#------------------------------------------------------------------------------
#$Date: 2018-01-26 10:38:29 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242343.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_2242343
loop_
_publ_author_name
'Toze, Flavien A. A.'
'Zaytsev, Vladimir P.'
'Chervyakova, Lala V.'
'Kvyatkovskaya, Elisaveta A.'
'Dorovatovskii, Pavel V.'
'Khrustalev, Victor N.'
_publ_section_title
;
 Crystal structure of
 3-benzyl-2-[(E)-2-(furan-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one
 and
 3-benzyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one
 from synchrotron X-ray diffraction
;
_journal_coeditor_code           LD2142
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              10
_journal_page_last               14
_journal_paper_doi               10.1107/S2056989017017479
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C21 H18 N2 O S'
_chemical_formula_moiety         'C21 H18 N2 O S'
_chemical_formula_sum            'C21 H18 N2 O S'
_chemical_formula_weight         346.43
_chemical_name_systematic
3-Benzyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.245(3)
_cell_length_b                   13.855(3)
_cell_length_c                   17.629(4)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      3.0
_cell_volume                     3479.3(13)
_computing_cell_refinement
;
iMOSFLM (Battye et al.,  2011)
;
_computing_data_collection
;
Marccd (Doyle, 2011)
;
_computing_data_reduction
;
iMOSFLM (Battye et al.,  2011)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2015)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96260
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20322
_diffrn_reflns_theta_full        35.279
_diffrn_reflns_theta_max         38.493
_diffrn_reflns_theta_min         3.130
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.723
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0497
_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)+(0.0669P)²+2.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                3024
_reflns_number_total             3594
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ld2142sup1.cif
_cod_data_source_block           II
_cod_database_code               2242343
_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   0.871
_shelx_estimated_absorpt_t_max   0.891
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_occupancy
S S1 0.02475(4) 0.39698(3) 0.79544(3) 0.02956(19) Uani d 1
O O1 0.22041(10) 0.74793(9) 0.57892(8) 0.0307(3) Uani d 1
N N1 0.25131(12) 0.45803(11) 0.55151(9) 0.0249(4) Uani d 1
H H1 0.2524(17) 0.3954(19) 0.5496(12) 0.030 Uiso d 1
C C2 0.26696(14) 0.49600(12) 0.62814(11) 0.0244(4) Uani d 1
H H2 0.3287 0.4706 0.6463 0.029 Uiso calc 1
N N3 0.27450(11) 0.60304(10) 0.62410(9) 0.0229(4) Uani d 1
C C4 0.22059(13) 0.65770(13) 0.57606(10) 0.0231(4) Uani d 1
C C4A 0.16533(14) 0.60308(12) 0.51890(10) 0.0228(4) Uani d 1
C C5 0.10052(15) 0.65191(14) 0.47233(11) 0.0276(4) Uani d 1
H H5 0.0882 0.7184 0.4810 0.033 Uiso calc 1
C C6 0.05414(17) 0.60404(15) 0.41351(12) 0.0333(5) Uani d 1
H H6 0.0103 0.6371 0.3823 0.040 Uiso calc 1
C C7 0.07389(16) 0.50578(16) 0.40152(12) 0.0336(5) Uani d 1
H H7 0.0433 0.4727 0.3613 0.040 Uiso calc 1
C C8 0.13683(15) 0.45601(14) 0.44685(11) 0.0301(5) Uani d 1
H H8 0.1487 0.3896 0.4376 0.036 Uiso calc 1
C C8A 0.18367(13) 0.50393(12) 0.50701(10) 0.0234(4) Uani d 1
C C9 0.19299(14) 0.46488(12) 0.68451(11) 0.0244(4) Uani d 1
H H9 0.1295 0.4819 0.6749 0.029 Uiso calc 1
C C10 0.21254(15) 0.41433(13) 0.74758(11) 0.0264(4) Uani d 1
H H10 0.2767 0.3995 0.7566 0.032 Uiso calc 1
C C11 0.14428(15) 0.37959(13) 0.80424(10) 0.0256(4) Uani d 1
C C12 0.16756(16) 0.32822(13) 0.87251(11) 0.0304(3) Uani d 1
H H12 0.2292 0.3110 0.8879 0.037 Uiso calc 1
C C13 0.08295(16) 0.30680(14) 0.91398(11) 0.0304(3) Uani d 1
H H13 0.0830 0.2734 0.9610 0.037 Uiso calc 1
C C14 0.00234(17) 0.33875(14) 0.87974(11) 0.0304(3) Uani d 1
H H14 -0.0588 0.3298 0.9002 0.037 Uiso calc 1
C C15 0.33187(14) 0.64888(13) 0.68295(11) 0.0265(4) Uani d 1
H H15A 0.3163 0.6195 0.7326 0.032 Uiso calc 1
H H15B 0.3156 0.7183 0.6856 0.032 Uiso calc 1
C C16 0.43773(14) 0.63919(12) 0.66925(10) 0.0224(4) Uani d 1
C C17 0.47531(15) 0.60700(13) 0.60001(11) 0.0261(4) Uani d 1
H H17 0.4345 0.5901 0.5595 0.031 Uiso calc 1
C C18 0.57301(16) 0.59978(14) 0.59048(12) 0.0313(5) Uani d 1
H H18 0.5982 0.5765 0.5441 0.038 Uiso calc 1
C C19 0.63326(16) 0.62705(15) 0.64953(13) 0.0345(5) Uani d 1
H H19 0.6993 0.6232 0.6429 0.041 Uiso calc 1
C C20 0.59602(16) 0.66002(14) 0.71824(13) 0.0330(5) Uani d 1
H H20 0.6368 0.6793 0.7581 0.040 Uiso calc 1
C C21 0.49895(15) 0.66462(13) 0.72819(11) 0.0257(4) Uani d 1
H H21 0.4741 0.6852 0.7755 0.031 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1950 0.2250 '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
C14 S1 C11 92.28(10)
C8A N1 C2 117.34(15)
C8A N1 H1 116.5(16)
C2 N1 H1 113.1(15)
N1 C2 N3 108.92(14)
N1 C2 C9 113.41(16)
N3 C2 C9 111.47(15)
N1 C2 H2 107.6
N3 C2 H2 107.6
C9 C2 H2 107.6
C4 N3 C15 120.68(15)
C4 N3 C2 122.63(15)
C15 N3 C2 115.99(15)
O1 C4 N3 121.87(17)
O1 C4 C4A 122.35(17)
N3 C4 C4A 115.74(15)
C5 C4A C8A 120.09(17)
C5 C4A C4 119.86(16)
C8A C4A C4 119.83(17)
C6 C5 C4A 120.97(18)
C6 C5 H5 119.5
C4A C5 H5 119.5
C5 C6 C7 118.5(2)
C5 C6 H6 120.8
C7 C6 H6 120.8
C8 C7 C6 121.66(19)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C8A 120.21(18)
C7 C8 H8 119.9
C8A C8 H8 119.9
N1 C8A C4A 119.13(17)
N1 C8A C8 122.14(16)
C4A C8A C8 118.60(17)
C10 C9 C2 123.27(19)
C10 C9 H9 118.4
C2 C9 H9 118.4
C9 C10 C11 126.45(19)
C9 C10 H10 116.8
C11 C10 H10 116.8
C12 C11 C10 125.22(19)
C12 C11 S1 111.83(15)
C10 C11 S1 122.94(14)
C11 C12 C13 109.51(19)
C11 C12 H12 125.2
C13 C12 H12 125.2
C14 C13 C12 114.26(18)
C14 C13 H13 122.9
C12 C13 H13 122.9
C13 C14 S1 112.11(17)
C13 C14 H14 123.9
S1 C14 H14 123.9
N3 C15 C16 113.52(15)
N3 C15 H15A 108.9
C16 C15 H15A 108.9
N3 C15 H15B 108.9
C16 C15 H15B 108.9
H15A C15 H15B 107.7
C21 C16 C17 119.12(18)
C21 C16 C15 118.25(17)
C17 C16 C15 122.63(17)
C18 C17 C16 120.24(19)
C18 C17 H17 119.9
C16 C17 H17 119.9
C19 C18 C17 119.90(19)
C19 C18 H18 120.0
C17 C18 H18 120.0
C20 C19 C18 119.9(2)
C20 C19 H19 120.0
C18 C19 H19 120.0
C21 C20 C19 120.0(2)
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C21 C16 120.79(19)
C20 C21 H21 119.6
C16 C21 H21 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C14 1.721(2)
S1 C11 1.727(2)
O1 C4 1.251(2)
N1 C8A 1.396(3)
N1 C2 1.467(2)
N1 H1 0.87(3)
C2 N3 1.489(2)
C2 C9 1.511(3)
C2 H2 1.0000
N3 C4 1.371(2)
N3 C15 1.465(2)
C4 C4A 1.486(3)
C4A C5 1.409(3)
C4A C8A 1.414(2)
C5 C6 1.397(3)
C5 H5 0.9500
C6 C7 1.406(3)
C6 H6 0.9500
C7 C8 1.385(3)
C7 H7 0.9500
C8 C8A 1.418(3)
C8 H8 0.9500
C9 C10 1.343(3)
C9 H9 0.9500
C10 C11 1.475(3)
C10 H10 0.9500
C11 C12 1.437(3)
C12 C13 1.440(3)
C12 H12 0.9500
C13 C14 1.371(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.533(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C21 1.402(3)
C16 C17 1.406(3)
C17 C18 1.405(3)
C17 H17 0.9500
C18 C19 1.401(3)
C18 H18 0.9500
C19 C20 1.399(3)
C19 H19 0.9500
C20 C21 1.395(3)
C20 H20 0.9500
C21 H21 0.9500
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
N1 H1 O1 8_655 0.87(3) 2.14(3) 2.978(2) 161(2)
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
C8A N1 C2 N3 -46.4(2)
C8A N1 C2 C9 78.4(2)
N1 C2 N3 C4 37.7(2)
C9 C2 N3 C4 -88.2(2)
N1 C2 N3 C15 -151.91(16)
C9 C2 N3 C15 82.2(2)
C15 N3 C4 O1 2.2(3)
C2 N3 C4 O1 172.24(17)
C15 N3 C4 C4A -179.85(16)
C2 N3 C4 C4A -9.9(3)
O1 C4 C4A C5 -8.7(3)
N3 C4 C4A C5 173.42(17)
O1 C4 C4A C8A 165.94(18)
N3 C4 C4A C8A -11.9(3)
C8A C4A C5 C6 -0.6(3)
C4 C4A C5 C6 174.00(18)
C4A C5 C6 C7 -0.3(3)
C5 C6 C7 C8 0.7(3)
C6 C7 C8 C8A -0.3(3)
C2 N1 C8A C4A 28.7(2)
C2 N1 C8A C8 -155.42(18)
C5 C4A C8A N1 177.06(17)
C4 C4A C8A N1 2.4(3)
C5 C4A C8A C8 1.1(3)
C4 C4A C8A C8 -173.56(17)
C7 C8 C8A N1 -176.50(18)
C7 C8 C8A C4A -0.6(3)
N1 C2 C9 C10 120.5(2)
N3 C2 C9 C10 -116.17(19)
C2 C9 C10 C11 -178.56(17)
C9 C10 C11 C12 -177.92(18)
C9 C10 C11 S1 2.0(3)
C14 S1 C11 C12 0.19(15)
C14 S1 C11 C10 -179.70(16)
C10 C11 C12 C13 179.56(17)
S1 C11 C12 C13 -0.3(2)
C11 C12 C13 C14 0.4(2)
C12 C13 C14 S1 -0.2(2)
C11 S1 C14 C13 0.02(16)
C4 N3 C15 C16 -112.23(18)
C2 N3 C15 C16 77.1(2)
N3 C15 C16 C21 -168.65(15)
N3 C15 C16 C17 12.1(2)
C21 C16 C17 C18 0.5(3)
C15 C16 C17 C18 179.79(16)
C16 C17 C18 C19 -1.6(3)
C17 C18 C19 C20 1.0(3)
C18 C19 C20 C21 0.8(3)
C19 C20 C21 C16 -1.9(3)
C17 C16 C21 C20 1.2(3)
C15 C16 C21 C20 -178.09(17)

_cod_database_fobs_code 2242343
