#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:22 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306472 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064382.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_7064382 loop_ _publ_author_name 'Gou, Yan' 'Wang, Jing' 'Li, Na' 'Hou, Shanling' 'Cheng, Yang' 'Li, Yuming' _publ_section_title ; DBU-mediated [3+2] annulation of 3-hydroxyisoindolinones with vinylsulfonium salts: an efficient approach to functionalized oxazolo[2,3-a]isoindolones ; _journal_issue 18 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7609 _journal_page_last 7613 _journal_paper_doi 10.1039/D6NJ00608F _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C18 H17 N O4' _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.32 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2025-01-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2025-01-15 deposited with the CCDC. 2026-04-07 downloaded from the CCDC. ; _cell_angle_alpha 112.254(4) _cell_angle_beta 110.239(4) _cell_angle_gamma 97.809(4) _cell_formula_units_Z 2 _cell_length_a 8.4269(8) _cell_length_b 10.2708(11) _cell_length_c 10.7625(12) _cell_measurement_reflns_used 3529 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.9350 _cell_measurement_theta_min 3.1630 _cell_volume 769.74(15) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293.0 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0474 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7305 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.518 _diffrn_reflns_theta_min 2.269 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.343 _exptl_crystal_description block _exptl_crystal_F_000 328 _refine_diff_density_max 0.228 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.751 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3503 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.751 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0487 _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^)+(0.1090P)^2^+0.4167P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1353 _refine_ls_wR_factor_ref 0.1604 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2516 _reflns_number_total 3503 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00608f2.cif _cod_data_source_block 20250115 _cod_depositor_comments 'Adding full bibliography for 7064382--7064383.cif.' _cod_original_cell_volume 769.74(14) _cod_database_code 7064382 _shelx_shelxl_version_number 2014/7 _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 At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C16(H16), C12(H12), C13(H13), C5(H5), C2(H2), C4(H4), C3(H3) 2.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C17(H17A,H17B,H17C) ; _shelx_res_file ; 20250115.res created by SHELXL-2014/7 TITL 20250115_a.res in P-1 REM Old TITL 20250115 in P-1 REM SHELXT solution in P-1 REM R1 0.215, Rweak 0.013, Alpha 0.066, Orientation as input REM Formula found by SHELXT: C18 O3 O0AA CELL 0.71073 8.4269 10.2708 10.7625 112.254 110.239 97.809 ZERR 2 0.0008 0.0011 0.0012 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 36 34 2 8 L.S. 4 0 0 PLAN 20 TEMP 19.85 list 4 fmap 2 53 acta REM REM REM WGHT 0.109000 0.416700 FVAR 1.96641 O0AA 4 0.879808 1.006565 0.641209 11.00000 0.04190 0.04077 = 0.04547 0.01973 0.01596 0.00816 O3 4 0.511351 0.790536 0.078743 11.00000 0.05695 0.06248 = 0.04252 0.03377 0.00455 -0.00152 O2 4 0.275154 0.554052 -0.000081 11.00000 0.06297 0.05308 = 0.04589 0.02579 -0.00515 -0.00651 O1 4 0.899722 0.809470 0.913675 11.00000 0.09719 0.09788 = 0.04807 0.04715 0.02485 0.00442 N1 3 0.768775 0.840158 0.704180 11.00000 0.04569 0.05620 = 0.03803 0.02293 0.01944 0.00708 C11 1 0.665114 0.772778 0.435570 11.00000 0.03338 0.04218 = 0.03519 0.02053 0.01312 0.01301 C16 1 0.660416 0.824933 0.332654 11.00000 0.03575 0.04148 = 0.03940 0.02190 0.01183 0.00723 AFIX 43 H16 2 0.746433 0.910900 0.361377 11.00000 -1.20000 AFIX 0 C12 1 0.538134 0.644699 0.391845 11.00000 0.04207 0.04781 = 0.04337 0.02819 0.01523 0.00939 AFIX 43 H12 2 0.540939 0.609314 0.460104 11.00000 -1.20000 AFIX 0 C15 1 0.528505 0.749611 0.187860 11.00000 0.04031 0.04343 = 0.03812 0.02405 0.01245 0.01087 C6 1 0.969704 0.784986 0.604344 11.00000 0.03604 0.04116 = 0.03799 0.01868 0.00946 0.00841 C7 1 0.818668 0.850840 0.590493 11.00000 0.03626 0.04245 = 0.03409 0.02147 0.01427 0.00793 C14 1 0.399224 0.619461 0.144484 11.00000 0.03830 0.04136 = 0.03844 0.01860 0.00685 0.00810 C18 1 0.645805 0.913375 0.110967 11.00000 0.05753 0.05806 = 0.05329 0.03652 0.02343 0.01263 AFIX 137 H18A 2 0.623618 0.924545 0.022423 11.00000 -1.50000 H18B 2 0.759387 0.897710 0.145696 11.00000 -1.50000 H18C 2 0.645587 1.001172 0.186634 11.00000 -1.50000 AFIX 0 C13 1 0.405405 0.567674 0.246026 11.00000 0.04155 0.04208 = 0.04973 0.02446 0.01112 0.00279 AFIX 43 H13 2 0.320746 0.480927 0.217388 11.00000 -1.20000 AFIX 0 C5 1 1.060875 0.754582 0.517843 11.00000 0.04502 0.05916 = 0.04766 0.01796 0.01822 0.01543 AFIX 43 H5 2 1.034282 0.775195 0.437250 11.00000 -1.20000 AFIX 0 C1 1 1.008359 0.753925 0.723734 11.00000 0.04695 0.04296 = 0.04484 0.02439 0.00506 0.00463 C10 1 0.892415 0.801941 0.796364 11.00000 0.05818 0.05313 = 0.04132 0.02713 0.01394 -0.00231 C2 1 1.142009 0.691891 0.762439 11.00000 0.06687 0.05456 = 0.07108 0.03597 0.00115 0.01698 AFIX 43 H2 2 1.168731 0.671832 0.843383 11.00000 -1.20000 AFIX 0 C17 1 0.159789 0.411951 -0.058609 11.00000 0.07128 0.04808 = 0.04952 0.01140 0.00530 -0.00341 AFIX 137 H17A 2 0.087252 0.376188 -0.162971 11.00000 -1.50000 H17B 2 0.085200 0.415707 -0.007950 11.00000 -1.50000 H17C 2 0.227935 0.346677 -0.044975 11.00000 -1.50000 AFIX 0 C8 1 0.769651 1.068196 0.707769 11.00000 0.06270 0.05547 = 0.06855 0.02079 0.03290 0.02401 AFIX 23 H8A 2 0.669656 1.076482 0.635280 11.00000 -1.20000 H8B 2 0.837109 1.165868 0.790546 11.00000 -1.20000 AFIX 0 C9 1 0.704891 0.964618 0.761833 11.00000 0.05645 0.07086 = 0.05625 0.01793 0.03228 0.01656 AFIX 23 H9A 2 0.755393 1.010901 0.869749 11.00000 -1.20000 H9B 2 0.576277 0.933719 0.721803 11.00000 -1.20000 AFIX 0 C4 1 1.194526 0.691676 0.556241 11.00000 0.05387 0.07379 = 0.07960 0.01357 0.02371 0.02781 AFIX 43 H4 2 1.258913 0.669666 0.500257 11.00000 -1.20000 AFIX 0 C3 1 1.233451 0.661198 0.676587 11.00000 0.06262 0.06358 = 0.09961 0.02760 0.00570 0.03467 AFIX 43 H3 2 1.323477 0.619042 0.699623 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20250115_a.res in P-1 REM R1 = 0.0487 for 2516 Fo > 4sig(Fo) and 0.0714 for all 3503 data REM 210 parameters refined using 0 restraints END WGHT 0.0608 0.1080 REM Highest difference peak 0.228, deepest hole -0.160, 1-sigma level 0.033 Q1 1 0.7340 0.8254 0.5136 11.00000 0.05 0.23 Q2 1 0.8977 0.8064 0.5782 11.00000 0.05 0.19 Q3 1 0.5927 0.7769 0.2609 11.00000 0.05 0.19 Q4 1 0.9223 0.7262 0.7373 11.00000 0.05 0.18 Q5 1 0.9781 0.7325 0.5458 11.00000 0.05 0.16 Q6 1 0.6886 0.7815 0.3744 11.00000 0.05 0.16 Q7 1 0.4648 0.6219 0.3216 11.00000 0.05 0.15 Q8 1 0.4024 0.7638 0.0018 11.00000 0.05 0.14 Q9 1 0.3624 0.5624 0.0611 11.00000 0.05 0.14 Q10 1 1.0138 0.8032 0.6828 11.00000 0.05 0.13 Q11 1 0.4259 0.7233 0.1925 11.00000 0.05 0.13 Q12 1 0.4770 0.6723 0.1653 11.00000 0.05 0.13 Q13 1 0.7884 0.7942 0.8558 11.00000 0.05 0.13 Q14 1 0.8178 0.8033 0.7361 11.00000 0.05 0.13 Q15 1 0.9794 0.7647 0.6580 11.00000 0.05 0.13 Q16 1 1.1605 0.6210 0.5845 11.00000 0.05 0.13 Q17 1 0.6193 0.7023 0.4028 11.00000 0.05 0.13 Q18 1 0.7275 0.7598 0.6965 11.00000 0.05 0.12 Q19 1 0.2482 0.6207 -0.0439 11.00000 0.05 0.12 Q20 1 1.0635 0.7130 0.7204 11.00000 0.05 0.11 ; _shelx_res_checksum 14038 _olex2_submission_special_instructions 'No special instructions were received' 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 O0AA O 0.87981(15) 1.00656(13) 0.64121(13) 0.0442(3) Uani 1 1 d . . . . . O3 O 0.51135(18) 0.79054(16) 0.07874(14) 0.0582(4) Uani 1 1 d . . . . . O2 O 0.27515(19) 0.55405(16) -0.00008(15) 0.0646(4) Uani 1 1 d . . . . . O1 O 0.8997(2) 0.8095(2) 0.91368(17) 0.0813(5) Uani 1 1 d . . . . . N1 N 0.76877(19) 0.84016(18) 0.70418(16) 0.0468(4) Uani 1 1 d . . . . . C11 C 0.6651(2) 0.77278(18) 0.43557(17) 0.0363(3) Uani 1 1 d . . . . . C16 C 0.6604(2) 0.82493(19) 0.33265(18) 0.0396(4) Uani 1 1 d . . . . . H16 H 0.7464 0.9109 0.3614 0.048 Uiso 1 1 calc R . . . . C12 C 0.5381(2) 0.6447(2) 0.39184(19) 0.0434(4) Uani 1 1 d . . . . . H12 H 0.5409 0.6093 0.4601 0.052 Uiso 1 1 calc R . . . . C15 C 0.5285(2) 0.74961(19) 0.18786(18) 0.0404(4) Uani 1 1 d . . . . . C6 C 0.9697(2) 0.78499(19) 0.60434(18) 0.0406(4) Uani 1 1 d . . . . . C7 C 0.8187(2) 0.85084(18) 0.59049(17) 0.0370(4) Uani 1 1 d . . . . . C14 C 0.3992(2) 0.61946(19) 0.14448(19) 0.0428(4) Uani 1 1 d . . . . . C18 C 0.6458(3) 0.9134(2) 0.1110(2) 0.0533(5) Uani 1 1 d . . . . . H18A H 0.6236 0.9245 0.0224 0.080 Uiso 1 1 calc GR . . . . H18B H 0.7594 0.8977 0.1457 0.080 Uiso 1 1 calc GR . . . . H18C H 0.6456 1.0012 0.1866 0.080 Uiso 1 1 calc GR . . . . C13 C 0.4054(2) 0.5677(2) 0.2460(2) 0.0471(4) Uani 1 1 d . . . . . H13 H 0.3207 0.4809 0.2174 0.057 Uiso 1 1 calc R . . . . C5 C 1.0609(2) 0.7546(2) 0.5178(2) 0.0535(5) Uani 1 1 d . . . . . H5 H 1.0343 0.7752 0.4372 0.064 Uiso 1 1 calc R . . . . C1 C 1.0084(2) 0.7539(2) 0.7237(2) 0.0491(4) Uani 1 1 d . . . . . C10 C 0.8924(3) 0.8019(2) 0.7964(2) 0.0536(5) Uani 1 1 d . . . . . C2 C 1.1420(3) 0.6919(2) 0.7624(3) 0.0708(7) Uani 1 1 d . . . . . H2 H 1.1687 0.6718 0.8434 0.085 Uiso 1 1 calc R . . . . C17 C 0.1598(3) 0.4120(2) -0.0586(2) 0.0690(6) Uani 1 1 d . . . . . H17A H 0.0873 0.3762 -0.1630 0.104 Uiso 1 1 calc GR . . . . H17B H 0.0852 0.4157 -0.0079 0.104 Uiso 1 1 calc GR . . . . H17C H 0.2279 0.3467 -0.0450 0.104 Uiso 1 1 calc GR . . . . C8 C 0.7697(3) 1.0682(2) 0.7078(3) 0.0628(6) Uani 1 1 d . . . . . H8A H 0.6697 1.0765 0.6353 0.075 Uiso 1 1 calc R . . . . H8B H 0.8371 1.1659 0.7905 0.075 Uiso 1 1 calc R . . . . C9 C 0.7049(3) 0.9646(3) 0.7618(2) 0.0629(6) Uani 1 1 d . . . . . H9A H 0.7554 1.0109 0.8697 0.076 Uiso 1 1 calc R . . . . H9B H 0.5763 0.9337 0.7218 0.076 Uiso 1 1 calc R . . . . C4 C 1.1945(3) 0.6917(3) 0.5562(3) 0.0772(7) Uani 1 1 d . . . . . H4 H 1.2589 0.6697 0.5003 0.093 Uiso 1 1 calc R . . . . C3 C 1.2335(3) 0.6612(3) 0.6766(3) 0.0860(9) Uani 1 1 d . . . . . H3 H 1.3235 0.6190 0.6996 0.103 Uiso 1 1 calc R . . . . 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 O0AA 0.0419(6) 0.0408(6) 0.0455(7) 0.0197(5) 0.0160(5) 0.0082(5) O3 0.0569(8) 0.0625(9) 0.0425(7) 0.0338(6) 0.0045(6) -0.0015(6) O2 0.0630(8) 0.0531(8) 0.0459(8) 0.0258(6) -0.0052(6) -0.0065(6) O1 0.0972(12) 0.0979(13) 0.0481(9) 0.0472(9) 0.0248(8) 0.0044(10) N1 0.0457(8) 0.0562(9) 0.0380(7) 0.0229(7) 0.0194(6) 0.0071(7) C11 0.0334(7) 0.0422(9) 0.0352(8) 0.0205(7) 0.0131(6) 0.0130(6) C16 0.0358(8) 0.0415(9) 0.0394(8) 0.0219(7) 0.0118(6) 0.0072(7) C12 0.0421(9) 0.0478(10) 0.0434(9) 0.0282(8) 0.0152(7) 0.0094(7) C15 0.0403(8) 0.0434(9) 0.0381(8) 0.0240(7) 0.0124(7) 0.0109(7) C6 0.0360(8) 0.0412(9) 0.0380(8) 0.0187(7) 0.0095(6) 0.0084(7) C7 0.0363(8) 0.0425(9) 0.0341(8) 0.0215(7) 0.0143(6) 0.0079(6) C14 0.0383(8) 0.0414(9) 0.0384(8) 0.0186(7) 0.0068(7) 0.0081(7) C18 0.0575(11) 0.0581(11) 0.0533(11) 0.0365(9) 0.0234(9) 0.0126(9) C13 0.0415(9) 0.0421(9) 0.0497(10) 0.0245(8) 0.0111(7) 0.0028(7) C5 0.0450(10) 0.0592(12) 0.0477(10) 0.0180(9) 0.0182(8) 0.0154(8) C1 0.0470(9) 0.0430(9) 0.0448(10) 0.0244(8) 0.0051(7) 0.0046(7) C10 0.0582(11) 0.0531(11) 0.0413(9) 0.0271(8) 0.0139(8) -0.0023(8) C2 0.0669(13) 0.0546(12) 0.0711(14) 0.0360(11) 0.0012(11) 0.0170(11) C17 0.0713(14) 0.0481(12) 0.0495(12) 0.0114(9) 0.0053(10) -0.0034(10) C8 0.0627(12) 0.0555(12) 0.0685(13) 0.0208(10) 0.0329(11) 0.0240(10) C9 0.0564(12) 0.0709(14) 0.0562(12) 0.0179(10) 0.0323(10) 0.0166(10) C4 0.0539(12) 0.0738(16) 0.0796(16) 0.0136(13) 0.0237(12) 0.0278(12) C3 0.0626(14) 0.0636(15) 0.100(2) 0.0276(14) 0.0057(14) 0.0347(12) 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 C7 O0AA C8 106.04(14) . . ? C15 O3 C18 117.97(14) . . ? C14 O2 C17 118.42(15) . . ? C10 N1 C7 111.44(15) . . ? C10 N1 C9 122.48(16) . . ? C9 N1 C7 108.12(15) . . ? C16 C11 C7 119.48(14) . . ? C12 C11 C16 119.44(15) . . ? C12 C11 C7 120.89(14) . . ? C15 C16 C11 120.43(15) . . ? C11 C12 C13 120.52(15) . . ? O3 C15 C16 125.31(15) . . ? O3 C15 C14 114.98(14) . . ? C16 C15 C14 119.72(15) . . ? C5 C6 C7 129.60(16) . . ? C5 C6 C1 121.60(17) . . ? C1 C6 C7 108.79(15) . . ? O0AA C7 N1 103.37(13) . . ? O0AA C7 C11 111.75(12) . . ? O0AA C7 C6 111.52(13) . . ? N1 C7 C11 112.97(13) . . ? N1 C7 C6 103.00(13) . . ? C6 C7 C11 113.49(13) . . ? O2 C14 C15 115.12(15) . . ? O2 C14 C13 125.23(16) . . ? C13 C14 C15 119.64(15) . . ? C14 C13 C12 120.25(16) . . ? C6 C5 C4 117.1(2) . . ? C6 C1 C10 109.06(16) . . ? C6 C1 C2 121.3(2) . . ? C2 C1 C10 129.6(2) . . ? O1 C10 N1 124.9(2) . . ? O1 C10 C1 128.8(2) . . ? N1 C10 C1 106.32(15) . . ? C3 C2 C1 117.4(2) . . ? O0AA C8 C9 106.97(16) . . ? N1 C9 C8 102.92(15) . . ? C3 C4 C5 121.1(2) . . ? C2 C3 C4 121.5(2) . . ? 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 O0AA C7 1.429(2) . ? O0AA C8 1.432(2) . ? O3 C15 1.360(2) . ? O3 C18 1.416(2) . ? O2 C14 1.363(2) . ? O2 C17 1.402(2) . ? O1 C10 1.214(2) . ? N1 C7 1.460(2) . ? N1 C10 1.384(3) . ? N1 C9 1.458(3) . ? C11 C16 1.393(2) . ? C11 C12 1.377(2) . ? C11 C7 1.520(2) . ? C16 C15 1.385(2) . ? C12 C13 1.394(2) . ? C15 C14 1.404(2) . ? C6 C7 1.510(2) . ? C6 C5 1.376(3) . ? C6 C1 1.381(2) . ? C14 C13 1.374(2) . ? C5 C4 1.391(3) . ? C1 C10 1.475(3) . ? C1 C2 1.385(3) . ? C2 C3 1.373(4) . ? C8 C9 1.516(3) . ? C4 C3 1.387(4) . ?