#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008466.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
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_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              806
_journal_page_last               808
_journal_paper_doi               10.1107/S0108270199000402
_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
_chemical_name_systematic
;
(1'R, 2'R)-3-[(cis-2'-Cyclohexylmethylcyclopentyl)imino]-2-azabicyclo[2.2.2]
octan-HBr
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_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_reflns_used    13764
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      3
_cell_volume                     1913.0(8)
_computing_cell_refinement       XDS98
_computing_data_collection       'XDS98 (Kabsch, 1993)'
_computing_data_reduction        XDS98
_computing_molecular_graphics    'CRYSTAN (Burzlaff & Rothammel, 1988)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 6.667
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MAR 180 mm image plate'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24133
_diffrn_reflns_theta_full        25.6
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'approx. spherical (ground)'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          0.0425
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.134
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.006(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0195
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0217P)²+0.4565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0512
_reflns_number_gt                3706
_reflns_number_total             3714
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1314.cif
_cod_data_source_block           struct
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value
'1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.4565P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.4565P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008466
_cod_database_fobs_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_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br- -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C1 115.20(14) yes
C3 N1 H1 121.9(18) no
C1 N1 H1 121.6(18) no
C3 N2 C1' 126.13(16) yes
C3 N2 H2 116.3(16) no
C1' N2 H2 116.2(16) no
C4 C5 C6 109.47(13) no
N1 C3 N2 125.20(16) yes
N1 C3 C4 113.62(14) yes
N2 C3 C4 121.18(15) yes
C1 C6 C5 108.42(14) no
N1 C1 C6 107.54(14) yes
N1 C1 C7 108.23(14) yes
C6 C1 C7 109.57(14) yes
C4 C8 C7 109.09(15) no
C4'' C5'' C6'' 111.67(14) no
C3 C4 C8 106.93(14) yes
C3 C4 C5 108.02(13) yes
C8 C4 C5 108.45(13) yes
C7'' C2' C3' 114.86(15) no
C7'' C2' C1' 114.43(14) yes
C3' C2' C1' 103.57(14) yes
C2'' C1'' C7'' 113.64(14) no
C2'' C1'' C6'' 109.82(13) no
C7'' C1'' C6'' 109.82(13) no
C5'' C4'' C3'' 110.22(15) no
N2 C1' C5' 109.07(14) yes
N2 C1' C2' 113.25(13) yes
C5' C1' C2' 105.58(13) yes
C2' C7'' C1'' 115.47(14) yes
C1 C7 C8 108.80(14) no
C4'' C3'' C2'' 111.78(15) no
C1'' C2'' C3'' 111.84(14) no
C4' C5' C1' 106.09(15) no
C5'' C6'' C1'' 112.46(14) no
C4' C3' C2' 102.87(16) no
C5' C4' C3' 103.99(16) no
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
