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

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

data_cd21482
_database_code_depnum_ccdc_archive 'CCDC 992536'
_audit_update_record             
;
2014-03-19 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 O3 S3'
_chemical_formula_weight         376.49

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'
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                   4.5264(7)
_cell_length_b                   13.238(2)
_cell_length_c                   14.614(2)
_cell_angle_alpha                85.804(4)
_cell_angle_beta                 82.143(3)
_cell_angle_gamma                84.097(4)
_cell_volume                     861.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1441
_cell_measurement_theta_min      6.199
_cell_measurement_theta_max      51.731

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.444
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6187
_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            5281
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3392
_reflns_number_gt                2706
_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)+(0.0789P)²+0.1852P] 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         3392
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.7053(2) 0.43668(6) 0.39209(6) 0.0518(2) Uani 1 1 d . . . . .
S2 S 0.13975(18) 0.12199(6) 0.46361(5) 0.0446(2) Uani 1 1 d . . . . .
S3 S 0.26382(19) 0.31736(6) 0.52862(5) 0.0474(2) Uani 1 1 d . . . . .
O1 O 0.4536(5) 0.20167(14) 0.27836(12) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.0639(6) -0.07940(17) 0.26908(14) 0.0610(6) Uani 1 1 d . . . . .
O3 O 0.0532(5) -0.02484(14) 0.12037(13) 0.0447(5) Uani 1 1 d . . . . .
C1 C 0.9463(7) 0.4885(2) 0.3060(2) 0.0490(7) Uani 1 1 d . . . . .
H1 H 1.0392 0.5468 0.3116 0.059 Uiso 1 1 calc R U . . .
C2 C 0.9880(7) 0.4368(2) 0.2296(2) 0.0510(7) Uani 1 1 d . . . . .
H2 H 1.1151 0.4557 0.1771 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8208(6) 0.3495(2) 0.23496(19) 0.0393(6) Uani 1 1 d . . . . .
H3 H 0.8210 0.3062 0.1876 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6551(6) 0.34006(19) 0.32472(18) 0.0355(6) Uani 1 1 d . . . . .
C5 C 0.4669(6) 0.25745(19) 0.35481(17) 0.0341(6) Uani 1 1 d . . . . .
C6 C 0.3169(6) 0.2348(2) 0.43868(18) 0.0375(6) Uani 1 1 d . . . . .
C7 C 0.3667(7) 0.0496(2) 0.37587(17) 0.0403(6) Uani 1 1 d . . . . .
H7A H 0.5731 0.0397 0.3884 0.048 Uiso 1 1 calc R U . . .
H7B H 0.2938 -0.0166 0.3744 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3460(6) 0.1085(2) 0.28614(18) 0.0357(6) Uani 1 1 d . . . . .
C9 C 0.2410(6) 0.0806(2) 0.21191(18) 0.0395(6) Uani 1 1 d . . . . .
H9 H 0.2479 0.1256 0.1599 0.047 Uiso 1 1 calc R U . . .
C10 C 0.1154(6) -0.0159(2) 0.20673(18) 0.0397(6) Uani 1 1 d . . . . .
C11 C -0.0803(7) -0.1166(2) 0.1047(2) 0.0479(7) Uani 1 1 d . . . . .
H11A H -0.1977 -0.1027 0.0537 0.057 Uiso 1 1 calc R U . . .
H11B H -0.2145 -0.1355 0.1595 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1514(6) -0.2032(2) 0.08324(19) 0.0403(6) Uani 1 1 d . . . . .
C13 C 0.2297(7) -0.2751(2) 0.1528(2) 0.0501(7) Uani 1 1 d . . . . .
H13 H 0.1362 -0.2693 0.2132 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4467(8) -0.3550(3) 0.1321(3) 0.0592(9) Uani 1 1 d . . . . .
H14 H 0.4993 -0.4024 0.1787 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5835(8) -0.3641(3) 0.0428(3) 0.0645(9) Uani 1 1 d . . . . .
H15 H 0.7279 -0.4179 0.0290 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5070(9) -0.2930(3) -0.0270(2) 0.0637(9) Uani 1 1 d . . . . .
H16 H 0.5998 -0.2992 -0.0874 0.076 Uiso 1 1 calc R U . . .
C17 C 0.2928(7) -0.2134(2) -0.0062(2) 0.0523(8) Uani 1 1 d . . . . .
H17 H 0.2426 -0.1657 -0.0529 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4499(8) 0.2458(3) 0.6173(2) 0.0546(8) Uani 1 1 d . . . . .
H18A H 0.3604 0.1831 0.6333 0.082 Uiso 1 1 calc R U . . .
H18B H 0.4302 0.2848 0.6710 0.082 Uiso 1 1 calc R U . . .
H18C H 0.6583 0.2313 0.5948 0.082 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 C1 1.702(3) . ?
S1 C4 1.721(3) . ?
S2 C6 1.759(3) . ?
S2 C7 1.799(3) . ?
S3 C6 1.746(3) . ?
S3 C18 1.800(3) . ?
O1 C8 1.363(3) . ?
O1 C5 1.395(3) . ?
O2 C10 1.209(3) . ?
O3 C10 1.346(3) . ?
O3 C11 1.457(3) . ?
C1 C2 1.333(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.437(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.423(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.461(4) . ?
C5 C6 1.347(4) . ?
C7 C8 1.485(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.332(4) . ?
C9 C10 1.462(4) . ?
C9 H9 0.9300 . ?
C11 C12 1.493(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.384(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 S1 C4 91.67(14) . . ?
C6 S2 C7 96.69(13) . . ?
C6 S3 C18 102.95(14) . . ?
C8 O1 C5 122.6(2) . . ?
C10 O3 C11 116.4(2) . . ?
C2 C1 S1 113.0(2) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 C3 114.7(3) . . ?
C1 C2 H2 122.6 . . ?
C3 C2 H2 122.6 . . ?
C4 C3 C2 108.7(3) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
C3 C4 C5 123.3(2) . . ?
C3 C4 S1 111.9(2) . . ?
C5 C4 S1 124.8(2) . . ?
C6 C5 O1 122.2(2) . . ?
C6 C5 C4 129.7(2) . . ?
O1 C5 C4 108.0(2) . . ?
C5 C6 S3 123.1(2) . . ?
C5 C6 S2 122.1(2) . . ?
S3 C6 S2 114.72(16) . . ?
C8 C7 S2 106.96(18) . . ?
C8 C7 H7A 110.3 . . ?
S2 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
S2 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C9 C8 O1 116.2(2) . . ?
C9 C8 C7 127.9(2) . . ?
O1 C8 C7 115.8(2) . . ?
C8 C9 C10 124.4(2) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
O2 C10 O3 122.9(2) . . ?
O2 C10 C9 127.2(2) . . ?
O3 C10 C9 109.9(2) . . ?
O3 C11 C12 111.9(2) . . ?
O3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C17 C12 C13 118.9(3) . . ?
C17 C12 C11 120.3(3) . . ?
C13 C12 C11 120.8(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
S3 C18 H18A 109.5 . . ?
S3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C4 S1 C1 C2 0.3(2) . . . . ?
S1 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 -178.1(2) . . . . ?
C2 C3 C4 S1 1.7(3) . . . . ?
C1 S1 C4 C3 -1.2(2) . . . . ?
C1 S1 C4 C5 178.6(2) . . . . ?
C8 O1 C5 C6 -14.9(4) . . . . ?
C8 O1 C5 C4 166.8(2) . . . . ?
C3 C4 C5 C6 174.5(3) . . . . ?
S1 C4 C5 C6 -5.3(4) . . . . ?
C3 C4 C5 O1 -7.4(3) . . . . ?
S1 C4 C5 O1 172.88(17) . . . . ?
O1 C5 C6 S3 -165.99(18) . . . . ?
C4 C5 C6 S3 11.9(4) . . . . ?
O1 C5 C6 S2 10.2(4) . . . . ?
C4 C5 C6 S2 -171.9(2) . . . . ?
C18 S3 C6 C5 -118.7(3) . . . . ?
C18 S3 C6 S2 64.87(19) . . . . ?
C7 S2 C6 C5 24.0(2) . . . . ?
C7 S2 C6 S3 -159.57(15) . . . . ?
C6 S2 C7 C8 -55.6(2) . . . . ?
C5 O1 C8 C9 155.7(2) . . . . ?
C5 O1 C8 C7 -25.6(3) . . . . ?
S2 C7 C8 C9 -119.0(3) . . . . ?
S2 C7 C8 O1 62.5(3) . . . . ?
O1 C8 C9 C10 -179.7(3) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C11 O3 C10 O2 -0.3(4) . . . . ?
C11 O3 C10 C9 -178.7(2) . . . . ?
C8 C9 C10 O2 7.0(5) . . . . ?
C8 C9 C10 O3 -174.8(3) . . . . ?
C10 O3 C11 C12 -85.3(3) . . . . ?
O3 C11 C12 C17 -84.0(3) . . . . ?
O3 C11 C12 C13 95.9(3) . . . . ?
C17 C12 C13 C14 0.2(4) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C11 C12 C17 C16 -179.9(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
C18 H18C S2 0.96 3.02 3.879(3) 149.3 1_655
C7 H7B O2 0.97 2.22 2.947(3) 130.4 .

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.060

_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_cd214587
_database_code_depnum_ccdc_archive 'CCDC 1029698'
_audit_update_record             
;
2014-10-17 deposited with the CCDC.
2015-03-05 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 H27 N O4 S'
_chemical_formula_weight         401.50

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.687(3)
_cell_length_b                   6.2286(5)
_cell_length_c                   23.0782(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.427(3)
_cell_angle_gamma                90
_cell_volume                     4368.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1840
_cell_measurement_theta_min      5.129
_cell_measurement_theta_max      55.486

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_T_max  0.7457
_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            12101
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4064
_reflns_number_gt                2630
_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)+(0.0766P)²+0.8909P] 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         4064
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.18701(3) 0.35873(14) 1.03803(4) 0.0702(3) Uani 1 1 d . . . . .
H1A H 0.1682 0.3500 1.0764 0.105 Uiso 1 1 calc R U . . .
N1 N 0.10575(10) 0.9658(5) 1.04752(13) 0.0643(8) Uani 1 1 d . . . . .
O1 O 0.10633(9) 0.6100(4) 1.05818(11) 0.0847(8) Uani 1 1 d . . . . .
O2 O 0.25953(10) 0.4833(6) 0.81233(13) 0.1090(10) Uani 1 1 d . . . . .
O3 O 0.09995(7) 0.2661(3) 0.94764(10) 0.0688(7) Uani 1 1 d . . . . .
O4 O 0.08657(6) 0.6047(3) 0.91470(9) 0.0510(5) Uani 1 1 d . . . . .
C1 C 0.11956(10) 0.7703(5) 1.03883(13) 0.0538(8) Uani 1 1 d . . . . .
C2 C 0.15246(9) 0.7626(5) 1.00225(12) 0.0490(7) Uani 1 1 d . . . . .
H2A H 0.1809 0.8088 1.0276 0.059 Uiso 1 1 calc R U . . .
H2B H 0.1433 0.8628 0.9688 0.059 Uiso 1 1 calc R U . . .
C3 C 0.15710(9) 0.5392(4) 0.97729(12) 0.0475(7) Uani 1 1 d . . . . .
C4 C 0.18343(9) 0.5389(5) 0.93146(13) 0.0497(7) Uani 1 1 d . . . . .
C5 C 0.18346(11) 0.3561(5) 0.89679(16) 0.0682(9) Uani 1 1 d . . . . .
H5 H 0.1659 0.2399 0.9002 0.082 Uiso 1 1 calc R U . . .
C6 C 0.20878(13) 0.3439(6) 0.85795(18) 0.0811(11) Uani 1 1 d . . . . .
H6 H 0.2085 0.2191 0.8357 0.097 Uiso 1 1 calc R U . . .
C7 C 0.23491(11) 0.5151(7) 0.85121(16) 0.0715(10) Uani 1 1 d . . . . .
C8 C 0.23501(10) 0.6962(6) 0.88426(15) 0.0640(9) Uani 1 1 d . . . . .
H8 H 0.2521 0.8130 0.8799 0.077 Uiso 1 1 calc R U . . .
C9 C 0.20983(10) 0.7077(5) 0.92424(14) 0.0565(8) Uani 1 1 d . . . . .
H9 H 0.2107 0.8320 0.9468 0.068 Uiso 1 1 calc R U . . .
C10 C 0.28941(15) 0.6452(9) 0.8077(2) 0.1152(17) Uani 1 1 d . . . . .
H10A H 0.2735 0.7710 0.7898 0.173 Uiso 1 1 calc R U . . .
H10B H 0.3071 0.5954 0.7828 0.173 Uiso 1 1 calc R U . . .
H10C H 0.3081 0.6795 0.8472 0.173 Uiso 1 1 calc R U . . .
C11 C 0.07320(11) 1.0062(6) 1.07940(15) 0.0744(10) Uani 1 1 d . . . . .
H11A H 0.0538 0.8829 1.0743 0.089 Uiso 1 1 calc R U . . .
H11B H 0.0555 1.1286 1.0609 0.089 Uiso 1 1 calc R U . . .
C12 C 0.09187(10) 1.0495(5) 1.14576(14) 0.0572(8) Uani 1 1 d . . . . .
C13 C 0.11010(14) 1.2446(6) 1.16581(19) 0.0834(11) Uani 1 1 d . . . . .
H13 H 0.1111 1.3507 1.1379 0.100 Uiso 1 1 calc R U . . .
C14 C 0.12699(16) 1.2867(8) 1.2264(2) 0.1023(14) Uani 1 1 d . . . . .
H14 H 0.1397 1.4195 1.2390 0.123 Uiso 1 1 calc R U . . .
C15 C 0.12519(15) 1.1370(9) 1.26742(19) 0.0964(14) Uani 1 1 d . . . . .
H15 H 0.1364 1.1658 1.3085 0.116 Uiso 1 1 calc R U . . .
C16 C 0.10688(14) 0.9433(9) 1.24862(19) 0.0942(13) Uani 1 1 d . . . . .
H16 H 0.1055 0.8392 1.2769 0.113 Uiso 1 1 calc R U . . .
C17 C 0.09022(12) 0.8991(6) 1.18770(17) 0.0748(10) Uani 1 1 d . . . . .
H17 H 0.0778 0.7655 1.1753 0.090 Uiso 1 1 calc R U . . .
C18 C 0.11121(10) 0.4486(5) 0.94589(13) 0.0490(7) Uani 1 1 d . . . . .
C19 C 0.03973(10) 0.5720(5) 0.88145(14) 0.0582(8) Uani 1 1 d . . . . .
C20 C 0.02606(12) 0.7947(6) 0.8574(2) 0.0900(13) Uani 1 1 d . . . . .
H20A H 0.0293 0.8923 0.8906 0.135 Uiso 1 1 calc R U . . .
H20B H -0.0041 0.7924 0.8334 0.135 Uiso 1 1 calc R U . . .
H20C H 0.0443 0.8410 0.8330 0.135 Uiso 1 1 calc R U . . .
C21 C 0.01519(12) 0.5004(7) 0.92559(18) 0.0882(12) Uani 1 1 d . . . . .
H21A H 0.0243 0.3578 0.9394 0.132 Uiso 1 1 calc R U . . .
H21B H -0.0159 0.5012 0.9059 0.132 Uiso 1 1 calc R U . . .
H21C H 0.0216 0.5967 0.9594 0.132 Uiso 1 1 calc R U . . .
C22 C 0.03631(13) 0.4160(7) 0.83155(16) 0.0880(12) Uani 1 1 d . . . . .
H22A H 0.0533 0.4666 0.8059 0.132 Uiso 1 1 calc R U . . .
H22B H 0.0061 0.4017 0.8084 0.132 Uiso 1 1 calc R U . . .
H22C H 0.0474 0.2790 0.8481 0.132 Uiso 1 1 calc R U . . .
H1 H 0.1151(9) 1.065(5) 1.0298(12) 0.045(8) 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 C3 1.837(3) . ?
S1 H1A 1.2000 . ?
N1 C1 1.328(4) . ?
N1 C11 1.448(4) . ?
N1 H1 0.84(3) . ?
O1 C1 1.216(3) . ?
O2 C7 1.360(4) . ?
O2 C10 1.408(5) . ?
O3 C18 1.195(3) . ?
O4 C18 1.325(3) . ?
O4 C19 1.479(3) . ?
C1 C2 1.516(4) . ?
C2 C3 1.529(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(4) . ?
C3 C18 1.537(4) . ?
C4 C9 1.383(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.364(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(5) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.502(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.359(4) . ?
C12 C13 1.369(5) . ?
C13 C14 1.374(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.356(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C22 1.487(5) . ?
C19 C20 1.511(5) . ?
C19 C21 1.513(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
C3 S1 H1A 109.5 . . ?
C1 N1 C11 123.3(3) . . ?
C1 N1 H1 115(2) . . ?
C11 N1 H1 121(2) . . ?
C7 O2 C10 118.0(4) . . ?
C18 O4 C19 122.1(2) . . ?
O1 C1 N1 122.3(3) . . ?
O1 C1 C2 122.8(3) . . ?
N1 C1 C2 114.9(3) . . ?
C1 C2 C3 113.2(2) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.2(2) . . ?
C4 C3 C18 107.7(2) . . ?
C2 C3 C18 109.4(2) . . ?
C4 C3 S1 105.27(19) . . ?
C2 C3 S1 110.69(19) . . ?
C18 C3 S1 110.49(19) . . ?
C9 C4 C5 117.0(3) . . ?
C9 C4 C3 123.5(3) . . ?
C5 C4 C3 119.4(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
O2 C7 C8 125.4(4) . . ?
O2 C7 C6 115.8(4) . . ?
C8 C7 C6 118.8(3) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 114.7(3) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C11 121.3(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.5(4) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O3 C18 O4 125.5(3) . . ?
O3 C18 C3 125.8(3) . . ?
O4 C18 C3 108.7(2) . . ?
O4 C19 C22 109.5(3) . . ?
O4 C19 C20 101.9(2) . . ?
C22 C19 C20 111.4(3) . . ?
O4 C19 C21 108.8(2) . . ?
C22 C19 C21 112.9(3) . . ?
C20 C19 C21 111.7(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 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
C11 N1 C1 O1 -1.4(5) . . . . ?
C11 N1 C1 C2 177.7(3) . . . . ?
O1 C1 C2 C3 16.3(4) . . . . ?
N1 C1 C2 C3 -162.8(3) . . . . ?
C1 C2 C3 C4 169.5(2) . . . . ?
C1 C2 C3 C18 49.4(3) . . . . ?
C1 C2 C3 S1 -72.6(3) . . . . ?
C2 C3 C4 C9 15.7(4) . . . . ?
C18 C3 C4 C9 136.8(3) . . . . ?
S1 C3 C4 C9 -105.3(3) . . . . ?
C2 C3 C4 C5 -168.1(3) . . . . ?
C18 C3 C4 C5 -47.0(3) . . . . ?
S1 C3 C4 C5 70.9(3) . . . . ?
C9 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 C6 -175.8(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C10 O2 C7 C8 3.5(5) . . . . ?
C10 O2 C7 C6 -174.7(4) . . . . ?
C5 C6 C7 O2 178.5(3) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
O2 C7 C8 C9 -177.5(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C4 -0.9(5) . . . . ?
C5 C4 C9 C8 0.2(4) . . . . ?
C3 C4 C9 C8 176.5(3) . . . . ?
C1 N1 C11 C12 92.8(4) . . . . ?
N1 C11 C12 C17 -105.0(4) . . . . ?
N1 C11 C12 C13 76.7(4) . . . . ?
C17 C12 C13 C14 1.1(6) . . . . ?
C11 C12 C13 C14 179.5(4) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
C11 C12 C17 C16 -178.8(3) . . . . ?
C15 C16 C17 C12 -0.1(6) . . . . ?
C19 O4 C18 O3 5.1(4) . . . . ?
C19 O4 C18 C3 -177.1(2) . . . . ?
C4 C3 C18 O3 95.4(3) . . . . ?
C2 C3 C18 O3 -141.2(3) . . . . ?
S1 C3 C18 O3 -19.1(4) . . . . ?
C4 C3 C18 O4 -82.4(3) . . . . ?
C2 C3 C18 O4 41.0(3) . . . . ?
S1 C3 C18 O4 163.11(19) . . . . ?
C18 O4 C19 C22 -65.3(3) . . . . ?
C18 O4 C19 C20 176.7(3) . . . . ?
C18 O4 C19 C21 58.6(4) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

