# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014


data_dead-iia

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N O6 S'
_chemical_formula_weight         423.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.1542(10)
_cell_length_b                   10.7836(15)
_cell_length_c                   13.6937(16)
_cell_angle_alpha                100.555(10)
_cell_angle_beta                 102.810(11)
_cell_angle_gamma                96.767(11)
_cell_volume                     998.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      0.937
_cell_measurement_theta_max      0.947

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7423
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         29.07
_reflns_number_total             5889
_reflns_number_gt                3645
_reflns_threshold_expression     >2sigma(I)

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

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1947P)²+2.7766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_number_reflns         5889
_refine_ls_number_parameters     541
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1788
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S -0.4352(4) -0.2796(2) -0.50621(19) 0.0334(6) Uani 1 1 d . . .
S1 S 0.0961(4) -0.1666(2) -0.47513(19) 0.0333(7) Uani 1 1 d . . .
O4 O 0.2086(17) -0.4491(10) -0.3456(8) 0.056(3) Uani 1 1 d . . .
O9 O -0.2593(17) -0.3210(9) -0.3241(7) 0.049(3) Uani 1 1 d . . .
O7 O 0.061(2) 0.0649(11) 0.0749(8) 0.078(4) Uani 1 1 d . . .
N2 N -0.3993(15) -0.0306(10) -0.4765(8) 0.035(2) Uani 1 1 d . . .
O12 O -0.7543(16) -0.4539(9) -0.8343(8) 0.055(3) Uani 1 1 d . . .
O11 O -0.5854(17) -0.4849(10) -0.6848(9) 0.058(3) Uani 1 1 d . . .
N1 N 0.0635(15) -0.4154(10) -0.5040(8) 0.030(2) Uani 1 1 d . . .
O6 O 0.4221(17) 0.0092(10) -0.1446(7) 0.055(3) Uani 1 1 d . . .
C35 C -0.6166(19) -0.2747(13) -0.7044(10) 0.038(3) Uani 1 1 d . . .
H35 H -0.6574 -0.2260 -0.7521 0.046 Uiso 1 1 calc R . .
O3 O -0.0780(16) -0.1239(10) -0.6573(8) 0.056(3) Uani 1 1 d . . .
O8 O 0.1982(18) -0.0966(13) 0.1380(8) 0.066(3) Uani 1 1 d . . .
O1 O -0.5364(19) -0.3492(11) -1.1159(8) 0.066(4) Uani 1 1 d . . .
O5 O 0.2518(16) 0.0358(10) -0.2976(8) 0.053(3) Uani 1 1 d . . .
O2 O -0.403(2) -0.5142(11) -1.0579(8) 0.077(4) Uani 1 1 d . . .
C28 C -0.087(2) -0.0633(13) -0.1036(8) 0.047(3) Uani 1 1 d . . .
H28 H -0.1430 0.0021 -0.1282 0.057 Uiso 1 1 calc R . .
C7 C -0.358(2) -0.4043(14) -0.9811(11) 0.047(3) Uani 1 1 d . . .
O10 O -0.5508(15) 0.0003(9) -0.6359(7) 0.049(3) Uani 1 1 d . . .
C17 C 0.0068(16) -0.5535(9) -0.5528(8) 0.030(2) Uani 1 1 d . . .
C43 C -0.097(2) 0.2828(14) -0.3538(12) 0.056(4) Uani 1 1 d . . .
H43 H 0.0336 0.3190 -0.3333 0.067 Uiso 1 1 calc R . .
C39 C -0.339(2) 0.1009(12) -0.4289(9) 0.041(3) Uani 1 1 d . . .
C24 C 0.098(2) -0.1373(13) 0.0347(9) 0.039(3) Uani 1 1 d . . .
C27 C -0.1098(19) -0.1805(14) -0.1664(10) 0.038(3) Uani 1 1 d . . .
C34 C -0.5309(16) -0.2153(10) -0.6114(10) 0.031(2) Uani 1 1 d . . .
C36 C -0.6524(15) -0.4107(12) -0.7383(10) 0.037(3) Uani 1 1 d . . .
C26 C -0.028(2) -0.2779(13) -0.1283(10) 0.042(3) Uani 1 1 d . . .
H26 H -0.0397 -0.3571 -0.1717 0.051 Uiso 1 1 calc R . .
C9 C -0.0738(17) -0.3395(11) -0.6575(9) 0.034(3) Uani 1 1 d . . .
H9 H -0.1065 -0.4231 -0.6956 0.041 Uiso 1 1 calc R . .
C33 C -0.5006(18) -0.0685(11) -0.5825(10) 0.038(3) Uani 1 1 d . . .
C11 C 0.1588(19) -0.3759(11) -0.4044(10) 0.033(3) Uani 1 1 d . . .
C25 C 0.072(2) -0.2585(14) -0.0268(11) 0.050(4) Uani 1 1 d . . .
H25 H 0.1204 -0.3250 -0.0003 0.060 Uiso 1 1 calc R . .
C10 C 0.0213(18) -0.3188(12) -0.5540(9) 0.031(3) Uani 1 1 d . . .
C5 C -0.233(2) -0.2683(11) -0.8176(9) 0.033(3) Uani 1 1 d . . .
C4 C -0.3120(19) -0.1687(12) -0.8575(10) 0.039(3) Uani 1 1 d . . .
H4 H -0.2892 -0.0877 -0.8151 0.046 Uiso 1 1 calc R . .
C30 C -0.2201(18) -0.2106(12) -0.2775(8) 0.036(3) Uani 1 1 d . . .
C32 C -0.3560(17) -0.1265(11) -0.4225(10) 0.030(3) Uani 1 1 d . . .
C31 C -0.2670(17) -0.1042(11) -0.3242(8) 0.032(3) Uani 1 1 d . . .
H31 H -0.2346 -0.0210 -0.2852 0.039 Uiso 1 1 calc R . .
C12 C 0.1913(18) -0.2372(13) -0.3736(8) 0.032(3) Uani 1 1 d . . .
C23 C 0.160(3) 0.0308(16) 0.1657(12) 0.078(6) Uani 1 1 d . . .
H23A H 0.0806 0.0349 0.2147 0.093 Uiso 1 1 calc R . .
H23B H 0.2813 0.0895 0.1968 0.093 Uiso 1 1 calc R . .
C3 C -0.423(2) -0.1872(14) -0.9581(10) 0.048(4) Uani 1 1 d . . .
H3 H -0.4818 -0.1227 -0.9826 0.058 Uiso 1 1 calc R . .
C22 C -0.190(2) -0.6041(13) -0.5845(10) 0.048(3) Uani 1 1 d . . .
H22 H -0.2806 -0.5507 -0.5762 0.058 Uiso 1 1 calc R . .
C44 C -0.1459(17) 0.1519(11) -0.3969(10) 0.040(3) Uani 1 1 d . . .
H44 H -0.0506 0.1015 -0.4035 0.047 Uiso 1 1 calc R . .
C8 C -0.1248(18) -0.2366(12) -0.7092(10) 0.035(3) Uani 1 1 d . . .
C6 C -0.259(2) -0.3918(11) -0.8826(10) 0.042(3) Uani 1 1 d . . .
H6 H -0.2115 -0.4600 -0.8585 0.050 Uiso 1 1 calc R . .
C40 C -0.486(2) 0.1752(11) -0.4195(11) 0.044(3) Uani 1 1 d . . .
H40 H -0.6171 0.1401 -0.4418 0.053 Uiso 1 1 calc R . .
C29 C 0.021(2) -0.0421(13) -0.0023(10) 0.040(3) Uani 1 1 d . . .
C21 C -0.252(3) -0.7329(14) -0.6282(12) 0.061(4) Uani 1 1 d . . .
H21 H -0.3834 -0.7676 -0.6516 0.073 Uiso 1 1 calc R . .
C41 C -0.421(3) 0.3065(16) -0.3737(13) 0.070(5) Uani 1 1 d . . .
H41 H -0.5131 0.3594 -0.3659 0.084 Uiso 1 1 calc R . .
C14 C 0.3091(19) -0.0312(13) -0.2434(9) 0.041(3) Uani 1 1 d . . .
C18 C 0.142(2) -0.6302(14) -0.5642(10) 0.051(4) Uani 1 1 d . . .
H18 H 0.2732 -0.5946 -0.5441 0.061 Uiso 1 1 calc R . .
C2 C -0.440(2) -0.3039(15) -1.0172(10) 0.043(3) Uani 1 1 d . . .
C15 C 0.450(3) 0.1438(15) -0.1045(15) 0.088(6) Uani 1 1 d . . .
H15A H 0.3254 0.1725 -0.1113 0.105 Uiso 1 1 calc R . .
H15B H 0.5240 0.1887 -0.1426 0.105 Uiso 1 1 calc R . .
C19 C 0.089(3) -0.7572(13) -0.6044(9) 0.055(5) Uani 1 1 d . . .
H19 H 0.1831 -0.8088 -0.6111 0.067 Uiso 1 1 calc R . .
C1 C -0.503(3) -0.4731(15) -1.1481(9) 0.061(4) Uani 1 1 d . . .
H1A H -0.4231 -0.4743 -1.1971 0.073 Uiso 1 1 calc R . .
H1B H -0.6247 -0.5301 -1.1809 0.073 Uiso 1 1 calc R . .
C37 C -0.804(3) -0.5956(15) -0.8712(13) 0.064(4) Uani 1 1 d . . .
H37A H -0.8941 -0.6313 -0.8364 0.076 Uiso 1 1 calc R . .
H37B H -0.6873 -0.6343 -0.8583 0.076 Uiso 1 1 calc R . .
C20 C -0.104(3) -0.8089(14) -0.6352(12) 0.068(5) Uani 1 1 d . . .
H20 H -0.1402 -0.8965 -0.6616 0.081 Uiso 1 1 calc R . .
C42 C -0.227(3) 0.3584(11) -0.3405(10) 0.065(5) Uani 1 1 d . . .
H42 H -0.1873 0.4446 -0.3094 0.078 Uiso 1 1 calc R . .
C38 C -0.895(3) -0.6202(17) -0.9861(16) 0.096(7) Uani 1 1 d . . .
H38A H -0.9227 -0.7106 -1.0143 0.144 Uiso 1 1 calc R . .
H38B H -0.8071 -0.5798 -1.0189 0.144 Uiso 1 1 calc R . .
H38C H -1.0140 -0.5856 -0.9976 0.144 Uiso 1 1 calc R . .
C13 C 0.287(2) -0.1743(12) -0.2743(9) 0.038(3) Uani 1 1 d . . .
H13 H 0.3377 -0.2206 -0.2266 0.045 Uiso 1 1 calc R . .
C16 C 0.555(3) 0.1716(15) 0.0038(13) 0.093(7) Uani 1 1 d . . .
H16A H 0.5797 0.2623 0.0304 0.140 Uiso 1 1 calc R . .
H16B H 0.6765 0.1401 0.0102 0.140 Uiso 1 1 calc R . .
H16C H 0.4784 0.1305 0.0417 0.140 Uiso 1 1 calc R . .


_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
S2 C34 1.751(12) . ?
S2 C32 1.777(12) . ?
S1 C12 1.751(11) . ?
S1 C10 1.741(13) . ?
O4 C11 1.253(14) . ?
O9 C30 1.211(15) . ?
O7 C29 1.368(17) . ?
O7 C23 1.421(17) . ?
N2 C33 1.430(16) . ?
N2 C32 1.402(14) . ?
N2 C39 1.420(16) . ?
O12 C36 1.322(15) . ?
O12 C37 1.491(17) . ?
O11 C36 1.247(15) . ?
N1 C11 1.346(17) . ?
N1 C10 1.374(15) . ?
N1 C17 1.484(14) . ?
O6 C14 1.375(15) . ?
O6 C15 1.427(16) . ?
C35 C34 1.292(17) . ?
C35 C36 1.429(17) . ?
O3 C8 1.256(16) . ?
O8 C24 1.400(15) . ?
O8 C23 1.432(19) . ?
O1 C1 1.395(18) . ?
O1 C2 1.343(17) . ?
O5 C14 1.171(14) . ?
O2 C7 1.386(17) . ?
O2 C1 1.455(16) . ?
C28 C27 1.362(19) . ?
C28 C29 1.393(16) . ?
C7 C6 1.351(17) . ?
C7 C2 1.406(19) . ?
O10 C33 1.165(15) . ?
C17 C18 1.361(18) . ?
C17 C22 1.386(19) . ?
C43 C42 1.33(2) . ?
C43 C44 1.396(18) . ?
C39 C44 1.365(19) . ?
C39 C40 1.410(18) . ?
C24 C29 1.346(18) . ?
C24 C25 1.39(2) . ?
C27 C26 1.390(19) . ?
C27 C30 1.507(16) . ?
C34 C33 1.536(15) . ?
C26 C25 1.379(19) . ?
C9 C10 1.394(16) . ?
C9 C8 1.461(16) . ?
C11 C12 1.453(17) . ?
C5 C4 1.412(16) . ?
C5 C6 1.426(17) . ?
C5 C8 1.470(17) . ?
C4 C3 1.395(16) . ?
C30 C31 1.450(15) . ?
C32 C31 1.319(15) . ?
C12 C13 1.385(16) . ?
C3 C2 1.34(2) . ?
C22 C21 1.385(19) . ?
C40 C41 1.42(2) . ?
C21 C20 1.42(2) . ?
C41 C42 1.38(2) . ?
C14 C13 1.503(17) . ?
C18 C19 1.353(19) . ?
C15 C16 1.46(2) . ?
C19 C20 1.37(2) . ?
C37 C38 1.53(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
C34 S2 C32 93.0(6) . . ?
C12 S1 C10 88.8(6) . . ?
C29 O7 C23 107.2(11) . . ?
C33 N2 C32 118.3(10) . . ?
C33 N2 C39 120.4(10) . . ?
C32 N2 C39 121.3(10) . . ?
C36 O12 C37 116.8(11) . . ?
C11 N1 C10 114.8(11) . . ?
C11 N1 C17 121.2(10) . . ?
C10 N1 C17 124.0(10) . . ?
C14 O6 C15 114.9(12) . . ?
C34 C35 C36 123.9(11) . . ?
C24 O8 C23 103.8(10) . . ?
C1 O1 C2 109.4(10) . . ?
C7 O2 C1 103.8(11) . . ?
C27 C28 C29 119.5(12) . . ?
C6 C7 O2 126.7(13) . . ?
C6 C7 C2 122.5(13) . . ?
O2 C7 C2 110.7(13) . . ?
C18 C17 C22 120.3(11) . . ?
C18 C17 N1 121.6(11) . . ?
C22 C17 N1 118.0(11) . . ?
C42 C43 C44 123.8(15) . . ?
C44 C39 C40 122.4(13) . . ?
C44 C39 N2 120.5(11) . . ?
C40 C39 N2 117.0(13) . . ?
C29 C24 O8 111.6(12) . . ?
C29 C24 C25 121.0(12) . . ?
O8 C24 C25 127.4(12) . . ?
C28 C27 C26 119.7(13) . . ?
C28 C27 C30 122.9(11) . . ?
C26 C27 C30 117.4(13) . . ?
C35 C34 C33 119.9(11) . . ?
C35 C34 S2 128.6(10) . . ?
C33 C34 S2 111.5(8) . . ?
O11 C36 O12 121.2(12) . . ?
O11 C36 C35 123.7(12) . . ?
O12 C36 C35 115.0(11) . . ?
C25 C26 C27 120.8(14) . . ?
C10 C9 C8 123.4(11) . . ?
O10 C33 N2 125.7(11) . . ?
O10 C33 C34 127.1(12) . . ?
N2 C33 C34 107.2(10) . . ?
O4 C11 N1 124.5(12) . . ?
O4 C11 C12 124.5(12) . . ?
N1 C11 C12 110.9(9) . . ?
C26 C25 C24 118.3(12) . . ?
C9 C10 N1 123.7(12) . . ?
C9 C10 S1 122.8(10) . . ?
N1 C10 S1 113.5(9) . . ?
C4 C5 C6 119.6(12) . . ?
C4 C5 C8 116.8(11) . . ?
C6 C5 C8 123.6(10) . . ?
C5 C4 C3 122.5(13) . . ?
O9 C30 C31 123.4(10) . . ?
O9 C30 C27 118.9(11) . . ?
C31 C30 C27 117.7(11) . . ?
C31 C32 N2 124.2(11) . . ?
C31 C32 S2 125.8(9) . . ?
N2 C32 S2 110.0(9) . . ?
C32 C31 C30 119.4(11) . . ?
C13 C12 C11 121.4(11) . . ?
C13 C12 S1 126.7(11) . . ?
C11 C12 S1 111.9(8) . . ?
O7 C23 O8 107.9(12) . . ?
C2 C3 C4 115.9(11) . . ?
C21 C22 C17 121.0(14) . . ?
C39 C44 C43 117.4(13) . . ?
O3 C8 C9 117.8(12) . . ?
O3 C8 C5 122.7(11) . . ?
C9 C8 C5 119.5(11) . . ?
C7 C6 C5 116.2(11) . . ?
C41 C40 C39 115.8(14) . . ?
C24 C29 O7 109.0(12) . . ?
C24 C29 C28 120.7(13) . . ?
O7 C29 C28 130.3(12) . . ?
C22 C21 C20 116.2(15) . . ?
C40 C41 C42 122.0(13) . . ?
O5 C14 O6 125.4(13) . . ?
O5 C14 C13 125.2(12) . . ?
O6 C14 C13 109.1(10) . . ?
C17 C18 C19 121.2(15) . . ?
C3 C2 O1 129.3(12) . . ?
C3 C2 C7 123.1(12) . . ?
O1 C2 C7 107.6(13) . . ?
O6 C15 C16 109.1(14) . . ?
C20 C19 C18 119.2(14) . . ?
O1 C1 O2 107.7(11) . . ?
O12 C37 C38 106.4(12) . . ?
C19 C20 C21 122.1(13) . . ?
C43 C42 C41 118.6(12) . . ?
C12 C13 C14 120.1(11) . . ?

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 972111'

data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O4 S2'
_chemical_formula_sum            'C16 H17 N O4 S2'
_chemical_formula_weight         351.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   5.2501(3)
_cell_length_b                   12.3403(6)
_cell_length_c                   25.2776(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.844(6)
_cell_angle_gamma                90.00
_cell_volume                     1636.83(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2037
_cell_measurement_theta_min      3.2188
_cell_measurement_theta_max      29.0524

_exptl_crystal_description       Solid
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7196
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         29.12
_reflns_number_total             4404
_reflns_number_gt                2699
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.2703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4404
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2AA S 0.14927(11) 0.10473(5) 0.14587(2) 0.04282(18) Uani 1 1 d . . .
S0AA S 0.89618(12) 0.17349(5) 0.30403(3) 0.0526(2) Uani 1 1 d . . .
O O -0.2674(3) -0.10445(13) 0.02708(7) 0.0536(5) Uani 1 1 d . . .
N1 N -0.0413(3) 0.30012(14) 0.14386(7) 0.0370(4) Uani 1 1 d . . .
O2AA O 0.5113(3) 0.10961(13) 0.22393(8) 0.0650(6) Uani 1 1 d . . .
O0AA O -0.3586(3) 0.28918(14) 0.07982(7) 0.0564(5) Uani 1 1 d . . .
O1AA O 0.0595(3) -0.08522(14) 0.08579(7) 0.0571(5) Uani 1 1 d . . .
C1AA C 0.6714(4) 0.25537(18) 0.27372(9) 0.0383(5) Uani 1 1 d . . .
C2AA C -0.1877(4) 0.24736(18) 0.10580(9) 0.0399(5) Uani 1 1 d . . .
C3AA C 0.1455(4) 0.23862(17) 0.16980(9) 0.0363(5) Uani 1 1 d . . .
C4AA C 0.4944(4) 0.20667(19) 0.23435(9) 0.0425(5) Uani 1 1 d . . .
C5AA C -0.1219(4) -0.04793(19) 0.06168(9) 0.0429(5) Uani 1 1 d . . .
C6AA C -0.1013(4) 0.13285(18) 0.10113(9) 0.0384(5) Uani 1 1 d . . .
C7AA C 0.3046(4) 0.2757(2) 0.20847(9) 0.0414(5) Uani 1 1 d . . .
C8AA C -0.2105(4) 0.0640(2) 0.06670(10) 0.0431(6) Uani 1 1 d . . .
C9AA C -0.0826(4) 0.41530(18) 0.15580(9) 0.0402(5) Uani 1 1 d . . .
H9A1 H -0.0815 0.4246 0.1939 0.048 Uiso 1 1 calc R . .
H9A2 H -0.2499 0.4363 0.1420 0.048 Uiso 1 1 calc R . .
C0BA C 0.1147(4) 0.49040(18) 0.13304(9) 0.0429(6) Uani 1 1 d . . .
H0B1 H 0.0826 0.5634 0.1454 0.052 Uiso 1 1 calc R . .
H0B2 H 0.2817 0.4690 0.1469 0.052 Uiso 1 1 calc R . .
C1BA C 0.6993(4) 0.36168(19) 0.28956(9) 0.0425(5) Uani 1 1 d . . .
H1BA H 0.5942 0.4180 0.2778 0.051 Uiso 1 1 calc R . .
C2BA C 1.0271(5) 0.2810(2) 0.33734(10) 0.0552(7) Uani 1 1 d . . .
H2BA H 1.1662 0.2754 0.3609 0.066 Uiso 1 1 calc R . .
C3BA C 0.9070(5) 0.3747(2) 0.32581(10) 0.0525(7) Uani 1 1 d . . .
H3BA H 0.9558 0.4411 0.3402 0.063 Uiso 1 1 calc R . .
C4BA C -0.2018(5) -0.2174(2) 0.02159(12) 0.0640(8) Uani 1 1 d . . .
H4B1 H -0.3158 -0.2508 -0.0040 0.096 Uiso 1 1 calc R . .
H4B2 H -0.2159 -0.2531 0.0551 0.096 Uiso 1 1 calc R . .
H4B3 H -0.0300 -0.2234 0.0100 0.096 Uiso 1 1 calc R . .
C5BA C 0.3154(5) 0.5717(2) 0.05342(10) 0.0588(7) Uani 1 1 d . . .
H5B1 H 0.3119 0.5701 0.0154 0.088 Uiso 1 1 calc R . .
H5B2 H 0.4822 0.5518 0.0667 0.088 Uiso 1 1 calc R . .
H5B3 H 0.2752 0.6434 0.0653 0.088 Uiso 1 1 calc R . .
C6BA C 0.1210(5) 0.4924(2) 0.07365(10) 0.0542(7) Uani 1 1 d . . .
H6B1 H -0.0465 0.5118 0.0594 0.065 Uiso 1 1 calc R . .
H6B2 H 0.1607 0.4203 0.0610 0.065 Uiso 1 1 calc R . .
H2 H 0.283(4) 0.341(2) 0.2185(10) 0.049(7) Uiso 1 1 d . . .
H1 H -0.334(4) 0.087(2) 0.0441(10) 0.054(7) Uiso 1 1 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
S2AA C6AA 1.742(2) . ?
S2AA C3AA 1.760(2) . ?
S0AA C2BA 1.704(3) . ?
S0AA C1AA 1.716(2) . ?
O C5AA 1.339(3) . ?
O C4BA 1.444(3) . ?
N1 C2AA 1.376(3) . ?
N1 C3AA 1.388(2) . ?
N1 C9AA 1.471(3) . ?
O2AA C4AA 1.230(3) . ?
O0AA C2AA 1.210(2) . ?
O1AA C5AA 1.206(3) . ?
C1AA C1BA 1.378(3) . ?
C1AA C4AA 1.468(3) . ?
C2AA C6AA 1.490(3) . ?
C3AA C7AA 1.345(3) . ?
C4AA C7AA 1.451(3) . ?
C5AA C8AA 1.465(3) . ?
C6AA C8AA 1.332(3) . ?
C7AA H2 0.85(3) . ?
C8AA H1 0.90(2) . ?
C9AA C0BA 1.517(3) . ?
C9AA H9A1 0.9700 . ?
C9AA H9A2 0.9700 . ?
C0BA C6BA 1.503(3) . ?
C0BA H0B1 0.9700 . ?
C0BA H0B2 0.9700 . ?
C1BA C3BA 1.411(3) . ?
C1BA H1BA 0.9300 . ?
C2BA C3BA 1.344(4) . ?
C2BA H2BA 0.9300 . ?
C3BA H3BA 0.9300 . ?
C4BA H4B1 0.9600 . ?
C4BA H4B2 0.9600 . ?
C4BA H4B3 0.9600 . ?
C5BA C6BA 1.515(3) . ?
C5BA H5B1 0.9600 . ?
C5BA H5B2 0.9600 . ?
C5BA H5B3 0.9600 . ?
C6BA H6B1 0.9700 . ?
C6BA H6B2 0.9700 . ?

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
C6AA S2AA C3AA 91.12(10) . . ?
C2BA S0AA C1AA 91.32(12) . . ?
C5AA O C4BA 115.66(18) . . ?
C2AA N1 C3AA 116.23(18) . . ?
C2AA N1 C9AA 121.19(17) . . ?
C3AA N1 C9AA 122.57(17) . . ?
C1BA C1AA C4AA 130.2(2) . . ?
C1BA C1AA S0AA 111.45(16) . . ?
C4AA C1AA S0AA 118.22(17) . . ?
O0AA C2AA N1 124.4(2) . . ?
O0AA C2AA C6AA 125.7(2) . . ?
N1 C2AA C6AA 109.85(17) . . ?
C7AA C3AA N1 124.8(2) . . ?
C7AA C3AA S2AA 123.74(17) . . ?
N1 C3AA S2AA 111.50(15) . . ?
O2AA C4AA C7AA 121.9(2) . . ?
O2AA C4AA C1AA 119.7(2) . . ?
C7AA C4AA C1AA 118.4(2) . . ?
O1AA C5AA O 123.8(2) . . ?
O1AA C5AA C8AA 124.4(2) . . ?
O C5AA C8AA 111.84(18) . . ?
C8AA C6AA C2AA 122.04(19) . . ?
C8AA C6AA S2AA 126.68(18) . . ?
C2AA C6AA S2AA 111.28(16) . . ?
C3AA C7AA C4AA 122.0(2) . . ?
C3AA C7AA H2 116.9(16) . . ?
C4AA C7AA H2 121.0(16) . . ?
C6AA C8AA C5AA 121.8(2) . . ?
C6AA C8AA H1 119.9(16) . . ?
C5AA C8AA H1 118.2(16) . . ?
N1 C9AA C0BA 113.90(18) . . ?
N1 C9AA H9A1 108.8 . . ?
C0BA C9AA H9A1 108.8 . . ?
N1 C9AA H9A2 108.8 . . ?
C0BA C9AA H9A2 108.8 . . ?
H9A1 C9AA H9A2 107.7 . . ?
C6BA C0BA C9AA 115.20(19) . . ?
C6BA C0BA H0B1 108.5 . . ?
C9AA C0BA H0B1 108.5 . . ?
C6BA C0BA H0B2 108.5 . . ?
C9AA C0BA H0B2 108.5 . . ?
H0B1 C0BA H0B2 107.5 . . ?
C1AA C1BA C3BA 111.7(2) . . ?
C1AA C1BA H1BA 124.1 . . ?
C3BA C1BA H1BA 124.1 . . ?
C3BA C2BA S0AA 112.55(17) . . ?
C3BA C2BA H2BA 123.7 . . ?
S0AA C2BA H2BA 123.7 . . ?
C2BA C3BA C1BA 113.0(2) . . ?
C2BA C3BA H3BA 123.5 . . ?
C1BA C3BA H3BA 123.5 . . ?
O C4BA H4B1 109.5 . . ?
O C4BA H4B2 109.5 . . ?
H4B1 C4BA H4B2 109.5 . . ?
O C4BA H4B3 109.5 . . ?
H4B1 C4BA H4B3 109.5 . . ?
H4B2 C4BA H4B3 109.5 . . ?
C6BA C5BA H5B1 109.5 . . ?
C6BA C5BA H5B2 109.5 . . ?
H5B1 C5BA H5B2 109.5 . . ?
C6BA C5BA H5B3 109.5 . . ?
H5B1 C5BA H5B3 109.5 . . ?
H5B2 C5BA H5B3 109.5 . . ?
C0BA C6BA C5BA 112.6(2) . . ?
C0BA C6BA H6B1 109.1 . . ?
C5BA C6BA H6B1 109.1 . . ?
C0BA C6BA H6B2 109.1 . . ?
C5BA C6BA H6B2 109.1 . . ?
H6B1 C6BA H6B2 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.850
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 961594'
