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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020802.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_4020802
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            'C16 H21 Br2 N O2'
_chemical_formula_weight         419.16
_space_group_IT_number           2
_symmetry_cell_setting           ?
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                106.070(3)
_cell_angle_beta                 111.336(2)
_cell_angle_gamma                102.614(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0331(12)
_cell_length_b                   9.5368(13)
_cell_length_c                   11.1850(16)
_cell_measurement_temperature    110(2)
_cell_volume                     805.77(19)
_diffrn_ambient_temperature      110(2)
_exptl_crystal_density_diffrn    1.728
_cod_database_code               4020802
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
Br1 Br 0.18702(5) 0.62110(5) 0.80054(4) 0.02092(12) Uani 1 d . . .
Br2 Br -0.49508(5) 0.23917(5) 0.37589(4) 0.02060(12) Uani 1 d . . .
O1 O -0.2105(3) 0.4735(3) 0.6836(3) 0.0175(6) Uani 1 d . . .
O2 O 0.2679(3) 0.1688(3) 0.6284(3) 0.0184(6) Uani 1 d . . .
N1 N 0.1030(4) 0.2893(4) 0.6968(3) 0.0128(7) Uani 1 d . . .
C1 C 0.1000(5) 0.2186(4) 0.8034(4) 0.0128(8) Uani 1 d . . .
C2 C -0.0228(4) 0.2678(4) 0.8591(4) 0.0141(8) Uani 1 d . . .
H2A H -0.0128 0.2333 0.9366 0.017 Uiso 1 calc R . .
H2B H 0.0177 0.3833 0.8993 0.017 Uiso 1 calc R . .
C3 C -0.2132(5) 0.2071(5) 0.7556(4) 0.0142(8) Uani 1 d . . .
H3A H -0.2709 0.0996 0.7462 0.017 Uiso 1 calc R . .
C4 C -0.2449(5) 0.2082(4) 0.6097(4) 0.0136(8) Uani 1 d . . .
H4A H -0.2291 0.1225 0.5458 0.016 Uiso 1 calc R . .
C5 C -0.1298(5) 0.3728(4) 0.6543(4) 0.0131(8) Uani 1 d . . .
C6 C 0.0390(5) 0.0393(4) 0.7358(4) 0.0159(9) Uani 1 d . . .
H6A H -0.0814 -0.0022 0.6646 0.019 Uiso 1 calc R . .
H6B H 0.1074 0.0088 0.6883 0.019 Uiso 1 calc R . .
C7 C 0.0356(5) 0.4088(4) 0.6954(4) 0.0136(8) Uani 1 d . . .
C8 C 0.0554(5) -0.0325(5) 0.8447(4) 0.0186(9) Uani 1 d . . .
H8A H -0.0200 -0.0090 0.8871 0.022 Uiso 1 calc R . .
H8B H 0.0183 -0.1474 0.7986 0.022 Uiso 1 calc R . .
C9 C 0.2383(5) 0.0317(5) 0.9588(4) 0.0218(10) Uani 1 d . . .
H9A H 0.3127 0.0023 0.9175 0.026 Uiso 1 calc R . .
H9B H 0.2450 -0.0149 1.0286 0.026 Uiso 1 calc R . .
C10 C 0.3008(5) 0.2103(5) 1.0309(4) 0.0205(10) Uani 1 d . . .
H10A H 0.4220 0.2503 1.1000 0.025 Uiso 1 calc R . .
H10B H 0.2347 0.2391 1.0814 0.025 Uiso 1 calc R . .
C11 C 0.2806(5) 0.2860(5) 0.9240(4) 0.0173(9) Uani 1 d . . .
H11A H 0.3109 0.3997 0.9723 0.021 Uiso 1 calc R . .
H11B H 0.3614 0.2715 0.8853 0.021 Uiso 1 calc R . .
C12 C -0.3059(5) 0.3187(5) 0.7994(4) 0.0188(9) Uani 1 d . . .
H12A H -0.4049 0.2619 0.8078 0.023 Uiso 1 calc R . .
H12B H -0.2273 0.4079 0.8892 0.023 Uiso 1 calc R . .
C13 C -0.3622(5) 0.3736(5) 0.6805(4) 0.0177(9) Uani 1 d . . .
H13A H -0.4521 0.4202 0.6756 0.021 Uiso 1 calc R . .
C14 C -0.4180(5) 0.2240(5) 0.5574(4) 0.0158(9) Uani 1 d . . .
H14A H -0.5045 0.1374 0.5564 0.019 Uiso 1 calc R . .
C15 C 0.1888(5) 0.2563(5) 0.6190(4) 0.0144(9) Uani 1 d . . .
C16 C 0.1759(5) 0.3368(5) 0.5182(4) 0.0190(9) Uani 1 d . . .
H16A H 0.2394 0.3063 0.4670 0.028 Uiso 1 calc R . .
H16B H 0.2238 0.4502 0.5702 0.028 Uiso 1 calc R . .
H16C H 0.0562 0.3058 0.4522 0.028 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
Br1 C7 1.912(4) . ?
Br2 C14 1.950(4) . ?
O1 C5 1.366(5) . ?
O1 C13 1.471(4) . ?
O2 C15 1.214(5) . ?
N1 C15 1.379(5) . ?
N1 C7 1.405(5) . ?
N1 C1 1.529(5) . ?
C1 C11 1.534(5) . ?
C1 C6 1.539(5) . ?
C1 C2 1.552(5) . ?
C2 C3 1.542(5) . ?
C3 C4 1.555(5) . ?
C3 C12 1.573(5) . ?
C4 C5 1.507(5) . ?
C4 C14 1.515(5) . ?
C5 C7 1.323(5) . ?
C6 C8 1.533(5) . ?
C8 C9 1.525(5) . ?
C9 C10 1.536(6) . ?
C10 C11 1.537(5) . ?
C12 C13 1.520(5) . ?
C13 C14 1.509(5) . ?
C15 C16 1.516(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12012916
