#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/36/2213606.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_2213606
loop_
_publ_author_name
'Yan, Guo-Bing'
'Zhang, Chu-Niu'
'Yang, Ming-Hua'
_publ_section_title
1,5-Dimethyl-4-[2-(methylsulfanyl)benzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one
_journal_coeditor_code           WW2056
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2663
_journal_page_last               o2664
_journal_paper_doi               10.1107/S1600536807007453
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H19 N3 O S'
_chemical_formula_moiety         'C19 H19 N3 O S'
_chemical_formula_sum            'C19 H19 N3 O S'
_chemical_formula_weight         337.43
_chemical_name_systematic
;
1,5-Dimethyl-4-[2-(methylsulfanyl)benzylideneamino]-2-phenyl-1H-
pyrazol-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                   6.9535(9)
_cell_length_b                   12.9078(17)
_cell_length_c                   19.800(3)
_cell_measurement_reflns_used    5322
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.59
_cell_volume                     1777.1(4)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13405
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.88
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9375
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.343
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2166
_reflns_number_total             4287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2056.cif
_cod_data_source_block           I
_cod_database_code               2213606
_cod_database_fobs_code          2213606
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
C C13 0.881(4) 0.4068(13) 0.6920(11) 0.071(9) Uani d G 1
C C14 1.000(4) 0.4895(18) 0.6756(12) 0.067(9) Uani d G 1
H H14 1.1063 0.4792 0.6477 0.081 Uiso calc R 1
C C15 0.961(4) 0.5877(15) 0.7009(16) 0.104(15) Uani d G 1
H H15 1.0410 0.6431 0.6900 0.125 Uiso calc R 1
C C16 0.803(5) 0.6032(14) 0.7426(15) 0.101(15) Uani d G 1
H H16 0.7768 0.6689 0.7595 0.121 Uiso calc R 1
C C17 0.684(4) 0.5205(19) 0.7590(12) 0.082(11) Uani d G 1
H H17 0.5780 0.5308 0.7869 0.098 Uiso calc R 1
C C18 0.723(3) 0.4223(16) 0.7337(12) 0.078(10) Uani d GD 1
C C1 0.840(7) -0.195(3) 0.438(2) 0.083(11) Uani d D 1
H H1 0.7795 -0.2448 0.4117 0.099 Uiso calc R 1
C C2 0.825(6) -0.198(3) 0.507(2) 0.083(11) Uani d . 1
H H2 0.7522 -0.2495 0.5271 0.100 Uiso calc R 1
C C3 0.918(5) -0.125(3) 0.5461(19) 0.069(9) Uani d . 1
H H3 0.9111 -0.1286 0.5929 0.083 Uiso calc R 1
C C4 1.020(4) -0.046(2) 0.5155(16) 0.056(7) Uani d . 1
C C5 1.035(5) -0.043(2) 0.4460(17) 0.066(8) Uani d . 1
H H5 1.1051 0.0100 0.4254 0.079 Uiso calc R 1
C C6 0.946(6) -0.117(3) 0.408(2) 0.081(10) Uani d . 1
H H6 0.9564 -0.1146 0.3608 0.097 Uiso calc R 1
C C7 1.443(6) 0.015(3) 0.522(2) 0.083(11) Uani d . 1
H H7A 1.5580 0.0546 0.5299 0.125 Uiso calc R 1
H H7B 1.4385 -0.0073 0.4762 0.125 Uiso calc R 1
H H7C 1.4416 -0.0439 0.5517 0.125 Uiso calc R 1
C C8 1.454(7) 0.242(3) 0.562(2) 0.088(12) Uani d . 1
H H8A 1.4337 0.3039 0.5880 0.132 Uiso calc R 1
H H8B 1.4753 0.2600 0.5157 0.132 Uiso calc R 1
H H8C 1.5648 0.2060 0.5792 0.132 Uiso calc R 1
C C9 1.281(5) 0.174(2) 0.5675(16) 0.062(8) Uani d . 1
C C10 1.116(5) 0.192(2) 0.6020(15) 0.060(7) Uani d . 1
C C11 0.995(5) 0.100(2) 0.5961(16) 0.061(8) Uani d . 1
C C12 0.924(5) 0.301(2) 0.6644(17) 0.066(8) Uani d . 1
H H12 0.8398 0.2466 0.6720 0.079 Uiso calc R 1
C C19 0.380(10) 0.367(5) 0.797(3) 0.14(2) Uani d D 1
H H19A 0.4238 0.4110 0.8333 0.208 Uiso calc R 1
H H19B 0.3020 0.3125 0.8155 0.208 Uiso calc R 1
H H19C 0.3051 0.4073 0.7660 0.208 Uiso calc R 1
N N1 1.076(4) 0.287(2) 0.6311(14) 0.067(7) Uani d . 1
N N2 1.105(4) 0.031(2) 0.5579(14) 0.060(6) Uani d . 1
N N3 1.274(4) 0.081(2) 0.5367(14) 0.064(7) Uani d . 1
O O1 0.829(4) 0.081(2) 0.6151(14) 0.077(7) Uani d . 1
S S1 0.576(2) 0.3143(9) 0.7558(7) 0.105(5) Uani d D 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 0.0016 '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'
S S 0.1246 0.1234 '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 C13 C18 120.0 ?
C14 C13 C12 119.6(19) ?
C18 C13 C12 120.4(19) ?
C13 C14 C15 120.0 ?
C13 C14 H14 120.0 ?
C15 C14 H14 120.0 ?
C16 C15 C14 120.0 ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C17 C16 C15 120.0 ?
C17 C16 H16 120.0 ?
C15 C16 H16 120.0 ?
C16 C17 C18 120.0 ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.0 ?
C17 C18 C13 120.0 ?
C17 C18 S1 120.9(13) ?
C13 C18 S1 119.1(13) ?
C2 C1 C6 120(4) ?
C2 C1 H1 120.2 ?
C6 C1 H1 120.2 ?
C1 C2 C3 120(4) ?
C1 C2 H2 119.8 ?
C3 C2 H2 119.8 ?
C4 C3 C2 120(4) ?
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C3 C4 C5 120(3) ?
C3 C4 N2 118(3) ?
C5 C4 N2 122(3) ?
C6 C5 C4 120(3) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
C5 C6 C1 121(4) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
N3 C7 H7A 109.5 ?
N3 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
N3 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C9 C8 H8A 109.5 ?
C9 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C9 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N3 C9 C10 110(3) ?
N3 C9 C8 122(3) ?
C10 C9 C8 128(3) ?
C9 C10 N1 122(3) ?
C9 C10 C11 108(3) ?
N1 C10 C11 130(3) y
O1 C11 N2 123(3) ?
O1 C11 C10 132(3) ?
N2 C11 C10 104(3) ?
N1 C12 C13 119(3) ?
N1 C12 H12 120.3 ?
C13 C12 H12 120.3 ?
S1 C19 H19A 109.5 ?
S1 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
S1 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C12 N1 C10 121(3) y
C11 N2 N3 109(2) ?
C11 N2 C4 123(3) ?
N3 N2 C4 119(3) ?
C9 N3 N2 108(3) ?
C9 N3 C7 124(3) ?
N2 N3 C7 118(3) ?
C19 S1 C18 105(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C13 C14 1.3900 ?
C13 C18 1.3900 ?
C13 C12 1.50(3) ?
C14 C15 1.3900 ?
C14 H14 0.9300 ?
C15 C16 1.3900 ?
C15 H15 0.9300 ?
C16 C17 1.3900 ?
C16 H16 0.9300 ?
C17 C18 1.3900 ?
C17 H17 0.9300 ?
C18 S1 1.78(2) y
C1 C2 1.36(6) ?
C1 C6 1.39(6) ?
C1 H1 0.9300 ?
C2 C3 1.38(5) ?
C2 H2 0.9300 ?
C3 C4 1.38(5) ?
C3 H3 0.9300 ?
C4 C5 1.38(5) ?
C4 N2 1.43(4) ?
C5 C6 1.37(5) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 N3 1.47(5) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C9 1.49(5) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 N3 1.35(4) ?
C9 C10 1.36(5) ?
C10 N1 1.39(4) ?
C10 C11 1.45(4) ?
C11 O1 1.24(4) y
C11 N2 1.40(4) y
C12 N1 1.26(4) y
C12 H12 0.9300 ?
C19 S1 1.73(6) y
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
N2 N3 1.40(4) y
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
C12 H12 S1 . 0.93 2.62 3.03(4) 106.9
C12 H12 O1 . 0.93 2.41 3.07(4) 127.8
C7 H7A O1 1_655 0.96 2.55 3.37(5) 142.2
C8 H8C O1 1_655 0.96 2.54 3.49(6) 169.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655236
