#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/32/4513252.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_4513252
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(C8 H9 N S)'
_chemical_formula_sum            'C22 H18 F4 I2 N2 S2'
_chemical_formula_weight         704.32
_chemical_name_common
;                 
2-methylthiobenzamide & 
1,4-diiodotetrafluorobenzene (2:1) cocrystal 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                97.9080(10)
_cell_angle_beta                 93.2950(10)
_cell_angle_gamma                112.0730(10)
_cell_formula_units_Z            1
_cell_length_a                   8.1916(4)
_cell_length_b                   8.6229(4)
_cell_length_c                   9.6939(5)
_cell_measurement_reflns_used    7524
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      26.4330
_cell_measurement_theta_min      2.7024
_cell_volume                     624.05(5)
_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      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & 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  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13984
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    2.730
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.990
_refine_diff_density_min         -1.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0347
_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)+(0.0537P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                2302
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00513_si_002.cif
_cod_data_source_block           3_2.1
_cod_depositor_comments
'Adding full bibliography for 4513250--4513263.cif.'
_cod_original_formula_sum        'C22 H18 F4 I2 N2 S2 '
_cod_database_code               4513252
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C C1 0.7131(5) 0.7157(4) 0.1465(4) 0.0510(7) Uani d . 1
C C2 0.6422(6) 0.6099(4) 0.2415(4) 0.0615(9) Uani d . 1
C C3 0.7395(8) 0.5118(5) 0.2844(5) 0.0830(15) Uani d . 1
H H3 0.6976 0.4404 0.3493 0.1 Uiso calc R 1
C C4 0.8915(8) 0.5238(7) 0.2303(8) 0.0990(19) Uani d . 1
H H4 0.9508 0.458 0.258 0.119 Uiso calc R 1
C C5 0.9607(7) 0.6274(7) 0.1376(7) 0.0946(17) Uani d . 1
H H5 1.0654 0.6327 0.1021 0.114 Uiso calc R 1
C C6 0.8730(6) 0.7247(6) 0.0967(6) 0.0746(12) Uani d . 1
H H6 0.921 0.7983 0.0346 0.09 Uiso calc R 1
C C7 0.6281(4) 0.8280(4) 0.0993(3) 0.0434(6) Uani d . 1
S S8 0.72696(12) 1.03778(10) 0.14837(10) 0.0556(2) Uani d . 1
H H9A 0.456(7) 0.653(7) -0.011(6) 0.078(14) Uiso d . 1
H H9B 0.418(5) 0.811(5) -0.005(4) 0.061(11) Uiso d D 1
N N9 0.4743(4) 0.7533(4) 0.0190(4) 0.0581(7) Uani d D 1
C C10 0.4825(8) 0.5992(7) 0.2996(6) 0.0913(15) Uani d . 1
H H10A 0.4705 0.7062 0.3046 0.137 Uiso calc R 1
H H10B 0.4873 0.5719 0.3921 0.137 Uiso calc R 1
H H10C 0.3827 0.5122 0.2411 0.137 Uiso calc R 1
C C11 0.1468(4) 0.0203(4) 0.4254(3) 0.0451(6) Uani d . 1
C C12 0.0662(4) 0.1354(4) 0.4312(3) 0.0472(7) Uani d . 1
C C13 -0.0781(4) 0.1155(4) 0.5038(3) 0.0457(7) Uani d . 1
I I14 0.36439(3) 0.04612(3) 0.31551(2) 0.06241(13) Uani d . 1
F F15 0.1283(3) 0.2689(3) 0.3657(2) 0.0653(5) Uani d . 1
F F16 -0.1512(3) 0.2312(3) 0.5042(2) 0.0618(5) 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'
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
C2 C1 C6 . . 119.9(3)
C2 C1 C7 . . 121.8(3)
C6 C1 C7 . . 118.2(3)
C1 C2 C10 . . 122.6(4)
C1 C2 C3 . . 117.1(4)
C10 C2 C3 . . 120.3(4)
C4 C3 C2 . . 120.0(5)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C5 C4 C3 . . 122.8(5)
C5 C4 H4 . . 118.6
C3 C4 H4 . . 118.6
C4 C5 C6 . . 118.6(5)
C4 C5 H5 . . 120.7
C6 C5 H5 . . 120.7
C5 C6 C1 . . 121.5(5)
C5 C6 H6 . . 119.2
C1 C6 H6 . . 119.2
N9 C7 C1 . . 117.1(3)
N9 C7 S8 . . 123.0(2)
C1 C7 S8 . . 120.0(2)
C7 N9 H9A . . 111.(4)
C7 N9 H9B . . 120.(3)
H9A N9 H9B . . 128.(5)
C2 C10 H10A . . 109.5
C2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C12 C11 C13 . 2_556 117.6(3)
C12 C11 I14 . . 122.1(2)
C13 C11 I14 2_556 . 120.3(2)
F15 C12 C13 . . 119.0(3)
F15 C12 C11 . . 119.9(3)
C13 C12 C11 . . 121.2(3)
F16 C13 C12 . . 118.2(3)
F16 C13 C11 . 2_556 120.6(3)
C12 C13 C11 . 2_556 121.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.383(5)
C1 C6 . 1.400(6)
C1 C7 . 1.492(4)
C2 C10 . 1.430(7)
C2 C3 . 1.445(6)
C3 C4 . 1.353(9)
C3 H3 . 0.93
C4 C5 . 1.351(9)
C4 H4 . 0.93
C5 C6 . 1.375(7)
C5 H5 . 0.93
C6 H6 . 0.93
C7 N9 . 1.322(4)
C7 S8 . 1.665(3)
N9 H9A . 0.83(6)
N9 H9B . 0.843(19)
C10 H10A . 0.96
C10 H10B . 0.96
C10 H10C . 0.96
C11 C12 . 1.381(4)
C11 C13 2_556 1.389(4)
C11 I14 . 2.085(3)
C12 F15 . 1.336(4)
C12 C13 . 1.377(5)
C13 F16 . 1.342(4)
C13 C11 2_556 1.389(4)
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 H9B S8 2_675 0.843(19) 2.55(2) 3.365(3) 163.(4)
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_4
_geom_torsion
C6 C1 C2 C10 . . 177.9(4)
C7 C1 C2 C10 . . 0.7(6)
C6 C1 C2 C3 . . -0.3(5)
C7 C1 C2 C3 . . -177.5(3)
C1 C2 C3 C4 . . -1.0(6)
C10 C2 C3 C4 . . -179.3(4)
C2 C3 C4 C5 . . 1.2(7)
C3 C4 C5 C6 . . 0.1(8)
C4 C5 C6 C1 . . -1.4(7)
C2 C1 C6 C5 . . 1.5(6)
C7 C1 C6 C5 . . 178.8(4)
C2 C1 C7 N9 . . -69.1(4)
C6 C1 C7 N9 . . 113.7(4)
C2 C1 C7 S8 . . 110.7(3)
C6 C1 C7 S8 . . -66.5(4)
C13 C11 C12 F15 2_556 . 179.5(3)
I14 C11 C12 F15 . . -0.4(4)
C13 C11 C12 C13 2_556 . -0.5(5)
I14 C11 C12 C13 . . 179.6(2)
F15 C12 C13 F16 . . 0.6(4)
C11 C12 C13 F16 . . -179.4(3)
F15 C12 C13 C11 . 2_556 -179.5(3)
C11 C12 C13 C11 . 2_556 0.5(5)
