# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_40408b
_database_code_depnum_ccdc_archive 'CCDC 1507982'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 F3 N2 O3 S'
_chemical_formula_weight         482.55

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      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                   15.879(3)
_cell_length_b                   9.6304(17)
_cell_length_c                   17.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.401(3)
_cell_angle_gamma                90
_cell_volume                     2519.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3588
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.42

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            15760
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4919
_reflns_number_gt                3219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1526P)²+1.0950P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4919
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2508
_refine_ls_wR_factor_gt          0.2176
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.25146(6) 0.45120(8) 0.06075(5) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.2826(2) 0.5715(3) 0.32245(17) 0.0598(8) Uani 1 1 d . . . . .
N2 N 0.1850(2) 0.7237(3) 0.22985(17) 0.0547(8) Uani 1 1 d . . . . .
O1 O 0.21072(19) 0.4559(3) -0.02594(15) 0.0655(7) Uani 1 1 d . . . . .
O2 O 0.1917(2) 0.4117(3) 0.10124(16) 0.0722(8) Uani 1 1 d . . . . .
O3 O 0.3103(2) 0.5629(3) 0.09901(19) 0.0707(8) Uani 1 1 d . . . . .
F1 F 0.39015(18) 0.3210(3) 0.04633(16) 0.0889(8) Uani 1 1 d . . . . .
F2 F 0.3671(2) 0.2766(3) 0.15592(15) 0.1124(12) Uani 1 1 d . . . . .
F3 F 0.2816(3) 0.1891(2) 0.04323(18) 0.1020(10) Uani 1 1 d . . . . .
C1 C 0.2336(2) 0.6094(4) 0.2481(2) 0.0517(9) Uani 1 1 d . . . . .
C2 C 0.2872(4) 0.6605(6) 0.3899(3) 0.0897(18) Uani 1 1 d . . . . .
C3 C 0.2333(4) 0.7735(6) 0.3729(3) 0.0842(15) Uani 1 1 d . . . . .
H3 H 0.2357 0.8307 0.4167 0.101 Uiso 1 1 calc R U . . .
C4 C 0.1716(4) 0.8146(6) 0.2922(3) 0.104(2) Uani 1 1 d . . . . .
H4A H 0.1829 0.9115 0.2818 0.125 Uiso 1 1 calc R U . . .
H4B H 0.1089 0.8072 0.2893 0.125 Uiso 1 1 calc R U . . .
C5 C 0.3254(3) 0.4359(4) 0.33508(19) 0.0565(9) Uani 1 1 d . . . . .
C6 C 0.2763(2) 0.3221(4) 0.3430(2) 0.0561(9) Uani 1 1 d . . . . .
C7 C 0.3183(3) 0.1926(5) 0.3559(2) 0.0644(10) Uani 1 1 d . . . . .
H7 H 0.2863 0.1140 0.3620 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4062(3) 0.1780(5) 0.3598(2) 0.0704(12) Uani 1 1 d . . . . .
C9 C 0.4522(3) 0.2925(6) 0.3496(2) 0.0810(14) Uani 1 1 d . . . . .
H9 H 0.5117 0.2817 0.3514 0.097 Uiso 1 1 calc R U . . .
C10 C 0.4134(3) 0.4249(6) 0.3366(2) 0.0723(12) Uani 1 1 d . . . . .
C11 C 0.1800(3) 0.3343(5) 0.3380(3) 0.0724(12) Uani 1 1 d . . . . .
H11A H 0.1647 0.2544 0.3637 0.109 Uiso 1 1 calc R U . . .
H11B H 0.1400 0.3383 0.2815 0.109 Uiso 1 1 calc R U . . .
H11C H 0.1732 0.4183 0.3654 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4519(4) 0.0364(7) 0.3751(3) 0.1010(17) Uani 1 1 d . . . . .
H12A H 0.5167 0.0482 0.4024 0.151 Uiso 1 1 calc R U . . .
H12B H 0.4398 -0.0107 0.3238 0.151 Uiso 1 1 calc R U . . .
H12C H 0.4284 -0.0186 0.4089 0.151 Uiso 1 1 calc R U . . .
C13 C 0.4624(4) 0.5513(6) 0.3218(4) 0.107(2) Uani 1 1 d . . . . .
H13A H 0.4528 0.6296 0.3522 0.160 Uiso 1 1 calc R U . . .
H13B H 0.4391 0.5734 0.2644 0.160 Uiso 1 1 calc R U . . .
H13C H 0.5266 0.5316 0.3394 0.160 Uiso 1 1 calc R U . . .
C14 C 0.3424(5) 0.6295(7) 0.4687(3) 0.123(2) Uani 1 1 d . . . . .
H14A H 0.3347 0.6994 0.5051 0.185 Uiso 1 1 calc R U . . .
H14B H 0.4050 0.6283 0.4727 0.185 Uiso 1 1 calc R U . . .
H14C H 0.3262 0.5391 0.4835 0.185 Uiso 1 1 calc R U . . .
C15 C 0.1376(2) 0.7591(4) 0.1454(2) 0.0527(8) Uani 1 1 d . . . . .
C16 C 0.0551(3) 0.6952(4) 0.1035(2) 0.0579(9) Uani 1 1 d . . . . .
C17 C 0.0119(3) 0.7322(4) 0.0228(3) 0.0683(11) Uani 1 1 d . . . . .
H17 H -0.0442 0.6913 -0.0070 0.082 Uiso 1 1 calc R U . . .
C18 C 0.0483(3) 0.8267(5) -0.0156(3) 0.0680(11) Uani 1 1 d . . . . .
C19 C 0.1313(3) 0.8861(5) 0.0294(3) 0.0694(11) Uani 1 1 d . . . . .
H19 H 0.1566 0.9509 0.0041 0.083 Uiso 1 1 calc R U . . .
C20 C 0.1778(3) 0.8538(4) 0.1096(2) 0.0622(10) Uani 1 1 d . . . . .
C21 C 0.0161(3) 0.5869(5) 0.1423(3) 0.0733(12) Uani 1 1 d . . . . .
H21A H 0.0481 0.5000 0.1456 0.110 Uiso 1 1 calc R U . . .
H21B H -0.0474 0.5739 0.1099 0.110 Uiso 1 1 calc R U . . .
H21C H 0.0225 0.6168 0.1965 0.110 Uiso 1 1 calc R U . . .
C22 C -0.0015(4) 0.8637(6) -0.1035(3) 0.0919(15) Uani 1 1 d . . . . .
H22A H -0.0120 0.9631 -0.1084 0.138 Uiso 1 1 calc R U . . .
H22B H -0.0590 0.8153 -0.1236 0.138 Uiso 1 1 calc R U . . .
H22C H 0.0346 0.8365 -0.1350 0.138 Uiso 1 1 calc R U . . .
C23 C 0.2706(3) 0.9125(5) 0.1559(3) 0.0861(14) Uani 1 1 d . . . . .
H23A H 0.3137 0.8371 0.1750 0.129 Uiso 1 1 calc R U . . .
H23B H 0.2690 0.9656 0.2019 0.129 Uiso 1 1 calc R U . . .
H23C H 0.2887 0.9725 0.1205 0.129 Uiso 1 1 calc R U . . .
C24 C 0.3265(3) 0.3021(4) 0.0779(2) 0.0648(10) Uani 1 1 d . . . . .
H1 H 0.233(2) 0.548(3) 0.200(2) 0.049(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.424(3) . ?
S1 O1 1.432(3) . ?
S1 O2 1.433(3) . ?
S1 C24 1.820(4) . ?
N1 C1 1.312(5) . ?
N1 C2 1.449(5) . ?
N1 C5 1.452(5) . ?
N2 C1 1.315(5) . ?
N2 C15 1.448(5) . ?
N2 C4 1.483(5) . ?
F1 C24 1.334(5) . ?
F2 C24 1.316(4) . ?
F3 C24 1.323(5) . ?
C1 H1 1.04(3) . ?
C2 C3 1.349(8) . ?
C2 C14 1.381(8) . ?
C3 C4 1.462(8) . ?
C3 H3 0.9400 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.381(5) . ?
C5 C10 1.392(6) . ?
C6 C7 1.393(6) . ?
C6 C11 1.504(6) . ?
C7 C8 1.380(6) . ?
C7 H7 0.9400 . ?
C8 C9 1.370(7) . ?
C8 C12 1.522(7) . ?
C9 C10 1.398(7) . ?
C9 H9 0.9400 . ?
C10 C13 1.518(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C20 1.390(5) . ?
C15 C16 1.391(5) . ?
C16 C17 1.387(6) . ?
C16 C21 1.500(6) . ?
C17 C18 1.381(6) . ?
C17 H17 0.9400 . ?
C18 C19 1.390(6) . ?
C18 C22 1.509(6) . ?
C19 C20 1.376(5) . ?
C19 H19 0.9400 . ?
C20 C23 1.510(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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 O1 116.55(18) . . ?
O3 S1 O2 113.73(17) . . ?
O1 S1 O2 114.92(17) . . ?
O3 S1 C24 103.91(19) . . ?
O1 S1 C24 102.49(16) . . ?
O2 S1 C24 102.7(2) . . ?
C1 N1 C2 119.6(4) . . ?
C1 N1 C5 118.5(3) . . ?
C2 N1 C5 121.7(4) . . ?
C1 N2 C15 119.2(3) . . ?
C1 N2 C4 122.8(4) . . ?
C15 N2 C4 117.9(4) . . ?
N1 C1 N2 124.0(3) . . ?
N1 C1 H1 119.5(19) . . ?
N2 C1 H1 116.5(19) . . ?
C3 C2 C14 121.1(5) . . ?
C3 C2 N1 117.2(4) . . ?
C14 C2 N1 121.7(6) . . ?
C2 C3 C4 125.5(4) . . ?
C2 C3 H3 117.3 . . ?
C4 C3 H3 117.3 . . ?
C3 C4 N2 109.9(5) . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
N2 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C10 122.5(4) . . ?
C6 C5 N1 118.7(3) . . ?
C10 C5 N1 118.8(4) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C11 122.0(4) . . ?
C7 C6 C11 119.7(3) . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 C12 120.2(5) . . ?
C7 C8 C12 120.6(4) . . ?
C8 C9 C10 122.2(4) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C5 C10 C9 116.9(4) . . ?
C5 C10 C13 120.6(5) . . ?
C9 C10 C13 122.5(4) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 123.2(4) . . ?
C20 C15 N2 118.2(3) . . ?
C16 C15 N2 118.6(3) . . ?
C17 C16 C15 116.8(4) . . ?
C17 C16 C21 121.2(4) . . ?
C15 C16 C21 122.0(4) . . ?
C18 C17 C16 122.5(4) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C19 118.0(4) . . ?
C17 C18 C22 120.5(4) . . ?
C19 C18 C22 121.6(4) . . ?
C20 C19 C18 122.5(4) . . ?
C20 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
C19 C20 C15 117.1(4) . . ?
C19 C20 C23 121.7(4) . . ?
C15 C20 C23 121.2(4) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F2 C24 F3 108.0(3) . . ?
F2 C24 F1 108.0(4) . . ?
F3 C24 F1 106.3(3) . . ?
F2 C24 S1 111.3(3) . . ?
F3 C24 S1 111.2(3) . . ?
F1 C24 S1 111.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -1.9(5) . . . . ?
C5 N1 C1 N2 173.5(3) . . . . ?
C15 N2 C1 N1 176.4(3) . . . . ?
C4 N2 C1 N1 -7.5(5) . . . . ?
C1 N1 C2 C3 5.9(6) . . . . ?
C5 N1 C2 C3 -169.3(4) . . . . ?
C1 N1 C2 C14 -175.8(5) . . . . ?
C5 N1 C2 C14 9.0(6) . . . . ?
C14 C2 C3 C4 -179.1(5) . . . . ?
N1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 N2 -7.1(7) . . . . ?
C1 N2 C4 C3 11.3(5) . . . . ?
C15 N2 C4 C3 -172.6(3) . . . . ?
C1 N1 C5 C6 -85.7(4) . . . . ?
C2 N1 C5 C6 89.5(4) . . . . ?
C1 N1 C5 C10 92.6(4) . . . . ?
C2 N1 C5 C10 -92.1(4) . . . . ?
C10 C5 C6 C7 2.4(5) . . . . ?
N1 C5 C6 C7 -179.4(3) . . . . ?
C10 C5 C6 C11 -177.5(3) . . . . ?
N1 C5 C6 C11 0.7(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C11 C6 C7 C8 179.2(3) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C6 C7 C8 C12 179.1(4) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C12 C8 C9 C10 -179.0(4) . . . . ?
C6 C5 C10 C9 -2.3(5) . . . . ?
N1 C5 C10 C9 179.5(3) . . . . ?
C6 C5 C10 C13 175.7(4) . . . . ?
N1 C5 C10 C13 -2.5(5) . . . . ?
C8 C9 C10 C5 0.5(6) . . . . ?
C8 C9 C10 C13 -177.4(4) . . . . ?
C1 N2 C15 C20 -97.8(4) . . . . ?
C4 N2 C15 C20 85.9(4) . . . . ?
C1 N2 C15 C16 81.1(4) . . . . ?
C4 N2 C15 C16 -95.2(4) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?
N2 C15 C16 C17 179.9(3) . . . . ?
C20 C15 C16 C21 176.1(4) . . . . ?
N2 C15 C16 C21 -2.7(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C21 C16 C17 C18 -176.9(4) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C16 C17 C18 C22 -179.8(4) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C22 C18 C19 C20 -179.9(4) . . . . ?
C18 C19 C20 C15 -0.9(6) . . . . ?
C18 C19 C20 C23 176.0(4) . . . . ?
C16 C15 C20 C19 1.4(6) . . . . ?
N2 C15 C20 C19 -179.7(3) . . . . ?
C16 C15 C20 C23 -175.5(4) . . . . ?
N2 C15 C20 C23 3.3(6) . . . . ?
O3 S1 C24 F2 61.6(4) . . . . ?
O1 S1 C24 F2 -176.6(3) . . . . ?
O2 S1 C24 F2 -57.1(4) . . . . ?
O3 S1 C24 F3 -178.0(3) . . . . ?
O1 S1 C24 F3 -56.2(3) . . . . ?
O2 S1 C24 F3 63.3(3) . . . . ?
O3 S1 C24 F1 -59.3(3) . . . . ?
O1 S1 C24 F1 62.5(3) . . . . ?
O2 S1 C24 F1 -178.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 1.04(3) 2.09(4) 3.093(4) 163(3) .
C3 H3 O1 0.94 2.39 3.254(5) 153.1 4_576

_refine_diff_density_max         1.596
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_a40411ba
_database_code_depnum_ccdc_archive 'CCDC 1507983'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H41 Cl2 F3 N2 O3 S'
_chemical_formula_weight         637.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   20.338(7)
_cell_length_b                   16.179(5)
_cell_length_c                   21.087(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6938(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3490
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            25983
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6084
_reflns_number_gt                2514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1259P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6084
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1718
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2294
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_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 0.15970(6) 0.14021(8) 0.14860(6) 0.0747(4) Uani 1 1 d . . . . .
N1 N 0.32639(15) 0.94122(18) 0.07689(13) 0.0486(8) Uani 1 1 d . . . . .
N2 N 0.22915(14) 0.88321(19) 0.07085(12) 0.0481(8) Uani 1 1 d . . . . .
O1 O 0.16738(14) 0.22113(18) 0.17470(14) 0.0814(9) Uani 1 1 d . . . . .
O2 O 0.1881(2) 0.0740(2) 0.1833(2) 0.1244(13) Uani 1 1 d . . . . .
O3 O 0.1735(2) 0.1340(2) 0.08291(16) 0.1285(15) Uani 1 1 d . . . . .
F1 F 0.05449(19) 0.0495(3) 0.1319(2) 0.1685(16) Uani 1 1 d . . . . .
F2 F 0.05170(19) 0.1280(3) 0.2119(2) 0.1831(19) Uani 1 1 d . . . . .
F3 F 0.04013(19) 0.1776(3) 0.1210(2) 0.1718(17) Uani 1 1 d . . . . .
C1 C 0.26248(19) 0.9475(3) 0.08867(16) 0.0459(9) Uani 1 1 d . . . . .
H1 H 0.2409(14) 0.994(2) 0.1120(13) 0.039(9) Uiso 1 1 d . . . . .
C2 C 0.33938(19) 0.8628(2) 0.04752(16) 0.0497(10) Uani 1 1 d . . . . .
C3 C 0.27440(18) 0.8212(2) 0.04275(17) 0.0562(10) Uani 1 1 d . . . . .
H3A H 0.2631 0.8098 -0.0011 0.067 Uiso 1 1 calc R U . . .
H3B H 0.2738 0.7700 0.0666 0.067 Uiso 1 1 calc R U . . .
C4 C 0.37651(18) 1.0004(2) 0.09374(18) 0.0532(10) Uani 1 1 d . . . . .
C5 C 0.4063(2) 0.9935(3) 0.15251(19) 0.0630(11) Uani 1 1 d . . . . .
C6 C 0.4550(2) 1.0505(3) 0.1674(2) 0.0877(15) Uani 1 1 d . . . . .
H6 H 0.4758 1.0476 0.2066 0.105 Uiso 1 1 calc R U . . .
C7 C 0.4733(3) 1.1118(3) 0.1248(3) 0.0950(16) Uani 1 1 d . . . . .
H7 H 0.5058 1.1497 0.1356 0.114 Uiso 1 1 calc R U . . .
C8 C 0.4438(2) 1.1161(3) 0.0673(3) 0.0843(14) Uani 1 1 d . . . . .
H8 H 0.4564 1.1576 0.0393 0.101 Uiso 1 1 calc R U . . .
C9 C 0.3949(2) 1.0603(3) 0.0485(2) 0.0651(11) Uani 1 1 d . . . . .
C10 C 0.3860(2) 0.9286(3) 0.2005(2) 0.0797(14) Uani 1 1 d . . . . .
H10 H 0.3586 0.8881 0.1783 0.096 Uiso 1 1 calc R U . . .
C11 C 0.4450(3) 0.8822(4) 0.2282(3) 0.134(2) Uani 1 1 d . . . . .
H11A H 0.4688 0.8556 0.1946 0.201 Uiso 1 1 calc R U . . .
H11B H 0.4298 0.8414 0.2578 0.201 Uiso 1 1 calc R U . . .
H11C H 0.4734 0.9206 0.2496 0.201 Uiso 1 1 calc R U . . .
C12 C 0.3441(3) 0.9673(4) 0.2520(2) 0.134(2) Uani 1 1 d . . . . .
H12A H 0.3702 1.0053 0.2762 0.201 Uiso 1 1 calc R U . . .
H12B H 0.3275 0.9248 0.2795 0.201 Uiso 1 1 calc R U . . .
H12C H 0.3079 0.9963 0.2330 0.201 Uiso 1 1 calc R U . . .
C13 C 0.3630(2) 1.0655(3) -0.01570(19) 0.0728(13) Uani 1 1 d . . . . .
H13 H 0.3404 1.0129 -0.0234 0.087 Uiso 1 1 calc R U . . .
C14 C 0.3117(3) 1.1334(4) -0.0173(3) 0.125(2) Uani 1 1 d . . . . .
H14A H 0.2764 1.1197 0.0111 0.188 Uiso 1 1 calc R U . . .
H14B H 0.2948 1.1388 -0.0596 0.188 Uiso 1 1 calc R U . . .
H14C H 0.3313 1.1847 -0.0044 0.188 Uiso 1 1 calc R U . . .
C15 C 0.4132(3) 1.0784(4) -0.0700(2) 0.120(2) Uani 1 1 d . . . . .
H15A H 0.4359 1.1298 -0.0639 0.180 Uiso 1 1 calc R U . . .
H15B H 0.3905 1.0795 -0.1099 0.180 Uiso 1 1 calc R U . . .
H15C H 0.4444 1.0339 -0.0700 0.180 Uiso 1 1 calc R U . . .
C16 C 0.3979(2) 0.8381(3) 0.03023(19) 0.0753(13) Uani 1 1 d . . . . .
H16A H 0.4342 0.8720 0.0368 0.090 Uiso 1 1 calc R U . . .
H16B H 0.4033 0.7865 0.0114 0.090 Uiso 1 1 calc R U . . .
C17 C 0.15870(18) 0.8711(2) 0.07610(17) 0.0497(10) Uani 1 1 d . . . . .
C18 C 0.1197(2) 0.8908(2) 0.02316(18) 0.0627(11) Uani 1 1 d . . . . .
C19 C 0.0528(2) 0.8782(3) 0.0287(2) 0.0787(14) Uani 1 1 d . . . . .
H19 H 0.0253 0.8897 -0.0055 0.094 Uiso 1 1 calc R U . . .
C20 C 0.0261(2) 0.8486(3) 0.0849(3) 0.0841(14) Uani 1 1 d . . . . .
H20 H -0.0191 0.8416 0.0883 0.101 Uiso 1 1 calc R U . . .
C21 C 0.0655(2) 0.8298(3) 0.1351(2) 0.0718(12) Uani 1 1 d . . . . .
H21 H 0.0464 0.8098 0.1721 0.086 Uiso 1 1 calc R U . . .
C22 C 0.13338(19) 0.8396(2) 0.13242(18) 0.0574(11) Uani 1 1 d . . . . .
C23 C 0.1481(2) 0.9241(3) -0.03753(19) 0.0768(13) Uani 1 1 d . . . . .
H23 H 0.1960 0.9266 -0.0327 0.092 Uiso 1 1 calc R U . . .
C24 C 0.1327(3) 0.8674(4) -0.0944(2) 0.122(2) Uani 1 1 d . . . . .
H24A H 0.1440 0.8114 -0.0840 0.183 Uiso 1 1 calc R U . . .
H24B H 0.1577 0.8850 -0.1306 0.183 Uiso 1 1 calc R U . . .
H24C H 0.0866 0.8705 -0.1041 0.183 Uiso 1 1 calc R U . . .
C25 C 0.1235(3) 1.0109(3) -0.0514(3) 0.1200(19) Uani 1 1 d . . . . .
H25A H 0.0765 1.0100 -0.0561 0.180 Uiso 1 1 calc R U . . .
H25B H 0.1431 1.0306 -0.0900 0.180 Uiso 1 1 calc R U . . .
H25C H 0.1352 1.0469 -0.0171 0.180 Uiso 1 1 calc R U . . .
C26 C 0.1754(2) 0.8160(3) 0.18903(19) 0.0733(13) Uani 1 1 d . . . . .
H26 H 0.2215 0.8233 0.1768 0.088 Uiso 1 1 calc R U . . .
C27 C 0.1658(2) 0.7245(3) 0.2066(2) 0.1064(18) Uani 1 1 d . . . . .
H27A H 0.1210 0.7156 0.2195 0.160 Uiso 1 1 calc R U . . .
H27B H 0.1947 0.7103 0.2409 0.160 Uiso 1 1 calc R U . . .
H27C H 0.1755 0.6905 0.1705 0.160 Uiso 1 1 calc R U . . .
C28 C 0.1625(3) 0.8714(4) 0.2466(2) 0.116(2) Uani 1 1 d . . . . .
H28A H 0.1730 0.9276 0.2361 0.175 Uiso 1 1 calc R U . . .
H28B H 0.1894 0.8536 0.2814 0.175 Uiso 1 1 calc R U . . .
H28C H 0.1170 0.8676 0.2584 0.175 Uiso 1 1 calc R U . . .
C29 C 0.0732(3) 0.1226(4) 0.1542(3) 0.1001(17) Uani 1 1 d . . . . .
C30 C 0.1753(4) 0.1793(6) 0.3279(3) 0.192(4) Uani 1 1 d . . . . .
H30A H 0.1342 0.1767 0.3047 0.230 Uiso 1 1 calc R U . . .
H30B H 0.2100 0.1879 0.2970 0.230 Uiso 1 1 calc R U . . .
Cl1 Cl 0.17271(14) 0.26289(17) 0.37537(10) 0.2055(12) Uani 1 1 d . . . . .
Cl2 Cl 0.18758(18) 0.08831(18) 0.36196(10) 0.2413(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.417(3) . ?
S1 O2 1.421(4) . ?
S1 O1 1.429(3) . ?
S1 C29 1.786(6) . ?
N1 C1 1.327(4) . ?
N1 C2 1.437(5) . ?
N1 C4 1.443(5) . ?
N2 C1 1.297(4) . ?
N2 C17 1.451(4) . ?
N2 C3 1.484(4) . ?
F1 C29 1.330(6) . ?
F2 C29 1.296(6) . ?
F3 C29 1.317(6) . ?
C1 H1 1.00(3) . ?
C2 C16 1.308(5) . ?
C2 C3 1.486(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.384(5) . ?
C4 C9 1.411(5) . ?
C5 C6 1.390(6) . ?
C5 C10 1.515(6) . ?
C6 C7 1.389(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(6) . ?
C8 H8 0.9300 . ?
C9 C13 1.504(6) . ?
C10 C12 1.516(7) . ?
C10 C11 1.532(7) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.515(6) . ?
C13 C15 1.549(6) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 C22 1.391(5) . ?
C17 C18 1.406(5) . ?
C18 C19 1.381(6) . ?
C18 C23 1.504(6) . ?
C19 C20 1.387(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(5) . ?
C21 H21 0.9300 . ?
C22 C26 1.517(5) . ?
C23 C25 1.520(7) . ?
C23 C24 1.542(6) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C28 1.531(6) . ?
C26 C27 1.539(6) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 Cl2 1.657(9) . ?
C30 Cl1 1.683(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

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 O2 111.7(3) . . ?
O3 S1 O1 114.8(2) . . ?
O2 S1 O1 116.6(2) . . ?
O3 S1 C29 104.4(3) . . ?
O2 S1 C29 104.3(3) . . ?
O1 S1 C29 103.2(2) . . ?
C1 N1 C2 109.2(3) . . ?
C1 N1 C4 126.5(3) . . ?
C2 N1 C4 124.2(3) . . ?
C1 N2 C17 127.1(3) . . ?
C1 N2 C3 109.5(3) . . ?
C17 N2 C3 123.5(3) . . ?
N2 C1 N1 113.3(4) . . ?
N2 C1 H1 120.9(17) . . ?
N1 C1 H1 125.6(17) . . ?
C16 C2 N1 123.9(4) . . ?
C16 C2 C3 130.7(4) . . ?
N1 C2 C3 105.4(3) . . ?
N2 C3 C2 102.6(3) . . ?
N2 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C9 123.0(4) . . ?
C5 C4 N1 118.4(3) . . ?
C9 C4 N1 118.5(3) . . ?
C4 C5 C6 117.4(4) . . ?
C4 C5 C10 122.3(4) . . ?
C6 C5 C10 120.2(4) . . ?
C7 C6 C5 121.3(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 122.3(5) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C4 116.2(4) . . ?
C8 C9 C13 121.6(4) . . ?
C4 C9 C13 122.2(4) . . ?
C5 C10 C12 110.3(4) . . ?
C5 C10 C11 112.3(4) . . ?
C12 C10 C11 111.7(4) . . ?
C5 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 110.9(4) . . ?
C9 C13 C15 112.9(4) . . ?
C14 C13 C15 109.9(4) . . ?
C9 C13 H13 107.6 . . ?
C14 C13 H13 107.6 . . ?
C15 C13 H13 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16A 120.0 . . ?
C2 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C22 C17 C18 123.5(4) . . ?
C22 C17 N2 118.7(3) . . ?
C18 C17 N2 117.8(3) . . ?
C19 C18 C17 117.1(4) . . ?
C19 C18 C23 120.2(4) . . ?
C17 C18 C23 122.7(4) . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C17 C22 C21 116.3(4) . . ?
C17 C22 C26 123.8(3) . . ?
C21 C22 C26 119.9(4) . . ?
C18 C23 C25 111.6(4) . . ?
C18 C23 C24 111.8(4) . . ?
C25 C23 C24 109.4(4) . . ?
C18 C23 H23 108.0 . . ?
C25 C23 H23 108.0 . . ?
C24 C23 H23 108.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C28 112.4(4) . . ?
C22 C26 C27 111.1(4) . . ?
C28 C26 C27 110.5(4) . . ?
C22 C26 H26 107.6 . . ?
C28 C26 H26 107.6 . . ?
C27 C26 H26 107.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
F2 C29 F3 106.4(6) . . ?
F2 C29 F1 107.2(5) . . ?
F3 C29 F1 105.5(5) . . ?
F2 C29 S1 112.6(4) . . ?
F3 C29 S1 111.1(4) . . ?
F1 C29 S1 113.6(5) . . ?
Cl2 C30 Cl1 117.4(4) . . ?
Cl2 C30 H30A 107.9 . . ?
Cl1 C30 H30A 107.9 . . ?
Cl2 C30 H30B 107.9 . . ?
Cl1 C30 H30B 107.9 . . ?
H30A C30 H30B 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N2 C1 N1 -179.1(3) . . . . ?
C3 N2 C1 N1 0.5(4) . . . . ?
C2 N1 C1 N2 -0.3(4) . . . . ?
C4 N1 C1 N2 -176.9(3) . . . . ?
C1 N1 C2 C16 -179.9(4) . . . . ?
C4 N1 C2 C16 -3.2(5) . . . . ?
C1 N1 C2 C3 0.0(4) . . . . ?
C4 N1 C2 C3 176.6(3) . . . . ?
C1 N2 C3 C2 -0.4(3) . . . . ?
C17 N2 C3 C2 179.2(3) . . . . ?
C16 C2 C3 N2 -179.9(4) . . . . ?
N1 C2 C3 N2 0.3(3) . . . . ?
C1 N1 C4 C5 88.7(4) . . . . ?
C2 N1 C4 C5 -87.3(4) . . . . ?
C1 N1 C4 C9 -94.0(4) . . . . ?
C2 N1 C4 C9 89.9(4) . . . . ?
C9 C4 C5 C6 2.1(6) . . . . ?
N1 C4 C5 C6 179.2(4) . . . . ?
C9 C4 C5 C10 -179.9(4) . . . . ?
N1 C4 C5 C10 -2.8(6) . . . . ?
C4 C5 C6 C7 -0.3(7) . . . . ?
C10 C5 C6 C7 -178.4(4) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C6 C7 C8 C9 -0.3(7) . . . . ?
C7 C8 C9 C4 1.8(6) . . . . ?
C7 C8 C9 C13 -179.4(4) . . . . ?
C5 C4 C9 C8 -2.8(6) . . . . ?
N1 C4 C9 C8 -179.9(3) . . . . ?
C5 C4 C9 C13 178.5(4) . . . . ?
N1 C4 C9 C13 1.4(5) . . . . ?
C4 C5 C10 C12 -102.9(5) . . . . ?
C6 C5 C10 C12 75.0(5) . . . . ?
C4 C5 C10 C11 131.8(4) . . . . ?
C6 C5 C10 C11 -50.3(6) . . . . ?
C8 C9 C13 C14 -78.4(5) . . . . ?
C4 C9 C13 C14 100.2(5) . . . . ?
C8 C9 C13 C15 45.4(6) . . . . ?
C4 C9 C13 C15 -135.9(4) . . . . ?
C1 N2 C17 C22 -85.9(4) . . . . ?
C3 N2 C17 C22 94.6(4) . . . . ?
C1 N2 C17 C18 95.0(4) . . . . ?
C3 N2 C17 C18 -84.5(4) . . . . ?
C22 C17 C18 C19 0.5(6) . . . . ?
N2 C17 C18 C19 179.5(4) . . . . ?
C22 C17 C18 C23 -179.4(4) . . . . ?
N2 C17 C18 C23 -0.4(6) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C23 C18 C19 C20 -179.1(4) . . . . ?
C18 C19 C20 C21 -1.4(7) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C18 C17 C22 C21 -1.5(6) . . . . ?
N2 C17 C22 C21 179.5(3) . . . . ?
C18 C17 C22 C26 178.3(4) . . . . ?
N2 C17 C22 C26 -0.7(6) . . . . ?
C20 C21 C22 C17 1.1(6) . . . . ?
C20 C21 C22 C26 -178.7(4) . . . . ?
C19 C18 C23 C25 63.5(6) . . . . ?
C17 C18 C23 C25 -116.6(5) . . . . ?
C19 C18 C23 C24 -59.3(5) . . . . ?
C17 C18 C23 C24 120.6(4) . . . . ?
C17 C22 C26 C28 114.2(5) . . . . ?
C21 C22 C26 C28 -66.1(5) . . . . ?
C17 C22 C26 C27 -121.5(4) . . . . ?
C21 C22 C26 C27 58.3(5) . . . . ?
O3 S1 C29 F2 -178.6(5) . . . . ?
O2 S1 C29 F2 64.1(5) . . . . ?
O1 S1 C29 F2 -58.2(5) . . . . ?
O3 S1 C29 F3 -59.3(5) . . . . ?
O2 S1 C29 F3 -176.6(4) . . . . ?
O1 S1 C29 F3 61.0(5) . . . . ?
O3 S1 C29 F1 59.4(5) . . . . ?
O2 S1 C29 F1 -57.9(5) . . . . ?
O1 S1 C29 F1 179.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 1.00(3) 2.26(3) 3.233(6) 166(2) 1_565

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

