# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_sc_3_52a_2_a
_database_code_depnum_ccdc_archive 'CCDC 2308710'
loop_
_audit_author_name
_audit_author_address
'Chinmay Chowdhury'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        SC_3_52A_2_a
_chemical_formula_moiety         'C18 H13 N3 O2'
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31
_chemical_melting_point          ?
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                   6.9020(6)
_cell_length_b                   13.8797(12)
_cell_length_c                   16.3061(14)
_cell_angle_alpha                66.241(4)
_cell_angle_beta                 89.878(3)
_cell_angle_gamma                76.826(3)
_cell_volume                     1385.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8124
_cell_measurement_temperature    106.00
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.7404.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12890
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.820
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_temperature      106.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4431
_reflns_number_total             4911
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0959
_refine_ls_restrained_S_all      1.141
_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)+(0.0498P)²+12.6914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2987
_refine_ls_wR_factor_ref         0.3005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27),
  C30(H30), C31(H31), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C35(H35A,H35B,H35C)
;
_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
C1 C 0.2419(7) 0.5889(4) 0.1781(3) 0.0159(10) Uani 1 1 d . . . . .
H1 H 0.230245 0.664978 0.149779 0.019 Uiso 1 1 calc R U . . .
N1 N 0.2769(6) 0.3880(3) 0.4050(3) 0.0144(9) Uani 1 1 d . . . . .
O1 O 0.2008(6) 0.6229(3) 0.8853(3) 0.0252(9) Uani 1 1 d . . . . .
C2 C 0.2496(7) 0.5285(4) 0.1269(3) 0.0161(11) Uani 1 1 d . . . . .
H2 H 0.242843 0.563520 0.063150 0.019 Uiso 1 1 calc R U . . .
N2 N 0.2567(6) 0.4715(3) 0.5077(3) 0.0144(9) Uani 1 1 d . . . . .
O2 O 0.2528(6) 0.4472(3) 0.9373(3) 0.0259(9) Uani 1 1 d . . . . .
C3 C 0.2675(7) 0.4163(4) 0.1692(3) 0.0171(11) Uani 1 1 d . . . . .
H3 H 0.271792 0.376655 0.133113 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2789(7) 0.3615(4) 0.2618(3) 0.0151(10) Uani 1 1 d . . . . .
H4 H 0.292588 0.285290 0.289961 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2695(7) 0.4233(4) 0.3123(3) 0.0134(10) Uani 1 1 d . . . . .
C6 C 0.2514(7) 0.5358(4) 0.2713(3) 0.0137(10) Uani 1 1 d . . . . .
N6 N 0.2290(6) 0.5371(4) 0.8750(3) 0.0167(9) Uani 1 1 d . . . . .
C7 C 0.2433(7) 0.5708(4) 0.3434(3) 0.0142(10) Uani 1 1 d . . . . .
C8 C 0.2585(7) 0.4777(4) 0.4250(3) 0.0131(10) Uani 1 1 d . . . . .
C9 C 0.2374(7) 0.5677(4) 0.5141(4) 0.0160(11) Uani 1 1 d . . . . .
C10 C 0.2229(8) 0.6651(4) 0.4394(4) 0.0187(11) Uani 1 1 d . . . . .
H10 H 0.211438 0.730298 0.447344 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2250(8) 0.6679(4) 0.3529(3) 0.0166(11) Uani 1 1 d . . . . .
H11 H 0.214210 0.734355 0.301703 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2355(7) 0.5610(4) 0.6074(3) 0.0145(10) Uani 1 1 d . . . . .
C13 C 0.2182(7) 0.6538(4) 0.6253(4) 0.0167(11) Uani 1 1 d . . . . .
H13 H 0.207394 0.722721 0.576877 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2168(8) 0.6451(4) 0.7129(4) 0.0164(11) Uani 1 1 d . . . . .
H14 H 0.205044 0.707696 0.724772 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2327(7) 0.5451(4) 0.7827(3) 0.0152(10) Uani 1 1 d . . . . .
C16 C 0.2502(7) 0.4512(4) 0.7680(4) 0.0164(11) Uani 1 1 d . . . . .
H16 H 0.261434 0.382568 0.816828 0.020 Uiso 1 1 calc R U . . .
C17 C 0.2508(7) 0.4610(4) 0.6803(4) 0.0179(11) Uani 1 1 d . . . . .
H17 H 0.262026 0.397969 0.669156 0.021 Uiso 1 1 calc R U . . .
C36 C 0.2990(8) 0.2771(4) 0.4702(3) 0.0198(11) Uani 1 1 d . . . . .
H36A H 0.330728 0.271887 0.530634 0.030 Uiso 1 1 calc R U . . .
H36B H 0.407459 0.228764 0.455967 0.030 Uiso 1 1 calc R U . . .
H36C H 0.173901 0.255754 0.468090 0.030 Uiso 1 1 calc R U . . .
N3 N 0.6625(6) 0.1139(3) 1.0933(3) 0.0133(9) Uani 1 1 d . . . . .
O3 O 0.8387(7) -0.1050(3) 0.6050(3) 0.0276(10) Uani 1 1 d . . . . .
N4 N 0.7239(6) 0.0328(3) 0.9887(3) 0.0144(9) Uani 1 1 d . . . . .
O4 O 0.7305(6) 0.0697(3) 0.5565(3) 0.0259(9) Uani 1 1 d . . . . .
N5 N 0.7844(6) -0.0221(4) 0.6183(3) 0.0184(10) Uani 1 1 d . . . . .
C18 C 0.6406(7) 0.1383(4) 1.2372(3) 0.0144(10) Uani 1 1 d . . . . .
H18 H 0.584837 0.214574 1.209512 0.017 Uiso 1 1 calc R U . . .
C19 C 0.6796(8) 0.0828(4) 1.3306(3) 0.0165(11) Uani 1 1 d . . . . .
H19 H 0.649378 0.121850 1.367267 0.020 Uiso 1 1 calc R U . . .
C20 C 0.7626(8) -0.0293(4) 1.3712(3) 0.0174(11) Uani 1 1 d . . . . .
H20 H 0.789505 -0.065165 1.434836 0.021 Uiso 1 1 calc R U . . .
C21 C 0.8064(7) -0.0892(4) 1.3198(3) 0.0165(11) Uani 1 1 d . . . . .
H21 H 0.861670 -0.165462 1.348024 0.020 Uiso 1 1 calc R U . . .
C22 C 0.7684(7) -0.0362(4) 1.2268(3) 0.0146(10) Uani 1 1 d . . . . .
C23 C 0.6858(7) 0.0783(4) 1.1865(3) 0.0118(10) Uani 1 1 d . . . . .
C24 C 0.7917(7) -0.0695(4) 1.1531(3) 0.0140(10) Uani 1 1 d . . . . .
C25 C 0.7265(7) 0.0260(4) 1.0731(3) 0.0144(10) Uani 1 1 d . . . . .
C26 C 0.8556(8) -0.1663(4) 1.1432(4) 0.0180(11) Uani 1 1 d . . . . .
H26 H 0.900000 -0.233609 1.194184 0.022 Uiso 1 1 calc R U . . .
C27 C 0.8527(8) -0.1618(4) 1.0568(3) 0.0170(11) Uani 1 1 d . . . . .
H27 H 0.894005 -0.226907 1.048192 0.020 Uiso 1 1 calc R U . . .
C28 C 0.7895(7) -0.0623(4) 0.9820(3) 0.0144(10) Uani 1 1 d . . . . .
C29 C 0.7881(7) -0.0546(4) 0.8874(3) 0.0141(10) Uani 1 1 d . . . . .
C30 C 0.7035(7) 0.0457(4) 0.8166(3) 0.0162(11) Uani 1 1 d . . . . .
H30 H 0.647505 0.106869 0.829108 0.019 Uiso 1 1 calc R U . . .
C31 C 0.7003(8) 0.0568(4) 0.7283(4) 0.0179(11) Uani 1 1 d . . . . .
H31 H 0.641765 0.124869 0.680132 0.022 Uiso 1 1 calc R U . . .
C32 C 0.7846(7) -0.0338(4) 0.7115(3) 0.0162(11) Uani 1 1 d . . . . .
C33 C 0.8668(7) -0.1332(4) 0.7799(4) 0.0172(11) Uani 1 1 d . . . . .
H33 H 0.920870 -0.194358 0.767057 0.021 Uiso 1 1 calc R U . . .
C34 C 0.8703(7) -0.1437(4) 0.8685(3) 0.0161(10) Uani 1 1 d . . . . .
H34 H 0.929200 -0.212079 0.916225 0.019 Uiso 1 1 calc R U . . .
C35 C 0.5781(8) 0.2252(4) 1.0300(3) 0.0199(11) Uani 1 1 d . . . . .
H35A H 0.439793 0.248884 1.041508 0.030 Uiso 1 1 calc R U . . .
H35B H 0.580303 0.229875 0.968449 0.030 Uiso 1 1 calc R U . . .
H35C H 0.657132 0.272110 1.037328 0.030 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
C1 H1 0.9500 . ?
C1 C2 1.395(7) . ?
C1 C6 1.391(7) . ?
N1 C5 1.384(6) . ?
N1 C8 1.388(6) . ?
N1 C36 1.449(7) . ?
O1 N6 1.240(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(8) . ?
N2 C8 1.316(7) . ?
N2 C9 1.357(7) . ?
O2 N6 1.226(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(7) . ?
C5 C6 1.404(7) . ?
C6 C7 1.438(7) . ?
N6 C15 1.465(6) . ?
C7 C8 1.417(7) . ?
C7 C11 1.395(7) . ?
C9 C10 1.390(8) . ?
C9 C12 1.487(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(7) . ?
C12 C17 1.397(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(7) . ?
C15 C16 1.397(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(7) . ?
C17 H17 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N3 C23 1.393(6) . ?
N3 C25 1.368(7) . ?
N3 C35 1.449(6) . ?
O3 N5 1.232(6) . ?
N4 C25 1.339(7) . ?
N4 C28 1.342(7) . ?
O4 N5 1.236(6) . ?
N5 C32 1.462(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(7) . ?
C18 C23 1.382(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.398(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(7) . ?
C22 C23 1.424(7) . ?
C22 C24 1.449(7) . ?
C24 C25 1.414(7) . ?
C24 C26 1.389(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.398(7) . ?
C28 C29 1.502(7) . ?
C29 C30 1.396(7) . ?
C29 C34 1.391(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.391(7) . ?
C32 C33 1.370(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(7) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

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 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.7(5) . . ?
C5 N1 C8 108.2(4) . . ?
C5 N1 C36 126.3(4) . . ?
C8 N1 C36 125.5(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C8 N2 C9 114.7(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(5) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.1(5) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 128.2(5) . . ?
N1 C5 C6 110.1(4) . . ?
C4 C5 C6 121.8(5) . . ?
C1 C6 C5 120.1(5) . . ?
C1 C6 C7 134.0(5) . . ?
C5 C6 C7 105.9(4) . . ?
O1 N6 C15 117.4(4) . . ?
O2 N6 O1 123.8(4) . . ?
O2 N6 C15 118.8(4) . . ?
C8 C7 C6 107.3(4) . . ?
C11 C7 C6 137.6(5) . . ?
C11 C7 C8 115.1(4) . . ?
N1 C8 C7 108.4(4) . . ?
N2 C8 N1 123.2(5) . . ?
N2 C8 C7 128.4(5) . . ?
N2 C9 C10 122.8(5) . . ?
N2 C9 C12 114.9(4) . . ?
C10 C9 C12 122.3(5) . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C7 C11 C10 118.5(5) . . ?
C7 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C9 121.7(5) . . ?
C17 C12 C9 120.2(5) . . ?
C17 C12 C13 118.2(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(5) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 N6 119.0(5) . . ?
C14 C15 C16 121.9(5) . . ?
C16 C15 N6 119.1(5) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.0(5) . . ?
C17 C16 H16 121.0 . . ?
C12 C17 H17 119.0 . . ?
C16 C17 C12 122.0(5) . . ?
C16 C17 H17 119.0 . . ?
N1 C36 H36A 109.5 . . ?
N1 C36 H36B 109.5 . . ?
N1 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C23 N3 C35 124.8(4) . . ?
C25 N3 C23 108.4(4) . . ?
C25 N3 C35 126.7(4) . . ?
C25 N4 C28 115.0(4) . . ?
O3 N5 O4 122.9(4) . . ?
O3 N5 C32 118.1(4) . . ?
O4 N5 C32 119.1(4) . . ?
C19 C18 H18 121.2 . . ?
C23 C18 H18 121.2 . . ?
C23 C18 C19 117.6(5) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(5) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 119.1(5) . . ?
C21 C22 C24 135.0(5) . . ?
C23 C22 C24 105.9(4) . . ?
N3 C23 C22 109.2(4) . . ?
C18 C23 N3 128.8(5) . . ?
C18 C23 C22 122.0(5) . . ?
C25 C24 C22 106.5(4) . . ?
C26 C24 C22 136.9(5) . . ?
C26 C24 C25 116.6(5) . . ?
N3 C25 C24 110.0(4) . . ?
N4 C25 N3 123.3(5) . . ?
N4 C25 C24 126.6(5) . . ?
C24 C26 H26 121.0 . . ?
C27 C26 C24 118.0(5) . . ?
C27 C26 H26 121.0 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.7(5) . . ?
C28 C27 H27 119.7 . . ?
N4 C28 C27 123.1(5) . . ?
N4 C28 C29 115.0(4) . . ?
C27 C28 C29 121.9(5) . . ?
C30 C29 C28 118.6(5) . . ?
C34 C29 C28 122.1(5) . . ?
C34 C29 C30 119.3(5) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.7(5) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.6 . . ?
C30 C31 C32 118.7(5) . . ?
C32 C31 H31 120.6 . . ?
C31 C32 N5 118.9(5) . . ?
C33 C32 N5 119.4(5) . . ?
C33 C32 C31 121.7(5) . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.3(5) . . ?
C34 C33 H33 120.3 . . ?
C29 C34 C33 120.3(5) . . ?
C29 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
C1 C2 C3 C4 -0.3(8) . . . . ?
C1 C6 C7 C8 179.2(5) . . . . ?
C1 C6 C7 C11 -0.6(10) . . . . ?
N1 C5 C6 C1 179.8(4) . . . . ?
N1 C5 C6 C7 -1.2(5) . . . . ?
O1 N6 C15 C14 3.8(7) . . . . ?
O1 N6 C15 C16 -175.6(4) . . . . ?
C2 C1 C6 C5 0.3(7) . . . . ?
C2 C1 C6 C7 -178.3(5) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
N2 C9 C10 C11 0.9(8) . . . . ?
N2 C9 C12 C13 179.4(4) . . . . ?
N2 C9 C12 C17 -0.6(7) . . . . ?
O2 N6 C15 C14 -176.5(5) . . . . ?
O2 N6 C15 C16 4.1(7) . . . . ?
C3 C4 C5 N1 179.7(5) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 C7 179.2(4) . . . . ?
C5 N1 C8 N2 178.9(4) . . . . ?
C5 N1 C8 C7 -1.2(5) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C5 C6 C7 C11 -179.4(6) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
C6 C7 C8 N1 0.5(5) . . . . ?
C6 C7 C8 N2 -179.6(5) . . . . ?
C6 C7 C11 C10 179.7(5) . . . . ?
N6 C15 C16 C17 179.2(4) . . . . ?
C8 N1 C5 C4 -178.9(5) . . . . ?
C8 N1 C5 C6 1.5(5) . . . . ?
C8 N2 C9 C10 -0.7(7) . . . . ?
C8 N2 C9 C12 -180.0(4) . . . . ?
C8 C7 C11 C10 -0.1(7) . . . . ?
C9 N2 C8 N1 -180.0(4) . . . . ?
C9 N2 C8 C7 0.1(7) . . . . ?
C9 C10 C11 C7 -0.4(8) . . . . ?
C9 C12 C13 C14 180.0(5) . . . . ?
C9 C12 C17 C16 179.8(5) . . . . ?
C10 C9 C12 C13 0.2(7) . . . . ?
C10 C9 C12 C17 -179.9(5) . . . . ?
C11 C7 C8 N1 -179.7(4) . . . . ?
C11 C7 C8 N2 0.3(8) . . . . ?
C12 C9 C10 C11 -179.9(5) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C12 C17 C16 -0.3(7) . . . . ?
C13 C14 C15 N6 -179.4(4) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C14 C15 C16 C17 -0.2(8) . . . . ?
C15 C16 C17 C12 0.3(7) . . . . ?
C17 C12 C13 C14 0.1(7) . . . . ?
C36 N1 C5 C4 0.9(8) . . . . ?
C36 N1 C5 C6 -178.7(5) . . . . ?
C36 N1 C8 N2 -0.9(7) . . . . ?
C36 N1 C8 C7 179.0(4) . . . . ?
O3 N5 C32 C31 -171.9(5) . . . . ?
O3 N5 C32 C33 7.9(7) . . . . ?
N4 C28 C29 C30 -6.0(6) . . . . ?
N4 C28 C29 C34 173.3(4) . . . . ?
O4 N5 C32 C31 8.1(7) . . . . ?
O4 N5 C32 C33 -172.1(5) . . . . ?
N5 C32 C33 C34 178.7(4) . . . . ?
C18 C19 C20 C21 -0.8(8) . . . . ?
C19 C18 C23 N3 -179.6(5) . . . . ?
C19 C18 C23 C22 0.3(7) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C20 C21 C22 C24 -179.5(5) . . . . ?
C21 C22 C23 N3 179.4(4) . . . . ?
C21 C22 C23 C18 -0.6(7) . . . . ?
C21 C22 C24 C25 -179.2(5) . . . . ?
C21 C22 C24 C26 1.9(10) . . . . ?
C22 C24 C25 N3 -1.1(5) . . . . ?
C22 C24 C25 N4 179.4(4) . . . . ?
C22 C24 C26 C27 179.5(5) . . . . ?
C23 N3 C25 N4 -180.0(4) . . . . ?
C23 N3 C25 C24 0.5(5) . . . . ?
C23 C18 C19 C20 0.3(7) . . . . ?
C23 C22 C24 C25 1.2(5) . . . . ?
C23 C22 C24 C26 -177.7(6) . . . . ?
C24 C22 C23 N3 -0.9(5) . . . . ?
C24 C22 C23 C18 179.1(4) . . . . ?
C24 C26 C27 C28 0.8(8) . . . . ?
C25 N3 C23 C18 -179.8(5) . . . . ?
C25 N3 C23 C22 0.3(5) . . . . ?
C25 N4 C28 C27 1.2(7) . . . . ?
C25 N4 C28 C29 -179.5(4) . . . . ?
C25 C24 C26 C27 0.7(7) . . . . ?
C26 C24 C25 N3 178.1(4) . . . . ?
C26 C24 C25 N4 -1.4(7) . . . . ?
C26 C27 C28 N4 -1.9(8) . . . . ?
C26 C27 C28 C29 178.9(5) . . . . ?
C27 C28 C29 C30 173.3(5) . . . . ?
C27 C28 C29 C34 -7.5(7) . . . . ?
C28 N4 C25 N3 -179.0(4) . . . . ?
C28 N4 C25 C24 0.5(7) . . . . ?
C28 C29 C30 C31 179.5(4) . . . . ?
C28 C29 C34 C33 -179.7(4) . . . . ?
C29 C30 C31 C32 -0.5(7) . . . . ?
C30 C29 C34 C33 -0.5(7) . . . . ?
C30 C31 C32 N5 -179.0(4) . . . . ?
C30 C31 C32 C33 1.1(7) . . . . ?
C31 C32 C33 C34 -1.4(8) . . . . ?
C32 C33 C34 C29 1.1(7) . . . . ?
C34 C29 C30 C31 0.2(7) . . . . ?
C35 N3 C23 C18 -1.6(8) . . . . ?
C35 N3 C23 C22 178.4(4) . . . . ?
C35 N3 C25 N4 2.0(8) . . . . ?
C35 N3 C25 C24 -177.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sc_a
_database_code_depnum_ccdc_archive 'CCDC 2308711'
loop_
_audit_author_name
_audit_author_address
'CHINMAY CHOWDHURY'
;INDIAN INSTITUTE OF CHEMICAL BIOLOGY
India
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        SC_3_73A
_chemical_formula_moiety         'C19 H16 N2'
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.4739(4)
_cell_length_b                   7.1393(2)
_cell_length_c                   14.6043(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.5760(10)
_cell_angle_gamma                90
_cell_volume                     1376.27(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    106.00
_cell_measurement_theta_max      66.851
_cell_measurement_theta_min      6.71
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4317
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1366 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.5735.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20579
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.861
_diffrn_reflns_theta_max         66.861
_diffrn_reflns_theta_min         6.708
_diffrn_ambient_temperature      106.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2292
_reflns_number_total             2336
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.060
_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)+(0.0574P)²+0.4790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1097
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
C1 C 0.40673(9) 0.26740(15) 0.42389(8) 0.0166(3) Uani 1 1 d . . . . .
N1 N 0.32241(7) 0.29958(13) 0.45900(7) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.50475(9) 0.25236(15) 0.48065(8) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.26030(8) 0.35173(14) 0.59965(7) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.51548(9) 0.27236(16) 0.57710(8) 0.0174(3) Uani 1 1 d . . . . .
H3 H 0.580550 0.264304 0.616666 0.021 Uiso 1 1 calc R U . . .
C4 C 0.43021(9) 0.30417(15) 0.61486(8) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.33654(9) 0.31611(15) 0.55107(8) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.30334(9) 0.36389(16) 0.69393(8) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.40936(9) 0.33492(16) 0.70694(8) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.46909(9) 0.34152(17) 0.79653(8) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.540224 0.322605 0.806150 0.025 Uiso 1 1 calc R U . . .
C9 C 0.42272(10) 0.37625(17) 0.87143(9) 0.0231(3) Uani 1 1 d . . . . .
H9 H 0.462423 0.380598 0.932996 0.028 Uiso 1 1 calc R U . . .
C10 C 0.31761(10) 0.40507(17) 0.85718(9) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.287639 0.429193 0.909581 0.028 Uiso 1 1 calc R U . . .
C11 C 0.25654(9) 0.39931(17) 0.76898(8) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.185486 0.418743 0.759934 0.026 Uiso 1 1 calc R U . . .
C12 C 0.15352(9) 0.37225(18) 0.55889(9) 0.0230(3) Uani 1 1 d . . . . .
H12A H 0.131585 0.499684 0.569959 0.035 Uiso 1 1 calc R U . . .
H12B H 0.114311 0.281980 0.587684 0.035 Uiso 1 1 calc R U . . .
H12C H 0.142486 0.348948 0.491473 0.035 Uiso 1 1 calc R U . . .
C13 C 0.59996(9) 0.22367(17) 0.44249(8) 0.0190(3) Uani 1 1 d . . . . .
H13A H 0.610911 0.089375 0.434779 0.028 Uiso 1 1 calc R U . . .
H13B H 0.657990 0.276633 0.486126 0.028 Uiso 1 1 calc R U . . .
H13C H 0.592709 0.286419 0.381826 0.028 Uiso 1 1 calc R U . . .
C14 C 0.38799(8) 0.25988(16) 0.31984(8) 0.0172(3) Uani 1 1 d . . . . .
C15 C 0.43735(9) 0.13298(16) 0.27136(8) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.483870 0.045610 0.305255 0.023 Uiso 1 1 calc R U . . .
C16 C 0.41938(9) 0.13282(17) 0.17445(9) 0.0206(3) Uani 1 1 d . . . . .
H16 H 0.453530 0.045531 0.142583 0.025 Uiso 1 1 calc R U . . .
C17 C 0.35172(9) 0.25963(18) 0.12383(8) 0.0220(3) Uani 1 1 d . . . . .
H17 H 0.340459 0.261093 0.057502 0.026 Uiso 1 1 calc R U . . .
C18 C 0.30054(9) 0.38454(17) 0.17093(9) 0.0218(3) Uani 1 1 d . . . . .
H18 H 0.253643 0.470757 0.136581 0.026 Uiso 1 1 calc R U . . .
C19 C 0.31761(9) 0.38384(17) 0.26763(8) 0.0193(3) Uani 1 1 d . . . . .
H19 H 0.281298 0.468183 0.299046 0.023 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
C1 N1 1.3566(15) . ?
C1 C2 1.4155(17) . ?
C1 C14 1.4905(16) . ?
N1 C5 1.3249(15) . ?
C2 C3 1.3942(16) . ?
C2 C13 1.5117(15) . ?
N2 C5 1.3841(15) . ?
N2 C6 1.3853(15) . ?
N2 C12 1.4499(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3892(16) . ?
C4 C5 1.4130(17) . ?
C4 C7 1.4447(16) . ?
C6 C7 1.4180(17) . ?
C6 C11 1.3929(17) . ?
C7 C8 1.3926(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3866(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.4046(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3829(18) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3977(17) . ?
C14 C19 1.4049(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3872(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3881(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3908(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3846(17) . ?
C19 H19 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
N1 C1 C2 123.04(11) . . ?
N1 C1 C14 114.08(10) . . ?
C2 C1 C14 122.80(10) . . ?
C5 N1 C1 115.98(10) . . ?
C1 C2 C13 123.74(10) . . ?
C3 C2 C1 118.64(10) . . ?
C3 C2 C13 117.56(10) . . ?
C5 N2 C6 108.38(10) . . ?
C5 N2 C12 125.84(10) . . ?
C6 N2 C12 125.78(10) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.44(11) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 116.65(11) . . ?
C3 C4 C7 136.48(11) . . ?
C5 C4 C7 106.84(10) . . ?
N1 C5 N2 124.50(11) . . ?
N1 C5 C4 126.24(11) . . ?
N2 C5 C4 109.25(10) . . ?
N2 C6 C7 109.49(10) . . ?
N2 C6 C11 128.91(11) . . ?
C11 C6 C7 121.60(11) . . ?
C6 C7 C4 106.04(10) . . ?
C8 C7 C4 134.11(11) . . ?
C8 C7 C6 119.85(11) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.70(12) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.65(12) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.83(11) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 H11 121.3 . . ?
C10 C11 C6 117.36(12) . . ?
C10 C11 H11 121.3 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C1 122.63(10) . . ?
C15 C14 C19 118.12(11) . . ?
C19 C14 C1 119.24(10) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.94(11) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.28(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.52(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.32(11) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.78(11) . . ?
C18 C19 H19 119.6 . . ?

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
C1 N1 C5 N2 179.03(10) . . . . ?
C1 N1 C5 C4 0.28(17) . . . . ?
C1 C2 C3 C4 0.73(16) . . . . ?
C1 C14 C15 C16 -178.69(10) . . . . ?
C1 C14 C19 C18 178.06(10) . . . . ?
N1 C1 C2 C3 -0.32(17) . . . . ?
N1 C1 C2 C13 -177.65(10) . . . . ?
N1 C1 C14 C15 -141.42(11) . . . . ?
N1 C1 C14 C19 38.19(14) . . . . ?
C2 C1 N1 C5 -0.18(16) . . . . ?
C2 C1 C14 C15 41.82(16) . . . . ?
C2 C1 C14 C19 -138.57(11) . . . . ?
C2 C3 C4 C5 -0.63(16) . . . . ?
C2 C3 C4 C7 -178.65(12) . . . . ?
N2 C6 C7 C4 0.11(13) . . . . ?
N2 C6 C7 C8 179.73(10) . . . . ?
N2 C6 C11 C10 -179.68(11) . . . . ?
C3 C4 C5 N1 0.12(17) . . . . ?
C3 C4 C5 N2 -178.78(10) . . . . ?
C3 C4 C7 C6 178.21(13) . . . . ?
C3 C4 C7 C8 -1.3(2) . . . . ?
C4 C7 C8 C9 179.62(12) . . . . ?
C5 N2 C6 C7 -0.24(13) . . . . ?
C5 N2 C6 C11 179.42(12) . . . . ?
C5 C4 C7 C6 0.06(12) . . . . ?
C5 C4 C7 C8 -179.48(13) . . . . ?
C6 N2 C5 N1 -178.65(10) . . . . ?
C6 N2 C5 C4 0.28(12) . . . . ?
C6 C7 C8 C9 0.13(17) . . . . ?
C7 C4 C5 N1 178.70(10) . . . . ?
C7 C4 C5 N2 -0.21(12) . . . . ?
C7 C6 C11 C10 -0.05(17) . . . . ?
C7 C8 C9 C10 -0.29(18) . . . . ?
C8 C9 C10 C11 0.29(19) . . . . ?
C9 C10 C11 C6 -0.11(18) . . . . ?
C11 C6 C7 C4 -179.58(11) . . . . ?
C11 C6 C7 C8 0.04(17) . . . . ?
C12 N2 C5 N1 1.53(18) . . . . ?
C12 N2 C5 C4 -179.55(11) . . . . ?
C12 N2 C6 C7 179.58(11) . . . . ?
C12 N2 C6 C11 -0.76(19) . . . . ?
C13 C2 C3 C4 178.23(10) . . . . ?
C14 C1 N1 C5 -176.93(9) . . . . ?
C14 C1 C2 C3 176.15(10) . . . . ?
C14 C1 C2 C13 -1.19(17) . . . . ?
C14 C15 C16 C17 0.06(17) . . . . ?
C15 C14 C19 C18 -2.31(16) . . . . ?
C15 C16 C17 C18 -1.25(18) . . . . ?
C16 C17 C18 C19 0.64(18) . . . . ?
C17 C18 C19 C14 1.17(17) . . . . ?
C19 C14 C15 C16 1.70(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
