# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_su61
_database_code_depnum_ccdc_archive 'CCDC 1043689'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 O5'
_chemical_formula_weight         224.21

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

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                   12.939(3)
_cell_length_b                   6.3984(13)
_cell_length_c                   11.757(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.899(5)
_cell_angle_gamma                90.00
_cell_volume                     969.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    1797
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      28.24

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   'empirical (SADABS)'
_exptl_absorpt_correction_T_min  0.707908
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(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  'CCD area detector'
_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            6980
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2402
_reflns_number_gt                1969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0780P)²+0.1882P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 0.27536(12) -0.1896(2) 0.21152(13) 0.0170(3) Uani 1 1 d . . .
H1A H 0.2414 -0.3088 0.1696 0.020 Uiso 1 1 calc R . .
H1B H 0.3279 -0.2457 0.2698 0.020 Uiso 1 1 calc R . .
C2 C 0.32827(11) -0.0464(2) 0.12759(12) 0.0135(3) Uani 1 1 d . . .
C3 C 0.44487(11) -0.0147(3) 0.15053(13) 0.0176(3) Uani 1 1 d . . .
H3A H 0.4654 -0.0140 0.2336 0.021 Uiso 1 1 calc R . .
H3B H 0.4833 -0.1273 0.1146 0.021 Uiso 1 1 calc R . .
C4 C 0.37389(11) 0.3123(2) 0.09590(14) 0.0161(3) Uani 1 1 d . . .
H4A H 0.3505 0.3481 0.0159 0.019 Uiso 1 1 calc R . .
H4B H 0.3873 0.4434 0.1394 0.019 Uiso 1 1 calc R . .
C5 C 0.29299(11) 0.1818(2) 0.14879(12) 0.0133(3) Uani 1 1 d . . .
C6 C 0.17846(11) 0.1938(2) 0.12093(12) 0.0133(3) Uani 1 1 d . . .
C7 C 0.10316(11) 0.3134(2) 0.04300(14) 0.0163(3) Uani 1 1 d . . .
H7A H 0.1083 0.4652 0.0586 0.020 Uiso 1 1 calc R . .
H7B H 0.1149 0.2878 -0.0379 0.020 Uiso 1 1 calc R . .
C8 C 0.01622(11) 0.0851(2) 0.15525(13) 0.0170(3) Uani 1 1 d . . .
C9 C 0.12792(11) 0.0609(2) 0.18316(13) 0.0145(3) Uani 1 1 d . . .
C10 C 0.19465(11) -0.0621(2) 0.26924(13) 0.0160(3) Uani 1 1 d . . .
H10 H 0.1514 -0.1545 0.3148 0.019 Uiso 1 1 calc R . .
C11 C 0.29999(12) -0.1095(2) 0.00347(13) 0.0169(3) Uani 1 1 d . . .
H11A H 0.3285 -0.0072 -0.0474 0.025 Uiso 1 1 calc R . .
H11B H 0.2243 -0.1141 -0.0115 0.025 Uiso 1 1 calc R . .
H11C H 0.3289 -0.2479 -0.0103 0.025 Uiso 1 1 calc R . .
O1 O 0.46570(8) 0.18532(18) 0.10054(10) 0.0190(3) Uani 1 1 d . . .
O2 O 0.00327(7) 0.23157(18) 0.06961(9) 0.0169(3) Uani 1 1 d . . .
O3 O -0.05705(8) 0.00298(19) 0.19321(10) 0.0231(3) Uani 1 1 d . . .
O4 O 0.24995(8) 0.09115(19) 0.34167(9) 0.0192(3) Uani 1 1 d . . .
O5 O 0.31213(8) 0.22842(18) 0.27037(9) 0.0166(3) Uani 1 1 d . . .


_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
C1 C10 1.529(2) . ?
C1 C2 1.549(2) . ?
C2 C3 1.523(2) . ?
C2 C11 1.528(2) . ?
C2 C5 1.556(2) . ?
C3 O1 1.4435(19) . ?
C4 O1 1.4364(18) . ?
C4 C5 1.514(2) . ?
C5 O5 1.4605(17) . ?
C5 C6 1.492(2) . ?
C6 C9 1.330(2) . ?
C6 C7 1.490(2) . ?
C7 O2 1.4531(17) . ?
C8 O3 1.2025(18) . ?
C8 O2 1.3754(19) . ?
C8 C9 1.463(2) . ?
C9 C10 1.497(2) . ?
C10 O4 1.4473(19) . ?
O4 O5 1.4955(15) . ?

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
C10 C1 C2 108.84(12) . . ?
C3 C2 C11 110.92(12) . . ?
C3 C2 C1 116.80(12) . . ?
C11 C2 C1 111.65(12) . . ?
C3 C2 C5 98.44(12) . . ?
C11 C2 C5 110.58(12) . . ?
C1 C2 C5 107.55(11) . . ?
O1 C3 C2 105.20(12) . . ?
O1 C4 C5 105.71(12) . . ?
O5 C5 C6 106.65(11) . . ?
O5 C5 C4 102.93(11) . . ?
C6 C5 C4 126.16(12) . . ?
O5 C5 C2 108.72(11) . . ?
C6 C5 C2 108.23(12) . . ?
C4 C5 C2 103.25(11) . . ?
C9 C6 C7 109.88(13) . . ?
C9 C6 C5 111.84(13) . . ?
C7 C6 C5 138.27(13) . . ?
O2 C7 C6 103.27(12) . . ?
O3 C8 O2 121.25(13) . . ?
O3 C8 C9 131.75(15) . . ?
O2 C8 C9 107.00(12) . . ?
C6 C9 C8 109.39(14) . . ?
C6 C9 C10 115.22(13) . . ?
C8 C9 C10 135.16(13) . . ?
O4 C10 C9 105.60(13) . . ?
O4 C10 C1 107.50(12) . . ?
C9 C10 C1 110.91(12) . . ?
C4 O1 C3 109.55(11) . . ?
C8 O2 C7 110.37(11) . . ?
C10 O4 O5 109.32(10) . . ?
C5 O5 O4 111.97(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.063
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1043693'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.34

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.6489(7)
_cell_length_b                   9.9633(5)
_cell_length_c                   20.3053(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.2010(12)
_cell_angle_gamma                90
_cell_volume                     3180.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.3036
_cell_measurement_theta_max      25.0426
_cell_measurement_temperature    93.0(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    0.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            21783
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             5561
_reflns_number_gt                4730
_reflns_threshold_expression     'I > 2s(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0921
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         5561
_refine_ls_number_parameters     423
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[s²(Fo²)+(0.0392P)²+1.5229P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.210
_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'
N N 0.0061 0.0033 '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 Instrument Service v3.0.29'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruke 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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.09814(9) 0.00235(15) 0.14805(8) 0.0189(3) Uani d . . . 1 A 1
C C2 -0.04404(9) 0.11924(15) 0.17497(7) 0.0159(3) Uani d . . . 1 A 1
C C3 0.00979(9) 0.20856(15) 0.14708(7) 0.0158(3) Uani d . . . 1 A 1
H H3 0.0034 0.1872 0.0975 0.019 Uiso calc U . R 1 A 1
C C7 -0.00955(9) 0.35719(15) 0.15670(7) 0.0183(3) Uani d . . . 1 A 1
H H7A -0.0645 0.3827 0.1217 0.022 Uiso calc U . R 1 A 1
H H7B 0.0354 0.4146 0.1496 0.022 Uiso calc U . R 1 A 1
C C8 -0.01361(9) 0.37916(15) 0.23092(8) 0.0185(3) Uani d . . . 1 A 1
C C9 0.04746(10) 0.48118(16) 0.27712(8) 0.0227(3) Uani d . . . 1 A 1
H H9A 0.1029 0.4792 0.269 0.027 Uiso calc U . R 1 A 1
H H9B 0.0237 0.573 0.2678 0.027 Uiso calc U . R 1 A 1
C C10 0.04565(10) 0.29759(15) 0.34857(8) 0.0201(3) Uani d . . . 1 A 1
H H10A -0.0001 0.2754 0.3679 0.024 Uiso calc U . R 1 A 1
H H10B 0.0989 0.2539 0.3777 0.024 Uiso calc U . R 1 A 1
C C11 0.02203(9) 0.25101(15) 0.27361(8) 0.0170(3) Uani d . . . 1 A 1
C C12 -0.03521(9) 0.13664(15) 0.24182(7) 0.0167(3) Uani d . . . 1 A 1
C C13 -0.08610(10) 0.03387(16) 0.26427(8) 0.0230(3) Uani d . . . 1 A 1
H H13A -0.0493 -0.0219 0.3028 0.028 Uiso calc U . R 1 A 1
H H13B -0.1307 0.0766 0.2796 0.028 Uiso calc U . R 1 A 1
C C14 -0.10437(10) 0.40720(17) 0.22993(8) 0.0246(4) Uani d . . . 1 A 1
H H14A -0.1055 0.4095 0.2779 0.037 Uiso calc U . R 1 A 1
H H14B -0.1423 0.3361 0.2039 0.037 Uiso calc U . R 1 A 1
H H14C -0.1234 0.4939 0.2074 0.037 Uiso calc U . R 1 A 1
C C15 0.12847(9) 0.04944(15) 0.19732(7) 0.0171(3) Uani d . . . 1 B 1
C C16 0.12580(9) -0.13929(15) 0.11921(8) 0.0193(3) Uani d . . . 1 C 1
C C17 0.08201(10) -0.15222(17) 0.04122(8) 0.0240(4) Uani d . . . 1 C 1
H H17A 0.0209 -0.136 0.0301 0.036 Uiso calc U . R 1 C 1
H H17B 0.091 -0.2428 0.0262 0.036 Uiso calc U . R 1 C 1
H H17C 0.1058 -0.0862 0.017 0.036 Uiso calc U . R 1 C 1
C C18 0.08816(11) -0.23691(17) 0.15880(9) 0.0266(4) Uani d . . . 1 C 1
H H18A 0.1187 -0.2288 0.2089 0.04 Uiso calc U . R 1 C 1
H H18B 0.0937 -0.3288 0.1436 0.04 Uiso calc U . R 1 C 1
H H18C 0.0279 -0.216 0.1493 0.04 Uiso calc U . R 1 C 1
C C19 0.22094(10) -0.15359(17) 0.13817(9) 0.0266(4) Uani d . . . 1 C 1
H H19A 0.2426 -0.0838 0.1144 0.04 Uiso calc U . R 1 C 1
H H19B 0.2344 -0.2422 0.1236 0.04 Uiso calc U . R 1 C 1
H H19C 0.2476 -0.144 0.1887 0.04 Uiso calc U . R 1 C 1
C C20 0.12581(9) -0.11123(15) 0.57732(7) 0.0180(3) Uani d . . . 1 D 1
C C21 0.16779(9) -0.07702(15) 0.52632(7) 0.0163(3) Uani d . . . 1 D 1
C C22 0.14748(9) 0.01441(15) 0.46460(7) 0.0163(3) Uani d . . . 1 D 1
H H22 0.0897 0.0553 0.4535 0.02 Uiso calc U . R 1 D 1
C C23 0.15849(9) -0.05851(16) 0.40121(7) 0.0186(3) Uani d . . . 1 D 1
H H23A 0.1591 0.0078 0.3651 0.022 Uiso calc U . R 1 D 1
H H23B 0.1101 -0.1204 0.3809 0.022 Uiso calc U . R 1 D 1
C C24 0.24263(9) -0.13839(15) 0.42403(8) 0.0192(3) Uani d . . . 1 D 1
C C25 0.30819(9) -0.10207(18) 0.38919(8) 0.0235(4) Uani d . . . 1 D 1
H H25A 0.2975 -0.1526 0.3452 0.028 Uiso calc U . R 1 D 1
H H25B 0.3065 -0.0048 0.3789 0.028 Uiso calc U . R 1 D 1
C C26 0.38331(9) -0.13732(17) 0.50809(8) 0.0218(3) Uani d . . . 1 D 1
H H26A 0.425 -0.0735 0.5382 0.026 Uiso calc U . R 1 D 1
H H26B 0.3945 -0.2277 0.5295 0.026 Uiso calc U . R 1 D 1
C C27 0.29371(9) -0.09350(15) 0.49933(8) 0.0174(3) Uani d . . . 1 D 1
C C28 0.24512(9) -0.13058(14) 0.54651(7) 0.0168(3) Uani d . . . 1 D 1
C C29 0.25912(9) -0.21120(16) 0.61092(8) 0.0209(3) Uani d . . . 1 D 1
H H29A 0.268 -0.3071 0.6026 0.025 Uiso calc U . R 1 D 1
H H29B 0.3089 -0.1778 0.6493 0.025 Uiso calc U . R 1 D 1
C C31 0.12155(10) 0.32847(16) 0.58520(9) 0.0247(4) Uani d . . . 1 D 1
C C35 0.22712(10) -0.29024(17) 0.42003(9) 0.0277(4) Uani d . . . 1 D 1
H H35A 0.1979 -0.3162 0.3715 0.042 Uiso calc U . R 1 D 1
H H35B 0.1918 -0.3143 0.4485 0.042 Uiso calc U . R 1 D 1
H H35C 0.2817 -0.3373 0.4376 0.042 Uiso calc U . R 1 D 1
C C36 0.22006(9) 0.20307(15) 0.54071(7) 0.0169(3) Uani d . . . 1 D 1
C C37 0.02604(11) 0.31412(19) 0.56654(10) 0.0356(4) Uani d . . . 1 D 1
H H37A -0.0014 0.3339 0.5169 0.053 Uiso calc U . R 1 D 1
H H37B 0.0054 0.3771 0.5944 0.053 Uiso calc U . R 1 D 1
H H37C 0.0123 0.2221 0.5762 0.053 Uiso calc U . R 1 D 1
C C38 0.16611(12) 0.2922(2) 0.66086(9) 0.0372(4) Uani d . . . 1 D 1
H H38A 0.1585 0.1963 0.6677 0.056 Uiso calc U . R 1 D 1
H H38B 0.1418 0.3446 0.6905 0.056 Uiso calc U . R 1 D 1
H H38C 0.2269 0.3123 0.6733 0.056 Uiso calc U . R 1 D 1
C C39 0.14611(12) 0.46513(18) 0.56593(11) 0.0375(4) Uani d . . . 1 D 1
H H39A 0.2079 0.4693 0.5768 0.056 Uiso calc U . R 1 D 1
H H39B 0.1282 0.5342 0.5925 0.056 Uiso calc U . R 1 D 1
H H39C 0.1181 0.4806 0.5159 0.056 Uiso calc U . R 1 D 1
N N1 0.09808(7) 0.18293(13) 0.19494(6) 0.0164(3) Uani d . . . 1 . .
N N2 0.21606(7) 0.11785(12) 0.48490(6) 0.0162(3) Uani d . . . 1 D 1
O O1 -0.12020(6) -0.05188(11) 0.09212(5) 0.0231(3) Uani d . . . 1 . .
O O2 -0.12327(7) -0.04536(11) 0.20189(5) 0.0253(3) Uani d . . . 1 . .
O O3 0.05688(7) 0.44064(11) 0.34720(5) 0.0245(3) Uani d . . . 1 . .
O O4 0.10505(6) 0.22390(10) 0.26451(5) 0.0179(2) Uani d . . . 1 . .
O O5 0.17324(7) -0.00385(11) 0.24939(5) 0.0264(3) Uani d . . . 1 . .
O O6 0.10322(6) 0.00089(10) 0.13268(5) 0.0180(2) Uani d . . . 1 . .
O O7 0.05778(6) -0.08055(11) 0.58128(5) 0.0238(3) Uani d . . . 1 D 1
O O8 0.18092(6) -0.19190(11) 0.62668(5) 0.0223(2) Uani d . . . 1 D 1
O O9 0.38915(6) -0.13922(12) 0.43939(6) 0.0279(3) Uani d . . . 1 D 1
O O12 0.29785(6) 0.05526(10) 0.49794(5) 0.0187(2) Uani d . . . 1 D 1
O O13 0.28423(6) 0.25077(11) 0.57997(6) 0.0233(3) Uani d . . . 1 D 1
O O14 0.14026(6) 0.22687(11) 0.53910(5) 0.0215(2) Uani d . . . 1 D 1


_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
C1 O1 . 1.2009(18) ?
C1 O2 . 1.3773(18) ?
C1 C2 . 1.464(2) ?
C2 C12 . 1.328(2) ?
C2 C3 . 1.500(2) ?
C3 N1 . 1.4935(18) ?
C3 C7 . 1.541(2) ?
C3 H3 . 1.0 ?
C7 C8 . 1.546(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.523(2) ?
C8 C14 . 1.530(2) ?
C8 C11 . 1.548(2) ?
C9 O3 . 1.4373(19) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 O3 . 1.4389(19) ?
C10 C11 . 1.514(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 O4 . 1.4785(17) ?
C11 C12 . 1.490(2) ?
C12 C13 . 1.493(2) ?
C13 O2 . 1.4474(18) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 O5 . 1.1987(18) ?
C15 O6 . 1.3307(18) ?
C15 N1 . 1.418(2) ?
C16 O6 . 1.4947(18) ?
C16 C19 . 1.509(2) ?
C16 C17 . 1.515(2) ?
C16 C18 . 1.522(2) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 O7 . 1.2011(18) ?
C20 O8 . 1.3738(18) ?
C20 C21 . 1.467(2) ?
C21 C28 . 1.328(2) ?
C21 C22 . 1.495(2) ?
C22 N2 . 1.4921(19) ?
C22 C23 . 1.541(2) ?
C22 H22 . 1.0 ?
C23 C24 . 1.544(2) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.527(2) ?
C24 C35 . 1.532(2) ?
C24 C27 . 1.551(2) ?
C25 O9 . 1.4455(18) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 O9 . 1.4301(18) ?
C26 C27 . 1.508(2) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 O12 . 1.4845(18) ?
C27 C28 . 1.489(2) ?
C28 C29 . 1.487(2) ?
C29 O8 . 1.4521(17) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C31 O14 . 1.4799(18) ?
C31 C39 . 1.510(3) ?
C31 C38 . 1.514(2) ?
C31 C37 . 1.515(2) ?
C35 H35A . 0.98 ?
C35 H35B . 0.98 ?
C35 H35C . 0.98 ?
C36 O13 . 1.2011(18) ?
C36 O14 . 1.3394(17) ?
C36 N2 . 1.4001(19) ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
N1 O4 . 1.4379(15) ?
N2 O12 . 1.4408(15) ?

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
O1 C1 O2 . . 121.13(14) ?
O1 C1 C2 . . 132.10(14) ?
O2 C1 C2 . . 106.76(12) ?
C12 C2 C1 . . 109.47(13) ?
C12 C2 C3 . . 115.44(13) ?
C1 C2 C3 . . 134.57(13) ?
N1 C3 C2 . . 103.60(11) ?
N1 C3 C7 . . 106.48(11) ?
C2 C3 C7 . . 110.27(12) ?
N1 C3 H3 . . 112.0 ?
C2 C3 H3 . . 112.0 ?
C7 C3 H3 . . 112.0 ?
C3 C7 C8 . . 109.72(12) ?
C3 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
C3 C7 H7B . . 109.7 ?
C8 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C9 C8 C14 . . 110.03(12) ?
C9 C8 C7 . . 117.42(12) ?
C14 C8 C7 . . 111.87(12) ?
C9 C8 C11 . . 98.64(12) ?
C14 C8 C11 . . 110.66(12) ?
C7 C8 C11 . . 107.31(12) ?
O3 C9 C8 . . 104.81(12) ?
O3 C9 H9A . . 110.8 ?
C8 C9 H9A . . 110.8 ?
O3 C9 H9B . . 110.8 ?
C8 C9 H9B . . 110.8 ?
H9A C9 H9B . . 108.9 ?
O3 C10 C11 . . 106.05(12) ?
O3 C10 H10A . . 110.5 ?
C11 C10 H10A . . 110.5 ?
O3 C10 H10B . . 110.5 ?
C11 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.7 ?
O4 C11 C12 . . 107.29(11) ?
O4 C11 C10 . . 103.72(11) ?
C12 C11 C10 . . 126.00(12) ?
O4 C11 C8 . . 106.42(11) ?
C12 C11 C8 . . 108.40(12) ?
C10 C11 C8 . . 103.60(12) ?
C2 C12 C11 . . 112.52(13) ?
C2 C12 C13 . . 109.85(13) ?
C11 C12 C13 . . 137.64(13) ?
O2 C13 C12 . . 103.25(11) ?
O2 C13 H13A . . 111.1 ?
C12 C13 H13A . . 111.1 ?
O2 C13 H13B . . 111.1 ?
C12 C13 H13B . . 111.1 ?
H13A C13 H13B . . 109.1 ?
C8 C14 H14A . . 109.5 ?
C8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O5 C15 O6 . . 127.73(14) ?
O5 C15 N1 . . 123.84(13) ?
O6 C15 N1 . . 108.30(12) ?
O6 C16 C19 . . 110.34(12) ?
O6 C16 C17 . . 101.95(12) ?
C19 C16 C17 . . 111.25(12) ?
O6 C16 C18 . . 109.17(12) ?
C19 C16 C18 . . 112.64(13) ?
C17 C16 C18 . . 110.95(13) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O7 C20 O8 . . 121.21(13) ?
O7 C20 C21 . . 131.80(14) ?
O8 C20 C21 . . 106.98(12) ?
C28 C21 C20 . . 109.10(13) ?
C28 C21 C22 . . 115.63(13) ?
C20 C21 C22 . . 134.76(13) ?
N2 C22 C21 . . 104.34(11) ?
N2 C22 C23 . . 105.43(11) ?
C21 C22 C23 . . 110.90(12) ?
N2 C22 H22 . . 111.9 ?
C21 C22 H22 . . 111.9 ?
C23 C22 H22 . . 111.9 ?
C22 C23 C24 . . 109.75(11) ?
C22 C23 H23A . . 109.7 ?
C24 C23 H23A . . 109.7 ?
C22 C23 H23B . . 109.7 ?
C24 C23 H23B . . 109.7 ?
H23A C23 H23B . . 108.2 ?
C25 C24 C35 . . 110.07(13) ?
C25 C24 C23 . . 117.07(13) ?
C35 C24 C23 . . 111.88(13) ?
C25 C24 C27 . . 98.32(12) ?
C35 C24 C27 . . 111.41(13) ?
C23 C24 C27 . . 107.24(11) ?
O9 C25 C24 . . 104.81(12) ?
O9 C25 H25A . . 110.8 ?
C24 C25 H25A . . 110.8 ?
O9 C25 H25B . . 110.8 ?
C24 C25 H25B . . 110.8 ?
H25A C25 H25B . . 108.9 ?
O9 C26 C27 . . 105.72(12) ?
O9 C26 H26A . . 110.6 ?
C27 C26 H26A . . 110.6 ?
O9 C26 H26B . . 110.6 ?
C27 C26 H26B . . 110.6 ?
H26A C26 H26B . . 108.7 ?
O12 C27 C28 . . 107.36(11) ?
O12 C27 C26 . . 103.95(12) ?
C28 C27 C26 . . 125.30(13) ?
O12 C27 C24 . . 106.44(11) ?
C28 C27 C24 . . 108.96(12) ?
C26 C27 C24 . . 103.49(12) ?
C21 C28 C29 . . 110.14(12) ?
C21 C28 C27 . . 112.23(13) ?
C29 C28 C27 . . 137.63(13) ?
O8 C29 C28 . . 103.29(11) ?
O8 C29 H29A . . 111.1 ?
C28 C29 H29A . . 111.1 ?
O8 C29 H29B . . 111.1 ?
C28 C29 H29B . . 111.1 ?
H29A C29 H29B . . 109.1 ?
O14 C31 C39 . . 108.76(13) ?
O14 C31 C38 . . 110.11(13) ?
C39 C31 C38 . . 113.23(15) ?
O14 C31 C37 . . 101.48(12) ?
C39 C31 C37 . . 111.81(15) ?
C38 C31 C37 . . 110.79(15) ?
C24 C35 H35A . . 109.5 ?
C24 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C24 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
O13 C36 O14 . . 127.23(14) ?
O13 C36 N2 . . 124.91(13) ?
O14 C36 N2 . . 107.75(12) ?
C31 C37 H37A . . 109.5 ?
C31 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C31 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C31 C38 H38A . . 109.5 ?
C31 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C31 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C31 C39 H39A . . 109.5 ?
C31 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C31 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C15 N1 O4 . . 108.67(11) ?
C15 N1 C3 . . 116.51(11) ?
O4 N1 C3 . . 109.57(10) ?
C36 N2 O12 . . 108.86(10) ?
C36 N2 C22 . . 118.09(11) ?
O12 N2 C22 . . 110.06(10) ?
C1 O2 C13 . . 110.63(11) ?
C9 O3 C10 . . 108.96(11) ?
N1 O4 C11 . . 113.45(10) ?
C15 O6 C16 . . 120.22(11) ?
C20 O8 C29 . . 110.41(11) ?
C26 O9 C25 . . 109.73(10) ?
N2 O12 C27 . . 112.87(10) ?
C36 O14 C31 . . 121.27(11) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_audit_block_doi                 10.5517/cc148g1x
_database_code_depnum_ccdc_archive 'CCDC 1050808'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         226.22

_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                   24.3516(13)
_cell_length_b                   7.9830(4)
_cell_length_c                   10.7485(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.3458(14)
_cell_angle_gamma                90
_cell_volume                     2048.66(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9599
_cell_measurement_theta_min      2.6903
_cell_measurement_theta_max      25.0614
_cell_measurement_temperature    93.0(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960

_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            14197
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3618
_reflns_number_gt                3289
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0890
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+1.2306P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(5)

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 Instrument Service v3.0.29'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruke 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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.28030(6) 0.13832(19) 0.22110(14) 0.0207(3) Uani d . . . 1 . .
H H1A 0.2841 0.2342 0.1665 0.031 Uiso calc U . R 1 . .
H H1B 0.2432 0.1404 0.2435 0.031 Uiso calc U . R 1 . .
H H1C 0.2848 0.0341 0.1759 0.031 Uiso calc U . R 1 . .
C C2 0.32561(6) 0.14809(17) 0.34253(13) 0.0147(3) Uani d . . . 1 . .
C C3 0.32525(6) 0.32318(18) 0.40077(14) 0.0190(3) Uani d . . . 1 . .
H H3A 0.2866 0.3593 0.4031 0.023 Uiso calc U . R 1 . .
H H3B 0.3479 0.3256 0.488 0.023 Uiso calc U . R 1 . .
C C4 0.39477(6) 0.33479(17) 0.28178(14) 0.0163(3) Uani d . . . 1 . .
H H4A 0.4313 0.3694 0.3334 0.02 Uiso calc U . R 1 . .
H H4B 0.3956 0.3522 0.191 0.02 Uiso calc U . R 1 . .
C C5 0.38255(6) 0.15500(17) 0.30685(12) 0.0134(3) Uani d . . . 1 . .
C C6 0.41612(6) 0.02389(17) 0.31140(12) 0.0130(3) Uani d . . . 1 . .
C C7 0.47395(6) 0.01632(18) 0.28477(13) 0.0174(3) Uani d . . . 1 . .
H H7A 0.473 -0.0107 0.1945 0.021 Uiso calc U . R 1 . .
H H7B 0.4936 0.1243 0.3052 0.021 Uiso calc U . R 1 . .
C C8 0.46365(6) -0.20416(17) 0.41972(13) 0.0167(3) Uani d . . . 1 . .
C C9 0.37143(6) -0.10876(17) 0.47664(12) 0.0142(3) Uani d . . . 1 . .
H H9 0.3964 -0.0529 0.5499 0.017 Uiso calc U . R 1 . .
C C10 0.31942(6) 0.00043(17) 0.43138(13) 0.0165(3) Uani d . . . 1 . .
H H10A 0.3073 0.0461 0.5072 0.02 Uiso calc U . R 1 . .
H H10B 0.289 -0.0729 0.3871 0.02 Uiso calc U . R 1 . .
C C11 0.40405(6) -0.13815(16) 0.37039(12) 0.0134(3) Uani d . . . 1 . .
C C12 0.22802(6) 0.84221(19) 0.68162(14) 0.0207(3) Uani d . . . 1 . .
H H12A 0.2279 0.9352 0.741 0.031 Uiso calc U . R 1 . .
H H12B 0.2615 0.8493 0.6442 0.031 Uiso calc U . R 1 . .
H H12C 0.2281 0.7357 0.727 0.031 Uiso calc U . R 1 . .
C C13 0.17549(6) 0.85222(17) 0.57594(12) 0.0143(3) Uani d . . . 1 . .
C C14 0.17239(7) 0.69712(18) 0.49138(14) 0.0206(3) Uani d . . . 1 . .
H H14A 0.1451 0.714 0.4111 0.025 Uiso calc U . R 1 . .
H H14B 0.2095 0.6719 0.4712 0.025 Uiso calc U . R 1 . .
C C15 0.11598(6) 0.63401(17) 0.63694(13) 0.0179(3) Uani d . . . 1 . .
H H15A 0.1245 0.593 0.7256 0.021 Uiso calc U . R 1 . .
H H15B 0.0769 0.6035 0.5985 0.021 Uiso calc U . R 1 . .
C C16 0.12426(6) 0.82028(17) 0.63245(12) 0.0135(3) Uani d . . . 1 . .
C C17 0.09124(6) 0.94221(17) 0.65752(12) 0.0138(3) Uani d . . . 1 . .
C C18 0.03756(6) 0.92981(18) 0.70526(13) 0.0176(3) Uani d . . . 1 . .
H H18A 0.0173 0.8253 0.6753 0.021 Uiso calc U . R 1 . .
H H18B 0.0448 0.9321 0.7992 0.021 Uiso calc U . R 1 . .
C C19 0.03755(6) 1.18601(18) 0.60129(12) 0.0157(3) Uani d . . . 1 . .
C C20 0.11702(6) 1.11138(17) 0.48624(12) 0.0126(3) Uani d . . . 1 . .
H H20 0.0892 1.044 0.4257 0.015 Uiso calc U . R 1 . .
C C21 0.17353(5) 1.02144(17) 0.50540(12) 0.0139(3) Uani d . . . 1 . .
H H21A 0.2026 1.0961 0.5537 0.017 Uiso calc U . R 1 . .
H H21B 0.1831 1.0017 0.4213 0.017 Uiso calc U . R 1 . .
C C22 0.09756(5) 1.11884(17) 0.61354(12) 0.0133(3) Uani d . . . 1 . .
O O1 0.34963(4) 0.42807(12) 0.31733(9) 0.0191(2) Uani d . . . 1 . .
O O2 0.35362(4) -0.26590(12) 0.51635(9) 0.0193(2) Uani d . . . 1 . .
H H2 0.3635 -0.2746 0.5955 0.029 Uiso calc U . R 1 . .
O O3 0.37580(4) -0.25254(12) 0.27795(9) 0.0169(2) Uani d . . . 1 . .
H H3 0.3664 -0.3379 0.3144 0.025 Uiso calc U . R 1 . .
O O4 0.47829(4) -0.31690(13) 0.49233(10) 0.0252(3) Uani d . . . 1 . .
O O5 0.50134(4) -0.11703(13) 0.36735(9) 0.0195(2) Uani d . . . 1 . .
O O6 0.15465(5) 0.56401(12) 0.56451(9) 0.0229(3) Uani d . . . 1 . .
O O7 0.12058(4) 1.27296(12) 0.43278(9) 0.0165(2) Uani d . . . 1 . .
H H7 0.1335 1.3413 0.4906 0.025 Uiso calc U . R 1 . .
O O8 0.13572(4) 1.22516(12) 0.69368(9) 0.0162(2) Uani d . . . 1 . .
H H8 0.1302 1.2185 0.7683 0.024 Uiso calc U . R 1 . .
O O9 0.01891(4) 1.31607(13) 0.55608(10) 0.0225(2) Uani d . . . 1 . .
O O10 0.00553(4) 1.07657(12) 0.65241(9) 0.0188(2) Uani d . . . 1 . .


_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
C1 C2 . 1.5364(19) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C5 . 1.5104(18) ?
C2 C3 . 1.5322(19) ?
C2 C10 . 1.5430(19) ?
C3 O1 . 1.4378(17) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 O1 . 1.4402(17) ?
C4 C5 . 1.5009(19) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.3231(19) ?
C6 C7 . 1.4923(19) ?
C6 C11 . 1.4950(18) ?
C7 O5 . 1.4605(16) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 O4 . 1.1986(17) ?
C8 O5 . 1.3588(18) ?
C8 C11 . 1.5372(19) ?
C9 O2 . 1.4201(17) ?
C9 C11 . 1.5320(19) ?
C9 C10 . 1.5356(19) ?
C9 H9 . 1.0 ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 O3 . 1.4231(16) ?
C12 C13 . 1.5366(19) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C16 . 1.5128(19) ?
C13 C14 . 1.5290(19) ?
C13 C21 . 1.5452(18) ?
C14 O6 . 1.4378(17) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 O6 . 1.4469(18) ?
C15 C16 . 1.5027(19) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.324(2) ?
C17 C18 . 1.4987(19) ?
C17 C22 . 1.5046(19) ?
C18 O10 . 1.4591(17) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 O9 . 1.1972(17) ?
C19 O10 . 1.3571(17) ?
C19 C22 . 1.5376(19) ?
C20 O7 . 1.4216(16) ?
C20 C21 . 1.5296(18) ?
C20 C22 . 1.5348(18) ?
C20 H20 . 1.0 ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 O8 . 1.4181(16) ?
O2 H2 . 0.84 ?
O3 H3 . 0.84 ?
O7 H7 . 0.84 ?
O8 H8 . 0.84 ?

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
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C5 C2 C3 . . 98.62(11) ?
C5 C2 C1 . . 109.14(11) ?
C3 C2 C1 . . 109.42(11) ?
C5 C2 C10 . . 113.04(11) ?
C3 C2 C10 . . 115.78(11) ?
C1 C2 C10 . . 110.22(11) ?
O1 C3 C2 . . 103.90(11) ?
O1 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
O1 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O1 C4 C5 . . 104.95(11) ?
O1 C4 H4A . . 110.8 ?
C5 C4 H4A . . 110.8 ?
O1 C4 H4B . . 110.8 ?
C5 C4 H4B . . 110.8 ?
H4A C4 H4B . . 108.8 ?
C6 C5 C4 . . 128.32(12) ?
C6 C5 C2 . . 123.58(12) ?
C4 C5 C2 . . 107.75(11) ?
C5 C6 C7 . . 128.65(13) ?
C5 C6 C11 . . 121.90(12) ?
C7 C6 C11 . . 108.54(11) ?
O5 C7 C6 . . 104.38(11) ?
O5 C7 H7A . . 110.9 ?
C6 C7 H7A . . 110.9 ?
O5 C7 H7B . . 110.9 ?
C6 C7 H7B . . 110.9 ?
H7A C7 H7B . . 108.9 ?
O4 C8 O5 . . 121.03(13) ?
O4 C8 C11 . . 128.44(13) ?
O5 C8 C11 . . 110.52(11) ?
O2 C9 C11 . . 108.82(11) ?
O2 C9 C10 . . 108.36(11) ?
C11 C9 C10 . . 111.53(11) ?
O2 C9 H9 . . 109.4 ?
C11 C9 H9 . . 109.4 ?
C10 C9 H9 . . 109.4 ?
C9 C10 C2 . . 117.05(11) ?
C9 C10 H10A . . 108.0 ?
C2 C10 H10A . . 108.0 ?
C9 C10 H10B . . 108.0 ?
C2 C10 H10B . . 108.0 ?
H10A C10 H10B . . 107.3 ?
O3 C11 C6 . . 111.56(10) ?
O3 C11 C9 . . 111.62(11) ?
C6 C11 C9 . . 110.96(11) ?
O3 C11 C8 . . 108.35(11) ?
C6 C11 C8 . . 101.06(11) ?
C9 C11 C8 . . 112.84(11) ?
C13 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C13 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C16 C13 C14 . . 98.86(11) ?
C16 C13 C12 . . 109.07(11) ?
C14 C13 C12 . . 109.50(12) ?
C16 C13 C21 . . 113.33(11) ?
C14 C13 C21 . . 115.03(11) ?
C12 C13 C21 . . 110.43(11) ?
O6 C14 C13 . . 104.99(11) ?
O6 C14 H14A . . 110.7 ?
C13 C14 H14A . . 110.7 ?
O6 C14 H14B . . 110.7 ?
C13 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.8 ?
O6 C15 C16 . . 105.03(11) ?
O6 C15 H15A . . 110.7 ?
C16 C15 H15A . . 110.7 ?
O6 C15 H15B . . 110.7 ?
C16 C15 H15B . . 110.7 ?
H15A C15 H15B . . 108.8 ?
C17 C16 C15 . . 129.09(13) ?
C17 C16 C13 . . 122.67(12) ?
C15 C16 C13 . . 107.83(11) ?
C16 C17 C18 . . 128.82(13) ?
C16 C17 C22 . . 121.43(12) ?
C18 C17 C22 . . 108.63(11) ?
O10 C18 C17 . . 104.42(11) ?
O10 C18 H18A . . 110.9 ?
C17 C18 H18A . . 110.9 ?
O10 C18 H18B . . 110.9 ?
C17 C18 H18B . . 110.9 ?
H18A C18 H18B . . 108.9 ?
O9 C19 O10 . . 121.36(13) ?
O9 C19 C22 . . 127.97(13) ?
O10 C19 C22 . . 110.66(11) ?
O7 C20 C21 . . 110.83(11) ?
O7 C20 C22 . . 112.29(10) ?
C21 C20 C22 . . 109.00(11) ?
O7 C20 H20 . . 108.2 ?
C21 C20 H20 . . 108.2 ?
C22 C20 H20 . . 108.2 ?
C20 C21 C13 . . 114.62(11) ?
C20 C21 H21A . . 108.6 ?
C13 C21 H21A . . 108.6 ?
C20 C21 H21B . . 108.6 ?
C13 C21 H21B . . 108.6 ?
H21A C21 H21B . . 107.6 ?
O8 C22 C17 . . 117.73(11) ?
O8 C22 C20 . . 106.52(10) ?
C17 C22 C20 . . 108.20(11) ?
O8 C22 C19 . . 109.97(11) ?
C17 C22 C19 . . 101.51(11) ?
C20 C22 C19 . . 113.09(11) ?
C3 O1 C4 . . 107.14(10) ?
C9 O2 H2 . . 109.5 ?
C11 O3 H3 . . 109.5 ?
C8 O5 C7 . . 111.09(10) ?
C14 O6 C15 . . 107.82(10) ?
C20 O7 H7 . . 109.5 ?
C22 O8 H8 . . 109.5 ?
C19 O10 C18 . . 111.65(10) ?

