# 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0178P)^2^+0.3979P] where P=(Fo^2^+2Fc^2^)/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 . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.01807(10) 0.01310(9) 0.02382(10) 0.00003(14) 0.01060(7) -0.00049(13) Cl1 0.0300(4) 0.0155(4) 0.0432(5) 0.0020(3) 0.0205(4) -0.0023(3) Cl2 0.0230(4) 0.0176(4) 0.0316(4) -0.0023(3) 0.0146(3) 0.0000(3) N1 0.0221(16) 0.0162(17) 0.0238(15) 0.0021(11) 0.0100(12) -0.0015(11) N2 0.0231(15) 0.0161(14) 0.0269(15) 0.0012(11) 0.0094(12) -0.0042(11) N3 0.0238(16) 0.0185(16) 0.0246(16) 0.0010(12) 0.0126(13) -0.0013(13) N7 0.0211(16) 0.0167(15) 0.0258(16) 0.0024(12) 0.0096(13) 0.0006(13) N18 0.0238(15) 0.0240(15) 0.0320(15) 0.0029(12) 0.0158(12) 0.0009(12) N19 0.0216(14) 0.0271(15) 0.0266(15) -0.0005(12) 0.0127(12) 0.0006(12) C4 0.0230(17) 0.0183(16) 0.0247(16) -0.0002(13) 0.0112(14) -0.0019(13) C5 0.015(2) 0.0119(13) 0.0230(15) 0.0000(14) 0.0063(16) 0.0031(11) C6 0.0148(16) 0.0202(17) 0.0229(16) 0.0031(13) 0.0078(13) -0.0040(13) C8 0.0234(16) 0.0192(16) 0.0268(17) 0.0017(13) 0.0100(14) -0.0021(14) C9 0.0223(16) 0.0246(18) 0.0256(17) 0.0022(14) 0.0104(14) 0.0021(14) C10 0.0244(17) 0.0220(18) 0.0268(17) 0.0008(14) 0.0124(14) 0.0036(14) C11 0.0246(19) 0.0197(18) 0.027(2) -0.0017(14) 0.0094(16) -0.0019(14) C12 0.0314(19) 0.0188(18) 0.0298(18) 0.0032(14) 0.0184(15) -0.0046(14) C13 0.0274(17) 0.0270(18) 0.0250(17) -0.0012(14) 0.0133(15) -0.0059(14) C14 0.0284(18) 0.0267(19) 0.0304(18) -0.0008(15) 0.0153(15) -0.0049(15) C15 0.0272(18) 0.0291(18) 0.0274(18) -0.0003(14) 0.0145(15) -0.0053(14) C16 0.0298(19) 0.040(2) 0.0298(19) -0.0059(17) 0.0169(16) -0.0067(17) C17 0.032(2) 0.045(2) 0.048(2) 0.0048(19) 0.0217(19) -0.0010(18) C20 0.0216(16) 0.0213(17) 0.0265(16) 0.0041(13) 0.0122(13) 0.0030(13) C21 0.0289(18) 0.0216(17) 0.0301(18) -0.0023(14) 0.0138(15) 0.0013(14) C22 0.0251(17) 0.0234(17) 0.0365(19) 0.0005(15) 0.0107(15) -0.0035(14) C23 0.0223(16) 0.0282(18) 0.0322(18) 0.0071(15) 0.0128(14) -0.0018(14) C24 0.0290(18) 0.0317(19) 0.0295(19) 0.0010(15) 0.0182(16) 0.0040(15) C25 0.0261(17) 0.0284(18) 0.0226(17) -0.0050(14) 0.0118(14) -0.0038(14) _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 _shelx_res_file ; TITL alap_a.res in Pc shelx.res created by SHELXL-2018/3 at 11:49:46 on 24-Nov-2020 REM Old TITL alap in P2/a #13 REM SHELXT solution in Pc: R1 0.134, Rweak 0.054, Alpha 0.023 REM 1.780 for 143 systematic absences, Orientation a'=c, b'=-b, c'=a REM Flack x = 0.142 ( 0.008 ) from 2052 Parsons' quotients REM Formula found by SHELXT: C22 N19 Pd CELL 0.71075 12.883 8.8827 9.6095 90 110.352 90 ZERR 2 0.0007 0.0004 0.0005 0 0.008 0 LATT -1 SYMM +X,-Y,0.5+Z SFAC C H Cl N Pd UNIT 38 44 4 12 2 L.S. 3 PLAN 9 SIZE 0.5 0.25 0.02 TEMP -130 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta SHEL 99999 0.8 WGHT 0.017800 0.397900 FVAR 0.28855 PD1 5 0.503880 0.398959 0.463960 11.00000 0.01807 0.01310 = 0.02382 0.00003 0.01060 -0.00049 CL1 3 0.424972 0.190720 0.525199 11.00000 0.02998 0.01546 = 0.04318 0.00197 0.02050 -0.00226 CL2 3 0.621818 0.252069 0.391192 11.00000 0.02295 0.01761 = 0.03158 -0.00229 0.01464 -0.00005 N1 4 0.564501 0.594572 0.421045 11.00000 0.02212 0.01622 = 0.02381 0.00211 0.00995 -0.00152 N2 4 0.633893 0.634182 0.357551 11.00000 0.02314 0.01605 = 0.02692 0.00122 0.00940 -0.00420 N3 4 0.640254 0.785182 0.366907 11.00000 0.02377 0.01846 = 0.02455 0.00101 0.01262 -0.00130 N7 4 0.408446 0.546582 0.531350 11.00000 0.02111 0.01675 = 0.02575 0.00244 0.00959 0.00058 N18 4 0.169022 0.571249 0.647504 11.00000 0.02382 0.02400 = 0.03199 0.00293 0.01577 0.00091 N19 4 0.128839 0.670625 0.707003 11.00000 0.02160 0.02712 = 0.02663 -0.00050 0.01268 0.00060 C4 1 0.574397 0.841130 0.435453 11.00000 0.02303 0.01833 = 0.02474 -0.00016 0.01123 -0.00194 AFIX 43 H4 2 0.564240 0.943871 0.455029 11.00000 -1.20000 AFIX 0 C5 1 0.525268 0.719139 0.470926 11.00000 0.01516 0.01194 = 0.02302 0.00000 0.00629 0.00309 C6 1 0.440431 0.692045 0.536286 11.00000 0.01484 0.02017 = 0.02293 0.00311 0.00779 -0.00401 C8 1 0.322037 0.511612 0.572430 11.00000 0.02342 0.01918 = 0.02682 0.00169 0.01004 -0.00206 AFIX 43 H8 2 0.298179 0.409881 0.566889 11.00000 -1.20000 AFIX 0 C9 1 0.266663 0.620992 0.622920 11.00000 0.02225 0.02460 = 0.02560 0.00219 0.01043 0.00205 C10 1 0.303028 0.769871 0.636689 11.00000 0.02441 0.02195 = 0.02679 0.00081 0.01244 0.00360 AFIX 43 H10 2 0.268329 0.844999 0.675721 11.00000 -1.20000 AFIX 0 C11 1 0.390722 0.804726 0.592025 11.00000 0.02460 0.01967 = 0.02655 -0.00167 0.00943 -0.00189 AFIX 43 H11 2 0.417222 0.905266 0.599205 11.00000 -1.20000 AFIX 0 C12 1 0.707561 0.864747 0.294110 11.00000 0.03140 0.01878 = 0.02981 0.00320 0.01838 -0.00456 AFIX 23 H12A 2 0.697903 0.974552 0.302414 11.00000 -1.20000 H12B 2 0.680101 0.838679 0.187275 11.00000 -1.20000 AFIX 0 C13 1 0.830172 0.827318 0.359672 11.00000 0.02742 0.02704 = 0.02497 -0.00118 0.01332 -0.00585 AFIX 23 H13A 2 0.840025 0.717098 0.373211 11.00000 -1.20000 H13B 2 0.863028 0.875878 0.458018 11.00000 -1.20000 AFIX 0 C14 1 0.888630 0.883363 0.255613 11.00000 0.02843 0.02667 = 0.03045 -0.00081 0.01526 -0.00487 AFIX 23 H14A 2 0.877376 0.993439 0.242594 11.00000 -1.20000 H14B 2 0.853505 0.835801 0.157189 11.00000 -1.20000 AFIX 0 C15 1 1.012926 0.850687 0.309710 11.00000 0.02715 0.02910 = 0.02744 -0.00029 0.01450 -0.00529 AFIX 23 H15A 2 1.050439 0.909739 0.400760 11.00000 -1.20000 H15B 2 1.025611 0.742590 0.334997 11.00000 -1.20000 AFIX 0 C16 1 1.062618 0.890485 0.192011 11.00000 0.02979 0.03957 = 0.02975 -0.00590 0.01690 -0.00672 AFIX 23 H16A 2 1.051811 0.999445 0.170094 11.00000 -1.20000 H16B 2 1.021782 0.835200 0.099708 11.00000 -1.20000 AFIX 0 C17 1 1.185419 0.854337 0.235909 11.00000 0.03193 0.04517 = 0.04833 0.00482 0.02172 -0.00101 AFIX 137 H17A 2 1.209530 0.872821 0.151287 11.00000 -1.50000 H17B 2 1.197954 0.748391 0.265444 11.00000 -1.50000 H17C 2 1.227787 0.918541 0.319241 11.00000 -1.50000 AFIX 0 C20 1 0.023271 0.632402 0.715087 11.00000 0.02158 0.02127 = 0.02652 0.00407 0.01225 0.00305 C21 1 -0.045114 0.521476 0.628132 11.00000 0.02892 0.02164 = 0.03007 -0.00227 0.01382 0.00135 AFIX 43 H21 2 -0.019843 0.459671 0.565749 11.00000 -1.20000 AFIX 0 C22 1 -0.149902 0.501926 0.633198 11.00000 0.02513 0.02337 = 0.03653 0.00048 0.01069 -0.00346 AFIX 43 H22 2 -0.197225 0.427060 0.573106 11.00000 -1.20000 AFIX 0 C23 1 -0.186731 0.590547 0.725184 11.00000 0.02228 0.02823 = 0.03225 0.00707 0.01278 -0.00182 AFIX 43 H23 2 -0.258619 0.575298 0.729214 11.00000 -1.20000 AFIX 0 C24 1 -0.118671 0.701482 0.811350 11.00000 0.02896 0.03167 = 0.02953 0.00103 0.01821 0.00400 AFIX 43 H24 2 -0.143984 0.762149 0.874489 11.00000 -1.20000 AFIX 0 C25 1 -0.013535 0.724231 0.805666 11.00000 0.02608 0.02839 = 0.02260 -0.00498 0.01176 -0.00380 AFIX 43 H25 2 0.032697 0.801620 0.862985 11.00000 -1.20000 AFIX 0 HKLF 4 REM alap_a.res in Pc REM wR2 = 0.0375, GooF = S = 1.110, Restrained GooF = 1.109 for all data REM R1 = 0.0183 for 4187 Fo > 4sig(Fo) and 0.0184 for all 4202 data REM 254 parameters refined using 2 restraints END WGHT 0.0178 0.3979 REM Highest difference peak 0.336, deepest hole -0.380, 1-sigma level 0.065 Q1 1 0.5059 1.0021 0.4607 11.00000 0.05 0.34 Q2 1 0.4401 0.3974 0.3793 11.00000 0.05 0.32 Q3 1 0.5065 0.3006 0.4512 11.00000 0.05 0.32 Q4 1 0.4412 0.3817 0.4832 11.00000 0.05 0.31 Q5 1 0.5581 0.7893 0.4957 11.00000 0.05 0.31 Q6 1 0.7599 0.8311 0.3090 11.00000 0.05 0.30 Q7 1 0.6369 0.8626 0.3840 11.00000 0.05 0.30 Q8 1 0.4193 0.7719 0.5365 11.00000 0.05 0.29 Q9 1 0.3846 0.8629 0.5508 11.00000 0.05 0.29 ; _shelx_res_checksum 57601 ####################################################################### # # 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0372P)^2^+0.3023P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0316(7) 0.0347(7) 0.0441(8) -0.0151(6) 0.0003(6) -0.0072(6) N8 0.0417(8) 0.0441(8) 0.0366(7) -0.0140(6) -0.0034(6) -0.0109(6) N9 0.0452(8) 0.0460(8) 0.0369(7) -0.0144(6) -0.0045(6) -0.0124(7) N10 0.0395(7) 0.0339(7) 0.0298(6) -0.0082(5) -0.0050(5) -0.0059(6) N19 0.0311(7) 0.0339(7) 0.0407(7) -0.0106(6) -0.0029(6) -0.0015(6) N20 0.0323(7) 0.0370(7) 0.0400(7) -0.0109(6) -0.0006(6) -0.0046(6) C2 0.0334(8) 0.0295(8) 0.0286(7) -0.0031(6) -0.0057(6) -0.0045(6) C3 0.0353(9) 0.0430(9) 0.0331(8) -0.0101(7) -0.0063(6) -0.0109(7) C4 0.0281(8) 0.0431(9) 0.0356(8) -0.0077(7) -0.0034(6) -0.0048(7) C5 0.0306(8) 0.0287(8) 0.0343(8) -0.0058(6) -0.0045(6) -0.0020(6) C6 0.0335(9) 0.0332(8) 0.0467(9) -0.0150(7) -0.0024(7) -0.0068(7) C7 0.0359(8) 0.0317(8) 0.0290(7) -0.0037(6) -0.0068(6) -0.0069(7) C11 0.0380(9) 0.0330(8) 0.0298(8) -0.0082(6) -0.0061(6) -0.0072(7) C12 0.0445(9) 0.0365(9) 0.0342(8) -0.0124(7) -0.0050(7) 0.0019(7) C13 0.0388(9) 0.0359(8) 0.0300(8) -0.0150(7) -0.0046(6) -0.0014(7) C14 0.0375(9) 0.0452(10) 0.0425(9) -0.0055(8) -0.0010(7) -0.0006(8) C15 0.0520(11) 0.0451(10) 0.0445(10) -0.0018(8) -0.0060(8) 0.0022(9) C16 0.0590(12) 0.0504(11) 0.0356(9) -0.0066(8) -0.0004(8) -0.0147(9) C17 0.0419(10) 0.0695(13) 0.0448(10) -0.0154(9) 0.0060(8) -0.0103(9) C18 0.0403(10) 0.0543(11) 0.0424(9) -0.0162(8) -0.0048(7) 0.0047(8) C21 0.0339(8) 0.0305(8) 0.0337(8) -0.0069(6) -0.0030(6) -0.0013(6) C22 0.0391(9) 0.0380(9) 0.0375(8) -0.0077(7) -0.0011(7) -0.0084(7) C23 0.0524(11) 0.0387(9) 0.0419(9) -0.0128(8) -0.0083(8) -0.0065(8) C24 0.0510(11) 0.0431(10) 0.0383(9) -0.0140(8) -0.0046(8) 0.0073(8) C25 0.0370(9) 0.0583(12) 0.0472(10) -0.0174(9) 0.0030(8) -0.0006(8) C26 0.0367(9) 0.0495(10) 0.0475(10) -0.0179(8) -0.0001(7) -0.0073(8) _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 _shelx_res_file ; TITL S1886_2 New:P-1 shelx.res created by SHELXL-2018/3 at 11:31:31 on 24-Nov-2020 CELL 1.54187 5.8998 9.3629 15.9508 73.354 81.870 81.835 ZERR 2.00 0.0002 0.0003 0.0006 0.005 0.006 0.006 LATT 1 SFAC C H N UNIT 40 32 12 MERG 2 FMAP 2 PLAN 10 SIZE 0.130 0.400 0.400 ACTA BOND $H htab CONF L.S. 3 TEMP -120.00 WGHT 0.037200 0.302300 EXTI 0.005607 FVAR 4.54462 N1 3 -0.049363 0.772469 0.059951 11.00000 0.03161 0.03466 = 0.04413 -0.01507 0.00029 -0.00719 N8 3 0.116045 1.011209 0.181519 11.00000 0.04170 0.04410 = 0.03658 -0.01397 -0.00341 -0.01086 N9 3 -0.022002 1.073760 0.236521 11.00000 0.04523 0.04596 = 0.03686 -0.01443 -0.00449 -0.01238 N10 3 -0.234791 1.036502 0.237509 11.00000 0.03950 0.03386 = 0.02975 -0.00824 -0.00501 -0.00591 N19 3 0.335008 0.611539 -0.098003 11.00000 0.03107 0.03388 = 0.04068 -0.01060 -0.00286 -0.00149 N20 3 0.543213 0.614821 -0.128206 11.00000 0.03234 0.03696 = 0.04000 -0.01092 -0.00062 -0.00461 C2 1 0.092087 0.850180 0.084096 11.00000 0.03337 0.02952 = 0.02863 -0.00308 -0.00570 -0.00450 C3 1 0.322793 0.855056 0.050428 11.00000 0.03526 0.04300 = 0.03313 -0.01010 -0.00629 -0.01092 AFIX 43 H3 2 0.417343 0.911381 0.069335 11.00000 -1.40000 AFIX 0 C4 1 0.412665 0.778072 -0.010175 11.00000 0.02806 0.04314 = 0.03556 -0.00768 -0.00344 -0.00482 AFIX 43 H4 2 0.569148 0.780970 -0.034389 11.00000 -1.40000 AFIX 0 C5 1 0.269369 0.695910 -0.035208 11.00000 0.03062 0.02874 = 0.03433 -0.00580 -0.00452 -0.00201 C6 1 0.041211 0.697668 0.001098 11.00000 0.03354 0.03324 = 0.04670 -0.01498 -0.00241 -0.00683 AFIX 43 H6 2 -0.056559 0.642304 -0.016998 11.00000 -1.40000 AFIX 0 C7 1 -0.009577 0.932740 0.148466 11.00000 0.03586 0.03166 = 0.02899 -0.00372 -0.00681 -0.00685 C11 1 -0.233553 0.948819 0.183986 11.00000 0.03798 0.03297 = 0.02983 -0.00820 -0.00610 -0.00719 H11 2 -0.371002 0.909295 0.177771 11.00000 0.03286 C12 1 -0.425574 1.077863 0.297935 11.00000 0.04446 0.03651 = 0.03418 -0.01243 -0.00505 0.00190 AFIX 23 H12A 2 -0.566072 1.110086 0.267052 11.00000 -1.50000 H12B 2 -0.389527 1.163765 0.316356 11.00000 -1.50000 AFIX 0 C13 1 -0.471717 0.949237 0.378679 11.00000 0.03878 0.03592 = 0.03000 -0.01495 -0.00461 -0.00136 C14 1 -0.297448 0.840461 0.410887 11.00000 0.03749 0.04525 = 0.04249 -0.00552 -0.00102 -0.00057 AFIX 43 H14 2 -0.145670 0.845666 0.381696 11.00000 -1.40000 AFIX 0 C15 1 -0.341761 0.724122 0.485174 11.00000 0.05198 0.04507 = 0.04448 -0.00177 -0.00600 0.00223 AFIX 43 H15 2 -0.220905 0.649433 0.506324 11.00000 -1.40000 AFIX 0 C16 1 -0.560471 0.716253 0.528544 11.00000 0.05905 0.05043 = 0.03556 -0.00663 -0.00044 -0.01465 AFIX 43 H16 2 -0.591137 0.636854 0.579829 11.00000 -1.40000 AFIX 0 C17 1 -0.734499 0.824773 0.496787 11.00000 0.04190 0.06949 = 0.04480 -0.01539 0.00603 -0.01025 AFIX 43 H17 2 -0.885731 0.820413 0.526542 11.00000 -1.40000 AFIX 0 C18 1 -0.690475 0.939732 0.422037 11.00000 0.04026 0.05428 = 0.04245 -0.01618 -0.00478 0.00474 AFIX 43 H18 2 -0.812303 1.013066 0.400262 11.00000 -1.40000 AFIX 0 C21 1 0.613288 0.534972 -0.193199 11.00000 0.03394 0.03045 = 0.03370 -0.00688 -0.00300 -0.00130 C22 1 0.477659 0.443952 -0.215127 11.00000 0.03908 0.03795 = 0.03749 -0.00766 -0.00109 -0.00842 AFIX 43 H22 2 0.328615 0.428272 -0.184992 11.00000 -1.40000 AFIX 0 C23 1 0.562888 0.376612 -0.281421 11.00000 0.05245 0.03871 = 0.04191 -0.01278 -0.00826 -0.00647 AFIX 43 H23 2 0.470709 0.315382 -0.297504 11.00000 -1.40000 AFIX 0 C24 1 0.780923 0.397486 -0.324549 11.00000 0.05101 0.04306 = 0.03828 -0.01403 -0.00463 0.00727 AFIX 43 H24 2 0.837896 0.350695 -0.370030 11.00000 -1.40000 AFIX 0 C25 1 0.915247 0.485826 -0.301689 11.00000 0.03699 0.05834 = 0.04724 -0.01737 0.00300 -0.00062 AFIX 43 H25 2 1.065346 0.499625 -0.331227 11.00000 -1.40000 AFIX 0 C26 1 0.832601 0.554883 -0.235700 11.00000 0.03672 0.04948 = 0.04752 -0.01791 -0.00007 -0.00732 AFIX 43 H26 2 0.925894 0.615565 -0.219701 11.00000 -1.40000 AFIX 0 HKLF 4 REM S1886_2 New:P-1 REM wR2 = 0.1081, GooF = S = 1.105, Restrained GooF = 1.105 for all data REM R1 = 0.0432 for 2720 Fo > 4sig(Fo) and 0.0484 for all 2979 data REM 240 parameters refined using 0 restraints END WGHT 0.0374 0.3016 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.163, deepest hole -0.150, 1-sigma level 0.033 Q1 1 0.1472 0.7388 -0.0384 11.00000 0.05 0.16 Q2 1 0.0396 0.8866 0.1229 11.00000 0.05 0.16 Q3 1 -0.3220 1.1679 0.3032 11.00000 0.05 0.14 Q4 1 0.6188 0.7305 -0.1378 11.00000 0.05 0.14 Q5 1 -0.1808 0.7429 0.0977 11.00000 0.05 0.14 Q6 1 -0.4005 0.8780 0.3757 11.00000 0.05 0.14 Q7 1 -0.0864 0.8784 0.1814 11.00000 0.05 0.14 Q8 1 0.1907 0.5462 -0.0851 11.00000 0.05 0.13 Q9 1 0.2005 0.6619 0.0050 11.00000 0.05 0.13 Q10 1 0.6363 0.6970 -0.1265 11.00000 0.05 0.13 ; _shelx_res_checksum 41038