#------------------------------------------------------------------------------ #$Date: 2020-04-05 13:25:56 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250215 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557207.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_1557207 loop_ _publ_author_name 'Chen, Hang' 'Ye, Hebo' 'Hai, Yu' 'Zhang, Ling' 'You, Lei' _publ_section_title ; n \\rightarrow \p* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media ; _journal_issue 10 _journal_name_full 'Chemical Science' _journal_page_first 2707 _journal_paper_doi 10.1039/C9SC05698J _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C6 H14 N, C13 H15 N2 O2' _chemical_formula_sum 'C19 H29 N3 O2' _chemical_formula_weight 331.45 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-05-28 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-10 deposited with the CCDC. 2020-01-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.23(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.03(2) _cell_length_b 10.580(10) _cell_length_c 22.26(4) _cell_measurement_reflns_used 5066 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.4816 _cell_measurement_theta_min 3.4154 _cell_volume 3904(9) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 173.15 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_unetI/netI 0.0522 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 15452 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.439 _diffrn_reflns_theta_min 3.415 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.128 _exptl_crystal_description Prism _exptl_crystal_F_000 1440 _refine_diff_density_max 0.290 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 4421 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.1482 _refine_ls_R_factor_gt 0.0880 _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^)+(0.1378P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2275 _refine_ls_wR_factor_ref 0.2777 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2404 _reflns_number_total 4421 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05698j2.cif _cod_data_source_block 2focb _cod_depositor_comments 'Adding full bibliography for 1557206--1557207.cif.' _cod_original_cell_volume 3903(9) _cod_database_code 1557207 _shelxl_version_number 2014/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups 2. Rigid bond restraints C3, N6 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02 N6, C17 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02 3.a Ternary CH refined with riding coordinates: C5(H5), C14(H14) 3.b Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A, H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B) 3.c Aromatic/amide H refined with riding coordinates: C9(H9), C10(H10), C15(H15), C17(H17) ; _shelx_res_file ; TITL a in I2/a CELL 0.71073 17.0266 10.5797 22.2586 90 103.226 90 ZERR 8 0.021 0.0102 0.0353 0 0.025 0 LATT 2 SYMM 0.5-X,+Y,-Z SFAC C H N O UNIT 152 232 24 16 DELU 0.02 0.02 C3 N6 DELU 0.02 0.02 N6 C17 L.S. 4 PLAN 20 TEMP -100 GRID BOND fmap 2 acta MERG 2 REM REM REM WGHT 0.137800 FVAR 0.28442 N1 3 0.083556 0.151910 0.342067 11.00000 0.05275 0.06182 = 0.06604 -0.00214 0.01854 -0.00430 H1A 2 0.075523 0.220979 0.309413 11.00000 -1.20000 H1B 2 0.050861 0.082134 0.336170 11.00000 -1.20000 N2 3 0.265808 0.514743 0.154195 11.00000 0.05125 0.05400 = 0.07826 -0.00021 0.01636 0.00074 C3 1 0.187878 0.333150 0.170276 11.00000 0.04332 0.05277 = 0.05744 0.00234 0.00360 -0.00112 O4 4 0.026363 0.454637 0.168588 11.00000 0.06246 0.07085 = 0.09334 0.02376 0.02433 0.01407 C5 1 0.274279 0.652501 0.150842 11.00000 0.05001 0.05093 = 0.07760 0.00364 0.01830 0.00273 AFIX 13 H5 2 0.222327 0.693959 0.153303 11.00000 -1.20000 AFIX 0 N6 3 0.245064 0.257305 0.155565 11.00000 0.05412 0.05503 = 0.08699 0.00049 0.01634 0.00519 C7 1 0.120098 0.285578 0.188562 11.00000 0.04777 0.05963 = 0.05657 0.00479 0.00615 -0.00281 O8 4 0.041386 0.349253 0.257333 11.00000 0.06746 0.08502 = 0.08073 0.01146 0.02882 0.00535 C9 1 0.111854 0.154304 0.189956 11.00000 0.06058 0.05540 = 0.07277 0.00594 0.01072 -0.00641 AFIX 43 H9 2 0.067277 0.118134 0.202750 11.00000 -1.20000 AFIX 0 C10 1 0.202011 0.471429 0.166462 11.00000 0.04680 0.05185 = 0.06581 -0.00428 0.01054 0.00190 AFIX 43 H10 2 0.162050 0.528710 0.173427 11.00000 -1.20000 AFIX 0 C11 1 0.057406 0.370316 0.206408 11.00000 0.04103 0.05564 = 0.07537 0.00279 0.01193 -0.00464 C12 1 0.360887 0.835254 0.200405 11.00000 0.06943 0.05742 = 0.07589 -0.00351 0.01032 -0.00339 AFIX 23 H12A 2 0.314015 0.886681 0.204950 11.00000 -1.20000 H12B 2 0.407147 0.857916 0.234493 11.00000 -1.20000 AFIX 0 C13 1 0.341020 0.694742 0.205449 11.00000 0.06088 0.05974 = 0.07271 0.00313 0.01529 -0.00088 AFIX 23 H13A 2 0.390092 0.643670 0.206714 11.00000 -1.20000 H13B 2 0.323572 0.679981 0.244350 11.00000 -1.20000 AFIX 0 C14 1 0.074702 0.216640 0.399641 11.00000 0.06540 0.07631 = 0.06751 -0.00843 0.01262 0.00085 AFIX 13 H14 2 0.113692 0.288693 0.408053 11.00000 -1.20000 AFIX 0 C15 1 0.167863 0.077526 0.172927 11.00000 0.07582 0.04840 = 0.08649 0.00260 0.01412 0.00190 AFIX 43 H15 2 0.161674 -0.011742 0.172068 11.00000 -1.20000 AFIX 0 C16 1 0.294655 0.685589 0.089990 11.00000 0.09034 0.06696 = 0.07073 -0.00568 0.01783 -0.00934 AFIX 23 H16A 2 0.248908 0.661939 0.055690 11.00000 -1.20000 H16B 2 0.342409 0.636330 0.085482 11.00000 -1.20000 AFIX 0 C17 1 0.234338 0.134178 0.156860 11.00000 0.06849 0.05450 = 0.09978 -0.00748 0.02373 0.00744 AFIX 43 H17 2 0.274003 0.080860 0.146282 11.00000 -1.20000 AFIX 0 C18 1 0.381273 0.866262 0.139689 11.00000 0.06996 0.05711 = 0.10334 0.00257 0.02726 -0.00697 AFIX 23 H18A 2 0.431160 0.821165 0.136641 11.00000 -1.20000 H18B 2 0.391283 0.958155 0.137578 11.00000 -1.20000 AFIX 0 C19 1 0.312410 0.827761 0.085798 11.00000 0.09136 0.06747 = 0.07519 0.00765 0.02716 -0.00094 AFIX 23 H19A 2 0.327503 0.845890 0.046277 11.00000 -1.20000 H19B 2 0.263466 0.877317 0.086981 11.00000 -1.20000 AFIX 0 C20 1 -0.009691 0.268517 0.391874 11.00000 0.08650 0.10252 = 0.08213 -0.00546 0.03009 0.02820 AFIX 23 H20A 2 -0.049208 0.198786 0.381240 11.00000 -1.20000 H20B 2 -0.020584 0.330237 0.357536 11.00000 -1.20000 AFIX 0 C21 1 0.094840 0.125571 0.453119 11.00000 0.13861 0.11087 = 0.07119 0.00069 0.01557 0.03928 AFIX 23 H21A 2 0.151715 0.098043 0.459417 11.00000 -1.20000 H21B 2 0.059956 0.049874 0.444031 11.00000 -1.20000 AFIX 0 C22 1 -0.019969 0.333315 0.451412 11.00000 0.16488 0.13148 = 0.10808 -0.01005 0.06099 0.04620 AFIX 23 H22A 2 0.016287 0.407520 0.460069 11.00000 -1.20000 H22B 2 -0.076192 0.363646 0.445762 11.00000 -1.20000 AFIX 0 C23 1 0.081522 0.191691 0.513042 11.00000 0.20156 0.22705 = 0.05994 -0.01157 0.00880 0.04987 AFIX 23 H23A 2 0.089587 0.129260 0.547036 11.00000 -1.20000 H23B 2 0.121995 0.259654 0.525264 11.00000 -1.20000 AFIX 0 C24 1 -0.001475 0.246870 0.503400 11.00000 0.18407 0.21640 = 0.08785 -0.00861 0.05957 0.06304 AFIX 23 H24A 2 -0.041523 0.177446 0.496441 11.00000 -1.20000 H24B 2 -0.006284 0.292406 0.541248 11.00000 -1.20000 AFIX 0 H1C 2 0.137589 0.116967 0.342099 11.00000 0.07815 HKLF 4 REM a in I2/a REM R1 = 0.0880 for 2404 Fo > 4sig(Fo) and 0.1482 for all 4421 data REM 227 parameters refined using 2 restraints END WGHT 0.1378 0.0000 REM Highest difference peak 0.290, deepest hole -0.181, 1-sigma level 0.047 Q1 1 0.1478 0.2431 0.5073 11.00000 0.05 0.27 Q2 1 0.1063 0.3034 0.5020 11.00000 0.05 0.20 Q3 1 0.1252 0.2267 0.4440 11.00000 0.05 0.19 Q4 1 0.0367 0.3434 0.3747 11.00000 0.05 0.14 Q5 1 0.2746 0.9061 0.1425 11.00000 0.05 0.14 Q6 1 0.1297 0.3018 0.3896 11.00000 0.05 0.13 Q7 1 0.1714 0.3868 0.5195 11.00000 0.05 0.13 Q8 1 0.3913 0.5953 0.1377 11.00000 0.05 0.12 Q9 1 0.4244 0.9830 0.1612 11.00000 0.05 0.12 Q10 1 0.1537 0.0305 0.3678 11.00000 0.05 0.11 Q11 1 0.3981 0.6044 0.1765 11.00000 0.05 0.11 Q12 1 0.3237 0.6440 0.0708 11.00000 0.05 0.11 Q13 1 -0.0423 0.1960 0.4495 11.00000 0.05 0.11 Q14 1 0.0426 0.2105 0.2063 11.00000 0.05 0.11 Q15 1 0.2657 0.3643 0.2372 11.00000 0.05 0.11 Q16 1 0.0783 0.4234 0.1404 11.00000 0.05 0.11 Q17 1 0.3598 0.5973 0.1400 11.00000 0.05 0.10 Q18 1 0.0927 -0.0152 0.1977 11.00000 0.05 0.10 Q19 1 0.0631 0.4047 0.4634 11.00000 0.05 0.10 Q20 1 0.0269 0.3492 0.5533 11.00000 0.05 0.10 ; _shelx_res_checksum 6067 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -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 N1 N 0.08356(17) 0.1519(3) 0.34207(12) 0.0594(7) Uani 1 1 d . . H1A H 0.0755(19) 0.221(3) 0.3094(15) 0.071 Uiso 1 1 d R . H1B H 0.051(2) 0.082(3) 0.3362(14) 0.071 Uiso 1 1 d R . N2 N 0.26581(14) 0.5147(2) 0.15420(12) 0.0609(7) Uani 1 1 d . . C3 C 0.18788(16) 0.3332(3) 0.17028(12) 0.0525(7) Uani 1 1 d . U O4 O 0.02636(14) 0.4546(2) 0.16859(11) 0.0745(7) Uani 1 1 d . . C5 C 0.27428(18) 0.6525(3) 0.15084(14) 0.0589(7) Uani 1 1 d . . H5 H 0.2223 0.6940 0.1533 0.071 Uiso 1 1 calc R . N6 N 0.24506(15) 0.2573(3) 0.15557(13) 0.0653(7) Uani 1 1 d . U C7 C 0.12010(17) 0.2856(3) 0.18856(13) 0.0556(7) Uani 1 1 d . . O8 O 0.04139(14) 0.3493(2) 0.25733(11) 0.0758(7) Uani 1 1 d . . C9 C 0.11185(19) 0.1543(3) 0.18996(14) 0.0636(8) Uani 1 1 d . . H9 H 0.0673 0.1181 0.2028 0.076 Uiso 1 1 calc R . C10 C 0.20201(17) 0.4714(3) 0.16646(13) 0.0552(7) Uani 1 1 d . . H10 H 0.1620 0.5287 0.1734 0.066 Uiso 1 1 calc R . C11 C 0.05741(17) 0.3703(3) 0.20641(15) 0.0576(7) Uani 1 1 d . . C12 C 0.3609(2) 0.8353(3) 0.20041(15) 0.0686(9) Uani 1 1 d . . H12A H 0.3140 0.8867 0.2050 0.082 Uiso 1 1 calc R . H12B H 0.4071 0.8579 0.2345 0.082 Uiso 1 1 calc R . C13 C 0.3410(2) 0.6947(3) 0.20545(15) 0.0644(8) Uani 1 1 d . . H13A H 0.3901 0.6437 0.2067 0.077 Uiso 1 1 calc R . H13B H 0.3236 0.6800 0.2443 0.077 Uiso 1 1 calc R . C14 C 0.0747(2) 0.2166(3) 0.39964(15) 0.0702(9) Uani 1 1 d . . H14 H 0.1137 0.2887 0.4081 0.084 Uiso 1 1 calc R . C15 C 0.1679(2) 0.0775(3) 0.17293(16) 0.0710(9) Uani 1 1 d . . H15 H 0.1617 -0.0117 0.1721 0.085 Uiso 1 1 calc R . C16 C 0.2947(2) 0.6856(3) 0.08999(16) 0.0761(10) Uani 1 1 d . . H16A H 0.2489 0.6619 0.0557 0.091 Uiso 1 1 calc R . H16B H 0.3424 0.6363 0.0855 0.091 Uiso 1 1 calc R . C17 C 0.2343(2) 0.1342(3) 0.15686(17) 0.0735(9) Uani 1 1 d . U H17 H 0.2740 0.0809 0.1463 0.088 Uiso 1 1 calc R . C18 C 0.3813(2) 0.8663(3) 0.13969(18) 0.0756(9) Uani 1 1 d . . H18A H 0.4312 0.8212 0.1366 0.091 Uiso 1 1 calc R . H18B H 0.3913 0.9582 0.1376 0.091 Uiso 1 1 calc R . C19 C 0.3124(2) 0.8278(3) 0.08580(16) 0.0767(10) Uani 1 1 d . . H19A H 0.3275 0.8459 0.0463 0.092 Uiso 1 1 calc R . H19B H 0.2635 0.8773 0.0870 0.092 Uiso 1 1 calc R . C20 C -0.0097(3) 0.2685(4) 0.39187(18) 0.0886(12) Uani 1 1 d . . H20A H -0.0492 0.1988 0.3812 0.106 Uiso 1 1 calc R . H20B H -0.0206 0.3302 0.3575 0.106 Uiso 1 1 calc R . C21 C 0.0948(3) 0.1256(4) 0.45312(17) 0.1083(16) Uani 1 1 d . . H21A H 0.1517 0.0980 0.4594 0.130 Uiso 1 1 calc R . H21B H 0.0600 0.0499 0.4440 0.130 Uiso 1 1 calc R . C22 C -0.0200(4) 0.3333(6) 0.4514(2) 0.130(2) Uani 1 1 d . . H22A H 0.0163 0.4075 0.4601 0.156 Uiso 1 1 calc R . H22B H -0.0762 0.3636 0.4458 0.156 Uiso 1 1 calc R . C23 C 0.0815(5) 0.1917(7) 0.5130(2) 0.166(3) Uani 1 1 d . . H23A H 0.0896 0.1293 0.5470 0.199 Uiso 1 1 calc R . H23B H 0.1220 0.2597 0.5253 0.199 Uiso 1 1 calc R . C24 C -0.0015(5) 0.2469(7) 0.5034(3) 0.158(3) Uani 1 1 d . . H24A H -0.0415 0.1774 0.4964 0.190 Uiso 1 1 calc R . H24B H -0.0063 0.2924 0.5412 0.190 Uiso 1 1 calc R . H1C H 0.138(2) 0.117(3) 0.3421(15) 0.078(10) Uiso 1 1 d . . 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 0.0528(16) 0.0618(17) 0.0660(16) -0.0021(13) 0.0185(11) -0.0043(12) N2 0.0513(15) 0.0540(15) 0.0783(16) -0.0002(12) 0.0164(12) 0.0007(11) C3 0.0433(15) 0.0528(17) 0.0574(16) 0.0023(12) 0.0036(11) -0.0011(12) O4 0.0625(14) 0.0709(16) 0.0933(16) 0.0238(12) 0.0243(11) 0.0141(11) C5 0.0500(17) 0.0509(17) 0.0776(19) 0.0036(14) 0.0183(14) 0.0027(13) N6 0.0541(16) 0.0550(16) 0.0870(18) 0.0005(12) 0.0163(13) 0.0052(12) C7 0.0478(16) 0.0596(18) 0.0566(16) 0.0048(13) 0.0061(12) -0.0028(13) O8 0.0675(15) 0.0850(17) 0.0807(16) 0.0115(12) 0.0288(12) 0.0054(12) C9 0.0606(19) 0.0554(19) 0.0728(19) 0.0059(15) 0.0107(14) -0.0064(14) C10 0.0468(16) 0.0518(17) 0.0658(17) -0.0043(13) 0.0105(12) 0.0019(12) C11 0.0410(15) 0.0556(18) 0.075(2) 0.0028(14) 0.0119(13) -0.0046(13) C12 0.069(2) 0.057(2) 0.076(2) -0.0035(15) 0.0103(16) -0.0034(15) C13 0.061(2) 0.0597(19) 0.0727(19) 0.0031(15) 0.0153(15) -0.0009(15) C14 0.065(2) 0.076(2) 0.068(2) -0.0084(16) 0.0126(15) 0.0009(16) C15 0.076(2) 0.0484(18) 0.086(2) 0.0026(15) 0.0141(17) 0.0019(16) C16 0.090(3) 0.067(2) 0.071(2) -0.0057(16) 0.0178(17) -0.0093(18) C17 0.068(2) 0.055(2) 0.100(2) -0.0075(17) 0.0237(18) 0.0074(16) C18 0.070(2) 0.057(2) 0.103(3) 0.0026(17) 0.0273(18) -0.0070(16) C19 0.091(3) 0.067(2) 0.075(2) 0.0077(17) 0.0272(18) -0.0009(18) C20 0.087(3) 0.103(3) 0.082(2) -0.005(2) 0.030(2) 0.028(2) C21 0.139(4) 0.111(4) 0.071(2) 0.001(2) 0.016(2) 0.039(3) C22 0.165(5) 0.131(5) 0.108(4) -0.010(3) 0.061(4) 0.046(4) C23 0.202(7) 0.227(8) 0.060(3) -0.012(3) 0.009(3) 0.050(6) C24 0.184(7) 0.216(7) 0.088(3) -0.009(4) 0.060(4) 0.063(5) 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 C10 N2 C5 118.0(3) N6 C3 C7 122.7(3) N6 C3 C10 115.6(3) C7 C3 C10 121.6(3) N2 C5 C13 108.3(2) N2 C5 C16 108.7(3) C16 C5 C13 111.3(3) C17 N6 C3 117.9(3) C3 C7 C11 122.7(3) C9 C7 C3 117.2(3) C9 C7 C11 120.1(3) C15 C9 C7 120.2(3) N2 C10 C3 121.8(3) O4 C11 C7 117.3(3) O8 C11 O4 126.2(3) O8 C11 C7 116.6(3) C18 C12 C13 112.1(3) C5 C13 C12 111.2(3) N1 C14 C20 110.4(3) N1 C14 C21 109.6(3) C21 C14 C20 111.2(3) C9 C15 C17 118.2(3) C5 C16 C19 111.6(3) N6 C17 C15 123.7(3) C12 C18 C19 110.7(3) C18 C19 C16 109.8(3) C14 C20 C22 110.9(4) C14 C21 C23 109.6(4) C24 C22 C20 111.1(4) C24 C23 C21 111.5(5) C22 C24 C23 112.6(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C14 1.491(4) N2 C5 1.468(4) N2 C10 1.265(4) C3 N6 1.358(4) C3 C7 1.402(4) C3 C10 1.488(4) O4 C11 1.257(4) C5 C13 1.529(5) C5 C16 1.514(5) N6 C17 1.317(4) C7 C9 1.397(4) C7 C11 1.515(4) O8 C11 1.245(4) C9 C15 1.371(5) C12 C13 1.534(4) C12 C18 1.506(5) C14 C20 1.511(5) C14 C21 1.509(5) C15 C17 1.398(5) C16 C19 1.541(5) C18 C19 1.528(5) C20 C22 1.537(6) C21 C23 1.568(7) C22 C24 1.452(8) C23 C24 1.498(9)