# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010


data_wheeler
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef 'web_deposit_cif_file_0_KraigA.Wheeler_1281139506.cif'

#===================================================================

_audit_creation_method           'from SHELXL97 CIF, local template and enCIFer'
#===================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name        'Dr. Kraig A. Wheeler'

_publ_contact_author_address     
;
Eastern Illinios University
Department of Chemistry
600 Lincoln Avenue
Charleston, IL 61920
;

_publ_contact_author_email       kawheeler@eiu.edu
_publ_contact_author_fax         217-581-6613
_publ_contact_author_phone       217-581-3119

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
K.A.Wheeler
;
Eastern Illinios University
Department of Chemistry
600 Lincoln Avenue
Charleston, IL 61920-3099
;
?
'Joshua D. Wiseman'
;
Eastern Illinios University
Department of Chemistry
600 Lincoln Avenue
Charleston, IL 61920-3099
;
?
R.Grove
;
Eastern Illinios University
Department of Chemistry
600 Lincoln Avenue
Charleston, IL 61920-3099
;
?
#===================================================================

data_kaw47b
_database_code_depnum_ccdc_archive 'CCDC 787768'
#TrackingRef 'web_deposit_cif_file_0_KraigA.Wheeler_1281139506.cif'

# unreacted 3-I

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N O6 S'
_chemical_formula_sum            'C12 H13 N O6 S'
_chemical_formula_weight         299.30
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.1020(2)
_cell_length_b                   8.0330(2)
_cell_length_c                   11.9154(3)
_cell_angle_alpha                95.252(1)
_cell_angle_beta                 104.650(1)
_cell_angle_gamma                99.577(1)
_cell_volume                     642.12(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6355
_cell_measurement_theta_min      3.547
_cell_measurement_theta_max      69.022

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    2.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   'SADABS (Bruker, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11522
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         68.23
_reflns_number_total             3910
_reflns_number_gt                3829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2009)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_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.

All Non-hydrogen atoms were located in Fourier difference density maps and
refined using anisotropic displacement parameters. Acidic H atoms (O-H
and N-H) were also located in difference maps and refined isotropically
with bonds constrained to 0.85(1) angstroms. All other H atoms were
placed in calculated positions and refined with Ueq = 1.2Uiso of the
corresponding atom (1.5Uiso for methyl groups).
;

_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^)+(0.0477P)^2^+0.2295P] 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   0.037(14)
_refine_ls_number_reflns         3910
_refine_ls_number_parameters     388
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.066
_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
S1A S 0.03619(9) 0.37761(7) 0.60993(5) 0.02185(15) Uani 1 1 d . . .
O1A O 0.6776(3) 1.2435(3) 1.21147(19) 0.0286(4) Uani 1 1 d D . .
O2A O 0.4908(3) 1.3627(3) 1.07297(19) 0.0317(5) Uani 1 1 d . . .
O3A O 0.5876(3) 0.6632(2) 0.65213(16) 0.0244(4) Uani 1 1 d D . .
O4A O 0.3516(3) 0.7495(2) 0.52052(16) 0.0247(4) Uani 1 1 d . . .
O5A O 0.1214(3) 0.2455(2) 0.66534(18) 0.0298(5) Uani 1 1 d . . .
O6A O -0.1738(3) 0.3563(3) 0.56321(18) 0.0296(4) Uani 1 1 d . . .
N1A N 0.1281(3) 0.4099(3) 0.49969(18) 0.0215(4) Uani 1 1 d D . .
C1A C 0.5492(4) 1.2347(4) 1.1120(3) 0.0240(6) Uani 1 1 d . . .
H13A H 0.715(11) 1.339(5) 1.256(5) 0.15(3) Uiso 1 1 d D . .
H14A H 0.639(6) 0.764(3) 0.689(4) 0.069(14) Uiso 1 1 d D . .
H15A H 0.059(4) 0.465(4) 0.453(2) 0.039(9) Uiso 1 1 d D . .
H13B H 0.448(6) 0.980(3) 0.584(3) 0.061(13) Uiso 1 1 d D . .
H14B H 0.594(8) 1.574(3) 1.150(4) 0.093(18) Uiso 1 1 d D . .
H15B H 0.847(4) 2.042(3) 1.242(2) 0.025(8) Uiso 1 1 d D . .
C2A C 0.4784(4) 1.0643(3) 1.0439(3) 0.0243(6) Uani 1 1 d . . .
H2A H 0.5233 0.9700 1.0770 0.029 Uiso 1 1 calc R . .
C3A C 0.3539(4) 1.0374(4) 0.9378(3) 0.0244(6) Uani 1 1 d . . .
H3A H 0.3111 1.1341 0.9073 0.029 Uiso 1 1 calc R . .
C4A C 0.2757(4) 0.8726(4) 0.8626(2) 0.0217(6) Uani 1 1 d . . .
C5A C 0.3354(4) 0.7216(4) 0.8950(3) 0.0237(6) Uani 1 1 d . . .
H5A H 0.4274 0.7238 0.9688 0.028 Uiso 1 1 calc R . .
C6A C 0.2602(4) 0.5691(4) 0.8196(3) 0.0227(6) Uani 1 1 d . . .
H6A H 0.3016 0.4672 0.8412 0.027 Uiso 1 1 calc R . .
C7A C 0.1247(4) 0.5666(4) 0.7127(2) 0.0210(6) Uani 1 1 d . . .
C8A C 0.0610(4) 0.7148(4) 0.6802(2) 0.0233(6) Uani 1 1 d . . .
H8A H -0.0344 0.7109 0.6075 0.028 Uiso 1 1 calc R . .
C9A C 0.1369(4) 0.8670(3) 0.7542(2) 0.0232(6) Uani 1 1 d . . .
H9A H 0.0952 0.9683 0.7317 0.028 Uiso 1 1 calc R . .
C10A C 0.4292(4) 0.6365(3) 0.5658(2) 0.0193(5) Uani 1 1 d . . .
C11A C 0.3431(4) 0.4491(3) 0.5174(2) 0.0198(5) Uani 1 1 d . . .
H11A H 0.4059 0.3772 0.5745 0.024 Uiso 1 1 calc R . .
C12A C 0.3913(5) 0.4071(4) 0.4015(2) 0.0278(6) Uani 1 1 d . . .
H12A H 0.3495 0.2843 0.3748 0.042 Uiso 1 1 calc R . .
H12B H 0.5346 0.4409 0.4125 0.042 Uiso 1 1 calc R . .
H12C H 0.3208 0.4692 0.3426 0.042 Uiso 1 1 calc R . .
S1B S 1.09860(8) 1.98223(7) 1.19890(5) 0.02008(15) Uani 1 1 d . . .
O1B O 0.4907(3) 1.0790(3) 0.62431(18) 0.0297(5) Uani 1 1 d D . .
O2B O 0.7095(3) 0.9760(3) 0.75697(19) 0.0305(5) Uani 1 1 d . . .
O3B O 0.6445(3) 1.6727(3) 1.18908(17) 0.0249(4) Uani 1 1 d D . .
O4B O 0.8371(3) 1.5531(2) 1.32474(15) 0.0240(4) Uani 1 1 d . . .
O5B O 1.0835(3) 2.1214(2) 1.13247(17) 0.0276(4) Uani 1 1 d . . .
O6B O 1.2829(3) 1.9763(2) 1.28159(18) 0.0275(4) Uani 1 1 d . . .
N1B N 0.9286(3) 1.9802(3) 1.26646(19) 0.0231(5) Uani 1 1 d D . .
C1B C 0.6313(4) 1.0965(4) 0.7211(2) 0.0222(6) Uani 1 1 d . . .
C2B C 0.6917(4) 1.2692(4) 0.7865(3) 0.0252(6) Uani 1 1 d . . .
H2B H 0.6293 1.3569 0.7551 0.030 Uiso 1 1 calc R . .
C3B C 0.8317(4) 1.3072(3) 0.8889(2) 0.0215(6) Uani 1 1 d . . .
H3B H 0.8920 1.2170 0.9179 0.026 Uiso 1 1 calc R . .
C4B C 0.9013(4) 1.4764(4) 0.9611(3) 0.0209(6) Uani 1 1 d . . .
C5B C 0.8249(4) 1.6191(4) 0.9256(2) 0.0212(5) Uani 1 1 d . . .
H5B H 0.7281 1.6083 0.8525 0.025 Uiso 1 1 calc R . .
C6B C 0.8888(4) 1.7749(3) 0.9957(2) 0.0214(6) Uani 1 1 d . . .
H6B H 0.8361 1.8711 0.9718 0.026 Uiso 1 1 calc R . .
C7B C 1.0314(4) 1.7891(3) 1.1020(2) 0.0205(6) Uani 1 1 d . . .
C8B C 1.1131(4) 1.6502(3) 1.1374(2) 0.0219(6) Uani 1 1 d . . .
H8B H 1.2129 1.6624 1.2094 0.026 Uiso 1 1 calc R . .
C9B C 1.0471(4) 1.4938(3) 1.0662(2) 0.0232(6) Uani 1 1 d . . .
H9B H 1.1020 1.3983 1.0895 0.028 Uiso 1 1 calc R . .
C10B C 0.7859(4) 1.6818(3) 1.2813(2) 0.0212(5) Uani 1 1 d . . .
C11B C 0.8952(4) 1.8574(3) 1.3450(2) 0.0216(5) Uani 1 1 d . . .
H11B H 1.0263 1.8470 1.3969 0.026 Uiso 1 1 calc R . .
C12B C 0.7689(5) 1.9221(4) 1.4221(2) 0.0279(6) Uani 1 1 d . . .
H12D H 0.8428 2.0294 1.4710 0.042 Uiso 1 1 calc R . .
H12E H 0.7397 1.8368 1.4722 0.042 Uiso 1 1 calc R . .
H12F H 0.6443 1.9412 1.3716 0.042 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
S1A 0.0243(3) 0.0159(3) 0.0245(3) 0.0032(2) 0.0068(3) 0.0012(3)
O1A 0.0271(11) 0.0229(10) 0.0322(11) -0.0023(8) 0.0031(9) 0.0058(9)
O2A 0.0293(11) 0.0219(10) 0.0442(13) 0.0068(10) 0.0084(9) 0.0075(9)
O3A 0.0242(10) 0.0186(9) 0.0249(9) -0.0002(7) -0.0013(7) 0.0027(8)
O4A 0.0244(10) 0.0181(9) 0.0276(9) 0.0033(8) 0.0006(7) 0.0028(8)
O5A 0.0389(12) 0.0166(9) 0.0342(10) 0.0074(8) 0.0096(9) 0.0045(9)
O6A 0.0247(10) 0.0274(10) 0.0338(11) 0.0022(8) 0.0079(8) -0.0019(9)
N1A 0.0199(11) 0.0166(11) 0.0240(11) 0.0028(8) 0.0003(8) 0.0016(9)
C1A 0.0188(14) 0.0247(14) 0.0281(15) 0.0039(12) 0.0067(11) 0.0021(12)
C2A 0.0261(14) 0.0181(14) 0.0301(15) 0.0033(11) 0.0103(12) 0.0043(12)
C3A 0.0216(14) 0.0227(14) 0.0324(16) 0.0096(12) 0.0102(12) 0.0067(12)
C4A 0.0191(13) 0.0201(13) 0.0265(14) 0.0035(11) 0.0075(11) 0.0032(11)
C5A 0.0198(13) 0.0252(14) 0.0253(14) 0.0071(12) 0.0038(11) 0.0041(12)
C6A 0.0226(14) 0.0191(13) 0.0279(14) 0.0067(11) 0.0070(11) 0.0066(12)
C7A 0.0221(14) 0.0164(13) 0.0255(14) 0.0041(11) 0.0088(11) 0.0025(11)
C8A 0.0247(14) 0.0244(14) 0.0229(13) 0.0070(11) 0.0066(11) 0.0083(12)
C9A 0.0237(14) 0.0206(13) 0.0281(14) 0.0083(11) 0.0078(11) 0.0085(11)
C10A 0.0204(13) 0.0204(13) 0.0181(12) 0.0014(10) 0.0073(10) 0.0047(11)
C11A 0.0213(12) 0.0180(12) 0.0183(11) 0.0021(9) 0.0036(9) 0.0019(10)
C12A 0.0299(14) 0.0264(14) 0.0258(14) -0.0006(12) 0.0078(11) 0.0033(13)
S1B 0.0222(3) 0.0144(3) 0.0221(3) 0.0009(2) 0.0053(2) 0.0014(3)
O1B 0.0299(11) 0.0248(11) 0.0275(10) 0.0001(9) -0.0001(9) 0.0004(9)
O2B 0.0297(11) 0.0199(10) 0.0392(11) 0.0026(8) 0.0042(9) 0.0067(9)
O3B 0.0257(10) 0.0249(10) 0.0204(9) 0.0036(8) -0.0004(8) 0.0045(9)
O4B 0.0258(10) 0.0205(9) 0.0235(9) 0.0054(7) 0.0027(7) 0.0033(8)
O5B 0.0368(12) 0.0167(9) 0.0296(10) 0.0028(8) 0.0109(9) 0.0031(9)
O6B 0.0218(10) 0.0226(9) 0.0327(10) -0.0020(8) 0.0032(8) -0.0007(8)
N1B 0.0263(12) 0.0176(10) 0.0255(10) 0.0046(8) 0.0052(9) 0.0071(9)
C1B 0.0211(13) 0.0204(14) 0.0246(14) 0.0032(11) 0.0064(11) 0.0022(12)
C2B 0.0235(14) 0.0198(14) 0.0311(15) 0.0040(12) 0.0052(11) 0.0042(12)
C3B 0.0203(13) 0.0148(12) 0.0290(14) 0.0028(11) 0.0063(11) 0.0030(11)
C4B 0.0193(13) 0.0180(13) 0.0278(14) 0.0070(11) 0.0091(11) 0.0042(11)
C5B 0.0194(13) 0.0218(13) 0.0212(13) 0.0036(11) 0.0029(10) 0.0047(11)
C6B 0.0218(14) 0.0174(13) 0.0273(14) 0.0075(11) 0.0074(11) 0.0065(11)
C7B 0.0215(14) 0.0147(13) 0.0254(14) 0.0041(11) 0.0066(11) 0.0030(11)
C8B 0.0211(14) 0.0189(13) 0.0242(13) 0.0059(10) 0.0023(10) 0.0041(11)
C9B 0.0237(14) 0.0179(12) 0.0287(14) 0.0076(11) 0.0049(11) 0.0071(11)
C10B 0.0201(13) 0.0193(13) 0.0267(13) 0.0054(11) 0.0091(10) 0.0054(11)
C11B 0.0187(12) 0.0217(13) 0.0216(12) 0.0032(10) 0.0028(10) 0.0000(11)
C12B 0.0341(16) 0.0274(15) 0.0222(13) -0.0023(11) 0.0115(11) 0.0031(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
S1A O6A 1.429(2) . ?
S1A O5A 1.4380(19) . ?
S1A N1A 1.630(2) . ?
S1A C7A 1.775(3) . ?
O1A C1A 1.287(4) . ?
O1A H13A 0.85(5) . ?
O2A C1A 1.256(3) . ?
O3A C10A 1.290(3) . ?
O3A H14A 0.86(3) . ?
O4A C10A 1.234(3) . ?
N1A C11A 1.463(3) . ?
N1A H15A 0.85(3) . ?
C1A C2A 1.466(4) . ?
C2A C3A 1.322(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.466(4) . ?
C3A H3A 0.9500 . ?
C4A C9A 1.404(4) . ?
C4A C5A 1.405(4) . ?
C5A C6A 1.390(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.385(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.395(3) . ?
C8A C9A 1.381(4) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.526(3) . ?
C11A C12A 1.527(4) . ?
C11A H11A 1.0000 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
S1B O5B 1.4307(19) . ?
S1B O6B 1.436(2) . ?
S1B N1B 1.611(2) . ?
S1B C7B 1.765(3) . ?
O1B C1B 1.300(3) . ?
O1B H13B 0.86(3) . ?
O2B C1B 1.250(3) . ?
O3B C10B 1.274(3) . ?
O3B H14B 0.85(3) . ?
O4B C10B 1.263(3) . ?
N1B C11B 1.452(3) . ?
N1B H15B 0.84(3) . ?
C1B C2B 1.466(4) . ?
C2B C3B 1.337(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.476(4) . ?
C3B H3B 0.9500 . ?
C4B C9B 1.387(4) . ?
C4B C5B 1.403(3) . ?
C5B C6B 1.377(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.388(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.392(3) . ?
C8B C9B 1.388(4) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.520(4) . ?
C11B C12B 1.550(4) . ?
C11B H11B 1.0000 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 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
O6A S1A O5A 120.54(13) . . ?
O6A S1A N1A 105.29(11) . . ?
O5A S1A N1A 107.63(11) . . ?
O6A S1A C7A 109.27(12) . . ?
O5A S1A C7A 106.59(12) . . ?
N1A S1A C7A 106.78(12) . . ?
C1A O1A H13A 119(5) . . ?
C10A O3A H14A 121(3) . . ?
C11A N1A S1A 120.38(16) . . ?
C11A N1A H15A 117(2) . . ?
S1A N1A H15A 111(2) . . ?
O2A C1A O1A 123.2(3) . . ?
O2A C1A C2A 121.3(3) . . ?
O1A C1A C2A 115.5(2) . . ?
C3A C2A C1A 122.1(2) . . ?
C3A C2A H2A 118.9 . . ?
C1A C2A H2A 118.9 . . ?
C2A C3A C4A 126.3(2) . . ?
C2A C3A H3A 116.9 . . ?
C4A C3A H3A 116.9 . . ?
C9A C4A C5A 119.3(3) . . ?
C9A C4A C3A 118.4(2) . . ?
C5A C4A C3A 122.3(2) . . ?
C6A C5A C4A 120.2(2) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C7A C6A C5A 119.5(2) . . ?
C7A C6A H6A 120.2 . . ?
C5A C6A H6A 120.2 . . ?
C6A C7A C8A 120.9(3) . . ?
C6A C7A S1A 121.1(2) . . ?
C8A C7A S1A 118.0(2) . . ?
C9A C8A C7A 119.8(3) . . ?
C9A C8A H8A 120.1 . . ?
C7A C8A H8A 120.1 . . ?
C8A C9A C4A 120.2(2) . . ?
C8A C9A H9A 119.9 . . ?
C4A C9A H9A 119.9 . . ?
O4A C10A O3A 124.8(2) . . ?
O4A C10A C11A 120.4(2) . . ?
O3A C10A C11A 114.7(2) . . ?
N1A C11A C10A 111.37(19) . . ?
N1A C11A C12A 109.7(2) . . ?
C10A C11A C12A 109.4(2) . . ?
N1A C11A H11A 108.8 . . ?
C10A C11A H11A 108.8 . . ?
C12A C11A H11A 108.8 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O5B S1B O6B 120.19(13) . . ?
O5B S1B N1B 105.22(11) . . ?
O6B S1B N1B 109.00(12) . . ?
O5B S1B C7B 109.16(12) . . ?
O6B S1B C7B 106.46(12) . . ?
N1B S1B C7B 106.02(13) . . ?
C1B O1B H13B 118(3) . . ?
C10B O3B H14B 117(4) . . ?
C11B N1B S1B 122.73(17) . . ?
C11B N1B H15B 122(2) . . ?
S1B N1B H15B 114(2) . . ?
O2B C1B O1B 123.1(3) . . ?
O2B C1B C2B 122.0(2) . . ?
O1B C1B C2B 114.9(2) . . ?
C3B C2B C1B 122.2(2) . . ?
C3B C2B H2B 118.9 . . ?
C1B C2B H2B 118.9 . . ?
C2B C3B C4B 126.1(2) . . ?
C2B C3B H3B 117.0 . . ?
C4B C3B H3B 117.0 . . ?
C9B C4B C5B 119.5(3) . . ?
C9B C4B C3B 118.8(2) . . ?
C5B C4B C3B 121.7(2) . . ?
C6B C5B C4B 120.7(2) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C5B C6B C7B 119.1(2) . . ?
C5B C6B H6B 120.5 . . ?
C7B C6B H6B 120.5 . . ?
C6B C7B C8B 121.2(3) . . ?
C6B C7B S1B 119.66(19) . . ?
C8B C7B S1B 119.0(2) . . ?
C9B C8B C7B 119.2(2) . . ?
C9B C8B H8B 120.4 . . ?
C7B C8B H8B 120.4 . . ?
C4B C9B C8B 120.3(2) . . ?
C4B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
O4B C10B O3B 123.8(3) . . ?
O4B C10B C11B 118.0(2) . . ?
O3B C10B C11B 118.2(2) . . ?
N1B C11B C10B 113.3(2) . . ?
N1B C11B C12B 109.1(2) . . ?
C10B C11B C12B 107.7(2) . . ?
N1B C11B H11B 108.9 . . ?
C10B C11B H11B 108.9 . . ?
C12B C11B H11B 108.9 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
O6A S1A N1A C11A 175.70(18) . . . . ?
O5A S1A N1A C11A -54.5(2) . . . . ?
C7A S1A N1A C11A 59.6(2) . . . . ?
O2A C1A C2A C3A 1.5(4) . . . . ?
O1A C1A C2A C3A -176.6(3) . . . . ?
C1A C2A C3A C4A 179.6(3) . . . . ?
C2A C3A C4A C9A 177.0(3) . . . . ?
C2A C3A C4A C5A -3.3(4) . . . . ?
C9A C4A C5A C6A 1.1(4) . . . . ?
C3A C4A C5A C6A -178.6(2) . . . . ?
C4A C5A C6A C7A -0.6(4) . . . . ?
C5A C6A C7A C8A -0.7(4) . . . . ?
C5A C6A C7A S1A 176.2(2) . . . . ?
O6A S1A C7A C6A 135.5(2) . . . . ?
O5A S1A C7A C6A 3.8(3) . . . . ?
N1A S1A C7A C6A -111.1(2) . . . . ?
O6A S1A C7A C8A -47.5(3) . . . . ?
O5A S1A C7A C8A -179.3(2) . . . . ?
N1A S1A C7A C8A 65.9(2) . . . . ?
C6A C7A C8A C9A 1.5(4) . . . . ?
S1A C7A C8A C9A -175.5(2) . . . . ?
C7A C8A C9A C4A -0.9(4) . . . . ?
C5A C4A C9A C8A -0.3(4) . . . . ?
C3A C4A C9A C8A 179.4(2) . . . . ?
S1A N1A C11A C10A -80.2(2) . . . . ?
S1A N1A C11A C12A 158.49(18) . . . . ?
O4A C10A C11A N1A -48.1(3) . . . . ?
O3A C10A C11A N1A 134.1(2) . . . . ?
O4A C10A C11A C12A 73.4(3) . . . . ?
O3A C10A C11A C12A -104.4(2) . . . . ?
O5B S1B N1B C11B -179.5(2) . . . . ?
O6B S1B N1B C11B -49.3(2) . . . . ?
C7B S1B N1B C11B 65.0(2) . . . . ?
O2B C1B C2B C3B -1.0(4) . . . . ?
O1B C1B C2B C3B 178.7(3) . . . . ?
C1B C2B C3B C4B -179.6(3) . . . . ?
C2B C3B C4B C9B 179.4(3) . . . . ?
C2B C3B C4B C5B -1.1(4) . . . . ?
C9B C4B C5B C6B -2.0(4) . . . . ?
C3B C4B C5B C6B 178.5(2) . . . . ?
C4B C5B C6B C7B 0.5(4) . . . . ?
C5B C6B C7B C8B 1.3(4) . . . . ?
C5B C6B C7B S1B -174.3(2) . . . . ?
O5B S1B C7B C6B -32.5(3) . . . . ?
O6B S1B C7B C6B -163.6(2) . . . . ?
N1B S1B C7B C6B 80.4(2) . . . . ?
O5B S1B C7B C8B 151.9(2) . . . . ?
O6B S1B C7B C8B 20.7(3) . . . . ?
N1B S1B C7B C8B -95.2(2) . . . . ?
C6B C7B C8B C9B -1.5(4) . . . . ?
S1B C7B C8B C9B 174.1(2) . . . . ?
C5B C4B C9B C8B 1.8(4) . . . . ?
C3B C4B C9B C8B -178.7(3) . . . . ?
C7B C8B C9B C4B -0.1(4) . . . . ?
S1B N1B C11B C10B -76.8(3) . . . . ?
S1B N1B C11B C12B 163.24(19) . . . . ?
O4B C10B C11B N1B 142.3(2) . . . . ?
O3B C10B C11B N1B -39.7(3) . . . . ?
O4B C10B C11B C12B -97.0(3) . . . . ?
O3B C10B C11B C12B 81.1(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
O1A H13A O4B 0.85(5) 1.81(5) 2.639(3) 164(8) .
O1B H13B O4A 0.85(3) 1.88(3) 2.725(3) 171(5) .
O3A H14A O2B 0.86(3) 1.75(3) 2.604(3) 172(5) .
O3B H14B O2A 0.85(3) 1.80(3) 2.647(3) 178(6) .
N1B H15B O1A 0.84(3) 2.18(3) 2.999(3) 167(3) 1_565
N1A H15A O4B 0.85(3) 2.16(3) 2.998(3) 168(3) 1_444

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.057

#==end

data_kaw101c
_database_code_depnum_ccdc_archive 'CCDC 787772'
#TrackingRef 'web_deposit_cif_file_0_KraigA.Wheeler_1281139506.cif'

# 3-IIa - photodimerized

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O12 S2'
_chemical_formula_sum            'C24 H26 N2 O12 S2'
_chemical_formula_weight         598.59
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.0750(3)
_cell_length_b                   8.3144(4)
_cell_length_c                   11.1366(5)
_cell_angle_alpha                94.937(3)
_cell_angle_beta                 102.315(3)
_cell_angle_gamma                102.312(3)
_cell_volume                     619.34(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3219
_cell_measurement_theta_min      4.100
_cell_measurement_theta_max      71.944

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12839
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         68.23
_reflns_number_total             3874
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_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^)+(0.0721P)^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    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   0.05(3)
_refine_ls_number_reflns         3874
_refine_ls_number_parameters     388
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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
S1A S 0.5415(2) 0.00739(17) 0.92488(14) 0.0433(4) Uani 1 1 d . . .
O1A O 1.2254(8) 0.8604(7) 1.4884(5) 0.0579(13) Uani 1 1 d D . .
O2A O 1.0105(6) 0.9774(6) 1.3681(4) 0.0524(12) Uani 1 1 d . . .
O3A O 1.0882(7) 0.2552(7) 0.9152(5) 0.0586(13) Uani 1 1 d D . .
O4A O 0.8660(8) 0.3236(6) 0.7657(5) 0.0608(13) Uani 1 1 d . . .
O5A O 0.6355(7) -0.1059(5) 0.9933(4) 0.0565(12) Uani 1 1 d . . .
O6A O 0.3318(6) -0.0218(5) 0.8913(5) 0.0614(13) Uani 1 1 d . . .
N1A N 0.6118(7) 0.0108(6) 0.7957(5) 0.0471(12) Uani 1 1 d D . .
H3 H 0.574(6) 0.074(5) 0.749(4) 0.044(11) Uiso 1 1 d D . .
H7 H 1.104(8) 1.194(4) 1.439(5) 0.049(17) Uiso 1 1 d D . .
H9 H 1.387(6) 1.608(8) 1.491(6) 0.05(2) Uiso 1 1 d D . .
H15 H 1.119(17) 0.361(3) 0.919(11) 0.14(5) Uiso 1 1 d D . .
H18 H 1.212(18) 0.947(9) 1.530(10) 0.16(6) Uiso 1 1 d D . .
H10 H 0.953(12) 0.569(6) 0.824(6) 0.08(3) Uiso 1 1 d D . .
C1A C 1.1049(10) 0.8733(8) 1.3827(6) 0.0417(16) Uani 1 1 d . . .
C2A C 1.1201(9) 0.7512(8) 1.2765(6) 0.0399(15) Uani 1 1 d . . .
H2A H 1.1561 0.6510 1.3049 0.048 Uiso 1 1 calc R . .
C3A C 0.9417(9) 0.7112(8) 1.1639(6) 0.0410(16) Uani 1 1 d . . .
H3A H 0.8484 0.7801 1.1746 0.049 Uiso 1 1 calc R . .
C4A C 0.8290(9) 0.5291(8) 1.1211(6) 0.0393(15) Uani 1 1 d . . .
C5A C 0.8888(9) 0.3954(8) 1.1692(7) 0.0417(15) Uani 1 1 d . . .
H5A H 0.9934 0.4145 1.2393 0.050 Uiso 1 1 calc R . .
C6A C 0.7966(9) 0.2343(8) 1.1155(6) 0.0422(16) Uani 1 1 d . . .
H6A H 0.8361 0.1448 1.1492 0.051 Uiso 1 1 calc R . .
C7A C 0.6445(9) 0.2096(8) 1.0107(6) 0.0370(14) Uani 1 1 d . . .
C8A C 0.5740(9) 0.3400(8) 0.9636(6) 0.0392(15) Uani 1 1 d . . .
H8A H 0.4666 0.3201 0.8950 0.047 Uiso 1 1 calc R . .
C9A C 0.6661(8) 0.5001(8) 1.0205(6) 0.0404(15) Uani 1 1 d . . .
H9A H 0.6188 0.5890 0.9912 0.048 Uiso 1 1 calc R . .
C10A C 0.9286(9) 0.2229(8) 0.8246(6) 0.0444(15) Uani 1 1 d . . .
C11A C 0.8249(9) 0.0381(7) 0.7968(6) 0.0442(14) Uani 1 1 d . . .
H11A H 0.8876 -0.0183 0.8624 0.053 Uiso 1 1 calc R . .
C12A C 0.8543(12) -0.0346(10) 0.6740(8) 0.066(2) Uani 1 1 d . . .
H12A H 0.7818 -0.1488 0.6539 0.099 Uiso 1 1 calc R . .
H12B H 0.9934 -0.0279 0.6808 0.099 Uiso 1 1 calc R . .
H12C H 0.8064 0.0269 0.6098 0.099 Uiso 1 1 calc R . .
S1B S 1.6391(2) 1.54416(18) 1.43627(15) 0.0471(4) Uani 1 1 d . . .
O1B O 0.9693(7) 0.6579(6) 0.8745(5) 0.0523(12) Uani 1 1 d D . .
O2B O 1.2098(7) 0.5735(6) 0.9998(5) 0.0535(12) Uani 1 1 d . . .
O3B O 1.1659(7) 1.2918(6) 1.4720(5) 0.0500(11) Uani 1 1 d D . .
O4B O 1.3349(7) 1.1779(5) 1.6204(4) 0.0534(12) Uani 1 1 d . . .
O5B O 1.6284(7) 1.6620(5) 1.3516(5) 0.0641(14) Uani 1 1 d . . .
O6B O 1.8238(7) 1.5472(6) 1.5203(5) 0.0656(14) Uani 1 1 d . . .
N1B N 1.4819(8) 1.5685(6) 1.5182(5) 0.0489(12) Uani 1 1 d D . .
C1B C 1.1005(10) 0.6690(9) 0.9812(6) 0.0449(17) Uani 1 1 d . . .
C2B C 1.0830(9) 0.7906(8) 1.0793(6) 0.0406(15) Uani 1 1 d . . .
H2B H 1.0461 0.8883 1.0469 0.049 Uiso 1 1 calc R . .
C3B C 1.2628(9) 0.8388(8) 1.1942(6) 0.0375(15) Uani 1 1 d . . .
H3B H 1.3602 0.7737 1.1846 0.045 Uiso 1 1 calc R . .
C4B C 1.3684(9) 1.0174(8) 1.2410(6) 0.0381(15) Uani 1 1 d . . .
C5B C 1.3066(9) 1.1493(8) 1.1907(6) 0.0411(16) Uani 1 1 d . . .
H5B H 1.2058 1.1295 1.1185 0.049 Uiso 1 1 calc R . .
C6B C 1.3951(9) 1.3124(8) 1.2481(6) 0.0420(16) Uani 1 1 d . . .
H6B H 1.3508 1.4005 1.2151 0.050 Uiso 1 1 calc R . .
C7B C 1.5483(9) 1.3426(8) 1.3537(6) 0.0386(15) Uani 1 1 d . . .
C8B C 1.6191(9) 1.2117(8) 1.3994(7) 0.0456(17) Uani 1 1 d . . .
H8B H 1.7264 1.2320 1.4681 0.055 Uiso 1 1 calc R . .
C9B C 1.5302(9) 1.0506(9) 1.3430(7) 0.0435(16) Uani 1 1 d . . .
H9B H 1.5793 0.9632 1.3737 0.052 Uiso 1 1 calc R . .
C10B C 1.3091(9) 1.2984(8) 1.5700(6) 0.0420(14) Uani 1 1 d . . .
C11B C 1.4405(9) 1.4721(7) 1.6155(5) 0.0450(14) Uani 1 1 d . . .
H11B H 1.5679 1.4612 1.6655 0.054 Uiso 1 1 calc R . .
C12B C 1.3435(13) 1.5642(10) 1.6994(7) 0.066(2) Uani 1 1 d . . .
H12D H 1.4289 1.6720 1.7325 0.100 Uiso 1 1 calc R . .
H12E H 1.3223 1.5024 1.7663 0.100 Uiso 1 1 calc R . .
H12F H 1.2180 1.5764 1.6525 0.100 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
S1A 0.0460(9) 0.0261(8) 0.0553(10) 0.0018(7) 0.0109(8) 0.0056(7)
O1A 0.077(3) 0.047(3) 0.037(3) -0.002(2) -0.004(2) 0.009(3)
O2A 0.043(3) 0.047(3) 0.059(3) -0.012(2) 0.002(2) 0.009(2)
O3A 0.049(3) 0.045(3) 0.069(3) -0.009(2) -0.010(2) 0.013(2)
O4A 0.068(3) 0.036(3) 0.066(3) 0.013(2) -0.007(2) 0.007(2)
O5A 0.075(3) 0.030(2) 0.066(3) 0.011(2) 0.015(3) 0.018(2)
O6A 0.047(3) 0.037(2) 0.091(4) -0.004(2) 0.013(2) 0.000(2)
N1A 0.048(3) 0.027(3) 0.058(3) 0.004(2) -0.005(3) 0.009(2)
C1A 0.042(3) 0.030(4) 0.044(4) -0.003(3) 0.006(3) -0.003(3)
C2A 0.045(3) 0.026(3) 0.043(4) -0.002(3) 0.002(3) 0.008(3)
C3A 0.036(3) 0.031(4) 0.054(4) 0.004(3) 0.009(3) 0.007(3)
C4A 0.040(3) 0.033(4) 0.043(4) 0.000(3) 0.006(3) 0.011(3)
C5A 0.042(3) 0.033(4) 0.046(4) -0.002(3) 0.003(3) 0.012(3)
C6A 0.048(4) 0.035(4) 0.044(4) 0.010(3) 0.008(3) 0.010(3)
C7A 0.037(3) 0.026(3) 0.046(4) -0.004(3) 0.014(3) 0.003(3)
C8A 0.036(3) 0.035(4) 0.042(4) 0.004(3) 0.000(3) 0.008(3)
C9A 0.031(3) 0.028(3) 0.056(4) 0.000(3) -0.001(3) 0.007(3)
C10A 0.038(3) 0.043(4) 0.046(4) -0.004(3) 0.007(3) 0.004(3)
C11A 0.049(3) 0.028(3) 0.051(4) 0.007(2) 0.003(3) 0.008(3)
C12A 0.077(6) 0.051(5) 0.066(5) -0.005(4) 0.024(4) 0.007(4)
S1B 0.0489(9) 0.0270(8) 0.0596(11) 0.0000(7) 0.0112(8) 0.0005(7)
O1B 0.054(3) 0.051(3) 0.043(3) 0.003(2) 0.004(2) 0.002(2)
O2B 0.043(2) 0.044(3) 0.067(3) -0.011(2) 0.010(2) 0.007(2)
O3B 0.047(3) 0.037(3) 0.056(3) -0.003(2) -0.004(2) 0.007(2)
O4B 0.068(3) 0.036(2) 0.049(3) 0.008(2) 0.004(2) 0.007(2)
O5B 0.084(4) 0.030(2) 0.078(3) 0.007(2) 0.028(3) 0.003(2)
O6B 0.046(2) 0.045(3) 0.088(4) -0.012(2) -0.004(2) 0.000(2)
N1B 0.057(3) 0.031(3) 0.055(3) 0.006(2) 0.002(3) 0.012(3)
C1B 0.041(4) 0.042(4) 0.047(4) 0.005(3) 0.013(3) -0.004(3)
C2B 0.045(3) 0.030(3) 0.041(4) 0.004(3) 0.000(3) 0.008(3)
C3B 0.036(3) 0.034(4) 0.035(3) -0.008(3) -0.003(3) 0.008(3)
C4B 0.041(3) 0.028(4) 0.046(4) 0.003(3) 0.014(3) 0.006(3)
C5B 0.041(4) 0.039(4) 0.038(4) 0.006(3) -0.001(3) 0.007(3)
C6B 0.043(3) 0.032(4) 0.051(4) 0.004(3) 0.009(3) 0.011(3)
C7B 0.040(3) 0.026(3) 0.049(4) 0.008(3) 0.010(3) 0.006(3)
C8B 0.036(3) 0.031(4) 0.061(5) 0.002(3) -0.001(3) 0.003(3)
C9B 0.045(4) 0.031(4) 0.054(4) 0.006(3) 0.007(3) 0.010(3)
C10B 0.045(3) 0.042(4) 0.037(3) -0.004(3) 0.006(3) 0.015(3)
C11B 0.047(3) 0.042(3) 0.041(3) 0.004(3) 0.004(3) 0.007(3)
C12B 0.097(6) 0.047(5) 0.053(4) -0.004(4) 0.019(4) 0.013(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
S1A O6A 1.412(4) . ?
S1A O5A 1.444(4) . ?
S1A N1A 1.620(6) . ?
S1A C7A 1.782(7) . ?
O1A C1A 1.326(8) . ?
O1A H18 0.86(9) . ?
O2A C1A 1.203(8) . ?
O3A C10A 1.305(7) . ?
O3A H15 0.86(2) . ?
O4A C10A 1.207(7) . ?
N1A C11A 1.473(7) . ?
N1A H3 0.82(4) . ?
C1A C2A 1.528(10) . ?
C2A C3A 1.533(8) . ?
C2A C3B 1.607(9) . ?
C2A H2A 0.9800 . ?
C3A C4A 1.534(9) . ?
C3A C2B 1.596(9) . ?
C3A H3A 0.9800 . ?
C4A C5A 1.381(9) . ?
C4A C9A 1.388(8) . ?
C5A C6A 1.379(9) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.375(9) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.384(8) . ?
C8A C9A 1.382(9) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.528(8) . ?
C11A C12A 1.520(10) . ?
C11A H11A 0.9800 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
S1B O5B 1.420(5) . ?
S1B O6B 1.430(5) . ?
S1B N1B 1.615(6) . ?
S1B C7B 1.758(7) . ?
O1B C1B 1.325(8) . ?
O1B H10 0.86(6) . ?
O2B C1B 1.222(8) . ?
O3B C10B 1.310(7) . ?
O3B H7 0.85(2) . ?
O4B C10B 1.218(7) . ?
N1B C11B 1.445(7) . ?
N1B H9 0.82(5) . ?
C1B C2B 1.467(10) . ?
C2B C3B 1.554(8) . ?
C2B H2B 0.9800 . ?
C3B C4B 1.504(8) . ?
C3B H3B 0.9800 . ?
C4B C5B 1.384(9) . ?
C4B C9B 1.390(9) . ?
C5B C6B 1.399(10) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.382(9) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.384(8) . ?
C8B C9B 1.383(10) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.519(8) . ?
C11B C12B 1.518(10) . ?
C11B H11B 0.9800 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?

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
O6A S1A O5A 120.2(3) . . ?
O6A S1A N1A 105.6(3) . . ?
O5A S1A N1A 107.2(3) . . ?
O6A S1A C7A 109.6(3) . . ?
O5A S1A C7A 106.9(3) . . ?
N1A S1A C7A 106.5(3) . . ?
C1A O1A H18 96(9) . . ?
C10A O3A H15 99(8) . . ?
C11A N1A S1A 120.1(4) . . ?
C11A N1A H3 103(3) . . ?
S1A N1A H3 118(3) . . ?
O2A C1A O1A 125.2(7) . . ?
O2A C1A C2A 123.5(6) . . ?
O1A C1A C2A 111.0(6) . . ?
C1A C2A C3A 114.9(5) . . ?
C1A C2A C3B 112.1(5) . . ?
C3A C2A C3B 90.6(5) . . ?
C1A C2A H2A 112.5 . . ?
C3A C2A H2A 112.5 . . ?
C3B C2A H2A 112.5 . . ?
C2A C3A C4A 118.5(5) . . ?
C2A C3A C2B 90.1(4) . . ?
C4A C3A C2B 115.8(5) . . ?
C2A C3A H3A 110.3 . . ?
C4A C3A H3A 110.3 . . ?
C2B C3A H3A 110.3 . . ?
C5A C4A C9A 119.2(7) . . ?
C5A C4A C3A 124.4(6) . . ?
C9A C4A C3A 116.2(5) . . ?
C6A C5A C4A 121.4(7) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C7A C6A C5A 118.2(6) . . ?
C7A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
C6A C7A C8A 122.0(7) . . ?
C6A C7A S1A 120.4(5) . . ?
C8A C7A S1A 117.5(5) . . ?
C9A C8A C7A 118.7(6) . . ?
C9A C8A H8A 120.6 . . ?
C7A C8A H8A 120.6 . . ?
C8A C9A C4A 120.3(6) . . ?
C8A C9A H9A 119.8 . . ?
C4A C9A H9A 119.8 . . ?
O4A C10A O3A 125.6(7) . . ?
O4A C10A C11A 121.7(6) . . ?
O3A C10A C11A 112.7(6) . . ?
N1A C11A C12A 111.2(5) . . ?
N1A C11A C10A 111.4(5) . . ?
C12A C11A C10A 109.5(6) . . ?
N1A C11A H11A 108.2 . . ?
C12A C11A H11A 108.2 . . ?
C10A C11A H11A 108.2 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O5B S1B O6B 120.4(3) . . ?
O5B S1B N1B 105.5(3) . . ?
O6B S1B N1B 107.5(3) . . ?
O5B S1B C7B 109.2(3) . . ?
O6B S1B C7B 107.4(3) . . ?
N1B S1B C7B 105.9(3) . . ?
C1B O1B H10 115(6) . . ?
C10B O3B H7 114(4) . . ?
C11B N1B S1B 124.9(4) . . ?
C11B N1B H9 110(5) . . ?
S1B N1B H9 121(5) . . ?
O2B C1B O1B 122.7(7) . . ?
O2B C1B C2B 123.1(7) . . ?
O1B C1B C2B 113.7(6) . . ?
C1B C2B C3B 115.2(5) . . ?
C1B C2B C3A 113.2(5) . . ?
C3B C2B C3A 90.2(5) . . ?
C1B C2B H2B 112.2 . . ?
C3B C2B H2B 112.2 . . ?
C3A C2B H2B 112.2 . . ?
C4B C3B C2B 121.4(5) . . ?
C4B C3B C2A 115.5(5) . . ?
C2B C3B C2A 89.0(4) . . ?
C4B C3B H3B 109.7 . . ?
C2B C3B H3B 109.7 . . ?
C2A C3B H3B 109.7 . . ?
C5B C4B C9B 118.8(7) . . ?
C5B C4B C3B 123.0(6) . . ?
C9B C4B C3B 118.1(5) . . ?
C4B C5B C6B 120.3(6) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C7B C6B C5B 120.0(6) . . ?
C7B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C6B C7B C8B 119.8(7) . . ?
C6B C7B S1B 120.0(5) . . ?
C8B C7B S1B 120.1(5) . . ?
C9B C8B C7B 119.9(6) . . ?
C9B C8B H8B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C9B C4B 120.9(6) . . ?
C8B C9B H9B 119.5 . . ?
C4B C9B H9B 119.5 . . ?
O4B C10B O3B 123.7(6) . . ?
O4B C10B C11B 123.0(6) . . ?
O3B C10B C11B 113.3(6) . . ?
N1B C11B C12B 109.7(6) . . ?
N1B C11B C10B 114.6(5) . . ?
C12B C11B C10B 108.7(5) . . ?
N1B C11B H11B 107.8 . . ?
C12B C11B H11B 107.8 . . ?
C10B C11B H11B 107.8 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
O6A S1A N1A C11A -179.7(4) . . . . ?
O5A S1A N1A C11A -50.3(5) . . . . ?
C7A S1A N1A C11A 63.9(5) . . . . ?
O2A C1A C2A C3A -27.3(9) . . . . ?
O1A C1A C2A C3A 159.5(6) . . . . ?
O2A C1A C2A C3B 74.2(8) . . . . ?
O1A C1A C2A C3B -99.0(6) . . . . ?
C1A C2A C3A C4A -123.1(6) . . . . ?
C3B C2A C3A C4A 122.2(5) . . . . ?
C1A C2A C3A C2B 117.1(5) . . . . ?
C3B C2A C3A C2B 2.3(6) . . . . ?
C2A C3A C4A C5A -6.9(9) . . . . ?
C2B C3A C4A C5A 98.6(8) . . . . ?
C2A C3A C4A C9A 178.6(6) . . . . ?
C2B C3A C4A C9A -75.9(7) . . . . ?
C9A C4A C5A C6A 3.4(10) . . . . ?
C3A C4A C5A C6A -171.0(6) . . . . ?
C4A C5A C6A C7A 1.1(10) . . . . ?
C5A C6A C7A C8A -4.5(10) . . . . ?
C5A C6A C7A S1A 171.6(5) . . . . ?
O6A S1A C7A C6A 136.6(5) . . . . ?
O5A S1A C7A C6A 4.8(6) . . . . ?
N1A S1A C7A C6A -109.6(5) . . . . ?
O6A S1A C7A C8A -47.2(6) . . . . ?
O5A S1A C7A C8A -179.0(5) . . . . ?
N1A S1A C7A C8A 66.6(5) . . . . ?
C6A C7A C8A C9A 3.2(10) . . . . ?
S1A C7A C8A C9A -172.9(5) . . . . ?
C7A C8A C9A C4A 1.4(9) . . . . ?
C5A C4A C9A C8A -4.6(10) . . . . ?
C3A C4A C9A C8A 170.2(6) . . . . ?
S1A N1A C11A C12A 155.4(5) . . . . ?
S1A N1A C11A C10A -82.1(6) . . . . ?
O4A C10A C11A N1A -52.9(8) . . . . ?
O3A C10A C11A N1A 128.0(6) . . . . ?
O4A C10A C11A C12A 70.6(8) . . . . ?
O3A C10A C11A C12A -108.5(7) . . . . ?
O5B S1B N1B C11B 179.0(5) . . . . ?
O6B S1B N1B C11B -51.3(6) . . . . ?
C7B S1B N1B C11B 63.3(6) . . . . ?
O2B C1B C2B C3B 22.2(9) . . . . ?
O1B C1B C2B C3B -165.8(5) . . . . ?
O2B C1B C2B C3A -79.7(8) . . . . ?
O1B C1B C2B C3A 92.3(7) . . . . ?
C2A C3A C2B C1B 115.3(5) . . . . ?
C4A C3A C2B C1B -6.9(8) . . . . ?
C2A C3A C2B C3B -2.4(6) . . . . ?
C4A C3A C2B C3B -124.6(5) . . . . ?
C1B C2B C3B C4B 126.8(6) . . . . ?
C3A C2B C3B C4B -117.3(6) . . . . ?
C1B C2B C3B C2A -113.6(5) . . . . ?
C3A C2B C3B C2A 2.3(6) . . . . ?
C1A C2A C3B C4B 5.0(7) . . . . ?
C3A C2A C3B C4B 122.3(5) . . . . ?
C1A C2A C3B C2B -119.7(5) . . . . ?
C3A C2A C3B C2B -2.4(6) . . . . ?
C2B C3B C4B C5B 4.1(10) . . . . ?
C2A C3B C4B C5B -101.5(7) . . . . ?
C2B C3B C4B C9B -178.9(6) . . . . ?
C2A C3B C4B C9B 75.5(7) . . . . ?
C9B C4B C5B C6B -5.2(10) . . . . ?
C3B C4B C5B C6B 171.8(6) . . . . ?
C4B C5B C6B C7B 1.6(11) . . . . ?
C5B C6B C7B C8B 2.7(10) . . . . ?
C5B C6B C7B S1B -172.3(5) . . . . ?
O5B S1B C7B C6B -33.9(7) . . . . ?
O6B S1B C7B C6B -166.1(6) . . . . ?
N1B S1B C7B C6B 79.3(6) . . . . ?
O5B S1B C7B C8B 151.1(5) . . . . ?
O6B S1B C7B C8B 19.0(6) . . . . ?
N1B S1B C7B C8B -95.7(6) . . . . ?
C6B C7B C8B C9B -3.1(10) . . . . ?
S1B C7B C8B C9B 171.8(5) . . . . ?
C7B C8B C9B C4B -0.6(10) . . . . ?
C5B C4B C9B C8B 4.8(10) . . . . ?
C3B C4B C9B C8B -172.4(6) . . . . ?
S1B N1B C11B C12B 160.7(5) . . . . ?
S1B N1B C11B C10B -76.6(6) . . . . ?
O4B C10B C11B N1B 141.7(6) . . . . ?
O3B C10B C11B N1B -38.6(8) . . . . ?
O4B C10B C11B C12B -95.1(7) . . . . ?
O3B C10B C11B C12B 84.6(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
O1A H18 O4B 0.86(9) 2.01(7) 2.776(7) 149(11) .
O3B H7 O2A 0.85(2) 1.82(2) 2.663(7) 170(6) .
O3A H15 O2B 0.86(2) 1.83(6) 2.624(7) 154(12) .
O1B H10 O4A 0.86(6) 2.01(4) 2.811(8) 155(8) .
N1B H9 O1A 0.82(5) 2.60(4) 3.325(8) 149(6) 1_565
N1A H3 O4B 0.82(4) 2.34(3) 3.095(6) 155(4) 1_444
C9B H9B O5B 0.93 2.60 3.451(8) 152.6 1_545
C9A H9A O5A 0.93 2.51 3.364(7) 152.4 1_565

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.063

#==end