# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1039019'
_audit_update_record             
;
2014-12-12 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_date             2014-11-05T15:56:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C21 H15 N3 S1'
_chemical_formula_sum            'C21 H15 N3 S'
_chemical_formula_weight         341.42

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7003(4)
_cell_length_b                   8.7382(5)
_cell_length_c                   17.506(1)
_cell_angle_alpha                82.547(6)
_cell_angle_beta                 84.108(6)
_cell_angle_gamma                87.123(5)
_cell_volume                     859.44(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7815
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      27.49

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            30819
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             3941
_reflns_number_gt                2704
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0381P)²+0.2550P] 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_number_reflns         3941
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0996
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.213

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C -0.1038(4) 0.6939(3) 0.03822(13) 0.0700(6) Uani 1 d . . .
H1 H -0.2353 0.64 0.0607 0.084 Uiso 1 calc R . .
C2 C -0.0685(5) 0.7298(3) -0.04204(14) 0.0834(8) Uani 1 d . . .
H2 H -0.1786 0.7012 -0.0728 0.1 Uiso 1 calc R . .
C3 C 0.1243(5) 0.8058(3) -0.07565(12) 0.0649(6) Uani 1 d . . .
H3 H 0.1478 0.8284 -0.1292 0.078 Uiso 1 calc R . .
C4 C 0.2828(4) 0.8488(3) -0.03044(13) 0.0731(7) Uani 1 d . . .
H4 H 0.4163 0.9002 -0.0532 0.088 Uiso 1 calc R . .
C5 C 0.2469(4) 0.8165(3) 0.04932(11) 0.0614(6) Uani 1 d . . .
H5 H 0.3548 0.8487 0.0798 0.074 Uiso 1 calc R . .
C6 C 0.0551(3) 0.73808(19) 0.08381(9) 0.0395(4) Uani 1 d . . .
C7 C -0.1772(3) 0.8015(2) 0.20308(11) 0.0493(5) Uani 1 d . . .
H7A H -0.2643 0.7371 0.2438 0.074 Uiso 1 calc R . .
H7B H -0.2808 0.8438 0.1651 0.074 Uiso 1 calc R . .
H7C H -0.1116 0.884 0.2243 0.074 Uiso 1 calc R . .
C8 C 0.1747(3) 0.62660(19) 0.21046(9) 0.0378(4) Uani 1 d . . .
C9 C 0.1664(3) 0.6300(2) 0.29112(10) 0.0421(4) Uani 1 d . . .
H9 H 0.05 0.6903 0.3155 0.05 Uiso 1 calc R . .
C10 C 0.3279(3) 0.5454(2) 0.33401(10) 0.0421(4) Uani 1 d . . .
H10 H 0.3185 0.5505 0.387 0.051 Uiso 1 calc R . .
C11 C 0.5066(3) 0.45163(19) 0.30069(9) 0.0378(4) Uani 1 d . . .
C12 C 0.5109(3) 0.44627(19) 0.22085(9) 0.0406(4) Uani 1 d . . .
H12 H 0.6255 0.3842 0.1968 0.049 Uiso 1 calc R . .
C13 C 0.3511(3) 0.53002(19) 0.17724(9) 0.0402(4) Uani 1 d . . .
H13 H 0.3593 0.5229 0.1245 0.048 Uiso 1 calc R . .
C14 C 0.6799(3) 0.36675(19) 0.34695(9) 0.0410(4) Uani 1 d . . .
C15 C 0.7009(4) 0.3628(3) 0.42511(11) 0.0634(6) Uani 1 d . . .
H15 H 0.5988 0.4179 0.4574 0.076 Uiso 1 calc R . .
C16 C 0.8879(4) 0.2694(3) 0.45109(11) 0.0621(6) Uani 1 d . . .
H16 H 0.923 0.2568 0.5023 0.074 Uiso 1 calc R . .
C17 C 1.0171(3) 0.1969(2) 0.39410(9) 0.0426(4) Uani 1 d . . .
C18 C 1.2109(3) 0.0938(2) 0.40685(10) 0.0433(4) Uani 1 d . . .
H18 H 1.2455 0.0754 0.4581 0.052 Uiso 1 calc R . .
C19 C 1.3566(3) 0.0164(2) 0.35709(9) 0.0403(4) Uani 1 d . . .
C20 C 1.5424(3) -0.0852(2) 0.38535(10) 0.0476(5) Uani 1 d . . .
C21 C 1.3407(3) 0.0325(2) 0.27526(10) 0.0423(4) Uani 1 d . . .
N1 N 0.0133(3) 0.70946(18) 0.16666(8) 0.0459(4) Uani 1 d . . .
N2 N 1.3313(3) 0.0452(2) 0.20983(9) 0.0634(5) Uani 1 d . . .
N3 N 1.6896(3) -0.1659(2) 0.40879(10) 0.0685(5) Uani 1 d . . .
S1 S 0.89872(8) 0.25004(5) 0.30623(2) 0.03936(14) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 1.367(3) . ?
C1 C2 1.395(3) . ?
C1 H1 0.93 . ?
C2 C3 1.354(3) . ?
C2 H2 0.93 . ?
C3 C4 1.357(3) . ?
C3 H3 0.93 . ?
C4 C5 1.384(3) . ?
C4 H4 0.93 . ?
C5 C6 1.365(3) . ?
C5 H5 0.93 . ?
C6 N1 1.436(2) . ?
C7 N1 1.461(2) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 N1 1.375(2) . ?
C8 C13 1.408(2) . ?
C8 C9 1.412(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.93 . ?
C10 C11 1.403(2) . ?
C10 H10 0.93 . ?
C11 C12 1.402(2) . ?
C11 C14 1.455(2) . ?
C12 C13 1.371(2) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 C15 1.382(2) . ?
C14 S1 1.7269(17) . ?
C15 C16 1.387(3) . ?
C15 H15 0.93 . ?
C16 C17 1.380(3) . ?
C16 H16 0.93 . ?
C17 C18 1.407(2) . ?
C17 S1 1.7416(16) . ?
C18 C19 1.362(2) . ?
C18 H18 0.93 . ?
C19 C21 1.433(2) . ?
C19 C20 1.433(3) . ?
C20 N3 1.143(2) . ?
C21 N2 1.143(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
C6 C1 C2 119.9(2) . . ?
C6 C1 H1 120 . . ?
C2 C1 H1 120 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.80(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.82(18) . . ?
C5 C6 N1 120.78(16) . . ?
C1 C6 N1 120.32(17) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C13 121.40(15) . . ?
N1 C8 C9 121.71(15) . . ?
C13 C8 C9 116.86(15) . . ?
C10 C9 C8 120.86(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 122.29(16) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 116.58(15) . . ?
C12 C11 C14 122.16(15) . . ?
C10 C11 C14 121.25(15) . . ?
C13 C12 C11 121.83(16) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C8 121.55(15) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C15 C14 C11 128.78(16) . . ?
C15 C14 S1 109.86(13) . . ?
C11 C14 S1 121.36(12) . . ?
C14 C15 C16 114.00(17) . . ?
C14 C15 H15 123 . . ?
C16 C15 H15 123 . . ?
C17 C16 C15 113.96(16) . . ?
C17 C16 H16 123 . . ?
C15 C16 H16 123 . . ?
C16 C17 C18 124.32(16) . . ?
C16 C17 S1 109.46(13) . . ?
C18 C17 S1 126.21(13) . . ?
C19 C18 C17 131.10(16) . . ?
C19 C18 H18 114.5 . . ?
C17 C18 H18 114.5 . . ?
C18 C19 C21 123.69(15) . . ?
C18 C19 C20 120.15(15) . . ?
C21 C19 C20 116.14(15) . . ?
N3 C20 C19 179.18(19) . . ?
N2 C21 C19 179.1(2) . . ?
C8 N1 C6 121.37(14) . . ?
C8 N1 C7 120.51(14) . . ?
C6 N1 C7 116.58(14) . . ?
C14 S1 C17 92.71(8) . . ?

