# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Li, Liang'
'Cui, Huijuan'
'Yang, Zhou'
'Tao, Xutang'
'Lin, Xinsong'
'Ye, Ning'
'Yang, Huai'

_publ_contact_author_name        'Yang, Zhou'
_publ_contact_author_email       yangz@ustb.edu.cn

_publ_section_title              
;
Synthesis and characterization of thienyl-substituted
pyridinium salts for second-order nonlinear optics
;

# Attachment '- 3a.cif'

data_shelx(3a)
_database_code_depnum_ccdc_archive 'CCDC 843803'
#TrackingRef '- 3a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 I N2 S'
_chemical_formula_weight         372.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   10.1143(5)
_cell_length_b                   20.9362(13)
_cell_length_c                   14.6323(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1530(10)
_cell_angle_gamma                90.00
_cell_volume                     3004.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    10677
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_T_max  0.7735
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            27779
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.87
_reflns_number_total             7144
_reflns_number_gt                5874
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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^)+(0.0140P)^2^+0.0000P] 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         7144
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0467
_refine_ls_wR_factor_gt          0.0452
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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
I1 I 0.040205(15) 0.253346(6) 0.003141(9) 0.02547(4) Uani 1 1 d . . .
I2 I 0.418952(13) 0.496264(6) 0.252223(9) 0.02270(4) Uani 1 1 d . . .
S1 S 0.43732(5) 0.33334(2) 0.88140(3) 0.01880(11) Uani 1 1 d . . .
S2 S 1.01982(5) 0.43901(2) 0.37178(3) 0.01777(11) Uani 1 1 d . . .
N1 N 1.18095(17) 0.53206(7) 0.46202(11) 0.0197(4) Uani 1 1 d . . .
N2 N 0.48966(17) 0.20872(7) 0.14612(11) 0.0180(4) Uani 1 1 d . . .
N3 N 0.27081(17) 0.24181(7) 0.78829(12) 0.0193(4) Uani 1 1 d . . .
N4 N 0.98656(16) 0.55196(7) 1.12106(11) 0.0163(3) Uani 1 1 d . . .
C1 C 0.1629(2) 0.28944(9) 0.76935(14) 0.0241(5) Uani 1 1 d . . .
H1A H 0.1173 0.2899 0.8212 0.036 Uiso 1 1 calc R . .
H1B H 0.0965 0.2789 0.7104 0.036 Uiso 1 1 calc R . .
H1C H 0.2021 0.3316 0.7637 0.036 Uiso 1 1 calc R . .
C2 C 0.2259(2) 0.17538(9) 0.77479(15) 0.0294(5) Uani 1 1 d . . .
H2A H 0.3019 0.1486 0.7669 0.044 Uiso 1 1 calc R . .
H2B H 0.1504 0.1721 0.7184 0.044 Uiso 1 1 calc R . .
H2C H 0.1954 0.1609 0.8299 0.044 Uiso 1 1 calc R . .
C3 C 0.3908(2) 0.25421(8) 0.84908(13) 0.0173(4) Uani 1 1 d . . .
C4 C 0.4959(2) 0.21254(9) 0.88908(14) 0.0207(4) Uani 1 1 d . . .
H4 H 0.4902 0.1675 0.8814 0.025 Uiso 1 1 calc R . .
C5 C 0.6108(2) 0.24413(8) 0.94170(13) 0.0202(4) Uani 1 1 d . . .
H5 H 0.6915 0.2221 0.9726 0.024 Uiso 1 1 calc R . .
C6 C 0.5991(2) 0.30950(9) 0.94578(13) 0.0181(4) Uani 1 1 d . . .
C7 C 0.6985(2) 0.35371(9) 0.99267(13) 0.0190(4) Uani 1 1 d . . .
H7 H 0.7829 0.3365 1.0272 0.023 Uiso 1 1 calc R . .
C8 C 0.6855(2) 0.41828(8) 0.99341(13) 0.0186(4) Uani 1 1 d . . .
H8 H 0.6000 0.4358 0.9617 0.022 Uiso 1 1 calc R . .
C9 C 0.7898(2) 0.46183(9) 1.03788(13) 0.0172(4) Uani 1 1 d . . .
C10 C 0.7644(2) 0.52834(9) 1.03030(13) 0.0203(4) Uani 1 1 d . . .
H10 H 0.6778 0.5433 0.9960 0.024 Uiso 1 1 calc R . .
C11 C 0.8623(2) 0.57130(9) 1.07140(13) 0.0196(4) Uani 1 1 d . . .
H11 H 0.8428 0.6157 1.0650 0.024 Uiso 1 1 calc R . .
C12 C 0.9212(2) 0.44380(9) 1.08863(13) 0.0183(4) Uani 1 1 d . . .
H12 H 0.9444 0.3998 1.0949 0.022 Uiso 1 1 calc R . .
C13 C 1.0162(2) 0.48838(9) 1.12911(13) 0.0187(4) Uani 1 1 d . . .
H13 H 1.1040 0.4749 1.1633 0.022 Uiso 1 1 calc R . .
C14 C 1.0892(2) 0.59900(8) 1.16666(14) 0.0205(4) Uani 1 1 d . . .
H14A H 1.0829 0.6368 1.1263 0.031 Uiso 1 1 calc R . .
H14B H 1.1803 0.5802 1.1766 0.031 Uiso 1 1 calc R . .
H14C H 1.0728 0.6114 1.2275 0.031 Uiso 1 1 calc R . .
C15 C 1.2856(2) 0.48317(9) 0.49030(14) 0.0245(5) Uani 1 1 d . . .
H15A H 1.2441 0.4440 0.5071 0.037 Uiso 1 1 calc R . .
H15B H 1.3554 0.4983 0.5449 0.037 Uiso 1 1 calc R . .
H15C H 1.3276 0.4744 0.4379 0.037 Uiso 1 1 calc R . .
C16 C 1.2223(2) 0.59847(8) 0.48067(14) 0.0252(5) Uani 1 1 d . . .
H16A H 1.2507 0.6160 0.4263 0.038 Uiso 1 1 calc R . .
H16B H 1.2987 0.6007 0.5367 0.038 Uiso 1 1 calc R . .
H16C H 1.1455 0.6233 0.4915 0.038 Uiso 1 1 calc R . .
C17 C 1.0600(2) 0.51808(8) 0.40435(13) 0.0158(4) Uani 1 1 d . . .
C18 C 0.9513(2) 0.55877(9) 0.36498(13) 0.0182(4) Uani 1 1 d . . .
H18 H 0.9538 0.6038 0.3737 0.022 Uiso 1 1 calc R . .
C19 C 0.8389(2) 0.52580(8) 0.31141(13) 0.0174(4) Uani 1 1 d . . .
H19 H 0.7569 0.5467 0.2801 0.021 Uiso 1 1 calc R . .
C20 C 0.8562(2) 0.46020(9) 0.30736(13) 0.0162(4) Uani 1 1 d . . .
C21 C 0.7609(2) 0.41399(8) 0.26235(13) 0.0179(4) Uani 1 1 d . . .
H21 H 0.6758 0.4293 0.2260 0.021 Uiso 1 1 calc R . .
C22 C 0.7792(2) 0.34961(9) 0.26598(13) 0.0187(4) Uani 1 1 d . . .
H22 H 0.8655 0.3340 0.2997 0.022 Uiso 1 1 calc R . .
C23 C 0.6784(2) 0.30357(9) 0.22288(13) 0.0168(4) Uani 1 1 d . . .
C24 C 0.7080(2) 0.23764(9) 0.23713(14) 0.0209(4) Uani 1 1 d . . .
H24 H 0.7951 0.2248 0.2736 0.025 Uiso 1 1 calc R . .
C25 C 0.6138(2) 0.19227(9) 0.19951(14) 0.0210(4) Uani 1 1 d . . .
H25 H 0.6357 0.1484 0.2110 0.025 Uiso 1 1 calc R . .
C26 C 0.5469(2) 0.31841(9) 0.16788(13) 0.0178(4) Uani 1 1 d . . .
H26 H 0.5209 0.3618 0.1564 0.021 Uiso 1 1 calc R . .
C27 C 0.4565(2) 0.27111(9) 0.13095(13) 0.0188(4) Uani 1 1 d . . .
H27 H 0.3686 0.2822 0.0939 0.023 Uiso 1 1 calc R . .
C28 C 0.3916(2) 0.15868(9) 0.10374(14) 0.0240(5) Uani 1 1 d . . .
H28A H 0.2986 0.1743 0.0980 0.036 Uiso 1 1 calc R . .
H28B H 0.4073 0.1206 0.1439 0.036 Uiso 1 1 calc R . .
H28C H 0.4038 0.1478 0.0411 0.036 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
I1 0.02341(8) 0.02521(8) 0.02505(8) 0.00571(6) 0.00062(6) 0.00064(6)
I2 0.01809(7) 0.02214(8) 0.02554(7) 0.00062(6) 0.00083(6) 0.00170(5)
S1 0.0201(3) 0.0154(2) 0.0199(2) -0.0019(2) 0.0030(2) 0.00072(19)
S2 0.0180(3) 0.0146(2) 0.0193(2) -0.0021(2) 0.0017(2) 0.00167(19)
N1 0.0174(9) 0.0176(9) 0.0222(9) -0.0014(7) 0.0013(8) -0.0008(7)
N2 0.0169(9) 0.0187(9) 0.0186(8) -0.0002(7) 0.0045(7) -0.0022(7)
N3 0.0197(9) 0.0151(8) 0.0231(9) -0.0002(7) 0.0050(8) -0.0003(7)
N4 0.0136(9) 0.0189(9) 0.0160(8) -0.0006(7) 0.0031(7) -0.0007(7)
C1 0.0230(12) 0.0245(11) 0.0230(11) -0.0022(9) 0.0022(10) 0.0033(9)
C2 0.0263(13) 0.0207(11) 0.0389(13) -0.0014(10) 0.0038(11) -0.0067(9)
C3 0.0225(11) 0.0145(10) 0.0170(10) -0.0008(8) 0.0092(9) -0.0032(8)
C4 0.0244(12) 0.0147(10) 0.0241(11) 0.0024(9) 0.0082(9) -0.0003(8)
C5 0.0212(11) 0.0208(10) 0.0191(10) 0.0026(8) 0.0057(9) 0.0023(8)
C6 0.0187(11) 0.0195(10) 0.0166(10) 0.0006(8) 0.0053(8) 0.0008(8)
C7 0.0187(11) 0.0240(11) 0.0143(9) 0.0014(8) 0.0043(8) 0.0013(8)
C8 0.0171(11) 0.0224(11) 0.0164(10) 0.0012(8) 0.0042(8) 0.0010(8)
C9 0.0172(11) 0.0209(10) 0.0141(9) -0.0006(8) 0.0051(8) -0.0005(8)
C10 0.0177(11) 0.0224(11) 0.0196(10) -0.0007(9) 0.0022(9) 0.0033(8)
C11 0.0208(11) 0.0183(10) 0.0185(10) 0.0001(8) 0.0024(9) 0.0055(8)
C12 0.0197(11) 0.0172(10) 0.0178(10) 0.0017(8) 0.0042(9) 0.0028(8)
C13 0.0167(10) 0.0225(11) 0.0170(10) 0.0041(8) 0.0043(8) 0.0037(8)
C14 0.0171(11) 0.0210(10) 0.0222(10) -0.0015(9) 0.0026(9) -0.0031(8)
C15 0.0192(11) 0.0290(11) 0.0236(11) 0.0003(9) 0.0019(9) 0.0029(9)
C16 0.0270(12) 0.0217(11) 0.0261(11) -0.0030(9) 0.0046(10) -0.0091(9)
C17 0.0182(11) 0.0148(9) 0.0154(9) -0.0001(8) 0.0056(8) -0.0003(8)
C18 0.0250(12) 0.0120(10) 0.0177(10) 0.0019(8) 0.0056(9) 0.0008(8)
C19 0.0182(11) 0.0183(10) 0.0166(10) 0.0022(8) 0.0059(8) 0.0037(8)
C20 0.0164(10) 0.0180(10) 0.0140(9) 0.0005(8) 0.0034(8) 0.0007(8)
C21 0.0166(10) 0.0222(11) 0.0149(9) -0.0009(8) 0.0040(8) 0.0007(8)
C22 0.0169(11) 0.0210(10) 0.0166(10) -0.0027(8) 0.0010(8) 0.0003(8)
C23 0.0194(11) 0.0175(10) 0.0140(9) -0.0009(8) 0.0050(8) 0.0006(8)
C24 0.0178(11) 0.0206(11) 0.0224(10) 0.0016(9) 0.0014(9) 0.0037(8)
C25 0.0239(12) 0.0170(10) 0.0223(11) 0.0008(9) 0.0059(9) 0.0023(8)
C26 0.0226(11) 0.0136(10) 0.0174(10) 0.0002(8) 0.0051(9) 0.0017(8)
C27 0.0189(11) 0.0199(10) 0.0169(10) 0.0039(8) 0.0028(9) 0.0017(8)
C28 0.0227(12) 0.0212(11) 0.0259(11) -0.0007(9) 0.0016(10) -0.0062(9)

_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 C6 1.750(2) . ?
S1 C3 1.7551(18) . ?
S2 C17 1.7429(18) . ?
S2 C20 1.750(2) . ?
N1 C17 1.338(2) . ?
N1 C15 1.458(2) . ?
N1 C16 1.458(2) . ?
N2 C25 1.351(2) . ?
N2 C27 1.354(2) . ?
N2 C28 1.471(2) . ?
N3 C3 1.343(3) . ?
N3 C1 1.454(2) . ?
N3 C2 1.461(2) . ?
N4 C11 1.351(2) . ?
N4 C13 1.363(2) . ?
N4 C14 1.468(2) . ?
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 1.389(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(3) . ?
C7 C8 1.358(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(3) . ?
C8 H8 0.9500 . ?
C9 C12 1.406(3) . ?
C9 C10 1.416(3) . ?
C10 C11 1.364(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.366(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.399(3) . ?
C18 C19 1.396(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.410(3) . ?
C21 C22 1.360(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.432(3) . ?
C22 H22 0.9500 . ?
C23 C26 1.411(3) . ?
C23 C24 1.417(2) . ?
C24 C25 1.363(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.367(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C6 S1 C3 91.70(9) . . ?
C17 S2 C20 91.90(9) . . ?
C17 N1 C15 120.92(16) . . ?
C17 N1 C16 120.21(17) . . ?
C15 N1 C16 117.45(17) . . ?
C25 N2 C27 119.93(17) . . ?
C25 N2 C28 119.83(16) . . ?
C27 N2 C28 120.24(17) . . ?
C3 N3 C1 120.55(15) . . ?
C3 N3 C2 118.30(16) . . ?
C1 N3 C2 115.66(17) . . ?
C11 N4 C13 119.68(17) . . ?
C11 N4 C14 120.32(16) . . ?
C13 N4 C14 120.00(16) . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 C4 129.22(17) . . ?
N3 C3 S1 120.01(14) . . ?
C4 C3 S1 110.62(15) . . ?
C3 C4 C5 112.55(17) . . ?
C3 C4 H4 123.7 . . ?
C5 C4 H4 123.7 . . ?
C6 C5 C4 115.27(19) . . ?
C6 C5 H5 122.4 . . ?
C4 C5 H5 122.4 . . ?
C5 C6 C7 127.84(19) . . ?
C5 C6 S1 109.84(15) . . ?
C7 C6 S1 122.32(14) . . ?
C8 C7 C6 126.63(19) . . ?
C8 C7 H7 116.7 . . ?
C6 C7 H7 116.7 . . ?
C7 C8 C9 125.30(19) . . ?
C7 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C12 C9 C10 115.82(18) . . ?
C12 C9 C8 124.60(18) . . ?
C10 C9 C8 119.56(18) . . ?
C11 C10 C9 121.04(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N4 C11 C10 121.29(18) . . ?
N4 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C9 121.27(18) . . ?
C13 C12 H12 119.4 . . ?
C9 C12 H12 119.4 . . ?
N4 C13 C12 120.89(18) . . ?
N4 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 129.18(17) . . ?
N1 C17 S2 119.77(14) . . ?
C18 C17 S2 111.02(15) . . ?
C19 C18 C17 112.34(17) . . ?
C19 C18 H18 123.8 . . ?
C17 C18 H18 123.8 . . ?
C20 C19 C18 114.83(18) . . ?
C20 C19 H19 122.6 . . ?
C18 C19 H19 122.6 . . ?
C19 C20 C21 128.34(18) . . ?
C19 C20 S2 109.89(14) . . ?
C21 C20 S2 121.74(14) . . ?
C22 C21 C20 126.22(19) . . ?
C22 C21 H21 116.9 . . ?
C20 C21 H21 116.9 . . ?
C21 C22 C23 125.05(18) . . ?
C21 C22 H22 117.5 . . ?
C23 C22 H22 117.5 . . ?
C26 C23 C24 115.74(18) . . ?
C26 C23 C22 124.97(17) . . ?
C24 C23 C22 119.26(18) . . ?
C25 C24 C23 121.18(19) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
N2 C25 C24 121.02(18) . . ?
N2 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C23 120.84(17) . . ?
C27 C26 H26 119.6 . . ?
C23 C26 H26 119.6 . . ?
N2 C27 C26 121.29(18) . . ?
N2 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C1 N3 C3 C4 167.37(19) . . . . ?
C2 N3 C3 C4 14.6(3) . . . . ?
C1 N3 C3 S1 -17.6(2) . . . . ?
C2 N3 C3 S1 -170.29(14) . . . . ?
C6 S1 C3 N3 -174.49(16) . . . . ?
C6 S1 C3 C4 1.44(15) . . . . ?
N3 C3 C4 C5 173.84(19) . . . . ?
S1 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 -179.35(19) . . . . ?
C4 C5 C6 S1 0.2(2) . . . . ?
C3 S1 C6 C5 -0.90(15) . . . . ?
C3 S1 C6 C7 178.63(17) . . . . ?
C5 C6 C7 C8 178.05(19) . . . . ?
S1 C6 C7 C8 -1.4(3) . . . . ?
C6 C7 C8 C9 -176.99(19) . . . . ?
C7 C8 C9 C12 -0.9(3) . . . . ?
C7 C8 C9 C10 177.64(18) . . . . ?
C12 C9 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 C11 -179.51(18) . . . . ?
C13 N4 C11 C10 1.2(3) . . . . ?
C14 N4 C11 C10 -178.46(17) . . . . ?
C9 C10 C11 N4 -0.3(3) . . . . ?
C10 C9 C12 C13 1.2(3) . . . . ?
C8 C9 C12 C13 179.77(18) . . . . ?
C11 N4 C13 C12 -0.9(3) . . . . ?
C14 N4 C13 C12 178.80(17) . . . . ?
C9 C12 C13 N4 -0.4(3) . . . . ?
C15 N1 C17 C18 -175.50(19) . . . . ?
C16 N1 C17 C18 -9.4(3) . . . . ?
C15 N1 C17 S2 6.5(2) . . . . ?
C16 N1 C17 S2 172.58(14) . . . . ?
C20 S2 C17 N1 177.21(16) . . . . ?
C20 S2 C17 C18 -1.12(15) . . . . ?
N1 C17 C18 C19 -177.21(19) . . . . ?
S2 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C21 177.48(18) . . . . ?
C18 C19 C20 S2 -0.7(2) . . . . ?
C17 S2 C20 C19 1.03(14) . . . . ?
C17 S2 C20 C21 -177.30(16) . . . . ?
C19 C20 C21 C22 -174.90(19) . . . . ?
S2 C20 C21 C22 3.1(3) . . . . ?
C20 C21 C22 C23 177.15(18) . . . . ?
C21 C22 C23 C26 2.1(3) . . . . ?
C21 C22 C23 C24 -176.03(18) . . . . ?
C26 C23 C24 C25 -0.1(3) . . . . ?
C22 C23 C24 C25 178.24(18) . . . . ?
C27 N2 C25 C24 -1.4(3) . . . . ?
C28 N2 C25 C24 177.91(18) . . . . ?
C23 C24 C25 N2 1.0(3) . . . . ?
C24 C23 C26 C27 -0.6(3) . . . . ?
C22 C23 C26 C27 -178.76(18) . . . . ?
C25 N2 C27 C26 0.7(3) . . . . ?
C28 N2 C27 C26 -178.55(18) . . . . ?
C23 C26 C27 N2 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.088

# Attachment '- 3c.cif'

data_shelx(3c)
_database_code_depnum_ccdc_archive 'CCDC 843804'
#TrackingRef '- 3c.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2 O5 S2'
_chemical_formula_weight         436.53

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   9.621(7)
_cell_length_b                   15.234(11)
_cell_length_c                   13.948(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.849(14)
_cell_angle_gamma                90.00
_cell_volume                     2040(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7302
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      28.0

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_T_max  0.9597
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
Rigaku CrystalClear-SM Expert 2.0 r2
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17523
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0925
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.03
_reflns_number_total             7038
_reflns_number_gt                6324
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.7.0'

_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^)+(0.0489P)^2^+0.3737P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_number_reflns         7038
_refine_ls_number_parameters     571
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.101
_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
S1 S 1.00877(12) 0.75883(8) 0.37291(8) 0.0199(3) Uani 1 1 d . . .
S2 S 0.00511(12) 0.22357(9) 0.13019(9) 0.0247(3) Uani 1 1 d . . .
S3 S 0.61953(11) 0.19253(9) 0.50211(8) 0.0195(3) Uani 1 1 d . . .
O1 O 0.5568(4) 0.5432(2) 0.6791(2) 0.0260(8) Uani 1 1 d . . .
H1 H 0.5668 0.5825 0.6400 0.039 Uiso 1 1 calc R . .
O2 O 0.6405(4) 0.1303(2) 0.5810(2) 0.0292(8) Uani 1 1 d . . .
O3 O 0.4850(3) 0.1785(2) 0.4467(2) 0.0284(8) Uani 1 1 d . . .
O4 O 0.7355(3) 0.1960(2) 0.4416(2) 0.0283(8) Uani 1 1 d . . .
O5 O 0.6167(4) 0.4427(3) 0.2791(2) 0.0329(9) Uani 1 1 d . . .
H5 H 0.5566 0.4804 0.2693 0.049 Uiso 1 1 calc R . .
N1 N 1.1192(4) 0.2786(3) 0.3883(3) 0.0196(9) Uani 1 1 d . . .
N2 N 0.9261(4) 0.9273(3) 0.3651(3) 0.0264(10) Uani 1 1 d . . .
N3 N -0.1248(8) -0.2556(3) 0.1138(3) 0.0559(18) Uani 1 1 d . . .
N4 N 0.0908(4) 0.3917(3) 0.1415(3) 0.0341(12) Uani 1 1 d . . .
C1 C 1.1495(5) 0.1837(4) 0.3882(3) 0.0263(11) Uani 1 1 d . . .
H1A H 1.1468 0.1628 0.3232 0.039 Uiso 1 1 calc R . .
H1B H 1.0810 0.1532 0.4225 0.039 Uiso 1 1 calc R . .
H1C H 1.2403 0.1735 0.4189 0.039 Uiso 1 1 calc R . .
C2 C 1.2234(5) 0.3366(4) 0.3956(3) 0.0226(11) Uani 1 1 d . . .
H2 H 1.3149 0.3167 0.4027 0.027 Uiso 1 1 calc R . .
C3 C 1.1975(5) 0.4247(4) 0.3927(3) 0.0252(12) Uani 1 1 d . . .
H3 H 1.2719 0.4638 0.3967 0.030 Uiso 1 1 calc R . .
C4 C 1.0600(5) 0.4577(3) 0.3839(3) 0.0194(11) Uani 1 1 d . . .
C5 C 0.9540(5) 0.3929(4) 0.3779(3) 0.0225(11) Uani 1 1 d . . .
H5A H 0.8612 0.4104 0.3720 0.027 Uiso 1 1 calc R . .
C6 C 0.9846(5) 0.3058(3) 0.3805(3) 0.0223(11) Uani 1 1 d . . .
H6 H 0.9131 0.2647 0.3770 0.027 Uiso 1 1 calc R . .
C7 C 1.0350(5) 0.5500(3) 0.3815(3) 0.0198(11) Uani 1 1 d . . .
H7 H 1.1119 0.5871 0.3869 0.024 Uiso 1 1 calc R . .
C8 C 0.9067(5) 0.5877(3) 0.3717(3) 0.0207(11) Uani 1 1 d . . .
H8 H 0.8306 0.5499 0.3672 0.025 Uiso 1 1 calc R . .
C9 C 0.8773(5) 0.6792(4) 0.3679(3) 0.0222(11) Uani 1 1 d . . .
C10 C 0.7471(5) 0.7202(4) 0.3620(3) 0.0240(11) Uani 1 1 d . . .
H10 H 0.6640 0.6888 0.3599 0.029 Uiso 1 1 calc R . .
C11 C 0.7509(5) 0.8105(4) 0.3596(3) 0.0259(12) Uani 1 1 d . . .
H11 H 0.6716 0.8455 0.3546 0.031 Uiso 1 1 calc R . .
C12 C 0.8858(5) 0.8441(4) 0.3653(3) 0.0216(11) Uani 1 1 d . . .
C13 C 0.8217(5) 0.9970(4) 0.3577(4) 0.0320(13) Uani 1 1 d . . .
H13A H 0.7655 0.9907 0.2986 0.048 Uiso 1 1 calc R . .
H13B H 0.8674 1.0530 0.3588 0.048 Uiso 1 1 calc R . .
H13C H 0.7636 0.9930 0.4109 0.048 Uiso 1 1 calc R . .
C14 C 1.0724(5) 0.9531(3) 0.3750(4) 0.0286(13) Uani 1 1 d . . .
H14A H 1.1299 0.9015 0.3777 0.043 Uiso 1 1 calc R . .
H14B H 1.0896 0.9864 0.4330 0.043 Uiso 1 1 calc R . .
H14C H 1.0939 0.9882 0.3209 0.043 Uiso 1 1 calc R . .
C15 C -0.1573(10) -0.3502(5) 0.1125(5) 0.083(3) Uani 1 1 d . . .
H15A H -0.0852 -0.3816 0.0826 0.125 Uiso 1 1 calc R . .
H15B H -0.2448 -0.3598 0.0769 0.125 Uiso 1 1 calc R . .
H15C H -0.1629 -0.3708 0.1772 0.125 Uiso 1 1 calc R . .
C16 C 0.0114(9) -0.2305(5) 0.1179(4) 0.059(2) Uani 1 1 d . . .
H16 H 0.0806 -0.2732 0.1200 0.071 Uiso 1 1 calc R . .
C17 C 0.0489(7) -0.1433(4) 0.1188(4) 0.0424(16) Uani 1 1 d . . .
H17 H 0.1424 -0.1275 0.1208 0.051 Uiso 1 1 calc R . .
C18 C -0.0561(6) -0.0774(4) 0.1167(3) 0.0327(14) Uani 1 1 d . . .
C19 C -0.1940(7) -0.1081(4) 0.1117(4) 0.0413(16) Uani 1 1 d . . .
H19 H -0.2664 -0.0675 0.1093 0.050 Uiso 1 1 calc R . .
C20 C -0.2252(8) -0.1947(4) 0.1101(4) 0.0486(18) Uani 1 1 d . . .
H20 H -0.3180 -0.2122 0.1065 0.058 Uiso 1 1 calc R . .
C21 C -0.0265(6) 0.0147(4) 0.1182(3) 0.0304(13) Uani 1 1 d . . .
H21 H -0.1021 0.0528 0.1123 0.036 Uiso 1 1 calc R . .
C22 C 0.1020(6) 0.0510(4) 0.1276(4) 0.0311(14) Uani 1 1 d . . .
H22 H 0.1770 0.0123 0.1311 0.037 Uiso 1 1 calc R . .
C23 C 0.1349(5) 0.1430(4) 0.1326(3) 0.0291(13) Uani 1 1 d . . .
C24 C 0.2630(5) 0.1815(4) 0.1398(3) 0.0318(13) Uani 1 1 d . . .
H24 H 0.3449 0.1489 0.1418 0.038 Uiso 1 1 calc R . .
C25 C 0.2635(5) 0.2723(4) 0.1441(3) 0.0330(14) Uani 1 1 d . . .
H25 H 0.3442 0.3060 0.1496 0.040 Uiso 1 1 calc R . .
C26 C 0.1300(5) 0.3075(4) 0.1392(4) 0.0252(12) Uani 1 1 d . . .
C27 C -0.0549(5) 0.4188(4) 0.1303(4) 0.0333(14) Uani 1 1 d . . .
H27A H -0.0752 0.4411 0.0665 0.050 Uiso 1 1 calc R . .
H27B H -0.0715 0.4639 0.1763 0.050 Uiso 1 1 calc R . .
H27C H -0.1137 0.3693 0.1408 0.050 Uiso 1 1 calc R . .
C28 C 0.1984(6) 0.4605(4) 0.1421(4) 0.0397(15) Uani 1 1 d . . .
H28A H 0.2664 0.4504 0.1945 0.059 Uiso 1 1 calc R . .
H28B H 0.1559 0.5169 0.1496 0.059 Uiso 1 1 calc R . .
H28C H 0.2430 0.4590 0.0826 0.059 Uiso 1 1 calc R . .
C29 C 0.5728(5) 0.4636(3) 0.6360(3) 0.0163(10) Uani 1 1 d . . .
C30 C 0.5998(4) 0.3905(3) 0.6949(3) 0.0180(10) Uani 1 1 d . . .
H30 H 0.6068 0.3969 0.7613 0.022 Uiso 1 1 calc R . .
C31 C 0.6161(5) 0.3086(3) 0.6543(3) 0.0199(10) Uani 1 1 d . . .
H31 H 0.6347 0.2602 0.6937 0.024 Uiso 1 1 calc R . .
C32 C 0.6051(5) 0.2979(3) 0.5554(3) 0.0195(10) Uani 1 1 d . . .
C33 C 0.5803(5) 0.3693(3) 0.4971(3) 0.0210(11) Uani 1 1 d . . .
H33 H 0.5739 0.3618 0.4308 0.025 Uiso 1 1 calc R . .
C34 C 0.5643(5) 0.4537(3) 0.5356(3) 0.0186(10) Uani 1 1 d . . .
H34 H 0.5484 0.5019 0.4955 0.022 Uiso 1 1 calc R . .
C35 C 0.6128(5) 0.3864(4) 0.2042(3) 0.0217(11) Uani 1 1 d . . .
C36 C 0.5848(5) 0.4114(4) 0.1082(3) 0.0226(11) Uani 1 1 d . . .
H36 H 0.5653 0.4698 0.0933 0.027 Uiso 1 1 calc R . .
C37 C 0.5859(5) 0.3511(4) 0.0367(3) 0.0269(13) Uani 1 1 d . . .
H37 H 0.5666 0.3688 -0.0267 0.032 Uiso 1 1 calc R . .
C38 C 0.6159(4) 0.2614(4) 0.0569(3) 0.0210(11) Uani 1 1 d . A .
C39 C 0.6444(5) 0.2372(4) 0.1518(3) 0.0255(12) Uani 1 1 d . . .
H39 H 0.6664 0.1790 0.1663 0.031 Uiso 1 1 calc R . .
C40 C 0.6408(5) 0.2976(4) 0.2254(3) 0.0249(12) Uani 1 1 d . . .
H40 H 0.6569 0.2797 0.2889 0.030 Uiso 1 1 calc R . .
S4 S 0.61852(12) 0.18324(10) -0.03504(8) 0.0290(3) Uani 1 1 d D . .
O6 O 0.7556(6) 0.1398(4) -0.0236(4) 0.0390(18) Uani 0.671(7) 1 d PD A 1
O7 O 0.5929(6) 0.2275(4) -0.1258(3) 0.0405(19) Uani 0.671(7) 1 d PD A 1
O8 O 0.5061(6) 0.1208(5) -0.0156(4) 0.049(2) Uani 0.671(7) 1 d PD A 1
O6' O 0.7163(11) 0.2191(8) -0.1065(7) 0.041(4) Uani 0.329(7) 1 d PD A 2
O7' O 0.4756(8) 0.1821(8) -0.0865(7) 0.031(3) Uani 0.329(7) 1 d PD A 2
O8' O 0.6528(15) 0.0981(7) 0.0087(8) 0.052(5) Uani 0.329(7) 1 d PD A 2
O10 O 0.4860(5) 0.5895(3) 0.2548(3) 0.0416(10) Uani 1 1 d D . .
H10A H 0.456(6) 0.621(3) 0.304(2) 0.062 Uiso 1 1 d D . .
H10B H 0.466(6) 0.628(3) 0.207(2) 0.062 Uiso 1 1 d D . .
O9 O 0.4877(7) 0.5029(4) 0.8726(4) 0.0854(19) Uani 1 1 d D . .
H9B H 0.484(9) 0.535(4) 0.818(3) 0.128 Uiso 1 1 d D . .
H9A H 0.457(9) 0.544(4) 0.913(4) 0.128 Uiso 1 1 d 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
S1 0.0179(6) 0.0177(7) 0.0241(6) -0.0018(5) 0.0016(5) 0.0009(5)
S2 0.0211(6) 0.0265(7) 0.0268(6) 0.0024(6) 0.0032(5) -0.0003(5)
S3 0.0168(5) 0.0138(6) 0.0283(6) -0.0002(6) 0.0039(4) 0.0003(5)
O1 0.042(2) 0.0118(19) 0.0247(18) 0.0000(15) 0.0029(16) 0.0030(16)
O2 0.039(2) 0.020(2) 0.0294(19) 0.0064(16) 0.0052(16) 0.0053(17)
O3 0.0219(16) 0.020(2) 0.042(2) -0.0061(18) -0.0050(14) 0.0013(16)
O4 0.0242(16) 0.019(2) 0.044(2) -0.0056(18) 0.0154(14) 0.0003(16)
O5 0.037(2) 0.039(3) 0.0221(18) -0.0082(17) -0.0025(16) 0.0104(18)
N1 0.024(2) 0.014(2) 0.020(2) -0.0023(17) 0.0004(17) 0.0025(17)
N2 0.019(2) 0.019(3) 0.041(3) -0.003(2) -0.0004(19) 0.0052(19)
N3 0.124(6) 0.017(3) 0.025(3) -0.003(2) -0.007(3) 0.001(3)
N4 0.019(2) 0.037(3) 0.047(3) 0.003(2) 0.009(2) -0.004(2)
C1 0.032(3) 0.018(3) 0.027(2) 0.003(2) -0.007(2) -0.002(3)
C2 0.016(2) 0.027(3) 0.024(3) 0.000(2) 0.001(2) 0.000(2)
C3 0.022(3) 0.026(3) 0.026(3) 0.003(2) -0.001(2) -0.007(2)
C4 0.023(3) 0.022(3) 0.013(2) 0.003(2) -0.0020(19) 0.001(2)
C5 0.016(2) 0.030(3) 0.021(3) -0.002(2) 0.0004(19) 0.000(2)
C6 0.023(3) 0.018(3) 0.026(3) 0.000(2) 0.002(2) -0.003(2)
C7 0.022(2) 0.017(3) 0.020(2) -0.001(2) -0.0002(19) -0.006(2)
C8 0.028(3) 0.014(3) 0.020(2) 0.003(2) 0.004(2) -0.004(2)
C9 0.024(2) 0.019(3) 0.024(2) 0.005(2) 0.0006(19) -0.001(2)
C10 0.019(2) 0.027(3) 0.026(3) 0.004(2) 0.004(2) -0.003(2)
C11 0.020(3) 0.027(3) 0.030(3) -0.001(2) -0.002(2) 0.002(2)
C12 0.023(3) 0.025(3) 0.017(2) -0.005(2) 0.001(2) 0.000(2)
C13 0.028(3) 0.019(3) 0.049(3) -0.001(3) 0.000(2) 0.010(2)
C14 0.026(3) 0.015(3) 0.046(3) -0.007(3) 0.007(2) -0.001(2)
C15 0.187(10) 0.020(4) 0.041(4) 0.001(3) -0.001(5) -0.009(5)
C16 0.120(7) 0.038(5) 0.019(3) 0.000(3) -0.001(4) 0.031(5)
C17 0.076(5) 0.032(4) 0.019(3) 0.001(3) 0.007(3) 0.014(3)
C18 0.055(4) 0.032(4) 0.011(2) 0.001(2) 0.002(2) 0.004(3)
C19 0.065(4) 0.038(4) 0.021(3) 0.000(3) 0.004(3) -0.005(3)
C20 0.095(5) 0.027(4) 0.023(3) 0.001(3) -0.006(3) -0.013(4)
C21 0.041(3) 0.028(3) 0.022(3) 0.005(2) 0.005(2) 0.013(3)
C22 0.036(3) 0.035(4) 0.022(3) -0.002(2) 0.005(2) 0.007(3)
C23 0.035(3) 0.032(4) 0.020(3) 0.003(2) 0.005(2) 0.010(3)
C24 0.018(2) 0.049(4) 0.029(3) 0.000(3) 0.006(2) 0.010(3)
C25 0.024(3) 0.047(4) 0.028(3) 0.004(3) 0.005(2) -0.003(3)
C26 0.020(3) 0.028(3) 0.027(3) -0.003(2) 0.002(2) -0.003(2)
C27 0.034(3) 0.029(4) 0.038(3) 0.007(3) 0.008(3) 0.002(3)
C28 0.043(3) 0.032(4) 0.045(3) 0.001(3) 0.006(3) -0.015(3)
C29 0.017(2) 0.009(2) 0.023(2) -0.001(2) 0.0028(19) -0.0012(19)
C30 0.021(2) 0.020(3) 0.014(2) -0.002(2) -0.0011(18) 0.003(2)
C31 0.020(2) 0.014(3) 0.025(2) 0.005(2) 0.002(2) 0.002(2)
C32 0.014(2) 0.013(3) 0.032(3) -0.002(2) 0.002(2) 0.0019(19)
C33 0.025(3) 0.016(3) 0.022(2) -0.003(2) 0.002(2) -0.001(2)
C34 0.019(2) 0.011(3) 0.026(2) 0.009(2) 0.0014(19) -0.003(2)
C35 0.019(2) 0.024(3) 0.021(2) -0.007(2) 0.001(2) -0.005(2)
C36 0.023(2) 0.028(3) 0.017(2) -0.004(2) 0.002(2) -0.001(2)
C37 0.026(3) 0.039(4) 0.016(2) 0.000(2) 0.001(2) -0.009(2)
C38 0.013(2) 0.034(3) 0.017(2) -0.003(2) 0.0058(18) -0.006(2)
C39 0.019(2) 0.027(3) 0.031(3) 0.003(2) 0.002(2) 0.007(2)
C40 0.024(3) 0.033(3) 0.018(2) -0.002(2) 0.002(2) -0.006(2)
S4 0.0303(6) 0.0329(8) 0.0240(6) -0.0080(6) 0.0046(5) 0.0030(7)
O6 0.039(4) 0.033(4) 0.043(4) -0.014(3) -0.006(3) 0.015(3)
O7 0.058(5) 0.039(4) 0.024(3) -0.003(3) 0.000(3) 0.004(3)
O8 0.054(4) 0.058(5) 0.035(4) -0.013(3) 0.008(3) -0.022(4)
O6' 0.042(8) 0.062(10) 0.023(6) -0.020(6) 0.021(5) -0.009(6)
O7' 0.020(5) 0.031(7) 0.041(7) -0.024(6) -0.014(4) 0.016(5)
O8' 0.075(11) 0.054(11) 0.027(7) -0.010(6) 0.002(7) 0.039(9)
O10 0.071(3) 0.025(2) 0.029(2) 0.0017(17) 0.003(2) 0.009(2)
O9 0.155(6) 0.043(4) 0.062(3) 0.002(3) 0.039(4) 0.000(4)

_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 C9 1.750(5) . ?
S1 C12 1.755(5) . ?
S2 C23 1.749(5) . ?
S2 C26 1.753(6) . ?
S3 O4 1.444(3) . ?
S3 O2 1.457(4) . ?
S3 O3 1.478(3) . ?
S3 C32 1.778(5) . ?
O1 C29 1.367(6) . ?
O1 H1 0.8200 . ?
O5 C35 1.351(6) . ?
O5 H5 0.8200 . ?
N1 C2 1.335(6) . ?
N1 C6 1.357(6) . ?
N1 C1 1.473(7) . ?
N2 C12 1.326(7) . ?
N2 C14 1.458(6) . ?
N2 C13 1.460(6) . ?
N3 C20 1.338(9) . ?
N3 C16 1.363(9) . ?
N3 C15 1.474(8) . ?
N4 C26 1.337(7) . ?
N4 C27 1.460(6) . ?
N4 C28 1.472(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.418(7) . ?
C4 C7 1.428(7) . ?
C5 C6 1.358(7) . ?
C5 H5A 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.359(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.424(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(7) . ?
C10 C11 1.376(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.376(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.423(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.404(8) . ?
C18 C21 1.431(8) . ?
C19 C20 1.353(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.352(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.438(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.363(7) . ?
C24 C25 1.385(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(7) . ?
C25 H25 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.398(6) . ?
C29 C34 1.404(6) . ?
C30 C31 1.383(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.368(7) . ?
C33 C34 1.406(7) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.401(6) . ?
C35 C40 1.406(7) . ?
C36 C37 1.356(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.421(7) . ?
C37 H37 0.9300 . ?
C38 C39 1.384(6) . ?
C38 S4 1.751(5) . ?
C39 C40 1.381(7) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
S4 O7 1.442(5) . ?
S4 O8' 1.462(8) . ?
S4 O6 1.475(5) . ?
S4 O8 1.479(6) . ?
S4 O7' 1.508(7) . ?
S4 O6' 1.517(7) . ?
O10 H10A 0.898(10) . ?
O10 H10B 0.899(10) . ?
O9 H9B 0.903(10) . ?
O9 H9A 0.902(10) . ?

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
C9 S1 C12 91.6(2) . . ?
C23 S2 C26 91.5(3) . . ?
O4 S3 O2 113.1(2) . . ?
O4 S3 O3 112.5(2) . . ?
O2 S3 O3 111.9(2) . . ?
O4 S3 C32 107.2(2) . . ?
O2 S3 C32 106.4(2) . . ?
O3 S3 C32 105.0(2) . . ?
C29 O1 H1 109.5 . . ?
C35 O5 H5 109.5 . . ?
C2 N1 C6 120.7(4) . . ?
C2 N1 C1 120.1(4) . . ?
C6 N1 C1 119.2(4) . . ?
C12 N2 C14 122.5(4) . . ?
C12 N2 C13 119.7(4) . . ?
C14 N2 C13 117.8(4) . . ?
C20 N3 C16 119.7(6) . . ?
C20 N3 C15 121.7(7) . . ?
C16 N3 C15 118.5(7) . . ?
C26 N4 C27 122.6(5) . . ?
C26 N4 C28 118.9(5) . . ?
C27 N4 C28 117.9(5) . . ?
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 C3 120.9(5) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 115.0(5) . . ?
C3 C4 C7 120.5(5) . . ?
C5 C4 C7 124.4(5) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
N1 C6 C5 120.3(5) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C4 124.6(5) . . ?
C8 C7 H7 117.7 . . ?
C4 C7 H7 117.7 . . ?
C7 C8 C9 126.4(5) . . ?
C7 C8 H8 116.8 . . ?
C9 C8 H8 116.8 . . ?
C10 C9 C8 127.9(5) . . ?
C10 C9 S1 109.6(4) . . ?
C8 C9 S1 122.4(4) . . ?
C11 C10 C9 115.0(5) . . ?
C11 C10 H10 122.5 . . ?
C9 C10 H10 122.5 . . ?
C10 C11 C12 113.1(5) . . ?
C10 C11 H11 123.4 . . ?
C12 C11 H11 123.4 . . ?
N2 C12 C11 128.6(5) . . ?
N2 C12 S1 120.7(4) . . ?
C11 C12 S1 110.7(4) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 121.5(7) . . ?
N3 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 119.7(7) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 115.7(6) . . ?
C19 C18 C21 120.9(6) . . ?
C17 C18 C21 123.4(6) . . ?
C20 C19 C18 122.2(7) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
N3 C20 C19 121.2(7) . . ?
N3 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C18 125.6(5) . . ?
C22 C21 H21 117.2 . . ?
C18 C21 H21 117.2 . . ?
C21 C22 C23 126.9(5) . . ?
C21 C22 H22 116.6 . . ?
C23 C22 H22 116.6 . . ?
C24 C23 C22 128.2(5) . . ?
C24 C23 S2 109.9(5) . . ?
C22 C23 S2 121.9(4) . . ?
C23 C24 C25 115.7(5) . . ?
C23 C24 H24 122.2 . . ?
C25 C24 H24 122.2 . . ?
C24 C25 C26 112.5(5) . . ?
C24 C25 H25 123.7 . . ?
C26 C25 H25 123.7 . . ?
N4 C26 C25 129.0(5) . . ?
N4 C26 S2 120.5(4) . . ?
C25 C26 S2 110.4(5) . . ?
N4 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 C29 C30 118.0(4) . . ?
O1 C29 C34 122.2(4) . . ?
C30 C29 C34 119.8(4) . . ?
C31 C30 C29 120.0(4) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.6(4) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 119.8(5) . . ?
C33 C32 S3 119.0(4) . . ?
C31 C32 S3 121.2(4) . . ?
C32 C33 C34 121.3(4) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C29 C34 C33 118.5(4) . . ?
C29 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
O5 C35 C36 124.1(5) . . ?
O5 C35 C40 116.9(4) . . ?
C36 C35 C40 119.0(5) . . ?
C37 C36 C35 120.5(5) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 121.1(5) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C39 C38 C37 118.1(5) . . ?
C39 C38 S4 120.5(4) . . ?
C37 C38 S4 121.4(4) . . ?
C40 C39 C38 121.4(5) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C35 119.8(4) . . ?
C39 C40 H40 120.1 . . ?
C35 C40 H40 120.1 . . ?
O7 S4 O8' 143.4(5) . . ?
O7 S4 O6 113.8(3) . . ?
O8' S4 O6 51.8(6) . . ?
O7 S4 O8 112.2(4) . . ?
O8' S4 O8 60.0(6) . . ?
O6 S4 O8 110.6(4) . . ?
O7 S4 O7' 59.4(5) . . ?
O8' S4 O7' 111.2(8) . . ?
O6 S4 O7' 145.8(5) . . ?
O8 S4 O7' 54.9(5) . . ?
O7 S4 O6' 48.1(5) . . ?
O8' S4 O6' 117.4(7) . . ?
O6 S4 O6' 69.1(6) . . ?
O8 S4 O6' 147.7(5) . . ?
O7' S4 O6' 106.1(7) . . ?
O7 S4 C38 108.4(3) . . ?
O8' S4 C38 108.2(5) . . ?
O6 S4 C38 106.4(3) . . ?
O8 S4 C38 104.9(3) . . ?
O7' S4 C38 107.4(4) . . ?
O6' S4 C38 106.0(5) . . ?
H10A O10 H10B 99.5(15) . . ?
H9B O9 H9A 99.7(15) . . ?

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 N1 C2 C3 -1.9(7) . . . . ?
C1 N1 C2 C3 178.0(4) . . . . ?
N1 C2 C3 C4 1.3(7) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C2 C3 C4 C7 179.7(4) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C7 C4 C5 C6 179.9(4) . . . . ?
C2 N1 C6 C5 1.5(7) . . . . ?
C1 N1 C6 C5 -178.3(4) . . . . ?
C4 C5 C6 N1 -0.6(7) . . . . ?
C3 C4 C7 C8 179.0(4) . . . . ?
C5 C4 C7 C8 -1.0(7) . . . . ?
C4 C7 C8 C9 -179.2(4) . . . . ?
C7 C8 C9 C10 -177.1(4) . . . . ?
C7 C8 C9 S1 1.4(7) . . . . ?
C12 S1 C9 C10 -0.8(3) . . . . ?
C12 S1 C9 C8 -179.5(4) . . . . ?
C8 C9 C10 C11 179.9(5) . . . . ?
S1 C9 C10 C11 1.2(5) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C14 N2 C12 C11 177.8(5) . . . . ?
C13 N2 C12 C11 -0.3(8) . . . . ?
C14 N2 C12 S1 -2.6(7) . . . . ?
C13 N2 C12 S1 179.4(4) . . . . ?
C10 C11 C12 N2 -179.8(5) . . . . ?
C10 C11 C12 S1 0.5(5) . . . . ?
C9 S1 C12 N2 -179.5(4) . . . . ?
C9 S1 C12 C11 0.2(4) . . . . ?
C20 N3 C16 C17 0.4(9) . . . . ?
C15 N3 C16 C17 179.7(5) . . . . ?
N3 C16 C17 C18 0.8(8) . . . . ?
C16 C17 C18 C19 -1.3(7) . . . . ?
C16 C17 C18 C21 179.5(5) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C21 C18 C19 C20 180.0(5) . . . . ?
C16 N3 C20 C19 -0.9(8) . . . . ?
C15 N3 C20 C19 179.8(5) . . . . ?
C18 C19 C20 N3 0.3(9) . . . . ?
C19 C18 C21 C22 176.6(5) . . . . ?
C17 C18 C21 C22 -4.2(8) . . . . ?
C18 C21 C22 C23 -177.7(5) . . . . ?
C21 C22 C23 C24 -178.4(5) . . . . ?
C21 C22 C23 S2 1.7(8) . . . . ?
C26 S2 C23 C24 0.0(4) . . . . ?
C26 S2 C23 C22 179.9(4) . . . . ?
C22 C23 C24 C25 -179.6(5) . . . . ?
S2 C23 C24 C25 0.3(6) . . . . ?
C23 C24 C25 C26 -0.5(7) . . . . ?
C27 N4 C26 C25 176.6(5) . . . . ?
C28 N4 C26 C25 5.1(9) . . . . ?
C27 N4 C26 S2 -4.2(7) . . . . ?
C28 N4 C26 S2 -175.7(4) . . . . ?
C24 C25 C26 N4 179.8(5) . . . . ?
C24 C25 C26 S2 0.5(6) . . . . ?
C23 S2 C26 N4 -179.6(5) . . . . ?
C23 S2 C26 C25 -0.2(4) . . . . ?
O1 C29 C30 C31 179.7(4) . . . . ?
C34 C29 C30 C31 -0.9(7) . . . . ?
C29 C30 C31 C32 -0.4(7) . . . . ?
C30 C31 C32 C33 1.2(7) . . . . ?
C30 C31 C32 S3 -177.7(3) . . . . ?
O4 S3 C32 C33 60.7(4) . . . . ?
O2 S3 C32 C33 -178.0(4) . . . . ?
O3 S3 C32 C33 -59.2(4) . . . . ?
O4 S3 C32 C31 -120.4(4) . . . . ?
O2 S3 C32 C31 0.9(4) . . . . ?
O3 S3 C32 C31 119.7(4) . . . . ?
C31 C32 C33 C34 -0.6(7) . . . . ?
S3 C32 C33 C34 178.3(4) . . . . ?
O1 C29 C34 C33 -179.2(4) . . . . ?
C30 C29 C34 C33 1.4(6) . . . . ?
C32 C33 C34 C29 -0.7(7) . . . . ?
O5 C35 C36 C37 178.5(4) . . . . ?
C40 C35 C36 C37 -0.6(7) . . . . ?
C35 C36 C37 C38 -0.3(7) . . . . ?
C36 C37 C38 C39 -0.1(7) . . . . ?
C36 C37 C38 S4 -179.6(4) . . . . ?
C37 C38 C39 C40 1.5(6) . . . . ?
S4 C38 C39 C40 -179.0(4) . . . . ?
C38 C39 C40 C35 -2.4(7) . . . . ?
O5 C35 C40 C39 -177.3(4) . . . . ?
C36 C35 C40 C39 1.9(7) . . . . ?
C39 C38 S4 O7 -176.9(4) . . . . ?
C37 C38 S4 O7 2.6(5) . . . . ?
C39 C38 S4 O8' 0.3(7) . . . . ?
C37 C38 S4 O8' 179.8(7) . . . . ?
C39 C38 S4 O6 -54.1(5) . . . . ?
C37 C38 S4 O6 125.4(4) . . . . ?
C39 C38 S4 O8 63.1(5) . . . . ?
C37 C38 S4 O8 -117.4(5) . . . . ?
C39 C38 S4 O7' 120.4(6) . . . . ?
C37 C38 S4 O7' -60.1(7) . . . . ?
C39 C38 S4 O6' -126.5(6) . . . . ?
C37 C38 S4 O6' 53.0(7) . . . . ?

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
O1 H1 O3 0.82 1.94 2.719(5) 158.1 2_656
O5 H5 O10 0.82 1.80 2.577(5) 157.1 .
O10 H10A O2 0.898(10) 1.91(3) 2.736(5) 152(5) 2_656
O10 H10B O7 0.899(10) 1.955(18) 2.837(7) 167(5) 2_655
O10 H10B O7' 0.899(10) 1.99(3) 2.785(10) 147(5) 2_655
O10 H10B O6' 0.899(10) 2.58(3) 3.380(12) 149(5) 2_655
O10 H10B S4 0.899(10) 2.62(2) 3.469(4) 158(5) 2_655
O9 H9B O1 0.903(10) 2.10(4) 2.889(6) 145(6) .
O9 H9A O8' 0.902(10) 1.77(3) 2.640(14) 160(9) 2_656
O9 H9A O8 0.902(10) 1.86(5) 2.682(9) 150(8) 2_656
O9 H9A S4 0.902(10) 2.847(15) 3.747(6) 175(7) 2_656

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072

# Attachment '- 3i.cif'

data_shelx(3i)
_database_code_depnum_ccdc_archive 'CCDC 843805'
#TrackingRef '- 3i.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N3 O4 S2'
_chemical_formula_weight         463.60

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.965(3)
_cell_length_b                   16.675(5)
_cell_length_c                   17.439(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.690(5)
_cell_angle_gamma                90.00
_cell_volume                     2276.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7253
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19233
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4013
_reflns_number_gt                3571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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^)+(0.0738P)^2^+0.9827P] 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         4013
_refine_ls_number_parameters     398
_refine_ls_number_restraints     308
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.003
_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 0.70889(9) 0.32954(4) 0.07831(4) 0.0270(2) Uani 1 1 d . . .
N1 N 0.9908(3) 0.36287(15) 0.01902(14) 0.0370(6) Uani 1 1 d . . .
N2 N -0.0927(3) 0.17532(14) 0.18800(14) 0.0342(6) Uani 1 1 d . . .
C1 C 1.0986(4) 0.35455(17) -0.03897(16) 0.0338(7) Uani 1 1 d . . .
H1A H 1.1116 0.2976 -0.0504 0.051 Uiso 1 1 calc R . .
H1B H 1.2110 0.3779 -0.0189 0.051 Uiso 1 1 calc R . .
H1C H 1.0459 0.3825 -0.0868 0.051 Uiso 1 1 calc R . .
C2 C 1.0378(4) 0.41948(17) 0.08213(18) 0.0404(7) Uani 1 1 d . . .
H2A H 0.9653 0.4672 0.0721 0.061 Uiso 1 1 calc R . .
H2B H 1.1577 0.4349 0.0858 0.061 Uiso 1 1 calc R . .
H2C H 1.0222 0.3947 0.1313 0.061 Uiso 1 1 calc R . .
C3 C 0.8420(3) 0.32098(15) 0.01009(15) 0.0268(6) Uani 1 1 d . . .
C4 C 0.7771(3) 0.26776(15) -0.04864(15) 0.0262(6) Uani 1 1 d . . .
H4 H 0.8306 0.2558 -0.0916 0.031 Uiso 1 1 calc R . .
C5 C 0.6224(3) 0.23331(15) -0.03732(14) 0.0266(6) Uani 1 1 d . . .
H5 H 0.5612 0.1954 -0.0724 0.032 Uiso 1 1 calc R . .
C6 C 0.5670(3) 0.25890(15) 0.02854(14) 0.0243(6) Uani 1 1 d . . .
C7 C 0.4184(3) 0.23243(15) 0.05532(14) 0.0258(6) Uani 1 1 d . . .
H7 H 0.3488 0.1949 0.0230 0.031 Uiso 1 1 calc R . .
C8 C 0.3640(3) 0.25438(16) 0.12167(15) 0.0268(6) Uani 1 1 d . . .
H8 H 0.4318 0.2913 0.1556 0.032 Uiso 1 1 calc R . .
C9 C 0.2095(3) 0.22503(16) 0.14360(15) 0.0273(6) Uani 1 1 d . . .
C10 C 0.1612(4) 0.25253(17) 0.21282(16) 0.0323(6) Uani 1 1 d . . .
H10 H 0.2335 0.2885 0.2460 0.039 Uiso 1 1 calc R . .
C11 C 0.0106(4) 0.22783(17) 0.23277(17) 0.0352(7) Uani 1 1 d . . .
H11 H -0.0213 0.2481 0.2789 0.042 Uiso 1 1 calc R . .
C12 C 0.0978(3) 0.16996(16) 0.09922(16) 0.0296(6) Uani 1 1 d . . .
H12 H 0.1253 0.1489 0.0525 0.035 Uiso 1 1 calc R . .
C13 C -0.0499(3) 0.14608(17) 0.12202(16) 0.0331(7) Uani 1 1 d . . .
H13 H -0.1229 0.1086 0.0911 0.040 Uiso 1 1 calc R . .
C14 C -0.2563(4) 0.1506(2) 0.2095(2) 0.0463(9) Uani 1 1 d . . .
H14A H -0.2396 0.1006 0.2395 0.069 Uiso 1 1 calc R . .
H14B H -0.3420 0.1422 0.1621 0.069 Uiso 1 1 calc R . .
H14C H -0.2957 0.1926 0.2413 0.069 Uiso 1 1 calc R . .
S2 S 1.1186(3) 0.14818(11) 0.83711(11) 0.0218(4) Uani 0.50 1 d PDU A 1
O1 O 1.2881(6) 0.1489(3) 0.8138(2) 0.0285(9) Uani 0.50 1 d PDU A 1
O2 O 1.0204(5) 0.2213(2) 0.8169(2) 0.0261(8) Uani 0.50 1 d PDU A 1
O3 O 1.1230(7) 0.1275(3) 0.9193(2) 0.0314(11) Uani 0.50 1 d PDU A 1
N3 N 0.7676(8) 0.0762(4) 0.8597(4) 0.0284(17) Uani 0.50 1 d PD A 1
H3A H 0.6542(16) 0.084(3) 0.849(3) 0.027(16) Uiso 0.50 1 d PD B 1
H3B H 0.828(5) 0.1197(19) 0.878(3) 0.02(2) Uiso 0.50 1 d PD C 1
C15 C 0.5844(9) -0.0457(4) 0.7676(4) 0.0292(15) Uani 0.50 1 d PDU A 1
H15A H 0.5393 -0.0876 0.7299 0.044 Uiso 0.50 1 calc PR A 1
H15B H 0.5031 -0.0011 0.7632 0.044 Uiso 0.50 1 calc PR A 1
H15C H 0.6015 -0.0679 0.8205 0.044 Uiso 0.50 1 calc PR A 1
C16 C 0.7500(6) -0.0165(3) 0.7512(3) 0.0250(16) Uani 0.50 1 d PGDU A 1
C17 C 0.8165(10) -0.0488(4) 0.6897(4) 0.034(2) Uani 0.50 1 d PGDU A 1
H17A H 0.7559 -0.0897 0.6581 0.040 Uiso 0.50 1 calc PR A 1
C18 C 0.9719(11) -0.0214(5) 0.6745(4) 0.026(3) Uani 0.50 1 d PGDU A 1
C20 C 1.0606(7) 0.0384(4) 0.7207(4) 0.0242(19) Uani 0.50 1 d PGDU A 1
H20A H 1.1667 0.0571 0.7103 0.029 Uiso 0.50 1 calc PR A 1
C21 C 0.9940(6) 0.0708(2) 0.7822(3) 0.0219(14) Uani 0.50 1 d PGDU A 1
C22 C 0.8387(6) 0.0433(2) 0.7974(2) 0.0247(14) Uani 0.50 1 d PGDU A 1
C19 C 1.039(3) -0.0587(10) 0.6056(6) 0.037(5) Uani 0.50 1 d PDU A 1
H19A H 0.9576 -0.0993 0.5807 0.055 Uiso 0.50 1 calc PR A 1
H19B H 1.1498 -0.0837 0.6245 0.055 Uiso 0.50 1 calc PR A 1
H19C H 1.0507 -0.0168 0.5676 0.055 Uiso 0.50 1 calc PR A 1
S2' S 1.1912(3) 0.13929(12) 0.83914(13) 0.0282(5) Uani 0.50 1 d PDU D 2
O1' O 1.3556(6) 0.1244(3) 0.8165(3) 0.0396(14) Uani 0.50 1 d PDU D 2
O2' O 1.1174(6) 0.2181(3) 0.8175(3) 0.0384(11) Uani 0.50 1 d PDU D 2
O3' O 1.1950(6) 0.1218(3) 0.9226(3) 0.0311(14) Uani 0.50 1 d PDU D 2
N3' N 0.8419(9) 0.0846(5) 0.8754(4) 0.0350(18) Uani 0.50 1 d PD D 2
H3A' H 0.933(4) 0.107(3) 0.906(2) 0.028(16) Uiso 0.50 1 d PD E 2
H3B' H 0.764(6) 0.065(5) 0.902(3) 0.08(3) Uiso 0.50 1 d PD F 2
C15' C 0.6074(11) -0.0266(4) 0.7893(4) 0.038(2) Uani 0.50 1 d PDU D 2
H15D H 0.5454 -0.0654 0.7523 0.057 Uiso 0.50 1 calc PR D 2
H15E H 0.5382 0.0219 0.7897 0.057 Uiso 0.50 1 calc PR D 2
H15F H 0.6303 -0.0502 0.8417 0.057 Uiso 0.50 1 calc PR D 2
C16' C 0.7796(6) -0.0046(3) 0.7644(3) 0.0238(17) Uani 0.50 1 d PGDU D 2
C17' C 0.8233(9) -0.0391(4) 0.6983(3) 0.0188(17) Uani 0.50 1 d PGDU D 2
H17B H 0.7481 -0.0762 0.6681 0.023 Uiso 0.50 1 calc PR D 2
C18' C 0.9771(10) -0.0192(5) 0.6762(4) 0.024(3) Uani 0.50 1 d PGDU D 2
C20' C 1.0872(7) 0.0351(4) 0.7204(4) 0.0193(18) Uani 0.50 1 d PGDU D 2
H20B H 1.1923 0.0487 0.7053 0.023 Uiso 0.50 1 calc PR D 2
C21' C 1.0435(6) 0.0696(3) 0.7866(3) 0.0176(15) Uani 0.50 1 d PGDU D 2
C22' C 0.8897(6) 0.0497(3) 0.8086(2) 0.0244(16) Uani 0.50 1 d PGDU D 2
C19' C 1.029(3) -0.0550(11) 0.6040(7) 0.037(5) Uani 0.50 1 d PDU D 2
H19D H 1.1404 -0.0336 0.5982 0.056 Uiso 0.50 1 calc PR D 2
H19E H 0.9435 -0.0411 0.5579 0.056 Uiso 0.50 1 calc PR D 2
H19F H 1.0362 -0.1135 0.6093 0.056 Uiso 0.50 1 calc PR D 2
O4 O 0.3191(4) -0.01280(16) -0.00866(15) 0.0612(7) Uani 0.95 1 d P G 1
O4' O 0.5000 0.0000 0.0000 0.038(7) Uani 0.10 2 d SP H 2

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 0.0323(4) 0.0252(4) 0.0243(4) -0.0016(2) 0.0074(3) 0.0011(3)
N1 0.0363(14) 0.0391(14) 0.0380(14) -0.0096(11) 0.0131(11) -0.0108(11)
N2 0.0266(13) 0.0408(14) 0.0369(14) 0.0159(11) 0.0106(11) 0.0128(11)
C1 0.0315(16) 0.0349(15) 0.0359(16) 0.0056(12) 0.0084(13) -0.0006(12)
C2 0.0471(18) 0.0331(15) 0.0418(17) -0.0078(13) 0.0099(14) -0.0123(14)
C3 0.0287(15) 0.0256(13) 0.0265(14) 0.0040(10) 0.0063(11) 0.0012(11)
C4 0.0283(14) 0.0294(14) 0.0214(13) 0.0006(10) 0.0058(11) 0.0031(11)
C5 0.0269(14) 0.0292(14) 0.0225(13) -0.0003(11) 0.0016(11) 0.0034(11)
C6 0.0262(14) 0.0239(13) 0.0223(13) 0.0026(10) 0.0036(11) 0.0061(10)
C7 0.0245(14) 0.0292(14) 0.0223(13) 0.0030(10) 0.0002(11) 0.0048(11)
C8 0.0247(14) 0.0299(14) 0.0250(14) 0.0015(11) 0.0031(11) 0.0036(11)
C9 0.0250(14) 0.0305(14) 0.0255(14) 0.0069(11) 0.0023(11) 0.0093(11)
C10 0.0349(16) 0.0343(15) 0.0289(15) 0.0043(12) 0.0091(12) 0.0079(12)
C11 0.0387(17) 0.0388(16) 0.0311(15) 0.0103(12) 0.0142(13) 0.0139(13)
C12 0.0266(15) 0.0366(15) 0.0258(14) 0.0042(11) 0.0057(12) 0.0055(12)
C13 0.0280(15) 0.0360(15) 0.0344(16) 0.0085(12) 0.0035(12) 0.0058(12)
C14 0.0261(16) 0.059(2) 0.058(2) 0.0256(17) 0.0175(15) 0.0115(14)
S2 0.0216(10) 0.0241(8) 0.0194(8) -0.0015(5) 0.0036(8) -0.0024(8)
O1 0.018(2) 0.036(2) 0.034(2) -0.0093(18) 0.011(2) -0.006(2)
O2 0.027(2) 0.0222(18) 0.030(2) -0.0030(14) 0.0087(18) 0.0000(16)
O3 0.034(3) 0.042(2) 0.016(2) 0.0000(16) -0.001(2) 0.001(2)
N3 0.025(4) 0.031(3) 0.032(3) -0.009(2) 0.011(3) -0.005(3)
C15 0.028(3) 0.035(3) 0.026(3) -0.009(3) 0.008(3) 0.000(3)
C16 0.019(3) 0.018(3) 0.034(3) 0.007(2) -0.005(2) -0.004(2)
C17 0.038(4) 0.029(3) 0.031(3) 0.000(2) -0.003(3) 0.000(3)
C18 0.030(4) 0.027(4) 0.020(4) 0.001(2) -0.001(2) 0.003(2)
C20 0.015(3) 0.027(3) 0.030(3) 0.012(2) 0.003(2) 0.002(2)
C21 0.019(3) 0.022(3) 0.026(3) 0.000(2) 0.006(2) -0.005(2)
C22 0.020(3) 0.024(3) 0.034(3) 0.005(2) 0.016(2) 0.003(2)
C19 0.053(8) 0.037(6) 0.024(5) -0.011(3) 0.016(3) -0.011(3)
S2' 0.0302(10) 0.0265(7) 0.0270(7) -0.0031(5) 0.0031(8) -0.0029(8)
O1' 0.0391(16) 0.0403(16) 0.0396(16) -0.0012(9) 0.0076(10) -0.0013(9)
O2' 0.0398(14) 0.0362(14) 0.0387(14) 0.0002(9) 0.0061(10) -0.0004(10)
O3' 0.0316(17) 0.0321(16) 0.0297(16) -0.0004(9) 0.0063(10) -0.0002(10)
N3' 0.032(5) 0.031(4) 0.045(4) -0.007(3) 0.016(4) -0.010(4)
C15' 0.038(2) 0.038(2) 0.039(2) -0.0001(10) 0.0068(11) 0.0003(10)
C16' 0.0234(19) 0.0237(19) 0.0243(19) 0.0012(10) 0.0045(10) -0.0007(10)
C17' 0.0186(19) 0.0187(18) 0.0185(18) -0.0002(10) 0.0021(10) -0.0014(10)
C18' 0.023(3) 0.024(3) 0.024(3) 0.0004(10) 0.0048(11) 0.0000(10)
C20' 0.0196(19) 0.019(2) 0.019(2) -0.0004(10) 0.0035(10) 0.0016(10)
C21' 0.0171(17) 0.0180(17) 0.0179(17) 0.0001(9) 0.0033(9) 0.0003(9)
C22' 0.0250(19) 0.0232(18) 0.0247(18) -0.0002(9) 0.0040(10) -0.0001(10)
C19' 0.038(5) 0.037(5) 0.037(5) -0.0001(10) 0.0071(13) -0.0002(10)
O4 0.0685(18) 0.0666(17) 0.0523(16) 0.0030(13) 0.0213(13) -0.0170(14)
O4' 0.028(16) 0.046(17) 0.039(16) 0.002(13) 0.003(12) 0.026(13)

_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 1.740(3) . ?
S1 C6 1.748(3) . ?
N1 C3 1.360(3) . ?
N1 C2 1.445(3) . ?
N1 C1 1.450(4) . ?
N2 C11 1.347(4) . ?
N2 C13 1.350(4) . ?
N2 C14 1.480(4) . ?
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 1.381(4) . ?
C4 C5 1.406(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(4) . ?
C7 C8 1.359(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.440(4) . ?
C8 H8 0.9500 . ?
C9 C12 1.407(4) . ?
C9 C10 1.410(4) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.368(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S2 O2 1.457(4) . ?
S2 O3 1.468(4) . ?
S2 O1 1.481(4) . ?
S2 C21 1.794(5) . ?
N3 C22 1.424(6) . ?
N3 H3A 0.897(10) . ?
N3 H3B 0.894(10) . ?
C15 C16 1.483(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3900 . ?
C16 C22 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17A 0.9500 . ?
C18 C20 1.3900 . ?
C18 C19 1.532(8) . ?
C20 C21 1.3900 . ?
C20 H20A 0.9500 . ?
C21 C22 1.3900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S2' O1' 1.457(5) . ?
S2' O2' 1.460(5) . ?
S2' O3' 1.479(5) . ?
S2' C21' 1.782(5) . ?
N3' C22' 1.416(7) . ?
N3' H3A' 0.899(10) . ?
N3' H3B' 0.900(10) . ?
C15' C16' 1.557(10) . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' C17' 1.3900 . ?
C16' C22' 1.3900 . ?
C17' C18' 1.3900 . ?
C17' H17B 0.9500 . ?
C18' C20' 1.3900 . ?
C18' C19' 1.519(11) . ?
C20' C21' 1.3900 . ?
C20' H20B 0.9500 . ?
C21' C22' 1.3900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 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 91.45(12) . . ?
C3 N1 C2 121.3(2) . . ?
C3 N1 C1 119.2(2) . . ?
C2 N1 C1 119.4(2) . . ?
C11 N2 C13 120.3(2) . . ?
C11 N2 C14 120.4(3) . . ?
C13 N2 C14 119.3(3) . . ?
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 127.8(2) . . ?
N1 C3 S1 120.5(2) . . ?
C4 C3 S1 111.6(2) . . ?
C3 C4 C5 112.1(2) . . ?
C3 C4 H4 124.0 . . ?
C5 C4 H4 124.0 . . ?
C6 C5 C4 114.6(2) . . ?
C6 C5 H5 122.7 . . ?
C4 C5 H5 122.7 . . ?
C5 C6 C7 126.5(2) . . ?
C5 C6 S1 110.25(19) . . ?
C7 C6 S1 123.21(19) . . ?
C8 C7 C6 127.8(3) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C7 C8 C9 123.9(3) . . ?
C7 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C12 C9 C10 116.0(2) . . ?
C12 C9 C8 124.1(2) . . ?
C10 C9 C8 119.9(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N2 C11 C10 121.1(3) . . ?
N2 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C9 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C9 C12 H12 119.3 . . ?
N2 C13 C12 120.6(3) . . ?
N2 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
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 . . ?
O2 S2 O3 110.4(3) . . ?
O2 S2 O1 113.8(3) . . ?
O3 S2 O1 114.3(3) . . ?
O2 S2 C21 104.7(2) . . ?
O3 S2 C21 105.2(3) . . ?
O1 S2 C21 107.6(3) . . ?
C22 N3 H3A 115(3) . . ?
C22 N3 H3B 109(4) . . ?
H3A N3 H3B 114.0(18) . . ?
C22 N3 H3A' 96(2) . . ?
H3A N3 H3A' 144(4) . . ?
H3B N3 H3A' 34(4) . . ?
C22 N3 H3B' 137(7) . . ?
H3A N3 H3B' 91(5) . . ?
H3B N3 H3B' 88(6) . . ?
H3A' N3 H3B' 75.2(17) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C22 120.0 . . ?
C17 C16 C15 120.1(5) . . ?
C22 C16 C15 119.9(5) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C20 120.0 . . ?
C17 C18 C19 117.8(10) . . ?
C20 C18 C19 122.2(10) . . ?
C18 C20 C21 120.0 . . ?
C18 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 S2 116.0(4) . . ?
C22 C21 S2 124.0(4) . . ?
C21 C22 C16 120.0 . . ?
C21 C22 N3 120.9(5) . . ?
C16 C22 N3 119.1(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1' S2' O2' 115.0(3) . . ?
O1' S2' O3' 112.2(3) . . ?
O2' S2' O3' 111.4(3) . . ?
O1' S2' C21' 106.9(3) . . ?
O2' S2' C21' 105.0(3) . . ?
O3' S2' C21' 105.6(3) . . ?
C22' N3' H3A 99(2) . . ?
C22' N3' H3B 123(6) . . ?
H3A N3' H3B 80(2) . . ?
C22' N3' H3A' 111(3) . . ?
H3A N3' H3A' 147(4) . . ?
H3B N3' H3A' 72(5) . . ?
C22' N3' H3B' 126(5) . . ?
H3A N3' H3B' 53(5) . . ?
H3B N3' H3B' 99(8) . . ?
H3A' N3' H3B' 113.1(18) . . ?
C16' C15' H15D 109.5 . . ?
C16' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C16' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C17' C16' C22' 120.0 . . ?
C17' C16' C15' 120.2(5) . . ?
C22' C16' C15' 119.8(5) . . ?
C16' C17' C18' 120.0 . . ?
C16' C17' H17B 120.0 . . ?
C18' C17' H17B 120.0 . . ?
C17' C18' C20' 120.0 . . ?
C17' C18' C19' 121.6(10) . . ?
C20' C18' C19' 118.4(10) . . ?
C21' C20' C18' 120.0 . . ?
C21' C20' H20B 120.0 . . ?
C18' C20' H20B 120.0 . . ?
C20' C21' C22' 120.0 . . ?
C20' C21' S2' 117.0(4) . . ?
C22' C21' S2' 123.0(4) . . ?
C21' C22' C16' 120.0 . . ?
C21' C22' N3' 121.0(5) . . ?
C16' C22' N3' 119.0(5) . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 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 177.1(3) . . . . ?
C1 N1 C3 C4 1.4(4) . . . . ?
C2 N1 C3 S1 -4.1(4) . . . . ?
C1 N1 C3 S1 -179.9(2) . . . . ?
C6 S1 C3 N1 -177.6(2) . . . . ?
C6 S1 C3 C4 1.4(2) . . . . ?
N1 C3 C4 C5 177.8(3) . . . . ?
S1 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 S1 0.9(3) . . . . ?
C3 S1 C6 C5 -1.28(19) . . . . ?
C3 S1 C6 C7 177.7(2) . . . . ?
C5 C6 C7 C8 177.3(3) . . . . ?
S1 C6 C7 C8 -1.6(4) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C7 C8 C9 C12 0.4(4) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C12 C9 C10 C11 -2.0(4) . . . . ?
C8 C9 C10 C11 177.1(2) . . . . ?
C13 N2 C11 C10 -0.3(4) . . . . ?
C14 N2 C11 C10 -178.8(2) . . . . ?
C9 C10 C11 N2 1.7(4) . . . . ?
C10 C9 C12 C13 1.0(4) . . . . ?
C8 C9 C12 C13 -178.1(2) . . . . ?
C11 N2 C13 C12 -0.7(4) . . . . ?
C14 N2 C13 C12 177.8(2) . . . . ?
C9 C12 C13 N2 0.3(4) . . . . ?
C22 C16 C17 C18 0.0 . . . . ?
C15 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C20 0.0 . . . . ?
C16 C17 C18 C19 -179.5(2) . . . . ?
C17 C18 C20 C21 0.0 . . . . ?
C19 C18 C20 C21 179.5(2) . . . . ?
C18 C20 C21 C22 0.0 . . . . ?
C18 C20 C21 S2 -179.38(18) . . . . ?
O2 S2 C21 C20 109.6(3) . . . . ?
O3 S2 C21 C20 -134.0(3) . . . . ?
O1 S2 C21 C20 -11.8(3) . . . . ?
O2 S2 C21 C22 -69.8(3) . . . . ?
O3 S2 C21 C22 46.6(3) . . . . ?
O1 S2 C21 C22 168.9(3) . . . . ?
C20 C21 C22 C16 0.0 . . . . ?
S2 C21 C22 C16 179.33(19) . . . . ?
C20 C21 C22 N3 -179.4(2) . . . . ?
S2 C21 C22 N3 -0.1(3) . . . . ?
C17 C16 C22 C21 0.0 . . . . ?
C15 C16 C22 C21 179.9(2) . . . . ?
C17 C16 C22 N3 179.5(2) . . . . ?
C15 C16 C22 N3 -0.7(3) . . . . ?
C22' C16' C17' C18' 0.0 . . . . ?
C15' C16' C17' C18' 179.9(2) . . . . ?
C16' C17' C18' C20' 0.0 . . . . ?
C16' C17' C18' C19' -179.5(2) . . . . ?
C17' C18' C20' C21' 0.0 . . . . ?
C19' C18' C20' C21' 179.5(2) . . . . ?
C18' C20' C21' C22' 0.0 . . . . ?
C18' C20' C21' S2' -179.41(18) . . . . ?
O1' S2' C21' C20' -19.7(3) . . . . ?
O2' S2' C21' C20' 102.8(3) . . . . ?
O3' S2' C21' C20' -139.3(3) . . . . ?
O1' S2' C21' C22' 160.9(3) . . . . ?
O2' S2' C21' C22' -76.6(3) . . . . ?
O3' S2' C21' C22' 41.3(3) . . . . ?
C20' C21' C22' C16' 0.0 . . . . ?
S2' C21' C22' C16' 179.4(2) . . . . ?
C20' C21' C22' N3' -179.4(3) . . . . ?
S2' C21' C22' N3' -0.1(3) . . . . ?
C17' C16' C22' C21' 0.0 . . . . ?
C15' C16' C22' C21' -179.9(2) . . . . ?
C17' C16' C22' N3' 179.4(2) . . . . ?
C15' C16' C22' N3' -0.5(3) . . . . ?

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
N3 H3B O3 0.894(10) 2.33(4) 2.955(8) 127(4) .
N3 H3B S2 0.894(10) 2.59(5) 3.134(7) 120(4) .
N3 H3B O2 0.894(10) 2.64(5) 3.321(8) 134(5) .
N3' H3A' O3' 0.899(10) 2.07(3) 2.849(9) 144(5) .
N3' H3A' S2' 0.899(10) 2.61(5) 3.103(8) 115(4) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.057