#------------------------------------------------------------------------------ #$Date: 2026-04-23 02:02:33 +0100 (Thu, 23 Apr 2026) $ #$Revision: 305600 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064384.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_7064384 loop_ _publ_author_name 'Khatua, Snehadrinarayan' 'Lyngkhoi, Deikrisha Lyngdoh' 'Baruah, Khanindram' 'Patra, Sumit Kumar' _publ_section_title ; Seven-membered Heterocycle Containing Coumarin-Based Probe for Selective Detection of Chemical Warfare Agent Phosgene in Solution and Gas Phase ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ00818F _journal_year 2026 _chemical_formula_sum 'C17 H16 N2 O3' _chemical_formula_weight 296.32 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2025-03-28 deposited with the CCDC. 2026-04-21 downloaded from the CCDC. ; _cell_angle_alpha 71.346(8) _cell_angle_beta 88.560(7) _cell_angle_gamma 83.085(7) _cell_formula_units_Z 2 _cell_length_a 7.5973(6) _cell_length_b 8.5961(8) _cell_length_c 11.7834(11) _cell_measurement_reflns_used 1567 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.385 _cell_measurement_theta_min 3.124 _cell_volume 723.74(12) _computing_cell_refinement 'CrysAlis PRO' _computing_data_collection 'CrysAlis PRO (Agilent, 2013)' _computing_data_reduction 'CrysAlis PRO' _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 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4588 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 3.238 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour plate _exptl_crystal_density_diffrn 1.360 _exptl_crystal_description colorless _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.070 _refine_diff_density_max 0.213 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2951 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0490 _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^)+(0.0549P)^2^+0.1482P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1130 _refine_ls_wR_factor_ref 0.1238 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2243 _reflns_number_total 2951 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00818f2.cif _cod_data_source_block shelx _cod_database_code 7064384 _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 0.979 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL sk-sp-118_a.res in P-1 shelx.res created by SHELXL-2018/3 at 17:11:43 on 28-Mar-2025 CELL 0.71073 7.5973 8.5961 11.7834 71.346 88.560 83.085 ZERR 2.00 0.0006 0.0008 0.0011 0.008 0.007 0.007 LATT 1 SFAC C H N O UNIT 34 32 4 6 MERG 2 MORE -1 SHEL 100 0.8 FMAP 2 PLAN 5 SIZE 0.070 0.120 0.230 ACTA 52.00 BOND $H CONF LIST 4 L.S. 80 TEMP 20.00 WGHT 0.054900 0.148200 FVAR 16.78859 C1 1 0.728236 0.658766 0.571934 11.00000 0.02836 0.04339 = 0.04616 -0.01546 0.00438 -0.00561 C2 1 0.512930 0.842032 0.434443 11.00000 0.03500 0.03915 = 0.03223 -0.01467 0.00477 -0.00838 C3 1 0.485425 0.979369 0.332934 11.00000 0.05457 0.04577 = 0.03523 -0.00885 0.01038 -0.01628 AFIX 43 H3 2 0.581139 1.026857 0.290883 11.00000 -1.20000 AFIX 0 C4 1 0.315000 1.044347 0.295306 11.00000 0.06842 0.03983 = 0.03399 -0.00198 -0.00185 -0.00577 AFIX 43 H4 2 0.294614 1.137323 0.227822 11.00000 -1.20000 AFIX 0 C5 1 0.172975 0.971609 0.357744 11.00000 0.04711 0.04828 = 0.04391 -0.00836 -0.00797 -0.00083 AFIX 43 H5 2 0.057618 1.017137 0.332689 11.00000 -1.20000 AFIX 0 C6 1 0.201885 0.832577 0.456463 11.00000 0.03487 0.04353 = 0.03754 -0.00713 -0.00158 -0.00688 AFIX 43 H6 2 0.105447 0.784257 0.496822 11.00000 -1.20000 AFIX 0 C7 1 0.373947 0.762449 0.497308 11.00000 0.03267 0.03379 = 0.02856 -0.01262 0.00250 -0.00726 C8 1 0.417244 0.615784 0.601905 11.00000 0.02754 0.03408 = 0.02808 -0.01277 0.00331 -0.00634 C9 1 0.591015 0.573646 0.640466 11.00000 0.02535 0.03788 = 0.03492 -0.01273 0.00215 -0.00503 C10 1 0.654251 0.439619 0.753315 11.00000 0.02641 0.04705 = 0.04300 -0.00999 -0.00164 -0.00221 AFIX 23 H10A 2 0.674530 0.335090 0.737254 11.00000 -1.20000 H10B 2 0.766461 0.462397 0.778239 11.00000 -1.20000 AFIX 0 C11 1 0.270894 0.384562 0.749262 11.00000 0.02620 0.03248 = 0.03155 -0.00948 0.00576 -0.00326 C12 1 0.131074 0.293940 0.747942 11.00000 0.03127 0.04224 = 0.04357 -0.01512 0.00450 -0.00740 AFIX 43 H12 2 0.053569 0.327576 0.682454 11.00000 -1.20000 AFIX 0 C13 1 0.106741 0.155625 0.842328 11.00000 0.04330 0.04312 = 0.05863 -0.01161 0.01224 -0.01686 AFIX 43 H13 2 0.012165 0.096881 0.840914 11.00000 -1.20000 AFIX 0 C14 1 0.221898 0.103402 0.939220 11.00000 0.05498 0.04003 = 0.05245 -0.00021 0.01380 -0.01026 AFIX 43 H14 2 0.205390 0.009373 1.002996 11.00000 -1.20000 AFIX 0 C15 1 0.361395 0.190787 0.941339 11.00000 0.04545 0.04062 = 0.03658 -0.00380 0.00300 0.00003 AFIX 43 H15 2 0.439145 0.154966 1.006740 11.00000 -1.20000 AFIX 0 C16 1 0.387627 0.332136 0.846831 11.00000 0.03075 0.03297 = 0.03296 -0.01015 0.00438 -0.00080 C17 1 0.137584 0.681766 0.892487 11.00000 0.07791 0.10292 = 0.12631 -0.07139 -0.00765 0.01665 AFIX 137 H17A 2 0.120001 0.570243 0.937766 11.00000 -1.50000 H17B 2 0.101562 0.704375 0.810721 11.00000 -1.50000 H17C 2 0.068043 0.756944 0.925881 11.00000 -1.50000 AFIX 0 N1 3 0.527126 0.424716 0.851527 11.00000 0.03361 0.04213 = 0.03068 -0.00752 -0.00525 -0.00422 N2 3 0.278391 0.532765 0.653034 11.00000 0.02326 0.03911 = 0.03217 -0.00221 -0.00210 -0.00719 O1 4 0.886132 0.623191 0.596586 11.00000 0.02346 0.06658 = 0.07826 -0.00536 0.00440 -0.00647 O2 4 0.686475 0.788127 0.470072 11.00000 0.03205 0.04926 = 0.04241 -0.00927 0.00961 -0.01204 O3 4 0.315146 0.701570 0.896944 11.00000 0.08138 0.06224 = 0.07091 -0.03368 -0.01371 0.00451 H1N 2 0.586319 0.378169 0.921144 11.00000 0.04700 H2N 2 0.171767 0.572348 0.616737 11.00000 0.04673 H3O 2 0.386853 0.610740 0.872750 11.00000 0.11668 HKLF 4 REM sk-sp-118_a.res in P-1 REM wR2 = 0.1238, GooF = S = 1.026, Restrained GooF = 1.026 for all data REM R1 = 0.0490 for 2243 Fo > 4sig(Fo) and 0.0693 for all 2951 data REM 212 parameters refined using 0 restraints END WGHT 0.0548 0.1479 REM Highest difference peak 0.213, deepest hole -0.211, 1-sigma level 0.035 Q1 1 0.2491 0.6279 0.9509 11.00000 0.05 0.21 Q2 1 0.4464 0.8026 0.4757 11.00000 0.05 0.19 Q3 1 0.5243 0.5616 0.6120 11.00000 0.05 0.18 Q4 1 0.6381 0.6158 0.6048 11.00000 0.05 0.17 Q5 1 0.6186 0.5077 0.6884 11.00000 0.05 0.16 ; _shelx_res_checksum 58232 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.7282(2) 0.6588(2) 0.57193(16) 0.0390(4) Uani 1 1 d . . . . . C2 C 0.5129(2) 0.8420(2) 0.43444(15) 0.0344(4) Uani 1 1 d . . . . . C3 C 0.4854(3) 0.9794(2) 0.33293(16) 0.0454(5) Uani 1 1 d . . . . . H3 H 0.581139 1.026857 0.290883 0.055 Uiso 1 1 calc R U . . . C4 C 0.3150(3) 1.0443(2) 0.29531(17) 0.0498(5) Uani 1 1 d . . . . . H4 H 0.294614 1.137323 0.227822 0.060 Uiso 1 1 calc R U . . . C5 C 0.1730(3) 0.9716(2) 0.35774(17) 0.0482(5) Uani 1 1 d . . . . . H5 H 0.057618 1.017137 0.332689 0.058 Uiso 1 1 calc R U . . . C6 C 0.2019(2) 0.8326(2) 0.45646(16) 0.0398(4) Uani 1 1 d . . . . . H6 H 0.105447 0.784257 0.496822 0.048 Uiso 1 1 calc R U . . . C7 C 0.3739(2) 0.7624(2) 0.49731(14) 0.0308(4) Uani 1 1 d . . . . . C8 C 0.41724(19) 0.61578(19) 0.60191(14) 0.0290(4) Uani 1 1 d . . . . . C9 C 0.59101(19) 0.5736(2) 0.64047(14) 0.0324(4) Uani 1 1 d . . . . . C10 C 0.6543(2) 0.4396(2) 0.75331(16) 0.0400(4) Uani 1 1 d . . . . . H10A H 0.674530 0.335090 0.737254 0.048 Uiso 1 1 calc R U . . . H10B H 0.766461 0.462397 0.778239 0.048 Uiso 1 1 calc R U . . . C11 C 0.27089(19) 0.3846(2) 0.74926(14) 0.0304(4) Uani 1 1 d . . . . . C12 C 0.1311(2) 0.2939(2) 0.74794(16) 0.0385(4) Uani 1 1 d . . . . . H12 H 0.053569 0.327576 0.682454 0.046 Uiso 1 1 calc R U . . . C13 C 0.1067(2) 0.1556(2) 0.84233(18) 0.0487(5) Uani 1 1 d . . . . . H13 H 0.012165 0.096881 0.840914 0.058 Uiso 1 1 calc R U . . . C14 C 0.2219(3) 0.1034(2) 0.93922(19) 0.0525(5) Uani 1 1 d . . . . . H14 H 0.205390 0.009373 1.002996 0.063 Uiso 1 1 calc R U . . . C15 C 0.3614(2) 0.1908(2) 0.94134(16) 0.0434(5) Uani 1 1 d . . . . . H15 H 0.439145 0.154966 1.006740 0.052 Uiso 1 1 calc R U . . . C16 C 0.3876(2) 0.3321(2) 0.84683(14) 0.0326(4) Uani 1 1 d . . . . . C17 C 0.1376(4) 0.6818(4) 0.8925(3) 0.0962(10) Uani 1 1 d . . . . . H17A H 0.120001 0.570243 0.937766 0.144 Uiso 1 1 calc R U . . . H17B H 0.101562 0.704375 0.810721 0.144 Uiso 1 1 calc R U . . . H17C H 0.068043 0.756944 0.925881 0.144 Uiso 1 1 calc R U . . . N1 N 0.52713(18) 0.42472(18) 0.85153(13) 0.0364(4) Uani 1 1 d . . . . . N2 N 0.27839(17) 0.53276(17) 0.65303(12) 0.0334(3) Uani 1 1 d . . . . . O1 O 0.88613(15) 0.62319(18) 0.59659(14) 0.0603(4) Uani 1 1 d . . . . . O2 O 0.68647(14) 0.78813(15) 0.47007(11) 0.0421(3) Uani 1 1 d . . . . . O3 O 0.3151(2) 0.7016(2) 0.89694(15) 0.0694(5) Uani 1 1 d . . . . . H1N H 0.586(2) 0.378(2) 0.9211(19) 0.047(5) Uiso 1 1 d . . . . . H2N H 0.172(2) 0.572(2) 0.6167(17) 0.047(5) Uiso 1 1 d . . . . . H3O H 0.387(4) 0.611(4) 0.873(3) 0.117(11) 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 C1 0.0284(8) 0.0434(10) 0.0462(11) -0.0155(9) 0.0044(7) -0.0056(7) C2 0.0350(9) 0.0391(9) 0.0322(9) -0.0147(8) 0.0048(7) -0.0084(7) C3 0.0546(11) 0.0458(11) 0.0352(10) -0.0089(8) 0.0104(8) -0.0163(9) C4 0.0684(13) 0.0398(11) 0.0340(10) -0.0020(8) -0.0018(9) -0.0058(9) C5 0.0471(11) 0.0483(11) 0.0439(11) -0.0084(9) -0.0080(8) -0.0008(9) C6 0.0349(9) 0.0435(10) 0.0375(10) -0.0071(8) -0.0016(7) -0.0069(7) C7 0.0327(8) 0.0338(9) 0.0286(8) -0.0126(7) 0.0025(6) -0.0073(7) C8 0.0275(8) 0.0341(9) 0.0281(8) -0.0128(7) 0.0033(6) -0.0063(6) C9 0.0254(8) 0.0379(9) 0.0349(9) -0.0127(7) 0.0021(6) -0.0050(6) C10 0.0264(8) 0.0470(11) 0.0430(10) -0.0100(8) -0.0016(7) -0.0022(7) C11 0.0262(8) 0.0325(9) 0.0316(9) -0.0095(7) 0.0058(6) -0.0033(6) C12 0.0313(9) 0.0422(10) 0.0436(10) -0.0151(8) 0.0045(7) -0.0074(7) C13 0.0433(10) 0.0431(11) 0.0586(13) -0.0116(9) 0.0122(9) -0.0169(8) C14 0.0550(12) 0.0400(11) 0.0525(12) -0.0002(9) 0.0138(10) -0.0103(9) C15 0.0455(10) 0.0406(10) 0.0366(10) -0.0038(8) 0.0030(8) 0.0000(8) C16 0.0307(8) 0.0330(9) 0.0330(9) -0.0101(7) 0.0044(7) -0.0008(7) C17 0.0779(19) 0.103(2) 0.126(3) -0.071(2) -0.0077(17) 0.0167(16) N1 0.0336(7) 0.0421(9) 0.0307(8) -0.0075(7) -0.0052(6) -0.0042(6) N2 0.0233(7) 0.0391(8) 0.0322(8) -0.0022(6) -0.0021(6) -0.0072(6) O1 0.0235(6) 0.0666(10) 0.0783(10) -0.0054(8) 0.0044(6) -0.0065(6) O2 0.0321(6) 0.0493(8) 0.0424(7) -0.0093(6) 0.0096(5) -0.0120(5) O3 0.0814(12) 0.0622(10) 0.0709(11) -0.0337(9) -0.0137(8) 0.0045(8) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 115.45(15) . . ? O1 C1 C9 124.62(17) . . ? O2 C1 C9 119.92(14) . . ? O2 C2 C3 115.93(14) . . ? O2 C2 C7 121.58(15) . . ? C3 C2 C7 122.49(16) . . ? C4 C3 C2 119.05(16) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 120.11(17) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.34(17) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.16(16) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 116.78(15) . . ? C2 C7 C8 118.27(14) . . ? C6 C7 C8 124.93(14) . . ? N2 C8 C9 125.68(15) . . ? N2 C8 C7 116.00(13) . . ? C9 C8 C7 118.32(14) . . ? C8 C9 C1 120.64(15) . . ? C8 C9 C10 124.94(14) . . ? C1 C9 C10 114.42(14) . . ? N1 C10 C9 112.66(14) . . ? N1 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? N1 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C16 C11 C12 119.32(15) . . ? C16 C11 N2 123.49(14) . . ? C12 C11 N2 117.05(14) . . ? C13 C12 C11 120.62(17) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.24(17) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.80(17) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.84(17) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 119.18(15) . . ? C11 C16 N1 120.23(14) . . ? C15 C16 N1 120.56(15) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 C10 114.09(14) . . ? C16 N1 H1N 109.4(12) . . ? C10 N1 H1N 108.5(12) . . ? C8 N2 C11 131.71(13) . . ? C8 N2 H2N 116.2(12) . . ? C11 N2 H2N 111.9(12) . . ? C1 O2 C2 120.83(12) . . ? C17 O3 H3O 108.1(17) . . ? 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 C1 O1 1.2203(19) . ? C1 O2 1.363(2) . ? C1 C9 1.427(2) . ? C2 O2 1.373(2) . ? C2 C3 1.385(2) . ? C2 C7 1.394(2) . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C5 C6 1.375(2) . ? C5 H5 0.9300 . ? C6 C7 1.400(2) . ? C6 H6 0.9300 . ? C7 C8 1.464(2) . ? C8 N2 1.3636(19) . ? C8 C9 1.375(2) . ? C9 C10 1.498(2) . ? C10 N1 1.472(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.391(2) . ? C11 C12 1.394(2) . ? C11 N2 1.415(2) . ? C12 C13 1.372(2) . ? C12 H12 0.9300 . ? C13 C14 1.378(3) . ? C13 H13 0.9300 . ? C14 C15 1.376(3) . ? C14 H14 0.9300 . ? C15 C16 1.392(2) . ? C15 H15 0.9300 . ? C16 N1 1.412(2) . ? C17 O3 1.384(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N1 H1N 0.89(2) . ? N2 H2N 0.902(19) . ? O3 H3O 1.01(3) . ? 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 O2 C2 C3 C4 -177.14(17) . . . . ? C7 C2 C3 C4 2.8(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? O2 C2 C7 C6 177.01(16) . . . . ? C3 C2 C7 C6 -3.0(3) . . . . ? O2 C2 C7 C8 -1.5(2) . . . . ? C3 C2 C7 C8 178.55(16) . . . . ? C5 C6 C7 C2 1.1(3) . . . . ? C5 C6 C7 C8 179.46(17) . . . . ? C2 C7 C8 N2 -173.61(15) . . . . ? C6 C7 C8 N2 8.1(2) . . . . ? C2 C7 C8 C9 6.6(2) . . . . ? C6 C7 C8 C9 -171.70(17) . . . . ? N2 C8 C9 C1 172.86(16) . . . . ? C7 C8 C9 C1 -7.4(3) . . . . ? N2 C8 C9 C10 -7.0(3) . . . . ? C7 C8 C9 C10 172.76(16) . . . . ? O1 C1 C9 C8 -175.91(18) . . . . ? O2 C1 C9 C8 3.0(3) . . . . ? O1 C1 C9 C10 3.9(3) . . . . ? O2 C1 C9 C10 -177.12(16) . . . . ? C8 C9 C10 N1 -35.1(2) . . . . ? C1 C9 C10 N1 145.07(16) . . . . ? C16 C11 C12 C13 0.9(3) . . . . ? N2 C11 C12 C13 -175.07(16) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C12 C11 C16 C15 -0.4(2) . . . . ? N2 C11 C16 C15 175.26(16) . . . . ? C12 C11 C16 N1 -178.20(15) . . . . ? N2 C11 C16 N1 -2.5(2) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? C14 C15 C16 N1 177.64(17) . . . . ? C11 C16 N1 C10 -61.3(2) . . . . ? C15 C16 N1 C10 120.92(17) . . . . ? C9 C10 N1 C16 81.88(18) . . . . ? C9 C8 N2 C11 -3.9(3) . . . . ? C7 C8 N2 C11 176.36(16) . . . . ? C16 C11 N2 C8 31.9(3) . . . . ? C12 C11 N2 C8 -152.39(17) . . . . ? O1 C1 O2 C2 -178.57(16) . . . . ? C9 C1 O2 C2 2.4(3) . . . . ? C3 C2 O2 C1 176.92(16) . . . . ? C7 C2 O2 C1 -3.1(2) . . . . ?