#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237509.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_2237509
loop_
_publ_author_name
'Yousuf, Sammer'
'Shah, Shazia'
'Ambreen, Nida'
'Khan, Khalid M.'
'Ahmad, Shakil'
_publ_section_title
;
 5-Chloro-2-(4-methoxyphenyl)-1,3-benzothiazole
;
_journal_coeditor_code           IS5237
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o360
_journal_paper_doi               10.1107/S1600536813001955
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H10 Cl N O S'
_chemical_formula_moiety         'C14 H10 Cl N O S'
_chemical_formula_sum            'C14 H10 Cl N O S'
_chemical_formula_weight         275.74
_chemical_name_systematic
;
5-Chloro-2-(4-methoxyphenyl)-1,3-benzothiazole
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.0274(16)
_cell_length_b                   14.5512(8)
_cell_length_c                   5.8686(3)
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.53
_cell_volume                     2478.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1996) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13397
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Colorles
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0761
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0983P)²+3.3682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2081
_reflns_number_gt                1965
_reflns_number_total             2299
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5237.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2n 2ab '
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               2237509
_cod_database_fobs_code          2237509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_symmetry_multiplicity
Cl Cl1 0.04504(4) 0.17240(11) -0.0360(2) 0.0787(5) Uani d . 1 1
S S1 0.21904(4) 0.08514(7) 0.52664(16) 0.0494(4) Uani d . 1 1
O O1 0.43838(11) 0.1057(2) 0.1916(6) 0.0656(9) Uani d . 1 1
N N1 0.21907(12) 0.1613(2) 0.1301(5) 0.0437(8) Uani d . 1 1
C C1 0.16642(15) 0.1048(2) 0.4009(6) 0.0450(9) Uani d . 1 1
C C2 0.12234(17) 0.0857(3) 0.4807(7) 0.0502(10) Uani d . 1 1
H H2A 0.1179 0.0592 0.6231 0.060 Uiso calc R 1 1
C C3 0.08560(16) 0.1072(3) 0.3433(7) 0.0556(11) Uani d . 1 1
H H3A 0.0558 0.0946 0.3927 0.067 Uiso calc R 1 1
C C4 0.09246(15) 0.1475(3) 0.1304(8) 0.0530(10) Uani d . 1 1
C C5 0.13595(15) 0.1688(3) 0.0488(7) 0.0471(9) Uani d . 1 1
H H5A 0.1400 0.1968 -0.0922 0.057 Uiso calc R 1 1
C C6 0.17346(14) 0.1466(2) 0.1872(6) 0.0420(9) Uani d . 1 1
C C7 0.24620(14) 0.1318(2) 0.2888(6) 0.0409(9) Uani d . 1 1
C C8 0.29667(14) 0.1305(2) 0.2692(6) 0.0420(9) Uani d . 1 1
C C9 0.32493(16) 0.0941(3) 0.4380(7) 0.0511(10) Uani d . 1 1
H H9A 0.3118 0.0730 0.5727 0.061 Uiso calc R 1 1
C C10 0.37175(16) 0.0885(3) 0.4104(7) 0.0535(11) Uani d . 1 1
H H10A 0.3901 0.0646 0.5261 0.064 Uiso calc R 1 1
C C11 0.39169(15) 0.1187(3) 0.2077(7) 0.0487(10) Uani d . 1 1
C C12 0.36468(15) 0.1576(3) 0.0376(7) 0.0479(9) Uani d . 1 1
H H12A 0.3780 0.1795 -0.0959 0.057 Uiso calc R 1 1
C C13 0.31762(15) 0.1631(2) 0.0709(7) 0.0461(9) Uani d . 1 1
H H13A 0.2994 0.1893 -0.0421 0.055 Uiso calc R 1 1
C C14 0.46063(17) 0.1316(4) -0.0114(9) 0.0717(14) Uani d . 1 1
H H14A 0.4926 0.1149 -0.0032 0.108 Uiso calc R 1 1
H H14B 0.4580 0.1969 -0.0316 0.108 Uiso calc R 1 1
H H14C 0.4465 0.1007 -0.1379 0.108 Uiso calc R 1 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'
Cl Cl 0.1484 0.1585 '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
C1 S1 C7 89.62(18)
C11 O1 C14 118.4(4)
C7 N1 C6 110.9(3)
C2 C1 C6 121.3(4)
C2 C1 S1 129.8(3)
C6 C1 S1 109.0(3)
C3 C2 C1 118.2(4)
C3 C2 H2A 120.9
C1 C2 H2A 120.9
C2 C3 C4 120.7(4)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C5 C4 C3 122.3(4)
C5 C4 Cl1 118.9(3)
C3 C4 Cl1 118.8(3)
C4 C5 C6 117.2(4)
C4 C5 H5A 121.4
C6 C5 H5A 121.4
N1 C6 C5 124.7(3)
N1 C6 C1 114.9(4)
C5 C6 C1 120.3(4)
N1 C7 C8 123.7(3)
N1 C7 S1 115.5(3)
C8 C7 S1 120.6(3)
C9 C8 C13 117.8(4)
C9 C8 C7 122.5(4)
C13 C8 C7 119.7(3)
C10 C9 C8 121.5(4)
C10 C9 H9A 119.2
C8 C9 H9A 119.2
C9 C10 C11 119.6(4)
C9 C10 H10A 120.2
C11 C10 H10A 120.2
O1 C11 C12 124.4(4)
O1 C11 C10 115.2(4)
C12 C11 C10 120.5(4)
C13 C12 C11 118.7(4)
C13 C12 H12A 120.7
C11 C12 H12A 120.7
C12 C13 C8 121.9(4)
C12 C13 H13A 119.0
C8 C13 H13A 119.0
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.726(5)
S1 C1 1.720(4)
S1 C7 1.741(4)
O1 C11 1.372(5)
O1 C14 1.407(5)
N1 C7 1.293(5)
N1 C6 1.382(5)
C1 C2 1.391(6)
C1 C6 1.409(5)
C2 C3 1.373(7)
C2 H2A 0.9300
C3 C4 1.394(6)
C3 H3A 0.9300
C4 C5 1.386(6)
C5 C6 1.396(6)
C5 H5A 0.9300
C7 C8 1.470(6)
C8 C9 1.391(5)
C8 C13 1.396(5)
C9 C10 1.371(7)
C9 H9A 0.9300
C10 C11 1.394(6)
C10 H10A 0.9300
C11 C12 1.390(5)
C12 C13 1.382(6)
C12 H12A 0.9300
C13 H13A 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C7 S1 C1 C2 179.4(4)
C7 S1 C1 C6 -0.7(3)
C6 C1 C2 C3 1.2(6)
S1 C1 C2 C3 -178.9(3)
C1 C2 C3 C4 -0.4(6)
C2 C3 C4 C5 -0.9(6)
C2 C3 C4 Cl1 179.6(3)
C3 C4 C5 C6 1.3(6)
Cl1 C4 C5 C6 -179.2(3)
C7 N1 C6 C5 -178.4(3)
C7 N1 C6 C1 0.7(4)
C4 C5 C6 N1 178.6(3)
C4 C5 C6 C1 -0.4(5)
C2 C1 C6 N1 -179.9(3)
S1 C1 C6 N1 0.2(4)
C2 C1 C6 C5 -0.8(5)
S1 C1 C6 C5 179.3(3)
C6 N1 C7 C8 174.5(3)
C6 N1 C7 S1 -1.2(4)
C1 S1 C7 N1 1.1(3)
C1 S1 C7 C8 -174.8(3)
N1 C7 C8 C9 -176.7(3)
S1 C7 C8 C9 -1.1(5)
N1 C7 C8 C13 0.5(5)
S1 C7 C8 C13 176.0(3)
C13 C8 C9 C10 -1.2(6)
C7 C8 C9 C10 176.0(4)
C8 C9 C10 C11 -0.9(6)
C14 O1 C11 C12 -1.3(6)
C14 O1 C11 C10 177.8(4)
C9 C10 C11 O1 -176.6(4)
C9 C10 C11 C12 2.5(6)
O1 C11 C12 C13 177.1(4)
C10 C11 C12 C13 -1.9(6)
C11 C12 C13 C8 -0.2(6)
C9 C8 C13 C12 1.8(5)
C7 C8 C13 C12 -175.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29366670
