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_7215746
_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 Br F4 O), C4 H8 O2 S2 '
_chemical_formula_sum            'C16 H10 Br2 F8 O4 S2'
_chemical_formula_weight         642.18
_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             2013-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.557(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.89886(16)
_cell_length_b                   21.0112(5)
_cell_length_c                   16.1143(4)
_cell_measurement_reflns_used    4317
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.8210
_cell_measurement_theta_min      3.1540
_cell_volume                     1987.85(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0465490000
_diffrn_orient_matrix_UB_12      -0.0292104000
_diffrn_orient_matrix_UB_13      -0.0124119000
_diffrn_orient_matrix_UB_21      -0.0025336000
_diffrn_orient_matrix_UB_22      0.0114268000
_diffrn_orient_matrix_UB_23      -0.0415179000
_diffrn_orient_matrix_UB_31      0.1114328000
_diffrn_orient_matrix_UB_32      0.0124767000
_diffrn_orient_matrix_UB_33      0.0088822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11592
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.386
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.3096
_exptl_crystal_size_mid          0.0734
_exptl_crystal_size_min          0.0333
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0297P)^2^+0.6326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                3503
_reflns_number_total             4103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00319e1.cif
_cod_data_source_block           dwb1373
_cod_database_code               7215746
_chemical_oxdiff_formula         'C16 H10 Br2 F8 O4 S2'
_chemical_oxdiff_usercomment     'Linda E348D'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
;