#------------------------------------------------------------------------------ #$Date: 2023-11-02 04:28:56 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287241 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247653.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_7247653 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(C12 H14 N2)' _chemical_formula_sum 'C21 H12 N5' _chemical_formula_weight 334.36 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-06-09 deposited with the CCDC. 2023-10-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.012(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.3110(4) _cell_length_b 19.5847(4) _cell_length_c 11.1122(3) _cell_measurement_reflns_used 15886 _cell_measurement_temperature 93 _cell_measurement_theta_max 31.1550 _cell_measurement_theta_min 2.6230 _cell_volume 3375.78(15) _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-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 93 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_unetI/netI 0.0198 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 27672 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_min 2.226 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Brown _exptl_crystal_density_diffrn 1.316 _exptl_crystal_description block _exptl_crystal_F_000 1384 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.300 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 3873 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0401 _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^)+(0.0639P)^2^+1.6845P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1058 _refine_ls_wR_factor_ref 0.1115 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3417 _reflns_number_total 3873 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06782c2.cif _cod_data_source_block 160807_MeV_-180 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7247653 _shelx_shelxl_version_number 2018/3 _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 0.989 _shelx_estimated_absorpt_t_max 0.993 _oxdiff_exptl_absorpt_empirical_full_min 0.736 _oxdiff_exptl_absorpt_empirical_full_max 1.337 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _shelx_res_file ; TITL 160807_Yoshida_2_a.res in C2/c 160807_Yoshida_2.res created by SHELXL-2018/3 at 14:48:17 on 20-Mar-2019 REM Yadorkari-X generated CELL 0.71073 16.3110 19.5847 11.1122 90.0000 108.0120 90.0000 ZERR 8.0 0.0004 0.0004 0.0003 0.0000 0.0030 0.0000 LATT 7 SYMM -X, +Y, 1/2-Z REM SPGR C2/c monoclinic SFAC C H N UNIT 168 96 40 SIZE 0.13 0.13 0.08 TEMP -180.0 L.S. 40 FMAP 2 PLAN -20 ACTA CONF LIST 4 BOND $H OMIT -10.000000 55.000000 OMIT 1 1 1 OMIT 2 0 0 WGHT 0.063900 1.684500 FVAR 2.86807 C1 1 0.328727 0.278224 0.391925 11.00000 0.01490 0.02002 = 0.02096 -0.00438 0.00579 -0.00127 C2 1 0.360443 0.283537 0.523566 11.00000 0.01867 0.01889 = 0.01961 -0.00221 0.00513 -0.00157 H2 2 0.374840 0.326147 0.569104 11.00000 -1.20000 C3 1 0.368009 0.218547 0.579504 11.00000 0.01534 0.01942 = 0.02192 -0.00259 0.00665 -0.00063 C4 1 0.333169 0.097315 0.476833 11.00000 0.02797 0.01980 = 0.02977 -0.00249 0.00851 0.00103 AFIX 43 H4 2 0.349845 0.072723 0.554320 11.00000 -1.20000 AFIX 0 C5 1 0.300816 0.062971 0.360198 11.00000 0.03452 0.01976 = 0.03705 -0.00835 0.00931 -0.00095 AFIX 43 H5 2 0.295492 0.014651 0.358883 11.00000 -1.20000 AFIX 0 C6 1 0.276792 0.098997 0.247807 11.00000 0.03105 0.02578 = 0.02973 -0.01233 0.00689 -0.00220 AFIX 43 H6 2 0.255037 0.074976 0.170152 11.00000 -1.20000 AFIX 0 C7 1 0.283909 0.170555 0.246080 11.00000 0.02298 0.02492 = 0.02348 -0.00604 0.00633 -0.00046 AFIX 43 H7 2 0.267522 0.195014 0.168447 11.00000 -1.20000 AFIX 0 C8 1 0.315416 0.204349 0.360485 11.00000 0.01673 0.02011 = 0.02154 -0.00446 0.00614 -0.00059 C9 1 0.340020 0.167537 0.475687 11.00000 0.01830 0.01973 = 0.02261 -0.00451 0.00705 -0.00033 C10 1 0.312750 0.333223 0.307250 11.00000 0.01880 0.02125 = 0.01758 -0.00245 0.00488 -0.00113 C11 1 0.274351 0.327915 0.174002 11.00000 0.02192 0.02363 = 0.02178 -0.00201 0.00670 0.00044 N1 3 0.243230 0.326203 0.065777 11.00000 0.03617 0.03365 = 0.02125 -0.00291 0.00510 0.00233 C12 1 0.332748 0.400652 0.355613 11.00000 0.02139 0.02358 = 0.01717 0.00116 0.00458 0.00099 N2 3 0.351690 0.454465 0.397259 11.00000 0.03532 0.02287 = 0.02447 -0.00083 0.00527 -0.00097 C13 1 0.394925 0.205819 0.708948 11.00000 0.01903 0.01784 = 0.02137 -0.00081 0.00622 -0.00021 C14 1 0.403682 0.140300 0.767336 11.00000 0.02244 0.02220 = 0.02519 -0.00151 0.00991 0.00079 N3 3 0.412167 0.088987 0.820782 11.00000 0.03867 0.02359 = 0.03563 0.00425 0.01637 0.00380 C15 1 0.414420 0.262283 0.794168 11.00000 0.01953 0.02230 = 0.01721 0.00262 0.00578 0.00056 N4 3 0.429251 0.308491 0.861587 11.00000 0.02890 0.02572 = 0.01918 -0.00040 0.00664 -0.00009 N5 3 0.500000 0.517068 0.750000 10.50000 0.03928 0.01436 = 0.02787 0.00000 0.00724 0.00000 C16 1 0.541508 0.550955 0.856865 11.00000 0.03155 0.01914 = 0.02101 0.00364 0.00576 0.00239 AFIX 43 H16 2 0.570798 0.526153 0.931203 11.00000 -1.20000 AFIX 0 C17 1 0.541892 0.621104 0.859393 11.00000 0.02482 0.01815 = 0.01728 0.00007 0.00536 0.00065 AFIX 43 H17 2 0.570688 0.644505 0.935647 11.00000 -1.20000 AFIX 0 C18 1 0.500000 0.658181 0.750000 10.50000 0.01944 0.01452 = 0.01712 0.00000 0.00769 0.00000 C19 1 0.500000 0.734132 0.750000 10.50000 0.01926 0.01533 = 0.02007 0.00000 0.00841 0.00000 C20 1 0.544875 0.771054 0.857242 11.00000 0.03814 0.01854 = 0.02139 0.00002 0.00216 -0.00332 AFIX 43 H20 2 0.576572 0.747635 0.932024 11.00000 -1.20000 AFIX 0 C21 1 0.543514 0.841320 0.855382 11.00000 0.03938 0.02004 = 0.02916 -0.00406 0.00461 -0.00454 AFIX 43 H21 2 0.573684 0.865985 0.929452 11.00000 -1.20000 AFIX 0 N6 3 0.500000 0.875499 0.750000 10.50000 0.02583 0.01495 = 0.03656 0.00000 0.01100 0.00000 C22 1 0.500000 0.441685 0.750000 10.50000 0.10539 0.01169 = 0.05024 0.00000 -0.00953 0.00000 AFIX 33 H22 2 0.467251 0.425005 0.665683 10.50000 -1.50000 H22A 2 0.559463 0.425005 0.772125 10.50000 -1.50000 H22B 2 0.473286 0.425005 0.812192 10.50000 -1.50000 AFIX 0 C23 1 0.500000 0.951243 0.750000 10.50000 0.04081 0.01352 = 0.05688 0.00000 0.01033 0.00000 AFIX 33 H23 2 0.465538 0.967922 0.666540 10.50000 -1.50000 H23A 2 0.475156 0.967923 0.814294 10.50000 -1.50000 H23B 2 0.559306 0.967923 0.769166 10.50000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 160807_Yoshida_2_a.res in C2/c REM wR2 = 0.1115, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0401 for 3417 Fo > 4sig(Fo) and 0.0462 for all 3873 data REM 241 parameters refined using 0 restraints END WGHT 0.0639 1.6845 REM Highest difference peak 0.300, deepest hole -0.198, 1-sigma level 0.042 Q1 1 0.5000 0.6930 0.7500 10.50000 0.05 0.30 Q2 1 0.5092 0.6395 0.8080 11.00000 0.05 0.28 Q3 1 0.4871 0.4218 0.6699 11.00000 0.05 0.26 Q4 1 0.3588 0.2544 0.5568 11.00000 0.05 0.26 Q5 1 0.3282 0.1833 0.4135 11.00000 0.05 0.25 Q6 1 0.5513 0.5885 0.8455 11.00000 0.05 0.24 Q7 1 0.4645 0.9688 0.5491 11.00000 0.05 0.23 Q8 1 0.3203 0.2448 0.3632 11.00000 0.05 0.23 Q9 1 0.3649 0.2852 0.4585 11.00000 0.05 0.23 Q10 1 0.5300 0.7515 0.7975 11.00000 0.05 0.23 Q11 1 0.3528 0.1912 0.5332 11.00000 0.05 0.22 Q12 1 0.4963 0.8604 0.8221 11.00000 0.05 0.21 Q13 1 0.3030 0.1902 0.3131 11.00000 0.05 0.20 Q14 1 0.2854 0.3245 0.2424 11.00000 0.05 0.20 Q15 1 0.3391 0.3061 0.3407 11.00000 0.05 0.20 Q16 1 0.3297 0.3663 0.3249 11.00000 0.05 0.19 Q17 1 0.4044 0.2307 0.7441 11.00000 0.05 0.19 Q18 1 0.5403 0.8564 0.7896 11.00000 0.05 0.19 Q19 1 0.3265 0.1363 0.4794 11.00000 0.05 0.19 Q20 1 0.2638 0.0833 0.3048 11.00000 0.05 0.19 ; _shelx_res_checksum 53953 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 0.32873(6) 0.27822(5) 0.39192(9) 0.0186(2) Uani 1 1 d . . . . . C2 C 0.36044(6) 0.28354(5) 0.52357(9) 0.0192(2) Uani 1 1 d . . . . . H2 H 0.3748(8) 0.3261(7) 0.5691(12) 0.023 Uiso 1 1 d . U . . . C3 C 0.36801(6) 0.21855(5) 0.57950(9) 0.0187(2) Uani 1 1 d . . . . . C4 C 0.33317(7) 0.09731(6) 0.47683(11) 0.0259(2) Uani 1 1 d . . . . . H4 H 0.349845 0.072723 0.554320 0.031 Uiso 1 1 calc R U . . . C5 C 0.30082(8) 0.06297(6) 0.36020(12) 0.0308(3) Uani 1 1 d . . . . . H5 H 0.295492 0.014651 0.358883 0.037 Uiso 1 1 calc R U . . . C6 C 0.27679(7) 0.09900(6) 0.24781(11) 0.0294(3) Uani 1 1 d . . . . . H6 H 0.255037 0.074976 0.170152 0.035 Uiso 1 1 calc R U . . . C7 C 0.28391(7) 0.17056(6) 0.24608(10) 0.0240(2) Uani 1 1 d . . . . . H7 H 0.267522 0.195014 0.168447 0.029 Uiso 1 1 calc R U . . . C8 C 0.31542(6) 0.20435(5) 0.36048(10) 0.0194(2) Uani 1 1 d . . . . . C9 C 0.34002(6) 0.16754(5) 0.47569(10) 0.0201(2) Uani 1 1 d . . . . . C10 C 0.31275(6) 0.33322(5) 0.30725(9) 0.0194(2) Uani 1 1 d . . . . . C11 C 0.27435(7) 0.32791(5) 0.17400(10) 0.0225(2) Uani 1 1 d . . . . . N1 N 0.24323(7) 0.32620(5) 0.06578(9) 0.0312(2) Uani 1 1 d . . . . . C12 C 0.33275(7) 0.40065(5) 0.35561(9) 0.0210(2) Uani 1 1 d . . . . . N2 N 0.35169(7) 0.45446(5) 0.39726(9) 0.0285(2) Uani 1 1 d . . . . . C13 C 0.39493(6) 0.20582(5) 0.70895(10) 0.0194(2) Uani 1 1 d . . . . . C14 C 0.40368(7) 0.14030(5) 0.76734(10) 0.0227(2) Uani 1 1 d . . . . . N3 N 0.41217(7) 0.08899(5) 0.82078(10) 0.0315(2) Uani 1 1 d . . . . . C15 C 0.41442(6) 0.26228(5) 0.79417(9) 0.0197(2) Uani 1 1 d . . . . . N4 N 0.42925(6) 0.30849(5) 0.86159(8) 0.0248(2) Uani 1 1 d . . . . . N5 N 0.500000 0.51707(6) 0.750000 0.0279(3) Uani 1 2 d S T P . . C16 C 0.54151(7) 0.55096(6) 0.85687(10) 0.0244(2) Uani 1 1 d . . . . . H16 H 0.570798 0.526153 0.931203 0.029 Uiso 1 1 calc R U . . . C17 C 0.54189(7) 0.62110(5) 0.85939(9) 0.0203(2) Uani 1 1 d . . . . . H17 H 0.570688 0.644505 0.935647 0.024 Uiso 1 1 calc R U . . . C18 C 0.500000 0.65818(7) 0.750000 0.0166(3) Uani 1 2 d S T P . . C19 C 0.500000 0.73413(7) 0.750000 0.0177(3) Uani 1 2 d S T P . . C20 C 0.54488(8) 0.77105(6) 0.85724(10) 0.0276(3) Uani 1 1 d . . . . . H20 H 0.576572 0.747635 0.932024 0.033 Uiso 1 1 calc R U . . . C21 C 0.54351(8) 0.84132(6) 0.85538(11) 0.0309(3) Uani 1 1 d . . . . . H21 H 0.573684 0.865985 0.929452 0.037 Uiso 1 1 calc R U . . . N6 N 0.500000 0.87550(6) 0.750000 0.0255(3) Uani 1 2 d S T P . . C22 C 0.500000 0.44168(9) 0.750000 0.0634(8) Uani 1 2 d S T P . . H22 H 0.467251 0.425005 0.665683 0.095 Uiso 0.5 1 calc R U P . . H22A H 0.559463 0.425005 0.772125 0.095 Uiso 0.5 1 calc R U P . . H22B H 0.473286 0.425005 0.812192 0.095 Uiso 0.5 1 calc R U P . . C23 C 0.500000 0.95124(8) 0.750000 0.0382(4) Uani 1 2 d S T P . . H23 H 0.465538 0.967922 0.666540 0.057 Uiso 0.5 1 calc R U P . . H23A H 0.475156 0.967923 0.814294 0.057 Uiso 0.5 1 calc R U P . . H23B H 0.559306 0.967923 0.769166 0.057 Uiso 0.5 1 calc R U P . . 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 0.0149(4) 0.0200(5) 0.0210(5) -0.0044(4) 0.0058(4) -0.0013(4) C2 0.0187(5) 0.0189(5) 0.0196(5) -0.0022(4) 0.0051(4) -0.0016(4) C3 0.0153(4) 0.0194(5) 0.0219(5) -0.0026(4) 0.0066(4) -0.0006(4) C4 0.0280(5) 0.0198(5) 0.0298(6) -0.0025(4) 0.0085(5) 0.0010(4) C5 0.0345(6) 0.0198(5) 0.0371(7) -0.0084(5) 0.0093(5) -0.0010(4) C6 0.0311(6) 0.0258(6) 0.0297(6) -0.0123(4) 0.0069(5) -0.0022(4) C7 0.0230(5) 0.0249(6) 0.0235(5) -0.0060(4) 0.0063(4) -0.0005(4) C8 0.0167(4) 0.0201(5) 0.0215(5) -0.0045(4) 0.0061(4) -0.0006(4) C9 0.0183(5) 0.0197(5) 0.0226(5) -0.0045(4) 0.0071(4) -0.0003(4) C10 0.0188(5) 0.0212(5) 0.0176(5) -0.0025(4) 0.0049(4) -0.0011(4) C11 0.0219(5) 0.0236(5) 0.0218(5) -0.0020(4) 0.0067(4) 0.0004(4) N1 0.0362(5) 0.0336(5) 0.0213(5) -0.0029(4) 0.0051(4) 0.0023(4) C12 0.0214(5) 0.0236(5) 0.0172(5) 0.0012(4) 0.0046(4) 0.0010(4) N2 0.0353(5) 0.0229(5) 0.0245(5) -0.0008(4) 0.0053(4) -0.0010(4) C13 0.0190(5) 0.0178(5) 0.0214(5) -0.0008(4) 0.0062(4) -0.0002(4) C14 0.0224(5) 0.0222(5) 0.0252(5) -0.0015(4) 0.0099(4) 0.0008(4) N3 0.0387(6) 0.0236(5) 0.0356(6) 0.0042(4) 0.0164(5) 0.0038(4) C15 0.0195(5) 0.0223(5) 0.0172(5) 0.0026(4) 0.0058(4) 0.0006(4) N4 0.0289(5) 0.0257(5) 0.0192(4) -0.0004(3) 0.0066(4) -0.0001(4) N5 0.0393(8) 0.0144(6) 0.0279(7) 0.000 0.0072(6) 0.000 C16 0.0315(6) 0.0191(5) 0.0210(5) 0.0036(4) 0.0058(4) 0.0024(4) C17 0.0248(5) 0.0181(5) 0.0173(5) 0.0001(4) 0.0054(4) 0.0006(4) C18 0.0194(6) 0.0145(6) 0.0171(6) 0.000 0.0077(5) 0.000 C19 0.0193(6) 0.0153(6) 0.0201(7) 0.000 0.0084(5) 0.000 C20 0.0381(6) 0.0185(5) 0.0214(5) 0.0000(4) 0.0022(5) -0.0033(4) C21 0.0394(6) 0.0200(6) 0.0292(6) -0.0041(4) 0.0046(5) -0.0045(5) N6 0.0258(6) 0.0149(6) 0.0366(8) 0.000 0.0110(6) 0.000 C22 0.105(2) 0.0117(8) 0.0502(13) 0.000 -0.0095(13) 0.000 C23 0.0408(10) 0.0135(7) 0.0569(12) 0.000 0.0103(9) 0.000 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 C2 C1 C10 125.32(9) . . ? C2 C1 C8 107.35(9) . . ? C10 C1 C8 127.34(9) . . ? C1 C2 C3 110.44(9) . . ? C1 C2 H2 124.3(8) . . ? C3 C2 H2 125.2(8) . . ? C13 C3 C2 125.20(9) . . ? C13 C3 C9 127.23(9) . . ? C2 C3 C9 107.54(9) . . ? C9 C4 C5 118.38(11) . . ? C9 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 120.55(11) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.30(10) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 118.21(11) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C9 120.56(10) . . ? C7 C8 C1 131.79(10) . . ? C9 C8 C1 107.63(9) . . ? C4 C9 C8 121.00(10) . . ? C4 C9 C3 131.95(10) . . ? C8 C9 C3 107.02(9) . . ? C1 C10 C11 125.02(9) . . ? C1 C10 C12 119.08(9) . . ? C11 C10 C12 115.86(9) . . ? N1 C11 C10 177.47(12) . . ? N2 C12 C10 177.65(12) . . ? C3 C13 C14 125.99(9) . . ? C3 C13 C15 118.82(9) . . ? C14 C13 C15 115.18(9) . . ? N3 C14 C13 176.35(12) . . ? N4 C15 C13 178.93(12) . . ? C16 N5 C16 120.92(13) . 2_656 ? C16 N5 C22 119.54(7) . . ? C16 N5 C22 119.54(7) 2_656 . ? N5 C16 C17 120.59(10) . . ? N5 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.21(10) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C17 117.48(13) . 2_656 ? C17 C18 C19 121.26(6) . . ? C17 C18 C19 121.26(6) 2_656 . ? C20 C19 C20 117.43(14) . 2_656 ? C20 C19 C18 121.28(7) . . ? C20 C19 C18 121.28(7) 2_656 . ? C21 C20 C19 120.30(11) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? N6 C21 C20 120.82(11) . . ? N6 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 N6 C21 120.31(14) . 2_656 ? C21 N6 C23 119.85(7) . . ? C21 N6 C23 119.84(7) 2_656 . ? N5 C22 H22 109.5 . . ? N5 C22 H22A 109.5 . . ? H22 C22 H22A 109.5 . . ? N5 C22 H22B 109.5 . . ? H22 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N5 C22 H22 109.473(1) . 2_656 ? H22 C22 H22 141.1 . 2_656 ? H22A C22 H22 56.2 . 2_656 ? H22B C22 H22 56.3 . 2_656 ? N5 C22 H22A 109.473(1) . 2_656 ? H22 C22 H22A 56.3 . 2_656 ? H22A C22 H22A 141.1 . 2_656 ? H22B C22 H22A 56.3 . 2_656 ? H22 C22 H22A 109.5 2_656 2_656 ? N5 C22 H22B 109.474(2) . 2_656 ? H22 C22 H22B 56.2 . 2_656 ? H22A C22 H22B 56.3 . 2_656 ? H22B C22 H22B 141.1 . 2_656 ? H22 C22 H22B 109.5 2_656 2_656 ? H22A C22 H22B 109.5 2_656 2_656 ? N6 C23 H23 109.5 . . ? N6 C23 H23A 109.5 . . ? H23 C23 H23A 109.5 . . ? N6 C23 H23B 109.5 . . ? H23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N6 C23 H23 109.475(2) . 2_656 ? H23 C23 H23 141.1 . 2_656 ? H23A C23 H23 56.3 . 2_656 ? H23B C23 H23 56.2 . 2_656 ? N6 C23 H23A 109.475(2) . 2_656 ? H23 C23 H23A 56.2 . 2_656 ? H23A C23 H23A 141.1 . 2_656 ? H23B C23 H23A 56.3 . 2_656 ? H23 C23 H23A 109.5 2_656 2_656 ? N6 C23 H23B 109.475(1) . 2_656 ? H23 C23 H23B 56.3 . 2_656 ? H23A C23 H23B 56.3 . 2_656 ? H23B C23 H23B 141.1 . 2_656 ? H23 C23 H23B 109.5 2_656 2_656 ? H23A C23 H23B 109.5 2_656 2_656 ? 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 C2 1.3965(14) . ? C1 C10 1.4007(14) . ? C1 C8 1.4885(14) . ? C2 C3 1.4051(14) . ? C2 H2 0.966(13) . ? C3 C13 1.3905(14) . ? C3 C9 1.4872(14) . ? C4 C9 1.3802(15) . ? C4 C5 1.4099(16) . ? C4 H4 0.9500 . ? C5 C6 1.3815(18) . ? C5 H5 0.9500 . ? C6 C7 1.4069(16) . ? C6 H6 0.9500 . ? C7 C8 1.3836(14) . ? C7 H7 0.9500 . ? C8 C9 1.4149(15) . ? C10 C11 1.4220(14) . ? C10 C12 1.4250(14) . ? C11 N1 1.1522(15) . ? C12 N2 1.1541(14) . ? C13 C14 1.4250(14) . ? C13 C15 1.4264(14) . ? C14 N3 1.1537(14) . ? C15 N4 1.1518(14) . ? N5 C16 1.3460(13) . ? N5 C16 1.3461(12) 2_656 ? N5 C22 1.476(2) . ? C16 C17 1.3741(15) . ? C16 H16 0.9500 . ? C17 C18 1.3994(12) . ? C17 H17 0.9500 . ? C18 C19 1.4875(19) . ? C19 C20 1.3926(13) . ? C19 C20 1.3926(13) 2_656 ? C20 C21 1.3764(16) . ? C20 H20 0.9500 . ? C21 N6 1.3450(14) . ? C21 H21 0.9500 . ? N6 C23 1.4834(19) . ? C22 H22 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22 0.9801 2_656 ? C22 H22A 0.9800 2_656 ? C22 H22B 0.9800 2_656 ? C23 H23 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23 0.9800 2_656 ? C23 H23A 0.9800 2_656 ? C23 H23B 0.9800 2_656 ? 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 C10 C1 C2 C3 179.42(9) . . . . ? C8 C1 C2 C3 -0.42(11) . . . . ? C1 C2 C3 C13 -177.79(9) . . . . ? C1 C2 C3 C9 0.75(11) . . . . ? C9 C4 C5 C6 0.10(17) . . . . ? C4 C5 C6 C7 0.11(18) . . . . ? C5 C6 C7 C8 -0.29(17) . . . . ? C6 C7 C8 C9 0.26(15) . . . . ? C6 C7 C8 C1 -178.20(10) . . . . ? C2 C1 C8 C7 178.52(10) . . . . ? C10 C1 C8 C7 -1.32(18) . . . . ? C2 C1 C8 C9 -0.09(11) . . . . ? C10 C1 C8 C9 -179.93(10) . . . . ? C5 C4 C9 C8 -0.12(16) . . . . ? C5 C4 C9 C3 177.57(10) . . . . ? C7 C8 C9 C4 -0.06(15) . . . . ? C1 C8 C9 C4 178.74(9) . . . . ? C7 C8 C9 C3 -178.27(9) . . . . ? C1 C8 C9 C3 0.52(10) . . . . ? C13 C3 C9 C4 -0.22(18) . . . . ? C2 C3 C9 C4 -178.72(11) . . . . ? C13 C3 C9 C8 177.72(10) . . . . ? C2 C3 C9 C8 -0.78(11) . . . . ? C2 C1 C10 C11 -174.95(10) . . . . ? C8 C1 C10 C11 4.86(17) . . . . ? C2 C1 C10 C12 2.53(15) . . . . ? C8 C1 C10 C12 -177.65(9) . . . . ? C2 C3 C13 C14 -179.43(10) . . . . ? C9 C3 C13 C14 2.32(17) . . . . ? C2 C3 C13 C15 1.98(15) . . . . ? C9 C3 C13 C15 -176.27(9) . . . . ? C16 N5 C16 C17 0.45(7) 2_656 . . . ? C22 N5 C16 C17 -179.54(7) . . . . ? N5 C16 C17 C18 -0.91(15) . . . . ? C16 C17 C18 C17 0.45(7) . . . 2_656 ? C16 C17 C18 C19 -179.56(7) . . . . ? C17 C18 C19 C20 2.89(8) . . . . ? C17 C18 C19 C20 -177.11(8) 2_656 . . . ? C17 C18 C19 C20 -177.11(8) . . . 2_656 ? C17 C18 C19 C20 2.89(8) 2_656 . . 2_656 ? C20 C19 C20 C21 0.43(9) 2_656 . . . ? C18 C19 C20 C21 -179.56(9) . . . . ? C19 C20 C21 N6 -0.89(17) . . . . ? C20 C21 N6 C21 0.45(9) . . . 2_656 ? C20 C21 N6 C23 -179.55(9) . . . . ?