#------------------------------------------------------------------------------ #$Date: 2020-05-01 04:34:16 +0300 (Fri, 01 May 2020) $ #$Revision: 251350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240436.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_7240436 loop_ _publ_author_name 'Verpekin, Victor V.' 'Semeikin, Oleg V.' 'Vasiliev, Alexander D.' 'Kondrasenko, Alexander A.' 'Belousov, Yuri A.' 'Ustynyuk, Nikolai A.' _publ_section_title ; Catalyzed M--C coupling reactions in the synthesis of \s-(pyridylethynyl)dicarbonylcyclopentadienyliron complexes ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 17014 _journal_paper_doi 10.1039/D0RA02333G _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H9 Fe N O2' _chemical_formula_sum 'C14 H9 Fe N O2' _chemical_formula_weight 279.07 _chemical_name_systematic dicarbonyl(4-pyridylethynyl)(\h^5^-cyclopentadienyl)iron _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-12-20 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.1838(17) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.9444(13) _cell_length_b 9.1089(7) _cell_length_c 17.4069(14) _cell_measurement_reflns_used 3249 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.11 _cell_measurement_theta_min 2.56 _cell_volume 2450.9(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker PHOTON 2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL (Sheldrick 2015)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker PHOTON-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_unetI/netI 0.0300 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 13414 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.995 _diffrn_reflns_theta_min 2.565 _exptl_absorpt_coefficient_mu 1.221 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.5912 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.513 _exptl_crystal_description plate _exptl_crystal_F_000 1136 _exptl_crystal_recrystallization_method 'Vapour deposition' _exptl_crystal_size_max 0.610 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.414 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2678 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0523 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+3.4496P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1134 _refine_ls_wR_factor_ref 0.1221 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2067 _reflns_number_total 2678 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02333g2.cif _cod_data_source_block V479 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7240436 _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. ; _shelx_estimated_absorpt_t_min 0.523 _shelx_estimated_absorpt_t_max 0.909 _shelx_res_file ; V479.res created by SHELXL-2014/7 TITL V479 in C2/c CELL 0.71073 16.94440 9.10890 17.40690 90.0000 114.1838 90.0000 ZERR 8.00 0.00130 0.00070 0.00140 0.0000 0.0017 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O FE UNIT 112 72 8 16 8 TEMP 23.000 SIZE 0.08 0.32 0.61 L.S. 20 BOND $H acta omit -2 54 LIST 6 FMAP 2 PLAN 40 WGHT 0.043300 3.449600 FVAR 0.09398 FE 5 0.352651 0.513438 0.539499 11.00000 0.09345 0.03940 = 0.06804 0.00331 0.05282 0.00552 C1 1 0.238572 0.503462 0.492207 11.00000 0.09750 0.06335 = 0.07972 0.00949 0.05691 0.01679 O1 4 0.165502 0.496672 0.461937 11.00000 0.09596 0.11393 = 0.10828 0.01046 0.05257 0.01354 C2 1 0.359893 0.648680 0.470373 11.00000 0.11907 0.05068 = 0.07655 0.00005 0.05572 -0.00448 O2 4 0.365723 0.732975 0.425845 11.00000 0.19337 0.07405 = 0.09656 0.01850 0.07972 -0.01621 C3 1 0.454301 0.404043 0.635760 11.00000 0.11877 0.06550 = 0.07761 0.01527 0.05343 0.02094 H3 2 0.480649 0.329883 0.626021 11.00000 0.08934 C4 1 0.379700 0.395905 0.650334 11.00000 0.13229 0.06090 = 0.07730 0.00623 0.06497 -0.01545 H4 2 0.351563 0.327023 0.652360 11.00000 0.07616 C5 1 0.355772 0.540673 0.659974 11.00000 0.11178 0.07822 = 0.07076 0.00165 0.05929 0.00389 H5 2 0.305583 0.567713 0.666049 11.00000 0.07387 C6 1 0.413896 0.636532 0.649173 11.00000 0.11384 0.06037 = 0.06889 -0.00707 0.04732 -0.00592 H6 2 0.417607 0.738895 0.654125 11.00000 0.10379 C7 1 0.475664 0.551384 0.633798 11.00000 0.08925 0.08265 = 0.08457 0.01314 0.04538 -0.00205 H7 2 0.522142 0.575624 0.629582 11.00000 0.06710 C8 1 0.357975 0.366340 0.463905 11.00000 0.08212 0.04545 = 0.07294 0.00130 0.04541 0.00281 C9 1 0.361076 0.274485 0.415547 11.00000 0.07821 0.05029 = 0.07288 0.00102 0.04205 0.00197 C10 1 0.368148 0.164297 0.360810 11.00000 0.07704 0.04238 = 0.06530 -0.00174 0.04462 -0.00379 C11 1 0.443161 0.083785 0.380487 11.00000 0.08843 0.04821 = 0.06833 -0.00079 0.03666 0.00156 H11 2 0.485511 0.092248 0.428423 11.00000 0.08603 C12 1 0.445957 -0.020445 0.323638 11.00000 0.11206 0.05458 = 0.12325 -0.00209 0.07136 0.01533 H12 2 0.492187 -0.057937 0.339967 11.00000 0.09993 C13 1 0.312217 0.024819 0.234194 11.00000 0.11271 0.08728 = 0.07845 -0.02519 0.05044 -0.02941 H13 2 0.267091 0.009251 0.192314 11.00000 0.05239 C14 1 0.301666 0.133374 0.283768 11.00000 0.08205 0.06366 = 0.07869 -0.00159 0.04691 -0.00333 H14 2 0.257721 0.185752 0.268089 11.00000 0.05522 N 3 0.382257 -0.052389 0.252010 11.00000 0.13489 0.06439 = 0.09933 -0.02376 0.07237 -0.01253 HKLF 4 REM V479 in C2/c REM R1 = 0.0523 for 2067 Fo > 4sig(Fo) and 0.0709 for all 2678 data REM 199 parameters refined using 0 restraints END WGHT 0.0385 3.2832 REM Highest difference peak 0.414, deepest hole -0.293, 1-sigma level 0.050 Q1 1 0.4146 0.4992 0.5527 11.00000 0.05 0.41 Q2 1 0.2908 0.5022 0.5386 11.00000 0.05 0.38 Q3 1 0.3313 0.4278 0.5001 11.00000 0.05 0.37 Q4 1 0.3582 0.6132 0.5386 11.00000 0.05 0.26 Q5 1 0.3899 0.0826 0.3796 11.00000 0.05 0.21 Q6 1 0.3946 0.6603 0.4275 11.00000 0.05 0.19 Q7 1 0.3626 0.5610 0.4877 11.00000 0.05 0.19 Q8 1 0.4202 0.1618 0.3668 11.00000 0.05 0.19 Q9 1 0.3277 0.2753 0.4222 11.00000 0.05 0.17 Q10 1 0.3217 0.1414 0.3344 11.00000 0.05 0.17 Q11 1 0.3580 0.2395 0.3731 11.00000 0.05 0.16 Q12 1 0.3554 0.3587 0.4015 11.00000 0.05 0.16 Q13 1 0.2699 0.5723 0.4950 11.00000 0.05 0.16 Q14 1 0.1503 0.5063 0.4918 11.00000 0.05 0.16 Q15 1 0.4314 -0.0958 0.2889 11.00000 0.05 0.15 Q16 1 0.4067 0.2949 0.4395 11.00000 0.05 0.15 Q17 1 0.3354 0.5767 0.5897 11.00000 0.05 0.15 Q18 1 0.4099 0.3699 0.6275 11.00000 0.05 0.15 Q19 1 0.3911 0.2763 0.6707 11.00000 0.05 0.14 Q20 1 0.3869 0.2773 0.4706 11.00000 0.05 0.14 Q21 1 0.3362 0.6283 0.4269 11.00000 0.05 0.13 Q22 1 0.3280 0.8078 0.5800 11.00000 0.05 0.13 Q23 1 0.3246 0.7346 0.4309 11.00000 0.05 0.13 Q24 1 0.3334 -0.0929 0.2219 11.00000 0.05 0.13 Q25 1 0.4860 0.0418 0.4762 11.00000 0.05 0.12 Q26 1 0.3782 0.7537 0.6271 11.00000 0.05 0.12 Q27 1 0.6038 0.4960 0.6434 11.00000 0.05 0.12 Q28 1 0.1130 0.5336 0.4861 11.00000 0.05 0.12 Q29 1 0.3815 0.2994 0.5733 11.00000 0.05 0.12 Q30 1 0.1778 0.4280 0.4598 11.00000 0.05 0.12 Q31 1 0.4048 -0.2136 0.2900 11.00000 0.05 0.12 Q32 1 0.1796 0.5852 0.4559 11.00000 0.05 0.12 Q33 1 0.3454 0.4364 0.3904 11.00000 0.05 0.12 Q34 1 0.2291 0.2369 0.2615 11.00000 0.05 0.12 Q35 1 0.2137 0.5103 0.5179 11.00000 0.05 0.12 Q36 1 0.3579 0.1546 0.3217 11.00000 0.05 0.12 Q37 1 0.5213 0.1415 0.4615 11.00000 0.05 0.11 Q38 1 0.3127 0.7838 0.5076 11.00000 0.05 0.11 Q39 1 0.3568 0.4671 0.6382 11.00000 0.05 0.11 Q40 1 0.3086 0.2879 0.6281 11.00000 0.05 0.11 ; _shelx_res_checksum 99700 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 Fe Fe 0.35265(4) 0.51344(4) 0.53950(3) 0.0605(2) Uani 1 1 d . . . . . C1 C 0.2386(3) 0.5035(4) 0.4922(3) 0.0734(11) Uani 1 1 d . . . . . O1 O 0.1655(2) 0.4967(4) 0.4619(2) 0.1025(10) Uani 1 1 d . . . . . C2 C 0.3599(3) 0.6487(4) 0.4704(3) 0.0770(11) Uani 1 1 d . . . . . O2 O 0.3657(3) 0.7330(3) 0.4258(2) 0.1147(12) Uani 1 1 d . . . . . C3 C 0.4543(3) 0.4040(5) 0.6358(3) 0.0830(13) Uani 1 1 d . . . . . H3 H 0.481(3) 0.330(5) 0.626(3) 0.089(14) Uiso 1 1 d . . . . . C4 C 0.3797(4) 0.3959(5) 0.6503(3) 0.0829(13) Uani 1 1 d . . . . . H4 H 0.352(2) 0.327(4) 0.652(2) 0.076(12) Uiso 1 1 d . . . . . C5 C 0.3558(3) 0.5407(5) 0.6600(3) 0.0797(12) Uani 1 1 d . . . . . H5 H 0.306(2) 0.568(4) 0.666(2) 0.074(11) Uiso 1 1 d . . . . . C6 C 0.4139(3) 0.6365(5) 0.6492(3) 0.0778(11) Uani 1 1 d . . . . . H6 H 0.418(3) 0.739(5) 0.654(3) 0.104(15) Uiso 1 1 d . . . . . C7 C 0.4757(3) 0.5514(5) 0.6338(3) 0.0823(12) Uani 1 1 d . . . . . H7 H 0.522(2) 0.576(4) 0.630(2) 0.067(11) Uiso 1 1 d . . . . . C8 C 0.3580(2) 0.3663(3) 0.4639(2) 0.0624(9) Uani 1 1 d . . . . . C9 C 0.3611(2) 0.2745(4) 0.4155(2) 0.0635(9) Uani 1 1 d . . . . . C10 C 0.3681(2) 0.1643(3) 0.3608(2) 0.0565(8) Uani 1 1 d . . . . . C11 C 0.4432(3) 0.0838(4) 0.3805(3) 0.0668(10) Uani 1 1 d . . . . . H11 H 0.486(2) 0.092(4) 0.428(2) 0.086(14) Uiso 1 1 d . . . . . C12 C 0.4460(4) -0.0204(5) 0.3236(4) 0.0890(15) Uani 1 1 d . . . . . H12 H 0.492(3) -0.058(5) 0.340(3) 0.100(18) Uiso 1 1 d . . . . . C13 C 0.3122(4) 0.0248(6) 0.2342(3) 0.0891(14) Uani 1 1 d . . . . . H13 H 0.267(2) 0.009(4) 0.192(2) 0.052(10) Uiso 1 1 d . . . . . C14 C 0.3017(3) 0.1334(4) 0.2838(3) 0.0702(10) Uani 1 1 d . . . . . H14 H 0.258(2) 0.186(4) 0.268(2) 0.055(11) Uiso 1 1 d . . . . . N N 0.3823(3) -0.0524(4) 0.2520(3) 0.0915(12) 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 Fe 0.0935(4) 0.0394(3) 0.0680(3) 0.0033(2) 0.0528(3) 0.0055(2) C1 0.097(3) 0.063(2) 0.080(3) 0.0095(19) 0.057(2) 0.017(2) O1 0.096(2) 0.114(3) 0.108(3) 0.0105(19) 0.053(2) 0.014(2) C2 0.119(3) 0.0507(19) 0.077(3) 0.0000(17) 0.056(3) -0.004(2) O2 0.193(4) 0.0740(19) 0.097(2) 0.0185(16) 0.080(3) -0.016(2) C3 0.119(4) 0.065(2) 0.078(3) 0.015(2) 0.053(3) 0.021(2) C4 0.132(4) 0.061(2) 0.077(3) 0.0062(19) 0.065(3) -0.015(3) C5 0.112(4) 0.078(3) 0.071(3) 0.0017(19) 0.059(3) 0.004(2) C6 0.114(3) 0.060(2) 0.069(2) -0.0071(18) 0.047(2) -0.006(2) C7 0.089(3) 0.083(3) 0.085(3) 0.013(2) 0.045(3) -0.002(2) C8 0.082(2) 0.0455(16) 0.073(2) 0.0013(15) 0.045(2) 0.0028(16) C9 0.078(2) 0.0503(18) 0.073(2) 0.0010(16) 0.042(2) 0.0020(16) C10 0.077(2) 0.0424(15) 0.065(2) -0.0017(14) 0.0446(19) -0.0038(15) C11 0.088(3) 0.0482(18) 0.068(3) -0.0008(16) 0.037(2) 0.0016(19) C12 0.112(4) 0.055(2) 0.123(4) -0.002(2) 0.071(4) 0.015(3) C13 0.113(4) 0.087(3) 0.078(3) -0.025(2) 0.050(3) -0.029(3) C14 0.082(3) 0.064(2) 0.079(3) -0.0016(19) 0.047(2) -0.003(2) N 0.135(4) 0.064(2) 0.099(3) -0.0238(19) 0.072(3) -0.013(2) 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' Fe Fe 0.3463 0.8444 '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 C2 Fe C1 94.98(19) . . ? C2 Fe C8 89.07(16) . . ? C1 Fe C8 89.68(17) . . ? C2 Fe C4 160.1(2) . . ? C1 Fe C4 100.86(19) . . ? C8 Fe C4 102.89(16) . . ? C2 Fe C6 95.82(17) . . ? C1 Fe C6 119.55(18) . . ? C8 Fe C6 149.64(18) . . ? C4 Fe C6 65.88(18) . . ? C2 Fe C7 95.44(19) . . ? C1 Fe C7 157.67(18) . . ? C8 Fe C7 110.18(18) . . ? C4 Fe C7 65.63(19) . . ? C6 Fe C7 39.59(17) . . ? C2 Fe C5 128.47(17) . . ? C1 Fe C5 92.68(19) . . ? C8 Fe C5 141.91(16) . . ? C4 Fe C5 39.44(16) . . ? C6 Fe C5 38.73(16) . . ? C7 Fe C5 65.46(19) . . ? C2 Fe C3 127.9(2) . . ? C1 Fe C3 137.01(18) . . ? C8 Fe C3 87.82(17) . . ? C4 Fe C3 38.78(17) . . ? C6 Fe C3 65.59(18) . . ? C7 Fe C3 38.91(18) . . ? C5 Fe C3 65.18(18) . . ? O1 C1 Fe 179.8(5) . . ? O2 C2 Fe 178.4(4) . . ? C4 C3 C7 108.7(4) . . ? C4 C3 Fe 70.2(3) . . ? C7 C3 Fe 70.1(3) . . ? C4 C3 H3 125(3) . . ? C7 C3 H3 126(3) . . ? Fe C3 H3 122(3) . . ? C3 C4 C5 107.4(4) . . ? C3 C4 Fe 71.1(2) . . ? C5 C4 Fe 70.4(2) . . ? C3 C4 H4 131(3) . . ? C5 C4 H4 122(3) . . ? Fe C4 H4 122(3) . . ? C6 C5 C4 108.6(4) . . ? C6 C5 Fe 70.5(2) . . ? C4 C5 Fe 70.1(2) . . ? C6 C5 H5 126(2) . . ? C4 C5 H5 126(2) . . ? Fe C5 H5 120(2) . . ? C5 C6 C7 107.6(4) . . ? C5 C6 Fe 70.8(2) . . ? C7 C6 Fe 70.2(3) . . ? C5 C6 H6 130(3) . . ? C7 C6 H6 122(3) . . ? Fe C6 H6 128(3) . . ? C3 C7 C6 107.7(4) . . ? C3 C7 Fe 71.0(3) . . ? C6 C7 Fe 70.2(3) . . ? C3 C7 H7 121(3) . . ? C6 C7 H7 131(3) . . ? Fe C7 H7 130(3) . . ? C9 C8 Fe 179.4(3) . . ? C8 C9 C10 177.7(4) . . ? C14 C10 C11 115.7(3) . . ? C14 C10 C9 122.4(3) . . ? C11 C10 C9 122.0(3) . . ? C10 C11 C12 118.9(4) . . ? C10 C11 H11 121(3) . . ? C12 C11 H11 120(3) . . ? N C12 C11 125.3(5) . . ? N C12 H12 124(4) . . ? C11 C12 H12 111(4) . . ? N C13 C14 125.5(5) . . ? N C13 H13 123(2) . . ? C14 C13 H13 112(3) . . ? C13 C14 C10 119.5(5) . . ? C13 C14 H14 123(2) . . ? C10 C14 H14 118(2) . . ? C13 N C12 115.1(4) . . ? 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 Fe C2 1.761(4) . ? Fe C1 1.766(5) . ? Fe C8 1.906(3) . ? Fe C4 2.087(4) . ? Fe C6 2.087(4) . ? Fe C7 2.087(5) . ? Fe C5 2.091(4) . ? Fe C3 2.098(5) . ? C1 O1 1.131(5) . ? C2 O2 1.124(4) . ? C3 C4 1.389(6) . ? C3 C7 1.394(6) . ? C3 H3 0.86(4) . ? C4 C5 1.410(6) . ? C4 H4 0.80(4) . ? C5 C6 1.385(6) . ? C5 H5 0.93(4) . ? C6 C7 1.414(6) . ? C6 H6 0.94(4) . ? C7 H7 0.85(4) . ? C8 C9 1.203(4) . ? C9 C10 1.422(4) . ? C10 C14 1.382(5) . ? C10 C11 1.383(5) . ? C11 C12 1.386(6) . ? C11 H11 0.85(4) . ? C12 N 1.304(7) . ? C12 H12 0.79(4) . ? C13 N 1.303(7) . ? C13 C14 1.371(6) . ? C13 H13 0.82(3) . ? C14 H14 0.83(3) . ?