#------------------------------------------------------------------------------
#$Date: 2022-11-01 14:35:34 +0200 (Tue, 01 Nov 2022) $
#$Revision: 278899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567886.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_1567886
loop_
_publ_author_name
'Mohamed-Ezzat, Reham A.'
'Kariuki, Benson M.'
'Azzam, Rasha A.'
_publ_section_title
;
 Morpholin-4-ium
 [5-cyano-6-(4-methylphenyl)-4-(morpholin-4-yl)pyrimidin-2-yl](phenylsulfonyl)amide
;
_journal_coeditor_code           HB4417
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x221033
_journal_paper_doi               10.1107/S2414314622010331
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C4 H10 N O +, C22 H20 N5 O3 S -'
_chemical_formula_moiety         'C4 H10 N O +, C22 H20 N5 O3 S -'
_chemical_formula_sum            'C26 H30 N6 O4 S'
_chemical_formula_weight         522.62
_chemical_name_systematic
'Morpholin-4-ium [5-cyano-6-(4-methylphenyl)-4-(morpholin-4-yl)pyrimidin-2-yl](phenylsulfonyl)amide'
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 99.964(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4177(4)
_cell_length_b                   11.7104(3)
_cell_length_c                   21.5388(7)
_cell_measurement_reflns_used    9606
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.7040
_cell_measurement_theta_min      3.8190
_cell_volume                     2588.00(15)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  '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  0.0264
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24156
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.618
_diffrn_reflns_theta_min         3.366
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0473
_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)+(0.0510P)²+1.0570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                4792
_reflns_number_total             6299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4417.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1567886
_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   0.907
_shelx_estimated_absorpt_t_max   0.964
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_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 0.39746(16) 0.55594(15) 0.26967(8) 0.0364(4) Uani d 1 . .
C C2 0.4004(2) 0.6037(2) 0.21176(9) 0.0554(5) Uani d 1 . .
H H2 0.431138 0.677645 0.208445 0.066 Uiso calc 1 . .
C C3 0.3566(3) 0.5391(3) 0.15822(11) 0.0751(8) Uani d 1 . .
H H3 0.355923 0.570912 0.118600 0.090 Uiso calc 1 . .
C C4 0.3144(2) 0.4296(3) 0.16295(12) 0.0723(8) Uani d 1 . .
H H4 0.287794 0.386557 0.126719 0.087 Uiso calc 1 . .
C C5 0.3111(2) 0.3831(2) 0.22091(13) 0.0661(7) Uani d 1 . .
H H5 0.281315 0.308830 0.224035 0.079 Uiso calc 1 . .
C C6 0.3517(2) 0.44611(17) 0.27452(10) 0.0512(5) Uani d 1 . .
H H6 0.348518 0.414928 0.313928 0.061 Uiso calc 1 . .
C C7 0.64862(16) 0.52093(14) 0.37849(7) 0.0329(4) Uani d 1 . .
C C8 0.80885(17) 0.51091(14) 0.31695(8) 0.0338(4) Uani d 1 . .
C C9 0.88299(16) 0.43727(14) 0.36271(8) 0.0339(4) Uani d 1 . .
C C10 0.82690(16) 0.40889(14) 0.41528(8) 0.0338(4) Uani d 1 . .
C C11 0.7780(2) 0.64082(18) 0.22731(10) 0.0513(5) Uani d 1 . .
H H11A 0.728043 0.684328 0.253162 0.062 Uiso calc 1 . .
H H11B 0.717953 0.607433 0.192622 0.062 Uiso calc 1 . .
C C12 0.8723(3) 0.7172(2) 0.20250(13) 0.0690(7) Uani d 1 . .
H H12A 0.824400 0.776570 0.176883 0.083 Uiso calc 1 . .
H H12B 0.928029 0.753801 0.237609 0.083 Uiso calc 1 . .
C C13 1.0217(3) 0.5704(3) 0.20295(15) 0.0853(9) Uani d 1 . .
H H13A 1.080848 0.605144 0.237535 0.102 Uiso calc 1 . .
H H13B 1.073593 0.529160 0.177068 0.102 Uiso calc 1 . .
C C14 0.9353(2) 0.48884(19) 0.22871(10) 0.0526(5) Uani d 1 . .
H H14A 0.882101 0.447882 0.194430 0.063 Uiso calc 1 . .
H H14B 0.987657 0.433602 0.255552 0.063 Uiso calc 1 . .
C C15 1.01574(18) 0.40786(16) 0.36277(9) 0.0408(4) Uani d 1 . .
C C16 0.89636(17) 0.33313(15) 0.46580(8) 0.0365(4) Uani d 1 . .
C C17 0.95107(19) 0.23040(16) 0.45184(9) 0.0443(4) Uani d 1 . .
H H17 0.940804 0.205576 0.410260 0.053 Uiso calc 1 . .
C C18 1.0208(2) 0.16462(18) 0.49937(10) 0.0509(5) Uani d 1 . .
H H18 1.055758 0.095288 0.489394 0.061 Uiso calc 1 . .
C C19 1.0396(2) 0.20040(19) 0.56175(10) 0.0516(5) Uani d 1 . .
C C20 0.9792(2) 0.29990(19) 0.57567(9) 0.0538(5) Uani d 1 . .
H H20 0.986764 0.322991 0.617454 0.065 Uiso calc 1 . .
C C21 0.9077(2) 0.36606(17) 0.52859(9) 0.0455(4) Uani d 1 . .
H H21 0.867217 0.432463 0.538977 0.055 Uiso calc 1 . .
C C22 1.1275(3) 0.1340(3) 0.61238(13) 0.0786(8) Uani d 1 . .
H H22A 1.212050 0.169081 0.620502 0.118 Uiso calc 1 . .
H H22B 1.135534 0.056836 0.598458 0.118 Uiso calc 1 . .
H H22C 1.090822 0.133863 0.650304 0.118 Uiso calc 1 . .
C C23 0.5070(3) 0.14024(18) 0.53116(11) 0.0636(6) Uani d 1 . .
H H23A 0.543086 0.063991 0.537983 0.076 Uiso calc 1 . .
H H23B 0.494986 0.170698 0.571640 0.076 Uiso calc 1 . .
C C24 0.6004(2) 0.21430(19) 0.50402(11) 0.0567(5) Uani d 1 . .
H H24A 0.682757 0.217948 0.532919 0.068 Uiso calc 1 . .
H H24B 0.616321 0.182007 0.464587 0.068 Uiso calc 1 . .
C C25 0.3288(2) 0.2453(2) 0.48171(14) 0.0689(7) Uani d 1 . .
H H25A 0.316172 0.275345 0.522183 0.083 Uiso calc 1 . .
H H25B 0.244099 0.240285 0.454790 0.083 Uiso calc 1 . .
C C26 0.4142(2) 0.32545(19) 0.45255(11) 0.0546(5) Uani d 1 . .
H H26A 0.422374 0.298634 0.410798 0.066 Uiso calc 1 . .
H H26B 0.375257 0.400904 0.448447 0.066 Uiso calc 1 . .
O O1 0.32666(13) 0.65594(12) 0.36557(6) 0.0501(3) Uani d 1 . .
O O2 0.50656(15) 0.73961(11) 0.32196(7) 0.0514(4) Uani d 1 . .
O O3 0.9501(2) 0.65779(19) 0.16615(10) 0.0938(7) Uani d 1 . .
O O4 0.38439(18) 0.13440(13) 0.49027(8) 0.0684(5) Uani d 1 . .
S S1 0.44351(4) 0.63797(4) 0.33901(2) 0.03651(13) Uani d 1 . .
N N1 0.53251(14) 0.55919(12) 0.39007(6) 0.0361(3) Uani d 1 . .
N N2 0.71172(14) 0.44877(12) 0.42381(6) 0.0356(3) Uani d 1 . .
N N3 0.69318(14) 0.54979(12) 0.32594(6) 0.0358(3) Uani d 1 . .
N N4 0.85165(15) 0.55056(13) 0.26502(7) 0.0420(4) Uani d 1 . .
N N5 1.12314(18) 0.38456(18) 0.36510(9) 0.0609(5) Uani d 1 . .
N N6 0.54503(16) 0.33128(13) 0.49288(7) 0.0438(4) Uani d 1 . .
H H6A 0.538585 0.363750 0.529578 0.053 Uiso calc 1 . .
H H6B 0.597821 0.373892 0.474098 0.053 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 0.0033 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'
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'
N N 0.0061 0.0033 '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 . . 120.69(18) ?
C2 C1 S1 . . 120.00(15) ?
C6 C1 S1 . . 119.20(14) ?
C1 C2 C3 . . 118.5(2) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C4 C3 C2 . . 120.9(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.1(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.1(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 119.8(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N3 C7 N1 . . 121.60(15) ?
N3 C7 N2 . . 124.35(16) ?
N1 C7 N2 . . 114.01(15) ?
N3 C8 N4 . . 115.94(15) ?
N3 C8 C9 . . 119.96(15) ?
N4 C8 C9 . . 124.00(16) ?
C10 C9 C15 . . 118.84(15) ?
C10 C9 C8 . . 116.65(15) ?
C15 C9 C8 . . 123.66(16) ?
N2 C10 C9 . . 122.75(15) ?
N2 C10 C16 . . 116.35(16) ?
C9 C10 C16 . . 120.89(16) ?
N4 C11 C12 . . 108.46(17) ?
N4 C11 H11A . . 110.0 ?
C12 C11 H11A . . 110.0 ?
N4 C11 H11B . . 110.0 ?
C12 C11 H11B . . 110.0 ?
H11A C11 H11B . . 108.4 ?
O3 C12 C11 . . 112.4(2) ?
O3 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
O3 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.9 ?
O3 C13 C14 . . 112.2(2) ?
O3 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
O3 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
N4 C14 C13 . . 109.8(2) ?
N4 C14 H14A . . 109.7 ?
C13 C14 H14A . . 109.7 ?
N4 C14 H14B . . 109.7 ?
C13 C14 H14B . . 109.7 ?
H14A C14 H14B . . 108.2 ?
N5 C15 C9 . . 177.6(2) ?
C17 C16 C21 . . 118.84(16) ?
C17 C16 C10 . . 121.61(16) ?
C21 C16 C10 . . 119.55(16) ?
C18 C17 C16 . . 120.40(19) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 121.1(2) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C20 C19 C18 . . 118.13(18) ?
C20 C19 C22 . . 121.3(2) ?
C18 C19 C22 . . 120.6(2) ?
C19 C20 C21 . . 121.3(2) ?
C19 C20 H20 . . 119.3 ?
C21 C20 H20 . . 119.3 ?
C20 C21 C16 . . 120.01(19) ?
C20 C21 H21 . . 120.0 ?
C16 C21 H21 . . 120.0 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O4 C23 C24 . . 111.16(18) ?
O4 C23 H23A . . 109.4 ?
C24 C23 H23A . . 109.4 ?
O4 C23 H23B . . 109.4 ?
C24 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
N6 C24 C23 . . 109.7(2) ?
N6 C24 H24A . . 109.7 ?
C23 C24 H24A . . 109.7 ?
N6 C24 H24B . . 109.7 ?
C23 C24 H24B . . 109.7 ?
H24A C24 H24B . . 108.2 ?
O4 C25 C26 . . 111.5(2) ?
O4 C25 H25A . . 109.3 ?
C26 C25 H25A . . 109.3 ?
O4 C25 H25B . . 109.3 ?
C26 C25 H25B . . 109.3 ?
H25A C25 H25B . . 108.0 ?
N6 C26 C25 . . 109.50(18) ?
N6 C26 H26A . . 109.8 ?
C25 C26 H26A . . 109.8 ?
N6 C26 H26B . . 109.8 ?
C25 C26 H26B . . 109.8 ?
H26A C26 H26B . . 108.2 ?
C12 O3 C13 . . 110.05(19) ?
C25 O4 C23 . . 109.80(17) ?
O2 S1 O1 . . 115.69(9) ?
O2 S1 N1 . . 114.60(8) ?
O1 S1 N1 . . 103.82(8) ?
O2 S1 C1 . . 107.62(9) ?
O1 S1 C1 . . 106.78(8) ?
N1 S1 C1 . . 107.86(8) ?
C7 N1 S1 . . 119.59(12) ?
C10 N2 C7 . . 116.83(15) ?
C8 N3 C7 . . 119.39(15) ?
C8 N4 C14 . . 125.78(15) ?
C8 N4 C11 . . 119.25(15) ?
C14 N4 C11 . . 111.35(15) ?
C26 N6 C24 . . 110.01(16) ?
C26 N6 H6A . . 109.7 ?
C24 N6 H6A . . 109.7 ?
C26 N6 H6B . . 109.7 ?
C24 N6 H6B . . 109.7 ?
H6A N6 H6B . . 108.2 ?
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 . 1.372(3) ?
C1 C6 . 1.382(3) ?
C1 S1 . 1.7708(17) ?
C2 C3 . 1.389(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N3 . 1.339(2) ?
C7 N1 . 1.353(2) ?
C7 N2 . 1.370(2) ?
C8 N3 . 1.333(2) ?
C8 N4 . 1.356(2) ?
C8 C9 . 1.431(2) ?
C9 C10 . 1.401(2) ?
C9 C15 . 1.425(3) ?
C10 N2 . 1.330(2) ?
C10 C16 . 1.491(2) ?
C11 N4 . 1.466(2) ?
C11 C12 . 1.494(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O3 . 1.405(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 O3 . 1.423(3) ?
C13 C14 . 1.484(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 N4 . 1.459(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 N5 . 1.144(2) ?
C16 C17 . 1.386(3) ?
C16 C21 . 1.392(3) ?
C17 C18 . 1.383(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.389(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.381(3) ?
C19 C22 . 1.513(3) ?
C20 C21 . 1.387(3) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 O4 . 1.423(3) ?
C23 C24 . 1.495(3) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 N6 . 1.490(3) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 O4 . 1.421(3) ?
C25 C26 . 1.504(3) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 N6 . 1.486(3) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
O1 S1 . 1.4472(14) ?
O2 S1 . 1.4375(14) ?
S1 N1 . 1.6023(14) ?
N6 H6A . 0.8900 ?
N6 H6B . 0.8900 ?
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 H6A O1 3_666 0.89 2.45 3.113(2) 131 yes
N6 H6A N1 3_666 0.89 2.19 3.059(2) 165 yes
N6 H6B N2 . 0.89 1.95 2.831(2) 171 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
C7 N1 S1 C1 . . . . 63.74(15) ?
N3 C7 N1 S1 . . . . 1.9(2) ?
