 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H20 O6'
_chemical_formula_weight          356.36
 
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    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    13.4814(3)
_cell_length_b                    7.2705(2)
_cell_length_c                    17.7911(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.2660(10)
_cell_angle_gamma                 90.00
_cell_volume                      1738.99(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     26399
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       30.51
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.361
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              752
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.9753
_exptl_absorpt_correction_T_max   0.9802
_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             14074
_diffrn_reflns_av_R_equivalents   0.0408
_diffrn_reflns_av_sigmaI/netI     0.0328
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.03
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3064
_reflns_number_gt                 2597
_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)+(0.0488P)²+0.4576P] 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        0.0105(18)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3064
_refine_ls_number_parameters      316
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0432
_refine_ls_R_factor_gt            0.0349
_refine_ls_wR_factor_ref          0.0919
_refine_ls_wR_factor_gt           0.0870
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.041
_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
H5 H 0.5743(12) 0.753(2) 0.3717(9) 0.025(4) Uiso 1 1 d . . .
H19 H 0.7816(11) 1.266(2) 0.5049(9) 0.019(4) Uiso 1 1 d . . .
H18B H 0.7239(12) 1.303(2) 0.3491(9) 0.024(4) Uiso 1 1 d . . .
H16 H 0.9573(11) 1.436(2) 0.4241(8) 0.020(4) Uiso 1 1 d . . .
H3B H 0.7781(12) 0.929(2) 0.4794(8) 0.022(4) Uiso 1 1 d . . .
H9 H 0.8278(12) 0.920(2) 0.2173(9) 0.025(4) Uiso 1 1 d . . .
H7C H 0.3934(12) 0.631(2) 0.2295(9) 0.027(4) Uiso 1 1 d . . .
H3A H 0.6731(11) 0.835(2) 0.4809(8) 0.022(4) Uiso 1 1 d . . .
H20B H 0.6060(11) 1.465(2) 0.4530(9) 0.022(4) Uiso 1 1 d . . .
H18A H 0.7893(11) 1.461(2) 0.3911(8) 0.021(4) Uiso 1 1 d . . .
H7A H 0.4349(12) 0.794(2) 0.2854(9) 0.032(4) Uiso 1 1 d . . .
H2 H 0.6084(12) 1.131(2) 0.4242(9) 0.027(4) Uiso 1 1 d . . .
H12 H 0.9689(11) 0.836(2) 0.3303(8) 0.023(4) Uiso 1 1 d . . .
H20A H 0.6877(12) 1.531(2) 0.5214(9) 0.035(4) Uiso 1 1 d . . .
H7B H 0.4529(12) 0.585(2) 0.3109(10) 0.035(4) Uiso 1 1 d . . .
H14A H 1.1294(14) 0.828(2) 0.2778(11) 0.045(5) Uiso 1 1 d . . .
H14B H 1.2313(16) 0.797(3) 0.3282(11) 0.051(5) Uiso 1 1 d . . .
H14C H 1.1246(16) 0.705(3) 0.3572(12) 0.060(6) Uiso 1 1 d . . .
H4 H 0.6373(16) 0.676(3) 0.1328(11) 0.057(6) Uiso 1 1 d . . .
H6 H 1.1851(16) 1.270(3) 0.4051(11) 0.052(6) Uiso 1 1 d . . .
O3 O 0.53522(7) 0.66887(14) 0.22686(5) 0.0243(3) Uani 1 1 d . . .
O6 O 1.13432(8) 1.32727(15) 0.42196(6) 0.0270(3) Uani 1 1 d . . .
O2 O 0.57401(7) 1.02986(14) 0.57606(5) 0.0268(3) Uani 1 1 d . . .
O4 O 0.68567(7) 0.75923(14) 0.14293(5) 0.0236(3) Uani 1 1 d . . .
O1 O 0.60151(8) 1.32321(14) 0.54901(6) 0.0299(3) Uani 1 1 d . . .
O5 O 1.14855(7) 0.98259(15) 0.36924(6) 0.0304(3) Uani 1 1 d . . .
C5 C 0.62734(10) 0.78551(18) 0.34022(8) 0.0191(3) Uani 1 1 d . . .
C10 C 0.78464(10) 0.93499(18) 0.32683(7) 0.0196(3) Uani 1 1 d . . .
C9 C 0.77647(10) 0.88511(19) 0.25056(8) 0.0207(3) Uani 1 1 d . . .
C11 C 0.87388(10) 1.04309(19) 0.35554(7) 0.0208(3) Uani 1 1 d . . .
C12 C 0.96718(10) 0.9609(2) 0.34974(8) 0.0236(3) Uani 1 1 d . . .
C4 C 0.71021(10) 0.87929(18) 0.37251(7) 0.0185(3) Uani 1 1 d . . .
C6 C 0.61776(10) 0.74562(18) 0.26420(7) 0.0192(3) Uani 1 1 d . . .
C17 C 0.86917(10) 1.22276(19) 0.38373(7) 0.0205(3) Uani 1 1 d . . .
C8 C 0.69435(10) 0.79201(18) 0.21909(7) 0.0193(3) Uani 1 1 d . . .
C16 C 0.95829(10) 1.3129(2) 0.40597(8) 0.0221(3) Uani 1 1 d . . .
C3 C 0.71105(11) 0.92799(19) 0.45515(7) 0.0206(3) Uani 1 1 d . . .
C19 C 0.72712(10) 1.28402(19) 0.46554(8) 0.0217(3) Uani 1 1 d . . .
C13 C 1.05430(10) 1.0526(2) 0.37211(8) 0.0236(3) Uani 1 1 d . . .
C2 C 0.66169(10) 1.11370(19) 0.46489(7) 0.0202(3) Uani 1 1 d . . .
C18 C 0.77325(10) 1.3280(2) 0.39159(8) 0.0215(3) Uani 1 1 d . . .
C15 C 1.04960(10) 1.2311(2) 0.40040(7) 0.0220(3) Uani 1 1 d . . .
C1 C 0.60866(10) 1.14158(19) 0.53535(8) 0.0217(3) Uani 1 1 d . . .
C7 C 0.44682(11) 0.6703(2) 0.26687(9) 0.0255(3) Uani 1 1 d . . .
C20 C 0.65545(12) 1.4247(2) 0.49378(9) 0.0281(4) Uani 1 1 d . . .
C14 C 1.15851(13) 0.8149(3) 0.32905(11) 0.0421(5) 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
O3 C6 1.3714(16) . ?
O3 C7 1.4329(17) . ?
O6 C15 1.3693(17) . ?
O6 H6 0.87(2) . ?
O2 C1 1.2053(17) . ?
O4 C8 1.3723(16) . ?
O4 H4 0.90(2) . ?
O1 C1 1.3475(17) . ?
O1 C20 1.4647(18) . ?
O5 C13 1.3732(17) . ?
O5 C14 1.425(2) . ?
C5 C6 1.3798(19) . ?
C5 C4 1.3956(19) . ?
C5 H5 0.970(16) . ?
C10 C4 1.3974(19) . ?
C10 C9 1.4009(19) . ?
C10 C11 1.4949(19) . ?
C9 C8 1.3802(19) . ?
C9 H9 0.976(16) . ?
C11 C17 1.402(2) . ?
C11 C12 1.403(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.972(16) . ?
C4 C3 1.5115(18) . ?
C6 C8 1.3954(19) . ?
C17 C16 1.399(2) . ?
C17 C18 1.5178(19) . ?
C16 C15 1.377(2) . ?
C16 H16 0.954(16) . ?
C3 C2 1.5208(19) . ?
C3 H3B 0.972(16) . ?
C3 H3A 0.980(16) . ?
C19 C20 1.518(2) . ?
C19 C2 1.5199(19) . ?
C19 C18 1.5303(19) . ?
C19 H19 0.985(16) . ?
C13 C15 1.395(2) . ?
C2 C1 1.5023(19) . ?
C2 H2 0.990(16) . ?
C18 H18B 0.987(16) . ?
C18 H18A 0.988(16) . ?
C7 H7C 0.986(17) . ?
C7 H7A 0.978(18) . ?
C7 H7B 0.996(18) . ?
C20 H20B 0.991(16) . ?
C20 H20A 0.999(18) . ?
C14 H14A 0.97(2) . ?
C14 H14B 0.99(2) . ?
C14 H14C 1.06(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
C6 O3 C7 115.56(10) . . ?
C15 O6 H6 108.8(14) . . ?
C8 O4 H4 108.9(13) . . ?
C1 O1 C20 109.08(10) . . ?
C13 O5 C14 117.24(12) . . ?
C6 C5 C4 121.32(12) . . ?
C6 C5 H5 119.7(9) . . ?
C4 C5 H5 118.9(9) . . ?
C4 C10 C9 118.69(12) . . ?
C4 C10 C11 123.24(12) . . ?
C9 C10 C11 118.06(12) . . ?
C8 C9 C10 121.52(12) . . ?
C8 C9 H9 117.6(9) . . ?
C10 C9 H9 120.8(9) . . ?
C17 C11 C12 119.18(12) . . ?
C17 C11 C10 123.73(12) . . ?
C12 C11 C10 117.00(12) . . ?
C13 C12 C11 121.36(13) . . ?
C13 C12 H12 120.7(9) . . ?
C11 C12 H12 117.9(9) . . ?
C5 C4 C10 119.32(12) . . ?
C5 C4 C3 117.56(12) . . ?
C10 C4 C3 122.96(12) . . ?
O3 C6 C5 125.01(12) . . ?
O3 C6 C8 115.36(11) . . ?
C5 C6 C8 119.57(12) . . ?
C16 C17 C11 118.46(13) . . ?
C16 C17 C18 117.22(12) . . ?
C11 C17 C18 124.33(12) . . ?
O4 C8 C9 119.51(12) . . ?
O4 C8 C6 120.90(12) . . ?
C9 C8 C6 119.39(12) . . ?
C15 C16 C17 122.05(13) . . ?
C15 C16 H16 117.7(9) . . ?
C17 C16 H16 120.2(9) . . ?
C4 C3 C2 110.31(11) . . ?
C4 C3 H3B 111.9(8) . . ?
C2 C3 H3B 110.0(9) . . ?
C4 C3 H3A 109.1(8) . . ?
C2 C3 H3A 108.1(9) . . ?
H3B C3 H3A 107.4(12) . . ?
C20 C19 C2 99.69(11) . . ?
C20 C19 C18 116.95(12) . . ?
C2 C19 C18 115.86(11) . . ?
C20 C19 H19 108.4(8) . . ?
C2 C19 H19 107.3(8) . . ?
C18 C19 H19 108.0(9) . . ?
O5 C13 C12 125.39(13) . . ?
O5 C13 C15 115.16(12) . . ?
C12 C13 C15 119.45(13) . . ?
C1 C2 C19 101.28(11) . . ?
C1 C2 C3 117.02(11) . . ?
C19 C2 C3 117.75(12) . . ?
C1 C2 H2 103.2(9) . . ?
C19 C2 H2 106.8(9) . . ?
C3 C2 H2 109.4(9) . . ?
C17 C18 C19 112.18(12) . . ?
C17 C18 H18B 111.6(9) . . ?
C19 C18 H18B 109.0(9) . . ?
C17 C18 H18A 107.6(8) . . ?
C19 C18 H18A 108.3(8) . . ?
H18B C18 H18A 108.0(12) . . ?
O6 C15 C16 119.40(13) . . ?
O6 C15 C13 121.11(12) . . ?
C16 C15 C13 119.49(12) . . ?
O2 C1 O1 121.05(12) . . ?
O2 C1 C2 129.81(13) . . ?
O1 C1 C2 109.13(11) . . ?
O3 C7 H7C 104.9(9) . . ?
O3 C7 H7A 109.7(10) . . ?
H7C C7 H7A 111.5(13) . . ?
O3 C7 H7B 111.3(10) . . ?
H7C C7 H7B 111.3(13) . . ?
H7A C7 H7B 108.2(14) . . ?
O1 C20 C19 104.04(11) . . ?
O1 C20 H20B 107.3(9) . . ?
C19 C20 H20B 111.4(9) . . ?
O1 C20 H20A 106.2(9) . . ?
C19 C20 H20A 114.9(10) . . ?
H20B C20 H20A 112.3(13) . . ?
O5 C14 H14A 109.8(11) . . ?
O5 C14 H14B 104.4(11) . . ?
H14A C14 H14B 109.3(16) . . ?
O5 C14 H14C 110.2(11) . . ?
H14A C14 H14C 111.1(16) . . ?
H14B C14 H14C 111.8(16) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O4 H4 O2  0.90(2) 1.97(2) 2.7987(14) 153.8(19) 4_575
O4 H4 O3  0.90(2) 2.25(2) 2.6882(13) 110.1(16) .
O6 H6 O4  0.87(2) 2.00(2) 2.8078(14) 154.0(19) 2_755
O6 H6 O5  0.87(2) 2.23(2) 2.6876(15) 112.3(16) .
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.209
_refine_diff_density_min   -0.190
_refine_diff_density_rms    0.038
