#------------------------------------------------------------------------------ #$Date: 2020-04-24 04:33:46 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251123 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240389.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_7240389 loop_ _publ_author_name 'Lee, Jaegyeong' 'Yoon, Minyoung' 'Lee, Hyosun' 'Nayab, Saira' _publ_section_title ; Stereoselective polymerization of methyl methacrylate and rac-lactide mediated by iminomethylpyridine based Cu(ii) complexes ; _journal_issue 27 _journal_name_full 'RSC Advances' _journal_page_first 16209 _journal_paper_doi 10.1039/D0RA00805B _journal_volume 10 _journal_year 2020 _chemical_formula_sum 'C13 H19 Cl2 Cu N3' _chemical_formula_weight 351.75 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-26 deposited with the CCDC. 2020-04-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.988(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3629(19) _cell_length_b 6.8532(11) _cell_length_c 19.328(3) _cell_measurement_reflns_used 2720 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 26.53 _cell_measurement_theta_min 3.17 _cell_volume 1453.9(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Mercury 4.1.0' _computing_publication_material 'enCIFer 1.7.1' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2017)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_unetI/netI 0.0925 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 10315 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.354 _diffrn_reflns_theta_min 2.182 _exptl_absorpt_coefficient_mu 1.859 _exptl_absorpt_correction_T_max 0.8359 _exptl_absorpt_correction_T_min 0.6241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.607 _exptl_crystal_description block _exptl_crystal_F_000 724 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.853 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.155 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 3595 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0431 _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^)+(0.0408P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0830 _refine_ls_wR_factor_ref 0.1178 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2084 _reflns_number_total 3595 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra00805b2.cif _cod_data_source_block SL6Cu-a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240389 _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 0.624 _shelx_estimated_absorpt_t_max 0.836 _shelx_res_file ; TITL SL6Cu in P2(1)/n SL6Cu-a.res created by SHELXL-2018/3 at 18:05:41 on 24-Mar-2020 CELL 0.71073 11.3629 6.8532 19.3277 90.000 104.988 90.000 ZERR 4.00 0.0019 0.0011 0.0033 0.000 0.004 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N Cl Cu UNIT 52 76 12 8 4 ACTA LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 32 OMIT -13 0 11 OMIT -3 8 2 OMIT 9 5 6 OMIT 8 6 7 OMIT -14 1 10 OMIT 10 5 3 OMIT -13 0 13 OMIT 2 0 22 OMIT -13 0 5 OMIT -13 0 9 OMIT -2 1 23 OMIT 0 1 24 OMIT 9 5 4 OMIT 6 5 10 OMIT 9 5 8 OMIT 9 6 4 OMIT 7 5 9 OMIT 8 6 5 OMIT -6 6 15 OMIT -3 0 23 BOND FMAP 2 PLAN 20 SIZE 0.28 0.14 0.10 TEMP -73 WGHT 0.040800 FVAR 0.46859 MOLE 1 CU1 5 0.545928 0.723960 0.199783 11.00000 0.02527 0.02110 = 0.02334 -0.00095 0.00999 -0.00325 CL1 4 0.349830 0.885625 0.122892 11.00000 0.03162 0.03092 = 0.02812 -0.00112 0.00493 0.00369 CL2 4 0.667802 0.980613 0.237198 11.00000 0.02666 0.02386 = 0.03172 -0.00247 0.00913 -0.00571 N1 3 0.483911 0.689728 0.291838 11.00000 0.01962 0.01961 = 0.02008 -0.00038 0.00478 0.00009 N2 3 0.500002 0.446564 0.187158 11.00000 0.02712 0.01996 = 0.02422 0.00152 0.00847 0.00001 C1 1 0.430335 0.872079 0.311700 11.00000 0.02601 0.02652 = 0.03226 0.00311 0.01252 0.00480 AFIX 23 H1A 2 0.358813 0.908150 0.272360 11.00000 -1.20000 H1AB 2 0.491019 0.978262 0.316634 11.00000 -1.20000 AFIX 0 C2 1 0.390737 0.857020 0.381018 11.00000 0.02996 0.03449 = 0.03492 -0.00135 0.01424 0.00481 AFIX 23 H2A 2 0.324261 0.760128 0.375165 11.00000 -1.20000 H2AB 2 0.359312 0.984842 0.392083 11.00000 -1.20000 AFIX 0 C3 1 0.497755 0.795623 0.442576 11.00000 0.04086 0.03832 = 0.02846 0.00097 0.01361 0.00064 AFIX 23 H3A 2 0.469186 0.774094 0.486213 11.00000 -1.20000 H3AB 2 0.559470 0.900946 0.452753 11.00000 -1.20000 AFIX 0 C4 1 0.555210 0.608666 0.423577 11.00000 0.03554 0.03548 = 0.02503 0.00594 0.00498 0.00554 AFIX 23 H4A 2 0.497210 0.499150 0.420309 11.00000 -1.20000 H4AB 2 0.629322 0.577899 0.461923 11.00000 -1.20000 AFIX 0 C5 1 0.588956 0.630279 0.351975 11.00000 0.02503 0.02822 = 0.02373 -0.00124 0.00783 0.00160 AFIX 23 H5A 2 0.654411 0.728868 0.357472 11.00000 -1.20000 H5AB 2 0.621359 0.504379 0.339808 11.00000 -1.20000 AFIX 0 C6 1 0.389001 0.533089 0.271216 11.00000 0.02667 0.03303 = 0.02634 0.00031 0.01169 -0.00603 AFIX 23 H6A 2 0.316131 0.585761 0.236424 11.00000 -1.20000 H6AB 2 0.364259 0.488823 0.314143 11.00000 -1.20000 AFIX 0 C7 1 0.439337 0.362943 0.238316 11.00000 0.03958 0.02010 = 0.02983 0.00198 0.01085 -0.01105 AFIX 23 H7A 2 0.498025 0.288090 0.275672 11.00000 -1.20000 H7AB 2 0.372781 0.274471 0.213675 11.00000 -1.20000 AFIX 0 C8 1 0.531487 0.350420 0.138960 11.00000 0.02990 0.02039 = 0.02330 0.00139 -0.00004 0.00044 AFIX 43 H8 2 0.514370 0.215226 0.131509 11.00000 -1.20000 AFIX 0 C9 1 0.596388 0.462103 0.095236 11.00000 0.02422 0.02645 = 0.01702 -0.00154 0.00062 0.00453 C10 1 0.634219 0.385275 0.038625 11.00000 0.02267 0.02740 = 0.02271 -0.00455 -0.00167 0.00473 AFIX 43 H10 2 0.623744 0.250461 0.027259 11.00000 -1.20000 AFIX 0 C11 1 0.687845 0.508286 -0.001446 11.00000 0.02716 0.04208 = 0.02021 -0.00500 0.00628 0.00192 AFIX 43 H11 2 0.714533 0.458747 -0.040720 11.00000 -1.20000 AFIX 0 C12 1 0.701904 0.702721 0.016359 11.00000 0.03012 0.03995 = 0.02843 -0.00103 0.01156 -0.00562 AFIX 43 H12 2 0.737456 0.789839 -0.010702 11.00000 -1.20000 AFIX 0 C13 1 0.663002 0.769501 0.074854 11.00000 0.02765 0.03044 = 0.02556 0.00161 0.00377 -0.00378 AFIX 43 H13 2 0.673125 0.903750 0.087207 11.00000 -1.20000 AFIX 0 N3 3 0.612335 0.653337 0.114098 11.00000 0.02211 0.02010 = 0.02523 -0.00185 0.00457 -0.00183 HKLF 4 REM SL6Cu in P2(1)/n REM wR2 = 0.1178, GooF = S = 1.029, Restrained GooF = 1.029 for all data REM R1 = 0.0431 for 2084 Fo > 4sig(Fo) and 0.1051 for all 3595 data REM 172 parameters refined using 0 restraints END WGHT 0.0408 0.0000 REM Highest difference peak 0.853, deepest hole -1.014, 1-sigma level 0.155 Q1 1 0.2417 0.9842 0.3643 11.00000 0.05 0.85 Q2 1 0.3658 0.7237 0.4022 11.00000 0.05 0.77 Q3 1 0.5432 0.8170 0.2035 11.00000 0.05 0.75 Q4 1 0.6436 0.6526 0.1829 11.00000 0.05 0.73 Q5 1 0.4250 0.9846 0.1607 11.00000 0.05 0.72 Q6 1 0.4557 0.8516 0.1718 11.00000 0.05 0.70 Q7 1 0.3615 0.6729 0.1285 11.00000 0.05 0.67 Q8 1 0.7494 0.8761 0.2726 11.00000 0.05 0.67 Q9 1 0.5758 0.5917 0.1743 11.00000 0.05 0.64 Q10 1 0.5177 0.6073 0.2284 11.00000 0.05 0.63 Q11 1 0.5602 0.6235 0.0953 11.00000 0.05 0.62 Q12 1 0.6625 0.4591 0.2289 11.00000 0.05 0.61 Q13 1 0.5032 0.5398 0.1892 11.00000 0.05 0.60 Q14 1 0.6285 0.8424 0.2306 11.00000 0.05 0.60 Q15 1 0.3287 1.0020 0.1450 11.00000 0.05 0.57 Q16 1 0.5931 0.4731 0.0572 11.00000 0.05 0.56 Q17 1 0.3038 0.9017 0.0970 11.00000 0.05 0.56 Q18 1 0.5650 0.8840 0.4765 11.00000 0.05 0.56 Q19 1 0.5776 0.5212 0.2264 11.00000 0.05 0.55 Q20 1 0.4787 0.8756 0.3036 11.00000 0.05 0.55 ; _shelx_res_checksum 99557 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' '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_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 Cu1 Cu 0.54593(4) 0.72396(7) 0.19978(3) 0.02255(16) Uani 1 1 d . . . . . Cl1 Cl 0.34983(9) 0.88562(16) 0.12289(6) 0.0307(3) Uani 1 1 d . . . . . Cl2 Cl 0.66780(9) 0.98061(15) 0.23720(6) 0.0271(3) Uani 1 1 d . . . . . N1 N 0.4839(3) 0.6897(5) 0.29184(17) 0.0198(7) Uani 1 1 d . . . . . N2 N 0.5000(3) 0.4466(5) 0.18716(18) 0.0234(8) Uani 1 1 d . . . . . C1 C 0.4303(4) 0.8721(6) 0.3117(2) 0.0273(10) Uani 1 1 d . . . . . H1A H 0.358813 0.908150 0.272360 0.033 Uiso 1 1 calc R U . . . H1AB H 0.491019 0.978262 0.316634 0.033 Uiso 1 1 calc R U . . . C2 C 0.3907(4) 0.8570(7) 0.3810(2) 0.0320(11) Uani 1 1 d . . . . . H2A H 0.324261 0.760128 0.375165 0.038 Uiso 1 1 calc R U . . . H2AB H 0.359312 0.984842 0.392083 0.038 Uiso 1 1 calc R U . . . C3 C 0.4978(4) 0.7956(7) 0.4426(2) 0.0350(11) Uani 1 1 d . . . . . H3A H 0.469186 0.774094 0.486213 0.042 Uiso 1 1 calc R U . . . H3AB H 0.559470 0.900946 0.452753 0.042 Uiso 1 1 calc R U . . . C4 C 0.5552(4) 0.6087(6) 0.4236(2) 0.0325(11) Uani 1 1 d . . . . . H4A H 0.497210 0.499150 0.420309 0.039 Uiso 1 1 calc R U . . . H4AB H 0.629322 0.577899 0.461923 0.039 Uiso 1 1 calc R U . . . C5 C 0.5890(4) 0.6303(6) 0.3520(2) 0.0254(9) Uani 1 1 d . . . . . H5A H 0.654411 0.728868 0.357472 0.030 Uiso 1 1 calc R U . . . H5AB H 0.621359 0.504379 0.339808 0.030 Uiso 1 1 calc R U . . . C6 C 0.3890(4) 0.5331(6) 0.2712(2) 0.0278(10) Uani 1 1 d . . . . . H6A H 0.316131 0.585761 0.236424 0.033 Uiso 1 1 calc R U . . . H6AB H 0.364259 0.488823 0.314143 0.033 Uiso 1 1 calc R U . . . C7 C 0.4393(4) 0.3629(6) 0.2383(2) 0.0295(10) Uani 1 1 d . . . . . H7A H 0.498025 0.288090 0.275672 0.035 Uiso 1 1 calc R U . . . H7AB H 0.372781 0.274471 0.213675 0.035 Uiso 1 1 calc R U . . . C8 C 0.5315(4) 0.3504(6) 0.1390(2) 0.0258(10) Uani 1 1 d . . . . . H8 H 0.514370 0.215226 0.131509 0.031 Uiso 1 1 calc R U . . . C9 C 0.5964(4) 0.4621(6) 0.0952(2) 0.0234(9) Uani 1 1 d . . . . . C10 C 0.6342(3) 0.3853(6) 0.0386(2) 0.0257(10) Uani 1 1 d . . . . . H10 H 0.623744 0.250461 0.027259 0.031 Uiso 1 1 calc R U . . . C11 C 0.6878(4) 0.5083(7) -0.0014(2) 0.0298(10) Uani 1 1 d . . . . . H11 H 0.714533 0.458747 -0.040720 0.036 Uiso 1 1 calc R U . . . C12 C 0.7019(4) 0.7027(7) 0.0164(2) 0.0321(11) Uani 1 1 d . . . . . H12 H 0.737456 0.789839 -0.010702 0.039 Uiso 1 1 calc R U . . . C13 C 0.6630(4) 0.7695(6) 0.0749(2) 0.0285(10) Uani 1 1 d . . . . . H13 H 0.673125 0.903750 0.087207 0.034 Uiso 1 1 calc R U . . . N3 N 0.6123(3) 0.6533(5) 0.11410(18) 0.0228(8) Uani 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 Cu1 0.0253(3) 0.0211(3) 0.0233(3) -0.0010(2) 0.0100(2) -0.0033(2) Cl1 0.0316(6) 0.0309(6) 0.0281(6) -0.0011(5) 0.0049(5) 0.0037(5) Cl2 0.0267(5) 0.0239(6) 0.0317(6) -0.0025(5) 0.0091(5) -0.0057(4) N1 0.0196(17) 0.0196(18) 0.0201(18) -0.0004(14) 0.0048(14) 0.0001(14) N2 0.0271(19) 0.0200(19) 0.024(2) 0.0015(15) 0.0085(16) 0.0000(15) C1 0.026(2) 0.027(2) 0.032(3) 0.003(2) 0.013(2) 0.0048(19) C2 0.030(2) 0.034(3) 0.035(3) -0.001(2) 0.014(2) 0.005(2) C3 0.041(3) 0.038(3) 0.028(3) 0.001(2) 0.014(2) 0.001(2) C4 0.036(3) 0.035(3) 0.025(2) 0.006(2) 0.005(2) 0.006(2) C5 0.025(2) 0.028(2) 0.024(2) -0.0012(19) 0.0078(18) 0.0016(19) C6 0.027(2) 0.033(3) 0.026(2) 0.000(2) 0.0117(19) -0.006(2) C7 0.040(3) 0.020(2) 0.030(3) 0.0020(19) 0.011(2) -0.011(2) C8 0.030(2) 0.020(2) 0.023(2) 0.0014(18) 0.0000(19) 0.0004(19) C9 0.024(2) 0.026(2) 0.017(2) -0.0015(18) 0.0006(17) 0.0045(18) C10 0.023(2) 0.027(2) 0.023(2) -0.0046(19) -0.0017(19) 0.0047(19) C11 0.027(2) 0.042(3) 0.020(2) -0.005(2) 0.0063(19) 0.002(2) C12 0.030(2) 0.040(3) 0.028(3) -0.001(2) 0.012(2) -0.006(2) C13 0.028(2) 0.030(3) 0.026(2) 0.002(2) 0.0038(19) -0.004(2) N3 0.0221(18) 0.0201(18) 0.025(2) -0.0018(15) 0.0046(15) -0.0018(15) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 N2 Cu1 N3 79.22(13) . . ? N2 Cu1 N1 81.97(13) . . ? N3 Cu1 N1 159.75(13) . . ? N2 Cu1 Cl2 156.90(10) . . ? N3 Cu1 Cl2 96.91(9) . . ? N1 Cu1 Cl2 97.46(9) . . ? N2 Cu1 Cl1 100.43(10) . . ? N3 Cu1 Cl1 94.56(9) . . ? N1 Cu1 Cl1 96.15(9) . . ? Cl2 Cu1 Cl1 102.59(4) . . ? C1 N1 C5 109.1(3) . . ? C1 N1 C6 110.9(3) . . ? C5 N1 C6 112.8(3) . . ? C1 N1 Cu1 112.2(2) . . ? C5 N1 Cu1 108.4(2) . . ? C6 N1 Cu1 103.4(2) . . ? C8 N2 C7 124.5(3) . . ? C8 N2 Cu1 118.5(3) . . ? C7 N2 Cu1 116.8(3) . . ? N1 C1 C2 113.9(3) . . ? C1 C2 C3 110.4(3) . . ? C2 C3 C4 110.4(4) . . ? C3 C4 C5 111.0(4) . . ? N1 C5 C4 113.1(3) . . ? N1 C6 C7 109.9(3) . . ? N2 C7 C6 106.2(3) . . ? N2 C8 C9 115.5(4) . . ? N3 C9 C10 122.2(4) . . ? N3 C9 C8 113.5(3) . . ? C10 C9 C8 124.2(4) . . ? C9 C10 C11 118.9(4) . . ? C12 C11 C10 119.2(4) . . ? C11 C12 C13 118.7(4) . . ? N3 C13 C12 122.8(4) . . ? C13 N3 C9 118.1(4) . . ? C13 N3 Cu1 128.7(3) . . ? C9 N3 Cu1 113.2(3) . . ? 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 Cu1 N2 1.970(3) . ? Cu1 N3 2.048(3) . ? Cu1 N1 2.089(3) . ? Cu1 Cl2 2.2397(11) . ? Cu1 Cl1 2.5862(12) . ? N1 C1 1.483(5) . ? N1 C5 1.491(5) . ? N1 C6 1.501(5) . ? N2 C8 1.266(5) . ? N2 C7 1.461(5) . ? C1 C2 1.523(6) . ? C2 C3 1.524(6) . ? C3 C4 1.525(6) . ? C4 C5 1.536(5) . ? C6 C7 1.510(6) . ? C8 C9 1.472(6) . ? C9 N3 1.360(5) . ? C9 C10 1.379(5) . ? C10 C11 1.388(6) . ? C11 C12 1.375(6) . ? C12 C13 1.393(6) . ? C13 N3 1.329(5) . ?