#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/84/2008466.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_2008466
loop_
_publ_author_name
'Hartmann, Susanne'
'Weckert, Edgar'
'Frahm, August W.'
_publ_section_title
;
(1'R,2'R)-3-[(cis-2'-Cyclohexylmethylcyclopentyl)imino]-2-
azabicyclo[2.2.2]octane-hydrobromide, a hypoglycaemic semicyclic amidine
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              806
_journal_page_last               808
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C19 H33 N2 +, Br -'
_chemical_formula_sum            'C19 H33 Br N2'
_chemical_formula_weight         369.39
_chemical_melting_point          .506E-305
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.245(2)
_cell_length_b                   11.752(2)
_cell_length_c                   14.476(5)
_cell_measurement_temperature    150.0(10)
_cell_volume                     1913.0(8)
_diffrn_ambient_temperature      150(2)
_exptl_crystal_density_diffrn    1.282
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2008466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
H1 .504(2) .684(2) .3544(17) .035(6) Uiso d . 1 . . H
H2 .6191(19) .8632(19) .2083(14) .020(5) Uiso d . 1 . . H
Br .321938(14) .562498(14) .341986(11) .02681(6) Uani d . 1 . . Br1
N1 .55739(13) .72172(13) .37247(9) .0218(3) Uani d . 1 . . N
N2 .59422(13) .80942(13) .23019(10) .0212(3) Uani d . 1 . . N
C5 .78446(14) .80524(15) .42172(11) .0209(3) Uani d . 1 . . C
H51 .8334 .8542 .4623 .023 Uiso calc R 1 . . H
H52 .8375 .7698 .3753 .023 Uiso calc R 1 . . H
C3 .60889(14) .79902(14) .32023(11) .0194(3) Uani d . 1 . . C
C6 .72311(15) .71167(15) .47987(11) .0221(3) Uani d . 1 . . C
H61 .7464 .6355 .4569 .024 Uiso calc R 1 . . H
H62 .7478 .7180 .5453 .024 Uiso calc R 1 . . H
C1 .58823(15) .72703(15) .47177(11) .0220(3) Uani d . 1 . . C
H11 .5457 .6660 .5068 .024 Uiso calc R 1 . . H
C8 .61193(14) .93662(17) .44684(12) .0255(3) Uani d . 1 . . C
H81 .5498 .9835 .4168 .028 Uiso calc R 1 . . H
H82 .6621 .9872 .4852 .028 Uiso calc R 1 . . H
C5'' .09220(16) 1.09093(14) .27525(14) .0283(4) Uani d . 1 . . C
H5''1 .0843 1.1509 .3229 .031 Uiso calc R 1 . . H
H5''2 .0875 1.1279 .2139 .031 Uiso calc R 1 . . H
C4 .68901(15) .87784(14) .37258(11) .0201(3) Uani d . 1 . . C
H41 .7264 .9350 .3305 .022 Uiso calc R 1 . . H
C2' .39149(14) .79940(14) .15456(12) .0233(3) Uani d . 1 . . C
H2'1 .3302 .7381 .1490 .026 Uiso calc R 1 . . H
C1'' .22926(14) .93478(15) .21701(11) .0212(3) Uani d . 1 . . C
H1''1 .2266 .9673 .1532 .023 Uiso calc R 1 . . H
C4'' -.00968(16) 1.00661(16) .28517(14) .0303(4) Uani d . 1 . . C
H4''1 -.0862 1.0459 .2741 .033 Uiso calc R 1 . . H
H4''2 -.0107 .9757 .3488 .033 Uiso calc R 1 . . H
C1' .51443(15) .74107(14) .17237(11) .0215(3) Uani d . 1 . . C
H1'1 .5017 .6649 .2016 .024 Uiso calc R 1 . . H
C7'' .35180(15) .88056(15) .23073(12) .0232(4) Uani d . 1 . . C
H7''1 .4115 .9422 .2361 .026 Uiso calc R 1 . . H
H7''2 .3514 .8385 .2900 .026 Uiso calc R 1 . . H
C7 .55316(15) .84460(16) .50826(12) .0263(4) Uani d . 1 . . C
H71 .5801 .8533 .5730 .029 Uiso calc R 1 . . H
H72 .4656 .8532 .5068 .029 Uiso calc R 1 . . H
C3'' .00471(16) .90961(16) .21629(16) .0320(4) Uani d . 1 . . C
H3''1 -.0034 .9398 .1528 .035 Uiso calc R 1 . . H
H3''2 -.0594 .8531 .2262 .035 Uiso calc R 1 . . H
C2'' .12622(16) .85051(15) .22618(14) .0272(4) Uani d . 1 . . C
H2''1 .1306 .8128 .2872 .030 Uiso calc R 1 . . H
H2''2 .1339 .7911 .1781 .030 Uiso calc R 1 . . H
C5' .57150(16) .72548(17) .07564(12) .0284(4) Uani d . 1 . . C
H5'1 .6449 .7716 .0703 .031 Uiso calc R 1 . . H
H5'2 .5918 .6446 .0649 .031 Uiso calc R 1 . . H
C6'' .21267(15) 1.03299(15) .28548(13) .0267(4) Uani d . 1 . . C
H6''1 .2206 1.0034 .3492 .029 Uiso calc R 1 . . H
H6''2 .2763 1.0899 .2756 .029 Uiso calc R 1 . . H
C3' .4067(2) .8544(2) .05898(13) .0372(5) Uani d . 1 . . C
H3'1 .3287 .8680 .0292 .041 Uiso calc R 1 . . H
H3'2 .4503 .9274 .0634 .041 Uiso calc R 1 . . H
C4' .4787(2) .7655(2) .00600(14) .0448(6) Uani d . 1 . . C
H4'1 .4275 .7015 -.0140 .049 Uiso calc R 1 . . H
H4'2 .5171 .7995 -.0490 .049 Uiso calc 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
Br .02329(8) .02824(9) .02888(9) -.00318(7) .00292(7) -.01086(7)
N1 .0201(7) .0266(7) .0187(7) -.0058(6) -.0046(5) .0011(6)
N2 .0205(6) .0225(7) .0205(7) -.0004(6) -.0018(5) .0043(6)
C5 .0156(7) .0277(8) .0194(7) .0019(6) -.0002(6) -.0007(7)
C3 .0160(7) .0220(8) .0202(8) .0029(6) -.0013(6) .0018(6)
C6 .0231(8) .0250(8) .0181(7) .0017(7) -.0022(6) .0011(6)
C1 .0211(8) .0285(9) .0162(8) -.0024(7) -.0002(6) .0021(6)
C8 .0215(8) .0249(8) .0300(8) .0028(8) -.0006(6) -.0043(8)
C5'' .0301(9) .0204(8) .0344(9) .0003(7) .0054(8) -.0032(7)
C4 .0165(7) .0230(8) .0208(7) -.0017(7) -.0003(6) .0029(6)
C2' .0225(8) .0258(8) .0214(8) .0043(7) -.0049(7) -.0033(7)
C1'' .0218(7) .0203(7) .0215(7) .0016(7) -.0015(6) -.0004(7)
C4'' .0237(9) .0276(9) .0395(10) .0008(7) .0044(8) .0042(8)
C1' .0236(8) .0226(7) .0184(8) .0025(6) -.0023(6) -.0009(6)
C7'' .0216(9) .0284(9) .0196(8) .0010(7) -.0031(6) -.0043(7)
C7 .0179(8) .0343(10) .0266(9) -.0009(7) .0047(6) -.0029(7)
C3'' .0214(8) .0261(9) .0484(11) -.0019(7) -.0070(8) -.0021(8)
C2'' .0244(8) .0189(8) .0383(10) -.0004(7) -.0066(7) -.0011(7)
C5' .0311(9) .0326(10) .0216(8) .0044(8) .0014(7) -.0027(7)
C6'' .0249(9) .0248(9) .0305(9) -.0049(6) .0011(7) -.0069(7)
C3' .0465(12) .0445(12) .0208(9) .0182(10) -.0073(8) .0022(8)
C4' .0597(14) .0524(13) .0221(9) .0220(12) -.0016(9) -.0026(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 C3 . 1.316(2) yes
N1 C1 . 1.480(2) yes
N1 H1 . .79(3) no
N2 C3 . 1.319(2) yes
N2 C1' . 1.467(2) yes
N2 H2 . .76(2) no
C5 C4 . 1.545(2) yes
C5 C6 . 1.547(2) no
C3 C4 . 1.498(2) yes
C6 C1 . 1.532(2) yes
C1 C7 . 1.531(3) yes
C8 C4 . 1.544(2) yes
C8 C7 . 1.548(3) no
C5'' C4'' . 1.522(3) no
C5'' C6'' . 1.523(2) no
C2' C7'' . 1.525(2) yes
C2' C3' . 1.537(3) yes
C2' C1' . 1.564(2) yes
C1'' C2'' . 1.530(2) no
C1'' C7'' . 1.531(2) yes
C1'' C6'' . 1.533(2) no
C4'' C3'' . 1.523(3) no
C1' C5' . 1.551(2) yes
C3'' C2'' . 1.539(2) no
C5' C4' . 1.525(3) no
C3' C4' . 1.529(3) no