# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# 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_20150108_art1_0m
_database_code_depnum_ccdc_archive 'CCDC 1435601'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 O4 S2'
_chemical_formula_sum            'C34 H32 N2 O4 S2'
_chemical_formula_weight         596.74

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.442(4)
_cell_length_b                   15.052(3)
_cell_length_c                   8.5086(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.057(2)
_cell_angle_gamma                90.00
_cell_volume                     2976.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    5504
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.27

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          .4022
_exptl_crystal_size_mid          .2510
_exptl_crystal_size_min          .2100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15556
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         26.35
_reflns_number_total             3030
_reflns_number_gt                2355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v.  5.4.5'

_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)+(0.0504P)²+3.2560P] 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         3030
_refine_ls_number_parameters     240
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.34502(7) 1.03833(11) 0.1740(2) 0.0489(5) Uani 1 1 d . . .
O2 O 0.30243(8) 0.76633(11) 0.3494(3) 0.0611(6) Uani 1 1 d . . .
N1 N 0.33615(8) 0.89303(13) 0.2542(3) 0.0466(5) Uani 1 1 d . . .
S1 S 0.07421(2) 1.04628(4) 0.43082(7) 0.03241(17) Uani 1 1 d . . .
C6 C 0.18004(9) 1.04976(14) 0.3031(3) 0.0325(5) Uani 1 1 d . . .
H6 H 0.1553 1.0988 0.2996 0.039 Uiso 1 1 calc R . .
C5 C 0.16509(9) 0.96658(14) 0.3514(2) 0.0283(5) Uani 1 1 d . . .
C4 C 0.11209(9) 0.95520(14) 0.3949(2) 0.0290(5) Uani 1 1 d . . .
C3 C 0.08592(9) 0.87838(15) 0.4186(3) 0.0353(5) Uani 1 1 d . . .
H3 H 0.1001 0.8210 0.4053 0.042 Uiso 1 1 calc R . .
C1 C 0.02359(9) 0.97998(15) 0.4776(3) 0.0319(5) Uani 1 1 d . . .
C10 C 0.20196(9) 0.89359(14) 0.3587(3) 0.0302(5) Uani 1 1 d . A .
H10 H 0.1932 0.8366 0.3925 0.036 Uiso 1 1 calc R . .
C7 C 0.22993(9) 1.06303(14) 0.2600(3) 0.0338(5) Uani 1 1 d . . .
H7 H 0.2396 1.1199 0.2280 0.041 Uiso 1 1 calc R . .
C9 C 0.25109(9) 0.90761(14) 0.3150(3) 0.0315(5) Uani 1 1 d . . .
C11 C 0.29753(10) 0.84479(15) 0.3118(3) 0.0426(6) Uani 1 1 d . A .
C8 C 0.26481(9) 0.99033(14) 0.2656(3) 0.0317(5) Uani 1 1 d . A .
C12 C 0.31916(10) 0.98226(15) 0.2241(3) 0.0384(5) Uani 1 1 d . A .
C2 C 0.03594(10) 0.89226(15) 0.4648(3) 0.0369(5) Uani 1 1 d . . .
H2 H 0.0131 0.8452 0.4850 0.044 Uiso 1 1 calc R . .
C13 C 0.3803(3) 0.8629(4) 0.1847(7) 0.0312(16) Uani 0.455(5) 1 d PD A 1
H13 H 0.3990 0.9159 0.1521 0.037 Uiso 0.455(5) 1 calc PR A 1
C14 C 0.3579(3) 0.8003(6) 0.0325(10) 0.0435(19) Uani 0.455(5) 1 d PD A 1
H14A H 0.3472 0.7424 0.0694 0.052 Uiso 0.455(5) 1 calc PR A 1
H14B H 0.3229 0.8265 -0.0462 0.052 Uiso 0.455(5) 1 calc PR A 1
C15 C 0.4229(3) 0.8177(4) 0.3269(7) 0.0493(17) Uani 0.455(5) 1 d PD A 1
H15A H 0.4545 0.7935 0.2898 0.059 Uiso 0.455(5) 1 calc PR A 1
H15B H 0.4039 0.7671 0.3631 0.059 Uiso 0.455(5) 1 calc PR A 1
C16 C 0.4483(4) 0.8798(8) 0.4739(8) 0.067(3) Uani 0.455(5) 1 d PD A 1
H16A H 0.4436 0.9416 0.4358 0.100 Uiso 0.455(5) 1 calc PR A 1
H16B H 0.4894 0.8668 0.5238 0.100 Uiso 0.455(5) 1 calc PR A 1
H16C H 0.4283 0.8708 0.5562 0.100 Uiso 0.455(5) 1 calc PR A 1
C17 C 0.4026(3) 0.7856(4) -0.0549(7) 0.0560(18) Uani 0.455(5) 1 d PD A 1
H17A H 0.4365 0.7567 0.0208 0.084 Uiso 0.455(5) 1 calc PR A 1
H17B H 0.4138 0.8429 -0.0902 0.084 Uiso 0.455(5) 1 calc PR A 1
H17C H 0.3864 0.7477 -0.1518 0.084 Uiso 0.455(5) 1 calc PR A 1
C13B C 0.3928(3) 0.8467(4) 0.2512(7) 0.052(2) Uani 0.545(5) 1 d PD A 2
H13B H 0.3931 0.7847 0.2937 0.062 Uiso 0.545(5) 1 calc PR A 2
C14B C 0.3879(3) 0.8420(4) 0.0661(7) 0.0587(16) Uani 0.545(5) 1 d PD A 2
H14C H 0.3821 0.9028 0.0194 0.070 Uiso 0.545(5) 1 calc PR A 2
H14D H 0.4246 0.8193 0.0553 0.070 Uiso 0.545(5) 1 calc PR A 2
C15B C 0.4461(2) 0.8943(4) 0.3578(8) 0.0566(16) Uani 0.545(5) 1 d PD A 2
H15C H 0.4806 0.8691 0.3369 0.068 Uiso 0.545(5) 1 calc PR A 2
H15D H 0.4438 0.9580 0.3278 0.068 Uiso 0.545(5) 1 calc PR A 2
C16B C 0.4519(4) 0.8850(7) 0.5390(8) 0.0560(19) Uani 0.545(5) 1 d PD A 2
H16D H 0.4177 0.9099 0.5597 0.084 Uiso 0.545(5) 1 calc PR A 2
H16E H 0.4862 0.9170 0.6052 0.084 Uiso 0.545(5) 1 calc PR A 2
H16F H 0.4555 0.8220 0.5696 0.084 Uiso 0.545(5) 1 calc PR A 2
C17B C 0.3399(3) 0.7843(5) -0.0322(9) 0.061(2) Uani 0.545(5) 1 d PD A 2
H17D H 0.3040 0.8028 -0.0138 0.091 Uiso 0.545(5) 1 calc PR A 2
H17E H 0.3482 0.7223 0.0024 0.091 Uiso 0.545(5) 1 calc PR A 2
H17F H 0.3361 0.7898 -0.1499 0.091 Uiso 0.545(5) 1 calc PR A 2


_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
O1 C12 1.209(3) . ?
O2 C11 1.219(3) . ?
N1 C11 1.395(3) . ?
N1 C12 1.406(3) . ?
N1 C13 1.455(7) . ?
N1 C13B 1.558(7) . ?
S1 C1 1.729(2) . ?
S1 C4 1.734(2) . ?
C6 C7 1.392(3) . ?
C6 C5 1.401(3) . ?
C6 H6 0.9500 . ?
C5 C10 1.410(3) . ?
C5 C4 1.463(3) . ?
C4 C3 1.366(3) . ?
C3 C2 1.410(3) . ?
C3 H3 0.9500 . ?
C1 C2 1.366(3) . ?
C1 C1 1.452(4) 5_576 ?
C10 C9 1.379(3) . ?
C10 H10 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C9 C8 1.388(3) . ?
C9 C11 1.484(3) . ?
C8 C12 1.481(3) . ?
C2 H2 0.9500 . ?
C13 C15 1.494(7) . ?
C13 C14 1.557(7) . ?
C13 H13 1.0000 . ?
C14 C17 1.516(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.531(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13B C15B 1.517(7) . ?
C13B C14B 1.544(6) . ?
C13B H13B 1.0000 . ?
C14B C17B 1.490(7) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.510(6) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?

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
C11 N1 C12 111.56(18) . . ?
C11 N1 C13 130.5(3) . . ?
C12 N1 C13 116.0(3) . . ?
C11 N1 C13B 118.3(3) . . ?
C12 N1 C13B 129.7(3) . . ?
C13 N1 C13B 22.8(2) . . ?
C1 S1 C4 92.50(10) . . ?
C7 C6 C5 122.34(19) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C5 C10 119.19(19) . . ?
C6 C5 C4 120.70(18) . . ?
C10 C5 C4 120.11(19) . . ?
C3 C4 C5 128.90(19) . . ?
C3 C4 S1 110.06(16) . . ?
C5 C4 S1 121.01(16) . . ?
C4 C3 C2 113.7(2) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C2 C1 C1 129.4(3) . 5_576 ?
C2 C1 S1 110.34(16) . . ?
C1 C1 S1 120.2(2) 5_576 . ?
C9 C10 C5 117.85(19) . . ?
C9 C10 H10 121.1 . . ?
C5 C10 H10 121.1 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C10 C9 C8 122.09(19) . . ?
C10 C9 C11 130.0(2) . . ?
C8 C9 C11 107.94(18) . . ?
O2 C11 N1 125.0(2) . . ?
O2 C11 C9 128.7(2) . . ?
N1 C11 C9 106.23(19) . . ?
C7 C8 C9 121.15(19) . . ?
C7 C8 C12 130.3(2) . . ?
C9 C8 C12 108.50(19) . . ?
O1 C12 N1 125.0(2) . . ?
O1 C12 C8 129.2(2) . . ?
N1 C12 C8 105.74(19) . . ?
C1 C2 C3 113.4(2) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
N1 C13 C15 103.4(4) . . ?
N1 C13 C14 114.3(5) . . ?
C15 C13 C14 112.0(6) . . ?
N1 C13 H13 109.0 . . ?
C15 C13 H13 109.0 . . ?
C14 C13 H13 109.0 . . ?
C17 C14 C13 112.0(5) . . ?
C17 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C17 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C13 C15 C16 112.8(6) . . ?
C13 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C13 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15B C13B C14B 114.4(6) . . ?
C15B C13B N1 112.4(5) . . ?
C14B C13B N1 104.4(4) . . ?
C15B C13B H13B 108.5 . . ?
C14B C13B H13B 108.5 . . ?
N1 C13B H13B 108.5 . . ?
C17B C14B C13B 113.5(5) . . ?
C17B C14B H14C 108.9 . . ?
C13B C14B H14C 108.9 . . ?
C17B C14B H14D 108.9 . . ?
C13B C14B H14D 108.9 . . ?
H14C C14B H14D 107.7 . . ?
C16B C15B C13B 111.0(5) . . ?
C16B C15B H15C 109.4 . . ?
C13B C15B H15C 109.4 . . ?
C16B C15B H15D 109.4 . . ?
C13B C15B H15D 109.4 . . ?
H15C C15B H15D 108.0 . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047

_publ_section_expl_refinement    
;
The H atoms were placed in geometrically idealized positions 
with C-H 
distances of 0.93Å (aromatic),0.97Å 
(idealized CH₂) and 0.96Å
(idealized CH₃) and were
 constrained to ride on the parent C atom 
with Uiso(H) 
= 1.2Ueq(C) for the aromatic, CH₂ and C-H protons and 
Uiso(H) 
= 1.5Ueq(C) for the idealized CH₃ protons. 


;
####################################################################### 
# 
# 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_20150424_art5_0ma
_database_code_depnum_ccdc_archive 'CCDC 1435602'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 O4 S2'
_chemical_formula_sum            'C34 H32 N2 O4 S2'
_chemical_formula_weight         596.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   5.271(7)
_cell_length_b                   9.681(13)
_cell_length_c                   28.26(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.742(16)
_cell_angle_gamma                90
_cell_volume                     1437(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    1219
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      20.09

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4827
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15891
_diffrn_reflns_av_unetI/netI     0.2580
_diffrn_reflns_av_R_equivalents  0.2901
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         27.209
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.007
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.007
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.007
_reflns_number_total             3220
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v.  5.4.5'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1366P)²+10.0256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3220
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2543
_refine_ls_R_factor_gt           0.1412
_refine_ls_wR_factor_ref         0.3692
_refine_ls_wR_factor_gt          0.3028
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.1926(6) 1.4125(3) 0.04701(10) 0.0319(8) Uani 1 1 d . . . . .
O1 O 0.6603(16) 0.9020(9) 0.1828(3) 0.043(2) Uani 1 1 d . . . . .
O2 O -0.0721(18) 0.7114(8) 0.1115(3) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.312(2) 0.7746(9) 0.1536(3) 0.034(2) Uani 1 1 d . . . . .
C1 C -0.438(2) 1.4326(9) 0.0036(4) 0.030(3) Uani 1 1 d . . . . .
C2 C -0.494(2) 1.3085(11) -0.0190(4) 0.033(3) Uani 1 1 d . . . . .
H2 H -0.6208 1.2986 -0.0447 0.040 Uiso 1 1 calc R U . . .
C3 C -0.345(2) 1.1995(11) -0.0005(4) 0.031(3) Uani 1 1 d . . . . .
H3 H -0.3680 1.1070 -0.0112 0.037 Uiso 1 1 calc R U . . .
C4 C -0.163(2) 1.2374(10) 0.0347(4) 0.027(3) Uani 1 1 d . . . . .
C5 C 0.013(2) 1.1517(11) 0.0642(4) 0.028(3) Uani 1 1 d . . . . .
C6 C 0.237(2) 1.2077(10) 0.0857(4) 0.029(3) Uani 1 1 d . . . . .
H6 H 0.2775 1.3010 0.0790 0.034 Uiso 1 1 calc R U . . .
C7 C 0.407(3) 1.1322(11) 0.1169(4) 0.038(3) Uani 1 1 d . . . . .
H7 H 0.5607 1.1708 0.1312 0.046 Uiso 1 1 calc R U . . .
C8 C 0.334(2) 0.9953(11) 0.1252(4) 0.031(3) Uani 1 1 d . . . . .
C9 C 0.119(2) 0.9410(10) 0.1038(4) 0.030(3) Uani 1 1 d . . . . .
C10 C -0.048(2) 1.0138(11) 0.0732(4) 0.032(3) Uani 1 1 d . . . . .
H10 H -0.1978 0.9722 0.0587 0.038 Uiso 1 1 calc R U . . .
C11 C 0.466(2) 0.8905(11) 0.1580(4) 0.029(3) Uani 1 1 d . . . . .
C12 C 0.100(3) 0.7921(11) 0.1215(4) 0.036(3) Uani 1 1 d . . . . .
C13 C 0.399(3) 0.5258(11) 0.1504(5) 0.055(4) Uani 1 1 d . . . . .
H13A H 0.5013 0.5492 0.1250 0.066 Uiso 1 1 d R U . . .
H13B H 0.4807 0.4537 0.1695 0.066 Uiso 1 1 d R U . . .
H13C H 0.2033 0.5018 0.1374 0.066 Uiso 1 1 d R U . . .
C14 C 0.364(3) 0.6463(11) 0.1813(4) 0.044(4) Uani 1 1 d . . . . .
H14 H 0.5371 0.6618 0.1978 0.053 Uiso 1 1 calc R U . . .
C15 C 0.195(3) 0.6339(13) 0.2204(5) 0.056(4) Uani 1 1 d . . . . .
H15C H 0.0626 0.6010 0.2105 0.067 Uiso 1 1 d R U . . .
H15D H 0.2979 0.5500 0.2441 0.067 Uiso 1 1 d R U . . .
C16 C 0.185(3) 0.7489(14) 0.2545(4) 0.051(4) Uani 1 1 d . . . . .
H16A H 0.1288 0.8332 0.2369 0.061 Uiso 1 1 calc R U . . .
H16B H 0.3599 0.7662 0.2690 0.061 Uiso 1 1 calc R U . . .
C17 C 0.013(3) 0.7263(15) 0.2938(5) 0.057(4) Uani 1 1 d . . . . .
H17A H -0.1648 0.7367 0.2812 0.086 Uiso 1 1 calc R U . . .
H17B H 0.0521 0.7945 0.3190 0.086 Uiso 1 1 calc R U . . .
H17C H 0.0394 0.6331 0.3068 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.718(11) . ?
S1 C4 1.740(10) . ?
O1 C11 1.198(13) . ?
O2 C12 1.211(15) . ?
N1 C11 1.386(14) . ?
N1 C12 1.391(16) . ?
N1 C14 1.481(13) . ?
C1 C2 1.381(14) . ?
C1 C1 1.467(19) 3_485 ?
C2 C3 1.389(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.455(15) . ?
C5 C6 1.396(15) . ?
C5 C10 1.400(15) . ?
C6 C7 1.408(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.346(16) . ?
C8 C11 1.506(15) . ?
C9 C10 1.374(16) . ?
C9 C12 1.532(15) . ?
C10 H10 0.9500 . ?
C13 C14 1.477(15) . ?
C13 H13A 0.9593 . ?
C13 H13B 0.9634 . ?
C13 H13C 1.0896 . ?
C14 C15 1.482(18) . ?
C14 H14 1.0000 . ?
C15 C16 1.477(17) . ?
C15 H15C 0.7969 . ?
C15 H15D 1.1583 . ?
C16 C17 1.507(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 92.4(5) . . ?
C11 N1 C12 113.2(9) . . ?
C11 N1 C14 123.3(10) . . ?
C12 N1 C14 123.5(10) . . ?
C2 C1 C1 129.4(13) . 3_485 ?
C2 C1 S1 110.5(8) . . ?
C1 C1 S1 120.0(10) 3_485 . ?
C1 C2 C3 113.2(10) . . ?
C1 C2 H2 123.4 . . ?
C3 C2 H2 123.4 . . ?
C4 C3 C2 114.1(10) . . ?
C4 C3 H3 123.0 . . ?
C2 C3 H3 123.0 . . ?
C3 C4 C5 129.6(9) . . ?
C3 C4 S1 109.6(8) . . ?
C5 C4 S1 120.3(8) . . ?
C6 C5 C10 119.3(10) . . ?
C6 C5 C4 120.4(10) . . ?
C10 C5 C4 120.3(11) . . ?
C5 C6 C7 122.9(10) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C8 C7 C6 115.0(11) . . ?
C8 C7 H7 122.5 . . ?
C6 C7 H7 122.5 . . ?
C9 C8 C7 121.8(11) . . ?
C9 C8 C11 110.1(10) . . ?
C7 C8 C11 128.1(11) . . ?
C8 C9 C10 123.5(10) . . ?
C8 C9 C12 107.2(10) . . ?
C10 C9 C12 129.3(11) . . ?
C9 C10 C5 117.4(11) . . ?
C9 C10 H10 121.3 . . ?
C5 C10 H10 121.3 . . ?
O1 C11 N1 126.5(10) . . ?
O1 C11 C8 128.9(11) . . ?
N1 C11 C8 104.6(9) . . ?
O2 C12 N1 128.2(10) . . ?
O2 C12 C9 126.8(11) . . ?
N1 C12 C9 104.9(10) . . ?
C14 C13 H13A 111.0 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 109.6 . . ?
C14 C13 H13C 102.1 . . ?
H13A C13 H13C 112.0 . . ?
H13B C13 H13C 113.7 . . ?
C13 C14 N1 112.1(9) . . ?
C13 C14 C15 119.2(11) . . ?
N1 C14 C15 111.3(10) . . ?
C13 C14 H14 104.1 . . ?
N1 C14 H14 104.1 . . ?
C15 C14 H14 104.1 . . ?
C16 C15 C14 118.9(12) . . ?
C16 C15 H15C 117.0 . . ?
C14 C15 H15C 109.5 . . ?
C16 C15 H15D 101.0 . . ?
C14 C15 H15D 101.9 . . ?
H15C C15 H15D 106.1 . . ?
C15 C16 C17 115.3(13) . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.775
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.126

_shelxl_version_number           2013-4


_publ_section_expl_refinement    
;
The H atoms were placed in geometrically idealized positions 
with C-H 
distances of 0.93Å (aromatic),0.97Å 
(idealized CH₂) and 0.96Å
(idealized CH₃) and were
 constrained to ride on the parent C atom 
with Uiso(H) 
= 1.2Ueq(C) for the aromatic, CH₂ and C-H protons and 
Uiso(H) 
= 1.5Ueq(C) for the idealized CH₃ protons. 

Initially, the structure was solved in P1 with an R1 value
 ~=0.33, however the  change of Space Group to P2(1)/c ) was 
suggested by Platon-ADDSYM. The original solution in P1 required
the use of main restraints in order to obtain an acceptable model, however
transitioning to P2(1)/c allowed for removal of the restraints from the model.
In addition, a Twin law was found and appliedto the model with a BASF 
value of 0.24. Application of the twin law and refinement in P2(1)/c 
resulted in an R factor of 0.1443.

Additionally, it should be noted that despite the lower data quality,
neither the connectivity nor the packing arrangement 
of the atoms or molecules are in question.
;

# start Validation Reply Form
_vrf_RINTA01_20150424_Art5_0ma   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Crystals of the title compound were extremely 
resistant to crystalization attempts and produced only 
small, weakly diffracting crystals.
;
_vrf_PLAT020_20150424_Art5_0ma   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.290 Report
RESPONSE:  Crystals of the title compound were extremely 
resistant to crystalization attempts and produced only 
small, weakly diffracting crystals.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_06_02_2014_ADH2nap2_0ma
_database_code_depnum_ccdc_archive 'CCDC 1435603'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H48 N2 O4 S2'
_chemical_formula_sum            'C48 H48 N2 O4 S2'
_chemical_formula_weight         781.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.870(13)
_cell_length_b                   9.773(14)
_cell_length_c                   13.13(3)
_cell_angle_alpha                94.98(2)
_cell_angle_beta                 93.06(2)
_cell_angle_gamma                116.609(15)
_cell_volume                     1008(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.3515
_shelx_estimated_absorpt_T_max   0.7457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11387
_diffrn_reflns_av_unetI/netI     0.3251
_diffrn_reflns_av_R_equivalents  0.2034
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         28.435
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4660
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v.  5.4.5'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4660
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2914
_refine_ls_R_factor_gt           0.1161
_refine_ls_wR_factor_ref         0.2638
_refine_ls_wR_factor_gt          0.2137
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.2796(2) -0.4095(2) 0.11603(15) 0.0386(6) Uani 1 1 d . . . . .
O1 O 0.5819(6) -0.1905(6) 0.3531(4) 0.0529(15) Uani 1 1 d . . . . .
O2 O 0.7937(6) 0.2427(5) 0.1928(4) 0.0447(14) Uani 1 1 d . . . . .
N1 N 0.6854(6) 0.0258(6) 0.2742(4) 0.0376(16) Uani 1 1 d . . . . .
C1 C -0.4055(8) -0.4663(7) 0.0001(5) 0.0322(18) Uani 1 1 d . . . . .
C2 C -0.3123(8) -0.4332(7) -0.0802(5) 0.0349(18) Uani 1 1 d . . . . .
H2 H -0.3599 -0.4553 -0.1498 0.042 Uiso 1 1 calc R U . . .
C3 C -0.1335(8) -0.3612(8) -0.0495(6) 0.039(2) Uani 1 1 d . . . . .
H3 H -0.0501 -0.3319 -0.0966 0.047 Uiso 1 1 calc R U . . .
C4 C -0.0961(7) -0.3393(7) 0.0536(5) 0.0303(17) Uani 1 1 d . . . . .
C5 C 0.0710(8) -0.2779(8) 0.1165(6) 0.0377(19) Uani 1 1 d . . . . .
C6 C 0.0937(8) -0.3554(8) 0.1935(6) 0.044(2) Uani 1 1 d . . . . .
H6 H 0.0005 -0.4463 0.2088 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2546(8) -0.3016(8) 0.2509(5) 0.0398(19) Uani 1 1 d . . . . .
H7 H 0.2693 -0.3594 0.3016 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3889(8) -0.1664(8) 0.2333(5) 0.0355(18) Uani 1 1 d . . . . .
C9 C 0.3694(8) -0.0782(8) 0.1587(5) 0.0330(18) Uani 1 1 d . . . . .
C10 C 0.2062(8) -0.1326(8) 0.0993(5) 0.0341(18) Uani 1 1 d . . . . .
C11 C 0.1926(8) -0.0386(8) 0.0273(5) 0.0362(18) Uani 1 1 d . . . . .
H11 H 0.0870 -0.0717 -0.0126 0.043 Uiso 1 1 calc R U . . .
C12 C 0.3248(8) 0.0977(8) 0.0128(5) 0.0357(18) Uani 1 1 d . . . . .
H12 H 0.3105 0.1571 -0.0370 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4851(8) 0.1517(8) 0.0723(5) 0.0366(18) Uani 1 1 d . . . . .
H13 H 0.5775 0.2469 0.0625 0.044 Uiso 1 1 calc R U . . .
C14 C 0.5035(8) 0.0642(8) 0.1437(5) 0.0315(17) Uani 1 1 d . . . . .
C15 C 0.6736(9) 0.1213(9) 0.2046(5) 0.0379(19) Uani 1 1 d . . . . .
C16 C 0.5592(8) -0.1142(8) 0.2923(6) 0.0376(19) Uani 1 1 d . . . . .
C17 C 0.8556(8) 0.0757(9) 0.3331(5) 0.043(2) Uani 1 1 d . . . . .
H17A H 0.8398 0.0507 0.4045 0.052 Uiso 1 1 calc R U . . .
H17B H 0.9238 0.1887 0.3359 0.052 Uiso 1 1 calc R U . . .
C18 C 0.9509(8) -0.0056(8) 0.2820(5) 0.0410(19) Uani 1 1 d . . . . .
H18A H 0.9674 0.0201 0.2108 0.049 Uiso 1 1 calc R U . . .
H18B H 0.8820 -0.1187 0.2786 0.049 Uiso 1 1 calc R U . . .
C19 C 1.1244(8) 0.0436(8) 0.3423(5) 0.0373(18) Uani 1 1 d . . . . .
H19A H 1.1103 0.0439 0.4166 0.045 Uiso 1 1 calc R U . . .
H19B H 1.1641 -0.0340 0.3226 0.045 Uiso 1 1 calc R U . . .
C20 C 1.2604(8) 0.2024(8) 0.3243(6) 0.044(2) Uani 1 1 d . . . . .
H20A H 1.2196 0.2798 0.3416 0.053 Uiso 1 1 calc R U . . .
H20B H 1.2783 0.2012 0.2505 0.053 Uiso 1 1 calc R U . . .
C21 C 1.4310(8) 0.2514(8) 0.3884(5) 0.0400(19) Uani 1 1 d . . . . .
H21A H 1.4117 0.2495 0.4620 0.048 Uiso 1 1 calc R U . . .
H21B H 1.4720 0.1745 0.3699 0.048 Uiso 1 1 calc R U . . .
C22 C 1.5668(8) 0.4079(8) 0.3748(6) 0.049(2) Uani 1 1 d . . . . .
H22A H 1.5249 0.4846 0.3919 0.059 Uiso 1 1 calc R U . . .
H22B H 1.5879 0.4091 0.3016 0.059 Uiso 1 1 calc R U . . .
C23 C 1.7355(8) 0.4579(9) 0.4405(6) 0.052(2) Uani 1 1 d . . . . .
H23A H 1.7136 0.4503 0.5135 0.062 Uiso 1 1 calc R U . . .
H23B H 1.7818 0.3855 0.4202 0.062 Uiso 1 1 calc R U . . .
C24 C 1.8690(9) 0.6223(8) 0.4309(6) 0.057(2) Uani 1 1 d . . . . .
H24A H 1.8933 0.6306 0.3591 0.085 Uiso 1 1 calc R U . . .
H24B H 1.9732 0.6460 0.4743 0.085 Uiso 1 1 calc R U . . .
H24C H 1.8261 0.6954 0.4532 0.085 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.729(7) . ?
S1 C4 1.741(7) . ?
O1 C16 1.206(7) . ?
O2 C15 1.218(8) . ?
N1 C16 1.376(8) . ?
N1 C15 1.394(8) . ?
N1 C17 1.505(8) . ?
C1 C2 1.346(9) . ?
C1 C1 1.502(12) 2_445 ?
C2 C3 1.434(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.351(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.492(9) . ?
C5 C6 1.373(9) . ?
C5 C10 1.436(9) . ?
C6 C7 1.423(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(9) . ?
C8 C16 1.503(9) . ?
C9 C14 1.407(9) . ?
C9 C10 1.451(9) . ?
C10 C11 1.411(9) . ?
C11 C12 1.362(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.431(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.505(9) . ?
C17 C18 1.538(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.539(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.529(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.497(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.535(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.532(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 91.3(3) . . ?
C16 N1 C15 127.0(6) . . ?
C16 N1 C17 115.6(6) . . ?
C15 N1 C17 117.4(6) . . ?
C2 C1 C1 128.7(7) . 2_445 ?
C2 C1 S1 111.8(5) . . ?
C1 C1 S1 119.4(6) 2_445 . ?
C1 C2 C3 112.8(6) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C4 C3 C2 112.9(6) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C5 130.2(6) . . ?
C3 C4 S1 111.2(5) . . ?
C5 C4 S1 118.5(5) . . ?
C6 C5 C10 120.0(6) . . ?
C6 C5 C4 120.6(6) . . ?
C10 C5 C4 119.4(7) . . ?
C5 C6 C7 120.9(7) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.4(7) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.7(6) . . ?
C7 C8 C16 119.6(7) . . ?
C9 C8 C16 119.7(6) . . ?
C14 C9 C8 121.2(6) . . ?
C14 C9 C10 119.5(6) . . ?
C8 C9 C10 119.3(6) . . ?
C11 C10 C5 124.6(6) . . ?
C11 C10 C9 117.0(6) . . ?
C5 C10 C9 118.4(6) . . ?
C12 C11 C10 122.6(7) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 120.2(7) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.1(6) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 121.6(6) . . ?
C13 C14 C15 118.5(6) . . ?
C9 C14 C15 119.8(6) . . ?
O2 C15 N1 122.2(6) . . ?
O2 C15 C14 121.9(7) . . ?
N1 C15 C14 115.9(6) . . ?
O1 C16 N1 122.4(7) . . ?
O1 C16 C8 121.3(6) . . ?
N1 C16 C8 116.3(7) . . ?
N1 C17 C18 110.8(5) . . ?
N1 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 111.2(6) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 114.0(6) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 113.0(6) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 114.8(6) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 114.7(6) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 113.9(6) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 0.0(6) . . . . ?
C4 S1 C1 C1 -176.4(7) . . . 2_445 ?
C1 C1 C2 C3 176.6(8) 2_445 . . . ?
S1 C1 C2 C3 0.6(8) . . . . ?
C1 C2 C3 C4 -1.0(9) . . . . ?
C2 C3 C4 C5 175.9(7) . . . . ?
C2 C3 C4 S1 1.0(8) . . . . ?
C1 S1 C4 C3 -0.6(6) . . . . ?
C1 S1 C4 C5 -176.1(6) . . . . ?
C3 C4 C5 C6 -130.7(8) . . . . ?
S1 C4 C5 C6 43.8(9) . . . . ?
C3 C4 C5 C10 52.4(10) . . . . ?
S1 C4 C5 C10 -133.0(6) . . . . ?
C10 C5 C6 C7 -6.0(10) . . . . ?
C4 C5 C6 C7 177.2(6) . . . . ?
C5 C6 C7 C8 3.1(11) . . . . ?
C6 C7 C8 C9 0.5(10) . . . . ?
C6 C7 C8 C16 -178.1(6) . . . . ?
C7 C8 C9 C14 176.7(6) . . . . ?
C16 C8 C9 C14 -4.7(10) . . . . ?
C7 C8 C9 C10 -0.9(10) . . . . ?
C16 C8 C9 C10 177.6(6) . . . . ?
C6 C5 C10 C11 -175.4(7) . . . . ?
C4 C5 C10 C11 1.5(10) . . . . ?
C6 C5 C10 C9 5.4(10) . . . . ?
C4 C5 C10 C9 -177.7(6) . . . . ?
C14 C9 C10 C11 1.1(9) . . . . ?
C8 C9 C10 C11 178.8(6) . . . . ?
C14 C9 C10 C5 -179.7(6) . . . . ?
C8 C9 C10 C5 -2.0(10) . . . . ?
C5 C10 C11 C12 -179.2(7) . . . . ?
C9 C10 C11 C12 0.0(10) . . . . ?
C10 C11 C12 C13 -0.6(10) . . . . ?
C11 C12 C13 C14 0.1(10) . . . . ?
C12 C13 C14 C9 0.9(10) . . . . ?
C12 C13 C14 C15 179.1(6) . . . . ?
C8 C9 C14 C13 -179.2(7) . . . . ?
C10 C9 C14 C13 -1.5(10) . . . . ?
C8 C9 C14 C15 2.6(10) . . . . ?
C10 C9 C14 C15 -179.7(6) . . . . ?
C16 N1 C15 O2 -178.8(7) . . . . ?
C17 N1 C15 O2 -1.8(10) . . . . ?
C16 N1 C15 C14 0.4(10) . . . . ?
C17 N1 C15 C14 177.4(6) . . . . ?
C13 C14 C15 O2 0.6(10) . . . . ?
C9 C14 C15 O2 178.8(7) . . . . ?
C13 C14 C15 N1 -178.6(6) . . . . ?
C9 C14 C15 N1 -0.3(9) . . . . ?
C15 N1 C16 O1 178.7(7) . . . . ?
C17 N1 C16 O1 1.7(10) . . . . ?
C15 N1 C16 C8 -2.4(10) . . . . ?
C17 N1 C16 C8 -179.4(6) . . . . ?
C7 C8 C16 O1 2.0(11) . . . . ?
C9 C8 C16 O1 -176.6(7) . . . . ?
C7 C8 C16 N1 -177.0(6) . . . . ?
C9 C8 C16 N1 4.5(9) . . . . ?
C16 N1 C17 C18 80.0(8) . . . . ?
C15 N1 C17 C18 -97.4(7) . . . . ?
N1 C17 C18 C19 -179.5(6) . . . . ?
C17 C18 C19 C20 -77.5(8) . . . . ?
C18 C19 C20 C21 177.9(6) . . . . ?
C19 C20 C21 C22 -178.8(6) . . . . ?
C20 C21 C22 C23 178.8(6) . . . . ?
C21 C22 C23 C24 -176.2(6) . . . . ?

_refine_diff_density_max         0.757
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4


_publ_section_expl_refinement    
;
The H atoms were placed in geometrically idealized positions 
with C-H 
distances of 0.93Å (aromatic),0.97Å 
(idealized CH₂) and 0.96Å
(idealized CH₃) and were
 constrained to ride on the parent C atom 
with Uiso(H) 
= 1.2Ueq(C) for the aromatic, CH₂ and C-H protons and 
Uiso(H) 
= 1.5Ueq(C) for the idealized CH₃ protons. 
;
####################################################################### 
# 
# 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_20150126_art3_0m
_database_code_depnum_ccdc_archive 'CCDC 1435604'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 O4 S2'
_chemical_formula_sum            'C34 H32 N2 O4 S2'
_chemical_formula_weight         596.74

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'

_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                   7.8929(13)
_cell_length_b                   13.988(2)
_cell_length_c                   14.098(2)
_cell_angle_alpha                100.290(2)
_cell_angle_beta                 99.834(2)
_cell_angle_gamma                102.275(2)
_cell_volume                     1460.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    4731
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.59

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          .3020
_exptl_crystal_size_mid          .2200
_exptl_crystal_size_min          .1981
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5851
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      125(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14222
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5162
_reflns_number_gt                3610
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v.  5.3.1'

_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)+(0.0474P)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         5162
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
S1 S 1.01882(8) 0.68145(4) 0.03321(4) 0.02917(17) Uani 1 1 d . . .
S2 S 0.68846(8) 0.44946(4) 0.14094(4) 0.02801(17) Uani 1 1 d . . .
O2 O 0.9625(2) 0.67515(12) -0.48136(12) 0.0344(4) Uani 1 1 d . . .
O4 O 0.6561(2) 0.47076(12) 0.64612(11) 0.0327(4) Uani 1 1 d . . .
O3 O 0.2645(2) 0.16986(12) 0.48906(12) 0.0354(4) Uani 1 1 d . . .
O1 O 1.3719(2) 0.97204(12) -0.33003(12) 0.0402(4) Uani 1 1 d . . .
N2 N 0.4485(2) 0.31765(13) 0.59014(13) 0.0252(4) Uani 1 1 d . . .
C8 C 0.8635(3) 0.57685(16) 0.04110(17) 0.0251(5) Uani 1 1 d . . .
C9 C 0.5753(3) 0.39853(17) 0.57997(17) 0.0261(5) Uani 1 1 d . . .
C10 C 0.9234(3) 0.53735(16) 0.29908(17) 0.0276(5) Uani 1 1 d . . .
H10 H 0.9893 0.5555 0.3654 0.033 Uiso 1 1 calc R . .
C11 C 0.5885(3) 0.37861(16) 0.47424(16) 0.0232(5) Uani 1 1 d . . .
C12 C 0.6696(3) 0.40128(16) 0.32277(17) 0.0255(5) Uani 1 1 d . . .
C13 C 1.1827(3) 0.85233(16) -0.26146(17) 0.0256(5) Uani 1 1 d . . .
C14 C 0.7693(3) 0.46205(16) 0.26601(16) 0.0253(5) Uani 1 1 d . . .
N1 N 1.1718(2) 0.82819(14) -0.42920(14) 0.0283(5) Uani 1 1 d . . .
C16 C 0.4674(3) 0.28774(16) 0.42593(17) 0.0248(5) Uani 1 1 d . . .
C17 C 0.3767(3) 0.24689(17) 0.49962(17) 0.0268(5) Uani 1 1 d . . .
C18 C 0.9331(3) 0.66531(16) -0.09244(16) 0.0257(5) Uani 1 1 d . . .
C19 C 1.2575(3) 0.89608(17) -0.33882(18) 0.0303(6) Uani 1 1 d . . .
C20 C 0.9714(3) 0.70166(16) -0.25483(16) 0.0250(5) Uani 1 1 d . . .
H20 H 0.8855 0.6410 -0.2876 0.030 Uiso 1 1 calc R . .
C21 C 0.7914(3) 0.58324(17) -0.12407(17) 0.0283(6) Uani 1 1 d . . .
H21 H 0.7255 0.5619 -0.1904 0.034 Uiso 1 1 calc R . .
C22 C 0.3811(3) 0.31102(17) 0.67960(16) 0.0290(6) Uani 1 1 d . . .
H22A H 0.2511 0.2819 0.6604 0.035 Uiso 1 1 calc R . .
H22B H 0.4019 0.3798 0.7199 0.035 Uiso 1 1 calc R . .
C23 C 1.0505(3) 0.74607(17) -0.41591(18) 0.0276(5) Uani 1 1 d . . .
C24 C 1.0572(3) 0.76293(16) -0.30754(16) 0.0250(5) Uani 1 1 d . . .
C25 C 0.8605(3) 0.54653(16) 0.13414(17) 0.0255(5) Uani 1 1 d . . .
C26 C 0.6913(3) 0.43613(16) 0.42529(16) 0.0258(5) Uani 1 1 d . . .
H26 H 0.7742 0.4974 0.4596 0.031 Uiso 1 1 calc R . .
C27 C 1.1403(3) 0.82315(16) -0.10547(17) 0.0296(6) Uani 1 1 d . . .
H27 H 1.1682 0.8438 -0.0355 0.036 Uiso 1 1 calc R . .
C28 C 1.0145(3) 0.73139(16) -0.15103(17) 0.0246(5) Uani 1 1 d . . .
C29 C 0.5470(3) 0.30945(16) 0.27474(17) 0.0275(5) Uani 1 1 d . . .
H29 H 0.5331 0.2862 0.2056 0.033 Uiso 1 1 calc R . .
C30 C 1.1232(3) 0.90496(17) -0.57629(17) 0.0285(6) Uani 1 1 d . . .
H30A H 0.9931 0.8782 -0.5875 0.034 Uiso 1 1 calc R . .
H30B H 1.1552 0.9736 -0.5341 0.034 Uiso 1 1 calc R . .
C31 C 0.9735(3) 0.58486(17) 0.22442(17) 0.0281(6) Uani 1 1 d . . .
H31 H 1.0764 0.6386 0.2358 0.034 Uiso 1 1 calc R . .
C32 C 1.1751(3) 0.90915(17) -0.67460(17) 0.0312(6) Uani 1 1 d . . .
H32A H 1.1375 0.8406 -0.7172 0.037 Uiso 1 1 calc R . .
H32B H 1.3061 0.9314 -0.6630 0.037 Uiso 1 1 calc R . .
C33 C 1.2246(3) 0.88417(17) -0.15996(18) 0.0316(6) Uani 1 1 d . . .
H33 H 1.3084 0.9460 -0.1283 0.038 Uiso 1 1 calc R . .
C34 C 0.4455(3) 0.25189(17) 0.32566(17) 0.0285(6) Uani 1 1 d . . .
H34 H 0.3637 0.1899 0.2925 0.034 Uiso 1 1 calc R . .
C35 C 1.0947(3) 0.97892(17) -0.72920(17) 0.0310(6) Uani 1 1 d . . .
H35A H 1.1284 1.0470 -0.6859 0.037 Uiso 1 1 calc R . .
H35B H 0.9636 0.9552 -0.7437 0.037 Uiso 1 1 calc R . .
C36 C 0.4635(3) 0.24888(18) 0.74308(18) 0.0330(6) Uani 1 1 d . . .
H36A H 0.5925 0.2799 0.7666 0.040 Uiso 1 1 calc R . .
H36B H 0.4478 0.1806 0.7030 0.040 Uiso 1 1 calc R . .
C37 C 0.3784(3) 0.24172(17) 0.83132(17) 0.0301(6) Uani 1 1 d . . .
H37A H 0.2501 0.2092 0.8070 0.036 Uiso 1 1 calc R . .
H37B H 0.3901 0.3104 0.8693 0.036 Uiso 1 1 calc R . .
C38 C 0.4590(3) 0.18304(19) 0.90039(18) 0.0393(7) Uani 1 1 d . . .
H38A H 0.5845 0.2189 0.9299 0.047 Uiso 1 1 calc R . .
H38B H 0.4573 0.1163 0.8616 0.047 Uiso 1 1 calc R . .
C39 C 1.2175(3) 0.83831(18) -0.52391(17) 0.0320(6) Uani 1 1 d . . .
H39A H 1.1879 0.7707 -0.5679 0.038 Uiso 1 1 calc R . .
H39B H 1.3473 0.8662 -0.5126 0.038 Uiso 1 1 calc R . .
C1 C 0.7521(3) 0.53339(17) -0.04925(17) 0.0289(6) Uani 1 1 d . . .
H1 H 0.6575 0.4752 -0.0603 0.035 Uiso 1 1 calc R . .
C2 C 1.1551(3) 0.98478(19) -0.82570(18) 0.0405(7) Uani 1 1 d . . .
H2A H 1.2849 1.0076 -0.8120 0.061 Uiso 1 1 calc R . .
H2B H 1.1028 1.0323 -0.8566 0.061 Uiso 1 1 calc R . .
H2C H 1.1163 0.9183 -0.8704 0.061 Uiso 1 1 calc R . .
C3 C 0.3600(3) 0.16886(19) 0.98320(18) 0.0411(7) Uani 1 1 d . . .
H3A H 0.3587 0.2346 1.0210 0.062 Uiso 1 1 calc R . .
H3B H 0.4202 0.1336 1.0271 0.062 Uiso 1 1 calc R . .
H3C H 0.2378 0.1293 0.9546 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.731(2) . ?
S1 C18 1.741(2) . ?
S2 C25 1.733(2) . ?
S2 C14 1.733(2) . ?
O2 C23 1.216(3) . ?
O4 C9 1.218(2) . ?
O3 C17 1.208(2) . ?
O1 C19 1.211(3) . ?
N2 C9 1.389(3) . ?
N2 C17 1.412(3) . ?
N2 C22 1.460(3) . ?
C8 C1 1.371(3) . ?
C8 C25 1.451(3) . ?
C9 C11 1.492(3) . ?
C10 C14 1.375(3) . ?
C10 C31 1.409(3) . ?
C10 H10 0.9500 . ?
C11 C26 1.376(3) . ?
C11 C16 1.395(3) . ?
C12 C29 1.408(3) . ?
C12 C26 1.409(3) . ?
C12 C14 1.468(3) . ?
C13 C33 1.380(3) . ?
C13 C24 1.389(3) . ?
C13 C19 1.489(3) . ?
N1 C23 1.393(3) . ?
N1 C19 1.408(3) . ?
N1 C39 1.464(3) . ?
C16 C34 1.381(3) . ?
C16 C17 1.487(3) . ?
C18 C21 1.367(3) . ?
C18 C28 1.467(3) . ?
C20 C24 1.378(3) . ?
C20 C28 1.408(3) . ?
C20 H20 0.9500 . ?
C21 C1 1.406(3) . ?
C21 H21 0.9500 . ?
C22 C36 1.516(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.494(3) . ?
C25 C31 1.367(3) . ?
C26 H26 0.9500 . ?
C27 C33 1.388(3) . ?
C27 C28 1.411(3) . ?
C27 H27 0.9500 . ?
C29 C34 1.390(3) . ?
C29 H29 0.9500 . ?
C30 C32 1.518(3) . ?
C30 C39 1.524(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31 0.9500 . ?
C32 C35 1.520(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C2 1.526(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.520(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.524(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C3 1.530(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C1 H1 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
C8 S1 C18 92.35(11) . . ?
C25 S2 C14 92.31(11) . . ?
C9 N2 C17 111.55(18) . . ?
C9 N2 C22 124.77(19) . . ?
C17 N2 C22 123.30(18) . . ?
C1 C8 C25 128.4(2) . . ?
C1 C8 S1 110.29(17) . . ?
C25 C8 S1 121.27(17) . . ?
O4 C9 N2 125.1(2) . . ?
O4 C9 C11 128.4(2) . . ?
N2 C9 C11 106.51(19) . . ?
C14 C10 C31 113.1(2) . . ?
C14 C10 H10 123.5 . . ?
C31 C10 H10 123.5 . . ?
C26 C11 C16 122.2(2) . . ?
C26 C11 C9 129.9(2) . . ?
C16 C11 C9 107.84(19) . . ?
C29 C12 C26 119.4(2) . . ?
C29 C12 C14 120.3(2) . . ?
C26 C12 C14 120.2(2) . . ?
C33 C13 C24 120.8(2) . . ?
C33 C13 C19 130.9(2) . . ?
C24 C13 C19 108.2(2) . . ?
C10 C14 C12 128.8(2) . . ?
C10 C14 S2 110.43(17) . . ?
C12 C14 S2 120.61(17) . . ?
C23 N1 C19 111.67(19) . . ?
C23 N1 C39 124.3(2) . . ?
C19 N1 C39 123.79(19) . . ?
C34 C16 C11 120.7(2) . . ?
C34 C16 C17 131.1(2) . . ?
C11 C16 C17 108.16(19) . . ?
O3 C17 N2 124.4(2) . . ?
O3 C17 C16 129.7(2) . . ?
N2 C17 C16 105.94(18) . . ?
C21 C18 C28 128.2(2) . . ?
C21 C18 S1 110.04(17) . . ?
C28 C18 S1 121.72(16) . . ?
O1 C19 N1 124.6(2) . . ?
O1 C19 C13 129.5(2) . . ?
N1 C19 C13 105.87(19) . . ?
C24 C20 C28 118.2(2) . . ?
C24 C20 H20 120.9 . . ?
C28 C20 H20 120.9 . . ?
C18 C21 C1 113.7(2) . . ?
C18 C21 H21 123.1 . . ?
C1 C21 H21 123.1 . . ?
N2 C22 C36 114.83(19) . . ?
N2 C22 H22A 108.6 . . ?
C36 C22 H22A 108.6 . . ?
N2 C22 H22B 108.6 . . ?
C36 C22 H22B 108.6 . . ?
H22A C22 H22B 107.5 . . ?
O2 C23 N1 125.1(2) . . ?
O2 C23 C24 128.7(2) . . ?
N1 C23 C24 106.16(19) . . ?
C20 C24 C13 122.1(2) . . ?
C20 C24 C23 129.7(2) . . ?
C13 C24 C23 108.05(19) . . ?
C31 C25 C8 130.2(2) . . ?
C31 C25 S2 110.39(17) . . ?
C8 C25 S2 119.41(17) . . ?
C11 C26 C12 117.9(2) . . ?
C11 C26 H26 121.0 . . ?
C12 C26 H26 121.0 . . ?
C33 C27 C28 121.9(2) . . ?
C33 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C20 C28 C27 119.0(2) . . ?
C20 C28 C18 119.7(2) . . ?
C27 C28 C18 121.3(2) . . ?
C34 C29 C12 121.8(2) . . ?
C34 C29 H29 119.1 . . ?
C12 C29 H29 119.1 . . ?
C32 C30 C39 110.65(19) . . ?
C32 C30 H30A 109.5 . . ?
C39 C30 H30A 109.5 . . ?
C32 C30 H30B 109.5 . . ?
C39 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C25 C31 C10 113.8(2) . . ?
C25 C31 H31 123.1 . . ?
C10 C31 H31 123.1 . . ?
C30 C32 C35 114.05(19) . . ?
C30 C32 H32A 108.7 . . ?
C35 C32 H32A 108.7 . . ?
C30 C32 H32B 108.7 . . ?
C35 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C13 C33 C27 118.0(2) . . ?
C13 C33 H33 121.0 . . ?
C27 C33 H33 121.0 . . ?
C16 C34 C29 117.9(2) . . ?
C16 C34 H34 121.0 . . ?
C29 C34 H34 121.0 . . ?
C32 C35 C2 112.8(2) . . ?
C32 C35 H35A 109.0 . . ?
C2 C35 H35A 109.0 . . ?
C32 C35 H35B 109.0 . . ?
C2 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C22 C36 C37 111.03(19) . . ?
C22 C36 H36A 109.4 . . ?
C37 C36 H36A 109.4 . . ?
C22 C36 H36B 109.4 . . ?
C37 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C36 C37 C38 113.94(19) . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37B 108.8 . . ?
C38 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C37 C38 C3 112.8(2) . . ?
C37 C38 H38A 109.0 . . ?
C3 C38 H38A 109.0 . . ?
C37 C38 H38B 109.0 . . ?
C3 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
N1 C39 C30 114.29(19) . . ?
N1 C39 H39A 108.7 . . ?
C30 C39 H39A 108.7 . . ?
N1 C39 H39B 108.7 . . ?
C30 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C8 C1 C21 113.6(2) . . ?
C8 C1 H1 123.2 . . ?
C21 C1 H1 123.2 . . ?
C35 C2 H2A 109.5 . . ?
C35 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C35 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C38 C3 H3A 109.5 . . ?
C38 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C38 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048

_publ_section_expl_refinement    
;
The H atoms were placed in geometrically idealized positions 
with C-H 
distances of 0.93Å (aromatic),0.97Å 
(idealized CH₂) and 0.96Å
(idealized CH₃) and were
 constrained to ride on the parent C atom 
with Uiso(H) 
= 1.2Ueq(C) for the aromatic, CH₂ and C-H protons and 
Uiso(H) 
= 1.5Ueq(C) for the idealized CH₃ protons. 
;
