Hydrogen bonding vs. halogen bonding: the solvent decides
Robertson, Craig. C.; Wright, James S.; Carrington, Elliot J.; Perutz, Robin N.; Hunter, Christopher A.; Brammer, Lee; Chem. Sci.  (2017) –; doi:10.1039/C7SC01801K

data_1546180
_publ_section_title
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 Hydrogen bonding vs. halogen bonding: the solvent decides
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01801K
_journal_year                    2017
_chemical_formula_moiety         'C12 H12 N2, C6 H2 F4 O2'
_chemical_formula_sum            'C18 H14 F4 N2 O2'
_chemical_formula_weight         366.31
_chemical_name_systematic
'1,2-Bis(4-pyridyl)ethane tetrafluorohydroquinone co-crystal'
_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     direct
_audit_creation_date             2016-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-09 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                86.863(5)
_cell_angle_beta                 75.722(5)
_cell_angle_gamma                71.755(4)
_cell_formula_units_Z            1
_cell_length_a                   6.1939(4)
_cell_length_b                   7.4692(5)
_cell_length_c                   9.0672(6)
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.782
_cell_measurement_theta_min      2.318
_cell_volume                     385.97(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6725
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.318
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0491 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_recrystallization_method 'co-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.1800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1373
_reflns_number_total             1778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01801k2.cif
_cod_data_source_block           ilb2850_0m
_cod_database_code               1546180
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-01-12
_olex2_submission_original_sample_id ccrx17HB
_olex2_submission_special_instructions 'No special instructions were received'