#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:41:23 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270499 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158319.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_7158319 loop_ _publ_author_name 'Kozhemyakin, Grigory L.' 'Tyurin, Vladimir S.' 'Shkirdova, Alena O.' 'Belyaev, Evgeny S.' 'Kirinova, Ekaterina S.' 'Ponomarev, Gelii V.' 'Chistov, Alexey A.' 'Aralov, Andrey V.' 'Tafeenko, Victor A.' 'Zamilatskov, Ilya A.' _publ_section_title ; Carbene functionalization of porphyrinoids through tosylhydrazones. ; _journal_issue 42 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9199 _journal_page_last 9210 _journal_paper_doi 10.1039/d1ob01626a _journal_volume 19 _journal_year 2021 _chemical_absolute_configuration rm _chemical_formula_moiety 'C41 H42 N4 O3' _chemical_formula_sum 'C41 H42 N4 O3' _chemical_formula_weight 638.78 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2021-06-24 deposited with the CCDC. 2021-09-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.5160(10) _cell_length_b 19.977(3) _cell_length_c 30.800(10) _cell_measurement_reflns_used 985 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 40.5 _cell_measurement_theta_min 4.06 _cell_volume 3393.9(14) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 295 _diffrn_detector Pilatus100K _diffrn_detector_area_resol_mean 5.81 _diffrn_detector_type STOE _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type STOE _diffrn_radiation_collimation 'focusing mirrors' _diffrn_radiation_monochromator none _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54186 _diffrn_reflns_av_R_equivalents 0.1035 _diffrn_reflns_av_unetI/netI 0.1150 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 16576 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 59.996 _diffrn_reflns_theta_max 59.996 _diffrn_reflns_theta_min 4.427 _diffrn_source 'Cu GeniX 3D' _diffrn_source_current 0.600 _diffrn_source_power 0.030 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.627 _exptl_absorpt_correction_T_max 0.706 _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.250 _exptl_crystal_description needle _exptl_crystal_F_000 1360 _exptl_crystal_size_max .12 _exptl_crystal_size_mid .06 _exptl_crystal_size_min .04 _refine_diff_density_max 0.356 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.082 _refine_ls_abs_structure_details ; Flack x determined using 160 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 4.1(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.877 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 4491 _refine_ls_number_restraints 84 _refine_ls_restrained_S_all 0.882 _refine_ls_R_factor_all 0.3021 _refine_ls_R_factor_gt 0.1405 _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^)+(0.1882P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3317 _refine_ls_wR_factor_ref 0.4249 _reflns_Friedel_coverage 0.624 _reflns_Friedel_fraction_full 0.824 _reflns_Friedel_fraction_max 0.824 _reflns_number_gt 1204 _reflns_number_total 4491 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01626a2.cif _cod_data_source_block porf _cod_depositor_comments 'Adding full bibliography for 7158319.cif.' _cod_database_code 7158319 _shelx_shelxl_version_number 2016/6 _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 ; TITL shelxt_a.res in P2(1)2(1)2(1) shelx.res created by SHELXL-2016/6 at 13:15:31 on 22-Jun-2021 CELL 1.54186 5.5160 19.9770 30.8000 90.000 90.000 90.000 ZERR 4.00 0.0010 0.0030 0.0100 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 164 168 16 12 MERG 2 FMAP 2 omit -2 120 conf omit 0 0 2 omit 0 1 1 omit 1 0 2 omit 0 1 2 PLAN dfix 1.37 0.02 n1 c5 n1 c2 n2 c22 n2 c19 n3 c7 n3 c10 n4 c14 n4 c17 dfix 1.49 0.03 c16 c32 c15 c28 c28 c29 c29 c30 c8 c27 c4 c25 c25 c26 dfix 1.49 0.03 c3 c24 c21 c34 c34 c35 c35 c36 c20 c33 c15 c16 c14 c15 dfix 1.49 0.03 c34 c42 c35 c42 dfix 1.40 0.03 c2 c3 c22 c23 c18 c19 c17 c18 c14 c15 c7 c6 c6 c5 dfix 1.22 0.03 c30 o2 dfix 1.368 0.03 c30 o3 dfix 1.00 0.03 c34 h34 c16 h16 c35 h35 BOND $H htab HTAB N2 N1 HTAB N2 N4 HTAB N3 N1 HTAB C15 O2 EQIV $1 x+1, y, z HTAB C16 O2_$1 HTAB C29 O2_$1 LIST 4 eadp c37 c38 c39 c40 c41 c36 L.S. 10 acta isor .04 c41 c40 c39 c38 c37 c35 c34 c36 WGHT 0.188200 FVAR 0.39768 O1 4 -0.601901 0.118447 0.347753 11.00000 0.05807 0.11778 = 0.19678 0.03672 0.00885 -0.02551 O2 4 -0.273125 0.351234 0.471113 11.00000 0.01543 0.22418 = 0.14945 -0.01125 -0.03123 0.02181 O3 4 -0.058503 0.378524 0.529974 11.00000 0.08695 0.12464 = 0.14877 -0.01670 -0.00136 -0.00860 N1 3 0.276618 0.244228 0.190659 11.00000 0.03716 0.09517 = 0.13713 -0.01320 0.00405 0.02914 N2 3 0.541344 0.343245 0.246777 11.00000 0.01164 0.10520 = 0.11661 -0.02431 0.01163 -0.00642 AFIX 43 H2 2 0.419019 0.317085 0.250215 11.00000 -1.20000 AFIX 0 N3 3 -0.013956 0.209884 0.259928 11.00000 0.03441 0.09728 = 0.11199 -0.02644 0.01562 -0.00443 AFIX 43 H3 2 0.107616 0.234967 0.253530 11.00000 -1.20000 AFIX 0 N4 3 0.228450 0.304249 0.321361 11.00000 0.01840 0.09005 = 0.11516 -0.02368 0.01488 0.02011 C2 1 0.437541 0.264964 0.159865 11.00000 0.03394 0.08842 = 0.12206 -0.00080 -0.02140 0.01064 C3 1 0.415421 0.236932 0.119263 11.00000 0.04588 0.07533 = 0.13124 -0.01106 -0.00250 -0.01600 C4 1 0.229625 0.190435 0.124701 11.00000 0.07275 0.06068 = 0.13540 0.00007 -0.03702 0.03356 C5 1 0.137771 0.198219 0.167961 11.00000 0.05312 0.07429 = 0.09786 -0.01041 -0.00550 0.01660 C6 1 -0.051620 0.162752 0.188860 11.00000 0.03758 0.07517 = 0.12272 0.00406 -0.02928 0.00499 AFIX 43 H6 2 -0.132507 0.131305 0.171953 11.00000 -1.20000 AFIX 0 C7 1 -0.130102 0.168923 0.230596 11.00000 0.03454 0.07879 = 0.09737 -0.00619 -0.00784 -0.00934 C8 1 -0.321329 0.135276 0.252442 11.00000 0.02035 0.05400 = 0.17517 -0.00076 -0.03307 0.00611 C9 1 -0.307768 0.158679 0.293454 11.00000 0.04247 0.05635 = 0.19750 0.00116 -0.05004 -0.01388 C10 1 -0.113010 0.206059 0.299778 11.00000 0.03232 0.04627 = 0.12200 -0.01589 -0.00523 -0.00109 C11 1 -0.429870 0.155529 0.337299 11.00000 0.02775 0.12497 = 0.11352 0.04095 0.00657 0.00474 C12 1 -0.290646 0.199709 0.367923 11.00000 0.03173 0.08186 = 0.12725 -0.00174 0.01667 0.01940 AFIX 23 H12A 2 -0.219012 0.173633 0.391188 11.00000 -1.20000 H12B 2 -0.395132 0.233669 0.380433 11.00000 -1.20000 AFIX 0 C13 1 -0.091935 0.231941 0.339247 11.00000 0.02864 0.07624 = 0.11619 -0.00513 0.02494 0.00968 C14 1 0.066794 0.282674 0.353451 11.00000 0.02188 0.06406 = 0.10299 0.01712 0.02111 0.00466 C15 1 0.085379 0.314464 0.395817 11.00000 0.02390 0.17435 = 0.08196 0.02128 0.02958 -0.01009 AFIX 14 H15 2 -0.046350 0.338473 0.398782 11.00000 -1.20000 AFIX 0 C16 1 0.293087 0.365016 0.387322 11.00000 0.04012 0.09323 = 0.11072 0.02864 0.00352 -0.02429 AFIX 14 H16 2 0.432003 0.350889 0.406504 11.00000 -1.20000 AFIX 0 C17 1 0.366942 0.350447 0.343091 11.00000 0.03795 0.09097 = 0.05969 0.00448 0.03216 0.01839 C18 1 0.548746 0.385749 0.319971 11.00000 0.02747 0.10104 = 0.06418 -0.01242 0.00403 0.00800 AFIX 43 H18 2 0.622213 0.419316 0.336237 11.00000 -1.20000 AFIX 0 C19 1 0.635697 0.380835 0.279992 11.00000 0.02457 0.07279 = 0.11581 0.00703 -0.00372 0.01255 C20 1 0.817970 0.421161 0.257841 11.00000 0.03477 0.06096 = 0.09731 0.00985 0.00806 0.00121 C21 1 0.825973 0.403151 0.216957 11.00000 0.03891 0.08518 = 0.10189 0.01036 0.00285 -0.02325 C22 1 0.656804 0.350575 0.207768 11.00000 0.03404 0.07417 = 0.12783 -0.02767 -0.00375 -0.00101 C23 1 0.602800 0.318968 0.169476 11.00000 0.05423 0.13018 = 0.15422 -0.01005 0.02063 -0.03641 AFIX 43 H23 2 0.687295 0.335122 0.145539 11.00000 -1.20000 AFIX 0 C24 1 0.548675 0.247834 0.078516 11.00000 0.06261 0.16035 = 0.15963 -0.04409 0.00225 -0.01903 AFIX 137 H24A 2 0.559801 0.206408 0.062846 11.00000 -1.50000 H24B 2 0.708709 0.263918 0.084938 11.00000 -1.50000 H24C 2 0.464504 0.280294 0.061166 11.00000 -1.50000 AFIX 0 C25 1 0.129222 0.140513 0.091572 11.00000 0.04821 0.12489 = 0.14204 -0.03335 -0.00605 0.00600 AFIX 23 H25A 2 -0.041161 0.132836 0.097567 11.00000 -1.20000 H25B 2 0.141789 0.159727 0.062737 11.00000 -1.20000 AFIX 0 C26 1 0.259459 0.075371 0.092356 11.00000 0.17271 0.06500 = 0.24219 -0.05822 -0.00553 0.00954 AFIX 137 H26A 2 0.378511 0.075869 0.115089 11.00000 -1.50000 H26B 2 0.338235 0.068296 0.064944 11.00000 -1.50000 H26C 2 0.145730 0.039884 0.097540 11.00000 -1.50000 AFIX 0 C27 1 -0.498786 0.087444 0.233036 11.00000 0.03486 0.04524 = 0.21021 -0.01404 -0.05828 0.00385 AFIX 137 H27A 2 -0.653228 0.109081 0.229949 11.00000 -1.50000 H27B 2 -0.515349 0.049161 0.251641 11.00000 -1.50000 H27C 2 -0.441900 0.073331 0.205037 11.00000 -1.50000 AFIX 0 C28 1 0.103902 0.273836 0.435365 11.00000 0.02738 0.14846 = 0.11720 0.02567 0.00432 -0.00390 AFIX 23 H28A 2 0.242407 0.244332 0.432149 11.00000 -1.20000 H28B 2 -0.039257 0.245750 0.436993 11.00000 -1.20000 AFIX 0 C29 1 0.130045 0.311012 0.479544 11.00000 0.02439 0.14195 = 0.14903 0.03282 0.02659 0.02008 AFIX 23 H29A 2 0.169560 0.278645 0.501928 11.00000 -1.20000 H29B 2 0.263759 0.342401 0.477571 11.00000 -1.20000 AFIX 0 C30 1 -0.099765 0.349129 0.493011 11.00000 0.14167 0.11021 = 0.07199 0.00976 0.01474 0.01752 C31 1 -0.257900 0.417639 0.549651 11.00000 0.05735 0.17793 = 0.19431 -0.08691 -0.02334 0.03505 AFIX 137 H31A 2 -0.390747 0.388348 0.556324 11.00000 -1.50000 H31B 2 -0.310878 0.451370 0.529581 11.00000 -1.50000 H31C 2 -0.201495 0.438586 0.575821 11.00000 -1.50000 AFIX 0 C32 1 0.237640 0.435100 0.398952 11.00000 0.07048 0.08760 = 0.13531 -0.00132 0.01542 -0.02789 AFIX 137 H32A 2 0.143375 0.455269 0.376250 11.00000 -1.50000 H32B 2 0.386143 0.459530 0.402570 11.00000 -1.50000 H32C 2 0.147369 0.436046 0.425593 11.00000 -1.50000 AFIX 0 C33 1 0.971579 0.471067 0.279848 11.00000 0.03788 0.12574 = 0.12389 -0.02014 0.02562 -0.03551 AFIX 137 H33A 2 1.044878 0.499814 0.258600 11.00000 -1.50000 H33B 2 1.095962 0.448572 0.296048 11.00000 -1.50000 H33C 2 0.873972 0.497326 0.299235 11.00000 -1.50000 AFIX 0 C34 1 0.977949 0.427358 0.180820 11.00000 0.12246 0.14276 = 0.16224 0.04347 -0.04536 -0.06498 AFIX 14 H34 2 1.089600 0.388560 0.173897 11.00000 -1.20000 AFIX 0 C35 1 0.933080 0.456271 0.142134 11.00000 0.08481 0.11988 = 0.19256 0.01512 -0.01706 0.02794 AFIX 14 H35 2 0.777298 0.482029 0.140406 11.00000 -1.20000 AFIX 66 C36 1 1.040481 0.434135 0.097561 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 C37 1 1.246218 0.466910 0.082488 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 AFIX 43 H37 2 1.330012 0.496057 0.100630 11.00000 -1.20000 AFIX 65 C38 1 1.326715 0.456122 0.040299 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 AFIX 43 H38 2 1.464367 0.478051 0.030214 11.00000 -1.20000 AFIX 65 C39 1 1.201476 0.412559 0.013183 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 AFIX 43 H39 2 1.255335 0.405342 -0.015045 11.00000 -1.20000 AFIX 65 C40 1 0.995739 0.379784 0.028255 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 AFIX 43 H40 2 0.911947 0.350638 0.010113 11.00000 -1.20000 AFIX 65 C41 1 0.915240 0.390572 0.070444 11.00000 0.23169 0.26144 = 0.18385 -0.04450 0.03847 -0.05479 AFIX 43 H41 2 0.777588 0.368643 0.080528 11.00000 -1.20000 AFIX 0 C42 1 1.119574 0.482421 0.177205 11.00000 0.38897 0.20642 = 0.10284 -0.06142 0.03140 -0.08579 AFIX 23 H42A 2 1.291303 0.476263 0.171726 11.00000 -1.20000 H42B 2 1.076973 0.521770 0.194007 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)2(1)2(1) REM R1 = 0.1405 for 1204 Fo > 4sig(Fo) and 0.3021 for all 4491 data REM 401 parameters refined using 84 restraints END WGHT 0.1884 0.0000 REM Instructions for potential hydrogen bonds HTAB N2 N1 HTAB N2 N4 HTAB N3 N1 HTAB C15 O2 HTAB C16 O2_$1 HTAB C29 O2_$1 REM Highest difference peak 0.356, deepest hole -0.449, 1-sigma level 0.082 Q1 1 1.1181 0.3656 0.0690 11.00000 0.05 0.36 Q2 1 1.1776 0.3740 0.0310 11.00000 0.05 0.35 Q3 1 -0.3138 0.3484 0.5534 11.00000 0.05 0.31 Q4 1 1.1494 0.4270 0.1007 11.00000 0.05 0.30 Q5 1 1.1205 0.4003 0.1460 11.00000 0.05 0.28 Q6 1 -0.4116 0.1283 0.2481 11.00000 0.05 0.27 Q7 1 -0.3767 0.2050 0.3932 11.00000 0.05 0.26 Q8 1 0.6413 0.4726 0.2262 11.00000 0.05 0.23 Q9 1 0.8000 0.2611 0.0258 11.00000 0.05 0.22 Q10 1 0.1633 0.2613 0.2297 11.00000 0.05 0.22 Q11 1 0.1832 0.3141 0.3233 11.00000 0.05 0.22 Q12 1 0.3385 0.3425 0.2963 11.00000 0.05 0.22 Q13 1 0.3501 0.3861 0.3840 11.00000 0.05 0.21 Q14 1 -0.2099 0.0923 0.2887 11.00000 0.05 0.21 Q15 1 -0.3146 0.1213 0.2833 11.00000 0.05 0.21 Q16 1 -0.5161 0.1286 0.3321 11.00000 0.05 0.21 Q17 1 -0.4589 0.1017 0.3241 11.00000 0.05 0.21 Q18 1 -0.2859 0.1384 0.2949 11.00000 0.05 0.21 Q19 1 -0.6801 0.1638 0.3105 11.00000 0.05 0.20 Q20 1 -0.3317 0.3542 0.4675 11.00000 0.05 0.20 ; _shelx_res_checksum 95943 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 O1 O -0.602(3) 0.1184(9) 0.3478(6) 0.124(6) Uani 1 1 d . . . . . O2 O -0.273(2) 0.3512(11) 0.4711(6) 0.130(7) Uani 1 1 d D . . . . O3 O -0.059(3) 0.3785(9) 0.5300(7) 0.120(6) Uani 1 1 d D . . . . N1 N 0.277(3) 0.2442(10) 0.1907(6) 0.090(5) Uani 1 1 d D . . . . N2 N 0.541(3) 0.3432(9) 0.2468(6) 0.078(5) Uani 1 1 d D . . . . H2 H 0.419019 0.317085 0.250215 0.093 Uiso 1 1 calc R U . . . N3 N -0.014(3) 0.2099(9) 0.2599(6) 0.081(5) Uani 1 1 d D . . . . H3 H 0.107616 0.234967 0.253530 0.097 Uiso 1 1 calc R U . . . N4 N 0.228(3) 0.3042(9) 0.3214(5) 0.075(5) Uani 1 1 d D . . . . C2 C 0.438(4) 0.2650(12) 0.1599(8) 0.081(6) Uani 1 1 d D . . . . C3 C 0.415(4) 0.2369(12) 0.1193(8) 0.084(6) Uani 1 1 d D . . . . C4 C 0.230(5) 0.1904(11) 0.1247(8) 0.090(7) Uani 1 1 d D . . . . C5 C 0.138(4) 0.1982(11) 0.1680(8) 0.075(6) Uani 1 1 d D . . . . C6 C -0.052(4) 0.1628(11) 0.1889(8) 0.078(6) Uani 1 1 d D . . . . H6 H -0.132507 0.131305 0.171953 0.094 Uiso 1 1 calc R U . . . C7 C -0.130(3) 0.1689(10) 0.2306(7) 0.070(6) Uani 1 1 d D . . . . C8 C -0.321(3) 0.1353(10) 0.2524(9) 0.083(7) Uani 1 1 d D . . . . C9 C -0.308(4) 0.1587(12) 0.2935(11) 0.099(9) Uani 1 1 d . . . . . C10 C -0.113(3) 0.2061(9) 0.2998(7) 0.067(6) Uani 1 1 d D . . . . C11 C -0.430(4) 0.1555(14) 0.3373(8) 0.089(7) Uani 1 1 d . . . . . C12 C -0.291(3) 0.1997(11) 0.3679(7) 0.080(6) Uani 1 1 d . . . . . H12A H -0.219012 0.173633 0.391188 0.096 Uiso 1 1 calc R U . . . H12B H -0.395132 0.233669 0.380433 0.096 Uiso 1 1 calc R U . . . C13 C -0.092(3) 0.2319(11) 0.3392(8) 0.074(6) Uani 1 1 d . . . . . C14 C 0.067(3) 0.2827(10) 0.3535(6) 0.063(5) Uani 1 1 d D . . . . C15 C 0.085(3) 0.3145(12) 0.3958(6) 0.093(9) Uani 1 1 d D . . . . H15 H -0.05(4) 0.338(7) 0.3988(11) 0.112 Uiso 1 1 calc R U . . . C16 C 0.293(3) 0.3650(11) 0.3873(7) 0.081(6) Uani 1 1 d D . . . . H16 H 0.432(7) 0.3509(13) 0.4065(11) 0.098 Uiso 1 1 calc DR U . . . C17 C 0.367(3) 0.3504(10) 0.3431(6) 0.063(5) Uani 1 1 d D . . . . C18 C 0.549(3) 0.3857(10) 0.3200(6) 0.064(5) Uani 1 1 d D . . . . H18 H 0.622213 0.419316 0.336237 0.077 Uiso 1 1 calc R U . . . C19 C 0.636(3) 0.3808(10) 0.2800(7) 0.071(6) Uani 1 1 d D . . . . C20 C 0.818(3) 0.4212(9) 0.2578(7) 0.064(5) Uani 1 1 d D . . . . C21 C 0.826(3) 0.4032(11) 0.2170(8) 0.075(6) Uani 1 1 d D . . . . C22 C 0.657(4) 0.3506(11) 0.2078(7) 0.079(6) Uani 1 1 d D . . . . C23 C 0.603(4) 0.3190(14) 0.1695(9) 0.113(9) Uani 1 1 d D . . . . H23 H 0.687295 0.335122 0.145539 0.135 Uiso 1 1 calc R U . . . C24 C 0.549(5) 0.2478(15) 0.0785(8) 0.128(10) Uani 1 1 d D . . . . H24A H 0.559801 0.206408 0.062846 0.191 Uiso 1 1 calc R U . . . H24B H 0.708709 0.263918 0.084938 0.191 Uiso 1 1 calc R U . . . H24C H 0.464504 0.280294 0.061166 0.191 Uiso 1 1 calc R U . . . C25 C 0.129(4) 0.1405(12) 0.0916(8) 0.105(8) Uani 1 1 d D . . . . H25A H -0.041161 0.132836 0.097567 0.126 Uiso 1 1 calc R U . . . H25B H 0.141789 0.159727 0.062737 0.126 Uiso 1 1 calc R U . . . C26 C 0.259(6) 0.0754(13) 0.0924(10) 0.160(12) Uani 1 1 d D . . . . H26A H 0.378511 0.075869 0.115089 0.240 Uiso 1 1 calc R U . . . H26B H 0.338235 0.068296 0.064944 0.240 Uiso 1 1 calc R U . . . H26C H 0.145730 0.039884 0.097540 0.240 Uiso 1 1 calc R U . . . C27 C -0.499(3) 0.0874(9) 0.2330(8) 0.097(8) Uani 1 1 d D . . . . H27A H -0.653228 0.109081 0.229949 0.145 Uiso 1 1 calc R U . . . H27B H -0.515349 0.049161 0.251641 0.145 Uiso 1 1 calc R U . . . H27C H -0.441900 0.073331 0.205037 0.145 Uiso 1 1 calc R U . . . C28 C 0.104(4) 0.2738(13) 0.4354(7) 0.098(8) Uani 1 1 d D . . . . H28A H 0.242407 0.244332 0.432149 0.117 Uiso 1 1 calc R U . . . H28B H -0.039257 0.245750 0.436993 0.117 Uiso 1 1 calc R U . . . C29 C 0.130(3) 0.3110(13) 0.4795(8) 0.105(8) Uani 1 1 d D . . . . H29A H 0.169560 0.278645 0.501928 0.126 Uiso 1 1 calc R U . . . H29B H 0.263759 0.342401 0.477571 0.126 Uiso 1 1 calc R U . . . C30 C -0.100(5) 0.3491(13) 0.4930(7) 0.108(9) Uani 1 1 d D . . . . C31 C -0.258(5) 0.4176(16) 0.5497(9) 0.143(13) Uani 1 1 d . . . . . H31A H -0.390747 0.388348 0.556324 0.215 Uiso 1 1 calc R U . . . H31B H -0.310878 0.451370 0.529581 0.215 Uiso 1 1 calc R U . . . H31C H -0.201495 0.438586 0.575821 0.215 Uiso 1 1 calc R U . . . C32 C 0.238(4) 0.4351(12) 0.3990(7) 0.098(7) Uani 1 1 d D . . . . H32A H 0.143375 0.455269 0.376250 0.147 Uiso 1 1 calc R U . . . H32B H 0.386143 0.459530 0.402570 0.147 Uiso 1 1 calc R U . . . H32C H 0.147369 0.436046 0.425593 0.147 Uiso 1 1 calc R U . . . C33 C 0.972(3) 0.4711(12) 0.2798(7) 0.096(7) Uani 1 1 d D . . . . H33A H 1.044878 0.499814 0.258600 0.144 Uiso 1 1 calc R U . . . H33B H 1.095962 0.448572 0.296048 0.144 Uiso 1 1 calc R U . . . H33C H 0.873972 0.497326 0.299235 0.144 Uiso 1 1 calc R U . . . C34 C 0.978(6) 0.4274(19) 0.1808(10) 0.142(12) Uani 1 1 d D U . . . H34 H 1.090(7) 0.389(2) 0.1739(10) 0.171 Uiso 1 1 calc DR U . . . C35 C 0.933(5) 0.4563(15) 0.1421(9) 0.132(10) Uani 1 1 d D U . . . H35 H 0.777(8) 0.4820(19) 0.1404(9) 0.159 Uiso 1 1 calc DR U . . . C36 C 1.040(6) 0.4341(18) 0.0976(7) 0.226(8) Uani 1 1 d DG U . . . C37 C 1.246(6) 0.4669(16) 0.0825(9) 0.226(8) Uani 1 1 d G U . . . H37 H 1.330012 0.496057 0.100630 0.271 Uiso 1 1 calc R U . . . C38 C 1.327(5) 0.4561(16) 0.0403(9) 0.226(8) Uani 1 1 d G U . . . H38 H 1.464367 0.478051 0.030214 0.271 Uiso 1 1 calc R U . . . C39 C 1.201(6) 0.4126(17) 0.0132(6) 0.226(8) Uani 1 1 d G U . . . H39 H 1.255335 0.405342 -0.015045 0.271 Uiso 1 1 calc R U . . . C40 C 0.996(6) 0.3798(16) 0.0283(9) 0.226(8) Uani 1 1 d G U . . . H40 H 0.911947 0.350638 0.010113 0.271 Uiso 1 1 calc R U . . . C41 C 0.915(5) 0.3906(16) 0.0704(9) 0.226(8) Uani 1 1 d G U . . . H41 H 0.777588 0.368643 0.080528 0.271 Uiso 1 1 calc R U . . . C42 C 1.120(8) 0.482(2) 0.1772(9) 0.23(3) Uani 1 1 d D . . . . H42A H 1.291303 0.476263 0.171726 0.279 Uiso 1 1 calc R U . . . H42B H 1.076973 0.521770 0.194007 0.279 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 0.058(11) 0.118(15) 0.197(16) 0.037(11) 0.009(10) -0.026(11) O2 0.015(9) 0.22(2) 0.149(15) -0.011(12) -0.031(8) 0.022(10) O3 0.087(12) 0.125(15) 0.149(16) -0.017(12) -0.001(11) -0.009(12) N1 0.037(12) 0.095(15) 0.137(16) -0.013(12) 0.004(11) 0.029(11) N2 0.012(9) 0.105(14) 0.117(15) -0.024(10) 0.012(9) -0.006(9) N3 0.034(10) 0.097(14) 0.112(14) -0.026(10) 0.016(10) -0.004(9) N4 0.018(9) 0.090(13) 0.115(13) -0.024(10) 0.015(9) 0.020(9) C2 0.034(14) 0.088(18) 0.12(2) -0.001(14) -0.021(13) 0.011(13) C3 0.046(14) 0.075(17) 0.13(2) -0.011(13) -0.002(14) -0.016(13) C4 0.073(18) 0.061(16) 0.14(2) 0.000(13) -0.037(15) 0.034(15) C5 0.053(15) 0.074(16) 0.098(17) -0.010(12) -0.006(13) 0.017(14) C6 0.038(13) 0.075(15) 0.12(2) 0.004(13) -0.029(12) 0.005(12) C7 0.035(13) 0.079(16) 0.097(17) -0.006(12) -0.008(11) -0.009(12) C8 0.020(12) 0.054(14) 0.18(2) -0.001(14) -0.033(13) 0.006(10) C9 0.042(15) 0.056(15) 0.20(3) 0.001(15) -0.050(17) -0.014(12) C10 0.032(13) 0.046(12) 0.12(2) -0.016(11) -0.005(12) -0.001(10) C11 0.028(13) 0.12(2) 0.114(19) 0.041(15) 0.007(13) 0.005(15) C12 0.032(12) 0.082(16) 0.127(17) -0.002(12) 0.017(12) 0.019(12) C13 0.029(12) 0.076(16) 0.116(18) -0.005(12) 0.025(11) 0.010(12) C14 0.022(11) 0.064(13) 0.103(17) 0.017(10) 0.021(10) 0.005(11) C15 0.024(11) 0.17(3) 0.082(16) 0.021(16) 0.030(10) -0.010(13) C16 0.040(13) 0.09(2) 0.111(17) 0.029(12) 0.004(11) -0.024(13) C17 0.038(12) 0.091(15) 0.060(12) 0.004(10) 0.032(10) 0.018(12) C18 0.027(11) 0.101(16) 0.064(13) -0.012(10) 0.004(9) 0.008(11) C19 0.025(11) 0.073(14) 0.116(19) 0.007(12) -0.004(12) 0.013(11) C20 0.035(12) 0.061(14) 0.097(16) 0.010(10) 0.008(11) 0.001(11) C21 0.039(13) 0.085(16) 0.102(17) 0.010(12) 0.003(11) -0.023(12) C22 0.034(12) 0.074(15) 0.128(19) -0.028(13) -0.004(13) -0.001(12) C23 0.054(16) 0.13(2) 0.15(2) -0.010(18) 0.021(14) -0.036(17) C24 0.063(17) 0.16(3) 0.16(3) -0.044(19) 0.002(17) -0.019(17) C25 0.048(14) 0.12(2) 0.14(2) -0.033(16) -0.006(12) 0.006(15) C26 0.17(3) 0.065(18) 0.24(3) -0.058(18) -0.01(3) 0.01(2) C27 0.035(13) 0.045(13) 0.21(2) -0.014(12) -0.058(14) 0.004(10) C28 0.027(12) 0.15(2) 0.12(2) 0.026(17) 0.004(11) -0.004(13) C29 0.024(12) 0.14(2) 0.15(2) 0.033(17) 0.027(13) 0.020(14) C30 0.14(3) 0.11(2) 0.072(17) 0.010(13) 0.015(18) 0.02(2) C31 0.057(17) 0.18(3) 0.19(3) -0.09(2) -0.023(17) 0.035(19) C32 0.070(16) 0.088(19) 0.135(18) -0.001(13) 0.015(14) -0.028(15) C33 0.038(13) 0.13(2) 0.124(18) -0.020(14) 0.026(12) -0.036(14) C34 0.12(2) 0.14(3) 0.16(3) 0.04(2) -0.05(2) -0.06(2) C35 0.085(19) 0.12(2) 0.19(3) 0.015(19) -0.017(18) 0.028(18) C36 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C37 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C38 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C39 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C40 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C41 0.232(17) 0.261(17) 0.184(12) -0.044(12) 0.038(12) -0.055(14) C42 0.39(8) 0.21(4) 0.10(2) -0.06(2) 0.03(3) -0.09(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' O O 0.0492 0.0322 '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 C30 O3 C31 117.8(18) . . ? C2 N1 C5 102.1(19) . . ? C22 N2 C19 114.8(17) . . ? C22 N2 H2 122.6 . . ? C19 N2 H2 122.6 . . ? C10 N3 C7 112.1(17) . . ? C10 N3 H3 124.0 . . ? C7 N3 H3 124.0 . . ? C17 N4 C14 102.6(15) . . ? N1 C2 C3 117(2) . . ? N1 C2 C23 120(2) . . ? C3 C2 C23 123(2) . . ? C2 C3 C4 103(2) . . ? C2 C3 C24 132(2) . . ? C4 C3 C24 125(2) . . ? C3 C4 C5 107.4(19) . . ? C3 C4 C25 128(2) . . ? C5 C4 C25 124(2) . . ? N1 C5 C6 121(2) . . ? N1 C5 C4 110(2) . . ? C6 C5 C4 129(2) . . ? C7 C6 C5 128(2) . . ? C7 C6 H6 115.9 . . ? C5 C6 H6 115.9 . . ? C6 C7 N3 122(2) . . ? C6 C7 C8 130(2) . . ? N3 C7 C8 108.4(19) . . ? C9 C8 C7 103.8(18) . . ? C9 C8 C27 129(2) . . ? C7 C8 C27 127(2) . . ? C8 C9 C10 113(3) . . ? C8 C9 C11 143(2) . . ? C10 C9 C11 104(2) . . ? C13 C10 N3 141.1(19) . . ? C13 C10 C9 116(2) . . ? N3 C10 C9 102(2) . . ? O1 C11 C12 125(2) . . ? O1 C11 C9 127(3) . . ? C12 C11 C9 108(2) . . ? C11 C12 C13 104.4(18) . . ? C11 C12 H12A 110.9 . . ? C13 C12 H12A 110.9 . . ? C11 C12 H12B 110.9 . . ? C13 C12 H12B 110.9 . . ? H12A C12 H12B 108.9 . . ? C10 C13 C14 128.3(18) . . ? C10 C13 C12 107(2) . . ? C14 C13 C12 124.2(19) . . ? N4 C14 C13 113.5(18) . . ? N4 C14 C15 117.0(17) . . ? C13 C14 C15 129.5(15) . . ? C14 C15 C28 121(2) . . ? C14 C15 C16 100.7(15) . . ? C28 C15 C16 116.7(16) . . ? C14 C15 H15 105.9 . . ? C28 C15 H15 105.9 . . ? C16 C15 H15 105.9 . . ? C17 C16 C32 118.4(16) . . ? C17 C16 C15 103.6(17) . . ? C32 C16 C15 115.1(18) . . ? C17 C16 H16 106.3 . . ? C32 C16 H16 106.3 . . ? C15 C16 H16 106.3 . . ? N4 C17 C18 118.9(16) . . ? N4 C17 C16 115.9(15) . . ? C18 C17 C16 124.8(18) . . ? C19 C18 C17 133.3(18) . . ? C19 C18 H18 113.3 . . ? C17 C18 H18 113.3 . . ? C18 C19 N2 126.6(19) . . ? C18 C19 C20 130.1(19) . . ? N2 C19 C20 102.4(18) . . ? C21 C20 C19 108.7(18) . . ? C21 C20 C33 127.5(18) . . ? C19 C20 C33 124(2) . . ? C20 C21 C22 111.7(18) . . ? C20 C21 C34 131(2) . . ? C22 C21 C34 117(2) . . ? N2 C22 C23 127(2) . . ? N2 C22 C21 102.0(18) . . ? C23 C22 C21 130(2) . . ? C22 C23 C2 131(2) . . ? C22 C23 H23 114.4 . . ? C2 C23 H23 114.4 . . ? C3 C24 H24A 109.5 . . ? C3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C4 112.6(18) . . ? C26 C25 H25A 109.1 . . ? C4 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C4 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C8 C27 H27A 109.5 . . ? C8 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C8 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C15 C28 C29 118(2) . . ? C15 C28 H28A 107.8 . . ? C29 C28 H28A 107.8 . . ? C15 C28 H28B 107.8 . . ? C29 C28 H28B 107.8 . . ? H28A C28 H28B 107.2 . . ? C30 C29 C28 113.3(19) . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29B 108.9 . . ? C28 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? O2 C30 O3 129(2) . . ? O2 C30 C29 122(2) . . ? O3 C30 C29 108(2) . . ? O3 C31 H31A 109.5 . . ? O3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C16 C32 H32A 109.5 . . ? C16 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C16 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C20 C33 H33A 109.5 . . ? C20 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C20 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C42 71.6(18) . . ? C35 C34 C21 135(3) . . ? C42 C34 C21 131(3) . . ? C35 C34 H34 104.7 . . ? C42 C34 H34 104.7 . . ? C21 C34 H34 104.7 . . ? C34 C35 C36 126(3) . . ? C34 C35 C42 54.4(15) . . ? C36 C35 C42 117(3) . . ? C34 C35 H35 115.1 . . ? C36 C35 H35 115.1 . . ? C42 C35 H35 115.1 . . ? C37 C36 C41 120.0 . . ? C37 C36 C35 118(2) . . ? C41 C36 C35 121(2) . . ? C36 C37 C38 120.0 . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C39 C38 C37 120.0 . . ? C39 C38 H38 120.0 . . ? C37 C38 H38 120.0 . . ? C38 C39 C40 120.0 . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C41 C40 C39 120.0 . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C40 C41 C36 120.0 . . ? C40 C41 H41 120.0 . . ? C36 C41 H41 120.0 . . ? C34 C42 C35 54.0(15) . . ? C34 C42 H42A 118.3 . . ? C35 C42 H42A 118.3 . . ? C34 C42 H42B 118.3 . . ? C35 C42 H42B 118.3 . . ? H42A C42 H42B 115.6 . . ? 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 C11 1.25(3) . ? O2 C30 1.17(2) . ? O3 C30 1.30(2) . ? O3 C31 1.48(3) . ? N1 C2 1.363(19) . ? N1 C5 1.386(19) . ? N2 C22 1.368(19) . ? N2 C19 1.372(18) . ? N2 H2 0.8600 . ? N3 C10 1.346(19) . ? N3 C7 1.377(18) . ? N3 H3 0.8600 . ? N4 C17 1.372(18) . ? N4 C14 1.399(17) . ? C2 C3 1.38(2) . ? C2 C23 1.44(3) . ? C3 C4 1.39(3) . ? C3 C24 1.47(3) . ? C4 C5 1.43(3) . ? C4 C25 1.53(3) . ? C5 C6 1.42(2) . ? C6 C7 1.36(2) . ? C6 H6 0.9300 . ? C7 C8 1.42(3) . ? C8 C9 1.35(3) . ? C8 C27 1.49(2) . ? C9 C10 1.44(3) . ? C9 C11 1.51(4) . ? C10 C13 1.33(3) . ? C11 C12 1.50(3) . ? C12 C13 1.55(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.41(3) . ? C14 C15 1.45(2) . ? C15 C28 1.47(2) . ? C15 C16 1.55(2) . ? C15 H15 0.9(2) . ? C16 C17 1.45(3) . ? C16 C32 1.48(2) . ? C16 H16 1.01(4) . ? C17 C18 1.42(2) . ? C18 C19 1.33(2) . ? C18 H18 0.9300 . ? C19 C20 1.46(3) . ? C20 C21 1.31(2) . ? C20 C33 1.47(2) . ? C21 C22 1.43(3) . ? C21 C34 1.47(3) . ? C22 C23 1.37(3) . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.49(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.56(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.54(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.35(3) . ? C34 C42 1.35(3) . ? C34 H34 1.01(4) . ? C35 C36 1.56(3) . ? C35 C42 1.58(3) . ? C35 H35 1.00(4) . ? C36 C37 1.3900 . ? C36 C41 1.3900 . ? C37 C38 1.3900 . ? C37 H37 0.9300 . ? C38 C39 1.3900 . ? C38 H38 0.9300 . ? C39 C40 1.3900 . ? C39 H39 0.9300 . ? C40 C41 1.3900 . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.86 2.47 3.01(3) 121.1 . N2 H2 N4 0.86 2.44 2.98(2) 120.8 . N3 H3 N1 0.86 2.16 2.76(3) 126.3 . C15 H15 O2 0.88 2.57 3.14(3) 123.3 . C16 H16 O2 1.01 2.57 3.53(3) 159.1 1_655 C29 H29B O2 0.97 2.57 3.40(2) 143.7 1_655 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 C5 N1 C2 C3 0(2) . . . . ? C5 N1 C2 C23 173.9(19) . . . . ? N1 C2 C3 C4 -3(2) . . . . ? C23 C2 C3 C4 -176.8(19) . . . . ? N1 C2 C3 C24 178(2) . . . . ? C23 C2 C3 C24 5(4) . . . . ? C2 C3 C4 C5 5(2) . . . . ? C24 C3 C4 C5 -177(2) . . . . ? C2 C3 C4 C25 -177(2) . . . . ? C24 C3 C4 C25 2(3) . . . . ? C2 N1 C5 C6 178.4(17) . . . . ? C2 N1 C5 C4 3(2) . . . . ? C3 C4 C5 N1 -5(2) . . . . ? C25 C4 C5 N1 176.2(19) . . . . ? C3 C4 C5 C6 179.8(19) . . . . ? C25 C4 C5 C6 1(3) . . . . ? N1 C5 C6 C7 3(3) . . . . ? C4 C5 C6 C7 177(2) . . . . ? C5 C6 C7 N3 -5(3) . . . . ? C5 C6 C7 C8 178.8(18) . . . . ? C10 N3 C7 C6 -176.8(18) . . . . ? C10 N3 C7 C8 0(2) . . . . ? C6 C7 C8 C9 177(2) . . . . ? N3 C7 C8 C9 0(2) . . . . ? C6 C7 C8 C27 -5(3) . . . . ? N3 C7 C8 C27 178.2(18) . . . . ? C7 C8 C9 C10 -1(2) . . . . ? C27 C8 C9 C10 -178.4(18) . . . . ? C7 C8 C9 C11 177(3) . . . . ? C27 C8 C9 C11 -1(4) . . . . ? C7 N3 C10 C13 -178(2) . . . . ? C7 N3 C10 C9 0(2) . . . . ? C8 C9 C10 C13 178.9(18) . . . . ? C11 C9 C10 C13 1(2) . . . . ? C8 C9 C10 N3 1(2) . . . . ? C11 C9 C10 N3 -177.6(16) . . . . ? C8 C9 C11 O1 6(4) . . . . ? C10 C9 C11 O1 -176(2) . . . . ? C8 C9 C11 C12 -180(3) . . . . ? C10 C9 C11 C12 -3(2) . . . . ? O1 C11 C12 C13 177(2) . . . . ? C9 C11 C12 C13 3(2) . . . . ? N3 C10 C13 C14 3(4) . . . . ? C9 C10 C13 C14 -174.4(18) . . . . ? N3 C10 C13 C12 179(2) . . . . ? C9 C10 C13 C12 2(2) . . . . ? C11 C12 C13 C10 -3(2) . . . . ? C11 C12 C13 C14 173.1(19) . . . . ? C17 N4 C14 C13 -177.6(17) . . . . ? C17 N4 C14 C15 2(2) . . . . ? C10 C13 C14 N4 -4(3) . . . . ? C12 C13 C14 N4 -179.2(16) . . . . ? C10 C13 C14 C15 176(2) . . . . ? C12 C13 C14 C15 1(3) . . . . ? N4 C14 C15 C28 -128.9(17) . . . . ? C13 C14 C15 C28 51(3) . . . . ? N4 C14 C15 C16 1(2) . . . . ? C13 C14 C15 C16 -179.3(19) . . . . ? C14 C15 C16 C17 -4(2) . . . . ? C28 C15 C16 C17 129(2) . . . . ? C14 C15 C16 C32 127(2) . . . . ? C28 C15 C16 C32 -100(2) . . . . ? C14 N4 C17 C18 -177.5(15) . . . . ? C14 N4 C17 C16 -5(2) . . . . ? C32 C16 C17 N4 -123(2) . . . . ? C15 C16 C17 N4 6(2) . . . . ? C32 C16 C17 C18 49(3) . . . . ? C15 C16 C17 C18 177.8(17) . . . . ? N4 C17 C18 C19 -6(3) . . . . ? C16 C17 C18 C19 -178(2) . . . . ? C17 C18 C19 N2 10(3) . . . . ? C17 C18 C19 C20 177.2(19) . . . . ? C22 N2 C19 C18 175.7(19) . . . . ? C22 N2 C19 C20 6(2) . . . . ? C18 C19 C20 C21 -173(2) . . . . ? N2 C19 C20 C21 -3(2) . . . . ? C18 C19 C20 C33 10(3) . . . . ? N2 C19 C20 C33 179.5(19) . . . . ? C19 C20 C21 C22 0(2) . . . . ? C33 C20 C21 C22 177(2) . . . . ? C19 C20 C21 C34 -180(3) . . . . ? C33 C20 C21 C34 -2(4) . . . . ? C19 N2 C22 C23 179(2) . . . . ? C19 N2 C22 C21 -6(2) . . . . ? C20 C21 C22 N2 4(2) . . . . ? C34 C21 C22 N2 -177(2) . . . . ? C20 C21 C22 C23 178(2) . . . . ? C34 C21 C22 C23 -3(4) . . . . ? N2 C22 C23 C2 -9(4) . . . . ? C21 C22 C23 C2 178(2) . . . . ? N1 C2 C23 C22 10(4) . . . . ? C3 C2 C23 C22 -177(3) . . . . ? C3 C4 C25 C26 89(3) . . . . ? C5 C4 C25 C26 -93(3) . . . . ? C14 C15 C28 C29 178.4(16) . . . . ? C16 C15 C28 C29 56(3) . . . . ? C15 C28 C29 C30 69(2) . . . . ? C31 O3 C30 O2 4(4) . . . . ? C31 O3 C30 C29 -179(2) . . . . ? C28 C29 C30 O2 -2(4) . . . . ? C28 C29 C30 O3 -179.6(19) . . . . ? C20 C21 C34 C35 -120(4) . . . . ? C22 C21 C34 C35 61(5) . . . . ? C20 C21 C34 C42 -14(6) . . . . ? C22 C21 C34 C42 167(4) . . . . ? C42 C34 C35 C36 99(4) . . . . ? C21 C34 C35 C36 -131(4) . . . . ? C21 C34 C35 C42 130(5) . . . . ? C34 C35 C36 C37 -96(3) . . . . ? C42 C35 C36 C37 -32(4) . . . . ? C34 C35 C36 C41 94(3) . . . . ? C42 C35 C36 C41 158(3) . . . . ? C41 C36 C37 C38 0.0 . . . . ? C35 C36 C37 C38 -170(3) . . . . ? C36 C37 C38 C39 0.0 . . . . ? C37 C38 C39 C40 0.0 . . . . ? C38 C39 C40 C41 0.0 . . . . ? C39 C40 C41 C36 0.0 . . . . ? C37 C36 C41 C40 0.0 . . . . ? C35 C36 C41 C40 170(3) . . . . ? C21 C34 C42 C35 -134(4) . . . . ? C36 C35 C42 C34 -117(4) . . . . ?