# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ark12
_database_code_depnum_ccdc_archive 'CCDC 1915543'
loop_
_audit_author_name
_audit_author_address
'Arkalekha Mandal' 'IISER Bhopal'
_audit_update_record             
;
2019-05-12 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H15 N5'
_chemical_formula_weight         421.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7858(2)
_cell_length_b                   8.7123(2)
_cell_length_c                   18.1329(4)
_cell_angle_alpha                99.099(2)
_cell_angle_beta                 91.152(2)
_cell_angle_gamma                97.907(2)
_cell_volume                     1047.50(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4215
_cell_measurement_theta_min      4.94
_cell_measurement_theta_max      75.49

_exptl_crystal_description       clear
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18660
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.94
_diffrn_reflns_theta_max         75.49
_reflns_number_total             4215
_reflns_number_gt                3240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0340P)²+4.3500P] 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         4215
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.1199
_refine_ls_wR_factor_ref         0.2819
_refine_ls_wR_factor_gt          0.2771
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C15 C 0.3377(6) 0.2872(5) 0.2135(3) 0.0474(11) Uani 1 1 d . . .
C17 C 0.8454(6) 0.3696(5) 0.1948(3) 0.0446(11) Uani 1 1 d . . .
C18 C 0.8658(6) 0.4576(5) 0.2697(3) 0.0481(11) Uani 1 1 d . . .
H18 H 0.8793 0.5667 0.2767 0.058 Uiso 1 1 calc R . .
C22 C 0.8282(6) 0.2023(6) 0.1865(3) 0.0479(11) Uani 1 1 d . . .
H22 H 0.8200 0.1437 0.1387 0.057 Uiso 1 1 calc R . .
N3 N 0.8354(8) 0.7409(6) 0.1440(3) 0.0765(15) Uani 1 1 d . . .
C16 C 0.3389(6) 0.2475(6) 0.2865(3) 0.0483(11) Uani 1 1 d . . .
C20 C 0.8426(6) 0.2163(6) 0.3205(3) 0.0466(11) Uani 1 1 d . . .
C21 C 0.8236(6) 0.1278(6) 0.2457(3) 0.0491(11) Uani 1 1 d . . .
H21 H 0.8082 0.0187 0.2386 0.059 Uiso 1 1 calc R . .
C19 C 0.8654(6) 0.3839(6) 0.3292(3) 0.0496(11) Uani 1 1 d . . .
H19 H 0.8801 0.4428 0.3770 0.060 Uiso 1 1 calc R . .
C23 C 0.8413(7) 0.4452(6) 0.1335(3) 0.0494(11) Uani 1 1 d . . .
C24 C 0.8351(7) 0.1388(6) 0.3814(3) 0.0535(12) Uani 1 1 d . . .
N2 N 0.8115(8) 0.2915(7) -0.0003(3) 0.0803(15) Uani 1 1 d . . .
C14 C 0.3085(7) 0.1693(6) 0.1507(3) 0.0539(12) Uani 1 1 d . . .
C26 C 0.8409(7) 0.6099(7) 0.1401(3) 0.0551(12) Uani 1 1 d . . .
C25 C 0.8252(8) 0.3600(6) 0.0588(3) 0.0566(13) Uani 1 1 d . . .
C11 C 0.3096(7) 0.0883(7) 0.2957(3) 0.0584(14) Uani 1 1 d . . .
C5 C 0.3968(7) 0.5648(6) 0.2736(4) 0.0673(17) Uani 1 1 d . . .
H5 H 0.4177 0.6708 0.2696 0.081 Uiso 1 1 calc R . .
C7 C 0.3650(7) 0.3661(7) 0.3514(4) 0.0663(16) Uani 1 1 d . . .
C12 C 0.2782(7) -0.0290(6) 0.2292(4) 0.0651(16) Uani 1 1 d . . .
H12 H 0.2571 -0.1348 0.2337 0.078 Uiso 1 1 calc R . .
C27 C 0.8106(8) -0.0278(7) 0.3735(3) 0.0626(14) Uani 1 1 d . . .
C13 C 0.2789(8) 0.0117(7) 0.1611(4) 0.0656(15) Uani 1 1 d . . .
H13 H 0.2591 -0.0668 0.1194 0.079 Uiso 1 1 calc R . .
C4 C 0.3660(6) 0.4509(6) 0.2071(4) 0.0598(14) Uani 1 1 d . . .
N5 N 0.8665(9) 0.2888(8) 0.5164(3) 0.0937(19) Uani 1 1 d . . .
C28 C 0.8532(8) 0.2223(8) 0.4564(3) 0.0646(15) Uani 1 1 d . . .
C2 C 0.3291(8) 0.3752(7) 0.0747(4) 0.0674(15) Uani 1 1 d . . .
H2 H 0.3257 0.4060 0.0279 0.081 Uiso 1 1 calc R . .
N4 N 0.7925(9) -0.1615(7) 0.3665(4) 0.0916(18) Uani 1 1 d . . .
C1 C 0.3041(8) 0.2183(8) 0.0784(4) 0.0687(15) Uani 1 1 d . . .
C8 C 0.3596(8) 0.3183(10) 0.4233(4) 0.0776(19) Uani 1 1 d . . .
H8 H 0.3737 0.3928 0.4665 0.093 Uiso 1 1 calc R . .
C6 C 0.3964(8) 0.5228(8) 0.3425(5) 0.080(2) Uani 1 1 d . . .
H6 H 0.4175 0.6005 0.3845 0.096 Uiso 1 1 calc R . .
C3 C 0.3591(8) 0.4897(7) 0.1371(4) 0.0761(19) Uani 1 1 d . . .
H3 H 0.3749 0.5950 0.1315 0.091 Uiso 1 1 calc R . .
C9 C 0.3328(9) 0.1587(11) 0.4275(4) 0.089(2) Uani 1 1 d . . .
H9 H 0.3322 0.1289 0.4746 0.107 Uiso 1 1 calc R . .
N1 N 0.2745(10) 0.1098(8) 0.0162(4) 0.110(2) Uani 1 1 d . . .
H1A H 0.2710 0.1387 -0.0270 0.132 Uiso 1 1 calc R . .
H1B H 0.2591 0.0116 0.0195 0.132 Uiso 1 1 calc R . .
C10 C 0.3080(8) 0.0459(9) 0.3674(4) 0.0799(19) Uani 1 1 d . . .
H10 H 0.2898 -0.0593 0.3729 0.096 Uiso 1 1 calc R . .


_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
C15 C14 1.399(7) . ?
C15 C16 1.420(7) . ?
C15 C4 1.436(7) . ?
C17 C23 1.380(7) . ?
C17 C22 1.430(6) . ?
C17 C18 1.445(6) . ?
C18 C19 1.340(7) . ?
C18 H18 0.9300 . ?
C22 C21 1.338(7) . ?
C22 H22 0.9300 . ?
N3 C26 1.139(7) . ?
C16 C11 1.410(7) . ?
C16 C7 1.428(7) . ?
C20 C24 1.381(7) . ?
C20 C19 1.430(7) . ?
C20 C21 1.445(7) . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C23 C26 1.421(7) . ?
C23 C25 1.431(7) . ?
C24 C27 1.422(8) . ?
C24 C28 1.431(8) . ?
N2 C25 1.138(7) . ?
C14 C13 1.403(7) . ?
C14 C1 1.443(8) . ?
C11 C10 1.406(8) . ?
C11 C12 1.445(8) . ?
C5 C6 1.355(9) . ?
C5 C4 1.427(8) . ?
C5 H5 0.9300 . ?
C7 C6 1.388(9) . ?
C7 C8 1.429(9) . ?
C12 C13 1.336(8) . ?
C12 H12 0.9300 . ?
C27 N4 1.141(7) . ?
C13 H13 0.9300 . ?
C4 C3 1.366(9) . ?
N5 C28 1.143(7) . ?
C2 C1 1.367(8) . ?
C2 C3 1.377(9) . ?
C2 H2 0.9300 . ?
C1 N1 1.344(8) . ?
C8 C9 1.393(10) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C9 C10 1.338(10) . ?
C9 H9 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C10 H10 0.9300 . ?

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
C14 C15 C16 120.3(4) . . ?
C14 C15 C4 121.9(5) . . ?
C16 C15 C4 117.7(5) . . ?
C23 C17 C22 121.4(4) . . ?
C23 C17 C18 120.8(4) . . ?
C22 C17 C18 117.8(4) . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C21 C22 C17 121.7(5) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 C7 119.0(5) . . ?
C15 C16 C7 121.2(5) . . ?
C24 C20 C19 121.7(5) . . ?
C24 C20 C21 120.0(5) . . ?
C19 C20 C21 118.3(5) . . ?
C22 C21 C20 120.3(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C18 C19 C20 121.1(5) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C17 C23 C26 122.6(5) . . ?
C17 C23 C25 121.5(4) . . ?
C26 C23 C25 115.8(5) . . ?
C20 C24 C27 122.2(5) . . ?
C20 C24 C28 121.7(5) . . ?
C27 C24 C28 116.1(5) . . ?
C15 C14 C13 118.9(5) . . ?
C15 C14 C1 117.4(5) . . ?
C13 C14 C1 123.7(5) . . ?
N3 C26 C23 177.9(6) . . ?
N2 C25 C23 179.5(7) . . ?
C10 C11 C16 120.9(6) . . ?
C10 C11 C12 121.3(6) . . ?
C16 C11 C12 117.7(5) . . ?
C6 C5 C4 121.9(5) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C6 C7 C16 119.1(6) . . ?
C6 C7 C8 122.5(6) . . ?
C16 C7 C8 118.4(6) . . ?
C13 C12 C11 121.2(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N4 C27 C24 179.2(7) . . ?
C12 C13 C14 122.0(5) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C3 C4 C5 123.2(6) . . ?
C3 C4 C15 117.9(6) . . ?
C5 C4 C15 118.9(6) . . ?
N5 C28 C24 179.6(7) . . ?
C1 C2 C3 122.9(6) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
N1 C1 C2 121.3(7) . . ?
N1 C1 C14 119.8(6) . . ?
C2 C1 C14 118.9(6) . . ?
C9 C8 C7 119.0(6) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C5 C6 C7 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C10 C9 C8 123.3(7) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 C10 C11 119.3(7) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        75.49
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.059
