#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:49:39 +0300 (Sat, 06 May 2023) $
#$Revision: 283599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244245.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_2244245
loop_
_publ_author_name
'Mohamed-Ezzat, Reham A'
'Kariuki, Benson M.'
'Azzam, Rasha A.'
_publ_section_title
;
 Synthesis and crystal structure of
 N-(5-acetyl-4-methyl-pyrimidin-2-yl)benzene-sulfonamide.
;
_journal_coeditor_code           YZ2029
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              331
_journal_page_last               334
_journal_paper_doi               10.1107/S2056989023001871
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H13 N3 O3 S'
_chemical_formula_moiety         'C13 H13 N3 O3 S'
_chemical_formula_sum            'C13 H13 N3 O3 S'
_chemical_formula_weight         291.32
_chemical_name_systematic
;
N-(5-Acetyl-4-methylpyrimidin-2-yl)benzenesulfonamide
;
_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-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 113.900(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0699(6)
_cell_length_b                   14.7429(6)
_cell_length_c                   10.5212(7)
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6630
_cell_measurement_theta_min      3.8650
_cell_volume                     1428.04(16)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020), ORTEP-3 for Windows (Farrugia,
2012)
;
_computing_publication_material
;
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type
'Rigaku SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12642
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.537
_diffrn_reflns_theta_min         3.482
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0459
_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)+(0.0493P)²+0.4200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2548
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2029sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2244245.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244245
_cod_database_fobs_code          2244245
_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   0.903
_shelx_estimated_absorpt_t_max   0.963
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
C C1 0.5229(2) 0.75192(12) 0.26887(19) 0.0461(4) Uani d 1 . .
C C2 0.6205(2) 0.76291(14) 0.2086(2) 0.0552(5) Uani d 1 . .
H H2 0.630570 0.718727 0.150041 0.066 Uiso calc 1 . .
C C3 0.7033(2) 0.84155(15) 0.2374(3) 0.0651(6) Uani d 1 . .
H H3 0.768869 0.850929 0.196825 0.078 Uiso calc 1 . .
C C4 0.6886(3) 0.90550(15) 0.3257(3) 0.0712(7) Uani d 1 . .
H H4 0.746248 0.957279 0.346473 0.085 Uiso calc 1 . .
C C5 0.5901(3) 0.89393(15) 0.3833(2) 0.0696(6) Uani d 1 . .
H H5 0.579890 0.938259 0.441639 0.083 Uiso calc 1 . .
C C6 0.5065(3) 0.81732(14) 0.3555(2) 0.0580(5) Uani d 1 . .
H H6 0.439261 0.809307 0.394462 0.070 Uiso calc 1 . .
C C7 0.6186(2) 0.52796(12) 0.37144(19) 0.0463(4) Uani d 1 . .
C C8 0.8002(2) 0.49089(16) 0.3045(2) 0.0579(5) Uani d 1 . .
C C10 0.7564(2) 0.40722(14) 0.4752(2) 0.0568(5) Uani d 1 . .
H H10 0.780068 0.359996 0.539203 0.068 Uiso calc 1 A 1
C C11 0.8767(3) 0.5141(2) 0.2123(3) 0.0835(8) Uani d 1 . .
H H11A 0.853870 0.469409 0.140165 0.125 Uiso calc 1 . .
H H11B 0.979663 0.514976 0.266457 0.125 Uiso calc 1 . .
H H11C 0.845364 0.572710 0.171410 0.125 Uiso calc 1 . .
N N1 0.50291(19) 0.58192(11) 0.35938(18) 0.0508(4) Uani d 1 . .
N N2 0.69070(18) 0.54638(11) 0.29291(17) 0.0537(4) Uani d 1 . .
N N3 0.64728(17) 0.46152(10) 0.46533(16) 0.0496(4) Uani d 1 . .
O O1 0.28821(16) 0.67414(10) 0.25840(16) 0.0653(4) Uani d 1 . .
O O2 0.39885(17) 0.61859(10) 0.10316(14) 0.0621(4) Uani d 1 . .
S S1 0.41467(5) 0.65419(3) 0.23421(5) 0.04929(17) Uani d 1 . .
C C9 0.8367(2) 0.41647(16) 0.3968(2) 0.0600(5) Uani d 0.591(11) B 1
C C12 0.9420(7) 0.3432(4) 0.3990(8) 0.0750(19) Uani d 0.591(11) B 1
C C13 0.9860(17) 0.2756(10) 0.5150(18) 0.098(4) Uani d 0.591(11) B 1
H H13A 1.053800 0.233375 0.505298 0.148 Uiso calc 0.591(11) B 1
H H13B 0.901665 0.243536 0.511702 0.148 Uiso calc 0.591(11) B 1
H H13C 1.030623 0.306600 0.602434 0.148 Uiso calc 0.591(11) B 1
O O3 0.9931(8) 0.3397(4) 0.3128(8) 0.110(2) Uani d 0.591(11) B 1
C C9A 0.8367(2) 0.41647(16) 0.3968(2) 0.0600(5) Uani d 0.409(11) B 2
C C12A 0.9727(9) 0.3620(7) 0.4306(12) 0.079(3) Uani d 0.409(11) B 2
C C13A 0.990(2) 0.2750(12) 0.509(3) 0.089(4) Uani d 0.409(11) B 2
H H13D 1.082486 0.248722 0.525215 0.133 Uiso calc 0.409(11) B 2
H H13E 0.913988 0.233796 0.454891 0.133 Uiso calc 0.409(11) B 2
H H13F 0.983594 0.286757 0.595831 0.133 Uiso calc 0.409(11) B 2
O O3A 1.0616(8) 0.3857(7) 0.3876(10) 0.106(3) Uani d 0.409(11) B 2
H H1 0.458(2) 0.5700(14) 0.409(2) 0.054(6) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 C1 C6 . . 121.33(19) ?
C2 C1 S1 . . 120.01(15) ?
C6 C1 S1 . . 118.66(15) ?
C1 C2 C3 . . 118.4(2) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C4 C3 C2 . . 120.1(2) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C5 C4 C3 . . 120.8(2) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.2(2) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.3(2) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
N2 C7 N3 . . 126.86(17) ?
N2 C7 N1 . . 118.71(17) ?
N3 C7 N1 . . 114.43(16) ?
N2 C8 C9A . . 120.86(18) ?
N2 C8 C9 . . 120.86(18) ?
N2 C8 C11 . . 114.9(2) ?
C9A C8 C11 . . 124.2(2) ?
C9 C8 C11 . . 124.2(2) ?
N3 C10 C9A . . 124.15(19) ?
N3 C10 C9 . . 124.15(19) ?
N3 C10 H10 . . 117.9 ?
C9 C10 H10 . . 117.9 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 N1 S1 . . 127.69(14) ?
C7 N1 H1 . . 118.2(14) ?
S1 N1 H1 . . 112.6(15) ?
C7 N2 C8 . . 117.10(17) ?
C10 N3 C7 . . 115.02(17) ?
O2 S1 O1 . . 119.43(10) ?
O2 S1 N1 . . 110.41(9) ?
O1 S1 N1 . . 102.84(9) ?
O2 S1 C1 . . 108.71(9) ?
O1 S1 C1 . . 108.55(9) ?
N1 S1 C1 . . 106.06(9) ?
C10 C9 C8 . . 115.92(19) ?
C10 C9 C12 . . 120.0(3) ?
C8 C9 C12 . . 123.6(3) ?
O3 C12 C13 . . 120.4(5) ?
O3 C12 C9 . . 121.9(4) ?
C13 C12 C9 . . 117.6(5) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C10 C9A C8 . . 115.92(19) ?
C10 C9A C12A . . 120.4(3) ?
C8 C9A C12A . . 122.5(3) ?
O3A C12A C13A . . 121.1(5) ?
O3A C12A C9A . . 120.1(5) ?
C13A C12A C9A . . 118.6(6) ?
C12A C13A H13D . . 109.5 ?
C12A C13A H13E . . 109.5 ?
H13D C13A H13E . . 109.5 ?
C12A C13A H13F . . 109.5 ?
H13D C13A H13F . . 109.5 ?
H13E C13A H13F . . 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
C1 C2 . 1.378(3) ?
C1 C6 . 1.382(3) ?
C1 S1 . 1.7538(19) ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N2 . 1.330(2) ?
C7 N3 . 1.337(2) ?
C7 N1 . 1.374(2) ?
C8 N2 . 1.338(3) ?
C8 C9A . 1.412(3) ?
C8 C9 . 1.412(3) ?
C8 C11 . 1.502(3) ?
C10 N3 . 1.329(2) ?
C10 C9A . 1.376(3) ?
C10 C9 . 1.376(3) ?
C10 H10 . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 S1 . 1.6465(16) ?
N1 H1 . 0.83(2) ?
O1 S1 . 1.4267(15) ?
O2 S1 . 1.4226(15) ?
C9 C12 . 1.507(4) ?
C12 O3 . 1.211(5) ?
C12 C13 . 1.497(6) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C9A C12A . 1.501(5) ?
C12A O3A . 1.207(5) ?
C12A C13A . 1.495(6) ?
C13A H13D . 0.9600 ?
C13A H13E . 0.9600 ?
C13A H13F . 0.9600 ?
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
N1 H1 N3 3_666 0.83(2) 2.06(2) 2.891(2) 179(2) yes
C6 H6 O2 4_576 0.93 2.62 3.338(3) 135.0 yes
C10 H10 O1 3_666 0.93 2.54 3.243(3) 132.8 yes
C11 H11B O3A . 0.96 2.26 2.769(7) 112.6 yes
C13A H13E O1 2_645 0.96 2.50 3.40(3) 156.2 yes
