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

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_exp_425
_audit_creation_date             2012-11-20
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H17 N2 S, C6 H4 N O5 S, H2 O'
_chemical_formula_sum            'C20 H23 N3 O6 S2'
_chemical_formula_weight         465.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O5S2
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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'

_cell_length_a                   7.5719(4)
_cell_length_b                   7.8718(4)
_cell_length_c                   9.8803(6)
_cell_angle_alpha                104.448(5)
_cell_angle_beta                 108.242(5)
_cell_angle_gamma                96.225(4)
_cell_volume                     530.37(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.2651
_cell_measurement_theta_min      2.8868
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3739
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9877
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   69.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7753  178.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega   72.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7753  178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566   19.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -92.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  178.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  -99.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega  -93.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  -19.0000   30.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0579319000
_diffrn_orient_matrix_UB_12      -0.0619317000
_diffrn_orient_matrix_UB_13      0.0181835000
_diffrn_orient_matrix_UB_21      0.0161700000
_diffrn_orient_matrix_UB_22      0.0389528000
_diffrn_orient_matrix_UB_23      0.0768564000
_diffrn_orient_matrix_UB_31      -0.0807971000
_diffrn_orient_matrix_UB_32      -0.0606355000
_diffrn_orient_matrix_UB_33      -0.0064808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2554
_reflns_number_total             2616
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.1354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0687
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2512(4) -0.3994(4) 0.7792(3) 0.0219(7) Uani 1 1 d . . .
H1A H -0.3499 -0.3666 0.7081 0.033 Uiso 1 1 calc R . .
H1B H -0.2677 -0.3689 0.8742 0.033 Uiso 1 1 calc R . .
H1C H -0.2574 -0.5260 0.7451 0.033 Uiso 1 1 calc R . .
C2 C 0.0807(4) -0.2561(3) 0.9268(3) 0.0176(6) Uani 1 1 d . . .
H2 H 0.0618 -0.2844 1.0079 0.021 Uiso 1 1 calc R . .
C3 C 0.2540(4) -0.1693(3) 0.9424(3) 0.0195(6) Uani 1 1 d . . .
H3 H 0.3520 -0.1389 1.0344 0.023 Uiso 1 1 calc R . .
C4 C 0.2891(4) -0.1241(3) 0.8228(3) 0.0182(6) Uani 1 1 d . . .
C5 C 0.1332(4) -0.1721(3) 0.6886(3) 0.0202(6) Uani 1 1 d . . .
H5 H 0.1476 -0.1444 0.6060 0.024 Uiso 1 1 calc R . .
C6 C -0.0391(4) -0.2585(3) 0.6775(3) 0.0194(6) Uani 1 1 d . . .
H6 H -0.1407 -0.2880 0.5877 0.023 Uiso 1 1 calc R . .
C7 C 0.4773(4) -0.0351(3) 0.8440(3) 0.0222(6) Uani 1 1 d . . .
H7 H 0.5673 0.0008 0.9401 0.027 Uiso 1 1 calc R . .
C8 C 0.5317(4) -0.0002(3) 0.7346(3) 0.0200(6) Uani 1 1 d . . .
H8 H 0.4404 -0.0400 0.6390 0.024 Uiso 1 1 calc R . .
C9 C 0.7127(4) 0.0904(3) 0.7483(3) 0.0198(6) Uani 1 1 d . . .
C10 C 0.7658(4) 0.1210(3) 0.6346(3) 0.0202(6) Uani 1 1 d . . .
H10 H 0.6847 0.0817 0.5353 0.024 Uiso 1 1 calc R . .
C11 C 0.9510(4) 0.2157(3) 0.6799(3) 0.0188(6) Uani 1 1 d . . .
H11 H 1.0053 0.2457 0.6144 0.023 Uiso 1 1 calc R . .
C12 C 1.0455(4) 0.2603(3) 0.8315(3) 0.0166(6) Uani 1 1 d . . .
C13 C 1.3058(4) 0.3826(4) 1.0713(3) 0.0302(7) Uani 1 1 d . . .
H13A H 1.2203 0.4285 1.1184 0.045 Uiso 1 1 calc R . .
H13B H 1.4247 0.4667 1.1122 0.045 Uiso 1 1 calc R . .
H13C H 1.3263 0.2706 1.0889 0.045 Uiso 1 1 calc R . .
C14 C 1.3434(4) 0.4055(4) 0.8319(4) 0.0255(7) Uani 1 1 d . . .
H14A H 1.3745 0.3001 0.7788 0.038 Uiso 1 1 calc R . .
H14B H 1.4580 0.4864 0.9019 0.038 Uiso 1 1 calc R . .
H14C H 1.2763 0.4629 0.7623 0.038 Uiso 1 1 calc R . .
C15 C 0.9057(4) 0.0357(3) 0.2889(3) 0.0148(5) Uani 1 1 d . . .
C16 C 1.0944(4) 0.1181(3) 0.3354(3) 0.0153(5) Uani 1 1 d . . .
H16 H 1.1901 0.0526 0.3407 0.018 Uiso 1 1 calc R . .
C17 C 1.1336(4) 0.3047(3) 0.3739(3) 0.0161(5) Uani 1 1 d . . .
C18 C 0.9976(4) 0.4069(3) 0.3659(3) 0.0183(6) Uani 1 1 d . . .
H18 H 1.0300 0.5310 0.3909 0.022 Uiso 1 1 calc R . .
C19 C 0.8090(4) 0.3192(3) 0.3190(3) 0.0182(6) Uani 1 1 d . . .
H19 H 0.7134 0.3850 0.3128 0.022 Uiso 1 1 calc R . .
C20 C 0.7641(4) 0.1351(3) 0.2819(3) 0.0164(5) Uani 1 1 d . . .
H20 H 0.6384 0.0771 0.2520 0.020 Uiso 1 1 calc R . .
N1 N -0.0648(3) -0.3020(3) 0.7947(3) 0.0166(5) Uani 1 1 d . . .
N2 N 1.2243(3) 0.3554(3) 0.9118(3) 0.0236(5) Uani 1 1 d . . .
N3 N 1.3345(3) 0.3974(3) 0.4274(3) 0.0215(5) Uani 1 1 d . . .
O1 O 0.6927(3) -0.2538(2) 0.0918(2) 0.0245(5) Uani 1 1 d . . .
O2 O 0.7726(3) -0.2423(2) 0.3509(2) 0.0198(4) Uani 1 1 d . . .
O3 O 1.0130(3) -0.2675(2) 0.2366(2) 0.0205(4) Uani 1 1 d . . .
O4 O 1.4551(3) 0.3075(3) 0.4299(3) 0.0401(6) Uani 1 1 d . . .
O5 O 1.3700(3) 0.5608(3) 0.4651(3) 0.0353(6) Uani 1 1 d . . .
O6 O 0.4095(3) 0.8567(3) 0.3095(3) 0.0272(5) Uani 1 1 d . . .
S1 S 0.90140(9) 0.18130(8) 0.91949(7) 0.02088(17) Uani 1 1 d . . .
S2 S 0.84063(7) -0.20341(7) 0.23706(6) 0.01407(15) Uani 1 1 d . . .
H6A H 0.309(5) 0.789(4) 0.305(4) 0.027(8) Uiso 1 1 d . . .
H6B H 0.510(9) 0.811(9) 0.313(8) 0.13(2) Uiso 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
C1 0.0154(15) 0.0265(14) 0.0217(16) 0.0040(12) 0.0068(13) 0.0019(12)
C2 0.0198(14) 0.0179(12) 0.0154(14) 0.0050(11) 0.0061(12) 0.0058(11)
C3 0.0175(14) 0.0201(13) 0.0195(15) 0.0063(11) 0.0037(12) 0.0064(11)
C4 0.0185(14) 0.0120(11) 0.0249(15) 0.0061(11) 0.0077(12) 0.0058(11)
C5 0.0277(16) 0.0192(13) 0.0201(15) 0.0089(12) 0.0134(13) 0.0089(12)
C6 0.0215(15) 0.0200(12) 0.0134(14) 0.0031(11) 0.0024(12) 0.0066(11)
C7 0.0209(15) 0.0222(13) 0.0207(15) 0.0056(12) 0.0034(12) 0.0066(12)
C8 0.0217(15) 0.0168(12) 0.0202(16) 0.0047(11) 0.0061(12) 0.0050(11)
C9 0.0190(14) 0.0154(12) 0.0238(16) 0.0048(11) 0.0062(12) 0.0048(11)
C10 0.0235(14) 0.0180(12) 0.0175(15) 0.0043(11) 0.0057(12) 0.0048(11)
C11 0.0221(14) 0.0192(13) 0.0183(15) 0.0068(11) 0.0101(12) 0.0056(11)
C12 0.0203(15) 0.0141(12) 0.0175(15) 0.0031(11) 0.0105(12) 0.0045(11)
C13 0.0282(17) 0.0317(16) 0.0234(17) 0.0077(13) 0.0021(13) -0.0003(14)
C14 0.0205(15) 0.0251(14) 0.0310(17) 0.0071(12) 0.0121(13) -0.0001(12)
C15 0.0183(14) 0.0154(11) 0.0110(13) 0.0050(10) 0.0051(11) 0.0020(11)
C16 0.0162(13) 0.0190(12) 0.0134(14) 0.0080(10) 0.0060(11) 0.0052(10)
C17 0.0174(13) 0.0179(11) 0.0128(13) 0.0046(10) 0.0062(11) 0.0005(10)
C18 0.0214(16) 0.0149(12) 0.0195(16) 0.0069(11) 0.0072(13) 0.0031(11)
C19 0.0202(15) 0.0208(13) 0.0177(15) 0.0095(12) 0.0072(12) 0.0099(12)
C20 0.0127(13) 0.0225(13) 0.0132(14) 0.0070(11) 0.0030(11) 0.0006(11)
N1 0.0163(12) 0.0183(11) 0.0143(12) 0.0036(9) 0.0048(10) 0.0044(9)
N2 0.0190(12) 0.0291(12) 0.0193(13) 0.0065(10) 0.0050(10) -0.0014(10)
N3 0.0190(12) 0.0237(12) 0.0214(13) 0.0085(10) 0.0063(10) 0.0009(10)
O1 0.0275(11) 0.0203(9) 0.0198(11) 0.0044(8) 0.0022(9) 0.0032(8)
O2 0.0203(11) 0.0204(9) 0.0240(12) 0.0113(8) 0.0109(9) 0.0054(8)
O3 0.0200(10) 0.0170(9) 0.0306(12) 0.0093(8) 0.0146(9) 0.0059(7)
O4 0.0187(11) 0.0321(11) 0.0612(17) 0.0008(11) 0.0135(12) 0.0039(10)
O5 0.0254(12) 0.0211(10) 0.0487(15) 0.0137(10) -0.0003(10) -0.0051(9)
O6 0.0208(11) 0.0240(10) 0.0400(14) 0.0119(9) 0.0129(10) 0.0054(9)
S1 0.0214(4) 0.0238(3) 0.0181(4) 0.0077(3) 0.0078(3) 0.0016(3)
S2 0.0151(3) 0.0128(3) 0.0149(3) 0.0048(2) 0.0056(3) 0.0030(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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N1 1.475(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(4) . ?
C2 N1 1.351(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(4) . ?
C4 C5 1.403(4) . ?
C4 C7 1.445(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(4) . ?
C6 H6 0.9300 . ?
C6 N1 1.349(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.347(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.425(4) . ?
C9 C10 1.371(4) . ?
C9 S1 1.754(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 N2 1.354(3) . ?
C12 S1 1.746(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 N2 1.451(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 N2 1.454(3) . ?
C15 C16 1.383(4) . ?
C15 C20 1.389(4) . ?
C15 S2 1.791(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.395(3) . ?
C17 C18 1.370(4) . ?
C17 N3 1.480(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
N3 O4 1.212(3) . ?
N3 O5 1.220(3) . ?
O1 S2 1.444(2) . ?
O2 S2 1.4571(19) . ?
O3 S2 1.4504(19) . ?
O6 H6A 0.86(3) . ?
O6 H6B 0.87(7) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
C3 C2 H2 119.7 . . ?
N1 C2 H2 119.7 . . ?
N1 C2 C3 120.7(3) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C7 119.6(3) . . ?
C5 C4 C3 115.7(2) . . ?
C5 C4 C7 124.8(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.4 . . ?
N1 C6 C5 121.1(3) . . ?
N1 C6 H6 119.4 . . ?
C4 C7 H7 117.6 . . ?
C8 C7 C4 124.7(3) . . ?
C8 C7 H7 117.6 . . ?
C7 C8 H8 116.2 . . ?
C7 C8 C9 127.6(3) . . ?
C9 C8 H8 116.2 . . ?
C8 C9 S1 123.2(2) . . ?
C10 C9 C8 126.5(3) . . ?
C10 C9 S1 110.3(2) . . ?
C9 C10 H10 122.8 . . ?
C9 C10 C11 114.5(3) . . ?
C11 C10 H10 122.8 . . ?
C10 C11 H11 123.5 . . ?
C12 C11 C10 113.0(2) . . ?
C12 C11 H11 123.5 . . ?
C11 C12 S1 111.17(19) . . ?
N2 C12 C11 128.0(2) . . ?
N2 C12 S1 120.8(2) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
C16 C15 C20 121.2(2) . . ?
C16 C15 S2 119.9(2) . . ?
C20 C15 S2 118.90(18) . . ?
C15 C16 H16 121.7 . . ?
C15 C16 C17 116.5(2) . . ?
C17 C16 H16 121.7 . . ?
C16 C17 N3 117.9(2) . . ?
C18 C17 C16 123.9(2) . . ?
C18 C17 N3 118.2(2) . . ?
C17 C18 H18 121.0 . . ?
C17 C18 C19 117.9(2) . . ?
C19 C18 H18 121.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C2 N1 C1 119.9(2) . . ?
C6 N1 C1 120.2(2) . . ?
C6 N1 C2 119.9(2) . . ?
C12 N2 C13 120.8(2) . . ?
C12 N2 C14 118.5(2) . . ?
C13 N2 C14 120.0(2) . . ?
O4 N3 C17 118.5(2) . . ?
O4 N3 O5 123.4(2) . . ?
O5 N3 C17 118.1(2) . . ?
H6A O6 H6B 118(4) . . ?
C12 S1 C9 91.05(13) . . ?
O1 S2 C15 104.74(12) . . ?
O1 S2 O2 112.67(11) . . ?
O1 S2 O3 114.16(11) . . ?
O2 S2 C15 105.82(11) . . ?
O3 S2 C15 105.41(11) . . ?
O3 S2 O2 113.02(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6A O3 0.86(3) 2.09(4) 2.854(3) 147(3) 1_465
O6 H6A O5 0.86(3) 2.66(3) 3.131(3) 116(3) 1_455
O6 H6B O2 0.87(7) 2.01(7) 2.873(3) 168(6) 1_565

_database_code_depnum_ccdc_archive 'CCDC 962681'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sa2409

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N2 S, C8 H9 O3 S'
_chemical_formula_sum            'C22 H26 N2 O3 S2'
_chemical_formula_weight         430.57

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

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

_cell_length_a                   8.765(3)
_cell_length_b                   10.240(4)
_cell_length_c                   12.354(5)
_cell_angle_alpha                103.590(5)
_cell_angle_beta                 104.227(6)
_cell_angle_gamma                91.636(4)
_cell_volume                     1040.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3773
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7044
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9123
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4707
_reflns_number_gt                4380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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^)+(0.0568P)^2^+0.7536P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4707
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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 0.48505(7) 0.75225(6) 0.65232(5) 0.02865(15) Uani 1 1 d . . .
S2 S 1.09069(6) 0.31670(5) 0.78279(5) 0.02385(15) Uani 1 1 d . . .
O1 O 1.1000(2) 0.37105(17) 0.68608(15) 0.0341(4) Uani 1 1 d . . .
O2 O 1.16962(18) 0.19375(17) 0.78425(16) 0.0361(4) Uani 1 1 d . . .
O3 O 1.13804(19) 0.41737(17) 0.89286(14) 0.0329(4) Uani 1 1 d . . .
N1 N 0.7318(2) 0.6559(2) 0.57568(18) 0.0327(4) Uani 1 1 d . . .
N2 N -0.2016(2) 0.87291(19) 0.91636(16) 0.0266(4) Uani 1 1 d . . .
C1 C 0.7406(3) 0.7754(3) 0.5319(2) 0.0380(6) Uani 1 1 d . . .
H1A H 0.7735 0.8554 0.5967 0.057 Uiso 1 1 calc R . .
H1B H 0.6366 0.7850 0.4838 0.057 Uiso 1 1 calc R . .
H1C H 0.8178 0.7662 0.4856 0.057 Uiso 1 1 calc R . .
C2 C 0.8421(3) 0.5553(3) 0.5549(2) 0.0355(5) Uani 1 1 d . . .
H2A H 0.9095 0.5836 0.5104 0.053 Uiso 1 1 calc R . .
H2B H 0.7831 0.4683 0.5116 0.053 Uiso 1 1 calc R . .
H2C H 0.9081 0.5462 0.6289 0.053 Uiso 1 1 calc R . .
C3 C 0.6204(3) 0.6353(2) 0.62704(18) 0.0278(5) Uani 1 1 d . . .
C4 C 0.5934(3) 0.5213(2) 0.6673(2) 0.0325(5) Uani 1 1 d . . .
H4 H 0.6553 0.4465 0.6621 0.039 Uiso 1 1 calc R . .
C5 C 0.4662(3) 0.5312(2) 0.7155(2) 0.0340(5) Uani 1 1 d . . .
H5 H 0.4318 0.4617 0.7455 0.041 Uiso 1 1 calc R . .
C6 C 0.3925(3) 0.6491(2) 0.71693(19) 0.0287(5) Uani 1 1 d . . .
C7 C 0.2610(3) 0.6814(2) 0.76134(19) 0.0281(4) Uani 1 1 d . . .
H7 H 0.2200 0.6144 0.7910 0.034 Uiso 1 1 calc R . .
C8 C 0.1851(3) 0.7955(2) 0.76746(19) 0.0282(5) Uani 1 1 d . . .
H8 H 0.2212 0.8645 0.7375 0.034 Uiso 1 1 calc R . .
C9 C 0.0521(3) 0.8174(2) 0.81726(18) 0.0256(4) Uani 1 1 d . . .
C10 C -0.0120(3) 0.7243(2) 0.86619(19) 0.0279(5) Uani 1 1 d . . .
H10 H 0.0313 0.6403 0.8656 0.034 Uiso 1 1 calc R . .
C11 C -0.1356(3) 0.7537(2) 0.91431(19) 0.0298(5) Uani 1 1 d . . .
H11 H -0.1764 0.6897 0.9470 0.036 Uiso 1 1 calc R . .
C12 C -0.1437(3) 0.9635(2) 0.86863(19) 0.0278(4) Uani 1 1 d . . .
H12 H -0.1906 1.0460 0.8687 0.033 Uiso 1 1 calc R . .
C13 C -0.0200(3) 0.9387(2) 0.82066(19) 0.0269(4) Uani 1 1 d . . .
H13 H 0.0184 1.0047 0.7888 0.032 Uiso 1 1 calc R . .
C14 C -0.3333(3) 0.9021(3) 0.9692(2) 0.0358(5) Uani 1 1 d . . .
H14A H -0.4310 0.8528 0.9164 0.054 Uiso 1 1 calc R . .
H14B H -0.3447 0.9992 0.9849 0.054 Uiso 1 1 calc R . .
H14C H -0.3122 0.8739 1.0416 0.054 Uiso 1 1 calc R . .
C15 C 0.8858(2) 0.2672(2) 0.76169(17) 0.0210(4) Uani 1 1 d . . .
C16 C 0.7985(2) 0.1775(2) 0.65890(18) 0.0241(4) Uani 1 1 d . . .
C17 C 0.6412(3) 0.1407(2) 0.65184(19) 0.0276(5) Uani 1 1 d . . .
H17 H 0.5794 0.0800 0.5835 0.033 Uiso 1 1 calc R . .
C18 C 0.5717(2) 0.1896(2) 0.74123(19) 0.0264(4) Uani 1 1 d . . .
H18 H 0.4648 0.1606 0.7336 0.032 Uiso 1 1 calc R . .
C19 C 0.6572(2) 0.2804(2) 0.84155(18) 0.0229(4) Uani 1 1 d . . .
C20 C 0.8155(2) 0.3183(2) 0.85066(17) 0.0216(4) Uani 1 1 d . . .
H20 H 0.8762 0.3801 0.9188 0.026 Uiso 1 1 calc R . .
C21 C 0.8662(3) 0.1238(3) 0.5577(2) 0.0336(5) Uani 1 1 d . . .
H21A H 0.8864 0.1976 0.5234 0.050 Uiso 1 1 calc R . .
H21B H 0.7907 0.0539 0.4999 0.050 Uiso 1 1 calc R . .
H21C H 0.9654 0.0852 0.5840 0.050 Uiso 1 1 calc R . .
C22 C 0.5839(3) 0.3359(3) 0.9393(2) 0.0338(5) Uani 1 1 d . . .
H22A H 0.4690 0.3315 0.9093 0.051 Uiso 1 1 calc R . .
H22B H 0.6261 0.4299 0.9758 0.051 Uiso 1 1 calc R . .
H22C H 0.6090 0.2822 0.9964 0.051 Uiso 1 1 calc R . .

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
S1 0.0289(3) 0.0298(3) 0.0311(3) 0.0106(2) 0.0114(2) 0.0079(2)
S2 0.0197(2) 0.0245(3) 0.0304(3) 0.0107(2) 0.0086(2) 0.00003(19)
O1 0.0362(9) 0.0368(9) 0.0370(9) 0.0173(7) 0.0165(7) -0.0012(7)
O2 0.0215(8) 0.0316(9) 0.0599(11) 0.0182(8) 0.0127(7) 0.0063(7)
O3 0.0260(8) 0.0352(9) 0.0341(9) 0.0052(7) 0.0059(7) -0.0075(7)
N1 0.0306(10) 0.0370(11) 0.0364(11) 0.0132(9) 0.0148(8) 0.0129(9)
N2 0.0237(9) 0.0314(10) 0.0253(9) 0.0080(7) 0.0068(7) 0.0014(7)
C1 0.0406(13) 0.0412(14) 0.0419(14) 0.0191(11) 0.0192(11) 0.0120(11)
C2 0.0320(12) 0.0403(13) 0.0367(13) 0.0097(10) 0.0122(10) 0.0127(10)
C3 0.0249(10) 0.0340(11) 0.0235(10) 0.0071(9) 0.0039(8) 0.0058(9)
C4 0.0330(12) 0.0307(11) 0.0364(12) 0.0115(10) 0.0103(10) 0.0076(9)
C5 0.0337(12) 0.0330(12) 0.0362(12) 0.0115(10) 0.0081(10) 0.0050(10)
C6 0.0289(11) 0.0302(11) 0.0260(11) 0.0064(9) 0.0062(9) 0.0008(9)
C7 0.0267(10) 0.0315(11) 0.0246(10) 0.0059(9) 0.0053(8) -0.0004(9)
C8 0.0300(11) 0.0303(11) 0.0253(10) 0.0094(9) 0.0068(9) -0.0001(9)
C9 0.0249(10) 0.0293(11) 0.0201(9) 0.0048(8) 0.0029(8) 0.0014(8)
C10 0.0326(11) 0.0234(10) 0.0277(11) 0.0073(8) 0.0065(9) 0.0037(9)
C11 0.0340(12) 0.0287(11) 0.0273(11) 0.0107(9) 0.0065(9) -0.0028(9)
C12 0.0282(11) 0.0265(10) 0.0294(11) 0.0093(9) 0.0063(9) 0.0035(9)
C13 0.0271(10) 0.0261(10) 0.0287(11) 0.0099(8) 0.0070(8) 0.0001(8)
C14 0.0292(11) 0.0460(14) 0.0339(12) 0.0074(10) 0.0137(10) 0.0025(10)
C15 0.0198(9) 0.0211(9) 0.0241(10) 0.0093(8) 0.0057(7) 0.0027(7)
C16 0.0247(10) 0.0237(10) 0.0256(10) 0.0077(8) 0.0076(8) 0.0057(8)
C17 0.0232(10) 0.0260(10) 0.0275(11) 0.0006(8) 0.0015(8) 0.0003(8)
C18 0.0178(9) 0.0299(11) 0.0309(11) 0.0085(9) 0.0042(8) 0.0010(8)
C19 0.0215(9) 0.0248(10) 0.0246(10) 0.0088(8) 0.0069(8) 0.0046(8)
C20 0.0205(9) 0.0223(9) 0.0222(9) 0.0077(8) 0.0040(7) 0.0007(8)
C21 0.0342(12) 0.0364(12) 0.0289(11) 0.0001(9) 0.0130(9) 0.0045(10)
C22 0.0257(11) 0.0460(14) 0.0302(12) 0.0060(10) 0.0117(9) -0.0003(10)

_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 C3 1.739(2) . ?
S1 C6 1.754(2) . ?
S2 O1 1.4497(17) . ?
S2 O2 1.4555(17) . ?
S2 O3 1.4572(18) . ?
S2 C15 1.790(2) . ?
N1 C3 1.326(3) . ?
N1 C2 1.455(3) . ?
N1 C1 1.457(3) . ?
N2 C12 1.357(3) . ?
N2 C11 1.363(3) . ?
N2 C14 1.465(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.408(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(3) . ?
C7 C8 1.357(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.446(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.406(3) . ?
C9 C10 1.413(3) . ?
C10 C11 1.367(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.361(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.393(3) . ?
C15 C16 1.406(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.510(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(3) . ?
C19 C22 1.508(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C3 S1 C6 91.62(11) . . ?
O1 S2 O2 113.07(11) . . ?
O1 S2 O3 112.83(11) . . ?
O2 S2 O3 112.95(11) . . ?
O1 S2 C15 106.05(10) . . ?
O2 S2 C15 105.28(10) . . ?
O3 S2 C15 105.82(10) . . ?
C3 N1 C2 120.7(2) . . ?
C3 N1 C1 120.9(2) . . ?
C2 N1 C1 118.2(2) . . ?
C12 N2 C11 119.04(19) . . ?
C12 N2 C14 120.7(2) . . ?
C11 N2 C14 120.2(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 126.6(2) . . ?
N1 C3 S1 122.19(18) . . ?
C4 C3 S1 111.20(17) . . ?
C5 C4 C3 111.9(2) . . ?
C5 C4 H4 124.0 . . ?
C3 C4 H4 124.0 . . ?
C4 C5 C6 115.5(2) . . ?
C4 C5 H5 122.2 . . ?
C6 C5 H5 122.2 . . ?
C5 C6 C7 125.6(2) . . ?
C5 C6 S1 109.72(18) . . ?
C7 C6 S1 124.64(18) . . ?
C8 C7 C6 128.7(2) . . ?
C8 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
C7 C8 C9 123.3(2) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C13 C9 C10 115.9(2) . . ?
C13 C9 C8 119.9(2) . . ?
C10 C9 C8 124.2(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C10 121.4(2) . . ?
N2 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
N2 C12 C13 121.5(2) . . ?
N2 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C9 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C9 C13 H13 119.3 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.76(19) . . ?
C20 C15 S2 118.25(15) . . ?
C16 C15 S2 120.98(16) . . ?
C17 C16 C15 116.99(19) . . ?
C17 C16 C21 119.9(2) . . ?
C15 C16 C21 123.09(19) . . ?
C18 C17 C16 122.4(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 118.09(19) . . ?
C18 C19 C22 121.45(19) . . ?
C20 C19 C22 120.45(19) . . ?
C15 C20 C19 121.29(19) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C2 N1 C3 C4 0.3(4) . . . . ?
C1 N1 C3 C4 176.3(2) . . . . ?
C2 N1 C3 S1 -179.42(17) . . . . ?
C1 N1 C3 S1 -3.5(3) . . . . ?
C6 S1 C3 N1 179.9(2) . . . . ?
C6 S1 C3 C4 0.08(18) . . . . ?
N1 C3 C4 C5 -179.3(2) . . . . ?
S1 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C4 C5 C6 S1 1.1(3) . . . . ?
C3 S1 C6 C5 -0.63(18) . . . . ?
C3 S1 C6 C7 -179.5(2) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
S1 C6 C7 C8 -2.6(4) . . . . ?
C6 C7 C8 C9 -178.9(2) . . . . ?
C7 C8 C9 C13 179.8(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C13 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 178.3(2) . . . . ?
C12 N2 C11 C10 0.6(3) . . . . ?
C14 N2 C11 C10 -179.6(2) . . . . ?
C9 C10 C11 N2 0.3(3) . . . . ?
C11 N2 C12 C13 -1.1(3) . . . . ?
C14 N2 C12 C13 179.1(2) . . . . ?
N2 C12 C13 C9 0.7(3) . . . . ?
C10 C9 C13 C12 0.1(3) . . . . ?
C8 C9 C13 C12 -178.9(2) . . . . ?
O1 S2 C15 C20 -125.74(17) . . . . ?
O2 S2 C15 C20 114.17(17) . . . . ?
O3 S2 C15 C20 -5.66(18) . . . . ?
O1 S2 C15 C16 55.29(19) . . . . ?
O2 S2 C15 C16 -64.80(19) . . . . ?
O3 S2 C15 C16 175.36(16) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
S2 C15 C16 C17 177.63(16) . . . . ?
C20 C15 C16 C21 177.2(2) . . . . ?
S2 C15 C16 C21 -3.9(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C21 C16 C17 C18 -178.4(2) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C17 C18 C19 C22 179.4(2) . . . . ?
C16 C15 C20 C19 1.1(3) . . . . ?
S2 C15 C20 C19 -177.85(15) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C22 C19 C20 C15 179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 962701'