# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_23-Diphenyl-2H-azirine
_database_code_depnum_ccdc_archive 'CCDC 2380981'
loop_
_audit_author_name
_audit_author_address
'fatemeh safari'
;university illinois chicago
United States of America
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-01-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_2,3-Diphenyl-2H-azirine 
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.02 Report
RESPONSE: due to light atom
;
_vrf_PLAT097_2,3-Diphenyl-2H-azirine 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.76 eA-3  
RESPONSE: Due to elecrorin density in ring bond centre and having N in structure 
and the reason for that is that the deviation from spherical atomic density due
to bonding effects is generally not taken into account in th
refined set of model parameters.
;
_vrf_PLAT601_2,3-Diphenyl-2H-azirine 
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        124 Ang**3
RESPONSE: due to light atom
;
_vrf_PLAT934_2,3-Diphenyl-2H-azirine 
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check 
RESPONSE: due to light atom
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N'
_chemical_formula_weight         193.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_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+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   18.5963(5)
_cell_length_b                   18.5963(5)
_cell_length_c                   5.7039(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1708.27(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    278(2)
_cell_measurement_reflns_used    7064
_cell_measurement_theta_min      4.7440
_cell_measurement_theta_max      78.6490

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.505
_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      278(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22535
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.756
_diffrn_reflns_theta_max         79.395
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2436
_reflns_number_gt                1801
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    1.000

_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_structure_solution    'ShelXL (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.1334P)²] 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 661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.2165
_refine_ls_wR_factor_gt          0.1970
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.141
_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
N7 N -0.0257(2) 0.5538(2) 0.6045(9) 0.0789(12) Uani 1 1 d . . . . .
C1 C 0.1300(2) 0.6586(2) 0.6046(8) 0.0567(9) Uani 1 1 d . . . . .
C9 C 0.0441(2) 0.6112(2) 0.5369(9) 0.0631(11) Uani 1 1 d . . . . .
C2 C 0.1570(3) 0.6407(3) 0.8110(8) 0.0644(10) Uani 1 1 d . . . . .
H2 H 0.119388 0.599062 0.909806 0.077 Uiso 1 1 calc R U . . .
C10 C -0.0565(2) 0.6519(2) 0.3479(8) 0.0598(10) Uani 1 1 d . . . . .
C6 C 0.1856(2) 0.7211(3) 0.4576(8) 0.0606(10) Uani 1 1 d . . . . .
H6 H 0.167133 0.733512 0.320273 0.073 Uiso 1 1 calc R U . . .
C8 C -0.0194(3) 0.5983(3) 0.3648(9) 0.0663(11) Uani 1 1 d . . . . .
H8 H -0.021375 0.567829 0.222596 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2689(3) 0.7648(3) 0.5173(10) 0.0654(10) Uani 1 1 d . . . . .
H5 H 0.306795 0.806373 0.418989 0.078 Uiso 1 1 calc R U . . .
C3 C 0.2403(3) 0.6853(3) 0.8692(9) 0.0672(11) Uani 1 1 d . . . . .
H3 H 0.258940 0.673873 1.007925 0.081 Uiso 1 1 calc R U . . .
C4 C 0.2955(3) 0.7466(3) 0.7217(9) 0.0668(11) Uani 1 1 d . . . . .
H4 H 0.351573 0.776143 0.760856 0.080 Uiso 1 1 calc R U . . .
C15 C -0.0492(3) 0.7065(3) 0.5254(9) 0.0696(11) Uani 1 1 d . . . . .
H15 H -0.018570 0.711224 0.659310 0.083 Uiso 1 1 calc R U . . .
C11 C -0.1014(3) 0.6477(3) 0.1511(10) 0.0766(13) Uani 1 1 d . . . . .
H11 H -0.105927 0.612579 0.028825 0.092 Uiso 1 1 calc R U . . .
C14 C -0.0870(4) 0.7536(3) 0.5034(12) 0.0859(15) Uani 1 1 d . . . . .
H14 H -0.081849 0.789668 0.623415 0.103 Uiso 1 1 calc R U . . .
C13 C -0.1318(4) 0.7481(4) 0.3086(14) 0.0920(18) Uani 1 1 d . . . . .
H13 H -0.156965 0.780415 0.295346 0.110 Uiso 1 1 calc R U . . .
C12 C -0.1396(4) 0.6944(4) 0.1317(13) 0.0918(16) Uani 1 1 d . . . . .
H12 H -0.170657 0.689743 -0.001011 0.110 Uiso 1 1 calc R U . . .


_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
N7 C9 1.260(6) . ?
N7 C8 1.572(7) . ?
C1 C2 1.384(6) . ?
C1 C6 1.385(6) . ?
C1 C9 1.439(6) . ?
C9 C8 1.461(7) . ?
C2 C3 1.384(7) . ?
C2 H2 0.9300 . ?
C10 C11 1.377(7) . ?
C10 C15 1.392(6) . ?
C10 C8 1.471(6) . ?
C6 C5 1.385(6) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C5 C4 1.373(7) . ?
C5 H5 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C15 C14 1.375(7) . ?
C15 H15 0.9300 . ?
C11 C12 1.374(8) . ?
C11 H11 0.9300 . ?
C14 C13 1.362(10) . ?
C14 H14 0.9300 . ?
C13 C12 1.376(11) . ?
C13 H13 0.9300 . ?
C12 H12 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
C9 N7 C8 60.9(3) . . ?
C2 C1 C6 120.5(4) . . ?
C2 C1 C9 120.4(4) . . ?
C6 C1 C9 119.0(4) . . ?
N7 C9 C1 142.7(5) . . ?
N7 C9 C8 70.1(3) . . ?
C1 C9 C8 147.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C11 C10 C15 118.0(4) . . ?
C11 C10 C8 119.4(4) . . ?
C15 C10 C8 122.6(4) . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C9 C8 C10 123.2(4) . . ?
C9 C8 N7 48.9(3) . . ?
C10 C8 N7 118.5(4) . . ?
C9 C8 H8 116.3 . . ?
C10 C8 H8 116.3 . . ?
N7 C8 H8 116.3 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C14 C15 C10 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C14 C15 121.1(6) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?

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
C8 N7 C9 C1 177.7(7) . . . . ?
C2 C1 C9 N7 3.3(9) . . . . ?
C6 C1 C9 N7 -178.1(6) . . . . ?
C2 C1 C9 C8 179.3(6) . . . . ?
C6 C1 C9 C8 -2.1(9) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C9 C1 C2 C3 178.0(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C9 C1 C6 C5 -177.5(4) . . . . ?
N7 C9 C8 C10 100.7(5) . . . . ?
C1 C9 C8 C10 -76.8(9) . . . . ?
C1 C9 C8 N7 -177.4(8) . . . . ?
C11 C10 C8 C9 165.4(4) . . . . ?
C15 C10 C8 C9 -15.5(7) . . . . ?
C11 C10 C8 N7 -137.2(4) . . . . ?
C15 C10 C8 N7 42.0(6) . . . . ?
C9 N7 C8 C10 -110.7(5) . . . . ?
C1 C6 C5 C4 -0.7(6) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C6 C5 C4 C3 -0.1(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C11 C10 C15 C14 0.9(7) . . . . ?
C8 C10 C15 C14 -178.2(4) . . . . ?
C15 C10 C11 C12 -1.5(7) . . . . ?
C8 C10 C11 C12 177.6(5) . . . . ?
C10 C15 C14 C13 -0.3(8) . . . . ?
C15 C14 C13 C12 0.2(10) . . . . ?
C10 C11 C12 C13 1.5(9) . . . . ?
C14 C13 C12 C11 -0.8(10) . . . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.073

