#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021020.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_4021020
loop_
_publ_author_name
'Catherine Gaulon'
'Robert Dhal'
'Teddy Chapin'
'Vincent Maisonneuve'
'Gilles Dujardin'
_publ_section_title
;
 N-Vinyl-2-oxazolidinones: Efficient Chiral Dienophiles
 for the [4 + 2]-Based de Novo Synthesis of New N-2-Deoxyglycosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4192
_journal_page_last               4202
_journal_paper_doi               10.1021/jo040102y
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C16 H19 N O5'
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   '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                   7.5579(14)
_cell_length_b                   9.8711(12)
_cell_length_c                   21.1313(17)
_cell_measurement_temperature    293(2)
_cell_volume                     1576.5(4)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.286
_cod_database_code               4021020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4141(4) 0.5499(2) 0.16277(13) 0.0675(8) Uani 1 d . . .
O2 O 0.5797(4) 0.7033(2) 0.21354(12) 0.0590(7) Uani 1 d . . .
O3 O 0.3122(4) 0.9650(3) 0.09153(14) 0.0666(8) Uani 1 d . . .
O4 O 0.6814(4) 1.0362(3) 0.03267(12) 0.0633(8) Uani 1 d . . .
O5 O 0.5607(3) 1.2418(3) 0.04380(11) 0.0565(7) Uani 1 d . . .
N1 N 0.3855(4) 0.7633(3) 0.13242(13) 0.0457(7) Uani 1 d . . .
C1 C -0.0811(7) 0.6568(5) 0.0805(2) 0.0867(15) Uani 1 d . . .
H1A H -0.0712 0.6943 0.0387 0.081(3) Uiso 1 calc R . .
H1B H -0.1949 0.6789 0.0978 0.081(3) Uiso 1 calc R . .
H1C H -0.0683 0.5601 0.0784 0.081(3) Uiso 1 calc R . .
C2 C 0.0632(5) 0.7155(4) 0.12248(18) 0.0604(10) Uani 1 d . . .
H2A H 0.0445 0.8123 0.1269 0.081(3) Uiso 1 calc R . .
H2B H 0.0546 0.6753 0.1642 0.081(3) Uiso 1 calc R . .
C3 C 0.2464(5) 0.6909(4) 0.09642(16) 0.0463(9) Uani 1 d . . .
H3 H 0.2514 0.7161 0.0516 0.081(3) Uiso 1 calc R . .
C4 C 0.3102(6) 0.5458(4) 0.1054(2) 0.0692(12) Uani 1 d . . .
H4A H 0.2110 0.4842 0.1098 0.081(3) Uiso 1 calc R . .
H4B H 0.3819 0.5170 0.0698 0.081(3) Uiso 1 calc R . .
C5 C 0.4726(5) 0.6769(4) 0.17397(18) 0.0483(9) Uani 1 d . . .
C6 C 0.4137(5) 0.9020(3) 0.12486(16) 0.0470(8) Uani 1 d . . .
C7 C 0.5685(5) 0.9671(3) 0.15765(16) 0.0478(9) Uani 1 d . . .
H7A H 0.6752 0.9164 0.1483 0.081(3) Uiso 1 calc R . .
H7B H 0.5498 0.9648 0.2031 0.081(3) Uiso 1 calc R . .
C8 C 0.5917(5) 1.1134(3) 0.13624(15) 0.0408(8) Uani 1 d . . .
H8 H 0.4842 1.1635 0.1475 0.081(3) Uiso 1 calc R . .
C9 C 0.7488(4) 1.1851(3) 0.16628(15) 0.0397(8) Uani 1 d . . .
C10 C 0.9172(5) 1.1277(3) 0.16759(16) 0.0482(9) Uani 1 d . . .
H10 H 0.9336 1.0404 0.1522 0.081(3) Uiso 1 calc R . .
C11 C 0.9403(6) 0.6980(4) 0.30874(18) 0.0576(10) Uani 1 d . . .
H11 H 0.8289 0.6581 0.3082 0.081(3) Uiso 1 calc R . .
C12 C 0.9627(6) 0.8277(5) 0.28585(18) 0.0635(12) Uani 1 d . . .
H12 H 0.8669 0.8752 0.2694 0.081(3) Uiso 1 calc R . .
C13 C 0.8725(6) 1.3860(4) 0.2125(2) 0.0691(13) Uani 1 d . . .
H13 H 0.8571 1.4741 0.2272 0.081(3) Uiso 1 calc R . .
C14 C 0.7303(5) 1.3150(4) 0.18930(17) 0.0539(10) Uani 1 d . . .
H14 H 0.6192 1.3554 0.1891 0.081(3) Uiso 1 calc R . .
C15 C 0.6157(5) 1.1223(4) 0.06546(17) 0.0436(8) Uani 1 d . . .
C16 C 0.5838(6) 1.2676(5) -0.02352(17) 0.0725(12) Uani 1 d . . .
H16A H 0.7059 1.2557 -0.0347 0.081(3) Uiso 1 calc R . .
H16B H 0.5482 1.3587 -0.0329 0.081(3) Uiso 1 calc R . .
H16C H 0.5124 1.2054 -0.0473 0.081(3) Uiso 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 C5 1.350(4) . ?
O1 C4 1.445(4) . ?
O2 C5 1.193(4) . ?
O3 C6 1.213(4) . ?
O4 C15 1.204(4) . ?
O5 C15 1.332(4) . ?
O5 C16 1.456(4) . ?
N1 C5 1.390(4) . ?
N1 C6 1.395(4) . ?
N1 C3 1.481(4) . ?
C1 C2 1.521(6) . ?
C2 C3 1.510(5) . ?
C3 C4 1.523(5) . ?
C6 C7 1.503(5) . ?
C7 C8 1.523(4) . ?
C8 C15 1.509(5) . ?
C8 C9 1.521(5) . ?
C9 C14 1.379(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.375(5) 3_755 ?
C11 C10 1.375(5) 3_745 ?
C11 C12 1.378(6) . ?
C12 C13 1.373(6) 3_745 ?
C13 C12 1.373(6) 3_755 ?
C13 C14 1.374(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11278149
