# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_xtr95
_database_code_depnum_ccdc_archive 'CCDC 2183953'
loop_
_audit_author_name
_audit_author_address
'Xiaogang Tong'
;Yunnan University
China
;
_audit_update_record             
;
2022-07-05 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H22 F4 N2 O4 S'
_chemical_formula_sum            'C24 H22 F4 N2 O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         510.49

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1699(3)
_cell_length_b                   10.9182(3)
_cell_length_c                   22.3255(7)
_cell_angle_alpha                76.1900(10)
_cell_angle_beta                 83.8180(10)
_cell_angle_gamma                75.0440(10)
_cell_volume                     2322.94(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      4.3329
_cell_measurement_theta_max      72.3662
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056

_exptl_absorpt_coefficient_mu    1.842
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            42065
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         72.36
_diffrn_reflns_theta_full        72.36
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             9080
_reflns_number_gt                8872
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1632
_refine_ls_goodness_of_fit_ref   1.492
_refine_ls_restrained_S_all      1.492
_refine_ls_number_reflns         9080
_refine_ls_number_parameters     638
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.255
_refine_diff_density_min         -1.188
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0280(11)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.15777(3) 1.16713(3) 0.83538(2) 0.02227(14) Uani d . . . 1 . .
S S2 1.06810(3) 0.65384(3) 0.33178(2) 0.02185(14) Uani d . . . 1 . .
F F1 0.86444(10) 0.94029(10) 0.43312(4) 0.0372(2) Uani d . . . 1 . .
F F2 0.27545(9) 1.00955(10) 0.93409(4) 0.0330(2) Uani d . . . 1 . .
F F3 0.12048(12) 1.17417(10) 0.95238(5) 0.0400(3) Uani d . . . 1 . .
F F4 0.06417(10) 1.01437(9) 0.92975(4) 0.0322(2) Uani d . . . 1 . .
F F5 0.70146(10) 0.42053(10) -0.07394(4) 0.0378(2) Uani d . . . 1 . .
F F6 1.20262(9) 0.50294(10) 0.42602(4) 0.0326(2) Uani d . . . 1 . .
F F7 1.06144(11) 0.67423(10) 0.44617(4) 0.0359(2) Uani d . . . 1 . .
F F8 0.98767(10) 0.51314(10) 0.43470(4) 0.0333(2) Uani d . . . 1 . .
O O1 0.54087(10) 1.04546(9) 0.83656(4) 0.0226(2) Uani d . . . 1 . .
O O2 0.26254(11) 1.23538(10) 0.82758(5) 0.0293(2) Uani d . . . 1 . .
O O3 0.01861(11) 1.23317(10) 0.82527(5) 0.0296(3) Uani d . . . 1 . .
O O4 0.57887(11) 0.84754(10) 0.90312(5) 0.0298(3) Uani d . . . 1 . .
O O5 0.76317(10) 0.52224(10) 0.34249(5) 0.0245(2) Uani d . . . 1 . .
O O6 1.17280(12) 0.72301(11) 0.31837(5) 0.0313(3) Uani d . . . 1 . .
O O7 0.92808(11) 0.71747(10) 0.32434(5) 0.0286(2) Uani d . . . 1 . .
O O8 0.79869(11) 0.31607(11) 0.40021(5) 0.0312(3) Uani d . . . 1 . .
N N1 0.42556(11) 0.90242(11) 0.82805(5) 0.0205(2) Uani d . . . 1 . .
N N3 0.20201(11) 1.04924(12) 0.80116(5) 0.0217(3) Uani d . . . 1 . .
N N4 0.95802(12) 0.37954(11) 0.32792(5) 0.0217(3) Uani d . . . 1 . .
N N5 1.10738(12) 0.53032(11) 0.30111(5) 0.0211(3) Uani d . . . 1 . .
C C1 0.55019(18) 1.12748(18) 0.92814(7) 0.0350(4) Uani d . . . 1 . .
H H13 0.4572 1.179705 0.920222 0.053 Uiso calc U . R 1 . .
H H12 0.598911 1.174213 0.946975 0.053 Uiso calc U . R 1 . .
H H1 0.546888 1.044212 0.956258 0.053 Uiso calc U . R 1 . .
C C2 0.62382(14) 1.10319(14) 0.86776(7) 0.0250(3) Uani d . . . 1 . .
C C3 0.52142(13) 0.92667(13) 0.86058(6) 0.0214(3) Uani d . . . 1 . .
C C4 0.34516(13) 0.99655(13) 0.77965(6) 0.0202(3) Uani d . . . 1 . .
H H5 0.391306 1.067141 0.758723 0.024 Uiso calc U . R 1 . .
C C5 0.32393(13) 0.91484(13) 0.73385(6) 0.0207(3) Uani d . . . 1 . .
C C6 0.41877(14) 0.92306(13) 0.67951(6) 0.0231(3) Uani d . . . 1 . .
C C7 0.58860(14) 0.93259(14) 0.58165(6) 0.0238(3) Uani d . . . 1 . .
C C8 0.66450(15) 0.81671(15) 0.56643(7) 0.0264(3) Uani d . . . 1 . .
H H22 0.652205 0.735796 0.590625 0.032 Uiso calc U . R 1 . .
C C9 0.75771(15) 0.81925(15) 0.51618(7) 0.0276(3) Uani d . . . 1 . .
H H2 0.809847 0.740839 0.50576 0.033 Uiso calc U . R 1 . .
C C10 0.77292(15) 0.93809(16) 0.48175(6) 0.0276(3) Uani d . . . 1 . .
C C11 0.60606(15) 1.05095(15) 0.54514(7) 0.0266(3) Uani d . . . 1 . .
H H3 0.553631 1.129903 0.554918 0.032 Uiso calc U . R 1 . .
C C12 0.69893(16) 1.05490(15) 0.49477(7) 0.0284(3) Uani d . . . 1 . .
H H4 0.711251 1.135345 0.470025 0.034 Uiso calc U . R 1 . .
C C13 0.17378(14) 0.96658(14) 0.71734(6) 0.0232(3) Uani d . . . 1 . .
H H20 0.161669 1.045432 0.683572 0.028 Uiso calc U . R 1 . .
H H21 0.139573 0.899961 0.704677 0.028 Uiso calc U . R 1 . .
C C14 0.10117(14) 0.99772(14) 0.77698(7) 0.0234(3) Uani d . . . 1 . .
H H18 0.014047 1.06381 0.769 0.028 Uiso calc U . R 1 . .
H H19 0.083435 0.918857 0.805875 0.028 Uiso calc U . R 1 . .
C C15 0.15512(15) 1.08641(15) 0.91779(6) 0.0245(3) Uani d . . . 1 . .
C C16 0.62607(18) 1.23011(16) 0.82186(7) 0.0318(3) Uani d . . . 1 . .
H H8 0.672443 1.211683 0.783038 0.048 Uiso calc U . R 1 . .
H H7 0.674802 1.279863 0.838776 0.048 Uiso calc U . R 1 . .
H H6 0.532425 1.280736 0.814139 0.048 Uiso calc U . R 1 . .
C C17 0.76760(16) 1.01843(18) 0.87654(9) 0.0385(4) Uani d . . . 1 . .
H H9 0.765584 0.94063 0.909058 0.058 Uiso calc U . R 1 . .
H H10 0.825186 1.06731 0.888414 0.058 Uiso calc U . R 1 . .
H H11 0.804755 0.992688 0.837804 0.058 Uiso calc U . R 1 . .
C C18 0.41159(13) 0.77603(13) 0.82870(6) 0.0211(3) Uani d . . . 1 . .
C C19 0.44815(13) 0.66128(14) 0.87309(6) 0.0234(3) Uani d . . . 1 . .
H H14 0.488348 0.65909 0.909938 0.028 Uiso calc U . R 1 . .
C C20 0.42334(15) 0.54940(14) 0.86129(7) 0.0271(3) Uani d . . . 1 . .
H H17 0.448538 0.469344 0.890466 0.032 Uiso calc U . R 1 . .
C C21 0.36252(15) 0.55240(14) 0.80773(8) 0.0289(3) Uani d . . . 1 . .
H H16 0.345885 0.475116 0.801022 0.035 Uiso calc U . R 1 . .
C C22 0.32615(15) 0.66826(15) 0.76412(7) 0.0264(3) Uani d . . . 1 . .
H H15 0.284289 0.671077 0.727613 0.032 Uiso calc U . R 1 . .
C C23 0.35201(13) 0.77942(13) 0.77482(6) 0.0218(3) Uani d . . . 1 . .
C C24 0.76834(15) 0.42064(16) -0.02442(6) 0.0279(3) Uani d . . . 1 . .
C C25 0.83428(16) 0.30183(16) 0.00981(7) 0.0296(3) Uani d . . . 1 . .
H H25 0.833603 0.223214 -0.001258 0.035 Uiso calc U . R 1 . .
C C26 0.90158(15) 0.30066(15) 0.06088(7) 0.0274(3) Uani d . . . 1 . .
H H24 0.9484 0.220199 0.085028 0.033 Uiso calc U . R 1 . .
C C27 0.90117(14) 0.41658(15) 0.07713(6) 0.0252(3) Uani d . . . 1 . .
C C28 0.96763(15) 0.41311(15) 0.13119(7) 0.0265(3) Uani d . . . 1 . .
C C29 1.02094(14) 0.40861(14) 0.17740(6) 0.0244(3) Uani d . . . 1 . .
C C30 1.09304(13) 0.39896(13) 0.23237(6) 0.0216(3) Uani d . . . 1 . .
C C31 1.00515(13) 0.47685(13) 0.27948(6) 0.0198(3) Uani d . . . 1 . .
H H26 0.927914 0.546788 0.259652 0.024 Uiso calc U . R 1 . .
C C32 0.83423(14) 0.40013(13) 0.36092(6) 0.0222(3) Uani d . . . 1 . .
C C33 0.62916(14) 0.57031(14) 0.37290(6) 0.0255(3) Uani d . . . 1 . .
C C34 0.64704(17) 0.56550(17) 0.44010(7) 0.0334(3) Uani d . . . 1 . .
H H23 0.680156 0.475 0.461884 0.05 Uiso calc U . R 1 . .
H H37 0.559336 0.6032 0.459262 0.05 Uiso calc U . R 1 . .
H H38 0.713181 0.615203 0.442554 0.05 Uiso calc U . R 1 . .
C C35 0.76656(16) 0.53738(16) -0.01094(7) 0.0310(3) Uani d . . . 1 . .
H H44 0.721014 0.617323 -0.035949 0.037 Uiso calc U . R 1 . .
C C36 0.83395(16) 0.53447(15) 0.04076(7) 0.0291(3) Uani d . . . 1 . .
H H43 0.834123 0.613669 0.051369 0.035 Uiso calc U . R 1 . .
C C37 1.12164(14) 0.26101(14) 0.27141(6) 0.0230(3) Uani d . . . 1 . .
C C38 1.04096(13) 0.25395(13) 0.32603(6) 0.0213(3) Uani d . . . 1 . .
C C39 1.24825(14) 0.48014(14) 0.27698(6) 0.0231(3) Uani d . . . 1 . .
H H28 1.295647 0.39991 0.305184 0.028 Uiso calc U . R 1 . .
H H27 1.302619 0.545943 0.270257 0.028 Uiso calc U . R 1 . .
C C40 1.22146(14) 0.45307(14) 0.21635(6) 0.0238(3) Uani d . . . 1 . .
H H29 1.29915 0.388431 0.202588 0.029 Uiso calc U . R 1 . .
H H30 1.204406 0.533669 0.183607 0.029 Uiso calc U . R 1 . .
C C41 1.08000(15) 0.58194(15) 0.41474(6) 0.0239(3) Uani d . . . 1 . .
C C42 0.58689(17) 0.70947(17) 0.33656(8) 0.0363(4) Uani d . . . 1 . .
H H31 0.654355 0.756604 0.340525 0.055 Uiso calc U . R 1 . .
H H33 0.497621 0.751741 0.352741 0.055 Uiso calc U . R 1 . .
H H32 0.581394 0.709975 0.292945 0.055 Uiso calc U . R 1 . .
C C43 0.52971(16) 0.4930(2) 0.36530(9) 0.0398(4) Uani d . . . 1 . .
H H35 0.530486 0.489769 0.321766 0.06 Uiso calc U . R 1 . .
H H36 0.437768 0.534824 0.378932 0.06 Uiso calc U . R 1 . .
H H34 0.556772 0.404398 0.390319 0.06 Uiso calc U . R 1 . .
C C44 1.04709(14) 0.13717(14) 0.36852(7) 0.0251(3) Uani d . . . 1 . .
H H39 0.993482 0.132872 0.406191 0.03 Uiso calc U . R 1 . .
C C45 1.13532(15) 0.02612(14) 0.35366(7) 0.0288(3) Uani d . . . 1 . .
H H42 1.140448 -0.055514 0.381525 0.035 Uiso calc U . R 1 . .
C C46 1.21574(15) 0.03213(15) 0.29915(8) 0.0311(3) Uani d . . . 1 . .
H H40 1.27501 -0.044921 0.290268 0.037 Uiso calc U . R 1 . .
C C47 1.20990(15) 0.15031(15) 0.25753(7) 0.0279(3) Uani d . . . 1 . .
H H41 1.26525 0.155126 0.220344 0.033 Uiso calc U . R 1 . .
C C49 0.49480(15) 0.92825(14) 0.63462(7) 0.0247(3) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.4244(12) ?
S1 O3 . 1.4277(11) ?
S1 N3 . 1.5935(12) ?
S1 C15 . 1.8412(15) ?
S2 O7 . 1.4225(11) ?
S2 O6 . 1.4256(12) ?
S2 N5 . 1.5971(12) ?
S2 C41 . 1.8347(14) ?
F1 C10 . 1.3516(17) ?
F2 C15 . 1.3244(17) ?
F3 C15 . 1.3261(17) ?
F4 C15 . 1.3295(18) ?
F5 C24 . 1.3595(16) ?
F6 C41 . 1.3309(17) ?
F7 C41 . 1.3245(17) ?
F8 C41 . 1.3261(17) ?
O1 C3 . 1.3366(17) ?
O1 C2 . 1.4849(16) ?
O4 C3 . 1.2071(18) ?
O5 C32 . 1.3319(17) ?
O5 C33 . 1.4816(16) ?
O8 C32 . 1.2087(18) ?
N1 C3 . 1.3875(18) ?
N1 C18 . 1.4198(18) ?
N1 C4 . 1.4557(16) ?
N3 C14 . 1.4905(18) ?
N3 C4 . 1.4934(16) ?
N4 C32 . 1.3825(17) ?
N4 C38 . 1.4201(18) ?
N4 C31 . 1.4597(17) ?
N5 C31 . 1.4870(17) ?
N5 C39 . 1.4875(17) ?
C1 C2 . 1.516(2) ?
C1 H13 . 0.98 ?
C1 H12 . 0.98 ?
C1 H1 . 0.98 ?
C2 C16 . 1.518(2) ?
C2 C17 . 1.520(2) ?
C4 C5 . 1.5716(18) ?
C4 H5 . 1.0 ?
C5 C6 . 1.4667(18) ?
C5 C23 . 1.5155(18) ?
C5 C13 . 1.5373(18) ?
C6 C49 . 1.198(2) ?
C7 C11 . 1.397(2) ?
C7 C8 . 1.399(2) ?
C7 C49 . 1.437(2) ?
C8 C9 . 1.388(2) ?
C8 H22 . 0.95 ?
C9 C10 . 1.378(2) ?
C9 H2 . 0.95 ?
C10 C12 . 1.383(2) ?
C11 C12 . 1.388(2) ?
C11 H3 . 0.95 ?
C12 H4 . 0.95 ?
C13 C14 . 1.5193(19) ?
C13 H20 . 0.99 ?
C13 H21 . 0.99 ?
C14 H18 . 0.99 ?
C14 H19 . 0.99 ?
C16 H8 . 0.98 ?
C16 H7 . 0.98 ?
C16 H6 . 0.98 ?
C17 H9 . 0.98 ?
C17 H10 . 0.98 ?
C17 H11 . 0.98 ?
C18 C19 . 1.3916(19) ?
C18 C23 . 1.3927(19) ?
C19 C20 . 1.397(2) ?
C19 H14 . 0.95 ?
C20 C21 . 1.394(2) ?
C20 H17 . 0.95 ?
C21 C22 . 1.390(2) ?
C21 H16 . 0.95 ?
C22 C23 . 1.384(2) ?
C22 H15 . 0.95 ?
C24 C35 . 1.373(2) ?
C24 C25 . 1.380(2) ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.95 ?
C26 C27 . 1.396(2) ?
C26 H24 . 0.95 ?
C27 C36 . 1.396(2) ?
C27 C28 . 1.434(2) ?
C28 C29 . 1.201(2) ?
C29 C30 . 1.4653(19) ?
C30 C37 . 1.5214(19) ?
C30 C40 . 1.5425(19) ?
C30 C31 . 1.5686(18) ?
C31 H26 . 1.0 ?
C33 C42 . 1.517(2) ?
C33 C34 . 1.518(2) ?
C33 C43 . 1.520(2) ?
C34 H23 . 0.98 ?
C34 H37 . 0.98 ?
C34 H38 . 0.98 ?
C35 C36 . 1.394(2) ?
C35 H44 . 0.95 ?
C36 H43 . 0.95 ?
C37 C47 . 1.386(2) ?
C37 C38 . 1.3921(19) ?
C38 C44 . 1.387(2) ?
C39 C40 . 1.5186(18) ?
C39 H28 . 0.99 ?
C39 H27 . 0.99 ?
C40 H29 . 0.99 ?
C40 H30 . 0.99 ?
C42 H31 . 0.98 ?
C42 H33 . 0.98 ?
C42 H32 . 0.98 ?
C43 H35 . 0.98 ?
C43 H36 . 0.98 ?
C43 H34 . 0.98 ?
C44 C45 . 1.397(2) ?
C44 H39 . 0.95 ?
C45 C46 . 1.389(2) ?
C45 H42 . 0.95 ?
C46 C47 . 1.390(2) ?
C46 H40 . 0.95 ?
C47 H41 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . 121.90(7) ?
O2 S1 N3 . . 110.44(6) ?
O3 S1 N3 . . 110.46(6) ?
O2 S1 C15 . . 104.98(7) ?
O3 S1 C15 . . 103.45(7) ?
N3 S1 C15 . . 103.60(6) ?
O7 S2 O6 . . 122.22(7) ?
O7 S2 N5 . . 110.27(6) ?
O6 S2 N5 . . 110.56(6) ?
O7 S2 C41 . . 104.72(7) ?
O6 S2 C41 . . 103.53(7) ?
N5 S2 C41 . . 103.45(6) ?
C3 O1 C2 . . 121.14(11) ?
C32 O5 C33 . . 120.81(11) ?
C3 N1 C18 . . 123.88(11) ?
C3 N1 C4 . . 125.56(11) ?
C18 N1 C4 . . 109.48(11) ?
C14 N3 C4 . . 112.79(10) ?
C14 N3 S1 . . 122.53(9) ?
C4 N3 S1 . . 123.73(9) ?
C32 N4 C38 . . 123.29(12) ?
C32 N4 C31 . . 125.27(11) ?
C38 N4 C31 . . 109.80(11) ?
C31 N5 C39 . . 112.72(10) ?
C31 N5 S2 . . 123.51(9) ?
C39 N5 S2 . . 122.00(9) ?
C2 C1 H13 . . 109.5 ?
C2 C1 H12 . . 109.5 ?
H13 C1 H12 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H13 C1 H1 . . 109.5 ?
H12 C1 H1 . . 109.5 ?
O1 C2 C1 . . 108.75(11) ?
O1 C2 C16 . . 102.02(11) ?
C1 C2 C16 . . 111.14(13) ?
O1 C2 C17 . . 111.48(12) ?
C1 C2 C17 . . 112.61(14) ?
C16 C2 C17 . . 110.34(13) ?
O4 C3 O1 . . 127.03(13) ?
O4 C3 N1 . . 122.86(13) ?
O1 C3 N1 . . 110.08(11) ?
N1 C4 N3 . . 113.06(10) ?
N1 C4 C5 . . 104.95(10) ?
N3 C4 C5 . . 101.81(10) ?
N1 C4 H5 . . 112.1 ?
N3 C4 H5 . . 112.1 ?
C5 C4 H5 . . 112.1 ?
C6 C5 C23 . . 111.73(11) ?
C6 C5 C13 . . 112.97(11) ?
C23 C5 C13 . . 112.53(11) ?
C6 C5 C4 . . 112.53(11) ?
C23 C5 C4 . . 100.95(10) ?
C13 C5 C4 . . 105.36(10) ?
C49 C6 C5 . . 178.59(15) ?
C11 C7 C8 . . 119.25(13) ?
C11 C7 C49 . . 121.03(13) ?
C8 C7 C49 . . 119.72(13) ?
C9 C8 C7 . . 120.38(14) ?
C9 C8 H22 . . 119.8 ?
C7 C8 H22 . . 119.8 ?
C10 C9 C8 . . 118.52(14) ?
C10 C9 H2 . . 120.7 ?
C8 C9 H2 . . 120.7 ?
F1 C10 C9 . . 118.41(14) ?
F1 C10 C12 . . 118.63(14) ?
C9 C10 C12 . . 122.96(14) ?
C12 C11 C7 . . 120.95(14) ?
C12 C11 H3 . . 119.5 ?
C7 C11 H3 . . 119.5 ?
C10 C12 C11 . . 117.91(14) ?
C10 C12 H4 . . 121.0 ?
C11 C12 H4 . . 121.0 ?
C14 C13 C5 . . 103.55(10) ?
C14 C13 H20 . . 111.1 ?
C5 C13 H20 . . 111.1 ?
C14 C13 H21 . . 111.1 ?
C5 C13 H21 . . 111.1 ?
H20 C13 H21 . . 109.0 ?
N3 C14 C13 . . 101.78(11) ?
N3 C14 H18 . . 111.4 ?
C13 C14 H18 . . 111.4 ?
N3 C14 H19 . . 111.4 ?
C13 C14 H19 . . 111.4 ?
H18 C14 H19 . . 109.3 ?
F2 C15 F3 . . 108.55(12) ?
F2 C15 F4 . . 108.06(12) ?
F3 C15 F4 . . 108.17(12) ?
F2 C15 S1 . . 111.65(10) ?
F3 C15 S1 . . 110.25(10) ?
F4 C15 S1 . . 110.06(10) ?
C2 C16 H8 . . 109.5 ?
C2 C16 H7 . . 109.5 ?
H8 C16 H7 . . 109.5 ?
C2 C16 H6 . . 109.5 ?
H8 C16 H6 . . 109.5 ?
H7 C16 H6 . . 109.5 ?
C2 C17 H9 . . 109.5 ?
C2 C17 H10 . . 109.5 ?
H9 C17 H10 . . 109.5 ?
C2 C17 H11 . . 109.5 ?
H9 C17 H11 . . 109.5 ?
H10 C17 H11 . . 109.5 ?
C19 C18 C23 . . 121.36(13) ?
C19 C18 N1 . . 129.57(12) ?
C23 C18 N1 . . 109.07(12) ?
C18 C19 C20 . . 117.32(13) ?
C18 C19 H14 . . 121.3 ?
C20 C19 H14 . . 121.3 ?
C21 C20 C19 . . 121.60(13) ?
C21 C20 H17 . . 119.2 ?
C19 C20 H17 . . 119.2 ?
C22 C21 C20 . . 120.14(14) ?
C22 C21 H16 . . 119.9 ?
C20 C21 H16 . . 119.9 ?
C23 C22 C21 . . 118.84(14) ?
C23 C22 H15 . . 120.6 ?
C21 C22 H15 . . 120.6 ?
C22 C23 C18 . . 120.73(13) ?
C22 C23 C5 . . 128.22(13) ?
C18 C23 C5 . . 111.04(12) ?
F5 C24 C35 . . 118.90(13) ?
F5 C24 C25 . . 117.48(14) ?
C35 C24 C25 . . 123.63(13) ?
C24 C25 C26 . . 117.99(14) ?
C24 C25 H25 . . 121.0 ?
C26 C25 H25 . . 121.0 ?
C25 C26 C27 . . 120.66(14) ?
C25 C26 H24 . . 119.7 ?
C27 C26 H24 . . 119.7 ?
C26 C27 C36 . . 119.24(13) ?
C26 C27 C28 . . 119.81(13) ?
C36 C27 C28 . . 120.95(14) ?
C29 C28 C27 . . 178.32(16) ?
C28 C29 C30 . . 176.80(15) ?
C29 C30 C37 . . 110.83(12) ?
C29 C30 C40 . . 112.34(11) ?
C37 C30 C40 . . 113.14(11) ?
C29 C30 C31 . . 113.56(11) ?
C37 C30 C31 . . 101.23(10) ?
C40 C30 C31 . . 105.16(10) ?
N4 C31 N5 . . 112.46(10) ?
N4 C31 C30 . . 105.11(10) ?
N5 C31 C30 . . 101.99(10) ?
N4 C31 H26 . . 112.2 ?
N5 C31 H26 . . 112.2 ?
C30 C31 H26 . . 112.2 ?
O8 C32 O5 . . 126.58(13) ?
O8 C32 N4 . . 123.00(13) ?
O5 C32 N4 . . 110.41(12) ?
O5 C33 C42 . . 102.13(11) ?
O5 C33 C34 . . 109.72(11) ?
C42 C33 C34 . . 111.10(13) ?
O5 C33 C43 . . 110.07(12) ?
C42 C33 C43 . . 110.71(14) ?
C34 C33 C43 . . 112.61(14) ?
C33 C34 H23 . . 109.5 ?
C33 C34 H37 . . 109.5 ?
H23 C34 H37 . . 109.5 ?
C33 C34 H38 . . 109.5 ?
H23 C34 H38 . . 109.5 ?
H37 C34 H38 . . 109.5 ?
C24 C35 C36 . . 117.66(14) ?
C24 C35 H44 . . 121.2 ?
C36 C35 H44 . . 121.2 ?
C35 C36 C27 . . 120.82(14) ?
C35 C36 H43 . . 119.6 ?
C27 C36 H43 . . 119.6 ?
C47 C37 C38 . . 120.66(13) ?
C47 C37 C30 . . 128.27(13) ?
C38 C37 C30 . . 111.04(12) ?
C44 C38 C37 . . 121.48(13) ?
C44 C38 N4 . . 129.37(13) ?
C37 C38 N4 . . 109.14(12) ?
N5 C39 C40 . . 101.54(10) ?
N5 C39 H28 . . 111.5 ?
C40 C39 H28 . . 111.5 ?
N5 C39 H27 . . 111.5 ?
C40 C39 H27 . . 111.5 ?
H28 C39 H27 . . 109.3 ?
C39 C40 C30 . . 103.15(10) ?
C39 C40 H29 . . 111.1 ?
C30 C40 H29 . . 111.1 ?
C39 C40 H30 . . 111.1 ?
C30 C40 H30 . . 111.1 ?
H29 C40 H30 . . 109.1 ?
F7 C41 F8 . . 109.05(12) ?
F7 C41 F6 . . 108.39(12) ?
F8 C41 F6 . . 108.03(12) ?
F7 C41 S2 . . 110.25(10) ?
F8 C41 S2 . . 110.98(9) ?
F6 C41 S2 . . 110.08(9) ?
C33 C42 H31 . . 109.5 ?
C33 C42 H33 . . 109.5 ?
H31 C42 H33 . . 109.5 ?
C33 C42 H32 . . 109.5 ?
H31 C42 H32 . . 109.5 ?
H33 C42 H32 . . 109.5 ?
C33 C43 H35 . . 109.5 ?
C33 C43 H36 . . 109.5 ?
H35 C43 H36 . . 109.5 ?
C33 C43 H34 . . 109.5 ?
H35 C43 H34 . . 109.5 ?
H36 C43 H34 . . 109.5 ?
C38 C44 C45 . . 117.28(14) ?
C38 C44 H39 . . 121.4 ?
C45 C44 H39 . . 121.4 ?
C46 C45 C44 . . 121.63(14) ?
C46 C45 H42 . . 119.2 ?
C44 C45 H42 . . 119.2 ?
C45 C46 C47 . . 120.32(13) ?
C45 C46 H40 . . 119.8 ?
C47 C46 H40 . . 119.8 ?
C37 C47 C46 . . 118.61(14) ?
C37 C47 H41 . . 120.7 ?
C46 C47 H41 . . 120.7 ?
C6 C49 C7 . . 178.65(16) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 N3 C14 . . . . -152.40(11) ?
O3 S1 N3 C14 . . . . -14.59(13) ?
C15 S1 N3 C14 . . . . 95.63(12) ?
O2 S1 N3 C4 . . . . 15.61(13) ?
O3 S1 N3 C4 . . . . 153.43(10) ?
C15 S1 N3 C4 . . . . -96.35(11) ?
O7 S2 N5 C31 . . . . -11.09(13) ?
O6 S2 N5 C31 . . . . -149.29(10) ?
C41 S2 N5 C31 . . . . 100.43(11) ?
O7 S2 N5 C39 . . . . 152.68(10) ?
O6 S2 N5 C39 . . . . 14.47(13) ?
C41 S2 N5 C39 . . . . -95.81(11) ?
C3 O1 C2 C1 . . . . -66.85(16) ?
C3 O1 C2 C16 . . . . 175.65(12) ?
C3 O1 C2 C17 . . . . 57.90(17) ?
C2 O1 C3 O4 . . . . -10.4(2) ?
C2 O1 C3 N1 . . . . 171.48(10) ?
C18 N1 C3 O4 . . . . -18.2(2) ?
C4 N1 C3 O4 . . . . 174.94(13) ?
C18 N1 C3 O1 . . . . 160.03(11) ?
C4 N1 C3 O1 . . . . -6.82(18) ?
C3 N1 C4 N3 . . . . -102.44(15) ?
C18 N1 C4 N3 . . . . 89.12(13) ?
C3 N1 C4 C5 . . . . 147.45(12) ?
C18 N1 C4 C5 . . . . -21.00(13) ?
C14 N3 C4 N1 . . . . -107.09(13) ?
S1 N3 C4 N1 . . . . 83.85(14) ?
C14 N3 C4 C5 . . . . 4.95(14) ?
S1 N3 C4 C5 . . . . -164.10(9) ?
N1 C4 C5 C6 . . . . -99.50(12) ?
N3 C4 C5 C6 . . . . 142.47(11) ?
N1 C4 C5 C23 . . . . 19.74(13) ?
N3 C4 C5 C23 . . . . -98.29(11) ?
N1 C4 C5 C13 . . . . 136.99(11) ?
N3 C4 C5 C13 . . . . 18.95(13) ?
C11 C7 C8 C9 . . . . 1.0(2) ?
C49 C7 C8 C9 . . . . -178.59(13) ?
C7 C8 C9 C10 . . . . -0.3(2) ?
C8 C9 C10 F1 . . . . 179.52(13) ?
C8 C9 C10 C12 . . . . -0.4(2) ?
C8 C7 C11 C12 . . . . -1.0(2) ?
C49 C7 C11 C12 . . . . 178.57(14) ?
F1 C10 C12 C11 . . . . -179.54(13) ?
C9 C10 C12 C11 . . . . 0.4(2) ?
C7 C11 C12 C10 . . . . 0.3(2) ?
C6 C5 C13 C14 . . . . -158.92(12) ?
C23 C5 C13 C14 . . . . 73.42(14) ?
C4 C5 C13 C14 . . . . -35.68(13) ?
C4 N3 C14 C13 . . . . -26.85(14) ?
S1 N3 C14 C13 . . . . 142.36(10) ?
C5 C13 C14 N3 . . . . 37.28(13) ?
O2 S1 C15 F2 . . . . -57.17(12) ?
O3 S1 C15 F2 . . . . 174.03(10) ?
N3 S1 C15 F2 . . . . 58.72(12) ?
O2 S1 C15 F3 . . . . 63.58(11) ?
O3 S1 C15 F3 . . . . -65.21(12) ?
N3 S1 C15 F3 . . . . 179.47(10) ?
O2 S1 C15 F4 . . . . -177.17(9) ?
O3 S1 C15 F4 . . . . 54.04(11) ?
N3 S1 C15 F4 . . . . -61.28(11) ?
C3 N1 C18 C19 . . . . 24.5(2) ?
C4 N1 C18 C19 . . . . -166.86(13) ?
C3 N1 C18 C23 . . . . -155.33(12) ?
C4 N1 C18 C23 . . . . 13.35(14) ?
C23 C18 C19 C20 . . . . 0.34(19) ?
N1 C18 C19 C20 . . . . -179.43(13) ?
C18 C19 C20 C21 . . . . -1.0(2) ?
C19 C20 C21 C22 . . . . 0.7(2) ?
C20 C21 C22 C23 . . . . 0.3(2) ?
C21 C22 C23 C18 . . . . -0.9(2) ?
C21 C22 C23 C5 . . . . 178.85(13) ?
C19 C18 C23 C22 . . . . 0.6(2) ?
N1 C18 C23 C22 . . . . -179.58(12) ?
C19 C18 C23 C5 . . . . -179.20(12) ?
N1 C18 C23 C5 . . . . 0.61(15) ?
C6 C5 C23 C22 . . . . -72.73(18) ?
C13 C5 C23 C22 . . . . 55.59(18) ?
C4 C5 C23 C22 . . . . 167.45(13) ?
C6 C5 C23 C18 . . . . 107.06(13) ?
C13 C5 C23 C18 . . . . -124.62(12) ?
C4 C5 C23 C18 . . . . -12.76(14) ?
F5 C24 C25 C26 . . . . -179.28(14) ?
C35 C24 C25 C26 . . . . 0.5(2) ?
C24 C25 C26 C27 . . . . 0.5(2) ?
C25 C26 C27 C36 . . . . -1.0(2) ?
C25 C26 C27 C28 . . . . 178.02(14) ?
C32 N4 C31 N5 . . . . 103.12(14) ?
C38 N4 C31 N5 . . . . -91.14(12) ?
C32 N4 C31 C30 . . . . -146.73(12) ?
C38 N4 C31 C30 . . . . 19.01(13) ?
C39 N5 C31 N4 . . . . 105.74(12) ?
S2 N5 C31 N4 . . . . -89.16(13) ?
C39 N5 C31 C30 . . . . -6.35(14) ?
S2 N5 C31 C30 . . . . 158.75(9) ?
C29 C30 C31 N4 . . . . 100.98(13) ?
C37 C30 C31 N4 . . . . -17.84(12) ?
C40 C30 C31 N4 . . . . -135.81(11) ?
C29 C30 C31 N5 . . . . -141.52(12) ?
C37 C30 C31 N5 . . . . 99.66(11) ?
C40 C30 C31 N5 . . . . -18.30(13) ?
C33 O5 C32 O8 . . . . 3.5(2) ?
C33 O5 C32 N4 . . . . -177.17(11) ?
C38 N4 C32 O8 . . . . 15.2(2) ?
C31 N4 C32 O8 . . . . 179.09(13) ?
C38 N4 C32 O5 . . . . -164.13(12) ?
C31 N4 C32 O5 . . . . -0.22(18) ?
C32 O5 C33 C42 . . . . -178.91(12) ?
C32 O5 C33 C34 . . . . 63.17(17) ?
C32 O5 C33 C43 . . . . -61.29(17) ?
F5 C24 C35 C36 . . . . 178.87(14) ?
C25 C24 C35 C36 . . . . -0.9(2) ?
C24 C35 C36 C27 . . . . 0.3(2) ?
C26 C27 C36 C35 . . . . 0.6(2) ?
C28 C27 C36 C35 . . . . -178.42(14) ?
C29 C30 C37 C47 . . . . 68.45(18) ?
C40 C30 C37 C47 . . . . -58.77(18) ?
C31 C30 C37 C47 . . . . -170.78(14) ?
C29 C30 C37 C38 . . . . -109.19(13) ?
C40 C30 C37 C38 . . . . 123.59(12) ?
C31 C30 C37 C38 . . . . 11.58(14) ?
C47 C37 C38 C44 . . . . 0.8(2) ?
C30 C37 C38 C44 . . . . 178.62(12) ?
C47 C37 C38 N4 . . . . -178.40(12) ?
C30 C37 C38 N4 . . . . -0.56(15) ?
C32 N4 C38 C44 . . . . -25.1(2) ?
C31 N4 C38 C44 . . . . 168.85(13) ?
C32 N4 C38 C37 . . . . 154.02(12) ?
C31 N4 C38 C37 . . . . -12.06(14) ?
C31 N5 C39 C40 . . . . 28.53(14) ?
S2 N5 C39 C40 . . . . -136.83(10) ?
N5 C39 C40 C30 . . . . -38.29(13) ?
C29 C30 C40 C39 . . . . 159.85(12) ?
C37 C30 C40 C39 . . . . -73.73(13) ?
C31 C30 C40 C39 . . . . 35.86(13) ?
O7 S2 C41 F7 . . . . -69.96(11) ?
O6 S2 C41 F7 . . . . 59.11(11) ?
N5 S2 C41 F7 . . . . 174.51(10) ?
O7 S2 C41 F8 . . . . 50.97(11) ?
O6 S2 C41 F8 . . . . -179.96(10) ?
N5 S2 C41 F8 . . . . -64.56(11) ?
O7 S2 C41 F6 . . . . 170.52(10) ?
O6 S2 C41 F6 . . . . -60.41(11) ?
N5 S2 C41 F6 . . . . 54.98(11) ?
C37 C38 C44 C45 . . . . -1.5(2) ?
N4 C38 C44 C45 . . . . 177.55(13) ?
C38 C44 C45 C46 . . . . 1.1(2) ?
C44 C45 C46 C47 . . . . -0.2(2) ?
C38 C37 C47 C46 . . . . 0.3(2) ?
C30 C37 C47 C46 . . . . -177.18(13) ?
C45 C46 C47 C37 . . . . -0.6(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 O4 . 0.98 2.63 3.172(2) 115.3 ?
C12 H4 O8 1_565 0.95 2.50 3.4315(18) 166.5 ?
C13 H20 F1 2_676 0.99 2.61 3.3039(17) 127.1 ?
C13 H20 O7 2_676 0.99 2.48 3.2664(18) 135.8 ?
C17 H9 O4 . 0.98 2.40 2.931(2) 113.3 ?
C17 H10 F4 1_655 0.98 2.57 3.3447(18) 136.2 ?
C19 H14 O4 . 0.95 2.43 2.9310(18) 112.8 ?
C34 H23 O8 . 0.98 2.46 3.047(2) 117.9 ?
C40 H30 F5 2_765 0.99 2.51 3.2486(17) 130.8 ?
C43 H36 F6 1_455 0.98 2.58 3.4390(19) 146.3 ?
C43 H34 O8 . 0.98 2.41 2.972(2) 115.7 ?
C44 H39 O8 . 0.95 2.41 2.9027(18) 111.7 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetate/petroleum ether'
