# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1544189'
_audit_update_record             
;
2017-04-15 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O4 S'
_chemical_formula_weight         355.39

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.559(5)
_cell_length_b                   8.777(5)
_cell_length_c                   15.493(5)
_cell_angle_alpha                94.087(5)
_cell_angle_beta                 91.473(5)
_cell_angle_gamma                92.143(5)
_cell_volume                     888.7(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4076
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11725
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             4076
_reflns_number_gt                2674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0521P)²+0.2976P] 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_number_reflns         4076
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_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 0.29223(9) -0.00866(6) 0.24529(4) 0.04933(19) Uani 1 1 d . . . . .
O2 O 0.3939(3) 0.13490(16) 0.27232(12) 0.0647(5) Uani 1 1 d . . . . .
O4 O 0.8403(3) -0.16215(18) 0.49917(11) 0.0626(5) Uani 1 1 d . . . . .
N1 N 0.3849(3) -0.33480(19) 0.39884(11) 0.0436(4) Uani 1 1 d . . . . .
H1 H 0.3674 -0.4235 0.4184 0.052 Uiso 1 1 calc R U . . .
O1 O 0.0781(2) -0.01084(17) 0.22480(12) 0.0614(5) Uani 1 1 d . . . . .
C7 C 0.0964(3) -0.3748(2) 0.29517(13) 0.0387(5) Uani 1 1 d . . . . .
O3 O 0.6986(3) -0.3892(2) 0.52167(12) 0.0756(6) Uani 1 1 d . . . . .
C1 C 0.2653(3) -0.2794(2) 0.33666(13) 0.0398(5) Uani 1 1 d . . . . .
C13 C 0.4161(3) -0.0884(2) 0.15457(15) 0.0491(5) Uani 1 1 d . . . . .
C5 C 0.6955(4) -0.2699(3) 0.48795(14) 0.0505(6) Uani 1 1 d . . . . .
C2 C 0.3450(3) -0.1317(2) 0.32555(14) 0.0435(5) Uani 1 1 d . . . . .
C12 C 0.1204(3) -0.5301(2) 0.27657(14) 0.0473(5) Uani 1 1 d . . . . .
H12 H 0.2451 -0.5723 0.2885 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6148(4) -0.0408(3) 0.13998(18) 0.0620(7) Uani 1 1 d . . . . .
H14 H 0.6805 0.0352 0.1766 0.074 Uiso 1 1 calc R U . . .
C18 C 0.3187(4) -0.2006(3) 0.10005(17) 0.0618(7) Uani 1 1 d . . . . .
H18 H 0.1849 -0.2325 0.1095 0.074 Uiso 1 1 calc R U . . .
C9 C -0.2484(4) -0.4075(3) 0.23940(17) 0.0600(6) Uani 1 1 d . . . . .
H9 H -0.3727 -0.3658 0.2263 0.072 Uiso 1 1 calc R U . . .
C8 C -0.0911(3) -0.3146(2) 0.27558(16) 0.0517(6) Uani 1 1 d . . . . .
H8 H -0.1101 -0.2107 0.2871 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5376(3) -0.2304(2) 0.42634(14) 0.0456(5) Uani 1 1 d . . . . .
C6 C 1.0119(4) -0.1926(3) 0.55531(18) 0.0757(8) Uani 1 1 d . . . . .
H6A H 1.1075 -0.1068 0.5587 0.114 Uiso 1 1 calc R U . . .
H6B H 0.9643 -0.2092 0.6121 0.114 Uiso 1 1 calc R U . . .
H6C H 1.0774 -0.2821 0.5323 0.114 Uiso 1 1 calc R U . . .
C3 C 0.5149(3) -0.1035(2) 0.38171(14) 0.0478(5) Uani 1 1 d . . . . .
H3 H 0.5972 -0.0145 0.3875 0.057 Uiso 1 1 calc R U . . .
C11 C -0.0392(4) -0.6225(3) 0.24061(15) 0.0565(6) Uani 1 1 d . . . . .
H11 H -0.0216 -0.7264 0.2287 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6216(5) -0.2203(4) 0.01568(18) 0.0728(8) Uani 1 1 d . . . . .
C10 C -0.2242(4) -0.5615(3) 0.22240(17) 0.0604(6) Uani 1 1 d . . . . .
H10 H -0.3321 -0.6240 0.1988 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4225(5) -0.2650(3) 0.03125(18) 0.0765(8) Uani 1 1 d . . . . .
H17 H 0.3568 -0.3406 -0.0057 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7140(4) -0.1067(3) 0.0710(2) 0.0743(8) Uani 1 1 d . . . . .
H15 H 0.8473 -0.0740 0.0611 0.089 Uiso 1 1 calc R U . . .
C19 C 0.7355(6) -0.2929(4) -0.0585(2) 0.1100(13) Uani 1 1 d . . . . .
H19A H 0.6484 -0.3691 -0.0900 0.165 Uiso 1 1 calc R U . . .
H19B H 0.7765 -0.2161 -0.0964 0.165 Uiso 1 1 calc R U . . .
H19C H 0.8541 -0.3398 -0.0366 0.165 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 O1 1.4310(19) . ?
S1 O2 1.4337(17) . ?
S1 C2 1.740(2) . ?
S1 C13 1.757(3) . ?
O4 C5 1.314(3) . ?
O4 C6 1.449(3) . ?
N1 C1 1.355(3) . ?
N1 C4 1.370(3) . ?
C7 C12 1.389(3) . ?
C7 C8 1.392(3) . ?
C7 C1 1.469(3) . ?
O3 C5 1.204(3) . ?
C1 C2 1.404(3) . ?
C13 C18 1.378(3) . ?
C13 C14 1.383(3) . ?
C5 C4 1.458(3) . ?
C2 C3 1.400(3) . ?
C12 C11 1.381(3) . ?
C14 C15 1.370(4) . ?
C18 C17 1.378(4) . ?
C9 C8 1.373(3) . ?
C9 C10 1.374(3) . ?
C4 C3 1.363(3) . ?
C11 C10 1.375(3) . ?
C16 C15 1.378(4) . ?
C16 C17 1.382(4) . ?
C16 C19 1.504(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
O1 S1 O2 118.46(10) . . ?
O1 S1 C2 110.99(10) . . ?
O2 S1 C2 106.35(11) . . ?
O1 S1 C13 108.06(11) . . ?
O2 S1 C13 108.20(11) . . ?
C2 S1 C13 103.79(10) . . ?
C5 O4 C6 116.69(18) . . ?
C1 N1 C4 110.83(17) . . ?
C12 C7 C8 118.38(19) . . ?
C12 C7 C1 119.84(18) . . ?
C8 C7 C1 121.76(18) . . ?
N1 C1 C2 105.82(18) . . ?
N1 C1 C7 120.20(17) . . ?
C2 C1 C7 133.95(18) . . ?
C18 C13 C14 120.3(3) . . ?
C18 C13 S1 120.4(2) . . ?
C14 C13 S1 119.28(19) . . ?
O3 C5 O4 123.7(2) . . ?
O3 C5 C4 124.5(2) . . ?
O4 C5 C4 111.73(19) . . ?
C3 C2 C1 108.11(18) . . ?
C3 C2 S1 120.72(16) . . ?
C1 C2 S1 130.04(17) . . ?
C11 C12 C7 120.6(2) . . ?
C15 C14 C13 119.3(3) . . ?
C13 C18 C17 119.1(3) . . ?
C8 C9 C10 120.8(2) . . ?
C9 C8 C7 120.4(2) . . ?
C3 C4 N1 107.81(18) . . ?
C3 C4 C5 131.5(2) . . ?
N1 C4 C5 120.55(19) . . ?
C4 C3 C2 107.41(18) . . ?
C10 C11 C12 120.3(2) . . ?
C15 C16 C17 117.8(3) . . ?
C15 C16 C19 120.7(3) . . ?
C17 C16 C19 121.5(3) . . ?
C9 C10 C11 119.5(2) . . ?
C18 C17 C16 121.7(3) . . ?
C14 C15 C16 121.8(3) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.044

