#------------------------------------------------------------------------------ #$Date: 2025-06-24 02:14:22 +0300 (Tue, 24 Jun 2025) $ #$Revision: 300166 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/49/1574922.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_1574922 loop_ _publ_author_name 'Ray, Ranay Kumar' 'Sudhadevi Antharjanam, P. K.' 'Chakraborty, Debashis' _publ_section_title ; Efficient and Controlled Ring-Opening Copolymerization of Cyclohexene Oxide with Cyclic Anhydrides Catalyzed by Proline-based Chiral Alkyl Al(III) Compounds ; _journal_name_full 'Faraday Discussions' _journal_paper_doi 10.1039/D5FD00048C _journal_year 2025 _chemical_absolute_configuration unk _chemical_formula_moiety 'C22 H27 N O3' _chemical_formula_sum 'C22 H27 N O3' _chemical_formula_weight 353.44 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-04-23 deposited with the CCDC. 2025-06-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.9084(5) _cell_length_b 9.6525(7) _cell_length_c 22.6244(15) _cell_measurement_reflns_used 9258 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.50 _cell_measurement_theta_min 2.91 _cell_volume 1945.4(2) _computing_cell_refinement 'APEX4 V8.40B (Bruker, 2021)' _computing_data_collection 'APEX4 (Bruker, v2021.4-0)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2021)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 2012) ' _computing_publication_material 'SHELXL-2019/3 (Sheldrick, 2019)' _computing_structure_refinement 'SHELXL-2019/3 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 VENTURE diffractometer equipped with PHOTON II detector' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_unetI/netI 0.0203 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 50541 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.518 _diffrn_reflns_theta_min 3.240 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.207 _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.355 _exptl_crystal_size_mid 0.198 _exptl_crystal_size_min 0.134 _refine_diff_density_max 0.362 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 2425 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.13(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 5941 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0343 _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^)+(0.0541P)^2^+0.2934P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0875 _refine_ls_wR_factor_ref 0.0887 _reflns_Friedel_coverage 0.770 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 5724 _reflns_number_total 5941 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5fd00048c2.cif _cod_data_source_block shelx _cod_database_code 1574922 _shelx_shelxl_version_number 2019/3 _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_min 0.972 _shelx_estimated_absorpt_t_max 0.989 _shelx_res_file ; TITL RKRZN1_a.res in P2(1)2(1)2(1) shelx.res created by SHELXL-2019/3 at 12:01:35 on 21-Sep-2023 CELL 0.71073 8.9084 9.6525 22.6244 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0007 0.0015 0.000 0.000 0.000 LATT -1 SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 - X, - Y, 1/2 + Z SFAC C H N O UNIT 88 108 4 12 MERG 2 OMIT 1 1 0 HTAB C20 O3 HTAB C21 O3 HTAB O2 O3 FMAP 2 PLAN 20 SIZE 0.134 0.198 0.355 ACTA BOND $H CONF L.S. 4 TEMP -173.15 WGHT 0.054100 0.293400 FVAR 0.63800 C1 1 0.537724 0.501823 0.238963 11.00000 0.01282 0.01382 = 0.01353 0.00013 -0.00081 -0.00063 AFIX 43 H1 2 0.586652 0.460977 0.205973 11.00000 -1.20000 AFIX 0 C2 1 0.382824 0.488878 0.245094 11.00000 0.01393 0.01731 = 0.01831 0.00260 -0.00228 -0.00275 AFIX 43 H2 2 0.326726 0.438461 0.216589 11.00000 -1.20000 AFIX 0 C3 1 0.310174 0.549707 0.292922 11.00000 0.01096 0.01900 = 0.02413 0.00431 0.00289 -0.00005 AFIX 43 H3 2 0.204604 0.540185 0.297250 11.00000 -1.20000 AFIX 0 C4 1 0.392255 0.624633 0.334500 11.00000 0.01584 0.01908 = 0.02010 0.00080 0.00622 0.00187 AFIX 43 H4 2 0.342651 0.667150 0.366945 11.00000 -1.20000 AFIX 0 C5 1 0.547878 0.637023 0.328302 11.00000 0.01553 0.01464 = 0.01393 -0.00107 0.00214 0.00061 AFIX 43 H5 2 0.603627 0.688487 0.356573 11.00000 -1.20000 AFIX 0 C6 1 0.621977 0.574517 0.280998 11.00000 0.01057 0.01151 = 0.01190 0.00122 0.00043 0.00022 C7 1 0.793007 0.575069 0.278689 11.00000 0.01062 0.01045 = 0.01015 -0.00061 0.00048 -0.00051 C8 1 0.849623 0.574944 0.214574 11.00000 0.01075 0.01183 = 0.01160 -0.00016 0.00017 -0.00170 C9 1 0.944209 0.474452 0.190704 11.00000 0.01738 0.01421 = 0.01536 0.00025 0.00219 0.00158 AFIX 43 H9 2 0.974954 0.398133 0.214292 11.00000 -1.20000 AFIX 0 C10 1 0.994250 0.485151 0.132215 11.00000 0.02224 0.02027 = 0.01675 -0.00388 0.00535 0.00116 AFIX 43 H10 2 1.058277 0.415787 0.116346 11.00000 -1.20000 AFIX 0 C11 1 0.951051 0.596214 0.097295 11.00000 0.02284 0.02609 = 0.01242 0.00019 0.00434 -0.00464 AFIX 43 H11 2 0.985031 0.603013 0.057600 11.00000 -1.20000 AFIX 0 C12 1 0.857408 0.697815 0.120855 11.00000 0.02130 0.02111 = 0.01536 0.00549 -0.00017 -0.00197 AFIX 43 H12 2 0.828114 0.774714 0.097323 11.00000 -1.20000 AFIX 0 C13 1 0.806818 0.686642 0.178832 11.00000 0.01511 0.01568 = 0.01537 0.00208 0.00097 0.00070 AFIX 43 H13 2 0.742205 0.755880 0.194431 11.00000 -1.20000 AFIX 0 C14 1 0.857230 0.450525 0.314842 11.00000 0.01137 0.01167 = 0.01072 0.00046 0.00008 -0.00053 AFIX 13 H14 2 0.967403 0.443473 0.306924 11.00000 -1.20000 AFIX 0 C15 1 0.785056 0.308796 0.302662 11.00000 0.01684 0.01115 = 0.01641 0.00018 -0.00220 -0.00200 AFIX 23 H15A 2 0.861068 0.234142 0.304787 11.00000 -1.20000 H15B 2 0.738058 0.307220 0.263016 11.00000 -1.20000 AFIX 0 C16 1 0.665831 0.290308 0.351209 11.00000 0.01833 0.01621 = 0.01939 0.00373 -0.00145 -0.00641 AFIX 23 H16A 2 0.569250 0.332518 0.339199 11.00000 -1.20000 H16B 2 0.649340 0.190936 0.359880 11.00000 -1.20000 AFIX 0 C17 1 0.731554 0.365104 0.404954 11.00000 0.01798 0.01927 = 0.01591 0.00441 0.00036 -0.00616 AFIX 23 H17A 2 0.651600 0.410983 0.428203 11.00000 -1.20000 H17B 2 0.786295 0.299683 0.430860 11.00000 -1.20000 AFIX 0 C18 1 0.939144 0.535602 0.411288 11.00000 0.01290 0.01800 = 0.01125 0.00033 -0.00110 0.00053 C19 1 1.024980 0.575255 0.512677 11.00000 0.01916 0.02085 = 0.01083 -0.00047 -0.00327 -0.00146 C20 1 1.035885 0.732352 0.506958 11.00000 0.04259 0.01994 = 0.01718 -0.00176 -0.00108 -0.00097 AFIX 137 H20A 2 1.082039 0.756059 0.468961 11.00000 -1.50000 H20B 2 1.097524 0.769193 0.539210 11.00000 -1.50000 H20C 2 0.935102 0.772759 0.509027 11.00000 -1.50000 AFIX 0 C21 1 1.176130 0.503811 0.504796 11.00000 0.01970 0.03115 = 0.02107 0.00079 -0.00670 0.00293 AFIX 137 H21A 2 1.162402 0.403174 0.506684 11.00000 -1.50000 H21B 2 1.244547 0.533252 0.536304 11.00000 -1.50000 H21C 2 1.218681 0.529046 0.466330 11.00000 -1.50000 AFIX 0 C22 1 0.954100 0.535033 0.571495 11.00000 0.03012 0.03228 = 0.01239 0.00114 -0.00059 -0.00341 AFIX 137 H22A 2 0.854307 0.577128 0.574617 11.00000 -1.50000 H22B 2 1.017454 0.568100 0.603975 11.00000 -1.50000 H22C 2 0.944937 0.433994 0.573733 11.00000 -1.50000 AFIX 0 N1 3 0.834600 0.467934 0.379103 11.00000 0.01371 0.01609 = 0.01035 0.00211 -0.00007 -0.00326 O1 4 0.917374 0.517434 0.469540 11.00000 0.01614 0.02727 = 0.01042 0.00123 -0.00195 -0.00460 O2 4 0.842935 0.702180 0.305189 11.00000 0.01510 0.01085 = 0.01602 -0.00230 -0.00309 -0.00217 AFIX 147 H2A 2 0.920970 0.687292 0.325039 11.00000 -1.50000 AFIX 0 O3 4 1.040103 0.606598 0.389478 11.00000 0.01329 0.02355 = 0.01300 0.00040 -0.00068 -0.00526 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM RKRZN1_a.res in P2(1)2(1)2(1) REM wR2 = 0.0887, GooF = S = 1.064, Restrained GooF = 1.064 for all data REM R1 = 0.0343 for 5724 Fo > 4sig(Fo) and 0.0364 for all 5941 data REM 239 parameters refined using 0 restraints END WGHT 0.0541 0.2934 REM Highest difference peak 0.362, deepest hole -0.199, 1-sigma level 0.045 Q1 1 0.8143 0.5737 0.2469 11.00000 0.05 0.36 Q2 1 0.9616 0.4800 0.1607 11.00000 0.05 0.34 Q3 1 0.3559 0.6005 0.3093 11.00000 0.05 0.32 Q4 1 0.4664 0.6306 0.3279 11.00000 0.05 0.31 Q5 1 0.5827 0.5982 0.3059 11.00000 0.05 0.31 Q6 1 0.8217 0.6812 0.1471 11.00000 0.05 0.30 Q7 1 0.3476 0.5256 0.2678 11.00000 0.05 0.29 Q8 1 0.4603 0.5090 0.2422 11.00000 0.05 0.28 Q9 1 0.7231 0.3043 0.3252 11.00000 0.05 0.27 Q10 1 0.8222 0.6230 0.1941 11.00000 0.05 0.27 Q11 1 0.6941 0.3322 0.3752 11.00000 0.05 0.26 Q12 1 0.5757 0.5391 0.2613 11.00000 0.05 0.26 Q13 1 0.7075 0.5704 0.2799 11.00000 0.05 0.25 Q14 1 0.9889 0.5644 0.1224 11.00000 0.05 0.25 Q15 1 0.9107 0.5368 0.2034 11.00000 0.05 0.25 Q16 1 0.9211 0.6507 0.1137 11.00000 0.05 0.24 Q17 1 0.8261 0.5148 0.2986 11.00000 0.05 0.24 Q18 1 0.7832 0.4203 0.3921 11.00000 0.05 0.24 Q19 1 1.1006 0.5361 0.5091 11.00000 0.05 0.23 Q20 1 0.8971 0.4858 0.3952 11.00000 0.05 0.23 ; _shelx_res_checksum 53059 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 C1 C 0.53772(15) 0.50182(13) 0.23896(5) 0.0134(2) Uani 1 1 d . . . . . H1 H 0.586652 0.460977 0.205973 0.016 Uiso 1 1 calc R U . . . C2 C 0.38282(15) 0.48888(15) 0.24509(6) 0.0165(2) Uani 1 1 d . . . . . H2 H 0.326726 0.438461 0.216589 0.020 Uiso 1 1 calc R U . . . C3 C 0.31017(15) 0.54971(15) 0.29292(6) 0.0180(3) Uani 1 1 d . . . . . H3 H 0.204604 0.540185 0.297250 0.022 Uiso 1 1 calc R U . . . C4 C 0.39226(16) 0.62463(15) 0.33450(6) 0.0183(3) Uani 1 1 d . . . . . H4 H 0.342651 0.667150 0.366945 0.022 Uiso 1 1 calc R U . . . C5 C 0.54788(15) 0.63702(14) 0.32830(6) 0.0147(2) Uani 1 1 d . . . . . H5 H 0.603627 0.688487 0.356573 0.018 Uiso 1 1 calc R U . . . C6 C 0.62198(13) 0.57452(13) 0.28100(5) 0.0113(2) Uani 1 1 d . . . . . C7 C 0.79301(13) 0.57507(13) 0.27869(5) 0.0104(2) Uani 1 1 d . . . . . C8 C 0.84962(14) 0.57494(13) 0.21457(5) 0.0114(2) Uani 1 1 d . . . . . C9 C 0.94421(15) 0.47445(14) 0.19070(6) 0.0156(2) Uani 1 1 d . . . . . H9 H 0.974954 0.398133 0.214292 0.019 Uiso 1 1 calc R U . . . C10 C 0.99425(17) 0.48515(15) 0.13221(6) 0.0198(3) Uani 1 1 d . . . . . H10 H 1.058277 0.415787 0.116346 0.024 Uiso 1 1 calc R U . . . C11 C 0.95105(17) 0.59621(16) 0.09730(6) 0.0204(3) Uani 1 1 d . . . . . H11 H 0.985031 0.603013 0.057600 0.025 Uiso 1 1 calc R U . . . C12 C 0.85741(16) 0.69782(16) 0.12085(6) 0.0193(3) Uani 1 1 d . . . . . H12 H 0.828114 0.774714 0.097323 0.023 Uiso 1 1 calc R U . . . C13 C 0.80682(15) 0.68664(14) 0.17883(6) 0.0154(2) Uani 1 1 d . . . . . H13 H 0.742205 0.755880 0.194431 0.018 Uiso 1 1 calc R U . . . C14 C 0.85723(14) 0.45052(13) 0.31484(5) 0.0113(2) Uani 1 1 d . . . . . H14 H 0.967403 0.443473 0.306924 0.014 Uiso 1 1 calc R U . . . C15 C 0.78506(15) 0.30880(13) 0.30266(6) 0.0148(2) Uani 1 1 d . . . . . H15A H 0.861068 0.234142 0.304787 0.018 Uiso 1 1 calc R U . . . H15B H 0.738058 0.307220 0.263016 0.018 Uiso 1 1 calc R U . . . C16 C 0.66583(16) 0.29031(15) 0.35121(6) 0.0180(3) Uani 1 1 d . . . . . H16A H 0.569250 0.332518 0.339199 0.022 Uiso 1 1 calc R U . . . H16B H 0.649340 0.190936 0.359880 0.022 Uiso 1 1 calc R U . . . C17 C 0.73155(16) 0.36510(16) 0.40495(6) 0.0177(3) Uani 1 1 d . . . . . H17A H 0.651600 0.410983 0.428203 0.021 Uiso 1 1 calc R U . . . H17B H 0.786295 0.299683 0.430860 0.021 Uiso 1 1 calc R U . . . C18 C 0.93914(14) 0.53560(14) 0.41129(5) 0.0141(2) Uani 1 1 d . . . . . C19 C 1.02498(15) 0.57525(15) 0.51268(6) 0.0169(2) Uani 1 1 d . . . . . C20 C 1.0359(2) 0.73235(16) 0.50696(7) 0.0266(3) Uani 1 1 d . . . . . H20A H 1.082039 0.756059 0.468961 0.040 Uiso 1 1 calc R U . . . H20B H 1.097524 0.769193 0.539210 0.040 Uiso 1 1 calc R U . . . H20C H 0.935102 0.772759 0.509027 0.040 Uiso 1 1 calc R U . . . C21 C 1.17613(17) 0.50381(18) 0.50480(7) 0.0240(3) Uani 1 1 d . . . . . H21A H 1.162402 0.403174 0.506684 0.036 Uiso 1 1 calc R U . . . H21B H 1.244547 0.533252 0.536304 0.036 Uiso 1 1 calc R U . . . H21C H 1.218681 0.529046 0.466330 0.036 Uiso 1 1 calc R U . . . C22 C 0.95410(19) 0.53503(18) 0.57149(6) 0.0249(3) Uani 1 1 d . . . . . H22A H 0.854307 0.577128 0.574617 0.037 Uiso 1 1 calc R U . . . H22B H 1.017454 0.568100 0.603975 0.037 Uiso 1 1 calc R U . . . H22C H 0.944937 0.433994 0.573733 0.037 Uiso 1 1 calc R U . . . N1 N 0.83460(12) 0.46793(12) 0.37910(5) 0.0134(2) Uani 1 1 d . . . . . O1 O 0.91737(11) 0.51743(12) 0.46954(4) 0.0179(2) Uani 1 1 d . . . . . O2 O 0.84294(11) 0.70218(10) 0.30519(4) 0.01399(18) Uani 1 1 d . . . . . H2A H 0.920970 0.687292 0.325039 0.021 Uiso 1 1 calc R U . . . O3 O 1.04010(11) 0.60660(11) 0.38948(4) 0.0166(2) Uani 1 1 d . . . . . 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 C1 0.0128(5) 0.0138(5) 0.0135(5) 0.0001(4) -0.0008(4) -0.0006(4) C2 0.0139(6) 0.0173(6) 0.0183(6) 0.0026(5) -0.0023(4) -0.0027(5) C3 0.0110(5) 0.0190(6) 0.0241(6) 0.0043(5) 0.0029(5) 0.0000(4) C4 0.0158(6) 0.0191(6) 0.0201(6) 0.0008(5) 0.0062(5) 0.0019(5) C5 0.0155(6) 0.0146(5) 0.0139(5) -0.0011(4) 0.0021(4) 0.0006(5) C6 0.0106(5) 0.0115(5) 0.0119(5) 0.0012(4) 0.0004(4) 0.0002(4) C7 0.0106(5) 0.0105(5) 0.0102(5) -0.0006(4) 0.0005(4) -0.0005(4) C8 0.0107(5) 0.0118(5) 0.0116(5) -0.0002(4) 0.0002(4) -0.0017(4) C9 0.0174(6) 0.0142(5) 0.0154(5) 0.0002(4) 0.0022(4) 0.0016(5) C10 0.0222(6) 0.0203(6) 0.0167(6) -0.0039(5) 0.0054(5) 0.0012(5) C11 0.0228(6) 0.0261(7) 0.0124(5) 0.0002(5) 0.0043(5) -0.0046(6) C12 0.0213(6) 0.0211(6) 0.0154(6) 0.0055(5) -0.0002(5) -0.0020(5) C13 0.0151(5) 0.0157(6) 0.0154(6) 0.0021(4) 0.0010(4) 0.0007(5) C14 0.0114(5) 0.0117(5) 0.0107(5) 0.0005(4) 0.0001(4) -0.0005(4) C15 0.0168(5) 0.0112(5) 0.0164(5) 0.0002(4) -0.0022(4) -0.0020(4) C16 0.0183(6) 0.0162(6) 0.0194(6) 0.0037(5) -0.0014(5) -0.0064(5) C17 0.0180(6) 0.0193(6) 0.0159(6) 0.0044(5) 0.0004(5) -0.0062(5) C18 0.0129(5) 0.0180(6) 0.0113(5) 0.0003(4) -0.0011(4) 0.0005(4) C19 0.0192(6) 0.0208(6) 0.0108(5) -0.0005(5) -0.0033(5) -0.0015(5) C20 0.0426(9) 0.0199(7) 0.0172(6) -0.0018(5) -0.0011(6) -0.0010(7) C21 0.0197(6) 0.0311(8) 0.0211(6) 0.0008(6) -0.0067(5) 0.0029(6) C22 0.0301(7) 0.0323(8) 0.0124(6) 0.0011(5) -0.0006(5) -0.0034(6) N1 0.0137(4) 0.0161(5) 0.0104(4) 0.0021(4) -0.0001(4) -0.0033(4) O1 0.0161(4) 0.0273(5) 0.0104(4) 0.0012(4) -0.0019(3) -0.0046(4) O2 0.0151(4) 0.0108(4) 0.0160(4) -0.0023(3) -0.0031(3) -0.0022(3) O3 0.0133(4) 0.0236(5) 0.0130(4) 0.0004(3) -0.0007(3) -0.0053(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' 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 C2 C1 C6 120.57(12) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 120.05(13) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.00(12) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.79(13) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.60(12) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 118.97(11) . . ? C5 C6 C7 119.85(11) . . ? C1 C6 C7 120.95(11) . . ? O2 C7 C6 107.35(10) . . ? O2 C7 C8 107.05(9) . . ? C6 C7 C8 111.14(10) . . ? O2 C7 C14 108.99(9) . . ? C6 C7 C14 110.20(10) . . ? C8 C7 C14 111.94(10) . . ? C9 C8 C13 118.46(11) . . ? C9 C8 C7 124.41(11) . . ? C13 C8 C7 117.08(11) . . ? C8 C9 C10 120.49(12) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.48(13) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.50(12) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.00(13) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 121.05(12) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? N1 C14 C15 102.75(10) . . ? N1 C14 C7 112.19(10) . . ? C15 C14 C7 115.97(10) . . ? N1 C14 H14 108.5 . . ? C15 C14 H14 108.5 . . ? C7 C14 H14 108.5 . . ? C14 C15 C16 105.32(10) . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15B 110.7 . . ? C16 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? C17 C16 C15 104.38(11) . . ? C17 C16 H16A 110.9 . . ? C15 C16 H16A 110.9 . . ? C17 C16 H16B 110.9 . . ? C15 C16 H16B 110.9 . . ? H16A C16 H16B 108.9 . . ? N1 C17 C16 103.93(10) . . ? N1 C17 H17A 111.0 . . ? C16 C17 H17A 111.0 . . ? N1 C17 H17B 111.0 . . ? C16 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? O3 C18 O1 124.75(12) . . ? O3 C18 N1 123.76(12) . . ? O1 C18 N1 111.48(11) . . ? O1 C19 C22 102.23(11) . . ? O1 C19 C21 108.98(11) . . ? C22 C19 C21 110.69(12) . . ? O1 C19 C20 111.16(12) . . ? C22 C19 C20 110.73(13) . . ? C21 C19 C20 112.58(13) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 N1 C17 122.79(11) . . ? C18 N1 C14 119.44(10) . . ? C17 N1 C14 113.52(10) . . ? C18 O1 C19 120.33(10) . . ? C7 O2 H2A 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3925(18) . ? C1 C6 1.4000(17) . ? C1 H1 0.9500 . ? C2 C3 1.3909(19) . ? C2 H2 0.9500 . ? C3 C4 1.394(2) . ? C3 H3 0.9500 . ? C4 C5 1.3986(18) . ? C4 H4 0.9500 . ? C5 C6 1.3947(17) . ? C5 H5 0.9500 . ? C6 C7 1.5245(16) . ? C7 O2 1.4362(14) . ? C7 C8 1.5357(16) . ? C7 C14 1.5625(17) . ? C8 C9 1.3938(18) . ? C8 C13 1.4006(17) . ? C9 C10 1.4002(18) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.393(2) . ? C11 H11 0.9500 . ? C12 C13 1.3912(18) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N1 1.4774(15) . ? C14 C15 1.5365(17) . ? C14 H14 1.0000 . ? C15 C16 1.5383(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.531(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N1 1.4731(17) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O3 1.2337(16) . ? C18 O1 1.3436(15) . ? C18 N1 1.3506(16) . ? C19 O1 1.4775(16) . ? C19 C22 1.5232(19) . ? C19 C21 1.523(2) . ? C19 C20 1.525(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O2 H2A 0.8400 . ? 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 _geom_hbond_publ_flag C20 H20A O3 0.98 2.34 2.9222(18) 117.6 . yes C21 H21C O3 0.98 2.47 3.0430(18) 116.8 . yes O2 H2A O3 0.84 1.96 2.7519(14) 155.8 . yes 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 C6 C1 C2 C3 0.7(2) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C1 1.50(19) . . . . ? C4 C5 C6 C7 -173.05(12) . . . . ? C2 C1 C6 C5 -1.72(19) . . . . ? C2 C1 C6 C7 172.77(12) . . . . ? C5 C6 C7 O2 -33.32(15) . . . . ? C1 C6 C7 O2 152.24(11) . . . . ? C5 C6 C7 C8 -150.07(11) . . . . ? C1 C6 C7 C8 35.49(16) . . . . ? C5 C6 C7 C14 85.25(14) . . . . ? C1 C6 C7 C14 -89.20(13) . . . . ? O2 C7 C8 C9 120.76(13) . . . . ? C6 C7 C8 C9 -122.31(13) . . . . ? C14 C7 C8 C9 1.39(17) . . . . ? O2 C7 C8 C13 -56.82(14) . . . . ? C6 C7 C8 C13 60.11(14) . . . . ? C14 C7 C8 C13 -176.19(11) . . . . ? C13 C8 C9 C10 -0.3(2) . . . . ? C7 C8 C9 C10 -177.88(12) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C11 C12 C13 C8 0.6(2) . . . . ? C9 C8 C13 C12 -0.1(2) . . . . ? C7 C8 C13 C12 177.58(12) . . . . ? O2 C7 C14 N1 47.76(13) . . . . ? C6 C7 C14 N1 -69.80(12) . . . . ? C8 C7 C14 N1 165.98(10) . . . . ? O2 C7 C14 C15 165.39(10) . . . . ? C6 C7 C14 C15 47.83(14) . . . . ? C8 C7 C14 C15 -76.39(13) . . . . ? N1 C14 C15 C16 26.49(12) . . . . ? C7 C14 C15 C16 -96.26(12) . . . . ? C14 C15 C16 C17 -32.47(13) . . . . ? C15 C16 C17 N1 25.05(14) . . . . ? O3 C18 N1 C17 169.16(13) . . . . ? O1 C18 N1 C17 -11.85(18) . . . . ? O3 C18 N1 C14 13.9(2) . . . . ? O1 C18 N1 C14 -167.17(11) . . . . ? C16 C17 N1 C18 -165.46(12) . . . . ? C16 C17 N1 C14 -8.83(15) . . . . ? C15 C14 N1 C18 146.38(12) . . . . ? C7 C14 N1 C18 -88.37(14) . . . . ? C15 C14 N1 C17 -11.10(14) . . . . ? C7 C14 N1 C17 114.15(12) . . . . ? O3 C18 O1 C19 -5.0(2) . . . . ? N1 C18 O1 C19 176.06(12) . . . . ? C22 C19 O1 C18 178.02(12) . . . . ? C21 C19 O1 C18 -64.80(16) . . . . ? C20 C19 O1 C18 59.84(17) . . . . ?