# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1555302'
_audit_update_record             
;
2017-06-10 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2 S'
_chemical_formula_weight         300.37

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'
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   P2(1)/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                   16.315(5)
_cell_length_b                   12.408(4)
_cell_length_c                   7.380(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.840(5)
_cell_angle_gamma                90.00
_cell_volume                     1488.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    52
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_process_details   SADABS

_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
_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            9422
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3087
_reflns_number_gt                2290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0770P)²+0.1876P] 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         3087
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.21256(11) 0.88273(15) 0.3230(2) 0.0388(4) Uani 1 1 d . . .
C2 C 0.24775(13) 0.78107(16) 0.3234(3) 0.0474(5) Uani 1 1 d . . .
H2 H 0.3034 0.7730 0.3079 0.057 Uiso 1 1 calc R . .
C3 C 0.19920(15) 0.69174(18) 0.3472(3) 0.0557(6) Uani 1 1 d . . .
H3 H 0.2226 0.6234 0.3491 0.067 Uiso 1 1 calc R . .
C4 C 0.11714(15) 0.70279(19) 0.3679(3) 0.0578(6) Uani 1 1 d . . .
H4 H 0.0856 0.6421 0.3870 0.069 Uiso 1 1 calc R . .
C5 C 0.08083(13) 0.8030(2) 0.3608(3) 0.0534(6) Uani 1 1 d . . .
H5 H 0.0247 0.8099 0.3717 0.064 Uiso 1 1 calc R . .
C6 C 0.12884(12) 0.89410(17) 0.3371(3) 0.0430(5) Uani 1 1 d . . .
C7 C 0.14379(11) 1.06770(16) 0.1352(3) 0.0419(5) Uani 1 1 d . . .
C8 C 0.10884(14) 1.12376(18) -0.0152(3) 0.0542(5) Uani 1 1 d . . .
H8 H 0.0529 1.1395 -0.0249 0.065 Uiso 1 1 calc R . .
C9 C 0.15717(15) 1.15595(19) -0.1499(3) 0.0618(6) Uani 1 1 d . . .
H9 H 0.1339 1.1951 -0.2487 0.074 Uiso 1 1 calc R . .
C10 C 0.23964(15) 1.13061(17) -0.1392(3) 0.0547(6) Uani 1 1 d . . .
H10 H 0.2718 1.1523 -0.2309 0.066 Uiso 1 1 calc R . .
C11 C 0.27452(13) 1.07304(16) 0.0077(3) 0.0461(5) Uani 1 1 d . . .
H11 H 0.3299 1.0542 0.0132 0.055 Uiso 1 1 calc R . .
C12 C 0.22714(11) 1.04312(14) 0.1472(3) 0.0387(4) Uani 1 1 d . . .
C13 C 0.32377(11) 1.01252(15) 0.4178(3) 0.0380(4) Uani 1 1 d . . .
C14 C 0.35749(12) 1.11545(17) 0.4051(3) 0.0463(5) Uani 1 1 d . . .
H14 H 0.3372 1.1611 0.3119 0.056 Uiso 1 1 calc R . .
C15 C 0.41975(12) 1.15056(18) 0.5270(3) 0.0500(5) Uani 1 1 d . . .
H15 H 0.4409 1.2197 0.5162 0.060 Uiso 1 1 calc R . .
C16 C 0.45173(12) 1.08327(18) 0.6674(3) 0.0459(5) Uani 1 1 d . . .
C17 C 0.41864(12) 0.98143(18) 0.6816(3) 0.0478(5) Uani 1 1 d . . .
H17 H 0.4393 0.9359 0.7747 0.057 Uiso 1 1 calc R . .
C18 C 0.35569(12) 0.94627(17) 0.5605(3) 0.0453(5) Uani 1 1 d . . .
H18 H 0.3340 0.8777 0.5735 0.054 Uiso 1 1 calc R . .
C19 C 0.51716(13) 1.12005(19) 0.7947(3) 0.0534(5) Uani 1 1 d . . .
N1 N 0.25960(9) 0.97830(12) 0.2960(2) 0.0411(4) Uani 1 1 d . . .
N2 N 0.56869(13) 1.15007(19) 0.8971(3) 0.0697(6) Uani 1 1 d . . .
S1 S 0.08417(3) 1.02320(5) 0.31080(8) 0.0547(2) 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 C6 1.386(3) . ?
C1 C2 1.386(3) . ?
C1 N1 1.436(2) . ?
C2 C3 1.382(3) . ?
C3 C4 1.367(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.395(3) . ?
C6 S1 1.764(2) . ?
C7 C12 1.389(3) . ?
C7 C8 1.390(3) . ?
C7 S1 1.773(2) . ?
C8 C9 1.379(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.389(3) . ?
C12 N1 1.427(2) . ?
C13 N1 1.387(2) . ?
C13 C14 1.397(3) . ?
C13 C18 1.402(3) . ?
C14 C15 1.370(3) . ?
C15 C16 1.397(3) . ?
C16 C17 1.382(3) . ?
C16 C19 1.436(3) . ?
C17 C18 1.374(3) . ?
C19 N2 1.144(3) . ?

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
C6 C1 C2 120.21(17) . . ?
C6 C1 N1 117.92(16) . . ?
C2 C1 N1 121.73(17) . . ?
C3 C2 C1 119.24(19) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 120.6(2) . . ?
C4 C5 C6 119.5(2) . . ?
C1 C6 C5 119.63(19) . . ?
C1 C6 S1 119.01(15) . . ?
C5 C6 S1 121.25(16) . . ?
C12 C7 C8 119.63(18) . . ?
C12 C7 S1 118.64(14) . . ?
C8 C7 S1 121.71(16) . . ?
C9 C8 C7 119.9(2) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C11 119.9(2) . . ?
C10 C11 C12 120.13(19) . . ?
C7 C12 C11 119.79(18) . . ?
C7 C12 N1 118.10(17) . . ?
C11 C12 N1 121.84(17) . . ?
N1 C13 C14 121.10(17) . . ?
N1 C13 C18 121.30(17) . . ?
C14 C13 C18 117.58(18) . . ?
C15 C14 C13 121.42(19) . . ?
C14 C15 C16 120.5(2) . . ?
C17 C16 C15 118.64(18) . . ?
C17 C16 C19 120.98(19) . . ?
C15 C16 C19 120.4(2) . . ?
C18 C17 C16 121.07(18) . . ?
C17 C18 C13 120.83(19) . . ?
N2 C19 C16 179.2(3) . . ?
C13 N1 C12 122.47(15) . . ?
C13 N1 C1 123.09(15) . . ?
C12 N1 C1 113.86(14) . . ?
C6 S1 C7 96.66(9) . . ?

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 -3.2(3) . . . . ?
N1 C1 C2 C3 -178.97(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C2 C1 C6 C5 3.2(3) . . . . ?
N1 C1 C6 C5 179.09(17) . . . . ?
C2 C1 C6 S1 -173.02(15) . . . . ?
N1 C1 C6 S1 2.9(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 S1 175.42(17) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
S1 C7 C8 C9 -179.28(17) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
S1 C7 C12 C11 177.27(15) . . . . ?
C8 C7 C12 N1 -175.17(18) . . . . ?
S1 C7 C12 N1 3.2(2) . . . . ?
C10 C11 C12 C7 2.5(3) . . . . ?
C10 C11 C12 N1 176.30(18) . . . . ?
N1 C13 C14 C15 178.69(19) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C14 C15 C16 C19 179.8(2) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C19 C16 C17 C18 179.64(19) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
N1 C13 C18 C17 -179.25(18) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C17 C16 C19 N2 -103(21) . . . . ?
C15 C16 C19 N2 76(21) . . . . ?
C14 C13 N1 C12 3.1(3) . . . . ?
C18 C13 N1 C12 -178.61(17) . . . . ?
C14 C13 N1 C1 -167.63(18) . . . . ?
C18 C13 N1 C1 10.7(3) . . . . ?
C7 C12 N1 C13 -122.7(2) . . . . ?
C11 C12 N1 C13 63.3(3) . . . . ?
C7 C12 N1 C1 48.7(2) . . . . ?
C11 C12 N1 C1 -125.19(19) . . . . ?
C6 C1 N1 C13 119.0(2) . . . . ?
C2 C1 N1 C13 -65.1(3) . . . . ?
C6 C1 N1 C12 -52.4(2) . . . . ?
C2 C1 N1 C12 123.5(2) . . . . ?
C1 C6 S1 C7 38.01(17) . . . . ?
C5 C6 S1 C7 -138.14(17) . . . . ?
C12 C7 S1 C6 -41.26(17) . . . . ?
C8 C7 S1 C6 137.10(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_mo_161226d_0m
_database_code_depnum_ccdc_archive 'CCDC 1555301'
_audit_update_record             
;
2017-06-10 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2017-01-11
_chemical_formula_sum            'C19 H12 N2 S'
_chemical_formula_weight         300.370
_refine_ls_R_factor_all          0.044
_cell_length_a                   10.3472(10)
_cell_length_b                   12.6805(12)
_cell_length_c                   12.7346(12)
_cell_angle_alpha                91.281(1)
_cell_angle_beta                 109.390(1)
_cell_angle_gamma                111.059(1)
_cell_volume                     1451.7(2)
_cell_formula_units_Z            4
_exptl_crystal_density_meas      0.000
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
S ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C 0.3187(2) 0.1054(1) 0.6573(1) 1.000 2 i ? d Uani 0.0160(2)
C2 C 0.1797(2) 0.0520(1) 0.6678(1) 1.000 2 i ? d Uani 0.0190(3)
H2 H 0.1275 0.0970 0.6785 1.000 2 i ? calc Uiso 0.02300
C3 C 0.1183(2) -0.0653(1) 0.6627(1) 1.000 2 i ? d Uani 0.0197(3)
H3 H 0.0242 -0.1004 0.6697 1.000 2 i ? calc Uiso 0.02400
C4 C 0.1941(2) -0.1330(1) 0.6472(1) 1.000 2 i ? d Uani 0.0176(3)
C5 C 0.3308(2) -0.0808(1) 0.6349(1) 1.000 2 i ? d Uani 0.0184(3)
H5 H 0.3824 -0.1261 0.6238 1.000 2 i ? calc Uiso 0.02200
C6 C 0.3921(2) 0.0364(1) 0.6389(1) 1.000 2 i ? d Uani 0.0183(3)
H6 H 0.4846 0.0708 0.6291 1.000 2 i ? calc Uiso 0.02200
C7 C 0.1324(2) -0.2547(1) 0.6449(1) 1.000 2 i ? d Uani 0.0189(3)
C8 C 0.3076(2) 0.2919(1) 0.6914(1) 1.000 2 i ? d Uani 0.0159(2)
C9 C 0.3065(2) 0.3082(1) 0.7997(1) 1.000 2 i ? d Uani 0.0183(3)
H9 H 0.3589 0.2774 0.8585 1.000 2 i ? calc Uiso 0.02200
C10 C 0.2280(2) 0.3698(1) 0.8212(1) 1.000 2 i ? d Uani 0.0199(3)
H10 H 0.2259 0.3801 0.8947 1.000 2 i ? calc Uiso 0.02400
C11 C 0.1528(2) 0.4162(1) 0.7360(1) 1.000 2 i ? d Uani 0.0191(3)
H11 H 0.0984 0.4573 0.7511 1.000 2 i ? calc Uiso 0.02300
C12 C 0.1569(2) 0.4029(1) 0.6285(1) 1.000 2 i ? d Uani 0.0177(3)
H12 H 0.1070 0.4359 0.5705 1.000 2 i ? calc Uiso 0.02100
C13 C 0.2350(2) 0.3406(1) 0.6065(1) 1.000 2 i ? d Uani 0.0159(2)
C14 C 0.4250(2) 0.3249(1) 0.5126(1) 1.000 2 i ? d Uani 0.0166(3)
C15 C 0.5128(2) 0.3715(1) 0.4496(1) 1.000 2 i ? d Uani 0.0206(3)
H15 H 0.4778 0.4065 0.3870 1.000 2 i ? calc Uiso 0.02500
C16 C 0.6523(2) 0.3665(1) 0.4791(1) 1.000 2 i ? d Uani 0.0243(3)
H16 H 0.7099 0.3935 0.4334 1.000 2 i ? calc Uiso 0.02900
C17 C 0.7077(2) 0.3223(1) 0.5744(1) 1.000 2 i ? d Uani 0.0244(3)
H17 H 0.8045 0.3216 0.5953 1.000 2 i ? calc Uiso 0.02900
C18 C 0.6222(2) 0.2790(1) 0.6398(1) 1.000 2 i ? d Uani 0.0212(3)
H18 H 0.6618 0.2515 0.7069 1.000 2 i ? calc Uiso 0.02500
C19 C 0.4783(2) 0.2760(1) 0.6065(1) 1.000 2 i ? d Uani 0.0167(3)
C20 C 0.2995(2) 0.2810(1) 0.1559(1) 1.000 2 i ? d Uani 0.0148(2)
C21 C 0.3733(2) 0.3889(1) 0.1323(1) 1.000 2 i ? d Uani 0.0197(3)
H21 H 0.4635 0.4046 0.1199 1.000 2 i ? calc Uiso 0.02400
C22 C 0.3161(2) 0.4731(1) 0.1270(1) 1.000 2 i ? d Uani 0.0202(3)
H22 H 0.3676 0.5458 0.1112 1.000 2 i ? calc Uiso 0.02400
C23 C 0.1840(2) 0.4517(1) 0.1448(1) 1.000 2 i ? d Uani 0.0184(3)
C24 C 0.1113(2) 0.3455(1) 0.1702(1) 1.000 2 i ? d Uani 0.0204(3)
H24 H 0.0220 0.3306 0.1838 1.000 2 i ? calc Uiso 0.02400
C25 C 0.1681(2) 0.2612(1) 0.1759(1) 1.000 2 i ? d Uani 0.0180(3)
H25 H 0.1174 0.1892 0.1935 1.000 2 i ? calc Uiso 0.02200
C26 C 0.1215(2) 0.5376(1) 0.1327(1) 1.000 2 i ? d Uani 0.0208(3)
C27 C 0.4434(2) 0.1912(1) 0.0950(1) 1.000 2 i ? d Uani 0.0172(3)
C28 C 0.5890(2) 0.2703(1) 0.1237(1) 1.000 2 i ? d Uani 0.0218(3)
H28 H 0.6345 0.3253 0.1904 1.000 2 i ? calc Uiso 0.02600
C29 C 0.6672(2) 0.2684(1) 0.0541(1) 1.000 2 i ? d Uani 0.0266(3)
H29 H 0.7643 0.3251 0.0711 1.000 2 i ? calc Uiso 0.03200
C30 C 0.6045(2) 0.1842(2) -0.0401(1) 1.000 2 i ? d Uani 0.0270(3)
H30 H 0.6584 0.1841 -0.0877 1.000 2 i ? calc Uiso 0.03200
C31 C 0.4636(2) 0.1005(1) -0.0650(1) 1.000 2 i ? d Uani 0.0227(3)
H31 H 0.4233 0.0400 -0.1265 1.000 2 i ? calc Uiso 0.02700
C32 C 0.3810(2) 0.1056(1) 0.0010(1) 1.000 2 i ? d Uani 0.0179(3)
C33 C 0.1984(2) -0.0095(1) 0.1034(1) 1.000 2 i ? d Uani 0.0167(3)
C34 C 0.1214(2) -0.1151(1) 0.1283(1) 1.000 2 i ? d Uani 0.0197(3)
H34 H 0.0680 -0.1806 0.0709 1.000 2 i ? calc Uiso 0.02400
C35 C 0.1233(2) -0.1241(1) 0.2372(1) 1.000 2 i ? d Uani 0.0211(3)
H35 H 0.0690 -0.1954 0.2540 1.000 2 i ? calc Uiso 0.02500
C36 C 0.2046(2) -0.0289(1) 0.3219(1) 1.000 2 i ? d Uani 0.0210(3)
H36 H 0.2060 -0.0354 0.3964 1.000 2 i ? calc Uiso 0.02500
C37 C 0.2838(2) 0.0759(1) 0.2975(1) 1.000 2 i ? d Uani 0.0191(3)
H37 H 0.3414 0.1404 0.3558 1.000 2 i ? calc Uiso 0.02300
C38 C 0.2785(2) 0.0862(1) 0.1877(1) 1.000 2 i ? d Uani 0.0161(2)
N1 N 0.3832(1) 0.2249(1) 0.6670(1) 1.000 2 i ? d Uani 0.0169(2)
N2 N 0.0850(2) -0.3521(1) 0.6433(1) 1.000 2 i ? d Uani 0.0237(3)
N3 N 0.3560(1) 0.1945(1) 0.1610(1) 1.000 2 i ? d Uani 0.0168(2)
N4 N 0.0716(2) 0.6061(1) 0.1211(1) 1.000 2 i ? d Uani 0.0266(3)
S1 S 0.2442(0) 0.3247(0) 0.4712(0) 1.000 2 i ? d Uani 0.01791(9)
S2 S 0.1975(0) 0.0041(0) -0.0345(0) 1.000 2 i ? d Uani 0.02016(9)
Dummy ? 0.5248 1.1867 1.0281 ? 2 i ? d ? ?



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . . 1.4024(16) no
C1 C2 . . 1.406(2) no
C1 C6 . . 1.4084(18) no
C2 C3 . . 1.3826(19) no
C2 H2 . . 0.9500 no
C3 C4 . . 1.4029(18) no
C3 H3 . . 0.9500 no
C4 C5 . . 1.393(2) no
C4 C7 . . 1.4380(19) no
C5 C6 . . 1.3829(19) no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C7 N2 . . 1.1511(19) no
C8 C13 . . 1.3920(19) no
C8 C9 . . 1.3950(18) no
C8 N1 . . 1.4345(16) no
C9 C10 . . 1.3915(19) no
C9 H9 . . 0.9500 no
C10 C11 . . 1.388(2) no
C10 H10 . . 0.9500 no
C11 C12 . . 1.3925(19) no
C11 H11 . . 0.9500 no
C12 C13 . . 1.3981(18) no
C12 H12 . . 0.9500 no
C13 S1 . . 1.7680(13) no
C14 C15 . . 1.3920(19) no
C14 C19 . . 1.399(2) no
C14 S1 . . 1.7658(14) no
C15 C16 . . 1.392(2) no
C15 H15 . . 0.9500 no
C16 C17 . . 1.384(2) no
C16 H16 . . 0.9500 no
C17 C18 . . 1.393(2) no
C17 H17 . . 0.9500 no
C18 C19 . . 1.392(2) no
C18 H18 . . 0.9500 no
C19 N1 . . 1.4318(17) no
C20 C25 . . 1.4014(19) no
C20 C21 . . 1.4025(18) no
C20 N3 . . 1.4095(16) no
C21 C22 . . 1.3866(19) no
C21 H21 . . 0.9500 no
C22 C23 . . 1.391(2) no
C22 H22 . . 0.9500 no
C23 C24 . . 1.392(2) no
C23 C26 . . 1.4408(19) no
C24 C25 . . 1.3851(19) no
C24 H24 . . 0.9500 no
C25 H25 . . 0.9500 no
C26 N4 . . 1.1481(19) no
C27 C28 . . 1.393(2) no
C27 C32 . . 1.3978(19) no
C27 N3 . . 1.4343(16) no
C28 C29 . . 1.390(2) no
C28 H28 . . 0.9500 no
C29 C30 . . 1.388(2) no
C29 H29 . . 0.9500 no
C30 C31 . . 1.386(2) no
C30 H30 . . 0.9500 no
C31 C32 . . 1.3978(19) no
C31 H31 . . 0.9500 no
C32 S2 . . 1.7639(15) no
C33 C38 . . 1.3926(18) no
C33 C34 . . 1.3960(19) no
C33 S2 . . 1.7655(14) no
C34 C35 . . 1.389(2) no
C34 H34 . . 0.9500 no
C35 C36 . . 1.392(2) no
C35 H35 . . 0.9500 no
C36 C37 . . 1.3926(19) no
C36 H36 . . 0.9500 no
C37 C38 . . 1.3918(19) no
C37 H37 . . 0.9500 no
C38 N3 . . 1.4334(17) no
Dummy Dummy . 2_677 4.5886(4) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . . 120.34(11) no
N1 C1 C6 . . . 121.11(12) no
C2 C1 C6 . . . 118.55(12) no
C3 C2 C1 . . . 120.56(12) no
C3 C2 H2 . . . 119.70 no
C1 C2 H2 . . . 119.70 no
C2 C3 C4 . . . 120.44(13) no
C2 C3 H3 . . . 119.80 no
C4 C3 H3 . . . 119.80 no
C5 C4 C3 . . . 119.25(12) no
C5 C4 C7 . . . 120.19(12) no
C3 C4 C7 . . . 120.56(13) no
C6 C5 C4 . . . 120.59(12) no
C6 C5 H5 . . . 119.70 no
C4 C5 H5 . . . 119.70 no
C5 C6 C1 . . . 120.57(13) no
C5 C6 H6 . . . 119.70 no
C1 C6 H6 . . . 119.70 no
N2 C7 C4 . . . 179.05(15) no
C13 C8 C9 . . . 120.03(12) no
C13 C8 N1 . . . 119.76(12) no
C9 C8 N1 . . . 120.21(12) no
C10 C9 C8 . . . 119.59(13) no
C10 C9 H9 . . . 120.20 no
C8 C9 H9 . . . 120.20 no
C11 C10 C9 . . . 120.44(13) no
C11 C10 H10 . . . 119.80 no
C9 C10 H10 . . . 119.80 no
C10 C11 C12 . . . 120.21(12) no
C10 C11 H11 . . . 119.90 no
C12 C11 H11 . . . 119.90 no
C11 C12 C13 . . . 119.48(13) no
C11 C12 H12 . . . 120.30 no
C13 C12 H12 . . . 120.30 no
C8 C13 C12 . . . 120.21(12) no
C8 C13 S1 . . . 119.56(10) no
C12 C13 S1 . . . 120.23(11) no
C15 C14 C19 . . . 120.22(13) no
C15 C14 S1 . . . 119.54(11) no
C19 C14 S1 . . . 120.22(10) no
C16 C15 C14 . . . 119.43(14) no
C16 C15 H15 . . . 120.30 no
C14 C15 H15 . . . 120.30 no
C17 C16 C15 . . . 120.45(14) no
C17 C16 H16 . . . 119.80 no
C15 C16 H16 . . . 119.80 no
C16 C17 C18 . . . 120.22(14) no
C16 C17 H17 . . . 119.90 no
C18 C17 H17 . . . 119.90 no
C19 C18 C17 . . . 119.70(14) no
C19 C18 H18 . . . 120.10 no
C17 C18 H18 . . . 120.10 no
C18 C19 C14 . . . 119.73(13) no
C18 C19 N1 . . . 121.39(13) no
C14 C19 N1 . . . 118.87(12) no
C25 C20 C21 . . . 118.20(12) no
C25 C20 N3 . . . 120.41(12) no
C21 C20 N3 . . . 121.39(12) no
C22 C21 C20 . . . 120.76(13) no
C22 C21 H21 . . . 119.60 no
C20 C21 H21 . . . 119.60 no
C21 C22 C23 . . . 120.52(13) no
C21 C22 H22 . . . 119.70 no
C23 C22 H22 . . . 119.70 no
C22 C23 C24 . . . 119.15(12) no
C22 C23 C26 . . . 119.90(13) no
C24 C23 C26 . . . 120.91(13) no
C25 C24 C23 . . . 120.56(13) no
C25 C24 H24 . . . 119.70 no
C23 C24 H24 . . . 119.70 no
C24 C25 C20 . . . 120.79(13) no
C24 C25 H25 . . . 119.60 no
C20 C25 H25 . . . 119.60 no
N4 C26 C23 . . . 178.70(16) no
C28 C27 C32 . . . 119.74(13) no
C28 C27 N3 . . . 121.40(12) no
C32 C27 N3 . . . 118.85(12) no
C29 C28 C27 . . . 119.67(14) no
C29 C28 H28 . . . 120.20 no
C27 C28 H28 . . . 120.20 no
C30 C29 C28 . . . 120.44(15) no
C30 C29 H29 . . . 119.80 no
C28 C29 H29 . . . 119.80 no
C31 C30 C29 . . . 120.22(14) no
C31 C30 H30 . . . 119.90 no
C29 C30 H30 . . . 119.90 no
C30 C31 C32 . . . 119.59(14) no
C30 C31 H31 . . . 120.20 no
C32 C31 H31 . . . 120.20 no
C27 C32 C31 . . . 120.08(14) no
C27 C32 S2 . . . 119.89(10) no
C31 C32 S2 . . . 120.04(11) no
C38 C33 C34 . . . 120.23(13) no
C38 C33 S2 . . . 119.24(10) no
C34 C33 S2 . . . 120.52(10) no
C35 C34 C33 . . . 119.69(13) no
C35 C34 H34 . . . 120.20 no
C33 C34 H34 . . . 120.20 no
C34 C35 C36 . . . 120.14(13) no
C34 C35 H35 . . . 119.90 no
C36 C35 H35 . . . 119.90 no
C35 C36 C37 . . . 120.13(13) no
C35 C36 H36 . . . 119.90 no
C37 C36 H36 . . . 119.90 no
C38 C37 C36 . . . 119.91(13) no
C38 C37 H37 . . . 120.00 no
C36 C37 H37 . . . 120.00 no
C37 C38 C33 . . . 119.85(12) no
C37 C38 N3 . . . 120.40(12) no
C33 C38 N3 . . . 119.75(12) no
C1 N1 C19 . . . 120.1(1) no
C1 N1 C8 . . . 119.08(11) no
C19 N1 C8 . . . 114.99(11) no
C20 N3 C38 . . . 119.48(11) no
C20 N3 C27 . . . 119.89(11) no
C38 N3 C27 . . . 115.07(10) no
C14 S1 C13 . . . 98.51(6) no
C32 S2 C33 . . . 98.39(6) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -177.47(13) no
C6 C1 C2 C3 . . . . 1.4(2) no
C1 C2 C3 C4 . . . . 0.2(2) no
C2 C3 C4 C5 . . . . -1.2(2) no
C2 C3 C4 C7 . . . . 178.33(13) no
C3 C4 C5 C6 . . . . 0.6(2) no
C7 C4 C5 C6 . . . . -178.96(13) no
C4 C5 C6 C1 . . . . 1.1(2) no
N1 C1 C6 C5 . . . . 176.83(13) no
C2 C1 C6 C5 . . . . -2.1(2) no
C5 C4 C7 N2 . . . . 19.(9) no
C3 C4 C7 N2 . . . . -161.(9) no
C13 C8 C9 C10 . . . . 2.2(2) no
N1 C8 C9 C10 . . . . -177.56(12) no
C8 C9 C10 C11 . . . . -0.9(2) no
C9 C10 C11 C12 . . . . -0.8(2) no
C10 C11 C12 C13 . . . . 1.2(2) no
C9 C8 C13 C12 . . . . -1.9(2) no
N1 C8 C13 C12 . . . . 177.87(12) no
C9 C8 C13 S1 . . . . 177.22(10) no
N1 C8 C13 S1 . . . . -2.97(17) no
C11 C12 C13 C8 . . . . 0.2(2) no
C11 C12 C13 S1 . . . . -178.92(10) no
C19 C14 C15 C16 . . . . 1.6(2) no
S1 C14 C15 C16 . . . . -176.84(10) no
C14 C15 C16 C17 . . . . -4.2(2) no
C15 C16 C17 C18 . . . . 2.1(2) no
C16 C17 C18 C19 . . . . 2.5(2) no
C17 C18 C19 C14 . . . . -5.0(2) no
C17 C18 C19 N1 . . . . 175.60(12) no
C15 C14 C19 C18 . . . . 2.96(19) no
S1 C14 C19 C18 . . . . -178.56(10) no
C15 C14 C19 N1 . . . . -177.65(11) no
S1 C14 C19 N1 . . . . 0.83(16) no
C25 C20 C21 C22 . . . . -1.1(2) no
N3 C20 C21 C22 . . . . 179.69(13) no
C20 C21 C22 C23 . . . . -0.2(2) no
C21 C22 C23 C24 . . . . 1.3(2) no
C21 C22 C23 C26 . . . . -176.47(13) no
C22 C23 C24 C25 . . . . -1.1(2) no
C26 C23 C24 C25 . . . . 176.61(13) no
C23 C24 C25 C20 . . . . -0.2(2) no
C21 C20 C25 C24 . . . . 1.3(2) no
N3 C20 C25 C24 . . . . -179.52(12) no
C22 C23 C26 N4 . . . . 56.(7) no
C24 C23 C26 N4 . . . . -121.(7) no
C32 C27 C28 C29 . . . . 4.5(2) no
N3 C27 C28 C29 . . . . -176.36(13) no
C27 C28 C29 C30 . . . . -3.7(2) no
C28 C29 C30 C31 . . . . -0.7(2) no
C29 C30 C31 C32 . . . . 4.2(2) no
C28 C27 C32 C31 . . . . -1.0(2) no
N3 C27 C32 C31 . . . . 179.84(12) no
C28 C27 C32 S2 . . . . 179.17(11) no
N3 C27 C32 S2 . . . . 0.03(17) no
C30 C31 C32 C27 . . . . -3.3(2) no
C30 C31 C32 S2 . . . . 176.47(11) no
C38 C33 C34 C35 . . . . 0.9(2) no
S2 C33 C34 C35 . . . . -179.93(11) no
C33 C34 C35 C36 . . . . -1.6(2) no
C34 C35 C36 C37 . . . . 0.3(2) no
C35 C36 C37 C38 . . . . 1.7(2) no
C36 C37 C38 C33 . . . . -2.4(2) no
C36 C37 C38 N3 . . . . 178.10(13) no
C34 C33 C38 C37 . . . . 1.1(2) no
S2 C33 C38 C37 . . . . -178.08(11) no
C34 C33 C38 N3 . . . . -179.39(12) no
S2 C33 C38 N3 . . . . 1.43(17) no
C2 C1 N1 C19 . . . . -149.74(13) no
C6 C1 N1 C19 . . . . 31.39(19) no
C2 C1 N1 C8 . . . . 2.04(19) no
C6 C1 N1 C8 . . . . -176.84(12) no
C18 C19 N1 C1 . . . . -73.98(17) no
C14 C19 N1 C1 . . . . 106.63(15) no
C18 C19 N1 C8 . . . . 133.15(13) no
C14 C19 N1 C8 . . . . -46.24(16) no
C13 C8 N1 C1 . . . . -105.48(15) no
C9 C8 N1 C1 . . . . 74.33(17) no
C13 C8 N1 C19 . . . . 47.69(17) no
C9 C8 N1 C19 . . . . -132.51(13) no
C25 C20 N3 C38 . . . . -0.51(19) no
C21 C20 N3 C38 . . . . 178.68(12) no
C25 C20 N3 C27 . . . . 151.91(13) no
C21 C20 N3 C27 . . . . -28.90(19) no
C37 C38 N3 C20 . . . . -73.76(17) no
C33 C38 N3 C20 . . . . 106.73(14) no
C37 C38 N3 C27 . . . . 132.54(13) no
C33 C38 N3 C27 . . . . -46.96(17) no
C28 C27 N3 C20 . . . . 73.21(18) no
C32 C27 N3 C20 . . . . -107.66(14) no
C28 C27 N3 C38 . . . . -133.21(14) no
C32 C27 N3 C38 . . . . 45.93(17) no
C15 C14 S1 C13 . . . . -147.20(11) no
C19 C14 S1 C13 . . . . 34.31(11) no
C8 C13 S1 C14 . . . . -33.10(12) no
C12 C13 S1 C14 . . . . 146.05(11) no
C27 C32 S2 C33 . . . . -35.74(12) no
C31 C32 S2 C33 . . . . 144.44(11) no
C38 C33 S2 C32 . . . . 34.90(12) no
C34 C33 S2 C32 . . . . -144.28(11) no
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1555300'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2 O S'
_chemical_formula_weight         316.37

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   P2(1)/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                   12.3262(17)
_cell_length_b                   12.5229(18)
_cell_length_c                   9.8675(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.314(2)
_cell_angle_gamma                90.00
_cell_volume                     1454.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3850
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.53

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9558
_exptl_absorpt_correction_T_max  0.9775
_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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15081
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.50
_reflns_number_total             4411
_reflns_number_gt                3553
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0532P)²+0.2393P] 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         4411
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.27195(10) 0.77192(10) 0.40709(13) 0.0124(2) Uani 1 1 d . . .
C2 C 0.23934(10) 0.67420(10) 0.45268(14) 0.0151(2) Uani 1 1 d . . .
H2 H 0.1844 0.6731 0.5000 0.018 Uiso 1 1 calc R . .
C3 C 0.28784(11) 0.57977(11) 0.42799(14) 0.0158(3) Uani 1 1 d . . .
H3 H 0.2655 0.5157 0.4591 0.019 Uiso 1 1 calc R . .
C4 C 0.37032(11) 0.57956(11) 0.35656(14) 0.0162(3) Uani 1 1 d . . .
C5 C 0.40539(11) 0.67656(11) 0.31421(15) 0.0175(3) Uani 1 1 d . . .
H5 H 0.4614 0.6774 0.2685 0.021 Uiso 1 1 calc R . .
C6 C 0.35766(10) 0.77152(11) 0.33956(14) 0.0152(2) Uani 1 1 d . . .
H6 H 0.3824 0.8357 0.3117 0.018 Uiso 1 1 calc R . .
C7 C 0.41566(11) 0.47989(11) 0.32464(15) 0.0192(3) Uani 1 1 d . . .
C8 C 0.24556(10) 0.96504(10) 0.36732(14) 0.0134(2) Uani 1 1 d . . .
C9 C 0.34627(10) 1.01899(11) 0.43299(15) 0.0166(3) Uani 1 1 d . . .
H9 H 0.3978 0.9906 0.5139 0.020 Uiso 1 1 calc R . .
C10 C 0.36953(11) 1.11516(11) 0.37749(16) 0.0185(3) Uani 1 1 d . . .
H10 H 0.4371 1.1509 0.4209 0.022 Uiso 1 1 calc R . .
C11 C 0.29250(11) 1.15829(11) 0.25749(16) 0.0191(3) Uani 1 1 d . . .
H11 H 0.3094 1.2219 0.2194 0.023 Uiso 1 1 calc R . .
C12 C 0.19012(11) 1.10651(10) 0.19413(15) 0.0165(3) Uani 1 1 d . . .
H12 H 0.1376 1.1363 0.1151 0.020 Uiso 1 1 calc R . .
C13 C 0.16652(10) 1.00999(10) 0.24940(14) 0.0131(2) Uani 1 1 d . . .
C14 C 0.01477(10) 0.89655(10) 0.33436(14) 0.0130(2) Uani 1 1 d . . .
C15 C -0.09360(10) 0.89155(10) 0.35109(15) 0.0160(3) Uani 1 1 d . . .
H15 H -0.1565 0.9127 0.2774 0.019 Uiso 1 1 calc R . .
C16 C -0.10748(11) 0.85519(10) 0.47721(15) 0.0171(3) Uani 1 1 d . . .
H16 H -0.1801 0.8491 0.4867 0.021 Uiso 1 1 calc R . .
C17 C -0.01327(11) 0.82759(10) 0.58998(15) 0.0163(3) Uani 1 1 d . . .
H17 H -0.0227 0.8050 0.6756 0.020 Uiso 1 1 calc R . .
C18 C 0.09475(11) 0.83392(10) 0.57421(14) 0.0147(2) Uani 1 1 d . . .
H18 H 0.1580 0.8173 0.6502 0.018 Uiso 1 1 calc R . .
C19 C 0.10870(10) 0.86486(10) 0.44562(14) 0.0126(2) Uani 1 1 d . . .
N1 N 0.21892(9) 0.86740(8) 0.42524(12) 0.0140(2) Uani 1 1 d . . .
N2 N 0.44876(11) 0.39961(11) 0.29746(15) 0.0260(3) Uani 1 1 d . . .
S1 S 0.03458(3) 0.94596(3) 0.17587(3) 0.01540(9) 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 1.3995(16) . ?
C1 C2 1.4032(18) . ?
C1 C6 1.4069(18) . ?
C2 C3 1.3792(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3989(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3945(19) . ?
C4 C7 1.4403(19) . ?
C5 C6 1.3821(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.1464(19) . ?
C8 C9 1.3924(17) . ?
C8 C13 1.3947(17) . ?
C8 N1 1.4288(16) . ?
C9 C10 1.3878(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.3908(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.3919(18) . ?
C12 H12 0.9300 . ?
C13 S1 1.7640(13) . ?
C14 C19 1.3952(17) . ?
C14 C15 1.3952(17) . ?
C14 S1 1.7651(13) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3917(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.3881(18) . ?
C17 H17 0.9300 . ?
C18 C19 1.3855(18) . ?
C18 H18 0.9300 . ?
C19 N1 1.4317(15) . ?

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 C2 120.98(11) . . ?
N1 C1 C6 120.59(11) . . ?
C2 C1 C6 118.42(11) . . ?
C3 C2 C1 120.70(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.58(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.07(12) . . ?
C5 C4 C7 120.95(12) . . ?
C3 C4 C7 119.95(13) . . ?
C6 C5 C4 120.58(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.58(12) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N2 C7 C4 178.11(15) . . ?
C9 C8 C13 119.81(12) . . ?
C9 C8 N1 120.55(11) . . ?
C13 C8 N1 119.51(11) . . ?
C10 C9 C8 119.84(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.35(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.06(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.75(12) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.12(11) . . ?
C12 C13 S1 120.54(10) . . ?
C8 C13 S1 119.29(10) . . ?
C19 C14 C15 119.58(12) . . ?
C19 C14 S1 119.71(9) . . ?
C15 C14 S1 120.68(10) . . ?
C16 C15 C14 120.03(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.27(12) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.75(12) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.22(12) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.00(11) . . ?
C18 C19 N1 121.09(11) . . ?
C14 C19 N1 118.89(11) . . ?
C1 N1 C8 120.55(10) . . ?
C1 N1 C19 119.86(10) . . ?
C8 N1 C19 114.57(10) . . ?
C13 S1 C14 98.55(6) . . ?

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
N1 C1 C2 C3 176.66(12) . . . . ?
C6 C1 C2 C3 -1.91(18) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C2 C3 C4 C7 -176.58(12) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C7 C4 C5 C6 177.03(12) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
N1 C1 C6 C5 -176.20(11) . . . . ?
C2 C1 C6 C5 2.37(19) . . . . ?
C5 C4 C7 N2 -125(5) . . . . ?
C3 C4 C7 N2 53(5) . . . . ?
C13 C8 C9 C10 -2.5(2) . . . . ?
N1 C8 C9 C10 -178.33(12) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C11 C12 C13 S1 177.08(10) . . . . ?
C9 C8 C13 C12 2.49(19) . . . . ?
N1 C8 C13 C12 178.32(12) . . . . ?
C9 C8 C13 S1 -175.03(10) . . . . ?
N1 C8 C13 S1 0.81(17) . . . . ?
C19 C14 C15 C16 -0.12(19) . . . . ?
S1 C14 C15 C16 -178.36(10) . . . . ?
C14 C15 C16 C17 2.65(19) . . . . ?
C15 C16 C17 C18 -1.75(19) . . . . ?
C16 C17 C18 C19 -1.70(19) . . . . ?
C17 C18 C19 C14 4.22(19) . . . . ?
C17 C18 C19 N1 -177.24(11) . . . . ?
C15 C14 C19 C18 -3.31(18) . . . . ?
S1 C14 C19 C18 174.95(10) . . . . ?
C15 C14 C19 N1 178.12(11) . . . . ?
S1 C14 C19 N1 -3.62(16) . . . . ?
C2 C1 N1 C8 -174.40(11) . . . . ?
C6 C1 N1 C8 4.14(17) . . . . ?
C2 C1 N1 C19 -20.81(18) . . . . ?
C6 C1 N1 C19 157.72(12) . . . . ?
C9 C8 N1 C1 -76.75(16) . . . . ?
C13 C8 N1 C1 107.44(14) . . . . ?
C9 C8 N1 C19 128.35(13) . . . . ?
C13 C8 N1 C19 -47.46(16) . . . . ?
C18 C19 N1 C1 75.27(16) . . . . ?
C14 C19 N1 C1 -106.18(14) . . . . ?
C18 C19 N1 C8 -129.65(13) . . . . ?
C14 C19 N1 C8 48.91(16) . . . . ?
C12 C13 S1 C14 -142.56(11) . . . . ?
C8 C13 S1 C14 34.95(12) . . . . ?
C19 C14 S1 C13 -33.58(11) . . . . ?
C15 C14 S1 C13 144.66(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.074
