data_02sot082
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Bataille
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H22 O6'
_chemical_formula_weight          286.32
 
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            Orthorhombic
_symmetry_space_group_name_H-M    Pna2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    9.3133(3)
_cell_length_b                    15.4441(4)
_cell_length_c                    9.8424(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1415.69(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     15124
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.343
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              616
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9733
_exptl_absorpt_correction_T_max   0.9896
_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             14735
_diffrn_reflns_av_R_equivalents   0.0585
_diffrn_reflns_av_sigmaI/netI     0.0433
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.29
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3218
_reflns_number_gt                 2831
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_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)+(0.0417P)²+0.1548P] 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        0.0098(16)
_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_abs_structure_Flack    0.7(7)
_refine_ls_number_reflns          3218
_refine_ls_number_parameters      186
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0435
_refine_ls_R_factor_gt            0.0340
_refine_ls_wR_factor_ref          0.0810
_refine_ls_wR_factor_gt           0.0767
_refine_ls_goodness_of_fit_ref    1.024
_refine_ls_restrained_S_all       1.024
_refine_ls_shift/su_max           0.014
_refine_ls_shift/su_mean          0.001
 
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 0.37380(15) -0.06606(9) 0.24155(16) 0.0188(3) Uani 1 1 d . . .
C2 C 0.50287(17) -0.09643(10) 0.31964(17) 0.0229(3) Uani 1 1 d . . .
H2A H 0.5879 -0.1011 0.2597 0.027 Uiso 1 1 calc R . .
H2B H 0.4847 -0.1534 0.3623 0.027 Uiso 1 1 calc R . .
C3 C 0.52451(16) -0.02669(9) 0.42679(16) 0.0208(3) Uani 1 1 d . . .
H3A H 0.6277 -0.0180 0.4465 0.025 Uiso 1 1 calc R . .
H3B H 0.4739 -0.0416 0.5121 0.025 Uiso 1 1 calc R . .
C4 C 0.45854(16) 0.05412(9) 0.35985(15) 0.0182(3) Uani 1 1 d . . .
C5 C 0.56890(17) 0.10534(10) 0.27875(17) 0.0236(3) Uani 1 1 d . . .
H5A H 0.6219 0.0660 0.2189 0.035 Uiso 1 1 calc R . .
H5B H 0.6360 0.1337 0.3412 0.035 Uiso 1 1 calc R . .
H5C H 0.5198 0.1493 0.2240 0.035 Uiso 1 1 calc R . .
C6 C 0.37830(15) 0.11338(9) 0.45706(16) 0.0174(3) Uani 1 1 d . . .
H6 H 0.4504 0.1436 0.5156 0.021 Uiso 1 1 calc R . .
C7 C 0.28343(15) 0.18203(10) 0.38981(16) 0.0208(3) Uani 1 1 d . . .
H7A H 0.3370 0.2366 0.3747 0.025 Uiso 1 1 calc R . .
H7B H 0.2446 0.1612 0.3021 0.025 Uiso 1 1 calc R . .
C8 C 0.16444(17) 0.19414(9) 0.49444(17) 0.0224(3) Uani 1 1 d . . .
H8A H 0.0753 0.2155 0.4512 0.027 Uiso 1 1 calc R . .
H8B H 0.1940 0.2352 0.5664 0.027 Uiso 1 1 calc R . .
C9 C 0.14376(16) 0.10315(9) 0.55174(16) 0.0188(3) Uani 1 1 d . . .
C10 C 0.09630(18) 0.10143(11) 0.69963(17) 0.0266(4) Uani 1 1 d . . .
H10A H 0.1054 0.0424 0.7352 0.040 Uiso 1 1 calc R . .
H10B H -0.0040 0.1201 0.7060 0.040 Uiso 1 1 calc R . .
H10C H 0.1570 0.1406 0.7529 0.040 Uiso 1 1 calc R . .
C11 C 0.03997(16) 0.05050(9) 0.46021(15) 0.0192(3) Uani 1 1 d . . .
H11 H 0.0846 0.0448 0.3682 0.023 Uiso 1 1 calc R . .
C12 C 0.01326(16) -0.03991(10) 0.51586(16) 0.0209(3) Uani 1 1 d . . .
C13 C 0.10388(18) -0.18003(9) 0.5515(2) 0.0309(4) Uani 1 1 d . . .
H13A H 0.0128 -0.2052 0.5179 0.037 Uiso 1 1 calc R . .
H13B H 0.1003 -0.1779 0.6520 0.037 Uiso 1 1 calc R . .
C14 C 0.22797(18) -0.23337(10) 0.50574(19) 0.0321(4) Uani 1 1 d . . .
H14A H 0.2327 -0.2329 0.4063 0.048 Uiso 1 1 calc R . .
H14B H 0.2159 -0.2930 0.5378 0.048 Uiso 1 1 calc R . .
H14C H 0.3170 -0.2093 0.5431 0.048 Uiso 1 1 calc R . .
O1 O 0.29969(11) -0.10705(7) 0.16442(12) 0.0260(3) Uani 1 1 d . . .
O2 O 0.35204(11) 0.01858(6) 0.26424(11) 0.0196(2) Uani 1 1 d . . .
O3 O 0.28451(10) 0.06383(6) 0.54379(11) 0.0188(2) Uani 1 1 d . . .
O4 O -0.09369(11) 0.09359(7) 0.44542(13) 0.0249(3) Uani 1 1 d . . .
H4 H -0.1460 0.0826 0.5128 0.037 Uiso 1 1 calc R . .
O5 O -0.09641(13) -0.06047(7) 0.57232(14) 0.0331(3) Uani 1 1 d . . .
O6 O 0.12410(11) -0.09335(6) 0.49619(12) 0.0234(3) 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 O1 1.2056(19) . ?
C1 O2 1.3416(17) . ?
C1 C2 1.502(2) . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O2 1.4733(17) . ?
C4 C6 1.520(2) . ?
C4 C5 1.523(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O3 1.4412(17) . ?
C6 C7 1.531(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.524(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.4468(17) . ?
C9 C10 1.521(2) . ?
C9 C11 1.551(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.4190(17) . ?
C11 C12 1.520(2) . ?
C11 H11 1.0000 . ?
C12 O5 1.2053(19) . ?
C12 O6 1.3358(18) . ?
C13 O6 1.4573(17) . ?
C13 C14 1.489(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O4 H4 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
O1 C1 O2 122.00(14) . . ?
O1 C1 C2 128.06(14) . . ?
O2 C1 C2 109.88(13) . . ?
C1 C2 C3 103.87(12) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 102.98(12) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O2 C4 C6 107.18(11) . . ?
O2 C4 C5 108.24(12) . . ?
C6 C4 C5 110.42(12) . . ?
O2 C4 C3 103.89(11) . . ?
C6 C4 C3 114.52(12) . . ?
C5 C4 C3 112.09(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 C4 110.55(11) . . ?
O3 C6 C7 105.91(11) . . ?
C4 C6 C7 115.37(13) . . ?
O3 C6 H6 108.3 . . ?
C4 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C8 C7 C6 102.26(12) . . ?
C8 C7 H7A 111.3 . . ?
C6 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C7 C8 C9 103.20(12) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
O3 C9 C10 107.92(12) . . ?
O3 C9 C8 104.60(11) . . ?
C10 C9 C8 113.97(13) . . ?
O3 C9 C11 108.25(11) . . ?
C10 C9 C11 111.43(12) . . ?
C8 C9 C11 110.28(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 C12 108.91(12) . . ?
O4 C11 C9 111.12(11) . . ?
C12 C11 C9 111.97(12) . . ?
O4 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C9 C11 H11 108.2 . . ?
O5 C12 O6 123.98(14) . . ?
O5 C12 C11 123.14(13) . . ?
O6 C12 C11 112.88(12) . . ?
O6 C13 C14 107.15(13) . . ?
O6 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O6 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O2 C4 111.57(11) . . ?
C6 O3 C9 110.99(10) . . ?
C11 O4 H4 109.5 . . ?
C12 O6 C13 114.43(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.174
_refine_diff_density_min   -0.170
_refine_diff_density_rms    0.038
