#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237843.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237843
loop_
_publ_author_name
'González, María'
'Martínez, Andrea'
'Rivadulla, Marcos L.'
'Matos, Maria J.'
_publ_section_title
;
 [(2S,3aR,6aR)-5-Oxohexahydrofuro[3,2-b]furan-2-yl]methyl
 acetate
;
_journal_coeditor_code           GO2086
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o772
_journal_paper_doi               10.1107/S1600536813010313
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C9 H12 O5'
_chemical_formula_moiety         'C9 H12 O5'
_chemical_formula_sum            'C9 H12 O5'
_chemical_formula_weight         200.19
_chemical_melting_point          360.15(4)
_chemical_name_systematic
'[(2S,3aR,6aR)-5-Oxohexahydrofuro[3,2-b]furan-2-yl]methyl acetate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.755(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.015(5)
_cell_length_b                   4.647(3)
_cell_length_c                   10.904(5)
_cell_measurement_reflns_used    1040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.39
_cell_volume                     477.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2551
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.1292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1313
_reflns_number_total             1530
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            go2086.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2237843
_cod_database_fobs_code          2237843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.3092(3) 0.6053(7) 0.9619(3) 0.0455(7) Uani d . 1 1
H H1 0.3648 0.4273 0.9825 0.055 Uiso calc R 1 1
O O2 0.38327(19) 0.8441(5) 1.04241(19) 0.0546(6) Uani d . 1 1
C C3 0.3280(3) 0.9021(7) 1.1363(3) 0.0518(8) Uani d . 1 1
O O3 0.3786(3) 1.0867(6) 1.2155(2) 0.0788(7) Uani d . 1 1
C C4 0.2033(3) 0.7134(8) 1.1221(2) 0.0522(8) Uani d . 1 1
H H4A 0.1233 0.8252 1.1265 0.063 Uiso calc R 1 1
H H4B 0.2263 0.5674 1.1896 0.063 Uiso calc R 1 1
O O6 0.07106(19) 0.7479(6) 0.89421(18) 0.0656(7) Uani d . 1 1
C C5 0.1713(3) 0.5796(7) 0.9901(3) 0.0459(7) Uani d . 1 1
H H5 0.1407 0.3790 0.9887 0.055 Uiso calc R 1 1
C C7 0.1203(3) 0.8206(7) 0.7894(3) 0.0452(7) Uani d . 1 1
H H7 0.1309 1.0299 0.7865 0.054 Uiso calc R 1 1
C C8 0.2656(3) 0.6782(8) 0.8200(3) 0.0530(8) Uani d . 1 1
H H8A 0.2589 0.5060 0.7679 0.064 Uiso calc R 1 1
H H8B 0.3329 0.8095 0.8034 0.064 Uiso calc R 1 1
C C1' 0.0167(3) 0.7196(8) 0.6629(3) 0.0487(7) Uani d . 1 1
H H1A 0.0550 0.7489 0.5932 0.058 Uiso calc R 1 1
H H1B -0.0025 0.5161 0.6677 0.058 Uiso calc R 1 1
O O2' -0.1124(2) 0.8846(5) 0.63829(18) 0.0533(5) Uani d . 1 1
C C3' -0.2165(3) 0.8315(7) 0.5261(3) 0.0504(7) Uani d . 1 1
O O3' -0.2036(3) 0.6670(6) 0.4477(2) 0.0807(8) Uani d . 1 1
C C4' -0.3452(3) 1.0036(8) 0.5127(3) 0.0659(10) Uani d . 1 1
H H4E -0.3893 0.9331 0.5725 0.099 Uiso calc R 1 1
H H4D -0.4104 0.9876 0.4252 0.099 Uiso calc R 1 1
H H4C -0.3192 1.2017 0.5318 0.099 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0348(13) 0.0492(18) 0.0516(16) 0.0035(14) 0.0136(12) 0.0035(14)
O2 0.0410(10) 0.0622(14) 0.0599(12) -0.0120(11) 0.0162(9) -0.0041(11)
C3 0.0467(17) 0.057(2) 0.0405(16) 0.0046(16) 0.0004(13) 0.0065(15)
O3 0.0824(16) 0.0760(18) 0.0616(14) -0.0014(15) 0.0029(12) -0.0152(14)
C4 0.0471(16) 0.067(2) 0.0430(15) 0.0067(15) 0.0164(12) 0.0106(14)
O6 0.0410(11) 0.116(2) 0.0426(11) 0.0232(12) 0.0172(9) 0.0155(12)
C5 0.0432(15) 0.0489(17) 0.0472(15) -0.0005(14) 0.0173(12) 0.0039(14)
C7 0.0463(15) 0.0496(19) 0.0414(14) -0.0019(14) 0.0173(12) -0.0020(14)
C8 0.0455(16) 0.067(2) 0.0514(17) 0.0022(15) 0.0227(13) -0.0015(15)
C1' 0.0545(17) 0.0462(16) 0.0460(15) 0.0030(15) 0.0179(13) -0.0009(14)
O2' 0.0481(11) 0.0631(14) 0.0418(11) 0.0103(11) 0.0062(9) -0.0075(10)
C3' 0.0558(17) 0.0529(19) 0.0402(16) -0.0051(15) 0.0131(14) 0.0017(15)
O3' 0.0845(17) 0.088(2) 0.0559(13) 0.0072(14) 0.0055(12) -0.0251(15)
C4' 0.0491(18) 0.084(3) 0.054(2) 0.0063(16) 0.0039(15) 0.0061(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 C8 111.3(2)
O2 C1 C5 104.6(2)
C8 C1 C5 105.0(2)
O2 C1 H1 111.8
C8 C1 H1 111.8
C5 C1 H1 111.8
C3 O2 C1 110.8(2)
O3 C3 O2 120.5(3)
O3 C3 C4 129.1(3)
O2 C3 C4 110.4(3)
C3 C4 C5 104.1(2)
C3 C4 H4A 110.9
C5 C4 H4A 110.9
C3 C4 H4B 110.9
C5 C4 H4B 110.9
H4A C4 H4B 109.0
C5 O6 C7 111.7(2)
O6 C5 C4 110.4(3)
O6 C5 C1 105.9(2)
C4 C5 C1 104.3(2)
O6 C5 H5 111.9
C4 C5 H5 111.9
C1 C5 H5 111.9
O6 C7 C1' 110.1(2)
O6 C7 C8 106.5(2)
C1' C7 C8 112.2(2)
O6 C7 H7 109.3
C1' C7 H7 109.3
C8 C7 H7 109.3
C1 C8 C7 104.3(2)
C1 C8 H8A 110.9
C7 C8 H8A 110.9
C1 C8 H8B 110.9
C7 C8 H8B 110.9
H8A C8 H8B 108.9
O2' C1' C7 107.6(2)
O2' C1' H1A 110.2
C7 C1' H1A 110.2
O2' C1' H1B 110.2
C7 C1' H1B 110.2
H1A C1' H1B 108.5
C3' O2' C1' 116.4(2)
O3' C3' O2' 122.5(3)
O3' C3' C4' 125.4(3)
O2' C3' C4' 112.0(3)
C3' C4' H4E 109.5
C3' C4' H4D 109.5
H4E C4' H4D 109.5
C3' C4' H4C 109.5
H4E C4' H4C 109.5
H4D C4' H4C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.453(3)
C1 C8 1.498(4)
C1 C5 1.518(4)
C1 H1 0.9800
O2 C3 1.345(4)
C3 O3 1.201(4)
C3 C4 1.490(4)
C4 C5 1.500(4)
C4 H4A 0.9700
C4 H4B 0.9700
O6 C5 1.415(3)
O6 C7 1.430(3)
C5 H5 0.9800
C7 C1' 1.494(4)
C7 C8 1.530(4)
C7 H7 0.9800
C8 H8A 0.9700
C8 H8B 0.9700
C1' O2' 1.448(3)
C1' H1A 0.9700
C1' H1B 0.9700
O2' C3' 1.335(3)
C3' O3' 1.186(4)
C3' C4' 1.481(4)
C4' H4E 0.9600
C4' H4D 0.9600
C4' H4C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 C1 O2 C3 130.1(2)
C5 C1 O2 C3 17.2(3)
C1 O2 C3 O3 177.4(3)
C1 O2 C3 C4 -3.3(3)
O3 C3 C4 C5 167.1(3)
O2 C3 C4 C5 -12.1(3)
C7 O6 C5 C4 126.7(3)
C7 O6 C5 C1 14.4(3)
C3 C4 C5 O6 -91.7(3)
C3 C4 C5 C1 21.6(3)
O2 C1 C5 O6 92.8(3)
C8 C1 C5 O6 -24.5(3)
O2 C1 C5 C4 -23.7(3)
C8 C1 C5 C4 -141.0(3)
C5 O6 C7 C1' 123.3(3)
C5 O6 C7 C8 1.4(4)
O2 C1 C8 C7 -87.8(3)
C5 C1 C8 C7 24.8(3)
O6 C7 C8 C1 -16.7(3)
C1' C7 C8 C1 -137.3(3)
O6 C7 C1' O2' 66.4(3)
C8 C7 C1' O2' -175.2(2)
C7 C1' O2' C3' 177.6(2)
C1' O2' C3' O3' -2.9(4)
C1' O2' C3' C4' 178.0(3)
