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#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/09/2100913.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_2100913
loop_
_publ_author_name
'Kooijman, H.'
'Kanters, J. A.'
'Kroon, J.'
'Kelder, J.'
_publ_section_title
;
 Structure and conformation of the muscarinic agonists
 3-(3-amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo[2.2.2]octane and
 1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxaldehyde oxime and related
 tertiary amine, quaternary ammonium and sulfonium analogues
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              356
_journal_page_last               366
_journal_paper_doi               10.1107/S0108768192008383
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C7 H13 N2 O1,Cl'
_chemical_formula_sum            'C7 H13 Cl N2 O'
_chemical_formula_weight         176.64
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                89.72(3)
_cell_angle_beta                 87.78(4)
_cell_angle_gamma                75.69(4)
_cell_formula_units_Z            2
_cell_length_a                   6.843(3)
_cell_length_b                   6.997(3)
_cell_length_c                   9.837(4)
_cell_volume                     456.0(3)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.37
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             188
_cod_data_source_file            ab0288.cif
_cod_data_source_block           ab0288_structure_2_of_2
_cod_original_formula_sum        'C7 H13 Cl N2 O1'
_cod_database_code               2100913
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(10) .3658(2) .7037(2) .24060(10) .0561(4)
N(1) .1821(2) .7197(2) -.31290(10) .0382(3)
N(9) .3420(2) .7261(2) .09930(10) .0435(4)
C(2) .3269(3) .7491(3) -.4229(2) .0522(5)
C(3) -.0284(3) .8387(2) -.3342(2) .0467(4)
C(4) -.1728(3) .7754(3) -.2337(2) .0501(5)
C(5) -.0938(3) .7508(2) -.0938(2) .0437(4)
C(6) .0966(2) .7457(2) -.06740(10) .0356(4)
C(7) .2515(2) .7597(2) -.17640(10) .0374(4)
C(8) .1622(2) .7253(2) .0724(2) .0403(4)
Cl(1) .22435(6) .27513(5) .66177(4) .04740(10)
H(11) .17538 .59836 -.31203 .0529
H(21) .27434 .71682 -.50689 .071
H(22) .32163 .89020 -.42093 .071
H(23) .45756 .65258 -.41014 .071
H(31) -.06149 .8224 -.43057 .0529
H(32) -.02814 .97964 -.32070 .0529
H(41) -.2996 .87827 -.23121 .0529
H(42) -.19636 .65015 -.26863 .0529
H(51) -.17560 .72834 -.02212 .0529
H(71) .2773 .89027 -.17709 .0529
H(72) .37649 .65641 -.15971 .0529
H(81) .07515 .71060 .14066 .0529
H(101) .48604 .71967 .25382 .071
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) N(1) C(3) 112.40(10)
C(2) N(1) C(7) 111.20(10)
C(3) N(1) C(7) 111.20(10)
O(10) N(9) C(8) 109.20(10)
N(1) C(3) C(4) 109.60(10)
C(3) C(4) C(5) 112.1(2)
C(4) C(5) C(6) 123.0(2)
C(5) C(6) C(7) 122.80(10)
C(5) C(6) C(8) 120.00(10)
C(7) C(6) C(8) 117.20(10)
N(1) C(7) C(6) 110.70(10)
N(9) C(8) C(6) 120.60(10)
N(9) O(10) H(101) 104.89(4)
C(2) N(1) H(11) 109.75(4)
C(3) N(1) H(11) 105.69(4)
C(7) N(1) H(11) 106.22(4)
N(1) C(2) H(21) 106.26(4)
N(1) C(2) H(22) 105.29(4)
N(1) C(2) H(23) 108.29(4)
H(21) C(2) H(22) 109.50(4)
H(21) C(2) H(23) 107.70(4)
H(22) C(2) H(23) 119.11(4)
N(1) C(3) H(31) 108.57(4)
N(1) C(3) H(32) 106.84(4)
C(4) C(3) H(31) 112.69(4)
C(4) C(3) H(32) 111.37(4)
H(31) C(3) H(32) 107.59(4)
C(3) C(4) H(41) 107.76(4)
C(3) C(4) H(42) 107.16(4)
C(5) C(4) H(41) 108.59(4)
C(5) C(4) H(42) 111.35(4)
H(41) C(4) H(42) 109.77(4)
C(4) C(5) H(51) 119.73(4)
C(6) C(5) H(51) 117.04(4)
N(1) C(7) H(71) 108.67(4)
N(1) C(7) H(72) 107.35(4)
C(6) C(7) H(71) 110.71(4)
C(6) C(7) H(72) 108.30(4)
H(71) C(7) H(72) 111.08(4)
N(9) C(8) H(81) 119.34(4)
C(6) C(8) H(81) 120.04(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(10) N(9) 1.410(2)
N(1) C(2) 1.487(2)
N(1) C(3) 1.497(2)
N(1) C(7) 1.492(2)
N(9) C(8) 1.270(2)
C(3) C(4) 1.512(3)
C(4) C(5) 1.492(3)
C(5) C(6) 1.330(3)
C(6) C(7) 1.498(2)
C(6) C(8) 1.458(2)
O(10) H(101) 0.8717(4)
N(1) H(11) 0.8613(4)
C(2) H(21) 0.9636(4)
C(2) H(22) 0.9789(4)
C(2) H(23) 0.9903(4)
C(3) H(31) 0.9966(4)
C(3) H(32) 0.9962(4)
C(4) H(41) 0.9804(4)
C(4) H(42) 0.9947(4)
C(5) H(51) 0.9204(4)
C(7) H(71) 0.9727(4)
C(7) H(72) 0.9922(4)
C(8) H(81) 0.9029(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063153
