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#$Date: 2023-01-23 12:16:16 +0200 (Mon, 23 Jan 2023) $
#$Revision: 280530 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106554.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_8106554
loop_
_publ_author_name
'Ghorab, Mostafa M.'
'Alsaid, Mansour S.'
'Al-Dosari, Mohmmed S.'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of the co-crystalline adduct
 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
 - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              417
_journal_page_last               419
_journal_paper_doi               10.1515/ncrs-2016-0295
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C23 H28 N4 O6 S'
_chemical_formula_weight         488.55
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.657(2)
_cell_angle_beta                 96.902(2)
_cell_angle_gamma                113.010(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3612(3)
_cell_length_b                   9.2370(4)
_cell_length_c                   19.2940(8)
_cell_measurement_reflns_used    7519
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.73
_cell_measurement_theta_min      2.42
_cell_volume                     1186.92(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.1059
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30303
_diffrn_reflns_theta_full        33.81
_diffrn_reflns_theta_max         33.81
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         9535
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                5797
_reflns_number_total             9535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0295_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8106554
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66513(6) 0.30675(4) 0.16721(2) 0.01900(10) Uani 1 1 d . . .
O1 O 0.12768(17) 0.76957(15) 0.40635(6) 0.0273(3) Uani 1 1 d . . .
O2 O 0.5969(2) 0.7260(2) 0.58195(7) 0.0447(4) Uani 1 1 d . . .
O3 O 0.49752(17) 0.15939(13) 0.14076(6) 0.0266(3) Uani 1 1 d . . .
O4 O 0.84453(17) 0.30033(13) 0.20197(6) 0.0243(3) Uani 1 1 d . . .
N1 N 0.3789(2) 0.64607(17) 0.37223(7) 0.0207(3) Uani 1 1 d . . .
N2 N 0.70479(19) 0.39605(15) 0.09792(7) 0.0188(3) Uani 1 1 d D . .
N3 N 0.95744(19) 0.62917(15) 0.16186(6) 0.0182(3) Uani 1 1 d . . .
N4 N 0.86470(19) 0.59954(15) 0.03763(6) 0.0184(3) Uani 1 1 d . . .
C1 C 0.2120(2) 0.79622(18) 0.46866(8) 0.0198(3) Uani 1 1 d . . .
C2 C 0.1479(2) 0.88177(19) 0.52441(9) 0.0228(3) Uani 1 1 d . . .
H2A H 0.0043 0.8580 0.5104 0.027 Uiso 1 1 calc R . .
H2B H 0.2236 0.9976 0.5261 0.027 Uiso 1 1 calc R . .
C3 C 0.1795(2) 0.83781(18) 0.59858(8) 0.0199(3) Uani 1 1 d . . .
C4 C 0.3972(2) 0.8591(2) 0.61719(8) 0.0232(3) Uani 1 1 d . . .
H4A H 0.4843 0.9740 0.6231 0.028 Uiso 1 1 calc R . .
H4B H 0.4145 0.8215 0.6631 0.028 Uiso 1 1 calc R . .
C5 C 0.4672(2) 0.7734(2) 0.56381(8) 0.0246(4) Uani 1 1 d . . .
C6 C 0.3750(2) 0.75059(19) 0.48973(8) 0.0192(3) Uani 1 1 d . . .
C7 C 0.1335(3) 0.9450(2) 0.65153(10) 0.0336(4) Uani 1 1 d . . .
H7A H 0.1496 0.9144 0.6986 0.050 Uiso 1 1 calc R . .
H7B H -0.0044 0.9339 0.6380 0.050 Uiso 1 1 calc R . .
H7C H 0.2258 1.0557 0.6521 0.050 Uiso 1 1 calc R . .
C8 C 0.0369(2) 0.66561(19) 0.59959(9) 0.0228(3) Uani 1 1 d . . .
H8A H 0.0541 0.6380 0.6472 0.034 Uiso 1 1 calc R . .
H8B H 0.0666 0.5951 0.5663 0.034 Uiso 1 1 calc R . .
H8C H -0.1015 0.6534 0.5859 0.034 Uiso 1 1 calc R . .
C9 C 0.4478(2) 0.67876(19) 0.44074(8) 0.0214(3) Uani 1 1 d . . .
H9A H 0.5549 0.6510 0.4575 0.026 Uiso 1 1 calc R . .
C10 C 0.4532(2) 0.57283(18) 0.32229(8) 0.0188(3) Uani 1 1 d . . .
C11 C 0.3207(2) 0.4769(2) 0.26299(8) 0.0221(3) Uani 1 1 d . . .
H11A H 0.1857 0.4658 0.2555 0.027 Uiso 1 1 calc R . .
C12 C 0.3871(2) 0.39800(19) 0.21521(8) 0.0226(3) Uani 1 1 d . . .
H12A H 0.2975 0.3311 0.1749 0.027 Uiso 1 1 calc R . .
C13 C 0.5858(2) 0.41656(17) 0.22612(8) 0.0175(3) Uani 1 1 d . . .
C14 C 0.7192(2) 0.51729(17) 0.28377(8) 0.0177(3) Uani 1 1 d . . .
H14A H 0.8557 0.5323 0.2899 0.021 Uiso 1 1 calc R . .
C15 C 0.6535(2) 0.59579(18) 0.33219(8) 0.0187(3) Uani 1 1 d . . .
H15A H 0.7440 0.6648 0.3719 0.022 Uiso 1 1 calc R . .
C16 C 0.8480(2) 0.54532(17) 0.10072(8) 0.0162(3) Uani 1 1 d . . .
C17 C 1.0896(2) 0.77641(18) 0.16003(8) 0.0192(3) Uani 1 1 d . . .
C18 C 1.1150(2) 0.84027(18) 0.09703(8) 0.0206(3) Uani 1 1 d . . .
H18A H 1.2108 0.9450 0.0967 0.025 Uiso 1 1 calc R . .
C19 C 0.9981(2) 0.74819(18) 0.03536(8) 0.0183(3) Uani 1 1 d . . .
C20 C 1.2065(3) 0.8695(2) 0.22955(9) 0.0306(4) Uani 1 1 d . . .
H20A H 1.1148 0.8631 0.2632 0.046 Uiso 1 1 calc R . .
H20B H 1.2796 0.9808 0.2237 0.046 Uiso 1 1 calc R . .
H20C H 1.3017 0.8256 0.2474 0.046 Uiso 1 1 calc R . .
C21 C 1.0058(3) 0.8047(2) -0.03518(8) 0.0245(3) Uani 1 1 d . . .
H21A H 1.0037 0.7212 -0.0704 0.037 Uiso 1 1 calc R . .
H21B H 1.1290 0.9001 -0.0328 0.037 Uiso 1 1 calc R . .
H21C H 0.8897 0.8297 -0.0485 0.037 Uiso 1 1 calc R . .
O5 O 0.4491(2) 0.22350(18) -0.02319(7) 0.0434(4) Uani 1 1 d . . .
O6 O 0.6369(2) 0.40658(15) -0.08258(7) 0.0342(3) Uani 1 1 d D . .
C22 C 0.3767(3) 0.1725(2) -0.14762(9) 0.0293(4) Uani 1 1 d . . .
H22A H 0.3936 0.2371 -0.1861 0.044 Uiso 1 1 calc R . .
H22B H 0.2348 0.1238 -0.1433 0.044 Uiso 1 1 calc R . .
H22C H 0.4247 0.0891 -0.1576 0.044 Uiso 1 1 calc R . .
C23 C 0.4940(2) 0.2753(2) -0.08033(8) 0.0225(3) Uani 1 1 d . . .
H1N1 H 0.280(4) 0.672(3) 0.3584(12) 0.049(7) Uiso 1 1 d . . .
H1N2 H 0.611(4) 0.335(4) 0.0535(10) 0.113(12) Uiso 1 1 d D . .
H1O6 H 0.725(5) 0.483(4) -0.0403(13) 0.146(16) Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 S1 O3 117.99(7) . .
O4 S1 N2 111.22(7) . .
O3 S1 N2 103.44(7) . .
O4 S1 C13 108.25(7) . .
O3 S1 C13 107.55(7) . .
N2 S1 C13 107.94(7) . .
C9 N1 C10 124.66(14) . .
C9 N1 H1N1 115.6(15) . .
C10 N1 H1N1 119.7(15) . .
C16 N2 S1 122.54(11) . .
C16 N2 H1N2 123(2) . .
S1 N2 H1N2 115(2) . .
C16 N3 C17 117.11(13) . .
C19 N4 C16 118.99(13) . .
O1 C1 C6 121.79(15) . .
O1 C1 C2 119.99(14) . .
C6 C1 C2 118.21(13) . .
C1 C2 C3 114.39(13) . .
C1 C2 H2A 108.7 . .
C3 C2 H2A 108.7 . .
C1 C2 H2B 108.7 . .
C3 C2 H2B 108.7 . .
H2A C2 H2B 107.6 . .
C7 C3 C8 108.62(13) . .
C7 C3 C4 110.15(14) . .
C8 C3 C4 110.64(13) . .
C7 C3 C2 109.64(13) . .
C8 C3 C2 109.24(13) . .
C4 C3 C2 108.53(12) . .
C5 C4 C3 114.96(13) . .
C5 C4 H4A 108.5 . .
C3 C4 H4A 108.5 . .
C5 C4 H4B 108.5 . .
C3 C4 H4B 108.5 . .
H4A C4 H4B 107.5 . .
O2 C5 C6 121.79(16) . .
O2 C5 C4 120.83(15) . .
C6 C5 C4 117.37(14) . .
C9 C6 C1 121.22(14) . .
C9 C6 C5 116.80(14) . .
C1 C6 C5 121.95(14) . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C3 C8 H8A 109.5 . .
C3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 C6 124.68(15) . .
N1 C9 H9A 117.7 . .
C6 C9 H9A 117.7 . .
C15 C10 C11 120.89(15) . .
C15 C10 N1 120.87(14) . .
C11 C10 N1 118.24(14) . .
C12 C11 C10 119.36(14) . .
C12 C11 H11A 120.3 . .
C10 C11 H11A 120.3 . .
C11 C12 C13 119.88(14) . .
C11 C12 H12A 120.1 . .
C13 C12 H12A 120.1 . .
C14 C13 C12 120.55(14) . .
C14 C13 S1 120.10(12) . .
C12 C13 S1 119.33(12) . .
C15 C14 C13 119.91(14) . .
C15 C14 H14A 120.0 . .
C13 C14 H14A 120.0 . .
C14 C15 C10 119.32(14) . .
C14 C15 H15A 120.3 . .
C10 C15 H15A 120.3 . .
N3 C16 N4 124.22(13) . .
N3 C16 N2 121.11(13) . .
N4 C16 N2 114.66(13) . .
N3 C17 C18 121.86(14) . .
N3 C17 C20 116.05(13) . .
C18 C17 C20 122.08(14) . .
C19 C18 C17 118.57(14) . .
C19 C18 H18A 120.7 . .
C17 C18 H18A 120.7 . .
N4 C19 C18 119.23(13) . .
N4 C19 C21 116.99(13) . .
C18 C19 C21 123.76(14) . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C23 O6 H1O6 125(2) . .
C23 C22 H22A 109.5 . .
C23 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C23 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O6 C23 O5 123.03(15) . .
O6 C23 C22 119.16(15) . .
O5 C23 C22 117.76(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O4 1.4326(12) .
S1 O3 1.4348(11) .
S1 N2 1.6240(13) .
S1 C13 1.7599(16) .
O1 C1 1.2426(18) .
O2 C5 1.223(2) .
N1 C9 1.323(2) .
N1 C10 1.413(2) .
N1 H1N1 0.87(2) .
N2 C16 1.3614(18) .
N2 H1N2 1.004(5) .
N3 C16 1.3326(19) .
N3 C17 1.3338(18) .
N4 C19 1.3482(19) .
N4 C16 1.3545(18) .
C1 C6 1.445(2) .
C1 C2 1.510(2) .
C2 C3 1.535(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C7 1.523(2) .
C3 C8 1.529(2) .
C3 C4 1.529(2) .
C4 C5 1.506(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.468(2) .
C6 C9 1.385(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9500 .
C10 C15 1.391(2) .
C10 C11 1.392(2) .
C11 C12 1.378(2) .
C11 H11A 0.9500 .
C12 C13 1.391(2) .
C12 H12A 0.9500 .
C13 C14 1.387(2) .
C14 C15 1.381(2) .
C14 H14A 0.9500 .
C15 H15A 0.9500 .
C17 C18 1.395(2) .
C17 C20 1.495(2) .
C18 C19 1.377(2) .
C18 H18A 0.9500 .
C19 C21 1.496(2) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
O5 C23 1.266(2) .
O6 C23 1.266(2) .
O6 H1O6 1.001(5) .
C22 C23 1.490(2) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
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
O4 S1 N2 C16 -55.38(14) . . . .
O3 S1 N2 C16 177.00(12) . . . .
C13 S1 N2 C16 63.22(14) . . . .
O1 C1 C2 C3 151.18(14) . . . .
C6 C1 C2 C3 -30.21(19) . . . .
C1 C2 C3 C7 173.26(14) . . . .
C1 C2 C3 C8 -67.82(17) . . . .
C1 C2 C3 C4 52.90(17) . . . .
C7 C3 C4 C5 -173.24(14) . . . .
C8 C3 C4 C5 66.65(17) . . . .
C2 C3 C4 C5 -53.19(17) . . . .
C3 C4 C5 O2 -150.19(17) . . . .
C3 C4 C5 C6 30.3(2) . . . .
O1 C1 C6 C9 1.8(2) . . . .
C2 C1 C6 C9 -176.82(14) . . . .
O1 C1 C6 C5 -176.34(15) . . . .
C2 C1 C6 C5 5.1(2) . . . .
O2 C5 C6 C9 -2.7(2) . . . .
C4 C5 C6 C9 176.81(14) . . . .
O2 C5 C6 C1 175.52(16) . . . .
C4 C5 C6 C1 -5.0(2) . . . .
C10 N1 C9 C6 179.99(14) . . . .
C1 C6 C9 N1 0.2(2) . . . .
C5 C6 C9 N1 178.39(15) . . . .
C9 N1 C10 C15 -31.1(2) . . . .
C9 N1 C10 C11 148.74(16) . . . .
C15 C10 C11 C12 3.0(2) . . . .
N1 C10 C11 C12 -176.90(14) . . . .
C10 C11 C12 C13 -0.8(2) . . . .
C11 C12 C13 C14 -1.8(2) . . . .
C11 C12 C13 S1 176.57(12) . . . .
O4 S1 C13 C14 19.20(14) . . . .
O3 S1 C13 C14 147.71(12) . . . .
N2 S1 C13 C14 -101.28(13) . . . .
O4 S1 C13 C12 -159.13(12) . . . .
O3 S1 C13 C12 -30.63(14) . . . .
N2 S1 C13 C12 80.39(13) . . . .
C12 C13 C14 C15 2.3(2) . . . .
S1 C13 C14 C15 -176.05(11) . . . .
C13 C14 C15 C10 -0.2(2) . . . .
C11 C10 C15 C14 -2.5(2) . . . .
N1 C10 C15 C14 177.39(13) . . . .
C17 N3 C16 N4 0.8(2) . . . .
C17 N3 C16 N2 -177.73(14) . . . .
C19 N4 C16 N3 -0.7(2) . . . .
C19 N4 C16 N2 177.88(13) . . . .
S1 N2 C16 N3 -3.3(2) . . . .
S1 N2 C16 N4 178.05(11) . . . .
C16 N3 C17 C18 -0.7(2) . . . .
C16 N3 C17 C20 178.40(15) . . . .
N3 C17 C18 C19 0.6(2) . . . .
C20 C17 C18 C19 -178.45(16) . . . .
C16 N4 C19 C18 0.6(2) . . . .
C16 N4 C19 C21 -177.87(14) . . . .
C17 C18 C19 N4 -0.5(2) . . . .
C17 C18 C19 C21 177.81(15) . . . .
