 
data_2009src0685a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C24 H32 O15'
_chemical_formula_sum
 'C24 H32 O15'
_chemical_formula_weight          560.50
_chemical_absolute_configuration  syn
 
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    'P 21 21 21'
_symmetry_space_group_name_Hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.35720(10)
_cell_length_b                    11.0999(2)
_cell_length_c                    25.9334(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2693.55(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     34056
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        fragment
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.382
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1184
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9771
_exptl_absorpt_correction_T_max   0.9885
_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: 0.882065
;
 
_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   '66.065'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             28782
_diffrn_reflns_av_R_equivalents   0.0497
_diffrn_reflns_av_sigmaI/netI     0.0330
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -33
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3484
_reflns_number_gt                 3005
_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)+(0.0108P)²+1.7276P] 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          3484
_refine_ls_number_parameters      358
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0588
_refine_ls_R_factor_gt            0.0467
_refine_ls_wR_factor_ref          0.0897
_refine_ls_wR_factor_gt           0.0840
_refine_ls_goodness_of_fit_ref    1.152
_refine_ls_restrained_S_all       1.152
_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 0.4951(3) 0.5645(3) 0.35538(10) 0.0263(6) Uani 1 1 d . . .
H1 H 0.4144 0.6201 0.3469 0.032 Uiso 1 1 calc R . .
C2 C 0.5596(3) 0.5156(3) 0.30555(11) 0.0252(6) Uani 1 1 d . . .
H2 H 0.4837 0.4754 0.2845 0.030 Uiso 1 1 calc R . .
C3 C 0.6268(3) 0.6182(3) 0.27470(10) 0.0233(6) Uani 1 1 d . . .
H3 H 0.5494 0.6703 0.2602 0.028 Uiso 1 1 calc R . .
C4 C 0.7253(3) 0.6944(3) 0.30749(10) 0.0227(6) Uani 1 1 d . . .
H4 H 0.8146 0.6490 0.3159 0.027 Uiso 1 1 calc R . .
C5 C 0.6485(3) 0.7324(3) 0.35673(10) 0.0261(6) Uani 1 1 d . . .
H5 H 0.5660 0.7865 0.3486 0.031 Uiso 1 1 calc R . .
C6 C 0.4427(3) 0.4669(3) 0.39123(11) 0.0319(7) Uani 1 1 d . . .
H6A H 0.5176 0.4050 0.3962 0.038 Uiso 1 1 calc R . .
H6B H 0.4176 0.5014 0.4253 0.038 Uiso 1 1 calc R . .
C7 C 0.2656(4) 0.3139(3) 0.38940(13) 0.0376(8) Uani 1 1 d . . .
C8 C 0.1324(4) 0.2726(3) 0.36343(13) 0.0418(8) Uani 1 1 d . . .
H8A H 0.1560 0.2396 0.3294 0.063 Uiso 1 1 calc R . .
H8B H 0.0671 0.3410 0.3593 0.063 Uiso 1 1 calc R . .
H8C H 0.0865 0.2102 0.3844 0.063 Uiso 1 1 calc R . .
C9 C 0.6785(3) 0.3280(3) 0.29079(12) 0.0299(7) Uani 1 1 d . . .
C10 C 0.7758(4) 0.2388(3) 0.31523(14) 0.0411(8) Uani 1 1 d . . .
H10A H 0.7266 0.1612 0.3184 0.062 Uiso 1 1 calc R . .
H10B H 0.8034 0.2674 0.3496 0.062 Uiso 1 1 calc R . .
H10C H 0.8614 0.2290 0.2939 0.062 Uiso 1 1 calc R . .
C11 C 0.6384(3) 0.5379(3) 0.18986(11) 0.0315(7) Uani 1 1 d . . .
C12 C 0.7316(4) 0.4765(3) 0.15169(12) 0.0393(8) Uani 1 1 d . . .
H12A H 0.7251 0.3891 0.1565 0.059 Uiso 1 1 calc R . .
H12B H 0.8307 0.5025 0.1566 0.059 Uiso 1 1 calc R . .
H12C H 0.7004 0.4974 0.1167 0.059 Uiso 1 1 calc R . .
C13 C 0.8990(3) 0.8312(3) 0.27365(11) 0.0308(7) Uani 1 1 d . . .
C14 C 0.9148(4) 0.9563(3) 0.25297(15) 0.0483(9) Uani 1 1 d . . .
H14A H 0.9110 1.0141 0.2815 0.072 Uiso 1 1 calc R . .
H14B H 0.8370 0.9731 0.2287 0.072 Uiso 1 1 calc R . .
H14C H 1.0067 0.9636 0.2351 0.072 Uiso 1 1 calc R . .
C15 C 0.6847(3) 0.8615(3) 0.42865(10) 0.0245(6) Uani 1 1 d . . .
H15 H 0.5819 0.8393 0.4332 0.029 Uiso 1 1 calc R . .
C16 C 0.6984(3) 0.9940(3) 0.41488(11) 0.0275(7) Uani 1 1 d . . .
H16 H 0.6483 1.0072 0.3813 0.033 Uiso 1 1 calc R . .
C17 C 0.9377(3) 0.9807(3) 0.44371(11) 0.0308(7) Uani 1 1 d . . .
H17 H 1.0312 1.0140 0.4448 0.037 Uiso 1 1 calc R . .
C18 C 0.9094(3) 0.8929(3) 0.47714(11) 0.0265(6) Uani 1 1 d . . .
H18 H 0.9799 0.8705 0.5017 0.032 Uiso 1 1 calc R . .
C19 C 0.7697(3) 0.8291(3) 0.47687(10) 0.0246(6) Uani 1 1 d . . .
H19 H 0.7864 0.7401 0.4777 0.030 Uiso 1 1 calc R . .
C20 C 0.6361(3) 1.0808(3) 0.45385(11) 0.0292(7) Uani 1 1 d . . .
H20A H 0.6919 1.0783 0.4863 0.035 Uiso 1 1 calc R . .
H20B H 0.6389 1.1641 0.4402 0.035 Uiso 1 1 calc R . .
C21 C 0.4292(4) 1.0907(4) 0.50596(12) 0.0423(9) Uani 1 1 d . . .
C22 C 0.2779(4) 1.0487(4) 0.51205(14) 0.0453(9) Uani 1 1 d . . .
H22A H 0.2610 1.0258 0.5480 0.068 Uiso 1 1 calc R . .
H22B H 0.2614 0.9789 0.4897 0.068 Uiso 1 1 calc R . .
H22C H 0.2125 1.1138 0.5024 0.068 Uiso 1 1 calc R . .
C23 C 0.7065(3) 0.8109(3) 0.56586(11) 0.0287(7) Uani 1 1 d . . .
C24 C 0.5991(3) 0.8462(3) 0.60543(11) 0.0337(7) Uani 1 1 d . . .
H24A H 0.5102 0.8015 0.5996 0.051 Uiso 1 1 calc R . .
H24B H 0.5802 0.9328 0.6029 0.051 Uiso 1 1 calc R . .
H24C H 0.6361 0.8275 0.6399 0.051 Uiso 1 1 calc R . .
O1 O 0.6014(2) 0.62851(19) 0.38388(7) 0.0284(5) Uani 1 1 d . . .
O2 O 0.3179(2) 0.41451(19) 0.36712(8) 0.0317(5) Uani 1 1 d . . .
O3 O 0.3222(3) 0.2686(3) 0.42648(11) 0.0621(8) Uani 1 1 d . . .
O4 O 0.6668(2) 0.42849(18) 0.32027(7) 0.0263(4) Uani 1 1 d . . .
O5 O 0.6163(3) 0.3147(2) 0.25060(8) 0.0362(5) Uani 1 1 d . . .
O6 O 0.7123(2) 0.57056(17) 0.23281(7) 0.0232(4) Uani 1 1 d . . .
O7 O 0.5135(3) 0.5562(3) 0.18488(9) 0.0498(7) Uani 1 1 d . . .
O8 O 0.7588(2) 0.80299(18) 0.27956(7) 0.0261(5) Uani 1 1 d . . .
O9 O 0.9956(2) 0.7643(2) 0.28413(9) 0.0427(6) Uani 1 1 d . . .
O10 O 0.7476(2) 0.7917(2) 0.38757(7) 0.0303(5) Uani 1 1 d . . .
O11 O 0.8463(2) 1.0275(2) 0.40824(8) 0.0324(5) Uani 1 1 d . . .
O12 O 0.4906(2) 1.04471(19) 0.46333(8) 0.0292(5) Uani 1 1 d . . .
O13 O 0.4901(3) 1.1562(4) 0.53487(11) 0.0840(12) Uani 1 1 d . . .
O14 O 0.6770(2) 0.86348(18) 0.52019(7) 0.0270(4) Uani 1 1 d . . .
O15 O 0.8074(3) 0.7450(2) 0.57225(8) 0.0392(6) 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 1.428(3) . ?
C1 C6 1.509(4) . ?
C1 C2 1.526(4) . ?
C1 H1 1.0000 . ?
C2 O4 1.445(3) . ?
C2 C3 1.528(4) . ?
C2 H2 1.0000 . ?
C3 O6 1.449(3) . ?
C3 C4 1.513(4) . ?
C3 H3 1.0000 . ?
C4 O8 1.440(3) . ?
C4 C5 1.525(4) . ?
C4 H4 1.0000 . ?
C5 O10 1.390(3) . ?
C5 O1 1.421(4) . ?
C5 H5 1.0000 . ?
C6 O2 1.447(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.207(4) . ?
C7 O2 1.349(4) . ?
C7 C8 1.489(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O5 1.203(4) . ?
C9 O4 1.357(3) . ?
C9 C10 1.486(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O7 1.194(4) . ?
C11 O6 1.360(3) . ?
C11 C12 1.485(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O9 1.201(4) . ?
C13 O8 1.358(4) . ?
C13 C14 1.495(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O10 1.443(3) . ?
C15 C16 1.519(4) . ?
C15 C19 1.525(4) . ?
C15 H15 1.0000 . ?
C16 O11 1.443(3) . ?
C16 C20 1.513(4) . ?
C16 H16 1.0000 . ?
C17 C18 1.331(4) . ?
C17 O11 1.359(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.487(4) . ?
C18 H18 0.9500 . ?
C19 O14 1.470(3) . ?
C19 H19 1.0000 . ?
C20 O12 1.441(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O13 1.189(4) . ?
C21 O12 1.347(4) . ?
C21 C22 1.499(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O15 1.205(4) . ?
C23 O14 1.349(3) . ?
C23 C24 1.489(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 C6 105.3(2) . . ?
O1 C1 C2 109.9(2) . . ?
C6 C1 C2 113.2(3) . . ?
O1 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O4 C2 C1 106.8(2) . . ?
O4 C2 C3 110.5(2) . . ?
C1 C2 C3 109.9(2) . . ?
O4 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
O6 C3 C4 106.8(2) . . ?
O6 C3 C2 110.4(2) . . ?
C4 C3 C2 112.0(2) . . ?
O6 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O8 C4 C3 108.5(2) . . ?
O8 C4 C5 107.0(2) . . ?
C3 C4 C5 109.8(2) . . ?
O8 C4 H4 110.5 . . ?
C3 C4 H4 110.5 . . ?
C5 C4 H4 110.5 . . ?
O10 C5 O1 107.8(2) . . ?
O10 C5 C4 107.4(2) . . ?
O1 C5 C4 109.7(2) . . ?
O10 C5 H5 110.6 . . ?
O1 C5 H5 110.6 . . ?
C4 C5 H5 110.6 . . ?
O2 C6 C1 106.5(2) . . ?
O2 C6 H6A 110.4 . . ?
C1 C6 H6A 110.4 . . ?
O2 C6 H6B 110.4 . . ?
C1 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O3 C7 O2 121.8(3) . . ?
O3 C7 C8 126.8(3) . . ?
O2 C7 C8 111.4(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 123.4(3) . . ?
O5 C9 C10 125.7(3) . . ?
O4 C9 C10 110.9(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 122.8(3) . . ?
O7 C11 C12 125.5(3) . . ?
O6 C11 C12 111.7(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 124.0(3) . . ?
O9 C13 C14 125.5(3) . . ?
O8 C13 C14 110.5(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 . . ?
O10 C15 C16 108.2(2) . . ?
O10 C15 C19 105.4(2) . . ?
C16 C15 C19 112.2(2) . . ?
O10 C15 H15 110.3 . . ?
C16 C15 H15 110.3 . . ?
C19 C15 H15 110.3 . . ?
O11 C16 C20 106.6(2) . . ?
O11 C16 C15 111.0(2) . . ?
C20 C16 C15 115.3(2) . . ?
O11 C16 H16 107.9 . . ?
C20 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C18 C17 O11 126.5(3) . . ?
C18 C17 H17 116.7 . . ?
O11 C17 H17 116.7 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
O14 C19 C18 113.0(2) . . ?
O14 C19 C15 105.0(2) . . ?
C18 C19 C15 110.5(2) . . ?
O14 C19 H19 109.4 . . ?
C18 C19 H19 109.4 . . ?
C15 C19 H19 109.4 . . ?
O12 C20 C16 107.5(2) . . ?
O12 C20 H20A 110.2 . . ?
C16 C20 H20A 110.2 . . ?
O12 C20 H20B 110.2 . . ?
C16 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
O13 C21 O12 123.0(3) . . ?
O13 C21 C22 125.2(3) . . ?
O12 C21 C22 111.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O15 C23 O14 122.9(3) . . ?
O15 C23 C24 126.4(3) . . ?
O14 C23 C24 110.7(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 O1 C1 111.3(2) . . ?
C7 O2 C6 116.1(2) . . ?
C9 O4 C2 117.2(2) . . ?
C11 O6 C3 115.5(2) . . ?
C13 O8 C4 117.4(2) . . ?
C5 O10 C15 114.0(2) . . ?
C17 O11 C16 115.1(2) . . ?
C21 O12 C20 116.0(3) . . ?
C23 O14 C19 116.0(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.249
_refine_diff_density_min   -0.216
_refine_diff_density_rms    0.048
