#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013745.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_2013745
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o118
_journal_page_last  o119
_publ_section_title
;
N-(2-Fluoroethyl)-3\b-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2\a-
carboxamide: a new cocaine derivative with equatorially attached ligands
;
loop_
_publ_author_name
  'Krebs, Birte'
  'Fl\"orke, Ulrich'
_chemical_formula_moiety  'C17 H22 F I N2 O'
_chemical_formula_sum  'C17 H22 F I N2 O'
_chemical_formula_iupac  'C17 H22 F I N2 O'
_chemical_formula_weight  416.27
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.9837(8)
_cell_length_b  9.5600(8)
_cell_length_c  10.1222(9)
_cell_angle_alpha  90
_cell_angle_beta  98.225(2)
_cell_angle_gamma  90
_cell_volume  860.39(13)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.607
_diffrn_ambient_temperature  120(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
  I1 1.08693(2) 0.24881(4) 1.17178(2) 0.03047(8) Uani d . 1 . . I
  O1 0.5589(3) 0.0690(3) 0.5609(3) 0.0261(6) Uani d . 1 . . O
  N2 0.5914(4) 0.2812(3) 0.4709(3) 0.0221(8) Uani d . 1 B . N
  H2B 0.5805 0.3702 0.4777 0.026 Uiso calc R 1 . . H
  N8 0.1984(4) 0.3609(4) 0.6762(4) 0.0233(8) Uani d . 1 . . N
  C1 0.2806(4) 0.2803(4) 0.5859(4) 0.0195(9) Uani d . 1 . . C
  H1A 0.2747 0.3275 0.4993 0.023 Uiso calc R 1 . . H
  C2 0.4464(4) 0.2699(4) 0.6530(3) 0.0168(9) Uani d . 1 . . C
  H2A 0.4860 0.3648 0.6691 0.020 Uiso calc R 1 . . H
  C3 0.4580(4) 0.1932(4) 0.7878(4) 0.0190(7) Uani d . 1 . . C
  H3A 0.4407 0.0934 0.7697 0.023 Uiso calc R 1 . . H
  C4 0.3341(3) 0.2461(9) 0.8679(3) 0.0248(7) Uani d . 1 . . C
  H4A 0.3272 0.1834 0.9420 0.030 Uiso calc R 1 . . H
  H4B 0.3612 0.3381 0.9040 0.030 Uiso calc R 1 . . H
  C5 0.1818(3) 0.2539(9) 0.7796(3) 0.0260(7) Uani d . 1 . . C
  H5A 0.1031 0.2814 0.8323 0.031 Uiso calc R 1 . . H
  C6 0.1376(5) 0.1186(5) 0.7015(5) 0.0280(10) Uani d . 1 . . C
  H6A 0.1815 0.0376 0.7499 0.034 Uiso calc R 1 . . H
  H6B 0.0292 0.1077 0.6855 0.034 Uiso calc R 1 . . H
  C7 0.2011(4) 0.1371(4) 0.5695(4) 0.0253(8) Uani d . 1 . . C
  H7A 0.1212 0.1375 0.4941 0.030 Uiso calc R 1 . . H
  H7B 0.2718 0.0631 0.5572 0.030 Uiso calc R 1 . . H
  C8 0.0528(5) 0.4082(5) 0.6092(5) 0.0345(10) Uani d . 1 . . C
  H8A -0.0099 0.3287 0.5833 0.052 Uiso calc R 1 . . H
  H8B 0.0667 0.4612 0.5313 0.052 Uiso calc R 1 . . H
  H8C 0.0057 0.4660 0.6688 0.052 Uiso calc R 1 . . H
  C9 0.6120(4) 0.2091(4) 0.8709(4) 0.0187(10) Uani d . 1 . . C
  C10 0.6691(5) 0.3383(5) 0.9113(4) 0.0247(10) Uani d . 1 . . C
  H10A 0.6150 0.4183 0.8826 0.030 Uiso calc R 1 . . H
  C11 0.8067(6) 0.3518(6) 0.9944(5) 0.0273(12) Uani d . 1 . . C
  H11A 0.8454 0.4399 1.0187 0.033 Uiso calc R 1 . . H
  C12 0.8839(4) 0.2335(7) 1.0396(3) 0.0232(9) Uani d . 1 . . C
  C13 0.8295(6) 0.1019(5) 0.9994(5) 0.0242(11) Uani d . 1 . . C
  H13A 0.8824 0.0217 1.0295 0.029 Uiso calc R 1 . . H
  C14 0.6946(5) 0.0920(5) 0.9134(4) 0.0245(10) Uani d . 1 . . C
  H14A 0.6593 0.0043 0.8839 0.029 Uiso calc R 1 . . H
  C15 0.5382(4) 0.1961(4) 0.5592(4) 0.0191(8) Uani d . 1 . . C
  C16 0.6671(4) 0.2258(5) 0.3644(3) 0.0232(11) Uani d . 1 . . C
  H16A 0.7174 0.1392 0.3941 0.028 Uiso calc R 1 A 1 H
  H16B 0.7431 0.2919 0.3453 0.028 Uiso calc R 1 A 1 H
  C17 0.5613(5) 0.1990(6) 0.2404(5) 0.0433(14) Uani d D 1 B 1 C
  H17A 0.6187 0.1622 0.1739 0.017(10) Uiso calc PR 0.50 B 1 H
  H17B 0.4918 0.1264 0.2592 0.017(10) Uiso calc PR 0.50 B 1 H
  H17C 0.6132 0.1398 0.1854 0.017(10) Uiso d PR 0.50 B 2 H
  H17D 0.5460 0.2871 0.1950 0.017(10) Uiso d PR 0.50 B 2 H
  F11 0.4840(7) 0.3034(5) 0.1889(5) 0.0555(19) Uani d PD 0.639(10) B 1 F
  F12 0.4368(8) 0.1468(10) 0.2443(8) 0.045(3) Uani d PD 0.361(10) B 2 F
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
  I1 0.02715(11) 0.03791(14) 0.02424(12) -0.00150(19) -0.00359(7) 0.00588(19)
  O1 0.0366(16) 0.0185(15) 0.0241(15) 0.0035(11) 0.0081(12) -0.0008(11)
  N2 0.0332(16) 0.011(2) 0.0230(16) -0.0010(12) 0.0068(13) 0.0003(11)
  N8 0.0223(19) 0.023(2) 0.024(2) 0.0050(14) 0.0007(15) -0.0023(14)
  C1 0.0236(16) 0.021(3) 0.0132(15) 0.0002(14) -0.0005(12) 0.0003(13)
  C2 0.0244(15) 0.009(3) 0.0163(15) 0.0021(14) -0.0001(11) -0.0001(14)
  C3 0.0227(17) 0.0184(18) 0.0149(17) 0.0022(13) -0.0007(14) 0.0009(14)
  C4 0.0281(15) 0.0320(19) 0.0140(14) -0.007(3) 0.0022(11) -0.005(3)
  C5 0.0250(15) 0.034(2) 0.0198(15) 0.004(3) 0.0046(12) 0.004(3)
  C6 0.027(2) 0.034(3) 0.023(2) -0.006(2) 0.0041(18) 0.0024(19)
  C7 0.031(2) 0.024(2) 0.019(2) -0.0010(17) -0.0008(16) -0.0021(16)
  C8 0.031(2) 0.040(3) 0.032(3) 0.012(2) -0.0003(19) 0.002(2)
  C9 0.0227(18) 0.022(3) 0.0106(17) 0.0036(14) 0.0010(14) -0.0001(13)
  C10 0.031(3) 0.021(3) 0.020(2) 0.007(2) -0.0031(18) 0.002(2)
  C11 0.038(3) 0.019(3) 0.023(2) -0.004(2) -0.002(2) -0.0061(19)
  C12 0.0217(14) 0.031(3) 0.0156(15) 0.005(2) 0.0002(11) 0.001(2)
  C13 0.025(2) 0.021(3) 0.024(2) 0.0044(19) -0.0019(17) 0.0037(19)
  C14 0.028(2) 0.022(3) 0.023(2) 0.0009(19) 0.0026(16) -0.0007(19)
  C15 0.0215(17) 0.0215(19) 0.0129(17) 0.0000(13) -0.0021(14) -0.0040(13)
  C16 0.0265(16) 0.022(3) 0.0221(17) 0.0023(16) 0.0081(13) 0.0018(16)
  C17 0.045(3) 0.065(4) 0.022(2) 0.006(2) 0.010(2) -0.011(2)
  F11 0.069(4) 0.067(4) 0.027(3) 0.035(3) -0.006(2) -0.001(2)
  F12 0.026(4) 0.067(7) 0.040(5) -0.006(4) -0.005(3) -0.021(4)
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
  I1 C12 . 2.107(3) y
  C15 O1 . 1.229(5) y
  N2 C15 . 1.346(5) y
  N2 C16 . 1.454(5) y
  N2 H2B . 0.8600 ?
  N8 C8 . 1.457(5) y
  N8 C1 . 1.472(5) y
  N8 C5 . 1.486(7) y
  C1 C7 . 1.542(5) ?
  C1 C2 . 1.549(5) ?
  C1 H1A . 0.9800 ?
  C2 C15 . 1.518(5) y
  C2 C3 . 1.539(5) y
  C2 H2A . 0.9800 ?
  C3 C9 . 1.520(5) y
  C3 C4 . 1.552(5) ?
  C3 H3A . 0.9800 ?
  C4 C5 . 1.525(4) ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.538(9) ?
  C5 H5A . 0.9800 ?
  C6 C7 . 1.536(6) ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8A . 0.9600 ?
  C8 H8B . 0.9600 ?
  C8 H8C . 0.9600 ?
  C9 C10 . 1.377(6) ?
  C9 C14 . 1.377(6) ?
  C10 C11 . 1.399(7) ?
  C10 H10A . 0.9300 ?
  C11 C12 . 1.371(8) ?
  C11 H11A . 0.9300 ?
  C12 C13 . 1.390(8) ?
  C13 C14 . 1.390(7) ?
  C13 H13A . 0.9300 ?
  C14 H14A . 0.9300 ?
  C16 C17 . 1.484(6) y
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 F11 . 1.284(6) y
  C17 F12 . 1.230(9) y
  C17 H17A . 0.9700 ?
  C17 H17B . 0.9700 ?
  C17 H17C . 0.9599 ?
  C17 H17D . 0.9600 ?