#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021040.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_4021040
loop_
_publ_author_name
'Roland Messer'
'Andrea Schmitz'
'Luzia Moesch'
'Robert Häner'
_publ_section_title
;
 Elaboration of D-(-)-Ribose into a Tricyclic, Natural Product-like Scaffold
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8558
_journal_page_last               8560
_journal_paper_doi               10.1021/jo048351+
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C12 H14 O7'
_chemical_formula_weight         270.23
_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                 91.698(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6752(9)
_cell_length_b                   10.3589(10)
_cell_length_c                   8.7090(11)
_cell_measurement_temperature    153(2)
_cell_volume                     601.94(13)
_diffrn_ambient_temperature      153(2)
_exptl_crystal_density_diffrn    1.491
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021040
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 0.35653(17) 0.40939(11) 0.12054(13) 0.0245(3) Uani 1 1 d . . .
O2 O 0.65837(15) 0.43488(10) 0.00710(12) 0.0209(3) Uani 1 1 d . . .
O3 O 0.94525(17) 0.22783(14) 0.15201(14) 0.0316(3) Uani 1 1 d . . .
O4 O 0.9451(2) 0.23697(15) 0.40705(14) 0.0395(3) Uani 1 1 d . . .
O5 O 0.78624(18) 0.34095(11) -0.21325(13) 0.0257(3) Uani 1 1 d . . .
O6 O 0.3149(2) 0.42564(12) -0.19978(15) 0.0361(3) Uani 1 1 d . . .
O7 O 0.34532(18) 0.21244(11) -0.16574(13) 0.0256(3) Uani 1 1 d . . .
C1 C 0.3941(3) 0.40745(17) 0.27878(19) 0.0247(4) Uani 1 1 d . . .
C2 C 0.5192(3) 0.32568(18) 0.34620(19) 0.0253(4) Uani 1 1 d . . .
H2 H 0.533(3) 0.3228(19) 0.460(2) 0.023(4) Uiso 1 1 d . . .
C3 C 0.6274(2) 0.22270(16) 0.26192(18) 0.0230(3) Uani 1 1 d . . .
H3 H 0.591(3) 0.139(2) 0.302(2) 0.022(4) Uiso 1 1 d . . .
C4 C 0.8529(3) 0.23092(17) 0.28749(19) 0.0261(4) Uani 1 1 d . . .
C5 C 0.8046(3) 0.22953(18) 0.02315(19) 0.0251(4) Uani 1 1 d . . .
H5 H 0.832(3) 0.160(2) -0.0450(19) 0.020(4) Uiso 1 1 d . . .
C6 C 0.5918(2) 0.22321(16) 0.08754(17) 0.0214(3) Uani 1 1 d . . .
H6 H 0.515(3) 0.150(2) 0.0500(18) 0.017(4) Uiso 1 1 d . . .
C7 C 0.4943(2) 0.34800(14) 0.02741(19) 0.0199(3) Uani 1 1 d . . .
C8 C 0.8158(2) 0.36064(16) -0.05585(19) 0.0228(4) Uani 1 1 d . . .
H8 H 0.942(3) 0.4053(19) -0.0347(19) 0.023(5) Uiso 1 1 d . . .
C9 C 0.2689(3) 0.5050(2) 0.3560(2) 0.0346(4) Uani 1 1 d . . .
H9A H 0.128(5) 0.492(3) 0.326(3) 0.062(8) Uiso 1 1 d . . .
H9B H 0.298(3) 0.594(3) 0.318(3) 0.044(6) Uiso 1 1 d . . .
H9C H 0.285(4) 0.495(2) 0.471(3) 0.049(6) Uiso 1 1 d . . .
C10 C 0.8171(3) 0.45493(19) -0.3017(2) 0.0302(4) Uani 1 1 d . . .
H10A H 0.819(4) 0.433(2) -0.409(3) 0.049(6) Uiso 1 1 d . . .
H10B H 0.723(4) 0.517(3) -0.279(3) 0.073(9) Uiso 1 1 d . . .
H10C H 0.947(5) 0.486(3) -0.273(3) 0.062(7) Uiso 1 1 d . . .
C11 C 0.3747(2) 0.33424(18) -0.12715(19) 0.0226(4) Uani 1 1 d . . .
C12 C 0.2311(3) 0.18905(19) -0.3076(2) 0.0298(4) Uani 1 1 d . . .
H12A H 0.090(4) 0.213(3) -0.298(3) 0.050(6) Uiso 1 1 d . . .
H12B H 0.288(4) 0.234(3) -0.390(3) 0.052(7) Uiso 1 1 d . . .
H12C H 0.234(3) 0.098(3) -0.321(3) 0.040(6) 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
O1 C1 1.394(2) . ?
O1 C7 1.397(2) . ?
O2 C8 1.4250(19) . ?
O2 C7 1.4326(18) . ?
O3 C4 1.348(2) . ?
O3 C5 1.442(2) . ?
O4 C4 1.195(2) . ?
O5 C8 1.394(2) . ?
O5 C10 1.428(2) . ?
O6 C11 1.200(2) . ?
O7 C11 1.319(2) . ?
O7 C12 1.453(2) . ?
C1 C2 1.316(3) . ?
C1 C9 1.485(3) . ?
C2 C3 1.493(2) . ?
C3 C4 1.517(2) . ?
C3 C6 1.530(2) . ?
C5 C8 1.525(2) . ?
C5 C6 1.544(2) . ?
C6 C7 1.532(2) . ?
C7 C11 1.551(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21176615
2 PubChem 139089668
