#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238836.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_2238836 loop_ _publ_author_name 'Kanchanadevi, Jeevanandam' 'Anbalagan, Gopalakrishnan' 'Kannan, Damodharan' 'Bakthadoss, Manickam' 'Manivannan, Vadivelu' _publ_section_title ; 16-Methyl-11-(2-methylphenyl)-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.0^2,7^.0^13,17^]heptadeca-2(7),3,5,13(17),15-pentaene-10-carbonitrile ; _journal_coeditor_code BT6941 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1746 _journal_paper_doi 10.1107/S1600536813029905 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C28 H23 N3 O2' _chemical_formula_moiety 'C28 H23 N3 O2' _chemical_formula_sum 'C28 H23 N3 O2' _chemical_formula_weight 433.49 _chemical_name_systematic 16-Methyl-11-(2-methylphenyl)-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.0^2,7^.0^13,17^]heptadeca-2(7),3,5,13(17),15-pentaene-10-carbonitrile _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 72.720(5) _cell_angle_beta 76.997(5) _cell_angle_gamma 63.875(5) _cell_formula_units_Z 2 _cell_length_a 9.021(5) _cell_length_b 9.604(5) _cell_length_c 15.254(5) _cell_measurement_reflns_used 9100 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 25.4 _cell_measurement_theta_min 2.42 _cell_volume 1126.1(9) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f' _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 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 20066 _diffrn_reflns_theta_full 25.44 _diffrn_reflns_theta_max 25.44 _diffrn_reflns_theta_min 2.42 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.408 _refine_diff_density_min -0.182 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 4154 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0431 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.2260P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.1328 _reflns_number_gt 3085 _reflns_number_total 4154 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL KANCHANADEVI2782 in P-1 CELL 0.71073 9.0210 9.6040 15.2540 72.720 76.997 63.875 ZERR 2.00 0.0050 0.0050 0.0050 0.005 0.005 0.005 LATT 1 SFAC C H N O UNIT 56 46 6 4 MERG 2 FMAP 2 PLAN 25 OMIT 0 0 1 ACTA BOND $H CONF EQIV $1 -X, -Y, 2-Z HTAB C16 O2_$1 HTAB C2 N1 HTAB C6 O1 HTAB C28 O2 L.S. 4 WGHT 0.070900 0.226000 FVAR 0.72532 C1 1 0.692525 -0.076526 0.564885 11.00000 0.03713 0.04320 = 0.03687 -0.00761 0.00054 -0.01181 C2 1 0.839833 -0.074543 0.514205 11.00000 0.05144 0.07293 = 0.06316 -0.02748 0.01936 -0.02945 AFIX 43 H2 2 0.878813 -0.001770 0.517978 11.00000 -1.20000 AFIX 0 C3 1 0.928307 -0.179966 0.458408 11.00000 0.05976 0.08655 = 0.06428 -0.03107 0.02324 -0.02653 AFIX 43 H3 2 1.027914 -0.179103 0.425026 11.00000 -1.20000 AFIX 0 C4 1 0.871554 -0.286009 0.451440 11.00000 0.06963 0.07418 = 0.04878 -0.02749 0.00420 -0.01292 AFIX 43 H4 2 0.932373 -0.357723 0.413826 11.00000 -1.20000 AFIX 0 C5 1 0.723815 -0.286076 0.500423 11.00000 0.07091 0.06002 = 0.05325 -0.02085 -0.00672 -0.02121 AFIX 43 H5 2 0.683968 -0.357200 0.495083 11.00000 -1.20000 AFIX 0 C6 1 0.633427 -0.181171 0.557773 11.00000 0.04436 0.05357 = 0.04446 -0.01171 -0.00109 -0.01659 AFIX 43 H6 2 0.533727 -0.182025 0.591015 11.00000 -1.20000 AFIX 0 C7 1 0.488145 0.036335 0.694592 11.00000 0.03061 0.03614 = 0.04027 -0.00576 0.00102 -0.01564 C8 1 0.286224 -0.039000 0.794505 11.00000 0.02751 0.03825 = 0.03587 -0.00808 0.00158 -0.01316 AFIX 13 H8 2 0.191793 0.042699 0.761790 11.00000 -1.20000 AFIX 0 C9 1 0.249617 -0.184701 0.836665 11.00000 0.03658 0.04121 = 0.03443 -0.01090 0.00162 -0.01966 C10 1 0.374095 -0.325551 0.876186 11.00000 0.03999 0.04181 = 0.05206 -0.01060 -0.00411 -0.01825 AFIX 43 H10 2 0.480116 -0.329290 0.872268 11.00000 -1.20000 AFIX 0 C11 1 0.344164 -0.459336 0.920890 11.00000 0.05766 0.03862 = 0.05530 -0.00858 -0.00696 -0.01968 AFIX 43 H11 2 0.429277 -0.552672 0.946323 11.00000 -1.20000 AFIX 0 C12 1 0.186946 -0.453735 0.927621 11.00000 0.06880 0.04946 = 0.04828 -0.01038 0.00317 -0.03827 AFIX 43 H12 2 0.164003 -0.542062 0.959798 11.00000 -1.20000 AFIX 0 C13 1 0.064506 -0.317349 0.886666 11.00000 0.05163 0.06255 = 0.04799 -0.01705 0.00392 -0.03723 AFIX 43 H13 2 -0.040391 -0.316030 0.890305 11.00000 -1.20000 AFIX 0 C14 1 0.091286 -0.180939 0.839897 11.00000 0.04107 0.05190 = 0.03835 -0.01278 -0.00002 -0.02522 C15 1 0.315592 0.033438 0.865010 11.00000 0.03008 0.03734 = 0.03638 -0.00808 -0.00230 -0.01300 C16 1 0.175633 0.061622 0.944256 11.00000 0.03816 0.04792 = 0.03905 -0.01080 -0.00091 -0.01609 AFIX 23 H16A 2 0.172367 -0.039583 0.979311 11.00000 -1.20000 H16B 2 0.197563 0.108769 0.985370 11.00000 -1.20000 AFIX 0 C17 1 0.013515 0.300224 0.845812 11.00000 0.03713 0.04832 = 0.04189 -0.01537 -0.00205 -0.01216 C18 1 -0.144325 0.415901 0.829102 11.00000 0.03550 0.07068 = 0.06030 -0.02206 -0.00230 -0.00673 AFIX 43 H18 2 -0.237368 0.400798 0.863525 11.00000 -1.20000 AFIX 0 C19 1 -0.163130 0.551673 0.762269 11.00000 0.04803 0.06582 = 0.06275 -0.01859 -0.01329 0.00319 AFIX 43 H19 2 -0.268924 0.628726 0.750880 11.00000 -1.20000 AFIX 0 C20 1 -0.026149 0.574399 0.711985 11.00000 0.06550 0.04552 = 0.05307 -0.00851 -0.01269 -0.00263 AFIX 43 H20 2 -0.038763 0.667001 0.666516 11.00000 -1.20000 AFIX 0 C21 1 0.130407 0.459863 0.728855 11.00000 0.05043 0.04274 = 0.04648 -0.01199 -0.00329 -0.01248 AFIX 43 H21 2 0.222589 0.476676 0.694409 11.00000 -1.20000 AFIX 0 C22 1 0.154034 0.319998 0.795967 11.00000 0.03797 0.03863 = 0.03911 -0.01511 -0.00271 -0.01151 C23 1 0.327427 0.194509 0.814042 11.00000 0.03240 0.03769 = 0.04078 -0.01204 -0.00211 -0.01425 AFIX 13 H23 2 0.372440 0.226291 0.853991 11.00000 -1.20000 AFIX 0 C24 1 0.448211 0.165084 0.729597 11.00000 0.03249 0.03787 = 0.04455 -0.01002 0.00106 -0.01530 C25 1 0.554465 0.237095 0.674787 11.00000 0.04079 0.04477 = 0.05817 -0.01290 0.00471 -0.02217 C26 1 0.573321 0.379934 0.683363 11.00000 0.07669 0.06689 = 0.09840 -0.03088 0.01896 -0.04932 AFIX 137 H26A 2 0.685950 0.368793 0.663181 11.00000 -1.50000 H26B 2 0.546209 0.388325 0.746675 11.00000 -1.50000 H26C 2 0.499872 0.474101 0.645721 11.00000 -1.50000 AFIX 0 C27 1 0.470956 -0.073930 0.906464 11.00000 0.03851 0.04105 = 0.04350 -0.01113 -0.00296 -0.01788 C28 1 -0.048540 -0.038284 0.793482 11.00000 0.04560 0.07359 = 0.06641 -0.00664 -0.01315 -0.02994 AFIX 137 H28A 2 -0.144707 -0.061995 0.803462 11.00000 -1.50000 H28B 2 -0.015306 -0.012988 0.728393 11.00000 -1.50000 H28C 2 -0.074638 0.050967 0.819038 11.00000 -1.50000 AFIX 0 N1 3 0.649175 0.160672 0.610129 11.00000 0.04516 0.05050 = 0.06000 -0.01482 0.01246 -0.02781 N2 3 0.607095 0.033542 0.622556 11.00000 0.03727 0.04230 = 0.04478 -0.01138 0.00831 -0.01896 N3 3 0.589891 -0.154116 0.940373 11.00000 0.05093 0.05161 = 0.07441 -0.01082 -0.02220 -0.01587 O1 4 0.431309 -0.080651 0.726752 11.00000 0.03747 0.03999 = 0.04204 -0.01333 0.00741 -0.01943 O2 4 0.019399 0.163714 0.910925 11.00000 0.03228 0.05687 = 0.05255 -0.01182 0.00357 -0.01610 HKLF 4 REM KANCHANADEVI2782 in P-1 REM R1 = 0.0431 for 3085 Fo > 4sig(Fo) and 0.0627 for all 4154 data REM 300 parameters refined using 0 restraints END WGHT 0.0603 0.2669 REM Highest difference peak 0.408, deepest hole -0.182, 1-sigma level 0.039 Q1 1 0.2884 0.7018 0.5858 11.00000 0.05 0.41 Q2 1 0.4766 0.4471 0.7170 11.00000 0.05 0.21 Q3 1 0.6311 0.4310 0.6311 11.00000 0.05 0.17 Q4 1 -0.0232 0.0641 0.7618 11.00000 0.05 0.17 Q5 1 0.2996 -0.0006 0.8350 11.00000 0.05 0.15 Q6 1 0.2119 0.0777 0.7466 11.00000 0.05 0.14 Q7 1 -0.1047 -0.0862 0.7516 11.00000 0.05 0.14 Q8 1 0.2376 0.2571 0.8006 11.00000 0.05 0.12 Q9 1 0.1554 -0.1590 0.8598 11.00000 0.05 0.12 Q10 1 0.4580 0.2402 0.6932 11.00000 0.05 0.12 Q11 1 0.1856 -0.1924 0.8108 11.00000 0.05 0.12 Q12 1 0.1032 0.2854 0.7969 11.00000 0.05 0.12 Q13 1 -0.2343 0.3097 0.8923 11.00000 0.05 0.12 Q14 1 0.4053 0.1849 0.7630 11.00000 0.05 0.12 Q15 1 0.1389 -0.4047 0.8742 11.00000 0.05 0.11 Q16 1 0.4834 -0.5416 0.9656 11.00000 0.05 0.11 Q17 1 0.6833 0.3037 0.7462 11.00000 0.05 0.11 Q18 1 -0.1808 -0.0065 0.8503 11.00000 0.05 0.11 Q19 1 0.6793 0.2357 0.5560 11.00000 0.05 0.11 Q20 1 0.3263 0.1042 0.8404 11.00000 0.05 0.11 Q21 1 0.4088 0.1459 0.6982 11.00000 0.05 0.11 Q22 1 0.5648 0.2958 0.6834 11.00000 0.05 0.11 Q23 1 0.2489 -0.4178 0.9518 11.00000 0.05 0.10 Q24 1 0.2612 -0.1173 0.8270 11.00000 0.05 0.10 Q25 1 0.2596 0.4725 0.6455 11.00000 0.05 0.10 ; _cod_data_source_file bt6941.cif _cod_data_source_block I _cod_database_code 2238836 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_symmetry_multiplicity C C1 0.6925(2) -0.0765(2) 0.56488(12) 0.0419(4) Uani d . 1 1 C C2 0.8398(3) -0.0745(3) 0.51420(15) 0.0625(6) Uani d . 1 1 H H2 0.8788 -0.0018 0.5180 0.075 Uiso calc R 1 1 C C3 0.9283(3) -0.1800(3) 0.45841(16) 0.0732(7) Uani d . 1 1 H H3 1.0279 -0.1791 0.4250 0.088 Uiso calc R 1 1 C C4 0.8716(3) -0.2860(3) 0.45144(15) 0.0688(6) Uani d . 1 1 H H4 0.9324 -0.3577 0.4138 0.083 Uiso calc R 1 1 C C5 0.7238(3) -0.2861(3) 0.50042(14) 0.0614(6) Uani d . 1 1 H H5 0.6840 -0.3572 0.4951 0.074 Uiso calc R 1 1 C C6 0.6334(2) -0.1812(2) 0.55777(13) 0.0491(5) Uani d . 1 1 H H6 0.5337 -0.1820 0.5910 0.059 Uiso calc R 1 1 C C7 0.4881(2) 0.0363(2) 0.69459(11) 0.0364(4) Uani d . 1 1 C C8 0.28622(19) -0.0390(2) 0.79451(11) 0.0349(4) Uani d . 1 1 H H8 0.1918 0.0427 0.7618 0.042 Uiso calc R 1 1 C C9 0.2496(2) -0.1847(2) 0.83666(11) 0.0363(4) Uani d . 1 1 C C10 0.3741(2) -0.3256(2) 0.87619(13) 0.0441(4) Uani d . 1 1 H H10 0.4801 -0.3293 0.8723 0.053 Uiso calc R 1 1 C C11 0.3442(3) -0.4593(2) 0.92089(13) 0.0507(5) Uani d . 1 1 H H11 0.4293 -0.5527 0.9463 0.061 Uiso calc R 1 1 C C12 0.1869(3) -0.4537(2) 0.92762(13) 0.0519(5) Uani d . 1 1 H H12 0.1640 -0.5421 0.9598 0.062 Uiso calc R 1 1 C C13 0.0645(2) -0.3173(2) 0.88667(13) 0.0493(5) Uani d . 1 1 H H13 -0.0404 -0.3160 0.8903 0.059 Uiso calc R 1 1 C C14 0.0913(2) -0.1809(2) 0.83990(12) 0.0415(4) Uani d . 1 1 C C15 0.31559(19) 0.03344(19) 0.86501(11) 0.0351(4) Uani d . 1 1 C C16 0.1756(2) 0.0616(2) 0.94426(12) 0.0425(4) Uani d . 1 1 H H16A 0.1724 -0.0396 0.9793 0.051 Uiso calc R 1 1 H H16B 0.1976 0.1088 0.9854 0.051 Uiso calc R 1 1 C C17 0.0135(2) 0.3002(2) 0.84581(12) 0.0435(4) Uani d . 1 1 C C18 -0.1443(2) 0.4159(3) 0.82910(15) 0.0598(6) Uani d . 1 1 H H18 -0.2374 0.4008 0.8635 0.072 Uiso calc R 1 1 C C19 -0.1631(3) 0.5517(3) 0.76227(16) 0.0664(6) Uani d . 1 1 H H19 -0.2689 0.6287 0.7509 0.080 Uiso calc R 1 1 C C20 -0.0261(3) 0.5744(2) 0.71199(15) 0.0616(6) Uani d . 1 1 H H20 -0.0388 0.6670 0.6665 0.074 Uiso calc R 1 1 C C21 0.1304(2) 0.4599(2) 0.72885(13) 0.0488(5) Uani d . 1 1 H H21 0.2226 0.4767 0.6944 0.059 Uiso calc R 1 1 C C22 0.1540(2) 0.3200(2) 0.79597(12) 0.0388(4) Uani d . 1 1 C C23 0.3274(2) 0.19451(19) 0.81404(11) 0.0365(4) Uani d . 1 1 H H23 0.3724 0.2263 0.8540 0.044 Uiso calc R 1 1 C C24 0.4482(2) 0.1651(2) 0.72960(12) 0.0386(4) Uani d . 1 1 C C25 0.5545(2) 0.2371(2) 0.67479(14) 0.0475(5) Uani d . 1 1 C C26 0.5733(3) 0.3799(3) 0.68336(19) 0.0751(7) Uani d . 1 1 H H26A 0.6859 0.3688 0.6632 0.113 Uiso calc R 1 1 H H26B 0.5462 0.3883 0.7467 0.113 Uiso calc R 1 1 H H26C 0.4999 0.4741 0.6457 0.113 Uiso calc R 1 1 C C27 0.4710(2) -0.0739(2) 0.90646(12) 0.0402(4) Uani d . 1 1 C C28 -0.0485(2) -0.0383(3) 0.79348(15) 0.0606(6) Uani d . 1 1 H H28A -0.1447 -0.0620 0.8035 0.091 Uiso calc R 1 1 H H28B -0.0153 -0.0130 0.7284 0.091 Uiso calc R 1 1 H H28C -0.0746 0.0510 0.8190 0.091 Uiso calc R 1 1 N N1 0.64918(19) 0.16067(19) 0.61013(11) 0.0513(4) Uani d . 1 1 N N2 0.60710(17) 0.03354(17) 0.62256(10) 0.0422(4) Uani d . 1 1 N N3 0.5899(2) -0.1541(2) 0.94037(13) 0.0589(5) Uani d . 1 1 O O1 0.43131(14) -0.08065(13) 0.72675(8) 0.0395(3) Uani d . 1 1 O O2 0.01940(14) 0.16371(16) 0.91092(9) 0.0495(3) Uani d . 1 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 C1 0.0371(9) 0.0432(10) 0.0369(9) -0.0118(8) 0.0005(7) -0.0076(8) C2 0.0514(12) 0.0729(15) 0.0632(14) -0.0294(11) 0.0194(10) -0.0275(12) C3 0.0598(14) 0.0866(17) 0.0643(15) -0.0265(13) 0.0232(11) -0.0311(13) C4 0.0696(15) 0.0742(16) 0.0488(12) -0.0129(13) 0.0042(11) -0.0275(11) C5 0.0709(15) 0.0600(13) 0.0532(12) -0.0212(11) -0.0067(11) -0.0209(10) C6 0.0444(11) 0.0536(12) 0.0445(11) -0.0166(9) -0.0011(8) -0.0117(9) C7 0.0306(8) 0.0361(9) 0.0403(9) -0.0156(7) 0.0010(7) -0.0058(7) C8 0.0275(8) 0.0383(9) 0.0359(9) -0.0132(7) 0.0016(7) -0.0081(7) C9 0.0366(9) 0.0412(10) 0.0344(9) -0.0197(8) 0.0016(7) -0.0109(7) C10 0.0400(10) 0.0418(10) 0.0521(11) -0.0182(8) -0.0041(8) -0.0106(8) C11 0.0577(12) 0.0386(10) 0.0553(12) -0.0197(9) -0.0070(9) -0.0086(9) C12 0.0688(14) 0.0495(12) 0.0483(11) -0.0383(11) 0.0032(10) -0.0104(9) C13 0.0516(11) 0.0625(13) 0.0480(11) -0.0372(11) 0.0039(9) -0.0171(10) C14 0.0411(10) 0.0519(11) 0.0384(9) -0.0252(9) 0.0000(7) -0.0128(8) C15 0.0301(8) 0.0373(9) 0.0364(9) -0.0130(7) -0.0023(7) -0.0081(7) C16 0.0382(10) 0.0479(10) 0.0391(10) -0.0161(8) -0.0009(7) -0.0108(8) C17 0.0371(10) 0.0483(11) 0.0419(10) -0.0122(8) -0.0021(8) -0.0154(8) C18 0.0355(10) 0.0707(15) 0.0603(13) -0.0067(10) -0.0023(9) -0.0221(11) C19 0.0480(13) 0.0658(15) 0.0627(14) 0.0032(11) -0.0133(11) -0.0186(12) C20 0.0655(14) 0.0455(12) 0.0531(12) -0.0026(10) -0.0127(11) -0.0085(9) C21 0.0504(11) 0.0427(11) 0.0465(11) -0.0125(9) -0.0033(9) -0.0120(9) C22 0.0380(9) 0.0386(10) 0.0391(9) -0.0115(8) -0.0027(7) -0.0151(8) C23 0.0324(9) 0.0377(9) 0.0408(9) -0.0142(8) -0.0021(7) -0.0120(7) C24 0.0325(9) 0.0379(10) 0.0446(10) -0.0153(8) 0.0011(7) -0.0100(8) C25 0.0408(10) 0.0448(11) 0.0582(12) -0.0222(9) 0.0047(9) -0.0129(9) C26 0.0767(16) 0.0669(15) 0.0984(19) -0.0493(13) 0.0190(14) -0.0309(14) C27 0.0385(10) 0.0411(10) 0.0435(10) -0.0179(9) -0.0030(8) -0.0111(8) C28 0.0456(12) 0.0736(15) 0.0664(14) -0.0299(11) -0.0131(10) -0.0066(11) N1 0.0452(9) 0.0505(10) 0.0600(10) -0.0278(8) 0.0125(8) -0.0148(8) N2 0.0373(8) 0.0423(8) 0.0448(8) -0.0190(7) 0.0083(6) -0.0114(7) N3 0.0509(10) 0.0516(10) 0.0744(12) -0.0159(9) -0.0222(9) -0.0108(9) O1 0.0375(6) 0.0400(7) 0.0420(7) -0.0194(5) 0.0074(5) -0.0133(5) O2 0.0323(7) 0.0569(8) 0.0525(8) -0.0161(6) 0.0036(6) -0.0118(6) 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 C6 C1 C2 120.00(18) C6 C1 N2 122.32(16) C2 C1 N2 117.68(17) C3 C2 C1 120.0(2) C3 C2 H2 120.0 C1 C2 H2 120.0 C4 C3 C2 120.6(2) C4 C3 H3 119.7 C2 C3 H3 119.7 C3 C4 C5 119.5(2) C3 C4 H4 120.3 C5 C4 H4 120.3 C4 C5 C6 120.7(2) C4 C5 H5 119.7 C6 C5 H5 119.7 C1 C6 C5 119.27(19) C1 C6 H6 120.4 C5 C6 H6 120.4 N2 C7 O1 122.29(15) N2 C7 C24 109.30(15) O1 C7 C24 128.28(15) O1 C8 C9 107.74(13) O1 C8 C15 109.91(13) C9 C8 C15 114.90(14) O1 C8 H8 108.0 C9 C8 H8 108.0 C15 C8 H8 108.0 C10 C9 C14 119.09(16) C10 C9 C8 119.30(15) C14 C9 C8 121.58(15) C11 C10 C9 121.61(17) C11 C10 H10 119.2 C9 C10 H10 119.2 C10 C11 C12 119.34(18) C10 C11 H11 120.3 C12 C11 H11 120.3 C13 C12 C11 119.63(18) C13 C12 H12 120.2 C11 C12 H12 120.2 C12 C13 C14 122.41(17) C12 C13 H13 118.8 C14 C13 H13 118.8 C13 C14 C9 117.83(17) C13 C14 C28 118.88(16) C9 C14 C28 123.28(16) C27 C15 C16 107.11(14) C27 C15 C23 108.72(13) C16 C15 C23 108.72(14) C27 C15 C8 110.90(14) C16 C15 C8 112.16(13) C23 C15 C8 109.13(14) O2 C16 C15 111.34(14) O2 C16 H16A 109.4 C15 C16 H16A 109.4 O2 C16 H16B 109.4 C15 C16 H16B 109.4 H16A C16 H16B 108.0 O2 C17 C22 123.01(16) O2 C17 C18 115.77(17) C22 C17 C18 121.14(19) C19 C18 C17 120.1(2) C19 C18 H18 119.9 C17 C18 H18 119.9 C18 C19 C20 120.0(2) C18 C19 H19 120.0 C20 C19 H19 120.0 C19 C20 C21 119.9(2) C19 C20 H20 120.1 C21 C20 H20 120.1 C20 C21 C22 121.67(19) C20 C21 H21 119.2 C22 C21 H21 119.2 C17 C22 C21 117.23(17) C17 C22 C23 121.57(16) C21 C22 C23 121.20(16) C24 C23 C22 115.21(14) C24 C23 C15 106.57(13) C22 C23 C15 108.94(13) C24 C23 H23 108.7 C22 C23 H23 108.7 C15 C23 H23 108.7 C7 C24 C25 103.93(15) C7 C24 C23 121.78(15) C25 C24 C23 134.00(16) N1 C25 C24 111.93(16) N1 C25 C26 119.44(17) C24 C25 C26 128.61(18) C25 C26 H26A 109.5 C25 C26 H26B 109.5 H26A C26 H26B 109.5 C25 C26 H26C 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 N3 C27 C15 177.91(19) C14 C28 H28A 109.5 C14 C28 H28B 109.5 H28A C28 H28B 109.5 C14 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C25 N1 N2 105.44(14) C7 N2 N1 109.38(14) C7 N2 C1 131.23(15) N1 N2 C1 119.35(14) C7 O1 C8 111.93(12) C17 O2 C16 116.17(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C6 1.367(3) C1 C2 1.384(3) C1 N2 1.420(2) C2 C3 1.372(3) C2 H2 0.9300 C3 C4 1.363(3) C3 H3 0.9300 C4 C5 1.374(3) C4 H4 0.9300 C5 C6 1.387(3) C5 H5 0.9300 C6 H6 0.9300 C7 N2 1.349(2) C7 O1 1.354(2) C7 C24 1.363(2) C8 O1 1.4550(19) C8 C9 1.502(2) C8 C15 1.564(2) C8 H8 0.9800 C9 C10 1.392(3) C9 C14 1.403(2) C10 C11 1.375(3) C10 H10 0.9300 C11 C12 1.377(3) C11 H11 0.9300 C12 C13 1.370(3) C12 H12 0.9300 C13 C14 1.389(3) C13 H13 0.9300 C14 C28 1.508(3) C15 C27 1.472(2) C15 C16 1.528(2) C15 C23 1.550(2) C16 O2 1.420(2) C16 H16A 0.9700 C16 H16B 0.9700 C17 O2 1.377(2) C17 C22 1.383(3) C17 C18 1.389(3) C18 C19 1.364(3) C18 H18 0.9300 C19 C20 1.369(3) C19 H19 0.9300 C20 C21 1.378(3) C20 H20 0.9300 C21 C22 1.388(3) C21 H21 0.9300 C22 C23 1.520(2) C23 C24 1.497(2) C23 H23 0.9800 C24 C25 1.406(2) C25 N1 1.319(2) C25 C26 1.500(3) C26 H26A 0.9600 C26 H26B 0.9600 C26 H26C 0.9600 C27 N3 1.139(2) C28 H28A 0.9600 C28 H28B 0.9600 C28 H28C 0.9600 N1 N2 1.382(2) 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 C2 H2 N1 . 0.93 2.42 2.759(3) 101.5 C6 H6 O1 . 0.93 2.37 2.952(2) 120.1 C28 H28C O2 . 0.96 2.47 3.310(3) 146.0 C16 H16A O2 2_557 0.97 2.56 3.380(2) 142.5 C20 H20 Cg1 1_465 0.96 2.86 3.567 134 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 C6 C1 C2 C3 -1.4(3) N2 C1 C2 C3 179.1(2) C1 C2 C3 C4 0.8(4) C2 C3 C4 C5 0.4(4) C3 C4 C5 C6 -1.0(4) C2 C1 C6 C5 0.9(3) N2 C1 C6 C5 -179.67(17) C4 C5 C6 C1 0.3(3) O1 C8 C9 C10 54.68(19) C15 C8 C9 C10 -68.2(2) O1 C8 C9 C14 -127.45(16) C15 C8 C9 C14 109.68(17) C14 C9 C10 C11 -2.2(3) C8 C9 C10 C11 175.76(16) C9 C10 C11 C12 -0.6(3) C10 C11 C12 C13 2.6(3) C11 C12 C13 C14 -1.7(3) C12 C13 C14 C9 -1.1(3) C12 C13 C14 C28 177.50(18) C10 C9 C14 C13 3.0(2) C8 C9 C14 C13 -174.90(15) C10 C9 C14 C28 -175.56(17) C8 C9 C14 C28 6.6(3) O1 C8 C15 C27 -53.68(18) C9 C8 C15 C27 68.02(18) O1 C8 C15 C16 -173.39(13) C9 C8 C15 C16 -51.69(19) O1 C8 C15 C23 66.07(16) C9 C8 C15 C23 -172.23(13) C27 C15 C16 O2 -179.60(14) C23 C15 C16 O2 63.08(17) C8 C15 C16 O2 -57.70(19) O2 C17 C18 C19 -176.47(18) C22 C17 C18 C19 0.3(3) C17 C18 C19 C20 -0.4(3) C18 C19 C20 C21 0.2(3) C19 C20 C21 C22 0.2(3) O2 C17 C22 C21 176.57(15) C18 C17 C22 C21 0.0(3) O2 C17 C22 C23 -3.8(3) C18 C17 C22 C23 179.67(16) C20 C21 C22 C17 -0.3(3) C20 C21 C22 C23 -179.94(17) C17 C22 C23 C24 139.64(17) C21 C22 C23 C24 -40.7(2) C17 C22 C23 C15 20.0(2) C21 C22 C23 C15 -160.35(15) C27 C15 C23 C24 71.73(17) C16 C15 C23 C24 -171.97(13) C8 C15 C23 C24 -49.35(16) C27 C15 C23 C22 -163.39(13) C16 C15 C23 C22 -47.10(17) C8 C15 C23 C22 75.53(16) N2 C7 C24 C25 -1.34(19) O1 C7 C24 C25 174.53(17) N2 C7 C24 C23 -175.98(15) O1 C7 C24 C23 -0.1(3) C22 C23 C24 C7 -101.70(19) C15 C23 C24 C7 19.3(2) C22 C23 C24 C25 85.5(2) C15 C23 C24 C25 -153.51(19) C7 C24 C25 N1 1.3(2) C23 C24 C25 N1 174.98(18) C7 C24 C25 C26 -176.9(2) C23 C24 C25 C26 -3.3(4) C24 C25 N1 N2 -0.8(2) C26 C25 N1 N2 177.66(18) O1 C7 N2 N1 -175.21(15) C24 C7 N2 N1 0.96(19) O1 C7 N2 C1 2.1(3) C24 C7 N2 C1 178.30(17) C25 N1 N2 C7 -0.1(2) C25 N1 N2 C1 -177.82(16) C6 C1 N2 C7 18.8(3) C2 C1 N2 C7 -161.74(19) C6 C1 N2 N1 -164.07(17) C2 C1 N2 N1 15.4(3) N2 C7 O1 C8 -170.88(15) C24 C7 O1 C8 13.7(2) C9 C8 O1 C7 -171.15(13) C15 C8 O1 C7 -45.26(17) C22 C17 O2 C16 17.4(2) C18 C17 O2 C16 -165.84(16) C15 C16 O2 C17 -47.30(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086187