# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_shx97
_database_code_depnum_ccdc_archive 'CCDC 1414713'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 N O2 S'
_chemical_formula_sum            'C19 H11 N O2 S'
_chemical_formula_weight         317.35

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.242(2)
_cell_length_b                   11.566(2)
_cell_length_c                   10.526(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.08(3)
_cell_angle_gamma                90.00
_cell_volume                     1488.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9100
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         image
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11840
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2719
_reflns_number_gt                2083
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97

_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)+(0.0488P)²+0.3027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61831(4) 0.65075(4) 1.01969(5) 0.0571(2) Uani 1 1 d . . .
O1 O 0.69326(12) 0.44392(14) 0.63848(16) 0.0760(5) Uani 1 1 d . . .
O2 O 0.69825(14) 0.68436(13) 0.75567(16) 0.0735(5) Uani 1 1 d . . .
N1 N 0.68668(13) 0.44526(13) 0.96270(15) 0.0513(4) Uani 1 1 d . . .
C1 C 1.1130(2) 0.34028(18) 0.5604(2) 0.0638(6) Uani 1 1 d . . .
H1A H 1.1888 0.3371 0.5719 0.077 Uiso 1 1 calc R . .
C2 C 1.0624(2) 0.28436(18) 0.4611(2) 0.0724(7) Uani 1 1 d . . .
H2A H 1.1033 0.2431 0.4045 0.087 Uiso 1 1 calc R . .
C3 C 0.9489(2) 0.28861(18) 0.4437(2) 0.0695(7) Uani 1 1 d . . .
H3A H 0.9147 0.2491 0.3757 0.083 Uiso 1 1 calc R . .
C4 C 0.88622(19) 0.34958(16) 0.52445(19) 0.0571(5) Uani 1 1 d . . .
H4A H 0.8106 0.3519 0.5100 0.069 Uiso 1 1 calc R . .
C5 C 0.93613(16) 0.40906(15) 0.62984(17) 0.0464(4) Uani 1 1 d . . .
C6 C 1.05213(17) 0.40361(16) 0.64692(18) 0.0516(5) Uani 1 1 d . . .
C7 C 1.10555(18) 0.46358(19) 0.7488(2) 0.0603(5) Uani 1 1 d . . .
H7A H 1.1814 0.4593 0.7594 0.072 Uiso 1 1 calc R . .
C8 C 1.05000(17) 0.52727(19) 0.8318(2) 0.0584(5) Uani 1 1 d . . .
H8A H 1.0871 0.5657 0.8988 0.070 Uiso 1 1 calc R . .
C9 C 0.93633(16) 0.53452(17) 0.81556(17) 0.0510(5) Uani 1 1 d . . .
H9A H 0.8984 0.5790 0.8722 0.061 Uiso 1 1 calc R . .
C10 C 0.87834(15) 0.47796(15) 0.71847(17) 0.0449(4) Uani 1 1 d . . .
C11 C 0.75942(17) 0.49350(17) 0.71009(19) 0.0520(5) Uani 1 1 d . . .
C12 C 0.71007(16) 0.58630(18) 0.79463(19) 0.0530(5) Uani 1 1 d . . .
C13 C 0.67357(15) 0.55026(16) 0.91928(18) 0.0479(5) Uani 1 1 d . . .
C14 C 0.64994(15) 0.43859(16) 1.08446(19) 0.0497(5) Uani 1 1 d . . .
C15 C 0.65339(18) 0.33969(19) 1.1599(2) 0.0642(6) Uani 1 1 d . . .
H15A H 0.6797 0.2703 1.1289 0.077 Uiso 1 1 calc R . .
C16 C 0.61719(19) 0.3465(2) 1.2806(2) 0.0727(7) Uani 1 1 d . . .
H16A H 0.6197 0.2814 1.3325 0.087 Uiso 1 1 calc R . .
C17 C 0.57664(19) 0.4502(2) 1.3265(2) 0.0748(7) Uani 1 1 d . . .
H17A H 0.5521 0.4525 1.4085 0.090 Uiso 1 1 calc R . .
C18 C 0.57183(18) 0.5485(2) 1.2544(2) 0.0663(6) Uani 1 1 d . . .
H18A H 0.5443 0.6170 1.2861 0.080 Uiso 1 1 calc R . .
C19 C 0.60961(15) 0.54286(17) 1.13179(19) 0.0511(5) Uani 1 1 d . . .


_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 C19 1.725(2) . ?
S1 C13 1.7327(19) . ?
O1 C11 1.220(2) . ?
O2 C12 1.212(2) . ?
N1 C13 1.304(2) . ?
N1 C14 1.383(3) . ?
C1 C2 1.350(3) . ?
C1 C6 1.412(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.416(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.423(3) . ?
C5 C10 1.441(2) . ?
C6 C7 1.409(3) . ?
C7 C8 1.354(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.395(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.465(3) . ?
C11 C12 1.538(3) . ?
C12 C13 1.469(3) . ?
C14 C15 1.392(3) . ?
C14 C19 1.405(3) . ?
C15 C16 1.371(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.393(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.366(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.396(3) . ?
C18 H18A 0.9300 . ?

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
C19 S1 C13 88.43(9) . . ?
C13 N1 C14 109.67(16) . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 117.59(18) . . ?
C4 C5 C10 124.73(19) . . ?
C6 C5 C10 117.65(17) . . ?
C7 C6 C1 120.5(2) . . ?
C7 C6 C5 119.57(18) . . ?
C1 C6 C5 119.9(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
C7 C8 C9 119.07(19) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C10 C9 C8 122.22(18) . . ?
C10 C9 H9A 118.9 . . ?
C8 C9 H9A 118.9 . . ?
C9 C10 C5 119.43(18) . . ?
C9 C10 C11 117.20(17) . . ?
C5 C10 C11 123.36(17) . . ?
O1 C11 C10 127.17(19) . . ?
O1 C11 C12 114.66(18) . . ?
C10 C11 C12 118.09(17) . . ?
O2 C12 C13 122.09(19) . . ?
O2 C12 C11 120.04(19) . . ?
C13 C12 C11 117.80(17) . . ?
N1 C13 C12 122.65(17) . . ?
N1 C13 S1 117.09(15) . . ?
C12 C13 S1 120.13(15) . . ?
N1 C14 C15 124.95(18) . . ?
N1 C14 C19 114.76(17) . . ?
C15 C14 C19 120.26(19) . . ?
C16 C15 C14 118.7(2) . . ?
C16 C15 H15A 120.7 . . ?
C14 C15 H15A 120.7 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17A 119.0 . . ?
C16 C17 H17A 119.0 . . ?
C17 C18 C19 117.9(2) . . ?
C17 C18 H18A 121.1 . . ?
C19 C18 H18A 121.1 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 S1 129.38(17) . . ?
C14 C19 S1 110.04(15) . . ?

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 -0.2(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C10 178.34(18) . . . . ?
C2 C1 C6 C7 -178.77(19) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C4 C5 C6 C7 178.59(17) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C10 C5 C6 C1 -178.01(17) . . . . ?
C1 C6 C7 C8 178.45(19) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.15(18) . . . . ?
C4 C5 C10 C9 -178.20(17) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C4 C5 C10 C11 0.6(3) . . . . ?
C6 C5 C10 C11 178.39(17) . . . . ?
C9 C10 C11 O1 -173.5(2) . . . . ?
C5 C10 C11 O1 7.7(3) . . . . ?
C9 C10 C11 C12 10.0(3) . . . . ?
C5 C10 C11 C12 -168.89(17) . . . . ?
O1 C11 C12 O2 -87.0(3) . . . . ?
C10 C11 C12 O2 90.0(2) . . . . ?
O1 C11 C12 C13 90.0(2) . . . . ?
C10 C11 C12 C13 -93.0(2) . . . . ?
C14 N1 C13 C12 176.77(17) . . . . ?
C14 N1 C13 S1 0.9(2) . . . . ?
O2 C12 C13 N1 -179.40(19) . . . . ?
C11 C12 C13 N1 3.7(3) . . . . ?
O2 C12 C13 S1 -3.6(3) . . . . ?
C11 C12 C13 S1 179.45(14) . . . . ?
C19 S1 C13 N1 -0.69(16) . . . . ?
C19 S1 C13 C12 -176.71(16) . . . . ?
C13 N1 C14 C15 -178.91(19) . . . . ?
C13 N1 C14 C19 -0.6(2) . . . . ?
N1 C14 C15 C16 177.9(2) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C17 C18 C19 S1 -178.03(17) . . . . ?
N1 C14 C19 C18 -178.83(18) . . . . ?
C15 C14 C19 C18 -0.4(3) . . . . ?
N1 C14 C19 S1 0.1(2) . . . . ?
C15 C14 C19 S1 178.51(16) . . . . ?
C13 S1 C19 C18 179.1(2) . . . . ?
C13 S1 C19 C14 0.28(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041

