 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C25 H30 O7'
_chemical_absolute_configuration   unk
_chemical_formula_weight          442.49
 
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    P21
_symmetry_space_group_name_hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    9.2535(3)
_cell_length_b                    13.1779(4)
_cell_length_c                    9.6444(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  113.1490(10)
_cell_angle_gamma                 90.00
_cell_volume                      1081.36(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unknown
_exptl_crystal_colour             unknown
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.25
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.359
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              472
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.9616
_exptl_absorpt_correction_T_max   0.9757
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             19743
_diffrn_reflns_av_R_equivalents   0.0609
_diffrn_reflns_av_sigmaI/netI     0.0445
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.30
_diffrn_reflns_theta_max          26.37
_reflns_number_total              4408
_reflns_number_gt                 3905
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0510P)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     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.025(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4408
_refine_ls_number_parameters      410
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0445
_refine_ls_R_factor_gt            0.0369
_refine_ls_wR_factor_ref          0.0855
_refine_ls_wR_factor_gt           0.0817
_refine_ls_goodness_of_fit_ref    1.039
_refine_ls_restrained_S_all       1.039
_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
O4 O 0.05251(14) 0.14822(10) 0.37771(13) 0.0275(3) Uani 1 1 d . . .
O1 O -0.31159(15) 0.42262(9) -1.07706(13) 0.0267(3) Uani 1 1 d . . .
O2 O -0.48334(15) 0.28882(10) -1.01786(13) 0.0280(3) Uani 1 1 d . . .
O3 O -0.16696(16) 0.01437(10) 0.32512(13) 0.0301(3) Uani 1 1 d . . .
O6 O -0.26888(15) 0.09172(9) -0.33410(13) 0.0231(3) Uani 1 1 d . . .
O7 O 0.03734(14) 0.19770(11) -0.16883(13) 0.0306(3) Uani 1 1 d . . .
C7 C -0.1287(2) 0.42964(13) -0.6605(2) 0.0228(4) Uani 1 1 d . . .
C10 C -0.3670(2) 0.33136(13) -0.89529(19) 0.0207(4) Uani 1 1 d . . .
O5 O -0.33259(17) 0.35400(10) -0.44036(15) 0.0316(3) Uani 1 1 d . . .
C21 C -0.2502(2) 0.03120(14) 0.05263(19) 0.0234(4) Uani 1 1 d . . .
C17 C -0.1287(2) 0.16157(12) -0.03891(19) 0.0204(4) Uani 1 1 d . . .
C20 C -0.1574(2) 0.05756(14) 0.19989(19) 0.0231(4) Uani 1 1 d . . .
C5 C -0.2739(2) 0.40476(13) -0.92761(19) 0.0215(4) Uani 1 1 d . . .
C19 C -0.0424(2) 0.13312(14) 0.22880(19) 0.0231(4) Uani 1 1 d . . .
C9 C -0.3384(2) 0.30823(13) -0.7469(2) 0.0229(4) Uani 1 1 d . . .
C16 C -0.1114(2) 0.22152(14) -0.16281(19) 0.0211(4) Uani 1 1 d . . .
C22 C -0.2330(2) 0.08112(13) -0.06881(18) 0.0217(4) Uani 1 1 d . . .
C12 C -0.1473(2) 0.22267(13) -0.42102(19) 0.0221(4) Uani 1 1 d . . .
C1 C -0.2190(3) 0.49655(15) -1.1141(2) 0.0293(4) Uani 1 1 d . . .
C11 C -0.1923(2) 0.33354(13) -0.4675(2) 0.0241(4) Uani 1 1 d . . .
C2 C -0.5752(2) 0.21102(15) -0.9893(2) 0.0281(4) Uani 1 1 d . . .
C13 C -0.2338(2) 0.19699(13) -0.31981(18) 0.0211(4) Uani 1 1 d . . .
C18 C -0.0329(2) 0.18636(14) 0.11029(18) 0.0218(4) Uani 1 1 d . . .
C6 C -0.1552(2) 0.45285(13) -0.8108(2) 0.0234(4) Uani 1 1 d . . .
C8 C -0.2184(2) 0.35772(13) -0.62797(19) 0.0222(4) Uani 1 1 d . . .
C4 C 0.1755(2) 0.22025(17) 0.4070(2) 0.0316(4) Uani 1 1 d . . .
C15 C 0.0265(2) 0.20677(15) -0.32123(19) 0.0270(4) Uani 1 1 d . . .
C3 C -0.3047(3) -0.04288(19) 0.3051(3) 0.0361(5) Uani 1 1 d . . .
C23 C -0.3274(2) 0.04623(13) -0.22905(19) 0.0226(4) Uani 1 1 d . . .
C14 C -0.3772(2) 0.26715(15) -0.3777(2) 0.0263(4) Uani 1 1 d . . .
C25 C -0.5021(2) 0.06771(16) -0.2772(2) 0.0288(4) Uani 1 1 d . . .
C24 C -0.3013(3) -0.06663(15) -0.2461(2) 0.0286(4) Uani 1 1 d . . .
H15A H 0.075(2) 0.1419(17) -0.342(2) 0.028(5) Uiso 1 1 d . . .
H9 H -0.399(2) 0.2567(15) -0.7275(19) 0.017(4) Uiso 1 1 d . . .
H2C H -0.647(3) 0.1895(17) -1.091(3) 0.035(5) Uiso 1 1 d . . .
H16 H -0.121(2) 0.2953(17) -0.1479(19) 0.019(4) Uiso 1 1 d . . .
H7 H -0.041(3) 0.4653(15) -0.576(2) 0.027(5) Uiso 1 1 d . . .
H25B H -0.522(2) 0.1411(18) -0.267(2) 0.027(5) Uiso 1 1 d . . .
H25A H -0.544(2) 0.0279(16) -0.213(2) 0.025(5) Uiso 1 1 d . . .
H21 H -0.325(2) -0.0228(15) 0.034(2) 0.024(5) Uiso 1 1 d . . .
H14B H -0.463(2) 0.2304(13) -0.461(2) 0.017(4) Uiso 1 1 d . . .
H1A H -0.224(3) 0.5627(19) -1.069(2) 0.036(6) Uiso 1 1 d . . .
H12 H -0.182(2) 0.1810(15) -0.508(2) 0.016(4) Uiso 1 1 d . . .
H15B H 0.091(3) 0.2651(19) -0.330(2) 0.037(6) Uiso 1 1 d . . .
H2A H -0.510(2) 0.1515(17) -0.932(2) 0.032(5) Uiso 1 1 d . . .
H4C H 0.233(3) 0.2126(16) 0.511(3) 0.039(6) Uiso 1 1 d . . .
H1B H -0.263(3) 0.4936(17) -1.232(3) 0.043(6) Uiso 1 1 d . . .
H6 H -0.092(2) 0.5080(15) -0.833(2) 0.022(5) Uiso 1 1 d . . .
H3A H -0.309(3) -0.100(2) 0.250(3) 0.047(7) Uiso 1 1 d . . .
H25C H -0.560(3) 0.0470(17) -0.382(3) 0.039(6) Uiso 1 1 d . . .
H14A H -0.409(2) 0.2958(14) -0.298(2) 0.018(4) Uiso 1 1 d . . .
H24B H -0.185(3) -0.0780(15) -0.214(2) 0.025(5) Uiso 1 1 d . . .
H3B H -0.301(3) -0.0593(16) 0.405(3) 0.035(6) Uiso 1 1 d . . .
H4B H 0.240(2) 0.1993(16) 0.357(2) 0.031(5) Uiso 1 1 d . . .
H18 H 0.050(2) 0.2415(15) 0.132(2) 0.028(5) Uiso 1 1 d . . .
H4A H 0.137(3) 0.2935(19) 0.379(2) 0.033(5) Uiso 1 1 d . . .
H2B H -0.633(3) 0.2376(16) -0.930(2) 0.039(6) Uiso 1 1 d . . .
H1C H -0.110(3) 0.4772(16) -1.070(2) 0.034(6) Uiso 1 1 d . . .
H24A H -0.326(3) -0.1065(19) -0.168(3) 0.049(7) Uiso 1 1 d . . .
H24C H -0.359(3) -0.0867(18) -0.354(3) 0.044(6) Uiso 1 1 d . . .
H11 H -0.106(2) 0.3790(14) -0.399(2) 0.021(5) Uiso 1 1 d . . .
H3C H -0.398(4) -0.007(2) 0.249(3) 0.073(9) Uiso 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
O4 C19 1.372(2) . ?
O4 C4 1.422(2) . ?
O1 C5 1.364(2) . ?
O1 C1 1.432(2) . ?
O2 C10 1.367(2) . ?
O2 C2 1.426(2) . ?
O3 C20 1.369(2) . ?
O3 C3 1.428(3) . ?
O6 C13 1.419(2) . ?
O6 C23 1.453(2) . ?
O7 C16 1.435(2) . ?
O7 C15 1.438(2) . ?
C7 C8 1.375(3) . ?
C7 C6 1.405(3) . ?
C7 H7 1.01(2) . ?
C10 C9 1.383(2) . ?
C10 C5 1.410(3) . ?
O5 C14 1.429(2) . ?
O5 C11 1.447(2) . ?
C21 C20 1.384(2) . ?
C21 C22 1.406(2) . ?
C21 H21 0.96(2) . ?
C17 C22 1.385(2) . ?
C17 C18 1.400(2) . ?
C17 C16 1.493(2) . ?
C20 C19 1.403(3) . ?
C5 C6 1.380(3) . ?
C19 C18 1.373(2) . ?
C9 C8 1.405(3) . ?
C9 H9 0.95(2) . ?
C16 C13 1.527(2) . ?
C16 H16 0.99(2) . ?
C22 C23 1.517(2) . ?
C12 C13 1.524(2) . ?
C12 C15 1.530(3) . ?
C12 C11 1.537(2) . ?
C12 H12 0.944(19) . ?
C1 H1A 0.98(2) . ?
C1 H1B 1.04(2) . ?
C1 H1C 0.96(2) . ?
C11 C8 1.504(2) . ?
C11 H11 1.01(2) . ?
C2 H2C 0.99(2) . ?
C2 H2A 1.01(2) . ?
C2 H2B 0.99(2) . ?
C13 C14 1.531(3) . ?
C18 H18 1.02(2) . ?
C6 H6 1.01(2) . ?
C4 H4C 0.94(2) . ?
C4 H4B 0.94(2) . ?
C4 H4A 1.03(2) . ?
C15 H15A 1.02(2) . ?
C15 H15B 1.00(2) . ?
C3 H3A 0.92(3) . ?
C3 H3B 0.97(2) . ?
C3 H3C 0.95(3) . ?
C23 C25 1.523(3) . ?
C23 C24 1.526(3) . ?
C14 H14B 1.005(18) . ?
C14 H14A 0.997(18) . ?
C25 H25B 1.00(2) . ?
C25 H25A 1.00(2) . ?
C25 H25C 0.98(2) . ?
C24 H24B 1.01(2) . ?
C24 H24A 1.01(3) . ?
C24 H24C 1.00(2) . ?
 
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
C19 O4 C4 115.98(13) . . ?
C5 O1 C1 116.86(14) . . ?
C10 O2 C2 117.02(14) . . ?
C20 O3 C3 117.65(15) . . ?
C13 O6 C23 118.00(12) . . ?
C16 O7 C15 109.90(12) . . ?
C8 C7 C6 120.61(16) . . ?
C8 C7 H7 119.9(12) . . ?
C6 C7 H7 119.5(12) . . ?
O2 C10 C9 124.73(17) . . ?
O2 C10 C5 115.60(15) . . ?
C9 C10 C5 119.67(16) . . ?
C14 O5 C11 110.85(13) . . ?
C20 C21 C22 120.63(17) . . ?
C20 C21 H21 119.5(11) . . ?
C22 C21 H21 119.8(12) . . ?
C22 C17 C18 120.02(15) . . ?
C22 C17 C16 121.57(14) . . ?
C18 C17 C16 118.38(15) . . ?
O3 C20 C21 124.86(17) . . ?
O3 C20 C19 115.26(15) . . ?
C21 C20 C19 119.88(16) . . ?
O1 C5 C6 125.08(17) . . ?
O1 C5 C10 115.32(15) . . ?
C6 C5 C10 119.60(16) . . ?
O4 C19 C18 124.95(16) . . ?
O4 C19 C20 115.76(15) . . ?
C18 C19 C20 119.28(16) . . ?
C10 C9 C8 120.73(17) . . ?
C10 C9 H9 118.4(11) . . ?
C8 C9 H9 120.8(11) . . ?
O7 C16 C17 108.85(13) . . ?
O7 C16 C13 105.25(13) . . ?
C17 C16 C13 114.23(14) . . ?
O7 C16 H16 111.3(11) . . ?
C17 C16 H16 111.0(10) . . ?
C13 C16 H16 106.1(10) . . ?
C17 C22 C21 118.84(15) . . ?
C17 C22 C23 121.26(15) . . ?
C21 C22 C23 119.90(16) . . ?
C13 C12 C15 104.69(14) . . ?
C13 C12 C11 104.35(14) . . ?
C15 C12 C11 114.24(15) . . ?
C13 C12 H12 110.9(11) . . ?
C15 C12 H12 112.7(11) . . ?
C11 C12 H12 109.6(11) . . ?
O1 C1 H1A 110.9(13) . . ?
O1 C1 H1B 103.3(13) . . ?
H1A C1 H1B 116.7(18) . . ?
O1 C1 H1C 109.4(13) . . ?
H1A C1 H1C 105.1(18) . . ?
H1B C1 H1C 111.5(18) . . ?
O5 C11 C8 110.72(14) . . ?
O5 C11 C12 106.47(14) . . ?
C8 C11 C12 114.65(15) . . ?
O5 C11 H11 107.6(11) . . ?
C8 C11 H11 108.4(11) . . ?
C12 C11 H11 108.7(11) . . ?
O2 C2 H2C 103.5(13) . . ?
O2 C2 H2A 112.8(11) . . ?
H2C C2 H2A 110.4(17) . . ?
O2 C2 H2B 110.9(13) . . ?
H2C C2 H2B 111.7(18) . . ?
H2A C2 H2B 107.6(16) . . ?
O6 C13 C12 108.21(13) . . ?
O6 C13 C16 110.82(13) . . ?
C12 C13 C16 102.51(14) . . ?
O6 C13 C14 115.00(15) . . ?
C12 C13 C14 103.32(14) . . ?
C16 C13 C14 115.62(15) . . ?
C19 C18 C17 120.95(16) . . ?
C19 C18 H18 119.1(11) . . ?
C17 C18 H18 119.9(11) . . ?
C5 C6 C7 120.16(17) . . ?
C5 C6 H6 119.9(11) . . ?
C7 C6 H6 119.8(11) . . ?
C7 C8 C9 119.21(16) . . ?
C7 C8 C11 120.91(16) . . ?
C9 C8 C11 119.86(16) . . ?
O4 C4 H4C 102.5(13) . . ?
O4 C4 H4B 108.7(13) . . ?
H4C C4 H4B 107.8(18) . . ?
O4 C4 H4A 113.8(12) . . ?
H4C C4 H4A 112.0(18) . . ?
H4B C4 H4A 111.6(18) . . ?
O7 C15 C12 106.74(15) . . ?
O7 C15 H15A 106.0(11) . . ?
C12 C15 H15A 115.1(11) . . ?
O7 C15 H15B 110.5(13) . . ?
C12 C15 H15B 110.9(13) . . ?
H15A C15 H15B 107.5(16) . . ?
O3 C3 H3A 110.0(16) . . ?
O3 C3 H3B 107.6(13) . . ?
H3A C3 H3B 112(2) . . ?
O3 C3 H3C 111.9(18) . . ?
H3A C3 H3C 105(2) . . ?
H3B C3 H3C 111(2) . . ?
O6 C23 C22 111.24(14) . . ?
O6 C23 C25 110.65(14) . . ?
C22 C23 C25 111.80(15) . . ?
O6 C23 C24 102.06(13) . . ?
C22 C23 C24 110.67(15) . . ?
C25 C23 C24 110.03(16) . . ?
O5 C14 C13 106.57(14) . . ?
O5 C14 H14B 108.4(10) . . ?
C13 C14 H14B 107.5(10) . . ?
O5 C14 H14A 104.1(11) . . ?
C13 C14 H14A 114.9(11) . . ?
H14B C14 H14A 114.9(15) . . ?
C23 C25 H25B 111.3(11) . . ?
C23 C25 H25A 109.9(11) . . ?
H25B C25 H25A 108.6(16) . . ?
C23 C25 H25C 110.2(13) . . ?
H25B C25 H25C 109.0(17) . . ?
H25A C25 H25C 107.6(17) . . ?
C23 C24 H24B 107.9(11) . . ?
C23 C24 H24A 109.5(14) . . ?
H24B C24 H24A 102.8(18) . . ?
C23 C24 H24C 109.1(14) . . ?
H24B C24 H24C 110.7(17) . . ?
H24A C24 H24C 116.5(19) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              26.37
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.167
_refine_diff_density_min   -0.174
_refine_diff_density_rms    0.040
