# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1049804'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_date             2014-09-09T14:26:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_Int_Tables_number      88
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   29.160(4)
_cell_length_b                   29.160(4)
_cell_length_c                   8.7046(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7402(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    51827
_cell_measurement_theta_min      1.397
_cell_measurement_theta_max      28.31
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3040
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.962
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.962

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   graphite
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_number            51827
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.397
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_number_total             4530
_reflns_number_gt                3851
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0586P)²+6.2649P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4530
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.56388(7) -0.02470(7) 0.8838(3) 0.0529(5) Uani 1 d . .
H1A H 0.5662 -0.0584 0.8967 0.064 Uiso 1 calc . .
H1B H 0.5668 -0.0104 0.9865 0.064 Uiso 1 calc . .
C2 C 0.60260(6) -0.00824(6) 0.7821(2) 0.0448(4) Uani 1 d . .
H2A H 0.6325 -0.0158 0.8294 0.054 Uiso 1 calc . .
H2B H 0.6009 -0.0233 0.6804 0.054 Uiso 1 calc . .
C3 C 0.63185(7) 0.14087(6) 0.8542(2) 0.0464(4) Uani 1 d . .
H3 H 0.6502 0.1274 0.9322 0.056 Uiso 1 calc . .
C4 C 0.60692(7) 0.17732(6) 0.8882(2) 0.0469(4) Uani 1 d . .
H4 H 0.5873 0.1886 0.8099 0.056 Uiso 1 calc . .
C5 C 0.60656(6) 0.20205(6) 1.0352(2) 0.0415(4) Uani 1 d . .
C6 C 0.63771(6) 0.19392(6) 1.1534(2) 0.0457(4) Uani 1 d . .
H6 H 0.6611 0.1716 1.1387 0.055 Uiso 1 calc . .
C7 C 0.63567(7) 0.21745(6) 1.2920(2) 0.0459(4) Uani 1 d . .
H7 H 0.6574 0.2113 1.3707 0.055 Uiso 1 calc . .
C8 C 0.60159(6) 0.25003(6) 1.3146(2) 0.0438(4) Uani 1 d . .
C9 C 0.62426(8) 0.26289(9) 1.5738(3) 0.0640(6) Uani 1 d . .
H9A H 0.6171 0.283 1.6608 0.096 Uiso 1 calc . .
H9B H 0.6566 0.2666 1.5453 0.096 Uiso 1 calc . .
H9C H 0.6186 0.2309 1.6028 0.096 Uiso 1 calc . .
C10 C 0.64756(10) 0.03302(10) 0.1925(2) 0.0713(7) Uani 1 d . .
H10 H 0.6481 0.0243 0.0873 0.086 Uiso 1 calc . .
C11 C 0.62390(9) 0.07133(10) 0.2367(3) 0.0679(6) Uani 1 d . .
H11 H 0.6084 0.0891 0.1614 0.082 Uiso 1 calc . .
C12 C 0.62214(7) 0.08465(8) 0.3900(2) 0.0538(5) Uani 1 d . .
H12 H 0.6055 0.1111 0.4205 0.065 Uiso 1 calc . .
C13 C 0.64536(6) 0.05815(6) 0.4970(2) 0.0425(4) Uani 1 d . .
C14 C 0.57326(7) 0.23557(6) 1.0615(2) 0.0506(4) Uani 1 d . .
H14 H 0.5518 0.2424 0.9825 0.061 Uiso 1 calc . .
C15 C 0.57051(7) 0.25898(7) 1.1983(2) 0.0519(5) Uani 1 d . .
H15 H 0.5472 0.2813 1.213 0.062 Uiso 1 calc . .
C16 C 0.51591(7) 0.03473(7) 0.8063(3) 0.0592(6) Uani 1 d . .
H16A H 0.5182 0.049 0.9092 0.071 Uiso 1 calc . .
H16B H 0.4853 0.0421 0.7638 0.071 Uiso 1 calc . .
C17 C 0.55272(6) 0.05447(6) 0.7024(2) 0.0485(4) Uani 1 d . .
H17A H 0.5493 0.0421 0.5971 0.058 Uiso 1 calc . .
H17B H 0.5498 0.0883 0.6976 0.058 Uiso 1 calc . .
C18 C 0.66976(9) 0.01954(7) 0.4543(2) 0.0580(5) Uani 1 d . .
H18 H 0.6857 0.0019 0.5289 0.07 Uiso 1 calc . .
C19 C 0.67055(11) 0.00699(9) 0.2996(3) 0.0721(7) Uani 1 d . .
H19 H 0.687 -0.0195 0.2682 0.087 Uiso 1 calc . .
N1 N 0.59798(5) 0.04175(5) 0.76503(16) 0.0385(3) Uani 1 d . .
N2 N 0.63214(6) 0.12113(5) 0.70445(17) 0.0475(4) Uani 1 d . .
O1 O 0.52039(5) -0.01359(5) 0.82056(18) 0.0563(4) Uani 1 d . .
O2 O 0.59614(5) 0.27470(5) 1.44717(17) 0.0574(4) Uani 1 d . .
O3 O 0.68177(5) 0.05020(5) 0.77150(15) 0.0506(3) Uani 1 d . .
S1 S 0.64258(2) 0.07017(2) 0.69566(5) 0.03931(13) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.420(2) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 N1 1.472(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.321(3) . ?
C3 N2 1.425(2) . ?
C3 H3 0.95 . ?
C4 C5 1.469(3) . ?
C4 H4 0.95 . ?
C5 C6 1.393(3) . ?
C5 C14 1.397(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.95 . ?
C7 C8 1.389(2) . ?
C7 H7 0.95 . ?
C8 O2 1.369(2) . ?
C8 C15 1.384(3) . ?
C9 O2 1.416(3) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.368(4) . ?
C10 C19 1.376(4) . ?
C10 H10 0.95 . ?
C11 C12 1.390(3) . ?
C11 H11 0.95 . ?
C12 C13 1.387(3) . ?
C12 H12 0.95 . ?
C13 C18 1.383(3) . ?
C13 S1 1.7666(18) . ?
C14 C15 1.375(3) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 O1 1.421(2) . ?
C16 C17 1.517(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 N1 1.476(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.395(3) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
N1 S1 1.6561(14) . ?
N2 S1 1.5189(16) . ?
O3 S1 1.4424(14) . ?

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 C1 C2 111.59(16) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108 . . ?
N1 C2 C1 107.77(15) . . ?
N1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
N1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C4 C3 N2 122.21(19) . . ?
C4 C3 H3 118.9 . . ?
N2 C3 H3 118.9 . . ?
C3 C4 C5 126.46(18) . . ?
C3 C4 H4 116.8 . . ?
C5 C4 H4 116.8 . . ?
C6 C5 C14 116.83(17) . . ?
C6 C5 C4 123.71(17) . . ?
C14 C5 C4 119.45(17) . . ?
C7 C6 C5 121.97(17) . . ?
C7 C6 H6 119 . . ?
C5 C6 H6 119 . . ?
C8 C7 C6 119.44(18) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O2 C8 C15 116.20(16) . . ?
O2 C8 C7 124.19(17) . . ?
C15 C8 C7 119.61(18) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C19 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C19 C10 H10 119.8 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 121 . . ?
C11 C12 H12 121 . . ?
C18 C13 C12 121.64(18) . . ?
C18 C13 S1 116.63(15) . . ?
C12 C13 S1 121.64(16) . . ?
C15 C14 C5 122.01(18) . . ?
C15 C14 H14 119 . . ?
C5 C14 H14 119 . . ?
C14 C15 C8 120.13(18) . . ?
C14 C15 H15 119.9 . . ?
C8 C15 H15 119.9 . . ?
O1 C16 C17 111.30(17) . . ?
O1 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
O1 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
N1 C17 C16 108.48(15) . . ?
N1 C17 H17A 110 . . ?
C16 C17 H17A 110 . . ?
N1 C17 H17B 110 . . ?
C16 C17 H17B 110 . . ?
H17A C17 H17B 108.4 . . ?
C13 C18 C19 118.8(2) . . ?
C13 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C10 C19 C18 120.1(2) . . ?
C10 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C2 N1 C17 111.60(14) . . ?
C2 N1 S1 117.43(12) . . ?
C17 N1 S1 116.23(11) . . ?
C3 N2 S1 116.25(13) . . ?
C1 O1 C16 110.00(15) . . ?
C8 O2 C9 117.44(15) . . ?
O3 S1 N2 122.06(9) . . ?
O3 S1 N1 104.67(8) . . ?
N2 S1 N1 108.29(8) . . ?
O3 S1 C13 109.37(9) . . ?
N2 S1 C13 104.64(9) . . ?
N1 S1 C13 107.08(8) . . ?

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
O1 C1 C2 N1 58.8(2) . . . . ?
N2 C3 C4 C5 -175.57(16) . . . . ?
C3 C4 C5 C6 9.3(3) . . . . ?
C3 C4 C5 C14 -170.14(19) . . . . ?
C14 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C7 -178.71(17) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 O2 179.15(18) . . . . ?
C6 C7 C8 C15 -0.7(3) . . . . ?
C19 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C18 0.1(3) . . . . ?
C11 C12 C13 S1 -176.29(16) . . . . ?
C6 C5 C14 C15 -1.2(3) . . . . ?
C4 C5 C14 C15 178.29(18) . . . . ?
C5 C14 C15 C8 0.7(3) . . . . ?
O2 C8 C15 C14 -179.58(18) . . . . ?
C7 C8 C15 C14 0.3(3) . . . . ?
O1 C16 C17 N1 -57.2(2) . . . . ?
C12 C13 C18 C19 -0.5(3) . . . . ?
S1 C13 C18 C19 176.03(19) . . . . ?
C11 C10 C19 C18 0.1(4) . . . . ?
C13 C18 C19 C10 0.4(4) . . . . ?
C1 C2 N1 C17 -56.8(2) . . . . ?
C1 C2 N1 S1 165.33(13) . . . . ?
C16 C17 N1 C2 56.4(2) . . . . ?
C16 C17 N1 S1 -165.23(14) . . . . ?
C4 C3 N2 S1 -152.46(16) . . . . ?
C2 C1 O1 C16 -61.0(2) . . . . ?
C17 C16 O1 C1 59.9(2) . . . . ?
C15 C8 O2 C9 173.44(19) . . . . ?
C7 C8 O2 C9 -6.4(3) . . . . ?
C3 N2 S1 O3 -50.28(17) . . . . ?
C3 N2 S1 N1 71.16(16) . . . . ?
C3 N2 S1 C13 -174.89(14) . . . . ?
C2 N1 S1 O3 -42.26(15) . . . . ?
C17 N1 S1 O3 -178.18(13) . . . . ?
C2 N1 S1 N2 -173.89(13) . . . . ?
C17 N1 S1 N2 50.20(15) . . . . ?
C2 N1 S1 C13 73.78(15) . . . . ?
C17 N1 S1 C13 -62.13(15) . . . . ?
C18 C13 S1 O3 25.36(18) . . . . ?
C12 C13 S1 O3 -158.09(15) . . . . ?
C18 C13 S1 N2 157.68(16) . . . . ?
C12 C13 S1 N2 -25.77(18) . . . . ?
C18 C13 S1 N1 -87.52(17) . . . . ?
C12 C13 S1 N1 89.03(16) . . . . ?


# END of CIF
