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_7215748
_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         'C6 H F4 I O, C10 H8 N2'
_chemical_formula_sum            'C16 H9 F4 I N2 O'
_chemical_formula_weight         448.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.546(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0299(11)
_cell_length_b                   4.0059(2)
_cell_length_c                   25.154(3)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      27.9910
_cell_measurement_theta_min      3.5260
_cell_volume                     1548.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9928
_diffrn_measurement_details
;
  1 omega  -13.00   25.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1611  -99.0000 -180.0000 38

  2 omega   59.00   88.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111  178.0000  150.0000 29

  3 omega  -14.00   57.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111  -99.0000  -30.0000 71

  4 omega  -27.00   43.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111   19.0000 -150.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0298450000
_diffrn_orient_matrix_UB_12      0.0747222000
_diffrn_orient_matrix_UB_13      0.0125491000
_diffrn_orient_matrix_UB_21      -0.0087977000
_diffrn_orient_matrix_UB_22      0.1269109000
_diffrn_orient_matrix_UB_23      -0.0204771000
_diffrn_orient_matrix_UB_31      -0.0340654000
_diffrn_orient_matrix_UB_32      -0.0982161000
_diffrn_orient_matrix_UB_33      -0.0170048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4832
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.118
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2442
_exptl_crystal_size_mid          0.0622
_exptl_crystal_size_min          0.0253
_refine_diff_density_max         1.648
_refine_diff_density_min         -1.952
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0651
_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^)+(0.0139P)^2^+15.1259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2443
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1215
_cod_database_code               7215748
_chemical_oxdiff_formula         'C16 H9 F4 I1 N2 O1'
_chemical_oxdiff_usercomment     'Akihiro Takemura AT27-B3'
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C4) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16)
;