# 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_nf0123010a_sqd
_database_code_depnum_ccdc_archive 'CCDC 1454694'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2017-01-12 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            'C36 H30 N4 S'
_chemical_formula_weight         550.70

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   26.456(9)
_cell_length_b                   7.923(2)
_cell_length_c                   17.551(7)
_cell_angle_alpha                90
_cell_angle_beta                 120.844(7)
_cell_angle_gamma                90
_cell_volume                     3158.6(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4465
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10403
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3050
_reflns_number_gt                2360
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1496P)²+2.2543P] 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         3050
_refine_ls_number_parameters     220
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2601
_refine_ls_wR_factor_gt          0.2490
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
C12 C 0.92123(13) 0.9551(5) 0.75479(19) 0.0671(9) Uani 1 1 d . . . . .
H12 H 0.9505 1.0195 0.8004 0.081 Uiso 1 1 calc R U . . .
C6 C 0.81536(10) 0.6454(3) 0.81299(16) 0.0453(6) Uani 1 1 d . . . . .
C1 C 0.86158(10) 0.7413(3) 0.87948(15) 0.0452(6) Uani 1 1 d . . . . .
C13 C 0.88939(11) 0.8395(4) 0.77354(15) 0.0497(7) Uani 1 1 d . . . . .
C8 C 0.84508(10) 0.7423(3) 0.70596(16) 0.0471(6) Uani 1 1 d . . . . .
C7 C 0.81300(11) 0.6058(3) 0.72632(16) 0.0511(7) Uani 1 1 d . . . . .
C2 C 0.86754(13) 0.7575(4) 0.96251(17) 0.0569(7) Uani 1 1 d . . . . .
H2 H 0.8992 0.8178 1.0068 0.068 Uiso 1 1 calc R U . . .
N1 N 0.90214(11) 0.8190(4) 0.86181(14) 0.0648(8) Uani 1 1 d . U . . .
C9 C 0.83510(13) 0.7657(4) 0.62025(17) 0.0656(8) Uani 1 1 d . . . . .
H9 H 0.8059 0.7023 0.5741 0.079 Uiso 1 1 calc R U . . .
C16 C 0.95113(14) 0.9088(5) 0.93134(18) 0.0619(9) Uani 1 1 d . U . . .
C5 C 0.77524(13) 0.5775(4) 0.8328(2) 0.0654(8) Uani 1 1 d . . . . .
H5 H 0.7435 0.5167 0.7892 0.079 Uiso 1 1 calc R U . . .
C3 C 0.82738(15) 0.6857(4) 0.9801(2) 0.0688(9) Uani 1 1 d . . . . .
H3 H 0.8317 0.6971 1.0359 0.083 Uiso 1 1 calc R U . . .
C10 C 0.86670(14) 0.8785(5) 0.60152(19) 0.0754(10) Uani 1 1 d . . . . .
H10 H 0.8591 0.8896 0.5438 0.090 Uiso 1 1 calc R U . . .
C11 C 0.90988(15) 0.9752(5) 0.6693(2) 0.0760(10) Uani 1 1 d . . . . .
H11 H 0.9311 1.0533 0.6573 0.091 Uiso 1 1 calc R U . . .
C14 C 0.74938(14) 0.5868(6) 0.6495(2) 0.0854(12) Uani 1 1 d . . . . .
H14A H 0.7297 0.5031 0.6644 0.128 Uiso 1 1 calc R U . . .
H14B H 0.7493 0.5527 0.5970 0.128 Uiso 1 1 calc R U . . .
H14C H 0.7293 0.6929 0.6390 0.128 Uiso 1 1 calc R U . . .
C4 C 0.78058(16) 0.5965(5) 0.9145(3) 0.0767(10) Uani 1 1 d . . . . .
H4 H 0.7527 0.5493 0.9254 0.092 Uiso 1 1 calc R U . . .
C15 C 0.8449(2) 0.4365(4) 0.7379(3) 0.0866(11) Uani 1 1 d . . . . .
H15A H 0.8850 0.4457 0.7858 0.130 Uiso 1 1 calc R U . . .
H15B H 0.8443 0.4093 0.6841 0.130 Uiso 1 1 calc R U . . .
H15C H 0.8254 0.3491 0.7510 0.130 Uiso 1 1 calc R U . . .
C17A C 1.0021(11) 0.852(2) 0.9763(13) 0.047(4) Uani 0.520(4) 1 d . . P A 1
C18A C 1.0480(8) 0.946(2) 1.0447(13) 0.056(4) Uani 0.520(4) 1 d . . P A 1
S1 S 1.08241(8) 0.6661(2) 1.03714(12) 0.0767(7) Uani 0.520(4) 1 d . . P A 1
N3 N 1.0993(3) 0.8467(7) 1.0843(3) 0.0629(13) Uani 0.520(4) 1 d . . P A 1
N2 N 1.0139(2) 0.6907(6) 0.9651(3) 0.0639(13) Uani 0.520(4) 1 d . . P A 1
C17 C 1.0083(12) 0.810(2) 0.9833(16) 0.057(4) Uani 0.520(4) 1 d . U P A 2
H17 H 1.0112 0.6965 0.9730 0.068 Uiso 0.480(4) 1 calc R U P A 2
C18 C 1.0590(6) 0.909(2) 1.0517(10) 0.038(3) Uani 0.480(4) 1 d . . P A 2
H18 H 1.0962 0.8606 1.0837 0.045 Uiso 0.480(4) 1 calc R U P A 2


_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
C12 C11 1.381(4) . ?
C12 C13 1.393(4) . ?
C6 C5 1.384(4) . ?
C6 C1 1.404(3) . ?
C6 C7 1.523(4) . ?
C1 C2 1.389(4) . ?
C1 N1 1.402(3) . ?
C13 C8 1.396(3) . ?
C13 N1 1.416(3) . ?
C8 C9 1.400(4) . ?
C8 C7 1.526(4) . ?
C7 C14 1.532(4) . ?
C7 C15 1.543(5) . ?
C2 C3 1.372(4) . ?
N1 C16 1.433(3) . ?
C9 C10 1.374(5) . ?
C16 C18A 1.221(19) 5_777 ?
C16 C17A 1.25(2) . ?
C16 C17 1.52(2) . ?
C16 C18 1.526(15) 5_777 ?
C5 C4 1.374(5) . ?
C3 C4 1.377(5) . ?
C10 C11 1.383(5) . ?
C17A N2 1.350(17) . ?
C17A C18A 1.41(3) . ?
C17A C18A 1.99(3) 5_777 ?
C18A C16 1.221(19) 5_777 ?
C18A N3 1.406(14) . ?
C18A C17A 1.99(3) 5_777 ?
S1 N3 1.598(5) . ?
S1 N2 1.604(6) . ?
C17 C18 1.48(3) . ?
C18 C16 1.526(15) 5_777 ?

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
C11 C12 C13 120.8(3) . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 C7 121.8(2) . . ?
C1 C6 C7 120.9(2) . . ?
C2 C1 N1 120.2(2) . . ?
C2 C1 C6 120.3(2) . . ?
N1 C1 C6 119.5(2) . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 N1 120.0(2) . . ?
C8 C13 N1 119.4(2) . . ?
C13 C8 C9 117.0(2) . . ?
C13 C8 C7 121.2(2) . . ?
C9 C8 C7 121.6(2) . . ?
C6 C7 C8 110.21(19) . . ?
C6 C7 C14 111.3(2) . . ?
C8 C7 C14 110.8(2) . . ?
C6 C7 C15 108.0(2) . . ?
C8 C7 C15 108.3(2) . . ?
C14 C7 C15 108.1(3) . . ?
C3 C2 C1 120.8(3) . . ?
C1 N1 C13 120.8(2) . . ?
C1 N1 C16 119.3(2) . . ?
C13 N1 C16 118.6(2) . . ?
C10 C9 C8 122.7(3) . . ?
C18A C16 C17A 107.5(12) 5_777 . ?
C18A C16 N1 127.6(9) 5_777 . ?
C17A C16 N1 124.8(8) . . ?
N1 C16 C17 116.3(9) . . ?
N1 C16 C18 117.6(6) . 5_777 ?
C17 C16 C18 126.1(10) . 5_777 ?
C4 C5 C6 122.5(3) . . ?
C2 C3 C4 119.5(3) . . ?
C9 C10 C11 119.4(3) . . ?
C12 C11 C10 119.6(3) . . ?
C5 C4 C3 119.7(3) . . ?
C16 C17A N2 120.4(15) . . ?
C16 C17A C18A 121.8(15) . . ?
N2 C17A C18A 117.6(18) . . ?
C16 C17A C18A 35.8(7) . 5_777 ?
N2 C17A C18A 156.1(16) . 5_777 ?
C18A C17A C18A 86.1(12) . 5_777 ?
C16 C18A N3 121.0(14) 5_777 . ?
C16 C18A C17A 130.5(16) 5_777 . ?
N3 C18A C17A 108.4(13) . . ?
C16 C18A C17A 36.7(8) 5_777 5_777 ?
N3 C18A C17A 157.6(13) . 5_777 ?
C17A C18A C17A 93.9(12) . 5_777 ?
N3 S1 N2 101.7(3) . . ?
C18A N3 S1 107.6(8) . . ?
C17A N2 S1 104.6(10) . . ?
C18 C17 C16 115.0(14) . . ?
C17 C18 C16 118.7(12) . 5_777 ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.118



