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#$Date: 2020-10-07 07:50:42 +0300 (Wed, 07 Oct 2020) $
#$Revision: 258222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241371.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_7241371
loop_
_publ_author_name
'Al-Wahaibi, Lamya H.'
'Chakraborty, Kushumita'
'Al-Shaalan, Nora H.'
'Syed Majeed, Mohamed Yehya Annavi'
'Blacque, Olivier'
'Al-Mutairi, Aamal A.'
'El-Emam, Ali A.'
'Percino, M. Judith'
'Thamotharan, Subbiah'
_publ_section_title
;
 Quantitative analysis of hydrogen and chalcogen bonds in two
 pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: an
 integrated crystallographic and theoretical study
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              36806
_journal_page_last               36817
_journal_paper_doi               10.1039/D0RA07215J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C11 H9 N3 O S2'
_chemical_formula_weight         263.33
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.268(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5546(2)
_cell_length_b                   4.9907(5)
_cell_length_c                   17.1813(3)
_cell_measurement_reflns_used    7920
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.0
_cell_measurement_theta_min      3.4
_cell_volume                     1146.50(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11447
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.466
_diffrn_reflns_theta_min         3.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.102
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0249
_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)+(0.0358P)²+0.4259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2147
_reflns_number_total             2336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra07215j2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241371
_shelx_shelxl_version_number     2018/3
_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   0.709
_shelx_estimated_absorpt_t_max   0.887
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 0.42521(2) 0.59528(7) 0.34017(2) 0.02616(11) Uani 1 1 d . . . . .
S2 S 0.76320(2) 0.74865(6) 0.32497(2) 0.02129(10) Uani 1 1 d . . . . .
O6 O 0.62778(7) -0.0907(2) 0.53533(6) 0.0268(2) Uani 1 1 d . . . . .
N3 N 0.61745(8) 0.5081(2) 0.37174(7) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.87904(10) -0.0633(3) 0.56368(8) 0.0339(3) Uani 1 1 d . . . . .
N1 N 0.54303(9) 0.2397(2) 0.44340(8) 0.0226(2) Uani 1 1 d . . . . .
H1 H 0.4878(16) 0.195(4) 0.4500(13) 0.043(5) Uiso 1 1 d . . . . .
C2 C 0.54074(10) 0.4376(3) 0.38833(8) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.62894(10) 0.0950(3) 0.48798(8) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.71540(9) 0.1793(3) 0.47324(8) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.70668(9) 0.3793(3) 0.41452(8) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.44546(10) 0.8079(3) 0.26273(9) 0.0258(3) Uani 1 1 d . . . . .
H71 H 0.498770 0.940227 0.291544 0.031 Uiso 1 1 calc R U . . .
H72 H 0.466061 0.698405 0.224329 0.031 Uiso 1 1 calc R U . . .
C8 C 0.34727(12) 0.9505(3) 0.21272(10) 0.0352(4) Uani 1 1 d . . . . .
H81 H 0.324724 1.045665 0.251883 0.053 Uiso 1 1 calc R U . . .
H82 H 0.296669 0.818608 0.180453 0.053 Uiso 1 1 calc R U . . .
H83 H 0.357198 1.079059 0.173626 0.053 Uiso 1 1 calc R U . . .
C9 C 0.80637(10) 0.0445(3) 0.52234(9) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.78716(9) 0.4741(3) 0.39190(8) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.88466(10) 0.3844(3) 0.41504(8) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.912243 0.235258 0.451109 0.025 Uiso 1 1 calc R U . . .
C12 C 0.93798(10) 0.5417(3) 0.37841(9) 0.0236(3) Uani 1 1 d . . . . .
H12 H 1.005713 0.509391 0.387277 0.028 Uiso 1 1 calc R U . . .
C13 C 0.88233(10) 0.7440(3) 0.32922(9) 0.0241(3) Uani 1 1 d . . . . .
H13 H 0.907012 0.868893 0.300427 0.029 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
_geom_angle_publ_flag
C2 S1 C7 101.93(6) . . ?
C13 S2 C10 91.50(6) . . ?
C2 N3 C4 117.83(11) . . ?
C2 N1 C6 122.20(12) . . ?
C2 N1 H1 120.0(14) . . ?
C6 N1 H1 117.7(14) . . ?
N3 C2 N1 124.07(12) . . ?
N3 C2 S1 121.56(10) . . ?
N1 C2 S1 114.37(10) . . ?
O6 C6 N1 120.71(12) . . ?
O6 C6 C5 125.02(12) . . ?
N1 C6 C5 114.27(11) . . ?
C4 C5 C9 124.46(12) . . ?
C4 C5 C6 120.13(12) . . ?
C9 C5 C6 115.41(12) . . ?
N3 C4 C5 121.39(12) . . ?
N3 C4 C10 113.36(11) . . ?
C5 C4 C10 125.25(12) . . ?
C8 C7 S1 107.41(10) . . ?
C8 C7 H71 110.2 . . ?
S1 C7 H71 110.2 . . ?
C8 C7 H72 110.2 . . ?
S1 C7 H72 110.2 . . ?
H71 C7 H72 108.5 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N2 C9 C5 178.24(15) . . ?
C11 C10 C4 131.28(12) . . ?
C11 C10 S2 111.11(10) . . ?
C4 C10 S2 117.61(9) . . ?
C10 C11 C12 111.83(12) . . ?
C10 C11 H11 124.1 . . ?
C12 C11 H11 124.1 . . ?
C13 C12 C11 113.08(12) . . ?
C13 C12 H12 123.5 . . ?
C11 C12 H12 123.5 . . ?
C12 C13 S2 112.48(10) . . ?
C12 C13 H13 123.8 . . ?
S2 C13 H13 123.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7412(13) . ?
S1 C7 1.8143(14) . ?
S2 C13 1.7065(14) . ?
S2 C10 1.7331(13) . ?
O6 C6 1.2376(17) . ?
N3 C2 1.3049(17) . ?
N3 C4 1.3733(17) . ?
N2 C9 1.1484(19) . ?
N1 C2 1.3590(18) . ?
N1 C6 1.3839(18) . ?
N1 H1 0.88(2) . ?
C6 C5 1.4411(18) . ?
C5 C4 1.3887(19) . ?
C5 C9 1.4266(19) . ?
C4 C10 1.4515(17) . ?
C7 C8 1.522(2) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C10 C11 1.3882(18) . ?
C11 C12 1.4144(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.360(2) . ?
C12 H12 0.9500 . ?
C13 H13 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
_geom_torsion_publ_flag
C4 N3 C2 N1 -1.99(19) . . . . ?
C4 N3 C2 S1 177.95(9) . . . . ?
C6 N1 C2 N3 0.6(2) . . . . ?
C6 N1 C2 S1 -179.34(10) . . . . ?
C7 S1 C2 N3 7.47(13) . . . . ?
C7 S1 C2 N1 -172.58(10) . . . . ?
C2 N1 C6 O6 -177.32(13) . . . . ?
C2 N1 C6 C5 2.23(19) . . . . ?
O6 C6 C5 C4 175.84(13) . . . . ?
N1 C6 C5 C4 -3.68(18) . . . . ?
O6 C6 C5 C9 -4.2(2) . . . . ?
N1 C6 C5 C9 176.31(12) . . . . ?
C2 N3 C4 C5 0.36(18) . . . . ?
C2 N3 C4 C10 -179.52(11) . . . . ?
C9 C5 C4 N3 -177.45(12) . . . . ?
C6 C5 C4 N3 2.55(19) . . . . ?
C9 C5 C4 C10 2.4(2) . . . . ?
C6 C5 C4 C10 -177.59(12) . . . . ?
C2 S1 C7 C8 177.57(11) . . . . ?
N3 C4 C10 C11 -174.27(13) . . . . ?
C5 C4 C10 C11 5.9(2) . . . . ?
N3 C4 C10 S2 6.23(15) . . . . ?
C5 C4 C10 S2 -173.64(10) . . . . ?
C13 S2 C10 C11 -0.62(10) . . . . ?
C13 S2 C10 C4 178.97(10) . . . . ?
C4 C10 C11 C12 -179.08(13) . . . . ?
S2 C10 C11 C12 0.45(14) . . . . ?
C10 C11 C12 C13 0.04(17) . . . . ?
C11 C12 C13 S2 -0.52(16) . . . . ?
C10 S2 C13 C12 0.65(11) . . . . ?
