# Electronic Supplementary Material (ESI) for Energy & Environmental Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_X16194
_database_code_depnum_ccdc_archive 'CCDC 1590310'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 F5 N2 Na O7 S2'
_chemical_formula_weight         508.41

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'
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'
Na Na 0.0362 0.0249 '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                   7.9576(11)
_cell_length_b                   28.725(4)
_cell_length_c                   8.9535(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.063(3)
_cell_angle_gamma                90
_cell_volume                     2046.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4442
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.367
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            36594
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.418
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4875
_reflns_number_gt                3546
_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 v2011.4.0 (Bruker-AXS, 2015)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Small crystals, weak diffraction. There is a possible whole molecule
 disorder, but to model this would not be reasonable because of the 
 restraints needed and quality of the so obtained structure. The 
 disorder of the piperidine part of the structure was set to a ratio
 of 50:50. The position has to be alternating from one molecule to 
 the next in the crystal.
  
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+10.1930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4875
_refine_ls_number_parameters     333
_refine_ls_number_restraints     662
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.136
_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
S1 S 0.52970(14) 0.29243(4) 0.84448(12) 0.0231(2) Uani 1 1 d . U . . .
Na1 Na 0.3865(2) 0.27491(6) 0.47647(19) 0.0251(4) Uani 1 1 d . U . . .
S2 S 0.18809(14) 0.30926(4) 0.80929(13) 0.0259(3) Uani 1 1 d . U . . .
F1 F 0.6418(5) 0.45861(11) 0.9992(3) 0.0521(9) Uani 1 1 d . U . . .
F2 F 0.7064(3) 0.42332(9) 0.4885(3) 0.0300(6) Uani 1 1 d . U . . .
F3 F -0.0065(4) 0.38159(12) 0.7933(4) 0.0461(8) Uani 1 1 d . U . . .
F4 F 0.0941(5) 0.36837(16) 1.0131(4) 0.0733(13) Uani 1 1 d . U . . .
F5 F 0.2499(4) 0.39871(11) 0.8459(4) 0.0512(9) Uani 1 1 d . U . . .
N1 N 0.7288(5) 0.48919(15) 0.7058(5) 0.0362(10) Uani 1 1 d D U . . .
O1 O 0.5507(4) 0.37013(13) 1.0545(3) 0.0353(8) Uani 1 1 d . U . . .
O2 O 0.6256(4) 0.33482(11) 0.5317(3) 0.0241(7) Uani 1 1 d . U . . .
O3 O 0.5301(4) 0.26393(11) 0.7114(3) 0.0233(7) Uani 1 1 d . U . . .
O4 O 0.6375(4) 0.27635(12) 0.9656(3) 0.0269(7) Uani 1 1 d . U . . .
O5 O 0.2188(4) 0.31518(12) 0.6528(3) 0.0270(7) Uani 1 1 d . U . . .
O6 O 0.0451(4) 0.28190(14) 0.8510(4) 0.0432(10) Uani 1 1 d . U . . .
O7 O 0.3019(4) 0.30416(13) 0.2486(4) 0.0314(8) Uani 1 1 d D U . . .
H7O H 0.349(6) 0.310(2) 0.168(4) 0.047 Uiso 1 1 d D U . . .
H7P H 0.208(4) 0.2914(19) 0.229(6) 0.047 Uiso 1 1 d D U . . .
N2 N 0.3436(5) 0.29678(15) 0.9106(4) 0.0280(9) Uani 1 1 d . U . . .
C1 C 0.6789(6) 0.44437(17) 0.7414(6) 0.0314(10) Uani 1 1 d . U . . .
C2 C 0.6403(6) 0.42823(18) 0.8834(5) 0.0327(10) Uani 1 1 d . U . . .
C3 C 0.6010(6) 0.38276(18) 0.9140(5) 0.0285(10) Uani 1 1 d . U . . .
C4 C 0.5919(5) 0.34974(16) 0.7990(5) 0.0223(9) Uani 1 1 d . U . . .
C5 C 0.6267(5) 0.36410(16) 0.6533(5) 0.0227(9) Uani 1 1 d . U . . .
C6 C 0.6692(6) 0.41053(17) 0.6295(5) 0.0279(10) Uani 1 1 d . U . . .
C7 C 0.6868(7) 0.3685(2) 1.1635(6) 0.0453(15) Uani 1 1 d . U . . .
H7A H 0.7692 0.3451 1.1335 0.068 Uiso 1 1 calc R U . . .
H7B H 0.6424 0.3602 1.2614 0.068 Uiso 1 1 calc R U . . .
H7C H 0.7412 0.3990 1.1697 0.068 Uiso 1 1 calc R U . . .
C8 C 0.7925(6) 0.31621(18) 0.5031(5) 0.0301(10) Uani 1 1 d . U . . .
H8A H 0.7878 0.2966 0.4136 0.045 Uiso 1 1 calc R U . . .
H8B H 0.8309 0.2976 0.5888 0.045 Uiso 1 1 calc R U . . .
H8C H 0.8710 0.3420 0.4875 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1299(6) 0.3680(2) 0.8705(6) 0.0376(12) Uani 1 1 d . U . . .
C11 C 0.6064(11) 0.5191(3) 0.6328(11) 0.031(2) Uani 0.5 1 d D U P A 1
H11A H 0.5329 0.5342 0.7066 0.038 Uiso 0.5 1 calc R U P A 1
H11B H 0.5358 0.5014 0.5604 0.038 Uiso 0.5 1 calc R U P A 1
C12 C 0.7151(12) 0.5552(3) 0.5531(11) 0.035(2) Uani 0.5 1 d D U P A 1
H12A H 0.7878 0.5393 0.4804 0.042 Uiso 0.5 1 calc R U P A 1
H12B H 0.6418 0.5773 0.4975 0.042 Uiso 0.5 1 calc R U P A 1
C13 C 0.8244(15) 0.5818(4) 0.6671(14) 0.040(3) Uani 0.5 1 d D U P A 1
H13A H 0.7513 0.6010 0.7309 0.048 Uiso 0.5 1 calc R U P A 1
H13B H 0.9004 0.6031 0.6134 0.048 Uiso 0.5 1 calc R U P A 1
C14 C 0.9302(11) 0.5488(3) 0.7665(11) 0.032(2) Uani 0.5 1 d D U P A 1
H14A H 1.0144 0.5326 0.7051 0.039 Uiso 0.5 1 calc R U P A 1
H14B H 0.9909 0.5670 0.8444 0.039 Uiso 0.5 1 calc R U P A 1
C15 C 0.8157(12) 0.5128(3) 0.8405(10) 0.030(2) Uani 0.5 1 d D U P A 1
H15A H 0.7329 0.5281 0.9055 0.036 Uiso 0.5 1 calc R U P A 1
H15B H 0.8821 0.4901 0.9004 0.036 Uiso 0.5 1 calc R U P A 1
C11A C 0.6879(12) 0.5317(3) 0.7814(10) 0.0285(19) Uani 0.5 1 d D U P A 2
H11C H 0.7719 0.5368 0.8627 0.034 Uiso 0.5 1 calc R U P A 2
H11D H 0.5770 0.5278 0.8282 0.034 Uiso 0.5 1 calc R U P A 2
C12A C 0.6821(12) 0.5749(3) 0.6839(11) 0.032(2) Uani 0.5 1 d D U P A 2
H12C H 0.6554 0.6022 0.7465 0.039 Uiso 0.5 1 calc R U P A 2
H12D H 0.5909 0.5714 0.6079 0.039 Uiso 0.5 1 calc R U P A 2
C13A C 0.8478(13) 0.5835(4) 0.6053(12) 0.030(2) Uani 0.5 1 d D U P A 2
H13C H 0.9378 0.5901 0.6802 0.036 Uiso 0.5 1 calc R U P A 2
H13D H 0.8367 0.6109 0.5385 0.036 Uiso 0.5 1 calc R U P A 2
C14A C 0.8935(12) 0.5405(3) 0.5145(11) 0.033(2) Uani 0.5 1 d D U P A 2
H14C H 1.0057 0.5447 0.4704 0.039 Uiso 0.5 1 calc R U P A 2
H14D H 0.8104 0.5360 0.4321 0.039 Uiso 0.5 1 calc R U P A 2
C15A C 0.8947(11) 0.4976(3) 0.6182(10) 0.0287(19) Uani 0.5 1 d D U P A 2
H15C H 0.9886 0.5010 0.6915 0.034 Uiso 0.5 1 calc R U P A 2
H15D H 0.9176 0.4696 0.5573 0.034 Uiso 0.5 1 calc R U P A 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
S1 O4 1.446(3) . ?
S1 O3 1.446(3) . ?
S1 N2 1.610(4) . ?
S1 C4 1.769(5) . ?
Na1 O7 2.296(4) . ?
Na1 O6 2.360(4) 4_665 ?
Na1 O5 2.385(4) . ?
Na1 O3 2.396(3) . ?
Na1 O4 2.470(3) 4_565 ?
Na1 O2 2.606(3) . ?
Na1 H7P 2.65(5) . ?
S2 O5 1.437(3) . ?
S2 O6 1.438(4) . ?
S2 N2 1.562(4) . ?
S2 C9 1.835(6) . ?
F1 C2 1.355(5) . ?
F2 C6 1.353(5) . ?
F3 C9 1.334(5) . ?
F4 C9 1.313(6) . ?
F5 C9 1.323(7) . ?
N1 C1 1.387(7) . ?
N1 C11A 1.436(8) . ?
N1 C11 1.446(9) . ?
N1 C15 1.537(9) . ?
N1 C15A 1.566(9) . ?
O1 C3 1.376(6) . ?
O1 C7 1.446(6) . ?
O2 C5 1.376(5) . ?
O2 C8 1.459(5) . ?
O4 Na1 2.470(3) 4_666 ?
O6 Na1 2.360(4) 4_566 ?
O7 H7O 0.840(19) . ?
O7 H7P 0.850(19) . ?
C1 C2 1.393(7) . ?
C1 C6 1.397(7) . ?
C2 C3 1.372(7) . ?
C3 C4 1.401(6) . ?
C4 C5 1.401(6) . ?
C5 C6 1.393(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C12 1.535(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.534(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.540(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.536(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11A C12A 1.518(10) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.527(10) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.527(11) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.544(10) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?

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
O4 S1 O3 115.28(19) . . ?
O4 S1 N2 106.62(19) . . ?
O3 S1 N2 111.3(2) . . ?
O4 S1 C4 107.8(2) . . ?
O3 S1 C4 109.4(2) . . ?
N2 S1 C4 106.0(2) . . ?
O7 Na1 O6 88.90(15) . 4_665 ?
O7 Na1 O5 104.61(14) . . ?
O6 Na1 O5 163.94(16) 4_665 . ?
O7 Na1 O3 162.87(14) . . ?
O6 Na1 O3 94.36(14) 4_665 . ?
O5 Na1 O3 75.31(11) . . ?
O7 Na1 O4 87.77(13) . 4_565 ?
O6 Na1 O4 90.27(13) 4_665 4_565 ?
O5 Na1 O4 81.77(12) . 4_565 ?
O3 Na1 O4 108.99(12) . 4_565 ?
O7 Na1 O2 97.36(12) . . ?
O6 Na1 O2 98.74(13) 4_665 . ?
O5 Na1 O2 88.26(12) . . ?
O3 Na1 O2 65.53(11) . . ?
O4 Na1 O2 169.68(12) 4_565 . ?
O7 Na1 H7P 18.0(7) . . ?
O6 Na1 H7P 90.5(12) 4_665 . ?
O5 Na1 H7P 99.7(12) . . ?
O3 Na1 H7P 175.0(12) . . ?
O4 Na1 H7P 69.9(7) 4_565 . ?
O2 Na1 H7P 114.8(8) . . ?
O5 S2 O6 117.9(2) . . ?
O5 S2 N2 116.5(2) . . ?
O6 S2 N2 110.2(2) . . ?
O5 S2 C9 103.3(2) . . ?
O6 S2 C9 102.7(3) . . ?
N2 S2 C9 103.8(2) . . ?
C1 N1 C11A 127.8(5) . . ?
C1 N1 C11 117.5(5) . . ?
C1 N1 C15 110.9(5) . . ?
C11 N1 C15 112.5(6) . . ?
C1 N1 C15A 120.4(5) . . ?
C11A N1 C15A 107.8(6) . . ?
C3 O1 C7 113.5(4) . . ?
C5 O2 C8 111.7(3) . . ?
C5 O2 Na1 123.2(3) . . ?
C8 O2 Na1 112.9(3) . . ?
S1 O3 Na1 129.85(18) . . ?
S1 O4 Na1 133.20(19) . 4_666 ?
S2 O5 Na1 134.0(2) . . ?
S2 O6 Na1 159.1(2) . 4_566 ?
Na1 O7 H7O 135(4) . . ?
Na1 O7 H7P 106(4) . . ?
H7O O7 H7P 108(4) . . ?
S2 N2 S1 121.9(2) . . ?
N1 C1 C2 126.0(4) . . ?
N1 C1 C6 119.6(5) . . ?
C2 C1 C6 114.4(5) . . ?
F1 C2 C3 117.3(5) . . ?
F1 C2 C1 119.0(5) . . ?
C3 C2 C1 123.6(4) . . ?
C2 C3 O1 120.3(4) . . ?
C2 C3 C4 120.4(4) . . ?
O1 C3 C4 118.8(4) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 S1 123.3(3) . . ?
C3 C4 S1 118.2(4) . . ?
O2 C5 C6 117.5(4) . . ?
O2 C5 C4 123.9(4) . . ?
C6 C5 C4 118.5(4) . . ?
F2 C6 C5 117.4(4) . . ?
F2 C6 C1 118.1(4) . . ?
C5 C6 C1 124.5(4) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F4 C9 F5 109.0(5) . . ?
F4 C9 F3 108.2(4) . . ?
F5 C9 F3 107.5(5) . . ?
F4 C9 S2 111.0(4) . . ?
F5 C9 S2 112.1(3) . . ?
F3 C9 S2 108.8(4) . . ?
N1 C11 C12 103.3(7) . . ?
N1 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C11 110.2(8) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 112.0(8) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 110.0(8) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 N1 102.7(7) . . ?
C14 C15 H15A 111.2 . . ?
N1 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
N1 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
N1 C11A C12A 115.4(7) . . ?
N1 C11A H11C 108.4 . . ?
C12A C11A H11C 108.4 . . ?
N1 C11A H11D 108.4 . . ?
C12A C11A H11D 108.4 . . ?
H11C C11A H11D 107.5 . . ?
C11A C12A C13A 112.4(8) . . ?
C11A C12A H12C 109.1 . . ?
C13A C12A H12C 109.1 . . ?
C11A C12A H12D 109.1 . . ?
C13A C12A H12D 109.1 . . ?
H12C C12A H12D 107.9 . . ?
C12A C13A C14A 109.3(8) . . ?
C12A C13A H13C 109.8 . . ?
C14A C13A H13C 109.8 . . ?
C12A C13A H13D 109.8 . . ?
C14A C13A H13D 109.8 . . ?
H13C C13A H13D 108.3 . . ?
C13A C14A C15A 109.0(8) . . ?
C13A C14A H14C 109.9 . . ?
C15A C14A H14C 109.9 . . ?
C13A C14A H14D 109.9 . . ?
C15A C14A H14D 109.9 . . ?
H14C C14A H14D 108.3 . . ?
C14A C15A N1 115.3(7) . . ?
C14A C15A H15C 108.4 . . ?
N1 C15A H15C 108.4 . . ?
C14A C15A H15D 108.4 . . ?
N1 C15A H15D 108.4 . . ?
H15C C15A H15D 107.5 . . ?

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
O7 H7O O1 0.840(19) 2.58(4) 3.264(5) 140(5) 1_554
O7 H7O N2 0.840(19) 2.33(4) 3.058(5) 145(5) 1_554

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.094

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_00000001
_database_code_depnum_ccdc_archive 'CCDC 1590313'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   5.399
_cell_length_b                   11.412
_cell_length_c                   18.037
_cell_angle_alpha                82.42
_cell_angle_beta                 82.1
_cell_angle_gamma                86.02
_cell_volume                     1089.67
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S1 S -0.00117445 0.557037 0.710108
O3 O -0.159026 0.634115 0.663798
O4 O -0.127621 0.47926 0.769504
N2 N 0.211425 0.486672 0.65686
S2 S 0.135597 0.397115 0.606996
O5 O -0.122156 0.403996 0.59374
O6 O 0.325993 0.392569 0.542748
C1 C 0.19264 0.64926 0.745813
C2 C 0.304149 0.742048 0.696401
O1 O 0.310351 0.745174 0.6198
C7 C 0.174125 0.845859 0.582177
H7A H 0.196486 0.918887 0.604119
H7B H -0.0069254 0.831906 0.588438
C8 C 0.278224 0.858064 0.500443
H8A H 0.457481 0.871315 0.495084
H8B H 0.191696 0.925341 0.473368
H8C H 0.253532 0.785476 0.479403
C3 C 0.437854 0.822313 0.72404
F1 F 0.380836 0.711347 0.921126
C4 C 0.465479 0.818012 0.800359
C5 C 0.363925 0.720117 0.846669
F2 F 0.558595 0.904385 0.673274
C6 C 0.230386 0.635868 0.822358
O2 O 0.125221 0.550733 0.874873
C9 C 0.285864 0.444367 0.886154
H9A H 0.442952 0.463595 0.903358
H9B H 0.32888 0.409861 0.838208
C10 C 0.150464 0.358958 0.943689
H10 H 0.110816 0.393376 0.991184
H10 H 0.255796 0.286155 0.951755
H10 H -0.00501299 0.340641 0.926316
N1 N 0.574611 0.903679 0.831383
C11 C 0.571481 1.02606 0.794662
H11 H 0.41685 1.04444 0.770576
H11 H 0.717239 1.03667 0.755008
C12 C 0.581573 1.10905 0.853438
H12 H 0.588376 1.19157 0.828393
H12 H 0.427184 1.1035 0.890102
C13 C 0.808097 1.07884 0.894953
H13 H 0.799167 1.12839 0.936469
H13 H 0.962159 1.09682 0.859868
C14 C 0.820206 0.947998 0.927331
H14 H 0.980149 0.928371 0.948314
H14 H 0.681585 0.933238 0.968903
C15 C 0.800796 0.8691 0.86737
H15 H 0.950449 0.875966 0.828901
H15 H 0.79426 0.78554 0.890554
C16 C 0.182539 0.251055 0.661146
F3 F 0.417929 0.234677 0.67491
F4 F 0.13791 0.166144 0.621718
F5 F 0.0327495 0.240516 0.725281
NA1 N 0.413848 0.428184 0.414704

#END
####################################################################### 
# 
# 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_X16186
_database_code_depnum_ccdc_archive 'CCDC 1590311'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 F5 N2 Na O6 S2'
_chemical_formula_weight         614.53

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'
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'
Na Na 0.0362 0.0249 '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                   43.264(4)
_cell_length_b                   5.5895(5)
_cell_length_c                   24.240(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.4805(16)
_cell_angle_gamma                90
_cell_volume                     5102.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7778
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.64

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7114
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            68773
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.081
_diffrn_reflns_theta_max         30.034
_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             7460
_reflns_number_gt                5851
_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 v2011.4.0 (Bruker-AXS, 2015)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+4.9374P] 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_number_reflns         7460
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_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
S1 S 0.40125(2) 0.91580(7) 0.39738(2) 0.01306(9) Uani 1 1 d . . . . .
S2 S 0.46586(2) 0.83660(7) 0.40425(2) 0.01243(9) Uani 1 1 d . . . . .
Na1 Na 0.54673(2) 0.63267(12) 0.53323(3) 0.01522(14) Uani 1 1 d . . . . .
F1 F 0.36372(2) 0.28405(17) 0.50214(4) 0.0160(2) Uani 1 1 d . . . . .
F2 F 0.28000(2) 0.50352(19) 0.29236(4) 0.0198(2) Uani 1 1 d . . . . .
F3 F 0.45395(3) 0.5787(2) 0.30630(5) 0.0329(3) Uani 1 1 d . . . . .
F4 F 0.42940(3) 0.9265(2) 0.28280(5) 0.0291(3) Uani 1 1 d . . . . .
F5 F 0.48582(3) 0.8930(2) 0.31962(5) 0.0292(3) Uani 1 1 d . . . . .
O1 O 0.41331(3) 0.5633(2) 0.49705(5) 0.0134(2) Uani 1 1 d . . . . .
O2 O 0.32428(3) 0.8037(2) 0.28611(5) 0.0156(2) Uani 1 1 d . . . . .
O3 O 0.38585(3) 1.0569(2) 0.34084(6) 0.0194(3) Uani 1 1 d . . . . .
O4 O 0.41430(3) 1.0484(2) 0.45585(5) 0.0175(2) Uani 1 1 d . . . . .
O5 O 0.49442(3) 0.6702(2) 0.43938(5) 0.0167(2) Uani 1 1 d . . . . .
O6 O 0.47256(3) 1.0870(2) 0.41835(6) 0.0181(2) Uani 1 1 d . . . . .
N1 N 0.29640(3) 0.2274(3) 0.40442(6) 0.0156(3) Uani 1 1 d . . . . .
N2 N 0.43154(3) 0.7335(2) 0.40151(6) 0.0135(3) Uani 1 1 d . . . . .
C1 C 0.37008(4) 0.7049(3) 0.39448(7) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.37873(4) 0.5685(3) 0.44867(7) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.35380(4) 0.4182(3) 0.44980(7) 0.0131(3) Uani 1 1 d . . . . .
C4 C 0.31936(4) 0.3869(3) 0.39864(7) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.31245(4) 0.5172(3) 0.34435(7) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.33650(4) 0.6723(3) 0.34106(7) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.28767(4) 0.2774(3) 0.45497(8) 0.0180(3) Uani 1 1 d . . . . .
H7A H 0.2681 0.3957 0.4397 0.022 Uiso 1 1 calc R U . . .
H7B H 0.3086 0.3465 0.4922 0.022 Uiso 1 1 calc R U . . .
C8 C 0.27650(5) 0.0482(3) 0.47420(8) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.2701 0.0841 0.5074 0.024 Uiso 1 1 calc R U . . .
H8B H 0.2966 -0.0663 0.4920 0.024 Uiso 1 1 calc R U . . .
C9 C 0.24476(5) -0.0635(3) 0.41697(9) 0.0221(4) Uani 1 1 d . . . . .
H9A H 0.2240 0.0445 0.4014 0.027 Uiso 1 1 calc R U . . .
H9B H 0.2385 -0.2174 0.4292 0.027 Uiso 1 1 calc R U . . .
C10 C 0.25424(5) -0.1052(3) 0.36482(8) 0.0215(4) Uani 1 1 d . . . . .
H10A H 0.2733 -0.2267 0.3793 0.026 Uiso 1 1 calc R U . . .
H10B H 0.2332 -0.1688 0.3267 0.026 Uiso 1 1 calc R U . . .
C11 C 0.26655(4) 0.1228(3) 0.34734(8) 0.0190(3) Uani 1 1 d . . . . .
H11A H 0.2741 0.0864 0.3158 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2467 0.2387 0.3282 0.023 Uiso 1 1 calc R U . . .
C12 C 0.45807(5) 0.8068(3) 0.32302(8) 0.0206(4) Uani 1 1 d . . . . .
C21 C 0.42048(4) 0.6130(3) 0.55937(7) 0.0140(3) Uani 1 1 d . . . . .
C22 C 0.40652(5) 0.8114(3) 0.57233(8) 0.0232(4) Uani 1 1 d . . . . .
H22 H 0.3903 0.9126 0.5392 0.028 Uiso 1 1 calc R U . . .
C23 C 0.41670(6) 0.8607(3) 0.63526(9) 0.0269(4) Uani 1 1 d . . . . .
H23 H 0.4072 0.9968 0.6452 0.032 Uiso 1 1 calc R U . . .
C24 C 0.44039(5) 0.7142(4) 0.68331(8) 0.0259(4) Uani 1 1 d . . . . .
H24 H 0.4477 0.7514 0.7262 0.031 Uiso 1 1 calc R U . . .
C25 C 0.45344(5) 0.5122(4) 0.66855(8) 0.0294(4) Uani 1 1 d . . . . .
H25 H 0.4693 0.4088 0.7015 0.035 Uiso 1 1 calc R U . . .
C26 C 0.44351(5) 0.4601(3) 0.60600(8) 0.0224(4) Uani 1 1 d . . . . .
H26 H 0.4524 0.3220 0.5956 0.027 Uiso 1 1 calc R U . . .
C31 C 0.33584(4) 0.7383(3) 0.24368(7) 0.0149(3) Uani 1 1 d . . . . .
C32 C 0.35340(4) 0.5271(3) 0.24828(8) 0.0180(3) Uani 1 1 d . . . . .
H32 H 0.3582 0.4162 0.2812 0.022 Uiso 1 1 calc R U . . .
C33 C 0.36405(5) 0.4795(3) 0.20355(8) 0.0214(4) Uani 1 1 d . . . . .
H33 H 0.3763 0.3352 0.2063 0.026 Uiso 1 1 calc R U . . .
C34 C 0.35689(5) 0.6403(4) 0.15518(8) 0.0236(4) Uani 1 1 d . . . . .
H34 H 0.3642 0.6067 0.1249 0.028 Uiso 1 1 calc R U . . .
C35 C 0.33891(5) 0.8508(3) 0.15130(8) 0.0229(4) Uani 1 1 d . . . . .
H35 H 0.3338 0.9610 0.1181 0.027 Uiso 1 1 calc R U . . .
C36 C 0.32831(4) 0.9018(3) 0.19550(8) 0.0185(3) Uani 1 1 d . . . . .
H36 H 0.3161 1.0462 0.1929 0.022 Uiso 1 1 calc R U . . .


_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
S1 O3 1.4301(12) . ?
S1 O4 1.4454(12) . ?
S1 N2 1.6234(14) . ?
S1 C1 1.7665(16) . ?
S1 Na1 3.2461(8) 5_676 ?
S2 O6 1.4362(13) . ?
S2 O5 1.4426(12) . ?
S2 N2 1.5635(13) . ?
S2 C12 1.8347(17) . ?
S2 Na1 3.2071(8) 5_666 ?
Na1 O5 2.2964(13) . ?
Na1 O6 2.3435(13) 5_676 ?
Na1 O4 2.3771(13) 5_676 ?
Na1 O1 2.4449(12) 5_666 ?
Na1 N2 2.4723(15) 5_666 ?
Na1 O5 2.7642(13) 5_666 ?
Na1 S2 3.2071(8) 5_666 ?
Na1 S1 3.2462(8) 5_676 ?
Na1 Na1 3.8384(13) 5_666 ?
F1 C3 1.3491(17) . ?
F2 C5 1.3506(17) . ?
F3 C12 1.323(2) . ?
F4 C12 1.321(2) . ?
F5 C12 1.3332(19) . ?
O1 C2 1.3737(18) . ?
O1 C21 1.4122(17) . ?
O1 Na1 2.4449(12) 5_666 ?
O2 C6 1.3785(18) . ?
O2 C31 1.3957(18) . ?
O4 Na1 2.3772(13) 5_676 ?
O5 Na1 2.7642(13) 5_666 ?
O6 Na1 2.3435(13) 5_676 ?
N1 C4 1.392(2) . ?
N1 C11 1.472(2) . ?
N1 C7 1.4756(19) . ?
N2 Na1 2.4723(15) 5_666 ?
C1 C2 1.401(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.378(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.387(2) . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C21 C22 1.371(2) . ?
C21 C26 1.376(2) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.378(2) . ?
C31 C36 1.389(2) . ?
C32 C33 1.397(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 115.46(8) . . ?
O3 S1 N2 112.75(7) . . ?
O4 S1 N2 110.33(7) . . ?
O3 S1 C1 110.07(7) . . ?
O4 S1 C1 107.65(7) . . ?
N2 S1 C1 99.26(7) . . ?
O3 S1 Na1 86.86(5) . 5_676 ?
O4 S1 Na1 41.98(5) . 5_676 ?
N2 S1 Na1 97.08(5) . 5_676 ?
C1 S1 Na1 149.37(5) . 5_676 ?
O6 S2 O5 118.29(7) . . ?
O6 S2 N2 116.45(7) . . ?
O5 S2 N2 107.90(7) . . ?
O6 S2 C12 104.64(8) . . ?
O5 S2 C12 103.09(7) . . ?
N2 S2 C12 104.60(7) . . ?
O6 S2 Na1 138.25(5) . 5_666 ?
O5 S2 Na1 59.29(5) . 5_666 ?
N2 S2 Na1 48.71(5) . 5_666 ?
C12 S2 Na1 116.67(6) . 5_666 ?
O5 Na1 O6 90.85(5) . 5_676 ?
O5 Na1 O4 109.93(5) . 5_676 ?
O6 Na1 O4 81.41(4) 5_676 5_676 ?
O5 Na1 O1 103.96(4) . 5_666 ?
O6 Na1 O1 158.22(5) 5_676 5_666 ?
O4 Na1 O1 78.58(4) 5_676 5_666 ?
O5 Na1 N2 126.06(5) . 5_666 ?
O6 Na1 N2 110.49(5) 5_676 5_666 ?
O4 Na1 N2 121.61(5) 5_676 5_666 ?
O1 Na1 N2 73.66(4) 5_666 5_666 ?
O5 Na1 O5 81.76(4) . 5_666 ?
O6 Na1 O5 81.89(4) 5_676 5_666 ?
O4 Na1 O5 159.70(4) 5_676 5_666 ?
O1 Na1 O5 115.59(4) 5_666 5_666 ?
N2 Na1 O5 55.00(4) 5_666 5_666 ?
O5 Na1 S2 103.25(4) . 5_666 ?
O6 Na1 S2 97.18(4) 5_676 5_666 ?
O4 Na1 S2 146.80(4) 5_676 5_666 ?
O1 Na1 S2 94.88(3) 5_666 5_666 ?
N2 Na1 S2 28.37(3) 5_666 5_666 ?
O5 Na1 S2 26.66(2) 5_666 5_666 ?
O5 Na1 S1 122.42(4) . 5_676 ?
O6 Na1 S1 63.11(3) 5_676 5_676 ?
O4 Na1 S1 24.00(3) 5_676 5_676 ?
O1 Na1 S1 95.25(3) 5_666 5_676 ?
N2 Na1 S1 111.33(4) 5_666 5_676 ?
O5 Na1 S1 135.72(3) 5_666 5_676 ?
S2 Na1 S1 128.80(2) 5_666 5_676 ?
O5 Na1 Na1 45.46(3) . 5_666 ?
O6 Na1 Na1 84.68(4) 5_676 5_666 ?
O4 Na1 Na1 151.56(4) 5_676 5_666 ?
O1 Na1 Na1 117.09(4) 5_666 5_666 ?
N2 Na1 Na1 86.51(4) 5_666 5_666 ?
O5 Na1 Na1 36.31(3) 5_666 5_666 ?
S2 Na1 Na1 59.571(18) 5_666 5_666 ?
S1 Na1 Na1 146.76(3) 5_676 5_666 ?
C2 O1 C21 118.87(12) . . ?
C2 O1 Na1 112.77(9) . 5_666 ?
C21 O1 Na1 126.42(9) . 5_666 ?
C6 O2 C31 117.80(12) . . ?
S1 O4 Na1 114.02(6) . 5_676 ?
S2 O5 Na1 141.62(7) . . ?
S2 O5 Na1 94.05(6) . 5_666 ?
Na1 O5 Na1 98.24(4) . 5_666 ?
S2 O6 Na1 133.70(7) . 5_676 ?
C4 N1 C11 119.94(13) . . ?
C4 N1 C7 116.69(13) . . ?
C11 N1 C7 113.04(13) . . ?
S2 N2 S1 119.48(9) . . ?
S2 N2 Na1 102.93(7) . 5_666 ?
S1 N2 Na1 126.90(7) . 5_666 ?
C2 C1 C6 118.18(14) . . ?
C2 C1 S1 118.63(12) . . ?
C6 C1 S1 123.16(12) . . ?
O1 C2 C3 120.28(14) . . ?
O1 C2 C1 119.24(14) . . ?
C3 C2 C1 119.98(14) . . ?
F1 C3 C2 117.87(13) . . ?
F1 C3 C4 118.03(14) . . ?
C2 C3 C4 124.01(14) . . ?
N1 C4 C5 126.46(14) . . ?
N1 C4 C3 119.38(14) . . ?
C5 C4 C3 114.08(14) . . ?
F2 C5 C6 116.53(13) . . ?
F2 C5 C4 119.36(14) . . ?
C6 C5 C4 124.03(14) . . ?
O2 C6 C5 116.54(13) . . ?
O2 C6 C1 123.59(14) . . ?
C5 C6 C1 119.58(14) . . ?
N1 C7 C8 110.14(14) . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 110.23(14) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 109.09(14) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C9 112.12(15) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 C10 109.69(13) . . ?
N1 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
F4 C12 F3 109.00(15) . . ?
F4 C12 F5 108.58(14) . . ?
F3 C12 F5 108.61(14) . . ?
F4 C12 S2 110.84(12) . . ?
F3 C12 S2 109.99(12) . . ?
F5 C12 S2 109.77(12) . . ?
C22 C21 C26 122.48(15) . . ?
C22 C21 O1 120.96(14) . . ?
C26 C21 O1 116.47(14) . . ?
C21 C22 C23 118.28(16) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C24 C23 C22 120.73(17) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.57(16) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.44(17) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 118.46(17) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C32 C31 C36 121.53(15) . . ?
C32 C31 O2 123.23(14) . . ?
C36 C31 O2 115.24(15) . . ?
C31 C32 C33 118.68(16) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
C34 C33 C32 120.76(17) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.43(16) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C36 C35 C34 120.62(16) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 118.97(17) . . ?
C35 C36 H36 120.5 . . ?
C31 C36 H36 120.5 . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_X16212
_database_code_depnum_ccdc_archive 'CCDC 1590312'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 F6 N3 O4 S2'
_chemical_formula_weight         509.49

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.1529(9)
_cell_length_b                   11.0518(12)
_cell_length_c                   12.5361(14)
_cell_angle_alpha                99.4303(16)
_cell_angle_beta                 94.0750(16)
_cell_angle_gamma                110.5628(15)
_cell_volume                     1033.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.343
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5927
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            77103
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.663
_diffrn_reflns_theta_max         31.032
_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             6597
_reflns_number_gt                5992
_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 v2011.4.0 (Bruker-AXS, 2015)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.5504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6597
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
S1 S 0.63513(3) 0.65075(2) 0.40915(2) 0.01223(6) Uani 1 1 d . . . . .
S2 S 0.72239(3) 0.78152(2) 0.23688(2) 0.01342(6) Uani 1 1 d . . . . .
F1 F -0.03764(9) 0.50533(7) 0.28530(6) 0.01925(14) Uani 1 1 d . . . . .
F2 F 0.54756(9) 0.38159(7) 0.28340(6) 0.02065(14) Uani 1 1 d . . . . .
F3 F 0.25124(10) 0.21402(7) 0.16811(6) 0.01984(14) Uani 1 1 d . . . . .
F4 F 0.49523(9) 0.56466(7) 0.11010(6) 0.02066(14) Uani 1 1 d . . . . .
F5 F 0.76603(10) 0.60872(8) 0.08132(7) 0.02616(16) Uani 1 1 d . . . . .
F6 F 0.61976(11) 0.72143(8) 0.02628(6) 0.02412(16) Uani 1 1 d . . . . .
O1 O 0.60681(10) 0.76077(8) 0.47520(7) 0.01617(15) Uani 1 1 d . . . . .
O2 O 0.71280(11) 0.57819(9) 0.46724(7) 0.01799(16) Uani 1 1 d . . . . .
O3 O 0.57753(11) 0.82523(8) 0.25351(7) 0.01938(16) Uani 1 1 d . . . . .
O4 O 0.88798(11) 0.87400(8) 0.21983(7) 0.02124(17) Uani 1 1 d . . . . .
N1 N -0.05409(16) 0.27895(10) 0.14404(10) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.26835(11) 0.69514(8) 0.40156(7) 0.01112(15) Uani 1 1 d D . . . .
H2 H 0.3808(17) 0.7383(14) 0.4281(12) 0.013 Uiso 1 1 d D U . . .
N3 N 0.75503(12) 0.69406(9) 0.31720(8) 0.01403(16) Uani 1 1 d . . . . .
C1 C 0.09617(15) 0.35759(10) 0.21335(9) 0.01475(19) Uani 1 1 d . . . . .
C2 C 0.11206(14) 0.47967(10) 0.27833(9) 0.01399(18) Uani 1 1 d . . . . .
C3 C 0.26832(13) 0.57116(10) 0.33776(8) 0.01172(17) Uani 1 1 d . . . . .
C4 C 0.42213(13) 0.54094(10) 0.34179(8) 0.01175(17) Uani 1 1 d . . . . .
C5 C 0.40563(14) 0.41638(10) 0.28559(9) 0.01380(18) Uani 1 1 d . . . . .
C6 C 0.24969(15) 0.32805(10) 0.22428(9) 0.01463(19) Uani 1 1 d . . . . .
C7 C 0.64701(15) 0.66201(11) 0.10626(9) 0.01573(19) Uani 1 1 d . . . . .
C11 C -0.16227(19) 0.33606(12) 0.08587(11) 0.0248(3) Uani 1 1 d . . . . .
H11A H -0.0981 0.4324 0.0950 0.030 Uiso 1 1 calc R U . . .
H11B H -0.2743 0.3215 0.1170 0.030 Uiso 1 1 calc R U . . .
C12 C -0.20223(15) 0.27227(11) -0.03476(10) 0.0182(2) Uani 1 1 d . . . . .
H12A H -0.0908 0.2952 -0.0673 0.022 Uiso 1 1 calc R U . . .
H12B H -0.2814 0.3071 -0.0726 0.022 Uiso 1 1 calc R U . . .
C13 C -0.29003(18) 0.12273(12) -0.05145(10) 0.0241(2) Uani 1 1 d . . . . .
H13A H -0.3093 0.0830 -0.1302 0.029 Uiso 1 1 calc R U . . .
H13B H -0.4066 0.0991 -0.0250 0.029 Uiso 1 1 calc R U . . .
C14 C -0.17276(18) 0.06867(11) 0.01085(10) 0.0216(2) Uani 1 1 d . . . . .
H14A H -0.2338 -0.0277 0.0035 0.026 Uiso 1 1 calc R U . . .
H14B H -0.0612 0.0842 -0.0210 0.026 Uiso 1 1 calc R U . . .
C15 C -0.13084(15) 0.13476(10) 0.13111(9) 0.0173(2) Uani 1 1 d . . . . .
H15A H -0.2405 0.1095 0.1653 0.021 Uiso 1 1 calc R U . . .
H15B H -0.0464 0.1041 0.1686 0.021 Uiso 1 1 calc R U . . .
C21 C 0.20606(14) 0.77826(10) 0.33539(9) 0.01379(18) Uani 1 1 d . . . . .
H21A H 0.0773 0.7349 0.3105 0.017 Uiso 1 1 calc R U . . .
H21B H 0.2678 0.7879 0.2703 0.017 Uiso 1 1 calc R U . . .
C22 C 0.24639(15) 0.91327(10) 0.40712(10) 0.0177(2) Uani 1 1 d . . . . .
H22A H 0.2032 0.9675 0.3655 0.021 Uiso 1 1 calc R U . . .
H22B H 0.3760 0.9584 0.4273 0.021 Uiso 1 1 calc R U . . .
C23 C 0.15882(17) 0.90183(11) 0.51101(10) 0.0208(2) Uani 1 1 d . . . . .
H23A H 0.1953 0.9904 0.5585 0.025 Uiso 1 1 calc R U . . .
H23B H 0.0286 0.8674 0.4914 0.025 Uiso 1 1 calc R U . . .
C24 C 0.21101(16) 0.80989(11) 0.57308(9) 0.0197(2) Uani 1 1 d . . . . .
H24A H 0.3388 0.8508 0.6014 0.024 Uiso 1 1 calc R U . . .
H24B H 0.1449 0.7983 0.6363 0.024 Uiso 1 1 calc R U . . .
C25 C 0.17270(14) 0.67530(10) 0.50097(9) 0.01507(19) Uani 1 1 d . . . . .
H25A H 0.2143 0.6200 0.5422 0.018 Uiso 1 1 calc R U . . .
H25B H 0.0438 0.6300 0.4776 0.018 Uiso 1 1 calc R U . . .


_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
S1 O2 1.4341(8) . ?
S1 O1 1.4533(8) . ?
S1 N3 1.5892(9) . ?
S1 C4 1.7823(11) . ?
S2 O4 1.4339(9) . ?
S2 O3 1.4404(9) . ?
S2 N3 1.5749(9) . ?
S2 C7 1.8389(12) . ?
F1 C2 1.3521(12) . ?
F2 C5 1.3421(12) . ?
F3 C6 1.3438(11) . ?
F4 C7 1.3346(12) . ?
F5 C7 1.3305(13) . ?
F6 C7 1.3313(13) . ?
N1 C1 1.3654(14) . ?
N1 C15 1.4689(14) . ?
N1 C11 1.4692(15) . ?
N2 C3 1.4689(12) . ?
N2 C21 1.5189(13) . ?
N2 C25 1.5222(13) . ?
N2 H2 0.881(12) . ?
C1 C6 1.4033(15) . ?
C1 C2 1.4151(14) . ?
C2 C3 1.3834(14) . ?
C3 C4 1.4062(14) . ?
C4 C5 1.3958(14) . ?
C5 C6 1.3796(15) . ?
C11 C12 1.5197(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5238(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5262(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5211(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 C22 1.5221(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5312(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5280(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5231(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

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
O2 S1 O1 116.05(5) . . ?
O2 S1 N3 106.38(5) . . ?
O1 S1 N3 112.62(5) . . ?
O2 S1 C4 108.21(5) . . ?
O1 S1 C4 105.90(5) . . ?
N3 S1 C4 107.32(5) . . ?
O4 S2 O3 119.16(5) . . ?
O4 S2 N3 110.10(5) . . ?
O3 S2 N3 115.70(5) . . ?
O4 S2 C7 103.31(5) . . ?
O3 S2 C7 104.22(5) . . ?
N3 S2 C7 101.70(5) . . ?
C1 N1 C15 123.71(10) . . ?
C1 N1 C11 121.08(10) . . ?
C15 N1 C11 114.85(10) . . ?
C3 N2 C21 114.76(8) . . ?
C3 N2 C25 112.75(8) . . ?
C21 N2 C25 111.43(8) . . ?
C3 N2 H2 102.9(10) . . ?
C21 N2 H2 108.9(10) . . ?
C25 N2 H2 105.2(10) . . ?
S2 N3 S1 123.62(6) . . ?
N1 C1 C6 123.75(10) . . ?
N1 C1 C2 122.29(10) . . ?
C6 C1 C2 113.93(9) . . ?
F1 C2 C3 118.37(9) . . ?
F1 C2 C1 117.17(9) . . ?
C3 C2 C1 124.41(10) . . ?
C2 C3 C4 119.67(9) . . ?
C2 C3 N2 119.36(9) . . ?
C4 C3 N2 120.85(9) . . ?
C5 C4 C3 116.71(9) . . ?
C5 C4 S1 118.23(8) . . ?
C3 C4 S1 125.04(8) . . ?
F2 C5 C6 117.04(9) . . ?
F2 C5 C4 120.16(10) . . ?
C6 C5 C4 122.64(10) . . ?
F3 C6 C5 117.73(10) . . ?
F3 C6 C1 119.88(10) . . ?
C5 C6 C1 122.24(9) . . ?
F5 C7 F6 108.34(9) . . ?
F5 C7 F4 108.14(9) . . ?
F6 C7 F4 107.96(9) . . ?
F5 C7 S2 111.33(8) . . ?
F6 C7 S2 110.05(8) . . ?
F4 C7 S2 110.92(7) . . ?
N1 C11 C12 109.88(10) . . ?
N1 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C13 111.08(10) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 109.84(10) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 110.87(10) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C15 C14 110.61(10) . . ?
N1 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N2 C21 C22 108.60(8) . . ?
N2 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
N2 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 C23 111.44(9) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 110.92(9) . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 111.94(9) . . ?
C25 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N2 C25 C24 108.60(9) . . ?
N2 C25 H25A 110.0 . . ?
C24 C25 H25A 110.0 . . ?
N2 C25 H25B 110.0 . . ?
C24 C25 H25B 110.0 . . ?
H25A C25 H25B 108.4 . . ?

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
N2 H2 S1 0.881(12) 2.588(14) 3.1933(10) 126.7(12) .
N2 H2 O1 0.881(12) 1.812(13) 2.6468(12) 157.4(14) .

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.056

