#------------------------------------------------------------------------------
#$Date: 2021-04-24 08:01:14 +0300 (Sat, 24 Apr 2021) $
#$Revision: 264500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243813.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_2243813
loop_
_publ_author_name
'Mohamed-Ezzat, Reham A.'
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structures of
 (E)-2-amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile
 and
 (E)-2-amino-4-methylsulfanyl-6-oxo-1-[1-(pyridin-2-yl)ethylideneamino]-1,6-dihydropyrimidine-5-carbonitrile
;
_journal_coeditor_code           JY2007
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              547
_journal_page_last               550
_journal_paper_doi               10.1107/S2056989021004126
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H13 N5 O S'
_chemical_formula_moiety         'C14 H13 N5 O S'
_chemical_formula_sum            'C14 H13 N5 O S'
_chemical_formula_weight         299.35
_chemical_name_systematic
(E)-2-Amino-4-methylsulfanyl-6-oxo-1-(1-phenylethylideneamino)-1,6-dihydropyrimidine-5-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.7607(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.15369(18)
_cell_length_b                   14.9466(2)
_cell_length_c                   7.68691(16)
_cell_measurement_reflns_used    58984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0950
_cell_measurement_theta_min      3.6310
_cell_volume                     1395.72(4)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            104992
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.738
_diffrn_reflns_theta_min         3.638
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0395
_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)+(0.0516P)²+0.8822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2842
_reflns_number_total             2958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2007sup1.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243813
_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   0.676
_shelx_estimated_absorpt_t_max   0.959
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.47431(10) 0.36271(8) 0.24782(18) 0.0248(3) Uani d 1 . .
N N2 0.37697(11) 0.37729(8) 0.34251(18) 0.0264(3) Uani d 1 . .
C C2 0.53906(13) 0.43583(10) 0.2177(2) 0.0253(3) Uani d 1 . .
N N6 0.50093(13) 0.51489(9) 0.2657(2) 0.0299(3) Uani d 1 . .
H H061 0.5387(18) 0.5609(17) 0.251(3) 0.043(6) Uiso d 1 . .
H H062 0.441(2) 0.5174(16) 0.319(3) 0.050(7) Uiso d 1 . .
N N3 0.63513(11) 0.43021(8) 0.13939(17) 0.0252(3) Uani d 1 . .
C C4 0.67045(12) 0.34825(10) 0.1009(2) 0.0240(3) Uani d 1 . .
S S1 0.79679(3) 0.33529(3) -0.00002(6) 0.03105(14) Uani d 1 . .
C C5 0.61368(12) 0.26976(9) 0.1394(2) 0.0238(3) Uani d 1 . .
C C6 0.50952(13) 0.27387(9) 0.2196(2) 0.0241(3) Uani d 1 . .
O O1 0.45193(9) 0.21063(7) 0.26161(15) 0.0286(3) Uani d 1 . .
C C7 0.28666(13) 0.35750(9) 0.2578(2) 0.0260(3) Uani d 1 . .
C C8 0.27945(15) 0.32587(13) 0.0737(2) 0.0376(4) Uani d 1 . .
H H8A 0.343475 0.347475 0.011570 0.056 Uiso calc 1 . .
H H8B 0.211966 0.349048 0.017032 0.056 Uiso calc 1 . .
H H8C 0.278191 0.260323 0.071499 0.056 Uiso calc 1 . .
C C9 0.18442(13) 0.36712(10) 0.3563(2) 0.0275(3) Uani d 1 . .
C C10 0.08665(16) 0.33019(13) 0.2925(3) 0.0387(4) Uani d 1 . .
H H10 0.084914 0.300421 0.183268 0.046 Uiso calc 1 . .
C C11 -0.00923(16) 0.33629(15) 0.3871(3) 0.0472(5) Uani d 1 . .
H H11 -0.075770 0.310997 0.341450 0.057 Uiso calc 1 . .
C C12 -0.00802(16) 0.37845(15) 0.5449(3) 0.0459(5) Uani d 1 . .
H H12 -0.073084 0.381751 0.610018 0.055 Uiso calc 1 . .
C C13 0.08929(16) 0.41639(15) 0.6092(3) 0.0458(5) Uani d 1 . .
H H13 0.090130 0.446323 0.718242 0.055 Uiso calc 1 . .
C C14 0.18491(15) 0.41128(12) 0.5170(2) 0.0351(4) Uani d 1 . .
H H14 0.250819 0.437667 0.562552 0.042 Uiso calc 1 . .
N N4 0.68678(12) 0.11352(9) 0.0616(2) 0.0315(3) Uani d 1 . .
C C15 0.65497(12) 0.18367(10) 0.0965(2) 0.0256(3) Uani d 1 . .
C C16 0.83220(16) 0.44877(12) -0.0485(3) 0.0419(4) Uani d 1 . .
H H16A 0.792700 0.467742 -0.155236 0.063 Uiso calc 1 . .
H H16B 0.911681 0.453120 -0.064728 0.063 Uiso calc 1 . .
H H16C 0.811591 0.487512 0.048102 0.063 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 0.0181 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . 123.03(13) ?
C2 N1 N2 . . 117.02(12) ?
C6 N1 N2 . . 118.81(11) ?
C7 N2 N1 . . 114.40(13) y
N6 C2 N3 . . 120.02(14) ?
N6 C2 N1 . . 117.16(14) ?
N3 C2 N1 . . 122.79(13) ?
C2 N3 C4 . . 116.77(13) ?
N3 C4 C5 . . 124.02(14) y
N3 C4 S1 . . 119.47(11) ?
C5 C4 S1 . . 116.49(11) ?
C4 S1 C16 . . 101.93(8) y
C4 C5 C15 . . 122.01(14) ?
C4 C5 C6 . . 120.40(13) ?
C15 C5 C6 . . 117.57(13) ?
O1 C6 N1 . . 120.40(13) ?
O1 C6 C5 . . 127.05(13) ?
N1 C6 C5 . . 112.55(12) y
N2 C7 C9 . . 115.63(14) ?
N2 C7 C8 . . 125.04(15) ?
C9 C7 C8 . . 119.32(15) ?
C10 C9 C14 . . 118.69(16) ?
C10 C9 C7 . . 120.25(16) ?
C14 C9 C7 . . 121.04(15) ?
C9 C10 C11 . . 120.68(19) ?
C12 C11 C10 . . 120.41(18) ?
C11 C12 C13 . . 119.33(18) ?
C14 C13 C12 . . 121.04(19) ?
C13 C14 C9 . . 119.84(17) ?
N4 C15 C5 . . 178.96(16) ?
C2 N6 H061 . . 120.0(16) ?
C2 N6 H062 . . 119.2(17) ?
H061 N6 H062 . . 121(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 H14 . . 120.1 ?
C9 C14 H14 . . 120.1 ?
S1 C16 H16A . . 109.5 ?
S1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3705(19) ?
N1 C6 . 1.4138(18) ?
N1 N2 . 1.4248(17) y
N2 C7 . 1.293(2) ?
C2 N6 . 1.326(2) ?
C2 N3 . 1.333(2) y
N3 C4 . 1.3343(19) ?
C4 C5 . 1.397(2) ?
C4 S1 . 1.7522(16) y
S1 C16 . 1.7918(19) y
C5 C15 . 1.424(2) ?
C5 C6 . 1.427(2) ?
C6 O1 . 1.2253(18) ?
C7 C9 . 1.482(2) ?
C7 C8 . 1.492(2) ?
C9 C10 . 1.386(2) ?
C9 C14 . 1.401(2) ?
C10 C11 . 1.395(3) ?
C11 C12 . 1.367(3) ?
C12 C13 . 1.389(3) ?
C13 C14 . 1.382(3) ?
N4 C15 . 1.152(2) ?
N6 H061 . 0.84(2) ?
N6 H062 . 0.84(2) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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
N6 H061 O1 2_655 0.84(2) 2.24(3) 2.9899(17) 149(2) yes
N6 H062 N4 2_655 0.84(2) 2.33(2) 3.054(2) 144(2) yes
C8 H8A O1 4_565 0.98 2.52 3.279(2) 134.4 yes
N6 H062 N2 . 0.84(2) 2.25(2) 2.6273(19) 108(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 N2 C7 . . . . 118.94(15) ?
C6 N1 N2 C7 . . . . -72.88(18) ?
C6 N1 C2 N6 . . . . -173.38(14) ?
N2 N1 C2 N6 . . . . -5.7(2) ?
C6 N1 C2 N3 . . . . 8.5(2) ?
N2 N1 C2 N3 . . . . 176.15(14) ?
N6 C2 N3 C4 . . . . 177.46(15) ?
N1 C2 N3 C4 . . . . -4.5(2) ?
C2 N3 C4 C5 . . . . -0.7(2) ?
C2 N3 C4 S1 . . . . -179.30(11) ?
N3 C4 S1 C16 . . . . -7.90(16) ?
C5 C4 S1 C16 . . . . 173.40(13) ?
N3 C4 C5 C15 . . . . -179.67(15) ?
S1 C4 C5 C15 . . . . -1.0(2) ?
N3 C4 C5 C6 . . . . 2.1(3) ?
S1 C4 C5 C6 . . . . -179.25(12) ?
C2 N1 C6 O1 . . . . 174.16(15) ?
N2 N1 C6 O1 . . . . 6.7(2) ?
C2 N1 C6 C5 . . . . -6.5(2) ?
N2 N1 C6 C5 . . . . -173.87(13) ?
C4 C5 C6 O1 . . . . -179.25(16) ?
C15 C5 C6 O1 . . . . 2.5(3) ?
C4 C5 C6 N1 . . . . 1.4(2) ?
C15 C5 C6 N1 . . . . -176.89(14) ?
N1 N2 C7 C9 . . . . 176.69(12) y
N1 N2 C7 C8 . . . . -2.8(2) ?
N2 C7 C9 C10 . . . . -166.23(15) y
C8 C7 C9 C10 . . . . 13.2(2) ?
N2 C7 C9 C14 . . . . 12.1(2) y
C8 C7 C9 C14 . . . . -168.47(16) ?
C14 C9 C10 C11 . . . . -0.5(3) ?
C7 C9 C10 C11 . . . . 177.85(16) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
C10 C11 C12 C13 . . . . 1.0(3) ?
C11 C12 C13 C14 . . . . -0.7(3) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
C10 C9 C14 C13 . . . . 0.7(3) ?
C7 C9 C14 C13 . . . . -177.59(16) ?

_cod_database_fobs_code 2243813
