#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203329.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_2203329 loop_ _publ_author_name 'Zhu, Hong-Jun' 'Ma, Ji' 'Wei, Chang-Mei' 'Wang, Jin-Tang' _publ_section_title ; (+-)-5-(3,4-Dimethoxyphenyl)-1-phenylpyrazolidin-3-one ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o411 _journal_page_last o413 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H18 N2 O3' _chemical_formula_moiety 'C17 H18 N2 O3' _chemical_formula_sum 'C17 H18 N2 O3' _chemical_formula_weight 298.33 _chemical_name_systematic ; 5-(3,4-dimethoxyphenyl)-1-phenylpyrazolidin-3-one ; _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 66.49(3) _cell_angle_beta 67.67(3) _cell_angle_gamma 62.05(3) _cell_formula_units_Z 2 _cell_length_a 9.011(2) _cell_length_b 9.403(2) _cell_length_c 11.621(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 10 _cell_volume 774.6(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms, 1995)' _computing_molecular_graphics 'please provide' _computing_publication_material SHELXS97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Nonius CAD-4/PC' _diffrn_measurement_method \w/2\q _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 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2902 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.97 _diffrn_standards_decay_% 0.9 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.268 _refine_diff_density_min -0.298 _refine_ls_extinction_coef 0.058(17) _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 1.178 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 2715 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.178 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0651 _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^)+(0.16P)^2^+0.4P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2449 _refine_ls_wR_factor_ref 0.2753 _reflns_number_gt 2090 _reflns_number_total 2715 _reflns_threshold_expression I>2\s(I) 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 -0.3102(3) 1.3251(3) -0.0519(3) 0.0620(8) Uani d . 1 O O2 0.1139(4) 0.7080(3) 0.4494(2) 0.0620(8) Uani d . 1 O O3 -0.1625(4) 0.7390(3) 0.6302(3) 0.0704(9) Uani d . 1 O N1 -0.3602(4) 1.4563(4) 0.0948(3) 0.0513(8) Uani d . 1 N N2 -0.2882(3) 1.4402(3) 0.1907(3) 0.0438(7) Uani d . 1 N C1 -0.2652(4) 1.3452(4) 0.0268(3) 0.0466(8) Uani d . 1 C C2 -0.0951(4) 1.2487(5) 0.0636(3) 0.0514(9) Uani d . 1 C H2A -0.0057 1.2859 -0.0027 0.062 Uiso calc R 1 H H2B -0.0602 1.1299 0.0765 0.062 Uiso calc R 1 H C3 -0.1280(4) 1.2858(4) 0.1900(3) 0.0424(8) Uani d . 1 C H3A -0.0320 1.3112 0.1859 0.051 Uiso calc R 1 H C4 -0.2773(4) 1.5864(4) 0.1881(3) 0.0413(8) Uani d . 1 C C5 -0.3492(4) 1.7418(4) 0.1071(3) 0.0499(9) Uani d . 1 C H5A -0.3996 1.7524 0.0461 0.060 Uiso calc R 1 H C6 -0.3452(5) 1.8818(5) 0.1183(5) 0.0671(11) Uani d . 1 C H6A -0.3939 1.9864 0.0645 0.080 Uiso calc R 1 H C7 -0.2706(6) 1.8684(6) 0.2073(5) 0.0725(13) Uani d . 1 C H7A -0.2690 1.9629 0.2142 0.087 Uiso calc R 1 H C8 -0.1988(6) 1.7139(6) 0.2859(4) 0.0708(12) Uani d . 1 C H8A -0.1468 1.7037 0.3458 0.085 Uiso calc R 1 H C9 -0.2020(5) 1.5765(5) 0.2778(4) 0.0568(10) Uani d . 1 C H9A -0.1534 1.4730 0.3330 0.068 Uiso calc R 1 H C10 -0.1475(4) 1.1442(4) 0.3094(3) 0.0375(7) Uani d . 1 C C11 -0.2961(4) 1.1583(4) 0.4069(3) 0.0491(9) Uani d . 1 C H11A -0.3906 1.2592 0.4003 0.059 Uiso calc R 1 H C12 -0.3073(5) 1.0244(5) 0.5151(3) 0.0538(9) Uani d . 1 C H12A -0.4096 1.0355 0.5792 0.065 Uiso calc R 1 H C13 -0.1684(4) 0.8765(4) 0.5275(3) 0.0478(8) Uani d . 1 C C14 -0.0149(4) 0.8597(4) 0.4288(3) 0.0438(8) Uani d . 1 C C15 -0.0074(4) 0.9924(4) 0.3217(3) 0.0429(8) Uani d . 1 C H15A 0.0934 0.9806 0.2561 0.052 Uiso calc R 1 H C16 -0.3095(7) 0.7454(7) 0.7307(5) 0.1002(19) Uani d . 1 C H16A -0.2872 0.6405 0.7960 0.150 Uiso calc R 1 H H16B -0.4035 0.7668 0.6983 0.150 Uiso calc R 1 H H16C -0.3394 0.8334 0.7672 0.150 Uiso calc R 1 H C17 0.2727(6) 0.6835(6) 0.3544(4) 0.0834(15) Uani d . 1 C H17A 0.3525 0.5711 0.3802 0.125 Uiso calc R 1 H H17B 0.3202 0.7609 0.3454 0.125 Uiso calc R 1 H H17C 0.2528 0.7018 0.2732 0.125 Uiso calc R 1 H H1 -0.484(7) 1.509(6) 0.102(5) 0.089(15) Uiso d . 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 0.0599(16) 0.0665(17) 0.0646(16) -0.0085(13) -0.0313(13) -0.0254(13) O2 0.0620(16) 0.0437(14) 0.0506(14) 0.0038(11) -0.0186(12) -0.0083(11) O3 0.0672(18) 0.0606(17) 0.0556(16) -0.0226(14) -0.0165(13) 0.0108(13) N1 0.0493(17) 0.0485(16) 0.0646(19) -0.0089(13) -0.0315(15) -0.0178(14) N2 0.0463(15) 0.0394(15) 0.0485(15) -0.0143(12) -0.0244(12) -0.0040(11) C1 0.0471(18) 0.0451(18) 0.0437(17) -0.0139(14) -0.0161(14) -0.0072(14) C2 0.0431(18) 0.059(2) 0.0370(17) -0.0115(15) -0.0109(14) -0.0071(15) C3 0.0374(16) 0.0394(17) 0.0484(18) -0.0147(13) -0.0157(13) -0.0044(13) C4 0.0375(16) 0.0435(17) 0.0407(16) -0.0127(13) -0.0106(13) -0.0111(13) C5 0.0466(18) 0.0431(18) 0.055(2) -0.0099(14) -0.0216(15) -0.0085(15) C6 0.058(2) 0.040(2) 0.093(3) -0.0095(16) -0.020(2) -0.0166(19) C7 0.063(2) 0.067(3) 0.104(3) -0.026(2) -0.010(2) -0.048(3) C8 0.075(3) 0.084(3) 0.075(3) -0.031(2) -0.022(2) -0.038(2) C9 0.067(2) 0.063(2) 0.050(2) -0.0261(19) -0.0255(17) -0.0116(17) C10 0.0410(16) 0.0377(16) 0.0357(15) -0.0108(13) -0.0164(12) -0.0097(12) C11 0.0445(18) 0.0435(18) 0.0480(19) -0.0061(14) -0.0168(15) -0.0089(15) C12 0.0437(18) 0.058(2) 0.0449(19) -0.0142(16) -0.0070(14) -0.0093(16) C13 0.0512(19) 0.0461(18) 0.0425(18) -0.0176(15) -0.0173(15) -0.0035(14) C14 0.0492(18) 0.0375(16) 0.0412(17) -0.0065(14) -0.0190(14) -0.0113(13) C15 0.0441(17) 0.0458(18) 0.0358(16) -0.0113(14) -0.0134(13) -0.0110(13) C16 0.081(3) 0.098(4) 0.073(3) -0.039(3) -0.012(3) 0.023(3) C17 0.071(3) 0.069(3) 0.062(3) 0.014(2) -0.015(2) -0.022(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 C14 O2 C17 117.7(3) yes C13 O3 C16 118.4(3) yes C1 N1 N2 115.0(3) yes C1 N1 H1 119(3) ? N2 N1 H1 121(3) ? C4 N2 N1 116.1(2) ? C4 N2 C3 118.2(2) ? N1 N2 C3 105.6(2) yes O1 C1 N1 125.9(3) yes O1 C1 C2 126.6(3) ? N1 C1 C2 107.5(3) yes C1 C2 C3 104.3(3) yes C1 C2 H2A 110.9 ? C3 C2 H2A 110.9 ? C1 C2 H2B 110.9 ? C3 C2 H2B 110.9 ? H2A C2 H2B 108.9 ? N2 C3 C10 112.1(3) ? N2 C3 C2 104.0(2) ? C10 C3 C2 113.9(3) ? N2 C3 H3A 108.9 ? C10 C3 H3A 108.9 ? C2 C3 H3A 108.9 ? C5 C4 C9 118.4(3) ? C5 C4 N2 122.8(3) ? C9 C4 N2 118.5(3) ? C4 C5 C6 119.1(3) ? C4 C5 H5A 120.5 ? C6 C5 H5A 120.5 ? C7 C6 C5 121.2(4) ? C7 C6 H6A 119.4 ? C5 C6 H6A 119.4 ? C8 C7 C6 119.0(4) ? C8 C7 H7A 120.5 ? C6 C7 H7A 120.5 ? C9 C8 C7 121.1(4) ? C9 C8 H8A 119.5 ? C7 C8 H8A 119.5 ? C8 C9 C4 121.2(4) ? C8 C9 H9A 119.4 ? C4 C9 H9A 119.4 ? C11 C10 C15 118.4(3) ? C11 C10 C3 123.3(3) ? C15 C10 C3 118.3(3) ? C10 C11 C12 121.2(3) ? C10 C11 H11A 119.4 ? C12 C11 H11A 119.4 ? C13 C12 C11 120.1(3) ? C13 C12 H12A 119.9 ? C11 C12 H12A 119.9 ? O3 C13 C12 125.4(3) ? O3 C13 C14 115.1(3) ? C12 C13 C14 119.5(3) ? O2 C14 C15 125.6(3) ? O2 C14 C13 114.9(3) ? C15 C14 C13 119.4(3) ? C14 C15 C10 121.3(3) ? C14 C15 H15A 119.3 ? C10 C15 H15A 119.3 ? O3 C16 H16A 109.5 ? O3 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? O3 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? O2 C17 H17A 109.5 ? O2 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? O2 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.236(4) yes O2 C14 1.351(4) yes O2 C17 1.419(5) yes O3 C13 1.361(4) yes O3 C16 1.388(6) yes N1 C1 1.324(5) yes N1 N2 1.417(4) yes N1 H1 0.97(5) ? N2 C4 1.411(4) yes N2 C3 1.492(4) yes C1 C2 1.496(5) yes C2 C3 1.533(5) yes C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C10 1.513(4) yes C3 H3A 0.9800 ? C4 C5 1.385(5) ? C4 C9 1.398(5) ? C5 C6 1.392(5) ? C5 H5A 0.9300 ? C6 C7 1.371(6) ? C6 H6A 0.9300 ? C7 C8 1.368(7) ? C7 H7A 0.9300 ? C8 C9 1.346(6) ? C8 H8A 0.9300 ? C9 H9A 0.9300 ? C10 C11 1.376(5) ? C10 C15 1.391(4) ? C11 C12 1.392(5) ? C11 H11A 0.9300 ? C12 C13 1.366(5) ? C12 H12A 0.9300 ? C13 C14 1.410(5) ? C14 C15 1.373(5) ? C15 H15A 0.9300 ? C16 H16A 0.9600 ? C16 H16B 0.9600 ? C16 H16C 0.9600 ? C17 H17A 0.9600 ? C17 H17B 0.9600 ? C17 H17C 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 _geom_hbond_publ_flag N1 H1 O1 2_485 0.97(5) 1.90(6) 2.807(5) 155(5) yes C9 H9A O2 2_576 0.93 2.47 3.315(5) 151 yes C17 H17C O1 2_575 0.96 2.52 3.432(5) 159 yes C2 H2A Cg1 2_585 0.97 2.66 3.576(4) 157 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 C1 N1 N2 C4 128.0(3) C1 N1 N2 C3 -5.0(4) N2 N1 C1 O1 172.1(3) N2 N1 C1 C2 -7.5(4) O1 C1 C2 C3 -163.3(3) N1 C1 C2 C3 16.4(4) C4 N2 C3 C10 119.3(3) N1 N2 C3 C10 -108.8(3) C4 N2 C3 C2 -117.1(3) N1 N2 C3 C2 14.7(3) C1 C2 C3 N2 -18.7(3) C1 C2 C3 C10 103.6(3) N1 N2 C4 C5 7.1(4) C3 N2 C4 C5 134.0(3) N1 N2 C4 C9 -177.9(3) C3 N2 C4 C9 -50.9(4) C9 C4 C5 C6 -0.4(5) N2 C4 C5 C6 174.6(3) C4 C5 C6 C7 0.3(6) C5 C6 C7 C8 0.2(6) C6 C7 C8 C9 -0.7(7) C7 C8 C9 C4 0.7(7) C5 C4 C9 C8 -0.1(6) N2 C4 C9 C8 -175.4(3) N2 C3 C10 C11 -0.4(4) C2 C3 C10 C11 -118.2(3) N2 C3 C10 C15 -179.8(2) C2 C3 C10 C15 62.5(4) C15 C10 C11 C12 -0.4(5) C3 C10 C11 C12 -179.7(3) C10 C11 C12 C13 1.3(5) C16 O3 C13 C12 1.4(6) C16 O3 C13 C14 -179.4(4) C11 C12 C13 O3 178.1(3) C11 C12 C13 C14 -1.1(5) C17 O2 C14 C15 1.7(5) C17 O2 C14 C13 -179.3(4) O3 C13 C14 O2 1.7(4) C12 C13 C14 O2 -179.1(3) O3 C13 C14 C15 -179.3(3) C12 C13 C14 C15 0.0(5) O2 C14 C15 C10 179.9(3) C13 C14 C15 C10 1.0(5) C11 C10 C15 C14 -0.8(5) C3 C10 C15 C14 178.6(3) _cod_database_code 2203329