# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_t_a
_audit_block_doi                 10.5517/ccdc.csd.cc1pvqmw
_database_code_depnum_ccdc_archive 'CCDC 1574819'
_audit_update_record             
;
2017-09-16 deposited with the CCDC.
2017-12-12 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         'C22 H20 N2 O2 S'
_chemical_formula_sum            'C22 H20 N2 O2 S'
_chemical_formula_weight         376.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.7907(3)
_cell_length_b                   10.0612(3)
_cell_length_c                   10.7006(3)
_cell_angle_alpha                87.7110(10)
_cell_angle_beta                 85.0380(10)
_cell_angle_gamma                61.8340(10)
_cell_volume                     925.77(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.710
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100 '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18823
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.147
_diffrn_reflns_theta_max         68.307
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3351
_reflns_number_gt                3206
_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)+(0.0473P)²+0.3638P] 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         3351
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.41682(3) 0.68413(3) 0.72309(3) 0.02055(11) Uani 1 1 d . . . . .
C1 C 0.94332(15) 0.30727(15) 0.88529(12) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.70102(13) 0.30354(12) 0.84302(10) 0.0242(2) Uani 1 1 d . . . . .
O1 O 0.51910(11) 0.70216(10) 0.62616(9) 0.0284(2) Uani 1 1 d . . . . .
O2 O 0.36081(11) 0.79223(10) 0.82448(9) 0.0289(2) Uani 1 1 d . . . . .
C2 C 1.10468(16) 0.22598(17) 0.88102(14) 0.0324(3) Uani 1 1 d . . . . .
H2 H 1.1544 0.1202 0.8948 0.039 Uiso 1 1 calc R U . . .
N2 N 0.49343(13) 0.51153(12) 0.77109(11) 0.0251(2) Uani 1 1 d . . . . .
C7 C 0.69667(16) 0.54271(15) 0.87518(14) 0.0296(3) Uani 1 1 d . . . . .
H7A H 0.6602 0.6394 0.8291 0.036 Uiso 1 1 calc R U . . .
H7B H 0.6601 0.5664 0.9647 0.036 Uiso 1 1 calc R U . . .
C6 C 0.87126(15) 0.46109(15) 0.86358(12) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.95951(18) 0.53493(17) 0.83570(13) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.9101 0.6399 0.8183 0.038 Uiso 1 1 calc R U . . .
C4 C 1.12038(18) 0.45411(19) 0.83350(13) 0.0364(4) Uani 1 1 d . . . . .
H4 H 1.1812 0.5044 0.8162 0.044 Uiso 1 1 calc R U . . .
C3 C 1.19242(17) 0.3007(2) 0.85647(14) 0.0375(4) Uani 1 1 d . . . . .
H3 H 1.3025 0.2462 0.8554 0.045 Uiso 1 1 calc R U . . .
C8 C 0.62494(15) 0.45333(14) 0.82490(12) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.84039(16) 0.23557(16) 0.91667(14) 0.0288(3) Uani 1 1 d . . . . .
H9A H 0.8999 0.1261 0.8988 0.035 Uiso 1 1 calc R U . . .
H9B H 0.8069 0.2484 1.0073 0.035 Uiso 1 1 calc R U . . .
C10 C 0.64708(14) 0.20315(14) 0.80168(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.64126(16) 0.09597(15) 0.88466(13) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.6667 0.0931 0.9687 0.032 Uiso 1 1 calc R U . . .
C12 C 0.59780(17) -0.00714(16) 0.84357(14) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.5962 -0.0823 0.8994 0.038 Uiso 1 1 calc R U . . .
C13 C 0.55700(17) -0.00117(16) 0.72219(14) 0.0309(3) Uani 1 1 d . . . . .
H13 H 0.5261 -0.0710 0.6949 0.037 Uiso 1 1 calc R U . . .
C14 C 0.56155(16) 0.10753(15) 0.64043(13) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.5324 0.1127 0.5573 0.033 Uiso 1 1 calc R U . . .
C15 C 0.60819(15) 0.20843(14) 0.67910(12) 0.0246(3) Uani 1 1 d . . . . .
H15 H 0.6136 0.2810 0.6221 0.029 Uiso 1 1 calc R U . . .
C16 C 0.25389(15) 0.70020(14) 0.65256(12) 0.0224(3) Uani 1 1 d . . . . .
C17 C 0.26761(15) 0.59276(15) 0.56814(12) 0.0261(3) Uani 1 1 d . . . . .
H17 H 0.3639 0.5041 0.5528 0.031 Uiso 1 1 calc R U . . .
C18 C 0.13942(16) 0.61615(16) 0.50632(13) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.1490 0.5430 0.4480 0.035 Uiso 1 1 calc R U . . .
C19 C -0.00278(17) 0.74451(17) 0.52795(14) 0.0323(3) Uani 1 1 d . . . . .
C20 C -0.01339(18) 0.85002(18) 0.61321(17) 0.0426(4) Uani 1 1 d . . . . .
H20 H -0.1098 0.9383 0.6293 0.051 Uiso 1 1 calc R U . . .
C21 C 0.11343(17) 0.82943(16) 0.67526(15) 0.0353(3) Uani 1 1 d . . . . .
H21 H 0.1043 0.9032 0.7329 0.042 Uiso 1 1 calc R U . . .
C22 C -0.14274(19) 0.7679(2) 0.46237(17) 0.0469(4) Uani 1 1 d . . . . .
H22A H -0.1875 0.8669 0.4218 0.070 Uiso 1 1 calc R U . . .
H22B H -0.2204 0.7627 0.5238 0.070 Uiso 1 1 calc R U . . .
H22C H -0.1113 0.6891 0.3989 0.070 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 1.4451(9) . ?
S1 O2 1.4452(9) . ?
S1 N2 1.6149(11) . ?
S1 C16 1.7595(13) . ?
C1 C6 1.3840(19) . ?
C1 C2 1.3920(19) . ?
C1 C9 1.5024(19) . ?
N1 C8 1.3438(17) . ?
N1 C10 1.4403(16) . ?
N1 C9 1.4876(16) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
N2 C8 1.3122(17) . ?
C7 C6 1.5027(19) . ?
C7 C8 1.5138(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C5 1.3896(19) . ?
C5 C4 1.389(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.383(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3882(18) . ?
C10 C15 1.3892(19) . ?
C11 C12 1.3915(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3835(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.3857(19) . ?
C16 C17 1.3865(18) . ?
C17 C18 1.3858(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C19 C22 1.508(2) . ?
C20 C21 1.384(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 S1 O2 115.65(6) . . ?
O1 S1 N2 110.06(6) . . ?
O2 S1 N2 113.08(6) . . ?
O1 S1 C16 107.86(6) . . ?
O2 S1 C16 107.60(6) . . ?
N2 S1 C16 101.45(6) . . ?
C6 C1 C2 120.14(13) . . ?
C6 C1 C9 117.26(12) . . ?
C2 C1 C9 122.58(13) . . ?
C8 N1 C10 122.69(10) . . ?
C8 N1 C9 120.33(11) . . ?
C10 N1 C9 116.82(10) . . ?
C3 C2 C1 119.48(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C8 N2 S1 119.96(9) . . ?
C6 C7 C8 113.27(11) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C1 C6 C5 120.25(13) . . ?
C1 C6 C7 117.26(12) . . ?
C5 C6 C7 122.47(13) . . ?
C4 C5 C6 119.53(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C3 C4 C5 120.25(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 120.32(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N2 C8 N1 118.85(11) . . ?
N2 C8 C7 125.13(11) . . ?
N1 C8 C7 115.96(11) . . ?
N1 C9 C1 111.46(11) . . ?
N1 C9 H9A 109.3 . . ?
C1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C15 120.28(12) . . ?
C11 C10 N1 118.93(12) . . ?
C15 C10 N1 120.73(11) . . ?
C10 C11 C12 119.41(13) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.56(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.53(13) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.53(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 119.67(12) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C21 C16 C17 120.42(12) . . ?
C21 C16 S1 118.28(10) . . ?
C17 C16 S1 121.09(10) . . ?
C18 C17 C16 119.30(12) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 121.33(13) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.17(13) . . ?
C20 C19 C22 120.73(14) . . ?
C18 C19 C22 121.09(14) . . ?
C21 C20 C19 121.45(14) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C16 119.34(13) . . ?
C20 C21 H21 120.3 . . ?
C16 C21 H21 120.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 0.8(2) . . . . ?
C9 C1 C2 C3 -177.34(13) . . . . ?
O1 S1 N2 C8 62.73(12) . . . . ?
O2 S1 N2 C8 -68.30(12) . . . . ?
C16 S1 N2 C8 176.76(11) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C9 C1 C6 C5 179.16(12) . . . . ?
C2 C1 C6 C7 -177.42(13) . . . . ?
C9 C1 C6 C7 0.84(18) . . . . ?
C8 C7 C6 C1 -38.34(17) . . . . ?
C8 C7 C6 C5 143.38(13) . . . . ?
C1 C6 C5 C4 -1.9(2) . . . . ?
C7 C6 C5 C4 176.28(13) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
S1 N2 C8 N1 -167.84(10) . . . . ?
S1 N2 C8 C7 15.28(18) . . . . ?
C10 N1 C8 N2 2.32(19) . . . . ?
C9 N1 C8 N2 -172.90(12) . . . . ?
C10 N1 C8 C7 179.48(12) . . . . ?
C9 N1 C8 C7 4.26(18) . . . . ?
C6 C7 C8 N2 -147.25(13) . . . . ?
C6 C7 C8 N1 35.79(17) . . . . ?
C8 N1 C9 C1 -41.37(17) . . . . ?
C10 N1 C9 C1 143.13(12) . . . . ?
C6 C1 C9 N1 37.87(17) . . . . ?
C2 C1 C9 N1 -143.91(13) . . . . ?
C8 N1 C10 C11 -132.22(13) . . . . ?
C9 N1 C10 C11 43.16(17) . . . . ?
C8 N1 C10 C15 50.72(18) . . . . ?
C9 N1 C10 C15 -133.91(13) . . . . ?
C15 C10 C11 C12 0.7(2) . . . . ?
N1 C10 C11 C12 -176.36(12) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 C10 -1.6(2) . . . . ?
C11 C10 C15 C14 0.85(19) . . . . ?
N1 C10 C15 C14 177.88(12) . . . . ?
O1 S1 C16 C21 -107.80(12) . . . . ?
O2 S1 C16 C21 17.61(13) . . . . ?
N2 S1 C16 C21 136.55(12) . . . . ?
O1 S1 C16 C17 66.88(12) . . . . ?
O2 S1 C16 C17 -167.72(10) . . . . ?
N2 S1 C16 C17 -48.78(12) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
S1 C16 C17 C18 -174.37(10) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C22 -178.74(14) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C22 C19 C20 C21 179.22(16) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C17 C16 C21 C20 0.3(2) . . . . ?
S1 C16 C21 C20 174.98(13) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.039

