#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2224576.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_2224576
loop_
_publ_author_name
'Wang, Fang-Ming'
_publ_section_title
;
1-Methyl-4-(1-methyl-1H-benzimidazol-2-yl)pyridinium iodide
;
_journal_coeditor_code BX2252
_journal_issue 1
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o198
_journal_volume 66
_journal_year 2010
_chemical_formula_iupac 'C14 H14 N3 +, I -'
_chemical_formula_moiety 'C14 H14 N3 +, I -'
_chemical_formula_sum 'C14 H14 I N3'
_chemical_formula_weight 351.18
_chemical_name_systematic
;
1-Methyl-4-(1-methyl-1H-benzimidazol-2-yl)pyridinium iodide
;
_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 64.888(3)
_cell_angle_beta 72.933(3)
_cell_angle_gamma 76.394(4)
_cell_formula_units_Z 2
_cell_length_a 7.7048(15)
_cell_length_b 9.9264(18)
_cell_length_c 10.1772(19)
_cell_measurement_reflns_used 1236
_cell_measurement_temperature 291(2)
_cell_measurement_theta_max 22.09
_cell_measurement_theta_min 3.12
_cell_volume 668.2(2)
_computing_cell_refinement 'SAINT (Bruker, 2000)'
_computing_data_collection 'SMART (Bruker, 2000)'
_computing_data_reduction 'SAINT (Bruker, 2000)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature 291(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type 'Bruker SMART CCD area-detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0584
_diffrn_reflns_av_sigmaI/netI 0.0776
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 3353
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 2.27
_exptl_absorpt_coefficient_mu 2.382
_exptl_absorpt_correction_T_max 0.887
_exptl_absorpt_correction_T_min 0.493
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2000)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.745
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description piece
_exptl_crystal_F_000 344
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.944
_refine_diff_density_min -0.484
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 163
_refine_ls_number_reflns 2307
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.000
_refine_ls_R_factor_all 0.0529
_refine_ls_R_factor_gt 0.0434
_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^)+(0.0301P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0898
_refine_ls_wR_factor_ref 0.0918
_reflns_number_gt 1840
_reflns_number_total 2307
_reflns_threshold_expression I>2sigma(I)
_[local]_cod_data_source_file bx2252.cif
_[local]_cod_data_source_block I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_database_code 2224576
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
C C1 0.7976(9) 0.1720(7) 0.3724(7) 0.0574(18) Uani d . 1
H H1A 0.7850 0.1418 0.4774 0.086 Uiso calc R 1
H H1B 0.9149 0.1293 0.3311 0.086 Uiso calc R 1
H H1C 0.7027 0.1374 0.3557 0.086 Uiso calc R 1
C C2 0.7960(8) 0.4044(7) 0.1519(7) 0.0443(15) Uani d . 1
H H2A 0.8121 0.3452 0.0977 0.053 Uiso calc R 1
C C3 0.7870(8) 0.5551(6) 0.0807(7) 0.0422(15) Uani d . 1
H H3A 0.7948 0.5992 -0.0214 0.051 Uiso calc R 1
C C4 0.7660(8) 0.6442(6) 0.1610(6) 0.0387(14) Uani d . 1
C C5 0.7505(8) 0.5736(6) 0.3135(6) 0.0422(15) Uani d . 1
H H5A 0.7337 0.6297 0.3707 0.051 Uiso calc R 1
C C6 0.7598(8) 0.4226(7) 0.3784(7) 0.0445(15) Uani d . 1
H H6A 0.7506 0.3759 0.4806 0.053 Uiso calc R 1
C C7 0.7700(8) 0.8070(6) 0.0779(6) 0.0339(13) Uani d . 1
C C8 0.8426(8) 1.0150(6) -0.0938(6) 0.0395(14) Uani d . 1
C C9 0.9152(8) 1.1306(7) -0.2232(7) 0.0443(15) Uani d . 1
H H9A 1.0063 1.1104 -0.2983 0.053 Uiso calc R 1
C C10 0.8473(9) 1.2748(7) -0.2354(7) 0.0498(17) Uani d . 1
H H10A 0.8941 1.3536 -0.3202 0.060 Uiso calc R 1
C C11 0.7082(9) 1.3076(7) -0.1230(7) 0.0482(16) Uani d . 1
H H11A 0.6644 1.4071 -0.1361 0.058 Uiso calc R 1
C C12 0.6369(8) 1.1955(6) 0.0047(7) 0.0423(15) Uani d . 1
H H12A 0.5454 1.2161 0.0793 0.051 Uiso calc R 1
C C13 0.7076(7) 1.0494(6) 0.0175(6) 0.0344(13) Uani d . 1
C C14 0.5260(8) 0.8957(7) 0.2645(7) 0.0478(16) Uani d . 1
H H14A 0.5225 0.7909 0.3245 0.072 Uiso calc R 1
H H14B 0.4090 0.9405 0.2400 0.072 Uiso calc R 1
H H14C 0.5541 0.9438 0.3187 0.072 Uiso calc R 1
I I1 0.26309(6) 0.26836(5) 0.37099(4) 0.05037(19) Uani d . 1
N N1 0.7821(6) 0.3387(5) 0.2996(6) 0.0432(12) Uani d . 1
N N2 0.8779(7) 0.8606(5) -0.0548(5) 0.0426(12) Uani d . 1
N N3 0.6668(6) 0.9141(5) 0.1277(5) 0.0367(11) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.062(5) 0.042(4) 0.064(5) -0.010(3) -0.008(4) -0.019(3)
C2 0.047(4) 0.049(4) 0.045(4) -0.011(3) -0.011(3) -0.023(3)
C3 0.043(4) 0.046(4) 0.042(4) 0.001(3) -0.011(3) -0.022(3)
C4 0.030(3) 0.047(4) 0.042(4) -0.001(3) -0.008(3) -0.021(3)
C5 0.046(4) 0.045(4) 0.042(4) -0.010(3) -0.007(3) -0.022(3)
C6 0.053(4) 0.044(4) 0.037(3) -0.004(3) -0.008(3) -0.018(3)
C7 0.032(3) 0.039(3) 0.033(3) -0.005(3) -0.008(3) -0.016(3)
C8 0.043(4) 0.042(4) 0.039(3) -0.006(3) -0.016(3) -0.016(3)
C9 0.045(4) 0.046(4) 0.043(4) -0.011(3) -0.010(3) -0.016(3)
C10 0.052(4) 0.051(4) 0.046(4) -0.020(3) -0.021(3) -0.005(3)
C11 0.048(4) 0.038(4) 0.065(5) -0.001(3) -0.024(4) -0.021(3)
C12 0.041(4) 0.044(4) 0.048(4) 0.001(3) -0.013(3) -0.024(3)
C13 0.032(3) 0.041(4) 0.036(3) -0.003(3) -0.014(3) -0.017(3)
C14 0.042(4) 0.047(4) 0.053(4) -0.004(3) -0.008(3) -0.021(3)
I1 0.0493(3) 0.0535(3) 0.0478(3) -0.0021(2) -0.0128(2) -0.0197(2)
N1 0.034(3) 0.039(3) 0.057(3) -0.003(2) -0.013(3) -0.017(3)
N2 0.045(3) 0.046(3) 0.044(3) -0.006(2) -0.014(3) -0.021(2)
N3 0.031(3) 0.045(3) 0.038(3) -0.004(2) -0.009(2) -0.020(3)
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 121.1(5)
N1 C2 H2A 119.5
C3 C2 H2A 119.5
C2 C3 C4 119.7(6)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 118.0(5)
C5 C4 C7 123.9(5)
C3 C4 C7 118.1(5)
C6 C5 C4 119.6(5)
C6 C5 H5A 120.2
C4 C5 H5A 120.2
N1 C6 C5 121.8(6)
N1 C6 H6A 119.1
C5 C6 H6A 119.1
N2 C7 N3 114.0(5)
N2 C7 C4 121.4(5)
N3 C7 C4 124.6(5)
N2 C8 C13 110.2(5)
N2 C8 C9 130.0(6)
C13 C8 C9 119.8(5)
C10 C9 C8 117.4(6)
C10 C9 H9A 121.3
C8 C9 H9A 121.3
C9 C10 C11 122.1(6)
C9 C10 H10A 119.0
C11 C10 H10A 119.0
C12 C11 C10 121.1(6)
C12 C11 H11A 119.5
C10 C11 H11A 119.5
C11 C12 C13 116.7(6)
C11 C12 H12A 121.6
C13 C12 H12A 121.6
N3 C13 C12 131.6(5)
N3 C13 C8 105.5(5)
C12 C13 C8 122.9(6)
N3 C14 H14A 109.5
N3 C14 H14B 109.5
H14A C14 H14B 109.5
N3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C6 N1 C2 119.9(5)
C6 N1 C1 121.0(5)
C2 N1 C1 119.1(5)
C7 N2 C8 103.7(5)
C7 N3 C13 106.5(5)
C7 N3 C14 128.7(5)
C13 N3 C14 124.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.490(8)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N1 1.343(7)
C2 C3 1.353(8)
C2 H2A 0.9300
C3 C4 1.395(7)
C3 H3A 0.9300
C4 C5 1.386(7)
C4 C7 1.475(8)
C5 C6 1.350(7)
C5 H5A 0.9300
C6 N1 1.336(7)
C6 H6A 0.9300
C7 N2 1.318(7)
C7 N3 1.357(7)
C8 N2 1.389(7)
C8 C13 1.397(8)
C8 C9 1.397(8)
C9 C10 1.368(8)
C9 H9A 0.9300
C10 C11 1.412(9)
C10 H10A 0.9300
C11 C12 1.368(8)
C11 H11A 0.9300
C12 C13 1.388(7)
C12 H12A 0.9300
C13 N3 1.369(7)
C14 N3 1.462(7)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
N1 C2 C3 C4 1.1(9)
C2 C3 C4 C5 -1.6(9)
C2 C3 C4 C7 175.7(5)
C3 C4 C5 C6 1.3(9)
C7 C4 C5 C6 -175.7(5)
C4 C5 C6 N1 -0.6(9)
C5 C4 C7 N2 141.4(6)
C3 C4 C7 N2 -35.7(8)
C5 C4 C7 N3 -38.7(8)
C3 C4 C7 N3 144.2(5)
N2 C8 C9 C10 176.4(5)
C13 C8 C9 C10 -0.8(8)
C8 C9 C10 C11 -0.4(8)
C9 C10 C11 C12 0.9(9)
C10 C11 C12 C13 -0.1(8)
C11 C12 C13 N3 -179.4(5)
C11 C12 C13 C8 -1.2(8)
N2 C8 C13 N3 2.6(6)
C9 C8 C13 N3 -179.7(5)
N2 C8 C13 C12 -176.0(5)
C9 C8 C13 C12 1.7(8)
C5 C6 N1 C2 0.1(9)
C5 C6 N1 C1 178.2(6)
C3 C2 N1 C6 -0.3(9)
C3 C2 N1 C1 -178.5(6)
N3 C7 N2 C8 0.4(6)
C4 C7 N2 C8 -179.7(5)
C13 C8 N2 C7 -1.9(6)
C9 C8 N2 C7 -179.3(6)
N2 C7 N3 C13 1.2(6)
C4 C7 N3 C13 -178.7(5)
N2 C7 N3 C14 176.0(5)
C4 C7 N3 C14 -3.8(8)
C12 C13 N3 C7 176.2(5)
C8 C13 N3 C7 -2.2(5)
C12 C13 N3 C14 1.1(9)
C8 C13 N3 C14 -177.3(5)