# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_exp_1263_ak_dsn-892_20221107
_database_code_depnum_ccdc_archive 'CCDC 2294834'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;Department of Chemistry, Birla Institute of Technology and Science Pilani, Hyderabad Campus
India
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2022-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 N2 O'
_chemical_formula_sum            'C16 H10 N2 O'
_chemical_formula_weight         246.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H10 N2 O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0807(2)
_cell_length_b                   11.4488(3)
_cell_length_c                   13.0502(4)
_cell_angle_alpha                75.453(2)
_cell_angle_beta                 79.894(2)
_cell_angle_gamma                79.458(2)
_cell_volume                     1138.21(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      78.9640
_cell_measurement_theta_min      4.7020
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.868
_diffrn_reflns_theta_min         4.032
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -37.00   0.50    2.16    --    0.00 -37.00 120.00  104
  2  ω     56.00  86.00   0.50    2.16    --    0.00  37.00  90.00   60
  3  ω    -17.00  44.00   0.50    2.16    --    0.00  37.00  90.00  122
  4  ω    -86.00  16.00   0.50    2.16    --    0.00 -37.00-150.00  204
  5  ω    -31.00  -5.00   0.50    2.16    --    0.00 -37.00 120.00   52
  6  ω    -24.00  29.00   0.50    2.16    --    0.00 -77.00  90.00  106
  7  ω     54.00 123.00   0.50    8.65    --  107.20 -30.00 -30.00  138
  8  ω    102.00 128.00   0.50    8.65    --  107.20  30.00 -60.00   52
  9  ω     18.00  44.00   0.50    8.65    --  107.20 -30.00 -30.00   52
 10  ω     90.00 131.00   0.50    8.65    --  107.20 -82.00 -60.00   82
 11  ω     39.00 102.00   0.50    8.65    --  107.20 -82.00-180.00  126
 12  ω    141.00 197.00   0.50    8.65    --  107.20  30.00 -60.00  112
 13  ω     39.00  75.00   0.50    8.65    --  107.20 -82.00 120.00   72
 14  ω     94.00 132.00   0.50    8.65    --  107.20 -82.00 120.00   76
 15  ω     22.00  56.00   0.50    8.65    --  107.20 -82.00 -60.00   68
 16  ω     92.00 117.00   0.50    8.65    --  107.20 -45.00  60.00   50
 17  ω     99.00 140.00   0.50    8.65    --  107.20 -82.00   0.00   82
 18  ω     43.00  81.00   0.50    8.65    --  107.20 -82.00   0.00   76
 19  ω     18.00  54.00   0.50    8.65    --  107.20 -61.00-120.00   72
 20  ω     65.00 109.00   0.50    8.65    --  107.20 -61.00-120.00   88
 21  ω     18.00 129.00   0.50    8.65    --  107.20 -15.00 -30.00  222
 22  ω     99.00 124.00   0.50    8.65    --  107.20  82.00-180.00   50
 23  ω     18.00 124.00   0.50    8.65    --  107.20 -82.00-120.00  212
 24  ω     60.00 137.00   0.50    8.65    --  107.20 -82.00  60.00  154
 25  ω     90.00 131.00   0.50    8.65    --  107.20  30.00 150.00   82
 26  ω     36.00 127.00   0.50    8.65    --  107.20 -82.00 -30.00  182
 27  ω     85.00 195.00   0.50    8.65    --  107.20  15.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0128590000
_diffrn_orient_matrix_UB_12      0.1181347000
_diffrn_orient_matrix_UB_13      -0.0872757000
_diffrn_orient_matrix_UB_21      0.0488834000
_diffrn_orient_matrix_UB_22      -0.0754650000
_diffrn_orient_matrix_UB_23      -0.0861383000
_diffrn_orient_matrix_UB_31      -0.1891032000
_diffrn_orient_matrix_UB_32      0.0097237000
_diffrn_orient_matrix_UB_33      -0.0108576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4215
_reflns_number_total             4788
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C103(H103), C104(H104), C105(H105), C106(H106), C109(H109),
  C111(H111), C112(H112), C113(H113), C114(H114), C116(H116)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.05323(12) 0.52853(8) 0.22821(7) 0.0304(2) Uani 1 1 d . . . . .
N1 N 0.24827(12) 0.34353(9) 0.60322(8) 0.0209(2) Uani 1 1 d . . . . .
N2 N 0.24200(11) 0.45503(9) 0.53580(7) 0.0185(2) Uani 1 1 d . . . . .
C1 C 0.20038(13) 0.27431(10) 0.54692(9) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.16135(13) 0.34119(10) 0.44415(9) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.11627(15) 0.27966(11) 0.37353(9) 0.0235(2) Uani 1 1 d . . . . .
H3 H 0.087881 0.322788 0.305116 0.028 Uiso 1 1 calc R U . . .
C4 C 0.11483(16) 0.15649(12) 0.40675(10) 0.0269(3) Uani 1 1 d . . . . .
H4 H 0.089115 0.113611 0.359311 0.032 Uiso 1 1 calc R U . . .
C5 C 0.15069(16) 0.09109(11) 0.51005(10) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.146462 0.005875 0.530447 0.032 Uiso 1 1 calc R U . . .
C6 C 0.19117(15) 0.14769(11) 0.58092(10) 0.0244(2) Uani 1 1 d . . . . .
H6 H 0.212397 0.103687 0.650567 0.029 Uiso 1 1 calc R U . . .
C7 C 0.18848(13) 0.46098(10) 0.43907(9) 0.0186(2) Uani 1 1 d . . . . .
C8 C 0.17690(14) 0.57701(11) 0.36399(9) 0.0208(2) Uani 1 1 d . . . . .
C9 C 0.22846(14) 0.67385(11) 0.38724(9) 0.0226(2) Uani 1 1 d . . . . .
H9 H 0.222619 0.749851 0.336659 0.027 Uiso 1 1 calc R U . . .
C10 C 0.29071(14) 0.66364(11) 0.48543(9) 0.0210(2) Uani 1 1 d . . . . .
C11 C 0.34781(15) 0.76159(11) 0.50984(10) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.346435 0.837689 0.459479 0.030 Uiso 1 1 calc R U . . .
C12 C 0.40544(15) 0.74781(12) 0.60593(11) 0.0268(3) Uani 1 1 d . . . . .
H12 H 0.445449 0.813821 0.621158 0.032 Uiso 1 1 calc R U . . .
C13 C 0.40515(15) 0.63617(12) 0.68156(10) 0.0264(3) Uani 1 1 d . . . . .
H13 H 0.444394 0.627695 0.747911 0.032 Uiso 1 1 calc R U . . .
C14 C 0.34881(15) 0.53862(11) 0.66106(10) 0.0236(2) Uani 1 1 d . . . . .
H14 H 0.347400 0.463775 0.712963 0.028 Uiso 1 1 calc R U . . .
C15 C 0.29370(13) 0.55218(10) 0.56214(9) 0.0195(2) Uani 1 1 d . . . . .
C16 C 0.10406(15) 0.60156(11) 0.26345(9) 0.0242(2) Uani 1 1 d . . . . .
H16 H 0.096220 0.683011 0.222092 0.029 Uiso 1 1 calc R U . . .
O101 O 0.58871(13) 1.02226(9) -0.27854(8) 0.0371(2) Uani 1 1 d . . . . .
N101 N 0.29064(12) 0.84030(9) 0.10179(8) 0.0202(2) Uani 1 1 d . . . . .
N102 N 0.26849(11) 0.94915(8) 0.03092(7) 0.0182(2) Uani 1 1 d . . . . .
C101 C 0.41378(14) 0.77272(10) 0.04796(9) 0.0196(2) Uani 1 1 d . . . . .
C102 C 0.47117(14) 0.83778(10) -0.05662(9) 0.0189(2) Uani 1 1 d . . . . .
C103 C 0.59811(14) 0.77811(11) -0.12362(9) 0.0224(2) Uani 1 1 d . . . . .
H103 H 0.636435 0.819310 -0.194234 0.027 Uiso 1 1 calc R U . . .
C104 C 0.66398(15) 0.65938(11) -0.08372(10) 0.0259(3) Uani 1 1 d . . . . .
H104 H 0.748346 0.617980 -0.127871 0.031 Uiso 1 1 calc R U . . .
C105 C 0.60934(16) 0.59669(11) 0.02191(11) 0.0268(3) Uani 1 1 d . . . . .
H105 H 0.660431 0.515205 0.047322 0.032 Uiso 1 1 calc R U . . .
C106 C 0.48522(15) 0.65051(11) 0.08794(10) 0.0244(3) Uani 1 1 d . . . . .
H106 H 0.448145 0.607535 0.158152 0.029 Uiso 1 1 calc R U . . .
C107 C 0.37438(13) 0.95495(10) -0.06546(9) 0.0183(2) Uani 1 1 d . . . . .
C108 C 0.36268(14) 1.06930(11) -0.14256(9) 0.0200(2) Uani 1 1 d . . . . .
C109 C 0.24331(14) 1.16478(11) -0.12099(9) 0.0207(2) Uani 1 1 d . . . . .
H109 H 0.234662 1.239588 -0.173046 0.025 Uiso 1 1 calc R U . . .
C110 C 0.13183(14) 1.15498(10) -0.02267(9) 0.0201(2) Uani 1 1 d . . . . .
C111 C 0.00933(15) 1.25293(11) 0.00155(10) 0.0243(3) Uani 1 1 d . . . . .
H111 H -0.003185 1.328148 -0.049760 0.029 Uiso 1 1 calc R U . . .
C112 C -0.09174(15) 1.23991(12) 0.09893(10) 0.0270(3) Uani 1 1 d . . . . .
H112 H -0.173999 1.306076 0.114467 0.032 Uiso 1 1 calc R U . . .
C113 C -0.07408(15) 1.12955(12) 0.17537(10) 0.0261(3) Uani 1 1 d . . . . .
H113 H -0.145108 1.121652 0.242230 0.031 Uiso 1 1 calc R U . . .
C114 C 0.04481(14) 1.03221(11) 0.15510(9) 0.0226(2) Uani 1 1 d . . . . .
H114 H 0.057001 0.957863 0.207517 0.027 Uiso 1 1 calc R U . . .
C115 C 0.14708(13) 1.04517(10) 0.05580(9) 0.0187(2) Uani 1 1 d . . . . .
C116 C 0.47903(15) 1.09447(11) -0.24341(9) 0.0245(3) Uani 1 1 d . . . . .
H116 H 0.466448 1.175780 -0.285008 0.029 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
O1 C16 1.2100(16) . ?
N1 N2 1.3542(13) . ?
N1 C1 1.3500(15) . ?
N2 C7 1.3866(14) . ?
N2 C15 1.3937(15) . ?
C1 C2 1.4242(15) . ?
C1 C6 1.4173(16) . ?
C2 C3 1.4199(16) . ?
C2 C7 1.4116(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3688(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.4187(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3663(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4375(16) . ?
C8 C9 1.3701(17) . ?
C8 C16 1.4738(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.4276(17) . ?
C10 C11 1.4114(16) . ?
C10 C15 1.4095(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3759(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.4051(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3803(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.4017(17) . ?
C16 H16 0.9500 . ?
O101 C116 1.2078(16) . ?
N101 N102 1.3557(13) . ?
N101 C101 1.3521(15) . ?
N102 C107 1.3856(14) . ?
N102 C115 1.3962(14) . ?
C101 C102 1.4234(16) . ?
C101 C106 1.4165(16) . ?
C102 C103 1.4185(16) . ?
C102 C107 1.4123(15) . ?
C103 H103 0.9500 . ?
C103 C104 1.3708(17) . ?
C104 H104 0.9500 . ?
C104 C105 1.4197(18) . ?
C105 H105 0.9500 . ?
C105 C106 1.3658(18) . ?
C106 H106 0.9500 . ?
C107 C108 1.4358(16) . ?
C108 C109 1.3705(16) . ?
C108 C116 1.4742(16) . ?
C109 H109 0.9500 . ?
C109 C110 1.4246(16) . ?
C110 C111 1.4140(16) . ?
C110 C115 1.4089(16) . ?
C111 H111 0.9500 . ?
C111 C112 1.3745(18) . ?
C112 H112 0.9500 . ?
C112 C113 1.4010(18) . ?
C113 H113 0.9500 . ?
C113 C114 1.3792(17) . ?
C114 H114 0.9500 . ?
C114 C115 1.3989(16) . ?
C116 H116 0.9500 . ?

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
C1 N1 N2 103.37(9) . . ?
N1 N2 C7 114.42(9) . . ?
N1 N2 C15 121.29(9) . . ?
C7 N2 C15 124.23(10) . . ?
N1 C1 C2 112.95(10) . . ?
N1 C1 C6 125.97(11) . . ?
C6 C1 C2 121.07(11) . . ?
C3 C2 C1 119.57(11) . . ?
C7 C2 C1 104.37(10) . . ?
C7 C2 C3 135.98(11) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.16(11) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.82(11) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.61(12) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.70(11) . . ?
C5 C6 H6 121.2 . . ?
N2 C7 C2 104.89(9) . . ?
N2 C7 C8 117.45(10) . . ?
C2 C7 C8 137.66(11) . . ?
C7 C8 C16 123.91(11) . . ?
C9 C8 C7 119.52(11) . . ?
C9 C8 C16 116.50(11) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.79(11) . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 122.61(11) . . ?
C15 C10 C9 119.14(11) . . ?
C15 C10 C11 118.25(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.58(11) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.04(11) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.09(12) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.68(11) . . ?
C15 C14 H14 120.7 . . ?
N2 C15 C10 117.71(10) . . ?
N2 C15 C14 120.95(10) . . ?
C14 C15 C10 121.33(11) . . ?
O1 C16 C8 126.64(11) . . ?
O1 C16 H16 116.7 . . ?
C8 C16 H16 116.7 . . ?
C101 N101 N102 103.25(9) . . ?
N101 N102 C107 114.45(9) . . ?
N101 N102 C115 121.22(9) . . ?
C107 N102 C115 124.34(9) . . ?
N101 C101 C102 113.01(10) . . ?
N101 C101 C106 125.76(11) . . ?
C106 C101 C102 121.22(11) . . ?
C103 C102 C101 119.55(11) . . ?
C107 C102 C101 104.33(10) . . ?
C107 C102 C103 136.11(11) . . ?
C102 C103 H103 120.9 . . ?
C104 C103 C102 118.20(11) . . ?
C104 C103 H103 120.9 . . ?
C103 C104 H104 119.2 . . ?
C103 C104 C105 121.68(11) . . ?
C105 C104 H104 119.2 . . ?
C104 C105 H105 119.1 . . ?
C106 C105 C104 121.71(11) . . ?
C106 C105 H105 119.1 . . ?
C101 C106 H106 121.2 . . ?
C105 C106 C101 117.60(11) . . ?
C105 C106 H106 121.2 . . ?
N102 C107 C102 104.95(9) . . ?
N102 C107 C108 117.38(10) . . ?
C102 C107 C108 137.65(11) . . ?
C107 C108 C116 123.98(11) . . ?
C109 C108 C107 119.57(10) . . ?
C109 C108 C116 116.36(10) . . ?
C108 C109 H109 119.1 . . ?
C108 C109 C110 121.84(11) . . ?
C110 C109 H109 119.1 . . ?
C111 C110 C109 122.64(11) . . ?
C115 C110 C109 119.24(11) . . ?
C115 C110 C111 118.07(11) . . ?
C110 C111 H111 119.8 . . ?
C112 C111 C110 120.36(11) . . ?
C112 C111 H111 119.8 . . ?
C111 C112 H112 119.8 . . ?
C111 C112 C113 120.34(11) . . ?
C113 C112 H112 119.8 . . ?
C112 C113 H113 119.5 . . ?
C114 C113 C112 121.04(11) . . ?
C114 C113 H113 119.5 . . ?
C113 C114 H114 120.7 . . ?
C113 C114 C115 118.65(11) . . ?
C115 C114 H114 120.7 . . ?
N102 C115 C110 117.53(10) . . ?
N102 C115 C114 120.95(10) . . ?
C114 C115 C110 121.53(11) . . ?
O101 C116 C108 126.64(11) . . ?
O101 C116 H116 116.7 . . ?
C108 C116 H116 116.7 . . ?

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
N1 N2 C7 C2 -1.34(12) . . . . ?
N1 N2 C7 C8 179.30(9) . . . . ?
N1 N2 C15 C10 177.07(9) . . . . ?
N1 N2 C15 C14 -2.11(16) . . . . ?
N1 C1 C2 C3 177.19(10) . . . . ?
N1 C1 C2 C7 -0.03(12) . . . . ?
N1 C1 C6 C5 -175.74(11) . . . . ?
N2 N1 C1 C2 -0.73(12) . . . . ?
N2 N1 C1 C6 177.86(10) . . . . ?
N2 C7 C8 C9 4.09(15) . . . . ?
N2 C7 C8 C16 -172.79(10) . . . . ?
C1 N1 N2 C7 1.29(12) . . . . ?
C1 N1 N2 C15 -175.86(9) . . . . ?
C1 C2 C3 C4 -1.09(16) . . . . ?
C1 C2 C7 N2 0.77(11) . . . . ?
C1 C2 C7 C8 179.93(12) . . . . ?
C2 C1 C6 C5 2.74(17) . . . . ?
C2 C3 C4 C5 2.36(18) . . . . ?
C2 C7 C8 C9 -175.00(12) . . . . ?
C2 C7 C8 C16 8.1(2) . . . . ?
C3 C2 C7 N2 -175.76(12) . . . . ?
C3 C2 C7 C8 3.4(2) . . . . ?
C3 C4 C5 C6 -1.07(19) . . . . ?
C4 C5 C6 C1 -1.51(18) . . . . ?
C6 C1 C2 C3 -1.47(16) . . . . ?
C6 C1 C2 C7 -178.70(10) . . . . ?
C7 N2 C15 C10 0.21(16) . . . . ?
C7 N2 C15 C14 -178.97(10) . . . . ?
C7 C2 C3 C4 175.04(12) . . . . ?
C7 C8 C9 C10 -1.26(16) . . . . ?
C7 C8 C16 O1 -3.93(19) . . . . ?
C8 C9 C10 C11 178.60(10) . . . . ?
C8 C9 C10 C15 -2.26(17) . . . . ?
C9 C8 C16 O1 179.11(11) . . . . ?
C9 C10 C11 C12 179.45(10) . . . . ?
C9 C10 C15 N2 2.77(15) . . . . ?
C9 C10 C15 C14 -178.06(10) . . . . ?
C10 C11 C12 C13 -1.08(18) . . . . ?
C11 C10 C15 N2 -178.05(9) . . . . ?
C11 C10 C15 C14 1.13(16) . . . . ?
C11 C12 C13 C14 0.46(18) . . . . ?
C12 C13 C14 C15 0.93(18) . . . . ?
C13 C14 C15 N2 177.42(10) . . . . ?
C13 C14 C15 C10 -1.73(17) . . . . ?
C15 N2 C7 C2 175.72(9) . . . . ?
C15 N2 C7 C8 -3.65(15) . . . . ?
C15 C10 C11 C12 0.30(16) . . . . ?
C16 C8 C9 C10 175.85(10) . . . . ?
N101 N102 C107 C102 1.42(12) . . . . ?
N101 N102 C107 C108 -177.44(9) . . . . ?
N101 N102 C115 C110 -179.69(9) . . . . ?
N101 N102 C115 C114 0.33(15) . . . . ?
N101 C101 C102 C103 -178.83(9) . . . . ?
N101 C101 C102 C107 0.51(12) . . . . ?
N101 C101 C106 C105 -179.83(11) . . . . ?
N102 N101 C101 C102 0.31(12) . . . . ?
N102 N101 C101 C106 179.22(11) . . . . ?
N102 C107 C108 C109 -3.48(15) . . . . ?
N102 C107 C108 C116 172.85(10) . . . . ?
C101 N101 N102 C107 -1.08(12) . . . . ?
C101 N101 N102 C115 178.65(9) . . . . ?
C101 C102 C103 C104 -1.37(16) . . . . ?
C101 C102 C107 N102 -1.08(11) . . . . ?
C101 C102 C107 C108 177.40(12) . . . . ?
C102 C101 C106 C105 -1.00(17) . . . . ?
C102 C103 C104 C105 -0.56(18) . . . . ?
C102 C107 C108 C109 178.17(12) . . . . ?
C102 C107 C108 C116 -5.5(2) . . . . ?
C103 C102 C107 N102 178.09(12) . . . . ?
C103 C102 C107 C108 -3.4(2) . . . . ?
C103 C104 C105 C106 1.81(19) . . . . ?
C104 C105 C106 C101 -0.97(18) . . . . ?
C106 C101 C102 C103 2.20(16) . . . . ?
C106 C101 C102 C107 -178.46(10) . . . . ?
C107 N102 C115 C110 0.02(15) . . . . ?
C107 N102 C115 C114 -179.97(10) . . . . ?
C107 C102 C103 C104 179.55(12) . . . . ?
C107 C108 C109 C110 1.38(16) . . . . ?
C107 C108 C116 O101 6.1(2) . . . . ?
C108 C109 C110 C111 179.20(10) . . . . ?
C108 C109 C110 C115 1.56(16) . . . . ?
C109 C108 C116 O101 -177.47(12) . . . . ?
C109 C110 C111 C112 -178.02(11) . . . . ?
C109 C110 C115 N102 -2.24(15) . . . . ?
C109 C110 C115 C114 177.74(10) . . . . ?
C110 C111 C112 C113 0.21(18) . . . . ?
C111 C110 C115 N102 180.00(9) . . . . ?
C111 C110 C115 C114 -0.01(16) . . . . ?
C111 C112 C113 C114 0.29(19) . . . . ?
C112 C113 C114 C115 -0.64(18) . . . . ?
C113 C114 C115 N102 -179.52(10) . . . . ?
C113 C114 C115 C110 0.50(17) . . . . ?
C115 N102 C107 C102 -178.30(9) . . . . ?
C115 N102 C107 C108 2.84(15) . . . . ?
C115 C110 C111 C112 -0.35(17) . . . . ?
C116 C108 C109 C110 -175.22(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.855
_oxdiff_exptl_absorpt_empirical_full_min 0.663
