#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/33/2233303.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_2233303
loop_
_publ_author_name
'Wang, Dao-Cai'
'Song, Hang'
'Yang, Chang'
'Huang, Wen-Cai'
'Yao, Shun'
_publ_section_title
;
 2-Chloro-N-(4-chloro-3-iodophenyl)-4-(methylsulfonyl)benzamide
;
_journal_coeditor_code           TK5034
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o189
_journal_paper_doi               10.1107/S1600536811053633
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H10 Cl2 I N O3 S'
_chemical_formula_moiety         'C14 H10 Cl2 I N O3 S'
_chemical_formula_sum            'C14 H10 Cl2 I N O3 S'
_chemical_formula_weight         470.09
_chemical_name_systematic
;
2-Chloro-N-(4-chloro-3-iodophenyl)-4-(methylsulfonyl)benzamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.862(5)
_cell_angle_beta                 96.452(5)
_cell_angle_gamma                114.949(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8694(6)
_cell_length_b                   10.3837(8)
_cell_length_c                   10.4288(5)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    290(4)
_cell_measurement_theta_max      26.3221
_cell_measurement_theta_min      2.9082
_cell_volume                     820.25(11)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(4)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6770
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.549
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0284
_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)+(0.0257P)²+0.4057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                2957
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5034.cif
_cod_data_source_block           I
_cod_original_cell_volume        820.25(9)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               2233303
_cod_database_fobs_code          2233303
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I I1 0.61447(3) 0.68561(3) 0.77089(2) 0.04648(9) Uani d . 1 1
Cl Cl1 0.29725(14) 0.32782(12) 0.59427(9) 0.0627(3) Uani d . 1 1
Cl Cl2 0.29306(15) 0.99624(11) 1.34350(10) 0.0603(3) Uani d . 1 1
S S2 0.11153(10) 0.80692(9) 1.76536(8) 0.03759(19) Uani d . 1 1
O O1 0.4697(3) 0.8156(3) 1.2278(2) 0.0620(8) Uani d . 1 1
O O2 0.0367(3) 0.6656(3) 1.7893(2) 0.0536(7) Uani d . 1 1
O O3 0.0121(4) 0.8840(4) 1.7587(3) 0.0676(8) Uani d . 1 1
N N1 0.2439(3) 0.5816(3) 1.1495(2) 0.0344(6) Uani d . 1 1
H H1 0.1576 0.5214 1.1721 0.041 Uiso calc R 1 1
C C1 0.4083(4) 0.5502(4) 0.8367(3) 0.0328(7) Uani d . 1 1
C C2 0.2898(4) 0.4068(4) 0.7585(3) 0.0390(8) Uani d . 1 1
C C3 0.1603(4) 0.3219(4) 0.8106(3) 0.0478(9) Uani d . 1 1
H H3 0.0821 0.2240 0.7588 0.057 Uiso calc R 1 1
C C4 0.1467(4) 0.3817(4) 0.9391(3) 0.0412(8) Uani d . 1 1
H H4 0.0578 0.3246 0.9729 0.049 Uiso calc R 1 1
C C5 0.2643(4) 0.5261(3) 1.0182(3) 0.0303(6) Uani d . 1 1
C C6 0.3978(4) 0.6101(3) 0.9675(3) 0.0326(7) Uani d . 1 1
H H6 0.4798 0.7061 1.0210 0.039 Uiso calc R 1 1
C C7 0.3431(4) 0.7173(4) 1.2433(3) 0.0370(7) Uani d . 1 1
C C8 0.2843(4) 0.7407(3) 1.3728(3) 0.0315(7) Uani d . 1 1
C C9 0.2612(4) 0.8646(3) 1.4266(3) 0.0346(7) Uani d . 1 1
C C10 0.2081(4) 0.8860(3) 1.5459(3) 0.0346(7) Uani d . 1 1
H H10 0.1917 0.9691 1.5806 0.042 Uiso calc R 1 1
C C11 0.1800(3) 0.7808(3) 1.6127(3) 0.0307(6) Uani d . 1 1
C C12 0.2046(4) 0.6571(3) 1.5633(3) 0.0332(7) Uani d . 1 1
H H12 0.1865 0.5880 1.6099 0.040 Uiso calc R 1 1
C C13 0.2566(4) 0.6382(4) 1.4433(3) 0.0336(7) Uani d . 1 1
H H13 0.2734 0.5553 1.4090 0.040 Uiso calc R 1 1
C C14 0.3027(5) 0.9225(5) 1.8925(3) 0.0601(11) Uani d . 1 1
H H14A 0.2762 0.9474 1.9789 0.090 Uiso calc R 1 1
H H14B 0.3667 1.0126 1.8717 0.090 Uiso calc R 1 1
H H14C 0.3697 0.8705 1.8963 0.090 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
O2 S2 C11 107.98(15)
O2 S2 C14 106.74(19)
O3 S2 O2 118.76(18)
O3 S2 C11 108.53(16)
O3 S2 C14 109.7(2)
C14 S2 C11 104.21(16)
C5 N1 H1 116.0
C7 N1 H1 116.0
C7 N1 C5 128.0(2)
C2 C1 I1 123.1(2)
C2 C1 C6 120.3(3)
C6 C1 I1 116.6(2)
C1 C2 Cl1 121.8(2)
C1 C2 C3 119.8(3)
C3 C2 Cl1 118.3(3)
C2 C3 H3 119.9
C4 C3 C2 120.3(3)
C4 C3 H3 119.9
C3 C4 H4 119.8
C3 C4 C5 120.4(3)
C5 C4 H4 119.8
C4 C5 N1 117.9(3)
C4 C5 C6 119.4(3)
C6 C5 N1 122.7(3)
C1 C6 C5 119.8(3)
C1 C6 H6 120.1
C5 C6 H6 120.1
O1 C7 N1 124.5(3)
O1 C7 C8 121.2(3)
N1 C7 C8 114.3(2)
C9 C8 C7 121.8(3)
C9 C8 C13 118.5(3)
C13 C8 C7 119.7(3)
C8 C9 Cl2 120.7(2)
C10 C9 Cl2 117.7(3)
C10 C9 C8 121.6(3)
C9 C10 H10 120.8
C9 C10 C11 118.4(3)
C11 C10 H10 120.8
C10 C11 S2 118.7(2)
C12 C11 S2 119.6(2)
C12 C11 C10 121.7(3)
C11 C12 H12 120.7
C11 C12 C13 118.6(3)
C13 C12 H12 120.7
C8 C13 H13 119.4
C12 C13 C8 121.3(3)
C12 C13 H13 119.4
S2 C14 H14A 109.5
S2 C14 H14B 109.5
S2 C14 H14C 109.5
H14A C14 H14B 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
I1 C1 2.090(3)
Cl1 C2 1.735(3)
Cl2 C9 1.731(3)
S2 O2 1.431(3)
S2 O3 1.426(3)
S2 C11 1.769(3)
S2 C14 1.757(4)
O1 C7 1.218(4)
N1 H1 0.8600
N1 C5 1.416(4)
N1 C7 1.348(4)
C1 C2 1.375(5)
C1 C6 1.388(4)
C2 C3 1.381(5)
C3 H3 0.9300
C3 C4 1.378(4)
C4 H4 0.9300
C4 C5 1.382(4)
C5 C6 1.391(4)
C6 H6 0.9300
C7 C8 1.504(4)
C8 C9 1.384(4)
C8 C13 1.388(4)
C9 C10 1.381(4)
C10 H10 0.9300
C10 C11 1.383(4)
C11 C12 1.380(4)
C12 H12 0.9300
C12 C13 1.381(4)
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
N1 H1 O2 2_568 0.86 2.15 2.991(3) 167
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
I1 C1 C2 Cl1 -2.5(4)
I1 C1 C2 C3 177.7(3)
I1 C1 C6 C5 -179.8(2)
Cl1 C2 C3 C4 -178.1(3)
Cl2 C9 C10 C11 179.2(2)
S2 C11 C12 C13 179.4(2)
O1 C7 C8 C9 51.1(5)
O1 C7 C8 C13 -127.0(4)
O2 S2 C11 C10 160.6(2)
O2 S2 C11 C12 -19.6(3)
O3 S2 C11 C10 30.7(3)
O3 S2 C11 C12 -149.6(3)
N1 C5 C6 C1 -178.5(3)
N1 C7 C8 C9 -128.4(3)
N1 C7 C8 C13 53.5(4)
C1 C2 C3 C4 1.8(6)
C2 C1 C6 C5 -1.7(5)
C2 C3 C4 C5 -1.3(6)
C3 C4 C5 N1 -180.0(3)
C3 C4 C5 C6 -0.7(5)
C4 C5 C6 C1 2.2(5)
C5 N1 C7 O1 0.1(6)
C5 N1 C7 C8 179.6(3)
C6 C1 C2 Cl1 179.6(2)
C6 C1 C2 C3 -0.2(5)
C7 N1 C5 C4 179.5(3)
C7 N1 C5 C6 0.2(5)
C7 C8 C9 Cl2 2.0(4)
C7 C8 C9 C10 -179.6(3)
C7 C8 C13 C12 179.2(3)
C8 C9 C10 C11 0.8(5)
C9 C8 C13 C12 1.0(4)
C9 C10 C11 S2 -179.9(2)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 C13 -0.8(4)
C11 C12 C13 C8 0.1(4)
C13 C8 C9 Cl2 -179.8(2)
C13 C8 C9 C10 -1.5(4)
C14 S2 C11 C10 -86.2(3)
C14 S2 C11 C12 93.6(3)
