Finding the Perfect Match: Halogen vs Hydrogen Bonding
Shirman, Tanya; Boterashvili, Meital; Orbach, Meital; Freeman, Dalia; Shimon, Linda J. W.; Lahav, Michal; van der Boom, Milko E.; Crystal Growth & Design 15 (2015) 4756–; doi:10.1021/acs.cgd.5b01260

data_4516520
_publ_section_title
;
 Finding the Perfect Match: Halogen vs Hydrogen Bonding
;
_journal_issue                   10
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4756
_journal_paper_doi               10.1021/acs.cgd.5b01260
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C13 H6 Br F4 N O, 0.5(H2 O)'
_chemical_formula_sum            'C13 H7 Br F4 N O1.5'
_chemical_formula_weight         357.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.609(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.4609(10)
_cell_length_b                   7.0954(3)
_cell_length_c                   15.6162(8)
_cell_measurement_reflns_used    33058
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.36
_cell_measurement_theta_min      1.81
_cell_volume                     2499.9(2)
_computing_cell_refinement       'Bruker Apex2'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker KappaApexII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33058
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.362
_diffrn_reflns_theta_min         1.805
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    3.337
_exptl_absorpt_correction_T_max  0.6523
_exptl_absorpt_correction_T_min  0.5272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       prism
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.446
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+2.1708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4213
_reflns_number_total             4773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5b01260_si_004.cif
_cod_data_source_block           v137n
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C13 H7 Br F4 N O1.50'
_cod_database_code               4516520
_shelx_estimated_absorpt_t_min   0.527
_shelx_estimated_absorpt_t_max   0.652
_shelxl_version_number           2013-4
_shelx_res_checksum              23670
_shelx_hkl_checksum              1668