 
data_2009src0666
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C20 H24 O9 S'
_chemical_formula_sum
 'C20 H24 O9 S'
_chemical_formula_weight          440.45
_chemical_absolute_configuration  ad
 
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'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21'
_symmetry_space_group_name_Hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    12.0167(3)
_cell_length_b                    5.56050(10)
_cell_length_c                    17.6399(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.850(2)
_cell_angle_gamma                 90.00
_cell_volume                      1108.65(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11974
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              464
_exptl_absorpt_coefficient_mu     0.193
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9624
_exptl_absorpt_correction_T_max   0.9904
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
 Ratio of minimum to maximum apparent transmission: 0.870271
;
 
_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    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             13739
_diffrn_reflns_av_R_equivalents   0.0422
_diffrn_reflns_av_sigmaI/netI     0.0507
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.39
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4613
_reflns_number_gt                 4201
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0000P)²+0.8048P] 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_abs_structure_details  'Flack (1983), 1833 Friedel pairs'
_refine_ls_abs_structure_Flack    0.12(8)
_refine_ls_number_reflns          4613
_refine_ls_number_parameters      275
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0513
_refine_ls_R_factor_gt            0.0441
_refine_ls_wR_factor_ref          0.0876
_refine_ls_wR_factor_gt           0.0836
_refine_ls_goodness_of_fit_ref    1.075
_refine_ls_restrained_S_all       1.075
_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 0.8056(2) 0.4348(4) 0.78826(13) 0.0170(5) Uani 1 1 d . . .
H1 H 0.8220 0.5844 0.8217 0.020 Uiso 1 1 calc R . .
C2 C 0.92195(19) 0.3244(4) 0.78764(13) 0.0170(5) Uani 1 1 d . . .
H2 H 0.9076 0.1611 0.7624 0.020 Uiso 1 1 calc R . .
C3 C 0.9825(2) 0.4858(4) 0.74352(14) 0.0173(5) Uani 1 1 d . . .
H3 H 1.0194 0.6254 0.7788 0.021 Uiso 1 1 calc R . .
C4 C 0.8991(2) 0.5799(4) 0.66278(14) 0.0180(5) Uani 1 1 d . . .
H4 H 0.9388 0.7110 0.6427 0.022 Uiso 1 1 calc R . .
C5 C 0.7884(2) 0.6780(4) 0.67581(13) 0.0175(5) Uani 1 1 d . . .
H5 H 0.8123 0.8113 0.7161 0.021 Uiso 1 1 calc R . .
C6 C 0.6186(2) 0.4008(5) 0.84762(14) 0.0208(5) Uani 1 1 d . . .
C7 C 0.5740(2) 0.6112(5) 0.80632(16) 0.0248(5) Uani 1 1 d . . .
H7 H 0.6048 0.6710 0.7670 0.030 Uiso 1 1 calc R . .
C8 C 0.4838(2) 0.7348(6) 0.82270(16) 0.0305(6) Uani 1 1 d . . .
H8 H 0.4539 0.8800 0.7948 0.037 Uiso 1 1 calc R . .
C9 C 0.4373(2) 0.6480(6) 0.87923(16) 0.0334(7) Uani 1 1 d . . .
H9 H 0.3750 0.7318 0.8896 0.040 Uiso 1 1 calc R . .
C10 C 0.4820(2) 0.4394(6) 0.92036(16) 0.0342(7) Uani 1 1 d . . .
H10 H 0.4501 0.3791 0.9591 0.041 Uiso 1 1 calc R . .
C11 C 0.5731(2) 0.3164(6) 0.90576(16) 0.0295(6) Uani 1 1 d . . .
H11 H 0.6046 0.1747 0.9353 0.035 Uiso 1 1 calc R . .
C12 C 0.6965(2) 0.7718(4) 0.60033(14) 0.0206(6) Uani 1 1 d . . .
H12A H 0.7329 0.8828 0.5716 0.025 Uiso 1 1 calc R . .
H12B H 0.6590 0.6374 0.5638 0.025 Uiso 1 1 calc R . .
C13 C 0.5611(2) 1.0965(5) 0.58364(14) 0.0192(5) Uani 1 1 d . . .
C14 C 0.4723(2) 1.2023(6) 0.61623(14) 0.0268(6) Uani 1 1 d . . .
H14A H 0.4014 1.1007 0.6008 0.040 Uiso 1 1 calc R . .
H14B H 0.4509 1.3642 0.5941 0.040 Uiso 1 1 calc R . .
H14C H 0.5062 1.2114 0.6751 0.040 Uiso 1 1 calc R . .
C15 C 0.8626(2) 0.4378(5) 0.52883(14) 0.0210(5) Uani 1 1 d . . .
C16 C 0.8309(2) 0.2205(5) 0.47608(14) 0.0260(5) Uani 1 1 d . . .
H16A H 0.8398 0.2564 0.4240 0.039 Uiso 1 1 calc R . .
H16B H 0.7487 0.1753 0.4676 0.039 Uiso 1 1 calc R . .
H16C H 0.8834 0.0873 0.5020 0.039 Uiso 1 1 calc R . .
C17 C 1.1676(2) 0.4579(5) 0.72235(15) 0.0226(5) Uani 1 1 d . . .
C18 C 1.2513(2) 0.2847(5) 0.70507(17) 0.0309(7) Uani 1 1 d . . .
H18A H 1.3311 0.3533 0.7233 0.046 Uiso 1 1 calc R . .
H18B H 1.2259 0.2539 0.6470 0.046 Uiso 1 1 calc R . .
H18C H 1.2516 0.1334 0.7336 0.046 Uiso 1 1 calc R . .
C19 C 1.0281(2) 0.0879(5) 0.90354(14) 0.0215(5) Uani 1 1 d . . .
C20 C 1.1165(3) 0.1071(6) 0.98702(16) 0.0377(7) Uani 1 1 d . . .
H20A H 1.1475 -0.0531 1.0062 0.057 Uiso 1 1 calc R . .
H20B H 1.0781 0.1749 1.0231 0.057 Uiso 1 1 calc R . .
H20C H 1.1817 0.2120 0.9864 0.057 Uiso 1 1 calc R . .
O1 O 0.73444(14) 0.4903(3) 0.70754(9) 0.0174(4) Uani 1 1 d . . .
O2 O 0.60989(14) 0.8969(3) 0.62567(10) 0.0221(4) Uani 1 1 d . . .
O3 O 0.58653(14) 1.1737(3) 0.52788(10) 0.0237(4) Uani 1 1 d . . .
O4 O 0.86905(14) 0.3836(3) 0.60561(9) 0.0190(4) Uani 1 1 d . . .
O5 O 0.87856(18) 0.6360(3) 0.50817(11) 0.0318(5) Uani 1 1 d . . .
O6 O 1.07465(14) 0.3383(3) 0.73250(10) 0.0208(4) Uani 1 1 d . . .
O7 O 1.17586(15) 0.6722(3) 0.72542(11) 0.0294(4) Uani 1 1 d . . .
O8 O 1.00372(14) 0.3092(3) 0.86967(9) 0.0195(4) Uani 1 1 d . . .
O9 O 0.98235(17) -0.0939(3) 0.87050(11) 0.0303(4) Uani 1 1 d . . .
S1 S 0.72846(5) 0.21988(11) 0.82901(3) 0.02017(13) Uani 1 1 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 O1 1.424(3) . ?
C1 C2 1.530(3) . ?
C1 S1 1.805(2) . ?
C1 H1 1.0000 . ?
C2 O8 1.449(3) . ?
C2 C3 1.525(3) . ?
C2 H2 1.0000 . ?
C3 O6 1.443(3) . ?
C3 C4 1.529(3) . ?
C3 H3 1.0000 . ?
C4 O4 1.446(3) . ?
C4 C5 1.524(3) . ?
C4 H4 1.0000 . ?
C5 O1 1.439(3) . ?
C5 C12 1.506(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.387(4) . ?
C6 C11 1.397(3) . ?
C6 S1 1.777(3) . ?
C7 C8 1.394(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O2 1.443(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.204(3) . ?
C13 O2 1.353(3) . ?
C13 C14 1.495(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O5 1.197(3) . ?
C15 O4 1.364(3) . ?
C15 C16 1.493(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O7 1.196(3) . ?
C17 O6 1.362(3) . ?
C17 C18 1.497(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O9 1.202(3) . ?
C19 O8 1.356(3) . ?
C19 C20 1.499(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
 
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 C2 108.66(17) . . ?
O1 C1 S1 109.04(15) . . ?
C2 C1 S1 109.35(17) . . ?
O1 C1 H1 109.9 . . ?
C2 C1 H1 109.9 . . ?
S1 C1 H1 109.9 . . ?
O8 C2 C3 105.34(18) . . ?
O8 C2 C1 109.12(18) . . ?
C3 C2 C1 111.26(19) . . ?
O8 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
O6 C3 C2 104.77(19) . . ?
O6 C3 C4 111.07(18) . . ?
C2 C3 C4 113.66(19) . . ?
O6 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
O4 C4 C5 110.57(19) . . ?
O4 C4 C3 108.69(19) . . ?
C5 C4 C3 108.15(18) . . ?
O4 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
O1 C5 C12 107.63(18) . . ?
O1 C5 C4 109.32(19) . . ?
C12 C5 C4 113.97(18) . . ?
O1 C5 H5 108.6 . . ?
C12 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C7 C6 C11 119.4(2) . . ?
C7 C6 S1 124.05(19) . . ?
C11 C6 S1 116.5(2) . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
O2 C12 C5 106.45(18) . . ?
O2 C12 H12A 110.4 . . ?
C5 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
C5 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
O3 C13 O2 123.9(2) . . ?
O3 C13 C14 125.9(2) . . ?
O2 C13 C14 110.2(2) . . ?
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 . . ?
O5 C15 O4 123.0(2) . . ?
O5 C15 C16 126.1(2) . . ?
O4 C15 C16 110.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O7 C17 O6 122.7(2) . . ?
O7 C17 C18 126.8(2) . . ?
O6 C17 C18 110.5(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O9 C19 O8 123.7(2) . . ?
O9 C19 C20 126.2(3) . . ?
O8 C19 C20 110.1(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O1 C5 110.43(17) . . ?
C13 O2 C12 116.69(18) . . ?
C15 O4 C4 116.26(19) . . ?
C17 O6 C3 116.1(2) . . ?
C19 O8 C2 117.67(18) . . ?
C6 S1 C1 102.31(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.354
_refine_diff_density_min   -0.259
_refine_diff_density_rms    0.056
