#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203236.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_2203236 loop_ _publ_author_name 'Bao, Feng' 'L\"u, Xingqiang' 'Wu, Qing' 'Kang, Beisheng' 'Ng, Seik Weng' _publ_section_title 5-Methyl-2-phenyl-4-[(Z)-(2-tolylamino)phenylmethylene]pyrazol-3(2H)-one _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o155 _journal_page_last o156 _journal_paper_doi 10.1107/S1600536803029258 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C24 H21 N3 O' _chemical_formula_moiety 'C24 H21 N3 O' _chemical_formula_sum 'C24 H21 N3 O' _chemical_formula_weight 367.44 _chemical_name_systematic ; 5-Methyl-2-phenyl-4-[(Z)-(2-tolylamino)phenylmethylene]pyrazol-3(2H)-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 101.560(2) _cell_angle_beta 99.974(2) _cell_angle_gamma 108.034(2) _cell_formula_units_Z 2 _cell_length_a 9.7920(10) _cell_length_b 9.8320(10) _cell_length_c 11.556(2) _cell_measurement_reflns_used 848 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.5 _cell_measurement_theta_min 2.5 _cell_volume 1002.8(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _diffrn_measurement_device_type 'Bruker SMART 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 0.012 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8614 _diffrn_reflns_theta_full 27.1 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 1.86 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.15 _refine_diff_density_min -0.14 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4346 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.043 _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^)+(0.0626P)^2^+0.1426P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.114 _refine_ls_wR_factor_ref 0.133 _reflns_number_gt 2832 _reflns_number_total 4346 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wk6006.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1002.9(2) _cod_database_code 2203236 _cod_database_fobs_code 2203236 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_type_symbol O1 0.69740(10) 0.65410(10) 0.49370(10) 0.0671(3) Uani d . 1 O N1 0.85130(10) 0.80870(10) 0.68380(10) 0.0587(3) Uani d . 1 N N2 1.00300(10) 0.8909(2) 0.73320(10) 0.0660(4) Uani d . 1 N N3 0.8634(2) 0.6158(2) 0.33550(10) 0.0633(4) Uani d D 1 N C1 0.7521(2) 0.8179(2) 0.75850(10) 0.0581(4) Uani d . 1 C C2 0.8022(2) 0.9241(2) 0.8695(2) 0.0707(5) Uani d . 1 C C3 0.7046(2) 0.9353(2) 0.9410(2) 0.0852(6) Uani d . 1 C C4 0.5601(2) 0.8440(3) 0.9044(2) 0.0868(6) Uani d . 1 C C5 0.5114(2) 0.7390(2) 0.7945(2) 0.0884(6) Uani d . 1 C C6 0.6061(2) 0.7234(2) 0.7212(2) 0.0778(5) Uani d . 1 C C7 0.8215(2) 0.7327(2) 0.56320(10) 0.0535(4) Uani d . 1 C C8 0.9650(2) 0.7643(2) 0.53700(10) 0.0527(4) Uani d . 1 C C9 1.0685(2) 0.8640(2) 0.6471(2) 0.0603(4) Uani d . 1 C C10 1.2334(2) 0.9366(2) 0.6729(2) 0.0914(6) Uani d . 1 C C11 0.9832(2) 0.7019(2) 0.42440(10) 0.0506(3) Uani d . 1 C C12 1.1329(2) 0.7298(2) 0.40110(10) 0.0509(3) Uani d . 1 C C13 1.1910(2) 0.8400(2) 0.3475(2) 0.0655(4) Uani d . 1 C C14 1.3332(2) 0.8700(2) 0.3322(2) 0.0812(5) Uani d . 1 C C15 1.4147(2) 0.7884(2) 0.3678(2) 0.0819(6) Uani d . 1 C C16 1.3573(2) 0.6774(2) 0.4196(2) 0.0795(5) Uani d . 1 C C17 1.2171(2) 0.6493(2) 0.4376(2) 0.0676(4) Uani d . 1 C C18 0.8563(2) 0.5327(2) 0.21680(10) 0.0604(4) Uani d . 1 C C19 0.9211(2) 0.4264(2) 0.2043(2) 0.0755(5) Uani d . 1 C C20 0.9094(3) 0.3416(3) 0.0913(2) 0.1009(7) Uani d . 1 C C21 0.8326(3) 0.3614(3) -0.0081(2) 0.1103(8) Uani d . 1 C C22 0.7658(3) 0.4644(3) 0.0019(2) 0.1074(8) Uani d . 1 C C23 0.7766(2) 0.5548(2) 0.1169(2) 0.0829(5) Uani d . 1 C C24 0.7038(4) 0.6685(4) 0.1313(3) 0.1470(10) Uani d . 1 C H3n 0.7810(10) 0.610(2) 0.357(2) 0.087(6) Uiso d D 1 H H2 0.9009 0.9876 0.8961 0.085 Uiso calc R 1 H H3 0.7387 1.0070 1.0157 0.102 Uiso calc R 1 H H4 0.4955 0.8527 0.9532 0.104 Uiso calc R 1 H H5 0.4123 0.6766 0.7684 0.106 Uiso calc R 1 H H6 0.5716 0.6498 0.6475 0.093 Uiso calc R 1 H H10a 1.2569 0.9962 0.6176 0.137 Uiso calc R 1 H H10b 1.2774 0.8617 0.6622 0.137 Uiso calc R 1 H H10c 1.2718 0.9986 0.7554 0.137 Uiso calc R 1 H H13 1.1348 0.8942 0.3217 0.079 Uiso calc R 1 H H14 1.3734 0.9459 0.2976 0.097 Uiso calc R 1 H H15 1.5100 0.8085 0.3566 0.098 Uiso calc R 1 H H16 1.4127 0.6212 0.4426 0.095 Uiso calc R 1 H H17 1.1788 0.5754 0.4748 0.081 Uiso calc R 1 H H19 0.9732 0.4122 0.2734 0.091 Uiso calc R 1 H H20 0.9543 0.2707 0.0832 0.121 Uiso calc R 1 H H21 0.8248 0.3038 -0.0850 0.132 Uiso calc R 1 H H22 0.7122 0.4752 -0.0682 0.129 Uiso calc R 1 H H24a 0.6284 0.6408 0.1743 0.220 Uiso calc R 1 H H24b 0.6595 0.6738 0.0522 0.220 Uiso calc R 1 H H24c 0.7768 0.7637 0.1766 0.220 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 O1 0.0431(6) 0.0806(8) 0.0691(7) 0.0190(5) 0.0118(5) 0.0092(6) N1 0.0472(7) 0.0632(8) 0.0622(8) 0.0178(6) 0.0167(6) 0.0099(6) N2 0.0506(7) 0.0701(9) 0.0672(8) 0.0150(6) 0.0149(6) 0.0067(7) N3 0.0462(7) 0.0766(9) 0.0609(8) 0.0192(7) 0.0137(6) 0.0090(7) C1 0.0580(10) 0.0620(10) 0.0640(10) 0.0260(10) 0.0230(10) 0.0220(10) C2 0.0730(10) 0.0760(10) 0.0650(10) 0.0260(10) 0.0250(10) 0.0180(10) C3 0.100(2) 0.0910(10) 0.0740(10) 0.0370(10) 0.0420(10) 0.0200(10) C4 0.094(2) 0.100(2) 0.093(2) 0.0450(10) 0.0560(10) 0.0370(10) C5 0.0670(10) 0.099(2) 0.103(2) 0.0230(10) 0.0410(10) 0.0280(10) C6 0.0630(10) 0.0830(10) 0.0830(10) 0.0190(10) 0.0310(10) 0.0130(10) C7 0.0470(10) 0.0540(10) 0.0610(10) 0.0190(10) 0.0130(10) 0.0140(10) C8 0.0450(10) 0.0520(10) 0.0600(10) 0.0180(10) 0.0150(10) 0.0140(10) C9 0.0470(10) 0.0590(10) 0.0680(10) 0.0140(10) 0.0150(10) 0.0100(10) C10 0.0530(10) 0.0990(10) 0.0880(10) 0.0030(10) 0.0170(10) -0.0100(10) C11 0.0470(10) 0.0480(10) 0.0600(10) 0.0190(10) 0.0140(10) 0.0180(10) C12 0.0470(10) 0.0500(10) 0.0560(10) 0.0160(10) 0.0150(10) 0.0130(10) C13 0.0610(10) 0.0660(10) 0.0750(10) 0.0210(10) 0.0210(10) 0.0300(10) C14 0.0660(10) 0.0850(10) 0.0940(10) 0.0130(10) 0.0340(10) 0.0390(10) C15 0.0500(10) 0.0930(10) 0.0960(10) 0.0160(10) 0.0280(10) 0.0180(10) C16 0.0550(10) 0.0810(10) 0.109(2) 0.0330(10) 0.0220(10) 0.0250(10) C17 0.0550(10) 0.0660(10) 0.0920(10) 0.0250(10) 0.0230(10) 0.0330(10) C18 0.0520(10) 0.0620(10) 0.0580(10) 0.0100(10) 0.0150(10) 0.0130(10) C19 0.0740(10) 0.0710(10) 0.0770(10) 0.0240(10) 0.0200(10) 0.0110(10) C20 0.099(2) 0.088(2) 0.098(2) 0.0250(10) 0.0310(10) -0.0060(10) C21 0.110(2) 0.114(2) 0.076(2) 0.014(2) 0.0310(10) -0.0040(10) C22 0.106(2) 0.123(2) 0.0660(10) 0.014(2) 0.0020(10) 0.0260(10) C23 0.0790(10) 0.0880(10) 0.0720(10) 0.0200(10) 0.0070(10) 0.0250(10) C24 0.167(3) 0.151(3) 0.130(2) 0.091(2) -0.012(2) 0.041(2) 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 N2 N1 C7 111.90(10) yes N2 N1 C1 118.60(10) yes C1 N1 C7 129.50(10) yes N1 N2 C9 106.50(10) yes C11 N3 C18 128.30(10) yes N1 C1 C2 119.5(2) yes N1 C1 C6 120.9(2) yes C2 C1 C6 119.6(2) yes C3 C2 C1 119.5(2) yes C4 C3 C2 121.4(2) yes C3 C4 C5 118.8(2) yes C4 C5 C6 121.5(2) yes C1 C6 C5 119.3(2) yes O1 C7 N1 127.00(10) yes O1 C7 C8 128.50(10) yes N1 C7 C8 104.50(10) yes C7 C8 C9 105.30(10) yes C7 C8 C11 122.40(10) yes C9 C8 C11 132.30(10) yes N2 C9 C8 111.80(10) yes N2 C9 C10 119.0(2) yes C8 C9 C10 129.2(2) yes N3 C11 C8 118.90(10) yes N3 C11 C12 119.50(10) yes C8 C11 C12 121.60(10) yes C13 C12 C17 119.40(10) no C11 C12 C13 120.30(10) no C11 C12 C17 120.20(10) no C12 C13 C14 119.8(2) no C13 C14 C15 120.2(2) no C14 C15 C16 120.5(2) no C15 C16 C17 119.6(2) no C12 C17 C17 120.5(2) no C19 C18 C23 121.2(2) no N3 C18 C23 118.6(2) yes N3 C18 C19 120.1(2) yes C18 C19 C20 120.6(2) no C19 C20 C21 119.5(2) no C20 C21 C22 121.1(2) no C21 C22 C23 121.0(2) no C18 C23 C22 116.6(2) no C18 C23 C24 120.9(2) no C22 C23 C24 122.4(2) no C11 N3 H3n 113.0(10) no C18 N3 H3n 119.0(10) no C3 C2 H2 120.3 no C1 C2 H2 120.3 no C4 C3 H3 119.3 no C2 C3 H3 119.3 no C3 C4 H4 120.6 no C5 C4 H4 120.6 no C4 C5 H5 119.3 no C6 C5 H5 119.3 no C1 C6 H6 120.4 no C5 C6 H6 120.4 no C9 C10 H10a 109.5 no C9 C10 H10b 109.5 no H10a C10 H10b 109.5 no C9 C10 H10c 109.5 no H10a C10 H10c 109.5 no H10b C10 H10c 109.5 no C12 C13 H13 120.1 no C14 C13 H13 120.1 no C15 C14 H14 119.9 no C13 C14 H14 119.9 no C16 C15 H15 119.8 no C14 C15 H15 119.8 no C15 C16 H16 120.2 no C17 C16 H16 120.2 no C16 C17 H17 119.7 no C12 C17 H17 119.7 no C20 C19 H19 119.7 no C18 C19 H19 119.7 no C21 C20 H20 120.3 no C19 C20 H20 120.3 no C20 C21 H21 119.4 no C22 C21 H21 119.4 no C21 C22 H22 119.5 no C23 C22 H22 119.5 no C23 C24 H24a 109.5 no C23 C24 H24b 109.5 no H24a C24 H24b 109.5 no C23 C24 H24c 109.5 no H24a C24 H24c 109.5 no H24b C24 H24c 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 1.245(2) yes N1 C7 1.376(2) yes N1 N2 1.402(2) yes N1 C1 1.418(2) yes N2 C9 1.300(2) yes N3 C11 1.329(2) yes N3 C18 1.427(2) yes C1 C6 1.377(2) yes C1 C2 1.380(2) yes C2 C3 1.381(2) yes C3 C4 1.357(3) yes C4 C5 1.366(3) yes C5 C6 1.382(3) yes C7 C8 1.441(2) yes C8 C9 1.430(2) yes C8 C11 1.390(2) yes C9 C10 1.497(2) yes C11 C12 1.488(2) yes C12 C13 1.375(2) no C12 C17 1.379(2) no C13 C14 1.381(2) no C14 C15 1.366(3) no C15 C16 1.365(3) no C16 C17 1.375(2) no C18 C19 1.377(2) no C18 C23 1.373(2) no C19 C20 1.366(3) no C20 C21 1.343(4) no C21 C22 1.362(4) no C22 C23 1.410(3) no C23 C24 1.498(3) no N3 H3n 0.870(10) no C2 H2 0.93 no C3 H3 0.93 no C4 H4 0.93 no C5 H5 0.93 no C6 H6 0.93 no C10 H10a 0.96 no C10 H10b 0.96 no C10 H10c 0.96 no C13 H13 0.93 no C14 H14 0.93 no C15 H15 0.93 no C16 H16 0.93 no C17 H17 0.93 no C19 H19 0.93 no C20 H20 0.93 no C21 H21 0.93 no C22 H22 0.93 no C24 H24a 0.96 no C24 H24b 0.96 no C24 H24c 0.96 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 N3 H3n O1 0.870(10) 1.940(10) 2.695(2) 144(2) 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 C7 N1 N2 C9 -1.9(2) no C1 N1 N2 C9 -179.70(10) no C7 N1 C1 C6 12.4(3) no N2 N1 C1 C6 -170.2(2) no C7 N1 C1 C2 -166.9(2) no N2 N1 C1 C2 10.5(2) no C6 C1 C2 C3 -0.8(3) no N1 C1 C2 C3 178.4(2) no C1 C2 C3 C4 0.0(3) no C2 C3 C4 C5 0.1(3) no C3 C4 C5 C6 0.6(3) no C2 C1 C6 C5 1.5(3) no N1 C1 C6 C5 -177.8(2) no C4 C5 C6 C1 -1.4(3) no N2 N1 C7 O1 -177.60(10) no C1 N1 C7 O1 -0.2(3) no N2 N1 C7 C8 2.6(2) no C1 N1 C7 C8 -179.90(10) no O1 C7 C8 C11 -2.6(2) no N1 C7 C8 C11 177.10(10) no O1 C7 C8 C9 178.0(2) no N1 C7 C8 C9 -2.3(2) no N1 N2 C9 C8 0.3(2) no N1 N2 C9 C10 -179.8(2) no C11 C8 C9 N2 -178.1(2) no C7 C8 C9 N2 1.3(2) no C11 C8 C9 C10 2.0(3) no C7 C8 C9 C10 -178.6(2) no C18 N3 C11 C8 -175.1(2) no C18 N3 C11 C12 5.2(2) no C9 C8 C11 N3 -177.3(2) no C7 C8 C11 N3 3.5(2) no C9 C8 C11 C12 2.5(2) no C7 C8 C11 C12 -176.80(10) no N3 C11 C12 C13 84.0(2) no C8 C11 C12 C13 -95.7(2) no N3 C11 C12 C17 -98.6(2) no C8 C11 C12 C17 81.7(2) no C17 C12 C13 C14 -0.7(3) no C11 C12 C13 C14 176.6(2) no C12 C13 C14 C15 1.4(3) no C13 C14 C15 C16 -0.5(3) no C14 C15 C16 C17 -0.9(3) no C15 C16 C17 C12 1.6(3) no C13 C12 C17 C16 -0.7(3) no C11 C12 C17 C16 -178.1(2) no C11 N3 C18 C23 -125.3(2) no C11 N3 C18 C19 58.6(2) no C23 C18 C19 C20 1.1(3) no N3 C18 C19 C20 177.1(2) no C18 C19 C20 C21 -0.7(3) no C19 C20 C21 C22 -0.1(4) no C20 C21 C22 C23 0.7(4) no C19 C18 C23 C22 -0.5(3) no N3 C18 C23 C22 -176.6(2) no C19 C18 C23 C24 178.7(2) no N3 C18 C23 C24 2.7(3) no C21 C22 C23 C18 -0.4(3) no C21 C22 C23 C24 -179.6(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21174470 2 PubChem 136744098