# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_cd15151
_database_code_depnum_ccdc_archive 'CCDC 1450076'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O3 S'
_chemical_formula_weight         390.44

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'

_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                   9.4353(13)
_cell_length_b                   17.316(2)
_cell_length_c                   11.6428(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.321(3)
_cell_angle_gamma                90
_cell_volume                     1900.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2774
_cell_measurement_theta_min      4.705
_cell_measurement_theta_max      50.398

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11248
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         25.999
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3737
_reflns_number_gt                2885
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0661P)²+0.2201P] 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     SHELXL
_refine_ls_extinction_coef       0.0183(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.86566(5) 0.16819(3) 1.14682(4) 0.04708(19) Uani 1 1 d . . . . .
N1 N 0.71579(16) 0.18346(9) 0.89104(12) 0.0428(4) Uani 1 1 d . . . . .
N2 N 0.71285(16) 0.20797(9) 1.09901(12) 0.0437(4) Uani 1 1 d . . . . .
O1 O 0.51680(13) 0.11521(7) 0.86848(10) 0.0402(3) Uani 1 1 d . . . . .
O2 O 0.84485(18) 0.08730(9) 1.13789(15) 0.0720(5) Uani 1 1 d . . . . .
O3 O 0.90120(17) 0.20210(10) 1.25570(12) 0.0698(5) Uani 1 1 d . . . . .
C1 C 0.6524(2) 0.17514(10) 0.99568(15) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.53155(19) 0.13342(10) 0.98394(15) 0.0383(4) Uani 1 1 d . . . . .
C3 C 0.6311(2) 0.14670(11) 0.81871(15) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.6454(2) 0.13696(10) 0.69589(15) 0.0399(4) Uani 1 1 d . . . . .
C5 C 0.7638(2) 0.16627(13) 0.64372(17) 0.0529(5) Uani 1 1 d . . . . .
H5 H 0.8346 0.1907 0.6882 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7774(2) 0.15948(15) 0.52655(18) 0.0626(6) Uani 1 1 d . . . . .
H6 H 0.8567 0.1796 0.4922 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6731(3) 0.12272(13) 0.46052(18) 0.0608(6) Uani 1 1 d . . . . .
H7 H 0.6822 0.1178 0.3816 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5559(3) 0.09339(12) 0.51130(18) 0.0574(6) Uani 1 1 d . . . . .
H8 H 0.4859 0.0687 0.4664 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5409(2) 0.10016(11) 0.62861(16) 0.0488(5) Uani 1 1 d . . . . .
H9 H 0.4611 0.0801 0.6623 0.059 Uiso 1 1 calc R U . . .
C10 C 0.42439(19) 0.10463(11) 1.05886(15) 0.0409(4) Uani 1 1 d . . . . .
C11 C 0.3271(2) 0.04898(11) 1.02158(18) 0.0474(5) Uani 1 1 d . . . . .
H11 H 0.3302 0.0297 0.9472 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2259(2) 0.02205(13) 1.0940(2) 0.0588(6) Uani 1 1 d . . . . .
H12 H 0.1606 -0.0148 1.0676 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2207(2) 0.04896(15) 1.2041(2) 0.0674(7) Uani 1 1 d . . . . .
H13 H 0.1524 0.0305 1.2525 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3170(3) 0.10359(17) 1.2427(2) 0.0720(7) Uani 1 1 d . . . . .
H14 H 0.3141 0.1218 1.3177 0.086 Uiso 1 1 calc R U . . .
C15 C 0.4177(2) 0.13157(14) 1.17133(18) 0.0594(6) Uani 1 1 d . . . . .
H15 H 0.4819 0.1688 1.1983 0.071 Uiso 1 1 calc R U . . .
C16 C 0.68601(19) 0.28957(12) 1.11998(16) 0.0437(5) Uani 1 1 d . . . . .
C17 C 0.6703(2) 0.31549(14) 1.23096(18) 0.0575(6) Uani 1 1 d . . . . .
H17 H 0.6780 0.2813 1.2925 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6429(2) 0.39287(15) 1.2495(2) 0.0671(7) Uani 1 1 d . . . . .
H18 H 0.6325 0.4106 1.3241 0.081 Uiso 1 1 calc R U . . .
C19 C 0.6307(2) 0.44388(15) 1.1596(2) 0.0671(7) Uani 1 1 d . . . . .
H19 H 0.6145 0.4960 1.1731 0.081 Uiso 1 1 calc R U . . .
C20 C 0.6428(3) 0.41730(14) 1.0494(2) 0.0657(6) Uani 1 1 d . . . . .
H20 H 0.6323 0.4514 0.9879 0.079 Uiso 1 1 calc R U . . .
C21 C 0.6704(2) 0.34025(12) 1.02900(18) 0.0526(5) Uani 1 1 d . . . . .
H21 H 0.6784 0.3226 0.9541 0.063 Uiso 1 1 calc R U . . .
C22 C 0.9939(2) 0.19593(13) 1.05049(18) 0.0530(5) Uani 1 1 d . . . . .
H22A H 1.0854 0.1780 1.0780 0.079 Uiso 1 1 calc R U . . .
H22B H 0.9952 0.2512 1.0443 0.079 Uiso 1 1 calc R U . . .
H22C H 0.9715 0.1738 0.9764 0.079 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 O2 1.4177(16) . ?
S1 O3 1.4247(15) . ?
S1 N2 1.6728(16) . ?
S1 C22 1.750(2) . ?
N1 C3 1.303(2) . ?
N1 C1 1.386(2) . ?
N2 C1 1.428(2) . ?
N2 C16 1.458(3) . ?
O1 C3 1.359(2) . ?
O1 C2 1.382(2) . ?
C1 C2 1.352(3) . ?
C2 C10 1.450(3) . ?
C3 C4 1.452(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.389(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.388(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.379(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O2 S1 O3 119.97(10) . . ?
O2 S1 N2 105.52(9) . . ?
O3 S1 N2 107.15(9) . . ?
O2 S1 C22 108.75(11) . . ?
O3 S1 C22 108.25(10) . . ?
N2 S1 C22 106.42(9) . . ?
C3 N1 C1 104.00(15) . . ?
C1 N2 C16 117.43(14) . . ?
C1 N2 S1 115.20(13) . . ?
C16 N2 S1 119.78(11) . . ?
C3 O1 C2 105.83(13) . . ?
C2 C1 N1 111.02(15) . . ?
C2 C1 N2 127.18(17) . . ?
N1 C1 N2 121.79(16) . . ?
C1 C2 O1 105.76(16) . . ?
C1 C2 C10 136.76(17) . . ?
O1 C2 C10 117.47(15) . . ?
N1 C3 O1 113.39(16) . . ?
N1 C3 C4 127.90(18) . . ?
O1 C3 C4 118.72(16) . . ?
C5 C4 C9 119.10(18) . . ?
C5 C4 C3 119.79(17) . . ?
C9 C4 C3 121.10(18) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C11 C10 C15 118.15(19) . . ?
C11 C10 C2 121.25(17) . . ?
C15 C10 C2 120.60(18) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C21 C16 C17 120.0(2) . . ?
C21 C16 N2 120.14(17) . . ?
C17 C16 N2 119.84(18) . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 119.9(2) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 S1 N2 C1 -44.82(16) . . . . ?
O3 S1 N2 C1 -173.74(14) . . . . ?
C22 S1 N2 C1 70.63(15) . . . . ?
O2 S1 N2 C16 166.32(15) . . . . ?
O3 S1 N2 C16 37.40(17) . . . . ?
C22 S1 N2 C16 -78.23(16) . . . . ?
C3 N1 C1 C2 0.2(2) . . . . ?
C3 N1 C1 N2 -179.76(16) . . . . ?
C16 N2 C1 C2 -98.5(2) . . . . ?
S1 N2 C1 C2 111.85(19) . . . . ?
C16 N2 C1 N1 81.4(2) . . . . ?
S1 N2 C1 N1 -68.2(2) . . . . ?
N1 C1 C2 O1 -0.5(2) . . . . ?
N2 C1 C2 O1 179.45(16) . . . . ?
N1 C1 C2 C10 178.1(2) . . . . ?
N2 C1 C2 C10 -1.9(4) . . . . ?
C3 O1 C2 C1 0.60(19) . . . . ?
C3 O1 C2 C10 -178.34(15) . . . . ?
C1 N1 C3 O1 0.2(2) . . . . ?
C1 N1 C3 C4 179.73(18) . . . . ?
C2 O1 C3 N1 -0.5(2) . . . . ?
C2 O1 C3 C4 179.90(15) . . . . ?
N1 C3 C4 C5 2.7(3) . . . . ?
O1 C3 C4 C5 -177.74(16) . . . . ?
N1 C3 C4 C9 -175.82(19) . . . . ?
O1 C3 C4 C9 3.7(3) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C6 -178.17(19) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C3 C4 C9 C8 178.44(18) . . . . ?
C1 C2 C10 C11 -166.2(2) . . . . ?
O1 C2 C10 C11 12.3(3) . . . . ?
C1 C2 C10 C15 12.9(3) . . . . ?
O1 C2 C10 C15 -168.57(17) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C2 C10 C11 C12 179.89(18) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C2 C10 C15 C14 -179.3(2) . . . . ?
C1 N2 C16 C21 -31.9(3) . . . . ?
S1 N2 C16 C21 116.28(18) . . . . ?
C1 N2 C16 C17 145.36(19) . . . . ?
S1 N2 C16 C17 -66.5(2) . . . . ?
C21 C16 C17 C18 -1.8(3) . . . . ?
N2 C16 C17 C18 -179.10(18) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 1.5(4) . . . . ?
C18 C19 C20 C21 -1.6(4) . . . . ?
C17 C16 C21 C20 1.8(3) . . . . ?
N2 C16 C21 C20 179.02(18) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22C N1 0.96 2.58 3.160(2) 119.3 .
C21 H21 N1 0.93 2.55 3.192(3) 126.8 .
C21 H21 N1 0.93 2.55 3.192(3) 126.8 .

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16075
_database_code_depnum_ccdc_archive 'CCDC 1455246'
_audit_update_record             
;
2016-02-23 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O3 S2'
_chemical_formula_weight         434.51

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                   18.929(9)
_cell_length_b                   12.430(6)
_cell_length_c                   8.472(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.235(13)
_cell_angle_gamma                90
_cell_volume                     1992.9(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1157
_cell_measurement_theta_min      5.411
_cell_measurement_theta_max      38.774

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11203
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3705
_reflns_number_gt                2463
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0451P)²+0.7329P] 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         3705
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001

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 0.42315(4) 0.89888(7) 0.18802(10) 0.0485(3) Uani 1 1 d . . . . .
S2 S 0.15486(4) 1.07280(7) 0.20613(10) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.24137(12) 1.05950(18) 0.1780(3) 0.0366(6) Uani 1 1 d . . . . .
N2 N 0.24918(13) 0.8652(2) 0.2384(3) 0.0373(6) Uani 1 1 d . . . . .
O1 O 0.20947(12) 0.74794(18) 0.4206(3) 0.0532(6) Uani 1 1 d . . . . .
O2 O 0.13844(12) 1.00700(19) 0.3382(3) 0.0566(7) Uani 1 1 d . . . . .
O3 O 0.14212(12) 1.18576(18) 0.2116(3) 0.0575(6) Uani 1 1 d . . . . .
C1 C 0.28747(16) 1.1390(2) 0.1208(3) 0.0359(7) Uani 1 1 d . . . . .
C2 C 0.27463(19) 1.2441(3) 0.0683(4) 0.0495(9) Uani 1 1 d . . . . .
H2 H 0.2295 1.2737 0.0694 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3311(2) 1.3016(3) 0.0153(4) 0.0544(9) Uani 1 1 d . . . . .
H3 H 0.3240 1.3712 -0.0217 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3985(2) 1.2587(3) 0.0153(4) 0.0595(10) Uani 1 1 d . . . . .
H4 H 0.4356 1.3001 -0.0214 0.071 Uiso 1 1 calc R U . . .
C5 C 0.41195(18) 1.1556(3) 0.0688(4) 0.0480(9) Uani 1 1 d . . . . .
H5 H 0.4575 1.1276 0.0703 0.058 Uiso 1 1 calc R U . . .
C6 C 0.35487(16) 1.0948(2) 0.1206(3) 0.0364(7) Uani 1 1 d . . . . .
C7 C 0.35010(15) 0.9839(2) 0.1701(3) 0.0347(7) Uani 1 1 d . . . . .
C8 C 0.28177(15) 0.9630(2) 0.1986(3) 0.0336(7) Uani 1 1 d . . . . .
C9 C 0.24704(16) 0.8245(2) 0.3877(4) 0.0377(7) Uani 1 1 d . . . . .
C10 C 0.29549(15) 0.8767(2) 0.5074(3) 0.0346(7) Uani 1 1 d . . . . .
C11 C 0.36859(16) 0.8729(2) 0.4908(3) 0.0353(7) Uani 1 1 d . . . . .
C12 C 0.40029(16) 0.8128(2) 0.3548(4) 0.0431(8) Uani 1 1 d . . . . .
H12A H 0.3670 0.7586 0.3181 0.052 Uiso 1 1 calc R U . . .
H12B H 0.4426 0.7760 0.3923 0.052 Uiso 1 1 calc R U . . .
C13 C 0.26716(18) 0.9242(2) 0.6398(4) 0.0440(8) Uani 1 1 d . . . . .
H13 H 0.2185 0.9234 0.6530 0.053 Uiso 1 1 calc R U . . .
C14 C 0.31023(19) 0.9727(3) 0.7524(4) 0.0513(9) Uani 1 1 d . . . . .
H14 H 0.2908 1.0050 0.8403 0.062 Uiso 1 1 calc R U . . .
C15 C 0.38254(19) 0.9727(3) 0.7333(4) 0.0499(9) Uani 1 1 d . . . . .
H15 H 0.4119 1.0067 0.8073 0.060 Uiso 1 1 calc R U . . .
C16 C 0.41127(17) 0.9223(2) 0.6046(4) 0.0432(8) Uani 1 1 d . . . . .
H16 H 0.4601 0.9214 0.5939 0.052 Uiso 1 1 calc R U . . .
C17 C 0.11599(15) 1.0190(2) 0.0335(4) 0.0374(7) Uani 1 1 d . . . . .
C18 C 0.08295(17) 0.9204(3) 0.0379(4) 0.0483(9) Uani 1 1 d . . . . .
H18 H 0.0794 0.8832 0.1327 0.058 Uiso 1 1 calc R U . . .
C19 C 0.05536(17) 0.8778(3) -0.0997(4) 0.0504(9) Uani 1 1 d . . . . .
H19 H 0.0321 0.8120 -0.0963 0.060 Uiso 1 1 calc R U . . .
C20 C 0.06101(16) 0.9296(3) -0.2429(4) 0.0441(8) Uani 1 1 d . . . . .
C21 C 0.09300(17) 1.0297(3) -0.2433(4) 0.0494(9) Uani 1 1 d . . . . .
H21 H 0.0960 1.0672 -0.3379 0.059 Uiso 1 1 calc R U . . .
C22 C 0.12040(17) 1.0749(3) -0.1073(4) 0.0494(9) Uani 1 1 d . . . . .
H22 H 0.1417 1.1423 -0.1098 0.059 Uiso 1 1 calc R U . . .
C23 C 0.0354(2) 0.8763(3) -0.3931(5) 0.0660(11) Uani 1 1 d . . . . .
H23A H 0.0742 0.8405 -0.4419 0.099 Uiso 1 1 calc R U . . .
H23B H 0.0163 0.9297 -0.4638 0.099 Uiso 1 1 calc R U . . .
H23C H -0.0006 0.8247 -0.3693 0.099 Uiso 1 1 calc R U . . .
H2A H 0.2301(16) 0.831(3) 0.162(4) 0.047(10) 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
S1 C7 1.744(3) . ?
S1 C12 1.831(3) . ?
S2 O2 1.426(2) . ?
S2 O3 1.426(2) . ?
S2 N1 1.668(3) . ?
S2 C17 1.755(3) . ?
N1 C1 1.412(4) . ?
N1 C8 1.431(4) . ?
N2 C9 1.364(4) . ?
N2 C8 1.408(4) . ?
N2 H2A 0.85(3) . ?
O1 C9 1.224(3) . ?
C1 C6 1.389(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(4) . ?
C7 C8 1.346(4) . ?
C9 C10 1.500(4) . ?
C10 C13 1.386(4) . ?
C10 C11 1.395(4) . ?
C11 C16 1.388(4) . ?
C11 C12 1.508(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.376(4) . ?
C17 C22 1.385(4) . ?
C18 C19 1.374(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(4) . ?
C20 C23 1.505(5) . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C7 S1 C12 102.77(14) . . ?
O2 S2 O3 119.98(15) . . ?
O2 S2 N1 106.65(13) . . ?
O3 S2 N1 105.64(13) . . ?
O2 S2 C17 109.90(15) . . ?
O3 S2 C17 109.53(15) . . ?
N1 S2 C17 103.80(13) . . ?
C1 N1 C8 107.2(2) . . ?
C1 N1 S2 126.6(2) . . ?
C8 N1 S2 126.12(19) . . ?
C9 N2 C8 124.4(3) . . ?
C9 N2 H2A 120(2) . . ?
C8 N2 H2A 116(2) . . ?
C6 C1 C2 121.5(3) . . ?
C6 C1 N1 107.3(3) . . ?
C2 C1 N1 131.2(3) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 C7 108.3(3) . . ?
C5 C6 C7 131.4(3) . . ?
C8 C7 C6 107.6(3) . . ?
C8 C7 S1 129.1(2) . . ?
C6 C7 S1 123.3(2) . . ?
C7 C8 N2 129.6(3) . . ?
C7 C8 N1 109.2(2) . . ?
N2 C8 N1 121.2(2) . . ?
O1 C9 N2 121.9(3) . . ?
O1 C9 C10 122.2(3) . . ?
N2 C9 C10 115.9(3) . . ?
C13 C10 C11 119.9(3) . . ?
C13 C10 C9 119.3(3) . . ?
C11 C10 C9 120.7(3) . . ?
C16 C11 C10 118.6(3) . . ?
C16 C11 C12 121.0(3) . . ?
C10 C11 C12 120.4(3) . . ?
C11 C12 S1 113.9(2) . . ?
C11 C12 H12A 108.8 . . ?
S1 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
S1 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C10 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C22 120.4(3) . . ?
C18 C17 S2 120.0(3) . . ?
C22 C17 S2 119.6(2) . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C21 117.6(3) . . ?
C19 C20 C23 120.6(3) . . ?
C21 C20 C23 121.8(3) . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
C17 C22 H22 120.4 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O2 S2 N1 C1 -147.3(2) . . . . ?
O3 S2 N1 C1 -18.6(3) . . . . ?
C17 S2 N1 C1 96.6(3) . . . . ?
O2 S2 N1 C8 36.7(3) . . . . ?
O3 S2 N1 C8 165.5(2) . . . . ?
C17 S2 N1 C8 -79.3(3) . . . . ?
C8 N1 C1 C6 -5.2(3) . . . . ?
S2 N1 C1 C6 178.2(2) . . . . ?
C8 N1 C1 C2 173.8(3) . . . . ?
S2 N1 C1 C2 -2.8(5) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
N1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
N1 C1 C6 C5 179.8(3) . . . . ?
C2 C1 C6 C7 -175.9(3) . . . . ?
N1 C1 C6 C7 3.2(3) . . . . ?
C4 C5 C6 C1 -1.5(5) . . . . ?
C4 C5 C6 C7 174.2(3) . . . . ?
C1 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C8 -176.0(3) . . . . ?
C1 C6 C7 S1 -179.3(2) . . . . ?
C5 C6 C7 S1 4.6(5) . . . . ?
C12 S1 C7 C8 -33.1(3) . . . . ?
C12 S1 C7 C6 146.2(2) . . . . ?
C6 C7 C8 N2 174.9(3) . . . . ?
S1 C7 C8 N2 -5.7(5) . . . . ?
C6 C7 C8 N1 -3.4(3) . . . . ?
S1 C7 C8 N1 176.0(2) . . . . ?
C9 N2 C8 C7 83.3(4) . . . . ?
C9 N2 C8 N1 -98.5(3) . . . . ?
C1 N1 C8 C7 5.4(3) . . . . ?
S2 N1 C8 C7 -178.0(2) . . . . ?
C1 N1 C8 N2 -173.1(2) . . . . ?
S2 N1 C8 N2 3.5(4) . . . . ?
C8 N2 C9 O1 168.9(3) . . . . ?
C8 N2 C9 C10 -13.3(4) . . . . ?
O1 C9 C10 C13 -61.6(4) . . . . ?
N2 C9 C10 C13 120.6(3) . . . . ?
O1 C9 C10 C11 114.9(3) . . . . ?
N2 C9 C10 C11 -62.9(4) . . . . ?
C13 C10 C11 C16 -3.4(4) . . . . ?
C9 C10 C11 C16 -179.9(3) . . . . ?
C13 C10 C11 C12 174.5(3) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C16 C11 C12 S1 -84.5(3) . . . . ?
C10 C11 C12 S1 97.6(3) . . . . ?
C7 S1 C12 C11 -43.2(3) . . . . ?
C11 C10 C13 C14 3.2(5) . . . . ?
C9 C10 C13 C14 179.8(3) . . . . ?
C10 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C14 C15 C16 C11 1.3(5) . . . . ?
C10 C11 C16 C15 1.2(4) . . . . ?
C12 C11 C16 C15 -176.8(3) . . . . ?
O2 S2 C17 C18 -6.8(3) . . . . ?
O3 S2 C17 C18 -140.7(3) . . . . ?
N1 S2 C17 C18 106.9(3) . . . . ?
O2 S2 C17 C22 174.8(2) . . . . ?
O3 S2 C17 C22 41.0(3) . . . . ?
N1 S2 C17 C22 -71.4(3) . . . . ?
C22 C17 C18 C19 0.9(5) . . . . ?
S2 C17 C18 C19 -177.4(2) . . . . ?
C17 C18 C19 C20 1.4(5) . . . . ?
C18 C19 C20 C21 -2.9(5) . . . . ?
C18 C19 C20 C23 174.9(3) . . . . ?
C19 C20 C21 C22 2.1(5) . . . . ?
C23 C20 C21 C22 -175.7(3) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
C18 C17 C22 C21 -1.6(5) . . . . ?
S2 C17 C22 C21 176.7(2) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd15206
_database_code_depnum_ccdc_archive 'CCDC 1455247'
_audit_update_record             
;
2016-02-23 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H36 Au F6 N3 O4 S2'
_chemical_formula_weight         865.69

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'
F F 0.0171 0.0103 '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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   11.4418(8)
_cell_length_b                   11.4418(8)
_cell_length_c                   23.880(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2707.4(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5319
_cell_measurement_theta_min      4.451
_cell_measurement_theta_max      45.740

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.257
_shelx_estimated_absorpt_T_min   0.515
_shelx_estimated_absorpt_T_max   0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3224
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16240
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         25.955
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3549
_reflns_number_gt                3318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     1.000
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0247P)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_abs_structure_details 
; 
 Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.002(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3549
_refine_ls_number_parameters     209
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.045
_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
Au1 Au 0.19306(3) 0.19306(3) 0.0000 0.03840(11) Uani 1 2 d S T P . .
S1 S 0.01245(19) -0.13029(18) -0.00563(9) 0.0635(5) Uani 1 1 d . . . . .
F1 F 0.1118(11) -0.0575(11) -0.1043(3) 0.191(4) Uani 1 1 d . U . . .
F2 F -0.1014(10) -0.1662(10) -0.1026(3) 0.170(3) Uani 1 1 d . U . . .
F3 F 0.0059(9) -0.2661(9) -0.0935(4) 0.163(3) Uani 1 1 d . U . . .
N1 N 0.4657(5) 0.4092(5) 0.0380(2) 0.0375(12) Uani 1 1 d . . . . .
N2 N 0.0090(6) 0.0090(6) 0.0000 0.049(2) Uani 1 2 d S T P . .
O1 O 0.1404(6) -0.1048(7) 0.0111(3) 0.096(2) Uani 1 1 d . . . . .
O2 O -0.1040(7) -0.2424(6) 0.0155(3) 0.102(2) Uani 1 1 d . . . . .
C1 C 0.3661(6) 0.3661(6) 0.0000 0.0298(18) Uani 1 2 d S T P . .
C2 C 0.5710(8) 0.5365(6) 0.0230(3) 0.0489(16) Uani 1 1 d . . . . .
H2 H 0.6514 0.5873 0.0424 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4639(5) 0.3333(6) 0.0863(2) 0.0389(11) Uani 1 1 d . . . . .
C4 C 0.5077(7) 0.2389(6) 0.0801(3) 0.0469(15) Uani 1 1 d . . . . .
C5 C 0.5070(8) 0.1712(7) 0.1283(3) 0.065(2) Uani 1 1 d . . . . .
H5 H 0.5358 0.1084 0.1262 0.078 Uiso 1 1 calc R U . . .
C6 C 0.4658(10) 0.1932(8) 0.1782(4) 0.075(2) Uani 1 1 d . . . . .
H6 H 0.4686 0.1472 0.2098 0.090 Uiso 1 1 calc R U . . .
C7 C 0.4200(8) 0.2830(8) 0.1825(3) 0.069(2) Uani 1 1 d . . . . .
H7 H 0.3892 0.2948 0.2169 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4187(7) 0.3563(7) 0.1368(3) 0.0493(16) Uani 1 1 d . . . . .
C9 C 0.3736(9) 0.4615(9) 0.1416(3) 0.065(2) Uani 1 1 d . . . . .
H9 H 0.3631 0.4867 0.1034 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4803(13) 0.5881(12) 0.1705(6) 0.144(6) Uani 1 1 d . . . . .
H10A H 0.4484 0.6510 0.1743 0.216 Uiso 1 1 calc R U . . .
H10B H 0.5615 0.6282 0.1485 0.216 Uiso 1 1 calc R U . . .
H10C H 0.4985 0.5653 0.2069 0.216 Uiso 1 1 calc R U . . .
C11 C 0.2403(14) 0.4056(15) 0.1700(6) 0.147(6) Uani 1 1 d . U . . .
H11A H 0.2462 0.3762 0.2070 0.221 Uiso 1 1 calc R U . . .
H11B H 0.1733 0.3305 0.1489 0.221 Uiso 1 1 calc R U . . .
H11C H 0.2156 0.4742 0.1724 0.221 Uiso 1 1 calc R U . . .
C12 C 0.5545(9) 0.2145(9) 0.0243(3) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.5157 0.2468 -0.0042 0.073 Uiso 1 1 calc R U . . .
C13 C 0.5018(10) 0.0685(10) 0.0113(5) 0.099(4) Uani 1 1 d . . . . .
H13A H 0.5454 0.0341 0.0351 0.149 Uiso 1 1 calc R U . . .
H13B H 0.5202 0.0592 -0.0272 0.149 Uiso 1 1 calc R U . . .
H13C H 0.4062 0.0187 0.0177 0.149 Uiso 1 1 calc R U . . .
C14 C 0.7063(10) 0.3000(11) 0.0176(5) 0.106(4) Uani 1 1 d . . . . .
H14A H 0.7331 0.3936 0.0214 0.158 Uiso 1 1 calc R U . . .
H14B H 0.7319 0.2846 -0.0188 0.158 Uiso 1 1 calc R U . . .
H14C H 0.7500 0.2757 0.0459 0.158 Uiso 1 1 calc R U . . .
C15 C 0.0076(14) -0.1546(11) -0.0813(5) 0.109(4) Uani 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
Au1 C1 1.980(7) . ?
Au1 N2 2.106(7) . ?
S1 O1 1.401(6) . ?
S1 O2 1.402(6) . ?
S1 N2 1.620(4) . ?
S1 C15 1.825(12) . ?
F1 C15 1.277(13) . ?
F2 C15 1.292(13) . ?
F3 C15 1.299(12) . ?
N1 C1 1.343(6) . ?
N1 C2 1.396(8) . ?
N1 C3 1.438(7) . ?
N2 S1 1.620(4) 4 ?
C1 N1 1.343(6) 4 ?
C2 C2 1.292(14) 4 ?
C2 H2 0.9300 . ?
C3 C8 1.387(8) . ?
C3 C4 1.407(8) . ?
C4 C5 1.384(9) . ?
C4 C12 1.515(9) . ?
C5 C6 1.352(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.533(9) . ?
C9 C11 1.489(14) . ?
C9 C10 1.516(12) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.497(12) . ?
C12 C14 1.517(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 Au1 N2 180.00(3) . . ?
O1 S1 O2 120.2(5) . . ?
O1 S1 N2 108.0(4) . . ?
O2 S1 N2 113.1(4) . . ?
O1 S1 C15 105.2(6) . . ?
O2 S1 C15 105.9(5) . . ?
N2 S1 C15 102.6(4) . . ?
C1 N1 C2 109.9(5) . . ?
C1 N1 C3 124.6(5) . . ?
C2 N1 C3 125.5(5) . . ?
S1 N2 S1 122.6(5) . 4 ?
S1 N2 Au1 118.7(2) . . ?
S1 N2 Au1 118.7(2) 4 . ?
N1 C1 N1 105.2(6) 4 . ?
N1 C1 Au1 127.4(3) 4 . ?
N1 C1 Au1 127.4(3) . . ?
C2 C2 N1 107.5(4) 4 . ?
C2 C2 H2 126.2 4 . ?
N1 C2 H2 126.2 . . ?
C8 C3 C4 123.2(5) . . ?
C8 C3 N1 118.4(5) . . ?
C4 C3 N1 118.4(5) . . ?
C5 C4 C3 115.9(6) . . ?
C5 C4 C12 122.1(6) . . ?
C3 C4 C12 121.9(6) . . ?
C6 C5 C4 122.3(7) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.3(7) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 121.3(7) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 117.0(6) . . ?
C7 C8 C9 121.9(6) . . ?
C3 C8 C9 121.2(6) . . ?
C11 C9 C10 111.4(9) . . ?
C11 C9 C8 111.8(8) . . ?
C10 C9 C8 110.9(7) . . ?
C11 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C4 113.9(7) . . ?
C13 C12 C14 112.9(7) . . ?
C4 C12 C14 111.7(7) . . ?
C13 C12 H12 105.8 . . ?
C4 C12 H12 105.8 . . ?
C14 C12 H12 105.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F2 110.6(13) . . ?
F1 C15 F3 107.9(12) . . ?
F2 C15 F3 105.7(10) . . ?
F1 C15 S1 110.4(8) . . ?
F2 C15 S1 111.1(9) . . ?
F3 C15 S1 110.9(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
O1 S1 N2 S1 -158.2(4) . . . 4 ?
O2 S1 N2 S1 -22.7(4) . . . 4 ?
C15 S1 N2 S1 90.9(5) . . . 4 ?
O1 S1 N2 Au1 21.8(4) . . . . ?
O2 S1 N2 Au1 157.3(4) . . . . ?
C15 S1 N2 Au1 -89.1(5) . . . . ?
C2 N1 C1 N1 -0.2(4) . . . 4 ?
C3 N1 C1 N1 -179.0(6) . . . 4 ?
C2 N1 C1 Au1 179.8(4) . . . . ?
C3 N1 C1 Au1 1.0(6) . . . . ?
C1 N1 C2 C2 0.4(10) . . . 4 ?
C3 N1 C2 C2 179.3(7) . . . 4 ?
C1 N1 C3 C8 -94.6(6) . . . . ?
C2 N1 C3 C8 86.7(8) . . . . ?
C1 N1 C3 C4 85.1(6) . . . . ?
C2 N1 C3 C4 -93.5(7) . . . . ?
C8 C3 C4 C5 -1.8(9) . . . . ?
N1 C3 C4 C5 178.5(6) . . . . ?
C8 C3 C4 C12 179.0(6) . . . . ?
N1 C3 C4 C12 -0.7(9) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
C12 C4 C5 C6 179.7(8) . . . . ?
C4 C5 C6 C7 1.4(14) . . . . ?
C5 C6 C7 C8 -2.1(14) . . . . ?
C6 C7 C8 C3 0.9(12) . . . . ?
C6 C7 C8 C9 -177.3(8) . . . . ?
C4 C3 C8 C7 1.1(10) . . . . ?
N1 C3 C8 C7 -179.1(6) . . . . ?
C4 C3 C8 C9 179.3(7) . . . . ?
N1 C3 C8 C9 -1.0(10) . . . . ?
C7 C8 C9 C11 -50.9(12) . . . . ?
C3 C8 C9 C11 131.0(8) . . . . ?
C7 C8 C9 C10 74.1(11) . . . . ?
C3 C8 C9 C10 -104.0(9) . . . . ?
C5 C4 C12 C13 44.2(10) . . . . ?
C3 C4 C12 C13 -136.7(7) . . . . ?
C5 C4 C12 C14 -85.3(9) . . . . ?
C3 C4 C12 C14 93.8(9) . . . . ?
O1 S1 C15 F1 -50.7(11) . . . . ?
O2 S1 C15 F1 -179.0(10) . . . . ?
N2 S1 C15 F1 62.2(11) . . . . ?
O1 S1 C15 F2 -173.8(9) . . . . ?
O2 S1 C15 F2 57.9(10) . . . . ?
N2 S1 C15 F2 -60.9(10) . . . . ?
O1 S1 C15 F3 68.9(10) . . . . ?
O2 S1 C15 F3 -59.4(11) . . . . ?
N2 S1 C15 F3 -178.2(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
C2 H2 O2 0.93 2.57 3.294(9) 135.3 1_665

_refine_diff_density_max         0.969
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

