# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20150528ngd_0m
_database_code_depnum_ccdc_archive 'CCDC 1432307'
_audit_update_record             
;
2015-10-20 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_weight         353.42

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   '

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

_cell_length_a                   7.326(5)
_cell_length_b                   10.134(7)
_cell_length_c                   12.489(8)
_cell_angle_alpha                80.774(11)
_cell_angle_beta                 82.540(12)
_cell_angle_gamma                77.770(11)
_cell_volume                     890.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2040
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4938
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3122
_reflns_number_gt                2417
_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)+(0.0536P)²+0.2674P] 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         3122
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.3973(3) 0.6592(2) 0.22175(18) 0.0530(5) Uani 1 1 d . . .
C2 C 0.5603(5) 0.7685(3) 0.3097(3) 0.0982(11) Uani 1 1 d . . .
H2A H 0.5016 0.8208 0.3679 0.118 Uiso 1 1 calc R . .
H2B H 0.6719 0.8025 0.2771 0.118 Uiso 1 1 calc R . .
C3 C 0.6105(4) 0.6217(3) 0.3531(2) 0.0720(7) Uani 1 1 d . . .
H3A H 0.7433 0.5862 0.3370 0.086 Uiso 1 1 calc R . .
H3B H 0.5773 0.6058 0.4312 0.086 Uiso 1 1 calc R . .
C4 C 0.4968(3) 0.4234(2) 0.31260(18) 0.0558(6) Uani 1 1 d . . .
C5 C 0.3767(3) 0.3692(2) 0.24861(17) 0.0494(5) Uani 1 1 d . . .
C6 C 0.4470(3) 0.3143(2) 0.15895(16) 0.0469(5) Uani 1 1 d . . .
C7 C 0.6489(3) 0.3074(3) 0.11353(19) 0.0647(6) Uani 1 1 d . . .
H7A H 0.7129 0.3440 0.1608 0.097 Uiso 1 1 calc R . .
H7B H 0.6545 0.3596 0.0423 0.097 Uiso 1 1 calc R . .
H7C H 0.7079 0.2142 0.1085 0.097 Uiso 1 1 calc R . .
C8 C 0.3316(3) 0.2595(2) 0.09381(16) 0.0462(5) Uani 1 1 d . . .
C9 C 0.2141(4) 0.3457(3) 0.0245(2) 0.0670(7) Uani 1 1 d . . .
H9 H 0.2030 0.4394 0.0205 0.080 Uiso 1 1 calc R . .
C10 C 0.1114(4) 0.2948(3) -0.0399(2) 0.0808(8) Uani 1 1 d . . .
H10 H 0.0329 0.3540 -0.0869 0.097 Uiso 1 1 calc R . .
C11 C 0.1266(4) 0.1575(4) -0.0335(3) 0.0850(9) Uani 1 1 d . . .
H11 H 0.0581 0.1230 -0.0763 0.102 Uiso 1 1 calc R . .
C12 C 0.2414(5) 0.0709(3) 0.0352(3) 0.0839(9) Uani 1 1 d . . .
H12 H 0.2497 -0.0227 0.0400 0.101 Uiso 1 1 calc R . .
C13 C 0.3455(4) 0.1212(2) 0.0977(2) 0.0658(7) Uani 1 1 d . . .
H13 H 0.4261 0.0610 0.1431 0.079 Uiso 1 1 calc R . .
C14 C 0.1429(3) 0.2660(2) 0.41776(17) 0.0498(5) Uani 1 1 d . . .
C15 C 0.2571(4) 0.1384(2) 0.4223(2) 0.0655(6) Uani 1 1 d . . .
H15 H 0.3434 0.1168 0.3632 0.079 Uiso 1 1 calc R . .
C16 C 0.2448(4) 0.0433(3) 0.5127(2) 0.0646(6) Uani 1 1 d . . .
H16 H 0.3236 -0.0419 0.5140 0.078 Uiso 1 1 calc R . .
C17 C 0.1188(3) 0.0707(3) 0.60168(19) 0.0594(6) Uani 1 1 d . . .
C18 C 0.0069(4) 0.1983(3) 0.5964(2) 0.0734(7) Uani 1 1 d . . .
H18 H -0.0788 0.2198 0.6558 0.088 Uiso 1 1 calc R . .
C19 C 0.0170(3) 0.2952(3) 0.5066(2) 0.0641(6) Uani 1 1 d . . .
H19 H -0.0613 0.3805 0.5058 0.077 Uiso 1 1 calc R . .
C20 C 0.1096(5) -0.0349(3) 0.7002(2) 0.0883(9) Uani 1 1 d . . .
H20A H 0.1371 -0.1239 0.6778 0.133 Uiso 1 1 calc R . .
H20B H -0.0140 -0.0194 0.7381 0.133 Uiso 1 1 calc R . .
H20C H 0.1998 -0.0289 0.7476 0.133 Uiso 1 1 calc R . .
N1 N 0.4967(3) 0.56160(18) 0.29417(14) 0.0537(5) Uani 1 1 d . . .
O1 O 0.2910(3) 0.64496(16) 0.16162(14) 0.0678(5) Uani 1 1 d . . .
O2 O 0.4339(3) 0.78044(16) 0.23004(15) 0.0723(5) Uani 1 1 d . . .
O3 O 0.5894(3) 0.35258(18) 0.38080(15) 0.0849(6) Uani 1 1 d . . .
S1 S 0.13757(9) 0.39010(6) 0.30018(5) 0.0616(2) Uani 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
C1 O1 1.194(3) . ?
C1 O2 1.334(3) . ?
C1 N1 1.381(3) . ?
C2 O2 1.420(3) . ?
C2 C3 1.484(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.458(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.203(3) . ?
C4 N1 1.382(3) . ?
C4 C5 1.497(3) . ?
C5 C6 1.326(3) . ?
C5 S1 1.767(3) . ?
C6 C8 1.485(3) . ?
C6 C7 1.505(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.373(3) . ?
C8 C13 1.378(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.376(3) . ?
C14 C15 1.380(3) . ?
C14 S1 1.773(2) . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(4) . ?
C17 C20 1.500(4) . ?
C18 C19 1.373(4) . ?
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
O1 C1 O2 122.8(2) . . ?
O1 C1 N1 128.5(2) . . ?
O2 C1 N1 108.69(19) . . ?
O2 C2 C3 107.2(2) . . ?
O2 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
O2 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C2 101.9(2) . . ?
N1 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N1 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
O3 C4 N1 118.9(2) . . ?
O3 C4 C5 122.9(2) . . ?
N1 C4 C5 118.18(18) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 S1 123.95(17) . . ?
C4 C5 S1 114.56(16) . . ?
C5 C6 C8 122.7(2) . . ?
C5 C6 C7 122.2(2) . . ?
C8 C6 C7 115.04(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.2(2) . . ?
C9 C8 C6 120.74(19) . . ?
C13 C8 C6 121.0(2) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C19 C14 C15 118.3(2) . . ?
C19 C14 S1 118.00(18) . . ?
C15 C14 S1 123.55(18) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 117.1(2) . . ?
C18 C17 C20 122.5(3) . . ?
C16 C17 C20 120.4(3) . . ?
C17 C18 C19 122.3(2) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
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 . . ?
C1 N1 C4 127.45(18) . . ?
C1 N1 C3 111.22(19) . . ?
C4 N1 C3 121.33(19) . . ?
C1 O2 C2 111.0(2) . . ?
C5 S1 C14 102.33(10) . . ?

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 C2 C3 N1 -2.2(3) . . . . ?
O3 C4 C5 C6 -84.9(3) . . . . ?
N1 C4 C5 C6 96.9(3) . . . . ?
O3 C4 C5 S1 96.9(3) . . . . ?
N1 C4 C5 S1 -81.2(2) . . . . ?
C4 C5 C6 C8 179.92(18) . . . . ?
S1 C5 C6 C8 -2.2(3) . . . . ?
C4 C5 C6 C7 -2.3(3) . . . . ?
S1 C5 C6 C7 175.59(17) . . . . ?
C5 C6 C8 C9 77.8(3) . . . . ?
C7 C6 C8 C9 -100.1(3) . . . . ?
C5 C6 C8 C13 -105.0(3) . . . . ?
C7 C6 C8 C13 77.1(3) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
C6 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C11 C12 C13 C8 1.6(4) . . . . ?
C9 C8 C13 C12 -1.2(4) . . . . ?
C6 C8 C13 C12 -178.5(2) . . . . ?
C19 C14 C15 C16 0.2(4) . . . . ?
S1 C14 C15 C16 -175.06(18) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C15 C16 C17 C20 -179.4(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C20 C17 C18 C19 179.3(2) . . . . ?
C17 C18 C19 C14 -0.2(4) . . . . ?
C15 C14 C19 C18 -0.3(4) . . . . ?
S1 C14 C19 C18 175.29(19) . . . . ?
O1 C1 N1 C4 0.8(4) . . . . ?
O2 C1 N1 C4 179.1(2) . . . . ?
O1 C1 N1 C3 -179.6(3) . . . . ?
O2 C1 N1 C3 -1.3(3) . . . . ?
O3 C4 N1 C1 -178.5(2) . . . . ?
C5 C4 N1 C1 -0.2(3) . . . . ?
O3 C4 N1 C3 1.9(4) . . . . ?
C5 C4 N1 C3 -179.8(2) . . . . ?
C2 C3 N1 C1 2.1(3) . . . . ?
C2 C3 N1 C4 -178.2(2) . . . . ?
O1 C1 O2 C2 178.2(3) . . . . ?
N1 C1 O2 C2 -0.2(3) . . . . ?
C3 C2 O2 C1 1.6(3) . . . . ?
C6 C5 S1 C14 108.3(2) . . . . ?
C4 C5 S1 C14 -73.66(17) . . . . ?
C19 C14 S1 C5 145.92(18) . . . . ?
C15 C14 S1 C5 -38.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_20150925ngd2_0m
_database_code_depnum_ccdc_archive 'CCDC 1432338'
_audit_update_record             
;
2015-10-20 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O3 S'
_chemical_formula_weight         395.50
_chemical_absolute_configuration ad

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           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.5980(8)
_cell_length_b                   5.7831(3)
_cell_length_c                   14.8716(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.469(2)
_cell_angle_gamma                90.00
_cell_volume                     1088.34(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4514
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7583
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3727
_reflns_number_gt                3350
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0833P)²+0.0369P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_number_reflns         3727
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3121(3) 0.5695(6) 0.4025(2) 0.0877(10) Uani 1 1 d . . .
H1 H 0.2769 0.7039 0.4075 0.105 Uiso 1 1 calc R . .
C2 C 0.3396(4) 0.5361(8) 0.3229(3) 0.1092(14) Uani 1 1 d . . .
H2 H 0.3224 0.6474 0.2744 0.131 Uiso 1 1 calc R . .
C3 C 0.3927(4) 0.3371(8) 0.3150(3) 0.1001(12) Uani 1 1 d . . .
H3 H 0.4127 0.3162 0.2620 0.120 Uiso 1 1 calc R . .
C4 C 0.4148(3) 0.1777(8) 0.3828(3) 0.0964(11) Uani 1 1 d . . .
H4 H 0.4488 0.0427 0.3763 0.116 Uiso 1 1 calc R . .
C5 C 0.3880(2) 0.2081(6) 0.4649(2) 0.0776(8) Uani 1 1 d . . .
H5 H 0.4052 0.0947 0.5125 0.093 Uiso 1 1 calc R . .
C6 C 0.33630(19) 0.4057(6) 0.47460(18) 0.0637(6) Uani 1 1 d . . .
C7 C 0.3056(2) 0.4439(7) 0.56127(18) 0.0700(8) Uani 1 1 d . . .
H7A H 0.3355 0.5886 0.5922 0.084 Uiso 1 1 calc R . .
H7B H 0.3344 0.3203 0.6076 0.084 Uiso 1 1 calc R . .
C8 C 0.18614(19) 0.4505(4) 0.53211(15) 0.0513(6) Uani 1 1 d . . .
H8 H 0.1568 0.5820 0.4891 0.062 Uiso 1 1 calc R . .
C9 C 0.1333(2) 0.2286(5) 0.4845(2) 0.0680(7) Uani 1 1 d . . .
H9A H 0.1038 0.2465 0.4148 0.082 Uiso 1 1 calc R . .
H9B H 0.1840 0.1027 0.5003 0.082 Uiso 1 1 calc R . .
C10 C 0.06590(19) 0.3124(4) 0.59915(16) 0.0498(5) Uani 1 1 d . . .
C11 C 0.17348(18) 0.6501(4) 0.67556(15) 0.0486(5) Uani 1 1 d . . .
C12 C 0.14843(19) 0.6370(4) 0.76470(16) 0.0513(6) Uani 1 1 d . . .
C13 C 0.0918(2) 0.8029(5) 0.7843(2) 0.0640(7) Uani 1 1 d . . .
H13 H 0.0704 0.9227 0.7396 0.077 Uiso 1 1 calc R . .
C14 C 0.0586(3) 0.8209(7) 0.8683(2) 0.0857(9) Uani 1 1 d . . .
H14A H 0.0779 0.9724 0.8975 0.103 Uiso 1 1 calc R . .
H14B H 0.0965 0.7064 0.9161 0.103 Uiso 1 1 calc R . .
C15 C -0.0586(4) 0.7856(12) 0.8422(4) 0.1308(18) Uani 1 1 d . . .
H15A H -0.0773 0.8303 0.8968 0.157 Uiso 1 1 calc R . .
H15B H -0.0966 0.8863 0.7886 0.157 Uiso 1 1 calc R . .
C16 C -0.0935(6) 0.5412(17) 0.8150(6) 0.212(4) Uani 1 1 d . . .
H16A H -0.0627 0.4846 0.7706 0.319 Uiso 1 1 calc R . .
H16B H -0.1691 0.5360 0.7852 0.319 Uiso 1 1 calc R . .
H16C H -0.0709 0.4463 0.8720 0.319 Uiso 1 1 calc R . .
C17 C 0.33410(19) 0.4136(4) 0.85236(13) 0.0499(5) Uani 1 1 d . . .
C18 C 0.3813(3) 0.2302(4) 0.82417(18) 0.0661(7) Uani 1 1 d . . .
H18 H 0.3412 0.1023 0.7942 0.079 Uiso 1 1 calc R . .
C19 C 0.4859(3) 0.2365(6) 0.8402(2) 0.0751(8) Uani 1 1 d . . .
H19 H 0.5165 0.1113 0.8210 0.090 Uiso 1 1 calc R . .
C20 C 0.5492(2) 0.4247(7) 0.88439(17) 0.0718(8) Uani 1 1 d . . .
C21 C 0.5008(2) 0.6099(5) 0.91026(18) 0.0667(7) Uani 1 1 d . . .
H21 H 0.5404 0.7395 0.9388 0.080 Uiso 1 1 calc R . .
C22 C 0.3947(2) 0.6042(5) 0.89412(18) 0.0604(6) Uani 1 1 d . . .
H22 H 0.3632 0.7305 0.9116 0.072 Uiso 1 1 calc R . .
C23 C 0.6669(3) 0.4268(11) 0.9061(3) 0.1084(14) Uani 1 1 d . . .
H23A H 0.6795 0.4544 0.8475 0.163 Uiso 1 1 calc R . .
H23B H 0.6966 0.2802 0.9327 0.163 Uiso 1 1 calc R . .
H23C H 0.6994 0.5472 0.9518 0.163 Uiso 1 1 calc R . .
N1 N 0.15170(14) 0.4592(3) 0.61483(12) 0.0460(4) Uani 1 1 d . . .
O1 O 0.05207(13) 0.1830(3) 0.52082(12) 0.0588(4) Uani 1 1 d . . .
O2 O 0.00846(13) 0.2998(3) 0.64408(12) 0.0588(4) Uani 1 1 d . . .
O3 O 0.21568(16) 0.8181(3) 0.65672(13) 0.0665(5) Uani 1 1 d . . .
S1 S 0.19953(5) 0.39380(11) 0.83970(4) 0.0637(2) Uani 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
C1 C6 1.378(4) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.317(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(4) . ?
C7 C8 1.521(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.469(3) . ?
C8 C9 1.514(4) . ?
C8 H8 0.9800 . ?
C9 O1 1.422(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.202(3) . ?
C10 O1 1.339(3) . ?
C10 N1 1.392(3) . ?
C11 O3 1.212(3) . ?
C11 N1 1.388(3) . ?
C11 C12 1.487(3) . ?
C12 C13 1.327(4) . ?
C12 S1 1.771(2) . ?
C13 C14 1.480(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.510(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.498(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.382(4) . ?
C17 C22 1.380(4) . ?
C17 S1 1.773(3) . ?
C18 C19 1.354(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(5) . ?
C20 C23 1.512(4) . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C6 C1 C2 120.6(4) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 121.5(3) . . ?
C1 C6 C7 120.2(3) . . ?
C6 C7 C8 111.14(19) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 100.33(19) . . ?
N1 C8 C7 113.38(17) . . ?
C9 C8 C7 112.7(2) . . ?
N1 C8 H8 110.0 . . ?
C9 C8 H8 110.0 . . ?
C7 C8 H8 110.0 . . ?
O1 C9 C8 106.3(2) . . ?
O1 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
O1 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O2 C10 O1 122.5(2) . . ?
O2 C10 N1 128.3(2) . . ?
O1 C10 N1 109.2(2) . . ?
O3 C11 N1 119.6(2) . . ?
O3 C11 C12 121.9(2) . . ?
N1 C11 C12 118.43(19) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 S1 124.1(2) . . ?
C11 C12 S1 115.89(18) . . ?
C12 C13 C14 128.1(3) . . ?
C12 C13 H13 115.9 . . ?
C14 C13 H13 115.9 . . ?
C13 C14 C15 113.2(3) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 113.4(5) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.9(2) . . ?
C18 C17 S1 119.6(2) . . ?
C22 C17 S1 121.5(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 117.4(3) . . ?
C21 C20 C23 120.6(4) . . ?
C19 C20 C23 122.0(3) . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 N1 C10 124.1(2) . . ?
C11 N1 C8 121.00(18) . . ?
C10 N1 C8 110.07(18) . . ?
C10 O1 C9 110.2(2) . . ?
C12 S1 C17 99.64(11) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_20150925ngd3_0m
_database_code_depnum_ccdc_archive 'CCDC 1432339'
_audit_update_record             
;
2015-10-20 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H29 N O3 S2'
_chemical_formula_weight         479.63

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.8698(16)
_cell_length_b                   13.2620(15)
_cell_length_c                   15.0271(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.583(4)
_cell_angle_gamma                90.00
_cell_volume                     2562.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6330
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9391
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17942
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4495
_reflns_number_gt                3272
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0838P)²+1.4428P] 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         4495
_refine_ls_number_parameters     295
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.006
_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
C1 C 0.2520(2) 0.3196(2) 0.5308(2) 0.0519(7) Uani 1 1 d . . .
C2 C 0.1547(3) 0.2765(3) 0.5247(2) 0.0672(9) Uani 1 1 d . . .
H2 H 0.1290 0.2494 0.4710 0.081 Uiso 1 1 calc R . .
C3 C 0.0958(3) 0.2739(3) 0.5991(2) 0.0706(9) Uani 1 1 d . . .
H3 H 0.0299 0.2451 0.5949 0.085 Uiso 1 1 calc R . .
C4 C 0.1323(3) 0.3129(2) 0.6796(2) 0.0618(8) Uani 1 1 d . . .
C5 C 0.2301(3) 0.3561(3) 0.6836(2) 0.0635(8) Uani 1 1 d . . .
H5 H 0.2560 0.3830 0.7372 0.076 Uiso 1 1 calc R . .
C6 C 0.2898(3) 0.3602(2) 0.6104(2) 0.0586(8) Uani 1 1 d . . .
H6 H 0.3552 0.3902 0.6144 0.070 Uiso 1 1 calc R . .
C7 C 0.0673(3) 0.3085(3) 0.7605(3) 0.0898(12) Uani 1 1 d . . .
H7A H 0.0009 0.3391 0.7469 0.135 Uiso 1 1 calc R . .
H7B H 0.1022 0.3442 0.8088 0.135 Uiso 1 1 calc R . .
H7C H 0.0575 0.2394 0.7773 0.135 Uiso 1 1 calc R . .
C8 C 0.4591(3) 0.3693(3) 0.2375(2) 0.0650(9) Uani 1 1 d . . .
H8 H 0.4317 0.3146 0.2674 0.078 Uiso 1 1 calc R . .
C9 C 0.4944(3) 0.3559(3) 0.1536(2) 0.0792(11) Uani 1 1 d . . .
H9 H 0.4900 0.2926 0.1270 0.095 Uiso 1 1 calc R . .
C10 C 0.5359(3) 0.4344(4) 0.1090(3) 0.0935(13) Uani 1 1 d . . .
H10 H 0.5609 0.4247 0.0525 0.112 Uiso 1 1 calc R . .
C11 C 0.5404(4) 0.5273(4) 0.1477(3) 0.0996(15) Uani 1 1 d . . .
H11 H 0.5685 0.5812 0.1173 0.119 Uiso 1 1 calc R . .
C12 C 0.5035(3) 0.5423(3) 0.2323(2) 0.0730(10) Uani 1 1 d . . .
H12 H 0.5058 0.6063 0.2576 0.088 Uiso 1 1 calc R . .
C13 C 0.4635(2) 0.4626(2) 0.27872(19) 0.0521(7) Uani 1 1 d . . .
C14 C 0.4310(2) 0.4783(2) 0.37331(19) 0.0531(7) Uani 1 1 d . . .
H14A H 0.4853 0.4524 0.4140 0.064 Uiso 1 1 calc R . .
H14B H 0.4250 0.5501 0.3842 0.064 Uiso 1 1 calc R . .
C15 C 0.2365(2) 0.4648(2) 0.35975(18) 0.0505(7) Uani 1 1 d . . .
C16 C 0.2337(3) 0.5678(2) 0.3190(2) 0.0625(8) Uani 1 1 d . . .
C17 C 0.2090(3) 0.5798(3) 0.2332(3) 0.0856(12) Uani 1 1 d . . .
H17 H 0.2008 0.6456 0.2127 0.103 Uiso 1 1 calc R . .
C18 C 0.1931(5) 0.4982(4) 0.1667(3) 0.119 Uani 1 1 d . . .
H18A H 0.2361 0.4415 0.1859 0.143 Uiso 1 1 calc R . .
H18B H 0.1212 0.4765 0.1679 0.143 Uiso 1 1 calc R . .
C19 C 0.2282(3) 0.6416(2) 0.4932(2) 0.0614(8) Uani 1 1 d . . .
C20 C 0.1298(3) 0.6066(3) 0.5103(3) 0.0709(10) Uani 1 1 d . . .
H20 H 0.0821 0.5940 0.4633 0.085 Uiso 1 1 calc R . .
C21 C 0.1023(3) 0.5905(3) 0.5965(3) 0.0769(10) Uani 1 1 d . . .
H21 H 0.0362 0.5661 0.6067 0.092 Uiso 1 1 calc R . .
C22 C 0.1699(3) 0.6093(3) 0.6681(3) 0.0738(10) Uani 1 1 d . . .
C23 C 0.2674(3) 0.6435(3) 0.6505(3) 0.0773(11) Uani 1 1 d . . .
H23 H 0.3147 0.6565 0.6978 0.093 Uiso 1 1 calc R . .
C24 C 0.2973(3) 0.6592(3) 0.5650(3) 0.0719(10) Uani 1 1 d . . .
H24 H 0.3642 0.6817 0.5552 0.086 Uiso 1 1 calc R . .
C25 C 0.1385(5) 0.5918(4) 0.7631(3) 0.1118(16) Uani 1 1 d . . .
H25A H 0.1836 0.5423 0.7910 0.168 Uiso 1 1 calc R . .
H25B H 0.0679 0.5682 0.7626 0.168 Uiso 1 1 calc R . .
H25C H 0.1441 0.6539 0.7958 0.168 Uiso 1 1 calc R . .
C26 C 0.2156(10) 0.5210(9) 0.0732(7) 0.241(5) Uani 1 1 d U . .
H26A H 0.2830 0.5537 0.0721 0.289 Uiso 1 1 calc R . .
H26B H 0.2200 0.4581 0.0407 0.289 Uiso 1 1 calc R . .
C27 C 0.1447(11) 0.5801(10) 0.0315(8) 0.270(5) Uani 1 1 d U . .
H27A H 0.0763 0.5586 0.0461 0.405 Uiso 1 1 calc R . .
H27B H 0.1517 0.5754 -0.0317 0.405 Uiso 1 1 calc R . .
H27C H 0.1553 0.6487 0.0503 0.405 Uiso 1 1 calc R . .
N1 N 0.33171(18) 0.42936(17) 0.39341(15) 0.0479(6) Uani 1 1 d . . .
O1 O 0.43899(18) 0.30355(19) 0.47538(16) 0.0744(7) Uani 1 1 d . . .
O2 O 0.2950(2) 0.24087(16) 0.37856(15) 0.0757(7) Uani 1 1 d . . .
O3 O 0.15803(17) 0.41597(17) 0.36440(14) 0.0645(6) Uani 1 1 d . . .
S1 S 0.33429(6) 0.31352(6) 0.44111(5) 0.0555(3) Uani 1 1 d . . .
S2 S 0.26687(10) 0.67424(7) 0.38554(8) 0.0861(4) Uani 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
C1 C2 1.376(5) . ?
C1 C6 1.380(4) . ?
C1 S1 1.753(3) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C7 1.507(5) . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.371(5) . ?
C8 C13 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.514(4) . ?
C14 N1 1.477(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O3 1.204(3) . ?
C15 N1 1.387(4) . ?
C15 C16 1.497(4) . ?
C16 C17 1.323(5) . ?
C16 S2 1.771(4) . ?
C17 C18 1.480(7) . ?
C17 H17 0.9300 . ?
C18 C26 1.478(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.384(5) . ?
C19 C24 1.386(5) . ?
C19 S2 1.768(4) . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(5) . ?
C22 C25 1.518(6) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.337(12) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 S1 1.695(2) . ?
O1 S1 1.427(2) . ?
O2 S1 1.423(2) . ?

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
C2 C1 C6 120.3(3) . . ?
C2 C1 S1 120.6(2) . . ?
C6 C1 S1 118.9(2) . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 121.2(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
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 C13 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C13 C8 H8 119.4 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 117.9(3) . . ?
C12 C13 C14 119.7(3) . . ?
C8 C13 C14 122.3(3) . . ?
N1 C14 C13 114.2(2) . . ?
N1 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
N1 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
O3 C15 N1 121.7(3) . . ?
O3 C15 C16 120.7(3) . . ?
N1 C15 C16 117.6(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 S2 119.7(3) . . ?
C15 C16 S2 119.7(2) . . ?
C16 C17 C18 126.1(4) . . ?
C16 C17 H17 116.9 . . ?
C18 C17 H17 116.9 . . ?
C26 C18 C17 117.7(6) . . ?
C26 C18 H18A 107.9 . . ?
C17 C18 H18A 107.9 . . ?
C26 C18 H18B 107.9 . . ?
C17 C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
C20 C19 C24 118.2(3) . . ?
C20 C19 S2 123.4(3) . . ?
C24 C19 S2 118.3(3) . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.9(4) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 117.4(4) . . ?
C23 C22 C25 121.1(4) . . ?
C21 C22 C25 121.5(4) . . ?
C22 C23 C24 121.8(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C18 114.0(11) . . ?
C27 C26 H26A 108.8 . . ?
C18 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C18 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C15 N1 C14 122.4(2) . . ?
C15 N1 S1 117.5(2) . . ?
C14 N1 S1 118.96(19) . . ?
O2 S1 O1 118.52(16) . . ?
O2 S1 N1 109.56(13) . . ?
O1 S1 N1 103.70(13) . . ?
O2 S1 C1 109.28(15) . . ?
O1 S1 C1 108.66(14) . . ?
N1 S1 C1 106.41(13) . . ?
C19 S2 C16 104.57(16) . . ?

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
C6 C1 C2 C3 -0.4(5) . . . . ?
S1 C1 C2 C3 173.7(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C7 -179.4(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C7 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
S1 C1 C6 C5 -173.4(2) . . . . ?
C13 C8 C9 C10 0.7(6) . . . . ?
C8 C9 C10 C11 -1.2(7) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C11 C12 C13 C8 -1.7(5) . . . . ?
C11 C12 C13 C14 175.5(3) . . . . ?
C9 C8 C13 C12 0.7(5) . . . . ?
C9 C8 C13 C14 -176.3(3) . . . . ?
C12 C13 C14 N1 137.4(3) . . . . ?
C8 C13 C14 N1 -45.6(4) . . . . ?
O3 C15 C16 C17 -65.8(5) . . . . ?
N1 C15 C16 C17 115.7(4) . . . . ?
O3 C15 C16 S2 115.7(3) . . . . ?
N1 C15 C16 S2 -62.8(4) . . . . ?
C15 C16 C17 C18 -7.1(7) . . . . ?
S2 C16 C17 C18 171.4(4) . . . . ?
C16 C17 C18 C26 -151.3(7) . . . . ?
C24 C19 C20 C21 0.3(5) . . . . ?
S2 C19 C20 C21 -174.7(3) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C20 C21 C22 C23 -1.1(6) . . . . ?
C20 C21 C22 C25 179.6(4) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C25 C22 C23 C24 179.6(4) . . . . ?
C22 C23 C24 C19 0.7(6) . . . . ?
C20 C19 C24 C23 -1.0(5) . . . . ?
S2 C19 C24 C23 174.2(3) . . . . ?
C17 C18 C26 C27 -73.5(12) . . . . ?
O3 C15 N1 C14 167.9(3) . . . . ?
C16 C15 N1 C14 -13.6(4) . . . . ?
O3 C15 N1 S1 0.5(4) . . . . ?
C16 C15 N1 S1 179.0(2) . . . . ?
C13 C14 N1 C15 -72.0(3) . . . . ?
C13 C14 N1 S1 95.2(3) . . . . ?
C15 N1 S1 O2 57.6(3) . . . . ?
C14 N1 S1 O2 -110.3(2) . . . . ?
C15 N1 S1 O1 -175.0(2) . . . . ?
C14 N1 S1 O1 17.2(2) . . . . ?
C15 N1 S1 C1 -60.4(2) . . . . ?
C14 N1 S1 C1 131.7(2) . . . . ?
C2 C1 S1 O2 -13.9(3) . . . . ?
C6 C1 S1 O2 160.3(2) . . . . ?
C2 C1 S1 O1 -144.6(3) . . . . ?
C6 C1 S1 O1 29.6(3) . . . . ?
C2 C1 S1 N1 104.3(3) . . . . ?
C6 C1 S1 N1 -81.5(3) . . . . ?
C20 C19 S2 C16 -51.8(3) . . . . ?
C24 C19 S2 C16 133.3(3) . . . . ?
C17 C16 S2 C19 150.4(3) . . . . ?
C15 C16 S2 C19 -31.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.044
