 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H14 O7'
_chemical_formula_weight          318.27
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pca2(1)
_symmetry_space_group_name_hall   'P 2c -2ac'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y, z'
 '-x+1/2, y, z+1/2'
 
_cell_length_a                    16.4355(3)
_cell_length_b                    13.0381(2)
_cell_length_c                    6.51490(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1396.06(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4106
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        tablet
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.514
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              664
_exptl_absorpt_coefficient_mu     0.120
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.9648
_exptl_absorpt_correction_T_max   0.9916
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             5768
_diffrn_reflns_av_R_equivalents   0.0662
_diffrn_reflns_av_sigmaI/netI     0.0445
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -7
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          25.03
_reflns_number_total              1347
_reflns_number_gt                 1249
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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 > 2σ(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.
;
 
_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)+(0.0814P)²+0.2927P] 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_coef        0.033(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns          1347
_refine_ls_number_parameters      218
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0394
_refine_ls_R_factor_gt            0.0353
_refine_ls_wR_factor_ref          0.0956
_refine_ls_wR_factor_gt           0.0920
_refine_ls_goodness_of_fit_ref    0.889
_refine_ls_restrained_S_all       0.889
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.13913(14) 0.13297(19) 0.5004(4) 0.0188(5) Uani 1 1 d . . .
C2 C 0.15166(14) 0.23855(19) 0.4832(4) 0.0203(6) Uani 1 1 d . . .
H2 H 0.1074 0.2852 0.4728 0.024 Uiso 1 1 calc R . .
C3 C 0.23156(14) 0.27209(19) 0.4819(5) 0.0209(6) Uani 1 1 d . . .
C4 C 0.29727(15) 0.20463(19) 0.4986(5) 0.0211(6) Uani 1 1 d . . .
H4 H 0.3514 0.2302 0.4973 0.025 Uiso 1 1 calc R . .
C5 C 0.28323(14) 0.10154(19) 0.5170(4) 0.0182(6) Uani 1 1 d . . .
C6 C 0.20269(14) 0.06238(18) 0.5211(4) 0.0178(5) Uani 1 1 d . . .
C7 C 0.18626(15) -0.04529(18) 0.5466(4) 0.0178(6) Uani 1 1 d . . .
C8 C 0.10066(15) -0.07426(18) 0.5465(4) 0.0200(6) Uani 1 1 d . . .
C9 C 0.04434(14) -0.00079(19) 0.5210(5) 0.0211(6) Uani 1 1 d . . .
H9 H -0.0111 -0.0216 0.5188 0.025 Uiso 1 1 calc R . .
C10 C 0.07507(14) -0.18322(18) 0.5721(5) 0.0203(6) Uani 1 1 d . . .
C11 C 0.10328(15) -0.23987(19) 0.7398(5) 0.0216(6) Uani 1 1 d . . .
H11 H 0.1399 -0.2095 0.8348 0.026 Uiso 1 1 calc R . .
C12 C 0.07772(16) -0.34091(19) 0.7681(5) 0.0233(6) Uani 1 1 d . . .
C13 C 0.02400(14) -0.38493(19) 0.6278(5) 0.0229(6) Uani 1 1 d . . .
C14 C -0.00378(16) -0.3292(2) 0.4623(5) 0.0230(6) Uani 1 1 d . . .
H14 H -0.0405 -0.3595 0.3675 0.028 Uiso 1 1 calc R . .
C15 C 0.02223(15) -0.2279(2) 0.4339(5) 0.0238(6) Uani 1 1 d . . .
H15 H 0.0034 -0.1897 0.3190 0.029 Uiso 1 1 calc R . .
C16 C 0.19048(18) 0.44813(19) 0.4544(7) 0.0396(9) Uani 1 1 d . . .
H16A H 0.2148 0.5165 0.4419 0.059 Uiso 1 1 calc R . .
H16B H 0.1577 0.4448 0.5799 0.059 Uiso 1 1 calc R . .
H16C H 0.1558 0.4347 0.3351 0.059 Uiso 1 1 calc R . .
O1 O 0.25387(12) 0.37233(12) 0.4637(4) 0.0287(5) Uani 1 1 d . . .
O2 O 0.34735(10) 0.03609(14) 0.5321(3) 0.0225(5) Uani 1 1 d . . .
H2A H 0.3301 -0.0243 0.5432 0.034 Uiso 1 1 calc R . .
O1W O 0.19681(13) 0.69745(15) 0.2062(4) 0.0342(5) Uani 1 1 d D . .
O3 O 0.24266(11) -0.10982(12) 0.5674(3) 0.0232(5) Uani 1 1 d . . .
O4 O 0.06011(10) 0.10097(13) 0.4980(3) 0.0209(4) Uani 1 1 d . . .
O5 O 0.00134(13) -0.48420(14) 0.6667(4) 0.0292(5) Uani 1 1 d . . .
H5 H -0.0325 -0.5033 0.5781 0.044 Uiso 1 1 calc R . .
O6 O 0.10316(12) -0.40050(16) 0.9284(4) 0.0309(5) Uani 1 1 d . . .
H6 H 0.1338 -0.3660 1.0052 0.046 Uiso 1 1 calc R . .
H1W H 0.236(3) 0.719(3) 0.140(9) 0.103 Uiso 1 1 d D . .
H2W H 0.166(2) 0.721(3) 0.295(6) 0.060 Uiso 1 1 d D . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O4 1.364(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 O1 1.363(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 O2 1.360(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.439(3) . ?
C7 O3 1.259(3) . ?
C7 C8 1.457(3) . ?
C8 C9 1.342(3) . ?
C8 C10 1.491(3) . ?
C9 O4 1.360(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.380(4) . ?
C10 C11 1.398(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 O6 1.367(4) . ?
C12 C13 1.394(4) . ?
C13 O5 1.370(3) . ?
C13 C14 1.378(4) . ?
C14 C15 1.401(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.437(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O2 H2A 0.8400 . ?
O1W H1W 0.825(18) . ?
O1W H2W 0.828(18) . ?
O5 H5 0.8400 . ?
O6 H6 0.8400 . ?
 
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
O4 C1 C2 116.2(2) . . ?
O4 C1 C6 120.7(2) . . ?
C2 C1 C6 123.1(2) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
O1 C3 C2 124.0(2) . . ?
O1 C3 C4 113.7(2) . . ?
C2 C3 C4 122.3(2) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O2 C5 C4 119.5(2) . . ?
O2 C5 C6 119.7(2) . . ?
C4 C5 C6 120.8(2) . . ?
C1 C6 C5 117.3(2) . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 121.9(2) . . ?
O3 C7 C6 121.7(2) . . ?
O3 C7 C8 122.5(2) . . ?
C6 C7 C8 115.7(2) . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 C10 120.0(2) . . ?
C7 C8 C10 121.3(2) . . ?
C8 C9 O4 125.3(2) . . ?
C8 C9 H9 117.3 . . ?
O4 C9 H9 117.3 . . ?
C15 C10 C11 119.7(2) . . ?
C15 C10 C8 120.4(3) . . ?
C11 C10 C8 119.8(2) . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O6 C12 C13 117.4(2) . . ?
O6 C12 C11 123.0(3) . . ?
C13 C12 C11 119.5(3) . . ?
O5 C13 C14 123.5(2) . . ?
O5 C13 C12 116.1(3) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 O1 C16 117.9(2) . . ?
C5 O2 H2A 109.5 . . ?
H1W O1W H2W 135(4) . . ?
C9 O4 C1 118.59(18) . . ?
C13 O5 H5 109.5 . . ?
C12 O6 H6 109.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O5 H5 O6  0.84 1.97 2.761(3) 157.1 2_544
O6 H6 O1W  0.84 1.86 2.697(3) 171.5 1_546
O1W H1W O3  0.825(18) 2.31(4) 2.850(3) 124(4) 4_564
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.232
_refine_diff_density_min   -0.288
_refine_diff_density_rms    0.058
