#------------------------------------------------------------------------------ #$Date: 2020-05-23 07:17:49 +0300 (Sat, 23 May 2020) $ #$Revision: 252307 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240579.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_7240579 loop_ _publ_author_name 'Colombo Dugoni, Greta' 'Baggioli, Alberto' 'Famulari, Antonino' 'Sacchetti, Alessandro' 'Mart\'i-Rujas, Javier' 'Mariani, Mario' 'Macerata, Elena' 'Mossini, Eros' 'Mele, Andrea' _publ_section_title ; Structural properties of the chelating agent 2,6-bis(1-(3-hydroxypropyl)-1,2,3-triazol-4-yl)pyridine: a combined XRD and DFT structural study ; _journal_issue 33 _journal_name_full 'RSC Advances' _journal_page_first 19629 _journal_paper_doi 10.1039/D0RA04142D _journal_volume 10 _journal_year 2020 _chemical_formula_sum 'C15 H19 N7 O2' _chemical_formula_weight 329.37 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2020-02-14 deposited with the CCDC. 2020-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.985(3) _cell_length_b 7.6989(10) _cell_length_c 21.093(4) _cell_measurement_reflns_used 1021 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 64.88 _cell_measurement_theta_min 4.19 _cell_volume 3245.4(9) _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_Laue_measured_fraction_full 0.971 _diffrn_reflns_Laue_measured_fraction_max 0.971 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 9258 _diffrn_reflns_point_group_measured_fraction_full 0.971 _diffrn_reflns_point_group_measured_fraction_max 0.971 _diffrn_reflns_theta_full 66.072 _diffrn_reflns_theta_max 66.072 _diffrn_reflns_theta_min 4.192 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.784 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.348 _exptl_crystal_description block _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.156 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 2746 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0600P)^2^+0.3901P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1012 _refine_ls_wR_factor_ref 0.1062 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2372 _reflns_number_total 2746 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra04142d2.cif _cod_data_source_block PTD _cod_original_cell_volume 3245.3(9) _cod_database_code 7240579 _shelx_shelxl_version_number 2017/1 _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 0.859 _shelx_estimated_absorpt_t_max 0.891 _shelx_res_file ; TITL test in Pbca shelx.res created by SHELXL-2017/1 at 09:26:36 on 16-Jan-2019 CELL 1.54178 19.9846 7.6989 21.0928 90.000 90.000 90.000 ZERR 8.00 0.0034 0.0010 0.0037 0.000 0.000 0.000 LATT 1 SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 - X, - Y, 1/2 + Z SFAC C H N O UNIT 120 152 56 16 MERG 2 DFIX 0.820 0.020 O2 H2C FMAP 2 PLAN 10 SIZE 0.150 0.200 0.200 ACTA L.S. 6 TEMP 23.00 WGHT 0.060000 0.390100 FVAR 0.10176 N1 3 0.197009 0.233532 0.132975 11.00000 0.03596 0.05533 = 0.04680 -0.00222 0.00497 0.00297 N4 3 0.412204 0.131045 0.184593 11.00000 0.03933 0.04780 = 0.04272 -0.00432 -0.00107 -0.00120 N7 3 0.611246 0.089642 0.121146 11.00000 0.03763 0.06167 = 0.05071 -0.00605 -0.00427 0.00286 N5 3 0.588659 0.060938 0.219755 11.00000 0.04413 0.08112 = 0.05303 -0.00643 -0.00998 0.00729 N3 3 0.300880 0.228396 0.110286 11.00000 0.03729 0.07158 = 0.04527 0.00596 0.00378 0.00111 N2 3 0.241568 0.262651 0.086706 11.00000 0.04054 0.07750 = 0.04712 0.00800 0.00463 0.00337 O1 4 0.023018 0.256433 0.020520 11.00000 0.04543 0.12859 = 0.07353 0.04267 -0.00632 -0.01029 AFIX 83 H1 2 -0.015657 0.277319 0.010008 11.00000 -1.50000 AFIX 0 C1 1 0.023084 0.134798 0.070724 11.00000 0.04395 0.08030 = 0.06213 0.01435 -0.00192 -0.00842 AFIX 23 H1A 2 0.001332 0.028279 0.057364 11.00000 -1.20000 H1B 2 -0.001204 0.181263 0.106747 11.00000 -1.20000 AFIX 0 C2 1 0.094820 0.098200 0.089136 11.00000 0.04508 0.05771 = 0.06224 -0.00139 0.00018 0.00335 AFIX 23 H2A 2 0.096287 0.000100 0.117959 11.00000 -1.20000 H2B 2 0.120420 0.068323 0.051618 11.00000 -1.20000 AFIX 0 C3 1 0.125451 0.254716 0.120582 11.00000 0.03651 0.05748 = 0.05659 -0.00548 0.00192 0.00990 AFIX 23 H3A 2 0.118877 0.355371 0.093632 11.00000 -1.20000 H3B 2 0.102533 0.276317 0.160346 11.00000 -1.20000 AFIX 0 C4 1 0.227578 0.180318 0.185860 11.00000 0.04120 0.05942 = 0.04063 0.00032 0.00618 0.00161 AFIX 43 H4 2 0.207664 0.151062 0.224253 11.00000 -1.20000 AFIX 0 C5 1 0.294320 0.177958 0.171614 11.00000 0.03995 0.04722 = 0.04147 -0.00254 0.00375 -0.00129 C6 1 0.351459 0.126128 0.211335 11.00000 0.04105 0.04479 = 0.04288 -0.00502 0.00090 -0.00197 C10 1 0.464402 0.074504 0.219285 11.00000 0.04306 0.04379 = 0.04442 -0.00800 -0.00607 -0.00052 C11 1 0.529828 0.076267 0.187621 11.00000 0.03906 0.05013 = 0.04877 -0.00801 -0.00831 0.00237 C12 1 0.544467 0.094205 0.124695 11.00000 0.03747 0.06020 = 0.04830 -0.00489 -0.00747 0.00162 AFIX 43 H12 2 0.514368 0.106899 0.091389 11.00000 -1.20000 AFIX 0 C13 1 0.654218 0.104280 0.065040 11.00000 0.04253 0.06823 = 0.06431 -0.00087 0.00481 -0.00478 AFIX 23 H13A 2 0.684395 0.201810 0.070525 11.00000 -1.20000 H13B 2 0.626587 0.127560 0.028199 11.00000 -1.20000 AFIX 0 C14 1 0.694776 -0.058369 0.053328 11.00000 0.03811 0.08718 = 0.06250 -0.00388 0.00550 0.00713 AFIX 23 H14A 2 0.724059 -0.039313 0.017319 11.00000 -1.20000 H14B 2 0.722664 -0.080971 0.090051 11.00000 -1.20000 AFIX 0 C15 1 0.651818 -0.215077 0.040631 11.00000 0.06041 0.06734 = 0.06857 0.00454 0.01795 0.01091 AFIX 23 H15A 2 0.680471 -0.313754 0.031652 11.00000 -1.20000 H15B 2 0.626170 -0.241903 0.078425 11.00000 -1.20000 AFIX 0 N6 3 0.638386 0.069511 0.179191 11.00000 0.04081 0.08741 = 0.05750 -0.00849 -0.00997 0.00626 C7 1 0.341006 0.069051 0.273393 11.00000 0.05003 0.06332 = 0.04396 -0.00074 0.00486 -0.00236 AFIX 43 H7 2 0.298328 0.069343 0.290971 11.00000 -1.20000 AFIX 0 C8 1 0.395077 0.012424 0.307974 11.00000 0.06411 0.06625 = 0.04141 0.00384 -0.00112 -0.00249 AFIX 43 H8 2 0.389347 -0.026429 0.349367 11.00000 -1.20000 AFIX 0 C9 1 0.457708 0.013611 0.280946 11.00000 0.05644 0.05642 = 0.04594 -0.00257 -0.00922 0.00170 AFIX 43 H9 2 0.494769 -0.025507 0.303466 11.00000 -1.20000 AFIX 0 O2 4 0.607258 -0.190549 -0.010826 11.00000 0.04871 0.08521 = 0.06658 -0.01085 0.01640 -0.00815 H2C 2 0.629323 -0.208492 -0.044413 11.00000 0.10321 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM test in Pbca REM R1 = 0.0405 for 2372 Fo > 4sig(Fo) and 0.0459 for all 2746 data REM 221 parameters refined using 1 restraints END WGHT 0.0587 0.3954 REM Highest difference peak 0.156, deepest hole -0.259, 1-sigma level 0.055 Q1 1 0.7516 -0.1314 0.1346 11.00000 0.05 0.16 Q2 1 0.1076 0.3721 0.1364 11.00000 0.05 0.13 Q3 1 0.0009 0.2865 0.1205 11.00000 0.05 0.13 Q4 1 0.7119 -0.1739 0.0983 11.00000 0.05 0.13 Q5 1 0.1148 -0.1195 0.1984 11.00000 0.05 0.13 Q6 1 0.4268 0.3371 0.1693 11.00000 0.05 0.12 Q7 1 0.3889 -0.1386 0.2418 11.00000 0.05 0.12 Q8 1 0.2869 -0.1718 0.3174 11.00000 0.05 0.11 Q9 1 0.2954 -0.1039 0.3410 11.00000 0.05 0.11 Q10 1 0.3180 0.3348 0.2645 11.00000 0.05 0.11 ; _shelx_res_checksum 47668 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -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 N1 N 0.19701(6) 0.23353(16) 0.13298(6) 0.0460(3) Uani 1 1 d . . . . . N4 N 0.41220(6) 0.13105(15) 0.18459(5) 0.0433(3) Uani 1 1 d . . . . . N7 N 0.61125(6) 0.08964(17) 0.12115(6) 0.0500(3) Uani 1 1 d . . . . . N5 N 0.58866(7) 0.06094(19) 0.21976(6) 0.0594(4) Uani 1 1 d . . . . . N3 N 0.30088(6) 0.22840(18) 0.11029(6) 0.0514(3) Uani 1 1 d . . . . . N2 N 0.24157(6) 0.26265(18) 0.08671(6) 0.0551(3) Uani 1 1 d . . . . . O1 O 0.02302(6) 0.2564(2) 0.02052(6) 0.0825(5) Uani 1 1 d . . . . . H1 H -0.015657 0.277319 0.010008 0.124 Uiso 1 1 calc R U . . . C1 C 0.02308(8) 0.1348(3) 0.07072(8) 0.0621(4) Uani 1 1 d . . . . . H1A H 0.001332 0.028279 0.057364 0.075 Uiso 1 1 calc R U . . . H1B H -0.001204 0.181263 0.106747 0.075 Uiso 1 1 calc R U . . . C2 C 0.09482(7) 0.0982(2) 0.08914(8) 0.0550(4) Uani 1 1 d . . . . . H2A H 0.096287 0.000100 0.117959 0.066 Uiso 1 1 calc R U . . . H2B H 0.120420 0.068323 0.051618 0.066 Uiso 1 1 calc R U . . . C3 C 0.12545(7) 0.25472(19) 0.12058(7) 0.0502(4) Uani 1 1 d . . . . . H3A H 0.118877 0.355371 0.093632 0.060 Uiso 1 1 calc R U . . . H3B H 0.102533 0.276317 0.160346 0.060 Uiso 1 1 calc R U . . . C4 C 0.22758(7) 0.1803(2) 0.18586(7) 0.0471(3) Uani 1 1 d . . . . . H4 H 0.207664 0.151062 0.224253 0.057 Uiso 1 1 calc R U . . . C5 C 0.29432(7) 0.17796(18) 0.17161(6) 0.0429(3) Uani 1 1 d . . . . . C6 C 0.35146(7) 0.12613(17) 0.21133(6) 0.0429(3) Uani 1 1 d . . . . . C10 C 0.46440(7) 0.07450(17) 0.21929(7) 0.0438(3) Uani 1 1 d . . . . . C11 C 0.52983(7) 0.07627(18) 0.18762(7) 0.0460(3) Uani 1 1 d . . . . . C12 C 0.54447(7) 0.0942(2) 0.12469(7) 0.0487(4) Uani 1 1 d . . . . . H12 H 0.514368 0.106899 0.091389 0.058 Uiso 1 1 calc R U . . . C13 C 0.65422(8) 0.1043(2) 0.06504(8) 0.0584(4) Uani 1 1 d . . . . . H13A H 0.684395 0.201810 0.070525 0.070 Uiso 1 1 calc R U . . . H13B H 0.626587 0.127560 0.028199 0.070 Uiso 1 1 calc R U . . . C14 C 0.69478(8) -0.0584(2) 0.05333(8) 0.0626(4) Uani 1 1 d . . . . . H14A H 0.724059 -0.039313 0.017319 0.075 Uiso 1 1 calc R U . . . H14B H 0.722664 -0.080971 0.090051 0.075 Uiso 1 1 calc R U . . . C15 C 0.65182(9) -0.2151(2) 0.04063(9) 0.0654(5) Uani 1 1 d . . . . . H15A H 0.680471 -0.313754 0.031652 0.079 Uiso 1 1 calc R U . . . H15B H 0.626170 -0.241903 0.078425 0.079 Uiso 1 1 calc R U . . . N6 N 0.63839(7) 0.0695(2) 0.17919(7) 0.0619(4) Uani 1 1 d . . . . . C7 C 0.34101(8) 0.0691(2) 0.27339(7) 0.0524(4) Uani 1 1 d . . . . . H7 H 0.298328 0.069343 0.290971 0.063 Uiso 1 1 calc R U . . . C8 C 0.39508(9) 0.0124(2) 0.30797(7) 0.0573(4) Uani 1 1 d . . . . . H8 H 0.389347 -0.026429 0.349367 0.069 Uiso 1 1 calc R U . . . C9 C 0.45771(8) 0.0136(2) 0.28095(7) 0.0529(4) Uani 1 1 d . . . . . H9 H 0.494769 -0.025507 0.303466 0.064 Uiso 1 1 calc R U . . . O2 O 0.60726(6) -0.19055(17) -0.01083(6) 0.0668(3) Uani 1 1 d D . . . . H2C H 0.6293(11) -0.208(3) -0.0444(9) 0.103(8) Uiso 1 1 d 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 N1 0.0360(6) 0.0553(7) 0.0468(6) -0.0022(5) 0.0050(5) 0.0030(5) N4 0.0393(6) 0.0478(6) 0.0427(6) -0.0043(5) -0.0011(5) -0.0012(5) N7 0.0376(6) 0.0617(7) 0.0507(7) -0.0061(6) -0.0043(5) 0.0029(5) N5 0.0441(7) 0.0811(9) 0.0530(7) -0.0064(7) -0.0100(6) 0.0073(6) N3 0.0373(6) 0.0716(8) 0.0453(7) 0.0060(6) 0.0038(5) 0.0011(5) N2 0.0405(7) 0.0775(8) 0.0471(7) 0.0080(6) 0.0046(5) 0.0034(6) O1 0.0454(7) 0.1286(12) 0.0735(8) 0.0427(8) -0.0063(6) -0.0103(7) C1 0.0440(9) 0.0803(11) 0.0621(10) 0.0143(8) -0.0019(7) -0.0084(8) C2 0.0451(8) 0.0577(9) 0.0622(9) -0.0014(7) 0.0002(7) 0.0034(7) C3 0.0365(8) 0.0575(8) 0.0566(9) -0.0055(7) 0.0019(6) 0.0099(6) C4 0.0412(8) 0.0594(8) 0.0406(7) 0.0003(6) 0.0062(6) 0.0016(6) C5 0.0399(7) 0.0472(7) 0.0415(7) -0.0025(6) 0.0037(6) -0.0013(6) C6 0.0410(7) 0.0448(7) 0.0429(7) -0.0050(6) 0.0009(6) -0.0020(6) C10 0.0431(8) 0.0438(7) 0.0444(7) -0.0080(6) -0.0061(6) -0.0005(6) C11 0.0391(8) 0.0501(8) 0.0488(8) -0.0080(6) -0.0083(6) 0.0024(6) C12 0.0375(7) 0.0602(8) 0.0483(8) -0.0049(6) -0.0075(6) 0.0016(6) C13 0.0425(8) 0.0682(10) 0.0643(10) -0.0009(8) 0.0048(7) -0.0048(7) C14 0.0381(8) 0.0872(12) 0.0625(10) -0.0039(9) 0.0055(7) 0.0071(8) C15 0.0604(11) 0.0673(10) 0.0686(10) 0.0045(8) 0.0180(9) 0.0109(8) N6 0.0408(7) 0.0874(10) 0.0575(8) -0.0085(7) -0.0100(6) 0.0063(7) C7 0.0500(9) 0.0633(9) 0.0440(7) -0.0007(7) 0.0049(6) -0.0024(7) C8 0.0641(10) 0.0662(10) 0.0414(8) 0.0038(7) -0.0011(7) -0.0025(8) C9 0.0564(9) 0.0564(8) 0.0459(8) -0.0026(6) -0.0092(7) 0.0017(7) O2 0.0487(6) 0.0852(8) 0.0666(7) -0.0108(6) 0.0164(6) -0.0082(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C4 N1 N2 110.82(12) . . ? C4 N1 C3 129.07(13) . . ? N2 N1 C3 120.05(12) . . ? C6 N4 C10 117.66(12) . . ? C12 N7 N6 110.72(13) . . ? C12 N7 C13 128.87(13) . . ? N6 N7 C13 120.41(13) . . ? N6 N5 C11 108.94(13) . . ? N2 N3 C5 109.36(11) . . ? N3 N2 N1 106.89(11) . . ? O1 C1 C2 108.47(13) . . ? C3 C2 C1 110.46(13) . . ? N1 C3 C2 112.77(12) . . ? N1 C4 C5 105.46(12) . . ? N3 C5 C4 107.45(12) . . ? N3 C5 C6 123.05(12) . . ? C4 C5 C6 129.46(13) . . ? N4 C6 C7 122.64(13) . . ? N4 C6 C5 117.13(12) . . ? C7 C6 C5 120.20(13) . . ? N4 C10 C9 122.91(13) . . ? N4 C10 C11 116.08(13) . . ? C9 C10 C11 120.99(13) . . ? N5 C11 C12 107.90(13) . . ? N5 C11 C10 122.78(13) . . ? C12 C11 C10 129.31(13) . . ? N7 C12 C11 105.39(12) . . ? N7 C13 C14 112.47(14) . . ? C15 C14 C13 112.78(14) . . ? O2 C15 C14 112.84(15) . . ? N5 N6 N7 107.04(12) . . ? C8 C7 C6 118.66(14) . . ? C7 C8 C9 119.56(14) . . ? C8 C9 C10 118.56(14) . . ? 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 N1 C4 1.3362(19) . ? N1 N2 1.3401(17) . ? N1 C3 1.4629(18) . ? N4 C6 1.3391(18) . ? N4 C10 1.3465(18) . ? N7 C12 1.3371(18) . ? N7 N6 1.3480(18) . ? N7 C13 1.4665(19) . ? N5 N6 1.313(2) . ? N5 C11 1.3622(18) . ? N3 N2 1.3122(17) . ? N3 C5 1.3570(18) . ? O1 C1 1.414(2) . ? C1 C2 1.512(2) . ? C2 C3 1.506(2) . ? C4 C5 1.367(2) . ? C5 C6 1.4714(19) . ? C6 C7 1.396(2) . ? C10 C9 1.389(2) . ? C10 C11 1.468(2) . ? C11 C12 1.366(2) . ? C13 C14 1.512(2) . ? C14 C15 1.505(3) . ? C15 O2 1.417(2) . ? C7 C8 1.375(2) . ? C8 C9 1.375(2) . ?