#------------------------------------------------------------------------------
#$Date: 2023-06-06 08:32:55 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022741.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_2022741
loop_
_publ_author_name
'Abdallah, Amira E. M.'
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 N-[3-(benzo[d]thia-zol-2-yl)-6-bromo-2H-chromen-2-yl-idene]-4-methyl-benzenamine.
;
_journal_coeditor_code           YZ2032
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              441
_journal_page_last               445
_journal_paper_doi               10.1107/S2056989023002979
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C23 H15 Br N2 O S'
_chemical_formula_moiety         'C23 H15 Br N2 O S'
_chemical_formula_sum            'C23 H15 Br N2 O S'
_chemical_formula_weight         447.34
_chemical_name_systematic
N-[3-(Benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                104.5034(16)
_cell_angle_beta                 90.2462(12)
_cell_angle_gamma                103.9961(14)
_cell_formula_units_Z            2
_cell_length_a                   7.34138(10)
_cell_length_b                   10.6720(2)
_cell_length_c                   12.9247(2)
_cell_measurement_reflns_used    55045
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.9980
_cell_measurement_theta_min      2.2740
_cell_volume                     948.97(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      100.00(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            126966
_diffrn_reflns_theta_full        40.500
_diffrn_reflns_theta_max         41.276
_diffrn_reflns_theta_min         2.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            'yellow-orange dichroic'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.642
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         12477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.270
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0329P)²+0.3775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                11717
_reflns_number_total             12477
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2032sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022741.cif.'
_cod_database_code               2022741
_cod_database_fobs_code          2022741
_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   0.657
_shelx_estimated_absorpt_t_max   0.770
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.45005(3) 0.22816(2) 0.24952(2) 0.01102(4) Uani d 1 . .
C C2 0.53265(12) 0.27006(9) 0.38418(7) 0.00988(12) Uani d 1 . .
N N3 0.47875(11) 0.17627(8) 0.43436(6) 0.01092(11) Uani d 1 . .
C C3A 0.36335(12) 0.06293(9) 0.36717(7) 0.01059(12) Uani d 1 . .
C C4 0.27384(14) -0.05271(10) 0.39829(8) 0.01396(14) Uani d 1 . .
H H4 0.294443 -0.059470 0.469083 0.017 Uiso calc 1 . .
C C5 0.15488(14) -0.15658(10) 0.32326(9) 0.01606(16) Uani d 1 . .
H H5 0.091595 -0.234805 0.343368 0.019 Uiso calc 1 . .
C C6 0.12611(14) -0.14821(10) 0.21763(9) 0.01639(16) Uani d 1 . .
H H6 0.044937 -0.221294 0.167457 0.020 Uiso calc 1 . .
C C7 0.21439(14) -0.03497(10) 0.18570(8) 0.01469(15) Uani d 1 . .
H H7 0.195092 -0.029543 0.114386 0.018 Uiso calc 1 . .
C C7A 0.33289(12) 0.07121(9) 0.26171(7) 0.01109(13) Uani d 1 . .
C C8 0.65444(12) 0.40075(9) 0.44104(7) 0.01000(12) Uani d 1 . .
C C9 0.69589(12) 0.51144(9) 0.39019(7) 0.01044(12) Uani d 1 . .
O O1 0.81113(10) 0.63197(7) 0.44747(6) 0.01236(11) Uani d 1 . .
N N9 0.62892(12) 0.49654(8) 0.29581(7) 0.01224(12) Uani d 1 . .
C C10 0.87706(12) 0.65155(9) 0.55151(7) 0.01079(12) Uani d 1 . .
C C11 0.98434(13) 0.77861(9) 0.60325(8) 0.01284(14) Uani d 1 . .
H H11 1.010923 0.847551 0.567020 0.015 Uiso calc 1 . .
C C12 1.05226(13) 0.80324(10) 0.70912(8) 0.01385(14) Uani d 1 . .
H H12 1.126245 0.889327 0.745864 0.017 Uiso calc 1 . .
C C13 1.01084(13) 0.70054(10) 0.76081(8) 0.01306(14) Uani d 1 . .
Br Br1 1.09469(2) 0.73707(2) 0.90683(2) 0.01723(3) Uani d 1 . .
C C14 0.90564(13) 0.57339(9) 0.70921(8) 0.01269(13) Uani d 1 . .
H H14 0.880313 0.504533 0.745531 0.015 Uiso calc 1 . .
C C15 0.83692(12) 0.54769(9) 0.60237(7) 0.01077(12) Uani d 1 . .
C C16 0.72340(12) 0.41962(9) 0.54312(7) 0.01106(13) Uani d 1 . .
H H16 0.696241 0.347267 0.575708 0.013 Uiso calc 1 . .
C C17 0.64703(13) 0.59939(9) 0.24293(7) 0.01134(13) Uani d 1 . .
C C18 0.66395(14) 0.56395(10) 0.13211(8) 0.01423(14) Uani d 1 . .
H H18 0.674436 0.476506 0.097566 0.017 Uiso calc 1 . .
C C19 0.66550(15) 0.65591(10) 0.07226(8) 0.01490(15) Uani d 1 . .
H H19 0.680212 0.631073 -0.002518 0.018 Uiso calc 1 . .
C C20 0.64577(13) 0.78423(10) 0.12042(8) 0.01351(14) Uani d 1 . .
C C21 0.62680(14) 0.81793(10) 0.23071(8) 0.01380(14) Uani d 1 . .
H H21 0.611872 0.904390 0.264656 0.017 Uiso calc 1 . .
C C22 0.62919(13) 0.72820(9) 0.29233(8) 0.01265(13) Uani d 1 . .
H H22 0.618755 0.754253 0.367493 0.015 Uiso calc 1 . .
C C23 0.64635(18) 0.88259(12) 0.05472(10) 0.02078(19) Uani d 1 . .
H H23A 0.613539 0.961990 0.098977 0.031 Uiso calc 1 . .
H H23B 0.554014 0.841125 -0.006738 0.031 Uiso calc 1 . .
H H23C 0.771864 0.908668 0.029148 0.031 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'
Br Br -0.2901 2.4595 '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
C7A S1 C2 . . 88.85(4) y
N3 C2 C8 . . 120.14(8) ?
N3 C2 S1 . . 115.73(7) y
C8 C2 S1 . . 124.12(6) ?
C2 N3 C3A . . 110.78(8) y
N3 C3A C4 . . 124.80(8) ?
N3 C3A C7A . . 114.92(8) y
C4 C3A C7A . . 120.23(8) ?
C5 C4 C3A . . 118.40(9) ?
C4 C5 C6 . . 121.12(9) ?
C7 C6 C5 . . 121.06(9) ?
C6 C7 C7A . . 118.06(9) ?
C7 C7A C3A . . 121.11(8) ?
C7 C7A S1 . . 129.11(7) ?
C3A C7A S1 . . 109.69(7) y
C16 C8 C9 . . 119.94(8) ?
C16 C8 C2 . . 119.48(8) ?
C9 C8 C2 . . 120.55(8) ?
N9 C9 O1 . . 121.20(8) ?
N9 C9 C8 . . 120.80(8) ?
O1 C9 C8 . . 118.00(8) ?
C10 O1 C9 . . 121.82(7) y
C9 N9 C17 . . 125.28(8) y
O1 C10 C11 . . 117.00(8) ?
O1 C10 C15 . . 121.11(8) ?
C11 C10 C15 . . 121.89(9) ?
C10 C11 C12 . . 118.90(9) ?
C11 C12 C13 . . 119.52(9) ?
C14 C13 C12 . . 121.77(9) ?
C14 C13 Br1 . . 119.00(7) ?
C12 C13 Br1 . . 119.21(7) ?
C13 C14 C15 . . 119.05(9) ?
C10 C15 C14 . . 118.86(8) ?
C10 C15 C16 . . 118.19(8) ?
C14 C15 C16 . . 122.95(8) ?
C8 C16 C15 . . 120.85(8) ?
C18 C17 C22 . . 119.00(8) ?
C18 C17 N9 . . 116.72(8) ?
C22 C17 N9 . . 123.92(8) ?
C19 C18 C17 . . 120.48(9) ?
C18 C19 C20 . . 121.05(9) ?
C21 C20 C19 . . 117.95(9) ?
C21 C20 C23 . . 121.46(9) ?
C19 C20 C23 . . 120.58(9) ?
C22 C21 C20 . . 121.80(9) ?
C21 C22 C17 . . 119.69(9) ?
C5 C4 H4 . . 120.8 ?
C3A C4 H4 . . 120.8 ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 H7 . . 121.0 ?
C7A C7 H7 . . 121.0 ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C8 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 H19 . . 119.5 ?
C20 C19 H19 . . 119.5 ?
C22 C21 H21 . . 119.1 ?
C20 C21 H21 . . 119.1 ?
C21 C22 H22 . . 120.2 ?
C17 C22 H22 . . 120.2 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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
S1 C7A . 1.7340(9) y
S1 C2 . 1.7512(9) y
C2 N3 . 1.3094(12) y
C2 C8 . 1.4705(12) y
N3 C3A . 1.3809(12) ?
C3A C4 . 1.4055(13) ?
C3A C7A . 1.4082(13) ?
C4 C5 . 1.3849(14) ?
C5 C6 . 1.4085(15) ?
C6 C7 . 1.3872(14) ?
C7 C7A . 1.4015(13) ?
C8 C16 . 1.3600(13) ?
C8 C9 . 1.4616(12) ?
C9 N9 . 1.2708(12) y
C9 O1 . 1.3819(11) y
O1 C10 . 1.3751(12) y
N9 C17 . 1.4127(12) y
C10 C11 . 1.3896(13) ?
C10 C15 . 1.3985(13) ?
C11 C12 . 1.3931(14) ?
C12 C13 . 1.3954(14) ?
C13 C14 . 1.3849(13) ?
C13 Br1 . 1.8969(10) y
C14 C15 . 1.4049(13) ?
C15 C16 . 1.4382(13) ?
C17 C18 . 1.4010(13) ?
C17 C22 . 1.4010(13) ?
C18 C19 . 1.3915(14) ?
C19 C20 . 1.3977(15) ?
C20 C21 . 1.3964(14) ?
C20 C23 . 1.5057(14) ?
C21 C22 . 1.3934(13) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 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
C7 H7 Br1 1_444 0.95 3.11 3.7721(10) 127.9 yes
C22 H22 N3 2_666 0.95 2.63 3.5716(13) 168.8 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
C7A S1 C2 N3 . . . . 0.05(7) ?
C7A S1 C2 C8 . . . . -179.77(8) ?
C8 C2 N3 C3A . . . . 179.03(8) ?
S1 C2 N3 C3A . . . . -0.79(10) ?
C2 N3 C3A C4 . . . . -176.34(9) ?
C2 N3 C3A C7A . . . . 1.36(11) ?
N3 C3A C4 C5 . . . . 177.03(9) ?
C7A C3A C4 C5 . . . . -0.56(14) ?
C3A C4 C5 C6 . . . . 1.09(16) ?
C4 C5 C6 C7 . . . . -0.75(17) ?
C5 C6 C7 C7A . . . . -0.15(16) ?
C6 C7 C7A C3A . . . . 0.68(15) ?
C6 C7 C7A S1 . . . . -175.47(8) ?
N3 C3A C7A C7 . . . . -178.14(9) ?
C4 C3A C7A C7 . . . . -0.33(14) ?
N3 C3A C7A S1 . . . . -1.32(10) ?
C4 C3A C7A S1 . . . . 176.50(7) ?
C2 S1 C7A C7 . . . . 177.19(10) ?
C2 S1 C7A C3A . . . . 0.69(7) ?
N3 C2 C8 C16 . . . . 5.52(13) ?
S1 C2 C8 C16 . . . . -174.66(7) ?
N3 C2 C8 C9 . . . . -172.19(8) ?
S1 C2 C8 C9 . . . . 7.62(12) ?
C16 C8 C9 N9 . . . . -178.29(9) ?
C2 C8 C9 N9 . . . . -0.59(13) ?
C16 C8 C9 O1 . . . . 2.26(13) ?
C2 C8 C9 O1 . . . . 179.97(8) ?
N9 C9 O1 C10 . . . . 176.74(8) ?
C8 C9 O1 C10 . . . . -3.82(12) ?
O1 C9 N9 C17 . . . . -6.20(14) ?
C8 C9 N9 C17 . . . . 174.37(8) ?
C9 O1 C10 C11 . . . . -176.93(8) ?
C9 O1 C10 C15 . . . . 2.96(13) ?
O1 C10 C11 C12 . . . . 179.31(8) ?
C15 C10 C11 C12 . . . . -0.57(14) ?
C10 C11 C12 C13 . . . . -0.22(14) ?
C11 C12 C13 C14 . . . . 0.92(15) ?
C11 C12 C13 Br1 . . . . -177.29(7) ?
C12 C13 C14 C15 . . . . -0.80(14) ?
Br1 C13 C14 C15 . . . . 177.41(7) ?
O1 C10 C15 C14 . . . . -179.19(8) ?
C11 C10 C15 C14 . . . . 0.68(13) ?
O1 C10 C15 C16 . . . . -0.42(13) ?
C11 C10 C15 C16 . . . . 179.46(8) ?
C13 C14 C15 C10 . . . . 0.00(13) ?
C13 C14 C15 C16 . . . . -178.71(9) ?
C9 C8 C16 C15 . . . . 0.14(13) ?
C2 C8 C16 C15 . . . . -177.59(8) ?
C10 C15 C16 C8 . . . . -1.08(13) ?
C14 C15 C16 C8 . . . . 177.64(9) ?
C9 N9 C17 C18 . . . . 145.41(10) ?
C9 N9 C17 C22 . . . . -41.55(14) ?
C22 C17 C18 C19 . . . . 0.84(14) ?
N9 C17 C18 C19 . . . . 174.24(9) ?
C17 C18 C19 C20 . . . . -1.56(15) ?
C18 C19 C20 C21 . . . . 0.79(15) ?
C18 C19 C20 C23 . . . . -179.58(10) ?
C19 C20 C21 C22 . . . . 0.68(15) ?
C23 C20 C21 C22 . . . . -178.95(10) ?
C20 C21 C22 C17 . . . . -1.37(15) ?
C18 C17 C22 C21 . . . . 0.59(14) ?
N9 C17 C22 C21 . . . . -172.29(9) ?
