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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/2/10/09/2100912.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_2100912
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_sum            'C9 H14 N4 O'
_chemical_formula_weight         194.24
_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                105.520(10)
_cell_angle_beta                 93.880(10)
_cell_angle_gamma                91.790(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6070(10)
_cell_length_b                   8.2157(8)
_cell_length_c                   9.2870(10)
_cell_volume                     483.98(10)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.09
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             208
_cod_data_source_file            ab0288.cif
_cod_data_source_block           ab0288_structure_1_of_2
_cod_original_cell_volume        484.00(10)
_cod_database_code               2100912
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(14) .91270(10) .32410(10) .03970(10) .0467(3)
N(1) 1.3363(2) .2418(2) .43830(10) .0398(3)
N(10) .9175(2) .50990(10) .26050(10) .0412(3)
N(12) .6157(2) .6449(2) .2176(2) .0526(4)
N(13) .7328(2) .4161(2) .03690(10) .0451(3)
C(2) 1.4966(3) .1522(3) .3533(2) .0573(5)
C(3) 1.4282(3) .0795(2) .1857(2) .0519(5)
C(4) 1.2095(2) .1272(2) .15910(10) .0412(4)
C(5) 1.2089(2) .3215(2) .20810(10) .0372(4)
C(6) 1.2806(3) .3822(2) .3780(2) .0473(4)
C(7) 1.1565(3) .1268(3) .4213(2) .0582(6)
C(8) 1.0735(3) .0562(2) .2569(2) .0506(5)
C(9) 1.0097(2) .3894(2) .17560(10) .0361(3)
C(11) .7478(2) .5244(2) .17020(10) .0377(4)
H(21) 1.627(3) .229(2) .371(2) .0711(15)
H(22) 1.532(3) .055(3) .395(2) .0711(15)
H(31) 1.431(3) -.045(3) .156(2) .0711(15)
H(32) 1.515(3) .127(2) .122(2) .0711(15)
H(41) 1.168(3) .083(2) .055(2) .0711(15)
H(51) 1.302(3) .368(2) .147(2) .0711(15)
H(61) 1.395(3) .463(2) .395(2) .0711(15)
H(62) 1.174(3) .442(2) .436(2) .0711(15)
H(71) 1.198(3) .025(2) .467(2) .0711(15)
H(72) 1.055(3) .192(3) .482(2) .0711(15)
H(81) 1.068(3) -.063(3) .231(2) .0711(15)
H(82) .935(3) .092(2) .239(2) .0711(15)
H(121) .507(3) .639(2) .161(2) .0711(15)
H(122) .609(3) .690(3) .315(2) .0711(15)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(13) O(14) C(9) 106.20(10)
C(2) N(1) C(6) 108.90(10)
C(2) N(1) C(7) 109.50(10)
C(6) N(1) C(7) 108.40(10)
C(9) N(10) C(11) 102.90(10)
O(14) N(13) C(11) 102.60(10)
N(1) C(2) C(3) 112.3(2)
C(2) C(3) C(4) 108.50(10)
C(3) C(4) C(5) 107.10(10)
C(3) C(4) C(8) 109.20(10)
C(5) C(4) C(8) 108.80(10)
C(4) C(5) C(6) 108.00(10)
C(4) C(5) C(9) 113.80(10)
C(6) C(5) C(9) 111.60(10)
N(1) C(6) C(5) 112.00(10)
N(1) C(7) C(8) 112.50(10)
C(4) C(8) C(7) 108.4(2)
O(14) C(9) N(10) 113.80(10)
O(14) C(9) C(5) 117.90(10)
N(10) C(9) C(5) 128.30(10)
N(10) C(11) N(12) 121.00(10)
N(10) C(11) N(13) 114.60(10)
N(12) C(11) N(13) 124.40(10)
C(11) N(12) H(121) 116.0(12)
C(11) N(12) H(122) 119.5(14)
H(121) N(12) H(122) 117.4(18)
N(1) C(2) H(21) 110.1(10)
N(1) C(2) H(22) 108.0(11)
C(3) C(2) H(21) 112.8(10)
C(3) C(2) H(22) 107.8(11)
H(21) C(2) H(22) 105.6(15)
C(2) C(3) H(31) 110.9(11)
C(2) C(3) H(32) 111.3(11)
C(4) C(3) H(31) 108.2(12)
C(4) C(3) H(32) 108.4(11)
H(31) C(3) H(32) 109.6(15)
C(3) C(4) H(41) 108.3(12)
C(5) C(4) H(41) 111.5(10)
C(8) C(4) H(41) 111.7(11)
C(4) C(5) H(51) 108.8(10)
C(6) C(5) H(51) 111.2(11)
C(9) C(5) H(51) 103.3(11)
N(1) C(6) H(61) 109.2(11)
N(1) C(6) H(62) 108.4(10)
C(5) C(6) H(61) 110.6(11)
C(5) C(6) H(62) 110.9(11)
H(61) C(6) H(62) 105.6(15)
N(1) C(7) H(71) 108.0(11)
N(1) C(7) H(72) 106.3(13)
C(8) C(7) H(71) 109.7(10)
C(8) C(7) H(72) 111.3(11)
H(71) C(7) H(72) 108.9(17)
C(4) C(8) H(81) 112.2(12)
C(4) C(8) H(82) 107.0(10)
C(7) C(8) H(81) 109.7(11)
C(7) C(8) H(82) 111.9(10)
H(81) C(8) H(82) 107.7(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(14) N(13) 1.431(2)
O(14) C(9) 1.340(2)
N(1) C(2) 1.462(2)
N(1) C(6) 1.457(2)
N(1) C(7) 1.467(2)
N(10) C(9) 1.288(2)
N(10) C(11) 1.382(2)
N(12) C(11) 1.345(2)
N(13) C(11) 1.312(2)
C(2) C(3) 1.540(2)
C(3) C(4) 1.530(2)
C(4) C(5) 1.539(2)
C(4) C(8) 1.527(2)
C(5) C(6) 1.558(2)
C(5) C(9) 1.489(2)
C(7) C(8) 1.537(2)
N(12) H(121) 0.853(19)
N(12) H(122) 0.886(18)
C(2) H(21) 1.029(19)
C(2) H(22) 1.00(2)
C(3) H(31) 0.99(2)
C(3) H(32) 0.993(19)
C(4) H(41) 0.955(18)
C(5) H(51) 0.997(19)
C(6) H(61) 0.966(19)
C(6) H(62) 0.979(19)
C(7) H(71) 1.069(18)
C(7) H(72) 0.98(2)
C(8) H(81) 0.94(2)
C(8) H(82) 0.99(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 92136287
