##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
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data_global
_audit_creation_method     CRYSTALS_ver_12.86
_journal_date_recd_electronic     2009-01-20
_journal_date_accepted     2009-01-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     o414
_journal_page_last     o415
_journal_paper_category     QO
_journal_coeditor_code     LH2760
_publ_contact_author_name     'Sarah Jenkinson'
_publ_contact_author_address
;
Department of Organic Chemistry
Chemistry Research Laboratory
Department of Chemistry
University of Oxford
Oxford OX1 3TA
England
;
_publ_contact_author_email     sarah.jenkinson@chem.ox.ac.uk
_publ_contact_author_fax     '+44 1865 000000'
_publ_contact_author_phone     '+44 1865 275655'
_publ_section_title
;
(1S)-1,2-O-Benzylidene-α-D-glucurono-6,3-lactone
;
loop_
    _publ_author_name
    _publ_author_address
    'Jenkinson, Sarah F.'
;
Department of Organic Chemistry
Chemistry Research Laboratory
Department of Chemistry
University of Oxford
Oxford OX1 3TA
England
;
    'Best, Daniel'
;
Department of Organic Chemistry
Chemistry Research Laboratory
Department of Chemistry
University of Oxford
Oxford OX1 3TA
England
;
    'Weymouth-Wilson, Alexander C.'
;
Dextra Laboratories Ltd
Science and Technology Centre
Whiteknights Road
Reading RG6 6BZ
England
;
    'Clarkson, Robert A.'
;
Dextra Laboratories Ltd
Science and Technology Centre
Whiteknights Road
Reading RG6 6BZ
England
;
    'Fleet, George W. J.'
;
Department of Organic Chemistry
Chemistry Research Laboratory
Department of Chemistry
University of Oxford
Oxford OX1 3TA
England
;
    'Watkin, David J.'
;
Department of Chemical Crystallography
Chemistry Research Laboratory
Department of Chemistry
University of Oxford
Oxford OX1 3TA
England
;
_chemical_name_systematic     ?
_chemical_melting_point     ?
data_I
_chemical_name_systematic
;
(1S)-1,2-O-Benzylidene-α-D-glucurono-6,3-lactone
;
_chemical_formula_moiety     'C13 H12 O6'
_chemical_formula_sum     'C13 H12 O6'
_chemical_formula_iupac     'C13 H12 O6'
_chemical_formula_weight     264.23
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,y+1/2,-z'
_cell_length_a     5.63290(10)
_cell_length_b     7.8943(2)
_cell_length_c     13.3182(3)
_cell_angle_alpha     90
_cell_angle_beta     99.9545(9)
_cell_angle_gamma     90
_cell_volume     583.32(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1368
_cell_measurement_theta_min     5
_cell_measurement_theta_max     27
_cell_measurement_temperature     150
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.504
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     276
_exptl_absorpt_coefficient_mu     0.121
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.88
_exptl_absorpt_correction_T_max     0.96
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_device     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     ω
_diffrn_reflns_number     8275
_diffrn_reflns_av_R_equivalents     0.022
_diffrn_reflns_theta_min     5.208
_diffrn_reflns_theta_max     27.498
_diffrn_reflns_theta_full     26.123
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     1418
_reflns_number_gt     1341
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0291
_refine_ls_R_factor_gt     0.0271
_refine_ls_wR_factor_all     0.0676
_refine_ls_wR_factor_gt     0.0664
_refine_ls_wR_factor_ref     0.0676
_refine_ls_goodness_of_fit_ref     0.9573
_refine_ls_number_reflns     1418
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method = modified Sheldrick
w = 1/[σ²(F²) + (0.04P)² + 0.13P],
where P = [max(Fo²,0) + 2Fc²]/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.009181
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.18
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2001)'
_computing_cell_refinement     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al.,  1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al.,  2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.1555(2) 0.28908(18) 1.09521(9) 0.0317 Uani 1.0000 . .
    C C2 1.0013(3) 0.2487(3) 1.02461(12) 0.0257 Uani 1.0000 . .
    O O3 1.04981(19) 0.2312(2) 0.92986(9) 0.0296 Uani 1.0000 . .
    C C4 0.8321(3) 0.1868(2) 0.85789(12) 0.0263 Uani 1.0000 . .
    C C5 0.6246(3) 0.2272(2) 0.91452(12) 0.0246 Uani 1.0000 . .
    C C6 0.7382(3) 0.2089(2) 1.02587(12) 0.0259 Uani 1.0000 . .
    O O7 0.6540(2) 0.3147(2) 1.09703(9) 0.0334 Uani 1.0000 . .
    O O8 0.5720(2) 0.40215(18) 0.89088(9) 0.0285 Uani 1.0000 . .
    C C9 0.6089(3) 0.4347(2) 0.79011(12) 0.0265 Uani 1.0000 . .
    C C10 0.8011(3) 0.3081(2) 0.76761(12) 0.0267 Uani 1.0000 . .
    O O11 0.6942(2) 0.2266(2) 0.67619(9) 0.0323 Uani 1.0000 . .
    C C12 0.4413(3) 0.2413(2) 0.66815(12) 0.0269 Uani 1.0000 . .
    O O13 0.4052(2) 0.40025(19) 0.71549(9) 0.0307 Uani 1.0000 . .
    C C14 0.3210(3) 0.2382(2) 0.55862(12) 0.0266 Uani 1.0000 . .
    C C15 0.1004(3) 0.1573(3) 0.53152(14) 0.0320 Uani 1.0000 . .
    C C16 -0.0149(3) 0.1563(3) 0.43042(15) 0.0379 Uani 1.0000 . .
    C C17 0.0921(3) 0.2338(3) 0.35636(14) 0.0374 Uani 1.0000 . .
    C C18 0.3143(3) 0.3125(3) 0.38315(14) 0.0368 Uani 1.0000 . .
    C C19 0.4288(3) 0.3166(3) 0.48437(14) 0.0321 Uani 1.0000 . .
    H H41 0.8338 0.0667 0.8363 0.0325 Uiso 1.0000 . .
    H H51 0.4805 0.1554 0.8912 0.0314 Uiso 1.0000 . .
    H H61 0.7293 0.0846 1.0439 0.0312 Uiso 1.0000 . .
    H H91 0.6542 0.5570 0.7843 0.0323 Uiso 1.0000 . .
    H H101 0.9551 0.3623 0.7612 0.0324 Uiso 1.0000 . .
    H H121 0.3793 0.1500 0.7071 0.0326 Uiso 1.0000 . .
    H H151 0.0235 0.1040 0.5830 0.0404 Uiso 1.0000 . .
    H H161 -0.1724 0.1016 0.4108 0.0448 Uiso 1.0000 . .
    H H171 0.0114 0.2344 0.2852 0.0453 Uiso 1.0000 . .
    H H181 0.3876 0.3631 0.3302 0.0450 Uiso 1.0000 . .
    H H191 0.5853 0.3725 0.5058 0.0382 Uiso 1.0000 . .
    H H71 0.5030 0.2905 1.0901 0.0522 Uiso 1.0000 . .
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
    O1 0.0237(6) 0.0355(8) 0.0344(6) 0.0018(5) 0.0009(5) -0.0001(5)
    C2 0.0234(7) 0.0216(7) 0.0319(8) 0.0030(7) 0.0044(6) 0.0031(7)
    O3 0.0193(5) 0.0384(7) 0.0316(6) 0.0026(5) 0.0051(4) 0.0001(6)
    C4 0.0213(7) 0.0265(8) 0.0306(8) 0.0011(6) 0.0036(6) -0.0021(7)
    C5 0.0209(7) 0.0227(8) 0.0306(8) -0.0016(7) 0.0058(6) -0.0001(7)
    C6 0.0233(7) 0.0256(9) 0.0295(8) -0.0013(7) 0.0059(6) 0.0014(7)
    O7 0.0262(6) 0.0428(8) 0.0325(6) -0.0009(6) 0.0088(5) -0.0056(6)
    O8 0.0309(6) 0.0268(6) 0.0286(6) 0.0060(6) 0.0077(5) 0.0009(5)
    C9 0.0291(8) 0.0228(8) 0.0276(8) 0.0000(7) 0.0050(6) -0.0006(6)
    C10 0.0226(7) 0.0295(9) 0.0286(8) -0.0018(7) 0.0064(6) -0.0018(7)
    O11 0.0252(5) 0.0416(7) 0.0302(6) 0.0068(6) 0.0047(4) -0.0076(6)
    C12 0.0251(7) 0.0240(8) 0.0319(8) 0.0009(7) 0.0061(6) -0.0012(7)
    O13 0.0285(6) 0.0316(7) 0.0305(6) 0.0082(6) 0.0010(5) -0.0051(5)
    C14 0.0267(7) 0.0231(8) 0.0302(8) 0.0019(7) 0.0056(6) -0.0024(7)
    C15 0.0291(8) 0.0301(9) 0.0380(9) -0.0033(8) 0.0095(7) -0.0071(8)
    C16 0.0298(9) 0.0393(11) 0.0432(11) -0.0038(8) 0.0021(8) -0.0154(9)
    C17 0.0419(10) 0.0367(10) 0.0319(8) 0.0061(9) 0.0014(7) -0.0079(9)
    C18 0.0423(10) 0.0343(10) 0.0344(9) 0.0016(9) 0.0083(8) 0.0017(8)
    C19 0.0314(8) 0.0291(9) 0.0363(9) -0.0040(8) 0.0068(7) 0.0011(8)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 . . 1.207(2) no
    C2 O3 . . 1.344(2) no
    C2 C6 . . 1.518(2) no
    O3 C4 . . 1.4628(19) no
    C4 C5 . . 1.530(2) no
    C4 C10 . . 1.524(2) no
    C4 H41 . . 0.991 no
    C5 C6 . . 1.517(2) no
    C5 O8 . . 1.436(2) no
    C5 H51 . . 0.995 no
    C6 O7 . . 1.406(2) no
    C6 H61 . . 1.014 no
    O7 H71 . . 0.861 no
    O8 C9 . . 1.417(2) no
    C9 C10 . . 1.540(2) no
    C9 O13 . . 1.4088(19) no
    C9 H91 . . 1.005 no
    C10 O11 . . 1.416(2) no
    C10 H101 . . 0.984 no
    O11 C12 . . 1.4148(19) no
    C12 O13 . . 1.435(2) no
    C12 C14 . . 1.499(2) no
    C12 H121 . . 0.987 no
    C14 C15 . . 1.388(2) no
    C14 C19 . . 1.392(3) no
    C15 C16 . . 1.390(3) no
    C15 H151 . . 0.969 no
    C16 C17 . . 1.384(3) no
    C16 H161 . . 0.981 no
    C17 C18 . . 1.388(3) no
    C17 H171 . . 0.977 no
    C18 C19 . . 1.390(3) no
    C18 H181 . . 0.963 no
    C19 H191 . . 0.983 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C2 O3 . . . 121.52(15) no
    O1 C2 C6 . . . 128.19(15) no
    O3 C2 C6 . . . 110.28(13) no
    C2 O3 C4 . . . 110.88(12) no
    O3 C4 C5 . . . 104.62(13) no
    O3 C4 C10 . . . 109.58(14) no
    C5 C4 C10 . . . 105.37(13) no
    O3 C4 H41 . . . 111.7 no
    C5 C4 H41 . . . 112.9 no
    C10 C4 H41 . . . 112.2 no
    C4 C5 C6 . . . 103.48(12) no
    C4 C5 O8 . . . 103.80(13) no
    C6 C5 O8 . . . 109.98(14) no
    C4 C5 H51 . . . 112.3 no
    C6 C5 H51 . . . 115.8 no
    O8 C5 H51 . . . 110.7 no
    C2 C6 C5 . . . 102.55(12) no
    C2 C6 O7 . . . 109.20(14) no
    C5 C6 O7 . . . 117.93(14) no
    C2 C6 H61 . . . 106.9 no
    C5 C6 H61 . . . 107.1 no
    O7 C6 H61 . . . 112.2 no
    C6 O7 H71 . . . 103.8 no
    C5 O8 C9 . . . 108.88(13) no
    O8 C9 C10 . . . 106.84(14) no
    O8 C9 O13 . . . 113.45(14) no
    C10 C9 O13 . . . 104.58(13) no
    O8 C9 H91 . . . 109.2 no
    C10 C9 H91 . . . 114.3 no
    O13 C9 H91 . . . 108.5 no
    C9 C10 C4 . . . 104.06(13) no
    C9 C10 O11 . . . 104.69(13) no
    C4 C10 O11 . . . 111.49(15) no
    C9 C10 H101 . . . 113.3 no
    C4 C10 H101 . . . 111.0 no
    O11 C10 H101 . . . 111.9 no
    C10 O11 C12 . . . 107.49(12) no
    O11 C12 O13 . . . 104.83(13) no
    O11 C12 C14 . . . 110.64(13) no
    O13 C12 C14 . . . 111.54(15) no
    O11 C12 H121 . . . 110.1 no
    O13 C12 H121 . . . 108.5 no
    C14 C12 H121 . . . 111.0 no
    C12 O13 C9 . . . 108.59(12) no
    C12 C14 C15 . . . 119.63(16) no
    C12 C14 C19 . . . 120.33(15) no
    C15 C14 C19 . . . 120.04(16) no
    C14 C15 C16 . . . 120.10(18) no
    C14 C15 H151 . . . 120.4 no
    C16 C15 H151 . . . 119.5 no
    C15 C16 C17 . . . 119.99(17) no
    C15 C16 H161 . . . 120.7 no
    C17 C16 H161 . . . 119.3 no
    C16 C17 C18 . . . 119.95(17) no
    C16 C17 H171 . . . 120.4 no
    C18 C17 H171 . . . 119.6 no
    C17 C18 C19 . . . 120.40(18) no
    C17 C18 H181 . . . 118.6 no
    C19 C18 H181 . . . 121.0 no
    C14 C19 C18 . . . 119.51(17) no
    C14 C19 H191 . . . 118.2 no
    C18 C19 H191 . . . 122.3 no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C4 H41 O1 . . 2_747 0.99 2.37 3.200(3) 141 no
    C6 H61 O8 . . 2_647 1.01 2.49 3.289(3) 135 no
    C9 H91 O1 . . 2_757 1.01 2.55 3.349(3) 137 no
    C15 H151 O11 . . 1_455 0.97 2.59 3.281(3) 128 no
    C16 H161 O13 . . 2_546 0.98 2.51 3.350(3) 143 no
    O7 H71 O1 . . 1_455 0.86 1.97 2.811(3) 165 yes
