#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206996.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_2206996 loop_ _publ_author_name 'Jing, Zuo-Liang' 'Yu, Ming' 'Chen, Xin' 'Deng, Qi-Liang' _publ_section_title 4-[(2,4-Dichlorobenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3359 _journal_page_last o3360 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H15 Cl2 N3 O' _chemical_formula_moiety 'C18 H15 Cl2 N3 O' _chemical_formula_sum 'C18 H15 Cl2 N3 O' _chemical_formula_weight 360.23 _chemical_name_systematic ; ? ; _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 99.6930(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.4236(7) _cell_length_b 7.3711(5) _cell_length_c 24.5011(18) _cell_measurement_reflns_used 3316 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 25.30 _cell_measurement_theta_min 2.89 _cell_volume 1677.6(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 8814 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.21 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_T_max 0.909 _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1999)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.192 _refine_diff_density_min -0.291 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2935 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0444P)^2^+0.3505P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.0942 _reflns_number_gt 2235 _reflns_number_total 2935 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jh6017.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P2(1)/n _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_database_code 2206996 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 Cl1 0.44691(6) -0.05518(7) 1.06469(2) 0.06103(19) Uani d . 1 Cl Cl2 0.81732(6) 0.27063(10) 1.22497(2) 0.0750(2) Uani d . 1 Cl C11 0.0882(2) 0.8016(3) 0.98549(9) 0.0506(5) Uani d . 1 C H11A 0.1237 0.8969 0.9648 0.076 Uiso calc R 1 H H11B 0.1485 0.7912 1.0211 0.076 Uiso calc R 1 H H11C -0.0085 0.8290 0.9903 0.076 Uiso calc R 1 H N1 0.03425(16) 0.4330(2) 0.88548(6) 0.0409(4) Uani d . 1 N N2 -0.00620(16) 0.5959(2) 0.90848(6) 0.0401(4) Uani d . 1 N N3 0.28447(15) 0.4723(2) 1.01440(6) 0.0382(4) Uani d . 1 N C1 0.46740(19) 0.3109(2) 1.07464(7) 0.0373(4) Uani d . 1 C C2 0.5203(2) 0.1435(3) 1.09530(8) 0.0423(5) Uani d . 1 C C3 0.6284(2) 0.1288(3) 1.14104(8) 0.0506(5) Uani d . 1 C H3 0.6636 0.0160 1.1538 0.061 Uiso calc R 1 H C4 0.6822(2) 0.2856(3) 1.16710(8) 0.0483(5) Uani d . 1 C C5 0.6326(2) 0.4533(3) 1.14840(8) 0.0476(5) Uani d . 1 C H5 0.6698 0.5579 1.1667 0.057 Uiso calc R 1 H C6 0.5271(2) 0.4646(3) 1.10224(8) 0.0432(5) Uani d . 1 C H6 0.4950 0.5783 1.0892 0.052 Uiso calc R 1 H C7 0.35588(19) 0.3251(2) 1.02526(7) 0.0391(4) Uani d . 1 C H7 0.3368 0.2262 1.0016 0.047 Uiso calc R 1 H C8 0.18082(18) 0.4828(2) 0.96690(7) 0.0354(4) Uani d . 1 C C9 0.08972(19) 0.6280(2) 0.95513(7) 0.0370(4) Uani d . 1 C C10 0.14472(19) 0.3513(2) 0.92327(7) 0.0385(4) Uani d . 1 C O1 0.19010(15) 0.19821(18) 0.91639(6) 0.0526(4) Uani d . 1 O C12 -0.0797(2) 0.7352(3) 0.87217(9) 0.0567(6) Uani d . 1 C H12A -0.1233 0.8212 0.8937 0.085 Uiso calc R 1 H H12B -0.1528 0.6801 0.8453 0.085 Uiso calc R 1 H H12C -0.0115 0.7963 0.8536 0.085 Uiso calc R 1 H C13 -0.0674(2) 0.3308(2) 0.84841(7) 0.0401(4) Uani d . 1 C C14 -0.0177(2) 0.2350(3) 0.80691(8) 0.0522(5) Uani d . 1 C H14 0.0783 0.2434 0.8027 0.063 Uiso calc R 1 H C15 -0.1117(3) 0.1268(3) 0.77185(9) 0.0634(6) Uani d . 1 C H15 -0.0788 0.0615 0.7440 0.076 Uiso calc R 1 H C16 -0.2532(3) 0.1153(3) 0.77790(9) 0.0634(6) Uani d . 1 C H16 -0.3160 0.0411 0.7544 0.076 Uiso calc R 1 H C17 -0.3025(2) 0.2133(3) 0.81859(9) 0.0609(6) Uani d . 1 C H17 -0.3992 0.2074 0.8219 0.073 Uiso calc R 1 H C18 -0.2097(2) 0.3205(3) 0.85452(8) 0.0502(5) Uani d . 1 C H18 -0.2429 0.3849 0.8825 0.060 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 Cl1 0.0749(4) 0.0349(3) 0.0688(4) 0.0005(2) -0.0010(3) 0.0033(2) Cl2 0.0586(4) 0.1057(5) 0.0524(3) 0.0053(3) -0.0145(3) 0.0102(3) C11 0.0579(13) 0.0362(11) 0.0545(12) 0.0072(9) 0.0000(10) -0.0071(9) N1 0.0411(9) 0.0369(8) 0.0417(9) 0.0088(7) -0.0021(7) -0.0070(7) N2 0.0436(9) 0.0316(8) 0.0421(9) 0.0093(7) -0.0016(7) -0.0014(7) N3 0.0379(8) 0.0362(9) 0.0382(8) 0.0043(7) 0.0002(7) -0.0002(7) C1 0.0360(10) 0.0365(10) 0.0390(10) 0.0048(8) 0.0053(8) 0.0031(8) C2 0.0441(11) 0.0368(11) 0.0453(11) 0.0026(8) 0.0057(9) 0.0035(8) C3 0.0493(12) 0.0500(12) 0.0504(12) 0.0101(10) 0.0020(10) 0.0131(10) C4 0.0374(11) 0.0660(14) 0.0395(11) 0.0035(10) 0.0009(9) 0.0073(10) C5 0.0431(11) 0.0498(12) 0.0481(12) -0.0034(9) 0.0020(9) -0.0044(10) C6 0.0432(11) 0.0365(11) 0.0483(11) 0.0039(8) 0.0029(9) 0.0014(9) C7 0.0399(10) 0.0358(10) 0.0396(10) 0.0026(8) 0.0005(8) -0.0016(8) C8 0.0366(10) 0.0320(9) 0.0363(10) 0.0034(8) 0.0029(8) -0.0003(7) C9 0.0394(10) 0.0306(9) 0.0396(10) 0.0012(8) 0.0028(8) 0.0003(8) C10 0.0371(10) 0.0357(10) 0.0407(10) 0.0055(8) 0.0014(8) 0.0004(8) O1 0.0561(9) 0.0393(8) 0.0568(9) 0.0165(7) -0.0064(7) -0.0112(6) C12 0.0669(14) 0.0482(13) 0.0505(13) 0.0213(11) -0.0036(11) 0.0082(10) C13 0.0437(11) 0.0380(10) 0.0350(10) 0.0044(8) -0.0039(8) -0.0001(8) C14 0.0519(12) 0.0560(13) 0.0465(12) 0.0063(10) 0.0020(10) -0.0098(10) C15 0.0748(17) 0.0605(15) 0.0508(13) 0.0085(12) -0.0014(12) -0.0173(11) C16 0.0762(17) 0.0577(14) 0.0479(13) -0.0105(12) -0.0138(12) -0.0039(11) C17 0.0474(12) 0.0814(17) 0.0491(13) -0.0108(12) -0.0056(10) 0.0055(12) C18 0.0468(12) 0.0630(14) 0.0387(11) 0.0011(10) 0.0015(9) -0.0008(10) 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 C9 C11 H11A 109.5 ? C9 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C9 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? N2 N1 C10 108.80(14) yes N2 N1 C13 120.67(14) yes C10 N1 C13 122.58(15) yes C9 N2 N1 107.46(13) yes C9 N2 C12 125.05(16) yes N1 N2 C12 119.41(15) yes C7 N3 C8 119.45(15) yes C6 C1 C2 117.03(17) ? C6 C1 C7 121.27(16) ? C2 C1 C7 121.69(17) ? C3 C2 C1 122.12(18) ? C3 C2 Cl1 117.99(15) ? C1 C2 Cl1 119.87(15) ? C4 C3 C2 118.27(19) ? C4 C3 H3 120.9 ? C2 C3 H3 120.9 ? C5 C4 C3 121.57(18) ? C5 C4 Cl2 119.31(17) ? C3 C4 Cl2 119.12(16) ? C4 C5 C6 119.14(19) ? C4 C5 H5 120.4 ? C6 C5 H5 120.4 ? C5 C6 C1 121.87(18) ? C5 C6 H6 119.1 ? C1 C6 H6 119.1 ? N3 C7 C1 120.66(17) ? N3 C7 H7 119.7 ? C1 C7 H7 119.7 ? C9 C8 N3 123.10(16) ? C9 C8 C10 107.91(15) ? N3 C8 C10 128.97(16) ? N2 C9 C8 110.28(15) ? N2 C9 C11 120.91(16) ? C8 C9 C11 128.81(17) ? O1 C10 N1 122.62(16) ? O1 C10 C8 132.50(17) ? N1 C10 C8 104.87(15) ? N2 C12 H12A 109.5 ? N2 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? N2 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? C18 C13 C14 120.56(18) ? C18 C13 N1 121.62(16) ? C14 C13 N1 117.77(17) ? C15 C14 C13 119.5(2) ? C15 C14 H14 120.3 ? C13 C14 H14 120.3 ? C16 C15 C14 120.2(2) ? C16 C15 H15 119.9 ? C14 C15 H15 119.9 ? C15 C16 C17 120.0(2) ? C15 C16 H16 120.0 ? C17 C16 H16 120.0 ? C16 C17 C18 120.6(2) ? C16 C17 H17 119.7 ? C18 C17 H17 119.7 ? C13 C18 C17 119.10(19) ? C13 C18 H18 120.4 ? C17 C18 H18 120.4 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 1.735(2) yes Cl2 C4 1.742(2) yes C11 C9 1.481(3) ? C11 H11A 0.9600 ? C11 H11B 0.9600 ? C11 H11C 0.9600 ? N1 N2 1.406(2) yes N1 C10 1.407(2) ? N1 C13 1.420(2) ? N2 C9 1.353(2) ? N2 C12 1.456(2) ? N3 C7 1.281(2) yes N3 C8 1.390(2) yes C1 C6 1.389(3) ? C1 C2 1.394(3) ? C1 C7 1.467(2) ? C2 C3 1.386(3) ? C3 C4 1.375(3) ? C3 H3 0.9300 ? C4 C5 1.373(3) ? C5 C6 1.377(3) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 H7 0.9300 ? C8 C9 1.372(2) ? C8 C10 1.440(2) ? C10 O1 1.229(2) ? C12 H12A 0.9600 ? C12 H12B 0.9600 ? C12 H12C 0.9600 ? C13 C18 1.377(3) ? C13 C14 1.383(3) ? C14 C15 1.379(3) ? C14 H14 0.9300 ? C15 C16 1.369(3) ? C15 H15 0.9300 ? C16 C17 1.374(3) ? C16 H16 0.9300 ? C17 C18 1.380(3) ? C17 H17 0.9300 ? C18 H18 0.9300 ? 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 C7 H7 O1 . 0.93 2.31 3.005(2) 131.0 yes C6 H6 Cl1 1_565 0.93 2.79 3.703(2) 168.4 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 C10 N1 N2 C9 8.62(19) C13 N1 N2 C9 158.31(16) C10 N1 N2 C12 158.89(17) C13 N1 N2 C12 -51.4(2) C6 C1 C2 C3 -0.4(3) C7 C1 C2 C3 178.23(17) C6 C1 C2 Cl1 177.69(14) C7 C1 C2 Cl1 -3.6(2) C1 C2 C3 C4 1.2(3) Cl1 C2 C3 C4 -176.92(15) C2 C3 C4 C5 -0.8(3) C2 C3 C4 Cl2 179.59(14) C3 C4 C5 C6 -0.4(3) Cl2 C4 C5 C6 179.18(15) C4 C5 C6 C1 1.3(3) C2 C1 C6 C5 -0.8(3) C7 C1 C6 C5 -179.52(17) C8 N3 C7 C1 179.09(15) C6 C1 C7 N3 -18.1(3) C2 C1 C7 N3 163.25(17) C7 N3 C8 C9 173.14(17) C7 N3 C8 C10 -4.8(3) N1 N2 C9 C8 -7.0(2) C12 N2 C9 C8 -155.10(18) N1 N2 C9 C11 172.20(17) C12 N2 C9 C11 24.1(3) N3 C8 C9 N2 -175.64(16) C10 C8 C9 N2 2.7(2) N3 C8 C9 C11 5.3(3) C10 C8 C9 C11 -176.38(19) N2 N1 C10 O1 172.16(17) C13 N1 C10 O1 23.2(3) N2 N1 C10 C8 -6.80(19) C13 N1 C10 C8 -155.80(16) C9 C8 C10 O1 -176.2(2) N3 C8 C10 O1 2.0(3) C9 C8 C10 N1 2.63(19) N3 C8 C10 N1 -179.17(17) N2 N1 C13 C18 -35.2(3) C10 N1 C13 C18 110.3(2) N2 N1 C13 C14 147.44(18) C10 N1 C13 C14 -67.1(2) C18 C13 C14 C15 -0.7(3) N1 C13 C14 C15 176.71(19) C13 C14 C15 C16 0.4(4) C14 C15 C16 C17 0.7(4) C15 C16 C17 C18 -1.6(4) C14 C13 C18 C17 -0.1(3) N1 C13 C18 C17 -177.43(19) C16 C17 C18 C13 1.2(3) _journal_paper_doi 10.1107/S1600536805029624