#------------------------------------------------------------------------------ #$Date: 2023-11-02 04:28:56 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287241 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247658.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_7247658 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 'C18 H26 N2, 2(C15 H5 N4)' _chemical_formula_sum 'C48 H36 N10' _chemical_formula_weight 752.87 _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 107.219(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.8550(2) _cell_length_b 18.6894(3) _cell_length_c 10.1304(2) _cell_measurement_reflns_used 19567 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.5470 _cell_measurement_theta_min 2.1230 _cell_volume 1963.08(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 0.984 _diffrn_measured_fraction_theta_max 0.988 _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 0.0234 _diffrn_reflns_av_unetI/netI 0.0122 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 25997 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.496 _diffrn_reflns_theta_min 3.030 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90179 _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 'Dark blue' _exptl_crystal_density_diffrn 1.274 _exptl_crystal_description Platelet _exptl_crystal_F_000 788 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.473 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.088 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 4450 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0460 _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^)+(0.0852P)^2^+0.3892P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1280 _refine_ls_wR_factor_ref 0.1343 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4137 _reflns_number_total 4450 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06782c2.cif _cod_data_source_block 20190316_BV_-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_cell_volume 1963.08(6) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247658 _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 0.997 _oxdiff_exptl_absorpt_empirical_full_min 0.865 _oxdiff_exptl_absorpt_empirical_full_max 1.144 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _shelx_res_file ; TITL 20190316_BP c123 R = New: P21/c 20190316_BV_-123.res created by SHELXL-2018/3 at 15:24:45 on 20-Mar-2019 REM Yadorkari-X generated CELL 0.71073 10.8550 18.6894 10.1304 90.0000 107.2190 90.0000 ZERR 2.0 0.0002 0.0003 0.0002 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 96 72 20 SIZE 0.20 0.10 0.04 TEMP -123.0 L.S. 50 FMAP 2 PLAN -20 ACTA CONF LIST 4 BOND $H OMIT -10.000000 55.000000 OMIT 0 1 1 OMIT 0 2 0 OMIT 1 0 0 OMIT 1 1 0 OMIT -1 1 1 OMIT 1 2 0 WGHT 0.085200 0.389200 FVAR 13.78656 N1 3 -0.558158 0.745084 0.396076 11.00000 0.04055 0.02420 = 0.06011 0.00449 0.02330 0.00300 N2 3 -0.148947 0.679980 0.490823 11.00000 0.03318 0.03408 = 0.05572 -0.00173 0.00993 -0.00710 N3 3 -0.900287 0.495912 0.216944 11.00000 0.02472 0.03716 = 0.05038 -0.00136 0.00474 0.00284 N4 3 -0.679498 0.298406 0.254692 11.00000 0.03585 0.02407 = 0.04067 -0.00234 0.01142 -0.00235 N5 3 0.216581 0.102049 0.381449 11.00000 0.02063 0.02354 = 0.02642 0.00090 0.00647 0.00403 C1 1 -0.560833 0.552700 0.329148 11.00000 0.02139 0.02029 = 0.02402 0.00180 0.00704 0.00248 H1 2 -0.635667 0.583670 0.319300 11.00000 -1.20000 C2 1 -0.431450 0.576139 0.374145 11.00000 0.02352 0.02082 = 0.01926 0.00170 0.00695 0.00130 C3 1 -0.348367 0.512249 0.380046 11.00000 0.02282 0.02199 = 0.02113 0.00057 0.00609 0.00228 C4 1 -0.215690 0.504042 0.415728 11.00000 0.02131 0.03073 = 0.03207 -0.00134 0.00355 0.00124 AFIX 43 H4 2 -0.159840 0.543692 0.446698 11.00000 -1.20000 AFIX 0 C5 1 -0.165863 0.435775 0.405008 11.00000 0.02301 0.03683 = 0.04553 0.00040 0.00542 0.00813 AFIX 43 H5 2 -0.075145 0.429219 0.428629 11.00000 -1.20000 AFIX 0 C6 1 -0.246663 0.377988 0.360657 11.00000 0.03153 0.02760 = 0.04904 0.00073 0.01138 0.01129 AFIX 43 H6 2 -0.210772 0.332435 0.352495 11.00000 -1.20000 AFIX 0 C7 1 -0.381099 0.385467 0.327406 11.00000 0.02910 0.02127 = 0.03498 0.00017 0.00979 0.00397 AFIX 43 H7 2 -0.436449 0.345442 0.298351 11.00000 -1.20000 AFIX 0 C8 1 -0.430912 0.452717 0.338068 11.00000 0.02214 0.02162 = 0.02135 0.00151 0.00684 0.00232 C9 1 -0.565870 0.478647 0.308789 11.00000 0.02176 0.02138 = 0.01887 0.00162 0.00661 0.00187 C10 1 -0.389986 0.646089 0.406041 11.00000 0.02600 0.02101 = 0.02542 0.00031 0.00838 -0.00050 C11 1 -0.482247 0.701652 0.399519 11.00000 0.03149 0.02050 = 0.03363 0.00057 0.01241 -0.00357 C12 1 -0.256859 0.665592 0.452746 11.00000 0.03103 0.02305 = 0.03262 -0.00135 0.00976 -0.00310 C13 1 -0.677460 0.436118 0.269072 11.00000 0.02190 0.02115 = 0.02364 0.00167 0.00677 0.00091 C14 1 -0.800828 0.468716 0.241181 11.00000 0.02472 0.02396 = 0.02766 -0.00030 0.00532 -0.00274 C15 1 -0.676770 0.360025 0.260412 11.00000 0.02391 0.02580 = 0.02533 -0.00021 0.00745 -0.00084 C16 1 0.208757 0.030594 0.398782 11.00000 0.01978 0.02455 = 0.03499 -0.00177 0.00589 -0.00032 AFIX 43 H16 2 0.126579 0.008328 0.378416 11.00000 -1.20000 AFIX 0 C17 1 0.318564 -0.010098 0.445576 11.00000 0.02109 0.02019 = 0.03447 -0.00164 0.00675 -0.00040 AFIX 43 H17 2 0.311749 -0.060220 0.457384 11.00000 -1.20000 AFIX 0 C18 1 0.440167 0.021830 0.475883 11.00000 0.01863 0.02113 = 0.01986 -0.00219 0.00606 0.00118 C19 1 0.444507 0.095880 0.459264 11.00000 0.02039 0.02249 = 0.03092 -0.00030 0.00809 -0.00108 AFIX 43 H19 2 0.525436 0.119620 0.481044 11.00000 -1.20000 AFIX 0 C20 1 0.331959 0.134816 0.411390 11.00000 0.02506 0.02004 = 0.03199 0.00126 0.00957 0.00077 AFIX 43 H20 2 0.336007 0.185093 0.399506 11.00000 -1.20000 AFIX 0 C21 1 0.094704 0.144122 0.333086 11.00000 0.02228 0.02916 = 0.03376 0.00476 0.00531 0.00859 AFIX 23 H21 2 0.034344 0.119894 0.252817 11.00000 -1.20000 H21A 2 0.113600 0.192269 0.303216 11.00000 -1.20000 AFIX 0 C22 1 0.032599 0.151192 0.448573 11.00000 0.02587 0.02405 = 0.04122 -0.00102 0.01205 0.00316 AFIX 23 H22 2 0.089646 0.179590 0.524947 11.00000 -1.20000 H22A 2 0.022495 0.103085 0.484949 11.00000 -1.20000 AFIX 0 C23 1 -0.098512 0.187228 0.398407 11.00000 0.02893 0.03531 = 0.07359 0.00174 0.02052 0.00957 AFIX 23 H23 2 -0.157998 0.156778 0.327694 11.00000 -1.20000 H23A 2 -0.089719 0.233627 0.354919 11.00000 -1.20000 AFIX 0 C24 1 -0.154899 0.199721 0.517992 11.00000 0.06684 0.04831 = 0.12196 0.01539 0.06893 0.01508 AFIX 137 H24 2 -0.153857 0.154752 0.568068 11.00000 -1.50000 H24A 2 -0.243895 0.216821 0.481621 11.00000 -1.50000 H24B 2 -0.103104 0.235600 0.580967 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM 20190316_BP c123 R = New: P21/c REM wR2 = 0.1343, GooF = S = 1.088, Restrained GooF = 1.088 for all data REM R1 = 0.0460 for 4137 Fo > 4sig(Fo) and 0.0498 for all 4450 data REM 266 parameters refined using 0 restraints END WGHT 0.0852 0.3891 REM Highest difference peak 0.473, deepest hole -0.367, 1-sigma level 0.088 Q1 1 -0.5000 0.5000 0.0000 10.50000 0.05 0.47 Q2 1 -0.7385 0.4539 0.2633 11.00000 0.05 0.36 Q3 1 -0.6172 0.4940 -0.0215 11.00000 0.05 0.31 Q4 1 -0.6276 0.4571 0.2836 11.00000 0.05 0.31 Q5 1 -0.4479 0.5573 0.0219 11.00000 0.05 0.30 Q6 1 -0.8370 0.4750 0.2847 11.00000 0.05 0.29 Q7 1 -0.8085 0.6817 0.0682 11.00000 0.05 0.28 Q8 1 -0.5747 0.5199 0.3026 11.00000 0.05 0.27 Q9 1 -0.3917 0.6110 0.0811 11.00000 0.05 0.26 Q10 1 -0.6776 0.3990 0.2699 11.00000 0.05 0.25 Q11 1 -0.4984 0.5689 0.3447 11.00000 0.05 0.24 Q12 1 -0.3228 0.6519 0.4307 11.00000 0.05 0.23 Q13 1 -0.1175 0.5554 0.5834 11.00000 0.05 0.23 Q14 1 -0.0985 0.6005 0.5799 11.00000 0.05 0.22 Q15 1 -0.6204 0.5982 0.1032 11.00000 0.05 0.22 Q16 1 -0.6945 0.6152 0.1603 11.00000 0.05 0.22 Q17 1 -0.4132 0.6104 0.3686 11.00000 0.05 0.22 Q18 1 -0.1769 0.5871 0.5850 11.00000 0.05 0.21 Q19 1 -0.6484 0.5475 0.1822 11.00000 0.05 0.21 Q20 1 -0.5969 0.5735 0.0965 11.00000 0.05 0.21 ; _shelx_res_checksum 42153 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 -0.55816(11) 0.74508(6) 0.39608(13) 0.0398(3) Uani 1 1 d . . . . . N2 N -0.14895(11) 0.67998(6) 0.49082(13) 0.0417(3) Uani 1 1 d . . . . . N3 N -0.90029(10) 0.49591(6) 0.21694(12) 0.0388(3) Uani 1 1 d . . . . . N4 N -0.67950(10) 0.29841(5) 0.25469(11) 0.0335(2) Uani 1 1 d . . . . . N5 N 0.21658(8) 0.10205(5) 0.38145(9) 0.0236(2) Uani 1 1 d . . . . . C1 C -0.56083(9) 0.55270(5) 0.32915(10) 0.0218(2) Uani 1 1 d . . . . . H1 H -0.6357(13) 0.5837(7) 0.3193(13) 0.026 Uiso 1 1 d . U . . . C2 C -0.43145(10) 0.57614(5) 0.37415(10) 0.0211(2) Uani 1 1 d . . . . . C3 C -0.34837(10) 0.51225(5) 0.38005(10) 0.0221(2) Uani 1 1 d . . . . . C4 C -0.21569(10) 0.50404(6) 0.41573(12) 0.0290(2) Uani 1 1 d . . . . . H4 H -0.159840 0.543692 0.446698 0.035 Uiso 1 1 calc R U . . . C5 C -0.16586(11) 0.43578(7) 0.40501(14) 0.0361(3) Uani 1 1 d . . . . . H5 H -0.075145 0.429219 0.428629 0.043 Uiso 1 1 calc R U . . . C6 C -0.24666(12) 0.37799(7) 0.36066(14) 0.0362(3) Uani 1 1 d . . . . . H6 H -0.210772 0.332435 0.352495 0.043 Uiso 1 1 calc R U . . . C7 C -0.38110(11) 0.38547(6) 0.32741(12) 0.0284(2) Uani 1 1 d . . . . . H7 H -0.436449 0.345442 0.298351 0.034 Uiso 1 1 calc R U . . . C8 C -0.43091(9) 0.45272(5) 0.33807(10) 0.0216(2) Uani 1 1 d . . . . . C9 C -0.56587(9) 0.47865(5) 0.30879(9) 0.0205(2) Uani 1 1 d . . . . . C10 C -0.38999(10) 0.64609(5) 0.40604(10) 0.0240(2) Uani 1 1 d . . . . . C11 C -0.48225(11) 0.70165(6) 0.39952(11) 0.0279(2) Uani 1 1 d . . . . . C12 C -0.25686(11) 0.66559(6) 0.45275(12) 0.0288(2) Uani 1 1 d . . . . . C13 C -0.67746(10) 0.43612(5) 0.26907(10) 0.0222(2) Uani 1 1 d . . . . . C14 C -0.80083(10) 0.46872(6) 0.24118(11) 0.0260(2) Uani 1 1 d . . . . . C15 C -0.67677(10) 0.36003(6) 0.26041(10) 0.0250(2) Uani 1 1 d . . . . . C16 C 0.20876(10) 0.03059(6) 0.39878(11) 0.0269(2) Uani 1 1 d . . . . . H16 H 0.126579 0.008328 0.378416 0.032 Uiso 1 1 calc R U . . . C17 C 0.31856(10) -0.01010(6) 0.44558(11) 0.0256(2) Uani 1 1 d . . . . . H17 H 0.311749 -0.060220 0.457384 0.031 Uiso 1 1 calc R U . . . C18 C 0.44017(9) 0.02183(5) 0.47588(9) 0.0198(2) Uani 1 1 d . . . . . C19 C 0.44451(10) 0.09588(6) 0.45926(11) 0.0245(2) Uani 1 1 d . . . . . H19 H 0.525436 0.119620 0.481044 0.029 Uiso 1 1 calc R U . . . C20 C 0.33196(10) 0.13482(6) 0.41139(11) 0.0255(2) Uani 1 1 d . . . . . H20 H 0.336007 0.185093 0.399506 0.031 Uiso 1 1 calc R U . . . C21 C 0.09470(10) 0.14412(6) 0.33309(12) 0.0290(2) Uani 1 1 d . . . . . H21 H 0.034344 0.119894 0.252817 0.035 Uiso 1 1 calc R U . . . H21A H 0.113600 0.192269 0.303216 0.035 Uiso 1 1 calc R U . . . C22 C 0.03260(11) 0.15119(6) 0.44857(13) 0.0299(2) Uani 1 1 d . . . . . H22 H 0.089646 0.179590 0.524947 0.036 Uiso 1 1 calc R U . . . H22A H 0.022495 0.103085 0.484949 0.036 Uiso 1 1 calc R U . . . C23 C -0.09851(12) 0.18723(8) 0.39841(17) 0.0448(3) Uani 1 1 d . . . . . H23 H -0.157998 0.156778 0.327694 0.054 Uiso 1 1 calc R U . . . H23A H -0.089719 0.233627 0.354919 0.054 Uiso 1 1 calc R U . . . C24 C -0.15490(19) 0.19972(10) 0.5180(2) 0.0702(6) Uani 1 1 d . . . . . H24 H -0.153857 0.154752 0.568068 0.105 Uiso 1 1 calc R U . . . H24A H -0.243895 0.216821 0.481621 0.105 Uiso 1 1 calc R U . . . H24B H -0.103104 0.235600 0.580967 0.105 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 0.0405(6) 0.0242(5) 0.0601(7) 0.0045(4) 0.0233(5) 0.0030(4) N2 0.0332(6) 0.0341(6) 0.0557(7) -0.0017(5) 0.0099(5) -0.0071(4) N3 0.0247(5) 0.0372(6) 0.0504(6) -0.0014(5) 0.0047(4) 0.0028(4) N4 0.0358(5) 0.0241(5) 0.0407(5) -0.0023(4) 0.0114(4) -0.0024(4) N5 0.0206(4) 0.0235(4) 0.0264(4) 0.0009(3) 0.0065(3) 0.0040(3) C1 0.0214(5) 0.0203(5) 0.0240(5) 0.0018(4) 0.0070(4) 0.0025(4) C2 0.0235(5) 0.0208(5) 0.0193(4) 0.0017(3) 0.0070(4) 0.0013(4) C3 0.0228(5) 0.0220(5) 0.0211(4) 0.0006(3) 0.0061(4) 0.0023(4) C4 0.0213(5) 0.0307(6) 0.0321(5) -0.0013(4) 0.0035(4) 0.0012(4) C5 0.0230(5) 0.0368(7) 0.0455(7) 0.0004(5) 0.0054(5) 0.0081(4) C6 0.0315(6) 0.0276(6) 0.0490(7) 0.0007(5) 0.0114(5) 0.0113(5) C7 0.0291(5) 0.0213(5) 0.0350(6) 0.0002(4) 0.0098(4) 0.0040(4) C8 0.0221(5) 0.0216(5) 0.0213(4) 0.0015(3) 0.0068(4) 0.0023(4) C9 0.0218(5) 0.0214(5) 0.0189(4) 0.0016(3) 0.0066(4) 0.0019(4) C10 0.0260(5) 0.0210(5) 0.0254(5) 0.0003(4) 0.0084(4) -0.0005(4) C11 0.0315(5) 0.0205(5) 0.0336(5) 0.0006(4) 0.0124(4) -0.0036(4) C12 0.0310(6) 0.0230(5) 0.0326(5) -0.0013(4) 0.0098(4) -0.0031(4) C13 0.0219(5) 0.0212(5) 0.0236(5) 0.0017(3) 0.0068(4) 0.0009(4) C14 0.0247(5) 0.0240(5) 0.0277(5) -0.0003(4) 0.0053(4) -0.0027(4) C15 0.0239(5) 0.0258(5) 0.0253(5) -0.0002(4) 0.0075(4) -0.0008(4) C16 0.0198(5) 0.0246(5) 0.0350(5) -0.0018(4) 0.0059(4) -0.0003(4) C17 0.0211(5) 0.0202(5) 0.0345(5) -0.0016(4) 0.0067(4) -0.0004(4) C18 0.0186(5) 0.0211(5) 0.0199(4) -0.0022(3) 0.0061(4) 0.0012(4) C19 0.0204(5) 0.0225(5) 0.0309(5) -0.0003(4) 0.0081(4) -0.0011(4) C20 0.0251(5) 0.0200(5) 0.0320(5) 0.0013(4) 0.0096(4) 0.0008(4) C21 0.0223(5) 0.0292(5) 0.0338(6) 0.0048(4) 0.0053(4) 0.0086(4) C22 0.0259(5) 0.0241(5) 0.0412(6) -0.0010(4) 0.0120(5) 0.0032(4) C23 0.0289(6) 0.0353(7) 0.0736(9) 0.0017(6) 0.0205(6) 0.0096(5) C24 0.0668(11) 0.0483(9) 0.1220(17) 0.0154(10) 0.0689(12) 0.0151(8) 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 120.66(9) . . ? C20 N5 C21 120.66(9) . . ? C16 N5 C21 118.64(9) . . ? C9 C1 C2 110.28(9) . . ? C9 C1 H1 125.2(8) . . ? C2 C1 H1 124.5(8) . . ? C10 C2 C1 126.15(9) . . ? C10 C2 C3 126.55(9) . . ? C1 C2 C3 107.30(8) . . ? C4 C3 C8 120.59(9) . . ? C4 C3 C2 132.11(10) . . ? C8 C3 C2 107.29(9) . . ? C3 C4 C5 118.38(10) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 120.98(11) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.03(11) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 118.27(10) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C3 120.71(9) . . ? C7 C8 C9 131.64(10) . . ? C3 C8 C9 107.63(9) . . ? C1 C9 C13 126.54(9) . . ? C1 C9 C8 107.46(9) . . ? C13 C9 C8 126.01(9) . . ? C2 C10 C12 122.93(10) . . ? C2 C10 C11 119.88(9) . . ? C12 C10 C11 117.12(9) . . ? N1 C11 C10 178.12(12) . . ? N2 C12 C10 178.72(13) . . ? C9 C13 C14 119.76(9) . . ? C9 C13 C15 124.24(9) . . ? C14 C13 C15 115.93(9) . . ? N3 C14 C13 178.81(12) . . ? N4 C15 C13 177.94(12) . . ? N5 C16 C17 120.64(9) . . ? N5 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.38(10) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 117.39(9) . . ? C19 C18 C18 121.70(11) . 3_656 ? C17 C18 C18 120.92(11) . 3_656 ? C20 C19 C18 120.44(9) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? N5 C20 C19 120.47(10) . . ? N5 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? N5 C21 C22 110.22(9) . . ? N5 C21 H21 109.6 . . ? C22 C21 H21 109.6 . . ? N5 C21 H21A 109.6 . . ? C22 C21 H21A 109.6 . . ? H21 C21 H21A 108.1 . . ? C21 C22 C23 111.48(10) . . ? C21 C22 H22 109.3 . . ? C23 C22 H22 109.3 . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? H22 C22 H22A 108.0 . . ? C22 C23 C24 110.97(14) . . ? C22 C23 H23 109.4 . . ? C24 C23 H23 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? H23 C23 H23A 108.0 . . ? C23 C24 H24 109.5 . . ? C23 C24 H24A 109.5 . . ? H24 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24 C24 H24B 109.5 . . ? H24A C24 H24B 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 1.1498(16) . ? N2 C12 1.1514(16) . ? N3 C14 1.1521(15) . ? N4 C15 1.1530(15) . ? N5 C20 1.3456(13) . ? N5 C16 1.3529(14) . ? N5 C21 1.4916(13) . ? C1 C9 1.3980(14) . ? C1 C2 1.4118(14) . ? C1 H1 0.978(14) . ? C2 C10 1.3892(14) . ? C2 C3 1.4869(13) . ? C3 C4 1.3857(14) . ? C3 C8 1.4128(14) . ? C4 C5 1.4025(17) . ? C4 H4 0.9500 . ? C5 C6 1.3799(18) . ? C5 H5 0.9500 . ? C6 C7 1.4041(16) . ? C6 H6 0.9500 . ? C7 C8 1.3850(14) . ? C7 H7 0.9500 . ? C8 C9 1.4872(13) . ? C9 C13 1.4044(14) . ? C10 C12 1.4284(15) . ? C10 C11 1.4306(15) . ? C13 C14 1.4214(14) . ? C13 C15 1.4250(14) . ? C16 C17 1.3745(14) . ? C16 H16 0.9500 . ? C17 C18 1.3974(14) . ? C17 H17 0.9500 . ? C18 C19 1.3966(14) . ? C18 C18 1.4886(18) 3_656 ? C19 C20 1.3808(14) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.5191(16) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 C23 1.5196(16) . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 C24 1.528(2) . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? C24 H24 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 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 -179.19(9) . . . . ? C9 C1 C2 C3 1.18(11) . . . . ? C10 C2 C3 C4 -0.23(18) . . . . ? C1 C2 C3 C4 179.40(11) . . . . ? C10 C2 C3 C8 -179.51(10) . . . . ? C1 C2 C3 C8 0.12(11) . . . . ? C8 C3 C4 C5 1.94(16) . . . . ? C2 C3 C4 C5 -177.27(11) . . . . ? C3 C4 C5 C6 -0.29(19) . . . . ? C4 C5 C6 C7 -1.2(2) . . . . ? C5 C6 C7 C8 1.04(18) . . . . ? C6 C7 C8 C3 0.61(16) . . . . ? C6 C7 C8 C9 178.74(11) . . . . ? C4 C3 C8 C7 -2.13(15) . . . . ? C2 C3 C8 C7 177.26(9) . . . . ? C4 C3 C8 C9 179.34(9) . . . . ? C2 C3 C8 C9 -1.28(10) . . . . ? C2 C1 C9 C13 177.57(9) . . . . ? C2 C1 C9 C8 -1.96(11) . . . . ? C7 C8 C9 C1 -176.31(11) . . . . ? C3 C8 C9 C1 2.01(11) . . . . ? C7 C8 C9 C13 4.16(17) . . . . ? C3 C8 C9 C13 -177.53(9) . . . . ? C1 C2 C10 C12 179.19(10) . . . . ? C3 C2 C10 C12 -1.24(16) . . . . ? C1 C2 C10 C11 2.47(16) . . . . ? C3 C2 C10 C11 -177.96(9) . . . . ? C1 C9 C13 C14 2.08(15) . . . . ? C8 C9 C13 C14 -178.47(9) . . . . ? C1 C9 C13 C15 -174.76(9) . . . . ? C8 C9 C13 C15 4.69(16) . . . . ? C20 N5 C16 C17 -0.88(16) . . . . ? C21 N5 C16 C17 -178.81(10) . . . . ? N5 C16 C17 C18 -0.05(16) . . . . ? C16 C17 C18 C19 1.24(15) . . . . ? C16 C17 C18 C18 -178.85(11) . . . 3_656 ? C17 C18 C19 C20 -1.55(15) . . . . ? C18 C18 C19 C20 178.54(11) 3_656 . . . ? C16 N5 C20 C19 0.56(15) . . . . ? C21 N5 C20 C19 178.45(9) . . . . ? C18 C19 C20 N5 0.68(16) . . . . ? C20 N5 C21 C22 -104.80(11) . . . . ? C16 N5 C21 C22 73.13(12) . . . . ? N5 C21 C22 C23 -174.22(10) . . . . ? C21 C22 C23 C24 -175.22(12) . . . . ?