#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:21 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306586 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577400.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_1577400 loop_ _publ_author_name 'Hogan, David Thomas' 'Krappe, Alexander R.' 'Feyerherm, R.' 'Weber, Manuela' 'Resch-Genger, Ute' 'Eigler, Siegfried' _publ_section_title ; Large Stokes shift fluorophores from meta-substituted zwitterions ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03405E _journal_year 2026 _chemical_formula_sum 'C18 H14 N4' _chemical_formula_weight 286.33 _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' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-08 deposited with the CCDC. 2026-06-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.300(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.3190(10) _cell_length_b 13.967(2) _cell_length_c 11.3680(10) _cell_measurement_reflns_used 1955 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 66.47 _cell_measurement_theta_min 5.13 _cell_volume 1427.2(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX4' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type 'Bruker Photon CMOS Detector, D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_unetI/netI 0.0656 _diffrn_reflns_Laue_measured_fraction_full 0.966 _diffrn_reflns_Laue_measured_fraction_max 0.966 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6241 _diffrn_reflns_point_group_measured_fraction_full 0.966 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 65.082 _diffrn_reflns_theta_max 65.082 _diffrn_reflns_theta_min 3.164 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.333 _exptl_crystal_description platelet _exptl_crystal_F_000 600 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.040 _exptl_transmission_factor_max 0.8642 _exptl_transmission_factor_min 0.6027 _refine_diff_density_max 0.891 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.085 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2353 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.0948 _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^)+(0.1082P)^2^+4.2837P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2417 _refine_ls_wR_factor_ref 0.2616 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1738 _reflns_number_total 2353 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03405e2.cif _cod_data_source_block 0761DH _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1577400 _shelx_shelxl_version_number 2019/3 _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_min 0.903 _shelx_estimated_absorpt_t_max 0.974 _shelx_res_file ; TITL fast_a.res in P2(1)/n 0761DH.res created by SHELXL-2019/3 at 09:09:52 on 24-Jun-2025 REM Old TITL fast in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.173, Rweak 0.010, Alpha 0.042 REM 0.335 for 63 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N4 REM ##### CELL 1.54178 9.319 13.967 11.368 90 105.3 90 ZERR 4 0.001 0.002 0.001 0 0.01 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 72 56 16 L.S. 30 PLAN 5 SIZE 0.04 0.1 0.16 TEMP -123.15 CONF BOND $H htab LIST 4 MORE -1 fmap 2 acta SHEL 1000 0.85 TWIN -1 0 0 0 -1 0 0 0 1 2 OMIT 2 0 10 OMIT 3 0 9 WGHT 0.108200 4.283700 BASF 0.00456 FVAR 0.63210 N1 3 1.158679 0.638145 0.852800 11.00000 0.02504 0.03221 = 0.02760 0.00152 0.00265 0.00020 N2 3 1.238410 0.713575 0.718129 11.00000 0.03159 0.03238 = 0.02502 -0.00201 0.00579 -0.00143 N3 3 0.121652 0.619354 0.301977 11.00000 0.05004 0.05269 = 0.06154 -0.00423 0.02112 0.00194 N4 3 0.323193 0.432111 0.079621 11.00000 0.05209 0.05786 = 0.04449 -0.01371 0.00255 0.01088 C1 1 0.700769 0.686101 0.625904 11.00000 0.03563 0.04617 = 0.03618 -0.00501 0.01472 0.00493 AFIX 43 H1 2 0.618455 0.709881 0.651617 11.00000 -1.20000 AFIX 0 C2 1 0.677358 0.638139 0.515310 11.00000 0.04137 0.02515 = 0.04136 0.00363 0.01866 0.00383 C3 1 0.796575 0.607241 0.471002 11.00000 0.04918 0.02620 = 0.02723 0.00184 0.01823 0.00717 C4 1 0.946638 0.623198 0.546495 11.00000 0.04182 0.03135 = 0.03287 0.00348 0.00078 -0.00554 AFIX 43 H4 2 1.029741 0.603498 0.518865 11.00000 -1.20000 AFIX 0 C5 1 0.967817 0.666675 0.657458 11.00000 0.03461 0.02894 = 0.02938 0.00759 0.00024 -0.00139 C6 1 0.840648 0.698902 0.696858 11.00000 0.03388 0.04307 = 0.03634 0.00337 0.00739 0.00224 AFIX 43 H6 2 0.855571 0.729536 0.773759 11.00000 -1.20000 AFIX 0 C7 1 1.116440 0.673991 0.740374 11.00000 0.03022 0.02130 = 0.02806 -0.00076 0.00349 -0.00247 C8 1 1.308459 0.654050 0.902477 11.00000 0.03296 0.03466 = 0.02924 -0.00005 0.00081 -0.00302 AFIX 43 H8 2 1.365623 0.634781 0.981024 11.00000 -1.20000 AFIX 0 C9 1 1.358297 0.702132 0.818383 11.00000 0.02691 0.03780 = 0.03430 -0.00189 0.00365 -0.00156 AFIX 43 H9 2 1.457011 0.723946 0.826584 11.00000 -1.20000 AFIX 0 C10 1 0.528560 0.619476 0.439281 11.00000 0.03809 0.03938 = 0.03834 0.00076 0.01062 0.00325 AFIX 43 H10 2 0.445823 0.641478 0.465803 11.00000 -1.20000 AFIX 0 C11 1 0.503174 0.571978 0.332156 11.00000 0.04111 0.02434 = 0.03857 0.00504 0.00091 -0.00342 C12 1 0.630877 0.543867 0.289666 11.00000 0.03263 0.03734 = 0.03916 -0.00287 0.00513 -0.00037 AFIX 43 H12 2 0.615542 0.512935 0.212917 11.00000 -1.20000 AFIX 0 C13 1 0.773070 0.561115 0.358181 11.00000 0.03664 0.03792 = 0.04105 -0.00364 0.00859 0.00387 AFIX 43 H13 2 0.855415 0.541854 0.329258 11.00000 -1.20000 AFIX 0 C14 1 0.355337 0.549408 0.256334 11.00000 0.02235 0.03803 = 0.03426 0.00053 -0.00245 -0.00152 C15 1 0.225421 0.586317 0.281590 11.00000 0.03871 0.03310 = 0.03336 -0.00232 0.00410 -0.00502 C16 1 0.337647 0.485492 0.160231 11.00000 0.02236 0.03936 = 0.03750 0.00492 -0.00182 0.00506 C17 1 1.241382 0.768753 0.609332 11.00000 0.04839 0.05118 = 0.03377 0.00762 0.00912 -0.00955 AFIX 137 H17A 2 1.243098 0.724827 0.542494 11.00000 -1.50000 H17B 2 1.330518 0.809136 0.627054 11.00000 -1.50000 H17C 2 1.152519 0.809239 0.585607 11.00000 -1.50000 AFIX 0 C18 1 1.064278 0.584854 0.915118 11.00000 0.03564 0.05716 = 0.04349 0.01787 0.00312 -0.01310 AFIX 137 H18A 2 0.972704 0.564894 0.855467 11.00000 -1.50000 H18B 2 1.039281 0.625953 0.976726 11.00000 -1.50000 H18C 2 1.117882 0.528169 0.954726 11.00000 -1.50000 REM REM 0761DH.hkl REM AFIX 0 HKLF 4 REM fast_a.res in P2(1)/n REM wR2 = 0.2616, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0948 for 1738 Fo > 4sig(Fo) and 0.1209 for all 2353 data REM 202 parameters refined using 0 restraints END WGHT 0.1085 4.2741 REM Instructions for potential hydrogen bonds EQIV $1 -x+3/2, y+1/2, -z+1/2 HTAB C17 N4_$1 EQIV $2 x+1, y, z+1 HTAB C18 N4_$2 REM Highest difference peak 0.891, deepest hole -0.343, 1-sigma level 0.085 Q1 1 0.8944 0.5806 0.4327 11.00000 0.05 0.89 Q2 1 0.5657 0.6601 0.5651 11.00000 0.05 0.84 Q3 1 0.8581 0.6580 0.6304 11.00000 0.05 0.62 Q4 1 0.6178 0.5679 0.3720 11.00000 0.05 0.61 Q5 1 0.4552 0.5810 0.3808 11.00000 0.05 0.37 ; _shelx_res_checksum 32154 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.1587(4) 0.6381(3) 0.8528(3) 0.0291(9) Uani 1 1 d . . . . . N2 N 1.2384(4) 0.7136(3) 0.7181(3) 0.0300(9) Uani 1 1 d . . . . . N3 N 0.1217(5) 0.6194(3) 0.3020(4) 0.0535(12) Uani 1 1 d . . . . . N4 N 0.3232(5) 0.4321(4) 0.0796(4) 0.0534(13) Uani 1 1 d . . . . . C1 C 0.7008(5) 0.6861(4) 0.6259(4) 0.0383(12) Uani 1 1 d . . . . . H1 H 0.618455 0.709881 0.651617 0.046 Uiso 1 1 calc R U . . . C2 C 0.6774(5) 0.6381(3) 0.5153(4) 0.0345(11) Uani 1 1 d . . . . . C3 C 0.7966(5) 0.6072(3) 0.4710(4) 0.0327(11) Uani 1 1 d . . . . . C4 C 0.9466(5) 0.6232(3) 0.5465(4) 0.0371(11) Uani 1 1 d . . . . . H4 H 1.029741 0.603498 0.518865 0.044 Uiso 1 1 calc R U . . . C5 C 0.9678(5) 0.6667(3) 0.6575(4) 0.0325(11) Uani 1 1 d . . . . . C6 C 0.8406(5) 0.6989(4) 0.6969(4) 0.0381(11) Uani 1 1 d . . . . . H6 H 0.855571 0.729536 0.773759 0.046 Uiso 1 1 calc R U . . . C7 C 1.1164(5) 0.6740(3) 0.7404(4) 0.0273(10) Uani 1 1 d . . . . . C8 C 1.3085(5) 0.6541(3) 0.9025(4) 0.0337(11) Uani 1 1 d . . . . . H8 H 1.365623 0.634781 0.981024 0.040 Uiso 1 1 calc R U . . . C9 C 1.3583(5) 0.7021(3) 0.8184(4) 0.0338(11) Uani 1 1 d . . . . . H9 H 1.457011 0.723946 0.826584 0.041 Uiso 1 1 calc R U . . . C10 C 0.5286(5) 0.6195(3) 0.4393(4) 0.0385(11) Uani 1 1 d . . . . . H10 H 0.445823 0.641478 0.465803 0.046 Uiso 1 1 calc R U . . . C11 C 0.5032(5) 0.5720(3) 0.3322(4) 0.0365(11) Uani 1 1 d . . . . . C12 C 0.6309(5) 0.5439(3) 0.2897(4) 0.0372(11) Uani 1 1 d . . . . . H12 H 0.615542 0.512935 0.212917 0.045 Uiso 1 1 calc R U . . . C13 C 0.7731(5) 0.5611(3) 0.3582(4) 0.0389(12) Uani 1 1 d . . . . . H13 H 0.855415 0.541854 0.329258 0.047 Uiso 1 1 calc R U . . . C14 C 0.3553(5) 0.5494(3) 0.2563(4) 0.0334(11) Uani 1 1 d . . . . . C15 C 0.2254(6) 0.5863(3) 0.2816(4) 0.0361(11) Uani 1 1 d . . . . . C16 C 0.3376(5) 0.4855(3) 0.1602(4) 0.0349(11) Uani 1 1 d . . . . . C17 C 1.2414(6) 0.7688(4) 0.6093(4) 0.0448(13) Uani 1 1 d . . . . . H17A H 1.243098 0.724827 0.542494 0.067 Uiso 1 1 calc R U . . . H17B H 1.330518 0.809136 0.627054 0.067 Uiso 1 1 calc R U . . . H17C H 1.152519 0.809239 0.585607 0.067 Uiso 1 1 calc R U . . . C18 C 1.0643(6) 0.5849(4) 0.9151(5) 0.0468(14) Uani 1 1 d . . . . . H18A H 0.972704 0.564894 0.855467 0.070 Uiso 1 1 calc R U . . . H18B H 1.039281 0.625953 0.976726 0.070 Uiso 1 1 calc R U . . . H18C H 1.117882 0.528169 0.954726 0.070 Uiso 1 1 calc R U . . . 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 0.0250(19) 0.0322(19) 0.0276(19) 0.0015(15) 0.0027(15) 0.0002(15) N2 0.032(2) 0.032(2) 0.0250(19) -0.0020(15) 0.0058(16) -0.0014(16) N3 0.050(3) 0.053(3) 0.062(3) -0.004(2) 0.021(2) 0.002(2) N4 0.052(3) 0.058(3) 0.044(3) -0.014(2) 0.003(2) 0.011(2) C1 0.036(3) 0.046(3) 0.036(3) -0.005(2) 0.015(2) 0.005(2) C2 0.041(3) 0.025(2) 0.041(3) 0.0036(19) 0.019(2) 0.0038(19) C3 0.049(3) 0.026(2) 0.027(2) 0.0018(18) 0.018(2) 0.0072(19) C4 0.042(3) 0.031(2) 0.033(3) 0.003(2) 0.001(2) -0.006(2) C5 0.035(2) 0.029(2) 0.029(2) 0.0076(18) 0.0002(19) -0.0014(19) C6 0.034(3) 0.043(3) 0.036(3) 0.003(2) 0.007(2) 0.002(2) C7 0.030(2) 0.021(2) 0.028(2) -0.0008(16) 0.0035(18) -0.0025(17) C8 0.033(2) 0.035(2) 0.029(2) 0.0000(19) 0.0008(19) -0.0030(19) C9 0.027(2) 0.038(3) 0.034(3) -0.002(2) 0.0036(19) -0.0016(19) C10 0.038(3) 0.039(3) 0.038(3) 0.001(2) 0.011(2) 0.003(2) C11 0.041(3) 0.024(2) 0.039(3) 0.0050(19) 0.001(2) -0.0034(19) C12 0.033(3) 0.037(3) 0.039(3) -0.003(2) 0.005(2) 0.000(2) C13 0.037(3) 0.038(3) 0.041(3) -0.004(2) 0.009(2) 0.004(2) C14 0.022(2) 0.038(3) 0.034(2) 0.001(2) -0.0024(19) -0.0015(19) C15 0.039(3) 0.033(2) 0.033(3) -0.002(2) 0.004(2) -0.005(2) C16 0.022(2) 0.039(3) 0.038(3) 0.005(2) -0.0018(19) 0.0051(19) C17 0.048(3) 0.051(3) 0.034(3) 0.008(2) 0.009(2) -0.010(2) C18 0.036(3) 0.057(3) 0.043(3) 0.018(2) 0.003(2) -0.013(2) 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' 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 C7 N1 C8 110.1(4) . . ? C7 N1 C18 126.2(4) . . ? C8 N1 C18 123.7(4) . . ? C7 N2 C9 109.7(4) . . ? C7 N2 C17 125.4(4) . . ? C9 N2 C17 124.6(4) . . ? C6 C1 C2 120.0(5) . . ? C6 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 121.5(5) . . ? C1 C2 C10 121.5(4) . . ? C3 C2 C10 117.0(4) . . ? C13 C3 C2 121.5(5) . . ? C13 C3 C4 120.4(4) . . ? C2 C3 C4 118.1(4) . . ? C5 C4 C3 119.7(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 C7 120.6(4) . . ? C6 C5 C7 119.6(4) . . ? C1 C6 C5 121.0(4) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N1 C7 N2 106.5(4) . . ? N1 C7 C5 125.7(4) . . ? N2 C7 C5 127.7(4) . . ? C9 C8 N1 106.9(4) . . ? C9 C8 H8 126.5 . . ? N1 C8 H8 126.5 . . ? C8 C9 N2 106.8(4) . . ? C8 C9 H9 126.6 . . ? N2 C9 H9 126.6 . . ? C11 C10 C2 122.5(4) . . ? C11 C10 H10 118.7 . . ? C2 C10 H10 118.7 . . ? C10 C11 C12 117.9(4) . . ? C10 C11 C14 123.6(5) . . ? C12 C11 C14 118.4(4) . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C3 119.7(5) . . ? C12 C13 H13 120.1 . . ? C3 C13 H13 120.1 . . ? C16 C14 C15 117.7(4) . . ? C16 C14 C11 120.2(4) . . ? C15 C14 C11 121.9(4) . . ? N3 C15 C14 177.7(5) . . ? N4 C16 C14 179.8(6) . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 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 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.332(5) . ? N1 C8 1.379(6) . ? N1 C18 1.469(6) . ? N2 C7 1.347(6) . ? N2 C9 1.379(6) . ? N2 C17 1.464(6) . ? N3 C15 1.149(6) . ? N4 C16 1.161(6) . ? C1 C6 1.352(7) . ? C1 C2 1.390(7) . ? C1 H1 0.9500 . ? C2 C3 1.403(6) . ? C2 C10 1.451(7) . ? C3 C13 1.400(6) . ? C3 C4 1.452(7) . ? C4 C5 1.367(7) . ? C4 H4 0.9500 . ? C5 C6 1.445(7) . ? C5 C7 1.459(6) . ? C6 H6 0.9500 . ? C8 C9 1.347(6) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.352(7) . ? C10 H10 0.9500 . ? C11 C12 1.452(7) . ? C11 C14 1.454(6) . ? C12 C13 1.370(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C16 1.387(7) . ? C14 C15 1.413(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C6 C1 C2 C3 -4.0(7) . . . . ? C6 C1 C2 C10 177.3(5) . . . . ? C1 C2 C3 C13 -178.3(4) . . . . ? C10 C2 C3 C13 0.4(6) . . . . ? C1 C2 C3 C4 2.5(6) . . . . ? C10 C2 C3 C4 -178.7(4) . . . . ? C13 C3 C4 C5 -178.7(4) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C3 C4 C5 C6 -1.9(6) . . . . ? C3 C4 C5 C7 173.3(4) . . . . ? C2 C1 C6 C5 2.4(7) . . . . ? C4 C5 C6 C1 0.5(7) . . . . ? C7 C5 C6 C1 -174.7(4) . . . . ? C8 N1 C7 N2 -0.5(5) . . . . ? C18 N1 C7 N2 -177.6(4) . . . . ? C8 N1 C7 C5 176.9(4) . . . . ? C18 N1 C7 C5 -0.2(7) . . . . ? C9 N2 C7 N1 0.0(5) . . . . ? C17 N2 C7 N1 -174.4(4) . . . . ? C9 N2 C7 C5 -177.3(4) . . . . ? C17 N2 C7 C5 8.3(7) . . . . ? C4 C5 C7 N1 -120.6(5) . . . . ? C6 C5 C7 N1 54.5(6) . . . . ? C4 C5 C7 N2 56.2(6) . . . . ? C6 C5 C7 N2 -128.7(5) . . . . ? C7 N1 C8 C9 0.8(5) . . . . ? C18 N1 C8 C9 178.0(4) . . . . ? N1 C8 C9 N2 -0.8(5) . . . . ? C7 N2 C9 C8 0.5(5) . . . . ? C17 N2 C9 C8 175.0(4) . . . . ? C1 C2 C10 C11 -179.2(4) . . . . ? C3 C2 C10 C11 2.0(7) . . . . ? C2 C10 C11 C12 -3.6(7) . . . . ? C2 C10 C11 C14 177.8(4) . . . . ? C10 C11 C12 C13 2.8(7) . . . . ? C14 C11 C12 C13 -178.5(4) . . . . ? C11 C12 C13 C3 -0.4(7) . . . . ? C2 C3 C13 C12 -1.2(7) . . . . ? C4 C3 C13 C12 178.0(4) . . . . ? C10 C11 C14 C16 -167.8(5) . . . . ? C12 C11 C14 C16 13.5(7) . . . . ? C10 C11 C14 C15 8.2(7) . . . . ? C12 C11 C14 C15 -170.4(4) . . . . ?