# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_cu_scz48_0m
_database_code_depnum_ccdc_archive 'CCDC 1538431'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H26 O6, H2 O'
_chemical_formula_sum            'C19 H28 O7'
_chemical_formula_weight         368.41
_chemical_absolute_configuration unk

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4711(6)
_cell_length_b                   15.6577(15)
_cell_length_c                   9.2786(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.334(7)
_cell_angle_gamma                90.00
_cell_volume                     940.12(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5211
_cell_measurement_theta_min      5.54
_cell_measurement_theta_max      67.59

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.05
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4797
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5984
_diffrn_reflns_av_R_equivalents  0.1680
_diffrn_reflns_av_sigmaI/netI    0.1245
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.54
_diffrn_reflns_theta_max         69.08
_reflns_number_total             2577
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     240
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.1909
_refine_ls_wR_factor_ref         0.4274
_refine_ls_wR_factor_gt          0.4189
_refine_ls_goodness_of_fit_ref   1.932
_refine_ls_restrained_S_all      1.934
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.009

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O 0.4903(8) 0.9378(4) 0.4899(8) 0.0417(16) Uani 1 1 d . . .
O21 O 0.4065(10) 0.0158(7) -0.1901(9) 0.067(3) Uani 1 1 d . . .
O1 O 0.7180(8) 0.0543(4) -0.1152(7) 0.0335(14) Uani 1 1 d . . .
O7 O 1.2478(7) 0.0735(4) 0.4256(7) 0.0342(14) Uani 1 1 d . . .
H7 H 1.3490 0.0971 0.3856 0.051 Uiso 1 1 calc R . .
O6 O 0.9121(10) -0.0492(5) 0.4784(7) 0.0469(17) Uani 1 1 d . . .
H6 H 0.7845 -0.0479 0.4616 0.070 Uiso 1 1 calc R . .
O20 O 1.2053(7) 0.0471(3) 0.1875(7) 0.0305(13) Uani 1 1 d . . .
C20 C 1.0605(11) 0.0470(6) 0.0702(10) 0.0336(18) Uani 1 1 d . . .
H20A H 1.1177 0.0138 -0.0111 0.040 Uiso 1 1 calc R . .
H20B H 1.0377 0.1063 0.0367 0.040 Uiso 1 1 calc R . .
C21 C 0.5514(12) 0.0613(8) -0.1965(11) 0.045(2) Uani 1 1 d . . .
C1 C 0.7168(13) -0.0139(6) -0.0124(10) 0.040(2) Uani 1 1 d . . .
H1 H 0.5726 -0.0246 0.0213 0.049 Uiso 1 1 calc R . .
C10 C 0.8561(11) 0.0084(5) 0.1159(11) 0.0327(19) Uani 1 1 d . . .
C9 C 0.7567(10) 0.0799(5) 0.2170(10) 0.034(2) Uani 1 1 d . . .
H9 H 0.6535 0.0511 0.2803 0.041 Uiso 1 1 calc R . .
C11 C 0.6476(11) 0.1560(5) 0.1441(9) 0.0293(17) Uani 1 1 d . . .
H11A H 0.7401 0.1816 0.0714 0.035 Uiso 1 1 calc R . .
H11B H 0.5212 0.1358 0.0941 0.035 Uiso 1 1 calc R . .
C12 C 0.5902(13) 0.2228(7) 0.2552(12) 0.048(3) Uani 1 1 d . . .
H12A H 0.4852 0.1989 0.3211 0.057 Uiso 1 1 calc R . .
H12B H 0.5285 0.2728 0.2058 0.057 Uiso 1 1 calc R . .
C13 C 0.7790(17) 0.2519(8) 0.3433(14) 0.060(3) Uani 1 1 d . . .
O13 O 0.7968(15) 0.3301(7) 0.3806(13) 0.080(3) Uani 1 1 d . . .
C22 C 0.5828(15) 0.1323(8) -0.3095(13) 0.054(3) Uani 1 1 d . . .
H22A H 0.4704 0.1302 -0.3806 0.081 Uiso 1 1 calc R . .
H22B H 0.7153 0.1238 -0.3580 0.081 Uiso 1 1 calc R . .
H22C H 0.5827 0.1881 -0.2615 0.081 Uiso 1 1 calc R . .
C8 C 0.9270(11) 0.1112(5) 0.3108(9) 0.0298(17) Uani 1 1 d U . .
C7 C 1.1050(10) 0.0485(5) 0.3214(8) 0.0264(16) Uani 1 1 d . . .
C6 C 1.0226(10) -0.0435(5) 0.3452(8) 0.0279(17) Uani 1 1 d . . .
H6A H 1.1433 -0.0833 0.3501 0.033 Uiso 1 1 calc R . .
C5 C 0.8887(11) -0.0682(5) 0.2145(9) 0.0307(18) Uani 1 1 d . . .
H5 H 0.7492 -0.0812 0.2548 0.037 Uiso 1 1 calc R . .
C4 C 0.9599(18) -0.1522(7) 0.1413(13) 0.052(3) Uani 1 1 d . . .
C19 C 1.1924(18) -0.1511(8) 0.0867(15) 0.061(3) Uani 1 1 d . . .
H19A H 1.2374 -0.2096 0.0664 0.092 Uiso 1 1 calc R . .
H19B H 1.2816 -0.1261 0.1613 0.092 Uiso 1 1 calc R . .
H19C H 1.2015 -0.1168 -0.0014 0.092 Uiso 1 1 calc R . .
C18 C 0.942(2) -0.2262(7) 0.2520(18) 0.070(4) Uani 1 1 d . . .
H18A H 0.7987 -0.2314 0.2838 0.106 Uiso 1 1 calc R . .
H18B H 1.0315 -0.2142 0.3354 0.106 Uiso 1 1 calc R . .
H18C H 0.9858 -0.2798 0.2068 0.106 Uiso 1 1 calc R . .
C3 C 0.814(3) -0.1704(7) 0.0140(18) 0.083(5) Uani 1 1 d . . .
H3A H 0.6743 -0.1834 0.0510 0.099 Uiso 1 1 calc R . .
H3B H 0.8639 -0.2212 -0.0389 0.099 Uiso 1 1 calc R . .
C2 C 0.801(2) -0.0940(8) -0.0899(14) 0.061(3) Uani 1 1 d . . .
H2A H 0.7094 -0.1086 -0.1721 0.073 Uiso 1 1 calc R . .
H2B H 0.9403 -0.0816 -0.1285 0.073 Uiso 1 1 calc R . .
C14 C 0.9407(15) 0.1907(7) 0.3676(11) 0.047(2) Uani 1 1 d . . .
H14 H 1.0580 0.2061 0.4239 0.056 Uiso 1 1 calc R . .


_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
O21 C21 1.180(13) . ?
O1 C21 1.317(11) . ?
O1 C1 1.432(10) . ?
O7 C7 1.389(9) . ?
O7 H7 0.8400 . ?
O6 C6 1.434(11) . ?
O6 H6 0.8400 . ?
O20 C7 1.405(10) . ?
O20 C20 1.432(10) . ?
C20 C10 1.517(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.542(17) . ?
C1 C10 1.529(12) . ?
C1 C2 1.547(16) . ?
C1 H1 1.0000 . ?
C10 C5 1.523(10) . ?
C10 C9 1.599(13) . ?
C9 C8 1.483(12) . ?
C9 C11 1.539(10) . ?
C9 H9 1.0000 . ?
C11 C12 1.516(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.535(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O13 1.278(15) . ?
C13 C14 1.435(13) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C8 C14 1.356(13) . ?
C8 C7 1.516(9) . ?
C7 C6 1.553(10) . ?
C6 C5 1.535(10) . ?
C6 H6A 1.0000 . ?
C5 C4 1.551(13) . ?
C5 H5 1.0000 . ?
C4 C3 1.535(15) . ?
C4 C18 1.554(17) . ?
C4 C19 1.590(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 C2 1.538(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 H14 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
C21 O1 C1 115.9(7) . . ?
C7 O7 H7 109.5 . . ?
C6 O6 H6 109.5 . . ?
C7 O20 C20 111.6(5) . . ?
O20 C20 C10 110.8(7) . . ?
O20 C20 H20A 109.5 . . ?
C10 C20 H20A 109.5 . . ?
O20 C20 H20B 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O21 C21 O1 124.7(11) . . ?
O21 C21 C22 125.3(9) . . ?
O1 C21 C22 109.8(8) . . ?
O1 C1 C10 110.0(6) . . ?
O1 C1 C2 106.9(8) . . ?
C10 C1 C2 109.8(8) . . ?
O1 C1 H1 110.0 . . ?
C10 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C20 C10 C5 111.4(6) . . ?
C20 C10 C1 112.6(7) . . ?
C5 C10 C1 111.5(7) . . ?
C20 C10 C9 103.8(7) . . ?
C5 C10 C9 104.7(7) . . ?
C1 C10 C9 112.3(7) . . ?
C8 C9 C11 109.9(7) . . ?
C8 C9 C10 106.0(6) . . ?
C11 C9 C10 118.0(7) . . ?
C8 C9 H9 107.5 . . ?
C11 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C12 C11 C9 110.4(7) . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 111.7(6) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O13 C13 C14 122.2(10) . . ?
O13 C13 C12 119.9(9) . . ?
C14 C13 C12 117.6(9) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C8 C9 125.3(7) . . ?
C14 C8 C7 121.4(7) . . ?
C9 C8 C7 112.7(7) . . ?
O7 C7 O20 108.1(5) . . ?
O7 C7 C8 111.4(6) . . ?
O20 C7 C8 107.9(6) . . ?
O7 C7 C6 112.9(6) . . ?
O20 C7 C6 105.8(6) . . ?
C8 C7 C6 110.3(6) . . ?
O6 C6 C5 112.5(6) . . ?
O6 C6 C7 110.7(7) . . ?
C5 C6 C7 108.3(6) . . ?
O6 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C10 C5 C6 110.6(7) . . ?
C10 C5 C4 116.4(8) . . ?
C6 C5 C4 113.1(7) . . ?
C10 C5 H5 105.2 . . ?
C6 C5 H5 105.2 . . ?
C4 C5 H5 105.2 . . ?
C3 C4 C5 108.2(9) . . ?
C3 C4 C18 108.8(9) . . ?
C5 C4 C18 108.7(10) . . ?
C3 C4 C19 109.6(12) . . ?
C5 C4 C19 114.5(9) . . ?
C18 C4 C19 107.0(10) . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C3 C2 111.6(10) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C2 C1 110.9(11) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C8 C14 C13 120.4(8) . . ?
C8 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O20 C20 C10 -26.2(9) . . . . ?
C1 O1 C21 O21 -0.4(14) . . . . ?
C1 O1 C21 C22 -175.3(8) . . . . ?
C21 O1 C1 C10 -153.2(7) . . . . ?
C21 O1 C1 C2 87.6(9) . . . . ?
O20 C20 C10 C5 -39.3(10) . . . . ?
O20 C20 C10 C1 -165.4(7) . . . . ?
O20 C20 C10 C9 72.9(8) . . . . ?
O1 C1 C10 C20 -44.0(10) . . . . ?
C2 C1 C10 C20 73.4(9) . . . . ?
O1 C1 C10 C5 -170.1(7) . . . . ?
C2 C1 C10 C5 -52.6(10) . . . . ?
O1 C1 C10 C9 72.7(8) . . . . ?
C2 C1 C10 C9 -169.8(8) . . . . ?
C20 C10 C9 C8 -43.3(8) . . . . ?
C5 C10 C9 C8 73.6(7) . . . . ?
C1 C10 C9 C8 -165.3(7) . . . . ?
C20 C10 C9 C11 80.3(8) . . . . ?
C5 C10 C9 C11 -162.8(6) . . . . ?
C1 C10 C9 C11 -41.7(9) . . . . ?
C8 C9 C11 C12 -50.4(9) . . . . ?
C10 C9 C11 C12 -172.0(7) . . . . ?
C9 C11 C12 C13 55.3(12) . . . . ?
C11 C12 C13 O13 142.5(13) . . . . ?
C11 C12 C13 C14 -31.0(17) . . . . ?
C11 C9 C8 C14 22.6(12) . . . . ?
C10 C9 C8 C14 151.2(9) . . . . ?
C11 C9 C8 C7 -149.1(7) . . . . ?
C10 C9 C8 C7 -20.6(9) . . . . ?
C20 O20 C7 O7 -162.8(6) . . . . ?
C20 O20 C7 C8 -42.1(8) . . . . ?
C20 O20 C7 C6 76.0(7) . . . . ?
C14 C8 C7 O7 16.6(12) . . . . ?
C9 C8 C7 O7 -171.3(6) . . . . ?
C14 C8 C7 O20 -102.0(10) . . . . ?
C9 C8 C7 O20 70.1(8) . . . . ?
C14 C8 C7 C6 142.9(9) . . . . ?
C9 C8 C7 C6 -45.0(9) . . . . ?
O7 C7 C6 O6 63.3(7) . . . . ?
O20 C7 C6 O6 -178.7(5) . . . . ?
C8 C7 C6 O6 -62.2(8) . . . . ?
O7 C7 C6 C5 -172.9(6) . . . . ?
O20 C7 C6 C5 -54.8(7) . . . . ?
C8 C7 C6 C5 61.7(8) . . . . ?
C20 C10 C5 C6 55.3(10) . . . . ?
C1 C10 C5 C6 -178.0(7) . . . . ?
C9 C10 C5 C6 -56.3(8) . . . . ?
C20 C10 C5 C4 -75.6(10) . . . . ?
C1 C10 C5 C4 51.2(9) . . . . ?
C9 C10 C5 C4 172.9(7) . . . . ?
O6 C6 C5 C10 114.9(7) . . . . ?
C7 C6 C5 C10 -7.8(9) . . . . ?
O6 C6 C5 C4 -112.5(8) . . . . ?
C7 C6 C5 C4 124.7(8) . . . . ?
C10 C5 C4 C3 -50.8(13) . . . . ?
C6 C5 C4 C3 179.5(10) . . . . ?
C10 C5 C4 C18 -168.8(7) . . . . ?
C6 C5 C4 C18 61.5(10) . . . . ?
C10 C5 C4 C19 71.7(11) . . . . ?
C6 C5 C4 C19 -58.0(11) . . . . ?
C5 C4 C3 C2 54.4(17) . . . . ?
C18 C4 C3 C2 172.3(13) . . . . ?
C19 C4 C3 C2 -71.1(15) . . . . ?
C4 C3 C2 C1 -60.8(17) . . . . ?
O1 C1 C2 C3 177.8(8) . . . . ?
C10 C1 C2 C3 58.4(11) . . . . ?
C9 C8 C14 C13 2.4(17) . . . . ?
C7 C8 C14 C13 173.4(10) . . . . ?
O13 C13 C14 C8 -171.7(13) . . . . ?
C12 C13 C14 C8 1.7(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        69.08
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         1.515
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.246
####################################################################### 
# 
# 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_cu_scz21_0m
_database_code_depnum_ccdc_archive 'CCDC 1538442'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 O4, H2 O'
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.46
_chemical_absolute_configuration ad

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.60840(10)
_cell_length_b                   11.8396(2)
_cell_length_c                   22.9114(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1792.61(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      4.20
_cell_measurement_theta_max      69.29

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          2.00
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3173
_exptl_absorpt_correction_T_max  0.8414
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10748
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         69.52
_reflns_number_total             3144
_reflns_number_gt                3141
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0408P)²+0.4287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_number_reflns         3144
_refine_ls_number_parameters     237
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O19 O 1.10863(16) 0.38956(9) 0.33121(4) 0.0194(2) Uani 1 1 d . . .
H19 H 1.2003 0.3405 0.3325 0.029 Uiso 1 1 calc R . .
O1S O 0.06486(15) 0.77112(8) 0.07122(4) 0.0154(2) Uani 1 1 d D . .
H1SB H 0.135(3) 0.8079(13) 0.0483(6) 0.023 Uiso 1 1 d D . .
H1SA H 0.019(3) 0.8132(13) 0.0961(6) 0.023 Uiso 1 1 d D . .
O7 O 0.64962(15) 0.71169(7) 0.13172(4) 0.0146(2) Uani 1 1 d . . .
O14 O 0.80465(15) 0.63121(8) 0.01189(4) 0.0141(2) Uani 1 1 d . . .
H14 H 0.8755 0.6763 0.0315 0.021 Uiso 1 1 calc R . .
O15 O 0.26383(14) 0.57242(8) 0.09936(4) 0.0146(2) Uani 1 1 d . . .
H15 H 0.2058 0.6355 0.0979 0.022 Uiso 1 1 calc R . .
C19 C 1.0416(2) 0.40315(11) 0.27192(6) 0.0159(3) Uani 1 1 d . . .
H19A H 1.0769 0.3352 0.2489 0.019 Uiso 1 1 calc R . .
H19B H 1.1097 0.4691 0.2540 0.019 Uiso 1 1 calc R . .
C4 C 0.8120(2) 0.42079(11) 0.27127(6) 0.0141(3) Uani 1 1 d . . .
C5 C 0.7253(2) 0.45538(10) 0.21042(6) 0.0122(3) Uani 1 1 d . . .
H5 H 0.5800 0.4732 0.2183 0.015 Uiso 1 1 calc R . .
C10 C 0.7181(2) 0.36322(10) 0.16192(6) 0.0130(3) Uani 1 1 d . . .
C9 C 0.5712(2) 0.41009(10) 0.11491(6) 0.0124(3) Uani 1 1 d . . .
H9 H 0.4402 0.4210 0.1360 0.015 Uiso 1 1 calc R . .
C11 C 0.5196(2) 0.32739(11) 0.06431(6) 0.0163(3) Uani 1 1 d . . .
H11A H 0.6186 0.2646 0.0638 0.020 Uiso 1 1 calc R . .
H11B H 0.3833 0.2949 0.0705 0.020 Uiso 1 1 calc R . .
C12 C 0.5254(2) 0.39011(11) 0.00555(6) 0.0164(3) Uani 1 1 d . . .
H12 H 0.4864 0.3379 -0.0269 0.020 Uiso 1 1 calc R . .
C16 C 0.3851(2) 0.49080(11) 0.00700(6) 0.0145(3) Uani 1 1 d . . .
C17 C 0.2471(2) 0.51267(13) -0.03329(6) 0.0194(3) Uani 1 1 d . . .
H17A H 0.2317 0.4635 -0.0657 0.023 Uiso 1 1 calc R . .
H17B H 0.1635 0.5776 -0.0298 0.023 Uiso 1 1 calc R . .
C20 C 0.9275(2) 0.33150(11) 0.13738(6) 0.0159(3) Uani 1 1 d . . .
H20A H 0.9946 0.2789 0.1641 0.024 Uiso 1 1 calc R . .
H20B H 1.0099 0.3998 0.1333 0.024 Uiso 1 1 calc R . .
H20C H 0.9111 0.2956 0.0991 0.024 Uiso 1 1 calc R . .
C1 C 0.6160(2) 0.25617(11) 0.18723(6) 0.0173(3) Uani 1 1 d . . .
H1A H 0.4703 0.2717 0.1933 0.021 Uiso 1 1 calc R . .
H1B H 0.6275 0.1941 0.1585 0.021 Uiso 1 1 calc R . .
C2 C 0.7090(2) 0.21767(11) 0.24501(6) 0.0195(3) Uani 1 1 d . . .
H2A H 0.6342 0.1512 0.2599 0.023 Uiso 1 1 calc R . .
H2B H 0.8515 0.1950 0.2386 0.023 Uiso 1 1 calc R . .
C3 C 0.7010(2) 0.31201(12) 0.28998(6) 0.0179(3) Uani 1 1 d . . .
H3A H 0.7614 0.2844 0.3268 0.021 Uiso 1 1 calc R . .
H3B H 0.5575 0.3306 0.2979 0.021 Uiso 1 1 calc R . .
C8 C 0.6213(2) 0.52851(10) 0.08911(5) 0.0112(3) Uani 1 1 d . . .
C7 C 0.6878(2) 0.61141(11) 0.13583(5) 0.0108(3) Uani 1 1 d . . .
C6 C 0.8130(2) 0.56627(11) 0.18585(6) 0.0136(3) Uani 1 1 d . . .
H6A H 0.8182 0.6235 0.2173 0.016 Uiso 1 1 calc R . .
H6B H 0.9531 0.5528 0.1722 0.016 Uiso 1 1 calc R . .
C14 C 0.7923(2) 0.52501(10) 0.04181(6) 0.0123(3) Uani 1 1 d . . .
H14A H 0.9250 0.5076 0.0607 0.015 Uiso 1 1 calc R . .
C13 C 0.7417(2) 0.43325(12) -0.00352(6) 0.0165(3) Uani 1 1 d . . .
H13A H 0.7553 0.4648 -0.0433 0.020 Uiso 1 1 calc R . .
H13B H 0.8382 0.3697 0.0004 0.020 Uiso 1 1 calc R . .
C15 C 0.4276(2) 0.57029(11) 0.05829(5) 0.0125(3) Uani 1 1 d . . .
H15A H 0.4508 0.6484 0.0431 0.015 Uiso 1 1 calc R . .
C18 C 0.7589(2) 0.51322(12) 0.31600(6) 0.0194(3) Uani 1 1 d . . .
H18A H 0.7869 0.4855 0.3555 0.029 Uiso 1 1 calc R . .
H18B H 0.6151 0.5324 0.3126 0.029 Uiso 1 1 calc R . .
H18C H 0.8409 0.5806 0.3083 0.029 Uiso 1 1 calc R . .


_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
O19 C19 1.4379(16) . ?
O19 H19 0.8400 . ?
O1S H1SB 0.826(9) . ?
O1S H1SA 0.815(9) . ?
O7 C7 1.2174(16) . ?
O14 C14 1.4344(15) . ?
O14 H14 0.8400 . ?
O15 C15 1.4341(16) . ?
O15 H15 0.8400 . ?
C19 C4 1.531(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C4 C18 1.5399(18) . ?
C4 C3 1.5430(19) . ?
C4 C5 1.5619(17) . ?
C5 C6 1.5416(17) . ?
C5 C10 1.5581(17) . ?
C5 H5 1.0000 . ?
C10 C20 1.540(2) . ?
C10 C1 1.5485(17) . ?
C10 C9 1.5523(18) . ?
C9 C11 1.5555(18) . ?
C9 C8 1.5572(16) . ?
C9 H9 1.0000 . ?
C11 C12 1.5380(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.511(2) . ?
C12 C13 1.533(2) . ?
C12 H12 1.0000 . ?
C16 C17 1.323(2) . ?
C16 C15 1.5315(18) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C1 C2 1.5291(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C8 C7 1.5173(17) . ?
C8 C15 1.5436(18) . ?
C8 C14 1.5664(18) . ?
C7 C6 1.5111(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14 C13 1.5397(17) . ?
C14 H14A 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 1.0000 . ?
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
C19 O19 H19 109.5 . . ?
H1SB O1S H1SA 109.3(15) . . ?
C14 O14 H14 109.5 . . ?
C15 O15 H15 109.5 . . ?
O19 C19 C4 109.24(11) . . ?
O19 C19 H19A 109.8 . . ?
C4 C19 H19A 109.8 . . ?
O19 C19 H19B 109.8 . . ?
C4 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C19 C4 C18 108.45(12) . . ?
C19 C4 C3 110.78(11) . . ?
C18 C4 C3 107.45(11) . . ?
C19 C4 C5 114.06(11) . . ?
C18 C4 C5 108.90(11) . . ?
C3 C4 C5 106.99(11) . . ?
C6 C5 C10 110.33(10) . . ?
C6 C5 C4 114.30(11) . . ?
C10 C5 C4 117.66(10) . . ?
C6 C5 H5 104.3 . . ?
C10 C5 H5 104.3 . . ?
C4 C5 H5 104.3 . . ?
C20 C10 C1 109.18(11) . . ?
C20 C10 C9 113.31(11) . . ?
C1 C10 C9 106.27(11) . . ?
C20 C10 C5 113.80(11) . . ?
C1 C10 C5 108.63(10) . . ?
C9 C10 C5 105.29(10) . . ?
C10 C9 C11 115.42(10) . . ?
C10 C9 C8 116.90(11) . . ?
C11 C9 C8 109.29(10) . . ?
C10 C9 H9 104.6 . . ?
C11 C9 H9 104.6 . . ?
C8 C9 H9 104.6 . . ?
C12 C11 C9 110.07(10) . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C16 C12 C13 108.22(11) . . ?
C16 C12 C11 110.28(11) . . ?
C13 C12 C11 107.62(12) . . ?
C16 C12 H12 110.2 . . ?
C13 C12 H12 110.2 . . ?
C11 C12 H12 110.2 . . ?
C17 C16 C12 124.19(12) . . ?
C17 C16 C15 122.78(13) . . ?
C12 C16 C15 112.91(11) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 C1 C10 113.16(12) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 110.70(11) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 114.10(11) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C7 C8 C15 110.83(10) . . ?
C7 C8 C9 112.09(10) . . ?
C15 C8 C9 106.62(11) . . ?
C7 C8 C14 107.24(11) . . ?
C15 C8 C14 106.88(10) . . ?
C9 C8 C14 113.09(10) . . ?
O7 C7 C6 121.14(11) . . ?
O7 C7 C8 121.08(11) . . ?
C6 C7 C8 117.69(11) . . ?
C7 C6 C5 111.87(11) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O14 C14 C13 107.97(10) . . ?
O14 C14 C8 110.40(10) . . ?
C13 C14 C8 109.20(11) . . ?
O14 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C8 C14 H14A 109.7 . . ?
C12 C13 C14 110.25(11) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O15 C15 C16 112.08(11) . . ?
O15 C15 C8 109.34(10) . . ?
C16 C15 C8 107.83(11) . . ?
O15 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C8 C15 H15A 109.2 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 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
O19 C19 C4 C18 49.37(14) . . . . ?
O19 C19 C4 C3 -68.32(14) . . . . ?
O19 C19 C4 C5 170.90(10) . . . . ?
C19 C4 C5 C6 -59.66(15) . . . . ?
C18 C4 C5 C6 61.62(15) . . . . ?
C3 C4 C5 C6 177.47(11) . . . . ?
C19 C4 C5 C10 72.18(15) . . . . ?
C18 C4 C5 C10 -166.54(12) . . . . ?
C3 C4 C5 C10 -50.69(15) . . . . ?
C6 C5 C10 C20 61.95(14) . . . . ?
C4 C5 C10 C20 -71.65(15) . . . . ?
C6 C5 C10 C1 -176.21(11) . . . . ?
C4 C5 C10 C1 50.18(16) . . . . ?
C6 C5 C10 C9 -62.72(14) . . . . ?
C4 C5 C10 C9 163.67(12) . . . . ?
C20 C10 C9 C11 61.29(15) . . . . ?
C1 C10 C9 C11 -58.60(14) . . . . ?
C5 C10 C9 C11 -173.73(11) . . . . ?
C20 C10 C9 C8 -69.35(14) . . . . ?
C1 C10 C9 C8 170.77(11) . . . . ?
C5 C10 C9 C8 55.64(14) . . . . ?
C10 C9 C11 C12 -136.68(12) . . . . ?
C8 C9 C11 C12 -2.49(16) . . . . ?
C9 C11 C12 C16 -55.62(15) . . . . ?
C9 C11 C12 C13 62.23(14) . . . . ?
C13 C12 C16 C17 113.03(15) . . . . ?
C11 C12 C16 C17 -129.50(15) . . . . ?
C13 C12 C16 C15 -63.27(14) . . . . ?
C11 C12 C16 C15 54.20(15) . . . . ?
C20 C10 C1 C2 73.48(14) . . . . ?
C9 C10 C1 C2 -163.98(12) . . . . ?
C5 C10 C1 C2 -51.13(15) . . . . ?
C10 C1 C2 C3 56.77(16) . . . . ?
C1 C2 C3 C4 -58.79(16) . . . . ?
C19 C4 C3 C2 -71.33(15) . . . . ?
C18 C4 C3 C2 170.37(12) . . . . ?
C5 C4 C3 C2 53.55(15) . . . . ?
C10 C9 C8 C7 -42.48(16) . . . . ?
C11 C9 C8 C7 -175.92(11) . . . . ?
C10 C9 C8 C15 -163.92(11) . . . . ?
C11 C9 C8 C15 62.64(13) . . . . ?
C10 C9 C8 C14 78.90(14) . . . . ?
C11 C9 C8 C14 -54.53(15) . . . . ?
C15 C8 C7 O7 -28.52(17) . . . . ?
C9 C8 C7 O7 -147.51(12) . . . . ?
C14 C8 C7 O7 87.80(15) . . . . ?
C15 C8 C7 C6 154.87(11) . . . . ?
C9 C8 C7 C6 35.87(17) . . . . ?
C14 C8 C7 C6 -88.81(13) . . . . ?
O7 C7 C6 C5 137.80(13) . . . . ?
C8 C7 C6 C5 -45.58(16) . . . . ?
C10 C5 C6 C7 59.68(14) . . . . ?
C4 C5 C6 C7 -165.05(11) . . . . ?
C7 C8 C14 O14 -67.01(13) . . . . ?
C15 C8 C14 O14 51.89(13) . . . . ?
C9 C8 C14 O14 168.91(11) . . . . ?
C7 C8 C14 C13 174.44(11) . . . . ?
C15 C8 C14 C13 -66.66(13) . . . . ?
C9 C8 C14 C13 50.35(14) . . . . ?
C16 C12 C13 C14 52.15(14) . . . . ?
C11 C12 C13 C14 -67.01(13) . . . . ?
O14 C14 C13 C12 -109.86(12) . . . . ?
C8 C14 C13 C12 10.20(14) . . . . ?
C17 C16 C15 O15 69.80(17) . . . . ?
C12 C16 C15 O15 -113.84(12) . . . . ?
C17 C16 C15 C8 -169.81(13) . . . . ?
C12 C16 C15 C8 6.55(15) . . . . ?
C7 C8 C15 O15 -64.93(13) . . . . ?
C9 C8 C15 O15 57.31(13) . . . . ?
C14 C8 C15 O15 178.52(9) . . . . ?
C7 C8 C15 C16 172.97(10) . . . . ?
C9 C8 C15 C16 -64.79(13) . . . . ?
C14 C8 C15 C16 56.42(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O19 H19 O7 0.84 1.99 2.7764(13) 154.4 3_745
O1S H1SB O14 0.826(9) 1.917(9) 2.7338(13) 170.1(17) 2_465
O1S H1SA O19 0.815(9) 2.075(9) 2.8773(14) 168.1(17) 3_655
O14 H14 O1S 0.84 1.91 2.7475(13) 173.0 1_655
O15 H15 O1S 0.84 1.95 2.7711(14) 163.9 .

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        69.52
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.066
