#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/39/2233900.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_2233900
loop_
_publ_author_name
'Al-Salahi, Rashad'
'Al-Omar, Mohamed'
'El-Subbagh, Hussein'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 3-Benzyl-6-methyl-2-sulfanylidene-2,3-dihydroquinazolin-4(1H)-one
;
_journal_coeditor_code           IS5070
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o717
_journal_page_last               o718
_journal_paper_doi               10.1107/S1600536812006009
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C16 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.35
_chemical_name_systematic
;
3-Benzyl-6-methyl-2-sulfanylidene-2,3-dihydroquinazolin-4(1H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.532(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.2438(18)
_cell_length_b                   5.1618(5)
_cell_length_c                   24.4265(17)
_cell_measurement_reflns_used    339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.53
_cell_measurement_theta_min      3.89
_cell_volume                     2843.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9528
_diffrn_reflns_theta_full        69.83
_diffrn_reflns_theta_max         69.83
_diffrn_reflns_theta_min         3.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.988
_exptl_absorpt_correction_T_max  0.8900
_exptl_absorpt_correction_T_min  0.2891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                1421
_reflns_number_total             2592
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5070.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233900
_cod_database_fobs_code          2233900
loop_
_symmetry_equiv_pos_as_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_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
_atom_site_symmetry_multiplicity
S S1 0.22029(4) 0.1447(2) 0.07055(4) 0.0718(3) Uani d . 1 1
N N1 0.17921(10) 0.4985(6) -0.01167(11) 0.0630(7) Uani d . 1 1
H H1A 0.2097 0.4590 -0.0199 0.076 Uiso calc R 1 1
N N2 0.12318(10) 0.4401(5) 0.04598(11) 0.0574(7) Uani d . 1 1
O O1 0.04534(10) 0.7057(5) 0.03541(11) 0.0747(7) Uani d . 1 1
C C1 0.17206(13) 0.3706(7) 0.03308(14) 0.0594(8) Uani d . 1 1
C C2 0.08423(13) 0.6424(7) 0.01808(14) 0.0600(8) Uani d . 1 1
C C3 0.09395(12) 0.7664(7) -0.03127(13) 0.0585(8) Uani d . 1 1
C C4 0.05611(13) 0.9575(7) -0.06444(14) 0.0630(9) Uani d . 1 1
H H4A 0.0243 1.0100 -0.0544 0.076 Uiso calc R 1 1
C C5 0.06438(15) 1.0717(7) -0.11196(15) 0.0691(9) Uani d . 1 1
C C6 0.11382(16) 0.9891(8) -0.12434(16) 0.0763(10) Uani d . 1 1
H H6A 0.1206 1.0638 -0.1559 0.092 Uiso calc R 1 1
C C7 0.15210(15) 0.8048(7) -0.09221(15) 0.0715(10) Uani d . 1 1
H H7A 0.1848 0.7578 -0.1013 0.086 Uiso calc R 1 1
C C8 0.14201(13) 0.6879(7) -0.04573(14) 0.0578(8) Uani d . 1 1
C C9 0.10920(14) 0.2997(7) 0.09172(15) 0.0657(9) Uani d . 1 1
H H9A 0.1263 0.1276 0.0958 0.079 Uiso calc R 1 1
H H9B 0.0665 0.2799 0.0788 0.079 Uiso calc R 1 1
C C10 0.13111(14) 0.4281(7) 0.15093(14) 0.0641(9) Uani d . 1 1
C C11 0.1103(2) 0.3376(10) 0.1930(2) 0.0988(15) Uani d . 1 1
H H11A 0.0831 0.2022 0.1840 0.119 Uiso calc R 1 1
C C12 0.1298(3) 0.4483(15) 0.2483(2) 0.131(2) Uani d . 1 1
H H12A 0.1144 0.3902 0.2758 0.157 Uiso calc R 1 1
C C13 0.1710(3) 0.6401(16) 0.2634(2) 0.133(2) Uani d . 1 1
H H13A 0.1854 0.7057 0.3015 0.160 Uiso calc R 1 1
C C14 0.1912(2) 0.7364(11) 0.2216(2) 0.1082(15) Uani d . 1 1
H H14A 0.2179 0.8737 0.2306 0.130 Uiso calc R 1 1
C C15 0.17129(17) 0.6268(8) 0.16567(16) 0.0783(11) Uani d . 1 1
H H15A 0.1856 0.6898 0.1377 0.094 Uiso calc R 1 1
C C16 0.02217(18) 1.2711(9) -0.14931(18) 0.0893(12) Uani d . 1 1
H H16B -0.0064 1.3143 -0.1321 0.134 Uiso calc R 1 1
H H16A 0.0021 1.2027 -0.1881 0.134 Uiso calc R 1 1
H H16C 0.0438 1.4238 -0.1516 0.134 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C1 N1 C8 126.0(2)
C1 N1 H1A 117.0
C8 N1 H1A 117.0
C1 N2 C2 124.2(3)
C1 N2 C9 120.1(3)
C2 N2 C9 115.7(2)
N1 C1 N2 115.9(3)
N1 C1 S1 121.1(2)
N2 C1 S1 123.0(2)
O1 C2 N2 120.1(3)
O1 C2 C3 123.6(3)
N2 C2 C3 116.3(2)
C4 C3 C8 119.5(3)
C4 C3 C2 121.5(3)
C8 C3 C2 119.0(3)
C5 C4 C3 121.7(3)
C5 C4 H4A 119.1
C3 C4 H4A 119.1
C4 C5 C6 116.7(3)
C4 C5 C16 121.8(3)
C6 C5 C16 121.5(3)
C7 C6 C5 122.9(3)
C7 C6 H6A 118.5
C5 C6 H6A 118.5
C6 C7 C8 119.3(3)
C6 C7 H7A 120.3
C8 C7 H7A 120.3
N1 C8 C7 122.0(3)
N1 C8 C3 118.3(3)
C7 C8 C3 119.7(3)
N2 C9 C10 114.6(3)
N2 C9 H9A 108.6
C10 C9 H9A 108.6
N2 C9 H9B 108.6
C10 C9 H9B 108.6
H9A C9 H9B 107.6
C15 C10 C11 118.5(4)
C15 C10 C9 123.4(3)
C11 C10 C9 118.1(4)
C10 C11 C12 120.0(5)
C10 C11 H11A 120.0
C12 C11 H11A 120.0
C13 C12 C11 121.3(5)
C13 C12 H12A 119.3
C11 C12 H12A 119.3
C12 C13 C14 119.3(5)
C12 C13 H13A 120.4
C14 C13 H13A 120.4
C13 C14 C15 119.5(6)
C13 C14 H14A 120.3
C15 C14 H14A 120.3
C10 C15 C14 121.3(4)
C10 C15 H15A 119.3
C14 C15 H15A 119.3
C5 C16 H16B 109.5
C5 C16 H16A 109.5
H16B C16 H16A 109.5
C5 C16 H16C 109.5
H16B C16 H16C 109.5
H16A C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.667(3)
N1 C1 1.342(4)
N1 C8 1.382(4)
N1 H1A 0.8600
N2 C1 1.381(3)
N2 C2 1.405(4)
N2 C9 1.472(4)
O1 C2 1.212(3)
C2 C3 1.458(4)
C3 C4 1.388(5)
C3 C8 1.396(4)
C4 C5 1.381(5)
C4 H4A 0.9300
C5 C6 1.406(5)
C5 C16 1.501(5)
C6 C7 1.359(5)
C6 H6A 0.9300
C7 C8 1.385(4)
C7 H7A 0.9300
C9 C10 1.500(5)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.369(5)
C10 C11 1.381(5)
C11 C12 1.382(7)
C11 H11A 0.9300
C12 C13 1.357(9)
C12 H12A 0.9300
C13 C14 1.377(8)
C13 H13A 0.9300
C14 C15 1.390(6)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16B 0.9600
C16 H16A 0.9600
C16 H16C 0.9600
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
_geom_hbond_publ_flag
N1 H1A S1 7_555 0.86 2.50 3.335(3) 165 yes
C4 H4A O1 5_575 0.93 2.41 3.295(4) 159 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
C8 N1 C1 N2 -0.9(5)
C8 N1 C1 S1 179.7(3)
C2 N2 C1 N1 -4.2(5)
C9 N2 C1 N1 176.0(3)
C2 N2 C1 S1 175.1(2)
C9 N2 C1 S1 -4.6(4)
C1 N2 C2 O1 -173.6(3)
C9 N2 C2 O1 6.1(5)
C1 N2 C2 C3 6.2(5)
C9 N2 C2 C3 -174.1(3)
O1 C2 C3 C4 -4.2(5)
N2 C2 C3 C4 176.0(3)
O1 C2 C3 C8 176.6(3)
N2 C2 C3 C8 -3.1(5)
C8 C3 C4 C5 0.5(5)
C2 C3 C4 C5 -178.6(3)
C3 C4 C5 C6 -1.4(5)
C3 C4 C5 C16 177.6(3)
C4 C5 C6 C7 0.5(6)
C16 C5 C6 C7 -178.5(4)
C5 C6 C7 C8 1.3(6)
C1 N1 C8 C7 -178.2(3)
C1 N1 C8 C3 3.6(5)
C6 C7 C8 N1 179.7(4)
C6 C7 C8 C3 -2.1(6)
C4 C3 C8 N1 179.5(3)
C2 C3 C8 N1 -1.3(5)
C4 C3 C8 C7 1.3(5)
C2 C3 C8 C7 -179.6(3)
C1 N2 C9 C10 97.0(3)
C2 N2 C9 C10 -82.7(3)
N2 C9 C10 C15 -13.4(5)
N2 C9 C10 C11 167.7(3)
C15 C10 C11 C12 0.3(6)
C9 C10 C11 C12 179.3(4)
C10 C11 C12 C13 -2.3(8)
C11 C12 C13 C14 3.8(10)
C12 C13 C14 C15 -3.2(8)
C11 C10 C15 C14 0.2(6)
C9 C10 C15 C14 -178.7(4)
C13 C14 C15 C10 1.3(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19588216
