979852 0.188376 11.00000 -1.50000 AFIX 0 C22 1 0.360409 0.907628 0.711646 11.00000 0.04749 0.01966 = 0.02924 0.01168 0.00294 0.00004 AFIX 137 H22A 2 0.447731 0.873028 0.681049 11.00000 -1.50000 H22B 2 0.397802 0.988249 0.742090 11.00000 -1.50000 H22C 2 0.267622 0.895021 0.659774 11.00000 -1.50000 AFIX 0 C21 1 0.173038 0.909747 0.845827 11.00000 0.03614 0.02512 = 0.04943 0.00104 0.01310 0.00932 AFIX 137 H21A 2 0.081244 0.901884 0.794557 11.00000 -1.50000 H21B 2 0.213639 0.989344 0.879953 11.00000 -1.50000 H21C 2 0.138356 0.872945 0.895144 11.00000 -1.50000 AFIX 0 HKLF 4 REM 24auga_0m_a.res in P-1 REM R1 = 0.0483 for 5179 Fo > 4sig(Fo) and 0.0669 for all 6569 data REM 330 parameters refined using 0 restraints END WGHT 0.0347 0.9323 REM Highest difference peak 0.299, deepest hole -0.256, 1-sigma level 0.052 Q1 1 0.2884 0.4605 0.5331 11.00000 0.05 0.30 Q2 1 0.1667 0.6392 0.4022 11.00000 0.05 0.30 Q3 1 0.2841 0.3609 0.5416 11.00000 0.05 0.30 Q4 1 0.1977 0.7262 0.3764 11.00000 0.05 0.29 Q5 1 0.2881 0.7959 0.7761 11.00000 0.05 0.28 ; _shelx_res_checksum 12722 _olex2_submission_original_sample_id BSRM-3890 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-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 O2 O 0.37156(12) 0.67341(8) 0.70666(7) 0.0165(2) Uani 1 1 d . . . . . O3 O 0.10729(13) 0.67905(9) 0.73219(8) 0.0237(2) Uani 1 1 d . . . . . O1 O 0.31439(14) 0.31446(9) 0.74313(8) 0.0244(2) Uani 1 1 d . . . . . N1 N 0.32686(14) 0.48831(10) 0.71918(8) 0.0151(2) Uani 1 1 d . . . . . N2 N 0.64759(15) 0.57840(11) 0.81276(9) 0.0193(3) Uani 1 1 d . . . . . C9 C 0.33084(16) 0.55737(11) 0.65505(10) 0.0150(3) Uani 1 1 d . . . . . C18 C 0.52654(17) 0.58647(11) 0.87440(10) 0.0159(3) Uani 1 1 d . . . . . C7 C 0.27743(16) 0.39423(12) 0.50684(10) 0.0148(3) Uani 1 1 d . . . . . C8 C 0.30799(16) 0.51726(12) 0.55221(10) 0.0151(3) Uani 1 1 d . . . . . C10 C 0.36090(17) 0.54019(11) 0.82912(10) 0.0157(3) Uani 1 1 d . . . . . C14 C 0.55832(18) 0.64022(12) 0.98241(10) 0.0178(3) Uani 1 1 d . . . . . C2 C 0.27389(16) 0.32044(12) 0.56939(10) 0.0154(3) Uani 1 1 d . . . . . C1 C 0.30568(17) 0.36950(12) 0.68174(10) 0.0166(3) Uani 1 1 d . . . . . C11 C 0.23581(18) 0.54485(12) 0.88761(11) 0.0185(3) Uani 1 1 d . . . . . H11 H 0.128021 0.514211 0.856573 0.022 Uiso 1 1 calc R . . . . C19 C 0.24543(17) 0.72813(12) 0.74301(10) 0.0172(3) Uani 1 1 d . . . . . C24 C 0.31383(17) 0.59649(12) 0.48653(11) 0.0172(3) Uani 1 1 d . . . . . H24A H 0.376941 0.568621 0.431225 0.021 Uiso 1 1 calc R . . . . H24B H 0.371425 0.671484 0.527986 0.021 Uiso 1 1 calc R . . . . C13 C 0.42682(19) 0.64285(12) 1.04184(11) 0.0202(3) Uani 1 1 d . . . . . H13 H 0.447708 0.676464 1.112689 0.024 Uiso 1 1 calc R . . . . C3 C 0.24349(17) 0.20013(12) 0.52355(11) 0.0186(3) Uani 1 1 d . . . . . C12 C 0.26955(19) 0.59616(13) 0.99533(11) 0.0214(3) Uani 1 1 d . . . . . H12 H 0.183814 0.598090 1.034795 0.026 Uiso 1 1 calc R . . . . C15 C 0.72335(19) 0.68919(13) 1.02603(11) 0.0218(3) Uani 1 1 d . . . . . H15 H 0.749907 0.725541 1.096287 0.026 Uiso 1 1 calc R . . . . C16 C 0.84309(19) 0.68221(14) 0.96323(12) 0.0252(3) Uani 1 1 d . . . . . H16 H 0.952142 0.714541 0.990050 0.030 Uiso 1 1 calc R . . . . C26 C 0.15509(18) 0.66386(12) 0.35338(11) 0.0194(3) Uani 1 1 d . . . . . H26A H 0.215309 0.620853 0.302770 0.023 Uiso 1 1 calc R . . . . H26B H 0.044839 0.659243 0.319723 0.023 Uiso 1 1 calc R . . . . C17 C 0.79892(19) 0.62527(14) 0.85713(12) 0.0237(3) Uani 1 1 d . . . . . H17 H 0.882309 0.620542 0.815812 0.028 Uiso 1 1 calc R . . . . C25 C 0.14340(17) 0.60848(13) 0.43972(11) 0.0189(3) Uani 1 1 d . . . . . H25A H 0.075057 0.533481 0.412783 0.023 Uiso 1 1 calc R . . . . H25B H 0.090890 0.654521 0.493171 0.023 Uiso 1 1 calc R . . . . C6 C 0.25452(17) 0.34651(13) 0.39927(11) 0.0188(3) Uani 1 1 d . . . . . H6 H 0.259686 0.394071 0.357537 0.023 Uiso 1 1 calc R . . . . C29 C 0.13295(19) 0.84208(13) 0.23062(12) 0.0234(3) Uani 1 1 d . . . . . H29A H 0.054924 0.880793 0.269956 0.028 Uiso 1 1 calc R . . . . H29B H 0.078739 0.764513 0.194202 0.028 Uiso 1 1 calc R . . . . C28 C 0.28107(19) 0.83881(13) 0.30408(11) 0.0218(3) Uani 1 1 d . . . . . H28A H 0.341059 0.916085 0.334655 0.026 Uiso 1 1 calc R . . . . H28B H 0.353796 0.794351 0.264619 0.026 Uiso 1 1 calc R . . . . C4 C 0.21731(19) 0.15813(13) 0.41721(11) 0.0226(3) Uani 1 1 d . . . . . H4 H 0.194189 0.079515 0.386045 0.027 Uiso 1 1 calc R . . . . C20 C 0.30942(19) 0.85427(12) 0.79473(11) 0.0212(3) Uani 1 1 d . . . . . C5 C 0.22470(19) 0.23048(13) 0.35580(11) 0.0233(3) Uani 1 1 d . . . . . H5 H 0.209227 0.199671 0.284630 0.028 Uiso 1 1 calc R . . . . C27 C 0.23983(19) 0.78862(13) 0.39041(11) 0.0221(3) Uani 1 1 d . . . . . H27A H 0.340915 0.795039 0.435175 0.027 Uiso 1 1 calc R . . . . H27B H 0.168880 0.833843 0.430864 0.027 Uiso 1 1 calc R . . . . C23 C 0.4590(2) 0.86902(14) 0.87557(12) 0.0276(3) Uani 1 1 d . . . . . H23A H 0.426370 0.834920 0.927038 0.041 Uiso 1 1 calc GR . . . . H23B H 0.500792 0.948930 0.907184 0.041 Uiso 1 1 calc GR . . . . H23C H 0.543288 0.832429 0.843004 0.041 Uiso 1 1 calc GR . . . . C31 C 0.2392(2) 0.11532(13) 0.58366(12) 0.0255(3) Uani 1 1 d . . . . . H31A H 0.346442 0.122957 0.620864 0.038 Uiso 1 1 calc GR . . . . H31B H 0.207753 0.039249 0.537249 0.038 Uiso 1 1 calc GR . . . . H31C H 0.160746 0.129715 0.631151 0.038 Uiso 1 1 calc GR . . . . C30 C 0.1816(2) 0.90327(14) 0.15269(12) 0.0275(3) Uani 1 1 d . . . . . H30A H 0.084634 0.905432 0.109529 0.041 Uiso 1 1 calc GR . . . . H30B H 0.254460 0.862980 0.111161 0.041 Uiso 1 1 calc GR . . . . H30C H 0.236432 0.979852 0.188376 0.041 Uiso 1 1 calc GR . . . . C22 C 0.3604(2) 0.90763(14) 0.71165(13) 0.0320(4) Uani 1 1 d . . . . . H22A H 0.447731 0.873028 0.681049 0.048 Uiso 1 1 calc GR . . . . H22B H 0.397802 0.988249 0.742090 0.048 Uiso 1 1 calc GR . . . . H22C H 0.267622 0.895021 0.659774 0.048 Uiso 1 1 calc GR . . . . C21 C 0.1730(2) 0.90975(15) 0.84583(16) 0.0382(4) Uani 1 1 d . . . . . H21A H 0.081244 0.901884 0.794557 0.057 Uiso 1 1 calc GR . . . . H21B H 0.213639 0.989344 0.879953 0.057 Uiso 1 1 calc GR . . . . H21C H 0.138356 0.872945 0.895144 0.057 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 O2 0.0159(5) 0.0151(5) 0.0177(5) 0.0044(4) 0.0019(4) 0.0011(4) O3 0.0181(5) 0.0238(5) 0.0305(6) 0.0102(5) 0.0052(4) 0.0024(4) O1 0.0370(6) 0.0198(5) 0.0170(5) 0.0078(4) 0.0007(4) 0.0037(4) N1 0.0164(6) 0.0167(6) 0.0119(5) 0.0052(4) 0.0006(4) 0.0011(4) N2 0.0185(6) 0.0244(6) 0.0163(6) 0.0083(5) 0.0026(5) 0.0029(5) C9 0.0127(6) 0.0152(6) 0.0172(6) 0.0056(5) 0.0015(5) 0.0019(5) C18 0.0195(7) 0.0151(6) 0.0145(6) 0.0061(5) 0.0021(5) 0.0036(5) C7 0.0110(6) 0.0187(6) 0.0150(6) 0.0054(5) 0.0013(5) 0.0027(5) C8 0.0124(6) 0.0174(6) 0.0166(6) 0.0073(5) 0.0014(5) 0.0017(5) C10 0.0204(7) 0.0151(6) 0.0125(6) 0.0055(5) 0.0013(5) 0.0038(5) C14 0.0237(7) 0.0160(6) 0.0149(6) 0.0070(5) 0.0009(5) 0.0037(5) C2 0.0125(6) 0.0187(6) 0.0152(6) 0.0061(5) 0.0011(5) 0.0023(5) C1 0.0153(6) 0.0179(6) 0.0168(6) 0.0063(5) 0.0019(5) 0.0011(5) C11 0.0181(7) 0.0198(7) 0.0191(7) 0.0079(6) 0.0029(5) 0.0039(5) C19 0.0201(7) 0.0175(6) 0.0158(6) 0.0075(5) 0.0030(5) 0.0039(5) C24 0.0157(6) 0.0202(7) 0.0174(6) 0.0093(5) 0.0016(5) 0.0019(5) C13 0.0293(8) 0.0192(7) 0.0135(6) 0.0049(5) 0.0040(6) 0.0081(6) C3 0.0180(7) 0.0187(7) 0.0192(7) 0.0060(5) 0.0027(5) 0.0032(5) C12 0.0247(7) 0.0239(7) 0.0190(7) 0.0084(6) 0.0083(6) 0.0079(6) C15 0.0287(8) 0.0198(7) 0.0156(7) 0.0060(5) -0.0021(6) 0.0017(6) C16 0.0207(7) 0.0300(8) 0.0235(8) 0.0115(6) -0.0035(6) -0.0036(6) C26 0.0200(7) 0.0201(7) 0.0188(7) 0.0085(6) -0.0004(5) 0.0021(5) C17 0.0190(7) 0.0320(8) 0.0218(7) 0.0125(6) 0.0028(6) 0.0012(6) C25 0.0162(7) 0.0217(7) 0.0206(7) 0.0103(6) 0.0012(5) 0.0015(5) C6 0.0182(7) 0.0235(7) 0.0159(6) 0.0077(6) 0.0018(5) 0.0043(5) C29 0.0267(8) 0.0229(7) 0.0216(7) 0.0102(6) 0.0008(6) 0.0018(6) C28 0.0245(8) 0.0196(7) 0.0229(7) 0.0093(6) 0.0032(6) 0.0026(6) C4 0.0279(8) 0.0166(7) 0.0198(7) 0.0010(6) 0.0015(6) 0.0030(6) C20 0.0247(7) 0.0176(7) 0.0219(7) 0.0062(6) 0.0039(6) 0.0040(6) C5 0.0273(8) 0.0256(8) 0.0144(7) 0.0022(6) 0.0009(6) 0.0055(6) C27 0.0270(8) 0.0199(7) 0.0190(7) 0.0072(6) -0.0001(6) 0.0019(6) C23 0.0337(9) 0.0213(7) 0.0229(8) 0.0024(6) -0.0014(6) 0.0006(6) C31 0.0365(9) 0.0171(7) 0.0233(7) 0.0074(6) 0.0043(6) 0.0029(6) C30 0.0383(9) 0.0238(8) 0.0234(8) 0.0115(6) 0.0041(7) 0.0055(7) C22 0.0475(11) 0.0197(8) 0.0292(8) 0.0117(7) 0.0029(7) 0.0000(7) C21 0.0361(10) 0.0251(8) 0.0494(11) 0.0010(8) 0.0131(8) 0.0093(7) 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' 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 C19 O2 C9 116.90(11) . . ? C9 N1 C10 119.51(11) . . ? C9 N1 C1 122.57(11) . . ? C1 N1 C10 117.67(11) . . ? C17 N2 C18 117.10(12) . . ? O2 C9 N1 114.07(11) . . ? C8 C9 O2 121.90(12) . . ? C8 C9 N1 123.91(12) . . ? N2 C18 C10 118.90(12) . . ? N2 C18 C14 122.98(13) . . ? C10 C18 C14 118.12(12) . . ? C2 C7 C8 120.97(12) . . ? C6 C7 C8 119.92(12) . . ? C6 C7 C2 119.09(12) . . ? C9 C8 C7 117.04(12) . . ? C9 C8 C24 121.53(12) . . ? C7 C8 C24 121.43(12) . . ? C18 C10 N1 118.53(12) . . ? C11 C10 N1 120.35(13) . . ? C11 C10 C18 121.11(13) . . ? C13 C14 C18 119.80(13) . . ? C15 C14 C18 117.51(13) . . ? C15 C14 C13 122.69(13) . . ? C7 C2 C1 119.50(12) . . ? C7 C2 C3 120.16(12) . . ? C3 C2 C1 120.32(12) . . ? O1 C1 N1 118.91(12) . . ? O1 C1 C2 125.24(13) . . ? N1 C1 C2 115.85(11) . . ? C10 C11 C12 120.21(14) . . ? O2 C19 C20 110.24(12) . . ? O3 C19 O2 122.35(13) . . ? O3 C19 C20 127.41(13) . . ? C8 C24 C25 114.10(11) . . ? C12 C13 C14 120.14(13) . . ? C2 C3 C31 123.89(13) . . ? C4 C3 C2 118.11(13) . . ? C4 C3 C31 118.01(13) . . ? C13 C12 C11 120.59(13) . . ? C16 C15 C14 118.95(13) . . ? C15 C16 C17 119.09(14) . . ? C27 C26 C25 113.57(12) . . ? N2 C17 C16 124.36(14) . . ? C26 C25 C24 111.98(11) . . ? C5 C6 C7 120.30(13) . . ? C28 C29 C30 112.27(13) . . ? C29 C28 C27 115.12(13) . . ? C3 C4 C5 121.75(13) . . ? C19 C20 C23 109.60(12) . . ? C19 C20 C22 107.81(12) . . ? C19 C20 C21 109.12(13) . . ? C22 C20 C23 109.93(13) . . ? C21 C20 C23 110.02(14) . . ? C21 C20 C22 110.32(14) . . ? C6 C5 C4 120.55(13) . . ? C26 C27 C28 114.25(12) . . ? 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 O2 C9 1.3876(16) . ? O2 C19 1.3776(17) . ? O3 C19 1.1933(17) . ? O1 C1 1.2271(16) . ? N1 C9 1.3891(17) . ? N1 C10 1.4432(17) . ? N1 C1 1.3943(17) . ? N2 C18 1.3651(18) . ? N2 C17 1.3162(19) . ? C9 C8 1.3398(19) . ? C18 C10 1.4197(19) . ? C18 C14 1.4221(19) . ? C7 C8 1.4492(19) . ? C7 C2 1.4189(18) . ? C7 C6 1.4072(19) . ? C8 C24 1.5075(18) . ? C10 C11 1.3643(19) . ? C14 C13 1.417(2) . ? C14 C15 1.416(2) . ? C2 C1 1.4688(19) . ? C2 C3 1.4196(19) . ? C11 C12 1.415(2) . ? C19 C20 1.516(2) . ? C24 C25 1.5384(19) . ? C13 C12 1.365(2) . ? C3 C4 1.386(2) . ? C3 C31 1.507(2) . ? C15 C16 1.367(2) . ? C16 C17 1.411(2) . ? C26 C25 1.5308(19) . ? C26 C27 1.526(2) . ? C6 C5 1.368(2) . ? C29 C28 1.525(2) . ? C29 C30 1.527(2) . ? C28 C27 1.528(2) . ? C4 C5 1.392(2) . ? C20 C23 1.536(2) . ? C20 C22 1.533(2) . ? C20 C21 1.525(2) . ?