# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1828815'
_audit_update_record             
;
2018-03-11 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TPA-BT-CN
_chemical_name_common            TPA-BT-CN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N4 S'
_chemical_formula_weight         404.48

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                   15.987(3)
_cell_length_b                   11.2031(19)
_cell_length_c                   11.3627(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.358(5)
_cell_angle_gamma                90.00
_cell_volume                     2001.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7103
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.06

_exptl_crystal_description       niddle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19757
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.85
_reflns_number_total             3531
_reflns_number_gt                2560
_reflns_threshold_expression     >2σ(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-2014 (Sheldrick 2014)'
_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 > 2σ(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)+(0.0851P)²+0.4848P] 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         3531
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.94923(14) 0.71815(19) 0.38795(18) 0.0329(5) Uani 1 1 d . . .
C2 C 0.98309(14) 0.6293(2) 0.32051(18) 0.0332(5) Uani 1 1 d . . .
C3 C 0.95674(13) 0.5141(2) 0.32962(18) 0.0358(5) Uani 1 1 d . . .
H3 H 0.9779 0.4548 0.2857 0.043 Uiso 1 1 calc R . .
C4 C 0.89830(14) 0.48261(19) 0.40388(18) 0.0344(5) Uani 1 1 d . . .
H4 H 0.8831 0.4027 0.4074 0.041 Uiso 1 1 calc R . .
C5 C 0.86245(13) 0.56393(19) 0.47170(18) 0.0311(5) Uani 1 1 d . . .
C6 C 0.88899(13) 0.68592(18) 0.46174(18) 0.0308(5) Uani 1 1 d . . .
C7 C 0.80337(13) 0.52604(18) 0.54999(18) 0.0315(5) Uani 1 1 d . . .
C8 C 0.75362(15) 0.4223(2) 0.5255(2) 0.0373(5) Uani 1 1 d . . .
H8 H 0.7564 0.3793 0.4563 0.045 Uiso 1 1 calc R . .
C9 C 0.70104(14) 0.3824(2) 0.6004(2) 0.0373(5) Uani 1 1 d . . .
H9 H 0.6691 0.3134 0.5812 0.045 Uiso 1 1 calc R . .
C10 C 0.69506(13) 0.4442(2) 0.70497(19) 0.0332(5) Uani 1 1 d . . .
C11 C 0.74338(14) 0.5479(2) 0.72953(19) 0.0353(5) Uani 1 1 d . . .
H11 H 0.7402 0.5908 0.7986 0.042 Uiso 1 1 calc R . .
C12 C 0.79555(14) 0.58821(19) 0.65417(19) 0.0356(5) Uani 1 1 d . . .
H12 H 0.8263 0.6583 0.6729 0.043 Uiso 1 1 calc R . .
C13 C 0.50945(16) 0.4091(2) 0.6375(2) 0.0460(6) Uani 1 1 d . . .
H13 H 0.5306 0.4734 0.6001 0.055 Uiso 1 1 calc R . .
C14 C 0.42876(16) 0.3666(2) 0.5926(2) 0.0534(7) Uani 1 1 d . . .
H14 H 0.3969 0.4013 0.5247 0.064 Uiso 1 1 calc R . .
C15 C 0.39592(19) 0.2744(3) 0.6473(3) 0.0732(10) Uani 1 1 d . . .
H15 H 0.3417 0.2456 0.6173 0.088 Uiso 1 1 calc R . .
C16 C 0.4440(2) 0.2241(3) 0.7477(3) 0.0965(14) Uani 1 1 d . . .
H16 H 0.4213 0.1626 0.7871 0.116 Uiso 1 1 calc R . .
C17 C 0.52582(19) 0.2641(3) 0.7910(3) 0.0724(10) Uani 1 1 d . . .
H17 H 0.5584 0.2272 0.8571 0.087 Uiso 1 1 calc R . .
C18 C 0.55914(14) 0.3582(2) 0.7363(2) 0.0377(5) Uani 1 1 d . . .
C19 C 0.66692(14) 0.4213(2) 0.90843(19) 0.0384(6) Uani 1 1 d . . .
C20 C 0.61051(18) 0.4688(3) 0.9753(2) 0.0701(9) Uani 1 1 d . . .
H20 H 0.5554 0.4886 0.9388 0.084 Uiso 1 1 calc R . .
C21 C 0.6369(2) 0.4864(4) 1.0972(3) 0.0912(13) Uani 1 1 d . . .
H21 H 0.5988 0.5170 1.1425 0.109 Uiso 1 1 calc R . .
C22 C 0.7181(2) 0.4595(3) 1.1517(2) 0.0707(9) Uani 1 1 d . . .
H22 H 0.7354 0.4729 1.2333 0.085 Uiso 1 1 calc R . .
C23 C 0.77320(17) 0.4133(2) 1.0863(2) 0.0533(7) Uani 1 1 d . . .
H23 H 0.8284 0.3947 1.1233 0.064 Uiso 1 1 calc R . .
C24 C 0.74816(15) 0.3934(2) 0.9648(2) 0.0411(6) Uani 1 1 d . . .
H24 H 0.7865 0.3610 0.9209 0.049 Uiso 1 1 calc R . .
C25 C 1.04229(15) 0.6634(2) 0.2448(2) 0.0405(6) Uani 1 1 d . . .
N1 N 0.96713(12) 0.83599(16) 0.38857(16) 0.0379(5) Uani 1 1 d . . .
N2 N 0.86130(12) 0.78243(16) 0.51580(17) 0.0386(5) Uani 1 1 d . . .
N3 N 0.64160(12) 0.40346(17) 0.78298(16) 0.0399(5) Uani 1 1 d . . .
N4 N 1.08750(15) 0.6934(2) 0.1832(2) 0.0551(6) Uani 1 1 d . . .
S1 S 0.90993(4) 0.89687(5) 0.47467(5) 0.0426(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.351(3) . ?
C1 C2 1.422(3) . ?
C1 C6 1.432(3) . ?
C2 C3 1.367(3) . ?
C2 C25 1.440(3) . ?
C3 C4 1.412(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.442(3) . ?
C5 C7 1.472(3) . ?
C6 N2 1.356(3) . ?
C7 C12 1.398(3) . ?
C7 C8 1.408(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(3) . ?
C10 N3 1.413(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.377(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 N3 1.423(3) . ?
C19 C24 1.377(3) . ?
C19 C20 1.385(3) . ?
C19 N3 1.424(3) . ?
C20 C21 1.388(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.354(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N4 1.143(3) . ?
N1 S1 1.6063(19) . ?
N2 S1 1.6116(19) . ?

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 125.9(2) . . ?
N1 C1 C6 114.05(19) . . ?
C2 C1 C6 120.02(19) . . ?
C3 C2 C1 117.90(19) . . ?
C3 C2 C25 122.7(2) . . ?
C1 C2 C25 119.4(2) . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 123.6(2) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C6 115.06(19) . . ?
C4 C5 C7 121.49(19) . . ?
C6 C5 C7 123.43(19) . . ?
N2 C6 C1 111.89(18) . . ?
N2 C6 C5 126.55(19) . . ?
C1 C6 C5 121.56(19) . . ?
C12 C7 C8 116.46(19) . . ?
C12 C7 C5 122.20(19) . . ?
C8 C7 C5 121.32(19) . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 117.7(2) . . ?
C9 C10 N3 121.1(2) . . ?
C11 C10 N3 121.27(19) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C18 C13 C14 121.4(2) . . ?
C18 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 118.1(2) . . ?
C17 C18 N3 120.8(2) . . ?
C13 C18 N3 121.1(2) . . ?
C24 C19 C20 119.0(2) . . ?
C24 C19 N3 120.5(2) . . ?
C20 C19 N3 120.5(2) . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.4(2) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
N4 C25 C2 177.7(3) . . ?
C1 N1 S1 105.96(15) . . ?
C6 N2 S1 106.80(15) . . ?
C10 N3 C18 120.36(18) . . ?
C10 N3 C19 119.17(18) . . ?
C18 N3 C19 120.06(18) . . ?
N1 S1 N2 101.30(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
N1 C1 C2 C3 -179.1(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
N1 C1 C2 C25 0.2(3) . . . . ?
C6 C1 C2 C25 178.74(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C25 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C7 -178.49(19) . . . . ?
N1 C1 C6 N2 1.0(3) . . . . ?
C2 C1 C6 N2 -177.71(18) . . . . ?
N1 C1 C6 C5 179.97(19) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C4 C5 C6 N2 177.8(2) . . . . ?
C7 C5 C6 N2 -3.7(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C7 C5 C6 C1 177.51(19) . . . . ?
C4 C5 C7 C12 151.0(2) . . . . ?
C6 C5 C7 C12 -27.4(3) . . . . ?
C4 C5 C7 C8 -26.9(3) . . . . ?
C6 C5 C7 C8 154.7(2) . . . . ?
C12 C7 C8 C9 -1.0(3) . . . . ?
C5 C7 C8 C9 176.9(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 N3 -179.6(2) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
N3 C10 C11 C12 180.0(2) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C8 C7 C12 C11 1.5(3) . . . . ?
C5 C7 C12 C11 -176.47(19) . . . . ?
C18 C13 C14 C15 1.5(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 -2.0(6) . . . . ?
C15 C16 C17 C18 2.5(6) . . . . ?
C16 C17 C18 C13 -1.0(5) . . . . ?
C16 C17 C18 N3 177.1(3) . . . . ?
C14 C13 C18 C17 -0.9(4) . . . . ?
C14 C13 C18 N3 -179.1(2) . . . . ?
C24 C19 C20 C21 -0.4(5) . . . . ?
N3 C19 C20 C21 -179.4(3) . . . . ?
C19 C20 C21 C22 1.1(6) . . . . ?
C20 C21 C22 C23 -1.0(6) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C20 C19 C24 C23 -0.4(4) . . . . ?
N3 C19 C24 C23 178.6(2) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C3 C2 C25 N4 131(7) . . . . ?
C1 C2 C25 N4 -48(7) . . . . ?
C2 C1 N1 S1 177.82(18) . . . . ?
C6 C1 N1 S1 -0.8(2) . . . . ?
C1 C6 N2 S1 -0.7(2) . . . . ?
C5 C6 N2 S1 -179.55(17) . . . . ?
C9 C10 N3 C18 -41.3(3) . . . . ?
C11 C10 N3 C18 138.4(2) . . . . ?
C9 C10 N3 C19 146.1(2) . . . . ?
C11 C10 N3 C19 -34.1(3) . . . . ?
C17 C18 N3 C10 143.7(3) . . . . ?
C13 C18 N3 C10 -38.2(3) . . . . ?
C17 C18 N3 C19 -43.8(4) . . . . ?
C13 C18 N3 C19 134.3(2) . . . . ?
C24 C19 N3 C10 -47.4(3) . . . . ?
C20 C19 N3 C10 131.6(3) . . . . ?
C24 C19 N3 C18 140.0(2) . . . . ?
C20 C19 N3 C18 -41.0(3) . . . . ?
C1 N1 S1 N2 0.39(16) . . . . ?
C6 N2 S1 N1 0.18(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.819
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_a_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1828816'
_audit_update_record             
;
2018-03-11 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ACR-BT-CN
_chemical_name_common            ACR-BT-CN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N4 S'
_chemical_formula_weight         444.54

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   C2/c

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

_cell_length_a                   36.066(11)
_cell_length_b                   7.737(2)
_cell_length_c                   16.095(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.584(9)
_cell_angle_gamma                90.00
_cell_volume                     4489(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4526
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      24.11

_exptl_crystal_description       niddle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.970
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22693
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3961
_reflns_number_gt                2394
_reflns_threshold_expression     >2σ(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-2014 (Sheldrick 2014)'
_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 > 2σ(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)+(0.0639P)²+5.6710P] 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         3961
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.49301(9) 0.7565(5) 0.4987(2) 0.0466(9) Uani 1 1 d . . .
C2 C 0.50308(10) 0.6993(5) 0.4192(2) 0.0495(9) Uani 1 1 d . . .
C3 C 0.53869(10) 0.6438(5) 0.4086(2) 0.0487(9) Uani 1 1 d . . .
H3 H 0.5456 0.6041 0.3567 0.058 Uiso 1 1 calc R . .
C4 C 0.56542(9) 0.6460(4) 0.47578(18) 0.0406(8) Uani 1 1 d . . .
H4 H 0.5894 0.6080 0.4659 0.049 Uiso 1 1 calc R . .
C5 C 0.55743(9) 0.7016(4) 0.55426(18) 0.0360(8) Uani 1 1 d . . .
C6 C 0.52012(9) 0.7579(4) 0.56609(18) 0.0401(8) Uani 1 1 d . . .
C7 C 0.58579(9) 0.7063(4) 0.62268(17) 0.0329(7) Uani 1 1 d . . .
C8 C 0.61350(8) 0.5812(4) 0.63013(16) 0.0308(7) Uani 1 1 d . . .
H8 H 0.6134 0.4918 0.5915 0.037 Uiso 1 1 calc R . .
C9 C 0.64130(8) 0.5817(4) 0.69160(16) 0.0284(7) Uani 1 1 d . . .
C10 C 0.64069(8) 0.7149(4) 0.75111(16) 0.0279(7) Uani 1 1 d . . .
C11 C 0.61384(8) 0.8457(4) 0.74295(17) 0.0322(7) Uani 1 1 d . . .
H11 H 0.6142 0.9372 0.7804 0.039 Uiso 1 1 calc R . .
C12 C 0.58696(9) 0.8409(4) 0.68040(17) 0.0354(8) Uani 1 1 d . . .
H12 H 0.5694 0.9286 0.6766 0.043 Uiso 1 1 calc R . .
C13 C 0.67077(8) 0.4406(4) 0.69379(17) 0.0304(7) Uani 1 1 d . . .
C14 C 0.65178(10) 0.2663(4) 0.7094(2) 0.0461(9) Uani 1 1 d . . .
H14A H 0.6701 0.1762 0.7112 0.069 Uiso 1 1 calc R . .
H14B H 0.6340 0.2434 0.6654 0.069 Uiso 1 1 calc R . .
H14C H 0.6394 0.2705 0.7615 0.069 Uiso 1 1 calc R . .
C15 C 0.68982(10) 0.4333(4) 0.60876(17) 0.0429(9) Uani 1 1 d . . .
H15A H 0.7085 0.3449 0.6101 0.064 Uiso 1 1 calc R . .
H15B H 0.7011 0.5430 0.5977 0.064 Uiso 1 1 calc R . .
H15C H 0.6717 0.4076 0.5658 0.064 Uiso 1 1 calc R . .
C16 C 0.69995(8) 0.4719(4) 0.76288(16) 0.0286(7) Uani 1 1 d . . .
C17 C 0.73134(9) 0.3653(4) 0.77011(18) 0.0352(8) Uani 1 1 d . . .
H17 H 0.7347 0.2802 0.7302 0.042 Uiso 1 1 calc R . .
C18 C 0.75744(9) 0.3815(4) 0.83377(19) 0.0403(8) Uani 1 1 d . . .
H18 H 0.7784 0.3112 0.8354 0.048 Uiso 1 1 calc R . .
C19 C 0.75223(9) 0.5025(4) 0.89491(18) 0.0379(8) Uani 1 1 d . . .
H19 H 0.7693 0.5122 0.9391 0.045 Uiso 1 1 calc R . .
C20 C 0.72159(9) 0.6098(4) 0.89052(17) 0.0325(7) Uani 1 1 d . . .
H20 H 0.7179 0.6901 0.9325 0.039 Uiso 1 1 calc R . .
C21 C 0.69599(8) 0.5993(4) 0.82379(16) 0.0270(7) Uani 1 1 d . . .
C22 C 0.66352(8) 0.8518(4) 0.87939(16) 0.0297(7) Uani 1 1 d . . .
C23 C 0.68591(9) 0.9959(4) 0.87701(18) 0.0352(8) Uani 1 1 d . . .
H23 H 0.7035 1.0064 0.8360 0.042 Uiso 1 1 calc R . .
C24 C 0.68223(10) 1.1248(4) 0.93575(19) 0.0421(8) Uani 1 1 d . . .
H24 H 0.6974 1.2219 0.9343 0.050 Uiso 1 1 calc R . .
C25 C 0.65625(10) 1.1099(5) 0.9961(2) 0.0463(9) Uani 1 1 d . . .
H25 H 0.6540 1.1965 1.0357 0.056 Uiso 1 1 calc R . .
C26 C 0.63330(10) 0.9662(5) 0.99825(18) 0.0441(9) Uani 1 1 d . . .
H26 H 0.6154 0.9575 1.0386 0.053 Uiso 1 1 calc R . .
C27 C 0.63706(9) 0.8361(4) 0.94034(17) 0.0370(8) Uani 1 1 d . . .
H27 H 0.6220 0.7386 0.9420 0.044 Uiso 1 1 calc R . .
C28 C 0.47572(11) 0.7042(6) 0.3520(2) 0.0627(11) Uani 1 1 d . . .
N1 N 0.45919(9) 0.8129(5) 0.52019(19) 0.0662(10) Uani 1 1 d . . .
N2 N 0.50592(8) 0.8120(4) 0.63761(17) 0.0575(9) Uani 1 1 d . . .
N3 N 0.66637(7) 0.7176(3) 0.81754(13) 0.0313(6) Uani 1 1 d . . .
N4 N 0.45378(10) 0.7104(6) 0.2993(2) 0.0871(12) Uani 1 1 d . . .
S1 S 0.46284(3) 0.85838(18) 0.61753(7) 0.0773(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.350(5) . ?
C1 C2 1.410(5) . ?
C1 C6 1.441(4) . ?
C2 C3 1.369(5) . ?
C2 C28 1.444(5) . ?
C3 C4 1.429(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.432(4) . ?
C5 C7 1.483(4) . ?
C6 N2 1.340(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.395(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(4) . ?
C9 C13 1.524(4) . ?
C10 N3 1.395(4) . ?
C10 C11 1.404(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C16 1.529(4) . ?
C13 C14 1.536(4) . ?
C13 C15 1.549(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.401(4) . ?
C16 C17 1.403(4) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.399(4) . ?
C20 H20 0.9300 . ?
C21 N3 1.408(4) . ?
C22 C23 1.377(4) . ?
C22 C27 1.393(4) . ?
C22 N3 1.444(4) . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N4 1.145(4) . ?
N1 S1 1.607(3) . ?
N2 S1 1.619(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
N1 C1 C2 126.3(3) . . ?
N1 C1 C6 113.8(3) . . ?
C2 C1 C6 119.9(3) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C28 122.6(3) . . ?
C1 C2 C28 118.9(3) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 123.1(3) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 116.1(3) . . ?
C4 C5 C7 122.2(3) . . ?
C6 C5 C7 121.7(3) . . ?
N2 C6 C5 126.3(3) . . ?
N2 C6 C1 112.5(3) . . ?
C5 C6 C1 121.2(3) . . ?
C8 C7 C12 116.9(3) . . ?
C8 C7 C5 121.7(3) . . ?
C12 C7 C5 121.4(3) . . ?
C9 C8 C7 124.1(3) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 C13 120.3(3) . . ?
C10 C9 C13 122.2(3) . . ?
N3 C10 C11 120.2(3) . . ?
N3 C10 C9 120.7(3) . . ?
C11 C10 C9 119.2(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C9 C13 C16 111.7(2) . . ?
C9 C13 C14 108.6(3) . . ?
C16 C13 C14 108.7(2) . . ?
C9 C13 C15 109.4(2) . . ?
C16 C13 C15 109.6(2) . . ?
C14 C13 C15 108.9(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 117.0(3) . . ?
C21 C16 C13 122.6(3) . . ?
C17 C16 C13 120.3(3) . . ?
C18 C17 C16 122.8(3) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C16 120.0(3) . . ?
C20 C21 N3 120.0(2) . . ?
C16 C21 N3 120.0(2) . . ?
C23 C22 C27 120.3(3) . . ?
C23 C22 N3 120.6(3) . . ?
C27 C22 N3 119.1(3) . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.8(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
N4 C28 C2 178.9(5) . . ?
C1 N1 S1 105.7(3) . . ?
C6 N2 S1 106.6(2) . . ?
C10 N3 C21 122.1(2) . . ?
C10 N3 C22 118.7(2) . . ?
C21 N3 C22 119.1(2) . . ?
N1 S1 N2 101.45(16) . . ?

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 -179.1(4) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
N1 C1 C2 C28 2.0(6) . . . . ?
C6 C1 C2 C28 -178.1(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C28 C2 C3 C4 177.9(4) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C3 C4 C5 C7 -178.7(3) . . . . ?
C4 C5 C6 N2 177.8(3) . . . . ?
C7 C5 C6 N2 -3.2(5) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C7 C5 C6 C1 178.5(3) . . . . ?
N1 C1 C6 N2 1.3(5) . . . . ?
C2 C1 C6 N2 -178.6(3) . . . . ?
N1 C1 C6 C5 179.8(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C4 C5 C7 C8 -35.5(5) . . . . ?
C6 C5 C7 C8 145.6(3) . . . . ?
C4 C5 C7 C12 141.6(3) . . . . ?
C6 C5 C7 C12 -37.3(4) . . . . ?
C12 C7 C8 C9 1.1(4) . . . . ?
C5 C7 C8 C9 178.3(3) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C7 C8 C9 C13 -179.0(3) . . . . ?
C8 C9 C10 N3 176.0(3) . . . . ?
C13 C9 C10 N3 -3.2(4) . . . . ?
C8 C9 C10 C11 -4.0(4) . . . . ?
C13 C9 C10 C11 176.8(3) . . . . ?
N3 C10 C11 C12 -176.5(3) . . . . ?
C9 C10 C11 C12 3.5(4) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
C5 C7 C12 C11 -178.9(3) . . . . ?
C8 C9 C13 C16 176.4(2) . . . . ?
C10 C9 C13 C16 -4.3(4) . . . . ?
C8 C9 C13 C14 -63.7(3) . . . . ?
C10 C9 C13 C14 115.5(3) . . . . ?
C8 C9 C13 C15 55.0(4) . . . . ?
C10 C9 C13 C15 -125.8(3) . . . . ?
C9 C13 C16 C21 9.6(4) . . . . ?
C14 C13 C16 C21 -110.2(3) . . . . ?
C15 C13 C16 C21 130.9(3) . . . . ?
C9 C13 C16 C17 -173.9(2) . . . . ?
C14 C13 C16 C17 66.3(3) . . . . ?
C15 C13 C16 C17 -52.6(3) . . . . ?
C21 C16 C17 C18 0.4(4) . . . . ?
C13 C16 C17 C18 -176.3(3) . . . . ?
C16 C17 C18 C19 2.4(5) . . . . ?
C17 C18 C19 C20 -2.0(5) . . . . ?
C18 C19 C20 C21 -1.1(5) . . . . ?
C19 C20 C21 C16 3.9(4) . . . . ?
C19 C20 C21 N3 -175.6(3) . . . . ?
C17 C16 C21 C20 -3.5(4) . . . . ?
C13 C16 C21 C20 173.1(3) . . . . ?
C17 C16 C21 N3 176.1(2) . . . . ?
C13 C16 C21 N3 -7.3(4) . . . . ?
C27 C22 C23 C24 0.4(5) . . . . ?
N3 C22 C23 C24 178.6(3) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
C24 C25 C26 C27 1.2(5) . . . . ?
C25 C26 C27 C22 -1.1(5) . . . . ?
C23 C22 C27 C26 0.3(5) . . . . ?
N3 C22 C27 C26 -178.0(3) . . . . ?
C3 C2 C28 N4 -147(27) . . . . ?
C1 C2 C28 N4 32(27) . . . . ?
C2 C1 N1 S1 179.0(3) . . . . ?
C6 C1 N1 S1 -0.9(4) . . . . ?
C5 C6 N2 S1 -179.4(3) . . . . ?
C1 C6 N2 S1 -1.0(4) . . . . ?
C11 C10 N3 C21 -173.6(2) . . . . ?
C9 C10 N3 C21 6.4(4) . . . . ?
C11 C10 N3 C22 3.1(4) . . . . ?
C9 C10 N3 C22 -176.9(2) . . . . ?
C20 C21 N3 C10 178.4(3) . . . . ?
C16 C21 N3 C10 -1.2(4) . . . . ?
C20 C21 N3 C22 1.7(4) . . . . ?
C16 C21 N3 C22 -177.8(3) . . . . ?
C23 C22 N3 C10 -99.4(3) . . . . ?
C27 C22 N3 C10 78.9(3) . . . . ?
C23 C22 N3 C21 77.4(3) . . . . ?
C27 C22 N3 C21 -104.4(3) . . . . ?
C1 N1 S1 N2 0.2(3) . . . . ?
C6 N2 S1 N1 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.053
