#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/67/2236748.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_2236748
loop_
_publ_author_name
'Babar, Ayesha'
'Munawar, Munawar Ali'
'Tahir, M. Nawaz'
'Ullah, Fateh'
'Tariq, Muhammad Ilyas'
_publ_section_title
;
 N-(2,4-Dichlorophenyl)-1,3-thiazol-2-amine
;
_journal_coeditor_code           YK2069
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2704
_journal_paper_doi               10.1107/S1600536812035301
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H6 Cl2 N2 S'
_chemical_formula_moiety         'C9 H6 Cl2 N2 S'
_chemical_formula_sum            'C9 H6 Cl2 N2 S'
_chemical_formula_weight         245.12
_chemical_name_systematic
;
N-(2,4-Dichlorophenyl)-1,3-thiazol-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 91.974(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0270(9)
_cell_length_b                   10.1183(6)
_cell_length_c                   7.7159(5)
_cell_measurement_reflns_used    912
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      1.56
_cell_volume                     1016.44(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.80
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8039
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.303
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0286
_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)+(0.0406P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                1957
_reflns_number_total             2245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yk2069.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236748
_cod_database_fobs_code          2236748
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
Cl Cl1 0.24571(4) 0.37457(5) 0.29544(6) 0.0545(2) Uani 1.000 -16
Cl Cl2 -0.05984(3) 0.34681(6) 0.74042(8) 0.0662(2) Uani 1.000 -16
S S1 0.33053(3) 0.77775(4) 0.66934(5) 0.04050(10) Uani 1.000 -16
N N1 0.35990(10) 0.51946(12) 0.57795(18) 0.0403(4) Uani 1.000 -16
N N2 0.49723(10) 0.66580(13) 0.57830(18) 0.0400(4) Uani 1.000 -16
C C1 0.26014(11) 0.48156(14) 0.6171(2) 0.0353(4) Uani 1.000 -16
C C2 0.19932(12) 0.41107(15) 0.4977(2) 0.0369(4) Uani 1.000 -16
C C3 0.10147(12) 0.36979(16) 0.5348(2) 0.0434(5) Uani 1.000 -16
C C4 0.06296(12) 0.40070(17) 0.6935(2) 0.0451(5) Uani 1.000 -16
C C5 0.12029(14) 0.47052(18) 0.8147(2) 0.0505(6) Uani 1.000 -16
C C6 0.21843(14) 0.50928(18) 0.7763(2) 0.0463(5) Uani 1.000 -16
C C7 0.40145(11) 0.64084(14) 0.60680(18) 0.0326(4) Uani 1.000 -16
C C8 0.43848(14) 0.87355(15) 0.6496(2) 0.0455(5) Uani 1.000 -16
C C9 0.51714(14) 0.79861(16) 0.6017(2) 0.0462(5) Uani 1.000 -16
H H1 0.39818 0.46092 0.53165 0.0483 Uiso 1.000 -16
H H3 0.06225 0.32185 0.45384 0.0520 Uiso 1.000 -16
H H5 0.09331 0.49142 0.92130 0.0606 Uiso 1.000 -16
H H6 0.25772 0.55521 0.85926 0.0556 Uiso 1.000 -16
H H8 0.44170 0.96415 0.66933 0.0545 Uiso 1.000 -16
H H9 0.58188 0.83417 0.58503 0.0554 Uiso 1.000 -16
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'
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
_geom_angle_publ_flag
C7 S1 C8 88.89(7) no
C1 N1 C7 125.53(13) no
C7 N2 C9 110.16(13) no
C7 N1 H1 117.00 no
C1 N1 H1 117.00 no
N1 C1 C6 122.05(14) no
N1 C1 C2 120.67(14) no
C2 C1 C6 117.26(14) no
C1 C2 C3 121.78(14) no
Cl1 C2 C3 118.39(12) no
Cl1 C2 C1 119.83(12) no
C2 C3 C4 118.92(15) no
C3 C4 C5 121.14(15) no
Cl2 C4 C3 118.70(12) no
Cl2 C4 C5 120.15(13) no
C4 C5 C6 119.13(15) no
C1 C6 C5 121.76(15) no
S1 C7 N2 114.44(11) no
S1 C7 N1 123.54(11) no
N1 C7 N2 121.87(13) no
S1 C8 C9 109.99(12) no
N2 C9 C8 116.50(16) no
C2 C3 H3 121.00 no
C4 C3 H3 121.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C1 C6 H6 119.00 no
C5 C6 H6 119.00 no
S1 C8 H8 125.00 no
C9 C8 H8 125.00 no
N2 C9 H9 122.00 no
C8 C9 H9 122.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.7327(16) no
Cl2 C4 1.7399(16) no
S1 C7 1.7425(15) no
S1 C8 1.7191(18) no
N1 C1 1.3979(19) no
N1 C7 1.3574(19) no
N2 C7 1.2992(19) no
N2 C9 1.379(2) no
N1 H1 0.8600 no
C1 C6 1.389(2) no
C1 C2 1.391(2) no
C2 C3 1.381(2) no
C3 C4 1.375(2) no
C4 C5 1.372(2) no
C5 C6 1.379(3) no
C8 C9 1.337(2) no
C3 H3 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C8 H8 0.9300 no
C9 H9 0.9300 no
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
N1 H1 N2 3_666 0.86 2.07 2.9302(19) 174 yes
C3 H3 Cl2 4_554 0.93 2.82 3.7483(17) 173 yes
C6 H6 S1 . 0.93 2.87 3.2056(19) 103 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
_geom_torsion_publ_flag
C8 S1 C7 N1 -174.25(13) no
C8 S1 C7 N2 1.39(12) no
C7 S1 C8 C9 -0.80(12) no
C7 N1 C1 C2 134.53(16) no
C7 N1 C1 C6 -47.0(2) no
C1 N1 C7 S1 -9.7(2) no
C1 N1 C7 N2 174.96(14) no
C9 N2 C7 S1 -1.53(17) no
C9 N2 C7 N1 174.19(14) no
C7 N2 C9 C8 0.9(2) no
N1 C1 C2 Cl1 -2.2(2) no
N1 C1 C2 C3 178.44(14) no
C6 C1 C2 Cl1 179.25(12) no
C6 C1 C2 C3 -0.1(2) no
N1 C1 C6 C5 -179.38(15) no
C2 C1 C6 C5 -0.9(2) no
Cl1 C2 C3 C4 -178.59(13) no
C1 C2 C3 C4 0.8(2) no
C2 C3 C4 Cl2 -179.29(12) no
C2 C3 C4 C5 -0.5(3) no
Cl2 C4 C5 C6 178.34(14) no
C3 C4 C5 C6 -0.5(3) no
C4 C5 C6 C1 1.2(3) no
S1 C8 C9 N2 0.13(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658189
