#------------------------------------------------------------------------------ #$Date: 2022-12-16 01:10:35 +0200 (Fri, 16 Dec 2022) $ #$Revision: 279917 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568129.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_1568129 loop_ _publ_author_name 'Kou, Yan' 'Li, Guangwu' 'Han, Yi' 'Li, Mengwei' 'Wang, Tingting' 'Qu, Zhiyu' 'Chen, Yulan' _publ_section_title ; Angularly fused diaza-dinaphthopyrenes: regio-selective synthesis, crystal structures and isomer-dependent mechanochromic fluorescent properties ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D2SC05608A _journal_year 2023 _chemical_formula_moiety 'C44 H44 N2' _chemical_formula_sum 'C44 H44 N2' _chemical_formula_weight 600.81 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc2c5h68 _audit_creation_date 2020-08-22 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2022-06-18 deposited with the CCDC. 2022-12-15 downloaded from the CCDC. ; _cell_angle_alpha 109.684(8) _cell_angle_beta 98.078(7) _cell_angle_gamma 93.683(7) _cell_formula_units_Z 2 _cell_length_a 7.4324(5) _cell_length_b 14.6018(14) _cell_length_c 16.6369(14) _cell_measurement_reflns_used 4454 _cell_measurement_temperature 113.15 _cell_measurement_theta_max 31.7470 _cell_measurement_theta_min 2.2950 _cell_volume 1671.1(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection CrystalClear(Rigaku,2008) _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 113.15 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -115.00 65.00 1.00 12.00 -- -25.00 45.00 0.00 180 2 \w -115.00 65.00 1.00 12.00 -- -25.00 45.00 90.00 180 3 \w -115.00 65.00 1.00 12.00 -- -25.00 45.00 180.00 180 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0015587000 _diffrn_orient_matrix_UB_12 -0.0387861000 _diffrn_orient_matrix_UB_13 0.0166414000 _diffrn_orient_matrix_UB_21 0.0063598000 _diffrn_orient_matrix_UB_22 0.0342744000 _diffrn_orient_matrix_UB_23 0.0425723000 _diffrn_orient_matrix_UB_31 -0.0968667000 _diffrn_orient_matrix_UB_32 -0.0046076000 _diffrn_orient_matrix_UB_33 -0.0048891000 _diffrn_radiation_monochromator confocal _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_unetI/netI 0.1112 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 17814 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 1.609 _diffrn_source 'rotating anode' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)' _exptl_crystal_density_diffrn 1.194 _exptl_crystal_description block _exptl_crystal_F_000 644 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.420 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.080 _refine_ls_extinction_coef 0.009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 420 _refine_ls_number_reflns 6813 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.1649 _refine_ls_R_factor_gt 0.0887 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1204P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2223 _refine_ls_wR_factor_ref 0.2772 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3416 _reflns_number_total 6813 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2sc05608a2.cif _cod_data_source_block r20200810a _cod_database_code 1568129 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C11 H10 N O' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.989 _shelx_estimated_absorpt_t_min 0.986 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, H42 of C42, H41 of C41, H40 of C40, H43 of C43, H24 of C24, H25 of C25, H26 of C26, H28 of C28, H32 of C32, H5 of C5, H4 of C4, H3 of C3, H2 of C2, H18 of C18, H19 of C19 At 1.5 times of: All C(H,H,H) groups, H10 of C10 2. Restrained distances C10-H10 0.95 with sigma of 0.01 3.a Riding coordinates: C10(H10) 3.b Ternary CH refined with riding coordinates: C32(H32) 3.c Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C33(H33A, H33B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B) 3.d Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C24(H24), C25(H25), C26(H26), C28(H28), C40(H40), C41(H41), C42(H42), C43(H43) 3.e Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C34(H34A,H34B,H34C), C38(H38A,H38B, H38C) ; _shelx_res_file ; TITL r20200810a_a.res in P-1 r20200810a.res created by SHELXL-2018/3 at 16:20:42 on 22-Aug-2020 REM Old TITL r20200810a in P-1 REM SHELXT solution in P-1: R1 0.233, Rweak 0.015, Alpha 0.086 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: H43 N2 CELL 0.71073 7.4324 14.6018 16.6369 109.684 98.078 93.683 ZERR 2 0.0005 0.0014 0.0014 0.008 0.007 0.007 LATT 1 SFAC C H N UNIT 88 88 4 DFIX 0.95 0.01 C10 H10 L.S. 4 0 0 PLAN 20 SIZE 0.16 0.18 0.2 TEMP -160 list 4 conf htab bond $h fmap 2 53 acta OMIT -1 3 0 OMIT -7 2 12 OMIT 5 -6 14 REM REM REM WGHT 0.120400 0.258800 EXTI 0.009381 FVAR 0.35878 N1 3 0.458690 0.153726 0.421666 11.00000 0.03384 0.02355 = 0.03143 0.01085 0.00908 -0.00026 N2 3 0.960082 0.620167 0.163133 11.00000 0.03602 0.02977 = 0.03035 0.01243 0.00357 -0.00362 C1 1 0.461593 0.185393 0.510112 11.00000 0.02379 0.02791 = 0.03049 0.01488 0.00602 0.00386 C2 1 0.390913 0.117838 0.544629 11.00000 0.03328 0.02551 = 0.03909 0.01309 0.01079 0.00063 AFIX 43 H2 2 0.341378 0.053539 0.507153 11.00000 -1.20000 AFIX 0 C3 1 0.393120 0.144147 0.631575 11.00000 0.03438 0.03463 = 0.04694 0.02428 0.01447 0.00500 AFIX 43 H3 2 0.343724 0.098278 0.654216 11.00000 -1.20000 AFIX 0 C4 1 0.468162 0.238922 0.688149 11.00000 0.03417 0.03860 = 0.03370 0.01769 0.01035 0.00288 AFIX 43 H4 2 0.468910 0.257362 0.748689 11.00000 -1.20000 AFIX 0 C5 1 0.540124 0.304174 0.654535 11.00000 0.02373 0.03692 = 0.03168 0.01195 0.00463 0.00350 AFIX 43 H5 2 0.593271 0.367477 0.692887 11.00000 -1.20000 AFIX 0 C6 1 0.537622 0.280151 0.564755 11.00000 0.02158 0.02464 = 0.03122 0.01546 0.00563 0.00504 C7 1 0.603702 0.347757 0.525833 11.00000 0.01714 0.02254 = 0.03129 0.01106 0.00406 0.00580 C8 1 0.580239 0.317567 0.433878 11.00000 0.01753 0.02075 = 0.02445 0.00508 0.00498 0.00264 C9 1 0.515304 0.214698 0.385122 11.00000 0.02247 0.02161 = 0.03233 0.01083 0.00419 0.00033 C10 1 0.503755 0.165975 0.287824 11.00000 0.04325 0.02362 = 0.02732 0.00664 0.00954 -0.00731 AFIX 3 H10 2 0.581035 0.204135 0.259604 11.00000 -1.50000 AFIX 0 C11 1 0.573595 0.065255 0.263537 11.00000 0.05181 0.02359 = 0.04093 0.00418 0.01829 -0.00081 AFIX 23 H11A 2 0.503583 0.023258 0.287160 11.00000 -1.20000 H11B 2 0.551470 0.033862 0.199642 11.00000 -1.20000 AFIX 0 C12 1 0.774350 0.071796 0.297520 11.00000 0.05782 0.02781 = 0.08134 0.01620 0.03533 0.00991 AFIX 137 H12A 2 0.844149 0.114449 0.275335 11.00000 -1.50000 H12B 2 0.813757 0.006240 0.278363 11.00000 -1.50000 H12C 2 0.795916 0.098961 0.360998 11.00000 -1.50000 AFIX 0 C13 1 0.302723 0.159607 0.244874 11.00000 0.04392 0.03266 = 0.03672 0.00812 0.00031 -0.00998 AFIX 23 H13A 2 0.230159 0.107225 0.255971 11.00000 -1.20000 H13B 2 0.255908 0.222104 0.274153 11.00000 -1.20000 AFIX 0 C14 1 0.266846 0.139651 0.147995 11.00000 0.05204 0.05374 = 0.04683 0.01584 0.00119 -0.00655 AFIX 23 H14A 2 0.300552 0.074032 0.117121 11.00000 -1.20000 H14B 2 0.345047 0.188652 0.135140 11.00000 -1.20000 AFIX 0 C15 1 0.062891 0.144065 0.114212 11.00000 0.08158 0.08165 = 0.05358 0.01700 -0.00635 -0.00493 AFIX 23 H15A 2 -0.013882 0.090939 0.122275 11.00000 -1.20000 H15B 2 0.026247 0.207249 0.149282 11.00000 -1.20000 AFIX 0 C16 1 0.026591 0.134001 0.019848 11.00000 0.10408 0.08658 = 0.07293 0.02566 -0.00839 0.00510 AFIX 137 H16A 2 0.061560 0.071335 -0.015377 11.00000 -1.50000 H16B 2 0.098569 0.187834 0.011711 11.00000 -1.50000 H16C 2 -0.103919 0.136303 0.001959 11.00000 -1.50000 AFIX 0 C17 1 0.631290 0.388993 0.396245 11.00000 0.01648 0.02244 = 0.02664 0.00724 0.00580 0.00205 C18 1 0.577128 0.378948 0.307575 11.00000 0.02165 0.02048 = 0.03032 0.00751 0.00281 -0.00309 AFIX 43 H18 2 0.487602 0.326356 0.271722 11.00000 -1.20000 AFIX 0 C19 1 0.647924 0.441064 0.272788 11.00000 0.02466 0.02250 = 0.01975 0.00351 0.00391 -0.00028 AFIX 43 H19 2 0.609296 0.429386 0.212920 11.00000 -1.20000 AFIX 0 C20 1 0.779138 0.524020 0.322495 11.00000 0.01851 0.01916 = 0.02643 0.00699 0.00358 0.00059 C21 1 0.800657 0.547730 0.413301 11.00000 0.01579 0.01733 = 0.02346 0.00554 0.00412 0.00387 C22 1 0.730110 0.480957 0.449841 11.00000 0.01647 0.02020 = 0.02467 0.00582 0.00520 0.00441 C23 1 0.758081 0.506942 0.541752 11.00000 0.02049 0.01867 = 0.02260 0.00494 0.00409 0.00395 C24 1 0.691159 0.442166 0.576964 11.00000 0.02149 0.02657 = 0.02371 0.00822 0.00712 0.00459 AFIX 43 H24 2 0.704260 0.461692 0.638231 11.00000 -1.20000 AFIX 0 C25 1 0.852169 0.601949 0.595939 11.00000 0.02502 0.02558 = 0.02329 0.00298 0.00607 0.00247 AFIX 43 H25 2 0.870083 0.619486 0.657159 11.00000 -1.20000 AFIX 0 C26 1 0.914942 0.666102 0.561418 11.00000 0.02655 0.01868 = 0.02357 -0.00040 0.00407 -0.00145 AFIX 43 H26 2 0.974102 0.728626 0.598777 11.00000 -1.20000 AFIX 0 C27 1 0.894359 0.641996 0.468698 11.00000 0.01732 0.01761 = 0.02983 0.00491 0.00474 0.00490 C28 1 0.958570 0.706815 0.432785 11.00000 0.01651 0.01768 = 0.02746 0.00258 -0.00045 -0.00111 AFIX 43 H28 2 1.010252 0.770819 0.470111 11.00000 -1.20000 AFIX 0 C29 1 0.950928 0.682239 0.342683 11.00000 0.01951 0.01875 = 0.02717 0.00676 0.00396 0.00028 C30 1 0.871416 0.586876 0.286103 11.00000 0.02203 0.01657 = 0.02962 0.00742 0.00421 0.00320 C31 1 0.895070 0.558244 0.196346 11.00000 0.02147 0.02536 = 0.03198 0.01211 0.00425 -0.00099 C32 1 0.862048 0.451981 0.132892 11.00000 0.02908 0.02476 = 0.02642 0.00896 0.00736 -0.00324 AFIX 13 H32 2 0.843076 0.408155 0.166740 11.00000 -1.20000 AFIX 0 C33 1 1.028040 0.424507 0.089253 11.00000 0.03500 0.03118 = 0.03168 0.00731 0.00910 -0.00190 AFIX 23 H33A 2 0.997773 0.358080 0.044818 11.00000 -1.20000 H33B 2 1.054208 0.470711 0.059224 11.00000 -1.20000 AFIX 0 C34 1 1.199669 0.425928 0.151934 11.00000 0.03802 0.04922 = 0.03880 0.00583 0.00714 0.00332 AFIX 137 H34A 2 1.299856 0.406364 0.119679 11.00000 -1.50000 H34B 2 1.175374 0.380133 0.181809 11.00000 -1.50000 H34C 2 1.234125 0.492201 0.194615 11.00000 -1.50000 AFIX 0 C35 1 0.690073 0.434865 0.064613 11.00000 0.03127 0.03703 = 0.02538 0.00500 0.00372 -0.00659 AFIX 23 H35A 2 0.718045 0.463567 0.021044 11.00000 -1.20000 H35B 2 0.592911 0.469361 0.092963 11.00000 -1.20000 AFIX 0 C36 1 0.617739 0.325410 0.018019 11.00000 0.03620 0.03962 = 0.03909 -0.00021 0.00217 -0.00549 AFIX 23 H36A 2 0.719912 0.289884 -0.003937 11.00000 -1.20000 H36B 2 0.577005 0.298948 0.060860 11.00000 -1.20000 AFIX 0 C37 1 0.461591 0.304656 -0.056569 11.00000 0.04719 0.04749 = 0.04110 0.00663 0.00285 -0.00300 AFIX 23 H37A 2 0.497328 0.335974 -0.097214 11.00000 -1.20000 H37B 2 0.354190 0.334062 -0.034185 11.00000 -1.20000 AFIX 0 C38 1 0.408351 0.195572 -0.105191 11.00000 0.05305 0.05539 = 0.05445 0.00005 0.00334 -0.01745 AFIX 137 H38A 2 0.304537 0.185557 -0.151869 11.00000 -1.50000 H38B 2 0.373729 0.164124 -0.065133 11.00000 -1.50000 H38C 2 0.512451 0.166685 -0.129928 11.00000 -1.50000 AFIX 0 C39 1 1.014805 0.716721 0.215388 11.00000 0.02557 0.02552 = 0.03132 0.01008 -0.00124 -0.00455 C40 1 1.076866 0.781601 0.175678 11.00000 0.04095 0.03389 = 0.03332 0.01396 0.00052 -0.00715 AFIX 43 H40 2 1.073274 0.758834 0.114765 11.00000 -1.20000 AFIX 0 C41 1 1.141619 0.876281 0.223966 11.00000 0.03567 0.03263 = 0.04622 0.02122 0.00136 -0.00895 AFIX 43 H41 2 1.180035 0.919624 0.196358 11.00000 -1.20000 AFIX 0 C42 1 1.152082 0.910105 0.313011 11.00000 0.03191 0.02209 = 0.04220 0.00969 0.00134 -0.00530 AFIX 43 H42 2 1.200604 0.975983 0.346299 11.00000 -1.20000 AFIX 0 C43 1 1.092579 0.848819 0.353559 11.00000 0.02889 0.02500 = 0.03209 0.00760 0.00481 0.00046 AFIX 43 H43 2 1.099627 0.872996 0.414690 11.00000 -1.20000 AFIX 0 C44 1 1.021311 0.750656 0.305639 11.00000 0.01666 0.02335 = 0.03308 0.01145 0.00352 -0.00022 HKLF 4 REM r20200810a_a.res in P-1 REM wR2 = 0.2772, GooF = S = 1.027, Restrained GooF = 1.032 for all data REM R1 = 0.0887 for 3416 Fo > 4sig(Fo) and 0.1649 for all 6813 data REM 420 parameters refined using 1 restraints END WGHT 0.1204 0.2588 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.420, deepest hole -0.492, 1-sigma level 0.080 Q1 1 0.8680 0.1226 0.2337 11.00000 0.05 0.42 Q2 1 0.8261 0.0793 0.3612 11.00000 0.05 0.42 Q3 1 0.3417 0.0636 0.1401 11.00000 0.05 0.40 Q4 1 0.4115 0.1221 0.1161 11.00000 0.05 0.36 Q5 1 0.4634 0.1113 0.1016 11.00000 0.05 0.36 Q6 1 -0.1843 0.0989 0.1364 11.00000 0.05 0.32 Q7 1 0.4691 0.0351 -0.0004 11.00000 0.05 0.32 Q8 1 0.5488 0.3853 -0.0068 11.00000 0.05 0.31 Q9 1 0.5356 0.2603 0.4020 11.00000 0.05 0.30 Q10 1 -0.1510 0.0854 0.1549 11.00000 0.05 0.29 Q11 1 0.5162 0.2394 0.5444 11.00000 0.05 0.29 Q12 1 0.8967 0.5471 0.3015 11.00000 0.05 0.28 Q13 1 1.1194 0.3247 0.1557 11.00000 0.05 0.28 Q14 1 0.6655 0.4340 0.4231 11.00000 0.05 0.28 Q15 1 0.8962 0.6191 0.4629 11.00000 0.05 0.28 Q16 1 0.5531 0.2839 0.4181 11.00000 0.05 0.28 Q17 1 0.8491 0.5912 0.4432 11.00000 0.05 0.28 Q18 1 0.3297 0.0622 0.6584 11.00000 0.05 0.27 Q19 1 0.3834 0.1240 0.2156 11.00000 0.05 0.27 Q20 1 0.8248 0.5253 0.3531 11.00000 0.05 0.26 ; _shelx_res_checksum 42105 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.721 _oxdiff_exptl_absorpt_empirical_full_min 0.661 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4587(4) 0.1537(2) 0.42167(19) 0.0291(7) Uani 1 1 d . . . . . N2 N 0.9601(4) 0.6202(2) 0.16313(19) 0.0321(7) Uani 1 1 d . . . . . C1 C 0.4616(4) 0.1854(2) 0.5101(2) 0.0260(8) Uani 1 1 d . . . . . C2 C 0.3909(5) 0.1178(3) 0.5446(2) 0.0318(9) Uani 1 1 d . . . . . H2 H 0.341378 0.053539 0.507153 0.038 Uiso 1 1 calc R . . . . C3 C 0.3931(5) 0.1441(3) 0.6316(2) 0.0353(9) Uani 1 1 d . . . . . H3 H 0.343724 0.098278 0.654216 0.042 Uiso 1 1 calc R . . . . C4 C 0.4682(5) 0.2389(3) 0.6881(2) 0.0338(9) Uani 1 1 d . . . . . H4 H 0.468910 0.257362 0.748689 0.041 Uiso 1 1 calc R . . . . C5 C 0.5401(5) 0.3042(3) 0.6545(2) 0.0308(9) Uani 1 1 d . . . . . H5 H 0.593271 0.367477 0.692887 0.037 Uiso 1 1 calc R . . . . C6 C 0.5376(4) 0.2802(2) 0.5648(2) 0.0241(8) Uani 1 1 d . . . . . C7 C 0.6037(4) 0.3478(2) 0.5258(2) 0.0231(8) Uani 1 1 d . . . . . C8 C 0.5802(4) 0.3176(2) 0.4339(2) 0.0215(7) Uani 1 1 d . . . . . C9 C 0.5153(4) 0.2147(2) 0.3851(2) 0.0253(8) Uani 1 1 d . . . . . C10 C 0.5038(5) 0.1660(2) 0.2878(2) 0.0322(9) Uani 1 1 d D . . . . H10 H 0.581035 0.204135 0.259604 0.048 Uiso 1 1 d DR . . . . C11 C 0.5736(5) 0.0653(3) 0.2635(3) 0.0398(10) Uani 1 1 d . . . . . H11A H 0.503583 0.023258 0.287160 0.048 Uiso 1 1 calc R . . . . H11B H 0.551470 0.033862 0.199642 0.048 Uiso 1 1 calc R . . . . C12 C 0.7743(6) 0.0718(3) 0.2975(3) 0.0538(13) Uani 1 1 d . . . . . H12A H 0.844149 0.114449 0.275335 0.081 Uiso 1 1 calc GR . . . . H12B H 0.813757 0.006240 0.278363 0.081 Uiso 1 1 calc GR . . . . H12C H 0.795916 0.098961 0.360998 0.081 Uiso 1 1 calc GR . . . . C13 C 0.3027(5) 0.1596(3) 0.2449(2) 0.0402(10) Uani 1 1 d . . . . . H13A H 0.230159 0.107225 0.255971 0.048 Uiso 1 1 calc R . . . . H13B H 0.255908 0.222104 0.274153 0.048 Uiso 1 1 calc R . . . . C14 C 0.2668(6) 0.1397(3) 0.1480(3) 0.0527(12) Uani 1 1 d . . . . . H14A H 0.300552 0.074032 0.117121 0.063 Uiso 1 1 calc R . . . . H14B H 0.345047 0.188652 0.135140 0.063 Uiso 1 1 calc R . . . . C15 C 0.0629(7) 0.1441(4) 0.1142(3) 0.0765(16) Uani 1 1 d . . . . . H15A H -0.013882 0.090939 0.122275 0.092 Uiso 1 1 calc R . . . . H15B H 0.026247 0.207249 0.149282 0.092 Uiso 1 1 calc R . . . . C16 C 0.0266(8) 0.1340(4) 0.0198(4) 0.0912(19) Uani 1 1 d . . . . . H16A H 0.061560 0.071335 -0.015377 0.137 Uiso 1 1 calc GR . . . . H16B H 0.098569 0.187834 0.011711 0.137 Uiso 1 1 calc GR . . . . H16C H -0.103919 0.136303 0.001959 0.137 Uiso 1 1 calc GR . . . . C17 C 0.6313(4) 0.3890(2) 0.3962(2) 0.0220(7) Uani 1 1 d . . . . . C18 C 0.5771(4) 0.3789(2) 0.3076(2) 0.0249(8) Uani 1 1 d . . . . . H18 H 0.487602 0.326356 0.271722 0.030 Uiso 1 1 calc R . . . . C19 C 0.6479(4) 0.4411(2) 0.2728(2) 0.0234(8) Uani 1 1 d . . . . . H19 H 0.609296 0.429386 0.212920 0.028 Uiso 1 1 calc R . . . . C20 C 0.7791(4) 0.5240(2) 0.3225(2) 0.0217(7) Uani 1 1 d . . . . . C21 C 0.8007(4) 0.5477(2) 0.4133(2) 0.0191(7) Uani 1 1 d . . . . . C22 C 0.7301(4) 0.4810(2) 0.4498(2) 0.0207(7) Uani 1 1 d . . . . . C23 C 0.7581(4) 0.5069(2) 0.5418(2) 0.0211(7) Uani 1 1 d . . . . . C24 C 0.6912(4) 0.4422(2) 0.5770(2) 0.0237(8) Uani 1 1 d . . . . . H24 H 0.704260 0.461692 0.638231 0.028 Uiso 1 1 calc R . . . . C25 C 0.8522(4) 0.6019(2) 0.5959(2) 0.0259(8) Uani 1 1 d . . . . . H25 H 0.870083 0.619486 0.657159 0.031 Uiso 1 1 calc R . . . . C26 C 0.9149(4) 0.6661(2) 0.5614(2) 0.0252(8) Uani 1 1 d . . . . . H26 H 0.974102 0.728626 0.598777 0.030 Uiso 1 1 calc R . . . . C27 C 0.8944(4) 0.6420(2) 0.4687(2) 0.0223(8) Uani 1 1 d . . . . . C28 C 0.9586(4) 0.7068(2) 0.4328(2) 0.0225(8) Uani 1 1 d . . . . . H28 H 1.010252 0.770819 0.470111 0.027 Uiso 1 1 calc R . . . . C29 C 0.9509(4) 0.6822(2) 0.3427(2) 0.0222(8) Uani 1 1 d . . . . . C30 C 0.8714(4) 0.5869(2) 0.2861(2) 0.0229(8) Uani 1 1 d . . . . . C31 C 0.8951(4) 0.5582(2) 0.1963(2) 0.0259(8) Uani 1 1 d . . . . . C32 C 0.8620(5) 0.4520(2) 0.1329(2) 0.0268(8) Uani 1 1 d . . . . . H32 H 0.843076 0.408155 0.166740 0.032 Uiso 1 1 calc R . . . . C33 C 1.0280(5) 0.4245(3) 0.0893(2) 0.0335(9) Uani 1 1 d . . . . . H33A H 0.997773 0.358080 0.044818 0.040 Uiso 1 1 calc R . . . . H33B H 1.054208 0.470711 0.059224 0.040 Uiso 1 1 calc R . . . . C34 C 1.1997(5) 0.4259(3) 0.1519(3) 0.0445(11) Uani 1 1 d . . . . . H34A H 1.299856 0.406364 0.119679 0.067 Uiso 1 1 calc GR . . . . H34B H 1.175374 0.380133 0.181809 0.067 Uiso 1 1 calc GR . . . . H34C H 1.234125 0.492201 0.194615 0.067 Uiso 1 1 calc GR . . . . C35 C 0.6901(5) 0.4349(3) 0.0646(2) 0.0334(9) Uani 1 1 d . . . . . H35A H 0.718045 0.463567 0.021044 0.040 Uiso 1 1 calc R . . . . H35B H 0.592911 0.469361 0.092963 0.040 Uiso 1 1 calc R . . . . C36 C 0.6177(5) 0.3254(3) 0.0180(2) 0.0428(11) Uani 1 1 d . . . . . H36A H 0.719912 0.289884 -0.003937 0.051 Uiso 1 1 calc R . . . . H36B H 0.577005 0.298948 0.060860 0.051 Uiso 1 1 calc R . . . . C37 C 0.4616(6) 0.3047(3) -0.0566(3) 0.0485(11) Uani 1 1 d . . . . . H37A H 0.497328 0.335974 -0.097214 0.058 Uiso 1 1 calc R . . . . H37B H 0.354190 0.334062 -0.034185 0.058 Uiso 1 1 calc R . . . . C38 C 0.4084(6) 0.1956(3) -0.1052(3) 0.0610(14) Uani 1 1 d . . . . . H38A H 0.304537 0.185557 -0.151869 0.091 Uiso 1 1 calc GR . . . . H38B H 0.373729 0.164124 -0.065133 0.091 Uiso 1 1 calc GR . . . . H38C H 0.512451 0.166685 -0.129928 0.091 Uiso 1 1 calc GR . . . . C39 C 1.0148(5) 0.7167(2) 0.2154(2) 0.0284(8) Uani 1 1 d . . . . . C40 C 1.0769(5) 0.7816(3) 0.1757(2) 0.0366(9) Uani 1 1 d . . . . . H40 H 1.073274 0.758834 0.114765 0.044 Uiso 1 1 calc R . . . . C41 C 1.1416(5) 0.8763(3) 0.2240(3) 0.0374(10) Uani 1 1 d . . . . . H41 H 1.180035 0.919624 0.196358 0.045 Uiso 1 1 calc R . . . . C42 C 1.1521(5) 0.9101(3) 0.3130(2) 0.0334(9) Uani 1 1 d . . . . . H42 H 1.200604 0.975983 0.346299 0.040 Uiso 1 1 calc R . . . . C43 C 1.0926(5) 0.8488(2) 0.3536(2) 0.0295(8) Uani 1 1 d . . . . . H43 H 1.099627 0.872996 0.414690 0.035 Uiso 1 1 calc R . . . . C44 C 1.0213(4) 0.7507(2) 0.3056(2) 0.0242(8) Uani 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 N1 0.0338(17) 0.0235(15) 0.0314(17) 0.0108(13) 0.0091(14) -0.0003(13) N2 0.0360(18) 0.0298(17) 0.0303(17) 0.0124(14) 0.0036(14) -0.0036(14) C1 0.0238(18) 0.0279(19) 0.030(2) 0.0149(16) 0.0060(16) 0.0039(15) C2 0.033(2) 0.0255(19) 0.039(2) 0.0131(17) 0.0108(18) 0.0006(16) C3 0.034(2) 0.035(2) 0.047(3) 0.0243(19) 0.0145(19) 0.0050(17) C4 0.034(2) 0.039(2) 0.034(2) 0.0177(18) 0.0103(18) 0.0029(18) C5 0.0237(19) 0.037(2) 0.032(2) 0.0120(17) 0.0046(16) 0.0035(16) C6 0.0216(18) 0.0246(18) 0.031(2) 0.0155(16) 0.0056(15) 0.0050(14) C7 0.0171(17) 0.0225(17) 0.031(2) 0.0111(15) 0.0041(15) 0.0058(14) C8 0.0175(17) 0.0207(17) 0.0244(19) 0.0051(14) 0.0050(14) 0.0026(14) C9 0.0225(18) 0.0216(17) 0.032(2) 0.0108(15) 0.0042(15) 0.0003(14) C10 0.043(2) 0.0236(18) 0.027(2) 0.0066(16) 0.0095(17) -0.0073(16) C11 0.052(3) 0.0236(19) 0.041(2) 0.0042(17) 0.018(2) -0.0008(18) C12 0.058(3) 0.028(2) 0.081(3) 0.016(2) 0.035(3) 0.010(2) C13 0.044(2) 0.033(2) 0.037(2) 0.0081(18) 0.0003(19) -0.0100(18) C14 0.052(3) 0.054(3) 0.047(3) 0.016(2) 0.001(2) -0.007(2) C15 0.082(4) 0.082(4) 0.054(3) 0.017(3) -0.006(3) -0.005(3) C16 0.104(5) 0.087(4) 0.073(4) 0.026(3) -0.008(3) 0.005(4) C17 0.0165(16) 0.0224(17) 0.0266(19) 0.0072(15) 0.0058(14) 0.0020(14) C18 0.0216(18) 0.0205(17) 0.030(2) 0.0075(15) 0.0028(15) -0.0031(14) C19 0.0247(18) 0.0225(17) 0.0198(18) 0.0035(14) 0.0039(15) -0.0003(14) C20 0.0185(17) 0.0192(17) 0.0264(19) 0.0070(14) 0.0036(15) 0.0006(13) C21 0.0158(16) 0.0173(16) 0.0235(18) 0.0055(14) 0.0041(14) 0.0039(13) C22 0.0165(17) 0.0202(17) 0.0247(18) 0.0058(14) 0.0052(14) 0.0044(13) C23 0.0205(17) 0.0187(16) 0.0226(18) 0.0049(14) 0.0041(14) 0.0039(14) C24 0.0215(18) 0.0266(18) 0.0237(19) 0.0082(15) 0.0071(15) 0.0046(14) C25 0.0250(18) 0.0256(18) 0.0233(18) 0.0030(15) 0.0061(15) 0.0025(15) C26 0.0265(19) 0.0187(17) 0.0236(19) -0.0004(14) 0.0041(15) -0.0014(14) C27 0.0173(17) 0.0176(16) 0.030(2) 0.0049(14) 0.0047(15) 0.0049(13) C28 0.0165(17) 0.0177(16) 0.0275(19) 0.0026(14) -0.0005(14) -0.0011(13) C29 0.0195(17) 0.0188(16) 0.0272(19) 0.0068(14) 0.0040(15) 0.0003(14) C30 0.0220(18) 0.0166(16) 0.0296(19) 0.0074(14) 0.0042(15) 0.0032(14) C31 0.0215(18) 0.0254(18) 0.032(2) 0.0121(16) 0.0043(15) -0.0010(15) C32 0.0291(19) 0.0248(18) 0.0264(19) 0.0090(15) 0.0074(16) -0.0032(15) C33 0.035(2) 0.031(2) 0.032(2) 0.0073(17) 0.0091(17) -0.0019(17) C34 0.038(2) 0.049(3) 0.039(2) 0.006(2) 0.0071(19) 0.003(2) C35 0.031(2) 0.037(2) 0.025(2) 0.0050(17) 0.0037(16) -0.0066(17) C36 0.036(2) 0.040(2) 0.039(2) -0.0002(19) 0.0022(19) -0.0055(18) C37 0.047(3) 0.047(3) 0.041(3) 0.007(2) 0.003(2) -0.003(2) C38 0.053(3) 0.055(3) 0.054(3) 0.000(2) 0.003(2) -0.017(2) C39 0.0256(19) 0.0255(19) 0.031(2) 0.0101(16) -0.0012(16) -0.0045(15) C40 0.041(2) 0.034(2) 0.033(2) 0.0140(18) 0.0005(18) -0.0071(18) C41 0.036(2) 0.033(2) 0.046(3) 0.0212(19) 0.0014(19) -0.0090(17) C42 0.032(2) 0.0221(18) 0.042(2) 0.0097(17) 0.0013(18) -0.0053(16) C43 0.029(2) 0.0250(18) 0.032(2) 0.0076(16) 0.0048(16) 0.0005(15) C44 0.0167(17) 0.0234(18) 0.033(2) 0.0115(15) 0.0035(15) -0.0002(14) 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' 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 C9 N1 C1 120.4(3) . . ? C31 N2 C39 119.6(3) . . ? N1 C1 C2 117.6(3) . . ? N1 C1 C6 121.9(3) . . ? C6 C1 C2 120.5(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.8 . . ? C2 C3 H3 119.8 . . ? C2 C3 C4 120.5(3) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 120.5 . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4 120.5 . . ? C4 C5 H5 119.0 . . ? C4 C5 C6 122.1(3) . . ? C6 C5 H5 119.0 . . ? C1 C6 C5 117.5(3) . . ? C1 C6 C7 118.3(3) . . ? C5 C6 C7 124.1(3) . . ? C8 C7 C6 119.0(3) . . ? C24 C7 C6 121.4(3) . . ? C24 C7 C8 119.6(3) . . ? C7 C8 C9 116.9(3) . . ? C7 C8 C17 118.0(3) . . ? C17 C8 C9 125.0(3) . . ? N1 C9 C8 122.8(3) . . ? N1 C9 C10 112.6(3) . . ? C8 C9 C10 124.7(3) . . ? C9 C10 H10 114.8 . . ? C9 C10 C11 112.3(3) . . ? C9 C10 C13 107.6(3) . . ? C11 C10 H10 104.1 . . ? C11 C10 C13 112.0(3) . . ? C13 C10 H10 105.9 . . ? C10 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C12 C11 C10 112.4(3) . . ? C12 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 108.1 . . ? C10 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C14 C13 C10 116.9(3) . . ? C14 C13 H13A 108.1 . . ? C14 C13 H13B 108.1 . . ? C13 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C13 C14 C15 111.9(4) . . ? H14A C14 H14B 107.9 . . ? C15 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? C14 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C16 C15 C14 113.1(5) . . ? C16 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C8 124.9(3) . . ? C22 C17 C8 120.0(3) . . ? C22 C17 C18 114.8(3) . . ? C17 C18 H18 118.7 . . ? C19 C18 C17 122.6(3) . . ? C19 C18 H18 118.7 . . ? C18 C19 H19 118.7 . . ? C18 C19 C20 122.6(3) . . ? C20 C19 H19 118.7 . . ? C19 C20 C30 124.2(3) . . ? C21 C20 C19 114.9(3) . . ? C21 C20 C30 120.6(3) . . ? C20 C21 C22 121.2(3) . . ? C20 C21 C27 118.6(3) . . ? C22 C21 C27 120.2(3) . . ? C17 C22 C23 119.6(3) . . ? C21 C22 C17 121.0(3) . . ? C21 C22 C23 119.4(3) . . ? C22 C23 C25 119.3(3) . . ? C24 C23 C22 119.4(3) . . ? C24 C23 C25 121.2(3) . . ? C7 C24 H24 118.7 . . ? C23 C24 C7 122.6(3) . . ? C23 C24 H24 118.7 . . ? C23 C25 H25 119.4 . . ? C26 C25 C23 121.2(3) . . ? C26 C25 H25 119.4 . . ? C25 C26 H26 119.3 . . ? C25 C26 C27 121.4(3) . . ? C27 C26 H26 119.3 . . ? C21 C27 C26 118.4(3) . . ? C28 C27 C21 119.7(3) . . ? C28 C27 C26 121.9(3) . . ? C27 C28 H28 118.7 . . ? C27 C28 C29 122.7(3) . . ? C29 C28 H28 118.7 . . ? C28 C29 C30 119.1(3) . . ? C28 C29 C44 122.2(3) . . ? C30 C29 C44 118.7(3) . . ? C20 C30 C31 124.4(3) . . ? C29 C30 C20 118.1(3) . . ? C29 C30 C31 117.4(3) . . ? N2 C31 C30 122.8(3) . . ? N2 C31 C32 113.2(3) . . ? C30 C31 C32 123.8(3) . . ? C31 C32 H32 108.0 . . ? C33 C32 C31 111.0(3) . . ? C33 C32 H32 108.0 . . ? C33 C32 C35 110.4(3) . . ? C35 C32 C31 111.4(3) . . ? C35 C32 H32 108.0 . . ? C32 C33 H33A 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C34 C33 C32 113.7(3) . . ? C34 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.0 . . ? C32 C35 H35B 109.0 . . ? C32 C35 C36 113.0(3) . . ? H35A C35 H35B 107.8 . . ? C36 C35 H35A 109.0 . . ? C36 C35 H35B 109.0 . . ? C35 C36 H36A 108.6 . . ? C35 C36 H36B 108.6 . . ? H36A C36 H36B 107.6 . . ? C37 C36 C35 114.7(3) . . ? C37 C36 H36A 108.6 . . ? C37 C36 H36B 108.6 . . ? C36 C37 H37A 109.1 . . ? C36 C37 H37B 109.1 . . ? C36 C37 C38 112.3(4) . . ? H37A C37 H37B 107.9 . . ? C38 C37 H37A 109.1 . . ? C38 C37 H37B 109.1 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38B 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N2 C39 C40 117.4(3) . . ? N2 C39 C44 122.9(3) . . ? C44 C39 C40 119.5(3) . . ? C39 C40 H40 119.8 . . ? C41 C40 C39 120.5(4) . . ? C41 C40 H40 119.8 . . ? C40 C41 H41 119.7 . . ? C40 C41 C42 120.6(4) . . ? C42 C41 H41 119.7 . . ? C41 C42 H42 119.8 . . ? C43 C42 C41 120.3(3) . . ? C43 C42 H42 119.8 . . ? C42 C43 H43 119.6 . . ? C42 C43 C44 120.9(3) . . ? C44 C43 H43 119.6 . . ? C39 C44 C29 117.3(3) . . ? C39 C44 C43 118.2(3) . . ? C43 C44 C29 124.5(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.382(4) . ? N1 C9 1.314(4) . ? N2 C31 1.308(4) . ? N2 C39 1.382(4) . ? C1 C2 1.407(4) . ? C1 C6 1.403(5) . ? C2 H2 0.9500 . ? C2 C3 1.363(5) . ? C3 H3 0.9500 . ? C3 C4 1.410(5) . ? C4 H4 0.9500 . ? C4 C5 1.373(5) . ? C5 H5 0.9500 . ? C5 C6 1.412(5) . ? C6 C7 1.447(4) . ? C7 C8 1.423(4) . ? C7 C24 1.409(5) . ? C8 C9 1.457(4) . ? C8 C17 1.442(4) . ? C9 C10 1.520(5) . ? C10 H10 1.0352 . ? C10 C11 1.534(5) . ? C10 C13 1.546(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.504(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.519(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.554(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.510(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.428(4) . ? C17 C22 1.421(4) . ? C18 H18 0.9500 . ? C18 C19 1.346(4) . ? C19 H19 0.9500 . ? C19 C20 1.431(4) . ? C20 C21 1.414(4) . ? C20 C30 1.446(4) . ? C21 C22 1.421(4) . ? C21 C27 1.439(4) . ? C22 C23 1.427(4) . ? C23 C24 1.371(4) . ? C23 C25 1.443(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C25 C26 1.344(4) . ? C26 H26 0.9500 . ? C26 C27 1.445(4) . ? C27 C28 1.372(4) . ? C28 H28 0.9500 . ? C28 C29 1.411(4) . ? C29 C30 1.425(4) . ? C29 C44 1.446(4) . ? C30 C31 1.449(5) . ? C31 C32 1.535(4) . ? C32 H32 1.0000 . ? C32 C33 1.526(5) . ? C32 C35 1.532(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33 C34 1.524(5) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C35 C36 1.543(5) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C36 C37 1.508(5) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C37 C38 1.520(6) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.413(5) . ? C39 C44 1.406(5) . ? C40 H40 0.9500 . ? C40 C41 1.359(5) . ? C41 H41 0.9500 . ? C41 C42 1.384(5) . ? C42 H42 0.9500 . ? C42 C43 1.375(5) . ? C43 H43 0.9500 . ? C43 C44 1.409(5) . ? 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 178.8(3) . . . . ? N1 C1 C6 C5 -177.7(3) . . . . ? N1 C1 C6 C7 4.0(5) . . . . ? N1 C9 C10 C11 -43.9(4) . . . . ? N1 C9 C10 C13 79.8(4) . . . . ? N2 C31 C32 C33 47.9(4) . . . . ? N2 C31 C32 C35 -75.4(4) . . . . ? N2 C39 C40 C41 -176.6(3) . . . . ? N2 C39 C44 C29 -5.9(5) . . . . ? N2 C39 C44 C43 175.2(3) . . . . ? C1 N1 C9 C8 -1.1(5) . . . . ? C1 N1 C9 C10 179.3(3) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C1 C6 C7 C8 3.4(5) . . . . ? C1 C6 C7 C24 -176.3(3) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? C2 C1 C6 C7 -178.3(3) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? C4 C5 C6 C7 176.9(3) . . . . ? C5 C6 C7 C8 -174.9(3) . . . . ? C5 C6 C7 C24 5.5(5) . . . . ? C6 C1 C2 C3 0.9(5) . . . . ? C6 C7 C8 C9 -9.0(4) . . . . ? C6 C7 C8 C17 174.3(3) . . . . ? C6 C7 C24 C23 178.7(3) . . . . ? C7 C8 C9 N1 8.2(5) . . . . ? C7 C8 C9 C10 -172.2(3) . . . . ? C7 C8 C17 C18 -164.0(3) . . . . ? C7 C8 C17 C22 10.4(4) . . . . ? C8 C7 C24 C23 -0.9(5) . . . . ? C8 C9 C10 C11 136.5(3) . . . . ? C8 C9 C10 C13 -99.8(4) . . . . ? C8 C17 C18 C19 -170.8(3) . . . . ? C8 C17 C22 C21 172.5(3) . . . . ? C8 C17 C22 C23 -7.9(4) . . . . ? C9 N1 C1 C2 177.0(3) . . . . ? C9 N1 C1 C6 -5.2(5) . . . . ? C9 C8 C17 C18 19.5(5) . . . . ? C9 C8 C17 C22 -166.0(3) . . . . ? C9 C10 C11 C12 -64.6(4) . . . . ? C9 C10 C13 C14 163.7(3) . . . . ? C10 C13 C14 C15 -175.0(4) . . . . ? C11 C10 C13 C14 -72.3(4) . . . . ? C13 C10 C11 C12 174.2(3) . . . . ? C13 C14 C15 C16 174.6(4) . . . . ? C17 C8 C9 N1 -175.3(3) . . . . ? C17 C8 C9 C10 4.3(5) . . . . ? C17 C18 C19 C20 -2.0(5) . . . . ? C17 C22 C23 C24 0.8(4) . . . . ? C17 C22 C23 C25 -177.6(3) . . . . ? C18 C17 C22 C21 -12.6(4) . . . . ? C18 C17 C22 C23 167.1(3) . . . . ? C18 C19 C20 C21 -12.5(4) . . . . ? C18 C19 C20 C30 173.8(3) . . . . ? C19 C20 C21 C22 14.1(4) . . . . ? C19 C20 C21 C27 -165.3(3) . . . . ? C19 C20 C30 C29 160.1(3) . . . . ? C19 C20 C30 C31 -22.4(5) . . . . ? C20 C21 C22 C17 -1.6(5) . . . . ? C20 C21 C22 C23 178.7(3) . . . . ? C20 C21 C27 C26 179.6(3) . . . . ? C20 C21 C27 C28 0.7(4) . . . . ? C20 C30 C31 N2 171.8(3) . . . . ? C20 C30 C31 C32 -13.4(5) . . . . ? C21 C20 C30 C29 -13.3(4) . . . . ? C21 C20 C30 C31 164.2(3) . . . . ? C21 C22 C23 C24 -179.5(3) . . . . ? C21 C22 C23 C25 2.1(4) . . . . ? C21 C27 C28 C29 -5.6(5) . . . . ? C22 C17 C18 C19 14.5(5) . . . . ? C22 C21 C27 C26 0.3(4) . . . . ? C22 C21 C27 C28 -178.6(3) . . . . ? C22 C23 C24 C7 3.6(5) . . . . ? C22 C23 C25 C26 -0.4(5) . . . . ? C23 C25 C26 C27 -1.3(5) . . . . ? C24 C7 C8 C9 170.7(3) . . . . ? C24 C7 C8 C17 -6.1(4) . . . . ? C24 C23 C25 C26 -178.8(3) . . . . ? C25 C23 C24 C7 -178.0(3) . . . . ? C25 C26 C27 C21 1.4(5) . . . . ? C25 C26 C27 C28 -179.7(3) . . . . ? C26 C27 C28 C29 175.6(3) . . . . ? C27 C21 C22 C17 177.7(3) . . . . ? C27 C21 C22 C23 -2.0(4) . . . . ? C27 C28 C29 C30 0.8(5) . . . . ? C27 C28 C29 C44 -179.1(3) . . . . ? C28 C29 C30 C20 8.4(4) . . . . ? C28 C29 C30 C31 -169.2(3) . . . . ? C28 C29 C44 C39 176.9(3) . . . . ? C28 C29 C44 C43 -4.2(5) . . . . ? C29 C30 C31 N2 -10.7(5) . . . . ? C29 C30 C31 C32 164.1(3) . . . . ? C30 C20 C21 C22 -172.0(3) . . . . ? C30 C20 C21 C27 8.7(4) . . . . ? C30 C29 C44 C39 -3.1(5) . . . . ? C30 C29 C44 C43 175.8(3) . . . . ? C30 C31 C32 C33 -127.3(3) . . . . ? C30 C31 C32 C35 109.3(4) . . . . ? C31 N2 C39 C40 -177.4(3) . . . . ? C31 N2 C39 C44 6.5(5) . . . . ? C31 C32 C33 C34 64.0(4) . . . . ? C31 C32 C35 C36 -162.2(3) . . . . ? C32 C35 C36 C37 -173.4(3) . . . . ? C33 C32 C35 C36 74.1(4) . . . . ? C35 C32 C33 C34 -172.0(3) . . . . ? C35 C36 C37 C38 174.5(4) . . . . ? C39 N2 C31 C30 2.1(5) . . . . ? C39 N2 C31 C32 -173.2(3) . . . . ? C39 C40 C41 C42 1.6(6) . . . . ? C40 C39 C44 C29 178.1(3) . . . . ? C40 C39 C44 C43 -0.8(5) . . . . ? C40 C41 C42 C43 -1.7(6) . . . . ? C41 C42 C43 C44 0.5(5) . . . . ? C42 C43 C44 C29 -178.1(3) . . . . ? C42 C43 C44 C39 0.8(5) . . . . ? C44 C29 C30 C20 -171.6(3) . . . . ? C44 C29 C30 C31 10.8(4) . . . . ? C44 C39 C40 C41 -0.3(5) . . . . ?