#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013775.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_2013775
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o6
_journal_page_last  o8
_publ_section_title
;
(Z)-2-(1H-Indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one
;
_space_group_IT_number           9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_[local]_cod_cif_authors_sg_H-M  'C c'
loop_
_publ_author_name
  'Sonar, Vijayakumar N.'
  'Parkin, Sean'
  'Crooks, Peter A.'
_chemical_formula_moiety  'C16 H16 N2 O'
_chemical_formula_sum  'C16 H16 N2 O'
_chemical_formula_weight  252.31
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y, z+1/2'
  'x+1/2, y+1/2, z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  6.1800(12)
_cell_length_b  44.160(9)
_cell_length_c  9.774(2)
_cell_angle_alpha  90.00
_cell_angle_beta  108.26(3)
_cell_angle_gamma  90.00
_cell_volume  2533.1(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  173.0(10)
_exptl_crystal_density_diffrn  1.323
_diffrn_ambient_temperature  173.0(10)
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
  N1A 1.0088(3) 0.47368(5) 0.2176(2) 0.0238(5) Uani d . 1 . . N
  H1A 1.0967 0.4780 0.1647 0.029 Uiso calc R 1 . . H
  C2A 0.8549(4) 0.49267(6) 0.2437(3) 0.0227(6) Uani d . 1 . . C
  H2A 0.8256 0.5127 0.2073 0.027 Uiso calc R 1 . . H
  C3A 0.7455(4) 0.47877(6) 0.3312(3) 0.0213(5) Uani d . 1 . . C
  C4A 0.8415(4) 0.44854(6) 0.3583(3) 0.0213(6) Uani d . 1 . . C
  C5A 0.8048(5) 0.42331(6) 0.4333(3) 0.0263(6) Uani d . 1 . . C
  H5A 0.6937 0.4240 0.4819 0.032 Uiso calc R 1 . . H
  C6A 0.9304(5) 0.39732(6) 0.4369(3) 0.0295(6) Uani d . 1 . . C
  H6A 0.9050 0.3801 0.4881 0.035 Uiso calc R 1 . . H
  C7A 1.0951(5) 0.39605(6) 0.3657(3) 0.0299(7) Uani d . 1 . . C
  H7A 1.1795 0.3779 0.3694 0.036 Uiso calc R 1 . . H
  C8A 1.1368(5) 0.42052(6) 0.2908(3) 0.0287(7) Uani d . 1 . . C
  H8A 1.2500 0.4197 0.2439 0.034 Uiso calc R 1 . . H
  C9A 1.0072(4) 0.44645(6) 0.2863(3) 0.0212(6) Uani d . 1 . . C
  C10A 0.5802(4) 0.49145(6) 0.3896(3) 0.0213(6) Uani d . 1 . . C
  H10A 0.5215 0.4780 0.4452 0.026 Uiso calc R 1 . . H
  C11A 0.4963(4) 0.51992(6) 0.3765(3) 0.0229(6) Uani d . 1 . . C
  N12A 0.5588(4) 0.54340(5) 0.2928(2) 0.0266(5) Uani d . 1 . . N
  C13A 0.3466(5) 0.55629(6) 0.1910(3) 0.0283(6) Uani d . 1 . . C
  H13A 0.2646 0.5403 0.1237 0.034 Uiso calc R 1 . . H
  H13B 0.3867 0.5726 0.1337 0.034 Uiso calc R 1 . . H
  C14A 0.1880(4) 0.56931(6) 0.2725(3) 0.0262(6) Uani d . 1 . . C
  H14A 0.1640 0.5912 0.2527 0.031 Uiso calc R 1 . . H
  H14B 0.0380 0.5591 0.2397 0.031 Uiso calc R 1 . . H
  C15A 0.3004(4) 0.56405(6) 0.4339(3) 0.0239(6) Uani d . 1 . . C
  H15A 0.2004 0.5714 0.4900 0.029 Uiso calc R 1 . . H
  C16A 0.5310(5) 0.58051(6) 0.4811(3) 0.0305(7) Uani d . 1 . . C
  H16A 0.6082 0.5773 0.5853 0.037 Uiso calc R 1 . . H
  H16B 0.5082 0.6025 0.4633 0.037 Uiso calc R 1 . . H
  C17A 0.6773(4) 0.56743(6) 0.3927(3) 0.0310(7) Uani d . 1 . . C
  H17A 0.7183 0.5840 0.3370 0.037 Uiso calc R 1 . . H
  H17B 0.8203 0.5591 0.4596 0.037 Uiso calc R 1 . . H
  C18A 0.3453(4) 0.53046(6) 0.4561(3) 0.0230(6) Uani d . 1 . . C
  O18A 0.2657(3) 0.51427(4) 0.5318(2) 0.0294(5) Uani d . 1 . . O
  N1B -0.1388(4) 0.77477(5) 0.5250(2) 0.0298(5) Uani d . 1 . . N
  H1B -0.2827 0.7717 0.4755 0.036 Uiso calc R 1 . . H
  C2B 0.0299(5) 0.75371(6) 0.5504(3) 0.0272(6) Uani d . 1 . . C
  H2B 0.0097 0.7334 0.5163 0.033 Uiso calc R 1 . . H
  C3B 0.2351(4) 0.76607(6) 0.6330(3) 0.0258(6) Uani d . 1 . . C
  C4B 0.1858(4) 0.79724(6) 0.6570(3) 0.0256(6) Uani d . 1 . . C
  C5B 0.3192(5) 0.82162(6) 0.7272(3) 0.0337(7) Uani d . 1 . . C
  H5B 0.4781 0.8192 0.7737 0.040 Uiso calc R 1 . . H
  C6B 0.2161(6) 0.84929(7) 0.7280(3) 0.0388(8) Uani d . 1 . . C
  H6B 0.3061 0.8661 0.7738 0.047 Uiso calc R 1 . . H
  C7B -0.0180(5) 0.85313(7) 0.6627(3) 0.0397(8) Uani d . 1 . . C
  H7B -0.0848 0.8723 0.6667 0.048 Uiso calc R 1 . . H
  C8B -0.1541(5) 0.82947(6) 0.5924(3) 0.0335(7) Uani d . 1 . . C
  H8B -0.3134 0.8320 0.5481 0.040 Uiso calc R 1 . . H
  C9B -0.0489(5) 0.80175(6) 0.5890(3) 0.0282(6) Uani d . 1 . . C
  C10B 0.4539(4) 0.75192(6) 0.6913(3) 0.0266(6) Uani d . 1 . . C
  H10B 0.5715 0.7646 0.7487 0.032 Uiso calc R 1 . . H
  C11B 0.5161(5) 0.72328(6) 0.6764(3) 0.0269(6) Uani d . 1 . . C
  N12B 0.3649(4) 0.70066(5) 0.5899(3) 0.0313(6) Uani d . 1 . . N
  C13B 0.3347(5) 0.67665(7) 0.6879(3) 0.0370(8) Uani d . 1 . . C
  H13C 0.2332 0.6607 0.6307 0.044 Uiso calc R 1 . . H
  H13D 0.2603 0.6854 0.7551 0.044 Uiso calc R 1 . . H
  C14B 0.5646(5) 0.66224(7) 0.7755(3) 0.0364(7) Uani d . 1 . . C
  H14C 0.5893 0.6648 0.8799 0.044 Uiso calc R 1 . . H
  H14D 0.5634 0.6403 0.7544 0.044 Uiso calc R 1 . . H
  C15B 0.7570(5) 0.67793(6) 0.7334(3) 0.0307(7) Uani d . 1 . . C
  H15B 0.9093 0.6696 0.7900 0.037 Uiso calc R 1 . . H
  C16B 0.7123(5) 0.67355(7) 0.5715(3) 0.0346(7) Uani d . 1 . . C
  H16C 0.7144 0.6517 0.5490 0.042 Uiso calc R 1 . . H
  H16D 0.8323 0.6838 0.5412 0.042 Uiso calc R 1 . . H
  C17B 0.4751(5) 0.68730(7) 0.4899(3) 0.0384(8) Uani d . 1 . . C
  H17C 0.4936 0.7031 0.4227 0.046 Uiso calc R 1 . . H
  H17D 0.3757 0.6713 0.4322 0.046 Uiso calc R 1 . . H
  C18B 0.7440(5) 0.71166(6) 0.7582(3) 0.0282(6) Uani d . 1 . . C
  O18B 0.9001(3) 0.72689(5) 0.8357(2) 0.0362(5) Uani d . 1 . . O
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
  N1A 0.0216(11) 0.0285(12) 0.0246(12) -0.0013(10) 0.0120(10) 0.0009(10)
  C2A 0.0223(14) 0.0235(13) 0.0231(15) 0.0000(12) 0.0080(12) 0.0003(12)
  C3A 0.0168(12) 0.0236(13) 0.0221(14) -0.0003(11) 0.0042(10) 0.0002(12)
  C4A 0.0173(13) 0.0262(14) 0.0178(14) -0.0022(11) 0.0020(11) -0.0023(11)
  C5A 0.0237(14) 0.0302(15) 0.0234(15) -0.0036(12) 0.0051(12) -0.0013(12)
  C6A 0.0352(16) 0.0230(14) 0.0271(16) -0.0019(12) 0.0050(13) 0.0030(12)
  C7A 0.0334(16) 0.0234(14) 0.0300(16) 0.0083(12) 0.0057(13) -0.0012(12)
  C8A 0.0249(15) 0.0332(16) 0.0277(16) 0.0034(12) 0.0076(12) -0.0039(13)
  C9A 0.0167(13) 0.0249(14) 0.0203(14) -0.0033(11) 0.0032(11) -0.0037(12)
  C10A 0.0183(13) 0.0275(14) 0.0180(14) -0.0029(11) 0.0055(11) 0.0039(11)
  C11A 0.0185(13) 0.0272(14) 0.0247(14) -0.0003(11) 0.0093(11) 0.0026(12)
  N12A 0.0270(12) 0.0263(12) 0.0303(13) 0.0055(10) 0.0144(10) 0.0077(11)
  C13A 0.0339(16) 0.0277(14) 0.0257(16) 0.0061(12) 0.0129(13) 0.0053(12)
  C14A 0.0240(14) 0.0252(14) 0.0292(15) 0.0029(11) 0.0081(12) 0.0047(12)
  C15A 0.0190(13) 0.0312(14) 0.0234(15) 0.0022(11) 0.0093(11) -0.0002(12)
  C16A 0.0256(14) 0.0305(15) 0.0332(17) -0.0012(12) 0.0062(13) -0.0020(13)
  C17A 0.0215(14) 0.0296(15) 0.0433(18) 0.0002(12) 0.0123(13) 0.0082(14)
  C18A 0.0169(14) 0.0298(15) 0.0208(14) -0.0003(11) 0.0037(11) 0.0013(12)
  O18A 0.0273(11) 0.0350(11) 0.0315(12) 0.0022(8) 0.0174(9) 0.0044(9)
  N1B 0.0188(12) 0.0366(13) 0.0321(14) 0.0001(10) 0.0051(10) 0.0034(11)
  C2B 0.0238(14) 0.0280(15) 0.0273(16) 0.0035(12) 0.0046(12) 0.0051(12)
  C3B 0.0231(14) 0.0307(15) 0.0242(15) 0.0024(12) 0.0084(12) 0.0046(12)
  C4B 0.0218(14) 0.0336(16) 0.0225(14) 0.0007(11) 0.0085(11) 0.0027(12)
  C5B 0.0293(16) 0.0405(17) 0.0294(16) 0.0020(14) 0.0065(13) 0.0008(14)
  C6B 0.048(2) 0.0311(16) 0.0385(19) -0.0018(15) 0.0148(16) -0.0031(14)
  C7B 0.050(2) 0.0367(17) 0.0343(18) 0.0146(15) 0.0168(16) 0.0059(15)
  C8B 0.0318(16) 0.0392(17) 0.0311(17) 0.0118(14) 0.0121(14) 0.0081(14)
  C9B 0.0262(15) 0.0358(17) 0.0242(15) 0.0025(13) 0.0103(12) 0.0054(13)
  C10B 0.0201(14) 0.0367(16) 0.0238(15) 0.0005(12) 0.0081(11) 0.0034(13)
  C11B 0.0200(14) 0.0354(16) 0.0250(15) 0.0042(12) 0.0063(11) 0.0016(13)
  N12B 0.0223(12) 0.0349(14) 0.0331(14) 0.0041(10) 0.0034(11) -0.0063(12)
  C13B 0.0262(15) 0.0354(16) 0.050(2) -0.0022(13) 0.0125(14) -0.0036(15)
  C14B 0.0287(16) 0.0427(18) 0.0403(19) 0.0037(14) 0.0145(14) 0.0035(15)
  C15B 0.0216(15) 0.0386(16) 0.0335(17) 0.0078(12) 0.0108(13) 0.0026(13)
  C16B 0.0277(16) 0.0418(18) 0.0347(17) 0.0047(13) 0.0101(13) -0.0044(14)
  C17B 0.0323(17) 0.0456(18) 0.0331(18) 0.0064(14) 0.0041(14) -0.0096(15)
  C18B 0.0222(14) 0.0410(17) 0.0230(15) 0.0004(13) 0.0093(12) -0.0011(14)
  O18B 0.0201(10) 0.0481(12) 0.0356(12) 0.0014(9) 0.0020(9) -0.0053(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
  N1A C2A . 1.351(3) ?
  N1A C9A . 1.379(3) ?
  N1A H1A . 0.8800 ?
  C2A C3A . 1.388(4) y
  C2A H2A . 0.9500 ?
  C3A C10A . 1.431(4) y
  C3A C4A . 1.451(3) ?
  C4A C5A . 1.391(4) ?
  C4A C9A . 1.415(3) ?
  C5A C6A . 1.380(4) ?
  C5A H5A . 0.9500 ?
  C6A C7A . 1.402(4) ?
  C6A H6A . 0.9500 ?
  C7A C8A . 1.374(4) ?
  C7A H7A . 0.9500 ?
  C8A C9A . 1.390(4) ?
  C8A H8A . 0.9500 ?
  C10A C11A . 1.351(3) y
  C10A H10A . 0.9500 ?
  C11A N12A . 1.446(3) ?
  C11A C18A . 1.466(4) y
  N12A C17A . 1.472(4) ?
  N12A C13A . 1.489(3) ?
  C13A C14A . 1.554(4) ?
  C13A H13A . 0.9900 ?
  C13A H13B . 0.9900 ?
  C14A C15A . 1.529(4) ?
  C14A H14A . 0.9900 ?
  C14A H14B . 0.9900 ?
  C15A C18A . 1.512(3) ?
  C15A C16A . 1.536(4) ?
  C15A H15A . 1.0000 ?
  C16A C17A . 1.545(4) ?
  C16A H16A . 0.9900 ?
  C16A H16B . 0.9900 ?
  C17A H17A . 0.9900 ?
  C17A H17B . 0.9900 ?
  C18A O18A . 1.236(3) y
  N1B C2B . 1.360(3) ?
  N1B C9B . 1.379(3) ?
  N1B H1B . 0.8800 ?
  C2B C3B . 1.384(4) y
  C2B H2B . 0.9500 ?
  C3B C10B . 1.436(4) y
  C3B C4B . 1.444(4) ?
  C4B C5B . 1.399(4) ?
  C4B C9B . 1.408(4) ?
  C5B C6B . 1.379(4) ?
  C5B H5B . 0.9500 ?
  C6B C7B . 1.397(5) ?
  C6B H6B . 0.9500 ?
  C7B C8B . 1.382(4) ?
  C7B H7B . 0.9500 ?
  C8B C9B . 1.391(4) ?
  C8B H8B . 0.9500 ?
  C10B C11B . 1.343(4) y
  C10B H10B . 0.9500 ?
  C11B N12B . 1.446(4) ?
  C11B C18B . 1.477(4) y
  N12B C17B . 1.478(4) ?
  N12B C13B . 1.479(4) ?
  C13B C14B . 1.548(4) ?
  C13B H13C . 0.9900 ?
  C13B H13D . 0.9900 ?
  C14B C15B . 1.539(4) ?
  C14B H14C . 0.9900 ?
  C14B H14D . 0.9900 ?
  C15B C18B . 1.515(4) ?
  C15B C16B . 1.531(4) ?
  C15B H15B . 1.0000 ?
  C16B C17B . 1.556(4) ?
  C16B H16C . 0.9900 ?
  C16B H16D . 0.9900 ?
  C17B H17C . 0.9900 ?
  C17B H17D . 0.9900 ?
  C18B O18B . 1.224(3) y
_cod_database_code 2013775