# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1058344'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_shelx               
;
PROBLEM: Short Inter XH3 .. XHn     H15    ..  H13D    ..       1.74 Ang.  
RESPONSE: The short contact is a consequence of the molecular conformation.
;
_vrf_PLAT414_shelx               
;
PROBLEM: Short Intra D-H..H-X       H2N    ..  H4A     ..       1.84 Ang.  
RESPONSE: The short contact is a consequence of the molecular conformation.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'compound 4d and DNP adduct'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N4 O4'
_chemical_formula_sum            'C25 H24 N4 O4'
_chemical_formula_weight         444.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   20.3743(10)
_cell_length_b                   5.7348(4)
_cell_length_c                   19.2424(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.342(6)
_cell_angle_gamma                90
_cell_volume                     2196.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10380
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      76.0

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.760
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22364
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.443
_diffrn_reflns_theta_max         76.290
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4531
_reflns_number_gt                4116
_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       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
 The cyclohexylidene portion of the molecule was disordered.  The disorder 
was modeled by assigning the variable x to the site occupancy factors of 
one component of the disordered group.  The group consisted of atoms C1, 
C2, C3, C4, C5, C6 and C13.  The alternate component consisted of atoms, 
C1a, C2a, C3a, C4a, C5a, C6a and C13a.  The site occupancy for these latter 
atoms was set to (1-x).  A common isotropic displacement parameter was 
refined for all affected atoms while refining x.  In this way, the site 
occupancy for the major component (C1 through C13) refined to 88(2)%.  Hydrogen 
atoms were calculated in idealized positions for all atoms.  The non-H 
atoms of the major component were refined anisotropically with their 
displacement parameters restrained to be approximately isotropic.  The 
atoms of the minor component were refined with fixed isotropic displacement 
parameters.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+1.3994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4531
_refine_ls_number_parameters     327
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82532(9) 0.3372(3) 0.33334(9) 0.0271(4) Uani 0.88 1 d D U P A 1
H1 H 0.8064 0.2143 0.3603 0.033 Uiso 0.88 1 calc R U P A 1
C2 C 0.78841(8) 0.3223(3) 0.25510(9) 0.0284(4) Uani 0.88 1 d D U P A 1
H2A H 0.8109 0.4263 0.2264 0.034 Uiso 0.88 1 calc R U P A 1
H2B H 0.7916 0.1608 0.2379 0.034 Uiso 0.88 1 calc R U P A 1
C3 C 0.71535(8) 0.3898(3) 0.24377(9) 0.0271(4) Uani 0.88 1 d D U P A 1
C4 C 0.70253(9) 0.6187(4) 0.27668(11) 0.0334(4) Uani 0.88 1 d D U P A 1
H4A H 0.6536 0.6391 0.2728 0.040 Uiso 0.88 1 calc R U P A 1
H4B H 0.7186 0.7481 0.2506 0.040 Uiso 0.88 1 calc R U P A 1
C5 C 0.73848(10) 0.6268(4) 0.35469(12) 0.0331(7) Uani 0.88 1 d D U P A 1
H5A H 0.7178 0.5111 0.3816 0.040 Uiso 0.88 1 calc R U P A 1
H5B H 0.7322 0.7832 0.3741 0.040 Uiso 0.88 1 calc R U P A 1
C6 C 0.81385(8) 0.5761(4) 0.36574(10) 0.0274(4) Uani 0.88 1 d D U P A 1
H6 H 0.8346 0.6991 0.3406 0.033 Uiso 0.88 1 calc R U P A 1
C13 C 0.84692(9) 0.5859(4) 0.44488(10) 0.0351(4) Uani 0.88 1 d D U P A 1
H13A H 0.8371 0.7366 0.4645 0.053 Uiso 0.88 1 calc R U P A 1
H13B H 0.8956 0.5675 0.4509 0.053 Uiso 0.88 1 calc R U P A 1
H13C H 0.8292 0.4600 0.4700 0.053 Uiso 0.88 1 calc R U P A 1
C1A C 0.8296(6) 0.398(2) 0.3162(7) 0.030 Uiso 0.12 1 d D U P A 2
H1A H 0.8278 0.5211 0.2790 0.036 Uiso 0.12 1 calc R U P A 2
C2A C 0.7822(5) 0.1912(19) 0.2917(7) 0.030 Uiso 0.12 1 d D U P A 2
H2A1 H 0.7932 0.1202 0.2486 0.036 Uiso 0.12 1 calc R U P A 2
H2A2 H 0.7886 0.0712 0.3295 0.036 Uiso 0.12 1 calc R U P A 2
C3A C 0.7097(5) 0.271(2) 0.2752(6) 0.030 Uiso 0.12 1 d D U P A 2
C4A C 0.6888(5) 0.414(2) 0.3320(6) 0.030 Uiso 0.12 1 d D U P A 2
H4A1 H 0.6786 0.3070 0.3687 0.036 Uiso 0.12 1 calc R U P A 2
H4A2 H 0.6470 0.4984 0.3108 0.036 Uiso 0.12 1 calc R U P A 2
C5A C 0.7408(6) 0.587(3) 0.3674(11) 0.030 Uiso 0.12 1 d D U P A 2
H5A1 H 0.7283 0.6438 0.4114 0.036 Uiso 0.12 1 calc R U P A 2
H5A2 H 0.7399 0.7228 0.3353 0.036 Uiso 0.12 1 calc R U P A 2
C6A C 0.8128(5) 0.491(2) 0.3865(7) 0.030 Uiso 0.12 1 d D U P A 2
H6A H 0.8169 0.3647 0.4229 0.036 Uiso 0.12 1 calc R U P A 2
C13A C 0.8597(6) 0.696(2) 0.4140(7) 0.030 Uiso 0.12 1 d D U P A 2
H13D H 0.8658 0.7922 0.3739 0.045 Uiso 0.12 1 calc R U P A 2
H13E H 0.9033 0.6356 0.4392 0.045 Uiso 0.12 1 calc R U P A 2
H13F H 0.8398 0.7903 0.4467 0.045 Uiso 0.12 1 calc R U P A 2
C7 C 0.55764(7) 0.1893(3) 0.15440(7) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.48834(7) 0.2534(3) 0.14223(8) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.43872(7) 0.1212(3) 0.09925(8) 0.0231(3) Uani 1 1 d . . . . .
H9 H 0.3930 0.1683 0.0910 0.028 Uiso 1 1 calc R U . . .
C10 C 0.45670(7) -0.0784(3) 0.06888(8) 0.0238(3) Uani 1 1 d . . . . .
C11 C 0.52397(7) -0.1511(3) 0.07986(8) 0.0249(3) Uani 1 1 d . . . . .
H11 H 0.5353 -0.2907 0.0585 0.030 Uiso 1 1 calc R U . . .
C12 C 0.57297(7) -0.0194(3) 0.12143(8) 0.0251(3) Uani 1 1 d . . . . .
H12 H 0.6184 -0.0686 0.1285 0.030 Uiso 1 1 calc R U . . .
C14 C 0.90018(7) 0.2881(3) 0.34103(9) 0.0307(4) Uani 1 1 d . . . . .
C15 C 0.93109(8) 0.1244(3) 0.39084(10) 0.0363(4) Uani 1 1 d . . . . .
H15 H 0.9047 0.0382 0.4170 0.044 Uiso 1 1 calc R U . . .
C16 C 0.99995(8) 0.0847(3) 0.40304(9) 0.0341(4) Uani 1 1 d . . . . .
H16 H 1.0198 -0.0271 0.4376 0.041 Uiso 1 1 calc R U . . .
C17 C 1.04062(7) 0.2067(3) 0.36519(8) 0.0252(3) Uani 1 1 d . . . . .
C18 C 1.00932(7) 0.3659(3) 0.31410(9) 0.0292(3) Uani 1 1 d . . . . .
H18 H 1.0354 0.4485 0.2868 0.035 Uiso 1 1 calc R U . . .
C19 C 0.94036(8) 0.4060(3) 0.30235(9) 0.0317(4) Uani 1 1 d . . . . .
H19 H 0.9203 0.5160 0.2672 0.038 Uiso 1 1 calc R U . . .
C20 C 1.11479(7) 0.1695(3) 0.38091(8) 0.0237(3) Uani 1 1 d . . . . .
C21 C 1.14327(7) -0.0372(3) 0.41206(8) 0.0274(3) Uani 1 1 d . . . . .
H21 H 1.1147 -0.1605 0.4203 0.033 Uiso 1 1 calc R U . . .
C22 C 1.21237(8) -0.0660(3) 0.43111(9) 0.0314(3) Uani 1 1 d . . . . .
H22 H 1.2306 -0.2072 0.4528 0.038 Uiso 1 1 calc R U . . .
C23 C 1.25503(7) 0.1110(3) 0.41863(9) 0.0326(4) Uani 1 1 d . . . . .
H23 H 1.3024 0.0921 0.4323 0.039 Uiso 1 1 calc R U . . .
C24 C 1.22799(7) 0.3147(3) 0.38621(9) 0.0310(3) Uani 1 1 d . . . . .
H24 H 1.2568 0.4351 0.3766 0.037 Uiso 1 1 calc R U . . .
C25 C 1.15824(7) 0.3438(3) 0.36756(8) 0.0269(3) Uani 1 1 d . . . . .
H25 H 1.1402 0.4846 0.3454 0.032 Uiso 1 1 calc R U . . .
N1 N 0.67276(6) 0.2473(3) 0.20678(7) 0.0288(3) Uani 1 1 d . . . . .
N2 N 0.60631(6) 0.3190(2) 0.19469(7) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.46569(6) 0.4559(2) 0.17535(7) 0.0245(3) Uani 1 1 d . . . . .
N4 N 0.40433(6) -0.2156(2) 0.02412(7) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.50801(5) 0.58479(19) 0.21277(6) 0.0274(2) Uani 1 1 d . . . . .
O2 O 0.40499(5) 0.4957(2) 0.16522(6) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.34659(5) -0.1390(2) 0.01075(7) 0.0368(3) Uani 1 1 d . . . . .
O4 O 0.42039(6) -0.4037(2) 0.00123(6) 0.0341(3) Uani 1 1 d . . . . .
H2N H 0.5920(10) 0.446(4) 0.2171(11) 0.042(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.527(2) . ?
C1 C2 1.535(2) . ?
C1 C6 1.543(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.508(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.290(2) . ?
C3 C4 1.504(3) . ?
C4 C5 1.524(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C13 1.529(2) . ?
C6 H6 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C1A C2A 1.540(9) . ?
C1A C14 1.549(15) . ?
C1A C6A 1.559(9) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.515(9) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A N1 1.377(11) . ?
C3A C4A 1.495(9) . ?
C4A C5A 1.506(9) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.538(9) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C13A 1.534(9) . ?
C6A H6A 1.0000 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C7 N2 1.3449(19) . ?
C7 C12 1.420(2) . ?
C7 C8 1.4292(19) . ?
C8 C9 1.387(2) . ?
C8 N3 1.4470(19) . ?
C9 C10 1.370(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4046(19) . ?
C10 N4 1.4515(19) . ?
C11 C12 1.366(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C19 1.393(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.402(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(2) . ?
C17 C20 1.4918(19) . ?
C18 C19 1.394(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.395(2) . ?
C20 C21 1.397(2) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 N2 1.3862(16) . ?
N2 H2N 0.93(2) . ?
N3 O2 1.2315(15) . ?
N3 O1 1.2420(16) . ?
N4 O3 1.2303(16) . ?
N4 O4 1.2353(18) . ?

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
C14 C1 C2 110.78(14) . . ?
C14 C1 C6 111.02(14) . . ?
C2 C1 C6 111.16(15) . . ?
C14 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
C6 C1 H1 107.9 . . ?
C3 C2 C1 112.89(14) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 128.93(15) . . ?
N1 C3 C2 116.35(16) . . ?
C4 C3 C2 114.72(15) . . ?
C3 C4 C5 110.57(16) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 112.78(17) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C13 C6 C5 110.26(15) . . ?
C13 C6 C1 111.27(16) . . ?
C5 C6 C1 110.26(15) . . ?
C13 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C1 C6 H6 108.3 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2A C1A C14 105.1(9) . . ?
C2A C1A C6A 106.9(8) . . ?
C14 C1A C6A 103.5(9) . . ?
C2A C1A H1A 113.5 . . ?
C14 C1A H1A 113.5 . . ?
C6A C1A H1A 113.5 . . ?
C3A C2A C1A 110.5(9) . . ?
C3A C2A H2A1 109.6 . . ?
C1A C2A H2A1 109.6 . . ?
C3A C2A H2A2 109.6 . . ?
C1A C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.1 . . ?
N1 C3A C4A 124.8(9) . . ?
N1 C3A C2A 118.6(8) . . ?
C4A C3A C2A 115.5(8) . . ?
C3A C4A C5A 114.1(9) . . ?
C3A C4A H4A1 108.7 . . ?
C5A C4A H4A1 108.7 . . ?
C3A C4A H4A2 108.7 . . ?
C5A C4A H4A2 108.7 . . ?
H4A1 C4A H4A2 107.6 . . ?
C4A C5A C6A 114.5(10) . . ?
C4A C5A H5A1 108.6 . . ?
C6A C5A H5A1 108.6 . . ?
C4A C5A H5A2 108.6 . . ?
C6A C5A H5A2 108.6 . . ?
H5A1 C5A H5A2 107.6 . . ?
C13A C6A C5A 107.5(9) . . ?
C13A C6A C1A 109.0(9) . . ?
C5A C6A C1A 106.9(10) . . ?
C13A C6A H6A 111.1 . . ?
C5A C6A H6A 111.1 . . ?
C1A C6A H6A 111.1 . . ?
C6A C13A H13D 109.5 . . ?
C6A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C6A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N2 C7 C12 121.22(13) . . ?
N2 C7 C8 122.21(14) . . ?
C12 C7 C8 116.58(13) . . ?
C9 C8 C7 121.73(14) . . ?
C9 C8 N3 116.16(12) . . ?
C7 C8 N3 122.09(13) . . ?
C10 C9 C8 118.93(13) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.66(13) . . ?
C9 C10 N4 118.44(13) . . ?
C11 C10 N4 119.89(14) . . ?
C12 C11 C10 119.44(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 121.65(13) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C15 C14 C19 117.64(14) . . ?
C15 C14 C1 119.10(15) . . ?
C19 C14 C1 123.21(15) . . ?
C15 C14 C1A 137.8(5) . . ?
C19 C14 C1A 104.5(5) . . ?
C16 C15 C14 121.20(16) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 121.17(16) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.50(14) . . ?
C18 C17 C20 121.88(14) . . ?
C16 C17 C20 120.60(14) . . ?
C17 C18 C19 121.11(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 121.34(15) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C25 C20 C21 117.72(13) . . ?
C25 C20 C17 121.03(14) . . ?
C21 C20 C17 121.20(13) . . ?
C22 C21 C20 121.28(14) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.29(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.44(14) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.10(15) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 121.14(15) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C3 N1 N2 114.99(14) . . ?
C3A N1 N2 116.4(4) . . ?
C7 N2 N1 120.39(13) . . ?
C7 N2 H2N 115.9(13) . . ?
N1 N2 H2N 123.3(13) . . ?
O2 N3 O1 122.06(13) . . ?
O2 N3 C8 118.89(12) . . ?
O1 N3 C8 119.05(11) . . ?
O3 N4 O4 123.47(13) . . ?
O3 N4 C10 118.64(13) . . ?
O4 N4 C10 117.89(12) . . ?

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
C14 C1 C2 C3 -175.00(15) . . . . ?
C6 C1 C2 C3 -51.1(2) . . . . ?
C1 C2 C3 N1 -130.38(18) . . . . ?
C1 C2 C3 C4 50.6(2) . . . . ?
N1 C3 C4 C5 129.9(2) . . . . ?
C2 C3 C4 C5 -51.2(2) . . . . ?
C3 C4 C5 C6 54.4(2) . . . . ?
C4 C5 C6 C13 -179.80(17) . . . . ?
C4 C5 C6 C1 -56.5(2) . . . . ?
C14 C1 C6 C13 -59.75(19) . . . . ?
C2 C1 C6 C13 176.45(15) . . . . ?
C14 C1 C6 C5 177.58(16) . . . . ?
C2 C1 C6 C5 53.8(2) . . . . ?
C14 C1A C2A C3A 172.3(9) . . . . ?
C6A C1A C2A C3A 62.8(14) . . . . ?
C1A C2A C3A N1 117.7(12) . . . . ?
C1A C2A C3A C4A -50.6(15) . . . . ?
N1 C3A C4A C5A -127.2(14) . . . . ?
C2A C3A C4A C5A 40.2(17) . . . . ?
C3A C4A C5A C6A -44(2) . . . . ?
C4A C5A C6A C13A 173.8(15) . . . . ?
C4A C5A C6A C1A 56.9(18) . . . . ?
C2A C1A C6A C13A 179.0(11) . . . . ?
C14 C1A C6A C13A 68.4(11) . . . . ?
C2A C1A C6A C5A -65.1(13) . . . . ?
C14 C1A C6A C5A -175.7(10) . . . . ?
N2 C7 C8 C9 178.48(14) . . . . ?
C12 C7 C8 C9 -1.3(2) . . . . ?
N2 C7 C8 N3 -3.1(2) . . . . ?
C12 C7 C8 N3 177.10(13) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
N3 C8 C9 C10 -177.18(13) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 N4 179.88(13) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
N4 C10 C11 C12 179.27(13) . . . . ?
C10 C11 C12 C7 0.4(2) . . . . ?
N2 C7 C12 C11 -179.35(14) . . . . ?
C8 C7 C12 C11 0.4(2) . . . . ?
C2 C1 C14 C15 -129.52(18) . . . . ?
C6 C1 C14 C15 106.47(19) . . . . ?
C2 C1 C14 C19 53.0(2) . . . . ?
C6 C1 C14 C19 -71.0(2) . . . . ?
C2 C1 C14 C1A 55.1(13) . . . . ?
C6 C1 C14 C1A -68.9(13) . . . . ?
C2A C1A C14 C15 -58.4(10) . . . . ?
C6A C1A C14 C15 53.6(10) . . . . ?
C2A C1A C14 C19 125.8(8) . . . . ?
C6A C1A C14 C19 -122.2(7) . . . . ?
C2A C1A C14 C1 -52.4(11) . . . . ?
C6A C1A C14 C1 59.5(12) . . . . ?
C19 C14 C15 C16 1.8(3) . . . . ?
C1 C14 C15 C16 -175.78(17) . . . . ?
C1A C14 C15 C16 -173.6(6) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C15 C16 C17 C20 177.47(16) . . . . ?
C16 C17 C18 C19 1.5(2) . . . . ?
C20 C17 C18 C19 -177.08(15) . . . . ?
C15 C14 C19 C18 -1.5(3) . . . . ?
C1 C14 C19 C18 176.04(16) . . . . ?
C1A C14 C19 C18 175.4(4) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C18 C17 C20 C25 25.1(2) . . . . ?
C16 C17 C20 C25 -153.49(16) . . . . ?
C18 C17 C20 C21 -157.48(15) . . . . ?
C16 C17 C20 C21 24.0(2) . . . . ?
C25 C20 C21 C22 2.0(2) . . . . ?
C17 C20 C21 C22 -175.59(15) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C21 C20 C25 C24 -1.5(2) . . . . ?
C17 C20 C25 C24 176.09(14) . . . . ?
C23 C24 C25 C20 -0.2(2) . . . . ?
C4 C3 N1 C3A -100.6(7) . . . . ?
C2 C3 N1 C3A 80.5(6) . . . . ?
C4 C3 N1 N2 1.6(3) . . . . ?
C2 C3 N1 N2 -177.33(14) . . . . ?
C4A C3A N1 C3 84.3(13) . . . . ?
C2A C3A N1 C3 -82.8(11) . . . . ?
C4A C3A N1 N2 -14.1(15) . . . . ?
C2A C3A N1 N2 178.8(8) . . . . ?
C12 C7 N2 N1 -2.0(2) . . . . ?
C8 C7 N2 N1 178.22(13) . . . . ?
C3 N1 N2 C7 177.35(15) . . . . ?
C3A N1 N2 C7 -137.2(7) . . . . ?
C9 C8 N3 O2 1.72(19) . . . . ?
C7 C8 N3 O2 -176.75(13) . . . . ?
C9 C8 N3 O1 -177.92(13) . . . . ?
C7 C8 N3 O1 3.6(2) . . . . ?
C9 C10 N4 O3 5.4(2) . . . . ?
C11 C10 N4 O3 -174.31(14) . . . . ?
C9 C10 N4 O4 -174.84(13) . . . . ?
C11 C10 N4 O4 5.5(2) . . . . ?

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
N2 H2N O1 0.93(2) 1.87(2) 2.5986(17) 133.6(18) .

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1058345'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'meso L1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N2 O4 S4'
_chemical_formula_sum            'C28 H28 N2 O4 S4'
_chemical_formula_weight         584.76

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'
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'
N N 0.0061 0.0033 '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                   6.5498(4)
_cell_length_b                   20.4037(13)
_cell_length_c                   11.0725(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.469(3)
_cell_angle_gamma                90
_cell_volume                     1455.10(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.8

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20450
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.317
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3345
_reflns_number_gt                2715
_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_refine_special_details          
;
 The molecule resides around a crystallographic inversion center at 
1/2, 1/2, 1/2.
 The toluene portion of the molecule was disordered about two orientations.  
The disorder was modeled by assigning the variable x to the site occupancy 
factors for one component of the disorder and (1-x) to the site 
occupancy factor to the alternate component.  A common isotropic 
displacement parameter was refined for all atoms involved in the disorder 
while refining x.  The geometry of the two components were restrained to 
be equivalent throughout the refinement process.  In this way, the site 
occupancy for the major component consisting of atoms, C1, C2, C3, C4, 
C5, C6 and C7 refined to 52.7(3)%.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+1.0202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     265
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.003

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
C1 C 0.950(4) 0.5291(11) 0.757(2) 0.020(2) Uani 0.527 1 d . U P A 1
C2 C 1.008(2) 0.4653(10) 0.7584(16) 0.028(2) Uani 0.527 1 d . U P A 1
H2 H 1.1056 0.4531 0.7087 0.034 Uiso 0.527 1 calc R U P A 1
C3 C 0.9350(14) 0.4167(7) 0.8265(13) 0.034(2) Uani 0.527 1 d . U P A 1
H3 H 0.9828 0.3728 0.8234 0.041 Uiso 0.527 1 calc R U P A 1
C4 C 0.7931(14) 0.4325(5) 0.8981(11) 0.0378(18) Uani 0.527 1 d . U P A 1
C5 C 0.7259(16) 0.4960(4) 0.8989(10) 0.0410(17) Uani 0.527 1 d . U P A 1
H5 H 0.6265 0.5066 0.9485 0.049 Uiso 0.527 1 calc R U P A 1
C6 C 0.795(2) 0.5450(6) 0.8319(13) 0.0319(17) Uani 0.527 1 d . U P A 1
H6 H 0.7421 0.5884 0.8339 0.038 Uiso 0.527 1 calc R U P A 1
C7 C 0.7100(18) 0.3774(6) 0.9701(14) 0.063(3) Uani 0.527 1 d . U P A 1
H7A H 0.6691 0.3400 0.9154 0.094 Uiso 0.527 1 calc R U P A 1
H7B H 0.5892 0.3932 1.0023 0.094 Uiso 0.527 1 calc R U P A 1
H7C H 0.8186 0.3637 1.0384 0.094 Uiso 0.527 1 calc R U P A 1
C1A C 0.944(5) 0.5253(13) 0.767(2) 0.022(2) Uani 0.473 1 d . U P A 2
C2A C 1.045(2) 0.4643(10) 0.7480(18) 0.0235(18) Uani 0.473 1 d . U P A 2
H2A H 1.1396 0.4602 0.6931 0.028 Uiso 0.473 1 calc R U P A 2
C3A C 0.9910(17) 0.4124(8) 0.8165(14) 0.034(2) Uani 0.473 1 d . U P A 2
H3A H 1.0539 0.3710 0.8088 0.041 Uiso 0.473 1 calc R U P A 2
C4A C 0.8500(16) 0.4176(5) 0.8957(12) 0.0359(19) Uani 0.473 1 d . U P A 2
C5A C 0.7670(17) 0.4783(5) 0.9127(11) 0.0408(19) Uani 0.473 1 d . U P A 2
H5A H 0.6738 0.4835 0.9684 0.049 Uiso 0.473 1 calc R U P A 2
C6A C 0.822(3) 0.5328(7) 0.8465(15) 0.034(2) Uani 0.473 1 d . U P A 2
H6A H 0.7691 0.5750 0.8600 0.041 Uiso 0.473 1 calc R U P A 2
C7A C 0.7891(19) 0.3607(6) 0.9686(13) 0.059(3) Uani 0.473 1 d . U P A 2
H7A1 H 0.7546 0.3769 1.0458 0.089 Uiso 0.473 1 calc R U P A 2
H7A2 H 0.9051 0.3298 0.9865 0.089 Uiso 0.473 1 calc R U P A 2
H7A3 H 0.6680 0.3385 0.9208 0.089 Uiso 0.473 1 calc R U P A 2
C8 C 0.4796(3) 0.53047(8) 0.46037(17) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.5467(3) 0.66233(8) 0.43528(17) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.3435(3) 0.68397(9) 0.41745(19) 0.0227(4) Uani 1 1 d . . . . .
C11 C 0.2859(3) 0.73601(9) 0.3381(2) 0.0269(4) Uani 1 1 d . . . . .
C12 C 0.4299(4) 0.76588(10) 0.2803(2) 0.0339(5) Uani 1 1 d . . . . .
C13 C 0.6317(4) 0.74361(12) 0.2990(3) 0.0473(7) Uani 1 1 d . . . . .
C14 C 0.6922(3) 0.69122(11) 0.3775(2) 0.0371(6) Uani 1 1 d . . . . .
O1 O 1.2166(2) 0.57857(6) 0.64380(12) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.9715(2) 0.65131(6) 0.72230(13) 0.0256(3) Uani 1 1 d . . . . .
S1 S 1.01027(7) 0.59010(2) 0.66584(4) 0.01579(12) Uani 1 1 d . . . . .
S2 S 0.61932(6) 0.59773(2) 0.54329(4) 0.01515(12) Uani 1 1 d . . . . .
N1 N 0.8588(2) 0.58001(7) 0.53474(13) 0.0159(3) Uani 1 1 d . . . . .
H8A H 0.531(3) 0.5267(9) 0.3864(19) 0.017(5) Uiso 1 1 d . . . . .
H8B H 0.337(3) 0.5426(10) 0.4460(18) 0.021(5) Uiso 1 1 d . . . . .
H10 H 0.247(4) 0.6655(11) 0.461(2) 0.030(6) Uiso 1 1 d . . . . .
H11 H 0.146(4) 0.7516(11) 0.325(2) 0.037(7) Uiso 1 1 d . . . . .
H12 H 0.389(4) 0.8004(12) 0.232(2) 0.036(6) Uiso 1 1 d . . . . .
H13 H 0.726(5) 0.7652(16) 0.262(3) 0.076(10) Uiso 1 1 d . . . . .
H14 H 0.826(4) 0.6766(12) 0.389(2) 0.041(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.36(3) . ?
C1 C6 1.46(3) . ?
C1 S1 1.70(2) . ?
C2 C3 1.382(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(10) . ?
C4 C7 1.535(16) . ?
C5 C6 1.369(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C1A C6A 1.30(3) . ?
C1A C2A 1.44(4) . ?
C1A S1 1.84(2) . ?
C2A C3A 1.39(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(13) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.380(11) . ?
C4A C7A 1.508(17) . ?
C5A C6A 1.413(15) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8 C8 1.517(3) 3_666 ?
C8 S2 1.8052(17) . ?
C8 H8A 0.94(2) . ?
C8 H8B 0.95(2) . ?
C9 C14 1.373(3) . ?
C9 C10 1.382(3) . ?
C9 S2 1.7851(18) . ?
C10 C11 1.386(3) . ?
C10 H10 0.94(2) . ?
C11 C12 1.375(3) . ?
C11 H11 0.96(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.89(2) . ?
C13 C14 1.390(3) . ?
C13 H13 0.92(3) . ?
C14 H14 0.92(3) . ?
O1 S1 1.4358(13) . ?
O2 S1 1.4398(13) . ?
S1 N1 1.6155(15) . ?
S2 N1 1.6294(15) . ?

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 115.5(18) . . ?
C2 C1 S1 128.1(18) . . ?
C6 C1 S1 115.9(14) . . ?
C1 C2 C3 124.9(16) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C4 C3 C2 119.0(10) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 118.8(10) . . ?
C3 C4 C7 118.1(9) . . ?
C5 C4 C7 123.1(9) . . ?
C4 C5 C6 123.4(10) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C1 118.4(11) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6A C1A C2A 124(2) . . ?
C6A C1A S1 124.9(18) . . ?
C2A C1A S1 111.4(19) . . ?
C3A C2A C1A 114.3(16) . . ?
C3A C2A H2A 122.8 . . ?
C1A C2A H2A 122.9 . . ?
C2A C3A C4A 123.4(12) . . ?
C2A C3A H3A 118.3 . . ?
C4A C3A H3A 118.3 . . ?
C5A C4A C3A 118.6(10) . . ?
C5A C4A C7A 118.0(10) . . ?
C3A C4A C7A 123.4(9) . . ?
C4A C5A C6A 119.5(10) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
C1A C6A C5A 120.2(14) . . ?
C1A C6A H6A 119.9 . . ?
C5A C6A H6A 119.9 . . ?
C4A C7A H7A1 109.5 . . ?
C4A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C4A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C8 C8 S2 108.00(17) 3_666 . ?
C8 C8 H8A 112.4(12) 3_666 . ?
S2 C8 H8A 106.1(12) . . ?
C8 C8 H8B 112.0(12) 3_666 . ?
S2 C8 H8B 106.2(12) . . ?
H8A C8 H8B 111.7(17) . . ?
C14 C9 C10 121.88(18) . . ?
C14 C9 S2 120.39(15) . . ?
C10 C9 S2 117.64(14) . . ?
C9 C10 C11 118.65(19) . . ?
C9 C10 H10 121.3(14) . . ?
C11 C10 H10 119.9(14) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 120.1(14) . . ?
C10 C11 H11 119.7(15) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 118.1(16) . . ?
C13 C12 H12 121.6(16) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119(2) . . ?
C14 C13 H13 121(2) . . ?
C9 C14 C13 118.6(2) . . ?
C9 C14 H14 121.5(16) . . ?
C13 C14 H14 119.9(16) . . ?
O1 S1 O2 117.50(8) . . ?
O1 S1 N1 105.64(8) . . ?
O2 S1 N1 111.89(8) . . ?
O1 S1 C1 108.0(9) . . ?
O2 S1 C1 107.4(8) . . ?
N1 S1 C1 105.8(9) . . ?
O1 S1 C1A 108.7(10) . . ?
O2 S1 C1A 106.2(9) . . ?
N1 S1 C1A 106.5(9) . . ?
N1 S2 C9 105.49(8) . . ?
N1 S2 C8 101.91(8) . . ?
C9 S2 C8 99.89(8) . . ?
S1 N1 S2 111.09(9) . . ?

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
C6 C1 C2 C3 -2(3) . . . . ?
S1 C1 C2 C3 -172.6(14) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 0.8(14) . . . . ?
C2 C3 C4 C7 178.4(11) . . . . ?
C3 C4 C5 C6 -0.5(14) . . . . ?
C7 C4 C5 C6 -177.9(10) . . . . ?
C4 C5 C6 C1 -1.1(18) . . . . ?
C2 C1 C6 C5 2(3) . . . . ?
S1 C1 C6 C5 174.0(12) . . . . ?
C6A C1A C2A C3A 4(4) . . . . ?
S1 C1A C2A C3A -176.2(13) . . . . ?
C1A C2A C3A C4A 1(2) . . . . ?
C2A C3A C4A C5A -3.7(16) . . . . ?
C2A C3A C4A C7A 179.0(13) . . . . ?
C3A C4A C5A C6A 2.1(14) . . . . ?
C7A C4A C5A C6A 179.6(10) . . . . ?
C2A C1A C6A C5A -5(4) . . . . ?
S1 C1A C6A C5A 174.5(15) . . . . ?
C4A C5A C6A C1A 2(2) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
S2 C9 C10 C11 177.18(15) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
S2 C9 C14 C13 -176.7(2) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C2 C1 S1 O1 -35(3) . . . . ?
C6 C1 S1 O1 154.6(14) . . . . ?
C2 C1 S1 O2 -162(2) . . . . ?
C6 C1 S1 O2 27.0(18) . . . . ?
C2 C1 S1 N1 78(2) . . . . ?
C6 C1 S1 N1 -92.6(15) . . . . ?
C2 C1 S1 C1A -160(93) . . . . ?
C6 C1 S1 C1A 30(90) . . . . ?
C6A C1A S1 O1 149(2) . . . . ?
C2A C1A S1 O1 -31(2) . . . . ?
C6A C1A S1 O2 22(3) . . . . ?
C2A C1A S1 O2 -158.6(17) . . . . ?
C6A C1A S1 N1 -98(2) . . . . ?
C2A C1A S1 N1 82(2) . . . . ?
C6A C1A S1 C1 -156(92) . . . . ?
C2A C1A S1 C1 24(88) . . . . ?
C14 C9 S2 N1 -7.7(2) . . . . ?
C10 C9 S2 N1 175.60(14) . . . . ?
C14 C9 S2 C8 -113.09(19) . . . . ?
C10 C9 S2 C8 70.20(16) . . . . ?
C8 C8 S2 N1 72.32(19) 3_666 . . . ?
C8 C8 S2 C9 -179.39(18) 3_666 . . . ?
O1 S1 N1 S2 -175.16(8) . . . . ?
O2 S1 N1 S2 -46.16(11) . . . . ?
C1 S1 N1 S2 70.5(9) . . . . ?
C1A S1 N1 S2 69.4(10) . . . . ?
C9 S2 N1 S1 120.55(9) . . . . ?
C8 S2 N1 S1 -135.53(9) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1058346'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'racemic L1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C28H28N2O4S4
_chemical_formula_sum            'C28 H28 N2 O4 S4'
_chemical_formula_weight         584.76

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   15.181(6)
_cell_length_b                   15.559(5)
_cell_length_c                   23.696(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.016(18)
_cell_angle_gamma                90
_cell_volume                     5406(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.390
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26405
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.583
_diffrn_reflns_theta_max         32.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8824
_reflns_number_gt                7408
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.4197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8824
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.008
_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
C1 C 0.49309(10) 0.32233(9) 0.94185(6) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.57484(11) 0.32356(10) 0.92519(7) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.6312 0.3334 0.9532 0.021 Uiso 1 1 calc R U . . .
C3 C 0.57200(11) 0.31016(10) 0.86671(7) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.6270 0.3104 0.8547 0.024 Uiso 1 1 calc R U . . .
C4 C 0.48922(11) 0.29639(10) 0.82572(7) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.4878 0.2878 0.7858 0.025 Uiso 1 1 calc R U . . .
C5 C 0.40855(11) 0.29525(10) 0.84323(7) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.3522 0.2863 0.8150 0.025 Uiso 1 1 calc R U . . .
C6 C 0.40943(10) 0.30709(10) 0.90171(7) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.3546 0.3049 0.9139 0.021 Uiso 1 1 calc R U . . .
C7 C 0.39308(10) 0.38443(10) 1.01618(6) 0.0162(3) Uani 1 1 d . . . . .
H7A H 0.3793 0.4291 0.9854 0.019 Uiso 1 1 calc R U . . .
H7B H 0.3444 0.3404 1.0063 0.019 Uiso 1 1 calc R U . . .
C8 C 0.65462(10) 0.39678(9) 1.15323(6) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.66231(11) 0.32358(10) 1.18789(7) 0.0194(3) Uani 1 1 d . . . . .
H9 H 0.6753 0.2694 1.1734 0.023 Uiso 1 1 calc R U . . .
C10 C 0.65069(12) 0.33096(11) 1.24412(7) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.6557 0.2811 1.2679 0.028 Uiso 1 1 calc R U . . .
C11 C 0.63193(11) 0.40954(11) 1.26615(7) 0.0226(3) Uani 1 1 d . . . . .
C12 C 0.62412(12) 0.48252(11) 1.23028(7) 0.0235(3) Uani 1 1 d . . . . .
H12 H 0.6108 0.5367 1.2446 0.028 Uiso 1 1 calc R U . . .
C13 C 0.63548(12) 0.47665(10) 1.17449(7) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.6304 0.5265 1.1507 0.026 Uiso 1 1 calc R U . . .
C14 C 0.61953(14) 0.41803(14) 1.32697(8) 0.0334(4) Uani 1 1 d . . . . .
H14A H 0.5546 0.4249 1.3248 0.050 Uiso 1 1 calc R U . . .
H14B H 0.6531 0.4684 1.3461 0.050 Uiso 1 1 calc R U . . .
H14C H 0.6428 0.3663 1.3496 0.050 Uiso 1 1 calc R U . . .
C15 C 0.37925(10) 0.40567(10) 1.18900(6) 0.0164(3) Uani 1 1 d . . . . .
C16 C 0.34453(11) 0.36005(10) 1.22887(7) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.3320 0.3003 1.2235 0.025 Uiso 1 1 calc R U . . .
C17 C 0.32834(12) 0.40303(11) 1.27672(7) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.3042 0.3728 1.3042 0.029 Uiso 1 1 calc R U . . .
C18 C 0.34753(12) 0.48999(12) 1.28428(7) 0.0256(3) Uani 1 1 d . . . . .
H18 H 0.3366 0.5191 1.3171 0.031 Uiso 1 1 calc R U . . .
C19 C 0.38253(13) 0.53488(11) 1.24439(7) 0.0281(4) Uani 1 1 d . . . . .
H19 H 0.3955 0.5945 1.2499 0.034 Uiso 1 1 calc R U . . .
C20 C 0.39872(12) 0.49274(10) 1.19626(7) 0.0230(3) Uani 1 1 d . . . . .
H20 H 0.4227 0.5231 1.1688 0.028 Uiso 1 1 calc R U . . .
C21 C 0.39451(11) 0.42459(9) 1.07476(6) 0.0174(3) Uani 1 1 d . . . . .
H21A H 0.3368 0.4563 1.0714 0.021 Uiso 1 1 calc R U . . .
H21B H 0.4453 0.4664 1.0854 0.021 Uiso 1 1 calc R U . . .
C22 C 0.42508(11) 0.14985(9) 1.08106(6) 0.0164(3) Uani 1 1 d . . . . .
C23 C 0.51760(11) 0.14119(10) 1.10842(7) 0.0215(3) Uani 1 1 d . . . . .
H23 H 0.5390 0.1483 1.1495 0.026 Uiso 1 1 calc R U . . .
C24 C 0.57867(12) 0.12211(11) 1.07539(8) 0.0256(3) Uani 1 1 d . . . . .
H24 H 0.6418 0.1168 1.0941 0.031 Uiso 1 1 calc R U . . .
C25 C 0.54798(13) 0.11066(10) 1.01503(8) 0.0245(3) Uani 1 1 d . . . . .
C26 C 0.45505(13) 0.11867(10) 0.98853(7) 0.0229(3) Uani 1 1 d . . . . .
H26 H 0.4335 0.1103 0.9475 0.027 Uiso 1 1 calc R U . . .
C27 C 0.39320(11) 0.13857(10) 1.02072(7) 0.0196(3) Uani 1 1 d . . . . .
H27 H 0.3301 0.1444 1.0020 0.024 Uiso 1 1 calc R U . . .
C28 C 0.61502(15) 0.09255(13) 0.97934(9) 0.0367(5) Uani 1 1 d . . . . .
H28A H 0.5843 0.0610 0.9439 0.055 Uiso 1 1 calc R U . . .
H28B H 0.6655 0.0579 1.0024 0.055 Uiso 1 1 calc R U . . .
H28C H 0.6388 0.1469 0.9685 0.055 Uiso 1 1 calc R U . . .
N1 N 0.57234(8) 0.41611(8) 1.03729(5) 0.0151(2) Uani 1 1 d . . . . .
N2 N 0.32143(8) 0.28042(8) 1.10651(5) 0.0160(2) Uani 1 1 d . . . . .
O1 O 0.69875(8) 0.30464(8) 1.07339(5) 0.0232(2) Uani 1 1 d . . . . .
O2 O 0.72901(8) 0.46129(8) 1.07631(5) 0.0263(3) Uani 1 1 d . . . . .
O3 O 0.39580(8) 0.16883(7) 1.18306(5) 0.0209(2) Uani 1 1 d . . . . .
O4 O 0.26359(8) 0.13356(8) 1.10048(5) 0.0223(2) Uani 1 1 d . . . . .
S1 S 0.50268(2) 0.33502(2) 1.01832(2) 0.01249(8) Uani 1 1 d . . . . .
S2 S 0.66939(2) 0.39109(2) 1.08165(2) 0.01640(9) Uani 1 1 d . . . . .
S3 S 0.40822(2) 0.34454(2) 1.13209(2) 0.01429(8) Uani 1 1 d . . . . .
S4 S 0.34773(3) 0.18016(2) 1.12212(2) 0.01562(8) 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 1.396(2) . ?
C1 C2 1.397(2) . ?
C1 S1 1.7906(16) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C21 1.517(2) . ?
C7 S1 1.8216(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.391(2) . ?
C8 C13 1.399(2) . ?
C8 S2 1.7698(16) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.405(2) . ?
C11 C14 1.507(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.388(2) . ?
C15 C16 1.390(2) . ?
C15 S3 1.7953(16) . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 S3 1.8150(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.393(2) . ?
C22 C27 1.397(2) . ?
C22 S4 1.7721(16) . ?
C23 C24 1.391(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(3) . ?
C25 C28 1.509(2) . ?
C26 C27 1.389(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 S2 1.6201(14) . ?
N1 S1 1.6328(13) . ?
N2 S4 1.6288(14) . ?
N2 S3 1.6386(14) . ?
O1 S2 1.4462(13) . ?
O2 S2 1.4449(12) . ?
O3 S4 1.4500(12) . ?
O4 S4 1.4425(13) . ?

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 121.88(14) . . ?
C6 C1 S1 121.96(12) . . ?
C2 C1 S1 116.06(11) . . ?
C3 C2 C1 118.63(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.52(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.96(15) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.80(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.19(14) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C21 C7 S1 110.61(10) . . ?
C21 C7 H7A 109.5 . . ?
S1 C7 H7A 109.5 . . ?
C21 C7 H7B 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C13 120.52(14) . . ?
C9 C8 S2 120.85(12) . . ?
C13 C8 S2 118.63(12) . . ?
C8 C9 C10 119.02(15) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 121.43(15) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 118.55(15) . . ?
C10 C11 C14 121.71(16) . . ?
C12 C11 C14 119.74(16) . . ?
C13 C12 C11 120.95(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.53(15) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 121.36(14) . . ?
C20 C15 S3 121.63(12) . . ?
C16 C15 S3 116.72(12) . . ?
C15 C16 C17 119.10(15) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 119.92(16) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.55(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 120.10(16) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.97(16) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C7 C21 S3 111.95(10) . . ?
C7 C21 H21A 109.2 . . ?
S3 C21 H21A 109.2 . . ?
C7 C21 H21B 109.2 . . ?
S3 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C27 120.30(15) . . ?
C23 C22 S4 120.13(12) . . ?
C27 C22 S4 119.50(13) . . ?
C24 C23 C22 119.82(15) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.62(16) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 118.72(16) . . ?
C26 C25 C28 121.02(17) . . ?
C24 C25 C28 120.24(18) . . ?
C27 C26 C25 121.46(16) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C22 119.07(16) . . ?
C26 C27 H27 120.5 . . ?
C22 C27 H27 120.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S2 N1 S1 114.09(8) . . ?
S4 N2 S3 111.89(8) . . ?
N1 S1 C1 103.94(7) . . ?
N1 S1 C7 101.73(7) . . ?
C1 S1 C7 100.61(7) . . ?
O2 S2 O1 117.99(8) . . ?
O2 S2 N1 104.27(7) . . ?
O1 S2 N1 113.33(7) . . ?
O2 S2 C8 106.49(7) . . ?
O1 S2 C8 107.23(7) . . ?
N1 S2 C8 106.86(7) . . ?
N2 S3 C15 105.70(7) . . ?
N2 S3 C21 102.45(7) . . ?
C15 S3 C21 101.29(7) . . ?
O4 S4 O3 117.62(7) . . ?
O4 S4 N2 104.97(7) . . ?
O3 S4 N2 111.91(7) . . ?
O4 S4 C22 108.82(7) . . ?
O3 S4 C22 106.28(8) . . ?
N2 S4 C22 106.77(7) . . ?

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
C6 C1 C2 C3 0.8(2) . . . . ?
S1 C1 C2 C3 177.16(12) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
S1 C1 C6 C5 -177.97(11) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
S2 C8 C9 C10 179.63(13) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C14 -179.84(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C14 C11 C12 C13 179.76(16) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
S2 C8 C13 C12 -179.72(13) . . . . ?
C20 C15 C16 C17 0.6(2) . . . . ?
S3 C15 C16 C17 174.51(13) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C16 C15 C20 C19 -0.3(3) . . . . ?
S3 C15 C20 C19 -173.98(13) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
S1 C7 C21 S3 -64.87(13) . . . . ?
C27 C22 C23 C24 0.7(2) . . . . ?
S4 C22 C23 C24 -176.39(12) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C23 C24 C25 C28 178.21(16) . . . . ?
C24 C25 C26 C27 0.7(2) . . . . ?
C28 C25 C26 C27 -177.51(15) . . . . ?
C25 C26 C27 C22 -0.7(2) . . . . ?
C23 C22 C27 C26 0.0(2) . . . . ?
S4 C22 C27 C26 177.07(12) . . . . ?
S2 N1 S1 C1 -113.52(8) . . . . ?
S2 N1 S1 C7 142.28(8) . . . . ?
C6 C1 S1 N1 -136.92(12) . . . . ?
C2 C1 S1 N1 46.68(13) . . . . ?
C6 C1 S1 C7 -31.88(14) . . . . ?
C2 C1 S1 C7 151.72(12) . . . . ?
C21 C7 S1 N1 -57.20(11) . . . . ?
C21 C7 S1 C1 -164.01(10) . . . . ?
S1 N1 S2 O2 160.74(8) . . . . ?
S1 N1 S2 O1 31.16(10) . . . . ?
S1 N1 S2 C8 -86.74(9) . . . . ?
C9 C8 S2 O2 -133.47(13) . . . . ?
C13 C8 S2 O2 46.19(15) . . . . ?
C9 C8 S2 O1 -6.29(15) . . . . ?
C13 C8 S2 O1 173.36(13) . . . . ?
C9 C8 S2 N1 115.53(13) . . . . ?
C13 C8 S2 N1 -64.82(14) . . . . ?
S4 N2 S3 C15 -111.62(8) . . . . ?
S4 N2 S3 C21 142.69(8) . . . . ?
C20 C15 S3 N2 -139.51(13) . . . . ?
C16 C15 S3 N2 46.56(14) . . . . ?
C20 C15 S3 C21 -32.98(15) . . . . ?
C16 C15 S3 C21 153.09(12) . . . . ?
C7 C21 S3 N2 -57.28(12) . . . . ?
C7 C21 S3 C15 -166.35(11) . . . . ?
S3 N2 S4 O4 176.09(7) . . . . ?
S3 N2 S4 O3 47.42(10) . . . . ?
S3 N2 S4 C22 -68.48(9) . . . . ?
C23 C22 S4 O4 -142.36(13) . . . . ?
C27 C22 S4 O4 40.55(14) . . . . ?
C23 C22 S4 O3 -14.78(14) . . . . ?
C27 C22 S4 O3 168.13(12) . . . . ?
C23 C22 S4 N2 104.83(13) . . . . ?
C27 C22 S4 N2 -72.27(13) . . . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.075

