#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/11/4021111.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_4021111
loop_
_publ_author_name
'Chi-Lik Ken Lee'
'Hui Yvonne Ling'
'Teck-Peng Loh'
_publ_section_title
;
 Asymmetric Synthesis of C-Aliphatic Homoallylic Amines
 and Biologically Important Cyclohexenylamine Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7787
_journal_page_last               7789
_journal_paper_doi               10.1021/jo048903o
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C21 H23 Br2 N O2'
_chemical_formula_weight         481.22
_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                94.398(10)
_cell_angle_beta                 97.815(10)
_cell_angle_gamma                110.743(9)
_cell_formula_units_Z            2
_cell_length_a                   9.669(5)
_cell_length_b                   10.054(5)
_cell_length_c                   11.307(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1009.0(9)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.584
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4021111
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.25560(3) 0.34529(2) 0.402796(18) 0.04877(8) Uani 1 1 d . . .
Br2 Br 0.17605(2) -0.03945(2) 0.61676(2) 0.04603(7) Uani 1 1 d . . .
O1 O 0.74194(18) 0.15179(19) 0.86449(15) 0.0595(4) Uani 1 1 d . . .
O2 O 0.92270(16) 0.13817(16) 0.76746(13) 0.0455(3) Uani 1 1 d . . .
N1 N 0.66466(16) 0.32480(16) 0.70279(15) 0.0332(3) Uani 1 1 d . . .
H1A H 0.657(3) 0.327(3) 0.773(2) 0.052(7) Uiso 1 1 d . . .
C1 C 1.0380(2) 0.4579(3) 0.6479(2) 0.0522(5) Uani 1 1 d . . .
H1 H 1.012(3) 0.402(3) 0.571(3) 0.073(9) Uiso 1 1 d . . .
C2 C 1.1636(3) 0.5808(4) 0.6709(4) 0.0807(10) Uani 1 1 d . . .
H2 H 1.234(4) 0.606(4) 0.616(3) 0.095(10) Uiso 1 1 d . . .
C3 C 1.1947(3) 0.6707(3) 0.7728(4) 0.0871(11) Uani 1 1 d . . .
H3 H 1.296(4) 0.759(4) 0.796(3) 0.110(11) Uiso 1 1 d . . .
C4 C 1.0997(4) 0.6411(3) 0.8550(3) 0.0861(10) Uani 1 1 d . . .
H4 H 1.099(4) 0.694(3) 0.915(3) 0.086(10) Uiso 1 1 d . . .
C5 C 0.9695(3) 0.5169(3) 0.8323(2) 0.0606(6) Uani 1 1 d . . .
H5 H 0.903(3) 0.500(3) 0.880(2) 0.054(7) Uiso 1 1 d . . .
C6 C 0.93895(19) 0.42599(19) 0.72856(16) 0.0346(4) Uani 1 1 d . . .
C7 C 0.79899(18) 0.29049(19) 0.70049(16) 0.0299(3) Uani 1 1 d . . .
H7 H 0.7960(19) 0.2438(18) 0.6207(16) 0.022(4) Uiso 1 1 d . . .
C8 C 0.81439(19) 0.18556(19) 0.78723(16) 0.0337(4) Uani 1 1 d . . .
C9 C 0.9590(3) 0.0500(3) 0.8526(3) 0.0566(6) Uani 1 1 d . . .
H9A H 1.052(4) 0.047(3) 0.841(3) 0.094(10) Uiso 1 1 d . . .
H9B H 0.985(4) 0.102(4) 0.933(4) 0.111(13) Uiso 1 1 d . . .
H9C H 0.883(4) -0.025(4) 0.859(3) 0.094(11) Uiso 1 1 d . . .
C10 C 0.52492(17) 0.21779(18) 0.63379(15) 0.0279(3) Uani 1 1 d . . .
C11 C 0.52849(19) 0.2238(2) 0.49951(16) 0.0326(4) Uani 1 1 d . . .
H11A H 0.551(2) 0.317(2) 0.4870(18) 0.036(5) Uiso 1 1 d . . .
H11B H 0.605(2) 0.194(2) 0.4779(19) 0.042(5) Uiso 1 1 d . . .
C12 C 0.3823(2) 0.1280(2) 0.42063(18) 0.0348(4) Uani 1 1 d . . .
H12A H 0.385(2) 0.136(2) 0.340(2) 0.046(6) Uiso 1 1 d . . .
H12B H 0.364(2) 0.031(2) 0.4329(18) 0.039(5) Uiso 1 1 d . . .
C13 C 0.2486(2) 0.15922(19) 0.45321(17) 0.0340(4) Uani 1 1 d . . .
H13 H 0.163(2) 0.095(2) 0.4066(18) 0.034(5) Uiso 1 1 d . . .
C14 C 0.24385(19) 0.16439(18) 0.58614(16) 0.0317(4) Uani 1 1 d . . .
H14 H 0.166(2) 0.192(2) 0.6065(18) 0.038(5) Uiso 1 1 d . . .
C15 C 0.39300(18) 0.25570(18) 0.66748(15) 0.0286(3) Uani 1 1 d . . .
H15 H 0.410(2) 0.350(2) 0.6487(17) 0.036(5) Uiso 1 1 d . . .
C16 C 0.37956(19) 0.2605(2) 0.79957(16) 0.0356(4) Uani 1 1 d . . .
C17 C 0.4096(3) 0.1653(3) 0.8719(2) 0.0520(5) Uani 1 1 d . . .
H10 H 0.511(2) 0.1207(19) 0.6505(15) 0.025(4) Uiso 1 1 d . . .
H17 H 0.442(3) 0.098(3) 0.838(2) 0.057(7) Uiso 1 1 d . . .
C18 C 0.3929(3) 0.1749(4) 0.9924(2) 0.0709(8) Uani 1 1 d . . .
H18 H 0.420(3) 0.119(3) 1.039(3) 0.080(9) Uiso 1 1 d . . .
C19 C 0.3471(3) 0.2772(4) 1.0406(3) 0.0767(9) Uani 1 1 d . . .
H19 H 0.339(4) 0.280(3) 1.122(3) 0.095(10) Uiso 1 1 d . . .
C20 C 0.3170(4) 0.3710(4) 0.9709(3) 0.0752(8) Uani 1 1 d . . .
H20 H 0.297(4) 0.441(4) 0.999(3) 0.093(11) Uiso 1 1 d . . .
C21 C 0.3336(3) 0.3639(3) 0.8510(2) 0.0519(5) Uani 1 1 d . . .
H21 H 0.315(3) 0.430(3) 0.804(2) 0.055(7) Uiso 1 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
Br1 C13 1.978(2) . ?
Br2 C14 1.9920(19) . ?
O1 C8 1.188(2) . ?
O2 C8 1.332(2) . ?
O2 C9 1.447(3) . ?
N1 C7 1.460(2) . ?
N1 C10 1.465(2) . ?
C1 C2 1.368(4) . ?
C1 C6 1.384(3) . ?
C2 C3 1.337(5) . ?
C3 C4 1.370(5) . ?
C4 C5 1.400(4) . ?
C5 C6 1.359(3) . ?
C6 C7 1.516(2) . ?
C7 C8 1.525(2) . ?
C10 C11 1.529(3) . ?
C10 C15 1.540(2) . ?
C11 C12 1.511(3) . ?
C12 C13 1.519(3) . ?
C13 C14 1.507(3) . ?
C14 C15 1.530(2) . ?
C15 C16 1.515(3) . ?
C16 C21 1.386(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.362(5) . ?
C19 C20 1.357(5) . ?
C20 C21 1.386(4) . ?
