#------------------------------------------------------------------------------ #$Date: 2016-02-20 16:35:30 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/42/2214299.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_2214299 loop_ _publ_author_name 'Zhu, Yu-Lan' 'Zhong, Zhi-Feng' 'Yin, Qi-Fan' 'Liu, Wei' _publ_section_title ; 3-(8-Methoxyquinolin-2-ylmethyl)-1-methyl-3H-1-imidazolium hexafluorophosphate ; _journal_coeditor_code LH2402 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3231 _journal_page_last o3231 _journal_paper_doi 10.1107/S1600536807026955 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C15 H17 N3 O + , F6 P -' _chemical_formula_moiety 'C15 H17 N3 O + , F6 P -' _chemical_formula_sum 'C15 H17 F6 N3 O P' _chemical_formula_weight 400.29 _chemical_name_systematic ; 3-(8-Methoxyquinolin-2-ylmethyl)-1-methyl-3H-1-imidazolium hexafluorophosphate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 112.0590(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 12.2183(11) _cell_length_b 21.3444(19) _cell_length_c 14.4056(13) _cell_measurement_temperature 291(2) _cell_volume 3481.9(5) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXTL (Bruker, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.1080 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12564 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_T_max 0.9644 _exptl_absorpt_correction_T_min 0.9473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1640 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 1.125 _refine_diff_density_min -0.674 _refine_ls_extinction_coef 0.0026(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 293 _refine_ls_number_reflns 3087 _refine_ls_number_restraints 108 _refine_ls_restrained_S_all 1.115 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0585 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0848P)^2^+6.8821P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1655 _refine_ls_wR_factor_ref 0.1697 _reflns_number_gt 2808 _reflns_number_total 3087 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh2402.cif _cod_data_source_block I _cod_original_sg_symbol_H-M C2/c _cod_database_code 2214299 _cod_database_fobs_code 2214299 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.01910(7) 0.33923(4) 0.99358(6) 0.0431(3) Uani d D 1 . . F F1 0.0575(5) 0.3561(2) 1.1098(3) 0.092(2) Uani d PDU 0.859(6) A 1 F F2 0.0141(3) 0.26827(11) 1.0220(2) 0.0687(9) Uani d PDU 0.859(6) A 1 F F3 -0.1135(2) 0.3483(2) 0.9796(3) 0.0951(13) Uani d PDU 0.859(6) A 1 F F4 0.0294(4) 0.41165(15) 0.9733(3) 0.1144(16) Uani d PDU 0.859(6) A 1 F F5 0.1552(2) 0.33103(19) 1.0130(3) 0.0916(12) Uani d PDU 0.859(6) A 1 F F6 -0.0185(5) 0.3223(3) 0.8809(3) 0.118(3) Uani d PDU 0.859(6) A 1 F F1' 0.0459(14) 0.3516(7) 1.1049(6) 0.038(6) Uani d PDU 0.141(6) A 2 F F2' -0.0984(11) 0.3001(8) 0.9825(10) 0.080(6) Uani d PDU 0.141(6) A 2 F F3' -0.0593(16) 0.3991(6) 0.9584(11) 0.089(7) Uani d PDU 0.141(6) A 2 F F4' 0.1291(12) 0.3739(9) 0.9927(12) 0.113(9) Uani d PDU 0.141(6) A 2 F F5' 0.0894(16) 0.2751(6) 1.0179(12) 0.117(9) Uani d PDU 0.141(6) A 2 F F6' -0.0142(12) 0.3222(7) 0.8752(7) 0.046(6) Uani d PDU 0.141(6) A 2 N N1 0.35973(18) 0.67281(10) 0.14547(16) 0.0286(5) Uani d . 1 . . N N2 0.51217(19) 0.55385(10) 0.12278(15) 0.0297(5) Uani d . 1 . . H H2 0.5699 0.5799 0.1455 0.036 Uiso calc R 1 . . N N3 0.29978(19) 0.68579(10) 0.26701(16) 0.0324(5) Uani d . 1 . . O O1 0.73297(16) 0.51432(9) 0.21731(16) 0.0406(5) Uani d . 1 . . C C1 0.5310(2) 0.49095(12) 0.13432(18) 0.0302(6) Uani d . 1 . . C C2 0.4026(2) 0.57384(13) 0.07571(19) 0.0326(6) Uani d . 1 . . C C3 0.3228(2) 0.64369(12) 0.20928(19) 0.0305(6) Uani d . 1 . . H H3 0.3143 0.6006 0.2130 0.037 Uiso calc R 1 . . C C4 0.3047(2) 0.53339(14) 0.0384(2) 0.0403(7) Uani d . 1 . . H H4 0.2290 0.5494 0.0063 0.048 Uiso calc R 1 . . C C5 0.6489(2) 0.46864(12) 0.1842(2) 0.0336(6) Uani d . 1 . . C C6 0.3226(3) 0.47019(14) 0.0499(2) 0.0407(7) Uani d . 1 . . H H6 0.2588 0.4429 0.0260 0.049 Uiso calc R 1 . . C C7 0.4631(3) 0.38144(13) 0.1118(2) 0.0410(7) Uani d . 1 . . H H7 0.4025 0.3522 0.0882 0.049 Uiso calc R 1 . . C C8 0.4378(2) 0.44646(13) 0.09821(19) 0.0338(6) Uani d . 1 . . C C9 0.3866(3) 0.64389(13) 0.0633(2) 0.0360(6) Uani d . 1 . . H H9A 0.4582 0.6624 0.0612 0.043 Uiso calc R 1 . . H H9B 0.3229 0.6528 0.0000 0.043 Uiso calc R 1 . . C C10 0.3589(3) 0.73643(13) 0.1622(2) 0.0385(6) Uani d . 1 . . H H10 0.3799 0.7680 0.1275 0.046 Uiso calc R 1 . . C C11 0.6706(3) 0.40540(13) 0.1961(2) 0.0407(7) Uani d . 1 . . H H11 0.7475 0.3910 0.2284 0.049 Uiso calc R 1 . . C C12 0.3219(3) 0.74401(13) 0.2382(2) 0.0401(7) Uani d . 1 . . H H12 0.3130 0.7820 0.2663 0.048 Uiso calc R 1 . . C C13 0.5766(3) 0.36226(13) 0.1594(2) 0.0436(7) Uani d . 1 . . H H13 0.5927 0.3196 0.1680 0.052 Uiso calc R 1 . . C C14 0.2529(3) 0.67183(15) 0.3445(2) 0.0460(7) Uani d . 1 . . H H14A 0.1684 0.6752 0.3166 0.069 Uiso calc R 1 . . H H14B 0.2846 0.7011 0.3987 0.069 Uiso calc R 1 . . H H14C 0.2750 0.6300 0.3690 0.069 Uiso calc R 1 . . C C15 0.8535(3) 0.49475(17) 0.2664(3) 0.0613(10) Uani d . 1 . . H H15A 0.8622 0.4725 0.3266 0.092 Uiso calc R 1 . . H H15B 0.9040 0.5309 0.2827 0.092 Uiso calc R 1 . . H H15C 0.8749 0.4678 0.2226 0.092 Uiso calc R 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 P1 0.0324(5) 0.0473(5) 0.0488(5) -0.0030(3) 0.0140(3) 0.0112(3) F1 0.112(4) 0.076(3) 0.066(3) 0.004(3) 0.009(2) -0.017(2) F2 0.092(2) 0.0408(13) 0.0805(18) -0.0165(13) 0.0406(16) -0.0023(12) F3 0.0347(14) 0.126(3) 0.115(3) 0.0141(16) 0.0167(14) -0.015(2) F4 0.113(3) 0.068(2) 0.128(3) -0.0150(19) 0.006(2) 0.0528(19) F5 0.0423(15) 0.118(3) 0.122(3) -0.0103(16) 0.0385(16) 0.007(2) F6 0.125(5) 0.168(5) 0.057(3) -0.007(4) 0.029(3) 0.003(3) F1' 0.047(8) 0.035(9) 0.034(9) 0.004(6) 0.019(7) 0.015(7) F2' 0.082(10) 0.101(11) 0.067(8) -0.024(8) 0.039(7) 0.009(7) F3' 0.102(11) 0.073(9) 0.094(10) 0.033(8) 0.039(8) 0.015(7) F4' 0.100(12) 0.111(12) 0.134(13) -0.018(9) 0.052(9) 0.002(9) F5' 0.114(12) 0.101(12) 0.116(12) 0.033(9) 0.021(9) -0.005(9) F6' 0.037(8) 0.083(11) 0.033(9) -0.009(7) 0.032(7) 0.002(7) N1 0.0253(10) 0.0285(11) 0.0319(11) 0.0030(8) 0.0105(8) 0.0018(8) N2 0.0319(11) 0.0288(11) 0.0321(11) -0.0008(9) 0.0165(9) -0.0039(9) N3 0.0322(11) 0.0332(11) 0.0325(11) 0.0028(9) 0.0130(9) -0.0019(9) O1 0.0328(10) 0.0339(10) 0.0514(12) 0.0035(8) 0.0113(9) -0.0043(9) C1 0.0380(14) 0.0310(13) 0.0274(12) 0.0017(10) 0.0190(11) -0.0021(10) C2 0.0354(13) 0.0364(14) 0.0305(13) 0.0051(11) 0.0174(11) -0.0016(11) C3 0.0335(13) 0.0269(12) 0.0314(13) 0.0033(10) 0.0124(10) 0.0017(10) C4 0.0318(14) 0.0500(17) 0.0410(15) 0.0025(12) 0.0159(12) -0.0058(13) C5 0.0377(14) 0.0323(14) 0.0337(13) 0.0018(11) 0.0166(11) -0.0033(10) C6 0.0378(15) 0.0461(17) 0.0433(15) -0.0078(12) 0.0210(12) -0.0107(13) C7 0.0544(18) 0.0345(14) 0.0419(15) -0.0075(12) 0.0270(14) -0.0057(12) C8 0.0418(14) 0.0340(14) 0.0323(13) -0.0042(11) 0.0215(11) -0.0052(11) C9 0.0391(14) 0.0381(15) 0.0357(14) 0.0082(11) 0.0195(12) 0.0039(11) C10 0.0421(15) 0.0278(13) 0.0478(16) -0.0030(11) 0.0193(13) 0.0012(12) C11 0.0483(16) 0.0335(14) 0.0420(15) 0.0088(12) 0.0190(13) 0.0016(12) C12 0.0465(16) 0.0276(13) 0.0471(16) 0.0012(11) 0.0183(13) -0.0052(12) C13 0.0627(19) 0.0275(13) 0.0463(16) 0.0018(13) 0.0271(15) 0.0005(12) C14 0.0552(18) 0.0516(18) 0.0409(16) 0.0011(14) 0.0290(14) -0.0024(13) C15 0.0341(16) 0.051(2) 0.084(3) 0.0072(14) 0.0059(16) -0.0075(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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_publ_flag F1' P1 F4' 94.7(6) ? F1' P1 F6 174.1(6) ? F4' P1 F6 91.2(7) ? F1' P1 F3' 93.6(5) ? F4' P1 F3' 92.0(6) ? F6 P1 F3' 87.0(7) ? F1' P1 F3 85.3(6) ? F4' P1 F3 143.4(8) ? F6 P1 F3 90.5(2) ? F3' P1 F3 51.7(7) ? F1' P1 F2 84.7(6) ? F4' P1 F2 125.7(8) ? F6 P1 F2 91.3(2) ? F3' P1 F2 142.3(7) ? F3 P1 F2 90.74(19) ? F1' P1 F5' 91.8(5) ? F4' P1 F5' 90.9(6) ? F6 P1 F5' 87.3(7) ? F3' P1 F5' 173.7(7) ? F3 P1 F5' 125.7(8) ? F1' P1 F4 91.4(6) ? F4' P1 F4 53.1(8) ? F6 P1 F4 92.7(3) ? F3 P1 F4 90.3(2) ? F2 P1 F4 175.85(18) ? F5' P1 F4 144.0(8) ? F1' P1 F5 92.1(6) ? F6 P1 F5 92.2(2) ? F3' P1 F5 128.4(7) ? F3 P1 F5 177.34(19) ? F2 P1 F5 89.34(17) ? F5' P1 F5 54.7(8) ? F4 P1 F5 89.4(2) ? F4' P1 F1 89.2(7) ? F6 P1 F1 179.5(3) ? F3' P1 F1 93.3(6) ? F3 P1 F1 89.4(2) ? F2 P1 F1 88.2(2) ? F5' P1 F1 92.4(7) ? F4 P1 F1 87.8(2) ? F5 P1 F1 88.0(2) ? F1' P1 F2' 91.4(5) ? F4' P1 F2' 173.8(6) ? F6 P1 F2' 82.7(6) ? F3' P1 F2' 88.6(5) ? F2 P1 F2' 53.8(7) ? F5' P1 F2' 87.9(5) ? F4 P1 F2' 127.9(7) ? F5 P1 F2' 142.5(7) ? F1 P1 F2' 96.9(6) ? F1' P1 F6' 176.4(6) ? F4' P1 F6' 88.6(5) ? F3' P1 F6' 87.8(5) ? F3 P1 F6' 93.0(5) ? F2 P1 F6' 92.2(6) ? F5' P1 F6' 86.6(5) ? F4 P1 F6' 91.8(6) ? F5 P1 F6' 89.6(5) ? F1 P1 F6' 177.5(6) ? F2' P1 F6' 85.3(5) ? C3 N1 C10 108.4(2) n C3 N1 C9 126.7(2) n C10 N1 C9 124.7(2) n C2 N2 C1 118.2(2) n C2 N2 H2 120.9 ? C1 N2 H2 120.9 ? C3 N3 C12 108.3(2) n C3 N3 C14 125.2(2) n C12 N3 C14 126.5(2) n C5 O1 C15 117.5(2) ? N2 C1 C8 122.6(2) n N2 C1 C5 118.8(2) n C8 C1 C5 118.6(2) ? N2 C2 C4 123.3(3) n N2 C2 C9 116.2(2) ? C4 C2 C9 120.5(2) ? N1 C3 N3 109.0(2) n N1 C3 H3 125.5 ? N3 C3 H3 125.5 ? C6 C4 C2 118.9(3) ? C6 C4 H4 120.5 ? C2 C4 H4 120.5 ? O1 C5 C11 125.0(3) ? O1 C5 C1 114.9(2) ? C11 C5 C1 120.1(3) ? C4 C6 C8 120.0(3) ? C4 C6 H6 120.0 ? C8 C6 H6 120.0 ? C13 C7 C8 119.5(3) ? C13 C7 H7 120.2 ? C8 C7 H7 120.2 ? C6 C8 C7 123.0(3) ? C6 C8 C1 117.0(3) ? C7 C8 C1 119.9(3) ? N1 C9 C2 112.1(2) n N1 C9 H9A 109.2 ? C2 C9 H9A 109.2 ? N1 C9 H9B 109.2 ? C2 C9 H9B 109.2 ? H9A C9 H9B 107.9 ? C12 C10 N1 106.7(2) n C12 C10 H10 126.6 ? N1 C10 H10 126.6 ? C5 C11 C13 120.2(3) ? C5 C11 H11 119.9 ? C13 C11 H11 119.9 ? C10 C12 N3 107.6(2) n C10 C12 H12 126.2 ? N3 C12 H12 126.2 ? C7 C13 C11 121.7(3) ? C7 C13 H13 119.2 ? C11 C13 H13 119.2 ? N3 C14 H14A 109.5 ? N3 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? N3 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? O1 C15 H15A 109.5 ? O1 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O1 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P1 F1' 1.534(8) ? P1 F4' 1.539(8) ? P1 F6 1.555(4) n P1 F3' 1.563(8) ? P1 F3 1.568(3) n P1 F2 1.576(2) n P1 F5' 1.584(8) ? P1 F4 1.587(3) n P1 F5 1.589(3) n P1 F1 1.601(4) n P1 F2' 1.616(8) ? P1 F6' 1.639(8) ? N1 C3 1.322(3) ? N1 C10 1.380(3) ? N1 C9 1.478(3) ? N2 C2 1.323(3) ? N2 C1 1.362(3) ? N2 H2 0.8600 ? N3 C3 1.324(3) ? N3 C12 1.369(4) ? N3 C14 1.464(3) ? O1 C5 1.366(3) ? O1 C15 1.436(4) ? C1 C8 1.423(4) ? C1 C5 1.429(4) ? C2 C4 1.409(4) ? C2 C9 1.510(4) ? C3 H3 0.9300 ? C4 C6 1.367(4) ? C4 H4 0.9300 ? C5 C11 1.374(4) ? C6 C8 1.409(4) ? C6 H6 0.9300 ? C7 C13 1.358(5) ? C7 C8 1.420(4) ? C7 H7 0.9300 ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C10 C12 1.343(4) ? C10 H10 0.9300 ? C11 C13 1.411(4) ? C11 H11 0.9300 ? C12 H12 0.9300 ? C13 H13 0.9300 ? C14 H14A 0.9600 ? C14 H14B 0.9600 ? C14 H14C 0.9600 ? C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 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 C12 H12 F1 4_556 0.93 2.46 3.204(5) 137 C9 H9A F2 3_554 0.97 2.49 3.244(4) 135 C3 H3 O1 2_655 0.93 2.27 3.122(3) 152 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 C2 N2 C1 C8 -0.2(3) C2 N2 C1 C5 179.5(2) C1 N2 C2 C4 0.9(4) C1 N2 C2 C9 -179.0(2) C10 N1 C3 N3 -0.8(3) C9 N1 C3 N3 -175.3(2) C12 N3 C3 N1 0.6(3) C14 N3 C3 N1 177.7(2) N2 C2 C4 C6 -0.7(4) C9 C2 C4 C6 179.3(2) C15 O1 C5 C11 1.4(4) C15 O1 C5 C1 -178.8(3) N2 C1 C5 O1 0.8(3) C8 C1 C5 O1 -179.4(2) N2 C1 C5 C11 -179.4(2) C8 C1 C5 C11 0.3(4) C2 C4 C6 C8 -0.3(4) C4 C6 C8 C7 -179.2(3) C4 C6 C8 C1 0.9(4) C13 C7 C8 C6 -179.8(3) C13 C7 C8 C1 0.1(4) N2 C1 C8 C6 -0.7(4) C5 C1 C8 C6 179.6(2) N2 C1 C8 C7 179.4(2) C5 C1 C8 C7 -0.2(4) C3 N1 C9 C2 -16.9(4) C10 N1 C9 C2 169.4(2) N2 C2 C9 N1 -93.1(3) C4 C2 C9 N1 87.0(3) C3 N1 C10 C12 0.7(3) C9 N1 C10 C12 175.4(2) O1 C5 C11 C13 179.5(2) C1 C5 C11 C13 -0.2(4) N1 C10 C12 N3 -0.4(3) C3 N3 C12 C10 -0.1(3) C14 N3 C12 C10 -177.2(3) C8 C7 C13 C11 0.1(4) C5 C11 C13 C7 0.0(4)