#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008292.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_2008292
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  454
_journal_page_last  455
_publ_section_title
;
Crystallographic evidence of the formation of an
N-alkylated enammonium salt: 5-ethoxycarbonylmethyl-1-ethyl-
2,3,6,7-tetrahydro-4H,12H-indolo[2,3-a]quinolizin-5-ium
trifluoromethanesulfonate
;
loop_
_publ_author_name
  'Bombicz, Petra'
  'K\'alm\'an, Alajos'
_chemical_formula_moiety  'C21 H27 N2 O2^+^, C1 F3 S1 O3^-^'
_chemical_formula_sum  'C22 H27 F3 N2 O5 S1'
_chemical_formula_weight  488.52
_chemical_melting_point  176--178
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  14.910(2)
_cell_length_b  10.2990(10)
_cell_length_c  15.1840(10)
_cell_angle_alpha  90.000(10)
_cell_angle_beta  92.930(10)
_cell_angle_gamma  90.000(10)
_cell_volume  2328.6(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.393
_diffrn_ambient_temperature  293(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C1 0.96009(14) -0.4897(2) 0.30643(14) 0.0429(5) Uani d . 1 A1 C
  C2 1.01033(16) -0.4805(2) 0.22314(16) 0.0541(6) Uani d . 1 A1 C
  H2A 0.9721 -0.5135 0.1746 0.070(2) Uiso calc R 1 A1 H
  H2B 1.0628 -0.5362 0.2290 0.070(2) Uiso calc R 1 A1 H
  C3 1.04052(17) -0.3451(3) 0.20018(17) 0.0584(6) Uani d . 1 A1 C
  H3A 1.0904 -0.3496 0.1617 0.070(2) Uiso calc R 1 A1 H
  H3B 0.9917 -0.2985 0.1697 0.070(2) Uiso calc R 1 A1 H
  C4 1.06891(14) -0.2759(3) 0.28399(17) 0.0538(6) Uani d . 1 A1 C
  H4A 1.0921 -0.1908 0.2698 0.070(2) Uiso calc R 1 A1 H
  H4B 1.1169 -0.3243 0.3145 0.070(2) Uiso calc R 1 A1 H
  N5 0.99155(10) -0.26039(17) 0.34464(11) 0.0405(4) Uani d . 1 A1 N
  C6 1.03408(14) -0.2007(2) 0.42932(14) 0.0484(5) Uani d . 1 A1 C
  H6A 1.0788 -0.2600 0.4547 0.070(2) Uiso calc R 1 A1 H
  H6B 1.0644 -0.1208 0.4148 0.070(2) Uiso calc R 1 A1 H
  C7 0.96623(15) -0.1721(2) 0.49641(14) 0.0464(5) Uani d . 1 A1 C
  H7A 0.9966 -0.1507 0.5526 0.070(2) Uiso calc R 1 A1 H
  H7B 0.9296 -0.0985 0.4774 0.070(2) Uiso calc R 1 A1 H
  C7A 0.90852(13) -0.2887(2) 0.50627(13) 0.0410(4) Uani d . 1 A1 C
  C7B 0.85223(13) -0.3221(2) 0.57629(14) 0.0423(4) Uani d . 1 A1 C
  C8 0.83393(15) -0.2629(2) 0.65643(15) 0.0496(5) Uani d . 1 A1 C
  H8 0.8595 -0.1833 0.6722 0.068(4) Uiso calc R 1 A1 H
  C9 0.77704(17) -0.3256(3) 0.71135(17) 0.0576(6) Uani d . 1 A1 C
  H9 0.7646 -0.2880 0.7650 0.068(4) Uiso calc R 1 A1 H
  C10 0.73777(17) -0.4449(3) 0.68773(18) 0.0594(6) Uani d . 1 A1 C
  H10 0.6994 -0.4846 0.7260 0.068(4) Uiso calc R 1 A1 H
  C11 0.75457(16) -0.5050(2) 0.60906(17) 0.0541(6) Uani d . 1 A1 C
  H11 0.7280 -0.5840 0.5935 0.068(4) Uiso calc R 1 A1 H
  C11a 0.81297(14) -0.4428(2) 0.55381(15) 0.0446(5) Uani d . 1 A1 C
  N12 0.84354(12) -0.48078(17) 0.47405(12) 0.0455(4) Uani d . 1 A1 N
  H12 0.8287 -0.5511 0.4464 0.052(7) Uiso calc R 1 A1 H
  C12a 0.90239(13) -0.38689(19) 0.44523(13) 0.0395(4) Uani d . 1 A1 C
  C12b 0.95058(12) -0.3918(2) 0.36369(13) 0.0391(4) Uani d . 1 A1 C
  C14 0.92005(16) -0.6220(2) 0.31884(15) 0.0491(5) Uani d . 1 A1 C
  H14A 0.9138 -0.6376 0.3812 0.070(2) Uiso calc R 1 A1 H
  H14B 0.9603 -0.6874 0.2972 0.070(2) Uiso calc R 1 A1 H
  C13 0.82828(19) -0.6345(3) 0.27004(18) 0.0677(7) Uani d . 1 A1 C
  H13A 0.8078 -0.7227 0.2734 0.122(7) Uiso calc R 1 A1 H
  H13B 0.8332 -0.6106 0.2094 0.122(7) Uiso calc R 1 A1 H
  H13C 0.7862 -0.5782 0.2967 0.122(7) Uiso calc R 1 A1 H
  C15 0.91758(14) -0.1770(2) 0.30213(14) 0.0423(4) Uani d . 1 A1 C
  H15A 0.8866 -0.2264 0.2555 0.070(2) Uiso calc R 1 A1 H
  H15B 0.8744 -0.1570 0.3459 0.070(2) Uiso calc R 1 A1 H
  C16 0.95098(17) -0.0511(2) 0.26386(15) 0.0514(5) Uani d . 1 A1 C
  O21 0.90366(19) -0.02390(19) 0.19120(13) 0.0868(7) Uani d . 1 A1 O
  O22 1.01046(16) 0.01461(19) 0.29439(14) 0.0769(6) Uani d . 1 A1 O
  C17 0.9309(5) 0.0923(4) 0.1456(3) 0.147(2) Uani d D 1 A1 C
  H17A 0.8802 0.1510 0.1381 0.070(2) Uiso calc R 1 A1 H
  H17B 0.9779 0.1363 0.1806 0.070(2) Uiso calc R 1 A1 H
  C18A 0.9625(14) 0.0605(14) 0.0627(8) 0.201(8) Uani d PD 0.50 A1 C
  H18A 0.9817 0.1418 0.0390 0.122(7) Uiso d PR 0.50 A1 H
  H18B 0.9971 -0.0088 0.0393 0.122(7) Uiso d PR 0.50 A1 H
  H18C 0.9000 0.0472 0.0466 0.122(7) Uiso d PR 0.50 A1 H
  C18B 0.8801(7) 0.1204(8) 0.0678(5) 0.105(3) Uani d PD 0.50 B2 C
  H18D 0.9015 0.1986 0.0416 0.122(7) Uiso d PR 0.50 B2 H
  H18E 0.8846 0.0497 0.0270 0.122(7) Uiso d PR 0.50 B2 H
  H18F 0.8186 0.1315 0.0819 0.122(7) Uiso d PR 0.50 B2 H
  C19 0.6906(3) 0.0521(4) 0.5164(2) 0.0943(12) Uani d . 1 C1 C
  F26 0.7461(3) 0.0361(3) 0.58605(14) 0.1470(12) Uani d . 1 C1 F
  F27 0.6223(2) 0.1141(5) 0.5450(3) 0.1874(17) Uani d . 1 C1 F
  F28 0.6611(3) -0.0620(3) 0.49144(19) 0.1847(18) Uani d . 1 C1 F
  S20 0.74249(4) 0.13729(5) 0.42916(4) 0.04759(19) Uani d . 1 C1 S
  O23 0.67477(14) 0.1441(2) 0.36069(13) 0.0743(6) Uani d . 1 C1 O
  O24 0.76775(15) 0.25776(19) 0.46921(14) 0.0742(6) Uani d . 1 C1 O
  O25 0.81735(17) 0.0580(3) 0.41141(17) 0.0973(8) Uani d . 1 C1 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
  C1 0.0369(10) 0.0444(11) 0.0473(11) 0.0048(8) 0.0018(8) -0.0024(9)
  C2 0.0492(12) 0.0583(14) 0.0558(13) 0.0068(10) 0.0123(10) -0.0069(11)
  C3 0.0541(13) 0.0627(15) 0.0603(14) 0.0014(11) 0.0223(11) -0.0017(11)
  C4 0.0371(10) 0.0587(14) 0.0670(14) -0.0052(9) 0.0174(10) -0.0007(11)
  N5 0.0322(8) 0.0441(9) 0.0451(9) -0.0036(7) 0.0020(6) -0.0005(7)
  C6 0.0418(10) 0.0533(12) 0.0490(11) -0.0127(9) -0.0072(9) 0.0008(9)
  C7 0.0515(11) 0.0422(11) 0.0447(11) -0.0105(9) -0.0040(9) -0.0027(9)
  C7a 0.0410(10) 0.0372(10) 0.0446(10) -0.0022(8) -0.0002(8) -0.0010(8)
  C7b 0.0401(10) 0.0397(10) 0.0474(11) 0.0025(8) 0.0037(8) -0.0013(8)
  C8 0.0511(12) 0.0462(12) 0.0517(12) 0.0044(9) 0.0044(9) -0.0071(9)
  C9 0.0560(13) 0.0616(14) 0.0566(13) 0.0091(11) 0.0162(11) -0.0062(11)
  C10 0.0541(13) 0.0620(15) 0.0641(15) 0.0044(11) 0.0223(11) 0.0037(12)
  C11 0.0497(12) 0.0479(12) 0.0662(14) -0.0039(10) 0.0170(10) 0.0006(11)
  C11a 0.0415(10) 0.0406(11) 0.0524(11) -0.0001(8) 0.0089(9) -0.0020(9)
  N12 0.0472(9) 0.0371(9) 0.0532(10) -0.0075(7) 0.0121(8) -0.0067(7)
  C12a 0.0367(9) 0.0369(10) 0.0451(10) -0.0025(8) 0.0027(8) -0.0008(8)
  C12b 0.0322(9) 0.0400(10) 0.0450(10) -0.0005(7) 0.0017(7) -0.0002(8)
  C14 0.0584(13) 0.0397(11) 0.0489(11) 0.0045(9) 0.0016(10) -0.0061(9)
  C13 0.0672(16) 0.0725(18) 0.0622(15) -0.0205(14) -0.0083(13) 0.0042(13)
  C15 0.0410(10) 0.0421(10) 0.0437(10) -0.0010(8) -0.0001(8) -0.0004(8)
  C16 0.0683(14) 0.0417(11) 0.0445(11) -0.0005(10) 0.0049(10) -0.0041(9)
  O21 0.150(2) 0.0502(11) 0.0566(11) -0.0075(12) -0.0274(12) 0.0074(8)
  O22 0.0937(15) 0.0570(11) 0.0788(13) -0.0285(11) -0.0061(11) 0.0063(10)
  C17 0.311(8) 0.0501(18) 0.075(2) -0.019(3) -0.040(4) 0.0165(17)
  C18A 0.30(2) 0.144(12) 0.167(14) -0.022(13) 0.101(15) 0.036(10)
  C18B 0.162(8) 0.078(5) 0.071(4) -0.017(5) -0.026(5) 0.013(4)
  C19 0.128(3) 0.089(2) 0.0657(19) -0.037(2) 0.006(2) 0.0120(17)
  F26 0.234(3) 0.144(2) 0.0597(12) -0.032(2) -0.0240(16) 0.0338(13)
  F27 0.143(3) 0.255(5) 0.174(3) -0.013(3) 0.099(3) 0.032(3)
  F28 0.312(5) 0.125(2) 0.116(2) -0.140(3) -0.005(2) 0.0294(17)
  S20 0.0504(3) 0.0431(3) 0.0484(3) -0.0043(2) -0.0056(2) 0.0011(2)
  O23 0.0724(12) 0.0769(13) 0.0705(12) -0.0179(10) -0.0274(10) 0.0171(10)
  O24 0.0892(14) 0.0519(11) 0.0803(13) -0.0228(10) -0.0062(11) -0.0094(9)
  O25 0.0916(16) 0.1009(18) 0.0995(17) 0.0422(14) 0.0062(13) -0.0083(14)
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 C12b . 1.344(3) ?
  C1 C14 . 1.504(3) ?
  C1 C2 . 1.505(3) ?
  C2 C3 . 1.511(4) ?
  C3 C4 . 1.501(4) ?
  C4 N5 . 1.521(3) yes
  N5 C15 . 1.516(3) yes
  N5 C12b . 1.518(3) yes
  N5 C6 . 1.533(3) yes
  C6 C7 . 1.501(3) ?
  C7 C7a . 1.490(3) ?
  C7a C12a . 1.371(3) ?
  C7a C7b . 1.430(3) ?
  C7b C8 . 1.400(3) ?
  C7b C11a . 1.408(3) ?
  C8 C9 . 1.380(3) ?
  C9 C10 . 1.399(4) ?
  C10 C11 . 1.380(4) ?
  C11 C11a . 1.396(3) ?
  C11a N12 . 1.373(3) yes
  N12 C12a . 1.391(3) yes
  C12a C12b . 1.464(3) ?
  C14 C13 . 1.528(3) ?
  C15 C16 . 1.516(3) ?
  C16 O22 . 1.190(3) yes
  C16 O21 . 1.309(3) yes
  O21 C17 . 1.452(4) yes
  C17 C18A . 1.405(8) ?
  C17 C18B . 1.401(9) ?
  C19 F27 . 1.296(5) ?
  C19 F28 . 1.304(4) ?
  C19 F26 . 1.319(5) ?
  C19 S20 . 1.797(3) ?
  S20 O23 . 1.4135(18) ?
  S20 O25 . 1.420(2) ?
  S20 O24 . 1.4240(18) ?