# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_OT617j_producteverd
_database_code_depnum_ccdc_archive 'CCDC 1493175'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N O3 S'
_chemical_formula_sum            'C17 H19 N O3 S'
_chemical_formula_weight         317.39

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                   7.965(9)
_cell_length_b                   8.677(10)
_cell_length_c                   12.496(14)
_cell_angle_alpha                89.035(18)
_cell_angle_beta                 83.993(18)
_cell_angle_gamma                68.355(17)
_cell_volume                     798.1(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4439
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.06

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793027
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12558
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         28.642
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3921
_reflns_number_gt                3066
_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 SAINT'
_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)+(0.0739P)²+0.1318P] 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         3921
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1357
_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 0.28459(6) 0.08776(6) 0.20835(4) 0.05847(17) Uani 1 1 d . . . . .
O1 O 0.12694(19) 0.07850(19) 0.27115(12) 0.0714(4) Uani 1 1 d . . . . .
O2 O 0.3772(2) -0.03196(19) 0.12421(12) 0.0812(4) Uani 1 1 d . . . . .
O3 O 0.2315(2) 0.3336(3) 0.59562(15) 0.1128(7) Uani 1 1 d . . . . .
N1 N 0.43223(19) 0.07339(19) 0.29252(12) 0.0581(4) Uani 1 1 d . . . . .
C1 C 0.3721(2) 0.1672(2) 0.39621(13) 0.0531(4) Uani 1 1 d . . . . .
H1B H 0.3321 0.1042 0.4511 0.064 Uiso 1 1 calc R U . . .
H1C H 0.2742 0.2726 0.3886 0.064 Uiso 1 1 calc R U . . .
C2 C 0.5414(2) 0.1921(2) 0.42323(15) 0.0546(4) Uani 1 1 d . . . . .
C3 C 0.6721(3) 0.1347(3) 0.34144(18) 0.0701(5) Uani 1 1 d . . . . .
H3A H 0.7873 0.1381 0.3420 0.084 Uiso 1 1 calc R U . . .
C4 C 0.6167(3) 0.0655(3) 0.25007(18) 0.0722(6) Uani 1 1 d . . . . .
H4A H 0.6981 -0.0478 0.2328 0.087 Uiso 1 1 calc R U . . .
H4B H 0.6128 0.1321 0.1866 0.087 Uiso 1 1 calc R U . . .
C5 C 0.5449(2) 0.2674(2) 0.52695(16) 0.0576(4) Uani 1 1 d . . . . .
C6 C 0.3821(3) 0.3303(3) 0.60629(18) 0.0722(5) Uani 1 1 d . . . . .
C7 C 0.4332(3) 0.3923(3) 0.7057(2) 0.0830(6) Uani 1 1 d . . . . .
H7A H 0.3600 0.5085 0.7202 0.100 Uiso 1 1 calc R U . . .
H7B H 0.4167 0.3291 0.7679 0.100 Uiso 1 1 calc R U . . .
C8 C 0.6312(3) 0.3673(3) 0.6792(2) 0.0827(7) Uani 1 1 d . . . . .
H8A H 0.6475 0.4727 0.6805 0.099 Uiso 1 1 calc R U . . .
H8B H 0.7042 0.2951 0.7308 0.099 Uiso 1 1 calc R U . . .
C9 C 0.6849(3) 0.2896(3) 0.56860(19) 0.0700(5) Uani 1 1 d . . . . .
C10 C 0.8753(3) 0.2473(4) 0.5190(3) 0.1136(10) Uani 1 1 d . . . . .
H10A H 0.9235 0.1342 0.4933 0.170 Uiso 1 1 calc R U . . .
H10B H 0.9480 0.2616 0.5718 0.170 Uiso 1 1 calc R U . . .
H10C H 0.8771 0.3191 0.4599 0.170 Uiso 1 1 calc R U . . .
C11 C 0.2248(2) 0.2867(2) 0.15137(13) 0.0530(4) Uani 1 1 d . . . . .
C12 C 0.0847(2) 0.4197(2) 0.20296(14) 0.0583(4) Uani 1 1 d . . . . .
H12A H 0.0187 0.4039 0.2652 0.070 Uiso 1 1 calc R U . . .
C13 C 0.0438(3) 0.5762(3) 0.16112(17) 0.0675(5) Uani 1 1 d . . . . .
H13A H -0.0505 0.6650 0.1961 0.081 Uiso 1 1 calc R U . . .
C14 C 0.1398(3) 0.6051(3) 0.06785(17) 0.0681(5) Uani 1 1 d . . . . .
C15 C 0.2785(3) 0.4701(3) 0.01732(16) 0.0726(6) Uani 1 1 d . . . . .
H15A H 0.3442 0.4861 -0.0450 0.087 Uiso 1 1 calc R U . . .
C16 C 0.3219(3) 0.3114(3) 0.05739(15) 0.0649(5) Uani 1 1 d . . . . .
H16A H 0.4150 0.2223 0.0218 0.078 Uiso 1 1 calc R U . . .
C17 C 0.0957(4) 0.7767(3) 0.0237(2) 0.1012(9) Uani 1 1 d . . . . .
H17A H -0.0316 0.8399 0.0403 0.152 Uiso 1 1 calc R U . . .
H17B H 0.1259 0.7689 -0.0529 0.152 Uiso 1 1 calc R U . . .
H17C H 0.1647 0.8305 0.0557 0.152 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 1.4274(18) . ?
S1 O1 1.4371(19) . ?
S1 N1 1.628(2) . ?
S1 C11 1.771(3) . ?
O3 C6 1.211(3) . ?
N1 C1 1.479(3) . ?
N1 C4 1.486(3) . ?
C1 C2 1.514(3) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.337(3) . ?
C2 C5 1.469(3) . ?
C3 C4 1.478(3) . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.355(3) . ?
C5 C6 1.479(3) . ?
C6 C7 1.512(3) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.498(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.490(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.385(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.381(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.397(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.384(3) . ?
C14 C17 1.507(4) . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 O1 119.88(10) . . ?
O2 S1 N1 106.45(11) . . ?
O1 S1 N1 106.46(12) . . ?
O2 S1 C11 107.60(12) . . ?
O1 S1 C11 108.48(9) . . ?
N1 S1 C11 107.38(9) . . ?
C1 N1 C4 110.68(15) . . ?
C1 N1 S1 119.66(13) . . ?
C4 N1 S1 119.12(15) . . ?
N1 C1 C2 103.17(14) . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
N1 C1 H1C 111.1 . . ?
C2 C1 H1C 111.1 . . ?
H1B C1 H1C 109.1 . . ?
C3 C2 C5 129.87(18) . . ?
C3 C2 C1 109.39(19) . . ?
C5 C2 C1 120.74(15) . . ?
C2 C3 C4 113.89(19) . . ?
C2 C3 H3A 123.1 . . ?
C4 C3 H3A 123.1 . . ?
C3 C4 N1 102.08(16) . . ?
C3 C4 H4A 111.4 . . ?
N1 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
N1 C4 H4B 111.4 . . ?
H4A C4 H4B 109.2 . . ?
C9 C5 C2 129.49(19) . . ?
C9 C5 C6 108.6(2) . . ?
C2 C5 C6 121.90(17) . . ?
O3 C6 C5 126.9(2) . . ?
O3 C6 C7 124.4(2) . . ?
C5 C6 C7 108.7(2) . . ?
C8 C7 C6 104.7(2) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 105.80(17) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C5 C9 C10 128.6(2) . . ?
C5 C9 C8 112.2(2) . . ?
C10 C9 C8 119.1(2) . . ?
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 . . ?
C12 C11 C16 119.87(19) . . ?
C12 C11 S1 119.50(15) . . ?
C16 C11 S1 120.59(15) . . ?
C13 C12 C11 119.42(19) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 122.03(19) . . ?
C12 C13 H13A 119.0 . . ?
C14 C13 H13A 119.0 . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C17 120.9(2) . . ?
C13 C14 C17 121.6(2) . . ?
C14 C15 C16 121.7(2) . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C15 C16 C11 119.51(19) . . ?
C15 C16 H16A 120.2 . . ?
C11 C16 H16A 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 N1 C1 -172.36(13) . . . . ?
O1 S1 N1 C1 -43.40(16) . . . . ?
C11 S1 N1 C1 72.63(15) . . . . ?
O2 S1 N1 C4 46.17(17) . . . . ?
O1 S1 N1 C4 175.13(14) . . . . ?
C11 S1 N1 C4 -68.84(16) . . . . ?
C4 N1 C1 C2 -8.71(19) . . . . ?
S1 N1 C1 C2 -153.15(13) . . . . ?
N1 C1 C2 C3 5.2(2) . . . . ?
N1 C1 C2 C5 -174.02(15) . . . . ?
C5 C2 C3 C4 179.31(18) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 N1 -5.4(2) . . . . ?
C1 N1 C4 C3 8.7(2) . . . . ?
S1 N1 C4 C3 153.36(15) . . . . ?
C3 C2 C5 C9 -4.0(3) . . . . ?
C1 C2 C5 C9 175.03(18) . . . . ?
C3 C2 C5 C6 177.4(2) . . . . ?
C1 C2 C5 C6 -3.5(3) . . . . ?
C9 C5 C6 O3 178.4(3) . . . . ?
C2 C5 C6 O3 -2.7(4) . . . . ?
C9 C5 C6 C7 -1.4(2) . . . . ?
C2 C5 C6 C7 177.45(18) . . . . ?
O3 C6 C7 C8 -178.2(2) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C2 C5 C9 C10 1.8(4) . . . . ?
C6 C5 C9 C10 -179.5(2) . . . . ?
C2 C5 C9 C8 -178.19(18) . . . . ?
C6 C5 C9 C8 0.5(2) . . . . ?
C7 C8 C9 C5 0.5(2) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
O2 S1 C11 C12 158.24(14) . . . . ?
O1 S1 C11 C12 27.17(16) . . . . ?
N1 S1 C11 C12 -87.52(17) . . . . ?
O2 S1 C11 C16 -24.14(17) . . . . ?
O1 S1 C11 C16 -155.21(14) . . . . ?
N1 S1 C11 C16 90.10(17) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
S1 C11 C12 C13 177.00(13) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C17 -179.16(18) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C17 C14 C15 C16 179.45(18) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
S1 C11 C16 C15 -176.70(14) . . . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_ot498
_database_code_depnum_ccdc_archive 'CCDC 1493176'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-08-15 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         'C24 H27 N O5 S2'
_chemical_formula_sum            'C24 H27 N O5 S2'
_chemical_formula_weight         473.58

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.607(4)
_cell_length_b                   7.076(3)
_cell_length_c                   15.851(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.393(10)
_cell_angle_gamma                90
_cell_volume                     1189.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1555
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.099975
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7368
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.285
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             4812
_reflns_number_gt                2992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_max     0.753
_reflns_Friedel_fraction_full    0.820

_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 SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0811P)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 815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4812
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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 0.05311(18) 0.5073(3) 0.24257(12) 0.0631(6) Uani 1 1 d . . . . .
S9 S 0.41052(18) 0.2792(3) -0.22566(11) 0.0611(5) Uani 1 1 d . . . . .
O1 O 0.0413(6) 0.6806(8) 0.2870(3) 0.0809(17) Uani 1 1 d . . . . .
O2 O -0.0568(5) 0.3989(9) 0.2238(4) 0.0831(18) Uani 1 1 d . . . . .
O3 O 0.4975(5) 0.3897(9) -0.1778(3) 0.0780(17) Uani 1 1 d . . . . .
O4 O 0.4558(6) 0.1206(9) -0.2726(4) 0.0839(18) Uani 1 1 d . . . . .
O15 O 0.4063(5) 0.0467(9) -0.0431(3) 0.0789(16) Uani 1 1 d . . . . .
N1 N 0.1130(6) 0.5583(9) 0.1541(4) 0.0653(17) Uani 1 1 d . . . . .
C1 C 0.1577(7) 0.3615(11) 0.3007(4) 0.0522(18) Uani 1 1 d . . . . .
C2 C 0.1404(9) 0.1704(12) 0.3027(5) 0.066(2) Uani 1 1 d . . . . .
H2 H 0.0734 0.1160 0.2726 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2210(9) 0.0594(12) 0.3487(5) 0.073(2) Uani 1 1 d . . . . .
H3 H 0.2064 -0.0701 0.3507 0.087 Uiso 1 1 calc R U . . .
C4 C 0.3236(8) 0.1326(15) 0.3924(5) 0.071(2) Uani 1 1 d . . . . .
C5 C 0.3417(9) 0.3237(16) 0.3875(6) 0.095(3) Uani 1 1 d . . . . .
H5 H 0.4107 0.3776 0.4157 0.113 Uiso 1 1 calc R U . . .
C6 C 0.2604(9) 0.4380(14) 0.3420(6) 0.086(3) Uani 1 1 d . . . . .
H6 H 0.2752 0.5674 0.3391 0.103 Uiso 1 1 calc R U . . .
C7 C 0.4115(9) 0.011(2) 0.4450(6) 0.108(3) Uani 1 1 d . . . . .
H7A H 0.3934 0.0275 0.5036 0.130 Uiso 1 1 calc R U . . .
H7B H 0.4970 0.0483 0.4354 0.130 Uiso 1 1 calc R U . . .
H7C H 0.4001 -0.1187 0.4295 0.130 Uiso 1 1 calc R U . . .
C8 C 0.1379(8) 0.4020(12) 0.0944(5) 0.070(2) Uani 1 1 d . . . . .
H8A H 0.1565 0.2852 0.1242 0.084 Uiso 1 1 calc R U . . .
H8B H 0.0665 0.3819 0.0560 0.084 Uiso 1 1 calc R U . . .
C9 C 0.2490(7) 0.4704(11) 0.0489(4) 0.0563(18) Uani 1 1 d . . . . .
C10 C 0.2855(7) 0.6386(12) 0.0786(5) 0.064(2) Uani 1 1 d . . . . .
H10 H 0.3540 0.7049 0.0581 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2086(8) 0.7075(12) 0.1456(5) 0.076(3) Uani 1 1 d . . . . .
H11I H 0.1697 0.8273 0.1305 0.091 Uiso 1 1 calc R U . . .
H11J H 0.2578 0.7229 0.1975 0.091 Uiso 1 1 calc R U . . .
C12 C 0.3120(7) 0.3558(11) -0.0172(4) 0.0587(19) Uani 1 1 d . . . . .
H12 H 0.3919 0.4183 -0.0296 0.070 Uiso 1 1 calc R U . . .
C13 C 0.3434(9) 0.1603(12) 0.0170(5) 0.076(2) Uani 1 1 d . . . . .
H13E H 0.3966 0.1728 0.0673 0.092 Uiso 1 1 calc R U . . .
H13F H 0.2661 0.0978 0.0328 0.092 Uiso 1 1 calc R U . . .
C14 C 0.3283(8) 0.0112(13) -0.1137(5) 0.075(2) Uani 1 1 d . . . . .
H14I H 0.2547 -0.0581 -0.0959 0.089 Uiso 1 1 calc R U . . .
H14J H 0.3733 -0.0681 -0.1527 0.089 Uiso 1 1 calc R U . . .
C15 C 0.2857(7) 0.1884(11) -0.1588(4) 0.061(2) Uani 1 1 d . . . . .
H15 H 0.2149 0.1529 -0.1964 0.073 Uiso 1 1 calc R U . . .
C16 C 0.2376(6) 0.3383(10) -0.0995(4) 0.0532(18) Uani 1 1 d . . . . .
C17 C 0.1427(7) 0.4442(12) -0.1207(5) 0.071(2) Uani 1 1 d . . . . .
H17E H 0.1161 0.5385 -0.0844 0.086 Uiso 1 1 calc R U . . .
H17F H 0.1010 0.4260 -0.1724 0.086 Uiso 1 1 calc R U . . .
C18 C 0.3279(7) 0.4290(11) -0.2952(4) 0.0504(17) Uani 1 1 d . . . . .
C19 C 0.2427(9) 0.3548(14) -0.3529(5) 0.081(3) Uani 1 1 d . . . . .
H19 H 0.2301 0.2249 -0.3559 0.097 Uiso 1 1 calc R U . . .
C20 C 0.1776(9) 0.4709(17) -0.4051(6) 0.092(3) Uani 1 1 d . . . . .
H20 H 0.1209 0.4188 -0.4442 0.110 Uiso 1 1 calc R U . . .
C21 C 0.1919(8) 0.6643(16) -0.4025(5) 0.075(3) Uani 1 1 d . . . . .
C22 C 0.2792(9) 0.7353(13) -0.3456(5) 0.071(2) Uani 1 1 d . . . . .
H22 H 0.2934 0.8649 -0.3442 0.086 Uiso 1 1 calc R U . . .
C23 C 0.3457(7) 0.6226(12) -0.2911(5) 0.063(2) Uani 1 1 d . . . . .
H23 H 0.4022 0.6748 -0.2518 0.076 Uiso 1 1 calc R U . . .
C24 C 0.1145(9) 0.7937(18) -0.4589(6) 0.110(4) Uani 1 1 d . . . . .
H23C H 0.0868 0.7259 -0.5084 0.132 Uiso 1 1 calc R U . . .
H24C H 0.1650 0.8996 -0.4751 0.132 Uiso 1 1 calc R U . . .
H24D H 0.0425 0.8378 -0.4291 0.132 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 1.421(6) . ?
S1 O1 1.421(6) . ?
S1 N1 1.594(6) . ?
S1 C1 1.759(8) . ?
S9 O3 1.416(6) . ?
S9 O4 1.436(6) . ?
S9 C18 1.749(7) . ?
S9 C15 1.832(7) . ?
O15 C14 1.398(9) . ?
O15 C13 1.424(9) . ?
N1 C11 1.472(10) . ?
N1 C8 1.484(10) . ?
C1 C2 1.365(10) . ?
C1 C6 1.368(11) . ?
C2 C3 1.360(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(14) . ?
C4 C7 1.502(12) . ?
C5 C6 1.374(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.478(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.335(11) . ?
C9 C12 1.495(10) . ?
C10 C11 1.439(10) . ?
C10 H10 0.9300 . ?
C11 H11I 0.9700 . ?
C11 H11J 0.9700 . ?
C12 C16 1.513(10) . ?
C12 C13 1.520(11) . ?
C12 H12 0.9800 . ?
C13 H13E 0.9700 . ?
C13 H13F 0.9700 . ?
C14 C15 1.507(11) . ?
C14 H14I 0.9700 . ?
C14 H14J 0.9700 . ?
C15 C16 1.515(10) . ?
C15 H15 0.9800 . ?
C16 C17 1.293(10) . ?
C17 H17E 0.9300 . ?
C17 H17F 0.9300 . ?
C18 C19 1.374(10) . ?
C18 C23 1.385(10) . ?
C19 C20 1.344(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(14) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(12) . ?
C21 C24 1.509(12) . ?
C22 C23 1.360(11) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H23C 0.9600 . ?
C24 H24C 0.9600 . ?
C24 H24D 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 O1 119.2(4) . . ?
O2 S1 N1 106.3(3) . . ?
O1 S1 N1 106.4(3) . . ?
O2 S1 C1 107.3(4) . . ?
O1 S1 C1 107.9(4) . . ?
N1 S1 C1 109.5(3) . . ?
O3 S9 O4 119.2(4) . . ?
O3 S9 C18 108.2(4) . . ?
O4 S9 C18 108.4(3) . . ?
O3 S9 C15 110.8(3) . . ?
O4 S9 C15 106.3(4) . . ?
C18 S9 C15 102.7(3) . . ?
C14 O15 C13 111.0(6) . . ?
C11 N1 C8 110.0(6) . . ?
C11 N1 S1 122.2(5) . . ?
C8 N1 S1 118.3(5) . . ?
C2 C1 C6 119.1(8) . . ?
C2 C1 S1 120.6(6) . . ?
C6 C1 S1 120.2(7) . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 122.1(8) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 116.9(9) . . ?
C5 C4 C7 120.6(10) . . ?
C3 C4 C7 122.4(10) . . ?
C4 C5 C6 121.6(9) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 120.0(9) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 102.9(6) . . ?
C9 C8 H8A 111.2 . . ?
N1 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
N1 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 110.4(7) . . ?
C10 C9 C12 126.9(7) . . ?
C8 C9 C12 122.7(7) . . ?
C9 C10 C11 113.4(7) . . ?
C9 C10 H10 123.3 . . ?
C11 C10 H10 123.3 . . ?
C10 C11 N1 103.3(6) . . ?
C10 C11 H11I 111.1 . . ?
N1 C11 H11I 111.1 . . ?
C10 C11 H11J 111.1 . . ?
N1 C11 H11J 111.1 . . ?
H11I C11 H11J 109.1 . . ?
C9 C12 C16 114.6(6) . . ?
C9 C12 C13 110.0(6) . . ?
C16 C12 C13 109.8(6) . . ?
C9 C12 H12 107.4 . . ?
C16 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
O15 C13 C12 112.2(6) . . ?
O15 C13 H13E 109.2 . . ?
C12 C13 H13E 109.2 . . ?
O15 C13 H13F 109.2 . . ?
C12 C13 H13F 109.2 . . ?
H13E C13 H13F 107.9 . . ?
O15 C14 C15 113.3(7) . . ?
O15 C14 H14I 108.9 . . ?
C15 C14 H14I 108.9 . . ?
O15 C14 H14J 108.9 . . ?
C15 C14 H14J 108.9 . . ?
H14I C14 H14J 107.7 . . ?
C14 C15 C16 112.9(6) . . ?
C14 C15 S9 110.7(5) . . ?
C16 C15 S9 111.9(5) . . ?
C14 C15 H15 107.0 . . ?
C16 C15 H15 107.0 . . ?
S9 C15 H15 107.0 . . ?
C17 C16 C12 124.3(7) . . ?
C17 C16 C15 121.0(7) . . ?
C12 C16 C15 114.6(6) . . ?
C16 C17 H17E 120.0 . . ?
C16 C17 H17F 120.0 . . ?
H17E C17 H17F 120.0 . . ?
C19 C18 C23 119.8(8) . . ?
C19 C18 S9 120.0(7) . . ?
C23 C18 S9 120.3(6) . . ?
C20 C19 C18 119.7(9) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 122.3(9) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C22 C21 C20 117.1(8) . . ?
C22 C21 C24 121.1(10) . . ?
C20 C21 C24 121.8(10) . . ?
C23 C22 C21 122.3(9) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C18 118.8(8) . . ?
C22 C23 H23 120.6 . . ?
C18 C23 H23 120.6 . . ?
C21 C24 H23C 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H23C C24 H24C 109.5 . . ?
C21 C24 H24D 109.5 . . ?
H23C C24 H24D 109.5 . . ?
H24C C24 H24D 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 N1 C11 164.3(6) . . . . ?
O1 S1 N1 C11 36.3(7) . . . . ?
C1 S1 N1 C11 -80.2(7) . . . . ?
O2 S1 N1 C8 -52.8(7) . . . . ?
O1 S1 N1 C8 179.2(6) . . . . ?
C1 S1 N1 C8 62.7(7) . . . . ?
O2 S1 C1 C2 15.6(8) . . . . ?
O1 S1 C1 C2 145.3(6) . . . . ?
N1 S1 C1 C2 -99.3(7) . . . . ?
O2 S1 C1 C6 -166.9(7) . . . . ?
O1 S1 C1 C6 -37.3(7) . . . . ?
N1 S1 C1 C6 78.2(7) . . . . ?
C6 C1 C2 C3 3.3(13) . . . . ?
S1 C1 C2 C3 -179.2(6) . . . . ?
C1 C2 C3 C4 -1.9(13) . . . . ?
C2 C3 C4 C5 -0.2(13) . . . . ?
C2 C3 C4 C7 178.6(8) . . . . ?
C3 C4 C5 C6 0.8(15) . . . . ?
C7 C4 C5 C6 -178.0(9) . . . . ?
C2 C1 C6 C5 -2.7(13) . . . . ?
S1 C1 C6 C5 179.8(7) . . . . ?
C4 C5 C6 C1 0.6(16) . . . . ?
C11 N1 C8 C9 -2.0(9) . . . . ?
S1 N1 C8 C9 -149.1(5) . . . . ?
N1 C8 C9 C10 1.3(9) . . . . ?
N1 C8 C9 C12 178.1(6) . . . . ?
C8 C9 C10 C11 -0.1(10) . . . . ?
C12 C9 C10 C11 -176.7(7) . . . . ?
C9 C10 C11 N1 -1.1(9) . . . . ?
C8 N1 C11 C10 1.9(9) . . . . ?
S1 N1 C11 C10 147.5(6) . . . . ?
C10 C9 C12 C16 -111.7(9) . . . . ?
C8 C9 C12 C16 72.0(9) . . . . ?
C10 C9 C12 C13 124.1(8) . . . . ?
C8 C9 C12 C13 -52.1(9) . . . . ?
C14 O15 C13 C12 -64.1(9) . . . . ?
C9 C12 C13 O15 -178.7(7) . . . . ?
C16 C12 C13 O15 54.4(9) . . . . ?
C13 O15 C14 C15 59.6(9) . . . . ?
O15 C14 C15 C16 -47.2(9) . . . . ?
O15 C14 C15 S9 79.1(7) . . . . ?
O3 S9 C15 C14 -83.1(6) . . . . ?
O4 S9 C15 C14 47.7(6) . . . . ?
C18 S9 C15 C14 161.5(5) . . . . ?
O3 S9 C15 C16 43.8(6) . . . . ?
O4 S9 C15 C16 174.6(5) . . . . ?
C18 S9 C15 C16 -71.6(5) . . . . ?
C9 C12 C16 C17 15.3(11) . . . . ?
C13 C12 C16 C17 139.6(8) . . . . ?
C9 C12 C16 C15 -166.8(6) . . . . ?
C13 C12 C16 C15 -42.5(9) . . . . ?
C14 C15 C16 C17 -142.6(8) . . . . ?
S9 C15 C16 C17 91.7(8) . . . . ?
C14 C15 C16 C12 39.4(9) . . . . ?
S9 C15 C16 C12 -86.3(7) . . . . ?
O3 S9 C18 C19 175.9(7) . . . . ?
O4 S9 C18 C19 45.3(8) . . . . ?
C15 S9 C18 C19 -66.9(7) . . . . ?
O3 S9 C18 C23 -5.6(7) . . . . ?
O4 S9 C18 C23 -136.2(6) . . . . ?
C15 S9 C18 C23 111.5(7) . . . . ?
C23 C18 C19 C20 0.2(14) . . . . ?
S9 C18 C19 C20 178.7(7) . . . . ?
C18 C19 C20 C21 -0.7(16) . . . . ?
C19 C20 C21 C22 2.0(15) . . . . ?
C19 C20 C21 C24 -177.5(9) . . . . ?
C20 C21 C22 C23 -2.8(13) . . . . ?
C24 C21 C22 C23 176.7(8) . . . . ?
C21 C22 C23 C18 2.3(12) . . . . ?
C19 C18 C23 C22 -1.0(12) . . . . ?
S9 C18 C23 C22 -179.4(6) . . . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.066

