# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1442520'
_audit_update_record             
;
2015-12-15 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 N O5 S'
_chemical_formula_sum            'C18 H17 N O5 S'
_chemical_melting_point          ?

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(1)
_chemical_formula_weight         359.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2474(5)
_cell_length_b                   11.1326(7)
_cell_length_c                   18.0136(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1653.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      36.85
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9154
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35872
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         36.853
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8255
_reflns_number_gt                7739
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    1.000

_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    ?
_computing_publication_material  ?

_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)+(0.0472P)²+0.1045P] 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 3265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.049(11)
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8255
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.003
_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 0.38095(3) 0.56413(2) 0.80592(2) 0.01607(5) Uani 1 1 d . . . . .
O2 O 0.35449(13) 0.45854(8) 0.76167(5) 0.0287(2) Uani 1 1 d . . . . .
O1 O 0.50622(10) 0.64732(9) 0.78400(5) 0.02394(17) Uani 1 1 d . . . . .
C6 C 0.19654(12) 0.64272(10) 0.81211(6) 0.01623(16) Uani 1 1 d . . . . .
C7 C 0.42844(11) 0.51656(9) 0.89951(5) 0.01406(15) Uani 1 1 d . . . . .
C10 C 0.42221(13) 0.62407(9) 0.95507(6) 0.01700(17) Uani 1 1 d . . . . .
C1 C 0.19823(14) 0.76226(11) 0.83504(7) 0.02084(19) Uani 1 1 d . . . . .
H1 H 0.2953 0.8001 0.8470 0.025 Uiso 1 1 calc R U . . .
C5 C 0.05373(14) 0.58480(11) 0.79249(6) 0.0221(2) Uani 1 1 d . . . . .
H5 H 0.0548 0.5049 0.7773 0.026 Uiso 1 1 calc R U . . .
C8 C 0.28093(13) 0.46255(10) 0.94226(6) 0.01877(18) Uani 1 1 d . . . . .
H8A H 0.1838 0.4558 0.9122 0.023 Uiso 1 1 calc R U . . .
H8B H 0.3050 0.3870 0.9667 0.023 Uiso 1 1 calc R U . . .
C4 C -0.09093(14) 0.64877(14) 0.79598(7) 0.0271(2) Uani 1 1 d . . . . .
H4 H -0.1876 0.6119 0.7822 0.033 Uiso 1 1 calc R U . . .
C2 C 0.05175(17) 0.82395(13) 0.83979(8) 0.0282(2) Uani 1 1 d . . . . .
H2 H 0.0502 0.9031 0.8563 0.034 Uiso 1 1 calc R U . . .
C9 C 0.27857(16) 0.57125(12) 0.99575(7) 0.0263(2) Uani 1 1 d . . . . .
H9A H 0.1810 0.6195 0.9922 0.032 Uiso 1 1 calc R U . . .
H9B H 0.3014 0.5503 1.0470 0.032 Uiso 1 1 calc R U . . .
C3 C -0.09178(16) 0.76764(15) 0.81994(7) 0.0303(3) Uani 1 1 d . . . . .
H3 H -0.1892 0.8095 0.8226 0.036 Uiso 1 1 calc R U . . .
O3 O 0.50365(12) 0.71164(8) 0.96159(5) 0.02556(18) Uani 1 1 d . . . . .
C12 C 0.66796(12) 0.44080(9) 0.97670(5) 0.01462(15) Uani 1 1 d . . . . .
C11 C 0.59446(11) 0.45071(9) 0.89936(5) 0.01471(15) Uani 1 1 d . . . . .
H11 H 0.6691 0.4988 0.8692 0.018 Uiso 1 1 calc R U . . .
C13 C 0.61290(14) 0.35765(10) 1.02894(6) 0.01885(17) Uani 1 1 d . . . . .
H13 H 0.5272 0.3069 1.0171 0.023 Uiso 1 1 calc R U . . .
C17 C 0.79873(13) 0.51485(10) 0.99526(6) 0.01828(17) Uani 1 1 d . . . . .
H17 H 0.8364 0.5709 0.9611 0.022 Uiso 1 1 calc R U . . .
C16 C 0.87304(14) 0.50543(11) 1.06432(6) 0.02136(19) Uani 1 1 d . . . . .
H16 H 0.9612 0.5541 1.0757 0.026 Uiso 1 1 calc R U . . .
C18 C 0.58106(14) 0.32698(10) 0.86270(7) 0.02013(19) Uani 1 1 d . . . . .
H18A H 0.5027 0.2783 0.8893 0.024 Uiso 1 1 calc R U . . .
H18B H 0.5438 0.3359 0.8119 0.024 Uiso 1 1 calc R U . . .
C14 C 0.68518(15) 0.34996(11) 1.09868(6) 0.02184(19) Uani 1 1 d . . . . .
H14 H 0.6459 0.2956 1.1335 0.026 Uiso 1 1 calc R U . . .
C15 C 0.81590(14) 0.42342(11) 1.11631(6) 0.0220(2) Uani 1 1 d . . . . .
H15 H 0.8649 0.4177 1.1627 0.026 Uiso 1 1 calc R U . . .
N1 N 0.74294(13) 0.26603(10) 0.86342(6) 0.02193(18) Uani 1 1 d . . . . .
O5 O 0.86206(13) 0.32528(10) 0.84633(7) 0.0346(2) Uani 1 1 d . . . . .
O4 O 0.74703(16) 0.15959(10) 0.87965(7) 0.0371(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
S1 O2 1.4369(9) . ?
S1 O1 1.4425(9) . ?
S1 C6 1.7581(10) . ?
S1 C7 1.8101(10) . ?
C6 C5 1.3885(15) . ?
C6 C1 1.3935(16) . ?
C7 C11 1.5531(13) . ?
C7 C8 1.5603(14) . ?
C7 C10 1.5610(14) . ?
C10 O3 1.1896(14) . ?
C10 C9 1.5121(17) . ?
C1 C2 1.3923(17) . ?
C5 C4 1.3909(17) . ?
C8 C9 1.5470(18) . ?
C4 C3 1.392(2) . ?
C2 C3 1.386(2) . ?
C12 C13 1.3959(14) . ?
C12 C17 1.3981(14) . ?
C12 C11 1.5233(13) . ?
C11 C18 1.5316(14) . ?
C13 C14 1.3932(16) . ?
C17 C16 1.3906(16) . ?
C16 C15 1.3903(17) . ?
C18 N1 1.4977(15) . ?
C14 C15 1.3899(17) . ?
N1 O4 1.2210(15) . ?
N1 O5 1.2227(16) . ?

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 118.83(6) . . ?
O2 S1 C6 108.11(5) . . ?
O1 S1 C6 108.50(5) . . ?
O2 S1 C7 108.07(5) . . ?
O1 S1 C7 106.72(5) . . ?
C6 S1 C7 105.89(5) . . ?
C5 C6 C1 121.83(10) . . ?
C5 C6 S1 119.12(9) . . ?
C1 C6 S1 119.04(8) . . ?
C11 C7 C8 120.42(8) . . ?
C11 C7 C10 113.08(8) . . ?
C8 C7 C10 87.33(8) . . ?
C11 C7 S1 109.10(6) . . ?
C8 C7 S1 113.81(7) . . ?
C10 C7 S1 111.45(7) . . ?
O3 C10 C9 135.50(11) . . ?
O3 C10 C7 132.30(10) . . ?
C9 C10 C7 92.20(8) . . ?
C2 C1 C6 118.73(11) . . ?
C6 C5 C4 118.58(11) . . ?
C9 C8 C7 90.90(8) . . ?
C5 C4 C3 120.34(11) . . ?
C3 C2 C1 120.13(12) . . ?
C10 C9 C8 89.57(8) . . ?
C2 C3 C4 120.37(11) . . ?
C13 C12 C17 118.73(9) . . ?
C13 C12 C11 122.35(9) . . ?
C17 C12 C11 118.88(9) . . ?
C12 C11 C18 110.97(8) . . ?
C12 C11 C7 112.54(8) . . ?
C18 C11 C7 111.20(8) . . ?
C14 C13 C12 120.63(10) . . ?
C16 C17 C12 120.62(10) . . ?
C15 C16 C17 120.18(11) . . ?
N1 C18 C11 109.84(9) . . ?
C15 C14 C13 120.12(11) . . ?
C14 C15 C16 119.69(10) . . ?
O4 N1 O5 124.17(12) . . ?
O4 N1 C18 117.80(11) . . ?
O5 N1 C18 118.01(10) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

