# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pd_jp79_0m
_database_code_depnum_ccdc_archive 'CCDC 1038268'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-benzoylthiazolidin-2-one
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O4 S2'
_chemical_formula_weight         414.48

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   11.222(2)
_cell_length_b                   12.458(3)
_cell_length_c                   13.769(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.055(11)
_cell_angle_gamma                90.00
_cell_volume                     1924.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8834
_exptl_absorpt_correction_T_max  0.9324
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(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_reflns_number            12019
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.45
_reflns_number_total             3538
_reflns_number_gt                2608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0630P)²+0.1961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3538
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33444(8) 0.35237(5) 0.51579(5) 0.0492(3) Uani 1 1 d . . .
S2 S 0.76593(8) 0.82997(6) -0.00512(5) 0.0529(3) Uani 1 1 d . . .
O1 O 0.30972(17) 0.25824(14) 0.34510(13) 0.0433(5) Uani 1 1 d . . .
O2 O 0.34872(18) -0.02851(14) 0.47271(14) 0.0501(5) Uani 1 1 d . . .
O3 O 0.69247(18) 0.75268(15) 0.16049(13) 0.0514(5) Uani 1 1 d . . .
N1 N 0.36691(18) 0.15194(15) 0.47580(14) 0.0314(5) Uani 1 1 d . . .
N2 N 0.59812(18) 0.69083(16) 0.02050(14) 0.0324(5) Uani 1 1 d . . .
O4 O 0.40825(19) 0.63294(19) 0.01627(15) 0.0631(6) Uani 1 1 d . . .
C1 C 0.3964(3) 0.2675(2) 0.60979(18) 0.0442(7) Uani 1 1 d . . .
H1A H 0.4836 0.2724 0.6119 0.053 Uiso 1 1 calc R . .
H1B H 0.3657 0.2874 0.6735 0.053 Uiso 1 1 calc R . .
C2 C 0.3565(3) 0.1563(2) 0.58155(17) 0.0372(6) Uani 1 1 d . . .
H2A H 0.4075 0.1020 0.6127 0.045 Uiso 1 1 calc R . .
H2B H 0.2739 0.1440 0.6006 0.045 Uiso 1 1 calc R . .
C3 C 0.3745(2) 0.0527(2) 0.42949(18) 0.0348(6) Uani 1 1 d . . .
C4 C 0.4259(2) 0.0490(2) 0.33070(18) 0.0335(6) Uani 1 1 d . . .
C5 C 0.5245(2) 0.1107(2) 0.3079(2) 0.0403(7) Uani 1 1 d . . .
H5 H 0.5519 0.1640 0.3512 0.048 Uiso 1 1 calc R . .
C6 C 0.5819(3) 0.0938(3) 0.2220(2) 0.0494(8) Uani 1 1 d . . .
H6 H 0.6497 0.1346 0.2073 0.059 Uiso 1 1 calc R . .
C7 C 0.5410(3) 0.0181(3) 0.1578(2) 0.0574(9) Uani 1 1 d . . .
H7 H 0.5809 0.0073 0.0992 0.069 Uiso 1 1 calc R . .
C8 C 0.3348(2) 0.24740(19) 0.42966(18) 0.0326(6) Uani 1 1 d . . .
C9 C 0.3855(3) -0.0281(2) 0.2653(2) 0.0429(7) Uani 1 1 d . . .
H9 H 0.3194 -0.0708 0.2804 0.052 Uiso 1 1 calc R . .
C10 C 0.4423(3) -0.0423(3) 0.1778(2) 0.0551(8) Uani 1 1 d . . .
H10 H 0.4135 -0.0930 0.1326 0.066 Uiso 1 1 calc R . .
C11 C 0.5333(3) 0.4557(2) 0.3201(2) 0.0440(7) Uani 1 1 d . . .
H11 H 0.5384 0.4132 0.3764 0.053 Uiso 1 1 calc R . .
C12 C 0.6301(2) 0.4626(2) 0.25964(19) 0.0405(7) Uani 1 1 d . . .
H12 H 0.7005 0.4246 0.2745 0.049 Uiso 1 1 calc R . .
C13 C 0.6227(2) 0.52562(19) 0.17745(18) 0.0339(6) Uani 1 1 d . . .
H13 H 0.6886 0.5318 0.1367 0.041 Uiso 1 1 calc R . .
C14 C 0.5183(2) 0.57976(19) 0.15495(17) 0.0295(6) Uani 1 1 d . . .
C15 C 0.5013(2) 0.6368(2) 0.06163(18) 0.0354(6) Uani 1 1 d . . .
C16 C 0.5869(3) 0.7198(3) -0.08188(19) 0.0549(8) Uani 1 1 d . . .
H16A H 0.5238 0.7734 -0.0914 0.066 Uiso 1 1 calc R . .
H16B H 0.5670 0.6564 -0.1211 0.066 Uiso 1 1 calc R . .
C17 C 0.7048(3) 0.7649(2) -0.1110(2) 0.0551(9) Uani 1 1 d . . .
H17A H 0.6943 0.8165 -0.1642 0.066 Uiso 1 1 calc R . .
H17B H 0.7578 0.7074 -0.1325 0.066 Uiso 1 1 calc R . .
C18 C 0.6806(2) 0.75052(19) 0.07367(18) 0.0345(6) Uani 1 1 d . . .
C19 C 0.4297(2) 0.5104(2) 0.2984(2) 0.0426(7) Uani 1 1 d . . .
H19 H 0.3647 0.5060 0.3404 0.051 Uiso 1 1 calc R . .
C20 C 0.4212(2) 0.5716(2) 0.21550(19) 0.0372(6) Uani 1 1 d . . .
H20 H 0.3499 0.6078 0.1998 0.045 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
S1 C8 1.765(3) . ?
S1 C1 1.801(3) . ?
S2 C18 1.764(2) . ?
S2 C17 1.794(3) . ?
O1 C8 1.200(3) . ?
O2 C3 1.211(3) . ?
O3 C18 1.201(3) . ?
N1 C8 1.393(3) . ?
N1 C3 1.395(3) . ?
N1 C2 1.464(3) . ?
N2 C18 1.386(3) . ?
N2 C15 1.407(3) . ?
N2 C16 1.458(3) . ?
O4 C15 1.207(3) . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.488(3) . ?
C4 C9 1.387(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.367(4) . ?
C6 H6 0.9400 . ?
C7 C10 1.371(4) . ?
C7 H7 0.9400 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C19 1.376(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9400 . ?
C14 C20 1.388(3) . ?
C14 C15 1.477(3) . ?
C16 C17 1.499(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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
C8 S1 C1 92.41(12) . . ?
C18 S2 C17 92.44(13) . . ?
C8 N1 C3 124.5(2) . . ?
C8 N1 C2 113.41(19) . . ?
C3 N1 C2 119.63(19) . . ?
C18 N2 C15 123.9(2) . . ?
C18 N2 C16 115.0(2) . . ?
C15 N2 C16 117.0(2) . . ?
C2 C1 S1 104.22(19) . . ?
C2 C1 H1A 110.9 . . ?
S1 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
S1 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
N1 C2 C1 105.21(19) . . ?
N1 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
N1 C2 H2B 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O2 C3 N1 119.9(2) . . ?
O2 C3 C4 121.6(2) . . ?
N1 C3 C4 118.2(2) . . ?
C9 C4 C5 119.3(2) . . ?
C9 C4 C3 119.2(2) . . ?
C5 C4 C3 120.9(2) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C10 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C10 C7 H7 119.6 . . ?
O1 C8 N1 126.3(2) . . ?
O1 C8 S1 124.4(2) . . ?
N1 C8 S1 109.27(18) . . ?
C10 C9 C4 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C7 C10 C9 119.4(3) . . ?
C7 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C19 C11 C12 120.6(2) . . ?
C19 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C20 120.1(2) . . ?
C13 C14 C15 121.7(2) . . ?
C20 C14 C15 117.8(2) . . ?
O4 C15 N2 118.5(2) . . ?
O4 C15 C14 121.9(2) . . ?
N2 C15 C14 119.4(2) . . ?
N2 C16 C17 106.9(2) . . ?
N2 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
N2 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 S2 106.12(18) . . ?
C16 C17 H17A 110.5 . . ?
S2 C17 H17A 110.5 . . ?
C16 C17 H17B 110.5 . . ?
S2 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
O3 C18 N2 126.8(2) . . ?
O3 C18 S2 123.2(2) . . ?
N2 C18 S2 109.94(17) . . ?
C20 C19 C11 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C11 C19 H19 120.0 . . ?
C19 C20 C14 119.7(2) . . ?
C19 C20 H20 120.1 . . ?
C14 C20 H20 120.1 . . ?

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
C8 S1 C1 C2 -27.20(19) . . . . ?
C8 N1 C2 C1 -37.8(3) . . . . ?
C3 N1 C2 C1 159.3(2) . . . . ?
S1 C1 C2 N1 39.6(2) . . . . ?
C8 N1 C3 O2 -146.1(2) . . . . ?
C2 N1 C3 O2 14.8(4) . . . . ?
C8 N1 C3 C4 39.9(4) . . . . ?
C2 N1 C3 C4 -159.2(2) . . . . ?
O2 C3 C4 C9 37.3(4) . . . . ?
N1 C3 C4 C9 -148.9(2) . . . . ?
O2 C3 C4 C5 -133.5(3) . . . . ?
N1 C3 C4 C5 40.4(3) . . . . ?
C9 C4 C5 C6 -1.0(4) . . . . ?
C3 C4 C5 C6 169.7(2) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C10 -0.1(5) . . . . ?
C3 N1 C8 O1 -0.2(4) . . . . ?
C2 N1 C8 O1 -162.1(2) . . . . ?
C3 N1 C8 S1 179.04(19) . . . . ?
C2 N1 C8 S1 17.1(3) . . . . ?
C1 S1 C8 O1 -173.9(2) . . . . ?
C1 S1 C8 N1 6.90(18) . . . . ?
C5 C4 C9 C10 -0.7(4) . . . . ?
C3 C4 C9 C10 -171.6(2) . . . . ?
C6 C7 C10 C9 -1.6(5) . . . . ?
C4 C9 C10 C7 2.0(4) . . . . ?
C19 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C20 0.6(4) . . . . ?
C12 C13 C14 C15 -172.1(2) . . . . ?
C18 N2 C15 O4 144.1(3) . . . . ?
C16 N2 C15 O4 -12.0(4) . . . . ?
C18 N2 C15 C14 -40.4(3) . . . . ?
C16 N2 C15 C14 163.5(2) . . . . ?
C13 C14 C15 O4 138.4(3) . . . . ?
C20 C14 C15 O4 -34.4(4) . . . . ?
C13 C14 C15 N2 -36.9(3) . . . . ?
C20 C14 C15 N2 150.2(2) . . . . ?
C18 N2 C16 C17 27.9(3) . . . . ?
C15 N2 C16 C17 -173.9(2) . . . . ?
N2 C16 C17 S2 -32.0(3) . . . . ?
C18 S2 C17 C16 23.7(2) . . . . ?
C15 N2 C18 O3 11.4(4) . . . . ?
C16 N2 C18 O3 167.9(3) . . . . ?
C15 N2 C18 S2 -166.39(19) . . . . ?
C16 N2 C18 S2 -9.9(3) . . . . ?
C17 S2 C18 O3 173.3(3) . . . . ?
C17 S2 C18 N2 -8.8(2) . . . . ?
C12 C11 C19 C20 0.8(4) . . . . ?
C11 C19 C20 C14 -1.4(4) . . . . ?
C13 C14 C20 C19 0.7(4) . . . . ?
C15 C14 C20 C19 173.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.45
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.075
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JP_73
_database_code_depnum_ccdc_archive 'CCDC 1038269'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            phenyl(2-thioxooxazolidin-3-yl)methanone
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N O2 S'
_chemical_formula_weight         207.24

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           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 2 (1)'

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

_cell_length_a                   13.7485(7)
_cell_length_b                   5.4360(3)
_cell_length_c                   25.0630(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1873.13(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7464
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8713
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11582
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.30
_reflns_number_total             3362
_reflns_number_gt                3149
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0727P)²+0.7451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       'not measured'
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(8)
_refine_ls_number_reflns         3362
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78891(5) 0.31516(15) 0.59618(3) 0.0185(2) Uani 1 1 d . . .
S2 S 0.45628(5) -0.14643(15) 0.49297(3) 0.0175(2) Uani 1 1 d . . .
O1 O 0.60514(15) 0.2633(4) 0.57596(8) 0.0167(5) Uani 1 1 d . . .
O2 O 0.63181(17) 0.9094(5) 0.68101(9) 0.0217(5) Uani 1 1 d . . .
O3 O 0.63862(15) -0.2351(4) 0.51046(9) 0.0174(5) Uani 1 1 d . . .
O4 O 0.62444(16) 0.4283(4) 0.41049(10) 0.0209(5) Uani 1 1 d . . .
C2 C 0.5084(2) 0.3481(6) 0.59160(15) 0.0194(7) Uani 1 1 d . . .
H2A H 0.4756 0.2249 0.6145 0.023 Uiso 1 1 calc R . .
H2B H 0.4675 0.3798 0.5598 0.023 Uiso 1 1 calc R . .
C4 C 0.5270(2) 0.5825(6) 0.62202(14) 0.0185(7) Uani 1 1 d . . .
H4A H 0.5198 0.7293 0.5990 0.022 Uiso 1 1 calc R . .
H4B H 0.4835 0.5979 0.6533 0.022 Uiso 1 1 calc R . .
N5 N 0.62937(18) 0.5436(5) 0.63819(11) 0.0140(6) Uani 1 1 d . . .
N6 N 0.62058(18) 0.0534(5) 0.44936(11) 0.0156(6) Uani 1 1 d . . .
C7 C 0.6728(2) 0.7160(6) 0.67224(12) 0.0150(7) Uani 1 1 d . . .
C8 C 0.7652(2) 0.6466(6) 0.70000(13) 0.0151(7) Uani 1 1 d . . .
C9 C 0.7700(2) 0.4281(6) 0.72852(15) 0.0202(7) Uani 1 1 d . . .
H9 H 0.7185 0.3120 0.7265 0.024 Uiso 1 1 calc R . .
C10 C 0.8508(3) 0.3812(6) 0.75998(14) 0.0197(7) Uani 1 1 d . . .
H10 H 0.8536 0.2355 0.7809 0.024 Uiso 1 1 calc R . .
C11 C 0.9275(2) 0.5463(6) 0.76104(14) 0.0209(7) Uani 1 1 d . . .
H11 H 0.9833 0.5114 0.7821 0.025 Uiso 1 1 calc R . .
C12 C 0.6733(2) 0.3772(5) 0.60508(13) 0.0156(7) Uani 1 1 d . . .
C13 C 0.8413(2) 0.8134(6) 0.70138(13) 0.0166(7) Uani 1 1 d . . .
H13 H 0.8372 0.9625 0.6817 0.020 Uiso 1 1 calc R . .
C14 C 0.9236(2) 0.7627(6) 0.73152(14) 0.0202(7) Uani 1 1 d . . .
H14 H 0.9767 0.8745 0.7320 0.024 Uiso 1 1 calc R . .
C15 C 0.7371(2) -0.1706(6) 0.49311(15) 0.0179(7) Uani 1 1 d . . .
H15A H 0.7642 -0.2989 0.4693 0.022 Uiso 1 1 calc R . .
H15B H 0.7810 -0.1495 0.5241 0.022 Uiso 1 1 calc R . .
C16 C 0.7239(2) 0.0700(6) 0.46344(13) 0.0172(7) Uani 1 1 d . . .
H16A H 0.7373 0.2135 0.4866 0.021 Uiso 1 1 calc R . .
H16B H 0.7657 0.0785 0.4313 0.021 Uiso 1 1 calc R . .
C17 C 0.5793(2) 0.2401(6) 0.41768(12) 0.0159(7) Uani 1 1 d . . .
C18 C 0.4859(2) 0.1900(6) 0.38942(13) 0.0153(7) Uani 1 1 d . . .
C19 C 0.4143(2) 0.3696(6) 0.38896(13) 0.0176(7) Uani 1 1 d . . .
H19 H 0.4223 0.5152 0.4095 0.021 Uiso 1 1 calc R . .
C1A C 0.3314(2) 0.3370(6) 0.35867(14) 0.0210(7) Uani 1 1 d . . .
H1A H 0.2814 0.4576 0.3593 0.025 Uiso 1 1 calc R . .
C1B C 0.3211(2) 0.1286(6) 0.32741(13) 0.0192(7) Uani 1 1 d . . .
H1B H 0.2646 0.1073 0.3061 0.023 Uiso 1 1 calc R . .
C1C C 0.5734(2) -0.1079(6) 0.48281(12) 0.0138(7) Uani 1 1 d . . .
C1D C 0.4755(2) -0.0194(6) 0.35902(14) 0.0143(7) Uani 1 1 d . . .
H1D H 0.5241 -0.1435 0.3597 0.017 Uiso 1 1 calc R . .
C1E C 0.3933(2) -0.0483(6) 0.32725(12) 0.0188(7) Uani 1 1 d . . .
H1E H 0.3867 -0.1901 0.3054 0.023 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
S1 C12 1.640(3) . ?
S2 C1C 1.644(3) . ?
O1 C12 1.340(4) . ?
O1 C2 1.461(4) . ?
O2 C7 1.213(4) . ?
O3 C1C 1.328(4) . ?
O3 C15 1.465(4) . ?
O4 C17 1.210(4) . ?
C2 C4 1.507(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 N5 1.480(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C12 1.368(4) . ?
N5 C7 1.401(4) . ?
N6 C1C 1.376(4) . ?
N6 C17 1.408(4) . ?
N6 C16 1.467(4) . ?
C7 C8 1.497(4) . ?
C8 C13 1.385(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 C14 1.391(5) . ?
C11 H11 0.9500 . ?
C13 C14 1.388(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.515(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.492(4) . ?
C18 C1D 1.377(5) . ?
C18 C19 1.386(4) . ?
C19 C1A 1.381(5) . ?
C19 H19 0.9500 . ?
C1A C1B 1.384(5) . ?
C1A H1A 0.9500 . ?
C1B C1E 1.381(5) . ?
C1B H1B 0.9500 . ?
C1D C1E 1.392(4) . ?
C1D H1D 0.9500 . ?
C1E H1E 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
C12 O1 C2 110.2(2) . . ?
C1C O3 C15 110.2(2) . . ?
O1 C2 C4 104.3(2) . . ?
O1 C2 H2A 110.9 . . ?
C4 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C4 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N5 C4 C2 100.3(3) . . ?
N5 C4 H4A 111.7 . . ?
C2 C4 H4A 111.7 . . ?
N5 C4 H4B 111.7 . . ?
C2 C4 H4B 111.7 . . ?
H4A C4 H4B 109.5 . . ?
C12 N5 C7 128.6(3) . . ?
C12 N5 C4 110.4(3) . . ?
C7 N5 C4 118.4(3) . . ?
C1C N6 C17 127.8(3) . . ?
C1C N6 C16 110.4(3) . . ?
C17 N6 C16 118.8(3) . . ?
O2 C7 N5 119.5(3) . . ?
O2 C7 C8 121.9(3) . . ?
N5 C7 C8 118.4(3) . . ?
C13 C8 C9 120.7(3) . . ?
C13 C8 C7 119.2(3) . . ?
C9 C8 C7 119.7(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C14 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C14 C11 H11 119.7 . . ?
O1 C12 N5 109.1(3) . . ?
O1 C12 S1 120.6(2) . . ?
N5 C12 S1 130.3(2) . . ?
C8 C13 C14 120.0(3) . . ?
C8 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C11 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C11 C14 H14 120.4 . . ?
O3 C15 C16 104.0(2) . . ?
O3 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
O3 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
N6 C16 C15 100.4(3) . . ?
N6 C16 H16A 111.7 . . ?
C15 C16 H16A 111.7 . . ?
N6 C16 H16B 111.7 . . ?
C15 C16 H16B 111.7 . . ?
H16A C16 H16B 109.5 . . ?
O4 C17 N6 119.2(3) . . ?
O4 C17 C18 121.7(3) . . ?
N6 C17 C18 118.9(3) . . ?
C1D C18 C19 120.3(3) . . ?
C1D C18 C17 120.2(3) . . ?
C19 C18 C17 119.1(3) . . ?
C1A C19 C18 120.0(3) . . ?
C1A C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C1A C1B 120.0(3) . . ?
C19 C1A H1A 120.0 . . ?
C1B C1A H1A 120.0 . . ?
C1E C1B C1A 119.9(3) . . ?
C1E C1B H1B 120.1 . . ?
C1A C1B H1B 120.1 . . ?
O3 C1C N6 109.4(3) . . ?
O3 C1C S2 121.0(2) . . ?
N6 C1C S2 129.6(2) . . ?
C18 C1D C1E 119.6(3) . . ?
C18 C1D H1D 120.2 . . ?
C1E C1D H1D 120.2 . . ?
C1B C1E C1D 120.2(3) . . ?
C1B C1E H1E 119.9 . . ?
C1D C1E H1E 119.9 . . ?

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
C12 O1 C2 C4 16.7(3) . . . . ?
O1 C2 C4 N5 -22.3(3) . . . . ?
C2 C4 N5 C12 22.3(3) . . . . ?
C2 C4 N5 C7 -174.4(3) . . . . ?
C12 N5 C7 O2 148.6(3) . . . . ?
C4 N5 C7 O2 -11.3(4) . . . . ?
C12 N5 C7 C8 -36.0(4) . . . . ?
C4 N5 C7 C8 164.2(3) . . . . ?
O2 C7 C8 C13 -49.7(5) . . . . ?
N5 C7 C8 C13 135.0(3) . . . . ?
O2 C7 C8 C9 123.7(4) . . . . ?
N5 C7 C8 C9 -51.6(4) . . . . ?
C13 C8 C9 C10 2.0(5) . . . . ?
C7 C8 C9 C10 -171.2(3) . . . . ?
C8 C9 C10 C11 -2.7(5) . . . . ?
C9 C10 C11 C14 1.3(5) . . . . ?
C2 O1 C12 N5 -2.7(3) . . . . ?
C2 O1 C12 S1 179.5(2) . . . . ?
C7 N5 C12 O1 -174.4(3) . . . . ?
C4 N5 C12 O1 -13.2(3) . . . . ?
C7 N5 C12 S1 3.2(5) . . . . ?
C4 N5 C12 S1 164.4(3) . . . . ?
C9 C8 C13 C14 0.1(5) . . . . ?
C7 C8 C13 C14 173.4(3) . . . . ?
C8 C13 C14 C11 -1.5(5) . . . . ?
C10 C11 C14 C13 0.8(5) . . . . ?
C1C O3 C15 C16 17.3(3) . . . . ?
C1C N6 C16 C15 21.8(3) . . . . ?
C17 N6 C16 C15 -176.1(3) . . . . ?
O3 C15 C16 N6 -22.4(3) . . . . ?
C1C N6 C17 O4 146.1(3) . . . . ?
C16 N6 C17 O4 -12.5(4) . . . . ?
C1C N6 C17 C18 -40.1(4) . . . . ?
C16 N6 C17 C18 161.3(3) . . . . ?
O4 C17 C18 C1D 123.5(4) . . . . ?
N6 C17 C18 C1D -50.2(4) . . . . ?
O4 C17 C18 C19 -48.9(5) . . . . ?
N6 C17 C18 C19 137.4(3) . . . . ?
C1D C18 C19 C1A 1.2(5) . . . . ?
C17 C18 C19 C1A 173.5(3) . . . . ?
C18 C19 C1A C1B -2.1(5) . . . . ?
C19 C1A C1B C1E 1.0(5) . . . . ?
C15 O3 C1C N6 -3.7(3) . . . . ?
C15 O3 C1C S2 178.8(2) . . . . ?
C17 N6 C1C O3 -172.4(3) . . . . ?
C16 N6 C1C O3 -12.3(3) . . . . ?
C17 N6 C1C S2 4.8(5) . . . . ?
C16 N6 C1C S2 164.9(2) . . . . ?
C19 C18 C1D C1E 0.9(5) . . . . ?
C17 C18 C1D C1E -171.4(3) . . . . ?
C1A C1B C1E C1D 1.0(5) . . . . ?
C18 C1D C1E C1B -1.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.075
