# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3e
_audit_block_doi                 10.5517/cc1jbsn9
_database_code_depnum_ccdc_archive 'CCDC 1410551'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 Cl N2 O3 S'
_chemical_formula_sum            'C33 H25 Cl N2 O3 S'
_chemical_formula_weight         565.06

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.858(5)
_cell_length_b                   10.060(5)
_cell_length_c                   15.468(8)
_cell_angle_alpha                107.265(15)
_cell_angle_beta                 98.346(15)
_cell_angle_gamma                94.368(16)
_cell_volume                     1437.7(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6025
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19415
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6370
_reflns_number_gt                3675
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.1736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6370
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7126(2) 0.5744(2) 0.40840(15) 0.0429(5) Uani 1 1 d . . .
C2 C 0.6023(3) 0.6076(3) 0.45248(17) 0.0581(7) Uani 1 1 d . . .
H2 H 0.6106 0.6243 0.5156 0.070 Uiso 1 1 calc R . .
C3 C 0.4784(3) 0.6154(3) 0.39982(19) 0.0638(7) Uani 1 1 d . . .
H3 H 0.4028 0.6366 0.4287 0.077 Uiso 1 1 calc R . .
C4 C 0.4625(2) 0.5927(3) 0.30551(18) 0.0547(6) Uani 1 1 d . . .
C5 C 0.3258(3) 0.6041(4) 0.2498(2) 0.0907(11) Uani 1 1 d . . .
H5A H 0.2900 0.5143 0.2056 0.136 Uiso 1 1 calc R . .
H5B H 0.3402 0.6717 0.2183 0.136 Uiso 1 1 calc R . .
H5C H 0.2610 0.6333 0.2903 0.136 Uiso 1 1 calc R . .
C6 C 0.5768(2) 0.5595(2) 0.26206(16) 0.0460(6) Uani 1 1 d . . .
H6 H 0.5691 0.5440 0.1991 0.055 Uiso 1 1 calc R . .
C7 C 0.7013(2) 0.5500(2) 0.31355(14) 0.0387(5) Uani 1 1 d . . .
C8 C 0.8399(2) 0.5162(2) 0.28787(14) 0.0385(5) Uani 1 1 d . . .
C9 C 0.9264(2) 0.5230(2) 0.38017(15) 0.0433(5) Uani 1 1 d . . .
C10 C 0.8390(2) 0.3722(2) 0.21270(14) 0.0391(5) Uani 1 1 d . . .
H10 H 0.9279 0.3377 0.2246 0.047 Uiso 1 1 calc R . .
C11 C 0.7252(2) 0.2650(2) 0.21623(16) 0.0448(6) Uani 1 1 d . . .
C12 C 0.7355(2) 0.2171(2) 0.29926(16) 0.0457(6) Uani 1 1 d . . .
C13 C 0.8597(3) 0.2010(2) 0.34821(17) 0.0532(6) Uani 1 1 d . . .
H13 H 0.9424 0.2266 0.3316 0.064 Uiso 1 1 calc R . .
C14 C 0.8629(3) 0.1473(3) 0.4215(2) 0.0651(7) Uani 1 1 d . . .
H14 H 0.9474 0.1376 0.4531 0.078 Uiso 1 1 calc R . .
C15 C 0.7418(4) 0.1082(3) 0.4477(2) 0.0733(8) Uani 1 1 d . . .
C16 C 0.7464(5) 0.0463(5) 0.5271(3) 0.1197(14) Uani 1 1 d . . .
H16A H 0.6777 0.0814 0.5631 0.180 Uiso 1 1 calc R . .
H16B H 0.8362 0.0728 0.5652 0.180 Uiso 1 1 calc R . .
H16C H 0.7282 -0.0541 0.5029 0.180 Uiso 1 1 calc R . .
C17 C 0.6196(3) 0.1265(3) 0.3995(2) 0.0777(9) Uani 1 1 d . . .
H17 H 0.5373 0.1024 0.4171 0.093 Uiso 1 1 calc R . .
C18 C 0.6134(3) 0.1787(3) 0.32632(18) 0.0598(7) Uani 1 1 d . . .
H18 H 0.5284 0.1883 0.2952 0.072 Uiso 1 1 calc R . .
C19 C 0.9121(2) 0.6158(2) 0.24336(14) 0.0449(6) Uani 1 1 d . . .
H19 H 1.0120 0.6129 0.2550 0.054 Uiso 1 1 calc R . .
C20 C 0.7652(2) 0.7702(3) 0.17259(17) 0.0499(6) Uani 1 1 d . . .
C21 C 0.6845(3) 0.8640(3) 0.1472(2) 0.0627(7) Uani 1 1 d . . .
H21 H 0.6804 0.9509 0.1892 0.075 Uiso 1 1 calc R . .
C22 C 0.6098(3) 0.8266(3) 0.0582(2) 0.0718(8) Uani 1 1 d . . .
H22 H 0.5575 0.8900 0.0400 0.086 Uiso 1 1 calc R . .
C23 C 0.6130(3) 0.6967(3) -0.0029(2) 0.0662(8) Uani 1 1 d . . .
H23 H 0.5614 0.6720 -0.0619 0.079 Uiso 1 1 calc R . .
C24 C 0.6928(2) 0.6011(3) 0.02260(16) 0.0524(6) Uani 1 1 d . . .
H24 H 0.6942 0.5132 -0.0191 0.063 Uiso 1 1 calc R . .
C25 C 0.7699(2) 0.6383(2) 0.11044(15) 0.0426(5) Uani 1 1 d . . .
C26 C 0.8276(2) 0.4051(2) 0.11964(14) 0.0421(5) Uani 1 1 d . . .
H26 H 0.7338 0.3748 0.0841 0.051 Uiso 1 1 calc R . .
C27 C 0.9338(2) 0.3307(3) 0.06463(16) 0.0510(6) Uani 1 1 d . . .
C28 C 0.8910(2) 0.2001(2) -0.01408(15) 0.0451(6) Uani 1 1 d . A .
C29 C 0.7570(3) 0.1393(3) -0.0446(2) 0.0946(12) Uani 1 1 d . . .
H29 H 0.6874 0.1814 -0.0162 0.114 Uiso 1 1 calc R . .
C30 C 0.7235(3) 0.0160(4) -0.1172(3) 0.1258(18) Uani 1 1 d . A .
H30 H 0.6325 -0.0265 -0.1364 0.151 Uiso 1 1 calc R . .
C31 C 0.8260(3) -0.0426(3) -0.1605(2) 0.0787(9) Uani 1 1 d . . .
C32 C 0.9601(3) 0.0149(3) -0.13145(18) 0.0619(7) Uani 1 1 d . A .
H32 H 1.0288 -0.0261 -0.1615 0.074 Uiso 1 1 calc R . .
C33 C 0.9928(2) 0.1342(2) -0.05738(16) 0.0506(6) Uani 1 1 d . . .
H33 H 1.0850 0.1717 -0.0356 0.061 Uiso 1 1 calc R A .
Cl1 Cl 0.7860(8) -0.2098(6) -0.2439(6) 0.089(2) Uani 0.51(5) 1 d P A 1
Cl1' Cl 0.7817(9) -0.176(4) -0.268(2) 0.142(7) Uani 0.49(5) 1 d P A 2
N1 N 0.84794(19) 0.5599(2) 0.44554(12) 0.0480(5) Uani 1 1 d . . .
H1 H 0.8767 0.5730 0.5030 0.058 Uiso 1 1 calc R . .
N2 N 0.86068(19) 0.55686(19) 0.14462(12) 0.0440(5) Uani 1 1 d . . .
O1 O 1.04842(16) 0.49991(18) 0.39065(11) 0.0536(4) Uani 1 1 d . . .
O2 O 0.62594(18) 0.22168(18) 0.15399(12) 0.0613(5) Uani 1 1 d . . .
O3 O 1.05408(19) 0.3790(2) 0.08976(15) 0.0945(8) Uani 1 1 d . . .
S1 S 0.87896(8) 0.79779(7) 0.27785(4) 0.0631(2) 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
C1 C2 1.376(3) . ?
C1 C7 1.400(3) . ?
C1 N1 1.410(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.406(3) . ?
C4 C5 1.522(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.512(3) . ?
C8 C9 1.533(3) . ?
C8 C19 1.558(3) . ?
C8 C10 1.564(3) . ?
C9 O1 1.239(3) . ?
C9 N1 1.344(3) . ?
C10 C11 1.514(3) . ?
C10 C26 1.561(3) . ?
C10 H10 0.9800 . ?
C11 O2 1.219(3) . ?
C11 C12 1.493(3) . ?
C12 C13 1.390(3) . ?
C12 C18 1.395(3) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C17 1.377(4) . ?
C15 C16 1.531(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.461(3) . ?
C19 S1 1.818(3) . ?
C19 H19 0.9800 . ?
C20 C21 1.386(4) . ?
C20 C25 1.397(3) . ?
C20 S1 1.772(3) . ?
C21 C22 1.392(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 N2 1.408(3) . ?
C26 N2 1.457(3) . ?
C26 C27 1.543(3) . ?
C26 H26 0.9800 . ?
C27 O3 1.208(3) . ?
C27 C28 1.484(3) . ?
C28 C29 1.366(3) . ?
C28 C33 1.389(3) . ?
C29 C30 1.383(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.367(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.357(4) . ?
C31 Cl1 1.764(7) . ?
C31 Cl1' 1.768(10) . ?
C32 C33 1.369(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
N1 H1 0.8600 . ?

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
C2 C1 C7 121.4(2) . . ?
C2 C1 N1 129.1(2) . . ?
C7 C1 N1 109.56(19) . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C6 118.4(2) . . ?
C3 C4 C5 121.5(2) . . ?
C6 C4 C5 120.1(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 119.7(2) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
C6 C7 C1 119.9(2) . . ?
C6 C7 C8 132.39(19) . . ?
C1 C7 C8 107.70(18) . . ?
C7 C8 C9 102.67(17) . . ?
C7 C8 C19 116.34(18) . . ?
C9 C8 C19 110.82(17) . . ?
C7 C8 C10 115.94(16) . . ?
C9 C8 C10 111.75(18) . . ?
C19 C8 C10 99.66(16) . . ?
O1 C9 N1 127.2(2) . . ?
O1 C9 C8 124.5(2) . . ?
N1 C9 C8 108.26(19) . . ?
C11 C10 C26 114.75(18) . . ?
C11 C10 C8 110.93(17) . . ?
C26 C10 C8 105.62(17) . . ?
C11 C10 H10 108.4 . . ?
C26 C10 H10 108.4 . . ?
C8 C10 H10 108.4 . . ?
O2 C11 C12 120.8(2) . . ?
O2 C11 C10 120.9(2) . . ?
C12 C11 C10 118.3(2) . . ?
C13 C12 C18 117.9(2) . . ?
C13 C12 C11 123.7(2) . . ?
C18 C12 C11 118.3(2) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C17 C15 C14 117.5(3) . . ?
C17 C15 C16 122.4(3) . . ?
C14 C15 C16 120.2(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 123.1(3) . . ?
C15 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C12 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C12 C18 H18 120.3 . . ?
N2 C19 C8 105.51(17) . . ?
N2 C19 S1 107.26(15) . . ?
C8 C19 S1 117.05(15) . . ?
N2 C19 H19 108.9 . . ?
C8 C19 H19 108.9 . . ?
S1 C19 H19 108.9 . . ?
C21 C20 C25 120.7(2) . . ?
C21 C20 S1 127.8(2) . . ?
C25 C20 S1 111.41(19) . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C20 119.5(2) . . ?
C24 C25 N2 126.2(2) . . ?
C20 C25 N2 114.3(2) . . ?
N2 C26 C27 110.28(18) . . ?
N2 C26 C10 105.45(16) . . ?
C27 C26 C10 109.29(18) . . ?
N2 C26 H26 110.6 . . ?
C27 C26 H26 110.6 . . ?
C10 C26 H26 110.6 . . ?
O3 C27 C28 120.8(2) . . ?
O3 C27 C26 117.9(2) . . ?
C28 C27 C26 121.3(2) . . ?
C29 C28 C33 118.2(2) . . ?
C29 C28 C27 123.4(2) . . ?
C33 C28 C27 118.3(2) . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 119.1(3) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C32 C31 C30 121.4(3) . . ?
C32 C31 Cl1 119.2(3) . . ?
C30 C31 Cl1 118.7(3) . . ?
C32 C31 Cl1' 118.2(4) . . ?
C30 C31 Cl1' 119.4(4) . . ?
Cl1 C31 Cl1' 18.8(16) . . ?
C31 C32 C33 119.1(2) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C28 121.3(2) . . ?
C32 C33 H33 119.4 . . ?
C28 C33 H33 119.4 . . ?
C9 N1 C1 111.76(18) . . ?
C9 N1 H1 124.1 . . ?
C1 N1 H1 124.1 . . ?
C25 N2 C26 121.06(18) . . ?
C25 N2 C19 113.12(18) . . ?
C26 N2 C19 109.94(17) . . ?
C20 S1 C19 91.38(11) . . ?

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
N1 H1 O1 0.86 2.06 2.841(3) 151.1 2_766

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_3l
_audit_block_doi                 10.5517/cc1jbspb
_database_code_depnum_ccdc_archive 'CCDC 1410552'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H28 Cl2 N2 O3 S'
_chemical_formula_sum            'C39 H28 Cl2 N2 O3 S'
_chemical_formula_weight         675.59

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7690(11)
_cell_length_b                   13.1644(13)
_cell_length_c                   14.4577(14)
_cell_angle_alpha                68.080(3)
_cell_angle_beta                 77.970(3)
_cell_angle_gamma                75.448(3)
_cell_volume                     1655.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9323
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      2.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25338
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.63
_reflns_number_total             7625
_reflns_number_gt                4925
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.3374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7625
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8108(3) 0.03326(19) 0.04123(19) 0.0554(6) Uani 1 1 d . . .
H1 H 0.8791 -0.0254 0.0739 0.066 Uiso 1 1 calc R . .
C2 C 0.7179(3) 0.0132(2) -0.0068(2) 0.0667(7) Uani 1 1 d . . .
H2 H 0.7247 -0.0585 -0.0071 0.080 Uiso 1 1 calc R . .
C3 C 0.6159(3) 0.0979(2) -0.05390(19) 0.0605(7) Uani 1 1 d . . .
H3 H 0.5541 0.0843 -0.0870 0.073 Uiso 1 1 calc R . .
C4 C 0.6050(3) 0.2025(2) -0.05234(18) 0.0575(6) Uani 1 1 d . . .
H4 H 0.5341 0.2601 -0.0830 0.069 Uiso 1 1 calc R . .
C5 C 0.6990(3) 0.22312(18) -0.00529(16) 0.0508(6) Uani 1 1 d . . .
H5 H 0.6914 0.2950 -0.0053 0.061 Uiso 1 1 calc R . .
C6 C 0.8043(2) 0.13885(17) 0.04174(14) 0.0411(5) Uani 1 1 d . . .
C7 C 0.9105(2) 0.16254(19) 0.08896(16) 0.0488(5) Uani 1 1 d . . .
H7A H 0.9564 0.0929 0.1345 0.059 Uiso 1 1 calc R . .
H7B H 0.9836 0.1940 0.0368 0.059 Uiso 1 1 calc R . .
C8 C 0.8437(2) 0.35092(17) 0.10450(15) 0.0409(5) Uani 1 1 d . . .
C9 C 0.7632(2) 0.40197(16) 0.18479(14) 0.0366(4) Uani 1 1 d . . .
C10 C 0.7214(2) 0.30287(16) 0.27085(14) 0.0362(4) Uani 1 1 d . . .
C11 C 0.6452(2) 0.29199(17) 0.36492(14) 0.0420(5) Uani 1 1 d . . .
H11 H 0.6125 0.3531 0.3866 0.050 Uiso 1 1 calc R . .
C12 C 0.6191(3) 0.18713(19) 0.42601(15) 0.0496(6) Uani 1 1 d . . .
C13 C 0.6694(3) 0.09505(19) 0.39703(17) 0.0576(6) Uani 1 1 d . . .
H13 H 0.6508 0.0258 0.4402 0.069 Uiso 1 1 calc R . .
C14 C 0.7480(3) 0.10509(18) 0.30318(17) 0.0531(6) Uani 1 1 d . . .
H14 H 0.7831 0.0433 0.2826 0.064 Uiso 1 1 calc R . .
C15 C 0.7722(2) 0.20887(17) 0.24185(14) 0.0401(5) Uani 1 1 d . . .
C16 C 0.8527(2) 0.46953(16) 0.20873(14) 0.0367(4) Uani 1 1 d . . .
H16 H 0.9131 0.5042 0.1473 0.044 Uiso 1 1 calc R . .
C17 C 0.9473(2) 0.39604(17) 0.28955(15) 0.0409(5) Uani 1 1 d . . .
C18 C 1.0665(2) 0.31178(17) 0.26535(15) 0.0401(5) Uani 1 1 d . . .
C19 C 1.1406(2) 0.32668(19) 0.16949(16) 0.0492(5) Uani 1 1 d . . .
H19 H 1.1126 0.3906 0.1162 0.059 Uiso 1 1 calc R . .
C20 C 1.2556(3) 0.2468(2) 0.15326(17) 0.0547(6) Uani 1 1 d . . .
H20 H 1.3047 0.2581 0.0889 0.066 Uiso 1 1 calc R . .
C21 C 1.2994(3) 0.1506(2) 0.23009(17) 0.0545(6) Uani 1 1 d . . .
C22 C 1.4264(3) 0.0645(3) 0.2121(2) 0.0858(9) Uani 1 1 d . . .
H22A H 1.4546 0.0811 0.1411 0.129 Uiso 1 1 calc R . .
H22B H 1.4016 -0.0081 0.2409 0.129 Uiso 1 1 calc R . .
H22C H 1.5040 0.0655 0.2428 0.129 Uiso 1 1 calc R . .
C23 C 1.2223(3) 0.1353(2) 0.32510(18) 0.0625(7) Uani 1 1 d . . .
H23 H 1.2484 0.0700 0.3776 0.075 Uiso 1 1 calc R . .
C24 C 1.1089(3) 0.21404(19) 0.34334(16) 0.0539(6) Uani 1 1 d . . .
H24 H 1.0602 0.2023 0.4079 0.065 Uiso 1 1 calc R . .
C25 C 0.6385(2) 0.49727(17) 0.14091(15) 0.0420(5) Uani 1 1 d . . .
H25 H 0.6710 0.5404 0.0716 0.050 Uiso 1 1 calc R . .
C26 C 0.3987(2) 0.49676(19) 0.25152(17) 0.0506(6) Uani 1 1 d . . .
C27 C 0.2744(3) 0.4749(2) 0.3134(2) 0.0692(7) Uani 1 1 d . . .
H27 H 0.2183 0.4351 0.3007 0.083 Uiso 1 1 calc R . .
C28 C 0.2333(3) 0.5121(3) 0.3943(2) 0.0784(8) Uani 1 1 d . . .
H28 H 0.1488 0.4978 0.4359 0.094 Uiso 1 1 calc R . .
C29 C 0.3162(3) 0.5698(2) 0.4136(2) 0.0706(7) Uani 1 1 d . . .
H29 H 0.2877 0.5946 0.4684 0.085 Uiso 1 1 calc R . .
C30 C 0.4426(3) 0.5917(2) 0.35196(18) 0.0563(6) Uani 1 1 d . . .
H30 H 0.4984 0.6314 0.3650 0.068 Uiso 1 1 calc R . .
C31 C 0.4848(2) 0.55421(17) 0.27147(16) 0.0435(5) Uani 1 1 d . . .
C32 C 0.7408(2) 0.56277(16) 0.23877(14) 0.0379(5) Uani 1 1 d . . .
H32 H 0.7262 0.5442 0.3119 0.045 Uiso 1 1 calc R . .
C33 C 0.7972(2) 0.67138(17) 0.18751(16) 0.0429(5) Uani 1 1 d . . .
C34 C 0.8755(2) 0.70734(16) 0.24398(15) 0.0423(5) Uani 1 1 d . . .
C35 C 0.8324(3) 0.7019(3) 0.3425(2) 0.0729(8) Uani 1 1 d . . .
H35 H 0.7568 0.6667 0.3789 0.087 Uiso 1 1 calc R . .
C36 C 0.8996(3) 0.7478(3) 0.3877(2) 0.0896(11) Uani 1 1 d . . .
H36 H 0.8674 0.7466 0.4533 0.108 Uiso 1 1 calc R . .
C37 C 1.0141(3) 0.7951(2) 0.33493(19) 0.0630(7) Uani 1 1 d . . .
C38 C 1.0639(3) 0.7959(2) 0.24021(19) 0.0721(8) Uani 1 1 d . . .
H38 H 1.1442 0.8260 0.2060 0.087 Uiso 1 1 calc R . .
C39 C 0.9945(3) 0.7517(2) 0.19485(17) 0.0653(7) Uani 1 1 d . . .
H39 H 1.0289 0.7519 0.1298 0.078 Uiso 1 1 calc R . .
Cl1 Cl 0.51727(9) 0.17300(6) 0.54291(5) 0.0810(3) Uani 1 1 d . . .
Cl2 Cl 1.09870(11) 0.85532(9) 0.38968(7) 0.1066(3) Uani 1 1 d . . .
N1 N 0.84645(19) 0.23902(14) 0.14393(12) 0.0432(4) Uani 1 1 d . . .
N2 N 0.60925(18) 0.56830(14) 0.20303(12) 0.0401(4) Uani 1 1 d . . .
O1 O 0.89279(17) 0.40127(13) 0.01989(10) 0.0523(4) Uani 1 1 d . . .
O2 O 0.92135(18) 0.40433(14) 0.37292(11) 0.0577(4) Uani 1 1 d . . .
O3 O 0.7863(2) 0.72276(13) 0.09944(12) 0.0643(5) Uani 1 1 d . . .
S1 S 0.47183(7) 0.45924(5) 0.14384(5) 0.05734(19) 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
C1 C2 1.377(4) . ?
C1 C6 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(3) . ?
C7 N1 1.453(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.215(2) . ?
C8 N1 1.362(3) . ?
C8 C9 1.534(3) . ?
C9 C10 1.503(3) . ?
C9 C25 1.556(3) . ?
C9 C16 1.556(3) . ?
C10 C11 1.382(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 Cl1 1.743(2) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.409(2) . ?
C16 C17 1.520(3) . ?
C16 C32 1.554(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.219(2) . ?
C17 C18 1.477(3) . ?
C18 C19 1.390(3) . ?
C18 C24 1.394(3) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.390(3) . ?
C21 C22 1.507(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.370(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.466(3) . ?
C25 S1 1.808(2) . ?
C25 H25 0.9800 . ?
C26 C27 1.374(3) . ?
C26 C31 1.395(3) . ?
C26 S1 1.764(3) . ?
C27 C28 1.380(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.376(3) . ?
C30 H30 0.9300 . ?
C31 N2 1.402(3) . ?
C32 N2 1.458(2) . ?
C32 C33 1.527(3) . ?
C32 H32 0.9800 . ?
C33 O3 1.211(2) . ?
C33 C34 1.485(3) . ?
C34 C39 1.373(3) . ?
C34 C35 1.378(3) . ?
C35 C36 1.378(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.364(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.351(4) . ?
C37 Cl2 1.734(2) . ?
C38 C39 1.378(3) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?

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
C2 C1 C6 121.1(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 121.4(2) . . ?
C5 C6 C7 120.96(19) . . ?
N1 C7 C6 112.99(17) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 125.89(19) . . ?
O1 C8 C9 126.36(19) . . ?
N1 C8 C9 107.71(16) . . ?
C10 C9 C8 103.07(16) . . ?
C10 C9 C25 116.10(16) . . ?
C8 C9 C25 109.72(15) . . ?
C10 C9 C16 115.90(15) . . ?
C8 C9 C16 112.40(16) . . ?
C25 C9 C16 99.93(15) . . ?
C11 C10 C15 119.48(18) . . ?
C11 C10 C9 132.49(18) . . ?
C15 C10 C9 108.02(16) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 Cl1 119.23(17) . . ?
C11 C12 Cl1 118.54(18) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 117.9(2) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 122.30(19) . . ?
C14 C15 N1 127.8(2) . . ?
C10 C15 N1 109.87(17) . . ?
C17 C16 C32 113.53(16) . . ?
C17 C16 C9 112.05(15) . . ?
C32 C16 C9 104.71(15) . . ?
C17 C16 H16 108.8 . . ?
C32 C16 H16 108.8 . . ?
C9 C16 H16 108.8 . . ?
O2 C17 C18 121.38(18) . . ?
O2 C17 C16 120.43(19) . . ?
C18 C17 C16 118.14(17) . . ?
C19 C18 C24 118.7(2) . . ?
C19 C18 C17 123.23(19) . . ?
C24 C18 C17 118.06(19) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C23 117.8(2) . . ?
C20 C21 C22 121.3(2) . . ?
C23 C21 C22 120.9(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 121.7(2) . . ?
C24 C23 H23 119.1 . . ?
C21 C23 H23 119.1 . . ?
C23 C24 C18 120.1(2) . . ?
C23 C24 H24 120.0 . . ?
C18 C24 H24 120.0 . . ?
N2 C25 C9 104.85(15) . . ?
N2 C25 S1 106.93(14) . . ?
C9 C25 S1 117.78(14) . . ?
N2 C25 H25 109.0 . . ?
C9 C25 H25 109.0 . . ?
S1 C25 H25 109.0 . . ?
C27 C26 C31 120.3(2) . . ?
C27 C26 S1 127.90(19) . . ?
C31 C26 S1 111.77(17) . . ?
C26 C27 C28 119.7(2) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.3(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 119.6(2) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C26 119.6(2) . . ?
C30 C31 N2 126.6(2) . . ?
C26 C31 N2 113.75(19) . . ?
N2 C32 C33 111.87(16) . . ?
N2 C32 C16 106.14(15) . . ?
C33 C32 C16 107.63(16) . . ?
N2 C32 H32 110.4 . . ?
C33 C32 H32 110.4 . . ?
C16 C32 H32 110.4 . . ?
O3 C33 C34 120.88(18) . . ?
O3 C33 C32 119.50(18) . . ?
C34 C33 C32 119.42(17) . . ?
C39 C34 C35 118.0(2) . . ?
C39 C34 C33 118.50(19) . . ?
C35 C34 C33 123.45(19) . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C37 C36 C35 119.0(2) . . ?
C37 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C38 C37 C36 121.3(2) . . ?
C38 C37 Cl2 118.91(19) . . ?
C36 C37 Cl2 119.8(2) . . ?
C37 C38 C39 119.3(2) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C34 C39 C38 121.2(2) . . ?
C34 C39 H39 119.4 . . ?
C38 C39 H39 119.4 . . ?
C8 N1 C15 111.29(17) . . ?
C8 N1 C7 123.81(17) . . ?
C15 N1 C7 124.80(17) . . ?
C31 N2 C32 119.40(16) . . ?
C31 N2 C25 112.52(16) . . ?
C32 N2 C25 109.17(16) . . ?
C26 S1 C25 90.94(10) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_3n
_audit_block_doi                 10.5517/cc1jbsqc
_database_code_depnum_ccdc_archive 'CCDC 1410553'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H25 Cl3 N2 O3 S'
_chemical_formula_sum            'C38 H25 Cl3 N2 O3 S'
_chemical_formula_weight         696.01

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7111(10)
_cell_length_b                   13.1409(15)
_cell_length_c                   14.4778(16)
_cell_angle_alpha                68.243(3)
_cell_angle_beta                 77.852(3)
_cell_angle_gamma                74.805(3)
_cell_volume                     1642.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8270
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   sadabs


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23783
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.61
_reflns_number_total             7507
_reflns_number_gt                4639
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.5570P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7507
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3118(3) 0.5307(2) 0.0382(2) 0.0566(7) Uani 1 1 d . . .
H1 H 0.3808 0.4716 0.0710 0.068 Uiso 1 1 calc R . .
C2 C 0.2190(3) 0.5107(3) -0.0095(2) 0.0660(8) Uani 1 1 d . . .
H2 H 0.2259 0.4388 -0.0096 0.079 Uiso 1 1 calc R . .
C3 C 0.1165(3) 0.5965(3) -0.0568(2) 0.0649(8) Uani 1 1 d . . .
H3 H 0.0540 0.5832 -0.0896 0.078 Uiso 1 1 calc R . .
C4 C 0.1054(3) 0.7019(2) -0.0562(2) 0.0589(7) Uani 1 1 d . . .
H4 H 0.0344 0.7601 -0.0877 0.071 Uiso 1 1 calc R . .
C5 C 0.1998(3) 0.7222(2) -0.00892(18) 0.0512(6) Uani 1 1 d . . .
H5 H 0.1922 0.7944 -0.0092 0.061 Uiso 1 1 calc R . .
C6 C 0.3045(2) 0.63729(19) 0.03855(16) 0.0410(5) Uani 1 1 d . . .
C7 C 0.4120(3) 0.6603(2) 0.08573(18) 0.0485(6) Uani 1 1 d . . .
H7A H 0.4587 0.5902 0.1309 0.058 Uiso 1 1 calc R . .
H7B H 0.4853 0.6914 0.0336 0.058 Uiso 1 1 calc R . .
C8 C 0.3456(2) 0.8488(2) 0.10319(17) 0.0408(5) Uani 1 1 d . . .
C9 C 0.2659(2) 0.89978(18) 0.18429(15) 0.0367(5) Uani 1 1 d . . .
C10 C 0.2250(2) 0.79994(18) 0.26951(16) 0.0364(5) Uani 1 1 d . . .
C11 C 0.1501(2) 0.78873(19) 0.36411(16) 0.0408(5) Uani 1 1 d . . .
H11 H 0.1183 0.8496 0.3867 0.049 Uiso 1 1 calc R . .
C12 C 0.1241(3) 0.6841(2) 0.42397(17) 0.0481(6) Uani 1 1 d . . .
C13 C 0.1715(3) 0.5927(2) 0.39283(19) 0.0578(7) Uani 1 1 d . . .
H13 H 0.1518 0.5236 0.4349 0.069 Uiso 1 1 calc R . .
C14 C 0.2489(3) 0.6032(2) 0.29866(19) 0.0535(7) Uani 1 1 d . . .
H14 H 0.2827 0.5418 0.2768 0.064 Uiso 1 1 calc R . .
C15 C 0.2737(2) 0.70665(19) 0.23913(16) 0.0393(5) Uani 1 1 d . . .
C16 C 0.3566(2) 0.96661(18) 0.20796(16) 0.0365(5) Uani 1 1 d . . .
H16 H 0.4166 1.0013 0.1465 0.044 Uiso 1 1 calc R . .
C17 C 0.4531(2) 0.89204(19) 0.28766(17) 0.0402(5) Uani 1 1 d . . .
C18 C 0.5752(2) 0.80730(19) 0.26240(16) 0.0404(5) Uani 1 1 d . . .
C19 C 0.6215(3) 0.7106(2) 0.33936(18) 0.0555(7) Uani 1 1 d . . .
H19 H 0.5729 0.6991 0.4039 0.067 Uiso 1 1 calc R . .
C20 C 0.7378(3) 0.6319(2) 0.3217(2) 0.0639(8) Uani 1 1 d . . .
H20 H 0.7673 0.5667 0.3736 0.077 Uiso 1 1 calc R . .
C21 C 0.8107(3) 0.6503(2) 0.2262(2) 0.0541(7) Uani 1 1 d . . .
C22 C 0.7665(3) 0.7436(2) 0.14815(19) 0.0548(7) Uani 1 1 d . . .
H22 H 0.8154 0.7541 0.0838 0.066 Uiso 1 1 calc R . .
C23 C 0.6486(3) 0.8220(2) 0.16618(18) 0.0500(6) Uani 1 1 d . . .
H23 H 0.6175 0.8856 0.1134 0.060 Uiso 1 1 calc R . .
C24 C 0.2444(2) 1.06035(18) 0.23963(17) 0.0383(5) Uani 1 1 d . . .
H24 H 0.2312 1.0414 0.3126 0.046 Uiso 1 1 calc R . .
C25 C 0.3001(3) 1.1685(2) 0.18868(18) 0.0436(6) Uani 1 1 d . . .
C26 C 0.3754(2) 1.20653(19) 0.24544(17) 0.0426(5) Uani 1 1 d . . .
C27 C 0.4952(3) 1.2507(2) 0.1984(2) 0.0624(8) Uani 1 1 d . . .
H27 H 0.5315 1.2507 0.1336 0.075 Uiso 1 1 calc R . .
C28 C 0.5628(3) 1.2951(3) 0.2445(2) 0.0703(9) Uani 1 1 d . . .
H28 H 0.6447 1.3238 0.2117 0.084 Uiso 1 1 calc R . .
C29 C 0.5084(3) 1.2964(2) 0.3386(2) 0.0604(7) Uani 1 1 d . . .
C30 C 0.3935(4) 1.2494(3) 0.3897(2) 0.0827(10) Uani 1 1 d . . .
H30 H 0.3591 1.2487 0.4549 0.099 Uiso 1 1 calc R . .
C31 C 0.3287(3) 1.2027(3) 0.3436(2) 0.0701(9) Uani 1 1 d . . .
H31 H 0.2523 1.1681 0.3791 0.084 Uiso 1 1 calc R . .
C32 C 0.1394(2) 0.99648(19) 0.14185(17) 0.0413(5) Uani 1 1 d . . .
H32 H 0.1712 1.0400 0.0728 0.050 Uiso 1 1 calc R . .
C33 C -0.0145(2) 1.05370(19) 0.27332(18) 0.0432(6) Uani 1 1 d . . .
C34 C -0.0559(3) 1.0915(2) 0.3540(2) 0.0556(7) Uani 1 1 d . . .
H34 H 0.0009 1.1304 0.3672 0.067 Uiso 1 1 calc R . .
C35 C -0.1830(3) 1.0710(3) 0.4149(2) 0.0684(8) Uani 1 1 d . . .
H35 H -0.2117 1.0966 0.4693 0.082 Uiso 1 1 calc R . .
C36 C -0.2672(3) 1.0135(3) 0.3962(2) 0.0748(9) Uani 1 1 d . . .
H36 H -0.3517 0.9995 0.4383 0.090 Uiso 1 1 calc R . .
C37 C -0.2267(3) 0.9765(3) 0.3149(2) 0.0677(8) Uani 1 1 d . . .
H37 H -0.2839 0.9379 0.3018 0.081 Uiso 1 1 calc R . .
C38 C -0.1014(3) 0.9970(2) 0.25376(19) 0.0503(6) Uani 1 1 d . . .
Cl1 Cl 0.02526(10) 0.66877(7) 0.54195(5) 0.0778(3) Uani 1 1 d . . .
Cl2 Cl 0.96228(9) 0.55216(7) 0.20486(6) 0.0809(3) Uani 1 1 d . . .
Cl3 Cl 0.59000(12) 1.35724(9) 0.39487(7) 0.1016(3) Uani 1 1 d . . .
N1 N 0.3476(2) 0.73722(16) 0.14112(14) 0.0432(5) Uani 1 1 d . . .
N2 N 0.11088(19) 1.06678(15) 0.20495(14) 0.0402(4) Uani 1 1 d . . .
O1 O 0.39402(18) 0.90016(15) 0.01894(12) 0.0525(4) Uani 1 1 d . . .
O2 O 0.42920(19) 0.89902(15) 0.37122(13) 0.0571(5) Uani 1 1 d . . .
O3 O 0.2907(2) 1.21884(15) 0.10042(13) 0.0617(5) Uani 1 1 d . . .
S1 S -0.02906(7) 0.95946(6) 0.14534(5) 0.0575(2) 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
C1 C2 1.370(4) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(3) . ?
C7 N1 1.454(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.216(3) . ?
C8 N1 1.358(3) . ?
C8 C9 1.535(3) . ?
C9 C10 1.506(3) . ?
C9 C32 1.556(3) . ?
C9 C16 1.556(3) . ?
C10 C11 1.383(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 Cl1 1.742(2) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.411(3) . ?
C16 C17 1.518(3) . ?
C16 C24 1.556(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.216(3) . ?
C17 C18 1.486(3) . ?
C18 C19 1.386(3) . ?
C18 C23 1.393(3) . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(4) . ?
C21 Cl2 1.742(3) . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N2 1.458(3) . ?
C24 C25 1.522(3) . ?
C24 H24 0.9800 . ?
C25 O3 1.212(3) . ?
C25 C26 1.486(3) . ?
C26 C27 1.371(3) . ?
C26 C31 1.384(4) . ?
C27 C28 1.375(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.358(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.360(4) . ?
C29 Cl3 1.738(3) . ?
C30 C31 1.378(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 N2 1.466(3) . ?
C32 S1 1.811(2) . ?
C32 H32 0.9800 . ?
C33 C34 1.378(3) . ?
C33 C38 1.391(3) . ?
C33 N2 1.403(3) . ?
C34 C35 1.384(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.372(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.381(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.370(4) . ?
C37 H37 0.9300 . ?
C38 S1 1.769(3) . ?

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
C2 C1 C6 121.1(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C7 120.9(2) . . ?
C1 C6 C7 121.1(2) . . ?
N1 C7 C6 113.13(19) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 126.3(2) . . ?
O1 C8 C9 125.8(2) . . ?
N1 C8 C9 107.83(18) . . ?
C10 C9 C8 102.74(18) . . ?
C10 C9 C32 116.22(18) . . ?
C8 C9 C32 109.68(17) . . ?
C10 C9 C16 116.30(17) . . ?
C8 C9 C16 112.52(17) . . ?
C32 C9 C16 99.67(17) . . ?
C11 C10 C15 119.5(2) . . ?
C11 C10 C9 132.2(2) . . ?
C15 C10 C9 108.26(18) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 Cl1 119.10(19) . . ?
C11 C12 Cl1 118.73(19) . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 122.6(2) . . ?
C14 C15 N1 127.7(2) . . ?
C10 C15 N1 109.76(19) . . ?
C17 C16 C24 113.21(18) . . ?
C17 C16 C9 111.93(17) . . ?
C24 C16 C9 104.95(17) . . ?
C17 C16 H16 108.9 . . ?
C24 C16 H16 108.9 . . ?
C9 C16 H16 108.9 . . ?
O2 C17 C18 120.4(2) . . ?
O2 C17 C16 121.1(2) . . ?
C18 C17 C16 118.46(19) . . ?
C19 C18 C23 118.5(2) . . ?
C19 C18 C17 118.1(2) . . ?
C23 C18 C17 123.4(2) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.3(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 Cl2 119.4(2) . . ?
C20 C21 Cl2 119.2(2) . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
N2 C24 C25 111.86(18) . . ?
N2 C24 C16 105.85(17) . . ?
C25 C24 C16 107.64(18) . . ?
N2 C24 H24 110.5 . . ?
C25 C24 H24 110.5 . . ?
C16 C24 H24 110.5 . . ?
O3 C25 C26 120.7(2) . . ?
O3 C25 C24 119.5(2) . . ?
C26 C25 C24 119.7(2) . . ?
C27 C26 C31 117.5(2) . . ?
C27 C26 C25 119.1(2) . . ?
C31 C26 C25 123.3(2) . . ?
C26 C27 C28 121.7(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C29 C28 C27 119.1(2) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 121.3(3) . . ?
C28 C29 Cl3 119.0(2) . . ?
C30 C29 Cl3 119.7(2) . . ?
C29 C30 C31 119.1(3) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C30 C31 C26 121.1(3) . . ?
C30 C31 H31 119.4 . . ?
C26 C31 H31 119.4 . . ?
N2 C32 C9 104.81(17) . . ?
N2 C32 S1 106.98(15) . . ?
C9 C32 S1 117.58(15) . . ?
N2 C32 H32 109.1 . . ?
C9 C32 H32 109.1 . . ?
S1 C32 H32 109.1 . . ?
C34 C33 C38 119.7(2) . . ?
C34 C33 N2 126.3(2) . . ?
C38 C33 N2 114.0(2) . . ?
C33 C34 C35 119.1(3) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 119.4(3) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C33 120.7(3) . . ?
C37 C38 S1 127.5(2) . . ?
C33 C38 S1 111.78(18) . . ?
C8 N1 C15 111.36(18) . . ?
C8 N1 C7 124.12(19) . . ?
C15 N1 C7 124.46(19) . . ?
C33 N2 C24 119.91(18) . . ?
C33 N2 C32 112.58(18) . . ?
C24 N2 C32 109.25(17) . . ?
C38 S1 C32 90.81(11) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_3q
_audit_block_doi                 10.5517/cc1jbsrd
_database_code_depnum_ccdc_archive 'CCDC 1410554'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H31 Cl N2 O4 S'
_chemical_formula_sum            'C40 H31 Cl N2 O4 S'
_chemical_formula_weight         671.18

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0080(12)
_cell_length_b                   13.0276(14)
_cell_length_c                   14.4607(16)
_cell_angle_alpha                69.088(3)
_cell_angle_beta                 75.860(3)
_cell_angle_gamma                75.069(3)
_cell_volume                     1677.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25538
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.59
_reflns_number_total             7654
_reflns_number_gt                5216
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0670P)²+0.2914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7654
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51821(19) -0.05528(15) 0.22859(14) 0.0406(4) Uani 1 1 d . . .
C2 C 0.5643(2) -0.09730(18) 0.14898(16) 0.0530(5) Uani 1 1 d . . .
H2 H 0.5094 -0.1359 0.1350 0.064 Uiso 1 1 calc R . .
C3 C 0.6941(2) -0.0810(2) 0.08990(18) 0.0683(7) Uani 1 1 d . . .
H3 H 0.7255 -0.1086 0.0357 0.082 Uiso 1 1 calc R . .
C4 C 0.7762(3) -0.0254(2) 0.1100(2) 0.0753(7) Uani 1 1 d . . .
H4 H 0.8630 -0.0159 0.0698 0.090 Uiso 1 1 calc R . .
C5 C 0.7315(2) 0.0169(2) 0.1897(2) 0.0661(6) Uani 1 1 d . . .
H5 H 0.7873 0.0551 0.2033 0.079 Uiso 1 1 calc R . .
C6 C 0.6021(2) 0.00169(16) 0.24903(16) 0.0478(5) Uani 1 1 d . . .
C7 C 0.36099(19) 0.00537(15) 0.35944(14) 0.0395(4) Uani 1 1 d . . .
H7 H 0.3275 -0.0376 0.4287 0.047 Uiso 1 1 calc R . .
C8 C 0.26539(18) -0.06079(14) 0.26047(13) 0.0351(4) Uani 1 1 d . . .
H8 H 0.2829 -0.0403 0.1870 0.042 Uiso 1 1 calc R . .
C9 C 0.20982(19) -0.17072(15) 0.30710(13) 0.0387(4) Uani 1 1 d . . .
C10 C 0.14607(18) -0.20812(14) 0.24540(13) 0.0374(4) Uani 1 1 d . . .
C11 C 0.1919(2) -0.19121(19) 0.14371(15) 0.0563(6) Uani 1 1 d . . .
H11 H 0.2607 -0.1483 0.1095 0.068 Uiso 1 1 calc R . .
C12 C 0.1371(3) -0.2370(2) 0.09282(17) 0.0688(7) Uani 1 1 d . . .
H12 H 0.1714 -0.2272 0.0250 0.083 Uiso 1 1 calc R . .
C13 C 0.0311(2) -0.29758(18) 0.14146(16) 0.0538(5) Uani 1 1 d . . .
C14 C -0.1221(4) -0.4036(3) 0.1288(2) 0.1082(12) Uani 1 1 d . . .
H14A H -0.0897 -0.4702 0.1801 0.162 Uiso 1 1 calc R . .
H14B H -0.1477 -0.4238 0.0786 0.162 Uiso 1 1 calc R . .
H14C H -0.2023 -0.3596 0.1580 0.162 Uiso 1 1 calc R . .
C15 C -0.0200(2) -0.31111(18) 0.24060(16) 0.0569(6) Uani 1 1 d . . .
H15 H -0.0935 -0.3494 0.2734 0.068 Uiso 1 1 calc R . .
C16 C 0.0385(2) -0.26739(17) 0.29153(15) 0.0524(5) Uani 1 1 d . . .
H16 H 0.0043 -0.2781 0.3595 0.063 Uiso 1 1 calc R . .
C17 C 0.2853(2) 0.27439(17) 0.52494(15) 0.0533(5) Uani 1 1 d . . .
H17 H 0.2870 0.2012 0.5292 0.064 Uiso 1 1 calc R . .
C18 C 0.3761(3) 0.2956(2) 0.57070(17) 0.0625(6) Uani 1 1 d . . .
H18 H 0.4397 0.2368 0.6045 0.075 Uiso 1 1 calc R . .
C19 C 0.3735(3) 0.4025(2) 0.56678(18) 0.0645(6) Uani 1 1 d . . .
H19 H 0.4341 0.4163 0.5988 0.077 Uiso 1 1 calc R . .
C20 C 0.2816(3) 0.4892(2) 0.5157(2) 0.0647(6) Uani 1 1 d . . .
H20 H 0.2795 0.5621 0.5127 0.078 Uiso 1 1 calc R . .
C21 C 0.1922(2) 0.46817(17) 0.46860(16) 0.0514(5) Uani 1 1 d . . .
H21 H 0.1308 0.5277 0.4332 0.062 Uiso 1 1 calc R . .
C22 C 0.19161(19) 0.36075(15) 0.47274(13) 0.0390(4) Uani 1 1 d . . .
C23 C 0.0890(2) 0.33788(17) 0.42476(14) 0.0449(5) Uani 1 1 d . . .
H23A H 0.0161 0.3056 0.4770 0.054 Uiso 1 1 calc R . .
H23B H 0.0448 0.4082 0.3817 0.054 Uiso 1 1 calc R . .
C24 C 0.15747(19) 0.15023(15) 0.40234(13) 0.0381(4) Uani 1 1 d . . .
C25 C 0.23880(18) 0.09999(14) 0.31913(12) 0.0342(4) Uani 1 1 d . . .
C26 C 0.27857(18) 0.20118(14) 0.23422(12) 0.0344(4) Uani 1 1 d . . .
C27 C 0.35335(19) 0.21333(15) 0.13855(13) 0.0391(4) Uani 1 1 d . . .
H27 H 0.3892 0.1520 0.1154 0.047 Uiso 1 1 calc R . .
C28 C 0.3736(2) 0.31991(16) 0.07770(14) 0.0446(5) Uani 1 1 d . . .
C29 C 0.3206(2) 0.41257(17) 0.10964(15) 0.0514(5) Uani 1 1 d . . .
H29 H 0.3355 0.4829 0.0669 0.062 Uiso 1 1 calc R . .
C30 C 0.2450(2) 0.40047(16) 0.20569(15) 0.0476(5) Uani 1 1 d . . .
H30 H 0.2083 0.4620 0.2285 0.057 Uiso 1 1 calc R . .
C31 C 0.22596(18) 0.29490(15) 0.26638(13) 0.0369(4) Uani 1 1 d . . .
C32 C 0.15323(18) 0.03099(14) 0.29500(13) 0.0342(4) Uani 1 1 d . . .
H32 H 0.0936 -0.0049 0.3570 0.041 Uiso 1 1 calc R . .
C33 C 0.06097(19) 0.10221(15) 0.21638(13) 0.0390(4) Uani 1 1 d . . .
C34 C -0.06477(18) 0.18258(15) 0.24288(13) 0.0367(4) Uani 1 1 d . . .
C35 C -0.1338(2) 0.17122(17) 0.34052(14) 0.0450(5) Uani 1 1 d . . .
H35 H -0.0980 0.1138 0.3937 0.054 Uiso 1 1 calc R . .
C36 C -0.2565(2) 0.24565(18) 0.35894(15) 0.0508(5) Uani 1 1 d . . .
H36 H -0.3019 0.2378 0.4247 0.061 Uiso 1 1 calc R . .
C37 C -0.3122(2) 0.33130(17) 0.28094(15) 0.0480(5) Uani 1 1 d . . .
C38 C -0.4471(3) 0.4098(2) 0.3006(2) 0.0761(7) Uani 1 1 d . . .
H38A H -0.5239 0.3834 0.2933 0.114 Uiso 1 1 calc R . .
H38B H -0.4428 0.4832 0.2534 0.114 Uiso 1 1 calc R . .
H38C H -0.4607 0.4130 0.3676 0.114 Uiso 1 1 calc R . .
C39 C -0.2412(2) 0.34210(17) 0.18411(15) 0.0506(5) Uani 1 1 d . . .
H39 H -0.2768 0.3996 0.1309 0.061 Uiso 1 1 calc R . .
C40 C -0.1195(2) 0.26982(16) 0.16486(14) 0.0454(5) Uani 1 1 d . . .
H40 H -0.0732 0.2792 0.0991 0.055 Uiso 1 1 calc R . .
Cl1 Cl 0.47216(7) 0.33688(5) -0.04212(4) 0.0705(2) Uani 1 1 d . . .
N1 N 0.39242(15) -0.06676(12) 0.29633(11) 0.0373(3) Uani 1 1 d . . .
N2 N 0.15427(16) 0.26258(12) 0.36575(11) 0.0402(4) Uani 1 1 d . . .
O1 O 0.21178(17) -0.22184(12) 0.39539(10) 0.0593(4) Uani 1 1 d . . .
O2 O -0.0140(2) -0.34063(16) 0.08399(12) 0.0842(6) Uani 1 1 d . . .
O3 O 0.10813(15) 0.09825(11) 0.48656(9) 0.0499(3) Uani 1 1 d . . .
O4 O 0.09141(16) 0.09403(13) 0.13245(10) 0.0617(4) Uani 1 1 d . . .
S1 S 0.52439(6) 0.04450(5) 0.35550(4) 0.05594(17) 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
C1 C2 1.378(3) . ?
C1 C6 1.394(3) . ?
C1 N1 1.399(2) . ?
C2 C3 1.390(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.758(2) . ?
C7 N1 1.461(2) . ?
C7 C25 1.554(3) . ?
C7 S1 1.8168(19) . ?
C7 H7 0.9800 . ?
C8 N1 1.461(2) . ?
C8 C9 1.534(2) . ?
C8 C32 1.549(2) . ?
C8 H8 0.9800 . ?
C9 O1 1.213(2) . ?
C9 C10 1.480(2) . ?
C10 C16 1.382(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.362(2) . ?
C13 C15 1.362(3) . ?
C14 O2 1.414(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 C22 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.509(3) . ?
C23 N2 1.453(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O3 1.215(2) . ?
C24 N2 1.362(2) . ?
C24 C25 1.532(2) . ?
C25 C26 1.510(2) . ?
C25 C32 1.559(2) . ?
C26 C27 1.378(2) . ?
C26 C31 1.392(2) . ?
C27 C28 1.389(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(3) . ?
C28 Cl1 1.7400(19) . ?
C29 C30 1.385(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9300 . ?
C31 N2 1.406(2) . ?
C32 C33 1.525(2) . ?
C32 H32 0.9800 . ?
C33 O4 1.213(2) . ?
C33 C34 1.483(3) . ?
C34 C35 1.385(2) . ?
C34 C40 1.389(3) . ?
C35 C36 1.389(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.384(3) . ?
C36 H36 0.9300 . ?
C37 C39 1.382(3) . ?
C37 C38 1.503(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.371(3) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?

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
C2 C1 C6 119.83(18) . . ?
C2 C1 N1 125.98(17) . . ?
C6 C1 N1 114.16(17) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 S1 127.50(17) . . ?
C1 C6 S1 111.90(15) . . ?
N1 C7 C25 105.15(13) . . ?
N1 C7 S1 107.16(12) . . ?
C25 C7 S1 118.03(12) . . ?
N1 C7 H7 108.7 . . ?
C25 C7 H7 108.7 . . ?
S1 C7 H7 108.7 . . ?
N1 C8 C9 112.26(14) . . ?
N1 C8 C32 106.08(13) . . ?
C9 C8 C32 107.86(14) . . ?
N1 C8 H8 110.2 . . ?
C9 C8 H8 110.2 . . ?
C32 C8 H8 110.2 . . ?
O1 C9 C10 121.33(16) . . ?
O1 C9 C8 119.22(16) . . ?
C10 C9 C8 119.32(15) . . ?
C16 C10 C11 117.35(17) . . ?
C16 C10 C9 118.98(16) . . ?
C11 C10 C9 123.61(16) . . ?
C12 C11 C10 120.68(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O2 C13 C15 124.68(19) . . ?
O2 C13 C12 115.57(19) . . ?
C15 C13 C12 119.75(19) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 119.15(18) . . ?
C13 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C10 122.41(19) . . ?
C15 C16 H16 118.8 . . ?
C10 C16 H16 118.8 . . ?
C18 C17 C22 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C22 C17 H17 119.6 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 121.5(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C17 117.79(18) . . ?
C21 C22 C23 121.15(17) . . ?
C17 C22 C23 121.03(17) . . ?
N2 C23 C22 113.09(15) . . ?
N2 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
N2 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
O3 C24 N2 126.41(16) . . ?
O3 C24 C25 125.82(16) . . ?
N2 C24 C25 107.74(14) . . ?
C26 C25 C24 102.68(13) . . ?
C26 C25 C7 116.88(14) . . ?
C24 C25 C7 109.28(14) . . ?
C26 C25 C32 115.89(13) . . ?
C24 C25 C32 112.58(14) . . ?
C7 C25 C32 99.83(13) . . ?
C27 C26 C31 119.47(16) . . ?
C27 C26 C25 132.17(16) . . ?
C31 C26 C25 108.35(14) . . ?
C26 C27 C28 118.07(16) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 H27 121.0 . . ?
C29 C28 C27 122.26(17) . . ?
C29 C28 Cl1 118.78(15) . . ?
C27 C28 Cl1 118.95(15) . . ?
C28 C29 C30 119.71(18) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 118.13(18) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C30 C31 C26 122.36(17) . . ?
C30 C31 N2 128.15(16) . . ?
C26 C31 N2 109.50(15) . . ?
C33 C32 C8 112.52(14) . . ?
C33 C32 C25 113.00(14) . . ?
C8 C32 C25 104.62(13) . . ?
C33 C32 H32 108.8 . . ?
C8 C32 H32 108.8 . . ?
C25 C32 H32 108.8 . . ?
O4 C33 C34 120.38(17) . . ?
O4 C33 C32 120.12(17) . . ?
C34 C33 C32 119.49(15) . . ?
C35 C34 C40 118.91(17) . . ?
C35 C34 C33 123.22(16) . . ?
C40 C34 C33 117.78(16) . . ?
C34 C35 C36 119.95(18) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 121.05(18) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C39 C37 C36 118.23(18) . . ?
C39 C37 C38 120.7(2) . . ?
C36 C37 C38 121.06(19) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C37 121.37(19) . . ?
C40 C39 H39 119.3 . . ?
C37 C39 H39 119.3 . . ?
C39 C40 C34 120.49(18) . . ?
C39 C40 H40 119.8 . . ?
C34 C40 H40 119.8 . . ?
C1 N1 C8 119.78(14) . . ?
C1 N1 C7 112.46(14) . . ?
C8 N1 C7 109.33(13) . . ?
C24 N2 C31 111.73(14) . . ?
C24 N2 C23 123.39(15) . . ?
C31 N2 C23 124.84(15) . . ?
C13 O2 C14 118.7(2) . . ?
C6 S1 C7 90.86(9) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_4d
_audit_block_doi                 10.5517/cc1jbssf
_database_code_depnum_ccdc_archive 'CCDC 1410555'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 Cl2 N2 O4 S, C H2 Cl2'
_chemical_formula_sum            'C35 H28 Cl4 N2 O4 S'
_chemical_formula_weight         714.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6152(19)
_cell_length_b                   12.5567(19)
_cell_length_c                   15.206(2)
_cell_angle_alpha                70.076(4)
_cell_angle_beta                 71.090(5)
_cell_angle_gamma                65.406(5)
_cell_volume                     1692.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6154
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25399
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.56
_reflns_number_total             7748
_reflns_number_gt                3763
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0909P)²+0.9750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7748
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1815
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2204
_refine_ls_wR_factor_gt          0.1723
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3045(6) 1.2905(5) 0.1233(4) 0.0764(16) Uani 1 1 d . . .
H1 H -0.3850 1.2707 0.1580 0.092 Uiso 1 1 calc R . .
C2 C -0.3163(9) 1.3956(6) 0.0510(6) 0.107(3) Uani 1 1 d . . .
H2 H -0.4050 1.4463 0.0382 0.128 Uiso 1 1 calc R . .
C3 C -0.1988(12) 1.4254(6) -0.0018(6) 0.118(3) Uani 1 1 d . . .
H3 H -0.2076 1.4958 -0.0501 0.141 Uiso 1 1 calc R . .
C4 C -0.0698(8) 1.3517(5) 0.0169(4) 0.101(2) Uani 1 1 d . . .
H4 H 0.0105 1.3713 -0.0187 0.122 Uiso 1 1 calc R . .
C5 C -0.0575(6) 1.2469(4) 0.0893(3) 0.0739(14) Uani 1 1 d . . .
H5 H 0.0316 1.1964 0.1015 0.089 Uiso 1 1 calc R . .
C6 C -0.1750(5) 1.2162(4) 0.1436(3) 0.0534(11) Uani 1 1 d . . .
C7 C -0.1665(4) 1.1044(4) 0.2250(3) 0.0581(12) Uani 1 1 d . . .
H7A H -0.2347 1.1276 0.2816 0.070 Uiso 1 1 calc R . .
H7B H -0.1933 1.0499 0.2083 0.070 Uiso 1 1 calc R . .
C8 C 0.0116(4) 1.0640(3) 0.3144(2) 0.0400(9) Uani 1 1 d . . .
C9 C 0.1670(4) 0.9874(3) 0.3137(2) 0.0348(8) Uani 1 1 d . . .
C10 C 0.2029(4) 0.9162(3) 0.2416(2) 0.0352(8) Uani 1 1 d . . .
C11 C 0.0842(4) 0.9531(3) 0.2040(2) 0.0397(9) Uani 1 1 d . . .
C12 C 0.0839(5) 0.9063(4) 0.1347(3) 0.0497(10) Uani 1 1 d . . .
H12 H 0.0036 0.9323 0.1101 0.060 Uiso 1 1 calc R . .
C13 C 0.2074(5) 0.8192(4) 0.1027(3) 0.0547(11) Uani 1 1 d . . .
H13 H 0.2106 0.7853 0.0561 0.066 Uiso 1 1 calc R . .
C14 C 0.3248(5) 0.7825(4) 0.1389(3) 0.0501(11) Uani 1 1 d . . .
C15 C 0.3249(4) 0.8295(3) 0.2097(3) 0.0415(9) Uani 1 1 d . . .
H15 H 0.4051 0.8028 0.2345 0.050 Uiso 1 1 calc R . .
C16 C 0.1955(4) 0.9127(3) 0.4143(2) 0.0334(8) Uani 1 1 d . . .
H16 H 0.1377 0.9633 0.4599 0.040 Uiso 1 1 calc R . .
C17 C 0.1599(4) 0.8001(4) 0.4485(2) 0.0398(9) Uani 1 1 d . . .
C18 C -0.0289(6) 0.7262(5) 0.4805(4) 0.0857(17) Uani 1 1 d . . .
H18A H 0.0493 0.6500 0.4869 0.103 Uiso 1 1 calc R . .
H18B H -0.0926 0.7284 0.5427 0.103 Uiso 1 1 calc R . .
C19 C -0.1018(7) 0.7341(6) 0.4142(5) 0.110(2) Uani 1 1 d . . .
H19A H -0.1782 0.8100 0.4071 0.165 Uiso 1 1 calc R . .
H19B H -0.1392 0.6695 0.4372 0.165 Uiso 1 1 calc R . .
H19C H -0.0375 0.7280 0.3535 0.165 Uiso 1 1 calc R . .
C20 C 0.2566(4) 1.0685(3) 0.2908(2) 0.0397(9) Uani 1 1 d . . .
H20 H 0.2045 1.1308 0.3271 0.048 Uiso 1 1 calc R . .
C21 C 0.4840(4) 1.0314(4) 0.1614(3) 0.0476(10) Uani 1 1 d . . .
C22 C 0.5910(6) 1.0102(5) 0.0820(3) 0.0655(13) Uani 1 1 d . . .
H22 H 0.5778 1.0576 0.0213 0.079 Uiso 1 1 calc R . .
C23 C 0.7179(6) 0.9181(5) 0.0933(4) 0.0779(15) Uani 1 1 d . . .
H23 H 0.7899 0.9031 0.0397 0.093 Uiso 1 1 calc R . .
C24 C 0.7395(5) 0.8480(5) 0.1825(4) 0.0701(13) Uani 1 1 d . . .
H24 H 0.8260 0.7866 0.1890 0.084 Uiso 1 1 calc R . .
C25 C 0.6322(5) 0.8690(4) 0.2629(3) 0.0559(11) Uani 1 1 d . . .
H25 H 0.6465 0.8219 0.3234 0.067 Uiso 1 1 calc R . .
C26 C 0.5039(4) 0.9604(4) 0.2523(3) 0.0420(9) Uani 1 1 d . . .
C27 C 0.3522(4) 0.8907(3) 0.4061(2) 0.0355(8) Uani 1 1 d . . .
H27 H 0.4117 0.8127 0.3905 0.043 Uiso 1 1 calc R . .
C28 C 0.3792(4) 0.8950(3) 0.4975(2) 0.0361(8) Uani 1 1 d . . .
C29 C 0.4770(4) 0.7882(3) 0.5522(2) 0.0391(9) Uani 1 1 d . . .
C30 C 0.5175(5) 0.6721(4) 0.5433(3) 0.0566(11) Uani 1 1 d . . .
H30 H 0.4839 0.6582 0.5003 0.068 Uiso 1 1 calc R . .
C31 C 0.6070(5) 0.5763(4) 0.5971(4) 0.0677(13) Uani 1 1 d . . .
H31 H 0.6333 0.4984 0.5907 0.081 Uiso 1 1 calc R . .
C32 C 0.6567(5) 0.5968(4) 0.6599(3) 0.0614(12) Uani 1 1 d . . .
C33 C 0.6198(5) 0.7108(4) 0.6699(3) 0.0591(12) Uani 1 1 d . . .
H33 H 0.6550 0.7237 0.7124 0.071 Uiso 1 1 calc R . .
C34 C 0.5297(4) 0.8064(4) 0.6162(3) 0.0478(10) Uani 1 1 d . . .
H34 H 0.5041 0.8841 0.6231 0.057 Uiso 1 1 calc R . .
C35 C 0.7977(7) 0.4303(6) 0.2805(5) 0.109(2) Uani 1 1 d . . .
H35A H 0.7669 0.4272 0.2282 0.130 Uiso 1 1 calc R . .
H35B H 0.7930 0.3593 0.3316 0.130 Uiso 1 1 calc R . .
Cl1 Cl 0.48159(15) 0.67689(13) 0.09512(11) 0.0874(5) Uani 1 1 d . . .
Cl2 Cl 0.76826(19) 0.47697(14) 0.72807(13) 0.1125(6) Uani 1 1 d . . .
Cl3 Cl 0.6841(3) 0.55395(19) 0.3204(3) 0.2017(13) Uani 1 1 d . . .
Cl4 Cl 0.9732(3) 0.4242(3) 0.2412(2) 0.1845(12) Uani 1 1 d . . .
N1 N -0.0284(3) 1.0409(3) 0.2480(2) 0.0424(8) Uani 1 1 d . . .
N2 N 0.3852(3) 0.9887(3) 0.3268(2) 0.0372(7) Uani 1 1 d . . .
O1 O -0.0633(3) 1.1366(2) 0.36278(18) 0.0526(7) Uani 1 1 d . . .
O2 O 0.2406(3) 0.7010(3) 0.4717(2) 0.0625(8) Uani 1 1 d . . .
O3 O 0.0254(3) 0.8254(2) 0.4491(2) 0.0574(8) Uani 1 1 d . . .
O4 O 0.3207(3) 0.9884(2) 0.52316(19) 0.0536(7) Uani 1 1 d . . .
S1 S 0.31311(12) 1.14079(10) 0.16595(7) 0.0541(3) 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
C1 C6 1.366(6) . ?
C1 C2 1.389(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(6) . ?
C7 N1 1.441(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.216(4) . ?
C8 N1 1.366(5) . ?
C8 C9 1.524(5) . ?
C9 C10 1.505(5) . ?
C9 C16 1.548(5) . ?
C9 C20 1.552(5) . ?
C10 C15 1.370(5) . ?
C10 C11 1.389(5) . ?
C11 C12 1.372(5) . ?
C11 N1 1.407(5) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(5) . ?
C14 Cl1 1.737(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.493(5) . ?
C16 C27 1.538(5) . ?
C16 H16 0.9800 . ?
C17 O2 1.190(4) . ?
C17 O3 1.325(5) . ?
C18 C19 1.413(7) . ?
C18 O3 1.458(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.462(5) . ?
C20 S1 1.825(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.378(6) . ?
C21 C26 1.395(5) . ?
C21 S1 1.758(4) . ?
C22 C23 1.378(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(6) . ?
C25 H25 0.9300 . ?
C26 N2 1.405(5) . ?
C27 N2 1.471(4) . ?
C27 C28 1.530(5) . ?
C27 H27 0.9800 . ?
C28 O4 1.209(4) . ?
C28 C29 1.487(5) . ?
C29 C30 1.381(5) . ?
C29 C34 1.387(5) . ?
C30 C31 1.379(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.365(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.366(6) . ?
C32 Cl2 1.730(4) . ?
C33 C34 1.380(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 Cl3 1.686(7) . ?
C35 Cl4 1.739(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 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
C6 C1 C2 120.1(6) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.6(7) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.9(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.4(5) . . ?
C1 C6 C7 118.8(5) . . ?
C5 C6 C7 122.7(4) . . ?
N1 C7 C6 114.2(4) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 125.4(4) . . ?
O1 C8 C9 126.5(3) . . ?
N1 C8 C9 108.1(3) . . ?
C10 C9 C8 102.8(3) . . ?
C10 C9 C16 115.9(3) . . ?
C8 C9 C16 113.4(3) . . ?
C10 C9 C20 115.7(3) . . ?
C8 C9 C20 110.6(3) . . ?
C16 C9 C20 98.7(3) . . ?
C15 C10 C11 119.8(3) . . ?
C15 C10 C9 132.0(3) . . ?
C11 C10 C9 108.2(3) . . ?
C12 C11 C10 122.4(4) . . ?
C12 C11 N1 127.7(4) . . ?
C10 C11 N1 109.9(3) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.8(4) . . ?
C13 C14 Cl1 120.3(3) . . ?
C15 C14 Cl1 117.8(3) . . ?
C10 C15 C14 117.8(4) . . ?
C10 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C17 C16 C27 113.9(3) . . ?
C17 C16 C9 113.9(3) . . ?
C27 C16 C9 104.4(3) . . ?
C17 C16 H16 108.1 . . ?
C27 C16 H16 108.1 . . ?
C9 C16 H16 108.1 . . ?
O2 C17 O3 124.3(4) . . ?
O2 C17 C16 125.1(4) . . ?
O3 C17 C16 110.6(3) . . ?
C19 C18 O3 110.8(4) . . ?
C19 C18 H18A 109.5 . . ?
O3 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C9 105.2(3) . . ?
N2 C20 S1 107.0(2) . . ?
C9 C20 S1 118.5(2) . . ?
N2 C20 H20 108.6 . . ?
C9 C20 H20 108.6 . . ?
S1 C20 H20 108.6 . . ?
C22 C21 C26 120.3(4) . . ?
C22 C21 S1 128.2(4) . . ?
C26 C21 S1 111.5(3) . . ?
C21 C22 C23 119.4(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.0(5) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.6(4) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C21 119.8(4) . . ?
C25 C26 N2 125.5(3) . . ?
C21 C26 N2 114.7(4) . . ?
N2 C27 C28 109.4(3) . . ?
N2 C27 C16 105.5(3) . . ?
C28 C27 C16 112.4(3) . . ?
N2 C27 H27 109.9 . . ?
C28 C27 H27 109.9 . . ?
C16 C27 H27 109.9 . . ?
O4 C28 C29 120.8(3) . . ?
O4 C28 C27 118.2(3) . . ?
C29 C28 C27 121.0(3) . . ?
C30 C29 C34 118.3(4) . . ?
C30 C29 C28 123.6(3) . . ?
C34 C29 C28 118.1(3) . . ?
C31 C30 C29 121.0(4) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 119.4(4) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C33 121.1(4) . . ?
C31 C32 Cl2 119.7(4) . . ?
C33 C32 Cl2 119.3(4) . . ?
C32 C33 C34 119.4(4) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C29 120.8(4) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?
Cl3 C35 Cl4 114.5(4) . . ?
Cl3 C35 H35A 108.6 . . ?
Cl4 C35 H35A 108.6 . . ?
Cl3 C35 H35B 108.6 . . ?
Cl4 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
C8 N1 C11 110.9(3) . . ?
C8 N1 C7 122.9(3) . . ?
C11 N1 C7 126.2(3) . . ?
C26 N2 C20 112.1(3) . . ?
C26 N2 C27 119.3(3) . . ?
C20 N2 C27 108.7(3) . . ?
C17 O3 C18 118.5(3) . . ?
C21 S1 C20 90.94(18) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_4e
_audit_block_doi                 10.5517/cc1jbstg
_database_code_depnum_ccdc_archive 'CCDC 1410556'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 Cl F N2 O4 S, C H2 Cl2'
_chemical_formula_sum            'C35 H28 Cl3 F N2 O4 S'
_chemical_formula_weight         698.00

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8287(12)
_cell_length_b                   12.2767(12)
_cell_length_c                   14.9417(16)
_cell_angle_alpha                70.307(3)
_cell_angle_beta                 71.694(3)
_cell_angle_gamma                64.943(3)
_cell_volume                     1659.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8813
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24800
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.52
_reflns_number_total             7510
_reflns_number_gt                4921
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0871P)²+0.6827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7510
_refine_ls_number_parameters     426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1586
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0647(3) 0.7606(3) 0.0806(2) 0.0609(8) Uani 1 1 d . . .
H1 H 0.0224 0.7029 0.0904 0.073 Uiso 1 1 calc R . .
C2 C -0.0733(5) 0.8686(4) 0.0091(3) 0.0881(11) Uani 1 1 d . . .
H2 H 0.0074 0.8830 -0.0284 0.106 Uiso 1 1 calc R . .
C3 C -0.1996(7) 0.9534(4) -0.0064(4) 0.1037(15) Uani 1 1 d . . .
H3 H -0.2058 1.0256 -0.0550 0.124 Uiso 1 1 calc R . .
C4 C -0.3183(6) 0.9324(4) 0.0497(4) 0.1015(16) Uani 1 1 d . . .
H4 H -0.4050 0.9913 0.0400 0.122 Uiso 1 1 calc R . .
C5 C -0.3095(4) 0.8231(3) 0.1213(3) 0.0767(10) Uani 1 1 d . . .
H5 H -0.3905 0.8088 0.1581 0.092 Uiso 1 1 calc R . .
C6 C -0.1825(3) 0.7364(3) 0.13790(19) 0.0503(7) Uani 1 1 d . . .
C7 C -0.1765(3) 0.6196(3) 0.21759(19) 0.0539(7) Uani 1 1 d . . .
H7A H -0.2438 0.6417 0.2752 0.065 Uiso 1 1 calc R . .
H7B H -0.2029 0.5669 0.1971 0.065 Uiso 1 1 calc R . .
C8 C 0.0000(2) 0.5726(2) 0.31026(16) 0.0382(5) Uani 1 1 d . . .
C9 C 0.1533(2) 0.4933(2) 0.30931(15) 0.0333(5) Uani 1 1 d . . .
C10 C 0.1868(2) 0.4211(2) 0.23569(15) 0.0343(5) Uani 1 1 d . . .
C11 C 0.3054(3) 0.3297(2) 0.20461(17) 0.0425(6) Uani 1 1 d . . .
H11 H 0.3855 0.3019 0.2289 0.051 Uiso 1 1 calc R . .
C12 C 0.3005(3) 0.2804(2) 0.13531(19) 0.0506(7) Uani 1 1 d . . .
C13 C 0.1855(3) 0.3181(3) 0.0980(2) 0.0567(7) Uani 1 1 d . . .
H13 H 0.1876 0.2823 0.0515 0.068 Uiso 1 1 calc R . .
C14 C 0.0660(3) 0.4095(3) 0.12927(18) 0.0508(7) Uani 1 1 d . . .
H14 H -0.0136 0.4366 0.1046 0.061 Uiso 1 1 calc R . .
C15 C 0.0681(3) 0.4596(2) 0.19831(15) 0.0384(5) Uani 1 1 d . . .
C16 C 0.1860(2) 0.4158(2) 0.41067(15) 0.0328(5) Uani 1 1 d . . .
H16 H 0.1290 0.4669 0.4575 0.039 Uiso 1 1 calc R . .
C17 C 0.1542(3) 0.2986(2) 0.44493(16) 0.0375(5) Uani 1 1 d . . .
C18 C -0.0269(4) 0.2208(3) 0.4754(3) 0.0781(10) Uani 1 1 d . . .
H18A H 0.0514 0.1431 0.4790 0.094 Uiso 1 1 calc R . .
H18B H -0.0862 0.2204 0.5394 0.094 Uiso 1 1 calc R . .
C19 C -0.1047(5) 0.2330(4) 0.4068(3) 0.0973(13) Uani 1 1 d . . .
H19A H -0.1802 0.3112 0.4016 0.146 Uiso 1 1 calc R . .
H19B H -0.1409 0.1673 0.4291 0.146 Uiso 1 1 calc R . .
H19C H -0.0442 0.2285 0.3444 0.146 Uiso 1 1 calc R . .
C20 C 0.2394(3) 0.5775(2) 0.28649(16) 0.0379(5) Uani 1 1 d . . .
H20 H 0.1878 0.6409 0.3240 0.045 Uiso 1 1 calc R . .
C21 C 0.4612(3) 0.5459(3) 0.15640(18) 0.0485(6) Uani 1 1 d . . .
C22 C 0.5664(4) 0.5316(3) 0.0757(2) 0.0654(9) Uani 1 1 d . . .
H22 H 0.5516 0.5823 0.0149 0.078 Uiso 1 1 calc R . .
C23 C 0.6944(4) 0.4406(4) 0.0867(3) 0.0775(10) Uani 1 1 d . . .
H23 H 0.7661 0.4294 0.0327 0.093 Uiso 1 1 calc R . .
C24 C 0.7168(3) 0.3667(3) 0.1764(3) 0.0699(9) Uani 1 1 d . . .
H24 H 0.8038 0.3059 0.1824 0.084 Uiso 1 1 calc R . .
C25 C 0.6120(3) 0.3807(3) 0.2584(2) 0.0531(7) Uani 1 1 d . . .
H25 H 0.6281 0.3306 0.3192 0.064 Uiso 1 1 calc R . .
C26 C 0.4838(3) 0.4703(2) 0.24801(17) 0.0413(6) Uani 1 1 d . . .
C27 C 0.3394(2) 0.3945(2) 0.40250(15) 0.0334(5) Uani 1 1 d . . .
H27 H 0.3999 0.3145 0.3870 0.040 Uiso 1 1 calc R . .
C28 C 0.3650(2) 0.4022(2) 0.49540(16) 0.0349(5) Uani 1 1 d . . .
C29 C 0.4672(2) 0.2963(2) 0.54938(16) 0.0371(5) Uani 1 1 d . . .
C30 C 0.5130(3) 0.1760(2) 0.5401(2) 0.0538(7) Uani 1 1 d . . .
H30 H 0.4816 0.1593 0.4967 0.065 Uiso 1 1 calc R . .
C31 C 0.6051(3) 0.0804(3) 0.5949(2) 0.0663(8) Uani 1 1 d . . .
H31 H 0.6342 -0.0005 0.5895 0.080 Uiso 1 1 calc R . .
C32 C 0.6528(3) 0.1063(3) 0.6575(2) 0.0585(7) Uani 1 1 d . . .
C33 C 0.6107(3) 0.2251(3) 0.6670(2) 0.0542(7) Uani 1 1 d . . .
H33 H 0.6446 0.2414 0.7092 0.065 Uiso 1 1 calc R . .
C34 C 0.5176(3) 0.3196(2) 0.61332(18) 0.0447(6) Uani 1 1 d . . .
H34 H 0.4880 0.4001 0.6199 0.054 Uiso 1 1 calc R . .
C35 C 0.7888(5) 0.9422(4) 0.2840(4) 0.1092(14) Uani 1 1 d . . .
H35A H 0.7911 0.8870 0.2493 0.131 Uiso 0.46(3) 1 calc PR A 1
H35B H 0.7713 0.9030 0.3526 0.131 Uiso 0.46(3) 1 calc PR A 1
H35C H 0.7684 0.9361 0.2275 0.131 Uiso 0.54(3) 1 calc PR A 2
H35D H 0.7869 0.8681 0.3345 0.131 Uiso 0.54(3) 1 calc PR A 2
Cl1 Cl 0.76737(13) -0.01235(10) 0.72653(9) 0.1093(4) Uani 1 1 d . . .
Cl2 Cl 0.9514(2) 0.9483(2) 0.25491(16) 0.1934(9) Uani 1 1 d . A .
Cl3 Cl 0.6554(14) 1.0673(12) 0.2644(18) 0.206(5) Uani 0.46(3) 1 d P A 1
Cl3' Cl 0.6677(15) 1.0630(11) 0.3214(15) 0.191(6) Uani 0.54(3) 1 d P A 2
F1 F 0.4180(2) 0.19166(17) 0.10275(14) 0.0781(6) Uani 1 1 d . . .
N1 N -0.0400(2) 0.55058(19) 0.24217(14) 0.0422(5) Uani 1 1 d . . .
N2 N 0.3671(2) 0.49623(17) 0.32252(13) 0.0368(4) Uani 1 1 d . . .
O1 O -0.07198(18) 0.64539(16) 0.36058(12) 0.0497(5) Uani 1 1 d . . .
O2 O 0.2366(2) 0.19749(16) 0.46889(15) 0.0571(5) Uani 1 1 d . . .
O3 O 0.02293(19) 0.32344(17) 0.44454(13) 0.0540(5) Uani 1 1 d . . .
O4 O 0.3034(2) 0.49725(16) 0.52146(13) 0.0517(5) Uani 1 1 d . . .
S1 S 0.29005(8) 0.65319(7) 0.16092(5) 0.0533(2) 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
C1 C6 1.382(4) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(4) . ?
C7 N1 1.452(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.211(3) . ?
C8 N1 1.363(3) . ?
C8 C9 1.526(3) . ?
C9 C10 1.504(3) . ?
C9 C16 1.551(3) . ?
C9 C20 1.559(3) . ?
C10 C11 1.371(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 F1 1.355(3) . ?
C12 C13 1.360(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.397(3) . ?
C16 C17 1.504(3) . ?
C16 C27 1.540(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.195(3) . ?
C17 O3 1.323(3) . ?
C18 C19 1.453(5) . ?
C18 O3 1.456(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.461(3) . ?
C20 S1 1.815(2) . ?
C20 H20 0.9800 . ?
C21 C22 1.376(4) . ?
C21 C26 1.399(4) . ?
C21 S1 1.757(3) . ?
C22 C23 1.379(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(4) . ?
C25 H25 0.9300 . ?
C26 N2 1.397(3) . ?
C27 N2 1.471(3) . ?
C27 C28 1.537(3) . ?
C27 H27 0.9800 . ?
C28 O4 1.201(3) . ?
C28 C29 1.483(3) . ?
C29 C30 1.386(4) . ?
C29 C34 1.391(3) . ?
C30 C31 1.384(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(4) . ?
C32 Cl1 1.728(3) . ?
C33 C34 1.377(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 Cl3 1.617(12) . ?
C35 Cl3' 1.638(8) . ?
C35 Cl2 1.705(5) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
C35 H35D 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
C6 C1 C2 121.7(3) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 122.9(2) . . ?
N1 C7 C6 113.3(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 126.1(2) . . ?
O1 C8 C9 125.8(2) . . ?
N1 C8 C9 108.10(19) . . ?
C10 C9 C8 102.55(18) . . ?
C10 C9 C16 115.97(18) . . ?
C8 C9 C16 114.28(17) . . ?
C10 C9 C20 116.21(18) . . ?
C8 C9 C20 110.02(18) . . ?
C16 C9 C20 98.28(17) . . ?
C11 C10 C15 120.0(2) . . ?
C11 C10 C9 131.9(2) . . ?
C15 C10 C9 108.2(2) . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
F1 C12 C13 119.1(2) . . ?
F1 C12 C11 117.5(3) . . ?
C13 C12 C11 123.4(2) . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 117.9(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 128.3(2) . . ?
C10 C15 N1 109.79(19) . . ?
C17 C16 C27 113.91(19) . . ?
C17 C16 C9 113.78(18) . . ?
C27 C16 C9 105.19(17) . . ?
C17 C16 H16 107.9 . . ?
C27 C16 H16 107.9 . . ?
C9 C16 H16 107.9 . . ?
O2 C17 O3 125.1(2) . . ?
O2 C17 C16 124.4(2) . . ?
O3 C17 C16 110.5(2) . . ?
C19 C18 O3 109.9(3) . . ?
C19 C18 H18A 109.7 . . ?
O3 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
O3 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C9 105.23(17) . . ?
N2 C20 S1 107.31(15) . . ?
C9 C20 S1 118.50(15) . . ?
N2 C20 H20 108.5 . . ?
C9 C20 H20 108.5 . . ?
S1 C20 H20 108.5 . . ?
C22 C21 C26 120.6(3) . . ?
C22 C21 S1 127.3(2) . . ?
C26 C21 S1 112.08(19) . . ?
C21 C22 C23 118.8(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 121.1(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C25 C26 N2 126.0(2) . . ?
C25 C26 C21 120.2(2) . . ?
N2 C26 C21 113.8(2) . . ?
N2 C27 C28 108.77(17) . . ?
N2 C27 C16 104.89(17) . . ?
C28 C27 C16 112.07(17) . . ?
N2 C27 H27 110.3 . . ?
C28 C27 H27 110.3 . . ?
C16 C27 H27 110.3 . . ?
O4 C28 C29 120.9(2) . . ?
O4 C28 C27 118.3(2) . . ?
C29 C28 C27 120.76(19) . . ?
C30 C29 C34 118.8(2) . . ?
C30 C29 C28 123.3(2) . . ?
C34 C29 C28 117.9(2) . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C32 C31 C30 119.2(3) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C33 121.4(3) . . ?
C31 C32 Cl1 119.6(2) . . ?
C33 C32 Cl1 119.0(2) . . ?
C32 C33 C34 119.1(2) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C33 C34 C29 120.9(2) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?
Cl3 C35 Cl3' 31.5(4) . . ?
Cl3 C35 Cl2 120.5(5) . . ?
Cl3' C35 Cl2 113.0(5) . . ?
Cl3 C35 H35A 107.2 . . ?
Cl3' C35 H35A 134.0 . . ?
Cl2 C35 H35A 107.2 . . ?
Cl3 C35 H35B 107.2 . . ?
Cl3' C35 H35B 82.0 . . ?
Cl2 C35 H35B 107.2 . . ?
H35A C35 H35B 106.8 . . ?
Cl3 C35 H35C 78.0 . . ?
Cl3' C35 H35C 109.0 . . ?
Cl2 C35 H35C 109.0 . . ?
H35A C35 H35C 34.1 . . ?
H35B C35 H35C 133.5 . . ?
Cl3 C35 H35D 125.3 . . ?
Cl3' C35 H35D 109.0 . . ?
Cl2 C35 H35D 109.0 . . ?
H35A C35 H35D 76.7 . . ?
H35B C35 H35D 31.3 . . ?
H35C C35 H35D 107.8 . . ?
C8 N1 C15 111.27(19) . . ?
C8 N1 C7 122.5(2) . . ?
C15 N1 C7 126.2(2) . . ?
C26 N2 C20 112.83(18) . . ?
C26 N2 C27 119.77(19) . . ?
C20 N2 C27 109.29(17) . . ?
C17 O3 C18 118.4(2) . . ?
C21 S1 C20 90.90(11) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_5b
_audit_block_doi                 10.5517/cc1jbsvh
_database_code_depnum_ccdc_archive 'CCDC 1410557'
_audit_update_record             
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H26 Cl2 N2 O3 S'
_chemical_formula_sum            'C35 H26 Cl2 N2 O3 S'
_chemical_formula_weight         625.54

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1987(13)
_cell_length_b                   12.6875(15)
_cell_length_c                   13.8047(18)
_cell_angle_alpha                102.851(4)
_cell_angle_beta                 96.021(4)
_cell_angle_gamma                101.520(4)
_cell_volume                     1685.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7011
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25368
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7698
_reflns_number_gt                3921
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0932P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7698
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8700(3) 0.3405(3) 0.7161(2) 0.0842(9) Uani 1 1 d . . .
H1 H 0.8816 0.3875 0.6731 0.101 Uiso 1 1 calc R . .
C2 C 0.9791(4) 0.3353(5) 0.7801(3) 0.1271(16) Uani 1 1 d . . .
H2 H 1.0639 0.3800 0.7817 0.153 Uiso 1 1 calc R . .
C3 C 0.9637(6) 0.2655(5) 0.8407(4) 0.1428(19) Uani 1 1 d . . .
H3 H 1.0384 0.2615 0.8833 0.171 Uiso 1 1 calc R . .
C4 C 0.8388(6) 0.2002(4) 0.8403(3) 0.1299(17) Uani 1 1 d . . .
H4 H 0.8287 0.1512 0.8816 0.156 Uiso 1 1 calc R . .
C5 C 0.7286(4) 0.2083(3) 0.7779(2) 0.0915(10) Uani 1 1 d . . .
H5 H 0.6429 0.1664 0.7788 0.110 Uiso 1 1 calc R . .
C6 C 0.7440(3) 0.2774(2) 0.71457(19) 0.0596(7) Uani 1 1 d . . .
C7 C 0.6243(3) 0.2872(2) 0.64733(19) 0.0636(7) Uani 1 1 d . . .
H7A H 0.5467 0.2293 0.6484 0.076 Uiso 1 1 calc R . .
H7B H 0.6029 0.3583 0.6731 0.076 Uiso 1 1 calc R . .
C8 C 0.6548(2) 0.3629(2) 0.49821(19) 0.0515(6) Uani 1 1 d . . .
C9 C 0.6768(2) 0.32097(17) 0.39057(17) 0.0474(6) Uani 1 1 d . . .
C10 C 0.6816(2) 0.20145(17) 0.38557(17) 0.0451(6) Uani 1 1 d . . .
C11 C 0.6951(2) 0.11711(19) 0.3085(2) 0.0567(6) Uani 1 1 d . . .
H11 H 0.7059 0.1288 0.2453 0.068 Uiso 1 1 calc R . .
C12 C 0.6922(3) 0.0127(2) 0.3277(2) 0.0637(7) Uani 1 1 d . . .
C13 C 0.6747(2) -0.0056(2) 0.4205(2) 0.0620(7) Uani 1 1 d . . .
H13 H 0.6730 -0.0756 0.4313 0.074 Uiso 1 1 calc R . .
C14 C 0.6596(2) 0.0786(2) 0.4976(2) 0.0537(6) Uani 1 1 d . . .
H14 H 0.6476 0.0668 0.5605 0.064 Uiso 1 1 calc R . .
C15 C 0.6629(2) 0.18167(18) 0.47815(18) 0.0438(5) Uani 1 1 d . . .
C16 C 0.5711(2) 0.34094(18) 0.31055(17) 0.0461(6) Uani 1 1 d . . .
H16 H 0.5373 0.4051 0.3424 0.055 Uiso 1 1 calc R . .
C17 C 0.4500(2) 0.2421(2) 0.2718(2) 0.0529(6) Uani 1 1 d . . .
C18 C 0.3489(2) 0.21889(18) 0.33841(18) 0.0474(6) Uani 1 1 d . . .
C19 C 0.3426(2) 0.29495(19) 0.4252(2) 0.0540(6) Uani 1 1 d . . .
H19 H 0.4047 0.3632 0.4438 0.065 Uiso 1 1 calc R . .
C20 C 0.2456(2) 0.2718(2) 0.4856(2) 0.0602(7) Uani 1 1 d . . .
H20 H 0.2456 0.3235 0.5450 0.072 Uiso 1 1 calc R . .
C21 C 0.1497(3) 0.1734(2) 0.4584(2) 0.0643(7) Uani 1 1 d . . .
C22 C 0.0420(3) 0.1509(3) 0.5231(3) 0.0973(10) Uani 1 1 d . . .
H22A H -0.0355 0.0972 0.4830 0.146 Uiso 1 1 calc R . .
H22B H 0.0158 0.2187 0.5507 0.146 Uiso 1 1 calc R . .
H22C H 0.0772 0.1227 0.5769 0.146 Uiso 1 1 calc R . .
C23 C 0.1557(3) 0.0965(2) 0.3701(2) 0.0723(8) Uani 1 1 d . . .
H23 H 0.0919 0.0291 0.3506 0.087 Uiso 1 1 calc R . .
C24 C 0.2529(3) 0.1180(2) 0.3121(2) 0.0643(7) Uani 1 1 d . . .
H24 H 0.2553 0.0648 0.2542 0.077 Uiso 1 1 calc R . .
C25 C 0.8071(2) 0.4013(2) 0.3738(2) 0.0584(7) Uani 1 1 d . . .
H25 H 0.8070 0.4777 0.4083 0.070 Uiso 1 1 calc R . .
C26 C 0.9695(3) 0.3063(3) 0.2892(3) 0.0949(11) Uani 1 1 d . . .
H26 H 1.0306 0.2629 0.2706 0.114 Uiso 1 1 calc R . .
C27 C 0.8742(3) 0.3211(3) 0.2232(3) 0.0826(9) Uani 1 1 d . . .
H27 H 0.8617 0.2877 0.1547 0.099 Uiso 1 1 calc R . .
C28 C 0.6481(2) 0.37208(19) 0.22823(18) 0.0520(6) Uani 1 1 d . . .
H28 H 0.6224 0.3121 0.1664 0.062 Uiso 1 1 calc R . .
C29 C 0.6261(2) 0.4825(2) 0.20740(19) 0.0541(6) Uani 1 1 d . . .
C30 C 0.6608(2) 0.51191(19) 0.11339(18) 0.0506(6) Uani 1 1 d . . .
C31 C 0.7151(3) 0.4460(2) 0.0420(2) 0.0691(7) Uani 1 1 d . . .
H31 H 0.7301 0.3789 0.0518 0.083 Uiso 1 1 calc R . .
C32 C 0.7475(3) 0.4775(3) -0.0433(2) 0.0768(8) Uani 1 1 d . . .
H32 H 0.7856 0.4329 -0.0900 0.092 Uiso 1 1 calc R . .
C33 C 0.7232(3) 0.5750(3) -0.0585(2) 0.0725(8) Uani 1 1 d . . .
C34 C 0.6674(3) 0.6426(2) 0.0107(2) 0.0748(8) Uani 1 1 d . . .
H34 H 0.6506 0.7087 -0.0002 0.090 Uiso 1 1 calc R . .
C35 C 0.6373(3) 0.6102(2) 0.0959(2) 0.0610(7) Uani 1 1 d . . .
H35 H 0.6003 0.6554 0.1429 0.073 Uiso 1 1 calc R . .
Cl1 Cl 0.71513(11) -0.09506(7) 0.23374(7) 0.1136(4) Uani 1 1 d . . .
Cl2 Cl 0.75962(12) 0.61319(10) -0.16701(7) 0.1268(4) Uani 1 1 d . . .
N1 N 0.64801(19) 0.27791(16) 0.54405(15) 0.0517(5) Uani 1 1 d . . .
N2 N 0.7936(2) 0.39194(17) 0.26645(17) 0.0622(6) Uani 1 1 d . . .
O1 O 0.64615(18) 0.45683(14) 0.53724(14) 0.0701(5) Uani 1 1 d . . .
O2 O 0.4379(2) 0.18338(17) 0.18739(16) 0.0825(6) Uani 1 1 d . . .
O3 O 0.5879(2) 0.54737(16) 0.26957(16) 0.0917(7) Uani 1 1 d . . .
S1 S 0.96968(7) 0.37411(6) 0.41114(7) 0.0816(3) 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
C1 C6 1.367(4) . ?
C1 C2 1.369(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(4) . ?
C7 N1 1.454(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.218(3) . ?
C8 N1 1.360(3) . ?
C8 C9 1.519(3) . ?
C9 C10 1.513(3) . ?
C9 C16 1.559(3) . ?
C9 C25 1.576(3) . ?
C10 C11 1.371(3) . ?
C10 C15 1.381(3) . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C12 Cl1 1.734(3) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.397(3) . ?
C16 C28 1.525(3) . ?
C16 C17 1.526(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.214(3) . ?
C17 C18 1.481(3) . ?
C18 C19 1.378(3) . ?
C18 C24 1.395(3) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.397(4) . ?
C21 C22 1.510(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.450(3) . ?
C25 S1 1.807(2) . ?
C25 H25 0.9800 . ?
C26 C27 1.331(4) . ?
C26 S1 1.712(4) . ?
C26 H26 0.9300 . ?
C27 N2 1.415(3) . ?
C27 H27 0.9300 . ?
C28 N2 1.474(3) . ?
C28 C29 1.544(3) . ?
C28 H28 0.9800 . ?
C29 O3 1.204(3) . ?
C29 C30 1.486(3) . ?
C30 C31 1.382(3) . ?
C30 C35 1.383(3) . ?
C31 C32 1.376(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.365(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.384(4) . ?
C33 Cl2 1.728(3) . ?
C34 C35 1.373(4) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?

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
C6 C1 C2 120.7(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 120.7(2) . . ?
N1 C7 C6 112.6(2) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 125.8(2) . . ?
O1 C8 C9 125.9(2) . . ?
N1 C8 C9 108.28(19) . . ?
C10 C9 C8 102.39(18) . . ?
C10 C9 C16 116.70(18) . . ?
C8 C9 C16 113.61(18) . . ?
C10 C9 C25 118.13(18) . . ?
C8 C9 C25 107.44(18) . . ?
C16 C9 C25 98.78(17) . . ?
C11 C10 C15 120.0(2) . . ?
C11 C10 C9 131.9(2) . . ?
C15 C10 C9 108.03(19) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 Cl1 119.1(2) . . ?
C11 C12 Cl1 119.6(2) . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C10 C15 C14 122.3(2) . . ?
C10 C15 N1 110.21(19) . . ?
C14 C15 N1 127.5(2) . . ?
C28 C16 C17 113.7(2) . . ?
C28 C16 C9 106.56(18) . . ?
C17 C16 C9 112.66(17) . . ?
C28 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
C9 C16 H16 107.9 . . ?
O2 C17 C18 120.9(2) . . ?
O2 C17 C16 119.9(2) . . ?
C18 C17 C16 119.2(2) . . ?
C19 C18 C24 117.8(2) . . ?
C19 C18 C17 122.5(2) . . ?
C24 C18 C17 119.7(2) . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C23 117.9(2) . . ?
C20 C21 C22 120.1(3) . . ?
C23 C21 C22 122.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C21 C23 H23 119.3 . . ?
C23 C24 C18 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C18 C24 H24 119.6 . . ?
N2 C25 C9 106.03(19) . . ?
N2 C25 S1 106.77(17) . . ?
C9 C25 S1 117.60(16) . . ?
N2 C25 H25 108.7 . . ?
C9 C25 H25 108.7 . . ?
S1 C25 H25 108.7 . . ?
C27 C26 S1 114.1(2) . . ?
C27 C26 H26 122.9 . . ?
S1 C26 H26 122.9 . . ?
C26 C27 N2 114.1(3) . . ?
C26 C27 H27 122.9 . . ?
N2 C27 H27 122.9 . . ?
N2 C28 C16 107.04(19) . . ?
N2 C28 C29 105.95(18) . . ?
C16 C28 C29 111.91(19) . . ?
N2 C28 H28 110.6 . . ?
C16 C28 H28 110.6 . . ?
C29 C28 H28 110.6 . . ?
O3 C29 C30 119.9(2) . . ?
O3 C29 C28 120.1(2) . . ?
C30 C29 C28 119.9(2) . . ?
C31 C30 C35 118.0(2) . . ?
C31 C30 C29 123.5(2) . . ?
C35 C30 C29 118.5(2) . . ?
C32 C31 C30 121.4(2) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C33 C32 C31 119.2(3) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 121.0(3) . . ?
C32 C33 Cl2 119.4(2) . . ?
C34 C33 Cl2 119.6(2) . . ?
C35 C34 C33 118.8(3) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C30 121.5(3) . . ?
C34 C35 H35 119.2 . . ?
C30 C35 H35 119.2 . . ?
C8 N1 C15 111.08(19) . . ?
C8 N1 C7 123.6(2) . . ?
C15 N1 C7 125.3(2) . . ?
C27 N2 C25 109.4(2) . . ?
C27 N2 C28 121.5(2) . . ?
C25 N2 C28 107.40(18) . . ?
C26 S1 C25 89.52(14) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.047



loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.032 0.000 0.000 243 48 ' '
_platon_squeeze_details          
; 
;

#=====================================================================
