# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_rh-1
_database_code_depnum_ccdc_archive 'CCDC 980304'
_audit_update_record             
;
2014-01-07 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H21 N3 O4 S2'
_chemical_formula_sum            'C18 H21 N3 O4 S2'
_chemical_melting_point          ?
_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         407.
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9629(13)
_cell_length_b                   10.231(3)
_cell_length_c                   14.781(2)
_cell_angle_alpha                102.726(18)
_cell_angle_beta                 97.404(16)
_cell_angle_gamma                94.658(18)
_cell_volume                     1012.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1413
_cell_measurement_theta_min      2.9633
_cell_measurement_theta_max      28.9220
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428.0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6963
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         28.99
_reflns_number_total             4036
_reflns_number_gt                2182
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0061P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.002
_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
S2 S -0.41382(8) -0.16841(8) 0.34303(5) 0.0499(2) Uani 1 1 d . . .
S1 S -0.80614(9) -0.30033(9) 0.23261(6) 0.0689(3) Uani 1 1 d . . .
O1 O 0.0550(2) 0.20322(17) 0.06618(11) 0.0462(5) Uani 1 1 d . . .
N2 N -0.3507(2) -0.0972(2) 0.18390(14) 0.0411(6) Uani 1 1 d . . .
O4 O -0.7955(2) -0.22355(19) 0.50955(12) 0.0547(5) Uani 1 1 d . . .
O2 O -0.2408(2) 0.12307(19) -0.00614(12) 0.0570(6) Uani 1 1 d . . .
N1 N 0.6894(3) 0.4063(2) 0.21014(15) 0.0511(6) Uani 1 1 d . . .
N3 N -0.5327(2) -0.1695(2) 0.17124(14) 0.0440(6) Uani 1 1 d . . .
H3 H -0.6073 -0.1853 0.1180 0.053 Uiso 1 1 calc R . .
O3 O -0.7340(3) -0.0486(2) 0.44443(14) 0.0631(6) Uani 1 1 d . . .
C12 C -0.1277(3) 0.0392(3) 0.12566(17) 0.0373(6) Uani 1 1 d . . .
C9 C 0.2090(3) 0.2114(3) 0.13645(17) 0.0369(6) Uani 1 1 d . . .
C8 C 0.2008(3) 0.1314(2) 0.20077(16) 0.0350(6) Uani 1 1 d . . .
C11 C 0.0262(3) 0.0435(3) 0.19231(17) 0.0385(6) Uani 1 1 d . . .
H11 H 0.0181 -0.0123 0.2339 0.046 Uiso 1 1 calc R . .
C5 C 0.5304(3) 0.3167(3) 0.20648(17) 0.0411(7) Uani 1 1 d . . .
C7 C 0.3635(3) 0.1465(3) 0.26871(17) 0.0437(7) Uani 1 1 d . . .
H7 H 0.3632 0.0950 0.3133 0.052 Uiso 1 1 calc R . .
C17 C -0.6985(3) -0.1557(3) 0.45815(18) 0.0464(7) Uani 1 1 d . . .
C10 C 0.3667(3) 0.3022(3) 0.13758(17) 0.0422(7) Uani 1 1 d . . .
H10 H 0.3648 0.3536 0.0929 0.051 Uiso 1 1 calc R . .
C3 C 0.6837(3) 0.5130(3) 0.15652(19) 0.0560(9) Uani 1 1 d . . .
H3A H 0.5503 0.5329 0.1443 0.067 Uiso 1 1 calc R . .
H3B H 0.7607 0.5946 0.1944 0.067 Uiso 1 1 calc R . .
C2 C 0.8709(3) 0.4096(3) 0.27370(19) 0.0545(8) Uani 1 1 d . . .
H2A H 0.9803 0.4397 0.2460 0.065 Uiso 1 1 calc R . .
H2B H 0.8868 0.3192 0.2814 0.065 Uiso 1 1 calc R . .
C1 C 0.8722(4) 0.5011(3) 0.3676(2) 0.0812(11) Uani 1 1 d . . .
H1A H 0.8500 0.5897 0.3600 0.122 Uiso 1 1 calc R . .
H1B H 0.9963 0.5054 0.4055 0.122 Uiso 1 1 calc R . .
H1C H 0.7712 0.4671 0.3976 0.122 Uiso 1 1 calc R . .
C14 C -0.3131(3) -0.0435(3) 0.11746(18) 0.0435(7) Uani 1 1 d . . .
H14 H -0.4040 -0.0568 0.0634 0.052 Uiso 1 1 calc R . .
C16 C -0.5394(3) -0.2351(3) 0.42384(19) 0.0561(8) Uani 1 1 d . . .
H16A H -0.5956 -0.3267 0.3939 0.067 Uiso 1 1 calc R . .
H16B H -0.4457 -0.2389 0.4775 0.067 Uiso 1 1 calc R . .
C6 C 0.5239(3) 0.2346(3) 0.27217(18) 0.0457(7) Uani 1 1 d . . .
H6 H 0.6308 0.2409 0.3183 0.055 Uiso 1 1 calc R . .
C13 C -0.1157(3) 0.1196(3) 0.05712(17) 0.0408(7) Uani 1 1 d . . .
C15 C -0.5915(3) -0.2143(3) 0.24284(17) 0.0432(7) Uani 1 1 d . . .
C4 C 0.7586(4) 0.4740(3) 0.0666(2) 0.0800(10) Uani 1 1 d . . .
H4A H 0.6732 0.4004 0.0256 0.120 Uiso 1 1 calc R . .
H4B H 0.8867 0.4469 0.0777 0.120 Uiso 1 1 calc R . .
H4C H 0.7648 0.5495 0.0378 0.120 Uiso 1 1 calc R . .
C18 C -0.9547(4) -0.1594(3) 0.5473(2) 0.0688(9) Uani 1 1 d . . .
H18A H -1.0311 -0.1279 0.4993 0.103 Uiso 1 1 calc R . .
H18B H -0.9037 -0.0845 0.5987 0.103 Uiso 1 1 calc R . .
H18C H -1.0352 -0.2232 0.5690 0.103 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
S2 C15 1.753(2) . ?
S2 C16 1.786(2) . ?
S1 C15 1.643(2) . ?
O1 C9 1.377(2) . ?
O1 C13 1.380(2) . ?
N2 C14 1.272(3) . ?
N2 N3 1.383(2) . ?
O4 C17 1.343(3) . ?
O4 C18 1.445(3) . ?
O2 C13 1.202(3) . ?
N1 C5 1.366(3) . ?
N1 C2 1.467(3) . ?
N1 C3 1.484(3) . ?
N3 C15 1.339(3) . ?
N3 H3 0.8600 . ?
O3 C17 1.196(3) . ?
C12 C11 1.349(3) . ?
C12 C13 1.445(3) . ?
C12 C14 1.461(3) . ?
C9 C10 1.375(3) . ?
C9 C8 1.388(3) . ?
C8 C7 1.388(3) . ?
C8 C11 1.426(3) . ?
C11 H11 0.9300 . ?
C5 C10 1.402(3) . ?
C5 C6 1.420(3) . ?
C7 C6 1.366(3) . ?
C7 H7 0.9300 . ?
C17 C16 1.501(4) . ?
C10 H10 0.9300 . ?
C3 C4 1.476(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.492(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 H6 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
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
C15 S2 C16 100.00(11) . . ?
C9 O1 C13 122.68(18) . . ?
C14 N2 N3 116.10(19) . . ?
C17 O4 C18 115.1(2) . . ?
C5 N1 C2 121.6(2) . . ?
C5 N1 C3 122.12(19) . . ?
C2 N1 C3 116.04(18) . . ?
C15 N3 N2 119.23(19) . . ?
C15 N3 H3 120.4 . . ?
N2 N3 H3 120.4 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 C14 123.8(2) . . ?
C13 C12 C14 115.9(2) . . ?
C10 C9 O1 115.7(2) . . ?
C10 C9 C8 123.6(2) . . ?
O1 C9 C8 120.70(18) . . ?
C7 C8 C9 116.4(2) . . ?
C7 C8 C11 126.1(2) . . ?
C9 C8 C11 117.5(2) . . ?
C12 C11 C8 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C8 C11 H11 119.1 . . ?
N1 C5 C10 121.3(2) . . ?
N1 C5 C6 121.5(2) . . ?
C10 C5 C6 117.2(2) . . ?
C6 C7 C8 122.1(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
O3 C17 O4 124.5(3) . . ?
O3 C17 C16 126.9(2) . . ?
O4 C17 C16 108.7(2) . . ?
C9 C10 C5 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C4 C3 N1 112.7(3) . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N1 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C2 C1 112.0(2) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C14 C12 120.3(2) . . ?
N2 C14 H14 119.9 . . ?
C12 C14 H14 119.9 . . ?
C17 C16 S2 114.39(19) . . ?
C17 C16 H16A 108.7 . . ?
S2 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
S2 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O2 C13 O1 116.5(2) . . ?
O2 C13 C12 126.6(2) . . ?
O1 C13 C12 116.9(2) . . ?
N3 C15 S1 121.71(18) . . ?
N3 C15 S2 111.39(15) . . ?
S1 C15 S2 126.90(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

