# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_SS-02-177_a
_audit_block_doi                 10.5517/ccdc.csd.cc1zq494
_database_code_depnum_ccdc_archive 'CCDC 1838526'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 F3 N3 O3 S, 2(C2 H6 O S)'
_chemical_formula_sum            'C25 H26 F3 N3 O5 S3'
_chemical_formula_weight         601.67

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'
F F 0.0171 0.0103 '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'
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                   19.508(2)
_cell_length_b                   8.2786(10)
_cell_length_c                   17.511(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.363(3)
_cell_angle_gamma                90
_cell_volume                     2713.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6019
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             1248.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45772
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.088
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6778
_reflns_number_gt                5033
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.3827P] 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         6763
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_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
S2 S 0.38262(3) 0.82434(5) 0.58495(3) 0.01750(13) Uani 1 1 d . . . . .
S3 S 0.08970(3) 0.88834(6) -0.00682(3) 0.02200(14) Uani 1 1 d . . . . .
S1 S 0.34069(3) 0.33737(6) 0.41951(4) 0.02741(15) Uani 1 1 d . . . . .
F1 F 0.21144(7) 0.53608(16) 0.38096(9) 0.0368(4) Uani 1 1 d . . . . .
F3 F 0.33523(8) 0.17571(16) 0.25851(10) 0.0407(4) Uani 1 1 d . . . . .
O1 O 0.26886(8) 0.80169(17) 0.20676(9) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.08525(8) 0.97360(19) 0.06770(9) 0.0277(4) Uani 1 1 d . . . . .
O4 O 0.32949(8) 0.78172(18) 0.50616(9) 0.0239(3) Uani 1 1 d . . . . .
N1 N 0.15145(8) 0.96273(18) 0.23178(10) 0.0164(3) Uani 1 1 d . . . . .
H1 H 0.143364 0.931630 0.183191 0.020 Uiso 1 1 calc R U . . .
N2 N 0.32166(9) 0.78538(19) 0.34064(10) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.314629 0.799177 0.386524 0.021 Uiso 1 1 calc R U . . .
F2 F 0.12074(10) 0.4043(2) 0.11244(11) 0.0632(6) Uani 1 1 d . . . . .
O3 O 0.39370(9) 0.22669(18) 0.41076(12) 0.0401(5) Uani 1 1 d . . . . .
O2 O 0.30397(10) 0.3090(2) 0.47832(11) 0.0410(5) Uani 1 1 d . . . . .
N3 N 0.37636(9) 0.5152(2) 0.43798(11) 0.0221(4) Uani 1 1 d . . . . .
H3 H 0.371917 0.568632 0.478444 0.027 Uiso 1 1 calc R U . . .
C1 C 0.10740(10) 1.0595(2) 0.26088(12) 0.0162(4) Uani 1 1 d . . . . .
C9 C 0.26891(11) 0.8322(2) 0.27554(12) 0.0169(4) Uani 1 1 d . . . . .
C8 C 0.21044(10) 0.9238(2) 0.29297(12) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.04254(11) 1.1312(2) 0.22048(13) 0.0200(4) Uani 1 1 d . . . . .
H2A H 0.022271 1.115619 0.166190 0.024 Uiso 1 1 calc R U . . .
C10 C 0.38719(10) 0.7157(2) 0.33843(12) 0.0167(4) Uani 1 1 d . . . . .
C7 C 0.20471(11) 0.9931(2) 0.36276(12) 0.0177(4) Uani 1 1 d . . . . .
H7 H 0.237325 0.984271 0.412842 0.021 Uiso 1 1 calc R U . . .
C6 C 0.13924(11) 1.0806(2) 0.34316(12) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.41514(11) 0.5845(2) 0.38776(12) 0.0184(4) Uani 1 1 d . . . . .
C14 C 0.48221(11) 0.5234(2) 0.38962(13) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.501575 0.438800 0.423852 0.028 Uiso 1 1 calc R U . . .
C3 C 0.01003(11) 1.2258(2) 0.26454(14) 0.0239(5) Uani 1 1 d . . . . .
H3A H -0.033300 1.275057 0.239385 0.029 Uiso 1 1 calc R U . . .
C13 C 0.52011(11) 0.5876(3) 0.34098(14) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.564703 0.545933 0.342349 0.030 Uiso 1 1 calc R U . . .
C11 C 0.42578(11) 0.7797(2) 0.28952(13) 0.0200(4) Uani 1 1 d . . . . .
H11 H 0.407389 0.866537 0.256367 0.024 Uiso 1 1 calc R U . . .
C12 C 0.49153(11) 0.7146(3) 0.29000(13) 0.0234(4) Uani 1 1 d . . . . .
H12 H 0.516426 0.755936 0.256222 0.028 Uiso 1 1 calc R U . . .
C16 C 0.27625(11) 0.3542(2) 0.32534(14) 0.0228(4) Uani 1 1 d . . . . .
C5 C 0.10428(12) 1.1790(2) 0.38659(14) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.123933 1.195304 0.440920 0.028 Uiso 1 1 calc R U . . .
C4 C 0.04037(12) 1.2503(2) 0.34653(14) 0.0245(5) Uani 1 1 d . . . . .
H4 H 0.016921 1.315717 0.374301 0.029 Uiso 1 1 calc R U . . .
C17 C 0.21683(11) 0.4532(2) 0.31672(15) 0.0260(5) Uani 1 1 d . . . . .
C21 C 0.27943(12) 0.2725(2) 0.25701(15) 0.0286(5) Uani 1 1 d . . . . .
C23 C 0.34209(12) 0.9832(2) 0.62569(14) 0.0250(5) Uani 1 1 d . . . . .
H23A H 0.326765 1.067090 0.586729 0.037 Uiso 1 1 calc R U . . .
H23B H 0.376095 1.026428 0.671956 0.037 Uiso 1 1 calc R U . . .
H23C H 0.301588 0.941736 0.640293 0.037 Uiso 1 1 calc R U . . .
C22 C 0.45002(12) 0.9403(3) 0.55996(15) 0.0286(5) Uani 1 1 d . . . . .
H22A H 0.474397 0.874104 0.530903 0.043 Uiso 1 1 calc R U . . .
H22B H 0.483568 0.978621 0.607787 0.043 Uiso 1 1 calc R U . . .
H22C H 0.428461 1.030650 0.527725 0.043 Uiso 1 1 calc R U . . .
C18 C 0.16376(12) 0.4725(3) 0.24692(17) 0.0366(6) Uani 1 1 d . . . . .
H18 H 0.124761 0.539698 0.243285 0.044 Uiso 1 1 calc R U . . .
C25 C 0.03586(14) 0.7115(3) -0.01508(15) 0.0321(5) Uani 1 1 d . . . . .
H25A H 0.051003 0.650391 0.033361 0.048 Uiso 1 1 calc R U . . .
H25B H 0.040857 0.646757 -0.058671 0.048 Uiso 1 1 calc R U . . .
H25C H -0.013264 0.742224 -0.024365 0.048 Uiso 1 1 calc R U . . .
C19 C 0.17147(14) 0.3868(3) 0.18255(16) 0.0397(7) Uani 1 1 d . . . . .
C20 C 0.22769(14) 0.2859(3) 0.18537(16) 0.0369(6) Uani 1 1 d . . . . .
H20 H 0.230783 0.228843 0.140724 0.044 Uiso 1 1 calc R U . . .
C24 C 0.17462(14) 0.7911(4) 0.01874(17) 0.0443(7) Uani 1 1 d . . . . .
H24A H 0.211652 0.871083 0.027253 0.066 Uiso 1 1 calc R U . . .
H24B H 0.177512 0.720651 -0.023773 0.066 Uiso 1 1 calc R U . . .
H24C H 0.180445 0.729275 0.066523 0.066 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
S2 O4 1.5154(15) . ?
S2 C22 1.779(2) . ?
S2 C23 1.784(2) . ?
S3 O5 1.5075(16) . ?
S3 C24 1.782(2) . ?
S3 C25 1.784(2) . ?
S1 O3 1.4218(18) . ?
S1 O2 1.4299(19) . ?
S1 N3 1.6218(17) . ?
S1 C16 1.775(2) . ?
F1 C17 1.347(3) . ?
F3 C21 1.346(3) . ?
O1 C9 1.230(3) . ?
N1 C8 1.372(2) . ?
N1 C1 1.374(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.359(3) . ?
N2 C10 1.413(2) . ?
N2 H2 0.8600 . ?
F2 C19 1.350(3) . ?
N3 C15 1.431(3) . ?
N3 H3 0.8600 . ?
C1 C2 1.396(3) . ?
C1 C6 1.410(3) . ?
C9 C8 1.472(3) . ?
C8 C7 1.383(3) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C10 C11 1.394(3) . ?
C10 C15 1.400(3) . ?
C7 C6 1.423(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.414(3) . ?
C15 C14 1.394(3) . ?
C14 C13 1.382(3) . ?
C14 H14 0.9300 . ?
C3 C4 1.405(3) . ?
C3 H3A 0.9300 . ?
C13 C12 1.390(3) . ?
C13 H13 0.9300 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.392(3) . ?
C16 C21 1.391(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C17 C18 1.371(3) . ?
C21 C20 1.375(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C19 C20 1.368(4) . ?
C20 H20 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 S2 C22 105.37(10) . . ?
O4 S2 C23 105.62(10) . . ?
C22 S2 C23 98.17(10) . . ?
O5 S3 C24 105.68(11) . . ?
O5 S3 C25 106.15(11) . . ?
C24 S3 C25 97.72(14) . . ?
O3 S1 O2 119.93(11) . . ?
O3 S1 N3 108.81(10) . . ?
O2 S1 N3 106.22(11) . . ?
O3 S1 C16 107.26(11) . . ?
O2 S1 C16 108.33(11) . . ?
N3 S1 C16 105.41(9) . . ?
C8 N1 C1 108.79(17) . . ?
C8 N1 H1 125.6 . . ?
C1 N1 H1 125.6 . . ?
C9 N2 C10 124.78(17) . . ?
C9 N2 H2 117.6 . . ?
C10 N2 H2 117.6 . . ?
C15 N3 S1 120.82(15) . . ?
C15 N3 H3 119.6 . . ?
S1 N3 H3 119.6 . . ?
N1 C1 C2 129.21(19) . . ?
N1 C1 C6 108.03(17) . . ?
C2 C1 C6 122.75(18) . . ?
O1 C9 N2 123.65(18) . . ?
O1 C9 C8 121.46(18) . . ?
N2 C9 C8 114.89(17) . . ?
N1 C8 C7 109.51(17) . . ?
N1 C8 C9 119.19(17) . . ?
C7 C8 C9 131.11(19) . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2A 121.5 . . ?
C1 C2 H2A 121.5 . . ?
C11 C10 C15 119.35(18) . . ?
C11 C10 N2 120.73(17) . . ?
C15 C10 N2 119.88(18) . . ?
C8 C7 C6 106.76(18) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C1 C6 C7 106.90(17) . . ?
C1 C6 C5 118.71(19) . . ?
C7 C6 C5 134.4(2) . . ?
C14 C15 C10 119.72(19) . . ?
C14 C15 N3 119.68(18) . . ?
C10 C15 N3 120.57(18) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C14 C13 C12 119.96(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C10 C11 C12 120.40(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C17 C16 C21 115.5(2) . . ?
C17 C16 S1 119.80(18) . . ?
C21 C16 S1 124.70(17) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C4 C3 121.23(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
F1 C17 C18 117.9(2) . . ?
F1 C17 C16 117.9(2) . . ?
C18 C17 C16 124.2(2) . . ?
F3 C21 C20 116.6(2) . . ?
F3 C21 C16 120.3(2) . . ?
C20 C21 C16 123.1(2) . . ?
S2 C23 H23A 109.5 . . ?
S2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C18 C19 116.2(2) . . ?
C17 C18 H18 121.9 . . ?
C19 C18 H18 121.9 . . ?
S3 C25 H25A 109.5 . . ?
S3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F2 C19 C20 118.2(3) . . ?
F2 C19 C18 118.0(3) . . ?
C20 C19 C18 123.8(2) . . ?
C19 C20 C21 117.2(3) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
S3 C24 H24A 109.5 . . ?
S3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc1zsb69
_database_code_depnum_ccdc_archive 'CCDC 1840631'
_audit_update_record             
;
2018-04-30 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N4 O5 S, C2 H6 O S'
_chemical_formula_sum            'C23 H22 N4 O6 S2'
_chemical_formula_weight         514.56

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'
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                   7.567(2)
_cell_length_b                   12.628(4)
_cell_length_c                   12.890(4)
_cell_angle_alpha                106.657(6)
_cell_angle_beta                 91.327(7)
_cell_angle_gamma                92.275(7)
_cell_volume                     1178.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4528
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.951
_exptl_transmission_factor_max   0.943
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21482
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.650
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5854
_reflns_number_gt                4117
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.0198P] 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         5854
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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 0.01982(8) 0.20355(5) 0.64780(5) 0.01661(16) Uani 1 1 d . . . . .
S2 S 0.55764(8) 0.10819(5) 0.43289(5) 0.01679(16) Uani 1 1 d . . . . .
O1 O 0.4808(2) 0.36197(14) 0.94330(14) 0.0196(4) Uani 1 1 d . . . . .
O2 O -0.1240(2) 0.17518(14) 0.70677(15) 0.0218(4) Uani 1 1 d . . . . .
O4 O 0.3578(3) 0.72177(15) 0.84116(15) 0.0257(4) Uani 1 1 d . . . . .
O3 O -0.0058(2) 0.20133(14) 0.53628(15) 0.0231(4) Uani 1 1 d . . . . .
O6 O 0.4881(2) 0.15115(15) 0.54568(14) 0.0231(4) Uani 1 1 d . . . . .
O5 O 0.1864(2) 0.71168(15) 0.97165(15) 0.0266(4) Uani 1 1 d . . . . .
N1 N 0.6558(3) 0.51537(15) 0.86126(16) 0.0149(4) Uani 1 1 d . . . . .
H1 H 0.636419 0.540409 0.929208 0.018 Uiso 1 1 calc R U . . .
N2 N 0.4780(3) 0.22958(16) 0.78056(16) 0.0154(4) Uani 1 1 d . . . . .
H2 H 0.515360 0.211874 0.715609 0.018 Uiso 1 1 calc R U . . .
N3 N 0.1787(3) 0.12113(16) 0.65031(16) 0.0161(4) Uani 1 1 d . . . . .
H3 H 0.234650 0.092256 0.592455 0.019 Uiso 1 1 calc R U . . .
N4 N 0.2553(3) 0.67076(17) 0.88449(17) 0.0192(5) Uani 1 1 d . . . . .
C8 C 0.6144(3) 0.40864(18) 0.79707(19) 0.0140(5) Uani 1 1 d . . . . .
C16 C 0.0999(3) 0.34021(19) 0.7199(2) 0.0159(5) Uani 1 1 d . . . . .
C5 C 0.7420(3) 0.50285(19) 0.69194(19) 0.0156(5) Uani 1 1 d . . . . .
C19 C 0.2086(3) 0.55302(19) 0.8269(2) 0.0160(5) Uani 1 1 d . . . . .
C6 C 0.7328(3) 0.57463(19) 0.79902(19) 0.0149(5) Uani 1 1 d . . . . .
C10 C 0.3733(3) 0.15004(18) 0.81360(19) 0.0142(5) Uani 1 1 d . . . . .
C9 C 0.5216(3) 0.33206(19) 0.84680(19) 0.0142(5) Uani 1 1 d . . . . .
C21 C 0.1902(3) 0.4041(2) 0.6648(2) 0.0177(5) Uani 1 1 d . . . . .
H21 H 0.213439 0.374283 0.591987 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6665(3) 0.39801(19) 0.69326(19) 0.0150(5) Uani 1 1 d . . . . .
H7 H 0.654767 0.334378 0.634849 0.018 Uiso 1 1 calc R U . . .
C15 C 0.2253(3) 0.09663(18) 0.74952(19) 0.0144(5) Uani 1 1 d . . . . .
C11 C 0.4150(3) 0.12398(19) 0.9093(2) 0.0187(5) Uani 1 1 d . . . . .
H11 H 0.514202 0.157911 0.951467 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0712(3) 0.3809(2) 0.8305(2) 0.0191(5) Uani 1 1 d . . . . .
H17 H 0.015664 0.336192 0.867351 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8204(3) 0.5442(2) 0.6119(2) 0.0186(5) Uani 1 1 d . . . . .
H4A H 0.828154 0.498905 0.541303 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8738(3) 0.7221(2) 0.7477(2) 0.0214(5) Uani 1 1 d . . . . .
H2A H 0.918802 0.794838 0.764696 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7984(3) 0.6847(2) 0.8272(2) 0.0197(5) Uani 1 1 d . . . . .
H1A H 0.791048 0.730929 0.897417 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2457(3) 0.5124(2) 0.7185(2) 0.0184(5) Uani 1 1 d . . . . .
H20 H 0.305903 0.556379 0.682749 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1218(3) 0.0185(2) 0.7816(2) 0.0194(5) Uani 1 1 d . . . . .
H14 H 0.025325 -0.017863 0.738122 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8849(3) 0.6524(2) 0.6402(2) 0.0217(5) Uani 1 1 d . . . . .
H3A H 0.936493 0.680331 0.588125 0.026 Uiso 1 1 calc R U . . .
C18 C 0.1269(3) 0.4892(2) 0.8845(2) 0.0197(5) Uani 1 1 d . . . . .
H18 H 0.109401 0.518266 0.958175 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3095(4) 0.0479(2) 0.9418(2) 0.0226(6) Uani 1 1 d . . . . .
H12 H 0.336890 0.032198 1.006376 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1613(3) -0.0055(2) 0.8777(2) 0.0227(6) Uani 1 1 d . . . . .
H13 H 0.090376 -0.056554 0.899484 0.027 Uiso 1 1 calc R U . . .
C23 C 0.6178(4) 0.2279(2) 0.3920(2) 0.0279(6) Uani 1 1 d . . . . .
H23A H 0.519206 0.274772 0.399865 0.042 Uiso 1 1 calc R U . . .
H23B H 0.650398 0.205723 0.317597 0.042 Uiso 1 1 calc R U . . .
H23C H 0.716259 0.267626 0.436569 0.042 Uiso 1 1 calc R U . . .
C22 C 0.3647(4) 0.0633(2) 0.3463(2) 0.0266(6) Uani 1 1 d . . . . .
H22A H 0.315001 -0.004051 0.356413 0.040 Uiso 1 1 calc R U . . .
H22B H 0.396246 0.050522 0.272190 0.040 Uiso 1 1 calc R U . . .
H22C H 0.279131 0.119288 0.363887 0.040 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 1.4329(19) . ?
S1 O3 1.4382(19) . ?
S1 N3 1.627(2) . ?
S1 C16 1.783(2) . ?
S2 O6 1.5136(18) . ?
S2 C23 1.784(3) . ?
S2 C22 1.787(3) . ?
O1 C9 1.242(3) . ?
O4 N4 1.231(3) . ?
O5 N4 1.231(3) . ?
N1 C6 1.369(3) . ?
N1 C8 1.384(3) . ?
N1 H1 0.8600 . ?
N2 C9 1.354(3) . ?
N2 C10 1.420(3) . ?
N2 H2 0.8600 . ?
N3 C15 1.439(3) . ?
N3 H3 0.8600 . ?
N4 C19 1.483(3) . ?
C8 C7 1.375(3) . ?
C8 C9 1.470(3) . ?
C16 C21 1.388(3) . ?
C16 C17 1.395(3) . ?
C5 C4 1.414(3) . ?
C5 C6 1.423(3) . ?
C5 C7 1.426(3) . ?
C19 C18 1.381(3) . ?
C19 C20 1.383(3) . ?
C6 C1 1.399(3) . ?
C10 C11 1.397(3) . ?
C10 C15 1.403(3) . ?
C21 C20 1.387(3) . ?
C21 H21 0.9300 . ?
C7 H7 0.9300 . ?
C15 C14 1.395(3) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C4 C3 1.376(4) . ?
C4 H4A 0.9300 . ?
C2 C1 1.371(4) . ?
C2 C3 1.419(4) . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
C20 H20 0.9300 . ?
C14 C13 1.385(4) . ?
C14 H14 0.9300 . ?
C3 H3A 0.9300 . ?
C18 H18 0.9300 . ?
C12 C13 1.405(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 O3 120.62(11) . . ?
O2 S1 N3 108.21(11) . . ?
O3 S1 N3 106.02(11) . . ?
O2 S1 C16 107.21(11) . . ?
O3 S1 C16 106.88(11) . . ?
N3 S1 C16 107.24(10) . . ?
O6 S2 C23 105.76(12) . . ?
O6 S2 C22 104.92(12) . . ?
C23 S2 C22 98.01(13) . . ?
C6 N1 C8 108.9(2) . . ?
C6 N1 H1 125.5 . . ?
C8 N1 H1 125.5 . . ?
C9 N2 C10 122.9(2) . . ?
C9 N2 H2 118.6 . . ?
C10 N2 H2 118.6 . . ?
C15 N3 S1 119.87(16) . . ?
C15 N3 H3 120.1 . . ?
S1 N3 H3 120.1 . . ?
O4 N4 O5 124.2(2) . . ?
O4 N4 C19 117.9(2) . . ?
O5 N4 C19 117.8(2) . . ?
C7 C8 N1 109.4(2) . . ?
C7 C8 C9 132.6(2) . . ?
N1 C8 C9 117.9(2) . . ?
C21 C16 C17 121.2(2) . . ?
C21 C16 S1 119.31(19) . . ?
C17 C16 S1 119.46(18) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 C7 134.4(2) . . ?
C6 C5 C7 106.7(2) . . ?
C18 C19 C20 122.9(2) . . ?
C18 C19 N4 117.9(2) . . ?
C20 C19 N4 119.1(2) . . ?
N1 C6 C1 130.2(2) . . ?
N1 C6 C5 107.8(2) . . ?
C1 C6 C5 122.0(2) . . ?
C11 C10 C15 119.2(2) . . ?
C11 C10 N2 121.1(2) . . ?
C15 C10 N2 119.7(2) . . ?
O1 C9 N2 122.5(2) . . ?
O1 C9 C8 121.3(2) . . ?
N2 C9 C8 116.2(2) . . ?
C20 C21 C16 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C8 C7 C5 107.1(2) . . ?
C8 C7 H7 126.4 . . ?
C5 C7 H7 126.4 . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 N3 119.2(2) . . ?
C10 C15 N3 120.8(2) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 H1A 121.2 . . ?
C6 C1 H1A 121.2 . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
S2 C23 H23A 109.5 . . ?
S2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.096



####################################################################### 
# 
# 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_TRIAL1_a
_audit_block_doi                 10.5517/ccdc.csd.cc1zls4h
_database_code_depnum_ccdc_archive 'CCDC 1835297'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H52 Cl F3 N4 O4.50 S'
_chemical_formula_weight         761.34

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'
Cl Cl 0.1484 0.1585 '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'
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'
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           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                   20.234(4)
_cell_length_b                   13.246(2)
_cell_length_c                   30.365(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.943(5)
_cell_angle_gamma                90
_cell_volume                     7963(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      23.94

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             3232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38339
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.371
_diffrn_reflns_theta_max         25.086
_diffrn_reflns_theta_full        25.086
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7067
_reflns_number_gt                4668
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1503P)²+28.5096P] 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         7067
_refine_ls_number_parameters     469
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2830
_refine_ls_wR_factor_gt          0.2478
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.053
_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 0.55950(6) 0.11045(9) 0.37180(5) 0.0520(4) Uani 1 1 d . . . . .
Cl1 Cl 0.63108(6) 0.24482(10) 0.19124(5) 0.0593(4) Uani 1 1 d . . . . .
O1 O 0.47725(17) 0.3668(2) 0.48002(11) 0.0484(8) Uani 1 1 d . . . . .
N3 N 0.48736(17) 0.5460(2) 0.43338(12) 0.0374(8) Uani 1 1 d . . . . .
H16 H 0.492006 0.556528 0.461803 0.045 Uiso 1 1 calc R U . . .
O3 O 0.56640(18) 0.1265(3) 0.32630(14) 0.0683(11) Uani 1 1 d . . . . .
N2 N 0.43714(17) 0.2830(3) 0.41431(13) 0.0366(8) Uani 1 1 d . . . . .
H10 H 0.423869 0.290219 0.385692 0.044 Uiso 1 1 calc R U . . .
N1 N 0.47983(17) 0.1170(3) 0.37063(14) 0.0428(9) Uani 1 1 d . . . . .
H5 H 0.452518 0.129096 0.345487 0.051 Uiso 1 1 calc R U . . .
O2 O 0.58593(18) 0.0210(3) 0.39504(17) 0.0732(12) Uani 1 1 d . . . . .
N4 N 0.24228(18) 0.0350(3) 0.18793(15) 0.0488(10) Uani 1 1 d . . . . .
C17 C 0.4849(2) 0.5689(3) 0.35940(15) 0.0372(10) Uani 1 1 d . . . . .
C15 C 0.4683(2) 0.4560(3) 0.41172(15) 0.0363(10) Uani 1 1 d . . . . .
C16 C 0.4661(2) 0.4671(3) 0.36645(15) 0.0364(10) Uani 1 1 d . . . . .
H11 H 0.454572 0.417631 0.344479 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4609(2) 0.3658(3) 0.43856(15) 0.0351(9) Uani 1 1 d . . . . .
C22 C 0.4977(2) 0.6156(3) 0.40246(15) 0.0370(10) Uani 1 1 d . . . . .
C9 C 0.4324(2) 0.1857(3) 0.43233(16) 0.0395(10) Uani 1 1 d . . . . .
C5 C 0.5987(2) 0.2127(3) 0.40432(18) 0.0441(11) Uani 1 1 d . . . . .
C18 C 0.4928(2) 0.6238(4) 0.32175(17) 0.0470(11) Uani 1 1 d . . . . .
H12 H 0.485158 0.594035 0.293412 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4065(2) 0.1700(4) 0.47088(17) 0.0472(11) Uani 1 1 d . . . . .
H6 H 0.391701 0.224553 0.485583 0.057 Uiso 1 1 calc R U . . .
C21 C 0.5167(2) 0.7171(3) 0.40791(17) 0.0444(11) Uani 1 1 d . . . . .
H15 H 0.524207 0.748129 0.435984 0.053 Uiso 1 1 calc R U . . .
C20 C 0.5238(2) 0.7689(4) 0.37008(19) 0.0520(13) Uani 1 1 d . . . . .
H14 H 0.536868 0.836284 0.372754 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4531(2) 0.1031(3) 0.41038(17) 0.0424(11) Uani 1 1 d . . . . .
C27 C 0.2192(2) -0.0479(4) 0.15344(19) 0.0536(13) Uani 1 1 d . . . . .
H26 H 0.211038 -0.108456 0.169499 0.064 Uiso 1 1 calc R U . . .
H27 H 0.176262 -0.027628 0.134868 0.064 Uiso 1 1 calc R U . . .
C19 C 0.5121(2) 0.7235(4) 0.32759(19) 0.0523(13) Uani 1 1 d . . . . .
H13 H 0.517462 0.761338 0.302773 0.063 Uiso 1 1 calc R U . . .
C35 C 0.1903(2) 0.0410(4) 0.21740(18) 0.0548(13) Uani 1 1 d . . . . .
H45 H 0.147230 0.059522 0.198567 0.066 Uiso 1 1 calc R U . . .
H44 H 0.185192 -0.025826 0.229335 0.066 Uiso 1 1 calc R U . . .
C31 C 0.2477(2) 0.1357(4) 0.1641(2) 0.0539(13) Uani 1 1 d . . . . .
H36 H 0.263542 0.186427 0.186911 0.065 Uiso 1 1 calc R U . . .
H35 H 0.281770 0.128779 0.146107 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4475(3) 0.0063(4) 0.4263(2) 0.0599(14) Uani 1 1 d . . . . .
H9 H 0.460054 -0.049037 0.411047 0.072 Uiso 1 1 calc R U . . .
C4 C 0.5989(2) 0.3073(4) 0.3851(2) 0.0555(13) Uani 1 1 d . . . . .
H3 H 0.580035 0.317125 0.354748 0.067 Uiso 1 1 calc R U . . .
C28 C 0.2664(3) -0.0748(4) 0.1227(2) 0.0625(15) Uani 1 1 d . . . . .
H28 H 0.309563 -0.096590 0.140406 0.075 Uiso 1 1 calc R U . . .
H29 H 0.274059 -0.016078 0.105326 0.075 Uiso 1 1 calc R U . . .
C26 C 0.3120(2) 0.0128(4) 0.2161(2) 0.0605(15) Uani 1 1 d . . . . .
H24 H 0.344026 0.011008 0.196318 0.073 Uiso 1 1 calc R U . . .
H25 H 0.324982 0.067844 0.237146 0.073 Uiso 1 1 calc R U . . .
C11 C 0.4027(3) 0.0726(4) 0.4873(2) 0.0598(14) Uani 1 1 d . . . . .
H7 H 0.386418 0.062050 0.513369 0.072 Uiso 1 1 calc R U . . .
C32 C 0.1837(3) 0.1740(4) 0.1342(2) 0.0616(14) Uani 1 1 d . . . . .
H38 H 0.151285 0.191143 0.152463 0.074 Uiso 1 1 calc R U . . .
H37 H 0.164226 0.121084 0.113443 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6273(3) 0.1977(4) 0.4489(2) 0.0642(15) Uani 1 1 d . . . . .
H2 H 0.627581 0.133617 0.461450 0.077 Uiso 1 1 calc R U . . .
F2 F 0.6678(4) 0.5447(4) 0.4705(3) 0.189(4) Uani 1 1 d . . . . .
C25 C 0.3171(3) -0.0851(5) 0.2421(2) 0.0667(15) Uani 1 1 d . U . . .
H22 H 0.291723 -0.078613 0.265765 0.080 Uiso 1 1 calc R U . . .
H23 H 0.296342 -0.138409 0.222014 0.080 Uiso 1 1 calc R U . . .
F1 F 0.7478(3) 0.4586(5) 0.4946(3) 0.211(4) Uani 1 1 d . . . . .
C12 C 0.4229(3) -0.0073(4) 0.4651(2) 0.0716(17) Uani 1 1 d . . . . .
H8 H 0.420056 -0.072180 0.476283 0.086 Uiso 1 1 calc R U . . .
C33 C 0.1971(3) 0.2668(4) 0.1075(2) 0.0713(17) Uani 1 1 d . . . . .
H39 H 0.232225 0.250523 0.091277 0.086 Uiso 1 1 calc R U . . .
H40 H 0.156389 0.282292 0.085401 0.086 Uiso 1 1 calc R U . . .
C29 C 0.2351(3) -0.1597(5) 0.0909(2) 0.0713(16) Uani 1 1 d . . . . .
H30 H 0.222251 -0.214468 0.108658 0.086 Uiso 1 1 calc R U . . .
H31 H 0.194277 -0.134670 0.071382 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6555(3) 0.2775(5) 0.4750(2) 0.0745(18) Uani 1 1 d . . . . .
H1 H 0.675144 0.267174 0.505120 0.089 Uiso 1 1 calc R U . . .
F3 F 0.6665(5) 0.4620(6) 0.5231(3) 0.239(5) Uani 1 1 d . . . . .
C30 C 0.2810(3) -0.2002(6) 0.0625(3) 0.091(2) Uani 1 1 d . . . . .
H33 H 0.292846 -0.146984 0.044111 0.137 Uiso 1 1 calc R U . . .
H34 H 0.258585 -0.253232 0.043651 0.137 Uiso 1 1 calc R U . . .
H32 H 0.321256 -0.226279 0.081581 0.137 Uiso 1 1 calc R U . . .
C36 C 0.2054(3) 0.1127(8) 0.2556(3) 0.116(3) Uani 1 1 d . . . . .
H46 H 0.199149 0.181361 0.244362 0.139 Uiso 1 1 calc R U . . .
H47 H 0.252086 0.105095 0.271104 0.139 Uiso 1 1 calc R U . . .
C34 C 0.2172(4) 0.3559(5) 0.1346(3) 0.096(2) Uani 1 1 d . . . . .
H43 H 0.183876 0.370828 0.151992 0.144 Uiso 1 1 calc R U . . .
H42 H 0.221142 0.411985 0.115265 0.144 Uiso 1 1 calc R U . . .
H41 H 0.259992 0.343918 0.154418 0.144 Uiso 1 1 calc R U . . .
C24 C 0.3859(4) -0.1146(7) 0.2622(4) 0.119(3) Uani 1 1 d . U . . .
H21 H 0.384231 -0.170539 0.282515 0.142 Uiso 1 1 calc R U . . .
H20 H 0.407411 -0.138882 0.238455 0.142 Uiso 1 1 calc R U . . .
O4 O 0.6049(5) 0.3014(7) 0.2792(3) 0.188(3) Uani 1 1 d . U . . .
O5 O 0.500000 0.4269(13) 0.250000 0.232(6) Uani 1 2 d S TU P . .
C37 C 0.1584(4) 0.0930(10) 0.2887(3) 0.153(5) Uani 1 1 d . . . . .
H49 H 0.115171 0.124303 0.276577 0.183 Uiso 1 1 calc R U . . .
H48 H 0.150839 0.020764 0.289636 0.183 Uiso 1 1 calc R U . . .
C2 C 0.6550(3) 0.3725(4) 0.4568(2) 0.0595(14) Uani 1 1 d . . . . .
C3 C 0.6278(2) 0.3878(4) 0.4121(2) 0.0582(14) Uani 1 1 d . . . . .
H4 H 0.628636 0.451907 0.399651 0.070 Uiso 1 1 calc R U . . .
C1 C 0.6863(4) 0.4569(6) 0.4853(3) 0.086(2) Uani 1 1 d . . . . .
C23 C 0.4255(6) -0.0410(5) 0.2853(3) 0.158(5) Uani 1 1 d . U . . .
H18 H 0.417483 0.021437 0.268939 0.238 Uiso 1 1 calc R U . . .
H17 H 0.472127 -0.059487 0.288724 0.238 Uiso 1 1 calc R U . . .
H19 H 0.414682 -0.032866 0.314388 0.238 Uiso 1 1 calc R U . . .
C39 C 0.1800(5) 0.1261(9) 0.3317(3) 0.138(4) Uani 1 1 d . U . . .
H39A H 0.222382 0.094791 0.344634 0.208 Uiso 1 1 calc R U . . .
H39B H 0.147181 0.108835 0.349240 0.208 Uiso 1 1 calc R U . . .
H39C H 0.185642 0.198071 0.331712 0.208 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 1.425(4) . ?
S1 O3 1.433(4) . ?
S1 N1 1.607(4) . ?
S1 C5 1.765(5) . ?
O1 C14 1.234(5) . ?
N3 C22 1.363(6) . ?
N3 C15 1.378(5) . ?
N3 H16 0.8600 . ?
N2 C14 1.353(5) . ?
N2 C9 1.412(5) . ?
N2 H10 0.8600 . ?
N1 C8 1.433(6) . ?
N1 H5 0.8600 . ?
N4 C35 1.517(6) . ?
N4 C26 1.519(6) . ?
N4 C27 1.523(7) . ?
N4 C31 1.531(6) . ?
C17 C18 1.391(6) . ?
C17 C22 1.421(6) . ?
C17 C16 1.429(6) . ?
C15 C16 1.374(6) . ?
C15 C14 1.471(6) . ?
C16 H11 0.9300 . ?
C22 C21 1.399(6) . ?
C9 C8 1.390(6) . ?
C9 C10 1.394(7) . ?
C5 C6 1.373(8) . ?
C5 C4 1.383(7) . ?
C18 C19 1.378(7) . ?
C18 H12 0.9300 . ?
C10 C11 1.391(7) . ?
C10 H6 0.9300 . ?
C21 C20 1.371(7) . ?
C21 H15 0.9300 . ?
C20 C19 1.398(8) . ?
C20 H14 0.9300 . ?
C8 C13 1.383(7) . ?
C27 C28 1.511(7) . ?
C27 H26 0.9700 . ?
C27 H27 0.9700 . ?
C19 H13 0.9300 . ?
C35 C36 1.481(9) . ?
C35 H45 0.9700 . ?
C35 H44 0.9700 . ?
C31 C32 1.508(7) . ?
C31 H36 0.9700 . ?
C31 H35 0.9700 . ?
C13 C12 1.383(8) . ?
C13 H9 0.9300 . ?
C4 C3 1.398(7) . ?
C4 H3 0.9300 . ?
C28 C29 1.531(8) . ?
C28 H28 0.9700 . ?
C28 H29 0.9700 . ?
C26 C25 1.512(7) . ?
C26 H24 0.9700 . ?
C26 H25 0.9700 . ?
C11 C12 1.361(8) . ?
C11 H7 0.9300 . ?
C32 C33 1.526(8) . ?
C32 H38 0.9700 . ?
C32 H37 0.9700 . ?
C6 C7 1.371(8) . ?
C6 H2 0.9300 . ?
F2 C1 1.275(9) . ?
C25 C24 1.453(9) . ?
C25 H22 0.9700 . ?
C25 H23 0.9700 . ?
F1 C1 1.218(8) . ?
C12 H8 0.9300 . ?
C33 C34 1.448(9) . ?
C33 H39 0.9700 . ?
C33 H40 0.9700 . ?
C29 C30 1.492(9) . ?
C29 H30 0.9700 . ?
C29 H31 0.9700 . ?
C7 C2 1.373(9) . ?
C7 H1 0.9300 . ?
F3 C1 1.295(9) . ?
C30 H33 0.9600 . ?
C30 H34 0.9600 . ?
C30 H32 0.9600 . ?
C36 C37 1.541(11) . ?
C36 H46 0.9700 . ?
C36 H47 0.9700 . ?
C34 H43 0.9600 . ?
C34 H42 0.9600 . ?
C34 H41 0.9600 . ?
C24 C23 1.360(11) . ?
C24 H21 0.9700 . ?
C24 H20 0.9700 . ?
C37 C39 1.363(12) . ?
C37 H49 0.9700 . ?
C37 H48 0.9700 . ?
C2 C3 1.371(8) . ?
C2 C1 1.475(8) . ?
C3 H4 0.9300 . ?
C23 H18 0.9600 . ?
C23 H17 0.9600 . ?
C23 H19 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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 O3 119.9(2) . . ?
O2 S1 N1 109.1(2) . . ?
O3 S1 N1 105.6(2) . . ?
O2 S1 C5 106.3(3) . . ?
O3 S1 C5 107.7(2) . . ?
N1 S1 C5 107.7(2) . . ?
C22 N3 C15 108.9(4) . . ?
C22 N3 H16 125.5 . . ?
C15 N3 H16 125.5 . . ?
C14 N2 C9 125.1(4) . . ?
C14 N2 H10 117.5 . . ?
C9 N2 H10 117.5 . . ?
C8 N1 S1 121.7(3) . . ?
C8 N1 H5 119.1 . . ?
S1 N1 H5 119.1 . . ?
C35 N4 C26 110.8(4) . . ?
C35 N4 C27 106.9(3) . . ?
C26 N4 C27 111.4(4) . . ?
C35 N4 C31 111.0(4) . . ?
C26 N4 C31 106.6(3) . . ?
C27 N4 C31 110.2(4) . . ?
C18 C17 C22 119.9(4) . . ?
C18 C17 C16 134.1(4) . . ?
C22 C17 C16 106.0(4) . . ?
C16 C15 N3 109.4(4) . . ?
C16 C15 C14 131.0(4) . . ?
N3 C15 C14 119.3(4) . . ?
C15 C16 C17 107.3(4) . . ?
C15 C16 H11 126.4 . . ?
C17 C16 H11 126.4 . . ?
O1 C14 N2 123.7(4) . . ?
O1 C14 C15 121.3(4) . . ?
N2 C14 C15 115.0(4) . . ?
N3 C22 C21 130.3(4) . . ?
N3 C22 C17 108.3(4) . . ?
C21 C22 C17 121.4(4) . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 N2 118.8(4) . . ?
C10 C9 N2 121.9(4) . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 S1 119.4(4) . . ?
C4 C5 S1 119.9(4) . . ?
C19 C18 C17 118.2(5) . . ?
C19 C18 H12 120.9 . . ?
C17 C18 H12 120.9 . . ?
C11 C10 C9 119.7(5) . . ?
C11 C10 H6 120.1 . . ?
C9 C10 H6 120.1 . . ?
C20 C21 C22 117.1(5) . . ?
C20 C21 H15 121.4 . . ?
C22 C21 H15 121.4 . . ?
C21 C20 C19 122.1(5) . . ?
C21 C20 H14 119.0 . . ?
C19 C20 H14 119.0 . . ?
C13 C8 C9 120.5(4) . . ?
C13 C8 N1 119.1(4) . . ?
C9 C8 N1 120.4(4) . . ?
C28 C27 N4 116.8(4) . . ?
C28 C27 H26 108.1 . . ?
N4 C27 H26 108.1 . . ?
C28 C27 H27 108.1 . . ?
N4 C27 H27 108.1 . . ?
H26 C27 H27 107.3 . . ?
C18 C19 C20 121.3(5) . . ?
C18 C19 H13 119.3 . . ?
C20 C19 H13 119.3 . . ?
C36 C35 N4 116.1(4) . . ?
C36 C35 H45 108.3 . . ?
N4 C35 H45 108.3 . . ?
C36 C35 H44 108.3 . . ?
N4 C35 H44 108.3 . . ?
H45 C35 H44 107.4 . . ?
C32 C31 N4 116.2(4) . . ?
C32 C31 H36 108.2 . . ?
N4 C31 H36 108.2 . . ?
C32 C31 H35 108.2 . . ?
N4 C31 H35 108.2 . . ?
H36 C31 H35 107.4 . . ?
C8 C13 C12 119.3(5) . . ?
C8 C13 H9 120.4 . . ?
C12 C13 H9 120.4 . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 H3 120.6 . . ?
C3 C4 H3 120.6 . . ?
C27 C28 C29 109.3(4) . . ?
C27 C28 H28 109.8 . . ?
C29 C28 H28 109.8 . . ?
C27 C28 H29 109.8 . . ?
C29 C28 H29 109.8 . . ?
H28 C28 H29 108.3 . . ?
C25 C26 N4 114.6(4) . . ?
C25 C26 H24 108.6 . . ?
N4 C26 H24 108.6 . . ?
C25 C26 H25 108.6 . . ?
N4 C26 H25 108.6 . . ?
H24 C26 H25 107.6 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H7 120.0 . . ?
C10 C11 H7 120.0 . . ?
C31 C32 C33 111.6(5) . . ?
C31 C32 H38 109.3 . . ?
C33 C32 H38 109.3 . . ?
C31 C32 H37 109.3 . . ?
C33 C32 H37 109.3 . . ?
H38 C32 H37 108.0 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H2 120.1 . . ?
C5 C6 H2 120.1 . . ?
C24 C25 C26 114.0(6) . . ?
C24 C25 H22 108.8 . . ?
C26 C25 H22 108.8 . . ?
C24 C25 H23 108.8 . . ?
C26 C25 H23 108.8 . . ?
H22 C25 H23 107.7 . . ?
C11 C12 C13 121.2(5) . . ?
C11 C12 H8 119.4 . . ?
C13 C12 H8 119.4 . . ?
C34 C33 C32 114.5(6) . . ?
C34 C33 H39 108.6 . . ?
C32 C33 H39 108.6 . . ?
C34 C33 H40 108.6 . . ?
C32 C33 H40 108.6 . . ?
H39 C33 H40 107.6 . . ?
C30 C29 C28 113.6(5) . . ?
C30 C29 H30 108.8 . . ?
C28 C29 H30 108.8 . . ?
C30 C29 H31 108.8 . . ?
C28 C29 H31 108.8 . . ?
H30 C29 H31 107.7 . . ?
C6 C7 C2 120.4(6) . . ?
C6 C7 H1 119.8 . . ?
C2 C7 H1 119.8 . . ?
C29 C30 H33 109.5 . . ?
C29 C30 H34 109.5 . . ?
H33 C30 H34 109.5 . . ?
C29 C30 H32 109.5 . . ?
H33 C30 H32 109.5 . . ?
H34 C30 H32 109.5 . . ?
C35 C36 C37 110.3(6) . . ?
C35 C36 H46 109.6 . . ?
C37 C36 H46 109.6 . . ?
C35 C36 H47 109.6 . . ?
C37 C36 H47 109.6 . . ?
H46 C36 H47 108.1 . . ?
C33 C34 H43 109.5 . . ?
C33 C34 H42 109.5 . . ?
H43 C34 H42 109.5 . . ?
C33 C34 H41 109.5 . . ?
H43 C34 H41 109.5 . . ?
H42 C34 H41 109.5 . . ?
C23 C24 C25 115.7(8) . . ?
C23 C24 H21 108.4 . . ?
C25 C24 H21 108.4 . . ?
C23 C24 H20 108.4 . . ?
C25 C24 H20 108.4 . . ?
H21 C24 H20 107.4 . . ?
C39 C37 C36 116.9(8) . . ?
C39 C37 H49 108.1 . . ?
C36 C37 H49 108.1 . . ?
C39 C37 H48 108.1 . . ?
C36 C37 H48 108.1 . . ?
H49 C37 H48 107.3 . . ?
C3 C2 C7 120.2(5) . . ?
C3 C2 C1 120.3(6) . . ?
C7 C2 C1 119.5(6) . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H4 120.0 . . ?
C4 C3 H4 120.0 . . ?
F1 C1 F2 106.1(7) . . ?
F1 C1 F3 106.3(9) . . ?
F2 C1 F3 98.1(8) . . ?
F1 C1 C2 116.4(6) . . ?
F2 C1 C2 115.2(7) . . ?
F3 C1 C2 112.7(6) . . ?
C24 C23 H18 109.5 . . ?
C24 C23 H17 109.5 . . ?
H18 C23 H17 109.5 . . ?
C24 C23 H19 109.5 . . ?
H18 C23 H19 109.5 . . ?
H17 C23 H19 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_refine_diff_density_max         0.947
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.078



