#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:37:36 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271183 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061015.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_7061015 loop_ _publ_author_name 'Saha, Urmila' 'Mabhai, Subhabrata' 'Das, Bhriguram' 'Kumar, Gopinatha Suresh' 'Brand\~ao, Paula' 'Dolai, Malay' _publ_section_title ; Combined theoretical and experimental investigation of a DNA interactive poly-hydroxyl enamine tautomer exhibiting “turn on” sensing for Zn2+ in pseudo-aqueous medium ; _journal_issue 44 _journal_name_full 'New Journal of Chemistry' _journal_page_first 20806 _journal_page_last 20817 _journal_paper_doi 10.1039/D1NJ03510J _journal_volume 45 _journal_year 2021 _chemical_formula_sum 'C12 H16 Br N O5' _chemical_formula_weight 334.17 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-06-26 deposited with the CCDC. 2021-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.998(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2787(16) _cell_length_b 10.7136(13) _cell_length_c 10.6360(14) _cell_measurement_reflns_used 432 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.12 _cell_measurement_theta_min 3.02 _cell_volume 1330.7(3) _computing_cell_refinement 'Bruker Smart' _computing_data_collection 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_publication_material 'SHELXL-2016/4 (Sheldrick, 2016)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _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 0.0545 _diffrn_reflns_av_unetI/netI 0.0557 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 15131 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.144 _diffrn_reflns_theta_min 1.744 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 3.105 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.6225 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.668 _exptl_crystal_description plate _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.435 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 3589 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0370 _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^)+(0.0267P)^2^+0.5203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0717 _refine_ls_wR_factor_ref 0.0789 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2701 _reflns_number_total 3589 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03510j2.cif _cod_data_source_block f _cod_depositor_comments 'Adding full bibliography for 7061015.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7061015 _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 0.605 _shelx_estimated_absorpt_t_max 0.913 _shelx_res_file ; TITL f.res in P2(1)/c d=40mm t=20s f.res created by SHELXL-2018/3 at 18:25:42 on 26-May-2021 CELL 0.71073 12.2787 10.7136 10.6360 90.000 107.998 90.000 ZERR 4.000 0.0016 0.0013 0.0014 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O BR UNIT 48 64 4 20 4 TEMP -123.140 SIZE 0.03 0.16 0.18 L.S. 100 ACTA BOND BOND $H HTAB FMAP 2 PLAN 20 omit 0 2 0 WGHT 0.026700 0.520300 FVAR 0.52780 BR 5 -0.044416 0.486877 0.811006 11.00000 0.02566 0.02461 = 0.03947 0.00437 0.02086 -0.00210 O1 4 0.297524 0.597879 0.526750 11.00000 0.02054 0.01576 = 0.02099 -0.00349 0.01132 -0.00282 O2 4 0.200142 0.376634 0.494557 11.00000 0.03000 0.01376 = 0.02582 -0.00839 0.01268 -0.00647 dfix 0.90 0.01 O3 H3a O4 H4a O5 H5a O3 4 0.550557 0.774920 0.603971 11.00000 0.02496 0.01202 = 0.02136 0.00163 0.01216 0.00388 H3A 2 0.589533 0.705507 0.634369 11.00000 0.04436 O4 4 0.463701 1.102464 0.623146 11.00000 0.04171 0.01179 = 0.02219 0.00124 0.01367 -0.00581 H4A 2 0.450902 1.148139 0.550838 11.00000 0.05121 O5 4 0.353104 1.042193 0.837288 11.00000 0.02361 0.01321 = 0.02178 -0.00069 0.01383 0.00023 H5A 2 0.323518 1.011655 0.896954 11.00000 0.05132 N1 3 0.357855 0.795415 0.674825 11.00000 0.01743 0.00945 = 0.01778 -0.00227 0.00772 -0.00109 H1 2 0.365929 0.746314 0.619680 11.00000 0.02143 C1 1 0.229910 0.572950 0.594956 11.00000 0.01467 0.01352 = 0.01678 0.00100 0.00415 0.00135 C2 1 0.169772 0.455323 0.578713 11.00000 0.01796 0.01343 = 0.01687 -0.00158 0.00269 -0.00130 C3 1 0.091834 0.430591 0.642968 11.00000 0.01704 0.01446 = 0.02470 0.00222 0.00462 -0.00249 AFIX 43 H3 2 0.051082 0.353847 0.628176 11.00000 -1.20000 AFIX 0 C4 1 0.071708 0.519368 0.731723 11.00000 0.01764 0.01840 = 0.02249 0.00296 0.01051 -0.00045 C5 1 0.132129 0.627182 0.759615 11.00000 0.02090 0.01485 = 0.02357 0.00015 0.01105 0.00096 AFIX 43 H5 2 0.120579 0.683426 0.823372 11.00000 -1.20000 AFIX 0 C6 1 0.213034 0.655383 0.692536 11.00000 0.01451 0.01207 = 0.01947 0.00110 0.00641 0.00070 C7 1 0.148957 0.255799 0.475238 11.00000 0.04258 0.01629 = 0.03807 -0.01085 0.01571 -0.00863 AFIX 137 H7A 2 0.168433 0.211739 0.560048 11.00000 -1.50000 H7B 2 0.177665 0.208392 0.413257 11.00000 -1.50000 H7C 2 0.065596 0.264223 0.439131 11.00000 -1.50000 AFIX 0 C8 1 0.280966 0.764581 0.729218 11.00000 0.01887 0.01106 = 0.02021 -0.00144 0.00713 0.00114 AFIX 43 H8 2 0.269529 0.816903 0.796149 11.00000 -1.20000 AFIX 0 C9 1 0.436861 0.902357 0.707200 11.00000 0.01597 0.00931 = 0.01355 0.00011 0.00566 -0.00208 C10 1 0.556029 0.853671 0.714455 11.00000 0.01780 0.01435 = 0.01929 -0.00193 0.00824 -0.00149 AFIX 23 H10A 2 0.607445 0.925110 0.715507 11.00000 -1.20000 H10B 2 0.588309 0.806099 0.797463 11.00000 -1.20000 AFIX 0 C11 1 0.391095 0.996204 0.594378 11.00000 0.02229 0.01379 = 0.01538 0.00099 0.00650 0.00132 AFIX 23 H11A 2 0.391170 0.958655 0.509356 11.00000 -1.20000 H11B 2 0.311624 1.020400 0.587390 11.00000 -1.20000 AFIX 0 C12 1 0.446610 0.960627 0.841118 11.00000 0.01906 0.01045 = 0.01750 -0.00048 0.00670 -0.00075 AFIX 23 H12A 2 0.449912 0.893193 0.905831 11.00000 -1.20000 H12B 2 0.519102 1.008263 0.872121 11.00000 -1.20000 AFIX 0 HKLF 4 REM f.res in P2(1)/c d=40mm t=20s REM wR2 = 0.0789, GooF = S = 1.020, Restrained GooF = 1.020 for all data REM R1 = 0.0370 for 2701 Fo > 4sig(Fo) and 0.0583 for all 3589 data REM 189 parameters refined using 3 restraints END WGHT 0.0267 0.5202 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y-1/2, -z+3/2 HTAB O3 O5_$1 EQIV $2 -x+1, -y+2, -z+1 HTAB O4 O3_$2 EQIV $3 x, -y+3/2, z+1/2 HTAB O5 O1_$3 HTAB O5 O2_$3 HTAB N1 O1 EQIV $4 x, -y+1/2, z-1/2 HTAB C7 Br_$4 HTAB C8 O1_$3 HTAB C8 O5 HTAB C10 O4_$1 HTAB C12 O1_$3 EQIV $5 -x+1, y+1/2, -z+3/2 HTAB C12 O1_$5 REM Highest difference peak 0.435, deepest hole -0.592, 1-sigma level 0.090 Q1 1 0.2202 0.6209 0.6386 11.00000 0.05 0.43 Q2 1 0.4956 0.8902 0.7064 11.00000 0.05 0.43 Q3 1 -0.0387 0.4297 0.7577 11.00000 0.05 0.43 Q4 1 0.0060 0.5010 0.8858 11.00000 0.05 0.42 Q5 1 0.4195 0.9499 0.6568 11.00000 0.05 0.40 Q6 1 0.2177 0.5037 0.6210 11.00000 0.05 0.40 Q7 1 0.1970 0.5164 0.5809 11.00000 0.05 0.39 Q8 1 0.1598 0.6356 0.7069 11.00000 0.05 0.38 Q9 1 0.0803 0.4855 0.6647 11.00000 0.05 0.37 Q10 1 0.3238 0.6368 0.5749 11.00000 0.05 0.34 Q11 1 0.1798 0.4252 0.5320 11.00000 0.05 0.33 Q12 1 0.1231 0.4349 0.5979 11.00000 0.05 0.33 Q13 1 0.0422 0.4219 0.8774 11.00000 0.05 0.33 Q14 1 0.0236 0.4874 0.7962 11.00000 0.05 0.33 Q15 1 0.5635 0.8066 0.6578 11.00000 0.05 0.32 Q16 1 0.1684 0.3212 0.4931 11.00000 0.05 0.32 Q17 1 0.0799 0.5924 0.7188 11.00000 0.05 0.32 Q18 1 0.5183 0.7336 0.6595 11.00000 0.05 0.31 Q19 1 0.4515 0.9303 0.7616 11.00000 0.05 0.31 Q20 1 0.0805 0.3962 0.6437 11.00000 0.05 0.31 ; _shelx_res_checksum 324 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br Br -0.04442(2) 0.48688(2) 0.81101(3) 0.02745(9) Uani 1 1 d . . . . . O1 O 0.29752(14) 0.59788(13) 0.52675(17) 0.0180(4) Uani 1 1 d . . . . . O2 O 0.20014(15) 0.37663(14) 0.49456(18) 0.0223(4) Uani 1 1 d . . . . . O3 O 0.55056(15) 0.77492(14) 0.60397(17) 0.0183(4) Uani 1 1 d D . . . . H3A H 0.590(2) 0.7055(17) 0.634(3) 0.044(9) Uiso 1 1 d D . . . . O4 O 0.46370(17) 1.10246(14) 0.62315(18) 0.0244(4) Uani 1 1 d D . . . . H4A H 0.451(3) 1.148(3) 0.551(2) 0.051(10) Uiso 1 1 d D . . . . O5 O 0.35310(14) 1.04219(13) 0.83729(17) 0.0180(4) Uani 1 1 d D . . . . H5A H 0.324(3) 1.012(2) 0.897(3) 0.051(10) Uiso 1 1 d D . . . . N1 N 0.35786(17) 0.79542(16) 0.6748(2) 0.0144(4) Uani 1 1 d . . . . . H1 H 0.366(2) 0.746(2) 0.620(3) 0.021(7) Uiso 1 1 d . . . . . C1 C 0.2299(2) 0.57295(19) 0.5950(2) 0.0151(5) Uani 1 1 d . . . . . C2 C 0.1698(2) 0.45532(19) 0.5787(2) 0.0167(5) Uani 1 1 d . . . . . C3 C 0.0918(2) 0.4306(2) 0.6430(3) 0.0192(5) Uani 1 1 d . . . . . H3 H 0.051082 0.353847 0.628176 0.023 Uiso 1 1 calc R U . . . C4 C 0.0717(2) 0.5194(2) 0.7317(3) 0.0185(5) Uani 1 1 d . . . . . C5 C 0.1321(2) 0.6272(2) 0.7596(3) 0.0188(5) Uani 1 1 d . . . . . H5 H 0.120579 0.683426 0.823372 0.023 Uiso 1 1 calc R U . . . C6 C 0.2130(2) 0.65538(19) 0.6925(2) 0.0151(5) Uani 1 1 d . . . . . C7 C 0.1490(3) 0.2558(2) 0.4752(3) 0.0316(7) Uani 1 1 d . . . . . H7A H 0.168433 0.211739 0.560048 0.047 Uiso 1 1 calc R U . . . H7B H 0.177665 0.208392 0.413257 0.047 Uiso 1 1 calc R U . . . H7C H 0.065596 0.264223 0.439131 0.047 Uiso 1 1 calc R U . . . C8 C 0.2810(2) 0.76458(19) 0.7292(2) 0.0165(5) Uani 1 1 d . . . . . H8 H 0.269529 0.816903 0.796149 0.020 Uiso 1 1 calc R U . . . C9 C 0.43686(19) 0.90236(18) 0.7072(2) 0.0127(5) Uani 1 1 d . . . . . C10 C 0.5560(2) 0.8537(2) 0.7145(2) 0.0166(5) Uani 1 1 d . . . . . H10A H 0.607445 0.925110 0.715507 0.020 Uiso 1 1 calc R U . . . H10B H 0.588309 0.806099 0.797463 0.020 Uiso 1 1 calc R U . . . C11 C 0.3911(2) 0.99620(18) 0.5944(2) 0.0170(5) Uani 1 1 d . . . . . H11A H 0.391170 0.958655 0.509356 0.020 Uiso 1 1 calc R U . . . H11B H 0.311624 1.020400 0.587390 0.020 Uiso 1 1 calc R U . . . C12 C 0.4466(2) 0.96063(19) 0.8411(2) 0.0154(5) Uani 1 1 d . . . . . H12A H 0.449912 0.893193 0.905831 0.019 Uiso 1 1 calc R U . . . H12B H 0.519102 1.008263 0.872121 0.019 Uiso 1 1 calc R U . . . 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 Br 0.02566(16) 0.02461(14) 0.03947(18) 0.00437(11) 0.02086(13) -0.00210(10) O1 0.0205(10) 0.0158(8) 0.0210(10) -0.0035(6) 0.0113(8) -0.0028(6) O2 0.0300(11) 0.0138(8) 0.0258(10) -0.0084(7) 0.0127(9) -0.0065(7) O3 0.0250(10) 0.0120(8) 0.0214(10) 0.0016(6) 0.0122(8) 0.0039(6) O4 0.0417(12) 0.0118(8) 0.0222(11) 0.0012(7) 0.0137(9) -0.0058(7) O5 0.0236(10) 0.0132(8) 0.0218(10) -0.0007(6) 0.0138(8) 0.0002(6) N1 0.0174(11) 0.0095(8) 0.0178(11) -0.0023(8) 0.0077(9) -0.0011(7) C1 0.0147(12) 0.0135(10) 0.0168(13) 0.0010(9) 0.0042(10) 0.0013(8) C2 0.0180(13) 0.0134(10) 0.0169(13) -0.0016(9) 0.0027(11) -0.0013(8) C3 0.0170(13) 0.0145(10) 0.0247(14) 0.0022(9) 0.0046(11) -0.0025(9) C4 0.0176(13) 0.0184(11) 0.0225(14) 0.0030(9) 0.0105(11) -0.0005(9) C5 0.0209(14) 0.0149(11) 0.0236(14) 0.0001(9) 0.0111(12) 0.0010(9) C6 0.0145(12) 0.0121(10) 0.0195(13) 0.0011(8) 0.0064(11) 0.0007(8) C7 0.0426(19) 0.0163(12) 0.0381(18) -0.0108(11) 0.0157(15) -0.0086(11) C8 0.0189(13) 0.0111(10) 0.0202(14) -0.0014(8) 0.0071(11) 0.0011(8) C9 0.0160(12) 0.0093(9) 0.0135(12) 0.0001(8) 0.0057(10) -0.0021(8) C10 0.0178(13) 0.0144(10) 0.0193(14) -0.0019(8) 0.0082(11) -0.0015(8) C11 0.0223(13) 0.0138(10) 0.0154(12) 0.0010(9) 0.0065(10) 0.0013(9) C12 0.0191(13) 0.0105(10) 0.0175(13) -0.0005(8) 0.0067(11) -0.0008(8) 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' Br Br -0.2901 2.4595 '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 O2 C7 117.28(19) . . ? C10 O3 H3A 108(2) . . ? C11 O4 H4A 109(2) . . ? C12 O5 H5A 105(2) . . ? C8 N1 C9 127.86(19) . . ? C8 N1 H1 115.1(18) . . ? C9 N1 H1 116.9(18) . . ? O1 C1 C6 123.06(19) . . ? O1 C1 C2 120.6(2) . . ? C6 C1 C2 116.3(2) . . ? O2 C2 C3 125.9(2) . . ? O2 C2 C1 112.64(19) . . ? C3 C2 C1 121.5(2) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 121.5(2) . . ? C5 C4 Br 119.62(18) . . ? C3 C4 Br 118.88(17) . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C8 C6 C5 118.6(2) . . ? C8 C6 C1 120.3(2) . . ? C5 C6 C1 120.96(19) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C6 122.4(2) . . ? N1 C8 H8 118.8 . . ? C6 C8 H8 118.8 . . ? N1 C9 C12 113.14(17) . . ? N1 C9 C10 107.27(16) . . ? C12 C9 C10 107.10(19) . . ? N1 C9 C11 105.77(19) . . ? C12 C9 C11 111.50(17) . . ? C10 C9 C11 112.08(18) . . ? O3 C10 C9 110.94(19) . . ? O3 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? O4 C11 C9 107.66(19) . . ? O4 C11 H11A 110.2 . . ? C9 C11 H11A 110.2 . . ? O4 C11 H11B 110.2 . . ? C9 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? O5 C12 C9 113.07(19) . . ? O5 C12 H12A 109.0 . . ? C9 C12 H12A 109.0 . . ? O5 C12 H12B 109.0 . . ? C9 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? 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 Br C4 1.900(2) . ? O1 C1 1.288(3) . ? O2 C2 1.363(3) . ? O2 C7 1.426(3) . ? O3 C10 1.431(3) . ? O3 H3A 0.889(10) . ? O4 C11 1.420(3) . ? O4 H4A 0.884(10) . ? O5 C12 1.433(3) . ? O5 H5A 0.886(10) . ? N1 C8 1.293(3) . ? N1 C9 1.472(3) . ? N1 H1 0.82(3) . ? C1 C6 1.426(3) . ? C1 C2 1.444(3) . ? C2 C3 1.363(3) . ? C3 C4 1.415(3) . ? C3 H3 0.9500 . ? C4 C5 1.355(3) . ? C5 C6 1.423(3) . ? C5 H5 0.9500 . ? C6 C8 1.420(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8 0.9500 . ? C9 C12 1.526(3) . ? C9 C10 1.533(3) . ? C9 C11 1.533(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ?