 
data_2009src0671
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C21 H26 O9 S'
_chemical_formula_sum
 'C21 H26 O9 S'
_chemical_formula_weight          454.48
_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    'C 2'
_symmetry_space_group_name_Hall   'C 2y'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 
_cell_length_a                    18.9488(6)
_cell_length_b                    5.60240(10)
_cell_length_c                    20.7934(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.355(2)
_cell_angle_gamma                 90.00
_cell_volume                      2207.36(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     9591
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.368
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              960
_exptl_absorpt_coefficient_mu     0.196
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9712
_exptl_absorpt_correction_T_max   0.9961
_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: 0.911645
;
 
_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   66.0645
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             10898
_diffrn_reflns_av_R_equivalents   0.0523
_diffrn_reflns_av_sigmaI/netI     0.0802
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        24
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4782
_reflns_number_gt                 3858
_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+4.9839P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.08(12)
_refine_ls_number_reflns          4782
_refine_ls_number_parameters      284
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0869
_refine_ls_R_factor_gt            0.0617
_refine_ls_wR_factor_ref          0.1233
_refine_ls_wR_factor_gt           0.1100
_refine_ls_goodness_of_fit_ref    1.102
_refine_ls_restrained_S_all       1.102
_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 0.26099(19) 0.9177(7) 0.18255(16) 0.0202(8) Uani 1 1 d . . .
H1 H 0.2868 1.0639 0.1971 0.024 Uiso 1 1 calc R . .
C2 C 0.30956(19) 0.7624(7) 0.14222(16) 0.0200(8) Uani 1 1 d . . .
H2 H 0.2844 0.6158 0.1270 0.024 Uiso 1 1 calc R . .
C3 C 0.37455(18) 0.6965(6) 0.18242(15) 0.0179(7) Uani 1 1 d . . .
H3 H 0.4048 0.8402 0.1899 0.021 Uiso 1 1 calc R . .
C4 C 0.35233(17) 0.5870(7) 0.24614(15) 0.0185(7) Uani 1 1 d . . .
H4 H 0.3340 0.4220 0.2384 0.022 Uiso 1 1 calc R . .
C5 C 0.29608(18) 0.7343(7) 0.27989(16) 0.0194(8) Uani 1 1 d . . .
H5 H 0.3167 0.8864 0.2967 0.023 Uiso 1 1 calc R . .
C6 C 0.1950(2) 0.9887(7) 0.14582(17) 0.0238(8) Uani 1 1 d . . .
H6A H 0.2068 1.0201 0.1003 0.029 Uiso 1 1 calc R . .
H6B H 0.1602 0.8569 0.1471 0.029 Uiso 1 1 calc R . .
C7 C 0.1083(2) 1.1730(7) 0.21344(17) 0.0233(8) Uani 1 1 d . . .
C8 C 0.0847(2) 1.4070(7) 0.23945(18) 0.0261(8) Uani 1 1 d . . .
H8A H 0.0679 1.5080 0.2041 0.039 Uiso 1 1 calc R . .
H8B H 0.1244 1.4856 0.2613 0.039 Uiso 1 1 calc R . .
H8C H 0.0464 1.3814 0.2701 0.039 Uiso 1 1 calc R . .
C9 C 0.33273(19) 0.8025(7) 0.02888(16) 0.0209(8) Uani 1 1 d . . .
C10 C 0.3599(2) 0.9730(7) -0.02014(17) 0.0275(9) Uani 1 1 d . . .
H10A H 0.4109 0.9509 -0.0249 0.041 Uiso 1 1 calc R . .
H10B H 0.3502 1.1369 -0.0062 0.041 Uiso 1 1 calc R . .
H10C H 0.3363 0.9432 -0.0615 0.041 Uiso 1 1 calc R . .
C11 C 0.47170(18) 0.5759(8) 0.11559(16) 0.0228(8) Uani 1 1 d . . .
C12 C 0.5052(2) 0.3592(8) 0.08709(19) 0.0312(10) Uani 1 1 d . . .
H12A H 0.5447 0.4075 0.0597 0.047 Uiso 1 1 calc R . .
H12B H 0.4703 0.2724 0.0612 0.047 Uiso 1 1 calc R . .
H12C H 0.5227 0.2555 0.1216 0.047 Uiso 1 1 calc R . .
C13 C 0.43729(19) 0.3566(7) 0.30531(17) 0.0236(8) Uani 1 1 d . . .
C14 C 0.4955(2) 0.3766(8) 0.35387(18) 0.0280(9) Uani 1 1 d . . .
H14A H 0.4760 0.4279 0.3952 0.042 Uiso 1 1 calc R . .
H14B H 0.5302 0.4940 0.3392 0.042 Uiso 1 1 calc R . .
H14C H 0.5185 0.2210 0.3591 0.042 Uiso 1 1 calc R . .
C15 C 0.1984(2) 0.7593(7) 0.38000(17) 0.0247(8) Uani 1 1 d . . .
H15A H 0.2221 0.9087 0.3937 0.030 Uiso 1 1 calc R . .
H15B H 0.1614 0.7997 0.3481 0.030 Uiso 1 1 calc R . .
C16 C 0.16633(19) 0.6350(7) 0.43727(17) 0.0222(8) Uani 1 1 d . . .
C17 C 0.1261(2) 0.4288(7) 0.42932(18) 0.0278(9) Uani 1 1 d . . .
H17 H 0.1177 0.3674 0.3874 0.033 Uiso 1 1 calc R . .
C18 C 0.0982(2) 0.3126(8) 0.48226(19) 0.0313(9) Uani 1 1 d . . .
H18 H 0.0712 0.1714 0.4763 0.038 Uiso 1 1 calc R . .
C19 C 0.1094(2) 0.4007(8) 0.54368(18) 0.0308(9) Uani 1 1 d . . .
H19 H 0.0901 0.3210 0.5799 0.037 Uiso 1 1 calc R . .
C20 C 0.1490(2) 0.6066(8) 0.55175(18) 0.0298(9) Uani 1 1 d . . .
H20 H 0.1565 0.6686 0.5938 0.036 Uiso 1 1 calc R . .
C21 C 0.1778(2) 0.7231(7) 0.49937(18) 0.0261(9) Uani 1 1 d . . .
H21 H 0.2053 0.8629 0.5056 0.031 Uiso 1 1 calc R . .
O1 O 0.23884(13) 0.7830(5) 0.23693(11) 0.0209(6) Uani 1 1 d . . .
O2 O 0.16485(13) 1.2014(5) 0.17444(12) 0.0250(6) Uani 1 1 d . . .
O3 O 0.08147(15) 0.9813(5) 0.22390(13) 0.0298(7) Uani 1 1 d . . .
O4 O 0.33298(13) 0.9046(4) 0.08822(11) 0.0204(5) Uani 1 1 d . . .
O5 O 0.31455(16) 0.6003(5) 0.01895(12) 0.0376(7) Uani 1 1 d . . .
O6 O 0.41400(12) 0.5121(4) 0.14999(11) 0.0218(6) Uani 1 1 d . . .
O7 O 0.49107(15) 0.7787(5) 0.10971(13) 0.0305(7) Uani 1 1 d . . .
O8 O 0.41336(11) 0.5753(5) 0.28813(10) 0.0193(5) Uani 1 1 d . . .
O9 O 0.41318(14) 0.1722(5) 0.28535(13) 0.0301(6) Uani 1 1 d . . .
S1 S 0.26211(5) 0.55551(17) 0.34510(4) 0.0244(2) 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 1.425(4) . ?
C1 C6 1.514(5) . ?
C1 C2 1.522(5) . ?
C1 H1 1.0000 . ?
C2 O4 1.449(4) . ?
C2 C3 1.529(5) . ?
C2 H2 1.0000 . ?
C3 O6 1.445(4) . ?
C3 C4 1.522(5) . ?
C3 H3 1.0000 . ?
C4 O8 1.446(4) . ?
C4 C5 1.523(5) . ?
C4 H4 1.0000 . ?
C5 O1 1.427(4) . ?
C5 S1 1.807(3) . ?
C5 H5 1.0000 . ?
C6 O2 1.451(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.209(4) . ?
C7 O2 1.357(4) . ?
C7 C8 1.488(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O5 1.202(5) . ?
C9 O4 1.360(4) . ?
C9 C10 1.491(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O7 1.201(5) . ?
C11 O6 1.358(4) . ?
C11 C12 1.494(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O9 1.203(5) . ?
C13 O8 1.354(5) . ?
C13 C14 1.495(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.511(5) . ?
C15 S1 1.816(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.394(5) . ?
C16 C21 1.398(5) . ?
C17 C18 1.386(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
 
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 C6 107.0(3) . . ?
O1 C1 C2 108.4(3) . . ?
C6 C1 C2 111.9(3) . . ?
O1 C1 H1 109.8 . . ?
C6 C1 H1 109.8 . . ?
C2 C1 H1 109.8 . . ?
O4 C2 C1 107.6(3) . . ?
O4 C2 C3 107.9(3) . . ?
C1 C2 C3 108.9(3) . . ?
O4 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
O6 C3 C4 105.3(3) . . ?
O6 C3 C2 109.6(3) . . ?
C4 C3 C2 110.3(3) . . ?
O6 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
O8 C4 C3 108.6(3) . . ?
O8 C4 C5 107.8(3) . . ?
C3 C4 C5 112.4(3) . . ?
O8 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
O1 C5 C4 110.3(3) . . ?
O1 C5 S1 107.6(2) . . ?
C4 C5 S1 107.4(2) . . ?
O1 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
S1 C5 H5 110.5 . . ?
O2 C6 C1 109.6(3) . . ?
O2 C6 H6A 109.8 . . ?
C1 C6 H6A 109.8 . . ?
O2 C6 H6B 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
O3 C7 O2 123.1(4) . . ?
O3 C7 C8 126.2(3) . . ?
O2 C7 C8 110.7(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 O4 123.5(3) . . ?
O5 C9 C10 125.9(3) . . ?
O4 C9 C10 110.6(3) . . ?
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 . . ?
O7 C11 O6 123.4(3) . . ?
O7 C11 C12 126.7(3) . . ?
O6 C11 C12 109.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O9 C13 O8 124.1(3) . . ?
O9 C13 C14 125.1(4) . . ?
O8 C13 C14 110.8(3) . . ?
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 . . ?
C16 C15 S1 107.3(3) . . ?
C16 C15 H15A 110.3 . . ?
S1 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
S1 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C17 C16 C21 118.9(3) . . ?
C17 C16 C15 120.8(3) . . ?
C21 C16 C15 120.3(3) . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C16 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C1 O1 C5 111.8(3) . . ?
C7 O2 C6 117.6(3) . . ?
C9 O4 C2 118.2(3) . . ?
C11 O6 C3 118.6(3) . . ?
C13 O8 C4 117.7(3) . . ?
C5 S1 C15 101.07(17) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.321
_refine_diff_density_min   -0.313
_refine_diff_density_rms    0.075
