# Electronic Supplementary Material (ESI) for ChemComm.
# 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_triflate
_database_code_depnum_ccdc_archive 'CCDC 1532609'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H31 F3 O12 S'
_chemical_formula_sum            'C19 H31 F3 O12 S'
_chemical_formula_weight         540.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn '

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

_cell_length_a                   19.882(2)
_cell_length_b                   11.2489(12)
_cell_length_c                   24.609(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.666(5)
_cell_angle_gamma                90.00
_cell_volume                     5115.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3046
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      20.61

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.403
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8862
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8862
_reflns_number_gt                4854
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.1412P)²+31.9721P] 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     SHELXL
_refine_ls_extinction_coef       0.0051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8862
_refine_ls_number_parameters     696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1996
_refine_ls_R_factor_gt           0.1276
_refine_ls_wR_factor_ref         0.3736
_refine_ls_wR_factor_gt          0.3425
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.5222(4) 0.8560(6) 0.2650(3) 0.0374(17) Uani 1 1 d . . .
H1A H 0.5736 0.8652 0.2718 0.045 Uiso 1 1 calc R . .
C2A C 0.4809(4) 0.8268(6) 0.2022(3) 0.0341(17) Uani 1 1 d . . .
H2A H 0.5017 0.7551 0.1921 0.041 Uiso 1 1 calc R . .
C3A C 0.4015(4) 0.8054(6) 0.1893(3) 0.0354(17) Uani 1 1 d . . .
H3A H 0.3799 0.8786 0.1971 0.043 Uiso 1 1 calc R . .
C4A C 0.3902(4) 0.7058(6) 0.2270(3) 0.0352(17) Uani 1 1 d . . .
H4A H 0.4039 0.6285 0.2158 0.042 Uiso 1 1 calc R . .
C5A C 0.4324(4) 0.7329(6) 0.2894(3) 0.0342(16) Uani 1 1 d . . .
H5A H 0.4126 0.8050 0.3002 0.041 Uiso 1 1 calc R . .
C6A C 0.5119(4) 0.7530(6) 0.3011(3) 0.0346(17) Uani 1 1 d . . .
H6A H 0.5325 0.6807 0.2913 0.041 Uiso 1 1 calc R . .
C7A C 0.4499(4) 0.8968(6) 0.1047(3) 0.0406(18) Uani 1 1 d . . .
C8A C 0.4599(5) 1.0076(8) 0.0729(4) 0.061(2) Uani 1 1 d . . .
H8A1 H 0.4378 1.0743 0.0841 0.092 Uiso 1 1 calc R . .
H8A2 H 0.4375 0.9955 0.0315 0.092 Uiso 1 1 calc R . .
H8A3 H 0.5106 1.0227 0.0832 0.092 Uiso 1 1 calc R . .
C9A C 0.5581(5) 0.7989(9) 0.1039(4) 0.066(3) Uani 1 1 d . . .
H9A1 H 0.5737 0.7262 0.0918 0.098 Uiso 1 1 calc R . .
H9A2 H 0.5822 0.8086 0.1453 0.098 Uiso 1 1 calc R . .
H9A3 H 0.5698 0.8646 0.0840 0.098 Uiso 1 1 calc R . .
C10A C 0.3703(4) 0.8634(7) 0.0898(4) 0.0453(19) Uani 1 1 d . . .
C11A C 0.3339(5) 0.8132(8) 0.0287(4) 0.063(2) Uani 1 1 d . . .
H11A H 0.3585 0.7420 0.0249 0.095 Uiso 1 1 calc R . .
H11B H 0.3360 0.8707 0.0005 0.095 Uiso 1 1 calc R . .
H11C H 0.2843 0.7951 0.0220 0.095 Uiso 1 1 calc R . .
C12A C 0.2623(5) 0.9594(10) 0.0903(5) 0.078(3) Uani 1 1 d . . .
H12A H 0.2447 1.0351 0.0972 0.116 Uiso 1 1 calc R . .
H12B H 0.2568 0.9020 0.1172 0.116 Uiso 1 1 calc R . .
H12C H 0.2353 0.9343 0.0510 0.116 Uiso 1 1 calc R . .
C13A C 0.4584(4) 0.6606(7) 0.3850(3) 0.0449(19) Uani 1 1 d . . .
C14A C 0.3525(5) 0.7663(10) 0.3861(5) 0.073(3) Uani 1 1 d . . .
H14A H 0.3387 0.8400 0.3987 0.109 Uiso 1 1 calc R . .
H14B H 0.3389 0.7013 0.4052 0.109 Uiso 1 1 calc R . .
H14C H 0.3286 0.7586 0.3445 0.109 Uiso 1 1 calc R . .
C15A C 0.4466(6) 0.5520(9) 0.4162(4) 0.069(3) Uani 1 1 d . . .
H15A H 0.4688 0.5635 0.4576 0.104 Uiso 1 1 calc R . .
H15B H 0.4677 0.4840 0.4050 0.104 Uiso 1 1 calc R . .
H15C H 0.3956 0.5391 0.4056 0.104 Uiso 1 1 calc R . .
C16A C 0.5393(4) 0.6914(7) 0.3996(4) 0.047(2) Uani 1 1 d . . .
C17A C 0.5766(5) 0.7402(8) 0.4613(4) 0.059(2) Uani 1 1 d . . .
H17A H 0.5721 0.6839 0.4891 0.089 Uiso 1 1 calc R . .
H17B H 0.5542 0.8138 0.4650 0.089 Uiso 1 1 calc R . .
H17C H 0.6268 0.7537 0.4686 0.089 Uiso 1 1 calc R . .
C18A C 0.6455(6) 0.5831(10) 0.4031(5) 0.087(4) Uani 1 1 d . . .
H18A H 0.6607 0.5053 0.3963 0.131 Uiso 1 1 calc R . .
H18B H 0.6712 0.6052 0.4431 0.131 Uiso 1 1 calc R . .
H18C H 0.6556 0.6394 0.3778 0.131 Uiso 1 1 calc R . .
C19A C 0.2236(9) 0.5634(16) 0.2364(7) 0.107(5) Uani 1 1 d . . .
O1A O 0.4946(3) 0.9636(4) 0.2785(2) 0.0511(15) Uani 1 1 d . . .
H1A1 H 0.5167 0.9805 0.3129 0.077 Uiso 1 1 calc R . .
O2A O 0.4856(3) 0.9216(4) 0.1654(2) 0.0397(12) Uani 1 1 d . . .
O3A O 0.3652(3) 0.7727(4) 0.1297(2) 0.0415(13) Uani 1 1 d . . .
O4A O 0.3124(3) 0.7079(5) 0.2192(2) 0.0509(15) Uani 1 1 d . . .
O5A O 0.4241(3) 0.6367(4) 0.3241(2) 0.0424(13) Uani 1 1 d . . .
O6A O 0.5482(3) 0.7790(5) 0.3617(2) 0.0444(13) Uani 1 1 d . . .
O7A O 0.4818(3) 0.7951(5) 0.0896(2) 0.0512(15) Uani 1 1 d . . .
O8A O 0.3366(3) 0.9693(5) 0.0985(3) 0.0573(16) Uani 1 1 d . . .
O9A O 0.4293(3) 0.7648(5) 0.4010(2) 0.0507(14) Uani 1 1 d . . .
O10A O 0.5703(3) 0.5818(5) 0.3914(2) 0.0536(15) Uani 1 1 d . . .
O11A O 0.2850(6) 0.5279(11) 0.1624(6) 0.168(6) Uani 1 1 d . . .
O12A O 0.1957(5) 0.6810(12) 0.1432(5) 0.161(5) Uani 1 1 d . . .
F1A F 0.2046(7) 0.6494(13) 0.2631(6) 0.193(6) Uani 1 1 d . . .
F2A F 0.2772(6) 0.5124(12) 0.2784(5) 0.202(6) Uani 1 1 d . . .
F3A F 0.1716(4) 0.4876(8) 0.2147(4) 0.139(3) Uani 1 1 d . . .
S1A S 0.25534(14) 0.6191(3) 0.18293(13) 0.0781(9) Uani 1 1 d . . .
C1B C 0.4884(4) 0.3546(6) 0.2623(3) 0.0367(17) Uani 1 1 d . . .
H1B H 0.4406 0.3620 0.2650 0.044 Uiso 1 1 calc R . .
C2B C 0.4795(4) 0.3239(6) 0.2007(3) 0.0341(16) Uani 1 1 d . . .
H2B H 0.4507 0.2510 0.1892 0.041 Uiso 1 1 calc R . .
C3B C 0.5516(4) 0.3047(6) 0.1942(3) 0.0346(17) Uani 1 1 d . . .
H3B H 0.5800 0.3782 0.2042 0.042 Uiso 1 1 calc R . .
C4B C 0.5930(4) 0.2067(7) 0.2328(3) 0.0392(18) Uani 1 1 d . A .
H4B H 0.5694 0.1297 0.2200 0.047 Uiso 1 1 calc R . .
C5B C 0.6028(4) 0.2329(7) 0.2959(3) 0.0392(18) Uani 1 1 d . . .
H5B H 0.6317 0.3054 0.3085 0.047 Uiso 1 1 calc R . .
C6B C 0.5303(4) 0.2515(7) 0.3020(3) 0.0401(18) Uani 1 1 d . . .
H6B H 0.5017 0.1784 0.2907 0.048 Uiso 1 1 calc R . .
C7B C 0.4296(4) 0.3961(7) 0.1029(3) 0.0440(19) Uani 1 1 d . . .
C8B C 0.3188(5) 0.2943(10) 0.0902(5) 0.082(3) Uani 1 1 d . . .
H8B1 H 0.2939 0.2210 0.0757 0.123 Uiso 1 1 calc R . .
H8B2 H 0.2902 0.3596 0.0686 0.123 Uiso 1 1 calc R . .
H8B3 H 0.3263 0.3029 0.1308 0.123 Uiso 1 1 calc R . .
C9B C 0.3949(5) 0.5064(7) 0.0706(4) 0.060(2) Uani 1 1 d . . .
H9B1 H 0.4266 0.5729 0.0857 0.090 Uiso 1 1 calc R . .
H9B2 H 0.3500 0.5202 0.0757 0.090 Uiso 1 1 calc R . .
H9B3 H 0.3860 0.4969 0.0298 0.090 Uiso 1 1 calc R . .
C10B C 0.5015(4) 0.3631(7) 0.0955(4) 0.048(2) Uani 1 1 d . . .
C11B C 0.6142(5) 0.4575(9) 0.1040(5) 0.076(3) Uani 1 1 d . . .
H11D H 0.6381 0.5333 0.1119 0.114 Uiso 1 1 calc R . .
H11E H 0.6099 0.4310 0.0657 0.114 Uiso 1 1 calc R . .
H11F H 0.6420 0.4008 0.1327 0.114 Uiso 1 1 calc R . .
C12B C 0.4903(6) 0.3129(8) 0.0352(4) 0.065(3) Uani 1 1 d . . .
H12D H 0.4619 0.2416 0.0289 0.098 Uiso 1 1 calc R . .
H12E H 0.5365 0.2951 0.0330 0.098 Uiso 1 1 calc R . .
H12F H 0.4655 0.3705 0.0058 0.098 Uiso 1 1 calc R . .
C13B C 0.6530(4) 0.1594(8) 0.3932(4) 0.051(2) Uani 1 1 d . . .
C14B C 0.6890(5) 0.0472(9) 0.4251(4) 0.067(3) Uani 1 1 d . . .
H14D H 0.6573 -0.0194 0.4102 0.100 Uiso 1 1 calc R . .
H14E H 0.6991 0.0560 0.4661 0.100 Uiso 1 1 calc R . .
H14F H 0.7334 0.0340 0.4190 0.100 Uiso 1 1 calc R . .
C15B C 0.7666(5) 0.2603(11) 0.4092(6) 0.096(4) Uani 1 1 d . . .
H15D H 0.7908 0.3344 0.4231 0.145 Uiso 1 1 calc R . .
H15E H 0.7622 0.2478 0.3695 0.145 Uiso 1 1 calc R . .
H15F H 0.7941 0.1966 0.4332 0.145 Uiso 1 1 calc R . .
C16B C 0.5813(4) 0.1900(7) 0.4018(3) 0.0428(19) Uani 1 1 d . . .
C17B C 0.4752(5) 0.0831(11) 0.3987(5) 0.083(3) Uani 1 1 d . . .
H17D H 0.4530 0.0061 0.3897 0.124 Uiso 1 1 calc R . .
H17E H 0.4437 0.1414 0.3734 0.124 Uiso 1 1 calc R . .
H17F H 0.4837 0.1027 0.4386 0.124 Uiso 1 1 calc R . .
C18B C 0.5924(6) 0.2406(9) 0.4606(4) 0.068(3) Uani 1 1 d . . .
H18D H 0.6191 0.3136 0.4658 0.103 Uiso 1 1 calc R . .
H18E H 0.6191 0.1850 0.4903 0.103 Uiso 1 1 calc R . .
H18F H 0.5463 0.2558 0.4634 0.103 Uiso 1 1 calc R . .
O1B O 0.5262(3) 0.4628(4) 0.2793(2) 0.0525(15) Uani 1 1 d . . .
H1B1 H 0.5308 0.4785 0.3130 0.079 Uiso 1 1 calc R . .
O2B O 0.4422(3) 0.4179(4) 0.1626(2) 0.0426(13) Uani 1 1 d . . .
O3B O 0.5396(3) 0.2729(4) 0.1355(2) 0.0436(13) Uani 1 1 d . . .
O4B O 0.6670(3) 0.2088(5) 0.2304(3) 0.0564(16) Uani 1 1 d . . .
O5B O 0.6398(3) 0.1377(4) 0.3325(2) 0.0462(14) Uani 1 1 d . . .
O6B O 0.5412(3) 0.2790(5) 0.3608(2) 0.0443(13) Uani 1 1 d . . .
O7B O 0.3866(3) 0.2935(5) 0.0835(3) 0.0597(16) Uani 1 1 d . . .
O8B O 0.5434(3) 0.4686(5) 0.1064(3) 0.0554(16) Uani 1 1 d . . .
O9B O 0.6960(3) 0.2633(6) 0.4123(3) 0.0668(18) Uani 1 1 d . . .
O10B O 0.5423(3) 0.0817(5) 0.3902(2) 0.0531(15) Uani 1 1 d . . .
S1B S 0.6920(3) 0.1306(6) 0.1878(3) 0.063(3) Uani 0.470(13) 1 d P A 1
O11B O 0.7255(12) 0.203(3) 0.1574(13) 0.082(6) Uani 0.470(13) 1 d P A 1
O12B O 0.6439(11) 0.050(2) 0.1587(12) 0.108(10) Uani 0.470(13) 1 d P A 1
C19B C 0.766(3) 0.071(5) 0.2406(15) 0.13(2) Uani 0.470(13) 1 d P A 1
F1B F 0.8020(16) 0.000(3) 0.2226(11) 0.193(16) Uani 0.470(13) 1 d P A 1
F2B F 0.7383(17) -0.009(2) 0.2737(11) 0.140(9) Uani 0.470(13) 1 d P A 1
F3B F 0.7830(13) 0.107(3) 0.2803(17) 0.148(12) Uani 0.470(13) 1 d P A 1
S1B' S 0.7097(4) 0.0911(6) 0.2368(5) 0.095(4) Uani 0.530(13) 1 d P A 2
O11' O 0.8158(11) 0.144(4) 0.2794(15) 0.157(14) Uani 0.530(13) 1 d P A 2
O12' O 0.6748(10) -0.0129(14) 0.2395(10) 0.093(6) Uani 0.530(13) 1 d P A 2
C19' C 0.725(4) 0.107(8) 0.169(4) 0.22(4) Uani 0.530(13) 1 d P A 2
F1B' F 0.7644(18) 0.210(3) 0.1735(19) 0.201(18) Uani 0.530(13) 1 d P A 2
F2B' F 0.770(2) 0.004(3) 0.175(2) 0.24(2) Uani 0.530(13) 1 d P A 2
F3B' F 0.666(3) 0.095(5) 0.1320(19) 0.22(3) Uani 0.530(13) 1 d P A 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A O1A 1.418(9) . ?
C1A C2A 1.494(10) . ?
C1A C6A 1.518(10) . ?
C1A H1A 0.9800 . ?
C2A O2A 1.426(8) . ?
C2A C3A 1.509(9) . ?
C2A H2A 0.9800 . ?
C3A O3A 1.424(8) . ?
C3A C4A 1.523(10) . ?
C3A H3A 0.9800 . ?
C4A C5A 1.486(10) . ?
C4A O4A 1.488(8) . ?
C4A H4A 0.9800 . ?
C5A O5A 1.425(8) . ?
C5A C6A 1.516(10) . ?
C5A H5A 0.9800 . ?
C6A O6A 1.426(9) . ?
C6A H6A 0.9800 . ?
C7A O7A 1.422(9) . ?
C7A O2A 1.424(9) . ?
C7A C8A 1.522(11) . ?
C7A C10A 1.534(11) . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 0.9600 . ?
C9A O7A 1.426(10) . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 0.9600 . ?
C10A O8A 1.422(9) . ?
C10A O3A 1.445(9) . ?
C10A C11A 1.515(12) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A O8A 1.419(11) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A O5A 1.424(9) . ?
C13A O9A 1.425(9) . ?
C13A C15A 1.507(12) . ?
C13A C16A 1.552(11) . ?
C14A O9A 1.433(10) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A O6A 1.413(10) . ?
C16A O10A 1.426(9) . ?
C16A C17A 1.524(11) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C18A O10A 1.413(11) . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A F3A 1.293(13) . ?
C19A F1A 1.302(19) . ?
C19A F2A 1.312(17) . ?
C19A S1A 1.771(14) . ?
O1A H1A1 0.8200 . ?
O4A S1A 1.528(6) . ?
O11A S1A 1.370(10) . ?
O12A S1A 1.411(10) . ?
C1B O1B 1.410(9) . ?
C1B C2B 1.501(10) . ?
C1B C6B 1.547(10) . ?
C1B H1B 0.9800 . ?
C2B O2B 1.426(8) . ?
C2B C3B 1.516(9) . ?
C2B H2B 0.9800 . ?
C3B O3B 1.421(9) . ?
C3B C4B 1.489(10) . ?
C3B H3B 0.9800 . ?
C4B O4B 1.493(8) . ?
C4B C5B 1.522(11) . ?
C4B H4B 0.9800 . ?
C5B O5B 1.418(9) . ?
C5B C6B 1.518(10) . ?
C5B H5B 0.9800 . ?
C6B O6B 1.415(9) . ?
C6B H6B 0.9800 . ?
C7B O7B 1.411(9) . ?
C7B O2B 1.418(9) . ?
C7B C9B 1.498(11) . ?
C7B C10B 1.552(11) . ?
C8B O7B 1.417(11) . ?
C8B H8B1 0.9600 . ?
C8B H8B2 0.9600 . ?
C8B H8B3 0.9600 . ?
C9B H9B1 0.9600 . ?
C9B H9B2 0.9600 . ?
C9B H9B3 0.9600 . ?
C10B O8B 1.417(9) . ?
C10B O3B 1.422(9) . ?
C10B C12B 1.523(12) . ?
C11B O8B 1.438(11) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B O9B 1.422(10) . ?
C13B O5B 1.438(10) . ?
C13B C14B 1.519(12) . ?
C13B C16B 1.554(11) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15B O9B 1.434(11) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B O10B 1.416(9) . ?
C16B O6B 1.436(9) . ?
C16B C18B 1.493(12) . ?
C17B O10B 1.425(10) . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
O1B H1B1 0.8200 . ?
O4B S1B' 1.550(8) . ?
O4B S1B 1.584(8) . ?
S1B O12B 1.32(2) . ?
S1B O11B 1.43(3) . ?
S1B C19B 1.70(3) . ?
C19B F3B 1.00(4) . ?
C19B F1B 1.26(4) . ?
C19B F2B 1.45(6) . ?
F2B F3B 1.56(4) . ?
S1B' O12' 1.373(16) . ?
S1B' C19' 1.80(6) . ?
S1B' O11' 2.07(2) . ?
C19' F3B' 1.20(9) . ?
C19' F2B' 1.43(8) . ?
C19' F1B' 1.39(9) . ?

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
O1A C1A C2A 108.5(6) . . ?
O1A C1A C6A 111.5(6) . . ?
C2A C1A C6A 107.2(6) . . ?
O1A C1A H1A 109.8 . . ?
C2A C1A H1A 109.8 . . ?
C6A C1A H1A 109.8 . . ?
O2A C2A C1A 110.8(5) . . ?
O2A C2A C3A 107.1(6) . . ?
C1A C2A C3A 112.7(6) . . ?
O2A C2A H2A 108.7 . . ?
C1A C2A H2A 108.7 . . ?
C3A C2A H2A 108.7 . . ?
O3A C3A C2A 110.6(6) . . ?
O3A C3A C4A 107.7(6) . . ?
C2A C3A C4A 111.5(6) . . ?
O3A C3A H3A 109.0 . . ?
C2A C3A H3A 109.0 . . ?
C4A C3A H3A 109.0 . . ?
C5A C4A O4A 107.0(6) . . ?
C5A C4A C3A 108.9(6) . . ?
O4A C4A C3A 106.9(6) . . ?
C5A C4A H4A 111.3 . . ?
O4A C4A H4A 111.3 . . ?
C3A C4A H4A 111.3 . . ?
O5A C5A C4A 108.6(5) . . ?
O5A C5A C6A 110.0(6) . . ?
C4A C5A C6A 112.1(6) . . ?
O5A C5A H5A 108.7 . . ?
C4A C5A H5A 108.7 . . ?
C6A C5A H5A 108.7 . . ?
O6A C6A C5A 108.6(6) . . ?
O6A C6A C1A 109.2(6) . . ?
C5A C6A C1A 111.0(6) . . ?
O6A C6A H6A 109.3 . . ?
C5A C6A H6A 109.3 . . ?
C1A C6A H6A 109.3 . . ?
O7A C7A O2A 109.5(6) . . ?
O7A C7A C8A 111.7(6) . . ?
O2A C7A C8A 105.6(6) . . ?
O7A C7A C10A 105.1(6) . . ?
O2A C7A C10A 111.7(6) . . ?
C8A C7A C10A 113.3(7) . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
O7A C9A H9A1 109.5 . . ?
O7A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
O7A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
O8A C10A O3A 109.5(6) . . ?
O8A C10A C11A 112.5(7) . . ?
O3A C10A C11A 106.5(6) . . ?
O8A C10A C7A 105.1(6) . . ?
O3A C10A C7A 109.6(6) . . ?
C11A C10A C7A 113.6(7) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O8A C12A H12A 109.5 . . ?
O8A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O8A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O5A C13A O9A 111.1(6) . . ?
O5A C13A C15A 106.1(7) . . ?
O9A C13A C15A 111.8(7) . . ?
O5A C13A C16A 109.8(6) . . ?
O9A C13A C16A 104.1(6) . . ?
C15A C13A C16A 114.0(7) . . ?
O9A C14A H14A 109.5 . . ?
O9A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
O9A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O6A C16A O10A 110.1(6) . . ?
O6A C16A C17A 105.9(7) . . ?
O10A C16A C17A 112.0(7) . . ?
O6A C16A C13A 112.0(6) . . ?
O10A C16A C13A 103.9(6) . . ?
C17A C16A C13A 113.1(7) . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O10A C18A H18A 109.5 . . ?
O10A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
O10A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
F3A C19A F1A 111.3(15) . . ?
F3A C19A F2A 109.2(14) . . ?
F1A C19A F2A 103.2(14) . . ?
F3A C19A S1A 112.1(11) . . ?
F1A C19A S1A 111.3(11) . . ?
F2A C19A S1A 109.4(12) . . ?
C1A O1A H1A1 109.5 . . ?
C7A O2A C2A 113.3(5) . . ?
C3A O3A C10A 112.4(5) . . ?
C4A O4A S1A 125.2(5) . . ?
C13A O5A C5A 111.7(5) . . ?
C16A O6A C6A 114.2(6) . . ?
C7A O7A C9A 116.6(6) . . ?
C12A O8A C10A 115.8(7) . . ?
C13A O9A C14A 116.3(7) . . ?
C18A O10A C16A 116.3(7) . . ?
O11A S1A O12A 118.7(8) . . ?
O11A S1A O4A 112.2(5) . . ?
O12A S1A O4A 109.5(6) . . ?
O11A S1A C19A 109.2(9) . . ?
O12A S1A C19A 104.5(8) . . ?
O4A S1A C19A 100.9(5) . . ?
O1B C1B C2B 110.4(6) . . ?
O1B C1B C6B 110.9(6) . . ?
C2B C1B C6B 107.5(6) . . ?
O1B C1B H1B 109.4 . . ?
C2B C1B H1B 109.4 . . ?
C6B C1B H1B 109.4 . . ?
O2B C2B C1B 109.5(5) . . ?
O2B C2B C3B 108.6(6) . . ?
C1B C2B C3B 112.1(6) . . ?
O2B C2B H2B 108.9 . . ?
C1B C2B H2B 108.9 . . ?
C3B C2B H2B 108.9 . . ?
O3B C3B C4B 107.9(5) . . ?
O3B C3B C2B 109.4(6) . . ?
C4B C3B C2B 111.1(6) . . ?
O3B C3B H3B 109.5 . . ?
C4B C3B H3B 109.5 . . ?
C2B C3B H3B 109.5 . . ?
C3B C4B O4B 106.5(6) . . ?
C3B C4B C5B 109.8(6) . . ?
O4B C4B C5B 106.2(6) . . ?
C3B C4B H4B 111.3 . . ?
O4B C4B H4B 111.3 . . ?
C5B C4B H4B 111.3 . . ?
O5B C5B C6B 109.2(6) . . ?
O5B C5B C4B 110.1(6) . . ?
C6B C5B C4B 111.1(6) . . ?
O5B C5B H5B 108.8 . . ?
C6B C5B H5B 108.8 . . ?
C4B C5B H5B 108.8 . . ?
O6B C6B C5B 109.9(6) . . ?
O6B C6B C1B 108.9(6) . . ?
C5B C6B C1B 110.5(6) . . ?
O6B C6B H6B 109.2 . . ?
C5B C6B H6B 109.2 . . ?
C1B C6B H6B 109.2 . . ?
O7B C7B O2B 110.2(6) . . ?
O7B C7B C9B 113.3(7) . . ?
O2B C7B C9B 106.0(6) . . ?
O7B C7B C10B 103.6(6) . . ?
O2B C7B C10B 110.2(6) . . ?
C9B C7B C10B 113.6(7) . . ?
O7B C8B H8B1 109.5 . . ?
O7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
O7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C7B C9B H9B1 109.5 . . ?
C7B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C7B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
O8B C10B O3B 110.0(6) . . ?
O8B C10B C12B 111.1(7) . . ?
O3B C10B C12B 105.0(6) . . ?
O8B C10B C7B 106.2(6) . . ?
O3B C10B C7B 111.5(6) . . ?
C12B C10B C7B 113.1(7) . . ?
O8B C11B H11D 109.5 . . ?
O8B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
O8B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O9B C13B O5B 109.9(7) . . ?
O9B C13B C14B 113.6(6) . . ?
O5B C13B C14B 105.4(7) . . ?
O9B C13B C16B 104.0(7) . . ?
O5B C13B C16B 110.7(6) . . ?
C14B C13B C16B 113.3(7) . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O9B C15B H15D 109.5 . . ?
O9B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O9B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O10B C16B O6B 109.7(6) . . ?
O10B C16B C18B 113.4(7) . . ?
O6B C16B C18B 105.1(7) . . ?
O10B C16B C13B 104.1(6) . . ?
O6B C16B C13B 111.1(6) . . ?
C18B C16B C13B 113.6(7) . . ?
O10B C17B H17D 109.5 . . ?
O10B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
O10B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16B C18B H18D 109.5 . . ?
C16B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C16B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C1B O1B H1B1 109.5 . . ?
C7B O2B C2B 113.8(5) . . ?
C3B O3B C10B 111.8(5) . . ?
C4B O4B S1B' 119.5(5) . . ?
C4B O4B S1B 124.8(5) . . ?
S1B' O4B S1B 45.4(4) . . ?
C5B O5B C13B 112.6(6) . . ?
C6B O6B C16B 113.6(6) . . ?
C7B O7B C8B 116.1(7) . . ?
C10B O8B C11B 115.8(6) . . ?
C13B O9B C15B 116.4(7) . . ?
C16B O10B C17B 115.7(7) . . ?
O12B S1B O11B 119.7(18) . . ?
O12B S1B O4B 113.6(11) . . ?
O11B S1B O4B 110.4(12) . . ?
O12B S1B C19B 113(3) . . ?
O11B S1B C19B 101(2) . . ?
O4B S1B C19B 96.1(13) . . ?
F3B C19B F1B 125(4) . . ?
F3B C19B F2B 77(4) . . ?
F1B C19B F2B 101(4) . . ?
F3B C19B S1B 118(3) . . ?
F1B C19B S1B 115(3) . . ?
F2B C19B S1B 106(4) . . ?
C19B F2B F3B 39(2) . . ?
C19B F3B F2B 65(4) . . ?
O12' S1B' O4B 117.8(8) . . ?
O12' S1B' C19' 113(3) . . ?
O4B S1B' C19' 96(3) . . ?
O12' S1B' O11' 131.4(17) . . ?
O4B S1B' O11' 102.8(12) . . ?
C19' S1B' O11' 87(3) . . ?
F3B' C19' F2B' 113(8) . . ?
F3B' C19' F1B' 121(9) . . ?
F2B' C19' F1B' 111(5) . . ?
F3B' C19' S1B' 104(5) . . ?
F2B' C19' S1B' 98(5) . . ?
F1B' C19' S1B' 107(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
O1A C1A C2A O2A 57.3(7) . . . . ?
C6A C1A C2A O2A 177.9(5) . . . . ?
O1A C1A C2A C3A -62.7(7) . . . . ?
C6A C1A C2A C3A 57.9(7) . . . . ?
O2A C2A C3A O3A 60.6(7) . . . . ?
C1A C2A C3A O3A -177.3(6) . . . . ?
O2A C2A C3A C4A -179.6(6) . . . . ?
C1A C2A C3A C4A -57.5(8) . . . . ?
O3A C3A C4A C5A 175.6(5) . . . . ?
C2A C3A C4A C5A 54.0(8) . . . . ?
O3A C3A C4A O4A -69.2(7) . . . . ?
C2A C3A C4A O4A 169.3(6) . . . . ?
O4A C4A C5A O5A 67.5(7) . . . . ?
C3A C4A C5A O5A -177.3(5) . . . . ?
O4A C4A C5A C6A -170.8(5) . . . . ?
C3A C4A C5A C6A -55.6(8) . . . . ?
O5A C5A C6A O6A -59.3(7) . . . . ?
C4A C5A C6A O6A 179.7(6) . . . . ?
O5A C5A C6A C1A -179.5(6) . . . . ?
C4A C5A C6A C1A 59.6(8) . . . . ?
O1A C1A C6A O6A -59.2(7) . . . . ?
C2A C1A C6A O6A -177.9(5) . . . . ?
O1A C1A C6A C5A 60.6(8) . . . . ?
C2A C1A C6A C5A -58.1(7) . . . . ?
O7A C7A C10A O8A -173.6(6) . . . . ?
O2A C7A C10A O8A 67.8(7) . . . . ?
C8A C7A C10A O8A -51.3(8) . . . . ?
O7A C7A C10A O3A 68.9(7) . . . . ?
O2A C7A C10A O3A -49.8(8) . . . . ?
C8A C7A C10A O3A -168.9(6) . . . . ?
O7A C7A C10A C11A -50.1(8) . . . . ?
O2A C7A C10A C11A -168.7(6) . . . . ?
C8A C7A C10A C11A 72.1(9) . . . . ?
O5A C13A C16A O6A 49.8(8) . . . . ?
O9A C13A C16A O6A -69.1(7) . . . . ?
C15A C13A C16A O6A 168.7(7) . . . . ?
O5A C13A C16A O10A -68.9(7) . . . . ?
O9A C13A C16A O10A 172.1(6) . . . . ?
C15A C13A C16A O10A 50.0(9) . . . . ?
O5A C13A C16A C17A 169.4(6) . . . . ?
O9A C13A C16A C17A 50.4(8) . . . . ?
C15A C13A C16A C17A -71.7(9) . . . . ?
O7A C7A O2A C2A -60.5(7) . . . . ?
C8A C7A O2A C2A 179.2(6) . . . . ?
C10A C7A O2A C2A 55.6(7) . . . . ?
C1A C2A O2A C7A 177.4(6) . . . . ?
C3A C2A O2A C7A -59.4(7) . . . . ?
C2A C3A O3A C10A -59.9(7) . . . . ?
C4A C3A O3A C10A 178.0(6) . . . . ?
O8A C10A O3A C3A -61.8(7) . . . . ?
C11A C10A O3A C3A 176.3(6) . . . . ?
C7A C10A O3A C3A 53.0(7) . . . . ?
C5A C4A O4A S1A -138.4(6) . . . . ?
C3A C4A O4A S1A 105.0(6) . . . . ?
O9A C13A O5A C5A 59.1(7) . . . . ?
C15A C13A O5A C5A -179.2(6) . . . . ?
C16A C13A O5A C5A -55.5(8) . . . . ?
C4A C5A O5A C13A -175.3(6) . . . . ?
C6A C5A O5A C13A 61.6(7) . . . . ?
O10A C16A O6A C6A 63.2(8) . . . . ?
C17A C16A O6A C6A -175.5(6) . . . . ?
C13A C16A O6A C6A -51.8(8) . . . . ?
C5A C6A O6A C16A 55.8(7) . . . . ?
C1A C6A O6A C16A 177.0(6) . . . . ?
O2A C7A O7A C9A -54.8(8) . . . . ?
C8A C7A O7A C9A 61.8(9) . . . . ?
C10A C7A O7A C9A -174.9(7) . . . . ?
O3A C10A O8A C12A -59.2(9) . . . . ?
C11A C10A O8A C12A 59.0(10) . . . . ?
C7A C10A O8A C12A -176.8(7) . . . . ?
O5A C13A O9A C14A 55.3(9) . . . . ?
C15A C13A O9A C14A -63.0(10) . . . . ?
C16A C13A O9A C14A 173.4(7) . . . . ?
O6A C16A O10A C18A 61.2(9) . . . . ?
C17A C16A O10A C18A -56.4(10) . . . . ?
C13A C16A O10A C18A -178.7(7) . . . . ?
C4A O4A S1A O11A 6.3(10) . . . . ?
C4A O4A S1A O12A -127.8(8) . . . . ?
C4A O4A S1A C19A 122.4(9) . . . . ?
F3A C19A S1A O11A -64.0(15) . . . . ?
F1A C19A S1A O11A 170.7(12) . . . . ?
F2A C19A S1A O11A 57.3(14) . . . . ?
F3A C19A S1A O12A 64.0(16) . . . . ?
F1A C19A S1A O12A -61.3(13) . . . . ?
F2A C19A S1A O12A -174.7(13) . . . . ?
F3A C19A S1A O4A 177.7(13) . . . . ?
F1A C19A S1A O4A 52.4(13) . . . . ?
F2A C19A S1A O4A -61.0(14) . . . . ?
O1B C1B C2B O2B -57.8(7) . . . . ?
C6B C1B C2B O2B -178.9(5) . . . . ?
O1B C1B C2B C3B 62.7(7) . . . . ?
C6B C1B C2B C3B -58.3(7) . . . . ?
O2B C2B C3B O3B -60.5(7) . . . . ?
C1B C2B C3B O3B 178.4(6) . . . . ?
O2B C2B C3B C4B -179.6(6) . . . . ?
C1B C2B C3B C4B 59.4(8) . . . . ?
O3B C3B C4B O4B 69.3(7) . . . . ?
C2B C3B C4B O4B -170.8(6) . . . . ?
O3B C3B C4B C5B -176.1(6) . . . . ?
C2B C3B C4B C5B -56.2(8) . . . . ?
C3B C4B C5B O5B 177.8(6) . . . . ?
O4B C4B C5B O5B -67.4(7) . . . . ?
C3B C4B C5B C6B 56.6(8) . . . . ?
O4B C4B C5B C6B 171.4(6) . . . . ?
O5B C5B C6B O6B 60.0(8) . . . . ?
C4B C5B C6B O6B -178.3(6) . . . . ?
O5B C5B C6B C1B -179.7(6) . . . . ?
C4B C5B C6B C1B -58.1(8) . . . . ?
O1B C1B C6B O6B 57.9(7) . . . . ?
C2B C1B C6B O6B 178.6(6) . . . . ?
O1B C1B C6B C5B -62.9(8) . . . . ?
C2B C1B C6B C5B 57.8(8) . . . . ?
O7B C7B C10B O8B 171.9(6) . . . . ?
O2B C7B C10B O8B -70.2(8) . . . . ?
C9B C7B C10B O8B 48.6(9) . . . . ?
O7B C7B C10B O3B -68.3(8) . . . . ?
O2B C7B C10B O3B 49.6(8) . . . . ?
C9B C7B C10B O3B 168.4(7) . . . . ?
O7B C7B C10B C12B 49.8(8) . . . . ?
O2B C7B C10B C12B 167.7(6) . . . . ?
C9B C7B C10B C12B -73.5(9) . . . . ?
O9B C13B C16B O10B -172.6(6) . . . . ?
O5B C13B C16B O10B 69.5(8) . . . . ?
C14B C13B C16B O10B -48.7(9) . . . . ?
O9B C13B C16B O6B 69.5(8) . . . . ?
O5B C13B C16B O6B -48.5(8) . . . . ?
C14B C13B C16B O6B -166.6(7) . . . . ?
O9B C13B C16B C18B -48.7(9) . . . . ?
O5B C13B C16B C18B -166.7(7) . . . . ?
C14B C13B C16B C18B 75.2(10) . . . . ?
O7B C7B O2B C2B 60.8(7) . . . . ?
C9B C7B O2B C2B -176.3(6) . . . . ?
C10B C7B O2B C2B -53.0(8) . . . . ?
C1B C2B O2B C7B -178.7(6) . . . . ?
C3B C2B O2B C7B 58.7(7) . . . . ?
C4B C3B O3B C10B -178.7(6) . . . . ?
C2B C3B O3B C10B 60.3(7) . . . . ?
O8B C10B O3B C3B 62.8(8) . . . . ?
C12B C10B O3B C3B -177.6(6) . . . . ?
C7B C10B O3B C3B -54.7(8) . . . . ?
C3B C4B O4B S1B' -148.4(7) . . . . ?
C5B C4B O4B S1B' 94.5(8) . . . . ?
C3B C4B O4B S1B -94.5(7) . . . . ?
C5B C4B O4B S1B 148.4(6) . . . . ?
C6B C5B O5B C13B -59.9(8) . . . . ?
C4B C5B O5B C13B 177.8(6) . . . . ?
O9B C13B O5B C5B -60.0(7) . . . . ?
C14B C13B O5B C5B 177.2(6) . . . . ?
C16B C13B O5B C5B 54.3(8) . . . . ?
C5B C6B O6B C16B -57.3(8) . . . . ?
C1B C6B O6B C16B -178.6(6) . . . . ?
O10B C16B O6B C6B -62.8(8) . . . . ?
C18B C16B O6B C6B 175.0(6) . . . . ?
C13B C16B O6B C6B 51.7(8) . . . . ?
O2B C7B O7B C8B 56.7(9) . . . . ?
C9B C7B O7B C8B -61.9(10) . . . . ?
C10B C7B O7B C8B 174.6(8) . . . . ?
O3B C10B O8B C11B 57.0(9) . . . . ?
C12B C10B O8B C11B -58.8(10) . . . . ?
C7B C10B O8B C11B 177.8(7) . . . . ?
O5B C13B O9B C15B -61.5(10) . . . . ?
C14B C13B O9B C15B 56.3(11) . . . . ?
C16B C13B O9B C15B 180.0(8) . . . . ?
O6B C16B O10B C17B -65.0(9) . . . . ?
C18B C16B O10B C17B 52.1(10) . . . . ?
C13B C16B O10B C17B 176.1(7) . . . . ?
C4B O4B S1B O12B -8.5(18) . . . . ?
S1B' O4B S1B O12B 90.6(17) . . . . ?
C4B O4B S1B O11B 129.2(13) . . . . ?
S1B' O4B S1B O11B -131.7(12) . . . . ?
C4B O4B S1B C19B -127(2) . . . . ?
S1B' O4B S1B C19B -28(2) . . . . ?
O12B S1B C19B F3B -133(7) . . . . ?
O11B S1B C19B F3B 98(7) . . . . ?
O4B S1B C19B F3B -14(7) . . . . ?
O12B S1B C19B F1B 62(6) . . . . ?
O11B S1B C19B F1B -67(5) . . . . ?
O4B S1B C19B F1B -180(5) . . . . ?
O12B S1B C19B F2B -49(3) . . . . ?
O11B S1B C19B F2B -178(3) . . . . ?
O4B S1B C19B F2B 70(3) . . . . ?
F1B C19B F2B F3B 123(5) . . . . ?
S1B C19B F2B F3B -116(3) . . . . ?
F1B C19B F3B F2B -94(7) . . . . ?
S1B C19B F3B F2B 101(5) . . . . ?
C4B O4B S1B' O12' 5.4(16) . . . . ?
S1B O4B S1B' O12' -105.9(15) . . . . ?
C4B O4B S1B' C19' 125(3) . . . . ?
S1B O4B S1B' C19' 13(3) . . . . ?
C4B O4B S1B' O11' -147.0(12) . . . . ?
S1B O4B S1B' O11' 101.7(12) . . . . ?
O12' S1B' C19' F3B' 54(7) . . . . ?
O4B S1B' C19' F3B' -69(7) . . . . ?
O11' S1B' C19' F3B' -171(7) . . . . ?
O12' S1B' C19' F2B' -62(5) . . . . ?
O4B S1B' C19' F2B' 175(4) . . . . ?
O11' S1B' C19' F2B' 73(4) . . . . ?
O12' S1B' C19' F1B' -176(4) . . . . ?
O4B S1B' C19' F1B' 61(5) . . . . ?
O11' S1B' C19' F1B' -42(5) . . . . ?

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
C5A H5A F3A 0.98 2.59 3.512(9) 157.2 2
C6A H6A O1B 0.98 2.47 3.338(9) 147.9 .
C8A H8A3 O12B 0.96 2.63 3.52(2) 153.1 1_565
C18A H18A F2B' 0.96 2.60 3.12(3) 113.6 2_655
C18A H18C F1B' 0.96 2.50 3.36(3) 149.6 2_655
O1A H1A1 O10B 0.82 2.11 2.879(8) 156.1 1_565
C6B H6B O1A 0.98 2.43 3.321(9) 150.5 1_545
O1B H1B1 O10A 0.82 2.14 2.898(8) 153.8 .
C5A H5A F3A 0.98 2.59 3.512(9) 157.2 2
C6A H6A O1B 0.98 2.47 3.338(9) 147.9 .
C8A H8A3 O12B 0.96 2.63 3.52(2) 153.1 1_565
C18A H18A F2B' 0.96 2.60 3.12(3) 113.6 2_655
C18A H18C F1B' 0.96 2.50 3.36(3) 149.6 2_655
O1A H1A1 O10B 0.82 2.11 2.879(8) 156.1 1_565
C6B H6B O1A 0.98 2.43 3.321(9) 150.5 1_545
O1B H1B1 O10A 0.82 2.14 2.898(8) 153.8 .

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.226
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532602'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H31 N3 O9'
_chemical_formula_sum            'C18 H31 N3 O9'
_chemical_formula_weight         433.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.8946(3)
_cell_length_b                   17.0004(5)
_cell_length_c                   21.7463(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4397.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3805
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      24.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.308
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            20401
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4323
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.8675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4323
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_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
C1 C 0.49754(16) 0.80274(12) 0.65284(11) 0.0424(6) Uani 1 1 d . . . . .
H1 H 0.5448 0.8168 0.6881 0.051 Uiso 1 1 calc R U . . .
C2 C 0.39035(16) 0.85062(13) 0.65355(11) 0.0440(6) Uani 1 1 d . . . . .
H2 H 0.3413 0.8332 0.6200 0.053 Uiso 1 1 calc R U . . .
C3 C 0.41537(17) 0.93686(13) 0.64611(12) 0.0465(6) Uani 1 1 d . . . . .
H3 H 0.4622 0.9544 0.6806 0.056 Uiso 1 1 calc R U . . .
C4 C 0.47566(17) 0.95526(13) 0.58604(12) 0.0446(6) Uani 1 1 d . U . . .
H4 H 0.4945 1.0113 0.5844 0.054 Uiso 1 1 calc R U . . .
C5 C 0.58268(16) 0.90659(12) 0.58607(11) 0.0410(6) Uani 1 1 d . . . . .
H5 H 0.6307 0.9241 0.6200 0.049 Uiso 1 1 calc R U . . .
C6 C 0.55877(16) 0.81991(12) 0.59367(11) 0.0392(6) Uani 1 1 d . . . . .
H6 H 0.5135 0.8015 0.5589 0.047 Uiso 1 1 calc R U . . .
C7 C 0.22916(17) 0.87895(15) 0.71470(12) 0.0538(7) Uani 1 1 d . . . . .
C8 C 0.2478(2) 0.96753(15) 0.70158(13) 0.0586(7) Uani 1 1 d . . . . .
C9 C 0.74498(18) 0.87434(14) 0.52469(12) 0.0501(7) Uani 1 1 d . . . . .
C10 C 0.72555(18) 0.78604(14) 0.53974(12) 0.0502(6) Uani 1 1 d . . . . .
C11 C 0.1319(2) 0.77029(18) 0.66781(15) 0.0823(9) Uani 1 1 d . . . . .
H11A H 0.2001 0.7409 0.6733 0.124 Uiso 1 1 calc R U . . .
H11B H 0.0974 0.7557 0.6296 0.124 Uiso 1 1 calc R U . . .
H11C H 0.0813 0.7592 0.7011 0.124 Uiso 1 1 calc R U . . .
C12 C 0.1829(2) 0.86180(18) 0.77776(13) 0.0689(8) Uani 1 1 d . . . . .
H12A H 0.1065 0.8796 0.7801 0.103 Uiso 1 1 calc R U . . .
H12B H 0.2272 0.8886 0.8081 0.103 Uiso 1 1 calc R U . . .
H12C H 0.1856 0.8062 0.7853 0.103 Uiso 1 1 calc R U . . .
C13 C 0.1382(2) 1.01147(17) 0.69100(16) 0.0799(10) Uani 1 1 d . . . . .
H13A H 0.0932 1.0093 0.7276 0.120 Uiso 1 1 calc R U . . .
H13B H 0.0980 0.9875 0.6576 0.120 Uiso 1 1 calc R U . . .
H13C H 0.1542 1.0654 0.6811 0.120 Uiso 1 1 calc R U . . .
C14 C 0.3404(3) 1.0748(2) 0.75261(19) 0.1110(14) Uani 1 1 d . . . . .
H14A H 0.3822 1.0853 0.7157 0.167 Uiso 1 1 calc R U . . .
H14B H 0.3864 1.0862 0.7878 0.167 Uiso 1 1 calc R U . . .
H14C H 0.2744 1.1073 0.7535 0.167 Uiso 1 1 calc R U . . .
C15 C 0.8499(3) 0.98035(18) 0.57058(18) 0.0946(11) Uani 1 1 d . . . . .
H15A H 0.8983 0.9908 0.5362 0.142 Uiso 1 1 calc R U . . .
H15B H 0.8885 0.9929 0.6081 0.142 Uiso 1 1 calc R U . . .
H15C H 0.7833 1.0119 0.5673 0.142 Uiso 1 1 calc R U . . .
C16 C 0.7867(2) 0.88823(17) 0.46011(14) 0.0724(9) Uani 1 1 d . . . . .
H16A H 0.7971 0.9436 0.4536 0.109 Uiso 1 1 calc R U . . .
H16B H 0.7327 0.8684 0.4312 0.109 Uiso 1 1 calc R U . . .
H16C H 0.8571 0.8615 0.4544 0.109 Uiso 1 1 calc R U . . .
C17 C 0.83485(19) 0.74160(17) 0.55158(15) 0.0723(9) Uani 1 1 d . . . . .
H17A H 0.8180 0.6885 0.5635 0.109 Uiso 1 1 calc R U . . .
H17B H 0.8759 0.7671 0.5839 0.109 Uiso 1 1 calc R U . . .
H17C H 0.8794 0.7412 0.5148 0.109 Uiso 1 1 calc R U . . .
C18 C 0.6355(2) 0.67452(15) 0.49294(15) 0.0768(9) Uani 1 1 d . . . . .
H18A H 0.7004 0.6433 0.4834 0.115 Uiso 1 1 calc R U . . .
H18B H 0.5767 0.6632 0.4640 0.115 Uiso 1 1 calc R U . . .
H18C H 0.6101 0.6624 0.5337 0.115 Uiso 1 1 calc R U . . .
N1 N 0.46451(16) 0.71827(12) 0.65645(11) 0.0599(6) Uani 1 1 d . . . . .
N2 N 0.5360(2) 0.67456(13) 0.66935(11) 0.0682(7) Uani 1 1 d . . . . .
N3 N 0.5981(2) 0.62411(17) 0.68012(18) 0.1214(13) Uani 1 1 d . . . . .
O2 O 0.33459(11) 0.83850(9) 0.71107(8) 0.0514(5) Uani 1 1 d . . . . .
O3 O 0.31172(12) 0.97918(9) 0.64704(9) 0.0591(5) Uani 1 1 d . . . . .
O4 O 0.40863(14) 0.93491(10) 0.53466(8) 0.0596(5) Uani 1 1 d . U . . .
H4A H 0.3887 0.9750 0.5168 0.089 Uiso 1 1 calc R U . . .
O5 O 0.64167(11) 0.91787(9) 0.52917(7) 0.0479(4) Uani 1 1 d . . . . .
O6 O 0.66275(11) 0.77798(8) 0.59494(7) 0.0447(4) Uani 1 1 d . . . . .
O7 O 0.15702(12) 0.85205(11) 0.66706(8) 0.0606(5) Uani 1 1 d . . . . .
O8 O 0.30826(14) 0.99457(12) 0.75375(10) 0.0743(6) Uani 1 1 d . . . . .
O9 O 0.82001(13) 0.90016(10) 0.57079(9) 0.0629(5) Uani 1 1 d . . . . .
O10 O 0.66418(14) 0.75598(10) 0.48943(8) 0.0619(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.491(3) . ?
C1 C6 1.507(3) . ?
C1 C2 1.513(3) . ?
C1 H1 0.9800 . ?
C2 O2 1.431(3) . ?
C2 C3 1.505(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.428(2) . ?
C3 C4 1.523(3) . ?
C3 H3 0.9800 . ?
C4 O4 1.416(3) . ?
C4 C5 1.518(3) . ?
C4 H4 0.9800 . ?
C5 O5 1.435(3) . ?
C5 C6 1.510(3) . ?
C5 H5 0.9800 . ?
C6 O6 1.428(2) . ?
C6 H6 0.9800 . ?
C7 O7 1.421(3) . ?
C7 O2 1.432(2) . ?
C7 C12 1.506(4) . ?
C7 C8 1.549(3) . ?
C8 O8 1.420(3) . ?
C8 O3 1.423(3) . ?
C8 C13 1.520(3) . ?
C9 O9 1.412(3) . ?
C9 O5 1.438(3) . ?
C9 C16 1.508(4) . ?
C9 C10 1.554(3) . ?
C10 O10 1.411(3) . ?
C10 O6 1.420(3) . ?
C10 C17 1.525(3) . ?
C11 O7 1.422(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O8 1.417(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O9 1.409(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O10 1.428(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.163(3) . ?
N2 N3 1.156(3) . ?
O4 H4A 0.8200 . ?

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
N1 C1 C6 111.04(18) . . ?
N1 C1 C2 107.20(16) . . ?
C6 C1 C2 108.17(17) . . ?
N1 C1 H1 110.1 . . ?
C6 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
O2 C2 C3 109.03(18) . . ?
O2 C2 C1 108.80(17) . . ?
C3 C2 C1 110.88(17) . . ?
O2 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
O3 C3 C2 108.58(17) . . ?
O3 C3 C4 108.38(18) . . ?
C2 C3 C4 112.68(19) . . ?
O3 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
O4 C4 C5 109.84(18) . . ?
O4 C4 C3 111.21(18) . . ?
C5 C4 C3 106.41(18) . . ?
O4 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
O5 C5 C6 108.47(17) . . ?
O5 C5 C4 109.68(17) . . ?
C6 C5 C4 111.96(17) . . ?
O5 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
O6 C6 C1 107.79(16) . . ?
O6 C6 C5 109.04(15) . . ?
C1 C6 C5 111.94(18) . . ?
O6 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
O7 C7 O2 109.51(19) . . ?
O7 C7 C12 112.40(19) . . ?
O2 C7 C12 106.09(19) . . ?
O7 C7 C8 105.4(2) . . ?
O2 C7 C8 109.36(18) . . ?
C12 C7 C8 114.1(2) . . ?
O8 C8 O3 110.49(19) . . ?
O8 C8 C13 113.4(2) . . ?
O3 C8 C13 105.3(2) . . ?
O8 C8 C7 103.9(2) . . ?
O3 C8 C7 111.4(2) . . ?
C13 C8 C7 112.5(2) . . ?
O9 C9 O5 109.40(18) . . ?
O9 C9 C16 113.8(2) . . ?
O5 C9 C16 105.30(19) . . ?
O9 C9 C10 104.17(19) . . ?
O5 C9 C10 110.84(17) . . ?
C16 C9 C10 113.4(2) . . ?
O10 C10 O6 110.38(18) . . ?
O10 C10 C17 113.1(2) . . ?
O6 C10 C17 104.9(2) . . ?
O10 C10 C9 105.3(2) . . ?
O6 C10 C9 110.45(18) . . ?
C17 C10 C9 112.8(2) . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 N1 C1 115.80(19) . . ?
N3 N2 N1 171.8(3) . . ?
C2 O2 C7 112.64(16) . . ?
C8 O3 C3 113.78(17) . . ?
C4 O4 H4A 109.5 . . ?
C5 O5 C9 114.05(16) . . ?
C10 O6 C6 113.03(16) . . ?
C7 O7 C11 115.7(2) . . ?
C14 O8 C8 115.8(3) . . ?
C15 O9 C9 117.3(2) . . ?
C10 O10 C18 115.7(2) . . ?

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
C1 H1 O2 0.98 2.65 3.622(3) 173.3 3_656
C14 H14C N3 0.96 2.56 3.339(4) 138.2 8_567
O4 H4A O5 0.82 2.11 2.924(2) 173.0 5_676

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532606'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H34 O12 S'
_chemical_formula_sum            'C19 H34 O12 S'
_chemical_formula_weight         486.52
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.0560(4)
_cell_length_b                   12.5770(4)
_cell_length_c                   17.1284(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.265(2)
_cell_angle_gamma                90
_cell_volume                     2381.15(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6132
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.358
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            19788
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.009
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4682
_reflns_number_gt                3281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4682
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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_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
C1 C 0.12049(15) 0.07121(13) 0.43531(9) 0.0309(4) Uani 1 1 d . . . . .
H1 H 0.1066 0.1012 0.4872 0.037 Uiso 1 1 calc R U . . .
C2 C 0.21693(15) -0.01445(12) 0.44117(9) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.2907 0.0166 0.4643 0.036 Uiso 1 1 calc R U . . .
C3 C 0.24664(15) -0.06147(13) 0.36216(8) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.1752 -0.0971 0.3396 0.034 Uiso 1 1 calc R U . . .
C4 C 0.28979(15) 0.02339(13) 0.30713(8) 0.0294(4) Uani 1 1 d . . . . .
H4 H 0.3690 0.0501 0.3248 0.035 Uiso 1 1 calc R U . . .
C5 C 0.20001(15) 0.11332(13) 0.30227(9) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.1253 0.0879 0.2767 0.037 Uiso 1 1 calc R U . . .
C6 C 0.17097(15) 0.15656(13) 0.38218(9) 0.0319(4) Uani 1 1 d . . . . .
H6 H 0.2450 0.1857 0.4064 0.038 Uiso 1 1 calc R U . . .
C7 C 0.26539(16) -0.18122(14) 0.50227(9) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.31222(16) -0.22326(13) 0.42292(9) 0.0334(4) Uani 1 1 d . . . . .
C9 C 0.16597(17) 0.28259(14) 0.24519(10) 0.0399(4) Uani 1 1 d . . . . .
C10 C 0.12405(18) 0.32500(14) 0.32532(11) 0.0413(4) Uani 1 1 d . . . . .
C11 C 0.2017(2) -0.26536(16) 0.54921(11) 0.0526(6) Uani 1 1 d . . . . .
H11A H 0.2543 -0.3255 0.5565 0.079 Uiso 1 1 calc R U . . .
H11B H 0.1293 -0.2873 0.5218 0.079 Uiso 1 1 calc R U . . .
H11C H 0.1812 -0.2367 0.5992 0.079 Uiso 1 1 calc R U . . .
C12 C 0.3514(2) -0.07993(19) 0.60908(11) 0.0710(7) Uani 1 1 d . . . . .
H12A H 0.4279 -0.0555 0.6297 0.106 Uiso 1 1 calc R U . . .
H12B H 0.3006 -0.0199 0.5972 0.106 Uiso 1 1 calc R U . . .
H12C H 0.3131 -0.1241 0.6470 0.106 Uiso 1 1 calc R U . . .
C13 C 0.42628(18) -0.28892(15) 0.43216(11) 0.0481(5) Uani 1 1 d . . . . .
H13A H 0.4099 -0.3508 0.4630 0.072 Uiso 1 1 calc R U . . .
H13B H 0.4881 -0.2472 0.4577 0.072 Uiso 1 1 calc R U . . .
H13C H 0.4532 -0.3104 0.3816 0.072 Uiso 1 1 calc R U . . .
C14 C 0.23142(19) -0.32273(16) 0.31375(11) 0.0503(5) Uani 1 1 d . . . . .
H14A H 0.2606 -0.2676 0.2802 0.076 Uiso 1 1 calc R U . . .
H14B H 0.1560 -0.3495 0.2931 0.076 Uiso 1 1 calc R U . . .
H14C H 0.2895 -0.3794 0.3166 0.076 Uiso 1 1 calc R U . . .
C15 C 0.23063(19) 0.36610(16) 0.19771(12) 0.0561(6) Uani 1 1 d . . . . .
H15A H 0.2716 0.3324 0.1555 0.084 Uiso 1 1 calc R U . . .
H15B H 0.2885 0.4027 0.2306 0.084 Uiso 1 1 calc R U . . .
H15C H 0.1727 0.4161 0.1770 0.084 Uiso 1 1 calc R U . . .
C16 C 0.0780(2) 0.20152(19) 0.13070(11) 0.0641(6) Uani 1 1 d . . . . .
H16A H 0.0947 0.2581 0.0949 0.096 Uiso 1 1 calc R U . . .
H16B H 0.0062 0.1645 0.1135 0.096 Uiso 1 1 calc R U . . .
H16C H 0.1449 0.1529 0.1325 0.096 Uiso 1 1 calc R U . . .
C17 C 0.0173(2) 0.40030(16) 0.31771(14) 0.0601(6) Uani 1 1 d . . . . .
H17A H -0.0075 0.4216 0.3687 0.090 Uiso 1 1 calc R U . . .
H17B H -0.0486 0.3650 0.2910 0.090 Uiso 1 1 calc R U . . .
H17C H 0.0404 0.4619 0.2885 0.090 Uiso 1 1 calc R U . . .
C18 C 0.2182(3) 0.4156(2) 0.43524(13) 0.0792(8) Uani 1 1 d . . . . .
H18A H 0.1760 0.4823 0.4323 0.119 Uiso 1 1 calc R U . . .
H18B H 0.2973 0.4265 0.4580 0.119 Uiso 1 1 calc R U . . .
H18C H 0.1739 0.3669 0.4670 0.119 Uiso 1 1 calc R U . . .
C19 C 0.4704(2) -0.15555(17) 0.19504(14) 0.0642(6) Uani 1 1 d . . . . .
H19A H 0.4134 -0.2024 0.1697 0.096 Uiso 1 1 calc R U . . .
H19B H 0.4766 -0.1728 0.2496 0.096 Uiso 1 1 calc R U . . .
H19C H 0.5482 -0.1636 0.1719 0.096 Uiso 1 1 calc R U . . .
O1 O 0.01089(10) 0.02798(9) 0.40427(7) 0.0366(3) Uani 1 1 d . . . . .
H1A H -0.0467 0.0555 0.4259 0.055 Uiso 1 1 calc R U . . .
O2 O 0.17714(10) -0.09860(9) 0.49036(6) 0.0337(3) Uani 1 1 d . . . . .
O3 O 0.34276(10) -0.13643(9) 0.37309(6) 0.0327(3) Uani 1 1 d . . . . .
O4 O 0.29856(10) -0.02370(9) 0.22953(6) 0.0344(3) Uani 1 1 d . . . . .
O5 O 0.24990(11) 0.19715(9) 0.25658(6) 0.0366(3) Uani 1 1 d . . . . .
O6 O 0.08404(11) 0.23980(9) 0.37338(7) 0.0385(3) Uani 1 1 d . . . . .
O7 O 0.36985(12) -0.13950(11) 0.53996(7) 0.0510(4) Uani 1 1 d . . . . .
O8 O 0.21388(11) -0.28059(9) 0.39000(6) 0.0390(3) Uani 1 1 d . . . . .
O9 O 0.06025(12) 0.24442(11) 0.20641(7) 0.0473(3) Uani 1 1 d . . . . .
O10 O 0.22887(13) 0.37265(10) 0.35877(8) 0.0522(4) Uani 1 1 d . . . . .
O11 O 0.50551(12) 0.04459(11) 0.22259(7) 0.0531(4) Uani 1 1 d . . . . .
O12 O 0.38821(14) -0.00625(13) 0.10488(7) 0.0635(4) Uani 1 1 d . . . . .
S1 S 0.42155(4) -0.02428(4) 0.18407(2) 0.04005(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.421(2) . ?
C1 C2 1.517(2) . ?
C1 C6 1.521(2) . ?
C1 H1 0.9800 . ?
C2 O2 1.4282(19) . ?
C2 C3 1.519(2) . ?
C2 H2 0.9800 . ?
C3 O3 1.4299(19) . ?
C3 C4 1.508(2) . ?
C3 H3 0.9800 . ?
C4 O4 1.4604(18) . ?
C4 C5 1.506(2) . ?
C4 H4 0.9800 . ?
C5 O5 1.4309(19) . ?
C5 C6 1.514(2) . ?
C5 H5 0.9800 . ?
C6 O6 1.4269(19) . ?
C6 H6 0.9800 . ?
C7 O7 1.412(2) . ?
C7 O2 1.4369(19) . ?
C7 C11 1.512(3) . ?
C7 C8 1.558(2) . ?
C8 O8 1.412(2) . ?
C8 O3 1.431(2) . ?
C8 C13 1.513(2) . ?
C9 O9 1.415(2) . ?
C9 O5 1.430(2) . ?
C9 C15 1.517(2) . ?
C9 C10 1.553(3) . ?
C10 O10 1.415(2) . ?
C10 O6 1.428(2) . ?
C10 C17 1.517(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O7 1.420(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O8 1.427(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O9 1.422(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O10 1.424(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 S1 1.746(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1 H1A 0.8200 . ?
O4 S1 1.5819(12) . ?
O11 S1 1.4214(13) . ?
O12 S1 1.4160(14) . ?

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 C1 C2 110.20(13) . . ?
O1 C1 C6 111.55(13) . . ?
C2 C1 C6 105.91(13) . . ?
O1 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C6 C1 H1 109.7 . . ?
O2 C2 C1 109.88(13) . . ?
O2 C2 C3 108.20(13) . . ?
C1 C2 C3 112.50(12) . . ?
O2 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
O3 C3 C4 107.70(12) . . ?
O3 C3 C2 108.34(12) . . ?
C4 C3 C2 111.03(13) . . ?
O3 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O4 C4 C5 108.13(12) . . ?
O4 C4 C3 108.07(12) . . ?
C5 C4 C3 110.41(13) . . ?
O4 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
O5 C5 C4 108.79(13) . . ?
O5 C5 C6 108.77(13) . . ?
C4 C5 C6 111.87(13) . . ?
O5 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
O6 C6 C5 108.90(12) . . ?
O6 C6 C1 109.01(13) . . ?
C5 C6 C1 112.04(14) . . ?
O6 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C1 C6 H6 108.9 . . ?
O7 C7 O2 110.02(14) . . ?
O7 C7 C11 113.74(14) . . ?
O2 C7 C11 105.02(14) . . ?
O7 C7 C8 103.93(14) . . ?
O2 C7 C8 111.06(12) . . ?
C11 C7 C8 113.20(15) . . ?
O8 C8 O3 109.95(12) . . ?
O8 C8 C13 113.32(14) . . ?
O3 C8 C13 105.77(14) . . ?
O8 C8 C7 104.71(14) . . ?
O3 C8 C7 110.41(13) . . ?
C13 C8 C7 112.74(13) . . ?
O9 C9 O5 109.62(14) . . ?
O9 C9 C15 112.17(15) . . ?
O5 C9 C15 106.34(15) . . ?
O9 C9 C10 105.77(15) . . ?
O5 C9 C10 110.05(13) . . ?
C15 C9 C10 112.91(16) . . ?
O10 C10 O6 110.24(14) . . ?
O10 C10 C17 113.54(16) . . ?
O6 C10 C17 105.53(15) . . ?
O10 C10 C9 104.23(15) . . ?
O6 C10 C9 110.75(15) . . ?
C17 C10 C9 112.67(15) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O7 C12 H12A 109.5 . . ?
O7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O9 C16 H16A 109.5 . . ?
O9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 O1 H1A 109.5 . . ?
C2 O2 C7 113.75(12) . . ?
C3 O3 C8 113.38(12) . . ?
C4 O4 S1 121.67(10) . . ?
C9 O5 C5 111.80(12) . . ?
C6 O6 C10 113.27(13) . . ?
C7 O7 C12 116.50(16) . . ?
C8 O8 C14 115.87(14) . . ?
C9 O9 C16 115.33(15) . . ?
C10 O10 C18 116.69(17) . . ?
O12 S1 O11 120.05(9) . . ?
O12 S1 O4 105.21(8) . . ?
O11 S1 O4 109.16(7) . . ?
O12 S1 C19 109.14(10) . . ?
O11 S1 C19 109.20(10) . . ?
O4 S1 C19 102.64(9) . . ?

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
C4 H4 O11 0.98 2.34 2.8300(19) 110.3 .
C12 H12A O11 0.96 2.62 3.288(2) 126.7 3_656
C13 H13C O11 0.96 2.60 3.474(2) 151.5 2_645
C14 H14C O11 0.96 2.56 3.422(2) 149.1 2_645
C16 H16B O8 0.96 2.53 3.246(3) 131.6 2
C19 H19B O3 0.96 2.65 3.397(2) 135.2 .
C19 H19C O10 0.96 2.57 3.488(3) 159.4 2_645
O1 H1A O2 0.82 2.13 2.9213(15) 163.1 3_556

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.068

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532608'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H31 F3 O12 S, C H Cl3'
_chemical_formula_sum            'C20 H32 Cl3 F3 O12 S'
_chemical_formula_weight         659.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.401(2)
_cell_length_b                   22.024(5)
_cell_length_c                   11.813(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2966.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1729
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      18.23

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.478
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            12661
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             5066
_reflns_number_gt                2606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.748
_reflns_Friedel_fraction_full    0.776

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1177P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.58(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5066
_refine_ls_number_parameters     353
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2287
_refine_ls_wR_factor_gt          0.1873
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_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_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
C1 C -0.0242(7) 0.3050(4) 0.2607(7) 0.042(2) Uani 1 1 d D . . . .
H1 H -0.0944 0.2968 0.3061 0.051 Uiso 1 1 calc R U . . .
C2 C -0.0305(7) 0.2697(3) 0.1510(7) 0.036(2) Uani 1 1 d D . . . .
H2 H 0.0387 0.2793 0.1051 0.043 Uiso 1 1 calc R U . . .
C3 C -0.0344(7) 0.2021(4) 0.1717(7) 0.038(2) Uani 1 1 d D . . . .
H3 H -0.1048 0.1922 0.2156 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0727(7) 0.1815(4) 0.2362(6) 0.037(2) Uani 1 1 d D . . . .
H4 H 0.1445 0.1864 0.1914 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0776(8) 0.2174(4) 0.3450(7) 0.041(2) Uani 1 1 d D . . . .
H5 H 0.0094 0.2077 0.3922 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0837(7) 0.2848(4) 0.3249(8) 0.041(2) Uani 1 1 d D . . . .
H6 H 0.1549 0.2952 0.2826 0.049 Uiso 1 1 calc R U . . .
C7 C -0.1417(8) 0.2567(4) -0.0175(8) 0.049(3) Uani 1 1 d D . . . .
C8 C -0.1356(8) 0.1882(4) -0.0028(7) 0.047(3) Uani 1 1 d D . . . .
C9 C 0.1936(8) 0.2288(4) 0.5114(8) 0.049(3) Uani 1 1 d D . . . .
C10 C 0.1834(8) 0.2972(4) 0.5013(7) 0.052(3) Uani 1 1 d D . . . .
C11 C -0.2557(8) 0.2795(6) -0.0701(9) 0.063(3) Uani 1 1 d D . . . .
H11A H -0.3204 0.2689 -0.0219 0.094 Uiso 1 1 calc R U . . .
H11B H -0.2522 0.3228 -0.0785 0.094 Uiso 1 1 calc R U . . .
H11C H -0.2663 0.2610 -0.1430 0.094 Uiso 1 1 calc R U . . .
C12 C -0.0212(11) 0.3324(7) -0.1066(10) 0.074(4) Uani 1 1 d . . . . .
H12A H 0.0488 0.3361 -0.1513 0.110 Uiso 1 1 calc R U . . .
H12B H -0.0864 0.3488 -0.1478 0.110 Uiso 1 1 calc R U . . .
H12C H -0.0116 0.3543 -0.0370 0.110 Uiso 1 1 calc R U . . .
C13 C -0.1201(10) 0.1526(6) -0.1104(8) 0.069(3) Uani 1 1 d D . . . .
H13A H -0.1828 0.1620 -0.1617 0.103 Uiso 1 1 calc R U . . .
H13B H -0.0465 0.1631 -0.1447 0.103 Uiso 1 1 calc R U . . .
H13C H -0.1210 0.1100 -0.0936 0.103 Uiso 1 1 calc R U . . .
C14 C -0.2589(10) 0.1098(6) 0.0765(12) 0.075(3) Uani 1 1 d . . . . .
H14A H -0.3325 0.1042 0.1145 0.112 Uiso 1 1 calc R U . . .
H14B H -0.2593 0.0876 0.0065 0.112 Uiso 1 1 calc R U . . .
H14C H -0.1964 0.0952 0.1237 0.112 Uiso 1 1 calc R U . . .
C15 C 0.3094(9) 0.2077(6) 0.5610(9) 0.065(3) Uani 1 1 d D . . . .
H15A H 0.3200 0.2257 0.6344 0.097 Uiso 1 1 calc R U . . .
H15B H 0.3090 0.1643 0.5679 0.097 Uiso 1 1 calc R U . . .
H15C H 0.3724 0.2199 0.5121 0.097 Uiso 1 1 calc R U . . .
C16 C 0.0814(14) 0.1500(8) 0.6019(13) 0.102(5) Uani 1 1 d . U . . .
H16A H 0.0131 0.1433 0.6477 0.153 Uiso 1 1 calc R U . . .
H16B H 0.0732 0.1285 0.5316 0.153 Uiso 1 1 calc R U . . .
H16C H 0.1496 0.1355 0.6412 0.153 Uiso 1 1 calc R U . . .
C17 C 0.1631(12) 0.3303(7) 0.6123(8) 0.080(4) Uani 1 1 d D . . . .
H17A H 0.0914 0.3163 0.6460 0.119 Uiso 1 1 calc R U . . .
H17B H 0.2273 0.3225 0.6628 0.119 Uiso 1 1 calc R U . . .
H17C H 0.1576 0.3732 0.5983 0.119 Uiso 1 1 calc R U . . .
C18 C 0.2934(10) 0.3802(6) 0.4165(12) 0.072(4) Uani 1 1 d . . . . .
H18A H 0.3661 0.3887 0.3786 0.109 Uiso 1 1 calc R U . . .
H18B H 0.2291 0.3907 0.3678 0.109 Uiso 1 1 calc R U . . .
H18C H 0.2889 0.4038 0.4848 0.109 Uiso 1 1 calc R U . . .
C19 C 0.0776(17) 0.0184(8) 0.166(2) 0.123(6) Uani 1 1 d . U . . .
Cl3 Cl 0.0614(6) 0.4739(3) -0.1989(8) 0.195(4) Uani 1 1 d . . . . .
O1 O -0.0157(6) 0.3684(3) 0.2395(6) 0.0542(18) Uani 1 1 d . . . . .
H1A H -0.0155 0.3744 0.1710 0.081 Uiso 1 1 calc R U . . .
O2 O -0.1328(5) 0.2864(3) 0.0900(5) 0.0436(16) Uani 1 1 d . . . . .
O3 O -0.0384(5) 0.1707(3) 0.0661(6) 0.0474(17) Uani 1 1 d . . . . .
O4 O 0.0508(5) 0.1172(2) 0.2653(6) 0.0453(15) Uani 1 1 d . . . . .
O5 O 0.1848(5) 0.2003(3) 0.4034(5) 0.0438(16) Uani 1 1 d . . . . .
O6 O 0.0841(5) 0.3136(3) 0.4329(5) 0.0491(18) Uani 1 1 d . . . . .
O7 O -0.0423(6) 0.2702(4) -0.0824(6) 0.0583(19) Uani 1 1 d . . . . .
O8 O -0.2421(5) 0.1717(3) 0.0541(6) 0.0533(18) Uani 1 1 d . . . . .
O9 O 0.0938(6) 0.2128(4) 0.5798(6) 0.071(2) Uani 1 1 d . U . . .
O10 O 0.2875(5) 0.3148(3) 0.4449(6) 0.055(2) Uani 1 1 d . . . . .
O11 O 0.1458(12) 0.0346(5) 0.3694(11) 0.131(4) Uani 1 1 d . . . . .
O12 O 0.2498(6) 0.0885(4) 0.2116(10) 0.099(3) Uani 1 1 d . . . . .
F1 F 0.0764(16) 0.0403(7) 0.0659(14) 0.195(8) Uani 1 1 d . U . . .
F2 F 0.1449(10) -0.0348(4) 0.1624(13) 0.159(5) Uani 1 1 d . . . . .
F3 F -0.0267(10) 0.0012(5) 0.1979(16) 0.203(8) Uani 1 1 d . . . . .
S1 S 0.1457(2) 0.06717(12) 0.2625(3) 0.0667(9) Uani 1 1 d . . . . .
Cl2 Cl -0.1810(9) 0.4780(3) -0.1992(14) 0.285(7) Uani 1 1 d . . . . .
C20 C -0.0575(16) 0.5067(9) -0.1480(19) 0.141(7) Uani 1 1 d . . . . .
H20 H -0.0547 0.5505 -0.1620 0.169 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0720(13) 0.4928(5) -0.0051(9) 0.292(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.421(11) . ?
C1 C2 1.513(8) . ?
C1 C6 1.513(8) . ?
C1 H1 0.9800 . ?
C2 O2 1.420(10) . ?
C2 C3 1.511(8) . ?
C2 H2 0.9800 . ?
C3 O3 1.427(11) . ?
C3 C4 1.509(8) . ?
C3 H3 0.9800 . ?
C4 O4 1.479(10) . ?
C4 C5 1.510(8) . ?
C4 H4 0.9800 . ?
C5 O5 1.453(10) . ?
C5 C6 1.504(8) . ?
C5 H5 0.9800 . ?
C6 O6 1.425(11) . ?
C6 H6 0.9800 . ?
C7 O7 1.401(11) . ?
C7 O2 1.432(11) . ?
C7 C8 1.521(9) . ?
C7 C11 1.525(9) . ?
C8 O3 1.428(11) . ?
C8 O8 1.435(11) . ?
C8 C13 1.503(9) . ?
C9 O5 1.425(11) . ?
C9 O9 1.440(12) . ?
C9 C10 1.516(9) . ?
C9 C15 1.517(9) . ?
C10 O10 1.416(11) . ?
C10 O6 1.437(11) . ?
C10 C17 1.518(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O7 1.420(15) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O8 1.402(14) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O9 1.415(16) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O10 1.480(14) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 F1 1.28(3) . ?
C19 F3 1.30(2) . ?
C19 F2 1.40(2) . ?
C19 S1 1.75(2) . ?
Cl3 C20 1.649(19) . ?
O1 H1A 0.8200 . ?
O4 S1 1.545(6) . ?
O11 S1 1.453(11) . ?
O12 S1 1.411(9) . ?
Cl2 C20 1.66(2) . ?
C20 Cl1 1.72(2) . ?
C20 H20 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
O1 C1 C2 110.9(7) . . ?
O1 C1 C6 108.8(6) . . ?
C2 C1 C6 108.4(6) . . ?
O1 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C6 C1 H1 109.6 . . ?
O2 C2 C3 108.3(6) . . ?
O2 C2 C1 109.9(6) . . ?
C3 C2 C1 111.7(7) . . ?
O2 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
O3 C3 C4 108.8(6) . . ?
O3 C3 C2 109.7(6) . . ?
C4 C3 C2 110.7(7) . . ?
O3 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O4 C4 C3 105.5(6) . . ?
O4 C4 C5 108.0(6) . . ?
C3 C4 C5 107.6(6) . . ?
O4 C4 H4 111.8 . . ?
C3 C4 H4 111.8 . . ?
C5 C4 H4 111.8 . . ?
O5 C5 C6 107.0(6) . . ?
O5 C5 C4 107.4(6) . . ?
C6 C5 C4 112.5(7) . . ?
O5 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
O6 C6 C5 107.3(7) . . ?
O6 C6 C1 108.7(6) . . ?
C5 C6 C1 109.4(7) . . ?
O6 C6 H6 110.4 . . ?
C5 C6 H6 110.4 . . ?
C1 C6 H6 110.4 . . ?
O7 C7 O2 109.4(7) . . ?
O7 C7 C8 103.6(7) . . ?
O2 C7 C8 110.5(7) . . ?
O7 C7 C11 113.4(8) . . ?
O2 C7 C11 105.8(7) . . ?
C8 C7 C11 114.3(8) . . ?
O3 C8 O8 108.8(7) . . ?
O3 C8 C13 104.5(7) . . ?
O8 C8 C13 111.4(8) . . ?
O3 C8 C7 111.6(7) . . ?
O8 C8 C7 105.4(7) . . ?
C13 C8 C7 115.2(8) . . ?
O5 C9 O9 109.9(7) . . ?
O5 C9 C10 111.2(7) . . ?
O9 C9 C10 103.1(8) . . ?
O5 C9 C15 105.8(7) . . ?
O9 C9 C15 113.4(8) . . ?
C10 C9 C15 113.6(8) . . ?
O10 C10 O6 109.1(7) . . ?
O10 C10 C9 104.2(7) . . ?
O6 C10 C9 110.7(7) . . ?
O10 C10 C17 113.8(9) . . ?
O6 C10 C17 104.2(7) . . ?
C9 C10 C17 114.9(9) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O7 C12 H12A 109.5 . . ?
O7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O9 C16 H16A 109.5 . . ?
O9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 C19 F3 111(2) . . ?
F1 C19 F2 106.8(18) . . ?
F3 C19 F2 105.3(15) . . ?
F1 C19 S1 112.2(14) . . ?
F3 C19 S1 113.5(17) . . ?
F2 C19 S1 107.0(16) . . ?
C1 O1 H1A 109.5 . . ?
C2 O2 C7 112.9(6) . . ?
C3 O3 C8 113.2(6) . . ?
C4 O4 S1 124.0(5) . . ?
C9 O5 C5 111.7(6) . . ?
C6 O6 C10 113.2(6) . . ?
C7 O7 C12 116.8(8) . . ?
C14 O8 C8 116.7(8) . . ?
C16 O9 C9 114.8(9) . . ?
C10 O10 C18 114.3(7) . . ?
O12 S1 O11 122.3(7) . . ?
O12 S1 O4 111.2(4) . . ?
O11 S1 O4 109.5(6) . . ?
O12 S1 C19 107.5(9) . . ?
O11 S1 C19 105.2(10) . . ?
O4 S1 C19 98.1(7) . . ?
Cl3 C20 Cl2 113.5(15) . . ?
Cl3 C20 Cl1 111.0(13) . . ?
Cl2 C20 Cl1 102.0(12) . . ?
Cl3 C20 H20 110.0 . . ?
Cl2 C20 H20 110.0 . . ?
Cl1 C20 H20 110.0 . . ?

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
C5 H5 O10 0.98 2.65 3.583(11) 158.6 4_455
C14 H14A O1 0.96 2.63 3.537(14) 158.1 4_455
C18 H18A O4 0.96 2.50 3.436(14) 165.3 4
C18 H18C F2 0.96 2.61 3.525(17) 160.1 3
C20 H20 O1 0.98 2.28 3.167(19) 150.4 2_564
C5 H5 O10 0.98 2.65 3.583(11) 158.6 4_455
C14 H14A O1 0.96 2.63 3.537(14) 158.1 4_455
C18 H18A O4 0.96 2.50 3.436(14) 165.3 4
C18 H18C F2 0.96 2.61 3.525(17) 160.1 3
C20 H20 O1 0.98 2.28 3.167(19) 150.4 2_564

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532607'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H32 O10, 2(O)'
_chemical_formula_sum            'C18 H32 O12'
_chemical_formula_weight         440.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   25.8732(15)
_cell_length_b                   7.1173(4)
_cell_length_c                   12.9798(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.770(2)
_cell_angle_gamma                90
_cell_volume                     2134.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2418
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.09

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.371
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            8642
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2099
_reflns_number_gt                1399
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2099
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_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_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
C1 C 0.01725(8) 0.5204(3) 0.90465(16) 0.0292(5) Uani 1 1 d . . . . .
H1 H 0.0203 0.6038 0.8475 0.035 Uiso 1 1 calc R U . . .
C2 C 0.05218(8) 0.6017(3) 1.02488(16) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.0392 0.7306 1.0261 0.033 Uiso 1 1 calc R U . . .
C3 C -0.04534(8) 0.5115(3) 0.88369(16) 0.0280(5) Uani 1 1 d . . . . .
H3 H -0.0593 0.6395 0.8835 0.034 Uiso 1 1 calc R U . . .
C4 C -0.13977(9) 0.4182(3) 0.74417(17) 0.0312(5) Uani 1 1 d . . . . .
C5 C -0.16839(10) 0.3182(3) 0.62844(18) 0.0432(6) Uani 1 1 d . . . . .
H5A H -0.2095 0.3154 0.6018 0.065 Uiso 1 1 calc R U . . .
H5B H -0.1539 0.1920 0.6370 0.065 Uiso 1 1 calc R U . . .
H5C H -0.1598 0.3841 0.5735 0.065 Uiso 1 1 calc R U . . .
C6 C -0.15721(11) 0.7278(3) 0.6610(2) 0.0505(6) Uani 1 1 d . . . . .
H6A H -0.1193 0.7181 0.6653 0.076 Uiso 1 1 calc R U . . .
H6B H -0.1633 0.8537 0.6798 0.076 Uiso 1 1 calc R U . . .
H6C H -0.1858 0.6978 0.5842 0.076 Uiso 1 1 calc R U . . .
C7 C 0.14851(8) 0.6835(3) 1.15886(16) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.20947(9) 0.6622(3) 1.17290(19) 0.0423(5) Uani 1 1 d . . . . .
H8A H 0.2133 0.7309 1.1130 0.063 Uiso 1 1 calc R U . . .
H8B H 0.2174 0.5318 1.1678 0.063 Uiso 1 1 calc R U . . .
H8C H 0.2364 0.7105 1.2468 0.063 Uiso 1 1 calc R U . . .
C9 C 0.13336(12) 0.9952(3) 1.0772(2) 0.0554(7) Uani 1 1 d . . . . .
H9A H 0.1718 1.0036 1.0839 0.083 Uiso 1 1 calc R U . . .
H9B H 0.1205 1.1179 1.0862 0.083 Uiso 1 1 calc R U . . .
H9C H 0.1076 0.9461 1.0026 0.083 Uiso 1 1 calc R U . . .
O1 O 0.03735(6) 0.33853(19) 0.89558(12) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.0528 0.3426 0.8526 0.057 Uiso 1 1 calc R U . . .
O2 O 0.11183(5) 0.60561(18) 1.04949(11) 0.0314(4) Uani 1 1 d . . . . .
O3 O -0.07972(6) 0.42709(18) 0.77279(11) 0.0304(4) Uani 1 1 d . . . . .
O4 O -0.16201(6) 0.60009(18) 0.74064(12) 0.0365(4) Uani 1 1 d . . . . .
O5 O 0.13355(6) 0.87315(19) 1.16483(12) 0.0410(4) Uani 1 1 d . . . . .
O1'' O 0.02693(16) 1.0225(4) 1.1765(3) 0.1462(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.419(2) . ?
C1 C3 1.518(3) . ?
C1 C2 1.522(3) . ?
C1 H1 0.9800 . ?
C2 O2 1.428(2) . ?
C2 C3 1.509(3) 5_567 ?
C2 H2 0.9800 . ?
C3 O3 1.439(2) . ?
C3 C2 1.509(3) 5_567 ?
C3 H3 0.9800 . ?
C4 O4 1.409(2) . ?
C4 O3 1.427(2) . ?
C4 C5 1.520(3) . ?
C4 C7 1.554(3) 5_567 ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O4 1.423(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O5 1.416(2) . ?
C7 O2 1.418(2) . ?
C7 C8 1.512(3) . ?
C7 C4 1.554(3) 5_567 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O5 1.429(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O1 H1A 0.8200 . ?

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 C1 C3 110.38(15) . . ?
O1 C1 C2 111.17(16) . . ?
C3 C1 C2 107.02(14) . . ?
O1 C1 H1 109.4 . . ?
C3 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O2 C2 C3 109.40(15) . 5_567 ?
O2 C2 C1 108.65(13) . . ?
C3 C2 C1 112.17(15) 5_567 . ?
O2 C2 H2 108.9 . . ?
C3 C2 H2 108.9 5_567 . ?
C1 C2 H2 108.9 . . ?
O3 C3 C2 108.98(15) . 5_567 ?
O3 C3 C1 109.00(14) . . ?
C2 C3 C1 112.02(16) 5_567 . ?
O3 C3 H3 108.9 . . ?
C2 C3 H3 108.9 5_567 . ?
C1 C3 H3 108.9 . . ?
O4 C4 O3 110.41(15) . . ?
O4 C4 C5 112.84(17) . . ?
O3 C4 C5 105.47(15) . . ?
O4 C4 C7 104.36(15) . 5_567 ?
O3 C4 C7 110.38(15) . 5_567 ?
C5 C4 C7 113.48(16) . 5_567 ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 O2 110.58(15) . . ?
O5 C7 C8 112.64(16) . . ?
O2 C7 C8 105.84(15) . . ?
O5 C7 C4 104.88(15) . 5_567 ?
O2 C7 C4 110.66(15) . 5_567 ?
C8 C7 C4 112.35(17) . 5_567 ?
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 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 O1 H1A 109.5 . . ?
C7 O2 C2 113.58(13) . . ?
C4 O3 C3 112.88(13) . . ?
C4 O4 C6 116.26(15) . . ?
C7 O5 C9 116.04(15) . . ?

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
C6 H6B O5 0.96 2.65 3.508(3) 148.4 5_577
O1 H1A O3 0.82 2.13 2.9212(18) 163.5 2_556

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532604'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H30 N6 O8'
_chemical_formula_sum            'C18 H30 N6 O8'
_chemical_formula_weight         458.48
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.3487(4)
_cell_length_b                   22.2829(8)
_cell_length_c                   17.8108(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.944(2)
_cell_angle_gamma                90
_cell_volume                     4712.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7109
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.291
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            40102
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9644
_reflns_number_gt                5240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9644
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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_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
C1A C 0.53576(16) 0.05206(10) 0.40866(12) 0.0405(5) Uani 1 1 d . . . . .
H1A H 0.5542 0.0476 0.4655 0.049 Uiso 1 1 calc R U . . .
C1B C 0.06471(18) 0.19322(11) 0.79285(13) 0.0477(6) Uani 1 1 d . . . . .
H1B H 0.0995 0.2318 0.8120 0.057 Uiso 1 1 calc R U . . .
C2A C 0.41356(16) 0.07129(10) 0.37639(12) 0.0408(5) Uani 1 1 d . . . . .
H2A H 0.4010 0.1089 0.4014 0.049 Uiso 1 1 calc R U . . .
C2B C 0.15195(17) 0.14382(10) 0.81218(12) 0.0428(5) Uani 1 1 d . . . . .
H2B H 0.1164 0.1058 0.7910 0.051 Uiso 1 1 calc R U . . .
C3A C 0.38644(16) 0.08046(10) 0.28912(12) 0.0401(5) Uani 1 1 d . . . . .
H3A H 0.4015 0.0431 0.2647 0.048 Uiso 1 1 calc R U . . .
C3B C 0.20186(17) 0.13722(11) 0.89919(12) 0.0467(6) Uani 1 1 d . . . . .
H3B H 0.2366 0.1753 0.9208 0.056 Uiso 1 1 calc R U . . .
C4A C 0.45755(16) 0.13040(10) 0.26917(12) 0.0412(5) Uani 1 1 d . . . . .
H4A H 0.4433 0.1682 0.2929 0.049 Uiso 1 1 calc R U . . .
C4B C 0.11154(18) 0.12028(11) 0.93880(13) 0.0491(6) Uani 1 1 d . . . . .
H4B H 0.1441 0.1180 0.9955 0.059 Uiso 1 1 calc R U . . .
C5A C 0.58011(16) 0.11245(10) 0.30086(12) 0.0409(5) Uani 1 1 d . . . . .
H5A H 0.5945 0.0760 0.2743 0.049 Uiso 1 1 calc R U . . .
C5B C 0.02234(18) 0.16879(11) 0.91885(14) 0.0510(6) Uani 1 1 d . . . . .
H5B H 0.0568 0.2066 0.9417 0.061 Uiso 1 1 calc R U . . .
C6A C 0.60694(16) 0.10079(10) 0.38765(12) 0.0411(5) Uani 1 1 d . . . . .
H6A H 0.5936 0.1380 0.4131 0.049 Uiso 1 1 calc R U . . .
C6B C -0.02597(18) 0.17808(11) 0.83223(14) 0.0498(6) Uani 1 1 d . . . . .
H6B H -0.0642 0.1412 0.8091 0.060 Uiso 1 1 calc R U . . .
C7A C 0.22449(17) 0.03652(12) 0.36132(14) 0.0531(6) Uani 1 1 d . . . . .
C7B C 0.32494(19) 0.11259(11) 0.79043(14) 0.0516(6) Uani 1 1 d . . . . .
C8A C 0.1669(2) -0.01919(13) 0.38037(17) 0.0764(9) Uani 1 1 d . . . . .
H8A1 H 0.1913 -0.0535 0.3568 0.115 Uiso 1 1 calc R U . . .
H8A2 H 0.1862 -0.0245 0.4360 0.115 Uiso 1 1 calc R U . . .
H8A3 H 0.0868 -0.0148 0.3604 0.115 Uiso 1 1 calc R U . . .
C8B C 0.4114(2) 0.13586(14) 0.75135(16) 0.0709(8) Uani 1 1 d . . . . .
H8B1 H 0.4400 0.1738 0.7739 0.106 Uiso 1 1 calc R U . . .
H8B2 H 0.4723 0.1077 0.7590 0.106 Uiso 1 1 calc R U . . .
H8B3 H 0.3767 0.1409 0.6965 0.106 Uiso 1 1 calc R U . . .
C9A C 0.2146(2) 0.09145(17) 0.47603(16) 0.0880(10) Uani 1 1 d . . . . .
H9A1 H 0.1902 0.1295 0.4908 0.132 Uiso 1 1 calc R U . . .
H9A2 H 0.1737 0.0598 0.4927 0.132 Uiso 1 1 calc R U . . .
H9A3 H 0.2937 0.0866 0.5003 0.132 Uiso 1 1 calc R U . . .
C9B C 0.2143(2) 0.05610(14) 0.68073(16) 0.0790(9) Uani 1 1 d . . . . .
H9B1 H 0.1865 0.0163 0.6666 0.118 Uiso 1 1 calc R U . . .
H9B2 H 0.1520 0.0834 0.6732 0.118 Uiso 1 1 calc R U . . .
H9B3 H 0.2614 0.0681 0.6485 0.118 Uiso 1 1 calc R U . . .
C10A C 0.19770(18) 0.04948(11) 0.27258(14) 0.0524(6) Uani 1 1 d . . . . .
C10B C 0.37434(19) 0.10222(13) 0.87919(14) 0.0571(7) Uani 1 1 d . . . . .
C11A C 0.07880(18) 0.07233(14) 0.23773(16) 0.0716(8) Uani 1 1 d . . . . .
H11A H 0.0688 0.1094 0.2624 0.107 Uiso 1 1 calc R U . . .
H11B H 0.0664 0.0788 0.1827 0.107 Uiso 1 1 calc R U . . .
H11C H 0.0259 0.0432 0.2460 0.107 Uiso 1 1 calc R U . . .
C11B C 0.4505(2) 0.04806(16) 0.89826(18) 0.0889(10) Uani 1 1 d . . . . .
H11D H 0.4085 0.0127 0.8776 0.133 Uiso 1 1 calc R U . . .
H11E H 0.5119 0.0528 0.8754 0.133 Uiso 1 1 calc R U . . .
H11F H 0.4794 0.0443 0.9539 0.133 Uiso 1 1 calc R U . . .
C12B C 0.4739(3) 0.1612(2) 0.98962(19) 0.1291(17) Uani 1 1 d . . . . .
H12A H 0.5091 0.1997 1.0023 0.194 Uiso 1 1 calc R U . . .
H12B H 0.4142 0.1571 1.0142 0.194 Uiso 1 1 calc R U . . .
H12C H 0.5286 0.1302 1.0079 0.194 Uiso 1 1 calc R U . . .
C13A C 0.2104(3) -0.00475(14) 0.15778(16) 0.0808(9) Uani 1 1 d . . . . .
H13A H 0.2269 -0.0440 0.1418 0.121 Uiso 1 1 calc R U . . .
H13B H 0.1353 0.0064 0.1293 0.121 Uiso 1 1 calc R U . . .
H13C H 0.2629 0.0236 0.1473 0.121 Uiso 1 1 calc R U . . .
C13B C -0.1512(2) 0.19929(12) 0.93980(19) 0.0678(8) Uani 1 1 d . . . . .
C14A C 0.76750(17) 0.14613(11) 0.31542(14) 0.0494(6) Uani 1 1 d . . . . .
C14B C -0.2402(3) 0.17436(15) 0.9762(2) 0.0912(10) Uani 1 1 d . . . . .
H14A H -0.2692 0.1374 0.9509 0.137 Uiso 1 1 calc R U . . .
H14B H -0.2069 0.1672 1.0308 0.137 Uiso 1 1 calc R U . . .
H14C H -0.3004 0.2028 0.9697 0.137 Uiso 1 1 calc R U . . .
C15A C 0.8304(2) 0.20036(12) 0.29770(18) 0.0682(8) Uani 1 1 d . . . . .
H15A H 0.8107 0.2351 0.3230 0.102 Uiso 1 1 calc R U . . .
H15B H 0.9100 0.1934 0.3166 0.102 Uiso 1 1 calc R U . . .
H15C H 0.8104 0.2069 0.2423 0.102 Uiso 1 1 calc R U . . .
C15B C -0.0541(4) 0.25265(18) 1.0561(3) 0.1265(15) Uani 1 1 d . . . . .
H15D H -0.0254 0.2918 1.0736 0.190 Uiso 1 1 calc R U . . .
H15E H -0.1093 0.2411 1.0823 0.190 Uiso 1 1 calc R U . . .
H15F H 0.0065 0.2242 1.0677 0.190 Uiso 1 1 calc R U . . .
C16A C 0.7677(2) 0.09364(14) 0.19738(16) 0.0783(9) Uani 1 1 d . . . . .
H16A H 0.7874 0.0556 0.1796 0.117 Uiso 1 1 calc R U . . .
H16B H 0.6888 0.1010 0.1750 0.117 Uiso 1 1 calc R U . . .
H16C H 0.8105 0.1248 0.1817 0.117 Uiso 1 1 calc R U . . .
C16B C -0.1979(2) 0.21271(11) 0.85208(18) 0.0629(7) Uani 1 1 d . . . . .
C17A C 0.79638(17) 0.13123(11) 0.40355(14) 0.0501(6) Uani 1 1 d . . . . .
C17B C -0.2748(2) 0.26663(14) 0.8343(2) 0.0924(10) Uani 1 1 d . . . . .
H17A H -0.2343 0.3017 0.8581 0.139 Uiso 1 1 calc R U . . .
H17B H -0.3008 0.2723 0.7788 0.139 Uiso 1 1 calc R U . . .
H17C H -0.3381 0.2602 0.8548 0.139 Uiso 1 1 calc R U . . .
C18A C 0.91521(18) 0.10644(13) 0.43612(17) 0.0731(8) Uani 1 1 d . . . . .
H18A H 0.9227 0.0698 0.4096 0.110 Uiso 1 1 calc R U . . .
H18B H 0.9689 0.1353 0.4284 0.110 Uiso 1 1 calc R U . . .
H18C H 0.9288 0.0986 0.4909 0.110 Uiso 1 1 calc R U . . .
C18B C -0.2956(2) 0.15827(16) 0.7362(2) 0.0951(11) Uani 1 1 d . . . . .
H18D H -0.3305 0.1201 0.7203 0.143 Uiso 1 1 calc R U . . .
H18E H -0.3505 0.1896 0.7199 0.143 Uiso 1 1 calc R U . . .
H18F H -0.2353 0.1643 0.7126 0.143 Uiso 1 1 calc R U . . .
C19A C 0.7911(3) 0.18207(16) 0.52152(18) 0.1031(12) Uani 1 1 d . . . . .
H19A H 0.7771 0.2209 0.5403 0.155 Uiso 1 1 calc R U . . .
H19B H 0.7385 0.1536 0.5316 0.155 Uiso 1 1 calc R U . . .
H19C H 0.8664 0.1696 0.5478 0.155 Uiso 1 1 calc R U . . .
N1A N 0.55760(14) -0.00536(9) 0.37234(11) 0.0489(5) Uani 1 1 d . . . . .
N1B N 0.01033(17) 0.19663(11) 0.70776(13) 0.0690(6) Uani 1 1 d . . . . .
N2A N 0.52043(15) -0.05011(10) 0.39591(11) 0.0487(5) Uani 1 1 d . . . . .
N2B N 0.0680(2) 0.21850(12) 0.66849(14) 0.0758(7) Uani 1 1 d . . . . .
N3A N 0.4923(2) -0.09535(11) 0.41290(14) 0.0736(7) Uani 1 1 d . . . . .
N3B N 0.1098(3) 0.23705(17) 0.62498(17) 0.1234(12) Uani 1 1 d . . . . .
N4A N 0.43321(17) 0.13735(10) 0.18329(11) 0.0609(6) Uani 1 1 d . . . . .
N4B N 0.05822(17) 0.06232(10) 0.90855(13) 0.0620(6) Uani 1 1 d . . . . .
N5A N 0.34570(19) 0.16394(11) 0.15204(12) 0.0663(6) Uani 1 1 d . . . . .
N5B N 0.1096(2) 0.01792(13) 0.93831(14) 0.0732(7) Uani 1 1 d . . . . .
N6A N 0.2677(2) 0.18734(14) 0.11605(16) 0.1028(10) Uani 1 1 d . . . . .
N6B N 0.1487(3) -0.02654(15) 0.9608(2) 0.1281(12) Uani 1 1 d . . . . .
O1A O 0.34291(11) 0.02543(7) 0.39336(9) 0.0510(4) Uani 1 1 d . . . . .
O1B O 0.23925(12) 0.15735(7) 0.77679(9) 0.0481(4) Uani 1 1 d . . . . .
O2A O 0.27022(11) 0.09560(7) 0.25864(8) 0.0459(4) Uani 1 1 d . . . . .
O2B O 0.28552(12) 0.09123(8) 0.91476(9) 0.0593(5) Uani 1 1 d . . . . .
O3A O 0.65025(11) 0.15992(7) 0.28730(9) 0.0474(4) Uani 1 1 d . . . . .
O3B O -0.06561(13) 0.15445(7) 0.95317(10) 0.0597(5) Uani 1 1 d . . . . .
O4A O 0.72359(11) 0.08536(7) 0.41766(8) 0.0465(4) Uani 1 1 d . . . . .
O4B O -0.10628(12) 0.22577(7) 0.81948(10) 0.0610(5) Uani 1 1 d . . . . .
O5A O 0.19389(12) 0.08925(8) 0.39346(9) 0.0599(5) Uani 1 1 d . . . . .
O5B O 0.27835(14) 0.05693(8) 0.76099(10) 0.0643(5) Uani 1 1 d . . . . .
O6A O 0.21950(14) -0.00517(8) 0.23944(10) 0.0656(5) Uani 1 1 d . . . . .
O6B O 0.42908(14) 0.15646(10) 0.90738(11) 0.0765(6) Uani 1 1 d . . . . .
O7A O 0.79203(12) 0.09298(7) 0.28018(10) 0.0559(4) Uani 1 1 d . . . . .
O7B O -0.10465(17) 0.25401(9) 0.97440(14) 0.0875(6) Uani 1 1 d . . . . .
O8A O 0.77830(14) 0.18514(8) 0.43957(11) 0.0676(5) Uani 1 1 d . . . . .
O8B O -0.25219(14) 0.15945(8) 0.81876(12) 0.0709(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.491(3) . ?
C1A C6A 1.507(3) . ?
C1A C2A 1.521(3) . ?
C1A H1A 0.9800 . ?
C1B N1B 1.481(3) . ?
C1B C2B 1.512(3) . ?
C1B C6B 1.514(3) . ?
C1B H1B 0.9800 . ?
C2A O1A 1.429(2) . ?
C2A C3A 1.511(3) . ?
C2A H2A 0.9800 . ?
C2B O1B 1.423(2) . ?
C2B C3B 1.509(3) . ?
C2B H2B 0.9800 . ?
C3A O2A 1.428(2) . ?
C3A C4A 1.519(3) . ?
C3A H3A 0.9800 . ?
C3B O2B 1.427(3) . ?
C3B C4B 1.522(3) . ?
C3B H3B 0.9800 . ?
C4A N4A 1.484(3) . ?
C4A C5A 1.516(3) . ?
C4A H4A 0.9800 . ?
C4B N4B 1.482(3) . ?
C4B C5B 1.514(3) . ?
C4B H4B 0.9800 . ?
C5A O3A 1.429(2) . ?
C5A C6A 1.512(3) . ?
C5A H5A 0.9800 . ?
C5B O3B 1.421(3) . ?
C5B C6B 1.508(3) . ?
C5B H5B 0.9800 . ?
C6A O4A 1.434(2) . ?
C6A H6A 0.9800 . ?
C6B O4B 1.429(3) . ?
C6B H6B 0.9800 . ?
C7A O5A 1.403(3) . ?
C7A O1A 1.438(2) . ?
C7A C8A 1.515(3) . ?
C7A C10A 1.550(3) . ?
C7B O5B 1.406(3) . ?
C7B O1B 1.426(3) . ?
C7B C8B 1.517(3) . ?
C7B C10B 1.547(3) . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 0.9600 . ?
C8B H8B1 0.9600 . ?
C8B H8B2 0.9600 . ?
C8B H8B3 0.9600 . ?
C9A O5A 1.423(3) . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 0.9600 . ?
C9B O5B 1.431(3) . ?
C9B H9B1 0.9600 . ?
C9B H9B2 0.9600 . ?
C9B H9B3 0.9600 . ?
C10A O6A 1.411(3) . ?
C10A O2A 1.429(3) . ?
C10A C11A 1.516(3) . ?
C10B O6B 1.408(3) . ?
C10B O2B 1.431(3) . ?
C10B C11B 1.510(4) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B O6B 1.420(3) . ?
C12B H12A 0.9600 . ?
C12B H12B 0.9600 . ?
C12B H12C 0.9600 . ?
C13A O6A 1.428(3) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C13B O7B 1.415(3) . ?
C13B O3B 1.426(3) . ?
C13B C14B 1.525(4) . ?
C13B C16B 1.539(4) . ?
C14A O7A 1.412(3) . ?
C14A O3A 1.429(2) . ?
C14A C15A 1.516(3) . ?
C14A C17A 1.547(3) . ?
C14B H14A 0.9600 . ?
C14B H14B 0.9600 . ?
C14B H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B O7B 1.417(4) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16A O7A 1.422(3) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16B O8B 1.411(3) . ?
C16B O4B 1.436(3) . ?
C16B C17B 1.510(4) . ?
C17A O8A 1.408(3) . ?
C17A O4A 1.428(3) . ?
C17A C18A 1.525(3) . ?
C17B H17A 0.9600 . ?
C17B H17B 0.9600 . ?
C17B H17C 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C18B O8B 1.420(3) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19A O8A 1.426(3) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
N1A N2A 1.219(3) . ?
N1B N2B 1.228(3) . ?
N2A N3A 1.134(3) . ?
N2B N3B 1.121(3) . ?
N4A N5A 1.224(3) . ?
N4B N5B 1.216(3) . ?
N5A N6A 1.128(3) . ?
N5B N6B 1.126(4) . ?

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
N1A C1A C6A 108.85(16) . . ?
N1A C1A C2A 110.89(17) . . ?
C6A C1A C2A 106.79(17) . . ?
N1A C1A H1A 110.1 . . ?
C6A C1A H1A 110.1 . . ?
C2A C1A H1A 110.1 . . ?
N1B C1B C2B 111.39(19) . . ?
N1B C1B C6B 107.48(18) . . ?
C2B C1B C6B 107.67(18) . . ?
N1B C1B H1B 110.1 . . ?
C2B C1B H1B 110.1 . . ?
C6B C1B H1B 110.1 . . ?
O1A C2A C3A 109.79(17) . . ?
O1A C2A C1A 108.57(17) . . ?
C3A C2A C1A 110.07(16) . . ?
O1A C2A H2A 109.5 . . ?
C3A C2A H2A 109.5 . . ?
C1A C2A H2A 109.5 . . ?
O1B C2B C3B 109.28(16) . . ?
O1B C2B C1B 108.90(17) . . ?
C3B C2B C1B 111.66(18) . . ?
O1B C2B H2B 109.0 . . ?
C3B C2B H2B 109.0 . . ?
C1B C2B H2B 109.0 . . ?
O2A C3A C2A 109.78(15) . . ?
O2A C3A C4A 108.85(16) . . ?
C2A C3A C4A 111.14(16) . . ?
O2A C3A H3A 109.0 . . ?
C2A C3A H3A 109.0 . . ?
C4A C3A H3A 109.0 . . ?
O2B C3B C2B 109.83(17) . . ?
O2B C3B C4B 108.38(18) . . ?
C2B C3B C4B 110.82(17) . . ?
O2B C3B H3B 109.3 . . ?
C2B C3B H3B 109.3 . . ?
C4B C3B H3B 109.3 . . ?
N4A C4A C5A 108.07(16) . . ?
N4A C4A C3A 110.57(17) . . ?
C5A C4A C3A 107.56(17) . . ?
N4A C4A H4A 110.2 . . ?
C5A C4A H4A 110.2 . . ?
C3A C4A H4A 110.2 . . ?
N4B C4B C5B 108.35(19) . . ?
N4B C4B C3B 110.88(19) . . ?
C5B C4B C3B 107.02(19) . . ?
N4B C4B H4B 110.2 . . ?
C5B C4B H4B 110.2 . . ?
C3B C4B H4B 110.2 . . ?
O3A C5A C6A 109.10(16) . . ?
O3A C5A C4A 109.34(17) . . ?
C6A C5A C4A 109.99(16) . . ?
O3A C5A H5A 109.5 . . ?
C6A C5A H5A 109.5 . . ?
C4A C5A H5A 109.5 . . ?
O3B C5B C6B 109.68(18) . . ?
O3B C5B C4B 109.34(19) . . ?
C6B C5B C4B 113.32(18) . . ?
O3B C5B H5B 108.1 . . ?
C6B C5B H5B 108.1 . . ?
C4B C5B H5B 108.1 . . ?
O4A C6A C1A 109.22(17) . . ?
O4A C6A C5A 109.75(16) . . ?
C1A C6A C5A 113.49(17) . . ?
O4A C6A H6A 108.1 . . ?
C1A C6A H6A 108.1 . . ?
C5A C6A H6A 108.1 . . ?
O4B C6B C5B 109.09(19) . . ?
O4B C6B C1B 109.28(18) . . ?
C5B C6B C1B 111.70(18) . . ?
O4B C6B H6B 108.9 . . ?
C5B C6B H6B 108.9 . . ?
C1B C6B H6B 108.9 . . ?
O5A C7A O1A 109.91(19) . . ?
O5A C7A C8A 113.53(19) . . ?
O1A C7A C8A 105.01(19) . . ?
O5A C7A C10A 104.71(19) . . ?
O1A C7A C10A 110.22(16) . . ?
C8A C7A C10A 113.5(2) . . ?
O5B C7B O1B 110.18(18) . . ?
O5B C7B C8B 113.4(2) . . ?
O1B C7B C8B 105.4(2) . . ?
O5B C7B C10B 104.8(2) . . ?
O1B C7B C10B 110.15(18) . . ?
C8B C7B C10B 113.0(2) . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
O5A C9A H9A1 109.5 . . ?
O5A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
O5A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
O5B C9B H9B1 109.5 . . ?
O5B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
O5B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
O6A C10A O2A 110.32(17) . . ?
O6A C10A C11A 113.1(2) . . ?
O2A C10A C11A 105.66(19) . . ?
O6A C10A C7A 104.71(19) . . ?
O2A C10A C7A 110.04(18) . . ?
C11A C10A C7A 113.03(19) . . ?
O6B C10B O2B 109.9(2) . . ?
O6B C10B C11B 113.4(2) . . ?
O2B C10B C11B 105.6(2) . . ?
O6B C10B C7B 104.6(2) . . ?
O2B C10B C7B 110.06(18) . . ?
C11B C10B C7B 113.3(2) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
O6B C12B H12A 109.5 . . ?
O6B C12B H12B 109.5 . . ?
H12A C12B H12B 109.5 . . ?
O6B C12B H12C 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
O6A C13A H13A 109.5 . . ?
O6A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
O6A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O7B C13B O3B 109.7(2) . . ?
O7B C13B C14B 112.5(2) . . ?
O3B C13B C14B 105.1(2) . . ?
O7B C13B C16B 105.6(2) . . ?
O3B C13B C16B 111.1(2) . . ?
C14B C13B C16B 112.9(2) . . ?
O7A C14A O3A 110.18(18) . . ?
O7A C14A C15A 113.03(19) . . ?
O3A C14A C15A 106.47(18) . . ?
O7A C14A C17A 104.67(18) . . ?
O3A C14A C17A 109.31(16) . . ?
C15A C14A C17A 113.2(2) . . ?
C13B C14B H14A 109.5 . . ?
C13B C14B H14B 109.5 . . ?
H14A C14B H14B 109.5 . . ?
C13B C14B H14C 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O7B C15B H15D 109.5 . . ?
O7B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O7B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O7A C16A H16A 109.5 . . ?
O7A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
O7A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
O8B C16B O4B 109.7(2) . . ?
O8B C16B C17B 112.5(2) . . ?
O4B C16B C17B 105.9(2) . . ?
O8B C16B C13B 105.4(2) . . ?
O4B C16B C13B 109.5(2) . . ?
C17B C16B C13B 113.9(2) . . ?
O8A C17A O4A 110.12(17) . . ?
O8A C17A C18A 113.1(2) . . ?
O4A C17A C18A 105.08(19) . . ?
O8A C17A C14A 104.94(19) . . ?
O4A C17A C14A 110.57(17) . . ?
C18A C17A C14A 113.2(2) . . ?
C16B C17B H17A 109.5 . . ?
C16B C17B H17B 109.5 . . ?
H17A C17B H17B 109.5 . . ?
C16B C17B H17C 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O8B C18B H18D 109.5 . . ?
O8B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
O8B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O8A C19A H19A 109.5 . . ?
O8A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
O8A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
N2A N1A C1A 114.98(17) . . ?
N2B N1B C1B 115.6(2) . . ?
N3A N2A N1A 172.1(2) . . ?
N3B N2B N1B 171.5(3) . . ?
N5A N4A C4A 115.0(2) . . ?
N5B N4B C4B 115.1(2) . . ?
N6A N5A N4A 172.8(3) . . ?
N6B N5B N4B 172.9(3) . . ?
C2A O1A C7A 113.99(16) . . ?
C2B O1B C7B 113.18(16) . . ?
C3A O2A C10A 112.11(16) . . ?
C3B O2B C10B 113.15(17) . . ?
C5A O3A C14A 112.59(16) . . ?
C5B O3B C13B 112.93(18) . . ?
C17A O4A C6A 112.28(16) . . ?
C6B O4B C16B 111.99(18) . . ?
C7A O5A C9A 117.3(2) . . ?
C7B O5B C9B 116.2(2) . . ?
C10A O6A C13A 116.7(2) . . ?
C10B O6B C12B 116.4(3) . . ?
C14A O7A C16A 116.3(2) . . ?
C13B O7B C15B 116.1(3) . . ?
C17A O8A C19A 116.0(2) . . ?
C16B O8B C18B 116.8(2) . . ?

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
C1A H1A N3A 0.98 2.61 3.429(3) 140.7 3_656
C1B H1B O3A 0.98 2.56 3.448(3) 150.7 4_566
C4A H4A O4B 0.98 2.52 3.476(3) 165.8 4_665
C9A H9A3 N2A 0.96 2.65 3.558(3) 158.3 3_656
C9A H9A3 N3A 0.96 2.68 3.618(4) 166.7 3_656
C9B H9B1 O7A 0.96 2.60 3.399(4) 141.0 3_656
C12B H12A N3B 0.96 2.61 3.398(5) 139.5 4_666
C15A H15A O1B 0.96 2.61 3.351(3) 134.4 4_665
C15B H15D N3A 0.96 2.55 3.483(5) 164.1 2_556
C19A H19A N6A 0.96 2.47 3.414(4) 167.5 4_666

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_newpn1
_database_code_depnum_ccdc_archive 'CCDC 1532603'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H32 O10'
_chemical_formula_sum            'C18 H32 O10'
_chemical_formula_weight         408.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Pn   '
_symmetry_space_group_name_Hall  'P -2yac '

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

_cell_length_a                   6.7657(3)
_cell_length_b                   13.1376(7)
_cell_length_c                   11.8254(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.583(2)
_cell_angle_gamma                90.00
_cell_volume                     1007.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3131
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.346
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7360
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         24.98
_reflns_number_total             3425
_reflns_number_gt                2792
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.1044P)²+0.3266P] 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   -1.4(16)
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8874(5) 0.2192(3) 0.8425(3) 0.0266(8) Uani 1 1 d . . .
H1 H 0.9896 0.1721 0.8277 0.032 Uiso 1 1 calc R . .
C2 C 0.7377(5) 0.1609(3) 0.8950(3) 0.0250(8) Uani 1 1 d . . .
H2 H 0.6767 0.1047 0.8421 0.030 Uiso 1 1 calc R . .
C3 C 0.5662(5) 0.2281(3) 0.9116(4) 0.0308(9) Uani 1 1 d . . .
H3 H 0.6251 0.2819 0.9687 0.037 Uiso 1 1 calc R . .
C4 C 0.4409(5) 0.2759(3) 0.7964(3) 0.0285(8) Uani 1 1 d . . .
H4 H 0.3662 0.2232 0.7422 0.034 Uiso 1 1 calc R . .
C5 C 0.5858(6) 0.3306(3) 0.7436(3) 0.0290(8) Uani 1 1 d . . .
H5 H 0.6456 0.3885 0.7941 0.035 Uiso 1 1 calc R . .
C6 C 0.7588(5) 0.2643(3) 0.7270(3) 0.0250(8) Uani 1 1 d . . .
H6 H 0.7000 0.2091 0.6719 0.030 Uiso 1 1 calc R . .
C7 C 0.7265(5) 0.0580(3) 1.0582(3) 0.0332(9) Uani 1 1 d . . .
C8 C 0.8006(8) -0.0877(4) 0.9593(5) 0.0598(14) Uani 1 1 d . . .
H8A H 0.9226 -0.0484 0.9644 0.090 Uiso 1 1 calc R . .
H8B H 0.7468 -0.1137 0.8807 0.090 Uiso 1 1 calc R . .
H8C H 0.8342 -0.1433 1.0141 0.090 Uiso 1 1 calc R . .
C9 C 0.8669(7) 0.0288(4) 1.1799(4) 0.0570(13) Uani 1 1 d . . .
H9A H 0.7959 -0.0181 1.2169 0.086 Uiso 1 1 calc R . .
H9B H 0.9029 0.0887 1.2278 0.086 Uiso 1 1 calc R . .
H9C H 0.9899 -0.0027 1.1713 0.086 Uiso 1 1 calc R . .
C10 C 0.5327(6) 0.1179(3) 1.0666(4) 0.0394(10) Uani 1 1 d . . .
C11 C 0.3723(7) 0.0533(4) 1.0958(5) 0.0583(14) Uani 1 1 d . . .
H11A H 0.2590 0.0953 1.1008 0.088 Uiso 1 1 calc R . .
H11B H 0.4308 0.0201 1.1701 0.088 Uiso 1 1 calc R . .
H11C H 0.3240 0.0031 1.0353 0.088 Uiso 1 1 calc R . .
C12 C 0.4653(9) 0.2637(5) 1.1735(5) 0.0701(16) Uani 1 1 d . . .
H12A H 0.3609 0.2269 1.1970 0.105 Uiso 1 1 calc R . .
H12B H 0.4027 0.3012 1.1026 0.105 Uiso 1 1 calc R . .
H12C H 0.5335 0.3100 1.2351 0.105 Uiso 1 1 calc R . .
C13 C 0.5903(6) 0.4290(3) 0.5750(3) 0.0345(9) Uani 1 1 d . . .
C14 C 0.4470(6) 0.4557(4) 0.4554(3) 0.0406(10) Uani 1 1 d . . .
H14A H 0.4042 0.3945 0.4107 0.061 Uiso 1 1 calc R . .
H14B H 0.5174 0.4991 0.4143 0.061 Uiso 1 1 calc R . .
H14C H 0.3281 0.4904 0.4653 0.061 Uiso 1 1 calc R . .
C15 C 0.5150(8) 0.5798(4) 0.6745(4) 0.0498(12) Uani 1 1 d . . .
H15A H 0.4203 0.6045 0.6030 0.075 Uiso 1 1 calc R . .
H15B H 0.5822 0.6363 0.7214 0.075 Uiso 1 1 calc R . .
H15C H 0.4411 0.5411 0.7181 0.075 Uiso 1 1 calc R . .
C16 C 0.7830(6) 0.3697(3) 0.5662(3) 0.0357(10) Uani 1 1 d . . .
C17 C 0.9407(8) 0.4395(4) 0.5358(5) 0.0629(16) Uani 1 1 d . . .
H17A H 1.0668 0.4028 0.5444 0.094 Uiso 1 1 calc R . .
H17B H 0.9667 0.4971 0.5880 0.094 Uiso 1 1 calc R . .
H17C H 0.8878 0.4627 0.4558 0.094 Uiso 1 1 calc R . .
C18 C 0.8533(10) 0.2266(5) 0.4560(6) 0.085(2) Uani 1 1 d . . .
H18A H 0.9169 0.2609 0.4037 0.128 Uiso 1 1 calc R . .
H18B H 0.7864 0.1659 0.4187 0.128 Uiso 1 1 calc R . .
H18C H 0.9567 0.2089 0.5275 0.128 Uiso 1 1 calc R . .
O1 O 0.9874(4) 0.2948(2) 0.9227(2) 0.0482(7) Uani 1 1 d . . .
H1' H 1.0984 0.3086 0.9113 0.072 Uiso 1 1 calc R . .
O2 O 0.8498(4) 0.1201(2) 1.0067(2) 0.0334(6) Uani 1 1 d . . .
O3 O 0.4306(3) 0.1655(2) 0.9567(2) 0.0354(7) Uani 1 1 d . . .
O4 O 0.3016(4) 0.3442(2) 0.8232(2) 0.0424(6) Uani 1 1 d . . .
H4' H 0.2054 0.3545 0.7640 0.064 Uiso 1 1 calc R . .
O5 O 0.4683(3) 0.3682(2) 0.6298(2) 0.0327(6) Uani 1 1 d . . .
O6 O 0.8887(3) 0.3256(2) 0.6785(2) 0.0351(7) Uani 1 1 d . . .
O7 O 0.6501(4) -0.0248(2) 0.9873(3) 0.0465(8) Uani 1 1 d . . .
O8 O 0.6108(4) 0.1945(3) 1.1525(3) 0.0508(8) Uani 1 1 d . . .
O9 O 0.6657(4) 0.5164(2) 0.6463(3) 0.0425(8) Uani 1 1 d . . .
O10 O 0.7045(4) 0.2922(3) 0.4827(3) 0.0505(8) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.405(5) . ?
C1 C6 1.515(5) . ?
C1 C2 1.535(5) . ?
C1 H1 0.9800 . ?
C2 O2 1.427(4) . ?
C2 C3 1.514(5) . ?
C2 H2 0.9800 . ?
C3 O3 1.442(4) . ?
C3 C4 1.520(5) . ?
C3 H3 0.9800 . ?
C4 O4 1.402(4) . ?
C4 C5 1.489(5) . ?
C4 H4 0.9800 . ?
C5 O5 1.441(4) . ?
C5 C6 1.516(5) . ?
C5 H5 0.9800 . ?
C6 O6 1.428(4) . ?
C6 H6 0.9800 . ?
C7 O7 1.381(5) . ?
C7 O2 1.422(4) . ?
C7 C9 1.530(6) . ?
C7 C10 1.556(6) . ?
C8 O7 1.422(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O8 1.421(6) . ?
C10 O3 1.429(5) . ?
C10 C11 1.494(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O8 1.413(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O5 1.430(5) . ?
C13 O9 1.430(5) . ?
C13 C14 1.510(5) . ?
C13 C16 1.547(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O9 1.427(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O10 1.413(5) . ?
C16 O6 1.438(5) . ?
C16 C17 1.526(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O10 1.427(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 H1' 0.8200 . ?
O4 H4' 0.8200 . ?

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 C1 C6 112.0(3) . . ?
O1 C1 C2 109.0(3) . . ?
C6 C1 C2 106.5(3) . . ?
O1 C1 H1 109.8 . . ?
C6 C1 H1 109.8 . . ?
C2 C1 H1 109.8 . . ?
O2 C2 C3 108.9(3) . . ?
O2 C2 C1 108.9(2) . . ?
C3 C2 C1 112.4(3) . . ?
O2 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
O3 C3 C2 107.9(3) . . ?
O3 C3 C4 108.4(3) . . ?
C2 C3 C4 112.1(3) . . ?
O3 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
O4 C4 C5 110.6(3) . . ?
O4 C4 C3 107.5(3) . . ?
C5 C4 C3 108.1(3) . . ?
O4 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
O5 C5 C4 107.6(3) . . ?
O5 C5 C6 108.4(3) . . ?
C4 C5 C6 113.7(3) . . ?
O5 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
O6 C6 C1 108.8(3) . . ?
O6 C6 C5 108.3(3) . . ?
C1 C6 C5 111.9(3) . . ?
O6 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
O7 C7 O2 110.8(3) . . ?
O7 C7 C9 113.4(4) . . ?
O2 C7 C9 105.3(3) . . ?
O7 C7 C10 105.1(3) . . ?
O2 C7 C10 110.2(3) . . ?
C9 C7 C10 112.1(4) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O7 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 . . ?
O8 C10 O3 109.0(3) . . ?
O8 C10 C11 112.5(4) . . ?
O3 C10 C11 105.3(3) . . ?
O8 C10 C7 104.8(3) . . ?
O3 C10 C7 111.1(3) . . ?
C11 C10 C7 114.1(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O8 C12 H12A 109.5 . . ?
O8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O9 109.6(3) . . ?
O5 C13 C14 104.7(3) . . ?
O9 C13 C14 113.0(3) . . ?
O5 C13 C16 110.8(3) . . ?
O9 C13 C16 106.2(3) . . ?
C14 C13 C16 112.5(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C16 O6 110.1(3) . . ?
O10 C16 C17 114.7(4) . . ?
O6 C16 C17 105.2(3) . . ?
O10 C16 C13 104.7(3) . . ?
O6 C16 C13 110.3(3) . . ?
C17 C16 C13 111.9(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 O1 H1' 109.5 . . ?
C7 O2 C2 112.9(3) . . ?
C10 O3 C3 113.1(3) . . ?
C4 O4 H4' 109.5 . . ?
C13 O5 C5 112.2(3) . . ?
C6 O6 C16 113.4(3) . . ?
C7 O7 C8 115.5(3) . . ?
C12 O8 C10 116.5(3) . . ?
C15 O9 C13 116.6(3) . . ?
C16 O10 C18 116.2(4) . . ?

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
O1 C1 C2 O2 -56.7(4) . . . . ?
C6 C1 C2 O2 -177.7(3) . . . . ?
O1 C1 C2 C3 64.0(4) . . . . ?
C6 C1 C2 C3 -57.0(4) . . . . ?
O2 C2 C3 O3 -61.5(3) . . . . ?
C1 C2 C3 O3 177.8(3) . . . . ?
O2 C2 C3 C4 179.2(3) . . . . ?
C1 C2 C3 C4 58.5(4) . . . . ?
O3 C3 C4 O4 67.0(4) . . . . ?
C2 C3 C4 O4 -174.0(3) . . . . ?
O3 C3 C4 C5 -173.6(3) . . . . ?
C2 C3 C4 C5 -54.6(4) . . . . ?
O4 C4 C5 O5 -67.5(4) . . . . ?
C3 C4 C5 O5 175.2(3) . . . . ?
O4 C4 C5 C6 172.4(3) . . . . ?
C3 C4 C5 C6 55.0(4) . . . . ?
O1 C1 C6 O6 56.8(4) . . . . ?
C2 C1 C6 O6 175.8(3) . . . . ?
O1 C1 C6 C5 -62.9(4) . . . . ?
C2 C1 C6 C5 56.2(4) . . . . ?
O5 C5 C6 O6 61.6(4) . . . . ?
C4 C5 C6 O6 -178.8(3) . . . . ?
O5 C5 C6 C1 -178.5(3) . . . . ?
C4 C5 C6 C1 -58.9(4) . . . . ?
O7 C7 C10 O8 172.0(3) . . . . ?
O2 C7 C10 O8 -68.6(4) . . . . ?
C9 C7 C10 O8 48.4(4) . . . . ?
O7 C7 C10 O3 -70.4(4) . . . . ?
O2 C7 C10 O3 49.0(5) . . . . ?
C9 C7 C10 O3 166.0(4) . . . . ?
O7 C7 C10 C11 48.5(5) . . . . ?
O2 C7 C10 C11 167.9(4) . . . . ?
C9 C7 C10 C11 -75.1(5) . . . . ?
O5 C13 C16 O10 68.8(4) . . . . ?
O9 C13 C16 O10 -172.2(3) . . . . ?
C14 C13 C16 O10 -48.1(4) . . . . ?
O5 C13 C16 O6 -49.6(4) . . . . ?
O9 C13 C16 O6 69.4(4) . . . . ?
C14 C13 C16 O6 -166.5(4) . . . . ?
O5 C13 C16 C17 -166.4(4) . . . . ?
O9 C13 C16 C17 -47.4(5) . . . . ?
C14 C13 C16 C17 76.7(5) . . . . ?
O7 C7 O2 C2 61.3(4) . . . . ?
C9 C7 O2 C2 -175.6(3) . . . . ?
C10 C7 O2 C2 -54.6(4) . . . . ?
C3 C2 O2 C7 61.8(4) . . . . ?
C1 C2 O2 C7 -175.4(3) . . . . ?
O8 C10 O3 C3 61.7(4) . . . . ?
C11 C10 O3 C3 -177.4(4) . . . . ?
C7 C10 O3 C3 -53.3(4) . . . . ?
C2 C3 O3 C10 59.3(4) . . . . ?
C4 C3 O3 C10 -179.1(3) . . . . ?
O9 C13 O5 C5 -61.8(4) . . . . ?
C14 C13 O5 C5 176.6(3) . . . . ?
C16 C13 O5 C5 55.1(4) . . . . ?
C4 C5 O5 C13 175.5(3) . . . . ?
C6 C5 O5 C13 -61.1(4) . . . . ?
C1 C6 O6 C16 178.1(3) . . . . ?
C5 C6 O6 C16 -60.0(4) . . . . ?
O10 C16 O6 C6 -61.2(4) . . . . ?
C17 C16 O6 C6 174.7(3) . . . . ?
C13 C16 O6 C6 53.8(4) . . . . ?
O2 C7 O7 C8 56.5(4) . . . . ?
C9 C7 O7 C8 -61.8(5) . . . . ?
C10 C7 O7 C8 175.5(3) . . . . ?
O3 C10 O8 C12 58.1(4) . . . . ?
C11 C10 O8 C12 -58.3(5) . . . . ?
C7 C10 O8 C12 177.1(3) . . . . ?
O5 C13 O9 C15 -55.7(4) . . . . ?
C14 C13 O9 C15 60.7(4) . . . . ?
C16 C13 O9 C15 -175.5(3) . . . . ?
O6 C16 O10 C18 -62.7(5) . . . . ?
C17 C16 O10 C18 55.8(5) . . . . ?
C13 C16 O10 C18 178.7(4) . . . . ?

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
O1 H1' O4 0.82 2.00 2.784(4) 159.0 1_655
O4 H4' O6 0.82 2.13 2.839(3) 145.4 1_455

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1532605'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H30 F6 O14 S2), C H Cl3'
_chemical_formula_sum            'C41 H61 Cl3 F12 O28 S4'
_chemical_formula_weight         1464.48
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.375(2)
_cell_length_b                   16.966(2)
_cell_length_c                   43.501(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.576(6)
_cell_angle_gamma                90
_cell_volume                     12711(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.95

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.529
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             6032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.390
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            47771
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         0.944
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             10835
_reflns_number_gt                8980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1055P)²+77.1342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10835
_refine_ls_number_parameters     821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2106
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_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
C1A C 0.7848(2) 0.1374(2) 0.13603(9) 0.0209(8) Uani 1 1 d . . . . .
H1A H 0.7399 0.1022 0.1287 0.025 Uiso 1 1 calc R U . . .
C1B C 0.8635(2) 0.5499(2) 0.08241(9) 0.0237(8) Uani 1 1 d . . . . .
H1B H 0.8361 0.4979 0.0803 0.028 Uiso 1 1 calc R U . . .
C2A C 0.7707(2) 0.2206(2) 0.12443(8) 0.0202(8) Uani 1 1 d . . . . .
H2A H 0.8187 0.2528 0.1302 0.024 Uiso 1 1 calc R U . . .
C2B C 0.9429(2) 0.5422(2) 0.10138(9) 0.0228(8) Uani 1 1 d . . . . .
H2B H 0.9710 0.5937 0.1013 0.027 Uiso 1 1 calc R U . . .
C3A C 0.7036(2) 0.2567(2) 0.13881(9) 0.0209(8) Uani 1 1 d . . . . .
H3A H 0.6561 0.2242 0.1327 0.025 Uiso 1 1 calc R U . . .
C3B C 0.9360(2) 0.5187(2) 0.13448(9) 0.0231(8) Uani 1 1 d . . . . .
H3B H 0.9107 0.4657 0.1345 0.028 Uiso 1 1 calc R U . . .
C4A C 0.7195(2) 0.2595(2) 0.17357(9) 0.0223(8) Uani 1 1 d . . . . .
H4A H 0.6747 0.2831 0.1826 0.027 Uiso 1 1 calc R U . . .
C4B C 0.8887(2) 0.5774(2) 0.15021(10) 0.0234(8) Uani 1 1 d . . . . .
H4B H 0.8830 0.5602 0.1718 0.028 Uiso 1 1 calc R U . . .
C5A C 0.7360(2) 0.1768(2) 0.18548(9) 0.0224(8) Uani 1 1 d . . . . .
H5A H 0.6880 0.1442 0.1807 0.027 Uiso 1 1 calc R U . . .
C5B C 0.8103(2) 0.5855(2) 0.13072(9) 0.0230(8) Uani 1 1 d . . . . .
H5B H 0.7831 0.5334 0.1302 0.028 Uiso 1 1 calc R U . . .
C6A C 0.8016(2) 0.1386(2) 0.17106(9) 0.0217(8) Uani 1 1 d . . . . .
H6A H 0.8507 0.1685 0.1774 0.026 Uiso 1 1 calc R U . . .
C6B C 0.8171(2) 0.6101(2) 0.09770(9) 0.0239(8) Uani 1 1 d . . . . .
H6B H 0.8439 0.6624 0.0979 0.029 Uiso 1 1 calc R U . . .
C7A C 0.7388(2) 0.2966(2) 0.07907(9) 0.0239(8) Uani 1 1 d . . . . .
C7B C 1.0634(2) 0.4751(2) 0.10390(11) 0.0285(9) Uani 1 1 d . . . . .
C8A C 0.6720(2) 0.3364(2) 0.09372(9) 0.0252(9) Uani 1 1 d . . . . .
C8B C 1.0600(2) 0.4569(2) 0.13853(10) 0.0277(9) Uani 1 1 d . . . . .
C9A C 0.7714(3) 0.1014(3) 0.23132(10) 0.0310(10) Uani 1 1 d . . . . .
C9B C 0.6892(2) 0.6529(3) 0.12795(10) 0.0274(9) Uani 1 1 d . . . . .
C10A C 0.8320(2) 0.0564(3) 0.21501(9) 0.0301(9) Uani 1 1 d . . . . .
C10B C 0.6949(2) 0.6741(2) 0.09357(10) 0.0286(9) Uani 1 1 d . . . . .
C11A C 0.7210(3) 0.2850(3) 0.04430(9) 0.0325(10) Uani 1 1 d . . . . .
H11A H 0.6753 0.2510 0.0397 0.049 Uiso 1 1 calc R U . . .
H11B H 0.7106 0.3362 0.0342 0.049 Uiso 1 1 calc R U . . .
H11C H 0.7656 0.2602 0.0365 0.049 Uiso 1 1 calc R U . . .
C11B C 1.1002(2) 0.4105(3) 0.08692(12) 0.0344(10) Uani 1 1 d . . . . .
H11D H 1.0707 0.3616 0.0880 0.052 Uiso 1 1 calc R U . . .
H11E H 1.0999 0.4257 0.0652 0.052 Uiso 1 1 calc R U . . .
H11F H 1.1538 0.4023 0.0966 0.052 Uiso 1 1 calc R U . . .
C12A C 0.8759(3) 0.3162(3) 0.07936(11) 0.0362(10) Uani 1 1 d . . . . .
H12A H 0.9176 0.3534 0.0864 0.054 Uiso 1 1 calc R U . . .
H12B H 0.8878 0.2647 0.0890 0.054 Uiso 1 1 calc R U . . .
H12C H 0.8713 0.3110 0.0568 0.054 Uiso 1 1 calc R U . . .
C12B C 1.1115(3) 0.5775(3) 0.07326(12) 0.0415(11) Uani 1 1 d . . . . .
H12D H 1.1393 0.6279 0.0752 0.062 Uiso 1 1 calc R U . . .
H12E H 1.1411 0.5394 0.0625 0.062 Uiso 1 1 calc R U . . .
H12F H 1.0602 0.5852 0.0613 0.062 Uiso 1 1 calc R U . . .
C13A C 0.6608(3) 0.4222(3) 0.08483(11) 0.0355(10) Uani 1 1 d . . . . .
H13A H 0.7084 0.4515 0.0919 0.053 Uiso 1 1 calc R U . . .
H13B H 0.6489 0.4266 0.0622 0.053 Uiso 1 1 calc R U . . .
H13C H 0.6178 0.4440 0.0946 0.053 Uiso 1 1 calc R U . . .
C13B C 1.1385(2) 0.4617(3) 0.15832(12) 0.0372(11) Uani 1 1 d . . . . .
H13D H 1.1594 0.5151 0.1572 0.056 Uiso 1 1 calc R U . . .
H13E H 1.1327 0.4491 0.1799 0.056 Uiso 1 1 calc R U . . .
H13F H 1.1742 0.4239 0.1506 0.056 Uiso 1 1 calc R U . . .
C14A C 0.5361(3) 0.3130(3) 0.09675(11) 0.0439(12) Uani 1 1 d . . . . .
H14A H 0.4935 0.2776 0.0888 0.066 Uiso 1 1 calc R U . . .
H14B H 0.5452 0.3096 0.1194 0.066 Uiso 1 1 calc R U . . .
H14C H 0.5223 0.3673 0.0906 0.066 Uiso 1 1 calc R U . . .
C14B C 1.0145(3) 0.3514(3) 0.16841(12) 0.0427(12) Uani 1 1 d . . . . .
H14D H 0.9900 0.2994 0.1660 0.064 Uiso 1 1 calc R U . . .
H14E H 1.0651 0.3467 0.1812 0.064 Uiso 1 1 calc R U . . .
H14F H 0.9813 0.3872 0.1785 0.064 Uiso 1 1 calc R U . . .
C15A C 0.6383(3) 0.0852(3) 0.23919(14) 0.0516(14) Uani 1 1 d . . . . .
H15A H 0.5940 0.0498 0.2338 0.077 Uiso 1 1 calc R U . . .
H15B H 0.6514 0.0874 0.2618 0.077 Uiso 1 1 calc R U . . .
H15C H 0.6247 0.1382 0.2312 0.077 Uiso 1 1 calc R U . . .
C15B C 0.6529(3) 0.7178(3) 0.14515(11) 0.0402(11) Uani 1 1 d . . . . .
H15D H 0.6849 0.7654 0.1454 0.060 Uiso 1 1 calc R U . . .
H15E H 0.6006 0.7291 0.1347 0.060 Uiso 1 1 calc R U . . .
H15F H 0.6497 0.7008 0.1665 0.060 Uiso 1 1 calc R U . . .
C16A C 0.7992(3) 0.1154(3) 0.26549(10) 0.0443(12) Uani 1 1 d . . . . .
H16A H 0.8469 0.1469 0.2676 0.066 Uiso 1 1 calc R U . . .
H16B H 0.7591 0.1437 0.2749 0.066 Uiso 1 1 calc R U . . .
H16C H 0.8096 0.0647 0.2760 0.066 Uiso 1 1 calc R U . . .
C16B C 0.6350(3) 0.5466(3) 0.15509(12) 0.0450(12) Uani 1 1 d . . . . .
H16D H 0.6056 0.4975 0.1511 0.068 Uiso 1 1 calc R U . . .
H16E H 0.6851 0.5352 0.1674 0.068 Uiso 1 1 calc R U . . .
H16F H 0.6055 0.5831 0.1665 0.068 Uiso 1 1 calc R U . . .
C17A C 0.8364(3) -0.0302(3) 0.22252(11) 0.0443(13) Uani 1 1 d . . . . .
H17A H 0.7857 -0.0546 0.2161 0.067 Uiso 1 1 calc R U . . .
H17B H 0.8756 -0.0551 0.2115 0.067 Uiso 1 1 calc R U . . .
H17C H 0.8506 -0.0372 0.2449 0.067 Uiso 1 1 calc R U . . .
C17B C 0.6175(2) 0.6711(3) 0.07287(11) 0.0376(11) Uani 1 1 d . . . . .
H17D H 0.5960 0.6177 0.0731 0.056 Uiso 1 1 calc R U . . .
H17E H 0.5815 0.7085 0.0805 0.056 Uiso 1 1 calc R U . . .
H17F H 0.6251 0.6851 0.0516 0.056 Uiso 1 1 calc R U . . .
C18A C 0.9678(3) 0.0698(4) 0.20989(12) 0.0580(16) Uani 1 1 d . . . . .
H18A H 1.0134 0.1019 0.2173 0.087 Uiso 1 1 calc R U . . .
H18B H 0.9781 0.0146 0.2157 0.087 Uiso 1 1 calc R U . . .
H18C H 0.9567 0.0741 0.1873 0.087 Uiso 1 1 calc R U . . .
C18B C 0.7443(3) 0.7812(3) 0.06604(13) 0.0484(13) Uani 1 1 d . . . . .
H18D H 0.7697 0.8325 0.0696 0.073 Uiso 1 1 calc R U . . .
H18E H 0.7778 0.7459 0.0559 0.073 Uiso 1 1 calc R U . . .
H18F H 0.6946 0.7878 0.0528 0.073 Uiso 1 1 calc R U . . .
C19A C 0.8859(3) 0.0516(4) 0.07366(12) 0.0510(14) Uani 1 1 d . . . . .
C19B C 0.7698(3) 0.5692(4) 0.00408(13) 0.0562(14) Uani 1 1 d . . . . .
C20A C 0.8500(4) 0.3468(3) 0.23866(13) 0.0570(16) Uani 1 1 d . . . . .
C20B C 0.9159(4) 0.7774(5) 0.1846(3) 0.098(3) Uani 1 1 d . . . . .
O1A O 0.85695(15) 0.10991(16) 0.12481(6) 0.0251(6) Uani 1 1 d . . . . .
O1B O 0.87480(16) 0.58231(17) 0.05188(7) 0.0291(6) Uani 1 1 d . . . . .
O2A O 0.75218(15) 0.21928(16) 0.09171(6) 0.0222(6) Uani 1 1 d . . . . .
O2B O 0.98576(15) 0.48297(15) 0.08779(6) 0.0243(6) Uani 1 1 d . . . . .
O3A O 0.68953(16) 0.33470(16) 0.12700(6) 0.0241(6) Uani 1 1 d . . . . .
O3B O 1.01189(15) 0.51394(16) 0.15134(7) 0.0268(6) Uani 1 1 d . . . . .
O4A O 0.79136(15) 0.30680(16) 0.18203(6) 0.0245(6) Uani 1 1 d . . . . .
O4B O 0.92777(16) 0.65503(16) 0.15030(7) 0.0279(6) Uani 1 1 d . . . . .
O5A O 0.75780(16) 0.17918(17) 0.21810(6) 0.0274(6) Uani 1 1 d . . . . .
O5B O 0.76527(15) 0.64202(16) 0.14470(6) 0.0261(6) Uani 1 1 d . . . . .
O6A O 0.81096(15) 0.05990(16) 0.18195(6) 0.0254(6) Uani 1 1 d . . . . .
O6B O 0.74198(15) 0.61662(16) 0.08056(6) 0.0262(6) Uani 1 1 d . . . . .
O7A O 0.80406(16) 0.34487(16) 0.08794(7) 0.0282(6) Uani 1 1 d . . . . .
O7B O 1.10285(16) 0.54818(17) 0.10340(7) 0.0323(7) Uani 1 1 d . . . . .
O8A O 0.60531(16) 0.29029(17) 0.08423(6) 0.0280(6) Uani 1 1 d . . . . .
O8B O 1.02505(16) 0.38193(16) 0.13861(7) 0.0295(6) Uani 1 1 d . . . . .
O9A O 0.70319(17) 0.05672(18) 0.22570(7) 0.0352(7) Uani 1 1 d . . . . .
O9B O 0.64763(16) 0.58159(18) 0.12621(7) 0.0313(7) Uani 1 1 d . . . . .
O10A O 0.90276(17) 0.0972(2) 0.22354(7) 0.0393(8) Uani 1 1 d . . . . .
O10B O 0.73113(18) 0.74814(17) 0.09494(7) 0.0352(7) Uani 1 1 d . . . . .
O11A O 0.7948(2) -0.0165(2) 0.10891(10) 0.0542(10) Uani 1 1 d . . . . .
O11B O 0.9177(2) 0.5605(3) 0.00132(9) 0.0651(12) Uani 1 1 d . . . . .
O12A O 0.9352(2) -0.0079(2) 0.12751(10) 0.0613(11) Uani 1 1 d . . . . .
O12B O 0.8557(3) 0.4520(2) 0.02714(9) 0.0715(13) Uani 1 1 d . . . . .
O13A O 0.7188(2) 0.4028(2) 0.20912(8) 0.0459(9) Uani 1 1 d . . . . .
O13B O 1.04513(18) 0.7171(2) 0.17389(8) 0.0470(9) Uani 1 1 d . . . . .
O14A O 0.8418(2) 0.4366(2) 0.19025(8) 0.0462(8) Uani 1 1 d . . . . .
O14B O 0.9672(2) 0.6399(3) 0.20679(8) 0.0569(11) Uani 1 1 d . . . . .
F1A F 0.9030(2) -0.0131(3) 0.05884(9) 0.0808(12) Uani 1 1 d . . . . .
F1B F 0.7572(2) 0.5449(3) -0.02539(8) 0.0795(11) Uani 1 1 d . . . . .
F2A F 0.8253(2) 0.0850(2) 0.05743(7) 0.0681(10) Uani 1 1 d . . . . .
F2B F 0.7133(2) 0.5395(3) 0.01872(9) 0.0813(12) Uani 1 1 d . . . . .
F3A F 0.9446(2) 0.1007(3) 0.07524(9) 0.0868(13) Uani 1 1 d . . . . .
F3B F 0.7666(2) 0.6447(2) 0.00475(8) 0.0664(9) Uani 1 1 d . . . . .
F4A F 0.9041(2) 0.2973(2) 0.23261(9) 0.0770(12) Uani 1 1 d . . . . .
F4B F 0.9074(3) 0.8188(3) 0.16006(19) 0.134(3) Uani 1 1 d . . . . .
F5A F 0.8053(3) 0.3116(2) 0.25638(7) 0.0837(13) Uani 1 1 d . . . . .
F5B F 0.8473(2) 0.7587(3) 0.19231(13) 0.1064(18) Uani 1 1 d . . . . .
F6A F 0.8828(3) 0.4082(2) 0.25343(9) 0.0920(15) Uani 1 1 d . . . . .
F6B F 0.9540(3) 0.8168(3) 0.20881(16) 0.141(3) Uani 1 1 d . . . . .
S1A S 0.86567(6) 0.02507(7) 0.11228(3) 0.0348(3) Uani 1 1 d . . . . .
S1B S 0.86387(8) 0.53276(8) 0.02126(3) 0.0466(3) Uani 1 1 d . . . . .
S2A S 0.79327(6) 0.38163(6) 0.20233(2) 0.0297(3) Uani 1 1 d . . . . .
S2B S 0.97293(6) 0.68900(7) 0.18057(3) 0.0377(3) Uani 1 1 d . . . . .
C1 C 1.0077(3) 0.7986(4) 0.01442(11) 0.0521(15) Uani 1 1 d . . . . .
H1 H 1.0413 0.7887 0.0345 0.062 Uiso 1 1 calc R U . A 1
Cl1 Cl 1.0338(3) 0.7337(5) -0.01300(16) 0.0849(19) Uani 0.78(2) 1 d . . P B 1
Cl2 Cl 1.0230(3) 0.8971(4) 0.00248(9) 0.0787(15) Uani 0.78(2) 1 d . . P B 1
Cl3 Cl 0.9103(3) 0.7834(5) 0.01972(16) 0.0715(14) Uani 0.78(2) 1 d . . P B 1
Cl1' Cl 1.0337(12) 0.7131(18) -0.0051(6) 0.095(7) Uani 0.22(2) 1 d . . P B 2
Cl2' Cl 1.0341(17) 0.874(2) -0.0004(8) 0.173(14) Uani 0.22(2) 1 d . . P B 2
Cl3' Cl 0.9120(15) 0.809(3) 0.0163(7) 0.114(11) Uani 0.22(2) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A O1A 1.479(4) . ?
C1A C2A 1.509(5) . ?
C1A C6A 1.513(5) . ?
C1A H1A 1.0000 . ?
C1B O1B 1.474(5) . ?
C1B C6B 1.509(5) . ?
C1B C2B 1.517(5) . ?
C1B H1B 1.0000 . ?
C2A O2A 1.417(4) . ?
C2A C3A 1.523(5) . ?
C2A H2A 1.0000 . ?
C2B O2B 1.425(4) . ?
C2B C3B 1.514(6) . ?
C2B H2B 1.0000 . ?
C3A O3A 1.428(5) . ?
C3A C4A 1.502(5) . ?
C3A H3A 1.0000 . ?
C3B O3B 1.424(5) . ?
C3B C4B 1.512(5) . ?
C3B H3B 1.0000 . ?
C4A O4A 1.489(4) . ?
C4A C5A 1.509(5) . ?
C4A H4A 1.0000 . ?
C4B O4B 1.482(5) . ?
C4B C5B 1.513(5) . ?
C4B H4B 1.0000 . ?
C5A O5A 1.420(5) . ?
C5A C6A 1.518(5) . ?
C5A H5A 1.0000 . ?
C5B O5B 1.424(5) . ?
C5B C6B 1.516(6) . ?
C5B H5B 1.0000 . ?
C6A O6A 1.419(5) . ?
C6A H6A 1.0000 . ?
C6B O6B 1.420(5) . ?
C6B H6B 1.0000 . ?
C7A O7A 1.411(5) . ?
C7A O2A 1.429(5) . ?
C7A C11A 1.516(5) . ?
C7A C8A 1.551(6) . ?
C7B O7B 1.419(5) . ?
C7B O2B 1.442(5) . ?
C7B C11B 1.510(6) . ?
C7B C8B 1.547(6) . ?
C8A O8A 1.414(5) . ?
C8A O3A 1.440(5) . ?
C8A C13A 1.512(6) . ?
C8B O8B 1.409(5) . ?
C8B O3B 1.438(5) . ?
C8B C13B 1.517(6) . ?
C9A O9A 1.401(5) . ?
C9A O5A 1.447(5) . ?
C9A C16A 1.520(6) . ?
C9A C10A 1.546(6) . ?
C9B O9B 1.406(5) . ?
C9B O5B 1.435(5) . ?
C9B C15B 1.514(6) . ?
C9B C10B 1.554(6) . ?
C10A O10A 1.417(5) . ?
C10A O6A 1.438(5) . ?
C10A C17A 1.504(7) . ?
C10B O10B 1.403(5) . ?
C10B O6B 1.436(5) . ?
C10B C17B 1.517(6) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12A O7A 1.434(5) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C12B O7B 1.429(6) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14A O8A 1.437(5) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C14B O8B 1.430(6) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15A O9A 1.423(5) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16B O9B 1.433(6) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18A O10A 1.421(6) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18B O10B 1.422(6) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19A F3A 1.313(7) . ?
C19A F2A 1.315(7) . ?
C19A F1A 1.326(6) . ?
C19A S1A 1.817(6) . ?
C19B F3B 1.283(7) . ?
C19B F1B 1.337(7) . ?
C19B F2B 1.338(7) . ?
C19B S1B 1.813(6) . ?
C20A F5A 1.308(8) . ?
C20A F4A 1.313(7) . ?
C20A F6A 1.314(6) . ?
C20A S2A 1.846(5) . ?
C20B F4B 1.270(13) . ?
C20B F5B 1.319(9) . ?
C20B F6B 1.346(9) . ?
C20B S2B 1.818(7) . ?
O1A S1A 1.554(3) . ?
O1B S1B 1.565(3) . ?
O4A S2A 1.544(3) . ?
O4B S2B 1.552(3) . ?
O11A S1A 1.409(4) . ?
O11B S1B 1.436(4) . ?
O12A S1A 1.414(4) . ?
O12B S1B 1.405(4) . ?
O13A S2A 1.411(3) . ?
O13B S2B 1.408(3) . ?
O14A S2A 1.405(4) . ?
O14B S2B 1.427(4) . ?
C1 Cl2' 1.52(3) . ?
C1 Cl3' 1.69(3) . ?
C1 Cl1 1.727(7) . ?
C1 Cl3 1.757(7) . ?
C1 Cl1' 1.77(2) . ?
C1 Cl2 1.780(9) . ?
C1 H1 1.0000 . ?

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
O1A C1A C2A 107.0(3) . . ?
O1A C1A C6A 106.1(3) . . ?
C2A C1A C6A 109.0(3) . . ?
O1A C1A H1A 111.5 . . ?
C2A C1A H1A 111.5 . . ?
C6A C1A H1A 111.5 . . ?
O1B C1B C6B 106.6(3) . . ?
O1B C1B C2B 107.6(3) . . ?
C6B C1B C2B 108.5(3) . . ?
O1B C1B H1B 111.3 . . ?
C6B C1B H1B 111.3 . . ?
C2B C1B H1B 111.3 . . ?
O2A C2A C1A 109.0(3) . . ?
O2A C2A C3A 109.5(3) . . ?
C1A C2A C3A 109.8(3) . . ?
O2A C2A H2A 109.5 . . ?
C1A C2A H2A 109.5 . . ?
C3A C2A H2A 109.5 . . ?
O2B C2B C3B 108.6(3) . . ?
O2B C2B C1B 108.8(3) . . ?
C3B C2B C1B 111.1(3) . . ?
O2B C2B H2B 109.5 . . ?
C3B C2B H2B 109.5 . . ?
C1B C2B H2B 109.5 . . ?
O3A C3A C4A 109.5(3) . . ?
O3A C3A C2A 109.2(3) . . ?
C4A C3A C2A 112.2(3) . . ?
O3A C3A H3A 108.6 . . ?
C4A C3A H3A 108.6 . . ?
C2A C3A H3A 108.6 . . ?
O3B C3B C4B 109.1(3) . . ?
O3B C3B C2B 108.7(3) . . ?
C4B C3B C2B 111.8(3) . . ?
O3B C3B H3B 109.1 . . ?
C4B C3B H3B 109.1 . . ?
C2B C3B H3B 109.1 . . ?
O4A C4A C3A 107.6(3) . . ?
O4A C4A C5A 107.5(3) . . ?
C3A C4A C5A 108.5(3) . . ?
O4A C4A H4A 111.0 . . ?
C3A C4A H4A 111.0 . . ?
C5A C4A H4A 111.0 . . ?
O4B C4B C3B 108.1(3) . . ?
O4B C4B C5B 107.5(3) . . ?
C3B C4B C5B 108.0(3) . . ?
O4B C4B H4B 111.0 . . ?
C3B C4B H4B 111.0 . . ?
C5B C4B H4B 111.0 . . ?
O5A C5A C4A 109.3(3) . . ?
O5A C5A C6A 108.0(3) . . ?
C4A C5A C6A 112.0(3) . . ?
O5A C5A H5A 109.2 . . ?
C4A C5A H5A 109.2 . . ?
C6A C5A H5A 109.2 . . ?
O5B C5B C4B 109.0(3) . . ?
O5B C5B C6B 109.6(3) . . ?
C4B C5B C6B 112.2(3) . . ?
O5B C5B H5B 108.6 . . ?
C4B C5B H5B 108.6 . . ?
C6B C5B H5B 108.6 . . ?
O6A C6A C1A 108.8(3) . . ?
O6A C6A C5A 108.9(3) . . ?
C1A C6A C5A 111.5(3) . . ?
O6A C6A H6A 109.2 . . ?
C1A C6A H6A 109.2 . . ?
C5A C6A H6A 109.2 . . ?
O6B C6B C1B 109.2(3) . . ?
O6B C6B C5B 109.7(3) . . ?
C1B C6B C5B 110.1(3) . . ?
O6B C6B H6B 109.3 . . ?
C1B C6B H6B 109.3 . . ?
C5B C6B H6B 109.3 . . ?
O7A C7A O2A 110.1(3) . . ?
O7A C7A C11A 113.5(3) . . ?
O2A C7A C11A 105.4(3) . . ?
O7A C7A C8A 104.6(3) . . ?
O2A C7A C8A 109.5(3) . . ?
C11A C7A C8A 113.6(3) . . ?
O7B C7B O2B 109.5(3) . . ?
O7B C7B C11B 113.0(3) . . ?
O2B C7B C11B 105.0(3) . . ?
O7B C7B C8B 105.7(3) . . ?
O2B C7B C8B 109.8(3) . . ?
C11B C7B C8B 113.9(4) . . ?
O8A C8A O3A 109.8(3) . . ?
O8A C8A C13A 112.6(3) . . ?
O3A C8A C13A 106.2(3) . . ?
O8A C8A C7A 105.6(3) . . ?
O3A C8A C7A 109.5(3) . . ?
C13A C8A C7A 113.1(3) . . ?
O8B C8B O3B 109.5(3) . . ?
O8B C8B C13B 113.7(3) . . ?
O3B C8B C13B 105.6(3) . . ?
O8B C8B C7B 104.7(3) . . ?
O3B C8B C7B 110.0(3) . . ?
C13B C8B C7B 113.3(3) . . ?
O9A C9A O5A 109.5(3) . . ?
O9A C9A C16A 114.1(4) . . ?
O5A C9A C16A 105.1(4) . . ?
O9A C9A C10A 105.3(4) . . ?
O5A C9A C10A 110.7(3) . . ?
C16A C9A C10A 112.2(4) . . ?
O9B C9B O5B 110.4(3) . . ?
O9B C9B C15B 114.1(4) . . ?
O5B C9B C15B 105.0(3) . . ?
O9B C9B C10B 104.2(3) . . ?
O5B C9B C10B 110.3(3) . . ?
C15B C9B C10B 113.0(4) . . ?
O10A C10A O6A 109.8(3) . . ?
O10A C10A C17A 113.7(4) . . ?
O6A C10A C17A 104.9(4) . . ?
O10A C10A C9A 105.0(4) . . ?
O6A C10A C9A 109.9(3) . . ?
C17A C10A C9A 113.6(4) . . ?
O10B C10B O6B 110.4(3) . . ?
O10B C10B C17B 114.4(4) . . ?
O6B C10B C17B 104.5(3) . . ?
O10B C10B C9B 104.5(3) . . ?
O6B C10B C9B 109.5(3) . . ?
C17B C10B C9B 113.5(3) . . ?
C7A C11A H11A 109.5 . . ?
C7A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C7A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C7B C11B H11D 109.5 . . ?
C7B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C7B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
O7A C12A H12A 109.5 . . ?
O7A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O7A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O7B C12B H12D 109.5 . . ?
O7B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
O7B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C8A C13A H13A 109.5 . . ?
C8A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C8A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C8B C13B H13D 109.5 . . ?
C8B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C8B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O8A C14A H14A 109.5 . . ?
O8A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
O8A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O8B C14B H14D 109.5 . . ?
O8B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
O8B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O9A C15A H15A 109.5 . . ?
O9A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O9A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C9B C15B H15D 109.5 . . ?
C9B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C9B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C9A C16A H16A 109.5 . . ?
C9A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C9A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
O9B C16B H16D 109.5 . . ?
O9B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
O9B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C10A C17A H17A 109.5 . . ?
C10A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C10A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C10B C17B H17D 109.5 . . ?
C10B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C10B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O10A C18A H18A 109.5 . . ?
O10A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
O10A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O10B C18B H18D 109.5 . . ?
O10B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
O10B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
F3A C19A F2A 108.3(5) . . ?
F3A C19A F1A 109.1(4) . . ?
F2A C19A F1A 108.1(4) . . ?
F3A C19A S1A 110.6(4) . . ?
F2A C19A S1A 111.4(4) . . ?
F1A C19A S1A 109.2(4) . . ?
F3B C19B F1B 109.2(5) . . ?
F3B C19B F2B 109.2(5) . . ?
F1B C19B F2B 107.6(5) . . ?
F3B C19B S1B 111.8(4) . . ?
F1B C19B S1B 108.4(4) . . ?
F2B C19B S1B 110.7(4) . . ?
F5A C20A F4A 108.8(5) . . ?
F5A C20A F6A 109.1(5) . . ?
F4A C20A F6A 109.2(6) . . ?
F5A C20A S2A 111.0(4) . . ?
F4A C20A S2A 110.4(4) . . ?
F6A C20A S2A 108.2(4) . . ?
F4B C20B F5B 109.7(8) . . ?
F4B C20B F6B 112.0(8) . . ?
F5B C20B F6B 106.7(8) . . ?
F4B C20B S2B 112.4(6) . . ?
F5B C20B S2B 110.3(6) . . ?
F6B C20B S2B 105.5(6) . . ?
C1A O1A S1A 122.3(2) . . ?
C1B O1B S1B 123.4(3) . . ?
C2A O2A C7A 112.1(3) . . ?
C2B O2B C7B 111.7(3) . . ?
C3A O3A C8A 112.5(3) . . ?
C3B O3B C8B 112.6(3) . . ?
C4A O4A S2A 122.6(2) . . ?
C4B O4B S2B 120.9(3) . . ?
C5A O5A C9A 112.3(3) . . ?
C5B O5B C9B 113.0(3) . . ?
C6A O6A C10A 112.1(3) . . ?
C6B O6B C10B 112.2(3) . . ?
C7A O7A C12A 115.3(3) . . ?
C7B O7B C12B 115.3(3) . . ?
C8A O8A C14A 115.9(3) . . ?
C8B O8B C14B 115.8(3) . . ?
C9A O9A C15A 116.3(4) . . ?
C9B O9B C16B 116.5(3) . . ?
C10A O10A C18A 116.2(4) . . ?
C10B O10B C18B 116.0(4) . . ?
O11A S1A O12A 122.1(3) . . ?
O11A S1A O1A 112.05(18) . . ?
O12A S1A O1A 108.6(2) . . ?
O11A S1A C19A 107.5(3) . . ?
O12A S1A C19A 105.9(3) . . ?
O1A S1A C19A 97.8(2) . . ?
O12B S1B O11B 121.3(3) . . ?
O12B S1B O1B 111.9(2) . . ?
O11B S1B O1B 108.8(2) . . ?
O12B S1B C19B 107.5(3) . . ?
O11B S1B C19B 105.2(3) . . ?
O1B S1B C19B 99.7(2) . . ?
O14A S2A O13A 121.4(2) . . ?
O14A S2A O4A 107.52(18) . . ?
O13A S2A O4A 112.19(18) . . ?
O14A S2A C20A 104.7(3) . . ?
O13A S2A C20A 107.6(3) . . ?
O4A S2A C20A 101.3(2) . . ?
O13B S2B O14B 121.4(2) . . ?
O13B S2B O4B 108.39(19) . . ?
O14B S2B O4B 112.36(19) . . ?
O13B S2B C20B 104.6(3) . . ?
O14B S2B C20B 108.0(4) . . ?
O4B S2B C20B 99.6(3) . . ?
Cl2' C1 Cl3' 106.5(15) . . ?
Cl1 C1 Cl3 110.0(5) . . ?
Cl2' C1 Cl1' 111.8(17) . . ?
Cl3' C1 Cl1' 115.3(16) . . ?
Cl1 C1 Cl2 109.5(4) . . ?
Cl3 C1 Cl2 111.0(4) . . ?
Cl1 C1 H1 108.7 . . ?
Cl3 C1 H1 108.7 . . ?
Cl2 C1 H1 108.7 . . ?

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
O1A C1A C2A O2A 67.8(4) . . . . ?
C6A C1A C2A O2A -177.8(3) . . . . ?
O1A C1A C2A C3A -172.2(3) . . . . ?
C6A C1A C2A C3A -57.9(4) . . . . ?
O1B C1B C2B O2B -67.4(4) . . . . ?
C6B C1B C2B O2B 177.5(3) . . . . ?
O1B C1B C2B C3B 173.1(3) . . . . ?
C6B C1B C2B C3B 58.0(4) . . . . ?
O2A C2A C3A O3A -58.8(4) . . . . ?
C1A C2A C3A O3A -178.4(3) . . . . ?
O2A C2A C3A C4A 179.7(3) . . . . ?
C1A C2A C3A C4A 60.0(4) . . . . ?
O2B C2B C3B O3B 61.6(4) . . . . ?
C1B C2B C3B O3B -178.8(3) . . . . ?
O2B C2B C3B C4B -178.0(3) . . . . ?
C1B C2B C3B C4B -58.4(4) . . . . ?
O3A C3A C4A O4A -62.7(4) . . . . ?
C2A C3A C4A O4A 58.7(4) . . . . ?
O3A C3A C4A C5A -178.7(3) . . . . ?
C2A C3A C4A C5A -57.3(4) . . . . ?
O3B C3B C4B O4B 60.3(4) . . . . ?
C2B C3B C4B O4B -60.0(4) . . . . ?
O3B C3B C4B C5B 176.2(3) . . . . ?
C2B C3B C4B C5B 56.0(4) . . . . ?
O4A C4A C5A O5A 58.8(4) . . . . ?
C3A C4A C5A O5A 174.9(3) . . . . ?
O4A C4A C5A C6A -60.8(4) . . . . ?
C3A C4A C5A C6A 55.3(4) . . . . ?
O4B C4B C5B O5B -62.2(4) . . . . ?
C3B C4B C5B O5B -178.6(3) . . . . ?
O4B C4B C5B C6B 59.4(4) . . . . ?
C3B C4B C5B C6B -57.0(4) . . . . ?
O1A C1A C6A O6A -68.0(4) . . . . ?
C2A C1A C6A O6A 177.1(3) . . . . ?
O1A C1A C6A C5A 171.9(3) . . . . ?
C2A C1A C6A C5A 57.0(4) . . . . ?
O5A C5A C6A O6A 62.9(4) . . . . ?
C4A C5A C6A O6A -176.8(3) . . . . ?
O5A C5A C6A C1A -177.1(3) . . . . ?
C4A C5A C6A C1A -56.8(4) . . . . ?
O1B C1B C6B O6B 65.6(4) . . . . ?
C2B C1B C6B O6B -178.7(3) . . . . ?
O1B C1B C6B C5B -173.9(3) . . . . ?
C2B C1B C6B C5B -58.2(4) . . . . ?
O5B C5B C6B O6B -58.8(4) . . . . ?
C4B C5B C6B O6B 179.9(3) . . . . ?
O5B C5B C6B C1B -179.0(3) . . . . ?
C4B C5B C6B C1B 59.7(4) . . . . ?
O7A C7A C8A O8A 178.1(3) . . . . ?
O2A C7A C8A O8A -63.9(4) . . . . ?
C11A C7A C8A O8A 53.7(4) . . . . ?
O7A C7A C8A O3A -63.7(4) . . . . ?
O2A C7A C8A O3A 54.3(4) . . . . ?
C11A C7A C8A O3A 171.9(3) . . . . ?
O7A C7A C8A C13A 54.5(4) . . . . ?
O2A C7A C8A C13A 172.5(3) . . . . ?
C11A C7A C8A C13A -69.9(4) . . . . ?
O7B C7B C8B O8B -176.4(3) . . . . ?
O2B C7B C8B O8B 65.6(4) . . . . ?
C11B C7B C8B O8B -51.8(4) . . . . ?
O7B C7B C8B O3B 66.0(4) . . . . ?
O2B C7B C8B O3B -52.1(4) . . . . ?
C11B C7B C8B O3B -169.4(3) . . . . ?
O7B C7B C8B C13B -51.9(4) . . . . ?
O2B C7B C8B C13B -170.0(3) . . . . ?
C11B C7B C8B C13B 72.7(5) . . . . ?
O9A C9A C10A O10A -174.0(3) . . . . ?
O5A C9A C10A O10A 67.8(4) . . . . ?
C16A C9A C10A O10A -49.3(5) . . . . ?
O9A C9A C10A O6A 68.0(4) . . . . ?
O5A C9A C10A O6A -50.3(5) . . . . ?
C16A C9A C10A O6A -167.3(4) . . . . ?
O9A C9A C10A C17A -49.1(5) . . . . ?
O5A C9A C10A C17A -167.4(4) . . . . ?
C16A C9A C10A C17A 75.6(5) . . . . ?
O9B C9B C10B O10B 175.7(3) . . . . ?
O5B C9B C10B O10B -65.8(4) . . . . ?
C15B C9B C10B O10B 51.3(4) . . . . ?
O9B C9B C10B O6B -66.0(4) . . . . ?
O5B C9B C10B O6B 52.5(4) . . . . ?
C15B C9B C10B O6B 169.7(3) . . . . ?
O9B C9B C10B C17B 50.4(4) . . . . ?
O5B C9B C10B C17B 168.9(3) . . . . ?
C15B C9B C10B C17B -74.0(5) . . . . ?
C2A C1A O1A S1A -139.3(3) . . . . ?
C6A C1A O1A S1A 104.5(3) . . . . ?
C6B C1B O1B S1B -135.4(3) . . . . ?
C2B C1B O1B S1B 108.3(3) . . . . ?
C1A C2A O2A C7A -179.4(3) . . . . ?
C3A C2A O2A C7A 60.5(4) . . . . ?
O7A C7A O2A C2A 56.4(4) . . . . ?
C11A C7A O2A C2A 179.2(3) . . . . ?
C8A C7A O2A C2A -58.1(4) . . . . ?
C3B C2B O2B C7B -61.6(4) . . . . ?
C1B C2B O2B C7B 177.4(3) . . . . ?
O7B C7B O2B C2B -58.7(4) . . . . ?
C11B C7B O2B C2B 179.7(3) . . . . ?
C8B C7B O2B C2B 56.9(4) . . . . ?
C4A C3A O3A C8A -178.6(3) . . . . ?
C2A C3A O3A C8A 58.2(4) . . . . ?
O8A C8A O3A C3A 59.4(4) . . . . ?
C13A C8A O3A C3A -178.5(3) . . . . ?
C7A C8A O3A C3A -56.1(4) . . . . ?
C4B C3B O3B C8B 177.8(3) . . . . ?
C2B C3B O3B C8B -60.1(4) . . . . ?
O8B C8B O3B C3B -59.2(4) . . . . ?
C13B C8B O3B C3B 178.0(3) . . . . ?
C7B C8B O3B C3B 55.4(4) . . . . ?
C3A C4A O4A S2A 122.0(3) . . . . ?
C5A C4A O4A S2A -121.2(3) . . . . ?
C3B C4B O4B S2B -106.0(3) . . . . ?
C5B C4B O4B S2B 137.6(3) . . . . ?
C4A C5A O5A C9A 177.6(3) . . . . ?
C6A C5A O5A C9A -60.4(4) . . . . ?
O9A C9A O5A C5A -60.8(4) . . . . ?
C16A C9A O5A C5A 176.2(3) . . . . ?
C10A C9A O5A C5A 54.9(4) . . . . ?
C4B C5B O5B C9B -179.2(3) . . . . ?
C6B C5B O5B C9B 57.6(4) . . . . ?
O9B C9B O5B C5B 59.9(4) . . . . ?
C15B C9B O5B C5B -176.7(3) . . . . ?
C10B C9B O5B C5B -54.7(4) . . . . ?
C1A C6A O6A C10A 176.3(3) . . . . ?
C5A C6A O6A C10A -62.0(4) . . . . ?
O10A C10A O6A C6A -59.6(4) . . . . ?
C17A C10A O6A C6A 177.9(3) . . . . ?
C9A C10A O6A C6A 55.4(4) . . . . ?
C1B C6B O6B C10B -179.1(3) . . . . ?
C5B C6B O6B C10B 60.2(4) . . . . ?
O10B C10B O6B C6B 57.9(4) . . . . ?
C17B C10B O6B C6B -178.7(3) . . . . ?
C9B C10B O6B C6B -56.7(4) . . . . ?
O2A C7A O7A C12A 57.1(4) . . . . ?
C11A C7A O7A C12A -60.8(5) . . . . ?
C8A C7A O7A C12A 174.7(3) . . . . ?
O2B C7B O7B C12B -60.8(4) . . . . ?
C11B C7B O7B C12B 55.9(5) . . . . ?
C8B C7B O7B C12B -178.9(3) . . . . ?
O3A C8A O8A C14A 58.1(4) . . . . ?
C13A C8A O8A C14A -60.0(5) . . . . ?
C7A C8A O8A C14A 176.1(3) . . . . ?
O3B C8B O8B C14B -61.6(4) . . . . ?
C13B C8B O8B C14B 56.3(5) . . . . ?
C7B C8B O8B C14B -179.6(3) . . . . ?
O5A C9A O9A C15A -62.5(5) . . . . ?
C16A C9A O9A C15A 55.0(5) . . . . ?
C10A C9A O9A C15A 178.5(4) . . . . ?
O5B C9B O9B C16B 60.2(4) . . . . ?
C15B C9B O9B C16B -57.7(5) . . . . ?
C10B C9B O9B C16B 178.6(3) . . . . ?
O6A C10A O10A C18A -58.3(5) . . . . ?
C17A C10A O10A C18A 58.8(5) . . . . ?
C9A C10A O10A C18A -176.4(4) . . . . ?
O6B C10B O10B C18B 61.6(4) . . . . ?
C17B C10B O10B C18B -55.9(5) . . . . ?
C9B C10B O10B C18B 179.3(3) . . . . ?
C1A O1A S1A O11A 8.5(4) . . . . ?
C1A O1A S1A O12A -129.4(3) . . . . ?
C1A O1A S1A C19A 120.9(3) . . . . ?
F3A C19A S1A O11A 170.2(4) . . . . ?
F2A C19A S1A O11A 49.6(5) . . . . ?
F1A C19A S1A O11A -69.7(4) . . . . ?
F3A C19A S1A O12A -57.8(5) . . . . ?
F2A C19A S1A O12A -178.4(4) . . . . ?
F1A C19A S1A O12A 62.3(4) . . . . ?
F3A C19A S1A O1A 54.1(4) . . . . ?
F2A C19A S1A O1A -66.5(4) . . . . ?
F1A C19A S1A O1A 174.2(4) . . . . ?
C1B O1B S1B O12B -10.4(4) . . . . ?
C1B O1B S1B O11B -147.1(3) . . . . ?
C1B O1B S1B C19B 103.1(3) . . . . ?
F3B C19B S1B O12B 164.3(4) . . . . ?
F1B C19B S1B O12B -75.3(5) . . . . ?
F2B C19B S1B O12B 42.4(5) . . . . ?
F3B C19B S1B O11B -65.1(5) . . . . ?
F1B C19B S1B O11B 55.2(5) . . . . ?
F2B C19B S1B O11B 172.9(4) . . . . ?
F3B C19B S1B O1B 47.5(4) . . . . ?
F1B C19B S1B O1B 167.9(4) . . . . ?
F2B C19B S1B O1B -74.4(4) . . . . ?
C4A O4A S2A O14A -141.4(3) . . . . ?
C4A O4A S2A O13A -5.5(3) . . . . ?
C4A O4A S2A C20A 109.0(3) . . . . ?
F5A C20A S2A O14A 163.2(4) . . . . ?
F4A C20A S2A O14A -76.0(5) . . . . ?
F6A C20A S2A O14A 43.5(5) . . . . ?
F5A C20A S2A O13A 32.7(4) . . . . ?
F4A C20A S2A O13A 153.5(4) . . . . ?
F6A C20A S2A O13A -86.9(5) . . . . ?
F5A C20A S2A O4A -85.1(4) . . . . ?
F4A C20A S2A O4A 35.7(5) . . . . ?
F6A C20A S2A O4A 155.2(5) . . . . ?
C4B O4B S2B O13B 133.4(3) . . . . ?
C4B O4B S2B O14B -3.5(3) . . . . ?
C4B O4B S2B C20B -117.6(4) . . . . ?
F4B C20B S2B O13B 60.0(6) . . . . ?
F5B C20B S2B O13B -177.2(6) . . . . ?
F6B C20B S2B O13B -62.3(8) . . . . ?
F4B C20B S2B O14B -169.4(5) . . . . ?
F5B C20B S2B O14B -46.6(8) . . . . ?
F6B C20B S2B O14B 68.3(7) . . . . ?
F4B C20B S2B O4B -52.0(6) . . . . ?
F5B C20B S2B O4B 70.8(7) . . . . ?
F6B C20B S2B O4B -174.3(7) . . . . ?

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
C4A H4A O13B 1.00 2.50 3.115(5) 119.6 3_445
C4B H4B O14A 1.00 2.39 3.127(5) 130.0 .
C12A H12A O2B 0.98 2.49 3.405(5) 154.8 .
C12A H12C Cl1 0.98 2.78 3.565(7) 137.2 5_765
C12B H12D O2A 0.98 2.53 3.448(5) 156.1 3
C15A H15A F6A 0.98 2.49 3.048(7) 116.2 4_645
C17A H17B F6B 0.98 2.58 3.405(6) 142.4 1_545
C17B H17F Cl3' 0.98 2.94 3.86(3) 156.4 7_665
C1 H1 O8A 1.00 2.30 3.280(6) 167.4 3

_refine_diff_density_max         3.340
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3

