# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.38

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.4749(2)
_cell_length_b                   16.5165(5)
_cell_length_c                   25.1847(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3109.28(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9017
_exptl_absorpt_correction_T_max  0.9329
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33522
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2737
_reflns_number_gt                2525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0505P)²+1.3402P] 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         2737
_refine_ls_number_parameters     199
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.5739(2) 0.19550(9) 0.46369(5) 0.0462(4) Uani 1 1 d . . .
S1 S 0.28233(5) 0.14297(2) 0.334916(15) 0.03884(15) Uani 1 1 d . . .
O1 O 0.47437(18) 0.30933(7) 0.42099(5) 0.0547(3) Uani 1 1 d . . .
O2 O 0.16434(18) 0.16972(8) 0.29319(5) 0.0556(3) Uani 1 1 d . . .
O3 O 0.22376(17) 0.14983(9) 0.38879(5) 0.0576(4) Uani 1 1 d . . .
C1 C 0.2918(2) -0.01825(12) 0.35784(7) 0.0510(5) Uani 1 1 d . . .
H1A H 0.2414 -0.0047 0.3904 0.061 Uiso 1 1 calc R . .
C2 C 0.3253(3) -0.09850(12) 0.34456(10) 0.0654(6) Uani 1 1 d U . .
H2B H 0.2970 -0.1393 0.3686 0.079 Uiso 1 1 calc R . .
C3 C 0.3994(3) -0.11837(11) 0.29657(10) 0.0613(5) Uani 1 1 d U . .
H3B H 0.4201 -0.1724 0.2882 0.074 Uiso 1 1 calc R . .
C4 C 0.4433(2) -0.05900(11) 0.26080(8) 0.0545(5) Uani 1 1 d . . .
H4A H 0.4950 -0.0728 0.2285 0.065 Uiso 1 1 calc R . .
C5 C 0.4107(2) 0.02110(10) 0.27277(7) 0.0428(4) Uani 1 1 d . . .
H5A H 0.4391 0.0615 0.2485 0.051 Uiso 1 1 calc R . .
C6 C 0.3355(2) 0.04084(9) 0.32121(6) 0.0359(3) Uani 1 1 d . . .
C7 C 0.4825(2) 0.19940(9) 0.32637(6) 0.0384(4) Uani 1 1 d . . .
H7A H 0.5419 0.1793 0.2947 0.046 Uiso 1 1 calc R . .
H7B H 0.4495 0.2552 0.3195 0.046 Uiso 1 1 calc R . .
C8 C 0.6188(2) 0.19914(9) 0.37151(6) 0.0360(3) Uani 1 1 d . . .
C9 C 0.5431(2) 0.24262(10) 0.42075(6) 0.0394(4) Uani 1 1 d . . .
C10 C 0.6506(2) 0.12128(11) 0.44910(7) 0.0455(4) Uani 1 1 d . . .
C11 C 0.6752(2) 0.11874(10) 0.39448(6) 0.0386(4) Uani 1 1 d . . .
C12 C 0.7535(3) 0.05177(11) 0.37163(8) 0.0529(5) Uani 1 1 d . . .
H12A H 0.7713 0.0493 0.3351 0.064 Uiso 1 1 calc R . .
C13 C 0.8055(3) -0.01203(13) 0.40408(11) 0.0694(6) Uani 1 1 d . . .
H13A H 0.8574 -0.0578 0.3891 0.083 Uiso 1 1 calc R . .
C14 C 0.7811(4) -0.00839(15) 0.45788(12) 0.0791(7) Uani 1 1 d . . .
H14A H 0.8176 -0.0516 0.4789 0.095 Uiso 1 1 calc R . .
C15 C 0.7029(3) 0.05864(14) 0.48158(9) 0.0715(6) Uani 1 1 d . . .
H15A H 0.6865 0.0612 0.5181 0.086 Uiso 1 1 calc R . .
C16 C 0.5256(3) 0.21836(15) 0.51766(7) 0.0707(6) Uani 1 1 d . . .
H16A H 0.4765 0.2721 0.5176 0.106 Uiso 1 1 calc R . .
H16B H 0.6302 0.2170 0.5398 0.106 Uiso 1 1 calc R . .
H16C H 0.4383 0.1811 0.5312 0.106 Uiso 1 1 calc R . .
C17 C 0.7818(2) 0.24762(12) 0.35198(8) 0.0522(5) Uani 1 1 d . . .
H17A H 0.8317 0.2217 0.3213 0.078 Uiso 1 1 calc R . .
H17B H 0.8702 0.2498 0.3796 0.078 Uiso 1 1 calc R . .
H17C H 0.7452 0.3016 0.3429 0.078 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
N1 C9 1.352(2) . ?
N1 C10 1.402(2) . ?
N1 C16 1.456(2) . ?
S1 O3 1.4302(13) . ?
S1 O2 1.4412(13) . ?
S1 C6 1.7670(16) . ?
S1 C7 1.7762(16) . ?
O1 C9 1.216(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.390(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2B 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9300 . ?
C7 C8 1.526(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.508(2) . ?
C8 C17 1.539(2) . ?
C8 C9 1.541(2) . ?
C10 C15 1.376(3) . ?
C10 C11 1.388(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.389(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.387(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C9 N1 C10 111.29(13) . . ?
C9 N1 C16 123.73(16) . . ?
C10 N1 C16 124.93(16) . . ?
O3 S1 O2 118.69(9) . . ?
O3 S1 C6 109.26(8) . . ?
O2 S1 C6 106.72(7) . . ?
O3 S1 C7 109.35(8) . . ?
O2 S1 C7 105.46(8) . . ?
C6 S1 C7 106.73(7) . . ?
C6 C1 C2 118.05(18) . . ?
C6 C1 H1A 121.0 . . ?
C2 C1 H1A 121.0 . . ?
C3 C2 C1 120.92(18) . . ?
C3 C2 H2B 119.5 . . ?
C1 C2 H2B 119.5 . . ?
C2 C3 C4 120.34(18) . . ?
C2 C3 H3B 119.8 . . ?
C4 C3 H3B 119.8 . . ?
C3 C4 C5 120.02(18) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 119.42(16) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 121.24(16) . . ?
C1 C6 S1 119.38(13) . . ?
C5 C6 S1 119.28(12) . . ?
C8 C7 S1 118.07(11) . . ?
C8 C7 H7A 107.8 . . ?
S1 C7 H7A 107.8 . . ?
C8 C7 H7B 107.8 . . ?
S1 C7 H7B 107.8 . . ?
H7A C7 H7B 107.1 . . ?
C11 C8 C7 118.33(13) . . ?
C11 C8 C17 111.07(14) . . ?
C7 C8 C17 106.79(13) . . ?
C11 C8 C9 101.78(12) . . ?
C7 C8 C9 110.68(13) . . ?
C17 C8 C9 107.78(13) . . ?
O1 C9 N1 126.13(15) . . ?
O1 C9 C8 125.56(15) . . ?
N1 C9 C8 108.24(14) . . ?
C15 C10 C11 121.91(18) . . ?
C15 C10 N1 128.17(18) . . ?
C11 C10 N1 109.89(15) . . ?
C12 C11 C10 119.64(17) . . ?
C12 C11 C8 131.71(16) . . ?
C10 C11 C8 108.44(14) . . ?
C11 C12 C13 118.8(2) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 121.2(2) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C10 C15 C14 117.7(2) . . ?
C10 C15 H15A 121.2 . . ?
C14 C15 H15A 121.2 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 S1 176.14(14) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 S1 -176.47(13) . . . . ?
O3 S1 C6 C1 9.48(16) . . . . ?
O2 S1 C6 C1 -120.00(14) . . . . ?
C7 S1 C6 C1 127.61(13) . . . . ?
O3 S1 C6 C5 -174.16(13) . . . . ?
O2 S1 C6 C5 56.36(15) . . . . ?
C7 S1 C6 C5 -56.03(14) . . . . ?
O3 S1 C7 C8 37.79(14) . . . . ?
O2 S1 C7 C8 166.47(12) . . . . ?
C6 S1 C7 C8 -80.28(13) . . . . ?
S1 C7 C8 C11 50.28(18) . . . . ?
S1 C7 C8 C17 176.39(12) . . . . ?
S1 C7 C8 C9 -66.56(16) . . . . ?
C10 N1 C9 O1 178.31(16) . . . . ?
C16 N1 C9 O1 0.8(3) . . . . ?
C10 N1 C9 C8 -4.48(19) . . . . ?
C16 N1 C9 C8 177.99(17) . . . . ?
C11 C8 C9 O1 -176.92(16) . . . . ?
C7 C8 C9 O1 -50.3(2) . . . . ?
C17 C8 C9 O1 66.2(2) . . . . ?
C11 C8 C9 N1 5.85(16) . . . . ?
C7 C8 C9 N1 132.50(14) . . . . ?
C17 C8 C9 N1 -111.06(15) . . . . ?
C9 N1 C10 C15 178.9(2) . . . . ?
C16 N1 C10 C15 -3.6(3) . . . . ?
C9 N1 C10 C11 1.0(2) . . . . ?
C16 N1 C10 C11 178.51(17) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
N1 C10 C11 C12 178.30(15) . . . . ?
C15 C10 C11 C8 -175.05(18) . . . . ?
N1 C10 C11 C8 2.99(19) . . . . ?
C7 C8 C11 C12 58.7(2) . . . . ?
C17 C8 C11 C12 -65.3(2) . . . . ?
C9 C8 C11 C12 -179.77(17) . . . . ?
C7 C8 C11 C10 -126.72(15) . . . . ?
C17 C8 C11 C10 109.27(15) . . . . ?
C9 C8 C11 C10 -5.23(16) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C8 C11 C12 C13 174.30(17) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
N1 C10 C15 C14 -178.1(2) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 981556'
