 
data_kaw117_twin5 

# rac-3 unreacted
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety           
 'C15 H19 N O6 S' 
_chemical_formula_sum 
 'C15 H19 N O6 S' 
_chemical_formula_weight          341.37 
 
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' 
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    7.0006(3) 
_cell_length_b                    7.8988(4) 
_cell_length_c                    14.9207(7) 
_cell_angle_alpha                 92.055(3) 
_cell_angle_beta                  102.842(3) 
_cell_angle_gamma                 97.201(3) 
_cell_volume                      796.34(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     2984
_cell_measurement_theta_min       3.045
_cell_measurement_theta_max       67.007
 
_exptl_crystal_description        'transparent plate'
_exptl_crystal_colour             'colorless'
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.191
_exptl_crystal_size_mid           0.164
_exptl_crystal_size_min           0.029
_exptl_crystal_density_diffrn     1.424 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              360 
_exptl_absorpt_coefficient_mu     2.092 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.691 
_exptl_absorpt_correction_T_max   0.942 
_exptl_absorpt_process_details    
  'SADABS (Bruker, 2010)'
 
_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_reflns_number             7101
_diffrn_reflns_av_unetI/netI      0.0927
_diffrn_reflns_av_R_equivalents   0.0494
_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        0
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.044
_diffrn_reflns_theta_max          67.983
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.968
_diffrn_measured_fraction_theta_full  0.972
_diffrn_reflns_Laue_measured_fraction_max    0.968
_diffrn_reflns_Laue_measured_fraction_full   0.972
_diffrn_reflns_point_group_measured_fraction_max   0.968
_diffrn_reflns_point_group_measured_fraction_full  0.972
_reflns_number_total              5223
_reflns_number_gt                 3562
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_computing_data_collection     'APEX2 (Bruker, 2010)'
_computing_cell_refinement     'APEX2'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material     'XSEED (Barbour, 2001)' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

Inspection of the crystal sample with optical microscopy revealed possible 
 fractures and occlusions.  The reflection data exhibited crystal twinning
 most likely due to these fractures.  A unit cell was determined using
 Cell_Now on 439 reflections.  The data were corrected for absorption
 with Twinabs using a two component model with a ratio of 1857:1127
 refls (2984 total).  The structure was solved using hklf4 and refined
 using both twin components (hklf5).

This structure represents the third of three datasets collected for
 this compound. Each time a fresh crystal was chosen with each
 exhibiting noticeable crystal deffects - the lack of sharp crystal
 extinction via a polarizing microscope.  This sample and structures
 represents the best refinement model.

All non-hydrogen atoms were located in a difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with O/N-H bond distances
 of 0.85(2) angstroms.

;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5223
_refine_ls_number_parameters      221
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1089
_refine_ls_R_factor_gt            0.0638
_refine_ls_wR_factor_ref          0.1713
_refine_ls_wR_factor_gt           0.1459
_refine_ls_goodness_of_fit_ref    0.965
_refine_ls_restrained_S_all       0.965
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.02168(17) 0.71477(15) 0.25790(8) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.3687(5) 1.6608(4) 0.6126(2) 0.0298(8) Uani 1 1 d D . . . .
H20 H 0.412(7) 1.756(4) 0.639(3) 0.036 Uiso 1 1 d D U . . .
O2 O 0.5344(5) 1.5338(4) 0.7316(2) 0.0298(8) Uani 1 1 d . . . . .
O3 O 0.2930(5) 1.1778(4) 0.1762(2) 0.0308(8) Uani 1 1 d D . . . .
H21 H 0.353(7) 1.271(4) 0.205(3) 0.037 Uiso 1 1 d D U . . .
O4 O 0.4766(5) 1.0411(4) 0.2862(2) 0.0273(7) Uani 1 1 d . . . . .
O5 O -0.1524(5) 0.7354(4) 0.1902(2) 0.0357(8) Uani 1 1 d . . . . .
O6 O 0.0327(5) 0.5615(4) 0.3057(2) 0.0380(9) Uani 1 1 d . . . . .
N1 N 0.2070(6) 0.7340(5) 0.2092(3) 0.0256(9) Uani 1 1 d D . . . .
H22 H 0.288(6) 0.667(5) 0.226(3) 0.031 Uiso 1 1 d D U . . .
C1 C 0.4277(6) 1.5253(6) 0.6537(3) 0.0255(10) Uani 1 1 d . . . . .
C2 C 0.3591(7) 1.3616(6) 0.6000(3) 0.0275(10) Uani 1 1 d . . . . .
H2 H 0.3970 1.2611 0.6280 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2480(7) 1.3441(6) 0.5151(3) 0.0265(10) Uani 1 1 d . . . . .
H3 H 0.2063 1.4452 0.4891 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1828(6) 1.1843(6) 0.4573(3) 0.0254(10) Uani 1 1 d . . . . .
C5 C 0.0521(7) 1.1870(6) 0.3718(3) 0.0272(11) Uani 1 1 d . . . . .
H5 H 0.0033 1.2905 0.3538 0.033 Uiso 1 1 calc R U . . .
C6 C -0.0074(7) 1.0409(6) 0.3130(3) 0.0276(10) Uani 1 1 d . . . . .
H6 H -0.0980 1.0430 0.2554 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0676(7) 0.8919(5) 0.3397(3) 0.0245(10) Uani 1 1 d . . . . .
C8 C 0.1934(7) 0.8841(6) 0.4251(3) 0.0253(10) Uani 1 1 d . . . . .
H8 H 0.2405 0.7798 0.4428 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2494(7) 1.0286(6) 0.4839(3) 0.0255(10) Uani 1 1 d . . . . .
H9 H 0.3337 1.0234 0.5429 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3506(7) 1.0415(6) 0.2147(3) 0.0256(10) Uani 1 1 d . . . . .
C11 C 0.2442(7) 0.8795(5) 0.1561(3) 0.0249(10) Uani 1 1 d . . . . .
H11 H 0.1137 0.9057 0.1205 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3666(7) 0.8395(6) 0.0872(3) 0.0299(11) Uani 1 1 d . . . . .
H12A H 0.4961 0.8130 0.1218 0.036 Uiso 1 1 calc R U . . .
H12B H 0.3919 0.9434 0.0541 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2728(7) 0.6916(6) 0.0162(3) 0.0283(11) Uani 1 1 d . . . . .
H13 H 0.2670 0.5837 0.0492 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0650(8) 0.7116(7) -0.0338(3) 0.0417(13) Uani 1 1 d . . . . .
H14A H -0.0213 0.7055 0.0098 0.063 Uiso 1 1 calc R U . . .
H14B H 0.0161 0.6198 -0.0825 0.063 Uiso 1 1 calc R U . . .
H14C H 0.0654 0.8225 -0.0612 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4031(9) 0.6759(7) -0.0522(4) 0.0441(14) Uani 1 1 d . . . . .
H15A H 0.3964 0.7735 -0.0911 0.066 Uiso 1 1 calc R U . . .
H15B H 0.3565 0.5695 -0.0910 0.066 Uiso 1 1 calc R U . . .
H15C H 0.5401 0.6748 -0.0186 0.066 Uiso 1 1 calc R U . . .
 
 
_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 O6 1.429(3) . ?
S1 O5 1.431(3) . ?
S1 N1 1.616(4) . ?
S1 C7 1.772(4) . ?
O1 C1 1.319(5) . ?
O1 H20 0.82(3) . ?
O2 C1 1.228(5) . ?
O3 C10 1.305(5) . ?
O3 H21 0.84(3) . ?
O4 C10 1.225(5) . ?
N1 C11 1.448(5) . ?
N1 H22 0.83(2) . ?
C1 C2 1.464(6) . ?
C2 C3 1.323(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.466(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(6) . ?
C4 C9 1.409(6) . ?
C5 C6 1.386(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(6) . ?
C8 C9 1.374(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.533(6) . ?
C11 C12 1.524(6) . ?
C11 H11 1.0000 . ?
C12 C13 1.526(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.510(6) . ?
C13 C15 1.524(7) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O6 S1 O5 120.5(2) . . ?
O6 S1 N1 106.0(2) . . ?
O5 S1 N1 108.2(2) . . ?
O6 S1 C7 108.8(2) . . ?
O5 S1 C7 107.0(2) . . ?
N1 S1 C7 105.4(2) . . ?
C1 O1 H20 118(4) . . ?
C10 O3 H21 114(4) . . ?
C11 N1 S1 120.9(3) . . ?
C11 N1 H22 124(4) . . ?
S1 N1 H22 114(3) . . ?
O2 C1 O1 123.0(4) . . ?
O2 C1 C2 121.5(4) . . ?
O1 C1 C2 115.5(4) . . ?
C3 C2 C1 124.4(4) . . ?
C3 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
C2 C3 C4 126.4(4) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C5 C4 C9 118.7(4) . . ?
C5 C4 C3 118.8(4) . . ?
C9 C4 C3 122.5(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 118.8(4) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 121.5(4) . . ?
C6 C7 S1 118.7(4) . . ?
C8 C7 S1 119.5(3) . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 120.5(4) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
O4 C10 O3 125.3(4) . . ?
O4 C10 C11 124.0(4) . . ?
O3 C10 C11 110.6(4) . . ?
N1 C11 C12 111.4(4) . . ?
N1 C11 C10 114.0(4) . . ?
C12 C11 C10 107.7(4) . . ?
N1 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C10 C11 H11 107.8 . . ?
C11 C12 C13 115.2(4) . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C15 110.4(4) . . ?
C14 C13 C12 112.6(4) . . ?
C15 C13 C12 109.3(4) . . ?
C14 C13 H13 108.2 . . ?
C15 C13 H13 108.2 . . ?
C12 C13 H13 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O6 S1 N1 C11 -178.5(3) . . . . ?
O5 S1 N1 C11 51.0(4) . . . . ?
C7 S1 N1 C11 -63.2(4) . . . . ?
O2 C1 C2 C3 -178.3(5) . . . . ?
O1 C1 C2 C3 1.1(7) . . . . ?
C1 C2 C3 C4 177.2(4) . . . . ?
C2 C3 C4 C5 174.8(5) . . . . ?
C2 C3 C4 C9 -6.3(7) . . . . ?
C9 C4 C5 C6 -1.7(7) . . . . ?
C3 C4 C5 C6 177.3(4) . . . . ?
C4 C5 C6 C7 -1.0(7) . . . . ?
C5 C6 C7 C8 2.8(7) . . . . ?
C5 C6 C7 S1 -170.5(3) . . . . ?
O6 S1 C7 C6 -155.3(3) . . . . ?
O5 S1 C7 C6 -23.6(4) . . . . ?
N1 S1 C7 C6 91.4(4) . . . . ?
O6 S1 C7 C8 31.3(4) . . . . ?
O5 S1 C7 C8 162.9(4) . . . . ?
N1 S1 C7 C8 -82.1(4) . . . . ?
C6 C7 C8 C9 -1.7(7) . . . . ?
S1 C7 C8 C9 171.6(3) . . . . ?
C7 C8 C9 C4 -1.1(7) . . . . ?
C5 C4 C9 C8 2.8(7) . . . . ?
C3 C4 C9 C8 -176.2(4) . . . . ?
S1 N1 C11 C12 -157.2(3) . . . . ?
S1 N1 C11 C10 80.6(4) . . . . ?
O4 C10 C11 N1 35.1(6) . . . . ?
O3 C10 C11 N1 -147.0(4) . . . . ?
O4 C10 C11 C12 -89.1(5) . . . . ?
O3 C10 C11 C12 88.8(4) . . . . ?
N1 C11 C12 C13 60.1(5) . . . . ?
C10 C11 C12 C13 -174.2(4) . . . . ?
C11 C12 C13 C14 52.5(6) . . . . ?
C11 C12 C13 C15 175.5(4) . . . . ?
 
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 H20 O4  0.82(3) 1.90(3) 2.716(4) 173(5) 2_686
O3 H21 O2  0.84(3) 1.78(3) 2.624(4) 176(5) 2_686
N1 H22 O2  0.83(2) 2.16(3) 2.986(5) 172(5) 2_676
 
_refine_diff_density_max    0.304
_refine_diff_density_min   -0.348
_refine_diff_density_rms    0.070

_shelxl_version_number 2013-4



#==END

 
data_kaw114a
# rac-3 UV irradiated

# start Validation Reply Form
_vrf_RFACR01_kaw114a
;
PROBLEM: The value of the weighted R factor is > 0.45
RESPONSE: Ill-effects of crystal degradation due
to UV exposue. Noticeable crystal fractures.
;
_vrf_RFACG01_kaw114a
;
PROBLEM: The value of the R factor is > 0.15
RESPONSE: Ill-effects of crystal degradation due
to UV exposue.
;
_vrf_PLAT029_kaw114a
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.929       
RESPONSE: crystal diffraction power reduced due to the 
ill-effects of crystal degradation from UV exposue.
;
_vrf_PLAT084_kaw114a
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.49       
RESPONSE: Ill-effects of crystal degradation due
to UV exposue.
;
_vrf_PLAT413_kaw114a
;
PROBLEM: Short Inter XH3 .. XHn     H14B   ..  H14B    ..       1.84 Ang.  
RESPONSE: The result of crystal disorder from
photodimerization.
;
_vrf_PLAT082_kaw114a
;
PROBLEM: High R1 Value ..................................       0.19       
RESPONSE: Ill-effects of crystal degradation due
to UV exposue.
;
_vrf_PLAT340_kaw114a
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0240 Ang.  
RESPONSE: Ill-effects of crystal degradation due
to UV exposue.
;
# end Validation Reply Form

 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C15 H19 N O6 S' 
_chemical_formula_sum
 'C15 H19 N O6 S' 
_chemical_formula_weight          341.37

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.0252(15)
_cell_length_b                    8.1514(16)
_cell_length_c                    14.875(3)
_cell_angle_alpha                 97.853(11)
_cell_angle_beta                  103.477(8)
_cell_angle_gamma                 100.941(8)
_cell_volume                      798.6(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2665
_cell_measurement_theta_min       3.111
_cell_measurement_theta_max       64.076
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.420          
_exptl_crystal_F_000              360
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.19 
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.03
_exptl_absorpt_coefficient_mu     2.086
_shelx_estimated_absorpt_T_min    0.673 
_shelx_estimated_absorpt_T_max    0.939 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.673
_exptl_absorpt_correction_T_max   0.939
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             14209
_diffrn_reflns_av_unetI/netI      0.0846
_diffrn_reflns_av_R_equivalents   0.1137
_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        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.111
_diffrn_reflns_theta_max          67.971
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.925
_diffrn_measured_fraction_theta_full  0.929
_diffrn_reflns_Laue_measured_fraction_max    0.925
_diffrn_reflns_Laue_measured_fraction_full   0.929
_diffrn_reflns_point_group_measured_fraction_max   0.925
_diffrn_reflns_point_group_measured_fraction_full  0.929
_reflns_number_total              2700
_reflns_number_gt                 1689
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a series of difference density.
 maps and refined with anisotropic displacement parameters.  All CH
 hydrogen atoms were placed in calculated positions with 
 Ueq = 1.2 x Uiso to the corresponding C atom (1.5 x Uiso for methyl H
 atoms).  Each OH and NH hydrogen atom was located in a difference density
 map and refined using Ueq = 1.2 x Uiso and then placed in idealized
 positions and restrained with O/N-H bond distances of 0.85(2) angstroms.

Each phenyl ring was restrain with the FLAT and RIGU commands.

This sample represent the outcome of a UV illumination study of rac-3.  This
 was conducted by irradiation the crystal with a 200W Xe(Hg) lamp 
 equipped with a 360nm cur-on filter for 18hrs.  Refinement of the occupancy
 factors for the reactant and product phases resulted in 40:60 ratio of 
 components, respectively.  The poor R values and structural model is the 
 direct result of crystal decomposition from UV exposure.  This decomposition
 can be seen in highly diffuse and a sharp decrease in the intensity of 
 diffraction peaks.
;
 
_computing_data_collection     'APEX2 (Bruker, 2010)'
_computing_cell_refinement     'APEX2'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material     'XSEED (Barbour, 2001)' 
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1688P)²+7.9708P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2700
_refine_ls_number_parameters      274
_refine_ls_number_restraints      75
_refine_ls_R_factor_all           0.2373
_refine_ls_R_factor_gt            0.1915
_refine_ls_wR_factor_ref          0.4949
_refine_ls_wR_factor_gt           0.4683
_refine_ls_goodness_of_fit_ref    1.093
_refine_ls_restrained_S_all       1.079
_refine_ls_shift/su_max           0.011
_refine_ls_shift/su_mean          0.002
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.4725(7) 0.1946(5) 0.7794(4) 0.1062(18) Uani 1 1 d . . . . .
O1 O 1.1071(16) 1.1020(11) 1.2332(7) 0.089(3) Uani 1 1 d D . . . .
H20 H 1.1263 1.1955 1.2666 0.107 Uiso 1 1 calc DR U . . .
O2 O 0.8974(14) 1.2073(12) 1.1323(7) 0.084(3) Uani 1 1 d . . . . .
O3 O 0.9530(15) 0.4706(12) 0.7722(7) 0.090(3) Uani 1 1 d D . . . .
H21 H 1.0242 0.5672 0.7848 0.109 Uiso 1 1 calc DR U . . .
O4 O 0.7517(17) 0.5808(12) 0.6678(7) 0.096(3) Uani 1 1 d . . . . .
O5 O 0.480(2) 0.0689(17) 0.8371(12) 0.154(6) Uani 1 1 d . . . . .
O6 O 0.2874(19) 0.1952(16) 0.7135(11) 0.152(6) Uani 1 1 d . . . . .
N1 N 0.635(2) 0.1747(15) 0.7217(9) 0.095(4) Uani 1 1 d D . . . .
H22 H 0.7006 0.0973 0.7319 0.114 Uiso 1 1 calc DR U . . .
C1 C 0.990(2) 1.0969(15) 1.1564(10) 0.074(4) Uani 1 1 d . . . . .
C2 C 0.896(4) 0.897(4) 1.099(2) 0.063(10) Uani 0.40(3) 1 d . . P A 1
H2 H 0.9526 0.8118 1.1212 0.076 Uiso 0.40(3) 1 calc R U P A 1
C3 C 0.743(7) 0.856(5) 1.023(2) 0.075(12) Uani 0.40(3) 1 d . . P A 1
H3 H 0.6748 0.9379 1.0039 0.091 Uiso 0.40(3) 1 calc R U P A 1
C4 C 0.682(5) 0.687(4) 0.969(2) 0.063(8) Uani 0.40(3) 1 d D U P A 1
C5 C 0.548(5) 0.676(5) 0.881(2) 0.063(10) Uani 0.40(3) 1 d D U P A 1
H5 H 0.5045 0.7715 0.8648 0.076 Uiso 0.40(3) 1 calc R U P A 1
C6 C 0.480(5) 0.523(5) 0.819(2) 0.063(10) Uani 0.40(3) 1 d D U P A 1
H6 H 0.3920 0.5095 0.7596 0.075 Uiso 0.40(3) 1 calc R U P A 1
C7 C 0.5508(19) 0.3950(17) 0.8518(9) 0.068(3) Uani 1 1 d . U . . .
C8 C 0.671(8) 0.390(6) 0.927(4) 0.12(3) Uani 0.40(3) 1 d D U P A 1
H8 H 0.7111 0.2907 0.9393 0.146 Uiso 0.40(3) 1 calc R U P A 1
C9 C 0.738(6) 0.537(6) 0.989(3) 0.089(13) Uani 0.40(3) 1 d D U P A 1
H9 H 0.8242 0.5404 1.0471 0.106 Uiso 0.40(3) 1 calc R U P A 1
C10 C 0.799(2) 0.4597(17) 0.7026(9) 0.074(4) Uani 1 1 d . . . . .
C11 C 0.679(2) 0.2751(17) 0.6544(10) 0.081(4) Uani 1 1 d . . . . .
H11 H 0.5506 0.2837 0.6143 0.098 Uiso 1 1 calc R U . . .
C12 C 0.789(3) 0.195(2) 0.5910(11) 0.098(5) Uani 1 1 d . . . . .
H12A H 0.9149 0.1824 0.6304 0.118 Uiso 1 1 calc R U . . .
H12B H 0.7097 0.0814 0.5615 0.118 Uiso 1 1 calc R U . . .
C13 C 0.836(3) 0.283(2) 0.5162(11) 0.095(5) Uani 1 1 d . . . . .
H13 H 0.9112 0.3987 0.5485 0.113 Uiso 1 1 calc R U . . .
C14 C 0.981(4) 0.208(2) 0.4673(16) 0.150(9) Uani 1 1 d . . . . .
H14A H 0.9184 0.1744 0.4009 0.224 Uiso 1 1 calc R U . . .
H14B H 1.0102 0.1111 0.4928 0.224 Uiso 1 1 calc R U . . .
H14C H 1.1033 0.2927 0.4779 0.224 Uiso 1 1 calc R U . . .
C15 C 0.665(4) 0.306(3) 0.4453(13) 0.138(8) Uani 1 1 d . . . . .
H15A H 0.5767 0.1976 0.4162 0.207 Uiso 1 1 calc R U . . .
H15B H 0.7130 0.3592 0.3983 0.207 Uiso 1 1 calc R U . . .
H15C H 0.5941 0.3775 0.4748 0.207 Uiso 1 1 calc R U . . .
C2A C 1.018(3) 0.982(3) 1.0742(17) 0.075(8) Uani 0.60(3) 1 d . . P A 2
H2A H 1.0563 0.8805 1.0935 0.090 Uiso 0.60(3) 1 calc R U P A 2
C3A C 0.833(3) 0.933(3) 0.9871(16) 0.060(6) Uani 0.60(3) 1 d . . P A 2
H3A H 0.7332 0.9987 0.9943 0.072 Uiso 0.60(3) 1 calc R U P A 2
C4A C 0.732(3) 0.740(2) 0.9446(15) 0.047(5) Uani 0.60(3) 1 d D U P A 2
C5A C 0.574(4) 0.703(3) 0.8621(17) 0.054(6) Uani 0.60(3) 1 d D U P A 2
H5A H 0.5299 0.7902 0.8352 0.065 Uiso 0.60(3) 1 calc R U P A 2
C6A C 0.484(5) 0.536(3) 0.821(2) 0.096(15) Uani 0.60(3) 1 d D U P A 2
H6A H 0.3714 0.5146 0.7699 0.115 Uiso 0.60(3) 1 calc R U P A 2
C8A C 0.699(3) 0.441(3) 0.9410(16) 0.051(5) Uani 0.60(3) 1 d D U P A 2
H8A H 0.7397 0.3552 0.9702 0.061 Uiso 0.60(3) 1 calc R U P A 2
C9A C 0.780(3) 0.604(3) 0.9843(17) 0.063(6) Uani 0.60(3) 1 d D U P A 2
H9A H 0.8727 0.6261 1.0429 0.076 Uiso 0.60(3) 1 calc R U P A 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O5 1.425(14) . ?
S1 O6 1.436(12) . ?
S1 N1 1.596(15) . ?
S1 C7 1.741(15) . ?
O1 C1 1.233(15) . ?
O1 H20 0.8200 . ?
O2 C1 1.250(15) . ?
O3 C10 1.289(15) . ?
O3 H21 0.8200 . ?
O4 C10 1.241(15) . ?
N1 C11 1.429(17) . ?
N1 H22 0.8600 . ?
C1 C2A 1.51(3) . ?
C1 C2 1.66(4) . ?
C2 C3 1.32(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.43(4) . ?
C3 H3 0.9300 . ?
C4 C9 1.40(3) . ?
C4 C5 1.40(2) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.34(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.25(5) . ?
C7 C6A 1.42(3) . ?
C7 C8A 1.43(3) . ?
C8 C9 1.34(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.560(18) . ?
C11 C12 1.51(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.47(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.46(2) . ?
C13 C14 1.55(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2A C3A 1.55(3) . ?
C2A C3A 1.66(4) 2_777 ?
C2A H2A 0.9800 . ?
C3A C4A 1.57(3) . ?
C3A C2A 1.66(4) 2_777 ?
C3A H3A 0.9800 . ?
C4A C9A 1.39(2) . ?
C4A C5A 1.40(2) . ?
C5A C6A 1.37(2) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C8A C9A 1.35(3) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
 
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
O5 S1 O6 120.4(9) . . ?
O5 S1 N1 105.4(9) . . ?
O6 S1 N1 107.9(9) . . ?
O5 S1 C7 108.6(8) . . ?
O6 S1 C7 106.0(8) . . ?
N1 S1 C7 108.0(6) . . ?
C1 O1 H20 109.5 . . ?
C10 O3 H21 109.5 . . ?
C11 N1 S1 125.2(11) . . ?
C11 N1 H22 117.4 . . ?
S1 N1 H22 117.4 . . ?
O1 C1 O2 127.6(12) . . ?
O1 C1 C2A 115.2(14) . . ?
O2 C1 C2A 113.1(15) . . ?
O1 C1 C2 110.9(15) . . ?
O2 C1 C2 118.0(16) . . ?
C3 C2 C1 122(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 121(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C4 C5 117(2) . . ?
C9 C4 C3 131(3) . . ?
C5 C4 C3 112(3) . . ?
C6 C5 C4 120(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 114(2) . . ?
C7 C6 H6 123.0 . . ?
C5 C6 H6 123.0 . . ?
C8 C7 C6 132(3) . . ?
C6A C7 C8A 112.7(17) . . ?
C8 C7 S1 110(2) . . ?
C6 C7 S1 117.9(16) . . ?
C6A C7 S1 120.9(14) . . ?
C8A C7 S1 126.2(13) . . ?
C7 C8 C9 115(3) . . ?
C7 C8 H8 122.6 . . ?
C9 C8 H8 122.6 . . ?
C8 C9 C4 122(3) . . ?
C8 C9 H9 118.8 . . ?
C4 C9 H9 118.8 . . ?
O4 C10 O3 125.5(13) . . ?
O4 C10 C11 118.9(12) . . ?
O3 C10 C11 115.3(12) . . ?
N1 C11 C12 112.7(13) . . ?
N1 C11 C10 111.8(11) . . ?
C12 C11 C10 110.1(13) . . ?
N1 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C10 C11 H11 107.3 . . ?
C13 C12 C11 117.7(14) . . ?
C13 C12 H12A 107.9 . . ?
C11 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
C11 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C15 C13 C12 116.7(18) . . ?
C15 C13 C14 109.8(15) . . ?
C12 C13 C14 113.2(15) . . ?
C15 C13 H13 105.4 . . ?
C12 C13 H13 105.4 . . ?
C14 C13 H13 105.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2A C3A 114.0(17) . . ?
C1 C2A C3A 118.0(16) . 2_777 ?
C3A C2A C3A 92.0(18) . 2_777 ?
C1 C2A H2A 110.5 . . ?
C3A C2A H2A 110.5 . . ?
C3A C2A H2A 110.5 2_777 . ?
C2A C3A C4A 120.3(17) . . ?
C2A C3A C2A 88.0(18) . 2_777 ?
C4A C3A C2A 112.3(16) . 2_777 ?
C2A C3A H3A 111.4 . . ?
C4A C3A H3A 111.4 . . ?
C2A C3A H3A 111.4 2_777 . ?
C9A C4A C5A 117.2(16) . . ?
C9A C4A C3A 125.1(17) . . ?
C5A C4A C3A 117.6(15) . . ?
C6A C5A C4A 119.5(17) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C7 124(2) . . ?
C5A C6A H6A 117.8 . . ?
C7 C6A H6A 117.8 . . ?
C9A C8A C7 122.6(18) . . ?
C9A C8A H8A 118.7 . . ?
C7 C8A H8A 118.7 . . ?
C8A C9A C4A 122.5(18) . . ?
C8A C9A H9A 118.7 . . ?
C4A C9A H9A 118.7 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O5 S1 N1 C11 180.0(12) . . . . ?
O6 S1 N1 C11 50.1(13) . . . . ?
C7 S1 N1 C11 -64.1(13) . . . . ?
O1 C1 C2 C3 169(3) . . . . ?
O2 C1 C2 C3 8(3) . . . . ?
C2A C1 C2 C3 -86(3) . . . . ?
C1 C2 C3 C4 172(3) . . . . ?
C2 C3 C4 C9 11(6) . . . . ?
C2 C3 C4 C5 -167(3) . . . . ?
C9 C4 C5 C6 -1(2) . . . . ?
C3 C4 C5 C6 178(3) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C5 C6 C7 C8 -2(5) . . . . ?
C5 C6 C7 C6A -15(58) . . . . ?
C5 C6 C7 C8A -6(3) . . . . ?
C5 C6 C7 S1 179.4(14) . . . . ?
O5 S1 C7 C8 29(3) . . . . ?
O6 S1 C7 C8 159(3) . . . . ?
N1 S1 C7 C8 -85(3) . . . . ?
O5 S1 C7 C6 -153(2) . . . . ?
O6 S1 C7 C6 -22(2) . . . . ?
N1 S1 C7 C6 94(2) . . . . ?
O5 S1 C7 C6A -154(2) . . . . ?
O6 S1 C7 C6A -23(2) . . . . ?
N1 S1 C7 C6A 93(2) . . . . ?
O5 S1 C7 C8A 33.0(17) . . . . ?
O6 S1 C7 C8A 163.7(15) . . . . ?
N1 S1 C7 C8A -80.9(15) . . . . ?
C6 C7 C8 C9 3(7) . . . . ?
C6A C7 C8 C9 3(7) . . . . ?
C8A C7 C8 C9 14(8) . . . . ?
S1 C7 C8 C9 -179(3) . . . . ?
C7 C8 C9 C4 -2(6) . . . . ?
C5 C4 C9 C8 1(5) . . . . ?
C3 C4 C9 C8 -177(4) . . . . ?
S1 N1 C11 C12 -162.6(11) . . . . ?
S1 N1 C11 C10 72.8(16) . . . . ?
O4 C10 C11 N1 -136.8(15) . . . . ?
O3 C10 C11 N1 48.8(18) . . . . ?
O4 C10 C11 C12 97.1(16) . . . . ?
O3 C10 C11 C12 -77.3(16) . . . . ?
N1 C11 C12 C13 177.6(14) . . . . ?
C10 C11 C12 C13 -56.8(18) . . . . ?
C11 C12 C13 C15 -61(2) . . . . ?
C11 C12 C13 C14 169.8(15) . . . . ?
O1 C1 C2A C3A 161.4(17) . . . . ?
O2 C1 C2A C3A -39(2) . . . . ?
C2 C1 C2A C3A 67(2) . . . . ?
O1 C1 C2A C3A -92(2) . . . 2_777 ?
O2 C1 C2A C3A 67(2) . . . 2_777 ?
C2 C1 C2A C3A 174(3) . . . 2_777 ?
C1 C2A C3A C4A -123.2(19) . . . . ?
C3A C2A C3A C4A 115(2) 2_777 . . . ?
C1 C2A C3A C2A 122(2) . . . 2_777 ?
C3A C2A C3A C2A 0.000(1) 2_777 . . 2_777 ?
C2A C3A C4A C9A 7(3) . . . . ?
C2A C3A C4A C9A 108(2) 2_777 . . . ?
C2A C3A C4A C5A -176(2) . . . . ?
C2A C3A C4A C5A -75(2) 2_777 . . . ?
C9A C4A C5A C6A -4.1(18) . . . . ?
C3A C4A C5A C6A 178(2) . . . . ?
C4A C5A C6A C7 -6(3) . . . . ?
C8 C7 C6A C5A 15(5) . . . . ?
C6 C7 C6A C5A -178(100) . . . . ?
C8A C7 C6A C5A 11(4) . . . . ?
S1 C7 C6A C5A -163.0(18) . . . . ?
C8 C7 C8A C9A -179(12) . . . . ?
C6 C7 C8A C9A -8(3) . . . . ?
C6A C7 C8A C9A -7(3) . . . . ?
S1 C7 C8A C9A 166.5(17) . . . . ?
C7 C8A C9A C4A -2(3) . . . . ?
C5A C4A C9A C8A 8(3) . . . . ?
C3A C4A C9A C8A -175(2) . . . . ?
 
_refine_diff_density_max    0.412
_refine_diff_density_min   -0.355
_refine_diff_density_rms    0.099

_shelxl_version_number 2013-4



 

#==END

 
data_kaw115 
# rac-4 unreacted

 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C14 H17 N O6 S2'  
_chemical_formula_sum 
 'C14 H17 N O6 S2' 
_chemical_formula_weight          359.41 
 
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' 
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
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                    8.2440(3) 
_cell_length_b                    7.4617(3) 
_cell_length_c                    27.2752(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.372(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1667.45(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3643
_cell_measurement_theta_min       3.251
_cell_measurement_theta_max       65.58
 
_exptl_crystal_description        'transparent plate'
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.31 
_exptl_crystal_size_mid           0.29 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.432 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              752 
_exptl_absorpt_coefficient_mu     3.168 
_exptl_absorpt_correction_type    'multi-scan'
_shelx_estimated_absorpt_T_min    0.435
_shelx_estimated_absorpt_T_max    0.790
_exptl_absorpt_correction_T_min   0.4352 
_exptl_absorpt_correction_T_max   0.7902 
_exptl_absorpt_process_details    
      'SADABS (Bruker, 2010)'
_exptl_special_details 
; 
 The data collection was performed under ambient condition to
 reduce the impact of thermal shock on the sample.  The
 quality of the crystal becomes important when processing the 
 sample with UV radiation and subsequent data collections
 on the same sample. 
; 
 
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             20611
_diffrn_reflns_av_unetI/netI      0.0355
_diffrn_reflns_av_R_equivalents   0.0624
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -32
_diffrn_reflns_limit_l_max        32
_diffrn_reflns_theta_min          3.261
_diffrn_reflns_theta_max          67.809
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3003
_reflns_number_gt                 2260
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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 
; 
Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
_reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with O/N-H bond distances
 of 0.85(2) angstroms.


; 
 

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0664P)²+0.9405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3003
_refine_ls_number_parameters      219
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0696
_refine_ls_R_factor_gt            0.0511
_refine_ls_wR_factor_ref          0.1398
_refine_ls_wR_factor_gt           0.1289
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_restrained_S_all       1.033
_refine_ls_shift/su_max           0.004
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.65778(9) 0.94477(11) 0.13398(3) 0.0539(2) Uani 1 1 d . . . . .
S2 S 1.06656(12) 0.35449(14) 0.24639(3) 0.0704(3) Uani 1 1 d . . . . .
O1 O -0.2817(3) 0.6824(4) -0.03483(9) 0.0702(7) Uani 1 1 d D . . . .
H20 H -0.369(3) 0.649(5) -0.0512(13) 0.084 Uiso 1 1 d D U . . .
O2 O -0.1636(3) 0.6001(4) -0.10025(9) 0.0801(8) Uani 1 1 d . . . . .
O3 O 0.4421(3) 0.5173(4) 0.14705(9) 0.0707(7) Uani 1 1 d D . . . .
H21 H 0.349(3) 0.490(5) 0.1317(13) 0.085 Uiso 1 1 d D U . . .
O4 O 0.5664(3) 0.4245(3) 0.08352(9) 0.0692(7) Uani 1 1 d . . . . .
O5 O 0.6334(3) 1.0845(3) 0.16793(9) 0.0664(6) Uani 1 1 d . . . . .
O6 O 0.7839(3) 0.9596(4) 0.10250(9) 0.0742(7) Uani 1 1 d . . . . .
N1 N 0.6943(3) 0.7677(4) 0.16824(9) 0.0538(6) Uani 1 1 d D . . . .
H22 H 0.634(4) 0.764(5) 0.1913(10) 0.065 Uiso 1 1 d D U . . .
C1 C -0.1561(4) 0.6621(4) -0.05791(12) 0.0570(8) Uani 1 1 d . . . . .
C2 C 0.0040(4) 0.7132(5) -0.03274(12) 0.0590(8) Uani 1 1 d . . . . .
H2 H 0.0973 0.6992 -0.0500 0.071 Uiso 1 1 calc R U . . .
C3 C 0.0247(4) 0.7773(4) 0.01242(11) 0.0530(7) Uani 1 1 d . . . . .
H3 H -0.0704 0.7942 0.0286 0.064 Uiso 1 1 calc R U . . .
C4 C 0.1819(4) 0.8252(4) 0.04004(11) 0.0486(7) Uani 1 1 d . . . . .
C5 C 0.1829(4) 0.8882(5) 0.08806(11) 0.0541(8) Uani 1 1 d . . . . .
H5 H 0.0826 0.9028 0.1017 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3272(4) 0.9299(4) 0.11617(11) 0.0546(8) Uani 1 1 d . . . . .
H6 H 0.3267 0.9737 0.1489 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4731(3) 0.9072(4) 0.09614(11) 0.0483(7) Uani 1 1 d . . . . .
C8 C 0.4750(4) 0.8475(5) 0.04842(11) 0.0558(8) Uani 1 1 d . . . . .
H8 H 0.5755 0.8340 0.0348 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3295(4) 0.8073(5) 0.02060(11) 0.0571(8) Uani 1 1 d . . . . .
H9 H 0.3304 0.7668 -0.0124 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5651(4) 0.5054(4) 0.12286(12) 0.0553(8) Uani 1 1 d . . . . .
C11 C 0.7212(4) 0.5956(4) 0.14598(13) 0.0605(9) Uani 1 1 d . . . . .
H11 H 0.7958 0.6128 0.1199 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8031(4) 0.4660(5) 0.18534(16) 0.0745(11) Uani 1 1 d . . . . .
H12A H 0.7349 0.4586 0.2129 0.089 Uiso 1 1 calc R U . . .
H12B H 0.8071 0.3450 0.1707 0.089 Uiso 1 1 calc R U . . .
C13 C 0.9725(4) 0.5200(5) 0.20546(14) 0.0711(10) Uani 1 1 d . . . . .
H13A H 0.9682 0.6353 0.2233 0.085 Uiso 1 1 calc R U . . .
H13B H 1.0391 0.5380 0.1778 0.085 Uiso 1 1 calc R U . . .
C14 C 1.0794(7) 0.1649(7) 0.20747(17) 0.1135(19) Uani 1 1 d . . . . .
H14A H 0.9696 0.1312 0.1929 0.170 Uiso 1 1 calc R U . . .
H14B H 1.1288 0.0646 0.2269 0.170 Uiso 1 1 calc R U . . .
H14C H 1.1467 0.1946 0.1812 0.170 Uiso 1 1 calc R U . . .
 
 
_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 O5 1.423(2) . ?
S1 O6 1.424(2) . ?
S1 N1 1.627(3) . ?
S1 C7 1.764(3) . ?
S2 C14 1.779(5) . ?
S2 C13 1.784(4) . ?
O1 C1 1.279(4) . ?
O1 H20 0.840(19) . ?
O2 C1 1.239(4) . ?
O3 C10 1.273(4) . ?
O3 H21 0.858(19) . ?
O4 C10 1.232(4) . ?
N1 C11 1.448(4) . ?
N1 H22 0.845(18) . ?
C1 C2 1.469(4) . ?
C2 C3 1.315(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.468(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.387(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(4) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.526(5) . ?
C11 C12 1.544(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.498(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O5 S1 O6 120.05(15) . . ?
O5 S1 N1 104.57(14) . . ?
O6 S1 N1 107.95(15) . . ?
O5 S1 C7 108.78(14) . . ?
O6 S1 C7 107.45(15) . . ?
N1 S1 C7 107.44(14) . . ?
C14 S2 C13 103.16(19) . . ?
C1 O1 H20 113(3) . . ?
C10 O3 H21 117(3) . . ?
C11 N1 S1 120.4(2) . . ?
C11 N1 H22 115(3) . . ?
S1 N1 H22 111(2) . . ?
O2 C1 O1 122.9(3) . . ?
O2 C1 C2 118.8(3) . . ?
O1 C1 C2 118.3(3) . . ?
C3 C2 C1 123.3(3) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 125.8(3) . . ?
C2 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
C9 C4 C5 118.6(3) . . ?
C9 C4 C3 122.8(3) . . ?
C5 C4 C3 118.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 S1 120.3(2) . . ?
C6 C7 S1 118.7(2) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O4 C10 O3 124.8(3) . . ?
O4 C10 C11 119.2(3) . . ?
O3 C10 C11 116.0(3) . . ?
N1 C11 C10 113.8(3) . . ?
N1 C11 C12 109.8(3) . . ?
C10 C11 C12 107.1(3) . . ?
N1 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 S2 111.5(3) . . ?
C12 C13 H13A 109.3 . . ?
S2 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
S2 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O5 S1 N1 C11 178.3(2) . . . . ?
O6 S1 N1 C11 -52.8(3) . . . . ?
C7 S1 N1 C11 62.8(3) . . . . ?
O2 C1 C2 C3 -178.8(3) . . . . ?
O1 C1 C2 C3 0.6(5) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C9 0.1(5) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
C9 C4 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C5 C6 C7 S1 -175.2(3) . . . . ?
O5 S1 C7 C8 149.8(3) . . . . ?
O6 S1 C7 C8 18.4(3) . . . . ?
N1 S1 C7 C8 -97.5(3) . . . . ?
O5 S1 C7 C6 -33.5(3) . . . . ?
O6 S1 C7 C6 -164.9(3) . . . . ?
N1 S1 C7 C6 79.1(3) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
S1 C7 C8 C9 175.6(3) . . . . ?
C7 C8 C9 C4 -0.4(5) . . . . ?
C5 C4 C9 C8 1.3(5) . . . . ?
C3 C4 C9 C8 -177.6(3) . . . . ?
S1 N1 C11 C10 -77.0(4) . . . . ?
S1 N1 C11 C12 162.9(2) . . . . ?
O4 C10 C11 N1 140.8(3) . . . . ?
O3 C10 C11 N1 -40.6(4) . . . . ?
O4 C10 C11 C12 -97.6(4) . . . . ?
O3 C10 C11 C12 81.0(4) . . . . ?
N1 C11 C12 C13 -66.0(4) . . . . ?
C10 C11 C12 C13 169.9(3) . . . . ?
C11 C12 C13 S2 -174.6(3) . . . . ?
C14 S2 C13 C12 63.7(4) . . . . ?
 
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 H20 O4  0.840(19) 1.847(19) 2.686(3) 176(4) 3_565
O3 H21 O2  0.858(19) 1.80(2) 2.649(3) 172(4) 3_565
N1 H22 S2  0.845(18) 2.59(2) 3.403(3) 162(3) 2_655
 
_refine_diff_density_max    0.532
_refine_diff_density_min   -0.252
_refine_diff_density_rms    0.049

_shelxl_version_number 2013-4



#==END

 
data_kaw116c 
# rac-4 UV irradiated
 
# start Validation Reply Form
_vrf_SHFSU01_kaw116c
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: ...
;
_vrf_PLAT080_kaw116c
;
PROBLEM: Maximum Shift/Error ............................       0.16       
RESPONSE: Excessive shift due to effects of disorder and 
crystal degradation from UV exposure of sample.
;
_vrf_PLAT213_kaw116c
;
PROBLEM: Atom O5A             has ADP max/min Ratio .....        4.6 prolat
RESPONSE: Atom O5 ADP issues due to effects of disorder and 
crystal degradation from UV exposure of sample.
;
_vrf_PLAT220_kaw116c
;
PROBLEM: Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        4.4 Ratio 
RESPONSE: Due to effects of disorder and 
crystal degradation from UV exposure of sample.
;
_vrf_PLAT230_kaw116c
;
PROBLEM: Hirshfeld Test Diff for    O3     --  C10     ..       11.0 su    
RESPONSE: Due to effects of disorder and 
crystal degradation from UV exposure of sample.
;
# end Validation Reply Form


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C14 H17 N O6 S2'
_chemical_formula_sum 
 'C14 H17 N O6 S2' 
_chemical_formula_weight          359.41 
 
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' 
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
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                    8.0832(2) 
_cell_length_b                    7.1669(2) 
_cell_length_c                    27.7096(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.214(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      1595.83(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     3606 
_cell_measurement_theta_min       3.208
_cell_measurement_theta_max       65.115
 
_exptl_crystal_description        'transparent plate'
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.314
_exptl_crystal_size_mid           0.289
_exptl_crystal_size_min           0.078
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.496 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              752 
_exptl_absorpt_coefficient_mu     3.310 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.4229 
_exptl_absorpt_correction_T_max   0.7823 
_exptl_absorpt_process_details    
      'SADABS (Bruker, 2010)'
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             21047
_diffrn_reflns_av_unetI/netI      0.0521
_diffrn_reflns_av_R_equivalents   0.0818
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -33
_diffrn_reflns_limit_l_max        33
_diffrn_reflns_theta_min          3.208
_diffrn_reflns_theta_max          67.711
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              2882
_reflns_number_gt                 2294
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_computing_data_collection        'APEX2'
_computing_cell_refinement        'APEX2'
_computing_data_reduction         
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material   'XSEED (Barbour, 2001)'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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 a difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with O/N-H bond distances
 of 0.85(2) angstroms.

This crystal was illuminated for 45 hrs via 200 W Xe(Hg) arc lamp.  Solution
 and refinement of the data revealed 64% photoproduct and 36% starting olefin
 via refinement of occupancy factors.  The aryl ring of the olefin component
 was restrained to match the conformation of the phenyl group of the product
 using the SAME command in shelxl. 
; 
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0455P)²+1.8946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2882
_refine_ls_number_parameters      358
_refine_ls_number_restraints      55
_refine_ls_R_factor_all           0.0714
_refine_ls_R_factor_gt            0.0553
_refine_ls_wR_factor_ref          0.1402
_refine_ls_wR_factor_gt           0.1315
_refine_ls_goodness_of_fit_ref    1.117
_refine_ls_restrained_S_all       1.115
_refine_ls_shift/su_max           0.157
_refine_ls_shift/su_mean          0.006
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.6508(7) 0.0465(8) 0.1281(2) 0.0665(18) Uani 0.638(6) 1 d . . P A 1
S2 S 1.04930(14) 0.65696(13) 0.24833(3) 0.0545(3) Uani 1 1 d . . . . .
O1 O -0.2892(3) 0.3101(3) -0.03731(9) 0.0444(6) Uani 1 1 d D . . . .
O2 O -0.1761(3) 0.3709(4) -0.10541(9) 0.0516(7) Uani 1 1 d . . . . .
O3 O 0.4592(4) 0.4988(3) 0.14929(10) 0.0539(7) Uani 1 1 d D . . . .
O4 O 0.5773(3) 0.5919(4) 0.08445(9) 0.0554(7) Uani 1 1 d D . . . .
O5 O 0.615(3) -0.091(2) 0.1602(6) 0.057(4) Uani 0.638(6) 1 d . . P A 1
O6 O 0.7746(19) 0.0216(19) 0.0959(6) 0.080(4) Uani 0.638(6) 1 d . . P A 1
N1 N 0.692(2) 0.2086(17) 0.1667(7) 0.045(3) Uani 0.638(6) 1 d D . P A 1
C1 C -0.1658(4) 0.3459(5) -0.06101(12) 0.0432(8) Uani 1 1 d . . . . .
C2 C -0.0095(6) 0.4166(7) -0.03359(16) 0.0316(12) Uani 0.638(6) 1 d . . P A 1
H2 H 0.0910 0.3809 -0.0496 0.026(12) Uiso 0.638(6) 1 calc R . P A 1
C3 C 0.0114(6) 0.3681(6) 0.02150(16) 0.0299(12) Uani 0.638(6) 1 d . . P A 1
H3 H -0.0916 0.3068 0.0308 0.036 Uiso 0.638(6) 1 calc R U P A 1
C4 C 0.1636(7) 0.2628(9) 0.04268(19) 0.0295(13) Uani 0.638(6) 1 d D . P A 1
C5 C 0.3100(9) 0.2616(11) 0.0213(3) 0.0371(17) Uani 0.638(6) 1 d D . P A 1
H5 H 0.3135 0.3131 -0.0102 0.045 Uiso 0.638(6) 1 calc R U P A 1
C6 C 0.4533(14) 0.1841(19) 0.0462(5) 0.038(3) Uani 0.638(6) 1 d D . P A 1
H6 H 0.5541 0.1817 0.0315 0.046 Uiso 0.638(6) 1 calc R U P A 1
C7 C 0.4488(18) 0.112(3) 0.0917(6) 0.036(4) Uani 0.638(6) 1 d D . P A 1
C8 C 0.3020(15) 0.1061(16) 0.1133(4) 0.029(3) Uani 0.638(6) 1 d D . P A 1
H8 H 0.2991 0.0540 0.1447 0.035 Uiso 0.638(6) 1 calc R U P A 1
C9 C 0.1602(14) 0.1787(11) 0.0878(3) 0.033(2) Uani 0.638(6) 1 d D . P A 1
H9 H 0.0575 0.1709 0.1015 0.040 Uiso 0.638(6) 1 calc R U P A 1
C10 C 0.5786(5) 0.5038(5) 0.12260(14) 0.0448(8) Uani 1 1 d . . . . .
C11 C 0.730(2) 0.385(2) 0.1455(5) 0.074(6) Uani 0.638(6) 1 d . . P A 1
H11 H 0.8098 0.3648 0.1207 0.089 Uiso 0.638(6) 1 calc R U P A 1
C12 C 0.8102(9) 0.5396(9) 0.1861(4) 0.059(2) Uani 0.638(6) 1 d . . P A 1
H12B H 0.8191 0.6623 0.1702 0.071 Uiso 0.638(6) 1 calc R U P A 1
H12A H 0.7352 0.5536 0.2118 0.071 Uiso 0.638(6) 1 calc R U P A 1
C13 C 0.9748(9) 0.4810(9) 0.2078(2) 0.060(2) Uani 0.638(6) 1 d . . P A 1
H13A H 1.0506 0.4641 0.1824 0.072 Uiso 0.638(6) 1 calc R U P A 1
H13B H 0.9669 0.3613 0.2253 0.072 Uiso 0.638(6) 1 calc R U P A 1
C14 C 1.0521(6) 0.8660(6) 0.21255(16) 0.0706(13) Uani 1 1 d . . . . .
H14A H 1.1400 0.9492 0.2270 0.106 Uiso 1 1 calc R U . . .
H14B H 0.9442 0.9290 0.2117 0.106 Uiso 1 1 calc R U . . .
H14C H 1.0736 0.8336 0.1794 0.106 Uiso 1 1 calc R U . . .
H20 H -0.381(4) 0.335(7) -0.0536(16) 0.085 Uiso 1 1 d D U . . .
H21 H 0.377(3) 0.564(5) 0.1410(11) 0.085 Uiso 1 1 d D U . . .
H22 H 0.628(8) 0.236(12) 0.189(2) 0.085 Uiso 0.638(6) 1 d D U P A 1
S1A S 0.6380(8) 0.0313(9) 0.1314(2) 0.0234(13) Uani 0.362(6) 1 d D U P A 2
O5A O 0.601(4) -0.112(3) 0.1687(10) 0.033(3) Uani 0.362(6) 1 d . U P A 2
O6A O 0.761(3) -0.004(2) 0.1007(9) 0.043(4) Uani 0.362(6) 1 d . U P A 2
N1A N 0.702(4) 0.241(3) 0.1607(11) 0.038(4) Uani 0.362(6) 1 d D U P A 2
H22A H 0.780(9) 0.206(7) 0.182(3) 0.045 Uiso 0.362(6) 1 d D U P A 2
C2A C 0.0035(12) 0.2702(17) -0.0329(3) 0.045(3) Uani 0.362(6) 1 d . . P A 2
H2A H 0.0997 0.2701 -0.0497 0.053 Uiso 0.362(6) 1 calc R U P A 2
C3A C 0.0198(11) 0.2062(13) 0.0133(3) 0.039(2) Uani 0.362(6) 1 d . . P A 2
H3A H -0.0787 0.1892 0.0286 0.046 Uiso 0.362(6) 1 calc R U P A 2
C4A C 0.1785(11) 0.1613(19) 0.0412(3) 0.033(2) Uani 0.362(6) 1 d D . P A 2
C5A C 0.3294(14) 0.1723(19) 0.0224(4) 0.036(3) Uani 0.362(6) 1 d D . P A 2
H5A H 0.3320 0.2100 -0.0104 0.043 Uiso 0.362(6) 1 calc R U P A 2
C6A C 0.478(2) 0.130(3) 0.0504(8) 0.033(5) Uani 0.362(6) 1 d D . P A 2
H6A H 0.5809 0.1393 0.0371 0.039 Uiso 0.362(6) 1 calc R U P A 2
C7A C 0.473(2) 0.073(5) 0.0976(9) 0.024(4) Uani 0.362(6) 1 d D . P A 2
C8A C 0.321(2) 0.054(3) 0.1163(7) 0.025(4) Uani 0.362(6) 1 d D . P A 2
H8A H 0.3180 0.0038 0.1479 0.030 Uiso 0.362(6) 1 calc R U P A 2
C9A C 0.174(2) 0.107(2) 0.0893(4) 0.028(3) Uani 0.362(6) 1 d D . P A 2
H9A H 0.0724 0.1071 0.1034 0.034 Uiso 0.362(6) 1 calc R U P A 2
C11A C 0.735(3) 0.404(3) 0.1350(8) 0.031(3) Uani 0.362(6) 1 d . U P A 2
H11A H 0.7707 0.3602 0.1035 0.037 Uiso 0.362(6) 1 calc R U P A 2
C12A C 0.8862(9) 0.4870(10) 0.1626(3) 0.0199(18) Uani 0.362(6) 1 d . U P A 2
H12D H 0.9203 0.5992 0.1453 0.024 Uiso 0.362(6) 1 calc R U P A 2
H12C H 0.9788 0.3959 0.1643 0.024 Uiso 0.362(6) 1 calc R U P A 2
C13A C 0.8508(9) 0.5422(10) 0.2156(3) 0.0164(17) Uani 0.362(6) 1 d . U P A 2
H13C H 0.8214 0.4297 0.2336 0.020 Uiso 0.362(6) 1 calc R U P A 2
H13D H 0.7564 0.6307 0.2142 0.020 Uiso 0.362(6) 1 calc R U P A 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O5 1.376(13) . ?
S1 O6 1.422(13) . ?
S1 N1 1.589(19) . ?
S1 C7 1.883(14) . ?
S2 C13 1.751(6) . ?
S2 C14 1.798(4) . ?
S2 C13A 1.939(8) . ?
O1 C1 1.279(4) . ?
O1 H20 0.85(2) . ?
O2 C1 1.237(4) . ?
O3 C10 1.278(5) . ?
O3 H21 0.82(2) . ?
O4 C10 1.231(4) . ?
N1 C11 1.443(15) . ?
N1 H22 0.87(2) . ?
C1 C2 1.490(6) . ?
C1 C2A 1.595(10) . ?
C2 C3 1.557(6) . ?
C2 C3 1.580(7) 3_565 ?
C2 H2 1.0000 . ?
C3 C4 1.507(8) . ?
C3 C2 1.580(7) 3_565 ?
C3 H3 1.0000 . ?
C4 C5 1.380(8) . ?
C4 C9 1.391(9) . ?
C5 C6 1.397(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.367(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(10) . ?
C8 C9 1.382(10) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11A 1.46(2) . ?
C10 C11 1.570(17) . ?
C11 C12 1.657(18) . ?
C11 H11 1.0000 . ?
C12 C13 1.461(10) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1A O6A 1.404(17) . ?
S1A O5A 1.51(2) . ?
S1A C7A 1.57(2) . ?
S1A N1A 1.76(3) . ?
N1A C11A 1.41(3) . ?
N1A H22A 0.86(2) . ?
C2A C3A 1.351(13) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.461(12) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.380(12) . ?
C4A C9A 1.391(13) . ?
C5A C6A 1.390(14) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.374(14) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.388(13) . ?
C8A C9A 1.387(14) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C11A C12A 1.49(3) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.577(10) . ?
C12A H12D 0.9900 . ?
C12A H12C 0.9900 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
 
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
O5 S1 O6 121.7(11) . . ?
O5 S1 N1 97.6(10) . . ?
O6 S1 N1 113.7(9) . . ?
O5 S1 C7 107.1(11) . . ?
O6 S1 C7 108.8(9) . . ?
N1 S1 C7 106.6(10) . . ?
C13 S2 C14 105.7(3) . . ?
C14 S2 C13A 98.9(3) . . ?
C1 O1 H20 112(3) . . ?
C10 O3 H21 117.2(16) . . ?
C11 N1 S1 114.0(13) . . ?
C11 N1 H22 105(6) . . ?
S1 N1 H22 123(6) . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C2 114.8(4) . . ?
O1 C1 C2 118.2(3) . . ?
O2 C1 C2A 119.8(5) . . ?
O1 C1 C2A 110.9(5) . . ?
C1 C2 C3 114.8(4) . . ?
C1 C2 C3 114.4(4) . 3_565 ?
C3 C2 C3 90.7(4) . 3_565 ?
C1 C2 H2 111.8 . . ?
C3 C2 H2 111.8 . . ?
C3 C2 H2 111.8 3_565 . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 C2 115.7(4) . 3_565 ?
C2 C3 C2 89.3(4) . 3_565 ?
C4 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
C2 C3 H3 110.3 3_565 . ?
C5 C4 C9 119.0(7) . . ?
C5 C4 C3 122.5(5) . . ?
C9 C4 C3 118.2(6) . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.2(9) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.2(10) . . ?
C6 C7 S1 118.7(10) . . ?
C8 C7 S1 119.6(9) . . ?
C9 C8 C7 118.0(9) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C4 121.8(8) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O4 C10 O3 125.1(3) . . ?
O4 C10 C11A 112.4(10) . . ?
O3 C10 C11A 122.5(10) . . ?
O4 C10 C11 124.0(7) . . ?
O3 C10 C11 110.9(7) . . ?
N1 C11 C10 116.5(13) . . ?
N1 C11 C12 113.3(11) . . ?
C10 C11 C12 98.2(10) . . ?
N1 C11 H11 109.5 . . ?
C10 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C13 C12 C11 111.0(8) . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
H12B C12 H12A 108.0 . . ?
C12 C13 S2 107.0(5) . . ?
C12 C13 H13A 110.3 . . ?
S2 C13 H13A 110.3 . . ?
C12 C13 H13B 110.3 . . ?
S2 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6A S1A O5A 119.9(14) . . ?
O6A S1A C7A 106.5(14) . . ?
O5A S1A C7A 108.6(16) . . ?
O6A S1A N1A 104.1(14) . . ?
O5A S1A N1A 109.6(14) . . ?
C7A S1A N1A 107.6(17) . . ?
C11A N1A S1A 122(2) . . ?
C11A N1A H22A 115(7) . . ?
S1A N1A H22A 103(3) . . ?
C3A C2A C1 124.7(8) . . ?
C3A C2A H2A 117.7 . . ?
C1 C2A H2A 117.7 . . ?
C2A C3A C4A 124.5(9) . . ?
C2A C3A H3A 117.7 . . ?
C4A C3A H3A 117.7 . . ?
C5A C4A C9A 119.5(10) . . ?
C5A C4A C3A 123.3(9) . . ?
C9A C4A C3A 117.3(10) . . ?
C4A C5A C6A 121.4(12) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C7A C6A C5A 119.0(15) . . ?
C7A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
C6A C7A C8A 120.0(16) . . ?
C6A C7A S1A 120.9(14) . . ?
C8A C7A S1A 119.1(15) . . ?
C9A C8A C7A 120.8(14) . . ?
C9A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
C8A C9A C4A 119.0(12) . . ?
C8A C9A H9A 120.5 . . ?
C4A C9A H9A 120.5 . . ?
N1A C11A C10 109(2) . . ?
N1A C11A C12A 105.2(19) . . ?
C10 C11A C12A 124.3(13) . . ?
N1A C11A H11A 105.7 . . ?
C10 C11A H11A 105.8 . . ?
C12A C11A H11A 105.8 . . ?
C11A C12A C13A 110.8(11) . . ?
C11A C12A H12D 109.5 . . ?
C13A C12A H12D 109.5 . . ?
C11A C12A H12C 109.5 . . ?
C13A C12A H12C 109.5 . . ?
H12D C12A H12C 108.1 . . ?
C12A C13A S2 108.5(5) . . ?
C12A C13A H13C 110.0 . . ?
S2 C13A H13C 110.0 . . ?
C12A C13A H13D 110.0 . . ?
S2 C13A H13D 110.0 . . ?
H13C C13A H13D 108.4 . . ?
 
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
O5 S1 N1 C11 -177.6(15) . . . . ?
O6 S1 N1 C11 52.8(16) . . . . ?
C7 S1 N1 C11 -67.1(14) . . . . ?
O2 C1 C2 C3 -174.3(4) . . . . ?
O1 C1 C2 C3 22.6(6) . . . . ?
C2A C1 C2 C3 -66.8(7) . . . . ?
O2 C1 C2 C3 82.7(5) . . . 3_565 ?
O1 C1 C2 C3 -80.4(5) . . . 3_565 ?
C2A C1 C2 C3 -169.8(8) . . . 3_565 ?
C1 C2 C3 C4 123.2(5) . . . . ?
C3 C2 C3 C4 -119.3(5) 3_565 . . . ?
C1 C2 C3 C2 -117.4(5) . . . 3_565 ?
C3 C2 C3 C2 0.002(0) 3_565 . . 3_565 ?
C2 C3 C4 C5 22.9(8) . . . . ?
C2 C3 C4 C5 -81.9(7) 3_565 . . . ?
C2 C3 C4 C9 -163.3(6) . . . . ?
C2 C3 C4 C9 91.9(7) 3_565 . . . ?
C9 C4 C5 C6 -3.0(12) . . . . ?
C3 C4 C5 C6 170.8(8) . . . . ?
C4 C5 C6 C7 -0.7(19) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C5 C6 C7 S1 -169.7(12) . . . . ?
O5 S1 C7 C6 -154.0(16) . . . . ?
O6 S1 C7 C6 -21(2) . . . . ?
N1 S1 C7 C6 102.4(17) . . . . ?
O5 S1 C7 C8 33(2) . . . . ?
O6 S1 C7 C8 166.8(15) . . . . ?
N1 S1 C7 C8 -70.2(18) . . . . ?
C6 C7 C8 C9 -1(3) . . . . ?
S1 C7 C8 C9 171.4(11) . . . . ?
C7 C8 C9 C4 -2.8(17) . . . . ?
C5 C4 C9 C8 4.8(11) . . . . ?
C3 C4 C9 C8 -169.2(8) . . . . ?
S1 N1 C11 C10 79.0(16) . . . . ?
S1 N1 C11 C12 -168.2(12) . . . . ?
O4 C10 C11 N1 -139.9(11) . . . . ?
O3 C10 C11 N1 41.3(15) . . . . ?
C11A C10 C11 N1 -136(7) . . . . ?
O4 C10 C11 C12 98.9(9) . . . . ?
O3 C10 C11 C12 -79.9(9) . . . . ?
C11A C10 C11 C12 103(7) . . . . ?
N1 C11 C12 C13 67.0(15) . . . . ?
C10 C11 C12 C13 -169.5(8) . . . . ?
C11 C12 C13 S2 178.1(7) . . . . ?
C14 S2 C13 C12 -58.5(6) . . . . ?
C13A S2 C13 C12 24.7(5) . . . . ?
O6A S1A N1A C11A 55(3) . . . . ?
O5A S1A N1A C11A -176(3) . . . . ?
C7A S1A N1A C11A -58(3) . . . . ?
O2 C1 C2A C3A -167.4(8) . . . . ?
O1 C1 C2A C3A -10.6(12) . . . . ?
C2 C1 C2A C3A 98.7(12) . . . . ?
C1 C2A C3A C4A -171.1(9) . . . . ?
C2A C3A C4A C5A -2.9(19) . . . . ?
C2A C3A C4A C9A 176.3(12) . . . . ?
C9A C4A C5A C6A 0(2) . . . . ?
C3A C4A C5A C6A 179.5(15) . . . . ?
C4A C5A C6A C7A 1(3) . . . . ?
C5A C6A C7A C8A 2(4) . . . . ?
C5A C6A C7A S1A -177(2) . . . . ?
O6A S1A C7A C6A -21(3) . . . . ?
O5A S1A C7A C6A -152(3) . . . . ?
N1A S1A C7A C6A 90(3) . . . . ?
O6A S1A C7A C8A 159(2) . . . . ?
O5A S1A C7A C8A 29(3) . . . . ?
N1A S1A C7A C8A -90(3) . . . . ?
C6A C7A C8A C9A -6(4) . . . . ?
S1A C7A C8A C9A 173.4(19) . . . . ?
C7A C8A C9A C4A 7(3) . . . . ?
C5A C4A C9A C8A -4(2) . . . . ?
C3A C4A C9A C8A 176.6(14) . . . . ?
S1A N1A C11A C10 85(3) . . . . ?
S1A N1A C11A C12A -140(2) . . . . ?
O4 C10 C11A N1A -149.3(16) . . . . ?
O3 C10 C11A N1A 31(2) . . . . ?
C11 C10 C11A N1A 34(6) . . . . ?
O4 C10 C11A C12A 86.2(19) . . . . ?
O3 C10 C11A C12A -93(2) . . . . ?
C11 C10 C11A C12A -90(6) . . . . ?
N1A C11A C12A C13A -62.4(18) . . . . ?
C10 C11A C12A C13A 64(2) . . . . ?
C11A C12A C13A S2 -178.0(9) . . . . ?
 
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 H20 O4  0.85(2) 1.79(2) 2.639(3) 174(5) 3_565
O3 H21 O2  0.82(2) 1.87(3) 2.643(4) 156(4) 3_565
N1 H22 S2  0.87(2) 2.43(5) 3.239(18) 154(8) 2_645
 
_refine_diff_density_max    0.508
_refine_diff_density_min   -0.290
_refine_diff_density_rms    0.061

_shelxl_version_number 2013-4



#==END

 
data_kaw45

# quasiracemate L3/D4 unreacted 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ?
_chemical_absolute_configuration  rm 
_chemical_formula_moiety          
  'C15 H19 N O6 S, C14 H17 N O6 S2'
_chemical_formula_sum 
 'C29 H36 N2 O12 S3' 
_chemical_formula_weight          700.78 
 
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' 
 
_space_group_crystal_system       triclinic
_space_group_IT_number            1
_space_group_name_H-M_alt         'P 1'
_space_group_name_Hall            'P 1'

 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 
_cell_length_a                    6.9045(2) 
_cell_length_b                    7.9441(2) 
_cell_length_c                    15.2565(4) 
_cell_angle_alpha                 82.911(1) 
_cell_angle_beta                  77.052(1) 
_cell_angle_gamma                 81.884(1) 
_cell_volume                      803.71(4) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9969 
_cell_measurement_theta_min       2.945
_cell_measurement_theta_max       71.808
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.41
_exptl_crystal_size_mid           0.31
_exptl_crystal_size_min           0.11
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.448 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              368 
_exptl_absorpt_coefficient_mu     2.679 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.419
_exptl_absorpt_correction_T_max   0.753
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11931
_diffrn_reflns_av_unetI/netI      0.0350
_diffrn_reflns_av_R_equivalents   0.0276
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.985
_diffrn_reflns_theta_max          68.222
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.957
_diffrn_measured_fraction_theta_full  0.958
_diffrn_reflns_Laue_measured_fraction_max    0.957
_diffrn_reflns_Laue_measured_fraction_full   0.958
_diffrn_reflns_point_group_measured_fraction_max   0.776
_diffrn_reflns_point_group_measured_fraction_full  0.779
_reflns_number_total              4571
_reflns_number_gt                 4522
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.622
_reflns_Friedel_fraction_max      0.595
_reflns_Friedel_fraction_full     0.601
 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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 a difference density map. The Non-H
 atoms were refined using anisotropic displacement parameter.  Each H atom
 was placed in calculated positions with Ueq = 1.2 x Uiso
 (1.5 x Uiso for methyl H atoms).  The remaining H atoms (O-H and N-H) were
 located in difference denisty maps and refined with Ueq = 1.2 x Uiso of the
 corresponding N/O atom and N/O-H distances restrained to 0.85(2) angstroms.
; 
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0620P)²+0.4775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1692 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.111(8)
_refine_ls_number_reflns          4571
_refine_ls_number_parameters      436
_refine_ls_number_restraints      9
_refine_ls_R_factor_all           0.0382
_refine_ls_R_factor_gt            0.0379
_refine_ls_wR_factor_ref          0.1037
_refine_ls_wR_factor_gt           0.1035
_refine_ls_goodness_of_fit_ref    1.073
_refine_ls_restrained_S_all       1.072
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.00075(14) 0.00004(10) 0.00001(6) 0.0204(2) Uani 1 1 d . . . . .
O1A O 0.0123(5) -0.9709(4) 0.3437(2) 0.0236(7) Uani 1 1 d D . . . .
H1 H 0.023(8) -1.063(5) 0.379(3) 0.028 Uiso 1 1 d D U . . .
O2A O 0.0750(5) -0.8563(3) 0.4598(2) 0.0222(7) Uani 1 1 d . . . . .
O3A O 0.3888(6) -0.4426(4) -0.1002(2) 0.0310(8) Uani 1 1 d D . . . .
H2 H 0.421(9) -0.529(5) -0.065(3) 0.037 Uiso 1 1 d D U . . .
O4A O 0.4412(5) -0.3223(4) 0.0165(2) 0.0274(8) Uani 1 1 d . . . . .
O5A O -0.1195(6) -0.0078(4) -0.0629(2) 0.0319(8) Uani 1 1 d . . . . .
O6A O -0.0287(6) 0.1457(4) 0.0504(2) 0.0325(8) Uani 1 1 d . . . . .
N1A N 0.2341(7) -0.0107(5) -0.0509(3) 0.0255(8) Uani 1 1 d D . . . .
H3 H 0.313(7) 0.048(6) -0.034(3) 0.031 Uiso 1 1 d D U . . .
C1A C 0.0393(7) -0.8398(5) 0.3831(3) 0.0176(9) Uani 1 1 d . . . . .
C2A C 0.0294(7) -0.6736(5) 0.3298(3) 0.0216(9) Uani 1 1 d . . . . .
H2A H 0.0484 -0.5772 0.3567 0.026 Uiso 1 1 calc R U . . .
C3A C -0.0045(7) -0.6477(5) 0.2462(3) 0.0207(10) Uani 1 1 d . . . . .
H3A H -0.0244 -0.7452 0.2205 0.025 Uiso 1 1 calc R U . . .
C4A C -0.0141(7) -0.4861(5) 0.1905(3) 0.0195(9) Uani 1 1 d . . . . .
C5A C -0.0623(7) -0.4820(5) 0.1059(3) 0.0215(9) Uani 1 1 d . . . . .
H5A H -0.0903 -0.5836 0.0867 0.026 Uiso 1 1 calc R U . . .
C6A C -0.0695(7) -0.3312(5) 0.0496(3) 0.0215(9) Uani 1 1 d . . . . .
H6A H -0.1059 -0.3285 -0.0070 0.026 Uiso 1 1 calc R U . . .
C7A C -0.0232(7) -0.1846(5) 0.0768(3) 0.0188(9) Uani 1 1 d . . . . .
C8A C 0.0210(7) -0.1838(5) 0.1624(3) 0.0196(9) Uani 1 1 d . . . . .
H8A H 0.0490 -0.0818 0.1812 0.024 Uiso 1 1 calc R U . . .
C9A C 0.0230(7) -0.3347(5) 0.2188(3) 0.0180(9) Uani 1 1 d . . . . .
H9A H 0.0497 -0.3354 0.2773 0.022 Uiso 1 1 calc R U . . .
C10A C 0.3905(7) -0.3117(5) -0.0555(3) 0.0239(10) Uani 1 1 d . . . . .
C11A C 0.3275(7) -0.1441(5) -0.1085(3) 0.0258(10) Uani 1 1 d . . . . .
H11A H 0.2318 -0.1656 -0.1452 0.031 Uiso 1 1 calc R U . . .
C12A C 0.5160(8) -0.0883(6) -0.1719(3) 0.0243(10) Uani 1 1 d . . . . .
H12A H 0.5837 -0.1850 -0.2068 0.029 Uiso 1 1 calc R U . . .
H12B H 0.6077 -0.0634 -0.1350 0.029 Uiso 1 1 calc R U . . .
C13A C 0.4831(8) 0.0692(6) -0.2391(3) 0.0341(11) Uani 1 1 d . . . . .
H13A H 0.4136 0.1678 -0.2048 0.041 Uiso 1 1 calc R U . . .
C14A C 0.3576(10) 0.0346(8) -0.3036(4) 0.0526(15) Uani 1 1 d . . . . .
H14A H 0.4254 -0.0619 -0.3374 0.079 Uiso 1 1 calc R U . . .
H14B H 0.3403 0.1362 -0.3459 0.079 Uiso 1 1 calc R U . . .
H14C H 0.2263 0.0071 -0.2692 0.079 Uiso 1 1 calc R U . . .
C15A C 0.6900(8) 0.1156(6) -0.2958(4) 0.0390(12) Uani 1 1 d . . . . .
H15A H 0.7814 0.1176 -0.2553 0.059 Uiso 1 1 calc R U . . .
H15B H 0.6722 0.2283 -0.3292 0.059 Uiso 1 1 calc R U . . .
H15C H 0.7463 0.0299 -0.3385 0.059 Uiso 1 1 calc R U . . .
S1B S 0.51129(14) -1.58669(10) 0.46046(7) 0.0223(2) Uani 1 1 d . . . . .
S2B S 0.0061(2) -1.39895(13) 0.78531(8) 0.0341(3) Uani 1 1 d . . . . .
O1B O 0.4955(5) -0.6234(4) 0.1154(2) 0.0251(7) Uani 1 1 d D . . . .
H4 H 0.482(9) -0.540(5) 0.077(3) 0.030 Uiso 1 1 d D U . . .
O2B O 0.4445(5) -0.7383(4) -0.0036(2) 0.0280(7) Uani 1 1 d . . . . .
O3B O 0.1351(6) -1.1532(4) 0.5574(2) 0.0274(7) Uani 1 1 d D . . . .
H5 H 0.122(8) -1.054(4) 0.528(3) 0.033 Uiso 1 1 d D U . . .
O4B O 0.0593(5) -1.2720(4) 0.4456(2) 0.0223(6) Uani 1 1 d . . . . .
O5B O 0.6193(5) -1.5651(4) 0.5274(2) 0.0316(8) Uani 1 1 d . . . . .
O6B O 0.5602(5) -1.7358(4) 0.4120(2) 0.0312(8) Uani 1 1 d . . . . .
N1B N 0.2777(6) -1.5826(4) 0.5075(2) 0.0218(8) Uani 1 1 d D . . . .
H6 H 0.213(7) -1.646(6) 0.487(3) 0.026 Uiso 1 1 d D U . . .
C1B C 0.4750(7) -0.7542(6) 0.0733(3) 0.0234(10) Uani 1 1 d . . . . .
C2B C 0.4871(7) -0.9211(5) 0.1258(3) 0.0213(9) Uani 1 1 d . . . . .
H2B H 0.4744 -1.0188 0.0983 0.026 Uiso 1 1 calc R U . . .
C3B C 0.5149(7) -0.9424(5) 0.2100(3) 0.0223(10) Uani 1 1 d . . . . .
H3B H 0.5299 -0.8431 0.2356 0.027 Uiso 1 1 calc R U . . .
C4B C 0.5246(7) -1.1052(5) 0.2675(3) 0.0192(9) Uani 1 1 d . . . . .
C5B C 0.5657(7) -1.1060(5) 0.3529(3) 0.0232(9) Uani 1 1 d . . . . .
H5B H 0.5914 -1.0032 0.3717 0.028 Uiso 1 1 calc R U . . .
C6B C 0.5696(7) -1.2542(5) 0.4104(3) 0.0214(9) Uani 1 1 d . . . . .
H6B H 0.5989 -1.2545 0.4684 0.026 Uiso 1 1 calc R U . . .
C7B C 0.5299(7) -1.4036(5) 0.3820(3) 0.0201(9) Uani 1 1 d . . . . .
C8B C 0.4929(8) -1.4060(6) 0.2972(3) 0.0220(9) Uani 1 1 d . . . . .
H8B H 0.4697 -1.5099 0.2785 0.026 Uiso 1 1 calc R U . . .
C9B C 0.4893(7) -1.2596(5) 0.2396(3) 0.0220(9) Uani 1 1 d . . . . .
H9B H 0.4633 -1.2615 0.1812 0.026 Uiso 1 1 calc R U . . .
C10B C 0.1162(7) -1.2851(5) 0.5165(3) 0.0191(9) Uani 1 1 d . . . . .
C11B C 0.1746(7) -1.4562(5) 0.5676(3) 0.0195(9) Uani 1 1 d . . . . .
H11B H 0.2633 -1.4381 0.6084 0.023 Uiso 1 1 calc R U . . .
C12B C -0.0153(7) -1.5273(5) 0.6251(3) 0.0224(9) Uani 1 1 d . . . . .
H12C H -0.1054 -1.5400 0.5848 0.027 Uiso 1 1 calc R U . . .
H12D H 0.0233 -1.6424 0.6536 0.027 Uiso 1 1 calc R U . . .
C13B C -0.1294(7) -1.4163(5) 0.6987(3) 0.0283(10) Uani 1 1 d . . . . .
H13C H -0.2559 -1.4638 0.7276 0.034 Uiso 1 1 calc R U . . .
H13B H -0.1645 -1.3003 0.6703 0.034 Uiso 1 1 calc R U . . .
C14B C -0.0200(8) -1.6045(6) 0.8478(3) 0.0351(11) Uani 1 1 d . . . . .
H14D H -0.1620 -1.6141 0.8731 0.053 Uiso 1 1 calc R U . . .
H14E H 0.0528 -1.6171 0.8968 0.053 Uiso 1 1 calc R U . . .
H14F H 0.0348 -1.6943 0.8074 0.053 Uiso 1 1 calc R U . . .
 
 
_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 O5A 1.414(4) . ?
S1 O6A 1.433(3) . ?
S1 N1A 1.619(4) . ?
S1 C7A 1.763(4) . ?
O1A C1A 1.319(5) . ?
O1A H1 0.86(2) . ?
O2A C1A 1.238(5) . ?
O3A C10A 1.315(6) . ?
O3A H2 0.85(3) . ?
O4A C10A 1.216(6) . ?
N1A C11A 1.448(6) . ?
N1A H3 0.86(3) . ?
C1A C2A 1.464(5) . ?
C2A C3A 1.334(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.452(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.400(6) . ?
C4A C9A 1.401(6) . ?
C5A C6A 1.386(6) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.383(6) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.407(6) . ?
C8A C9A 1.387(6) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.530(6) . ?
C11A C12A 1.524(7) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.541(6) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.520(8) . ?
C13A C15A 1.563(7) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
S1B O5B 1.431(4) . ?
S1B O6B 1.433(3) . ?
S1B N1B 1.609(4) . ?
S1B C7B 1.766(4) . ?
S2B C14B 1.797(5) . ?
S2B C13B 1.810(5) . ?
O1B C1B 1.326(6) . ?
O1B H4 0.84(3) . ?
O2B C1B 1.227(6) . ?
O3B C10B 1.319(5) . ?
O3B H5 0.87(3) . ?
O4B C10B 1.219(5) . ?
N1B C11B 1.445(5) . ?
N1B H6 0.84(3) . ?
C1B C2B 1.463(6) . ?
C2B C3B 1.328(6) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.473(6) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.392(6) . ?
C4B C9B 1.416(6) . ?
C5B C6B 1.381(6) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.394(6) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.377(6) . ?
C8B C9B 1.370(6) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.532(5) . ?
C11B C12B 1.543(6) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.520(6) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13C 0.9900 . ?
C13B H13B 0.9900 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 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
O5A S1 O6A 120.1(2) . . ?
O5A S1 N1A 109.9(2) . . ?
O6A S1 N1A 104.0(2) . . ?
O5A S1 C7A 107.3(2) . . ?
O6A S1 C7A 108.48(19) . . ?
N1A S1 C7A 106.3(2) . . ?
C1A O1A H1 110(4) . . ?
C10A O3A H2 103(4) . . ?
C11A N1A S1 122.0(4) . . ?
C11A N1A H3 117(4) . . ?
S1 N1A H3 120(4) . . ?
O2A C1A O1A 122.2(4) . . ?
O2A C1A C2A 121.7(4) . . ?
O1A C1A C2A 116.1(4) . . ?
C3A C2A C1A 124.7(4) . . ?
C3A C2A H2A 117.7 . . ?
C1A C2A H2A 117.7 . . ?
C2A C3A C4A 126.7(4) . . ?
C2A C3A H3A 116.6 . . ?
C4A C3A H3A 116.6 . . ?
C5A C4A C9A 119.1(4) . . ?
C5A C4A C3A 118.7(4) . . ?
C9A C4A C3A 122.2(4) . . ?
C6A C5A C4A 120.7(4) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C7A C6A C5A 119.4(4) . . ?
C7A C6A H6A 120.3 . . ?
C5A C6A H6A 120.3 . . ?
C6A C7A C8A 121.2(4) . . ?
C6A C7A S1 119.7(3) . . ?
C8A C7A S1 119.0(3) . . ?
C9A C8A C7A 118.7(4) . . ?
C9A C8A H8A 120.6 . . ?
C7A C8A H8A 120.6 . . ?
C8A C9A C4A 120.8(4) . . ?
C8A C9A H9A 119.6 . . ?
C4A C9A H9A 119.6 . . ?
O4A C10A O3A 124.6(4) . . ?
O4A C10A C11A 124.9(4) . . ?
O3A C10A C11A 110.5(4) . . ?
N1A C11A C12A 109.8(4) . . ?
N1A C11A C10A 113.0(4) . . ?
C12A C11A C10A 106.9(4) . . ?
N1A C11A H11A 109.0 . . ?
C12A C11A H11A 109.0 . . ?
C10A C11A H11A 109.0 . . ?
C11A C12A C13A 115.5(4) . . ?
C11A C12A H12A 108.4 . . ?
C13A C12A H12A 108.4 . . ?
C11A C12A H12B 108.4 . . ?
C13A C12A H12B 108.4 . . ?
H12A C12A H12B 107.5 . . ?
C14A C13A C12A 111.3(4) . . ?
C14A C13A C15A 108.4(4) . . ?
C12A C13A C15A 109.4(4) . . ?
C14A C13A H13A 109.3 . . ?
C12A C13A H13A 109.3 . . ?
C15A C13A H13A 109.3 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O5B S1B O6B 120.2(2) . . ?
O5B S1B N1B 108.5(2) . . ?
O6B S1B N1B 105.83(19) . . ?
O5B S1B C7B 106.9(2) . . ?
O6B S1B C7B 108.8(2) . . ?
N1B S1B C7B 105.8(2) . . ?
C14B S2B C13B 99.6(2) . . ?
C1B O1B H4 102(4) . . ?
C10B O3B H5 117(4) . . ?
C11B N1B S1B 122.6(3) . . ?
C11B N1B H6 121(4) . . ?
S1B N1B H6 116(4) . . ?
O2B C1B O1B 123.1(4) . . ?
O2B C1B C2B 121.5(4) . . ?
O1B C1B C2B 115.4(4) . . ?
C3B C2B C1B 123.1(4) . . ?
C3B C2B H2B 118.4 . . ?
C1B C2B H2B 118.4 . . ?
C2B C3B C4B 126.3(4) . . ?
C2B C3B H3B 116.9 . . ?
C4B C3B H3B 116.9 . . ?
C5B C4B C9B 119.2(4) . . ?
C5B C4B C3B 118.7(4) . . ?
C9B C4B C3B 122.1(4) . . ?
C6B C5B C4B 120.8(4) . . ?
C6B C5B H5B 119.6 . . ?
C4B C5B H5B 119.6 . . ?
C5B C6B C7B 118.8(4) . . ?
C5B C6B H6B 120.6 . . ?
C7B C6B H6B 120.6 . . ?
C8B C7B C6B 121.1(4) . . ?
C8B C7B S1B 120.6(3) . . ?
C6B C7B S1B 118.1(3) . . ?
C9B C8B C7B 120.4(4) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C8B C9B C4B 119.7(4) . . ?
C8B C9B H9B 120.2 . . ?
C4B C9B H9B 120.2 . . ?
O4B C10B O3B 123.8(4) . . ?
O4B C10B C11B 123.7(4) . . ?
O3B C10B C11B 112.5(3) . . ?
N1B C11B C10B 112.3(3) . . ?
N1B C11B C12B 107.7(3) . . ?
C10B C11B C12B 109.6(4) . . ?
N1B C11B H11B 109.1 . . ?
C10B C11B H11B 109.1 . . ?
C12B C11B H11B 109.1 . . ?
C13B C12B C11B 114.0(4) . . ?
C13B C12B H12C 108.8 . . ?
C11B C12B H12C 108.8 . . ?
C13B C12B H12D 108.8 . . ?
C11B C12B H12D 108.8 . . ?
H12C C12B H12D 107.7 . . ?
C12B C13B S2B 114.3(3) . . ?
C12B C13B H13C 108.7 . . ?
S2B C13B H13C 108.7 . . ?
C12B C13B H13B 108.7 . . ?
S2B C13B H13B 108.7 . . ?
H13C C13B H13B 107.6 . . ?
S2B C14B H14D 109.5 . . ?
S2B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
S2B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 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
O5A S1 N1A C11A -51.4(4) . . . . ?
O6A S1 N1A C11A 178.8(3) . . . . ?
C7A S1 N1A C11A 64.4(4) . . . . ?
O2A C1A C2A C3A 178.6(4) . . . . ?
O1A C1A C2A C3A 0.0(7) . . . . ?
C1A C2A C3A C4A -179.5(4) . . . . ?
C2A C3A C4A C5A -176.5(4) . . . . ?
C2A C3A C4A C9A 3.4(8) . . . . ?
C9A C4A C5A C6A 1.3(7) . . . . ?
C3A C4A C5A C6A -178.8(4) . . . . ?
C4A C5A C6A C7A 1.8(7) . . . . ?
C5A C6A C7A C8A -3.3(7) . . . . ?
C5A C6A C7A S1 171.6(3) . . . . ?
O5A S1 C7A C6A 26.8(4) . . . . ?
O6A S1 C7A C6A 157.9(4) . . . . ?
N1A S1 C7A C6A -90.7(4) . . . . ?
O5A S1 C7A C8A -158.2(4) . . . . ?
O6A S1 C7A C8A -27.1(4) . . . . ?
N1A S1 C7A C8A 84.3(4) . . . . ?
C6A C7A C8A C9A 1.8(7) . . . . ?
S1 C7A C8A C9A -173.1(3) . . . . ?
C7A C8A C9A C4A 1.4(7) . . . . ?
C5A C4A C9A C8A -2.9(7) . . . . ?
C3A C4A C9A C8A 177.2(4) . . . . ?
S1 N1A C11A C12A 159.6(3) . . . . ?
S1 N1A C11A C10A -81.1(5) . . . . ?
O4A C10A C11A N1A -30.3(7) . . . . ?
O3A C10A C11A N1A 151.8(4) . . . . ?
O4A C10A C11A C12A 90.7(5) . . . . ?
O3A C10A C11A C12A -87.2(5) . . . . ?
N1A C11A C12A C13A -63.1(5) . . . . ?
C10A C11A C12A C13A 173.9(4) . . . . ?
C11A C12A C13A C14A -63.0(6) . . . . ?
C11A C12A C13A C15A 177.2(4) . . . . ?
O5B S1B N1B C11B 45.6(4) . . . . ?
O6B S1B N1B C11B 175.9(3) . . . . ?
C7B S1B N1B C11B -68.8(4) . . . . ?
O2B C1B C2B C3B -178.2(5) . . . . ?
O1B C1B C2B C3B 0.5(7) . . . . ?
C1B C2B C3B C4B 178.7(4) . . . . ?
C2B C3B C4B C5B 176.5(4) . . . . ?
C2B C3B C4B C9B -4.8(8) . . . . ?
C9B C4B C5B C6B -0.9(7) . . . . ?
C3B C4B C5B C6B 177.8(4) . . . . ?
C4B C5B C6B C7B -0.5(7) . . . . ?
C5B C6B C7B C8B 1.9(7) . . . . ?
C5B C6B C7B S1B -173.9(3) . . . . ?
O5B S1B C7B C8B 161.2(4) . . . . ?
O6B S1B C7B C8B 29.9(4) . . . . ?
N1B S1B C7B C8B -83.4(4) . . . . ?
O5B S1B C7B C6B -23.0(4) . . . . ?
O6B S1B C7B C6B -154.3(4) . . . . ?
N1B S1B C7B C6B 92.4(4) . . . . ?
C6B C7B C8B C9B -1.7(7) . . . . ?
S1B C7B C8B C9B 173.9(4) . . . . ?
C7B C8B C9B C4B 0.2(7) . . . . ?
C5B C4B C9B C8B 1.1(7) . . . . ?
C3B C4B C9B C8B -177.6(4) . . . . ?
S1B N1B C11B C10B 79.6(4) . . . . ?
S1B N1B C11B C12B -159.7(3) . . . . ?
O4B C10B C11B N1B 37.4(6) . . . . ?
O3B C10B C11B N1B -142.4(4) . . . . ?
O4B C10B C11B C12B -82.3(5) . . . . ?
O3B C10B C11B C12B 97.9(4) . . . . ?
N1B C11B C12B C13B 174.1(3) . . . . ?
C10B C11B C12B C13B -63.4(5) . . . . ?
C11B C12B C13B S2B -64.7(4) . . . . ?
C14B S2B C13B C12B -76.0(4) . . . . ?
 
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 H1 O4B  0.86(2) 1.85(3) 2.708(4) 175(5) .
O3B H5 O2A  0.87(3) 1.80(3) 2.663(4) 173(6) .
O3A H2 O2B  0.85(3) 1.81(3) 2.643(4) 164(6) .
O1B H4 O4A  0.84(3) 1.87(3) 2.692(4) 165(5) .
N1A H3 O2B  0.86(3) 2.18(3) 3.009(5) 162(5) 1_565
N1B H6 O2A  0.84(3) 2.16(3) 2.987(5) 166(5) 1_545
 
_refine_diff_density_max    0.514
_refine_diff_density_min   -0.310
_refine_diff_density_rms    0.063

_shelxl_version_number 2013-4



#==END

 
data_kaw111
# quasiracmeate UV irradiated 4 hrs
 
# start Validation Reply Form
_vrf_PLAT089_kaw111
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.50       
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT213_kaw111
;
PROBLEM: Atom O5A             has ADP max/min Ratio .....        4.8 oblate
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT220_kaw111
;
PROBLEM: Large Non-Solvent    O     Ueq(max)/Ueq(min) ...        4.1 Ratio 
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT340_kaw111
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0179 Ang.  
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
# end Validation Reply Form




_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C29 H36 N2 O12 S3'
_chemical_formula_sum
 'C29 H36 N2 O12 S3' 
_chemical_formula_weight          700.78

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            1
_space_group_name_H-M_alt         'P 1'
_space_group_name_Hall            'P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 
_cell_length_a                    6.8872(3)
_cell_length_b                    7.9769(4)
_cell_length_c                    15.0753(7)
_cell_angle_alpha                 93.167(3)
_cell_angle_beta                  102.378(3)
_cell_angle_gamma                 98.319(3)
_cell_volume                      797.26(7)
_cell_formula_units_Z             1
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     8131 
_cell_measurement_theta_min       3.013
_cell_measurement_theta_max       66.351
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.36
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.460          
_exptl_crystal_F_000              368
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_absorpt_coefficient_mu     2.701
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.297
_exptl_absorpt_correction_T_max   0.763 
_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  8.33
_diffrn_reflns_number             14944
_diffrn_reflns_av_unetI/netI      0.0570
_diffrn_reflns_av_R_equivalents   0.0454
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.013
_diffrn_reflns_theta_max          67.130
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.968
_diffrn_measured_fraction_theta_full  0.955
_diffrn_reflns_Laue_measured_fraction_max    0.968
_diffrn_reflns_Laue_measured_fraction_full   0.955
_diffrn_reflns_point_group_measured_fraction_max   0.829
_diffrn_reflns_point_group_measured_fraction_full  0.818
_reflns_number_total              4722
_reflns_number_gt                 4394
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.712
_reflns_Friedel_fraction_max      0.689
_reflns_Friedel_fraction_full     0.680
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

Crystal irradiated using a 200W Xe(Hg) lamp for 240, 660, and 1320 min to
 give a crystal with noticable fractures. This sample represents
 240 min and 26% conversion.  Data collection was carried out
 at room temperature to minimize/exclude thermal shock that
 can result in sample degredation.  The diffraction pattern showed the
 expected signs of crystal twinning. Because the dominant twin component
 was considerably stronger and well dispersed from the minor component
 reflections, data were harvested as untwinned data.   

All non-hydrogen atoms were located in a series of difference density maps.
 Reaction progress was determined by the refinement of occupancy factors
 of the reactant and photodimer components.  Non-H atoms associated with 
 the major component (reactant) were refined using anisotropic
 displacement parameters while the minor component (photodimer) was refined
 using isotropic parameters. Each C-H hydrogen atom was placed in 
 calculated positions with Ueq = 1.2 x Uiso (1.5 x Uiso for methyl H
 atoms).  The remaining H atoms (O-H and N-H) were located in difference
 denisty maps and refined with Ueq = 1.2 x Uiso of the
 corresponding N/O atom and N/O-H distances restrained to 0.85(2) angstroms.

Addiional constraints to the structural model include:
FLAT - four phenyl and four carboxylic acid groups
RIGU - two reactant phenyl groups
SADI - cyclobutane C atoms and carboxylic acid groups
;
 
_computing_data_collection        'APEX2'
_computing_cell_refinement        'APEX2'
_computing_data_reduction         
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material   'XSEED (Barbour, 2001)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1287P)²+1.4659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.169(16)
_chemical_absolute_configuration  rm
_refine_ls_number_reflns          4722
_refine_ls_number_parameters      518
_refine_ls_number_restraints      131
_refine_ls_R_factor_all           0.0890
_refine_ls_R_factor_gt            0.0840
_refine_ls_wR_factor_ref          0.2389
_refine_ls_wR_factor_gt           0.2339
_refine_ls_goodness_of_fit_ref    1.122
_refine_ls_restrained_S_all       1.110
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1A S 0.1326(5) 0.6708(3) 0.9790(2) 0.0282(10) Uani 0.742(10) 1 d . . P A 1
O1A O -0.4058(11) -0.1750(9) 0.5201(5) 0.0473(19) Uani 1 1 d D . . . .
O2A O -0.2256(11) -0.2973(10) 0.6330(5) 0.0460(18) Uani 1 1 d D . . . .
O3A O -0.3204(14) 0.3645(13) 0.9677(6) 0.066(3) Uani 1 1 d . . . . .
O4A O -0.1583(14) 0.2357(11) 1.0830(6) 0.057(2) Uani 1 1 d D . . . .
O5A O 0.1158(16) 0.8142(10) 0.9278(7) 0.037(2) Uani 0.742(10) 1 d . . P A 1
O6A O 0.3167(15) 0.6599(12) 1.0425(8) 0.038(2) Uani 0.742(10) 1 d . . P A 1
N1A N -0.0454(14) 0.6677(11) 1.0325(6) 0.047(2) Uani 1 1 d D . . . .
H22A H -0.1197 0.7460 1.0255 0.056 Uiso 1 1 calc DR U . A 1
C1A C -0.2969(16) -0.1695(16) 0.5983(7) 0.047(3) Uani 1 1 d . . . . .
C2A C -0.229(2) 0.002(2) 0.6482(9) 0.044(4) Uani 0.742(10) 1 d . . P A 1
H2A H -0.2684 0.0956 0.6194 0.053 Uiso 0.742(10) 1 calc R U P A 1
C3A C -0.1089(18) 0.0287(16) 0.7359(8) 0.029(3) Uani 0.742(10) 1 d . . P A 1
H3A H -0.0681 -0.0671 0.7619 0.035 Uiso 0.742(10) 1 calc R U P A 1
C4A C -0.041(2) 0.1872(18) 0.7912(8) 0.029(3) Uani 0.742(10) 1 d D U P A 1
C5A C -0.1042(19) 0.3381(16) 0.7610(8) 0.028(3) Uani 0.742(10) 1 d D U P A 1
H5A H -0.1861 0.3370 0.7032 0.033 Uiso 0.742(10) 1 calc R U P A 1
C6A C -0.047(3) 0.484(2) 0.8155(10) 0.038(4) Uani 0.742(10) 1 d D U P A 1
H6A H -0.0890 0.5836 0.7953 0.045 Uiso 0.742(10) 1 calc R U P A 1
C7A C 0.077(2) 0.4853(15) 0.9041(9) 0.028(3) Uani 0.742(10) 1 d D U P A 1
C8A C 0.148(2) 0.3411(18) 0.9326(10) 0.029(4) Uani 0.742(10) 1 d D U P A 1
H8A H 0.2365 0.3436 0.9888 0.035 Uiso 0.742(10) 1 calc R U P A 1
C9A C 0.084(2) 0.191(2) 0.8764(9) 0.032(4) Uani 0.742(10) 1 d D U P A 1
H9A H 0.1258 0.0915 0.8966 0.038 Uiso 0.742(10) 1 calc R U P A 1
C10A C -0.2002(16) 0.3684(15) 1.0402(8) 0.045(2) Uani 1 1 d . . . . .
C11A C -0.0851(18) 0.5368(15) 1.0924(7) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.0444 0.5153 1.1278 0.055 Uiso 1 1 calc R U . . .
C12A C -0.2039(18) 0.5952(14) 1.1582(10) 0.054(3) Uani 1 1 d . . . . .
H12A H -0.2386 0.5008 1.1927 0.064 Uiso 1 1 calc R U . . .
H12B H -0.3289 0.6227 1.1231 0.064 Uiso 1 1 calc R U . . .
C13A C -0.101(2) 0.7468(19) 1.2248(10) 0.068(3) Uani 1 1 d . . . . .
H13A H -0.0612 0.8418 1.1905 0.082 Uiso 1 1 calc R U . . .
C14A C -0.252(2) 0.7985(19) 1.2795(11) 0.075(4) Uani 1 1 d . . . . .
H14A H -0.2918 0.7063 1.3134 0.112 Uiso 1 1 calc R U . . .
H14B H -0.3685 0.8244 1.2383 0.112 Uiso 1 1 calc R U . . .
H14C H -0.1895 0.8968 1.3208 0.112 Uiso 1 1 calc R U . . .
C15A C 0.085(3) 0.706(2) 1.2884(11) 0.100(6) Uani 1 1 d . . . . .
H15A H 0.0461 0.6219 1.3271 0.150 Uiso 1 1 calc R U . . .
H15B H 0.1564 0.8075 1.3252 0.150 Uiso 1 1 calc R U . . .
H15C H 0.1709 0.6630 1.2531 0.150 Uiso 1 1 calc R U . . .
H20A H -0.259(12) -0.389(4) 0.598(3) 0.120 Uiso 1 1 d D U . . .
H21A H -0.223(17) 0.151(17) 1.046(10) 0.120 Uiso 1 1 d D U . . .
S1B S -0.8407(8) -0.8956(7) 0.5206(4) 0.0514(13) Uani 0.742(10) 1 d . . P A 1
S2B S -0.6521(5) -0.7257(4) 0.1928(2) 0.0615(9) Uani 1 1 d . . . . .
O1B O -0.2968(12) -0.0564(10) 0.9837(5) 0.0493(19) Uani 1 1 d . . . . .
O2B O -0.4743(12) 0.0631(10) 0.8708(5) 0.051(2) Uani 1 1 d D . . . .
O3B O -0.3696(11) -0.5969(9) 0.5349(5) 0.0431(17) Uani 1 1 d D . . . .
O4B O -0.5465(14) -0.4713(10) 0.4226(5) 0.056(2) Uani 1 1 d D . . . .
O5B O -0.866(3) -1.0415(19) 0.5695(12) 0.084(5) Uani 0.742(10) 1 d . . P A 1
O6B O -1.009(2) -0.8651(18) 0.4528(10) 0.058(4) Uani 0.742(10) 1 d . . P A 1
N1B N -0.6711(17) -0.8944(13) 0.4756(7) 0.062(3) Uani 1 1 d D . . . .
H22B H -0.5983 -0.9727 0.4879 0.074 Uiso 1 1 calc DR U . A 1
C1B C -0.4042(18) -0.0671(17) 0.9090(8) 0.052(3) Uani 1 1 d . . . . .
C2B C -0.476(2) -0.2383(17) 0.8534(10) 0.041(3) Uani 0.742(10) 1 d . . P A 1
H2B H -0.4398 -0.3351 0.8797 0.050 Uiso 0.742(10) 1 calc R U P A 1
C3B C -0.584(2) -0.255(2) 0.7725(11) 0.053(4) Uani 0.742(10) 1 d . . P A 1
H3B H -0.6185 -0.1572 0.7470 0.063 Uiso 0.742(10) 1 calc R U P A 1
C4B C -0.6585(19) -0.418(2) 0.7159(10) 0.043(3) Uani 0.742(10) 1 d D U P A 1
C5B C -0.601(2) -0.577(2) 0.7408(10) 0.050(4) Uani 0.742(10) 1 d D U P A 1
H5B H -0.5171 -0.5814 0.7975 0.060 Uiso 0.742(10) 1 calc R U P A 1
C6B C -0.668(2) -0.725(3) 0.6821(10) 0.051(4) Uani 0.742(10) 1 d D U P A 1
H6B H -0.6333 -0.8288 0.6987 0.061 Uiso 0.742(10) 1 calc R U P A 1
C7B C -0.786(3) -0.710(3) 0.5999(10) 0.042(4) Uani 0.742(10) 1 d D U P A 1
C8B C -0.848(2) -0.558(2) 0.5703(11) 0.041(3) Uani 0.742(10) 1 d D U P A 1
H8B H -0.9299 -0.5561 0.5127 0.050 Uiso 0.742(10) 1 calc R U P A 1
C9B C -0.7865(19) -0.415(2) 0.6279(10) 0.041(3) Uani 0.742(10) 1 d D U P A 1
H9B H -0.8275 -0.3133 0.6102 0.049 Uiso 0.742(10) 1 calc R U P A 1
C10B C -0.4941(18) -0.6046(14) 0.4615(6) 0.047(3) Uani 1 1 d . . . . .
C11B C -0.6140(17) -0.7784(14) 0.4141(7) 0.048(3) Uani 1 1 d . . . . .
H11B H -0.7371 -0.7564 0.3732 0.058 Uiso 1 1 calc R U . . .
C12B C -0.4824(18) -0.8558(15) 0.3542(7) 0.048(3) Uani 1 1 d . . . . .
H12C H -0.3569 -0.8724 0.3936 0.058 Uiso 1 1 calc R U . . .
H12D H -0.5528 -0.9666 0.3263 0.058 Uiso 1 1 calc R U . . .
C13B C -0.4349(18) -0.7477(18) 0.2800(8) 0.061(3) Uani 1 1 d . . . . .
H13B H -0.3403 -0.7973 0.2516 0.073 Uiso 1 1 calc R U . . .
H13C H -0.3694 -0.6353 0.3077 0.073 Uiso 1 1 calc R U . . .
C14B C -0.6946(18) -0.9304(17) 0.1304(8) 0.057(3) Uani 1 1 d . . . . .
H14D H -0.5843 -0.9406 0.1019 0.085 Uiso 1 1 calc R U . . .
H14E H -0.8174 -0.9427 0.0845 0.085 Uiso 1 1 calc R U . . .
H14F H -0.7048 -1.0176 0.1714 0.085 Uiso 1 1 calc R U . . .
H20B H -0.436(16) 0.153(11) 0.908(7) 0.068 Uiso 1 1 d D U . . .
H21B H -0.487(10) -0.378(3) 0.451(4) 0.068 Uiso 1 1 d D U . . .
S1C S 0.194(5) 0.654(4) 0.947(2) 0.125(10) Uiso 0.258(10) 1 d . . P A 2
O5C O 0.192(12) 0.812(11) 0.899(6) 0.15(3) Uiso 0.258(10) 1 d . . P A 2
O6C O 0.372(10) 0.670(10) 1.019(5) 0.11(2) Uiso 0.258(10) 1 d . . P A 2
C2C C -0.367(4) -0.069(4) 0.679(2) 0.031(8) Uiso 0.258(10) 1 d D . P A 2
H2C H -0.4078 0.0386 0.6604 0.037 Uiso 0.258(10) 1 calc R U P A 2
C3C C -0.201(5) -0.039(4) 0.771(2) 0.038(9) Uiso 0.258(10) 1 d D . P A 2
H3C H -0.0959 -0.1072 0.7650 0.045 Uiso 0.258(10) 1 calc R U P A 2
C4C C -0.103(7) 0.140(5) 0.801(3) 0.048(14) Uiso 0.258(10) 1 d D . P A 2
C5C C -0.170(7) 0.293(6) 0.777(3) 0.060(16) Uiso 0.258(10) 1 d D . P A 2
H5C H -0.2841 0.2865 0.7297 0.072 Uiso 0.258(10) 1 calc R U P A 2
C6C C -0.080(9) 0.447(6) 0.817(4) 0.07(3) Uiso 0.258(10) 1 d D . P A 2
H6C H -0.1303 0.5442 0.7980 0.088 Uiso 0.258(10) 1 calc R U P A 2
C7C C 0.096(10) 0.459(8) 0.889(5) 0.088 Uiso 0.258(10) 1 d D U P A 2
C8C C 0.164(8) 0.314(9) 0.916(4) 0.06(2) Uiso 0.258(10) 1 d D . P A 2
H8C H 0.2788 0.3199 0.9624 0.074 Uiso 0.258(10) 1 calc R U P A 2
C9C C 0.064(10) 0.158(8) 0.874(5) 0.11(5) Uiso 0.258(10) 1 d D . P A 2
H9C H 0.1100 0.0606 0.8945 0.135 Uiso 0.258(10) 1 calc R U P A 2
S1D S -0.880(4) -0.865(4) 0.5348(18) 0.076(8) Uiso 0.258(10) 1 d . . P A 2
O5D O -0.789(9) -1.010(8) 0.597(4) 0.09(2) Uiso 0.258(10) 1 d . . P A 2
O6D O -1.049(11) -0.848(10) 0.481(5) 0.11(2) Uiso 0.258(10) 1 d . . P A 2
C2D C -0.352(5) -0.143(5) 0.821(3) 0.053(11) Uiso 0.258(10) 1 d D . P A 2
H2D H -0.3085 -0.2529 0.8325 0.064 Uiso 0.258(10) 1 calc R U P A 2
C3D C -0.521(6) -0.168(5) 0.731(2) 0.050(11) Uiso 0.258(10) 1 d D . P A 2
H3D H -0.6286 -0.1023 0.7362 0.060 Uiso 0.258(10) 1 calc R U P A 2
C4D C -0.606(5) -0.346(4) 0.692(2) 0.037(9) Uiso 0.258(10) 1 d D . P A 2
C5D C -0.553(6) -0.496(5) 0.731(2) 0.051(12) Uiso 0.258(10) 1 d D . P A 2
H5D H -0.4684 -0.4880 0.7882 0.061 Uiso 0.258(10) 1 calc R U P A 2
C6D C -0.629(7) -0.653(6) 0.683(3) 0.058(16) Uiso 0.258(10) 1 d D . P A 2
H6D H -0.5944 -0.7521 0.7075 0.070 Uiso 0.258(10) 1 calc R U P A 2
C7D C -0.755(10) -0.662(6) 0.600(4) 0.08(3) Uiso 0.258(10) 1 d D . P A 2
C8D C -0.809(8) -0.519(5) 0.555(3) 0.054(18) Uiso 0.258(10) 1 d D . P A 2
H8D H -0.8826 -0.5285 0.4953 0.064 Uiso 0.258(10) 1 calc R U P A 2
C9D C -0.747(6) -0.366(5) 0.605(2) 0.045(12) Uiso 0.258(10) 1 d D . P A 2
H9D H -0.7973 -0.2713 0.5819 0.054 Uiso 0.258(10) 1 calc R U P A 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1A O5A 1.420(8) . ?
S1A O6A 1.432(11) . ?
S1A N1A 1.604(11) . ?
S1A C7A 1.754(12) . ?
O1A C1A 1.249(13) . ?
O2A C1A 1.283(14) . ?
O2A H20A 0.85(3) . ?
O3A C10A 1.217(14) . ?
O4A C10A 1.305(14) . ?
O4A H21A 0.85(3) . ?
N1A C11A 1.451(14) . ?
N1A H22A 0.8600 . ?
C1A C2A 1.49(2) . ?
C1A C2C 1.62(3) . ?
C2A C3A 1.388(18) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.434(18) . ?
C3A H3A 0.9300 . ?
C4A C9A 1.380(15) . ?
C4A C5A 1.405(16) . ?
C5A C6A 1.34(2) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.422(16) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.367(16) . ?
C8A C9A 1.38(2) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.536(17) . ?
C11A C12A 1.509(17) . ?
C11A H11A 0.9800 . ?
C12A C13A 1.512(19) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C15A 1.52(2) . ?
C13A C14A 1.543(19) . ?
C13A H13A 0.9800 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
S1B O5B 1.422(15) . ?
S1B O6B 1.433(15) . ?
S1B N1B 1.470(14) . ?
S1B C7B 1.795(19) . ?
S2B C14B 1.792(13) . ?
S2B C13B 1.804(12) . ?
O1B C1B 1.198(14) . ?
O2B C1B 1.317(15) . ?
O2B H20B 0.86(3) . ?
O3B C10B 1.239(12) . ?
O4B C10B 1.301(13) . ?
O4B H21B 0.84(3) . ?
N1B C11B 1.419(16) . ?
N1B H22B 0.8600 . ?
C1B C2B 1.521(18) . ?
C1B C2D 1.57(4) . ?
C2B C3B 1.27(2) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.48(2) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.42(2) . ?
C4B C9B 1.431(19) . ?
C5B C6B 1.39(3) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.351(19) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.40(2) . ?
C8B C9B 1.35(2) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.556(15) . ?
C11B C12B 1.572(16) . ?
C11B H11B 0.9800 . ?
C12B C13B 1.511(17) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B H13B 0.9700 . ?
C13B H13C 0.9700 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
S1C O6C 1.44(7) . ?
S1C O5C 1.49(8) . ?
S1C C7C 1.71(6) . ?
C2C C3C 1.58(3) . ?
C2C C3D 1.59(3) . ?
C2C H2C 0.9800 . ?
C3C C4C 1.49(4) . ?
C3C C2D 1.57(3) . ?
C3C H3C 0.9800 . ?
C4C C9C 1.39(3) . ?
C4C C5C 1.40(3) . ?
C5C C6C 1.34(3) . ?
C5C H5C 0.9300 . ?
C6C C7C 1.43(3) . ?
C6C H6C 0.9300 . ?
C7C C8C 1.36(3) . ?
C8C C9C 1.38(3) . ?
C8C H8C 0.9300 . ?
C9C H9C 0.9300 . ?
S1D O6D 1.29(7) . ?
S1D O5D 1.64(7) . ?
S1D C7D 1.84(5) . ?
C2D C3D 1.57(3) . ?
C2D H2D 0.9800 . ?
C3D C4D 1.49(4) . ?
C3D H3D 0.9800 . ?
C4D C5D 1.42(3) . ?
C4D C9D 1.44(3) . ?
C5D C6D 1.39(3) . ?
C5D H5D 0.9300 . ?
C6D C7D 1.36(3) . ?
C6D H6D 0.9300 . ?
C7D C8D 1.41(3) . ?
C8D C9D 1.35(3) . ?
C8D H8D 0.9300 . ?
C9D H9D 0.9300 . ?
 
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
O5A S1A O6A 120.3(6) . . ?
O5A S1A N1A 103.7(6) . . ?
O6A S1A N1A 109.1(6) . . ?
O5A S1A C7A 109.3(6) . . ?
O6A S1A C7A 106.5(7) . . ?
N1A S1A C7A 107.3(6) . . ?
C1A O2A H20A 114(2) . . ?
C10A O4A H21A 105(10) . . ?
C11A N1A S1A 122.0(8) . . ?
C11A N1A H22A 119.0 . . ?
S1A N1A H22A 119.0 . . ?
O1A C1A O2A 124.4(12) . . ?
O1A C1A C2A 116.1(11) . . ?
O2A C1A C2A 119.1(10) . . ?
O1A C1A C2C 116.4(14) . . ?
O2A C1A C2C 106.0(13) . . ?
C3A C2A C1A 122.9(12) . . ?
C3A C2A H2A 118.5 . . ?
C1A C2A H2A 118.5 . . ?
C2A C3A C4A 127.5(12) . . ?
C2A C3A H3A 116.3 . . ?
C4A C3A H3A 116.3 . . ?
C9A C4A C5A 119.3(12) . . ?
C9A C4A C3A 119.7(12) . . ?
C5A C4A C3A 120.9(11) . . ?
C6A C5A C4A 120.2(11) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C5A C6A C7A 119.9(11) . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C8A C7A C6A 120.4(12) . . ?
C8A C7A S1A 119.7(10) . . ?
C6A C7A S1A 119.9(10) . . ?
C7A C8A C9A 118.8(11) . . ?
C7A C8A H8A 120.6 . . ?
C9A C8A H8A 120.6 . . ?
C4A C9A C8A 121.2(12) . . ?
C4A C9A H9A 119.4 . . ?
C8A C9A H9A 119.4 . . ?
O3A C10A O4A 125.2(11) . . ?
O3A C10A C11A 121.8(10) . . ?
O4A C10A C11A 112.9(9) . . ?
N1A C11A C12A 110.8(9) . . ?
N1A C11A C10A 112.8(8) . . ?
C12A C11A C10A 108.6(9) . . ?
N1A C11A H11A 108.2 . . ?
C12A C11A H11A 108.2 . . ?
C10A C11A H11A 108.2 . . ?
C11A C12A C13A 116.3(11) . . ?
C11A C12A H12A 108.2 . . ?
C13A C12A H12A 108.2 . . ?
C11A C12A H12B 108.2 . . ?
C13A C12A H12B 108.2 . . ?
H12A C12A H12B 107.4 . . ?
C12A C13A C15A 110.9(12) . . ?
C12A C13A C14A 108.8(11) . . ?
C15A C13A C14A 110.6(13) . . ?
C12A C13A H13A 108.8 . . ?
C15A C13A H13A 108.8 . . ?
C14A C13A H13A 108.8 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O5B S1B O6B 118.0(11) . . ?
O5B S1B N1B 111.6(11) . . ?
O6B S1B N1B 106.7(8) . . ?
O5B S1B C7B 108.4(10) . . ?
O6B S1B C7B 103.8(8) . . ?
N1B S1B C7B 107.6(7) . . ?
C14B S2B C13B 99.8(6) . . ?
C1B O2B H20B 110(10) . . ?
C10B O4B H21B 114(2) . . ?
C11B N1B S1B 127.2(9) . . ?
C11B N1B H22B 116.4 . . ?
S1B N1B H22B 116.4 . . ?
O1B C1B O2B 123.7(11) . . ?
O1B C1B C2B 120.8(11) . . ?
O2B C1B C2B 115.4(10) . . ?
O1B C1B C2D 124.2(17) . . ?
O2B C1B C2D 94.7(17) . . ?
C3B C2B C1B 123.1(14) . . ?
C3B C2B H2B 118.4 . . ?
C1B C2B H2B 118.4 . . ?
C2B C3B C4B 125.2(16) . . ?
C2B C3B H3B 117.4 . . ?
C4B C3B H3B 117.4 . . ?
C5B C4B C9B 118.0(14) . . ?
C5B C4B C3B 124.2(13) . . ?
C9B C4B C3B 117.7(14) . . ?
C6B C5B C4B 121.4(14) . . ?
C6B C5B H5B 119.3 . . ?
C4B C5B H5B 119.3 . . ?
C7B C6B C5B 116.7(17) . . ?
C7B C6B H6B 121.6 . . ?
C5B C6B H6B 121.6 . . ?
C6B C7B C8B 125.1(17) . . ?
C6B C7B S1B 115.3(14) . . ?
C8B C7B S1B 119.2(10) . . ?
C9B C8B C7B 118.2(13) . . ?
C9B C8B H8B 120.9 . . ?
C7B C8B H8B 120.9 . . ?
C8B C9B C4B 120.5(15) . . ?
C8B C9B H9B 119.7 . . ?
C4B C9B H9B 119.7 . . ?
O3B C10B O4B 123.6(10) . . ?
O3B C10B C11B 120.9(9) . . ?
O4B C10B C11B 115.3(8) . . ?
N1B C11B C10B 113.9(9) . . ?
N1B C11B C12B 111.2(10) . . ?
C10B C11B C12B 107.7(10) . . ?
N1B C11B H11B 107.9 . . ?
C10B C11B H11B 107.9 . . ?
C12B C11B H11B 107.9 . . ?
C13B C12B C11B 114.3(10) . . ?
C13B C12B H12C 108.7 . . ?
C11B C12B H12C 108.7 . . ?
C13B C12B H12D 108.7 . . ?
C11B C12B H12D 108.7 . . ?
H12C C12B H12D 107.6 . . ?
C12B C13B S2B 114.2(8) . . ?
C12B C13B H13B 108.7 . . ?
S2B C13B H13B 108.7 . . ?
C12B C13B H13C 108.7 . . ?
S2B C13B H13C 108.7 . . ?
H13B C13B H13C 107.6 . . ?
S2B C14B H14D 109.5 . . ?
S2B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
S2B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O6C S1C O5C 110(5) . . ?
O6C S1C C7C 119(4) . . ?
O5C S1C C7C 121(5) . . ?
C3C C2C C3D 90(2) . . ?
C3C C2C C1A 113(2) . . ?
C3D C2C C1A 120(2) . . ?
C3C C2C H2C 111.1 . . ?
C3D C2C H2C 111.1 . . ?
C1A C2C H2C 111.1 . . ?
C4C C3C C2D 123(3) . . ?
C4C C3C C2C 117(3) . . ?
C2D C3C C2C 90(2) . . ?
C4C C3C H3C 108.4 . . ?
C2D C3C H3C 108.4 . . ?
C2C C3C H3C 108.4 . . ?
C9C C4C C5C 115(3) . . ?
C9C C4C C3C 115(4) . . ?
C5C C4C C3C 130(4) . . ?
C6C C5C C4C 124(3) . . ?
C6C C5C H5C 118.1 . . ?
C4C C5C H5C 118.1 . . ?
C5C C6C C7C 119(3) . . ?
C5C C6C H6C 120.5 . . ?
C7C C6C H6C 120.5 . . ?
C8C C7C C6C 119(3) . . ?
C8C C7C S1C 123(4) . . ?
C6C C7C S1C 118(4) . . ?
C7C C8C C9C 120(3) . . ?
C7C C8C H8C 120.0 . . ?
C9C C8C H8C 120.0 . . ?
C8C C9C C4C 123(3) . . ?
C8C C9C H9C 118.4 . . ?
C4C C9C H9C 118.4 . . ?
O6D S1D O5D 137(5) . . ?
O6D S1D C7D 111(4) . . ?
O5D S1D C7D 104(3) . . ?
C1B C2D C3C 122(3) . . ?
C1B C2D C3D 117(2) . . ?
C3C C2D C3D 90(2) . . ?
C1B C2D H2D 108.5 . . ?
C3C C2D H2D 108.5 . . ?
C3D C2D H2D 108.5 . . ?
C4D C3D C2D 117(3) . . ?
C4D C3D C2C 115(3) . . ?
C2D C3D C2C 90(2) . . ?
C4D C3D H3D 111.2 . . ?
C2D C3D H3D 111.2 . . ?
C2C C3D H3D 111.2 . . ?
C5D C4D C9D 118(3) . . ?
C5D C4D C3D 126(3) . . ?
C9D C4D C3D 116(3) . . ?
C6D C5D C4D 120(3) . . ?
C6D C5D H5D 120.1 . . ?
C4D C5D H5D 120.1 . . ?
C7D C6D C5D 119(3) . . ?
C7D C6D H6D 120.4 . . ?
C5D C6D H6D 120.4 . . ?
C6D C7D C8D 124(3) . . ?
C6D C7D S1D 123(3) . . ?
C8D C7D S1D 113(3) . . ?
C9D C8D C7D 116(3) . . ?
C9D C8D H8D 121.9 . . ?
C7D C8D H8D 121.9 . . ?
C8D C9D C4D 122(3) . . ?
C8D C9D H9D 118.9 . . ?
C4D C9D H9D 118.9 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O5A S1A N1A C11A 178.7(9) . . . . ?
O6A S1A N1A C11A -51.9(10) . . . . ?
C7A S1A N1A C11A 63.1(10) . . . . ?
O1A C1A C2A C3A 179.4(11) . . . . ?
O2A C1A C2A C3A -7.7(19) . . . . ?
C2C C1A C2A C3A 76.8(19) . . . . ?
C1A C2A C3A C4A -177.7(12) . . . . ?
C2A C3A C4A C9A -178.0(14) . . . . ?
C2A C3A C4A C5A 4(2) . . . . ?
C9A C4A C5A C6A -1.2(18) . . . . ?
C3A C4A C5A C6A 176.6(15) . . . . ?
C4A C5A C6A C7A -0.3(19) . . . . ?
C5A C6A C7A C8A 3(2) . . . . ?
C5A C6A C7A S1A -174.1(12) . . . . ?
O5A S1A C7A C8A 157.6(12) . . . . ?
O6A S1A C7A C8A 26.3(15) . . . . ?
N1A S1A C7A C8A -90.5(13) . . . . ?
O5A S1A C7A C6A -25.0(14) . . . . ?
O6A S1A C7A C6A -156.4(12) . . . . ?
N1A S1A C7A C6A 86.9(13) . . . . ?
C6A C7A C8A C9A -5(2) . . . . ?
S1A C7A C8A C9A 172.8(14) . . . . ?
C5A C4A C9A C8A 0(2) . . . . ?
C3A C4A C9A C8A -178.0(15) . . . . ?
C7A C8A C9A C4A 3(3) . . . . ?
S1A N1A C11A C12A 159.7(8) . . . . ?
S1A N1A C11A C10A -78.3(11) . . . . ?
O3A C10A C11A N1A -31.5(15) . . . . ?
O4A C10A C11A N1A 150.2(10) . . . . ?
O3A C10A C11A C12A 91.7(13) . . . . ?
O4A C10A C11A C12A -86.5(11) . . . . ?
N1A C11A C12A C13A -63.5(14) . . . . ?
C10A C11A C12A C13A 172.0(10) . . . . ?
C11A C12A C13A C15A -63.7(17) . . . . ?
C11A C12A C13A C14A 174.5(10) . . . . ?
O5B S1B N1B C11B 173.4(12) . . . . ?
O6B S1B N1B C11B 43.2(12) . . . . ?
C7B S1B N1B C11B -67.7(11) . . . . ?
O1B C1B C2B C3B -177.2(15) . . . . ?
O2B C1B C2B C3B 5(2) . . . . ?
C2D C1B C2B C3B -67(2) . . . . ?
C1B C2B C3B C4B -179.7(14) . . . . ?
C2B C3B C4B C5B -7(3) . . . . ?
C2B C3B C4B C9B 176.9(15) . . . . ?
C9B C4B C5B C6B -0.5(16) . . . . ?
C3B C4B C5B C6B -176.4(15) . . . . ?
C4B C5B C6B C7B 1.4(18) . . . . ?
C5B C6B C7B C8B -1(2) . . . . ?
C5B C6B C7B S1B 171.7(11) . . . . ?
O5B S1B C7B C6B 37.3(18) . . . . ?
O6B S1B C7B C6B 163.5(14) . . . . ?
N1B S1B C7B C6B -83.7(14) . . . . ?
O5B S1B C7B C8B -149.4(16) . . . . ?
O6B S1B C7B C8B -23.2(17) . . . . ?
N1B S1B C7B C8B 89.6(15) . . . . ?
C6B C7B C8B C9B 0(3) . . . . ?
S1B C7B C8B C9B -172.7(13) . . . . ?
C7B C8B C9B C4B 1(2) . . . . ?
C5B C4B C9B C8B -1(2) . . . . ?
C3B C4B C9B C8B 175.4(16) . . . . ?
S1B N1B C11B C10B 79.3(12) . . . . ?
S1B N1B C11B C12B -158.7(9) . . . . ?
O3B C10B C11B N1B 37.6(16) . . . . ?
O4B C10B C11B N1B -137.0(11) . . . . ?
O3B C10B C11B C12B -86.2(13) . . . . ?
O4B C10B C11B C12B 99.2(11) . . . . ?
N1B C11B C12B C13B 173.6(9) . . . . ?
C10B C11B C12B C13B -60.9(11) . . . . ?
C11B C12B C13B S2B -65.4(11) . . . . ?
C14B S2B C13B C12B -76.0(10) . . . . ?
O1A C1A C2C C3C -169.4(17) . . . . ?
O2A C1A C2C C3C 48(2) . . . . ?
C2A C1A C2C C3C -67.5(19) . . . . ?
O1A C1A C2C C3D 87(2) . . . . ?
O2A C1A C2C C3D -56(2) . . . . ?
C2A C1A C2C C3D -171(3) . . . . ?
C3D C2C C3C C4C -126(3) . . . . ?
C1A C2C C3C C4C 112(3) . . . . ?
C3D C2C C3C C2D 1.9(18) . . . . ?
C1A C2C C3C C2D -120(2) . . . . ?
C2D C3C C4C C9C 81(5) . . . . ?
C2C C3C C4C C9C -170(4) . . . . ?
C2D C3C C4C C5C -89(5) . . . . ?
C2C C3C C4C C5C 20(6) . . . . ?
C9C C4C C5C C6C 2(4) . . . . ?
C3C C4C C5C C6C 172(5) . . . . ?
C4C C5C C6C C7C 0(4) . . . . ?
C5C C6C C7C C8C -1(7) . . . . ?
C5C C6C C7C S1C -174(5) . . . . ?
O6C S1C C7C C8C 9(8) . . . . ?
O5C S1C C7C C8C 151(6) . . . . ?
O6C S1C C7C C6C -179(5) . . . . ?
O5C S1C C7C C6C -36(7) . . . . ?
C6C C7C C8C C9C -1(10) . . . . ?
S1C C7C C8C C9C 172(6) . . . . ?
C7C C8C C9C C4C 3(11) . . . . ?
C5C C4C C9C C8C -3(8) . . . . ?
C3C C4C C9C C8C -175(6) . . . . ?
O1B C1B C2D C3C -78(3) . . . . ?
O2B C1B C2D C3C 59(3) . . . . ?
C2B C1B C2D C3C 179(4) . . . . ?
O1B C1B C2D C3D 173(2) . . . . ?
O2B C1B C2D C3D -50(3) . . . . ?
C2B C1B C2D C3D 70(2) . . . . ?
C4C C3C C2D C1B -3(4) . . . . ?
C2C C3C C2D C1B -125(3) . . . . ?
C4C C3C C2D C3D 120(4) . . . . ?
C2C C3C C2D C3D -2.0(18) . . . . ?
C1B C2D C3D C4D -113(3) . . . . ?
C3C C2D C3D C4D 120(3) . . . . ?
C1B C2D C3D C2C 129(3) . . . . ?
C3C C2D C3D C2C 2.0(18) . . . . ?
C3C C2C C3D C4D -122(3) . . . . ?
C1A C2C C3D C4D -6(4) . . . . ?
C3C C2C C3D C2D -1.9(18) . . . . ?
C1A C2C C3D C2D 114(3) . . . . ?
C2D C3D C4D C5D 3(5) . . . . ?
C2C C3D C4D C5D 106(4) . . . . ?
C2D C3D C4D C9D -174(3) . . . . ?
C2C C3D C4D C9D -71(4) . . . . ?
C9D C4D C5D C6D 4(3) . . . . ?
C3D C4D C5D C6D -174(4) . . . . ?
C4D C5D C6D C7D -1(3) . . . . ?
C5D C6D C7D C8D 3(7) . . . . ?
C5D C6D C7D S1D -175(4) . . . . ?
O6D S1D C7D C6D 152(5) . . . . ?
O5D S1D C7D C6D -4(6) . . . . ?
O6D S1D C7D C8D -26(6) . . . . ?
O5D S1D C7D C8D 178(5) . . . . ?
C6D C7D C8D C9D -8(8) . . . . ?
S1D C7D C8D C9D 170(4) . . . . ?
C7D C8D C9D C4D 10(7) . . . . ?
C5D C4D C9D C8D -9(5) . . . . ?
C3D C4D C9D C8D 169(4) . . . . ?
 
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 
O2B H20B O3A  0.86(3) 1.85(4) 2.692(13) 166(10) .
O4A H21A O1B  0.85(3) 1.81(6) 2.634(12) 163(18) .
O2A H20A O3B  0.85(3) 1.84(4) 2.679(11) 168(9) .
O4B H21B O1A  0.84(3) 1.82(3) 2.652(11) 168(8) .
 
_refine_diff_density_max    0.806
_refine_diff_density_min   -0.526
_refine_diff_density_rms    0.099

_shelxl_version_number 2013-4



#==END

 
data_kaw111a
# quasiracmeate UV irradiated 11 hours

# start Validation Reply Form
_vrf_PLAT213_kaw111a
;
PROBLEM: Atom N1A             has ADP max/min Ratio .....        6.0 prolat
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT222_kaw111a
;
PROBLEM: Large Non-Solvent    H    Uiso(max)/Uiso(min) ..       10.0 Ratio 
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT312_kaw111a
;
PROBLEM: Strange C-O-H Geometry (C-O  <   1.25 Ang) .....        O1A       
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT316_kaw111a
;
PROBLEM: Too many H on C in C=N Moiety in Main Residue ..       C11A       
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT220_kaw111a
;
PROBLEM: Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        8.8 Ratio 
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT230_kaw111a
;
PROBLEM: Hirshfeld Test Diff for    S1A    --  N1A     ..       14.4 su    
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT234_kaw111a
;
PROBLEM: Large Hirshfeld Difference N1B    --  C11B    ..       0.28 Ang.  
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT241_kaw111a
;
PROBLEM: High      Ueq as Compared to Neighbors for .....        C1B Check 
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT245_kaw111a
;
PROBLEM: U(iso) H20A    Smaller than U(eq) O1A     by ...      0.066 AngSq 
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
_vrf_PLAT340_kaw111a
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0362 Ang.  
RESPONSE: Poor crystal/data quality due to UV exposure of sample.
;
# end Validation Reply Form

 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C29 H36 N2 O12 S3' 
_chemical_formula_sum
 'C29 H36 N2 O12 S3' 
_chemical_formula_weight          700.78

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            1
_space_group_name_H-M_alt         'P 1'
_space_group_name_Hall            'P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 
_cell_length_a                    6.9689(5)
_cell_length_b                    8.0453(5)
_cell_length_c                    14.9788(10)
_cell_angle_alpha                 93.118(3)
_cell_angle_beta                  101.808(3)
_cell_angle_gamma                 98.412(3)
_cell_volume                      810.11(9)
_cell_formula_units_Z             1
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     5945 
_cell_measurement_theta_min       3.025
_cell_measurement_theta_max       65.664
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.36
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.436          
_exptl_crystal_F_000              368
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_absorpt_coefficient_mu     2.658
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.302
_exptl_absorpt_correction_T_max   0.767
_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  8.33 
_diffrn_reflns_number             14694
_diffrn_reflns_av_unetI/netI      0.0682
_diffrn_reflns_av_R_equivalents   0.0581
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.025
_diffrn_reflns_theta_max          66.816
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.964
_diffrn_measured_fraction_theta_full  0.945
_diffrn_reflns_Laue_measured_fraction_max    0.964
_diffrn_reflns_Laue_measured_fraction_full   0.945
_diffrn_reflns_point_group_measured_fraction_max   0.825
_diffrn_reflns_point_group_measured_fraction_full  0.809
_reflns_number_total              4755
_reflns_number_gt                 3278
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.712
_reflns_Friedel_fraction_max      0.686
_reflns_Friedel_fraction_full     0.672
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

Crystal irradiated using a 200W Xe(Hg) lamp for 240, 660, and 1320 min to
 give a crystal with noticable fractures. This sample represents
 660 min and 44% conversion.  Data collection was carried out
 at room temperature to minimize/exclude thermal shock that
 can result in sample degredation.  The diffraction pattern showed the
 expected signs of crystal twinning. Because the dominant twin component
 was considerably stronger and well dispersed from the minor component
 reflections, data were harvested as untwinned data.   

All non-hydrogen atoms were located in a series of difference density maps.
 Reaction progress was determined by the refinement of occupancy factors
 of the reactant and photodimer components.  Non-H atoms associated with 
 the major component (reactant) were refined using anisotropic
 displacement parameters while the minor component (photodimer) was refined
 using isotropic parameters. Each C-H hydrogen atom was placed in 
 calculated positions with Ueq = 1.2 x Uiso (1.5 x Uiso for methyl H
 atoms).  The remaining H atoms (O-H and N-H) were located in difference
 denisty maps and refined with Ueq = 1.2 x Uiso of the
 corresponding N/O atom and N/O-H distances restrained to 0.85(2) angstroms.

Addiional constraints to the structural model include:
FLAT - four phenyl and four carboxylic acid groups
RIGU - two reactant phenyl groups
SADI - cyclobutane C atoms and carboxylic acid groups


;
 
_computing_data_collection        'APEX2'
_computing_cell_refinement        'APEX2'
_computing_data_reduction         'APEX2'
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material   'XSEED (Barbour, 2001)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1156P)²+2.1233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.22(2)
_chemical_absolute_configuration  rm
_refine_ls_number_reflns          4755
_refine_ls_number_parameters      499
_refine_ls_number_restraints      160
_refine_ls_R_factor_all           0.1501
_refine_ls_R_factor_gt            0.1133
_refine_ls_wR_factor_ref          0.3106
_refine_ls_wR_factor_gt           0.2823
_refine_ls_goodness_of_fit_ref    1.064
_refine_ls_restrained_S_all       1.051
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1A S 0.1339(9) 0.6550(6) 0.9747(5) 0.123(2) Uani 1 1 d . . . . .
O1A O -0.410(3) -0.1700(16) 0.5259(8) 0.126(6) Uani 1 1 d D . . . .
O2A O -0.2332(16) -0.2998(14) 0.6311(8) 0.085(3) Uani 1 1 d D . . . .
O3A O -0.333(3) 0.383(3) 0.9709(14) 0.166(8) Uani 1 1 d D . . . .
O4A O -0.168(3) 0.2402(19) 1.0818(10) 0.119(5) Uani 1 1 d D . . . .
O5A O 0.127(3) 0.7898(15) 0.9174(16) 0.173(9) Uani 1 1 d . . . . .
O6A O 0.3151(19) 0.6468(16) 1.0340(13) 0.152(7) Uani 1 1 d . . . . .
N1A N -0.055(2) 0.6572(19) 1.0344(9) 0.091(5) Uani 1 1 d . . . . .
H1A H -0.1272 0.7381 1.0272 0.109 Uiso 1 1 calc R U . . .
C1A C -0.3139(19) -0.1763(19) 0.5999(9) 0.061(4) Uani 1 1 d . . . . .
C2A C -0.245(3) -0.011(4) 0.6638(19) 0.076(8) Uani 0.559(15) 1 d . U P A 1
H2A H -0.3121 0.0797 0.6442 0.091 Uiso 0.559(15) 1 calc R U P A 1
C3A C -0.112(3) 0.026(3) 0.7386(19) 0.060(6) Uani 0.559(15) 1 d . U P A 1
H3A H -0.0438 -0.0636 0.7592 0.072 Uiso 0.559(15) 1 calc R U P A 1
C4A C -0.055(5) 0.175(3) 0.793(2) 0.071(9) Uani 0.559(15) 1 d D U P A 1
C5A C -0.125(5) 0.331(4) 0.772(2) 0.16(3) Uani 0.559(15) 1 d D U P A 1
H5A H -0.2134 0.3353 0.7148 0.195 Uiso 0.559(15) 1 calc R U P A 1
C6A C -0.069(3) 0.471(3) 0.8311(18) 0.050(5) Uani 0.559(15) 1 d D U P A 1
H6A H -0.1210 0.5699 0.8145 0.060 Uiso 0.559(15) 1 calc R U P A 1
C7A C 0.059(3) 0.476(3) 0.9135(16) 0.048(5) Uani 0.559(15) 1 d D U P A 1
C8A C 0.123(4) 0.324(2) 0.937(2) 0.050(6) Uani 0.559(15) 1 d D U P A 1
H8A H 0.2029 0.3198 0.9961 0.060 Uiso 0.559(15) 1 calc R U P A 1
C9A C 0.076(6) 0.185(4) 0.879(3) 0.14(2) Uani 0.559(15) 1 d D U P A 1
H9A H 0.1335 0.0890 0.8961 0.162 Uiso 0.559(15) 1 calc R U P A 1
C10A C -0.212(2) 0.369(3) 1.0470(15) 0.108(7) Uani 1 1 d . . . . .
C11A C -0.093(3) 0.540(3) 1.0908(12) 0.096(6) Uani 1 1 d . . . . .
H11A H 0.0388 0.5172 1.1242 0.115 Uiso 1 1 calc R U . . .
C12A C -0.199(4) 0.596(3) 1.1638(15) 0.120(8) Uani 1 1 d . . . . .
H12A H -0.2341 0.4969 1.1971 0.144 Uiso 1 1 calc R U . . .
H12B H -0.3254 0.6292 1.1322 0.144 Uiso 1 1 calc R U . . .
C13A C -0.089(5) 0.742(3) 1.2355(19) 0.161(11) Uani 1 1 d . . . . .
H13A H -0.0397 0.8368 1.2011 0.193 Uiso 1 1 calc R U . . .
C14A C -0.245(4) 0.802(3) 1.2827(19) 0.161(11) Uani 1 1 d . . . . .
H14A H -0.2382 0.7529 1.3414 0.241 Uiso 1 1 calc R U . . .
H14B H -0.3770 0.7661 1.2436 0.241 Uiso 1 1 calc R U . . .
H14C H -0.2182 0.9253 1.2931 0.241 Uiso 1 1 calc R U . . .
C15A C 0.082(8) 0.697(4) 1.294(3) 0.28(3) Uani 1 1 d . . . . .
H15A H 0.0392 0.6248 1.3395 0.426 Uiso 1 1 calc R U . . .
H15B H 0.1685 0.7992 1.3258 0.426 Uiso 1 1 calc R U . . .
H15C H 0.1550 0.6357 1.2576 0.426 Uiso 1 1 calc R U . . .
S1B S -0.8570(11) -0.8687(9) 0.5279(5) 0.133(2) Uani 1 1 d . . . . .
S2B S -0.6528(12) -0.7367(9) 0.1933(5) 0.149(3) Uani 1 1 d . . . . .
O1B O -0.3045(18) -0.0521(15) 0.9846(9) 0.095(4) Uani 1 1 d D . . . .
O2B O -0.482(2) 0.0778(17) 0.8777(9) 0.105(4) Uani 1 1 d D . . . .
O3B O -0.3804(16) -0.5991(15) 0.5367(8) 0.087(3) Uani 1 1 d D . . . .
O4B O -0.531(3) -0.4684(18) 0.4230(9) 0.131(6) Uani 1 1 d D . . . .
O5B O -0.874(4) -1.004(3) 0.5808(14) 0.205(10) Uani 1 1 d . . . . .
O6B O -1.017(3) -0.834(2) 0.4593(12) 0.135(6) Uani 1 1 d . . . . .
N1B N -0.692(3) -0.870(2) 0.4846(14) 0.142(9) Uani 1 1 d . . . . .
H1B H -0.6172 -0.9457 0.5028 0.171 Uiso 1 1 calc R U . . .
C1B C -0.410(4) -0.047(4) 0.9051(18) 0.145(10) Uani 1 1 d . . . . .
C2B C -0.505(4) -0.236(3) 0.8539(14) 0.066(7) Uani 0.559(15) 1 d . U P A 1
H2B H -0.4910 -0.3343 0.8853 0.080 Uiso 0.559(15) 1 calc R U P A 1
C3B C -0.593(4) -0.245(4) 0.7760(16) 0.079(8) Uani 0.559(15) 1 d . U P A 1
H3B H -0.6136 -0.1429 0.7496 0.094 Uiso 0.559(15) 1 calc R U P A 1
C4B C -0.672(3) -0.408(3) 0.7167(15) 0.067(6) Uani 0.559(15) 1 d D U P A 1
C5B C -0.625(3) -0.568(3) 0.7465(13) 0.061(5) Uani 0.559(15) 1 d D U P A 1
H5B H -0.5446 -0.5723 0.8054 0.073 Uiso 0.559(15) 1 calc R U P A 1
C6B C -0.691(3) -0.703(4) 0.6939(14) 0.072(6) Uani 0.559(15) 1 d D U P A 1
H6B H -0.6680 -0.8097 0.7143 0.086 Uiso 0.559(15) 1 calc R U P A 1
C7B C -0.802(4) -0.691(4) 0.6034(13) 0.067(6) Uani 0.559(15) 1 d D U P A 1
C8B C -0.865(3) -0.555(3) 0.5744(15) 0.063(6) Uani 0.559(15) 1 d D U P A 1
H8B H -0.9525 -0.5570 0.5167 0.075 Uiso 0.559(15) 1 calc R U P A 1
C9B C -0.794(3) -0.399(3) 0.6347(15) 0.061(5) Uani 0.559(15) 1 d D U P A 1
H9B H -0.8334 -0.2948 0.6170 0.074 Uiso 0.559(15) 1 calc R U P A 1
C10B C -0.496(4) -0.598(2) 0.4632(10) 0.110(8) Uani 1 1 d . . . . .
C11B C -0.625(3) -0.767(2) 0.4152(14) 0.093(6) Uani 1 1 d . . . . .
H11B H -0.7435 -0.7401 0.3719 0.112 Uiso 1 1 calc R U . . .
C12B C -0.500(3) -0.862(3) 0.3592(16) 0.126(9) Uani 1 1 d . . . . .
H12C H -0.3774 -0.8812 0.4010 0.151 Uiso 1 1 calc R U . . .
H12D H -0.5782 -0.9738 0.3341 0.151 Uiso 1 1 calc R U . . .
C13B C -0.448(3) -0.772(4) 0.2853(15) 0.132(8) Uani 1 1 d . . . . .
H13B H -0.3592 -0.8343 0.2576 0.158 Uiso 1 1 calc R U . . .
H13C H -0.3706 -0.6607 0.3114 0.158 Uiso 1 1 calc R U . . .
C14B C -0.692(5) -0.931(3) 0.1343(16) 0.153(10) Uani 1 1 d . . . . .
H14F H -0.7309 -1.0182 0.1735 0.230 Uiso 1 1 calc R U . . .
H14E H -0.5696 -0.9515 0.1161 0.230 Uiso 1 1 calc R U . . .
H14D H -0.7981 -0.9357 0.0796 0.230 Uiso 1 1 calc R U . . .
C2C C -0.371(3) -0.063(3) 0.6729(13) 0.033(5) Uiso 0.441(15) 1 d D . P A 2
H2C H -0.4120 0.0437 0.6505 0.040 Uiso 0.441(15) 1 calc R U P A 2
C3C C -0.198(4) -0.036(3) 0.7582(14) 0.039(6) Uiso 0.441(15) 1 d D . P A 2
H3C H -0.0965 -0.1078 0.7497 0.047 Uiso 0.441(15) 1 calc R U P A 2
C4C C -0.097(5) 0.134(4) 0.802(2) 0.068(13) Uiso 0.441(15) 1 d D . P A 2
C5C C -0.142(4) 0.289(4) 0.7655(18) 0.055(9) Uiso 0.441(15) 1 d D . P A 2
H5C H -0.2451 0.2835 0.7126 0.065 Uiso 0.441(15) 1 calc R U P A 2
C6C C -0.041(5) 0.442(5) 0.804(2) 0.10(2) Uiso 0.441(15) 1 d D . P A 2
H6C H -0.0756 0.5401 0.7761 0.125 Uiso 0.441(15) 1 calc R U P A 2
C7C C 0.107(4) 0.461(3) 0.8807(18) 0.043(7) Uiso 0.441(15) 1 d D . P A 2
C8C C 0.157(7) 0.313(5) 0.917(3) 0.10(2) Uiso 0.441(15) 1 d D . P A 2
H8C H 0.2634 0.3200 0.9685 0.124 Uiso 0.441(15) 1 calc R U P A 2
C9C C 0.060(4) 0.161(3) 0.8794(18) 0.034(7) Uiso 0.441(15) 1 d D . P A 2
H9C H 0.1007 0.0644 0.9071 0.041 Uiso 0.441(15) 1 calc R U P A 2
C2D C -0.339(3) -0.124(4) 0.8125(17) 0.059(8) Uiso 0.441(15) 1 d D . P A 2
H2D H -0.2965 -0.2347 0.8265 0.071 Uiso 0.441(15) 1 calc R U P A 2
C3D C -0.511(3) -0.157(3) 0.7279(12) 0.033(5) Uiso 0.441(15) 1 d D . P A 2
H3D H -0.6113 -0.0842 0.7368 0.039 Uiso 0.441(15) 1 calc R U P A 2
C4D C -0.622(4) -0.331(4) 0.686(2) 0.069(9) Uiso 0.441(15) 1 d D . P A 2
C5D C -0.563(4) -0.477(5) 0.726(2) 0.085(11) Uiso 0.441(15) 1 d D . P A 2
H5D H -0.4780 -0.4643 0.7847 0.101 Uiso 0.441(15) 1 calc R U P A 2
C6D C -0.623(5) -0.625(5) 0.684(2) 0.079(11) Uiso 0.441(15) 1 d D . P A 2
H6D H -0.5808 -0.7212 0.7106 0.095 Uiso 0.441(15) 1 calc R U P A 2
C7D C -0.755(7) -0.642(5) 0.595(3) 0.109(19) Uiso 0.441(15) 1 d D . P A 2
C8D C -0.813(6) -0.514(4) 0.552(2) 0.088(14) Uiso 0.441(15) 1 d D . P A 2
H8D H -0.8951 -0.5296 0.4919 0.105 Uiso 0.441(15) 1 calc R U P A 2
C9D C -0.745(4) -0.346(4) 0.601(2) 0.068(9) Uiso 0.441(15) 1 d D . P A 2
H9D H -0.7855 -0.2492 0.5740 0.081 Uiso 0.441(15) 1 calc R U P A 2
H21A H -0.384(14) 0.285(5) 0.946(5) 0.4(4) Uiso 1 1 d D . . . .
H21B H -0.319(12) -0.504(5) 0.563(4) 0.12(7) Uiso 1 1 d D . . . .
H20A H -0.414(11) -0.252(7) 0.487(2) 0.06(4) Uiso 1 1 d D . . . .
H20B H -0.284(15) 0.039(7) 1.020(3) 0.8(9) Uiso 1 1 d D . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1A O6A 1.400(13) . ?
S1A O5A 1.420(15) . ?
S1A C7A 1.62(2) . ?
S1A N1A 1.735(17) . ?
O1A C1A 1.179(17) . ?
O1A H20A 0.85(3) . ?
O2A C1A 1.277(17) . ?
O3A C10A 1.30(3) . ?
O3A H21A 0.85(3) . ?
O4A C10A 1.23(3) . ?
N1A C11A 1.33(2) . ?
N1A H1A 0.8800 . ?
C1A C2C 1.53(3) . ?
C1A C2A 1.55(3) . ?
C2A C3A 1.29(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.37(3) . ?
C3A H3A 0.9500 . ?
C4A C9A 1.41(3) . ?
C4A C5A 1.44(3) . ?
C5A C6A 1.35(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.36(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.40(2) . ?
C8A C9A 1.34(3) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.54(3) . ?
C11A C12A 1.52(3) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.54(3) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C15A 1.43(4) . ?
C13A C14A 1.53(4) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
S1B O5B 1.388(19) . ?
S1B O6B 1.428(18) . ?
S1B N1B 1.43(2) . ?
S1B C7B 1.72(3) . ?
S2B C14B 1.71(2) . ?
S2B C13B 1.84(2) . ?
O1B C1B 1.27(3) . ?
O1B H20B 0.85(3) . ?
O2B C1B 1.24(3) . ?
O3B C10B 1.226(19) . ?
O3B H21B 0.85(3) . ?
O4B C10B 1.26(2) . ?
N1B C11B 1.47(3) . ?
N1B H1B 0.8800 . ?
C1B C2B 1.64(4) . ?
C1B C2D 1.68(4) . ?
C2B C3B 1.19(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.50(4) . ?
C3B H3B 0.9500 . ?
C4B C9B 1.36(3) . ?
C4B C5B 1.45(3) . ?
C5B C6B 1.28(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.43(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.30(3) . ?
C8B C9B 1.47(3) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.56(2) . ?
C11B C12B 1.57(3) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.43(3) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13B 0.9900 . ?
C13B H13C 0.9900 . ?
C14B H14F 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14D 0.9800 . ?
C2C C3D 1.54(2) . ?
C2C C3C 1.55(2) . ?
C2C H2C 1.0000 . ?
C3C C4C 1.49(4) . ?
C3C C2D 1.52(2) . ?
C3C H3C 1.0000 . ?
C4C C9C 1.41(3) . ?
C4C C5C 1.43(3) . ?
C5C C6C 1.36(4) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.36(3) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.39(3) . ?
C8C C9C 1.34(3) . ?
C8C H8C 0.9500 . ?
C9C H9C 0.9500 . ?
C2D C3D 1.54(2) . ?
C2D H2D 1.0000 . ?
C3D C4D 1.53(4) . ?
C3D H3D 1.0000 . ?
C4D C9D 1.37(3) . ?
C4D C5D 1.42(3) . ?
C5D C6D 1.29(3) . ?
C5D H5D 0.9500 . ?
C6D C7D 1.44(3) . ?
C6D H6D 0.9500 . ?
C7D C8D 1.31(3) . ?
C8D C9D 1.47(3) . ?
C8D H8D 0.9500 . ?
C9D H9D 0.9500 . ?
 
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 117.6(10) . . ?
O6A S1A C7A 108.5(10) . . ?
O5A S1A C7A 110.1(12) . . ?
O6A S1A N1A 111.1(11) . . ?
O5A S1A N1A 107.8(11) . . ?
C7A S1A N1A 100.5(10) . . ?
C1A O1A H20A 116(3) . . ?
C10A O3A H21A 108(3) . . ?
C11A N1A S1A 122.2(13) . . ?
C11A N1A H1A 118.9 . . ?
S1A N1A H1A 118.9 . . ?
O1A C1A O2A 127.5(13) . . ?
O1A C1A C2C 112.7(14) . . ?
O2A C1A C2C 114.1(13) . . ?
O1A C1A C2A 118.4(18) . . ?
O2A C1A C2A 113.3(15) . . ?
C3A C2A C1A 131(2) . . ?
C3A C2A H2A 114.3 . . ?
C1A C2A H2A 114.3 . . ?
C2A C3A C4A 129(2) . . ?
C2A C3A H3A 115.3 . . ?
C4A C3A H3A 115.3 . . ?
C3A C4A C9A 121(2) . . ?
C3A C4A C5A 125(2) . . ?
C9A C4A C5A 114(2) . . ?
C6A C5A C4A 122(2) . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C5A C6A C7A 123.2(19) . . ?
C5A C6A H6A 118.4 . . ?
C7A C6A H6A 118.4 . . ?
C6A C7A C8A 116.2(19) . . ?
C6A C7A S1A 119.0(16) . . ?
C8A C7A S1A 124.7(16) . . ?
C9A C8A C7A 122(2) . . ?
C9A C8A H8A 119.0 . . ?
C7A C8A H8A 119.0 . . ?
C8A C9A C4A 123(2) . . ?
C8A C9A H9A 118.3 . . ?
C4A C9A H9A 118.3 . . ?
O4A C10A O3A 129(2) . . ?
O4A C10A C11A 118.4(17) . . ?
O3A C10A C11A 112(2) . . ?
N1A C11A C12A 114.4(18) . . ?
N1A C11A C10A 117.1(16) . . ?
C12A C11A C10A 105.8(19) . . ?
N1A C11A H11A 106.3 . . ?
C12A C11A H11A 106.3 . . ?
C10A C11A H11A 106.3 . . ?
C11A C12A C13A 118(2) . . ?
C11A C12A H12A 107.8 . . ?
C13A C12A H12A 107.8 . . ?
C11A C12A H12B 107.8 . . ?
C13A C12A H12B 107.8 . . ?
H12A C12A H12B 107.2 . . ?
C15A C13A C14A 116(3) . . ?
C15A C13A C12A 112(2) . . ?
C14A C13A C12A 107(2) . . ?
C15A C13A H13A 107.1 . . ?
C14A C13A H13A 107.1 . . ?
C12A C13A H13A 107.1 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O5B S1B O6B 123.0(13) . . ?
O5B S1B N1B 110.6(14) . . ?
O6B S1B N1B 106.1(11) . . ?
O5B S1B C7B 105.9(14) . . ?
O6B S1B C7B 103.3(11) . . ?
N1B S1B C7B 106.7(12) . . ?
C14B S2B C13B 97.5(12) . . ?
C1B O1B H20B 115(3) . . ?
C10B O3B H21B 116(3) . . ?
S1B N1B C11B 131.8(17) . . ?
S1B N1B H1B 114.1 . . ?
C11B N1B H1B 114.1 . . ?
O2B C1B O1B 124(3) . . ?
O2B C1B C2B 120(2) . . ?
O1B C1B C2B 113(2) . . ?
O2B C1B C2D 103(2) . . ?
O1B C1B C2D 120(3) . . ?
C3B C2B C1B 118(2) . . ?
C3B C2B H2B 121.1 . . ?
C1B C2B H2B 121.1 . . ?
C2B C3B C4B 125(2) . . ?
C2B C3B H3B 117.7 . . ?
C4B C3B H3B 117.7 . . ?
C9B C4B C5B 121(2) . . ?
C9B C4B C3B 117(2) . . ?
C5B C4B C3B 122(2) . . ?
C6B C5B C4B 120(2) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C7B 118(2) . . ?
C5B C6B H6B 120.8 . . ?
C7B C6B H6B 120.8 . . ?
C8B C7B C6B 125(2) . . ?
C8B C7B S1B 117.7(17) . . ?
C6B C7B S1B 118(2) . . ?
C7B C8B C9B 117(2) . . ?
C7B C8B H8B 121.4 . . ?
C9B C8B H8B 121.4 . . ?
C4B C9B C8B 118(2) . . ?
C4B C9B H9B 121.2 . . ?
C8B C9B H9B 121.2 . . ?
O3B C10B O4B 125.9(16) . . ?
O3B C10B C11B 119.2(15) . . ?
O4B C10B C11B 114.8(16) . . ?
N1B C11B C10B 109.4(15) . . ?
N1B C11B C12B 111.6(18) . . ?
C10B C11B C12B 109.6(17) . . ?
N1B C11B H11B 108.7 . . ?
C10B C11B H11B 108.7 . . ?
C12B C11B H11B 108.7 . . ?
C13B C12B C11B 113.1(18) . . ?
C13B C12B H12C 109.0 . . ?
C11B C12B H12C 109.0 . . ?
C13B C12B H12D 109.0 . . ?
C11B C12B H12D 109.0 . . ?
H12C C12B H12D 107.8 . . ?
C12B C13B S2B 117.1(17) . . ?
C12B C13B H13B 108.0 . . ?
S2B C13B H13B 108.0 . . ?
C12B C13B H13C 108.0 . . ?
S2B C13B H13C 108.0 . . ?
H13B C13B H13C 107.3 . . ?
S2B C14B H14F 109.5 . . ?
S2B C14B H14E 109.5 . . ?
H14F C14B H14E 109.5 . . ?
S2B C14B H14D 109.5 . . ?
H14F C14B H14D 109.5 . . ?
H14E C14B H14D 109.5 . . ?
C1A C2C C3D 114.3(17) . . ?
C1A C2C C3C 108.0(17) . . ?
C3D C2C C3C 90.8(13) . . ?
C1A C2C H2C 113.8 . . ?
C3D C2C H2C 113.8 . . ?
C3C C2C H2C 113.8 . . ?
C4C C3C C2D 113(2) . . ?
C4C C3C C2C 123(2) . . ?
C2D C3C C2C 88.8(14) . . ?
C4C C3C H3C 110.0 . . ?
C2D C3C H3C 110.0 . . ?
C2C C3C H3C 110.0 . . ?
C9C C4C C5C 113(2) . . ?
C9C C4C C3C 124(3) . . ?
C5C C4C C3C 123(3) . . ?
C6C C5C C4C 122(2) . . ?
C6C C5C H5C 118.8 . . ?
C4C C5C H5C 118.8 . . ?
C5C C6C C7C 123(3) . . ?
C5C C6C H6C 118.7 . . ?
C7C C6C H6C 118.7 . . ?
C6C C7C C8C 116(3) . . ?
C9C C8C C7C 122(3) . . ?
C9C C8C H8C 119.2 . . ?
C7C C8C H8C 119.2 . . ?
C8C C9C C4C 124(2) . . ?
C8C C9C H9C 117.9 . . ?
C4C C9C H9C 117.9 . . ?
C3C C2D C3D 92.1(15) . . ?
C3C C2D C1B 129(2) . . ?
C3D C2D C1B 112(2) . . ?
C3C C2D H2D 107.3 . . ?
C3D C2D H2D 107.3 . . ?
C1B C2D H2D 107.3 . . ?
C4D C3D C2D 125(2) . . ?
C4D C3D C2C 116.5(19) . . ?
C2D C3D C2C 88.3(14) . . ?
C4D C3D H3D 108.2 . . ?
C2D C3D H3D 108.2 . . ?
C2C C3D H3D 108.2 . . ?
C9D C4D C5D 120(3) . . ?
C9D C4D C3D 119(3) . . ?
C5D C4D C3D 119(2) . . ?
C6D C5D C4D 121(3) . . ?
C6D C5D H5D 119.3 . . ?
C4D C5D H5D 119.3 . . ?
C5D C6D C7D 119(3) . . ?
C5D C6D H6D 120.7 . . ?
C7D C6D H6D 120.7 . . ?
C8D C7D C6D 124(3) . . ?
C7D C8D C9D 116(3) . . ?
C7D C8D H8D 121.8 . . ?
C9D C8D H8D 121.8 . . ?
C4D C9D C8D 119(3) . . ?
C4D C9D H9D 120.5 . . ?
C8D C9D H9D 120.5 . . ?
 
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 -53.2(15) . . . . ?
O5A S1A N1A C11A 176.6(15) . . . . ?
C7A S1A N1A C11A 61.4(15) . . . . ?
O1A C1A C2A C3A -165(3) . . . . ?
O2A C1A C2A C3A 5(4) . . . . ?
C2C C1A C2A C3A 105(4) . . . . ?
C1A C2A C3A C4A 180(3) . . . . ?
C2A C3A C4A C9A 172(3) . . . . ?
C2A C3A C4A C5A -5(5) . . . . ?
C3A C4A C5A C6A 177(4) . . . . ?
C9A C4A C5A C6A -0.8(17) . . . . ?
C4A C5A C6A C7A 1.0(17) . . . . ?
C5A C6A C7A C8A -3(3) . . . . ?
C5A C6A C7A S1A 174(2) . . . . ?
O6A S1A C7A C6A -156.3(18) . . . . ?
O5A S1A C7A C6A -26(2) . . . . ?
N1A S1A C7A C6A 87.2(19) . . . . ?
O6A S1A C7A C8A 20(3) . . . . ?
O5A S1A C7A C8A 150(2) . . . . ?
N1A S1A C7A C8A -96(2) . . . . ?
C6A C7A C8A C9A 5(4) . . . . ?
S1A C7A C8A C9A -171(3) . . . . ?
C7A C8A C9A C4A -6(5) . . . . ?
C3A C4A C9A C8A -175(4) . . . . ?
C5A C4A C9A C8A 3(4) . . . . ?
S1A N1A C11A C12A 156.7(15) . . . . ?
S1A N1A C11A C10A -79(2) . . . . ?
O4A C10A C11A N1A 143(2) . . . . ?
O3A C10A C11A N1A -30(3) . . . . ?
O4A C10A C11A C12A -88(2) . . . . ?
O3A C10A C11A C12A 98(2) . . . . ?
N1A C11A C12A C13A -64(3) . . . . ?
C10A C11A C12A C13A 166(2) . . . . ?
C11A C12A C13A C15A -66(4) . . . . ?
C11A C12A C13A C14A 165(2) . . . . ?
O5B S1B N1B C11B 172.5(19) . . . . ?
O6B S1B N1B C11B 37(2) . . . . ?
C7B S1B N1B C11B -73(2) . . . . ?
O2B C1B C2B C3B 25(4) . . . . ?
O1B C1B C2B C3B -174(3) . . . . ?
C2D C1B C2B C3B -62(3) . . . . ?
C1B C2B C3B C4B 174(2) . . . . ?
C2B C3B C4B C9B 170(3) . . . . ?
C2B C3B C4B C5B -8(3) . . . . ?
C9B C4B C5B C6B 3.3(14) . . . . ?
C3B C4B C5B C6B -178.7(15) . . . . ?
C4B C5B C6B C7B 3.8(14) . . . . ?
C5B C6B C7B C8B -10(3) . . . . ?
C5B C6B C7B S1B 170.2(15) . . . . ?
O5B S1B C7B C8B -149(2) . . . . ?
O6B S1B C7B C8B -19(2) . . . . ?
N1B S1B C7B C8B 93(2) . . . . ?
O5B S1B C7B C6B 30(2) . . . . ?
O6B S1B C7B C6B 161.0(17) . . . . ?
N1B S1B C7B C6B -87.4(19) . . . . ?
C6B C7B C8B C9B 9(3) . . . . ?
S1B C7B C8B C9B -171.9(17) . . . . ?
C5B C4B C9B C8B -5(2) . . . . ?
C3B C4B C9B C8B 177.1(17) . . . . ?
C7B C8B C9B C4B -1(3) . . . . ?
S1B N1B C11B C10B 84(2) . . . . ?
S1B N1B C11B C12B -154.7(16) . . . . ?
O3B C10B C11B N1B 39(3) . . . . ?
O4B C10B C11B N1B -137(2) . . . . ?
O3B C10B C11B C12B -84(2) . . . . ?
O4B C10B C11B C12B 100(2) . . . . ?
N1B C11B C12B C13B 174.5(16) . . . . ?
C10B C11B C12B C13B -64(2) . . . . ?
C11B C12B C13B S2B -64(2) . . . . ?
C14B S2B C13B C12B -81(2) . . . . ?
O1A C1A C2C C3D 98.6(19) . . . . ?
O2A C1A C2C C3D -56.8(19) . . . . ?
C2A C1A C2C C3D -154(3) . . . . ?
O1A C1A C2C C3C -162.0(17) . . . . ?
O2A C1A C2C C3C 43(2) . . . . ?
C2A C1A C2C C3C -54(2) . . . . ?
C1A C2C C3C C4C 126(3) . . . . ?
C3D C2C C3C C4C -118(3) . . . . ?
C1A C2C C3C C2D -117.6(18) . . . . ?
C3D C2C C3C C2D -2(2) . . . . ?
C2D C3C C4C C9C 76(3) . . . . ?
C2C C3C C4C C9C -180(2) . . . . ?
C2D C3C C4C C5C -109(3) . . . . ?
C2C C3C C4C C5C -5(4) . . . . ?
C9C C4C C5C C6C -0.8(16) . . . . ?
C3C C4C C5C C6C -177(3) . . . . ?
C4C C5C C6C C7C -1.1(19) . . . . ?
C5C C6C C7C C8C 3(4) . . . . ?
C6C C7C C8C C9C -3(5) . . . . ?
C7C C8C C9C C4C 1(5) . . . . ?
C5C C4C C9C C8C 1(4) . . . . ?
C3C C4C C9C C8C 177(3) . . . . ?
C4C C3C C2D C3D 128(2) . . . . ?
C2C C3C C2D C3D 2(2) . . . . ?
C4C C3C C2D C1B 7(3) . . . . ?
C2C C3C C2D C1B -119(2) . . . . ?
O2B C1B C2D C3C 57(3) . . . . ?
O1B C1B C2D C3C -86(3) . . . . ?
C2B C1B C2D C3C 175(3) . . . . ?
O2B C1B C2D C3D -55(3) . . . . ?
O1B C1B C2D C3D 162(2) . . . . ?
C2B C1B C2D C3D 63.0(19) . . . . ?
C3C C2D C3D C4D 120(2) . . . . ?
C1B C2D C3D C4D -106(3) . . . . ?
C3C C2D C3D C2C -2(2) . . . . ?
C1B C2D C3D C2C 132(2) . . . . ?
C1A C2C C3D C4D -18(2) . . . . ?
C3C C2C C3D C4D -128(2) . . . . ?
C1A C2C C3D C2D 111.8(18) . . . . ?
C3C C2C C3D C2D 2(2) . . . . ?
C2D C3D C4D C9D -167(2) . . . . ?
C2C C3D C4D C9D -59(3) . . . . ?
C2D C3D C4D C5D -1(3) . . . . ?
C2C C3D C4D C5D 107(2) . . . . ?
C9D C4D C5D C6D -0.2(18) . . . . ?
C3D C4D C5D C6D -166(3) . . . . ?
C4D C5D C6D C7D -0.9(18) . . . . ?
C5D C6D C7D C8D 3(4) . . . . ?
C6D C7D C8D C9D -3(5) . . . . ?
C5D C4D C9D C8D 0(3) . . . . ?
C3D C4D C9D C8D 165(3) . . . . ?
C7D C8D C9D C4D 2(4) . . . . ?
 
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 H20A O4B  0.85(3) 1.92(5) 2.707(19) 153(8) .
O3B H21B O2A  0.85(3) 1.84(4) 2.677(15) 167(10) .
O1B H20B O4A  0.85(3) 1.82(5) 2.639(19) 162(12) .
O3A H21A O2B  0.85(3) 1.87(4) 2.71(3) 172(10) .
 
_refine_diff_density_max    0.387
_refine_diff_density_min   -0.298
_refine_diff_density_rms    0.074

_shelxl_version_number 2013-4



#==END

 
data_kaw111b_twin4
# quasiracemate UV irradiated 22 hours 
 
# start Validation Reply Form
_vrf_PLAT220_kaw111b_twin4
;
PROBLEM: Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        5.4 Ratio 
RESPONSE: Large Ueq ratio due to crystal degredation from
UV exposure.
;
_vrf_PLAT340_kaw111b_twin4
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0142 Ang.  
RESPONSE: Low bond precisionarge due to crystal degredation from
UV exposure.
;
# end Validation Reply Form


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_absolute_configuration  rm
_chemical_formula_moiety          
 'C29 H36 N2 O12 S3' 
_chemical_formula_sum 
 'C29 H36 N2 O12 S3' 
_chemical_formula_weight          700.78 
 
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' 
 
_space_group_crystal_system       triclinic
_space_group_IT_number            1
_space_group_name_H-M_alt         'P 1'
_space_group_name_Hall            'P 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 
_cell_length_a                    6.8789(6) 
_cell_length_b                    8.1405(7) 
_cell_length_c                    14.5005(13) 
_cell_angle_alpha                 92.437(5) 
_cell_angle_beta                  98.844(5) 
_cell_angle_gamma                 99.960(5) 
_cell_volume                      788.25(12) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     8331
_cell_measurement_theta_min       2.812
_cell_measurement_theta_max       65.077
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'light yellow'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.36
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.476 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              368 
_exptl_absorpt_coefficient_mu     2.732 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.292
_exptl_absorpt_correction_T_max   0.761
_exptl_absorpt_process_details    
  'SADABS (Bruker, 2010)'
 
_exptl_special_details 
; 
 (L)-3/(D)-4-reacted is a different crystalline sample than that
 used for the crystallopgraphic determination of unreacted
 (L)-3/(D).
; 
 
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             24878 
_diffrn_reflns_av_R_equivalents   0.0733 
_diffrn_reflns_av_sigmaI/netI     0.0448 
_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        0 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          3.092
_diffrn_reflns_theta_max          67.553
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.941
_diffrn_measured_fraction_theta_full  0.938
_diffrn_reflns_Laue_measured_fraction_max    0.941
_diffrn_reflns_Laue_measured_fraction_full   0.938
_diffrn_reflns_point_group_measured_fraction_max   0.470
_diffrn_reflns_point_group_measured_fraction_full  0.469
_reflns_number_total              2680
_reflns_number_gt                 2263
_reflns_threshold_expression      >2sigma(I) 
 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

Crystal irradiated using a 200W Xe(Hg) lamp for 240, 660, and 1320 min to
 give a crystal with noticable fractures. This sample represents
 1320 min and 100% conversion.  Data collection was carried out
 at room temperature to minimize/exclude thermal shock and the
 ultimate degredation of the sample.  The diffraction pattern showed the
 expected signs of crystal twinning.  Data was integtrated using the
 program Cell_Now.  Since one twin component dominated the diffration
 pattern, reflections from this twin component (twin4) were used for structure
 solution and refinement.  A three component twin data set (twin5) was
 attempted with less satisfactory results.  

All non-hydrogen atoms were located in a difference density map. The Non-H
 atoms were refined using anisotropic displacement parameter.  Each H atom
 was placed in calculated positions with Ueq = 1.2 x Uiso
 (1.5 x Uiso for methyl H atoms).  The remaining H atoms (O-H and N-H) were
 located in difference denisty maps and refined with Ueq = 1.2 x Uiso of the
 corresponding N/O atom and N/O-H distances restrained to 0.85(2) angstroms.
 H5 was restrained using the FLAT command (O3B O4B C10B H5).
; 
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1587P)²+0.2856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack    0.05(4)
_refine_ls_number_reflns          2680
_refine_ls_number_parameters      438
_refine_ls_number_restraints      10
_refine_ls_R_factor_all           0.0857
_refine_ls_R_factor_gt            0.0747
_refine_ls_wR_factor_ref          0.2113
_refine_ls_wR_factor_gt           0.1964
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.067
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1A S 0.9999(3) -0.0001(2) 0.99955(14) 0.0497(5) Uani 1 1 d . . . . .
O1A O 0.6174(10) -0.9453(9) 0.6637(5) 0.0583(16) Uani 1 1 d . . . . .
O2A O 0.4325(13) -0.8097(9) 0.5615(5) 0.074(2) Uani 1 1 d D . . . .
H1 H 0.451(19) -0.871(14) 0.515(6) 0.089 Uiso 1 1 d D U . . .
O3A O 0.6658(14) -0.3965(11) 1.1278(6) 0.081(2) Uani 1 1 d . . . . .
O4A O 0.5146(11) -0.2473(10) 1.0181(6) 0.0685(19) Uani 1 1 d D . . . .
H2 H 0.466(18) -0.346(7) 0.994(8) 0.082 Uiso 1 1 d D U . . .
O5A O 1.1765(11) -0.0073(9) 1.0627(6) 0.072(2) Uani 1 1 d . . . . .
O6A O 0.9893(14) 0.1306(9) 0.9388(6) 0.076(2) Uani 1 1 d . . . . .
N1A N 0.8266(13) 0.0193(10) 1.0660(5) 0.056(2) Uani 1 1 d D . . . .
H3 H 0.737(12) 0.049(13) 1.026(6) 0.067 Uiso 1 1 d D U . . .
C1A C 0.5271(14) -0.8268(12) 0.6452(6) 0.050(2) Uani 1 1 d . . . . .
C2A C 0.4944(13) -0.7095(11) 0.7198(6) 0.0464(19) Uani 1 1 d . . . . .
H2A H 0.4632 -0.6049 0.6955 0.05(2) Uiso 1 1 calc R . . . .
C3A C 0.6532(11) -0.6789(9) 0.8084(5) 0.0348(15) Uani 1 1 d . . . . .
H3A H 0.7550 -0.7475 0.8024 0.042 Uiso 1 1 calc R U . . .
C4A C 0.7546(11) -0.5034(10) 0.8449(5) 0.0351(16) Uani 1 1 d . . . . .
C5A C 0.9037(11) -0.4858(11) 0.9217(5) 0.0404(17) Uani 1 1 d . . . . .
H5A H 0.9512 -0.5800 0.9429 0.048 Uiso 1 1 calc R U . . .
C6A C 0.9854(12) -0.3297(11) 0.9687(5) 0.0433(18) Uani 1 1 d . . . . .
H6A H 1.0823 -0.3203 1.0219 0.052 Uiso 1 1 calc R U . . .
C7A C 0.9196(12) -0.1902(10) 0.9347(5) 0.0398(17) Uani 1 1 d . . . . .
C8A C 0.7787(13) -0.2038(11) 0.8543(6) 0.0445(19) Uani 1 1 d . . . . .
H8A H 0.7393 -0.1083 0.8305 0.053 Uiso 1 1 calc R U . . .
C9A C 0.6966(12) -0.3585(11) 0.8095(6) 0.0423(18) Uani 1 1 d . . . . .
H9A H 0.6021 -0.3668 0.7555 0.051 Uiso 1 1 calc R U . . .
C10A C 0.6444(14) -0.2602(13) 1.0919(7) 0.055(2) Uani 1 1 d . . . . .
C11A C 0.7744(16) -0.1004(14) 1.1325(6) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.8979 -0.1256 1.1677 0.072 Uiso 1 1 calc R U . . .
C12A C 0.658(2) -0.0247(17) 1.2018(9) 0.083(4) Uani 1 1 d . . . . .
H12A H 0.5560 0.0264 1.1661 0.100 Uiso 1 1 calc R U . . .
H12B H 0.5898 -0.1153 1.2329 0.100 Uiso 1 1 calc R U . . .
C13A C 0.781(3) 0.1051(17) 1.2765(9) 0.101(5) Uani 1 1 d . . . . .
H13A H 0.8543 0.1904 1.2427 0.121 Uiso 1 1 calc R U . . .
C14A C 0.934(5) 0.045(3) 1.3415(15) 0.190(12) Uani 1 1 d . . . . .
H14A H 0.8893 -0.0712 1.3503 0.285 Uiso 1 1 calc R U . . .
H14B H 0.9570 0.1085 1.4005 0.285 Uiso 1 1 calc R U . . .
H14C H 1.0565 0.0567 1.3161 0.285 Uiso 1 1 calc R U . . .
C15A C 0.646(4) 0.195(3) 1.3272(14) 0.158(9) Uani 1 1 d . . . . .
H15A H 0.5170 0.1845 1.2885 0.236 Uiso 1 1 calc R U . . .
H15B H 0.7048 0.3109 1.3397 0.236 Uiso 1 1 calc R U . . .
H15C H 0.6299 0.1451 1.3851 0.236 Uiso 1 1 calc R U . . .
S1B S -0.0345(3) -1.4765(2) 0.58547(15) 0.0518(6) Uani 1 1 d . . . . .
S2B S 0.1915(7) -1.3813(5) 0.2310(2) 0.1053(12) Uani 1 1 d . . . . .
O1B O 0.3666(9) -0.5498(9) 0.9316(5) 0.0597(17) Uani 1 1 d . . . . .
O2B O 0.5674(12) -0.6865(10) 1.0244(5) 0.0662(19) Uani 1 1 d D . . . .
H4 H 0.590(18) -0.614(12) 1.071(6) 0.079 Uiso 1 1 d D U . . .
O3B O 0.3414(16) -1.1128(9) 0.4640(5) 0.090(3) Uani 1 1 d . . . . .
O4B O 0.4660(11) -1.2514(10) 0.5801(5) 0.0643(18) Uani 1 1 d D . . . .
H5 H 0.551(10) -1.167(9) 0.604(7) 0.077 Uiso 1 1 d D U . . .
O5B O -0.1964(11) -1.4541(10) 0.5177(7) 0.078(2) Uani 1 1 d . . . . .
O6B O -0.0556(11) -1.6070(8) 0.6498(6) 0.0682(19) Uani 1 1 d . . . . .
N1B N 0.1442(11) -1.5106(10) 0.5324(5) 0.0518(18) Uani 1 1 d D . . . .
H6 H 0.209(14) -1.590(9) 0.533(7) 0.062 Uiso 1 1 d D U . . .
C1B C 0.4662(14) -0.6645(13) 0.9455(6) 0.053(2) Uani 1 1 d . . . . .
C2B C 0.4943(12) -0.7719(10) 0.8670(6) 0.0442(18) Uani 1 1 d . . . . .
H2B H 0.5264 -0.8790 0.8869 0.053 Uiso 1 1 calc R U . . .
C3B C 0.3329(13) -0.7944(12) 0.7794(6) 0.049(2) Uani 1 1 d . . . . .
H3B H 0.2365 -0.7209 0.7864 0.059 Uiso 1 1 calc R U . . .
C4B C 0.2226(12) -0.9684(11) 0.7401(6) 0.0450(19) Uani 1 1 d . . . . .
C5B C 0.0835(13) -0.9831(11) 0.6590(7) 0.050(2) Uani 1 1 d . . . . .
H5B H 0.0476 -0.8871 0.6341 0.060 Uiso 1 1 calc R U . . .
C6B C -0.0026(12) -1.1367(11) 0.6148(7) 0.049(2) Uani 1 1 d . . . . .
H6B H -0.0952 -1.1448 0.5600 0.059 Uiso 1 1 calc R U . . .
C7B C 0.0505(11) -1.2810(10) 0.6530(6) 0.0438(19) Uani 1 1 d . . . . .
C8B C 0.1742(12) -1.2695(11) 0.7369(6) 0.0460(19) Uani 1 1 d . . . . .
H8B H 0.2001 -1.3661 0.7647 0.055 Uiso 1 1 calc R U . . .
C9B C 0.2614(12) -1.1141(10) 0.7809(6) 0.0420(18) Uani 1 1 d . . . . .
H9B H 0.3464 -1.1068 0.8379 0.050 Uiso 1 1 calc R U . . .
C10B C 0.3512(17) -1.2401(13) 0.5042(6) 0.059(3) Uani 1 1 d . . . . .
C11B C 0.2153(14) -1.4047(12) 0.4626(6) 0.0491(19) Uani 1 1 d . . . . .
H11B H 0.0988 -1.3774 0.4224 0.059 Uiso 1 1 calc R U . . .
C12B C 0.3280(16) -1.5011(15) 0.4014(7) 0.063(2) Uani 1 1 d . . . . .
H12C H 0.4445 -1.5279 0.4404 0.076 Uiso 1 1 calc R U . . .
H12D H 0.2418 -1.6057 0.3764 0.076 Uiso 1 1 calc R U . . .
C13B C 0.3945(19) -1.4069(15) 0.3218(8) 0.079(3) Uani 1 1 d . . . . .
H13B H 0.4854 -1.4653 0.2942 0.095 Uiso 1 1 calc R U . . .
H13C H 0.4682 -1.2972 0.3462 0.095 Uiso 1 1 calc R U . . .
C14B C 0.149(2) -1.5749(18) 0.1678(9) 0.096(4) Uani 1 1 d . . . . .
H14D H 0.2023 -1.5621 0.1105 0.143 Uiso 1 1 calc R U . . .
H14E H 0.0080 -1.6174 0.1538 0.143 Uiso 1 1 calc R U . . .
H14F H 0.2140 -1.6517 0.2043 0.143 Uiso 1 1 calc R U . . .
 
 
_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 1.414(7) . ?
S1A O5A 1.416(8) . ?
S1A N1A 1.668(8) . ?
S1A C7A 1.734(9) . ?
O1A C1A 1.252(12) . ?
O2A C1A 1.311(12) . ?
O2A H1 0.86(2) . ?
O3A C10A 1.268(13) . ?
O4A C10A 1.304(13) . ?
O4A H2 0.85(2) . ?
N1A C11A 1.440(14) . ?
N1A H3 0.85(2) . ?
C1A C2A 1.480(13) . ?
C2A C3A 1.534(11) . ?
C2A C3B 1.594(13) . ?
C2A H2A 0.9800 . ?
C3A C4A 1.512(11) . ?
C3A C2B 1.596(11) . ?
C3A H3A 0.9800 . ?
C4A C5A 1.377(11) . ?
C4A C9A 1.402(11) . ?
C5A C6A 1.399(12) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.376(11) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.383(11) . ?
C8A C9A 1.378(13) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.486(14) . ?
C11A C12A 1.550(14) . ?
C11A H11A 0.9800 . ?
C12A C13A 1.523(18) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C14A 1.47(3) . ?
C13A C15A 1.53(2) . ?
C13A H13A 0.9800 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
S1B O5B 1.410(9) . ?
S1B O6B 1.446(8) . ?
S1B N1B 1.603(8) . ?
S1B C7B 1.790(8) . ?
S2B C14B 1.745(13) . ?
S2B C13B 1.812(14) . ?
O1B C1B 1.256(12) . ?
O2B C1B 1.281(12) . ?
O2B H4 0.85(2) . ?
O3B C10B 1.218(12) . ?
O4B C10B 1.268(12) . ?
O4B H5 0.84(2) . ?
N1B C11B 1.445(12) . ?
N1B H6 0.84(2) . ?
C1B C2B 1.462(13) . ?
C2B C3B 1.535(12) . ?
C2B H2B 0.9800 . ?
C3B C4B 1.527(13) . ?
C3B H3B 0.9800 . ?
C4B C5B 1.384(12) . ?
C4B C9B 1.396(12) . ?
C5B C6B 1.373(13) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.401(12) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.363(13) . ?
C8B C9B 1.385(12) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C10B C11B 1.535(14) . ?
C11B C12B 1.539(13) . ?
C11B H11B 0.9800 . ?
C12B C13B 1.499(16) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B H13B 0.9700 . ?
C13B H13C 0.9700 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 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 121.6(5) . . ?
O6A S1A N1A 103.7(5) . . ?
O5A S1A N1A 105.6(5) . . ?
O6A S1A C7A 109.0(4) . . ?
O5A S1A C7A 109.3(4) . . ?
N1A S1A C7A 106.4(4) . . ?
C1A O2A H1 119(9) . . ?
C10A O4A H2 108(9) . . ?
C11A N1A S1A 122.0(6) . . ?
C11A N1A H3 121(8) . . ?
S1A N1A H3 101(7) . . ?
O1A C1A O2A 123.1(9) . . ?
O1A C1A C2A 121.6(8) . . ?
O2A C1A C2A 114.7(9) . . ?
C1A C2A C3A 116.4(7) . . ?
C1A C2A C3B 112.2(7) . . ?
C3A C2A C3B 89.8(6) . . ?
C1A C2A H2A 112.2 . . ?
C3A C2A H2A 112.2 . . ?
C3B C2A H2A 112.2 . . ?
C4A C3A C2A 120.8(6) . . ?
C4A C3A C2B 116.3(6) . . ?
C2A C3A C2B 90.1(6) . . ?
C4A C3A H3A 109.3 . . ?
C2A C3A H3A 109.3 . . ?
C2B C3A H3A 109.3 . . ?
C5A C4A C9A 118.3(7) . . ?
C5A C4A C3A 117.6(6) . . ?
C9A C4A C3A 123.9(7) . . ?
C4A C5A C6A 121.6(7) . . ?
C4A C5A H5A 119.2 . . ?
C6A C5A H5A 119.2 . . ?
C7A C6A C5A 118.7(7) . . ?
C7A C6A H6A 120.6 . . ?
C5A C6A H6A 120.6 . . ?
C6A C7A C8A 120.6(7) . . ?
C6A C7A S1A 118.8(6) . . ?
C8A C7A S1A 120.4(6) . . ?
C9A C8A C7A 120.2(7) . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C8A C9A C4A 120.4(7) . . ?
C8A C9A H9A 119.8 . . ?
C4A C9A H9A 119.8 . . ?
O3A C10A O4A 124.5(9) . . ?
O3A C10A C11A 120.4(10) . . ?
O4A C10A C11A 115.1(9) . . ?
N1A C11A C10A 115.4(8) . . ?
N1A C11A C12A 109.6(9) . . ?
C10A C11A C12A 105.8(9) . . ?
N1A C11A H11A 108.6 . . ?
C10A C11A H11A 108.6 . . ?
C12A C11A H11A 108.6 . . ?
C13A C12A C11A 116.3(12) . . ?
C13A C12A H12A 108.2 . . ?
C11A C12A H12A 108.2 . . ?
C13A C12A H12B 108.2 . . ?
C11A C12A H12B 108.2 . . ?
H12A C12A H12B 107.4 . . ?
C14A C13A C12A 115.3(15) . . ?
C14A C13A C15A 112.5(15) . . ?
C12A C13A C15A 110.9(15) . . ?
C14A C13A H13A 105.8 . . ?
C12A C13A H13A 105.8 . . ?
C15A C13A H13A 105.8 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O5B S1B O6B 121.4(5) . . ?
O5B S1B N1B 108.2(5) . . ?
O6B S1B N1B 104.9(4) . . ?
O5B S1B C7B 106.6(4) . . ?
O6B S1B C7B 107.9(4) . . ?
N1B S1B C7B 107.0(4) . . ?
C14B S2B C13B 100.5(7) . . ?
C1B O2B H4 122(9) . . ?
C10B O4B H5 119(9) . . ?
C11B N1B S1B 122.5(7) . . ?
C11B N1B H6 105(7) . . ?
S1B N1B H6 132(7) . . ?
O1B C1B O2B 124.6(9) . . ?
O1B C1B C2B 120.4(8) . . ?
O2B C1B C2B 114.6(9) . . ?
C1B C2B C3B 116.9(7) . . ?
C1B C2B C3A 112.1(6) . . ?
C3B C2B C3A 89.7(6) . . ?
C1B C2B H2B 112.1 . . ?
C3B C2B H2B 112.1 . . ?
C3A C2B H2B 112.1 . . ?
C4B C3B C2B 120.9(7) . . ?
C4B C3B C2A 114.4(8) . . ?
C2B C3B C2A 90.2(6) . . ?
C4B C3B H3B 110.0 . . ?
C2B C3B H3B 110.0 . . ?
C2A C3B H3B 110.0 . . ?
C5B C4B C9B 118.4(8) . . ?
C5B C4B C3B 118.9(8) . . ?
C9B C4B C3B 122.6(8) . . ?
C6B C5B C4B 121.2(8) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C5B C6B C7B 119.2(8) . . ?
C5B C6B H6B 120.4 . . ?
C7B C6B H6B 120.4 . . ?
C8B C7B C6B 120.2(8) . . ?
C8B C7B S1B 121.4(7) . . ?
C6B C7B S1B 118.3(7) . . ?
C7B C8B C9B 120.0(8) . . ?
C7B C8B H8B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C8B C9B C4B 120.5(8) . . ?
C8B C9B H9B 119.8 . . ?
C4B C9B H9B 119.8 . . ?
O3B C10B O4B 125.7(10) . . ?
O3B C10B C11B 119.4(9) . . ?
O4B C10B C11B 114.9(9) . . ?
N1B C11B C10B 113.5(7) . . ?
N1B C11B C12B 109.4(8) . . ?
C10B C11B C12B 109.5(8) . . ?
N1B C11B H11B 108.1 . . ?
C10B C11B H11B 108.1 . . ?
C12B C11B H11B 108.1 . . ?
C13B C12B C11B 113.7(9) . . ?
C13B C12B H12C 108.8 . . ?
C11B C12B H12C 108.8 . . ?
C13B C12B H12D 108.8 . . ?
C11B C12B H12D 108.8 . . ?
H12C C12B H12D 107.7 . . ?
C12B C13B S2B 114.1(8) . . ?
C12B C13B H13B 108.7 . . ?
S2B C13B H13B 108.7 . . ?
C12B C13B H13C 108.7 . . ?
S2B C13B H13C 108.7 . . ?
H13B C13B H13C 107.6 . . ?
S2B C14B H14D 109.5 . . ?
S2B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
S2B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 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 174.0(8) . . . . ?
O5A S1A N1A C11A -57.0(8) . . . . ?
C7A S1A N1A C11A 59.1(8) . . . . ?
O1A C1A C2A C3A 30.0(12) . . . . ?
O2A C1A C2A C3A -158.5(8) . . . . ?
O1A C1A C2A C3B -71.5(10) . . . . ?
O2A C1A C2A C3B 100.0(9) . . . . ?
C1A C2A C3A C4A 126.5(8) . . . . ?
C3B C2A C3A C4A -118.6(7) . . . . ?
C1A C2A C3A C2B -112.3(7) . . . . ?
C3B C2A C3A C2B 2.6(7) . . . . ?
C2A C3A C4A C5A -176.4(7) . . . . ?
C2B C3A C4A C5A 76.3(8) . . . . ?
C2A C3A C4A C9A 8.3(11) . . . . ?
C2B C3A C4A C9A -99.1(9) . . . . ?
C9A C4A C5A C6A 5.2(11) . . . . ?
C3A C4A C5A C6A -170.5(7) . . . . ?
C4A C5A C6A C7A -2.5(12) . . . . ?
C5A C6A C7A C8A -1.4(12) . . . . ?
C5A C6A C7A S1A 173.0(6) . . . . ?
O6A S1A C7A C6A 155.4(7) . . . . ?
O5A S1A C7A C6A 20.4(8) . . . . ?
N1A S1A C7A C6A -93.3(7) . . . . ?
O6A S1A C7A C8A -30.1(8) . . . . ?
O5A S1A C7A C8A -165.1(7) . . . . ?
N1A S1A C7A C8A 81.2(7) . . . . ?
C6A C7A C8A C9A 2.6(12) . . . . ?
S1A C7A C8A C9A -171.8(7) . . . . ?
C7A C8A C9A C4A 0.1(12) . . . . ?
C5A C4A C9A C8A -3.9(11) . . . . ?
C3A C4A C9A C8A 171.4(7) . . . . ?
S1A N1A C11A C10A -76.8(10) . . . . ?
S1A N1A C11A C12A 164.0(8) . . . . ?
O3A C10A C11A N1A 145.0(9) . . . . ?
O4A C10A C11A N1A -33.9(12) . . . . ?
O3A C10A C11A C12A -93.7(12) . . . . ?
O4A C10A C11A C12A 87.5(10) . . . . ?
N1A C11A C12A C13A -75.2(14) . . . . ?
C10A C11A C12A C13A 159.7(12) . . . . ?
C11A C12A C13A C14A -62(2) . . . . ?
C11A C12A C13A C15A 168.5(14) . . . . ?
O5B S1B N1B C11B 50.2(8) . . . . ?
O6B S1B N1B C11B -178.9(7) . . . . ?
C7B S1B N1B C11B -64.4(8) . . . . ?
O1B C1B C2B C3B -26.4(12) . . . . ?
O2B C1B C2B C3B 160.8(8) . . . . ?
O1B C1B C2B C3A 75.2(10) . . . . ?
O2B C1B C2B C3A -97.7(9) . . . . ?
C4A C3A C2B C1B 3.1(9) . . . . ?
C2A C3A C2B C1B -121.9(7) . . . . ?
C4A C3A C2B C3B 122.2(6) . . . . ?
C2A C3A C2B C3B -2.7(8) . . . . ?
C1B C2B C3B C4B -123.7(9) . . . . ?
C3A C2B C3B C4B 121.5(8) . . . . ?
C1B C2B C3B C2A 117.5(8) . . . . ?
C3A C2B C3B C2A 2.6(7) . . . . ?
C1A C2A C3B C4B -8.5(10) . . . . ?
C3A C2A C3B C4B -127.1(7) . . . . ?
C1A C2A C3B C2B 115.9(7) . . . . ?
C3A C2A C3B C2B -2.7(8) . . . . ?
C2B C3B C4B C5B -177.7(8) . . . . ?
C2A C3B C4B C5B -71.7(10) . . . . ?
C2B C3B C4B C9B 0.0(13) . . . . ?
C2A C3B C4B C9B 105.9(9) . . . . ?
C9B C4B C5B C6B -5.5(13) . . . . ?
C3B C4B C5B C6B 172.3(9) . . . . ?
C4B C5B C6B C7B 0.5(14) . . . . ?
C5B C6B C7B C8B 5.1(13) . . . . ?
C5B C6B C7B S1B -170.9(7) . . . . ?
O5B S1B C7B C8B 164.9(7) . . . . ?
O6B S1B C7B C8B 33.0(8) . . . . ?
N1B S1B C7B C8B -79.5(7) . . . . ?
O5B S1B C7B C6B -19.2(8) . . . . ?
O6B S1B C7B C6B -151.1(7) . . . . ?
N1B S1B C7B C6B 96.5(7) . . . . ?
C6B C7B C8B C9B -5.5(12) . . . . ?
S1B C7B C8B C9B 170.3(6) . . . . ?
C7B C8B C9B C4B 0.4(11) . . . . ?
C5B C4B C9B C8B 5.0(12) . . . . ?
C3B C4B C9B C8B -172.6(8) . . . . ?
S1B N1B C11B C10B 77.6(9) . . . . ?
S1B N1B C11B C12B -159.8(7) . . . . ?
O3B C10B C11B N1B -143.4(10) . . . . ?
O4B C10B C11B N1B 36.3(11) . . . . ?
O3B C10B C11B C12B 94.1(11) . . . . ?
O4B C10B C11B C12B -86.2(10) . . . . ?
N1B C11B C12B C13B 175.5(8) . . . . ?
C10B C11B C12B C13B -59.6(11) . . . . ?
C11B C12B C13B S2B -69.3(11) . . . . ?
C14B S2B C13B C12B -81.4(9) . . . . ?
 
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 
O4B H5 O1A  0.84(2) 1.92(5) 2.687(10) 151(8) .
O2A H1 O3B  0.86(2) 2.05(10) 2.716(10) 134(12) .
O4A H2 O1B  0.85(2) 1.83(3) 2.675(11) 174(13) .
O2B H4 O3A  0.85(2) 1.87(6) 2.666(12) 154(12) .
N1A H3 O2B  0.85(2) 2.62(8) 3.248(10) 131(9) 1_565
N1B H6 O2A  0.84(2) 2.56(3) 3.397(11) 171(9) 1_545
 
_refine_diff_density_max    0.674
_refine_diff_density_min   -0.395
_refine_diff_density_rms    0.116

_shelxl_version_number 2013-4



#==END

 
data_kaw95 

# L-3 unreacted
 
# start Validation Reply Form
_vrf_PLAT242_kw91
;
PROBLEM: Low Ueq as Compared to Neighbors for .....        C13 Check 
RESPONSE: Low Ueq issue are the result of UV illumination
of the crystal.
;
_vrf_PLAT340_kw91
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0172 Ang.  
RESPONSE: Low bond precision is the result of 
UV exposure of the crystal.
;
# end Validation Reply Form


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_absolute_configuration  rm
_chemical_formula_moiety          
 'C15 H19 N O6 S' 
_chemical_formula_sum 
 'C15 H19 N O6 S' 
_chemical_formula_weight          341.37 
 
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' 
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    7.7603(1) 
_cell_length_b                    6.9346(1) 
_cell_length_c                    15.1225(1) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.392(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      812.385(17) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     8135
_cell_measurement_theta_min       2.819
_cell_measurement_theta_max       71.557
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'colorless'
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.33 
_exptl_crystal_size_min           0.11 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.396 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              360 
_exptl_absorpt_coefficient_mu     2.050 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.4951 
_exptl_absorpt_correction_T_max   0.8029 
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11646 
_diffrn_reflns_av_R_equivalents   0.0249 
_diffrn_reflns_av_sigmaI/netI     0.0300 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.927
_diffrn_reflns_theta_max          68.212
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.962
_diffrn_reflns_point_group_measured_fraction_full  0.965
_reflns_number_total              2871
_reflns_number_gt                 2819
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.773
_reflns_Friedel_fraction_max      0.921
_reflns_Friedel_fraction_full     0.926
 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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 a difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with O/N-H bond distances
 of 0.85(2) angstroms.
; 
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+0.1182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.047(5)
_refine_ls_number_reflns          2871
_refine_ls_number_parameters      219
_refine_ls_number_restraints      4
_refine_ls_R_factor_all           0.0249
_refine_ls_R_factor_gt            0.0245
_refine_ls_wR_factor_ref          0.0641
_refine_ls_wR_factor_gt           0.0637
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.27772(6) 0.36955(7) 0.75035(3) 0.02114(14) Uani 1 1 d . . . . .
O1 O -0.67729(19) 0.2883(2) 0.41207(9) 0.0260(4) Uani 1 1 d D . . . .
H20 H -0.764(3) 0.276(4) 0.3790(16) 0.031 Uiso 1 1 d D U . . .
O2 O -0.54066(18) 0.3232(2) 0.28651(9) 0.0244(3) Uani 1 1 d . . . . .
O3 O -0.18816(18) 0.7185(3) 0.81557(10) 0.0284(4) Uani 1 1 d D . . . .
H21 H -0.275(3) 0.752(5) 0.7817(17) 0.034 Uiso 1 1 d D U . . .
O4 O -0.03380(17) 0.7561(2) 0.69624(9) 0.0225(3) Uani 1 1 d . . . . .
O5 O 0.2640(2) 0.2403(3) 0.82321(10) 0.0294(4) Uani 1 1 d . . . . .
O6 O 0.42982(17) 0.3728(3) 0.70115(9) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.2556(2) 0.5863(3) 0.78710(11) 0.0194(4) Uani 1 1 d D . . . .
H22 H 0.310(3) 0.671(4) 0.7633(16) 0.023 Uiso 1 1 d D U . . .
C1 C -0.5377(3) 0.3125(3) 0.36765(13) 0.0214(4) Uani 1 1 d . . . . .
C2 C -0.3742(3) 0.3256(3) 0.42141(14) 0.0245(5) Uani 1 1 d . . . . .
H2 H -0.2724 0.3556 0.3923 0.029 Uiso 1 1 calc R U . . .
C3 C -0.3605(3) 0.2979(3) 0.50880(14) 0.0229(4) Uani 1 1 d . . . . .
H3 H -0.4638 0.2716 0.5373 0.027 Uiso 1 1 calc R U . . .
C4 C -0.1994(3) 0.3047(3) 0.56452(14) 0.0218(4) Uani 1 1 d . . . . .
C5 C -0.0434(2) 0.3681(4) 0.53223(12) 0.0238(4) Uani 1 1 d . . . . .
H5 H -0.0391 0.4029 0.4716 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1040(2) 0.3803(4) 0.58783(13) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.2091 0.4249 0.5660 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0969(3) 0.3266(3) 0.67623(13) 0.0205(4) Uani 1 1 d . . . . .
C8 C -0.0544(3) 0.2575(3) 0.70912(14) 0.0215(4) Uani 1 1 d . . . . .
H8 H -0.0565 0.2170 0.7691 0.026 Uiso 1 1 calc R U . . .
C9 C -0.2025(3) 0.2482(3) 0.65335(14) 0.0226(4) Uani 1 1 d . . . . .
H9 H -0.3071 0.2031 0.6756 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0455(3) 0.7104(3) 0.77330(13) 0.0189(4) Uani 1 1 d . . . . .
C11 C 0.1057(3) 0.6417(3) 0.83458(13) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.0670 0.5266 0.8679 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1517(3) 0.8026(3) 0.90171(14) 0.0240(5) Uani 1 1 d . . . . .
H12A H 0.1851 0.9189 0.8688 0.029 Uiso 1 1 calc R U . . .
H12B H 0.0471 0.8352 0.9330 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2977(3) 0.7542(3) 0.97093(13) 0.0235(5) Uani 1 1 d . . . . .
H13 H 0.4063 0.7330 0.9398 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3232(3) 0.9274(4) 1.03248(18) 0.0373(6) Uani 1 1 d . . . . .
H14A H 0.2217 0.9425 1.0674 0.056 Uiso 1 1 calc R U . . .
H14B H 0.3386 1.0440 0.9972 0.056 Uiso 1 1 calc R U . . .
H14C H 0.4258 0.9070 1.0724 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2600(3) 0.5736(4) 1.02389(15) 0.0339(6) Uani 1 1 d . . . . .
H15A H 0.3524 0.5541 1.0701 0.051 Uiso 1 1 calc R U . . .
H15B H 0.2538 0.4617 0.9843 0.051 Uiso 1 1 calc R U . . .
H15C H 0.1497 0.5890 1.0514 0.051 Uiso 1 1 calc R U . . .
 
 
_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 O5 1.4291(18) . ?
S1 O6 1.4321(14) . ?
S1 N1 1.6150(19) . ?
S1 C7 1.769(2) . ?
O1 C1 1.319(2) . ?
O1 H20 0.82(2) . ?
O2 C1 1.228(2) . ?
O3 C10 1.312(2) . ?
O3 H21 0.85(2) . ?
O4 C10 1.216(2) . ?
N1 C11 1.454(3) . ?
N1 H22 0.82(2) . ?
C1 C2 1.469(3) . ?
C2 C3 1.333(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.467(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.401(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.528(3) . ?
C11 C12 1.536(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.533(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.524(3) . ?
C13 C14 1.525(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O5 S1 O6 120.78(10) . . ?
O5 S1 N1 107.68(10) . . ?
O6 S1 N1 105.77(10) . . ?
O5 S1 C7 106.89(10) . . ?
O6 S1 C7 108.72(9) . . ?
N1 S1 C7 106.14(9) . . ?
C1 O1 H20 111.8(19) . . ?
C10 O3 H21 112.3(19) . . ?
C11 N1 S1 121.36(15) . . ?
C11 N1 H22 118(2) . . ?
S1 N1 H22 116.7(19) . . ?
O2 C1 O1 123.34(18) . . ?
O2 C1 C2 120.89(18) . . ?
O1 C1 C2 115.77(17) . . ?
C3 C2 C1 123.70(19) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 125.4(2) . . ?
C2 C3 H3 117.3 . . ?
C4 C3 H3 117.3 . . ?
C9 C4 C5 119.03(18) . . ?
C9 C4 C3 118.68(19) . . ?
C5 C4 C3 122.28(19) . . ?
C6 C5 C4 120.54(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.30(18) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 121.29(18) . . ?
C8 C7 S1 119.18(15) . . ?
C6 C7 S1 119.24(16) . . ?
C9 C8 C7 119.11(18) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 120.68(19) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
O4 C10 O3 124.67(18) . . ?
O4 C10 C11 124.33(17) . . ?
O3 C10 C11 110.97(16) . . ?
N1 C11 C10 113.02(16) . . ?
N1 C11 C12 110.92(16) . . ?
C10 C11 C12 108.32(17) . . ?
N1 C11 H11 108.1 . . ?
C10 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C13 C12 C11 115.18(18) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C15 C13 C14 110.39(19) . . ?
C15 C13 C12 112.45(18) . . ?
C14 C13 C12 107.95(19) . . ?
C15 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
C12 C13 H13 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O5 S1 N1 C11 -54.59(17) . . . . ?
O6 S1 N1 C11 175.00(15) . . . . ?
C7 S1 N1 C11 59.60(17) . . . . ?
O2 C1 C2 C3 -173.8(2) . . . . ?
O1 C1 C2 C3 6.0(3) . . . . ?
C1 C2 C3 C4 178.3(2) . . . . ?
C2 C3 C4 C9 -171.9(2) . . . . ?
C2 C3 C4 C5 9.0(4) . . . . ?
C9 C4 C5 C6 -2.0(4) . . . . ?
C3 C4 C5 C6 177.2(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 S1 -172.41(19) . . . . ?
O5 S1 C7 C8 27.9(2) . . . . ?
O6 S1 C7 C8 159.82(18) . . . . ?
N1 S1 C7 C8 -86.80(19) . . . . ?
O5 S1 C7 C6 -158.22(18) . . . . ?
O6 S1 C7 C6 -26.3(2) . . . . ?
N1 S1 C7 C6 87.05(19) . . . . ?
C6 C7 C8 C9 -2.2(3) . . . . ?
S1 C7 C8 C9 171.48(17) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C5 C4 C9 C8 1.0(3) . . . . ?
C3 C4 C9 C8 -178.1(2) . . . . ?
S1 N1 C11 C10 -87.9(2) . . . . ?
S1 N1 C11 C12 150.20(15) . . . . ?
O4 C10 C11 N1 -15.6(3) . . . . ?
O3 C10 C11 N1 166.18(19) . . . . ?
O4 C10 C11 C12 107.8(2) . . . . ?
O3 C10 C11 C12 -70.5(2) . . . . ?
N1 C11 C12 C13 -57.6(2) . . . . ?
C10 C11 C12 C13 177.80(17) . . . . ?
C11 C12 C13 C15 -56.9(2) . . . . ?
C11 C12 C13 C14 -178.97(19) . . . . ?
 
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 H20 O4  0.82(2) 1.89(2) 2.7065(19) 178(3) 2_446
O3 H21 O2  0.85(2) 1.78(2) 2.637(2) 179(3) 2_456
N1 H22 O2  0.82(2) 2.24(2) 3.021(2) 158(3) 2_556
 
_refine_diff_density_max    0.234
_refine_diff_density_min   -0.269
_refine_diff_density_rms    0.044

_shelxl_version_number 2013-4



#==END

 
data_kw91
# L-3 UV irradiated 4 hours
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C15.42 H18.58 N O6 S' 
_chemical_formula_sum
 'C15.42 H18.58 N O6 S' 
_chemical_formula_weight          346.10

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    7.8661(4)
_cell_length_b                    7.1700(4)
_cell_length_c                    14.9612(8)
_cell_angle_alpha                 90
_cell_angle_beta                  91.665(4)
_cell_angle_gamma                 90
_cell_volume                      843.45(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2110
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       25.555
 
_exptl_crystal_description        'transparent plate'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?           
_exptl_crystal_density_diffrn     1.363          
_exptl_crystal_F_000              364
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.33
_exptl_crystal_size_min           0.11
_exptl_absorpt_coefficient_mu     0.222
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.916 
_exptl_absorpt_correction_T_max   0.976 
_exptl_absorpt_process_details    
        'SADABS (Bruker, 2010)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'Bruker P4 with Apex II CCD'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  8.33
_diffrn_reflns_number             7978
_diffrn_reflns_av_unetI/netI      0.0770
_diffrn_reflns_av_R_equivalents   0.0556
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          1.362
_diffrn_reflns_theta_max          25.350
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3084
_reflns_number_gt                 1369
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.838
_reflns_Friedel_fraction_max      0.999
_reflns_Friedel_fraction_full     1.000
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Apex2'
_computing_cell_refinement        'Apex2'
_computing_data_reduction         
'Saint (Bruker, 2011) and XPREP (Bruker, 2009)'
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material     'XSEED (Barbour, 2001)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1044P)²+0.2146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.07(7)
_chemical_absolute_configuration  rmad
_refine_ls_number_reflns          3084
_refine_ls_number_parameters      239
_refine_ls_number_restraints      17
_refine_ls_R_factor_all           0.1746
_refine_ls_R_factor_gt            0.0728
_refine_ls_wR_factor_ref          0.2291
_refine_ls_wR_factor_gt           0.1787
_refine_ls_goodness_of_fit_ref    1.008
_refine_ls_restrained_S_all       1.006
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.7309(4) 0.5180(5) 0.2492(3) 0.1093(13) Uani 1 1 d D . . . .
O1 O -0.1794(10) 0.4630(13) -0.0915(5) 0.106(3) Uani 1 1 d D . . . .
O2 O -0.0335(8) 0.4601(16) -0.2150(5) 0.122(3) Uani 1 1 d D . . . .
O3 O 0.3022(9) 0.8801(13) 0.3153(5) 0.108(3) Uani 1 1 d D . . . .
O4 O 0.4598(8) 0.9223(12) 0.1970(5) 0.102(3) Uani 1 1 d D . . . .
O5 O 0.7014(11) 0.4055(13) 0.3254(7) 0.134(3) Uani 1 1 d . . . . .
O6 O 0.8834(9) 0.4974(18) 0.2010(6) 0.176(5) Uani 1 1 d . . . . .
N1 N 0.7280(9) 0.7286(15) 0.2822(6) 0.089(3) Uani 1 1 d D . . . .
C1 C -0.0414(14) 0.4726(18) -0.1378(10) 0.101(4) Uani 1 1 d . . . A 1
C2 C 0.1243(18) 0.492(3) -0.0829(10) 0.097(5) Uani 0.789(19) 1 d . . P A 1
H2 H 0.2242 0.5225 -0.1112 0.117 Uiso 0.789(19) 1 calc R U P A 1
C3 C 0.1268(17) 0.466(2) 0.0038(10) 0.092(5) Uani 0.789(19) 1 d . . P A 1
H3 H 0.0235 0.4405 0.0299 0.111 Uiso 0.789(19) 1 calc R U P A 1
C4 C 0.2793(15) 0.475(2) 0.0642(8) 0.113(5) Uani 1 1 d . . . . .
C5 C 0.2619(14) 0.430(2) 0.1528(9) 0.111(4) Uani 1 1 d . . . . .
H5 H 0.1570 0.3959 0.1748 0.133 Uiso 1 1 calc R U . . .
C6 C 0.4052(14) 0.4372(18) 0.2079(8) 0.103(4) Uani 1 1 d . . . . .
H6 H 0.3988 0.4041 0.2678 0.124 Uiso 1 1 calc R U . . .
C7 C 0.5536(13) 0.4919(19) 0.1751(8) 0.097(4) Uani 1 1 d . . . . .
C8 C 0.5712(15) 0.540(3) 0.0885(8) 0.131(6) Uani 1 1 d . . . . .
H8 H 0.6755 0.5807 0.0681 0.157 Uiso 1 1 calc R U . . .
C9 C 0.4355(18) 0.529(3) 0.0331(9) 0.149(6) Uani 1 1 d . . . . .
H9 H 0.4462 0.5575 -0.0271 0.179 Uiso 1 1 calc R U . . .
C10 C 0.4424(12) 0.8744(16) 0.2738(8) 0.079(3) Uani 1 1 d . . . . .
C11 C 0.5954(11) 0.8036(14) 0.3324(6) 0.070(3) Uani 1 1 d D . . . .
H11 H 0.5536 0.7043 0.3710 0.084 Uiso 1 1 calc R U . . .
C12 C 0.6536(13) 0.9587(17) 0.3906(7) 0.097(4) Uani 1 1 d . . . . .
H12A H 0.5554 1.0100 0.4198 0.116 Uiso 1 1 calc R U . . .
H12B H 0.6990 1.0561 0.3531 0.116 Uiso 1 1 calc R U . . .
C13 C 0.7875(13) 0.9102(17) 0.4623(8) 0.093(3) Uani 1 1 d . . . . .
H13 H 0.8880 0.8601 0.4334 0.111 Uiso 1 1 calc R U . . .
C14 C 0.839(2) 1.087(3) 0.5147(12) 0.190(8) Uani 1 1 d . . . . .
H14A H 0.7415 1.1352 0.5444 0.286 Uiso 1 1 calc R U . . .
H14B H 0.8803 1.1788 0.4742 0.286 Uiso 1 1 calc R U . . .
H14C H 0.9264 1.0565 0.5583 0.286 Uiso 1 1 calc R U . . .
C15 C 0.7195(18) 0.765(3) 0.5242(8) 0.149(6) Uani 1 1 d . . . . .
H15A H 0.6191 0.8117 0.5515 0.223 Uiso 1 1 calc R U . . .
H15B H 0.8040 0.7368 0.5698 0.223 Uiso 1 1 calc R U . . .
H15C H 0.6921 0.6541 0.4910 0.223 Uiso 1 1 calc R U . . .
C2A C 0.037(7) 0.275(7) -0.055(4) 0.13(3) Uiso 0.211(19) 1 d D . P A 2
C3A C 0.019(8) 0.319(10) 0.048(4) 0.12(2) Uiso 0.211(19) 1 d D . P A 2
C2B C -0.051(9) 0.116(10) 0.068(5) 0.16(3) Uiso 0.211(19) 1 d D . P A 2
C3B C -0.034(7) 0.071(8) -0.035(4) 0.11(2) Uiso 0.211(19) 1 d D . P A 2
H21 H 0.223(4) 0.926(12) 0.282(3) 0.18(6) Uiso 1 1 d D . . . .
H20 H -0.267(3) 0.461(14) -0.1261(19) 0.20(7) Uiso 1 1 d D . . . .
H22 H 0.795(10) 0.802(4) 0.256(6) 0.13(5) Uiso 1 1 d D . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O5 1.420(11) . ?
S1 O6 1.425(8) . ?
S1 N1 1.589(10) . ?
S1 C7 1.766(10) . ?
O1 C1 1.306(12) . ?
O1 H20 0.849(15) . ?
O2 C1 1.162(12) . ?
O3 C10 1.282(11) . ?
O3 H21 0.854(15) . ?
O4 C10 1.211(11) . ?
N1 C11 1.409(11) . ?
N1 H22 0.849(13) . ?
C1 C2 1.526(18) . ?
C2 C3 1.310(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.482(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(16) . ?
C4 C9 1.381(15) . ?
C5 C6 1.378(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.338(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.352(15) . ?
C8 C9 1.336(16) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.553(13) . ?
C11 C12 1.477(14) . ?
C11 H11 0.9800 . ?
C12 C13 1.521(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.502(17) . ?
C13 C14 1.54(2) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2A C3B 1.59(5) . ?
C2A C3A 1.60(5) . ?
C3A C2B 1.59(5) . ?
C3A C3B 1.82(10) 2 ?
C2B C3B 1.59(5) . ?
C3B C3A 1.82(10) 2_545 ?
 
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
O5 S1 O6 120.5(6) . . ?
O5 S1 N1 106.6(5) . . ?
O6 S1 N1 106.0(6) . . ?
O5 S1 C7 107.4(6) . . ?
O6 S1 C7 109.4(6) . . ?
N1 S1 C7 106.1(5) . . ?
C1 O1 H20 110(2) . . ?
C10 O3 H21 111(2) . . ?
C11 N1 S1 123.1(8) . . ?
C11 N1 H22 119(3) . . ?
S1 N1 H22 115(2) . . ?
O2 C1 O1 126.3(10) . . ?
O2 C1 C2 118.2(11) . . ?
O1 C1 C2 115.4(12) . . ?
C3 C2 C1 120.6(13) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 125.9(13) . . ?
C2 C3 H3 117.0 . . ?
C4 C3 H3 117.0 . . ?
C5 C4 C9 120.3(11) . . ?
C5 C4 C3 118.5(12) . . ?
C9 C4 C3 121.2(13) . . ?
C4 C5 C6 117.7(11) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 120.0(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 122.7(10) . . ?
C6 C7 S1 118.9(9) . . ?
C8 C7 S1 118.2(10) . . ?
C9 C8 C7 118.5(12) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C4 120.7(13) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
O4 C10 O3 124.9(9) . . ?
O4 C10 C11 121.4(9) . . ?
O3 C10 C11 113.6(9) . . ?
N1 C11 C12 112.3(8) . . ?
N1 C11 C10 113.5(8) . . ?
C12 C11 C10 108.0(8) . . ?
N1 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C10 C11 H11 107.6 . . ?
C11 C12 C13 116.1(9) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C15 C13 C12 110.0(10) . . ?
C15 C13 C14 110.4(12) . . ?
C12 C13 C14 109.7(12) . . ?
C15 C13 H13 108.9 . . ?
C12 C13 H13 108.9 . . ?
C14 C13 H13 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3B C2A C3A 87(4) . . ?
C2B C3A C2A 92(4) . . ?
C2B C3A C3B 162(4) . 2 ?
C2A C3A C3B 95(4) . 2 ?
C3A C2B C3B 88(4) . . ?
C2B C3B C2A 92(4) . . ?
C2B C3B C3A 108(4) . 2_545 ?
C2A C3B C3A 150(4) . 2_545 ?
 
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
O5 S1 N1 C11 -50.9(9) . . . . ?
O6 S1 N1 C11 179.6(8) . . . . ?
C7 S1 N1 C11 63.4(9) . . . . ?
O2 C1 C2 C3 -165.2(15) . . . . ?
O1 C1 C2 C3 12(2) . . . . ?
C1 C2 C3 C4 177.8(14) . . . . ?
C2 C3 C4 C5 -174.9(16) . . . . ?
C2 C3 C4 C9 6(3) . . . . ?
C9 C4 C5 C6 -1(2) . . . . ?
C3 C4 C5 C6 179.5(13) . . . . ?
C4 C5 C6 C7 1.9(19) . . . . ?
C5 C6 C7 C8 -1(2) . . . . ?
C5 C6 C7 S1 174.9(10) . . . . ?
O5 S1 C7 C6 23.1(12) . . . . ?
O6 S1 C7 C6 155.4(11) . . . . ?
N1 S1 C7 C6 -90.7(11) . . . . ?
O5 S1 C7 C8 -161.3(12) . . . . ?
O6 S1 C7 C8 -29.0(15) . . . . ?
N1 S1 C7 C8 84.9(12) . . . . ?
C6 C7 C8 C9 -2(3) . . . . ?
S1 C7 C8 C9 -177.0(13) . . . . ?
C7 C8 C9 C4 2(3) . . . . ?
C5 C4 C9 C8 -1(3) . . . . ?
C3 C4 C9 C8 178.4(17) . . . . ?
S1 N1 C11 C12 152.0(8) . . . . ?
S1 N1 C11 C10 -85.2(10) . . . . ?
O4 C10 C11 N1 -24.9(15) . . . . ?
O3 C10 C11 N1 156.5(9) . . . . ?
O4 C10 C11 C12 100.2(12) . . . . ?
O3 C10 C11 C12 -78.3(11) . . . . ?
N1 C11 C12 C13 -62.2(12) . . . . ?
C10 C11 C12 C13 171.9(9) . . . . ?
C11 C12 C13 C15 -60.3(14) . . . . ?
C11 C12 C13 C14 178.0(11) . . . . ?
C3B C2A C3A C2B 0(2) . . . . ?
C3B C2A C3A C3B -164(3) . . . 2 ?
C2A C3A C2B C3B 0(2) . . . . ?
C3B C3A C2B C3B 113(12) 2 . . . ?
C3A C2B C3B C2A 0(2) . . . . ?
C3A C2B C3B C3A 158(4) . . . 2_545 ?
C3A C2A C3B C2B 0(2) . . . . ?
C3A C2A C3B C3A -134(7) . . . 2_545 ?
 
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 H20 O4  0.849(15) 1.85(2) 2.690(9) 172(10) 2_545
O3 H21 O2  0.854(15) 1.79(3) 2.620(10) 165(9) 2
N1 H22 O2  0.849(13) 2.29(4) 3.112(13) 163(10) 2_655
 
_refine_diff_density_max    0.320
_refine_diff_density_min   -0.186
_refine_diff_density_rms    0.051

_shelxl_version_number 2013-4



#==END

 
data_kaw56
# 5-I
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C11 H11 N O6 S, C H2 Cl2'
_chemical_formula_sum
 'C12 H13 Cl2 N O6 S' 
_chemical_formula_weight          370.19

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'
 'Cl'  'Cl'   0.3639   0.7018
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.0738(1)
_cell_length_b                    8.1430(2)
_cell_length_c                    18.6485(4)
_cell_angle_alpha                 91.867(1)
_cell_angle_beta                  93.641(1)
_cell_angle_gamma                 97.715(2)
_cell_volume                      761.31(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     3256 
_cell_measurement_theta_min       4.757
_cell_measurement_theta_max       67.072
 
_exptl_crystal_description        'transparent plate' 
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.615          
_exptl_crystal_F_000              380
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.121
_exptl_crystal_size_mid           0.113
_exptl_crystal_size_min           0.012
_exptl_absorpt_coefficient_mu     5.394
_shelx_estimated_absorpt_T_min    0.561
_shelx_estimated_absorpt_T_max    0.938
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.561 
_exptl_absorpt_correction_T_max   0.938
_exptl_absorpt_process_details     
  'SADABS (Bruker, 2010)' 
 
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             13623
_diffrn_reflns_av_unetI/netI      0.0432
_diffrn_reflns_av_R_equivalents   0.0597
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.376
_diffrn_reflns_theta_max          67.922
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.965
_diffrn_measured_fraction_theta_full  0.968
_diffrn_reflns_Laue_measured_fraction_max    0.965
_diffrn_reflns_Laue_measured_fraction_full   0.968
_diffrn_reflns_point_group_measured_fraction_max   0.965
_diffrn_reflns_point_group_measured_fraction_full  0.968
_reflns_number_total              2669
_reflns_number_gt                 2051
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atom was located in a difference density map and
 refined using Ueq = 1.2 x Uiso and restrained with O/N-H bond distances
 of 0.85(2) angstroms. 
;
 
_computing_data_collection        'APEX2'
_computing_cell_refinement        'APEX2'
_computing_data_reduction         
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material   'XSEED (Barbour, 2001)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1211P)²+1.3386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2669
_refine_ls_number_parameters      208
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0804
_refine_ls_R_factor_gt            0.0619
_refine_ls_wR_factor_ref          0.1989
_refine_ls_wR_factor_gt           0.1825
_refine_ls_goodness_of_fit_ref    1.062
_refine_ls_restrained_S_all       1.062
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.6870(4) 1.0933(2) 0.42513(10) 0.0668(5) Uani 1 1 d . . . . .
Cl2 Cl 1.0021(3) 0.9901(2) 0.31041(9) 0.0562(5) Uani 1 1 d . . . . .
S1 S 0.5424(2) 0.55872(12) 0.23736(6) 0.0203(3) Uani 1 1 d . . . . .
O1 O -0.2050(6) -0.4084(4) 0.04856(17) 0.0238(7) Uani 1 1 d D . . . .
H1 H -0.276(10) -0.499(4) 0.032(3) 0.029 Uiso 1 1 d D U . . .
O2 O -0.5619(5) -0.3002(4) 0.00354(16) 0.0231(7) Uani 1 1 d . . . . .
O3 O 0.8102(6) 0.5426(4) 0.26216(18) 0.0272(7) Uani 1 1 d . . . . .
O4 O 0.4876(6) 0.6920(4) 0.19362(17) 0.0267(7) Uani 1 1 d . . . . .
O5 O 0.2499(8) 0.3703(5) 0.4738(2) 0.0418(9) Uani 1 1 d D . . . .
H4 H 0.163(11) 0.409(8) 0.507(3) 0.050 Uiso 1 1 d D U . . .
O6 O 0.0815(7) 0.5844(5) 0.42479(18) 0.0372(9) Uani 1 1 d . . . . .
N1 N 0.3787(7) 0.5771(5) 0.3092(2) 0.0243(8) Uani 1 1 d D . . . .
H7 H 0.226(6) 0.606(6) 0.302(3) 0.029 Uiso 1 1 d D U . . .
C1 C -0.3330(8) -0.2856(5) 0.0365(2) 0.0200(9) Uani 1 1 d . . . . .
C2 C -0.2086(8) -0.1192(5) 0.0620(2) 0.0203(9) Uani 1 1 d . . . . .
H2 H -0.2968 -0.0270 0.0499 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0227(8) -0.0915(5) 0.1014(2) 0.0202(9) Uani 1 1 d . . . . .
H3 H 0.1101 -0.1852 0.1114 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1541(8) 0.0695(5) 0.1306(2) 0.0196(9) Uani 1 1 d . . . . .
C5 C 0.0568(8) 0.2183(5) 0.1141(2) 0.0201(9) Uani 1 1 d . . . . .
H5 H -0.0946 0.2158 0.0812 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1776(8) 0.3675(5) 0.1448(2) 0.0203(9) Uani 1 1 d . . . . .
H6 H 0.1090 0.4673 0.1337 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4040(8) 0.3710(5) 0.1930(2) 0.0190(8) Uani 1 1 d . . . . .
C8 C 0.5064(8) 0.2256(5) 0.2082(2) 0.0217(9) Uani 1 1 d . . . . .
H8 H 0.6608 0.2285 0.2401 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3834(8) 0.0761(5) 0.1769(2) 0.0233(9) Uani 1 1 d . . . . .
H9 H 0.4556 -0.0231 0.1870 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2261(9) 0.4767(6) 0.4230(3) 0.0303(10) Uani 1 1 d . . . . .
C11 C 0.3902(10) 0.4477(6) 0.3612(3) 0.0308(10) Uani 1 1 d . . . . .
H11A H 0.5776 0.4462 0.3793 0.037 Uiso 1 1 calc R U . . .
H11B H 0.3236 0.3383 0.3374 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8397(17) 0.9320(9) 0.3884(4) 0.068(2) Uani 1 1 d . . . . .
H13B H 0.7030 0.8347 0.3763 0.081 Uiso 1 1 calc R U . . .
H13A H 0.9712 0.8989 0.4247 0.081 Uiso 1 1 calc R U . . .
 
 
_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
Cl1 C13 1.754(7) . ?
Cl2 C13 1.763(7) . ?
S1 O4 1.425(3) . ?
S1 O3 1.432(3) . ?
S1 N1 1.634(4) . ?
S1 C7 1.752(4) . ?
O1 C1 1.281(5) . ?
O1 H1 0.82(2) . ?
O2 C1 1.268(5) . ?
O5 C10 1.315(6) . ?
O5 H4 0.86(2) . ?
O6 C10 1.217(6) . ?
N1 C11 1.459(6) . ?
N1 H7 0.85(2) . ?
C1 C2 1.467(5) . ?
C2 C3 1.333(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.460(6) . ?
C3 H3 0.9500 . ?
C4 C9 1.398(6) . ?
C4 C5 1.405(6) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.494(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
 
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
O4 S1 O3 120.71(19) . . ?
O4 S1 N1 105.85(19) . . ?
O3 S1 N1 106.34(19) . . ?
O4 S1 C7 108.81(19) . . ?
O3 S1 C7 107.61(19) . . ?
N1 S1 C7 106.73(19) . . ?
C1 O1 H1 117(4) . . ?
C10 O5 H4 102(4) . . ?
C11 N1 S1 116.5(3) . . ?
C11 N1 H7 114(4) . . ?
S1 N1 H7 115(4) . . ?
O2 C1 O1 123.5(4) . . ?
O2 C1 C2 118.1(4) . . ?
O1 C1 C2 118.4(4) . . ?
C3 C2 C1 122.9(4) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 126.0(4) . . ?
C2 C3 H3 117.0 . . ?
C4 C3 H3 117.0 . . ?
C9 C4 C5 118.7(4) . . ?
C9 C4 C3 119.1(4) . . ?
C5 C4 C3 122.2(4) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 S1 120.3(3) . . ?
C6 C7 S1 119.4(3) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 120.7(4) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
O6 C10 O5 124.1(5) . . ?
O6 C10 C11 123.4(4) . . ?
O5 C10 C11 112.5(4) . . ?
N1 C11 C10 110.9(4) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
Cl1 C13 Cl2 112.1(4) . . ?
Cl1 C13 H13B 109.2 . . ?
Cl2 C13 H13B 109.2 . . ?
Cl1 C13 H13A 109.2 . . ?
Cl2 C13 H13A 109.2 . . ?
H13B C13 H13A 107.9 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O4 S1 N1 C11 176.5(3) . . . . ?
O3 S1 N1 C11 -54.0(4) . . . . ?
C7 S1 N1 C11 60.7(4) . . . . ?
O2 C1 C2 C3 175.3(4) . . . . ?
O1 C1 C2 C3 -4.8(6) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C9 173.7(4) . . . . ?
C2 C3 C4 C5 -5.9(7) . . . . ?
C9 C4 C5 C6 -2.5(6) . . . . ?
C3 C4 C5 C6 177.1(4) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C5 C6 C7 S1 -175.1(3) . . . . ?
O4 S1 C7 C8 155.6(3) . . . . ?
O3 S1 C7 C8 23.2(4) . . . . ?
N1 S1 C7 C8 -90.6(4) . . . . ?
O4 S1 C7 C6 -28.2(4) . . . . ?
O3 S1 C7 C6 -160.6(3) . . . . ?
N1 S1 C7 C6 85.6(4) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
S1 C7 C8 C9 175.1(3) . . . . ?
C7 C8 C9 C4 -0.8(7) . . . . ?
C5 C4 C9 C8 2.5(6) . . . . ?
C3 C4 C9 C8 -177.1(4) . . . . ?
S1 N1 C11 C10 -178.3(3) . . . . ?
O6 C10 C11 N1 7.2(7) . . . . ?
O5 C10 C11 N1 -174.7(4) . . . . ?
 
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 O2  0.82(2) 1.82(2) 2.631(4) 179(6) 2_445
O5 H4 O6  0.86(2) 1.84(3) 2.658(5) 159(6) 2_566
N1 H7 O3  0.85(2) 2.18(3) 2.935(5) 149(5) 1_455
 
_refine_diff_density_max    0.632
_refine_diff_density_min   -0.784
_refine_diff_density_rms    0.117

_shelxl_version_number 2013-4



#==END

 
data_kaw69
# rem 5-II squeezed data
 
# start Validation Reply Form
_vrf_PLAT420_kaw69
;
PROBLEM: D-H Without Acceptor      *O6     -  *H1     ...     Please Check 
RESPONSE: The acceptor group (most likely H2O) was ill-defined 
during the refinement process and removed via PLATON/SQUEEZE. 
;
# end Validation Reply Form


_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C11 H11 N O6 S' 
_chemical_formula_sum
 'C11 H11 N O6 S' 
_chemical_formula_weight          285.27

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    5.1963(1)
_cell_length_b                    29.5944(6)
_cell_length_c                    9.2515(2)
_cell_angle_alpha                 90
_cell_angle_beta                  99.075(1)
_cell_angle_gamma                 90
_cell_volume                      1404.90(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     8069
_cell_measurement_theta_min       2.987
_cell_measurement_theta_max       67.229
 
_exptl_crystal_description        'transparent needle' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.349          
_exptl_crystal_F_000              592
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.07
_exptl_absorpt_coefficient_mu     2.267
_shelx_estimated_absorpt_T_min    0.439
_shelx_estimated_absorpt_T_max    0.848 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.439
_exptl_absorpt_correction_T_max   0.484
_exptl_absorpt_process_details    
  'SADABS (Bruker, 2010)' 
 
_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  8.33
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  .  
_diffrn_standards_interval_time   .  
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             30432
_diffrn_reflns_av_unetI/netI      0.0217
_diffrn_reflns_av_R_equivalents   0.0506
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -35
_diffrn_reflns_limit_k_max        35
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.986
_diffrn_reflns_theta_max          68.239
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              2557
_reflns_number_gt                 2343
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1 -0.038  0.000  0.000       107        30 ' '
   2  0.001  0.500  0.500       107        30 ' '
_platon_squeeze_details
;
;

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

All non-hydrogen atoms were located in a single difference density map and 
 refined with anisotropic displacement parameters.  All CH hydrogen
 atoms were placed in calculated positions with Ueq = 1.2 x Uiso to
 the corresponding C atom (1.5 x Uiso for methyl H atoms).  Each OH
 and NH hydrogen atoms of the sulfonamidecinnamic acid molecule were
 located in a difference density map and refined using Ueq = 1.2 x Uiso
 and restrained with O/N-H bond distances of 0.85(2) angstroms.

The carboxylic acid group of the glycine fragment is disorded over
 two sites.  Because the refinement of the occupancy factors resulted
 in a nearly 1:1 ratio of components, the occupancy factor of
 each component was fixed at 50%. 


Significant attempts were made to locate additional solvent molecules
 hydrogen bonded to the carboxylic acid groups.  While several models
 were explored none were sufficient or chemically correct in explaining
 the nonbonded contacts.  Because the residual electron denisity peaks
 were located in isolated environments, it was determined that water
 was most likely the species present.  This waters are also likely  
 disordered over several sites.  For this reason, PLATON/SQUEEZE was
 utilized to exclude the solvent contributions to the diffraction pattern
 and help determine the number of waters in the void space.  From inspection
 of the SQUEEZE output, the void is described as having 30 electron counts 
 and a volume of 107 A3.  This is constent with three water molecules.
;
 
_computing_data_collection        'APEX2'
_computing_cell_refinement        'APEX2'
_computing_data_reduction         
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'XSEED (Barbour, 2001)'
_computing_publication_material   'XSEED (Barbour, 2001)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+2.3925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2557
_refine_ls_number_parameters      211
_refine_ls_number_restraints      10
_refine_ls_R_factor_all           0.0490
_refine_ls_R_factor_gt            0.0446
_refine_ls_wR_factor_ref          0.1123
_refine_ls_wR_factor_gt           0.1098
_refine_ls_goodness_of_fit_ref    1.073
_refine_ls_restrained_S_all       1.074
_refine_ls_shift/su_max           0.014
_refine_ls_shift/su_mean          0.002
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.41722(10) 0.23671(2) 0.44781(6) 0.01420(17) Uani 1 1 d . . . . .
O1 O -0.7721(4) 0.02496(6) 0.3932(2) 0.0288(4) Uani 1 1 d D . . . .
H10 H -0.900(5) 0.0078(10) 0.393(4) 0.035 Uiso 1 1 d D U . . .
O2 O -0.8311(4) 0.03232(6) 0.6255(2) 0.0313(5) Uani 1 1 d . . . . .
O3 O 0.5748(3) 0.22836(6) 0.33700(18) 0.0191(4) Uani 1 1 d . . . . .
O4 O 0.5389(3) 0.24430(6) 0.59651(17) 0.0190(4) Uani 1 1 d . . . . .
O5 O 0.134(3) 0.3726(4) 0.3727(15) 0.054(3) Uani 0.5 1 d . . P A 1
O6 O -0.118(4) 0.3705(8) 0.537(3) 0.036(3) Uani 0.5 1 d D . P A 1
H1 H -0.167(15) 0.3986(14) 0.503(9) 0.043 Uiso 0.5 1 d D U P B 1
N1 N 0.2507(4) 0.28193(7) 0.3968(2) 0.0165(4) Uani 1 1 d D . . . .
H4 H 0.187(5) 0.2804(9) 0.307(2) 0.020 Uiso 1 1 d D U . . .
C1 C -0.7156(5) 0.04265(8) 0.5236(3) 0.0249(6) Uani 1 1 d . . . . .
C2 C -0.5053(5) 0.07657(8) 0.5429(3) 0.0250(6) Uani 1 1 d . . . . .
H2 H -0.4599 0.0905 0.6359 0.030 Uiso 1 1 calc R U . . .
C3 C -0.3766(5) 0.08850(8) 0.4356(3) 0.0230(5) Uani 1 1 d . . . . .
H3 H -0.4202 0.0731 0.3450 0.028 Uiso 1 1 calc R U . . .
C4 C -0.1729(5) 0.12332(8) 0.4443(3) 0.0199(5) Uani 1 1 d . . . . .
C5 C -0.0595(5) 0.13244(8) 0.3210(3) 0.0210(5) Uani 1 1 d . . . . .
H5 H -0.1091 0.1151 0.2347 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1247(5) 0.16642(8) 0.3214(3) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.2001 0.1726 0.2364 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1965(4) 0.19123(8) 0.4487(3) 0.0157(5) Uani 1 1 d . . . . .
C8 C 0.0908(5) 0.18240(8) 0.5745(3) 0.0185(5) Uani 1 1 d . . . . .
H8 H 0.1436 0.1995 0.6609 0.022 Uiso 1 1 calc R U . . .
C9 C -0.0926(5) 0.14836(8) 0.5725(3) 0.0211(5) Uani 1 1 d . . . . .
H9 H -0.1646 0.1419 0.6585 0.025 Uiso 1 1 calc R U . . .
C10 C 0.037(4) 0.3513(6) 0.458(3) 0.017(3) Uani 0.5 1 d . U P A 1
C11 C 0.0832(5) 0.30107(8) 0.4938(3) 0.0199(5) Uani 1 1 d . U . . .
H11A H 0.1670 0.2976 0.5970 0.024 Uiso 1 1 calc R U . A 1
H11B H -0.0853 0.2848 0.4808 0.024 Uiso 1 1 calc R U . A 1
O5A O 0.045(2) 0.3630(4) 0.3347(13) 0.047(3) Uani 0.5 1 d . . P A 2
O6A O -0.183(4) 0.3627(7) 0.516(3) 0.038(4) Uani 0.5 1 d D . P A 2
H1A H -0.247(16) 0.3903(16) 0.488(9) 0.046 Uiso 0.5 1 d D U P C 2
C10A C -0.016(5) 0.3458(6) 0.438(3) 0.017(3) Uani 0.5 1 d . U P A 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O3 1.4307(17) . ?
S1 O4 1.4383(17) . ?
S1 N1 1.623(2) . ?
S1 C7 1.769(2) . ?
O1 C1 1.305(3) . ?
O1 H10 0.836(18) . ?
O2 C1 1.234(3) . ?
O5 C10 1.18(3) . ?
O6 C10 1.30(4) . ?
O6 H1 0.91(2) . ?
N1 C11 1.459(3) . ?
N1 H4 0.843(17) . ?
C1 C2 1.474(3) . ?
C2 C3 1.329(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.470(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 C9 1.405(4) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.535(19) . ?
C11 C10A 1.49(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O5A C10A 1.17(3) . ?
O6A C10A 1.32(4) . ?
O6A H1A 0.91(2) . ?
 
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
O3 S1 O4 119.83(10) . . ?
O3 S1 N1 105.84(10) . . ?
O4 S1 N1 106.44(10) . . ?
O3 S1 C7 108.46(10) . . ?
O4 S1 C7 107.59(10) . . ?
N1 S1 C7 108.20(10) . . ?
C1 O1 H10 108(2) . . ?
C10 O6 H1 112(6) . . ?
C11 N1 S1 118.92(16) . . ?
C11 N1 H4 117(2) . . ?
S1 N1 H4 110.4(19) . . ?
O2 C1 O1 122.8(2) . . ?
O2 C1 C2 121.1(2) . . ?
O1 C1 C2 116.1(2) . . ?
C3 C2 C1 122.8(3) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 126.1(2) . . ?
C2 C3 H3 117.0 . . ?
C4 C3 H3 117.0 . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 119.1(2) . . ?
C9 C4 C3 122.0(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 118.6(2) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 S1 119.10(18) . . ?
C8 C7 S1 119.32(18) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
O5 C10 O6 121(2) . . ?
O5 C10 C11 126(2) . . ?
O6 C10 C11 113(2) . . ?
N1 C11 C10A 109.8(13) . . ?
N1 C11 C10 109.4(12) . . ?
N1 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N1 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C10A O6A H1A 115(6) . . ?
O5A C10A O6A 125(2) . . ?
O5A C10A C11 123(2) . . ?
O6A C10A C11 111(2) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O3 S1 N1 C11 -175.68(17) . . . . ?
O4 S1 N1 C11 -47.2(2) . . . . ?
C7 S1 N1 C11 68.2(2) . . . . ?
O2 C1 C2 C3 179.9(3) . . . . ?
O1 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C4 C9 -0.2(4) . . . . ?
C9 C4 C5 C6 -1.8(4) . . . . ?
C3 C4 C5 C6 177.0(2) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 S1 -176.46(18) . . . . ?
O3 S1 C7 C6 -25.9(2) . . . . ?
O4 S1 C7 C6 -156.88(18) . . . . ?
N1 S1 C7 C6 88.5(2) . . . . ?
O3 S1 C7 C8 156.82(18) . . . . ?
O4 S1 C7 C8 25.8(2) . . . . ?
N1 S1 C7 C8 -88.8(2) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
S1 C7 C8 C9 176.54(18) . . . . ?
C7 C8 C9 C4 -0.7(4) . . . . ?
C5 C4 C9 C8 1.9(4) . . . . ?
C3 C4 C9 C8 -176.8(2) . . . . ?
S1 N1 C11 C10A 170.9(7) . . . . ?
S1 N1 C11 C10 157.0(7) . . . . ?
O5 C10 C11 N1 -5(2) . . . . ?
O6 C10 C11 N1 177.9(12) . . . . ?
O5 C10 C11 C10A -99(11) . . . . ?
O6 C10 C11 C10A 84(11) . . . . ?
N1 C11 C10A O5A -3.4(18) . . . . ?
C10 C11 C10A O5A 87(11) . . . . ?
N1 C11 C10A O6A 175.3(11) . . . . ?
C10 C11 C10A O6A -94(11) . . . . ?
 
_refine_diff_density_max    1.139
_refine_diff_density_min   -0.297
_refine_diff_density_rms    0.063

_shelxl_version_number 2013-4




