#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2013774
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o219
_journal_page_last  o222
_publ_section_title
;
An analysis of C-H...O and C-H...\p interactions in three substituted
4-ketotetrahydroindoles
;
loop_
_publ_author_name
  'Choudhury, A. R'
  'Nagarajan, K.'
  'Guru Row, T. N.'
_chemical_formula_moiety  'C22 H21 N O'
_chemical_formula_sum  'C22 H21 N O'
_chemical_formula_iupac  'C22 H21 N O'
_chemical_formula_weight  315.40
_chemical_melting_point  482
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,-y,-z
_cell_length_a  9.315(5)
_cell_length_b  9.793(5)
_cell_length_c  11.048(6)
_cell_angle_alpha  81.362(9)
_cell_angle_beta  65.691(7)
_cell_angle_gamma  77.999(8)
_cell_volume  896.0(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.169
_diffrn_ambient_temperature  273(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 0.28072(13) 0.23798(11) 0.69871(10) 0.0393(3) Uani d . 1 . . N
  O1 0.49380(13) 0.19296(13) 0.25063(10) 0.0642(3) Uani d . 1 . . O
  C1 0.15640(15) 0.26748(14) 0.65309(13) 0.0394(3) Uani d . 1 . . C
  C2 0.22397(16) 0.25684(15) 0.51884(13) 0.0420(3) Uani d . 1 . . C
  C3 0.51835(16) 0.19015(15) 0.35162(13) 0.0431(3) Uani d . 1 . . C
  C4 0.68424(17) 0.14790(18) 0.35118(15) 0.0487(4) Uani d . 1 . . C
  C5 0.71311(16) 0.21092(15) 0.45697(14) 0.0457(3) Uani d . 1 . . C
  C6 0.58507(17) 0.17938(17) 0.59576(15) 0.0455(3) Uani d . 1 . . C
  C7 0.42332(15) 0.21093(14) 0.59246(13) 0.0384(3) Uani d . 1 . . C
  C8 0.39170(15) 0.22049(14) 0.48016(13) 0.0394(3) Uani d . 1 . . C
  C9 0.26477(16) 0.24451(14) 0.83309(12) 0.0403(3) Uani d . 1 . . C
  C10 0.20043(18) 0.36894(16) 0.89371(15) 0.0489(4) Uani d . 1 . . C
  C11 0.1867(2) 0.37528(19) 1.02188(16) 0.0562(4) Uani d . 1 . . C
  C12 0.2375(2) 0.2583(2) 1.08890(16) 0.0605(5) Uani d . 1 . . C
  C13 0.3022(2) 0.1343(2) 1.02774(16) 0.0649(5) Uani d . 1 . . C
  C14 0.3162(2) 0.12617(17) 0.89933(15) 0.0547(4) Uani d . 1 . . C
  C15 -0.01448(16) 0.29904(15) 0.73970(13) 0.0424(3) Uani d . 1 . . C
  C16 -0.11164(17) 0.40663(17) 0.69814(15) 0.0508(4) Uani d . 1 . . C
  C17 -0.27475(19) 0.4344(2) 0.77108(19) 0.0637(5) Uani d . 1 . . C
  C18 -0.3431(2) 0.3564(2) 0.8878(2) 0.0696(5) Uani d . 1 . . C
  C19 -0.2492(2) 0.2513(2) 0.93185(19) 0.0705(5) Uani d . 1 . . C
  C20 -0.0853(2) 0.22134(18) 0.85879(16) 0.0584(4) Uani d . 1 . . C
  C21 0.8764(2) 0.1419(2) 0.4570(2) 0.0680(5) Uani d . 1 . . C
  C22 0.7097(3) 0.36887(19) 0.4255(2) 0.0652(5) Uani d . 1 . . C
  H2 0.1666(17) 0.2680(14) 0.4612(14) 0.045(4) Uiso d . 1 . . H
  H4A 0.761(2) 0.1727(17) 0.2616(18) 0.066(5) Uiso d . 1 . . H
  H4B 0.701(2) 0.0449(19) 0.3678(16) 0.067(5) Uiso d . 1 . . H
  H6A 0.6068(17) 0.0805(17) 0.6255(14) 0.050(4) Uiso d . 1 . . H
  H6B 0.5899(18) 0.2307(16) 0.6634(16) 0.054(4) Uiso d . 1 . . H
  H10 0.165(2) 0.4500(18) 0.8462(16) 0.065(5) Uiso d . 1 . . H
  H11 0.143(2) 0.463(2) 1.0643(17) 0.072(5) Uiso d . 1 . . H
  H12 0.230(2) 0.2643(18) 1.1758(18) 0.072(5) Uiso d . 1 . . H
  H13 0.337(2) 0.050(2) 1.0744(19) 0.086(6) Uiso d . 1 . . H
  H14 0.361(2) 0.039(2) 0.8553(18) 0.071(5) Uiso d . 1 . . H
  H16 -0.061(2) 0.4652(18) 0.6129(17) 0.067(5) Uiso d . 1 . . H
  H17 -0.342(2) 0.513(2) 0.7411(19) 0.085(6) Uiso d . 1 . . H
  H18 -0.457(3) 0.377(2) 0.938(2) 0.093(6) Uiso d . 1 . . H
  H19 -0.288(2) 0.198(2) 1.012(2) 0.090(6) Uiso d . 1 . . H
  H20 -0.018(2) 0.1455(18) 0.8871(16) 0.060(5) Uiso d . 1 . . H
  H21A 0.723(2) 0.416(2) 0.494(2) 0.091(7) Uiso d . 1 . . H
  H21B 0.609(2) 0.417(2) 0.4139(17) 0.075(5) Uiso d . 1 . . H
  H21C 0.800(3) 0.386(2) 0.337(2) 0.095(7) Uiso d . 1 . . H
  H22A 0.960(3) 0.158(2) 0.369(2) 0.099(7) Uiso d . 1 . . H
  H22B 0.880(2) 0.034(2) 0.478(2) 0.092(6) Uiso d . 1 . . H
  H22C 0.896(2) 0.178(2) 0.528(2) 0.089(6) Uiso d . 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 0.0375(6) 0.0475(7) 0.0306(6) -0.0048(5) -0.0117(5) -0.0048(5)
  O1 0.0511(6) 0.1027(9) 0.0342(6) -0.0018(6) -0.0143(5) -0.0137(5)
  C1 0.0350(7) 0.0462(8) 0.0361(7) -0.0062(6) -0.0129(6) -0.0038(6)
  C2 0.0366(7) 0.0553(9) 0.0346(7) -0.0062(6) -0.0149(6) -0.0040(6)
  C3 0.0418(8) 0.0486(8) 0.0354(8) -0.0058(6) -0.0119(6) -0.0049(6)
  C4 0.0379(8) 0.0564(10) 0.0429(9) -0.0015(7) -0.0083(7) -0.0086(7)
  C5 0.0350(7) 0.0514(8) 0.0482(8) -0.0049(6) -0.0145(6) -0.0048(6)
  C6 0.0424(8) 0.0537(9) 0.0432(8) -0.0059(6) -0.0208(7) -0.0029(7)
  C7 0.0365(7) 0.0424(7) 0.0347(7) -0.0059(5) -0.0125(6) -0.0032(5)
  C8 0.0362(7) 0.0471(8) 0.0325(7) -0.0059(6) -0.0112(6) -0.0040(5)
  C9 0.0398(7) 0.0484(8) 0.0317(7) -0.0076(6) -0.0124(6) -0.0041(6)
  C10 0.0519(9) 0.0498(9) 0.0447(8) -0.0034(7) -0.0198(7) -0.0065(7)
  C11 0.0569(10) 0.0655(11) 0.0468(9) -0.0026(8) -0.0187(8) -0.0215(8)
  C12 0.0609(10) 0.0862(13) 0.0355(8) -0.0107(9) -0.0186(8) -0.0107(8)
  C13 0.0783(12) 0.0709(12) 0.0437(9) -0.0018(9) -0.0295(9) 0.0032(8)
  C14 0.0690(10) 0.0510(9) 0.0409(8) -0.0006(8) -0.0222(8) -0.0052(7)
  C15 0.0378(7) 0.0510(8) 0.0368(7) -0.0095(6) -0.0099(6) -0.0100(6)
  C16 0.0421(8) 0.0638(10) 0.0440(9) -0.0036(7) -0.0145(7) -0.0104(7)
  C17 0.0430(9) 0.0809(12) 0.0659(11) 0.0009(8) -0.0189(8) -0.0243(9)
  C18 0.0384(9) 0.0863(13) 0.0745(13) -0.0114(9) -0.0033(9) -0.0321(10)
  C19 0.0604(11) 0.0804(13) 0.0532(11) -0.0303(10) 0.0051(9) -0.0086(9)
  C20 0.0526(9) 0.0614(10) 0.0500(9) -0.0139(8) -0.0083(8) 0.0005(8)
  C21 0.0403(9) 0.0882(15) 0.0744(13) -0.0021(9) -0.0237(9) -0.0108(11)
  C22 0.0676(12) 0.0571(10) 0.0710(13) -0.0197(9) -0.0248(10) 0.0015(9)
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 C7 . 1.3696(17) ?
  N1 C1 . 1.4057(18) ?
  N1 C9 . 1.4399(18) ?
  O1 C3 . 1.2231(17) ?
  C1 C2 . 1.363(2) ?
  C1 C15 . 1.4747(19) ?
  C2 C8 . 1.419(2) ?
  C2 H2 . 0.968(15) ?
  C3 C8 . 1.4486(19) ?
  C3 C4 . 1.512(2) ?
  C4 C5 . 1.537(2) ?
  C4 H4A . 0.984(17) ?
  C4 H4B . 0.989(18) ?
  C5 C22 . 1.530(2) ?
  C5 C21 . 1.530(2) ?
  C5 C6 . 1.541(2) ?
  C6 C7 . 1.488(2) ?
  C6 H6A . 0.982(16) ?
  C6 H6B . 0.982(17) ?
  C7 C8 . 1.3745(19) ?
  C9 C10 . 1.380(2) ?
  C9 C14 . 1.383(2) ?
  C10 C11 . 1.378(2) ?
  C10 H10 . 0.963(16) ?
  C11 C12 . 1.376(2) ?
  C11 H11 . 0.974(19) ?
  C12 C13 . 1.379(3) ?
  C12 H12 . 0.945(18) ?
  C13 C14 . 1.383(2) ?
  C13 H13 . 0.97(2) ?
  C14 H14 . 0.976(19) ?
  C15 C20 . 1.392(2) ?
  C15 C16 . 1.393(2) ?
  C16 C17 . 1.385(2) ?
  C16 H16 . 1.011(18) ?
  C17 C18 . 1.372(3) ?
  C17 H17 . 1.00(2) ?
  C18 C19 . 1.374(3) ?
  C18 H18 . 0.97(2) ?
  C19 C20 . 1.392(3) ?
  C19 H19 . 0.93(2) ?
  C20 H20 . 0.970(17) ?
  C21 H22A . 0.98(2) ?
  C21 H22B . 1.05(2) ?
  C21 H22C . 1.00(2) ?
  C22 H21A . 1.01(2) ?
  C22 H21B . 1.01(2) ?
  C22 H21C . 1.01(2) ?