#------------------------------------------------------------------------------ #$Date: 2015-07-01 04:35:18 +0300 (Wed, 01 Jul 2015) $ #$Revision: 139826 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/52/07/1520708.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_1520708 loop_ _publ_author_name 'Wang, Qi' 'Tang, Xuli' 'Luo, Xiangchao' 'de Voogd, Nicole J.' 'Li, Pinglin' 'Li, Guoqiang' _publ_section_title ; (+)- and (−)-Spiroreticulatine, A Pair of Unusual Spiro Bisheterocyclic Quinoline-imidazole Alkaloids from the South China Sea SpongeFascaplysinopsis reticulata ; _journal_name_full 'Organic Letters' _journal_page_first 150630104033003 _journal_paper_doi 10.1021/acs.orglett.5b01503 _journal_year 2015 _chemical_formula_moiety 'C15 H15 N3 O4' _chemical_formula_sum 'C15 H15 N3 O4' _chemical_formula_weight 301.30 _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 iterative _audit_creation_date 2015-06-17 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _cell_angle_alpha 90 _cell_angle_beta 107.894(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4762(3) _cell_length_b 7.95324(15) _cell_length_c 16.5869(5) _cell_measurement_reflns_used 4682 _cell_measurement_temperature 294.39(10) _cell_measurement_theta_max 69.5060 _cell_measurement_theta_min 4.0020 _cell_volume 1440.70(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 294.39(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_details ; 1 omega -68.00 -19.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 90.0000 49 2 omega -13.00 14.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 90.0000 27 3 omega -20.00 24.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -71.0000 -166.0000 44 4 omega 29.00 62.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 30.0000 33 5 omega -16.00 35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -38.0000 -180.0000 51 6 omega 24.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -125.0000 150.0000 88 7 omega -7.00 48.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 150.0000 55 8 omega -10.00 69.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 -120.0000 79 9 omega 47.00 108.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 90.0000 61 10 omega 25.00 115.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 77.0000 120.0000 90 11 omega -11.00 73.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 -30.0000 84 12 omega 126.00 172.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 60.0000 46 13 omega 89.00 115.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 60.0000 26 14 omega 85.00 120.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 120.0000 35 15 omega 37.00 77.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 0.0000 40 16 omega 89.00 175.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -30.0000 86 17 omega 104.00 167.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 -60.0000 63 18 omega 114.00 174.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 30.0000 60 19 omega 77.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 30.0000 26 20 omega 36.00 85.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -150.0000 49 21 omega 58.00 108.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -30.0000 50 22 omega 94.00 171.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 90.0000 77 23 omega 65.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -180.0000 49 24 omega 77.00 165.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 0.0000 88 25 omega 41.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 60.0000 72 26 omega 77.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 60.0000 26 27 omega 39.00 64.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 -150.0000 25 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1306135000 _diffrn_orient_matrix_UB_12 0.0291155000 _diffrn_orient_matrix_UB_13 -0.0044052000 _diffrn_orient_matrix_UB_21 -0.0458776000 _diffrn_orient_matrix_UB_22 0.1520639000 _diffrn_orient_matrix_UB_23 -0.0587369000 _diffrn_orient_matrix_UB_31 0.0271951000 _diffrn_orient_matrix_UB_32 0.1164888000 _diffrn_orient_matrix_UB_33 0.0777882000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_unetI/netI 0.0328 _diffrn_reflns_laue_measured_fraction_full 0.982 _diffrn_reflns_laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8293 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.582 _diffrn_reflns_theta_min 4.155 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.859 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.389 _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.229 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2629 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0473 _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^)+(0.0798P)^2^+0.2912P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1290 _refine_ls_wR_factor_ref 0.1317 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2437 _reflns_number_total 2629 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ol5b01503_si_002.cif _cod_data_source_block q_4_10_2 _cod_database_code 1520708 _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. ; _reflns_odcompleteness_completeness 97.99 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C15(H15) 2.b Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' 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 0.58486(9) 1.02901(15) 0.10297(7) 0.0468(3) Uani 1 1 d . O2 O 0.54772(12) 0.97604(16) 0.27314(7) 0.0564(4) Uani 1 1 d . O3 O 0.53991(12) 0.51501(14) 0.10939(8) 0.0530(3) Uani 1 1 d . O4 O 0.09940(11) 0.97107(14) 0.19328(7) 0.0466(3) Uani 1 1 d . N1 N 0.38297(10) 1.03855(14) 0.09344(7) 0.0314(3) Uani 1 1 d . N12 N 0.56887(11) 0.72848(16) 0.20797(8) 0.0410(3) Uani 1 1 d . N14 N 0.40410(11) 0.73481(14) 0.09417(7) 0.0349(3) Uani 1 1 d . C2 C 0.39193(12) 0.88336(16) 0.14262(8) 0.0309(3) Uani 1 1 d . C3 C 0.28962(13) 0.87036(17) 0.18085(9) 0.0356(3) Uani 1 1 d . H3 H 0.2945 0.7884 0.2217 0.043 Uiso 1 1 calc R C4 C 0.19199(13) 0.97110(17) 0.15886(9) 0.0341(3) Uani 1 1 d . C5 C 0.17315(12) 1.09259(16) 0.08974(8) 0.0329(3) Uani 1 1 d . C6 C 0.06298(14) 1.1770(2) 0.05542(11) 0.0445(4) Uani 1 1 d . H6 H 0.0001 1.1634 0.0793 0.053 Uiso 1 1 calc R C7 C 0.04644(15) 1.2810(2) -0.01395(12) 0.0524(4) Uani 1 1 d . H7 H -0.0268 1.3393 -0.0359 0.063 Uiso 1 1 calc R C8 C 0.13818(16) 1.2982(2) -0.05060(11) 0.0499(4) Uani 1 1 d . H8 H 0.1260 1.3665 -0.0980 0.060 Uiso 1 1 calc R C9 C 0.24862(15) 1.21493(19) -0.01755(10) 0.0411(4) Uani 1 1 d . H9 H 0.3095 1.2249 -0.0435 0.049 Uiso 1 1 calc R C10 C 0.26797(12) 1.11627(16) 0.05461(8) 0.0311(3) Uani 1 1 d . C11 C 0.51394(13) 0.87532(19) 0.21645(9) 0.0384(3) Uani 1 1 d . C13 C 0.50570(13) 0.64534(18) 0.13273(9) 0.0359(3) Uani 1 1 d . C15 C 0.48766(13) 1.10233(19) 0.08243(9) 0.0372(3) Uani 1 1 d . H15 H 0.4840 1.2080 0.0578 0.045 Uiso 1 1 calc R C16 C 0.68576(18) 0.6724(3) 0.26478(13) 0.0652(5) Uani 1 1 d . H16A H 0.7297 0.7669 0.2955 0.098 Uiso 1 1 calc GR H16B H 0.7329 0.6215 0.2324 0.098 Uiso 1 1 calc GR H16C H 0.6720 0.5916 0.3039 0.098 Uiso 1 1 calc GR C17 C 0.31129(14) 0.6816(2) 0.01796(10) 0.0449(4) Uani 1 1 d . H17A H 0.2421 0.6381 0.0322 0.067 Uiso 1 1 calc GR H17B H 0.3440 0.5954 -0.0095 0.067 Uiso 1 1 calc GR H17C H 0.2861 0.7757 -0.0196 0.067 Uiso 1 1 calc GR C18 C 0.1031(2) 0.8454(3) 0.25533(14) 0.0635(5) Uani 1 1 d . H18A H 0.1105 0.7365 0.2324 0.095 Uiso 1 1 calc GR H18B H 0.0292 0.8501 0.2708 0.095 Uiso 1 1 calc GR H18C H 0.1722 0.8650 0.3045 0.095 Uiso 1 1 calc GR 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 0.0344(6) 0.0537(7) 0.0503(7) -0.0040(5) 0.0102(5) -0.0002(5) O2 0.0601(7) 0.0586(8) 0.0377(6) -0.0195(5) -0.0037(5) 0.0088(6) O3 0.0650(8) 0.0399(6) 0.0591(7) -0.0065(5) 0.0263(6) 0.0150(5) O4 0.0521(6) 0.0442(6) 0.0531(7) 0.0099(5) 0.0301(5) 0.0076(5) N1 0.0341(6) 0.0284(6) 0.0307(6) 0.0001(4) 0.0088(5) 0.0014(4) N12 0.0407(7) 0.0411(7) 0.0356(7) 0.0011(5) 0.0036(5) 0.0125(5) N14 0.0401(6) 0.0299(6) 0.0322(6) -0.0072(4) 0.0074(5) 0.0027(5) C2 0.0365(7) 0.0271(7) 0.0262(6) -0.0022(5) 0.0054(5) 0.0041(5) C3 0.0463(8) 0.0313(7) 0.0300(7) 0.0045(5) 0.0131(6) 0.0050(6) C4 0.0410(7) 0.0309(7) 0.0326(7) -0.0020(5) 0.0146(6) 0.0003(5) C5 0.0361(7) 0.0277(6) 0.0330(7) -0.0006(5) 0.0077(5) 0.0011(5) C6 0.0374(8) 0.0405(8) 0.0548(10) 0.0056(7) 0.0129(7) 0.0053(6) C7 0.0415(8) 0.0442(9) 0.0624(11) 0.0136(8) 0.0025(8) 0.0094(7) C8 0.0556(10) 0.0431(9) 0.0429(9) 0.0156(7) 0.0033(7) 0.0037(7) C9 0.0479(8) 0.0393(8) 0.0356(8) 0.0066(6) 0.0119(6) -0.0006(6) C10 0.0347(7) 0.0257(6) 0.0301(7) -0.0012(5) 0.0060(5) 0.0011(5) C11 0.0411(8) 0.0403(8) 0.0293(7) -0.0041(6) 0.0039(6) 0.0063(6) C13 0.0432(8) 0.0308(7) 0.0368(7) 0.0005(5) 0.0168(6) 0.0040(6) C15 0.0374(8) 0.0369(7) 0.0372(7) -0.0043(6) 0.0111(6) -0.0035(6) C16 0.0509(10) 0.0704(13) 0.0593(11) 0.0044(9) -0.0051(8) 0.0240(9) C17 0.0448(8) 0.0471(9) 0.0391(8) -0.0148(6) 0.0073(7) -0.0070(7) C18 0.0816(13) 0.0584(11) 0.0690(12) 0.0212(9) 0.0504(11) 0.0126(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C4 O4 C18 116.85(12) C10 N1 C2 121.03(11) C15 N1 C2 118.20(12) C15 N1 C10 120.69(12) C11 N12 C13 111.67(12) C11 N12 C16 124.33(14) C13 N12 C16 123.68(14) C13 N14 C2 112.41(11) C13 N14 C17 123.96(12) C17 N14 C2 123.36(12) N1 C2 C3 111.30(11) N1 C2 C11 111.45(11) N14 C2 N1 112.18(10) N14 C2 C3 113.38(11) N14 C2 C11 100.68(10) C3 C2 C11 107.28(11) C2 C3 H3 118.5 C4 C3 C2 122.96(12) C4 C3 H3 118.5 O4 C4 C5 112.63(12) C3 C4 O4 125.99(13) C3 C4 C5 121.34(12) C6 C5 C4 122.46(13) C6 C5 C10 119.45(13) C10 C5 C4 118.00(12) C5 C6 H6 119.8 C7 C6 C5 120.34(15) C7 C6 H6 119.8 C6 C7 H7 120.0 C8 C7 C6 120.00(15) C8 C7 H7 120.0 C7 C8 H8 119.7 C7 C8 C9 120.60(14) C9 C8 H8 119.7 C8 C9 H9 120.2 C8 C9 C10 119.68(14) C10 C9 H9 120.2 C5 C10 N1 119.15(12) C9 C10 N1 121.09(12) C9 C10 C5 119.77(13) O2 C11 N12 127.28(14) O2 C11 C2 125.74(13) N12 C11 C2 106.81(11) O3 C13 N12 123.90(14) O3 C13 N14 128.11(14) N14 C13 N12 107.99(12) O1 C15 N1 123.71(14) O1 C15 H15 118.1 N1 C15 H15 118.1 N12 C16 H16A 109.5 N12 C16 H16B 109.5 N12 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 N14 C17 H17A 109.5 N14 C17 H17B 109.5 N14 C17 H17C 109.5 H17A C17 H17B 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 O4 C18 H18A 109.5 O4 C18 H18B 109.5 O4 C18 H18C 109.5 H18A C18 H18B 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C15 1.2112(18) O2 C11 1.2051(18) O3 C13 1.2132(18) O4 C4 1.3520(17) O4 C18 1.426(2) N1 C2 1.4655(16) N1 C10 1.4200(17) N1 C15 1.3671(18) N12 C11 1.3548(19) N12 C13 1.4015(19) N12 C16 1.453(2) N14 C2 1.4594(16) N14 C13 1.3478(18) N14 C17 1.4437(18) C2 C3 1.4996(19) C2 C11 1.5527(19) C3 H3 0.9300 C3 C4 1.334(2) C4 C5 1.4637(19) C5 C6 1.389(2) C5 C10 1.3960(19) C6 H6 0.9300 C6 C7 1.382(2) C7 H7 0.9300 C7 C8 1.375(3) C8 H8 0.9300 C8 C9 1.385(2) C9 H9 0.9300 C9 C10 1.3908(19) C15 H15 0.9300 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 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 O4 C4 C5 C6 -9.7(2) O4 C4 C5 C10 173.83(12) N1 C2 C3 C4 11.87(19) N1 C2 C11 O2 59.1(2) N1 C2 C11 N12 -125.53(12) N14 C2 C3 C4 -115.73(15) N14 C2 C11 O2 178.19(16) N14 C2 C11 N12 -6.39(14) C2 N1 C10 C5 27.03(17) C2 N1 C10 C9 -152.91(13) C2 N1 C15 O1 8.3(2) C2 N14 C13 O3 178.49(14) C2 N14 C13 N12 -1.03(16) C2 C3 C4 O4 -176.94(13) C2 C3 C4 C5 5.5(2) C3 C2 C11 O2 -63.02(19) C3 C2 C11 N12 112.40(13) C3 C4 C5 C6 168.08(14) C3 C4 C5 C10 -8.3(2) C4 C5 C6 C7 -175.11(15) C4 C5 C10 N1 -7.64(18) C4 C5 C10 C9 172.31(13) C5 C6 C7 C8 1.5(3) C6 C5 C10 N1 175.82(13) C6 C5 C10 C9 -4.2(2) C6 C7 C8 C9 -1.4(3) C7 C8 C9 C10 -1.6(3) C8 C9 C10 N1 -175.65(14) C8 C9 C10 C5 4.4(2) C10 N1 C2 N14 100.23(13) C10 N1 C2 C3 -28.02(16) C10 N1 C2 C11 -147.74(11) C10 N1 C15 O1 -168.60(13) C10 C5 C6 C7 1.3(2) C11 N12 C13 O3 176.82(14) C11 N12 C13 N14 -3.63(17) C11 C2 C3 C4 134.03(14) C13 N12 C11 O2 -178.29(16) C13 N12 C11 C2 6.38(16) C13 N14 C2 N1 123.09(13) C13 N14 C2 C3 -109.78(13) C13 N14 C2 C11 4.48(14) C15 N1 C2 N14 -76.65(15) C15 N1 C2 C3 155.10(12) C15 N1 C2 C11 35.38(15) C15 N1 C10 C5 -156.16(12) C15 N1 C10 C9 23.89(19) C16 N12 C11 O2 -4.6(3) C16 N12 C11 C2 -179.90(16) C16 N12 C13 O3 3.1(2) C16 N12 C13 N14 -177.40(15) C17 N14 C2 N1 -62.71(17) C17 N14 C2 C3 64.42(17) C17 N14 C2 C11 178.68(13) C17 N14 C13 O3 4.3(2) C17 N14 C13 N12 -175.19(13) C18 O4 C4 C3 -3.8(2) C18 O4 C4 C5 173.87(15)