#------------------------------------------------------------------------------ #$Date: 2023-05-05 05:21:08 +0300 (Fri, 05 May 2023) $ #$Revision: 283310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/71/26/7712657.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_7712657 loop_ _publ_author_name 'Gümrükçü, Selin' 'Özçeşmeci, Mukaddes' 'Koçyiğit, Nilüfer' 'Kaya, Kerem' 'Gül, Ahmet' 'Şahin, Yücel' 'Özçeşmeci, İbrahim' _publ_section_title ; Synthesis, fabrication and characterization of 2-naphthyloxy group-substituted bis(2-pyridylimino)isoindoline and its derivatives as a positive electrode for vanadium redox flow battery applications. ; _journal_issue 16 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 5265 _journal_page_last 5276 _journal_paper_doi 10.1039/d2dt03547b _journal_volume 52 _journal_year 2023 _chemical_formula_sum 'C30 H23 N5 O' _chemical_formula_weight 469.53 _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 geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-03-07 deposited with the CCDC. 2023-03-17 downloaded from the CCDC. ; _cell_angle_alpha 82.097(2) _cell_angle_beta 83.015(2) _cell_angle_gamma 79.848(2) _cell_formula_units_Z 2 _cell_length_a 6.3202(3) _cell_length_b 10.3082(5) _cell_length_c 19.4392(9) _cell_measurement_reflns_used 24 _cell_measurement_temperature 306(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 5 _cell_volume 1228.62(10) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 306(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type Bruker_D8_VENTURE _diffrn_measurement_method omega_and_phi_scans _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 51037 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.393 _diffrn_source Sealed_Tube _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.269 _exptl_crystal_description rod _exptl_crystal_F_000 492 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.030 _exptl_transmission_factor_max 0.987 _exptl_transmission_factor_min 0.921 _refine_diff_density_max 0.350 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 327 _refine_ls_number_reflns 4334 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0448 _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^)+(0.0638P)^2^+0.2147P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.1275 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3101 _reflns_number_total 4334 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2dt03547b2.cif _cod_data_source_block bpi_0m_a _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 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7712656--7712657.cif. ; _cod_database_code 7712657 _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_res_file ; bpi_0m_a.res created by SHELXL-2014/7 TITL bpi_0m_a.res in P-1 CELL 0.71073 6.3202 10.3082 19.4392 82.097 83.015 79.848 ZERR 2.000 0.0003 0.0005 0.0009 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 60 46 10 2 OMIT -3 50 L.S. 25 ACTA BOND $H FMAP 2 PLAN 20 TEMP 33.450 WGHT 0.063800 0.214700 FVAR 0.61996 O1 4 0.884782 0.280632 0.845197 11.00000 0.05582 0.09651 = 0.07436 -0.02548 -0.02376 0.02422 N1 3 0.288327 0.530405 0.670409 11.00000 0.04144 0.05386 = 0.05215 -0.00775 -0.00600 0.00012 N2 3 0.056963 0.601445 0.771053 11.00000 0.03887 0.05433 = 0.05610 -0.00498 -0.00287 0.00521 AFIX 43 H13 2 -0.053693 0.642416 0.750801 11.00000 -1.20000 AFIX 0 N5 3 -0.070024 0.641690 0.889034 11.00000 0.04964 0.05982 = 0.05840 -0.00653 0.00776 0.00313 N4 3 -0.332791 0.726977 0.808248 11.00000 0.04265 0.05944 = 0.07817 -0.00106 0.00066 -0.00136 N3 3 -0.069466 0.621691 0.643301 11.00000 0.04465 0.08043 = 0.06693 -0.01242 -0.01187 0.00192 C16 1 0.384797 0.480370 0.790266 11.00000 0.04088 0.04645 = 0.05090 -0.00790 -0.00436 -0.00244 C8 1 0.240954 0.539015 0.735994 11.00000 0.03863 0.04321 = 0.05479 -0.00745 -0.00222 -0.00271 C9 1 0.140881 0.586983 0.622139 11.00000 0.04419 0.04724 = 0.05734 -0.01020 -0.00889 -0.00201 C25 1 1.197171 0.115835 0.701107 11.00000 0.04879 0.04487 = 0.06417 0.00025 -0.01687 0.00016 C7 1 0.068487 0.591470 0.842040 11.00000 0.04507 0.04873 = 0.05240 -0.00433 0.00103 -0.00390 C26 1 1.130116 0.202235 0.753113 11.00000 0.04662 0.04572 = 0.07165 -0.00552 -0.01788 -0.00544 AFIX 43 H18 2 1.216174 0.263345 0.759325 11.00000 -1.20000 AFIX 0 C21 1 0.943392 0.196547 0.793466 11.00000 0.04571 0.05364 = 0.06545 -0.00456 -0.01704 0.00945 C10 1 0.220546 0.603347 0.552464 11.00000 0.05079 0.05263 = 0.05765 -0.00828 -0.00767 -0.00496 AFIX 43 H12 2 0.366851 0.576987 0.539654 11.00000 -1.20000 AFIX 0 C15 1 0.280898 0.511366 0.854119 11.00000 0.04616 0.05021 = 0.05236 -0.00876 -0.00257 -0.00156 C17 1 0.588259 0.404331 0.784003 11.00000 0.04413 0.05937 = 0.05339 -0.01259 -0.00527 0.00220 AFIX 43 H14 2 0.658014 0.385275 0.740741 11.00000 -1.20000 AFIX 0 C20 1 0.682444 0.358275 0.844750 11.00000 0.04567 0.06672 = 0.06284 -0.01283 -0.01156 0.00885 C6 1 -0.268721 0.718501 0.871792 11.00000 0.04721 0.05070 = 0.06873 0.00264 0.01008 0.00079 C24 1 1.064565 0.023345 0.692700 11.00000 0.05731 0.04059 = 0.08829 -0.00390 -0.02670 0.00078 C11 1 0.084883 0.658418 0.501827 11.00000 0.07073 0.05028 = 0.06166 -0.00277 -0.01693 -0.00965 C18 1 0.379285 0.467647 0.914351 11.00000 0.06284 0.07477 = 0.05245 -0.01220 -0.00411 0.00601 AFIX 43 H15 2 0.311275 0.489118 0.957430 11.00000 -1.20000 AFIX 0 C19 1 0.581560 0.391103 0.909049 11.00000 0.06408 0.08127 = 0.05561 -0.00909 -0.01740 0.00867 AFIX 43 H16 2 0.651372 0.361054 0.949069 11.00000 -1.20000 AFIX 0 C23 1 0.874054 0.019170 0.737087 11.00000 0.06196 0.04700 = 0.12076 0.00139 -0.02842 -0.01347 AFIX 43 H19 2 0.787115 -0.042617 0.732661 11.00000 -1.20000 AFIX 0 C22 1 0.812811 0.103107 0.786504 11.00000 0.04508 0.06679 = 0.09756 0.01071 -0.00811 -0.00509 AFIX 43 H17 2 0.685320 0.098761 0.815533 11.00000 -1.20000 AFIX 0 C13 1 -0.131913 0.693069 0.524380 11.00000 0.06907 0.07410 = 0.07544 -0.00314 -0.03157 0.00011 AFIX 43 H8 2 -0.230321 0.730002 0.492353 11.00000 -1.20000 AFIX 0 C27 1 1.389240 0.118996 0.656918 11.00000 0.06375 0.08174 = 0.07466 -0.00787 -0.00478 -0.00703 AFIX 43 H23 2 1.478569 0.178948 0.662115 11.00000 -1.20000 AFIX 0 C1 1 -0.525953 0.799200 0.797242 11.00000 0.04546 0.06534 = 0.09683 0.00737 0.00029 0.00149 AFIX 43 H1 2 -0.572442 0.805328 0.753147 11.00000 -1.20000 AFIX 0 C14 1 -0.200160 0.672840 0.593544 11.00000 0.04899 0.09590 = 0.08191 -0.01595 -0.01941 0.00655 AFIX 43 H7 2 -0.346735 0.695958 0.607158 11.00000 -1.20000 AFIX 0 C2 1 -0.658206 0.863997 0.846234 11.00000 0.05436 0.06995 = 0.11334 0.01878 0.01200 0.01113 AFIX 43 H2 2 -0.790788 0.912964 0.835503 11.00000 -1.20000 AFIX 0 C30 1 1.130571 -0.059948 0.638571 11.00000 0.09926 0.05323 = 0.11785 -0.02523 -0.04746 0.00464 AFIX 43 H20 2 1.043771 -0.120015 0.631484 11.00000 -1.20000 AFIX 0 C5 1 -0.394226 0.782879 0.924308 11.00000 0.07131 0.07763 = 0.07579 -0.00420 0.02039 0.01476 AFIX 43 H6 2 -0.344431 0.776739 0.967920 11.00000 -1.20000 AFIX 0 C12 1 0.165587 0.678546 0.426069 11.00000 0.09945 0.08983 = 0.06594 0.00885 -0.01785 -0.01372 AFIX 137 H11 2 0.314090 0.637525 0.419579 11.00000 -1.50000 H9 2 0.153650 0.771850 0.410598 11.00000 -1.50000 H10 2 0.080756 0.639165 0.399465 11.00000 -1.50000 AFIX 0 C3 1 -0.594505 0.856593 0.911721 11.00000 0.07274 0.07872 = 0.10467 0.00239 0.03063 0.02490 C29 1 1.317371 -0.052766 0.597482 11.00000 0.10856 0.09735 = 0.09643 -0.03546 -0.02905 0.02845 AFIX 43 H21 2 1.358532 -0.108379 0.562693 11.00000 -1.20000 AFIX 0 C28 1 1.447727 0.036420 0.606682 11.00000 0.08300 0.11561 = 0.07880 -0.01467 -0.00291 0.01246 AFIX 43 H22 2 1.576563 0.040013 0.578280 11.00000 -1.20000 AFIX 0 C4 1 -0.737142 0.926233 0.969080 11.00000 0.13331 0.16758 = 0.14652 -0.01340 0.05474 0.07987 AFIX 137 H4 2 -0.764678 1.019976 0.954531 11.00000 -1.50000 H5 2 -0.665189 0.909928 1.010909 11.00000 -1.50000 H3 2 -0.871481 0.892697 0.977964 11.00000 -1.50000 AFIX 0 HKLF 4 REM bpi_0m_a.res in P-1 REM R1 = 0.0448 for 3101 Fo > 4sig(Fo) and 0.0715 for all 4334 data REM 327 parameters refined using 0 restraints END WGHT 0.0647 0.2085 REM Highest difference peak 0.350, deepest hole -0.140, 1-sigma level 0.033 Q1 1 -0.9959 0.7110 1.0122 11.00000 0.05 0.35 Q2 1 0.2920 0.7235 0.4239 11.00000 0.05 0.14 Q3 1 -0.8789 0.9827 0.9413 11.00000 0.05 0.13 Q4 1 0.9804 -0.1227 0.6631 11.00000 0.05 0.13 Q5 1 0.2888 0.4595 0.8260 11.00000 0.05 0.12 Q6 1 -0.3885 0.6368 0.6249 11.00000 0.05 0.12 Q7 1 0.6772 0.4148 0.8710 11.00000 0.05 0.11 Q8 1 0.0028 0.7300 0.5178 11.00000 0.05 0.11 Q9 1 0.6873 0.4350 0.8121 11.00000 0.05 0.11 Q10 1 0.8591 0.0423 0.7829 11.00000 0.05 0.11 Q11 1 0.2488 0.4894 0.7025 11.00000 0.05 0.11 Q12 1 -0.0057 0.5624 0.6423 11.00000 0.05 0.11 Q13 1 -0.6738 1.0251 0.9454 11.00000 0.05 0.11 Q14 1 1.2399 0.1191 0.6899 11.00000 0.05 0.10 Q15 1 1.1331 0.0771 0.6929 11.00000 0.05 0.10 Q16 1 0.4026 0.5166 0.6622 11.00000 0.05 0.10 Q17 1 0.2321 0.6003 0.4071 11.00000 0.05 0.10 Q18 1 0.0400 0.6570 0.6412 11.00000 0.05 0.10 Q19 1 -0.0739 0.5989 0.7594 11.00000 0.05 0.10 Q20 1 -0.7046 0.8970 1.0230 11.00000 0.05 0.09 ; _shelx_res_checksum 6694 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 O1 O 0.8848(2) 0.28063(15) 0.84520(7) 0.0771(4) Uani 1 1 d . . . . . N1 N -0.3328(2) 0.72698(15) 0.80825(9) 0.0622(4) Uani 1 1 d . . . . . N2 N -0.0700(2) 0.64169(15) 0.88903(8) 0.0586(4) Uani 1 1 d . . . . . N3 N 0.0570(2) 0.60144(14) 0.77105(7) 0.0516(4) Uani 1 1 d . . . . . H13 H -0.0537 0.6424 0.7508 0.062 Uiso 1 1 calc R U . . . N4 N 0.2883(2) 0.53041(14) 0.67041(7) 0.0499(4) Uani 1 1 d . . . . . N5 N -0.0695(2) 0.62169(17) 0.64330(8) 0.0646(4) Uani 1 1 d . . . . . C1 C -0.5260(3) 0.7992(2) 0.79724(13) 0.0727(6) Uani 1 1 d . . . . . H1 H -0.5724 0.8053 0.7531 0.087 Uiso 1 1 calc R U . . . C2 C -0.6582(3) 0.8640(2) 0.84623(15) 0.0864(7) Uani 1 1 d . . . . . H2 H -0.7908 0.9130 0.8355 0.104 Uiso 1 1 calc R U . . . C3 C -0.5945(4) 0.8566(2) 0.91172(15) 0.0945(8) Uani 1 1 d . . . . . C4 C -0.7371(6) 0.9262(4) 0.96908(18) 0.1682(18) Uani 1 1 d . . . . . H3 H -0.8715 0.8927 0.9780 0.252 Uiso 1 1 calc R U . . . H4 H -0.7647 1.0200 0.9545 0.252 Uiso 1 1 calc R U . . . H5 H -0.6652 0.9099 1.0109 0.252 Uiso 1 1 calc R U . . . C5 C -0.3942(3) 0.7829(2) 0.92431(12) 0.0810(7) Uani 1 1 d . . . . . H6 H -0.3444 0.7767 0.9679 0.097 Uiso 1 1 calc R U . . . C6 C -0.2687(3) 0.71850(18) 0.87179(11) 0.0589(5) Uani 1 1 d . . . . . C7 C -0.2002(3) 0.6728(2) 0.59354(12) 0.0763(6) Uani 1 1 d . . . . . H7 H -0.3467 0.6960 0.6072 0.092 Uiso 1 1 calc R U . . . C8 C 0.1409(3) 0.58698(16) 0.62214(9) 0.0496(4) Uani 1 1 d . . . . . C9 C -0.1319(3) 0.6931(2) 0.52438(12) 0.0728(6) Uani 1 1 d . . . . . H8 H -0.2303 0.7300 0.4924 0.087 Uiso 1 1 calc R U . . . C10 C 0.2205(3) 0.60335(17) 0.55246(9) 0.0538(4) Uani 1 1 d . . . . . H12 H 0.3669 0.5770 0.5397 0.065 Uiso 1 1 calc R U . . . C11 C 0.0849(3) 0.65842(18) 0.50183(10) 0.0604(5) Uani 1 1 d . . . . . C12 C 0.1656(4) 0.6785(2) 0.42607(11) 0.0862(7) Uani 1 1 d . . . . . H9 H 0.1536 0.7719 0.4106 0.129 Uiso 1 1 calc R U . . . H10 H 0.0808 0.6392 0.3995 0.129 Uiso 1 1 calc R U . . . H11 H 0.3141 0.6375 0.4196 0.129 Uiso 1 1 calc R U . . . C13 C 0.0685(3) 0.59147(16) 0.84204(9) 0.0498(4) Uani 1 1 d . . . . . C14 C 0.2410(3) 0.53902(16) 0.73599(9) 0.0461(4) Uani 1 1 d . . . . . C15 C 0.2809(3) 0.51137(17) 0.85412(9) 0.0503(4) Uani 1 1 d . . . . . C16 C 0.3848(3) 0.48037(16) 0.79027(9) 0.0465(4) Uani 1 1 d . . . . . C17 C 0.5883(3) 0.40433(17) 0.78400(9) 0.0530(4) Uani 1 1 d . . . . . H14 H 0.6580 0.3853 0.7407 0.064 Uiso 1 1 calc R U . . . C18 C 0.3793(3) 0.4676(2) 0.91435(10) 0.0652(5) Uani 1 1 d . . . . . H15 H 0.3113 0.4891 0.9574 0.078 Uiso 1 1 calc R U . . . C19 C 0.5816(3) 0.3911(2) 0.90905(10) 0.0684(6) Uani 1 1 d . . . . . H16 H 0.6514 0.3611 0.9491 0.082 Uiso 1 1 calc R U . . . C20 C 0.6824(3) 0.35827(19) 0.84475(10) 0.0596(5) Uani 1 1 d . . . . . C21 C 0.9434(3) 0.19655(18) 0.79347(10) 0.0564(5) Uani 1 1 d . . . . . C22 C 0.8128(3) 0.1031(2) 0.78650(12) 0.0722(6) Uani 1 1 d . . . . . H17 H 0.6853 0.0988 0.8155 0.087 Uiso 1 1 calc R U . . . C23 C 0.8741(3) 0.0192(2) 0.73709(13) 0.0755(6) Uani 1 1 d . . . . . H19 H 0.7871 -0.0426 0.7327 0.091 Uiso 1 1 calc R U . . . C24 C 1.0646(3) 0.02334(17) 0.69270(11) 0.0619(5) Uani 1 1 d . . . . . C25 C 1.1972(3) 0.11583(17) 0.70111(9) 0.0533(4) Uani 1 1 d . . . . . C26 C 1.1301(3) 0.20223(17) 0.75311(10) 0.0540(5) Uani 1 1 d . . . . . H18 H 1.2162 0.2633 0.7593 0.065 Uiso 1 1 calc R U . . . C27 C 1.3892(3) 0.1190(2) 0.65692(11) 0.0743(6) Uani 1 1 d . . . . . H23 H 1.4786 0.1789 0.6621 0.089 Uiso 1 1 calc R U . . . C28 C 1.4477(4) 0.0364(3) 0.60668(13) 0.0961(8) Uani 1 1 d . . . . . H22 H 1.5766 0.0400 0.5783 0.115 Uiso 1 1 calc R U . . . C29 C 1.3174(5) -0.0528(3) 0.59748(15) 0.1025(9) Uani 1 1 d . . . . . H21 H 1.3585 -0.1084 0.5627 0.123 Uiso 1 1 calc R U . . . C30 C 1.1306(5) -0.0599(2) 0.63857(14) 0.0877(7) Uani 1 1 d . . . . . H20 H 1.0438 -0.1200 0.6315 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 O1 0.0558(8) 0.0965(11) 0.0744(9) -0.0255(8) -0.0238(7) 0.0242(7) N1 0.0427(8) 0.0594(9) 0.0782(12) -0.0011(8) 0.0007(8) -0.0014(7) N2 0.0496(9) 0.0598(9) 0.0584(9) -0.0065(7) 0.0078(7) 0.0031(7) N3 0.0389(8) 0.0543(9) 0.0561(9) -0.0050(7) -0.0029(7) 0.0052(6) N4 0.0414(8) 0.0539(9) 0.0521(9) -0.0078(7) -0.0060(7) 0.0001(6) N5 0.0446(9) 0.0804(11) 0.0669(10) -0.0124(8) -0.0119(8) 0.0019(8) C1 0.0455(11) 0.0653(12) 0.0968(16) 0.0074(11) 0.0003(11) 0.0015(9) C2 0.0544(12) 0.0700(14) 0.113(2) 0.0188(13) 0.0120(14) 0.0111(11) C3 0.0727(15) 0.0787(16) 0.105(2) 0.0024(14) 0.0306(15) 0.0249(12) C4 0.133(3) 0.168(3) 0.147(3) -0.013(2) 0.055(2) 0.080(3) C5 0.0713(14) 0.0776(14) 0.0758(14) -0.0042(11) 0.0204(12) 0.0148(11) C6 0.0472(10) 0.0507(10) 0.0687(13) 0.0026(9) 0.0101(10) 0.0008(8) C7 0.0490(11) 0.0959(16) 0.0819(16) -0.0159(12) -0.0194(11) 0.0065(11) C8 0.0442(9) 0.0472(10) 0.0573(11) -0.0102(8) -0.0089(8) -0.0020(7) C9 0.0691(14) 0.0741(14) 0.0754(15) -0.0031(11) -0.0316(11) 0.0001(11) C10 0.0508(10) 0.0526(10) 0.0576(11) -0.0083(8) -0.0077(9) -0.0050(8) C11 0.0707(13) 0.0503(10) 0.0617(12) -0.0028(9) -0.0169(10) -0.0096(9) C12 0.0995(17) 0.0898(16) 0.0659(14) 0.0089(12) -0.0178(13) -0.0137(13) C13 0.0451(9) 0.0487(10) 0.0524(11) -0.0043(8) 0.0010(8) -0.0039(8) C14 0.0386(9) 0.0432(9) 0.0548(11) -0.0075(8) -0.0022(8) -0.0027(7) C15 0.0462(9) 0.0502(10) 0.0524(10) -0.0088(8) -0.0026(8) -0.0016(8) C16 0.0409(9) 0.0465(9) 0.0509(10) -0.0079(7) -0.0044(8) -0.0024(7) C17 0.0441(9) 0.0594(11) 0.0534(11) -0.0126(8) -0.0053(8) 0.0022(8) C18 0.0628(12) 0.0748(13) 0.0525(11) -0.0122(9) -0.0041(9) 0.0060(10) C19 0.0641(12) 0.0813(14) 0.0556(12) -0.0091(10) -0.0174(10) 0.0087(10) C20 0.0457(10) 0.0667(12) 0.0628(12) -0.0128(9) -0.0116(9) 0.0089(9) C21 0.0457(10) 0.0536(11) 0.0655(12) -0.0046(9) -0.0170(9) 0.0094(8) C22 0.0451(11) 0.0668(13) 0.0976(16) 0.0107(12) -0.0081(10) -0.0051(10) C23 0.0620(13) 0.0470(11) 0.1208(19) 0.0014(12) -0.0284(13) -0.0135(9) C24 0.0573(12) 0.0406(10) 0.0883(14) -0.0039(9) -0.0267(11) 0.0008(8) C25 0.0488(10) 0.0449(10) 0.0642(11) 0.0002(8) -0.0169(9) 0.0002(8) C26 0.0466(10) 0.0457(10) 0.0717(12) -0.0055(9) -0.0179(9) -0.0054(8) C27 0.0638(13) 0.0817(15) 0.0747(14) -0.0079(12) -0.0048(11) -0.0070(11) C28 0.0830(17) 0.116(2) 0.0788(17) -0.0147(15) -0.0029(14) 0.0125(16) C29 0.109(2) 0.097(2) 0.096(2) -0.0355(16) -0.0291(18) 0.0285(18) C30 0.0993(19) 0.0532(12) 0.118(2) -0.0252(13) -0.0475(17) 0.0046(12) 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' O O 0.0106 0.0060 '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 O1 C21 116.68(14) . . ? C6 N1 C1 117.25(18) . . ? C13 N2 C6 121.19(16) . . ? C13 N3 H13 123.5 . . ? C14 N3 H13 123.5 . . ? C14 N3 C13 113.01(14) . . ? C14 N4 C8 121.14(14) . . ? C7 N5 C8 116.76(17) . . ? N1 C1 H1 117.9 . . ? N1 C1 C2 124.2(2) . . ? C2 C1 H1 117.9 . . ? C1 C2 H2 120.4 . . ? C1 C2 C3 119.3(2) . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 C5 117.6(2) . . ? C5 C3 C4 120.8(3) . . ? C3 C4 H3 109.5 . . ? C3 C4 H4 109.5 . . ? C3 C4 H5 109.5 . . ? H4 C4 H3 109.5 . . ? H4 C4 H5 109.5 . . ? H5 C4 H3 109.5 . . ? C3 C5 H6 120.1 . . ? C6 C5 C3 119.8(2) . . ? C6 C5 H6 120.1 . . ? N1 C6 N2 121.45(16) . . ? N1 C6 C5 121.83(18) . . ? C5 C6 N2 116.71(19) . . ? N5 C7 H7 117.9 . . ? N5 C7 C9 124.13(19) . . ? C9 C7 H7 117.9 . . ? N5 C8 N4 120.63(16) . . ? N5 C8 C10 122.04(16) . . ? C10 C8 N4 117.32(15) . . ? C7 C9 H8 120.1 . . ? C7 C9 C11 119.74(18) . . ? C11 C9 H8 120.1 . . ? C8 C10 H12 119.7 . . ? C11 C10 C8 120.64(17) . . ? C11 C10 H12 119.7 . . ? C9 C11 C12 121.21(19) . . ? C10 C11 C9 116.67(18) . . ? C10 C11 C12 122.12(19) . . ? C11 C12 H9 109.5 . . ? C11 C12 H10 109.5 . . ? C11 C12 H11 109.5 . . ? H9 C12 H10 109.5 . . ? H11 C12 H9 109.5 . . ? H11 C12 H10 109.5 . . ? N2 C13 N3 128.97(16) . . ? N2 C13 C15 125.64(16) . . ? N3 C13 C15 105.38(14) . . ? N3 C14 C16 105.37(14) . . ? N4 C14 N3 130.03(15) . . ? N4 C14 C16 124.60(14) . . ? C16 C15 C13 108.00(15) . . ? C18 C15 C13 131.59(16) . . ? C18 C15 C16 120.42(16) . . ? C15 C16 C14 108.22(14) . . ? C15 C16 C17 122.15(16) . . ? C17 C16 C14 129.62(15) . . ? C16 C17 H14 121.6 . . ? C20 C17 C16 116.88(16) . . ? C20 C17 H14 121.6 . . ? C15 C18 H15 120.9 . . ? C15 C18 C19 118.15(17) . . ? C19 C18 H15 120.9 . . ? C18 C19 H16 119.5 . . ? C18 C19 C20 120.91(17) . . ? C20 C19 H16 119.5 . . ? O1 C20 C19 116.32(16) . . ? C17 C20 O1 122.19(16) . . ? C17 C20 C19 121.45(16) . . ? O1 C21 C22 119.87(18) . . ? C26 C21 O1 119.00(17) . . ? C26 C21 C22 121.06(18) . . ? C21 C22 H17 120.3 . . ? C23 C22 C21 119.48(19) . . ? C23 C22 H17 120.3 . . ? C22 C23 H19 119.2 . . ? C22 C23 C24 121.58(19) . . ? C24 C23 H19 119.2 . . ? C23 C24 C25 118.50(19) . . ? C23 C24 C30 123.2(2) . . ? C25 C24 C30 118.3(2) . . ? C24 C25 C26 118.89(17) . . ? C27 C25 C24 118.39(18) . . ? C27 C25 C26 122.72(18) . . ? C21 C26 C25 120.46(17) . . ? C21 C26 H18 119.8 . . ? C25 C26 H18 119.8 . . ? C25 C27 H23 119.3 . . ? C28 C27 C25 121.4(2) . . ? C28 C27 H23 119.3 . . ? C27 C28 H22 119.8 . . ? C27 C28 C29 120.5(3) . . ? C29 C28 H22 119.8 . . ? C28 C29 H21 119.7 . . ? C30 C29 C28 120.5(2) . . ? C30 C29 H21 119.7 . . ? C24 C30 H20 119.6 . . ? C29 C30 C24 120.9(2) . . ? C29 C30 H20 119.6 . . ? 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 O1 C20 1.384(2) . ? O1 C21 1.391(2) . ? N1 C1 1.338(2) . ? N1 C6 1.333(2) . ? N2 C6 1.413(2) . ? N2 C13 1.282(2) . ? N3 H13 0.8600 . ? N3 C13 1.379(2) . ? N3 C14 1.377(2) . ? N4 C8 1.400(2) . ? N4 C14 1.285(2) . ? N5 C7 1.340(2) . ? N5 C8 1.343(2) . ? C1 H1 0.9300 . ? C1 C2 1.355(3) . ? C2 H2 0.9300 . ? C2 C3 1.370(4) . ? C3 C4 1.523(3) . ? C4 H3 0.9600 . ? C4 H4 0.9600 . ? C4 H5 0.9600 . ? C5 C3 1.387(3) . ? C5 H6 0.9300 . ? C6 C5 1.384(3) . ? C7 H7 0.9300 . ? C8 C10 1.385(2) . ? C9 C7 1.360(3) . ? C9 H8 0.9300 . ? C10 H12 0.9300 . ? C10 C11 1.381(2) . ? C11 C9 1.386(3) . ? C11 C12 1.498(3) . ? C12 H9 0.9600 . ? C12 H10 0.9600 . ? C12 H11 0.9600 . ? C13 C15 1.474(2) . ? C15 C18 1.376(2) . ? C16 C14 1.473(2) . ? C16 C15 1.382(2) . ? C16 C17 1.384(2) . ? C17 H14 0.9300 . ? C17 C20 1.375(2) . ? C18 H15 0.9300 . ? C18 C19 1.379(3) . ? C19 H16 0.9300 . ? C20 C19 1.389(3) . ? C21 C22 1.404(3) . ? C22 H17 0.9300 . ? C23 C22 1.357(3) . ? C23 H19 0.9300 . ? C24 C23 1.397(3) . ? C24 C30 1.426(3) . ? C25 C24 1.413(3) . ? C25 C26 1.416(2) . ? C25 C27 1.402(3) . ? C26 C21 1.341(3) . ? C26 H18 0.9300 . ? C27 H23 0.9300 . ? C27 C28 1.358(3) . ? C28 H22 0.9300 . ? C29 C28 1.380(4) . ? C29 H21 0.9300 . ? C30 C29 1.350(4) . ? C30 H20 0.9300 . ?