#------------------------------------------------------------------------------
#$Date: 2021-04-10 08:05:20 +0300 (Sat, 10 Apr 2021) $
#$Revision: 264036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243804.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_2243804
loop_
_publ_author_name
'Mahesha, Ninganayaka'
'Yathirajan, Hemmige S.'
'Nagma Banu, Holalagudu A.'
'Kalluraya, Balakrishna'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 Different patterns of supramolecular aggregation in three amides
 containing N-(benzo[d]thiazolyl) substituents
;
_journal_coeditor_code           HB7974
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              504
_journal_page_last               511
_journal_paper_doi               10.1107/S2056989021003637
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H9 Br N2 O S'
_chemical_formula_moiety         'C14 H9 Br N2 O S'
_chemical_formula_sum            'C14 H9 Br N2 O S'
_chemical_formula_weight         333.19
_chemical_name_systematic
;
N-(Benzo[d]thiazol-6-yl)-3-bromobenzamide
;
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 95.371(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.2210(10)
_cell_length_b                   4.9481(3)
_cell_length_c                   10.9981(6)
_cell_measurement_reflns_used    2805
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.781
_cell_measurement_theta_min      2.534
_cell_volume                     1312.31(12)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.781
_diffrn_reflns_theta_min         2.534
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.283
_exptl_absorpt_correction_T_max  0.769
_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisRed; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.732
_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     175
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0427
_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)+(0.0826P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2170
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7974sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243804
_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   0.291
_shelx_estimated_absorpt_t_max   0.779
_shelxl_version_number           2.014
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 0.82689(14) 0.5633(6) 0.8202(3) 0.0285(7) Uani d 1 . .
C C2 0.86414(13) 0.3673(6) 0.7894(3) 0.0292(7) Uani d 1 . .
H H2 0.8588 0.2773 0.7150 0.035 Uiso calc 1 . .
C C3 0.90946(13) 0.3081(7) 0.8714(3) 0.0300(7) Uani d 1 . .
Br Br3 0.96192(2) 0.05035(8) 0.82512(3) 0.04011(16) Uani d 1 . .
C C4 0.91689(15) 0.4331(7) 0.9832(3) 0.0387(8) Uani d 1 . .
H H4 0.9468 0.3866 1.0383 0.046 Uiso calc 1 . .
C C5 0.88018(16) 0.6257(8) 1.0131(3) 0.0422(9) Uani d 1 . .
H H5 0.8855 0.7119 1.0884 0.051 Uiso calc 1 . .
C C6 0.83486(14) 0.6942(7) 0.9320(3) 0.0375(8) Uani d 1 . .
H H6 0.8101 0.8266 0.9525 0.045 Uiso calc 1 . .
C C11 0.77814(13) 0.6452(7) 0.7322(3) 0.0307(7) Uani d 1 . .
O O11 0.76470(12) 0.8823(5) 0.7208(3) 0.0490(7) Uani d 1 . .
N N11 0.75247(12) 0.4425(6) 0.6688(3) 0.0327(6) Uani d 1 . .
H H11 0.7634(15) 0.274(7) 0.689(3) 0.039 Uiso d 1 . .
S S11 0.55928(5) 0.8448(3) 0.49883(12) 0.0659(4) Uani d 1 . .
C C12 0.53824(18) 0.6976(10) 0.3595(4) 0.0604(12) Uani d 1 . .
H H12 0.5048 0.7447 0.3163 0.072 Uiso calc 1 . .
N N13 0.57051(15) 0.5206(8) 0.3178(3) 0.0594(10) Uani d 1 . .
C C13A 0.61798(16) 0.4886(8) 0.4010(3) 0.0421(9) Uani d 1 . .
C C14 0.66075(17) 0.3153(10) 0.3870(3) 0.0530(11) Uani d 1 . .
H H14 0.6603 0.2073 0.3177 0.064 Uiso calc 1 . .
C C15 0.70478(16) 0.3012(8) 0.4767(3) 0.0455(9) Uani d 1 . .
H H15 0.7336 0.1800 0.4687 0.055 Uiso calc 1 . .
C C16 0.70600(14) 0.4690(7) 0.5795(3) 0.0310(7) Uani d 1 . .
C C17 0.66363(14) 0.6445(7) 0.5954(3) 0.0375(8) Uani d 1 . .
H H17 0.6645 0.7552 0.6639 0.045 Uiso calc 1 . .
C C17A 0.61882(14) 0.6514(8) 0.5046(3) 0.0397(8) Uani 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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 . . 120.2(3) ?
C6 C1 C11 . . 118.6(3) ?
C2 C1 C11 . . 121.2(3) ?
C3 C2 C1 . . 118.8(3) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C4 C3 C2 . . 121.2(3) ?
C4 C3 Br3 . . 120.4(2) ?
C2 C3 Br3 . . 118.4(2) ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.6(3) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
O11 C11 N11 . . 124.0(3) ?
O11 C11 C1 . . 120.6(3) ?
N11 C11 C1 . . 115.4(3) ?
C11 N11 C16 . . 125.9(3) ?
C11 N11 H11 . . 117(2) ?
C16 N11 H11 . . 117(2) ?
C17A S11 C12 . . 88.6(2) ?
N13 C12 S11 . . 117.6(3) ?
N13 C12 H12 . . 121.2 ?
S11 C12 H12 . . 121.2 ?
C12 N13 C13A . . 109.3(4) ?
C14 C13A C17A . . 120.1(3) ?
C14 C13A N13 . . 125.4(4) ?
C17A C13A N13 . . 114.5(4) ?
C13A C14 C15 . . 119.6(4) ?
C13A C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.1(3) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C17 C16 C15 . . 121.4(3) ?
C17 C16 N11 . . 121.5(3) ?
C15 C16 N11 . . 117.1(3) ?
C16 C17 C17A . . 117.6(3) ?
C16 C17 H17 . . 121.2 ?
C17A C17 H17 . . 121.2 ?
C13A C17A C17 . . 121.2(3) ?
C13A C17A S11 . . 110.0(3) ?
C17 C17A S11 . . 128.8(3) ?
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 C6 . 1.387(4) ?
C1 C2 . 1.388(5) ?
C1 C11 . 1.510(4) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(5) ?
C3 Br3 . 1.903(3) ?
C4 C5 . 1.364(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C11 O11 . 1.221(4) ?
C11 N11 . 1.341(4) ?
N11 C16 . 1.429(4) ?
N11 H11 . 0.90(4) ?
S11 C17A . 1.727(4) ?
S11 C12 . 1.730(5) ?
C12 N13 . 1.287(6) ?
C12 H12 . 0.9300 ?
N13 C13A . 1.410(5) ?
C13A C14 . 1.365(6) ?
C13A C17A . 1.394(5) ?
C14 C15 . 1.385(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.400(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.368(5) ?
C17 C17A . 1.405(4) ?
C17 H17 . 0.9300 ?
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
N11 H11 O11 1_545 0.90(4) 1.97(3) 2.840(4) 164(3) no
C12 H12 N13 2_655 0.93 2.62 3.512(6) 161 no
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
C6 C1 C2 C3 . . . . -0.8(5) ?
C11 C1 C2 C3 . . . . 177.2(3) ?
C1 C2 C3 C4 . . . . 2.2(5) ?
C1 C2 C3 Br3 . . . . -177.3(2) ?
C2 C3 C4 C5 . . . . -2.2(5) ?
Br3 C3 C4 C5 . . . . 177.3(3) ?
C3 C4 C5 C6 . . . . 0.8(6) ?
C2 C1 C6 C5 . . . . -0.5(5) ?
C11 C1 C6 C5 . . . . -178.6(3) ?
C4 C5 C6 C1 . . . . 0.5(6) ?
C6 C1 C11 O11 . . . . 39.0(5) ?
C2 C1 C11 O11 . . . . -139.0(4) ?
C6 C1 C11 N11 . . . . -141.9(3) ?
C2 C1 C11 N11 . . . . 40.0(4) ?
O11 C11 N11 C16 . . . . -0.2(6) ?
C1 C11 N11 C16 . . . . -179.2(3) ?
C17A S11 C12 N13 . . . . 0.3(4) ?
S11 C12 N13 C13A . . . . 0.0(6) ?
C12 N13 C13A C14 . . . . 179.3(4) ?
C12 N13 C13A C17A . . . . -0.3(6) ?
C17A C13A C14 C15 . . . . 0.4(7) ?
N13 C13A C14 C15 . . . . -179.2(4) ?
C13A C14 C15 C16 . . . . -1.7(7) ?
C14 C15 C16 C17 . . . . 1.6(6) ?
C14 C15 C16 N11 . . . . 179.6(4) ?
C11 N11 C16 C17 . . . . -39.9(5) ?
C11 N11 C16 C15 . . . . 142.2(4) ?
C15 C16 C17 C17A . . . . -0.3(6) ?
N11 C16 C17 C17A . . . . -178.1(3) ?
C14 C13A C17A C17 . . . . 1.0(6) ?
N13 C13A C17A C17 . . . . -179.4(4) ?
C14 C13A C17A S11 . . . . -179.1(3) ?
N13 C13A C17A S11 . . . . 0.6(5) ?
C16 C17 C17A C13A . . . . -1.0(6) ?
C16 C17 C17A S11 . . . . 179.0(3) ?
C12 S11 C17A C13A . . . . -0.5(3) ?
C12 S11 C17A C17 . . . . 179.5(4) ?

_cod_database_fobs_code 2243804
