Structure determination of three furan-substituted benzimidazoles and calculation of π–π and C—H···π interaction energies
Geiger, David K.; Geiger, H. Cristina; Deck, Jared M.; Acta Crystallographica Section C 70 (2014) –; doi:10.1107/S205322961402405X

data_2019719
_publ_section_title
;
 Structure determination of three furan-substituted benzimidazoles and
 calculation of \p--\p and C---H&#x00B7;&#x00B7;&#x00B7;\p interaction
 energies
;
_journal_coeditor_code           LG3149
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961402405X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H13 N2 O2 +, Cl -, H2 O'
_chemical_formula_moiety         'C16 H13 N2 O2 +, Cl -, H2 O'
_chemical_formula_sum            'C16 H15 Cl N2 O3'
_chemical_formula_weight         318.75
_chemical_name_systematic
;
2-(Furan-2-yl)-1-[(furan-2-yl)methyl]-1<i>H</i>-benzimidazol-3-ium chloride
monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.050(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8700(7)
_cell_length_b                   18.694(3)
_cell_length_c                   17.196(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      19.0151
_cell_measurement_theta_min      5.3819
_cell_volume                     1550.1(4)
_computing_cell_refinement
;
APEX2 (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           'Mo Ka'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7314
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.207
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1034 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0276P)^2^+0.1149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2420
_reflns_number_total             2685
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lg3149sup1.cif
_cod_data_source_block           II
_cod_database_code               2019719
_cod_database_fobs_code          2019719
_shelx_hkl_checksum              14983
_shelx_res_checksum              4374