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_7215745
_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         'C4 H8 O2 S2'
_chemical_formula_sum            'C4 H8 O2 S2'
_chemical_formula_weight         152.22
_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
_audit_creation_date             2012-03-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.161(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2950(3)
_cell_length_b                   6.3948(5)
_cell_length_c                   8.090(3)
_cell_measurement_reflns_used    1133
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      31.7911
_cell_measurement_theta_min      3.1772
_cell_volume                     315.77(12)
_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 0.975
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details
;
  1 omega  -68.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672   19.0000   30.0000 111

  2 omega  -89.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000   60.0000 40

  3 omega   21.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   77.0000 -150.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0308685000
_diffrn_orient_matrix_UB_12      0.0511821000
_diffrn_orient_matrix_UB_13      0.0803187000
_diffrn_orient_matrix_UB_21      -0.0958459000
_diffrn_orient_matrix_UB_22      -0.0380141000
_diffrn_orient_matrix_UB_23      0.0208634000
_diffrn_orient_matrix_UB_31      0.0573845000
_diffrn_orient_matrix_UB_32      -0.0906189000
_diffrn_orient_matrix_UB_33      0.0364965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1632
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_min         3.69
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   analytical
_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)
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_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.2065
_exptl_crystal_size_min          0.1504
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     37
_refine_ls_number_reflns         973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0292
_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/[\s^2^(Fo^2^)+(0.0386P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                866
_reflns_number_total             973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1217
_cod_original_cell_volume        315.78(11)
_cod_database_code               7215745
_chemical_oxdiff_formula         'C4 H8 O2 S2'
_chemical_oxdiff_usercomment     'Akihiro AT33 - A'
_reflns_odcompleteness_completeness 97.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01