 
data_s80
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H22 O6'
_chemical_formula_weight          370.39
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.270(5)
_cell_length_b                    8.870(4)
_cell_length_c                    13.050(9)
_cell_angle_alpha                 81.84(3)
_cell_angle_beta                  84.41(3)
_cell_angle_gamma                 78.71(1)
_cell_volume                      926.9(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              392
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             4396
_diffrn_reflns_av_R_equivalents   0.0494
_diffrn_reflns_av_sigmaI/netI     0.2479
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.67
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3801
_reflns_number_gt                 1145
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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+0.0000P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3801
_refine_ls_number_parameters      307
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0930
_refine_ls_R_factor_gt            0.0425
_refine_ls_wR_factor_ref          0.1216
_refine_ls_wR_factor_gt           0.0806
_refine_ls_goodness_of_fit_ref    0.446
_refine_ls_restrained_S_all       0.446
_refine_ls_shift/su_max           0.006
_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
O1 O 0.0696(3) 0.6730(3) 0.36517(18) 0.0619(6) Uani 1 1 d . . .
H1 H 0.0615 0.7628 0.3374 0.093 Uiso 1 1 calc R . .
O2 O -0.1086(3) 0.8255(2) 0.20975(18) 0.0612(6) Uani 1 1 d . . .
O3 O -0.4528(3) 0.2493(3) -0.04282(15) 0.0577(6) Uani 1 1 d . . .
O4 O -0.1863(3) 0.0407(3) 0.60982(18) 0.0689(7) Uani 1 1 d . . .
O5 O -0.7222(3) 0.1986(3) 0.06317(17) 0.0668(7) Uani 1 1 d . . .
O6 O -0.4600(3) 0.1179(2) 0.61944(15) 0.0556(6) Uani 1 1 d . . .
C1 C -0.0370(3) 0.6013(3) 0.3240(2) 0.0412(6) Uani 1 1 d . . .
C2 C -0.0538(3) 0.4531(3) 0.3668(2) 0.0396(6) Uani 1 1 d . . .
C3 C -0.1651(3) 0.3751(3) 0.33098(19) 0.0363(6) Uani 1 1 d . . .
C4 C -0.2607(3) 0.4509(3) 0.24910(19) 0.0358(6) Uani 1 1 d . . .
C5 C -0.2405(4) 0.6015(3) 0.2052(2) 0.0403(6) Uani 1 1 d . . .
C6 C -0.1318(4) 0.6765(3) 0.2430(2) 0.0421(6) Uani 1 1 d . . .
C7 C -0.2406(6) 0.9291(4) 0.1621(3) 0.0580(9) Uani 1 1 d . . .
C8 C -0.1836(4) 0.2179(3) 0.3890(2) 0.0409(6) Uani 1 1 d . . .
C9 C -0.3208(4) 0.2371(3) 0.4764(2) 0.0388(6) Uani 1 1 d . . .
C10 C -0.4955(4) 0.2391(3) 0.4491(2) 0.0405(6) Uani 1 1 d . . .
C11 C -0.5703(4) 0.3786(3) 0.3744(2) 0.0416(6) Uani 1 1 d . . .
C12 C -0.5289(3) 0.3500(3) 0.26194(19) 0.0375(6) Uani 1 1 d . . .
C13 C -0.3850(3) 0.3798(3) 0.20590(19) 0.0367(6) Uani 1 1 d . . .
C14 C -0.3067(4) 0.1201(3) 0.5727(2) 0.0468(7) Uani 1 1 d . . .
C15 C -0.5830(4) 0.2208(4) 0.5566(2) 0.0510(7) Uani 1 1 d . . .
C16 C -0.6435(4) 0.2882(3) 0.2159(2) 0.0429(6) Uani 1 1 d . . .
C17 C -0.6152(4) 0.2569(3) 0.1138(2) 0.0467(7) Uani 1 1 d . . .
C18 C -0.4702(4) 0.2868(3) 0.05610(19) 0.0414(6) Uani 1 1 d . . .
C19 C -0.3588(4) 0.3489(3) 0.1010(2) 0.0403(6) Uani 1 1 d . . .
C20 C -0.8753(5) 0.1785(7) 0.1176(3) 0.1090(19) Uani 1 1 d . . .
H20A H -0.8550 0.1113 0.1813 0.164 Uiso 1 1 calc R . .
H20B H -0.9373 0.1332 0.0757 0.164 Uiso 1 1 calc R . .
H20C H -0.9371 0.2773 0.1327 0.164 Uiso 1 1 calc R . .
C21 C -0.3072(5) 0.2739(5) -0.1045(2) 0.0722(11) Uani 1 1 d . . .
H21A H -0.3005 0.3818 -0.1120 0.108 Uiso 1 1 calc R . .
H21B H -0.3102 0.2428 -0.1717 0.108 Uiso 1 1 calc R . .
H21C H -0.2123 0.2138 -0.0716 0.108 Uiso 1 1 calc R . .
H2 H 0.012(4) 0.402(3) 0.427(2) 0.048(8) Uiso 1 1 d . . .
H5 H -0.311(3) 0.656(3) 0.1493(19) 0.032(6) Uiso 1 1 d . . .
H71 H -0.352(5) 0.937(4) 0.202(3) 0.086(13) Uiso 1 1 d . . .
H72 H -0.256(5) 0.906(5) 0.096(3) 0.092(13) Uiso 1 1 d . . .
H73 H -0.209(5) 1.033(5) 0.150(3) 0.085(12) Uiso 1 1 d . . .
H81 H -0.081(4) 0.172(3) 0.418(2) 0.041(7) Uiso 1 1 d . . .
H82 H -0.211(4) 0.148(3) 0.342(2) 0.045(8) Uiso 1 1 d . . .
H9 H -0.316(4) 0.338(3) 0.5008(19) 0.041(7) Uiso 1 1 d . . .
H10 H -0.493(4) 0.146(3) 0.413(2) 0.048(8) Uiso 1 1 d . . .
H111 H -0.528(4) 0.476(3) 0.3855(19) 0.039(7) Uiso 1 1 d . . .
H112 H -0.680(4) 0.394(3) 0.390(2) 0.049(8) Uiso 1 1 d . . .
H151 H -0.617(4) 0.321(4) 0.589(2) 0.055(9) Uiso 1 1 d . . .
H152 H -0.682(4) 0.175(4) 0.560(2) 0.057(9) Uiso 1 1 d . . .
H16 H -0.741(4) 0.260(4) 0.257(2) 0.055(9) Uiso 1 1 d . . .
H19 H -0.252(4) 0.376(3) 0.063(2) 0.047(8) 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
O1 C1 1.370(3) . ?
O1 H1 0.8200 . ?
O2 C6 1.375(3) . ?
O2 C7 1.414(4) . ?
O3 C18 1.366(3) . ?
O3 C21 1.417(4) . ?
O4 C14 1.202(4) . ?
O5 C17 1.370(3) . ?
O5 C20 1.421(4) . ?
O6 C14 1.355(4) . ?
O6 C15 1.459(4) . ?
C1 C2 1.382(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.404(4) . ?
C2 H2 1.00(3) . ?
C3 C4 1.405(3) . ?
C3 C8 1.517(4) . ?
C4 C5 1.412(4) . ?
C4 C13 1.497(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.99(3) . ?
C7 H71 1.01(4) . ?
C7 H72 0.94(4) . ?
C7 H73 0.99(4) . ?
C8 C9 1.531(4) . ?
C8 H81 0.95(3) . ?
C8 H82 1.00(3) . ?
C9 C14 1.511(4) . ?
C9 C10 1.518(4) . ?
C9 H9 1.00(3) . ?
C10 C15 1.517(4) . ?
C10 C11 1.530(4) . ?
C10 H10 1.00(3) . ?
C11 C12 1.519(4) . ?
C11 H111 1.03(3) . ?
C11 H112 0.90(3) . ?
C12 C13 1.386(4) . ?
C12 C16 1.402(4) . ?
C13 C19 1.422(4) . ?
C15 H151 1.02(3) . ?
C15 H152 0.98(3) . ?
C16 C17 1.389(4) . ?
C16 H16 0.98(3) . ?
C17 C18 1.402(4) . ?
C18 C19 1.375(4) . ?
C19 H19 1.03(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
 
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
C1 O1 H1 109.5 . . ?
C6 O2 C7 117.2(3) . . ?
C18 O3 C21 117.8(2) . . ?
C17 O5 C20 117.1(2) . . ?
C14 O6 C15 109.8(2) . . ?
O1 C1 C2 118.8(3) . . ?
O1 C1 C6 121.5(3) . . ?
C2 C1 C6 119.7(2) . . ?
C1 C2 C3 121.8(3) . . ?
C1 C2 H2 119.0(16) . . ?
C3 C2 H2 119.2(16) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 C8 117.4(2) . . ?
C4 C3 C8 124.0(2) . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C13 123.0(2) . . ?
C5 C4 C13 117.9(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.9(14) . . ?
C4 C5 H5 118.8(15) . . ?
O2 C6 C5 126.0(3) . . ?
O2 C6 C1 114.2(2) . . ?
C5 C6 C1 119.7(2) . . ?
O2 C7 H71 116(2) . . ?
O2 C7 H72 113(3) . . ?
H71 C7 H72 106(3) . . ?
O2 C7 H73 107(2) . . ?
H71 C7 H73 109(3) . . ?
H72 C7 H73 106(3) . . ?
C3 C8 C9 110.1(2) . . ?
C3 C8 H81 107.9(16) . . ?
C9 C8 H81 109.8(16) . . ?
C3 C8 H82 111.9(15) . . ?
C9 C8 H82 108.5(17) . . ?
H81 C8 H82 109(2) . . ?
C14 C9 C10 101.7(2) . . ?
C14 C9 C8 118.2(2) . . ?
C10 C9 C8 117.1(2) . . ?
C14 C9 H9 104.9(15) . . ?
C10 C9 H9 109.3(17) . . ?
C8 C9 H9 104.8(16) . . ?
C15 C10 C9 100.7(2) . . ?
C15 C10 C11 116.2(2) . . ?
C9 C10 C11 115.6(2) . . ?
C15 C10 H10 110.9(16) . . ?
C9 C10 H10 107.5(18) . . ?
C11 C10 H10 105.8(16) . . ?
C12 C11 C10 111.5(2) . . ?
C12 C11 H111 108.7(14) . . ?
C10 C11 H111 110.6(15) . . ?
C12 C11 H112 110.7(18) . . ?
C10 C11 H112 106.6(19) . . ?
H111 C11 H112 109(2) . . ?
C13 C12 C16 120.2(2) . . ?
C13 C12 C11 123.1(2) . . ?
C16 C12 C11 116.7(3) . . ?
C12 C13 C19 118.4(2) . . ?
C12 C13 C4 122.9(2) . . ?
C19 C13 C4 118.6(2) . . ?
O4 C14 O6 121.3(3) . . ?
O4 C14 C9 130.1(3) . . ?
O6 C14 C9 108.6(3) . . ?
O6 C15 C10 104.1(2) . . ?
O6 C15 H151 107.6(17) . . ?
C10 C15 H151 114.6(17) . . ?
O6 C15 H152 109.3(19) . . ?
C10 C15 H152 114.6(18) . . ?
H151 C15 H152 106(3) . . ?
C17 C16 C12 120.7(3) . . ?
C17 C16 H16 118.8(18) . . ?
C12 C16 H16 120.4(18) . . ?
O5 C17 C16 124.1(3) . . ?
O5 C17 C18 116.3(2) . . ?
C16 C17 C18 119.7(3) . . ?
O3 C18 C19 125.4(3) . . ?
O3 C18 C17 115.1(3) . . ?
C19 C18 C17 119.6(2) . . ?
C18 C19 C13 121.4(3) . . ?
C18 C19 H19 123.8(16) . . ?
C13 C19 H19 114.8(16) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.891
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.891
_refine_diff_density_max    0.171
_refine_diff_density_min   -0.224
_refine_diff_density_rms    0.054
