# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ard_ms_pac3_0m
_database_code_depnum_ccdc_archive 'CCDC 1457208'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N2 O2 S'
_chemical_formula_sum            'C23 H21 N2 O2 S'
_chemical_formula_weight         389.48

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_hall_group_name_H-M    '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9365(7)
_cell_length_b                   10.9597(9)
_cell_length_c                   11.7375(9)
_cell_angle_alpha                100.397(2)
_cell_angle_beta                 92.839(2)
_cell_angle_gamma                105.871(2)
_cell_volume                     1081.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3782
_cell_measurement_theta_min      0.959
_cell_measurement_theta_max      0.985

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12254
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         24.95
_reflns_number_total             3749
_reflns_number_gt                2720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2291
_refine_ls_R_factor_gt           0.1963
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   4.875
_refine_ls_restrained_S_all      4.875
_refine_ls_shift/su_max          0.155
_refine_ls_shift/su_mean         0.010

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.6873(15) 0.1476(15) 0.8766(11) 0.117(4) Uani 1 1 d . . .
H3 H 0.7931 0.1580 0.8946 0.140 Uiso 1 1 calc R . .
O2 O -0.2377(9) -0.1949(6) 0.5960(6) 0.119(3) Uani 1 1 d . . .
N1 N 0.1701(7) 0.1750(6) 0.7041(6) 0.0696(19) Uani 1 1 d . . .
H6 H 0.2253 0.2545 0.7141 0.084 Uiso 1 1 calc R . .
C17 C -0.1121(12) -0.3379(9) 0.9770(8) 0.086(3) Uani 1 1 d . . .
H10 H -0.1608 -0.3792 1.0336 0.103 Uiso 1 1 calc R . .
C16 C -0.0400(12) -0.4025(8) 0.8957(9) 0.095(3) Uani 1 1 d . . .
H9 H -0.0345 -0.4851 0.9000 0.114 Uiso 1 1 calc R . .
C15 C 0.0244(11) -0.3436(7) 0.8076(7) 0.081(3) Uani 1 1 d . . .
H8 H 0.0657 -0.3894 0.7489 0.097 Uiso 1 1 calc R . .
C14 C 0.0275(9) -0.2179(7) 0.8066(6) 0.065(2) Uani 1 1 d . . .
N2 N 0.0999(9) -0.1608(6) 0.7176(6) 0.082(2) Uani 1 1 d . . .
H7 H 0.1467 -0.2035 0.6701 0.098 Uiso 1 1 calc R . .
C8 C 0.0983(11) -0.0366(7) 0.7039(6) 0.069(2) Uani 1 1 d . . .
C9 C -0.0266(10) -0.0025(7) 0.6532(6) 0.070(2) Uani 1 1 d . . .
C10 C 0.0204(9) 0.1276(7) 0.6545(6) 0.065(2) Uani 1 1 d . . .
C11 C -0.0789(9) 0.1949(7) 0.6053(6) 0.064(2) Uani 1 1 d . . .
C20 C -0.0421(10) 0.3263(8) 0.6065(7) 0.071(2) Uani 1 1 d . . .
H16 H 0.0553 0.3809 0.6396 0.085 Uiso 1 1 calc R . .
C21 C -0.1489(11) 0.3750(10) 0.5590(9) 0.093(3) Uani 1 1 d . . .
H15 H -0.1243 0.4633 0.5595 0.111 Uiso 1 1 calc R . .
C22 C -0.2968(12) 0.2928(12) 0.5091(9) 0.098(3) Uani 1 1 d . . .
H14 H -0.3680 0.3274 0.4755 0.118 Uiso 1 1 calc R . .
C18 C -0.1130(12) -0.2136(9) 0.9753(7) 0.083(3) Uani 1 1 d . . .
H11 H -0.1616 -0.1704 1.0307 0.100 Uiso 1 1 calc R . .
C19 C -0.0409(11) -0.1527(8) 0.8906(7) 0.080(3) Uani 1 1 d . . .
H12 H -0.0386 -0.0674 0.8904 0.096 Uiso 1 1 calc R . .
C7 C 0.2212(11) 0.0769(7) 0.7361(6) 0.069(2) Uani 1 1 d . . .
C6 C 0.3830(11) 0.1002(8) 0.7873(7) 0.076(3) Uani 1 1 d . . .
C5 C 0.428(2) 0.0178(13) 0.822(2) 0.275(15) Uani 1 1 d . . .
H5 H 0.3580 -0.0644 0.8132 0.330 Uiso 1 1 calc R . .
C4 C 0.580(3) 0.0382(16) 0.876(2) 0.280(15) Uani 1 1 d . . .
H4 H 0.6044 -0.0250 0.9107 0.336 Uiso 1 1 calc R . .
C2 C 0.6401(17) 0.2341(19) 0.852(2) 0.245(14) Uani 1 1 d . . .
H2 H 0.7043 0.3189 0.8732 0.294 Uiso 1 1 calc R . .
C1 C 0.4868(13) 0.2093(15) 0.791(2) 0.211(10) Uani 1 1 d . . .
H1 H 0.4632 0.2717 0.7553 0.253 Uiso 1 1 calc R . .
C23 C -0.3366(11) 0.1662(11) 0.5089(8) 0.096(3) Uani 1 1 d . . .
H13 H -0.4351 0.1127 0.4769 0.115 Uiso 1 1 calc R . .
C12 C -0.2271(10) 0.1165(9) 0.5579(7) 0.079(2) Uani 1 1 d . . .
C13 C -0.1805(12) -0.0804(9) 0.6015(8) 0.083(3) Uani 1 1 d . . .
O1 O -0.2736(7) -0.0166(6) 0.5554(5) 0.090(2) Uani 1 1 d . . .
S1 S 0.4430(7) 0.5464(5) 0.7835(8) 0.331(7) Uani 1 1 d . . .
O3 O 0.3126(7) 0.4480(6) 0.7623(6) 0.104(2) Uani 1 1 d . . .
C24 C 0.5902(18) 0.5497(18) 0.7070(19) 0.189(7) Uani 1 1 d . . .
H21 H 0.6749 0.5376 0.7530 0.284 Uiso 1 1 calc R . .
H20 H 0.6235 0.6318 0.6838 0.284 Uiso 1 1 calc R . .
H22 H 0.5591 0.4816 0.6389 0.284 Uiso 1 1 calc R . .
C25 C 0.458(2) 0.681(2) 0.845(4) 0.39(3) Uani 1 1 d . . .
H18 H 0.3688 0.7060 0.8212 0.578 Uiso 1 1 calc R . .
H17 H 0.5515 0.7384 0.8272 0.578 Uiso 1 1 calc R . .
H19 H 0.4636 0.6841 0.9279 0.578 Uiso 1 1 calc R . .


_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
C3 C2 1.209(18) . ?
C3 C4 1.31(2) . ?
C3 H3 0.9300 . ?
O2 C13 1.206(10) . ?
N1 C10 1.354(9) . ?
N1 C7 1.379(10) . ?
N1 H6 0.8600 . ?
C17 C18 1.368(12) . ?
C17 C16 1.376(13) . ?
C17 H10 0.9300 . ?
C16 C15 1.383(12) . ?
C16 H9 0.9300 . ?
C15 C14 1.373(10) . ?
C15 H8 0.9300 . ?
C14 C19 1.379(11) . ?
C14 N2 1.409(9) . ?
N2 C8 1.403(10) . ?
N2 H7 0.8600 . ?
C8 C7 1.392(11) . ?
C8 C9 1.408(12) . ?
C9 C10 1.370(10) . ?
C9 C13 1.441(12) . ?
C10 C11 1.457(11) . ?
C11 C20 1.384(10) . ?
C11 C12 1.391(11) . ?
C20 C21 1.356(12) . ?
C20 H16 0.9300 . ?
C21 C22 1.409(13) . ?
C21 H15 0.9300 . ?
C22 C23 1.334(13) . ?
C22 H14 0.9300 . ?
C18 C19 1.384(11) . ?
C18 H11 0.9300 . ?
C19 H12 0.9300 . ?
C7 C6 1.475(12) . ?
C6 C5 1.209(15) . ?
C6 C1 1.289(14) . ?
C5 C4 1.41(2) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C2 C1 1.45(2) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C23 C12 1.391(13) . ?
C23 H13 0.9300 . ?
C12 O1 1.398(11) . ?
C13 O1 1.372(12) . ?
S1 O3 1.330(7) . ?
S1 C25 1.486(18) . ?
S1 C24 1.625(14) . ?
C24 H21 0.9600 . ?
C24 H20 0.9600 . ?
C24 H22 0.9600 . ?
C25 H18 0.9611 . ?
C25 H17 0.9611 . ?
C25 H19 0.9611 . ?

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
C2 C3 C4 116.1(14) . . ?
C2 C3 H3 122.0 . . ?
C4 C3 H3 122.0 . . ?
C10 N1 C7 110.1(6) . . ?
C10 N1 H6 125.0 . . ?
C7 N1 H6 125.0 . . ?
C18 C17 C16 120.7(8) . . ?
C18 C17 H10 119.7 . . ?
C16 C17 H10 119.7 . . ?
C17 C16 C15 119.5(8) . . ?
C17 C16 H9 120.3 . . ?
C15 C16 H9 120.3 . . ?
C14 C15 C16 120.3(8) . . ?
C14 C15 H8 119.9 . . ?
C16 C15 H8 119.9 . . ?
C15 C14 C19 119.6(7) . . ?
C15 C14 N2 118.0(7) . . ?
C19 C14 N2 122.4(7) . . ?
C8 N2 C14 122.1(6) . . ?
C8 N2 H7 119.0 . . ?
C14 N2 H7 119.0 . . ?
C7 C8 N2 126.6(9) . . ?
C7 C8 C9 106.5(7) . . ?
N2 C8 C9 126.9(7) . . ?
C10 C9 C8 108.5(7) . . ?
C10 C9 C13 120.4(9) . . ?
C8 C9 C13 131.0(8) . . ?
N1 C10 C9 107.7(8) . . ?
N1 C10 C11 129.1(7) . . ?
C9 C10 C11 123.1(8) . . ?
C20 C11 C12 118.7(8) . . ?
C20 C11 C10 126.6(7) . . ?
C12 C11 C10 114.6(8) . . ?
C21 C20 C11 119.7(8) . . ?
C21 C20 H16 120.2 . . ?
C11 C20 H16 120.2 . . ?
C20 C21 C22 120.3(10) . . ?
C20 C21 H15 119.8 . . ?
C22 C21 H15 119.8 . . ?
C23 C22 C21 121.3(10) . . ?
C23 C22 H14 119.4 . . ?
C21 C22 H14 119.4 . . ?
C17 C18 C19 119.5(8) . . ?
C17 C18 H11 120.3 . . ?
C19 C18 H11 120.3 . . ?
C14 C19 C18 120.3(8) . . ?
C14 C19 H12 119.8 . . ?
C18 C19 H12 119.8 . . ?
N1 C7 C8 107.2(8) . . ?
N1 C7 C6 121.5(7) . . ?
C8 C7 C6 131.2(8) . . ?
C5 C6 C1 116.3(14) . . ?
C5 C6 C7 122.8(11) . . ?
C1 C6 C7 120.8(10) . . ?
C6 C5 C4 124.3(15) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C3 C4 C5 119.0(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C3 C2 C1 121.8(17) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C6 C1 C2 119.6(14) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C22 C23 C12 118.2(9) . . ?
C22 C23 H13 120.9 . . ?
C12 C23 H13 120.9 . . ?
C23 C12 C11 121.7(9) . . ?
C23 C12 O1 116.3(8) . . ?
C11 C12 O1 122.0(9) . . ?
O2 C13 O1 116.3(9) . . ?
O2 C13 C9 127.4(11) . . ?
O1 C13 C9 116.3(8) . . ?
C13 O1 C12 123.6(7) . . ?
O3 S1 C25 126.1(9) . . ?
O3 S1 C24 122.4(9) . . ?
C25 S1 C24 108.4(12) . . ?
S1 C24 H21 109.5 . . ?
S1 C24 H20 109.5 . . ?
H21 C24 H20 109.5 . . ?
S1 C24 H22 109.5 . . ?
H21 C24 H22 109.5 . . ?
H20 C24 H22 109.5 . . ?
S1 C25 H18 109.6 . . ?
S1 C25 H17 109.5 . . ?
H18 C25 H17 109.4 . . ?
S1 C25 H19 109.6 . . ?
H18 C25 H19 109.4 . . ?
H17 C25 H19 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.95
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.946
_refine_diff_density_min         -1.757
_refine_diff_density_rms         0.109
