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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL
_chemical_name_systematic
;
(1R,5R,8S)-8-benzyloxy-2,6-dioxabicyclo[3.2.1]octane-3-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H14 O4'
_chemical_formula_sum     'C13 H14 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C13 H14 O4'
_chemical_formula_weight     234.24
_chemical_melting_point     ?
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21'
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'
_cell_length_a     5.7290(10)
_cell_length_b     10.079(2)
_cell_length_c     19.622(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1133.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     5.2
_cell_measurement_theta_max     15.2
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'rectangular plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .45
_exptl_crystal_size_mid      .35
_exptl_crystal_size_min      .20
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu      .845
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min      .656
_exptl_absorpt_correction_T_max      .845
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device     'syntex P2₁'
_diffrn_measurement_method     θ/2θ
_diffrn_reflns_number     2583
_diffrn_reflns_av_R_equivalents      .056
_diffrn_reflns_av_sigmaI/netI      .051
_diffrn_reflns_theta_min     4.5
_diffrn_reflns_theta_max     80.1
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     2
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     15
_reflns_number_total     2259
_reflns_number_gt     1969
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     'Fsqd'
_refine_ls_matrix_type     'full'
_refine_ls_R_factor_all      .043
_refine_ls_R_factor_gt      .033
_refine_ls_wR_factor_all      .091
_refine_ls_wR_factor_ref      .088
_refine_ls_goodness_of_fit_all     1.09
_refine_ls_goodness_of_fit_ref     1.13
_refine_ls_restrained_S_all     1.09
_refine_ls_restrained_S_obs     1.13
_refine_ls_number_reflns     2259
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
                                'calc w = 1/[σ²(Fo²)+(0.0559P)²+0.0550P]'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .19
_refine_diff_density_min      -.26
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef      .0083(9)
_refine_ls_abs_structure_details     '(Flack, 1983). No Fridel pairs.'
_refine_ls_abs_structure_Flack      -.03(19)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0181  .0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0492  .0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'P2₁ Software (Syntex, 1973)'
_computing_cell_refinement     'P2₁ Software'
_computing_data_reduction     "XP21 (Pavelčík, 1993)"
_computing_structure_solution     'SHELXS86 (Sheldrick, 1985)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP (Johnson, 1965)'
_computing_publication_material     'SHELXL97'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1  -.4214(2)  .24478(18)  .29568(8)  .0445(4) Uani d . 1 . . C
    O2  -.4622(2)  .37260(14)  .32678(6)  .0538(3) Uani d . 1 . . O
    C3  -.2930(4)  .46570(19)  .32421(9)  .0529(4) Uani d . 1 . . C
    C4  -.0674(3)  .43483(18)  .28864(9)  .0473(4) Uani d . 1 . . C
    C5  -.0524(2)  .29627(16)  .26008(7)  .0376(3) Uani d . 1 . . C
    O6  -.02398(17)  .20177(11)  .31404(5)  .0428(3) Uani d . 1 . . O
    C7  -.2526(3)  .1624(2)  .33694(9)  .0475(4) Uani d . 1 . . C
    C8  -.2892(3)  .25985(17)  .22971(7)  .0391(3) Uani d . 1 . . C
    O9  -.3347(4)  .57093(18)  .35005(9)  .0915(6) Uani d . 1 . . O
    O10  -.38899(18)  .35580(12)  .18662(5)  .0432(3) Uani d . 1 . . O
    C11  -.2684(4)  .3619(3)  .12267(9)  .0634(6) Uani d . 1 . . C
    C12  -.4202(3)  .42940(19)  .07084(7)  .0439(4) Uani d . 1 . . C
    C13  -.3498(3)  .5472(2)  .04215(10)  .0553(4) Uani d . 1 . . C
    C14  -.4850(4)  .6068(3)  -.00776(11)  .0713(7) Uani d . 1 . . C
    C15  -.6913(4)  .5506(3)  -.02770(9)  .0698(6) Uani d . 1 . . C
    C16  -.7632(3)  .4337(3)  .00136(10)  .0634(6) Uani d . 1 . . C
    C17  -.6279(3)  .3725(2)  .05074(9)  .0521(4) Uani d . 1 . . C
    H1  -.056(4)  .490(2)  .2511(11)  .057 Uiso d . 1 . . H
    H2  -.280(3)  .175(2)  .2055(10)  .045 Uiso d . 1 . . H
    H3  -.263(3)  .180(2)  .3841(11)  .046 Uiso d . 1 . . H
    H4  -.692(5)  .285(3)  .0733(13)  .079 Uiso d . 1 . . H
    H5  -.222(5)  .268(3)  .1109(15)  .087 Uiso d . 1 . . H
    H6  -.793(6)  .592(3)  -.0682(17)  .120 Uiso d . 1 . . H
    H7  -.275(4)  .060(3)  .3251(11)  .061 Uiso d . 1 . . H
    H8  -.427(5)  .686(3)  -.0256(15)  .088 Uiso d . 1 . . H
    H9  .080(4)  .2857(19)  .2291(10)  .045 Uiso d . 1 . . H
    H10  .060(4)  .451(2)  .3212(11)  .058 Uiso d . 1 . . H
    H11  -.200(5)  .583(3)  .0566(14)  .088 Uiso d . 1 . . H
    H12  -.917(6)  .396(3)  -.0149(14)  .088 Uiso d . 1 . . H
    H13  -.568(4)  .210(2)  .2920(10)  .044 Uiso d . 1 . . H
    H15  -.102(8)  .412(3)  .1285(19)  .124 Uiso d . 1 . . H
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  .0329(6)  .0518(10)  .0488(8)  -.0036(7)  .0012(6)  .0074(7)
    O2  .0477(6)  .0656(8)  .0482(6)  .0152(6)  .0113(5)  .0008(5)
    C3  .0699(10)  .0454(11)  .0435(8)  .0187(9)  -.0059(7)  -.0023(7)
    C4  .0488(7)  .0423(9)  .0508(8)  -.0055(7)  -.0073(7)  .0074(7)
    C5  .0308(6)  .0416(9)  .0404(7)  .0042(6)  .0012(5)  .0078(6)
    O6  .0374(5)  .0433(6)  .0476(6)  .0040(4)  -.0043(4)  .0130(5)
    C7  .0455(8)  .0505(11)  .0464(8)  -.0043(7)  -.0001(6)  .0138(7)
    C8  .0389(6)  .0403(9)  .0379(6)  .0057(6)  -.0043(6)  .0010(6)
    O9  .1342(16)  .0565(10)  .0839(10)  .0363(11)  -.0030(12)  -.0191(8)
    O10  .0444(5)  .0518(7)  .0333(5)  .0145(5)  -.0019(4)  .0032(5)
    C11  .0558(10)  .0961(17)  .0383(8)  .0321(11)  .0035(7)  .0131(9)
    C12  .0442(7)  .0564(10)  .0312(6)  .0128(7)  .0018(5)  .0004(6)
    C13  .0473(8)  .0631(13)  .0557(9)  -.0015(8)  .0052(7)  .0044(8)
    C14  .0796(14)  .0718(16)  .0625(11)  .0141(11)  .0197(11)  .0297(11)
    C15  .0736(12)  .0996(18)  .0362(8)  .0353(13)  -.0060(8)  .0049(9)
    C16  .0541(10)  .0805(16)  .0555(10)  .0118(10)  -.0138(8)  -.0236(10)
    C17  .0527(9)  .0479(11)  .0557(9)  .0046(8)  .0042(7)  -.0069(8)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O2 . 1.445(2) y
    C1 C7 . 1.510(2) y
    C1 C8 . 1.507(2) y
    C1 H13 .  .91(2) ?
    O2 C3 . 1.350(3) y
    C3 C4 . 1.501(3) y
    C3 O9 . 1.200(2) y
    C4 C5 . 1.507(3) y
    C4 H1 .  .93(2) ?
    C4 H10 .  .99(2) ?
    C5 O6 . 1.4334(17) y
    C5 C8 . 1.527(2) y
    C5 H9 .  .98(2) ?
    O6 C7 . 1.4402(19) y
    C7 H3 .  .94(2) ?
    C7 H7 . 1.06(3) ?
    C8 O10 . 1.4060(17) y
    C8 H2 .  .98(2) ?
    O10 C11 . 1.4338(19) y
    C11 C12 . 1.501(2) y
    C11 H5 . 1.01(3) ?
    C11 H15 . 1.08(4) ?
    C12 C13 . 1.375(3) y
    C12 C17 . 1.378(3) y
    C13 C14 . 1.385(3) y
    C13 H11 .  .98(3) ?
    C14 C15 . 1.368(4) y
    C14 H8 .  .93(3) ?
    C15 C16 . 1.372(4) y
    C15 H6 . 1.07(4) ?
    C16 C17 . 1.386(3) y
    C16 H12 . 1.01(3) ?
    C17 H4 . 1.05(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 C1 C7 . . 111.55(14) y
    O2 C1 C8 . . 110.74(14) y
    C8 C1 C7 . . 101.19(12) y
    O2 C1 H13 . . 103.1(12) ?
    C8 C1 H13 . . 115.6(12) ?
    C7 C1 H13 . . 114.9(13) ?
    C3 O2 C1 . . 119.21(12) y
    O9 C3 O2 . . 117.1(2) y
    O9 C3 C4 . . 123.4(2) y
    O2 C3 C4 . . 119.43(15) y
    C3 C4 C5 . . 114.46(15) y
    C3 C4 H1 . . 107.7(14) ?
    C5 C4 H1 . . 104.9(13) ?
    C3 C4 H10 . . 107.7(12) ?
    C5 C4 H10 . . 110.6(13) ?
    H1 C4 H10 . . 111.4(19) ?
    O6 C5 C4 . . 110.34(12) y
    O6 C5 C8 . . 103.25(12) y
    C4 C5 C8 . . 108.49(13) y
    O6 C5 H9 . . 107.4(12) ?
    C4 C5 H9 . . 112.2(11) ?
    C8 C5 H9 . . 114.8(12) ?
    C5 O6 C7 . . 108.07(11) y
    O6 C7 C1 . . 105.31(12) y
    O6 C7 H3 . . 108.0(12) ?
    C1 C7 H3 . . 112.5(12) ?
    O6 C7 H7 . . 107.9(13) ?
    C1 C7 H7 . . 109.8(12) ?
    H3 C7 H7 . . 113.0(17) ?
    O10 C8 C1 . . 112.43(13) y
    O10 C8 C5 . . 115.50(13) y
    C1 C8 C5 . . 97.79(11) y
    O10 C8 H2 . . 109.2(12) ?
    C1 C8 H2 . . 110.9(12) ?
    C5 C8 H2 . . 110.6(12) ?
    C8 O10 C11 . . 111.11(12) y
    O10 C11 C12 . . 109.48(13) y
    O10 C11 H5 . . 106.7(17) ?
    C12 C11 H5 . . 114.9(17) ?
    O10 C11 H15 . . 111(2) ?
    C12 C11 H15 . . 112(2) ?
    H5 C11 H15 . . 103(3) ?
    C13 C12 C17 . . 119.68(16) y
    C13 C12 C11 . . 119.94(18) y
    C17 C12 C11 . . 120.37(19) y
    C12 C13 C14 . . 120.01(19) y
    C12 C13 H11 . . 117.5(17) ?
    C14 C13 H11 . . 122.4(17) ?
    C15 C14 C13 . . 120.4(2) y
    C15 C14 H8 . . 123.6(18) ?
    C13 C14 H8 . . 116.1(18) ?
    C14 C15 C16 . . 119.77(18) y
    C14 C15 H6 . . 122(2) ?
    C16 C15 H6 . . 118(2) ?
    C15 C16 C17 . . 120.3(2) y
    C15 C16 H12 . . 117.0(16) ?
    C17 C16 H12 . . 122.7(16) ?
    C12 C17 C16 . . 119.9(2) y
    C12 C17 H4 . . 121.9(15) ?
    C16 C17 H4 . . 118.1(15) ?
data_global
_journal_date_recd_electronic     2000-12-19
_journal_date_accepted     2001-03-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      4
_journal_page_first     o360
_journal_page_last     o361
_journal_paper_category     EO
_publ_contact_author
;
Marian Koman
Department of Inorganic Chemistry
Slovak Technical University
Radlinského 9
812 37 Bratislava
Slovak Republic
;
_publ_contact_author_email     koman@cvtstu.cvt.stuba.sk
_publ_contact_author_fax     '00421 7 52499257'
_publ_contact_author_phone     '00421 7 59325623'
_publ_section_title
;
Absolute configuration of the newly formed asymmetric centre in
(1R,5R,8S)-8-benzyloxy-2,6-dioxabicyclo[3.2.1]octane-3-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Koman, Marian'
;     Department of Inorganic Chemistry
      Slovak Technical University
      Radlinského 9
      812 37 Bratislava
      Slovakia
;
    'Babjak Matej'
;     Department of Organic Chemistry
      Slovak Technical University
      Radlinského 9
      812 37 Bratislava
      Slovakia
;
    'Gracza Tibor'
;     Department of Organic Chemistry
      Slovak Technical University
      Radlinského 9
      812 37 Bratislava
      Slovakia
;
    'Glowiak Tadeusz'
;     Faculty of Chemistry
      University Of Wroclaw
      14 F.Joliot-Curie street
      50-383 Wroclaw
      Poland
;
