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#$Date: 2018-06-08 06:04:35 +0300 (Fri, 08 Jun 2018) $
#$Revision: 208202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/08/4020843.cif $
#------------------------------------------------------------------------------
#
# 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.
#
data_4020843
loop_
_publ_author_name
'M. Heiko Franz'
'Stefanie Röper'
'Rudolf Wartchow'
'H. M. R. Hoffmann'
_publ_section_title
;
  The First and Second Cinchona Rearrangement. Two Fundamental
  Transformations of Alkaloid Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2983
_journal_page_last               2991
_journal_paper_doi               10.1021/jo030363s
_journal_volume                  69
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H20 N2'
_chemical_formula_sum            'C19 H20 N2'
_chemical_formula_weight         276.37
_chemical_name_common            E-Cinchene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.641(2)
_cell_length_b                   10.306(2)
_cell_length_c                   17.176(3)
_cell_measurement_temperature    300(2)
_cell_volume                     1529.6(5)
_diffrn_ambient_temperature      300(2)
_exptl_crystal_density_diffrn    1.200
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-06-08
;
_cod_database_code               4020843
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, z+1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.0150(2) 0.04906(13) 0.23558(7) 0.0500(4) Uani 1 d . .
C2 C 0.0284(2) -0.0148(2) 0.15939(10) 0.0566(5) Uani 1 d . .
H1 H -0.0387(2) -0.0902(2) 0.15850(10) 0.068 Uiso 1 calc R .
H2 H 0.1339(2) -0.0446(2) 0.15239(10) 0.068 Uiso 1 calc R .
C3 C -0.0148(2) 0.0750(2) 0.09163(9) 0.0492(5) Uani 1 d . .
H3 H -0.1205(2) 0.0538(2) 0.07534(9) 0.059 Uiso 1 calc R .
C4 C -0.0152(2) 0.2119(2) 0.12426(9) 0.0516(5) Uani 1 d . .
H4 H -0.0255(2) 0.2755(2) 0.08218(9) 0.062 Uiso 1 calc R .
C5 C -0.1497(2) 0.2231(2) 0.18057(10) 0.0633(6) Uani 1 d . .
H5 H -0.2470(2) 0.2170(2) 0.15259(10) 0.076 Uiso 1 calc R .
H6 H -0.1463(2) 0.3061(2) 0.20711(10) 0.076 Uiso 1 calc R .
C6 C -0.1370(2) 0.1126(2) 0.23960(10) 0.0642(6) Uani 1 d . .
H7 H -0.1530(2) 0.1466(2) 0.29163(10) 0.077 Uiso 1 calc R .
H8 H -0.2174(2) 0.0491(2) 0.22941(10) 0.077 Uiso 1 calc R .
C7 C 0.1347(2) 0.2344(2) 0.16942(10) 0.0554(5) Uani 1 d . .
H9 H 0.2233(2) 0.2136(2) 0.13705(10) 0.066 Uiso 1 calc R .
H10 H 0.1424(2) 0.3246(2) 0.18509(10) 0.066 Uiso 1 calc R .
C8 C 0.1318(2) 0.1483(2) 0.23979(10) 0.0444(5) Uani 1 d . .
C9 C 0.2132(2) 0.1602(2) 0.30500(10) 0.0492(5) Uani 1 d . .
H11 H 0.1950(2) 0.0992(2) 0.34387(10) 0.059 Uiso 1 calc R .
C10 C 0.0884(3) 0.0589(3) 0.02332(13) 0.0904(8) Uani 1 d . .
H12 H 0.1820(3) 0.0195(3) 0.03568(13) 0.109 Uiso 1 calc R .
C11 C 0.0774(4) 0.0852(3) -0.0435(2) 0.166(2) Uani 1 d . .
H13 H -0.0120(4) 0.1250(3) -0.0621(2) 0.199 Uiso 1 calc R .
H14 H 0.1580(4) 0.0662(3) -0.0775(2) 0.199 Uiso 1 calc R .
N1' N 0.5399(2) 0.4657(2) 0.35085(10) 0.0675(5) Uani 1 d . .
C2' C 0.5312(2) 0.4059(2) 0.28375(12) 0.0720(6) Uani 1 d . .
H15 H 0.5977(2) 0.4331(2) 0.24443(12) 0.086 Uiso 1 calc R .
C3' C 0.4299(2) 0.3048(2) 0.26678(10) 0.0610(6) Uani 1 d . .
H16 H 0.4313(2) 0.2672(2) 0.21759(10) 0.073 Uiso 1 calc R .
C4' C 0.3292(2) 0.2606(2) 0.32141(9) 0.0456(4) Uani 1 d . .
C5' C 0.2468(2) 0.2815(2) 0.46068(10) 0.0575(5) Uani 1 d . .
H17 H 0.1751(2) 0.2150(2) 0.45464(10) 0.069 Uiso 1 calc R .
C6' C 0.2610(2) 0.3414(2) 0.53129(11) 0.0682(6) Uani 1 d . .
H18 H 0.2010(2) 0.3143(2) 0.57318(11) 0.082 Uiso 1 calc R .
C7' C 0.3658(2) 0.4434(2) 0.54046(11) 0.0691(6) Uani 1 d . .
H19 H 0.3744(2) 0.4845(2) 0.58846(11) 0.083 Uiso 1 calc R .
C8' C 0.4541(2) 0.4826(2) 0.48071(11) 0.0627(6) Uani 1 d . .
H20 H 0.5224(2) 0.5514(2) 0.48759(11) 0.075 Uiso 1 calc R .
C9' C 0.3389(2) 0.3188(2) 0.39706(10) 0.0444(4) Uani 1 d . .
C10' C 0.4448(2) 0.4210(2) 0.40785(11) 0.0509(5) Uani 1 d . .
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
N1 C8 1.439(2) . ?
N1 C2 1.469(2) . ?
N1 C6 1.470(2) . ?
C2 C3 1.533(2) . ?
C3 C10 1.483(2) . ?
C3 C4 1.518(2) . ?
C4 C5 1.517(2) . ?
C4 C7 1.528(2) . ?
C5 C6 1.529(2) . ?
C7 C8 1.500(2) . ?
C8 C9 1.328(2) . ?
C9 C4' 1.468(2) . ?
C10 C11 1.184(3) . ?
N1' C2' 1.309(2) . ?
N1' C10' 1.359(2) . ?
C2' C3' 1.392(2) . ?
C3' C4' 1.359(2) . ?
C4' C9' 1.433(2) . ?
C5' C6' 1.367(2) . ?
C5' C9' 1.405(2) . ?
C6' C7' 1.395(3) . ?
C7' C8' 1.342(2) . ?
C8' C10' 1.406(2) . ?
C9' C10' 1.408(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21183950
