# 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_Kuwar1994
_database_code_depnum_ccdc_archive 'CCDC 999181'
_audit_update_record             
;
2014-04-24 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_date             2014-03-07T17:24:51-00:00
_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         'C20 H15 N3 O3 S2'
_chemical_formula_sum            'C20 H15 N3 O3 S2'
_chemical_formula_weight         409.47

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2244(2)
_cell_length_b                   10.6450(2)
_cell_length_c                   10.7022(2)
_cell_angle_alpha                117.291(1)
_cell_angle_beta                 104.012(1)
_cell_angle_gamma                102.864(1)
_cell_volume                     926.11(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      2.04
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_special_details           
;All work was done at 150 K using an Oxford Cryosystems 
 Cryostream Cooler.  

The data collection strategy was set up to measure a hemisphere of 
reciprocal space with a redundancy factor of 3.6, which means that 90%
of the data was measured at least 3.6 times. Phi and omega scans 
with a frame width of 1.0 degree were used.
Data integration was done with Denzo, and scaling and merging
of the data was done with Scalepack. 
;

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

_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.060464
_diffrn_orient_matrix_ub_12      0.007299
_diffrn_orient_matrix_ub_13      0.061925
_diffrn_orient_matrix_ub_21      -0.033862
_diffrn_orient_matrix_ub_22      -0.113092
_diffrn_orient_matrix_ub_23      -0.045971
_diffrn_orient_matrix_ub_31      0.084549
_diffrn_orient_matrix_ub_32      0.017283
_diffrn_orient_matrix_ub_33      0.084728
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_number            28487
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             4233
_reflns_number_gt                3237
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;For the C(20) methyl group, the hydrogen atoms were added at 
 calculated positions using a riding model with 
 U(H) = 1.5 * Ueq(bonded carbon atom).  The torsion angle, which defines 
 the orientation of this methyl group about the C-C bond, was refined. 
 The rest of the hydrogen atoms were included in
 the model at calculated positions using a riding model with 
 U(H) = 1.2 * Ueq(bonded atom).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.2493P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4233
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   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
C2 C 0.92498(17) 0.72227(18) 0.87022(18) 0.0223(3) Uani 1 d . .
C4 C 1.13641(17) 0.89791(18) 0.94074(18) 0.0234(4) Uani 1 d . .
C5 C 1.05497(18) 0.89852(18) 0.81452(18) 0.0246(4) Uani 1 d . .
C6 C 1.11807(19) 0.99601(19) 0.7739(2) 0.0292(4) Uani 1 d . .
H6 H 1.0625 0.996 0.6887 0.035 Uiso 1 calc . .
C7 C 1.2637(2) 1.09295(19) 0.8605(2) 0.0295(4) Uani 1 d . .
H7 H 1.3082 1.1618 0.8357 0.035 Uiso 1 calc . .
C8 C 1.34586(19) 1.0909(2) 0.9834(2) 0.0318(4) Uani 1 d . .
H8 H 1.4463 1.1571 1.0401 0.038 Uiso 1 calc . .
C9 C 1.28392(19) 0.99440(19) 1.02415(19) 0.0307(4) Uani 1 d . .
H9 H 1.3411 0.9937 1.1081 0.037 Uiso 1 calc . .
C11 C 0.83882(16) 0.58447(17) 0.96782(18) 0.0213(3) Uani 1 d . .
C13 C 0.91451(16) 0.56014(17) 1.19414(18) 0.0217(3) Uani 1 d . .
C14 C 0.76518(17) 0.44705(18) 1.07728(18) 0.0221(3) Uani 1 d . .
C16 C 0.97614(18) 0.56109(18) 1.32034(18) 0.0244(4) Uani 1 d . .
H16 H 0.9225 0.4913 1.3391 0.029 Uiso 1 calc . .
C17 C 1.12612(18) 0.66931(19) 1.42984(18) 0.0244(4) Uani 1 d . .
C19 C 1.32858(18) 0.7350(2) 1.64542(19) 0.0298(4) Uani 1 d . .
H19A H 1.3429 0.7424 1.7438 0.036 Uiso 1 calc . .
H19B H 1.3555 0.84 1.6662 0.036 Uiso 1 calc . .
C20 C 1.42479(19) 0.6632(2) 1.5779(2) 0.0372(4) Uani 1 d . .
H20A H 1.4151 0.6621 1.484 0.056 Uiso 1 calc . .
H20B H 1.3954 0.5579 1.5538 0.056 Uiso 1 calc . .
H20C H 1.5267 0.7227 1.6518 0.056 Uiso 1 calc . .
C22 C 0.59346(16) 0.37069(18) 0.82503(17) 0.0217(3) Uani 1 d . .
C23 C 0.49495(18) 0.4329(2) 0.79301(19) 0.0264(4) Uani 1 d . .
H23 H 0.5176 0.5396 0.8557 0.032 Uiso 1 calc . .
C24 C 0.36207(19) 0.3367(2) 0.6676(2) 0.0328(4) Uani 1 d . .
H24 H 0.2937 0.3779 0.643 0.039 Uiso 1 calc . .
C25 C 0.32921(19) 0.1810(2) 0.57837(19) 0.0341(4) Uani 1 d . .
H25 H 0.2379 0.1155 0.4934 0.041 Uiso 1 calc . .
C26 C 0.42873(19) 0.1204(2) 0.6125(2) 0.0331(4) Uani 1 d . .
H26 H 0.4052 0.0134 0.5514 0.04 Uiso 1 calc . .
C27 C 0.56291(18) 0.21566(19) 0.73570(19) 0.0268(4) Uani 1 d . .
H27 H 0.6326 0.175 0.7583 0.032 Uiso 1 calc . .
N3 N 1.05923(14) 0.79748(15) 0.96997(15) 0.0251(3) Uani 1 d . .
N10 N 0.81614(14) 0.60949(15) 0.86011(15) 0.0231(3) Uani 1 d . .
N15 N 0.73084(13) 0.46837(15) 0.95661(14) 0.0213(3) Uani 1 d . .
O18 O 1.17492(12) 0.64308(13) 1.53948(12) 0.0277(3) Uani 1 d . .
O21 O 0.68426(12) 0.35147(13) 1.08521(13) 0.0274(3) Uani 1 d . .
O28 O 1.19665(13) 0.76899(13) 1.41852(13) 0.0316(3) Uani 1 d . .
S1 S 0.87747(5) 0.76476(5) 0.73010(5) 0.02960(13) Uani 1 d . .
S12 S 0.99529(4) 0.68024(4) 1.14106(4) 0.02256(11) 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
C2 N3 1.297(2) . ?
C2 N10 1.385(2) . ?
C2 S1 1.7483(16) . ?
C4 N3 1.383(2) . ?
C4 C9 1.394(2) . ?
C4 C5 1.409(2) . ?
C5 C6 1.391(2) . ?
C5 S1 1.7358(17) . ?
C6 C7 1.383(2) . ?
C6 H6 0.95 . ?
C7 C8 1.391(3) . ?
C7 H7 0.95 . ?
C8 C9 1.379(2) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C11 N10 1.278(2) . ?
C11 N15 1.398(2) . ?
C11 S12 1.7721(16) . ?
C13 C16 1.339(2) . ?
C13 C14 1.490(2) . ?
C13 S12 1.7499(16) . ?
C14 O21 1.2105(19) . ?
C14 N15 1.388(2) . ?
C16 C17 1.469(2) . ?
C16 H16 0.95 . ?
C17 O28 1.2166(19) . ?
C17 O18 1.3351(19) . ?
C19 O18 1.4652(19) . ?
C19 C20 1.499(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C22 C23 1.382(2) . ?
C22 C27 1.384(2) . ?
C22 N15 1.4444(19) . ?
C23 C24 1.391(2) . ?
C23 H23 0.95 . ?
C24 C25 1.385(3) . ?
C24 H24 0.95 . ?
C25 C26 1.383(3) . ?
C25 H25 0.95 . ?
C26 C27 1.388(2) . ?
C26 H26 0.95 . ?
C27 H27 0.95 . ?

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
N3 C2 N10 127.27(14) . . ?
N3 C2 S1 116.28(12) . . ?
N10 C2 S1 116.43(11) . . ?
N3 C4 C9 125.61(15) . . ?
N3 C4 C5 115.13(14) . . ?
C9 C4 C5 119.26(15) . . ?
C6 C5 C4 121.24(15) . . ?
C6 C5 S1 129.51(13) . . ?
C4 C5 S1 109.25(12) . . ?
C7 C6 C5 118.35(16) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C8 120.83(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.07(16) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C4 119.22(16) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
N10 C11 N15 119.77(14) . . ?
N10 C11 S12 128.70(12) . . ?
N15 C11 S12 111.53(11) . . ?
C16 C13 C14 121.73(14) . . ?
C16 C13 S12 126.30(12) . . ?
C14 C13 S12 111.93(11) . . ?
O21 C14 N15 124.45(14) . . ?
O21 C14 C13 125.93(15) . . ?
N15 C14 C13 109.62(13) . . ?
C13 C16 C17 120.44(15) . . ?
C13 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
O28 C17 O18 124.86(15) . . ?
O28 C17 C16 122.99(15) . . ?
O18 C17 C16 112.14(14) . . ?
O18 C19 C20 110.17(14) . . ?
O18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
O18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C22 C27 121.66(15) . . ?
C23 C22 N15 119.64(14) . . ?
C27 C22 N15 118.69(14) . . ?
C22 C23 C24 118.87(16) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.09(17) . . ?
C25 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
C26 C25 C24 120.30(16) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.18(17) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 118.89(16) . . ?
C22 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C2 N3 C4 110.54(13) . . ?
C11 N10 C2 119.47(14) . . ?
C14 N15 C11 116.10(13) . . ?
C14 N15 C22 121.15(13) . . ?
C11 N15 C22 122.70(13) . . ?
C17 O18 C19 116.24(13) . . ?
C5 S1 C2 88.78(8) . . ?
C13 S12 C11 90.80(7) . . ?

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
N3 C4 C5 C6 178.77(15) . . . . ?
C9 C4 C5 C6 -1.5(2) . . . . ?
N3 C4 C5 S1 -1.27(18) . . . . ?
C9 C4 C5 S1 178.45(13) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
S1 C5 C6 C7 -179.83(13) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
N3 C4 C9 C8 -178.78(16) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C16 C13 C14 O21 2.8(3) . . . . ?
S12 C13 C14 O21 -179.29(13) . . . . ?
C16 C13 C14 N15 -177.86(14) . . . . ?
S12 C13 C14 N15 0.06(16) . . . . ?
C14 C13 C16 C17 177.13(14) . . . . ?
S12 C13 C16 C17 -0.5(2) . . . . ?
C13 C16 C17 O28 5.7(3) . . . . ?
C13 C16 C17 O18 -173.27(14) . . . . ?
C27 C22 C23 C24 -0.1(2) . . . . ?
N15 C22 C23 C24 -178.81(14) . . . . ?
C22 C23 C24 C25 1.0(2) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C27 -0.6(3) . . . . ?
C23 C22 C27 C26 -1.1(2) . . . . ?
N15 C22 C27 C26 177.62(14) . . . . ?
C25 C26 C27 C22 1.4(2) . . . . ?
N10 C2 N3 C4 178.32(15) . . . . ?
S1 C2 N3 C4 0.03(18) . . . . ?
C9 C4 N3 C2 -178.88(16) . . . . ?
C5 C4 N3 C2 0.8(2) . . . . ?
N15 C11 N10 C2 -178.45(13) . . . . ?
S12 C11 N10 C2 1.9(2) . . . . ?
N3 C2 N10 C11 9.2(2) . . . . ?
S1 C2 N10 C11 -172.55(12) . . . . ?
O21 C14 N15 C11 -179.83(15) . . . . ?
C13 C14 N15 C11 0.80(19) . . . . ?
O21 C14 N15 C22 -2.4(2) . . . . ?
C13 C14 N15 C22 178.22(13) . . . . ?
N10 C11 N15 C14 178.96(14) . . . . ?
S12 C11 N15 C14 -1.31(17) . . . . ?
N10 C11 N15 C22 1.6(2) . . . . ?
S12 C11 N15 C22 -178.68(11) . . . . ?
C23 C22 N15 C14 116.76(17) . . . . ?
C27 C22 N15 C14 -62.0(2) . . . . ?
C23 C22 N15 C11 -66.0(2) . . . . ?
C27 C22 N15 C11 115.25(17) . . . . ?
O28 C17 O18 C19 -4.9(2) . . . . ?
C16 C17 O18 C19 174.04(13) . . . . ?
C20 C19 O18 C17 -84.01(18) . . . . ?
C6 C5 S1 C2 -179.02(17) . . . . ?
C4 C5 S1 C2 1.01(12) . . . . ?
N3 C2 S1 C5 -0.64(13) . . . . ?
N10 C2 S1 C5 -179.12(13) . . . . ?
C16 C13 S12 C11 177.16(15) . . . . ?
C14 C13 S12 C11 -0.65(12) . . . . ?
N10 C11 S12 C13 -179.21(16) . . . . ?
N15 C11 S12 C13 1.09(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O18 0.95 2.53 3.461(2) 165.1 2_768
C19 H19A O21 0.99 2.49 3.426(2) 156.6 2_768
C23 H23 O21 0.95 2.65 3.257(2) 122.1 2_667


# END of CIF
