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_7215742
_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_absolute_configuration unk
_chemical_formula_moiety         'C7 H F4 I O2'
_chemical_formula_sum            'C7 H F4 I O2'
_chemical_formula_weight         319.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2012-05-29
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.548(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7596(2)
_cell_length_b                   31.6474(8)
_cell_length_c                   7.9922(3)
_cell_measurement_reflns_used    10149
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0135
_cell_measurement_theta_min      2.9747
_cell_volume                     1620.91(9)
_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
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.922536
_diffrn_measurement_details
;
  1 omega  -90.00   -3.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000   51.0000 174

  2 omega  -56.00  -14.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -134.0000 84

  3 omega  -64.00  -39.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -128.0000 50

  4 omega  -88.00  -61.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -134.0000 54

  5 omega   16.00   41.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759 -109.0000  128.0000 50

  6 omega   16.00   41.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759 -109.0000  134.0000 50

  7 omega  -23.00    4.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.6250  109.0000 -128.0000 54

  8 omega  -64.00   46.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259   37.0000  -90.0000 220

  9 omega -105.00   -4.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  -57.0000  120.0000 202

 10 omega   -6.00   32.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759  -57.0000    0.0000 76

 11 omega  -18.00    7.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.4821  -77.0000 -180.0000 50

 12 omega -103.00  -77.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.4821  -77.0000 -180.0000 52
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0174970000
_diffrn_orient_matrix_UB_12      0.0217969000
_diffrn_orient_matrix_UB_13      -0.0101379000
_diffrn_orient_matrix_UB_21      0.0959032000
_diffrn_orient_matrix_UB_22      -0.0012202000
_diffrn_orient_matrix_UB_23      0.0698912000
_diffrn_orient_matrix_UB_31      0.0522487000
_diffrn_orient_matrix_UB_32      -0.0050475000
_diffrn_orient_matrix_UB_33      -0.0616208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15874
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.989
_exptl_absorpt_correction_T_max  0.434
_exptl_absorpt_correction_T_min  0.140
_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    2.6222
_exptl_crystal_F_000             1181.6836
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.1624
_exptl_crystal_size_min          0.0939
_refine_diff_density_max         0.977794
_refine_diff_density_min         -1.499360
_refine_diff_density_rms         0.162151
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.43(2)
_refine_ls_d_res_high            0.709010
_refine_ls_d_res_low             6.833966
_refine_ls_goodness_of_fit_ref   1.046121
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8789
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.037133
_refine_ls_R_factor_all          0.035918
_refine_ls_R_factor_gt           0.034122
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+6.5845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.084841
_reflns_Friedel_coverage         0.851
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              44
_reflns_limit_k_min              -44
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                8382
_reflns_number_total             8789
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1239a
_cod_original_cell_volume        1620.92(9)
_cod_database_code               7215742
_chemical_oxdiff_formula         'C7 H1 F4 I1 O2'
_chemical_oxdiff_usercomment     'Akihiro AT44 L'
_reflns_odcompleteness_completeness 99.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01