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#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020803.cif $
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#
# 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.
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data_4020803
loop_
_publ_author_name
'Fedor I. Zubkov'
'Eugenia V. Nikitina'
'Konstantin F. Turchin'
'Grigorii G. Aleksandrov'
'Anastasia A. Safronova'
'Roman S. Borisov'
'Alexey V. Varlamov'
_publ_section_title
;
 Wagner-Meerwein Skeletal Rearrangement of
 3-Spiroannulated 6,8a-Epoxy- and 6,8a;7,8-Diepoxyisoquinolines
 (3-Aza-11-oxatricyclo[6.2.1.0^1,6^]undec-9-enes).
 Isolation and Identification of
 5-Aza-2-oxatricyclo[6.2.1.0^3,9^]undec-3-enes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              432
_journal_page_last               438
_journal_paper_doi               10.1021/jo0353684
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C18 H25 N O4'
_chemical_formula_weight         319.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                112.099(3)
_cell_angle_beta                 101.216(4)
_cell_angle_gamma                96.596(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1726(17)
_cell_length_b                   9.9030(19)
_cell_length_c                   10.0782(19)
_cell_measurement_temperature    110(2)
_cell_volume                     814.0(3)
_diffrn_ambient_temperature      110(2)
_exptl_crystal_density_diffrn    1.303
_cod_database_code               4020803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61058(16) 0.10937(14) 0.66632(15) 0.0213(3) Uani 1 d . . .
O2 O 0.35306(17) 0.63970(15) 0.73885(18) 0.0273(4) Uani 1 d . . .
O3 O 0.73455(16) 0.21377(15) 0.96643(16) 0.0236(3) Uani 1 d . . .
O4 O 0.77557(19) 0.01689(17) 1.01648(19) 0.0312(4) Uani 1 d . . .
N1 N 0.40688(18) 0.40807(17) 0.69005(19) 0.0190(4) Uani 1 d . . .
C1 C 0.2452(2) 0.3288(2) 0.6652(2) 0.0186(4) Uani 1 d . . .
C2 C 0.2411(2) 0.1632(2) 0.6339(2) 0.0199(4) Uani 1 d . . .
H2A H 0.1335 0.1129 0.6079 0.024 Uiso 1 calc R . .
H2B H 0.2794 0.1188 0.5450 0.024 Uiso 1 calc R . .
C3 C 0.3301(2) 0.12464(19) 0.7566(2) 0.0194(4) Uani 1 d . . .
H3A H 0.2674 0.1212 0.8266 0.023 Uiso 1 calc R . .
C4 C 0.4864(2) 0.23304(19) 0.8429(2) 0.0188(4) Uani 1 d . . .
H4A H 0.4845 0.3325 0.9192 0.023 Uiso 1 calc R . .
C5 C 0.5493(2) 0.2333(2) 0.7163(2) 0.0196(4) Uani 1 d . . .
C6 C 0.5129(2) 0.3163(2) 0.6431(2) 0.0211(4) Uani 1 d . . .
H6A H 0.5548 0.3150 0.5636 0.025 Uiso 1 calc R . .
C7 C 0.1848(2) 0.4036(2) 0.8014(2) 0.0222(4) Uani 1 d . . .
H7A H 0.2410 0.3858 0.8855 0.027 Uiso 1 calc R . .
H7B H 0.2035 0.5125 0.8298 0.027 Uiso 1 calc R . .
C8 C 0.0143(2) 0.3445(2) 0.7717(3) 0.0257(4) Uani 1 d . . .
H8A H -0.0031 0.2384 0.7557 0.031 Uiso 1 calc R . .
H8B H -0.0209 0.4005 0.8597 0.031 Uiso 1 calc R . .
C9 C -0.0772(2) 0.3594(2) 0.6371(3) 0.0281(5) Uani 1 d . . .
H9A H -0.0679 0.4663 0.6572 0.034 Uiso 1 calc R . .
H9B H -0.1858 0.3163 0.6190 0.034 Uiso 1 calc R . .
C10 C -0.0236(2) 0.2810(2) 0.4991(2) 0.0258(5) Uani 1 d . . .
H10A H -0.0803 0.2997 0.4157 0.031 Uiso 1 calc R . .
H10B H -0.0448 0.1722 0.4713 0.031 Uiso 1 calc R . .
C11 C 0.1469(2) 0.3368(2) 0.5266(2) 0.0209(4) Uani 1 d . . .
H11A H 0.1646 0.4415 0.5376 0.025 Uiso 1 calc R . .
H11B H 0.1801 0.2769 0.4388 0.025 Uiso 1 calc R . .
C12 C 0.3828(2) -0.0266(2) 0.6902(2) 0.0221(4) Uani 1 d . . .
H12A H 0.3445 -0.0975 0.7294 0.027 Uiso 1 calc R . .
H12B H 0.3473 -0.0727 0.5806 0.027 Uiso 1 calc R . .
C13 C 0.5556(2) 0.0192(2) 0.7414(2) 0.0215(4) Uani 1 d . . .
H13A H 0.6085 -0.0647 0.7366 0.026 Uiso 1 calc R . .
C14 C 0.5782(2) 0.1372(2) 0.8970(2) 0.0207(4) Uani 1 d . . .
H14A H 0.5313 0.0987 0.9609 0.025 Uiso 1 calc R . .
C15 C 0.4444(2) 0.5579(2) 0.7265(2) 0.0233(4) Uani 1 d . . .
C16 C 0.6111(3) 0.6200(2) 0.7523(3) 0.0328(5) Uani 1 d . . .
H16A H 0.6266 0.7271 0.7772 0.049 Uiso 1 calc R . .
H16B H 0.6435 0.5699 0.6621 0.049 Uiso 1 calc R . .
H16C H 0.6710 0.6030 0.8341 0.049 Uiso 1 calc R . .
C17 C 0.8228(2) 0.1387(2) 1.0223(2) 0.0235(4) Uani 1 d . . .
C18 C 0.9839(3) 0.2223(2) 1.0884(3) 0.0303(5) Uani 1 d . . .
H18A H 1.0447 0.1638 1.1273 0.046 Uiso 1 calc R . .
H18B H 0.9881 0.3179 1.1692 0.046 Uiso 1 calc R . .
H18C H 1.0247 0.2401 1.0122 0.046 Uiso 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.371(2) . ?
O1 C13 1.475(2) . ?
O2 C15 1.222(3) . ?
O3 C17 1.342(2) . ?
O3 C14 1.443(2) . ?
O4 C17 1.209(3) . ?
N1 C15 1.370(2) . ?
N1 C6 1.433(3) . ?
N1 C1 1.523(2) . ?
C1 C7 1.538(3) . ?
C1 C11 1.543(3) . ?
C1 C2 1.544(3) . ?
C2 C3 1.541(3) . ?
C3 C4 1.556(3) . ?
C3 C12 1.569(3) . ?
C4 C5 1.501(3) . ?
C4 C14 1.517(3) . ?
C5 C6 1.325(3) . ?
C7 C8 1.534(3) . ?
C8 C9 1.518(3) . ?
C9 C10 1.524(3) . ?
C10 C11 1.532(3) . ?
C12 C13 1.525(3) . ?
C13 C14 1.519(3) . ?
C15 C16 1.515(3) . ?
C17 C18 1.495(3) . ?
