#------------------------------------------------------------------------------
#$Date: 2022-11-25 12:21:30 +0200 (Fri, 25 Nov 2022) $
#$Revision: 279567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106261.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_8106261
loop_
_publ_author_name
'Wu, Hao'
'Zong, Hai-Tao'
_publ_section_title
;
 Crystal structure of 3-methyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one,
 C9H8N2OS
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              685
_journal_page_last               686
_journal_paper_doi               10.1515/ncrs-2018-0013
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C9 H8 N2 O S'
_chemical_formula_weight         192.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 108.818(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.273(5)
_cell_length_b                   9.026(2)
_cell_length_c                   8.2852(19)
_cell_measurement_reflns_used    698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.46
_cell_measurement_theta_min      2.12
_cell_volume                     1718.2(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.773
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.968
_exptl_transmission_factor_min   0.955
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0538P)²+0.2459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                972
_reflns_number_total             1521
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0013_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106261
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.00345(3) 0.23770(8) 0.50042(10) 0.0506(3) Uani 1 1 d . . . . .
N1 N 0.07239(10) 0.0494(3) 0.7138(3) 0.0402(6) Uani 1 1 d . . . . .
H1A H 0.049342 -0.016256 0.652344 0.048 Uiso 1 1 calc R U . . .
N2 N 0.09650(10) 0.2956(2) 0.7733(3) 0.0401(6) Uani 1 1 d . . . . .
O1 O 0.17137(9) 0.3590(3) 1.0094(3) 0.0642(7) Uani 1 1 d . . . . .
C1 C 0.11906(11) -0.0005(3) 0.8480(3) 0.0346(7) Uani 1 1 d . . . . .
C2 C 0.12996(12) -0.1515(3) 0.8753(4) 0.0449(8) Uani 1 1 d . . . . .
H2B H 0.105378 -0.220816 0.804626 0.054 Uiso 1 1 calc R U . . .
C3 C 0.17737(13) -0.1965(4) 1.0075(4) 0.0508(9) Uani 1 1 d . . . . .
H3A H 0.184859 -0.297194 1.026413 0.061 Uiso 1 1 calc R U . . .
C4 C 0.21444(13) -0.0939(4) 1.1139(4) 0.0524(9) Uani 1 1 d . . . . .
H4A H 0.246395 -0.126055 1.203486 0.063 Uiso 1 1 calc R U . . .
C5 C 0.20375(13) 0.0552(4) 1.0865(4) 0.0487(8) Uani 1 1 d . . . . .
H5A H 0.228695 0.123861 1.157116 0.058 Uiso 1 1 calc R U . . .
C6 C 0.15574(11) 0.1036(3) 0.9533(3) 0.0373(7) Uani 1 1 d . . . . .
C7 C 0.14351(13) 0.2598(3) 0.9208(4) 0.0426(8) Uani 1 1 d . . . . .
C8 C 0.06008(12) 0.1923(3) 0.6716(4) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.08540(15) 0.4535(3) 0.7362(4) 0.0583(10) Uani 1 1 d . . . . .
H9A H 0.114528 0.510979 0.818375 0.087 Uiso 1 1 calc R U . . .
H9B H 0.086757 0.474469 0.623938 0.087 Uiso 1 1 calc R U . . .
H9C H 0.047656 0.478669 0.741983 0.087 Uiso 1 1 calc R U . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N1 C1 125.3(2) . .
C8 N1 H1A 117.4 . .
C1 N1 H1A 117.4 . .
C8 N2 C7 123.8(2) . .
C8 N2 C9 119.6(2) . .
C7 N2 C9 116.5(2) . .
N1 C1 C6 118.5(3) . .
N1 C1 C2 120.9(3) . .
C6 C1 C2 120.6(2) . .
C3 C2 C1 119.1(3) . .
C3 C2 H2B 120.4 . .
C1 C2 H2B 120.4 . .
C2 C3 C4 121.0(3) . .
C2 C3 H3A 119.5 . .
C4 C3 H3A 119.5 . .
C5 C4 C3 119.9(3) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
C4 C5 C6 120.2(3) . .
C4 C5 H5A 119.9 . .
C6 C5 H5A 119.9 . .
C1 C6 C5 119.2(3) . .
C1 C6 C7 119.3(3) . .
C5 C6 C7 121.5(3) . .
O1 C7 N2 119.3(3) . .
O1 C7 C6 124.4(3) . .
N2 C7 C6 116.3(2) . .
N1 C8 N2 116.6(2) . .
N1 C8 S1 120.5(2) . .
N2 C8 S1 122.9(2) . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C8 1.676(3) .
N1 C8 1.345(3) .
N1 C1 1.382(3) .
N1 H1A 0.8600 .
N2 C8 1.371(3) .
N2 C7 1.414(4) .
N2 C9 1.465(3) .
O1 C7 1.216(3) .
C1 C6 1.391(4) .
C1 C2 1.393(4) .
C2 C3 1.370(4) .
C2 H2B 0.9300 .
C3 C4 1.390(4) .
C3 H3A 0.9300 .
C4 C5 1.376(4) .
C4 H4A 0.9300 .
C5 C6 1.392(4) .
C5 H5A 0.9300 .
C6 C7 1.448(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
N1 H1A S1 0.86 2.49 3.339(2) 169.9 5_556 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
C8 N1 C1 C6 2.4(4) . . . .
C8 N1 C1 C2 -176.2(3) . . . .
N1 C1 C2 C3 178.6(3) . . . .
C6 C1 C2 C3 0.0(4) . . . .
C1 C2 C3 C4 0.0(5) . . . .
C2 C3 C4 C5 -0.2(5) . . . .
C3 C4 C5 C6 0.5(5) . . . .
N1 C1 C6 C5 -178.4(3) . . . .
C2 C1 C6 C5 0.2(4) . . . .
N1 C1 C6 C7 0.9(4) . . . .
C2 C1 C6 C7 179.5(3) . . . .
C4 C5 C6 C1 -0.4(5) . . . .
C4 C5 C6 C7 -179.7(3) . . . .
C8 N2 C7 O1 -175.5(3) . . . .
C9 N2 C7 O1 1.0(4) . . . .
C8 N2 C7 C6 5.8(4) . . . .
C9 N2 C7 C6 -177.7(3) . . . .
C1 C6 C7 O1 176.7(3) . . . .
C5 C6 C7 O1 -4.0(5) . . . .
C1 C6 C7 N2 -4.6(4) . . . .
C5 C6 C7 N2 174.7(3) . . . .
C1 N1 C8 N2 -1.5(4) . . . .
C1 N1 C8 S1 177.5(2) . . . .
C7 N2 C8 N1 -2.8(4) . . . .
C9 N2 C8 N1 -179.3(3) . . . .
C7 N2 C8 S1 178.2(2) . . . .
C9 N2 C8 S1 1.7(4) . . . .
