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_7215747
_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         '2(C6 H F4 I O), C4 H8 O S'
_chemical_formula_sum            'C16 H10 F8 I2 O3 S'
_chemical_formula_weight         688.10
_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             2012-04-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                75.183(14)
_cell_angle_beta                 74.084(13)
_cell_angle_gamma                79.202(14)
_cell_formula_units_Z            2
_cell_length_a                   9.1682(14)
_cell_length_b                   9.4618(16)
_cell_length_c                   12.3198(16)
_cell_measurement_reflns_used    5650
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      32.0753
_cell_measurement_theta_min      2.9270
_cell_volume                     985.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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 0.994
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details
;
  1 omega  -90.00  -45.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  178.0000  150.0000 45

  2 omega  -72.00  -46.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  110.0000  -63.0000 26

  3 omega   42.00   73.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -110.0000 -157.0000 31

  4 omega   28.00   73.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -110.0000   63.0000 45

  5 omega    7.00   93.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172   57.0000 -180.0000 86

  6 omega  -39.00   34.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000  -60.0000 73

  7 omega  -18.00   97.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172   19.0000  120.0000 115
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0457922000
_diffrn_orient_matrix_UB_12      0.0584586000
_diffrn_orient_matrix_UB_13      -0.0211799000
_diffrn_orient_matrix_UB_21      -0.0112267000
_diffrn_orient_matrix_UB_22      0.0080138000
_diffrn_orient_matrix_UB_23      -0.0561578000
_diffrn_orient_matrix_UB_31      -0.0659994000
_diffrn_orient_matrix_UB_32      0.0512240000
_diffrn_orient_matrix_UB_33      0.0127694000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10138
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.15
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.387
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method hexane
_exptl_crystal_size_max          0.1351
_exptl_crystal_size_mid          0.0888
_exptl_crystal_size_min          0.0562
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         6120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0148P)^2^+0.2966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0556
_reflns_number_gt                5357
_reflns_number_total             6120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1227
_cod_database_code               7215747
_chemical_oxdiff_formula         'C10 H9 F4 O1 I1 S1'
_chemical_oxdiff_usercomment     'Akihiro Takemura AT31A3'
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01