#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/17/2211736.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_2211736
loop_
_publ_author_name
'Li, Zong-Xiao'
'Zhang, Xin-Li'
_publ_section_title
4-[(2-Methoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazolidin-3(2H)-one
_journal_coeditor_code           BI2117
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o357
_journal_page_last               o358
_journal_paper_doi               10.1107/S1600536806054171
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H19 N3 O2'
_chemical_formula_moiety         'C19 H19 N3 O2'
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_weight         321.37
_chemical_name_systematic
4-[(2-Methoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazolidin-3(2H)-one
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.841(3)
_cell_length_b                   14.021(6)
_cell_length_c                   17.886(8)
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.828
_cell_measurement_theta_min      2.702
_cell_volume                     1715.6(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8948
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.132
_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     220
_refine_ls_number_reflns         1761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0392
_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/[σ²(Fo²)+(0.0269P)²+0.4536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1081
_reflns_number_total             1761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2117.cif
_cod_data_source_block           I
_cod_database_code               2211736
_cod_database_fobs_code          2211736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_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
N N1 -0.0054(4) 0.4880(2) 0.03294(16) 0.0556(8) Uani d . 1
N N2 -0.1758(4) 0.4385(2) 0.01076(16) 0.0556(8) Uani d . 1
N N3 0.0170(5) 0.26648(19) 0.13701(16) 0.0520(8) Uani d . 1
O O1 0.2640(4) 0.45152(17) 0.10595(14) 0.0661(8) Uani d . 1
O O2 0.5231(4) 0.24268(19) 0.24855(15) 0.0723(8) Uani d . 1
C C1 0.0999(6) 0.4304(2) 0.0830(2) 0.0508(10) Uani d . 1
C C2 -0.0216(5) 0.3487(2) 0.09611(18) 0.0456(9) Uani d . 1
C C3 -0.1871(5) 0.3584(2) 0.0539(2) 0.0486(9) Uani d . 1
C C4 -0.3431(5) 0.4977(3) -0.0100(2) 0.0769(13) Uani d . 1
H H4A -0.4478 0.4576 -0.0271 0.115 Uiso calc R 1
H H4B -0.3057 0.5406 -0.0493 0.115 Uiso calc R 1
H H4C -0.3857 0.5336 0.0326 0.115 Uiso calc R 1
C C5 -0.3600(5) 0.2954(3) 0.0509(2) 0.0717(12) Uani d . 1
H H5A -0.3344 0.2383 0.0788 0.108 Uiso calc R 1
H H5B -0.3876 0.2792 -0.0002 0.108 Uiso calc R 1
H H5C -0.4705 0.3279 0.0721 0.108 Uiso calc R 1
C C6 0.1777(6) 0.2586(2) 0.1731(2) 0.0510(9) Uani d . 1
H H6 0.2641 0.3098 0.1741 0.061 Uiso calc R 1
C C7 0.2282(5) 0.1715(3) 0.2125(2) 0.0508(10) Uani d . 1
C C8 0.4051(6) 0.1641(3) 0.2509(2) 0.0568(10) Uani d . 1
C C9 0.4540(6) 0.0814(3) 0.2893(2) 0.0675(12) Uani d . 1
H H9 0.5713 0.0775 0.3154 0.081 Uiso calc R 1
C C10 0.3272(7) 0.0054(3) 0.2882(2) 0.0795(13) Uani d . 1
H H10 0.3610 -0.0508 0.3127 0.095 Uiso calc R 1
C C11 0.1519(7) 0.0113(3) 0.2517(2) 0.0781(13) Uani d . 1
H H11 0.0656 -0.0400 0.2527 0.094 Uiso calc R 1
C C12 0.1034(6) 0.0931(3) 0.2134(2) 0.0660(11) Uani d . 1
H H12 -0.0146 0.0961 0.1877 0.079 Uiso calc R 1
C C13 0.6883(6) 0.2465(3) 0.2968(3) 0.0920(15) Uani d . 1
H H13A 0.6470 0.2359 0.3474 0.138 Uiso calc R 1
H H13B 0.7490 0.3080 0.2929 0.138 Uiso calc R 1
H H13C 0.7802 0.1980 0.2826 0.138 Uiso calc R 1
C C14 0.0883(5) 0.5496(3) -0.0192(2) 0.0546(10) Uani d . 1
C C15 0.0874(6) 0.5304(3) -0.0948(2) 0.0720(12) Uani d . 1
H H15 0.0225 0.4773 -0.1135 0.086 Uiso calc R 1
C C16 0.1854(8) 0.5920(4) -0.1421(3) 0.0973(16) Uani d . 1
H H16 0.1835 0.5812 -0.1934 0.117 Uiso calc R 1
C C17 0.2856(7) 0.6690(4) -0.1140(4) 0.107(2) Uani d . 1
H H17 0.3541 0.7090 -0.1461 0.128 Uiso calc R 1
C C18 0.2845(8) 0.6868(3) -0.0390(3) 0.0976(18) Uani d . 1
H H18 0.3511 0.7395 -0.0202 0.117 Uiso calc R 1
C C19 0.1849(6) 0.6270(3) 0.0092(3) 0.0734(12) Uani d . 1
H H19 0.1836 0.6392 0.0603 0.088 Uiso calc R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 N1 N2 108.6(3)
C1 N1 C14 122.4(3)
N2 N1 C14 119.0(3)
C3 N2 N1 107.0(3)
C3 N2 C4 124.5(3)
N1 N2 C4 116.0(3)
C6 N3 C2 120.0(3)
C8 O2 C13 118.7(3)
O1 C1 N1 122.8(3)
O1 C1 C2 131.7(4)
N1 C1 C2 105.4(3)
C3 C2 N3 122.0(3)
C3 C2 C1 108.1(3)
N3 C2 C1 129.7(3)
N2 C3 C2 110.2(3)
N2 C3 C5 121.1(3)
C2 C3 C5 128.6(3)
N2 C4 H4A 109.5
N2 C4 H4B 109.5
H4A C4 H4B 109.5
N2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N3 C6 C7 121.4(4)
N3 C6 H6 119.3
C7 C6 H6 119.3
C12 C7 C8 117.9(4)
C12 C7 C6 121.6(3)
C8 C7 C6 120.5(4)
O2 C8 C9 123.1(4)
O2 C8 C7 115.9(3)
C9 C8 C7 121.0(4)
C10 C9 C8 119.2(4)
C10 C9 H9 120.4
C8 C9 H9 120.4
C11 C10 C9 120.9(4)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C12 119.9(4)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C7 121.1(4)
C11 C12 H12 119.4
C7 C12 H12 119.4
O2 C13 H13A 109.5
O2 C13 H13B 109.5
H13A C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C19 C14 C15 121.3(4)
C19 C14 N1 117.1(4)
C15 C14 N1 121.5(4)
C14 C15 C16 118.4(4)
C14 C15 H15 120.8
C16 C15 H15 120.8
C17 C16 C15 120.6(5)
C17 C16 H16 119.7
C15 C16 H16 119.7
C18 C17 C16 120.1(5)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 120.2(5)
C17 C18 H18 119.9
C19 C18 H18 119.9
C14 C19 C18 119.3(4)
C14 C19 H19 120.4
C18 C19 H19 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.405(4)
N1 N2 1.413(4)
N1 C14 1.423(4)
N2 C3 1.365(4)
N2 C4 1.462(4)
N3 C6 1.280(4)
N3 C2 1.391(4)
O1 C1 1.231(4)
O2 C8 1.367(4)
O2 C13 1.423(4)
C1 C2 1.435(5)
C2 C3 1.368(4)
C3 C5 1.477(5)
C4 H4A 0.960
C4 H4B 0.960
C4 H4C 0.960
C5 H5A 0.960
C5 H5B 0.960
C5 H5C 0.960
C6 C7 1.452(5)
C6 H6 0.930
C7 C12 1.392(5)
C7 C8 1.395(5)
C8 C9 1.388(5)
C9 C10 1.375(5)
C9 H9 0.930
C10 C11 1.368(5)
C10 H10 0.930
C11 C12 1.377(5)
C11 H11 0.930
C12 H12 0.930
C13 H13A 0.960
C13 H13B 0.960
C13 H13C 0.960
C14 C19 1.367(5)
C14 C15 1.379(5)
C15 C16 1.382(5)
C15 H15 0.930
C16 C17 1.373(6)
C16 H16 0.930
C17 C18 1.364(7)
C17 H17 0.930
C18 C19 1.382(6)
C18 H18 0.930
C19 H19 0.930
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 C3 7.8(4)
C14 N1 N2 C3 154.3(3)
C1 N1 N2 C4 151.7(3)
C14 N1 N2 C4 -61.8(4)
N2 N1 C1 O1 172.9(3)
C14 N1 C1 O1 27.7(5)
N2 N1 C1 C2 -5.6(4)
C14 N1 C1 C2 -150.7(3)
C6 N3 C2 C3 176.8(3)
C6 N3 C2 C1 3.9(5)
O1 C1 C2 C3 -176.9(4)
N1 C1 C2 C3 1.4(4)
O1 C1 C2 N3 -3.2(7)
N1 C1 C2 N3 175.1(3)
N1 N2 C3 C2 -7.0(4)
C4 N2 C3 C2 -147.1(3)
N1 N2 C3 C5 173.3(3)
C4 N2 C3 C5 33.2(5)
N3 C2 C3 N2 -170.8(3)
C1 C2 C3 N2 3.5(4)
N3 C2 C3 C5 9.0(6)
C1 C2 C3 C5 -176.7(4)
C2 N3 C6 C7 -176.1(3)
N3 C6 C7 C12 -0.6(6)
N3 C6 C7 C8 179.4(3)
C13 O2 C8 C9 -10.4(6)
C13 O2 C8 C7 169.1(4)
C12 C7 C8 O2 179.9(3)
C6 C7 C8 O2 0.0(5)
C12 C7 C8 C9 -0.6(6)
C6 C7 C8 C9 179.5(4)
O2 C8 C9 C10 -179.5(4)
C7 C8 C9 C10 1.0(6)
C8 C9 C10 C11 -1.8(7)
C9 C10 C11 C12 2.0(7)
C10 C11 C12 C7 -1.5(7)
C8 C7 C12 C11 0.8(6)
C6 C7 C12 C11 -179.3(4)
C1 N1 C14 C19 -68.7(5)
N2 N1 C14 C19 149.6(3)
C1 N1 C14 C15 109.1(4)
N2 N1 C14 C15 -32.6(5)
C19 C14 C15 C16 -0.7(6)
N1 C14 C15 C16 -178.4(3)
C14 C15 C16 C17 1.7(7)
C15 C16 C17 C18 -1.8(8)
C16 C17 C18 C19 0.8(8)
C15 C14 C19 C18 -0.3(6)
N1 C14 C19 C18 177.5(4)
C17 C18 C19 C14 0.2(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655132
