#------------------------------------------------------------------------------ #$Date: 2024-02-04 14:16:58 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289567 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247835.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_7247835 loop_ _publ_author_name 'Yang, Zhi' 'Chen, Yu' 'Wan, Linxi' 'Li, Yuxiao' 'Chen, Dan' 'Tao, Jianlin' 'Tang, Pei' 'Chen, Fen-Er' _publ_section_title ; Iridium-catalyzed asymmetric, complete hydrogenation of pyrimidinium salts under batch and flow ; _journal_issue 1 _journal_name_full 'Green Chemistry' _journal_page_first 317 _journal_page_last 322 _journal_paper_doi 10.1039/D3GC04364A _journal_volume 26 _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C23 H24 N2' _chemical_formula_sum 'C23 H24 N2' _chemical_formula_weight 328.44 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc2f5650 _audit_creation_date 2022-11-03 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2023-02-01 deposited with the CCDC. 2023-12-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.9340(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.1560(3) _cell_length_b 6.05280(10) _cell_length_c 20.8658(4) _cell_measurement_reflns_used 9863 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 69.874 _cell_measurement_theta_min 2.192 _cell_volume 1849.50(6) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 297.0 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0342 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 33674 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.070 _diffrn_reflns_theta_max 67.070 _diffrn_reflns_theta_min 2.191 _diffrn_source_current 1.1 _diffrn_source_power 0.055 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5309 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1321 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.7048. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.180 _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.217 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 2400 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.08(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 454 _refine_ls_number_reflns 6569 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0457 _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^)+(0.0770P)^2^+0.1019P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1214 _refine_ls_wR_factor_ref 0.1257 _reflns_Friedel_coverage 0.808 _reflns_Friedel_fraction_full 0.994 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 5814 _reflns_number_total 6569 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc04364a2.cif _cod_data_source_block cu_tp_cy001_0ma_a _cod_depositor_comments 'Adding full bibliography for 7247835.cif.' _cod_database_code 7247835 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.907 _shelx_estimated_absorpt_t_min 0.798 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Riding coordinates: N3(H3a) 2.b Ternary CH refined with riding coordinates: C8(H8), C32(H32) 2.c Secondary CH2 refined with riding coordinates: C5(H5a,H5b), C6(H6a,H6b), C23(H23a,H23b), C24(H24a,H24b), C29(H29a,H29b), C30(H30a,H30b), C31(H31a,H31b), C45(H45a,H45b) 2.d Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47) ; _shelx_res_file ; cu_tp_cy001_0ma_a.res created by SHELXL-2014/7 TITL cu_TP_CY001_0ma_a.res in P2(1) CELL 1.54178 15.156 6.0528 20.8658 90 104.934 90 ZERR 4 0.0003 0.0001 0.0004 0 0.001 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N UNIT 92 96 8 L.S. 4 PLAN 20 0 0 SIZE 0.19 0.35 0.45 TEMP 23.85 CONF HTAB BOND $H fmap 2 acta MORE -1 SHEL 999 0.837 OMIT 16 -3 1 OMIT 16 3 1 OMIT 4 0 3 OMIT 5 0 0 OMIT -4 0 1 OMIT 14 0 2 OMIT 14 -1 1 OMIT -12 2 3 OMIT 11 -1 5 REM REM REM WGHT 0.077000 0.101900 FVAR 0.86312 N1 3 0.418204 0.576431 0.699122 11.00000 0.06244 0.03835 = 0.06777 -0.00447 0.02174 -0.00406 N2 3 0.898822 0.387212 0.765354 11.00000 0.06452 0.04033 = 0.05408 -0.00236 0.01161 0.00135 N3 3 0.849082 0.549668 0.655821 11.00000 0.06599 0.04091 = 0.06067 -0.00131 0.01236 0.00578 AFIX 3 H3A 2 0.899142 0.611748 0.653331 11.00000 -1.20000 AFIX 0 C1 1 0.605619 0.988139 0.569890 11.00000 0.06975 0.08419 = 0.05833 -0.00872 0.01657 -0.01961 AFIX 43 H1 2 0.648363 1.074002 0.556299 11.00000 -1.20000 AFIX 0 C2 1 0.516893 1.056878 0.557285 11.00000 0.08829 0.05442 = 0.06027 0.00029 0.01903 -0.00169 AFIX 43 H2 2 0.499365 1.190854 0.535982 11.00000 -1.20000 AFIX 0 C3 1 0.453686 0.926676 0.576303 11.00000 0.05973 0.06070 = 0.06369 -0.00183 0.01399 0.01057 AFIX 43 H3 2 0.393339 0.973842 0.567366 11.00000 -1.20000 AFIX 0 C4 1 0.477833 0.726823 0.608476 11.00000 0.06288 0.05085 = 0.05453 -0.00710 0.01715 0.00188 C5 1 0.407992 0.582452 0.627676 11.00000 0.07590 0.05706 = 0.06921 -0.01021 0.02067 -0.00830 AFIX 23 H5A 2 0.347425 0.636430 0.605897 11.00000 -1.20000 H5B 2 0.413263 0.433415 0.611980 11.00000 -1.20000 AFIX 0 C6 1 0.355251 0.414386 0.714468 11.00000 0.08413 0.04476 = 0.08419 -0.01162 0.03122 -0.01622 AFIX 23 H6A 2 0.293272 0.457259 0.692174 11.00000 -1.20000 H6B 2 0.366817 0.272017 0.696894 11.00000 -1.20000 AFIX 0 N7 3 0.362346 0.391033 0.784437 11.00000 0.07899 0.03870 = 0.08363 -0.00431 0.03121 -0.00888 H7 2 0.418583 0.348014 0.806502 11.00000 -1.20000 C8 1 0.345430 0.601125 0.813460 11.00000 0.05013 0.04341 = 0.07227 0.00014 0.01872 -0.00068 AFIX 13 H8 2 0.282455 0.643413 0.791573 11.00000 -1.20000 AFIX 0 C9 1 0.351755 0.585453 0.886667 11.00000 0.05160 0.04587 = 0.07535 0.00034 0.02312 -0.00293 C10 1 0.385313 0.401382 0.925113 11.00000 0.07934 0.04543 = 0.08626 0.00258 0.03653 0.00555 AFIX 43 H10 2 0.404897 0.279818 0.905240 11.00000 -1.20000 AFIX 0 C11 1 0.390267 0.394747 0.992243 11.00000 0.07835 0.04769 = 0.08555 0.01117 0.03220 0.00667 AFIX 43 H11 2 0.413164 0.269202 1.016579 11.00000 -1.20000 AFIX 0 C12 1 0.361534 0.572946 1.023971 11.00000 0.05186 0.05492 = 0.07326 0.00553 0.02070 0.00154 C13 1 0.363769 0.567772 1.095558 11.00000 0.04834 0.06286 = 0.07476 0.00962 0.02113 0.00523 C14 1 0.394655 0.745736 1.136537 11.00000 0.06705 0.06976 = 0.07708 0.00737 0.02309 -0.00212 AFIX 43 H14 2 0.413552 0.872444 1.118635 11.00000 -1.20000 AFIX 0 C15 1 0.398330 0.741231 1.203358 11.00000 0.07430 0.08969 = 0.07444 -0.00207 0.02024 0.00924 AFIX 43 H15 2 0.420181 0.862790 1.229986 11.00000 -1.20000 AFIX 0 C16 1 0.369577 0.556504 1.230195 11.00000 0.07225 0.10357 = 0.07707 0.01596 0.03129 0.01996 AFIX 43 H16 2 0.371764 0.552277 1.275131 11.00000 -1.20000 AFIX 0 C17 1 0.631839 0.791638 0.602732 11.00000 0.05358 0.09705 = 0.06217 -0.00765 0.01212 0.00753 AFIX 43 H17 2 0.692468 0.746434 0.612067 11.00000 -1.20000 AFIX 0 C18 1 0.568112 0.662306 0.621708 11.00000 0.06813 0.06044 = 0.05784 0.00231 0.01334 0.01316 AFIX 43 H18 2 0.586172 0.529756 0.643729 11.00000 -1.20000 AFIX 0 C19 1 0.330193 0.758697 0.985953 11.00000 0.07060 0.05545 = 0.07536 -0.00089 0.02124 0.01395 AFIX 43 H19 2 0.312168 0.881975 1.005982 11.00000 -1.20000 AFIX 0 C20 1 0.325251 0.764102 0.919144 11.00000 0.07518 0.05194 = 0.07512 0.00655 0.02128 0.01565 AFIX 43 H20 2 0.303552 0.890968 0.895076 11.00000 -1.20000 AFIX 0 C21 1 0.337513 0.377600 1.190461 11.00000 0.07989 0.08782 = 0.09817 0.03141 0.04253 0.00950 AFIX 43 H21 2 0.317524 0.252846 1.208630 11.00000 -1.20000 AFIX 0 C22 1 0.334713 0.381422 1.123814 11.00000 0.06989 0.06717 = 0.08861 0.00962 0.02976 -0.00330 AFIX 43 H22 2 0.313291 0.258832 1.097536 11.00000 -1.20000 AFIX 0 C23 1 0.406949 0.781978 0.797856 11.00000 0.07174 0.03850 = 0.07277 -0.00694 0.02672 -0.00653 AFIX 23 H23A 2 0.389357 0.923437 0.812586 11.00000 -1.20000 H23B 2 0.469735 0.753024 0.821811 11.00000 -1.20000 AFIX 0 C24 1 0.400021 0.792228 0.724178 11.00000 0.06048 0.03774 = 0.07196 -0.00213 0.02022 -0.00263 AFIX 23 H24A 2 0.339307 0.840882 0.700720 11.00000 -1.20000 H24B 2 0.443620 0.898955 0.716020 11.00000 -1.20000 AFIX 0 C25 1 1.098837 0.013276 0.963467 11.00000 0.09794 0.11663 = 0.06703 0.01617 0.02371 0.03007 AFIX 43 H25 2 1.144053 -0.071301 0.991363 11.00000 -1.20000 AFIX 0 C26 1 1.120964 0.208517 0.938318 11.00000 0.06503 0.13922 = 0.07338 -0.00712 0.01619 -0.00453 AFIX 43 H26 2 1.181354 0.256026 0.949053 11.00000 -1.20000 AFIX 0 C27 1 1.053195 0.336822 0.896571 11.00000 0.07959 0.08539 = 0.06009 -0.00026 0.02233 -0.01388 AFIX 43 H27 2 1.068722 0.469453 0.879790 11.00000 -1.20000 AFIX 0 C28 1 0.964164 0.268241 0.880283 11.00000 0.07241 0.05464 = 0.04797 -0.00482 0.01752 0.00127 C29 1 0.890538 0.400528 0.833677 11.00000 0.08207 0.05983 = 0.05982 -0.00628 0.01925 0.00877 AFIX 23 H29A 2 0.831158 0.345195 0.835472 11.00000 -1.20000 H29B 2 0.894835 0.553748 0.847766 11.00000 -1.20000 AFIX 0 C30 1 0.878913 0.165537 0.738023 11.00000 0.06398 0.04106 = 0.06353 -0.00141 0.01691 -0.00272 AFIX 23 H30A 2 0.816642 0.126092 0.737333 11.00000 -1.20000 H30B 2 0.919494 0.060123 0.765988 11.00000 -1.20000 AFIX 0 C31 1 0.891086 0.155034 0.668512 11.00000 0.07499 0.03870 = 0.05903 -0.00206 0.01919 0.00190 AFIX 23 H31A 2 0.872500 0.010595 0.649690 11.00000 -1.20000 H31B 2 0.955091 0.175038 0.670024 11.00000 -1.20000 AFIX 0 C32 1 0.834864 0.332070 0.624631 11.00000 0.04913 0.04463 = 0.05903 -0.00479 0.01278 -0.00326 AFIX 13 H32 2 0.770589 0.294217 0.619702 11.00000 -1.20000 AFIX 0 C33 1 0.848527 0.342789 0.555053 11.00000 0.04653 0.04643 = 0.05907 -0.00162 0.01140 0.00058 C34 1 0.813410 0.512774 0.512999 11.00000 0.12325 0.07641 = 0.07584 0.01429 0.04788 0.05333 AFIX 43 H34 2 0.782322 0.625864 0.528020 11.00000 -1.20000 AFIX 0 C35 1 0.822720 0.521644 0.448797 11.00000 0.12613 0.07555 = 0.07343 0.01767 0.04159 0.04909 AFIX 43 H35 2 0.797166 0.640074 0.421999 11.00000 -1.20000 AFIX 0 C36 1 0.867671 0.364231 0.423530 11.00000 0.04424 0.04921 = 0.06178 -0.00127 0.01249 0.00276 C37 1 0.876524 0.372217 0.354065 11.00000 0.04045 0.05244 = 0.06245 0.00124 0.01311 0.00131 C38 1 0.848416 0.554026 0.313712 11.00000 0.06938 0.05908 = 0.07538 0.00583 0.02491 0.01412 AFIX 43 H38 2 0.824279 0.675353 0.330662 11.00000 -1.20000 AFIX 0 C39 1 0.855234 0.560311 0.248781 11.00000 0.07473 0.07590 = 0.07379 0.01911 0.02157 0.01081 AFIX 43 H39 2 0.835210 0.684106 0.222684 11.00000 -1.20000 AFIX 0 C40 1 0.891337 0.384876 0.223042 11.00000 0.05827 0.08907 = 0.06134 0.00090 0.01786 -0.00002 AFIX 43 H40 2 0.896963 0.389698 0.179722 11.00000 -1.20000 AFIX 0 C41 1 0.919243 0.201425 0.261637 11.00000 0.06558 0.07951 = 0.07041 -0.00645 0.02479 0.01029 AFIX 43 H41 2 0.943491 0.081163 0.244269 11.00000 -1.20000 AFIX 0 C42 1 0.911494 0.194550 0.326110 11.00000 0.06265 0.05956 = 0.06605 0.00245 0.01919 0.01047 AFIX 43 H42 2 0.930060 0.068361 0.351421 11.00000 -1.20000 AFIX 0 C43 1 0.904195 0.197704 0.465796 11.00000 0.20790 0.08649 = 0.07894 0.02134 0.06489 0.08269 AFIX 43 H43 2 0.936601 0.086958 0.450952 11.00000 -1.20000 AFIX 0 C44 1 0.895056 0.186381 0.530172 11.00000 0.20606 0.07674 = 0.07604 0.02091 0.05518 0.07168 AFIX 43 H44 2 0.921422 0.068805 0.557036 11.00000 -1.20000 AFIX 0 C45 1 0.838161 0.544265 0.722773 11.00000 0.07804 0.04840 = 0.06323 -0.00506 0.01435 0.01264 AFIX 23 H45A 2 0.775458 0.505980 0.721097 11.00000 -1.20000 H45B 2 0.849803 0.690636 0.742026 11.00000 -1.20000 AFIX 0 C46 1 0.943768 0.070467 0.906363 11.00000 0.08421 0.06104 = 0.05969 -0.00250 0.02112 -0.00452 AFIX 43 H46 2 0.883537 0.021834 0.895901 11.00000 -1.20000 AFIX 0 C47 1 1.010533 -0.056704 0.947546 11.00000 0.11156 0.07139 = 0.06632 0.00801 0.03121 0.01347 AFIX 43 H47 2 0.995223 -0.189557 0.964324 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_TP_CY001_0ma_a.res in P2(1) REM R1 = 0.0457 for 5814 Fo > 4sig(Fo) and 0.0513 for all 6569 data REM 454 parameters refined using 1 restraints END WGHT 0.0770 0.1019 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.217, deepest hole -0.243, 1-sigma level 0.040 Q1 1 0.8403 0.1735 0.4524 11.00000 0.05 0.22 Q2 1 0.8305 0.1620 0.5238 11.00000 0.05 0.20 Q3 1 0.8476 0.7006 0.5457 11.00000 0.05 0.16 Q4 1 0.8805 0.5438 0.4692 11.00000 0.05 0.15 Q5 1 0.8655 0.5239 0.5405 11.00000 0.05 0.15 Q6 1 0.8699 -0.0075 0.4259 11.00000 0.05 0.13 Q7 1 0.9229 0.2507 0.4676 11.00000 0.05 0.13 Q8 1 0.8800 0.8311 0.4251 11.00000 0.05 0.13 Q9 1 0.3666 0.2282 0.8805 11.00000 0.05 0.12 Q10 1 0.9256 0.3990 0.1588 11.00000 0.05 0.12 Q11 1 0.3949 0.2307 0.6938 11.00000 0.05 0.11 Q12 1 0.9163 0.2240 0.5392 11.00000 0.05 0.11 Q13 1 0.9221 0.5880 0.3650 11.00000 0.05 0.11 Q14 1 0.8878 0.7084 0.7494 11.00000 0.05 0.11 Q15 1 0.9362 0.6462 0.1826 11.00000 0.05 0.11 Q16 1 0.4331 0.2985 0.6543 11.00000 0.05 0.11 Q17 1 0.9372 0.7244 0.4007 11.00000 0.05 0.11 Q18 1 0.8413 -0.0279 0.5385 11.00000 0.05 0.11 Q19 1 0.3418 0.1842 1.0687 11.00000 0.05 0.10 Q20 1 0.8774 0.7884 0.3580 11.00000 0.05 0.10 ; _shelx_res_checksum 69802 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 N1 N 0.41820(15) 0.5764(3) 0.69912(11) 0.0553(5) Uani 1 1 d . . . . . N2 N 0.89882(14) 0.3872(3) 0.76535(10) 0.0537(5) Uani 1 1 d . . . . . N3 N 0.84908(16) 0.5497(4) 0.65582(10) 0.0566(5) Uani 1 1 d . . . . . H3A H 0.8991 0.6117 0.6533 0.068 Uiso 1 1 d R U . . . C1 C 0.6056(2) 0.9881(6) 0.56989(14) 0.0707(8) Uani 1 1 d . . . . . H1 H 0.6484 1.0740 0.5563 0.085 Uiso 1 1 calc R U . . . C2 C 0.5169(2) 1.0569(5) 0.55729(14) 0.0677(7) Uani 1 1 d . . . . . H2 H 0.4994 1.1909 0.5360 0.081 Uiso 1 1 calc R U . . . C3 C 0.45369(19) 0.9267(5) 0.57630(14) 0.0617(7) Uani 1 1 d . . . . . H3 H 0.3933 0.9738 0.5674 0.074 Uiso 1 1 calc R U . . . C4 C 0.47783(18) 0.7268(4) 0.60848(12) 0.0557(6) Uani 1 1 d . . . . . C5 C 0.4080(2) 0.5825(5) 0.62768(14) 0.0670(7) Uani 1 1 d . . . . . H5A H 0.3474 0.6364 0.6059 0.080 Uiso 1 1 calc R U . . . H5B H 0.4133 0.4334 0.6120 0.080 Uiso 1 1 calc R U . . . C6 C 0.3553(2) 0.4144(5) 0.71447(16) 0.0693(8) Uani 1 1 d . . . . . H6A H 0.2933 0.4573 0.6922 0.083 Uiso 1 1 calc R U . . . H6B H 0.3668 0.2720 0.6969 0.083 Uiso 1 1 calc R U . . . N7 N 0.36235(19) 0.3910(4) 0.78444(13) 0.0652(6) Uani 1 1 d . . . . . H7 H 0.419(2) 0.348(6) 0.8065(16) 0.078 Uiso 1 1 d . U . . . C8 C 0.34543(17) 0.6011(4) 0.81346(14) 0.0547(6) Uani 1 1 d . . . . . H8 H 0.2825 0.6434 0.7916 0.066 Uiso 1 1 calc R U . . . C9 C 0.35175(17) 0.5855(4) 0.88667(14) 0.0564(6) Uani 1 1 d . . . . . C10 C 0.3853(2) 0.4014(5) 0.92511(15) 0.0675(7) Uani 1 1 d . . . . . H10 H 0.4049 0.2798 0.9052 0.081 Uiso 1 1 calc R U . . . C11 C 0.3903(2) 0.3947(5) 0.99224(16) 0.0685(7) Uani 1 1 d . . . . . H11 H 0.4132 0.2692 1.0166 0.082 Uiso 1 1 calc R U . . . C12 C 0.36153(17) 0.5729(5) 1.02397(14) 0.0592(6) Uani 1 1 d . . . . . C13 C 0.36377(17) 0.5678(5) 1.09556(14) 0.0610(6) Uani 1 1 d . . . . . C14 C 0.3947(2) 0.7457(6) 1.13654(15) 0.0705(8) Uani 1 1 d . . . . . H14 H 0.4136 0.8724 1.1186 0.085 Uiso 1 1 calc R U . . . C15 C 0.3983(2) 0.7412(7) 1.20336(16) 0.0793(9) Uani 1 1 d . . . . . H15 H 0.4202 0.8628 1.2300 0.095 Uiso 1 1 calc R U . . . C16 C 0.3696(2) 0.5565(7) 1.23019(17) 0.0821(10) Uani 1 1 d . . . . . H16 H 0.3718 0.5523 1.2751 0.098 Uiso 1 1 calc R U . . . C17 C 0.6318(2) 0.7916(6) 0.60273(14) 0.0714(8) Uani 1 1 d . . . . . H17 H 0.6925 0.7464 0.6121 0.086 Uiso 1 1 calc R U . . . C18 C 0.56811(19) 0.6623(5) 0.62171(13) 0.0627(7) Uani 1 1 d . . . . . H18 H 0.5862 0.5298 0.6437 0.075 Uiso 1 1 calc R U . . . C19 C 0.3302(2) 0.7587(5) 0.98595(14) 0.0667(7) Uani 1 1 d . . . . . H19 H 0.3122 0.8820 1.0060 0.080 Uiso 1 1 calc R U . . . C20 C 0.3253(2) 0.7641(5) 0.91914(15) 0.0671(7) Uani 1 1 d . . . . . H20 H 0.3036 0.8910 0.8951 0.080 Uiso 1 1 calc R U . . . C21 C 0.3375(2) 0.3776(7) 1.19046(19) 0.0850(10) Uani 1 1 d . . . . . H21 H 0.3175 0.2528 1.2086 0.102 Uiso 1 1 calc R U . . . C22 C 0.3347(2) 0.3814(6) 1.12381(17) 0.0735(8) Uani 1 1 d . . . . . H22 H 0.3133 0.2588 1.0975 0.088 Uiso 1 1 calc R U . . . C23 C 0.4069(2) 0.7820(4) 0.79786(14) 0.0595(6) Uani 1 1 d . . . . . H23A H 0.3894 0.9234 0.8126 0.071 Uiso 1 1 calc R U . . . H23B H 0.4697 0.7530 0.8218 0.071 Uiso 1 1 calc R U . . . C24 C 0.40002(19) 0.7922(4) 0.72418(13) 0.0561(6) Uani 1 1 d . . . . . H24A H 0.3393 0.8409 0.7007 0.067 Uiso 1 1 calc R U . . . H24B H 0.4436 0.8990 0.7160 0.067 Uiso 1 1 calc R U . . . C25 C 1.0988(3) 0.0133(8) 0.96347(17) 0.0934(12) Uani 1 1 d . . . . . H25 H 1.1441 -0.0713 0.9914 0.112 Uiso 1 1 calc R U . . . C26 C 1.1210(2) 0.2085(9) 0.93832(17) 0.0928(12) Uani 1 1 d . . . . . H26 H 1.1814 0.2560 0.9491 0.111 Uiso 1 1 calc R U . . . C27 C 1.0532(2) 0.3368(6) 0.89657(14) 0.0742(8) Uani 1 1 d . . . . . H27 H 1.0687 0.4695 0.8798 0.089 Uiso 1 1 calc R U . . . C28 C 0.96416(19) 0.2682(5) 0.88028(12) 0.0580(6) Uani 1 1 d . . . . . C29 C 0.8905(2) 0.4005(5) 0.83368(13) 0.0671(7) Uani 1 1 d . . . . . H29A H 0.8312 0.3452 0.8355 0.080 Uiso 1 1 calc R U . . . H29B H 0.8948 0.5537 0.8478 0.080 Uiso 1 1 calc R U . . . C30 C 0.87891(19) 0.1655(4) 0.73802(13) 0.0561(6) Uani 1 1 d . . . . . H30A H 0.8166 0.1261 0.7373 0.067 Uiso 1 1 calc R U . . . H30B H 0.9195 0.0601 0.7660 0.067 Uiso 1 1 calc R U . . . C31 C 0.8911(2) 0.1550(4) 0.66851(12) 0.0572(6) Uani 1 1 d . . . . . H31A H 0.8725 0.0106 0.6497 0.069 Uiso 1 1 calc R U . . . H31B H 0.9551 0.1750 0.6700 0.069 Uiso 1 1 calc R U . . . C32 C 0.83486(17) 0.3321(4) 0.62463(12) 0.0511(6) Uani 1 1 d . . . . . H32 H 0.7706 0.2942 0.6197 0.061 Uiso 1 1 calc R U . . . C33 C 0.84853(16) 0.3428(4) 0.55505(12) 0.0511(6) Uani 1 1 d . . . . . C34 C 0.8134(3) 0.5128(6) 0.51300(16) 0.0877(11) Uani 1 1 d . . . . . H34 H 0.7823 0.6259 0.5280 0.105 Uiso 1 1 calc R U . . . C35 C 0.8227(3) 0.5216(6) 0.44880(16) 0.0888(11) Uani 1 1 d . . . . . H35 H 0.7972 0.6401 0.4220 0.107 Uiso 1 1 calc R U . . . C36 C 0.86767(16) 0.3642(4) 0.42353(12) 0.0520(6) Uani 1 1 d . . . . . C37 C 0.87652(15) 0.3722(4) 0.35406(12) 0.0518(6) Uani 1 1 d . . . . . C38 C 0.8484(2) 0.5540(5) 0.31371(15) 0.0668(7) Uani 1 1 d . . . . . H38 H 0.8243 0.6754 0.3307 0.080 Uiso 1 1 calc R U . . . C39 C 0.8552(2) 0.5603(6) 0.24878(16) 0.0744(8) Uani 1 1 d . . . . . H39 H 0.8352 0.6841 0.2227 0.089 Uiso 1 1 calc R U . . . C40 C 0.89134(19) 0.3849(6) 0.22304(14) 0.0691(8) Uani 1 1 d . . . . . H40 H 0.8970 0.3897 0.1797 0.083 Uiso 1 1 calc R U . . . C41 C 0.9192(2) 0.2014(6) 0.26164(14) 0.0705(8) Uani 1 1 d . . . . . H41 H 0.9435 0.0812 0.2443 0.085 Uiso 1 1 calc R U . . . C42 C 0.91149(19) 0.1946(5) 0.32611(14) 0.0623(7) Uani 1 1 d . . . . . H42 H 0.9301 0.0684 0.3514 0.075 Uiso 1 1 calc R U . . . C43 C 0.9042(4) 0.1977(7) 0.46580(18) 0.1193(18) Uani 1 1 d . . . . . H43 H 0.9366 0.0870 0.4510 0.143 Uiso 1 1 calc R U . . . C44 C 0.8951(4) 0.1864(7) 0.53017(19) 0.1162(18) Uani 1 1 d . . . . . H44 H 0.9214 0.0688 0.5570 0.139 Uiso 1 1 calc R U . . . C45 C 0.8382(2) 0.5443(5) 0.72277(14) 0.0639(7) Uani 1 1 d . . . . . H45A H 0.7755 0.5060 0.7211 0.077 Uiso 1 1 calc R U . . . H45B H 0.8498 0.6906 0.7420 0.077 Uiso 1 1 calc R U . . . C46 C 0.9438(2) 0.0705(5) 0.90636(14) 0.0678(7) Uani 1 1 d . . . . . H46 H 0.8835 0.0218 0.8959 0.081 Uiso 1 1 calc R U . . . C47 C 1.0105(3) -0.0567(6) 0.94755(15) 0.0816(9) Uani 1 1 d . . . . . H47 H 0.9952 -0.1896 0.9643 0.098 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 0.0624(12) 0.0384(10) 0.0678(13) -0.0045(10) 0.0217(10) -0.0041(9) N2 0.0645(12) 0.0403(10) 0.0541(11) -0.0024(9) 0.0116(9) 0.0014(10) N3 0.0660(13) 0.0409(10) 0.0607(12) -0.0013(9) 0.0124(10) 0.0058(10) C1 0.0697(18) 0.084(2) 0.0583(15) -0.0087(14) 0.0166(13) -0.0196(16) C2 0.088(2) 0.0544(15) 0.0603(15) 0.0003(13) 0.0190(13) -0.0017(15) C3 0.0597(15) 0.0607(16) 0.0637(15) -0.0018(12) 0.0140(12) 0.0106(12) C4 0.0629(15) 0.0509(14) 0.0545(13) -0.0071(11) 0.0172(11) 0.0019(12) C5 0.0759(18) 0.0571(15) 0.0692(17) -0.0102(14) 0.0207(13) -0.0083(14) C6 0.0841(19) 0.0448(14) 0.084(2) -0.0116(13) 0.0312(15) -0.0162(14) N7 0.0790(15) 0.0387(11) 0.0836(16) -0.0043(11) 0.0312(12) -0.0089(11) C8 0.0501(12) 0.0434(13) 0.0723(16) 0.0001(11) 0.0187(11) -0.0007(10) C9 0.0516(13) 0.0459(13) 0.0754(16) 0.0003(12) 0.0231(11) -0.0029(11) C10 0.0793(18) 0.0454(14) 0.086(2) 0.0026(14) 0.0365(15) 0.0056(14) C11 0.0783(18) 0.0477(15) 0.086(2) 0.0112(14) 0.0322(15) 0.0067(14) C12 0.0519(13) 0.0549(14) 0.0733(16) 0.0055(13) 0.0207(11) 0.0015(12) C13 0.0483(13) 0.0629(16) 0.0748(17) 0.0096(14) 0.0211(12) 0.0052(13) C14 0.0670(17) 0.0698(19) 0.0771(18) 0.0074(16) 0.0231(14) -0.0021(15) C15 0.0743(19) 0.090(2) 0.0744(19) -0.0021(18) 0.0202(15) 0.0092(18) C16 0.0722(19) 0.104(3) 0.077(2) 0.016(2) 0.0313(16) 0.020(2) C17 0.0536(14) 0.097(2) 0.0622(15) -0.0077(16) 0.0121(12) 0.0075(15) C18 0.0681(17) 0.0604(16) 0.0578(15) 0.0023(12) 0.0133(12) 0.0132(13) C19 0.0706(17) 0.0554(16) 0.0754(17) -0.0009(14) 0.0212(13) 0.0140(14) C20 0.0752(18) 0.0519(15) 0.0751(17) 0.0066(14) 0.0213(14) 0.0156(13) C21 0.080(2) 0.088(2) 0.098(2) 0.031(2) 0.0425(19) 0.010(2) C22 0.0699(17) 0.0672(18) 0.089(2) 0.0096(16) 0.0298(15) -0.0033(15) C23 0.0717(16) 0.0385(12) 0.0728(16) -0.0069(12) 0.0267(13) -0.0065(12) C24 0.0605(14) 0.0377(12) 0.0720(16) -0.0021(11) 0.0202(12) -0.0026(11) C25 0.098(3) 0.117(3) 0.0670(19) 0.016(2) 0.0237(18) 0.030(2) C26 0.0650(19) 0.139(4) 0.073(2) -0.007(2) 0.0162(15) -0.005(2) C27 0.0796(19) 0.085(2) 0.0601(16) -0.0003(15) 0.0223(14) -0.0139(17) C28 0.0724(16) 0.0546(14) 0.0480(13) -0.0048(11) 0.0175(11) 0.0013(12) C29 0.0821(19) 0.0598(16) 0.0598(15) -0.0063(13) 0.0193(13) 0.0088(15) C30 0.0640(15) 0.0411(12) 0.0635(15) -0.0014(11) 0.0169(12) -0.0027(11) C31 0.0750(17) 0.0387(12) 0.0590(15) -0.0021(11) 0.0192(12) 0.0019(12) C32 0.0491(12) 0.0446(13) 0.0590(14) -0.0048(11) 0.0128(10) -0.0033(10) C33 0.0465(12) 0.0464(13) 0.0591(14) -0.0016(11) 0.0114(10) 0.0006(10) C34 0.123(3) 0.076(2) 0.0758(19) 0.0143(16) 0.0479(19) 0.053(2) C35 0.126(3) 0.076(2) 0.0734(19) 0.0177(16) 0.0416(19) 0.049(2) C36 0.0442(11) 0.0492(13) 0.0618(14) -0.0013(11) 0.0125(10) 0.0028(11) C37 0.0405(11) 0.0524(14) 0.0625(14) 0.0012(12) 0.0131(10) 0.0013(11) C38 0.0694(16) 0.0591(16) 0.0754(18) 0.0058(14) 0.0249(13) 0.0141(15) C39 0.0747(18) 0.076(2) 0.0738(18) 0.0191(16) 0.0216(14) 0.0108(17) C40 0.0583(15) 0.089(2) 0.0613(16) 0.0009(15) 0.0179(12) 0.0000(16) C41 0.0656(17) 0.080(2) 0.0704(18) -0.0065(15) 0.0248(13) 0.0103(15) C42 0.0627(15) 0.0596(16) 0.0660(16) 0.0025(13) 0.0192(12) 0.0105(13) C43 0.208(5) 0.086(3) 0.079(2) 0.021(2) 0.065(3) 0.083(3) C44 0.206(5) 0.077(2) 0.076(2) 0.0209(18) 0.055(3) 0.072(3) C45 0.0780(17) 0.0484(14) 0.0632(15) -0.0051(12) 0.0144(13) 0.0126(13) C46 0.0842(19) 0.0610(16) 0.0597(15) -0.0025(13) 0.0211(13) -0.0045(15) C47 0.112(3) 0.0714(19) 0.0663(18) 0.0080(15) 0.0312(17) 0.0135(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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 C5 N1 C6 109.7(2) . . ? C5 N1 C24 111.3(2) . . ? C24 N1 C6 109.2(2) . . ? C30 N2 C29 111.7(2) . . ? C45 N2 C29 111.0(2) . . ? C45 N2 C30 109.1(2) . . ? C32 N3 H3A 113.5 . . ? C45 N3 H3A 112.9 . . ? C45 N3 C32 111.7(2) . . ? C2 C1 H1 120.0 . . ? C2 C1 C17 120.1(3) . . ? C17 C1 H1 120.0 . . ? C1 C2 H2 120.2 . . ? C1 C2 C3 119.6(3) . . ? C3 C2 H2 120.2 . . ? C2 C3 H3 119.2 . . ? C2 C3 C4 121.5(3) . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 121.3(3) . . ? C18 C4 C3 117.9(3) . . ? C18 C4 C5 120.8(3) . . ? N1 C5 C4 113.0(2) . . ? N1 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C4 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C6 H6A 108.8 . . ? N1 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? N7 C6 N1 113.9(2) . . ? N7 C6 H6A 108.8 . . ? N7 C6 H6B 108.8 . . ? C6 N7 H7 111(2) . . ? C6 N7 C8 111.1(2) . . ? C8 N7 H7 107(2) . . ? N7 C8 H8 106.8 . . ? N7 C8 C9 113.2(2) . . ? N7 C8 C23 110.7(2) . . ? C9 C8 H8 106.8 . . ? C9 C8 C23 112.2(2) . . ? C23 C8 H8 106.8 . . ? C10 C9 C8 123.6(2) . . ? C20 C9 C8 119.6(2) . . ? C20 C9 C10 116.8(3) . . ? C9 C10 H10 119.2 . . ? C11 C10 C9 121.6(3) . . ? C11 C10 H10 119.2 . . ? C10 C11 H11 119.4 . . ? C10 C11 C12 121.1(3) . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 122.2(3) . . ? C19 C12 C11 117.3(3) . . ? C19 C12 C13 120.5(3) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 C22 117.6(3) . . ? C22 C13 C12 120.9(3) . . ? C13 C14 H14 119.0 . . ? C13 C14 C15 121.9(3) . . ? C15 C14 H14 119.0 . . ? C14 C15 H15 120.2 . . ? C16 C15 C14 119.6(4) . . ? C16 C15 H15 120.2 . . ? C15 C16 H16 120.1 . . ? C15 C16 C21 119.8(3) . . ? C21 C16 H16 120.1 . . ? C1 C17 H17 120.0 . . ? C18 C17 C1 119.9(3) . . ? C18 C17 H17 120.0 . . ? C4 C18 H18 119.5 . . ? C17 C18 C4 120.9(3) . . ? C17 C18 H18 119.5 . . ? C12 C19 H19 119.4 . . ? C20 C19 C12 121.3(3) . . ? C20 C19 H19 119.4 . . ? C9 C20 H20 119.1 . . ? C19 C20 C9 121.9(3) . . ? C19 C20 H20 119.1 . . ? C16 C21 H21 119.7 . . ? C16 C21 C22 120.6(3) . . ? C22 C21 H21 119.7 . . ? C13 C22 H22 119.7 . . ? C21 C22 C13 120.5(3) . . ? C21 C22 H22 119.7 . . ? C8 C23 H23A 109.4 . . ? C8 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C24 C23 C8 111.1(2) . . ? C24 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? N1 C24 C23 110.9(2) . . ? N1 C24 H24A 109.5 . . ? N1 C24 H24B 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? C26 C25 H25 120.1 . . ? C47 C25 H25 120.1 . . ? C47 C25 C26 119.8(4) . . ? C25 C26 H26 119.8 . . ? C25 C26 C27 120.3(4) . . ? C27 C26 H26 119.8 . . ? C26 C27 H27 119.8 . . ? C28 C27 C26 120.3(3) . . ? C28 C27 H27 119.8 . . ? C27 C28 C29 121.2(3) . . ? C27 C28 C46 118.1(3) . . ? C46 C28 C29 120.7(3) . . ? N2 C29 C28 111.3(2) . . ? N2 C29 H29A 109.4 . . ? N2 C29 H29B 109.4 . . ? C28 C29 H29A 109.4 . . ? C28 C29 H29B 109.4 . . ? H29A C29 H29B 108.0 . . ? N2 C30 H30A 109.6 . . ? N2 C30 H30B 109.6 . . ? N2 C30 C31 110.5(2) . . ? H30A C30 H30B 108.1 . . ? C31 C30 H30A 109.6 . . ? C31 C30 H30B 109.6 . . ? C30 C31 H31A 109.4 . . ? C30 C31 H31B 109.4 . . ? C30 C31 C32 111.1(2) . . ? H31A C31 H31B 108.0 . . ? C32 C31 H31A 109.4 . . ? C32 C31 H31B 109.4 . . ? N3 C32 C31 111.84(19) . . ? N3 C32 H32 106.6 . . ? N3 C32 C33 110.3(2) . . ? C31 C32 H32 106.6 . . ? C33 C32 C31 114.3(2) . . ? C33 C32 H32 106.6 . . ? C34 C33 C32 121.2(2) . . ? C44 C33 C32 123.1(2) . . ? C44 C33 C34 115.6(3) . . ? C33 C34 H34 119.0 . . ? C33 C34 C35 122.0(3) . . ? C35 C34 H34 119.0 . . ? C34 C35 H35 118.8 . . ? C36 C35 C34 122.4(3) . . ? C36 C35 H35 118.8 . . ? C35 C36 C37 122.4(2) . . ? C35 C36 C43 115.5(3) . . ? C43 C36 C37 122.1(2) . . ? C38 C37 C36 121.8(2) . . ? C38 C37 C42 116.7(2) . . ? C42 C37 C36 121.5(2) . . ? C37 C38 H38 119.1 . . ? C37 C38 C39 121.9(3) . . ? C39 C38 H38 119.1 . . ? C38 C39 H39 120.0 . . ? C40 C39 C38 120.1(3) . . ? C40 C39 H39 120.0 . . ? C39 C40 H40 120.3 . . ? C39 C40 C41 119.5(3) . . ? C41 C40 H40 120.3 . . ? C40 C41 H41 119.8 . . ? C40 C41 C42 120.3(3) . . ? C42 C41 H41 119.8 . . ? C37 C42 H42 119.3 . . ? C41 C42 C37 121.5(3) . . ? C41 C42 H42 119.3 . . ? C36 C43 H43 118.7 . . ? C36 C43 C44 122.6(3) . . ? C44 C43 H43 118.7 . . ? C33 C44 C43 121.7(3) . . ? C33 C44 H44 119.1 . . ? C43 C44 H44 119.1 . . ? N2 C45 H45A 109.0 . . ? N2 C45 H45B 109.0 . . ? N3 C45 N2 113.1(2) . . ? N3 C45 H45A 109.0 . . ? N3 C45 H45B 109.0 . . ? H45A C45 H45B 107.8 . . ? C28 C46 H46 119.2 . . ? C47 C46 C28 121.7(3) . . ? C47 C46 H46 119.2 . . ? C25 C47 C46 119.7(4) . . ? C25 C47 H47 120.2 . . ? C46 C47 H47 120.2 . . ? 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 C5 1.459(3) . ? N1 C6 1.460(4) . ? N1 C24 1.459(3) . ? N2 C29 1.465(3) . ? N2 C30 1.459(3) . ? N2 C45 1.455(3) . ? N3 H3A 0.8601 . ? N3 C32 1.460(3) . ? N3 C45 1.449(3) . ? C1 H1 0.9300 . ? C1 C2 1.367(5) . ? C1 C17 1.379(5) . ? C2 H2 0.9300 . ? C2 C3 1.376(4) . ? C3 H3 0.9300 . ? C3 C4 1.386(4) . ? C4 C5 1.504(4) . ? C4 C18 1.381(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 N7 1.443(4) . ? N7 H7 0.90(3) . ? N7 C8 1.459(3) . ? C8 H8 0.9800 . ? C8 C9 1.509(4) . ? C8 C23 1.526(4) . ? C9 C10 1.390(4) . ? C9 C20 1.389(4) . ? C10 H10 0.9300 . ? C10 C11 1.384(4) . ? C11 H11 0.9300 . ? C11 C12 1.393(4) . ? C12 C13 1.486(4) . ? C12 C19 1.387(4) . ? C13 C14 1.380(5) . ? C13 C22 1.396(4) . ? C14 H14 0.9300 . ? C14 C15 1.381(4) . ? C15 H15 0.9300 . ? C15 C16 1.371(6) . ? C16 H16 0.9300 . ? C16 C21 1.374(6) . ? C17 H17 0.9300 . ? C17 C18 1.378(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C19 C20 1.377(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C21 C22 1.380(5) . ? C22 H22 0.9300 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 C24 1.515(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25 0.9300 . ? C25 C26 1.369(7) . ? C25 C47 1.361(6) . ? C26 H26 0.9300 . ? C26 C27 1.398(5) . ? C27 H27 0.9300 . ? C27 C28 1.368(4) . ? C28 C29 1.508(4) . ? C28 C46 1.383(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 C31 1.510(4) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.520(4) . ? C32 H32 0.9800 . ? C32 C33 1.520(3) . ? C33 C34 1.368(4) . ? C33 C44 1.361(4) . ? C34 H34 0.9300 . ? C34 C35 1.384(4) . ? C35 H35 0.9300 . ? C35 C36 1.355(4) . ? C36 C37 1.490(3) . ? C36 C43 1.360(4) . ? C37 C38 1.384(4) . ? C37 C42 1.392(4) . ? C38 H38 0.9300 . ? C38 C39 1.386(4) . ? C39 H39 0.9300 . ? C39 C40 1.366(5) . ? C40 H40 0.9300 . ? C40 C41 1.373(5) . ? C41 H41 0.9300 . ? C41 C42 1.381(4) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C43 C44 1.387(5) . ? C44 H44 0.9300 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46 0.9300 . ? C46 C47 1.381(5) . ? C47 H47 0.9300 . ? 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 N1 C6 N7 C8 58.5(3) . . . . ? N2 C30 C31 C32 -54.1(3) . . . . ? N3 C32 C33 C34 -43.3(4) . . . . ? N3 C32 C33 C44 137.2(4) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C1 C17 C18 C4 -0.2(4) . . . . ? C2 C1 C17 C18 1.3(4) . . . . ? C2 C3 C4 C5 -178.5(2) . . . . ? C2 C3 C4 C18 0.7(4) . . . . ? C3 C4 C5 N1 -109.2(3) . . . . ? C3 C4 C18 C17 -0.8(4) . . . . ? C5 N1 C6 N7 178.1(2) . . . . ? C5 N1 C24 C23 177.6(2) . . . . ? C5 C4 C18 C17 178.4(3) . . . . ? C6 N1 C5 C4 -173.5(3) . . . . ? C6 N1 C24 C23 56.4(3) . . . . ? C6 N7 C8 C9 179.8(2) . . . . ? C6 N7 C8 C23 -53.2(3) . . . . ? N7 C8 C9 C10 10.4(4) . . . . ? N7 C8 C9 C20 -171.3(3) . . . . ? N7 C8 C23 C24 51.9(3) . . . . ? C8 C9 C10 C11 179.7(3) . . . . ? C8 C9 C20 C19 -179.6(3) . . . . ? C8 C23 C24 N1 -54.1(3) . . . . ? C9 C8 C23 C24 179.4(2) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C9 C20 C19 -1.2(4) . . . . ? C10 C11 C12 C13 178.3(3) . . . . ? C10 C11 C12 C19 -1.7(4) . . . . ? C11 C12 C13 C14 136.4(3) . . . . ? C11 C12 C13 C22 -43.4(4) . . . . ? C11 C12 C19 C20 1.8(4) . . . . ? C12 C13 C14 C15 -179.0(3) . . . . ? C12 C13 C22 C21 179.6(3) . . . . ? C12 C19 C20 C9 -0.4(5) . . . . ? C13 C12 C19 C20 -178.2(3) . . . . ? C13 C14 C15 C16 -0.8(5) . . . . ? C14 C13 C22 C21 -0.2(4) . . . . ? C14 C15 C16 C21 0.1(5) . . . . ? C15 C16 C21 C22 0.6(5) . . . . ? C16 C21 C22 C13 -0.5(5) . . . . ? C17 C1 C2 C3 -1.4(4) . . . . ? C18 C4 C5 N1 71.6(3) . . . . ? C19 C12 C13 C14 -43.6(4) . . . . ? C19 C12 C13 C22 136.6(3) . . . . ? C20 C9 C10 C11 1.3(4) . . . . ? C22 C13 C14 C15 0.9(4) . . . . ? C23 C8 C9 C10 -115.8(3) . . . . ? C23 C8 C9 C20 62.5(3) . . . . ? C24 N1 C5 C4 65.5(3) . . . . ? C24 N1 C6 N7 -59.7(3) . . . . ? C25 C26 C27 C28 -0.2(5) . . . . ? C26 C25 C47 C46 -0.3(6) . . . . ? C26 C27 C28 C29 -178.1(3) . . . . ? C26 C27 C28 C46 0.2(4) . . . . ? C27 C28 C29 N2 71.2(3) . . . . ? C27 C28 C46 C47 -0.2(4) . . . . ? C28 C46 C47 C25 0.3(5) . . . . ? C29 N2 C30 C31 -178.1(2) . . . . ? C29 N2 C45 N3 175.4(2) . . . . ? C29 C28 C46 C47 178.0(3) . . . . ? C30 N2 C29 C28 67.8(3) . . . . ? C30 N2 C45 N3 -61.0(3) . . . . ? C30 C31 C32 N3 49.7(3) . . . . ? C30 C31 C32 C33 176.0(2) . . . . ? C31 C32 C33 C34 -170.3(3) . . . . ? C31 C32 C33 C44 10.2(4) . . . . ? C32 N3 C45 N2 57.1(3) . . . . ? C32 C33 C34 C35 -177.9(3) . . . . ? C32 C33 C44 C43 178.2(4) . . . . ? C33 C34 C35 C36 -0.5(7) . . . . ? C34 C33 C44 C43 -1.3(7) . . . . ? C34 C35 C36 C37 179.1(3) . . . . ? C34 C35 C36 C43 -0.8(6) . . . . ? C35 C36 C37 C38 7.6(4) . . . . ? C35 C36 C37 C42 -170.8(3) . . . . ? C35 C36 C43 C44 1.1(7) . . . . ? C36 C37 C38 C39 -178.9(3) . . . . ? C36 C37 C42 C41 179.6(2) . . . . ? C36 C43 C44 C33 0.0(8) . . . . ? C37 C36 C43 C44 -178.8(4) . . . . ? C37 C38 C39 C40 -0.7(5) . . . . ? C38 C37 C42 C41 1.2(4) . . . . ? C38 C39 C40 C41 1.1(5) . . . . ? C39 C40 C41 C42 -0.4(5) . . . . ? C40 C41 C42 C37 -0.7(4) . . . . ? C42 C37 C38 C39 -0.5(4) . . . . ? C43 C36 C37 C38 -172.5(4) . . . . ? C43 C36 C37 C42 9.1(5) . . . . ? C44 C33 C34 C35 1.6(6) . . . . ? C45 N2 C29 C28 -170.1(2) . . . . ? C45 N2 C30 C31 58.7(3) . . . . ? C45 N3 C32 C31 -50.5(3) . . . . ? C45 N3 C32 C33 -178.96(19) . . . . ? C46 C28 C29 N2 -107.0(3) . . . . ? C47 C25 C26 C27 0.3(6) . . . . ?