#------------------------------------------------------------------------------ #$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301775 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/16/1501653.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_1501653 loop_ _publ_author_name 'Jacquemin, Denis' 'Br\'emond, Eric' 'Planchat, Aur\'elien' 'Ciofini, Ilaria' 'Adamo, Carlo' _publ_section_title ; TD-DFT Vibronic Couplings in Anthraquinones: From Basis Set and Functional Benchmarks to Applications for Industrial Dyes ; _journal_issue 6 _journal_name_full 'Journal of Chemical Theory and Computation' _journal_page_first 1882 _journal_paper_doi 10.1021/ct200259k _journal_volume 7 _journal_year 2011 _chemical_formula_moiety 'C14 H10 N2 O2' _chemical_formula_sum 'C14 H10 N2 O2' _chemical_formula_weight 238.2 _chemical_name_systematic 1,4-diaminoanthraquinone _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 97.983(9) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.0342(10) _cell_length_b 12.2529(12) _cell_length_c 13.7875(11) _cell_measurement_temperature 293 _cell_volume 2180.6(3) _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _diffrn_measurement_device 'four-cycle diffractometer' _diffrn_measurement_device_type 'Nonius CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0958 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 38754 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 6.61 _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_correction_T_min 0.9772 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'Jana2006 (Petricek, Dusek & Palatinus, 2000)' _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.4509 _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.49 _refine_diff_density_min -0.34 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_gt 2.02 _refine_ls_goodness_of_fit_ref 1.93 _refine_ls_hydrogen_treatment mixed _refine_ls_number_constraints 24 _refine_ls_number_parameters 179 _refine_ls_number_reflns 2469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0741 _refine_ls_shift/su_max 0.0033 _refine_ls_shift/su_mean 0.0004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details w=1/(\s^2^(I)+0.001936I^2^) _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.1350 _refine_ls_wR_factor_ref 0.1665 _reflns_number_gt 1549 _reflns_number_total 2469 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ct200259k_si_002.cif _cod_data_source_block I _cod_database_code 1501653 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z+1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 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_adp_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity _atom_site_occupancy _atom_site_calc_flag O1 O -0.00025(10) 0.78220(16) -0.05846(12) Uani 0.0572(7) 8 1 d O2 O 0.36021(9) 0.94035(14) 0.12968(11) Uani 0.0486(6) 8 1 d N1 N 0.00432(18) 0.6199(3) 0.0624(2) Uani 0.0676(10) 8 1 d N2 N 0.37483(16) 0.7802(2) 0.25420(19) Uani 0.0569(9) 8 1 d C1 C 0.09311(16) 0.6645(2) 0.10686(18) Uani 0.0455(8) 8 1 d C2 C 0.14677(19) 0.6126(2) 0.19115(19) Uani 0.0560(9) 8 1 d C3 C 0.23689(18) 0.6505(2) 0.23712(18) Uani 0.0516(9) 8 1 d C4 C 0.28373(15) 0.7466(2) 0.20523(16) Uani 0.0398(7) 8 1 d C5 C 0.24680(16) 1.0692(2) -0.01147(18) Uani 0.0504(9) 8 1 d C6 C 0.1923(2) 1.1286(3) -0.0858(2) Uani 0.0635(11) 8 1 d C7 C 0.1039(2) 1.0865(3) -0.1372(2) Uani 0.0686(11) 8 1 d C8 C 0.06762(18) 0.9855(2) -0.11405(18) Uani 0.0555(10) 8 1 d C9 C 0.08060(14) 0.8180(2) -0.00994(16) Uani 0.0390(8) 8 1 d C10 C 0.27446(14) 0.90350(19) 0.09237(15) Uani 0.0350(7) 8 1 d C8a C 0.12150(14) 0.9246(2) -0.03754(15) Uani 0.0385(7) 8 1 d C9a C 0.13474(14) 0.76132(19) 0.07394(15) Uani 0.0352(7) 8 1 d C10a C 0.21291(14) 0.96563(18) 0.01297(15) Uani 0.0360(7) 8 1 d C4a C 0.23150(13) 0.80296(19) 0.12445(15) Uani 0.0332(7) 8 1 d H1 H -0.015(2) 0.558(3) 0.084(2) Uiso 0.083(11) 8 1 d H2 H 0.409(2) 0.843(3) 0.219(2) Uiso 0.083(10) 8 1 d H3 H -0.026(2) 0.659(3) 0.002(3) Uiso 0.094(11) 8 1 d H4 H 0.399(2) 0.751(3) 0.301(2) Uiso 0.070(10) 8 1 d H1c2 H 0.117435 0.548165 0.215907 Uiso 0.0672 8 1 d H1c3 H 0.270877 0.611894 0.293135 Uiso 0.062 8 1 d H1c5 H 0.308922 1.09912 0.024271 Uiso 0.0605 8 1 d H1c6 H 0.216312 1.199547 -0.101795 Uiso 0.0761 8 1 d H1c7 H 0.066661 1.127744 -0.189954 Uiso 0.0823 8 1 d H1c8 H 0.005284 0.956947 -0.150461 Uiso 0.0666 8 1 d loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _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 O1 O 0.0472(8) 0.0697(14) 0.0494(11) -0.0175(9) -0.0120(7) -0.0043(10) O2 O 0.0407(7) 0.0482(12) 0.0533(11) -0.0136(8) -0.0062(7) -0.0033(9) N1 N 0.0641(14) 0.0609(18) 0.0767(19) -0.0324(13) 0.0058(13) 0.0066(15) N2 N 0.0503(11) 0.0760(19) 0.0395(13) 0.0049(12) -0.0113(10) 0.0070(13) C1 C 0.0482(11) 0.0433(15) 0.0469(14) -0.0134(11) 0.0127(10) -0.0048(12) C2 C 0.0733(15) 0.0450(17) 0.0533(16) -0.0095(13) 0.0218(13) 0.0121(14) C3 C 0.0647(14) 0.0521(17) 0.0385(15) 0.0077(13) 0.0086(11) 0.0115(12) C4 C 0.0436(11) 0.0445(15) 0.0314(12) 0.0044(11) 0.0055(9) -0.0016(11) C5 C 0.0523(12) 0.0443(17) 0.0550(16) -0.0077(12) 0.0090(11) 0.0038(13) C6 C 0.0769(16) 0.0470(19) 0.068(2) 0.0007(14) 0.0155(15) 0.0176(15) C7 C 0.0820(17) 0.065(2) 0.0561(18) 0.0105(16) -0.0012(14) 0.0217(16) C8 C 0.0575(13) 0.060(2) 0.0450(16) 0.0012(14) -0.0058(11) 0.0046(14) C9 C 0.0345(9) 0.0475(16) 0.0339(12) -0.0061(10) 0.0010(9) -0.0073(11) C10 C 0.0343(9) 0.0363(14) 0.0339(12) -0.0044(9) 0.0034(9) -0.0055(10) C8a C 0.0408(10) 0.0440(15) 0.0299(11) 0.0006(10) 0.0029(9) 0.0002(11) C9a C 0.0359(9) 0.0380(14) 0.0319(12) -0.0056(9) 0.0056(9) -0.0039(10) C10a C 0.0391(10) 0.0353(14) 0.0346(12) -0.0024(10) 0.0086(9) 0.0002(10) C4a C 0.0352(9) 0.0358(13) 0.0283(11) -0.0022(9) 0.0038(8) -0.0022(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.003 0.002 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' H 0.000 0.000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' O 0.011 0.006 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' N 0.006 0.003 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1' 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 C1 N1 H1 118.2(17) yes C1 N1 H3 113.7(16) yes H1 N1 H3 128(2) yes C4 N2 H2 113.4(14) yes C4 N2 H4 121.3(19) yes H2 N2 H4 125(2) yes N1 C1 C2 118.9(2) yes N1 C1 C9a 122.8(2) yes C2 C1 C9a 118.35(18) yes C1 C2 C3 122.0(2) yes C1 C2 H1c2 118.9771 yes C3 C2 H1c2 118.9777 yes C2 C3 C4 121.8(2) yes C2 C3 H1c3 119.102 yes C4 C3 H1c3 119.1001 yes N2 C4 C3 118.9(2) yes N2 C4 C4a 123.0(2) yes C3 C4 C4a 118.14(17) yes C6 C5 C10a 120.89(19) yes C6 C5 H1c5 119.5537 yes C10a C5 H1c5 119.5536 yes C5 C6 C7 119.9(3) yes C5 C6 H1c6 120.0645 yes C7 C6 H1c6 120.0635 yes C6 C7 C8 120.7(2) yes C6 C7 H1c7 119.656 yes C8 C7 H1c7 119.6575 yes C7 C8 C8a 120.1(2) yes C7 C8 H1c8 119.9398 yes C8a C8 H1c8 119.9409 yes O1 C9 C8a 118.71(17) yes O1 C9 C9a 122.78(19) yes C8a C9 C9a 118.48(15) yes O2 C10 C10a 118.83(18) yes O2 C10 C4a 122.93(17) yes C10a C10 C4a 118.23(14) yes C8 C8a C9 120.28(17) yes C8 C8a C10a 119.3(2) yes C9 C8a C10a 120.38(17) yes C1 C9a C9 119.79(16) yes C1 C9a C4a 119.48(17) yes C9 C9a C4a 120.73(18) yes C5 C10a C10 119.31(16) yes C5 C10a C8a 119.05(17) yes C10 C10a C8a 121.64(18) yes C4 C4a C10 119.79(15) yes C4 C4a C9a 120.12(18) yes C10 C4a C9a 120.09(16) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C9 1.248(2) yes O2 C10 1.249(2) yes N1 C1 1.348(3) yes N1 H1 0.86(3) yes N1 H3 1.00(3) yes N2 C4 1.347(3) yes N2 H2 1.05(3) yes N2 H4 0.79(3) yes C1 C2 1.421(3) yes C1 C9a 1.404(3) yes C2 C3 1.339(3) yes C2 H1c2 0.96 yes C3 C4 1.422(3) yes C3 H1c3 0.96 yes C4 C4a 1.403(3) yes C5 C6 1.371(3) yes C5 C10a 1.399(3) yes C5 H1c5 0.96 yes C6 C7 1.368(3) yes C6 H1c6 0.96 yes C7 C8 1.377(4) yes C7 H1c7 0.96 yes C8 C8a 1.399(3) yes C8 H1c8 0.96 yes C9 C8a 1.479(3) yes C9 C9a 1.446(3) yes C10 C10a 1.476(3) yes C10 C4a 1.447(3) yes C8a C10a 1.389(2) yes C9a C4a 1.447(2) yes 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 N1 H1 O2 5_445 0.86(3) 2.33(3) 3.116(3) 153(2) yes N2 H2 O2 . 1.05(3) 1.76(3) 2.598(3) 134(2) yes N2 H2 C10 . 1.05(3) 2.41(3) 2.858(3) 104.5(16) yes N1 H3 O1 . 1.00(3) 1.78(3) 2.590(3) 136(2) yes N1 H3 C9 . 1.00(3) 2.41(3) 2.856(4) 106.2(18) yes N2 H4 O1 8_565 0.79(3) 2.20(3) 2.956(3) 161(3) yes C2 H1c2 O2 6_545 0.96 2.49 3.260(3) 137.33 yes loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 6 0 0 1916.92 2178.77 15.50 o 8 0 0 11846.91 12525.32 86.38 o 10 0 0 289.44 282.35 4.61 o 12 0 0 1.43 10.65 3.43 o 14 0 0 1028.57 1037.05 16.26 o 5 1 0 228.19 197.78 2.19 o 7 1 0 4868.19 5177.48 28.34 o 9 1 0 2.84 10.02 2.22 o 11 1 0 159.70 154.64 3.74 o 13 1 0 114.76 115.15 4.06 o 15 1 0 18.51 8.33 3.99 o 4 2 0 572.31 605.68 5.42 o 6 2 0 98.95 90.26 2.52 o 8 2 0 806.69 895.64 7.28 o 10 2 0 459.50 477.71 5.65 o 12 2 0 53.29 39.28 4.36 o 14 2 0 36.41 17.29 5.67 o 16 2 0 1.73 13.68 6.04 o 3 3 0 7.48 12.02 2.41 o 5 3 0 437.54 410.22 5.33 o 7 3 0 181.72 178.03 3.38 o 9 3 0 103.64 109.91 3.83 o 11 3 0 11.52 25.58 4.59 o 13 3 0 25.46 23.65 6.68 o 15 3 0 0.74 2.39 4.41 < 0 4 0 830.13 664.15 13.45 o 2 4 0 485.81 451.37 6.94 o 4 4 0 223.71 234.77 4.69 o 6 4 0 41.05 36.68 4.24 o 8 4 0 1.69 -4.28 4.94 < 10 4 0 20.25 33.90 5.85 o 12 4 0 205.69 209.09 8.05 o 14 4 0 201.51 213.54 11.21 o 16 4 0 4.57 19.45 7.31 o 1 5 0 4315.40 4428.17 38.59 o 3 5 0 1276.76 1285.43 15.61 o 5 5 0 5023.07 5202.75 35.54 o 7 5 0 35.63 46.95 5.49 o 9 5 0 293.96 295.65 8.04 o 11 5 0 79.60 81.01 6.39 o 13 5 0 1049.77 1163.00 18.09 o 15 5 0 8.87 10.76 4.81 o 0 6 0 6407.40 6904.99 82.07 o 2 6 0 1358.39 1304.26 16.90 o 4 6 0 607.36 634.65 10.60 o 6 6 0 1160.90 1240.98 12.85 o 8 6 0 2911.33 2965.96 24.30 o 10 6 0 59.66 35.33 8.04 o 12 6 0 518.51 509.67 13.75 o 14 6 0 23.68 4.41 14.98 < 1 7 0 851.12 904.78 15.17 o 3 7 0 1089.95 1080.59 16.15 o 5 7 0 139.96 158.77 6.97 o 7 7 0 70.23 90.06 7.56 o 9 7 0 1142.16 1079.91 14.02 o 11 7 0 94.86 103.14 10.41 o 13 7 0 70.70 89.00 13.71 o 15 7 0 28.46 35.04 6.21 o 0 8 0 15.36 51.49 14.14 o 2 8 0 32.18 5.72 10.52 < 4 8 0 251.62 227.38 10.08 o 6 8 0 1163.35 1224.61 15.20 o 8 8 0 181.90 158.75 7.30 o 10 8 0 89.22 156.64 15.17 o 12 8 0 65.47 36.66 19.54 < 14 8 0 47.89 62.70 21.74 o 1 9 0 167.92 193.74 12.33 o 3 9 0 0.01 10.40 8.00 < 5 9 0 20.28 31.85 9.56 o 7 9 0 15.64 3.37 7.17 < 9 9 0 3.17 -0.19 6.19 < 11 9 0 10.70 38.17 21.92 < 13 9 0 1.62 -129.45 25.24 < 0 10 0 18.28 24.61 12.37 < 2 10 0 222.27 261.12 14.66 o 4 10 0 98.66 71.21 11.26 o 6 10 0 20.17 35.33 9.51 o 8 10 0 6.71 -3.70 11.40 < 10 10 0 9.97 24.21 24.01 < 12 10 0 49.92 -32.38 28.98 < 1 11 0 70.08 57.67 12.18 o 3 11 0 0.08 22.77 14.73 < 5 11 0 543.02 568.68 18.74 o 7 11 0 26.49 7.61 15.03 < 9 11 0 11.06 8.84 18.05 < 11 11 0 1.37 3.49 6.06 < 0 12 0 25.52 38.31 16.94 o 2 12 0 0.95 12.66 17.59 < 4 12 0 225.14 206.05 17.89 o 6 12 0 550.61 587.90 18.39 o 8 12 0 0.09 62.24 13.77 o 10 12 0 10.70 9.90 7.84 < 1 13 0 58.51 94.76 20.01 o 3 13 0 12.21 -2.94 21.62 < 5 13 0 19.06 -26.40 16.34 < 7 13 0 386.83 399.35 16.31 o 9 13 0 8.94 27.76 9.11 o 0 14 0 20.18 -22.02 31.01 < 2 14 0 17.39 19.50 22.49 < 4 14 0 1.16 52.43 22.04 o 6 14 0 0.34 -61.69 20.99 < 1 15 0 0.52 1.31 21.58 < 3 15 0 1.77 -7.62 16.47 < 5 15 0 0.09 -66.46 31.58 < -15 1 1 412.84 389.76 8.13 o -13 1 1 242.79 253.69 5.13 o -11 1 1 42.26 39.10 3.13 o -9 1 1 394.65 418.98 4.07 o -7 1 1 656.47 790.53 5.10 o -5 1 1 0.00 7.20 1.17 o 5 1 1 5.71 8.59 1.56 o 7 1 1 2326.60 2565.56 14.89 o 9 1 1 12.73 10.22 2.38 o 11 1 1 19.74 15.47 3.12 o 13 1 1 22.64 21.61 3.24 o 15 1 1 15.88 28.59 5.35 o -16 2 1 1.87 -1.73 5.88 < -14 2 1 49.90 28.70 5.82 o -12 2 1 128.88 121.60 4.40 o -10 2 1 33.79 34.53 2.92 o -8 2 1 8.82 11.81 2.28 o -6 2 1 67.93 73.87 2.85 o -4 2 1 4519.75 4150.48 21.66 o 4 2 1 15.70 18.66 1.55 o 6 2 1 99.05 107.34 2.61 o 8 2 1 64.63 73.94 3.39 o 10 2 1 57.24 55.17 3.56 o 12 2 1 243.59 223.25 5.61 o 14 2 1 25.06 5.72 5.68 < 16 2 1 0.31 16.23 7.93 o -15 3 1 14.90 5.92 4.47 < -13 3 1 60.22 78.88 6.50 o -11 3 1 1.25 -2.09 3.77 < -9 3 1 67.34 76.91 3.55 o -7 3 1 34.82 37.71 3.19 o -5 3 1 1514.89 1499.72 10.63 o -3 3 1 1136.91 1068.00 9.87 o 3 3 1 300.07 370.73 4.99 o 5 3 1 245.61 226.61 5.31 o 7 3 1 55.13 34.13 3.96 o 9 3 1 610.75 659.46 8.65 o 11 3 1 641.84 587.47 8.82 o 13 3 1 259.65 241.84 9.22 o 15 3 1 26.88 41.36 5.82 o -16 4 1 5.91 10.33 7.08 < -14 4 1 223.05 189.87 8.36 o -12 4 1 86.78 93.85 5.75 o -10 4 1 57.97 58.51 5.06 o -8 4 1 72.07 60.87 4.21 o -6 4 1 97.34 89.09 3.23 o -4 4 1 16.87 8.88 4.74 < -2 4 1 576.16 582.55 8.17 o 0 4 1 534.15 557.33 7.57 o 2 4 1 751.28 676.51 9.02 o 4 4 1 5.36 4.74 3.63 < 6 4 1 4.80 -21.26 5.23 < 8 4 1 4.66 0.29 4.60 < 10 4 1 4.34 11.59 5.84 < 12 4 1 550.73 611.60 12.79 o 14 4 1 61.40 45.96 9.78 o 16 4 1 23.42 38.20 7.55 o -15 5 1 29.12 85.31 16.04 o -13 5 1 210.15 236.54 11.58 o -11 5 1 60.22 51.58 5.86 o -9 5 1 1241.42 1238.10 13.04 o -7 5 1 438.11 460.37 5.59 o -5 5 1 596.99 583.01 8.05 o -3 5 1 1442.09 1376.36 13.12 o -1 5 1 12606.65 12787.64 96.95 o 1 5 1 153.70 140.57 5.56 o 3 5 1 1577.86 1632.36 18.31 o 5 5 1 3063.49 3175.30 26.32 o 7 5 1 310.68 358.01 7.94 o 9 5 1 5.11 1.32 6.04 < 11 5 1 750.21 784.80 11.80 o 13 5 1 833.60 836.31 16.44 o 15 5 1 3.58 2.71 4.80 < -14 6 1 0.03 -48.91 13.35 < -12 6 1 0.26 -2.65 10.44 < -10 6 1 685.19 719.79 11.37 o -8 6 1 3399.93 3279.70 22.33 o -6 6 1 606.78 574.84 8.16 o -4 6 1 110.35 91.28 6.00 o -2 6 1 5239.61 5604.61 48.83 o 0 6 1 2643.05 2711.70 24.65 o 2 6 1 128.49 144.78 6.90 o 4 6 1 1621.63 1688.22 19.54 o 6 6 1 842.20 904.33 11.32 o 8 6 1 0.12 -1.66 5.90 < 10 6 1 23.00 17.17 8.84 < 12 6 1 72.37 92.35 11.24 o 14 6 1 20.64 39.14 13.41 o -15 7 1 112.46 138.95 47.57 o -13 7 1 3.92 -3.51 11.01 < -11 7 1 3.60 -5.59 7.95 < -9 7 1 2542.00 2437.61 18.36 o -7 7 1 724.41 700.58 9.41 o -5 7 1 3.01 1.65 5.89 < -3 7 1 140.10 137.38 5.92 o -1 7 1 1790.60 1720.18 18.70 o 1 7 1 18.75 15.40 8.20 < 3 7 1 268.68 259.97 9.92 o 5 7 1 722.01 772.26 14.33 o 7 7 1 1558.22 1517.01 14.23 o 9 7 1 81.83 43.85 8.42 o 11 7 1 143.38 131.97 15.25 o 13 7 1 11.37 34.16 13.67 o -14 8 1 3.29 30.43 19.82 < -12 8 1 58.68 62.81 15.69 o -10 8 1 26.70 34.56 10.30 o -8 8 1 5.49 -7.25 5.17 < -6 8 1 1.51 -13.52 7.44 < -4 8 1 79.15 70.28 6.90 o -2 8 1 196.99 232.94 9.07 o 0 8 1 1381.53 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182.66 178.39 15.99 o -2 2 13 99.62 98.71 16.28 o 0 2 13 0.40 27.42 12.24 o 2 2 13 0.81 -13.63 10.96 < 4 2 13 613.66 626.34 14.43 o 6 2 13 6.45 33.03 13.58 o 8 2 13 46.70 43.74 23.77 < -11 3 13 33.63 6.20 21.26 < -9 3 13 3.68 -63.58 20.02 < -7 3 13 0.76 75.94 18.90 o -5 3 13 934.39 971.14 25.70 o -3 3 13 61.58 40.95 20.52 < -1 3 13 32.02 54.96 13.50 o 1 3 13 106.57 109.23 11.66 o 3 3 13 1327.56 1310.41 20.21 o 5 3 13 5.10 -14.67 14.33 < 7 3 13 88.91 129.97 19.78 o 9 3 13 174.04 342.37 32.79 o -12 4 13 95.72 73.54 23.57 o -10 4 13 9.46 140.20 24.60 o -8 4 13 48.23 72.54 21.90 o -6 4 13 1171.65 1177.66 31.92 o -4 4 13 1201.90 1356.60 30.16 o -2 4 13 23.92 77.32 17.68 o 0 4 13 78.24 60.47 12.38 o 2 4 13 958.76 881.76 18.05 o 4 4 13 12.55 31.05 14.42 o 6 4 13 80.19 105.16 19.92 o 8 4 13 22.41 62.85 36.04 < -11 5 13 45.56 0.88 39.71 < -9 5 13 50.54 37.45 27.86 < -7 5 13 96.81 111.93 26.80 o -5 5 13 580.54 599.13 25.01 o -3 5 13 11.55 10.29 15.01 < -1 5 13 85.05 105.05 15.72 o 1 5 13 2.12 -32.69 15.46 < 3 5 13 2.39 -4.01 16.72 < 5 5 13 31.11 28.24 18.30 < 7 5 13 11.17 -29.50 32.16 < -10 6 13 13.71 119.56 33.34 o -8 6 13 20.45 -16.73 27.52 < -6 6 13 14.14 -10.90 26.95 < -4 6 13 30.59 22.94 18.82 < -2 6 13 1.44 40.06 17.24 o 0 6 13 0.13 -21.51 14.54 < 2 6 13 31.96 8.60 16.37 < 4 6 13 1.87 -12.60 20.30 < 6 6 13 6.56 0.07 21.58 < -9 7 13 96.16 122.41 27.97 o -7 7 13 1.50 -36.57 32.40 < -5 7 13 0.21 -48.58 23.50 < -3 7 13 3.61 -32.69 22.73 < -1 7 13 15.83 -57.64 19.64 < 1 7 13 14.17 8.75 21.62 < 3 7 13 61.58 61.28 19.25 o 5 7 13 0.16 3.97 21.61 < 7 7 13 38.14 16.97 6.79 o -8 8 13 14.44 28.28 25.78 < -6 8 13 0.00 -17.32 23.50 < -4 8 13 40.82 46.16 24.79 < -2 8 13 5.14 65.44 27.40 o 0 8 13 87.97 87.36 20.01 o 2 8 13 6.05 120.30 23.97 o 4 8 13 39.70 -14.04 27.38 < 6 8 13 1.78 -21.97 6.31 < -7 9 13 52.07 40.97 7.66 o -5 9 13 82.98 64.30 8.66 o -3 9 13 18.48 18.69 5.90 o -1 9 13 22.25 22.06 4.63 o 1 9 13 142.38 312.55 28.48 o 3 9 13 134.41 156.50 29.88 o -6 10 13 54.15 109.59 7.72 o -4 10 13 17.77 0.24 6.85 < -2 10 13 10.75 6.96 5.66 < 0 10 13 306.33 384.19 10.84 o 2 10 13 57.93 71.94 6.26 o -12 0 14 2.12 -12.22 8.25 < -10 0 14 37.74 -97.11 27.50 < -8 0 14 0.79 17.42 27.06 < -6 0 14 8.53 -58.46 28.77 < -4 0 14 139.40 120.22 26.98 o -2 0 14 3.86 78.09 28.86 o 0 0 14 15.44 113.76 24.19 o 2 0 14 78.92 88.50 20.17 o 4 0 14 158.19 251.09 22.79 o 6 0 14 203.34 249.77 20.10 o 8 0 14 20.58 -41.33 43.02 < -11 1 14 58.54 79.68 16.34 o -9 1 14 1.69 48.44 20.51 o -7 1 14 14.45 -19.61 20.72 < -5 1 14 9.99 -43.30 18.68 < -3 1 14 4.02 3.11 18.19 < -1 1 14 2.13 20.75 17.76 < 1 1 14 1.86 -42.68 17.60 < 3 1 14 12.88 16.08 15.98 < 5 1 14 0.30 16.26 17.27 < 7 1 14 59.85 63.07 27.53 o -12 2 14 1.96 33.65 5.68 o -10 2 14 0.03 -30.58 19.03 < -8 2 14 17.42 58.20 24.63 o -6 2 14 0.04 -24.82 21.50 < -4 2 14 29.85 10.17 19.22 < -2 2 14 4.65 -35.87 20.48 < 0 2 14 80.46 122.37 16.29 o 2 2 14 114.75 132.08 17.64 o 4 2 14 14.12 69.24 17.17 o 6 2 14 7.86 13.48 21.88 < 8 2 14 25.53 -29.46 28.43 < -11 3 14 2.86 36.04 20.31 < -9 3 14 57.31 65.90 26.28 o -7 3 14 0.41 43.84 24.94 < -5 3 14 761.09 771.03 25.79 o -3 3 14 3.21 -74.00 21.89 < -1 3 14 0.03 11.01 21.23 < 1 3 14 877.73 965.88 23.82 o 3 3 14 81.09 123.40 22.48 o 5 3 14 10.45 40.05 28.65 < 7 3 14 45.09 161.16 30.38 o -10 4 14 19.15 11.41 27.67 < -8 4 14 7.77 73.58 27.23 o -6 4 14 58.92 72.56 27.48 o -4 4 14 138.94 60.32 23.45 o -2 4 14 7.13 44.14 23.36 < 0 4 14 95.65 86.49 19.01 o 2 4 14 450.38 531.47 22.19 o 4 4 14 67.61 67.53 21.78 o 6 4 14 32.15 42.70 26.94 < -9 5 14 2.81 38.30 27.41 < -7 5 14 138.78 260.96 32.18 o -5 5 14 61.55 -66.38 33.01 < -3 5 14 7.04 -49.34 25.39 < -1 5 14 2.73 5.55 18.95 < 1 5 14 392.24 448.36 19.85 o 3 5 14 12.40 31.54 16.07 < 5 5 14 0.03 12.61 27.21 < 7 5 14 0.01 24.98 5.56 o -10 6 14 2.53 -17.93 8.10 < -8 6 14 2.47 -26.48 26.48 < -6 6 14 149.06 127.27 25.39 o -4 6 14 36.29 12.39 27.58 < -2 6 14 8.54 -3.00 21.56 < 0 6 14 107.14 122.20 17.95 o 2 6 14 72.81 34.98 15.41 o 4 6 14 0.49 -6.42 20.83 < 6 6 14 0.19 -29.84 24.34 < -9 7 14 27.99 29.07 7.35 o -7 7 14 14.55 10.52 7.06 < -5 7 14 5.99 3.26 5.94 < -3 7 14 0.00 2.37 5.05 < -1 7 14 4.36 -32.01 25.93 < 1 7 14 66.95 36.33 18.83 < 3 7 14 48.83 104.11 20.04 o 5 7 14 6.50 -43.55 26.83 < -8 8 14 17.42 33.18 6.79 o -6 8 14 149.10 156.84 8.93 o -4 8 14 2.71 24.25 7.46 o -2 8 14 17.31 33.91 5.63 o 0 8 14 8.55 6.69 4.99 < 2 8 14 8.78 57.51 19.53 o 4 8 14 16.99 52.91 39.32 < -5 9 14 2.78 1.95 6.01 < -3 9 14 18.27 18.99 8.70 o -1 9 14 92.18 94.08 7.27 o 1 9 14 44.86 61.03 7.07 o -11 1 15 0.01 16.37 6.78 o -9 1 15 27.79 16.36 4.89 o -7 1 15 136.54 96.18 22.00 o -5 1 15 12.96 131.69 22.30 o -3 1 15 0.77 -43.80 15.69 < -1 1 15 17.39 97.01 31.23 o 1 1 15 134.82 85.75 23.88 o 3 1 15 0.51 -53.34 19.33 < 5 1 15 38.19 78.29 34.81 o 7 1 15 305.14 215.54 37.76 o -10 2 15 2.85 -19.03 4.91 < -8 2 15 296.25 271.74 22.87 o -6 2 15 200.69 138.86 23.34 o -4 2 15 25.67 53.38 25.83 o -2 2 15 3.95 -22.82 27.85 < 0 2 15 164.30 184.51 25.26 o 2 2 15 110.72 98.57 24.13 o 4 2 15 7.94 42.52 25.72 < 6 2 15 196.81 195.57 29.86 o -9 3 15 36.64 11.25 6.10 < -7 3 15 789.45 806.12 26.40 o -5 3 15 98.33 120.21 25.76 o -3 3 15 30.59 -10.20 31.27 < -1 3 15 232.48 182.96 26.32 o 1 3 15 466.98 459.02 23.56 o 3 3 15 0.03 39.14 26.15 < 5 3 15 16.89 -39.17 30.98 < -10 4 15 3.59 27.02 7.13 o -8 4 15 3.24 -27.23 6.34 < -6 4 15 368.66 343.43 27.73 o -4 4 15 65.72 72.46 25.02 o -2 4 15 28.12 117.37 27.53 o 0 4 15 338.01 300.38 29.18 o 2 4 15 604.56 570.91 22.05 o 4 4 15 7.97 -45.12 30.15 < 6 4 15 21.00 -18.14 30.96 < -9 5 15 19.33 22.21 7.19 o -7 5 15 12.21 65.43 7.57 o -5 5 15 97.03 114.37 7.47 o -3 5 15 0.21 -8.29 5.86 < -1 5 15 6.21 29.00 23.60 < 1 5 15 633.35 624.80 28.35 o 3 5 15 93.13 112.82 31.25 o 5 5 15 41.89 43.52 31.36 < -8 6 15 0.56 24.63 7.38 o -6 6 15 2.17 17.48 7.45 o -4 6 15 12.42 -7.90 6.23 < -2 6 15 5.89 -8.93 5.70 < 0 6 15 14.92 32.94 5.96 o 2 6 15 17.60 45.24 19.30 o 4 6 15 36.52 -75.92 55.02 < -7 7 15 0.76 -14.54 7.36 < -5 7 15 14.63 15.92 7.03 o -3 7 15 0.01 -21.85 6.30 < -1 7 15 5.55 -23.43 6.79 < 1 7 15 2.04 -17.78 6.51 < 3 7 15 5.20 -11.16 8.79 < -4 8 15 5.85 -11.81 8.05 < -2 8 15 79.14 130.61 8.30 o 0 8 15 5.39 11.72 6.67 < -8 0 16 388.07 417.95 14.81 o -6 0 16 21.00 -0.14 7.99 < -4 0 16 4.58 12.95 7.78 < -2 0 16 0.11 -16.97 6.71 < 0 0 16 392.38 495.47 46.05 o 2 0 16 55.23 61.23 12.51 o 4 0 16 0.17 39.84 11.73 o -9 1 16 4.78 -4.81 6.87 < -7 1 16 248.33 267.12 9.07 o -5 1 16 37.84 30.89 8.61 o -3 1 16 26.16 20.03 7.77 o -1 1 16 20.51 -8.79 26.16 < 1 1 16 102.82 160.37 30.27 o 3 1 16 14.76 38.56 8.29 o 5 1 16 17.59 18.24 7.75 o -8 2 16 497.95 502.81 11.74 o -6 2 16 232.49 245.14 8.47 o -4 2 16 2.59 -3.58 6.29 < -2 2 16 50.79 40.45 7.21 o 0 2 16 163.38 125.80 7.70 o 2 2 16 36.53 38.97 9.56 o 4 2 16 3.48 -10.13 8.16 < -7 3 16 99.67 108.02 7.22 o -5 3 16 1.91 -10.65 5.93 < -3 3 16 6.53 5.20 6.76 < -1 3 16 0.27 -9.94 5.95 < 1 3 16 22.29 0.82 7.03 < 3 3 16 13.95 -4.58 8.35 < -8 4 16 2.12 5.93 8.30 < -6 4 16 10.17 -2.28 7.38 < -4 4 16 11.01 9.53 6.91 < -2 4 16 20.32 15.07 7.62 < 0 4 16 99.57 76.82 6.79 o 4 4 16 10.87 13.35 7.81 < -7 5 16 10.50 14.47 8.92 < -5 5 16 0.02 -4.44 6.41 < -3 5 16 0.11 27.16 6.79 o -1 5 16 178.31 186.75 8.06 o 1 5 16 23.33 7.46 8.27 < 3 5 16 0.02 -41.75 8.96 < -6 6 16 1.29 0.51 8.15 < -4 6 16 4.14 -19.68 7.81 < -2 6 16 121.66 148.56 8.79 o 0 6 16 25.42 11.80 6.63 < 2 6 16 2.80 17.74 7.09 o -3 7 16 61.19 66.06 8.12 o -1 7 16 3.95 -31.71 8.04 < -7 1 17 41.64 27.96 7.69 o -5 1 17 5.38 4.62 5.59 < -3 1 17 41.41 68.26 7.37 o -1 1 17 0.82 -6.93 8.85 < 1 1 17 0.26 15.65 8.55 < -6 2 17 101.94 111.13 7.55 o -4 2 17 0.26 12.75 7.99 < -2 2 17 20.45 22.86 7.49 o 0 2 17 70.35 68.95 9.25 o 2 2 17 3.66 8.76 8.92 < -5 3 17 0.99 46.32 7.81 o -3 3 17 9.39 -16.79 6.62 < -1 3 17 11.96 4.60 7.14 < 1 3 17 26.32 -6.70 13.75 < -4 4 17 0.57 5.35 8.06 < -2 4 17 14.27 6.11 6.79 < 0 4 17 35.91 17.06 6.56 o loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 29150 2 PubChem 31420