#------------------------------------------------------------------------------
#$Date: 2015-07-05 10:48:00 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140072 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/32/4513262.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4513262
loop_
_publ_author_name
'Eccles, Kevin S.'
'Morrison, Robin E.'
'Sinha, Abhijeet S.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Investigating C═S···I Halogen Bonding for
 Cocrystallization with Primary Thioamides
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3442
_journal_paper_doi               10.1021/acs.cgd.5b00513
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C6 F4 I2, 2(C7 H6 Cl N S)'
_chemical_formula_sum            'C20 H12 Cl2 F4 I2 N2 S2'
_chemical_formula_weight         745.16
_chemical_name_common
;             
4-chlorothiobenzamide & 
1,4 diiodotetrafluorobenzene (2:1) cocrystal
;
_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'
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.790(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0308(17)
_cell_length_b                   9.2912(11)
_cell_length_c                   11.6550(16)
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      22.7975
_cell_measurement_theta_min      2.8227
_cell_volume                     1240.5(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection
;
Bruker Instrument Service v2009, 3, 0, 0
;
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11553
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    2.961
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.509
_refine_ls_extinction_coef       0.0108(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0289
_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)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                1785
_reflns_number_total             2181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00513_si_002.cif
_cod_data_source_block           17_2.1
_cod_depositor_comments
'Adding full bibliography for 4513250--4513263.cif.'
_cod_database_code               4513262
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_refinement_flags
_atom_site_occupancy
C C1 0.3074(4) 0.6090(5) 0.0199(4) 0.0394(10) Uani d . 1
C C2 0.2679(4) 0.5180(5) -0.0789(4) 0.0425(11) Uani d . 1
H H2 0.2113 0.5499 -0.1479 0.051 Uiso calc R 1
C C3 0.3124(5) 0.3809(5) -0.0749(4) 0.0512(13) Uani d . 1
H H3 0.2857 0.32 -0.1409 0.061 Uiso calc R 1
C C4 0.3965(5) 0.3345(5) 0.0271(5) 0.0522(14) Uani d . 1
C C5 0.4358(5) 0.4219(6) 0.1262(5) 0.0592(14) Uani d . 1
H H5 0.492 0.389 0.1952 0.071 Uiso calc R 1
C C6 0.3909(4) 0.5589(5) 0.1224(4) 0.0514(13) Uani d . 1
H H6 0.417 0.6184 0.1895 0.062 Uiso calc R 1
C C7 0.2604(4) 0.7585(5) 0.0166(4) 0.0400(11) Uani d . 1
S S8 0.25405(14) 0.84280(12) 0.14052(11) 0.0529(4) Uani d . 1
H H9A 0.204(5) 0.908(3) -0.095(5) 0.073(19) Uiso d D 1
H H9B 0.245(5) 0.786(6) -0.146(5) 0.072(19) Uiso d . 1
N N9 0.2242(5) 0.8203(5) -0.0903(4) 0.0584(13) Uani d D 1
Cl Cl10 0.45212(17) 0.16107(14) 0.0320(2) 0.0830(5) Uani d . 1
C C11 0.0513(4) 0.3619(4) 0.0283(4) 0.0387(10) Uani d . 1
C C12 -0.0058(4) 0.4037(5) -0.0888(4) 0.0399(11) Uani d . 1
C C13 0.0548(4) 0.4629(5) 0.1162(4) 0.0389(10) Uani d . 1
I I14 0.12666(3) 0.15782(3) 0.06918(3) 0.04510(18) Uani d . 1
F F15 -0.0101(3) 0.3118(3) -0.1809(2) 0.0568(8) Uani d . 1
F F16 0.1096(3) 0.4308(3) 0.2338(2) 0.0600(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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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
C6 C1 C2 . . 119.0(4)
C6 C1 C7 . . 120.2(4)
C2 C1 C7 . . 120.8(4)
C3 C2 C1 . . 120.2(4)
C3 C2 H2 . . 119.9
C1 C2 H2 . . 119.9
C4 C3 C2 . . 119.7(5)
C4 C3 H3 . . 120.2
C2 C3 H3 . . 120.2
C5 C4 C3 . . 121.1(4)
C5 C4 Cl10 . . 119.4(4)
C3 C4 Cl10 . . 119.6(4)
C4 C5 C6 . . 119.3(5)
C4 C5 H5 . . 120.4
C6 C5 H5 . . 120.4
C5 C6 C1 . . 120.7(5)
C5 C6 H6 . . 119.6
C1 C6 H6 . . 119.6
N9 C7 C1 . . 116.2(4)
N9 C7 S8 . . 121.7(4)
C1 C7 S8 . . 122.1(3)
C7 N9 H9A . . 119.(4)
C7 N9 H9B . . 119.(4)
H9A N9 H9B . . 118.(5)
C13 C11 C12 . . 115.8(4)
C13 C11 I14 . . 122.3(3)
C12 C11 I14 . . 121.9(3)
F15 C12 C13 . 3_565 118.4(4)
F15 C12 C11 . . 119.4(4)
C13 C12 C11 3_565 . 122.2(4)
F16 C13 C12 . 3_565 118.4(4)
F16 C13 C11 . . 119.6(4)
C12 C13 C11 3_565 . 122.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.386(6)
C1 C2 . 1.389(6)
C1 C7 . 1.496(6)
C2 C3 . 1.377(7)
C2 H2 . 0.93
C3 C4 . 1.374(8)
C3 H3 . 0.93
C4 C5 . 1.372(7)
C4 Cl10 . 1.739(5)
C5 C6 . 1.378(7)
C5 H5 . 0.93
C6 H6 . 0.93
C7 N9 . 1.319(6)
C7 S8 . 1.666(4)
N9 H9A . 0.85(2)
N9 H9B . 0.83(6)
C11 C13 . 1.380(6)
C11 C12 . 1.384(6)
C11 I14 . 2.093(4)
C12 F15 . 1.360(5)
C12 C13 3_565 1.368(6)
C13 F16 . 1.360(5)
C13 C12 3_565 1.368(6)
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
N9 H9A F16 4_575 0.85(2) 2.47(4) 3.118(5) 133.(5)
N9 H9B S8 4_575 0.83(6) 2.79(6) 3.599(5) 166.(5)
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_4
_geom_torsion
C6 C1 C2 C3 . -0.8(7)
C7 C1 C2 C3 . 179.7(4)
C1 C2 C3 C4 . -0.3(7)
C2 C3 C4 C5 . 1.1(8)
C2 C3 C4 Cl10 . 179.8(4)
C3 C4 C5 C6 . -0.8(8)
Cl10 C4 C5 C6 . -179.5(4)
C4 C5 C6 C1 . -0.3(8)
C2 C1 C6 C5 . 1.1(7)
C7 C1 C6 C5 . -179.4(5)
C6 C1 C7 N9 . 151.6(5)
C2 C1 C7 N9 . -28.9(7)
C6 C1 C7 S8 . -28.3(6)
C2 C1 C7 S8 . 151.2(4)
C13 C11 C12 F15 . 178.2(4)
I14 C11 C12 F15 . -2.1(6)
C13 C11 C12 C13 3_565 0.6(7)
I14 C11 C12 C13 3_565 -179.7(3)
C12 C11 C13 F16 . -179.7(4)
I14 C11 C13 F16 . 0.6(6)
C12 C11 C13 C12 3_565 -0.6(7)
I14 C11 C13 C12 3_565 179.7(3)
