#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/11/4021110.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_4021110
loop_
_publ_author_name
'Naoki Kise'
'Kengo Ohya'
'Kie Arimoto'
'Yutaka Yamashita'
'Yuuki Hirano'
'Tadahiro Ono'
'Nasuo Ueda'
_publ_section_title
;
 Electroreductive Intramolecular Coupling of Aromatic β- and
 γ-Imino Esters: A New Synthetic Method for
 N-Alkoxycarbonyl-2-aryl-3-ones and cis-2-Aryl-3-ols
 of Pyrrolidines and Piperidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7710
_journal_page_last               7719
_journal_paper_doi               10.1021/jo0488917
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C14 H19 N O4 '
_chemical_formula_sum            'C14 H19 N O4'
_chemical_formula_weight         265.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.305(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.717(2)
_cell_length_b                   9.665(2)
_cell_length_c                   14.758(3)
_cell_measurement_temperature    296.1
_cell_volume                     1336.8(4)
_exptl_crystal_density_diffrn    1.318
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H19 N O4 '
_cod_database_code               4021110
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,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_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
O(1) O 0.2144(1) 0.2034(1) 0.95111(7) 0.0462(3) Uani 1.00 1 d . . .
O(2) O 0.6348(1) -0.0390(1) 0.89428(7) 0.0439(3) Uani 1.00 1 d . . .
O(3) O 0.7547(1) 0.1351(1) 0.84777(8) 0.0542(3) Uani 1.00 1 d . . .
O(4) O 0.2368(1) -0.1019(1) 0.89560(7) 0.0557(3) Uani 1.00 1 d . . .
N(1) N 0.5317(1) 0.1727(1) 0.85721(8) 0.0368(3) Uani 1.00 1 d . . .
C(1) C 0.4000(1) 0.1253(1) 0.87939(9) 0.0332(4) Uani 1.00 1 d . . .
C(2) C 0.3468(1) 0.2406(1) 0.9339(1) 0.0369(4) Uani 1.00 1 d . . .
C(3) C 0.3313(2) 0.3771(2) 0.8828(1) 0.0444(4) Uani 1.00 1 d . . .
C(4) C 0.4761(2) 0.4209(2) 0.8720(1) 0.0502(5) Uani 1.00 1 d . . .
C(5) C 0.5416(2) 0.3141(1) 0.8210(1) 0.0440(4) Uani 1.00 1 d . . .
C(6) C 0.2858(1) 0.0705(1) 0.79513(9) 0.0352(4) Uani 1.00 1 d . . .
C(7) C 0.2058(1) -0.0452(1) 0.8068(1) 0.0406(4) Uani 1.00 1 d . . .
C(8) C 0.1004(2) -0.0979(2) 0.7320(1) 0.0494(5) Uani 1.00 1 d . . .
C(9) C 0.0752(2) -0.0376(2) 0.6443(1) 0.0569(5) Uani 1.00 1 d . . .
C(10) C 0.1532(2) 0.0747(2) 0.6308(1) 0.0555(5) Uani 1.00 1 d . . .
C(11) C 0.2571(2) 0.1285(2) 0.7060(1) 0.0445(4) Uani 1.00 1 d . . .
C(12) C 0.1913(3) -0.2364(2) 0.9058(2) 0.0846(8) Uani 1.00 1 d . . .
C(13) C 0.6391(1) 0.0804(1) 0.86859(9) 0.0357(4) Uani 1.00 1 d . . .
C(14) C 0.8793(2) 0.0490(3) 0.8666(2) 0.0679(7) Uani 1.00 1 d . . .
H(1) H 0.428(1) 0.050(1) 0.9212(9) 0.030(3) Uiso 1.00 1 c . . .
H(2) H 0.422(1) 0.250(1) 0.9947(9) 0.036(4) Uiso 1.00 1 c . . .
H(3) H 0.295(2) 0.441(2) 0.918(1) 0.049(4) Uiso 1.00 1 c . . .
H(4) H 0.260(2) 0.366(2) 0.820(1) 0.050(4) Uiso 1.00 1 c . . .
H(5) H 0.542(2) 0.434(2) 0.936(1) 0.058(5) Uiso 1.00 1 c . . .
H(6) H 0.469(2) 0.508(2) 0.837(1) 0.066(5) Uiso 1.00 1 c . . .
H(7) H 0.643(2) 0.333(2) 0.830(1) 0.052(4) Uiso 1.00 1 c . . .
H(8) H 0.493(2) 0.315(2) 0.753(1) 0.048(4) Uiso 1.00 1 c . . .
H(9) H 0.052(2) -0.177(2) 0.745(1) 0.055(5) Uiso 1.00 1 c . . .
H(10) H 0.001(2) -0.078(2) 0.592(1) 0.063(5) Uiso 1.00 1 c . . .
H(11) H 0.141(2) 0.119(2) 0.573(1) 0.061(5) Uiso 1.00 1 c . . .
H(12) H 0.311(2) 0.207(2) 0.696(1) 0.051(4) Uiso 1.00 1 c . . .
H(13) H 0.077(3) -0.239(3) 0.884(2) 0.16(1) Uiso 1.00 1 c . . .
H(14) H 0.226(2) -0.263(2) 0.968(2) 0.081(6) Uiso 1.00 1 c . . .
H(15) H 0.216(3) -0.293(3) 0.865(2) 0.107(9) Uiso 1.00 1 c . . .
H(16) H 0.952(3) 0.099(3) 0.854(2) 0.111(8) Uiso 1.00 1 c . . .
H(17) H 0.860(3) -0.047(3) 0.847(2) 0.13(1) Uiso 1.00 1 c . . .
H(18) H 0.901(3) 0.027(3) 0.933(2) 0.13(1) Uiso 1.00 1 c . . .
H(19) H 0.233(2) 0.136(2) 0.995(1) 0.084(7) Uiso 1.00 1 c . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O(1) C(2) 1.421(2) yes . .
O(1) H(19) 0.90(2) no . .
O(2) C(13) 1.218(2) yes . .
O(3) C(13) 1.348(2) yes . .
O(3) C(14) 1.435(2) yes . .
O(4) C(7) 1.379(2) yes . .
O(4) C(12) 1.394(3) yes . .
N(1) C(1) 1.475(2) yes . .
N(1) C(5) 1.480(2) yes . .
N(1) C(13) 1.350(2) yes . .
C(1) C(2) 1.541(2) yes . .
C(1) C(6) 1.526(2) yes . .
C(1) H(1) 0.95(1) no . .
C(2) C(3) 1.507(2) yes . .
C(2) H(2) 1.00(1) no . .
C(3) C(4) 1.517(3) yes . .
C(3) H(3) 0.94(2) no . .
C(3) H(4) 1.01(1) no . .
C(4) C(5) 1.514(3) yes . .
C(4) H(5) 0.99(2) no . .
C(4) H(6) 0.98(2) no . .
C(5) H(7) 0.98(2) no . .
C(5) H(8) 0.99(2) no . .
C(6) C(7) 1.398(2) yes . .
C(6) C(11) 1.389(2) yes . .
C(7) C(8) 1.389(2) yes . .
C(8) C(9) 1.381(2) yes . .
C(8) H(9) 0.95(2) no . .
C(9) C(10) 1.368(3) yes . .
C(9) H(10) 0.98(2) no . .
C(10) C(11) 1.389(2) yes . .
C(10) H(11) 0.93(2) no . .
C(11) H(12) 0.95(2) no . .
C(12) H(13) 1.07(3) no . .
C(12) H(14) 0.92(2) no . .
C(12) H(15) 0.88(3) no . .
C(14) H(16) 0.91(3) no . .
C(14) H(17) 0.97(3) no . .
C(14) H(18) 0.97(3) no . .
