data_2008049
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  75
_journal_page_last  78
_publ_section_title
;
N-H...\p(Indole) intermolecular interactions in
3,3'-benzylidenediindole
;
loop_
_publ_author_name
  'R. Krishna'
  'D. Velmurugan'
  'G. Babu'
  'P.T. Perumal'
_chemical_formula_sum  'C23 H18 N2'
_chemical_formula_weight  322.39
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  10.1867(10)
_cell_length_b  9.759(2)
_cell_length_c  17.7778(10)
_cell_angle_alpha  90.0000(10)
_cell_angle_beta  94.009(10)
_cell_angle_gamma  90.00(2)
_cell_volume  1763.1(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.215
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0532
_refine_ls_wR_factor_obs  0.1618
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  N1 0.7512(2) 0.2724(2) -0.14979(9) 0.0787(5) Uani d . 1 . N
  H1 0.7349(2) 0.3144(2) -0.19195(9) 0.094 Uiso calc R 1 . H
  C2 0.7426(2) 0.3288(2) -0.07981(11) 0.0676(5) Uani d . 1 . C
  H2 0.7200(2) 0.4194(2) -0.07082(11) 0.081 Uiso calc R 1 . H
  C3 0.7715(2) 0.2344(2) -0.02572(9) 0.0529(4) Uani d . 1 . C
  C4 0.8374(2) -0.0222(2) -0.04090(13) 0.0660(5) Uani d . 1 . C
  H4 0.8465(2) -0.0441(2) 0.01011(13) 0.079 Uiso calc R 1 . H
  C5 0.8580(2) -0.1197(2) -0.0951(2) 0.0832(7) Uani d . 1 . C
  H5 0.8799(2) -0.2086(2) -0.0801(2) 0.100 Uiso calc R 1 . H
  C6 0.8466(2) -0.0880(3) -0.1714(2) 0.0865(7) Uani d . 1 . C
  H6 0.8621(2) -0.1560(3) -0.2064(2) 0.104 Uiso calc R 1 . H
  C7 0.8133(2) 0.0400(3) -0.19625(13) 0.0822(7) Uani d . 1 . C
  H7 0.8064(2) 0.0608(3) -0.24743(13) 0.099 Uiso calc R 1 . H
  C8 0.7898(2) 0.1394(2) -0.14200(11) 0.0645(5) Uani d . 1 . C
  C9 0.8024(2) 0.1112(2) -0.06471(9) 0.0554(4) Uani d . 1 . C
  N1' 0.48177(15) 0.0621(2) 0.11606(10) 0.0714(5) Uani d . 1 . N
  H1' 0.39967(15) 0.0408(2) 0.11210(10) 0.086 Uiso calc R 1 . H
  C2' 0.5428(2) 0.1486(2) 0.06893(11) 0.0685(5) Uani d . 1 . C
  H2' 0.5018(2) 0.1913(2) 0.02684(11) 0.082 Uiso calc R 1 . H
  C3' 0.6719(2) 0.1631(2) 0.09231(9) 0.0529(4) Uani d . 1 . C
  C4' 0.8050(2) 0.0394(2) 0.20295(10) 0.0580(4) Uani d . 1 . C
  H4' 0.8870(2) 0.0761(2) 0.19476(10) 0.070 Uiso calc R 1 . H
  C5' 0.7914(2) -0.0522(2) 0.26037(12) 0.0707(5) Uani d . 1 . C
  H5' 0.8651(2) -0.0778(2) 0.29097(12) 0.085 Uiso calc R 1 . H
  C6' 0.6691(2) -0.1078(2) 0.27376(12) 0.0748(6) Uani d . 1 . C
  H6' 0.6628(2) -0.1685(2) 0.31369(12) 0.090 Uiso calc R 1 . H
  C7' 0.5590(2) -0.0754(2) 0.22978(12) 0.0697(5) Uani d . 1 . C
  H7' 0.4776(2) -0.1125(2) 0.23909(12) 0.084 Uiso calc R 1 . H
  C8' 0.5721(2) 0.0152(2) 0.17035(10) 0.0583(4) Uani d . 1 . C
  C9' 0.6936(2) 0.0768(2) 0.15673(9) 0.0502(4) Uani d . 1 . C
  C10 0.77449(15) 0.2516(2) 0.05836(9) 0.0513(4) Uani d . 1 . C
  H10 0.86040(15) 0.2179(2) 0.07871(9) 0.062 Uiso calc R 1 . H
  C11 0.7684(2) 0.4031(2) 0.07932(9) 0.0554(4) Uani d . 1 . C
  C12 0.8827(2) 0.4804(2) 0.08182(12) 0.0703(5) Uani d . 1 . C
  H12 0.9621(2) 0.4384(2) 0.07294(12) 0.084 Uiso calc R 1 . H
  C13 0.8803(3) 0.6197(2) 0.09741(15) 0.0872(7) Uani d . 1 . C
  H13 0.9578(3) 0.6702(2) 0.09869(15) 0.105 Uiso calc R 1 . H
  C14 0.7646(3) 0.6829(2) 0.11086(14) 0.0888(7) Uani d . 1 . C
  H14 0.7632(3) 0.7763(2) 0.12118(14) 0.107 Uiso calc R 1 . H
  C15 0.6509(3) 0.6080(2) 0.1091(2) 0.0917(7) Uani d . 1 . C
  H15 0.5720(3) 0.6506(2) 0.1184(2) 0.110 Uiso calc R 1 . H
  C16 0.6527(2) 0.4693(2) 0.09353(14) 0.0765(6) Uani d . 1 . C
  H16 0.5747(2) 0.4196(2) 0.09261(14) 0.092 Uiso calc R 1 . H
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
  N1 0.1117(14) 0.0711(10) 0.0530(8) -0.0212(9) 0.0041(8) 0.0070(7)
  C2 0.0873(12) 0.0531(9) 0.0623(10) -0.0098(9) 0.0057(9) 0.0035(8)
  C3 0.0535(8) 0.0493(8) 0.0562(9) -0.0092(6) 0.0054(6) -0.0007(7)
  C4 0.0510(9) 0.0561(10) 0.0897(13) -0.0027(7) -0.0035(8) -0.0059(9)
  C5 0.0557(10) 0.0654(12) 0.128(2) 0.0006(9) 0.0028(11) -0.0279(13)
  C6 0.0660(12) 0.083(2) 0.112(2) -0.0167(10) 0.0214(11) -0.0403(14)
  C7 0.0752(12) 0.102(2) 0.0720(12) -0.0322(12) 0.0196(10) -0.0270(11)
  C8 0.0672(10) 0.0664(11) 0.0611(10) -0.0220(8) 0.0122(8) -0.0072(8)
  C9 0.0480(8) 0.0555(9) 0.0628(10) -0.0117(7) 0.0052(7) -0.0073(7)
  N1' 0.0492(8) 0.0819(11) 0.0822(11) -0.0168(7) -0.0022(7) 0.0146(8)
  C2' 0.0583(10) 0.0765(12) 0.0692(11) -0.0136(9) -0.0056(8) 0.0134(9)
  C3' 0.0521(8) 0.0515(8) 0.0550(8) -0.0071(6) 0.0019(6) -0.0020(7)
  C4' 0.0568(9) 0.0477(8) 0.0687(10) 0.0012(7) -0.0012(7) -0.0049(7)
  C5' 0.0835(13) 0.0525(9) 0.0743(12) 0.0079(9) -0.0072(10) 0.0030(8)
  C6' 0.0979(15) 0.0534(10) 0.0743(12) 0.0052(10) 0.0135(10) 0.0130(9)
  C7' 0.0753(12) 0.0565(10) 0.0790(12) -0.0065(9) 0.0180(9) 0.0085(9)
  C8' 0.0562(9) 0.0537(9) 0.0657(10) -0.0060(7) 0.0086(7) -0.0004(7)
  C9' 0.0523(8) 0.0428(8) 0.0558(8) -0.0030(6) 0.0053(6) -0.0064(6)
  C10 0.0483(8) 0.0513(8) 0.0540(8) -0.0072(6) 0.0021(6) -0.0008(6)
  C11 0.0608(9) 0.0545(9) 0.0510(8) -0.0081(7) 0.0040(6) -0.0053(7)
  C12 0.0691(11) 0.0628(11) 0.0793(12) -0.0146(9) 0.0083(9) -0.0121(9)
  C13 0.095(2) 0.0688(13) 0.098(2) -0.0295(12) 0.0129(12) -0.0171(12)
  C14 0.118(2) 0.0573(12) 0.092(2) -0.0079(12) 0.0173(14) -0.0140(11)
  C15 0.093(2) 0.0689(13) 0.115(2) 0.0069(12) 0.0211(14) -0.0212(13)
  C16 0.0683(12) 0.0676(12) 0.0947(15) -0.0052(9) 0.0131(10) -0.0143(10)
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 C8 . 1.360(3) Yes
  N1 C2 . 1.369(3) Yes
  N1 H1 . 0.86 Yes
  C2 C3 . 1.349(2) ?
  C2 H2 . 0.93 ?
  C3 C9 . 1.434(2) ?
  C3 C10 . 1.502(2) ?
  C4 C5 . 1.380(3) ?
  C4 C9 . 1.407(3) ?
  C4 H4 . 0.93 ?
  C5 C6 . 1.389(4) ?
  C5 H5 . 0.93 ?
  C6 C7 . 1.360(4) ?
  C6 H6 . 0.93 ?
  C7 C8 . 1.401(3) ?
  C7 H7 . 0.93 ?
  C8 C9 . 1.399(3) ?
  N1' C2' . 1.369(2) Yes
  N1' C8' . 1.365(2) Yes
  N1' H1' . 0.86 Yes
  C2' C3' . 1.358(2) ?
  C2' H2' . 0.93 ?
  C3' C9' . 1.426(2) ?
  C3' C10 . 1.513(2) ?
  C4' C5' . 1.371(3) ?
  C4' C9' . 1.402(2) ?
  C4' H4' . 0.93 ?
  C5' C6' . 1.394(3) ?
  C5' H5' . 0.93 ?
  C6' C7' . 1.359(3) ?
  C6' H6' . 0.93 ?
  C7' C8' . 1.392(3) ?
  C7' H7' . 0.93 ?
  C8' C9' . 1.412(2) ?
  C10 C11 . 1.527(2) ?
  C10 H10 . 0.98 ?
  C11 C16 . 1.383(3) ?
  C11 C12 . 1.386(3) ?
  C12 C13 . 1.388(3) ?
  C12 H12 . 0.93 ?
  C13 C14 . 1.366(4) ?
  C13 H13 . 0.93 ?
  C14 C15 . 1.369(3) ?
  C14 H14 . 0.93 ?
  C15 C16 . 1.381(3) ?
  C15 H15 . 0.93 ?
  C16 H16 . 0.93 ?