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

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_mo_dm14193_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O5 S'
_chemical_formula_weight         347.37

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.7645(9)
_cell_length_b                   7.4690(7)
_cell_length_c                   11.4907(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.351(2)
_cell_angle_gamma                90
_cell_volume                     834.38(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4438
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      30.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8491
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5018
_reflns_number_gt                4718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5018
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93122(4) 0.55236(6) 0.47860(4) 0.02381(11) Uani 1 1 d . . . . .
N1 N 0.67831(17) 0.6320(2) 0.52863(14) 0.0241(3) Uani 1 1 d . . . . .
O1 O 1.19828(18) 0.4893(3) 0.38461(18) 0.0521(5) Uani 1 1 d . . . . .
O2 O 1.13469(15) 0.5943(2) 0.20552(13) 0.0346(4) Uani 1 1 d . . . . .
O3 O 0.83261(14) 0.78515(19) 0.08683(11) 0.0261(3) Uani 1 1 d . . . . .
O4 O 1.00509(16) 0.9412(2) 0.18278(12) 0.0308(3) Uani 1 1 d . . . . .
O5 O 0.52674(14) 0.7410(2) 0.27902(13) 0.0286(3) Uani 1 1 d . . . . .
C1 C 0.98621(19) 0.6358(2) 0.35048(15) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.88764(17) 0.7398(2) 0.29152(14) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.76227(17) 0.7493(2) 0.34480(15) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.77048(18) 0.6510(2) 0.44974(15) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.7164(2) 0.5242(4) 0.63159(19) 0.0365(5) Uani 1 1 d . . . . .
H5A H 0.7488 0.4068 0.6077 0.055 Uiso 1 1 calc R U . . .
H5B H 0.6362 0.5085 0.6759 0.055 Uiso 1 1 calc R U . . .
H5C H 0.7899 0.5844 0.6807 0.055 Uiso 1 1 calc R U . . .
C6 C 0.55988(19) 0.7493(3) 0.53123(18) 0.0287(4) Uani 1 1 d . . . . .
H6A H 0.5825 0.8681 0.5023 0.043 Uiso 1 1 calc R U . . .
H6B H 0.5351 0.7595 0.6117 0.043 Uiso 1 1 calc R U . . .
H6C H 0.4822 0.6994 0.4815 0.043 Uiso 1 1 calc R U . . .
C7 C 0.63474(18) 0.8259(2) 0.28511(15) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.63838(18) 1.0079(2) 0.23263(15) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.7370(2) 1.1336(2) 0.27193(17) 0.0252(4) Uani 1 1 d . . . . .
H9 H 0.8063 1.1034 0.3323 0.030 Uiso 1 1 calc R U . . .
C10 C 0.7340(3) 1.3043(3) 0.2223(2) 0.0329(4) Uani 1 1 d . . . . .
H10 H 0.8024 1.3897 0.2480 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6317(3) 1.3497(3) 0.1359(2) 0.0351(5) Uani 1 1 d . . . . .
H11 H 0.6297 1.4663 0.1028 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5319(2) 1.2252(3) 0.09731(17) 0.0309(4) Uani 1 1 d . . . . .
H12 H 0.4618 1.2564 0.0379 0.037 Uiso 1 1 calc R U . . .
C13 C 0.53497(18) 1.0555(3) 0.14575(15) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.4663 0.9707 0.1198 0.028 Uiso 1 1 calc R U . . .
C14 C 0.90390(18) 0.8218(2) 0.17479(15) 0.0206(3) Uani 1 1 d . . . . .
C15 C 1.0337(3) 1.0271(4) 0.0754(2) 0.0490(7) Uani 1 1 d . . . . .
H15A H 1.0544 0.9360 0.0182 0.074 Uiso 1 1 calc R U . . .
H15B H 1.1129 1.1072 0.0904 0.074 Uiso 1 1 calc R U . . .
H15C H 0.9533 1.0966 0.0445 0.074 Uiso 1 1 calc R U . . .
C16 C 1.11709(18) 0.5666(3) 0.31728(17) 0.0255(3) Uani 1 1 d . . . . .
C17 C 1.2617(2) 0.5253(4) 0.1668(2) 0.0414(6) Uani 1 1 d . . . . .
H17A H 1.3402 0.5803 0.2128 0.062 Uiso 1 1 calc R U . . .
H17B H 1.2657 0.5539 0.0839 0.062 Uiso 1 1 calc R U . . .
H17C H 1.2650 0.3951 0.1774 0.062 Uiso 1 1 calc R U . . .


_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 C1 1.7296(18) . ?
S1 C4 1.7377(18) . ?
N1 C4 1.343(2) . ?
N1 C5 1.451(3) . ?
N1 C6 1.453(3) . ?
O1 C16 1.203(3) . ?
O2 C16 1.328(2) . ?
O2 C17 1.451(2) . ?
O3 C14 1.204(2) . ?
O4 C14 1.328(2) . ?
O4 C15 1.441(2) . ?
O5 C7 1.227(2) . ?
C1 C2 1.367(2) . ?
C1 C16 1.462(2) . ?
C2 C3 1.421(2) . ?
C2 C14 1.496(2) . ?
C3 C4 1.408(2) . ?
C3 C7 1.479(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.489(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.398(2) . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 C4 91.79(9) . . ?
C4 N1 C5 118.18(17) . . ?
C4 N1 C6 122.32(16) . . ?
C5 N1 C6 117.50(17) . . ?
C16 O2 C17 115.65(18) . . ?
C14 O4 C15 116.25(16) . . ?
C2 C1 C16 131.62(16) . . ?
C2 C1 S1 111.51(13) . . ?
C16 C1 S1 116.30(14) . . ?
C1 C2 C3 114.21(15) . . ?
C1 C2 C14 123.25(16) . . ?
C3 C2 C14 122.26(15) . . ?
C4 C3 C2 111.14(15) . . ?
C4 C3 C7 125.24(16) . . ?
C2 C3 C7 122.77(15) . . ?
N1 C4 C3 130.17(17) . . ?
N1 C4 S1 118.45(13) . . ?
C3 C4 S1 111.29(13) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 C3 120.56(16) . . ?
O5 C7 C8 120.11(16) . . ?
C3 C7 C8 119.32(15) . . ?
C9 C8 C13 119.54(17) . . ?
C9 C8 C7 121.81(16) . . ?
C13 C8 C7 118.56(17) . . ?
C8 C9 C10 119.77(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.80(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.46(19) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O3 C14 O4 125.37(17) . . ?
O3 C14 C2 123.94(17) . . ?
O4 C14 C2 110.68(15) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 O2 124.06(19) . . ?
O1 C16 C1 122.81(19) . . ?
O2 C16 C1 113.11(16) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 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
C4 S1 C1 C2 2.36(14) . . . . ?
C4 S1 C1 C16 -169.97(15) . . . . ?
C16 C1 C2 C3 168.09(19) . . . . ?
S1 C1 C2 C3 -2.71(19) . . . . ?
C16 C1 C2 C14 -5.9(3) . . . . ?
S1 C1 C2 C14 -176.68(13) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C14 C2 C3 C4 175.65(15) . . . . ?
C1 C2 C3 C7 -168.35(16) . . . . ?
C14 C2 C3 C7 5.7(2) . . . . ?
C5 N1 C4 C3 -178.6(2) . . . . ?
C6 N1 C4 C3 -15.1(3) . . . . ?
C5 N1 C4 S1 -2.3(2) . . . . ?
C6 N1 C4 S1 161.18(14) . . . . ?
C2 C3 C4 N1 176.68(18) . . . . ?
C7 C3 C4 N1 -13.7(3) . . . . ?
C2 C3 C4 S1 0.21(18) . . . . ?
C7 C3 C4 S1 169.88(13) . . . . ?
C1 S1 C4 N1 -178.37(15) . . . . ?
C1 S1 C4 C3 -1.44(14) . . . . ?
C4 C3 C7 O5 -40.6(3) . . . . ?
C2 C3 C7 O5 127.93(19) . . . . ?
C4 C3 C7 C8 139.17(17) . . . . ?
C2 C3 C7 C8 -52.3(2) . . . . ?
O5 C7 C8 C9 155.53(18) . . . . ?
C3 C7 C8 C9 -24.2(3) . . . . ?
O5 C7 C8 C13 -21.1(2) . . . . ?
C3 C7 C8 C13 159.18(16) . . . . ?
C13 C8 C9 C10 -1.6(3) . . . . ?
C7 C8 C9 C10 -178.16(18) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 1.3(3) . . . . ?
C7 C8 C13 C12 177.92(17) . . . . ?
C15 O4 C14 O3 -2.6(3) . . . . ?
C15 O4 C14 C2 178.6(2) . . . . ?
C1 C2 C14 O3 116.2(2) . . . . ?
C3 C2 C14 O3 -57.3(2) . . . . ?
C1 C2 C14 O4 -65.0(2) . . . . ?
C3 C2 C14 O4 121.54(18) . . . . ?
C17 O2 C16 O1 -0.3(3) . . . . ?
C17 O2 C16 C1 -178.83(19) . . . . ?
C2 C1 C16 O1 173.0(2) . . . . ?
S1 C1 C16 O1 -16.5(3) . . . . ?
C2 C1 C16 O2 -8.5(3) . . . . ?
S1 C1 C16 O2 161.97(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5B O5 0.98 2.64 3.409(3) 135.9 2_646
C5 H5C O4 0.98 2.65 3.354(3) 128.9 2_746
C6 H6A O1 0.98 2.56 3.049(3) 110.6 2_756
C15 H15B O3 0.98 2.53 3.057(3) 113.6 2_755
C17 H17A O5 0.98 2.25 3.215(3) 166.5 1_655

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 998117'
