 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H20 O6'
_chemical_formula_weight          380.38
 
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    Cc
_symmetry_space_group_name_hall  C-2yc
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    6.7778(3)
_cell_length_b                    20.1108(11)
_cell_length_c                    13.1963(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.674(2)
_cell_angle_gamma                 90.00
_cell_volume                      1786.56(18)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6884
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             'pale yellow'
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.414
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              800
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9797
_exptl_absorpt_correction_T_max   0.9898
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(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             5708
_diffrn_reflns_av_R_equivalents   0.0487
_diffrn_reflns_av_sigmaI/netI     0.0667
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -23
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.11
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2969
_reflns_number_gt                 2319
_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     'PLATON (Watkin, Pearce 1995)'
_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)+(0.0670P)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     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    2.0(13)
_refine_ls_number_reflns          2969
_refine_ls_number_parameters      257
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0731
_refine_ls_R_factor_gt            0.0503
_refine_ls_wR_factor_ref          0.1236
_refine_ls_wR_factor_gt           0.1136
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_restrained_S_all       1.043
_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
O1 O 0.6200(3) 0.20877(12) 0.88935(17) 0.0257(6) Uani 1 1 d . . .
O2 O 0.7631(3) 0.30630(11) 0.89954(18) 0.0302(6) Uani 1 1 d . . .
O3 O 0.5676(4) 0.41279(12) 0.9004(2) 0.0348(6) Uani 1 1 d . . .
H3O H 0.6691 0.3887 0.9020 0.052 Uiso 1 1 calc R . .
C1 C 0.4535(5) 0.16761(17) 0.8917(2) 0.0201(8) Uani 1 1 d . . .
C2 C 0.4932(6) 0.10017(17) 0.8964(2) 0.0270(10) Uani 1 1 d . . .
H2 H 0.6262 0.0845 0.9003 0.032 Uiso 1 1 calc R . .
C3 C 0.3384(5) 0.05605(18) 0.8952(3) 0.0306(9) Uani 1 1 d . . .
H3 H 0.3635 0.0096 0.8970 0.037 Uiso 1 1 calc R . .
C4 C 0.1446(6) 0.07961(18) 0.8915(3) 0.0301(10) Uani 1 1 d . . .
H4 H 0.0371 0.0492 0.8912 0.036 Uiso 1 1 calc R . .
C5 C 0.1087(5) 0.14719(19) 0.8882(3) 0.0274(8) Uani 1 1 d . . .
H5 H -0.0238 0.1628 0.8869 0.033 Uiso 1 1 calc R . .
C6 C 0.2638(6) 0.19330(18) 0.8869(2) 0.0219(9) Uani 1 1 d . . .
C7 C 0.2239(5) 0.26627(17) 0.8794(3) 0.0231(8) Uani 1 1 d . . .
H7A H 0.1409 0.2793 0.9331 0.028 Uiso 1 1 calc R . .
H7B H 0.1476 0.2760 0.8124 0.028 Uiso 1 1 calc R . .
C8 C 0.4113(6) 0.30749(16) 0.8907(2) 0.0197(8) Uani 1 1 d . . .
C9 C 0.4061(5) 0.37478(16) 0.8911(2) 0.0246(8) Uani 1 1 d . . .
C10 C 0.2177(5) 0.41427(17) 0.8793(3) 0.0304(9) Uani 1 1 d . . .
H10A H 0.2235 0.4483 0.9327 0.046 Uiso 1 1 calc R . .
H10B H 0.1049 0.3846 0.8853 0.046 Uiso 1 1 calc R . .
H10C H 0.2014 0.4357 0.8122 0.046 Uiso 1 1 calc R . .
C11 C 0.6044(5) 0.27650(18) 0.8944(2) 0.0236(8) Uani 1 1 d . . .
O4 O 0.3365(3) 0.16793(11) 0.62783(16) 0.0269(6) Uani 1 1 d . . .
O5 O 0.1981(3) 0.26613(12) 0.61888(17) 0.0294(6) Uani 1 1 d . . .
O6 O 0.3988(4) 0.37176(11) 0.6303(2) 0.0326(6) Uani 1 1 d . . .
H6 H 0.2957 0.3483 0.6222 0.049 Uiso 1 1 calc R . .
C12 C 0.5030(5) 0.12598(19) 0.6323(2) 0.0229(8) Uani 1 1 d . . .
C13 C 0.4600(5) 0.05904(16) 0.6237(3) 0.0276(8) Uani 1 1 d . . .
H13 H 0.3261 0.0441 0.6143 0.033 Uiso 1 1 calc R . .
C14 C 0.6154(6) 0.01384(18) 0.6289(3) 0.0308(9) Uani 1 1 d . . .
H14 H 0.5889 -0.0325 0.6227 0.037 Uiso 1 1 calc R . .
C15 C 0.8096(6) 0.03660(17) 0.6432(3) 0.0327(9) Uani 1 1 d . . .
H15 H 0.9164 0.0058 0.6480 0.039 Uiso 1 1 calc R . .
C16 C 0.8485(6) 0.10408(17) 0.6503(3) 0.0258(8) Uani 1 1 d . . .
H16 H 0.9823 0.1191 0.6594 0.031 Uiso 1 1 calc R . .
C17 C 0.6946(5) 0.15044(17) 0.6445(2) 0.0200(8) Uani 1 1 d . . .
C18 C 0.7371(5) 0.22352(18) 0.6544(3) 0.0209(8) Uani 1 1 d . . .
H18A H 0.8240 0.2368 0.6026 0.025 Uiso 1 1 calc R . .
H18B H 0.8094 0.2325 0.7226 0.025 Uiso 1 1 calc R . .
C19 C 0.5508(5) 0.26467(17) 0.6408(3) 0.0206(8) Uani 1 1 d . . .
C20 C 0.5586(5) 0.33244(18) 0.6419(3) 0.0228(9) Uani 1 1 d . . .
C21 C 0.7486(5) 0.37059(18) 0.6568(3) 0.0306(9) Uani 1 1 d . . .
H21A H 0.7991 0.3767 0.5908 0.046 Uiso 1 1 calc R . .
H21B H 0.8464 0.3460 0.7028 0.046 Uiso 1 1 calc R . .
H21C H 0.7249 0.4141 0.6865 0.046 Uiso 1 1 calc R . .
C22 C 0.3584(6) 0.23488(18) 0.6287(3) 0.0241(8) 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
O1 C11 1.369(4) . ?
O1 C1 1.403(4) . ?
O2 C11 1.226(4) . ?
O3 C9 1.329(4) . ?
O3 H3O 0.8400 . ?
C1 C6 1.380(5) . ?
C1 C2 1.383(5) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(4) . ?
C7 C8 1.509(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.354(4) . ?
C8 C11 1.446(5) . ?
C9 C10 1.496(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O4 C22 1.354(4) . ?
O4 C12 1.405(4) . ?
O5 C22 1.249(4) . ?
O6 C20 1.335(4) . ?
O6 H6 0.8400 . ?
C12 C13 1.379(5) . ?
C12 C17 1.380(5) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.500(5) . ?
C18 C19 1.503(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.364(4) . ?
C19 C22 1.427(5) . ?
C20 C21 1.492(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C11 O1 C1 121.3(3) . . ?
C9 O3 H3O 109.5 . . ?
C6 C1 C2 123.0(3) . . ?
C6 C1 O1 121.7(3) . . ?
C2 C1 O1 115.3(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 116.6(3) . . ?
C1 C6 C7 122.1(3) . . ?
C5 C6 C7 121.3(3) . . ?
C6 C7 C8 112.9(3) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C11 117.0(3) . . ?
C9 C8 C7 121.8(3) . . ?
C11 C8 C7 121.0(3) . . ?
O3 C9 C8 123.6(3) . . ?
O3 C9 C10 112.8(3) . . ?
C8 C9 C10 123.5(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 . . ?
O2 C11 O1 114.6(3) . . ?
O2 C11 C8 125.2(3) . . ?
O1 C11 C8 120.2(3) . . ?
C22 O4 C12 120.7(2) . . ?
C20 O6 H6 109.5 . . ?
C13 C12 C17 123.0(3) . . ?
C13 C12 O4 114.9(3) . . ?
C17 C12 O4 122.1(3) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 117.1(3) . . ?
C12 C17 C18 121.9(3) . . ?
C16 C17 C18 121.0(3) . . ?
C17 C18 C19 112.3(3) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C22 117.0(3) . . ?
C20 C19 C18 121.2(3) . . ?
C22 C19 C18 121.7(3) . . ?
O6 C20 C19 124.1(3) . . ?
O6 C20 C21 112.7(3) . . ?
C19 C20 C21 123.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 O4 114.0(3) . . ?
O5 C22 C19 125.0(3) . . ?
O4 C22 C19 121.1(3) . . ?
 
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
O6 H6 O5  0.84 1.78 2.518(3) 145.8 .
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.254
_refine_diff_density_min   -0.294
_refine_diff_density_rms    0.051
