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#$Date: 2023-05-22 10:10:18 +0300 (Mon, 22 May 2023) $
#$Revision: 283916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107223.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_8107223
loop_
_publ_author_name
'El-Emam, Ali A.'
'Al-Wahaibi, Lamya H.'
'Blacque, Olivier'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure of
 4-ethyl-2-{[(4-nitrophenyl)methyl]sulfanyl}-6-oxo-1,6-dihydropyrimidine-5-carbonitrile,
 C14H12N4O3S
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              811
_journal_page_last               814
_journal_paper_doi               10.1515/ncrs-2022-0272
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H12 N4 O3 S'
_chemical_formula_sum            'C14 H12 N4 O3 S'
_chemical_formula_weight         316.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 107.945(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2777(3)
_cell_length_b                   9.4312(2)
_cell_length_c                   12.9412(2)
_cell_measurement_reflns_used    10890
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      76.1
_cell_measurement_theta_min      3.6
_cell_volume                     1425.61(5)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'ShelXL [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.457
_diffrn_reflns_theta_min         4.341
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.200
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.6043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2866
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0272_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8107223
_shelx_shelxl_version_number     2017/1
_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   0.588
_shelx_estimated_absorpt_t_max   0.810
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.90018(2) 0.88851(3) 0.44589(3) 0.02485(11) Uani 1 1 d . . . . .
O1 O 0.88985(7) 0.37185(9) 0.43821(7) 0.0259(2) Uani 1 1 d . . . . .
O2 O 0.58994(12) 1.00783(15) 0.82809(10) 0.0571(4) Uani 1 1 d . . . . .
O3 O 0.73808(13) 1.14015(17) 0.89395(10) 0.0612(4) Uani 1 1 d . . . . .
N1 N 0.59363(10) 0.25275(13) 0.32561(11) 0.0383(3) Uani 1 1 d . . . . .
N2 N 0.88179(9) 0.61296(10) 0.42934(8) 0.0211(2) Uani 1 1 d D . . . .
H2N H 0.9557(8) 0.6164(16) 0.4686(11) 0.025 Uiso 1 1 d D U . . .
N3 N 0.70988(9) 0.73915(11) 0.35590(8) 0.0242(2) Uani 1 1 d . . . . .
N4 N 0.67383(11) 1.07119(14) 0.82016(10) 0.0353(3) Uani 1 1 d . . . . .
C1 C 0.64715(11) 0.35453(14) 0.33928(11) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.70985(10) 0.48497(13) 0.35747(10) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.83199(10) 0.48011(12) 0.41035(9) 0.0212(2) Uani 1 1 d . . . . .
C4 C 0.82020(10) 0.73396(12) 0.40587(9) 0.0208(2) Uani 1 1 d . . . . .
C5 C 0.65455(11) 0.61319(13) 0.33133(10) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.52736(12) 0.62386(15) 0.27902(13) 0.0369(3) Uani 1 1 d . . . . .
H6A H 0.500585 0.543255 0.228556 0.044 Uiso 1 1 calc R U . . .
H6B H 0.509062 0.712690 0.236411 0.044 Uiso 1 1 calc R U . . .
C7 C 0.46546(13) 0.62242(18) 0.36451(17) 0.0499(5) Uani 1 1 d . . . . .
H7A H 0.383469 0.638330 0.329430 0.075 Uiso 1 1 calc R U . . .
H7B H 0.496242 0.697665 0.417729 0.075 Uiso 1 1 calc R U . . .
H7C H 0.476845 0.530330 0.401382 0.075 Uiso 1 1 calc R U . . .
C8 C 0.78959(11) 1.02412(13) 0.42600(10) 0.0247(3) Uani 1 1 d . . . . .
H8A H 0.819023 1.115372 0.407696 0.030 Uiso 1 1 calc R U . . .
H8B H 0.722190 0.996837 0.364393 0.030 Uiso 1 1 calc R U . . .
C9 C 0.75399(10) 1.04231(12) 0.52650(10) 0.0229(2) Uani 1 1 d . . . . .
C10 C 0.66152(11) 0.96726(14) 0.53959(10) 0.0268(3) Uani 1 1 d . . . . .
H10 H 0.617580 0.908086 0.482518 0.032 Uiso 1 1 calc R U . . .
C11 C 0.63263(11) 0.97772(14) 0.63494(11) 0.0278(3) Uani 1 1 d . . . . .
H11 H 0.568987 0.927480 0.643696 0.033 Uiso 1 1 calc R U . . .
C12 C 0.69928(11) 1.06341(14) 0.71671(10) 0.0266(3) Uani 1 1 d . . . . .
C13 C 0.79025(11) 1.14236(14) 0.70558(11) 0.0288(3) Uani 1 1 d . . . . .
H13 H 0.833660 1.201804 0.762731 0.035 Uiso 1 1 calc R U . . .
C14 C 0.81617(11) 1.13236(13) 0.60914(11) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.876936 1.187378 0.599095 0.032 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 0.0181 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_3
C4 S1 C8 102.55(6) . .
C4 N2 C3 122.64(10) . .
C4 N2 H2N 119.8(10) . .
C3 N2 H2N 116.8(10) . .
C4 N3 C5 116.74(10) . .
O3 N4 O2 123.53(13) . .
O3 N4 C12 118.17(12) . .
O2 N4 C12 118.30(12) . .
N1 C1 C2 177.40(15) . .
C5 C2 C1 120.98(11) . .
C5 C2 C3 120.37(11) . .
C1 C2 C3 118.54(11) . .
O1 C3 N2 121.01(11) . .
O1 C3 C2 125.84(11) . .
N2 C3 C2 113.15(10) . .
N3 C4 N2 124.38(11) . .
N3 C4 S1 121.15(9) . .
N2 C4 S1 114.46(9) . .
N3 C5 C2 122.54(11) . .
N3 C5 C6 115.02(11) . .
C2 C5 C6 122.35(11) . .
C5 C6 C7 110.74(13) . .
C5 C6 H6A 109.5 . .
C7 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C7 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 S1 111.09(8) . .
C9 C8 H8A 109.4 . .
S1 C8 H8A 109.4 . .
C9 C8 H8B 109.4 . .
S1 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C10 C9 C14 119.39(11) . .
C10 C9 C8 120.83(11) . .
C14 C9 C8 119.76(11) . .
C11 C10 C9 120.89(12) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C12 C11 C10 117.97(12) . .
C12 C11 H11 121.0 . .
C10 C11 H11 121.0 . .
C11 C12 C13 122.73(12) . .
C11 C12 N4 119.05(12) . .
C13 C12 N4 118.21(12) . .
C14 C13 C12 118.29(12) . .
C14 C13 H13 120.9 . .
C12 C13 H13 120.9 . .
C13 C14 C9 120.65(12) . .
C13 C14 H14 119.7 . .
C9 C14 H14 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.7447(12) .
S1 C8 1.8249(12) .
O1 C3 1.2326(15) .
O2 N4 1.2222(17) .
O3 N4 1.2218(18) .
N1 C1 1.1458(18) .
N2 C4 1.3509(15) .
N2 C3 1.3826(15) .
N2 H2N 0.894(9) .
N3 C4 1.3097(16) .
N3 C5 1.3567(16) .
N4 C12 1.4674(16) .
C1 C2 1.4318(17) .
C2 C5 1.3771(17) .
C2 C3 1.4445(16) .
C5 C6 1.5018(18) .
C6 C7 1.523(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.5041(16) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.3918(17) .
C9 C14 1.3946(18) .
C10 C11 1.3885(18) .
C10 H10 0.9500 .
C11 C12 1.3816(19) .
C11 H11 0.9500 .
C12 C13 1.3862(19) .
C13 C14 1.3830(19) .
C13 H13 0.9500 .
C14 H14 0.9500 .
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
C4 N2 C3 O1 -175.94(11) . . . .
C4 N2 C3 C2 3.52(16) . . . .
C5 C2 C3 O1 179.29(12) . . . .
C1 C2 C3 O1 3.16(19) . . . .
C5 C2 C3 N2 -0.13(17) . . . .
C1 C2 C3 N2 -176.26(11) . . . .
C5 N3 C4 N2 3.20(18) . . . .
C5 N3 C4 S1 -177.85(9) . . . .
C3 N2 C4 N3 -5.42(18) . . . .
C3 N2 C4 S1 175.57(9) . . . .
C8 S1 C4 N3 11.16(11) . . . .
C8 S1 C4 N2 -169.79(9) . . . .
C4 N3 C5 C2 0.38(19) . . . .
C4 N3 C5 C6 177.15(12) . . . .
C1 C2 C5 N3 174.21(12) . . . .
C3 C2 C5 N3 -1.8(2) . . . .
C1 C2 C5 C6 -2.3(2) . . . .
C3 C2 C5 C6 -178.35(12) . . . .
N3 C5 C6 C7 -90.92(14) . . . .
C2 C5 C6 C7 85.85(16) . . . .
C4 S1 C8 C9 89.17(9) . . . .
S1 C8 C9 C10 -92.96(12) . . . .
S1 C8 C9 C14 85.21(12) . . . .
C14 C9 C10 C11 -1.92(19) . . . .
C8 C9 C10 C11 176.26(11) . . . .
C9 C10 C11 C12 -0.77(19) . . . .
C10 C11 C12 C13 2.39(19) . . . .
C10 C11 C12 N4 -177.21(11) . . . .
O3 N4 C12 C11 175.33(14) . . . .
O2 N4 C12 C11 -4.3(2) . . . .
O3 N4 C12 C13 -4.3(2) . . . .
O2 N4 C12 C13 176.08(14) . . . .
C11 C12 C13 C14 -1.2(2) . . . .
N4 C12 C13 C14 178.38(12) . . . .
C12 C13 C14 C9 -1.59(19) . . . .
C10 C9 C14 C13 3.13(19) . . . .
C8 C9 C14 C13 -175.07(11) . . . .
