#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/78/2007892.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_2007892
loop_
_publ_author_name
'Elgemeie, Galal E. H.'
'Metwally, Nadia H.'
'Jones, Peter G.'
_publ_section_title
;
 1,2-Dimethylpyrido[1,2-a]benzimidazole-4-carbonitrile
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1871
_journal_page_last               1873
_journal_paper_doi               10.1107/S0108270198008221
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C14 H11 N3'
_chemical_formula_weight         221.26
_chemical_name_systematic
;
1,2-Dimethyl-pyrido[2,1-b]benzimidazole-4-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.469(2)
_cell_length_b                   8.106(2)
_cell_length_c                   18.238(4)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10.0
_cell_volume                     1101.8(5)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992b)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe STADI-4'
_diffrn_measurement_method       ω/θ
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2722
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0631P)²+0.2377P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                1448
_reflns_number_total             1935
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1261.cif
_cod_data_source_block           vorbet
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2007892
_cod_database_fobs_code          2007892
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.2307(2) 0.4811(2) 0.52358(9) 0.0266(4) Uani d . 1 . . N
N2 0.1294(2) 0.2243(2) 0.49023(9) 0.0296(4) Uani d . 1 . . N
C1 0.2983(2) 0.6374(3) 0.51024(11) 0.0288(5) Uani d . 1 . . C
C2 0.3375(3) 0.6783(3) 0.44046(12) 0.0315(5) Uani d . 1 . . C
C3 0.3030(3) 0.5640(3) 0.38293(11) 0.0324(5) Uani d . 1 . . C
H3 0.3287 0.5938 0.3343 0.039 Uiso calc R 1 . . H
C4 0.2334(3) 0.4113(3) 0.39549(11) 0.0315(5) Uani d . 1 . . C
C5 0.0568(3) 0.1342(3) 0.61540(12) 0.0340(5) Uani d . 1 . . C
H5 0.0140 0.0285 0.6001 0.041 Uiso calc R 1 . . H
C6 0.0592(3) 0.1819(3) 0.68801(12) 0.0411(6) Uani d . 1 . . C
H6 0.0166 0.1081 0.7234 0.049 Uiso calc R 1 . . H
C7 0.1233(3) 0.3372(3) 0.71037(12) 0.0432(6) Uani d . 1 . . C
H7 0.1238 0.3661 0.7609 0.052 Uiso calc R 1 . . H
C8 0.1854(3) 0.4491(3) 0.66176(11) 0.0369(6) Uani d . 1 . . C
H8 0.2291 0.5540 0.6777 0.044 Uiso calc R 1 . . H
C9 0.1821(3) 0.4030(3) 0.58794(11) 0.0281(5) Uani d . 1 . . C
C10 0.1195(3) 0.2468(3) 0.56517(11) 0.0287(5) Uani d . 1 . . C
C11 0.1953(2) 0.3651(3) 0.46758(11) 0.0263(5) Uani d . 1 . . C
C12 0.1920(3) 0.2956(3) 0.33753(12) 0.0387(6) Uani d . 1 . . C
C13 0.4099(3) 0.8459(3) 0.42232(14) 0.0441(6) Uani d . 1 . . C
H13A 0.3227 0.9308 0.4338 0.053 Uiso calc R 1 . . H
H13B 0.4312 0.8507 0.3699 0.053 Uiso calc R 1 . . H
H13C 0.5230 0.8651 0.4515 0.053 Uiso calc R 1 . . H
C14 0.3195(3) 0.7521(3) 0.57402(12) 0.0387(6) Uani d . 1 . . C
H14A 0.3617 0.8594 0.5575 0.046 Uiso calc R 1 . . H
H14B 0.4071 0.7065 0.6110 0.046 Uiso calc R 1 . . H
H14C 0.2037 0.7658 0.5956 0.046 Uiso calc R 1 . . H
N3 0.1578(3) 0.2015(3) 0.29170(12) 0.0593(7) Uani d . 1 . . N
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 122.50(17) y
C1 N1 C9 132.41(18) y
C11 N1 C9 105.08(16) y
C11 N2 C10 103.91(17) y
C2 C1 N1 119.10(19) ?
C2 C1 C14 123.95(19) ?
N1 C1 C14 116.93(18) ?
C1 C2 C3 119.6(2) ?
C1 C2 C13 121.7(2) ?
C3 C2 C13 118.6(2) ?
C4 C3 C2 121.5(2) ?
C3 C4 C11 119.81(19) ?
C3 C4 C12 122.4(2) ?
C11 C4 C12 117.81(19) ?
C6 C5 C10 117.6(2) ?
C5 C6 C7 121.0(2) ?
C8 C7 C6 122.1(2) ?
C7 C8 C9 117.5(2) ?
C8 C9 N1 134.2(2) y
C8 C9 C10 120.8(2) y
N1 C9 C10 105.03(17) y
N2 C10 C5 127.1(2) y
N2 C10 C9 111.85(18) y
C5 C10 C9 121.04(19) y
N2 C11 N1 114.13(17) y
N2 C11 C4 128.46(19) y
N1 C11 C4 117.41(18) y
N3 C12 C4 179.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.391(3) y
N1 C11 . 1.401(3) y
N1 C9 . 1.403(3) y
N2 C11 . 1.320(3) y
N2 C10 . 1.386(3) y
C1 C2 . 1.365(3) ?
C1 C14 . 1.489(3) ?
C2 C3 . 1.411(3) ?
C2 C13 . 1.507(3) ?
C3 C4 . 1.368(3) ?
C4 C11 . 1.414(3) ?
C4 C12 . 1.431(3) ?
C5 C6 . 1.379(3) ?
C5 C10 . 1.396(3) ?
C6 C7 . 1.398(3) ?
C7 C8 . 1.370(3) ?
C8 C9 . 1.396(3) ?
C9 C10 . 1.403(3) y
C12 N3 . 1.148(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 N3 2 0.95 2.47 3.405(3) 169.1 y
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
C11 N1 C1 C2 -2.2(3)
C9 N1 C1 C2 178.51(19)
C11 N1 C1 C14 176.47(17)
C9 N1 C1 C14 -2.9(3)
N1 C1 C2 C3 2.2(3)
C14 C1 C2 C3 -176.32(19)
N1 C1 C2 C13 179.58(18)
C14 C1 C2 C13 1.0(3)
C1 C2 C3 C4 -1.0(3)
C13 C2 C3 C4 -178.48(19)
C2 C3 C4 C11 -0.3(3)
C2 C3 C4 C12 177.9(2)
C10 C5 C6 C7 -0.4(3)
C5 C6 C7 C8 0.4(4)
C6 C7 C8 C9 0.3(3)
C7 C8 C9 N1 179.2(2)
C7 C8 C9 C10 -0.9(3)
C1 N1 C9 C8 -1.3(4)
C11 N1 C9 C8 179.3(2)
C1 N1 C9 C10 178.76(18)
C11 N1 C9 C10 -0.65(19)
C11 N2 C10 C5 179.5(2)
C11 N2 C10 C9 -0.6(2)
C6 C5 C10 N2 179.81(19)
C6 C5 C10 C9 -0.2(3)
C8 C9 C10 N2 -179.16(18)
N1 C9 C10 N2 0.8(2)
C8 C9 C10 C5 0.8(3)
N1 C9 C10 C5 -179.24(18)
C10 N2 C11 N1 0.1(2)
C10 N2 C11 C4 -179.9(2)
C1 N1 C11 N2 -179.13(16)
C9 N1 C11 N2 0.3(2)
C1 N1 C11 C4 0.8(3)
C9 N1 C11 C4 -179.67(17)
C3 C4 C11 N2 -179.64(19)
C12 C4 C11 N2 2.0(3)
C3 C4 C11 N1 0.4(3)
C12 C4 C11 N1 -177.93(18)
C3 C4 C12 N3 -17E1(10)
C11 C4 C12 N3 5(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136750
