# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_sa3433b
_database_code_depnum_ccdc_archive 'CCDC 1030356'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_audit_creation_date             2014-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H13 N S'
_chemical_formula_sum            'C16 H13 N S'
_chemical_formula_weight         251.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.7076(11)
_cell_length_b                   20.718(4)
_cell_length_c                   21.125(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2498.0(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7368
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4845
_cell_measurement_theta_min      2.1897
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15510
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         3.498
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3331
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0931
_diffrn_orient_matrix_UB_12      -0.0980
_diffrn_orient_matrix_UB_13      0.1115
_diffrn_orient_matrix_UB_21      0.0387
_diffrn_orient_matrix_UB_22      -0.0044
_diffrn_orient_matrix_UB_23      0.0285
_diffrn_orient_matrix_UB_31      -0.0128
_diffrn_orient_matrix_UB_32      0.0390
_diffrn_orient_matrix_UB_33      0.0236
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2624
_reflns_number_total             2862
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.304
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+2.4999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1774
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.79190(14) 0.04508(4) 0.45504(4) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.5090(4) 0.15758(12) 0.45721(12) 0.0320(6) Uani 1 1 d . . . . .
C1 C 0.5094(5) 0.21412(14) 0.42181(15) 0.0328(7) Uani 1 1 d . . . . .
C2 C 0.3464(6) 0.26405(16) 0.42286(19) 0.0437(8) Uani 1 1 d . . . . .
H2 H 0.2212 0.2639 0.4510 0.052 Uiso 1 1 calc R . . . .
C3 C 0.3787(7) 0.31374(18) 0.3803(2) 0.0546(11) Uani 1 1 d . . . . .
H3 H 0.2727 0.3478 0.3797 0.066 Uiso 1 1 calc R . . . .
C4 C 0.5666(7) 0.31413(17) 0.3380(2) 0.0513(10) Uani 1 1 d . . . . .
H4 H 0.5826 0.3483 0.3098 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7290(7) 0.26472(16) 0.33721(17) 0.0422(8) Uani 1 1 d . . . . .
H5 H 0.8540 0.2656 0.3090 0.051 Uiso 1 1 calc R . . . .
C6 C 0.7026(5) 0.21342(14) 0.37951(15) 0.0332(7) Uani 1 1 d . . . . .
C7 C 0.8229(5) 0.15348(14) 0.39073(14) 0.0300(6) Uani 1 1 d . . . . .
C8 C 0.6977(5) 0.12216(14) 0.43742(14) 0.0295(6) Uani 1 1 d . . . . .
C9 C 0.3433(6) 0.14031(16) 0.50636(16) 0.0389(8) Uani 1 1 d . . . . .
H9A H 0.3651 0.1681 0.5423 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.3684 0.0963 0.5188 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.1866 0.1451 0.4905 0.058 Uiso 1 1 calc GR . . . .
C10 C 1.0122(5) 0.11445(15) 0.36772(14) 0.0294(6) Uani 1 1 d . . . . .
C11 C 1.0130(5) 0.05300(14) 0.39717(14) 0.0301(6) Uani 1 1 d . . . . .
C12 C 1.1747(5) 0.00552(16) 0.38143(15) 0.0347(7) Uani 1 1 d . . . . .
H12 H 1.1692 -0.0346 0.4011 0.042 Uiso 1 1 calc R . . . .
C13 C 1.3441(6) 0.01845(17) 0.33623(15) 0.0364(7) Uani 1 1 d . . . . .
C14 C 1.3498(6) 0.07984(17) 0.30901(15) 0.0374(8) Uani 1 1 d . . . . .
H14 H 1.4671 0.0892 0.2799 0.045 Uiso 1 1 calc R . . . .
C15 C 1.1888(6) 0.12696(16) 0.32357(14) 0.0345(7) Uani 1 1 d . . . . .
H15 H 1.1975 0.1671 0.3040 0.041 Uiso 1 1 calc R . . . .
C16 C 1.5175(7) -0.03261(18) 0.31653(18) 0.0482(9) Uani 1 1 d . . . . .
H16A H 1.5339 -0.0638 0.3499 0.072 Uiso 1 1 calc GR . . . .
H16B H 1.6665 -0.0129 0.3082 0.072 Uiso 1 1 calc GR . . . .
H16C H 1.4623 -0.0537 0.2789 0.072 Uiso 1 1 calc GR . . . .


_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 C8 1.725(3) . ?
S1 C11 1.764(3) . ?
N1 C1 1.390(4) . ?
N1 C8 1.369(4) . ?
N1 C9 1.449(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.419(5) . ?
C2 C3 1.379(6) . ?
C3 C4 1.396(6) . ?
C4 C5 1.381(5) . ?
C5 C6 1.397(5) . ?
C6 C7 1.439(4) . ?
C7 C8 1.380(4) . ?
C7 C10 1.435(4) . ?
C10 C11 1.417(4) . ?
C10 C15 1.398(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.385(4) . ?
C13 C14 1.396(5) . ?
C13 C16 1.507(5) . ?
C14 C15 1.375(5) . ?

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
C8 S1 C11 89.27(14) . . ?
C1 N1 C9 126.5(3) . . ?
C8 N1 C1 106.6(3) . . ?
C8 N1 C9 126.9(3) . . ?
N1 C1 C2 128.1(3) . . ?
N1 C1 C6 109.3(3) . . ?
C2 C1 C6 122.5(3) . . ?
C3 C2 C1 117.1(4) . . ?
C2 C3 C4 121.6(3) . . ?
C5 C4 C3 121.3(4) . . ?
C4 C5 C6 118.9(4) . . ?
C1 C6 C7 106.0(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 135.3(3) . . ?
C8 C7 C6 106.1(3) . . ?
C8 C7 C10 111.5(3) . . ?
C10 C7 C6 142.2(3) . . ?
N1 C8 S1 132.5(2) . . ?
N1 C8 C7 111.9(3) . . ?
C7 C8 S1 115.4(2) . . ?
C11 C10 C7 111.1(3) . . ?
C15 C10 C7 131.7(3) . . ?
C15 C10 C11 117.2(3) . . ?
C10 C11 S1 112.7(2) . . ?
C12 C11 S1 125.1(2) . . ?
C12 C11 C10 122.2(3) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 C16 120.9(3) . . ?
C14 C13 C16 120.7(3) . . ?
C15 C14 C13 122.6(3) . . ?
C14 C15 C10 120.0(3) . . ?

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
S1 C11 C12 C13 -178.2(2) . . . . ?
N1 C1 C2 C3 -176.4(3) . . . . ?
N1 C1 C6 C5 177.0(3) . . . . ?
N1 C1 C6 C7 -0.2(3) . . . . ?
C1 N1 C8 S1 -173.6(3) . . . . ?
C1 N1 C8 C7 0.4(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C6 C7 C8 0.5(3) . . . . ?
C1 C6 C7 C10 174.5(4) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 C7 176.1(3) . . . . ?
C5 C6 C7 C8 -176.0(4) . . . . ?
C5 C6 C7 C10 -2.0(7) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C7 C8 S1 174.6(2) . . . . ?
C6 C7 C8 N1 -0.6(3) . . . . ?
C6 C7 C10 C11 -171.1(4) . . . . ?
C6 C7 C10 C15 9.6(7) . . . . ?
C7 C10 C11 S1 -2.8(3) . . . . ?
C7 C10 C11 C12 177.8(3) . . . . ?
C7 C10 C15 C14 -178.9(3) . . . . ?
C8 S1 C11 C10 1.7(2) . . . . ?
C8 S1 C11 C12 -179.0(3) . . . . ?
C8 N1 C1 C2 177.0(3) . . . . ?
C8 N1 C1 C6 -0.1(3) . . . . ?
C8 C7 C10 C11 2.7(4) . . . . ?
C8 C7 C10 C15 -176.6(3) . . . . ?
C9 N1 C1 C2 -4.1(5) . . . . ?
C9 N1 C1 C6 178.8(3) . . . . ?
C9 N1 C8 S1 7.5(5) . . . . ?
C9 N1 C8 C7 -178.4(3) . . . . ?
C10 C7 C8 S1 -1.5(3) . . . . ?
C10 C7 C8 N1 -176.7(2) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C11 S1 C8 N1 173.8(3) . . . . ?
C11 S1 C8 C7 -0.1(2) . . . . ?
C11 C10 C15 C14 1.9(4) . . . . ?
C11 C12 C13 C14 1.6(5) . . . . ?
C11 C12 C13 C16 -178.1(3) . . . . ?
C12 C13 C14 C15 -2.5(5) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C15 C10 C11 S1 176.6(2) . . . . ?
C15 C10 C11 C12 -2.8(4) . . . . ?
C16 C13 C14 C15 177.1(3) . . . . ?

