#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224705.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_2224705
loop_
_publ_author_name
'Loghmani-Khouzani, Hossein'
'Hajiheidari, Dariush'
'Robinson, Ward T.'
'Kia, Reza'
_publ_section_title
;
 2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone
;
_journal_coeditor_code           LH2971
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o209
_journal_paper_doi               10.1107/S1600536809053112
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H10 Br N O3 S2'
_chemical_formula_moiety         'C15 H10 Br N O3 S2'
_chemical_formula_sum            'C15 H10 Br N O3 S2'
_chemical_formula_weight         396.27
_chemical_melting_point          470
_chemical_name_systematic
;
2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.178(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6695(10)
_cell_length_b                   24.489(4)
_cell_length_c                   10.7042(19)
_cell_measurement_reflns_used    3475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.53
_cell_volume                     1482.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6602
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  0.8636
_exptl_absorpt_correction_T_min  0.3634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.835
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0547P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2140
_reflns_number_total             2564
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2971.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1482.2(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224705
_cod_database_fobs_code          2224705
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.73768(6) 0.334681(12) 0.50902(3) 0.02981(14) Uani d . 1 . .
C C6 0.1307(5) 0.72648(11) 0.1923(3) 0.0176(6) Uani d . 1 . .
C C5 0.2796(6) 0.77145(12) 0.2066(3) 0.0254(7) Uani d . 1 . .
H H5A 0.4151 0.7739 0.1630 0.031 Uiso calc R 1 . .
C C4 0.2209(6) 0.81234(12) 0.2872(3) 0.0285(8) Uani d . 1 . .
H H4A 0.3187 0.8427 0.2984 0.034 Uiso calc R 1 . .
C C3 0.0172(6) 0.80883(13) 0.3521(3) 0.0278(8) Uani d . 1 . .
H H3A -0.0167 0.8368 0.4069 0.033 Uiso calc R 1 . .
C C2 -0.1355(6) 0.76516(12) 0.3374(3) 0.0234(7) Uani d . 1 . .
H H2A -0.2719 0.7633 0.3805 0.028 Uiso calc R 1 . .
C C1 -0.0776(5) 0.72389(11) 0.2555(3) 0.0180(6) Uani d . 1 . .
C C7 0.0046(5) 0.64645(11) 0.1287(3) 0.0152(6) Uani d . 1 . .
C C8 0.2422(5) 0.54542(11) 0.1342(3) 0.0161(6) Uani d . 1 . .
H H8A 0.2775 0.5135 0.0852 0.019 Uiso calc R 1 . .
H H8B 0.3830 0.5680 0.1414 0.019 Uiso calc R 1 . .
C C9 0.1874(5) 0.52687(11) 0.2645(3) 0.0187(7) Uani d . 1 . .
C C10 0.3307(5) 0.48088(11) 0.3204(3) 0.0165(6) Uani d . 1 . .
C C15 0.5345(5) 0.46196(11) 0.2724(3) 0.0194(7) Uani d . 1 . .
H H15A 0.5888 0.4782 0.2013 0.023 Uiso calc R 1 . .
C C14 0.6590(5) 0.41889(11) 0.3296(3) 0.0208(7) Uani d . 1 . .
H H14A 0.7975 0.4063 0.2979 0.025 Uiso calc R 1 . .
C C13 0.5753(5) 0.39509(11) 0.4333(3) 0.0202(7) Uani d . 1 . .
C C12 0.3738(6) 0.41345(11) 0.4839(3) 0.0225(7) Uani d . 1 . .
H H12A 0.3209 0.3971 0.5551 0.027 Uiso calc R 1 . .
C C11 0.2519(6) 0.45649(12) 0.4270(3) 0.0226(7) Uani d . 1 . .
H H11A 0.1154 0.4694 0.4603 0.027 Uiso calc R 1 . .
N N1 0.1732(4) 0.68070(9) 0.1198(2) 0.0176(6) Uani d . 1 . .
O O2 0.0855(4) 0.59122(8) -0.07094(18) 0.0240(5) Uani d . 1 . .
O O1 -0.2124(4) 0.55675(8) 0.0658(2) 0.0225(5) Uani d . 1 . .
O O3 0.0318(4) 0.54839(9) 0.3174(2) 0.0296(6) Uani d . 1 . .
S S2 0.01146(13) 0.58258(3) 0.05223(7) 0.01619(19) Uani d . 1 . .
S S1 -0.22406(13) 0.66352(3) 0.21941(7) 0.0196(2) 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
C5 C6 N1 . . 124.8(3) ?
C5 C6 C1 . . 120.5(3) ?
N1 C6 C1 . . 114.6(2) ?
C4 C5 C6 . . 118.2(3) ?
C4 C5 H5A . . 120.9 ?
C6 C5 H5A . . 120.9 ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
C2 C3 C4 . . 121.8(3) ?
C2 C3 H3A . . 119.1 ?
C4 C3 H3A . . 119.1 ?
C3 C2 C1 . . 117.4(3) ?
C3 C2 H2A . . 121.3 ?
C1 C2 H2A . . 121.3 ?
C2 C1 C6 . . 121.0(3) ?
C2 C1 S1 . . 129.1(2) ?
C6 C1 S1 . . 109.8(2) ?
N1 C7 S1 . . 118.6(2) ?
N1 C7 S2 . . 120.2(2) ?
S1 C7 S2 . . 121.18(17) ?
C9 C8 S2 . . 114.5(2) ?
C9 C8 H8A . . 108.6 ?
S2 C8 H8A . . 108.6 ?
C9 C8 H8B . . 108.6 ?
S2 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
O3 C9 C10 . . 122.6(3) ?
O3 C9 C8 . . 120.5(3) ?
C10 C9 C8 . . 116.9(3) ?
C15 C10 C11 . . 119.3(3) ?
C15 C10 C9 . . 123.5(3) ?
C11 C10 C9 . . 117.1(3) ?
C10 C15 C14 . . 120.3(3) ?
C10 C15 H15A . . 119.8 ?
C14 C15 H15A . . 119.8 ?
C13 C14 C15 . . 119.1(3) ?
C13 C14 H14A . . 120.5 ?
C15 C14 H14A . . 120.5 ?
C14 C13 C12 . . 121.8(3) ?
C14 C13 Br1 . . 119.6(2) ?
C12 C13 Br1 . . 118.6(2) ?
C13 C12 C11 . . 118.7(3) ?
C13 C12 H12A . . 120.6 ?
C11 C12 H12A . . 120.6 ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11A . . 119.7 ?
C10 C11 H11A . . 119.7 ?
C7 N1 C6 . . 109.0(3) ?
O2 S2 O1 . . 118.72(13) ?
O2 S2 C7 . . 108.34(13) ?
O1 S2 C7 . . 107.07(13) ?
O2 S2 C8 . . 106.09(13) ?
O1 S2 C8 . . 110.47(13) ?
C7 S2 C8 . . 105.39(13) ?
C1 S1 C7 . . 87.97(14) ?
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
Br1 C13 . 1.893(3) ?
C6 C5 . 1.389(4) ?
C6 N1 . 1.395(4) ?
C6 C1 . 1.404(4) ?
C5 C4 . 1.378(5) ?
C5 H5A . 0.9300 ?
C4 C3 . 1.393(5) ?
C4 H4A . 0.9300 ?
C3 C2 . 1.378(4) ?
C3 H3A . 0.9300 ?
C2 C1 . 1.393(4) ?
C2 H2A . 0.9300 ?
C1 S1 . 1.726(3) ?
C7 N1 . 1.281(4) ?
C7 S1 . 1.726(3) ?
C7 S2 . 1.767(3) ?
C8 C9 . 1.520(4) ?
C8 S2 . 1.773(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O3 . 1.204(4) ?
C9 C10 . 1.489(4) ?
C10 C15 . 1.378(4) ?
C10 C11 . 1.391(4) ?
C15 C14 . 1.386(4) ?
C15 H15A . 0.9300 ?
C14 C13 . 1.369(4) ?
C14 H14A . 0.9300 ?
C13 C12 . 1.375(4) ?
C12 C11 . 1.378(4) ?
C12 H12A . 0.9300 ?
C11 H11A . 0.9300 ?
O2 S2 . 1.428(2) ?
O1 S2 . 1.435(2) ?
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
C4 H4A O2 4_676 0.93 2.56 3.420(4) 154.0 y
C8 H8A O1 3_565 0.97 2.37 3.289(3) 157.7 y
C8 H8B O1 1_655 0.97 2.50 3.241(4) 132.8 y
C14 H14A O2 3_665 0.93 2.56 3.226(4) 128.4 y
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
N1 C6 C5 C4 . . . . -176.3(3) ?
C1 C6 C5 C4 . . . . 2.1(4) ?
C6 C5 C4 C3 . . . . -0.4(4) ?
C5 C4 C3 C2 . . . . -1.0(5) ?
C4 C3 C2 C1 . . . . 0.6(4) ?
C3 C2 C1 C6 . . . . 1.1(4) ?
C3 C2 C1 S1 . . . . 178.0(2) ?
C5 C6 C1 C2 . . . . -2.5(4) ?
N1 C6 C1 C2 . . . . 176.0(3) ?
C5 C6 C1 S1 . . . . -180.0(2) ?
N1 C6 C1 S1 . . . . -1.4(3) ?
S2 C8 C9 O3 . . . . -19.1(4) ?
S2 C8 C9 C10 . . . . 159.8(2) ?
O3 C9 C10 C15 . . . . -168.3(3) ?
C8 C9 C10 C15 . . . . 12.9(4) ?
O3 C9 C10 C11 . . . . 11.5(4) ?
C8 C9 C10 C11 . . . . -167.4(3) ?
C11 C10 C15 C14 . . . . 0.3(4) ?
C9 C10 C15 C14 . . . . 180.0(3) ?
C10 C15 C14 C13 . . . . 0.7(4) ?
C15 C14 C13 C12 . . . . -1.4(5) ?
C15 C14 C13 Br1 . . . . 177.9(2) ?
C14 C13 C12 C11 . . . . 1.0(5) ?
Br1 C13 C12 C11 . . . . -178.3(2) ?
C13 C12 C11 C10 . . . . 0.1(5) ?
C15 C10 C11 C12 . . . . -0.7(4) ?
C9 C10 C11 C12 . . . . 179.6(3) ?
S1 C7 N1 C6 . . . . 1.1(3) ?
S2 C7 N1 C6 . . . . -177.54(19) ?
C5 C6 N1 C7 . . . . 178.7(3) ?
C1 C6 N1 C7 . . . . 0.3(3) ?
N1 C7 S2 O2 . . . . -43.5(3) ?
S1 C7 S2 O2 . . . . 137.99(16) ?
N1 C7 S2 O1 . . . . -172.6(2) ?
S1 C7 S2 O1 . . . . 8.8(2) ?
N1 C7 S2 C8 . . . . 69.7(3) ?
S1 C7 S2 C8 . . . . -108.81(18) ?
C9 C8 S2 O2 . . . . -174.09(19) ?
C9 C8 S2 O1 . . . . -44.2(2) ?
C9 C8 S2 C7 . . . . 71.1(2) ?
C2 C1 S1 C7 . . . . -175.6(3) ?
C6 C1 S1 C7 . . . . 1.6(2) ?
N1 C7 S1 C1 . . . . -1.6(2) ?
S2 C7 S1 C1 . . . . 176.96(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744116
