Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Prof Derek Boyd'
_publ_contact_author_address     
;
Department of Chemistry
Queens University
Belfast
BT9 5AG
;

_publ_contact_author_email       DR.BOYD@QUB.AC.UK

_publ_section_title              
;
Chemoenzymatic synthesis of carbasugars from iodobenzene
;
loop_
_publ_author_name
'D. Boyd'
'Christopher C. R. Allen'
'Nuria M. Llamas'
'John F. Malone'
C.R.O'Dowd
'Narain D. Sharma'

#===============================================================================

data_11
_database_code_depnum_ccdc_archive 'CCDC 262885'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Methyl 6,7-di(benzoyloxy)-2,2-dimethylperhydro-1,3-benzodioxole-4-carboxylate
;
_chemical_name_common            
;Methyl 6,7-di(benzoyloxy)-2,2-dimethylperhydro-1,3-
benzodioxole-4-carboxylate
;
_chemical_melting_point          156
_chemical_formula_moiety         'C25 H26 O8'
_chemical_formula_sum            'C25 H26 O8'
_chemical_formula_weight         454.46

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   P2(1)2(1)2(1)

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                   6.622(2)
_cell_length_b                   8.534(2)
_cell_length_c                   39.364(13)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2224.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.101
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3144
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2889
_reflns_number_gt                1108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97; enCIFer (CCDC, 2003)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1064P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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   3(2)
_refine_ls_number_reflns         2889
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2819
_refine_ls_R_factor_gt           0.0963
_refine_ls_wR_factor_ref         0.2600
_refine_ls_wR_factor_gt          0.1863
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002

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 0.0610(13) -0.0367(11) -0.1214(2) 0.024(2) Uani 1 1 d . . .
O2 O -0.0023(15) -0.1891(12) -0.1693(2) 0.031(3) Uani 1 1 d . . .
O3 O 0.1714(14) -0.4902(10) -0.1571(2) 0.023(2) Uani 1 1 d . . .
O4 O 0.5113(14) -0.4685(13) -0.1592(2) 0.042(3) Uani 1 1 d . . .
O5 O -0.0131(14) -0.5428(10) -0.0932(2) 0.022(2) Uani 1 1 d . . .
O6 O 0.1234(15) -0.6485(12) -0.0460(2) 0.041(3) Uani 1 1 d . . .
O7 O -0.3952(14) -0.3078(12) -0.0799(2) 0.031(3) Uani 1 1 d . . .
O8 O -0.2208(12) -0.3467(11) -0.0324(2) 0.025(3) Uani 1 1 d . . .
C1 C -0.0810(20) -0.1578(16) -0.1135(3) 0.024(4) Uani 1 1 d . . .
H1 H -0.2221 -0.1185 -0.1170 0.029 Uiso 1 1 calc R . .
C2 C -0.0320(20) -0.2830(17) -0.1396(3) 0.026(4) Uani 1 1 d . . .
H2 H -0.1486 -0.3561 -0.1427 0.031 Uiso 1 1 calc R . .
C3 C 0.1582(19) -0.3725(16) -0.1309(3) 0.018(3) Uani 1 1 d . . .
H3 H 0.2754 -0.2997 -0.1337 0.021 Uiso 1 1 calc R . .
C4 C 0.1630(20) -0.4366(16) -0.0951(3) 0.029(4) Uani 1 1 d . . .
H4 H 0.2918 -0.4951 -0.0908 0.035 Uiso 1 1 calc R . .
C5 C 0.1410(20) -0.3026(16) -0.0704(3) 0.027(4) Uani 1 1 d . . .
H5A H 0.2577 -0.2312 -0.0729 0.033 Uiso 1 1 calc R . .
H5B H 0.1423 -0.3444 -0.0470 0.033 Uiso 1 1 calc R . .
C6 C -0.0520(20) -0.2102(17) -0.0758(3) 0.025(4) Uani 1 1 d . . .
H6 H -0.0400 -0.1124 -0.0620 0.030 Uiso 1 1 calc R . .
C7 C 0.0620(20) -0.0323(18) -0.1578(3) 0.030(4) Uani 1 1 d . . .
C8 C -0.0910(20) 0.0844(17) -0.1704(4) 0.046(5) Uani 1 1 d . . .
H8A H -0.2249 0.0564 -0.1617 0.070 Uiso 1 1 calc R . .
H8B H -0.0929 0.0835 -0.1953 0.070 Uiso 1 1 calc R . .
H8C H -0.0544 0.1893 -0.1623 0.070 Uiso 1 1 calc R . .
C9 C 0.2740(20) 0.0001(17) -0.1707(3) 0.038(4) Uani 1 1 d . . .
H9A H 0.3090 0.1098 -0.1663 0.057 Uiso 1 1 calc R . .
H9B H 0.2799 -0.0203 -0.1952 0.057 Uiso 1 1 calc R . .
H9C H 0.3701 -0.0684 -0.1590 0.057 Uiso 1 1 calc R . .
C10 C 0.3600(20) -0.5147(17) -0.1718(3) 0.027(4) Uani 1 1 d . . .
C11 C 0.3430(20) -0.6039(15) -0.2041(3) 0.018(3) Uani 1 1 d . . .
C12 C 0.1600(20) -0.6147(17) -0.2222(3) 0.032(4) Uani 1 1 d . . .
H12 H 0.0401 -0.5690 -0.2132 0.038 Uiso 1 1 calc R . .
C13 C 0.1550(20) -0.6910(18) -0.2525(3) 0.032(4) Uani 1 1 d . . .
H13 H 0.0331 -0.6996 -0.2650 0.038 Uiso 1 1 calc R . .
C14 C 0.3321(30) -0.7555(16) -0.2646(3) 0.040(5) Uiso 1 1 d . . .
H14 H 0.3293 -0.8074 -0.2862 0.050 Uiso 1 1 calc R . .
C15 C 0.5131(30) -0.7481(20) -0.2474(4) 0.047(5) Uani 1 1 d . . .
H15 H 0.6304 -0.7971 -0.2561 0.057 Uiso 1 1 calc R . .
C16 C 0.5212(20) -0.6688(17) -0.2168(3) 0.033(4) Uani 1 1 d . . .
H16 H 0.6443 -0.6580 -0.2049 0.039 Uiso 1 1 calc R . .
C17 C -0.0082(20) -0.6467(17) -0.0656(3) 0.028(4) Uiso 1 1 d . . .
C18 C -0.2011(20) -0.7397(17) -0.0661(3) 0.030(4) Uani 1 1 d . . .
C19 C -0.2350(20) -0.8293(16) -0.0361(3) 0.030(4) Uani 1 1 d . . .
H19 H -0.1410 -0.8274 -0.0179 0.036 Uiso 1 1 calc R . .
C20 C -0.4080(20) -0.9194(19) -0.0341(4) 0.043(5) Uani 1 1 d . . .
H20 H -0.4311 -0.9830 -0.0146 0.051 Uiso 1 1 calc R . .
C21 C -0.5450(20) -0.9171(17) -0.0600(4) 0.036(4) Uani 1 1 d . . .
H21 H -0.6647 -0.9785 -0.0583 0.043 Uiso 1 1 calc R . .
C22 C -0.5130(20) -0.8263(17) -0.0885(3) 0.039(4) Uani 1 1 d . . .
H22 H -0.6109 -0.8266 -0.1061 0.047 Uiso 1 1 calc R . .
C23 C -0.3440(20) -0.7360(17) -0.0922(3) 0.031(4) Uani 1 1 d . . .
H23 H -0.3237 -0.6731 -0.1118 0.038 Uiso 1 1 calc R . .
C24 C -0.2430(20) -0.2926(16) -0.0640(3) 0.019(3) Uani 1 1 d . . .
C25 C -0.3960(20) -0.4219(18) -0.0176(3) 0.037(4) Uani 1 1 d . . .
H25A H -0.4951 -0.3420 -0.0109 0.056 Uiso 1 1 calc R . .
H25B H -0.3556 -0.4820 -0.0025 0.056 Uiso 1 1 calc R . .
H25C H -0.4574 -0.4926 -0.0343 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.026(6) 0.029(6) 0.018(4) -0.006(5) 0.006(4) -0.008(5)
O2 0.027(6) 0.052(7) 0.013(4) 0.012(5) -0.001(4) 0.015(7)
O3 0.028(5) 0.024(5) 0.015(4) -0.009(5) 0.004(5) -0.007(6)
O4 0.023(6) 0.067(9) 0.036(5) -0.025(6) -0.017(5) 0.013(7)
O5 0.025(6) 0.027(5) 0.016(4) -0.001(5) -0.002(4) 0.002(6)
O6 0.037(7) 0.050(7) 0.037(5) 0.012(6) -0.024(6) 0.005(7)
O7 0.020(5) 0.038(6) 0.035(5) 0.005(6) -0.005(5) -0.009(6)
O8 0.009(5) 0.045(7) 0.023(5) 0.004(5) -0.003(4) -0.004(5)
C1 0.025(8) 0.038(9) 0.009(6) 0.000(7) -0.002(6) -0.013(9)
C2 0.028(9) 0.037(9) 0.014(6) -0.005(7) 0.001(7) -0.009(9)
C3 0.030(6) 0.035(9) 0.019(6) -0.003(6) -0.006(6) -0.002(8)
C4 0.019(8) 0.028(9) 0.039(8) 0.000(7) -0.007(8) -0.012(9)
C5 0.023(9) 0.029(8) 0.028(7) -0.013(7) -0.007(7) 0.003(9)
C6 0.022(8) 0.029(9) 0.026(7) -0.003(7) -0.007(7) -0.012(8)
C7 0.041(10) 0.035(10) 0.016(7) -0.008(8) 0.008(7) -0.007(9)
C8 0.055(12) 0.034(10) 0.051(10) 0.017(9) -0.011(9) 0.003(10)
C9 0.048(11) 0.039(9) 0.029(8) 0.003(8) -0.003(8) -0.022(10)
C10 0.021(8) 0.034(9) 0.030(7) 0.013(8) 0.001(7) 0.019(9)
C11 0.039(9) 0.015(7) 0.002(5) 0.003(6) 0.005(7) -0.001(8)
C12 0.035(9) 0.037(10) 0.024(7) 0.001(8) 0.003(8) 0.006(10)
C13 0.030(9) 0.046(10) 0.021(7) -0.007(8) -0.007(7) 0.002(10)
C15 0.036(11) 0.065(13) 0.043(9) 0.006(9) -0.002(8) -0.009(11)
C16 0.041(10) 0.046(10) 0.012(6) -0.006(8) 0.014(7) -0.003(10)
C18 0.038(10) 0.038(9) 0.014(6) -0.007(7) -0.003(7) 0.006(9)
C19 0.046(10) 0.033(9) 0.013(6) -0.006(7) -0.006(7) 0.007(10)
C20 0.040(10) 0.041(11) 0.048(10) 0.007(9) 0.012(9) -0.005(11)
C21 0.028(9) 0.026(9) 0.056(10) -0.005(9) 0.028(8) -0.005(9)
C22 0.041(11) 0.046(10) 0.032(8) 0.011(9) 0.011(8) -0.016(11)
C23 0.040(10) 0.045(10) 0.010(6) 0.002(7) 0.010(7) -0.018(10)
C24 0.015(8) 0.024(9) 0.018(7) -0.006(7) 0.001(6) -0.003(8)
C25 0.024(9) 0.059(11) 0.026(7) 0.003(9) -0.003(7) 0.006(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 C7 1.436(13) . ?
O1 C1 1.433(14) . ?
O2 C2 1.431(14) . ?
O2 C7 1.474(16) . ?
O3 C10 1.392(15) . ?
O3 C3 1.442(14) . ?
O4 C10 1.184(15) . ?
O5 C17 1.403(15) . ?
O5 C4 1.481(15) . ?
O6 C17 1.161(15) . ?
O7 C24 1.195(14) . ?
O8 C24 1.337(15) . ?
O8 C25 1.450(14) . ?
C1 C2 1.519(16) . ?
C1 C6 1.561(16) . ?
C2 C3 1.513(17) . ?
C3 C4 1.514(15) . ?
C4 C5 1.506(17) . ?
C5 C6 1.518(18) . ?
C6 C24 1.516(17) . ?
C7 C8 1.503(19) . ?
C7 C9 1.520(17) . ?
C10 C11 1.487(16) . ?
C11 C16 1.392(18) . ?
C11 C12 1.411(19) . ?
C12 C13 1.360(17) . ?
C13 C14 1.38(2) . ?
C14 C15 1.38(2) . ?
C15 C16 1.375(19) . ?
C17 C18 1.503(19) . ?
C18 C23 1.398(18) . ?
C18 C19 1.421(18) . ?
C19 C20 1.381(18) . ?
C20 C21 1.368(19) . ?
C21 C22 1.380(17) . ?
C22 C23 1.368(19) . ?

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
C7 O1 C1 103.7(10) . . ?
C2 O2 C7 107.3(9) . . ?
C10 O3 C3 117.2(11) . . ?
C17 O5 C4 114.1(10) . . ?
C24 O8 C25 116.0(10) . . ?
O1 C1 C2 102.7(10) . . ?
O1 C1 C6 109.3(10) . . ?
C2 C1 C6 114.6(12) . . ?
O2 C2 C3 110.7(11) . . ?
O2 C2 C1 100.8(10) . . ?
C3 C2 C1 112.4(10) . . ?
O3 C3 C4 114.4(11) . . ?
O3 C3 C2 103.9(9) . . ?
C4 C3 C2 114.4(11) . . ?
O5 C4 C5 110.7(11) . . ?
O5 C4 C3 104.5(10) . . ?
C5 C4 C3 108.9(11) . . ?
C4 C5 C6 112.9(11) . . ?
C5 C6 C24 114.7(11) . . ?
C5 C6 C1 112.6(11) . . ?
C24 C6 C1 108.8(11) . . ?
O1 C7 O2 106.4(10) . . ?
O1 C7 C8 110.1(12) . . ?
O2 C7 C8 107.8(11) . . ?
O1 C7 C9 110.0(12) . . ?
O2 C7 C9 109.2(12) . . ?
C8 C7 C9 113.0(12) . . ?
O4 C10 O3 122.4(12) . . ?
O4 C10 C11 126.2(14) . . ?
O3 C10 C11 111.4(13) . . ?
C16 C11 C12 121.2(11) . . ?
C16 C11 C10 116.7(13) . . ?
C12 C11 C10 122.0(14) . . ?
C13 C12 C11 119.4(15) . . ?
C12 C13 C14 118.8(14) . . ?
C15 C14 C13 122.6(12) . . ?
C14 C15 C16 119.3(16) . . ?
C15 C16 C11 118.6(15) . . ?
O6 C17 O5 122.6(15) . . ?
O6 C17 C18 129.6(14) . . ?
O5 C17 C18 107.7(12) . . ?
C23 C18 C19 120.9(14) . . ?
C23 C18 C17 124.9(13) . . ?
C19 C18 C17 114.2(13) . . ?
C20 C19 C18 118.8(14) . . ?
C21 C20 C19 120.0(15) . . ?
C20 C21 C22 120.6(15) . . ?
C23 C22 C21 122.1(15) . . ?
C22 C23 C18 117.6(13) . . ?
O7 C24 O8 122.9(13) . . ?
O7 C24 C6 126.3(12) . . ?
O8 C24 C6 110.8(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C2 41.4(12) . . . . ?
C7 O1 C1 C6 163.4(12) . . . . ?
C7 O2 C2 C3 -92.8(13) . . . . ?
C7 O2 C2 C1 26.4(13) . . . . ?
O1 C1 C2 O2 -42.0(12) . . . . ?
C6 C1 C2 O2 -160.4(11) . . . . ?
O1 C1 C2 C3 75.9(12) . . . . ?
C6 C1 C2 C3 -42.5(16) . . . . ?
C10 O3 C3 C4 -98.8(13) . . . . ?
C10 O3 C3 C2 135.8(11) . . . . ?
O2 C2 C3 O3 -71.6(12) . . . . ?
C1 C2 C3 O3 176.5(10) . . . . ?
O2 C2 C3 C4 163.0(10) . . . . ?
C1 C2 C3 C4 51.0(15) . . . . ?
C17 O5 C4 C5 -79.1(12) . . . . ?
C17 O5 C4 C3 163.9(10) . . . . ?
O3 C3 C4 O5 -59.6(14) . . . . ?
C2 C3 C4 O5 60.1(13) . . . . ?
O3 C3 C4 C5 -177.9(11) . . . . ?
C2 C3 C4 C5 -58.2(16) . . . . ?
O5 C4 C5 C6 -56.4(14) . . . . ?
C3 C4 C5 C6 58.0(16) . . . . ?
C4 C5 C6 C24 73.7(14) . . . . ?
C4 C5 C6 C1 -51.3(15) . . . . ?
O1 C1 C6 C5 -71.5(14) . . . . ?
C2 C1 C6 C5 43.2(16) . . . . ?
O1 C1 C6 C24 160.3(10) . . . . ?
C2 C1 C6 C24 -85.1(14) . . . . ?
C1 O1 C7 O2 -25.1(13) . . . . ?
C1 O1 C7 C8 91.6(13) . . . . ?
C1 O1 C7 C9 -143.2(12) . . . . ?
C2 O2 C7 O1 -2.0(15) . . . . ?
C2 O2 C7 C8 -120.2(11) . . . . ?
C2 O2 C7 C9 116.7(12) . . . . ?
C3 O3 C10 O4 16.0(19) . . . . ?
C3 O3 C10 C11 -164.2(10) . . . . ?
O4 C10 C11 C16 15(2) . . . . ?
O3 C10 C11 C16 -164.8(11) . . . . ?
O4 C10 C11 C12 -161.1(15) . . . . ?
O3 C10 C11 C12 19.1(18) . . . . ?
C16 C11 C12 C13 1(2) . . . . ?
C10 C11 C12 C13 176.6(13) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C13 C14 C15 C16 -2(2) . . . . ?
C14 C15 C16 C11 3(2) . . . . ?
C12 C11 C16 C15 -2(2) . . . . ?
C10 C11 C16 C15 -178.1(13) . . . . ?
C4 O5 C17 O6 -0.2(17) . . . . ?
C4 O5 C17 C18 177.0(10) . . . . ?
O6 C17 C18 C23 -175.2(15) . . . . ?
O5 C17 C18 C23 7.9(18) . . . . ?
O6 C17 C18 C19 8(2) . . . . ?
O5 C17 C18 C19 -169.1(11) . . . . ?
C23 C18 C19 C20 3(2) . . . . ?
C17 C18 C19 C20 -179.8(12) . . . . ?
C18 C19 C20 C21 -2(2) . . . . ?
C19 C20 C21 C22 1(2) . . . . ?
C20 C21 C22 C23 0(2) . . . . ?
C21 C22 C23 C18 1(2) . . . . ?
C19 C18 C23 C22 -2(2) . . . . ?
C17 C18 C23 C22 -179.1(13) . . . . ?
C25 O8 C24 O7 -2(2) . . . . ?
C25 O8 C24 C6 177.3(11) . . . . ?
C5 C6 C24 O7 -131.0(15) . . . . ?
C1 C6 C24 O7 -4(2) . . . . ?
C5 C6 C24 O8 49.7(15) . . . . ?
C1 C6 C24 O8 176.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.063

#===END


#===============================================================================

data_32
_database_code_depnum_ccdc_archive 'CCDC 262886'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Methyl(1R,2S,3R,4R,5S)-2,3,4,5-tetra(acetyloxy)cyclohexane-1-carboxylate
;
_chemical_name_common            
;Methyl(1R,2S,3R,4R,5S)-2,3,4,5-tetra(acetyloxy)cyclohexane-1-
carboxylate
;
_chemical_melting_point          139
_chemical_formula_moiety         'C16 H22 O10'
_chemical_formula_sum            'C16 H22 O10'
_chemical_formula_weight         374.34

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   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.871(3)
_cell_length_b                   9.395(4)
_cell_length_c                   16.257(7)
_cell_angle_alpha                87.588(7)
_cell_angle_beta                 86.434(7)
_cell_angle_gamma                81.819(7)
_cell_volume                     885.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    662
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      22.90

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5440
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         23.26
_reflns_number_total             4751
_reflns_number_gt                2995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97; enCIFer (CCDC, 2003)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1064P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_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   3(2)
_refine_ls_number_reflns         4751
_refine_ls_number_parameters     479
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.003

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
C1A C 0.5050(17) 0.3285(9) 0.9582(6) 0.044(3) Uani 1 1 d . . .
H1A H 0.6615 0.3000 0.9310 0.053 Uiso 1 1 calc R . .
C2A C 0.3573(14) 0.4053(9) 0.8924(5) 0.031(2) Uani 1 1 d . . .
H2A H 0.1982 0.4373 0.9164 0.038 Uiso 1 1 calc R . .
C3A C 0.4624(14) 0.5335(9) 0.8564(6) 0.033(2) Uani 1 1 d . . .
H3A H 0.6082 0.5006 0.8232 0.040 Uiso 1 1 calc R . .
C4A C 0.5081(13) 0.6333(9) 0.9216(6) 0.032(2) Uani 1 1 d . . .
H4A H 0.3596 0.6837 0.9463 0.038 Uiso 1 1 calc R . .
C5A C 0.6446(15) 0.5522(9) 0.9867(6) 0.033(2) Uani 1 1 d . . .
H5A H 0.8033 0.5164 0.9636 0.040 Uiso 1 1 calc R . .
C6A C 0.5342(16) 0.4301(10) 1.0238(6) 0.046(3) Uani 1 1 d . . .
H6A1 H 0.3819 0.4667 1.0504 0.055 Uiso 1 1 calc R . .
H6A2 H 0.6312 0.3793 1.0666 0.055 Uiso 1 1 calc R . .
C7A C 0.430(2) 0.1886(13) 1.0005(7) 0.064(3) Uani 1 1 d . . .
O7A O 0.5648(12) 0.0959(7) 1.0292(5) 0.064(2) Uani 1 1 d . . .
O8A O 0.2238(13) 0.2081(8) 1.0014(4) 0.069(2) Uani 1 1 d . . .
C8A C 0.143(2) 0.0673(12) 1.0473(7) 0.088(4) Uani 1 1 d . . .
H8A1 H 0.2010 -0.0175 1.0151 0.132 Uiso 1 1 calc R . .
H8A2 H -0.0262 0.0784 1.0524 0.132 Uiso 1 1 calc R . .
H8A3 H 0.2034 0.0551 1.1023 0.132 Uiso 1 1 calc R . .
O2A O 0.3492(9) 0.3086(6) 0.8290(4) 0.0330(15) Uani 1 1 d . . .
C9A C 0.1439(14) 0.2849(9) 0.8060(6) 0.032(2) Uani 1 1 d . . .
O9A O -0.0295(10) 0.3396(7) 0.8353(4) 0.0479(18) Uani 1 1 d . . .
C10A C 0.1690(16) 0.1743(10) 0.7410(6) 0.044(3) Uani 1 1 d . . .
H10D H 0.0172 0.1667 0.7210 0.066 Uiso 1 1 calc R . .
H10E H 0.2357 0.0810 0.7644 0.066 Uiso 1 1 calc R . .
H10F H 0.2704 0.2032 0.6950 0.066 Uiso 1 1 calc R . .
O3A O 0.2922(9) 0.6074(6) 0.8036(4) 0.0348(15) Uani 1 1 d . . .
C11A C 0.3634(16) 0.6661(10) 0.7335(5) 0.036(2) Uani 1 1 d . . .
O11A O 0.5597(11) 0.6632(7) 0.7116(4) 0.0461(18) Uani 1 1 d . . .
C12A C 0.1699(14) 0.7437(10) 0.6889(5) 0.042(3) Uani 1 1 d . . .
H12D H 0.1100 0.8329 0.7169 0.063 Uiso 1 1 calc R . .
H12E H 0.0474 0.6831 0.6880 0.063 Uiso 1 1 calc R . .
H12F H 0.2235 0.7668 0.6323 0.063 Uiso 1 1 calc R . .
O4A O 0.6444(8) 0.7337(6) 0.8866(3) 0.0310(15) Uani 1 1 d . . .
C13A C 0.5482(17) 0.8696(10) 0.8686(6) 0.036(2) Uani 1 1 d . . .
O13A O 0.3460(11) 0.9048(7) 0.8767(5) 0.053(2) Uani 1 1 d . . .
C14A C 0.7215(16) 0.9558(10) 0.8385(6) 0.047(3) Uani 1 1 d . . .
H14D H 0.7873 0.9219 0.7848 0.070 Uiso 1 1 calc R . .
H14E H 0.8436 0.9478 0.8776 0.070 Uiso 1 1 calc R . .
H14F H 0.6517 1.0566 0.8327 0.070 Uiso 1 1 calc R . .
O5A O 0.6564(10) 0.6554(7) 1.0506(4) 0.053(2) Uani 1 1 d . . .
C15A C 0.8607(15) 0.6807(9) 1.0676(6) 0.034(2) Uani 1 1 d . . .
O15A O 1.0299(13) 0.6202(8) 1.0418(5) 0.082(2) Uani 1 1 d . . .
C16A C 0.8517(18) 0.7894(10) 1.1286(6) 0.058(3) Uani 1 1 d . . .
H16D H 0.8155 0.7477 1.1833 0.088 Uiso 1 1 calc R . .
H16E H 0.7322 0.8697 1.1158 0.088 Uiso 1 1 calc R . .
H16F H 1.0014 0.8242 1.1281 0.088 Uiso 1 1 calc R . .
C1B C 0.2428(14) 0.5589(10) 0.3291(5) 0.033(2) Uani 1 1 d . . .
H1B H 0.0902 0.6060 0.3523 0.039 Uiso 1 1 calc R . .
C2B C 0.3716(14) 0.4751(9) 0.3968(5) 0.028(2) Uani 1 1 d . . .
H2B H 0.5201 0.4227 0.3734 0.033 Uiso 1 1 calc R . .
C3B C 0.4177(13) 0.5692(8) 0.4633(5) 0.023(2) Uani 1 1 d . . .
H3B H 0.2716 0.6062 0.4952 0.028 Uiso 1 1 calc R . .
C4B C 0.5360(14) 0.6899(9) 0.4289(6) 0.030(2) Uani 1 1 d . . .
H4B H 0.6979 0.6521 0.4101 0.036 Uiso 1 1 calc R . .
C5B C 0.4172(13) 0.7712(9) 0.3590(5) 0.030(2) Uani 1 1 d . . .
H5B H 0.2663 0.8247 0.3796 0.036 Uiso 1 1 calc R . .
C6B C 0.3793(14) 0.6726(9) 0.2920(5) 0.031(2) Uani 1 1 d . . .
H6B1 H 0.5294 0.6269 0.2678 0.037 Uiso 1 1 calc R . .
H6B2 H 0.2939 0.7281 0.2478 0.037 Uiso 1 1 calc R . .
C7B C 0.2060(15) 0.4612(9) 0.2640(6) 0.030(2) Uani 1 1 d . . .
O7B O 0.3582(8) 0.3911(6) 0.2246(3) 0.0396(14) Uani 1 1 d . . .
O8B O -0.0139(10) 0.4585(6) 0.2537(4) 0.0426(17) Uani 1 1 d . . .
C8B C -0.0554(17) 0.3557(11) 0.1945(6) 0.054(3) Uani 1 1 d . . .
H8B1 H 0.0236 0.3763 0.1414 0.082 Uiso 1 1 calc R . .
H8B2 H -0.2214 0.3628 0.1877 0.082 Uiso 1 1 calc R . .
H8B3 H 0.0034 0.2582 0.2143 0.082 Uiso 1 1 calc R . .
O2B O 0.2223(9) 0.3730(6) 0.4281(3) 0.0337(16) Uani 1 1 d . . .
C9B C 0.3154(17) 0.2405(10) 0.4479(5) 0.035(2) Uani 1 1 d . . .
O9B O 0.5160(11) 0.1991(7) 0.4452(4) 0.0486(19) Uani 1 1 d . . .
C10B C 0.1361(15) 0.1477(10) 0.4743(7) 0.053(3) Uani 1 1 d . . .
H10A H 0.1666 0.0575 0.4449 0.079 Uiso 1 1 calc R . .
H10B H -0.0163 0.1980 0.4616 0.079 Uiso 1 1 calc R . .
H10C H 0.1400 0.1268 0.5338 0.079 Uiso 1 1 calc R . .
O3B O 0.5812(8) 0.4912(6) 0.5168(4) 0.0302(14) Uani 1 1 d . . .
C11B C 0.5023(16) 0.4318(9) 0.5884(6) 0.035(2) Uani 1 1 d . . .
O11B O 0.3006(10) 0.4372(7) 0.6083(4) 0.0404(16) Uani 1 1 d . . .
C12B C 0.6985(15) 0.3575(11) 0.6335(7) 0.052(3) Uani 1 1 d . . .
H12A H 0.6609 0.3625 0.6929 0.078 Uiso 1 1 calc R . .
H12B H 0.8355 0.4041 0.6192 0.078 Uiso 1 1 calc R . .
H12C H 0.7293 0.2565 0.6181 0.078 Uiso 1 1 calc R . .
O4B O 0.5387(8) 0.7881(6) 0.4946(4) 0.0313(15) Uani 1 1 d . . .
C13B C 0.7450(16) 0.8269(10) 0.5121(6) 0.037(2) Uani 1 1 d . . .
O13B O 0.9238(9) 0.7787(7) 0.4791(4) 0.0437(18) Uani 1 1 d . . .
C14B C 0.7023(14) 0.9290(9) 0.5784(6) 0.038(2) Uani 1 1 d . . .
H14A H 0.8452 0.9669 0.5879 0.057 Uiso 1 1 calc R . .
H14B H 0.6490 0.8803 0.6289 0.057 Uiso 1 1 calc R . .
H14C H 0.5842 1.0084 0.5628 0.057 Uiso 1 1 calc R . .
O5B O 0.5666(10) 0.8700(6) 0.3286(4) 0.0406(16) Uani 1 1 d . . .
C15B C 0.4796(15) 0.9900(9) 0.2870(5) 0.039(2) Uani 1 1 d . . .
O15B O 0.2783(11) 1.0134(7) 0.2785(5) 0.056(2) Uani 1 1 d . . .
C16B C 0.6533(16) 1.0765(9) 0.2577(6) 0.058(3) Uani 1 1 d . . .
H16A H 0.6433 1.0957 0.1982 0.087 Uiso 1 1 calc R . .
H16B H 0.8061 1.0250 0.2687 0.087 Uiso 1 1 calc R . .
H16C H 0.6288 1.1678 0.2861 0.087 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.065(6) 0.034(6) 0.032(6) 0.018(5) -0.005(5) -0.010(5)
C2A 0.038(5) 0.038(5) 0.022(5) -0.014(5) 0.003(4) -0.016(4)
C3A 0.030(5) 0.036(6) 0.032(6) 0.008(5) -0.008(4) -0.002(4)
C4A 0.018(4) 0.036(5) 0.041(6) 0.000(5) 0.005(4) -0.006(4)
C5A 0.041(5) 0.027(5) 0.035(6) -0.009(5) -0.011(4) -0.015(4)
C6A 0.060(6) 0.053(7) 0.021(6) 0.001(5) 0.002(4) -0.004(5)
C7A 0.062(8) 0.074(9) 0.058(8) -0.025(6) -0.007(6) -0.010(7)
O7A 0.062(5) 0.045(5) 0.083(6) 0.028(4) -0.007(4) -0.007(4)
O8A 0.064(5) 0.081(6) 0.055(5) -0.009(4) -0.005(4) 0.014(4)
C8A 0.116(10) 0.080(9) 0.078(9) 0.013(7) 0.039(8) -0.069(8)
O2A 0.026(3) 0.039(4) 0.034(4) -0.001(3) 0.011(3) -0.010(3)
C9A 0.024(5) 0.029(5) 0.043(6) 0.014(5) -0.001(5) -0.006(4)
O9A 0.031(4) 0.064(5) 0.047(4) -0.005(4) 0.001(3) -0.005(3)
C10A 0.057(6) 0.039(6) 0.037(6) 0.010(5) -0.017(5) -0.002(5)
O3A 0.032(3) 0.045(4) 0.026(4) -0.005(3) -0.001(3) 0.001(3)
C11A 0.044(6) 0.050(6) 0.010(5) -0.006(4) 0.005(5) 0.004(5)
O11A 0.048(4) 0.056(4) 0.032(4) 0.008(3) 0.003(3) -0.005(3)
C12A 0.049(6) 0.051(7) 0.022(5) -0.007(5) -0.010(5) 0.010(5)
O4A 0.027(3) 0.032(4) 0.034(4) 0.002(3) 0.006(3) -0.007(3)
C13A 0.051(6) 0.023(6) 0.036(6) 0.005(5) -0.004(5) -0.011(5)
O13A 0.045(4) 0.044(4) 0.070(6) 0.003(4) -0.004(4) -0.005(4)
C14A 0.063(7) 0.039(6) 0.040(6) 0.008(5) 0.002(5) -0.015(5)
O5A 0.044(4) 0.066(5) 0.052(5) 0.005(4) -0.007(3) -0.023(4)
C15A 0.021(5) 0.034(5) 0.042(6) 0.003(4) 0.020(4) -0.003(4)
O15A 0.068(5) 0.084(5) 0.101(6) -0.027(5) 0.002(4) -0.025(4)
C16A 0.101(9) 0.038(6) 0.047(6) -0.004(5) -0.011(6) -0.043(6)
C1B 0.037(5) 0.038(6) 0.021(5) 0.001(4) 0.003(4) 0.000(4)
C2B 0.036(5) 0.025(5) 0.021(5) 0.003(4) 0.007(4) -0.007(4)
C3B 0.023(4) 0.029(5) 0.016(5) 0.004(4) 0.007(4) -0.002(4)
C4B 0.031(5) 0.029(5) 0.029(5) -0.003(4) 0.005(4) -0.002(4)
C5B 0.030(4) 0.024(5) 0.039(6) -0.005(4) 0.012(4) -0.018(4)
C6B 0.038(5) 0.036(5) 0.021(5) 0.000(4) 0.004(4) -0.016(4)
C7B 0.036(5) 0.026(5) 0.027(6) 0.004(4) -0.003(4) -0.003(4)
O7B 0.036(3) 0.052(4) 0.030(3) -0.012(3) 0.008(2) -0.006(3)
O8B 0.041(4) 0.050(4) 0.039(4) 0.003(3) -0.011(3) -0.012(3)
C8B 0.067(6) 0.051(6) 0.051(6) -0.017(5) -0.007(5) -0.021(5)
O2B 0.032(3) 0.033(4) 0.038(4) -0.001(3) 0.006(3) -0.011(3)
C9B 0.049(6) 0.030(6) 0.023(6) 0.003(4) 0.007(5) -0.004(5)
O9B 0.046(4) 0.040(4) 0.057(5) 0.011(4) 0.002(4) 0.002(3)
C10B 0.056(6) 0.035(6) 0.069(8) -0.007(6) 0.018(6) -0.020(5)
O3B 0.028(3) 0.028(3) 0.034(4) 0.006(3) 0.000(3) -0.003(2)
C11B 0.040(6) 0.021(5) 0.043(7) 0.000(5) -0.004(5) -0.004(4)
O11B 0.041(4) 0.045(4) 0.037(4) 0.014(3) 0.000(3) -0.017(3)
C12B 0.046(6) 0.054(7) 0.052(7) 0.003(6) -0.004(5) 0.004(5)
O4B 0.029(3) 0.029(3) 0.036(4) -0.003(3) 0.000(3) -0.004(3)
C13B 0.046(6) 0.035(6) 0.031(6) 0.013(5) -0.007(5) -0.017(5)
O13B 0.025(3) 0.049(4) 0.058(5) -0.002(4) 0.002(3) -0.009(3)
C14B 0.042(5) 0.031(5) 0.047(7) -0.006(5) -0.003(5) -0.021(4)
O5B 0.044(4) 0.038(4) 0.039(4) 0.004(3) -0.001(3) -0.004(3)
C15B 0.044(6) 0.033(5) 0.037(5) 0.013(4) 0.003(4) -0.004(4)
O15B 0.039(4) 0.051(5) 0.075(5) 0.025(4) -0.001(3) -0.002(3)
C16B 0.075(7) 0.038(6) 0.061(7) -0.002(5) 0.028(5) -0.022(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
C1A C6A 1.495(13) . ?
C1A C2A 1.512(12) . ?
C1A C7A 1.565(14) . ?
C2A O2A 1.410(10) . ?
C2A C3A 1.511(12) . ?
C3A O3A 1.441(10) . ?
C3A C4A 1.505(13) . ?
C4A O4A 1.403(10) . ?
C4A C5A 1.485(12) . ?
C5A O5A 1.463(11) . ?
C5A C6A 1.485(12) . ?
C7A O7A 1.192(12) . ?
C7A O8A 1.195(11) . ?
O8A C8A 1.608(11) . ?
O2A C9A 1.335(10) . ?
C9A O9A 1.157(9) . ?
C9A C10A 1.499(12) . ?
O3A C11A 1.316(10) . ?
C11A O11A 1.182(10) . ?
C11A C12A 1.473(11) . ?
O4A C13A 1.348(10) . ?
C13A O13A 1.187(10) . ?
C13A C14A 1.439(13) . ?
O5A C15A 1.303(10) . ?
C15A O15A 1.137(10) . ?
C15A C16A 1.447(12) . ?
C1B C7B 1.475(12) . ?
C1B C2B 1.504(12) . ?
C1B C6B 1.509(12) . ?
C2B O2B 1.445(9) . ?
C2B C3B 1.487(11) . ?
C3B O3B 1.436(9) . ?
C3B C4B 1.485(11) . ?
C4B O4B 1.443(10) . ?
C4B C5B 1.495(12) . ?
C5B O5B 1.419(9) . ?
C5B C6B 1.506(12) . ?
C7B O7B 1.201(9) . ?
C7B O8B 1.316(10) . ?
O8B C8B 1.447(10) . ?
O2B C9B 1.322(11) . ?
C9B O9B 1.185(10) . ?
C9B C10B 1.492(12) . ?
O3B C11B 1.354(11) . ?
C11B O11B 1.203(10) . ?
C11B C12B 1.478(12) . ?
O4B C13B 1.363(11) . ?
C13B O13B 1.187(10) . ?
C13B C14B 1.458(12) . ?
O5B C15B 1.344(9) . ?
C15B O15B 1.186(10) . ?
C15B C16B 1.439(11) . ?

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
C6A C1A C2A 110.2(8) . . ?
C6A C1A C7A 108.5(8) . . ?
C2A C1A C7A 118.0(8) . . ?
O2A C2A C3A 108.5(7) . . ?
O2A C2A C1A 108.1(7) . . ?
C3A C2A C1A 110.3(7) . . ?
O3A C3A C4A 109.3(7) . . ?
O3A C3A C2A 104.8(7) . . ?
C4A C3A C2A 112.3(8) . . ?
O4A C4A C5A 106.0(6) . . ?
O4A C4A C3A 109.4(7) . . ?
C5A C4A C3A 110.4(7) . . ?
O5A C5A C4A 105.7(7) . . ?
O5A C5A C6A 108.7(7) . . ?
C4A C5A C6A 112.6(7) . . ?
C5A C6A C1A 109.5(8) . . ?
O7A C7A O8A 133.1(12) . . ?
O7A C7A C1A 122.1(10) . . ?
O8A C7A C1A 104.5(10) . . ?
C7A O8A C8A 105.3(9) . . ?
C9A O2A C2A 118.7(7) . . ?
O9A C9A O2A 123.6(9) . . ?
O9A C9A C10A 125.1(9) . . ?
O2A C9A C10A 111.2(8) . . ?
C11A O3A C3A 118.4(6) . . ?
O11A C11A O3A 123.7(8) . . ?
O11A C11A C12A 124.4(8) . . ?
O3A C11A C12A 111.7(8) . . ?
C13A O4A C4A 120.2(7) . . ?
O13A C13A O4A 121.3(8) . . ?
O13A C13A C14A 128.0(9) . . ?
O4A C13A C14A 110.7(8) . . ?
C15A O5A C5A 117.1(7) . . ?
O15A C15A O5A 125.1(10) . . ?
O15A C15A C16A 122.3(9) . . ?
O5A C15A C16A 112.4(8) . . ?
C7B C1B C2B 109.8(7) . . ?
C7B C1B C6B 109.0(7) . . ?
C2B C1B C6B 110.0(7) . . ?
O2B C2B C3B 110.6(6) . . ?
O2B C2B C1B 104.6(6) . . ?
C3B C2B C1B 112.0(7) . . ?
O3B C3B C2B 109.8(7) . . ?
O3B C3B C4B 103.7(6) . . ?
C2B C3B C4B 110.8(7) . . ?
O4B C4B C3B 107.1(7) . . ?
O4B C4B C5B 108.0(7) . . ?
C3B C4B C5B 113.5(7) . . ?
O5B C5B C4B 105.4(6) . . ?
O5B C5B C6B 110.2(7) . . ?
C4B C5B C6B 111.5(7) . . ?
C5B C6B C1B 108.6(7) . . ?
O7B C7B O8B 123.1(8) . . ?
O7B C7B C1B 124.3(8) . . ?
O8B C7B C1B 112.6(8) . . ?
C7B O8B C8B 113.8(7) . . ?
C9B O2B C2B 118.8(7) . . ?
O9B C9B O2B 124.8(9) . . ?
O9B C9B C10B 123.6(9) . . ?
O2B C9B C10B 111.6(8) . . ?
C11B O3B C3B 118.8(6) . . ?
O11B C11B O3B 123.1(8) . . ?
O11B C11B C12B 127.1(9) . . ?
O3B C11B C12B 109.7(8) . . ?
C13B O4B C4B 118.2(7) . . ?
O13B C13B O4B 123.5(9) . . ?
O13B C13B C14B 128.6(9) . . ?
O4B C13B C14B 107.9(8) . . ?
C15B O5B C5B 119.4(7) . . ?
O15B C15B O5B 119.3(8) . . ?
O15B C15B C16B 127.9(9) . . ?
O5B C15B C16B 112.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A O2A 175.6(7) . . . . ?
C7A C1A C2A O2A -59.1(10) . . . . ?
C6A C1A C2A C3A 57.1(10) . . . . ?
C7A C1A C2A C3A -177.6(8) . . . . ?
O2A C2A C3A O3A 69.3(9) . . . . ?
C1A C2A C3A O3A -172.4(7) . . . . ?
O2A C2A C3A C4A -172.2(7) . . . . ?
C1A C2A C3A C4A -53.9(10) . . . . ?
O3A C3A C4A O4A -75.5(8) . . . . ?
C2A C3A C4A O4A 168.7(7) . . . . ?
O3A C3A C4A C5A 168.3(6) . . . . ?
C2A C3A C4A C5A 52.5(9) . . . . ?
O4A C4A C5A O5A 67.8(8) . . . . ?
C3A C4A C5A O5A -173.8(7) . . . . ?
O4A C4A C5A C6A -173.7(7) . . . . ?
C3A C4A C5A C6A -55.4(10) . . . . ?
O5A C5A C6A C1A 176.0(8) . . . . ?
C4A C5A C6A C1A 59.2(10) . . . . ?
C2A C1A C6A C5A -59.3(10) . . . . ?
C7A C1A C6A C5A 170.1(8) . . . . ?
C6A C1A C7A O7A -80.9(12) . . . . ?
C2A C1A C7A O7A 152.9(9) . . . . ?
C6A C1A C7A O8A 93.7(10) . . . . ?
C2A C1A C7A O8A -32.5(12) . . . . ?
O7A C7A O8A C8A -4.6(16) . . . . ?
C1A C7A O8A C8A -178.3(7) . . . . ?
C3A C2A O2A C9A -114.5(8) . . . . ?
C1A C2A O2A C9A 125.8(8) . . . . ?
C2A O2A C9A O9A 0.1(13) . . . . ?
C2A O2A C9A C10A -177.3(7) . . . . ?
C4A C3A O3A C11A 97.1(9) . . . . ?
C2A C3A O3A C11A -142.4(8) . . . . ?
C3A O3A C11A O11A -0.9(13) . . . . ?
C3A O3A C11A C12A -177.0(7) . . . . ?
C5A C4A O4A C13A -137.9(8) . . . . ?
C3A C4A O4A C13A 103.0(9) . . . . ?
C4A O4A C13A O13A -5.1(13) . . . . ?
C4A O4A C13A C14A 176.2(8) . . . . ?
C4A C5A O5A C15A -119.8(8) . . . . ?
C6A C5A O5A C15A 119.1(9) . . . . ?
C5A O5A C15A O15A -7.1(14) . . . . ?
C5A O5A C15A C16A 177.1(8) . . . . ?
C7B C1B C2B O2B -61.3(8) . . . . ?
C6B C1B C2B O2B 178.8(7) . . . . ?
C7B C1B C2B C3B 178.8(7) . . . . ?
C6B C1B C2B C3B 58.9(9) . . . . ?
O2B C2B C3B O3B 76.0(7) . . . . ?
C1B C2B C3B O3B -167.7(6) . . . . ?
O2B C2B C3B C4B -170.1(6) . . . . ?
C1B C2B C3B C4B -53.7(9) . . . . ?
O3B C3B C4B O4B -71.8(7) . . . . ?
C2B C3B C4B O4B 170.5(6) . . . . ?
O3B C3B C4B C5B 169.1(6) . . . . ?
C2B C3B C4B C5B 51.4(9) . . . . ?
O4B C4B C5B O5B 67.9(8) . . . . ?
C3B C4B C5B O5B -173.6(6) . . . . ?
O4B C4B C5B C6B -172.6(6) . . . . ?
C3B C4B C5B C6B -54.1(9) . . . . ?
O5B C5B C6B C1B 173.5(7) . . . . ?
C4B C5B C6B C1B 56.9(9) . . . . ?
C7B C1B C6B C5B -179.7(7) . . . . ?
C2B C1B C6B C5B -59.3(9) . . . . ?
C2B C1B C7B O7B -60.8(11) . . . . ?
C6B C1B C7B O7B 59.8(11) . . . . ?
C2B C1B C7B O8B 119.0(7) . . . . ?
C6B C1B C7B O8B -120.4(8) . . . . ?
O7B C7B O8B C8B 4.1(12) . . . . ?
C1B C7B O8B C8B -175.7(7) . . . . ?
C3B C2B O2B C9B -99.0(9) . . . . ?
C1B C2B O2B C9B 140.2(8) . . . . ?
C2B O2B C9B O9B 3.2(13) . . . . ?
C2B O2B C9B C10B -176.7(7) . . . . ?
C2B C3B O3B C11B -98.3(8) . . . . ?
C4B C3B O3B C11B 143.3(7) . . . . ?
C3B O3B C11B O11B 2.5(12) . . . . ?
C3B O3B C11B C12B -179.9(7) . . . . ?
C3B C4B O4B C13B 126.7(7) . . . . ?
C5B C4B O4B C13B -110.7(7) . . . . ?
C4B O4B C13B O13B -4.0(12) . . . . ?
C4B O4B C13B C14B 178.3(7) . . . . ?
C4B C5B O5B C15B -156.5(7) . . . . ?
C6B C5B O5B C15B 83.2(9) . . . . ?
C5B O5B C15B O15B 2.2(12) . . . . ?
C5B O5B C15B C16B -178.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062