Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol
Takemura, Akihiro; McAllister, Linda J.; Karadakov, Peter B.; Pridmore, Natalie E.; Whitwood, Adrian C.; Bruce, Duncan W.; CrystEngComm 16 (2014) 4254–; doi:10.1039/c4ce00319e

data_7215743
_publ_section_title
;
 Competition and cooperation: hydrogen and halogen bonding in co-crystals
 involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and
 4-bromotetrafluorophenol
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              4254
_journal_paper_doi               10.1039/c4ce00319e
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C7 H F4 I O2, 0.5(C4 H8 S2)'
_chemical_formula_sum            'C9 H5 F4 I O2 S'
_chemical_formula_weight         380.09
_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
_audit_creation_date             2012-03-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                78.743(5)
_cell_angle_beta                 75.347(5)
_cell_angle_gamma                83.455(5)
_cell_formula_units_Z            2
_cell_length_a                   6.2546(4)
_cell_length_b                   7.8761(4)
_cell_length_c                   11.5781(6)
_cell_measurement_reflns_used    8780
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0138
_cell_measurement_theta_min      2.9362
_cell_volume                     539.94(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -94.00    3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -77.0000 -180.0000 97

  2 omega  -72.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000 -120.0000 37

  3 omega  -42.00   29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000   30.0000 71

  4 omega   -2.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   82.0000    1.0000 45

  5 omega  -40.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -77.0000  -90.0000 94

  6 omega    2.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   77.0000  120.0000 95

  7 omega -101.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000   60.0000 66

  8 omega  -94.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -57.0000  -90.0000 90

  9 omega    5.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   57.0000   60.0000 90

 10 omega   35.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  178.0000  -30.0000 67

 11 omega  -20.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000   60.0000 88

 12 omega  -94.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -57.0000 -150.0000 90

 13 omega  -39.00    7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -83.0000   60.0000 46

 14 omega  -46.00   52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -37.0000  -90.0000 98

 15 omega    1.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   37.0000   30.0000 98

 16 omega  -20.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000  150.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0888221000
_diffrn_orient_matrix_UB_12      -0.0520394000
_diffrn_orient_matrix_UB_13      -0.0296917000
_diffrn_orient_matrix_UB_21      0.0282898000
_diffrn_orient_matrix_UB_22      0.0709506000
_diffrn_orient_matrix_UB_23      -0.0477690000
_diffrn_orient_matrix_UB_31      0.0711561000
_diffrn_orient_matrix_UB_32      0.0265333000
_diffrn_orient_matrix_UB_33      0.0309835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6552
_diffrn_reflns_theta_full        30.18
_diffrn_reflns_theta_max         30.18
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2195
_exptl_crystal_size_mid          0.1711
_exptl_crystal_size_min          0.1089
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         6552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0346
_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/[\s^2^(Fo^2^)+(0.0673P)^2^+0.6281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                6028
_reflns_number_total             6552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1218_twin1_hklf4
_cod_database_code               7215743
_chemical_oxdiff_formula         'C9 H5 F4 I1 O2 S'
_chemical_oxdiff_usercomment     'Akihiro AT33 - F'