 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2002-11-11 at 12:47:59
#  Using CIFtbx version 2.6.2 16 Jun 1998
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.2
#  Request file    : c:\wingx\files\archive.dat
#  CIF files read  : ljf091 dreduc gaussian sortav struct
 
 
data_ljf091
 
_audit_creation_date            2002-11-11T12:47:59-00:00
_audit_creation_method         'WinGX routine CIF_UPDATE'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.2
_audit_conform_dict_location    ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category        FO
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C13 H20 O6'
_chemical_formula_sum                   'C13 H20 O6'
_chemical_formula_weight                272.29
_chemical_compound_source               'synthesis as described'
_chemical_absolute_configuration        syn
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P 21 21 21'
_symmetry_space_group_name_Hall         'P 2ac 2ab'
_symmetry_Int_Tables_number             19
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
 
_cell_length_a                          6.04560(10)
_cell_length_b                          13.5891(3)
_cell_length_c                          16.3997(4)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1347.31(5)
_cell_formula_units_Z                   4
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           1791
_cell_measurement_theta_min             1
_cell_measurement_theta_max             27.485
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              needle
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.62
_exptl_crystal_size_mid                 0.18
_exptl_crystal_size_min                 0.13
_exptl_crystal_density_diffrn           1.342
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    584
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
0 1 -1 0.11
0 -1 1 0.019
0 -1 -1 0.123
0 1 1 0.064
-1 0 0 0.279
1 0 0 0.342
 
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.106
_exptl_absorpt_correction_type          gaussian
_exptl_absorpt_process_details
;
   P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
   (1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min         0.956
_exptl_absorpt_correction_T_max         0.989
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_orient_matrix_type              'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             -0.125542
_diffrn_orient_matrix_ub_12             0.221666E-1
_diffrn_orient_matrix_ub_13             -0.35199E-1
_diffrn_orient_matrix_ub_21             0.951976E-1
_diffrn_orient_matrix_ub_22             0.533496E-1
_diffrn_orient_matrix_ub_23             -0.230733E-1
_diffrn_orient_matrix_ub_31             0.503691E-1
_diffrn_orient_matrix_ub_32             -0.455819E-1
_diffrn_orient_matrix_ub_33             -0.441227E-1
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0348
_diffrn_reflns_av_unetI/netI            0.0221
_diffrn_reflns_number                   23107
_diffrn_reflns_limit_h_min              -7
_diffrn_reflns_limit_h_max              7
_diffrn_reflns_limit_k_min              -17
_diffrn_reflns_limit_k_max              17
_diffrn_reflns_limit_l_min              -21
_diffrn_reflns_limit_l_max              21
_diffrn_reflns_theta_min                1.95
_diffrn_reflns_theta_max                27.5
_diffrn_reflns_theta_full               27.5
_diffrn_measured_fraction_theta_full
                                        0.996
_diffrn_measured_fraction_theta_max
                                        0.996
_reflns_number_total                    1795
_reflns_number_gt                       1574
_reflns_threshold_expression            >2sigma(I)
_diffrn_reflns_reduction_process
;
 Data from the short-exposure scan sets 1 & 2 were filtered, using only those
 reflections with I/sig(I) > 20 (filter file gaussian_hkl.sortav)
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397

;
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 Friedel pairs were merged using MERG 4, because preliminary refinements
 indicated that the absolute configuration could not be determined from this
 data
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0333P)²+0.2668P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef              0.021(2)
_refine_ls_number_reflns                1795
_refine_ls_number_parameters            178
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0396
_refine_ls_R_factor_gt                  0.0302
_refine_ls_wR_factor_ref                0.0705
_refine_ls_wR_factor_gt                 0.0668
_refine_ls_goodness_of_fit_ref          1.034
_refine_ls_restrained_S_all             1.034
_refine_ls_shift/su_max                 0.007
_refine_ls_shift/su_mean                0.001
_refine_diff_density_max                0.211
_refine_diff_density_min                -0.155
_refine_diff_density_rms                0.033
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
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 0.4343(2) 0.00702(8) 0.08063(7) 0.0312(3) Uani 1 1 d . . .
O2 O 0.3486(3) 0.17115(8) 0.08515(7) 0.0323(3) Uani 1 1 d . . .
O3 O 0.1431(2) 0.17750(9) 0.19760(7) 0.0315(3) Uani 1 1 d . . .
O4 O 0.6757(2) -0.11692(9) 0.29878(8) 0.0349(3) Uani 1 1 d . . .
H4A H 0.7248 -0.1747 0.2997 0.052 Uiso 1 1 calc R . .
O5 O 0.3924(2) -0.27270(8) 0.21487(6) 0.0218(3) Uani 1 1 d . . .
O6 O 0.2445(2) -0.19645(8) 0.10287(6) 0.0260(3) Uani 1 1 d . . .
C1 C 0.3143(3) 0.02185(12) 0.15442(10) 0.0214(4) Uani 1 1 d . . .
C2 C 0.4594(3) 0.00215(11) 0.22907(10) 0.0242(4) Uani 1 1 d . . .
H2A H 0.5918 0.045 0.2272 0.029 Uiso 1 1 calc R . .
H2B H 0.3759 0.0179 0.2793 0.029 Uiso 1 1 calc R . .
C3 C 0.5306(3) -0.10537(12) 0.23072(10) 0.0225(4) Uani 1 1 d . . .
H3 H 0.6142 -0.1203 0.1796 0.027 Uiso 1 1 calc R . .
C4 C 0.3320(3) -0.17373(11) 0.23592(9) 0.0211(3) Uani 1 1 d . . .
H4 H 0.268 -0.172 0.2921 0.025 Uiso 1 1 calc R . .
C5 C 0.1539(3) -0.15044(12) 0.17344(10) 0.0233(4) Uani 1 1 d . . .
H5 H 0.0135 -0.1844 0.1891 0.028 Uiso 1 1 calc R . .
C6 C 0.1069(3) -0.04234(12) 0.15757(11) 0.0267(4) Uani 1 1 d . . .
H6A H 0.0083 -0.0173 0.2011 0.032 Uiso 1 1 calc R . .
H6B H 0.0271 -0.0362 0.1051 0.032 Uiso 1 1 calc R . .
C7 C 0.2544(3) 0.13082(12) 0.15082(10) 0.0246(4) Uani 1 1 d . . .
C8 C 0.4686(3) 0.09705(12) 0.03845(11) 0.0274(4) Uani 1 1 d . . .
C9 C 0.7103(4) 0.12317(16) 0.03807(16) 0.0496(6) Uani 1 1 d . . .
H9A H 0.7625 0.1305 0.0943 0.074 Uiso 1 1 calc R . .
H9B H 0.7316 0.1852 0.0087 0.074 Uiso 1 1 calc R . .
H9C H 0.7941 0.0708 0.011 0.074 Uiso 1 1 calc R . .
C10 C 0.3670(4) 0.09233(15) -0.04505(11) 0.0431(6) Uani 1 1 d . . .
H10A H 0.4378 0.0398 -0.0766 0.065 Uiso 1 1 calc R . .
H10B H 0.3886 0.1554 -0.0729 0.065 Uiso 1 1 calc R . .
H10C H 0.2084 0.0787 -0.0401 0.065 Uiso 1 1 calc R . .
C11 C 0.3380(3) -0.28737(12) 0.12955(10) 0.0226(4) Uani 1 1 d . . .
C12 C 0.1687(3) -0.36986(13) 0.12279(11) 0.0301(4) Uani 1 1 d . . .
H12A H 0.0404 -0.3545 0.157 0.045 Uiso 1 1 calc R . .
H12B H 0.2354 -0.4318 0.1411 0.045 Uiso 1 1 calc R . .
H12C H 0.1213 -0.3764 0.0659 0.045 Uiso 1 1 calc R . .
C13 C 0.5444(4) -0.30660(15) 0.08077(12) 0.0370(5) Uani 1 1 d . . .
H13A H 0.5052 -0.316 0.0233 0.055 Uiso 1 1 calc R . .
H13B H 0.6175 -0.366 0.1014 0.055 Uiso 1 1 calc R . .
H13C H 0.6449 -0.2503 0.0859 0.055 Uiso 1 1 calc R . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 1.421(2) . ?
O1 C1 1.425(2) . ?
O2 C7 1.336(2) . ?
O2 C8 1.458(2) . ?
O3 C7 1.201(2) . ?
O4 C3 1.428(2) . ?
O4 H4A 0.84 . ?
O5 C4 1.4357(19) . ?
O5 C11 1.4511(19) . ?
O6 C5 1.4251(19) . ?
O6 C11 1.4274(19) . ?
C1 C7 1.526(2) . ?
C1 C6 1.528(2) . ?
C1 C2 1.530(2) . ?
C2 C3 1.523(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.520(2) . ?
C3 H3 1 . ?
C4 C5 1.520(2) . ?
C4 H4 1 . ?
C5 C6 1.519(2) . ?
C5 H5 1 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C8 C10 1.502(3) . ?
C8 C9 1.503(3) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C13 1.505(3) . ?
C11 C12 1.522(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C8 O1 C1 111.47(12) . . ?
C7 O2 C8 110.63(13) . . ?
C3 O4 H4A 109.5 . . ?
C4 O5 C11 107.64(11) . . ?
C5 O6 C11 106.44(12) . . ?
O1 C1 C7 103.02(13) . . ?
O1 C1 C6 111.45(13) . . ?
C7 C1 C6 111.14(14) . . ?
O1 C1 C2 111.26(13) . . ?
C7 C1 C2 109.69(13) . . ?
C6 C1 C2 110.10(14) . . ?
C3 C2 C1 110.12(13) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
O4 C3 C2 107.02(13) . . ?
O4 C3 C4 111.96(13) . . ?
C2 C3 C4 111.36(14) . . ?
O4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
O5 C4 C5 102.30(12) . . ?
O5 C4 C3 110.99(14) . . ?
C5 C4 C3 113.23(13) . . ?
O5 C4 H4 110 . . ?
C5 C4 H4 110 . . ?
C3 C4 H4 110 . . ?
O6 C5 C6 110.92(14) . . ?
O6 C5 C4 100.59(13) . . ?
C6 C5 C4 116.71(14) . . ?
O6 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C5 C6 C1 113.86(14) . . ?
C5 C6 H6A 108.8 . . ?
C1 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O3 C7 O2 122.47(16) . . ?
O3 C7 C1 128.37(16) . . ?
O2 C7 C1 109.16(14) . . ?
O1 C8 O2 105.44(13) . . ?
O1 C8 C10 110.32(15) . . ?
O2 C8 C10 107.75(14) . . ?
O1 C8 C9 110.32(16) . . ?
O2 C8 C9 108.82(16) . . ?
C10 C8 C9 113.81(19) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 O5 105.44(12) . . ?
O6 C11 C13 108.40(14) . . ?
O5 C11 C13 110.40(15) . . ?
O6 C11 C12 110.42(15) . . ?
O5 C11 C12 108.89(13) . . ?
C13 C11 C12 113.02(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
 
