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_7215744
_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(C7 F4 I O2), 2(C4 H10 N S), C4 H9 N S'
_chemical_formula_sum            'C26 H29 F8 I2 N3 O4 S3'
_chemical_formula_weight         949.50
_chemical_name_systematic
;
 ? 
;
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-18
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                107.044(11)
_cell_angle_beta                 99.741(10)
_cell_angle_gamma                92.149(10)
_cell_formula_units_Z            1
_cell_length_a                   5.7209(7)
_cell_length_b                   10.3273(13)
_cell_length_c                   14.4539(17)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      29.7735
_cell_measurement_theta_min      2.9997
_cell_volume                     801.24(18)
_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 0.99
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details
;
  1 omega  -91.00   -2.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -77.0000   90.0000 89

  2 omega    6.00   46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517   77.0000 -150.0000 40

  3 omega  -50.00   46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517   77.0000  -60.0000 96

  4 omega  -43.00   -9.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -78.0000   16.0000 34

  5 omega  -89.00   10.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -77.0000 -180.0000 99

  6 omega    1.00   35.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5455  -57.0000  -30.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1016886000
_diffrn_orient_matrix_UB_12      0.0463827000
_diffrn_orient_matrix_UB_13      0.0089145000
_diffrn_orient_matrix_UB_21      -0.0349165000
_diffrn_orient_matrix_UB_22      0.0407230000
_diffrn_orient_matrix_UB_23      0.0433870000
_diffrn_orient_matrix_UB_31      0.0664295000
_diffrn_orient_matrix_UB_32      -0.0371042000
_diffrn_orient_matrix_UB_33      0.0278676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6397
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.86
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.876
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.1982
_exptl_crystal_size_mid          0.0576
_exptl_crystal_size_min          0.0177
_refine_diff_density_max         3.307
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0383P)^2^+2.2099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3224
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1234
_cod_original_cell_volume        801.23(17)
_cod_database_code               7215744
_chemical_oxdiff_formula         'C11 H10 F4 I1 N1 O2 S1'
_chemical_oxdiff_usercomment     'Akihiro AT48 C2A'
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50