#\#CIF_1.1
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2004-02-27 at 15:59:49
#  Using CIFtbx version 2.6.2 16 Jun 1998
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : c:\wingx\files\archive.dat
#  CIF files read  : ljf111 dreduc sortabs sortav struct
 
 
data_ljf111
 
_audit_creation_date                    2004-02-27T15:59:49-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C16 H22 O8, 0.2(O H2)'
_chemical_formula_sum                   'C16 H22.40 O8.20'
_chemical_formula_weight                345.94
_chemical_compound_source               'synthesis as described'
_chemical_absolute_configuration        syn
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 21'
_symmetry_space_group_name_Hall         'P 2yb'
_symmetry_Int_Tables_number             4
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
 
_cell_length_a                          10.3677(12)
_cell_length_b                          5.6294(5)
_cell_length_c                          16.1459(19)
_cell_angle_alpha                       90
_cell_angle_beta                        106.470(4)
_cell_angle_gamma                       90
_cell_volume                            903.67(17)
_cell_formula_units_Z                   2
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           1451
_cell_measurement_theta_min             2.19
_cell_measurement_theta_max             25.682
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              needle
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.7
_exptl_crystal_size_mid                 0.08
_exptl_crystal_size_min                 0.08
_exptl_crystal_density_diffrn           1.271
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    368
_exptl_special_details
;
 Crystals grow as multi-crystals as very long needles. A single specimen
 was cleaved from a large clump. As the crystals did not cleave well
 perpendicular to the needle direction, it was unavoidable to use a 
 specimen which was much longer than the X-ray beam cross-section
 (~ 0.5mm) for the diffraction data. 
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.103
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min         0.913
_exptl_absorpt_correction_T_max         1.041
 
#----------------------------------------------------------------------------#
#                   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             -0.883326E-1
_diffrn_orient_matrix_ub_12             -0.683426E-1
_diffrn_orient_matrix_ub_13             -0.33676E-1
_diffrn_orient_matrix_ub_21             0.420844E-1
_diffrn_orient_matrix_ub_22             -0.586978E-1
_diffrn_orient_matrix_ub_23             -0.447365E-1
_diffrn_orient_matrix_ub_31             0.232962E-1
_diffrn_orient_matrix_ub_32             -0.153099
_diffrn_orient_matrix_ub_33             0.321846E-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         0.0346
_diffrn_reflns_av_unetI/netI            0.065
_diffrn_reflns_number                   4909
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -5
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min              -19
_diffrn_reflns_limit_l_max              19
_diffrn_reflns_theta_min                2.63
_diffrn_reflns_theta_max                25.8
_diffrn_reflns_theta_full               25.8
_diffrn_measured_fraction_theta_full
                                        0.974
_diffrn_measured_fraction_theta_max
                                        0.974
_reflns_number_total                    3020
_reflns_number_gt                       2093
_reflns_threshold_expression            >2sigma(I)
_diffrn_reflns_reduction_process
;
 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.

 A single peak in the difference map at ~ 0.9 e/A-3 was assumed to be a
 partially occupied  water molecule at 20% occupancy. This atom is 2.67 /A
 from the hydroxyl oxygen atom O(19) and there are no other residuals 
 greater than  +/- 0.2 e/A-3. Hydrogen atoms for this putative water molecule
 were not included in the model.

 The absolute configuration was not determined through the diffraction data
 but from the synthetic route.
;
_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)+(0.0536P)²+0.0000P] 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            none
_refine_ls_number_reflns                3020
_refine_ls_number_parameters            226
_refine_ls_number_restraints            1
_refine_ls_R_factor_all                 0.0717
_refine_ls_R_factor_gt                  0.0465
_refine_ls_wR_factor_ref                0.1111
_refine_ls_wR_factor_gt                 0.0963
_refine_ls_goodness_of_fit_ref          1.056
_refine_ls_restrained_S_all             1.056
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          -1.2(13)
_refine_diff_density_max                0.167
_refine_diff_density_min                -0.162
_refine_diff_density_rms                0.038
 
#----------------------------------------------------------------------------#
#                   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
C C 0.0033 0.0016 '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'
O O 0.0106 0.006 '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
C1 C 0.0596(3) 0.3430(5) 0.38647(19) 0.0402(7) Uani 1 1 d . . .
C2 C -0.0198(3) 0.1209(5) 0.3795(2) 0.0457(8) Uani 1 1 d . . .
H2A H 0.0166 0.0262 0.4327 0.055 Uiso 1 1 calc R . .
H2B H -0.0081 0.0267 0.3304 0.055 Uiso 1 1 calc R . .
C3 C -0.1682(3) 0.1606(6) 0.3667(2) 0.0480(8) Uani 1 1 d . . .
H3 H -0.1823 0.2693 0.4123 0.058 Uiso 1 1 calc R . .
C5 C -0.3293(3) 0.3975(6) 0.2641(2) 0.0505(9) Uani 1 1 d . . .
C6 C -0.3613(3) 0.5112(7) 0.1792(2) 0.0537(8) Uani 1 1 d . . .
H6 H -0.4479 0.5798 0.1569 0.064 Uiso 1 1 calc R . .
C7 C -0.2764(3) 0.5237(5) 0.1319(2) 0.0452(8) Uani 1 1 d . . .
H7 H -0.1915 0.4488 0.1541 0.054 Uiso 1 1 calc R . .
C8 C -0.3021(3) 0.6433(6) 0.0481(2) 0.0510(9) Uani 1 1 d . . .
H8 H -0.28 0.5308 0.0062 0.061 Uiso 1 1 calc R . .
C9 C -0.2171(3) 0.8651(6) 0.05323(19) 0.0480(8) Uani 1 1 d . . .
H9 H -0.2501 0.9903 0.0862 0.058 Uiso 1 1 calc R . .
C11 C 0.0060(3) 0.9655(6) 0.1400(2) 0.0465(8) Uani 1 1 d . . .
C12 C 0.1352(3) 0.8728(5) 0.1944(2) 0.0438(8) Uani 1 1 d . . .
H12 H 0.2094 0.979 0.2104 0.053 Uiso 1 1 calc R . .
C13 C 0.1542(3) 0.6535(5) 0.2221(2) 0.0409(7) Uani 1 1 d . . .
H13 H 0.0809 0.5462 0.2034 0.049 Uiso 1 1 calc R . .
C14 C 0.2821(3) 0.5590(6) 0.2807(2) 0.0423(7) Uani 1 1 d . . .
H14 H 0.3075 0.4115 0.2545 0.051 Uiso 1 1 calc R . .
C15 C 0.2687(3) 0.4985(6) 0.3705(2) 0.0497(8) Uani 1 1 d . . .
H15 H 0.2389 0.6416 0.3969 0.06 Uiso 1 1 calc R . .
C17 C -0.2435(4) -0.0691(6) 0.3660(3) 0.0700(11) Uani 1 1 d . . .
H17A H -0.3397 -0.0355 0.3548 0.105 Uiso 1 1 calc R . .
H17B H -0.21 -0.1478 0.4221 0.105 Uiso 1 1 calc R . .
H17C H -0.2297 -0.1732 0.3206 0.105 Uiso 1 1 calc R . .
C20 C -0.2156(4) 0.9638(7) -0.0332(2) 0.0736(12) Uani 1 1 d . . .
H20A H -0.1554 1.1013 -0.0246 0.11 Uiso 1 1 calc R . .
H20B H -0.3068 1.0127 -0.0654 0.11 Uiso 1 1 calc R . .
H20C H -0.1838 0.8414 -0.0659 0.11 Uiso 1 1 calc R . .
C23 C 0.3957(3) 0.3974(9) 0.4310(2) 0.0794(13) Uani 1 1 d . . .
H23A H 0.3801 0.36 0.4866 0.119 Uiso 1 1 calc R . .
H23B H 0.4683 0.5143 0.4396 0.119 Uiso 1 1 calc R . .
H23C H 0.421 0.2524 0.4058 0.119 Uiso 1 1 calc R . .
O4 O -0.21387(18) 0.2734(3) 0.28224(13) 0.0468(5) Uani 1 1 d . . .
O10 O -0.08047(18) 0.7944(3) 0.10219(13) 0.0426(5) Uani 1 1 d . . .
O16 O 0.16673(18) 0.3118(3) 0.35680(13) 0.0451(5) Uani 1 1 d . . .
O18 O -0.39697(19) 0.4137(4) 0.31412(15) 0.0584(6) Uani 1 1 d . . .
O19 O -0.4395(2) 0.7163(5) 0.01426(15) 0.0760(8) Uani 1 1 d . . .
H19 H -0.4463 0.8099 -0.0273 0.114 Uiso 1 1 calc R . .
O21 O -0.0216(2) 1.1752(4) 0.13127(17) 0.0637(7) Uani 1 1 d . . .
O22 O 0.38641(19) 0.7304(4) 0.28937(17) 0.0613(7) Uani 1 1 d . . .
H22 H 0.4611 0.661 0.3006 0.092 Uiso 1 1 calc R . .
O24 O 0.0340(2) 0.5274(4) 0.41608(16) 0.0565(6) Uani 1 1 d . . .
O100 O -0.4731(10) 0.4755(19) -0.1332(7) 0.054(3) Uiso 0.2 1 d P . .
 
 
 
#----------------------------------------------------------------------------#
#                   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
C1 O24 1.203(3) . ?
C1 O16 1.340(3) . ?
C1 C2 1.483(4) . ?
C2 C3 1.510(4) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 O4 1.457(4) . ?
C3 C17 1.509(4) . ?
C3 H3 1 . ?
C5 O18 1.215(3) . ?
C5 O4 1.344(3) . ?
C5 C6 1.462(5) . ?
C6 C7 1.320(4) . ?
C6 H6 0.95 . ?
C7 C8 1.467(5) . ?
C7 H7 0.95 . ?
C8 O19 1.434(3) . ?
C8 C9 1.517(5) . ?
C8 H8 1 . ?
C9 O10 1.468(3) . ?
C9 C20 1.506(5) . ?
C9 H9 1 . ?
C11 O21 1.213(4) . ?
C11 O10 1.339(4) . ?
C11 C12 1.473(4) . ?
C12 C13 1.309(4) . ?
C12 H12 0.95 . ?
C13 C14 1.492(4) . ?
C13 H13 0.95 . ?
C14 O22 1.426(3) . ?
C14 C15 1.534(4) . ?
C14 H14 1 . ?
C15 O16 1.462(3) . ?
C15 C23 1.510(4) . ?
C15 H15 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
O19 H19 0.84 . ?
O22 H22 0.84 . ?
 
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
O24 C1 O16 123.6(3) . . ?
O24 C1 C2 125.3(2) . . ?
O16 C1 C2 111.1(2) . . ?
C1 C2 C3 114.1(2) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
O4 C3 C17 109.7(3) . . ?
O4 C3 C2 103.9(2) . . ?
C17 C3 C2 112.3(3) . . ?
O4 C3 H3 110.3 . . ?
C17 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
O18 C5 O4 122.7(3) . . ?
O18 C5 C6 124.7(3) . . ?
O4 C5 C6 112.5(2) . . ?
C7 C6 C5 123.6(3) . . ?
C7 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C6 C7 C8 125.6(3) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
O19 C8 C7 112.6(3) . . ?
O19 C8 C9 106.5(3) . . ?
C7 C8 C9 112.1(3) . . ?
O19 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
O10 C9 C20 109.7(2) . . ?
O10 C9 C8 105.3(2) . . ?
C20 C9 C8 114.3(3) . . ?
O10 C9 H9 109.1 . . ?
C20 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
O21 C11 O10 122.8(3) . . ?
O21 C11 C12 123.9(3) . . ?
O10 C11 C12 113.3(3) . . ?
C13 C12 C11 124.1(3) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 C13 C14 125.0(3) . . ?
C12 C13 H13 117.5 . . ?
C14 C13 H13 117.5 . . ?
O22 C14 C13 109.5(3) . . ?
O22 C14 C15 109.1(2) . . ?
C13 C14 C15 112.1(2) . . ?
O22 C14 H14 108.7 . . ?
C13 C14 H14 108.7 . . ?
C15 C14 H14 108.7 . . ?
O16 C15 C23 106.7(3) . . ?
O16 C15 C14 105.8(2) . . ?
C23 C15 C14 113.5(2) . . ?
O16 C15 H15 110.2 . . ?
C23 C15 H15 110.2 . . ?
C14 C15 H15 110.2 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 O4 C3 117.6(2) . . ?
C11 O10 C9 118.0(2) . . ?
C1 O16 C15 119.2(2) . . ?
C8 O19 H19 109.5 . . ?
C14 O22 H22 109.5 . . ?
 
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
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
O24 C1 C2 C3 31.0(5) . . . . ?
O16 C1 C2 C3 -150.2(3) . . . . ?
C1 C2 C3 O4 65.4(3) . . . . ?
C1 C2 C3 C17 -176.1(3) . . . . ?
O18 C5 C6 C7 168.5(3) . . . . ?
O4 C5 C6 C7 -10.5(5) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C6 C7 C8 O19 -9.5(5) . . . . ?
C6 C7 C8 C9 110.6(3) . . . . ?
O19 C8 C9 O10 170.0(2) . . . . ?
C7 C8 C9 O10 46.5(3) . . . . ?
O19 C8 C9 C20 -69.5(3) . . . . ?
C7 C8 C9 C20 166.9(2) . . . . ?
O21 C11 C12 C13 161.7(3) . . . . ?
O10 C11 C12 C13 -16.9(4) . . . . ?
C11 C12 C13 C14 -176.8(3) . . . . ?
C12 C13 C14 O22 -10.3(4) . . . . ?
C12 C13 C14 C15 110.9(3) . . . . ?
O22 C14 C15 O16 -176.4(2) . . . . ?
C13 C14 C15 O16 62.2(3) . . . . ?
O22 C14 C15 C23 -59.8(4) . . . . ?
C13 C14 C15 C23 178.8(3) . . . . ?
O18 C5 O4 C3 -1.7(4) . . . . ?
C6 C5 O4 C3 177.4(3) . . . . ?
C17 C3 O4 C5 80.4(3) . . . . ?
C2 C3 O4 C5 -159.4(2) . . . . ?
O21 C11 O10 C9 -4.4(4) . . . . ?
C12 C11 O10 C9 174.2(2) . . . . ?
C20 C9 O10 C11 77.3(3) . . . . ?
C8 C9 O10 C11 -159.3(2) . . . . ?
O24 C1 O16 C15 8.2(4) . . . . ?
C2 C1 O16 C15 -170.5(2) . . . . ?
C23 C15 O16 C1 113.8(3) . . . . ?
C14 C15 O16 C1 -125.1(3) . . . . ?
 
