# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_S-plus-2a
_database_code_depnum_ccdc_archive 'CCDC 1505596'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_audit_creation_date             2016-09-09
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H28 O4 Si'
_chemical_formula_moiety         'C17 H28 O4 Si'
_chemical_formula_weight         324.49
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.2037(11)
_cell_length_b                   10.9197(17)
_cell_length_c                   23.762(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1869.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1835
_cell_measurement_theta_min      39.90
_cell_measurement_theta_max      67.80
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704.00
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.918

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            19865
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_theta_max         68.058
_diffrn_reflns_theta_min         3.720
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3374
_reflns_number_gt                3219
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.989

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1337
_refine_ls_number_restraints     14
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     230
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0824P)²+0.1414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0183(18)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(16)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Si Si 0.2541 0.3302
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.23665(12) 0.43404(7) 0.07973(3) 0.0522(3) Uani 1 1 d . . . . .
O1 O 0.2930(2) 0.48475(16) 0.14377(7) 0.0458(5) Uani 1 1 d . . . . .
O2 O 0.4642(3) 0.68896(19) 0.17296(10) 0.0622(6) Uani 1 1 d . . . . .
O6 O 0.4431(3) 0.26434(19) 0.16280(10) 0.0643(6) Uani 1 1 d . . . . .
O14 O 1.1023(3) 0.5554(3) 0.24799(11) 0.0843(9) Uani 1 1 d D . . . .
H14 H 1.149(6) 0.556(4) 0.2119(12) 0.082(12) Uiso 1 1 d D . . . .
C1 C 0.4644(4) 0.4759(3) 0.16909(10) 0.0461(6) Uani 1 1 d . . . . .
C2 C 0.5547(4) 0.5827(3) 0.18563(11) 0.0509(7) Uani 1 1 d . . . . .
C3 C 0.7257(4) 0.5748(4) 0.21345(12) 0.0620(8) Uani 1 1 d . . . . .
H3 H 0.7873 0.6472 0.2254 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8046(4) 0.4619(4) 0.22348(12) 0.0647(9) Uani 1 1 d . . . . .
C5 C 0.7177(4) 0.3556(4) 0.20655(13) 0.0639(8) Uani 1 1 d . . . . .
H5 H 0.7745 0.2783 0.2129 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5452(4) 0.3632(3) 0.17999(11) 0.0528(7) Uani 1 1 d . . . . .
C7 C 0.1066(5) 0.5639(3) 0.04510(11) 0.0560(7) Uani 1 1 d . . . . .
C8 C 0.0340(7) 0.5223(4) -0.01223(16) 0.0873(12) Uani 1 1 d . . . . .
H8A H 0.1388 0.4989 -0.0363 0.105 Uiso 1 1 calc R U . . .
H8B H -0.0347 0.5894 -0.0299 0.105 Uiso 1 1 calc R U . . .
H8C H -0.0485 0.4518 -0.0072 0.105 Uiso 1 1 calc R U . . .
C9 C 0.2328(6) 0.6732(3) 0.03722(17) 0.0794(11) Uani 1 1 d . . . . .
H9A H 0.1611 0.7419 0.0220 0.095 Uiso 1 1 calc R U . . .
H9B H 0.3327 0.6520 0.0110 0.095 Uiso 1 1 calc R U . . .
H9C H 0.2864 0.6966 0.0736 0.095 Uiso 1 1 calc R U . . .
C10 C -0.0583(5) 0.6009(3) 0.08222(14) 0.0682(9) Uani 1 1 d . . . . .
H10A H -0.1258 0.6684 0.0643 0.082 Uiso 1 1 calc R U . . .
H10B H -0.0128 0.6272 0.1192 0.082 Uiso 1 1 calc R U . . .
H10C H -0.1416 0.5306 0.0869 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0817(7) 0.2991(3) 0.08766(18) 0.0879(13) Uani 1 1 d . . . . .
H11A H -0.0167 0.3181 0.1147 0.105 Uiso 1 1 calc R U . . .
H11B H 0.1540 0.2290 0.1012 0.105 Uiso 1 1 calc R U . . .
H11C H 0.0262 0.2790 0.0512 0.105 Uiso 1 1 calc R U . . .
C12 C 0.4521(7) 0.3999(4) 0.04038(15) 0.0845(12) Uani 1 1 d . . . . .
H12A H 0.5093 0.3255 0.0556 0.101 Uiso 1 1 calc R U . . .
H12B H 0.5387 0.4687 0.0442 0.101 Uiso 1 1 calc R U . . .
H12C H 0.4225 0.3875 0.0005 0.101 Uiso 1 1 calc R U . . .
C13 C 0.5688(6) 0.7999(3) 0.17502(16) 0.0710(10) Uani 1 1 d . . . . .
H13A H 0.6802 0.7915 0.1517 0.085 Uiso 1 1 calc R U . . .
H13B H 0.6052 0.8168 0.2140 0.085 Uiso 1 1 calc R U . . .
H13C H 0.4928 0.8676 0.1608 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9879(5) 0.4511(5) 0.25613(16) 0.0868(13) Uani 1 1 d . . . . .
H14A H 1.0561 0.3821 0.2377 0.104 Uiso 0.669(11) 1 calc R U P A 1
H14B H 1.0511 0.3696 0.2550 0.104 Uiso 0.331(11) 1 calc R U P A 2
C17 C 0.5337(6) 0.1481(3) 0.16073(16) 0.0731(9) Uani 1 1 d . . . . .
H17A H 0.5745 0.1251 0.1986 0.088 Uiso 1 1 calc R U . . .
H17B H 0.6417 0.1532 0.1358 0.088 Uiso 1 1 calc R U . . .
H17C H 0.4472 0.0863 0.1464 0.088 Uiso 1 1 calc R U . . .
C15 C 0.9449(7) 0.4060(5) 0.3148(2) 0.0618(18) Uani 0.669(11) 1 d D U P A 1
H15 H 0.8862 0.3289 0.3200 0.074 Uiso 0.669(11) 1 calc R U P A 1
C16 C 0.9885(14) 0.4729(9) 0.3586(4) 0.073(2) Uani 0.669(11) 1 d D U P A 1
H16A H 1.0473 0.5500 0.3535 0.087 Uiso 0.669(11) 1 calc R U P A 1
H16B H 0.9614 0.4444 0.3955 0.087 Uiso 0.669(11) 1 calc R U P A 1
C15A C 0.9489(13) 0.5094(10) 0.3192(4) 0.057(3) Uani 0.331(11) 1 d D U P A 2
H15A H 0.9347 0.5948 0.3256 0.068 Uiso 0.331(11) 1 calc R U P A 2
C16A C 0.939(4) 0.428(2) 0.3595(11) 0.100(8) Uani 0.331(11) 1 d D U P A 2
H16C H 0.9543 0.3438 0.3511 0.120 Uiso 0.331(11) 1 calc R U P A 2
H16D H 0.9172 0.4538 0.3971 0.120 Uiso 0.331(11) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Si1 O1 1.6696(19) . ?
Si1 C12 1.850(4) . ?
Si1 C11 1.858(4) . ?
Si1 C7 1.888(3) . ?
O1 C1 1.377(3) . ?
O2 C2 1.364(4) . ?
O2 C13 1.427(4) . ?
O6 C6 1.368(4) . ?
O6 C17 1.428(4) . ?
O14 C14 1.419(6) . ?
O14 H14 0.92(2) . ?
C1 C6 1.386(4) . ?
C1 C2 1.392(4) . ?
C2 C3 1.401(4) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C4 C14 1.536(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C7 C9 1.513(5) . ?
C7 C8 1.528(5) . ?
C7 C10 1.534(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.511(7) . ?
C14 C15A 1.652(11) . ?
C14 H14A 1.0000 . ?
C14 H14B 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 C16 1.310(11) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C15A C16A 1.306(19) . ?
C15A H15A 0.9500 . ?
C16A H16C 0.9500 . ?
C16A H16D 0.9500 . ?

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
O1 Si1 C12 108.87(15) . . ?
O1 Si1 C11 108.46(15) . . ?
C12 Si1 C11 113.3(2) . . ?
O1 Si1 C7 105.60(11) . . ?
C12 Si1 C7 110.32(16) . . ?
C11 Si1 C7 109.98(17) . . ?
C1 O1 Si1 126.37(17) . . ?
C2 O2 C13 117.5(3) . . ?
C6 O6 C17 117.7(3) . . ?
C14 O14 H14 110(3) . . ?
O1 C1 C6 121.4(3) . . ?
O1 C1 C2 118.9(3) . . ?
C6 C1 C2 119.7(3) . . ?
O2 C2 C1 115.3(2) . . ?
O2 C2 C3 125.2(3) . . ?
C1 C2 C3 119.5(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 C14 120.7(4) . . ?
C5 C4 C14 118.2(4) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
O6 C6 C1 114.8(3) . . ?
O6 C6 C5 124.5(3) . . ?
C1 C6 C5 120.7(3) . . ?
C9 C7 C8 109.3(3) . . ?
C9 C7 C10 109.2(3) . . ?
C8 C7 C10 109.0(3) . . ?
C9 C7 Si1 110.4(2) . . ?
C8 C7 Si1 109.6(2) . . ?
C10 C7 Si1 109.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 C14 C15 120.4(4) . . ?
O14 C14 C4 111.6(3) . . ?
C15 C14 C4 108.4(3) . . ?
O14 C14 C15A 85.0(4) . . ?
C4 C14 C15A 106.4(4) . . ?
O14 C14 H14A 105.0 . . ?
C15 C14 H14A 105.0 . . ?
C4 C14 H14A 105.0 . . ?
O14 C14 H14B 116.5 . . ?
C4 C14 H14B 116.5 . . ?
C15A C14 H14B 116.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C15 C14 120.2(7) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C16A C15A C14 114.4(17) . . ?
C16A C15A H15A 122.8 . . ?
C14 C15A H15A 122.8 . . ?
C15A C16A H16C 120.0 . . ?
C15A C16A H16D 120.0 . . ?
H16C C16A H16D 120.0 . . ?

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
C12 Si1 O1 C1 -14.5(3) . . . . ?
C11 Si1 O1 C1 109.2(3) . . . . ?
C7 Si1 O1 C1 -133.0(2) . . . . ?
Si1 O1 C1 C6 -61.2(3) . . . . ?
Si1 O1 C1 C2 120.9(2) . . . . ?
C13 O2 C2 C1 -163.8(3) . . . . ?
C13 O2 C2 C3 16.5(4) . . . . ?
O1 C1 C2 O2 -2.2(4) . . . . ?
C6 C1 C2 O2 179.9(3) . . . . ?
O1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
O2 C2 C3 C4 -179.4(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 C14 -177.4(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C14 C4 C5 C6 176.0(3) . . . . ?
C17 O6 C6 C1 166.0(3) . . . . ?
C17 O6 C6 C5 -14.0(4) . . . . ?
O1 C1 C6 O6 1.1(4) . . . . ?
C2 C1 C6 O6 178.9(3) . . . . ?
O1 C1 C6 C5 -178.9(2) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C4 C5 C6 O6 -178.0(3) . . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
O1 Si1 C7 C9 64.5(2) . . . . ?
C12 Si1 C7 C9 -53.0(3) . . . . ?
C11 Si1 C7 C9 -178.7(2) . . . . ?
O1 Si1 C7 C8 -175.1(3) . . . . ?
C12 Si1 C7 C8 67.4(3) . . . . ?
C11 Si1 C7 C8 -58.3(3) . . . . ?
O1 Si1 C7 C10 -55.7(2) . . . . ?
C12 Si1 C7 C10 -173.2(2) . . . . ?
C11 Si1 C7 C10 61.1(3) . . . . ?
C3 C4 C14 O14 -30.3(4) . . . . ?
C5 C4 C14 O14 152.3(3) . . . . ?
C3 C4 C14 C15 104.6(5) . . . . ?
C5 C4 C14 C15 -72.8(5) . . . . ?
C3 C4 C14 C15A 60.8(6) . . . . ?
C5 C4 C14 C15A -116.6(5) . . . . ?
O14 C14 C15 C16 10.5(8) . . . . ?
C4 C14 C15 C16 -119.7(7) . . . . ?
O14 C14 C15A C16A -141.6(14) . . . . ?
C4 C14 C15A C16A 107.3(14) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O14 H14 O1 . . 1_655 2.935(3) 0.92(3) 2.08(3) 155(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/chloroform'
####################################################################### 
# 
# 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_anti-2R_3R-3
_database_code_depnum_ccdc_archive 'CCDC 1510492'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_audit_creation_date             2016-10-13
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C13 H16 O5'
_chemical_formula_moiety         'C13 H16 O5'
_chemical_formula_weight         252.27
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.9553(2)
_cell_length_b                   8.63515(11)
_cell_length_c                   19.7885(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.8690(19)
_cell_angle_gamma                90.0000
_cell_volume                     2371.61(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18098
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      75.28
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072.00
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            27081
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_theta_max         75.624
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9303
_reflns_number_gt                8932
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.913
_reflns_Friedel_fraction_full    0.961

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1279
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         9303
_refine_ls_number_parameters     665
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0850P)²+0.9008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26418(18) 0.4895(3) -0.24861(13) 0.0388(6) Uani 1 1 d . . . . .
O2 O 0.40164(17) 0.5866(3) -0.24815(13) 0.0343(5) Uani 1 1 d . . . . .
O9 O 0.33912(16) 0.4028(3) 0.10510(12) 0.0305(5) Uani 1 1 d . . . . .
O10 O 0.19235(16) 0.5507(3) 0.11996(12) 0.0299(5) Uani 1 1 d D . . . .
O11 O 0.07025(15) 0.7212(3) 0.01310(12) 0.0295(5) Uani 1 1 d . . . . .
O21 O 0.45757(16) 0.5692(3) 0.25795(12) 0.0335(5) Uani 1 1 d . . . . .
O22 O 0.33352(16) 0.4246(3) 0.25534(13) 0.0386(6) Uani 1 1 d . . . . .
O29 O 0.75430(15) 0.5762(3) 0.59713(12) 0.0294(5) Uani 1 1 d . . . . .
O30 O 0.91164(15) 0.4170(3) 0.60547(12) 0.0308(5) Uani 1 1 d D . . . .
O31 O 0.92416(15) 0.2712(3) 0.49135(12) 0.0320(5) Uani 1 1 d . . . . .
O41 O 0.74612(15) 0.3657(3) 0.73763(12) 0.0317(5) Uani 1 1 d . . . . .
O42 O 0.89683(16) 0.3962(3) 0.74565(13) 0.0370(6) Uani 1 1 d . . . . .
O49 O 0.83114(15) 0.6657(3) 1.09881(12) 0.0283(5) Uani 1 1 d . . . . .
O50 O 0.68631(15) 0.5038(3) 1.10917(11) 0.0285(5) Uani 1 1 d D . . . .
O51 O 0.56504(16) 0.3462(3) 0.99727(12) 0.0299(5) Uani 1 1 d . . . . .
O61 O 0.97177(16) 0.4888(3) 1.22777(13) 0.0379(6) Uani 1 1 d . . . . .
O62 O 0.83641(18) 0.5482(4) 1.24466(13) 0.0452(7) Uani 1 1 d . . . . .
O69 O 1.25556(16) 0.3575(3) 1.60741(12) 0.0322(5) Uani 1 1 d . . . . .
O70 O 1.40563(15) 0.5251(3) 1.60634(12) 0.0320(5) Uani 1 1 d D . . . .
O71 O 1.40926(16) 0.6522(3) 1.48577(12) 0.0329(5) Uani 1 1 d . . . . .
C2 C 0.3455(2) 0.5719(4) -0.21777(17) 0.0282(6) Uani 1 1 d . . . . .
C3 C 0.3533(2) 0.6314(4) -0.14450(18) 0.0320(7) Uani 1 1 d . . . . .
H3A H 0.3750 0.7406 -0.1378 0.038 Uiso 1 1 calc R U . . .
H3B H 0.3989 0.5681 -0.1049 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2513(2) 0.6168(4) -0.14586(17) 0.0273(6) Uani 1 1 d . . . . .
H4 H 0.2158 0.7130 -0.1688 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2102(2) 0.4840(5) -0.19970(18) 0.0344(7) Uani 1 1 d . . . . .
H5 H 0.2223 0.3830 -0.1730 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1057(3) 0.4983(6) -0.2463(2) 0.0464(9) Uani 1 1 d . . . . .
H6A H 0.0674 0.4952 -0.2156 0.056 Uiso 1 1 calc R U . . .
H6B H 0.0945 0.5968 -0.2728 0.056 Uiso 1 1 calc R U . . .
H6C H 0.0868 0.4124 -0.2812 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2379(2) 0.5941(4) -0.07460(16) 0.0257(6) Uani 1 1 d . . . . .
C8 C 0.2983(2) 0.5005(4) -0.01958(17) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.3499 0.4468 -0.0262 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2832(2) 0.4855(4) 0.04548(16) 0.0257(6) Uani 1 1 d . . . . .
C10 C 0.2066(2) 0.5611(4) 0.05553(16) 0.0247(6) Uani 1 1 d . . . . .
C11 C 0.1449(2) 0.6518(4) -0.00042(17) 0.0256(6) Uani 1 1 d . . . . .
C12 C 0.1603(2) 0.6685(4) -0.06530(17) 0.0257(6) Uani 1 1 d . . . . .
H12 H 0.1179 0.7308 -0.1033 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4193(2) 0.3201(4) 0.10109(18) 0.0301(6) Uani 1 1 d . . . . .
H13A H 0.4528 0.2663 0.1473 0.036 Uiso 1 1 calc R U . . .
H13B H 0.3968 0.2441 0.0615 0.036 Uiso 1 1 calc R U . . .
H13C H 0.4637 0.3927 0.0917 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0113(2) 0.8245(4) -0.04086(18) 0.0304(7) Uani 1 1 d . . . . .
H14A H -0.0390 0.8666 -0.0255 0.037 Uiso 1 1 calc R U . . .
H14B H 0.0508 0.9095 -0.0473 0.037 Uiso 1 1 calc R U . . .
H14C H -0.0187 0.7690 -0.0870 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4188(2) 0.4521(4) 0.28259(17) 0.0307(7) Uani 1 1 d . . . . .
C23 C 0.4945(2) 0.3727(4) 0.34546(18) 0.0325(7) Uani 1 1 d . . . . .
H23A H 0.4867 0.2588 0.3416 0.039 Uiso 1 1 calc R U . . .
H23B H 0.4919 0.4072 0.3924 0.039 Uiso 1 1 calc R U . . .
C24 C 0.5890(2) 0.4230(4) 0.33837(17) 0.0293(6) Uani 1 1 d . . . . .
H24 H 0.6029 0.3494 0.3045 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5625(2) 0.5798(4) 0.30006(17) 0.0315(7) Uani 1 1 d . . . . .
H25 H 0.5757 0.6640 0.3372 0.038 Uiso 1 1 calc R U . . .
C26 C 0.6105(3) 0.6171(6) 0.2479(2) 0.0472(10) Uani 1 1 d . . . . .
H26A H 0.6803 0.6247 0.2745 0.057 Uiso 1 1 calc R U . . .
H26B H 0.5968 0.5350 0.2113 0.057 Uiso 1 1 calc R U . . .
H26C H 0.5859 0.7160 0.2239 0.057 Uiso 1 1 calc R U . . .
C27 C 0.6761(2) 0.4275(4) 0.40894(16) 0.0268(6) Uani 1 1 d . . . . .
C28 C 0.6729(2) 0.5090(4) 0.46884(17) 0.0269(6) Uani 1 1 d . . . . .
H28 H 0.6170 0.5664 0.4648 0.032 Uiso 1 1 calc R U . . .
C29 C 0.7512(2) 0.5061(4) 0.53424(16) 0.0257(6) Uani 1 1 d . . . . .
C30 C 0.8347(2) 0.4231(4) 0.54085(16) 0.0252(6) Uani 1 1 d . . . . .
C31 C 0.8390(2) 0.3470(4) 0.48010(17) 0.0264(6) Uani 1 1 d . . . . .
C32 C 0.7596(2) 0.3479(4) 0.41436(17) 0.0270(6) Uani 1 1 d . . . . .
H32 H 0.7625 0.2942 0.3733 0.032 Uiso 1 1 calc R U . . .
C33 C 0.9269(3) 0.1758(4) 0.43315(19) 0.0342(7) Uani 1 1 d . . . . .
H33A H 0.9906 0.1279 0.4471 0.041 Uiso 1 1 calc R U . . .
H33B H 0.8776 0.0949 0.4229 0.041 Uiso 1 1 calc R U . . .
H33C H 0.9142 0.2394 0.3895 0.041 Uiso 1 1 calc R U . . .
C34 C 0.6719(2) 0.6655(4) 0.59296(19) 0.0313(7) Uani 1 1 d . . . . .
H34A H 0.6822 0.7099 0.6409 0.038 Uiso 1 1 calc R U . . .
H34B H 0.6622 0.7492 0.5575 0.038 Uiso 1 1 calc R U . . .
H34C H 0.6148 0.5987 0.5777 0.038 Uiso 1 1 calc R U . . .
C42 C 0.8377(2) 0.4068(4) 0.77365(17) 0.0275(6) Uani 1 1 d . . . . .
C43 C 0.8505(2) 0.4587(4) 0.84820(17) 0.0301(7) Uani 1 1 d . . . . .
H43A H 0.8933 0.5502 0.8625 0.036 Uiso 1 1 calc R U . . .
H43B H 0.8782 0.3749 0.8841 0.036 Uiso 1 1 calc R U . . .
C44 C 0.7503(2) 0.4990(5) 0.84333(19) 0.0382(8) Uani 1 1 d . . . . .
H44 H 0.7361 0.6064 0.8232 0.046 Uiso 1 1 calc R U . . .
C45 C 0.6896(2) 0.3878(4) 0.78370(16) 0.0277(6) Uani 1 1 d . . . . .
H45 H 0.6809 0.2870 0.8054 0.033 Uiso 1 1 calc R U . . .
C46 C 0.5939(3) 0.4536(6) 0.7367(2) 0.0444(9) Uani 1 1 d . . . . .
H46A H 0.5544 0.4697 0.7660 0.053 Uiso 1 1 calc R U . . .
H46B H 0.6036 0.5528 0.7163 0.053 Uiso 1 1 calc R U . . .
H46C H 0.5611 0.3813 0.6970 0.053 Uiso 1 1 calc R U . . .
C47 C 0.7324(2) 0.4960(4) 0.91411(17) 0.0287(6) Uani 1 1 d . . . . .
C48 C 0.7925(2) 0.5839(4) 0.97217(17) 0.0281(6) Uani 1 1 d . . . . .
H48 H 0.8439 0.6416 0.9674 0.034 Uiso 1 1 calc R U . . .
C49 C 0.7769(2) 0.5871(4) 1.03745(16) 0.0243(6) Uani 1 1 d . . . . .
C50 C 0.7008(2) 0.5037(4) 1.04524(16) 0.0242(6) Uani 1 1 d . . . . .
C51 C 0.6399(2) 0.4193(3) 0.98625(16) 0.0250(6) Uani 1 1 d . . . . .
C52 C 0.6559(2) 0.4149(4) 0.92099(17) 0.0275(6) Uani 1 1 d . . . . .
H52 H 0.6142 0.3561 0.8811 0.033 Uiso 1 1 calc R U . . .
C53 C 0.9154(2) 0.7444(4) 1.09864(18) 0.0290(6) Uani 1 1 d . . . . .
H53A H 0.9476 0.7959 1.1456 0.035 Uiso 1 1 calc R U . . .
H53B H 0.9596 0.6693 1.0905 0.035 Uiso 1 1 calc R U . . .
H53C H 0.8968 0.8218 1.0596 0.035 Uiso 1 1 calc R U . . .
C54 C 0.5048(2) 0.2495(4) 0.94030(18) 0.0315(7) Uani 1 1 d . . . . .
H54A H 0.4544 0.2043 0.9546 0.038 Uiso 1 1 calc R U . . .
H54B H 0.4750 0.3111 0.8959 0.038 Uiso 1 1 calc R U . . .
H54C H 0.5435 0.1665 0.9311 0.038 Uiso 1 1 calc R U . . .
C60 C 1.4075(2) 0.7402(4) 1.42458(18) 0.0329(7) Uani 1 1 d . . . . .
H60A H 1.4700 0.7912 1.4358 0.040 Uiso 1 1 calc R U . . .
H60B H 1.3947 0.6715 1.3826 0.040 Uiso 1 1 calc R U . . .
H60C H 1.3567 0.8188 1.4131 0.040 Uiso 1 1 calc R U . . .
C62 C 0.9226(2) 0.5286(4) 1.26984(18) 0.0343(7) Uani 1 1 d . . . . .
C63 C 0.9903(2) 0.5427(4) 1.34719(18) 0.0346(7) Uani 1 1 d . . . . .
H63A H 0.9614 0.5006 1.3810 0.042 Uiso 1 1 calc R U . . .
H63B H 1.0091 0.6519 1.3602 0.042 Uiso 1 1 calc R U . . .
C64 C 1.0755(2) 0.4466(5) 1.34858(18) 0.0375(8) Uani 1 1 d . . . . .
H64 H 1.0567 0.3358 1.3500 0.045 Uiso 1 1 calc R U . . .
C65 C 1.0753(2) 0.4747(5) 1.27289(18) 0.0356(7) Uani 1 1 d . . . . .
H65 H 1.1094 0.5737 1.2718 0.043 Uiso 1 1 calc R U . . .
C66 C 1.1166(3) 0.3445(6) 1.2438(2) 0.0447(9) Uani 1 1 d . . . . .
H66A H 1.1854 0.3339 1.2733 0.054 Uiso 1 1 calc R U . . .
H66B H 1.0832 0.2480 1.2459 0.054 Uiso 1 1 calc R U . . .
H66C H 1.1082 0.3664 1.1932 0.054 Uiso 1 1 calc R U . . .
C67 C 1.1676(2) 0.4707(4) 1.41414(16) 0.0313(7) Uani 1 1 d . . . . .
C68 C 1.1693(2) 0.3996(4) 1.47745(18) 0.0319(7) Uani 1 1 d . . . . .
H68 H 1.1160 0.3389 1.4768 0.038 Uiso 1 1 calc R U . . .
C69 C 1.2486(2) 0.4171(4) 1.54157(17) 0.0278(6) Uani 1 1 d . . . . .
C70 C 1.3271(2) 0.5052(4) 1.54321(17) 0.0264(6) Uani 1 1 d . . . . .
C71 C 1.3266(2) 0.5731(4) 1.47885(17) 0.0274(6) Uani 1 1 d . . . . .
C72 C 1.2461(2) 0.5582(4) 1.41442(17) 0.0299(6) Uani 1 1 d . . . . .
H72 H 1.2448 0.6073 1.3711 0.036 Uiso 1 1 calc R U . . .
C73 C 1.1766(2) 0.2659(4) 1.60847(19) 0.0336(7) Uani 1 1 d . . . . .
H73A H 1.1897 0.2299 1.6582 0.040 Uiso 1 1 calc R U . . .
H73B H 1.1177 0.3286 1.5918 0.040 Uiso 1 1 calc R U . . .
H73C H 1.1681 0.1765 1.5762 0.040 Uiso 1 1 calc R U . . .
H70 H 1.386(4) 0.497(7) 1.6466(19) 0.064(15) Uiso 1 1 d D . . . .
H50 H 0.743(2) 0.548(6) 1.147(2) 0.067(16) Uiso 1 1 d D . . . .
H30 H 0.895(4) 0.433(8) 0.648(2) 0.09(2) Uiso 1 1 d D . . . .
H10 H 0.242(3) 0.483(6) 0.153(3) 0.082(19) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.344(4) . ?
O1 C5 1.474(4) . ?
O2 C2 1.208(4) . ?
O9 C9 1.366(4) . ?
O9 C13 1.424(4) . ?
O10 C10 1.372(4) . ?
O10 H10 0.978(7) . ?
O11 C11 1.379(4) . ?
O11 C14 1.419(4) . ?
O21 C22 1.344(4) . ?
O21 C25 1.481(4) . ?
O22 C22 1.209(4) . ?
O29 C29 1.369(4) . ?
O29 C34 1.429(4) . ?
O30 C30 1.366(4) . ?
O30 H30 0.978(7) . ?
O31 C31 1.374(4) . ?
O31 C33 1.428(4) . ?
O41 C42 1.334(4) . ?
O41 C45 1.469(3) . ?
O42 C42 1.210(4) . ?
O49 C49 1.363(4) . ?
O49 C53 1.433(4) . ?
O50 C50 1.361(3) . ?
O50 H50 0.979(7) . ?
O51 C51 1.371(4) . ?
O51 C54 1.423(4) . ?
O61 C62 1.345(4) . ?
O61 C65 1.476(4) . ?
O62 C62 1.208(4) . ?
O69 C69 1.368(4) . ?
O69 C73 1.428(4) . ?
O70 C70 1.369(4) . ?
O70 H70 0.976(7) . ?
O71 C71 1.375(4) . ?
O71 C60 1.422(4) . ?
C2 C3 1.501(4) . ?
C3 C4 1.520(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.510(4) . ?
C4 C5 1.530(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.496(5) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.386(4) . ?
C7 C12 1.397(4) . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(4) . ?
C10 C11 1.389(4) . ?
C11 C12 1.394(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C22 C23 1.500(5) . ?
C23 C24 1.533(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C27 1.515(4) . ?
C24 C25 1.530(5) . ?
C24 H24 1.0000 . ?
C25 C26 1.495(5) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.394(4) . ?
C27 C32 1.394(4) . ?
C28 C29 1.385(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.403(4) . ?
C30 C31 1.392(4) . ?
C31 C32 1.397(4) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C42 C43 1.485(4) . ?
C43 C44 1.506(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C47 1.521(4) . ?
C44 C45 1.530(5) . ?
C44 H44 1.0000 . ?
C45 C46 1.498(5) . ?
C45 H45 1.0000 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.391(5) . ?
C47 C52 1.391(4) . ?
C48 C49 1.395(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.404(4) . ?
C50 C51 1.390(4) . ?
C51 C52 1.399(4) . ?
C52 H52 0.9500 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C62 C63 1.493(5) . ?
C63 C64 1.512(5) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C67 1.515(4) . ?
C64 C65 1.516(5) . ?
C64 H64 1.0000 . ?
C65 C66 1.497(6) . ?
C65 H65 1.0000 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67 C68 1.387(5) . ?
C67 C72 1.394(5) . ?
C68 C69 1.385(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.390(5) . ?
C70 C71 1.399(4) . ?
C71 C72 1.395(4) . ?
C72 H72 0.9500 . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 110.0(2) . . ?
C9 O9 C13 118.2(2) . . ?
C10 O10 H10 109(3) . . ?
C11 O11 C14 116.7(2) . . ?
C22 O21 C25 110.6(2) . . ?
C29 O29 C34 116.7(2) . . ?
C30 O30 H30 114(4) . . ?
C31 O31 C33 116.5(2) . . ?
C42 O41 C45 110.3(2) . . ?
C49 O49 C53 117.8(2) . . ?
C50 O50 H50 108(3) . . ?
C51 O51 C54 117.2(2) . . ?
C62 O61 C65 109.8(3) . . ?
C69 O69 C73 116.9(3) . . ?
C70 O70 H70 107(3) . . ?
C71 O71 C60 116.8(3) . . ?
O2 C2 O1 120.6(3) . . ?
O2 C2 C3 128.8(3) . . ?
O1 C2 C3 110.6(3) . . ?
C2 C3 C4 103.8(3) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C7 C4 C3 118.4(3) . . ?
C7 C4 C5 113.2(3) . . ?
C3 C4 C5 102.4(3) . . ?
C7 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
C5 C4 H4 107.4 . . ?
O1 C5 C6 107.1(3) . . ?
O1 C5 C4 104.9(3) . . ?
C6 C5 C4 115.1(3) . . ?
O1 C5 H5 109.8 . . ?
C6 C5 H5 109.8 . . ?
C4 C5 H5 109.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.7(3) . . ?
C8 C7 C4 122.3(3) . . ?
C12 C7 C4 118.0(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O9 C9 C8 126.0(3) . . ?
O9 C9 C10 113.1(3) . . ?
C8 C9 C10 120.8(3) . . ?
O10 C10 C11 119.4(3) . . ?
O10 C10 C9 121.5(3) . . ?
C11 C10 C9 119.1(3) . . ?
O11 C11 C10 115.9(3) . . ?
O11 C11 C12 123.9(3) . . ?
C10 C11 C12 120.3(3) . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
O9 C13 H13A 109.5 . . ?
O9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O22 C22 O21 120.8(3) . . ?
O22 C22 C23 128.7(3) . . ?
O21 C22 C23 110.5(3) . . ?
C22 C23 C24 103.3(3) . . ?
C22 C23 H23A 111.1 . . ?
C24 C23 H23A 111.1 . . ?
C22 C23 H23B 111.1 . . ?
C24 C23 H23B 111.1 . . ?
H23A C23 H23B 109.1 . . ?
C27 C24 C23 115.4(3) . . ?
C27 C24 C25 114.1(3) . . ?
C23 C24 C25 102.7(3) . . ?
C27 C24 H24 108.1 . . ?
C23 C24 H24 108.1 . . ?
C25 C24 H24 108.1 . . ?
O21 C25 C26 107.8(3) . . ?
O21 C25 C24 104.4(3) . . ?
C26 C25 C24 115.5(3) . . ?
O21 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C24 C25 H25 109.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 119.8(3) . . ?
C28 C27 C24 120.4(3) . . ?
C32 C27 C24 119.8(3) . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
O29 C29 C28 124.9(3) . . ?
O29 C29 C30 114.4(3) . . ?
C28 C29 C30 120.6(3) . . ?
O30 C30 C31 119.7(3) . . ?
O30 C30 C29 121.1(3) . . ?
C31 C30 C29 119.1(3) . . ?
O31 C31 C30 115.0(3) . . ?
O31 C31 C32 124.6(3) . . ?
C30 C31 C32 120.3(3) . . ?
C27 C32 C31 120.0(3) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
O31 C33 H33A 109.5 . . ?
O31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O29 C34 H34A 109.5 . . ?
O29 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O29 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O42 C42 O41 121.0(3) . . ?
O42 C42 C43 129.2(3) . . ?
O41 C42 C43 109.8(2) . . ?
C42 C43 C44 104.4(3) . . ?
C42 C43 H43A 110.9 . . ?
C44 C43 H43A 110.9 . . ?
C42 C43 H43B 110.9 . . ?
C44 C43 H43B 110.9 . . ?
H43A C43 H43B 108.9 . . ?
C43 C44 C47 116.7(3) . . ?
C43 C44 C45 101.2(3) . . ?
C47 C44 C45 116.2(3) . . ?
C43 C44 H44 107.4 . . ?
C47 C44 H44 107.4 . . ?
C45 C44 H44 107.4 . . ?
O41 C45 C46 107.5(2) . . ?
O41 C45 C44 104.3(2) . . ?
C46 C45 C44 113.3(3) . . ?
O41 C45 H45 110.5 . . ?
C46 C45 H45 110.5 . . ?
C44 C45 H45 110.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C52 119.7(3) . . ?
C48 C47 C44 118.1(3) . . ?
C52 C47 C44 122.1(3) . . ?
C47 C48 C49 119.8(3) . . ?
C47 C48 H48 120.1 . . ?
C49 C48 H48 120.1 . . ?
O49 C49 C48 125.8(3) . . ?
O49 C49 C50 113.3(2) . . ?
C48 C49 C50 120.9(3) . . ?
O50 C50 C51 120.0(3) . . ?
O50 C50 C49 121.2(3) . . ?
C51 C50 C49 118.8(3) . . ?
O51 C51 C50 115.2(3) . . ?
O51 C51 C52 124.4(3) . . ?
C50 C51 C52 120.4(3) . . ?
C47 C52 C51 120.4(3) . . ?
C47 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
O49 C53 H53A 109.5 . . ?
O49 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O49 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O51 C54 H54A 109.5 . . ?
O51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O71 C60 H60A 109.5 . . ?
O71 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
O71 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
O62 C62 O61 121.7(3) . . ?
O62 C62 C63 128.6(3) . . ?
O61 C62 C63 109.7(3) . . ?
C62 C63 C64 102.7(3) . . ?
C62 C63 H63A 111.2 . . ?
C64 C63 H63A 111.2 . . ?
C62 C63 H63B 111.2 . . ?
C64 C63 H63B 111.2 . . ?
H63A C63 H63B 109.1 . . ?
C63 C64 C67 115.6(3) . . ?
C63 C64 C65 101.7(3) . . ?
C67 C64 C65 119.4(3) . . ?
C63 C64 H64 106.4 . . ?
C67 C64 H64 106.4 . . ?
C65 C64 H64 106.4 . . ?
O61 C65 C66 108.6(3) . . ?
O61 C65 C64 103.1(2) . . ?
C66 C65 C64 114.2(3) . . ?
O61 C65 H65 110.2 . . ?
C66 C65 H65 110.2 . . ?
C64 C65 H65 110.2 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C68 C67 C72 120.3(3) . . ?
C68 C67 C64 114.6(3) . . ?
C72 C67 C64 125.0(3) . . ?
C67 C68 C69 120.0(3) . . ?
C67 C68 H68 120.0 . . ?
C69 C68 H68 120.0 . . ?
O69 C69 C68 124.5(3) . . ?
O69 C69 C70 114.8(3) . . ?
C68 C69 C70 120.6(3) . . ?
O70 C70 C69 121.3(3) . . ?
O70 C70 C71 119.4(3) . . ?
C69 C70 C71 119.3(3) . . ?
O71 C71 C72 125.1(3) . . ?
O71 C71 C70 114.7(3) . . ?
C72 C71 C70 120.3(3) . . ?
C67 C72 C71 119.4(3) . . ?
C67 C72 H72 120.3 . . ?
C71 C72 H72 120.3 . . ?
O69 C73 H73A 109.5 . . ?
O69 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
O69 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?

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
C5 O1 C2 O2 177.8(3) . . . . ?
C5 O1 C2 C3 -0.5(4) . . . . ?
O2 C2 C3 C4 164.5(3) . . . . ?
O1 C2 C3 C4 -17.4(4) . . . . ?
C2 C3 C4 C7 152.1(3) . . . . ?
C2 C3 C4 C5 26.8(3) . . . . ?
C2 O1 C5 C6 140.9(3) . . . . ?
C2 O1 C5 C4 18.1(4) . . . . ?
C7 C4 C5 O1 -156.2(3) . . . . ?
C3 C4 C5 O1 -27.5(3) . . . . ?
C7 C4 C5 C6 86.4(4) . . . . ?
C3 C4 C5 C6 -144.9(3) . . . . ?
C3 C4 C7 C8 -39.2(4) . . . . ?
C5 C4 C7 C8 80.7(4) . . . . ?
C3 C4 C7 C12 142.1(3) . . . . ?
C5 C4 C7 C12 -98.0(3) . . . . ?
C12 C7 C8 C9 -2.1(5) . . . . ?
C4 C7 C8 C9 179.1(3) . . . . ?
C13 O9 C9 C8 -1.7(4) . . . . ?
C13 O9 C9 C10 179.7(3) . . . . ?
C7 C8 C9 O9 -177.2(3) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
O9 C9 C10 O10 0.4(4) . . . . ?
C8 C9 C10 O10 -178.3(3) . . . . ?
O9 C9 C10 C11 178.9(3) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C14 O11 C11 C10 174.8(3) . . . . ?
C14 O11 C11 C12 -5.1(4) . . . . ?
O10 C10 C11 O11 -2.3(4) . . . . ?
C9 C10 C11 O11 179.2(3) . . . . ?
O10 C10 C11 C12 177.6(3) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
O11 C11 C12 C7 180.0(3) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C8 C7 C12 C11 1.5(4) . . . . ?
C4 C7 C12 C11 -179.8(3) . . . . ?
C25 O21 C22 O22 179.8(3) . . . . ?
C25 O21 C22 C23 1.0(4) . . . . ?
O22 C22 C23 C24 162.7(3) . . . . ?
O21 C22 C23 C24 -18.6(4) . . . . ?
C22 C23 C24 C27 152.3(3) . . . . ?
C22 C23 C24 C25 27.5(3) . . . . ?
C22 O21 C25 C26 140.5(3) . . . . ?
C22 O21 C25 C24 17.2(3) . . . . ?
C27 C24 C25 O21 -152.9(3) . . . . ?
C23 C24 C25 O21 -27.3(3) . . . . ?
C27 C24 C25 C26 88.9(3) . . . . ?
C23 C24 C25 C26 -145.5(3) . . . . ?
C23 C24 C27 C28 -52.2(4) . . . . ?
C25 C24 C27 C28 66.3(4) . . . . ?
C23 C24 C27 C32 126.8(3) . . . . ?
C25 C24 C27 C32 -114.7(3) . . . . ?
C32 C27 C28 C29 -2.3(5) . . . . ?
C24 C27 C28 C29 176.7(3) . . . . ?
C34 O29 C29 C28 -3.5(4) . . . . ?
C34 O29 C29 C30 178.5(3) . . . . ?
C27 C28 C29 O29 -177.1(3) . . . . ?
C27 C28 C29 C30 0.7(5) . . . . ?
O29 C29 C30 O30 -0.7(4) . . . . ?
C28 C29 C30 O30 -178.7(3) . . . . ?
O29 C29 C30 C31 179.9(3) . . . . ?
C28 C29 C30 C31 1.8(4) . . . . ?
C33 O31 C31 C30 172.3(3) . . . . ?
C33 O31 C31 C32 -6.0(4) . . . . ?
O30 C30 C31 O31 -0.6(4) . . . . ?
C29 C30 C31 O31 178.9(3) . . . . ?
O30 C30 C31 C32 177.8(3) . . . . ?
C29 C30 C31 C32 -2.7(4) . . . . ?
C28 C27 C32 C31 1.4(5) . . . . ?
C24 C27 C32 C31 -177.7(3) . . . . ?
O31 C31 C32 C27 179.4(3) . . . . ?
C30 C31 C32 C27 1.2(5) . . . . ?
C45 O41 C42 O42 179.3(3) . . . . ?
C45 O41 C42 C43 0.7(4) . . . . ?
O42 C42 C43 C44 161.3(4) . . . . ?
O41 C42 C43 C44 -20.2(4) . . . . ?
C42 C43 C44 C47 157.0(3) . . . . ?
C42 C43 C44 C45 29.8(4) . . . . ?
C42 O41 C45 C46 139.4(3) . . . . ?
C42 O41 C45 C44 18.8(4) . . . . ?
C43 C44 C45 O41 -29.5(3) . . . . ?
C47 C44 C45 O41 -156.9(3) . . . . ?
C43 C44 C45 C46 -146.1(3) . . . . ?
C47 C44 C45 C46 86.4(4) . . . . ?
C43 C44 C47 C48 54.4(5) . . . . ?
C45 C44 C47 C48 173.8(3) . . . . ?
C43 C44 C47 C52 -128.8(4) . . . . ?
C45 C44 C47 C52 -9.4(5) . . . . ?
C52 C47 C48 C49 1.5(5) . . . . ?
C44 C47 C48 C49 178.4(3) . . . . ?
C53 O49 C49 C48 -4.3(4) . . . . ?
C53 O49 C49 C50 175.0(3) . . . . ?
C47 C48 C49 O49 178.7(3) . . . . ?
C47 C48 C49 C50 -0.6(5) . . . . ?
O49 C49 C50 O50 -0.7(4) . . . . ?
C48 C49 C50 O50 178.7(3) . . . . ?
O49 C49 C50 C51 179.7(3) . . . . ?
C48 C49 C50 C51 -0.9(4) . . . . ?
C54 O51 C51 C50 -175.7(3) . . . . ?
C54 O51 C51 C52 5.5(4) . . . . ?
O50 C50 C51 O51 2.9(4) . . . . ?
C49 C50 C51 O51 -177.4(3) . . . . ?
O50 C50 C51 C52 -178.2(3) . . . . ?
C49 C50 C51 C52 1.5(4) . . . . ?
C48 C47 C52 C51 -1.0(5) . . . . ?
C44 C47 C52 C51 -177.8(3) . . . . ?
O51 C51 C52 C47 178.3(3) . . . . ?
C50 C51 C52 C47 -0.5(5) . . . . ?
C65 O61 C62 O62 179.4(4) . . . . ?
C65 O61 C62 C63 -0.6(4) . . . . ?
O62 C62 C63 C64 158.5(4) . . . . ?
O61 C62 C63 C64 -21.6(4) . . . . ?
C62 C63 C64 C67 164.5(3) . . . . ?
C62 C63 C64 C65 33.7(4) . . . . ?
C62 O61 C65 C66 143.9(3) . . . . ?
C62 O61 C65 C64 22.5(4) . . . . ?
C63 C64 C65 O61 -34.3(4) . . . . ?
C67 C64 C65 O61 -162.7(3) . . . . ?
C63 C64 C65 C66 -151.9(3) . . . . ?
C67 C64 C65 C66 79.7(4) . . . . ?
C63 C64 C67 C68 76.7(4) . . . . ?
C65 C64 C67 C68 -161.6(3) . . . . ?
C63 C64 C67 C72 -102.3(4) . . . . ?
C65 C64 C67 C72 19.5(6) . . . . ?
C72 C67 C68 C69 0.9(5) . . . . ?
C64 C67 C68 C69 -178.1(3) . . . . ?
C73 O69 C69 C68 2.6(5) . . . . ?
C73 O69 C69 C70 -179.9(3) . . . . ?
C67 C68 C69 O69 177.1(3) . . . . ?
C67 C68 C69 C70 -0.3(5) . . . . ?
O69 C69 C70 O70 1.7(4) . . . . ?
C68 C69 C70 O70 179.3(3) . . . . ?
O69 C69 C70 C71 -179.2(3) . . . . ?
C68 C69 C70 C71 -1.6(5) . . . . ?
C60 O71 C71 C72 7.8(5) . . . . ?
C60 O71 C71 C70 -171.9(3) . . . . ?
O70 C70 C71 O71 1.8(4) . . . . ?
C69 C70 C71 O71 -177.4(3) . . . . ?
O70 C70 C71 C72 -178.0(3) . . . . ?
C69 C70 C71 C72 2.8(5) . . . . ?
C68 C67 C72 C71 0.3(5) . . . . ?
C64 C67 C72 C71 179.2(3) . . . . ?
O71 C71 C72 C67 178.1(3) . . . . ?
C70 C71 C72 C67 -2.2(5) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10 O9 . . . 2.649(4) 0.98(4) 2.13(6) 111(4) no
O10 H10 O22 . . . 2.934(3) 0.98(4) 2.04(4) 151(5) no
O30 H30 O29 . . . 2.677(3) 0.98(6) 2.32(6) 100(3) no
O30 H30 O42 . . . 2.869(4) 0.98(6) 1.94(5) 157(6) no
O50 H50 O49 . . . 2.649(3) 0.98(3) 2.14(5) 110(3) no
O50 H50 O62 . . . 2.809(3) 0.98(3) 1.92(3) 151(4) no
O70 H70 O2 . . 1_657 2.950(4) 0.98(5) 2.15(4) 138(4) no
O70 H70 O69 . . . 2.677(4) 0.98(5) 2.18(5) 110(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_S-minus-9b
_database_code_depnum_ccdc_archive 'CCDC 1505598'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_audit_creation_date             2016-09-09
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H24 O7'
_chemical_formula_moiety         'C18 H24 O7'
_chemical_formula_weight         352.38
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.308(7)
_cell_length_b                   6.220(3)
_cell_length_c                   13.145(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.591(11)
_cell_angle_gamma                90.0000
_cell_volume                     953.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    939
_cell_measurement_theta_min      40.00
_cell_measurement_theta_max      67.90
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376.00
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_T_max  0.954

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            9483
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_theta_max         67.939
_diffrn_reflns_theta_min         3.548
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3075
_reflns_number_gt                2897
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_max     0.750
_reflns_Friedel_fraction_full    0.754

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0869
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     232
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0580P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.98079(11) 0.6757(2) 0.76578(11) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.81141(12) 0.9494(3) 0.67605(12) 0.0373(4) Uani 1 1 d . . . . .
O6 O 0.95111(12) 0.3320(3) 0.87049(12) 0.0364(4) Uani 1 1 d . . . . .
O7 O 0.92521(13) 0.5166(3) 0.60459(12) 0.0468(4) Uani 1 1 d . . . . .
O13 O 0.50596(11) 0.3376(3) 0.79358(11) 0.0326(3) Uani 1 1 d . . . . .
O16 O 0.45034(13) 0.4528(3) 0.62172(11) 0.0418(4) Uani 1 1 d . . . . .
O17 O 0.43085(12) 0.1092(3) 0.66848(12) 0.0398(4) Uani 1 1 d . . . . .
C1 C 0.87316(15) 0.6394(3) 0.77553(15) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.78511(16) 0.7852(3) 0.73186(15) 0.0289(4) Uani 1 1 d . . . . .
C3 C 0.68029(16) 0.7547(3) 0.74912(15) 0.0285(4) Uani 1 1 d . . . . .
H3 H 0.6188 0.8517 0.7191 0.034 Uiso 1 1 calc R U . . .
C4 C 0.66627(15) 0.5817(3) 0.81039(14) 0.0280(4) Uani 1 1 d . . . . .
C5 C 0.75431(17) 0.4347(4) 0.85378(15) 0.0293(4) Uani 1 1 d . . . . .
H5 H 0.7436 0.3169 0.8956 0.035 Uiso 1 1 calc R U . . .
C6 C 0.85813(16) 0.4635(3) 0.83469(15) 0.0286(4) Uani 1 1 d . . . . .
C7 C 0.99861(16) 0.6006(4) 0.67557(16) 0.0308(4) Uani 1 1 d . . . . .
C8 C 1.12219(17) 0.6394(4) 0.67992(18) 0.0378(5) Uani 1 1 d . . . . .
C9 C 1.1395(2) 0.5503(6) 0.5784(2) 0.0564(7) Uani 1 1 d . . . . .
H9A H 1.0925 0.6318 0.5162 0.068 Uiso 1 1 calc R U . . .
H9B H 1.1167 0.3987 0.5701 0.068 Uiso 1 1 calc R U . . .
H9C H 1.2205 0.5628 0.5836 0.068 Uiso 1 1 calc R U . . .
C10 C 1.1459(2) 0.8813(5) 0.6885(3) 0.0588(8) Uani 1 1 d . . . . .
H10A H 1.0961 0.9532 0.6242 0.071 Uiso 1 1 calc R U . . .
H10B H 1.2263 0.9074 0.6947 0.071 Uiso 1 1 calc R U . . .
H10C H 1.1305 0.9381 0.7521 0.071 Uiso 1 1 calc R U . . .
C11 C 1.2005(2) 0.5211(7) 0.7784(2) 0.0628(8) Uani 1 1 d . . . . .
H11A H 1.2795 0.5239 0.7766 0.075 Uiso 1 1 calc R U . . .
H11B H 1.1751 0.3717 0.7776 0.075 Uiso 1 1 calc R U . . .
H11C H 1.1971 0.5921 0.8438 0.075 Uiso 1 1 calc R U . . .
C12 C 0.72430(17) 1.1044(4) 0.62877(16) 0.0349(5) Uani 1 1 d . . . . .
H12A H 0.6931 1.1598 0.6835 0.042 Uiso 1 1 calc R U . . .
H12B H 0.6628 1.0365 0.5711 0.042 Uiso 1 1 calc R U . . .
H12C H 0.7572 1.2232 0.5993 0.042 Uiso 1 1 calc R U . . .
C13 C 0.55272(16) 0.5522(4) 0.82948(16) 0.0321(4) Uani 1 1 d . . . . .
H13 H 0.4979 0.6629 0.7871 0.039 Uiso 1 1 calc R U . . .
C14 C 0.55550(19) 0.5644(4) 0.94474(18) 0.0419(5) Uani 1 1 d . . . . .
H14 H 0.4873 0.5253 0.9594 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6428(2) 0.6236(5) 1.0266(2) 0.0530(7) Uani 1 1 d . . . . .
H15A H 0.7128 0.6641 1.0161 0.064 Uiso 1 1 calc R U . . .
H15B H 0.6361 0.6260 1.0967 0.064 Uiso 1 1 calc R U . . .
C16 C 0.46088(15) 0.3146(4) 0.68718(16) 0.0298(4) Uani 1 1 d . . . . .
C17 C 0.3789(2) 0.0542(5) 0.55685(19) 0.0525(7) Uani 1 1 d . . . . .
H17A H 0.4270 0.1076 0.5155 0.063 Uiso 1 1 calc R U . . .
H17B H 0.3027 0.1199 0.5297 0.063 Uiso 1 1 calc R U . . .
H17C H 0.3717 -0.1024 0.5494 0.063 Uiso 1 1 calc R U . . .
C18 C 0.9428(2) 0.1515(4) 0.93432(19) 0.0440(5) Uani 1 1 d . . . . .
H18A H 0.8779 0.0615 0.8943 0.053 Uiso 1 1 calc R U . . .
H18B H 0.9310 0.2015 1.0007 0.053 Uiso 1 1 calc R U . . .
H18C H 1.0137 0.0674 0.9519 0.053 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.356(3) . ?
O1 C1 1.390(2) . ?
O2 C2 1.355(3) . ?
O2 C12 1.428(3) . ?
O6 C6 1.363(3) . ?
O6 C18 1.425(3) . ?
O7 C7 1.192(3) . ?
O13 C16 1.338(2) . ?
O13 C13 1.471(3) . ?
O16 C16 1.194(3) . ?
O17 C16 1.331(3) . ?
O17 C17 1.443(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 C13 1.508(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.523(3) . ?
C8 C9 1.521(4) . ?
C8 C10 1.530(4) . ?
C8 C11 1.533(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.507(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.308(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C1 116.70(14) . . ?
C2 O2 C12 117.93(16) . . ?
C6 O6 C18 117.77(17) . . ?
C16 O13 C13 114.96(16) . . ?
C16 O17 C17 114.99(19) . . ?
C6 C1 C2 121.35(17) . . ?
C6 C1 O1 118.76(17) . . ?
C2 C1 O1 119.78(18) . . ?
O2 C2 C1 115.22(17) . . ?
O2 C2 C3 125.77(18) . . ?
C1 C2 C3 119.00(18) . . ?
C4 C3 C2 119.58(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.48(18) . . ?
C3 C4 C13 118.97(18) . . ?
C5 C4 C13 119.54(18) . . ?
C6 C5 C4 118.75(19) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
O6 C6 C1 114.78(17) . . ?
O6 C6 C5 125.4(2) . . ?
C1 C6 C5 119.81(18) . . ?
O7 C7 O1 122.80(18) . . ?
O7 C7 C8 126.68(19) . . ?
O1 C7 C8 110.52(17) . . ?
C9 C8 C7 109.06(19) . . ?
C9 C8 C10 110.3(2) . . ?
C7 C8 C10 108.9(2) . . ?
C9 C8 C11 109.8(2) . . ?
C7 C8 C11 107.89(19) . . ?
C10 C8 C11 110.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O13 C13 C14 104.43(17) . . ?
O13 C13 C4 110.22(16) . . ?
C14 C13 C4 115.86(16) . . ?
O13 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
C4 C13 H13 108.7 . . ?
C15 C14 C13 126.2(2) . . ?
C15 C14 H14 116.9 . . ?
C13 C14 H14 116.9 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
O16 C16 O17 126.74(19) . . ?
O16 C16 O13 126.2(2) . . ?
O17 C16 O13 107.10(18) . . ?
O17 C17 H17A 109.5 . . ?
O17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C6 96.6(2) . . . . ?
C7 O1 C1 C2 -87.3(2) . . . . ?
C12 O2 C2 C1 179.75(18) . . . . ?
C12 O2 C2 C3 -1.1(3) . . . . ?
C6 C1 C2 O2 179.96(17) . . . . ?
O1 C1 C2 O2 3.9(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
O1 C1 C2 C3 -175.34(16) . . . . ?
O2 C2 C3 C4 -178.34(19) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C13 179.28(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C13 C4 C5 C6 179.53(16) . . . . ?
C18 O6 C6 C1 178.30(17) . . . . ?
C18 O6 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 O6 178.65(17) . . . . ?
O1 C1 C6 O6 -5.2(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
O1 C1 C6 C5 174.19(17) . . . . ?
C4 C5 C6 O6 -179.10(18) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C1 O1 C7 O7 3.7(3) . . . . ?
C1 O1 C7 C8 -176.28(17) . . . . ?
O7 C7 C8 C9 -0.8(3) . . . . ?
O1 C7 C8 C9 179.2(2) . . . . ?
O7 C7 C8 C10 119.5(3) . . . . ?
O1 C7 C8 C10 -60.5(2) . . . . ?
O7 C7 C8 C11 -120.1(3) . . . . ?
O1 C7 C8 C11 59.9(3) . . . . ?
C16 O13 C13 C14 159.16(16) . . . . ?
C16 O13 C13 C4 -75.8(2) . . . . ?
C3 C4 C13 O13 123.96(19) . . . . ?
C5 C4 C13 O13 -55.6(2) . . . . ?
C3 C4 C13 C14 -117.8(2) . . . . ?
C5 C4 C13 C14 62.7(3) . . . . ?
O13 C13 C14 C15 130.5(3) . . . . ?
C4 C13 C14 C15 9.0(4) . . . . ?
C17 O17 C16 O16 -1.0(3) . . . . ?
C17 O17 C16 O13 179.34(17) . . . . ?
C13 O13 C16 O16 -4.2(3) . . . . ?
C13 O13 C16 O17 175.44(15) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#====END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/chloroform'
####################################################################### 
# 
# 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_anti-plus-minus-3
_database_code_depnum_ccdc_archive 'CCDC 1505597'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_audit_creation_date             2016-09-09
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H16 O5'
_chemical_formula_moiety         'C13 H16 O5'
_chemical_formula_weight         252.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.4671(13)
_cell_length_b                   32.535(5)
_cell_length_c                   5.2751(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.583(4)
_cell_angle_gamma                90.0000
_cell_volume                     1214.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1213
_cell_measurement_theta_min      18.40
_cell_measurement_theta_max      46.70
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.00
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.956

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            16282
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_theta_max         68.077
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2191
_reflns_number_gt                2070
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1135
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2191
_refine_ls_number_parameters     171
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0637P)²+0.2309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.09311(14) 0.72762(3) 0.7853(2) 0.0393(3) Uani 1 1 d D . . . .
H1 H -0.061(3) 0.7412(6) 0.950(4) 0.071(6) Uiso 1 1 d D . . . .
O2 O -0.20495(13) 0.67513(3) 0.38830(19) 0.0406(3) Uani 1 1 d . . . . .
O7 O 0.16621(17) 0.46606(3) 0.7379(2) 0.0459(3) Uani 1 1 d . . . . .
O8 O 0.32759(14) 0.51631(3) 0.62420(19) 0.0398(3) Uani 1 1 d . . . . .
O11 O 0.20082(13) 0.71122(3) 1.22959(19) 0.0370(3) Uani 1 1 d . . . . .
C1 C 0.00130(18) 0.69102(4) 0.8123(3) 0.0308(3) Uani 1 1 d . . . . .
C2 C -0.05864(18) 0.66251(4) 0.6046(3) 0.0313(3) Uani 1 1 d . . . . .
C3 C 0.02755(18) 0.62424(4) 0.6262(3) 0.0314(3) Uani 1 1 d . . . . .
H3 H -0.0163 0.6047 0.4860 0.038 Uiso 1 1 calc R U . . .
C4 C 0.17835(17) 0.61443(4) 0.8532(2) 0.0289(3) Uani 1 1 d . . . . .
C5 C 0.27083(18) 0.57242(4) 0.8779(2) 0.0309(3) Uani 1 1 d . . . . .
H5 H 0.3820 0.5719 1.0450 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1412(2) 0.53635(4) 0.8851(3) 0.0366(3) Uani 1 1 d . . . . .
H6A H 0.1533 0.5289 1.0717 0.044 Uiso 1 1 calc R U . . .
H6B H 0.0077 0.5432 0.7887 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2080(2) 0.50189(4) 0.7482(3) 0.0357(3) Uani 1 1 d . . . . .
C8 C 0.33889(19) 0.56120(4) 0.6393(2) 0.0324(3) Uani 1 1 d . . . . .
H8 H 0.2494 0.5731 0.4719 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5366(2) 0.57425(4) 0.6636(3) 0.0384(4) Uani 1 1 d . . . . .
H9A H 0.5710 0.5633 0.5124 0.046 Uiso 1 1 calc R U . . .
H9B H 0.6243 0.5636 0.8312 0.046 Uiso 1 1 calc R U . . .
H9C H 0.5435 0.6043 0.6632 0.046 Uiso 1 1 calc R U . . .
C10 C 0.24130(17) 0.64306(4) 1.0587(2) 0.0286(3) Uani 1 1 d . . . . .
H10 H 0.3447 0.6366 1.2130 0.034 Uiso 1 1 calc R U . . .
C11 C 0.15282(18) 0.68118(4) 1.0382(3) 0.0294(3) Uani 1 1 d . . . . .
C12 C -0.2647(2) 0.64755(5) 0.1673(3) 0.0390(4) Uani 1 1 d . . . . .
H12A H -0.3153 0.6225 0.2219 0.047 Uiso 1 1 calc R U . . .
H12B H -0.1569 0.6405 0.1078 0.047 Uiso 1 1 calc R U . . .
H12C H -0.3631 0.6607 0.0203 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3569(2) 0.70374(4) 1.4651(3) 0.0392(3) Uani 1 1 d . . . . .
H13A H 0.4712 0.6992 1.4157 0.047 Uiso 1 1 calc R U . . .
H13B H 0.3311 0.6793 1.5568 0.047 Uiso 1 1 calc R U . . .
H13C H 0.3755 0.7276 1.5844 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.3678(15) . ?
O1 H1 0.937(16) . ?
O2 C2 1.3675(16) . ?
O2 C12 1.4254(17) . ?
O7 C7 1.2035(17) . ?
O8 C7 1.3486(18) . ?
O8 C8 1.4637(15) . ?
O11 C11 1.3686(15) . ?
O11 C13 1.4276(17) . ?
C1 C11 1.3939(19) . ?
C1 C2 1.3959(18) . ?
C2 C3 1.3897(18) . ?
C3 C4 1.3942(19) . ?
C3 H3 0.9500 . ?
C4 C10 1.3927(17) . ?
C4 C5 1.5181(16) . ?
C5 C6 1.5294(18) . ?
C5 C8 1.5436(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.5018(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.502(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3931(17) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110.1(14) . . ?
C2 O2 C12 116.89(10) . . ?
C7 O8 C8 110.87(10) . . ?
C11 O11 C13 118.00(10) . . ?
O1 C1 C11 122.69(11) . . ?
O1 C1 C2 118.10(12) . . ?
C11 C1 C2 119.21(11) . . ?
O2 C2 C3 124.29(12) . . ?
O2 C2 C1 115.25(11) . . ?
C3 C2 C1 120.46(12) . . ?
C2 C3 C4 120.10(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C10 C4 C3 119.69(11) . . ?
C10 C4 C5 120.26(11) . . ?
C3 C4 C5 120.04(11) . . ?
C4 C5 C6 114.77(11) . . ?
C4 C5 C8 113.69(10) . . ?
C6 C5 C8 102.37(10) . . ?
C4 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C8 C5 H5 108.6 . . ?
C7 C6 C5 104.55(11) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
O7 C7 O8 121.13(12) . . ?
O7 C7 C6 128.61(13) . . ?
O8 C7 C6 110.26(11) . . ?
O8 C8 C9 108.95(10) . . ?
O8 C8 C5 104.61(10) . . ?
C9 C8 C5 115.70(11) . . ?
O8 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C5 C8 H8 109.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 C11 120.06(12) . . ?
C4 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O11 C11 C10 124.91(12) . . ?
O11 C11 C1 114.64(11) . . ?
C10 C11 C1 120.44(11) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O11 C13 H13A 109.5 . . ?
O11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C12 O2 C2 C3 -3.18(18) . . . . ?
C12 O2 C2 C1 177.36(11) . . . . ?
O1 C1 C2 O2 1.98(17) . . . . ?
C11 C1 C2 O2 -178.43(11) . . . . ?
O1 C1 C2 C3 -177.50(11) . . . . ?
C11 C1 C2 C3 2.09(18) . . . . ?
O2 C2 C3 C4 178.84(11) . . . . ?
C1 C2 C3 C4 -1.73(19) . . . . ?
C2 C3 C4 C10 0.41(19) . . . . ?
C2 C3 C4 C5 179.26(11) . . . . ?
C10 C4 C5 C6 115.86(13) . . . . ?
C3 C4 C5 C6 -62.99(15) . . . . ?
C10 C4 C5 C8 -126.75(12) . . . . ?
C3 C4 C5 C8 54.40(16) . . . . ?
C4 C5 C6 C7 146.98(11) . . . . ?
C8 C5 C6 C7 23.33(13) . . . . ?
C8 O8 C7 O7 173.38(12) . . . . ?
C8 O8 C7 C6 -5.80(15) . . . . ?
C5 C6 C7 O7 168.92(14) . . . . ?
C5 C6 C7 O8 -11.98(14) . . . . ?
C7 O8 C8 C9 145.28(11) . . . . ?
C7 O8 C8 C5 21.00(13) . . . . ?
C4 C5 C8 O8 -151.08(10) . . . . ?
C6 C5 C8 O8 -26.71(13) . . . . ?
C4 C5 C8 C9 89.06(14) . . . . ?
C6 C5 C8 C9 -146.56(11) . . . . ?
C3 C4 C10 C11 0.52(18) . . . . ?
C5 C4 C10 C11 -178.33(11) . . . . ?
C13 O11 C11 C10 2.08(18) . . . . ?
C13 O11 C11 C1 -178.92(11) . . . . ?
C4 C10 C11 O11 178.81(11) . . . . ?
C4 C10 C11 C1 -0.14(18) . . . . ?
O1 C1 C11 O11 -0.63(17) . . . . ?
C2 C1 C11 O11 179.79(11) . . . . ?
O1 C1 C11 C10 178.42(11) . . . . ?
C2 C1 C11 C10 -1.15(18) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O1 . . 4_576 3.0129(16) 0.937(18) 2.12(2) 160(2) no
O1 H1 O11 . . . 2.7047(13) 0.937(18) 2.261(19) 108.2(16) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/ethyl acetate/acetone'
####################################################################### 
# 
# 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_26
_database_code_depnum_ccdc_archive 'CCDC 1506889'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_audit_creation_date             2016-09-26
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H44 N O7.5 S2.5 Si'
_chemical_formula_moiety         'C17 H29 N O5 Si, 2.5(C2 H6 O S)'
_chemical_formula_weight         550.83
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        I2/a
_space_group_name_Hall           '-I 2ya'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   10.1923(18)
_cell_length_b                   18.865(3)
_cell_length_c                   31.000(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.926(6)
_cell_angle_gamma                90.0000
_cell_volume                     5957.3(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2907
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376.00
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            35776
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_theta_max         25.387
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5450
_reflns_number_gt                3505
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.1069
_refine_ls_wR_factor_ref         0.3146
_refine_ls_wR_factor_gt          0.2790
_refine_ls_number_restraints     21
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5450
_refine_ls_number_parameters     333
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1395P)²+71.4406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         3.08
_refine_diff_density_min         -0.64
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Si Si 0.0817 0.0704
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S21 S 0.72879(17) 0.77327(10) 0.57941(6) 0.0392(5) Uani 1 1 d . . . . .
S31 S 0.2883(3) 0.74972(18) 0.51970(11) 0.0317(7) Uani 0.5 1 d . . P . .
S41 S 0.8132(2) 0.51643(12) 0.58198(8) 0.0545(6) Uani 1 1 d . U . . .
Si1 Si 0.5150(2) 0.68721(11) 0.70879(6) 0.0398(5) Uani 1 1 d . . . . .
O1 O 0.4247(4) 0.6918(2) 0.66330(14) 0.0306(10) Uani 1 1 d . . . . .
O2 O 0.1747(5) 0.6575(3) 0.64891(17) 0.0427(12) Uani 1 1 d . . . . .
O6 O 0.5099(4) 0.8244(2) 0.65053(17) 0.0388(12) Uani 1 1 d . . . . .
O16 O -0.1936(4) 0.9627(3) 0.58427(18) 0.0431(13) Uani 1 1 d . . . . .
O17 O -0.0690(5) 1.0260(2) 0.54142(15) 0.0377(11) Uani 1 1 d . . . . .
O21 O 0.8509(5) 0.7537(3) 0.55641(19) 0.0519(15) Uani 1 1 d . . . . .
O31 O 0.2500 0.8235(4) 0.5000 0.061(2) Uani 1 2 d S T P A .
O41 O 0.6767(6) 0.5036(5) 0.5654(3) 0.106(3) Uani 1 1 d . U . . .
N15 N 0.1334(5) 0.9385(3) 0.54510(18) 0.0253(11) Uani 1 1 d D . . . .
H15A H 0.103(7) 0.957(4) 0.5174(12) 0.038 Uiso 1 1 d D U . . .
H15B H 0.196(5) 0.900(3) 0.544(2) 0.038 Uiso 1 1 d D U . . .
H15C H 0.197(5) 0.969(3) 0.560(2) 0.038 Uiso 1 1 d D U . . .
C1 C 0.3364(6) 0.7439(3) 0.6510(2) 0.0281(14) Uani 1 1 d . . . . .
C2 C 0.2051(6) 0.7273(3) 0.6438(2) 0.0289(14) Uani 1 1 d . . . . .
C3 C 0.1141(6) 0.7808(4) 0.6323(2) 0.0307(15) Uani 1 1 d . . . . .
H3 H 0.0239 0.7695 0.6278 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1570(6) 0.8504(4) 0.6275(2) 0.0320(15) Uani 1 1 d . . . . .
C5 C 0.2884(7) 0.8665(4) 0.6332(2) 0.0338(15) Uani 1 1 d . . . . .
H5 H 0.3178 0.9138 0.6293 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3779(6) 0.8138(3) 0.6446(2) 0.0306(14) Uani 1 1 d . . . . .
C7 C 0.4796(10) 0.5979(5) 0.7334(3) 0.063(2) Uani 1 1 d . . . . .
C8 C 0.4948(18) 0.5412(6) 0.7014(4) 0.120(6) Uani 1 1 d . . . . .
H8A H 0.4247 0.5449 0.6791 0.144 Uiso 1 1 calc R U . . .
H8B H 0.4897 0.4950 0.7157 0.144 Uiso 1 1 calc R U . . .
H8C H 0.5803 0.5459 0.6881 0.144 Uiso 1 1 calc R U . . .
C9 C 0.5824(13) 0.5853(7) 0.7712(3) 0.091(4) Uani 1 1 d . . . . .
H9A H 0.6710 0.5853 0.7598 0.109 Uiso 1 1 calc R U . . .
H9B H 0.5654 0.5395 0.7848 0.109 Uiso 1 1 calc R U . . .
H9C H 0.5753 0.6232 0.7926 0.109 Uiso 1 1 calc R U . . .
C10 C 0.3389(11) 0.5981(6) 0.7505(4) 0.083(3) Uani 1 1 d . . . . .
H10A H 0.3161 0.5502 0.7601 0.100 Uiso 1 1 calc R U . . .
H10B H 0.2769 0.6130 0.7274 0.100 Uiso 1 1 calc R U . . .
H10C H 0.3343 0.6310 0.7748 0.100 Uiso 1 1 calc R U . . .
C11 C 0.6920(8) 0.6921(6) 0.6954(3) 0.067(3) Uani 1 1 d . . . . .
H11A H 0.7073 0.7348 0.6783 0.081 Uiso 1 1 calc R U . . .
H11B H 0.7156 0.6501 0.6788 0.081 Uiso 1 1 calc R U . . .
H11C H 0.7460 0.6939 0.7222 0.081 Uiso 1 1 calc R U . . .
C12 C 0.4695(8) 0.7591(4) 0.7465(3) 0.051(2) Uani 1 1 d . . . . .
H12A H 0.3738 0.7608 0.7485 0.061 Uiso 1 1 calc R U . . .
H12B H 0.5012 0.8046 0.7358 0.061 Uiso 1 1 calc R U . . .
H12C H 0.5095 0.7497 0.7751 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0415(7) 0.6370(4) 0.6419(3) 0.0476(19) Uani 1 1 d . . . . .
H13A H 0.0084 0.6561 0.6142 0.057 Uiso 1 1 calc R U . . .
H13B H -0.0112 0.6557 0.6652 0.057 Uiso 1 1 calc R U . . .
H13C H 0.0353 0.5852 0.6414 0.057 Uiso 1 1 calc R U . . .
C14 C 0.0575(7) 0.9085(4) 0.6179(2) 0.0375(16) Uani 1 1 d . . . . .
H14A H -0.0228 0.8980 0.6338 0.045 Uiso 1 1 calc R U . . .
H14B H 0.0937 0.9538 0.6292 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0196(6) 0.9185(4) 0.5713(2) 0.0302(14) Uani 1 1 d . . . . .
H15 H -0.0153 0.8723 0.5600 0.036 Uiso 1 1 calc R U . . .
C16 C -0.0898(6) 0.9744(3) 0.5653(2) 0.0280(14) Uani 1 1 d . . . . .
C17 C 0.5564(8) 0.8959(4) 0.6489(3) 0.048(2) Uani 1 1 d . . . . .
H17A H 0.5204 0.9231 0.6727 0.058 Uiso 1 1 calc R U . . .
H17B H 0.5282 0.9174 0.6213 0.058 Uiso 1 1 calc R U . . .
H17C H 0.6525 0.8962 0.6515 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6321(7) 0.8282(4) 0.5435(3) 0.0431(18) Uani 1 1 d . . . . .
H21A H 0.6229 0.8051 0.5152 0.052 Uiso 1 1 calc R U . . .
H21B H 0.6755 0.8742 0.5403 0.052 Uiso 1 1 calc R U . . .
H21C H 0.5451 0.8353 0.5553 0.052 Uiso 1 1 calc R U . . .
C22 C 0.6272(8) 0.6964(4) 0.5758(3) 0.051(2) Uani 1 1 d . . . . .
H22A H 0.6699 0.6573 0.5917 0.061 Uiso 1 1 calc R U . . .
H22B H 0.6137 0.6829 0.5455 0.061 Uiso 1 1 calc R U . . .
H22C H 0.5423 0.7067 0.5883 0.061 Uiso 1 1 calc R U . . .
C31 C 0.1435(8) 0.7057(4) 0.5247(3) 0.049(2) Uani 1 1 d . . . A -1
H31A H 0.0961 0.7044 0.4967 0.059 Uiso 1 1 calc R U . A -1
H31B H 0.0900 0.7303 0.5458 0.059 Uiso 1 1 calc R U . A -1
H31C H 0.1611 0.6572 0.5346 0.059 Uiso 1 1 calc R U . A -1
C41 C 0.8926(10) 0.4365(5) 0.5773(4) 0.075(3) Uani 1 1 d . U . . .
H41A H 0.8796 0.4185 0.5478 0.089 Uiso 1 1 calc R U . . .
H41B H 0.8568 0.4025 0.5977 0.089 Uiso 1 1 calc R U . . .
H41C H 0.9866 0.4430 0.5838 0.089 Uiso 1 1 calc R U . . .
C42 C 0.8934(7) 0.5610(4) 0.5393(3) 0.0474(19) Uani 1 1 d . U . . .
H42A H 0.8653 0.6107 0.5382 0.057 Uiso 1 1 calc R U . . .
H42B H 0.8702 0.5380 0.5117 0.057 Uiso 1 1 calc R U . . .
H42C H 0.9887 0.5588 0.5445 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S21 O21 1.501(5) . ?
S21 C22 1.783(8) . ?
S21 C21 1.792(8) . ?
S31 S31 1.428(7) 2_556 ?
S31 O31 1.564(7) . ?
S31 C31 1.705(8) . ?
S41 O41 1.487(7) . ?
S41 C41 1.719(10) . ?
S41 C42 1.789(8) . ?
Si1 O1 1.660(5) . ?
Si1 C12 1.860(8) . ?
Si1 C11 1.867(9) . ?
Si1 C7 1.890(9) . ?
O1 C1 1.378(7) . ?
O2 C2 1.364(8) . ?
O2 C13 1.421(8) . ?
O6 C6 1.367(8) . ?
O6 C17 1.432(8) . ?
O16 C16 1.248(8) . ?
O17 C16 1.245(8) . ?
O31 S31 1.564(7) 2_556 ?
N15 C15 1.486(8) . ?
N15 H15A 0.97(2) . ?
N15 H15B 0.97(2) . ?
N15 H15C 0.98(2) . ?
C1 C2 1.385(9) . ?
C1 C6 1.402(9) . ?
C2 C3 1.409(9) . ?
C3 C4 1.393(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(10) . ?
C4 C14 1.515(9) . ?
C5 C6 1.386(9) . ?
C5 H5 0.9500 . ?
C7 C8 1.471(14) . ?
C7 C10 1.545(15) . ?
C7 C9 1.563(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.494(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.542(9) . ?
C15 H15 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 S21 C22 105.0(4) . . ?
O21 S21 C21 107.1(3) . . ?
C22 S21 C21 97.2(4) . . ?
S31 S31 O31 62.85(17) 2_556 . ?
S31 S31 C31 68.2(4) 2_556 . ?
O31 S31 C31 105.3(4) . . ?
O41 S41 C41 105.4(5) . . ?
O41 S41 C42 105.4(4) . . ?
C41 S41 C42 97.0(5) . . ?
O1 Si1 C12 110.7(3) . . ?
O1 Si1 C11 108.7(3) . . ?
C12 Si1 C11 111.5(5) . . ?
O1 Si1 C7 106.4(4) . . ?
C12 Si1 C7 109.9(4) . . ?
C11 Si1 C7 109.4(5) . . ?
C1 O1 Si1 127.7(4) . . ?
C2 O2 C13 117.7(6) . . ?
C6 O6 C17 117.2(5) . . ?
S31 O31 S31 54.3(3) 2_556 . ?
C15 N15 H15A 110(4) . . ?
C15 N15 H15B 111(4) . . ?
H15A N15 H15B 116(6) . . ?
C15 N15 H15C 114(4) . . ?
H15A N15 H15C 114(6) . . ?
H15B N15 H15C 91(6) . . ?
O1 C1 C2 120.1(6) . . ?
O1 C1 C6 120.8(5) . . ?
C2 C1 C6 119.0(6) . . ?
O2 C2 C1 115.0(6) . . ?
O2 C2 C3 124.9(6) . . ?
C1 C2 C3 120.2(6) . . ?
C4 C3 C2 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 C14 120.4(6) . . ?
C3 C4 C14 119.5(6) . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
O6 C6 C5 124.5(6) . . ?
O6 C6 C1 114.7(5) . . ?
C5 C6 C1 120.8(6) . . ?
C8 C7 C10 110.6(11) . . ?
C8 C7 C9 108.2(10) . . ?
C10 C7 C9 110.5(9) . . ?
C8 C7 Si1 110.5(7) . . ?
C10 C7 Si1 109.2(6) . . ?
C9 C7 Si1 107.8(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C4 115.6(6) . . ?
C15 C14 H14A 108.4 . . ?
C4 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C4 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
N15 C15 C14 112.2(5) . . ?
N15 C15 C16 109.6(5) . . ?
C14 C15 C16 111.5(5) . . ?
N15 C15 H15 107.8 . . ?
C14 C15 H15 107.8 . . ?
C16 C15 H15 107.8 . . ?
O17 C16 O16 125.7(6) . . ?
O17 C16 C15 118.0(5) . . ?
O16 C16 C15 116.3(6) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S21 C21 H21A 109.5 . . ?
S21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S21 C22 H22A 109.5 . . ?
S21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S31 C31 H31A 109.5 . . ?
S31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
S31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
S41 C41 H41A 109.5 . . ?
S41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
S41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
S41 C42 H42A 109.5 . . ?
S41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
S41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

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
C12 Si1 O1 C1 6.3(6) . . . . ?
C11 Si1 O1 C1 -116.5(6) . . . . ?
C7 Si1 O1 C1 125.7(6) . . . . ?
C31 S31 O31 S31 -55.0(4) . . . 2_556 ?
Si1 O1 C1 C2 -118.0(6) . . . . ?
Si1 O1 C1 C6 63.3(8) . . . . ?
C13 O2 C2 C1 -179.8(6) . . . . ?
C13 O2 C2 C3 0.2(10) . . . . ?
O1 C1 C2 O2 -1.6(9) . . . . ?
C6 C1 C2 O2 177.1(6) . . . . ?
O1 C1 C2 C3 178.4(6) . . . . ?
C6 C1 C2 C3 -2.9(9) . . . . ?
O2 C2 C3 C4 -179.1(6) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C2 C3 C4 C5 1.2(9) . . . . ?
C2 C3 C4 C14 -176.1(6) . . . . ?
C3 C4 C5 C6 -1.3(10) . . . . ?
C14 C4 C5 C6 176.1(6) . . . . ?
C17 O6 C6 C5 6.2(10) . . . . ?
C17 O6 C6 C1 -173.7(6) . . . . ?
C4 C5 C6 O6 179.3(6) . . . . ?
C4 C5 C6 C1 -0.8(10) . . . . ?
O1 C1 C6 O6 1.5(9) . . . . ?
C2 C1 C6 O6 -177.2(6) . . . . ?
O1 C1 C6 C5 -178.4(6) . . . . ?
C2 C1 C6 C5 2.9(9) . . . . ?
O1 Si1 C7 C8 51.0(10) . . . . ?
C12 Si1 C7 C8 170.9(9) . . . . ?
C11 Si1 C7 C8 -66.3(10) . . . . ?
O1 Si1 C7 C10 -70.9(7) . . . . ?
C12 Si1 C7 C10 49.0(8) . . . . ?
C11 Si1 C7 C10 171.8(7) . . . . ?
O1 Si1 C7 C9 169.0(6) . . . . ?
C12 Si1 C7 C9 -71.1(8) . . . . ?
C11 Si1 C7 C9 51.7(8) . . . . ?
C5 C4 C14 C15 97.1(8) . . . . ?
C3 C4 C14 C15 -85.5(8) . . . . ?
C4 C14 C15 N15 -61.3(8) . . . . ?
C4 C14 C15 C16 175.4(6) . . . . ?
N15 C15 C16 O17 -1.1(8) . . . . ?
C14 C15 C16 O17 123.8(7) . . . . ?
N15 C15 C16 O16 177.4(6) . . . . ?
C14 C15 C16 O16 -57.7(8) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N15 H15A O17 . . . 2.642(7) 0.97(5) 2.33(6) 98(4) no
N15 H15A O17 . . 5_576 2.820(7) 0.97(5) 1.87(4) 166(6) no
N15 H15B O31 . . . 2.861(8) 0.97(5) 2.08(6) 137(6) no
N15 H15C O16 . . 6_675 2.814(7) 0.98(6) 1.84(6) 171(5) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
