# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data___a
_database_code_depnum_ccdc_archive 'CCDC 914022'
#TrackingRef '15903_web_deposit_cif_file_0_DaisukeUrabe_1354686458.compound 16.cif'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C15 H18 O6 '
_chemical_formula_moiety         'C15 H18 O6 '
_chemical_formula_weight         294.30
_chemical_melting_point          ?
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.7664(10)
_cell_length_b                   9.3670(7)
_cell_length_c                   10.8858(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.268(3)
_cell_angle_gamma                90.0000
_cell_volume                     1385.40(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    150.0
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624.00
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
Higashi, T. (1999). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.966
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9558
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_theta_max         27.50
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
Refinement was performed using all reflections. The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^.
R-factor (gt) are based on F. The threshold expression of
F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt).
;
_reflns_number_total             1578
_reflns_number_gt                1470
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1840
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         1578
_refine_ls_number_parameters     105
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0074Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
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 0.04786(6) 0.40192(8) 0.67076(7) 0.0130(2) Uani 1.00 1 d . . .
O2 O 0.23013(6) 0.28206(9) 0.81412(8) 0.0200(2) Uani 1.00 1 d . . .
O3 O -0.09880(6) 0.24901(8) 0.48808(7) 0.0191(2) Uani 1.00 1 d . . .
C1 C 0.09329(7) 0.14384(11) 0.69542(10) 0.0125(3) Uani 1.00 1 d . . .
C2 C 0.03961(8) 0.00692(12) 0.72165(10) 0.0155(3) Uani 1.00 1 d . . .
C3 C 0.15950(7) 0.17423(11) 0.82187(9) 0.0138(2) Uani 1.00 1 d . . .
C4 C 0.0000 0.49499(16) 0.7500 0.0130(3) Uani 1.00 2 d S . .
C5 C 0.01426(8) 0.26230(11) 0.68535(9) 0.0101(2) Uani 1.00 1 d . . .
C6 C -0.08280(8) 0.22720(11) 0.59886(10) 0.0121(2) Uani 1.00 1 d . . .
C7 C -0.07844(8) 0.58318(12) 0.67128(12) 0.0198(3) Uani 1.00 1 d . . .
C8 C 0.14733(8) 0.13245(13) 0.58474(11) 0.0175(3) Uani 1.00 1 d . . .
H1 H 0.0636 -0.0814 0.6960 0.019 Uiso 1.00 1 c R . .
H2 H 0.1904 0.0891 0.8558 0.016 Uiso 1.00 1 c R . .
H3 H -0.1249 0.5214 0.6240 0.024 Uiso 1.00 1 c R . .
H4 H -0.1109 0.6411 0.7238 0.024 Uiso 1.00 1 c R . .
H5 H 0.1014 0.1226 0.5102 0.022 Uiso 1.00 1 c R . .
H6 H 0.1854 0.2163 0.5802 0.022 Uiso 1.00 1 c R . .
H7 H 0.1895 0.0516 0.5950 0.021 Uiso 1.00 1 c R . .
H8 H -0.0490 0.6423 0.6167 0.024 Uiso 1.00 1 c R . .
H9 H 0.2811 0.2680 0.8774 0.025 Uiso 1.00 1 c 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0119(4) 0.0123(5) 0.0155(5) 0.0007(2) 0.0046(3) 0.0009(2)
O2 0.0108(5) 0.0261(5) 0.0220(5) -0.0033(3) -0.0002(3) 0.0033(3)
O3 0.0136(5) 0.0302(5) 0.0120(5) 0.0014(3) -0.0026(3) 0.0007(2)
C1 0.0102(6) 0.0143(6) 0.0129(6) 0.0022(3) 0.0015(4) -0.0004(3)
C2 0.0159(6) 0.0124(6) 0.0169(6) 0.0021(3) -0.0011(4) -0.0004(3)
C3 0.0087(5) 0.0176(6) 0.0142(6) 0.0013(3) -0.0011(4) 0.0032(3)
C4 0.0128(7) 0.0126(7) 0.0145(7) 0.0000 0.0047(5) 0.0000
C5 0.0082(5) 0.0118(6) 0.0099(6) 0.0001(3) 0.0002(4) 0.0010(3)
C6 0.0102(6) 0.0127(5) 0.0127(5) 0.0021(3) -0.0008(4) -0.0030(3)
C7 0.0165(6) 0.0179(6) 0.0249(6) 0.0054(4) 0.0033(4) 0.0039(4)
C8 0.0151(6) 0.0216(6) 0.0159(6) 0.0051(4) 0.0034(4) -0.0015(4)
#==============================================================================
_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR2004
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.8'
_computing_molecular_graphics    ?
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O(1) C(4) 1.4564(12) yes . .
O(1) C(5) 1.4047(12) yes . .
O(2) C(3) 1.4139(13) yes . .
O(3) C(6) 1.2079(13) yes . .
C(1) C(2) 1.5299(15) yes . .
C(1) C(3) 1.5500(13) yes . .
C(1) C(5) 1.5455(14) yes . .
C(1) C(8) 1.5183(16) yes . .
C(2) C(2) 1.3368(16) yes . 2_556
C(3) C(6) 1.5489(15) yes . 2_556
C(4) C(7) 1.5115(13) yes . .
C(4) C(7) 1.5115(13) yes . 2_556
C(5) C(5) 1.5210(14) yes . 2_556
C(5) C(6) 1.5410(14) yes . .
O(2) H(9) 0.910 no . .
C(2) H(1) 0.950 no . .
C(3) H(2) 0.950 no . .
C(7) H(3) 0.950 no . .
C(7) H(4) 0.950 no . .
C(7) H(8) 0.950 no . .
C(8) H(5) 0.950 no . .
C(8) H(6) 0.950 no . .
C(8) H(7) 0.950 no . .
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C(4) O(1) C(5) 107.56(8) yes . . .
C(2) C(1) C(3) 102.76(8) yes . . .
C(2) C(1) C(5) 105.04(8) yes . . .
C(2) C(1) C(8) 113.72(9) yes . . .
C(3) C(1) C(5) 103.75(8) yes . . .
C(3) C(1) C(8) 115.11(8) yes . . .
C(5) C(1) C(8) 115.05(8) yes . . .
C(1) C(2) C(2) 122.73(10) yes . . 2_556
O(2) C(3) C(1) 112.95(8) yes . . .
O(2) C(3) C(6) 109.96(8) yes . . 2_556
C(1) C(3) C(6) 101.39(7) yes . . 2_556
O(1) C(4) O(1) 106.46(10) yes . . 2_556
O(1) C(4) C(7) 109.96(5) yes . . .
O(1) C(4) C(7) 108.23(5) yes . . 2_556
O(1) C(4) C(7) 108.23(5) yes 2_556 . .
O(1) C(4) C(7) 109.96(5) yes 2_556 . 2_556
C(7) C(4) C(7) 113.74(11) yes . . 2_556
O(1) C(5) C(1) 115.82(8) yes . . .
O(1) C(5) C(5) 104.09(8) yes . . 2_556
O(1) C(5) C(6) 113.48(8) yes . . .
C(1) C(5) C(5) 102.59(8) yes . . 2_556
C(1) C(5) C(6) 114.92(8) yes . . .
C(5) C(5) C(6) 103.75(8) yes 2_556 . .
O(3) C(6) C(3) 125.40(9) yes . . 2_556
O(3) C(6) C(5) 125.08(10) yes . . .
C(3) C(6) C(5) 109.25(8) yes 2_556 . .
C(3) O(2) H(9) 107.7 no . . .
C(1) C(2) H(1) 118.3 no . . .
C(2) C(2) H(1) 119.0 no 2_556 . .
O(2) C(3) H(2) 110.7 no . . .
C(1) C(3) H(2) 110.7 no . . .
C(6) C(3) H(2) 110.8 no 2_556 . .
C(4) C(7) H(3) 109.4 no . . .
C(4) C(7) H(4) 109.5 no . . .
C(4) C(7) H(8) 109.6 no . . .
H(3) C(7) H(4) 109.5 no . . .
H(3) C(7) H(8) 109.5 no . . .
H(4) C(7) H(8) 109.5 no . . .
C(1) C(8) H(5) 109.9 no . . .
C(1) C(8) H(6) 109.1 no . . .
C(1) C(8) H(7) 109.4 no . . .
H(5) C(8) H(6) 109.5 no . . .
H(5) C(8) H(7) 109.5 no . . .
H(6) C(8) H(7) 109.5 no . . .
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C(4) O(1) C(5) C(1) -137.90(7) ? . . . .
C(4) O(1) C(5) C(6) 85.99(9) ? . . . .
C(4) O(1) C(5) C(5) -26.11(8) ? . . . 2_556
C(5) O(1) C(4) O(1) 10.71(7) ? . . . 2_556
C(5) O(1) C(4) C(7) -106.31(9) ? . . . .
C(5) O(1) C(4) C(7) 128.89(9) ? . . . 2_556
C(2) C(1) C(3) O(2) 168.92(8) ? . . . .
C(2) C(1) C(3) C(6) -73.46(9) ? . . . 2_556
C(3) C(1) C(2) C(2) 81.40(11) ? . . . 2_556
C(2) C(1) C(5) O(1) 175.26(8) ? . . . .
C(2) C(1) C(5) C(6) -49.27(11) ? . . . .
C(2) C(1) C(5) C(5) 62.60(9) ? . . . 2_556
C(5) C(1) C(2) C(2) -26.85(12) ? . . . 2_556
C(8) C(1) C(2) C(2) -153.51(9) ? . . . 2_556
C(3) C(1) C(5) O(1) 67.73(10) ? . . . .
C(3) C(1) C(5) C(6) -156.79(8) ? . . . .
C(3) C(1) C(5) C(5) -44.93(9) ? . . . 2_556
C(5) C(1) C(3) O(2) -81.85(10) ? . . . .
C(5) C(1) C(3) C(6) 35.76(9) ? . . . 2_556
C(8) C(1) C(3) O(2) 44.75(12) ? . . . .
C(8) C(1) C(3) C(6) 162.36(8) ? . . . 2_556
C(8) C(1) C(5) O(1) -58.91(11) ? . . . .
C(8) C(1) C(5) C(6) 76.57(11) ? . . . .
C(8) C(1) C(5) C(5) -171.56(8) ? . . . 2_556
C(1) C(2) C(2) C(1) 9.52(15) ? . . 2_556 2_556
O(2) C(3) C(6) O(3) -68.91(12) ? . . 2_556 2_556
O(2) C(3) C(6) C(5) 105.39(8) ? . . 2_556 2_556
C(1) C(3) C(6) O(3) 171.33(10) ? . . 2_556 2_556
C(1) C(3) C(6) C(5) -14.37(10) ? . . 2_556 2_556
O(1) C(5) C(5) O(1) 32.57(9) ? . . 2_556 2_556
O(1) C(5) C(5) C(1) 153.65(7) ? . . 2_556 2_556
O(1) C(5) C(5) C(6) -86.41(9) ? . . 2_556 2_556
O(1) C(5) C(6) O(3) 49.36(14) ? . . . .
O(1) C(5) C(6) C(3) -124.97(9) ? . . . 2_556
C(1) C(5) C(5) O(1) 153.65(7) ? . . 2_556 2_556
C(1) C(5) C(5) C(1) -85.27(8) ? . . 2_556 2_556
C(1) C(5) C(5) C(6) 34.68(9) ? . . 2_556 2_556
C(1) C(5) C(6) O(3) -87.16(12) ? . . . .
C(1) C(5) C(6) C(3) 98.52(10) ? . . . 2_556
C(5) C(5) C(6) O(3) 161.66(10) ? 2_556 . . .
C(5) C(5) C(6) C(3) -12.66(10) ? 2_556 . . 2_556
C(6) C(5) C(5) O(1) -86.41(9) ? . . 2_556 2_556
C(6) C(5) C(5) C(1) 34.68(9) ? . . 2_556 2_556
C(6) C(5) C(5) C(6) 154.62(8) ? . . 2_556 2_556
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O(1) O(1) 2.3334(11) ? . 2_556
O(1) O(2) 2.9548(10) ? . .
O(1) O(3) 2.9647(10) ? . .
O(1) C(1) 2.5006(12) ? . .
O(1) C(1) 3.5572(13) ? . 2_556
O(1) C(3) 2.9669(12) ? . .
O(1) C(3) 3.5746(12) ? . 2_556
O(1) C(5) 2.3079(13) ? . 2_556
O(1) C(6) 2.4643(12) ? . .
O(1) C(6) 2.9683(12) ? . 2_556
O(1) C(7) 2.4308(13) ? . .
O(1) C(7) 2.4049(14) ? . 2_556
O(1) C(8) 3.0881(14) ? . .
O(2) O(1) 2.9548(10) ? . .
O(2) O(3) 3.0422(12) ? . 2_556
O(2) O(3) 2.7893(10) ? . 8_555
O(2) C(1) 2.4720(12) ? . .
O(2) C(5) 3.0804(12) ? . .
O(2) C(5) 3.3704(13) ? . 2_556
O(2) C(6) 2.4277(14) ? . 2_556
O(2) C(7) 3.5283(14) ? . 2_556
O(2) C(8) 2.9294(14) ? . .
O(3) O(1) 2.9647(10) ? . .
O(3) O(2) 3.0422(12) ? . 2_556
O(3) O(2) 2.7893(10) ? . 8_454
O(3) C(1) 3.3369(11) ? . .
O(3) C(1) 3.5725(13) ? . 2_556
O(3) C(2) 3.4961(13) ? . 3_556
O(3) C(3) 2.4548(13) ? . 2_556
O(3) C(3) 3.5948(11) ? . 8_454
O(3) C(5) 2.4440(11) ? . .
O(3) C(5) 3.5602(11) ? . 2_556
O(3) C(7) 3.5773(15) ? . 3_566
O(3) C(8) 3.5541(13) ? . .
C(1) O(1) 2.5006(12) ? . .
C(1) O(1) 3.5572(13) ? . 2_556
C(1) O(2) 2.4720(12) ? . .
C(1) O(3) 3.3369(11) ? . .
C(1) O(3) 3.5725(13) ? . 2_556
C(1) C(1) 2.9987(15) ? . 2_556
C(1) C(2) 2.5178(15) ? . 2_556
C(1) C(3) 3.4664(13) ? . 2_556
C(1) C(5) 2.3931(15) ? . 2_556
C(1) C(6) 2.6020(13) ? . .
C(1) C(6) 2.3979(15) ? . 2_556
C(2) O(3) 3.4961(13) ? . 3_556
C(2) C(1) 2.5178(15) ? . 2_556
C(2) C(3) 2.4063(14) ? . .
C(2) C(3) 3.1266(14) ? . 2_556
C(2) C(5) 2.4405(15) ? . .
C(2) C(5) 2.7457(15) ? . 2_556
C(2) C(6) 2.8563(14) ? . .
C(2) C(6) 2.8380(15) ? . 2_556
C(2) C(8) 2.5524(17) ? . .
C(3) O(1) 2.9669(12) ? . .
C(3) O(1) 3.5746(12) ? . 2_556
C(3) O(3) 2.4548(13) ? . 2_556
C(3) O(3) 3.5948(11) ? . 8_555
C(3) C(1) 3.4664(13) ? . 2_556
C(3) C(2) 2.4063(14) ? . .
C(3) C(2) 3.1266(14) ? . 2_556
C(3) C(5) 2.4351(13) ? . .
C(3) C(5) 2.5195(14) ? . 2_556
C(3) C(8) 2.5895(15) ? . .
C(4) C(5) 2.3085(17) ? . .
C(4) C(5) 2.3085(17) ? . 2_556
C(4) C(6) 3.1135(15) ? . .
C(4) C(6) 3.1135(15) ? . 2_556
C(5) O(1) 2.3079(13) ? . 2_556
C(5) O(2) 3.0804(12) ? . .
C(5) O(2) 3.3704(13) ? . 2_556
C(5) O(3) 2.4440(11) ? . .
C(5) O(3) 3.5602(11) ? . 2_556
C(5) C(1) 2.3931(15) ? . 2_556
C(5) C(2) 2.4405(15) ? . .
C(5) C(2) 2.7457(15) ? . 2_556
C(5) C(3) 2.4351(13) ? . .
C(5) C(3) 2.5195(14) ? . 2_556
C(5) C(4) 2.3085(17) ? . .
C(5) C(6) 2.4088(13) ? . 2_556
C(5) C(7) 3.2593(15) ? . .
C(5) C(7) 3.4360(15) ? . 2_556
C(5) C(8) 2.5848(16) ? . .
C(6) O(1) 2.4643(12) ? . .
C(6) O(1) 2.9683(12) ? . 2_556
C(6) O(2) 2.4277(14) ? . 2_556
C(6) C(1) 2.6020(13) ? . .
C(6) C(1) 2.3979(15) ? . 2_556
C(6) C(2) 2.8563(14) ? . .
C(6) C(2) 2.8380(15) ? . 2_556
C(6) C(4) 3.1135(15) ? . .
C(6) C(5) 2.4088(13) ? . 2_556
C(6) C(7) 3.4247(15) ? . .
C(6) C(8) 3.3173(15) ? . .
C(7) O(1) 2.4308(13) ? . .
C(7) O(1) 2.4049(14) ? . 2_556
C(7) O(2) 3.5283(14) ? . 2_556
C(7) O(3) 3.5773(15) ? . 3_566
C(7) C(5) 3.2593(15) ? . .
C(7) C(5) 3.4360(15) ? . 2_556
C(7) C(6) 3.4247(15) ? . .
C(7) C(7) 2.5317(15) ? . 2_556
C(8) O(1) 3.0881(14) ? . .
C(8) O(2) 2.9294(14) ? . .
C(8) O(3) 3.5541(13) ? . .
C(8) C(2) 2.5524(17) ? . .
C(8) C(3) 2.5895(15) ? . .
C(8) C(5) 2.5848(16) ? . .
C(8) C(6) 3.3173(15) ? . .
O(1) H(3) 2.603 ? . .
O(1) H(3) 2.570 ? . 2_556
O(1) H(4) 3.246 ? . .
O(1) H(4) 2.602 ? . 2_556
O(1) H(5) 3.296 ? . .
O(1) H(6) 2.860 ? . .
O(1) H(8) 2.634 ? . .
O(1) H(8) 3.227 ? . 2_556
O(1) H(8) 3.159 ? . 3_566
O(2) H(1) 3.132 ? . 6_556
O(2) H(2) 1.962 ? . .
O(2) H(3) 2.810 ? . 2_556
O(2) H(4) 2.862 ? . 5_545
O(2) H(6) 2.595 ? . .
O(2) H(7) 3.199 ? . .
O(2) H(7) 2.868 ? . 6_556
O(2) H(9) 3.418 ? . 7_557
O(3) H(1) 2.650 ? . 3_556
O(3) H(2) 2.723 ? . 2_556
O(3) H(2) 3.383 ? . 8_454
O(3) H(3) 3.000 ? . .
O(3) H(4) 3.035 ? . 4_564
O(3) H(5) 2.973 ? . .
O(3) H(5) 3.481 ? . 3_556
O(3) H(7) 3.153 ? . 3_556
O(3) H(8) 2.687 ? . 3_566
O(3) H(9) 3.107 ? . 2_556
O(3) H(9) 1.889 ? . 8_454
C(1) H(1) 2.149 ? . .
C(1) H(1) 3.368 ? . 2_556
C(1) H(2) 2.085 ? . .
C(1) H(5) 2.047 ? . .
C(1) H(6) 2.038 ? . .
C(1) H(7) 2.041 ? . .
C(1) H(9) 3.211 ? . .
C(2) H(1) 1.980 ? . 2_556
C(2) H(2) 2.462 ? . .
C(2) H(2) 3.236 ? . 2_556
C(2) H(4) 3.588 ? . 2_546
C(2) H(5) 2.798 ? . .
C(2) H(5) 3.167 ? . 3_556
C(2) H(5) 3.346 ? . 4_555
C(2) H(6) 3.353 ? . .
C(2) H(7) 2.693 ? . .
C(3) H(1) 2.962 ? . .
C(3) H(3) 3.353 ? . 2_556
C(3) H(4) 3.509 ? . 5_545
C(3) H(5) 3.393 ? . .
C(3) H(6) 2.739 ? . .
C(3) H(7) 2.814 ? . .
C(3) H(9) 1.900 ? . .
C(3) H(9) 3.288 ? . 7_557
C(4) H(3) 2.034 ? . .
C(4) H(3) 2.034 ? . 2_556
C(4) H(4) 2.036 ? . .
C(4) H(4) 2.036 ? . 2_556
C(4) H(8) 2.037 ? . .
C(4) H(8) 2.037 ? . 2_556
C(5) H(1) 3.289 ? . .
C(5) H(2) 3.241 ? . .
C(5) H(2) 3.220 ? . 2_556
C(5) H(3) 3.097 ? . .
C(5) H(3) 3.391 ? . 2_556
C(5) H(5) 2.743 ? . .
C(5) H(6) 2.813 ? . .
C(5) H(7) 3.384 ? . .
C(5) H(8) 3.513 ? . 3_566
C(6) H(1) 3.585 ? . .
C(6) H(1) 3.536 ? . 3_556
C(6) H(2) 2.085 ? . 2_556
C(6) H(3) 2.838 ? . .
C(6) H(5) 3.018 ? . .
C(6) H(5) 3.480 ? . 3_556
C(6) H(7) 3.526 ? . 3_556
C(6) H(8) 3.415 ? . 3_566
C(6) H(9) 2.808 ? . 2_556
C(6) H(9) 2.805 ? . 8_454
C(7) H(1) 3.450 ? . 2_566
C(7) H(3) 3.336 ? . 2_556
C(7) H(4) 2.727 ? . 2_556
C(7) H(5) 3.376 ? . 3_566
C(7) H(6) 3.448 ? . 3_566
C(7) H(6) 3.474 ? . 5_455
C(7) H(7) 3.182 ? . 5_455
C(7) H(8) 2.722 ? . 2_556
C(8) H(1) 2.694 ? . .
C(8) H(2) 2.943 ? . .
C(8) H(2) 3.369 ? . 4_554
C(8) H(3) 3.266 ? . 5_545
C(8) H(4) 3.428 ? . 5_545
C(8) H(6) 3.445 ? . 7_556
C(8) H(8) 3.184 ? . 3_566
C(8) H(9) 3.559 ? . 6_546
H(1) O(2) 3.132 ? . 6_546
H(1) O(3) 2.650 ? . 3_556
H(1) C(1) 2.149 ? . .
H(1) C(1) 3.368 ? . 2_556
H(1) C(2) 1.980 ? . 2_556
H(1) C(3) 2.962 ? . .
H(1) C(5) 3.289 ? . .
H(1) C(6) 3.585 ? . .
H(1) C(6) 3.536 ? . 3_556
H(1) C(7) 3.450 ? . 2_546
H(1) C(8) 2.694 ? . .
H(1) H(1) 2.262 ? . 2_556
H(1) H(2) 2.766 ? . .
H(1) H(4) 3.585 ? . 1_545
H(1) H(4) 2.786 ? . 2_546
H(1) H(5) 2.890 ? . .
H(1) H(5) 2.950 ? . 3_556
H(1) H(5) 3.398 ? . 4_555
H(1) H(6) 3.585 ? . .
H(1) H(7) 2.526 ? . .
H(1) H(8) 3.068 ? . 1_545
H(1) H(8) 3.321 ? . 2_546
H(1) H(9) 2.784 ? . 6_546
H(2) O(2) 1.962 ? . .
H(2) O(3) 2.723 ? . 2_556
H(2) O(3) 3.383 ? . 8_555
H(2) C(1) 2.085 ? . .
H(2) C(2) 2.462 ? . .
H(2) C(2) 3.236 ? . 2_556
H(2) C(5) 3.241 ? . .
H(2) C(5) 3.220 ? . 2_556
H(2) C(6) 2.085 ? . 2_556
H(2) C(8) 2.943 ? . .
H(2) C(8) 3.369 ? . 4_555
H(2) H(1) 2.766 ? . .
H(2) H(4) 3.324 ? . 5_545
H(2) H(5) 2.987 ? . 4_555
H(2) H(6) 3.218 ? . .
H(2) H(7) 2.859 ? . .
H(2) H(7) 2.920 ? . 4_555
H(2) H(9) 2.079 ? . .
H(2) H(9) 3.164 ? . 7_557
H(3) O(1) 2.603 ? . .
H(3) O(1) 2.571 ? . 2_556
H(3) O(2) 2.810 ? . 2_556
H(3) O(3) 3.000 ? . .
H(3) C(3) 3.353 ? . 2_556
H(3) C(4) 2.034 ? . .
H(3) C(5) 3.097 ? . .
H(3) C(5) 3.391 ? . 2_556
H(3) C(6) 2.838 ? . .
H(3) C(7) 3.336 ? . 2_556
H(3) C(8) 3.266 ? . 5_455
H(3) H(4) 1.551 ? . .
H(3) H(4) 3.579 ? . 2_556
H(3) H(6) 3.328 ? . 3_566
H(3) H(6) 3.160 ? . 5_455
H(3) H(7) 2.539 ? . 5_455
H(3) H(8) 1.551 ? . .
H(3) H(8) 3.578 ? . 2_556
H(3) H(9) 3.201 ? . 2_556
H(4) O(1) 3.246 ? . .
H(4) O(1) 2.602 ? . 2_556
H(4) O(2) 2.862 ? . 5_455
H(4) O(3) 3.035 ? . 4_565
H(4) C(2) 3.588 ? . 2_566
H(4) C(3) 3.509 ? . 5_455
H(4) C(4) 2.036 ? . .
H(4) C(7) 2.727 ? . 2_556
H(4) C(8) 3.428 ? . 5_455
H(4) H(1) 3.585 ? . 1_565
H(4) H(1) 2.786 ? . 2_566
H(4) H(2) 3.324 ? . 5_455
H(4) H(3) 1.551 ? . .
H(4) H(3) 3.579 ? . 2_556
H(4) H(4) 3.015 ? . 2_556
H(4) H(5) 3.393 ? . 3_566
H(4) H(6) 3.563 ? . 3_566
H(4) H(6) 3.064 ? . 5_455
H(4) H(7) 2.996 ? . 5_455
H(4) H(8) 1.551 ? . .
H(4) H(8) 2.575 ? . 2_556
H(4) H(9) 2.688 ? . 5_455
H(5) O(1) 3.296 ? . .
H(5) O(3) 2.973 ? . .
H(5) O(3) 3.481 ? . 3_556
H(5) C(1) 2.047 ? . .
H(5) C(2) 2.798 ? . .
H(5) C(2) 3.167 ? . 3_556
H(5) C(2) 3.346 ? . 4_554
H(5) C(3) 3.393 ? . .
H(5) C(5) 2.743 ? . .
H(5) C(6) 3.018 ? . .
H(5) C(6) 3.480 ? . 3_556
H(5) C(7) 3.376 ? . 3_566
H(5) H(1) 2.890 ? . .
H(5) H(1) 2.950 ? . 3_556
H(5) H(1) 3.398 ? . 4_554
H(5) H(2) 2.987 ? . 4_554
H(5) H(4) 3.393 ? . 3_566
H(5) H(5) 3.594 ? . 3_556
H(5) H(6) 1.551 ? . .
H(5) H(6) 3.577 ? . 7_556
H(5) H(7) 1.551 ? . .
H(5) H(8) 2.638 ? . 3_566
H(6) O(1) 2.860 ? . .
H(6) O(2) 2.595 ? . .
H(6) C(1) 2.038 ? . .
H(6) C(2) 3.353 ? . .
H(6) C(3) 2.739 ? . .
H(6) C(5) 2.813 ? . .
H(6) C(7) 3.448 ? . 3_566
H(6) C(7) 3.474 ? . 5_545
H(6) C(8) 3.445 ? . 7_556
H(6) H(1) 3.585 ? . .
H(6) H(2) 3.218 ? . .
H(6) H(3) 3.328 ? . 3_566
H(6) H(3) 3.160 ? . 5_545
H(6) H(4) 3.563 ? . 3_566
H(6) H(4) 3.064 ? . 5_545
H(6) H(5) 1.551 ? . .
H(6) H(5) 3.577 ? . 7_556
H(6) H(6) 2.760 ? . 7_556
H(6) H(7) 1.551 ? . .
H(6) H(7) 3.519 ? . 7_556
H(6) H(8) 2.929 ? . 3_566
H(6) H(9) 3.326 ? . .
H(7) O(2) 3.199 ? . .
H(7) O(2) 2.868 ? . 6_546
H(7) O(3) 3.153 ? . 3_556
H(7) C(1) 2.041 ? . .
H(7) C(2) 2.693 ? . .
H(7) C(3) 2.814 ? . .
H(7) C(5) 3.384 ? . .
H(7) C(6) 3.526 ? . 3_556
H(7) C(7) 3.182 ? . 5_545
H(7) H(1) 2.526 ? . .
H(7) H(2) 2.859 ? . .
H(7) H(2) 2.920 ? . 4_554
H(7) H(3) 2.539 ? . 5_545
H(7) H(4) 2.996 ? . 5_545
H(7) H(5) 1.551 ? . .
H(7) H(6) 1.551 ? . .
H(7) H(6) 3.519 ? . 7_556
H(7) H(9) 2.697 ? . 6_546
H(8) O(1) 2.634 ? . .
H(8) O(1) 3.227 ? . 2_556
H(8) O(1) 3.159 ? . 3_566
H(8) O(3) 2.687 ? . 3_566
H(8) C(4) 2.037 ? . .
H(8) C(5) 3.513 ? . 3_566
H(8) C(6) 3.415 ? . 3_566
H(8) C(7) 2.722 ? . 2_556
H(8) C(8) 3.184 ? . 3_566
H(8) H(1) 3.068 ? . 1_565
H(8) H(1) 3.321 ? . 2_566
H(8) H(3) 1.551 ? . .
H(8) H(3) 3.578 ? . 2_556
H(8) H(4) 1.551 ? . .
H(8) H(4) 2.575 ? . 2_556
H(8) H(5) 2.638 ? . 3_566
H(8) H(6) 2.929 ? . 3_566
H(8) H(8) 2.997 ? . 2_556
H(9) O(2) 3.418 ? . 7_557
H(9) O(3) 3.107 ? . 2_556
H(9) O(3) 1.889 ? . 8_555
H(9) C(1) 3.211 ? . .
H(9) C(3) 1.900 ? . .
H(9) C(3) 3.288 ? . 7_557
H(9) C(6) 2.808 ? . 2_556
H(9) C(6) 2.805 ? . 8_555
H(9) C(8) 3.559 ? . 6_556
H(9) H(1) 2.784 ? . 6_556
H(9) H(2) 2.079 ? . .
H(9) H(2) 3.164 ? . 7_557
H(9) H(3) 3.201 ? . 2_556
H(9) H(4) 2.688 ? . 5_545
H(9) H(6) 3.326 ? . .
H(9) H(7) 2.697 ? . 6_556
H(9) H(9) 2.949 ? . 7_557


data_I
_database_code_depnum_ccdc_archive 'CCDC 914023'
#TrackingRef '15904_web_deposit_cif_file_1_DaisukeUrabe_1354686458.compound 1.cif'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H32 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         372.45
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   9.1857(14)
_cell_length_b                   10.7306(16)
_cell_length_c                   17.807(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.071(2)
_cell_angle_gamma                90
_cell_volume                     1750.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2101
_cell_measurement_theta_min      2.9233
_cell_measurement_theta_max      25.0241
_cell_measurement_temperature    93.0(2)
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.99
_exptl_special_details           
;
;
_diffrn_ambient_temperature      93.0(2)
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Tourbo X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  
'Bruker Helios, a multilayered conforcal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8411
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_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.
;
_reflns_number_total             3195
_reflns_number_gt                2582
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0967
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.5543P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
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'
_computing_data_collection       'Bruker SMART APEXII ULTRA'
_computing_cell_refinement       'SAINT V8.26A (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.26A (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.65254(13) 0.22743(11) -0.03955(7) 0.0139(3) Uani d . 1 . .
O O3 0.75749(14) -0.01611(10) 0.05593(7) 0.0135(3) Uani d . 1 . .
O O5 0.96199(15) 0.01695(11) 0.16009(7) 0.0146(3) Uani d . 1 . .
O O1 0.36765(13) 0.14535(11) 0.07577(7) 0.0132(3) Uani d . 1 . .
O O8 0.76941(13) 0.28886(10) 0.22592(6) 0.0124(3) Uani d . 1 . .
O O6 0.58971(14) 0.00876(12) 0.17693(7) 0.0149(3) Uani d . 1 . .
C C26 0.9705(2) 0.18818(19) 0.02769(11) 0.0148(4) Uani d . 1 . .
C C27 0.4673(2) 0.24413(18) 0.21291(10) 0.0148(4) Uani d . 1 . .
C C9 0.86313(18) 0.19466(16) 0.08838(9) 0.0116(4) Uani d . 1 . .
C C10 1.0591(2) 0.21373(18) 0.20496(10) 0.0148(4) Uani d . 1 . .
C C11 0.56735(19) 0.23426(15) 0.14794(9) 0.0113(4) Uani d . 1 . .
C C12 0.66454(19) 0.11697(15) 0.15641(9) 0.0112(4) Uani d . 1 . .
C C13 0.69209(19) 0.33108(16) 0.15740(9) 0.0118(4) Uani d . 1 . .
C C14 0.60299(19) 0.15655(16) 0.02085(9) 0.0117(4) Uani d . 1 . .
C C15 0.8027(2) 0.32802(16) 0.09726(10) 0.0125(4) Uani d . 1 . .
C C16 0.79494(19) 0.15702(15) 0.21300(9) 0.0119(4) Uani d . 1 . .
C C17 0.3490(2) 0.32768(18) -0.04431(10) 0.0158(4) Uani d . 1 . .
C C18 0.4375(2) 0.34942(16) 0.03082(10) 0.0133(4) Uani d . 1 . .
C C19 0.92863(19) 0.14852(15) 0.16607(9) 0.0121(4) Uani d . 1 . .
C C20 1.0927(2) 0.15617(19) 0.28301(10) 0.0182(4) Uani d . 1 . .
C C21 0.49106(19) 0.22655(15) 0.06747(9) 0.0121(4) Uani d . 1 . .
C C22 0.9594(2) 0.15526(19) 0.33015(10) 0.0183(4) Uani d . 1 . .
C C23 0.8226(2) 0.09689(18) 0.28903(10) 0.0157(4) Uani d . 1 . .
C C24 0.3480(2) 0.42822(18) 0.08163(11) 0.0165(4) Uani d . 1 . .
C C25 0.72547(19) 0.10922(15) 0.07715(9) 0.0106(4) Uani d . 1 . .
O O9W 0.74863(14) 0.06079(13) 0.85282(7) 0.0157(3) Uani d . 1 . .
H H2 0.5548(19) 0.0842(17) -0.0012(10) 0.009(4) Uiso d . 1 . .
H H1 0.525(2) 0.3972(16) 0.0185(9) 0.010(4) Uiso d . 1 . .
H H18 0.936(2) 0.2429(17) 0.3433(10) 0.012(5) Uiso d . 1 . .
H H3 0.406(2) 0.4590(16) 0.1246(10) 0.008(4) Uiso d . 1 . .
H H7 0.328(2) 0.405(2) -0.0694(11) 0.022(5) Uiso d . 1 . .
H H9 0.6568(19) 0.4169(17) 0.1675(9) 0.009(4) Uiso d . 1 . .
H H14 1.040(2) 0.3007(18) 0.2094(10) 0.015(5) Uiso d . 1 . .
H H17 1.129(2) 0.0690(18) 0.2774(10) 0.018(5) Uiso d . 1 . .
H H11 0.885(2) 0.3849(17) 0.1135(10) 0.014(5) Uiso d . 1 . .
H H4 0.268(2) 0.3788(18) 0.0993(10) 0.018(5) Uiso d . 1 . .
H H6 0.253(2) 0.2908(18) -0.0366(11) 0.022(5) Uiso d . 1 . .
H H10 0.759(2) 0.3538(16) 0.0480(11) 0.015(5) Uiso d . 1 . .
H H5 0.307(2) 0.4982(18) 0.0521(11) 0.020(5) Uiso d . 1 . .
H H16 1.170(2) 0.2037(18) 0.3106(10) 0.017(5) Uiso d . 1 . .
H H15 1.144(2) 0.2068(16) 0.1766(10) 0.011(5) Uiso d . 1 . .
H H20 0.839(2) 0.0071(19) 0.2813(10) 0.017(5) Uiso d . 1 . .
H H19 0.736(2) 0.1061(18) 0.3182(10) 0.019(5) Uiso d . 1 . .
H H13 1.053(2) 0.2417(19) 0.0407(11) 0.024(6) Uiso d . 1 . .
H H8 0.524(2) 0.2275(18) 0.2593(12) 0.024(5) Uiso d . 1 . .
H H12 0.928(2) 0.213(2) -0.0202(13) 0.032(6) Uiso d . 1 . .
H H23 0.982(2) 0.1118(18) 0.3789(11) 0.021(5) Uiso d . 1 . .
H H28 0.840(3) -0.033(2) 0.0878(13) 0.035(6) Uiso d . 1 . .
H H27 0.336(3) 0.120(2) 0.0302(13) 0.037(7) Uiso d . 1 . .
H H21 0.733(3) 0.106(2) 0.8102(14) 0.040(7) Uiso d . 1 . .
H H25 0.427(2) 0.326(2) 0.2174(12) 0.035(6) Uiso d . 1 . .
H H29 1.052(3) 0.006(2) 0.1542(13) 0.042(7) Uiso d . 1 . .
H H26 0.621(2) -0.051(2) 0.1522(12) 0.032(7) Uiso d . 1 . .
H H24 0.390(3) 0.185(2) 0.2088(13) 0.043(7) Uiso d . 1 . .
H H22 0.680(3) 0.005(3) 0.8545(15) 0.064(9) Uiso d . 1 . .
H H30 0.400(2) 0.2768(18) -0.0780(11) 0.021(5) Uiso d . 1 . .
H H32 1.008(2) 0.106(2) 0.0213(11) 0.032(6) Uiso d . 1 . .
H H31 0.689(2) 0.173(2) -0.0727(13) 0.035(6) Uiso d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0171(7) 0.0150(7) 0.0100(6) 0.0017(5) 0.0040(5) 0.0007(5)
O3 0.0155(7) 0.0089(6) 0.0159(7) 0.0029(5) 0.0001(5) -0.0032(5)
O5 0.0143(7) 0.0117(6) 0.0180(7) 0.0032(5) 0.0021(5) -0.0004(5)
O1 0.0114(7) 0.0149(7) 0.0135(7) -0.0041(5) 0.0014(5) -0.0004(5)
O8 0.0148(7) 0.0115(6) 0.0107(6) 0.0013(5) -0.0008(5) -0.0009(5)
O6 0.0171(7) 0.0098(6) 0.0184(7) -0.0032(5) 0.0053(5) 0.0013(5)
C26 0.0111(10) 0.0195(11) 0.0142(10) -0.0006(8) 0.0040(7) -0.0007(8)
C27 0.0140(10) 0.0158(10) 0.0149(10) 0.0022(8) 0.0019(8) -0.0020(8)
C9 0.0105(9) 0.0128(9) 0.0116(9) -0.0011(7) 0.0018(7) 0.0004(7)
C10 0.0124(10) 0.0169(10) 0.0152(9) -0.0008(8) 0.0022(7) -0.0016(7)
C11 0.0118(9) 0.0106(9) 0.0118(9) 0.0004(7) 0.0026(7) -0.0014(7)
C12 0.0127(9) 0.0091(9) 0.0121(9) -0.0010(7) 0.0027(7) 0.0021(7)
C13 0.0141(9) 0.0102(9) 0.0109(9) 0.0011(7) -0.0006(7) -0.0011(7)
C14 0.0127(9) 0.0110(9) 0.0118(9) -0.0027(7) 0.0022(7) -0.0026(7)
C15 0.0138(9) 0.0105(9) 0.0131(9) -0.0021(7) 0.0000(7) 0.0006(7)
C16 0.0138(9) 0.0079(9) 0.0141(9) 0.0008(7) 0.0021(7) -0.0001(7)
C17 0.0156(10) 0.0146(10) 0.0171(10) 0.0017(8) -0.0009(8) 0.0011(8)
C18 0.0129(9) 0.0124(9) 0.0150(9) -0.0001(8) 0.0031(7) 0.0001(7)
C19 0.0135(9) 0.0092(9) 0.0136(9) 0.0007(7) 0.0024(7) 0.0002(7)
C20 0.0151(10) 0.0226(11) 0.0163(10) 0.0011(9) -0.0030(8) -0.0016(8)
C21 0.0117(9) 0.0116(9) 0.0130(9) -0.0019(7) 0.0016(7) -0.0013(7)
C22 0.0216(11) 0.0214(11) 0.0113(10) 0.0050(8) -0.0025(8) 0.0005(8)
C23 0.0177(10) 0.0162(10) 0.0136(10) 0.0025(8) 0.0035(8) 0.0021(7)
C24 0.0171(10) 0.0157(10) 0.0168(10) 0.0028(8) 0.0018(8) 0.0010(8)
C25 0.0112(9) 0.0090(8) 0.0120(9) 0.0006(7) 0.0028(7) -0.0021(7)
O9W 0.0177(7) 0.0156(7) 0.0142(7) -0.0013(6) 0.0039(5) 0.0022(6)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C14 . 1.418(2) ?
O2 H31 . 0.91(2) ?
O3 C25 . 1.4331(19) ?
O3 H28 . 0.93(2) ?
O5 C19 . 1.450(2) ?
O5 H29 . 0.85(3) ?
O1 C21 . 1.446(2) ?
O1 H27 . 0.89(2) ?
O8 C13 . 1.441(2) ?
O8 C16 . 1.455(2) ?
O6 C12 . 1.411(2) ?
O6 H26 . 0.84(2) ?
C26 C9 . 1.516(2) ?
C26 H13 . 0.97(2) ?
C26 H12 . 0.95(2) ?
C26 H32 . 0.95(2) ?
C27 C11 . 1.532(2) ?
C27 H8 . 0.96(2) ?
C27 H25 . 0.96(2) ?
C27 H24 . 0.95(3) ?
C9 C15 . 1.547(2) ?
C9 C19 . 1.550(2) ?
C9 C25 . 1.563(2) ?
C10 C19 . 1.512(2) ?
C10 C20 . 1.532(3) ?
C10 H14 . 0.954(19) ?
C10 H15 . 0.962(19) ?
C11 C12 . 1.544(2) ?
C11 C13 . 1.547(2) ?
C11 C21 . 1.552(2) ?
C12 C25 . 1.557(2) ?
C12 C16 . 1.569(2) ?
C13 C15 . 1.528(2) ?
C13 H9 . 0.997(18) ?
C14 C25 . 1.539(2) ?
C14 C21 . 1.559(2) ?
C14 H2 . 0.963(18) ?
C15 H11 . 0.998(19) ?
C15 H10 . 0.978(19) ?
C16 C23 . 1.505(2) ?
C16 C19 . 1.536(2) ?
C17 C18 . 1.533(3) ?
C17 H7 . 0.96(2) ?
C17 H6 . 0.98(2) ?
C17 H30 . 0.96(2) ?
C18 C24 . 1.522(2) ?
C18 C21 . 1.536(2) ?
C18 H1 . 0.992(18) ?
C20 C22 . 1.533(3) ?
C20 H17 . 1.00(2) ?
C20 H16 . 0.98(2) ?
C22 C23 . 1.542(3) ?
C22 H18 . 0.997(18) ?
C22 H23 . 0.99(2) ?
C23 H20 . 0.99(2) ?
C23 H19 . 0.99(2) ?
C24 H3 . 0.960(19) ?
C24 H4 . 0.98(2) ?
C24 H5 . 0.98(2) ?
O9W H21 . 0.91(3) ?
O9W H22 . 0.87(3) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O2 H31 . . 107.2(13) ?
C25 O3 H28 . . 101.3(14) ?
C19 O5 H29 . . 111.0(16) ?
C21 O1 H27 . . 107.4(15) ?
C13 O8 C16 . . 104.30(12) ?
C12 O6 H26 . . 107.5(15) ?
C9 C26 H13 . . 109.9(12) ?
C9 C26 H12 . . 112.5(13) ?
H13 C26 H12 . . 108.3(17) ?
C9 C26 H32 . . 112.7(13) ?
H13 C26 H32 . . 106.9(18) ?
H12 C26 H32 . . 106.3(18) ?
C11 C27 H8 . . 108.6(12) ?
C11 C27 H25 . . 112.4(13) ?
H8 C27 H25 . . 106.6(17) ?
C11 C27 H24 . . 112.3(14) ?
H8 C27 H24 . . 107.2(18) ?
H25 C27 H24 . . 109.4(19) ?
C26 C9 C15 . . 111.81(14) ?
C26 C9 C19 . . 112.99(15) ?
C15 C9 C19 . . 108.88(13) ?
C26 C9 C25 . . 116.32(14) ?
C15 C9 C25 . . 105.25(13) ?
C19 C9 C25 . . 100.72(13) ?
C19 C10 C20 . . 109.33(15) ?
C19 C10 H14 . . 110.4(11) ?
C20 C10 H14 . . 110.2(11) ?
C19 C10 H15 . . 111.7(11) ?
C20 C10 H15 . . 109.0(11) ?
H14 C10 H15 . . 106.2(15) ?
C27 C11 C12 . . 110.87(14) ?
C27 C11 C13 . . 110.55(14) ?
C12 C11 C13 . . 96.78(13) ?
C27 C11 C21 . . 116.44(15) ?
C12 C11 C21 . . 105.47(13) ?
C13 C11 C21 . . 114.75(13) ?
O6 C12 C11 . . 114.03(14) ?
O6 C12 C25 . . 113.82(13) ?
C11 C12 C25 . . 101.39(13) ?
O6 C12 C16 . . 115.02(13) ?
C11 C12 C16 . . 104.42(13) ?
C25 C12 C16 . . 106.83(13) ?
O8 C13 C15 . . 105.92(14) ?
O8 C13 C11 . . 101.41(13) ?
C15 C13 C11 . . 115.70(14) ?
O8 C13 H9 . . 106.5(10) ?
C15 C13 H9 . . 112.8(10) ?
C11 C13 H9 . . 113.1(10) ?
O2 C14 C25 . . 114.31(14) ?
O2 C14 C21 . . 113.86(14) ?
C25 C14 C21 . . 106.95(13) ?
O2 C14 H2 . . 106.6(10) ?
C25 C14 H2 . . 107.0(10) ?
C21 C14 H2 . . 107.7(10) ?
C13 C15 C9 . . 110.65(14) ?
C13 C15 H11 . . 108.1(10) ?
C9 C15 H11 . . 109.1(11) ?
C13 C15 H10 . . 111.9(11) ?
C9 C15 H10 . . 107.2(10) ?
H11 C15 H10 . . 109.9(14) ?
O8 C16 C23 . . 107.06(13) ?
O8 C16 C19 . . 106.73(13) ?
C23 C16 C19 . . 111.93(15) ?
O8 C16 C12 . . 104.10(13) ?
C23 C16 C12 . . 122.17(15) ?
C19 C16 C12 . . 103.74(13) ?
C18 C17 H7 . . 110.5(12) ?
C18 C17 H6 . . 111.3(11) ?
H7 C17 H6 . . 105.4(17) ?
C18 C17 H30 . . 112.4(12) ?
H7 C17 H30 . . 107.1(16) ?
H6 C17 H30 . . 109.9(16) ?
C24 C18 C17 . . 109.15(15) ?
C24 C18 C21 . . 113.24(15) ?
C17 C18 C21 . . 111.96(14) ?
C24 C18 H1 . . 109.0(10) ?
C17 C18 H1 . . 105.9(10) ?
C21 C18 H1 . . 107.3(10) ?
O5 C19 C10 . . 108.62(14) ?
O5 C19 C16 . . 106.20(13) ?
C10 C19 C16 . . 111.19(14) ?
O5 C19 C9 . . 108.43(13) ?
C10 C19 C9 . . 120.37(14) ?
C16 C19 C9 . . 101.06(13) ?
C10 C20 C22 . . 112.44(16) ?
C10 C20 H17 . . 109.5(11) ?
C22 C20 H17 . . 109.4(11) ?
C10 C20 H16 . . 109.7(11) ?
C22 C20 H16 . . 108.0(11) ?
H17 C20 H16 . . 107.7(16) ?
O1 C21 C18 . . 109.33(14) ?
O1 C21 C11 . . 104.10(13) ?
C18 C21 C11 . . 117.15(14) ?
O1 C21 C14 . . 108.40(13) ?
C18 C21 C14 . . 112.99(14) ?
C11 C21 C14 . . 104.22(13) ?
C20 C22 C23 . . 113.48(15) ?
C20 C22 H18 . . 108.6(10) ?
C23 C22 H18 . . 108.1(11) ?
C20 C22 H23 . . 110.9(11) ?
C23 C22 H23 . . 109.6(11) ?
H18 C22 H23 . . 105.8(15) ?
C16 C23 C22 . . 109.44(15) ?
C16 C23 H20 . . 108.1(11) ?
C22 C23 H20 . . 109.8(11) ?
C16 C23 H19 . . 109.8(11) ?
C22 C23 H19 . . 111.8(11) ?
H20 C23 H19 . . 107.8(15) ?
C18 C24 H3 . . 111.9(10) ?
C18 C24 H4 . . 110.0(11) ?
H3 C24 H4 . . 108.6(15) ?
C18 C24 H5 . . 108.1(11) ?
H3 C24 H5 . . 109.6(15) ?
H4 C24 H5 . . 108.6(16) ?
O3 C25 C14 . . 106.99(13) ?
O3 C25 C12 . . 112.51(13) ?
C14 C25 C12 . . 106.24(13) ?
O3 C25 C9 . . 113.88(13) ?
C14 C25 C9 . . 115.92(14) ?
C12 C25 C9 . . 101.08(13) ?
H21 O9W H22 . . 109.(2) ?