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#$Date: 2022-11-10 12:38:16 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106066.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_8106066
loop_
_publ_author_name
'Yang, Peng'
'Yan, Ling-Ling'
'Cai, Hong-Xin'
_publ_section_title
;
 Crystal structure of
 3-(3-dimethylaminopropyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one,
 C13H17N3OS
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              117
_journal_page_last               118
_journal_paper_doi               10.1515/ncrs-2017-0203
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C13 H17 N3 O S'
_chemical_formula_weight         263.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.698(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3721(9)
_cell_length_b                   15.3783(14)
_cell_length_c                   9.1684(9)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.43
_cell_measurement_theta_min      2.06
_cell_volume                     1312.4(2)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7855
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.558
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0371
_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)+(0.0200P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2259
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0203_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106066
_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   0.963
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.07009(5) 0.10208(3) 0.34148(5) 0.05670(15) Uani 1 1 d . . . . .
O1 O 0.34313(13) 0.09853(8) 0.83937(12) 0.0617(3) Uani 1 1 d . . . . .
N1 N 0.25681(12) -0.01528(8) 0.44693(13) 0.0387(3) Uani 1 1 d . . . . .
H1A H 0.239607 -0.038524 0.361371 0.046 Uiso 1 1 calc R U . . .
N2 N 0.21947(12) 0.09631(8) 0.60980(13) 0.0385(3) Uani 1 1 d . . . . .
N3 N -0.17075(13) 0.10887(9) 0.82569(14) 0.0465(3) Uani 1 1 d . . . . .
C1 C 0.35413(14) -0.05643(9) 0.54872(15) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.42504(16) -0.13200(10) 0.51235(18) 0.0447(4) Uani 1 1 d . . . . .
H2A H 0.407333 -0.155375 0.418431 0.054 Uiso 1 1 calc R U . . .
C3 C 0.52112(17) -0.17150(11) 0.6164(2) 0.0517(4) Uani 1 1 d . . . . .
H3A H 0.568438 -0.221698 0.592227 0.062 Uiso 1 1 calc R U . . .
C4 C 0.54852(17) -0.13748(12) 0.7572(2) 0.0564(4) Uani 1 1 d . . . . .
H4A H 0.612837 -0.165151 0.827115 0.068 Uiso 1 1 calc R U . . .
C5 C 0.48035(16) -0.06301(12) 0.79260(17) 0.0506(4) Uani 1 1 d . . . . .
H5A H 0.498752 -0.040101 0.886798 0.061 Uiso 1 1 calc R U . . .
C6 C 0.38318(14) -0.02103(10) 0.68818(16) 0.0396(3) Uani 1 1 d . . . . .
C7 C 0.31673(15) 0.06085(10) 0.72224(16) 0.0428(3) Uani 1 1 d . . . . .
C8 C 0.18701(15) 0.05862(9) 0.47217(16) 0.0389(3) Uani 1 1 d . . . . .
C9 C 0.15533(17) 0.18161(9) 0.63925(18) 0.0478(4) Uani 1 1 d . . . . .
H9A H 0.159018 0.218666 0.554156 0.057 Uiso 1 1 calc R U . . .
H9B H 0.213236 0.208747 0.721415 0.057 Uiso 1 1 calc R U . . .
C10 C 0.00138(17) 0.17670(10) 0.67355(18) 0.0470(4) Uani 1 1 d . . . . .
H10A H -0.033938 0.235337 0.684689 0.056 Uiso 1 1 calc R U . . .
H10B H -0.056817 0.150379 0.590756 0.056 Uiso 1 1 calc R U . . .
C11 C -0.01826(15) 0.12554(10) 0.81037(17) 0.0452(4) Uani 1 1 d . . . . .
H11A H 0.031728 0.070439 0.807565 0.054 Uiso 1 1 calc R U . . .
H11B H 0.024736 0.157414 0.895679 0.054 Uiso 1 1 calc R U . . .
C12 C -0.18215(19) 0.04915(14) 0.94797(19) 0.0646(5) Uani 1 1 d . . . . .
H12A H -0.137344 -0.005151 0.928813 0.097 Uiso 1 1 calc R U . . .
H12B H -0.281613 0.039414 0.958474 0.097 Uiso 1 1 calc R U . . .
H12C H -0.134967 0.073981 1.036863 0.097 Uiso 1 1 calc R U . . .
C13 C -0.2473(2) 0.18967(14) 0.8510(2) 0.0724(6) Uani 1 1 d . . . . .
H13A H -0.242958 0.228214 0.769320 0.109 Uiso 1 1 calc R U . . .
H13B H -0.203181 0.216974 0.939139 0.109 Uiso 1 1 calc R U . . .
H13C H -0.345825 0.176703 0.861290 0.109 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 124.58(12) . .
C8 N1 H1A 117.7 . .
C1 N1 H1A 117.7 . .
C8 N2 C7 124.00(12) . .
C8 N2 C9 118.98(12) . .
C7 N2 C9 116.92(12) . .
C12 N3 C13 109.25(14) . .
C12 N3 C11 109.90(12) . .
C13 N3 C11 111.42(13) . .
N1 C1 C6 119.11(13) . .
N1 C1 C2 120.99(13) . .
C6 C1 C2 119.89(13) . .
C3 C2 C1 119.52(15) . .
C3 C2 H2A 120.2 . .
C1 C2 H2A 120.2 . .
C2 C3 C4 120.92(16) . .
C2 C3 H3A 119.5 . .
C4 C3 H3A 119.5 . .
C5 C4 C3 119.65(15) . .
C5 C4 H4A 120.2 . .
C3 C4 H4A 120.2 . .
C4 C5 C6 120.55(16) . .
C4 C5 H5A 119.7 . .
C6 C5 H5A 119.7 . .
C1 C6 C5 119.44(15) . .
C1 C6 C7 119.65(13) . .
C5 C6 C7 120.87(14) . .
O1 C7 N2 120.63(15) . .
O1 C7 C6 123.51(14) . .
N2 C7 C6 115.86(13) . .
N1 C8 N2 116.70(13) . .
N1 C8 S1 120.50(11) . .
N2 C8 S1 122.79(11) . .
N2 C9 C10 114.25(12) . .
N2 C9 H9A 108.7 . .
C10 C9 H9A 108.7 . .
N2 C9 H9B 108.7 . .
C10 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
C11 C10 C9 114.20(13) . .
C11 C10 H10A 108.7 . .
C9 C10 H10A 108.7 . .
C11 C10 H10B 108.7 . .
C9 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
N3 C11 C10 112.52(12) . .
N3 C11 H11A 109.1 . .
C10 C11 H11A 109.1 . .
N3 C11 H11B 109.1 . .
C10 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
N3 C12 H12A 109.5 . .
N3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N3 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N3 C13 H13A 109.5 . .
N3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 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 1.6663(15) .
O1 C7 1.2200(17) .
N1 C8 1.3448(18) .
N1 C1 1.3801(17) .
N1 H1A 0.8600 .
N2 C8 1.3897(18) .
N2 C7 1.4042(19) .
N2 C9 1.4807(18) .
N3 C12 1.463(2) .
N3 C13 1.467(2) .
N3 C11 1.4748(19) .
C1 C6 1.387(2) .
C1 C2 1.398(2) .
C2 C3 1.375(2) .
C2 H2A 0.9300 .
C3 C4 1.389(2) .
C3 H3A 0.9300 .
C4 C5 1.369(2) .
C4 H4A 0.9300 .
C5 C6 1.400(2) .
C5 H5A 0.9300 .
C6 C7 1.455(2) .
C9 C10 1.514(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.510(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 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 N3 0.86 2.07 2.9153(17) 169.1 3_556 yes
