#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205081.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_2205081 loop_ _publ_author_name 'Zhang, Xin-Li' 'Li, Zong-Xiao' _publ_section_title ;4-[(4-Hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one methanol solvate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o266 _journal_page_last o268 _journal_paper_doi 10.1107/S1600536804034324 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H17 N3 O2, C H4 O' _chemical_formula_moiety 'C18 H17 N3 O2, C H4 O' _chemical_formula_sum 'C19 H21 N3 O3' _chemical_formula_weight 339.39 _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 108.292(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.680(9) _cell_length_b 6.916(5) _cell_length_c 19.968(14) _cell_measurement_reflns_used 1346 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.985 _cell_measurement_theta_min 3.111 _cell_volume 1794(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _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 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 '\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 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 8910 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.161 _refine_diff_density_min -0.169 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 3162 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0484 _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^)+(0.0571P)^2^+0.0741P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.1418 _reflns_number_gt 1498 _reflns_number_total 3162 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hg6125.cif _cod_data_source_block I _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_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2205081 _cod_database_fobs_code 2205081 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 O1 0.83700(14) -0.1637(3) 0.11322(11) 0.0592(6) Uani d . 1 O O2 0.19408(15) -0.2549(3) 0.02847(13) 0.0733(7) Uani d . 1 O H2 0.1825 -0.3646 0.0123 0.110 Uiso calc R 1 H O3 0.1424(2) 0.3787(4) -0.00736(15) 0.0997(9) Uani d . 1 O H3A 0.1466 0.3103 -0.0399 0.149 Uiso calc R 1 H N1 0.92859(17) 0.1059(3) 0.16723(12) 0.0478(6) Uani d . 1 N N2 0.90488(17) 0.2765(3) 0.19727(12) 0.0493(6) Uani d . 1 N N3 0.65076(17) 0.0904(3) 0.12427(12) 0.0498(6) Uani d . 1 N C1 0.2967(2) -0.2153(5) 0.04429(16) 0.0541(8) Uani d . 1 C C2 0.3654(2) -0.3429(4) 0.03252(15) 0.0564(8) Uani d . 1 C H2A 0.3434 -0.4637 0.0131 0.068 Uiso calc R 1 H C3 0.4675(2) -0.2923(5) 0.04946(16) 0.0577(9) Uani d . 1 C H3 0.5136 -0.3804 0.0410 0.069 Uiso calc R 1 H C4 0.5040(2) -0.1152(4) 0.07867(14) 0.0472(7) Uani d . 1 C C5 0.4337(2) 0.0102(5) 0.09091(16) 0.0624(9) Uani d . 1 C H5 0.4556 0.1304 0.1109 0.075 Uiso calc R 1 H C6 0.3312(2) -0.0390(5) 0.07409(17) 0.0686(10) Uani d . 1 C H6 0.2849 0.0479 0.0830 0.082 Uiso calc R 1 H C7 0.6124(2) -0.0666(4) 0.09428(14) 0.0511(8) Uani d . 1 C H7 0.6553 -0.1541 0.0818 0.061 Uiso calc R 1 H C8 0.7561(2) 0.1277(4) 0.14170(14) 0.0432(7) Uani d . 1 C C9 0.8375(2) 0.0040(4) 0.13597(14) 0.0461(7) Uani d . 1 C C10 0.8006(2) 0.2903(4) 0.17612(14) 0.0445(7) Uani d . 1 C C11 0.7479(2) 0.4640(4) 0.19167(16) 0.0658(9) Uani d . 1 C H11A 0.7768 0.4970 0.2406 0.099 Uiso calc R 1 H H11B 0.6758 0.4374 0.1813 0.099 Uiso calc R 1 H H11C 0.7569 0.5701 0.1632 0.099 Uiso calc R 1 H C12 0.9752(2) 0.4388(4) 0.20375(18) 0.0706(10) Uani d . 1 C H12A 0.9735 0.4811 0.1576 0.106 Uiso calc R 1 H H12B 1.0438 0.3991 0.2299 0.106 Uiso calc R 1 H H12C 0.9545 0.5432 0.2280 0.106 Uiso calc R 1 H C13 1.0238(2) 0.0107(4) 0.20212(16) 0.0456(7) Uani d . 1 C C14 1.0718(2) -0.0904(4) 0.16144(16) 0.0516(8) Uani d . 1 C H14 1.0443 -0.0897 0.1125 0.062 Uiso calc R 1 H C15 1.1604(2) -0.1916(4) 0.19389(19) 0.0612(9) Uani d . 1 C H15 1.1925 -0.2613 0.1668 0.073 Uiso calc R 1 H C16 1.2020(2) -0.1905(5) 0.2663(2) 0.0656(10) Uani d . 1 C H16 1.2622 -0.2590 0.2879 0.079 Uiso calc R 1 H C17 1.1549(2) -0.0883(5) 0.30680(17) 0.0629(9) Uani d . 1 C H17 1.1836 -0.0866 0.3556 0.075 Uiso calc R 1 H C18 1.0652(2) 0.0115(4) 0.27478(16) 0.0542(8) Uani d . 1 C H18 1.0325 0.0791 0.3020 0.065 Uiso calc R 1 H C19 0.0846(3) 0.2843(6) 0.0288(2) 0.0897(12) Uani d . 1 C H19A 0.0962 0.3440 0.0740 0.135 Uiso calc R 1 H H19B 0.1049 0.1509 0.0351 0.135 Uiso calc R 1 H H19C 0.0129 0.2926 0.0022 0.135 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 0.0514(13) 0.0451(14) 0.0776(16) -0.0030(10) 0.0153(11) -0.0178(11) O2 0.0426(13) 0.0788(18) 0.1008(19) -0.0092(11) 0.0258(12) -0.0183(15) O3 0.126(2) 0.0776(19) 0.121(2) -0.0362(17) 0.075(2) -0.0399(16) N1 0.0415(14) 0.0380(15) 0.0590(16) 0.0001(12) 0.0088(12) -0.0045(12) N2 0.0474(16) 0.0340(15) 0.0613(16) -0.0029(12) 0.0097(12) -0.0056(12) N3 0.0423(15) 0.0530(17) 0.0519(16) -0.0022(13) 0.0116(12) -0.0021(13) C1 0.0393(18) 0.065(2) 0.058(2) -0.0035(17) 0.0161(15) -0.0040(17) C2 0.052(2) 0.056(2) 0.063(2) -0.0091(17) 0.0200(16) -0.0153(17) C3 0.0412(19) 0.062(2) 0.070(2) 0.0013(16) 0.0171(16) -0.0122(18) C4 0.0413(18) 0.052(2) 0.0463(18) 0.0013(15) 0.0111(14) -0.0011(15) C5 0.050(2) 0.053(2) 0.085(2) -0.0052(17) 0.0228(18) -0.0133(18) C6 0.048(2) 0.060(2) 0.099(3) -0.0015(17) 0.0256(18) -0.021(2) C7 0.0447(19) 0.056(2) 0.051(2) 0.0013(16) 0.0117(15) -0.0020(16) C8 0.0404(18) 0.0438(18) 0.0447(18) 0.0018(15) 0.0123(14) 0.0008(14) C9 0.0459(18) 0.043(2) 0.0468(18) -0.0055(16) 0.0108(14) 0.0016(15) C10 0.0470(19) 0.0389(19) 0.0479(19) 0.0030(15) 0.0155(15) 0.0045(14) C11 0.066(2) 0.051(2) 0.079(2) 0.0079(17) 0.0215(18) -0.0045(17) C12 0.059(2) 0.043(2) 0.104(3) -0.0138(16) 0.0176(19) -0.0055(18) C13 0.0373(16) 0.0408(18) 0.056(2) -0.0021(14) 0.0103(15) 0.0015(15) C14 0.0471(19) 0.049(2) 0.058(2) -0.0033(16) 0.0154(16) -0.0018(16) C15 0.054(2) 0.053(2) 0.078(3) 0.0049(17) 0.0221(19) -0.0083(18) C16 0.047(2) 0.056(2) 0.086(3) 0.0042(16) 0.010(2) 0.007(2) C17 0.055(2) 0.067(2) 0.062(2) 0.0063(18) 0.0119(18) 0.0103(19) C18 0.0505(19) 0.054(2) 0.058(2) 0.0019(16) 0.0167(16) -0.0002(16) C19 0.069(3) 0.096(3) 0.108(3) -0.007(2) 0.034(2) 0.000(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 C1 O2 H2 109.5 C19 O3 H3A 109.5 C9 N1 N2 108.7(2) C9 N1 C13 122.3(2) N2 N1 C13 118.3(2) C10 N2 N1 106.7(2) C10 N2 C12 124.9(2) N1 N2 C12 116.7(2) C7 N3 C8 121.1(2) C2 C1 O2 123.0(3) C2 C1 C6 119.2(3) O2 C1 C6 117.8(3) C1 C2 C3 119.7(3) C1 C2 H2A 120.2 C3 C2 H2A 120.2 C2 C3 C4 122.3(3) C2 C3 H3 118.9 C4 C3 H3 118.9 C5 C4 C3 117.1(3) C5 C4 C7 122.7(3) C3 C4 C7 120.2(3) C4 C5 C6 121.1(3) C4 C5 H5 119.5 C6 C5 H5 119.5 C1 C6 C5 120.6(3) C1 C6 H6 119.7 C5 C6 H6 119.7 N3 C7 C4 122.7(3) N3 C7 H7 118.6 C4 C7 H7 118.6 C10 C8 N3 122.9(3) C10 C8 C9 107.3(2) N3 C8 C9 129.4(3) O1 C9 N1 122.3(3) O1 C9 C8 132.0(3) N1 C9 C8 105.6(2) N2 C10 C8 111.1(2) N2 C10 C11 121.6(3) C8 C10 C11 127.3(3) C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 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 120.3(3) C18 C13 N1 121.3(3) C14 C13 N1 118.3(3) C15 C14 C13 119.5(3) C15 C14 H14 120.3 C13 C14 H14 120.3 C14 C15 C16 120.4(3) C14 C15 H15 119.8 C16 C15 H15 119.8 C15 C16 C17 120.3(3) C15 C16 H16 119.9 C17 C16 H16 119.9 C16 C17 C18 119.8(3) C16 C17 H17 120.1 C18 C17 H17 120.1 C17 C18 C13 119.8(3) C17 C18 H18 120.1 C13 C18 H18 120.1 O3 C19 H19A 109.5 O3 C19 H19B 109.5 H19A C19 H19B 109.5 O3 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.245(3) O2 C1 1.366(3) O2 H2 0.8200 O3 C19 1.389(4) O3 H3A 0.8200 N1 C9 1.397(3) N1 N2 1.407(3) N1 C13 1.430(3) N2 C10 1.358(3) N2 C12 1.457(3) N3 C7 1.271(3) N3 C8 1.396(3) C1 C2 1.363(4) C1 C6 1.373(4) C2 C3 1.376(4) C2 H2A 0.9300 C3 C4 1.381(4) C3 H3 0.9300 C4 C5 1.372(4) C4 C7 1.455(4) C5 C6 1.379(4) C5 H5 0.9300 C6 H6 0.9300 C7 H7 0.9300 C8 C10 1.358(4) C8 C9 1.436(4) C10 C11 1.484(4) C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C13 C18 1.382(4) C13 C14 1.384(4) C14 C15 1.374(4) C14 H14 0.9300 C15 C16 1.377(4) C15 H15 0.9300 C16 C17 1.378(4) C16 H16 0.9300 C17 C18 1.378(4) C17 H17 0.9300 C18 H18 0.9300 C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 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 O2 H2 O3 1_545 0.82 1.86 2.668(4) 166.4 O3 H3A O1 3_655 0.82 1.85 2.671(3) 176.7 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654777