# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_b150117b_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1400890'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
_audit_creation_date             2015-01-22
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H32 N2 O2 S'
_chemical_formula_sum            'C28 H32 N2 O2 S'
_chemical_formula_weight         460.62
_chemical_melting_point          ?
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.3159(16)
_cell_length_b                   11.3266(14)
_cell_length_c                   12.5248(16)
_cell_angle_alpha                94.687(4)
_cell_angle_beta                 112.587(4)
_cell_angle_gamma                117.050(4)
_cell_volume                     1254.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9415
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            52007
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4554
_reflns_number_total             5110
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.510
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0932
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0801P)²+9.4694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2845
_refine_ls_wR_factor_ref         0.2879
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75398(13) 0.77364(13) 0.25333(11) 0.0220(4) Uani 1 1 d . . .
O2 O 0.7626(4) 1.0211(4) 0.3724(3) 0.0309(9) Uani 1 1 d . . .
O1 O 0.5973(5) 0.4641(4) 0.2058(4) 0.0361(10) Uani 1 1 d . . .
N2 N 0.8204(5) 0.6442(4) 0.4500(4) 0.0242(9) Uani 1 1 d . . .
H2 H 0.7810 0.6089 0.3727 0.029 Uiso 1 1 calc R . .
N1 N 0.5041(5) 0.8256(4) 0.1459(4) 0.0253(9) Uani 1 1 d . . .
H1 H 0.5969 0.8810 0.2000 0.030 Uiso 1 1 calc R . .
C9 C 0.7955(5) 0.8339(5) 0.4062(4) 0.0205(10) Uani 1 1 d . . .
C6 C 0.4561(5) 0.6895(5) 0.1211(4) 0.0195(9) Uani 1 1 d . . .
C10 C 0.8340(5) 0.7655(5) 0.4879(4) 0.0194(9) Uani 1 1 d . . .
C1 C 0.5578(5) 0.6479(5) 0.1724(4) 0.0201(9) Uani 1 1 d . . .
C14 C 0.7930(5) 0.9559(5) 0.4427(4) 0.0233(10) Uani 1 1 d . . .
C17 C 0.4251(5) 0.8917(5) 0.0963(4) 0.0229(10) Uani 1 1 d . . .
C11 C 0.8888(5) 0.8273(5) 0.6203(4) 0.0208(10) Uani 1 1 d . . .
H11A H 0.9965 0.8948 0.6594 0.025 Uiso 1 1 calc R . .
H11B H 0.8724 0.7540 0.6582 0.025 Uiso 1 1 calc R . .
C2 C 0.5095(6) 0.5041(5) 0.1592(4) 0.0236(10) Uani 1 1 d . . .
C12 C 0.8093(5) 0.8991(5) 0.6411(4) 0.0229(10) Uani 1 1 d . . .
C13 C 0.8292(6) 1.0076(5) 0.5733(5) 0.0248(10) Uani 1 1 d . . .
H13A H 0.7652 1.0423 0.5738 0.030 Uiso 1 1 calc R . .
H13B H 0.9328 1.0856 0.6178 0.030 Uiso 1 1 calc R . .
C23 C 0.8637(6) 0.5664(5) 0.5234(5) 0.0240(10) Uani 1 1 d . . .
C28 C 1.0108(6) 0.6241(6) 0.6136(5) 0.0290(11) Uani 1 1 d . . .
H28 H 1.0830 0.7173 0.6321 0.035 Uiso 1 1 calc R . .
C4 C 0.2400(6) 0.4501(5) 0.0810(5) 0.0266(11) Uani 1 1 d . . .
C3 C 0.3424(6) 0.3959(5) 0.0843(5) 0.0254(11) Uani 1 1 d . . .
H3A H 0.3185 0.3183 0.1170 0.030 Uiso 1 1 calc R . .
H3B H 0.3207 0.3605 0.0016 0.030 Uiso 1 1 calc R . .
C19 C 0.2505(7) 0.9196(6) -0.0669(5) 0.0358(13) Uani 1 1 d . . .
H19 H 0.1749 0.8854 -0.1470 0.043 Uiso 1 1 calc R . .
C24 C 0.7574(7) 0.4273(6) 0.4946(6) 0.0358(13) Uani 1 1 d . . .
H24 H 0.6595 0.3889 0.4327 0.043 Uiso 1 1 calc R . .
C5 C 0.2909(6) 0.5817(5) 0.0420(5) 0.0254(11) Uani 1 1 d . . .
H5A H 0.2708 0.5562 -0.0417 0.031 Uiso 1 1 calc R . .
H5B H 0.2324 0.6220 0.0455 0.031 Uiso 1 1 calc R . .
C16 C 0.8825(7) 0.9710(6) 0.7776(5) 0.0329(12) Uani 1 1 d . . .
H16A H 0.9878 1.0379 0.8078 0.049 Uiso 1 1 calc R . .
H16B H 0.8713 0.9026 0.8195 0.049 Uiso 1 1 calc R . .
H16C H 0.8345 1.0178 0.7911 0.049 Uiso 1 1 calc R . .
C15 C 0.6410(6) 0.7911(6) 0.5923(5) 0.0328(12) Uani 1 1 d . . .
H15A H 0.6301 0.7234 0.6350 0.049 Uiso 1 1 calc R . .
H15B H 0.5960 0.7453 0.5070 0.049 Uiso 1 1 calc R . .
H15C H 0.5919 0.8372 0.6045 0.049 Uiso 1 1 calc R . .
C20 C 0.2954(6) 1.0441(6) 0.0077(5) 0.0331(12) Uani 1 1 d . . .
H20 H 0.2506 1.0940 -0.0217 0.040 Uiso 1 1 calc R . .
C18 C 0.3168(7) 0.8447(6) -0.0238(5) 0.0337(13) Uani 1 1 d . . .
H18 H 0.2884 0.7624 -0.0760 0.040 Uiso 1 1 calc R . .
C22 C 0.4717(6) 1.0182(6) 0.1713(5) 0.0305(12) Uani 1 1 d . . .
H22 H 0.5460 1.0519 0.2519 0.037 Uiso 1 1 calc R . .
C26 C 0.9424(8) 0.4012(7) 0.6482(6) 0.0414(15) Uani 1 1 d . . .
H26 H 0.9689 0.3457 0.6900 0.050 Uiso 1 1 calc R . .
C27 C 1.0484(7) 0.5393(7) 0.6764(5) 0.0386(14) Uani 1 1 d . . .
H27 H 1.1463 0.5768 0.7379 0.046 Uiso 1 1 calc R . .
C8 C 0.0770(7) 0.3408(6) -0.0139(6) 0.0426(15) Uani 1 1 d . . .
H8A H 0.0431 0.2576 0.0094 0.064 Uiso 1 1 calc R . .
H8B H 0.0719 0.3193 -0.0919 0.064 Uiso 1 1 calc R . .
H8C H 0.0137 0.3769 -0.0187 0.064 Uiso 1 1 calc R . .
C21 C 0.4077(7) 1.0944(6) 0.1265(5) 0.0345(13) Uani 1 1 d . . .
H21 H 0.4405 1.1799 0.1767 0.041 Uiso 1 1 calc R . .
C7 C 0.2486(8) 0.4814(7) 0.2048(6) 0.0459(16) Uani 1 1 d . . .
H7A H 0.2039 0.3957 0.2225 0.069 Uiso 1 1 calc R . .
H7B H 0.1952 0.5274 0.2043 0.069 Uiso 1 1 calc R . .
H7C H 0.3522 0.5408 0.2659 0.069 Uiso 1 1 calc R . .
C25 C 0.7964(8) 0.3450(7) 0.5576(7) 0.0461(16) Uani 1 1 d . . .
H25 H 0.7242 0.2518 0.5389 0.055 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.777(5) . ?
S1 C1 1.773(5) . ?
O2 C14 1.242(6) . ?
O1 C2 1.241(6) . ?
N2 H2 0.8600 . ?
N2 C10 1.334(6) . ?
N2 C23 1.429(6) . ?
N1 H1 0.8600 . ?
N1 C6 1.341(6) . ?
N1 C17 1.416(6) . ?
C9 C10 1.389(6) . ?
C9 C14 1.436(7) . ?
C6 C1 1.391(6) . ?
C6 C5 1.506(7) . ?
C10 C11 1.501(6) . ?
C1 C2 1.434(7) . ?
C14 C13 1.516(7) . ?
C17 C18 1.381(7) . ?
C17 C22 1.388(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.534(6) . ?
C2 C3 1.517(7) . ?
C12 C13 1.532(7) . ?
C12 C16 1.530(7) . ?
C12 C15 1.536(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C23 C28 1.385(7) . ?
C23 C24 1.382(8) . ?
C28 H28 0.9300 . ?
C28 C27 1.401(8) . ?
C4 C3 1.529(7) . ?
C4 C5 1.532(7) . ?
C4 C8 1.532(8) . ?
C4 C7 1.518(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.373(8) . ?
C19 C18 1.385(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.380(8) . ?
C18 H18 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.386(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(10) . ?
C26 C25 1.381(10) . ?
C27 H27 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C21 H21 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C25 H25 0.9300 . ?

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 C9 106.0(2) . . ?
C10 N2 H2 116.3 . . ?
C10 N2 C23 127.3(4) . . ?
C23 N2 H2 116.3 . . ?
C6 N1 H1 115.2 . . ?
C6 N1 C17 129.7(4) . . ?
C17 N1 H1 115.2 . . ?
C10 C9 S1 119.7(4) . . ?
C10 C9 C14 121.8(4) . . ?
C14 C9 S1 118.4(4) . . ?
N1 C6 C1 120.0(4) . . ?
N1 C6 C5 120.0(4) . . ?
C1 C6 C5 120.0(4) . . ?
N2 C10 C9 121.0(4) . . ?
N2 C10 C11 119.4(4) . . ?
C9 C10 C11 119.6(4) . . ?
C6 C1 S1 120.0(4) . . ?
C6 C1 C2 121.9(4) . . ?
C2 C1 S1 118.0(4) . . ?
O2 C14 C9 123.2(5) . . ?
O2 C14 C13 118.4(4) . . ?
C9 C14 C13 118.4(4) . . ?
C18 C17 N1 123.8(5) . . ?
C18 C17 C22 119.1(5) . . ?
C22 C17 N1 116.8(4) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.6(4) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
O1 C2 C1 123.4(5) . . ?
O1 C2 C3 118.6(4) . . ?
C1 C2 C3 118.0(4) . . ?
C11 C12 C15 110.1(4) . . ?
C13 C12 C11 107.6(4) . . ?
C13 C12 C15 110.3(4) . . ?
C16 C12 C11 109.0(4) . . ?
C16 C12 C13 110.1(4) . . ?
C16 C12 C15 109.8(4) . . ?
C14 C13 C12 115.5(4) . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C28 C23 N2 121.4(5) . . ?
C24 C23 N2 117.8(5) . . ?
C24 C23 C28 120.5(5) . . ?
C23 C28 H28 120.7 . . ?
C23 C28 C27 118.6(5) . . ?
C27 C28 H28 120.7 . . ?
C3 C4 C5 107.8(4) . . ?
C3 C4 C8 109.6(4) . . ?
C5 C4 C8 108.4(4) . . ?
C7 C4 C3 110.6(5) . . ?
C7 C4 C5 111.0(5) . . ?
C7 C4 C8 109.4(5) . . ?
C2 C3 C4 114.3(4) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.1(6) . . ?
C25 C24 H24 119.9 . . ?
C6 C5 C4 112.6(4) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(5) . . ?
C21 C20 H20 120.3 . . ?
C17 C18 C19 120.2(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.2(5) . . ?
C21 C22 H22 119.9 . . ?
C27 C26 H26 120.0 . . ?
C27 C26 C25 119.9(5) . . ?
C25 C26 H26 120.0 . . ?
C28 C27 H27 119.6 . . ?
C26 C27 C28 120.8(6) . . ?
C26 C27 H27 119.6 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C20 C21 C22 120.3(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(6) . . ?
C26 C25 H25 120.0 . . ?

