#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011472.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_2011472 loop_ _publ_author_name 'Hu, Zhi Zhi' 'Takami, Shizuka' 'Kimura, Masaru' 'Tachi, Yoshimitsu' 'Naruta, Yoshinori' _publ_section_title ; 2,4,5-Triphenyl-4H-imidazol-4-yl hydroperoxide--dichloromethane (2/1) ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e465 _journal_page_last e466 _journal_paper_doi 10.1107/S0108270100011720 _journal_volume 56 _journal_year 2000 _chemical_formula_iupac '2C21 H16 N2 O2, C H2 Cl2' _chemical_formula_moiety 'C43 H34 Cl2 N4 O4' _chemical_formula_sum 'C43 H34 Cl2 N4 O4' _chemical_formula_weight 741.67 _chemical_melting_point 115 _chemical_name_systematic ; 2,4,5-Triphenyl-4H-imidazol-4-yl-hydroperoxide dichloromethane solvate (2:1) ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 94.456(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.5190(10) _cell_length_b 14.2690(10) _cell_length_c 26.068(2) _cell_measurement_reflns_used 14799 _cell_measurement_temperature 123.2 _cell_measurement_theta_max 68.0 _cell_measurement_theta_min 4.1 _cell_volume 7238.4(8) _computing_cell_refinement ; MSC/RAXIS-RAPID Imaging Plate Diffractometer Control Software ; _computing_data_collection ; MSC/RAXIS-RAPID Imaging Plate Diffractometer Control Software (Molecular Structure Corporation, 1996) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .078 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 33961 _diffrn_reflns_theta_max 68.0 _diffrn_reflns_theta_min 4.1 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.021 _exptl_absorpt_correction_T_max .524 _exptl_absorpt_correction_T_min .460 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.361 _exptl_crystal_description prism _exptl_crystal_F_000 3088 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .32 _refine_diff_density_max .65 _refine_diff_density_min -.99 _refine_ls_extinction_coef .0048(6) _refine_ls_extinction_method 'Zachariasen (1967) type 2 Gaussian isotropic' _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 479 _refine_ls_number_reflns 6464 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max .0010 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.06000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^])' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .142 _reflns_number_gt 4887 _reflns_number_total 6464 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qd0033.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^) + (0.06000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^])' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^) + (0.06000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^])'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 7238.5(8) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2011472 _cod_database_fobs_code 2011472 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z 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 Cl1 .40322(4) .17763(5) .01415(3) .0485(2) Uani d . 1.00 . . Cl Cl2 .51833(5) .29661(9) -.00407(4) .0780(3) Uani d . 1.00 . . Cl O1 -.05768(8) .86110(10) .32699(5) .0208(4) Uani d . 1.00 . . O O1' -.10842(8) 1.07360(10) .29438(5) .0204(4) Uani d . 1.00 . . O O2 -.04542(8) .88100(10) .38227(6) .0243(4) Uani d . 1.00 . . O O2' -.18213(8) 1.05350(10) .29260(6) .0232(4) Uani d . 1.00 . . O N1 -.17736(10) .87650(10) .33548(7) .0211(4) Uani d . 1.00 . . N N1' -.10067(10) 1.05960(10) .38635(7) .0203(4) Uani d . 1.00 . . N N2 -.17650(10) .74240(10) .38580(7) .0227(5) Uani d . 1.00 . . N N2' -.16336(10) 1.19590(10) .39420(7) .0217(4) Uani d . 1.00 . . N C1 -.20460(10) .8330(2) .37215(8) .0205(5) Uani d . 1.00 . . C C1' -.13980(10) 1.1072(2) .41426(8) .0210(5) Uani d . 1.00 . . C C2 -.12230(10) .81560(10) .31965(8) .0194(5) Uani d . 1.00 . . C C2' -.08980(10) 1.11980(10) .34156(8) .0192(5) Uani d . 1.00 . . C C3 -.12730(10) .73040(10) .35590(8) .0204(5) Uani d . 1.00 . . C C3' -.13540(10) 1.20450(10) .35116(8) .0191(5) Uani d . 1.00 . . C C4 -.25930(10) .8701(2) .40186(8) .0222(5) Uani d . 1.00 . . C C4' -.15970(10) 1.0783(2) .46517(8) .0235(5) Uani d . 1.00 . . C C5 -.29180(10) .9548(2) .38770(9) .0262(6) Uani d . 1.00 . . C C5' -.1264(2) 1.0034(2) .49082(10) .0402(7) Uani d . 1.00 . . C C6 -.34220(10) .9897(2) .41671(9) .0300(6) Uani d . 1.00 . . C C6' -.1448(2) .9783(2) .53940(10) .0485(9) Uani d . 1.00 . . C C7 -.36050(10) .9423(2) .45990(10) .0335(7) Uani d . 1.00 . . C C7' -.1960(2) 1.0264(2) .56199(10) .0415(7) Uani d . 1.00 . . C C8 -.32830(10) .8582(2) .47438(10) .0364(7) Uani d . 1.00 . . C C8' -.22950(10) 1.1001(2) .53637(10) .0362(7) Uani d . 1.00 . . C C9 -.27800(10) .8221(2) .44524(9) .0295(6) Uani d . 1.00 . . C C9' -.21140(10) 1.1264(2) .48804(9) .0284(6) Uani d . 1.00 . . C C10 -.13230(10) .7922(2) .26245(8) .0191(5) Uani d . 1.00 . . C C10' -.01350(10) 1.1402(2) .34167(8) .0214(5) Uani d . 1.00 . . C C11 -.09970(10) .8456(2) .22715(9) .0264(6) Uani d . 1.00 . . C C12' .02990(10) 1.0750(2) .32130(8) .0250(5) Uani d . 1.00 . . C C12 -.10890(10) .8247(2) .17486(9) .0308(6) Uani d . 1.00 . . C C12' .10020(10) 1.0908(2) .32342(9) .0266(6) Uani d . 1.00 . . C C13 -.15160(10) .7515(2) .15802(9) .0273(6) Uani d . 1.00 . . C C13' .12770(10) 1.1717(2) .34617(9) .0288(6) Uani d . 1.00 . . C C14 -.18500(10) .6991(2) .19318(9) .0270(6) Uani d . 1.00 . . C C14' .08460(10) 1.2362(2) .36662(10) .0293(6) Uani d . 1.00 . . C C15 -.17510(10) .7193(2) .24562(9) .0247(6) Uani d . 1.00 . . C C15' .01420(10) 1.2218(2) .36444(9) .0267(6) Uani d . 1.00 . . C C16 -.08400(10) .6478(2) .35662(8) .0216(5) Uani d . 1.00 . . C C16' -.14540(10) 1.2858(2) .31740(8) .0197(5) Uani d . 1.00 . . C C17 -.03090(10) .6397(2) .32381(9) .0260(6) Uani d . 1.00 . . C C17' -.11150(10) 1.2946(2) .27269(9) .0264(6) Uani d . 1.00 . . C C18 .00840(10) .5586(2) .32408(10) .0306(6) Uani d . 1.00 . . C C18' -.1210(2) 1.3742(2) .24224(9) .0328(6) Uani d . 1.00 . . C C19 -.00450(10) .4860(2) .35720(10) .0328(6) Uani d . 1.00 . . C C19' -.16510(10) 1.4444(2) .25566(9) .0329(6) Uani d . 1.00 . . C C20 -.05620(10) .4941(2) .39064(10) .0317(6) Uani d . 1.00 . . C C20' -.20010(10) 1.4358(2) .29952(9) .0299(6) Uani d . 1.00 . . C C21 -.09600(10) .5742(2) .39048(9) .0277(6) Uani d . 1.00 . . C C21' -.19060(10) 1.3574(2) .33045(8) .0253(6) Uani d . 1.00 . . C C22 .45810(10) .2665(2) .03932(10) .0352(7) Uani d . 1.00 . . C H5 -.2822 .9848 .3558 .0480 Uiso calc . 1.00 . . H H5' -.0843 .9747 .4784 .0480 Uiso calc . 1.00 . . H H6 -.3665 1.0452 .4060 .0480 Uiso calc . 1.00 . . H H6' -.1222 .9279 .5565 .0480 Uiso calc . 1.00 . . H H7 -.3999 .9652 .4803 .0480 Uiso calc . 1.00 . . H H7' -.2101 1.0080 .5970 .0480 Uiso calc . 1.00 . . H H8 -.3433 .8216 .5056 .0480 Uiso calc . 1.00 . . H H8' -.2655 1.1397 .5525 .0480 Uiso calc . 1.00 . . H H9 -.2569 .7626 .4556 .0480 Uiso calc . 1.00 . . H H9' -.2379 1.1768 .4673 .0480 Uiso calc . 1.00 . . H H11 -.0695 .8965 .2363 .0480 Uiso calc . 1.00 . . H H11' .0119 1.0182 .3059 .0480 Uiso calc . 1.00 . . H H12 -.0856 .8595 .1519 .0480 Uiso calc . 1.00 . . H H12' .1298 1.0438 .3091 .0480 Uiso calc . 1.00 . . H H13 -.1647 .7395 .1211 .0480 Uiso calc . 1.00 . . H H13' .1779 1.1825 .3447 .0480 Uiso calc . 1.00 . . H H14 -.2155 .6487 .1819 .0480 Uiso calc . 1.00 . . H H14' .1065 1.2905 .3839 .0480 Uiso calc . 1.00 . . H H15 -.2028 .6834 .2668 .0480 Uiso calc . 1.00 . . H H15' -.0195 1.2696 .3773 .0480 Uiso calc . 1.00 . . H H17 -.0198 .6893 .2987 .0480 Uiso calc . 1.00 . . H H17' -.0787 1.2451 .2626 .0480 Uiso calc . 1.00 . . H H18 .0436 .5526 .2991 .0480 Uiso calc . 1.00 . . H H18' -.0981 1.3766 .2122 .0480 Uiso calc . 1.00 . . H H19 .0245 .4289 .3582 .0480 Uiso calc . 1.00 . . H H19' -.1709 1.4991 .2361 .0480 Uiso calc . 1.00 . . H H20 -.0575 .4477 .4185 .0480 Uiso calc . 1.00 . . H H20' -.2299 1.4826 .3111 .0480 Uiso calc . 1.00 . . H H21 -.1363 .5815 .4154 .0480 Uiso calc . 1.00 . . H H21' -.2153 1.3544 .3618 .0480 Uiso calc . 1.00 . . H H22 .4796 .2454 .0695 .0480 Uiso calc . 1.00 . . H H22' .4337 .3267 .0454 .0480 Uiso calc . 1.00 . . H H2o' -.1840 .9893 .3085 .0480 Uiso calc . 1.00 . . H H2o -.0660 .9448 .3852 .0480 Uiso calc . 1.00 . . 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 Cl1 .0581(5) .0375(4) .0495(4) -.0204(3) .0015(3) -.0035(3) Cl2 .0741(6) .1016(8) .0636(5) -.0521(6) .0391(5) -.0310(5) O1 .0220(8) .0207(8) .0194(7) -.0006(6) .0003(6) -.0027(6) O1' .0214(7) .0187(8) .0213(7) -.0006(6) .0034(6) -.0029(6) O2 .0291(8) .0216(8) .0215(7) .0027(7) -.0038(6) -.0031(6) O2' .0211(8) .0192(8) .0294(8) .0003(6) .0017(6) .0029(6) N1 .0221(9) .0175(9) .0236(9) .0016(7) .0013(7) -.0008(7) N1' .0258(9) .0157(9) .0196(8) -.0012(7) .0039(7) -.0001(7) N2 .0265(9) .0175(9) .0246(9) .0021(8) .0047(7) .0007(7) N2' .0270(10) .0175(9) .0209(8) .0013(8) .0036(7) -.0004(7) C1 .0230(10) .0170(10) .0210(10) .0017(8) .0006(8) .0001(8) C1' .0260(10) .0160(10) .0212(10) .0001(9) .0019(8) -.0025(8) C2 .0188(10) .0152(10) .0240(10) .0000(8) .0017(8) .0020(8) C2' .0260(10) .0133(10) .0186(9) -.0004(8) .0023(8) .0004(7) C3 .0240(10) .0160(10) .0215(9) -.0014(9) .0018(8) .0005(8) C3' .0220(10) .0151(10) .0196(9) -.0029(8) -.0009(8) -.0020(7) C4 .0210(10) .0220(10) .0230(10) .0000(9) .0008(8) -.0027(8) C4' .0300(10) .0220(10) .0188(10) -.0017(10) .0028(9) -.0013(8) C5 .0280(10) .0230(10) .0280(10) .0017(10) .0018(9) .0000(9) C5' .063(2) .0330(10) .0270(10) .0170(10) .0150(10) .0070(10) C6 .0310(10) .0270(10) .0320(10) .0090(10) .0014(10) -.0036(9) C6' .083(2) .036(2) .0290(10) .020(2) .0160(10) .0130(10) C7 .0300(10) .0360(10) .0360(10) .0100(10) .0100(10) -.0070(10) C7' .060(2) .044(2) .0230(10) .0060(10) .0120(10) .0080(10) C8 .0380(10) .044(2) .0290(10) .0110(10) .0110(10) .0030(10) C8' .0390(10) .045(2) .0260(10) .0050(10) .0100(10) .0020(10) C9 .0310(10) .0320(10) .0260(10) .0070(10) .0034(10) .0029(9) C9' .0320(10) .0320(10) .0220(10) .0060(10) .0032(9) .0019(9) C10 .0172(10) .0170(10) .0225(10) .0030(8) -.0005(8) -.0011(8) C10' .0270(10) .0180(10) .0198(9) .0025(9) .0031(8) .0013(8) C11 .0290(10) .0230(10) .0280(10) -.0062(9) .0032(9) -.0003(9) C11' .0300(10) .0230(10) .0224(10) .0015(10) .0023(9) -.0040(8) C12 .0300(10) .0370(10) .0260(10) -.0040(10) .0054(10) .0028(10) C12' .0250(10) .0300(10) .0250(10) .0043(10) .0048(9) .0015(9) C13 .0290(10) .0290(10) .0240(10) .0036(10) .0003(9) -.0033(9) C13' .0260(10) .0280(10) .0320(10) .0004(10) .0018(10) .0067(9) C14 .0290(10) .0180(10) .0330(10) -.0012(9) -.0014(10) -.0029(9) C14' .0270(10) .0190(10) .0400(10) -.0021(10) -.0020(10) .0014(9) C15 .0230(10) .0190(10) .0330(10) -.0014(9) .0031(9) .0015(9) C15' .0290(10) .0180(10) .0340(10) .0019(9) .0021(10) -.0001(9) C16 .0260(10) .0150(10) .0234(10) -.0014(9) .0005(9) -.0023(8) C16' .0210(10) .0160(10) .0225(10) .0002(8) -.0019(8) -.0020(8) C17 .0270(10) .0200(10) .0310(10) .0022(9) .0034(9) .0009(9) C17' .0350(10) .0210(10) .0240(10) .0034(10) .0045(9) .0022(8) C18 .0260(10) .0260(10) .0400(10) .0060(10) .0050(10) -.0043(10) C18' .052(2) .0230(10) .0240(10) .0010(10) .0090(10) .0046(9) C19 .0300(10) .0190(10) .0490(10) .0066(10) .0000(10) .0010(10) C19' .052(2) .0190(10) .0280(10) -.0010(10) -.0010(10) .0048(9) C20 .0420(10) .0180(10) .0340(10) .0030(10) .0000(10) .0061(9) C20' .0360(10) .0210(10) .0330(10) .0090(10) .0015(10) .0009(9) C21 .0330(10) .0210(10) .0290(10) .0030(10) .0052(10) .0037(9) C21' .0320(10) .0210(10) .0240(10) .0041(10) .0048(9) .0009(8) C22 .0390(10) .0360(10) .0300(10) -.0130(10) .0030(10) -.0040(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .018 .009 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' H H .000 .000 International_Tables_Vol_C_Table_6.1.1.2_1992 N N .031 .018 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' O O .049 .032 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' Cl Cl .364 .702 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' 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 O2 O1 C2 107.20(10) yes O2' O1' C2' 107.70(10) yes O1 O2 H2o 102.5 yes O1' O2' H2o' 103.4 yes C1 N1 C2 106.0(2) no C1' N1' C2' 105.5(2) no C1 N2 C3 104.9(2) no C1' N2' C3' 104.8(2) no N1 C1 N2 116.5(2) no N1 C1 C4 125.2(2) no N2 C1 C4 118.3(2) no N1' C1' N2' 116.6(2) no N1' C1' C4' 124.9(2) no N2' C1' C4' 118.5(2) no O1 C2 N1 110.8(2) no O1 C2 C3 112.0(2) no O1 C2 C10 106.1(2) no N1 C2 C3 102.2(2) no N1 C2 C10 111.4(2) no C3 C2 C10 114.6(2) no O1' C2' N1' 111.9(2) no O1' C2' C3' 113.3(2) no O1' C2' C10' 106.0(2) no N1' C2' C3' 102.0(2) no N1' C2' C10' 108.1(2) no C3' C2' C10' 115.5(2) no N2 C3 C2 110.4(2) no N2 C3 C16 124.0(2) no C2 C3 C16 125.6(2) no N2' C3' C2' 110.9(2) no N2' C3' C16' 123.7(2) no C2' C3' C16' 125.4(2) no C1 C4 C5 120.4(2) no C1 C4 C9 119.8(2) no C5 C4 C9 119.8(2) no C1' C4' C5' 120.1(2) no C1' C4' C9' 120.0(2) no C5' C4' C9' 119.9(2) no C4 C5 C6 119.6(2) no C4 C5 H5 119.7 no C6 C5 H5 120.3 no C4' C5' C6' 119.4(2) no C4' C5' H5' 121.7 no C6' C5' H5' 118.0 no C5 C6 C7 120.6(2) no C5 C6 H6 120.0 no C7 C6 H6 119.3 no C5' C6' C7' 120.5(3) no C5' C6' H6' 118.9 no C7' C6' H6' 120.6 no C6 C7 C8 120.1(2) no C6 C7 H7 121.2 no C8 C7 H7 118.5 no C6' C7' C8' 120.2(2) no C6' C7' H7' 120.9 no C8' C7' H7' 118.9 no C7 C8 C9 119.7(2) no C7 C8 H8 120.0 no C9 C8 H8 120.2 no C7' C8' C9' 120.0(2) no C7' C8' H8' 122.6 no C9' C8' H8' 117.2 no C4 C9 C8 120.2(2) no C4 C9 H9 121.5 no C8 C9 H9 118.3 no C4' C9' C8' 120.0(2) no C4' C9' H9' 118.5 no C8' C9' H9' 121.3 no C2 C10 C11 119.9(2) no C2 C10 C15 120.1(2) no C11 C10 C15 120.0(2) no C2' C10' C11' 119.9(2) no C2' C10' C15' 120.5(2) no C11' C10' C15' 119.5(2) no C10 C11 C12 120.1(2) no C10 C11 H11 123.9 no C12 C11 H11 116.0 no C10' C11' C12' 120.4(2) no C10' C11' H11' 120.7 no C11' C12' H11' 118.9 no C11 C12 C13 120.0(2) no C11 C12 H12 119.2 no C13 C12 H12 120.8 no C11' C12' C13' 120.0(2) no C11' C12' H12' 119.0 no C13' C12' H12' 121.0 no C12 C13 C14 120.0(2) no C12 C13 H13 122.8 no C14 C13 H13 116.7 no C12' C13' C14' 119.6(2) no C12' C13' H13' 117.4 no C14' C13' H13' 122.9 no C13 C14 C15 120.0(2) no C13 C14 H14 120.9 no C15 C14 H14 119.1 no C13' C14' C15' 121.1(2) no C13' C14' H14' 116.6 no C15' C14' H14' 122.2 no C10 C15 C14 120.0(2) no C10 C15 H15 125.3 no C14 C15 H15 114.5 no C10' C15' C14' 119.4(2) no C10' C15' H15' 117.3 no C14' C15' H15' 123.2 no C3 C16 C17 121.2(2) no C3 C16 C21 119.3(2) no C17 C16 C21 119.4(2) no C3' C16' C17' 121.8(2) no C3' C16' C21' 119.2(2) no C17' C16' C21' 119.0(2) no C16 C17 C18 120.1(2) no C16 C17 H17 123.4 no C18 C17 H17 116.5 no C16' C17' C18' 120.1(2) no C16' C17' H17' 120.8 no C18' C17' H17' 119.0 no C17 C18 C19 120.0(2) no C17 C18 H18 118.8 no C19 C18 H18 121.1 no C17' C18' C19' 120.3(2) no C17' C18' H18' 117.4 no C19' C18' H18' 122.2 no C18 C19 C20 120.4(2) no C18 C19 H19 120.0 no C20 C19 H19 119.5 no C18' C19' C20' 120.1(2) no C18' C19' H19' 121.2 no C20' C19' H19' 118.7 no C19 C20 C21 120.2(2) no C19 C20 H20 118.0 no C21 C20 H20 120.8 no C19' C20' C21' 120.2(2) no C19' C20' H20' 123.6 no C21' C20' H20' 116.2 no C16 C21 C20 119.9(2) no C16 C21 H21 118.6 no C20 C21 H21 121.4 no C16' C21' C20' 120.3(2) no C16' C21' H21' 121.8 no C20' C21' H21' 117.9 no Cl1 C22 Cl2 111.00(10) no Cl1 C22 H22 108.1 no Cl1 C22 H22' 113.3 no Cl2 C22 H22 110.7 no Cl2 C22 H22' 104.1 no H22 C22 H22' 109.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C22 . . 1.754(3) no Cl2 C22 . . 1.747(3) no O1 O2 . . 1.470(2) yes O1 C2 . . 1.419(3) yes O1' O2' . . 1.464(2) yes O1' C2' . . 1.418(2) yes O2 H2o . . 1.001 no O2' H2o' . . 1.007 no N1 C1 . . 1.288(3) no N1 C2 . . 1.465(3) no N1' C1' . . 1.288(3) no N1' C2' . . 1.477(3) no N2 C1 . . 1.438(3) no N2 C3 . . 1.293(3) no N2' C1' . . 1.432(3) no N2' C3' . . 1.291(3) no C1 C4 . . 1.467(3) no C1' C4' . . 1.470(3) no C2 C3 . . 1.548(3) no C2 C10 . . 1.526(3) no C2' C3' . . 1.534(3) no C2' C10' . . 1.518(3) no C3 C16 . . 1.451(3) no C3' C16' . . 1.459(3) no C4 C5 . . 1.400(3) no C4 C9 . . 1.394(3) no C4' C5' . . 1.394(4) no C4' C9' . . 1.393(3) no C5 C6 . . 1.381(3) no C5 H5 . . .968 no C5' C6' . . 1.390(4) no C5' H5' . . .994 no C6 C7 . . 1.384(4) no C6 H6 . . .953 no C6' C7' . . 1.382(4) no C6' H6' . . .938 no C7 C8 . . 1.393(4) no C7 H7 . . 1.020 no C7' C8' . . 1.383(4) no C7' H7' . . 1.009 no C8 C9 . . 1.386(4) no C8 H8 . . 1.027 no C8' C9' . . 1.387(3) no C8' H8' . . 1.018 no C9 H9 . . .973 no C9' H9' . . 1.017 no C10 C11 . . 1.387(3) no C10 C15 . . 1.385(3) no C10' C11' . . 1.390(3) no C10' C15' . . 1.397(3) no C11 C12 . . 1.393(3) no C11 H11 . . .953 no C11' C12' . . 1.388(4) no C11' H11' . . .959 no C12 C13 . . 1.386(4) no C12 H12 . . .925 no C12' C13' . . 1.387(4) no C12' H12' . . .979 no C13 C14 . . 1.385(4) no C13 H13 . . .991 no C13' C14' . . 1.380(4) no C13' H13' . . .996 no C14 C15 . . 1.396(3) no C14 H14 . . .964 no C14' C15' . . 1.387(4) no C14' H14' . . .978 no C15 H15 . . .950 no C15' H15' . . 1.022 no C16 C17 . . 1.398(3) no C16 C21 . . 1.404(3) no C16' C17' . . 1.390(3) no C16' C21' . . 1.409(3) no C17 C18 . . 1.388(3) no C17 H17 . . .998 no C17' C18' . . 1.390(3) no C17' H17' . . 1.003 no C18 C19 . . 1.384(4) no C18 H18 . . .987 no C18' C19' . . 1.384(4) no C18' H18' . . .930 no C19 C20 . . 1.388(4) no C19 H19 . . .991 no C19' C20' . . 1.382(4) no C19' H19' . . .934 no C20 C21 . . 1.382(4) no C20 H20 . . .984 no C20' C21' . . 1.382(3) no C20' H20' . . .950 no C21 H21 . . 1.064 no C21' H21' . . .981 no C22 H22 . . .912 no C22 H22' . . 1.002 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O1' 3.282(2) . no O1 C12 3.296(3) 2_555 no O1' C12' 3.097(3) 2_555 no O2 N1' 2.773(2) . no O2 C22 3.035(3) 6_555 no O2' N1 2.760(2) . no N1 N1' 3.243(3) . no 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_publ_flag O2' H2o' N1 1.00 1.76 2.760(2) 173.60(10) yes O2 H2o N1' 1.01 1.77 2.773(2) 176.20(10) 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_publ_flag O1 C2 N1 C1 -119.0(2) no O1 C2 C3 N2 119.0(2) no O1 C2 C3 C16 -61.4(3) no O1 C2 C10 C11 -26.1(3) no O1 C2 C10 C15 155.5(2) no O1' C2' N1' C1' -125.0(2) no O1' C2' C3' N2' 123.4(2) no O1' C2' C3' C16' -58.1(3) no O1' C2' C10' C11' -38.0(2) no O1' C2' C10' C15' 145.3(2) no O2 O1 C2 N1 61.3(2) no O2 O1 C2 C3 -52.1(2) no O2 O1 C2 C10 -177.70(10) no O2' O1' C2' N1' 62.9(2) no O2' O1' C2' C3' -51.7(2) no O2' O1' C2' C10' -179.50(10) no N1 C1 N2 C3 1.4(3) no N1 C1 C4 C5 7.3(3) no N1 C1 C4 C9 -171.0(2) no N1 C2 C3 N2 .4(2) no N1 C2 C3 C16 179.9(2) no N1 C2 C10 C11 94.5(2) no N1 C2 C10 C15 -84.0(2) no N1' C1' N2' C3' -1.5(3) no N1' C1' C4' C5' 11.9(4) no N1' C1' C4' C9' -168.7(2) no N1' C2' C3' N2' 3.0(2) no N1' C2' C3' C16' -178.5(2) no N1' C2' C10' C11' 82.2(2) no N1' C2' C10' C15' -94.6(2) no N2 C1 N1 C2 -1.1(2) no N2 C1 C4 C5 -175.3(2) no N2 C1 C4 C9 6.4(3) no N2 C3 C2 C10 -120.2(2) no N2 C3 C16 C17 -179.0(2) no N2 C3 C16 C21 1.8(3) no N2' C1' N1' C2' 3.4(2) no N2' C1' C4' C5' -166.2(2) no N2' C1' C4' C9' 13.3(3) no N2' C3' C2' C10' -114.1(2) no N2' C3' C16' C17' 176.5(2) no N2' C3' C16' C21' -3.4(3) no C1 N1 C2 C3 .5(2) no C1 N1 C2 C10 123.2(2) no C1 N2 C3 C2 -.9(2) no C1 N2 C3 C16 179.5(2) no C1 C4 C5 C6 -178.6(2) no C1 C4 C5 H5 7.8(3) no C1 C4 C9 C8 178.1(2) no C1 C4 C9 H9 -2.8(4) no C1' N1' C2' C3' -3.6(2) no C1' N1' C2' C10' 118.7(2) no C1' N2' C3' C2' -1.2(2) no C1' N2' C3' C16' -179.7(2) no C1' C4' C5' C6' 178.5(3) no C1' C4' C5' H5' 10.0(5) no C1' C4' C9' C8' -179.0(2) no C1' C4' C9' H9' 6.1(4) no C2 O1 O2 H2o -90.2(2) no C2 N1 C1 C4 176.3(2) no C2 C3 C16 C17 1.5(3) no C2 C3 C16 C21 -177.7(2) no C2 C10 C11 C12 -179.8(2) no C2 C10 C11 H11 1.9(4) no C2 C10 C15 C14 179.0(2) no C2 C10 C15 H15 5.0(4) no C2' O1' O2' H2o' -90.6(2) no C2' N1' C1' C4' -174.7(2) no C2' C3' C16' C17' -1.8(3) no C2' C3' C16' C21' 178.2(2) no C2' C10' C11' C12' -176.9(2) no C2' C10' C11' H11' 2.5(3) no C2' C10' C15' C14' 176.3(2) no C2' C10' C15' H15' -6.4(3) no C3 N2 C1 C4 -176.3(2) no C3 C2 C10 C11 -150.1(2) no C3 C2 C10 C15 31.4(3) no C3 C16 C17 C18 -177.9(2) no C3 C16 C17 H17 .5(4) no C3 C16 C21 C20 178.4(2) no C3 C16 C21 H21 -1.2(3) no C3' N2' C1' C4' 176.7(2) no C3' C2' C10' C11' -164.3(2) no C3' C2' C10' C15' 19.0(3) no C3' C16' C17' C18' -178.3(2) no C3' C16' C17' H17' -.7(4) no C3' C16' C21' C20' 179.0(2) no C3' C16' C21' H21' .4(3) no C4 C5 C6 C7 .6(4) no C4 C5 C6 H6 -176.0(2) no C4 C9 C8 C7 .5(4) no C4 C9 C8 H8 177.7(2) no C4' C5' C6' C7' .7(5) no C4' C5' C6' H6' -180.0(3) no C4' C9' C8' C7' .3(4) no C4' C9' C8' H8' 176.3(2) no C5 C4 C9 C8 -.2(4) no C5 C4 C9 H9 178.8(2) no C5 C6 C7 C8 -.3(4) no C5 C6 C7 H7 -176.0(2) no C5' C4' C9' C8' .4(4) no C5' C4' C9' H9' -174.5(3) no C5' C6' C7' C8' -.1(5) no C5' C6' C7' H7' 179.1(3) no C6 C5 C4 C9 -.3(3) no C6 C7 C8 C9 -.3(4) no C6 C7 C8 H8 -177.5(3) no C6' C5' C4' C9' -.9(4) no C6' C7' C8' C9' -.4(5) no C6' C7' C8' H8' -176.3(3) no C7 C6 C5 H5 174.1(2) no C7 C8 C9 H9 -178.6(3) no C7' C6' C5' H5' 169.8(3) no C7' C8' C9' H9' 175.0(3) no C8 C7 C6 H6 176.3(3) no C8' C7' C6' H6' -179.4(3) no C9 C4 C5 H5 -173.9(2) no C9 C8 C7 H7 175.5(3) no C9' C4' C5' H5' -169.5(3) no C9' C8' C7' H7' -179.6(3) no C10 C2 C3 C16 59.4(3) no C10 C11 C12 C13 1.1(4) no C10 C11 C12 H12 -177.8(2) no C10 C15 C14 C13 .5(3) no C10 C15 C14 H14 -179.0(2) no C10' C2' C3' C16' 64.5(3) no C10' C11' C12' C13' .3(3) no C10' C11' C12' H12' 179.6(2) no C10' C15' C14' C13' .7(4) no C10' C15' C14' H14' -176.6(2) no C11 C10 C15 C14 .5(3) no C11 C10 C15 H15 -173.5(2) no C11 C12 C13 C14 -.2(4) no C11 C12 C13 H13 171.4(2) no C11' C10' C15' C14' -.4(3) no C11' C10' C15' H15' 176.9(2) no C11' C12' C13' C14' .0(3) no C11' C12' C13' H13' -175.7(2) no C12 C11 C10 C15 -1.3(4) no C12 C13 C14 C15 -.6(4) no C12 C13 C14 H14 178.8(2) no C11' C12' C10' C15' -.1(3) no C12' C13' C14' C15' -.5(4) no C12' C13' C14' H14' 176.9(2) no C13 C12 C11 H11 179.6(2) no C13 C14 C15 H15 175.1(2) no C13' C12' C11' H11' -179.1(2) no C13' C14' C15' H15' -176.4(2) no C14 C13 C12 H12 178.8(3) no C14' C13' C12' H12' -179.2(2) no C15 C10 C11 H11 -179.6(2) no C15 C14 C13 H13 -172.7(2) no C15' C10' C11' H11' 179.3(2) no C15' C14' C13' H13' 175.0(2) no C16 C17 C18 C19 -.6(4) no C16 C17 C18 H18 176.2(2) no C16 C21 C20 C19 -.3(4) no C16 C21 C20 H20 167.5(2) no C16' C17' C18' C19' -1.2(4) no C16' C17' C18' H18' -178.6(2) no C16' C21' C20' C19' -.2(4) no C16' C21' C20' H20' -177.8(2) no C17 C16 C21 C20 -.9(3) no C17 C16 C21 H21 179.5(2) no C17 C18 C19 C20 -.6(4) no C17 C18 C19 H19 -178.1(2) no C17' C16' C21' C20' -1.0(3) no C17' C16' C21' H21' -179.5(2) no C17' C18' C19' C20' .0(4) no C17' C18' C19' H19' 178.1(3) no C18 C17 C16 C21 1.3(3) no C18 C19 C20 C21 1.1(4) no C18 C19 C20 H20 -167.1(2) no C18' C17' C16' C21' 1.7(3) no C18' C19' C20' C21' .7(4) no C18' C19' C20' H20' 178.1(3) no C19 C18 C17 H17 -179.1(2) no C19 C20 C21 H21 179.2(2) no C19' C18' C17' H17' -178.9(2) no C19' C20' C21' H21' 178.4(2) no C20 C19 C18 H18 -177.3(2) no C20' C19' C18' H18' 177.3(3) no C21 C16 C17 H17 179.7(2) no C21 C20 C19 H19 178.6(2) no C21' C16' C17' H17' 179.3(2) no C21' C20' C19' H19' -177.4(2) no H5 C5 C6 H6 -2.5(4) no H5' C5' C6' H6' -10.9(6) no H6 C6 C7 H7 .6(4) no H6' C6' C7' H7' -.2(6) no H7 C7 C8 H8 -1.7(4) no H7' C7' C8' H8' 4.5(5) no H8 C8 C9 H9 -1.4(4) no H8' C8' C9' H9' -9.0(4) no H11 C11 C12 H12 .6(4) no H11' C11' C12' H12' .2(4) no H12 C12 C13 H13 -9.7(4) no H12' C12' C13' H13' 5.0(4) no H13 C13 C14 H14 6.8(4) no H13' C13' C14' H14' -7.6(4) no H14 C14 C15 H15 -4.4(4) no H14' C14' C15' H15' 6.3(4) no H17 C17 C18 H18 -2.3(4) no H17' C17' C18' H18' 3.8(4) no H18 C18 C19 H19 5.2(4) no H18' C18' C19' H19' -4.7(5) no H19 C19 C20 H20 10.4(4) no H19' C19' C20' H20' .0(5) no H20 C20 C21 H21 -12.9(4) no H20' C20' C21' H21' .8(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139057976