#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230776.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_2230776
loop_
_publ_author_name
'Deng, Xiang'
'Wu, Di'
'Huang, Xiaomei'
'Luo, Feihua'
_publ_section_title
;
 4-[Bis(1H-indol-3-yl)methyl]benzonitrile
;
_journal_coeditor_code           LH5252
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1603
_journal_paper_doi               10.1107/S1600536811020411
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C24 H17 N3'
_chemical_formula_moiety         'C24 H17 N3'
_chemical_formula_sum            'C24 H17 N3'
_chemical_formula_weight         347.41
_chemical_name_systematic
;
4-[Bis(1H-indol-3-yl)methyl]benzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.562(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5882(12)
_cell_length_b                   19.155(3)
_cell_length_c                   10.3801(13)
_cell_measurement_reflns_used    3543
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.86
_cell_volume                     1874.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14081
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.134
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0410
_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)+(0.0494P)²+0.3483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2613
_reflns_number_total             3292
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5252.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230776
_cod_database_fobs_code          2230776
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.58636(15) 0.10803(8) 0.05439(14) 0.0403(4) Uani d . 1 1 . .
H H1 0.5637 0.0581 0.0542 0.048 Uiso calc R 1 1 . .
C C2 0.62867(15) 0.12277(7) -0.07541(15) 0.0403(4) Uani d . 1 1 . .
C C3 0.54762(15) 0.10350(8) -0.20061(15) 0.0421(4) Uani d . 1 1 . .
C C4 0.41722(17) 0.06995(9) -0.23996(16) 0.0520(4) Uani d . 1 1 . .
H H4 0.3633 0.0566 -0.1782 0.062 Uiso calc R 1 1 . .
C C5 0.3700(2) 0.05705(10) -0.37001(18) 0.0652(5) Uani d . 1 1 . .
H H5 0.2839 0.0342 -0.3963 0.078 Uiso calc R 1 1 . .
C C6 0.4482(2) 0.07750(11) -0.46368(19) 0.0690(5) Uani d . 1 1 . .
H H6 0.4132 0.0685 -0.5517 0.083 Uiso calc R 1 1 . .
C C7 0.5762(2) 0.11079(10) -0.42865(17) 0.0627(5) Uani d . 1 1 . .
H H7 0.6286 0.1242 -0.4915 0.075 Uiso calc R 1 1 . .
C C8 0.62532(16) 0.12383(8) -0.29631(16) 0.0467(4) Uani d . 1 1 . .
C C9 0.74842(16) 0.15361(8) -0.10002(17) 0.0477(4) Uani d . 1 1 . .
H H9 0.8208 0.1714 -0.0365 0.057 Uiso calc R 1 1 . .
C C10 0.70384(15) 0.11951(8) 0.16965(15) 0.0419(4) Uani d . 1 1 . .
C C11 0.82977(15) 0.07764(8) 0.20221(15) 0.0425(4) Uani d . 1 1 . .
C C12 0.88333(17) 0.02088(9) 0.14286(17) 0.0526(4) Uani d . 1 1 . .
H H12 0.8366 0.0042 0.0623 0.063 Uiso calc R 1 1 . .
C C13 1.00687(19) -0.01001(10) 0.2058(2) 0.0657(5) Uani d . 1 1 . .
H H13 1.0432 -0.0481 0.1674 0.079 Uiso calc R 1 1 . .
C C14 1.0784(2) 0.01494(11) 0.3263(2) 0.0686(5) Uani d . 1 1 . .
H H14 1.1610 -0.0073 0.3671 0.082 Uiso calc R 1 1 . .
C C15 1.02992(19) 0.07111(11) 0.38510(18) 0.0624(5) Uani d . 1 1 . .
H H15 1.0783 0.0878 0.4650 0.075 Uiso calc R 1 1 . .
C C16 0.90608(16) 0.10251(9) 0.32187(15) 0.0496(4) Uani d . 1 1 . .
C C17 0.71121(17) 0.16730(9) 0.26731(16) 0.0517(4) Uani d . 1 1 . .
H H17 0.6434 0.2015 0.2715 0.062 Uiso calc R 1 1 . .
C C18 0.45208(15) 0.14628(8) 0.07105(15) 0.0422(4) Uani d . 1 1 . .
C C19 0.42852(19) 0.21445(10) 0.0326(2) 0.0742(6) Uani d . 1 1 . .
H H19 0.4949 0.2373 -0.0072 0.089 Uiso calc R 1 1 . .
C C20 0.3091(2) 0.24975(10) 0.0516(2) 0.0786(7) Uani d . 1 1 . .
H H20 0.2961 0.2962 0.0262 0.094 Uiso calc R 1 1 . .
C C21 0.20928(16) 0.21613(9) 0.10831(17) 0.0528(4) Uani d . 1 1 . .
C C22 0.23052(18) 0.14779(10) 0.14648(19) 0.0647(5) Uani d . 1 1 . .
H H22 0.1631 0.1246 0.1846 0.078 Uiso calc R 1 1 . .
C C23 0.35136(17) 0.11352(9) 0.12836(17) 0.0569(5) Uani d . 1 1 . .
H H23 0.3653 0.0673 0.1554 0.068 Uiso calc R 1 1 . .
C C24 0.08275(18) 0.25223(10) 0.12602(18) 0.0602(5) Uani d . 1 1 . .
N N1 -0.01856(16) 0.28075(10) 0.13748(17) 0.0757(5) Uani d . 1 1 . .
N N2 0.83216(15) 0.15817(8) 0.35857(15) 0.0585(4) Uani d . 1 1 . .
H H2A 0.856(2) 0.1831(12) 0.434(2) 0.088(7) Uiso d . 1 1 . .
N N3 0.74724(15) 0.15470(7) -0.23225(15) 0.0539(4) Uani d . 1 1 . .
H H3A 0.814(2) 0.1722(10) -0.2680(19) 0.069(6) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 C1 C2 . . 113.60(12) ?
C10 C1 C18 . . 111.50(12) ?
C2 C1 C18 . . 112.65(12) ?
C10 C1 H1 . . 106.1 ?
C2 C1 H1 . . 106.1 ?
C18 C1 H1 . . 106.1 ?
C9 C2 C3 . . 106.14(13) ?
C9 C2 C1 . . 128.86(14) ?
C3 C2 C1 . . 124.97(13) ?
C4 C3 C8 . . 118.91(15) ?
C4 C3 C2 . . 133.59(14) ?
C8 C3 C2 . . 107.49(13) ?
C5 C4 C3 . . 119.26(16) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 121.14(18) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 C5 . . 121.16(18) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 C8 . . 118.03(17) ?
C6 C7 H7 . . 121.0 ?
C8 C7 H7 . . 121.0 ?
N3 C8 C7 . . 131.44(16) ?
N3 C8 C3 . . 107.05(14) ?
C7 C8 C3 . . 121.50(16) ?
C2 C9 N3 . . 110.08(15) ?
C2 C9 H9 . . 125.0 ?
N3 C9 H9 . . 125.0 ?
C17 C10 C11 . . 105.91(14) ?
C17 C10 C1 . . 128.49(14) ?
C11 C10 C1 . . 125.50(13) ?
C12 C11 C16 . . 118.77(14) ?
C12 C11 C10 . . 133.90(15) ?
C16 C11 C10 . . 107.31(14) ?
C13 C12 C11 . . 118.70(17) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 121.11(18) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C15 C14 C13 . . 121.38(17) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 117.70(17) ?
C14 C15 H15 . . 121.2 ?
C16 C15 H15 . . 121.2 ?
N2 C16 C15 . . 130.37(17) ?
N2 C16 C11 . . 107.29(14) ?
C15 C16 C11 . . 122.30(17) ?
C10 C17 N2 . . 110.63(15) ?
C10 C17 H17 . . 124.7 ?
N2 C17 H17 . . 124.7 ?
C19 C18 C23 . . 117.96(14) ?
C19 C18 C1 . . 121.60(13) ?
C23 C18 C1 . . 120.43(14) ?
C18 C19 C20 . . 121.58(16) ?
C18 C19 H19 . . 119.2 ?
C20 C19 H19 . . 119.2 ?
C21 C20 C19 . . 119.69(17) ?
C21 C20 H20 . . 120.2 ?
C19 C20 H20 . . 120.2 ?
C22 C21 C20 . . 119.55(15) ?
C22 C21 C24 . . 120.41(16) ?
C20 C21 C24 . . 120.04(16) ?
C21 C22 C23 . . 120.03(15) ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C22 C23 C18 . . 121.19(16) ?
C22 C23 H23 . . 119.4 ?
C18 C23 H23 . . 119.4 ?
N1 C24 C21 . . 178.7(2) ?
C17 N2 C16 . . 108.82(14) ?
C17 N2 H2A . . 125.3(14) ?
C16 N2 H2A . . 125.7(14) ?
C8 N3 C9 . . 109.24(13) ?
C8 N3 H3A . . 126.3(13) ?
C9 N3 H3A . . 124.4(13) ?
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
C1 C10 . 1.502(2) ?
C1 C2 . 1.503(2) ?
C1 C18 . 1.519(2) ?
C1 H1 . 0.9800 ?
C2 C9 . 1.356(2) ?
C2 C3 . 1.435(2) ?
C3 C4 . 1.399(2) ?
C3 C8 . 1.402(2) ?
C4 C5 . 1.366(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.371(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.391(2) ?
C7 H7 . 0.9300 ?
C8 N3 . 1.369(2) ?
C9 N3 . 1.371(2) ?
C9 H9 . 0.9300 ?
C10 C17 . 1.358(2) ?
C10 C11 . 1.437(2) ?
C11 C12 . 1.393(2) ?
C11 C16 . 1.404(2) ?
C12 C13 . 1.377(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.396(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.361(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.384(2) ?
C15 H15 . 0.9300 ?
C16 N2 . 1.372(2) ?
C17 N2 . 1.368(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.372(2) ?
C18 C23 . 1.375(2) ?
C19 C20 . 1.375(2) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.373(2) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.372(2) ?
C21 C24 . 1.437(2) ?
C22 C23 . 1.374(2) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C24 N1 . 1.140(2) ?
N2 H2A . 0.91(2) ?
N3 H3A . 0.86(2) ?
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
N3 H3A N1 4_665 0.86(2) 2.22(2) 3.084(2) 178.6(18)
N2 H2A N1 4_666 0.91(2) 2.34(2) 3.206(2) 160.3(19)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C9 . . . . -10.3(2) ?
C18 C1 C2 C9 . . . . 117.73(17) ?
C10 C1 C2 C3 . . . . 167.30(13) ?
C18 C1 C2 C3 . . . . -64.69(18) ?
C9 C2 C3 C4 . . . . 179.30(17) ?
C1 C2 C3 C4 . . . . 1.3(3) ?
C9 C2 C3 C8 . . . . 0.43(16) ?
C1 C2 C3 C8 . . . . -177.61(13) ?
C8 C3 C4 C5 . . . . 0.9(2) ?
C2 C3 C4 C5 . . . . -177.91(16) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
C4 C5 C6 C7 . . . . 0.6(3) ?
C5 C6 C7 C8 . . . . -0.3(3) ?
C6 C7 C8 N3 . . . . 179.15(17) ?
C6 C7 C8 C3 . . . . 0.3(3) ?
C4 C3 C8 N3 . . . . -179.68(14) ?
C2 C3 C8 N3 . . . . -0.62(17) ?
C4 C3 C8 C7 . . . . -0.6(2) ?
C2 C3 C8 C7 . . . . 178.47(14) ?
C3 C2 C9 N3 . . . . -0.08(17) ?
C1 C2 C9 N3 . . . . 177.86(14) ?
C2 C1 C10 C17 . . . . 115.39(17) ?
C18 C1 C10 C17 . . . . -13.2(2) ?
C2 C1 C10 C11 . . . . -68.78(18) ?
C18 C1 C10 C11 . . . . 162.63(13) ?
C17 C10 C11 C12 . . . . 179.63(17) ?
C1 C10 C11 C12 . . . . 3.0(3) ?
C17 C10 C11 C16 . . . . 1.12(17) ?
C1 C10 C11 C16 . . . . -175.49(14) ?
C16 C11 C12 C13 . . . . 2.0(2) ?
C10 C11 C12 C13 . . . . -176.41(16) ?
C11 C12 C13 C14 . . . . -0.5(3) ?
C12 C13 C14 C15 . . . . -0.8(3) ?
C13 C14 C15 C16 . . . . 0.5(3) ?
C14 C15 C16 N2 . . . . 178.63(17) ?
C14 C15 C16 C11 . . . . 1.1(2) ?
C12 C11 C16 N2 . . . . 179.62(14) ?
C10 C11 C16 N2 . . . . -1.61(17) ?
C12 C11 C16 C15 . . . . -2.3(2) ?
C10 C11 C16 C15 . . . . 176.45(14) ?
C11 C10 C17 N2 . . . . -0.21(18) ?
C1 C10 C17 N2 . . . . 176.26(14) ?
C10 C1 C18 C19 . . . . 87.1(2) ?
C2 C1 C18 C19 . . . . -42.0(2) ?
C10 C1 C18 C23 . . . . -91.44(18) ?
C2 C1 C18 C23 . . . . 139.46(16) ?
C23 C18 C19 C20 . . . . 0.7(3) ?
C1 C18 C19 C20 . . . . -177.84(19) ?
C18 C19 C20 C21 . . . . -1.1(4) ?
C19 C20 C21 C22 . . . . 0.6(3) ?
C19 C20 C21 C24 . . . . -178.70(19) ?
C20 C21 C22 C23 . . . . 0.2(3) ?
C24 C21 C22 C23 . . . . 179.56(18) ?
C21 C22 C23 C18 . . . . -0.6(3) ?
C19 C18 C23 C22 . . . . 0.2(3) ?
C1 C18 C23 C22 . . . . 178.74(16) ?
C10 C17 N2 C16 . . . . -0.81(19) ?
C15 C16 N2 C17 . . . . -176.35(17) ?
C11 C16 N2 C17 . . . . 1.50(18) ?
C7 C8 N3 C9 . . . . -178.39(17) ?
C3 C8 N3 C9 . . . . 0.58(17) ?
C2 C9 N3 C8 . . . . -0.32(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9362191
