data_01sot198
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Daniel Price
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H10 O8'
_chemical_formula_weight          330.24
 
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'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.1662(7)
_cell_length_b                    14.3524(14)
_cell_length_c                    12.0930(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.590(4)
_cell_angle_gamma                 90.00
_cell_volume                      1335.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     19752
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.643
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              680
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9787
_exptl_absorpt_correction_T_max   0.9933
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             16495
_diffrn_reflns_av_R_equivalents   0.1215
_diffrn_reflns_av_sigmaI/netI     0.1218
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.65
_diffrn_reflns_theta_max          27.42
_reflns_number_total              2965
_reflns_number_gt                 1309
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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.
;
 
_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)+(0.0991P)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     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2965
_refine_ls_number_parameters      221
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1848
_refine_ls_R_factor_gt            0.0669
_refine_ls_wR_factor_ref          0.2034
_refine_ls_wR_factor_gt           0.1468
_refine_ls_goodness_of_fit_ref    0.983
_refine_ls_restrained_S_all       0.983
_refine_ls_shift/su_max           0.001
_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 0.4196(4) 0.1490(2) -0.1141(3) 0.0247(8) Uani 1 1 d . . .
H1 H 0.3206 0.1694 -0.1768 0.030 Uiso 1 1 calc R . .
C2 C 0.4148(4) 0.1477(2) -0.0007(3) 0.0225(8) Uani 1 1 d . . .
C3 C 0.5567(4) 0.1156(2) 0.0915(3) 0.0256(9) Uani 1 1 d . . .
H3 H 0.5523 0.1137 0.1690 0.031 Uiso 1 1 calc R . .
C4 C 0.7057(5) 0.0863(2) 0.0694(3) 0.0236(8) Uani 1 1 d . . .
C5 C 0.7114(4) 0.0897(2) -0.0435(3) 0.0247(8) Uani 1 1 d . . .
H5 H 0.8142 0.0708 -0.0575 0.030 Uiso 1 1 calc R . .
C6 C 0.5689(4) 0.1206(2) -0.1372(3) 0.0229(8) Uani 1 1 d . . .
C7 C 0.2595(5) 0.1863(3) 0.0207(3) 0.0275(9) Uani 1 1 d . . .
C8 C 0.8621(5) 0.0583(3) 0.1682(3) 0.0288(9) Uani 1 1 d . . .
C9 C 0.5735(4) 0.1246(2) -0.2592(3) 0.0248(8) Uani 1 1 d . . .
C10 C 0.7212(4) 0.1547(2) -0.2815(3) 0.0249(8) Uani 1 1 d . . .
H10 H 0.8221 0.1720 -0.2183 0.030 Uiso 1 1 calc R . .
C11 C 0.7215(4) 0.1596(2) -0.3965(3) 0.0236(8) Uani 1 1 d . . .
C12 C 0.5777(4) 0.1337(2) -0.4889(3) 0.0245(8) Uani 1 1 d . . .
H12 H 0.5794 0.1366 -0.5670 0.029 Uiso 1 1 calc R . .
C13 C 0.4296(4) 0.1033(2) -0.4674(3) 0.0228(8) Uani 1 1 d . . .
C14 C 0.4275(4) 0.0992(2) -0.3531(3) 0.0240(8) Uani 1 1 d . . .
H14 H 0.3256 0.0790 -0.3390 0.029 Uiso 1 1 calc R . .
C15 C 0.8779(5) 0.1969(2) -0.4183(3) 0.0261(9) Uani 1 1 d . . .
C16 C 0.2728(5) 0.0756(2) -0.5654(3) 0.0282(9) Uani 1 1 d . . .
O1 O 0.1336(3) 0.21616(18) -0.0592(2) 0.0359(7) Uani 1 1 d . . .
O2 O 0.2709(3) 0.18813(19) 0.13099(19) 0.0347(7) Uani 1 1 d . . .
H2 H 0.1804 0.2121 0.1370 0.052 Uiso 1 1 calc R . .
O3 O 0.8420(3) 0.05449(19) 0.2698(2) 0.0378(7) Uani 1 1 d . . .
H3A H 0.9389 0.0457 0.3220 0.057 Uiso 1 1 calc R . .
O4 O 1.0026(3) 0.04366(18) 0.1520(2) 0.0363(7) Uani 1 1 d . . .
O5 O 1.0046(3) 0.22595(19) -0.3384(2) 0.0401(7) Uani 1 1 d . . .
O6 O 0.8667(3) 0.19811(18) -0.5281(2) 0.0333(7) Uani 1 1 d . . .
H6 H 0.9598 0.2188 -0.5338 0.050 Uiso 1 1 calc R . .
O7 O 0.2891(3) 0.07684(19) -0.6680(2) 0.0368(7) Uani 1 1 d . . .
H7 H 0.1918 0.0674 -0.7195 0.055 Uiso 1 1 calc R . .
O8 O 0.1352(3) 0.05385(18) -0.5479(2) 0.0346(7) Uani 1 1 d . . .
 
 
_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 C2 1.385(5) . ?
C1 C6 1.400(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(4) . ?
C2 C7 1.484(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 C8 1.483(5) . ?
C5 C6 1.397(4) . ?
C5 H5 0.9500 . ?
C6 C9 1.489(5) . ?
C7 O1 1.228(4) . ?
C7 O2 1.305(4) . ?
C8 O4 1.245(4) . ?
C8 O3 1.294(4) . ?
C9 C10 1.391(5) . ?
C9 C14 1.392(5) . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(5) . ?
C11 C15 1.488(5) . ?
C12 C13 1.390(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(5) . ?
C13 C16 1.478(5) . ?
C14 H14 0.9500 . ?
C15 O5 1.228(4) . ?
C15 O6 1.300(4) . ?
C16 O8 1.251(4) . ?
C16 O7 1.291(4) . ?
O2 H2 0.8400 . ?
O3 H3A 0.8400 . ?
O6 H6 0.8400 . ?
O7 H7 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
C2 C1 C6 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 C7 118.5(3) . . ?
C3 C2 C7 121.0(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C8 120.0(3) . . ?
C3 C4 C8 119.9(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C9 121.7(3) . . ?
C1 C6 C9 119.9(3) . . ?
O1 C7 O2 123.4(3) . . ?
O1 C7 C2 122.1(3) . . ?
O2 C7 C2 114.4(3) . . ?
O4 C8 O3 124.0(3) . . ?
O4 C8 C4 120.6(3) . . ?
O3 C8 C4 115.3(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C6 121.1(3) . . ?
C14 C9 C6 120.0(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 C15 120.3(3) . . ?
C10 C11 C15 118.9(3) . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 C16 119.4(3) . . ?
C12 C13 C16 120.6(3) . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O5 C15 O6 123.4(3) . . ?
O5 C15 C11 122.0(3) . . ?
O6 C15 C11 114.5(3) . . ?
O8 C16 O7 123.6(3) . . ?
O8 C16 C13 121.1(3) . . ?
O7 C16 C13 115.2(3) . . ?
C7 O2 H2 109.5 . . ?
C8 O3 H3A 109.5 . . ?
C15 O6 H6 109.5 . . ?
C16 O7 H7 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
C6 C1 C2 C3 -1.8(5) . . . . ?
C6 C1 C2 C7 174.7(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C7 C2 C3 C4 -175.1(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 C8 175.7(3) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C8 C4 C5 C6 -176.6(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C9 180.0(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C6 C9 -178.5(3) . . . . ?
C1 C2 C7 O1 2.6(5) . . . . ?
C3 C2 C7 O1 179.0(3) . . . . ?
C1 C2 C7 O2 -175.6(3) . . . . ?
C3 C2 C7 O2 0.9(5) . . . . ?
C5 C4 C8 O4 4.8(5) . . . . ?
C3 C4 C8 O4 -170.6(3) . . . . ?
C5 C4 C8 O3 -177.9(3) . . . . ?
C3 C4 C8 O3 6.6(5) . . . . ?
C5 C6 C9 C10 -40.2(5) . . . . ?
C1 C6 C9 C10 139.1(3) . . . . ?
C5 C6 C9 C14 140.6(3) . . . . ?
C1 C6 C9 C14 -40.0(5) . . . . ?
C14 C9 C10 C11 0.3(5) . . . . ?
C6 C9 C10 C11 -178.8(3) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C9 C10 C11 C15 176.7(3) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C15 C11 C12 C13 -176.9(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C11 C12 C13 C16 179.7(3) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
C16 C13 C14 C9 179.8(3) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C6 C9 C14 C13 179.6(3) . . . . ?
C12 C11 C15 O5 175.5(3) . . . . ?
C10 C11 C15 O5 -2.1(5) . . . . ?
C12 C11 C15 O6 -2.9(5) . . . . ?
C10 C11 C15 O6 179.5(3) . . . . ?
C14 C13 C16 O8 4.3(5) . . . . ?
C12 C13 C16 O8 -175.3(3) . . . . ?
C14 C13 C16 O7 -176.5(3) . . . . ?
C12 C13 C16 O7 3.9(5) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.973
_diffrn_reflns_theta_full              27.42
_diffrn_measured_fraction_theta_full   0.973
_refine_diff_density_max    0.384
_refine_diff_density_min   -0.287
_refine_diff_density_rms    0.080
