# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b140430b_0m
_database_code_depnum_ccdc_archive 'CCDC 1009375'
_audit_update_record             
;
2014-06-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N3 O2 S'
_chemical_formula_sum            'C20 H23 N3 O2 S'
_chemical_formula_weight         369.47

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M_alt 'P 21/n'
_symmetry_space_group_name_H-M_hall '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.2469(6)
_cell_length_b                   12.1137(7)
_cell_length_c                   17.1803(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.893(2)
_cell_angle_gamma                90.00
_cell_volume                     1895.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8946
_exptl_absorpt_correction_T_max  0.9630
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41832
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         31.11
_reflns_number_total             6070
_reflns_number_gt                4446
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.8880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64971(5) 0.37197(3) 0.50452(2) 0.02547(11) Uani 1 1 d . . .
O1 O 0.67475(14) 0.48836(9) 0.50305(7) 0.0334(3) Uani 1 1 d . . .
O2 O 0.57747(14) 0.32494(9) 0.56329(6) 0.0315(3) Uani 1 1 d . . .
N1 N 0.54923(15) 0.34144(10) 0.41719(7) 0.0244(3) Uani 1 1 d . . .
N2 N 0.50908(15) 0.23021(10) 0.40936(7) 0.0242(3) Uani 1 1 d . . .
N3 N 0.60200(15) 0.49533(10) 0.33919(8) 0.0252(3) Uani 1 1 d . . .
H3 H 0.603(2) 0.5297(16) 0.3775(12) 0.030 Uiso 1 1 d . . .
C1 C 0.55709(15) 0.38968(11) 0.34394(8) 0.0198(3) Uani 1 1 d . . .
C2 C 0.51144(15) 0.30908(11) 0.28907(8) 0.0198(3) Uani 1 1 d . . .
H2 H 0.4998 0.3157 0.2344 0.024 Uiso 1 1 calc R . .
C3 C 0.48556(15) 0.21368(11) 0.33243(8) 0.0192(3) Uani 1 1 d . . .
C4 C 0.43893(15) 0.10422(11) 0.30097(9) 0.0204(3) Uani 1 1 d . . .
C5 C 0.39079(18) 0.08857(12) 0.22084(9) 0.0280(3) Uani 1 1 d . . .
H5 H 0.3842 0.1487 0.1867 0.034 Uiso 1 1 calc R . .
C6 C 0.3522(2) -0.01601(14) 0.19086(11) 0.0353(4) Uani 1 1 d . . .
H6 H 0.3192 -0.0255 0.1370 0.042 Uiso 1 1 calc R . .
C7 C 0.36304(19) -0.10587(13) 0.24117(11) 0.0336(4) Uani 1 1 d . . .
H7 H 0.3383 -0.1759 0.2211 0.040 Uiso 1 1 calc R . .
C8 C 0.41049(18) -0.09159(12) 0.32098(11) 0.0295(3) Uani 1 1 d . . .
H8 H 0.4178 -0.1521 0.3547 0.035 Uiso 1 1 calc R . .
C9 C 0.44736(16) 0.01277(12) 0.35124(9) 0.0237(3) Uani 1 1 d . . .
H9 H 0.4779 0.0220 0.4053 0.028 Uiso 1 1 calc R . .
C10 C 0.61513(16) 0.55449(11) 0.26609(8) 0.0217(3) Uani 1 1 d . . .
C11 C 0.71654(18) 0.49220(13) 0.22027(10) 0.0309(3) Uani 1 1 d . . .
H11A H 0.8082 0.4776 0.2543 0.046 Uiso 1 1 calc R . .
H11B H 0.7339 0.5361 0.1763 0.046 Uiso 1 1 calc R . .
H11C H 0.6715 0.4237 0.2013 0.046 Uiso 1 1 calc R . .
C12 C 0.46457(18) 0.57247(14) 0.21535(11) 0.0338(4) Uani 1 1 d . . .
H12A H 0.4195 0.5023 0.2010 0.051 Uiso 1 1 calc R . .
H12B H 0.4756 0.6122 0.1684 0.051 Uiso 1 1 calc R . .
H12C H 0.4039 0.6142 0.2447 0.051 Uiso 1 1 calc R . .
C13 C 0.6834(2) 0.66595(13) 0.29264(11) 0.0332(4) Uani 1 1 d . . .
H13A H 0.6228 0.7032 0.3244 0.050 Uiso 1 1 calc R . .
H13B H 0.6909 0.7101 0.2471 0.050 Uiso 1 1 calc R . .
H13C H 0.7795 0.6547 0.3231 0.050 Uiso 1 1 calc R . .
C14 C 0.81708(18) 0.30322(12) 0.50528(8) 0.0254(3) Uani 1 1 d . . .
C15 C 0.83598(19) 0.19683(13) 0.53520(10) 0.0300(3) Uani 1 1 d . . .
H15 H 0.7596 0.1610 0.5537 0.036 Uiso 1 1 calc R . .
C16 C 0.96994(19) 0.14444(13) 0.53726(10) 0.0309(3) Uani 1 1 d . . .
H16 H 0.9828 0.0733 0.5576 0.037 Uiso 1 1 calc R . .
C17 C 1.08516(18) 0.19615(14) 0.50961(9) 0.0306(3) Uani 1 1 d . . .
C18 C 1.0630(2) 0.30193(16) 0.47912(12) 0.0406(4) Uani 1 1 d . . .
H18 H 1.1389 0.3374 0.4600 0.049 Uiso 1 1 calc R . .
C19 C 0.9299(2) 0.35605(14) 0.47656(11) 0.0376(4) Uani 1 1 d . . .
H19 H 0.9166 0.4269 0.4558 0.045 Uiso 1 1 calc R . .
C20 C 1.2310(2) 0.13935(17) 0.51272(12) 0.0412(4) Uani 1 1 d . . .
H20A H 1.3084 0.1929 0.5226 0.062 Uiso 1 1 calc R . .
H20B H 1.2335 0.1034 0.4632 0.062 Uiso 1 1 calc R . .
H20C H 1.2440 0.0855 0.5544 0.062 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 O2 1.4220(11) . ?
S1 O1 1.4296(11) . ?
S1 N1 1.6649(13) . ?
S1 C14 1.7556(17) . ?
N1 N2 1.3980(16) . ?
N1 C1 1.4007(17) . ?
N2 C3 1.3173(18) . ?
N3 C1 1.3522(18) . ?
N3 C10 1.4691(18) . ?
N3 H3 0.78(2) . ?
C1 C2 1.3724(19) . ?
C2 C3 1.4174(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.4683(19) . ?
C4 C5 1.385(2) . ?
C4 C9 1.3986(19) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.524(2) . ?
C10 C12 1.526(2) . ?
C10 C13 1.527(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.385(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 C20 1.507(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 120.33(7) . . ?
O2 S1 N1 107.06(7) . . ?
O1 S1 N1 105.67(6) . . ?
O2 S1 C14 109.01(7) . . ?
O1 S1 C14 108.83(8) . . ?
N1 S1 C14 104.84(7) . . ?
N2 N1 C1 111.69(11) . . ?
N2 N1 S1 113.50(9) . . ?
C1 N1 S1 127.58(10) . . ?
C3 N2 N1 103.80(11) . . ?
C1 N3 C10 125.77(12) . . ?
C1 N3 H3 114.4(14) . . ?
C10 N3 H3 118.2(14) . . ?
N3 C1 C2 133.89(13) . . ?
N3 C1 N1 120.86(12) . . ?
C2 C1 N1 105.25(12) . . ?
C1 C2 C3 106.19(12) . . ?
C1 C2 H2 126.9 . . ?
C3 C2 H2 126.9 . . ?
N2 C3 C2 112.93(12) . . ?
N2 C3 C4 119.61(12) . . ?
C2 C3 C4 127.46(13) . . ?
C5 C4 C9 118.66(13) . . ?
C5 C4 C3 120.89(13) . . ?
C9 C4 C3 120.41(13) . . ?
C4 C5 C6 120.73(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.94(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.00(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.23(15) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.43(15) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
N3 C10 C11 110.41(12) . . ?
N3 C10 C12 110.90(12) . . ?
C11 C10 C12 110.95(14) . . ?
N3 C10 C13 105.47(12) . . ?
C11 C10 C13 109.43(12) . . ?
C12 C10 C13 109.53(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.44(16) . . ?
C19 C14 S1 119.67(12) . . ?
C15 C14 S1 119.89(12) . . ?
C16 C15 C14 119.32(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.29(15) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 118.31(16) . . ?
C18 C17 C20 120.58(16) . . ?
C16 C17 C20 121.11(16) . . ?
C17 C18 C19 121.39(16) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C14 C19 C18 119.24(16) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 N2 -48.21(12) . . . . ?
O1 S1 N1 N2 -177.61(10) . . . . ?
C14 S1 N1 N2 67.49(11) . . . . ?
O2 S1 N1 C1 164.32(12) . . . . ?
O1 S1 N1 C1 34.92(15) . . . . ?
C14 S1 N1 C1 -79.98(14) . . . . ?
C1 N1 N2 C3 -3.22(16) . . . . ?
S1 N1 N2 C3 -155.92(10) . . . . ?
C10 N3 C1 C2 -0.7(3) . . . . ?
C10 N3 C1 N1 179.78(13) . . . . ?
N2 N1 C1 N3 -176.37(13) . . . . ?
S1 N1 C1 N3 -28.4(2) . . . . ?
N2 N1 C1 C2 4.01(16) . . . . ?
S1 N1 C1 C2 151.96(11) . . . . ?
N3 C1 C2 C3 177.40(16) . . . . ?
N1 C1 C2 C3 -3.05(15) . . . . ?
N1 N2 C3 C2 1.19(16) . . . . ?
N1 N2 C3 C4 -179.35(12) . . . . ?
C1 C2 C3 N2 1.22(17) . . . . ?
C1 C2 C3 C4 -178.18(13) . . . . ?
N2 C3 C4 C5 169.55(14) . . . . ?
C2 C3 C4 C5 -11.1(2) . . . . ?
N2 C3 C4 C9 -12.8(2) . . . . ?
C2 C3 C4 C9 166.61(14) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 177.44(15) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C4 -1.0(2) . . . . ?
C5 C4 C9 C8 1.1(2) . . . . ?
C3 C4 C9 C8 -176.67(13) . . . . ?
C1 N3 C10 C11 -56.6(2) . . . . ?
C1 N3 C10 C12 66.81(19) . . . . ?
C1 N3 C10 C13 -174.70(14) . . . . ?
O2 S1 C14 C19 -156.15(13) . . . . ?
O1 S1 C14 C19 -23.18(16) . . . . ?
N1 S1 C14 C19 89.50(14) . . . . ?
O2 S1 C14 C15 23.30(15) . . . . ?
O1 S1 C14 C15 156.28(13) . . . . ?
N1 S1 C14 C15 -91.04(13) . . . . ?
C19 C14 C15 C16 1.0(2) . . . . ?
S1 C14 C15 C16 -178.42(13) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C15 C16 C17 C20 179.37(16) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C20 C17 C18 C19 -179.29(18) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
S1 C14 C19 C18 178.51(14) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        31.11
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.062
