#------------------------------------------------------------------------------
#$Date: 2015-07-05 10:48:00 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140072 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/32/4513259.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_4513259
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 N2 O2 S)'
_chemical_formula_sum            'C20 H12 F4 I2 N4 O4 S2'
_chemical_formula_weight         766.28
_chemical_name_common
;                 
3-nitrothiobenzamide & 
1,4-diiodotetrafluorobenzene (4:3) cocrystal 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.258(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1924(7)
_cell_length_b                   14.745(2)
_cell_length_c                   16.356(3)
_cell_measurement_reflns_used    4926
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      23.2624
_cell_measurement_theta_min      2.5131
_cell_volume                     1239.3(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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18967
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    2.772
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0246
_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)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                1793
_reflns_number_total             2220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00513_si_002.cif
_cod_data_source_block           10_2.1
_cod_depositor_comments
'Adding full bibliography for 4513250--4513263.cif.'
_cod_database_code               4513259
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.9424(7) 0.4176(3) 0.3431(2) 0.0315(9) Uani d . 1
C C2 0.9104(8) 0.3320(3) 0.3086(3) 0.0351(10) Uani d . 1
H H2 0.792 0.2913 0.3256 0.042 Uiso calc R 1
C C3 1.0595(9) 0.3083(3) 0.2478(3) 0.0400(10) Uani d . 1
C C4 1.2375(9) 0.3651(3) 0.2210(3) 0.0455(11) Uani d . 1
H H4 1.3354 0.3469 0.1805 0.055 Uiso calc R 1
C C5 1.2676(8) 0.4508(3) 0.2559(3) 0.0462(11) Uani d . 1
H H5 1.3868 0.4911 0.2387 0.055 Uiso calc R 1
C C6 1.1216(7) 0.4768(3) 0.3162(3) 0.0391(10) Uani d . 1
H H6 1.1432 0.5345 0.3391 0.047 Uiso calc R 1
C C7 0.7857(8) 0.4444(3) 0.4086(3) 0.0343(9) Uani d . 1
S S8 0.6822(3) 0.36813(8) 0.47229(8) 0.0494(3) Uani d . 1
H H9B 0.774(8) 0.567(3) 0.378(2) 0.047(14) Uiso d D 1
N N9 0.7313(8) 0.5310(3) 0.4131(3) 0.0448(9) Uani d D 1
N N10 1.0205(10) 0.2167(3) 0.2113(3) 0.0604(12) Uani d . 1
O O11 0.8457(11) 0.1703(3) 0.2291(3) 0.0997(17) Uani d . 1
O O12 1.1658(10) 0.1923(3) 0.1636(3) 0.0900(15) Uani d . 1
C C13 0.6615(8) 0.9232(3) 0.5007(3) 0.0390(10) Uani d . 1
C C14 0.6453(7) 0.9864(3) 0.4381(3) 0.0407(10) Uani d . 1
C C15 0.4857(8) 1.0613(3) 0.4366(3) 0.0415(10) Uani d . 1
I I16 0.89991(6) 0.80832(2) 0.50240(2) 0.04852(15) Uani d . 1
F F17 0.7875(5) 0.9758(2) 0.37560(17) 0.0580(7) Uani d . 1
F F18 0.4780(5) 1.11998(19) 0.37318(16) 0.0588(7) Uani d . 1
H H9A 0.643(7) 0.549(3) 0.4507(19) 0.033(12) Uiso d 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'
O O 0.0106 0.0060 '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 . . 119.3(4)
C2 C1 C7 . . 119.3(4)
C6 C1 C7 . . 121.4(4)
C1 C2 C3 . . 118.3(4)
C1 C2 H2 . . 120.8
C3 C2 H2 . . 120.8
C4 C3 C2 . . 123.3(4)
C4 C3 N10 . . 119.4(4)
C2 C3 N10 . . 117.4(4)
C3 C4 C5 . . 117.9(4)
C3 C4 H4 . . 121.1
C5 C4 H4 . . 121.1
C6 C5 C4 . . 120.4(4)
C6 C5 H5 . . 119.8
C4 C5 H5 . . 119.8
C5 C6 C1 . . 120.8(4)
C5 C6 H6 . . 119.6
C1 C6 H6 . . 119.6
N9 C7 C1 . . 116.3(4)
N9 C7 S8 . . 121.8(3)
C1 C7 S8 . . 121.8(3)
C7 N9 H9B . . 120.(3)
C7 N9 H9A . . 119.(3)
H9B N9 H9A . . 121.(4)
O11 N10 O12 . . 123.1(5)
O11 N10 C3 . . 119.0(4)
O12 N10 C3 . . 117.9(5)
C14 C13 C15 . 3_676 117.3(4)
C14 C13 I16 . . 122.0(3)
C15 C13 I16 3_676 . 120.8(3)
F17 C14 C15 . . 118.0(4)
F17 C14 C13 . . 120.1(4)
C15 C14 C13 . . 121.8(4)
F18 C15 C14 . . 118.7(4)
F18 C15 C13 . 3_676 120.4(4)
C14 C15 C13 . 3_676 120.9(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(5)
C1 C6 . 1.392(6)
C1 C7 . 1.488(5)
C2 C3 . 1.389(6)
C2 H2 . 0.93
C3 C4 . 1.365(7)
C3 N10 . 1.479(5)
C4 C5 . 1.387(6)
C4 H4 . 0.93
C5 C6 . 1.381(6)
C5 H5 . 0.93
C6 H6 . 0.93
C7 N9 . 1.313(5)
C7 S8 . 1.673(4)
N9 H9B . 0.833(19)
N9 H9A . 0.859(19)
N10 O11 . 1.205(6)
N10 O12 . 1.215(6)
C13 C14 . 1.378(6)
C13 C15 3_676 1.384(6)
C13 I16 . 2.096(4)
C14 F17 . 1.353(5)
C14 C15 . 1.379(6)
C15 F18 . 1.346(5)
C15 C13 3_676 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 H9A S8 3_666 0.859(19) 2.56(2) 3.389(4) 163.(4)
N9 H9B O11 2_655 0.833(19) 2.34(3) 3.086(6) 150.(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 C3 . . -0.1(6)
C7 C1 C2 C3 . . -179.8(4)
C1 C2 C3 C4 . . 0.6(7)
C1 C2 C3 N10 . . -179.6(4)
C2 C3 C4 C5 . . -0.7(7)
N10 C3 C4 C5 . . 179.5(4)
C3 C4 C5 C6 . . 0.3(7)
C4 C5 C6 C1 . . 0.2(7)
C2 C1 C6 C5 . . -0.3(6)
C7 C1 C6 C5 . . 179.4(4)
C2 C1 C7 N9 . . -150.5(4)
C6 C1 C7 N9 . . 29.9(6)
C2 C1 C7 S8 . . 29.0(5)
C6 C1 C7 S8 . . -150.7(3)
C4 C3 N10 O11 . . -172.7(5)
C2 C3 N10 O11 . . 7.5(7)
C4 C3 N10 O12 . . 6.4(7)
C2 C3 N10 O12 . . -173.5(5)
C15 C13 C14 F17 3_676 . 179.0(4)
I16 C13 C14 F17 . . -0.6(6)
C15 C13 C14 C15 3_676 . -1.3(7)
I16 C13 C14 C15 . . 179.1(3)
F17 C14 C15 F18 . . 0.2(6)
C13 C14 C15 F18 . . -179.5(4)
F17 C14 C15 C13 . 3_676 -178.9(4)
C13 C14 C15 C13 . 3_676 1.3(7)
