# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxs
_database_code_depnum_ccdc_archive 'CCDC 1573942'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O6 S'
_chemical_formula_weight         466.49

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                   12.800(3)
_cell_length_b                   7.0766(13)
_cell_length_c                   13.621(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.294(3)
_cell_angle_gamma                90
_cell_volume                     1106.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  
;
Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            8990
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4985
_reflns_number_gt                3799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.991

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0263P)²] 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 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration R,R
_refine_ls_number_reflns         4985
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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_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 0.59358(5) 0.14165(8) 0.27627(5) 0.02066(14) Uani 1 1 d . . . . .
O1 O 1.13127(12) 0.1529(3) 0.71815(12) 0.0255(4) Uani 1 1 d . . . . .
O4 O 0.43265(16) 0.9687(3) 0.02886(14) 0.0345(5) Uani 1 1 d . . . . .
O6 O 0.51343(14) 0.3273(2) 0.42684(13) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.5274(2) 0.3538(3) 0.20926(19) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.50472(13) 0.0156(2) 0.27130(13) 0.0247(4) Uani 1 1 d . . . . .
C14 C 0.5984(2) 0.5025(4) 0.20934(19) 0.0210(5) Uani 1 1 d . . . . .
H14 H 0.6808 0.4916 0.2463 0.025 Uiso 1 1 calc R U . . .
C7 C 0.87863(19) 0.0966(3) 0.45408(19) 0.0210(5) Uani 1 1 d . . . . .
H7 H 0.8605 0.0401 0.3851 0.025 Uiso 1 1 calc R U . . .
O2 O 0.67695(13) 0.0826(2) 0.23933(13) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.93172(19) 0.2582(3) 0.65978(18) 0.0191(5) Uani 1 1 d . . . . .
H4 H 0.9494 0.3115 0.7294 0.023 Uiso 1 1 calc R U . . .
N2 N 0.3718(2) 0.8520(3) 0.04452(16) 0.0273(5) Uani 1 1 d . . . . .
C12 C 0.4262(2) 0.6752(3) 0.10179(18) 0.0224(6) Uani 1 1 d . . . . .
C3 C 0.81944(19) 0.2673(3) 0.57534(19) 0.0179(5) Uani 1 1 d . . . . .
N1 N 0.67093(15) 0.2079(3) 0.40612(15) 0.0190(4) Uani 1 1 d . . . . .
O5 O 0.26813(17) 0.8743(3) 0.01742(18) 0.0490(6) Uani 1 1 d . . . . .
C1 C 0.6166(2) 0.2953(3) 0.46504(19) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.79394(18) 0.1886(3) 0.47401(18) 0.0181(5) Uani 1 1 d . . . . .
C16 C 0.6997(2) 0.6720(4) 0.49691(19) 0.0280(6) Uani 1 1 d . . . . .
H16A H 0.7078 0.8073 0.5140 0.042 Uiso 1 1 calc R U . . .
H16B H 0.6238 0.6481 0.4348 0.042 Uiso 1 1 calc R U . . .
H16C H 0.7618 0.6317 0.4781 0.042 Uiso 1 1 calc R U . . .
C17 C 0.81052(19) 0.6239(4) 0.70170(18) 0.0221(5) Uani 1 1 d . . . . .
C24 C 0.6830(2) 0.2261(4) 0.6608(2) 0.0247(6) Uani 1 1 d . . . . .
H24A H 0.6102 0.2715 0.6597 0.037 Uiso 1 1 calc R U . . .
H24B H 0.7467 0.2405 0.7347 0.037 Uiso 1 1 calc R U . . .
H24C H 0.6748 0.0925 0.6398 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3552(2) 0.5289(4) 0.1008(2) 0.0321(6) Uani 1 1 d . . . . .
H11 H 0.2728 0.5401 0.0635 0.039 Uiso 1 1 calc R U . . .
C22 C 0.9100(2) 0.7071(4) 0.7040(2) 0.0267(6) Uani 1 1 d . . . . .
H22 H 0.9137 0.7310 0.6370 0.032 Uiso 1 1 calc R U . . .
C5 C 1.01738(18) 0.1702(3) 0.64060(18) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.71051(19) 0.3422(3) 0.57918(19) 0.0186(5) Uani 1 1 d . . . . .
C13 C 0.54625(19) 0.6664(4) 0.15447(17) 0.0218(5) Uani 1 1 d . . . . .
H13 H 0.5921 0.7709 0.1530 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9909(2) 0.0905(3) 0.53900(19) 0.0220(5) Uani 1 1 d . . . . .
H6 H 1.0508 0.0304 0.5274 0.026 Uiso 1 1 calc R U . . .
C23 C 1.1591(2) 0.2332(4) 0.82289(19) 0.0301(6) Uani 1 1 d . . . . .
H23A H 1.1490 0.3706 0.8158 0.045 Uiso 1 1 calc R U . . .
H23B H 1.2402 0.2037 0.8733 0.045 Uiso 1 1 calc R U . . .
H23C H 1.1073 0.1806 0.8515 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4075(2) 0.3641(4) 0.1560(2) 0.0313(6) Uani 1 1 d . . . . .
H10 H 0.3613 0.2598 0.1570 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7084(2) 0.5614(3) 0.59613(19) 0.0201(5) Uani 1 1 d . . . . .
H15 H 0.6361 0.5894 0.6042 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8077(2) 0.5949(4) 0.8022(2) 0.0300(6) Uani 1 1 d . . . . .
H18 H 0.7403 0.5405 0.8033 0.036 Uiso 1 1 calc R U . . .
C21 C 1.0036(2) 0.7558(4) 0.8018(2) 0.0359(7) Uani 1 1 d . . . . .
H21 H 1.0709 0.8117 0.8013 0.043 Uiso 1 1 calc R U . . .
C19 C 0.9008(2) 0.6439(5) 0.8997(2) 0.0369(6) Uani 1 1 d . . . . .
H19 H 0.8969 0.6229 0.9669 0.044 Uiso 1 1 calc R U . . .
C20 C 0.9997(2) 0.7234(4) 0.9004(2) 0.0383(7) Uani 1 1 d . . . . .
H20 H 1.0642 0.7553 0.9677 0.046 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 O3 1.4232(17) . ?
S1 O2 1.4292(16) . ?
S1 N1 1.6663(19) . ?
S1 C9 1.766(2) . ?
O1 C5 1.375(2) . ?
O1 C23 1.426(3) . ?
O4 N2 1.217(3) . ?
O6 C1 1.207(3) . ?
C9 C10 1.378(3) . ?
C9 C14 1.390(3) . ?
C14 C13 1.381(3) . ?
C7 C6 1.390(3) . ?
C7 C8 1.390(3) . ?
C4 C5 1.383(3) . ?
C4 C3 1.389(3) . ?
N2 O5 1.220(3) . ?
N2 C12 1.476(3) . ?
C12 C11 1.374(3) . ?
C12 C13 1.379(3) . ?
C3 C8 1.387(3) . ?
C3 C2 1.514(3) . ?
N1 C1 1.416(3) . ?
N1 C8 1.436(3) . ?
C1 C2 1.522(3) . ?
C16 C15 1.522(3) . ?
C17 C22 1.390(3) . ?
C17 C18 1.401(3) . ?
C17 C15 1.518(3) . ?
C24 C2 1.543(3) . ?
C11 C10 1.388(4) . ?
C22 C21 1.384(3) . ?
C5 C6 1.390(3) . ?
C2 C15 1.570(3) . ?
C18 C19 1.379(3) . ?
C21 C20 1.385(4) . ?
C19 C20 1.382(4) . ?

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
O3 S1 O2 120.37(10) . . ?
O3 S1 N1 108.26(9) . . ?
O2 S1 N1 105.70(9) . . ?
O3 S1 C9 108.52(11) . . ?
O2 S1 C9 109.20(11) . . ?
N1 S1 C9 103.47(11) . . ?
C5 O1 C23 116.29(17) . . ?
C10 C9 C14 122.4(2) . . ?
C10 C9 S1 118.99(19) . . ?
C14 C9 S1 118.62(18) . . ?
C13 C14 C9 118.4(2) . . ?
C6 C7 C8 117.4(2) . . ?
C5 C4 C3 118.7(2) . . ?
O4 N2 O5 123.6(2) . . ?
O4 N2 C12 118.6(2) . . ?
O5 N2 C12 117.7(2) . . ?
C11 C12 C13 123.4(2) . . ?
C11 C12 N2 118.6(2) . . ?
C13 C12 N2 118.0(2) . . ?
C8 C3 C4 120.4(2) . . ?
C8 C3 C2 111.15(19) . . ?
C4 C3 C2 128.2(2) . . ?
C1 N1 C8 110.51(17) . . ?
C1 N1 S1 120.94(15) . . ?
C8 N1 S1 128.55(14) . . ?
O6 C1 N1 123.8(2) . . ?
O6 C1 C2 128.1(2) . . ?
N1 C1 C2 108.06(18) . . ?
C3 C8 C7 121.5(2) . . ?
C3 C8 N1 108.08(18) . . ?
C7 C8 N1 130.2(2) . . ?
C22 C17 C18 117.4(2) . . ?
C22 C17 C15 122.7(2) . . ?
C18 C17 C15 119.9(2) . . ?
C12 C11 C10 118.0(2) . . ?
C21 C22 C17 121.5(2) . . ?
O1 C5 C4 123.7(2) . . ?
O1 C5 C6 115.91(19) . . ?
C4 C5 C6 120.4(2) . . ?
C3 C2 C1 102.19(18) . . ?
C3 C2 C24 110.21(19) . . ?
C1 C2 C24 106.88(19) . . ?
C3 C2 C15 115.27(19) . . ?
C1 C2 C15 107.99(19) . . ?
C24 C2 C15 113.35(19) . . ?
C12 C13 C14 118.6(2) . . ?
C7 C6 C5 121.5(2) . . ?
C9 C10 C11 119.2(2) . . ?
C17 C15 C16 112.7(2) . . ?
C17 C15 C2 111.3(2) . . ?
C16 C15 C2 112.12(19) . . ?
C19 C18 C17 121.3(2) . . ?
C22 C21 C20 120.2(3) . . ?
C18 C19 C20 120.5(3) . . ?
C19 C20 C21 119.2(2) . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-3

