#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/08/4020844.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_4020844
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 sy
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.827(2)
_cell_length_b                   13.885(3)
_cell_length_c                   8.545(3)
_cell_measurement_temperature    300(2)
_cell_volume                     809.9(4)
_diffrn_ambient_temperature      300(2)
_exptl_crystal_density_diffrn    1.207
_cod_original_sg_symbol_Hall     P_2yb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O -0.1764(2) 0.35747(9) 0.31064(14) 0.0607(3) Uani 1 d D .
H1 H -0.1206(31) 0.4184(10) 0.3489(28) 0.134(10) Uiso 1 d D .
N1 N 0.2581(2) 0.25052(10) 0.10962(15) 0.0482(3) Uani 1 d . .
C2 C 0.1312(2) 0.28281(11) 0.2375(2) 0.0402(4) Uani 1 d . .
H2 H 0.2008(2) 0.33514(11) 0.2913(2) 0.048 Uiso 1 calc R .
C3 C -0.0655(2) 0.32384(12) 0.1823(2) 0.0439(4) Uani 1 d . .
H3 H -0.1393(2) 0.27097(12) 0.1337(2) 0.053 Uiso 1 calc R .
C4 C -0.0377(2) 0.40097(13) 0.0574(2) 0.0531(5) Uani 1 d . .
H4 H 0.0376(2) 0.45342(13) 0.1029(2) 0.064 Uiso 1 calc R .
H5 H -0.1654(2) 0.42636(13) 0.0282(2) 0.064 Uiso 1 calc R .
C5 C 0.0658(2) 0.36715(14) -0.0927(2) 0.0541(4) Uani 1 d . .
H6 H 0.0102(2) 0.40364(14) -0.1808(2) 0.065 Uiso 1 calc R .
C6 C 0.2893(2) 0.38225(13) -0.0928(2) 0.0538(5) Uani 1 d . .
H7 H 0.3372(2) 0.35419(13) -0.1904(2) 0.065 Uiso 1 calc R .
C7 C 0.3832(2) 0.32421(15) 0.0415(2) 0.0611(5) Uani 1 d . .
H8 H 0.5007(2) 0.29345(15) 0.0031(2) 0.073 Uiso 1 calc R .
H9 H 0.4227(2) 0.36863(15) 0.1236(2) 0.073 Uiso 1 calc R .
C8 C 0.1551(3) 0.19692(14) -0.0139(2) 0.0637(5) Uani 1 d . .
H10 H 0.0705(3) 0.14966(14) 0.0344(2) 0.076 Uiso 1 calc R .
H11 H 0.2508(3) 0.16224(14) -0.0751(2) 0.076 Uiso 1 calc R .
C9 C 0.0304(3) 0.2601(2) -0.1252(2) 0.0680(6) Uani 1 d . .
H12 H 0.0636(3) 0.2458(2) -0.2328(2) 0.082 Uiso 1 calc R .
H13 H -0.1072(3) 0.2455(2) -0.1114(2) 0.082 Uiso 1 calc R .
C10 C 0.3581(3) 0.4845(2) -0.0892(2) 0.0702(6) Uani 1 d . .
H14 H 0.3061(3) 0.5246(2) -0.0131(2) 0.084 Uiso 1 calc R .
C11 C 0.4860(3) 0.5222(2) -0.1850(3) 0.0945(8) Uani 1 d . .
H15 H 0.5413(3) 0.4845(2) -0.2628(3) 0.113 Uiso 1 calc R .
H16 H 0.5212(3) 0.5866(2) -0.1751(3) 0.113 Uiso 1 calc R .
N1' N 0.1051(2) 0.03736(10) 0.5535(2) 0.0536(4) Uani 1 d . .
C2' C -0.0365(3) 0.05793(14) 0.4542(2) 0.0590(5) Uani 1 d . .
H17 H -0.1434(3) 0.01646(14) 0.4491(2) 0.071 Uiso 1 calc R .
C3' C -0.0375(2) 0.13839(13) 0.3551(2) 0.0530(4) Uani 1 d . .
H18 H -0.1451(2) 0.14967(13) 0.2898(2) 0.064 Uiso 1 calc R .
C4' C 0.1172(2) 0.20018(11) 0.3534(2) 0.0406(4) Uani 1 d . .
C5' C 0.4465(2) 0.23891(13) 0.4735(2) 0.0483(4) Uani 1 d . .
H19 H 0.4593(2) 0.29275(13) 0.4097(2) 0.058 Uiso 1 calc R .
C6' C 0.5917(2) 0.21675(14) 0.5785(2) 0.0599(5) Uani 1 d . .
H20 H 0.7016(2) 0.25608(14) 0.5867(2) 0.072 Uiso 1 calc R .
C7' C 0.5766(3) 0.1357(2) 0.6734(2) 0.0625(5) Uani 1 d . .
H21 H 0.6766(3) 0.1214(2) 0.7445(2) 0.075 Uiso 1 calc R .
C8' C 0.4169(3) 0.07708(14) 0.6635(2) 0.0558(5) Uani 1 d . .
H22 H 0.4094(3) 0.02265(14) 0.7266(2) 0.067 Uiso 1 calc R .
C9' C 0.2625(2) 0.09886(11) 0.5575(2) 0.0450(4) Uani 1 d . .
C10' C 0.2761(2) 0.18090(12) 0.4604(2) 0.0413(4) 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
O1 C3 1.419(2) . ?
N1 C7 1.458(2) . ?
N1 C8 1.464(2) . ?
N1 C2 1.473(2) . ?
C2 C4' 1.519(2) . ?
C2 C3 1.527(2) . ?
C3 C4 1.526(2) . ?
C4 C5 1.545(2) . ?
C5 C9 1.530(3) . ?
C5 C6 1.540(2) . ?
C6 C10 1.496(3) . ?
C6 C7 1.536(2) . ?
C8 C9 1.543(3) . ?
C10 C11 1.313(3) . ?
N1' C2' 1.310(2) . ?
N1' C9' 1.373(2) . ?
C2' C3' 1.402(3) . ?
C3' C4' 1.361(2) . ?
C4' C10' 1.435(2) . ?
C5' C6' 1.364(2) . ?
C5' C10' 1.418(2) . ?
C6' C7' 1.392(3) . ?
C7' C8' 1.362(2) . ?
C8' C9' 1.414(2) . ?
C9' C10' 1.413(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21183949
