#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203329.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
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_melting_point        ?
_chemical_name_common          ?
_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_detector_area_resol_mean ?
_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_meas    ?
_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_disorder_assembly
_atom_site_disorder_group
_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_site_symmetry_1
_geom_angle_site_symmetry_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_site_symmetry_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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
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) ?