#------------------------------------------------------------------------------ #$Date: 2023-11-02 04:28:56 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287241 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247659.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_7247659 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 'C22 H34 N2, 2(C15 H5 N4)' _chemical_formula_sum 'C52 H44 N10' _chemical_formula_weight 808.97 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/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 110.275(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.25330(10) _cell_length_b 16.1442(3) _cell_length_c 17.4065(4) _cell_measurement_reflns_used 19557 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.5970 _cell_measurement_theta_min 1.8260 _cell_volume 2175.59(7) _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 150 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.991 _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 0.0282 _diffrn_reflns_av_unetI/netI 0.0153 _diffrn_reflns_Laue_measured_fraction_full 0.989 _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 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 29170 _diffrn_reflns_point_group_measured_fraction_full 0.989 _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 2.792 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91708 _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 Blue' _exptl_crystal_density_diffrn 1.235 _exptl_crystal_description Block _exptl_crystal_F_000 852 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.285 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 4952 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0423 _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^)+(0.0665P)^2^+0.4450P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1108 _refine_ls_wR_factor_ref 0.1142 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4486 _reflns_number_total 4952 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06782c2.cif _cod_data_source_block 20190318_HxV_-123 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247659 _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 0.984 _shelx_estimated_absorpt_t_max 0.990 _oxdiff_exptl_absorpt_empirical_full_min 0.901 _oxdiff_exptl_absorpt_empirical_full_max 1.075 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _shelx_res_file ; TITL 20190318_HP 21/n123_b R = New: P21/c 20190318_HxV_2_-123_b.res created by SHELXL-2018/3 at 10:57:59 on 22-Mar-2019 REM Yadorkari-X generated CELL 0.71073 8.2533 16.1442 17.4065 90.0000 110.2750 90.0000 ZERR 2.0 0.0001 0.0003 0.0004 0.0000 0.0020 0.0000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z REM SPGR P21/c monoclinic SFAC C H N UNIT 104 88 20 SIZE 0.21 0.17 0.14 TEMP -123.0 L.S. 50 FMAP 2 PLAN -20 ACTA CONF LIST 4 BOND $H OMIT -10.000000 55.000000 OMIT 1 0 0 OMIT -1 0 2 OMIT 0 1 1 OMIT 0 0 2 OMIT 0 2 0 OMIT 1 1 0 OMIT 0 2 1 WGHT 0.066500 0.445000 FVAR 1.24970 N1 3 0.950527 0.557820 0.401713 11.00000 0.02878 0.04985 = 0.04075 -0.00048 0.01321 0.00652 N2 3 1.032032 0.704910 0.618778 11.00000 0.02750 0.07379 = 0.04590 -0.01586 0.00886 0.00557 N3 3 0.245597 0.571590 0.184578 11.00000 0.04066 0.04473 = 0.03764 -0.00035 0.01172 0.00369 N4 3 -0.088579 0.732268 0.274335 11.00000 0.03313 0.08271 = 0.04672 0.01164 0.01297 0.02269 N5 3 0.529061 0.615292 0.676036 11.00000 0.02613 0.02481 = 0.02918 0.00047 0.01281 -0.00121 C1 1 0.524494 0.653201 0.372214 11.00000 0.02365 0.02622 = 0.03068 0.00436 0.01157 0.00257 H1 2 0.554968 0.619775 0.332807 11.00000 -1.20000 C2 1 0.642645 0.678916 0.447650 11.00000 0.02368 0.02435 = 0.03100 0.00667 0.01266 0.00066 C3 1 0.546213 0.729125 0.489317 11.00000 0.02668 0.02276 = 0.03223 0.00638 0.01393 0.00138 C4 1 0.597847 0.767964 0.564885 11.00000 0.03111 0.02745 = 0.03327 0.00391 0.01243 -0.00104 AFIX 43 H4 2 0.715293 0.766970 0.599966 11.00000 -1.20000 AFIX 0 C5 1 0.472011 0.808933 0.588407 11.00000 0.04366 0.02718 = 0.03454 0.00198 0.01963 0.00093 AFIX 43 H5 2 0.505258 0.836395 0.639818 11.00000 -1.20000 AFIX 0 C6 1 0.300473 0.809855 0.537800 11.00000 0.03990 0.03051 = 0.04131 0.00566 0.02338 0.00774 AFIX 43 H6 2 0.217533 0.837415 0.555228 11.00000 -1.20000 AFIX 0 C7 1 0.247377 0.770632 0.461086 11.00000 0.02985 0.03066 = 0.03757 0.00789 0.01568 0.00690 AFIX 43 H7 2 0.129615 0.771309 0.426410 11.00000 -1.20000 AFIX 0 C8 1 0.371077 0.730897 0.437211 11.00000 0.02697 0.02427 = 0.03068 0.00740 0.01325 0.00256 C9 1 0.357665 0.683118 0.362373 11.00000 0.02560 0.02439 = 0.03055 0.00742 0.01262 0.00300 C10 1 0.818152 0.658382 0.478943 11.00000 0.02280 0.03372 = 0.03176 0.00341 0.01100 0.00055 C11 1 0.890974 0.603651 0.435100 11.00000 0.02030 0.03877 = 0.03280 0.00598 0.00845 0.00089 C12 1 0.933688 0.685425 0.556546 11.00000 0.02273 0.04472 = 0.03966 -0.00071 0.01260 0.00197 C13 1 0.209540 0.668697 0.294926 11.00000 0.02390 0.03354 = 0.03090 0.00730 0.01053 0.00440 C14 1 0.223355 0.615980 0.231662 11.00000 0.02478 0.03574 = 0.03150 0.00724 0.00720 0.00154 C15 1 0.044446 0.703778 0.284052 11.00000 0.02877 0.04845 = 0.03229 0.00892 0.00930 0.00803 C16 1 0.673351 0.581809 0.669028 11.00000 0.02290 0.03079 = 0.02903 0.00159 0.00940 -0.00109 AFIX 43 H16 2 0.781470 0.590097 0.711432 11.00000 -1.20000 AFIX 0 C17 1 0.665721 0.535764 0.601133 11.00000 0.02120 0.02790 = 0.02886 0.00306 0.00987 0.00209 AFIX 43 H17 2 0.768030 0.512099 0.597295 11.00000 -1.20000 AFIX 0 C18 1 0.506841 0.523802 0.537621 11.00000 0.02208 0.02106 = 0.02627 0.00422 0.01058 -0.00016 C19 1 0.360737 0.559021 0.547348 11.00000 0.02087 0.03052 = 0.03077 0.00056 0.00945 0.00078 AFIX 43 H19 2 0.250853 0.551993 0.505894 11.00000 -1.20000 AFIX 0 C20 1 0.374823 0.603900 0.616658 11.00000 0.02351 0.03087 = 0.03415 -0.00016 0.01309 0.00163 AFIX 43 H20 2 0.274129 0.627165 0.622636 11.00000 -1.20000 AFIX 0 C21 1 0.540348 0.666378 0.749267 11.00000 0.03332 0.02706 = 0.03328 -0.00611 0.01562 -0.00477 AFIX 23 H21 2 0.442671 0.705935 0.734398 11.00000 -1.20000 H21A 2 0.648852 0.698815 0.766208 11.00000 -1.20000 AFIX 0 C22 1 0.536049 0.613338 0.820930 11.00000 0.03202 0.03054 = 0.02876 -0.00472 0.01248 -0.00113 AFIX 23 H22 2 0.564920 0.648676 0.870346 11.00000 -1.20000 H22A 2 0.626411 0.570173 0.831679 11.00000 -1.20000 AFIX 0 C23 1 0.362811 0.571322 0.807433 11.00000 0.03567 0.04094 = 0.03153 -0.00089 0.01311 -0.00682 AFIX 23 H23 2 0.341927 0.529113 0.763802 11.00000 -1.20000 H23A 2 0.269461 0.613073 0.788713 11.00000 -1.20000 AFIX 0 C24 1 0.356751 0.529912 0.885312 11.00000 0.03469 0.03355 = 0.03259 -0.00193 0.01439 -0.00310 AFIX 23 H24 2 0.446287 0.486187 0.902091 11.00000 -1.20000 H24A 2 0.385159 0.571628 0.929706 11.00000 -1.20000 AFIX 0 C25 1 0.182595 0.491594 0.875560 11.00000 0.04023 0.06502 = 0.04161 0.00437 0.01548 -0.01471 AFIX 23 H25 2 0.158385 0.446656 0.834411 11.00000 -1.20000 H25A 2 0.091659 0.534212 0.854576 11.00000 -1.20000 AFIX 0 C26 1 0.173816 0.456500 0.955307 11.00000 0.04207 0.05193 = 0.04484 0.00246 0.02198 -0.00791 AFIX 137 H26 2 0.263756 0.414363 0.976580 11.00000 -1.50000 H26A 2 0.060163 0.431380 0.945101 11.00000 -1.50000 H26B 2 0.191883 0.501192 0.995519 11.00000 -1.50000 AFIX 0 HKLF 4 1 1.0000 0.0000 0.0000 0.0000 -1.0000 0.0000 -1.0000 0.0000 -1.0000 REM 20190318_HP 21/n123_b R = New: P21/c REM wR2 = 0.1142, GooF = S = 1.027, Restrained GooF = 1.027 for all data REM R1 = 0.0423 for 4486 Fo > 4sig(Fo) and 0.0456 for all 4952 data REM 284 parameters refined using 0 restraints END WGHT 0.0663 0.4457 REM Highest difference peak 0.285, deepest hole -0.184, 1-sigma level 0.037 Q1 1 0.5000 0.5000 0.5000 10.50000 0.05 0.29 Q2 1 0.5987 0.7041 0.4729 11.00000 0.05 0.25 Q3 1 0.4415 0.6765 0.3614 11.00000 0.05 0.25 Q4 1 0.4559 0.7378 0.4611 11.00000 0.05 0.25 Q5 1 0.6007 0.6783 0.4007 11.00000 0.05 0.24 Q6 1 0.5321 0.6352 0.7799 11.00000 0.05 0.24 Q7 1 0.3512 0.7080 0.3985 11.00000 0.05 0.24 Q8 1 0.4336 0.5422 0.5438 11.00000 0.05 0.23 Q9 1 0.5778 0.5243 0.5708 11.00000 0.05 0.23 Q10 1 0.5278 0.7797 0.5763 11.00000 0.05 0.22 Q11 1 0.6685 0.5774 0.6233 11.00000 0.05 0.21 Q12 1 0.3652 0.5682 0.5932 11.00000 0.05 0.21 Q13 1 0.2766 0.6602 0.3366 11.00000 0.05 0.20 Q14 1 0.4437 0.5938 0.8141 11.00000 0.05 0.20 Q15 1 0.8515 0.6258 0.4576 11.00000 0.05 0.20 Q16 1 0.1718 0.4776 0.9129 11.00000 0.05 0.19 Q17 1 0.3941 0.8226 0.5557 11.00000 0.05 0.19 Q18 1 0.5313 0.6360 0.7126 11.00000 0.05 0.19 Q19 1 0.3534 0.5562 0.8461 11.00000 0.05 0.18 Q20 1 0.4475 0.6039 0.6504 11.00000 0.05 0.18 ; _shelx_res_checksum 14979 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 N1 N 0.95053(12) 0.55782(6) 0.40171(6) 0.0395(2) Uani 1 1 d . . . . . N2 N 1.03203(13) 0.70491(8) 0.61878(7) 0.0501(3) Uani 1 1 d . . . . . N3 N 0.24560(13) 0.57159(7) 0.18458(6) 0.0415(2) Uani 1 1 d . . . . . N4 N -0.08858(14) 0.73227(9) 0.27434(7) 0.0544(3) Uani 1 1 d . . . . . N5 N 0.52906(10) 0.61529(5) 0.67604(5) 0.02586(18) Uani 1 1 d . . . . . C1 C 0.52449(12) 0.65320(6) 0.37221(6) 0.0263(2) Uani 1 1 d . . . . . H1 H 0.5550(16) 0.6198(7) 0.3328(8) 0.032 Uiso 1 1 d . U . . . C2 C 0.64265(12) 0.67892(6) 0.44765(6) 0.0255(2) Uani 1 1 d . . . . . C3 C 0.54621(12) 0.72913(6) 0.48932(6) 0.0262(2) Uani 1 1 d . . . . . C4 C 0.59785(14) 0.76796(6) 0.56488(6) 0.0303(2) Uani 1 1 d . . . . . H4 H 0.715293 0.766970 0.599966 0.036 Uiso 1 1 calc R U . . . C5 C 0.47201(15) 0.80893(6) 0.58841(7) 0.0335(2) Uani 1 1 d . . . . . H5 H 0.505258 0.836395 0.639818 0.040 Uiso 1 1 calc R U . . . C6 C 0.30047(15) 0.80985(7) 0.53780(7) 0.0348(2) Uani 1 1 d . . . . . H6 H 0.217533 0.837415 0.555228 0.042 Uiso 1 1 calc R U . . . C7 C 0.24738(14) 0.77063(6) 0.46109(7) 0.0316(2) Uani 1 1 d . . . . . H7 H 0.129615 0.771309 0.426410 0.038 Uiso 1 1 calc R U . . . C8 C 0.37108(12) 0.73090(6) 0.43721(6) 0.0265(2) Uani 1 1 d . . . . . C9 C 0.35766(12) 0.68312(6) 0.36237(6) 0.0261(2) Uani 1 1 d . . . . . C10 C 0.81815(12) 0.65838(6) 0.47894(6) 0.0290(2) Uani 1 1 d . . . . . C11 C 0.89097(12) 0.60365(7) 0.43510(6) 0.0308(2) Uani 1 1 d . . . . . C12 C 0.93369(13) 0.68543(7) 0.55655(7) 0.0352(2) Uani 1 1 d . . . . . C13 C 0.20954(13) 0.66870(6) 0.29493(6) 0.0292(2) Uani 1 1 d . . . . . C14 C 0.22335(13) 0.61598(7) 0.23166(6) 0.0313(2) Uani 1 1 d . . . . . C15 C 0.04445(14) 0.70378(8) 0.28405(7) 0.0368(3) Uani 1 1 d . . . . . C16 C 0.67335(12) 0.58181(6) 0.66903(6) 0.0275(2) Uani 1 1 d . . . . . H16 H 0.781470 0.590097 0.711432 0.033 Uiso 1 1 calc R U . . . C17 C 0.66572(12) 0.53576(6) 0.60113(6) 0.0257(2) Uani 1 1 d . . . . . H17 H 0.768030 0.512099 0.597295 0.031 Uiso 1 1 calc R U . . . C18 C 0.50684(11) 0.52380(5) 0.53762(5) 0.02256(19) Uani 1 1 d . . . . . C19 C 0.36074(12) 0.55902(6) 0.54735(6) 0.0273(2) Uani 1 1 d . . . . . H19 H 0.250853 0.551993 0.505894 0.033 Uiso 1 1 calc R U . . . C20 C 0.37482(13) 0.60390(6) 0.61666(6) 0.0287(2) Uani 1 1 d . . . . . H20 H 0.274129 0.627165 0.622636 0.034 Uiso 1 1 calc R U . . . C21 C 0.54035(14) 0.66638(6) 0.74927(6) 0.0301(2) Uani 1 1 d . . . . . H21 H 0.442671 0.705935 0.734398 0.036 Uiso 1 1 calc R U . . . H21A H 0.648852 0.698815 0.766208 0.036 Uiso 1 1 calc R U . . . C22 C 0.53605(13) 0.61334(6) 0.82093(6) 0.0299(2) Uani 1 1 d . . . . . H22 H 0.564920 0.648676 0.870346 0.036 Uiso 1 1 calc R U . . . H22A H 0.626411 0.570173 0.831679 0.036 Uiso 1 1 calc R U . . . C23 C 0.36281(15) 0.57132(7) 0.80743(7) 0.0357(2) Uani 1 1 d . . . . . H23 H 0.341927 0.529113 0.763802 0.043 Uiso 1 1 calc R U . . . H23A H 0.269461 0.613073 0.788713 0.043 Uiso 1 1 calc R U . . . C24 C 0.35675(14) 0.52991(7) 0.88531(6) 0.0329(2) Uani 1 1 d . . . . . H24 H 0.446287 0.486187 0.902091 0.039 Uiso 1 1 calc R U . . . H24A H 0.385159 0.571628 0.929706 0.039 Uiso 1 1 calc R U . . . C25 C 0.18259(17) 0.49159(9) 0.87556(8) 0.0486(3) Uani 1 1 d . . . . . H25 H 0.158385 0.446656 0.834411 0.058 Uiso 1 1 calc R U . . . H25A H 0.091659 0.534212 0.854576 0.058 Uiso 1 1 calc R U . . . C26 C 0.17382(17) 0.45650(9) 0.95531(8) 0.0445(3) Uani 1 1 d . . . . . H26 H 0.263756 0.414363 0.976580 0.067 Uiso 1 1 calc R U . . . H26A H 0.060163 0.431380 0.945101 0.067 Uiso 1 1 calc R U . . . H26B H 0.191883 0.501192 0.995519 0.067 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 0.0288(5) 0.0498(6) 0.0407(5) -0.0005(4) 0.0132(4) 0.0065(4) N2 0.0275(5) 0.0738(8) 0.0459(6) -0.0159(5) 0.0089(4) 0.0056(5) N3 0.0407(5) 0.0447(6) 0.0376(5) -0.0003(4) 0.0117(4) 0.0037(4) N4 0.0331(5) 0.0827(9) 0.0467(6) 0.0116(6) 0.0130(5) 0.0227(5) N5 0.0261(4) 0.0248(4) 0.0292(4) 0.0005(3) 0.0128(3) -0.0012(3) C1 0.0237(4) 0.0262(4) 0.0307(5) 0.0044(4) 0.0116(4) 0.0026(3) C2 0.0237(4) 0.0244(4) 0.0310(5) 0.0067(4) 0.0127(4) 0.0007(3) C3 0.0267(5) 0.0228(4) 0.0322(5) 0.0064(4) 0.0139(4) 0.0014(3) C4 0.0311(5) 0.0274(5) 0.0333(5) 0.0039(4) 0.0124(4) -0.0010(4) C5 0.0437(6) 0.0272(5) 0.0345(5) 0.0020(4) 0.0196(5) 0.0009(4) C6 0.0399(6) 0.0305(5) 0.0413(6) 0.0057(4) 0.0234(5) 0.0077(4) C7 0.0299(5) 0.0307(5) 0.0376(5) 0.0079(4) 0.0157(4) 0.0069(4) C8 0.0270(5) 0.0243(4) 0.0307(5) 0.0074(4) 0.0132(4) 0.0026(3) C9 0.0256(5) 0.0244(4) 0.0305(5) 0.0074(4) 0.0126(4) 0.0030(3) C10 0.0228(5) 0.0337(5) 0.0318(5) 0.0034(4) 0.0110(4) 0.0006(4) C11 0.0203(4) 0.0388(5) 0.0328(5) 0.0060(4) 0.0085(4) 0.0009(4) C12 0.0227(5) 0.0447(6) 0.0397(6) -0.0007(5) 0.0126(4) 0.0020(4) C13 0.0239(5) 0.0335(5) 0.0309(5) 0.0073(4) 0.0105(4) 0.0044(4) C14 0.0248(5) 0.0357(5) 0.0315(5) 0.0072(4) 0.0072(4) 0.0015(4) C15 0.0288(5) 0.0485(6) 0.0323(5) 0.0089(5) 0.0093(4) 0.0080(5) C16 0.0229(4) 0.0308(5) 0.0290(5) 0.0016(4) 0.0094(4) -0.0011(4) C17 0.0212(4) 0.0279(4) 0.0289(5) 0.0031(4) 0.0099(4) 0.0021(3) C18 0.0221(4) 0.0211(4) 0.0263(4) 0.0042(3) 0.0106(3) -0.0002(3) C19 0.0209(4) 0.0305(5) 0.0308(5) 0.0006(4) 0.0094(4) 0.0008(4) C20 0.0235(4) 0.0309(5) 0.0341(5) -0.0002(4) 0.0131(4) 0.0016(4) C21 0.0333(5) 0.0271(5) 0.0333(5) -0.0061(4) 0.0156(4) -0.0048(4) C22 0.0320(5) 0.0305(5) 0.0288(5) -0.0047(4) 0.0125(4) -0.0011(4) C23 0.0357(6) 0.0409(6) 0.0315(5) -0.0009(4) 0.0131(4) -0.0068(4) C24 0.0347(5) 0.0335(5) 0.0326(5) -0.0019(4) 0.0144(4) -0.0031(4) C25 0.0402(7) 0.0650(8) 0.0416(6) 0.0044(6) 0.0155(5) -0.0147(6) C26 0.0421(6) 0.0519(7) 0.0448(6) 0.0025(5) 0.0220(5) -0.0079(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C20 N5 C16 120.31(8) . . ? C20 N5 C21 119.58(8) . . ? C16 N5 C21 120.11(8) . . ? C2 C1 C9 110.20(9) . . ? C2 C1 H1 124.1(7) . . ? C9 C1 H1 125.7(7) . . ? C10 C2 C1 125.84(9) . . ? C10 C2 C3 126.54(9) . . ? C1 C2 C3 107.59(8) . . ? C4 C3 C8 120.62(9) . . ? C4 C3 C2 131.99(9) . . ? C8 C3 C2 107.36(8) . . ? C3 C4 C5 118.32(10) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 121.02(10) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.92(10) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 118.33(10) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C3 120.79(10) . . ? C7 C8 C9 131.68(9) . . ? C3 C8 C9 107.50(8) . . ? C13 C9 C1 125.47(9) . . ? C13 C9 C8 127.19(9) . . ? C1 C9 C8 107.34(8) . . ? C2 C10 C12 123.96(9) . . ? C2 C10 C11 120.58(9) . . ? C12 C10 C11 115.37(9) . . ? N1 C11 C10 177.89(11) . . ? N2 C12 C10 177.07(12) . . ? C9 C13 C15 124.45(10) . . ? C9 C13 C14 118.00(9) . . ? C15 C13 C14 117.55(9) . . ? N3 C14 C13 175.11(11) . . ? N4 C15 C13 179.16(13) . . ? N5 C16 C17 120.87(9) . . ? N5 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 120.09(9) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 117.30(9) . . ? C19 C18 C18 120.78(10) . 3_666 ? C17 C18 C18 121.92(10) . 3_666 ? C20 C19 C18 120.43(9) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? N5 C20 C19 121.00(9) . . ? N5 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? N5 C21 C22 112.09(8) . . ? N5 C21 H21 109.2 . . ? C22 C21 H21 109.2 . . ? N5 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? H21 C21 H21A 107.9 . . ? C21 C22 C23 114.23(9) . . ? C21 C22 H22 108.7 . . ? C23 C22 H22 108.7 . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? H22 C22 H22A 107.6 . . ? C22 C23 C24 112.03(9) . . ? C22 C23 H23 109.2 . . ? C24 C23 H23 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? H23 C23 H23A 107.9 . . ? C25 C24 C23 113.55(9) . . ? C25 C24 H24 108.9 . . ? C23 C24 H24 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? H24 C24 H24A 107.7 . . ? C24 C25 C26 113.04(10) . . ? C24 C25 H25 109.0 . . ? C26 C25 H25 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? H25 C25 H25A 107.8 . . ? C25 C26 H26 109.5 . . ? C25 C26 H26A 109.5 . . ? H26 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? 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 N1 C11 1.1510(14) . ? N2 C12 1.1497(15) . ? N3 C14 1.1503(15) . ? N4 C15 1.1475(15) . ? N5 C20 1.3456(13) . ? N5 C16 1.3513(12) . ? N5 C21 1.4938(12) . ? C1 C2 1.4000(14) . ? C1 C9 1.4124(13) . ? C1 H1 0.972(13) . ? C2 C10 1.3993(13) . ? C2 C3 1.4888(13) . ? C3 C4 1.3844(14) . ? C3 C8 1.4157(14) . ? C4 C5 1.4066(15) . ? C4 H4 0.9500 . ? C5 C6 1.3843(16) . ? C5 H5 0.9500 . ? C6 C7 1.4038(16) . ? C6 H6 0.9500 . ? C7 C8 1.3858(14) . ? C7 H7 0.9500 . ? C8 C9 1.4847(14) . ? C9 C13 1.3901(14) . ? C10 C12 1.4254(15) . ? C10 C11 1.4291(14) . ? C13 C15 1.4263(14) . ? C13 C14 1.4272(15) . ? C16 C17 1.3790(14) . ? C16 H16 0.9500 . ? C17 C18 1.4051(13) . ? C17 H17 0.9500 . ? C18 C19 1.3955(13) . ? C18 C18 1.4887(18) 3_666 ? C19 C20 1.3772(14) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.5235(14) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 C23 1.5254(15) . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 C24 1.5278(14) . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? C24 C25 1.5193(16) . ? C24 H24 0.9900 . ? C24 H24A 0.9900 . ? C25 C26 1.5241(17) . ? C25 H25 0.9900 . ? C25 H25A 0.9900 . ? C26 H26 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? 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 177.70(9) . . . . ? C9 C1 C2 C3 -0.26(10) . . . . ? C10 C2 C3 C4 0.74(16) . . . . ? C1 C2 C3 C4 178.68(10) . . . . ? C10 C2 C3 C8 -177.20(9) . . . . ? C1 C2 C3 C8 0.73(10) . . . . ? C8 C3 C4 C5 0.10(14) . . . . ? C2 C3 C4 C5 -177.62(9) . . . . ? C3 C4 C5 C6 0.62(15) . . . . ? C4 C5 C6 C7 -0.68(16) . . . . ? C5 C6 C7 C8 0.00(15) . . . . ? C6 C7 C8 C3 0.72(14) . . . . ? C6 C7 C8 C9 178.60(9) . . . . ? C4 C3 C8 C7 -0.78(14) . . . . ? C2 C3 C8 C7 177.45(8) . . . . ? C4 C3 C8 C9 -179.12(8) . . . . ? C2 C3 C8 C9 -0.90(10) . . . . ? C2 C1 C9 C13 -179.48(9) . . . . ? C2 C1 C9 C8 -0.29(11) . . . . ? C7 C8 C9 C13 1.83(17) . . . . ? C3 C8 C9 C13 179.92(9) . . . . ? C7 C8 C9 C1 -177.34(10) . . . . ? C3 C8 C9 C1 0.75(10) . . . . ? C1 C2 C10 C12 -179.43(10) . . . . ? C3 C2 C10 C12 -1.86(16) . . . . ? C1 C2 C10 C11 -2.98(15) . . . . ? C3 C2 C10 C11 174.60(9) . . . . ? C1 C9 C13 C15 -175.93(10) . . . . ? C8 C9 C13 C15 5.04(16) . . . . ? C1 C9 C13 C14 3.34(15) . . . . ? C8 C9 C13 C14 -175.69(9) . . . . ? C20 N5 C16 C17 0.23(14) . . . . ? C21 N5 C16 C17 -178.79(8) . . . . ? N5 C16 C17 C18 0.67(14) . . . . ? C16 C17 C18 C19 -0.96(14) . . . . ? C16 C17 C18 C18 178.58(10) . . . 3_666 ? C17 C18 C19 C20 0.40(14) . . . . ? C18 C18 C19 C20 -179.14(10) 3_666 . . . ? C16 N5 C20 C19 -0.81(14) . . . . ? C21 N5 C20 C19 178.22(9) . . . . ? C18 C19 C20 N5 0.47(15) . . . . ? C20 N5 C21 C22 95.85(11) . . . . ? C16 N5 C21 C22 -85.11(11) . . . . ? N5 C21 C22 C23 -68.53(11) . . . . ? C21 C22 C23 C24 -171.34(9) . . . . ? C22 C23 C24 C25 176.70(10) . . . . ? C23 C24 C25 C26 -175.47(11) . . . . ?