#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/10/2231062.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_2231062
loop_
_publ_author_name
'Han, Jie'
'Zhang, Jun'
'Yang, Qi'
'Zhao, Ming-gao'
'Fan, Guang'
_publ_section_title
;
 2-Chloromethyl-1-methyl-1,3-benzimidazole
;
_journal_coeditor_code           DN2705
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2104
_journal_paper_doi               10.1107/S1600536811028376
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H9 Cl N2'
_chemical_formula_moiety         'C9 H9 Cl N2'
_chemical_formula_sum            'C9 H9 Cl N2'
_chemical_formula_weight         180.63
_chemical_name_systematic
;
2-Chloromethyl-1-methyl-1,3-benzimidazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.566(3)
_cell_angle_beta                 79.682(4)
_cell_angle_gamma                68.134(4)
_cell_formula_units_Z            2
_cell_length_a                   6.607(2)
_cell_length_b                   8.168(2)
_cell_length_c                   8.925(3)
_cell_measurement_reflns_used    2191
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.32
_cell_volume                     439.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2191
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.9368
_exptl_absorpt_correction_T_min  0.8740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0423
_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/[σ²(Fo²)+(0.0552P)²+0.1656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1361
_reflns_number_total             1523
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2705.cif
_cod_data_source_block           I
_cod_database_code               2231062
_cod_database_fobs_code          2231062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.2259(4) 0.4372(3) 0.6995(2) 0.0610(6) Uani d . 1 1
H H1A 0.3424 0.4781 0.7109 0.073 Uiso calc R 1 1
H H1B 0.0985 0.5393 0.6790 0.073 Uiso calc R 1 1
C C2 0.1665(3) 0.3458(2) 0.8432(2) 0.0498(5) Uani d . 1 1
C C3 -0.2214(4) 0.3954(3) 0.8004(3) 0.0666(6) Uani d . 1 1
H H3A -0.3405 0.3638 0.8563 0.100 Uiso calc PR 0.50 1
H H3B -0.1788 0.3444 0.7017 0.100 Uiso calc PR 0.50 1
H H3C -0.2683 0.5215 0.7888 0.100 Uiso calc PR 0.50 1
H H3D -0.1846 0.4560 0.7082 0.100 Uiso calc PR 0.50 1
H H3E -0.3463 0.4754 0.8628 0.100 Uiso calc PR 0.50 1
H H3F -0.2568 0.2983 0.7757 0.100 Uiso calc PR 0.50 1
C C4 -0.0294(3) 0.2393(2) 1.0212(2) 0.0488(5) Uani d . 1 1
C C5 -0.1859(4) 0.1843(3) 1.1144(3) 0.0600(6) Uani d . 1 1
H H5 -0.3242 0.2069 1.0885 0.072 Uiso calc R 1 1
C C6 -0.1250(4) 0.0947(3) 1.2471(3) 0.0675(6) Uani d . 1 1
H H6 -0.2258 0.0574 1.3137 0.081 Uiso calc R 1 1
C C7 0.0842(4) 0.0581(3) 1.2848(3) 0.0673(6) Uani d . 1 1
H H7 0.1198 -0.0041 1.3751 0.081 Uiso calc R 1 1
C C8 0.2384(4) 0.1119(3) 1.1915(2) 0.0605(6) Uani d . 1 1
H H8 0.3773 0.0871 1.2173 0.073 Uiso calc R 1 1
C C9 0.1803(3) 0.2046(2) 1.0572(2) 0.0495(5) Uani d . 1 1
Cl Cl1 0.31643(17) 0.29247(10) 0.54306(8) 0.1088(4) Uani d . 1 1
N N1 0.3008(3) 0.2749(2) 0.94299(19) 0.0535(4) Uani d . 1 1
N N2 -0.0342(3) 0.3294(2) 0.88264(18) 0.0498(4) Uani d . 1 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 Cl1 110.86(15)
C2 C1 H1A 109.5
Cl1 C1 H1A 109.5
C2 C1 H1B 109.5
Cl1 C1 H1B 109.5
H1A C1 H1B 108.1
N1 C2 N2 114.14(18)
N1 C2 C1 123.36(19)
N2 C2 C1 122.49(18)
N2 C3 H3A 109.5
N2 C3 H3B 109.5
H3A C3 H3B 109.5
N2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N2 C3 H3D 109.5
H3A C3 H3D 141.1
H3B C3 H3D 56.3
H3C C3 H3D 56.3
N2 C3 H3E 109.5
H3A C3 H3E 56.3
H3B C3 H3E 141.1
H3C C3 H3E 56.3
H3D C3 H3E 109.5
N2 C3 H3F 109.5
H3A C3 H3F 56.3
H3B C3 H3F 56.3
H3C C3 H3F 141.1
H3D C3 H3F 109.5
H3E C3 H3F 109.5
N2 C4 C5 131.59(19)
N2 C4 C9 105.69(17)
C5 C4 C9 122.71(19)
C6 C5 C4 116.3(2)
C6 C5 H5 121.9
C4 C5 H5 121.9
C5 C6 C7 121.9(2)
C5 C6 H6 119.1
C7 C6 H6 119.1
C8 C7 C6 121.5(2)
C8 C7 H7 119.3
C6 C7 H7 119.3
C7 C8 C9 117.9(2)
C7 C8 H8 121.1
C9 C8 H8 121.1
C8 C9 N1 130.36(19)
C8 C9 C4 119.77(19)
N1 C9 C4 109.87(17)
C2 N1 C9 104.17(16)
C2 N2 C4 106.13(16)
C2 N2 C3 128.34(18)
C4 N2 C3 125.52(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.488(3)
C1 Cl1 1.786(2)
C1 H1A 0.9700
C1 H1B 0.9700
C2 N1 1.310(3)
C2 N2 1.363(3)
C3 N2 1.453(3)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C3 H3D 0.9600
C3 H3E 0.9600
C3 H3F 0.9600
C4 N2 1.377(3)
C4 C5 1.389(3)
C4 C9 1.398(3)
C5 C6 1.373(3)
C5 H5 0.9300
C6 C7 1.397(4)
C6 H6 0.9300
C7 C8 1.373(3)
C7 H7 0.9300
C8 C9 1.390(3)
C8 H8 0.9300
C9 N1 1.393(3)
