#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:22 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306472 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064383.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_7064383 loop_ _publ_author_name 'Gou, Yan' 'Wang, Jing' 'Li, Na' 'Hou, Shanling' 'Cheng, Yang' 'Li, Yuming' _publ_section_title ; DBU-mediated [3+2] annulation of 3-hydroxyisoindolinones with vinylsulfonium salts: an efficient approach to functionalized oxazolo[2,3-a]isoindolones ; _journal_issue 18 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7609 _journal_page_last 7613 _journal_paper_doi 10.1039/D6NJ00608F _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C22 H17 N O2' _chemical_formula_sum 'C22 H17 N O2' _chemical_formula_weight 327.36 _space_group_crystal_system monoclinic _space_group_IT_number 12 _space_group_name_Hall '-C 2y' _space_group_name_H-M_alt 'C 1 2/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2026-03-21 _audit_creation_method ; Olex2 1.5 (compiled 2026.03.20 svn.r2bc28608 for OlexSys, GUI svn.r7524) ; _audit_update_record ; 2026-03-24 deposited with the CCDC. 2026-04-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 128.825(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.236(3) _cell_length_b 9.0230(19) _cell_length_c 13.095(4) _cell_measurement_reflns_used 2055 _cell_measurement_temperature 293.00 _cell_measurement_theta_max 24.47 _cell_measurement_theta_min 2.24 _cell_volume 1678.6(7) _computing_cell_refinement 'SAINT V8.41 (Bruker, 2024)' _computing_data_collection 'APEX6 V2024.9-1 (Bruker, 2025)' _computing_data_reduction 'SAINT V8.41 (Bruker, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2025/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293.00 _diffrn_detector CPAD _diffrn_detector_area_resol_mean 7.41 _diffrn_detector_type 'Bruker PHOTON II' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE TXS PHOTON II' _diffrn_measurement_method '\w and \f shutterless scans' _diffrn_measurement_specimen_support 'nylon loop' _diffrn_radiation_monochromator 'Helios Multi-layer Optic' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.0422 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7182 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.439 _diffrn_reflns_theta_min 1.996 _diffrn_source 'Turbo X-Ray Source (TXS)' _diffrn_source_current 40.0 _diffrn_source_power 1.8 _diffrn_source_type 'Rotaing Anode' _diffrn_source_voltage 45.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1136 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.8964. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.295 _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.117 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.027 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 1833 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0533 _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^)+(0.0416P)^2^+0.8303P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1169 _refine_ls_wR_factor_ref 0.1344 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1263 _reflns_number_total 1833 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00608f2.cif _cod_data_source_block a _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas Adding full bibliography for 7064382--7064383.cif. ; _cod_original_sg_symbol_H-M C2/m _cod_database_code 7064383 _shelx_shelxl_version_number 2025/1 _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 0.993 _shelx_estimated_absorpt_t_min 0.989 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Fixed Sof: O1(0.5) O2(0.5) N1(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) H5(0.5) C4(0.5) H4(0.5) C3(0.5) H3(0.5) C2(0.5) C7(0.5) C8(0.5) C11(0.5) H11(0.5) C10(0.5) H10(0.5) C9(0.5) C14(0.5) H14(0.5) C13(0.5) H13(0.5) C12(0.5) H12(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16(0.5) C22(0.5) H22(0.5) C21(0.5) H21(0.5) C20(0.5) H20(0.5) C19(0.5) H19(0.5) C18(0.5) H18(0.5) C17(0.5) 3.a Ternary CH refined with riding coordinates: C16(H16) 3.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B) 3.c Aromatic/amide H refined with riding coordinates: C6(H6), C5(H5), C4(H4), C3(H3), C11(H11), C10(H10), C14(H14), C13(H13), C12(H12), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18) 3.d Fitted hexagon refined as free rotating group: C6(C5,C4,C3,C2,C7), C11(C10,C9,C14,C13,C12), C22(C21,C20,C19,C18,C17) ; _shelx_res_file ; TITL a_a.res in C2/m a.res created by SHELXL-2025/1 at 20:59:10 on 21-Mar-2026 REM Old TITL a_a.res in C2/m REM SHELXT solution in C2/m: R1 0.378, Rweak 0.076, Alpha 0.140 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N10 O3 CELL 0.71073 18.2357 9.023 13.0948 90 128.825 90 ZERR 4 0.0033 0.0019 0.0041 0 0.004 0 LATT 7 SYMM -X,+Y,-Z SFAC C H N O UNIT 88 68 4 8 L.S. 10 PLAN 5 SIZE 0.08 0.11 0.13 TEMP 19.85 CONF BOND LIST 6 MORE -1 BOND $H fmap 2 acta SIZE 0.08 0.11 0.13 REM REM REM WGHT 0.041600 0.830300 FVAR 1.09570 PART -1 O1 4 0.104490 0.444528 0.284601 10.50000 0.06206 0.05275 = 0.08362 -0.00250 0.05230 0.00896 O2 4 0.374590 0.319937 0.445114 10.50000 0.03836 0.05213 = 0.03504 -0.00676 0.02209 -0.00817 N1 3 0.220915 0.276130 0.346820 10.50000 0.03798 0.04206 = 0.04353 -0.00370 0.02621 -0.00016 C1 1 0.158954 0.389098 0.270794 10.50000 0.04083 0.03830 = 0.05243 -0.00796 0.02696 -0.00240 AFIX 66 C6 1 0.284277 0.376917 0.137926 10.50000 0.05099 0.05693 = 0.04392 -0.00153 0.02905 0.00195 AFIX 43 H6 2 0.337761 0.328476 0.160898 10.50000 -1.20000 AFIX 65 C5 1 0.234661 0.471341 0.030290 10.50000 0.06799 0.07323 = 0.04520 0.00413 0.03383 -0.00776 AFIX 43 H5 2 0.254948 0.486076 -0.018753 10.50000 -1.20000 AFIX 65 C4 1 0.154723 0.543742 -0.004045 10.50000 0.07082 0.05135 = 0.04317 0.00663 0.02670 0.00534 AFIX 43 H4 2 0.121526 0.606918 -0.076060 10.50000 -1.20000 AFIX 65 C3 1 0.124400 0.521719 0.069256 10.50000 0.04892 0.05621 = 0.05559 0.00778 0.02585 0.01155 AFIX 43 H3 2 0.070916 0.570160 0.046283 10.50000 -1.20000 AFIX 65 C2 1 0.174015 0.427295 0.176892 10.50000 0.03956 0.03988 = 0.04174 -0.00678 0.01994 -0.00287 C7 1 0.253954 0.354893 0.211228 10.50000 0.04253 0.04136 = 0.03776 -0.00582 0.02284 -0.00516 AFIX 0 C8 1 0.291371 0.259272 0.327689 10.50000 0.03584 0.04450 = 0.03573 -0.00689 0.02086 -0.00384 AFIX 66 C11 1 0.257863 -0.154795 0.257631 10.50000 0.09134 0.05303 = 0.06963 -0.01596 0.05372 -0.01185 AFIX 43 H11 2 0.212859 -0.227657 0.230143 10.50000 -1.20000 AFIX 65 C10 1 0.239923 -0.008855 0.269831 10.50000 0.05934 0.04847 = 0.04857 -0.01663 0.03467 -0.01618 AFIX 43 H10 2 0.182915 0.015927 0.250505 10.50000 -1.20000 AFIX 65 C9 1 0.307187 0.100045 0.310914 10.50000 0.04237 0.04766 = 0.03281 -0.00290 0.02146 0.00406 C14 1 0.392393 0.063006 0.339798 10.50000 0.04334 0.07502 = 0.04608 -0.01181 0.02382 0.00481 AFIX 43 H14 2 0.437397 0.135868 0.367286 10.50000 -1.20000 AFIX 65 C13 1 0.410334 -0.082933 0.327599 10.50000 0.06823 0.06886 = 0.06383 -0.00976 0.03820 0.01096 AFIX 43 H13 2 0.467342 -0.107714 0.346924 10.50000 -1.20000 AFIX 65 C12 1 0.343071 -0.191835 0.286515 10.50000 0.10559 0.05222 = 0.06539 -0.00335 0.05228 0.02286 AFIX 43 H12 2 0.355075 -0.289478 0.278353 10.50000 -1.20000 AFIX 0 C15 1 0.268195 0.264048 0.485961 10.50000 0.04727 0.05998 = 0.04275 -0.00597 0.03030 -0.00565 AFIX 23 H15A 2 0.251478 0.172590 0.505816 10.50000 -1.20000 H15B 2 0.252857 0.347202 0.516471 10.50000 -1.20000 AFIX 0 C16 1 0.373946 0.265402 0.548252 10.50000 0.04351 0.04434 = 0.03707 -0.00376 0.02590 -0.00507 AFIX 13 H16 2 0.398211 0.163743 0.570458 10.50000 -1.20000 AFIX 66 C22 1 0.441906 0.513129 0.657220 10.50000 0.05299 0.04092 = 0.04630 -0.00503 0.02944 -0.00825 AFIX 43 H22 2 0.411892 0.556036 0.575253 10.50000 -1.20000 AFIX 65 C21 1 0.493818 0.600740 0.769261 10.50000 0.05699 0.04766 = 0.06169 -0.01320 0.03706 -0.01253 AFIX 43 H21 2 0.498537 0.702266 0.762256 10.50000 -1.20000 AFIX 65 C20 1 0.538677 0.536610 0.891770 10.50000 0.05466 0.05641 = 0.04907 -0.01743 0.03086 -0.01012 AFIX 43 H20 2 0.573410 0.595228 0.966732 10.50000 -1.20000 AFIX 65 C19 1 0.531624 0.384867 0.902240 10.50000 0.06232 0.06503 = 0.04045 -0.00604 0.02825 -0.00799 AFIX 43 H19 2 0.561638 0.341961 0.984208 10.50000 -1.20000 AFIX 65 C18 1 0.479712 0.297254 0.790201 10.50000 0.05621 0.04638 = 0.04780 0.00245 0.03221 -0.00134 AFIX 43 H18 2 0.474993 0.195728 0.797207 10.50000 -1.20000 AFIX 65 C17 1 0.434853 0.361383 0.667691 10.50000 0.03511 0.04348 = 0.03784 -0.00128 0.02171 0.00207 AFIX 0 HKLF 4 REM a_a.res in C2/m REM wR2 = 0.1344, GooF = S = 1.086, Restrained GooF = 1.086 for all data REM R1 = 0.0533 for 1263 Fo > 4sig(Fo) and 0.0862 for all 1833 data REM 190 parameters refined using 0 restraints END WGHT 0.0412 0.8304 REM Highest difference peak 0.117, deepest hole -0.123, 1-sigma level 0.027 Q1 1 0.1716 0.5000 0.1488 10.50000 0.05 0.12 Q2 1 0.6631 0.5000 1.0899 10.50000 0.05 0.11 Q3 1 0.2347 0.4359 0.2168 11.00000 0.05 0.10 Q4 1 0.2924 0.0000 0.3294 10.50000 0.05 0.10 Q5 1 0.4584 0.5000 0.5625 10.50000 0.05 0.10 ; _shelx_res_checksum 11100 _olex2_submission_special_instructions 'No special instructions were received' _site XU loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.10449(16) 0.4445(2) 0.2846(2) 0.0616(7) Uani 0.5 1 d . . P A -1 O2 O 0.37459(13) 0.3199(2) 0.44511(18) 0.0425(5) Uani 0.5 1 d . . P A -1 N1 N 0.22092(16) 0.2761(3) 0.3468(2) 0.0407(6) Uani 0.5 1 d . . P A -1 C1 C 0.1590(2) 0.3891(4) 0.2708(3) 0.0454(8) Uani 0.5 1 d . . P A -1 C6 C 0.28428(13) 0.3769(3) 0.1379(2) 0.0511(8) Uani 0.5 1 d G . P A -1 H6 H 0.337761 0.328476 0.160898 0.061 Uiso 0.5 1 calc R U P A -1 C5 C 0.23466(16) 0.4713(3) 0.03029(19) 0.0633(14) Uani 0.5 1 d G . P A -1 H5 H 0.254948 0.486076 -0.018753 0.076 Uiso 0.5 1 calc R U P A -1 C4 C 0.15472(15) 0.5437(3) -0.00404(18) 0.0613(12) Uani 0.5 1 d G . P A -1 H4 H 0.121526 0.606918 -0.076060 0.074 Uiso 0.5 1 calc R U P A -1 C3 C 0.12440(13) 0.5217(3) 0.0693(2) 0.0583(9) Uani 0.5 1 d G . P A -1 H3 H 0.070916 0.570160 0.046283 0.070 Uiso 0.5 1 calc R U P A -1 C2 C 0.17402(14) 0.4273(3) 0.1769(2) 0.0442(7) Uani 0.5 1 d G . P A -1 C7 C 0.25395(13) 0.3549(2) 0.21123(16) 0.0422(7) Uani 0.5 1 d G . P A -1 C8 C 0.2914(2) 0.2593(4) 0.3277(3) 0.0398(7) Uani 0.5 1 d . . P A -1 C11 C 0.2579(2) -0.1548(3) 0.2576(3) 0.0691(12) Uani 0.5 1 d G . P A -1 H11 H 0.212859 -0.227657 0.230143 0.083 Uiso 0.5 1 calc R U P A -1 C10 C 0.23992(14) -0.0089(4) 0.2698(2) 0.0515(8) Uani 0.5 1 d G . P A -1 H10 H 0.182915 0.015927 0.250505 0.062 Uiso 0.5 1 calc R U P A -1 C9 C 0.30719(18) 0.1000(3) 0.3109(2) 0.0424(8) Uani 0.5 1 d G . P A -1 C14 C 0.39239(15) 0.0630(3) 0.3398(2) 0.0577(14) Uani 0.5 1 d G . P A -1 H14 H 0.437397 0.135868 0.367286 0.069 Uiso 0.5 1 calc R U P A -1 C13 C 0.41033(15) -0.0829(4) 0.3276(2) 0.0692(16) Uani 0.5 1 d G . P A -1 H13 H 0.467342 -0.107714 0.346924 0.083 Uiso 0.5 1 calc R U P A -1 C12 C 0.3431(2) -0.1918(3) 0.2865(3) 0.0753(13) Uani 0.5 1 d G . P A -1 H12 H 0.355075 -0.289478 0.278353 0.090 Uiso 0.5 1 calc R U P A -1 C15 C 0.2682(2) 0.2640(4) 0.4860(3) 0.0486(8) Uani 0.5 1 d . . P A -1 H15A H 0.251478 0.172590 0.505816 0.058 Uiso 0.5 1 calc R U P A -1 H15B H 0.252857 0.347202 0.516471 0.058 Uiso 0.5 1 calc R U P A -1 C16 C 0.3739(2) 0.2654(4) 0.5483(3) 0.0412(7) Uani 0.5 1 d . . P A -1 H16 H 0.398211 0.163743 0.570458 0.049 Uiso 0.5 1 calc R U P A -1 C22 C 0.44191(14) 0.5131(2) 0.65722(15) 0.0479(7) Uani 0.5 1 d G . P A -1 H22 H 0.411892 0.556036 0.575253 0.057 Uiso 0.5 1 calc R U P A -1 C21 C 0.49382(17) 0.60074(18) 0.7693(2) 0.0555(9) Uani 0.5 1 d G . P A -1 H21 H 0.498537 0.702266 0.762256 0.067 Uiso 0.5 1 calc R U P A -1 C20 C 0.53868(14) 0.5366(2) 0.89177(17) 0.0545(18) Uani 0.5 1 d G . P A -1 H20 H 0.573410 0.595228 0.966732 0.065 Uiso 0.5 1 calc R U P A -1 C19 C 0.53162(14) 0.3849(2) 0.90224(14) 0.0587(13) Uani 0.5 1 d G . P A -1 H19 H 0.561638 0.341961 0.984208 0.070 Uiso 0.5 1 calc R U P A -1 C18 C 0.47971(15) 0.29725(18) 0.79020(19) 0.0504(8) Uani 0.5 1 d G . P A -1 H18 H 0.474993 0.195728 0.797207 0.060 Uiso 0.5 1 calc R U P A -1 C17 C 0.43485(12) 0.3614(2) 0.66769(15) 0.0396(7) Uani 0.5 1 d G . P A -1 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 0.0621(14) 0.0527(17) 0.0836(17) -0.0025(11) 0.0523(13) 0.0090(11) O2 0.0384(10) 0.0521(14) 0.0350(11) -0.0068(9) 0.0221(9) -0.0082(10) N1 0.0380(13) 0.0421(16) 0.0435(14) -0.0037(11) 0.0262(11) -0.0002(12) C1 0.0408(16) 0.0383(19) 0.0524(19) -0.0080(14) 0.0270(15) -0.0024(14) C6 0.0510(18) 0.057(2) 0.0439(18) -0.0015(16) 0.0291(15) 0.0019(17) C5 0.0680(19) 0.073(4) 0.0452(16) 0.0041(19) 0.0338(14) -0.008(2) C4 0.071(2) 0.051(3) 0.0432(17) 0.0066(13) 0.0267(16) 0.0053(17) C3 0.0489(15) 0.056(3) 0.0556(17) 0.008(2) 0.0258(13) 0.012(2) C2 0.0396(15) 0.0399(17) 0.0417(17) -0.0068(14) 0.0199(13) -0.0029(14) C7 0.0425(16) 0.0414(19) 0.0378(16) -0.0058(13) 0.0228(13) -0.0052(14) C8 0.0358(15) 0.045(2) 0.0357(15) -0.0069(13) 0.0209(13) -0.0038(14) C11 0.091(3) 0.053(3) 0.070(3) -0.016(2) 0.054(3) -0.012(3) C10 0.0593(16) 0.0485(19) 0.0486(15) -0.017(4) 0.0347(13) -0.016(5) C9 0.0424(18) 0.048(2) 0.0328(17) -0.0029(14) 0.0215(14) 0.0041(16) C14 0.0433(19) 0.075(4) 0.046(2) -0.0118(18) 0.0238(18) 0.0048(18) C13 0.068(3) 0.069(3) 0.064(3) -0.010(2) 0.038(2) 0.011(3) C12 0.106(3) 0.052(3) 0.065(3) -0.003(2) 0.052(3) 0.023(3) C15 0.047(2) 0.060(2) 0.0427(17) -0.0060(15) 0.0303(14) -0.0056(17) C16 0.0435(16) 0.0443(19) 0.0371(15) -0.0038(13) 0.0259(14) -0.0051(15) C22 0.0530(14) 0.041(2) 0.0463(13) -0.005(3) 0.0294(12) -0.008(3) C21 0.057(2) 0.048(2) 0.062(2) -0.0132(18) 0.0371(19) -0.0125(18) C20 0.0547(18) 0.056(6) 0.0491(17) -0.0174(16) 0.0309(15) -0.0101(17) C19 0.062(2) 0.065(4) 0.0404(19) -0.0060(19) 0.0282(18) -0.008(2) C18 0.056(2) 0.046(2) 0.0478(19) 0.0024(16) 0.0322(17) -0.0013(17) C17 0.0351(15) 0.043(2) 0.0378(17) -0.0013(14) 0.0217(14) 0.0021(15) 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 C8 O2 C16 104.5(2) . . ? C1 N1 C8 111.3(2) . . ? C1 N1 C15 122.4(3) . . ? C15 N1 C8 108.2(2) . . ? O1 C1 N1 124.8(3) . . ? O1 C1 C2 128.9(3) . . ? N1 C1 C2 106.3(2) . . ? C5 C6 H6 120.0 . . ? C5 C6 C7 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C4 H4 120.0 . . ? C5 C4 C3 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C3 H3 120.0 . . ? C4 C3 C2 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C2 C1 130.73(18) . . ? C7 C2 C1 109.25(18) . . ? C7 C2 C3 120.0 . . ? C6 C7 C8 131.51(17) . . ? C2 C7 C6 120.0 . . ? C2 C7 C8 108.47(17) . . ? O2 C8 N1 103.3(2) . . ? O2 C8 C7 112.0(2) . . ? O2 C8 C9 110.5(2) . . ? N1 C8 C7 103.1(2) . . ? N1 C8 C9 113.1(3) . . ? C7 C8 C9 114.1(2) . . ? C10 C11 H11 120.0 . . ? C10 C11 C12 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C10 H10 120.0 . . ? C9 C10 C11 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C9 C8 121.8(2) . . ? C14 C9 C8 118.2(2) . . ? C14 C9 C10 120.0 . . ? C9 C14 H14 120.0 . . ? C9 C14 C13 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? N1 C15 H15A 111.2 . . ? N1 C15 H15B 111.2 . . ? N1 C15 C16 102.9(2) . . ? H15A C15 H15B 109.1 . . ? C16 C15 H15A 111.2 . . ? C16 C15 H15B 111.2 . . ? O2 C16 C15 104.3(2) . . ? O2 C16 H16 109.2 . . ? O2 C16 C17 110.1(2) . . ? C15 C16 H16 109.2 . . ? C17 C16 C15 114.6(2) . . ? C17 C16 H16 109.2 . . ? C21 C22 H22 120.0 . . ? C21 C22 C17 120.0 . . ? C17 C22 H22 120.0 . . ? C22 C21 H21 120.0 . . ? C22 C21 C20 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C20 H20 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C19 H19 120.0 . . ? C20 C19 C18 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18 120.0 . . ? C22 C17 C16 121.30(19) . . ? C18 C17 C16 118.57(19) . . ? C18 C17 C22 120.0 . . ? 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 C1 1.222(4) . ? O2 C8 1.429(3) . ? O2 C16 1.444(3) . ? N1 C1 1.377(4) . ? N1 C8 1.463(4) . ? N1 C15 1.451(4) . ? C1 C2 1.459(4) . ? C6 H6 0.9300 . ? C6 C5 1.3900 . ? C6 C7 1.3900 . ? C5 H5 0.9300 . ? C5 C4 1.3900 . ? C4 H4 0.9300 . ? C4 C3 1.3900 . ? C3 H3 0.9300 . ? C3 C2 1.3900 . ? C2 C7 1.3900 . ? C7 C8 1.494(3) . ? C8 C9 1.508(4) . ? C11 H11 0.9300 . ? C11 C10 1.3900 . ? C11 C12 1.3900 . ? C10 H10 0.9300 . ? C10 C9 1.3900 . ? C9 C14 1.3900 . ? C14 H14 0.9300 . ? C14 C13 1.3900 . ? C13 H13 0.9300 . ? C13 C12 1.3900 . ? C12 H12 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.553(4) . ? C16 H16 0.9800 . ? C16 C17 1.501(3) . ? C22 H22 0.9300 . ? C22 C21 1.3900 . ? C22 C17 1.3900 . ? C21 H21 0.9300 . ? C21 C20 1.3900 . ? C20 H20 0.9300 . ? C20 C19 1.3900 . ? C19 H19 0.9300 . ? C19 C18 1.3900 . ? C18 H18 0.9300 . ? C18 C17 1.3900 . ? 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 C3 -8.9(5) . . . . ? O1 C1 C2 C7 169.2(3) . . . . ? O2 C8 C9 C10 137.5(2) . . . . ? O2 C8 C9 C14 -41.5(3) . . . . ? O2 C16 C17 C22 34.5(3) . . . . ? O2 C16 C17 C18 -149.80(18) . . . . ? N1 C1 C2 C3 172.28(17) . . . . ? N1 C1 C2 C7 -9.6(3) . . . . ? N1 C8 C9 C10 22.2(3) . . . . ? N1 C8 C9 C14 -156.76(18) . . . . ? N1 C15 C16 O2 15.9(3) . . . . ? N1 C15 C16 C17 136.3(3) . . . . ? C1 N1 C8 O2 105.8(3) . . . . ? C1 N1 C8 C7 -10.9(3) . . . . ? C1 N1 C8 C9 -134.7(2) . . . . ? C1 N1 C15 C16 -122.3(3) . . . . ? C1 C2 C7 C6 -178.4(2) . . . . ? C1 C2 C7 C8 2.8(2) . . . . ? C6 C5 C4 C3 0.0 . . . . ? C6 C7 C8 O2 75.5(3) . . . . ? C6 C7 C8 N1 -174.08(18) . . . . ? C6 C7 C8 C9 -51.0(3) . . . . ? C5 C6 C7 C2 0.0 . . . . ? C5 C6 C7 C8 178.5(2) . . . . ? C5 C4 C3 C2 0.0 . . . . ? C4 C3 C2 C1 178.0(3) . . . . ? C4 C3 C2 C7 0.0 . . . . ? C3 C2 C7 C6 0.0 . . . . ? C3 C2 C7 C8 -178.8(2) . . . . ? C2 C7 C8 O2 -105.9(2) . . . . ? C2 C7 C8 N1 4.6(2) . . . . ? C2 C7 C8 C9 127.6(2) . . . . ? C7 C6 C5 C4 0.0 . . . . ? C7 C8 C9 C10 -95.2(2) . . . . ? C7 C8 C9 C14 85.8(2) . . . . ? C8 O2 C16 C15 -35.8(3) . . . . ? C8 O2 C16 C17 -159.1(2) . . . . ? C8 N1 C1 O1 -166.1(3) . . . . ? C8 N1 C1 C2 12.8(3) . . . . ? C8 N1 C15 C16 9.2(3) . . . . ? C8 C9 C14 C13 179.0(2) . . . . ? C11 C10 C9 C8 -179.0(2) . . . . ? C11 C10 C9 C14 0.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C10 C9 C14 C13 0.0 . . . . ? C9 C14 C13 C12 0.0 . . . . ? C14 C13 C12 C11 0.0 . . . . ? C12 C11 C10 C9 0.0 . . . . ? C15 N1 C1 O1 -35.8(5) . . . . ? C15 N1 C1 C2 143.0(3) . . . . ? C15 N1 C8 O2 -31.4(3) . . . . ? C15 N1 C8 C7 -148.2(2) . . . . ? C15 N1 C8 C9 88.1(3) . . . . ? C15 C16 C17 C22 -82.7(3) . . . . ? C15 C16 C17 C18 93.1(3) . . . . ? C16 O2 C8 N1 41.6(3) . . . . ? C16 O2 C8 C7 151.8(2) . . . . ? C16 O2 C8 C9 -79.7(3) . . . . ? C22 C21 C20 C19 0.0 . . . . ? C21 C22 C17 C16 175.7(2) . . . . ? C21 C22 C17 C18 0.0 . . . . ? C21 C20 C19 C18 0.0 . . . . ? C20 C19 C18 C17 0.0 . . . . ? C19 C18 C17 C16 -175.8(2) . . . . ? C19 C18 C17 C22 0.0 . . . . ? C17 C22 C21 C20 0.0 . . . . ?