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#$Date: 2024-06-28 04:07:51 +0300 (Fri, 28 Jun 2024) $
#$Revision: 292632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/89/7248910.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_7248910
loop_
_publ_author_name
'Tawfeek, Hendawy N.'
'Abdelmoez, Alshaimaa'
'Dahlous, Kholood A.'
'Youssif, Bahaa G. M.'
'Bräse, Stefan'
'Rissanen, Kari'
'Nieger, Martin'
'El-Sheref, Essmat M.'
_publ_section_title
;
 Convenient synthesis and X-ray determination of
 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative
 activity
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              17866
_journal_page_last               17876
_journal_paper_doi               10.1039/D4RA02531H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 N3 S, Br'
_chemical_formula_sum            'C15 H14 Br N3 S'
_chemical_formula_weight         348.26
_chemical_name_systematic
;
5-phenyl-2-(phenylamino)-6H-1,3,4-thiadiazin-3-ium
;
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-01-30 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.364(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9077(1)
_cell_length_b                   9.1847(1)
_cell_length_c                   18.1367(2)
_cell_measurement_reflns_used    14033
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      78.8
_cell_measurement_theta_min      2.3
_cell_volume                     1481.29(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'omega scans, 0.5 deg.'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16484
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.309
_diffrn_reflns_theta_min         5.401
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       blocks
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00182(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0202
_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)+(0.0219P)²+1.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             3177
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02531h2.cif
_cod_data_source_block           sb1527_hy
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248910
_shelx_shelxl_version_number     2014/7
_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   0.459
_shelx_estimated_absorpt_t_max   0.558
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_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
Br1 Br 0.25957(2) 0.31608(2) 0.44651(2) 0.01901(7) Uani 1 1 d . . . . .
S1 S 0.87653(4) 0.32924(4) 0.46049(2) 0.01815(9) Uani 1 1 d . . . . .
C2 C 0.68364(16) 0.34164(16) 0.46581(8) 0.0162(3) Uani 1 1 d . . . . .
N3 N 0.59958(13) 0.40419(14) 0.41130(6) 0.0174(2) Uani 1 1 d D . . . .
H3 H 0.5028(16) 0.395(2) 0.4142(10) 0.021 Uiso 1 1 d D U . . .
N4 N 0.64107(13) 0.42265(14) 0.33889(6) 0.0173(2) Uani 1 1 d . . . . .
C5 C 0.78026(15) 0.45212(16) 0.33009(8) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.89042(16) 0.47704(17) 0.39483(8) 0.0188(3) Uani 1 1 d . . . . .
H6A H 0.8683 0.5708 0.4189 0.023 Uiso 1 1 calc R U . . .
H6B H 0.9938 0.4817 0.3777 0.023 Uiso 1 1 calc R U . . .
N21 N 0.61397(14) 0.28836(14) 0.52253(7) 0.0174(2) Uani 1 1 d D . . . .
H21 H 0.5178(17) 0.291(2) 0.5179(10) 0.021 Uiso 1 1 d D U . . .
C21 C 0.68529(16) 0.23158(16) 0.58919(8) 0.0179(3) Uani 1 1 d . . . . .
C22 C 0.79148(17) 0.12128(17) 0.58685(9) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.8188 0.0830 0.5409 0.027 Uiso 1 1 calc R U . . .
C23 C 0.85738(18) 0.06763(19) 0.65280(10) 0.0291(4) Uani 1 1 d . . . . .
H23 H 0.9317 -0.0065 0.6520 0.035 Uiso 1 1 calc R U . . .
C24 C 0.81487(19) 0.12212(19) 0.71968(9) 0.0295(4) Uani 1 1 d . . . . .
H24 H 0.8608 0.0858 0.7646 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7058(2) 0.22914(18) 0.72140(9) 0.0269(3) Uani 1 1 d . . . . .
H25 H 0.6756 0.2646 0.7675 0.032 Uiso 1 1 calc R U . . .
C26 C 0.64039(18) 0.28487(17) 0.65599(8) 0.0208(3) Uani 1 1 d . . . . .
H26 H 0.5658 0.3586 0.6570 0.025 Uiso 1 1 calc R U . . .
C51 C 0.82514(16) 0.46556(16) 0.25336(8) 0.0174(3) Uani 1 1 d . . . . .
C52 C 0.94752(17) 0.55150(17) 0.23639(9) 0.0209(3) Uani 1 1 d . . . . .
H52 H 1.0068 0.5978 0.2748 0.025 Uiso 1 1 calc R U . . .
C53 C 0.98283(18) 0.56951(18) 0.16333(9) 0.0254(3) Uani 1 1 d . . . . .
H53 H 1.0652 0.6293 0.1518 0.030 Uiso 1 1 calc R U . . .
C54 C 0.89789(19) 0.50030(19) 0.10735(9) 0.0272(3) Uani 1 1 d . . . . .
H54 H 0.9223 0.5129 0.0575 0.033 Uiso 1 1 calc R U . . .
C55 C 0.77736(19) 0.41260(19) 0.12366(9) 0.0267(3) Uani 1 1 d . . . . .
H55 H 0.7200 0.3646 0.0851 0.032 Uiso 1 1 calc R U . . .
C56 C 0.74090(17) 0.39518(18) 0.19642(8) 0.0221(3) Uani 1 1 d . . . . .
H56 H 0.6584 0.3352 0.2076 0.027 Uiso 1 1 calc R U . . .
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'
Br Br -0.6763 1.2805 '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'
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 C6 95.36(7) . . ?
N21 C2 N3 117.77(13) . . ?
N21 C2 S1 122.04(11) . . ?
N3 C2 S1 120.19(11) . . ?
C2 N3 N4 125.55(12) . . ?
C2 N3 H3 115.5(12) . . ?
N4 N3 H3 112.7(12) . . ?
C5 N4 N3 116.88(12) . . ?
N4 C5 C51 116.78(12) . . ?
N4 C5 C6 121.62(13) . . ?
C51 C5 C6 121.57(12) . . ?
C5 C6 S1 109.41(10) . . ?
C5 C6 H6A 109.8 . . ?
S1 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
S1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C2 N21 C21 125.83(12) . . ?
C2 N21 H21 115.1(12) . . ?
C21 N21 H21 119.0(12) . . ?
C26 C21 C22 121.06(14) . . ?
C26 C21 N21 118.22(13) . . ?
C22 C21 N21 120.65(13) . . ?
C21 C22 C23 119.08(15) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 120.11(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.32(15) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.17(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.22(15) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C52 C51 C56 119.39(14) . . ?
C52 C51 C5 120.94(13) . . ?
C56 C51 C5 119.63(13) . . ?
C53 C52 C51 120.10(15) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C54 C53 C52 120.00(15) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 120.42(14) . . ?
C53 C54 H54 119.8 . . ?
C55 C54 H54 119.8 . . ?
C56 C55 C54 119.82(15) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C55 C56 C51 120.26(15) . . ?
C55 C56 H56 119.9 . . ?
C51 C56 H56 119.9 . . ?
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 1.7304(14) . ?
S1 C6 1.8148(15) . ?
C2 N21 1.3259(19) . ?
C2 N3 1.3346(18) . ?
N3 N4 1.3954(16) . ?
N3 H3 0.871(14) . ?
N4 C5 1.2880(18) . ?
C5 C51 1.4753(19) . ?
C5 C6 1.5029(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N21 C21 1.4306(18) . ?
N21 H21 0.857(15) . ?
C21 C26 1.387(2) . ?
C21 C22 1.388(2) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C51 C52 1.395(2) . ?
C51 C56 1.399(2) . ?
C52 C53 1.390(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.385(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.388(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.386(2) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 Br1 0.871(14) 2.391(15) 3.2346(12) 163.3(17) .
N21 H21 Br1 0.857(15) 2.583(15) 3.3795(12) 155.2(16) .
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
C6 S1 C2 N21 -159.15(13) . . . . ?
C6 S1 C2 N3 21.95(13) . . . . ?
N21 C2 N3 N4 -157.72(13) . . . . ?
S1 C2 N3 N4 21.2(2) . . . . ?
C2 N3 N4 C5 -36.6(2) . . . . ?
N3 N4 C5 C51 177.54(12) . . . . ?
N3 N4 C5 C6 -4.6(2) . . . . ?
N4 C5 C6 S1 50.04(17) . . . . ?
C51 C5 C6 S1 -132.24(12) . . . . ?
C2 S1 C6 C5 -51.66(11) . . . . ?
N3 C2 N21 C21 -173.04(14) . . . . ?
S1 C2 N21 C21 8.0(2) . . . . ?
C2 N21 C21 C26 128.30(16) . . . . ?
C2 N21 C21 C22 -54.7(2) . . . . ?
C26 C21 C22 C23 -2.4(2) . . . . ?
N21 C21 C22 C23 -179.32(14) . . . . ?
C21 C22 C23 C24 1.3(2) . . . . ?
C22 C23 C24 C25 0.6(2) . . . . ?
C23 C24 C25 C26 -1.4(2) . . . . ?
C22 C21 C26 C25 1.6(2) . . . . ?
N21 C21 C26 C25 178.65(14) . . . . ?
C24 C25 C26 C21 0.3(2) . . . . ?
N4 C5 C51 C52 153.46(14) . . . . ?
C6 C5 C51 C52 -24.4(2) . . . . ?
N4 C5 C51 C56 -24.4(2) . . . . ?
C6 C5 C51 C56 157.81(14) . . . . ?
C56 C51 C52 C53 1.5(2) . . . . ?
C5 C51 C52 C53 -176.31(14) . . . . ?
C51 C52 C53 C54 -1.0(2) . . . . ?
C52 C53 C54 C55 -0.1(2) . . . . ?
C53 C54 C55 C56 0.6(2) . . . . ?
C54 C55 C56 C51 0.0(2) . . . . ?
C52 C51 C56 C55 -1.0(2) . . . . ?
C5 C51 C56 C55 176.84(14) . . . . ?
