#------------------------------------------------------------------------------ #$Date: 2023-11-02 04:28:56 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287241 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247655.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_7247655 loop_ _publ_author_name 'Saito, Erika' 'Yamakado, Ryohei' 'Yasuhara, Taichi' 'Yamaguchi, Hiroto' 'Okada, Shuji' 'Yoshida, Tsukasa' _publ_section_title ; Formation of charge-transfer complexes in ionic crystals composed of 1,3-bis(dicyanomethylidene)indan anion and viologens bearing alkyl chains ; _journal_issue 45 _journal_name_full 'RSC Advances' _journal_page_first 32039 _journal_page_last 32044 _journal_paper_doi 10.1039/D3RA06782C _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C15 H5 N4, 0.5(C14 H18 N2)' _chemical_formula_sum 'C22 H14 N5' _chemical_formula_weight 348.38 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2023-06-09 deposited with the CCDC. 2023-10-26 downloaded from the CCDC. ; _cell_angle_alpha 73.506(2) _cell_angle_beta 71.656(3) _cell_angle_gamma 89.385(2) _cell_formula_units_Z 2 _cell_length_a 8.1502(3) _cell_length_b 10.8528(3) _cell_length_c 10.8895(3) _cell_measurement_reflns_used 7980 _cell_measurement_temperature 93 _cell_measurement_theta_max 30.4150 _cell_measurement_theta_min 1.9930 _cell_volume 873.36(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'Yadokari-XG (Wakita, Nemoto et al., 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXD (Sheldrick, 2015)' _diffrn_ambient_temperature 93 _diffrn_detector_area_resol_mean 'CCD plate' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0252 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11949 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_min 2.391 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dark yellow' _exptl_crystal_density_diffrn 1.325 _exptl_crystal_description platelet _exptl_crystal_F_000 362 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.329 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 247 _refine_ls_number_reflns 3969 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0426 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.2828P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1073 _refine_ls_wR_factor_ref 0.1153 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3375 _reflns_number_total 3969 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06782c2.cif _cod_data_source_block 20170411_EtV_-180 _cod_original_cell_volume 873.35(5) _cod_database_code 7247655 _shelx_shelxl_version_number 2014/7 _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 0.984 _shelx_estimated_absorpt_t_max 0.992 _oxdiff_exptl_absorpt_empirical_full_min 0.897 _oxdiff_exptl_absorpt_empirical_full_max 1.138 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _shelx_res_file ; 20170411-yoshidaLab2.res created by SHELXL-2014/7 TITL REM Yadorkari-X generated CELL 0.71073 8.1502 10.8528 10.8895 73.5056 71.6555 89.3852 ZERR 2.0 0.0003 0.0003 0.0003 0.0022 0.0026 0.0022 LATT 1 REM SPGR P-1 triclinic SFAC C H N UNIT 44 28 10 SIZE 0.20 0.15 0.10 TEMP -180.0 L.S. 50 FMAP 2 PLAN -20 ACTA CONF HTAB LIST 4 BOND $H OMIT -10.000000 55.000000 OMIT 1 0 0 OMIT 0 0 1 OMIT 1 0 1 OMIT 0 1 0 EQIV $1 +X, +Y, 1+Z EQIV $2 3-X, 2-Y, -Z EQIV $3 -1+X, +Y, +Z HTAB C16 N1_$1 HTAB C17 N3_$2 HTAB C19 N3_$3 HTAB C20 N4_$3 HTAB C16 N1_$1 HTAB C17 N3_$2 WGHT 0.061000 0.282800 FVAR 14.17868 C1 1 1.156479 0.748728 -0.085127 11.00000 0.01714 0.01853 = 0.01983 -0.00593 -0.00568 -0.00055 H1 2 1.243978 0.802699 -0.169065 11.00000 -1.20000 C2 1 0.994926 0.695474 -0.077175 11.00000 0.01721 0.01538 = 0.01941 -0.00613 -0.00583 0.00168 C3 1 0.906590 0.620415 0.066225 11.00000 0.01755 0.01560 = 0.01924 -0.00527 -0.00588 0.00165 C4 1 0.744694 0.552702 0.130520 11.00000 0.01887 0.01948 = 0.02433 -0.00680 -0.00738 -0.00016 AFIX 43 H4 2 0.668683 0.547485 0.081223 11.00000 -1.20000 AFIX 0 C5 1 0.695955 0.491907 0.270737 11.00000 0.01960 0.02199 = 0.02580 -0.00509 -0.00205 -0.00321 AFIX 43 H5 2 0.585184 0.445360 0.316674 11.00000 -1.20000 AFIX 0 C6 1 0.806526 0.498603 0.343261 11.00000 0.02578 0.02093 = 0.01856 -0.00309 -0.00365 -0.00039 AFIX 43 H6 2 0.771377 0.455770 0.437745 11.00000 -1.20000 AFIX 0 C7 1 0.970670 0.568467 0.277886 11.00000 0.02222 0.02098 = 0.01984 -0.00642 -0.00786 0.00254 AFIX 43 H7 2 1.046346 0.573703 0.327441 11.00000 -1.20000 AFIX 0 C8 1 1.019217 0.629201 0.140162 11.00000 0.01574 0.01663 = 0.02144 -0.00686 -0.00589 0.00124 C9 1 1.177937 0.710985 0.042707 11.00000 0.01618 0.01682 = 0.02070 -0.00746 -0.00566 0.00169 C10 1 0.930468 0.712114 -0.184434 11.00000 0.01842 0.01921 = 0.02084 -0.00597 -0.00803 0.00079 C11 1 1.029876 0.791320 -0.316377 11.00000 0.02320 0.02209 = 0.02401 -0.00853 -0.01223 0.00190 C12 1 0.772291 0.649186 -0.175273 11.00000 0.02356 0.02091 = 0.02210 -0.00590 -0.01109 0.00283 C13 1 1.320514 0.748503 0.073088 11.00000 0.01650 0.02317 = 0.01971 -0.00759 -0.00574 0.00100 C14 1 1.458410 0.834415 -0.030971 11.00000 0.01741 0.02596 = 0.02522 -0.01162 -0.01044 0.00168 C15 1 1.335198 0.712281 0.205337 11.00000 0.01751 0.02877 = 0.02579 -0.00930 -0.00797 -0.00076 C16 1 0.971052 0.894306 0.301150 11.00000 0.01803 0.02059 = 0.01974 -0.00624 -0.00822 0.00089 AFIX 43 H16 2 1.032163 0.890985 0.363142 11.00000 -1.20000 AFIX 0 C17 1 1.048483 0.959542 0.165687 11.00000 0.01678 0.01887 = 0.01961 -0.00560 -0.00643 -0.00016 AFIX 43 H17 2 1.162441 1.000689 0.135000 11.00000 -1.20000 AFIX 0 C18 1 0.959637 0.965266 0.073384 11.00000 0.01754 0.01531 = 0.01744 -0.00482 -0.00585 0.00153 C19 1 0.792183 0.902679 0.124039 11.00000 0.01911 0.02342 = 0.02005 -0.00532 -0.00994 -0.00013 AFIX 43 H19 2 0.728004 0.904270 0.064424 11.00000 -1.20000 AFIX 0 C20 1 0.720292 0.838808 0.260105 11.00000 0.01807 0.02422 = 0.02148 -0.00488 -0.00702 -0.00196 AFIX 43 H20 2 0.606531 0.796781 0.293570 11.00000 -1.20000 AFIX 0 C21 1 0.725741 0.765470 0.492941 11.00000 0.02267 0.02395 = 0.01612 -0.00144 -0.00459 -0.00137 AFIX 23 H21 2 0.815891 0.747089 0.537412 11.00000 -1.20000 H21A 2 0.667477 0.682090 0.502455 11.00000 -1.20000 AFIX 0 C22 1 0.594274 0.844240 0.562272 11.00000 0.03413 0.03134 = 0.02148 -0.00529 -0.00200 0.00521 AFIX 33 H22 2 0.541547 0.796290 0.658210 11.00000 -1.50000 H22A 2 0.652167 0.926207 0.554230 11.00000 -1.50000 H22B 2 0.503904 0.861274 0.519309 11.00000 -1.50000 AFIX 0 N1 3 1.108544 0.856715 -0.422775 11.00000 0.03229 0.03125 = 0.02285 -0.00387 -0.01016 -0.00295 N2 3 0.647722 0.598815 -0.173806 11.00000 0.02614 0.02923 = 0.03056 -0.00658 -0.01477 -0.00152 N3 3 1.566566 0.905958 -0.115412 11.00000 0.02183 0.03341 = 0.02874 -0.00917 -0.00771 -0.00517 N4 3 1.348277 0.686293 0.311874 11.00000 0.02505 0.04491 = 0.02426 -0.00676 -0.00983 -0.00537 N5 3 0.809255 0.835181 0.346329 11.00000 0.01931 0.01916 = 0.01711 -0.00429 -0.00551 0.00056 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0426 for 3375 Fo > 4sig(Fo) and 0.0508 for all 3969 data REM 247 parameters refined using 0 restraints END WGHT 0.0610 0.2840 REM Instructions for potential hydrogen bonds HTAB C16 N1_$1 HTAB C17 N3_$2 HTAB C19 N3_$3 HTAB C20 N4_$3 REM Highest difference peak 0.329, deepest hole -0.231, 1-sigma level 0.045 Q1 1 0.9424 0.6533 -0.0075 11.00000 0.05 0.33 Q2 1 0.9622 0.6185 0.1042 11.00000 0.05 0.32 Q3 1 1.0000 1.0000 0.0000 10.50000 0.05 0.29 Q4 1 1.1063 0.6643 0.1005 11.00000 0.05 0.28 Q5 1 1.0869 0.7222 -0.0906 11.00000 0.05 0.28 Q6 1 0.9966 0.9365 0.2335 11.00000 0.05 0.26 Q7 1 0.8665 0.9514 0.1007 11.00000 0.05 0.26 Q8 1 1.0040 0.9630 0.1197 11.00000 0.05 0.25 Q9 1 0.7121 0.5346 0.2066 11.00000 0.05 0.24 Q10 1 0.7665 0.8785 0.1878 11.00000 0.05 0.24 Q11 1 1.1575 0.7683 -0.0182 11.00000 0.05 0.24 Q12 1 1.3907 0.8003 0.0220 11.00000 0.05 0.23 Q13 1 1.0069 0.5846 0.2073 11.00000 0.05 0.23 Q14 1 0.8162 0.5951 0.0990 11.00000 0.05 0.22 Q15 1 0.9750 0.6948 -0.1352 11.00000 0.05 0.22 Q16 1 0.6786 0.8194 0.5204 11.00000 0.05 0.21 Q17 1 0.8959 0.5203 0.2978 11.00000 0.05 0.21 Q18 1 0.7676 0.8019 0.4190 11.00000 0.05 0.20 Q19 1 1.2292 0.7490 0.0645 11.00000 0.05 0.20 Q20 1 0.9500 0.7193 -0.1251 11.00000 0.05 0.19 ; _shelx_res_checksum 76465 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.15648(15) 0.74873(11) -0.08513(12) 0.0185(2) Uani 1 1 d . . . . . H1 H 1.2440(19) 0.8027(14) -0.1691(15) 0.022 Uiso 1 1 d . U . . . C2 C 0.99493(15) 0.69547(11) -0.07717(12) 0.0172(2) Uani 1 1 d . . . . . C3 C 0.90659(15) 0.62041(11) 0.06622(12) 0.0175(2) Uani 1 1 d . . . . . C4 C 0.74469(16) 0.55270(11) 0.13052(12) 0.0207(3) Uani 1 1 d . . . . . H4 H 0.6687 0.5475 0.0812 0.025 Uiso 1 1 calc R U . . . C5 C 0.69595(16) 0.49191(12) 0.27074(13) 0.0242(3) Uani 1 1 d . . . . . H5 H 0.5852 0.4454 0.3167 0.029 Uiso 1 1 calc R U . . . C6 C 0.80653(17) 0.49860(12) 0.34326(13) 0.0232(3) Uani 1 1 d . . . . . H6 H 0.7714 0.4558 0.4377 0.028 Uiso 1 1 calc R U . . . C7 C 0.97067(16) 0.56847(11) 0.27789(12) 0.0207(3) Uani 1 1 d . . . . . H7 H 1.0463 0.5737 0.3274 0.025 Uiso 1 1 calc R U . . . C8 C 1.01922(15) 0.62920(11) 0.14016(12) 0.0177(2) Uani 1 1 d . . . . . C9 C 1.17794(15) 0.71099(11) 0.04271(12) 0.0176(2) Uani 1 1 d . . . . . C10 C 0.93047(15) 0.71211(11) -0.18443(12) 0.0191(2) Uani 1 1 d . . . . . C11 C 1.02988(16) 0.79132(12) -0.31638(13) 0.0216(3) Uani 1 1 d . . . . . C12 C 0.77229(16) 0.64919(12) -0.17527(12) 0.0214(3) Uani 1 1 d . . . . . C13 C 1.32051(15) 0.74850(12) 0.07309(12) 0.0196(3) Uani 1 1 d . . . . . C14 C 1.45841(15) 0.83441(12) -0.03097(13) 0.0211(3) Uani 1 1 d . . . . . C15 C 1.33520(16) 0.71228(12) 0.20534(13) 0.0235(3) Uani 1 1 d . . . . . C16 C 0.97105(15) 0.89431(11) 0.30115(12) 0.0189(2) Uani 1 1 d . . . . . H16 H 1.0322 0.8910 0.3631 0.023 Uiso 1 1 calc R U . . . C17 C 1.04848(15) 0.95954(11) 0.16569(12) 0.0183(2) Uani 1 1 d . . . . . H17 H 1.1624 1.0007 0.1350 0.022 Uiso 1 1 calc R U . . . C18 C 0.95964(15) 0.96527(11) 0.07338(11) 0.0167(2) Uani 1 1 d . . . . . C19 C 0.79218(16) 0.90268(12) 0.12404(12) 0.0202(3) Uani 1 1 d . . . . . H19 H 0.7280 0.9043 0.0644 0.024 Uiso 1 1 calc R U . . . C20 C 0.72029(16) 0.83881(12) 0.26010(12) 0.0215(3) Uani 1 1 d . . . . . H20 H 0.6065 0.7968 0.2936 0.026 Uiso 1 1 calc R U . . . C21 C 0.72574(16) 0.76547(12) 0.49294(12) 0.0223(3) Uani 1 1 d . . . . . H21 H 0.8159 0.7471 0.5374 0.027 Uiso 1 1 calc R U . . . H21A H 0.6675 0.6821 0.5025 0.027 Uiso 1 1 calc R U . . . C22 C 0.59427(19) 0.84424(14) 0.56227(13) 0.0313(3) Uani 1 1 d . . . . . H22 H 0.5415 0.7963 0.6582 0.047 Uiso 1 1 calc R U . . . H22A H 0.6522 0.9262 0.5542 0.047 Uiso 1 1 calc R U . . . H22B H 0.5039 0.8613 0.5193 0.047 Uiso 1 1 calc R U . . . N1 N 1.10854(15) 0.85672(11) -0.42277(11) 0.0294(3) Uani 1 1 d . . . . . N2 N 0.64772(15) 0.59882(11) -0.17381(12) 0.0277(3) Uani 1 1 d . . . . . N3 N 1.56657(14) 0.90596(11) -0.11541(12) 0.0281(3) Uani 1 1 d . . . . . N4 N 1.34828(15) 0.68629(13) 0.31187(12) 0.0317(3) Uani 1 1 d . . . . . N5 N 0.80926(13) 0.83518(10) 0.34633(10) 0.0189(2) 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 C1 0.0171(6) 0.0185(5) 0.0198(6) -0.0059(5) -0.0057(5) -0.0006(4) C2 0.0172(5) 0.0154(5) 0.0194(6) -0.0061(4) -0.0058(4) 0.0017(4) C3 0.0176(6) 0.0156(5) 0.0192(5) -0.0053(4) -0.0059(4) 0.0016(4) C4 0.0189(6) 0.0195(6) 0.0243(6) -0.0068(5) -0.0074(5) -0.0002(5) C5 0.0196(6) 0.0220(6) 0.0258(6) -0.0051(5) -0.0021(5) -0.0032(5) C6 0.0258(6) 0.0209(6) 0.0186(6) -0.0031(5) -0.0037(5) -0.0004(5) C7 0.0222(6) 0.0210(6) 0.0198(6) -0.0064(5) -0.0079(5) 0.0025(5) C8 0.0157(5) 0.0166(5) 0.0214(6) -0.0069(4) -0.0059(5) 0.0012(4) C9 0.0162(6) 0.0168(5) 0.0207(6) -0.0075(4) -0.0057(4) 0.0017(4) C10 0.0184(6) 0.0192(6) 0.0208(6) -0.0060(5) -0.0080(5) 0.0008(4) C11 0.0232(6) 0.0221(6) 0.0240(6) -0.0085(5) -0.0122(5) 0.0019(5) C12 0.0236(6) 0.0209(6) 0.0221(6) -0.0059(5) -0.0111(5) 0.0028(5) C13 0.0165(6) 0.0232(6) 0.0197(6) -0.0076(5) -0.0057(5) 0.0010(4) C14 0.0174(6) 0.0260(6) 0.0252(6) -0.0116(5) -0.0104(5) 0.0017(5) C15 0.0175(6) 0.0288(6) 0.0258(7) -0.0093(5) -0.0080(5) -0.0008(5) C16 0.0180(6) 0.0206(6) 0.0197(6) -0.0062(5) -0.0082(5) 0.0009(4) C17 0.0168(5) 0.0189(5) 0.0196(6) -0.0056(4) -0.0064(5) -0.0002(4) C18 0.0175(6) 0.0153(5) 0.0174(6) -0.0048(4) -0.0058(5) 0.0015(4) C19 0.0191(6) 0.0234(6) 0.0201(6) -0.0053(5) -0.0099(5) -0.0001(5) C20 0.0181(6) 0.0242(6) 0.0215(6) -0.0049(5) -0.0070(5) -0.0020(5) C21 0.0227(6) 0.0239(6) 0.0161(6) -0.0014(5) -0.0046(5) -0.0014(5) C22 0.0341(8) 0.0313(7) 0.0215(6) -0.0053(5) -0.0020(5) 0.0052(6) N1 0.0323(6) 0.0313(6) 0.0229(6) -0.0039(5) -0.0102(5) -0.0030(5) N2 0.0261(6) 0.0292(6) 0.0306(6) -0.0066(5) -0.0148(5) -0.0015(5) N3 0.0218(6) 0.0334(6) 0.0287(6) -0.0092(5) -0.0077(5) -0.0052(5) N4 0.0251(6) 0.0449(7) 0.0243(6) -0.0068(5) -0.0098(5) -0.0054(5) N5 0.0193(5) 0.0192(5) 0.0171(5) -0.0043(4) -0.0055(4) 0.0006(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 C9 C1 C2 110.08(10) . . ? C9 C1 H1 124.7(8) . . ? C2 C1 H1 125.2(8) . . ? C10 C2 C1 125.94(11) . . ? C10 C2 C3 126.64(11) . . ? C1 C2 C3 107.42(10) . . ? C4 C3 C8 120.86(11) . . ? C4 C3 C2 131.58(11) . . ? C8 C3 C2 107.55(10) . . ? C3 C4 C5 118.17(11) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 121.24(11) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.52(11) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 118.61(11) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C3 120.59(11) . . ? C7 C8 C9 132.23(11) . . ? C3 C8 C9 107.18(10) . . ? C13 C9 C1 125.67(11) . . ? C13 C9 C8 126.52(11) . . ? C1 C9 C8 107.76(10) . . ? C2 C10 C12 124.59(11) . . ? C2 C10 C11 119.71(11) . . ? C12 C10 C11 115.61(11) . . ? N1 C11 C10 178.99(14) . . ? N2 C12 C10 177.00(13) . . ? C9 C13 C15 124.22(11) . . ? C9 C13 C14 119.63(11) . . ? C15 C13 C14 116.06(11) . . ? N3 C14 C13 178.24(14) . . ? N4 C15 C13 178.21(14) . . ? N5 C16 C17 120.60(11) . . ? N5 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.23(11) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C19 117.51(11) . . ? C17 C18 C18 121.31(13) . 2_775 ? C19 C18 C18 121.18(13) . 2_775 ? C20 C19 C18 120.17(11) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? N5 C20 C19 120.85(11) . . ? N5 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? N5 C21 C22 111.19(10) . . ? N5 C21 H21 109.4 . . ? C22 C21 H21 109.4 . . ? N5 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? H21 C21 H21A 108.0 . . ? C21 C22 H22 109.5 . . ? C21 C22 H22A 109.5 . . ? H22 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 N5 C16 120.64(10) . . ? C20 N5 C21 118.96(10) . . ? C16 N5 C21 120.40(10) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.4015(16) . ? C1 C2 1.4111(16) . ? C1 H1 0.991(15) . ? C2 C10 1.3919(16) . ? C2 C3 1.4842(16) . ? C3 C4 1.3851(16) . ? C3 C8 1.4180(16) . ? C4 C5 1.4058(17) . ? C4 H4 0.9500 . ? C5 C6 1.3867(19) . ? C5 H5 0.9500 . ? C6 C7 1.4097(17) . ? C6 H6 0.9500 . ? C7 C8 1.3824(17) . ? C7 H7 0.9500 . ? C8 C9 1.4876(16) . ? C9 C13 1.3979(16) . ? C10 C12 1.4274(17) . ? C10 C11 1.4285(17) . ? C11 N1 1.1543(17) . ? C12 N2 1.1518(17) . ? C13 C15 1.4244(17) . ? C13 C14 1.4274(17) . ? C14 N3 1.1509(17) . ? C15 N4 1.1525(17) . ? C16 N5 1.3503(15) . ? C16 C17 1.3806(16) . ? C16 H16 0.9500 . ? C17 C18 1.4001(17) . ? C17 H17 0.9500 . ? C18 C19 1.4005(17) . ? C18 C18 1.490(2) 2_775 ? C19 C20 1.3778(17) . ? C19 H19 0.9500 . ? C20 N5 1.3475(16) . ? C20 H20 0.9500 . ? C21 N5 1.4919(15) . ? C21 C22 1.5121(18) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 H22 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C16 H16 N1 0.95 2.53 3.4459(16) 163.3 1_556 C17 H17 N3 0.95 2.36 3.2920(16) 166.1 2_875 C19 H19 N3 0.95 2.68 3.6257(17) 176.2 1_455 C20 H20 N4 0.95 2.36 3.2791(17) 163.1 1_455 C16 H16 N1 0.95 2.53 3.4459(16) 163.3 1_556 C17 H17 N3 0.95 2.36 3.2920(16) 166.1 2_875 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 C9 C1 C2 C10 -179.75(11) . . . . ? C9 C1 C2 C3 0.95(13) . . . . ? C10 C2 C3 C4 -1.6(2) . . . . ? C1 C2 C3 C4 177.68(12) . . . . ? C10 C2 C3 C8 179.84(11) . . . . ? C1 C2 C3 C8 -0.87(12) . . . . ? C8 C3 C4 C5 -0.64(17) . . . . ? C2 C3 C4 C5 -179.03(11) . . . . ? C3 C4 C5 C6 -0.30(18) . . . . ? C4 C5 C6 C7 0.84(19) . . . . ? C5 C6 C7 C8 -0.43(18) . . . . ? C6 C7 C8 C3 -0.49(17) . . . . ? C6 C7 C8 C9 178.64(11) . . . . ? C4 C3 C8 C7 1.04(17) . . . . ? C2 C3 C8 C7 179.78(10) . . . . ? C4 C3 C8 C9 -178.28(10) . . . . ? C2 C3 C8 C9 0.46(12) . . . . ? C2 C1 C9 C13 -178.26(11) . . . . ? C2 C1 C9 C8 -0.68(13) . . . . ? C7 C8 C9 C13 -1.5(2) . . . . ? C3 C8 C9 C13 177.67(11) . . . . ? C7 C8 C9 C1 -179.10(12) . . . . ? C3 C8 C9 C1 0.11(12) . . . . ? C1 C2 C10 C12 175.07(11) . . . . ? C3 C2 C10 C12 -5.77(19) . . . . ? C1 C2 C10 C11 -1.29(18) . . . . ? C3 C2 C10 C11 177.88(11) . . . . ? C1 C9 C13 C15 177.48(12) . . . . ? C8 C9 C13 C15 0.34(19) . . . . ? C1 C9 C13 C14 1.18(18) . . . . ? C8 C9 C13 C14 -175.96(11) . . . . ? N5 C16 C17 C18 0.09(18) . . . . ? C16 C17 C18 C19 -0.15(17) . . . . ? C16 C17 C18 C18 -179.84(12) . . . 2_775 ? C17 C18 C19 C20 0.17(17) . . . . ? C18 C18 C19 C20 179.86(13) 2_775 . . . ? C18 C19 C20 N5 -0.13(19) . . . . ? C19 C20 N5 C16 0.07(18) . . . . ? C19 C20 N5 C21 179.66(11) . . . . ? C17 C16 N5 C20 -0.05(17) . . . . ? C17 C16 N5 C21 -179.64(10) . . . . ? C22 C21 N5 C20 -76.92(14) . . . . ? C22 C21 N5 C16 102.67(13) . . . . ?