#------------------------------------------------------------------------------
#$Date: 2015-07-05 10:48:00 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140072 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/32/4513260.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_4513260
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, C7 H6 F N S '
_chemical_formula_sum            'C13 H6 F5 I2 N S'
_chemical_formula_weight         557.05
_chemical_name_common
;                 
2-fluorothiobenzamide & 
1,4-diiodotetrafluorobenzene (1:1) 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                110.5560(10)
_cell_angle_beta                 96.2050(10)
_cell_angle_gamma                102.9010(10)
_cell_formula_units_Z            2
_cell_length_a                   6.2828(3)
_cell_length_b                   10.9161(5)
_cell_length_c                   12.9878(6)
_cell_measurement_reflns_used    3202
_cell_measurement_temperature    294.(2)
_cell_measurement_theta_max      25.3907
_cell_measurement_theta_min      3.2437
_cell_volume                     795.83(6)
_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      294.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.1186
_diffrn_reflns_av_sigmaI/netI    0.0782
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8688
_diffrn_reflns_theta_full        25.82
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    4.127
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.707
_refine_ls_extinction_coef       0.0230(9)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0380
_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)+(0.0232P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                2402
_reflns_number_total             3025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00513_si_002.cif
_cod_data_source_block           12.1
_cod_depositor_comments
'Adding full bibliography for 4513250--4513263.cif.'
_cod_database_code               4513260
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 0.2204(8) 0.8734(5) 0.2376(4) 0.0422(11) Uani d . 1
C C2 0.1500(11) 0.8992(6) 0.3385(5) 0.0590(15) Uani d . 1
C C3 0.2295(12) 0.8583(7) 0.4198(5) 0.0757(19) Uani d . 1
H H3 0.179 0.8793 0.4869 0.091 Uiso calc R 1
C C4 0.3844(11) 0.7859(6) 0.4012(5) 0.0712(18) Uani d . 1
H H4 0.4414 0.7585 0.4559 0.085 Uiso calc R 1
C C5 0.4536(11) 0.7549(6) 0.3011(5) 0.0646(15) Uani d . 1
H H5 0.554 0.7029 0.2868 0.077 Uiso calc R 1
C C6 0.3772(9) 0.7991(5) 0.2215(4) 0.0517(13) Uani d . 1
H H6 0.431 0.7793 0.1553 0.062 Uiso calc R 1
C C7 0.1449(8) 0.9226(5) 0.1503(4) 0.0447(12) Uani d . 1
S S8 0.3046(2) 0.94591(15) 0.06019(11) 0.0546(4) Uani d . 1
H H9A -0.093(10) 0.982(6) 0.104(4) 0.07(2) Uiso d D 1
H H9B -0.149(9) 0.923(6) 0.179(5) 0.08(2) Uiso d D 1
N N9 -0.0525(9) 0.9450(6) 0.1446(5) 0.0627(13) Uani d D 1
F F10 -0.0058(7) 0.9701(4) 0.3595(3) 0.0883(13) Uani d . 1
C C11 0.1094(8) 0.4345(5) 0.0552(4) 0.0403(11) Uani d . 1
C C12 0.1506(8) 0.4382(5) -0.0460(4) 0.0460(12) Uani d . 1
C C13 -0.0447(9) 0.4997(5) 0.1001(4) 0.0465(12) Uani d . 1
I I14 0.27715(7) 0.34350(4) 0.14011(4) 0.06629(17) Uani d . 1
F F15 0.3013(5) 0.3769(3) -0.0923(3) 0.0693(9) Uani d . 1
F F16 -0.0912(6) 0.5038(4) 0.2005(3) 0.0689(9) Uani d . 1
C C17 0.8639(7) 0.3825(4) 0.4096(4) 0.0394(10) Uani d . 1
C C18 1.0682(8) 0.3856(5) 0.4614(4) 0.0427(11) Uani d . 1
C C19 1.2027(8) 0.4997(5) 0.5500(4) 0.0443(12) Uani d . 1
I I20 0.65726(5) 0.20784(3) 0.27776(3) 0.04557(15) Uani d . 1
F F21 1.1424(5) 0.2736(3) 0.4247(3) 0.0645(9) Uani d . 1
F F22 1.4001(5) 0.4941(3) 0.5961(3) 0.0643(9) 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 . . 115.6(5)
C2 C1 C7 . . 124.3(5)
C6 C1 C7 . . 120.1(4)
C3 C2 F10 . . 117.8(5)
C3 C2 C1 . . 123.3(5)
F10 C2 C1 . . 118.8(5)
C2 C3 C4 . . 119.4(5)
C2 C3 H3 . . 120.3
C4 C3 H3 . . 120.3
C5 C4 C3 . . 119.0(6)
C5 C4 H4 . . 120.5
C3 C4 H4 . . 120.5
C4 C5 C6 . . 121.1(6)
C4 C5 H5 . . 119.5
C6 C5 H5 . . 119.5
C5 C6 C1 . . 121.5(5)
C5 C6 H6 . . 119.2
C1 C6 H6 . . 119.2
N9 C7 C1 . . 118.4(5)
N9 C7 S8 . . 120.7(5)
C1 C7 S8 . . 120.9(4)
C7 N9 H9A . . 121.(4)
C7 N9 H9B . . 125.(5)
H9A N9 H9B . . 113.(7)
C12 C11 C13 . . 116.5(4)
C12 C11 I14 . . 122.2(4)
C13 C11 I14 . . 121.3(4)
F15 C12 C13 . 2_565 119.3(5)
F15 C12 C11 . . 118.5(5)
C13 C12 C11 2_565 . 122.2(5)
C12 C13 F16 2_565 . 118.3(5)
C12 C13 C11 2_565 . 121.3(5)
F16 C13 C11 . . 120.3(5)
C18 C17 C19 . 2_766 116.9(4)
C18 C17 I20 . . 122.1(3)
C19 C17 I20 2_766 . 121.0(3)
F21 C18 C17 . . 119.3(4)
F21 C18 C19 . . 118.4(4)
C17 C18 C19 . . 122.2(4)
F22 C19 C18 . . 118.4(4)
F22 C19 C17 . 2_766 120.7(4)
C18 C19 C17 . 2_766 120.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.384(7)
C1 C6 . 1.398(7)
C1 C7 . 1.491(7)
C2 C3 . 1.371(8)
C2 F10 . 1.370(6)
C3 C4 . 1.375(9)
C3 H3 . 0.93
C4 C5 . 1.369(8)
C4 H4 . 0.93
C5 C6 . 1.371(8)
C5 H5 . 0.93
C6 H6 . 0.93
C7 N9 . 1.316(7)
C7 S8 . 1.671(5)
N9 H9A . 0.82(2)
N9 H9B . 0.84(2)
C11 C12 . 1.380(7)
C11 C13 . 1.387(7)
C11 I14 . 2.073(5)
C12 F15 . 1.353(5)
C12 C13 2_565 1.353(7)
C13 C12 2_565 1.353(7)
C13 F16 . 1.355(6)
C17 C18 . 1.370(7)
C17 C19 2_766 1.384(6)
C17 I20 . 2.092(4)
C18 F21 . 1.354(5)
C18 C19 . 1.380(7)
C19 F22 . 1.341(5)
C19 C17 2_766 1.384(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 H9B F10 . 0.84(2) 2.24(6) 2.683(7) 113.(5)
N9 H9A S8 2_575 0.82(2) 2.82(2) 3.628(6) 168.(6)
