# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a15780
_database_code_depnum_ccdc_archive 'CCDC 1511556'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2'
_chemical_formula_sum            'C15 H10 N2'
_chemical_formula_weight         218.25

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   13.936(7)
_cell_length_b                   7.077(3)
_cell_length_c                   22.807(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2249.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    491
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      18.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15611
_diffrn_reflns_av_R_equivalents  0.1822
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.19
_reflns_number_total             2016
_reflns_number_gt                1116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0585P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2016
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_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
C1 C 0.0725(2) 0.6898(4) 0.40901(11) 0.0364(7) Uani 1 1 d . . .
C2 C 0.1117(2) 0.9035(4) 0.48806(11) 0.0325(7) Uani 1 1 d . . .
C3 C 0.0852(2) 0.7998(4) 0.53637(12) 0.0373(8) Uani 1 1 d . . .
H3 H 0.0552 0.6798 0.5329 0.045 Uiso 1 1 calc R . .
C4 C 0.1048(2) 0.8802(4) 0.59046(12) 0.0426(8) Uani 1 1 d . . .
H4 H 0.0880 0.8138 0.6252 0.051 Uiso 1 1 calc R . .
C5 C 0.1485(2) 1.0561(4) 0.59487(12) 0.0442(8) Uani 1 1 d . . .
H5 H 0.1619 1.1067 0.6326 0.053 Uiso 1 1 calc R . .
C6 C 0.1728(2) 1.1584(4) 0.54586(12) 0.0418(8) Uani 1 1 d . . .
H6 H 0.2011 1.2800 0.5495 0.050 Uiso 1 1 calc R . .
C7 C 0.15509(19) 1.0809(4) 0.49081(11) 0.0335(7) Uani 1 1 d . . .
C8 C 0.1705(2) 1.1441(4) 0.43161(11) 0.0352(7) Uani 1 1 d . . .
H8 H 0.1993 1.2606 0.4207 0.042 Uiso 1 1 calc R . .
C9 C 0.1374(2) 1.0114(4) 0.39376(11) 0.0325(7) Uani 1 1 d . . .
C10 C 0.1338(2) 1.0111(4) 0.32957(11) 0.0332(7) Uani 1 1 d . . .
C11 C 0.2066(2) 1.0992(4) 0.29844(12) 0.0455(8) Uani 1 1 d . . .
H11 H 0.2590 1.1542 0.3189 0.055 Uiso 1 1 calc R . .
C12 C 0.2036(3) 1.1077(4) 0.23766(12) 0.0534(9) Uani 1 1 d . . .
H12 H 0.2537 1.1694 0.2169 0.064 Uiso 1 1 calc R . .
C13 C 0.1290(2) 1.0281(4) 0.20737(13) 0.0481(9) Uani 1 1 d . . .
H13 H 0.1273 1.0343 0.1658 0.058 Uiso 1 1 calc R . .
C14 C 0.0560(2) 0.9386(4) 0.23764(11) 0.0426(8) Uani 1 1 d . . .
H14 H 0.0041 0.8831 0.2168 0.051 Uiso 1 1 calc R . .
C15 C 0.0583(2) 0.9297(4) 0.29840(11) 0.0376(7) Uani 1 1 d . . .
H15 H 0.0081 0.8677 0.3189 0.045 Uiso 1 1 calc R . .
N1 N 0.0481(2) 0.5417(4) 0.39492(10) 0.0518(8) Uani 1 1 d . . .
N2 N 0.09984(16) 0.8602(3) 0.42803(9) 0.0326(6) 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
C1 N1 1.148(3) . ?
C1 N2 1.337(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.395(4) . ?
C2 N2 1.413(3) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.438(4) . ?
C8 C9 1.356(4) . ?
C8 H8 0.9500 . ?
C9 N2 1.425(3) . ?
C9 C10 1.465(3) . ?
C10 C11 1.386(4) . ?
C10 C15 1.394(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
N1 C1 N2 177.3(3) . . ?
C3 C2 C7 124.1(3) . . ?
C3 C2 N2 129.0(3) . . ?
C7 C2 N2 106.8(2) . . ?
C2 C3 C4 116.2(3) . . ?
C2 C3 H3 121.9 . . ?
C4 C3 H3 121.9 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 118.1(3) . . ?
C6 C7 C8 134.3(3) . . ?
C2 C7 C8 107.6(2) . . ?
C9 C8 C7 109.4(3) . . ?
C9 C8 H8 125.3 . . ?
C7 C8 H8 125.3 . . ?
C8 C9 N2 107.2(2) . . ?
C8 C9 C10 130.5(3) . . ?
N2 C9 C10 122.3(2) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C9 119.1(3) . . ?
C15 C10 C9 122.4(3) . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C1 N2 C2 122.9(2) . . ?
C1 N2 C9 127.2(2) . . ?
C2 N2 C9 109.0(2) . . ?

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
C7 C2 C3 C4 -0.6(4) . . . . ?
N2 C2 C3 C4 -179.0(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 C2 1.2(4) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
N2 C2 C7 C6 178.6(2) . . . . ?
C3 C2 C7 C8 -179.3(3) . . . . ?
N2 C2 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 -178.7(3) . . . . ?
C2 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 N2 0.1(3) . . . . ?
C7 C8 C9 C10 177.9(3) . . . . ?
C8 C9 C10 C11 34.3(5) . . . . ?
N2 C9 C10 C11 -148.2(3) . . . . ?
C8 C9 C10 C15 -143.9(3) . . . . ?
N2 C9 C10 C15 33.6(4) . . . . ?
C15 C10 C11 C12 0.7(4) . . . . ?
C9 C10 C11 C12 -177.5(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C11 C10 C15 C14 -0.6(4) . . . . ?
C9 C10 C15 C14 177.6(2) . . . . ?
N1 C1 N2 C2 12(7) . . . . ?
N1 C1 N2 C9 180(100) . . . . ?
C3 C2 N2 C1 -10.9(4) . . . . ?
C7 C2 N2 C1 170.5(3) . . . . ?
C3 C2 N2 C9 179.3(3) . . . . ?
C7 C2 N2 C9 0.7(3) . . . . ?
C8 C9 N2 C1 -169.8(3) . . . . ?
C10 C9 N2 C1 12.2(4) . . . . ?
C8 C9 N2 C2 -0.5(3) . . . . ?
C10 C9 N2 C2 -178.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_a17991
_database_code_depnum_ccdc_archive 'CCDC 1511557'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O2 S'
_chemical_formula_sum            'C19 H16 N2 O2 S'
_chemical_formula_weight         336.40

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'

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                   9.3811(4)
_cell_length_b                   20.8484(10)
_cell_length_c                   8.6963(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.098(2)
_cell_angle_gamma                90.00
_cell_volume                     1679.43(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4143
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.19

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9005
_exptl_absorpt_correction_T_max  0.9600
_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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11240
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2958
_reflns_number_gt                2115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0738P)²+0.5980P] 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         2958
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.2001(3) 0.67759(12) 1.1365(3) 0.0636(7) Uani 1 1 d . . .
C2 C 0.2547(4) 0.73632(15) 1.1887(4) 0.0884(9) Uani 1 1 d . . .
H2 H 0.3406 0.7388 1.2584 0.106 Uiso 1 1 calc R . .
C3 C 0.1815(4) 0.79138(14) 1.1372(4) 0.0885(9) Uani 1 1 d . . .
H3 H 0.2189 0.8309 1.1733 0.106 Uiso 1 1 calc R . .
C4 C 0.0552(3) 0.78955(13) 1.0344(3) 0.0703(7) Uani 1 1 d . . .
C5 C -0.0229(4) 0.85033(16) 0.9781(4) 0.0973(10) Uani 1 1 d . . .
H5A H -0.1089 0.8398 0.9072 0.146 Uiso 1 1 calc R . .
H5B H 0.0387 0.8765 0.9258 0.146 Uiso 1 1 calc R . .
H5C H -0.0483 0.8734 1.0654 0.146 Uiso 1 1 calc R . .
C6 C 0.0029(3) 0.73018(16) 0.9856(4) 0.0904(10) Uani 1 1 d . . .
H6 H -0.0832 0.7277 0.9163 0.108 Uiso 1 1 calc R . .
C7 C 0.0734(3) 0.67435(14) 1.0354(4) 0.0835(9) Uani 1 1 d . . .
H7 H 0.0351 0.6348 1.0005 0.100 Uiso 1 1 calc R . .
C8 C 0.3163(3) 0.55701(11) 0.9156(3) 0.0614(7) Uani 1 1 d . . .
C9 C 0.1814(3) 0.52953(14) 0.8741(4) 0.0776(8) Uani 1 1 d . . .
H9 H 0.1158 0.5278 0.9438 0.093 Uiso 1 1 calc R . .
C10 C 0.1479(4) 0.50503(15) 0.7268(5) 0.0905(10) Uani 1 1 d . . .
H10 H 0.0575 0.4867 0.6964 0.109 Uiso 1 1 calc R . .
C11 C 0.2449(4) 0.50671(15) 0.6214(4) 0.0889(9) Uani 1 1 d . . .
H11 H 0.2184 0.4898 0.5220 0.107 Uiso 1 1 calc R . .
C12 C 0.3788(4) 0.53308(14) 0.6630(4) 0.0784(8) Uani 1 1 d . . .
H12 H 0.4441 0.5341 0.5929 0.094 Uiso 1 1 calc R . .
C13 C 0.4159(3) 0.55833(11) 0.8119(3) 0.0617(7) Uani 1 1 d . . .
C14 C 0.5429(3) 0.58897(12) 0.8910(3) 0.0634(7) Uani 1 1 d . . .
C15 C 0.6733(4) 0.59899(15) 0.8308(4) 0.0838(9) Uani 1 1 d . . .
C16 C 0.5233(3) 0.60644(12) 1.0365(3) 0.0658(7) Uani 1 1 d . . .
C17 C 0.6328(4) 0.63916(17) 1.1555(4) 0.0917(9) Uani 1 1 d . . .
H17A H 0.6138 0.6273 1.2583 0.110 Uiso 1 1 calc R . .
H17B H 0.7276 0.6228 1.1453 0.110 Uiso 1 1 calc R . .
C18 C 0.6367(4) 0.7099(2) 1.1461(5) 0.1079(12) Uani 1 1 d . . .
H18 H 0.6952 0.7297 1.2289 0.129 Uiso 1 1 calc R . .
C19 C 0.5768(6) 0.7460(2) 1.0493(6) 0.1363(16) Uani 1 1 d . . .
H19A H 0.5164 0.7299 0.9628 0.164 Uiso 1 1 calc R . .
H19B H 0.5909 0.7900 1.0608 0.164 Uiso 1 1 calc R . .
N1 N 0.3836(2) 0.58652(10) 1.0553(2) 0.0660(6) Uani 1 1 d . . .
N2 N 0.7768(4) 0.60715(16) 0.7822(4) 0.1233(12) Uani 1 1 d . . .
O1 O 0.4006(3) 0.62188(12) 1.3329(2) 0.1072(8) Uani 1 1 d . . .
O2 O 0.1931(3) 0.55739(10) 1.2085(3) 0.1073(8) Uani 1 1 d . . .
S1 S 0.29337(9) 0.60753(4) 1.20158(9) 0.0806(3) 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
C1 C7 1.364(4) . ?
C1 C2 1.376(4) . ?
C1 S1 1.750(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.374(4) . ?
C4 C5 1.507(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.384(4) . ?
C8 C13 1.397(3) . ?
C8 N1 1.418(3) . ?
C9 C10 1.368(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.429(4) . ?
C14 C16 1.357(4) . ?
C14 C15 1.421(4) . ?
C15 N2 1.131(4) . ?
C16 N1 1.409(3) . ?
C16 C17 1.502(4) . ?
C17 C18 1.478(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.200(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
N1 S1 1.693(2) . ?
O1 S1 1.429(2) . ?
O2 S1 1.414(2) . ?

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
C7 C1 C2 119.8(3) . . ?
C7 C1 S1 120.5(2) . . ?
C2 C1 S1 119.7(2) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C6 117.2(3) . . ?
C3 C4 C5 121.1(3) . . ?
C6 C4 C5 121.7(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 122.4(3) . . ?
C7 C6 H6 118.8 . . ?
C4 C6 H6 118.8 . . ?
C1 C7 C6 119.2(3) . . ?
C1 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C13 121.1(3) . . ?
C9 C8 N1 131.9(2) . . ?
C13 C8 N1 107.0(2) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 122.1(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 119.9(3) . . ?
C12 C13 C14 133.2(3) . . ?
C8 C13 C14 106.8(2) . . ?
C16 C14 C15 123.8(3) . . ?
C16 C14 C13 110.1(2) . . ?
C15 C14 C13 126.1(3) . . ?
N2 C15 C14 179.7(4) . . ?
C14 C16 N1 107.1(3) . . ?
C14 C16 C17 125.9(3) . . ?
N1 C16 C17 127.0(3) . . ?
C18 C17 C16 115.8(3) . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 130.6(4) . . ?
C19 C18 H18 114.7 . . ?
C17 C18 H18 114.7 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C16 N1 C8 108.9(2) . . ?
C16 N1 S1 126.6(2) . . ?
C8 N1 S1 123.25(18) . . ?
O2 S1 O1 120.66(15) . . ?
O2 S1 N1 104.81(13) . . ?
O1 S1 N1 106.39(14) . . ?
O2 S1 C1 109.19(14) . . ?
O1 S1 C1 109.66(14) . . ?
N1 S1 C1 104.88(11) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_a15781
_database_code_depnum_ccdc_archive 'CCDC 1511558'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O2 S'
_chemical_formula_sum            'C16 H12 N2 O2 S'
_chemical_formula_weight         296.34

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'

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                   9.0829(15)
_cell_length_b                   10.2351(14)
_cell_length_c                   15.664(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.384(10)
_cell_angle_gamma                90.00
_cell_volume                     1444.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    808
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      22.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9492
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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 APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9899
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0839
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2547
_reflns_number_gt                1556
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0491P)²+0.2463P] 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         2547
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_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
C1 C 0.3412(3) 0.1652(3) 0.1185(2) 0.0309(8) Uani 1 1 d . . .
C2 C 0.4047(4) 0.0408(3) 0.1177(2) 0.0409(9) Uani 1 1 d . . .
H2 H 0.4831 0.0162 0.1608 0.049 Uiso 1 1 calc R . .
C3 C 0.3516(4) -0.0459(3) 0.0534(2) 0.0488(10) Uani 1 1 d . . .
H3 H 0.3942 -0.1306 0.0530 0.059 Uiso 1 1 calc R . .
C4 C 0.2373(4) -0.0122(3) -0.0108(2) 0.0403(9) Uani 1 1 d . . .
C5 C 0.1822(4) -0.1052(4) -0.0832(3) 0.0600(12) Uani 1 1 d . . .
H5A H 0.1019 -0.0636 -0.1215 0.090 Uiso 1 1 calc R . .
H5B H 0.1451 -0.1852 -0.0590 0.090 Uiso 1 1 calc R . .
H5C H 0.2640 -0.1269 -0.1158 0.090 Uiso 1 1 calc R . .
C6 C 0.1744(4) 0.1120(3) -0.0082(2) 0.0416(9) Uani 1 1 d . . .
H6 H 0.0950 0.1361 -0.0509 0.050 Uiso 1 1 calc R . .
C7 C 0.2260(4) 0.2008(3) 0.0557(2) 0.0385(9) Uani 1 1 d . . .
H7 H 0.1829 0.2853 0.0564 0.046 Uiso 1 1 calc R . .
C8 C 0.1717(3) 0.2233(3) 0.2932(2) 0.0293(8) Uani 1 1 d . . .
C9 C 0.0604(4) 0.3057(3) 0.2540(2) 0.0348(9) Uani 1 1 d . . .
H9 H 0.0804 0.3702 0.2135 0.042 Uiso 1 1 calc R . .
C10 C -0.0799(4) 0.2891(4) 0.2770(2) 0.0430(10) Uani 1 1 d . . .
H10 H -0.1583 0.3431 0.2512 0.052 Uiso 1 1 calc R . .
C11 C -0.1103(4) 0.1951(3) 0.3373(2) 0.0439(10) Uani 1 1 d . . .
H11 H -0.2086 0.1862 0.3511 0.053 Uiso 1 1 calc R . .
C12 C 0.0006(4) 0.1152(3) 0.3768(2) 0.0376(9) Uani 1 1 d . . .
H12 H -0.0198 0.0523 0.4183 0.045 Uiso 1 1 calc R . .
C13 C 0.1437(3) 0.1292(3) 0.3541(2) 0.0294(8) Uani 1 1 d . . .
C14 C 0.2853(4) 0.0676(3) 0.3832(2) 0.0307(8) Uani 1 1 d . . .
C15 C 0.3899(4) 0.1223(3) 0.3401(2) 0.0341(8) Uani 1 1 d . . .
H15 H 0.4916 0.0978 0.3461 0.041 Uiso 1 1 calc R . .
C16 C 0.3119(4) -0.0298(3) 0.4498(2) 0.0378(9) Uani 1 1 d . . .
N1 N 0.3255(3) 0.2196(2) 0.28589(16) 0.0312(7) Uani 1 1 d . . .
N2 N 0.3305(3) -0.1058(3) 0.5036(2) 0.0569(10) Uani 1 1 d . . .
O1 O 0.3419(2) 0.40154(19) 0.18142(15) 0.0415(6) Uani 1 1 d . . .
O2 O 0.5603(2) 0.2584(2) 0.22601(15) 0.0453(7) Uani 1 1 d . . .
S1 S 0.40429(9) 0.27468(8) 0.20094(6) 0.0341(3) 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
C1 C7 1.390(4) . ?
C1 C2 1.398(4) . ?
C1 S1 1.751(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(5) . ?
C3 H3 0.9500 . ?
C4 C6 1.396(4) . ?
C4 C5 1.516(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C8 C13 1.402(4) . ?
C8 N1 1.417(4) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.452(4) . ?
C14 C15 1.355(4) . ?
C14 C16 1.441(4) . ?
C15 N1 1.389(4) . ?
C15 H15 0.9500 . ?
C16 N2 1.143(4) . ?
N1 S1 1.687(3) . ?
O1 S1 1.434(2) . ?
O2 S1 1.431(2) . ?

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
C7 C1 C2 120.5(3) . . ?
C7 C1 S1 120.0(3) . . ?
C2 C1 S1 119.5(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C6 118.4(3) . . ?
C3 C4 C5 121.9(3) . . ?
C6 C4 C5 119.8(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C4 C6 H6 119.5 . . ?
C6 C7 C1 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C1 C7 H7 120.2 . . ?
C9 C8 C13 122.0(3) . . ?
C9 C8 N1 130.3(3) . . ?
C13 C8 N1 107.6(3) . . ?
C10 C9 C8 116.9(3) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 C14 133.7(3) . . ?
C8 C13 C14 106.3(3) . . ?
C15 C14 C16 125.7(3) . . ?
C15 C14 C13 108.3(3) . . ?
C16 C14 C13 126.0(3) . . ?
C14 C15 N1 109.5(3) . . ?
C14 C15 H15 125.3 . . ?
N1 C15 H15 125.3 . . ?
N2 C16 C14 178.4(4) . . ?
C15 N1 C8 108.2(3) . . ?
C15 N1 S1 122.3(2) . . ?
C8 N1 S1 125.3(2) . . ?
O2 S1 O1 120.96(13) . . ?
O2 S1 N1 104.49(13) . . ?
O1 S1 N1 105.95(14) . . ?
O2 S1 C1 110.28(15) . . ?
O1 S1 C1 109.86(15) . . ?
N1 S1 C1 103.67(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.057

