#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020811.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_4020811
loop_
_publ_author_name
'James E. Tarver, Jr.'
'Madeleine M. Joullié'
_publ_section_title
;
 Synthesis of γ,δ-Unsaturated and γ,ε-Unsaturated
 α-Amino Acids from Fragmentation of γ- and δ-Lactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              815
_journal_page_last               820
_journal_paper_doi               10.1021/jo035401m
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C13 H23 N O5'
_chemical_formula_weight         273.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.278(3)
_cell_angle_beta                 102.391(4)
_cell_angle_gamma                99.080(4)
_cell_formula_units_Z            2
_cell_length_a                   6.3899(16)
_cell_length_b                   9.466(2)
_cell_length_c                   13.630(4)
_cell_measurement_temperature    143(1)
_cell_volume                     775.6(3)
_diffrn_ambient_temperature      143(1)
_exptl_crystal_density_diffrn    1.170
_cod_database_code               4020811
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
C1 C 0.6640(2) 0.25680(14) 0.33724(10) 0.0252(3) Uani 1 1 d . . .
H1A H 0.6010 0.1644 0.2863 0.033 Uiso 1 1 calc R . .
C2 C 0.8383(2) 0.23073(14) 0.42480(10) 0.0249(3) Uani 1 1 d . . .
H2A H 0.9495 0.3211 0.4541 0.033 Uiso 1 1 calc R . .
C3 C 0.7074(2) 0.20214(14) 0.50359(10) 0.0264(3) Uani 1 1 d . . .
H3A H 0.6399 0.0976 0.4867 0.035 Uiso 1 1 calc R . .
C4 C 0.5277(2) 0.28731(15) 0.48168(11) 0.0322(3) Uani 1 1 d . . .
C5 C 0.7382(2) 0.37715(15) 0.28243(10) 0.0280(3) Uani 1 1 d . . .
C6 C 0.5457(3) 0.3938(2) 0.19997(14) 0.0485(4) Uani 1 1 d . . .
H6A H 0.4329 0.4207 0.2316 0.073 Uiso 1 1 calc R . .
H6B H 0.4890 0.3025 0.1505 0.073 Uiso 1 1 calc R . .
H6C H 0.5941 0.4687 0.1660 0.073 Uiso 1 1 calc R . .
C7 C 0.9256(3) 0.34500(17) 0.23622(12) 0.0378(4) Uani 1 1 d . . .
H7A H 0.9641 0.4192 0.1999 0.057 Uiso 1 1 calc R . .
H7B H 0.8818 0.2509 0.1893 0.057 Uiso 1 1 calc R . .
H7C H 1.0497 0.3445 0.2902 0.057 Uiso 1 1 calc R . .
C8 C 0.9501(3) 0.10520(17) 0.39368(12) 0.0364(4) Uani 1 1 d . . .
H8A H 0.8417 0.0167 0.3639 0.055 Uiso 1 1 calc R . .
H8B H 1.0497 0.0921 0.4534 0.055 Uiso 1 1 calc R . .
H8C H 1.0292 0.1277 0.3441 0.055 Uiso 1 1 calc R . .
C9 C 0.7712(2) 0.17251(15) 0.68003(10) 0.0286(3) Uani 1 1 d . . .
C10 C 0.8710(3) 0.19180(17) 0.86648(11) 0.0362(4) Uani 1 1 d . . .
C11 C 0.8884(4) 0.0326(2) 0.86067(14) 0.0565(5) Uani 1 1 d . . .
H11A H 0.7753 -0.0288 0.8042 0.085 Uiso 1 1 calc R . .
H11B H 0.8719 0.0059 0.9237 0.085 Uiso 1 1 calc R . .
H11C H 1.0289 0.0200 0.8504 0.085 Uiso 1 1 calc R . .
C12 C 1.0612(3) 0.2911(2) 0.95002(12) 0.0506(5) Uani 1 1 d . . .
H12A H 1.1969 0.2723 0.9367 0.076 Uiso 1 1 calc R . .
H12B H 1.0516 0.2718 1.0159 0.076 Uiso 1 1 calc R . .
H12C H 1.0549 0.3918 0.9501 0.076 Uiso 1 1 calc R . .
C13 C 0.6535(4) 0.2205(3) 0.88232(15) 0.0668(6) Uani 1 1 d . . .
H13A H 0.6495 0.3219 0.8842 0.100 Uiso 1 1 calc R . .
H13B H 0.6350 0.1978 0.9462 0.100 Uiso 1 1 calc R . .
H13C H 0.5376 0.1600 0.8267 0.100 Uiso 1 1 calc R . .
N1 N 0.8330(2) 0.23985(13) 0.60882(9) 0.0326(3) Uani 1 1 d . . .
H1 H 0.9502 0.3069 0.6267 0.043 Uiso 1 1 calc R . .
O1 O 0.49440(16) 0.30486(11) 0.38429(8) 0.0323(3) Uani 1 1 d . . .
O2 O 0.4217(2) 0.33313(13) 0.53862(10) 0.0504(3) Uani 1 1 d . . .
O3 O 0.82337(16) 0.51202(10) 0.35676(8) 0.0329(3) Uani 1 1 d . . .
H3 H 0.7253 0.5377 0.3812 0.049 Uiso 1 1 calc R . .
O4 O 0.62020(18) 0.06904(11) 0.66324(7) 0.0352(3) Uani 1 1 d . . .
O5 O 0.90891(18) 0.23669(11) 0.77355(7) 0.0368(3) Uani 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
C1 O1 1.4638(16) . ?
C1 C2 1.5321(18) . ?
C1 C5 1.5380(18) . ?
C2 C8 1.5230(19) . ?
C2 C3 1.5313(18) . ?
C3 N1 1.4359(17) . ?
C3 C4 1.512(2) . ?
C4 O2 1.2031(18) . ?
C4 O1 1.3429(18) . ?
C5 O3 1.4266(17) . ?
C5 C7 1.515(2) . ?
C5 C6 1.527(2) . ?
C9 O4 1.2124(17) . ?
C9 N1 1.3453(18) . ?
C9 O5 1.3571(17) . ?
C10 O5 1.4611(17) . ?
C10 C13 1.510(3) . ?
C10 C11 1.518(2) . ?
C10 C12 1.523(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089601
