#------------------------------------------------------------------------------ #$Date: 2019-11-09 06:12:57 +0200 (Sat, 09 Nov 2019) $ #$Revision: 225409 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/90/7059030.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_7059030 loop_ _publ_author_name 'Camuenho, Ambr\'osio' 'Jorge Parola, A.' 'Alejo-Armijo, Alfonso' 'Pandian, Ramesh' 'Gomes, Clara S. B.' 'Laia, C\'esar A. T.' 'Pina, Fernando' _publ_section_title ; A model compound for pyridinechalcone-based multistate systems. Ring opening-closure as the slowest kinetic step of the multistate ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ04776J _journal_year 2019 _chemical_formula_moiety 'C18 H20 N2 O2' _chemical_formula_sum 'C18 H20 N2 O2' _chemical_formula_weight 296.36 _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 mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-05-31 deposited with the CCDC. 2019-10-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.953(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.0060(6) _cell_length_b 18.2400(17) _cell_length_c 12.5016(11) _cell_measurement_reflns_used 5050 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.31 _cell_measurement_theta_min 2.77 _cell_volume 1582.2(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick 2018)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1313 _diffrn_reflns_av_unetI/netI 0.0647 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 31778 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.680 _diffrn_reflns_theta_min 3.161 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.250 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 2992 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0668 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1542 _refine_ls_wR_factor_ref 0.1706 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1795 _reflns_number_total 2992 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj04776j2.cif _cod_data_source_block 7NPy4 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7059030 _shelx_shelxl_version_number 2018/3 _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 0.976 _shelx_estimated_absorpt_t_max 0.990 _shelx_res_file ; TITL mo_XS25_2016_17102016_Mo_0m_a.res in P2(1)/n shelx.res created by SHELXL-2018/3 at 11:24:54 on 02-May-2019 CELL 0.71073 7.0060 18.2400 12.5016 90.000 97.953 90.000 ZERR 4.00 0.0006 0.0017 0.0011 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 72 80 8 8 MERG 2 OMIT 0.00 180.00 OMIT 0 2 0 SHEL 8 0.82 FMAP 2 PLAN 20 SIZE 0.120 0.150 0.300 ACTA BOND $H CONF L.S. 4 TEMP 20.00 WGHT 0.088900 FVAR 0.66707 O2 4 0.126235 0.304673 0.482368 11.00000 0.03292 0.06037 = 0.03153 -0.00466 -0.00424 0.01141 O1 4 0.714199 0.162429 0.566175 11.00000 0.05042 0.06627 = 0.03816 -0.01317 -0.01524 0.01452 N2 3 -0.149956 0.444986 0.746507 11.00000 0.04638 0.05184 = 0.03770 -0.00513 0.00189 0.01319 N1 3 1.287337 0.150877 0.850783 11.00000 0.02789 0.05430 = 0.03445 0.00029 -0.00276 0.00518 C18 1 -0.268244 0.529713 0.598739 11.00000 0.08886 0.05325 = 0.08199 0.01571 0.00536 0.01560 AFIX 137 H18A 2 -0.221312 0.569870 0.644634 11.00000 -1.50000 H18B 2 -0.383065 0.544454 0.552783 11.00000 -1.50000 H18C 2 -0.171720 0.515619 0.555195 11.00000 -1.50000 AFIX 0 C17 1 -0.313341 0.465450 0.667414 11.00000 0.03805 0.05147 = 0.05809 0.00077 0.00516 0.01066 AFIX 23 H17A 2 -0.421522 0.477990 0.704637 11.00000 -1.20000 H17B 2 -0.350814 0.423790 0.620998 11.00000 -1.20000 AFIX 0 C12 1 -0.001951 0.403137 0.718991 11.00000 0.03413 0.03175 = 0.03346 0.00146 0.00297 -0.00014 C13 1 -0.007333 0.376101 0.613474 11.00000 0.02642 0.04033 = 0.02999 0.00391 -0.00322 0.00046 AFIX 43 H13 2 -0.110283 0.388600 0.561486 11.00000 -1.20000 AFIX 0 C14 1 0.136475 0.331418 0.585032 11.00000 0.02649 0.03579 = 0.02484 0.00245 0.00032 -0.00284 C9 1 0.296879 0.311769 0.659830 11.00000 0.02276 0.03441 = 0.03069 0.00682 -0.00364 -0.00371 C8 1 0.443476 0.263690 0.630223 11.00000 0.02546 0.03743 = 0.02844 0.00651 -0.00213 -0.00574 AFIX 43 H8 2 0.418549 0.242398 0.562127 11.00000 -1.20000 AFIX 0 C7 1 0.611932 0.245855 0.689050 11.00000 0.02608 0.04656 = 0.03417 -0.00136 -0.00376 -0.00017 AFIX 43 H7 2 0.643759 0.267587 0.756453 11.00000 -1.20000 AFIX 0 C6 1 0.745813 0.194707 0.652890 11.00000 0.02860 0.03604 = 0.02789 0.00377 -0.00079 -0.00299 C3 1 0.933067 0.179633 0.724731 11.00000 0.02233 0.03091 = 0.02498 0.00433 0.00134 -0.00340 C4 1 0.980981 0.210192 0.825389 11.00000 0.02917 0.04896 = 0.03375 -0.00485 -0.00030 0.00877 AFIX 43 H4 2 0.895098 0.241214 0.853560 11.00000 -1.20000 AFIX 0 C5 1 1.156943 0.194484 0.884014 11.00000 0.03682 0.06062 = 0.02805 -0.00755 -0.00728 0.00692 AFIX 43 H5 2 1.186209 0.216033 0.951717 11.00000 -1.20000 AFIX 0 C1 1 1.239271 0.120801 0.754083 11.00000 0.03473 0.05819 = 0.04165 -0.00945 -0.00048 0.01453 AFIX 43 H1 2 1.327219 0.089401 0.728462 11.00000 -1.20000 AFIX 0 C2 1 1.067386 0.133388 0.689833 11.00000 0.03534 0.05263 = 0.03172 -0.01046 -0.00048 0.00382 AFIX 43 H2 2 1.041423 0.110740 0.622748 11.00000 -1.20000 AFIX 0 C11 1 0.158012 0.383816 0.794346 11.00000 0.04197 0.04715 = 0.02762 -0.00694 -0.00274 -0.00225 AFIX 43 H11 2 0.167165 0.400849 0.864989 11.00000 -1.20000 AFIX 0 C10 1 0.299683 0.340328 0.764632 11.00000 0.02815 0.04710 = 0.03311 0.00226 -0.00923 -0.00096 AFIX 43 H10 2 0.403933 0.328879 0.816385 11.00000 -1.20000 AFIX 0 C15 1 -0.143596 0.478109 0.853322 11.00000 0.04744 0.05372 = 0.05588 -0.02218 0.00571 -0.00141 AFIX 23 H15B 2 -0.202119 0.526350 0.845441 11.00000 -1.20000 H15A 2 -0.010004 0.484408 0.884612 11.00000 -1.20000 AFIX 0 C16 1 -0.244922 0.433749 0.929339 11.00000 0.09972 0.12431 = 0.05067 -0.01488 0.01944 -0.04321 AFIX 137 H16C 2 -0.379121 0.429806 0.901158 11.00000 -1.50000 H16B 2 -0.231502 0.457383 0.998587 11.00000 -1.50000 H16A 2 -0.189015 0.385658 0.936940 11.00000 -1.50000 AFIX 0 H20 2 0.012249 0.321795 0.437707 11.00000 -1.50000 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM mo_XS25_2016_17102016_Mo_0m_a.res in P2(1)/n REM wR2 = 0.1706, GooF = S = 1.078, Restrained GooF = 1.078 for all data REM R1 = 0.0668 for 1795 Fo > 4sig(Fo) and 0.1293 for all 2992 data REM 204 parameters refined using 0 restraints END WGHT 0.0888 0.0000 REM Highest difference peak 0.250, deepest hole -0.276, 1-sigma level 0.053 Q1 1 0.3742 0.3149 0.8642 11.00000 0.05 0.25 Q2 1 -0.1294 0.5822 0.6792 11.00000 0.05 0.17 Q3 1 0.2555 0.3035 0.7181 11.00000 0.05 0.17 Q4 1 0.4447 0.2799 0.8003 11.00000 0.05 0.17 Q5 1 -0.0226 0.4581 0.7257 11.00000 0.05 0.17 Q6 1 0.0055 0.4144 0.6537 11.00000 0.05 0.17 Q7 1 -0.0406 0.3606 0.6768 11.00000 0.05 0.17 Q8 1 0.6841 0.2921 0.7343 11.00000 0.05 0.16 Q9 1 0.5616 0.2383 0.7709 11.00000 0.05 0.16 Q10 1 -0.2399 0.5782 0.6096 11.00000 0.05 0.16 Q11 1 1.0653 0.1902 0.9884 11.00000 0.05 0.16 Q12 1 1.5439 0.1332 0.7800 11.00000 0.05 0.15 Q13 1 -0.1295 0.3345 0.6872 11.00000 0.05 0.15 Q14 1 1.5013 0.0218 0.7593 11.00000 0.05 0.15 Q15 1 0.8858 0.1779 0.7923 11.00000 0.05 0.15 Q16 1 0.6756 0.2012 0.7332 11.00000 0.05 0.15 Q17 1 -0.3738 0.4024 0.9034 11.00000 0.05 0.15 Q18 1 -0.0082 0.3611 0.8226 11.00000 0.05 0.14 Q19 1 1.1458 0.1991 0.6435 11.00000 0.05 0.14 Q20 1 -0.6650 0.4886 0.7731 11.00000 0.05 0.14 ; _shelx_res_checksum 84211 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 O2 O 0.1262(2) 0.30467(10) 0.48237(14) 0.0424(5) Uani 1 1 d . . O1 O 0.7142(3) 0.16243(10) 0.56617(14) 0.0536(6) Uani 1 1 d . . N2 N -0.1500(3) 0.44499(12) 0.74651(16) 0.0457(6) Uani 1 1 d . . N1 N 1.2873(3) 0.15088(12) 0.85078(16) 0.0395(6) Uani 1 1 d . . C18 C -0.2682(5) 0.52971(17) 0.5987(3) 0.0753(11) Uani 1 1 d . . H18A H -0.221312 0.569870 0.644634 0.113 Uiso 1 1 calc R U H18B H -0.383065 0.544454 0.552783 0.113 Uiso 1 1 calc R U H18C H -0.171720 0.515619 0.555195 0.113 Uiso 1 1 calc R U C17 C -0.3133(4) 0.46545(15) 0.6674(2) 0.0493(7) Uani 1 1 d . . H17A H -0.421522 0.477990 0.704637 0.059 Uiso 1 1 calc R U H17B H -0.350814 0.423790 0.620998 0.059 Uiso 1 1 calc R U C12 C -0.0020(3) 0.40314(13) 0.71899(19) 0.0333(6) Uani 1 1 d . . C13 C -0.0073(3) 0.37610(13) 0.61347(18) 0.0329(6) Uani 1 1 d . . H13 H -0.110283 0.388600 0.561486 0.040 Uiso 1 1 calc R U C14 C 0.1365(3) 0.33142(12) 0.58503(18) 0.0293(6) Uani 1 1 d . . C9 C 0.2969(3) 0.31177(12) 0.65983(18) 0.0300(6) Uani 1 1 d . . C8 C 0.4435(3) 0.26369(13) 0.63022(18) 0.0310(6) Uani 1 1 d . . H8 H 0.418549 0.242398 0.562127 0.037 Uiso 1 1 calc R U C7 C 0.6119(3) 0.24586(13) 0.6891(2) 0.0363(6) Uani 1 1 d . . H7 H 0.643759 0.267587 0.756453 0.044 Uiso 1 1 calc R U C6 C 0.7458(3) 0.19471(13) 0.65289(18) 0.0313(6) Uani 1 1 d . . C3 C 0.9331(3) 0.17963(12) 0.72473(17) 0.0263(5) Uani 1 1 d . . C4 C 0.9810(3) 0.21019(14) 0.82539(19) 0.0377(6) Uani 1 1 d . . H4 H 0.895098 0.241214 0.853560 0.045 Uiso 1 1 calc R U C5 C 1.1569(4) 0.19448(15) 0.88401(19) 0.0429(7) Uani 1 1 d . . H5 H 1.186209 0.216033 0.951717 0.052 Uiso 1 1 calc R U C1 C 1.2393(4) 0.12080(15) 0.7541(2) 0.0454(7) Uani 1 1 d . . H1 H 1.327219 0.089401 0.728462 0.054 Uiso 1 1 calc R U C2 C 1.0674(3) 0.13339(14) 0.6898(2) 0.0404(7) Uani 1 1 d . . H2 H 1.041423 0.110740 0.622748 0.048 Uiso 1 1 calc R U C11 C 0.1580(4) 0.38382(13) 0.79435(19) 0.0396(7) Uani 1 1 d . . H11 H 0.167165 0.400849 0.864989 0.048 Uiso 1 1 calc R U C10 C 0.2997(3) 0.34033(13) 0.7646(2) 0.0374(6) Uani 1 1 d . . H10 H 0.403933 0.328879 0.816385 0.045 Uiso 1 1 calc R U C15 C -0.1436(4) 0.47811(15) 0.8533(2) 0.0525(8) Uani 1 1 d . . H15B H -0.202119 0.526350 0.845441 0.063 Uiso 1 1 calc R U H15A H -0.010004 0.484408 0.884612 0.063 Uiso 1 1 calc R U C16 C -0.2449(5) 0.4337(2) 0.9293(3) 0.0907(13) Uani 1 1 d . . H16C H -0.379121 0.429806 0.901158 0.136 Uiso 1 1 calc R U H16B H -0.231502 0.457383 0.998587 0.136 Uiso 1 1 calc R U H16A H -0.189015 0.385658 0.936940 0.136 Uiso 1 1 calc R U H20 H 0.012(6) 0.322(2) 0.438(3) 0.136 Uiso 1 1 d . 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 O2 0.0329(10) 0.0604(12) 0.0315(10) -0.0047(8) -0.0042(8) 0.0114(9) O1 0.0504(12) 0.0663(13) 0.0382(12) -0.0132(9) -0.0152(9) 0.0145(10) N2 0.0464(14) 0.0518(14) 0.0377(13) -0.0051(10) 0.0019(11) 0.0132(11) N1 0.0279(11) 0.0543(14) 0.0345(13) 0.0003(10) -0.0028(10) 0.0052(10) C18 0.089(3) 0.053(2) 0.082(3) 0.0157(17) 0.005(2) 0.0156(19) C17 0.0380(16) 0.0515(17) 0.0581(19) 0.0008(14) 0.0052(14) 0.0107(13) C12 0.0341(14) 0.0318(14) 0.0335(14) 0.0015(11) 0.0030(11) -0.0001(11) C13 0.0264(13) 0.0403(15) 0.0300(14) 0.0039(11) -0.0032(11) 0.0005(11) C14 0.0265(13) 0.0358(14) 0.0248(13) 0.0025(10) 0.0003(10) -0.0028(11) C9 0.0228(13) 0.0344(14) 0.0307(14) 0.0068(11) -0.0036(10) -0.0037(11) C8 0.0255(13) 0.0374(14) 0.0284(13) 0.0065(11) -0.0021(11) -0.0057(11) C7 0.0261(13) 0.0466(16) 0.0342(14) -0.0014(11) -0.0038(11) -0.0002(12) C6 0.0286(13) 0.0360(14) 0.0279(14) 0.0038(11) -0.0008(11) -0.0030(11) C3 0.0223(12) 0.0309(13) 0.0250(13) 0.0043(10) 0.0013(10) -0.0034(10) C4 0.0292(14) 0.0490(16) 0.0337(15) -0.0049(12) -0.0003(11) 0.0088(12) C5 0.0368(15) 0.0606(18) 0.0281(14) -0.0075(12) -0.0073(12) 0.0069(14) C1 0.0347(15) 0.0582(18) 0.0417(16) -0.0095(13) -0.0005(13) 0.0145(13) C2 0.0353(15) 0.0526(17) 0.0317(14) -0.0105(12) -0.0005(12) 0.0038(13) C11 0.0420(16) 0.0472(16) 0.0276(14) -0.0069(12) -0.0027(12) -0.0022(13) C10 0.0281(13) 0.0471(15) 0.0331(15) 0.0023(12) -0.0092(11) -0.0010(12) C15 0.0474(18) 0.0537(18) 0.0559(19) -0.0222(14) 0.0057(14) -0.0014(14) C16 0.100(3) 0.124(3) 0.051(2) -0.015(2) 0.019(2) -0.043(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C14 O2 H20 111(2) C12 N2 C17 121.6(2) C12 N2 C15 122.1(2) C17 N2 C15 115.9(2) C5 N1 C1 115.8(2) C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 N2 C17 C18 112.2(2) N2 C17 H17A 109.2 C18 C17 H17A 109.2 N2 C17 H17B 109.2 C18 C17 H17B 109.2 H17A C17 H17B 107.9 N2 C12 C13 120.6(2) N2 C12 C11 122.2(2) C13 C12 C11 117.2(2) C14 C13 C12 121.6(2) C14 C13 H13 119.2 C12 C13 H13 119.2 O2 C14 C13 120.5(2) O2 C14 C9 117.9(2) C13 C14 C9 121.6(2) C14 C9 C10 115.6(2) C14 C9 C8 121.2(2) C10 C9 C8 123.2(2) C7 C8 C9 127.8(2) C7 C8 H8 116.1 C9 C8 H8 116.1 C8 C7 C6 123.2(2) C8 C7 H7 118.4 C6 C7 H7 118.4 O1 C6 C7 122.9(2) O1 C6 C3 118.3(2) C7 C6 C3 118.8(2) C4 C3 C2 116.5(2) C4 C3 C6 123.6(2) C2 C3 C6 119.9(2) C5 C4 C3 119.4(2) C5 C4 H4 120.3 C3 C4 H4 120.3 N1 C5 C4 124.5(2) N1 C5 H5 117.8 C4 C5 H5 117.8 N1 C1 C2 123.8(2) N1 C1 H1 118.1 C2 C1 H1 118.1 C1 C2 C3 120.0(2) C1 C2 H2 120.0 C3 C2 H2 120.0 C10 C11 C12 120.5(2) C10 C11 H11 119.8 C12 C11 H11 119.8 C11 C10 C9 123.6(2) C11 C10 H10 118.2 C9 C10 H10 118.2 N2 C15 C16 113.5(2) N2 C15 H15B 108.9 C16 C15 H15B 108.9 N2 C15 H15A 108.9 C16 C15 H15A 108.9 H15B C15 H15A 107.7 C15 C16 H16C 109.5 C15 C16 H16B 109.5 H16C C16 H16B 109.5 C15 C16 H16A 109.5 H16C C16 H16A 109.5 H16B C16 H16A 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C14 1.366(3) O2 H20 0.96(4) O1 C6 1.227(3) N2 C12 1.369(3) N2 C17 1.454(3) N2 C15 1.461(3) N1 C5 1.321(3) N1 C1 1.328(3) C18 C17 1.512(4) C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 C17 H17A 0.9700 C17 H17B 0.9700 C12 C13 1.404(3) C12 C11 1.406(3) C13 C14 1.380(3) C13 H13 0.9300 C14 C9 1.405(3) C9 C10 1.408(3) C9 C8 1.437(3) C8 C7 1.341(3) C8 H8 0.9300 C7 C6 1.439(3) C7 H7 0.9300 C6 C3 1.509(3) C3 C4 1.375(3) C3 C2 1.379(3) C4 C5 1.374(3) C4 H4 0.9300 C5 H5 0.9300 C1 C2 1.371(3) C1 H1 0.9300 C2 H2 0.9300 C11 C10 1.362(3) C11 H11 0.9300 C10 H10 0.9300 C15 C16 1.499(4) C15 H15B 0.9700 C15 H15A 0.9700 C16 H16C 0.9600 C16 H16B 0.9600 C16 H16A 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 C12 N2 C17 C18 -80.2(3) C15 N2 C17 C18 93.5(3) C17 N2 C12 C13 -2.5(4) C15 N2 C12 C13 -175.8(2) C17 N2 C12 C11 179.1(2) C15 N2 C12 C11 5.8(4) N2 C12 C13 C14 -177.4(2) C11 C12 C13 C14 1.1(3) C12 C13 C14 O2 178.8(2) C12 C13 C14 C9 -1.1(3) O2 C14 C9 C10 -179.5(2) C13 C14 C9 C10 0.3(3) O2 C14 C9 C8 -1.4(3) C13 C14 C9 C8 178.4(2) C14 C9 C8 C7 173.1(2) C10 C9 C8 C7 -9.0(4) C9 C8 C7 C6 177.6(2) C8 C7 C6 O1 -1.4(4) C8 C7 C6 C3 178.9(2) O1 C6 C3 C4 -177.3(2) C7 C6 C3 C4 2.4(3) O1 C6 C3 C2 3.2(3) C7 C6 C3 C2 -177.1(2) C2 C3 C4 C5 1.0(3) C6 C3 C4 C5 -178.5(2) C1 N1 C5 C4 -0.5(4) C3 C4 C5 N1 -0.3(4) C5 N1 C1 C2 0.6(4) N1 C1 C2 C3 0.1(4) C4 C3 C2 C1 -0.9(3) C6 C3 C2 C1 178.7(2) N2 C12 C11 C10 178.1(2) C13 C12 C11 C10 -0.3(3) C12 C11 C10 C9 -0.4(4) C14 C9 C10 C11 0.5(4) C8 C9 C10 C11 -177.6(2) C12 N2 C15 C16 -96.5(3) C17 N2 C15 C16 89.9(3)