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_1546179
_publ_section_title
;
 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         'C6 H5 F1 O2, C12 H12 N2'
_chemical_formula_sum            'C18 H17 F N2 O2'
_chemical_formula_weight         312.33
_chemical_name_systematic
'1,2(bis-4-pyridyl)ethane fluorohydroquinone 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                95.669(10)
_cell_angle_beta                 91.769(11)
_cell_angle_gamma                107.117(13)
_cell_formula_units_Z            2
_cell_length_a                   7.1689(13)
_cell_length_b                   9.2830(15)
_cell_length_c                   11.8655(16)
_cell_measurement_reflns_used    2033
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.954
_cell_measurement_theta_min      3.751
_cell_volume                     749.5(2)
_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      100.0
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7125
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        66.961
_diffrn_reflns_theta_max         66.961
_diffrn_reflns_theta_min         3.751
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.7600.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method 'co-crystallisation from solvent'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0701
_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^)+(0.1333P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             2511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01801k2.cif
_cod_data_source_block           ilb2814_0m
_cod_database_code               1546179
_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. Others
 Sof(F1B)=Sof(H14)=1-FVAR(1)
 Sof(F1A)=Sof(H18)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C18(H18), C1(H1), C2(H2), C4(H4), C5(H5), C9(H9),
 C10(H10), C11(H11), C12(H12), C15(H15)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2014-12-09
_olex2_date_sample_submission    2014-12-09
_olex2_submission_original_sample_id
'1,2(bis-4-pyridyl)ethane fluorohydroquinone cocrx'
_olex2_submission_special_instructions 'No special instructions were received'