# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_mo_70124a
_database_code_depnum_ccdc_archive 'CCDC 1529349'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N O4 S2'
_chemical_formula_weight         335.38

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      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                   7.6834(16)
_cell_length_b                   8.0281(17)
_cell_length_c                   12.554(3)
_cell_angle_alpha                85.471(3)
_cell_angle_beta                 73.420(3)
_cell_angle_gamma                74.044(3)
_cell_volume                     713.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2832
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5020
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3057
_reflns_number_gt                2612
_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. 
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1093P)²+0.2144P] 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         3057
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_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
S1 S 0.99096(9) 0.75594(8) 0.32470(5) 0.0198(2) Uani 1 1 d . . . . .
S2 S 1.24664(9) 0.21684(8) 0.08977(5) 0.0215(2) Uani 1 1 d . . . . .
N1 N 1.1239(3) 0.3816(3) 0.17841(19) 0.0238(5) Uani 1 1 d . . . . .
O1 O 1.4038(3) 0.1170(3) 0.12691(17) 0.0282(5) Uani 1 1 d . . . . .
O2 O 1.1229(3) 0.1255(3) 0.07071(18) 0.0317(5) Uani 1 1 d . . . . .
O3 O 1.0862(3) 0.6194(3) 0.38588(16) 0.0270(5) Uani 1 1 d . . . . .
O4 O 1.0203(3) 0.9252(3) 0.32544(17) 0.0285(5) Uani 1 1 d . . . . .
C1 C 1.1281(4) 0.5442(3) 0.1346(2) 0.0192(5) Uani 1 1 d . . . . .
C2 C 1.2366(4) 0.5262(3) 0.0158(2) 0.0194(5) Uani 1 1 d . . . . .
C3 C 1.2782(4) 0.6566(3) -0.0588(2) 0.0224(6) Uani 1 1 d . . . . .
H3 H 1.2309 0.7748 -0.0370 0.027 Uiso 1 1 calc R U . . .
C4 C 1.3905(4) 0.6101(4) -0.1659(2) 0.0247(6) Uani 1 1 d . . . . .
H4 H 1.4174 0.6984 -0.2180 0.030 Uiso 1 1 calc R U . . .
C5 C 1.4645(4) 0.4374(4) -0.1987(2) 0.0267(6) Uani 1 1 d . . . . .
H5 H 1.5413 0.4093 -0.2724 0.032 Uiso 1 1 calc R U . . .
C6 C 1.4267(4) 0.3058(4) -0.1242(2) 0.0251(6) Uani 1 1 d . . . . .
H6 H 1.4777 0.1872 -0.1448 0.030 Uiso 1 1 calc R U . . .
C7 C 1.3117(4) 0.3553(3) -0.0192(2) 0.0210(5) Uani 1 1 d . . . . .
C8 C 1.0020(4) 0.3402(4) 0.2833(2) 0.0292(6) Uani 1 1 d . . . . .
H8A H 1.0615 0.3384 0.3430 0.044 Uiso 1 1 calc R U . . .
H8B H 0.9817 0.2262 0.2778 0.044 Uiso 1 1 calc R U . . .
H8C H 0.8807 0.4281 0.2997 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0577(4) 0.7000(3) 0.1846(2) 0.0216(5) Uani 1 1 d . . . . .
H9 H 1.0415 0.7956 0.1353 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7464(4) 0.7800(3) 0.3776(2) 0.0190(5) Uani 1 1 d . . . . .
C11 C 0.6802(4) 0.6810(4) 0.4678(2) 0.0233(6) Uani 1 1 d . . . . .
H11 H 0.7651 0.5953 0.4984 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4870(4) 0.7101(4) 0.5122(2) 0.0285(6) Uani 1 1 d . . . . .
H12 H 0.4389 0.6447 0.5746 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3632(4) 0.8341(4) 0.4661(2) 0.0292(6) Uani 1 1 d . . . . .
H13 H 0.2312 0.8521 0.4968 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4311(4) 0.9312(4) 0.3759(2) 0.0289(6) Uani 1 1 d . . . . .
H14 H 0.3459 1.0156 0.3445 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6239(4) 0.9055(4) 0.3310(2) 0.0241(6) Uani 1 1 d . . . . .
H15 H 0.6716 0.9725 0.2695 0.029 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 O4 1.439(2) . ?
S1 O3 1.440(2) . ?
S1 C9 1.744(3) . ?
S1 C10 1.766(3) . ?
S2 O2 1.429(2) . ?
S2 O1 1.431(2) . ?
S2 N1 1.681(2) . ?
S2 C7 1.741(3) . ?
N1 C1 1.381(3) . ?
N1 C8 1.456(4) . ?
C1 C9 1.345(4) . ?
C1 C2 1.483(3) . ?
C2 C7 1.387(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.380(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.390(4) . ?
C13 C14 1.382(5) . ?
C14 C15 1.388(4) . ?

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 118.20(12) . . ?
O4 S1 C9 104.97(12) . . ?
O3 S1 C9 109.99(13) . . ?
O4 S1 C10 106.82(12) . . ?
O3 S1 C10 108.14(12) . . ?
C9 S1 C10 108.32(12) . . ?
O2 S2 O1 116.96(13) . . ?
O2 S2 N1 110.02(13) . . ?
O1 S2 N1 109.36(12) . . ?
O2 S2 C7 112.71(13) . . ?
O1 S2 C7 112.23(13) . . ?
N1 S2 C7 92.90(12) . . ?
C1 N1 C8 127.3(2) . . ?
C1 N1 S2 114.79(18) . . ?
C8 N1 S2 117.01(19) . . ?
C9 C1 N1 129.8(2) . . ?
C9 C1 C2 121.2(2) . . ?
N1 C1 C2 108.9(2) . . ?
C7 C2 C3 118.7(2) . . ?
C7 C2 C1 113.3(2) . . ?
C3 C2 C1 127.9(2) . . ?
C4 C3 C2 118.5(2) . . ?
C3 C4 C5 121.6(3) . . ?
C6 C5 C4 120.3(3) . . ?
C7 C6 C5 117.0(3) . . ?
C6 C7 C2 123.9(3) . . ?
C6 C7 S2 126.1(2) . . ?
C2 C7 S2 110.04(19) . . ?
C1 C9 S1 130.8(2) . . ?
C11 C10 C15 121.5(3) . . ?
C11 C10 S1 119.6(2) . . ?
C15 C10 S1 118.8(2) . . ?
C10 C11 C12 118.5(3) . . ?
C11 C12 C13 120.5(3) . . ?
C14 C13 C12 120.4(3) . . ?
C13 C14 C15 120.0(3) . . ?
C14 C15 C10 119.1(3) . . ?

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
O2 S2 N1 C1 -117.2(2) . . . . ?
O1 S2 N1 C1 113.1(2) . . . . ?
C7 S2 N1 C1 -1.7(2) . . . . ?
O2 S2 N1 C8 52.7(2) . . . . ?
O1 S2 N1 C8 -77.0(2) . . . . ?
C7 S2 N1 C8 168.2(2) . . . . ?
C8 N1 C1 C9 16.8(5) . . . . ?
S2 N1 C1 C9 -174.6(2) . . . . ?
C8 N1 C1 C2 -165.9(3) . . . . ?
S2 N1 C1 C2 2.8(3) . . . . ?
C9 C1 C2 C7 174.9(2) . . . . ?
N1 C1 C2 C7 -2.8(3) . . . . ?
C9 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 -178.7(3) . . . . ?
C7 C2 C3 C4 1.2(4) . . . . ?
C1 C2 C3 C4 176.9(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C2 -1.3(4) . . . . ?
C5 C6 C7 S2 -178.7(2) . . . . ?
C3 C2 C7 C6 0.2(4) . . . . ?
C1 C2 C7 C6 -176.2(2) . . . . ?
C3 C2 C7 S2 177.92(19) . . . . ?
C1 C2 C7 S2 1.6(3) . . . . ?
O2 S2 C7 C6 -69.2(3) . . . . ?
O1 S2 C7 C6 65.4(3) . . . . ?
N1 S2 C7 C6 177.7(2) . . . . ?
O2 S2 C7 C2 113.1(2) . . . . ?
O1 S2 C7 C2 -112.3(2) . . . . ?
N1 S2 C7 C2 0.0(2) . . . . ?
N1 C1 C9 S1 19.0(5) . . . . ?
C2 C1 C9 S1 -158.1(2) . . . . ?
O4 S1 C9 C1 151.1(3) . . . . ?
O3 S1 C9 C1 23.0(3) . . . . ?
C10 S1 C9 C1 -95.0(3) . . . . ?
O4 S1 C10 C11 -124.7(2) . . . . ?
O3 S1 C10 C11 3.5(3) . . . . ?
C9 S1 C10 C11 122.7(2) . . . . ?
O4 S1 C10 C15 51.8(2) . . . . ?
O3 S1 C10 C15 -180.0(2) . . . . ?
C9 S1 C10 C15 -60.8(2) . . . . ?
C15 C10 C11 C12 -0.5(4) . . . . ?
S1 C10 C11 C12 176.0(2) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
S1 C10 C15 C14 -176.7(2) . . . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.177



####################################################################### 
# 
# 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_mo_61219a
_database_code_depnum_ccdc_archive 'CCDC 1529348'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N O4 S2'
_chemical_formula_weight         335.38

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.151(10)
_cell_length_b                   8.239(9)
_cell_length_c                   22.94(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.06(2)
_cell_angle_gamma                90
_cell_volume                     1517(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1459
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.368
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9438
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2954
_reflns_number_gt                1580
_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. 
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1381P)²] 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         2954
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.1803
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.19022(16) 0.26668(13) 0.41772(6) 0.0571(4) Uani 1 1 d . . . . .
S2 S 0.34086(16) 0.74894(12) 0.28218(6) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.1773(4) 0.3440(4) 0.35148(16) 0.0528(10) Uani 1 1 d . . . . .
O1 O 0.0322(5) 0.2188(5) 0.4268(2) 0.1019(15) Uani 1 1 d . . . . .
O2 O 0.3162(5) 0.1488(4) 0.42778(17) 0.0834(12) Uani 1 1 d . . . . .
O3 O 0.2396(4) 0.8736(4) 0.30097(16) 0.0677(10) Uani 1 1 d . . . . .
O4 O 0.3523(6) 0.7447(4) 0.22067(16) 0.0795(12) Uani 1 1 d . . . . .
C1 C 0.2505(5) 0.4501(5) 0.4519(2) 0.0515(11) Uani 1 1 d . . . . .
C2 C 0.2732(6) 0.4821(6) 0.5102(2) 0.0674(14) Uani 1 1 d . . . . .
H2 H 0.2601 0.4007 0.5371 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3162(7) 0.6374(7) 0.5296(2) 0.0721(15) Uani 1 1 d . . . . .
H3 H 0.3341 0.6616 0.5699 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3321(6) 0.7552(6) 0.4889(2) 0.0622(13) Uani 1 1 d . . . . .
H4 H 0.3573 0.8606 0.5020 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3122(5) 0.7230(5) 0.4299(2) 0.0511(11) Uani 1 1 d . . . . .
H5 H 0.3261 0.8049 0.4033 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2704(5) 0.5652(4) 0.40956(19) 0.0416(10) Uani 1 1 d . . . . .
C7 C 0.2427(5) 0.4993(4) 0.34928(19) 0.0452(10) Uani 1 1 d . . . . .
C8 C 0.2675(5) 0.5603(5) 0.2971(2) 0.0500(11) Uani 1 1 d . . . . .
H8 H 0.2415 0.4912 0.2648 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5417(6) 0.7672(4) 0.3233(2) 0.0475(11) Uani 1 1 d . . . . .
C10 C 0.5917(6) 0.9121(5) 0.3502(2) 0.0640(14) Uani 1 1 d . . . . .
H10 H 0.5156 0.9959 0.3509 0.077 Uiso 1 1 calc R U . . .
C11 C 0.7547(7) 0.9317(7) 0.3760(3) 0.0825(17) Uani 1 1 d . . . . .
H11 H 0.7903 1.0309 0.3930 0.099 Uiso 1 1 calc R U . . .
C12 C 0.8647(7) 0.8088(9) 0.3770(3) 0.0881(18) Uani 1 1 d . . . . .
H12 H 0.9748 0.8232 0.3954 0.106 Uiso 1 1 calc R U . . .
C13 C 0.8151(7) 0.6636(9) 0.3513(3) 0.0795(16) Uani 1 1 d . . . . .
H13 H 0.8912 0.5790 0.3524 0.095 Uiso 1 1 calc R U . . .
C14 C 0.6536(6) 0.6421(6) 0.3238(2) 0.0607(13) Uani 1 1 d . . . . .
H14 H 0.6198 0.5438 0.3056 0.073 Uiso 1 1 calc R U . . .
C15 C 0.1364(7) 0.2389(5) 0.2997(2) 0.0697(15) Uani 1 1 d . . . . .
H15A H 0.0657 0.2965 0.2686 0.105 Uiso 1 1 calc R U . . .
H15B H 0.0795 0.1440 0.3100 0.105 Uiso 1 1 calc R U . . .
H15C H 0.2370 0.2072 0.2864 0.105 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 O1 1.398(4) . ?
S1 O2 1.403(4) . ?
S1 N1 1.634(4) . ?
S1 C1 1.734(4) . ?
S2 O3 1.430(3) . ?
S2 O4 1.431(4) . ?
S2 C8 1.721(4) . ?
S2 C9 1.747(5) . ?
N1 C7 1.391(5) . ?
N1 C15 1.461(6) . ?
C1 C2 1.343(7) . ?
C1 C6 1.387(6) . ?
C2 C3 1.380(7) . ?
C3 C4 1.368(7) . ?
C4 C5 1.362(7) . ?
C5 C6 1.402(5) . ?
C6 C7 1.466(6) . ?
C7 C8 1.345(6) . ?
C9 C10 1.373(6) . ?
C9 C14 1.375(6) . ?
C10 C11 1.366(7) . ?
C11 C12 1.350(8) . ?
C12 C13 1.364(9) . ?
C13 C14 1.368(7) . ?

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
O1 S1 O2 116.6(3) . . ?
O1 S1 N1 109.7(3) . . ?
O2 S1 N1 110.4(2) . . ?
O1 S1 C1 112.0(2) . . ?
O2 S1 C1 112.8(2) . . ?
N1 S1 C1 92.7(2) . . ?
O3 S2 O4 117.1(2) . . ?
O3 S2 C8 110.5(2) . . ?
O4 S2 C8 105.0(2) . . ?
O3 S2 C9 108.1(2) . . ?
O4 S2 C9 108.5(2) . . ?
C8 S2 C9 107.2(2) . . ?
C7 N1 C15 123.4(4) . . ?
C7 N1 S1 115.4(3) . . ?
C15 N1 S1 119.6(3) . . ?
C2 C1 C6 123.4(4) . . ?
C2 C1 S1 126.9(4) . . ?
C6 C1 S1 109.8(3) . . ?
C1 C2 C3 119.1(5) . . ?
C4 C3 C2 119.1(5) . . ?
C5 C4 C3 122.1(4) . . ?
C4 C5 C6 119.4(4) . . ?
C1 C6 C5 116.9(4) . . ?
C1 C6 C7 112.9(3) . . ?
C5 C6 C7 130.2(4) . . ?
C8 C7 N1 119.6(4) . . ?
C8 C7 C6 132.7(4) . . ?
N1 C7 C6 107.7(4) . . ?
C7 C8 S2 128.7(3) . . ?
C10 C9 C14 120.2(5) . . ?
C10 C9 S2 119.6(3) . . ?
C14 C9 S2 119.8(4) . . ?
C11 C10 C9 119.2(5) . . ?
C12 C11 C10 120.8(6) . . ?
C11 C12 C13 120.3(6) . . ?
C12 C13 C14 120.1(5) . . ?
C13 C14 C9 119.4(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
O1 S1 N1 C7 125.2(3) . . . . ?
O2 S1 N1 C7 -105.0(3) . . . . ?
C1 S1 N1 C7 10.6(3) . . . . ?
O1 S1 N1 C15 -68.7(4) . . . . ?
O2 S1 N1 C15 61.2(4) . . . . ?
C1 S1 N1 C15 176.8(4) . . . . ?
O1 S1 C1 C2 62.0(5) . . . . ?
O2 S1 C1 C2 -71.8(5) . . . . ?
N1 S1 C1 C2 174.6(4) . . . . ?
O1 S1 C1 C6 -116.9(4) . . . . ?
O2 S1 C1 C6 109.2(4) . . . . ?
N1 S1 C1 C6 -4.3(3) . . . . ?
C6 C1 C2 C3 1.0(8) . . . . ?
S1 C1 C2 C3 -177.8(4) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C2 C3 C4 C5 -2.2(8) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C2 C1 C6 C5 -1.7(7) . . . . ?
S1 C1 C6 C5 177.3(3) . . . . ?
C2 C1 C6 C7 178.5(4) . . . . ?
S1 C1 C6 C7 -2.5(4) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 -179.8(4) . . . . ?
C15 N1 C7 C8 1.5(6) . . . . ?
S1 N1 C7 C8 167.1(3) . . . . ?
C15 N1 C7 C6 -178.9(4) . . . . ?
S1 N1 C7 C6 -13.3(4) . . . . ?
C1 C6 C7 C8 -170.9(5) . . . . ?
C5 C6 C7 C8 9.4(8) . . . . ?
C1 C6 C7 N1 9.6(5) . . . . ?
C5 C6 C7 N1 -170.1(4) . . . . ?
N1 C7 C8 S2 178.1(3) . . . . ?
C6 C7 C8 S2 -1.4(7) . . . . ?
O3 S2 C8 C7 -56.6(5) . . . . ?
O4 S2 C8 C7 176.3(4) . . . . ?
C9 S2 C8 C7 61.0(5) . . . . ?
O3 S2 C9 C10 -20.9(5) . . . . ?
O4 S2 C9 C10 107.1(4) . . . . ?
C8 S2 C9 C10 -140.0(4) . . . . ?
O3 S2 C9 C14 165.4(4) . . . . ?
O4 S2 C9 C14 -66.7(4) . . . . ?
C8 S2 C9 C14 46.3(4) . . . . ?
C14 C9 C10 C11 1.8(8) . . . . ?
S2 C9 C10 C11 -172.0(4) . . . . ?
C9 C10 C11 C12 -2.3(9) . . . . ?
C10 C11 C12 C13 1.2(10) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
C12 C13 C14 C9 -1.1(8) . . . . ?
C10 C9 C14 C13 -0.1(7) . . . . ?
S2 C9 C14 C13 173.6(4) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.090



