# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_crys2lt6
#TrackingRef 'Kemp-benzidine.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Kemp-benzidine
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N O5 S'
_chemical_formula_sum            'C20 H26 N O5 S'
_chemical_formula_weight         392.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.5846(15)
_cell_length_b                   18.384(3)
_cell_length_c                   14.401(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.535(8)
_cell_angle_gamma                90.00
_cell_volume                     1960.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rectangular
_exptl_crystal_colour            'light red'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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 Axs Kappa ApexII CCD with Mo source'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23014
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         30.68
_reflns_number_total             6011
_reflns_number_gt                4682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       ?
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1003P)^2^+0.6325P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6011
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C 0.4210(3) 0.45716(13) 0.35984(19) 0.0621(5) Uani 1 1 d . . .
H201 H 0.3738 0.4846 0.4057 0.075 Uiso 0.7003(16) 1 calc PR A 1
H202 H 0.4318 0.4070 0.3786 0.075 Uiso 0.7003(16) 1 calc PR A 1
H203 H 0.3406 0.4613 0.2986 0.075 Uiso 0.7003(16) 1 calc PR A 1
H204 H 0.3146 0.4845 0.3631 0.075 Uiso 0.2997(16) 1 calc PR A 2
H205 H 0.5099 0.4635 0.4178 0.075 Uiso 0.2997(16) 1 calc PR A 2
H206 H 0.3908 0.4065 0.3512 0.075 Uiso 0.2997(16) 1 calc PR A 2
S1 S 0.63057(7) 0.49062(3) 0.35370(4) 0.03512(17) Uani 0.7003(16) 1 d P A 1
S2 S 0.5088(2) 0.48843(9) 0.26283(12) 0.0490(5) Uani 0.2997(16) 1 d P A 2
C19 C 0.6921(4) 0.43484(13) 0.26849(17) 0.0673(6) Uani 1 1 d . . .
H191 H 0.8090 0.4491 0.2594 0.081 Uiso 0.7003(16) 1 calc PR A 1
H192 H 0.6050 0.4395 0.2095 0.081 Uiso 0.7003(16) 1 calc PR A 1
H193 H 0.6964 0.3852 0.2896 0.081 Uiso 0.7003(16) 1 calc PR A 1
H194 H 0.7507 0.4476 0.2180 0.081 Uiso 0.2997(16) 1 d PR A 2
H195 H 0.6554 0.3848 0.2620 0.081 Uiso 0.2997(16) 1 d PR A 2
H196 H 0.7745 0.4418 0.3286 0.081 Uiso 0.2997(16) 1 d PR A 2
H101 H -0.242(3) 0.7123(10) 0.3933(13) 0.037(5) Uiso 1 1 d . . .
H102 H -0.130(2) 0.7570(10) 0.4790(13) 0.035(4) Uiso 1 1 d . . .
H151 H 0.126(3) 0.8359(11) 0.4572(15) 0.047(6) Uiso 1 1 d . . .
H131 H 0.271(3) 0.6497(11) 0.5285(13) 0.039(5) Uiso 1 1 d . . .
H132 H 0.166(3) 0.7153(11) 0.5666(14) 0.039(5) Uiso 1 1 d . . .
H152 H 0.193(3) 0.8314(12) 0.3640(17) 0.056(6) Uiso 1 1 d . . .
H6 H 0.479(4) 0.6241(15) 0.3683(19) 0.074(8) Uiso 1 1 d . . .
H3 H 0.274(4) 0.5365(14) 0.0848(19) 0.072(7) Uiso 1 1 d . . .
H5 H 0.259(4) 0.6119(17) 0.212(2) 0.092(9) Uiso 1 1 d . . .
H2 H -0.261(5) 0.5319(19) 0.032(2) 0.100(10) Uiso 1 1 d . . .
H4 H -0.263(4) 0.5994(17) 0.160(2) 0.089(9) Uiso 1 1 d . . .
N1 N -0.00601(16) 0.65597(6) 0.28146(7) 0.0273(2) Uani 1 1 d . . .
O2 O 0.04371(15) 0.55440(5) 0.37070(7) 0.0321(2) Uani 1 1 d . . .
O3 O 0.43023(16) 0.64318(7) 0.40708(10) 0.0428(3) Uani 1 1 d . . .
C11 C -0.00312(17) 0.66307(7) 0.45462(9) 0.0252(2) Uani 1 1 d . . .
O4 O 0.38750(18) 0.73739(7) 0.30842(10) 0.0488(3) Uani 1 1 d . . .
C1 C -0.0006(2) 0.52387(8) 0.04145(9) 0.0300(3) Uani 1 1 d . . .
C10 C -0.12338(19) 0.72821(8) 0.42315(10) 0.0294(3) Uani 1 1 d . . .
C7 C 0.01409(17) 0.61870(7) 0.36802(8) 0.0241(2) Uani 1 1 d . . .
C13 C 0.18407(19) 0.69007(8) 0.50764(10) 0.0301(3) Uani 1 1 d . . .
C15 C 0.1435(2) 0.80247(8) 0.40694(12) 0.0351(3) Uani 1 1 d . . .
O1 O -0.0439(2) 0.75641(7) 0.19059(8) 0.0552(4) Uani 1 1 d . . .
C12 C -0.0831(2) 0.61452(8) 0.52074(10) 0.0340(3) Uani 1 1 d . . .
H12A H -0.0866 0.6406 0.5780 0.051 Uiso 1 1 calc R . .
H12B H -0.0096 0.5718 0.5361 0.051 Uiso 1 1 calc R . .
H12C H -0.2034 0.6005 0.4897 0.051 Uiso 1 1 calc R . .
C6 C -0.0029(2) 0.61268(7) 0.19838(9) 0.0292(3) Uani 1 1 d . . .
C8 C -0.0311(2) 0.73070(8) 0.26880(10) 0.0333(3) Uani 1 1 d . . .
C18 C 0.36685(19) 0.70831(9) 0.38020(12) 0.0354(3) Uani 1 1 d . . .
C9 C -0.0444(2) 0.77527(7) 0.35549(10) 0.0311(3) Uani 1 1 d . . .
C16 C 0.27678(19) 0.74433(8) 0.45327(11) 0.0328(3) Uani 1 1 d . . .
O5 O 0.59052(19) 0.56471(7) 0.30144(12) 0.0553(4) Uani 1 1 d . . .
C14 C -0.1657(3) 0.84024(9) 0.32251(14) 0.0468(4) Uani 1 1 d . . .
H14A H -0.1134 0.8695 0.2802 0.070 Uiso 1 1 calc R . .
H14B H -0.1775 0.8688 0.3766 0.070 Uiso 1 1 calc R . .
H14C H -0.2826 0.8235 0.2899 0.070 Uiso 1 1 calc R . .
C3 C 0.1564(2) 0.54984(12) 0.09793(13) 0.0491(5) Uani 1 1 d . . .
C17 C 0.4346(2) 0.78075(11) 0.52391(15) 0.0515(5) Uani 1 1 d . . .
H17A H 0.3893 0.8042 0.5736 0.077 Uiso 1 1 calc R . .
H17B H 0.4910 0.8162 0.4909 0.077 Uiso 1 1 calc R . .
H17C H 0.5216 0.7445 0.5511 0.077 Uiso 1 1 calc R . .
C2 C -0.1599(3) 0.54539(15) 0.06476(14) 0.0620(7) Uani 1 1 d . . .
C4 C -0.1620(3) 0.58904(14) 0.14257(13) 0.0564(6) Uani 1 1 d . . .
C5 C 0.1562(2) 0.59430(12) 0.17559(14) 0.0494(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C20 0.0574(12) 0.0547(12) 0.0795(15) 0.0058(11) 0.0261(11) -0.0009(9)
S1 0.0337(3) 0.0341(3) 0.0376(3) -0.0072(2) 0.0079(2) 0.00242(19)
S2 0.0512(9) 0.0454(9) 0.0486(8) -0.0070(6) 0.0069(6) 0.0061(6)
C19 0.0985(18) 0.0472(11) 0.0655(13) -0.0060(9) 0.0379(12) 0.0210(11)
N1 0.0388(6) 0.0233(5) 0.0222(5) -0.0001(4) 0.0117(4) 0.0016(4)
O2 0.0445(6) 0.0238(5) 0.0304(5) 0.0014(4) 0.0131(4) 0.0027(4)
O3 0.0390(6) 0.0370(6) 0.0581(7) -0.0033(5) 0.0231(5) 0.0056(5)
C11 0.0293(6) 0.0257(6) 0.0229(5) -0.0021(4) 0.0108(4) -0.0016(5)
O4 0.0521(7) 0.0456(7) 0.0586(8) 0.0019(6) 0.0339(6) -0.0004(5)
C1 0.0451(7) 0.0267(6) 0.0211(5) 0.0003(5) 0.0135(5) -0.0008(5)
C10 0.0297(6) 0.0291(7) 0.0323(6) -0.0040(5) 0.0133(5) 0.0017(5)
C7 0.0266(5) 0.0248(6) 0.0225(5) 0.0009(4) 0.0092(4) -0.0010(4)
C13 0.0305(6) 0.0319(7) 0.0282(6) -0.0031(5) 0.0068(5) -0.0015(5)
C15 0.0405(8) 0.0221(6) 0.0472(8) -0.0040(6) 0.0193(6) -0.0030(5)
O1 0.1000(11) 0.0354(6) 0.0351(6) 0.0116(5) 0.0255(7) 0.0122(7)
C12 0.0446(8) 0.0355(7) 0.0262(6) -0.0003(5) 0.0167(5) -0.0070(6)
C6 0.0437(7) 0.0251(6) 0.0215(5) -0.0002(4) 0.0131(5) 0.0009(5)
C8 0.0465(8) 0.0248(7) 0.0311(6) 0.0036(5) 0.0140(6) 0.0041(6)
C18 0.0270(6) 0.0324(7) 0.0502(8) -0.0057(6) 0.0160(6) -0.0045(5)
C9 0.0375(7) 0.0229(6) 0.0354(7) -0.0005(5) 0.0136(5) 0.0040(5)
C16 0.0296(6) 0.0299(7) 0.0412(7) -0.0064(5) 0.0128(5) -0.0047(5)
O5 0.0542(7) 0.0374(7) 0.0858(10) -0.0080(6) 0.0403(7) 0.0039(6)
C14 0.0550(10) 0.0308(8) 0.0551(10) 0.0029(7) 0.0132(8) 0.0141(7)
C3 0.0412(9) 0.0609(12) 0.0479(9) -0.0267(8) 0.0156(7) 0.0014(8)
C17 0.0384(8) 0.0503(11) 0.0650(11) -0.0206(9) 0.0096(8) -0.0125(7)
C2 0.0409(9) 0.1036(19) 0.0435(9) -0.0404(11) 0.0137(7) -0.0077(10)
C4 0.0402(9) 0.0900(16) 0.0424(9) -0.0330(10) 0.0159(7) -0.0026(9)
C5 0.0399(8) 0.0611(12) 0.0484(9) -0.0299(8) 0.0122(7) -0.0039(8)

_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
C20 S1 1.725(2) . ?
C20 S2 1.769(3) . ?
C20 H201 0.9600 . ?
C20 H202 0.9600 . ?
C20 H203 0.9600 . ?
C20 H204 0.9600 . ?
C20 H205 0.9600 . ?
C20 H206 0.9600 . ?
S1 O5 1.5539(16) . ?
S1 C19 1.739(2) . ?
S1 H196 1.5166 . ?
S2 O5 1.584(2) . ?
S2 C19 1.692(3) . ?
C19 H191 0.9600 . ?
C19 H192 0.9600 . ?
C19 H193 0.9600 . ?
C19 H194 0.9600 . ?
C19 H195 0.9600 . ?
C19 H196 0.9600 . ?
N1 C8 1.3935(18) . ?
N1 C7 1.4015(16) . ?
N1 C6 1.4415(16) . ?
O2 C7 1.2021(16) . ?
O3 C18 1.317(2) . ?
O3 H6 0.81(3) . ?
C11 C10 1.5140(19) . ?
C11 C7 1.5194(17) . ?
C11 C12 1.5236(18) . ?
C11 C13 1.5410(19) . ?
O4 C18 1.204(2) . ?
C1 C3 1.374(2) . ?
C1 C2 1.380(2) . ?
C1 C1 1.483(3) 3_565 ?
C10 C9 1.520(2) . ?
C10 H101 0.95(2) . ?
C10 H102 0.973(19) . ?
C13 C16 1.530(2) . ?
C13 H131 0.99(2) . ?
C13 H132 1.00(2) . ?
C15 C16 1.522(2) . ?
C15 C9 1.540(2) . ?
C15 H151 0.98(2) . ?
C15 H152 0.95(2) . ?
O1 C8 1.2057(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C6 C5 1.360(2) . ?
C6 C4 1.367(2) . ?
C8 C9 1.515(2) . ?
C18 C16 1.525(2) . ?
C9 C14 1.519(2) . ?
C16 C17 1.545(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 C5 1.385(2) . ?
C3 H3 0.98(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C2 C4 1.381(2) . ?
C2 H2 0.85(4) . ?
C4 H4 0.87(3) . ?
C5 H5 0.90(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 C20 S2 48.27(8) . . ?
S1 C20 H201 109.5 . . ?
S2 C20 H201 129.3 . . ?
S1 C20 H202 109.5 . . ?
S2 C20 H202 120.7 . . ?
H201 C20 H202 109.5 . . ?
S1 C20 H203 109.5 . . ?
S2 C20 H203 61.4 . . ?
H201 C20 H203 109.5 . . ?
H202 C20 H203 109.5 . . ?
S1 C20 H204 127.6 . . ?
S2 C20 H204 109.5 . . ?
H201 C20 H204 41.3 . . ?
H202 C20 H204 120.7 . . ?
H203 C20 H204 68.3 . . ?
S1 C20 H205 61.3 . . ?
S2 C20 H205 109.5 . . ?
H201 C20 H205 68.5 . . ?
H202 C20 H205 82.6 . . ?
H203 C20 H205 167.3 . . ?
H204 C20 H205 109.5 . . ?
S1 C20 H206 122.4 . . ?
S2 C20 H206 109.5 . . ?
H201 C20 H206 118.9 . . ?
H202 C20 H206 26.9 . . ?
H203 C20 H206 82.7 . . ?
H204 C20 H206 109.5 . . ?
H205 C20 H206 109.5 . . ?
O5 S1 C20 104.59(10) . . ?
O5 S1 C19 103.25(10) . . ?
C20 S1 C19 102.56(13) . . ?
O5 S1 H196 118.6 . . ?
C20 S1 H196 121.4 . . ?
C19 S1 H196 33.4 . . ?
O5 S2 C19 104.10(14) . . ?
O5 S2 C20 101.31(13) . . ?
C19 S2 C20 102.66(14) . . ?
S2 C19 S1 49.21(8) . . ?
S2 C19 H191 127.5 . . ?
S1 C19 H191 109.5 . . ?
S2 C19 H192 60.3 . . ?
S1 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
S2 C19 H193 122.7 . . ?
S1 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?
S2 C19 H194 109.4 . . ?
S1 C19 H194 129.0 . . ?
H191 C19 H194 40.3 . . ?
H192 C19 H194 69.6 . . ?
H193 C19 H194 118.8 . . ?
S2 C19 H195 109.6 . . ?
S1 C19 H195 121.1 . . ?
H191 C19 H195 120.4 . . ?
H192 C19 H195 82.5 . . ?
H193 C19 H195 27.0 . . ?
H194 C19 H195 109.5 . . ?
S2 C19 H196 109.5 . . ?
S1 C19 H196 60.5 . . ?
H191 C19 H196 69.4 . . ?
H192 C19 H196 167.0 . . ?
H193 C19 H196 82.6 . . ?
H194 C19 H196 109.5 . . ?
H195 C19 H196 109.5 . . ?
C8 N1 C7 125.73(11) . . ?
C8 N1 C6 117.52(11) . . ?
C7 N1 C6 116.75(11) . . ?
C18 O3 H6 113(2) . . ?
C10 C11 C7 109.42(10) . . ?
C10 C11 C12 110.78(11) . . ?
C7 C11 C12 108.38(11) . . ?
C10 C11 C13 108.90(11) . . ?
C7 C11 C13 110.22(11) . . ?
C12 C11 C13 109.14(11) . . ?
C3 C1 C2 116.65(14) . . ?
C3 C1 C1 121.72(17) . 3_565 ?
C2 C1 C1 121.62(18) . 3_565 ?
C11 C10 C9 110.27(11) . . ?
C11 C10 H101 109.9(11) . . ?
C9 C10 H101 110.5(11) . . ?
C11 C10 H102 108.6(11) . . ?
C9 C10 H102 108.5(11) . . ?
H101 C10 H102 109.0(16) . . ?
O2 C7 N1 119.52(11) . . ?
O2 C7 C11 123.39(11) . . ?
N1 C7 C11 117.09(11) . . ?
C16 C13 C11 115.64(11) . . ?
C16 C13 H131 107.0(12) . . ?
C11 C13 H131 112.9(11) . . ?
C16 C13 H132 107.1(11) . . ?
C11 C13 H132 106.7(11) . . ?
H131 C13 H132 107.1(15) . . ?
C16 C15 C9 116.11(12) . . ?
C16 C15 H151 107.5(12) . . ?
C9 C15 H151 107.3(13) . . ?
C16 C15 H152 111.0(14) . . ?
C9 C15 H152 108.9(14) . . ?
H151 C15 H152 105.5(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C6 C4 119.67(14) . . ?
C5 C6 N1 120.86(13) . . ?
C4 C6 N1 119.46(13) . . ?
O1 C8 N1 119.32(13) . . ?
O1 C8 C9 123.48(14) . . ?
N1 C8 C9 117.19(12) . . ?
O4 C18 O3 123.30(15) . . ?
O4 C18 C16 124.12(15) . . ?
O3 C18 C16 112.45(14) . . ?
C8 C9 C14 108.15(13) . . ?
C8 C9 C10 109.06(12) . . ?
C14 C9 C10 110.59(13) . . ?
C8 C9 C15 110.62(12) . . ?
C14 C9 C15 109.23(13) . . ?
C10 C9 C15 109.19(12) . . ?
C15 C16 C18 110.91(13) . . ?
C15 C16 C13 110.30(12) . . ?
C18 C16 C13 113.23(12) . . ?
C15 C16 C17 109.29(14) . . ?
C18 C16 C17 104.08(13) . . ?
C13 C16 C17 108.78(14) . . ?
S1 O5 S2 54.17(8) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C3 C5 122.01(16) . . ?
C1 C3 H3 120.5(15) . . ?
C5 C3 H3 117.5(15) . . ?
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 . . ?
C1 C2 C4 121.90(17) . . ?
C1 C2 H2 121(2) . . ?
C4 C2 H2 117(2) . . ?
C6 C4 C2 119.85(17) . . ?
C6 C4 H4 119(2) . . ?
C2 C4 H4 121(2) . . ?
C6 C5 C3 119.86(16) . . ?
C6 C5 H5 118(2) . . ?
C3 C5 H5 122(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C20 S1 O5 53.26(10) . . . . ?
S2 C20 S1 C19 -54.24(12) . . . . ?
S1 C20 S2 O5 -50.86(9) . . . . ?
S1 C20 S2 C19 56.57(13) . . . . ?
O5 S2 C19 S1 50.63(10) . . . . ?
C20 S2 C19 S1 -54.67(12) . . . . ?
O5 S1 C19 S2 -51.75(12) . . . . ?
C20 S1 C19 S2 56.77(13) . . . . ?
C7 C11 C10 C9 -59.28(14) . . . . ?
C12 C11 C10 C9 -178.71(11) . . . . ?
C13 C11 C10 C9 61.25(14) . . . . ?
C8 N1 C7 O2 -176.42(14) . . . . ?
C6 N1 C7 O2 4.52(19) . . . . ?
C8 N1 C7 C11 3.5(2) . . . . ?
C6 N1 C7 C11 -175.54(11) . . . . ?
C10 C11 C7 O2 -152.84(13) . . . . ?
C12 C11 C7 O2 -31.94(18) . . . . ?
C13 C11 C7 O2 87.44(16) . . . . ?
C10 C11 C7 N1 27.22(15) . . . . ?
C12 C11 C7 N1 148.12(12) . . . . ?
C13 C11 C7 N1 -92.50(14) . . . . ?
C10 C11 C13 C16 -54.51(15) . . . . ?
C7 C11 C13 C16 65.53(15) . . . . ?
C12 C11 C13 C16 -175.56(12) . . . . ?
C8 N1 C6 C5 96.00(19) . . . . ?
C7 N1 C6 C5 -84.86(19) . . . . ?
C8 N1 C6 C4 -84.9(2) . . . . ?
C7 N1 C6 C4 94.26(19) . . . . ?
C7 N1 C8 O1 178.86(15) . . . . ?
C6 N1 C8 O1 -2.1(2) . . . . ?
C7 N1 C8 C9 -2.3(2) . . . . ?
C6 N1 C8 C9 176.78(13) . . . . ?
O1 C8 C9 C14 29.1(2) . . . . ?
N1 C8 C9 C14 -149.71(15) . . . . ?
O1 C8 C9 C10 149.43(17) . . . . ?
N1 C8 C9 C10 -29.39(18) . . . . ?
O1 C8 C9 C15 -90.5(2) . . . . ?
N1 C8 C9 C15 90.71(16) . . . . ?
C11 C10 C9 C8 60.42(15) . . . . ?
C11 C10 C9 C14 179.22(12) . . . . ?
C11 C10 C9 C15 -60.56(15) . . . . ?
C16 C15 C9 C8 -66.88(16) . . . . ?
C16 C15 C9 C14 174.19(13) . . . . ?
C16 C15 C9 C10 53.14(16) . . . . ?
C9 C15 C16 C18 81.52(16) . . . . ?
C9 C15 C16 C13 -44.75(17) . . . . ?
C9 C15 C16 C17 -164.29(14) . . . . ?
O4 C18 C16 C15 26.7(2) . . . . ?
O3 C18 C16 C15 -157.30(13) . . . . ?
O4 C18 C16 C13 151.34(15) . . . . ?
O3 C18 C16 C13 -32.68(17) . . . . ?
O4 C18 C16 C17 -90.69(19) . . . . ?
O3 C18 C16 C17 85.29(16) . . . . ?
C11 C13 C16 C15 45.38(16) . . . . ?
C11 C13 C16 C18 -79.57(16) . . . . ?
C11 C13 C16 C17 165.23(13) . . . . ?
C20 S1 O5 S2 -55.45(12) . . . . ?
C19 S1 O5 S2 51.54(13) . . . . ?
C19 S2 O5 S1 -53.89(11) . . . . ?
C20 S2 O5 S1 52.41(10) . . . . ?
C2 C1 C3 C5 1.2(3) . . . . ?
C1 C1 C3 C5 -179.8(2) 3_565 . . . ?
C3 C1 C2 C4 -1.9(4) . . . . ?
C1 C1 C2 C4 179.1(2) 3_565 . . . ?
C5 C6 C4 C2 1.4(3) . . . . ?
N1 C6 C4 C2 -177.7(2) . . . . ?
C1 C2 C4 C6 0.6(4) . . . . ?
C4 C6 C5 C3 -2.1(3) . . . . ?
N1 C6 C5 C3 177.00(17) . . . . ?
C1 C3 C5 C6 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.68
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.054


_database_code_depnum_ccdc_archive 'CCDC 927209'