# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2050357'
loop_
_audit_author_name
_audit_author_address
'Tamas Holczbauer'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-12-15 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'[(E)-2-(1-hexyl-1H-1,2,3-triazol-4-yl)-5-(phenyldiazenyl)pyridine]palladium dichloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 Cl2 N6 Pd'
_chemical_formula_sum            'C19 H22 Cl2 N6 Pd'
_chemical_formula_weight         511.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   12.8830(7)
_cell_length_b                   8.8827(4)
_cell_length_c                   9.6095(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.352(8)
_cell_angle_gamma                90
_cell_volume                     1031.02(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    46143
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.46

_exptl_crystal_description       platelet
_exptl_crystal_colour            redish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.177
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.772776
_exptl_absorpt_correction_T_max  0.960418
_exptl_absorpt_process_details   
;
T. Higashi,  September 1998 last update: Sep 1, 2011
T.Higashi, Numerical Absorption Correction, NUMABS, 2002
T.Higashi, Empirical Absorption Correction, 2001
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_radiation_detector       RX
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            41991
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.221
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4202
_reflns_number_gt                4187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
PLATON (Spek, 2009)
Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_publication_material  
;
PLATON (Spek, 2009)
Olex2 1.3 (Dolomanov et al., 2009)
# Spek, A. L. (2009). Acta Cryst. D65, 148--155
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+0.3979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     254
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0184
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0375
_refine_ls_wR_factor_gt          0.0374
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.50388(2) 0.39896(2) 0.46396(2) 0.01746(6) Uani 1 1 d . . . . .
Cl1 Cl 0.42497(7) 0.19072(10) 0.52520(10) 0.02749(19) Uani 1 1 d . . . . .
Cl2 Cl 0.62182(7) 0.25207(10) 0.39119(10) 0.02269(17) Uani 1 1 d . . . . .
N1 N 0.5645(3) 0.5946(3) 0.4210(3) 0.0202(6) Uani 1 1 d . . . . .
N2 N 0.6339(2) 0.6342(3) 0.3576(3) 0.0219(6) Uani 1 1 d . . . . .
N3 N 0.6403(3) 0.7852(3) 0.3669(4) 0.0211(7) Uani 1 1 d . . . . .
N7 N 0.4084(2) 0.5466(4) 0.5314(3) 0.0208(6) Uani 1 1 d . . . . .
N18 N 0.1690(2) 0.5712(3) 0.6475(3) 0.0250(6) Uani 1 1 d . . . . .
N19 N 0.1288(2) 0.6706(3) 0.7070(3) 0.0240(6) Uani 1 1 d . . . . .
C4 C 0.5744(3) 0.8411(4) 0.4355(4) 0.0213(7) Uani 1 1 d . . . . .
H4 H 0.564240 0.943871 0.455029 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5253(2) 0.7191(3) 0.4709(5) 0.0168(7) Uani 1 1 d . . . . .
C6 C 0.4404(2) 0.6920(4) 0.5363(4) 0.0190(6) Uani 1 1 d . . . . .
C8 C 0.3220(3) 0.5116(4) 0.5724(4) 0.0228(7) Uani 1 1 d . . . . .
H8 H 0.298179 0.409881 0.566889 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2667(3) 0.6210(4) 0.6229(4) 0.0236(7) Uani 1 1 d . . . . .
C10 C 0.3030(3) 0.7699(4) 0.6367(4) 0.0234(7) Uani 1 1 d . . . . .
H10 H 0.268329 0.844999 0.675721 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3907(3) 0.8047(5) 0.5920(5) 0.0235(9) Uani 1 1 d . . . . .
H11 H 0.417222 0.905266 0.599205 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7076(3) 0.8647(4) 0.2941(4) 0.0246(7) Uani 1 1 d . . . . .
H12A H 0.697903 0.974552 0.302414 0.030 Uiso 1 1 calc R U . . .
H12B H 0.680101 0.838679 0.187275 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8302(3) 0.8273(4) 0.3597(4) 0.0254(7) Uani 1 1 d . . . . .
H13A H 0.840025 0.717098 0.373211 0.030 Uiso 1 1 calc R U . . .
H13B H 0.863028 0.875878 0.458018 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8886(3) 0.8834(4) 0.2556(4) 0.0272(8) Uani 1 1 d . . . . .
H14A H 0.877376 0.993439 0.242594 0.033 Uiso 1 1 calc R U . . .
H14B H 0.853505 0.835801 0.157189 0.033 Uiso 1 1 calc R U . . .
C15 C 1.0129(3) 0.8507(4) 0.3097(4) 0.0266(7) Uani 1 1 d . . . . .
H15A H 1.050439 0.909739 0.400760 0.032 Uiso 1 1 calc R U . . .
H15B H 1.025611 0.742590 0.334997 0.032 Uiso 1 1 calc R U . . .
C16 C 1.0626(3) 0.8905(4) 0.1920(4) 0.0313(8) Uani 1 1 d . . . . .
H16A H 1.051811 0.999445 0.170094 0.038 Uiso 1 1 calc R U . . .
H16B H 1.021782 0.835200 0.099708 0.038 Uiso 1 1 calc R U . . .
C17 C 1.1854(3) 0.8543(5) 0.2359(5) 0.0398(9) Uani 1 1 d . . . . .
H17A H 1.209530 0.872821 0.151287 0.060 Uiso 1 1 calc R U . . .
H17B H 1.197954 0.748391 0.265444 0.060 Uiso 1 1 calc R U . . .
H17C H 1.227787 0.918541 0.319241 0.060 Uiso 1 1 calc R U . . .
C20 C 0.0233(3) 0.6324(4) 0.7151(4) 0.0221(7) Uani 1 1 d . . . . .
C21 C -0.0451(3) 0.5215(4) 0.6281(4) 0.0259(7) Uani 1 1 d . . . . .
H21 H -0.019843 0.459671 0.565749 0.031 Uiso 1 1 calc R U . . .
C22 C -0.1499(3) 0.5019(4) 0.6332(4) 0.0284(7) Uani 1 1 d . . . . .
H22 H -0.197225 0.427060 0.573106 0.034 Uiso 1 1 calc R U . . .
C23 C -0.1867(3) 0.5905(4) 0.7252(4) 0.0267(7) Uani 1 1 d . . . . .
H23 H -0.258619 0.575298 0.729214 0.032 Uiso 1 1 calc R U . . .
C24 C -0.1187(3) 0.7015(4) 0.8113(4) 0.0279(8) Uani 1 1 d . . . . .
H24 H -0.143984 0.762149 0.874489 0.034 Uiso 1 1 calc R U . . .
C25 C -0.0135(3) 0.7242(4) 0.8057(4) 0.0248(7) Uani 1 1 d . . . . .
H25 H 0.032697 0.801620 0.862985 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N1 2.006(3) . ?
Pd1 N7 2.050(3) . ?
Pd1 Cl1 2.2841(9) . ?
Pd1 Cl2 2.2889(9) . ?
N1 N2 1.294(5) . ?
N1 C5 1.370(5) . ?
N2 N3 1.345(4) . ?
N3 C4 1.338(5) . ?
N3 C12 1.471(5) . ?
N7 C8 1.341(4) . ?
N7 C6 1.352(5) . ?
N18 N19 1.257(4) . ?
N18 C9 1.428(4) . ?
N19 C20 1.430(4) . ?
C4 C5 1.357(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.458(4) . ?
C6 C11 1.392(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(5) . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.520(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.530(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C20 C21 1.390(5) . ?
C20 C25 1.391(5) . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pd1 N7 80.21(15) . . ?
N1 Pd1 Cl1 173.98(10) . . ?
N7 Pd1 Cl1 93.84(9) . . ?
N1 Pd1 Cl2 94.80(10) . . ?
N7 Pd1 Cl2 174.69(9) . . ?
Cl1 Pd1 Cl2 91.10(4) . . ?
N2 N1 C5 110.2(3) . . ?
N2 N1 Pd1 135.6(2) . . ?
C5 N1 Pd1 114.2(3) . . ?
N1 N2 N3 106.0(3) . . ?
C4 N3 N2 111.7(3) . . ?
C4 N3 C12 129.5(3) . . ?
N2 N3 C12 118.7(3) . . ?
C8 N7 C6 119.0(3) . . ?
C8 N7 Pd1 126.5(3) . . ?
C6 N7 Pd1 114.4(2) . . ?
N19 N18 C9 112.6(3) . . ?
N18 N19 C20 114.1(3) . . ?
N3 C4 C5 105.0(3) . . ?
N3 C4 H4 127.5 . . ?
C5 C4 H4 127.5 . . ?
C4 C5 N1 107.2(3) . . ?
C4 C5 C6 136.5(3) . . ?
N1 C5 C6 116.1(3) . . ?
N7 C6 C11 121.7(3) . . ?
N7 C6 C5 114.1(3) . . ?
C11 C6 C5 124.2(3) . . ?
N7 C8 C9 121.4(3) . . ?
N7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 N18 115.5(3) . . ?
C10 C9 N18 124.3(3) . . ?
C11 C10 C9 118.0(3) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C11 C6 119.7(4) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
N3 C12 C13 113.4(3) . . ?
N3 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 109.6(3) . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 114.3(3) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 111.4(3) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 114.2(3) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C20 C25 120.6(3) . . ?
C21 C20 N19 123.5(3) . . ?
C25 C20 N19 115.6(3) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C20 C25 H25 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 0.3(4) . . . . ?
Pd1 N1 N2 N3 -179.0(3) . . . . ?
N1 N2 N3 C4 -0.4(4) . . . . ?
N1 N2 N3 C12 -175.7(3) . . . . ?
C9 N18 N19 C20 172.0(3) . . . . ?
N2 N3 C4 C5 0.3(4) . . . . ?
C12 N3 C4 C5 174.9(4) . . . . ?
N3 C4 C5 N1 -0.1(4) . . . . ?
N3 C4 C5 C6 -175.1(4) . . . . ?
N2 N1 C5 C4 -0.2(4) . . . . ?
Pd1 N1 C5 C4 179.3(2) . . . . ?
N2 N1 C5 C6 176.0(3) . . . . ?
Pd1 N1 C5 C6 -4.5(4) . . . . ?
C8 N7 C6 C11 4.3(5) . . . . ?
Pd1 N7 C6 C11 -174.3(3) . . . . ?
C8 N7 C6 C5 -172.3(3) . . . . ?
Pd1 N7 C6 C5 9.1(4) . . . . ?
C4 C5 C6 N7 171.6(4) . . . . ?
N1 C5 C6 N7 -3.2(4) . . . . ?
C4 C5 C6 C11 -5.0(6) . . . . ?
N1 C5 C6 C11 -179.7(3) . . . . ?
C6 N7 C8 C9 -1.5(5) . . . . ?
Pd1 N7 C8 C9 176.9(3) . . . . ?
N7 C8 C9 C10 -2.3(5) . . . . ?
N7 C8 C9 N18 173.4(3) . . . . ?
N19 N18 C9 C8 173.3(3) . . . . ?
N19 N18 C9 C10 -11.2(5) . . . . ?
C8 C9 C10 C11 3.2(5) . . . . ?
N18 C9 C10 C11 -172.1(3) . . . . ?
C9 C10 C11 C6 -0.5(5) . . . . ?
N7 C6 C11 C10 -3.3(5) . . . . ?
C5 C6 C11 C10 172.9(3) . . . . ?
C4 N3 C12 C13 121.5(4) . . . . ?
N2 N3 C12 C13 -64.2(4) . . . . ?
N3 C12 C13 C14 166.4(3) . . . . ?
C12 C13 C14 C15 -179.5(3) . . . . ?
C13 C14 C15 C16 172.4(3) . . . . ?
C14 C15 C16 C17 -177.5(3) . . . . ?
N18 N19 C20 C21 -18.8(5) . . . . ?
N18 N19 C20 C25 167.6(3) . . . . ?
C25 C20 C21 C22 -0.6(5) . . . . ?
N19 C20 C21 C22 -173.9(3) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C23 C24 C25 C20 -1.4(5) . . . . ?
C21 C20 C25 C24 1.6(5) . . . . ?
N19 C20 C25 C24 175.4(3) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2050358'
loop_
_audit_author_name
_audit_author_address
'Tamas Holczbauer'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2020-12-15 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(E)-2-(1-benzyl-1H-1,2,3-triazol-4-yl)-5-(phenyldiazenyl)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N6'
_chemical_formula_sum            'C20 H16 N6'
_chemical_formula_weight         340.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8998(2)
_cell_length_b                   9.3629(3)
_cell_length_c                   15.9508(6)
_cell_angle_alpha                73.354(5)
_cell_angle_beta                 81.870(6)
_cell_angle_gamma                81.835(6)
_cell_volume                     830.90(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    16531
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      68.31

_exptl_crystal_description       chunk
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.834433
_exptl_absorpt_correction_T_max  0.947750
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
 NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_radiation_detector       RX
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            17869
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.959
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2979
_reflns_number_gt                2720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;

_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;

_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;

_computing_structure_solution    
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;

_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2018)
;

_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.

Olex2 1.3 (Dolomanov et al., 2009)
;

_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008

Olex2 1.3 (Dolomanov et al., 2009)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0494(2) 0.77247(15) 0.05995(9) 0.0359(3) Uani 1 1 d . . . . .
N8 N 0.1160(2) 1.01121(16) 0.18152(9) 0.0396(3) Uani 1 1 d . . . . .
N9 N -0.0220(2) 1.07376(16) 0.23652(9) 0.0412(4) Uani 1 1 d . . . . .
N10 N -0.2348(2) 1.03650(14) 0.23751(8) 0.0341(3) Uani 1 1 d . . . . .
N19 N 0.3350(2) 0.61154(14) -0.09800(8) 0.0354(3) Uani 1 1 d . . . . .
N20 N 0.5432(2) 0.61482(15) -0.12821(9) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.0921(3) 0.85018(16) 0.08410(9) 0.0312(3) Uani 1 1 d . . . . .
C3 C 0.3228(3) 0.85506(19) 0.05043(10) 0.0362(4) Uani 1 1 d . . . . .
H3 H 0.417343 0.911381 0.069335 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4127(3) 0.77807(18) -0.01017(10) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.569148 0.780970 -0.034389 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2694(3) 0.69591(16) -0.03521(10) 0.0318(4) Uani 1 1 d . . . . .
C6 C 0.0412(3) 0.69767(18) 0.00110(11) 0.0368(4) Uani 1 1 d . . . . .
H6 H -0.056559 0.642304 -0.016998 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0096(3) 0.93274(17) 0.14847(9) 0.0325(4) Uani 1 1 d . . . . .
C11 C -0.2336(3) 0.94882(17) 0.18399(10) 0.0331(4) Uani 1 1 d . . . . .
H11 H -0.371(3) 0.9093(18) 0.1778(10) 0.033(4) Uiso 1 1 d . . . . .
C12 C -0.4256(3) 1.07786(18) 0.29794(10) 0.0383(4) Uani 1 1 d . . . . .
H12A H -0.566072 1.110086 0.267052 0.057 Uiso 1 1 calc R U . . .
H12B H -0.389527 1.163765 0.316356 0.057 Uiso 1 1 calc R U . . .
C13 C -0.4717(3) 0.94924(17) 0.37868(10) 0.0338(4) Uani 1 1 d . . . . .
C14 C -0.2974(3) 0.8405(2) 0.41089(11) 0.0438(4) Uani 1 1 d . . . . .
H14 H -0.145670 0.845666 0.381696 0.061 Uiso 1 1 calc R U . . .
C15 C -0.3418(3) 0.7241(2) 0.48517(12) 0.0500(5) Uani 1 1 d . . . . .
H15 H -0.220905 0.649433 0.506324 0.070 Uiso 1 1 calc R U . . .
C16 C -0.5605(3) 0.7163(2) 0.52854(11) 0.0490(5) Uani 1 1 d . . . . .
H16 H -0.591137 0.636854 0.579829 0.069 Uiso 1 1 calc R U . . .
C17 C -0.7345(3) 0.8248(2) 0.49679(12) 0.0527(5) Uani 1 1 d . . . . .
H17 H -0.885731 0.820413 0.526542 0.074 Uiso 1 1 calc R U . . .
C18 C -0.6905(3) 0.9397(2) 0.42204(11) 0.0460(4) Uani 1 1 d . . . . .
H18 H -0.812303 1.013066 0.400262 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6133(3) 0.53497(17) -0.19320(10) 0.0334(4) Uani 1 1 d . . . . .
C22 C 0.4777(3) 0.44395(18) -0.21513(10) 0.0386(4) Uani 1 1 d . . . . .
H22 H 0.328615 0.428272 -0.184992 0.054 Uiso 1 1 calc R U . . .
C23 C 0.5629(3) 0.37661(19) -0.28142(11) 0.0435(4) Uani 1 1 d . . . . .
H23 H 0.470709 0.315382 -0.297504 0.061 Uiso 1 1 calc R U . . .
C24 C 0.7809(3) 0.3975(2) -0.32455(11) 0.0447(4) Uani 1 1 d . . . . .
H24 H 0.837896 0.350695 -0.370030 0.063 Uiso 1 1 calc R U . . .
C25 C 0.9152(3) 0.4858(2) -0.30169(12) 0.0481(5) Uani 1 1 d . . . . .
H25 H 1.065346 0.499625 -0.331227 0.067 Uiso 1 1 calc R U . . .
C26 C 0.8326(3) 0.5549(2) -0.23570(11) 0.0437(4) Uani 1 1 d . . . . .
H26 H 0.925894 0.615565 -0.219701 0.061 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
N1 C6 1.336(2) . ?
N1 C2 1.341(2) . ?
N8 N9 1.3164(19) . ?
N8 C7 1.362(2) . ?
N9 N10 1.3467(19) . ?
N10 C11 1.342(2) . ?
N10 C12 1.4591(19) . ?
N19 N20 1.2557(18) . ?
N19 C5 1.426(2) . ?
N20 C21 1.428(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.470(2) . ?
C3 C4 1.371(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C11 1.368(2) . ?
C11 H11 0.966(17) . ?
C12 C13 1.513(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.377(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C21 C26 1.384(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 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
C6 N1 C2 116.79(14) . . ?
N9 N8 C7 108.55(13) . . ?
N8 N9 N10 107.24(13) . . ?
C11 N10 N9 110.84(13) . . ?
C11 N10 C12 127.86(14) . . ?
N9 N10 C12 120.99(13) . . ?
N20 N19 C5 112.93(13) . . ?
N19 N20 C21 114.42(14) . . ?
N1 C2 C3 122.82(14) . . ?
N1 C2 C7 116.35(14) . . ?
C3 C2 C7 120.83(15) . . ?
C4 C3 C2 119.61(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.32(15) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 118.44(14) . . ?
C4 C5 N19 125.27(14) . . ?
C6 C5 N19 116.26(14) . . ?
N1 C6 C5 124.01(15) . . ?
N1 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
N8 C7 C11 108.45(14) . . ?
N8 C7 C2 122.63(14) . . ?
C11 C7 C2 128.91(15) . . ?
N10 C11 C7 104.92(14) . . ?
N10 C11 H11 122.1(9) . . ?
C7 C11 H11 133.0(9) . . ?
N10 C12 C13 112.01(12) . . ?
N10 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N10 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C18 C13 C14 118.74(15) . . ?
C18 C13 C12 119.95(14) . . ?
C14 C13 C12 121.30(15) . . ?
C13 C14 C15 120.68(16) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.18(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.30(17) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.42(17) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.67(16) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C26 C21 C22 120.45(15) . . ?
C26 C21 N20 114.90(15) . . ?
C22 C21 N20 124.65(14) . . ?
C23 C22 C21 119.01(16) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.64(17) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.04(16) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.22(17) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.63(17) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?

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
C7 N8 N9 N10 -0.71(17) . . . . ?
N8 N9 N10 C11 0.65(17) . . . . ?
N8 N9 N10 C12 174.74(12) . . . . ?
C5 N19 N20 C21 -178.29(12) . . . . ?
C6 N1 C2 C3 0.2(2) . . . . ?
C6 N1 C2 C7 179.66(13) . . . . ?
N1 C2 C3 C4 0.1(2) . . . . ?
C7 C2 C3 C4 -179.40(14) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C5 N19 179.18(14) . . . . ?
N20 N19 C5 C4 1.8(2) . . . . ?
N20 N19 C5 C6 179.95(13) . . . . ?
C2 N1 C6 C5 0.3(2) . . . . ?
C4 C5 C6 N1 -0.9(2) . . . . ?
N19 C5 C6 N1 -179.16(14) . . . . ?
N9 N8 C7 C11 0.52(17) . . . . ?
N9 N8 C7 C2 179.38(13) . . . . ?
N1 C2 C7 N8 177.22(13) . . . . ?
C3 C2 C7 N8 -3.3(2) . . . . ?
N1 C2 C7 C11 -4.2(2) . . . . ?
C3 C2 C7 C11 175.35(15) . . . . ?
N9 N10 C11 C7 -0.32(16) . . . . ?
C12 N10 C11 C7 -173.90(14) . . . . ?
N8 C7 C11 N10 -0.12(17) . . . . ?
C2 C7 C11 N10 -178.88(14) . . . . ?
C11 N10 C12 C13 73.97(19) . . . . ?
N9 N10 C12 C13 -99.02(17) . . . . ?
N10 C12 C13 C18 -151.46(15) . . . . ?
N10 C12 C13 C14 29.1(2) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 C15 179.50(16) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C12 C13 C18 C17 -178.71(16) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
N19 N20 C21 C26 171.42(14) . . . . ?
N19 N20 C21 C22 -8.0(2) . . . . ?
C26 C21 C22 C23 -1.6(2) . . . . ?
N20 C21 C22 C23 177.86(14) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C22 C21 C26 C25 1.3(3) . . . . ?
N20 C21 C26 C25 -178.20(15) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033

