# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_KB99_0m
_database_code_depnum_ccdc_archive 'CCDC 2211562'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-10-07 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N2'
_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_weight         206.24

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   18.564(10)
_cell_length_b                   5.046(2)
_cell_length_c                   11.181(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1047.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4873
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.30

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5322
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16279
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.852
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2564
_reflns_number_gt                1580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.996

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.7071P] 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_abs_structure_details 
;
 Flack x determined using 595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2564
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.3969(2) 0.0031(10) 0.5157(4) 0.0468(11) Uani 1 1 d . . . . .
C2 C 0.4223(3) -0.1897(10) 0.4418(5) 0.0586(14) Uani 1 1 d . . . . .
H2 H 0.400907 -0.215657 0.367557 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4796(3) -0.3472(10) 0.4759(6) 0.0662(15) Uani 1 1 d . . . . .
H3 H 0.496296 -0.477720 0.424115 0.079 Uiso 1 1 calc R U . . .
C4 C 0.5122(3) -0.3143(11) 0.5847(6) 0.0679(16) Uani 1 1 d . . . . .
H4 H 0.550891 -0.420725 0.606696 0.081 Uiso 1 1 calc R U . . .
C5 C 0.4869(3) -0.1209(11) 0.6613(5) 0.0673(15) Uani 1 1 d . . . . .
H5 H 0.508299 -0.097159 0.735742 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4291(3) 0.0389(10) 0.6267(5) 0.0598(14) Uani 1 1 d . . . . .
H6 H 0.412092 0.169610 0.678095 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3351(2) 0.1708(10) 0.4800(4) 0.0440(11) Uani 1 1 d . . . . .
C8 C 0.2533(2) 0.5002(8) 0.5202(4) 0.0404(10) Uani 1 1 d . . . . .
C9 C 0.2204(2) 0.4581(9) 0.4087(4) 0.0428(10) Uani 1 1 d . . . . .
C10 C 0.2515(3) 0.2624(9) 0.3377(4) 0.0528(11) Uani 1 1 d . . . . .
H10 H 0.230858 0.230047 0.263352 0.063 Uiso 1 1 calc R U . . .
C11 C 0.2263(2) 0.6960(9) 0.5954(5) 0.0500(12) Uani 1 1 d . . . . .
H11 H 0.247911 0.726535 0.669093 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1686(3) 0.8426(10) 0.5617(5) 0.0536(12) Uani 1 1 d . . . . .
H12 H 0.150956 0.972710 0.612831 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1354(2) 0.8009(11) 0.4515(5) 0.0530(13) Uani 1 1 d . . . . .
H13 H 0.095652 0.902570 0.430034 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1606(2) 0.6127(9) 0.3749(4) 0.0493(12) Uani 1 1 d . . . . .
H14 H 0.138517 0.586377 0.301204 0.059 Uiso 1 1 calc R U . . .
N1 N 0.3117(2) 0.3486(7) 0.5551(3) 0.0453(9) Uani 1 1 d . . . . .
N2 N 0.3081(2) 0.1192(8) 0.3684(3) 0.0502(10) 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
C1 C2 1.360(7) . ?
C1 C6 1.389(7) . ?
C1 C7 1.481(6) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.304(5) . ?
C7 N2 1.370(6) . ?
C8 N1 1.383(5) . ?
C8 C11 1.390(6) . ?
C8 C9 1.404(6) . ?
C9 C10 1.392(6) . ?
C9 C14 1.409(6) . ?
C10 N2 1.320(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(7) . ?
C13 H13 0.9300 . ?
C14 H14 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
C2 C1 C6 119.1(5) . . ?
C2 C1 C7 120.9(4) . . ?
C6 C1 C7 120.0(4) . . ?
C1 C2 C3 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.2(5) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 N2 126.6(4) . . ?
N1 C7 C1 118.6(4) . . ?
N2 C7 C1 114.9(4) . . ?
N1 C8 C11 120.3(4) . . ?
N1 C8 C9 120.5(4) . . ?
C11 C8 C9 119.2(4) . . ?
C10 C9 C8 115.7(4) . . ?
C10 C9 C14 124.5(4) . . ?
C8 C9 C14 119.8(4) . . ?
N2 C10 C9 124.8(4) . . ?
N2 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C12 C11 C8 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C8 C11 H11 119.8 . . ?
C11 C12 C13 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 119.3(5) . . ?
C13 C14 H14 120.4 . . ?
C9 C14 H14 120.4 . . ?
C7 N1 C8 117.4(4) . . ?
C10 N2 C7 115.1(4) . . ?

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
C6 C1 C2 C3 -0.4(7) . . . . ?
C7 C1 C2 C3 -179.4(5) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C7 C1 C6 C5 179.3(4) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C2 C1 C7 N1 178.4(4) . . . . ?
C6 C1 C7 N1 -0.6(6) . . . . ?
C2 C1 C7 N2 -1.5(6) . . . . ?
C6 C1 C7 N2 179.5(4) . . . . ?
N1 C8 C9 C10 -1.3(6) . . . . ?
C11 C8 C9 C10 178.7(4) . . . . ?
N1 C8 C9 C14 179.4(4) . . . . ?
C11 C8 C9 C14 -0.5(6) . . . . ?
C8 C9 C10 N2 0.0(7) . . . . ?
C14 C9 C10 N2 179.2(5) . . . . ?
N1 C8 C11 C12 -179.3(4) . . . . ?
C9 C8 C11 C12 0.6(6) . . . . ?
C8 C11 C12 C13 -0.2(7) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C12 C13 C14 C9 0.5(7) . . . . ?
C10 C9 C14 C13 -179.2(4) . . . . ?
C8 C9 C14 C13 -0.1(6) . . . . ?
N2 C7 N1 C8 0.7(6) . . . . ?
C1 C7 N1 C8 -179.2(4) . . . . ?
C11 C8 N1 C7 -179.0(4) . . . . ?
C9 C8 N1 C7 1.1(5) . . . . ?
C9 C10 N2 C7 1.5(7) . . . . ?
N1 C7 N2 C10 -1.9(6) . . . . ?
C1 C7 N2 C10 177.9(4) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045



