#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012964.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_2012964
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o591
_journal_page_last  o592
_publ_section_title
;
(-)-(1'S,4aS,7R,8aR)-4a-Ethyl-1-(1'-phenylethyl)octahydroquinolinium-7-ol
bromide
;
loop_
_publ_author_name
  "V\'azquez, Edna"
  'Galindo, Alberto'
  "Bern\`es, Sylvain"
  'Gnecco, Dino'
_chemical_formula_moiety  'C19 H30 N O + , Br -'
_chemical_formula_sum  'C19 H30 Br N O'
_chemical_formula_weight  368.35
_chemical_melting_point  403
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  9.6977(8)
_cell_length_b  9.2191(7)
_cell_length_c  10.3008(8)
_cell_angle_alpha  90
_cell_angle_beta  92.624(7)
_cell_angle_gamma  90
_cell_volume  919.97(13)
_cell_formula_units_Z  2
_cell_measurement_temperature  300.0(10)
_exptl_crystal_density_diffrn  1.330
_diffrn_ambient_temperature  300.0(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
  Br1 0.41070(2) -0.06005(3) 0.71041(3) 0.05686(9) Uani d . 1 . . Br
  N1 0.2932(2) 0.2967(2) 0.67736(19) 0.0362(4) Uani d . 1 . . N
  H1 0.3168 0.2065 0.7068 0.043 Uiso d R 1 . . H
  C1' 0.1942(3) 0.2839(3) 0.5576(2) 0.0404(5) Uani d . 1 . . C
  H1'A 0.1799 0.3817 0.5221 0.048 Uiso calc R 1 . . H
  C2 0.4335(3) 0.3514(3) 0.6439(3) 0.0483(6) Uani d . 1 . . C
  H2A 0.4246 0.4477 0.6066 0.058 Uiso calc R 1 . . H
  H2B 0.4716 0.2881 0.5793 0.058 Uiso calc R 1 . . H
  C2' 0.2535(3) 0.1907(4) 0.4514(3) 0.0548(7) Uani d . 1 . . C
  H2'A 0.1888 0.1863 0.3781 0.082 Uiso calc R 1 . . H
  H2'B 0.2705 0.0945 0.4841 0.082 Uiso calc R 1 . . H
  H2'C 0.3385 0.2324 0.4251 0.082 Uiso calc R 1 . . H
  C3 0.5308(3) 0.3566(3) 0.7630(3) 0.0522(6) Uani d . 1 . . C
  H3A 0.6169 0.4011 0.7397 0.063 Uiso calc R 1 . . H
  H3B 0.5510 0.2583 0.7915 0.063 Uiso calc R 1 . . H
  C4 0.4722(2) 0.4412(4) 0.8752(2) 0.0459(5) Uani d . 1 . . C
  H4A 0.4667 0.5431 0.8521 0.055 Uiso calc R 1 . . H
  H4B 0.5344 0.4321 0.9512 0.055 Uiso calc R 1 . . H
  C4a 0.3282(2) 0.3873(3) 0.9088(2) 0.0377(5) Uani d . 1 . . C
  C5 0.2667(3) 0.4886(3) 1.0097(3) 0.0457(6) Uani d . 1 . . C
  H5A 0.1826 0.4449 1.0389 0.055 Uiso calc R 1 . . H
  H5B 0.3312 0.4950 1.0842 0.055 Uiso calc R 1 . . H
  C6 0.2334(3) 0.6418(3) 0.9622(3) 0.0527(7) Uani d . 1 . . C
  H6A 0.1903 0.6961 1.0302 0.063 Uiso calc R 1 . . H
  H6B 0.3179 0.6914 0.9415 0.063 Uiso calc R 1 . . H
  C7 0.1376(3) 0.6347(3) 0.8435(3) 0.0477(6) Uani d . 1 . . C
  H7A 0.0519 0.5881 0.8687 0.057 Uiso calc R 1 . . H
  C8 0.1976(3) 0.5428(3) 0.7367(3) 0.0434(6) Uani d . 1 . . C
  H8A 0.2808 0.5886 0.7076 0.052 Uiso calc R 1 . . H
  H8B 0.1316 0.5375 0.6632 0.052 Uiso calc R 1 . . H
  C8a 0.2319(2) 0.3891(2) 0.7848(2) 0.0331(5) Uani d . 1 . . C
  H8AA 0.1448 0.3435 0.8071 0.040 Uiso calc R 1 . . H
  C9 0.3428(3) 0.2344(3) 0.9701(3) 0.0460(6) Uani d . 1 . . C
  H9A 0.3858 0.1717 0.9080 0.055 Uiso calc R 1 . . H
  H9B 0.4058 0.2415 1.0457 0.055 Uiso calc R 1 . . H
  C10 0.2122(3) 0.1606(4) 1.0115(3) 0.0635(8) Uani d . 1 . . C
  H10A 0.2345 0.0663 1.0461 0.095 Uiso calc R 1 . . H
  H10B 0.1487 0.1507 0.9377 0.095 Uiso calc R 1 . . H
  H10C 0.1706 0.2180 1.0769 0.095 Uiso calc R 1 . . H
  C11 0.0548(3) 0.2270(3) 0.5962(2) 0.0381(5) Uani d . 1 . . C
  C12 -0.0640(3) 0.2955(3) 0.5487(3) 0.0481(6) Uani d . 1 . . C
  H12A -0.0571 0.3797 0.4996 0.058 Uiso calc R 1 . . H
  C12' 0.0431(3) 0.1028(3) 0.6703(2) 0.0405(5) Uani d . 1 . . C
  H12B 0.1222 0.0552 0.7022 0.049 Uiso calc R 1 . . H
  C13 -0.1929(3) 0.2402(4) 0.5732(3) 0.0532(7) Uani d . 1 . . C
  H13A -0.2720 0.2861 0.5394 0.064 Uiso calc R 1 . . H
  C13' -0.0859(3) 0.0487(3) 0.6974(3) 0.0459(6) Uani d . 1 . . C
  H13B -0.0929 -0.0336 0.7489 0.055 Uiso calc R 1 . . H
  C14 -0.2040(3) 0.1165(3) 0.6482(3) 0.0487(6) Uani d . 1 . . C
  H14A -0.2904 0.0793 0.6653 0.058 Uiso calc R 1 . . H
  O15 0.1029(2) 0.7752(2) 0.7937(2) 0.0677(6) Uani d . 1 . . O
  H15 0.1687 0.8096 0.7759 0.102 Uiso d 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
  Br1 0.05259(13) 0.04875(13) 0.06874(17) -0.00308(17) -0.00264(10)
  0.00670(17)
  N1 0.0352(9) 0.0334(9) 0.0404(10) -0.0005(8) 0.0055(8) -0.0021(8)
  C1' 0.0470(13) 0.0404(12) 0.0338(11) -0.0018(11) 0.0009(10) 0.0027(10)
  C2 0.0410(13) 0.0516(15) 0.0538(15) -0.0054(11) 0.0173(11) -0.0055(12)
  C2' 0.0604(18) 0.0638(18) 0.0409(14) -0.0062(15) 0.0103(13) -0.0106(13)
  C3 0.0350(12) 0.0540(15) 0.0682(17) -0.0020(12) 0.0072(12) -0.0117(14)
  C4 0.0394(10) 0.0423(10) 0.0556(12) -0.0057(17) -0.0005(9) -0.0038(18)
  C4a 0.0374(11) 0.0344(10) 0.0413(12) 0.0031(9) 0.0015(9) -0.0022(9)
  C5 0.0524(14) 0.0443(13) 0.0405(13) 0.0078(10) 0.0019(11) -0.0055(10)
  C6 0.0609(18) 0.0414(14) 0.0561(16) 0.0115(13) 0.0072(13) -0.0101(12)
  C7 0.0505(14) 0.0346(12) 0.0584(16) 0.0131(11) 0.0054(13) 0.0022(11)
  C8 0.0474(14) 0.0362(12) 0.0465(14) 0.0078(11) -0.0002(11) 0.0030(11)
  C8a 0.0337(11) 0.0306(10) 0.0355(11) 0.0022(8) 0.0063(9) -0.0006(8)
  C9 0.0520(15) 0.0411(13) 0.0448(14) 0.0070(11) -0.0004(11) 0.0054(11)
  C10 0.0680(19) 0.0523(16) 0.070(2) -0.0029(15) 0.0039(16) 0.0171(15)
  C11 0.0435(12) 0.0361(11) 0.0345(11) -0.0009(10) -0.0005(9) -0.0002(9)
  C12 0.0537(15) 0.0461(14) 0.0445(14) 0.0085(12) 0.0006(11) 0.0107(11)
  C12' 0.0426(12) 0.0360(11) 0.0426(13) 0.0027(10) -0.0017(10) 0.0003(10)
  C13 0.0452(15) 0.0674(19) 0.0468(15) 0.0132(13) -0.0003(12) 0.0020(14)
  C13' 0.0499(14) 0.0407(12) 0.0477(14) -0.0013(11) 0.0095(11) -0.0013(11)
  C14 0.0417(13) 0.0555(15) 0.0494(15) -0.0003(12) 0.0063(11) -0.0116(12)
  O15 0.0782(15) 0.0380(10) 0.0868(16) 0.0238(10) 0.0010(13) 0.0044(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 C2 . 1.506(3) n
  N1 C1' . 1.533(3) n
  N1 C8a . 1.538(3) y
  C1' C11 . 1.520(3) n
  C1' C2' . 1.524(4) n
  C2 C3 . 1.514(4) n
  C3 C4 . 1.525(4) n
  C4 C4a . 1.536(3) n
  C4a C5 . 1.538(3) y
  C4a C8a . 1.548(3) y
  C4a C9 . 1.548(3) y
  C5 C6 . 1.525(4) n
  C6 C7 . 1.503(4) n
  C7 O15 . 1.428(3) y
  C7 C8 . 1.525(4) n
  C8 C8a . 1.532(3) y
  C9 C10 . 1.516(4) n
  C11 C12 . 1.384(3) n
  C11 C12' . 1.384(3) n
  C12 C13 . 1.385(4) n
  C12' C13' . 1.386(4) n
  C13 C14 . 1.384(4) n
  C13' C14 . 1.381(4) n
  N1 H1 . 0.9103 ?
  C1' H1'A . 0.9800 ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C2' H2'A . 0.9600 ?
  C2' H2'B . 0.9600 ?
  C2' H2'C . 0.9600 ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 H7A . 0.9800 ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C8a H8AA . 0.9800 ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 H10A . 0.9600 ?
  C10 H10B . 0.9600 ?
  C10 H10C . 0.9600 ?
  C12 H12A . 0.9300 ?
  C12' H12B . 0.9300 ?
  C13 H13A . 0.9300 ?
  C13' H13B . 0.9300 ?
  C14 H14A . 0.9300 ?
  O15 H15 . 0.7429 ?