#------------------------------------------------------------------------------
#$Date: 2020-10-07 06:50:42 +0200 (Wed 07 de Oct de 2020) $
#$Revision: 258222 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/13/7241372.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_7241372
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            'C13 H11 N3 O S'
_chemical_formula_weight         257.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                94.308(2)
_cell_angle_beta                 93.766(2)
_cell_angle_gamma                100.924(3)
_cell_formula_units_Z            2
_cell_length_a                   4.6908(2)
_cell_length_b                   9.2376(3)
_cell_length_c                   14.6613(3)
_cell_measurement_reflns_used    7574
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.7
_cell_measurement_theta_min      3.0
_cell_volume                     619.95(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_min         3.033
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.848
_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            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0327
_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)+(0.0485P)²+0.1743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2219
_reflns_number_total             2524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra07215j2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7241372
_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   0.759
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 -0.07309(8) 0.14886(4) 0.90110(2) 0.03368(13) Uani 1 1 d . . . . .
O6 O 0.7377(2) 0.56822(12) 0.92095(7) 0.0377(3) Uani 1 1 d . . . . .
N3 N 0.2302(3) 0.22848(13) 0.75839(8) 0.0275(3) Uani 1 1 d . . . . .
N2 N 1.0506(4) 0.6220(2) 0.72002(10) 0.0665(6) Uani 1 1 d . . . . .
N1 N 0.3520(3) 0.37484(13) 0.89931(8) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.316(4) 0.392(2) 0.9587(16) 0.057(6) Uiso 1 1 d . . . . .
C2 C 0.1928(3) 0.25870(15) 0.84511(10) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.5843(3) 0.46832(15) 0.86887(9) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.6264(3) 0.43784(15) 0.77324(9) 0.0277(3) Uani 1 1 d . . . . .
C4 C 0.4474(3) 0.32038(15) 0.72078(9) 0.0254(3) Uani 1 1 d . . . . .
C7 C -0.2329(3) 0.00253(17) 0.81269(11) 0.0360(3) Uani 1 1 d . . . . .
H71 H -0.330130 0.043534 0.761410 0.043 Uiso 1 1 calc R U . . .
H72 H -0.080550 -0.046990 0.788338 0.043 Uiso 1 1 calc R U . . .
C8 C -0.4520(4) -0.1060(2) 0.85724(13) 0.0495(4) Uani 1 1 d . . . . .
H81 H -0.552643 -0.184146 0.810913 0.074 Uiso 1 1 calc R U . . .
H82 H -0.594290 -0.054168 0.884340 0.074 Uiso 1 1 calc R U . . .
H83 H -0.351000 -0.150108 0.905368 0.074 Uiso 1 1 calc R U . . .
C9 C 0.8597(4) 0.53841(18) 0.74085(10) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.4687(3) 0.28429(15) 0.62158(9) 0.0257(3) Uani 1 1 d . . . . .
C11A C 0.7349(6) 0.3195(3) 0.58165(19) 0.0288(7) Uani 0.501(3) 1 d . . P A 1
H111 H 0.907480 0.362822 0.619089 0.035 Uiso 0.501(3) 1 calc R U P A 1
C11B C 0.5757(6) 0.3944(3) 0.56483(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2
H112 H 0.638403 0.494030 0.590053 0.036 Uiso 0.499(3) 1 calc R U P A 2
C12A C 0.7465(6) 0.2912(3) 0.48760(19) 0.0299(7) Uani 0.501(3) 1 d . . P A 1
H121 H 0.924366 0.319802 0.460270 0.036 Uiso 0.501(3) 1 calc R U P A 1
C12B C 0.5900(7) 0.3581(3) 0.4721(2) 0.0330(7) Uani 0.499(3) 1 d . . P A 2
H122 H 0.669271 0.433239 0.434938 0.040 Uiso 0.499(3) 1 calc R U P A 2
C13 C 0.4954(3) 0.22053(17) 0.43356(10) 0.0318(3) Uani 1 1 d . . . . .
H131 H 0.505377 0.195620 0.369949 0.038 Uiso 0.501(3) 1 calc R U P A 1
H132 H 0.501799 0.198819 0.369442 0.038 Uiso 0.499(3) 1 calc R U P A 2
C14A C 0.2349(7) 0.1869(3) 0.4717(2) 0.0328(7) Uani 0.501(3) 1 d . . P A 1
H141 H 0.062719 0.144981 0.433782 0.039 Uiso 0.501(3) 1 calc R U P A 1
C14B C 0.3835(6) 0.1050(3) 0.49002(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2
H142 H 0.321559 0.005754 0.463919 0.036 Uiso 0.499(3) 1 calc R U P A 2
C15A C 0.2212(6) 0.2139(3) 0.56574(19) 0.0301(7) Uani 0.501(3) 1 d . . P A 1
H151 H 0.042145 0.184157 0.592197 0.036 Uiso 0.501(3) 1 calc R U P A 1
C15B C 0.3672(6) 0.1403(3) 0.58279(19) 0.0277(7) Uani 0.499(3) 1 d . . P A 2
H152 H 0.286210 0.065741 0.620075 0.033 Uiso 0.499(3) 1 calc R U P A 2
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 102.73(7) . . ?
C2 N3 C4 117.49(12) . . ?
C2 N1 C6 122.14(12) . . ?
C2 N1 H1 121.4(14) . . ?
C6 N1 H1 116.4(14) . . ?
N3 C2 N1 124.39(13) . . ?
N3 C2 S1 121.82(11) . . ?
N1 C2 S1 113.79(10) . . ?
O6 C6 N1 121.16(12) . . ?
O6 C6 C5 124.75(13) . . ?
N1 C6 C5 114.09(12) . . ?
C4 C5 C9 125.41(13) . . ?
C4 C5 C6 120.55(12) . . ?
C9 C5 C6 114.04(12) . . ?
N3 C4 C5 121.17(12) . . ?
N3 C4 C10 114.71(12) . . ?
C5 C4 C10 124.11(12) . . ?
C8 C7 S1 106.66(11) . . ?
C8 C7 H71 110.4 . . ?
S1 C7 H71 110.4 . . ?
C8 C7 H72 110.4 . . ?
S1 C7 H72 110.4 . . ?
H71 C7 H72 108.6 . . ?
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 176.09(16) . . ?
C15B C10 C11B 119.08(19) . . ?
C15A C10 C11A 118.68(19) . . ?
C15B C10 C4 119.60(15) . . ?
C15A C10 C4 119.96(16) . . ?
C11B C10 C4 121.23(16) . . ?
C11A C10 C4 121.36(16) . . ?
C12A C11A C10 120.3(2) . . ?
C12A C11A H111 119.9 . . ?
C10 C11A H111 119.9 . . ?
C12B C11B C10 120.1(2) . . ?
C12B C11B H112 119.9 . . ?
C10 C11B H112 119.9 . . ?
C11A C12A C13 119.6(2) . . ?
C11A C12A H121 120.2 . . ?
C13 C12A H121 120.2 . . ?
C13 C12B C11B 121.8(3) . . ?
C13 C12B H122 119.1 . . ?
C11B C12B H122 119.1 . . ?
C14A C13 C12A 120.4(2) . . ?
C12B C13 C14B 119.43(19) . . ?
C14A C13 H131 119.8 . . ?
C12A C13 H131 119.8 . . ?
C12B C13 H132 120.3 . . ?
C14B C13 H132 120.3 . . ?
C13 C14A C15A 120.3(3) . . ?
C13 C14A H141 119.8 . . ?
C15A C14A H141 119.8 . . ?
C15B C14B C13 119.2(2) . . ?
C15B C14B H142 120.4 . . ?
C13 C14B H142 120.4 . . ?
C14A C15A C10 120.5(2) . . ?
C14A C15A H151 119.8 . . ?
C10 C15A H151 119.8 . . ?
C14B C15B C10 120.3(2) . . ?
C14B C15B H152 119.8 . . ?
C10 C15B H152 119.8 . . ?
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 1.7432(14) . ?
S1 C7 1.8150(15) . ?
O6 C6 1.2339(17) . ?
N3 C2 1.3113(18) . ?
N3 C4 1.3707(18) . ?
N2 C9 1.141(2) . ?
N1 C2 1.3531(18) . ?
N1 C6 1.3775(18) . ?
N1 H1 0.91(2) . ?
C6 C5 1.4429(19) . ?
C5 C4 1.385(2) . ?
C5 C9 1.427(2) . ?
C4 C10 1.4817(19) . ?
C7 C8 1.511(2) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C10 C15B 1.389(3) . ?
C10 C15A 1.397(3) . ?
C10 C11B 1.402(3) . ?
C10 C11A 1.407(3) . ?
C11A C12A 1.391(4) . ?
C11A H111 0.9500 . ?
C11B C12B 1.385(4) . ?
C11B H112 0.9500 . ?
C12A C13 1.396(3) . ?
C12A H121 0.9500 . ?
C12B C13 1.333(3) . ?
C12B H122 0.9500 . ?
C13 C14A 1.369(3) . ?
C13 C14B 1.442(3) . ?
C13 H131 0.9500 . ?
C13 H132 0.9500 . ?
C14A C15A 1.390(4) . ?
C14A H141 0.9500 . ?
C14B C15B 1.385(4) . ?
C14B H142 0.9500 . ?
C15A H151 0.9500 . ?
C15B H152 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 0.6(2) . . . . ?
C4 N3 C2 S1 -179.20(10) . . . . ?
C6 N1 C2 N3 -4.1(2) . . . . ?
C6 N1 C2 S1 175.68(11) . . . . ?
C7 S1 C2 N3 2.07(14) . . . . ?
C7 S1 C2 N1 -177.77(11) . . . . ?
C2 N1 C6 O6 -175.59(14) . . . . ?
C2 N1 C6 C5 4.5(2) . . . . ?
O6 C6 C5 C4 178.21(14) . . . . ?
N1 C6 C5 C4 -1.9(2) . . . . ?
O6 C6 C5 C9 -2.3(2) . . . . ?
N1 C6 C5 C9 177.60(13) . . . . ?
C2 N3 C4 C5 2.1(2) . . . . ?
C2 N3 C4 C10 -177.19(12) . . . . ?
C9 C5 C4 N3 179.26(14) . . . . ?
C6 C5 C4 N3 -1.3(2) . . . . ?
C9 C5 C4 C10 -1.6(2) . . . . ?
C6 C5 C4 C10 177.83(13) . . . . ?
C2 S1 C7 C8 175.62(12) . . . . ?
N3 C4 C10 C15B -25.4(2) . . . . ?
C5 C4 C10 C15B 155.37(18) . . . . ?
N3 C4 C10 C15A 27.8(2) . . . . ?
C5 C4 C10 C15A -151.43(19) . . . . ?
N3 C4 C10 C11B 151.21(18) . . . . ?
C5 C4 C10 C11B -28.0(2) . . . . ?
N3 C4 C10 C11A -152.21(18) . . . . ?
C5 C4 C10 C11A 28.6(2) . . . . ?
C15A C10 C11A C12A 3.2(3) . . . . ?
C4 C10 C11A C12A -176.8(2) . . . . ?
C15B C10 C11B C12B -2.5(4) . . . . ?
C4 C10 C11B C12B -179.2(2) . . . . ?
C10 C11A C12A C13 -3.3(4) . . . . ?
C10 C11B C12B C13 2.2(4) . . . . ?
C11B C12B C13 C14B -2.0(4) . . . . ?
C11A C12A C13 C14A 3.8(4) . . . . ?
C12A C13 C14A C15A -4.3(4) . . . . ?
C12B C13 C14B C15B 2.2(4) . . . . ?
C13 C14A C15A C10 4.2(4) . . . . ?
C11A C10 C15A C14A -3.6(4) . . . . ?
C4 C10 C15A C14A 176.4(2) . . . . ?
C13 C14B C15B C10 -2.6(4) . . . . ?
C11B C10 C15B C14B 2.8(4) . . . . ?
C4 C10 C15B C14B 179.5(2) . . . . ?
