C—I···N and C—I···π halogen bonding in the structures of 1-benzyliodoimidazole derivatives
Nwachukwu, Chideraa I.; Bowling, Nathan P.; Bosch, Eric; Acta Crystallographica Section C 73 (2017) 2–8; doi:10.1107/S2053229616018702

data_2020684
_publ_section_title
;
 C---I&#x00B7;&#x00B7;&#x00B7;N and C---I&#x00B7;&#x00B7;&#x00B7;\p
 halogen bonding in the structures of 1-benzyliodoimidazole derivatives
;
_journal_coeditor_code           KU3188
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2
_journal_page_last               8
_journal_paper_doi               10.1107/S2053229616018702
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C10 H9 I N2'
_chemical_formula_moiety         'C10 H9 I N2'
_chemical_formula_sum            'C10 H9 I N2'
_chemical_formula_weight         284.09
_chemical_name_common
;
N-benzyl-2-iodoimidazole
;
_chemical_name_systematic
;
1-Benzyl-2-iodo-1<i>H</i>-imidazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7561(5)
_cell_length_b                   9.0016(5)
_cell_length_c                   12.8869(7)
_cell_measurement_reflns_used    7864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.76
_cell_volume                     1015.73(10)
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
XSEED (Barbour, 2001)
;
_computing_publication_material
;
XSEED (Barbour, 2001)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13262
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.087
_diffrn_reflns_theta_min         2.760
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.265
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 913 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.002(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0132
_refine_ls_R_factor_gt           0.0129
_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^)+(0.0131P)^2^+0.0966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0299
_refine_ls_wR_factor_ref         0.0300
_reflns_number_gt                2202
_reflns_number_total             2228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ku3188sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2020684--2020686.cif.'
_cod_database_code               2020684
_cod_database_fobs_code          2020684
_shelx_estimated_absorpt_t_min   0.456
_shelx_estimated_absorpt_t_max   0.860
_shelx_hkl_checksum              50519
_shelx_res_checksum              24830