#------------------------------------------------------------------------------ #$Date: 2026-06-28 02:04:10 +0100 (Sun, 28 Jun 2026) $ #$Revision: 306672 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/44/7064461.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_7064461 loop_ _publ_author_name 'Vos, Cyler W.' 'Croke, Rylan' 'Lin, Jian-Bin' 'Kozak, Christopher M.' _publ_section_title ; Ring-Opening Polymerization of Lactide and Ring-Opening Copolymerization of Cyclohexene Oxide and Phthalic Anhydride by Multinuclear Complexes of Zinc, Magnesium and Potassium ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ01550F _journal_year 2026 _chemical_formula_moiety 'C22 H32 N2 O4' _chemical_formula_sum 'C22 H32 N2 O4' _chemical_formula_weight 388.49 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2024-04-30 _audit_creation_method ; Olex2 1.5-ac6-016 (compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897) ; _audit_update_record ; 2025-07-29 deposited with the CCDC. 2026-06-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.1140(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.64430(10) _cell_length_b 14.5605(2) _cell_length_c 14.6560(2) _cell_measurement_reflns_used 15053 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 78.7170 _cell_measurement_theta_min 4.3460 _cell_volume 2182.24(5) _computing_cell_refinement 'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.120a (release 16-04-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment air _diffrn_ambient_temperature 293(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.990 _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 -82.00 3.00 0.50 1.00 -- -47.13 105.00-114.00 170 2 \w 18.00 84.00 0.50 1.00 -- 47.13-105.00 145.00 132 3 \w -163.00 -83.00 0.50 2.00 -- -91.75-105.00 145.00 160 4 \w -81.00 -21.00 0.50 2.00 -- -91.75 105.00-114.00 120 5 \w 42.00 107.00 0.50 2.00 -- 113.25-105.00 145.00 130 6 \w 105.00 178.00 0.50 2.00 -- 113.25 105.00-114.00 146 7 \w -16.00 28.00 0.50 1.00 -- -47.13 19.00 -90.00 88 8 \w -16.00 28.00 0.50 1.00 -- -47.13 19.00 30.00 88 9 \w -16.00 28.00 0.50 1.00 -- -47.13 19.00 -30.00 88 10 \w -34.00 27.00 0.50 1.00 -- -47.13 37.00 0.00 122 11 \w -16.00 28.00 0.50 1.00 -- -47.13 19.00 60.00 88 12 \w -28.00 30.00 0.50 1.00 -- 47.13 -19.00 60.00 116 13 \w -164.00 -83.00 0.50 2.00 -- -91.75 -94.00 -90.00 162 14 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00-150.00 76 15 \w 96.00 178.00 0.50 2.00 -- 113.25 61.00 -60.00 164 16 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 30.00 76 17 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 60.00 76 18 \w 43.00 111.00 0.50 2.00 -- 113.25-125.00 -30.00 136 19 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 0.00 76 20 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 -60.00 76 21 \w 41.00 106.00 0.50 2.00 -- 113.25 -94.00-150.00 130 22 \w 96.00 178.00 0.50 2.00 -- 113.25 15.00 60.00 164 23 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00-180.00 76 24 \w 99.00 178.00 0.50 2.00 -- 113.25 30.00-150.00 158 25 \w 99.00 178.00 0.50 2.00 -- 113.25 30.00-150.00 158 26 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00-120.00 76 27 \w 41.00 106.00 0.50 2.00 -- 113.25 -94.00 150.00 130 28 \w 43.00 111.00 0.50 2.00 -- 113.25-125.00-120.00 136 29 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 120.00 76 30 \w 41.00 106.00 0.50 2.00 -- 113.25 -94.00-180.00 130 31 \w 41.00 106.00 0.50 2.00 -- 113.25 -94.00 -30.00 130 32 \w 41.00 79.00 0.50 2.00 -- 113.25 -61.00 -30.00 76 33 \w 24.00 70.00 0.50 1.00 -- 47.13 77.00 -30.00 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0555891000 _diffrn_orient_matrix_UB_12 -0.0980185000 _diffrn_orient_matrix_UB_13 -0.0190354000 _diffrn_orient_matrix_UB_21 0.1190935000 _diffrn_orient_matrix_UB_22 -0.0286451000 _diffrn_orient_matrix_UB_23 -0.0337182000 _diffrn_orient_matrix_UB_31 0.0736365000 _diffrn_orient_matrix_UB_32 -0.0276744000 _diffrn_orient_matrix_UB_33 0.1023419000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0190 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 28114 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.559 _diffrn_reflns_theta_min 4.368 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024) 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 1.182 _exptl_crystal_description prism _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.097 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.165 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 4683 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0419 _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^)+(0.0651P)^2^+0.2470P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1191 _refine_ls_wR_factor_ref 0.1248 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3872 _reflns_number_total 4683 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj01550f2.cif _cod_data_source_block cv-306ligand _cod_database_code 7064461 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C22H32N2O4 _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 0.962 _shelx_estimated_absorpt_t_min 0.886 _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: C7(H7A,H7B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,H20B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3A), C5(H5), C12(H12), C14(H14) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C) ; _shelx_res_file ; TITL cv-306ligand_a.res in P2(1)/n cv-306ligand.res created by SHELXL-2018/3 at 08:22:38 on 30-Apr-2024 REM Old TITL CV-306 Ligand in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.173, Rweak 0.039, Alpha 0.025 REM 0.347 for 196 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N2 O3 CELL 1.54184 10.6443 14.5605 14.656 90 106.114 90 ZERR 4 0.0001 0.0002 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 88 128 8 16 L.S. 8 PLAN 1 SIZE 0.06 0.097 0.19 TEMP 20(2) HTAB O3 N1 HTAB O1 N2 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.065100 0.247000 FVAR 0.58028 O1 4 1.044426 0.288041 0.372982 11.00000 0.07569 0.04949 = 0.04627 0.00144 0.00333 -0.00265 H1 2 1.008967 0.233648 0.345758 11.00000 0.08888 O2 4 1.123714 0.447028 0.450234 11.00000 0.08030 0.05272 = 0.04522 -0.00678 -0.00200 0.00266 O3 4 0.725076 0.333713 0.320529 11.00000 0.04517 0.07879 = 0.04769 -0.01331 0.00372 0.00375 H3 2 0.780621 0.307021 0.296753 11.00000 0.08081 O4 4 0.517069 0.360253 0.379252 11.00000 0.05762 0.09964 = 0.04717 -0.00798 0.01353 0.01328 N1 3 0.822807 0.235708 0.188670 11.00000 0.04331 0.04492 = 0.04354 -0.00469 0.00699 0.00164 N2 3 0.949088 0.105881 0.331201 11.00000 0.08292 0.04575 = 0.06045 -0.00032 -0.00140 0.00151 C1 1 1.038763 0.360051 0.312647 11.00000 0.04246 0.04858 = 0.04547 -0.00117 0.00733 0.00245 C2 1 1.081124 0.445930 0.353490 11.00000 0.04705 0.05119 = 0.04589 -0.00449 0.00478 0.00404 C3 1 1.079818 0.521716 0.296352 11.00000 0.05975 0.04890 = 0.05843 -0.00467 0.00997 -0.00040 AFIX 43 H3A 2 1.107678 0.578219 0.324275 11.00000 -1.20000 AFIX 0 C4 1 1.037497 0.514935 0.197665 11.00000 0.06546 0.05479 = 0.05588 0.00342 0.01636 0.00279 C5 1 0.995166 0.430467 0.158454 11.00000 0.05698 0.06200 = 0.04299 -0.00127 0.01280 0.00273 AFIX 43 H5 2 0.965871 0.425102 0.092712 11.00000 -1.20000 AFIX 0 C6 1 0.994834 0.352830 0.214117 11.00000 0.03981 0.05224 = 0.04524 -0.00451 0.01080 0.00216 C7 1 0.946094 0.262178 0.169032 11.00000 0.04653 0.05532 = 0.04540 -0.00874 0.01213 0.00228 AFIX 23 H7A 2 0.932548 0.266360 0.100927 11.00000 -1.20000 H7B 2 1.011513 0.215261 0.193369 11.00000 -1.20000 AFIX 0 C8 1 1.160365 0.533493 0.495205 11.00000 0.10237 0.05633 = 0.05821 -0.01359 -0.00481 0.00666 AFIX 137 H8A 2 1.090106 0.576502 0.473198 11.00000 -1.50000 H8B 2 1.236959 0.555852 0.479969 11.00000 -1.50000 H8C 2 1.178734 0.526400 0.562756 11.00000 -1.50000 AFIX 0 C9 1 1.037778 0.598059 0.136306 11.00000 0.12618 0.06436 = 0.07028 0.01028 0.02666 -0.00388 AFIX 137 H9A 2 1.124715 0.622688 0.150338 11.00000 -1.50000 H9B 2 0.979754 0.643746 0.148926 11.00000 -1.50000 H9C 2 1.009043 0.580648 0.070603 11.00000 -1.50000 AFIX 0 C10 1 0.606149 0.317460 0.257188 11.00000 0.04270 0.04640 = 0.04397 -0.00053 0.00529 0.00278 C11 1 0.494192 0.331175 0.287208 11.00000 0.05068 0.05267 = 0.04413 0.00212 0.01009 0.00612 C12 1 0.371958 0.315648 0.225024 11.00000 0.04331 0.06180 = 0.05492 0.00504 0.01260 0.00650 AFIX 43 H12 2 0.297515 0.326022 0.244980 11.00000 -1.20000 AFIX 0 C13 1 0.358998 0.284597 0.132677 11.00000 0.04328 0.05442 = 0.05360 0.00241 0.00367 0.00152 C14 1 0.470320 0.272595 0.103590 11.00000 0.04684 0.04949 = 0.04349 -0.00035 0.00371 0.00197 AFIX 43 H14 2 0.462635 0.251926 0.042240 11.00000 -1.20000 AFIX 0 C15 1 0.594391 0.290705 0.163966 11.00000 0.04370 0.04337 = 0.04361 0.00068 0.00709 0.00320 C16 1 0.713726 0.289358 0.128024 11.00000 0.04522 0.05591 = 0.04152 0.00120 0.00751 0.00210 AFIX 23 H16A 2 0.690277 0.263658 0.064469 11.00000 -1.20000 H16B 2 0.742770 0.351980 0.123923 11.00000 -1.20000 AFIX 0 C17 1 0.407475 0.379743 0.412286 11.00000 0.07352 0.12604 = 0.06431 -0.01259 0.02918 0.01342 AFIX 137 H17A 2 0.356726 0.427676 0.374326 11.00000 -1.50000 H17B 2 0.436335 0.399298 0.477328 11.00000 -1.50000 H17C 2 0.354770 0.325520 0.407688 11.00000 -1.50000 AFIX 0 C18 1 0.225269 0.265838 0.066626 11.00000 0.04453 0.09808 = 0.07190 -0.01082 0.00298 0.00147 AFIX 137 H18A 2 0.233872 0.244586 0.006645 11.00000 -1.50000 H18B 2 0.174473 0.321277 0.057271 11.00000 -1.50000 H18C 2 0.182311 0.219705 0.093904 11.00000 -1.50000 AFIX 0 C19 1 0.794948 0.137428 0.173596 11.00000 0.06235 0.04756 = 0.05440 -0.00948 0.00520 -0.00294 AFIX 23 H19A 2 0.782770 0.123432 0.106994 11.00000 -1.20000 H19B 2 0.713544 0.123818 0.188354 11.00000 -1.20000 AFIX 0 C20 1 0.901184 0.075644 0.232822 11.00000 0.07527 0.04590 = 0.06637 -0.00705 0.00958 0.00442 AFIX 23 H20A 2 0.867201 0.013702 0.231556 11.00000 -1.20000 H20B 2 0.973635 0.074041 0.204737 11.00000 -1.20000 AFIX 0 C21 1 1.064016 0.053394 0.380633 11.00000 0.11392 0.06957 = 0.10541 0.00902 -0.02975 0.01297 AFIX 137 H21A 2 1.095418 0.074869 0.444887 11.00000 -1.50000 H21B 2 1.131068 0.061088 0.348946 11.00000 -1.50000 H21C 2 1.041454 -0.010436 0.380706 11.00000 -1.50000 AFIX 0 C22 1 0.846146 0.095100 0.379644 11.00000 0.13466 0.07659 = 0.07226 -0.00429 0.03513 -0.01957 AFIX 137 H22A 2 0.774473 0.135252 0.351110 11.00000 -1.50000 H22B 2 0.880657 0.110368 0.445597 11.00000 -1.50000 H22C 2 0.816084 0.032641 0.373857 11.00000 -1.50000 AFIX 0 HKLF 4 REM cv-306ligand_a.res in P2(1)/n REM wR2 = 0.1248, GooF = S = 1.077, Restrained GooF = 1.077 for all data REM R1 = 0.0419 for 3872 Fo > 4sig(Fo) and 0.0490 for all 4683 data REM 267 parameters refined using 0 restraints END WGHT 0.0651 0.2471 REM Highest difference peak 0.165, deepest hole -0.181, 1-sigma level 0.035 Q1 1 1.0796 0.0605 0.2575 11.00000 0.05 0.16 ; _shelx_res_checksum 24056 _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 1.368 _oxdiff_exptl_absorpt_empirical_full_min 0.771 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, 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 O1 O 1.04443(11) 0.28804(7) 0.37298(6) 0.0599(3) Uani 1 1 d . . . . . H1 H 1.009(2) 0.2336(15) 0.3458(14) 0.089(6) Uiso 1 1 d . . . . . O2 O 1.12371(11) 0.44703(7) 0.45023(7) 0.0633(3) Uani 1 1 d . . . . . O3 O 0.72508(10) 0.33371(8) 0.32053(7) 0.0591(3) Uani 1 1 d . . . . . H3 H 0.781(2) 0.3070(14) 0.2968(14) 0.081(6) Uiso 1 1 d . . . . . O4 O 0.51707(10) 0.36025(9) 0.37925(7) 0.0683(3) Uani 1 1 d . . . . . N1 N 0.82281(10) 0.23571(7) 0.18867(7) 0.0449(2) Uani 1 1 d . . . . . N2 N 0.94909(15) 0.10588(8) 0.33120(9) 0.0673(3) Uani 1 1 d . . . . . C1 C 1.03876(12) 0.36005(8) 0.31265(8) 0.0465(3) Uani 1 1 d . . . . . C2 C 1.08112(13) 0.44593(9) 0.35349(9) 0.0497(3) Uani 1 1 d . . . . . C3 C 1.07982(15) 0.52172(10) 0.29635(10) 0.0570(3) Uani 1 1 d . . . . . H3A H 1.107678 0.578219 0.324275 0.068 Uiso 1 1 calc R U . . . C4 C 1.03750(15) 0.51493(10) 0.19766(10) 0.0588(3) Uani 1 1 d . . . . . C5 C 0.99517(14) 0.43047(10) 0.15845(9) 0.0542(3) Uani 1 1 d . . . . . H5 H 0.965871 0.425102 0.092712 0.065 Uiso 1 1 calc R U . . . C6 C 0.99483(11) 0.35283(9) 0.21412(8) 0.0460(3) Uani 1 1 d . . . . . C7 C 0.94609(12) 0.26218(9) 0.16903(9) 0.0492(3) Uani 1 1 d . . . . . H7A H 0.932548 0.266360 0.100927 0.059 Uiso 1 1 calc R U . . . H7B H 1.011513 0.215261 0.193369 0.059 Uiso 1 1 calc R U . . . C8 C 1.1604(2) 0.53349(11) 0.49520(12) 0.0777(5) Uani 1 1 d . . . . . H8A H 1.090106 0.576502 0.473198 0.117 Uiso 1 1 calc R U . . . H8B H 1.236959 0.555852 0.479969 0.117 Uiso 1 1 calc R U . . . H8C H 1.178734 0.526400 0.562756 0.117 Uiso 1 1 calc R U . . . C9 C 1.0378(2) 0.59806(13) 0.13631(13) 0.0871(6) Uani 1 1 d . . . . . H9A H 1.124715 0.622688 0.150338 0.131 Uiso 1 1 calc R U . . . H9B H 0.979754 0.643746 0.148926 0.131 Uiso 1 1 calc R U . . . H9C H 1.009043 0.580648 0.070603 0.131 Uiso 1 1 calc R U . . . C10 C 0.60615(12) 0.31746(8) 0.25719(8) 0.0457(3) Uani 1 1 d . . . . . C11 C 0.49419(13) 0.33118(9) 0.28721(9) 0.0498(3) Uani 1 1 d . . . . . C12 C 0.37196(13) 0.31565(10) 0.22502(9) 0.0535(3) Uani 1 1 d . . . . . H12 H 0.297515 0.326022 0.244980 0.064 Uiso 1 1 calc R U . . . C13 C 0.35900(12) 0.28460(10) 0.13268(9) 0.0524(3) Uani 1 1 d . . . . . C14 C 0.47032(12) 0.27260(9) 0.10359(9) 0.0484(3) Uani 1 1 d . . . . . H14 H 0.462635 0.251926 0.042240 0.058 Uiso 1 1 calc R U . . . C15 C 0.59439(12) 0.29070(8) 0.16397(8) 0.0446(3) Uani 1 1 d . . . . . C16 C 0.71373(12) 0.28936(9) 0.12802(8) 0.0485(3) Uani 1 1 d . . . . . H16A H 0.690277 0.263658 0.064469 0.058 Uiso 1 1 calc R U . . . H16B H 0.742770 0.351980 0.123923 0.058 Uiso 1 1 calc R U . . . C17 C 0.40748(19) 0.37974(17) 0.41229(13) 0.0859(6) Uani 1 1 d . . . . . H17A H 0.356726 0.427676 0.374326 0.129 Uiso 1 1 calc R U . . . H17B H 0.436335 0.399298 0.477328 0.129 Uiso 1 1 calc R U . . . H17C H 0.354770 0.325520 0.407688 0.129 Uiso 1 1 calc R U . . . C18 C 0.22527(15) 0.26584(14) 0.06663(12) 0.0741(5) Uani 1 1 d . . . . . H18A H 0.233872 0.244586 0.006645 0.111 Uiso 1 1 calc R U . . . H18B H 0.174473 0.321277 0.057271 0.111 Uiso 1 1 calc R U . . . H18C H 0.182311 0.219705 0.093904 0.111 Uiso 1 1 calc R U . . . C19 C 0.79495(15) 0.13743(9) 0.17360(10) 0.0570(3) Uani 1 1 d . . . . . H19A H 0.782770 0.123432 0.106994 0.068 Uiso 1 1 calc R U . . . H19B H 0.713544 0.123818 0.188354 0.068 Uiso 1 1 calc R U . . . C20 C 0.90118(17) 0.07564(10) 0.23282(11) 0.0645(4) Uani 1 1 d . . . . . H20A H 0.867201 0.013702 0.231556 0.077 Uiso 1 1 calc R U . . . H20B H 0.973635 0.074041 0.204737 0.077 Uiso 1 1 calc R U . . . C21 C 1.0640(3) 0.05339(14) 0.38063(17) 0.1084(8) Uani 1 1 d . . . . . H21A H 1.095418 0.074869 0.444887 0.163 Uiso 1 1 calc R U . . . H21B H 1.131068 0.061088 0.348946 0.163 Uiso 1 1 calc R U . . . H21C H 1.041454 -0.010436 0.380706 0.163 Uiso 1 1 calc R U . . . C22 C 0.8461(3) 0.09510(14) 0.37964(14) 0.0932(6) Uani 1 1 d . . . . . H22A H 0.774473 0.135252 0.351110 0.140 Uiso 1 1 calc R U . . . H22B H 0.880657 0.110368 0.445597 0.140 Uiso 1 1 calc R U . . . H22C H 0.816084 0.032641 0.373857 0.140 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0757(7) 0.0495(5) 0.0463(5) 0.0014(4) 0.0033(4) -0.0027(5) O2 0.0803(7) 0.0527(5) 0.0452(5) -0.0068(4) -0.0020(4) 0.0027(5) O3 0.0452(5) 0.0788(7) 0.0477(5) -0.0133(4) 0.0037(4) 0.0037(5) O4 0.0576(6) 0.0996(8) 0.0472(5) -0.0080(5) 0.0135(4) 0.0133(5) N1 0.0433(5) 0.0449(5) 0.0435(5) -0.0047(4) 0.0070(4) 0.0016(4) N2 0.0829(9) 0.0457(6) 0.0604(7) -0.0003(5) -0.0014(6) 0.0015(6) C1 0.0425(6) 0.0486(6) 0.0455(6) -0.0012(5) 0.0073(5) 0.0025(5) C2 0.0471(6) 0.0512(7) 0.0459(6) -0.0045(5) 0.0048(5) 0.0040(5) C3 0.0597(8) 0.0489(7) 0.0584(7) -0.0047(6) 0.0100(6) -0.0004(6) C4 0.0655(8) 0.0548(8) 0.0559(7) 0.0034(6) 0.0164(6) 0.0028(6) C5 0.0570(7) 0.0620(8) 0.0430(6) -0.0013(5) 0.0128(5) 0.0027(6) C6 0.0398(6) 0.0522(7) 0.0452(6) -0.0045(5) 0.0108(5) 0.0022(5) C7 0.0465(6) 0.0553(7) 0.0454(6) -0.0087(5) 0.0121(5) 0.0023(5) C8 0.1024(13) 0.0563(8) 0.0582(8) -0.0136(7) -0.0048(8) 0.0067(8) C9 0.1262(17) 0.0644(10) 0.0703(10) 0.0103(8) 0.0267(11) -0.0039(10) C10 0.0427(6) 0.0464(6) 0.0440(6) -0.0005(5) 0.0053(5) 0.0028(5) C11 0.0507(7) 0.0527(7) 0.0441(6) 0.0021(5) 0.0101(5) 0.0061(5) C12 0.0433(6) 0.0618(8) 0.0549(7) 0.0050(6) 0.0126(5) 0.0065(6) C13 0.0433(6) 0.0544(7) 0.0536(7) 0.0024(5) 0.0037(5) 0.0015(5) C14 0.0468(7) 0.0495(6) 0.0435(6) -0.0004(5) 0.0037(5) 0.0020(5) C15 0.0437(6) 0.0434(6) 0.0436(6) 0.0007(4) 0.0071(5) 0.0032(5) C16 0.0452(6) 0.0559(7) 0.0415(6) 0.0012(5) 0.0075(5) 0.0021(5) C17 0.0735(11) 0.1260(16) 0.0643(9) -0.0126(10) 0.0292(8) 0.0134(11) C18 0.0445(8) 0.0981(13) 0.0719(9) -0.0108(9) 0.0030(7) 0.0015(8) C19 0.0624(8) 0.0476(7) 0.0544(7) -0.0095(5) 0.0052(6) -0.0029(6) C20 0.0753(10) 0.0459(7) 0.0664(9) -0.0070(6) 0.0096(7) 0.0044(6) C21 0.1139(17) 0.0696(11) 0.1054(16) 0.0090(10) -0.0298(13) 0.0130(11) C22 0.1347(19) 0.0766(12) 0.0723(11) -0.0043(9) 0.0351(12) -0.0196(12) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 1 -2 0.0926 1 -1 1 0.0342 -5 3 8 0.0477 4 -2 -8 0.0275 -7 1 5 0.0429 7 -1 -5 0.0149 6 -2 3 0.0317 -4 -3 -6 0.0585 3 2 7 0.0275 1 9 -2 0.0817 -2 -9 0 0.1028 -1 -3 -8 0.0522 -1 9 0 0.0836 -7 -1 2 0.0479 -1 3 -8 0.0788 4 6 -6 0.0575 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 C1 O1 H1 116.3(13) . . ? C2 O2 C8 117.44(11) . . ? C10 O3 H3 105.0(13) . . ? C11 O4 C17 117.54(12) . . ? C7 N1 C16 109.83(10) . . ? C19 N1 C7 112.37(10) . . ? C19 N1 C16 109.50(10) . . ? C20 N2 C22 110.03(14) . . ? C21 N2 C20 110.43(15) . . ? C21 N2 C22 109.88(18) . . ? O1 C1 C2 117.21(11) . . ? O1 C1 C6 123.82(11) . . ? C6 C1 C2 118.97(11) . . ? O2 C2 C1 115.34(11) . . ? O2 C2 C3 124.39(12) . . ? C3 C2 C1 120.26(12) . . ? C2 C3 H3A 119.4 . . ? C2 C3 C4 121.19(13) . . ? C4 C3 H3A 119.4 . . ? C3 C4 C9 120.55(14) . . ? C5 C4 C3 118.01(13) . . ? C5 C4 C9 121.44(14) . . ? C4 C5 H5 118.9 . . ? C4 C5 C6 122.18(12) . . ? C6 C5 H5 118.9 . . ? C1 C6 C5 119.38(12) . . ? C1 C6 C7 119.85(11) . . ? C5 C6 C7 120.76(11) . . ? N1 C7 C6 111.23(9) . . ? N1 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C6 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 C11 118.19(11) . . ? O3 C10 C15 121.93(11) . . ? C15 C10 C11 119.84(11) . . ? O4 C11 C10 114.90(11) . . ? O4 C11 C12 125.21(12) . . ? C12 C11 C10 119.88(12) . . ? C11 C12 H12 119.6 . . ? C11 C12 C13 120.85(12) . . ? C13 C12 H12 119.6 . . ? C12 C13 C18 120.16(13) . . ? C14 C13 C12 118.61(12) . . ? C14 C13 C18 121.22(13) . . ? C13 C14 H14 119.2 . . ? C13 C14 C15 121.59(12) . . ? C15 C14 H14 119.2 . . ? C10 C15 C14 119.11(12) . . ? C10 C15 C16 119.51(11) . . ? C14 C15 C16 121.19(11) . . ? N1 C16 C15 113.32(10) . . ? N1 C16 H16A 108.9 . . ? N1 C16 H16B 108.9 . . ? C15 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 108.8 . . ? N1 C19 H19B 108.8 . . ? N1 C19 C20 113.93(11) . . ? H19A C19 H19B 107.7 . . ? C20 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? N2 C20 C19 112.82(12) . . ? N2 C20 H20A 109.0 . . ? N2 C20 H20B 109.0 . . ? C19 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 O1 H1 0.92(2) . ? O1 C1 1.3621(15) . ? O2 C2 1.3636(15) . ? O2 C8 1.4244(18) . ? O3 H3 0.86(2) . ? O3 C10 1.3667(15) . ? O4 C11 1.3697(16) . ? O4 C17 1.4104(19) . ? N1 C7 1.4708(16) . ? N1 C16 1.4750(15) . ? N1 C19 1.4657(16) . ? N2 C20 1.458(2) . ? N2 C21 1.454(2) . ? N2 C22 1.470(3) . ? C1 C2 1.4055(17) . ? C1 C6 1.3929(16) . ? C2 C3 1.3830(19) . ? C3 H3A 0.9300 . ? C3 C4 1.394(2) . ? C4 C5 1.379(2) . ? C4 C9 1.508(2) . ? C5 H5 0.9300 . ? C5 C6 1.3946(19) . ? C6 C7 1.5026(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.3945(18) . ? C10 C15 1.3925(17) . ? C11 C12 1.3843(18) . ? C12 H12 0.9300 . ? C12 C13 1.3970(19) . ? C13 C14 1.3772(19) . ? C13 C18 1.5076(19) . ? C14 H14 0.9300 . ? C14 C15 1.3957(17) . ? C15 C16 1.5043(17) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C20 1.515(2) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O1 H1 N2 0.92(2) 1.96(2) 2.8451(16) 161.3(18) . yes O3 H3 N1 0.86(2) 2.05(2) 2.8230(14) 150.3(18) . 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 O1 C1 C2 O2 0.07(17) . . . . ? O1 C1 C2 C3 179.06(12) . . . . ? O1 C1 C6 C5 -178.80(12) . . . . ? O1 C1 C6 C7 2.00(18) . . . . ? O2 C2 C3 C4 178.56(13) . . . . ? O3 C10 C11 O4 0.07(18) . . . . ? O3 C10 C11 C12 179.85(12) . . . . ? O3 C10 C15 C14 178.16(12) . . . . ? O3 C10 C15 C16 -6.82(18) . . . . ? O4 C11 C12 C13 -179.01(13) . . . . ? N1 C19 C20 N2 44.40(19) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C1 C6 C7 N1 68.04(14) . . . . ? C2 C1 C6 C5 0.66(18) . . . . ? C2 C1 C6 C7 -178.54(11) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C2 C3 C4 C9 -179.46(16) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C1 -0.1(2) . . . . ? C4 C5 C6 C7 179.06(13) . . . . ? C5 C6 C7 N1 -111.15(13) . . . . ? C6 C1 C2 O2 -179.42(11) . . . . ? C6 C1 C2 C3 -0.43(19) . . . . ? C7 N1 C16 C15 -161.01(10) . . . . ? C7 N1 C19 C20 57.74(15) . . . . ? C8 O2 C2 C1 -176.37(13) . . . . ? C8 O2 C2 C3 4.7(2) . . . . ? C9 C4 C5 C6 179.69(15) . . . . ? C10 C11 C12 C13 1.2(2) . . . . ? C10 C15 C16 N1 53.14(15) . . . . ? C11 C10 C15 C14 -3.89(18) . . . . ? C11 C10 C15 C16 171.14(11) . . . . ? C11 C12 C13 C14 -2.1(2) . . . . ? C11 C12 C13 C18 178.52(14) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C10 3.02(19) . . . . ? C13 C14 C15 C16 -171.92(12) . . . . ? C14 C15 C16 N1 -131.94(12) . . . . ? C15 C10 C11 O4 -177.96(11) . . . . ? C15 C10 C11 C12 1.82(19) . . . . ? C16 N1 C7 C6 76.47(12) . . . . ? C16 N1 C19 C20 -179.93(12) . . . . ? C17 O4 C11 C10 176.90(15) . . . . ? C17 O4 C11 C12 -2.9(2) . . . . ? C18 C13 C14 C15 179.33(14) . . . . ? C19 N1 C7 C6 -161.38(10) . . . . ? C19 N1 C16 C15 75.15(13) . . . . ? C21 N2 C20 C19 -170.96(17) . . . . ? C22 N2 C20 C19 67.56(18) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1.0278 1.0020 -1.9746 -0.0035 -0.0845 -0.3055 1.0135 -1.0037 0.9785 0.0234 0.1165 0.2026 -4.9576 2.5431 7.7678 -0.1215 -0.9252 0.3595 4.4174 -2.0302 -8.4370 0.1140 0.8687 -0.4820 -6.5211 0.7889 5.4176 0.1820 -0.9819 0.0524 6.6014 -0.8977 -5.0805 -0.1823 0.9832 -0.0090 5.5664 -2.4774 2.7271 -0.1185 0.6419 0.7575 -3.5789 -2.8906 -5.9324 0.5952 -0.1434 -0.7907 3.2364 1.6481 6.6781 -0.4686 0.1131 0.8762 0.9480 9.1455 -2.2990 -0.9054 -0.0716 -0.4186 -1.6316 -9.1320 -0.3231 0.9920 0.0782 0.0995 -1.1848 -3.2302 -7.9916 0.5346 0.2209 -0.8157 -0.7601 9.3935 0.1751 -0.8818 -0.3655 -0.2980 -6.8397 -1.2753 2.2108 0.4631 -0.8526 -0.2421 -0.7892 2.6912 -8.3963 -0.0601 0.1120 -0.9919 4.4812 5.9272 -5.6565 -0.7224 0.5546 -0.4130