#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/69/2236902.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_2236902
loop_
_publ_author_name
'de Jager, Josephus Jacobus'
'Smith, Vincent J.'
_publ_section_title
;
 1-[(1-Methyl-1H-imidazol-5-yl)methyl]-1H-indole-5-carbonitrile
;
_journal_coeditor_code           HB7000
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3486
_journal_paper_doi               10.1107/S1600536812048404
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C14 H12 N4'
_chemical_formula_sum            'C14 H12 N4'
_chemical_formula_weight         236.28
_chemical_name_common            Cyano-Indole
_chemical_name_systematic
;
1-[(1-Methyl-1H-imidazol-5-yl)methyl]-1H-indole-5-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.727(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9624(16)
_cell_length_b                   7.8687(12)
_cell_length_c                   14.292(2)
_cell_measurement_reflns_used    7965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.59
_cell_measurement_theta_min      2.98
_cell_volume                     1180.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'X-SEED (Barbour, 2001; Atwood et al., 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36857
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.84
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0422
_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)+(0.0451P)²+0.6130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2643
_reflns_number_total             3286
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7000.cif
_cod_data_source_block           I
_cod_original_cell_volume        1180.6(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2236902
_cod_database_fobs_code          2236902
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_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
N N1 0.74899(9) 0.05550(13) 0.10401(7) 0.0182(2) Uani d . 1 1
C C8 0.63632(11) 0.14156(15) 0.06741(8) 0.0172(2) Uani d . 1 1
C C3 0.57779(11) 0.15677(15) 0.14387(8) 0.0182(2) Uani d . 1 1
N N3 1.05057(10) 0.09402(14) 0.16447(8) 0.0204(2) Uani d . 1 1
N N4 1.15865(10) -0.14899(14) 0.18381(8) 0.0218(2) Uani d . 1 1
C C6 0.46523(12) 0.28892(17) -0.04359(9) 0.0222(3) Uani d . 1 1
H H6 0.4248 0.3338 -0.1066 0.027 Uiso calc R 1 1
C C9 0.28834(12) 0.40021(18) 0.01344(10) 0.0253(3) Uani d . 1 1
C C13 1.16216(12) 0.01364(17) 0.20734(9) 0.0213(3) Uani d . 1 1
H H13 1.2346 0.0681 0.2495 0.026 Uiso calc R 1 1
C C2 0.66051(12) 0.07444(16) 0.22788(9) 0.0202(2) Uani d . 1 1
H H2 0.6472 0.0638 0.2904 0.024 Uiso calc R 1 1
N N2 0.19352(11) 0.47248(17) -0.00085(10) 0.0327(3) Uani d . 1 1
C C4 0.46133(12) 0.24195(16) 0.12543(9) 0.0206(3) Uani d . 1 1
H H4 0.4203 0.2545 0.1752 0.025 Uiso calc R 1 1
C C1 0.76221(12) 0.01428(16) 0.20058(9) 0.0201(2) Uani d . 1 1
H H1 0.8318 -0.0469 0.2419 0.024 Uiso calc R 1 1
C C12 1.03687(12) -0.17490(17) 0.12259(9) 0.0209(3) Uani d . 1 1
H H12 1.0050 -0.2807 0.0937 0.025 Uiso calc R 1 1
C C7 0.58051(11) 0.20564(16) -0.02668(9) 0.0201(2) Uani d . 1 1
H H7 0.6205 0.1923 -0.0770 0.024 Uiso calc R 1 1
C C5 0.40688(11) 0.30803(16) 0.03208(9) 0.0213(3) Uani d . 1 1
C C10 0.83783(11) 0.01570(18) 0.04742(9) 0.0214(3) Uani d . 1 1
H H10A 0.8426 0.1144 0.0056 0.026 Uiso calc R 1 1
H H10B 0.8041 -0.0819 0.0039 0.026 Uiso calc R 1 1
C C11 0.96882(11) -0.02628(16) 0.10955(9) 0.0195(2) Uani d . 1 1
C C14 1.02309(13) 0.27356(18) 0.17436(11) 0.0296(3) Uani d . 1 1
H H14A 1.0997 0.3305 0.2147 0.044 Uiso calc R 1 1
H H14C 0.9546 0.2842 0.2054 0.044 Uiso calc R 1 1
H H14B 0.9965 0.3265 0.1096 0.044 Uiso calc R 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 108.65(10)
C8 N1 C10 124.20(10)
C1 N1 C10 127.14(10)
N1 C8 C7 129.75(11)
N1 C8 C3 107.70(10)
C7 C8 C3 122.55(11)
C4 C3 C8 119.00(11)
C4 C3 C2 134.22(11)
C8 C3 C2 106.78(10)
C13 N3 C11 106.87(11)
C13 N3 C14 126.29(11)
C11 N3 C14 126.84(11)
C13 N4 C12 104.82(11)
C7 C6 C5 120.60(11)
C7 C6 H6 119.7
C5 C6 H6 119.7
N2 C9 C5 179.32(16)
N4 C13 N3 112.35(11)
N4 C13 H13 123.8
N3 C13 H13 123.8
C1 C2 C3 106.77(11)
C1 C2 H2 126.6
C3 C2 H2 126.6
C5 C4 C3 118.35(11)
C5 C4 H4 120.8
C3 C4 H4 120.8
C2 C1 N1 110.09(11)
C2 C1 H1 125.0
N1 C1 H1 125.0
C11 C12 N4 110.39(11)
C11 C12 H12 124.8
N4 C12 H12 124.8
C6 C7 C8 117.60(11)
C6 C7 H7 121.2
C8 C7 H7 121.2
C4 C5 C6 121.89(11)
C4 C5 C9 118.55(12)
C6 C5 C9 119.56(12)
N1 C10 C11 113.39(10)
N1 C10 H10A 108.9
C11 C10 H10A 108.9
N1 C10 H10B 108.9
C11 C10 H10B 108.9
H10A C10 H10B 107.7
C12 C11 N3 105.58(11)
C12 C11 C10 131.51(12)
N3 C11 C10 122.82(11)
N3 C14 H14A 109.5
N3 C14 H14C 109.5
H14A C14 H14C 109.5
N3 C14 H14B 109.5
H14A C14 H14B 109.5
H14C C14 H14B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.3733(15)
N1 C1 1.3842(15)
N1 C10 1.4676(15)
C8 C7 1.4011(16)
C8 C3 1.4226(16)
C3 C4 1.3982(17)
C3 C2 1.4341(17)
N3 C13 1.3567(16)
N3 C11 1.3822(16)
N3 C14 1.4598(17)
N4 C13 1.3209(17)
N4 C12 1.3845(16)
C6 C7 1.3817(17)
C6 C5 1.4140(18)
C6 H6 0.9500
C9 N2 1.1504(18)
C9 C5 1.4445(18)
C13 H13 0.9500
C2 C1 1.3673(17)
C2 H2 0.9500
C4 C5 1.3958(18)
C4 H4 0.9500
C1 H1 0.9500
C12 C11 1.3707(18)
C12 H12 0.9500
C7 H7 0.9500
C10 C11 1.4918(17)
C10 H10A 0.9900
C10 H10B 0.9900
C14 H14A 0.9800
C14 H14C 0.9800
C14 H14B 0.9800
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
C4 H4 N4 2_655 0.95 2.53 3.4588(18) 167
C13 H13 N4 2_755 0.95 2.57 3.4010(18) 147
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
C1 N1 C8 C7 -178.49(12)
C10 N1 C8 C7 1.3(2)
C1 N1 C8 C3 0.78(13)
C10 N1 C8 C3 -179.46(11)
N1 C8 C3 C4 179.29(11)
C7 C8 C3 C4 -1.37(18)
N1 C8 C3 C2 -0.42(13)
C7 C8 C3 C2 178.91(11)
C12 N4 C13 N3 -0.46(14)
C11 N3 C13 N4 0.31(14)
C14 N3 C13 N4 -179.36(12)
C4 C3 C2 C1 -179.75(14)
C8 C3 C2 C1 -0.09(14)
C8 C3 C4 C5 0.32(17)
C2 C3 C4 C5 179.95(13)
C3 C2 C1 N1 0.58(14)
C8 N1 C1 C2 -0.86(14)
C10 N1 C1 C2 179.39(11)
C13 N4 C12 C11 0.44(14)
C5 C6 C7 C8 0.08(18)
N1 C8 C7 C6 -179.67(12)
C3 C8 C7 C6 1.15(18)
C3 C4 C5 C6 0.89(18)
C3 C4 C5 C9 -178.31(11)
C7 C6 C5 C4 -1.11(19)
C7 C6 C5 C9 178.07(12)
C8 N1 C10 C11 161.26(11)
C1 N1 C10 C11 -19.02(18)
N4 C12 C11 N3 -0.26(14)
N4 C12 C11 C10 176.39(12)
C13 N3 C11 C12 -0.02(13)
C14 N3 C11 C12 179.65(12)
C13 N3 C11 C10 -177.03(11)
C14 N3 C11 C10 2.63(19)
N1 C10 C11 C12 112.73(15)
N1 C10 C11 N3 -71.12(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658225
