data_import _publ_requested_journal 'J. Org. Chem' _publ_contact_author_name 'Miguel A. Garcia-Garibay' _publ_contact_author_address ; Chemistry and Biochemistry Department University of California Los Angeles Charles E. Young Drive East Los Angeles, CA 90095 USA ; _publ_contact_author_email 'mgg@chem.ucla.edu' _publ_contact_author_phone '310 825 3159' _publ_contact_author_fax '' loop_ _publ_author_name _publ_author_address 'Santillan, Rosa' ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; "Rodr\'iguez-Molina, Braulio" ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; 'Farf\'an, Norberto' ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; "Garcia-Garibay, Miguel" ; Chemistry and Biochemistry Department University of California Los Angeles Charles E. Young Drive East Los Angeles, CA 90095 USA ; _publ_section_title ; "Synthesis, Characterization and Rotational Dynamics of Crystalline Molecular Compasses With N-Heterocyclic Rotators" ; _audit_creation_date 2009-05-17T22:24:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _chemical_name_common ? _chemical_name_systematic ; 3,6-Bis(3,3,3-triphenylpropynyl)pyridazine ; _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 N2' _chemical_formula_sum 'C46 H32 N2' _chemical_formula_weight 612.74 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 9.01140(10) _cell_length_b 15.1195(2) _cell_length_c 24.9752(5) _cell_angle_alpha 90 _cell_angle_beta 95.0690(10) _cell_angle_gamma 90 _cell_volume 3389.51(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6980 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 293(2) _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enraf Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.934478E-1 _diffrn_orient_matrix_ub_12 0.358347E-1 _diffrn_orient_matrix_ub_13 -0.51203E-2 _diffrn_orient_matrix_ub_21 0.218217E-1 _diffrn_orient_matrix_ub_22 0.138013E-1 _diffrn_orient_matrix_ub_23 -0.376692E-1 _diffrn_orient_matrix_ub_31 -0.565921E-1 _diffrn_orient_matrix_ub_32 -0.538504E-1 _diffrn_orient_matrix_ub_33 -0.130616E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_unetI/netI 0.0862 _diffrn_reflns_number 13797 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 7604 _reflns_number_gt 3750 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0744P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0076(11) _refine_ls_number_reflns 7604 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1403 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.152 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.23 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.033 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 0 '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_ _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0766(2) 0.99461(12) 0.11255(7) 0.0473(5) Uani 1 1 d . . . H1 H 1.1581 1.0224 0.0995 0.057 Uiso 1 1 calc R . . C2 C 0.9329(2) 1.02609(11) 0.10016(7) 0.0431(5) Uani 1 1 d . . . C3 C 0.9011(2) 1.10185(13) 0.06633(8) 0.0508(5) Uani 1 1 d . . . C4 C 0.8709(2) 1.16418(12) 0.03810(7) 0.0474(5) Uani 1 1 d . . . C5 C 0.8314(2) 1.24324(12) 0.00468(7) 0.0443(3) Uani 1 1 d . . . C6 C 0.97671(19) 1.28117(12) -0.01436(7) 0.0439(5) Uani 1 1 d . . . C7 C 1.0725(2) 1.22684(14) -0.03931(8) 0.0551(5) Uani 1 1 d . . . H7 H 1.0505 1.1669 -0.0426 0.066 Uiso 1 1 calc R . . C8 C 1.1996(2) 1.25841(17) -0.05954(8) 0.0628(6) Uani 1 1 d . . . H8 H 1.2613 1.2198 -0.0763 0.075 Uiso 1 1 calc R . . C9 C 1.2352(3) 1.34491(18) -0.05521(11) 0.0762(7) Uani 1 1 d . . . H9 H 1.3211 1.3663 -0.0688 0.091 Uiso 1 1 calc R . . C10 C 1.1443(3) 1.39991(17) -0.03089(13) 0.1031(10) Uani 1 1 d . . . H10 H 1.1681 1.4597 -0.0278 0.124 Uiso 1 1 calc R . . C11 C 1.0161(3) 1.36896(14) -0.01040(11) 0.0796(7) Uani 1 1 d . . . H11 H 0.9555 1.4083 0.0063 0.095 Uiso 1 1 calc R . . C12 C 0.7529(2) 1.30869(12) 0.04038(7) 0.0458(5) Uani 1 1 d . . . C13 C 0.8222(3) 1.33313(16) 0.08957(9) 0.0803(8) Uani 1 1 d . . . H13 H 0.9151 1.3095 0.1007 0.096 Uiso 1 1 calc R . . C14 C 0.7573(4) 1.39149(18) 0.12247(10) 0.0967(9) Uani 1 1 d . . . H14 H 0.8069 1.4069 0.1554 0.116 Uiso 1 1 calc R . . C15 C 0.6220(3) 1.42687(18) 0.10756(11) 0.0850(8) Uani 1 1 d . . . H15 H 0.5779 1.4663 0.13 0.102 Uiso 1 1 calc R . . C16 C 0.5521(3) 1.4039(2) 0.05956(13) 0.1013(10) Uani 1 1 d . . . H16 H 0.459 1.4277 0.0489 0.122 Uiso 1 1 calc R . . C17 C 0.6176(2) 1.34510(16) 0.02576(10) 0.0787(7) Uani 1 1 d . . . H17 H 0.568 1.3305 -0.0073 0.094 Uiso 1 1 calc R . . C18 C 0.72687(19) 1.21637(12) -0.04510(7) 0.0431(5) Uani 1 1 d . . . C19 C 0.6432(2) 1.13972(13) -0.04679(8) 0.0534(5) Uani 1 1 d . . . H19 H 0.6544 1.1001 -0.0182 0.064 Uiso 1 1 calc R . . C20 C 0.5427(2) 1.12114(16) -0.09074(9) 0.0663(6) Uani 1 1 d . . . H20 H 0.487 1.0693 -0.0913 0.08 Uiso 1 1 calc R . . C21 C 0.5250(2) 1.17847(18) -0.13320(9) 0.0710(7) Uani 1 1 d . . . H21 H 0.4565 1.1663 -0.1623 0.085 Uiso 1 1 calc R . . C22 C 0.6086(3) 1.25367(18) -0.13239(9) 0.0736(7) Uani 1 1 d . . . H22 H 0.5982 1.2926 -0.1613 0.088 Uiso 1 1 calc R . . C23 C 0.7090(2) 1.27240(14) -0.08869(8) 0.0609(6) Uani 1 1 d . . . H23 H 0.7655 1.3239 -0.0888 0.073 Uiso 1 1 calc R . . C24 C 1.0945(2) 0.92170(12) 0.14446(7) 0.0443(5) Uani 1 1 d . . . H24 H 1.1884 0.8978 0.1535 0.053 Uiso 1 1 calc R . . C25 C 0.96824(19) 0.88418(11) 0.16305(7) 0.0397(4) Uani 1 1 d . . . C26 C 0.9734(2) 0.80679(12) 0.19630(7) 0.0443(3) Uani 1 1 d . . . C27 C 0.97162(19) 0.74096(12) 0.22262(7) 0.0433(4) Uani 1 1 d . . . C28 C 0.95642(18) 0.65794(11) 0.25314(7) 0.0404(4) Uani 1 1 d . . . C29 C 0.78732(19) 0.63973(12) 0.25342(7) 0.0435(5) Uani 1 1 d . . . C30 C 0.6972(2) 0.70581(14) 0.27082(9) 0.0642(6) Uani 1 1 d . . . H30 H 0.7385 0.7606 0.2803 0.077 Uiso 1 1 calc R . . C31 C 0.5469(2) 0.69187(17) 0.27437(10) 0.0762(7) Uani 1 1 d . . . H31 H 0.4887 0.7368 0.2869 0.091 Uiso 1 1 calc R . . C32 C 0.4834(2) 0.61290(18) 0.25963(9) 0.0693(6) Uani 1 1 d . . . H32 H 0.3821 0.6037 0.2619 0.083 Uiso 1 1 calc R . . C33 C 0.5702(2) 0.54752(17) 0.24151(8) 0.0671(6) Uani 1 1 d . . . H33 H 0.5273 0.4937 0.2309 0.081 Uiso 1 1 calc R . . C34 C 0.7223(2) 0.56037(14) 0.23870(8) 0.0574(6) Uani 1 1 d . . . H34 H 0.7802 0.5148 0.2268 0.069 Uiso 1 1 calc R . . C35 C 1.03664(18) 0.58217(12) 0.22577(7) 0.0419(4) Uani 1 1 d . . . C36 C 1.0592(3) 0.58517(14) 0.17226(8) 0.0663(6) Uani 1 1 d . . . H36 H 1.025 0.6336 0.1518 0.08 Uiso 1 1 calc R . . C37 C 1.1317(3) 0.51775(16) 0.14814(10) 0.0852(8) Uani 1 1 d . . . H37 H 1.1457 0.5213 0.1118 0.102 Uiso 1 1 calc R . . C38 C 1.1831(3) 0.44590(15) 0.17708(11) 0.0758(7) Uani 1 1 d . . . H38 H 1.2342 0.4012 0.1609 0.091 Uiso 1 1 calc R . . C39 C 1.1585(3) 0.44065(15) 0.22996(10) 0.0767(7) Uani 1 1 d . . . H39 H 1.19 0.391 0.2498 0.092 Uiso 1 1 calc R . . C40 C 1.0875(2) 0.50824(13) 0.25438(9) 0.0649(6) Uani 1 1 d . . . H40 H 1.0734 0.5041 0.2907 0.078 Uiso 1 1 calc R . . C41 C 1.02828(19) 0.67007(11) 0.31137(7) 0.0415(4) Uani 1 1 d . . . C42 C 0.9658(2) 0.63536(15) 0.35492(8) 0.0625(6) Uani 1 1 d . . . H42 H 0.8749 0.6061 0.3498 0.075 Uiso 1 1 calc R . . C43 C 1.0355(3) 0.64319(17) 0.40618(9) 0.0768(7) Uani 1 1 d . . . H43 H 0.9915 0.619 0.4352 0.092 Uiso 1 1 calc R . . C44 C 1.1688(3) 0.68636(17) 0.41454(10) 0.0754(7) Uani 1 1 d . . . H44 H 1.2152 0.6925 0.4491 0.091 Uiso 1 1 calc R . . C45 C 1.2328(3) 0.72024(15) 0.37162(11) 0.0747(7) Uani 1 1 d . . . H45 H 1.3243 0.7487 0.377 0.09 Uiso 1 1 calc R . . C46 C 1.1632(2) 0.71279(13) 0.32002(8) 0.0563(5) Uani 1 1 d . . . H46 H 1.2078 0.7368 0.2911 0.068 Uiso 1 1 calc R . . N1 N 0.81367(17) 0.98729(10) 0.11832(6) 0.0531(4) Uani 1 1 d . . . N2 N 0.83102(17) 0.91674(10) 0.15027(6) 0.0519(4) 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 C1 0.0457(11) 0.0436(11) 0.0537(11) 0.0079(9) 0.0102(9) -0.0008(9) C2 0.0516(12) 0.0343(10) 0.0433(10) 0.0059(8) 0.0041(9) 0.0011(9) C3 0.0580(12) 0.0436(12) 0.0505(11) 0.0072(10) 0.0032(9) 0.0031(10) C4 0.0509(11) 0.0454(12) 0.0456(11) 0.0056(10) 0.0018(9) 0.0016(9) C5 0.0519(8) 0.0376(7) 0.0430(7) 0.0065(6) 0.0022(6) 0.0015(6) C6 0.0450(10) 0.0412(11) 0.0444(10) 0.0062(9) -0.0024(8) 0.0014(9) C7 0.0561(13) 0.0560(13) 0.0530(12) -0.0061(10) 0.0042(10) -0.0024(10) C8 0.0525(13) 0.0773(17) 0.0589(13) -0.0073(12) 0.0072(10) 0.0017(12) C9 0.0510(13) 0.0764(18) 0.1024(19) 0.0104(15) 0.0142(13) -0.0064(13) C10 0.0781(18) 0.0552(16) 0.182(3) 0.0020(18) 0.0446(19) -0.0140(14) C11 0.0685(15) 0.0465(14) 0.128(2) 0.0012(14) 0.0334(15) 0.0021(12) C12 0.0558(12) 0.0374(10) 0.0442(11) 0.0050(9) 0.0051(9) 0.0020(9) C13 0.1027(19) 0.0808(17) 0.0545(14) -0.0095(13) -0.0094(13) 0.0325(14) C14 0.144(3) 0.086(2) 0.0586(15) -0.0158(15) 0.0035(16) 0.0305(19) C15 0.103(2) 0.0789(18) 0.0779(18) -0.0192(15) 0.0338(16) 0.0093(16) C16 0.0708(17) 0.109(2) 0.124(2) -0.041(2) 0.0035(17) 0.0275(16) C17 0.0620(14) 0.0924(18) 0.0796(16) -0.0287(14) -0.0058(12) 0.0215(13) C18 0.0423(10) 0.0453(11) 0.0415(10) -0.0004(9) 0.0032(8) 0.0034(9) C19 0.0523(12) 0.0547(13) 0.0540(12) -0.0038(10) 0.0088(10) -0.0040(10) C20 0.0483(12) 0.0753(16) 0.0756(16) -0.0211(13) 0.0081(11) -0.0120(11) C21 0.0507(13) 0.103(2) 0.0580(14) -0.0150(14) -0.0033(11) 0.0033(13) C22 0.0749(16) 0.0899(18) 0.0528(13) 0.0107(13) -0.0115(12) 0.0047(14) C23 0.0666(13) 0.0609(14) 0.0527(12) 0.0126(11) -0.0080(10) -0.0045(11) C24 0.0426(11) 0.0420(11) 0.0483(11) 0.0070(9) 0.0035(8) 0.0059(9) C25 0.0466(11) 0.0330(10) 0.0393(10) 0.0004(8) 0.0026(8) 0.0016(8) C26 0.0519(8) 0.0376(7) 0.0430(7) 0.0065(6) 0.0022(6) 0.0015(6) C27 0.0447(10) 0.0419(11) 0.0438(10) 0.0028(9) 0.0060(8) 0.0001(9) C28 0.0423(10) 0.0361(10) 0.0428(10) 0.0074(8) 0.0046(8) -0.0016(8) C29 0.0420(10) 0.0459(11) 0.0420(10) 0.0081(9) 0.0008(8) -0.0031(9) C30 0.0455(12) 0.0557(14) 0.0921(17) -0.0007(12) 0.0103(11) -0.0009(10) C31 0.0505(13) 0.0772(17) 0.1022(19) 0.0081(15) 0.0137(12) 0.0111(13) C32 0.0461(12) 0.0937(19) 0.0676(15) 0.0179(14) 0.0018(11) -0.0064(14) C33 0.0599(14) 0.0810(17) 0.0592(13) 0.0020(13) -0.0011(11) -0.0262(13) C34 0.0527(13) 0.0611(14) 0.0584(13) -0.0017(11) 0.0048(10) -0.0096(11) C35 0.0415(10) 0.0380(10) 0.0460(11) 0.0033(9) 0.0035(8) -0.0030(8) C36 0.0966(17) 0.0460(12) 0.0599(14) 0.0118(11) 0.0271(12) 0.0122(12) C37 0.129(2) 0.0563(15) 0.0779(16) 0.0018(13) 0.0498(16) 0.0095(15) C38 0.0780(16) 0.0510(15) 0.100(2) -0.0163(14) 0.0174(14) 0.0086(12) C39 0.1012(19) 0.0479(14) 0.0767(17) -0.0049(12) -0.0162(14) 0.0199(13) C40 0.0946(17) 0.0439(12) 0.0540(13) 0.0033(10) -0.0061(12) 0.0118(12) C41 0.0406(10) 0.0395(10) 0.0446(11) 0.0020(8) 0.0045(8) 0.0006(8) C42 0.0532(12) 0.0847(16) 0.0502(12) 0.0078(12) 0.0080(10) -0.0079(11) C43 0.0783(17) 0.110(2) 0.0426(12) 0.0054(13) 0.0094(11) 0.0078(15) C44 0.0869(18) 0.0852(18) 0.0506(14) -0.0148(13) -0.0137(13) 0.0151(14) C45 0.0684(15) 0.0639(15) 0.0860(18) -0.0029(13) -0.0249(14) -0.0103(12) C46 0.0514(12) 0.0539(13) 0.0621(13) 0.0069(11) -0.0034(10) -0.0059(10) N1 0.0495(10) 0.0464(10) 0.0632(11) 0.0149(9) 0.0045(8) 0.0060(8) N2 0.0466(9) 0.0457(9) 0.0637(10) 0.0144(9) 0.0068(8) 0.0030(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C24 1.361(2) . ? C1 C2 1.389(2) . ? C1 H1 0.93 . ? C2 N1 1.338(2) . ? C2 C3 1.437(2) . ? C3 C4 1.194(2) . ? C4 C5 1.483(2) . ? C5 C12 1.545(3) . ? C5 C6 1.542(3) . ? C5 C18 1.546(2) . ? C6 C11 1.375(3) . ? C6 C7 1.379(3) . ? C7 C8 1.378(3) . ? C7 H7 0.93 . ? C8 C9 1.349(3) . ? C8 H8 0.93 . ? C9 C10 1.349(4) . ? C9 H9 0.93 . ? C10 C11 1.386(3) . ? C10 H10 0.93 . ? C11 H11 0.93 . ? C12 C17 1.358(3) . ? C12 C13 1.378(3) . ? C13 C14 1.371(3) . ? C13 H13 0.93 . ? C14 C15 1.354(3) . ? C14 H14 0.93 . ? C15 C16 1.349(3) . ? C15 H15 0.93 . ? C16 C17 1.393(3) . ? C16 H16 0.93 . ? C17 H17 0.93 . ? C18 C23 1.378(3) . ? C18 C19 1.381(3) . ? C19 C20 1.389(3) . ? C19 H19 0.93 . ? C20 C21 1.368(3) . ? C20 H20 0.93 . ? C21 C22 1.363(3) . ? C21 H21 0.93 . ? C22 C23 1.384(3) . ? C22 H22 0.93 . ? C23 H23 0.93 . ? C24 C25 1.387(2) . ? C24 H24 0.93 . ? C25 N2 1.343(2) . ? C25 C26 1.433(2) . ? C26 C27 1.194(2) . ? C27 C28 1.481(2) . ? C28 C35 1.546(2) . ? C28 C29 1.549(2) . ? C28 C41 1.550(2) . ? C29 C34 1.371(3) . ? C29 C30 1.381(3) . ? C30 C31 1.381(3) . ? C30 H30 0.93 . ? C31 C32 1.361(3) . ? C31 H31 0.93 . ? C32 C33 1.362(3) . ? C32 H32 0.93 . ? C33 C34 1.392(3) . ? C33 H33 0.93 . ? C34 H34 0.93 . ? C35 C36 1.370(3) . ? C35 C40 1.383(2) . ? C36 C37 1.378(3) . ? C36 H36 0.93 . ? C37 C38 1.363(3) . ? C37 H37 0.93 . ? C38 C39 1.361(3) . ? C38 H38 0.93 . ? C39 C40 1.377(3) . ? C39 H39 0.93 . ? C40 H40 0.93 . ? C41 C42 1.373(3) . ? C41 C46 1.376(2) . ? C42 C43 1.380(3) . ? C42 H42 0.93 . ? C43 C44 1.367(3) . ? C43 H43 0.93 . ? C44 C45 1.361(3) . ? C44 H44 0.93 . ? C45 C46 1.387(3) . ? C45 H45 0.93 . ? C46 H46 0.93 . ? N1 N2 1.333(2) . ? 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 C24 C1 C2 117.86(17) . . ? C24 C1 H1 121.1 . . ? C2 C1 H1 121.1 . . ? N1 C2 C1 122.36(16) . . ? N1 C2 C3 115.10(16) . . ? C1 C2 C3 122.53(17) . . ? C4 C3 C2 178.3(2) . . ? C3 C4 C5 178.0(2) . . ? C4 C5 C12 106.90(15) . . ? C4 C5 C6 107.77(14) . . ? C12 C5 C6 112.59(15) . . ? C4 C5 C18 109.85(14) . . ? C12 C5 C18 110.79(14) . . ? C6 C5 C18 108.86(14) . . ? C11 C6 C7 116.08(19) . . ? C11 C6 C5 123.86(18) . . ? C7 C6 C5 119.99(17) . . ? C6 C7 C8 122.2(2) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 119.0(2) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.2(2) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C6 C11 C10 121.2(2) . . ? C6 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C17 C12 C13 117.12(19) . . ? C17 C12 C5 123.40(17) . . ? C13 C12 C5 119.48(17) . . ? C14 C13 C12 121.6(2) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C15 C14 C13 120.7(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 118.8(2) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 120.9(2) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 121.0(2) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C23 C18 C19 117.81(17) . . ? C23 C18 C5 119.62(16) . . ? C19 C18 C5 122.49(16) . . ? C18 C19 C20 120.7(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.4(2) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C18 C23 C22 121.3(2) . . ? C18 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C1 C24 C25 117.99(16) . . ? C1 C24 H24 121 . . ? C25 C24 H24 121 . . ? N2 C25 C24 122.38(16) . . ? N2 C25 C26 114.78(16) . . ? C24 C25 C26 122.82(15) . . ? C27 C26 C25 176.85(19) . . ? C26 C27 C28 175.13(18) . . ? C27 C28 C35 109.42(14) . . ? C27 C28 C29 106.78(13) . . ? C35 C28 C29 111.65(14) . . ? C27 C28 C41 109.43(14) . . ? C35 C28 C41 109.25(13) . . ? C29 C28 C41 110.27(14) . . ? C34 C29 C30 117.90(18) . . ? C34 C29 C28 123.48(17) . . ? C30 C29 C28 118.59(16) . . ? C31 C30 C29 121.1(2) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C32 C31 C30 120.5(2) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C33 119.1(2) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C32 C33 C34 120.8(2) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C29 C34 C33 120.5(2) . . ? C29 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C36 C35 C40 117.36(18) . . ? C36 C35 C28 121.49(16) . . ? C40 C35 C28 121.15(17) . . ? C35 C36 C37 121.3(2) . . ? C35 C36 H36 119.4 . . ? C37 C36 H36 119.4 . . ? C38 C37 C36 120.7(2) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C39 C38 C37 119.0(2) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C38 C39 C40 120.6(2) . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C39 C40 C35 121.1(2) . . ? C39 C40 H40 119.4 . . ? C35 C40 H40 119.4 . . ? C42 C41 C46 118.26(18) . . ? C42 C41 C28 122.13(16) . . ? C46 C41 C28 119.52(17) . . ? C41 C42 C43 121.2(2) . . ? C41 C42 H42 119.4 . . ? C43 C42 H42 119.4 . . ? C44 C43 C42 120.3(2) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C45 C44 C43 119.1(2) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? C44 C45 C46 120.9(2) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C41 C46 C45 120.3(2) . . ? C41 C46 H46 119.9 . . ? C45 C46 H46 119.9 . . ? N2 N1 C2 119.89(14) . . ? N1 N2 C25 119.50(15) . . ? 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 C24 C1 C2 N1 -0.1(3) . . . . ? C24 C1 C2 C3 -179.24(17) . . . . ? C4 C5 C6 C11 -131.1(2) . . . . ? C12 C5 C6 C11 -13.5(2) . . . . ? C18 C5 C6 C11 109.8(2) . . . . ? C4 C5 C6 C7 52.1(2) . . . . ? C12 C5 C6 C7 169.73(15) . . . . ? C18 C5 C6 C7 -67.0(2) . . . . ? C11 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C8 176.55(16) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? C7 C6 C11 C10 0.5(3) . . . . ? C5 C6 C11 C10 -176.5(2) . . . . ? C9 C10 C11 C6 -0.3(4) . . . . ? C4 C5 C12 C17 -127.2(2) . . . . ? C6 C5 C12 C17 114.6(2) . . . . ? C18 C5 C12 C17 -7.5(3) . . . . ? C4 C5 C12 C13 53.5(2) . . . . ? C6 C5 C12 C13 -64.7(2) . . . . ? C18 C5 C12 C13 173.14(18) . . . . ? C17 C12 C13 C14 0.2(4) . . . . ? C5 C12 C13 C14 179.5(2) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C13 C12 C17 C16 -0.6(4) . . . . ? C5 C12 C17 C16 -179.9(2) . . . . ? C15 C16 C17 C12 0.5(5) . . . . ? C4 C5 C18 C23 -162.08(18) . . . . ? C12 C5 C18 C23 80.0(2) . . . . ? C6 C5 C18 C23 -44.3(2) . . . . ? C4 C5 C18 C19 21.5(2) . . . . ? C12 C5 C18 C19 -96.4(2) . . . . ? C6 C5 C18 C19 139.25(18) . . . . ? C23 C18 C19 C20 -1.2(3) . . . . ? C5 C18 C19 C20 175.34(18) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 0.9(3) . . . . ? C20 C21 C22 C23 -0.9(4) . . . . ? C19 C18 C23 C22 1.2(3) . . . . ? C5 C18 C23 C22 -175.4(2) . . . . ? C21 C22 C23 C18 -0.2(4) . . . . ? C2 C1 C24 C25 -0.7(3) . . . . ? C1 C24 C25 N2 0.6(3) . . . . ? C1 C24 C25 C26 179.19(17) . . . . ? C27 C28 C29 C34 128.87(18) . . . . ? C35 C28 C29 C34 9.3(2) . . . . ? C41 C28 C29 C34 -112.32(19) . . . . ? C27 C28 C29 C30 -53.0(2) . . . . ? C35 C28 C29 C30 -172.60(17) . . . . ? C41 C28 C29 C30 65.8(2) . . . . ? C34 C29 C30 C31 1.3(3) . . . . ? C28 C29 C30 C31 -176.87(19) . . . . ? C29 C30 C31 C32 -1.4(3) . . . . ? C30 C31 C32 C33 0.3(3) . . . . ? C31 C32 C33 C34 0.9(3) . . . . ? C30 C29 C34 C33 -0.1(3) . . . . ? C28 C29 C34 C33 177.95(17) . . . . ? C32 C33 C34 C29 -1.0(3) . . . . ? C27 C28 C35 C36 -24.5(2) . . . . ? C29 C28 C35 C36 93.5(2) . . . . ? C41 C28 C35 C36 -144.26(18) . . . . ? C27 C28 C35 C40 156.04(17) . . . . ? C29 C28 C35 C40 -86.0(2) . . . . ? C41 C28 C35 C40 36.3(2) . . . . ? C40 C35 C36 C37 -1.0(3) . . . . ? C28 C35 C36 C37 179.5(2) . . . . ? C35 C36 C37 C38 0.0(4) . . . . ? C36 C37 C38 C39 1.6(4) . . . . ? C37 C38 C39 C40 -2.3(4) . . . . ? C38 C39 C40 C35 1.3(4) . . . . ? C36 C35 C40 C39 0.3(3) . . . . ? C28 C35 C40 C39 179.81(19) . . . . ? C27 C28 C41 C42 140.70(19) . . . . ? C35 C28 C41 C42 -99.5(2) . . . . ? C29 C28 C41 C42 23.5(2) . . . . ? C27 C28 C41 C46 -42.9(2) . . . . ? C35 C28 C41 C46 76.9(2) . . . . ? C29 C28 C41 C46 -160.05(16) . . . . ? C46 C41 C42 C43 0.3(3) . . . . ? C28 C41 C42 C43 176.74(19) . . . . ? C41 C42 C43 C44 0.3(4) . . . . ? C42 C43 C44 C45 -1.0(4) . . . . ? C43 C44 C45 C46 1.2(4) . . . . ? C42 C41 C46 C45 -0.1(3) . . . . ? C28 C41 C46 C45 -176.68(18) . . . . ? C44 C45 C46 C41 -0.6(3) . . . . ? C1 C2 N1 N2 1.2(3) . . . . ? C3 C2 N1 N2 -179.63(16) . . . . ? C2 N1 N2 C25 -1.3(3) . . . . ? C24 C25 N2 N1 0.5(3) . . . . ? C26 C25 N2 N1 -178.24(16) . . . . ?