#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:01:24 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268859 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060615.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_7060615 loop_ _publ_author_name 'Bera, Pradip' 'Aher, Abhishek' 'Brandao, Paula' 'Manna, Sunil Kumar' 'Bhattacharyya, Indranil' 'Mondal, Gopinath' 'Jana, Abhimanyu' 'Santra, Ananyakumari' 'Bera, Pulakesh' _publ_section_title ; Anticancer activity, DNA binding and docking study of M(ii)-complexes (M = Zn, Cu and Ni) derived from a new pyrazine--thiazole ligand: synthesis, structure and DFT ; _journal_issue 27 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11999 _journal_page_last 12015 _journal_paper_doi 10.1039/D0NJ05883A _journal_volume 45 _journal_year 2021 _chemical_formula_sum 'C16 H12 N6 S' _chemical_formula_weight 320.38 _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 mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-10-22 deposited with the CCDC. 2021-04-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.024(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9257(6) _cell_length_b 17.9072(12) _cell_length_c 10.7961(7) _cell_measurement_reflns_used 440 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.16 _cell_measurement_theta_min 2.98 _cell_volume 1531.30(18) _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_unetI/netI 0.0336 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 22452 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.174 _diffrn_reflns_theta_min 2.204 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.7139 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.357 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 4127 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.4377P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0929 _refine_ls_wR_factor_ref 0.1018 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3265 _reflns_number_total 4127 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj05883a2.cif _cod_data_source_block f _cod_depositor_comments 'Adding full bibliography for 7060615--7060617.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060615 _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 0.917 _shelx_estimated_absorpt_t_max 0.957 _shelxl_version_number 2013-4 _shelx_res_file ; TITL f.res in P2(1)/n d=40mm t=10s CELL 0.71073 7.9257 17.9072 10.7961 90.000 92.024 90.000 ZERR 4.000 0.0006 0.0012 0.0007 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N S UNIT 64 48 24 4 TEMP -123.160 SIZE 0.20 0.30 0.40 L.S. 100 ACTA BOND BOND $H HTAB FMAP 2 PLAN 20 WGHT 0.047700 0.437700 FVAR 0.81028 S1 4 0.431878 0.583879 0.278090 11.00000 0.04381 0.01744 = 0.02010 -0.00034 0.01230 -0.00164 N1 3 0.559376 0.903708 0.450625 11.00000 0.04008 0.01833 = 0.02637 -0.00220 0.01286 -0.00128 N2 3 0.728454 0.862443 0.237120 11.00000 0.02526 0.02085 = 0.01930 0.00116 0.00501 -0.00104 N3 3 0.462206 0.711907 0.435072 11.00000 0.02279 0.01696 = 0.01940 0.00165 0.00498 -0.00045 N4 3 0.388461 0.654743 0.496024 11.00000 0.02916 0.01745 = 0.01949 -0.00186 0.00903 -0.00387 H4 2 0.343598 0.657372 0.568722 11.00000 0.03160 N5 3 0.291806 0.531270 0.473087 11.00000 0.02344 0.01709 = 0.01968 -0.00182 0.00456 -0.00002 N6 3 -0.062959 0.139997 0.541321 11.00000 0.04556 0.03303 = 0.03483 0.00873 0.00106 -0.01067 C1 1 0.632877 0.954102 0.377906 11.00000 0.05026 0.01646 = 0.03140 -0.00184 0.01576 -0.00191 AFIX 43 H1 2 0.628678 1.005369 0.400218 11.00000 -1.20000 AFIX 0 C2 1 0.714491 0.934143 0.271703 11.00000 0.03531 0.01979 = 0.02577 0.00288 0.00814 -0.00280 AFIX 43 H2 2 0.761773 0.972048 0.222066 11.00000 -1.20000 AFIX 0 C3 1 0.656266 0.812283 0.309029 11.00000 0.02289 0.01757 = 0.01813 -0.00123 0.00336 0.00024 AFIX 43 H3 2 0.664299 0.760908 0.288096 11.00000 -1.20000 AFIX 0 C4 1 0.568779 0.832390 0.414543 11.00000 0.02287 0.01742 = 0.01692 -0.00095 0.00283 -0.00010 C5 1 0.484917 0.775206 0.489787 11.00000 0.02127 0.01834 = 0.01745 0.00021 0.00462 0.00159 C6 1 0.433637 0.794579 0.618363 11.00000 0.03432 0.02283 = 0.01945 -0.00182 0.00943 -0.00046 AFIX 137 H6A 2 0.312777 0.806232 0.617146 11.00000 -1.50000 H6B 2 0.498124 0.838071 0.648271 11.00000 -1.50000 H6C 2 0.456524 0.752083 0.673632 11.00000 -1.50000 AFIX 0 C7 1 0.365063 0.590049 0.429679 11.00000 0.02111 0.01828 = 0.01827 -0.00056 0.00464 0.00286 C8 1 0.353479 0.493929 0.273034 11.00000 0.04077 0.01635 = 0.02130 -0.00247 0.00715 -0.00030 AFIX 43 H8 2 0.357428 0.461718 0.203278 11.00000 -1.20000 AFIX 0 C9 1 0.285318 0.475619 0.382759 11.00000 0.02369 0.01703 = 0.01979 -0.00027 0.00287 0.00196 C10 1 0.207632 0.403723 0.413802 11.00000 0.02143 0.01771 = 0.01913 0.00080 0.00066 0.00108 C11 1 0.228326 0.340539 0.339293 11.00000 0.02553 0.02119 = 0.01862 -0.00067 0.00303 -0.00051 AFIX 43 H11 2 0.290861 0.344443 0.266106 11.00000 -1.20000 AFIX 0 C12 1 0.159017 0.272626 0.370810 11.00000 0.02807 0.01968 = 0.02235 -0.00143 -0.00017 -0.00097 AFIX 43 H12 2 0.175606 0.229997 0.320295 11.00000 -1.20000 AFIX 0 C13 1 0.064557 0.266855 0.477094 11.00000 0.02319 0.02248 = 0.02135 0.00469 -0.00302 -0.00229 C14 1 0.039114 0.329701 0.550427 11.00000 0.02668 0.02844 = 0.01862 0.00301 0.00390 -0.00164 AFIX 43 H14 2 -0.027320 0.326076 0.621720 11.00000 -1.20000 AFIX 0 C15 1 0.110721 0.397383 0.519282 11.00000 0.02748 0.02289 = 0.02095 -0.00206 0.00297 -0.00024 AFIX 43 H15 2 0.093945 0.439927 0.569954 11.00000 -1.20000 AFIX 0 C16 1 -0.005783 0.195822 0.512212 11.00000 0.02959 0.02809 = 0.02290 0.00469 -0.00152 -0.00363 HKLF 4 REM f.res in P2(1)/n d=40mm t=10s REM R1 = 0.0385 for 3265 Fo > 4sig(Fo) and 0.0533 for all 4127 data REM 213 parameters refined using 0 restraints END WGHT 0.0475 0.4413 REM Instructions for potential hydrogen bonds EQIV $1 x-1/2, -y+3/2, z+1/2 HTAB N4 N2_$1 EQIV $2 x+1/2, -y+1/2, z-1/2 HTAB C8 N6_$2 REM Highest difference peak 0.357, deepest hole -0.279, 1-sigma level 0.050 Q1 1 0.6031 0.8228 0.3566 11.00000 0.05 0.36 Q2 1 0.2916 0.5000 0.4280 11.00000 0.05 0.33 Q3 1 0.2603 0.4401 0.3974 11.00000 0.05 0.30 Q4 1 0.5106 0.8051 0.4464 11.00000 0.05 0.30 Q5 1 0.3863 0.5863 0.3575 11.00000 0.05 0.29 Q6 1 0.2691 0.4898 0.3180 11.00000 0.05 0.29 Q7 1 0.4462 0.7854 0.5469 11.00000 0.05 0.29 Q8 1 0.3716 0.5375 0.2656 11.00000 0.05 0.29 Q9 1 0.2128 0.3726 0.3782 11.00000 0.05 0.29 Q10 1 0.1245 0.2713 0.4311 11.00000 0.05 0.28 Q11 1 0.0611 0.3619 0.5186 11.00000 0.05 0.28 Q12 1 0.0844 0.2929 0.5252 11.00000 0.05 0.27 Q13 1 0.6427 0.9227 0.4245 11.00000 0.05 0.26 Q14 1 0.2203 0.3051 0.3794 11.00000 0.05 0.26 Q15 1 0.1936 0.3944 0.4778 11.00000 0.05 0.25 Q16 1 0.7148 0.9376 0.3426 11.00000 0.05 0.24 Q17 1 0.0499 0.3004 0.4948 11.00000 0.05 0.24 Q18 1 0.4126 0.6876 0.4599 11.00000 0.05 0.23 Q19 1 0.7212 0.8379 0.2958 11.00000 0.05 0.23 Q20 1 0.6549 0.8394 0.2651 11.00000 0.05 0.22 ; _shelx_res_checksum 50587 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 S1 S 0.43188(5) 0.58388(2) 0.27809(3) 0.02685(11) Uani 1 1 d . . . . . N1 N 0.55938(17) 0.90371(6) 0.45063(12) 0.0280(3) Uani 1 1 d . . . . . N2 N 0.72845(15) 0.86244(6) 0.23712(11) 0.0217(2) Uani 1 1 d . . . . . N3 N 0.46221(14) 0.71191(6) 0.43507(10) 0.0196(2) Uani 1 1 d . . . . . N4 N 0.38846(15) 0.65474(6) 0.49602(11) 0.0218(2) Uani 1 1 d . . . . . H4 H 0.344(2) 0.6574(9) 0.5687(17) 0.032(5) Uiso 1 1 d . . . . . N5 N 0.29181(14) 0.53127(6) 0.47309(10) 0.0200(2) Uani 1 1 d . . . . . N6 N -0.06296(19) 0.14000(8) 0.54132(13) 0.0378(3) Uani 1 1 d . . . . . C1 C 0.6329(2) 0.95410(8) 0.37791(15) 0.0324(4) Uani 1 1 d . . . . . H1 H 0.6287 1.0054 0.4002 0.039 Uiso 1 1 calc R U . . . C2 C 0.71449(19) 0.93414(8) 0.27170(14) 0.0268(3) Uani 1 1 d . . . . . H2 H 0.7618 0.9720 0.2221 0.032 Uiso 1 1 calc R U . . . C3 C 0.65627(17) 0.81228(7) 0.30903(12) 0.0195(3) Uani 1 1 d . . . . . H3 H 0.6643 0.7609 0.2881 0.023 Uiso 1 1 calc R U . . . C4 C 0.56878(17) 0.83239(7) 0.41454(12) 0.0190(3) Uani 1 1 d . . . . . C5 C 0.48492(17) 0.77521(7) 0.48979(12) 0.0189(3) Uani 1 1 d . . . . . C6 C 0.43364(19) 0.79458(8) 0.61836(13) 0.0253(3) Uani 1 1 d . . . . . H6A H 0.3128 0.8062 0.6171 0.038 Uiso 1 1 calc R U . . . H6B H 0.4981 0.8381 0.6483 0.038 Uiso 1 1 calc R U . . . H6C H 0.4565 0.7521 0.6736 0.038 Uiso 1 1 calc R U . . . C7 C 0.36506(17) 0.59005(7) 0.42968(12) 0.0191(3) Uani 1 1 d . . . . . C8 C 0.3535(2) 0.49393(7) 0.27303(13) 0.0260(3) Uani 1 1 d . . . . . H8 H 0.3574 0.4617 0.2033 0.031 Uiso 1 1 calc R U . . . C9 C 0.28532(17) 0.47562(7) 0.38276(12) 0.0201(3) Uani 1 1 d . . . . . C10 C 0.20763(17) 0.40372(7) 0.41380(12) 0.0194(3) Uani 1 1 d . . . . . C11 C 0.22833(18) 0.34054(7) 0.33929(13) 0.0217(3) Uani 1 1 d . . . . . H11 H 0.2909 0.3444 0.2661 0.026 Uiso 1 1 calc R U . . . C12 C 0.15902(18) 0.27263(8) 0.37081(13) 0.0234(3) Uani 1 1 d . . . . . H12 H 0.1756 0.2300 0.3203 0.028 Uiso 1 1 calc R U . . . C13 C 0.06456(17) 0.26685(8) 0.47709(13) 0.0224(3) Uani 1 1 d . . . . . C14 C 0.03911(18) 0.32970(8) 0.55043(13) 0.0245(3) Uani 1 1 d . . . . . H14 H -0.0273 0.3261 0.6217 0.029 Uiso 1 1 calc R U . . . C15 C 0.11072(18) 0.39738(8) 0.51928(13) 0.0237(3) Uani 1 1 d . . . . . H15 H 0.0939 0.4399 0.5700 0.028 Uiso 1 1 calc R U . . . C16 C -0.00578(19) 0.19582(8) 0.51221(14) 0.0269(3) 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 S1 0.0438(2) 0.01744(17) 0.02010(18) -0.00034(12) 0.01230(15) -0.00164(14) N1 0.0401(7) 0.0183(6) 0.0264(7) -0.0022(5) 0.0129(5) -0.0013(5) N2 0.0253(6) 0.0209(6) 0.0193(6) 0.0012(4) 0.0050(4) -0.0010(4) N3 0.0228(6) 0.0170(5) 0.0194(6) 0.0017(4) 0.0050(4) -0.0004(4) N4 0.0292(6) 0.0175(6) 0.0195(6) -0.0019(4) 0.0090(5) -0.0039(4) N5 0.0234(6) 0.0171(5) 0.0197(6) -0.0018(4) 0.0046(4) 0.0000(4) N6 0.0456(8) 0.0330(8) 0.0348(8) 0.0087(6) 0.0011(6) -0.0107(6) C1 0.0503(10) 0.0165(7) 0.0314(8) -0.0018(6) 0.0158(7) -0.0019(6) C2 0.0353(8) 0.0198(7) 0.0258(7) 0.0029(5) 0.0081(6) -0.0028(6) C3 0.0229(6) 0.0176(6) 0.0181(6) -0.0012(5) 0.0034(5) 0.0002(5) C4 0.0229(7) 0.0174(6) 0.0169(6) -0.0010(5) 0.0028(5) -0.0001(5) C5 0.0213(6) 0.0183(6) 0.0174(6) 0.0002(5) 0.0046(5) 0.0016(5) C6 0.0343(8) 0.0228(7) 0.0195(7) -0.0018(5) 0.0094(6) -0.0005(6) C7 0.0211(6) 0.0183(6) 0.0183(6) -0.0006(5) 0.0046(5) 0.0029(5) C8 0.0408(9) 0.0164(6) 0.0213(7) -0.0025(5) 0.0071(6) -0.0003(6) C9 0.0237(7) 0.0170(6) 0.0198(6) -0.0003(5) 0.0029(5) 0.0020(5) C10 0.0214(6) 0.0177(6) 0.0191(6) 0.0008(5) 0.0007(5) 0.0011(5) C11 0.0255(7) 0.0212(7) 0.0186(6) -0.0007(5) 0.0030(5) -0.0005(5) C12 0.0281(7) 0.0197(7) 0.0224(7) -0.0014(5) -0.0002(5) -0.0010(5) C13 0.0232(7) 0.0225(7) 0.0214(7) 0.0047(5) -0.0030(5) -0.0023(5) C14 0.0267(7) 0.0284(7) 0.0186(7) 0.0030(5) 0.0039(5) -0.0016(6) C15 0.0275(7) 0.0229(7) 0.0210(7) -0.0021(5) 0.0030(5) -0.0002(5) C16 0.0296(7) 0.0281(8) 0.0229(7) 0.0047(6) -0.0015(6) -0.0036(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 '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 C8 S1 C7 88.16(7) . . ? C4 N1 C1 116.20(12) . . ? C3 N2 C2 116.24(12) . . ? C5 N3 N4 119.74(11) . . ? N3 N4 C7 115.83(11) . . ? N3 N4 H4 126.1(11) . . ? C7 N4 H4 117.6(11) . . ? C7 N5 C9 109.46(11) . . ? N1 C1 C2 122.44(13) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? N2 C2 C1 121.54(13) . . ? N2 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? N2 C3 C4 122.44(12) . . ? N2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? N1 C4 C3 121.07(12) . . ? N1 C4 C5 118.04(12) . . ? C3 C4 C5 120.89(12) . . ? N3 C5 C4 114.56(11) . . ? N3 C5 C6 126.13(12) . . ? C4 C5 C6 119.31(11) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N5 C7 N4 123.41(12) . . ? N5 C7 S1 116.28(10) . . ? N4 C7 S1 120.30(10) . . ? C9 C8 S1 110.56(10) . . ? C9 C8 H8 124.7 . . ? S1 C8 H8 124.7 . . ? C8 C9 N5 115.55(12) . . ? C8 C9 C10 126.31(12) . . ? N5 C9 C10 118.15(12) . . ? C15 C10 C11 118.69(12) . . ? C15 C10 C9 120.15(12) . . ? C11 C10 C9 121.17(12) . . ? C12 C11 C10 120.91(13) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.80(13) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 119.96(13) . . ? C14 C13 C16 119.77(13) . . ? C12 C13 C16 120.27(13) . . ? C15 C14 C13 119.98(13) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 120.64(13) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? N6 C16 C13 179.00(18) . . ? 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 S1 C8 1.7266(14) . ? S1 C7 1.7413(14) . ? N1 C4 1.3380(17) . ? N1 C1 1.3425(19) . ? N2 C3 1.3297(17) . ? N2 C2 1.3428(18) . ? N3 C5 1.2879(17) . ? N3 N4 1.3600(15) . ? N4 C7 1.3712(17) . ? N4 H4 0.874(18) . ? N5 C7 1.2976(17) . ? N5 C9 1.3940(17) . ? N6 C16 1.1461(19) . ? C1 C2 1.383(2) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.4014(18) . ? C3 H3 0.9500 . ? C4 C5 1.4793(18) . ? C5 C6 1.5008(19) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 C9 1.3594(19) . ? C8 H8 0.9500 . ? C9 C10 1.4709(18) . ? C10 C15 1.4005(19) . ? C10 C11 1.4012(18) . ? C11 C12 1.3819(19) . ? C11 H11 0.9500 . ? C12 C13 1.396(2) . ? C12 H12 0.9500 . ? C13 C14 1.395(2) . ? C13 C16 1.4448(19) . ? C14 C15 1.3848(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ?