#------------------------------------------------------------------------------ #$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/66/2216649.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2216649 loop_ _publ_author_name 'Juan Li' 'Yan Hu' 'Zi-hua Wang' _publ_section_title 2,6-Diethyl-8b,8c-diphenylperhydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione _journal_coeditor_code LW2043 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4777 _journal_page_last o4777 _journal_paper_doi 10.1107/S1600536807058400 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C24 H28 N6 O2' _chemical_formula_moiety 'C24 H28 N6 O2' _chemical_formula_sum 'C24 H28 N6 O2' _chemical_formula_weight 432.52 _chemical_name_systematic ; 2,6-Diethyl-8b,8c-diphenylperhydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-4,8-dione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 76.885(2) _cell_angle_beta 73.2330(10) _cell_angle_gamma 84.5760(10) _cell_formula_units_Z 2 _cell_length_a 8.6963(9) _cell_length_b 10.3704(10) _cell_length_c 13.0294(13) _cell_measurement_reflns_used 1908 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 23.68 _cell_measurement_theta_min 2.33 _cell_volume 1095.21(19) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker SMART 4K CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1047 _diffrn_reflns_av_sigmaI/netI 0.1100 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7080 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 1.67 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.251 _refine_diff_density_min -0.233 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 4255 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.986 _refine_ls_R_factor_all 0.0902 _refine_ls_R_factor_gt 0.0605 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1445 _refine_ls_wR_factor_ref 0.1636 _reflns_number_gt 2885 _reflns_number_total 4255 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lw2043.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2216649 _cod_database_fobs_code 2216649 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy C C1 0.0890(4) -0.2902(3) 0.9644(2) 0.0645(8) Uani d . 1 H H1A 0.1391 -0.2709 1.0157 0.097 Uiso calc R 1 H H1B 0.0987 -0.3835 0.9661 0.097 Uiso calc R 1 H H1C -0.0226 -0.2635 0.9839 0.097 Uiso calc R 1 C C2 0.1698(3) -0.2160(2) 0.8515(2) 0.0457(6) Uani d . 1 H H2A 0.2850 -0.2313 0.8377 0.055 Uiso calc R 1 H H2B 0.1362 -0.2511 0.7986 0.055 Uiso calc R 1 C C3 0.1908(3) -0.0040(2) 0.90159(19) 0.0391(6) Uani d . 1 H H3A 0.1646 -0.0551 0.9763 0.047 Uiso calc R 1 H H3B 0.1337 0.0809 0.9023 0.047 Uiso calc R 1 C C4 0.1900(3) -0.0064(2) 0.71965(19) 0.0393(6) Uani d . 1 H H4A 0.1325 0.0783 0.7091 0.047 Uiso calc R 1 H H4B 0.1638 -0.0592 0.6748 0.047 Uiso calc R 1 C C5 0.4739(3) -0.0717(2) 0.89922(18) 0.0328(5) Uani d . 1 C C6 0.4730(3) -0.0729(2) 0.63566(17) 0.0305(5) Uani d . 1 C C7 0.4254(2) 0.0817(2) 0.74911(16) 0.0283(5) Uani d . 1 C C8 0.3877(2) 0.2307(2) 0.72892(17) 0.0299(5) Uani d . 1 C C9 0.3722(3) 0.2996(2) 0.8109(2) 0.0437(6) Uani d . 1 H H9 0.3805 0.2550 0.8797 0.052 Uiso calc R 1 C C10 0.3441(4) 0.4357(3) 0.7899(2) 0.0599(8) Uani d . 1 H H10 0.3345 0.4822 0.8447 0.072 Uiso calc R 1 C C11 0.3304(3) 0.5026(3) 0.6891(3) 0.0574(8) Uani d . 1 H H11 0.3105 0.5937 0.6760 0.069 Uiso calc R 1 C C12 0.3462(3) 0.4342(3) 0.6077(2) 0.0492(7) Uani d . 1 H H12 0.3373 0.4794 0.5392 0.059 Uiso calc R 1 C C13 0.3753(3) 0.2983(2) 0.62682(19) 0.0385(6) Uani d . 1 H H13 0.3866 0.2526 0.5712 0.046 Uiso calc R 1 C C14 0.6075(2) 0.0377(2) 0.72159(16) 0.0279(5) Uani d . 1 C C15 0.7302(2) 0.1463(2) 0.67807(18) 0.0314(5) Uani d . 1 C C16 0.7865(3) 0.1967(2) 0.7500(2) 0.0418(6) Uani d . 1 H H16 0.7484 0.1649 0.8252 0.050 Uiso calc R 1 C C17 0.8994(3) 0.2942(3) 0.7098(2) 0.0519(7) Uani d . 1 H H17 0.9373 0.3277 0.7580 0.062 Uiso calc R 1 C C18 0.9557(3) 0.3416(3) 0.5991(2) 0.0536(7) Uani d . 1 H H18 1.0326 0.4064 0.5724 0.064 Uiso calc R 1 C C19 0.8986(3) 0.2936(3) 0.5272(2) 0.0495(7) Uani d . 1 H H19 0.9360 0.3267 0.4521 0.059 Uiso calc R 1 C C20 0.7859(3) 0.1962(2) 0.56666(19) 0.0404(6) Uani d . 1 H H20 0.7472 0.1641 0.5181 0.048 Uiso calc R 1 C C21 0.7575(3) -0.1426(3) 0.8167(2) 0.0436(6) Uani d . 1 H H21A 0.8566 -0.0956 0.7969 0.052 Uiso calc R 1 H H21B 0.7471 -0.2001 0.8882 0.052 Uiso calc R 1 C C22 0.7572(3) -0.1410(2) 0.6332(2) 0.0455(6) Uani d . 1 H H22A 0.7485 -0.1976 0.5853 0.055 Uiso calc R 1 H H22B 0.8559 -0.0931 0.5989 0.055 Uiso calc R 1 C C23 0.6583(4) -0.3353(3) 0.7767(2) 0.0571(7) Uani d . 1 H H23A 0.6630 -0.3773 0.7165 0.068 Uiso calc R 1 H H23B 0.5492 -0.3016 0.8023 0.068 Uiso calc R 1 C C24 0.6991(5) -0.4366(3) 0.8681(3) 0.0896(12) Uani d . 1 H H24A 0.8115 -0.4602 0.8471 0.134 Uiso calc R 1 H H24B 0.6372 -0.5139 0.8828 0.134 Uiso calc R 1 H H24C 0.6745 -0.4003 0.9327 0.134 Uiso calc R 1 N N1 0.1345(2) -0.07304(19) 0.83424(16) 0.0393(5) Uani d . 1 N N2 0.3631(2) 0.01826(17) 0.86419(14) 0.0304(4) Uani d . 1 N N3 0.3625(2) 0.01628(17) 0.68186(14) 0.0303(4) Uani d . 1 N N4 0.6222(2) -0.04582(18) 0.82483(14) 0.0316(4) Uani d . 1 N N5 0.6212(2) -0.04532(18) 0.64235(14) 0.0323(4) Uani d . 1 N N6 0.7685(2) -0.2239(2) 0.73700(17) 0.0449(5) Uani d . 1 O O1 0.4475(2) -0.15622(16) 0.98420(12) 0.0451(5) Uani d . 1 O O2 0.4458(2) -0.15742(16) 0.59266(12) 0.0425(4) Uani d . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.061(2) 0.0429(16) 0.078(2) -0.0049(14) -0.0077(16) -0.0041(15) C2 0.0360(14) 0.0336(14) 0.0638(17) -0.0038(11) -0.0060(12) -0.0119(12) C3 0.0284(13) 0.0375(13) 0.0457(14) -0.0013(10) 0.0016(10) -0.0125(11) C4 0.0277(13) 0.0391(14) 0.0544(15) -0.0013(11) -0.0134(11) -0.0134(12) C5 0.0341(13) 0.0350(13) 0.0306(12) -0.0086(10) -0.0067(10) -0.0092(10) C6 0.0332(13) 0.0301(12) 0.0289(12) -0.0025(10) -0.0069(10) -0.0090(10) C7 0.0263(11) 0.0292(12) 0.0288(11) -0.0020(9) -0.0036(9) -0.0097(9) C8 0.0221(11) 0.0277(12) 0.0385(13) -0.0017(9) -0.0044(9) -0.0087(10) C9 0.0537(16) 0.0340(13) 0.0438(14) -0.0018(12) -0.0093(12) -0.0142(11) C10 0.082(2) 0.0369(15) 0.0650(19) 0.0007(15) -0.0156(17) -0.0256(14) C11 0.0582(19) 0.0290(14) 0.082(2) 0.0036(13) -0.0156(16) -0.0132(15) C12 0.0477(16) 0.0362(14) 0.0576(17) -0.0016(12) -0.0143(13) 0.0022(12) C13 0.0370(14) 0.0333(13) 0.0438(14) -0.0005(11) -0.0081(11) -0.0093(11) C14 0.0219(11) 0.0313(12) 0.0301(11) -0.0021(9) -0.0039(9) -0.0093(9) C15 0.0218(11) 0.0306(12) 0.0393(13) 0.0002(9) -0.0041(9) -0.0081(10) C16 0.0388(14) 0.0419(14) 0.0444(14) -0.0075(11) -0.0085(11) -0.0095(11) C17 0.0467(16) 0.0436(16) 0.0706(19) -0.0145(13) -0.0218(14) -0.0098(14) C18 0.0341(15) 0.0373(14) 0.082(2) -0.0126(12) -0.0143(14) 0.0053(14) C19 0.0358(14) 0.0463(15) 0.0527(16) -0.0070(12) -0.0007(12) 0.0046(13) C20 0.0354(14) 0.0414(14) 0.0401(14) -0.0058(11) -0.0043(11) -0.0059(11) C21 0.0295(13) 0.0438(15) 0.0566(16) 0.0015(11) -0.0146(12) -0.0058(12) C22 0.0357(14) 0.0437(15) 0.0538(16) 0.0073(12) -0.0015(12) -0.0214(13) C23 0.0547(18) 0.0364(15) 0.080(2) 0.0035(13) -0.0194(15) -0.0142(14) C24 0.112(3) 0.0472(19) 0.108(3) -0.005(2) -0.039(2) 0.0013(19) N1 0.0267(10) 0.0334(11) 0.0545(13) -0.0037(9) -0.0057(9) -0.0086(9) N2 0.0253(10) 0.0320(10) 0.0300(10) -0.0041(8) 0.0005(8) -0.0078(8) N3 0.0256(10) 0.0302(10) 0.0369(10) -0.0012(8) -0.0074(8) -0.0118(8) N4 0.0255(10) 0.0324(10) 0.0352(10) -0.0023(8) -0.0066(8) -0.0051(8) N5 0.0282(10) 0.0330(10) 0.0342(10) 0.0028(8) -0.0027(8) -0.0136(8) N6 0.0329(12) 0.0394(12) 0.0598(14) 0.0054(9) -0.0105(10) -0.0110(10) O1 0.0485(11) 0.0458(10) 0.0347(9) -0.0089(8) -0.0067(8) 0.0011(8) O2 0.0494(11) 0.0406(9) 0.0439(10) -0.0024(8) -0.0132(8) -0.0206(8) 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 C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 N1 C2 C1 113.7(2) N1 C2 H2A 108.8 C1 C2 H2A 108.8 N1 C2 H2B 108.8 C1 C2 H2B 108.8 H2A C2 H2B 107.7 N1 C3 N2 113.90(18) N1 C3 H3A 108.8 N2 C3 H3A 108.8 N1 C3 H3B 108.8 N2 C3 H3B 108.8 H3A C3 H3B 107.7 N1 C4 N3 113.84(18) N1 C4 H4A 108.8 N3 C4 H4A 108.8 N1 C4 H4B 108.8 N3 C4 H4B 108.8 H4A C4 H4B 107.7 O1 C5 N2 126.2(2) O1 C5 N4 125.5(2) N2 C5 N4 108.24(18) O2 C6 N3 126.1(2) O2 C6 N5 126.1(2) N3 C6 N5 107.80(17) N2 C7 N3 109.20(15) N2 C7 C8 111.82(17) N3 C7 C8 112.05(17) N2 C7 C14 103.45(16) N3 C7 C14 103.08(16) C8 C7 C14 116.52(16) C9 C8 C13 119.7(2) C9 C8 C7 120.3(2) C13 C8 C7 119.94(19) C8 C9 C10 119.5(2) C8 C9 H9 120.2 C10 C9 H9 120.2 C11 C10 C9 120.8(2) C11 C10 H10 119.6 C9 C10 H10 119.6 C10 C11 C12 119.6(2) C10 C11 H11 120.2 C12 C11 H11 120.2 C11 C12 C13 120.5(2) C11 C12 H12 119.8 C13 C12 H12 119.8 C8 C13 C12 119.8(2) C8 C13 H13 120.1 C12 C13 H13 120.1 N4 C14 N5 109.15(17) N4 C14 C15 111.90(16) N5 C14 C15 111.68(17) N4 C14 C7 102.98(15) N5 C14 C7 102.89(15) C15 C14 C7 117.46(18) C20 C15 C16 119.4(2) C20 C15 C14 120.36(19) C16 C15 C14 120.3(2) C17 C16 C15 119.9(2) C17 C16 H16 120.0 C15 C16 H16 120.0 C18 C17 C16 120.3(2) C18 C17 H17 119.9 C16 C17 H17 119.9 C17 C18 C19 120.2(2) C17 C18 H18 119.9 C19 C18 H18 119.9 C18 C19 C20 119.9(2) C18 C19 H19 120.0 C20 C19 H19 120.0 C19 C20 C15 120.3(2) C19 C20 H20 119.8 C15 C20 H20 119.8 N6 C21 N4 113.91(18) N6 C21 H21A 108.8 N4 C21 H21A 108.8 N6 C21 H21B 108.8 N4 C21 H21B 108.8 H21A C21 H21B 107.7 N6 C22 N5 114.39(19) N6 C22 H22A 108.7 N5 C22 H22A 108.7 N6 C22 H22B 108.7 N5 C22 H22B 108.7 H22A C22 H22B 107.6 N6 C23 C24 112.2(2) N6 C23 H23A 109.2 C24 C23 H23A 109.2 N6 C23 H23B 109.2 C24 C23 H23B 109.2 H23A C23 H23B 107.9 C23 C24 H24A 109.5 C23 C24 H24B 109.5 H24A C24 H24B 109.5 C23 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C4 N1 C3 109.47(17) C4 N1 C2 112.71(19) C3 N1 C2 115.28(19) C5 N2 C7 111.13(17) C5 N2 C3 122.64(18) C7 N2 C3 115.74(17) C6 N3 C4 122.70(18) C6 N3 C7 111.66(17) C4 N3 C7 115.74(17) C5 N4 C14 111.48(18) C5 N4 C21 123.05(19) C14 N4 C21 115.96(18) C6 N5 C14 111.84(17) C6 N5 C22 123.01(19) C14 N5 C22 115.18(17) C22 N6 C21 110.28(18) C22 N6 C23 113.4(2) C21 N6 C23 114.3(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.497(3) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C2 N1 1.465(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 N1 1.457(3) C3 N2 1.459(3) C3 H3A 0.9700 C3 H3B 0.9700 C4 N1 1.456(3) C4 N3 1.461(3) C4 H4A 0.9700 C4 H4B 0.9700 C5 O1 1.224(2) C5 N2 1.377(3) C5 N4 1.379(3) C6 O2 1.216(2) C6 N3 1.375(3) C6 N5 1.377(3) C7 N2 1.458(3) C7 N3 1.464(2) C7 C8 1.528(3) C7 C14 1.566(3) C8 C9 1.384(3) C8 C13 1.385(3) C9 C10 1.387(4) C9 H9 0.9300 C10 C11 1.371(4) C10 H10 0.9300 C11 C12 1.373(4) C11 H11 0.9300 C12 C13 1.387(3) C12 H12 0.9300 C13 H13 0.9300 C14 N4 1.458(3) C14 N5 1.461(3) C14 C15 1.522(3) C15 C20 1.382(3) C15 C16 1.388(3) C16 C17 1.382(3) C16 H16 0.9300 C17 C18 1.370(4) C17 H17 0.9300 C18 C19 1.378(4) C18 H18 0.9300 C19 C20 1.380(3) C19 H19 0.9300 C20 H20 0.9300 C21 N6 1.458(3) C21 N4 1.468(3) C21 H21A 0.9700 C21 H21B 0.9700 C22 N6 1.453(3) C22 N5 1.466(3) C22 H22A 0.9700 C22 H22B 0.9700 C23 N6 1.474(3) C23 C24 1.500(4) C23 H23A 0.9700 C23 H23B 0.9700 C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C16 H16 O1 2_657 0.93 2.56 3.427(3) 154.9 yes C13 H13 O2 2_656 0.93 2.56 3.410(3) 152.4 yes C20 H20 O2 2_656 0.93 2.52 3.387(3) 154.7 yes 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 N2 C7 C8 C9 29.1(3) N3 C7 C8 C9 152.1(2) C14 C7 C8 C9 -89.6(2) N2 C7 C8 C13 -153.51(19) N3 C7 C8 C13 -30.5(3) C14 C7 C8 C13 87.8(2) C13 C8 C9 C10 0.1(4) C7 C8 C9 C10 177.5(2) C8 C9 C10 C11 0.5(4) C9 C10 C11 C12 -0.6(4) C10 C11 C12 C13 0.2(4) C9 C8 C13 C12 -0.5(3) C7 C8 C13 C12 -177.9(2) C11 C12 C13 C8 0.4(4) N2 C7 C14 N4 0.65(18) N3 C7 C14 N4 -113.10(16) C8 C7 C14 N4 123.77(18) N2 C7 C14 N5 114.10(16) N3 C7 C14 N5 0.36(19) C8 C7 C14 N5 -122.78(18) N2 C7 C14 C15 -122.80(18) N3 C7 C14 C15 123.45(18) C8 C7 C14 C15 0.3(3) N4 C14 C15 C20 151.3(2) N5 C14 C15 C20 28.6(3) C7 C14 C15 C20 -89.9(3) N4 C14 C15 C16 -29.1(3) N5 C14 C15 C16 -151.8(2) C7 C14 C15 C16 89.7(2) C20 C15 C16 C17 -1.1(4) C14 C15 C16 C17 179.2(2) C15 C16 C17 C18 0.1(4) C16 C17 C18 C19 0.8(4) C17 C18 C19 C20 -0.8(4) C18 C19 C20 C15 -0.2(4) C16 C15 C20 C19 1.1(4) C14 C15 C20 C19 -179.2(2) N3 C4 N1 C3 51.3(2) N3 C4 N1 C2 -78.4(2) N2 C3 N1 C4 -51.5(2) N2 C3 N1 C2 76.7(3) C1 C2 N1 C4 -169.8(2) C1 C2 N1 C3 63.6(3) O1 C5 N2 C7 -166.2(2) N4 C5 N2 C7 16.9(2) O1 C5 N2 C3 -23.0(3) N4 C5 N2 C3 160.07(18) N3 C7 N2 C5 98.73(19) C8 C7 N2 C5 -136.70(18) C14 C7 N2 C5 -10.5(2) N3 C7 N2 C3 -47.2(2) C8 C7 N2 C3 77.4(2) C14 C7 N2 C3 -156.44(17) N1 C3 N2 C5 -89.5(2) N1 C3 N2 C7 52.2(3) O2 C6 N3 C4 22.0(3) N5 C6 N3 C4 -160.69(18) O2 C6 N3 C7 166.1(2) N5 C6 N3 C7 -16.6(2) N1 C4 N3 C6 91.0(2) N1 C4 N3 C7 -51.7(3) N2 C7 N3 C6 -99.8(2) C8 C7 N3 C6 135.78(19) C14 C7 N3 C6 9.7(2) N2 C7 N3 C4 47.0(2) C8 C7 N3 C4 -77.4(2) C14 C7 N3 C4 156.51(17) O1 C5 N4 C14 166.56(19) N2 C5 N4 C14 -16.5(2) O1 C5 N4 C21 21.7(3) N2 C5 N4 C21 -161.32(18) N5 C14 N4 C5 -99.4(2) C15 C14 N4 C5 136.47(19) C7 C14 N4 C5 9.4(2) N5 C14 N4 C21 48.1(2) C15 C14 N4 C21 -76.0(2) C7 C14 N4 C21 156.92(17) N6 C21 N4 C5 92.6(3) N6 C21 N4 C14 -50.8(3) O2 C6 N5 C14 -165.8(2) N3 C6 N5 C14 16.9(2) O2 C6 N5 C22 -22.0(3) N3 C6 N5 C22 160.70(19) N4 C14 N5 C6 98.52(19) C15 C14 N5 C6 -137.22(19) C7 C14 N5 C6 -10.3(2) N4 C14 N5 C22 -48.3(2) C15 C14 N5 C22 76.0(2) C7 C14 N5 C22 -157.17(17) N6 C22 N5 C6 -90.8(2) N6 C22 N5 C14 51.9(3) N5 C22 N6 C21 -49.9(3) N5 C22 N6 C23 79.8(3) N4 C21 N6 C22 49.0(3) N4 C21 N6 C23 -80.2(3) C24 C23 N6 C22 166.3(3) C24 C23 N6 C21 -66.1(3)