#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/07/4020778.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_4020778
loop_
_publ_author_name
'F. Christopher Pigge'
'John J. Coniglio'
'Nigam P. Rath'
_publ_section_title
;
 Functionalized Spiro- and Fused-Ring Heterocycles via
 Oxidative Demetalation of Cyclohexadienyl Ruthenium Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1161
_journal_page_last               1168
_journal_paper_doi               10.1021/jo035058l
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_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                 110.754(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0063(2)
_cell_length_b                   7.1259(1)
_cell_length_c                   11.4408(2)
_cell_measurement_temperature    200(2)
_cell_volume                     686.60(2)
_diffrn_ambient_temperature      200(2)
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020778
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_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
O1 O 0.27832(14) 0.3863(2) 0.36738(12) 0.0318(3) Uani 1 1 d . . .
O2 O 0.32960(15) 0.1502(2) 0.55960(12) 0.0361(3) Uani 1 1 d . . .
O3 O -0.30498(15) 0.1149(2) -0.07798(11) 0.0380(3) Uani 1 1 d . . .
O4 O -0.40215(16) 0.0562(2) 0.25939(13) 0.0409(4) Uani 1 1 d . . .
N1 N -0.10017(18) 0.2976(2) 0.03719(13) 0.0293(3) Uani 1 1 d . . .
C1 C 0.01890(19) 0.2562(3) 0.26308(15) 0.0254(3) Uani 1 1 d . . .
C2 C 0.16023(19) 0.2613(3) 0.36480(16) 0.0259(3) Uani 1 1 d . . .
C3 C 0.18798(19) 0.1325(3) 0.46288(15) 0.0279(3) Uani 1 1 d . . .
C4 C 0.0727(2) -0.0020(3) 0.45565(16) 0.0303(4) Uani 1 1 d . . .
H4 H 0.0910 -0.0918 0.5206 0.036 Uiso 1 1 calc R . .
C5 C -0.0696(2) -0.0054(3) 0.35319(17) 0.0293(4) Uani 1 1 d . . .
H5 H -0.1471 -0.0980 0.3493 0.035 Uiso 1 1 calc R . .
C6 C -0.09984(18) 0.1243(3) 0.25679(15) 0.0260(3) Uani 1 1 d . . .
C7 C -0.0118(2) 0.3904(3) 0.15565(15) 0.0291(4) Uani 1 1 d . . .
H7A H -0.0733 0.4991 0.1676 0.035 Uiso 1 1 calc R . .
H7B H 0.0906 0.4374 0.1533 0.035 Uiso 1 1 calc R . .
C8 C -0.0629(2) 0.3543(3) -0.07141(16) 0.0344(4) Uani 1 1 d . . .
H8A H -0.1289 0.2832 -0.1447 0.052 Uiso 1 1 calc R . .
H8B H 0.0495 0.3292 -0.0561 0.052 Uiso 1 1 calc R . .
H8C H -0.0840 0.4887 -0.0865 0.052 Uiso 1 1 calc R . .
C9 C -0.2236(2) 0.1804(3) 0.02475(16) 0.0285(4) Uani 1 1 d . . .
C10 C -0.24695(19) 0.1316(3) 0.14417(15) 0.0274(3) Uani 1 1 d . . .
C11 C -0.3946(2) 0.1031(3) 0.14640(17) 0.0311(4) Uani 1 1 d . . .
C12 C -0.5476(2) 0.1319(4) 0.03975(19) 0.0407(5) Uani 1 1 d . . .
H12A H -0.5252 0.1649 -0.0355 0.061 Uiso 1 1 calc R . .
H12B H -0.6075 0.2336 0.0601 0.061 Uiso 1 1 calc R . .
H12C H -0.6101 0.0160 0.0248 0.061 Uiso 1 1 calc R . .
C13 C -0.5521(2) 0.0193(4) 0.2729(2) 0.0472(6) Uani 1 1 d . . .
H13A H -0.5346 -0.0122 0.3602 0.071 Uiso 1 1 calc R . .
H13B H -0.6044 -0.0861 0.2190 0.071 Uiso 1 1 calc R . .
H13C H -0.6196 0.1310 0.2487 0.071 Uiso 1 1 calc R . .
C14 C 0.2587(3) 0.5704(3) 0.40962(19) 0.0390(4) Uani 1 1 d . . .
H14A H 0.3468 0.6504 0.4088 0.059 Uiso 1 1 calc R . .
H14B H 0.2576 0.5630 0.4949 0.059 Uiso 1 1 calc R . .
H14C H 0.1581 0.6237 0.3541 0.059 Uiso 1 1 calc R . .
C15 C 0.3597(3) 0.0228(4) 0.66168(19) 0.0468(5) Uani 1 1 d . . .
H15A H 0.4643 0.0493 0.7246 0.070 Uiso 1 1 calc R . .
H15B H 0.3577 -0.1062 0.6314 0.070 Uiso 1 1 calc R . .
H15C H 0.2779 0.0378 0.6991 0.070 Uiso 1 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
O1 C2 1.380(2) . ?
O1 C14 1.430(3) . ?
O2 C3 1.3663(19) . ?
O2 C15 1.427(3) . ?
O3 C9 1.235(2) . ?
O4 C11 1.360(2) . ?
O4 C13 1.437(2) . ?
N1 C9 1.357(2) . ?
N1 C8 1.455(2) . ?
N1 C7 1.464(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.406(2) . ?
C1 C7 1.503(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.394(3) . ?
C4 C5 1.398(2) . ?
C5 C6 1.390(2) . ?
C6 C10 1.486(2) . ?
C9 C10 1.495(2) . ?
C10 C11 1.355(2) . ?
C11 C12 1.496(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21176779
2 PubChem 139089588
