Structural Competition between Hydrogen Bonds and Halogen Bonds
Christer B. Aakeröy; Meg Fasulo; Nate Schultheiss; John Desper; Curtis Moore; Journal of the American Chemical Society 129 (2007) 13772–13773; doi:10.1021/ja073201c

data_4110142
_publ_section_title
;
 Structural Competition between Hydrogen Bonds and Halogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13772
_journal_page_last               13773
_journal_paper_doi               10.1021/ja073201c
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety
;
(C13 H11 N3) (C7 H2 F4 N O Br)
;
_chemical_formula_sum            'C20 H13 Br F4 N4 O'
_chemical_formula_weight         481.25
_chemical_name_systematic
;
MF-24-58 1-methyl-2-(4-pyridyl)benzimidazole, 4-Br-F4-PhCH=NOH
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8554(3)
_cell_length_b                   7.9485(4)
_cell_length_c                   34.9508(15)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.2
_cell_measurement_theta_min      3.10
_cell_volume                     1904.47(15)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            65778
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       Needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0350P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.714
_reflns_number_gt                3469
_reflns_number_total             4205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja073201csi20070506_021240_4.cif
_cod_data_source_block           13
_cod_database_code               4110142