#------------------------------------------------------------------------------ #$Date: 2020-04-21 02:02:28 +0300 (Tue, 21 Apr 2020) $ #$Revision: 250959 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557829.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_1557829 loop_ _publ_author_name 'Sessler, Jonathan L.' 'Guo, Chenxing' 'Wang, Hu' 'Lynch, Vincent' 'Ji, Xiaofan' 'Page, Zachariah A.' _publ_section_title ; Molecular recognition of pyrazine N,N’-dioxide using aryl extended calix[4]pyrroles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01496F _journal_year 2020 _chemical_formula_moiety '2 C40 H38 N6, C4 H4 N2 O2, 2 C H4 O' _chemical_formula_sum 'C86 H88 N14 O4' _chemical_formula_weight 1381.70 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-02-20 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.327(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 16.7110(7) _cell_length_b 12.6971(5) _cell_length_c 18.2586(7) _cell_measurement_reflns_used 12900 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 1.78 _cell_volume 3822.9(3) _computing_cell_refinement 'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction' _computing_data_collection 'CrystalClear 1.40 (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material 'XP SHELXTL/PC, Siemens Analytical' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2015)' _computing_structure_solution ; Sheldrick. G. M. (2015) SHELXT. Acta Cryst. A71, 3-8. ; _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nonius Kappa CCD with a Bruker Apex II detector' _diffrn_measurement_method \w-scans _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 45512 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.349 _diffrn_reflns_theta_min 1.804 _diffrn_source 'fine focus sealed tube' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.200 _exptl_crystal_description prism _exptl_crystal_F_000 1468 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.094 _refine_diff_density_max 0.944 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.089 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 508 _refine_ls_number_reflns 7000 _refine_ls_number_restraints 21 _refine_ls_restrained_S_all 1.169 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_gt 0.0982 _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^)+(0.1016P)^2^+4.5981P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2234 _refine_ls_wR_factor_ref 0.2381 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5433 _reflns_number_total 7000 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01496f3.cif _cod_data_source_block shelx_CCDC1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557829 _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_estimated_absorpt_t_min 0.984 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL c4pcn-pyrazine_a.res in P2(1)/n shelx.res created by SHELXL-2016/6 at 13:03:07 on 23-Apr-2019 CELL 0.71073 16.7110 12.6971 18.2586 90.000 99.327 90.000 ZERR 2.00 0.0007 0.0005 0.0007 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 172 176 28 8 MERG 2 SHEL 20 0.83 FMAP 2 PLAN 20 ACTA BOND $H eadp c20 c20a simu .01 .02 c25 c26 c25a c26a CONF LIST 4 size .21 .13 .094 HTAB N1 O1 HTAB N2 N7 HTAB N2 O1 HTAB N3 O2 HTAB N4 O2 HTAB O2 N1 L.S. 10 TEMP -173.00 WGHT 0.101600 4.598100 FVAR 1.27307 C1 1 0.270367 0.183179 0.537825 11.00000 0.05628 0.02003 = 0.02841 0.00433 0.01049 0.00474 C2 1 0.350497 0.163867 0.555460 11.00000 0.05789 0.03148 = 0.03392 0.00782 0.02500 0.01179 AFIX 43 H2 2 0.379226 0.111941 0.532702 11.00000 -1.20000 AFIX 0 C3 1 0.384949 0.231530 0.612134 11.00000 0.03645 0.03514 = 0.04003 0.01063 0.01407 0.00532 AFIX 43 H3 2 0.440138 0.233172 0.635202 11.00000 -1.20000 AFIX 0 C4 1 0.324118 0.294830 0.628012 11.00000 0.02880 0.02279 = 0.03260 0.01055 0.01155 0.00920 C5 1 0.326658 0.386663 0.682545 11.00000 0.02493 0.03201 = 0.01919 0.00589 -0.00220 0.00737 C6 1 0.334786 0.487157 0.639756 11.00000 0.02584 0.02714 = 0.01730 0.00186 -0.00272 0.00680 C7 1 0.401438 0.541605 0.629295 11.00000 0.02624 0.03352 = 0.02960 0.00380 0.00007 0.00517 AFIX 43 H7 2 0.455448 0.527024 0.652306 11.00000 -1.20000 AFIX 0 C8 1 0.377289 0.624140 0.578234 11.00000 0.03496 0.03112 = 0.02672 0.00152 0.00549 -0.00212 AFIX 43 H8 2 0.411878 0.674770 0.561191 11.00000 -1.20000 AFIX 0 C9 1 0.295797 0.617501 0.558223 11.00000 0.03339 0.01806 = 0.01905 -0.00338 -0.00213 0.00389 C10 1 0.237646 0.689849 0.509594 11.00000 0.04040 0.01735 = 0.02985 -0.00179 -0.00732 0.00244 C11 1 0.180613 0.630867 0.450926 11.00000 0.03416 0.01362 = 0.01937 0.00225 0.00300 -0.00179 C12 1 0.106216 0.659704 0.414212 11.00000 0.02767 0.02311 = 0.02514 0.00167 0.00637 0.00042 AFIX 43 H12 2 0.073590 0.715696 0.427339 11.00000 -1.20000 AFIX 0 C13 1 0.086637 0.591321 0.353320 11.00000 0.01891 0.02988 = 0.02478 0.00100 0.00067 -0.00172 AFIX 43 H13 2 0.038744 0.593956 0.317356 11.00000 -1.20000 AFIX 0 C14 1 0.148430 0.520449 0.354854 11.00000 0.02365 0.02676 = 0.01593 0.00195 0.00044 -0.00550 C15 1 0.156574 0.425352 0.307023 11.00000 0.02568 0.03207 = 0.01689 -0.00480 0.00004 -0.00228 C16 1 0.137793 0.327256 0.346627 11.00000 0.02627 0.02917 = 0.02415 -0.00842 0.00817 -0.00278 C17 1 0.069287 0.265679 0.336071 11.00000 0.02796 0.03043 = 0.03909 -0.01308 0.00716 -0.00524 AFIX 43 H17 2 0.022564 0.275519 0.299480 11.00000 -1.20000 AFIX 0 C18 1 0.081433 0.185547 0.389569 11.00000 0.04498 0.02893 = 0.03868 -0.01222 0.01665 -0.01010 AFIX 43 H18 2 0.043617 0.131566 0.395429 11.00000 -1.20000 AFIX 0 C19 1 0.155432 0.197122 0.431542 11.00000 0.04299 0.02395 = 0.02299 -0.00772 0.01022 -0.00093 PART 1 C20 1 0.210386 0.124837 0.482785 10.50000 0.07093 0.02148 = 0.02182 -0.00495 0.01257 -0.00646 C25 1 0.257585 0.049629 0.438190 10.50000 0.08899 0.02345 = 0.04022 -0.00748 -0.01161 0.01903 AFIX 137 H25A 2 0.295759 0.090470 0.414094 10.50000 -1.50000 H25B 2 0.219296 0.012928 0.400359 10.50000 -1.50000 H25C 2 0.287524 -0.002037 0.471937 10.50000 -1.50000 AFIX 0 C26 1 0.159890 0.061949 0.530104 10.50000 0.08392 0.03515 = 0.03661 0.00924 -0.00723 -0.01688 AFIX 137 H26A 2 0.195780 0.017712 0.565157 10.50000 -1.50000 H26B 2 0.121318 0.017254 0.497901 10.50000 -1.50000 H26C 2 0.130168 0.110528 0.557618 10.50000 -1.50000 AFIX 0 PART 2 same .01 .02 c20 > c26 C20A 1 0.197149 0.128154 0.493329 10.50000 0.07093 0.02148 = 0.02182 -0.00495 0.01257 -0.00646 C25A 1 0.229377 0.033614 0.452873 10.50000 0.10196 0.02916 = 0.03714 -0.00097 0.00765 0.01419 AFIX 137 H25D 2 0.183628 -0.004240 0.424161 10.50000 -1.50000 H25E 2 0.259604 -0.014085 0.489533 10.50000 -1.50000 H25F 2 0.265264 0.059431 0.419362 10.50000 -1.50000 AFIX 0 C26A 1 0.135223 0.090020 0.540424 10.50000 0.07077 0.05363 = 0.03877 0.00763 0.00472 -0.03527 AFIX 137 H26D 2 0.113466 0.150541 0.564094 10.50000 -1.50000 H26E 2 0.161563 0.041597 0.578697 10.50000 -1.50000 H26F 2 0.090911 0.053457 0.508697 10.50000 -1.50000 AFIX 0 PART 0 C21 1 0.401131 0.374985 0.742810 11.00000 0.03026 0.04990 = 0.03521 0.01484 -0.00610 0.00349 AFIX 137 H21A 2 0.450050 0.371229 0.719700 11.00000 -1.50000 H21B 2 0.396243 0.310407 0.771148 11.00000 -1.50000 H21C 2 0.404835 0.435833 0.776210 11.00000 -1.50000 AFIX 0 C22 1 0.188696 0.752738 0.558466 11.00000 0.05876 0.02996 = 0.04594 -0.01507 -0.02029 0.02153 AFIX 137 H22A 2 0.153390 0.802801 0.527693 11.00000 -1.50000 H22B 2 0.225820 0.791243 0.596218 11.00000 -1.50000 H22C 2 0.155516 0.704463 0.582800 11.00000 -1.50000 AFIX 0 C23 1 0.287425 0.764701 0.468706 11.00000 0.05682 0.02228 = 0.05410 0.01496 -0.02080 -0.01611 AFIX 137 H23A 2 0.320847 0.723524 0.439755 11.00000 -1.50000 H23B 2 0.322529 0.808196 0.504911 11.00000 -1.50000 H23C 2 0.250697 0.810194 0.435335 11.00000 -1.50000 AFIX 0 C24 1 0.095232 0.436321 0.234496 11.00000 0.03142 0.04582 = 0.02438 -0.00576 -0.00353 -0.00141 AFIX 137 H24A 2 0.040116 0.439878 0.246243 11.00000 -1.50000 H24B 2 0.099819 0.375270 0.202599 11.00000 -1.50000 H24C 2 0.106824 0.500777 0.208609 11.00000 -1.50000 AFIX 0 C27 1 0.253943 0.387508 0.723002 11.00000 0.02816 0.03200 = 0.01176 -0.00057 -0.00617 0.00667 C28 1 0.231056 0.479604 0.754721 11.00000 0.04356 0.03250 = 0.02793 -0.00700 0.00315 0.00216 AFIX 43 H28 2 0.258690 0.543341 0.747874 11.00000 -1.20000 AFIX 0 C29 1 0.168943 0.480424 0.796016 11.00000 0.05411 0.03826 = 0.03453 -0.00471 0.01110 0.01535 AFIX 43 H29 2 0.154059 0.544100 0.817592 11.00000 -1.20000 AFIX 0 C30 1 0.128233 0.387214 0.805831 11.00000 0.03866 0.04874 = 0.02686 0.00884 0.00664 0.01725 C31 1 0.150687 0.294981 0.775128 11.00000 0.03947 0.03883 = 0.02321 0.00823 0.00496 0.00411 AFIX 43 H31 2 0.123121 0.231201 0.782000 11.00000 -1.20000 AFIX 0 C32 1 0.213105 0.295423 0.734497 11.00000 0.03784 0.02816 = 0.01680 0.00343 -0.00030 0.00953 AFIX 43 H32 2 0.228589 0.231339 0.713868 11.00000 -1.20000 AFIX 0 C33 1 0.064126 0.386955 0.850116 11.00000 0.05167 0.05872 = 0.04590 0.01743 0.01909 0.02650 C34 1 0.239794 0.418587 0.282356 11.00000 0.02771 0.03137 = 0.01206 0.00264 0.00149 -0.00017 C35 1 0.284126 0.509014 0.273280 11.00000 0.03570 0.02564 = 0.02643 0.00597 0.00875 0.00306 AFIX 43 H35 2 0.265092 0.575492 0.287024 11.00000 -1.20000 AFIX 0 C36 1 0.355698 0.503233 0.244434 11.00000 0.03833 0.03356 = 0.03191 0.00599 0.01308 -0.00218 AFIX 43 H36 2 0.385616 0.565371 0.238389 11.00000 -1.20000 AFIX 0 C37 1 0.383180 0.406890 0.224592 11.00000 0.03196 0.04298 = 0.02402 0.00485 0.00742 -0.00186 C38 1 0.340072 0.315931 0.233571 11.00000 0.04088 0.03139 = 0.03228 -0.00504 0.01374 -0.00094 AFIX 43 H38 2 0.358958 0.249615 0.219357 11.00000 -1.20000 AFIX 0 C39 1 0.269689 0.322489 0.263246 11.00000 0.03607 0.03213 = 0.02300 -0.00396 0.00899 -0.00736 AFIX 43 H39 2 0.241012 0.259852 0.270783 11.00000 -1.20000 AFIX 0 C40 1 0.456124 0.399655 0.191879 11.00000 0.03572 0.04148 = 0.03636 -0.00479 0.01008 -0.00469 C41 1 0.025146 0.543411 0.566369 11.00000 0.03046 0.03095 = 0.02570 -0.00240 0.00503 0.00089 C42 1 0.037908 0.412762 0.479973 11.00000 0.02684 0.03127 = 0.02391 -0.00337 0.00785 -0.00102 C43 1 0.413195 0.382522 0.442108 11.00000 0.02986 0.06946 = 0.04080 -0.00008 0.01472 0.00344 AFIX 137 H43A 2 0.450904 0.437810 0.463281 11.00000 -1.50000 H43B 2 0.406815 0.385024 0.387827 11.00000 -1.50000 H43C 2 0.434650 0.313564 0.459637 11.00000 -1.50000 AFIX 0 N1 3 0.254702 0.264915 0.582237 11.00000 0.03506 0.02460 = 0.02056 0.00006 0.00307 0.00469 AFIX 43 H1N 2 0.206814 0.294106 0.581486 11.00000 -1.20000 AFIX 0 N2 3 0.270326 0.533426 0.595230 11.00000 0.02313 0.01814 = 0.02559 -0.00032 -0.00448 0.00139 AFIX 43 H2N 2 0.219707 0.512015 0.591069 11.00000 -1.20000 AFIX 0 N3 3 0.205527 0.545471 0.415015 11.00000 0.02556 0.02007 = 0.02058 0.00287 -0.00212 0.00197 AFIX 43 H3N 2 0.251466 0.511543 0.428529 11.00000 -1.20000 AFIX 0 N4 3 0.189636 0.285448 0.404131 11.00000 0.03238 0.01946 = 0.02722 -0.00286 0.00702 -0.00775 AFIX 43 H4N 2 0.238020 0.310693 0.421567 11.00000 -1.20000 AFIX 0 N5 3 0.013735 0.384428 0.885597 11.00000 0.07003 0.08943 = 0.07418 0.03607 0.04131 0.04246 N6 3 0.513319 0.393822 0.165544 11.00000 0.04342 0.06125 = 0.05841 -0.01336 0.02587 -0.00875 N7 3 0.063437 0.456831 0.546426 11.00000 0.02201 0.03277 = 0.02764 0.00115 0.00336 0.00120 O1 4 0.123162 0.416244 0.592258 11.00000 0.02667 0.03841 = 0.03451 0.00477 -0.00322 0.00623 O2 4 0.337168 0.398607 0.464546 11.00000 0.02708 0.03581 = 0.02760 0.00215 0.00448 0.00309 AFIX 147 H2O 2 0.342721 0.397114 0.511089 11.00000 -1.50000 AFIX 0 H41 2 0.047941 0.572991 0.620227 11.00000 0.02591 H42 2 0.070131 0.343405 0.465906 11.00000 0.03700 HKLF 4 REM c4pcn-pyrazine_a.res in P2(1)/n REM R1 = 0.0982 for 5433 Fo > 4sig(Fo) and 0.1226 for all 7000 data REM 508 parameters refined using 21 restraints END WGHT 0.1145 4.7232 REM Highest difference peak 0.944, deepest hole -0.261, 1-sigma level 0.089 Q1 1 0.1631 0.3955 0.5350 11.00000 0.05 0.94 Q2 1 0.3699 0.4318 0.4047 11.00000 0.05 0.72 Q3 1 0.4366 0.4632 0.4522 11.00000 0.05 0.67 Q4 1 0.2427 0.2653 0.4088 11.00000 0.05 0.66 Q5 1 0.4336 0.2569 0.6615 11.00000 0.05 0.65 Q6 1 0.4612 0.4037 0.5129 11.00000 0.05 0.61 Q7 1 0.4188 0.1748 0.6027 11.00000 0.05 0.60 Q8 1 0.2205 0.1879 0.4537 11.00000 0.05 0.59 Q9 1 0.2544 0.0371 0.5452 11.00000 0.05 0.55 Q10 1 0.2872 0.1243 0.4995 11.00000 0.05 0.54 Q11 1 0.3141 0.2830 0.5903 11.00000 0.05 0.54 Q12 1 0.3452 0.0735 0.4559 11.00000 0.05 0.53 Q13 1 0.0979 0.5362 0.3704 11.00000 0.05 0.53 Q14 1 0.3641 0.3179 0.6465 11.00000 0.05 0.51 Q15 1 0.1117 0.2392 0.3796 11.00000 0.05 0.50 Q16 1 0.4657 0.5518 0.4321 11.00000 0.05 0.50 Q17 1 0.4498 0.9021 0.4502 11.00000 0.05 0.50 Q18 1 0.3463 0.4387 0.6781 11.00000 0.05 0.49 Q19 1 0.4097 0.5948 0.6459 11.00000 0.05 0.47 Q20 1 0.3619 0.5250 0.6486 11.00000 0.05 0.47 ; _shelx_res_checksum 43078 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2704(3) 0.1832(3) 0.5378(2) 0.0345(9) Uani 1 1 d . . . . . C2 C 0.3505(3) 0.1639(3) 0.5555(2) 0.0391(10) Uani 1 1 d . . . . . H2 H 0.379226 0.111941 0.532702 0.047 Uiso 1 1 calc R U . . . C3 C 0.3849(2) 0.2315(3) 0.6121(2) 0.0363(9) Uani 1 1 d . . . . . H3 H 0.440138 0.233172 0.635202 0.044 Uiso 1 1 calc R U . . . C4 C 0.3241(2) 0.2948(3) 0.6280(2) 0.0273(8) Uani 1 1 d . . . . . C5 C 0.3267(2) 0.3867(3) 0.68254(18) 0.0260(8) Uani 1 1 d . . . . . C6 C 0.3348(2) 0.4872(3) 0.63976(18) 0.0241(7) Uani 1 1 d . . . . . C7 C 0.4014(2) 0.5416(3) 0.6293(2) 0.0303(8) Uani 1 1 d . . . . . H7 H 0.455448 0.527024 0.652306 0.036 Uiso 1 1 calc R U . . . C8 C 0.3773(2) 0.6241(3) 0.5782(2) 0.0309(8) Uani 1 1 d . . . . . H8 H 0.411878 0.674770 0.561191 0.037 Uiso 1 1 calc R U . . . C9 C 0.2958(2) 0.6175(2) 0.55822(18) 0.0242(7) Uani 1 1 d . . . . . C10 C 0.2376(2) 0.6898(3) 0.5096(2) 0.0306(8) Uani 1 1 d . . . . . C11 C 0.1806(2) 0.6309(2) 0.45093(18) 0.0225(7) Uani 1 1 d . . . . . C12 C 0.1062(2) 0.6597(3) 0.41421(18) 0.0251(7) Uani 1 1 d . . . . . H12 H 0.073590 0.715696 0.427339 0.030 Uiso 1 1 calc R U . . . C13 C 0.0866(2) 0.5913(3) 0.35332(19) 0.0248(7) Uani 1 1 d . . . . . H13 H 0.038744 0.593956 0.317356 0.030 Uiso 1 1 calc R U . . . C14 C 0.14843(19) 0.5204(3) 0.35485(17) 0.0224(7) Uani 1 1 d . . . . . C15 C 0.1566(2) 0.4254(3) 0.30702(18) 0.0253(8) Uani 1 1 d . . . . . C16 C 0.1378(2) 0.3273(3) 0.34663(19) 0.0261(8) Uani 1 1 d . . . . . C17 C 0.0693(2) 0.2657(3) 0.3361(2) 0.0323(9) Uani 1 1 d . . . . . H17 H 0.022564 0.275519 0.299480 0.039 Uiso 1 1 calc R U . . . C18 C 0.0814(2) 0.1855(3) 0.3896(2) 0.0364(9) Uani 1 1 d . . . . . H18 H 0.043617 0.131566 0.395429 0.044 Uiso 1 1 calc R U . . . C19 C 0.1554(2) 0.1971(3) 0.43154(19) 0.0294(8) Uani 1 1 d . . . . . C20 C 0.210(4) 0.1248(15) 0.483(4) 0.038(3) Uani 0.5 1 d D . P A 1 C25 C 0.2576(12) 0.0496(15) 0.4382(11) 0.053(4) Uani 0.5 1 d D U P A 1 H25A H 0.295759 0.090470 0.414094 0.080 Uiso 0.5 1 calc R U P A 1 H25B H 0.219296 0.012928 0.400359 0.080 Uiso 0.5 1 calc R U P A 1 H25C H 0.287524 -0.002037 0.471937 0.080 Uiso 0.5 1 calc R U P A 1 C26 C 0.1599(13) 0.0619(15) 0.5301(12) 0.054(4) Uani 0.5 1 d D U P A 1 H26A H 0.195780 0.017712 0.565157 0.081 Uiso 0.5 1 calc R U P A 1 H26B H 0.121318 0.017254 0.497901 0.081 Uiso 0.5 1 calc R U P A 1 H26C H 0.130168 0.110528 0.557618 0.081 Uiso 0.5 1 calc R U P A 1 C20A C 0.197(4) 0.1282(15) 0.493(4) 0.038(3) Uani 0.5 1 d D . P A 2 C25A C 0.2294(14) 0.0336(16) 0.4529(12) 0.056(4) Uani 0.5 1 d D U P A 2 H25D H 0.183628 -0.004240 0.424161 0.085 Uiso 0.5 1 calc R U P A 2 H25E H 0.259604 -0.014085 0.489533 0.085 Uiso 0.5 1 calc R U P A 2 H25F H 0.265264 0.059431 0.419362 0.085 Uiso 0.5 1 calc R U P A 2 C26A C 0.1352(13) 0.0900(15) 0.5404(12) 0.055(5) Uani 0.5 1 d D U P A 2 H26D H 0.113466 0.150541 0.564094 0.082 Uiso 0.5 1 calc R U P A 2 H26E H 0.161563 0.041597 0.578697 0.082 Uiso 0.5 1 calc R U P A 2 H26F H 0.090911 0.053457 0.508697 0.082 Uiso 0.5 1 calc R U P A 2 C21 C 0.4011(2) 0.3750(3) 0.7428(2) 0.0397(10) Uani 1 1 d . . . . . H21A H 0.450050 0.371229 0.719700 0.060 Uiso 1 1 calc R U . . . H21B H 0.396243 0.310407 0.771148 0.060 Uiso 1 1 calc R U . . . H21C H 0.404835 0.435833 0.776210 0.060 Uiso 1 1 calc R U . . . C22 C 0.1887(3) 0.7527(3) 0.5585(2) 0.0481(12) Uani 1 1 d . . . . . H22A H 0.153390 0.802801 0.527693 0.072 Uiso 1 1 calc R U . . . H22B H 0.225820 0.791243 0.596218 0.072 Uiso 1 1 calc R U . . . H22C H 0.155516 0.704463 0.582800 0.072 Uiso 1 1 calc R U . . . C23 C 0.2874(3) 0.7647(3) 0.4687(3) 0.0477(12) Uani 1 1 d . . . . . H23A H 0.320847 0.723524 0.439755 0.072 Uiso 1 1 calc R U . . . H23B H 0.322529 0.808196 0.504911 0.072 Uiso 1 1 calc R U . . . H23C H 0.250697 0.810194 0.435335 0.072 Uiso 1 1 calc R U . . . C24 C 0.0952(2) 0.4363(3) 0.2345(2) 0.0348(9) Uani 1 1 d . . . . . H24A H 0.040116 0.439878 0.246243 0.052 Uiso 1 1 calc R U . . . H24B H 0.099819 0.375270 0.202599 0.052 Uiso 1 1 calc R U . . . H24C H 0.106824 0.500777 0.208609 0.052 Uiso 1 1 calc R U . . . C27 C 0.2539(2) 0.3875(3) 0.72300(17) 0.0250(8) Uani 1 1 d . . . . . C28 C 0.2311(2) 0.4796(3) 0.7547(2) 0.0350(9) Uani 1 1 d . . . . . H28 H 0.258690 0.543341 0.747874 0.042 Uiso 1 1 calc R U . . . C29 C 0.1689(3) 0.4804(3) 0.7960(2) 0.0419(10) Uani 1 1 d . . . . . H29 H 0.154059 0.544100 0.817592 0.050 Uiso 1 1 calc R U . . . C30 C 0.1282(2) 0.3872(3) 0.8058(2) 0.0379(10) Uani 1 1 d . . . . . C31 C 0.1507(2) 0.2950(3) 0.7751(2) 0.0339(9) Uani 1 1 d . . . . . H31 H 0.123121 0.231201 0.782000 0.041 Uiso 1 1 calc R U . . . C32 C 0.2131(2) 0.2954(3) 0.73450(18) 0.0281(8) Uani 1 1 d . . . . . H32 H 0.228589 0.231339 0.713868 0.034 Uiso 1 1 calc R U . . . C33 C 0.0641(3) 0.3870(4) 0.8501(3) 0.0509(12) Uani 1 1 d . . . . . C34 C 0.2398(2) 0.4186(3) 0.28236(17) 0.0239(7) Uani 1 1 d . . . . . C35 C 0.2841(2) 0.5090(3) 0.27328(19) 0.0288(8) Uani 1 1 d . . . . . H35 H 0.265092 0.575492 0.287024 0.035 Uiso 1 1 calc R U . . . C36 C 0.3557(2) 0.5032(3) 0.2444(2) 0.0338(9) Uani 1 1 d . . . . . H36 H 0.385616 0.565371 0.238389 0.041 Uiso 1 1 calc R U . . . C37 C 0.3832(2) 0.4069(3) 0.2246(2) 0.0327(9) Uani 1 1 d . . . . . C38 C 0.3401(2) 0.3159(3) 0.2336(2) 0.0340(9) Uani 1 1 d . . . . . H38 H 0.358958 0.249615 0.219357 0.041 Uiso 1 1 calc R U . . . C39 C 0.2697(2) 0.3225(3) 0.26325(19) 0.0299(8) Uani 1 1 d . . . . . H39 H 0.241012 0.259852 0.270783 0.036 Uiso 1 1 calc R U . . . C40 C 0.4561(2) 0.3997(3) 0.1919(2) 0.0374(9) Uani 1 1 d . . . . . C41 C 0.0251(2) 0.5434(3) 0.5664(2) 0.0290(8) Uani 1 1 d . . . . . C42 C 0.0379(2) 0.4128(3) 0.47997(19) 0.0269(8) Uani 1 1 d . . . . . C43 C 0.4132(2) 0.3825(4) 0.4421(2) 0.0457(11) Uani 1 1 d . . . . . H43A H 0.450904 0.437810 0.463281 0.069 Uiso 1 1 calc R U . . . H43B H 0.406815 0.385024 0.387827 0.069 Uiso 1 1 calc R U . . . H43C H 0.434650 0.313564 0.459637 0.069 Uiso 1 1 calc R U . . . N1 N 0.25470(18) 0.2649(2) 0.58224(15) 0.0269(7) Uani 1 1 d . . . . . H1N H 0.206814 0.294106 0.581486 0.032 Uiso 1 1 calc R U . . . N2 N 0.27033(16) 0.5334(2) 0.59523(15) 0.0232(6) Uani 1 1 d . . . . . H2N H 0.219707 0.512015 0.591069 0.028 Uiso 1 1 calc R U . . . N3 N 0.20553(17) 0.5455(2) 0.41502(15) 0.0227(6) Uani 1 1 d . . . . . H3N H 0.251466 0.511543 0.428529 0.027 Uiso 1 1 calc R U . . . N4 N 0.18964(18) 0.2854(2) 0.40413(16) 0.0261(7) Uani 1 1 d . . . . . H4N H 0.238020 0.310693 0.421567 0.031 Uiso 1 1 calc R U . . . N5 N 0.0137(3) 0.3844(4) 0.8856(3) 0.0746(15) Uani 1 1 d . . . . . N6 N 0.5133(2) 0.3938(3) 0.1655(2) 0.0524(10) Uani 1 1 d . . . . . N7 N 0.06344(17) 0.4568(2) 0.54643(16) 0.0275(7) Uani 1 1 d . . . . . O1 O 0.12316(14) 0.4162(2) 0.59226(14) 0.0341(6) Uani 1 1 d . . . . . O2 O 0.33717(14) 0.3986(2) 0.46455(14) 0.0302(6) Uani 1 1 d . . . . . H2O H 0.342721 0.397114 0.511089 0.045 Uiso 1 1 calc R U . . . H41 H 0.048(2) 0.573(3) 0.620(2) 0.026(9) Uiso 1 1 d . . . . . H42 H 0.070(2) 0.343(3) 0.466(2) 0.037(10) Uiso 1 1 d . . . . . 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 C1 0.056(3) 0.0200(18) 0.028(2) 0.0043(15) 0.0105(18) 0.0047(17) C2 0.058(3) 0.031(2) 0.034(2) 0.0078(17) 0.025(2) 0.0118(19) C3 0.036(2) 0.035(2) 0.040(2) 0.0106(18) 0.0141(18) 0.0053(17) C4 0.0288(19) 0.0228(17) 0.033(2) 0.0106(15) 0.0116(16) 0.0092(14) C5 0.0249(18) 0.0320(19) 0.0192(17) 0.0059(14) -0.0022(14) 0.0074(14) C6 0.0258(18) 0.0271(18) 0.0173(16) 0.0019(14) -0.0027(14) 0.0068(14) C7 0.0262(18) 0.034(2) 0.030(2) 0.0038(16) 0.0001(15) 0.0052(15) C8 0.035(2) 0.0311(19) 0.0267(19) 0.0015(16) 0.0055(16) -0.0021(16) C9 0.0334(19) 0.0181(16) 0.0191(17) -0.0034(13) -0.0021(14) 0.0039(14) C10 0.040(2) 0.0173(17) 0.030(2) -0.0018(15) -0.0073(16) 0.0024(15) C11 0.0342(19) 0.0136(15) 0.0194(17) 0.0022(13) 0.0030(14) -0.0018(13) C12 0.0277(18) 0.0231(17) 0.0251(18) 0.0017(14) 0.0064(15) 0.0004(14) C13 0.0189(17) 0.0299(18) 0.0248(18) 0.0010(15) 0.0007(14) -0.0017(14) C14 0.0236(17) 0.0268(17) 0.0159(16) 0.0019(13) 0.0004(13) -0.0055(14) C15 0.0257(18) 0.0321(19) 0.0169(17) -0.0048(14) 0.0000(14) -0.0023(14) C16 0.0263(18) 0.0292(18) 0.0242(18) -0.0084(15) 0.0082(15) -0.0028(14) C17 0.0280(19) 0.0304(19) 0.039(2) -0.0131(17) 0.0072(17) -0.0052(15) C18 0.045(2) 0.029(2) 0.039(2) -0.0122(17) 0.0167(19) -0.0101(17) C19 0.043(2) 0.0239(18) 0.0230(18) -0.0077(15) 0.0102(16) -0.0009(16) C20 0.071(18) 0.021(2) 0.022(16) -0.005(3) 0.013(4) -0.006(4) C25 0.089(13) 0.023(7) 0.040(9) -0.007(6) -0.012(7) 0.019(7) C26 0.084(12) 0.035(8) 0.037(7) 0.009(6) -0.007(7) -0.017(7) C20A 0.071(18) 0.021(2) 0.022(16) -0.005(3) 0.013(4) -0.006(4) C25A 0.102(13) 0.029(7) 0.037(7) -0.001(5) 0.008(7) 0.014(7) C26A 0.071(11) 0.054(11) 0.039(7) 0.008(7) 0.005(7) -0.035(8) C21 0.030(2) 0.050(2) 0.035(2) 0.0148(19) -0.0061(17) 0.0035(18) C22 0.059(3) 0.030(2) 0.046(3) -0.0151(19) -0.020(2) 0.0215(19) C23 0.057(3) 0.0223(19) 0.054(3) 0.0150(18) -0.021(2) -0.0161(18) C24 0.031(2) 0.046(2) 0.0244(19) -0.0058(17) -0.0035(16) -0.0014(17) C27 0.0282(18) 0.0320(19) 0.0118(16) -0.0006(14) -0.0062(13) 0.0067(15) C28 0.044(2) 0.033(2) 0.028(2) -0.0070(16) 0.0032(17) 0.0022(17) C29 0.054(3) 0.038(2) 0.035(2) -0.0047(18) 0.011(2) 0.015(2) C30 0.039(2) 0.049(2) 0.027(2) 0.0088(18) 0.0066(17) 0.0173(19) C31 0.039(2) 0.039(2) 0.0232(19) 0.0082(16) 0.0050(16) 0.0041(17) C32 0.038(2) 0.0282(19) 0.0168(17) 0.0034(14) -0.0003(15) 0.0095(15) C33 0.052(3) 0.059(3) 0.046(3) 0.017(2) 0.019(2) 0.027(2) C34 0.0277(18) 0.0314(19) 0.0121(15) 0.0026(14) 0.0015(13) -0.0002(14) C35 0.036(2) 0.0256(18) 0.0264(19) 0.0060(15) 0.0088(16) 0.0031(15) C36 0.038(2) 0.034(2) 0.032(2) 0.0060(16) 0.0131(17) -0.0022(17) C37 0.032(2) 0.043(2) 0.0240(19) 0.0048(17) 0.0074(16) -0.0019(17) C38 0.041(2) 0.031(2) 0.032(2) -0.0050(16) 0.0137(17) -0.0009(17) C39 0.036(2) 0.032(2) 0.0230(18) -0.0040(15) 0.0090(16) -0.0074(16) C40 0.036(2) 0.041(2) 0.036(2) -0.0048(18) 0.0101(18) -0.0047(17) C41 0.0305(19) 0.0310(19) 0.0257(19) -0.0024(16) 0.0050(16) 0.0009(15) C42 0.0268(18) 0.0313(19) 0.0239(18) -0.0034(15) 0.0079(15) -0.0010(15) C43 0.030(2) 0.069(3) 0.041(2) 0.000(2) 0.0147(18) 0.003(2) N1 0.0351(17) 0.0246(15) 0.0206(15) 0.0001(12) 0.0031(13) 0.0047(13) N2 0.0231(14) 0.0181(14) 0.0256(15) -0.0003(12) -0.0045(12) 0.0014(11) N3 0.0256(15) 0.0201(14) 0.0206(14) 0.0029(11) -0.0021(12) 0.0020(11) N4 0.0324(16) 0.0195(14) 0.0272(16) -0.0029(12) 0.0070(13) -0.0078(12) N5 0.070(3) 0.089(3) 0.074(3) 0.036(3) 0.041(3) 0.042(3) N6 0.043(2) 0.061(2) 0.058(2) -0.013(2) 0.026(2) -0.0087(18) N7 0.0220(15) 0.0328(16) 0.0276(16) 0.0011(13) 0.0034(12) 0.0012(12) O1 0.0267(13) 0.0384(15) 0.0345(15) 0.0048(12) -0.0032(11) 0.0062(11) O2 0.0271(13) 0.0358(14) 0.0276(13) 0.0022(12) 0.0045(10) 0.0031(11) 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 C2 C1 N1 105.9(3) . . ? C2 C1 C20 127.0(16) . . ? N1 C1 C20 127.0(16) . . ? C2 C1 C20A 136.4(13) . . ? N1 C1 C20A 116.7(10) . . ? C1 C2 C3 109.9(3) . . ? C1 C2 H2 125.1 . . ? C3 C2 H2 125.1 . . ? C4 C3 C2 106.8(4) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? C3 C4 N1 107.1(3) . . ? C3 C4 C5 130.2(3) . . ? N1 C4 C5 122.7(3) . . ? C6 C5 C27 113.0(3) . . ? C6 C5 C21 108.8(3) . . ? C27 C5 C21 105.8(3) . . ? C6 C5 C4 107.6(3) . . ? C27 C5 C4 112.4(3) . . ? C21 C5 C4 109.2(3) . . ? C7 C6 N2 106.5(3) . . ? C7 C6 C5 130.5(3) . . ? N2 C6 C5 122.6(3) . . ? C6 C7 C8 108.5(3) . . ? C6 C7 H7 125.7 . . ? C8 C7 H7 125.7 . . ? C9 C8 C7 107.3(3) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? C8 C9 N2 107.2(3) . . ? C8 C9 C10 129.9(3) . . ? N2 C9 C10 122.8(3) . . ? C11 C10 C9 112.7(3) . . ? C11 C10 C22 109.7(3) . . ? C9 C10 C22 109.1(3) . . ? C11 C10 C23 106.9(3) . . ? C9 C10 C23 108.3(3) . . ? C22 C10 C23 110.1(3) . . ? C12 C11 N3 107.6(3) . . ? C12 C11 C10 129.4(3) . . ? N3 C11 C10 121.8(3) . . ? C11 C12 C13 107.4(3) . . ? C11 C12 H12 126.3 . . ? C13 C12 H12 126.3 . . ? C14 C13 C12 108.2(3) . . ? C14 C13 H13 125.9 . . ? C12 C13 H13 125.9 . . ? C13 C14 N3 106.8(3) . . ? C13 C14 C15 130.8(3) . . ? N3 C14 C15 122.2(3) . . ? C16 C15 C14 109.9(3) . . ? C16 C15 C34 111.5(3) . . ? C14 C15 C34 112.7(3) . . ? C16 C15 C24 109.1(3) . . ? C14 C15 C24 108.3(3) . . ? C34 C15 C24 105.1(3) . . ? N4 C16 C17 107.4(3) . . ? N4 C16 C15 122.8(3) . . ? C17 C16 C15 129.8(3) . . ? C16 C17 C18 107.0(3) . . ? C16 C17 H17 126.5 . . ? C18 C17 H17 126.5 . . ? C19 C18 C17 109.4(3) . . ? C19 C18 H18 125.3 . . ? C17 C18 H18 125.3 . . ? C18 C19 N4 106.0(3) . . ? C18 C19 C20A 129(2) . . ? N4 C19 C20A 125(2) . . ? C18 C19 C20 133.8(19) . . ? N4 C19 C20 118.0(16) . . ? C1 C20 C19 112.9(11) . . ? C1 C20 C26 105(4) . . ? C19 C20 C26 109(4) . . ? C1 C20 C25 108(4) . . ? C19 C20 C25 111(4) . . ? C26 C20 C25 110.5(10) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C20A C1 111.5(11) . . ? C19 C20A C26A 109(5) . . ? C1 C20A C26A 114(4) . . ? C19 C20A C25A 104(4) . . ? C1 C20A C25A 107(4) . . ? C26A C20A C25A 110.0(10) . . ? C20A C25A H25D 109.5 . . ? C20A C25A H25E 109.5 . . ? H25D C25A H25E 109.5 . . ? C20A C25A H25F 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? C20A C26A H26D 109.5 . . ? C20A C26A H26E 109.5 . . ? H26D C26A H26E 109.5 . . ? C20A C26A H26F 109.5 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 C22 H22A 109.5 . . ? C10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C10 C23 H23A 109.5 . . ? C10 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C10 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C24 H24A 109.5 . . ? C15 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C15 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C28 C27 C32 118.2(3) . . ? C28 C27 C5 120.3(3) . . ? C32 C27 C5 121.3(3) . . ? C29 C28 C27 121.2(4) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 119.4(4) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C31 C30 C29 120.0(4) . . ? C31 C30 C33 120.2(4) . . ? C29 C30 C33 119.8(4) . . ? C32 C31 C30 119.8(4) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C27 121.3(3) . . ? C31 C32 H32 119.3 . . ? C27 C32 H32 119.3 . . ? N5 C33 C30 178.5(5) . . ? C39 C34 C35 118.5(3) . . ? C39 C34 C15 120.4(3) . . ? C35 C34 C15 121.0(3) . . ? C36 C35 C34 120.7(3) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C37 C36 C35 119.5(3) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 C38 120.5(3) . . ? C36 C37 C40 120.4(3) . . ? C38 C37 C40 119.1(3) . . ? C39 C38 C37 119.4(3) . . ? C39 C38 H38 120.3 . . ? C37 C38 H38 120.3 . . ? C38 C39 C34 121.3(3) . . ? C38 C39 H39 119.4 . . ? C34 C39 H39 119.4 . . ? N6 C40 C37 179.5(5) . . ? N7 C41 C42 121.2(3) . 3_566 ? N7 C41 H41 115.0(19) . . ? C42 C41 H41 123.8(19) 3_566 . ? N7 C42 C41 119.5(3) . 3_566 ? N7 C42 H42 117(2) . . ? C41 C42 H42 123(2) 3_566 . ? O2 C43 H43A 109.5 . . ? O2 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O2 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C1 N1 C4 110.3(3) . . ? C1 N1 H1N 124.8 . . ? C4 N1 H1N 124.8 . . ? C9 N2 C6 110.5(3) . . ? C9 N2 H2N 124.8 . . ? C6 N2 H2N 124.8 . . ? C11 N3 C14 110.0(3) . . ? C11 N3 H3N 125.0 . . ? C14 N3 H3N 125.0 . . ? C16 N4 C19 110.3(3) . . ? C16 N4 H4N 124.9 . . ? C19 N4 H4N 124.9 . . ? O1 N7 C42 121.0(3) . . ? O1 N7 C41 119.8(3) . . ? C42 N7 C41 119.2(3) . . ? C43 O2 H2O 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.348(6) . ? C1 N1 1.368(4) . ? C1 C20 1.50(8) . ? C1 C20A 1.52(8) . ? C2 C3 1.395(6) . ? C2 H2 0.9500 . ? C3 C4 1.363(5) . ? C3 H3 0.9500 . ? C4 N1 1.369(5) . ? C4 C5 1.529(5) . ? C5 C6 1.514(5) . ? C5 C27 1.521(5) . ? C5 C21 1.529(5) . ? C6 C7 1.351(5) . ? C6 N2 1.372(4) . ? C7 C8 1.417(5) . ? C7 H7 0.9500 . ? C8 C9 1.354(5) . ? C8 H8 0.9500 . ? C9 N2 1.368(4) . ? C9 C10 1.516(5) . ? C10 C11 1.512(5) . ? C10 C22 1.530(5) . ? C10 C23 1.534(5) . ? C11 C12 1.363(5) . ? C11 N3 1.367(4) . ? C12 C13 1.407(5) . ? C12 H12 0.9500 . ? C13 C14 1.367(5) . ? C13 H13 0.9500 . ? C14 N3 1.370(4) . ? C14 C15 1.509(5) . ? C15 C16 1.499(5) . ? C15 C34 1.532(5) . ? C15 C24 1.544(5) . ? C16 N4 1.356(4) . ? C16 C17 1.374(5) . ? C17 C18 1.402(5) . ? C17 H17 0.9500 . ? C18 C19 1.353(5) . ? C18 H18 0.9500 . ? C19 N4 1.388(4) . ? C19 C20A 1.51(8) . ? C19 C20 1.51(8) . ? C20 C26 1.527(11) . ? C20 C25 1.551(10) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C20A C26A 1.527(10) . ? C20A C25A 1.551(10) . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C27 C28 1.386(5) . ? C27 C32 1.387(5) . ? C28 C29 1.378(5) . ? C28 H28 0.9500 . ? C29 C30 1.391(6) . ? C29 H29 0.9500 . ? C30 C31 1.376(5) . ? C30 C33 1.443(6) . ? C31 C32 1.374(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 N5 1.143(6) . ? C34 C39 1.384(5) . ? C34 C35 1.391(5) . ? C35 C36 1.385(5) . ? C35 H35 0.9500 . ? C36 C37 1.376(5) . ? C36 H36 0.9500 . ? C37 C38 1.385(5) . ? C37 C40 1.445(5) . ? C38 C39 1.375(5) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 N6 1.140(5) . ? C41 N7 1.351(4) . ? C41 C42 1.359(5) 3_566 ? C41 H41 1.06(4) . ? C42 N7 1.341(4) . ? C42 H42 1.08(4) . ? C43 O2 1.412(4) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? N1 H1N 0.8800 . ? N2 H2N 0.8800 . ? N3 H3N 0.8800 . ? N4 H4N 0.8800 . ? N7 O1 1.300(4) . ? O2 H2O 0.8400 . ? 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 N1 H1N O1 0.88 2.12 2.947(4) 156.8 . N2 H2N N7 0.88 2.70 3.563(4) 167.4 . N2 H2N O1 0.88 2.02 2.867(4) 160.4 . N3 H3N O2 0.88 2.06 2.914(4) 164.0 . N4 H4N O2 0.88 2.05 2.912(4) 167.7 . O2 H2O N1 0.84 2.70 3.218(4) 121.4 . 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 C1 C2 C3 1.4(4) . . . . ? C20 C1 C2 C3 -177(2) . . . . ? C20A C1 C2 C3 -167(3) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 N1 0.5(4) . . . . ? C2 C3 C4 C5 -176.9(3) . . . . ? C3 C4 C5 C6 94.7(4) . . . . ? N1 C4 C5 C6 -82.4(4) . . . . ? C3 C4 C5 C27 -140.3(4) . . . . ? N1 C4 C5 C27 42.6(4) . . . . ? C3 C4 C5 C21 -23.2(5) . . . . ? N1 C4 C5 C21 159.7(3) . . . . ? C27 C5 C6 C7 142.3(4) . . . . ? C21 C5 C6 C7 25.1(5) . . . . ? C4 C5 C6 C7 -93.0(4) . . . . ? C27 C5 C6 N2 -46.1(4) . . . . ? C21 C5 C6 N2 -163.3(3) . . . . ? C4 C5 C6 N2 78.6(4) . . . . ? N2 C6 C7 C8 1.0(4) . . . . ? C5 C6 C7 C8 173.7(3) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 N2 -0.3(4) . . . . ? C7 C8 C9 C10 175.2(3) . . . . ? C8 C9 C10 C11 131.1(4) . . . . ? N2 C9 C10 C11 -54.0(4) . . . . ? C8 C9 C10 C22 -106.8(4) . . . . ? N2 C9 C10 C22 68.1(4) . . . . ? C8 C9 C10 C23 13.1(5) . . . . ? N2 C9 C10 C23 -172.1(3) . . . . ? C9 C10 C11 C12 156.4(3) . . . . ? C22 C10 C11 C12 34.6(5) . . . . ? C23 C10 C11 C12 -84.8(4) . . . . ? C9 C10 C11 N3 -37.8(4) . . . . ? C22 C10 C11 N3 -159.6(3) . . . . ? C23 C10 C11 N3 81.0(4) . . . . ? N3 C11 C12 C13 -1.5(4) . . . . ? C10 C11 C12 C13 165.9(3) . . . . ? C11 C12 C13 C14 1.4(4) . . . . ? C12 C13 C14 N3 -0.7(4) . . . . ? C12 C13 C14 C15 174.7(3) . . . . ? C13 C14 C15 C16 -99.6(4) . . . . ? N3 C14 C15 C16 75.3(4) . . . . ? C13 C14 C15 C34 135.4(4) . . . . ? N3 C14 C15 C34 -49.7(4) . . . . ? C13 C14 C15 C24 19.5(5) . . . . ? N3 C14 C15 C24 -165.6(3) . . . . ? C14 C15 C16 N4 -74.4(4) . . . . ? C34 C15 C16 N4 51.3(4) . . . . ? C24 C15 C16 N4 167.0(3) . . . . ? C14 C15 C16 C17 103.4(4) . . . . ? C34 C15 C16 C17 -130.9(4) . . . . ? C24 C15 C16 C17 -15.2(5) . . . . ? N4 C16 C17 C18 0.4(4) . . . . ? C15 C16 C17 C18 -177.7(3) . . . . ? C16 C17 C18 C19 -0.3(4) . . . . ? C17 C18 C19 N4 0.2(4) . . . . ? C17 C18 C19 C20A -177.0(11) . . . . ? C17 C18 C19 C20 -162.1(14) . . . . ? C2 C1 C20 C19 -133.3(14) . . . . ? N1 C1 C20 C19 48.9(19) . . . . ? C2 C1 C20 C26 107.9(17) . . . . ? N1 C1 C20 C26 -70(4) . . . . ? C2 C1 C20 C25 -10(4) . . . . ? N1 C1 C20 C25 172.3(14) . . . . ? C18 C19 C20 C1 -158.1(10) . . . . ? N4 C19 C20 C1 41.3(16) . . . . ? C18 C19 C20 C26 -42(4) . . . . ? N4 C19 C20 C26 157(2) . . . . ? C18 C19 C20 C25 80(2) . . . . ? N4 C19 C20 C25 -81(3) . . . . ? C18 C19 C20A C1 -166.3(7) . . . . ? N4 C19 C20A C1 17.1(17) . . . . ? C18 C19 C20A C26A -39(3) . . . . ? N4 C19 C20A C26A 144(2) . . . . ? C18 C19 C20A C25A 78(2) . . . . ? N4 C19 C20A C25A -98(3) . . . . ? C2 C1 C20A C19 -122(2) . . . . ? N1 C1 C20A C19 70.9(16) . . . . ? C2 C1 C20A C26A 113.6(16) . . . . ? N1 C1 C20A C26A -53(4) . . . . ? C2 C1 C20A C25A -8(4) . . . . ? N1 C1 C20A C25A -175.4(17) . . . . ? C6 C5 C27 C28 -36.5(4) . . . . ? C21 C5 C27 C28 82.5(4) . . . . ? C4 C5 C27 C28 -158.5(3) . . . . ? C6 C5 C27 C32 148.9(3) . . . . ? C21 C5 C27 C32 -92.2(4) . . . . ? C4 C5 C27 C32 26.9(4) . . . . ? C32 C27 C28 C29 -0.6(5) . . . . ? C5 C27 C28 C29 -175.4(3) . . . . ? C27 C28 C29 C30 -0.2(6) . . . . ? C28 C29 C30 C31 0.7(6) . . . . ? C28 C29 C30 C33 178.9(4) . . . . ? C29 C30 C31 C32 -0.3(6) . . . . ? C33 C30 C31 C32 -178.4(4) . . . . ? C30 C31 C32 C27 -0.6(5) . . . . ? C28 C27 C32 C31 1.0(5) . . . . ? C5 C27 C32 C31 175.8(3) . . . . ? C16 C15 C34 C39 31.6(4) . . . . ? C14 C15 C34 C39 155.8(3) . . . . ? C24 C15 C34 C39 -86.4(4) . . . . ? C16 C15 C34 C35 -153.2(3) . . . . ? C14 C15 C34 C35 -29.1(4) . . . . ? C24 C15 C34 C35 88.7(4) . . . . ? C39 C34 C35 C36 1.2(5) . . . . ? C15 C34 C35 C36 -174.0(3) . . . . ? C34 C35 C36 C37 0.0(6) . . . . ? C35 C36 C37 C38 -0.3(6) . . . . ? C35 C36 C37 C40 177.7(4) . . . . ? C36 C37 C38 C39 -0.6(6) . . . . ? C40 C37 C38 C39 -178.7(3) . . . . ? C37 C38 C39 C34 1.9(6) . . . . ? C35 C34 C39 C38 -2.2(5) . . . . ? C15 C34 C39 C38 173.1(3) . . . . ? C2 C1 N1 C4 -1.1(4) . . . . ? C20 C1 N1 C4 177(2) . . . . ? C20A C1 N1 C4 170(2) . . . . ? C3 C4 N1 C1 0.4(4) . . . . ? C5 C4 N1 C1 178.0(3) . . . . ? C8 C9 N2 C6 1.0(4) . . . . ? C10 C9 N2 C6 -174.9(3) . . . . ? C7 C6 N2 C9 -1.2(4) . . . . ? C5 C6 N2 C9 -174.6(3) . . . . ? C12 C11 N3 C14 1.1(4) . . . . ? C10 C11 N3 C14 -167.5(3) . . . . ? C13 C14 N3 C11 -0.2(4) . . . . ? C15 C14 N3 C11 -176.1(3) . . . . ? C17 C16 N4 C19 -0.2(4) . . . . ? C15 C16 N4 C19 178.0(3) . . . . ? C18 C19 N4 C16 0.0(4) . . . . ? C20A C19 N4 C16 177.3(11) . . . . ? C20 C19 N4 C16 165.6(16) . . . . ? C41 C42 N7 O1 179.4(3) 3_566 . . . ? C41 C42 N7 C41 0.8(6) 3_566 . . . ? C42 C41 N7 O1 -179.4(3) 3_566 . . . ? C42 C41 N7 C42 -0.8(6) 3_566 . . . ?