#------------------------------------------------------------------------------
#$Date: 2017-02-04 05:55:54 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/06/2020684.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020684
loop_
_publ_author_name
'Nwachukwu, Chideraa I.'
'Bowling, Nathan P.'
'Bosch, Eric'
_publ_section_title
;
 C---I···N and C---I···π
 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-1H-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 x determined using 913 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  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/[σ²(Fo²)+(0.0131P)²+0.0966P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.456
_shelx_estimated_absorpt_t_max   0.860
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
I I1 0.23697(2) 0.28234(2) 0.52915(2) 0.01308(5) Uani d 1
N N1 0.1137(3) 0.4336(3) 0.72457(18) 0.0140(5) Uani d 1
C C1 0.0779(3) 0.3510(3) 0.6399(2) 0.0126(6) Uani d 1
N N2 -0.0686(3) 0.3169(3) 0.63687(19) 0.0153(5) Uani d 1
C C2 -0.1294(3) 0.3814(3) 0.7256(2) 0.0175(6) Uani d 1
H H1 -0.2337 0.3759 0.7456 0.021 Uiso calc 1
C C3 -0.0203(3) 0.4526(3) 0.7792(2) 0.0173(6) Uani d 1
H H9 -0.0329 0.5057 0.8423 0.021 Uiso calc 1
C C4 0.2632(4) 0.4913(3) 0.7544(2) 0.0163(6) Uani d 1
H H7 0.2484 0.5859 0.7923 0.020 Uiso calc 1
H H8 0.3218 0.5138 0.6906 0.020 Uiso calc 1
C C5 0.3573(3) 0.3881(3) 0.8214(2) 0.0145(6) Uani d 1
C C6 0.3217(3) 0.2395(3) 0.8364(2) 0.0165(6) Uani d 1
H H3 0.2345 0.1980 0.8035 0.020 Uiso calc 1
C C7 0.4136(3) 0.1504(4) 0.8995(2) 0.0210(7) Uani d 1
H H4 0.3885 0.0487 0.9094 0.025 Uiso calc 1
C C8 0.5407(3) 0.2094(4) 0.9477(2) 0.0215(7) Uani d 1
H H2 0.6027 0.1487 0.9909 0.026 Uiso calc 1
C C9 0.5776(4) 0.3587(4) 0.9327(2) 0.0222(7) Uani d 1
H H5 0.6647 0.4001 0.9658 0.027 Uiso calc 1
C C10 0.4869(3) 0.4463(3) 0.8693(2) 0.0177(6) Uani d 1
H H6 0.5134 0.5474 0.8583 0.021 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C3 106.4(2)
C1 N1 C4 127.8(2)
C3 N1 C4 125.8(2)
N2 C1 N1 112.1(2)
N2 C1 I1 124.0(2)
N1 C1 I1 123.9(2)
C1 N2 C2 104.5(2)
C3 C2 N2 110.5(3)
C3 C2 H1 124.7
N2 C2 H1 124.7
C2 C3 N1 106.5(3)
C2 C3 H9 126.8
N1 C3 H9 126.8
N1 C4 C5 114.8(2)
N1 C4 H7 108.6
C5 C4 H7 108.6
N1 C4 H8 108.6
C5 C4 H8 108.6
H7 C4 H8 107.5
C6 C5 C10 118.9(3)
C6 C5 C4 123.4(3)
C10 C5 C4 117.7(3)
C5 C6 C7 120.4(3)
C5 C6 H3 119.8
C7 C6 H3 119.8
C8 C7 C6 120.3(3)
C8 C7 H4 119.8
C6 C7 H4 119.8
C7 C8 C9 119.7(3)
C7 C8 H2 120.2
C9 C8 H2 120.2
C10 C9 C8 119.8(3)
C10 C9 H5 120.1
C8 C9 H5 120.1
C9 C10 C5 120.9(3)
C9 C10 H6 119.5
C5 C10 H6 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.088(3)
N1 C1 1.357(4)
N1 C3 1.379(3)
N1 C4 1.461(4)
C1 N2 1.319(3)
N2 C2 1.389(4)
C2 C3 1.341(4)
C2 H1 0.9500
C3 H9 0.9500
C4 C5 1.512(4)
C4 H7 0.9900
C4 H8 0.9900
C5 C6 1.387(4)
C5 C10 1.394(4)
C6 C7 1.397(4)
C6 H3 0.9500
C7 C8 1.381(4)
C7 H4 0.9500
C8 C9 1.395(5)
C8 H2 0.9500
C9 C10 1.386(4)
C9 H5 0.9500
C10 H6 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C3 N1 C1 N2 0.2(3)
C4 N1 C1 N2 179.7(2)
C3 N1 C1 I1 -178.7(2)
C4 N1 C1 I1 0.9(4)
N1 C1 N2 C2 -0.3(3)
I1 C1 N2 C2 178.5(2)
C1 N2 C2 C3 0.3(3)
N2 C2 C3 N1 -0.2(3)
C1 N1 C3 C2 0.1(3)
C4 N1 C3 C2 -179.5(3)
C1 N1 C4 C5 -89.3(3)
C3 N1 C4 C5 90.2(3)
N1 C4 C5 C6 13.0(4)
N1 C4 C5 C10 -167.7(2)
C10 C5 C6 C7 0.8(4)
C4 C5 C6 C7 -179.9(3)
C5 C6 C7 C8 0.0(4)
C6 C7 C8 C9 -0.3(4)
C7 C8 C9 C10 -0.2(4)
C8 C9 C10 C5 1.1(4)
C6 C5 C10 C9 -1.4(4)
C4 C5 C10 C9 179.3(3)
