Structural Investigation of Weak Intermolecular Interactions (Hydrogen and Halogen Bonds) in Fluorine-Substituted Benzimidazoles
Pérez-Torralba, Marta; García, M. Ángeles; López, Concepción; Torralba, M. Carmen; Torres, M. Rosario; Claramunt, Rosa M.; Elguero, José; Crystal Growth & Design 14 (2014) 3499–; doi:10.1021/cg500442k

data_4511248
_publ_section_title
;
 Structural Investigation of Weak Intermolecular Interactions (Hydrogen
 and Halogen Bonds) in Fluorine-Substituted Benzimidazoles
;
_journal_issue                   7
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3499
_journal_paper_doi               10.1021/cg500442k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C8 H4 F4 N2 O'
_chemical_formula_weight         220.13
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.503(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2581(11)
_cell_length_b                   5.4872(5)
_cell_length_c                   13.5463(13)
_cell_measurement_reflns_used    1923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.63
_cell_volume                     820.02(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7291
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                1123
_reflns_number_total             1962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500442k_si_001.cif
_cod_data_source_block           C8H4F4N2O_(4_polymorph_I)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4511245--4511251.cif.
;
_cod_original_cell_volume        820.02(13)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4511248