# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ab026
_database_code_depnum_ccdc_archive 'CCDC 1420524'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N3 S'
_chemical_formula_weight         305.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.3536(2)
_cell_length_b                   17.7010(4)
_cell_length_c                   9.8752(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.5047(12)
_cell_angle_gamma                90
_cell_volume                     1521.20(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.27

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13170
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3717
_reflns_number_gt                3076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.3131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3717
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78665(4) 0.02049(2) 0.90075(4) 0.04176(13) Uani 1 1 d . . . . .
N1 N 0.52911(14) 0.07488(8) 0.89807(14) 0.0419(3) Uani 1 1 d . . . . .
N2 N 0.49767(13) -0.01382(6) 0.71689(13) 0.0342(3) Uani 1 1 d . . . . .
N3 N 0.58717(12) -0.05935(6) 0.66608(12) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.7953(2) 0.08784(12) 1.0341(2) 0.0674(6) Uani 1 1 d D . . . .
C2 C 0.63935(19) 0.11653(9) 1.01560(18) 0.0485(4) Uani 1 1 d . . . . .
H2A H 0.6193 0.1091 1.1064 0.058 Uiso 1 1 calc R U . . .
H2B H 0.6318 0.1712 0.9925 0.058 Uiso 1 1 calc R U . . .
C3 C 0.58501(16) 0.02565(7) 0.82732(15) 0.0332(3) Uani 1 1 d . . . . .
C4 C 0.9330(5) 0.1240(2) 1.1100(5) 0.0672(12) Uani 0.55 1 d D . P A 1
H4A H 0.9328 0.1712 1.1556 0.081 Uiso 0.55 1 calc R U P A 1
H4B H 1.0275 0.1015 1.1163 0.081 Uiso 0.55 1 calc R U P A 1
C4' C 0.9083(6) 0.0900(3) 1.1696(6) 0.0644(13) Uani 0.45 1 d D . P A 2
H4C H 0.8867 0.1095 1.2497 0.077 Uiso 0.45 1 calc R U P A 2
H4D H 1.0084 0.0720 1.1836 0.077 Uiso 0.45 1 calc R U P A 2
C5 C 0.36671(17) 0.09173(10) 0.85260(18) 0.0452(4) Uani 1 1 d . . . . .
H5A H 0.3430 0.1368 0.7907 0.068 Uiso 1 1 calc R U . . .
H5B H 0.3404 0.1009 0.9386 0.068 Uiso 1 1 calc R U . . .
H5C H 0.3069 0.0489 0.7978 0.068 Uiso 1 1 calc R U . . .
C6 C 0.51232(14) -0.10148(7) 0.55602(14) 0.0300(3) Uani 1 1 d . . . . .
C7 C 0.59312(15) -0.15523(7) 0.49571(13) 0.0302(3) Uani 1 1 d . . . . .
C8 C 0.74855(16) -0.16852(8) 0.53353(15) 0.0357(3) Uani 1 1 d . . . . .
H8A H 0.8223 -0.1384 0.6052 0.043 Uiso 1 1 calc R U . . .
C9 C 0.79474(17) -0.22693(9) 0.46436(15) 0.0394(3) Uani 1 1 d . . . . .
H9A H 0.9011 -0.2372 0.4899 0.047 Uiso 1 1 calc R U . . .
C10 C 0.68693(18) -0.27040(8) 0.35835(16) 0.0395(3) Uani 1 1 d . . . . .
H10A H 0.7204 -0.3105 0.3133 0.047 Uiso 1 1 calc R U . . .
C11 C 0.53107(17) -0.25594(8) 0.31758(16) 0.0372(3) Uani 1 1 d . . . . .
H11A H 0.4578 -0.2850 0.2435 0.045 Uiso 1 1 calc R U . . .
C12 C 0.48385(15) -0.19822(7) 0.38689(14) 0.0315(3) Uani 1 1 d . . . . .
C13 C 0.33058(15) -0.17133(8) 0.37262(15) 0.0342(3) Uani 1 1 d . . . . .
C14 C 0.18635(17) -0.19447(9) 0.28005(18) 0.0462(4) Uani 1 1 d . . . . .
H14A H 0.1754 -0.2338 0.2114 0.055 Uiso 1 1 calc R U . . .
C15 C 0.05784(19) -0.15892(11) 0.2898(2) 0.0575(5) Uani 1 1 d . . . . .
H15A H -0.0419 -0.1742 0.2274 0.069 Uiso 1 1 calc R U . . .
C16 C 0.07355(18) -0.10160(11) 0.3891(2) 0.0561(4) Uani 1 1 d . . . . .
H16A H -0.0158 -0.0781 0.3939 0.067 Uiso 1 1 calc R U . . .
C17 C 0.21754(17) -0.07757(9) 0.48235(18) 0.0432(3) Uani 1 1 d . . . . .
H17A H 0.2274 -0.0380 0.5501 0.052 Uiso 1 1 calc R U . . .
C18 C 0.34672(15) -0.11287(8) 0.47399(15) 0.0337(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
S1 C1 1.7561(17) . ?
S1 C3 1.7575(14) . ?
N1 C3 1.3375(18) . ?
N1 C2 1.441(2) . ?
N1 C5 1.4485(19) . ?
N2 C3 1.3005(18) . ?
N2 N3 1.3821(15) . ?
N3 C6 1.2921(17) . ?
C1 C4' 1.369(5) . ?
C1 C4 1.386(4) . ?
C1 C2 1.491(2) . ?
C6 C7 1.4701(18) . ?
C6 C18 1.4752(18) . ?
C7 C8 1.3822(18) . ?
C7 C12 1.4047(18) . ?
C8 C9 1.3923(19) . ?
C9 C10 1.390(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.3889(19) . ?
C12 C13 1.4675(19) . ?
C13 C14 1.385(2) . ?
C13 C18 1.4090(19) . ?
C14 C15 1.391(2) . ?
C15 C16 1.381(3) . ?
C16 C17 1.390(2) . ?
C17 C18 1.389(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
C1 S1 C3 91.23(7) . . ?
C3 N1 C2 116.93(12) . . ?
C3 N1 C5 122.59(13) . . ?
C2 N1 C5 120.25(12) . . ?
C3 N2 N3 109.86(11) . . ?
C6 N3 N2 115.37(11) . . ?
C4' C1 C2 118.7(3) . . ?
C4 C1 C2 125.6(2) . . ?
C4' C1 S1 124.0(2) . . ?
C4 C1 S1 119.8(2) . . ?
C2 C1 S1 111.43(12) . . ?
N1 C2 C1 107.66(12) . . ?
N2 C3 N1 122.84(13) . . ?
N2 C3 S1 124.57(10) . . ?
N1 C3 S1 112.59(11) . . ?
N3 C6 C7 120.92(12) . . ?
N3 C6 C18 132.60(12) . . ?
C7 C6 C18 106.34(11) . . ?
C8 C7 C12 120.85(12) . . ?
C8 C7 C6 130.29(12) . . ?
C12 C7 C6 108.82(11) . . ?
C7 C8 C9 118.59(13) . . ?
C10 C9 C8 120.72(13) . . ?
C11 C10 C9 120.79(13) . . ?
C10 C11 C12 118.89(13) . . ?
C11 C12 C7 120.12(12) . . ?
C11 C12 C13 131.85(13) . . ?
C7 C12 C13 108.00(11) . . ?
C14 C13 C18 120.71(13) . . ?
C14 C13 C12 130.41(13) . . ?
C18 C13 C12 108.88(12) . . ?
C13 C14 C15 118.54(15) . . ?
C16 C15 C14 120.79(15) . . ?
C15 C16 C17 121.33(15) . . ?
C18 C17 C16 118.39(15) . . ?
C17 C18 C13 120.24(13) . . ?
C17 C18 C6 131.82(13) . . ?
C13 C18 C6 107.94(12) . . ?

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
C3 N2 N3 C6 179.87(11) . . . . ?
C3 S1 C1 C4' 150.0(4) . . . . ?
C3 S1 C1 C4 -163.5(3) . . . . ?
C3 S1 C1 C2 -2.59(17) . . . . ?
C3 N1 C2 C1 -4.0(2) . . . . ?
C5 N1 C2 C1 -178.62(16) . . . . ?
C4' C1 C2 N1 -150.1(3) . . . . ?
C4 C1 C2 N1 163.7(3) . . . . ?
S1 C1 C2 N1 4.1(2) . . . . ?
N3 N2 C3 N1 179.78(12) . . . . ?
N3 N2 C3 S1 -0.56(16) . . . . ?
C2 N1 C3 N2 -178.08(14) . . . . ?
C5 N1 C3 N2 -3.6(2) . . . . ?
C2 N1 C3 S1 2.22(18) . . . . ?
C5 N1 C3 S1 176.66(12) . . . . ?
C1 S1 C3 N2 -179.37(14) . . . . ?
C1 S1 C3 N1 0.32(14) . . . . ?
N2 N3 C6 C7 -177.04(11) . . . . ?
N2 N3 C6 C18 -2.1(2) . . . . ?
N3 C6 C7 C8 -3.3(2) . . . . ?
C18 C6 C7 C8 -179.46(13) . . . . ?
N3 C6 C7 C12 174.48(11) . . . . ?
C18 C6 C7 C12 -1.64(14) . . . . ?
C12 C7 C8 C9 -1.8(2) . . . . ?
C6 C7 C8 C9 175.79(13) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C10 C11 C12 C7 0.38(19) . . . . ?
C10 C11 C12 C13 -177.47(14) . . . . ?
C8 C7 C12 C11 1.27(19) . . . . ?
C6 C7 C12 C11 -176.80(11) . . . . ?
C8 C7 C12 C13 179.59(12) . . . . ?
C6 C7 C12 C13 1.52(14) . . . . ?
C11 C12 C13 C14 -2.9(3) . . . . ?
C7 C12 C13 C14 179.09(15) . . . . ?
C11 C12 C13 C18 177.23(14) . . . . ?
C7 C12 C13 C18 -0.82(15) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
C12 C13 C14 C15 179.84(16) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?
C16 C17 C18 C6 -179.58(15) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C12 C13 C18 C17 179.93(13) . . . . ?
C14 C13 C18 C6 179.87(13) . . . . ?
C12 C13 C18 C6 -0.22(15) . . . . ?
N3 C6 C18 C17 5.5(3) . . . . ?
C7 C6 C18 C17 -179.05(15) . . . . ?
N3 C6 C18 C13 -174.36(14) . . . . ?
C7 C6 C18 C13 1.12(14) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.048



