#------------------------------------------------------------------------------
#$Date: 2023-03-06 12:13:13 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106846.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_8106846
loop_
_publ_author_name
'Barakat, Assem'
'Shivalingegowda, Naveen'
'Renuka, Nagamallu'
'Kariyappa, Ajay Kumar'
'Abdoh, Muneer'
'Warad, Ismail'
'Lokanath, Neratur Krishnappagowda'
_publ_section_title
;
 Crystal structure of
 3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              267
_journal_page_last               269
_journal_paper_doi               10.1515/ncrs-2015-0116
_journal_volume                  231
_journal_year                    2016
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C15 H15 N3 O S'
_chemical_formula_sum            'C15 H15 N3 O S'
_chemical_formula_weight         285.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.442(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2852(5)
_cell_length_b                   10.1649(5)
_cell_length_c                   14.7694(8)
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    296
_cell_measurement_theta_max      64.49
_cell_measurement_theta_min      4.66
_cell_volume                     1473.11(13)
_computing_cell_refinement       'SAINT [11]'
_computing_data_collection       'Apex2 [11]'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury [13]'
_computing_publication_material  'Mercury [13]'
_computing_structure_refinement  'SHELXL-2008 [12]'
_computing_structure_solution    'SHELXS-2008 [12]'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10384
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        64.49
_diffrn_reflns_theta_max         64.49
_diffrn_reflns_theta_min         4.66
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  0.664
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [11]'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Rectangle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0092(12)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_extinction_method     shelxl
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0449
_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/[σ²(Fo²)+(0.0749P)²+0.2683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2181
_reflns_number_total             2414
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            suppl_ncrs-2015-0116_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1473.12(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106846
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.31255(6) 0.68794(6) 0.87174(4) 1.000 0.0747(3) d . . .
O12 O Uani 0.94727(12) 0.58845(13) 0.88704(8) 1.000 0.0572(4) d . . .
N7 N Uani 0.60020(14) 0.64682(14) 0.85632(9) 1.000 0.0495(4) d . . .
N8 N Uani 0.72386(15) 0.63627(15) 0.83688(10) 1.000 0.0516(5) d . . .
N13 N Uani 0.81209(17) 0.5185(2) 0.97393(12) 1.000 0.0724(6) d . . .
C2 C Uani 0.39134(17) 0.76665(17) 0.79982(12) 1.000 0.0488(5) d . . .
C3 C Uani 0.3078(2) 0.8608(2) 0.74597(14) 1.000 0.0614(6) d . . .
C4 C Uani 0.1803(2) 0.8669(2) 0.76353(18) 1.000 0.0737(8) d . . .
C5 C Uani 0.1691(2) 0.7804(3) 0.8288(2) 1.000 0.0809(9) d . . .
C6 C Uani 0.52716(16) 0.73182(16) 0.79849(11) 1.000 0.0451(5) d . . .
C9 C Uani 0.72875(16) 0.71268(17) 0.75257(11) 1.000 0.0452(5) d . . .
C10 C Uani 0.59610(17) 0.79218(17) 0.73209(12) 1.000 0.0485(5) d . . .
C11 C Uani 0.83488(18) 0.58035(17) 0.90008(11) 1.000 0.0494(5) d . . .
C14 C Uani 0.73776(16) 0.62302(16) 0.67339(11) 1.000 0.0442(5) d . . .
C15 C Uani 0.8413(2) 0.6362(2) 0.63296(14) 1.000 0.0636(7) d . . .
C16 C Uani 0.8494(2) 0.5531(2) 0.56062(16) 1.000 0.0753(8) d . . .
C17 C Uani 0.7566(2) 0.4540(2) 0.52721(13) 1.000 0.0621(6) d . . .
C18 C Uani 0.6525(2) 0.44157(19) 0.56741(13) 1.000 0.0593(6) d . . .
C19 C Uani 0.64259(18) 0.52439(18) 0.63907(13) 1.000 0.0534(5) d . . .
C20 C Uani 0.7671(3) 0.3620(3) 0.44916(16) 1.000 0.0875(9) d . . .
H3 H Uiso 0.33220 0.91460 0.70280 1.000 0.0740 c R . .
H4 H Uiso 0.11140 0.92510 0.73280 1.000 0.0880 c R . .
H5 H Uiso 0.09180 0.77160 0.84850 1.000 0.0970 c R . .
H9 H Uiso 0.80720 0.77240 0.76980 1.000 0.0540 c R . .
H10A H Uiso 0.61470 0.88480 0.74580 1.000 0.0580 c R . .
H10B H Uiso 0.54100 0.78240 0.66650 1.000 0.0580 c R . .
H13A H Uiso 0.87840 0.48120 1.01590 1.000 0.0870 c R . .
H13B H Uiso 0.73120 0.51600 0.97930 1.000 0.0870 c R . .
H15 H Uiso 0.90650 0.70160 0.65440 1.000 0.0760 c R . .
H16 H Uiso 0.91980 0.56470 0.53390 1.000 0.0900 c R . .
H18 H Uiso 0.58760 0.37600 0.54580 1.000 0.0710 c R . .
H19 H Uiso 0.57100 0.51390 0.66470 1.000 0.0640 c R . .
H20A H Uiso 0.76510 0.41210 0.39370 1.000 0.1310 c R . .
H20B H Uiso 0.69170 0.30170 0.43420 1.000 0.1310 c R . .
H20C H Uiso 0.85100 0.31370 0.47010 1.000 0.1310 c R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 ' 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C5 91.68(11) . . . yes
N8 N7 C6 107.65(14) . . . yes
N7 N8 C9 113.40(13) . . . yes
N7 N8 C11 121.42(14) . . . yes
C9 N8 C11 124.17(15) . . . yes
H13A N13 H13B 120.00 . . . no
C11 N13 H13A 120.00 . . . no
C11 N13 H13B 120.00 . . . no
S1 C2 C3 110.79(15) . . . yes
S1 C2 C6 122.12(13) . . . yes
C3 C2 C6 127.09(17) . . . no
C2 C3 C4 112.29(18) . . . no
C3 C4 C5 112.9(2) . . . no
S1 C5 C4 112.31(17) . . . yes
N7 C6 C10 114.30(15) . . . yes
N7 C6 C2 121.95(15) . . . yes
C2 C6 C10 123.73(15) . . . no
N8 C9 C10 100.92(13) . . . yes
N8 C9 C14 111.14(14) . . . yes
C10 C9 C14 115.02(14) . . . no
C6 C10 C9 102.81(13) . . . no
N8 C11 N13 115.99(17) . . . yes
O12 C11 N13 124.13(17) . . . yes
O12 C11 N8 119.89(15) . . . yes
C9 C14 C15 120.92(16) . . . no
C9 C14 C19 121.33(15) . . . no
C15 C14 C19 117.75(16) . . . no
C14 C15 C16 120.64(19) . . . no
C15 C16 C17 121.9(2) . . . no
C16 C17 C20 121.8(2) . . . no
C16 C17 C18 117.31(18) . . . no
C18 C17 C20 120.9(2) . . . no
C17 C18 C19 121.37(18) . . . no
C14 C19 C18 121.01(18) . . . no
C2 C3 H3 124.00 . . . no
C4 C3 H3 124.00 . . . no
C3 C4 H4 123.00 . . . no
C5 C4 H4 124.00 . . . no
S1 C5 H5 124.00 . . . no
C4 C5 H5 124.00 . . . no
N8 C9 H9 110.00 . . . no
C10 C9 H9 110.00 . . . no
C14 C9 H9 110.00 . . . no
C6 C10 H10A 111.00 . . . no
C6 C10 H10B 111.00 . . . no
C9 C10 H10A 111.00 . . . no
C9 C10 H10B 111.00 . . . no
H10A C10 H10B 109.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C15 C16 H16 119.00 . . . no
C17 C16 H16 119.00 . . . no
C17 C18 H18 119.00 . . . no
C19 C18 H18 119.00 . . . no
C14 C19 H19 120.00 . . . no
C18 C19 H19 119.00 . . . no
C17 C20 H20A 110.00 . . . no
C17 C20 H20B 109.00 . . . no
C17 C20 H20C 109.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 109.00 . . . no
H20B C20 H20C 109.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7150(19) . . yes
S1 C5 1.703(3) . . yes
O12 C11 1.230(2) . . yes
N7 N8 1.389(2) . . yes
N7 C6 1.287(2) . . yes
N8 C9 1.481(2) . . yes
N8 C11 1.364(2) . . yes
N13 C11 1.339(2) . . yes
N13 H13B 0.8600 . . no
N13 H13A 0.8600 . . no
C2 C3 1.370(3) . . no
C2 C6 1.447(3) . . no
C3 C4 1.412(3) . . no
C4 C5 1.335(4) . . no
C6 C10 1.503(2) . . no
C9 C14 1.507(2) . . no
C9 C10 1.536(2) . . no
C14 C19 1.387(2) . . no
C14 C15 1.375(3) . . no
C15 C16 1.384(3) . . no
C16 C17 1.374(3) . . no
C17 C18 1.377(3) . . no
C17 C20 1.513(3) . . no
C18 C19 1.380(3) . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C9 H9 0.9800 . . no
C10 H10A 0.9700 . . no
C10 H10B 0.9700 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C18 H18 0.9300 . . no
C19 H19 0.9300 . . no
C20 H20A 0.9600 . . no
C20 H20B 0.9600 . . no
C20 H20C 0.9600 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N13 H13A O12 0.8600 2.0600 2.912(2) 172.00 3_767 yes
N13 H13B N7 0.8600 2.3300 2.683(2) 105.00 . yes
C5 H5 O12 0.9300 2.5500 3.306(3) 139.00 1_455 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 S1 C2 C3 0.37(17) . . . . no
C5 S1 C2 C6 -178.64(17) . . . . no
C2 S1 C5 C4 -0.2(2) . . . . no
C6 N7 N8 C9 -5.67(18) . . . . no
C6 N7 N8 C11 163.27(15) . . . . no
N8 N7 C6 C2 -179.83(15) . . . . no
N8 N7 C6 C10 -0.96(19) . . . . no
C11 N8 C9 C14 78.3(2) . . . . no
C9 N8 C11 N13 177.85(16) . . . . no
N7 N8 C11 O12 -170.01(15) . . . . no
N7 N8 C9 C10 9.28(17) . . . . no
C11 N8 C9 C10 -159.30(15) . . . . no
N7 N8 C11 N13 10.1(2) . . . . no
N7 N8 C9 C14 -113.17(15) . . . . no
C9 N8 C11 O12 -2.3(3) . . . . no
C3 C2 C6 N7 175.78(18) . . . . no
C6 C2 C3 C4 178.52(18) . . . . no
C3 C2 C6 C10 -3.0(3) . . . . no
S1 C2 C6 N7 -5.4(2) . . . . no
S1 C2 C6 C10 175.86(13) . . . . no
S1 C2 C3 C4 -0.4(2) . . . . no
C2 C3 C4 C5 0.3(3) . . . . no
C3 C4 C5 S1 0.0(3) . . . . no
C2 C6 C10 C9 -174.53(15) . . . . no
N7 C6 C10 C9 6.62(19) . . . . no
C10 C9 C14 C15 121.31(18) . . . . no
C10 C9 C14 C19 -58.9(2) . . . . no
N8 C9 C14 C19 55.0(2) . . . . no
N8 C9 C10 C6 -8.71(16) . . . . no
C14 C9 C10 C6 110.99(15) . . . . no
N8 C9 C14 C15 -124.82(18) . . . . no
C9 C14 C15 C16 179.65(18) . . . . no
C19 C14 C15 C16 -0.1(3) . . . . no
C9 C14 C19 C18 -179.14(16) . . . . no
C15 C14 C19 C18 0.6(3) . . . . no
C14 C15 C16 C17 -0.8(3) . . . . no
C15 C16 C17 C18 1.2(3) . . . . no
C15 C16 C17 C20 -179.0(2) . . . . no
C16 C17 C18 C19 -0.7(3) . . . . no
C20 C17 C18 C19 179.5(2) . . . . no
C17 C18 C19 C14 -0.2(3) . . . . no
