# 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. 
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data_AZN-9
_database_code_depnum_ccdc_archive 'CCDC 2457150'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Azonitrile
_chemical_name_systematic        
(E)-4-((4-nonyloxyphenyl)diazenyl)benzonitrile
_chemical_formula_moiety         'C22 H27 N3 O'
_chemical_formula_sum            'C22 H27 N3 O'
_chemical_formula_weight         349.46
_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 0.0033 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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   5.8210(12)
_cell_length_b                   11.178(2)
_cell_length_c                   16.211(3)
_cell_angle_alpha                72.80(3)
_cell_angle_beta                 79.81(3)
_cell_angle_gamma                75.36(3)
_cell_volume                     969.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.9
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      1.20
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14482
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         27.794
_diffrn_reflns_theta_min         1.923
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3907
_reflns_number_total             4702
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0801P)²+0.2590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1495
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 O1(N3,N2,N1,C9,C13,C11,C7,C12,C10,C6,C2,C5,C3,C4,C16,C1,C8,C15,C18,C19,C20,
 C17,C14,C21,C22)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C17(H17A,H17B), C14(H14A,H14B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C7(H7), C12(H12), C10(H10), C6(H6), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.80200(5) 0.45312(3) 0.62228(2) 0.0252(2) Uani 1 1 d G . . . .
N3 N 0.06783(5) 0.83568(2) 0.47323(2) 0.0228(2) Uani 1 1 d G . . . .
N2 N 0.12653(5) 0.90614(3) 0.39956(2) 0.0237(2) Uani 1 1 d G . . . .
N1 N -0.74515(7) 1.38578(4) 0.21169(3) 0.0355(3) Uani 1 1 d G . . . .
C9 C 0.49527(5) 0.71922(3) 0.46762(2) 0.0228(2) Uani 1 1 d G . . . .
H9 H 0.533726 0.773139 0.411969 0.027 Uiso 1 1 calc R U . . .
C13 C 0.20469(5) 0.65620(3) 0.58926(2) 0.0230(2) Uani 1 1 d G . . . .
H13 H 0.044857 0.666862 0.616296 0.028 Uiso 1 1 calc R U . . .
C11 C 0.61487(5) 0.54245(2) 0.58966(2) 0.0220(2) Uani 1 1 d G . . . .
C7 C -0.47654(6) 1.11565(4) 0.36265(3) 0.0239(2) Uani 1 1 d G . . . .
H7 H -0.637520 1.124968 0.388546 0.029 Uiso 1 1 calc R U . . .
C12 C 0.37997(5) 0.55980(3) 0.63073(2) 0.0230(2) Uani 1 1 d G . . . .
H12 H 0.341813 0.505891 0.686421 0.028 Uiso 1 1 calc R U . . .
C10 C 0.66943(5) 0.62390(4) 0.50770(2) 0.0229(2) Uani 1 1 d G . . . .
H10 H 0.828554 0.612518 0.480037 0.027 Uiso 1 1 calc R U . . .
C6 C -0.30496(5) 1.01765(3) 0.40153(2) 0.0233(2) Uani 1 1 d G . . . .
H6 H -0.347160 0.958137 0.454105 0.028 Uiso 1 1 calc R U . . .
C2 C -0.41529(6) 1.20341(3) 0.28387(2) 0.0239(2) Uani 1 1 d G . . . .
C5 C -0.06575(6) 1.00414(3) 0.36424(2) 0.0224(2) Uani 1 1 d G . . . .
C3 C -0.17777(7) 1.19091(3) 0.24572(2) 0.0262(2) Uani 1 1 d G . . . .
H3 H -0.135772 1.250279 0.193040 0.031 Uiso 1 1 calc R U . . .
C4 C -0.00409(6) 1.09019(4) 0.28614(2) 0.0251(2) Uani 1 1 d G . . . .
H4 H 0.157079 1.080006 0.260441 0.030 Uiso 1 1 calc R U . . .
C16 C 1.00752(6) 0.17480(3) 0.80751(2) 0.0249(2) Uani 1 1 d G . . . .
H16A H 0.896494 0.120747 0.807511 0.030 Uiso 1 1 calc R U . . .
H16B H 0.948415 0.215004 0.856244 0.030 Uiso 1 1 calc R U . . .
C1 C -0.59853(7) 1.30558(3) 0.24366(3) 0.0278(3) Uani 1 1 d G . . . .
C8 C 0.25900(5) 0.73826(2) 0.50813(2) 0.0216(2) Uani 1 1 d G . . . .
C15 C 1.00876(5) 0.27947(3) 0.72203(2) 0.0247(2) Uani 1 1 d G . . . .
H15A H 1.115547 0.335070 0.723268 0.030 Uiso 1 1 calc R U . . .
H15B H 1.075236 0.238922 0.673810 0.030 Uiso 1 1 calc R U . . .
C18 C 1.26066(7) -0.01770(3) 0.90476(2) 0.0259(2) Uani 1 1 d G . . . .
H18A H 1.146897 -0.070067 0.904443 0.031 Uiso 1 1 calc R U . . .
H18B H 1.206577 0.019560 0.955022 0.031 Uiso 1 1 calc R U . . .
C19 C 1.50832(7) -0.10439(3) 0.91607(2) 0.0256(2) Uani 1 1 d G . . . .
H19A H 1.564083 -0.139626 0.864964 0.031 Uiso 1 1 calc R U . . .
H19B H 1.621000 -0.052285 0.917861 0.031 Uiso 1 1 calc R U . . .
C20 C 1.51373(8) -0.21452(4) 0.99769(3) 0.0288(3) Uani 1 1 d G . . . .
H20A H 1.398295 -0.265433 0.996501 0.035 Uiso 1 1 calc R U . . .
H20B H 1.461305 -0.179190 1.048848 0.035 Uiso 1 1 calc R U . . .
C17 C 1.25592(6) 0.09044(3) 0.82149(2) 0.0253(2) Uani 1 1 d G . . . .
H17A H 1.316615 0.053105 0.771494 0.030 Uiso 1 1 calc R U . . .
H17B H 1.365138 0.144622 0.822964 0.030 Uiso 1 1 calc R U . . .
C14 C 0.76511(5) 0.36140(3) 0.70415(2) 0.0241(2) Uani 1 1 d G . . . .
H14A H 0.655676 0.308598 0.700640 0.029 Uiso 1 1 calc R U . . .
H14B H 0.696052 0.405245 0.750591 0.029 Uiso 1 1 calc R U . . .
C21 C 1.76015(8) -0.30319(4) 1.00825(3) 0.0338(3) Uani 1 1 d G . . . .
H21A H 1.812194 -0.339509 0.957518 0.041 Uiso 1 1 calc R U . . .
H21B H 1.876206 -0.252426 1.009087 0.041 Uiso 1 1 calc R U . . .
C22 C 1.76237(9) -0.41259(4) 1.09110(3) 0.0469(4) Uani 1 1 d G . . . .
H22A H 1.650509 -0.464432 1.090065 0.070 Uiso 1 1 calc R U . . .
H22B H 1.714282 -0.377283 1.141667 0.070 Uiso 1 1 calc R U . . .
H22C H 1.923744 -0.466346 1.094800 0.070 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 C11 1.3435 . ?
O1 C14 1.4369 . ?
N3 N2 1.2644 . ?
N3 C8 1.4107 . ?
N2 C5 1.4201 . ?
N1 C1 1.1383 . ?
C9 H9 0.9500 . ?
C9 C10 1.3649 . ?
C9 C8 1.4083 . ?
C13 H13 0.9500 . ?
C13 C12 1.3830 . ?
C13 C8 1.3990 . ?
C11 C12 1.4039 . ?
C11 C10 1.4059 . ?
C7 H7 0.9500 . ?
C7 C6 1.3624 . ?
C7 C2 1.4126 . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.4061 . ?
C2 C3 1.4016 . ?
C2 C1 1.4342 . ?
C5 C4 1.3966 . ?
C3 H3 0.9500 . ?
C3 C4 1.3935 . ?
C4 H4 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.5268 . ?
C16 C17 1.5270 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.5054 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5275 . ?
C18 C17 1.5217 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5163 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5288 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5253 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C11 O1 C14 119.4 . . ?
N2 N3 C8 113.5 . . ?
N3 N2 C5 113.6 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C8 121.1 . . ?
C8 C13 H13 119.5 . . ?
O1 C11 C12 125.6 . . ?
O1 C11 C10 114.6 . . ?
C12 C11 C10 119.8 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.1 . . ?
C2 C7 H7 120.0 . . ?
C13 C12 C11 119.3 . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C9 C10 C11 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C2 C1 119.3 . . ?
C3 C2 C7 120.3 . . ?
C3 C2 C1 120.5 . . ?
C6 C5 N2 124.9 . . ?
C4 C5 N2 115.2 . . ?
C4 C5 C6 119.9 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3 . . ?
C3 C4 H4 119.8 . . ?
H16A C16 H16B 107.9 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 111.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
N1 C1 C2 179.3 . . ?
C9 C8 N3 124.9 . . ?
C13 C8 N3 116.2 . . ?
C13 C8 C9 118.9 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C14 C15 C16 113.5 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 112.9 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.3 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C19 C20 C21 113.5 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 C16 113.5 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O1 C14 C15 105.4 . . ?
O1 C14 H14A 110.7 . . ?
O1 C14 H14B 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.7 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 C11 C12 C13 179.9 . . . . ?
O1 C11 C10 C9 -179.6 . . . . ?
N3 N2 C5 C6 -5.6 . . . . ?
N3 N2 C5 C4 175.1 . . . . ?
N2 N3 C8 C9 0.9 . . . . ?
N2 N3 C8 C13 -179.4 . . . . ?
N2 C5 C4 C3 -179.6 . . . . ?
C11 O1 C14 C15 -178.5 . . . . ?
C7 C6 C5 N2 179.7 . . . . ?
C7 C6 C5 C4 -1.1 . . . . ?
C7 C2 C3 C4 0.6 . . . . ?
C12 C13 C8 N3 -178.0 . . . . ?
C12 C13 C8 C9 1.8 . . . . ?
C12 C11 C10 C9 -0.4 . . . . ?
C10 C9 C8 N3 178.4 . . . . ?
C10 C9 C8 C13 -1.3 . . . . ?
C10 C11 C12 C13 0.8 . . . . ?
C6 C7 C2 C3 -0.6 . . . . ?
C6 C7 C2 C1 179.7 . . . . ?
C6 C5 C4 C3 1.2 . . . . ?
C2 C7 C6 C5 0.8 . . . . ?
C2 C3 C4 C5 -0.9 . . . . ?
C16 C15 C14 O1 179.9 . . . . ?
C1 C2 C3 C4 -179.6 . . . . ?
C8 N3 N2 C5 179.9 . . . . ?
C8 C9 C10 C11 0.7 . . . . ?
C8 C13 C12 C11 -1.5 . . . . ?
C15 C16 C17 C18 -178.2 . . . . ?
C18 C19 C20 C21 178.7 . . . . ?
C19 C18 C17 C16 177.7 . . . . ?
C19 C20 C21 C22 179.5 . . . . ?
C17 C16 C15 C14 177.7 . . . . ?
C17 C18 C19 C20 -178.5 . . . . ?
C14 O1 C11 C12 3.2 . . . . ?
C14 O1 C11 C10 -177.5 . . . . ?

_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_AZN-10
_database_code_depnum_ccdc_archive 'CCDC 2457154'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Azonitrile
_chemical_name_systematic        
(E)-4-((4-decyloxyphenyl)diazenyl)benzonitrile
_chemical_formula_moiety         'C23 H29 N3 O'
_chemical_formula_sum            'C23 H29 N3 O'
_chemical_formula_weight         363.49
_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 0.0033 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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.7970(12)
_cell_length_b                   7.4060(15)
_cell_length_c                   46.464(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.23(3)
_cell_angle_gamma                90
_cell_volume                     1991.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      0.9
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      1.21
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            28653
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         27.800
_diffrn_reflns_theta_min         0.865
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4423
_reflns_number_total             4856
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0945P)²+2.7855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2114
_refine_ls_wR_factor_ref         0.2135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 O1(N2,N3,N1,C13,C3,C6,C5,C4,C8,C2,C12,C9,C7,C10,C11,C1,C21,C20,C22,C18,C14,
 C19,C16,C15,C17,C23)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C20(H20A,H20B), C22(H22A,H22B), C18(H18A,H18B), C14(H14A,
 H14B), C19(H19A,H19B), C16(H16B,H16A), C15(H15B,H15A), C17(H17B,H17A)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C6(H6), C4(H4), C12(H12), C9(H9), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C23(H23C,H23B,H23A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.36221(8) 0.51521(7) 0.40305(2) 0.0209(3) Uani 1 1 d G . . . .
N2 N 0.96783(7) 0.73253(6) 0.51183(2) 0.0177(3) Uani 1 1 d G . . . .
N3 N 1.01655(6) 0.76242(6) 0.48578(2) 0.0178(3) Uani 1 1 d G . . . .
N1 N 1.75623(11) 1.01445(10) 0.61534(2) 0.0289(4) Uani 1 1 d G . . . .
C13 C 0.63721(8) 0.62099(8) 0.47255(2) 0.0174(3) Uani 1 1 d G . . . .
H13 H 0.605185 0.607710 0.492267 0.021 Uiso 1 1 calc R U . . .
C3 C 1.50582(9) 0.92876(10) 0.54690(2) 0.0186(4) Uani 1 1 d G . . . .
H3 H 1.648504 0.981080 0.542195 0.022 Uiso 1 1 calc R U . . .
C6 C 1.08925(8) 0.77407(9) 0.56137(2) 0.0184(4) Uani 1 1 d G . . . .
H6 H 0.946793 0.721722 0.566160 0.022 Uiso 1 1 calc R U . . .
C5 C 1.13991(7) 0.79614(6) 0.53256(2) 0.0173(4) Uani 1 1 d G . . . .
C4 C 1.34691(8) 0.87441(8) 0.52535(2) 0.0183(4) Uani 1 1 d G . . . .
H4 H 1.378954 0.890453 0.505688 0.022 Uiso 1 1 calc R U . . .
C8 C 0.84472(6) 0.69876(5) 0.46521(2) 0.0167(3) Uani 1 1 d G . . . .
C2 C 1.45414(9) 0.90583(7) 0.57579(2) 0.0186(4) Uani 1 1 d G . . . .
C12 C 0.47843(8) 0.56333(9) 0.45141(2) 0.0182(4) Uani 1 1 d G . . . .
H12 H 0.336157 0.511685 0.456428 0.022 Uiso 1 1 calc R U . . .
C9 C 0.89347(6) 0.71690(8) 0.43631(2) 0.0183(4) Uani 1 1 d G . . . .
H9 H 1.035820 0.768510 0.431316 0.022 Uiso 1 1 calc R U . . .
C7 C 1.24843(9) 0.82915(9) 0.58286(2) 0.0194(4) Uani 1 1 d G . . . .
H7 H 1.215877 0.814093 0.602528 0.023 Uiso 1 1 calc R U . . .
C10 C 0.73357(6) 0.65939(7) 0.41478(2) 0.0188(4) Uani 1 1 d G . . . .
H10 H 0.765039 0.673540 0.395063 0.023 Uiso 1 1 calc R U . . .
C11 C 0.52889(7) 0.58163(5) 0.42226(2) 0.0181(4) Uani 1 1 d G . . . .
C1 C 1.62170(10) 0.96590(9) 0.59799(2) 0.0206(4) Uani 1 1 d G . . . .
C21 C -0.50922(12) 0.42502(11) 0.21233(2) 0.0233(4) Uani 1 1 d G . . . .
H21A H -0.501547 0.291546 0.211717 0.028 Uiso 1 1 calc R U . . .
H21B H -0.647757 0.458834 0.222633 0.028 Uiso 1 1 calc R U . . .
C20 C -0.29406(12) 0.49691(10) 0.22913(2) 0.0235(4) Uani 1 1 d G . . . .
H20A H -0.155552 0.463608 0.218785 0.028 Uiso 1 1 calc R U . . .
H20B H -0.302087 0.630353 0.229835 0.028 Uiso 1 1 calc R U . . .
C22 C -0.53474(14) 0.49731(12) 0.18158(2) 0.0264(4) Uani 1 1 d G . . . .
H22A H -0.396200 0.463896 0.171250 0.032 Uiso 1 1 calc R U . . .
H22B H -0.543543 0.630750 0.182147 0.032 Uiso 1 1 calc R U . . .
C18 C -0.05153(9) 0.49637(9) 0.27672(2) 0.0235(4) Uani 1 1 d G . . . .
H18A H 0.087345 0.457477 0.266914 0.028 Uiso 1 1 calc R U . . .
H18B H -0.055672 0.630000 0.276482 0.028 Uiso 1 1 calc R U . . .
C14 C 0.39466(7) 0.53504(6) 0.37296(2) 0.0218(4) Uani 1 1 d G . . . .
H14A H 0.532575 0.466549 0.367633 0.026 Uiso 1 1 calc R U . . .
H14B H 0.417686 0.663841 0.368196 0.026 Uiso 1 1 calc R U . . .
C19 C -0.26812(10) 0.42364(9) 0.25989(2) 0.0237(4) Uani 1 1 d G . . . .
H19A H -0.259902 0.290202 0.259201 0.028 Uiso 1 1 calc R U . . .
H19B H -0.406579 0.456910 0.270250 0.028 Uiso 1 1 calc R U . . .
C16 C 0.18062(8) 0.50603(7) 0.32461(2) 0.0227(4) Uani 1 1 d G . . . .
H16B H 0.186056 0.638603 0.322005 0.027 Uiso 1 1 calc R U . . .
H16A H 0.321009 0.454230 0.316654 0.027 Uiso 1 1 calc R U . . .
C15 C 0.18180(8) 0.46336(7) 0.35674(2) 0.0234(4) Uani 1 1 d G . . . .
H15B H 0.043047 0.517061 0.364822 0.028 Uiso 1 1 calc R U . . .
H15A H 0.174027 0.330902 0.359385 0.028 Uiso 1 1 calc R U . . .
C17 C -0.03155(9) 0.43170(8) 0.30786(2) 0.0240(4) Uani 1 1 d G . . . .
H17B H -0.171557 0.468901 0.317586 0.029 Uiso 1 1 calc R U . . .
H17A H -0.024855 0.298133 0.308099 0.029 Uiso 1 1 calc R U . . .
C23 C -0.75026(14) 0.42348(13) 0.16500(2) 0.0307(5) Uani 1 1 d G . . . .
H23C H -0.755062 0.467979 0.145113 0.046 Uiso 1 1 calc R U . . .
H23B H -0.888650 0.463994 0.174324 0.046 Uiso 1 1 calc R U . . .
H23A H -0.744994 0.291221 0.164956 0.046 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 C11 1.3694 . ?
O1 C14 1.4287 . ?
N2 N3 1.2776 . ?
N2 C5 1.4271 . ?
N3 C8 1.4215 . ?
N1 C1 1.1474 . ?
C13 H13 0.9500 . ?
C13 C8 1.3933 . ?
C13 C12 1.3757 . ?
C3 H3 0.9500 . ?
C3 C4 1.3818 . ?
C3 C2 1.4021 . ?
C6 H6 0.9500 . ?
C6 C5 1.3961 . ?
C6 C7 1.3824 . ?
C5 C4 1.3905 . ?
C4 H4 0.9500 . ?
C8 C9 1.3942 . ?
C2 C7 1.3772 . ?
C2 C1 1.4466 . ?
C12 H12 0.9500 . ?
C12 C11 1.4082 . ?
C9 H9 0.9500 . ?
C9 C10 1.3917 . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.3809 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.5293 . ?
C21 C22 1.5251 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C19 1.5283 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5313 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5387 . ?
C18 C17 1.5223 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5059 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 C15 1.5256 . ?
C16 C17 1.5211 . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 H17A 0.9900 . ?
C23 H23C 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23A 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
C11 O1 C14 118.3 . . ?
N3 N2 C5 113.5 . . ?
N2 N3 C8 113.3 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C8 120.4 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.3 . . ?
C2 C3 H3 120.4 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.3 . . ?
C6 C5 N2 115.6 . . ?
C4 C5 N2 123.7 . . ?
C4 C5 C6 120.7 . . ?
C3 C4 C5 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C13 C8 N3 123.7 . . ?
C13 C8 C9 120.0 . . ?
C9 C8 N3 116.3 . . ?
C3 C2 C1 118.3 . . ?
C7 C2 C3 120.9 . . ?
C7 C2 C1 120.8 . . ?
C13 C12 H12 120.3 . . ?
C13 C12 C11 119.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.1 . . ?
C2 C7 H7 120.0 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6 . . ?
C11 C10 H10 120.2 . . ?
O1 C11 C12 114.5 . . ?
O1 C11 C10 124.8 . . ?
C10 C11 C12 120.7 . . ?
N1 C1 C2 179.1 . . ?
H21A C21 H21B 107.8 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C22 C21 C20 112.9 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C19 C20 C21 112.8 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C21 C22 C23 112.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 112.9 . . ?
O1 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
O1 C14 C15 107.7 . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
C20 C19 C18 112.7 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
H16B C16 H16A 107.8 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 C15 112.6 . . ?
C14 C15 C16 112.0 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C16 C15 H15A 109.2 . . ?
H15B C15 H15A 107.9 . . ?
C18 C17 H17B 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 C18 112.9 . . ?
C16 C17 H17B 109.0 . . ?
C16 C17 H17A 109.0 . . ?
H17B C17 H17A 107.8 . . ?
C22 C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23B C23 H23A 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
O1 C14 C15 C16 170.6 . . . . ?
N2 N3 C8 C13 3.6 . . . . ?
N2 N3 C8 C9 -176.2 . . . . ?
N2 C5 C4 C3 -178.6 . . . . ?
N3 N2 C5 C6 177.1 . . . . ?
N3 N2 C5 C4 -3.3 . . . . ?
N3 C8 C9 C10 -179.5 . . . . ?
C13 C8 C9 C10 0.8 . . . . ?
C13 C12 C11 O1 178.2 . . . . ?
C13 C12 C11 C10 -1.1 . . . . ?
C3 C2 C7 C6 -0.2 . . . . ?
C6 C5 C4 C3 0.9 . . . . ?
C5 N2 N3 C8 180.0 . . . . ?
C5 C6 C7 C2 0.3 . . . . ?
C4 C3 C2 C7 0.4 . . . . ?
C4 C3 C2 C1 -179.2 . . . . ?
C8 C13 C12 C11 0.8 . . . . ?
C8 C9 C10 C11 -1.1 . . . . ?
C2 C3 C4 C5 -0.7 . . . . ?
C12 C13 C8 N3 179.6 . . . . ?
C12 C13 C8 C9 -0.6 . . . . ?
C9 C10 C11 O1 -177.9 . . . . ?
C9 C10 C11 C12 1.3 . . . . ?
C7 C6 C5 N2 178.9 . . . . ?
C7 C6 C5 C4 -0.7 . . . . ?
C11 O1 C14 C15 -176.1 . . . . ?
C1 C2 C7 C6 179.4 . . . . ?
C21 C20 C19 C18 -180.0 . . . . ?
C20 C21 C22 C23 179.7 . . . . ?
C22 C21 C20 C19 -179.7 . . . . ?
C14 O1 C11 C12 177.4 . . . . ?
C14 O1 C11 C10 -3.3 . . . . ?
C19 C18 C17 C16 -179.1 . . . . ?
C15 C16 C17 C18 171.7 . . . . ?
C17 C18 C19 C20 177.0 . . . . ?
C17 C16 C15 C14 179.0 . . . . ?

_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_AZN-3
_database_code_depnum_ccdc_archive 'CCDC 2457153'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Azonitrile
_chemical_name_systematic        (E)-4-((4-propoxyphenyl)diazenyl)benzonitrile
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_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 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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                   5.9500(12)
_cell_length_b                   18.537(4)
_cell_length_c                   19.114(4)
_cell_angle_alpha                73.39(3)
_cell_angle_beta                 87.85(3)
_cell_angle_gamma                88.91(3)
_cell_volume                     2018.7(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    11765
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      1.1
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      1.31
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35341
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.749
_diffrn_reflns_theta_min         1.096
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10388
_reflns_number_total             11765
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.473
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         11765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.045
_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)+(0.1331P)²+0.2051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(O4)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=1-FVAR(1)
 Sof(O3)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C14(H14A,
 H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B)
3.b Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C49(H49A,H49B,H49C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C34(H34),
  C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.10012(10) 0.15957(3) 0.01778(3) 0.02508(14) Uani 1 1 d . . . . .
O2 O -0.13024(10) 0.47364(4) 0.29982(3) 0.02564(14) Uani 1 1 d . . . . .
O3 O -0.0472(3) 0.17000(11) 0.64092(10) 0.0297(4) Uani 0.531(3) 1 d . . P A 1
C46 C 0.0285(4) 0.21809(12) 0.68178(12) 0.0364(5) Uani 0.531(3) 1 d . . P A 1
H46A H 0.066224 0.268288 0.648469 0.044 Uiso 0.531(3) 1 calc R U P A 1
H46B H 0.164842 0.196397 0.708381 0.044 Uiso 0.531(3) 1 calc R U P A 1
C47 C -0.1583(4) 0.22520(12) 0.73520(11) 0.0409(6) Uani 0.531(3) 1 d . . P A 1
H47A H -0.207261 0.174159 0.763668 0.049 Uiso 0.531(3) 1 calc R U P A 1
H47B H -0.099149 0.250320 0.769868 0.049 Uiso 0.531(3) 1 calc R U P A 1
C51 C -0.3543(6) 0.2679(2) 0.69992(15) 0.0814(13) Uani 0.531(3) 1 d . . P A 1
H51A H -0.469105 0.270548 0.737284 0.122 Uiso 0.531(3) 1 calc R U P A 1
H51B H -0.308207 0.318993 0.672587 0.122 Uiso 0.531(3) 1 calc R U P A 1
H51C H -0.416405 0.242771 0.666382 0.122 Uiso 0.531(3) 1 calc R U P A 1
C48 C -0.2693(3) 0.21684(12) 0.70238(12) 0.0333(5) Uani 0.469(3) 1 d . . P A 2
H48A H -0.395324 0.228972 0.668439 0.040 Uiso 0.469(3) 1 calc R U P A 2
H48B H -0.304416 0.168984 0.740085 0.040 Uiso 0.469(3) 1 calc R U P A 2
C49 C -0.2470(5) 0.27852(17) 0.73831(18) 0.0533(8) Uani 0.469(3) 1 d . . P A 2
H49A H -0.387789 0.283526 0.764880 0.080 Uiso 0.469(3) 1 calc R U P A 2
H49B H -0.123916 0.266162 0.772527 0.080 Uiso 0.469(3) 1 calc R U P A 2
H49C H -0.214730 0.326089 0.700954 0.080 Uiso 0.469(3) 1 calc R U P A 2
O4 O -0.0960(3) 0.15126(12) 0.62452(10) 0.0268(4) Uani 0.469(3) 1 d . . P A 2
C50 C -0.0556(4) 0.20725(12) 0.66077(13) 0.0272(4) Uani 0.469(3) 1 d . . P A 2
H50A H -0.014286 0.255494 0.624609 0.033 Uiso 0.469(3) 1 calc R U P A 2
H50B H 0.069270 0.191091 0.694748 0.033 Uiso 0.469(3) 1 calc R U P A 2
N1 N 0.53556(12) 0.26193(4) 0.25255(4) 0.02114(14) Uani 1 1 d . . . . .
N2 N 0.47525(12) 0.21598(4) 0.21947(4) 0.02119(14) Uani 1 1 d . . . . .
N3 N -0.20970(14) 0.33428(5) 0.50147(5) 0.03692(19) Uani 1 1 d . . . . .
N4 N 0.47342(12) 0.38718(4) 0.06444(4) 0.02255(15) Uani 1 1 d . . . . .
N5 N 0.51994(12) 0.43472(4) 0.09759(4) 0.02232(15) Uani 1 1 d . . . . .
N6 N 1.24470(14) 0.34510(5) -0.19108(5) 0.03672(19) Uani 1 1 d . . . . .
N7 N 0.46016(13) 0.05327(4) 0.39508(4) 0.02975(17) Uani 1 1 d . . . . .
N8 N 0.52338(13) 0.10076(5) 0.42566(4) 0.02744(16) Uani 1 1 d . . . . .
N9 N 1.19195(17) -0.02233(6) 0.14412(5) 0.0435(2) Uani 1 1 d . . . . .
C1 C 0.37080(13) 0.27388(4) 0.30436(4) 0.02006(15) Uani 1 1 d . . . . .
C2 C 0.16211(13) 0.23860(4) 0.31809(4) 0.02201(16) Uani 1 1 d . . . . .
H2 H 0.122963 0.204004 0.292345 0.026 Uiso 1 1 calc R U . . .
C3 C 0.01209(13) 0.25397(5) 0.36916(4) 0.02313(16) Uani 1 1 d . . . . .
H3 H -0.130433 0.230239 0.378552 0.028 Uiso 1 1 calc R U . . .
C4 C 0.07270(14) 0.30489(5) 0.40685(4) 0.02313(16) Uani 1 1 d . . . . .
C5 C 0.28148(14) 0.34005(5) 0.39353(4) 0.02412(16) Uani 1 1 d . . . . .
H5 H 0.321436 0.374282 0.419586 0.029 Uiso 1 1 calc R U . . .
C6 C 0.43070(13) 0.32462(4) 0.34182(4) 0.02230(16) Uani 1 1 d . . . . .
H6 H 0.572873 0.348562 0.332078 0.027 Uiso 1 1 calc R U . . .
C7 C 0.63779(13) 0.20379(4) 0.16792(4) 0.01984(15) Uani 1 1 d . . . . .
C8 C 0.57762(13) 0.15481(4) 0.12861(4) 0.02247(16) Uani 1 1 d . . . . .
H8 H 0.433725 0.131985 0.137121 0.027 Uiso 1 1 calc R U . . .
C9 C 0.72681(14) 0.13905(5) 0.07695(4) 0.02375(16) Uani 1 1 d . . . . .
H9 H 0.684488 0.106017 0.049894 0.029 Uiso 1 1 calc R U . . .
C10 C 0.93856(13) 0.17202(4) 0.06515(4) 0.02110(15) Uani 1 1 d . . . . .
C11 C 0.99904(13) 0.22202(4) 0.10427(4) 0.02088(15) Uani 1 1 d . . . . .
H11 H 1.142543 0.245114 0.095657 0.025 Uiso 1 1 calc R U . . .
C12 C 0.84994(13) 0.23747(4) 0.15509(4) 0.02067(15) Uani 1 1 d . . . . .
H12 H 0.891207 0.271150 0.181586 0.025 Uiso 1 1 calc R U . . .
C13 C -0.08356(15) 0.32119(5) 0.45963(5) 0.02782(18) Uani 1 1 d . . . . .
C14 C 1.05475(14) 0.10573(5) -0.02095(5) 0.02779(17) Uani 1 1 d . . . . .
H14A H 0.945552 0.126993 -0.059481 0.033 Uiso 1 1 calc R U . . .
H14B H 0.990106 0.059500 0.013053 0.033 Uiso 1 1 calc R U . . .
C15 C 1.27409(14) 0.08757(5) -0.05464(5) 0.02707(17) Uani 1 1 d . . . . .
H15A H 1.247014 0.048618 -0.079525 0.032 Uiso 1 1 calc R U . . .
H15B H 1.380280 0.066103 -0.015212 0.032 Uiso 1 1 calc R U . . .
C16 C 1.38216(18) 0.15495(5) -0.10907(6) 0.0389(2) Uani 1 1 d . . . . .
H16A H 1.280475 0.175558 -0.149260 0.058 Uiso 1 1 calc R U . . .
H16B H 1.523948 0.139360 -0.128409 0.058 Uiso 1 1 calc R U . . .
H16C H 1.411987 0.193546 -0.084754 0.058 Uiso 1 1 calc R U . . .
C17 C 0.64472(13) 0.37943(4) 0.01283(4) 0.02165(16) Uani 1 1 d . . . . .
C18 C 0.84893(14) 0.41745(5) 0.00198(4) 0.02360(16) Uani 1 1 d . . . . .
H18 H 0.880755 0.450539 0.030132 0.028 Uiso 1 1 calc R U . . .
C19 C 1.00515(14) 0.40694(5) -0.04978(4) 0.02436(17) Uani 1 1 d . . . . .
H19 H 1.144772 0.432504 -0.057212 0.029 Uiso 1 1 calc R U . . .
C20 C 0.95547(14) 0.35833(5) -0.09105(4) 0.02436(17) Uani 1 1 d . . . . .
C21 C 0.75216(15) 0.31974(5) -0.08002(5) 0.02658(17) Uani 1 1 d . . . . .
H21 H 0.720217 0.286608 -0.108116 0.032 Uiso 1 1 calc R U . . .
C22 C 0.59702(14) 0.33018(5) -0.02765(5) 0.02488(17) Uani 1 1 d . . . . .
H22 H 0.458688 0.303822 -0.019410 0.030 Uiso 1 1 calc R U . . .
C23 C 0.35081(13) 0.44328(4) 0.14879(4) 0.02048(15) Uani 1 1 d . . . . .
C24 C 0.14483(13) 0.40544(4) 0.15994(4) 0.02211(16) Uani 1 1 d . . . . .
H24 H 0.113354 0.371502 0.132645 0.027 Uiso 1 1 calc R U . . .
C25 C -0.01182(13) 0.41743(4) 0.21042(4) 0.02226(16) Uani 1 1 d . . . . .
H25 H -0.152004 0.392227 0.217530 0.027 Uiso 1 1 calc R U . . .
C26 C 0.03566(14) 0.46689(5) 0.25135(4) 0.02205(16) Uani 1 1 d . . . . .
C27 C 0.24050(14) 0.50473(5) 0.24048(4) 0.02361(16) Uani 1 1 d . . . . .
H27 H 0.272654 0.538393 0.268000 0.028 Uiso 1 1 calc R U . . .
C28 C 0.39713(14) 0.49264(5) 0.18894(4) 0.02329(16) Uani 1 1 d . . . . .
H28 H 0.536578 0.518316 0.181191 0.028 Uiso 1 1 calc R U . . .
C29 C 1.11572(15) 0.35019(5) -0.14645(5) 0.02788(18) Uani 1 1 d . . . . .
C30 C -0.09347(15) 0.52170(5) 0.34506(5) 0.02683(17) Uani 1 1 d . . . . .
H30A H -0.046335 0.572224 0.314646 0.032 Uiso 1 1 calc R U . . .
H30B H 0.026237 0.500398 0.379847 0.032 Uiso 1 1 calc R U . . .
C31 C -0.31150(15) 0.52728(5) 0.38587(5) 0.03169(19) Uani 1 1 d . . . . .
H31A H -0.364113 0.476024 0.412197 0.038 Uiso 1 1 calc R U . . .
H31B H -0.426892 0.551736 0.350573 0.038 Uiso 1 1 calc R U . . .
C32 C -0.2853(2) 0.57205(7) 0.44003(7) 0.0458(3) Uani 1 1 d . . . . .
H32A H -0.223822 0.621688 0.414609 0.069 Uiso 1 1 calc R U . . .
H32B H -0.182741 0.545261 0.477958 0.069 Uiso 1 1 calc R U . . .
H32C H -0.432402 0.578175 0.462567 0.069 Uiso 1 1 calc R U . . .
C33 C 0.62155(15) 0.03957(5) 0.34321(5) 0.02688(18) Uani 1 1 d . . . . .
C34 C 0.83217(15) 0.07358(5) 0.32866(5) 0.02667(17) Uani 1 1 d . . . . .
H34 H 0.875061 0.107889 0.354259 0.032 Uiso 1 1 calc R U . . .
C35 C 0.97847(15) 0.05751(5) 0.27715(5) 0.02669(17) Uani 1 1 d . . . . .
H35 H 1.121821 0.080625 0.267135 0.032 Uiso 1 1 calc R U . . .
C36 C 0.91317(16) 0.00678(5) 0.23986(5) 0.02882(18) Uani 1 1 d . . . . .
C37 C 0.70319(17) -0.02741(5) 0.25427(6) 0.0342(2) Uani 1 1 d . . . . .
H37 H 0.659927 -0.061578 0.228563 0.041 Uiso 1 1 calc R U . . .
C38 C 0.55767(16) -0.01128(5) 0.30635(6) 0.0324(2) Uani 1 1 d . . . . .
H38 H 0.414998 -0.034819 0.316851 0.039 Uiso 1 1 calc R U . . .
C39 C 0.36613(14) 0.11519(5) 0.47748(5) 0.0303(2) Uani 1 1 d . . . . .
C40 C 0.15339(16) 0.08198(7) 0.49343(6) 0.0415(3) Uani 1 1 d . . . . .
H40 H 0.106559 0.047833 0.468186 0.050 Uiso 1 1 calc R U . . .
C41 C 0.01237(17) 0.09861(8) 0.54543(7) 0.0519(4) Uani 1 1 d . . . . .
H41 H -0.131240 0.075778 0.556285 0.062 Uiso 1 1 calc R U . . .
C42 C 0.08106(19) 0.14946(8) 0.58251(6) 0.0506(4) Uani 1 1 d . . . . .
C43 C 0.28892(19) 0.18360(7) 0.56598(6) 0.0430(3) Uani 1 1 d . . . . .
H43 H 0.334199 0.218843 0.590201 0.052 Uiso 1 1 calc R U . . .
C44 C 0.43135(16) 0.16591(6) 0.51356(5) 0.0328(2) Uani 1 1 d . . . . .
H44 H 0.574663 0.188923 0.502479 0.039 Uiso 1 1 calc R U . . .
C45 C 1.06728(18) -0.00951(6) 0.18634(6) 0.0339(2) 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
O1 C10 1.3576(10) . ?
O1 C14 1.4368(10) . ?
O2 C26 1.3569(10) . ?
O2 C30 1.4323(10) . ?
O3 C46 1.431(3) . ?
O3 C42 1.464(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.511(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C51 1.470(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.503(3) . ?
C48 C50 1.509(3) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
O4 C50 1.431(3) . ?
O4 C42 1.3060(19) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
N1 N2 1.2612(10) . ?
N1 C1 1.4266(10) . ?
N2 C7 1.4159(11) . ?
N3 C13 1.1493(12) . ?
N4 N5 1.2636(11) . ?
N4 C17 1.4257(11) . ?
N5 C23 1.4158(11) . ?
N6 C29 1.1488(12) . ?
N7 N8 1.2575(13) . ?
N7 C33 1.4257(13) . ?
N8 C39 1.4144(12) . ?
N9 C45 1.1472(15) . ?
C1 C2 1.3952(12) . ?
C1 C6 1.3934(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.3837(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.4005(12) . ?
C4 C5 1.3946(12) . ?
C4 C13 1.4375(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.3904(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.3927(11) . ?
C7 C12 1.4010(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.3921(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.3931(12) . ?
C10 C11 1.4059(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.3776(11) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5085(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5144(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3950(12) . ?
C17 C22 1.3939(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.3839(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.3984(12) . ?
C20 C21 1.3954(13) . ?
C20 C29 1.4364(12) . ?
C21 H21 0.9500 . ?
C21 C22 1.3879(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.4026(12) . ?
C23 C28 1.3889(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.3771(11) . ?
C25 H25 0.9500 . ?
C25 C26 1.4032(12) . ?
C26 C27 1.3967(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.3924(11) . ?
C28 H28 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.5058(12) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.5142(13) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.3961(13) . ?
C33 C38 1.3939(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.3819(13) . ?
C35 H35 0.9500 . ?
C35 C36 1.4003(12) . ?
C36 C37 1.3939(14) . ?
C36 C45 1.4403(14) . ?
C37 H37 0.9500 . ?
C37 C38 1.3878(15) . ?
C38 H38 0.9500 . ?
C39 C40 1.4027(14) . ?
C39 C44 1.3839(16) . ?
C40 H40 0.9500 . ?
C40 C41 1.3747(17) . ?
C41 H41 0.9500 . ?
C41 C42 1.406(2) . ?
C42 C43 1.3842(19) . ?
C43 H43 0.9500 . ?
C43 C44 1.3941(14) . ?
C44 H44 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
C10 O1 C14 117.93(7) . . ?
C26 O2 C30 118.35(7) . . ?
C46 O3 C42 125.77(17) . . ?
O3 C46 H46A 110.1 . . ?
O3 C46 H46B 110.1 . . ?
O3 C46 C47 108.08(19) . . ?
H46A C46 H46B 108.4 . . ?
C47 C46 H46A 110.1 . . ?
C47 C46 H46B 110.1 . . ?
C46 C47 H47A 108.9 . . ?
C46 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
C51 C47 C46 113.40(18) . . ?
C51 C47 H47A 108.9 . . ?
C51 C47 H47B 108.9 . . ?
C47 C51 H51A 109.5 . . ?
C47 C51 H51B 109.5 . . ?
C47 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
H48A C48 H48B 108.0 . . ?
C49 C48 H48A 109.4 . . ?
C49 C48 H48B 109.4 . . ?
C49 C48 C50 111.18(19) . . ?
C50 C48 H48A 109.4 . . ?
C50 C48 H48B 109.4 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C42 O4 C50 106.87(18) . . ?
C48 C50 H50A 110.2 . . ?
C48 C50 H50B 110.2 . . ?
O4 C50 C48 107.6(2) . . ?
O4 C50 H50A 110.2 . . ?
O4 C50 H50B 110.2 . . ?
H50A C50 H50B 108.5 . . ?
N2 N1 C1 113.58(7) . . ?
N1 N2 C7 113.97(7) . . ?
N5 N4 C17 113.34(8) . . ?
N4 N5 C23 113.98(7) . . ?
N8 N7 C33 113.41(8) . . ?
N7 N8 C39 114.45(8) . . ?
C2 C1 N1 124.07(7) . . ?
C6 C1 N1 115.33(7) . . ?
C6 C1 C2 120.60(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(8) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(8) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C13 119.29(8) . . ?
C5 C4 C3 120.87(8) . . ?
C5 C4 C13 119.83(8) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.49(8) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.71(8) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 N2 116.33(7) . . ?
C8 C7 C12 119.58(7) . . ?
C12 C7 N2 124.09(7) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(7) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.60(7) . . ?
C10 C9 H9 120.2 . . ?
O1 C10 C9 125.03(7) . . ?
O1 C10 C11 114.91(7) . . ?
C9 C10 C11 120.05(7) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.91(7) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.36(7) . . ?
C11 C12 H12 119.8 . . ?
N3 C13 C4 179.51(10) . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
O1 C14 C15 107.80(7) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.73(8) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N4 123.89(8) . . ?
C22 C17 N4 115.59(7) . . ?
C22 C17 C18 120.52(8) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.99(8) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.35(8) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C29 118.69(8) . . ?
C21 C20 C19 120.87(8) . . ?
C21 C20 C29 120.43(8) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.43(8) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.82(8) . . ?
C21 C22 H22 120.1 . . ?
C24 C23 N5 123.66(7) . . ?
C28 C23 N5 116.40(7) . . ?
C28 C23 C24 119.94(8) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.06(8) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 119.99(7) . . ?
C26 C25 H25 120.0 . . ?
O2 C26 C25 114.70(7) . . ?
O2 C26 C27 125.10(8) . . ?
C27 C26 C25 120.20(8) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.38(8) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 120.43(8) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
N6 C29 C20 178.72(9) . . ?
O2 C30 H30A 110.2 . . ?
O2 C30 H30B 110.2 . . ?
O2 C30 C31 107.54(7) . . ?
H30A C30 H30B 108.5 . . ?
C31 C30 H30A 110.2 . . ?
C31 C30 H30B 110.2 . . ?
C30 C31 H31A 109.3 . . ?
C30 C31 H31B 109.3 . . ?
C30 C31 C32 111.64(8) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N7 123.87(9) . . ?
C38 C33 N7 115.79(8) . . ?
C38 C33 C34 120.34(9) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.23(9) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.29(8) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C45 118.73(9) . . ?
C37 C36 C35 120.71(9) . . ?
C37 C36 C45 120.56(9) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.66(9) . . ?
C38 C37 H37 120.2 . . ?
C33 C38 H38 120.1 . . ?
C37 C38 C33 119.77(9) . . ?
C37 C38 H38 120.1 . . ?
C40 C39 N8 124.28(11) . . ?
C44 C39 N8 116.25(8) . . ?
C44 C39 C40 119.46(10) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.30(13) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.88(11) . . ?
C42 C41 H41 120.1 . . ?
O4 C42 C41 101.27(15) . . ?
O4 C42 C43 138.55(19) . . ?
C41 C42 O3 125.76(14) . . ?
C43 C42 O3 114.10(17) . . ?
C43 C42 C41 120.12(11) . . ?
C42 C43 H43 120.2 . . ?
C42 C43 C44 119.54(13) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 C43 120.68(10) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
N9 C45 C36 179.25(11) . . ?

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
O1 C10 C11 C12 -178.53(6) . . . . ?
O1 C14 C15 C16 -61.28(10) . . . . ?
O2 C26 C27 C28 179.87(7) . . . . ?
O2 C30 C31 C32 175.41(8) . . . . ?
O3 C46 C47 C51 -69.0(3) . . . . ?
O3 C42 C43 C44 177.10(9) . . . . ?
C46 O3 C42 C41 175.84(14) . . . . ?
C46 O3 C42 C43 -2.6(2) . . . . ?
C49 C48 C50 O4 -176.3(2) . . . . ?
O4 C42 C43 C44 -177.98(15) . . . . ?
C50 O4 C42 C41 -174.61(13) . . . . ?
C50 O4 C42 C43 2.3(2) . . . . ?
N1 N2 C7 C8 -178.57(6) . . . . ?
N1 N2 C7 C12 1.58(11) . . . . ?
N1 C1 C2 C3 -179.64(6) . . . . ?
N1 C1 C6 C5 -179.97(6) . . . . ?
N2 N1 C1 C2 0.11(11) . . . . ?
N2 N1 C1 C6 -179.69(6) . . . . ?
N2 C7 C8 C9 -179.70(6) . . . . ?
N2 C7 C12 C11 179.46(6) . . . . ?
N4 N5 C23 C24 -2.82(12) . . . . ?
N4 N5 C23 C28 177.48(7) . . . . ?
N4 C17 C18 C19 -179.52(6) . . . . ?
N4 C17 C22 C21 179.07(6) . . . . ?
N5 N4 C17 C18 2.98(12) . . . . ?
N5 N4 C17 C22 -177.16(7) . . . . ?
N5 C23 C24 C25 -179.40(6) . . . . ?
N5 C23 C28 C27 179.89(6) . . . . ?
N7 N8 C39 C40 -1.69(13) . . . . ?
N7 N8 C39 C44 178.63(7) . . . . ?
N7 C33 C34 C35 -179.63(7) . . . . ?
N7 C33 C38 C37 179.28(7) . . . . ?
N8 N7 C33 C34 1.64(12) . . . . ?
N8 N7 C33 C38 -178.47(7) . . . . ?
N8 C39 C40 C41 179.15(8) . . . . ?
N8 C39 C44 C43 -179.61(7) . . . . ?
C1 N1 N2 C7 180.00(5) . . . . ?
C1 C2 C3 C4 -0.25(12) . . . . ?
C2 C1 C6 C5 0.22(12) . . . . ?
C2 C3 C4 C5 -0.02(12) . . . . ?
C2 C3 C4 C13 179.66(6) . . . . ?
C3 C4 C5 C6 0.38(12) . . . . ?
C4 C5 C6 C1 -0.48(12) . . . . ?
C6 C1 C2 C3 0.15(12) . . . . ?
C7 C8 C9 C10 0.66(12) . . . . ?
C8 C7 C12 C11 -0.39(12) . . . . ?
C8 C9 C10 O1 178.25(7) . . . . ?
C8 C9 C10 C11 -1.23(12) . . . . ?
C9 C10 C11 C12 1.00(12) . . . . ?
C10 O1 C14 C15 -166.11(7) . . . . ?
C10 C11 C12 C7 -0.19(12) . . . . ?
C12 C7 C8 C9 0.15(12) . . . . ?
C13 C4 C5 C6 -179.30(7) . . . . ?
C14 O1 C10 C9 -3.04(12) . . . . ?
C14 O1 C10 C11 176.46(7) . . . . ?
C17 N4 N5 C23 179.71(5) . . . . ?
C17 C18 C19 C20 0.31(12) . . . . ?
C18 C17 C22 C21 -1.07(13) . . . . ?
C18 C19 C20 C21 -0.81(12) . . . . ?
C18 C19 C20 C29 177.69(7) . . . . ?
C19 C20 C21 C22 0.37(13) . . . . ?
C20 C21 C22 C17 0.57(13) . . . . ?
C22 C17 C18 C19 0.62(12) . . . . ?
C23 C24 C25 C26 -0.74(12) . . . . ?
C24 C23 C28 C27 0.18(12) . . . . ?
C24 C25 C26 O2 -179.39(6) . . . . ?
C24 C25 C26 C27 0.74(12) . . . . ?
C25 C26 C27 C28 -0.27(12) . . . . ?
C26 O2 C30 C31 172.56(7) . . . . ?
C26 C27 C28 C23 -0.19(12) . . . . ?
C28 C23 C24 C25 0.28(12) . . . . ?
C29 C20 C21 C22 -178.11(7) . . . . ?
C30 O2 C26 C25 178.59(6) . . . . ?
C30 O2 C26 C27 -1.54(12) . . . . ?
C33 N7 N8 C39 -179.88(6) . . . . ?
C33 C34 C35 C36 -0.05(13) . . . . ?
C34 C33 C38 C37 -0.82(13) . . . . ?
C34 C35 C36 C37 -0.04(13) . . . . ?
C34 C35 C36 C45 -179.97(7) . . . . ?
C35 C36 C37 C38 -0.30(13) . . . . ?
C36 C37 C38 C33 0.72(14) . . . . ?
C38 C33 C34 C35 0.49(13) . . . . ?
C39 C40 C41 C42 0.36(14) . . . . ?
C40 C39 C44 C43 0.69(13) . . . . ?
C40 C41 C42 O3 -177.40(10) . . . . ?
C40 C41 C42 O4 178.62(11) . . . . ?
C40 C41 C42 C43 0.95(15) . . . . ?
C41 C42 C43 C44 -1.43(15) . . . . ?
C42 O3 C46 C47 178.86(14) . . . . ?
C42 O4 C50 C48 173.20(15) . . . . ?
C42 C43 C44 C39 0.61(14) . . . . ?
C44 C39 C40 C41 -1.18(14) . . . . ?
C45 C36 C37 C38 179.63(8) . . . . ?

_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_AZN-7
_database_code_depnum_ccdc_archive 'CCDC 2457152'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Azonitrile
_chemical_name_systematic        
(E)-4-((4-heptyloxyphenyl)diazenyl)benzonitrile
_chemical_formula_moiety         'C20 H23 N3 O'
_chemical_formula_sum            'C20 H23 N3 O'
_chemical_formula_weight         321.41
_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 0.0020 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 0.0039 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0075 0.0059 '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                   5.8180(12)
_cell_length_b                   7.4410(15)
_cell_length_c                   40.745(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.78(3)
_cell_angle_gamma                90
_cell_volume                     1761.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      1.0
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      1.21
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Plate shaped'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            31293
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.618
_diffrn_reflns_theta_min         0.986
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4411
_reflns_number_total             5112
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0162(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+1.1659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 O1(N2,N3,N1,C3,C8,C6,C9,C4,C2,C12,C5,C13,C7,C10,C11,C1,C14,C18,C17,C16,C15,
 C19,C20)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,
 H15B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C4(H4), C12(H12), C13(H13), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.11313(5) 0.48114(5) 0.38796(2) 0.0216(2) Uani 1 1 d G . . . .
N2 N 0.46854(5) 0.26503(4) 0.51397(2) 0.0170(2) Uani 1 1 d G . . . .
N3 N 0.52171(4) 0.24015(4) 0.48451(2) 0.0170(2) Uani 1 1 d G . . . .
N1 N 1.25614(7) -0.01882(7) 0.63082(2) 0.0288(3) Uani 1 1 d G . . . .
C3 C 1.00724(6) 0.07102(7) 0.55326(2) 0.0180(2) Uani 1 1 d G . . . .
H3 H 1.149983 0.020502 0.547615 0.022 Uiso 1 1 calc R U . . .
C8 C 0.35351(4) 0.30090(3) 0.46059(2) 0.0160(2) Uani 1 1 d G . . . .
C6 C 0.59048(6) 0.22285(6) 0.57054(2) 0.0180(2) Uani 1 1 d G . . . .
H6 H 0.449173 0.276109 0.576108 0.022 Uiso 1 1 calc R U . . .
C9 C 0.40782(5) 0.28148(5) 0.42801(2) 0.0178(2) Uani 1 1 d G . . . .
H9 H 0.549797 0.227493 0.422964 0.021 Uiso 1 1 calc R U . . .
C4 C 0.84897(5) 0.12682(6) 0.52893(2) 0.0173(2) Uani 1 1 d G . . . .
H4 H 0.881455 0.113180 0.506442 0.021 Uiso 1 1 calc R U . . .
C2 C 0.95507(6) 0.08970(5) 0.58633(2) 0.0181(2) Uani 1 1 d G . . . .
C12 C -0.00880(6) 0.43584(6) 0.44364(2) 0.0176(2) Uani 1 1 d G . . . .
H12 H -0.151739 0.487441 0.448913 0.021 Uiso 1 1 calc R U . . .
C5 C 0.64145(5) 0.20321(4) 0.53758(2) 0.0163(2) Uani 1 1 d G . . . .
C13 C 0.14371(5) 0.37825(6) 0.46845(2) 0.0168(2) Uani 1 1 d G . . . .
H13 H 0.106494 0.391038 0.490776 0.020 Uiso 1 1 calc R U . . .
C7 C 0.74582(6) 0.16473(6) 0.59510(2) 0.0192(2) Uani 1 1 d G . . . .
H7 H 0.711065 0.175559 0.617557 0.023 Uiso 1 1 calc R U . . .
C10 C 0.25836(5) 0.33954(5) 0.40273(2) 0.0190(2) Uani 1 1 d G . . . .
H10 H 0.297016 0.326751 0.380466 0.023 Uiso 1 1 calc R U . . .
C11 C 0.04655(5) 0.41843(4) 0.41073(2) 0.0178(2) Uani 1 1 d G . . . .
C1 C 1.12214(7) 0.03055(6) 0.61147(2) 0.0210(2) Uani 1 1 d G . . . .
C14 C -0.07143(5) 0.45811(5) 0.35404(2) 0.0224(2) Uani 1 1 d G . . . .
H14A H -0.045710 0.329503 0.349191 0.027 Uiso 1 1 calc R U . . .
H14B H 0.067158 0.526381 0.348352 0.027 Uiso 1 1 calc R U . . .
C18 C -0.48668(8) 0.48896(8) 0.24189(2) 0.0256(3) Uani 1 1 d G . . . .
H18A H -0.483369 0.355975 0.241336 0.031 Uiso 1 1 calc R U . . .
H18B H -0.348327 0.533117 0.231190 0.031 Uiso 1 1 calc R U . . .
C17 C -0.47610(7) 0.55074(7) 0.27752(2) 0.0257(3) Uani 1 1 d G . . . .
H17A H -0.472926 0.683741 0.277982 0.031 Uiso 1 1 calc R U . . .
H17B H -0.618269 0.511447 0.287838 0.031 Uiso 1 1 calc R U . . .
C16 C -0.26974(6) 0.48047(6) 0.29794(2) 0.0255(3) Uani 1 1 d G . . . .
H16A H -0.127519 0.532090 0.289438 0.031 Uiso 1 1 calc R U . . .
H16B H -0.261728 0.348281 0.295489 0.031 Uiso 1 1 calc R U . . .
C15 C -0.28030(6) 0.52661(5) 0.33425(2) 0.0253(3) Uani 1 1 d G . . . .
H15A H -0.290461 0.658665 0.336762 0.030 Uiso 1 1 calc R U . . .
H15B H -0.420803 0.473102 0.342937 0.030 Uiso 1 1 calc R U . . .
C19 C -0.70094(8) 0.55460(8) 0.22229(2) 0.0307(3) Uani 1 1 d G . . . .
H19A H -0.839339 0.514464 0.233457 0.037 Uiso 1 1 calc R U . . .
H19B H -0.701121 0.687641 0.222089 0.037 Uiso 1 1 calc R U . . .
C20 C -0.71543(11) 0.48664(9) 0.18704(2) 0.0383(4) Uani 1 1 d G . . . .
H20A H -0.855988 0.532617 0.175765 0.057 Uiso 1 1 calc R U . . .
H20B H -0.718618 0.354959 0.187022 0.057 Uiso 1 1 calc R U . . .
H20C H -0.581019 0.528555 0.175628 0.057 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 C11 1.3630 . ?
O1 C14 1.4251 . ?
N2 N3 1.2676 . ?
N2 C5 1.4335 . ?
N3 C8 1.4210 . ?
N1 C1 1.1422 . ?
C3 H3 0.9500 . ?
C3 C4 1.3836 . ?
C3 C2 1.4024 . ?
C8 C9 1.3870 . ?
C8 C13 1.4006 . ?
C6 H6 0.9500 . ?
C6 C5 1.3970 . ?
C6 C7 1.3847 . ?
C9 H9 0.9500 . ?
C9 C10 1.3845 . ?
C4 H4 0.9500 . ?
C4 C5 1.3951 . ?
C2 C7 1.4013 . ?
C2 C1 1.4461 . ?
C12 H12 0.9500 . ?
C12 C13 1.3805 . ?
C12 C11 1.4002 . ?
C13 H13 0.9500 . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.4172 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5138 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.5212 . ?
C18 C19 1.5276 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.5199 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.5229 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5212 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C11 O1 C14 118.5 . . ?
N3 N2 C5 113.1 . . ?
N2 N3 C8 114.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4 . . ?
C2 C3 H3 120.3 . . ?
C9 C8 N3 116.2 . . ?
C9 C8 C13 120.2 . . ?
C13 C8 N3 123.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0 . . ?
C10 C9 H9 119.5 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7 . . ?
C5 C4 H4 120.2 . . ?
C3 C2 C1 118.8 . . ?
C7 C2 C3 121.0 . . ?
C7 C2 C1 120.2 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.2 . . ?
C11 C12 H12 119.9 . . ?
C6 C5 N2 115.9 . . ?
C4 C5 N2 123.3 . . ?
C4 C5 C6 120.8 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.8 . . ?
C12 C13 H13 120.1 . . ?
C6 C7 C2 119.0 . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7 . . ?
C11 C10 H10 120.7 . . ?
O1 C11 C12 116.1 . . ?
O1 C11 C10 123.8 . . ?
C12 C11 C10 120.1 . . ?
N1 C1 C2 178.4 . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
O1 C14 C15 107.8 . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H18A C18 H18B 107.7 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C17 C18 C19 113.4 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C16 C17 C18 114.4 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C17 C16 C15 112.7 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C14 C15 C16 111.9 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 113.2 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C14 C15 C16 -170.8 . . . . ?
N2 N3 C8 C9 178.0 . . . . ?
N2 N3 C8 C13 -1.4 . . . . ?
N3 N2 C5 C6 -178.5 . . . . ?
N3 N2 C5 C4 1.2 . . . . ?
N3 C8 C9 C10 -178.7 . . . . ?
N3 C8 C13 C12 179.2 . . . . ?
C3 C4 C5 N2 179.8 . . . . ?
C3 C4 C5 C6 -0.5 . . . . ?
C3 C2 C7 C6 -0.8 . . . . ?
C8 C9 C10 C11 -0.5 . . . . ?
C9 C8 C13 C12 -0.2 . . . . ?
C9 C10 C11 O1 179.7 . . . . ?
C9 C10 C11 C12 -0.3 . . . . ?
C4 C3 C2 C7 -0.3 . . . . ?
C4 C3 C2 C1 179.9 . . . . ?
C2 C3 C4 C5 0.9 . . . . ?
C5 N2 N3 C8 -179.8 . . . . ?
C5 C6 C7 C2 1.2 . . . . ?
C13 C8 C9 C10 0.8 . . . . ?
C13 C12 C11 O1 -179.2 . . . . ?
C13 C12 C11 C10 0.8 . . . . ?
C7 C6 C5 N2 179.1 . . . . ?
C7 C6 C5 C4 -0.6 . . . . ?
C11 O1 C14 C15 176.0 . . . . ?
C11 C12 C13 C8 -0.5 . . . . ?
C1 C2 C7 C6 179.0 . . . . ?
C14 O1 C11 C12 -176.7 . . . . ?
C14 O1 C11 C10 3.4 . . . . ?
C18 C17 C16 C15 -173.1 . . . . ?
C17 C18 C19 C20 -177.8 . . . . ?
C17 C16 C15 C14 -179.1 . . . . ?
C19 C18 C17 C16 177.5 . . . . ?

_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_AZN-6
_database_code_depnum_ccdc_archive 'CCDC 2457151'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Azonitrile
_chemical_name_common            
(E)-4-((4-hexyloxyphenyl)diazenyl)benzonitrile
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N3 O'
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39

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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   5.8120(12)
_cell_length_b                   7.4680(15)
_cell_length_c                   37.455(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.01(3)
_cell_angle_gamma                90
_cell_volume                     1623.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.1
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      1.26
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            23970
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         27.811
_diffrn_reflns_theta_min         2.145
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3803
_reflns_number_total             3981
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.153(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²+0.3428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 O1(N2,N3,N1,C7,C4,C13,C10,C12,C9,C6,C3,C1,C5,C8,C11,C2,C16,C18,C14,C15,C17,C19)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C10(H10), C12(H12), C9(H9), C6(H6), C3(H3)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.63411(4) 0.48555(4) 0.61964(2) 0.02073(17) Uani 1 1 d G . . . .
N2 N 0.03279(3) 0.26614(3) 0.48533(2) 0.01784(18) Uani 1 1 d G . . . .
N3 N -0.01580(3) 0.23887(3) 0.51742(2) 0.01752(18) Uani 1 1 d G . . . .
N1 N -0.75241(5) -0.01576(5) 0.35731(2) 0.0282(2) Uani 1 1 d G . . . .
C7 C -0.50328(5) 0.07110(5) 0.44215(2) 0.01832(19) Uani 1 1 d G . . . .
H7 H -0.644700 0.017883 0.448104 0.022 Uiso 1 1 calc R U . . .
C4 C -0.08833(5) 0.22686(5) 0.42383(2) 0.01849(19) Uani 1 1 d G . . . .
H4 H 0.052602 0.280994 0.417911 0.022 Uiso 1 1 calc R U . . .
C13 C 0.10654(4) 0.28267(4) 0.57880(2) 0.01791(19) Uani 1 1 d G . . . .
H13 H -0.033965 0.228891 0.585024 0.021 Uiso 1 1 calc R U . . .
C10 C 0.51918(4) 0.43606(5) 0.55986(2) 0.01793(19) Uani 1 1 d G . . . .
H10 H 0.660772 0.487543 0.553492 0.022 Uiso 1 1 calc R U . . .
C12 C 0.26331(4) 0.34143(4) 0.60559(2) 0.01834(19) Uani 1 1 d G . . . .
H12 H 0.230350 0.328585 0.630032 0.022 Uiso 1 1 calc R U . . .
C9 C 0.36308(4) 0.37788(4) 0.53371(2) 0.01720(19) Uani 1 1 d G . . . .
H9 H 0.396861 0.389027 0.509265 0.021 Uiso 1 1 calc R U . . .
C6 C -0.34751(4) 0.12656(4) 0.46866(2) 0.01774(19) Uani 1 1 d G . . . .
H6 H -0.381440 0.112852 0.493044 0.021 Uiso 1 1 calc R U . . .
C3 C -0.24513(5) 0.17081(5) 0.39694(2) 0.01917(19) Uani 1 1 d G . . . .
H3 H -0.211779 0.184913 0.372538 0.023 Uiso 1 1 calc R U . . .
C1 C -0.61758(5) 0.03377(4) 0.37862(2) 0.0209(2) Uani 1 1 d G . . . .
C5 C -0.13803(4) 0.20355(3) 0.45969(2) 0.01657(19) Uani 1 1 d G . . . .
C8 C 0.15363(3) 0.30194(2) 0.54292(2) 0.01633(19) Uani 1 1 d G . . . .
C11 C 0.47031(3) 0.41975(3) 0.59611(2) 0.01746(19) Uani 1 1 d G . . . .
C2 C -0.45256(4) 0.09342(4) 0.40614(2) 0.01815(19) Uani 1 1 d G . . . .
C16 C 0.81467(5) 0.49709(5) 0.71702(2) 0.0223(2) Uani 1 1 d G . . . .
H16A H 0.675003 0.550159 0.726757 0.027 Uiso 1 1 calc R U . . .
H16B H 0.807534 0.365902 0.720596 0.027 Uiso 1 1 calc R U . . .
C18 C 1.04398(6) 0.51285(6) 0.77666(2) 0.0247(2) Uani 1 1 d G . . . .
H18A H 0.905378 0.554599 0.788495 0.030 Uiso 1 1 calc R U . . .
H18B H 1.046587 0.380430 0.777852 0.030 Uiso 1 1 calc R U . . .
C14 C 0.60210(4) 0.46440(4) 0.65718(2) 0.0213(2) Uani 1 1 d G . . . .
H14A H 0.580459 0.336357 0.662970 0.026 Uiso 1 1 calc R U . . .
H14B H 0.464039 0.531306 0.663992 0.026 Uiso 1 1 calc R U . . .
C15 C 0.81421(4) 0.53627(4) 0.67717(2) 0.0229(2) Uani 1 1 d G . . . .
H15A H 0.822541 0.667357 0.673518 0.027 Uiso 1 1 calc R U . . .
H15B H 0.952664 0.481954 0.667293 0.027 Uiso 1 1 calc R U . . .
C17 C 1.02615(5) 0.57024(5) 0.73769(2) 0.0226(2) Uani 1 1 d G . . . .
H17A H 1.022607 0.702662 0.736561 0.027 Uiso 1 1 calc R U . . .
H17B H 1.165653 0.529467 0.725969 0.027 Uiso 1 1 calc R U . . .
C19 C 1.25665(6) 0.58556(6) 0.79685(2) 0.0298(2) Uani 1 1 d G . . . .
H19A H 1.394835 0.537704 0.786353 0.045 Uiso 1 1 calc R U . . .
H19B H 1.255259 0.549455 0.821991 0.045 Uiso 1 1 calc R U . . .
H19C H 1.257381 0.716540 0.795257 0.045 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 C11 1.3552 . ?
O1 C14 1.4367 . ?
N2 N3 1.2655 . ?
N2 C5 1.4235 . ?
N3 C8 1.4160 . ?
N1 C1 1.1499 . ?
C7 H7 0.9500 . ?
C7 C6 1.3722 . ?
C7 C2 1.4055 . ?
C4 H4 0.9500 . ?
C4 C3 1.3870 . ?
C4 C5 1.3994 . ?
C13 H13 0.9500 . ?
C13 C12 1.3906 . ?
C13 C8 1.3929 . ?
C10 H10 0.9500 . ?
C10 C9 1.3704 . ?
C10 C11 1.4069 . ?
C12 H12 0.9500 . ?
C12 C11 1.4001 . ?
C9 H9 0.9500 . ?
C9 C8 1.4023 . ?
C6 H6 0.9500 . ?
C6 C5 1.4031 . ?
C3 H3 0.9500 . ?
C3 C2 1.3963 . ?
C1 C2 1.4412 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.5209 . ?
C16 C17 1.5195 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.5196 . ?
C18 C19 1.5154 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5072 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C11 O1 C14 118.3 . . ?
N3 N2 C5 113.9 . . ?
N2 N3 C8 113.9 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C2 119.7 . . ?
C2 C7 H7 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9 . . ?
C5 C4 H4 120.0 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C8 120.6 . . ?
C8 C13 H13 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2 . . ?
C11 C10 H10 119.9 . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.2 . . ?
C11 C12 H12 120.4 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.3 . . ?
C2 C3 H3 120.4 . . ?
N1 C1 C2 178.3 . . ?
C4 C5 N2 115.8 . . ?
C4 C5 C6 120.4 . . ?
C6 C5 N2 123.8 . . ?
C13 C8 N3 116.8 . . ?
C13 C8 C9 119.7 . . ?
C9 C8 N3 123.4 . . ?
O1 C11 C10 115.2 . . ?
O1 C11 C12 124.8 . . ?
C12 C11 C10 120.0 . . ?
C7 C2 C1 119.0 . . ?
C3 C2 C7 120.9 . . ?
C3 C2 C1 120.1 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C17 C16 C15 113.0 . . ?
H18A C18 H18B 107.8 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C19 C18 C17 113.0 . . ?
O1 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
O1 C14 C15 107.6 . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 C16 112.2 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C17 C18 113.6 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C14 C15 C16 -171.9 . . . . ?
N2 N3 C8 C13 177.5 . . . . ?
N2 N3 C8 C9 -3.7 . . . . ?
N3 N2 C5 C4 -178.4 . . . . ?
N3 N2 C5 C6 3.1 . . . . ?
C7 C6 C5 N2 179.5 . . . . ?
C7 C6 C5 C4 1.0 . . . . ?
C4 C3 C2 C7 -0.3 . . . . ?
C4 C3 C2 C1 -179.8 . . . . ?
C13 C12 C11 O1 178.5 . . . . ?
C13 C12 C11 C10 -0.9 . . . . ?
C10 C9 C8 N3 -180.0 . . . . ?
C10 C9 C8 C13 -1.2 . . . . ?
C12 C13 C8 N3 -179.8 . . . . ?
C12 C13 C8 C9 1.3 . . . . ?
C9 C10 C11 O1 -178.4 . . . . ?
C9 C10 C11 C12 1.0 . . . . ?
C6 C7 C2 C3 0.2 . . . . ?
C6 C7 C2 C1 179.7 . . . . ?
C3 C4 C5 N2 -179.7 . . . . ?
C3 C4 C5 C6 -1.1 . . . . ?
C5 N2 N3 C8 -179.7 . . . . ?
C5 C4 C3 C2 0.7 . . . . ?
C8 C13 C12 C11 -0.3 . . . . ?
C11 O1 C14 C15 176.0 . . . . ?
C11 C10 C9 C8 0.1 . . . . ?
C2 C7 C6 C5 -0.6 . . . . ?
C14 O1 C11 C10 -176.5 . . . . ?
C14 O1 C11 C12 4.1 . . . . ?
C15 C16 C17 C18 -172.9 . . . . ?
C17 C16 C15 C14 -179.4 . . . . ?
C19 C18 C17 C16 179.5 . . . . ?

_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_AZN-11
_database_code_depnum_ccdc_archive 'CCDC 2457155'
loop_
_audit_author_name
_audit_author_address
'Susanta Nayak'
;Visvesvaraya National Institute of Technology
India
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

#===============================================================================
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Azonitrile
_chemical_name_systematic        
(E)-4-((4-undecyloxyphenyl)diazenyl)benzonitrile
_chemical_formula_moiety         'C24 H31 N3 O'
_chemical_formula_sum            'C24 H31 N3 O'
_chemical_formula_weight         377.52
_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 0.0020 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 0.0039 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0075 0.0059 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8110(12)
_cell_length_b                   7.3670(15)
_cell_length_c                   49.550(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.10(3)
_cell_angle_gamma                90
_cell_volume                     2118.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6192
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      1.6
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      1.18
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       69
_diffrn_reflns_limit_l_min       -69
_diffrn_reflns_number            35746
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         1.621
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5279
_reflns_number_total             6192
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0063(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         6192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.047
_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)+(0.0843P)²+1.4827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 O1(N2,N3,N1,C5,C6,C8,C4,C2,C13,C3,C11,C12,C9,C7,C10,C1,C14,C18,C22,C19,C21,
 C20,C17,C16,C15,C23,C24)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C22(H22A,H22B), C19(H19A,H19B), C21(H21A,
 H21B), C20(H20A,H20B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B),
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C13(H13), C3(H3), C12(H12), C9(H9), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.61639(5) 0.51816(4) 0.59262(2) 0.0206(2) Uani 1 1 d G . . . .
N2 N 0.03136(5) 0.73530(4) 0.48889(2) 0.0162(2) Uani 1 1 d G . . . .
N3 N -0.02058(4) 0.75843(4) 0.51293(2) 0.0163(2) Uani 1 1 d G . . . .
N1 N -0.76109(7) 1.01973(7) 0.39241(2) 0.0273(3) Uani 1 1 d G . . . .
C5 C -0.13969(5) 0.79696(4) 0.46944(2) 0.0152(2) Uani 1 1 d G . . . .
C6 C -0.08801(6) 0.77852(6) 0.44226(2) 0.0170(2) Uani 1 1 d G . . . .
H6 H 0.055407 0.728146 0.437745 0.020 Uiso 1 1 calc R U . . .
C8 C 0.14620(4) 0.69780(3) 0.53263(2) 0.0153(2) Uani 1 1 d G . . . .
C4 C -0.34959(5) 0.87348(6) 0.47632(2) 0.0161(2) Uani 1 1 d G . . . .
H4 H -0.382294 0.887331 0.494786 0.019 Uiso 1 1 calc R U . . .
C2 C -0.45651(6) 0.90999(5) 0.42914(2) 0.0168(2) Uani 1 1 d G . . . .
C13 C 0.35856(5) 0.62049(5) 0.52648(2) 0.0158(2) Uani 1 1 d G . . . .
H13 H 0.395803 0.607214 0.508151 0.019 Uiso 1 1 calc R U . . .
C3 C -0.50844(6) 0.92860(7) 0.45634(2) 0.0172(2) Uani 1 1 d G . . . .
H3 H -0.651785 0.978738 0.460929 0.021 Uiso 1 1 calc R U . . .
C11 C 0.45634(5) 0.58229(4) 0.57401(2) 0.0169(2) Uani 1 1 d G . . . .
C12 C 0.51244(6) 0.56406(6) 0.54680(2) 0.0169(2) Uani 1 1 d G . . . .
H12 H 0.656105 0.512945 0.542536 0.020 Uiso 1 1 calc R U . . .
C9 C 0.09212(4) 0.71764(5) 0.55962(2) 0.0171(2) Uani 1 1 d G . . . .
H9 H -0.050986 0.770309 0.563755 0.021 Uiso 1 1 calc R U . . .
C7 C -0.24685(6) 0.83402(6) 0.42191(2) 0.0180(2) Uani 1 1 d G . . . .
H7 H -0.214085 0.820765 0.403437 0.022 Uiso 1 1 calc R U . . .
C10 C 0.24479(4) 0.66139(4) 0.58044(2) 0.0179(2) Uani 1 1 d G . . . .
H10 H 0.207608 0.675858 0.598751 0.021 Uiso 1 1 calc R U . . .
C1 C -0.62366(7) 0.97002(6) 0.40849(2) 0.0199(2) Uani 1 1 d G . . . .
C14 C 0.57472(5) 0.53974(4) 0.62047(2) 0.0215(3) Uani 1 1 d G . . . .
H14A H 0.436445 0.469856 0.624983 0.026 Uiso 1 1 calc R U . . .
H14B H 0.547855 0.669303 0.624570 0.026 Uiso 1 1 calc R U . . .
C18 C 0.99245(6) 0.50673(6) 0.71292(2) 0.0229(3) Uani 1 1 d G . . . .
H18A H 0.851884 0.465507 0.721551 0.027 Uiso 1 1 calc R U . . .
H18B H 0.994018 0.641083 0.713313 0.027 Uiso 1 1 calc R U . . .
C22 C 1.47046(9) 0.51043(8) 0.80283(2) 0.0231(3) Uani 1 1 d G . . . .
H22A H 1.476659 0.644629 0.802113 0.028 Uiso 1 1 calc R U . . .
H22B H 1.334601 0.476048 0.812921 0.028 Uiso 1 1 calc R U . . .
C19 C 1.20334(6) 0.43608(6) 0.72923(2) 0.0227(3) Uani 1 1 d G . . . .
H19A H 1.343165 0.470642 0.719887 0.027 Uiso 1 1 calc R U . . .
H19B H 1.196432 0.301851 0.729693 0.027 Uiso 1 1 calc R U . . .
C21 C 1.44005(7) 0.43638(7) 0.77401(2) 0.0230(3) Uani 1 1 d G . . . .
H21A H 1.577643 0.468860 0.764102 0.028 Uiso 1 1 calc R U . . .
H21B H 1.431930 0.302276 0.774826 0.028 Uiso 1 1 calc R U . . .
C20 C 1.22583(7) 0.50685(7) 0.75818(2) 0.0227(3) Uani 1 1 d G . . . .
H20A H 1.087482 0.470643 0.767683 0.027 Uiso 1 1 calc R U . . .
H20B H 1.231073 0.641140 0.757798 0.027 Uiso 1 1 calc R U . . .
C17 C 0.98159(6) 0.44348(5) 0.68368(2) 0.0231(3) Uani 1 1 d G . . . .
H17A H 0.976314 0.309177 0.683343 0.028 Uiso 1 1 calc R U . . .
H17B H 1.124400 0.481772 0.675255 0.028 Uiso 1 1 calc R U . . .
C16 C 0.77517(5) 0.51667(5) 0.66687(2) 0.0236(3) Uani 1 1 d G . . . .
H16A H 0.768859 0.650167 0.669001 0.028 Uiso 1 1 calc R U . . .
H16B H 0.632307 0.465354 0.673781 0.028 Uiso 1 1 calc R U . . .
C15 C 0.78437(6) 0.47092(4) 0.63688(2) 0.0245(3) Uani 1 1 d G . . . .
H15A H 0.924706 0.525399 0.629802 0.029 Uiso 1 1 calc R U . . .
H15B H 0.795047 0.337614 0.634755 0.029 Uiso 1 1 calc R U . . .
C23 C 1.68606(9) 0.44087(8) 0.81793(2) 0.0286(3) Uani 1 1 d G . . . .
H23A H 1.821771 0.474574 0.807769 0.034 Uiso 1 1 calc R U . . .
H23B H 1.679359 0.306710 0.818730 0.034 Uiso 1 1 calc R U . . .
C24 C 1.71804(11) 0.51596(9) 0.84688(2) 0.0347(4) Uani 1 1 d G . . . .
H24A H 1.728280 0.648660 0.846252 0.052 Uiso 1 1 calc R U . . .
H24B H 1.859962 0.466564 0.855593 0.052 Uiso 1 1 calc R U . . .
H24C H 1.586238 0.480466 0.857229 0.052 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 C11 1.3586 . ?
O1 C14 1.4228 . ?
N2 N3 1.2562 . ?
N2 C5 1.4211 . ?
N3 C8 1.4104 . ?
N1 C1 1.1566 . ?
C5 C6 1.4022 . ?
C5 C4 1.4024 . ?
C6 H6 0.9500 . ?
C6 C7 1.3911 . ?
C8 C13 1.4074 . ?
C8 C9 1.3979 . ?
C4 H4 0.9500 . ?
C4 C3 1.3777 . ?
C2 C3 1.4037 . ?
C2 C7 1.4047 . ?
C2 C1 1.4417 . ?
C13 H13 0.9500 . ?
C13 C12 1.3743 . ?
C3 H3 0.9500 . ?
C11 C12 1.4106 . ?
C11 C10 1.4123 . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.3871 . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5150 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5227 . ?
C18 C17 1.5200 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.5300 . ?
C22 C23 1.5135 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5252 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.5260 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.5216 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.5275 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5393 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C11 O1 C14 118.2 . . ?
N3 N2 C5 113.9 . . ?
N2 N3 C8 115.0 . . ?
C6 C5 N2 116.2 . . ?
C6 C5 C4 120.4 . . ?
C4 C5 N2 123.3 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C13 C8 N3 123.8 . . ?
C9 C8 N3 116.6 . . ?
C9 C8 C13 119.6 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C2 C7 121.2 . . ?
C3 C2 C1 118.7 . . ?
C7 C2 C1 120.1 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5 . . ?
C12 C13 H13 119.8 . . ?
C4 C3 C2 119.4 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O1 C11 C12 115.5 . . ?
O1 C11 C10 124.2 . . ?
C12 C11 C10 120.3 . . ?
C13 C12 C11 119.8 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8 . . ?
C10 C9 H9 119.6 . . ?
C6 C7 C2 118.9 . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
C11 C10 H10 120.5 . . ?
C9 C10 C11 119.0 . . ?
C9 C10 H10 120.5 . . ?
N1 C1 C2 178.3 . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
O1 C14 C15 108.0 . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 113.1 . . ?
H22A C22 H22B 107.8 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C23 C22 C21 113.0 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C18 C19 C20 114.1 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C20 C21 C22 114.1 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C19 C20 C21 113.1 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C18 C17 C16 113.8 . . ?
H17A C17 H17B 107.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C17 C16 C15 112.7 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C14 C15 C16 112.3 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C22 C23 C24 113.2 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C11 C12 C13 178.2 . . . . ?
O1 C11 C10 C9 -178.3 . . . . ?
O1 C14 C15 C16 170.4 . . . . ?
N2 N3 C8 C13 1.4 . . . . ?
N2 N3 C8 C9 -178.6 . . . . ?
N2 C5 C6 C7 179.4 . . . . ?
N2 C5 C4 C3 -179.3 . . . . ?
N3 N2 C5 C6 178.5 . . . . ?
N3 N2 C5 C4 -1.2 . . . . ?
N3 C8 C13 C12 -179.8 . . . . ?
N3 C8 C9 C10 179.8 . . . . ?
C5 N2 N3 C8 179.8 . . . . ?
C5 C6 C7 C2 0.7 . . . . ?
C5 C4 C3 C2 -1.0 . . . . ?
C6 C5 C4 C3 1.0 . . . . ?
C8 C13 C12 C11 0.6 . . . . ?
C8 C9 C10 C11 -0.4 . . . . ?
C4 C5 C6 C7 -0.9 . . . . ?
C13 C8 C9 C10 -0.3 . . . . ?
C3 C2 C7 C6 -0.7 . . . . ?
C11 O1 C14 C15 -175.8 . . . . ?
C12 C11 C10 C9 1.1 . . . . ?
C9 C8 C13 C12 0.2 . . . . ?
C7 C2 C3 C4 0.8 . . . . ?
C10 C11 C12 C13 -1.2 . . . . ?
C1 C2 C3 C4 -179.4 . . . . ?
C1 C2 C7 C6 179.5 . . . . ?
C14 O1 C11 C12 177.3 . . . . ?
C14 O1 C11 C10 -3.3 . . . . ?
C18 C19 C20 C21 -179.2 . . . . ?
C18 C17 C16 C15 172.8 . . . . ?
C22 C21 C20 C19 178.1 . . . . ?
C19 C18 C17 C16 -178.5 . . . . ?
C21 C22 C23 C24 179.7 . . . . ?
C17 C18 C19 C20 176.5 . . . . ?
C17 C16 C15 C14 178.4 . . . . ?
C23 C22 C21 C20 -179.1 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
