#------------------------------------------------------------------------------ #$Date: 2024-04-05 03:57:13 +0300 (Fri, 05 Apr 2024) $ #$Revision: 291078 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248383.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7248383 loop_ _publ_author_name 'Kumar, Krishan' 'Karmakar, Anirban' 'Thakur, Diksha' 'Sharma, Dipanshu' 'Chen, Feng-Rong' 'Verma, Varsha' 'Nagar, Mangey Ram' 'Jou, Jwo-Huei' 'Banik, Subrata' 'Ghosh, Subrata' _publ_section_title ; Self-assembled molecular network with waterwheel-like architecture: experimental and theoretical evaluation toward electron transport capabilities for optoelectronic devices. ; _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_paper_doi 10.1039/d4cp00390j _journal_year 2024 _chemical_formula_sum 'C33 H15 N9 O3' _chemical_formula_weight 585.54 _space_group_crystal_system trigonal _space_group_IT_number 148 _space_group_name_Hall '-R 3' _space_group_name_H-M_alt 'R -3 :H' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2023-07-31 deposited with the CCDC. 2024-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 12 _cell_length_a 23.8757(6) _cell_length_b 23.8757(6) _cell_length_c 17.6972(5) _cell_measurement_reflns_used 3562 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 66.4410 _cell_measurement_theta_min 3.2890 _cell_volume 8736.7(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.948 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0369 _diffrn_reflns_Laue_measured_fraction_full 0.948 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 9227 _diffrn_reflns_point_group_measured_fraction_full 0.948 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 67.091 _diffrn_reflns_theta_min 3.287 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SABADS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_description Plates _exptl_crystal_F_000 3600 _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.487 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 3327 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.984 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0682 _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/[\s^2^(Fo^2^)+(0.1308P)^2^+7.4086P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1993 _refine_ls_wR_factor_ref 0.2149 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2656 _reflns_number_total 3327 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp00390j2.cif _cod_data_source_block TCmCN _cod_original_cell_volume 8736.7(5) _cod_database_code 7248383 _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. ; _shelx_estimated_absorpt_t_min 0.847 _shelx_estimated_absorpt_t_max 0.922 _shelxl_version_number 2014/6 _shelx_res_file ; TITL kk_54b_rt_cu_a.res in R-3 CELL 1.54184 23.8757 23.8757 17.6972 90.000 90.000 120.000 ZERR 12.00 0.0006 0.0006 0.0005 0.000 0.000 0.000 LATT 3 SYMM - Y, X - Y, Z SYMM - X + Y, - X, Z SFAC C H N O UNIT 396 180 108 36 MERG 2 MORE -1 FMAP 2 OMIT 5 8 15 OMIT 6 9 15 OMIT 8 8 15 OMIT 4 7 15 PLAN 10 ACTA HTAB BOND $H CONF SIZe 0.23 0.15 0.11 TEMP 23.0 LIST 4 L.S. 20 WGHT 0.130800 7.408600 FVAR 1.65354 O7 4 0.567281 0.350564 0.426737 11.00000 0.05825 0.06121 = 0.07537 -0.00244 0.00126 0.03198 N3 3 0.677453 0.395462 0.427077 11.00000 0.05994 0.05758 = 0.03942 -0.00178 -0.00160 0.02966 O22 4 0.883551 0.983610 0.288741 11.00000 0.07358 0.07757 = 0.07715 0.01467 -0.00381 0.03844 N6 3 0.948372 0.937982 0.289486 11.00000 0.07403 0.07386 = 0.04232 -0.00212 -0.00799 0.03632 C11 1 0.619330 0.343491 0.427263 11.00000 0.05797 0.06154 = 0.03166 -0.00104 -0.00003 0.03089 C1 1 0.576370 0.413534 0.428767 11.00000 0.05221 0.06172 = 0.06475 0.00142 0.00378 0.03024 C22 1 0.942831 0.990344 0.289904 11.00000 0.07402 0.07654 = 0.03397 0.00681 -0.00186 0.03892 C3 1 0.585868 0.501938 0.501712 11.00000 0.06542 0.06428 = 0.05846 0.00262 0.00396 0.03308 C2 1 0.581556 0.441640 0.497485 11.00000 0.07424 0.06759 = 0.05436 0.00593 -0.00063 0.03895 AFIX 43 H2 2 0.582210 0.420589 0.541408 11.00000 -1.20000 AFIX 0 C14 1 0.829124 0.921558 0.297865 11.00000 0.06948 0.07884 = 0.06543 0.00392 -0.00330 0.04081 C6 1 0.574951 0.442057 0.362630 11.00000 0.07728 0.08346 = 0.05485 0.00489 0.01260 0.04644 AFIX 43 H6 2 0.570726 0.421687 0.316473 11.00000 -1.20000 AFIX 0 C4 1 0.585183 0.531888 0.434355 11.00000 0.07848 0.06705 = 0.07097 0.01129 0.01424 0.04164 AFIX 43 H4 2 0.588272 0.572282 0.435558 11.00000 -1.20000 AFIX 0 C5 1 0.579985 0.502144 0.366384 11.00000 0.09939 0.08837 = 0.05505 0.02016 0.01851 0.05629 AFIX 43 H5 2 0.579847 0.522853 0.321934 11.00000 -1.20000 AFIX 0 C13 1 0.814868 0.895401 0.369042 11.00000 0.07444 0.08119 = 0.06404 0.00280 -0.00244 0.03837 AFIX 43 H13 2 0.842134 0.917223 0.409349 11.00000 -1.20000 AFIX 0 C7 1 0.589666 0.527244 0.577224 11.00000 0.08933 0.07678 = 0.06459 -0.00071 -0.00100 0.04207 AFIX 43 H7 2 0.591885 0.501721 0.615485 11.00000 -1.20000 AFIX 0 C8 1 0.590550 0.580558 0.601673 11.00000 0.07480 0.07911 = 0.06866 -0.01102 0.00336 0.03494 C12 1 0.759110 0.835776 0.380429 11.00000 0.07251 0.08062 = 0.07573 -0.00065 0.00459 0.03778 C10 1 0.590240 0.629190 0.554981 11.00000 0.08350 0.08218 = 0.08349 -0.01117 0.00297 0.04408 N1 3 0.590597 0.669755 0.520458 11.00000 0.14877 0.10190 = 0.11303 0.00139 0.00241 0.07865 C15 1 0.791182 0.891914 0.236850 11.00000 0.08848 0.10494 = 0.06781 -0.00497 -0.01485 0.04887 AFIX 43 H15 2 0.801888 0.910844 0.189210 11.00000 -1.20000 AFIX 0 C17 1 0.720888 0.805325 0.319011 11.00000 0.07665 0.08747 = 0.09683 -0.00836 -0.00140 0.03809 AFIX 43 H17 2 0.683806 0.765271 0.325494 11.00000 -1.20000 AFIX 0 C19 1 0.764194 0.824424 0.522527 11.00000 0.10937 0.10016 = 0.07421 0.01127 0.01868 0.05999 C18 1 0.740713 0.802683 0.454101 11.00000 0.08462 0.08834 = 0.09365 0.01168 0.01535 0.03764 AFIX 43 H18 2 0.707444 0.759867 0.452361 11.00000 -1.20000 AFIX 0 C16 1 0.735895 0.832395 0.248129 11.00000 0.09155 0.11651 = 0.08891 -0.03300 -0.03052 0.05209 AFIX 43 H16 2 0.708899 0.810749 0.207560 11.00000 -1.20000 AFIX 0 N2 3 0.591679 0.597681 0.745411 11.00000 0.17840 0.14881 = 0.07913 -0.02218 0.00618 0.08770 C9 1 0.591383 0.591035 0.681562 11.00000 0.11457 0.09991 = 0.07616 -0.01226 0.00346 0.05561 N4 3 0.726568 0.749427 0.638780 11.00000 0.13658 0.17299 = 0.11047 0.05433 0.03981 0.08113 C20 1 0.742443 0.781509 0.587127 11.00000 0.10988 0.13331 = 0.08958 0.02849 0.02936 0.06886 C21 1 0.809912 0.888530 0.540417 11.00000 0.21979 0.10248 = 0.06755 -0.00142 -0.01233 0.07824 N5 3 0.847377 0.940373 0.556283 11.00000 0.41902 0.10287 = 0.10543 -0.02369 -0.08204 0.06471 HKLF 4 REM kk_54b_rt_cu_a.res in R-3 REM R1 = 0.0682 for 2656 Fo > 4sig(Fo) and 0.0830 for all 3327 data REM 271 parameters refined using 0 restraints END WGHT 0.1266 3.3227 REM Instructions for potential hydrogen bonds EQIV $1 x-1/3, y-2/3, z+1/3 HTAB C2 O22_$1 HTAB C13 N5 REM Highest difference peak 0.487, deepest hole -0.211, 1-sigma level 0.049 Q1 1 1.0000 1.0000 0.5264 10.33333 0.05 0.49 Q2 1 0.6533 0.3799 0.4450 11.00000 0.05 0.25 Q3 1 0.6573 0.3694 0.4058 11.00000 0.05 0.24 Q4 1 0.6044 0.4357 0.4635 11.00000 0.05 0.24 Q5 1 0.6194 0.3163 0.4505 11.00000 0.05 0.23 Q6 1 0.6927 0.3924 0.4046 11.00000 0.05 0.23 Q7 1 0.5649 0.4932 0.6282 11.00000 0.05 0.20 Q8 1 0.6132 0.5313 0.3959 11.00000 0.05 0.20 Q9 1 0.5793 0.3886 0.4505 11.00000 0.05 0.19 Q10 1 0.5875 0.3471 0.4503 11.00000 0.05 0.19 ; _shelx_res_checksum 194 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' 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 O7 O 0.56728(8) 0.35056(8) 0.42674(10) 0.0640(5) Uani 1 1 d . . . . . N3 N 0.67745(9) 0.39546(9) 0.42708(9) 0.0522(5) Uani 1 1 d . . . . . O22 O 0.88355(9) 0.98361(9) 0.28874(11) 0.0758(6) Uani 1 1 d . . . . . N6 N 0.94837(11) 0.93798(11) 0.28949(11) 0.0637(6) Uani 1 1 d . . . . . C11 C 0.61933(10) 0.34349(10) 0.42726(11) 0.0499(5) Uani 1 1 d . . . . . C1 C 0.57637(11) 0.41353(11) 0.42877(14) 0.0588(6) Uani 1 1 d . . . . . C22 C 0.94283(12) 0.99034(13) 0.28990(12) 0.0609(6) Uani 1 1 d . . . . . C3 C 0.58587(12) 0.50194(12) 0.50171(14) 0.0624(6) Uani 1 1 d . . . . . C2 C 0.58156(13) 0.44164(12) 0.49749(14) 0.0638(6) Uani 1 1 d . . . . . H2 H 0.5822 0.4206 0.5414 0.077 Uiso 1 1 calc R U . . . C14 C 0.82912(13) 0.92156(14) 0.29787(15) 0.0696(7) Uani 1 1 d . . . . . C6 C 0.57495(13) 0.44206(14) 0.36263(14) 0.0691(7) Uani 1 1 d . . . . . H6 H 0.5707 0.4217 0.3165 0.083 Uiso 1 1 calc R U . . . C4 C 0.58518(13) 0.53189(13) 0.43436(15) 0.0698(7) Uani 1 1 d . . . . . H4 H 0.5883 0.5723 0.4356 0.084 Uiso 1 1 calc R U . . . C5 C 0.57998(16) 0.50214(15) 0.36638(15) 0.0768(8) Uani 1 1 d . . . . . H5 H 0.5798 0.5229 0.3219 0.092 Uiso 1 1 calc R U . . . C13 C 0.81487(14) 0.89540(15) 0.36904(16) 0.0735(7) Uani 1 1 d . . . . . H13 H 0.8421 0.9172 0.4093 0.088 Uiso 1 1 calc R U . . . C7 C 0.58967(15) 0.52724(15) 0.57722(16) 0.0767(7) Uani 1 1 d . . . . . H7 H 0.5919 0.5017 0.6155 0.092 Uiso 1 1 calc R U . . . C8 C 0.59055(14) 0.58056(14) 0.60167(16) 0.0758(7) Uani 1 1 d . . . . . C12 C 0.75911(14) 0.83578(15) 0.38043(17) 0.0765(7) Uani 1 1 d . . . . . C10 C 0.59024(16) 0.62919(17) 0.55498(19) 0.0819(8) Uani 1 1 d . . . . . N1 N 0.5906(2) 0.66975(18) 0.5205(2) 0.1141(11) Uani 1 1 d . . . . . C15 C 0.79118(17) 0.89191(18) 0.23685(18) 0.0868(9) Uani 1 1 d . . . . . H15 H 0.8019 0.9108 0.1892 0.104 Uiso 1 1 calc R U . . . C17 C 0.72089(16) 0.80533(17) 0.3190(2) 0.0883(9) Uani 1 1 d . . . . . H17 H 0.6838 0.7653 0.3255 0.106 Uiso 1 1 calc R U . . . C19 C 0.76419(19) 0.82442(18) 0.52253(19) 0.0912(9) Uani 1 1 d . . . . . C18 C 0.74071(17) 0.80268(18) 0.4541(2) 0.0914(9) Uani 1 1 d . . . . . H18 H 0.7074 0.7599 0.4524 0.110 Uiso 1 1 calc R U . . . C16 C 0.73590(18) 0.8324(2) 0.2481(2) 0.0990(11) Uani 1 1 d . . . . . H16 H 0.7089 0.8107 0.2076 0.119 Uiso 1 1 calc R U . . . N2 N 0.5917(2) 0.5977(2) 0.7454(2) 0.1328(14) Uani 1 1 d . . . . . C9 C 0.5914(2) 0.59104(18) 0.6816(2) 0.0960(10) Uani 1 1 d . . . . . N4 N 0.7266(2) 0.7494(2) 0.6388(2) 0.1384(15) Uani 1 1 d . . . . . C20 C 0.7424(2) 0.7815(2) 0.5871(2) 0.1073(12) Uani 1 1 d . . . . . C21 C 0.8099(3) 0.8885(2) 0.5404(2) 0.1310(18) Uani 1 1 d . . . . . N5 N 0.8474(5) 0.9404(2) 0.5563(3) 0.238(4) Uani 1 1 d . . . . . 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 O7 0.0582(9) 0.0612(9) 0.0754(11) -0.0024(8) 0.0013(8) 0.0320(8) N3 0.0599(11) 0.0576(10) 0.0394(9) -0.0018(7) -0.0016(7) 0.0297(9) O22 0.0736(11) 0.0776(12) 0.0772(12) 0.0147(9) -0.0038(9) 0.0384(9) N6 0.0740(13) 0.0739(13) 0.0423(10) -0.0021(9) -0.0080(9) 0.0363(11) C11 0.0580(12) 0.0615(12) 0.0317(9) -0.0010(8) 0.0000(8) 0.0309(10) C1 0.0522(11) 0.0617(13) 0.0647(14) 0.0014(11) 0.0038(10) 0.0302(10) C22 0.0740(15) 0.0765(16) 0.0340(11) 0.0068(10) -0.0019(10) 0.0389(13) C3 0.0654(14) 0.0643(13) 0.0585(13) 0.0026(11) 0.0040(11) 0.0331(11) C2 0.0742(15) 0.0676(14) 0.0544(13) 0.0059(11) -0.0006(11) 0.0390(12) C14 0.0695(15) 0.0788(16) 0.0654(15) 0.0039(13) -0.0033(12) 0.0408(13) C6 0.0773(16) 0.0835(17) 0.0548(13) 0.0049(12) 0.0126(12) 0.0464(14) C4 0.0785(16) 0.0670(14) 0.0710(16) 0.0113(12) 0.0142(13) 0.0416(13) C5 0.099(2) 0.0884(18) 0.0550(14) 0.0202(13) 0.0185(13) 0.0563(16) C13 0.0744(16) 0.0812(17) 0.0640(15) 0.0028(13) -0.0024(12) 0.0384(14) C7 0.0893(19) 0.0768(17) 0.0646(15) -0.0007(13) -0.0010(14) 0.0421(15) C8 0.0748(16) 0.0791(17) 0.0687(16) -0.0110(14) 0.0034(13) 0.0349(14) C12 0.0725(16) 0.0806(17) 0.0757(17) -0.0007(14) 0.0046(14) 0.0378(14) C10 0.0835(19) 0.0822(19) 0.0835(19) -0.0112(16) 0.0030(15) 0.0441(16) N1 0.149(3) 0.102(2) 0.113(2) 0.0014(19) 0.002(2) 0.079(2) C15 0.088(2) 0.105(2) 0.0678(17) -0.0050(16) -0.0149(15) 0.0489(19) C17 0.0766(18) 0.087(2) 0.097(2) -0.0084(17) -0.0014(16) 0.0381(16) C19 0.109(2) 0.100(2) 0.0742(19) 0.0113(17) 0.0187(17) 0.060(2) C18 0.085(2) 0.088(2) 0.094(2) 0.0117(17) 0.0153(17) 0.0376(16) C16 0.092(2) 0.117(3) 0.089(2) -0.033(2) -0.0305(18) 0.052(2) N2 0.178(4) 0.149(3) 0.079(2) -0.022(2) 0.006(2) 0.088(3) C9 0.115(3) 0.100(2) 0.076(2) -0.0123(17) 0.0035(18) 0.056(2) N4 0.137(3) 0.173(4) 0.110(3) 0.054(3) 0.040(2) 0.081(3) C20 0.110(3) 0.133(3) 0.090(2) 0.028(2) 0.029(2) 0.069(2) C21 0.220(6) 0.102(3) 0.068(2) -0.001(2) -0.012(3) 0.078(3) N5 0.419(11) 0.103(3) 0.105(3) -0.024(2) -0.082(5) 0.065(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O7 C1 118.59(17) . . ? C11 N3 C11 112.2(2) . 3_665 ? C22 O22 C14 119.2(2) . . ? C22 N6 C22 111.9(3) . 2_765 ? N3 C11 N3 127.8(2) . 2_655 ? N3 C11 O7 119.24(19) . . ? N3 C11 O7 112.97(19) 2_655 . ? C6 C1 C2 122.6(2) . . ? C6 C1 O7 118.9(2) . . ? C2 C1 O7 118.4(2) . . ? N6 C22 N6 128.1(3) . 3_675 ? N6 C22 O22 119.0(2) . . ? N6 C22 O22 112.9(2) 3_675 . ? C2 C3 C4 118.1(2) . . ? C2 C3 C7 115.9(2) . . ? C4 C3 C7 126.0(2) . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C15 C14 C13 122.9(3) . . ? C15 C14 O22 118.7(3) . . ? C13 C14 O22 118.2(2) . . ? C1 C6 C5 117.8(2) . . ? C1 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C8 C7 C3 131.6(3) . . ? C8 C7 H7 114.2 . . ? C3 C7 H7 114.2 . . ? C7 C8 C10 125.7(3) . . ? C7 C8 C9 118.6(3) . . ? C10 C8 C9 115.7(3) . . ? C17 C12 C13 118.0(3) . . ? C17 C12 C18 118.4(3) . . ? C13 C12 C18 123.5(3) . . ? N1 C10 C8 176.9(3) . . ? C14 C15 C16 117.7(3) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? C16 C17 C12 121.8(3) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? C18 C19 C21 125.4(3) . . ? C18 C19 C20 120.8(4) . . ? C21 C19 C20 113.7(3) . . ? C19 C18 C12 130.1(3) . . ? C19 C18 H18 115.0 . . ? C12 C18 H18 115.0 . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N2 C9 C8 178.1(4) . . ? N4 C20 C19 178.1(6) . . ? N5 C21 C19 178.7(5) . . ? 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 O7 C11 1.335(3) . ? O7 C1 1.408(3) . ? N3 C11 1.320(3) . ? N3 C11 1.327(3) 3_665 ? O22 C22 1.342(3) . ? O22 C14 1.409(3) . ? N6 C22 1.321(3) . ? N6 C22 1.324(3) 2_765 ? C11 N3 1.327(3) 2_655 ? C1 C6 1.363(4) . ? C1 C2 1.364(4) . ? C22 N6 1.324(3) 3_675 ? C3 C2 1.393(4) . ? C3 C4 1.394(4) . ? C3 C7 1.451(4) . ? C2 H2 0.9300 . ? C14 C15 1.359(4) . ? C14 C13 1.371(4) . ? C6 C5 1.380(4) . ? C6 H6 0.9300 . ? C4 C5 1.371(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C13 C12 1.394(4) . ? C13 H13 0.9300 . ? C7 C8 1.335(4) . ? C7 H7 0.9300 . ? C8 C10 1.428(5) . ? C8 C9 1.434(4) . ? C12 C17 1.371(5) . ? C12 C18 1.473(5) . ? C10 N1 1.142(5) . ? C15 C16 1.388(5) . ? C15 H15 0.9300 . ? C17 C16 1.374(5) . ? C17 H17 0.9300 . ? C19 C18 1.326(5) . ? C19 C21 1.401(6) . ? C19 C20 1.447(5) . ? C18 H18 0.9300 . ? C16 H16 0.9300 . ? N2 C9 1.141(4) . ? N4 C20 1.129(5) . ? C21 N5 1.142(7) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N3 C11 N3 -0.5(4) 3_665 . . 2_655 ? C11 N3 C11 O7 -179.67(11) 3_665 . . . ? C1 O7 C11 N3 -2.3(3) . . . . ? C1 O7 C11 N3 178.44(18) . . . 2_655 ? C11 O7 C1 C6 97.1(3) . . . . ? C11 O7 C1 C2 -87.6(3) . . . . ? C22 N6 C22 N6 1.1(4) 2_765 . . 3_675 ? C22 N6 C22 O22 179.29(12) 2_765 . . . ? C14 O22 C22 N6 8.9(3) . . . . ? C14 O22 C22 N6 -172.7(2) . . . 3_675 ? C6 C1 C2 C3 -0.2(4) . . . . ? O7 C1 C2 C3 -175.4(2) . . . . ? C4 C3 C2 C1 -0.5(4) . . . . ? C7 C3 C2 C1 178.6(2) . . . . ? C22 O22 C14 C15 -107.4(3) . . . . ? C22 O22 C14 C13 76.2(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? O7 C1 C6 C5 176.1(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C7 C3 C4 C5 -178.5(3) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C1 C6 C5 C4 -1.1(4) . . . . ? C15 C14 C13 C12 -0.1(5) . . . . ? O22 C14 C13 C12 176.2(3) . . . . ? C2 C3 C7 C8 -175.7(3) . . . . ? C4 C3 C7 C8 3.2(5) . . . . ? C3 C7 C8 C10 -2.6(6) . . . . ? C3 C7 C8 C9 176.9(3) . . . . ? C14 C13 C12 C17 0.6(4) . . . . ? C14 C13 C12 C18 177.9(3) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? O22 C14 C15 C16 -176.5(3) . . . . ? C13 C12 C17 C16 -0.8(5) . . . . ? C18 C12 C17 C16 -178.2(3) . . . . ? C21 C19 C18 C12 6.3(7) . . . . ? C20 C19 C18 C12 -174.7(3) . . . . ? C17 C12 C18 C19 -170.6(4) . . . . ? C13 C12 C18 C19 12.1(6) . . . . ? C12 C17 C16 C15 0.4(5) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ?