#------------------------------------------------------------------------------ #$Date: 2016-05-12 09:29:01 +0300 (Thu, 12 May 2016) $ #$Revision: 182902 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225214.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_7225214 loop_ _publ_author_name 'gazzeh, houda gazzeh' 'Boudriga, Sarra' 'Askri, Moheddine' 'Khatyr, Abderrahim' 'Knorr, Michael' 'Strohman, Carsten' 'Golz, Christopher' 'Rousselin, Yoann' 'Kubicki, Marek' _publ_section_title ; Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: Microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA09703K _journal_year 2016 _chemical_formula_moiety 'C52 H42 N4 O3' _chemical_formula_sum 'C52 H42 N4 O3' _chemical_formula_weight 770.89 _chemical_name_systematic 4,4''-bis(4-methoxyphenyl)-2,2'',5,5''-tetraphenyl-2,2'',4,4''-tetrahydro-2'H,4'H-dispiro[pyrazole-3,1'-naphthalene-3',3''-pyrazol]-2'-one _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2016-03-30 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-03-31 deposited with the CCDC. 2016-05-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.682(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.5227(14) _cell_length_b 21.1915(17) _cell_length_c 15.1214(15) _cell_measurement_reflns_used 2857 _cell_measurement_temperature 173 _cell_measurement_theta_max 22.8450 _cell_measurement_theta_min 2.4090 _cell_volume 4501.8(7) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 173 _diffrn_detector_area_resol_mean 16.0560 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.1215 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 7909 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.250 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.137 _exptl_crystal_description irregular _exptl_crystal_F_000 1624 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.447 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 534 _refine_ls_number_reflns 7909 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.951 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.0736 _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^)+(0.0818P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1653 _refine_ls_wR_factor_ref 0.1906 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3888 _reflns_number_total 7909 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra09703k2.cif _cod_data_source_block 2904 _cod_database_code 7225214 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C18(H18), C38(H38) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C41(H41), C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52) 2.d Idealised Me refined as rotating group: C25(H25A,H25B,H25C), C46(H46A,H46B,H46C) ; _shelx_res_file ; 2904.res created by SHELXL-2014/7 TITL 2904 in P2(1)/n CELL 0.71073 14.522692 21.191496 15.121446 90 104.6816 90 ZERR 4 0.001408 0.001737 0.001461 0 0.0094 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 208 168 16 12 L.S. 4 PLAN 4 TEMP -100.15 MORE -1 BOND $H CONF fmap 2 acta 52 MERG 2 OMIT -3 50 OMIT 6 5 5 OMIT -2 14 3 OMIT -2 2 2 OMIT 2 2 8 OMIT -5 6 6 OMIT -2 14 5 OMIT -4 12 5 OMIT -2 4 2 OMIT 0 1 5 OMIT 3 2 7 OMIT -3 8 4 REM REM REM WGHT 0.081800 FVAR 2.00559 O1 4 0.221041 0.226113 0.748983 11.00000 0.05144 0.02683 = 0.04095 -0.00386 -0.00034 -0.00116 O2 4 0.242391 -0.143497 0.509170 11.00000 0.08364 0.02535 = 0.05071 -0.00762 0.01976 -0.00892 O3 4 0.023012 0.175120 0.174998 11.00000 0.12478 0.07018 = 0.07716 -0.00857 0.02196 -0.01133 N1 3 0.288741 0.111521 0.818002 11.00000 0.03333 0.02524 = 0.04071 0.00431 0.00410 0.00094 N2 3 0.381968 0.120513 0.813568 11.00000 0.03771 0.02430 = 0.04172 0.00020 0.00918 0.00247 N3 3 0.029892 0.232965 0.635371 11.00000 0.03800 0.02432 = 0.04284 0.00264 0.01239 0.00507 N4 3 0.050000 0.296053 0.623576 11.00000 0.04536 0.02002 = 0.04220 0.00127 0.00616 0.00313 C1 1 0.184662 0.181654 0.703271 11.00000 0.03683 0.02377 = 0.03311 0.00211 0.00830 -0.00710 C2 1 0.222977 0.114328 0.726965 11.00000 0.03535 0.02099 = 0.03327 0.00447 0.00101 -0.00285 C3 1 0.140881 0.066762 0.710880 11.00000 0.03746 0.02774 = 0.03235 -0.00054 0.01155 -0.00126 C4 1 0.141008 0.016199 0.768707 11.00000 0.05221 0.04207 = 0.03830 0.00518 -0.00186 -0.01206 AFIX 43 H4 2 0.190193 0.012267 0.823440 11.00000 -1.20000 AFIX 0 C5 1 0.069548 -0.028732 0.746972 11.00000 0.07966 0.04298 = 0.05541 0.01559 0.00555 -0.02590 AFIX 43 H5 2 0.069556 -0.063460 0.786701 11.00000 -1.20000 AFIX 0 C6 1 -0.001540 -0.022809 0.667451 11.00000 0.05244 0.04163 = 0.05422 -0.00511 0.00678 -0.02119 AFIX 43 H6 2 -0.049886 -0.054033 0.651837 11.00000 -1.20000 AFIX 0 C7 1 -0.002988 0.028014 0.610503 11.00000 0.03943 0.03242 = 0.04194 -0.00410 0.01024 -0.00676 AFIX 43 H7 2 -0.052670 0.031806 0.556122 11.00000 -1.20000 AFIX 0 C8 1 0.067775 0.073953 0.631913 11.00000 0.03667 0.02913 = 0.03278 -0.00196 0.00789 -0.00295 C9 1 0.068078 0.128356 0.569279 11.00000 0.03913 0.02989 = 0.03077 -0.00216 0.00539 -0.00376 AFIX 23 H9A 2 0.002159 0.135034 0.532064 11.00000 -1.20000 H9B 2 0.107220 0.116718 0.526866 11.00000 -1.20000 AFIX 0 C10 1 0.105362 0.190997 0.614998 11.00000 0.03620 0.02063 = 0.03559 0.00067 0.00765 0.00745 C11 1 0.267563 0.130756 0.900378 11.00000 0.04139 0.02228 = 0.03354 0.00290 0.01053 -0.00073 C12 1 0.340410 0.139023 0.979074 11.00000 0.04566 0.02354 = 0.03310 0.00443 0.00548 -0.00368 AFIX 43 H12 2 0.404757 0.134782 0.976359 11.00000 -1.20000 AFIX 0 C13 1 0.320124 0.153423 1.061658 11.00000 0.04790 0.03170 = 0.03964 0.00383 0.00430 -0.00324 AFIX 43 H13 2 0.370675 0.159134 1.114916 11.00000 -1.20000 AFIX 0 C14 1 0.227210 0.159501 1.067001 11.00000 0.05656 0.06285 = 0.04132 -0.00177 0.01511 -0.00605 AFIX 43 H14 2 0.213338 0.169051 1.123639 11.00000 -1.20000 AFIX 0 C15 1 0.154320 0.151480 0.988567 11.00000 0.04128 0.05473 = 0.04877 0.00654 0.01144 0.00193 AFIX 43 H15 2 0.090107 0.155898 0.991637 11.00000 -1.20000 AFIX 0 C16 1 0.173607 0.137168 0.906051 11.00000 0.04255 0.03821 = 0.03979 0.00727 0.00413 0.00176 AFIX 43 H16 2 0.122777 0.131667 0.852966 11.00000 -1.20000 AFIX 0 C17 1 0.387132 0.116090 0.729563 11.00000 0.03609 0.02095 = 0.04411 -0.00204 0.00693 0.00274 C18 1 0.293613 0.101190 0.663528 11.00000 0.04261 0.02219 = 0.03594 0.00210 0.00651 0.00101 AFIX 13 H18 2 0.281183 0.132681 0.612624 11.00000 -1.20000 AFIX 0 C19 1 0.288187 0.035523 0.623830 11.00000 0.03567 0.02723 = 0.03490 -0.00462 0.00278 0.00092 C20 1 0.258657 0.025172 0.530012 11.00000 0.03997 0.02376 = 0.04498 0.00162 0.00991 0.00067 AFIX 43 H20 2 0.245561 0.060353 0.489836 11.00000 -1.20000 AFIX 0 C21 1 0.248004 -0.034703 0.494142 11.00000 0.04246 0.03209 = 0.03511 -0.00234 0.00675 -0.00316 AFIX 43 H21 2 0.229929 -0.040619 0.429773 11.00000 -1.20000 AFIX 0 C22 1 0.263660 -0.086475 0.551986 11.00000 0.05163 0.02164 = 0.04611 -0.01180 0.01165 -0.00709 C23 1 0.297249 -0.078160 0.645150 11.00000 0.06551 0.02008 = 0.04497 0.00501 0.00744 0.00459 AFIX 43 H23 2 0.311533 -0.113525 0.684883 11.00000 -1.20000 AFIX 0 C24 1 0.309803 -0.017138 0.679800 11.00000 0.05758 0.02722 = 0.03657 -0.00022 0.00248 0.00949 AFIX 43 H24 2 0.333932 -0.011298 0.743789 11.00000 -1.20000 AFIX 0 C25 1 0.244153 -0.197433 0.566262 11.00000 0.09166 0.02258 = 0.06919 -0.00053 0.00937 -0.00457 AFIX 137 H25A 2 0.221421 -0.234458 0.528143 11.00000 -1.50000 H25B 2 0.202815 -0.189941 0.607336 11.00000 -1.50000 H25C 2 0.309431 -0.204897 0.602467 11.00000 -1.50000 AFIX 0 C26 1 0.476403 0.125523 0.704260 11.00000 0.04159 0.02537 = 0.04556 -0.00762 0.01203 0.00509 C27 1 0.479027 0.125174 0.612509 11.00000 0.04076 0.04775 = 0.04983 0.00204 0.00748 -0.00408 AFIX 43 H27 2 0.422992 0.115790 0.566253 11.00000 -1.20000 AFIX 0 C28 1 0.563691 0.138564 0.588597 11.00000 0.04469 0.06385 = 0.05671 0.00210 0.01620 -0.00309 AFIX 43 H28 2 0.565054 0.137693 0.526128 11.00000 -1.20000 AFIX 0 C29 1 0.645358 0.153044 0.654796 11.00000 0.04551 0.05307 = 0.07833 -0.01207 0.02812 -0.00611 AFIX 43 H29 2 0.702508 0.163194 0.638284 11.00000 -1.20000 AFIX 0 C30 1 0.642797 0.152562 0.746002 11.00000 0.04016 0.05019 = 0.07258 -0.02283 0.01872 -0.00812 AFIX 43 H30 2 0.699033 0.161747 0.792120 11.00000 -1.20000 AFIX 0 C31 1 0.559419 0.138880 0.770651 11.00000 0.04899 0.03475 = 0.05761 -0.01494 0.01497 0.00389 AFIX 43 H31 2 0.559020 0.138632 0.833377 11.00000 -1.20000 AFIX 0 C32 1 -0.012084 0.220770 0.709637 11.00000 0.03530 0.04432 = 0.03546 0.00291 0.01078 0.00442 C33 1 -0.065260 0.166703 0.709046 11.00000 0.04679 0.04189 = 0.04735 -0.00341 0.01979 -0.00344 AFIX 43 H33 2 -0.074565 0.138326 0.658920 11.00000 -1.20000 AFIX 0 C34 1 -0.104798 0.153670 0.780450 11.00000 0.04566 0.04833 = 0.06562 0.00411 0.01911 -0.00097 AFIX 43 H34 2 -0.138045 0.115165 0.781353 11.00000 -1.20000 AFIX 0 C35 1 -0.096305 0.196390 0.850818 11.00000 0.04963 0.08276 = 0.04682 0.00591 0.02157 -0.00709 AFIX 43 H35 2 -0.124941 0.187887 0.899500 11.00000 -1.20000 AFIX 0 C36 1 -0.046189 0.251360 0.850198 11.00000 0.07306 0.07314 = 0.03931 -0.01553 0.01985 -0.01424 AFIX 43 H36 2 -0.040893 0.281011 0.898350 11.00000 -1.20000 AFIX 0 C37 1 -0.003684 0.263814 0.780571 11.00000 0.04916 0.04294 = 0.03733 -0.00903 0.01008 -0.00722 AFIX 43 H37 2 0.031325 0.301724 0.780930 11.00000 -1.20000 AFIX 0 C38 1 0.145594 0.236654 0.551284 11.00000 0.03827 0.02253 = 0.03499 -0.00026 0.00900 0.00257 AFIX 13 H38 2 0.216737 0.235144 0.569111 11.00000 -1.20000 AFIX 0 C39 1 0.112476 0.300313 0.576855 11.00000 0.03674 0.02222 = 0.03540 -0.00072 0.00642 0.00377 C40 1 0.109714 0.223148 0.449736 11.00000 0.05487 0.01950 = 0.03695 0.00437 0.00796 0.00003 C41 1 0.169385 0.197227 0.400765 11.00000 0.07937 0.03083 = 0.03913 -0.00155 0.02414 -0.00335 AFIX 43 H41 2 0.234225 0.190254 0.431470 11.00000 -1.20000 AFIX 0 C42 1 0.139708 0.181496 0.311778 11.00000 0.09236 0.05386 = 0.06206 0.00485 0.02711 -0.00867 AFIX 43 H42 2 0.182390 0.163227 0.280705 11.00000 -1.20000 AFIX 0 C43 1 0.047427 0.192337 0.267496 11.00000 0.13594 0.03369 = 0.02196 -0.00458 0.02863 -0.01941 C44 1 -0.018248 0.219191 0.310786 11.00000 0.08189 0.03216 = 0.05038 0.01658 -0.01526 -0.01221 AFIX 43 H44 2 -0.082550 0.226581 0.278673 11.00000 -1.20000 AFIX 0 C45 1 0.016009 0.234709 0.404568 11.00000 0.06819 0.03201 = 0.04384 0.00557 0.00024 -0.00185 AFIX 43 H45 2 -0.025726 0.253166 0.436534 11.00000 -1.20000 AFIX 0 C46 1 -0.067962 0.191617 0.128961 11.00000 0.10668 0.07324 = 0.12162 0.02686 -0.01902 -0.01256 AFIX 137 H46A 2 -0.079476 0.178979 0.064742 11.00000 -1.50000 H46B 2 -0.075747 0.237402 0.132619 11.00000 -1.50000 H46C 2 -0.113580 0.170242 0.156673 11.00000 -1.50000 AFIX 0 C47 1 0.142947 0.360905 0.547601 11.00000 0.04131 0.02705 = 0.03434 -0.00010 0.00564 0.00456 C48 1 0.101730 0.416986 0.567363 11.00000 0.04472 0.03239 = 0.04059 -0.00240 0.00628 0.00265 AFIX 43 H48 2 0.054110 0.415834 0.600348 11.00000 -1.20000 AFIX 0 C49 1 0.130303 0.474609 0.538805 11.00000 0.05281 0.01973 = 0.05430 -0.00992 -0.00399 -0.00550 AFIX 43 H49 2 0.101020 0.512553 0.551149 11.00000 -1.20000 AFIX 0 C50 1 0.200757 0.476821 0.492790 11.00000 0.06460 0.02881 = 0.05429 0.00273 0.01675 -0.00826 AFIX 43 H50 2 0.220853 0.516296 0.474488 11.00000 -1.20000 AFIX 0 C51 1 0.242206 0.421714 0.473236 11.00000 0.07106 0.02666 = 0.07416 -0.00107 0.02905 -0.00770 AFIX 43 H51 2 0.290703 0.423031 0.441296 11.00000 -1.20000 AFIX 0 C52 1 0.212529 0.364439 0.500558 11.00000 0.05440 0.03087 = 0.06342 0.00211 0.02509 0.00415 AFIX 43 H52 2 0.240921 0.326611 0.486474 11.00000 -1.20000 AFIX 0 HKLF 4 REM 2904 in P2(1)/n REM R1 = 0.0736 for 3888 Fo > 4sig(Fo) and 0.1387 for all 7909 data REM 534 parameters refined using 0 restraints END WGHT 0.0818 0.0000 REM Highest difference peak 0.447, deepest hole -0.311, 1-sigma level 0.054 Q1 1 -0.0450 0.1943 0.1926 11.00000 0.05 0.45 Q2 1 0.0047 0.1825 0.0966 11.00000 0.05 0.44 Q3 1 0.2436 0.0157 0.2525 11.00000 0.05 0.35 Q4 1 -0.0803 0.2251 0.3201 11.00000 0.05 0.33 ; _shelx_res_checksum 67463 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' _solvent_exptl_crystal_recrystallization_method Chloroform/Ethanol 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 O1 O 0.22104(17) 0.22611(11) 0.74898(16) 0.0419(6) Uani 1 1 d . O2 O 0.24239(18) -0.14350(11) 0.50917(17) 0.0527(7) Uani 1 1 d . O3 O 0.0230(3) 0.17512(16) 0.1750(2) 0.0914(11) Uani 1 1 d . N1 N 0.28874(18) 0.11152(13) 0.81800(19) 0.0340(7) Uani 1 1 d . N2 N 0.38197(19) 0.12051(12) 0.8136(2) 0.0347(7) Uani 1 1 d . N3 N 0.02989(19) 0.23297(13) 0.63537(19) 0.0347(7) Uani 1 1 d . N4 N 0.0500(2) 0.29605(13) 0.62358(19) 0.0368(7) Uani 1 1 d . C1 C 0.1847(2) 0.18165(16) 0.7033(2) 0.0313(8) Uani 1 1 d . C2 C 0.2230(2) 0.11433(15) 0.7270(2) 0.0313(8) Uani 1 1 d . C3 C 0.1409(2) 0.06676(16) 0.7109(2) 0.0320(8) Uani 1 1 d . C4 C 0.1410(3) 0.01620(18) 0.7687(3) 0.0466(10) Uani 1 1 d . H4 H 0.1902 0.0123 0.8234 0.056 Uiso 1 1 calc R C5 C 0.0695(3) -0.02873(19) 0.7470(3) 0.0614(12) Uani 1 1 d . H5 H 0.0696 -0.0635 0.7867 0.074 Uiso 1 1 calc R C6 C -0.0015(3) -0.02281(19) 0.6675(3) 0.0506(11) Uani 1 1 d . H6 H -0.0499 -0.0540 0.6518 0.061 Uiso 1 1 calc R C7 C -0.0030(2) 0.02801(17) 0.6105(2) 0.0379(9) Uani 1 1 d . H7 H -0.0527 0.0318 0.5561 0.046 Uiso 1 1 calc R C8 C 0.0678(2) 0.07395(16) 0.6319(2) 0.0330(8) Uani 1 1 d . C9 C 0.0681(2) 0.12836(16) 0.5693(2) 0.0339(8) Uani 1 1 d . H9A H 0.0022 0.1350 0.5321 0.041 Uiso 1 1 calc R H9B H 0.1072 0.1167 0.5269 0.041 Uiso 1 1 calc R C10 C 0.1054(2) 0.19100(15) 0.6150(2) 0.0311(8) Uani 1 1 d . C11 C 0.2676(2) 0.13076(15) 0.9004(2) 0.0322(8) Uani 1 1 d . C12 C 0.3404(3) 0.13902(15) 0.9791(2) 0.0349(9) Uani 1 1 d . H12 H 0.4048 0.1348 0.9764 0.042 Uiso 1 1 calc R C13 C 0.3201(3) 0.15342(16) 1.0617(3) 0.0410(9) Uani 1 1 d . H13 H 0.3707 0.1591 1.1149 0.049 Uiso 1 1 calc R C14 C 0.2272(3) 0.1595(2) 1.0670(3) 0.0531(11) Uani 1 1 d . H14 H 0.2133 0.1691 1.1236 0.064 Uiso 1 1 calc R C15 C 0.1543(3) 0.15148(18) 0.9886(3) 0.0483(10) Uani 1 1 d . H15 H 0.0901 0.1559 0.9916 0.058 Uiso 1 1 calc R C16 C 0.1736(3) 0.13717(17) 0.9061(2) 0.0413(9) Uani 1 1 d . H16 H 0.1228 0.1317 0.8530 0.050 Uiso 1 1 calc R C17 C 0.3871(2) 0.11609(15) 0.7296(3) 0.0343(8) Uani 1 1 d . C18 C 0.2936(2) 0.10119(15) 0.6635(2) 0.0342(8) Uani 1 1 d . H18 H 0.2812 0.1327 0.6126 0.041 Uiso 1 1 calc R C19 C 0.2882(2) 0.03552(16) 0.6238(2) 0.0337(8) Uani 1 1 d . C20 C 0.2587(2) 0.02517(16) 0.5300(2) 0.0364(9) Uani 1 1 d . H20 H 0.2456 0.0604 0.4898 0.044 Uiso 1 1 calc R C21 C 0.2480(2) -0.03470(17) 0.4941(2) 0.0371(9) Uani 1 1 d . H21 H 0.2299 -0.0406 0.4298 0.045 Uiso 1 1 calc R C22 C 0.2637(2) -0.08648(16) 0.5520(3) 0.0399(9) Uani 1 1 d . C23 C 0.2972(3) -0.07816(16) 0.6451(3) 0.0447(10) Uani 1 1 d . H23 H 0.3115 -0.1135 0.6849 0.054 Uiso 1 1 calc R C24 C 0.3098(3) -0.01714(17) 0.6798(2) 0.0422(9) Uani 1 1 d . H24 H 0.3339 -0.0113 0.7438 0.051 Uiso 1 1 calc R C25 C 0.2442(3) -0.19743(18) 0.5663(3) 0.0631(12) Uani 1 1 d . H25A H 0.2214 -0.2345 0.5281 0.095 Uiso 1 1 calc GR H25B H 0.2028 -0.1899 0.6073 0.095 Uiso 1 1 calc GR H25C H 0.3094 -0.2049 0.6025 0.095 Uiso 1 1 calc GR C26 C 0.4764(2) 0.12552(16) 0.7043(2) 0.0373(9) Uani 1 1 d . C27 C 0.4790(3) 0.12517(18) 0.6125(3) 0.0468(10) Uani 1 1 d . H27 H 0.4230 0.1158 0.5663 0.056 Uiso 1 1 calc R C28 C 0.5637(3) 0.1386(2) 0.5886(3) 0.0545(11) Uani 1 1 d . H28 H 0.5651 0.1377 0.5261 0.065 Uiso 1 1 calc R C29 C 0.6454(3) 0.15304(19) 0.6548(3) 0.0567(12) Uani 1 1 d . H29 H 0.7025 0.1632 0.6383 0.068 Uiso 1 1 calc R C30 C 0.6428(3) 0.15256(19) 0.7460(3) 0.0535(11) Uani 1 1 d . H30 H 0.6990 0.1617 0.7921 0.064 Uiso 1 1 calc R C31 C 0.5594(3) 0.13888(17) 0.7707(3) 0.0469(10) Uani 1 1 d . H31 H 0.5590 0.1386 0.8334 0.056 Uiso 1 1 calc R C32 C -0.0121(2) 0.22077(18) 0.7096(2) 0.0380(9) Uani 1 1 d . C33 C -0.0653(2) 0.16670(18) 0.7090(3) 0.0439(10) Uani 1 1 d . H33 H -0.0746 0.1383 0.6589 0.053 Uiso 1 1 calc R C34 C -0.1048(3) 0.1537(2) 0.7805(3) 0.0523(11) Uani 1 1 d . H34 H -0.1380 0.1152 0.7814 0.063 Uiso 1 1 calc R C35 C -0.0963(3) 0.1964(2) 0.8508(3) 0.0581(12) Uani 1 1 d . H35 H -0.1249 0.1879 0.8995 0.070 Uiso 1 1 calc R C36 C -0.0462(3) 0.2514(2) 0.8502(3) 0.0608(12) Uani 1 1 d . H36 H -0.0409 0.2810 0.8984 0.073 Uiso 1 1 calc R C37 C -0.0037(3) 0.26381(18) 0.7806(2) 0.0433(10) Uani 1 1 d . H37 H 0.0313 0.3017 0.7809 0.052 Uiso 1 1 calc R C38 C 0.1456(2) 0.23665(15) 0.5513(2) 0.0320(8) Uani 1 1 d . H38 H 0.2167 0.2351 0.5691 0.038 Uiso 1 1 calc R C39 C 0.1125(2) 0.30031(15) 0.5769(2) 0.0319(8) Uani 1 1 d . C40 C 0.1097(3) 0.22315(15) 0.4497(2) 0.0378(9) Uani 1 1 d . C41 C 0.1694(3) 0.19723(17) 0.4008(3) 0.0481(10) Uani 1 1 d . H41 H 0.2342 0.1903 0.4315 0.058 Uiso 1 1 calc R C42 C 0.1397(4) 0.1815(2) 0.3118(3) 0.0681(13) Uani 1 1 d . H42 H 0.1824 0.1632 0.2807 0.082 Uiso 1 1 calc R C43 C 0.0474(4) 0.19234(19) 0.2675(3) 0.0623(14) Uani 1 1 d . C44 C -0.0182(3) 0.21919(18) 0.3108(3) 0.0606(13) Uani 1 1 d . H44 H -0.0825 0.2266 0.2787 0.073 Uiso 1 1 calc R C45 C 0.0160(3) 0.23471(18) 0.4046(3) 0.0505(11) Uani 1 1 d . H45 H -0.0257 0.2532 0.4365 0.061 Uiso 1 1 calc R C46 C -0.0680(4) 0.1916(3) 0.1290(4) 0.109(2) Uani 1 1 d . H46A H -0.0795 0.1790 0.0647 0.164 Uiso 1 1 calc GR H46B H -0.0757 0.2374 0.1326 0.164 Uiso 1 1 calc GR H46C H -0.1136 0.1702 0.1567 0.164 Uiso 1 1 calc GR C47 C 0.1429(2) 0.36091(16) 0.5476(2) 0.0349(8) Uani 1 1 d . C48 C 0.1017(2) 0.41699(16) 0.5674(2) 0.0401(9) Uani 1 1 d . H48 H 0.0541 0.4158 0.6003 0.048 Uiso 1 1 calc R C49 C 0.1303(3) 0.47461(17) 0.5388(3) 0.0455(10) Uani 1 1 d . H49 H 0.1010 0.5126 0.5511 0.055 Uiso 1 1 calc R C50 C 0.2008(3) 0.47682(18) 0.4928(3) 0.0489(10) Uani 1 1 d . H50 H 0.2209 0.5163 0.4745 0.059 Uiso 1 1 calc R C51 C 0.2422(3) 0.42171(18) 0.4732(3) 0.0554(11) Uani 1 1 d . H51 H 0.2907 0.4230 0.4413 0.066 Uiso 1 1 calc R C52 C 0.2125(3) 0.36444(18) 0.5006(3) 0.0477(10) Uani 1 1 d . H52 H 0.2409 0.3266 0.4865 0.057 Uiso 1 1 calc R 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 0.0514(16) 0.0268(14) 0.0410(15) -0.0039(12) -0.0003(12) -0.0012(12) O2 0.084(2) 0.0253(15) 0.0507(16) -0.0076(13) 0.0198(15) -0.0089(13) O3 0.125(3) 0.070(3) 0.077(3) -0.009(2) 0.022(2) -0.011(2) N1 0.0333(17) 0.0252(17) 0.0407(18) 0.0043(14) 0.0041(14) 0.0009(12) N2 0.0377(18) 0.0243(17) 0.0417(19) 0.0002(14) 0.0092(14) 0.0025(13) N3 0.0380(17) 0.0243(17) 0.0428(18) 0.0026(14) 0.0124(14) 0.0051(13) N4 0.0454(18) 0.0200(16) 0.0422(18) 0.0013(14) 0.0062(15) 0.0031(13) C1 0.037(2) 0.024(2) 0.033(2) 0.0021(16) 0.0083(17) -0.0071(16) C2 0.0353(19) 0.0210(19) 0.033(2) 0.0045(15) 0.0010(16) -0.0029(15) C3 0.037(2) 0.028(2) 0.032(2) -0.0005(16) 0.0115(16) -0.0013(15) C4 0.052(2) 0.042(2) 0.038(2) 0.0052(19) -0.0019(19) -0.0121(19) C5 0.080(3) 0.043(3) 0.055(3) 0.016(2) 0.006(2) -0.026(2) C6 0.052(2) 0.042(3) 0.054(3) -0.005(2) 0.007(2) -0.0212(19) C7 0.039(2) 0.032(2) 0.042(2) -0.0041(18) 0.0102(18) -0.0068(17) C8 0.037(2) 0.029(2) 0.033(2) -0.0020(16) 0.0079(17) -0.0030(16) C9 0.039(2) 0.030(2) 0.0308(19) -0.0022(16) 0.0054(16) -0.0038(16) C10 0.0362(19) 0.0206(19) 0.036(2) 0.0007(15) 0.0077(16) 0.0074(15) C11 0.041(2) 0.0223(19) 0.034(2) 0.0029(16) 0.0105(17) -0.0007(15) C12 0.046(2) 0.024(2) 0.033(2) 0.0044(16) 0.0055(18) -0.0037(16) C13 0.048(2) 0.032(2) 0.040(2) 0.0038(18) 0.0043(19) -0.0032(17) C14 0.057(3) 0.063(3) 0.041(2) -0.002(2) 0.015(2) -0.006(2) C15 0.041(2) 0.055(3) 0.049(3) 0.007(2) 0.011(2) 0.0019(19) C16 0.043(2) 0.038(2) 0.040(2) 0.0073(18) 0.0041(18) 0.0018(17) C17 0.036(2) 0.021(2) 0.044(2) -0.0020(17) 0.0069(18) 0.0027(15) C18 0.043(2) 0.0222(19) 0.036(2) 0.0021(16) 0.0065(17) 0.0010(16) C19 0.036(2) 0.027(2) 0.035(2) -0.0046(17) 0.0028(17) 0.0009(16) C20 0.040(2) 0.024(2) 0.045(2) 0.0016(17) 0.0099(18) 0.0007(16) C21 0.042(2) 0.032(2) 0.035(2) -0.0023(17) 0.0067(17) -0.0032(16) C22 0.052(2) 0.022(2) 0.046(2) -0.0118(18) 0.0116(19) -0.0071(17) C23 0.066(3) 0.020(2) 0.045(2) 0.0050(18) 0.007(2) 0.0046(18) C24 0.058(2) 0.027(2) 0.037(2) -0.0002(17) 0.0025(19) 0.0095(17) C25 0.092(3) 0.023(2) 0.069(3) -0.001(2) 0.009(3) -0.005(2) C26 0.042(2) 0.025(2) 0.046(2) -0.0076(17) 0.0120(19) 0.0051(16) C27 0.041(2) 0.048(3) 0.050(3) 0.002(2) 0.0075(19) -0.0041(18) C28 0.045(3) 0.064(3) 0.057(3) 0.002(2) 0.016(2) -0.003(2) C29 0.046(3) 0.053(3) 0.078(3) -0.012(2) 0.028(2) -0.006(2) C30 0.040(2) 0.050(3) 0.073(3) -0.023(2) 0.019(2) -0.0081(19) C31 0.049(2) 0.035(2) 0.058(3) -0.015(2) 0.015(2) 0.0039(18) C32 0.035(2) 0.044(2) 0.035(2) 0.0029(18) 0.0108(17) 0.0044(17) C33 0.047(2) 0.042(2) 0.047(2) -0.0034(19) 0.020(2) -0.0034(18) C34 0.046(2) 0.048(3) 0.066(3) 0.004(2) 0.019(2) -0.0010(19) C35 0.050(3) 0.083(4) 0.047(3) 0.006(2) 0.022(2) -0.007(2) C36 0.073(3) 0.073(3) 0.039(3) -0.016(2) 0.020(2) -0.014(3) C37 0.049(2) 0.043(2) 0.037(2) -0.0090(19) 0.0101(19) -0.0072(18) C38 0.038(2) 0.0225(19) 0.035(2) -0.0003(16) 0.0090(16) 0.0026(15) C39 0.037(2) 0.0222(19) 0.035(2) -0.0007(16) 0.0064(17) 0.0038(16) C40 0.055(2) 0.0195(19) 0.037(2) 0.0044(16) 0.008(2) 0.0000(17) C41 0.079(3) 0.031(2) 0.039(2) -0.0015(18) 0.024(2) -0.003(2) C42 0.092(4) 0.054(3) 0.062(3) 0.005(3) 0.027(3) -0.009(3) C43 0.136(5) 0.034(3) 0.022(2) -0.0046(19) 0.029(3) -0.019(3) C44 0.082(3) 0.032(2) 0.050(3) 0.017(2) -0.015(3) -0.012(2) C45 0.068(3) 0.032(2) 0.044(2) 0.0056(19) 0.000(2) -0.002(2) C46 0.107(5) 0.073(4) 0.122(5) 0.027(4) -0.019(4) -0.013(3) C47 0.041(2) 0.027(2) 0.034(2) -0.0001(17) 0.0056(17) 0.0046(16) C48 0.045(2) 0.032(2) 0.041(2) -0.0024(18) 0.0063(18) 0.0027(18) C49 0.053(2) 0.020(2) 0.054(3) -0.0099(18) -0.004(2) -0.0055(17) C50 0.065(3) 0.029(2) 0.054(3) 0.0027(19) 0.017(2) -0.008(2) C51 0.071(3) 0.027(2) 0.074(3) -0.001(2) 0.029(2) -0.008(2) C52 0.054(2) 0.031(2) 0.063(3) 0.002(2) 0.025(2) 0.0042(18) 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 C22 O2 C25 116.9(3) C46 O3 C43 114.0(4) N2 N1 C2 111.2(3) N2 N1 C11 115.8(3) C11 N1 C2 125.4(3) C17 N2 N1 109.7(3) N4 N3 C10 110.8(3) N4 N3 C32 114.8(3) C32 N3 C10 122.1(3) C39 N4 N3 109.8(3) O1 C1 C2 120.6(3) O1 C1 C10 121.2(3) C10 C1 C2 117.9(3) N1 C2 C1 111.6(3) N1 C2 C3 114.7(3) N1 C2 C18 101.1(2) C1 C2 C18 105.7(2) C3 C2 C1 110.6(3) C3 C2 C18 112.5(3) C4 C3 C2 122.2(3) C4 C3 C8 120.4(3) C8 C3 C2 117.3(3) C3 C4 H4 119.9 C3 C4 C5 120.1(4) C5 C4 H4 119.9 C4 C5 H5 120.2 C6 C5 C4 119.7(4) C6 C5 H5 120.2 C5 C6 H6 119.8 C7 C6 C5 120.5(4) C7 C6 H6 119.8 C6 C7 H7 119.7 C6 C7 C8 120.6(3) C8 C7 H7 119.7 C3 C8 C7 118.7(3) C3 C8 C9 120.3(3) C7 C8 C9 120.9(3) C8 C9 H9A 108.2 C8 C9 H9B 108.2 C8 C9 C10 116.2(3) H9A C9 H9B 107.4 C10 C9 H9A 108.2 C10 C9 H9B 108.2 N3 C10 C1 108.8(3) N3 C10 C9 114.4(3) N3 C10 C38 99.5(2) C1 C10 C38 107.3(3) C9 C10 C1 112.4(3) C9 C10 C38 113.5(3) C12 C11 N1 120.1(3) C12 C11 C16 118.7(3) C16 C11 N1 121.0(3) C11 C12 H12 119.7 C13 C12 C11 120.6(3) C13 C12 H12 119.7 C12 C13 H13 119.7 C14 C13 C12 120.5(4) C14 C13 H13 119.7 C13 C14 H14 120.5 C13 C14 C15 119.0(4) C15 C14 H14 120.5 C14 C15 H15 119.5 C16 C15 C14 121.0(4) C16 C15 H15 119.5 C11 C16 H16 119.9 C15 C16 C11 120.2(3) C15 C16 H16 119.9 N2 C17 C18 113.6(3) N2 C17 C26 121.7(3) C26 C17 C18 124.7(3) C2 C18 H18 109.1 C17 C18 C2 100.0(3) C17 C18 H18 109.1 C17 C18 C19 113.9(3) C19 C18 C2 115.0(3) C19 C18 H18 109.1 C20 C19 C18 121.5(3) C24 C19 C18 121.2(3) C24 C19 C20 117.3(3) C19 C20 H20 119.2 C21 C20 C19 121.5(3) C21 C20 H20 119.2 C20 C21 H21 120.1 C20 C21 C22 119.9(3) C22 C21 H21 120.1 O2 C22 C21 114.8(3) O2 C22 C23 125.1(3) C23 C22 C21 120.1(3) C22 C23 H23 120.6 C22 C23 C24 118.8(3) C24 C23 H23 120.6 C19 C24 C23 122.0(3) C19 C24 H24 119.0 C23 C24 H24 119.0 O2 C25 H25A 109.5 O2 C25 H25B 109.5 O2 C25 H25C 109.5 H25A C25 H25B 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C27 C26 C17 120.7(3) C31 C26 C17 120.4(3) C31 C26 C27 118.8(3) C26 C27 H27 119.9 C28 C27 C26 120.2(4) C28 C27 H27 119.9 C27 C28 H28 119.7 C29 C28 C27 120.6(4) C29 C28 H28 119.7 C28 C29 H29 120.5 C28 C29 C30 119.0(4) C30 C29 H29 120.5 C29 C30 H30 119.5 C31 C30 C29 120.9(4) C31 C30 H30 119.5 C26 C31 H31 119.8 C30 C31 C26 120.4(4) C30 C31 H31 119.8 C33 C32 N3 119.6(3) C33 C32 C37 119.3(3) C37 C32 N3 121.1(3) C32 C33 H33 119.8 C34 C33 C32 120.4(4) C34 C33 H33 119.8 C33 C34 H34 120.0 C33 C34 C35 120.1(4) C35 C34 H34 120.0 C34 C35 H35 120.2 C36 C35 C34 119.7(4) C36 C35 H35 120.2 C35 C36 H36 119.7 C37 C36 C35 120.6(4) C37 C36 H36 119.7 C32 C37 H37 120.1 C36 C37 C32 119.8(4) C36 C37 H37 120.1 C10 C38 H38 109.4 C39 C38 C10 101.5(3) C39 C38 H38 109.4 C39 C38 C40 112.1(3) C40 C38 C10 114.6(3) C40 C38 H38 109.4 N4 C39 C38 113.0(3) N4 C39 C47 122.5(3) C47 C39 C38 124.4(3) C41 C40 C38 120.9(3) C45 C40 C38 120.6(3) C45 C40 C41 118.5(3) C40 C41 H41 118.4 C42 C41 C40 123.1(4) C42 C41 H41 118.4 C41 C42 H42 120.8 C41 C42 C43 118.5(4) C43 C42 H42 120.8 O3 C43 C44 122.7(5) C42 C43 O3 114.6(5) C42 C43 C44 122.7(4) C43 C44 H44 121.6 C43 C44 C45 116.9(4) C45 C44 H44 121.6 C40 C45 C44 120.4(4) C40 C45 H45 119.8 C44 C45 H45 119.8 O3 C46 H46A 109.5 O3 C46 H46B 109.5 O3 C46 H46C 109.5 H46A C46 H46B 109.5 H46A C46 H46C 109.5 H46B C46 H46C 109.5 C48 C47 C39 120.2(3) C52 C47 C39 121.4(3) C52 C47 C48 118.3(3) C47 C48 H48 119.9 C49 C48 C47 120.1(4) C49 C48 H48 119.9 C48 C49 H49 119.8 C50 C49 C48 120.3(4) C50 C49 H49 119.8 C49 C50 H50 120.0 C49 C50 C51 120.0(4) C51 C50 H50 120.0 C50 C51 H51 120.3 C50 C51 C52 119.5(4) C52 C51 H51 120.3 C47 C52 C51 121.7(4) C47 C52 H52 119.1 C51 C52 H52 119.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.208(4) O2 C22 1.369(4) O2 C25 1.429(4) O3 C43 1.401(5) O3 C46 1.373(6) N1 N2 1.386(4) N1 C2 1.464(4) N1 C11 1.417(4) N2 C17 1.295(4) N3 N4 1.390(4) N3 C10 1.503(4) N3 C32 1.431(4) N4 C39 1.287(4) C1 C2 1.540(4) C1 C10 1.539(4) C2 C3 1.533(4) C2 C18 1.596(5) C3 C4 1.383(5) C3 C8 1.391(4) C4 H4 0.9500 C4 C5 1.385(5) C5 H5 0.9500 C5 C6 1.378(5) C6 H6 0.9500 C6 C7 1.376(5) C7 H7 0.9500 C7 C8 1.393(5) C8 C9 1.493(5) C9 H9A 0.9900 C9 H9B 0.9900 C9 C10 1.531(4) C10 C38 1.578(4) C11 C12 1.388(4) C11 C16 1.395(5) C12 H12 0.9500 C12 C13 1.388(5) C13 H13 0.9500 C13 C14 1.378(5) C14 H14 0.9500 C14 C15 1.386(5) C15 H15 0.9500 C15 C16 1.380(5) C16 H16 0.9500 C17 C18 1.501(4) C17 C26 1.456(5) C18 H18 1.0000 C18 C19 1.510(4) C19 C20 1.391(4) C19 C24 1.388(5) C20 H20 0.9500 C20 C21 1.373(5) C21 H21 0.9500 C21 C22 1.386(5) C22 C23 1.380(5) C23 H23 0.9500 C23 C24 1.390(5) C24 H24 0.9500 C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 C26 C27 1.398(5) C26 C31 1.389(5) C27 H27 0.9500 C27 C28 1.396(5) C28 H28 0.9500 C28 C29 1.379(5) C29 H29 0.9500 C29 C30 1.389(5) C30 H30 0.9500 C30 C31 1.385(5) C31 H31 0.9500 C32 C33 1.380(5) C32 C37 1.390(5) C33 H33 0.9500 C33 C34 1.373(5) C34 H34 0.9500 C34 C35 1.379(5) C35 H35 0.9500 C35 C36 1.375(6) C36 H36 0.9500 C36 C37 1.374(5) C37 H37 0.9500 C38 H38 1.0000 C38 C39 1.515(4) C38 C40 1.518(5) C39 C47 1.463(5) C40 C41 1.388(5) C40 C45 1.381(5) C41 H41 0.9500 C41 C42 1.347(5) C42 H42 0.9500 C42 C43 1.357(6) C43 C44 1.407(6) C44 H44 0.9500 C44 C45 1.417(5) C45 H45 0.9500 C46 H46A 0.9800 C46 H46B 0.9800 C46 H46C 0.9800 C47 C48 1.397(5) C47 C52 1.377(5) C48 H48 0.9500 C48 C49 1.393(5) C49 H49 0.9500 C49 C50 1.376(5) C50 H50 0.9500 C50 C51 1.380(5) C51 H51 0.9500 C51 C52 1.386(5) C52 H52 0.9500 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 O1 C1 C2 N1 13.0(4) O1 C1 C2 C3 141.9(3) O1 C1 C2 C18 -96.0(3) O1 C1 C10 N3 -50.9(4) O1 C1 C10 C9 -178.7(3) O1 C1 C10 C38 55.8(4) O2 C22 C23 C24 -175.7(3) O3 C43 C44 C45 -179.7(3) N1 N2 C17 C18 -1.5(4) N1 N2 C17 C26 178.0(3) N1 C2 C3 C4 -14.3(5) N1 C2 C3 C8 169.6(3) N1 C2 C18 C17 -18.8(3) N1 C2 C18 C19 103.7(3) N1 C11 C12 C13 -175.3(3) N1 C11 C16 C15 175.3(3) N2 N1 C2 C1 -91.9(3) N2 N1 C2 C3 141.4(3) N2 N1 C2 C18 20.1(3) N2 N1 C11 C12 -19.0(4) N2 N1 C11 C16 165.8(3) N2 C17 C18 C2 13.4(3) N2 C17 C18 C19 -109.8(3) N2 C17 C26 C27 -175.2(3) N2 C17 C26 C31 0.8(5) N3 N4 C39 C38 -1.1(4) N3 N4 C39 C47 175.4(3) N3 C10 C38 C39 20.2(3) N3 C10 C38 C40 -100.9(3) N3 C32 C33 C34 178.9(3) N3 C32 C37 C36 178.8(3) N4 N3 C10 C1 89.0(3) N4 N3 C10 C9 -144.3(3) N4 N3 C10 C38 -23.0(3) N4 N3 C32 C33 156.9(3) N4 N3 C32 C37 -20.3(4) N4 C39 C47 C48 -2.2(5) N4 C39 C47 C52 177.5(3) C1 C2 C3 C4 -141.5(3) C1 C2 C3 C8 42.4(4) C1 C2 C18 C17 97.6(3) C1 C2 C18 C19 -139.9(3) C1 C10 C38 C39 -93.1(3) C1 C10 C38 C40 145.9(3) C2 N1 N2 C17 -12.9(3) C2 N1 C11 C12 -165.8(3) C2 N1 C11 C16 19.0(5) C2 C1 C10 N3 134.7(3) C2 C1 C10 C9 7.0(4) C2 C1 C10 C38 -118.5(3) C2 C3 C4 C5 -174.1(4) C2 C3 C8 C7 173.6(3) C2 C3 C8 C9 -3.5(5) C2 C18 C19 C20 116.1(3) C2 C18 C19 C24 -61.9(4) C3 C2 C18 C17 -141.6(3) C3 C2 C18 C19 -19.1(4) C3 C4 C5 C6 0.1(7) C3 C8 C9 C10 -36.7(5) C4 C3 C8 C7 -2.5(5) C4 C3 C8 C9 -179.6(3) C4 C5 C6 C7 -1.3(7) C5 C6 C7 C8 0.6(6) C6 C7 C8 C3 1.3(5) C6 C7 C8 C9 178.4(3) C7 C8 C9 C10 146.2(3) C8 C3 C4 C5 1.8(6) C8 C9 C10 N3 -91.8(4) C8 C9 C10 C1 33.0(4) C8 C9 C10 C38 155.0(3) C9 C10 C38 C39 142.1(3) C9 C10 C38 C40 21.1(4) C10 N3 N4 C39 16.4(4) C10 N3 C32 C33 -64.3(4) C10 N3 C32 C37 118.5(4) C10 C1 C2 N1 -172.6(3) C10 C1 C2 C3 -43.7(4) C10 C1 C2 C18 78.3(3) C10 C38 C39 N4 -13.2(3) C10 C38 C39 C47 170.3(3) C10 C38 C40 C41 -108.5(4) C10 C38 C40 C45 69.6(4) C11 N1 N2 C17 -164.4(3) C11 N1 C2 C1 56.2(4) C11 N1 C2 C3 -70.5(4) C11 N1 C2 C18 168.2(3) C11 C12 C13 C14 0.3(5) C12 C11 C16 C15 0.0(5) C12 C13 C14 C15 -0.5(5) C13 C14 C15 C16 0.5(6) C14 C15 C16 C11 -0.2(6) C16 C11 C12 C13 -0.1(5) C17 C18 C19 C20 -129.2(3) C17 C18 C19 C24 52.8(4) C17 C26 C27 C28 175.6(3) C17 C26 C31 C30 -175.1(3) C18 C2 C3 C4 100.5(4) C18 C2 C3 C8 -75.5(4) C18 C17 C26 C27 4.3(5) C18 C17 C26 C31 -179.7(3) C18 C19 C20 C21 -175.9(3) C18 C19 C24 C23 174.2(3) C19 C20 C21 C22 2.2(5) C20 C19 C24 C23 -3.9(5) C20 C21 C22 O2 174.2(3) C20 C21 C22 C23 -5.2(5) C21 C22 C23 C24 3.6(5) C22 C23 C24 C19 1.1(6) C24 C19 C20 C21 2.2(5) C25 O2 C22 C21 -171.3(3) C25 O2 C22 C23 8.0(5) C26 C17 C18 C2 -166.1(3) C26 C17 C18 C19 70.6(4) C26 C27 C28 C29 -0.8(6) C27 C26 C31 C30 1.0(5) C27 C28 C29 C30 1.6(6) C28 C29 C30 C31 -1.1(6) C29 C30 C31 C26 -0.2(6) C31 C26 C27 C28 -0.5(5) C32 N3 N4 C39 159.8(3) C32 N3 C10 C1 -51.2(4) C32 N3 C10 C9 75.4(4) C32 N3 C10 C38 -163.3(3) C32 C33 C34 C35 3.8(6) C33 C32 C37 C36 1.6(6) C33 C34 C35 C36 -1.5(6) C34 C35 C36 C37 -0.7(7) C35 C36 C37 C32 0.6(6) C37 C32 C33 C34 -3.8(5) C38 C39 C47 C48 173.9(3) C38 C39 C47 C52 -6.3(5) C38 C40 C41 C42 176.6(3) C38 C40 C45 C44 -177.0(3) C39 C38 C40 C41 136.5(3) C39 C38 C40 C45 -45.4(4) C39 C47 C48 C49 -179.5(3) C39 C47 C52 C51 -179.5(3) C40 C38 C39 N4 109.6(3) C40 C38 C39 C47 -66.9(4) C40 C41 C42 C43 1.0(6) C41 C40 C45 C44 1.2(5) C41 C42 C43 O3 179.4(4) C41 C42 C43 C44 -0.1(6) C42 C43 C44 C45 -0.2(6) C43 C44 C45 C40 -0.4(5) C45 C40 C41 C42 -1.5(6) C46 O3 C43 C42 -174.3(4) C46 O3 C43 C44 5.2(6) C47 C48 C49 C50 -1.5(5) C48 C47 C52 C51 0.3(6) C48 C49 C50 C51 1.2(6) C49 C50 C51 C52 -0.2(6) C50 C51 C52 C47 -0.5(6) C52 C47 C48 C49 0.7(5)