#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206763.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_2206763 loop_ _publ_author_name 'Zhao, Jun-Feng' 'Hu, Yang-Gen' 'Ding, Ming-Wu' 'He, Hong-Wu' _publ_section_title ; 5,6-Dianilino-3-(4-chlorophenyl)-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin-7-one ; _journal_coeditor_code OB6548 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2791 _journal_page_last o2792 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H16 Cl N7 O' _chemical_formula_moiety 'C22 H16 Cl N7 O' _chemical_formula_sum 'C22 H16 Cl N7 O' _chemical_formula_weight 429.87 _chemical_melting_point 512 _chemical_name_systematic ; 5,6-Dianilino-3-(4-chlorophenyl)-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin- 7-one ; _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 90.0010(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.981(2) _cell_length_b 7.6973(12) _cell_length_c 17.468(3) _cell_measurement_reflns_used 2384 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 21.99 _cell_measurement_theta_min 2.89 _cell_volume 2014.3(5) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12017 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.79 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.425 _refine_diff_density_min -0.368 _refine_ls_extinction_coef 0.00050(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 4395 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.901 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0497 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0602P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1112 _refine_ls_wR_factor_ref 0.1250 _reflns_number_gt 2595 _reflns_number_total 4395 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6548.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_cif_authors_sg_Hall '-P 2yn ' _cod_database_code 2206763 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_type_symbol C1 0.38608(16) -0.0134(3) 0.40410(13) 0.0660(7) Uani d . 1 C H1 0.3356 0.0482 0.4191 0.079 Uiso calc R 1 H C2 0.42405(17) 0.0163(3) 0.33326(14) 0.0700(7) Uani d . 1 C H2 0.3994 0.0992 0.3008 0.084 Uiso calc R 1 H C3 0.49758(16) -0.0753(3) 0.31059(12) 0.0553(6) Uani d . 1 C C4 0.53438(14) -0.1995(3) 0.35809(12) 0.0574(6) Uani d . 1 C H4 0.5839 -0.2629 0.3423 0.069 Uiso calc R 1 H C5 0.49713(14) -0.2288(3) 0.42927(12) 0.0529(5) Uani d . 1 C H5 0.5217 -0.3118 0.4617 0.063 Uiso calc R 1 H C6 0.42330(13) -0.1347(3) 0.45223(11) 0.0458(5) Uani d . 1 C C7 0.31902(13) -0.0782(2) 0.56385(11) 0.0428(5) Uani d . 1 C C8 0.30472(13) -0.1735(2) 0.62912(10) 0.0435(5) Uani d . 1 C C9 0.23816(13) -0.1207(3) 0.68341(11) 0.0461(5) Uani d . 1 C C10 0.22188(13) 0.1289(3) 0.59387(11) 0.0431(5) Uani d . 1 C C11 0.18987(15) 0.4089(2) 0.52738(11) 0.0474(5) Uani d . 1 C C12 0.12057(17) 0.5253(3) 0.51824(13) 0.0639(6) Uani d . 1 C H12 0.0709 0.5199 0.5501 0.077 Uiso calc R 1 H C13 0.12552(19) 0.6501(3) 0.46131(15) 0.0794(8) Uani d . 1 C H13 0.0791 0.7293 0.4556 0.095 Uiso calc R 1 H C14 0.1977(2) 0.6588(3) 0.41336(15) 0.0818(8) Uani d . 1 C H14 0.1994 0.7401 0.3740 0.098 Uiso calc R 1 H C15 0.2674(2) 0.5456(3) 0.42422(15) 0.0762(8) Uani d . 1 C H15 0.3176 0.5532 0.3930 0.091 Uiso calc R 1 H C16 0.26413(16) 0.4206(3) 0.48093(13) 0.0605(6) Uani d . 1 C H16 0.3118 0.3447 0.4878 0.073 Uiso calc R 1 H C17 0.03856(13) 0.0183(2) 0.68339(11) 0.0441(5) Uani d . 1 C C18 -0.02896(15) 0.0324(3) 0.73664(13) 0.0602(6) Uani d . 1 C H18 -0.0183 0.0867 0.7833 0.072 Uiso calc R 1 H C19 -0.11271(17) -0.0346(4) 0.72046(17) 0.0778(8) Uani d . 1 C H19 -0.1582 -0.0257 0.7564 0.093 Uiso calc R 1 H C20 -0.12868(17) -0.1141(4) 0.65144(17) 0.0796(8) Uani d . 1 C H20 -0.1846 -0.1612 0.6410 0.095 Uiso calc R 1 H C21 -0.06210(18) -0.1238(3) 0.59810(15) 0.0725(7) Uani d . 1 C H21 -0.0735 -0.1751 0.5509 0.087 Uiso calc R 1 H C22 0.02157(15) -0.0587(3) 0.61338(12) 0.0572(6) Uani d . 1 C H22 0.0665 -0.0664 0.5768 0.069 Uiso calc R 1 H Cl1 0.54410(5) -0.03631(9) 0.22126(4) 0.0831(3) Uani d . 1 Cl N1 0.38419(10) -0.1658(2) 0.52542(9) 0.0449(4) Uani d . 1 N N2 0.40903(12) -0.3101(2) 0.56786(9) 0.0542(5) Uani d . 1 N N3 0.36098(11) -0.3130(2) 0.63005(9) 0.0526(5) Uani d . 1 N N4 0.28118(11) 0.0749(2) 0.54387(9) 0.0450(4) Uani d . 1 N N5 0.19470(10) 0.0323(2) 0.65726(9) 0.0430(4) Uani d . 1 N N6 0.18025(11) 0.2832(2) 0.58623(9) 0.0514(4) Uani d . 1 N H6 0.1428 0.3090 0.6218 0.062 Uiso calc R 1 H N7 0.12268(11) 0.0947(2) 0.69985(9) 0.0471(4) Uani d . 1 N H7 0.1289 0.1744 0.7339 0.057 Uiso calc R 1 H O1 0.21644(9) -0.1877(2) 0.74336(8) 0.0596(4) Uani d . 1 O 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 C1 0.0724(16) 0.0689(15) 0.0566(14) 0.0251(13) 0.0151(12) 0.0129(12) C2 0.0919(19) 0.0628(16) 0.0552(14) 0.0149(14) 0.0136(13) 0.0148(12) C3 0.0644(15) 0.0531(13) 0.0485(12) -0.0117(11) 0.0151(11) -0.0062(10) C4 0.0509(13) 0.0652(15) 0.0561(13) -0.0002(11) 0.0074(11) -0.0123(12) C5 0.0490(13) 0.0595(14) 0.0501(13) 0.0059(11) -0.0011(10) -0.0013(10) C6 0.0486(12) 0.0471(12) 0.0417(11) 0.0012(10) 0.0015(9) -0.0023(9) C7 0.0414(11) 0.0460(12) 0.0410(11) 0.0013(9) -0.0030(9) -0.0003(9) C8 0.0440(12) 0.0450(12) 0.0416(11) 0.0042(9) -0.0042(9) 0.0029(9) C9 0.0449(12) 0.0509(12) 0.0426(12) -0.0025(10) -0.0072(10) 0.0025(10) C10 0.0457(12) 0.0434(12) 0.0402(11) 0.0007(9) -0.0059(9) -0.0017(9) C11 0.0605(14) 0.0367(11) 0.0450(12) -0.0012(10) -0.0041(10) -0.0017(9) C12 0.0793(17) 0.0524(14) 0.0601(14) 0.0169(12) -0.0004(12) 0.0033(11) C13 0.100(2) 0.0584(16) 0.0801(19) 0.0213(15) -0.0128(17) 0.0084(14) C14 0.123(3) 0.0539(16) 0.0684(17) -0.0027(17) -0.0027(17) 0.0129(13) C15 0.097(2) 0.0550(15) 0.0763(18) -0.0106(15) 0.0096(15) 0.0072(13) C16 0.0673(16) 0.0458(13) 0.0683(15) -0.0021(11) 0.0006(12) 0.0057(11) C17 0.0469(12) 0.0400(11) 0.0453(12) 0.0037(9) -0.0035(10) 0.0005(9) C18 0.0558(15) 0.0733(16) 0.0514(13) 0.0028(12) 0.0022(11) -0.0032(11) C19 0.0509(16) 0.101(2) 0.0818(19) 0.0005(14) 0.0065(13) 0.0108(16) C20 0.0591(17) 0.0811(19) 0.099(2) -0.0111(14) -0.0200(17) 0.0052(16) C21 0.0714(18) 0.0693(17) 0.0770(18) -0.0046(14) -0.0246(15) -0.0133(13) C22 0.0582(14) 0.0591(14) 0.0542(13) 0.0031(11) -0.0071(11) -0.0111(11) Cl1 0.1107(6) 0.0774(5) 0.0611(4) -0.0119(4) 0.0326(4) -0.0002(3) N1 0.0459(10) 0.0459(10) 0.0430(9) 0.0080(8) 0.0008(8) 0.0046(8) N2 0.0587(11) 0.0540(11) 0.0498(10) 0.0127(9) -0.0008(9) 0.0072(9) N3 0.0563(11) 0.0545(11) 0.0470(10) 0.0105(9) -0.0017(9) 0.0084(8) N4 0.0477(10) 0.0436(10) 0.0436(9) 0.0075(8) 0.0015(8) 0.0033(7) N5 0.0456(10) 0.0454(10) 0.0381(9) 0.0027(8) 0.0012(7) -0.0012(7) N6 0.0600(11) 0.0460(10) 0.0481(10) 0.0114(9) 0.0056(8) 0.0011(8) N7 0.0487(10) 0.0482(10) 0.0444(9) -0.0002(8) 0.0028(8) -0.0136(8) O1 0.0608(10) 0.0694(10) 0.0486(9) 0.0056(8) 0.0073(7) 0.0144(8) 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' Cl Cl 0.1484 0.1585 '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 C6 C1 C2 119.6(2) ? C6 C1 H1 120.2 ? C2 C1 H1 120.2 ? C3 C2 C1 120.4(2) ? C3 C2 H2 119.8 ? C1 C2 H2 119.8 ? C2 C3 C4 120.3(2) ? C2 C3 Cl1 119.68(19) ? C4 C3 Cl1 119.99(18) ? C3 C4 C5 119.5(2) ? C3 C4 H4 120.2 ? C5 C4 H4 120.2 ? C4 C5 C6 119.9(2) ? C4 C5 H5 120.0 ? C6 C5 H5 120.0 ? C1 C6 C5 120.2(2) ? C1 C6 N1 119.71(18) ? C5 C6 N1 120.07(18) ? N4 C7 N1 127.13(17) ? N4 C7 C8 127.89(18) ? N1 C7 C8 104.86(17) ? N3 C8 C7 109.50(18) ? N3 C8 C9 130.11(18) ? C7 C8 C9 120.40(18) ? O1 C9 N5 120.50(19) ? O1 C9 C8 129.57(19) ? N5 C9 C8 109.93(17) ? N4 C10 N6 121.75(18) ? N4 C10 N5 123.80(18) ? N6 C10 N5 114.42(18) ? C16 C11 C12 119.7(2) ? C16 C11 N6 123.53(19) ? C12 C11 N6 116.7(2) ? C11 C12 C13 119.5(2) ? C11 C12 H12 120.2 ? C13 C12 H12 120.2 ? C14 C13 C12 121.0(2) ? C14 C13 H13 119.5 ? C12 C13 H13 119.5 ? C13 C14 C15 119.0(2) ? C13 C14 H14 120.5 ? C15 C14 H14 120.5 ? C14 C15 C16 120.9(3) ? C14 C15 H15 119.6 ? C16 C15 H15 119.6 ? C11 C16 C15 119.7(2) ? C11 C16 H16 120.1 ? C15 C16 H16 120.1 ? C18 C17 C22 119.7(2) ? C18 C17 N7 118.83(18) ? C22 C17 N7 121.33(19) ? C17 C18 C19 119.8(2) ? C17 C18 H18 120.1 ? C19 C18 H18 120.1 ? C20 C19 C18 120.2(3) ? C20 C19 H19 119.9 ? C18 C19 H19 119.9 ? C21 C20 C19 119.7(2) ? C21 C20 H20 120.1 ? C19 C20 H20 120.1 ? C20 C21 C22 120.8(2) ? C20 C21 H21 119.6 ? C22 C21 H21 119.6 ? C21 C22 C17 119.7(2) ? C21 C22 H22 120.1 ? C17 C22 H22 120.1 ? C7 N1 N2 108.98(15) yes C7 N1 C6 130.72(16) yes N2 N1 C6 120.23(16) yes N3 N2 N1 108.11(15) ? N2 N3 C8 108.55(16) ? C10 N4 C7 112.81(16) ? C10 N5 N7 117.73(16) ? C10 N5 C9 124.29(17) ? N7 N5 C9 117.90(15) ? C10 N6 C11 128.70(18) ? C10 N6 H6 115.6 ? C11 N6 H6 115.6 ? N5 N7 C17 115.84(15) ? N5 N7 H7 122.1 ? C17 N7 H7 122.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 1.374(3) ? C1 C2 1.381(3) ? C1 H1 0.9300 ? C2 C3 1.367(3) ? C2 H2 0.9300 ? C3 C4 1.381(3) ? C3 Cl1 1.735(2) ? C4 C5 1.382(3) ? C4 H4 0.9300 ? C5 C6 1.382(3) ? C5 H5 0.9300 ? C6 N1 1.426(2) ? C7 N4 1.353(2) yes C7 N1 1.363(2) yes C7 C8 1.373(3) yes C8 N3 1.365(2) yes C8 C9 1.435(3) yes C9 O1 1.212(2) yes C9 N5 1.421(2) yes C10 N4 1.313(2) yes C10 N6 1.348(2) ? C10 N5 1.395(2) yes C11 C16 1.380(3) ? C11 C12 1.381(3) ? C11 N6 1.419(2) ? C12 C13 1.385(3) ? C12 H12 0.9300 ? C13 C14 1.369(3) ? C13 H13 0.9300 ? C14 C15 1.374(4) ? C14 H14 0.9300 ? C15 C16 1.382(3) ? C15 H15 0.9300 ? C16 H16 0.9300 ? C17 C18 1.379(3) ? C17 C22 1.383(3) ? C17 N7 1.420(2) ? C18 C19 1.386(3) ? C18 H18 0.9300 ? C19 C20 1.373(4) ? C19 H19 0.9300 ? C20 C21 1.367(3) ? C20 H20 0.9300 ? C21 C22 1.376(3) ? C21 H21 0.9300 ? C22 H22 0.9300 ? N1 N2 1.386(2) yes N2 N3 1.303(2) yes N5 N7 1.396(2) ? N6 H6 0.8600 ? N7 H7 0.8600 ? 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 _geom_hbond_publ_flag N6 H6 N7 . 0.86 2.16 2.606(2) 112 yes N7 H7 N3 2_556 0.86 2.38 3.065(2) 137 yes N7 H7 O1 2_556 0.86 2.58 3.098(2) 120 yes C1 H1 N4 . 0.93 2.34 2.982(3) 126 no C5 H5 N2 . 0.93 2.51 2.827(3) 100 no C16 H16 N4 . 0.93 2.34 2.891(3) 118 no 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 C6 C1 C2 C3 0.7(4) C1 C2 C3 C4 0.4(4) C1 C2 C3 Cl1 179.83(19) C2 C3 C4 C5 -1.0(3) Cl1 C3 C4 C5 179.63(16) C3 C4 C5 C6 0.3(3) C2 C1 C6 C5 -1.3(3) C2 C1 C6 N1 -180.0(2) C4 C5 C6 C1 0.8(3) C4 C5 C6 N1 179.42(17) N4 C7 C8 N3 -175.33(17) N1 C7 C8 N3 0.9(2) N4 C7 C8 C9 5.0(3) N1 C7 C8 C9 -178.79(16) N3 C8 C9 O1 0.3(4) C7 C8 C9 O1 179.94(19) N3 C8 C9 N5 -178.88(18) C7 C8 C9 N5 0.7(2) C16 C11 C12 C13 1.5(3) N6 C11 C12 C13 -179.4(2) C11 C12 C13 C14 0.7(4) C12 C13 C14 C15 -2.5(4) C13 C14 C15 C16 2.2(4) C12 C11 C16 C15 -1.8(3) N6 C11 C16 C15 179.10(19) C14 C15 C16 C11 0.0(4) C22 C17 C18 C19 1.6(3) N7 C17 C18 C19 177.3(2) C17 C18 C19 C20 -0.3(4) C18 C19 C20 C21 -1.3(4) C19 C20 C21 C22 1.6(4) C20 C21 C22 C17 -0.3(4) C18 C17 C22 C21 -1.3(3) N7 C17 C22 C21 -176.85(19) N4 C7 N1 N2 175.54(17) C8 C7 N1 N2 -0.7(2) N4 C7 N1 C6 -7.5(3) C8 C7 N1 C6 176.20(17) C1 C6 N1 C7 -9.8(3) C5 C6 N1 C7 171.53(19) C1 C6 N1 N2 166.80(19) C5 C6 N1 N2 -11.8(3) C7 N1 N2 N3 0.3(2) C6 N1 N2 N3 -177.00(16) N1 N2 N3 C8 0.3(2) C7 C8 N3 N2 -0.7(2) C9 C8 N3 N2 178.91(19) N6 C10 N4 C7 176.47(16) N5 C10 N4 C7 -5.4(3) N1 C7 N4 C10 -178.09(18) C8 C7 N4 C10 -2.7(3) N4 C10 N5 N7 -171.47(16) N6 C10 N5 N7 6.8(2) N4 C10 N5 C9 11.7(3) N6 C10 N5 C9 -170.05(16) O1 C9 N5 C10 172.35(17) C8 C9 N5 C10 -8.4(2) O1 C9 N5 N7 -4.5(3) C8 C9 N5 N7 174.82(15) N4 C10 N6 C11 0.7(3) N5 C10 N6 C11 -177.63(17) C16 C11 N6 C10 -22.1(3) C12 C11 N6 C10 158.80(19) C10 N5 N7 C17 98.39(19) C9 N5 N7 C17 -84.6(2) C18 C17 N7 N5 160.60(17) C22 C17 N7 N5 -23.9(3)