# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd17086
_database_code_depnum_ccdc_archive 'CCDC 1534541'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 F I2 N O2 S'
_chemical_formula_weight         673.29

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7048(10)
_cell_length_b                   10.5461(13)
_cell_length_c                   13.9946(17)
_cell_angle_alpha                82.330(2)
_cell_angle_beta                 79.359(2)
_cell_angle_gamma                79.100(2)
_cell_volume                     1233.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3915
_cell_measurement_theta_min      5.187
_cell_measurement_theta_max      55.712

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.664
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4916
_exptl_absorpt_correction_T_max  0.7456
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7115
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.488
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4586
_reflns_number_gt                4011
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0426P)²+0.1145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0074(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_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
I1 I 1.29221(2) 0.10588(2) 1.02685(2) 0.04969(10) Uani 1 1 d . . . . .
I2 I 0.70022(3) 0.44115(3) 1.06849(2) 0.06044(11) Uani 1 1 d . . . . .
N1 N 1.1751(3) 0.1552(2) 0.81948(18) 0.0393(6) Uani 1 1 d . . . . .
O1 O 1.1259(3) -0.0709(2) 0.84027(18) 0.0596(7) Uani 1 1 d . . . . .
O2 O 1.3420(3) -0.0039(3) 0.7124(2) 0.0670(7) Uani 1 1 d . . . . .
S1 S 1.18529(10) 0.02241(8) 0.76534(6) 0.0461(2) Uani 1 1 d . . . . .
F1 F 0.5979(3) 0.7940(2) 0.58820(19) 0.0819(7) Uani 1 1 d . . . . .
C1 C 1.2439(4) 0.2615(3) 0.7663(2) 0.0396(7) Uani 1 1 d . . . . .
C2 C 1.4063(4) 0.2504(4) 0.7379(3) 0.0517(8) Uani 1 1 d . . . . .
H2 H 1.4723 0.1727 0.7525 0.062 Uiso 1 1 calc R U . . .
C3 C 1.4694(4) 0.3546(4) 0.6882(3) 0.0587(10) Uani 1 1 d . . . . .
H3 H 1.5783 0.3473 0.6680 0.070 Uiso 1 1 calc R U . . .
C4 C 1.3714(4) 0.4701(4) 0.6681(3) 0.0609(10) Uani 1 1 d . . . . .
H4 H 1.4149 0.5403 0.6339 0.073 Uiso 1 1 calc R U . . .
C5 C 1.2098(4) 0.4829(4) 0.6980(2) 0.0492(8) Uani 1 1 d . . . . .
H5 H 1.1451 0.5617 0.6843 0.059 Uiso 1 1 calc R U . . .
C6 C 1.1431(4) 0.3780(3) 0.7486(2) 0.0407(7) Uani 1 1 d . . . . .
C7 C 0.9709(3) 0.3871(3) 0.7828(2) 0.0374(7) Uani 1 1 d . . . . .
C8 C 0.9174(3) 0.2988(3) 0.8528(2) 0.0343(6) Uani 1 1 d . . . . .
C9 C 1.0385(3) 0.1919(3) 0.8944(2) 0.0357(6) Uani 1 1 d . . . . .
H9 H 0.9881 0.1157 0.9188 0.043 Uiso 1 1 calc R U . . .
C10 C 1.0946(3) 0.2378(3) 0.9795(2) 0.0384(7) Uani 1 1 d . . . . .
H10A H 1.0076 0.2468 1.0339 0.046 Uiso 1 1 calc R U . . .
H10B H 1.1248 0.3225 0.9594 0.046 Uiso 1 1 calc R U . . .
C11 C 0.7436(3) 0.2929(3) 0.8864(2) 0.0388(7) Uani 1 1 d . . . . .
H11A H 0.7192 0.2205 0.8592 0.047 Uiso 1 1 calc R U . . .
H11B H 0.6827 0.3714 0.8587 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6865(4) 0.2784(3) 0.9954(2) 0.0417(7) Uani 1 1 d . . . . .
H12A H 0.7490 0.2016 1.0241 0.050 Uiso 1 1 calc R U . . .
H12B H 0.5772 0.2648 1.0071 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8668(4) 0.4947(3) 0.7334(2) 0.0403(7) Uani 1 1 d . . . . .
C14 C 0.8552(4) 0.4918(3) 0.6357(2) 0.0462(8) Uani 1 1 d . . . . .
H14 H 0.9103 0.4217 0.6027 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7628(4) 0.5919(4) 0.5875(3) 0.0519(8) Uani 1 1 d . . . . .
H15 H 0.7542 0.5893 0.5226 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6845(4) 0.6944(4) 0.6365(3) 0.0531(9) Uani 1 1 d . . . . .
C17 C 0.6908(5) 0.6989(4) 0.7326(3) 0.0595(10) Uani 1 1 d . . . . .
H17 H 0.6337 0.7685 0.7655 0.071 Uiso 1 1 calc R U . . .
C18 C 0.7826(5) 0.5993(4) 0.7799(3) 0.0570(10) Uani 1 1 d . . . . .
H18 H 0.7882 0.6025 0.8452 0.068 Uiso 1 1 calc R U . . .
C19 C 1.0531(4) 0.0628(3) 0.6817(2) 0.0428(7) Uani 1 1 d . . . . .
C20 C 0.9071(4) 0.0250(4) 0.7042(3) 0.0521(8) Uani 1 1 d . . . . .
H20 H 0.8795 -0.0240 0.7632 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8014(5) 0.0598(4) 0.6393(3) 0.0620(10) Uani 1 1 d . . . . .
H21 H 0.7036 0.0321 0.6541 0.074 Uiso 1 1 calc R U . . .
C22 C 0.8386(5) 0.1354(4) 0.5523(3) 0.0599(10) Uani 1 1 d . . . . .
C23 C 0.9849(5) 0.1707(4) 0.5309(3) 0.0604(10) Uani 1 1 d . . . . .
H23 H 1.0121 0.2200 0.4720 0.072 Uiso 1 1 calc R U . . .
C24 C 1.0930(5) 0.1358(3) 0.5937(3) 0.0529(9) Uani 1 1 d . . . . .
H24 H 1.1922 0.1609 0.5774 0.064 Uiso 1 1 calc R U . . .
C25 C 0.7200(6) 0.1761(5) 0.4831(4) 0.0939(17) Uani 1 1 d . . . . .
H25A H 0.6455 0.2503 0.5046 0.141 Uiso 1 1 calc R U . . .
H25B H 0.6645 0.1059 0.4821 0.141 Uiso 1 1 calc R U . . .
H25C H 0.7745 0.1980 0.4186 0.141 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
I1 C10 2.146(3) . ?
I2 C12 2.144(3) . ?
N1 C1 1.427(4) . ?
N1 C9 1.462(4) . ?
N1 S1 1.659(3) . ?
O1 S1 1.433(3) . ?
O2 S1 1.423(3) . ?
S1 C19 1.748(3) . ?
F1 C16 1.352(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(4) . ?
C7 C8 1.340(4) . ?
C7 C13 1.490(4) . ?
C8 C11 1.510(4) . ?
C8 C9 1.524(4) . ?
C9 C10 1.533(4) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.511(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.374(5) . ?
C13 C14 1.395(4) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(5) . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.372(5) . ?
C19 C24 1.385(5) . ?
C20 C21 1.378(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(6) . ?
C22 C25 1.509(5) . ?
C23 C24 1.373(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C1 N1 C9 114.6(2) . . ?
C1 N1 S1 119.4(2) . . ?
C9 N1 S1 118.9(2) . . ?
O2 S1 O1 120.75(17) . . ?
O2 S1 N1 106.47(15) . . ?
O1 S1 N1 105.90(14) . . ?
O2 S1 C19 108.40(16) . . ?
O1 S1 C19 108.07(17) . . ?
N1 S1 C19 106.40(14) . . ?
C2 C1 C6 121.3(3) . . ?
C2 C1 N1 120.9(3) . . ?
C6 C1 N1 117.7(3) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 119.7(3) . . ?
C5 C6 C7 122.2(3) . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 C13 124.2(3) . . ?
C6 C7 C13 116.3(3) . . ?
C7 C8 C11 123.5(3) . . ?
C7 C8 C9 118.1(3) . . ?
C11 C8 C9 118.2(2) . . ?
N1 C9 C8 111.1(2) . . ?
N1 C9 C10 109.4(2) . . ?
C8 C9 C10 110.0(2) . . ?
N1 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C9 C10 I1 112.24(19) . . ?
C9 C10 H10A 109.2 . . ?
I1 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
I1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C8 C11 C12 117.0(2) . . ?
C8 C11 H11A 108.0 . . ?
C12 C11 H11A 108.0 . . ?
C8 C11 H11B 108.0 . . ?
C12 C11 H11B 108.0 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 I2 114.5(2) . . ?
C11 C12 H12A 108.6 . . ?
I2 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
I2 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C18 C13 C14 117.9(3) . . ?
C18 C13 C7 122.6(3) . . ?
C14 C13 C7 119.5(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
F1 C16 C15 118.7(3) . . ?
F1 C16 C17 119.4(3) . . ?
C15 C16 C17 121.8(3) . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C13 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C20 C19 C24 119.7(3) . . ?
C20 C19 S1 119.9(3) . . ?
C24 C19 S1 120.4(3) . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.9(4) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 118.3(3) . . ?
C23 C22 C25 121.3(4) . . ?
C21 C22 C25 120.4(4) . . ?
C22 C23 C24 121.9(4) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C19 119.3(4) . . ?
C23 C24 H24 120.3 . . ?
C19 C24 H24 120.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 S1 O2 42.8(3) . . . . ?
C9 N1 S1 O2 -168.2(2) . . . . ?
C1 N1 S1 O1 172.5(2) . . . . ?
C9 N1 S1 O1 -38.5(2) . . . . ?
C1 N1 S1 C19 -72.7(3) . . . . ?
C9 N1 S1 C19 76.3(2) . . . . ?
C9 N1 C1 C2 142.8(3) . . . . ?
S1 N1 C1 C2 -66.9(4) . . . . ?
C9 N1 C1 C6 -33.9(4) . . . . ?
S1 N1 C1 C6 116.4(3) . . . . ?
C6 C1 C2 C3 -2.4(5) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C2 C1 C6 C5 2.3(5) . . . . ?
N1 C1 C6 C5 179.0(3) . . . . ?
C2 C1 C6 C7 -178.1(3) . . . . ?
N1 C1 C6 C7 -1.4(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C1 C6 C7 C8 18.9(4) . . . . ?
C5 C6 C7 C8 -161.6(3) . . . . ?
C1 C6 C7 C13 -159.4(3) . . . . ?
C5 C6 C7 C13 20.2(4) . . . . ?
C6 C7 C8 C11 -174.5(3) . . . . ?
C13 C7 C8 C11 3.6(5) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C13 C7 C8 C9 178.2(3) . . . . ?
C1 N1 C9 C8 50.4(3) . . . . ?
S1 N1 C9 C8 -100.0(3) . . . . ?
C1 N1 C9 C10 -71.2(3) . . . . ?
S1 N1 C9 C10 138.4(2) . . . . ?
C7 C8 C9 N1 -33.7(4) . . . . ?
C11 C8 C9 N1 141.3(3) . . . . ?
C7 C8 C9 C10 87.6(3) . . . . ?
C11 C8 C9 C10 -97.5(3) . . . . ?
N1 C9 C10 I1 -48.4(3) . . . . ?
C8 C9 C10 I1 -170.63(19) . . . . ?
C7 C8 C11 C12 -133.2(3) . . . . ?
C9 C8 C11 C12 52.2(4) . . . . ?
C8 C11 C12 I2 65.6(3) . . . . ?
C8 C7 C13 C18 71.2(5) . . . . ?
C6 C7 C13 C18 -110.6(4) . . . . ?
C8 C7 C13 C14 -110.0(4) . . . . ?
C6 C7 C13 C14 68.1(4) . . . . ?
C18 C13 C14 C15 0.5(5) . . . . ?
C7 C13 C14 C15 -178.3(3) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 F1 178.1(3) . . . . ?
C14 C15 C16 C17 -2.1(6) . . . . ?
F1 C16 C17 C18 -178.1(4) . . . . ?
C15 C16 C17 C18 2.1(6) . . . . ?
C16 C17 C18 C13 -0.7(6) . . . . ?
C14 C13 C18 C17 -0.5(6) . . . . ?
C7 C13 C18 C17 178.2(4) . . . . ?
O2 S1 C19 C20 144.3(3) . . . . ?
O1 S1 C19 C20 11.8(3) . . . . ?
N1 S1 C19 C20 -101.6(3) . . . . ?
O2 S1 C19 C24 -37.5(3) . . . . ?
O1 S1 C19 C24 -170.0(3) . . . . ?
N1 S1 C19 C24 76.6(3) . . . . ?
C24 C19 C20 C21 0.1(5) . . . . ?
S1 C19 C20 C21 178.3(3) . . . . ?
C19 C20 C21 C22 -1.6(6) . . . . ?
C20 C21 C22 C23 2.3(6) . . . . ?
C20 C21 C22 C25 -178.2(3) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C25 C22 C23 C24 179.1(3) . . . . ?
C22 C23 C24 C19 -0.2(5) . . . . ?
C20 C19 C24 C23 0.8(5) . . . . ?
S1 C19 C24 C23 -177.4(3) . . . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd16516
_database_code_depnum_ccdc_archive 'CCDC 1503535'
_audit_update_record             
;
2016-09-09 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Cl N O2 S'
_chemical_formula_weight         437.96

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   13.2671(17)
_cell_length_b                   18.296(3)
_cell_length_c                   19.283(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.684(3)
_cell_angle_gamma                90
_cell_volume                     4434.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2738
_cell_measurement_theta_min      4.597
_cell_measurement_theta_max      42.239

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_T_max  0.7457
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24252
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.575
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             7817
_reflns_number_gt                5176
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0868P)²+2.7371P] 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         7817
_refine_ls_number_parameters     545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1901
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.004
_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 0.21431(9) 0.95921(5) 0.40833(6) 0.0509(3) Uani 1 1 d . . . . .
S2 S 0.25216(9) 0.47625(5) 0.45617(6) 0.0519(3) Uani 1 1 d . . . . .
Cl1 Cl 0.18226(10) 0.97654(7) 0.72990(6) 0.0693(4) Uani 1 1 d . . . . .
Cl2 Cl 0.50001(13) 0.42630(14) 0.71505(10) 0.1402(8) Uani 1 1 d . . . . .
N1 N 0.1253(2) 0.89861(16) 0.41343(16) 0.0445(7) Uani 1 1 d . . . . .
N2 N 0.3096(2) 0.40035(16) 0.44181(16) 0.0431(7) Uani 1 1 d . . . . .
O1 O 0.2284(3) 0.94961(16) 0.33852(15) 0.0670(8) Uani 1 1 d . . . . .
O2 O 0.1786(2) 1.02766(14) 0.42673(17) 0.0646(8) Uani 1 1 d . . . . .
O3 O 0.3355(2) 0.52919(15) 0.48035(18) 0.0678(8) Uani 1 1 d . . . . .
O4 O 0.1656(2) 0.48958(16) 0.39119(16) 0.0688(9) Uani 1 1 d . . . . .
C1 C 0.1465(3) 0.82349(19) 0.40041(19) 0.0403(8) Uani 1 1 d . . . . .
C2 C 0.1410(3) 0.8009(2) 0.3311(2) 0.0506(10) Uani 1 1 d . . . . .
H2 H 0.1210 0.8338 0.2922 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1651(3) 0.7297(2) 0.3194(2) 0.0564(11) Uani 1 1 d . . . . .
H3 H 0.1632 0.7147 0.2729 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1923(3) 0.6804(2) 0.3771(2) 0.0513(10) Uani 1 1 d . . . . .
H4 H 0.2081 0.6322 0.3693 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1959(3) 0.7031(2) 0.4458(2) 0.0441(9) Uani 1 1 d . . . . .
H5 H 0.2143 0.6697 0.4841 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1726(3) 0.77513(19) 0.45941(19) 0.0399(8) Uani 1 1 d . . . . .
C7 C 0.1732(3) 0.80077(19) 0.53205(19) 0.0395(8) Uani 1 1 d . . . . .
C8 C 0.1257(3) 0.8639(2) 0.5376(2) 0.0427(9) Uani 1 1 d . . . . .
C9 C 0.0721(3) 0.9080(2) 0.4696(2) 0.0479(9) Uani 1 1 d . . . . .
H9 H 0.0760 0.9597 0.4834 0.057 Uiso 1 1 calc R U . . .
C10 C -0.0439(3) 0.8873(3) 0.4371(2) 0.0664(12) Uani 1 1 d . . . . .
H10A H -0.0761 0.9162 0.3941 0.100 Uiso 1 1 calc R U . . .
H10B H -0.0797 0.8962 0.4723 0.100 Uiso 1 1 calc R U . . .
H10C H -0.0494 0.8365 0.4242 0.100 Uiso 1 1 calc R U . . .
C11 C 0.1144(3) 0.8921(2) 0.6081(2) 0.0489(10) Uani 1 1 d . . . . .
H11A H 0.0471 0.9177 0.5975 0.059 Uiso 1 1 calc R U . . .
H11B H 0.1129 0.8509 0.6395 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2031(3) 0.9428(2) 0.6484(2) 0.0562(11) Uani 1 1 d . . . . .
H12A H 0.2063 0.9835 0.6169 0.067 Uiso 1 1 calc R U . . .
H12B H 0.2705 0.9170 0.6611 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2227(3) 0.7529(2) 0.5962(2) 0.0452(9) Uani 1 1 d . . . . .
C14 C 0.1641(4) 0.6994(2) 0.6166(2) 0.0587(11) Uani 1 1 d . . . . .
H14 H 0.0925 0.6936 0.5901 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2098(6) 0.6550(3) 0.6751(3) 0.0785(15) Uani 1 1 d . . . . .
H15 H 0.1693 0.6191 0.6879 0.094 Uiso 1 1 calc R U . . .
C16 C 0.3141(6) 0.6629(3) 0.7145(3) 0.0898(19) Uani 1 1 d . . . . .
H16 H 0.3446 0.6328 0.7546 0.108 Uiso 1 1 calc R U . . .
C17 C 0.3751(4) 0.7151(3) 0.6957(3) 0.0820(15) Uani 1 1 d . . . . .
H17 H 0.4468 0.7201 0.7226 0.098 Uiso 1 1 calc R U . . .
C18 C 0.3290(4) 0.7602(3) 0.6366(2) 0.0620(11) Uani 1 1 d . . . . .
H18 H 0.3700 0.7957 0.6239 0.074 Uiso 1 1 calc R U . . .
C19 C 0.3355(3) 0.9365(2) 0.4757(2) 0.0462(9) Uani 1 1 d . . . . .
C20 C 0.3910(3) 0.8755(2) 0.4669(2) 0.0534(10) Uani 1 1 d . . . . .
H20 H 0.3660 0.8474 0.4247 0.064 Uiso 1 1 calc R U . . .
C21 C 0.4835(3) 0.8563(2) 0.5209(2) 0.0547(10) Uani 1 1 d . . . . .
H21 H 0.5199 0.8145 0.5150 0.066 Uiso 1 1 calc R U . . .
C22 C 0.5234(3) 0.8977(2) 0.5835(2) 0.0563(11) Uani 1 1 d . . . . .
C23 C 0.4684(4) 0.9600(2) 0.5896(2) 0.0617(12) Uani 1 1 d . . . . .
H23 H 0.4954 0.9899 0.6303 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3740(3) 0.9792(2) 0.5366(2) 0.0548(11) Uani 1 1 d . . . . .
H24 H 0.3372 1.0208 0.5423 0.066 Uiso 1 1 calc R U . . .
C25 C 0.6238(4) 0.8757(3) 0.6427(3) 0.0829(15) Uani 1 1 d . . . . .
H25A H 0.6630 0.9186 0.6641 0.124 Uiso 1 1 calc R U . . .
H25B H 0.6664 0.8459 0.6220 0.124 Uiso 1 1 calc R U . . .
H25C H 0.6059 0.8485 0.6797 0.124 Uiso 1 1 calc R U . . .
C26 C 0.2435(3) 0.33681(19) 0.42244(19) 0.0388(8) Uani 1 1 d . . . . .
C27 C 0.1659(3) 0.3315(2) 0.3547(2) 0.0514(10) Uani 1 1 d . . . . .
H27 H 0.1545 0.3699 0.3215 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1057(3) 0.2689(3) 0.3369(2) 0.0600(11) Uani 1 1 d . . . . .
H28 H 0.0528 0.2652 0.2917 0.072 Uiso 1 1 calc R U . . .
C29 C 0.1234(3) 0.2117(3) 0.3857(2) 0.0611(12) Uani 1 1 d . . . . .
H29 H 0.0838 0.1690 0.3728 0.073 Uiso 1 1 calc R U . . .
C30 C 0.1996(3) 0.2177(2) 0.4534(2) 0.0503(10) Uani 1 1 d . . . . .
H30 H 0.2100 0.1791 0.4864 0.060 Uiso 1 1 calc R U . . .
C31 C 0.2615(3) 0.28069(19) 0.47341(19) 0.0394(8) Uani 1 1 d . . . . .
C32 C 0.3473(3) 0.28689(19) 0.54370(18) 0.0392(8) Uani 1 1 d . . . . .
C33 C 0.4271(3) 0.3344(2) 0.5494(2) 0.0441(9) Uani 1 1 d . . . . .
C34 C 0.4207(3) 0.3841(2) 0.4861(2) 0.0459(9) Uani 1 1 d . . . . .
H34 H 0.4552 0.4304 0.5060 0.055 Uiso 1 1 calc R U . . .
C35 C 0.4786(3) 0.3527(2) 0.4355(2) 0.0596(11) Uani 1 1 d . . . . .
H35A H 0.4412 0.3103 0.4108 0.089 Uiso 1 1 calc R U . . .
H35B H 0.5497 0.3392 0.4640 0.089 Uiso 1 1 calc R U . . .
H35C H 0.4810 0.3889 0.4000 0.089 Uiso 1 1 calc R U . . .
C36 C 0.5284(3) 0.3364(3) 0.6125(2) 0.0700(13) Uani 1 1 d . . . . .
H36A H 0.5856 0.3200 0.5952 0.084 Uiso 1 1 calc R U . . .
H36B H 0.5224 0.3014 0.6487 0.084 Uiso 1 1 calc R U . . .
C37 C 0.5606(5) 0.4092(4) 0.6505(3) 0.115(2) Uani 1 1 d . . . . .
H37A H 0.5426 0.4479 0.6142 0.138 Uiso 1 1 calc R U . . .
H37B H 0.6372 0.4098 0.6739 0.138 Uiso 1 1 calc R U . . .
C38 C 0.3409(3) 0.2395(2) 0.60571(19) 0.0429(9) Uani 1 1 d . . . . .
C39 C 0.3864(4) 0.1719(2) 0.6214(2) 0.0612(11) Uani 1 1 d . . . . .
H39 H 0.4254 0.1535 0.5930 0.073 Uiso 1 1 calc R U . . .
C40 C 0.3759(4) 0.1304(2) 0.6785(2) 0.0636(12) Uani 1 1 d . . . . .
H40 H 0.4083 0.0848 0.6883 0.076 Uiso 1 1 calc R U . . .
C41 C 0.3187(4) 0.1557(2) 0.7201(2) 0.0619(12) Uani 1 1 d . . . . .
H41 H 0.3105 0.1275 0.7580 0.074 Uiso 1 1 calc R U . . .
C42 C 0.2732(4) 0.2232(3) 0.7060(3) 0.0752(14) Uani 1 1 d . . . . .
H42 H 0.2349 0.2415 0.7350 0.090 Uiso 1 1 calc R U . . .
C43 C 0.2836(4) 0.2647(2) 0.6488(2) 0.0647(12) Uani 1 1 d . . . . .
H43 H 0.2513 0.3104 0.6393 0.078 Uiso 1 1 calc R U . . .
C44 C 0.1985(3) 0.4599(2) 0.5271(2) 0.0470(9) Uani 1 1 d . . . . .
C45 C 0.1017(3) 0.4253(3) 0.5122(2) 0.0616(11) Uani 1 1 d . . . . .
H45 H 0.0640 0.4109 0.4647 0.074 Uiso 1 1 calc R U . . .
C46 C 0.0613(3) 0.4122(3) 0.5686(3) 0.0665(12) Uani 1 1 d . . . . .
H46 H -0.0042 0.3888 0.5583 0.080 Uiso 1 1 calc R U . . .
C47 C 0.1151(3) 0.4327(2) 0.6402(2) 0.0553(10) Uani 1 1 d . . . . .
C48 C 0.2102(4) 0.4677(2) 0.6528(2) 0.0587(11) Uani 1 1 d . . . . .
H48 H 0.2479 0.4823 0.7002 0.070 Uiso 1 1 calc R U . . .
C49 C 0.2520(3) 0.4821(2) 0.5975(2) 0.0568(11) Uani 1 1 d . . . . .
H49 H 0.3163 0.5068 0.6076 0.068 Uiso 1 1 calc R U . . .
C50 C 0.0701(4) 0.4170(3) 0.7005(3) 0.0835(15) Uani 1 1 d . . . . .
H50A H 0.1244 0.4238 0.7469 0.125 Uiso 1 1 calc R U . . .
H50B H 0.0452 0.3674 0.6966 0.125 Uiso 1 1 calc R U . . .
H50C H 0.0120 0.4496 0.6968 0.125 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 1.423(3) . ?
S1 O1 1.428(3) . ?
S1 N1 1.646(3) . ?
S1 C19 1.763(4) . ?
S2 O4 1.423(3) . ?
S2 O3 1.431(3) . ?
S2 N2 1.650(3) . ?
S2 C44 1.758(4) . ?
Cl1 C12 1.790(4) . ?
Cl2 C37 1.713(6) . ?
N1 C1 1.441(4) . ?
N1 C9 1.481(5) . ?
N2 C26 1.432(4) . ?
N2 C34 1.478(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.475(5) . ?
C7 C8 1.336(5) . ?
C7 C13 1.486(5) . ?
C8 C11 1.507(5) . ?
C8 C9 1.509(5) . ?
C9 C10 1.512(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.505(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.383(6) . ?
C13 C14 1.383(5) . ?
C14 C15 1.364(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.367(5) . ?
C19 C20 1.376(5) . ?
C20 C21 1.377(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(6) . ?
C22 C25 1.505(6) . ?
C23 C24 1.385(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.384(5) . ?
C26 C31 1.388(5) . ?
C27 C28 1.376(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.396(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.469(5) . ?
C32 C33 1.346(5) . ?
C32 C38 1.501(5) . ?
C33 C36 1.497(5) . ?
C33 C34 1.504(5) . ?
C34 C35 1.533(5) . ?
C34 H34 0.9800 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.513(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.367(5) . ?
C38 C43 1.373(5) . ?
C39 C40 1.381(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.351(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.363(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.381(6) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C49 1.375(6) . ?
C44 C45 1.378(5) . ?
C45 C46 1.379(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.388(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.366(6) . ?
C47 C50 1.495(6) . ?
C48 C49 1.376(6) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 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 O1 119.85(17) . . ?
O2 S1 N1 105.99(17) . . ?
O1 S1 N1 106.66(17) . . ?
O2 S1 C19 108.77(19) . . ?
O1 S1 C19 107.56(18) . . ?
N1 S1 C19 107.43(16) . . ?
O4 S2 O3 119.46(19) . . ?
O4 S2 N2 106.39(17) . . ?
O3 S2 N2 105.93(17) . . ?
O4 S2 C44 107.51(19) . . ?
O3 S2 C44 108.95(19) . . ?
N2 S2 C44 108.12(16) . . ?
C1 N1 C9 113.8(3) . . ?
C1 N1 S1 116.6(2) . . ?
C9 N1 S1 119.0(2) . . ?
C26 N2 C34 113.7(3) . . ?
C26 N2 S2 116.8(2) . . ?
C34 N2 S2 120.1(2) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 118.3(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 119.8(3) . . ?
C5 C6 C7 123.0(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 C13 122.5(3) . . ?
C6 C7 C13 118.0(3) . . ?
C7 C8 C11 123.6(3) . . ?
C7 C8 C9 119.8(3) . . ?
C11 C8 C9 116.4(3) . . ?
N1 C9 C8 111.8(3) . . ?
N1 C9 C10 109.1(3) . . ?
C8 C9 C10 111.2(3) . . ?
N1 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 112.9(3) . . ?
C12 C11 H11A 109.0 . . ?
C8 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C8 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 Cl1 110.5(3) . . ?
C11 C12 H12A 109.6 . . ?
Cl1 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
Cl1 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C18 C13 C14 118.2(4) . . ?
C18 C13 C7 120.8(3) . . ?
C14 C13 C7 121.0(4) . . ?
C15 C14 C13 121.1(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.4(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.7(5) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C24 C19 C20 120.1(4) . . ?
C24 C19 S1 120.0(3) . . ?
C20 C19 S1 119.9(3) . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 121.3(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 117.6(4) . . ?
C21 C22 C25 121.0(4) . . ?
C23 C22 C25 121.4(4) . . ?
C22 C23 C24 121.7(4) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C19 C24 C23 119.3(4) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 121.6(3) . . ?
C27 C26 N2 120.8(3) . . ?
C31 C26 N2 117.7(3) . . ?
C28 C27 C26 119.4(4) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.1(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 121.0(4) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C26 C31 C30 117.6(3) . . ?
C26 C31 C32 120.2(3) . . ?
C30 C31 C32 122.1(3) . . ?
C33 C32 C31 118.8(3) . . ?
C33 C32 C38 123.5(3) . . ?
C31 C32 C38 117.7(3) . . ?
C32 C33 C36 124.1(4) . . ?
C32 C33 C34 119.1(3) . . ?
C36 C33 C34 116.5(3) . . ?
N2 C34 C33 112.1(3) . . ?
N2 C34 C35 108.5(3) . . ?
C33 C34 C35 112.4(3) . . ?
N2 C34 H34 107.9 . . ?
C33 C34 H34 107.9 . . ?
C35 C34 H34 107.9 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 C37 117.2(4) . . ?
C33 C36 H36A 108.0 . . ?
C37 C36 H36A 108.0 . . ?
C33 C36 H36B 108.0 . . ?
C37 C36 H36B 108.0 . . ?
H36A C36 H36B 107.2 . . ?
C36 C37 Cl2 112.7(4) . . ?
C36 C37 H37A 109.0 . . ?
Cl2 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
Cl2 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C39 C38 C43 117.4(4) . . ?
C39 C38 C32 124.4(3) . . ?
C43 C38 C32 118.2(3) . . ?
C38 C39 C40 121.7(4) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 H39 119.2 . . ?
C41 C40 C39 120.2(4) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 119.3(4) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
C41 C42 C43 120.4(4) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C38 C43 C42 121.0(4) . . ?
C38 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C49 C44 C45 119.6(4) . . ?
C49 C44 S2 120.5(3) . . ?
C45 C44 S2 119.9(3) . . ?
C44 C45 C46 119.2(4) . . ?
C44 C45 H45 120.4 . . ?
C46 C45 H45 120.4 . . ?
C45 C46 C47 122.1(4) . . ?
C45 C46 H46 118.9 . . ?
C47 C46 H46 118.9 . . ?
C48 C47 C46 117.0(4) . . ?
C48 C47 C50 121.9(4) . . ?
C46 C47 C50 121.0(4) . . ?
C47 C48 C49 122.1(4) . . ?
C47 C48 H48 119.0 . . ?
C49 C48 H48 119.0 . . ?
C48 C49 C44 120.0(4) . . ?
C48 C49 H49 120.0 . . ?
C44 C49 H49 120.0 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C1 -177.1(3) . . . . ?
O1 S1 N1 C1 54.1(3) . . . . ?
C19 S1 N1 C1 -61.0(3) . . . . ?
O2 S1 N1 C9 -34.5(3) . . . . ?
O1 S1 N1 C9 -163.3(3) . . . . ?
C19 S1 N1 C9 81.6(3) . . . . ?
O4 S2 N2 C26 -56.6(3) . . . . ?
O3 S2 N2 C26 175.3(3) . . . . ?
C44 S2 N2 C26 58.6(3) . . . . ?
O4 S2 N2 C34 159.1(3) . . . . ?
O3 S2 N2 C34 31.0(3) . . . . ?
C44 S2 N2 C34 -85.7(3) . . . . ?
C9 N1 C1 C2 145.5(3) . . . . ?
S1 N1 C1 C2 -70.0(4) . . . . ?
C9 N1 C1 C6 -34.6(4) . . . . ?
S1 N1 C1 C6 109.9(3) . . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
N1 C1 C2 C3 177.7(4) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
N1 C1 C6 C5 -178.2(3) . . . . ?
C2 C1 C6 C7 -177.4(3) . . . . ?
N1 C1 C6 C7 2.7(5) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C1 C6 C7 C8 15.5(5) . . . . ?
C5 C6 C7 C8 -163.6(3) . . . . ?
C1 C6 C7 C13 -167.4(3) . . . . ?
C5 C6 C7 C13 13.5(5) . . . . ?
C6 C7 C8 C11 175.1(3) . . . . ?
C13 C7 C8 C11 -1.9(6) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C13 C7 C8 C9 -176.9(3) . . . . ?
C1 N1 C9 C8 47.6(4) . . . . ?
S1 N1 C9 C8 -96.0(3) . . . . ?
C1 N1 C9 C10 -75.7(4) . . . . ?
S1 N1 C9 C10 140.7(3) . . . . ?
C7 C8 C9 N1 -31.1(5) . . . . ?
C11 C8 C9 N1 153.5(3) . . . . ?
C7 C8 C9 C10 91.0(4) . . . . ?
C11 C8 C9 C10 -84.3(4) . . . . ?
C7 C8 C11 C12 93.6(4) . . . . ?
C9 C8 C11 C12 -91.3(4) . . . . ?
C8 C11 C12 Cl1 178.1(3) . . . . ?
C8 C7 C13 C18 -91.6(5) . . . . ?
C6 C7 C13 C18 91.4(4) . . . . ?
C8 C7 C13 C14 89.2(5) . . . . ?
C6 C7 C13 C14 -87.8(4) . . . . ?
C18 C13 C14 C15 0.1(6) . . . . ?
C7 C13 C14 C15 179.3(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 -0.6(8) . . . . ?
C15 C16 C17 C18 0.7(8) . . . . ?
C16 C17 C18 C13 -0.3(7) . . . . ?
C14 C13 C18 C17 -0.1(6) . . . . ?
C7 C13 C18 C17 -179.3(4) . . . . ?
O2 S1 C19 C24 5.7(4) . . . . ?
O1 S1 C19 C24 137.0(3) . . . . ?
N1 S1 C19 C24 -108.6(3) . . . . ?
O2 S1 C19 C20 -174.4(3) . . . . ?
O1 S1 C19 C20 -43.2(3) . . . . ?
N1 S1 C19 C20 71.3(3) . . . . ?
C24 C19 C20 C21 2.3(6) . . . . ?
S1 C19 C20 C21 -177.6(3) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C23 -1.3(6) . . . . ?
C20 C21 C22 C25 179.1(4) . . . . ?
C21 C22 C23 C24 2.7(6) . . . . ?
C25 C22 C23 C24 -177.6(4) . . . . ?
C20 C19 C24 C23 -0.9(6) . . . . ?
S1 C19 C24 C23 178.9(3) . . . . ?
C22 C23 C24 C19 -1.7(6) . . . . ?
C34 N2 C26 C27 -143.1(3) . . . . ?
S2 N2 C26 C27 70.4(4) . . . . ?
C34 N2 C26 C31 35.9(4) . . . . ?
S2 N2 C26 C31 -110.6(3) . . . . ?
C31 C26 C27 C28 -0.8(6) . . . . ?
N2 C26 C27 C28 178.2(3) . . . . ?
C26 C27 C28 C29 -0.8(6) . . . . ?
C27 C28 C29 C30 1.8(6) . . . . ?
C28 C29 C30 C31 -1.3(6) . . . . ?
C27 C26 C31 C30 1.3(5) . . . . ?
N2 C26 C31 C30 -177.7(3) . . . . ?
C27 C26 C31 C32 177.6(3) . . . . ?
N2 C26 C31 C32 -1.4(5) . . . . ?
C29 C30 C31 C26 -0.2(5) . . . . ?
C29 C30 C31 C32 -176.5(4) . . . . ?
C26 C31 C32 C33 -20.4(5) . . . . ?
C30 C31 C32 C33 155.7(3) . . . . ?
C26 C31 C32 C38 159.4(3) . . . . ?
C30 C31 C32 C38 -24.4(5) . . . . ?
C31 C32 C33 C36 -168.3(4) . . . . ?
C38 C32 C33 C36 11.8(6) . . . . ?
C31 C32 C33 C34 5.4(5) . . . . ?
C38 C32 C33 C34 -174.4(3) . . . . ?
C26 N2 C34 C33 -48.6(4) . . . . ?
S2 N2 C34 C33 96.7(3) . . . . ?
C26 N2 C34 C35 76.1(4) . . . . ?
S2 N2 C34 C35 -138.6(3) . . . . ?
C32 C33 C34 N2 28.2(5) . . . . ?
C36 C33 C34 N2 -157.5(3) . . . . ?
C32 C33 C34 C35 -94.3(4) . . . . ?
C36 C33 C34 C35 79.9(4) . . . . ?
C32 C33 C36 C37 -127.1(5) . . . . ?
C34 C33 C36 C37 59.0(5) . . . . ?
C33 C36 C37 Cl2 83.7(5) . . . . ?
C33 C32 C38 C39 -87.9(5) . . . . ?
C31 C32 C38 C39 92.3(5) . . . . ?
C33 C32 C38 C43 93.6(5) . . . . ?
C31 C32 C38 C43 -86.2(4) . . . . ?
C43 C38 C39 C40 -0.3(6) . . . . ?
C32 C38 C39 C40 -178.8(4) . . . . ?
C38 C39 C40 C41 0.7(7) . . . . ?
C39 C40 C41 C42 -1.2(7) . . . . ?
C40 C41 C42 C43 1.3(7) . . . . ?
C39 C38 C43 C42 0.4(7) . . . . ?
C32 C38 C43 C42 179.0(4) . . . . ?
C41 C42 C43 C38 -0.9(8) . . . . ?
O4 S2 C44 C49 -145.9(3) . . . . ?
O3 S2 C44 C49 -15.1(4) . . . . ?
N2 S2 C44 C49 99.6(3) . . . . ?
O4 S2 C44 C45 33.4(4) . . . . ?
O3 S2 C44 C45 164.2(3) . . . . ?
N2 S2 C44 C45 -81.1(4) . . . . ?
C49 C44 C45 C46 -1.3(6) . . . . ?
S2 C44 C45 C46 179.3(3) . . . . ?
C44 C45 C46 C47 0.0(7) . . . . ?
C45 C46 C47 C48 0.8(7) . . . . ?
C45 C46 C47 C50 -179.2(4) . . . . ?
C46 C47 C48 C49 -0.2(6) . . . . ?
C50 C47 C48 C49 179.8(4) . . . . ?
C47 C48 C49 C44 -1.2(6) . . . . ?
C45 C44 C49 C48 1.9(6) . . . . ?
S2 C44 C49 C48 -178.8(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
C37 H37B Cl1 0.97 2.80 3.665(5) 149.3 2_646
C34 H34 O3 0.98 2.35 2.873(5) 112.5 .
C9 H9 O2 0.98 2.35 2.868(5) 111.9 .

_refine_diff_density_max         1.547
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



