# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_TCmCN
_database_code_depnum_ccdc_archive 'CCDC 2285795'
loop_
_audit_author_name
_audit_author_address
'Anirban Karmakar'
;Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H15 N9 O3'
_chemical_formula_weight         585.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.8757(6)
_cell_length_b                   23.8757(6)
_cell_length_c                   17.6972(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8736.7(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3562
_cell_measurement_theta_min      3.2890
_cell_measurement_theta_max      66.4410

_exptl_crystal_description       Plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             3600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.748
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9227
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.287
_diffrn_reflns_theta_max         67.091
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             3327
_reflns_number_gt                2656
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1308P)²+7.4086P] 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         3327
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1993
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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_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
O7 O 0.56728(8) 0.35056(8) 0.42674(10) 0.0640(5) Uani 1 1 d . . . . .
N3 N 0.67745(9) 0.39546(9) 0.42708(9) 0.0522(5) Uani 1 1 d . . . . .
O22 O 0.88355(9) 0.98361(9) 0.28874(11) 0.0758(6) Uani 1 1 d . . . . .
N6 N 0.94837(11) 0.93798(11) 0.28949(11) 0.0637(6) Uani 1 1 d . . . . .
C11 C 0.61933(10) 0.34349(10) 0.42726(11) 0.0499(5) Uani 1 1 d . . . . .
C1 C 0.57637(11) 0.41353(11) 0.42877(14) 0.0588(6) Uani 1 1 d . . . . .
C22 C 0.94283(12) 0.99034(13) 0.28990(12) 0.0609(6) Uani 1 1 d . . . . .
C3 C 0.58587(12) 0.50194(12) 0.50171(14) 0.0624(6) Uani 1 1 d . . . . .
C2 C 0.58156(13) 0.44164(12) 0.49749(14) 0.0638(6) Uani 1 1 d . . . . .
H2 H 0.5822 0.4206 0.5414 0.077 Uiso 1 1 calc R U . . .
C14 C 0.82912(13) 0.92156(14) 0.29787(15) 0.0696(7) Uani 1 1 d . . . . .
C6 C 0.57495(13) 0.44206(14) 0.36263(14) 0.0691(7) Uani 1 1 d . . . . .
H6 H 0.5707 0.4217 0.3165 0.083 Uiso 1 1 calc R U . . .
C4 C 0.58518(13) 0.53189(13) 0.43436(15) 0.0698(7) Uani 1 1 d . . . . .
H4 H 0.5883 0.5723 0.4356 0.084 Uiso 1 1 calc R U . . .
C5 C 0.57998(16) 0.50214(15) 0.36638(15) 0.0768(8) Uani 1 1 d . . . . .
H5 H 0.5798 0.5229 0.3219 0.092 Uiso 1 1 calc R U . . .
C13 C 0.81487(14) 0.89540(15) 0.36904(16) 0.0735(7) Uani 1 1 d . . . . .
H13 H 0.8421 0.9172 0.4093 0.088 Uiso 1 1 calc R U . . .
C7 C 0.58967(15) 0.52724(15) 0.57722(16) 0.0767(7) Uani 1 1 d . . . . .
H7 H 0.5919 0.5017 0.6155 0.092 Uiso 1 1 calc R U . . .
C8 C 0.59055(14) 0.58056(14) 0.60167(16) 0.0758(7) Uani 1 1 d . . . . .
C12 C 0.75911(14) 0.83578(15) 0.38043(17) 0.0765(7) Uani 1 1 d . . . . .
C10 C 0.59024(16) 0.62919(17) 0.55498(19) 0.0819(8) Uani 1 1 d . . . . .
N1 N 0.5906(2) 0.66975(18) 0.5205(2) 0.1141(11) Uani 1 1 d . . . . .
C15 C 0.79118(17) 0.89191(18) 0.23685(18) 0.0868(9) Uani 1 1 d . . . . .
H15 H 0.8019 0.9108 0.1892 0.104 Uiso 1 1 calc R U . . .
C17 C 0.72089(16) 0.80533(17) 0.3190(2) 0.0883(9) Uani 1 1 d . . . . .
H17 H 0.6838 0.7653 0.3255 0.106 Uiso 1 1 calc R U . . .
C19 C 0.76419(19) 0.82442(18) 0.52253(19) 0.0912(9) Uani 1 1 d . . . . .
C18 C 0.74071(17) 0.80268(18) 0.4541(2) 0.0914(9) Uani 1 1 d . . . . .
H18 H 0.7074 0.7599 0.4524 0.110 Uiso 1 1 calc R U . . .
C16 C 0.73590(18) 0.8324(2) 0.2481(2) 0.0990(11) Uani 1 1 d . . . . .
H16 H 0.7089 0.8107 0.2076 0.119 Uiso 1 1 calc R U . . .
N2 N 0.5917(2) 0.5977(2) 0.7454(2) 0.1328(14) Uani 1 1 d . . . . .
C9 C 0.5914(2) 0.59104(18) 0.6816(2) 0.0960(10) Uani 1 1 d . . . . .
N4 N 0.7266(2) 0.7494(2) 0.6388(2) 0.1384(15) Uani 1 1 d . . . . .
C20 C 0.7424(2) 0.7815(2) 0.5871(2) 0.1073(12) Uani 1 1 d . . . . .
C21 C 0.8099(3) 0.8885(2) 0.5404(2) 0.1310(18) Uani 1 1 d . . . . .
N5 N 0.8474(5) 0.9404(2) 0.5563(3) 0.238(4) 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
O7 C11 1.335(3) . ?
O7 C1 1.408(3) . ?
N3 C11 1.320(3) . ?
N3 C11 1.327(3) 3_665 ?
O22 C22 1.342(3) . ?
O22 C14 1.409(3) . ?
N6 C22 1.321(3) . ?
N6 C22 1.324(3) 2_765 ?
C11 N3 1.327(3) 2_655 ?
C1 C6 1.363(4) . ?
C1 C2 1.364(4) . ?
C22 N6 1.324(3) 3_675 ?
C3 C2 1.393(4) . ?
C3 C4 1.394(4) . ?
C3 C7 1.451(4) . ?
C2 H2 0.9300 . ?
C14 C15 1.359(4) . ?
C14 C13 1.371(4) . ?
C6 C5 1.380(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C13 C12 1.394(4) . ?
C13 H13 0.9300 . ?
C7 C8 1.335(4) . ?
C7 H7 0.9300 . ?
C8 C10 1.428(5) . ?
C8 C9 1.434(4) . ?
C12 C17 1.371(5) . ?
C12 C18 1.473(5) . ?
C10 N1 1.142(5) . ?
C15 C16 1.388(5) . ?
C15 H15 0.9300 . ?
C17 C16 1.374(5) . ?
C17 H17 0.9300 . ?
C19 C18 1.326(5) . ?
C19 C21 1.401(6) . ?
C19 C20 1.447(5) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
N2 C9 1.141(4) . ?
N4 C20 1.129(5) . ?
C21 N5 1.142(7) . ?

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 O7 C1 118.59(17) . . ?
C11 N3 C11 112.2(2) . 3_665 ?
C22 O22 C14 119.2(2) . . ?
C22 N6 C22 111.9(3) . 2_765 ?
N3 C11 N3 127.8(2) . 2_655 ?
N3 C11 O7 119.24(19) . . ?
N3 C11 O7 112.97(19) 2_655 . ?
C6 C1 C2 122.6(2) . . ?
C6 C1 O7 118.9(2) . . ?
C2 C1 O7 118.4(2) . . ?
N6 C22 N6 128.1(3) . 3_675 ?
N6 C22 O22 119.0(2) . . ?
N6 C22 O22 112.9(2) 3_675 . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C7 115.9(2) . . ?
C4 C3 C7 126.0(2) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C15 C14 C13 122.9(3) . . ?
C15 C14 O22 118.7(3) . . ?
C13 C14 O22 118.2(2) . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C8 C7 C3 131.6(3) . . ?
C8 C7 H7 114.2 . . ?
C3 C7 H7 114.2 . . ?
C7 C8 C10 125.7(3) . . ?
C7 C8 C9 118.6(3) . . ?
C10 C8 C9 115.7(3) . . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C18 118.4(3) . . ?
C13 C12 C18 123.5(3) . . ?
N1 C10 C8 176.9(3) . . ?
C14 C15 C16 117.7(3) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C16 C17 C12 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C18 C19 C21 125.4(3) . . ?
C18 C19 C20 120.8(4) . . ?
C21 C19 C20 113.7(3) . . ?
C19 C18 C12 130.1(3) . . ?
C19 C18 H18 115.0 . . ?
C12 C18 H18 115.0 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N2 C9 C8 178.1(4) . . ?
N4 C20 C19 178.1(6) . . ?
N5 C21 C19 178.7(5) . . ?

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
C11 N3 C11 N3 -0.5(4) 3_665 . . 2_655 ?
C11 N3 C11 O7 -179.67(11) 3_665 . . . ?
C1 O7 C11 N3 -2.3(3) . . . . ?
C1 O7 C11 N3 178.44(18) . . . 2_655 ?
C11 O7 C1 C6 97.1(3) . . . . ?
C11 O7 C1 C2 -87.6(3) . . . . ?
C22 N6 C22 N6 1.1(4) 2_765 . . 3_675 ?
C22 N6 C22 O22 179.29(12) 2_765 . . . ?
C14 O22 C22 N6 8.9(3) . . . . ?
C14 O22 C22 N6 -172.7(2) . . . 3_675 ?
C6 C1 C2 C3 -0.2(4) . . . . ?
O7 C1 C2 C3 -175.4(2) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
C7 C3 C2 C1 178.6(2) . . . . ?
C22 O22 C14 C15 -107.4(3) . . . . ?
C22 O22 C14 C13 76.2(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
O7 C1 C6 C5 176.1(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C7 C3 C4 C5 -178.5(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C15 C14 C13 C12 -0.1(5) . . . . ?
O22 C14 C13 C12 176.2(3) . . . . ?
C2 C3 C7 C8 -175.7(3) . . . . ?
C4 C3 C7 C8 3.2(5) . . . . ?
C3 C7 C8 C10 -2.6(6) . . . . ?
C3 C7 C8 C9 176.9(3) . . . . ?
C14 C13 C12 C17 0.6(4) . . . . ?
C14 C13 C12 C18 177.9(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
O22 C14 C15 C16 -176.5(3) . . . . ?
C13 C12 C17 C16 -0.8(5) . . . . ?
C18 C12 C17 C16 -178.2(3) . . . . ?
C21 C19 C18 C12 6.3(7) . . . . ?
C20 C19 C18 C12 -174.7(3) . . . . ?
C17 C12 C18 C19 -170.6(4) . . . . ?
C13 C12 C18 C19 12.1(6) . . . . ?
C12 C17 C16 C15 0.4(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

