#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/22/2212275.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_2212275
loop_
_publ_author_name
'Yun-Fa Zheng'
'Chun-Niu Zhang'
'Ming-Hua Yang'
_publ_section_title
4-(3-Bromothien-2-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
_journal_coeditor_code           LH2257
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o685
_journal_page_last               o686
_journal_paper_doi               10.1107/S1600536806051725
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H14 Br N3 O S'
_chemical_formula_moiety         'C16 H14 Br N3 O S'
_chemical_formula_sum            'C16 H14 Br N3 O S'
_chemical_formula_weight         376.27
_chemical_name_systematic
;
4-(3-Bromothien-2-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.003(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2439(12)
_cell_length_b                   7.3436(10)
_cell_length_c                   24.218(3)
_cell_measurement_reflns_used    2507
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.55
_cell_volume                     1613.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8225
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_T_max  0.6606
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.6288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2328
_reflns_number_total             2891
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2257.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/c'
_cod_database_code               2212275
_cod_database_fobs_code          2212275
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br Br1 -0.06419(4) 0.57513(5) 1.227487(13) 0.06069(15) Uani d . 1
S S1 0.08085(8) 0.53046(10) 1.12277(3) 0.0463(2) Uani d . 1
O O1 0.2209(2) 0.8255(3) 0.91970(8) 0.0491(5) Uani d . 1
N N1 0.2148(2) 0.5385(3) 1.01538(9) 0.0379(5) Uani d . 1
N N2 0.3583(2) 0.6002(3) 0.88747(9) 0.0377(5) Uani d . 1
N N3 0.4222(2) 0.4349(3) 0.90920(9) 0.0370(5) Uani d . 1
C C1 -0.0174(3) 0.6646(4) 1.16060(12) 0.0442(7) Uani d . 1
C C2 -0.0534(3) 0.8283(4) 1.13710(12) 0.0485(7) Uani d . 1
H H2 -0.1065 0.9171 1.1521 0.058 Uiso calc R 1
C C3 0.0000(4) 0.8470(4) 1.08678(12) 0.0515(8) Uani d . 1
H H3 -0.0149 0.9514 1.0647 0.062 Uiso calc R 1
C C4 0.0754(3) 0.6996(4) 1.07309(11) 0.0425(7) Uani d . 1
C C5 0.1408(3) 0.6800(4) 1.02402(12) 0.0445(7) Uani d . 1
H H5 0.1290 0.7733 0.9976 0.053 Uiso calc R 1
C C6 0.2772(3) 0.5334(3) 0.96708(11) 0.0350(6) Uani d . 1
C C7 0.2748(3) 0.6718(4) 0.92509(11) 0.0370(6) Uani d . 1
C C8 0.3623(3) 0.3918(3) 0.95453(11) 0.0352(6) Uani d . 1
C C9 0.4306(3) 0.7111(4) 0.85313(11) 0.0379(6) Uani d . 1
C C10 0.3427(4) 0.8133(4) 0.81137(11) 0.0470(7) Uani d . 1
H H10 0.2406 0.8035 0.8055 0.056 Uiso calc R 1
C C11 0.4087(5) 0.9294(4) 0.77876(13) 0.0598(9) Uani d . 1
H H11 0.3509 0.9991 0.7509 0.072 Uiso calc R 1
C C12 0.5592(5) 0.9421(5) 0.78738(15) 0.0668(11) Uani d . 1
H H12 0.6032 1.0204 0.7653 0.080 Uiso calc R 1
C C13 0.6457(4) 0.8394(5) 0.82859(14) 0.0621(9) Uani d . 1
H H13 0.7478 0.8480 0.8339 0.075 Uiso calc R 1
C C14 0.5819(3) 0.7235(4) 0.86225(12) 0.0464(7) Uani d . 1
H H14 0.6401 0.6554 0.8904 0.056 Uiso calc R 1
C C15 0.3905(3) 0.2124(4) 0.98264(12) 0.0461(7) Uani d . 1
H H15A 0.4949 0.1921 0.9926 0.069 Uiso calc R 1
H H15B 0.3462 0.1181 0.9575 0.069 Uiso calc R 1
H H15C 0.3488 0.2108 1.0160 0.069 Uiso calc R 1
C C16 0.4627(4) 0.3039(4) 0.86962(12) 0.0520(8) Uani d . 1
H H16A 0.3772 0.2732 0.8420 0.078 Uiso calc R 1
H H16B 0.5014 0.1960 0.8895 0.078 Uiso calc R 1
H H16C 0.5363 0.3563 0.8513 0.078 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 0.0016 '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'
Br Br -0.2901 2.4595 '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
C1 S1 C4 90.63(14) n
C5 N1 C6 118.4(2) n
C7 N2 N3 108.9(2) n
C7 N2 C9 123.0(2) ?
N3 N2 C9 120.2(2) n
C8 N3 N2 107.2(2) ?
C8 N3 C16 125.0(2) ?
N2 N3 C16 117.8(2) ?
C2 C1 S1 113.6(2) n
C2 C1 Br1 126.9(2) n
S1 C1 Br1 119.53(17) n
C1 C2 C3 110.8(3) ?
C1 C2 H2 124.6 ?
C3 C2 H2 124.6 ?
C4 C3 C2 114.5(3) ?
C4 C3 H3 122.8 ?
C2 C3 H3 122.8 ?
C3 C4 C5 126.6(3) ?
C3 C4 S1 110.6(2) ?
C5 C4 S1 122.9(2) ?
N1 C5 C4 122.5(3) n
N1 C5 H5 118.8 ?
C4 C5 H5 118.8 ?
C8 C6 N1 123.4(2) n
C8 C6 C7 108.1(2) ?
N1 C6 C7 128.3(2) ?
O1 C7 N2 122.4(2) n
O1 C7 C6 132.5(2) n
N2 C7 C6 105.0(2) ?
N3 C8 C6 110.0(2) ?
N3 C8 C15 121.0(2) ?
C6 C8 C15 129.0(2) ?
C14 C9 C10 121.1(3) ?
C14 C9 N2 121.4(2) ?
C10 C9 N2 117.4(3) ?
C11 C10 C9 119.2(3) ?
C11 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
C12 C11 C10 120.1(3) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C11 C12 C13 120.3(3) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C12 C13 C14 120.6(3) ?
C12 C13 H13 119.7 ?
C14 C13 H13 119.7 ?
C9 C14 C13 118.6(3) ?
C9 C14 H14 120.7 ?
C13 C14 H14 120.7 ?
C8 C15 H15A 109.5 ?
C8 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C8 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N3 C16 H16A 109.5 ?
N3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
N3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.873(3) ?
S1 C1 1.718(3) ?
S1 C4 1.723(3) ?
O1 C7 1.231(3) ?
N1 C5 1.283(3) n
N1 C6 1.400(3) n
N2 C7 1.404(3) n
N2 N3 1.407(3) n
N2 C9 1.419(3) n
N3 C8 1.358(3) n
N3 C16 1.456(3) n
C1 C2 1.344(4) ?
C2 C3 1.407(4) ?
C2 H2 0.9300 ?
C3 C4 1.362(4) ?
C3 H3 0.9300 ?
C4 C5 1.440(4) n
C5 H5 0.9300 ?
C6 C8 1.372(4) ?
C6 C7 1.435(4) ?
C8 C15 1.483(4) ?
C9 C14 1.377(4) ?
C9 C10 1.390(4) ?
C10 C11 1.381(4) ?
C10 H10 0.9300 ?
C11 C12 1.370(5) n
C11 H11 0.9300 ?
C12 C13 1.378(5) ?
C12 H12 0.9300 ?
C13 C14 1.386(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C7 N2 N3 C8 8.8(3)
C9 N2 N3 C8 158.6(2)
C7 N2 N3 C16 156.2(2)
C9 N2 N3 C16 -54.0(3)
C4 S1 C1 C2 0.3(3)
C4 S1 C1 Br1 179.93(18)
S1 C1 C2 C3 -0.1(4)
Br1 C1 C2 C3 -179.7(2)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 179.4(3)
C2 C3 C4 S1 0.5(4)
C1 S1 C4 C3 -0.4(2)
C1 S1 C4 C5 -179.4(3)
C6 N1 C5 C4 -178.5(3)
C3 C4 C5 N1 177.4(3)
S1 C4 C5 N1 -3.8(4)
C5 N1 C6 C8 177.9(3)
C5 N1 C6 C7 2.5(4)
N3 N2 C7 O1 171.4(3)
C9 N2 C7 O1 22.6(4)
N3 N2 C7 C6 -6.4(3)
C9 N2 C7 C6 -155.2(2)
C8 C6 C7 O1 -175.8(3)
N1 C6 C7 O1 0.1(5)
C8 C6 C7 N2 1.7(3)
N1 C6 C7 N2 177.6(3)
N2 N3 C8 C6 -7.7(3)
C16 N3 C8 C6 -152.1(3)
N2 N3 C8 C15 171.5(2)
C16 N3 C8 C15 27.1(4)
N1 C6 C8 N3 -172.4(2)
C7 C6 C8 N3 3.8(3)
N1 C6 C8 C15 8.5(5)
C7 C6 C8 C15 -175.4(3)
C7 N2 C9 C14 110.9(3)
N3 N2 C9 C14 -34.7(4)
C7 N2 C9 C10 -66.4(3)
N3 N2 C9 C10 148.1(2)
C14 C9 C10 C11 -0.3(4)
N2 C9 C10 C11 177.0(2)
C9 C10 C11 C12 0.5(4)
C10 C11 C12 C13 -0.1(5)
C11 C12 C13 C14 -0.7(5)
C10 C9 C14 C13 -0.5(4)
N2 C9 C14 C13 -177.6(3)
C12 C13 C14 C9 0.9(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655161
