#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014371.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014371 loop_ _publ_author_name ' Xiang Zhou' ' Xiao-Bing Wang' ' Ling-Yi Kong' _publ_section_title ;Hydrogen bonding and \p--\p stacking in 7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one monohydrate ; _journal_coeditor_code LN1189 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o58 _journal_page_last o61 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C23 H26 N2 O4, H2 O' _chemical_formula_moiety 'C23 H26 N2 O4, H2 O' _chemical_formula_sum 'C23 H28 N2 O5' _chemical_formula_weight 412.47 _chemical_name_systematic ; 7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2H-chromen-2-one monohydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 99.406(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.776(7) _cell_length_b 7.483(5) _cell_length_c 26.381(18) _cell_measurement_reflns_used 2841 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.083 _cell_measurement_theta_min 2.185 _cell_volume 2099(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL and WinGX (Version 1.7; Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 10516 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.18 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.166 _refine_diff_density_min -0.224 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3684 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0456 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.055P)^2^+0.28P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.1235 _reflns_number_gt 2296 _reflns_number_total 3684 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln1189.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2014371 loop_ _symmetry_equiv_pos_as_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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.53174(16) 0.7986(2) 0.12525(6) 0.0505(5) Uani d . 1 . . N N2 0.31370(15) 0.8865(2) 0.17170(6) 0.0456(4) Uani d . 1 . . N O1 1.17834(14) 0.76897(18) -0.00482(5) 0.0523(4) Uani d . 1 . . O O2 1.36372(17) 0.7424(2) -0.02888(6) 0.0759(5) Uani d . 1 . . O O3 0.80421(14) 0.8368(2) 0.05953(6) 0.0619(4) Uani d . 1 . . O O4 -0.15187(14) 0.9134(2) 0.23986(6) 0.0660(5) Uani d . 1 . . O O5 0.47771(17) 0.4188(2) 0.09991(7) 0.0875(6) Uani d D 1 . . O H5A 0.4900 0.5342 0.1045 0.105 Uiso d RD 1 . . H H5B 0.5127 0.4031 0.0728 0.105 Uiso d RD 1 . . H C1 1.2518(2) 0.7162(3) -0.04013(8) 0.0562(6) Uani d . 1 . . C C2 1.1882(2) 0.6361(3) -0.08669(8) 0.0579(6) Uani d . 1 . . C H2 1.2357 0.6023 -0.1116 0.069 Uiso calc R 1 . . H C3 1.0639(2) 0.6078(3) -0.09596(7) 0.0526(6) Uani d . 1 . . C C4 0.9889(2) 0.6635(2) -0.05837(7) 0.0454(5) Uani d . 1 . . C C5 0.8588(2) 0.6460(3) -0.06280(8) 0.0546(6) Uani d . 1 . . C H5 0.8145 0.5948 -0.0925 0.066 Uiso calc R 1 . . H C6 0.7934(2) 0.7013(3) -0.02513(8) 0.0541(6) Uani d . 1 . . C H6 0.7066 0.6872 -0.0293 0.065 Uiso calc R 1 . . H C7 0.8583(2) 0.7787(3) 0.01941(8) 0.0475(5) Uani d . 1 . . C C8 0.9869(2) 0.7992(3) 0.02532(7) 0.0470(5) Uani d . 1 . . C H8 1.0307 0.8503 0.0551 0.056 Uiso calc R 1 . . H C9 1.0498(2) 0.7438(2) -0.01305(7) 0.0443(5) Uani d . 1 . . C C10 1.0030(3) 0.5162(3) -0.14454(8) 0.0743(8) Uani d . 1 . . C H10A 0.9370 0.5904 -0.1621 0.111 Uiso calc R 1 . . H H10B 0.9685 0.4038 -0.1361 0.111 Uiso calc R 1 . . H H10C 1.0648 0.4959 -0.1663 0.111 Uiso calc R 1 . . H C11 0.6738(2) 0.8042(3) 0.05988(8) 0.0569(6) Uani d . 1 . . C H11A 0.6524 0.6810 0.0509 0.068 Uiso calc R 1 . . H H11B 0.6219 0.8823 0.0359 0.068 Uiso calc R 1 . . H C12 0.6566(2) 0.8438(3) 0.11425(8) 0.0611(6) Uani d . 1 . . C H12A 0.7190 0.7775 0.1375 0.073 Uiso calc R 1 . . H H12B 0.6718 0.9700 0.1210 0.073 Uiso calc R 1 . . H C13 0.5342(2) 0.8006(3) 0.18101(8) 0.0580(6) Uani d . 1 . . C H13A 0.5620 0.9172 0.1944 0.070 Uiso calc R 1 . . H H13B 0.5945 0.7128 0.1969 0.070 Uiso calc R 1 . . H C14 0.4084(2) 0.7606(3) 0.19534(8) 0.0572(6) Uani d . 1 . . C H14A 0.3832 0.6403 0.1844 0.069 Uiso calc R 1 . . H H14B 0.4145 0.7662 0.2324 0.069 Uiso calc R 1 . . H C15 0.3096(2) 0.8845(3) 0.11589(7) 0.0570(6) Uani d . 1 . . C H15A 0.2487 0.9719 0.1001 0.068 Uiso calc R 1 . . H H15B 0.2823 0.7677 0.1026 0.068 Uiso calc R 1 . . H C16 0.4362(2) 0.9263(3) 0.10182(8) 0.0580(6) Uani d . 1 . . C H16A 0.4304 0.9226 0.0648 0.070 Uiso calc R 1 . . H H16B 0.4612 1.0461 0.1133 0.070 Uiso calc R 1 . . H C17 0.19665(19) 0.8838(2) 0.18936(7) 0.0421(5) Uani d . 1 . . C C18 0.1749(2) 0.7849(3) 0.23161(7) 0.0508(5) Uani d . 1 . . C H18 0.2387 0.7119 0.2483 0.061 Uiso calc R 1 . . H C19 0.0613(2) 0.7915(3) 0.24977(7) 0.0517(6) Uani d . 1 . . C H19 0.0506 0.7250 0.2785 0.062 Uiso calc R 1 . . H C20 -0.0357(2) 0.8961(3) 0.22545(7) 0.0485(5) Uani d . 1 . . C C21 -0.0158(2) 0.9946(3) 0.18305(8) 0.0524(6) Uani d . 1 . . C H21 -0.0804 1.0653 0.1660 0.063 Uiso calc R 1 . . H C22 0.0970(2) 0.9897(3) 0.16589(7) 0.0499(5) Uani d . 1 . . C H22 0.1078 1.0590 0.1377 0.060 Uiso calc R 1 . . H C23 -0.1775(2) 0.8104(4) 0.28198(9) 0.0760(8) Uani d . 1 . . C H23A -0.2593 0.8406 0.2893 0.114 Uiso calc R 1 . . H H23B -0.1153 0.8350 0.3116 0.114 Uiso calc R 1 . . H H23C -0.1753 0.6857 0.2736 0.114 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0525(11) 0.0517(11) 0.0468(10) -0.0007(9) 0.0067(8) 0.0028(8) N2 0.0516(11) 0.0458(10) 0.0379(9) 0.0043(8) 0.0028(8) 0.0063(7) O1 0.0602(10) 0.0522(9) 0.0457(8) -0.0058(7) 0.0123(7) -0.0056(7) O2 0.0662(12) 0.0896(14) 0.0756(11) -0.0065(10) 0.0226(9) -0.0157(9) O3 0.0566(10) 0.0688(11) 0.0625(9) -0.0072(8) 0.0163(8) -0.0108(8) O4 0.0641(11) 0.0767(12) 0.0598(9) 0.0069(9) 0.0180(8) 0.0089(8) O5 0.0984(14) 0.0706(12) 0.0981(13) -0.0173(10) 0.0296(11) -0.0117(10) C1 0.0703(17) 0.0490(14) 0.0525(13) -0.0014(12) 0.0197(13) 0.0026(11) C2 0.0834(18) 0.0475(14) 0.0467(13) -0.0015(12) 0.0223(12) -0.0002(10) C3 0.0856(18) 0.0316(12) 0.0414(11) -0.0044(11) 0.0125(12) 0.0024(9) C4 0.0672(15) 0.0296(11) 0.0384(11) -0.0055(10) 0.0056(10) 0.0040(9) C5 0.0731(17) 0.0442(13) 0.0429(12) -0.0119(11) -0.0019(11) 0.0014(10) C6 0.0559(14) 0.0512(14) 0.0535(13) -0.0068(11) 0.0035(11) 0.0080(11) C7 0.0588(15) 0.0368(12) 0.0471(12) -0.0017(10) 0.0091(11) 0.0041(9) C8 0.0569(14) 0.0434(13) 0.0399(11) -0.0034(10) 0.0054(10) -0.0015(9) C9 0.0547(14) 0.0322(11) 0.0451(11) -0.0045(9) 0.0058(10) 0.0061(9) C10 0.110(2) 0.0630(16) 0.0500(13) -0.0117(15) 0.0134(14) -0.0141(12) C11 0.0513(14) 0.0566(14) 0.0628(14) -0.0044(11) 0.0090(11) 0.0024(11) C12 0.0591(15) 0.0631(16) 0.0614(14) -0.0040(12) 0.0111(12) -0.0027(12) C13 0.0578(15) 0.0645(15) 0.0488(12) 0.0065(12) 0.0001(11) 0.0042(11) C14 0.0591(14) 0.0654(15) 0.0452(11) 0.0092(12) 0.0033(11) 0.0141(11) C15 0.0580(14) 0.0681(15) 0.0434(12) 0.0072(12) 0.0038(10) 0.0107(11) C16 0.0637(15) 0.0589(15) 0.0519(13) 0.0050(12) 0.0114(11) 0.0132(11) C17 0.0514(13) 0.0349(11) 0.0380(10) -0.0017(10) 0.0013(10) -0.0010(9) C18 0.0602(14) 0.0445(13) 0.0451(12) 0.0035(11) 0.0007(11) 0.0076(10) C19 0.0648(15) 0.0491(13) 0.0410(11) -0.0030(11) 0.0082(11) 0.0064(10) C20 0.0547(14) 0.0456(13) 0.0442(11) -0.0021(11) 0.0054(11) -0.0041(10) C21 0.0592(15) 0.0455(13) 0.0507(12) 0.0092(11) 0.0035(11) 0.0043(10) C22 0.0630(15) 0.0429(12) 0.0428(11) 0.0038(11) 0.0055(11) 0.0075(10) C23 0.0715(17) 0.096(2) 0.0632(15) -0.0050(15) 0.0203(13) 0.0125(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C16 . 1.465(3) yes N1 C12 . 1.461(3) yes N1 C13 . 1.467(3) yes N2 C17 . 1.414(3) yes N2 C14 . 1.452(2) yes N2 C15 . 1.466(3) yes O1 C1 . 1.375(3) ? O1 C9 . 1.380(3) ? O2 C1 . 1.210(3) ? O3 C7 . 1.360(2) ? O3 C11 . 1.428(3) ? O4 C20 . 1.373(2) ? O4 C23 . 1.416(3) ? O5 H5A . 0.8786 ? O5 H5B . 0.8689 ? C1 C2 . 1.436(3) ? C2 C3 . 1.338(3) ? C2 H2 . 0.9300 ? C3 C4 . 1.440(3) ? C3 C10 . 1.506(3) ? C4 C5 . 1.394(3) ? C4 C9 . 1.401(3) ? C5 C6 . 1.373(3) ? C5 H5 . 0.9300 ? C6 C7 . 1.391(3) ? C6 H6 . 0.9300 ? C7 C8 . 1.378(3) ? C8 C9 . 1.371(3) ? C8 H8 . 0.9300 ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? C11 C12 . 1.505(3) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? C13 C14 . 1.496(3) yes C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 H14A . 0.9700 ? C14 H14B . 0.9700 ? C15 C16 . 1.505(3) yes C15 H15A . 0.9700 ? C15 H15B . 0.9700 ? C16 H16A . 0.9700 ? C16 H16B . 0.9700 ? C17 C18 . 1.389(3) ? C17 C22 . 1.395(3) ? C18 C19 . 1.386(3) ? C18 H18 . 0.9300 ? C19 C20 . 1.377(3) ? C19 H19 . 0.9300 ? C20 C21 . 1.385(3) ? C21 C22 . 1.365(3) ? C21 H21 . 0.9300 ? C22 H22 . 0.9300 ? C23 H23A . 0.9600 ? C23 H23B . 0.9600 ? C23 H23C . 0.9600 ? 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_publ_flag C16 N1 C12 111.81(17) yes C16 N1 C13 108.22(17) yes C12 N1 C13 109.31(16) yes C17 N2 C14 116.81(15) yes C17 N2 C15 116.63(16) yes C14 N2 C15 109.19(16) yes C1 O1 C9 121.91(17) ? C7 O3 C11 119.84(17) ? C20 O4 C23 118.00(17) ? H5A O5 H5B 99.9 ? O2 C1 O1 116.6(2) ? O2 C1 C2 126.5(2) ? O1 C1 C2 116.9(2) ? C3 C2 C1 123.1(2) ? C3 C2 H2 118.5 ? C1 C2 H2 118.5 ? C2 C3 C4 119.1(2) ? C2 C3 C10 120.8(2) ? C4 C3 C10 120.1(2) ? C5 C4 C9 115.84(19) ? C5 C4 C3 125.8(2) ? C9 C4 C3 118.3(2) ? C6 C5 C4 122.6(2) ? C6 C5 H5 118.7 ? C4 C5 H5 118.7 ? C5 C6 C7 119.4(2) ? C5 C6 H6 120.3 ? C7 C6 H6 120.3 ? O3 C7 C8 115.28(18) ? O3 C7 C6 124.8(2) ? C8 C7 C6 119.9(2) ? C9 C8 C7 119.50(19) ? C9 C8 H8 120.2 ? C7 C8 H8 120.2 ? C8 C9 O1 116.58(18) ? C8 C9 C4 122.7(2) ? O1 C9 C4 120.70(19) ? C3 C10 H10A 109.5 ? C3 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C3 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? O3 C11 C12 104.33(17) ? O3 C11 H11A 110.9 ? C12 C11 H11A 110.9 ? O3 C11 H11B 110.9 ? C12 C11 H11B 110.9 ? H11A C11 H11B 108.9 ? N1 C12 C11 113.87(18) ? N1 C12 H12A 108.8 ? C11 C12 H12A 108.8 ? N1 C12 H12B 108.8 ? C11 C12 H12B 108.8 ? H12A C12 H12B 107.7 ? N1 C13 C14 112.53(17) yes N1 C13 H13A 109.1 ? C14 C13 H13A 109.1 ? N1 C13 H13B 109.1 ? C14 C13 H13B 109.1 ? H13A C13 H13B 107.8 ? N2 C14 C13 111.34(17) yes N2 C14 H14A 109.4 ? C13 C14 H14A 109.4 ? N2 C14 H14B 109.4 ? C13 C14 H14B 109.4 ? H14A C14 H14B 108.0 ? N2 C15 C16 111.45(17) yes N2 C15 H15A 109.3 ? C16 C15 H15A 109.3 ? N2 C15 H15B 109.3 ? C16 C15 H15B 109.3 ? H15A C15 H15B 108.0 ? N1 C16 C15 111.33(17) yes N1 C16 H16A 109.4 ? C15 C16 H16A 109.4 ? N1 C16 H16B 109.4 ? C15 C16 H16B 109.4 ? H16A C16 H16B 108.0 ? C18 C17 C22 116.11(19) ? C18 C17 N2 123.24(18) ? C22 C17 N2 120.59(17) ? C19 C18 C17 122.16(19) ? C19 C18 H18 118.9 ? C17 C18 H18 118.9 ? C20 C19 C18 120.34(19) ? C20 C19 H19 119.8 ? C18 C19 H19 119.8 ? O4 C20 C19 125.57(19) ? O4 C20 C21 116.21(19) ? C19 C20 C21 118.2(2) ? C22 C21 C20 121.1(2) ? C22 C21 H21 119.4 ? C20 C21 H21 119.4 ? C21 C22 C17 122.04(19) ? C21 C22 H22 119.0 ? C17 C22 H22 119.0 ? O4 C23 H23A 109.5 ? O4 C23 H23B 109.5 ? H23A C23 H23B 109.5 ? O4 C23 H23C 109.5 ? H23A C23 H23C 109.5 ? H23B C23 H23C 109.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O5 H5A N1 . 0.88 2.08 2.955(3) 172 O5 H5B O2 3_765 0.87 2.19 2.989(3) 152 C6 H6 O5 3_665 0.93 2.61 3.369(3) 139 C23 H23B O5 2 0.96 2.63 3.579(4) 170 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_publ_flag C9 O1 C1 O2 -179.06(19) ? C9 O1 C1 C2 1.1(3) ? O2 C1 C2 C3 178.4(2) ? O1 C1 C2 C3 -1.7(3) ? C1 C2 C3 C4 1.5(3) ? C1 C2 C3 C10 -177.4(2) ? C2 C3 C4 C5 178.9(2) ? C10 C3 C4 C5 -2.1(3) ? C2 C3 C4 C9 -0.7(3) ? C10 C3 C4 C9 178.23(19) ? C9 C4 C5 C6 -0.8(3) ? C3 C4 C5 C6 179.57(19) ? C4 C5 C6 C7 0.2(3) ? C11 O3 C7 C8 -173.17(18) ? C11 O3 C7 C6 6.2(3) ? C5 C6 C7 O3 -179.25(19) ? C5 C6 C7 C8 0.0(3) ? O3 C7 C8 C9 179.71(18) ? C6 C7 C8 C9 0.3(3) ? C7 C8 C9 O1 179.68(17) ? C7 C8 C9 C4 -1.0(3) ? C1 O1 C9 C8 178.94(18) ? C1 O1 C9 C4 -0.4(3) ? C5 C4 C9 C8 1.2(3) ? C3 C4 C9 C8 -179.13(18) ? C5 C4 C9 O1 -179.52(17) ? C3 C4 C9 O1 0.2(3) ? C7 O3 C11 C12 166.23(18) ? C16 N1 C12 C11 -73.8(2) ? C13 N1 C12 C11 166.38(19) ? O3 C11 C12 N1 -173.07(17) ? C16 N1 C13 C14 56.4(2) ? C12 N1 C13 C14 178.35(18) ? C17 N2 C14 C13 -168.91(17) ? C15 N2 C14 C13 56.0(2) ? N1 C13 C14 N2 -57.7(2) yes C17 N2 C15 C16 168.08(17) ? C14 N2 C15 C16 -56.8(2) ? C12 N1 C16 C15 -176.75(17) ? C13 N1 C16 C15 -56.3(2) ? N2 C15 C16 N1 58.4(2) yes C14 N2 C17 C18 8.4(3) ? C15 N2 C17 C18 140.1(2) ? C14 N2 C17 C22 -174.68(18) ? C15 N2 C17 C22 -43.0(3) ? C22 C17 C18 C19 -0.5(3) ? N2 C17 C18 C19 176.64(18) ? C17 C18 C19 C20 1.1(3) ? C23 O4 C20 C19 -2.7(3) yes C23 O4 C20 C21 177.91(19) yes C18 C19 C20 O4 -179.94(19) ? C18 C19 C20 C21 -0.6(3) ? O4 C20 C21 C22 178.93(18) ? C19 C20 C21 C22 -0.5(3) ? C20 C21 C22 C17 1.1(3) ? C18 C17 C22 C21 -0.6(3) ? N2 C17 C22 C21 -177.82(18) ? _journal_paper_doi 10.1107/S0108270105040928