#------------------------------------------------------------------------------ #$Date: 2016-02-18 15:37:37 +0000 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507718.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_1507718 loop_ _publ_author_name 'Niu, Liting' 'Yang, Haijun' 'Wang, Ruji' 'Fu, Hua' _publ_section_title ; Metal-free ortho C-H borylation of 2-phenoxypyridines under mild conditions. ; _journal_issue 10 _journal_name_full 'Organic letters' _journal_page_first 2618 _journal_page_last 2621 _journal_paper_doi 10.1021/ol300950r _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C17 H19 B Br N O3' _chemical_formula_sum 'C17 H19 B Br N O3' _chemical_formula_weight 376.05 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3840(3) _cell_length_b 11.9448(5) _cell_length_c 19.0988(6) _cell_measurement_reflns_used 4522 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.4 _cell_measurement_theta_min 3.1 _cell_volume 1684.52(11) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.0971 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 12111 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 3.24 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.453 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro (Oxford, 2011)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.240 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.024(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 3656 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0251 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+0.2475P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.0519 _reflns_number_gt 3420 _reflns_number_total 3656 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL exp_188 in P212121 #19 CELL 0.71073 7.3840 11.9448 19.0988 90 90 90 ZERR 4 0.0003 0.0005 0.0006 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H B Br N O UNIT 68 76 4 4 4 12 OMIT -2 54 OMIT 1 2 0 OMIT 0 1 8 L.S. 8 ACTA BOND $H FMAP 2 PLAN 2 WGHT 0.022600 0.247500 FVAR 0.16659 BR1 4 -0.026597 0.861148 0.124703 11.00000 0.02811 0.02953 = 0.01233 -0.00043 -0.00087 -0.01154 O1 6 0.472618 0.931382 0.392125 11.00000 0.01233 0.01219 = 0.02342 0.00529 -0.00115 -0.00049 O2 6 0.281001 1.079247 0.363369 11.00000 0.00943 0.00972 = 0.01692 0.00159 -0.00130 -0.00154 O3 6 0.154319 0.748497 0.424997 11.00000 0.02432 0.01093 = 0.02175 0.00497 -0.00389 -0.00071 N1 5 0.182584 0.936026 0.456346 11.00000 0.01156 0.01407 = 0.01525 0.00304 -0.00114 -0.00116 B1 3 0.285215 0.962130 0.380551 11.00000 0.01190 0.01224 = 0.01494 0.00210 0.00184 -0.00014 C1 1 0.582812 1.015949 0.359420 11.00000 0.01324 0.01241 = 0.02051 0.00158 0.00154 -0.00214 C2 1 0.464022 1.123108 0.365789 11.00000 0.01141 0.01306 = 0.01633 0.00111 -0.00137 -0.00352 C3 1 0.616315 0.981252 0.283055 11.00000 0.01747 0.02248 = 0.02616 -0.00365 0.00308 -0.00058 AFIX 137 H3A 2 0.671835 0.908600 0.281959 11.00000 -1.50000 H3B 2 0.694987 1.034711 0.261065 11.00000 -1.50000 H3C 2 0.503058 0.978763 0.258422 11.00000 -1.50000 AFIX 0 C4 1 0.764036 1.020415 0.397671 11.00000 0.01548 0.02078 = 0.03123 0.00305 -0.00302 -0.00175 AFIX 137 H4A 2 0.743229 1.028797 0.447011 11.00000 -1.50000 H4B 2 0.833219 1.082893 0.380811 11.00000 -1.50000 H4C 2 0.829702 0.952366 0.389263 11.00000 -1.50000 AFIX 0 C5 1 0.492414 1.182421 0.436052 11.00000 0.01795 0.02047 = 0.02171 -0.00511 0.00129 -0.00249 AFIX 137 H5A 2 0.401719 1.239242 0.441894 11.00000 -1.50000 H5B 2 0.610337 1.216237 0.436890 11.00000 -1.50000 H5C 2 0.482980 1.128955 0.473403 11.00000 -1.50000 AFIX 0 C6 1 0.485868 1.207402 0.307128 11.00000 0.01847 0.01709 = 0.02595 0.00551 0.00348 -0.00207 AFIX 137 H6A 2 0.452927 1.173254 0.263445 11.00000 -1.50000 H6B 2 0.609675 1.231701 0.305022 11.00000 -1.50000 H6C 2 0.408847 1.270667 0.315744 11.00000 -1.50000 AFIX 0 C7 1 0.151195 1.018064 0.504267 11.00000 0.01607 0.01842 = 0.01907 -0.00006 0.00028 -0.00458 AFIX 43 H7 2 0.173337 1.092123 0.491919 11.00000 -1.20000 AFIX 0 C8 1 0.087941 0.994929 0.570187 11.00000 0.02597 0.03066 = 0.01721 -0.00243 0.00293 -0.00626 AFIX 43 H8 2 0.065166 1.052246 0.601945 11.00000 -1.20000 AFIX 0 C9 1 0.058614 0.883493 0.588443 11.00000 0.02819 0.03938 = 0.01504 0.00485 0.00115 -0.01114 AFIX 43 H9 2 0.020666 0.865648 0.633513 11.00000 -1.20000 AFIX 0 C10 1 0.085301 0.800341 0.540499 11.00000 0.02193 0.02464 = 0.02283 0.01193 -0.00525 -0.00938 AFIX 43 H10 2 0.066040 0.725691 0.552158 11.00000 -1.20000 AFIX 0 C11 1 0.142001 0.830511 0.473877 11.00000 0.01265 0.01757 = 0.01892 0.00304 -0.00327 -0.00144 C12 1 0.121096 0.777221 0.354467 11.00000 0.01451 0.01429 = 0.01872 0.00062 -0.00132 0.00193 C13 1 0.174105 0.880828 0.329365 11.00000 0.01041 0.01306 = 0.01721 0.00037 0.00134 0.00200 C14 1 0.127106 0.904817 0.259673 11.00000 0.01367 0.01413 = 0.01841 -0.00119 0.00160 0.00151 AFIX 43 H14 2 0.156679 0.973817 0.240228 11.00000 -1.20000 AFIX 0 C15 1 0.036800 0.825627 0.220062 11.00000 0.01305 0.02045 = 0.01586 -0.00306 0.00194 0.00128 C16 1 -0.010241 0.721073 0.245872 11.00000 0.01345 0.01699 = 0.02496 -0.00750 0.00076 -0.00207 AFIX 43 H16 2 -0.068884 0.668924 0.217706 11.00000 -1.20000 AFIX 0 C17 1 0.032673 0.696477 0.314916 11.00000 0.01829 0.01041 = 0.02726 -0.00129 0.00058 -0.00209 AFIX 43 H17 2 0.002863 0.627443 0.334260 11.00000 -1.20000 HKLF 4 REM exp_188 in P212121 #19 REM R1 = 0.0251 for 3420 Fo > 4sig(Fo) and 0.0287 for all 3656 data REM 212 parameters refined using 0 restraints END ; _cod_data_source_file ol300950r_si_002.cif _cod_data_source_block nlt-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana Adding full bibliography for 1507718.cif. The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M P2(1)2(1)2(1) _cod_database_code 1507718 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags Br1 Br -0.02660(3) 0.861148(19) 0.124703(10) 0.02333(6) Uani 1 1 d . O1 O 0.47262(19) 0.93138(11) 0.39212(6) 0.0160(3) Uani 1 1 d . O2 O 0.28100(18) 1.07925(12) 0.36337(7) 0.0120(3) Uani 1 1 d . O3 O 0.1543(2) 0.74850(12) 0.42500(7) 0.0190(3) Uani 1 1 d . N1 N 0.1826(2) 0.93603(15) 0.45635(8) 0.0136(4) Uani 1 1 d . B1 B 0.2852(3) 0.96213(19) 0.38055(13) 0.0130(5) Uani 1 1 d . C1 C 0.5828(3) 1.01595(18) 0.35942(10) 0.0154(5) Uani 1 1 d . C2 C 0.4640(3) 1.12311(16) 0.36579(9) 0.0136(4) Uani 1 1 d . C3 C 0.6163(3) 0.9813(2) 0.28306(11) 0.0220(5) Uani 1 1 d . H3A H 0.6718 0.9086 0.2820 0.033 Uiso 1 1 calc R H3B H 0.6950 1.0347 0.2611 0.033 Uiso 1 1 calc R H3C H 0.5031 0.9788 0.2584 0.033 Uiso 1 1 calc R C4 C 0.7640(3) 1.0204(2) 0.39767(12) 0.0225(5) Uani 1 1 d . H4A H 0.7432 1.0288 0.4470 0.034 Uiso 1 1 calc R H4B H 0.8332 1.0829 0.3808 0.034 Uiso 1 1 calc R H4C H 0.8297 0.9524 0.3893 0.034 Uiso 1 1 calc R C5 C 0.4924(3) 1.18242(18) 0.43605(10) 0.0200(5) Uani 1 1 d . H5A H 0.4017 1.2392 0.4419 0.030 Uiso 1 1 calc R H5B H 0.6103 1.2162 0.4369 0.030 Uiso 1 1 calc R H5C H 0.4830 1.1290 0.4734 0.030 Uiso 1 1 calc R C6 C 0.4859(3) 1.20740(18) 0.30713(10) 0.0205(5) Uani 1 1 d . H6A H 0.4529 1.1733 0.2634 0.031 Uiso 1 1 calc R H6B H 0.6097 1.2317 0.3050 0.031 Uiso 1 1 calc R H6C H 0.4088 1.2707 0.3157 0.031 Uiso 1 1 calc R C7 C 0.1512(3) 1.0181(2) 0.50427(10) 0.0179(5) Uani 1 1 d . H7 H 0.1733 1.0921 0.4919 0.021 Uiso 1 1 calc R C8 C 0.0879(3) 0.9949(2) 0.57019(11) 0.0246(5) Uani 1 1 d . H8 H 0.0652 1.0522 0.6019 0.030 Uiso 1 1 calc R C9 C 0.0586(3) 0.8835(2) 0.58844(11) 0.0275(6) Uani 1 1 d . H9 H 0.0207 0.8656 0.6335 0.033 Uiso 1 1 calc R C10 C 0.0853(3) 0.8003(2) 0.54050(11) 0.0231(5) Uani 1 1 d . H10 H 0.0660 0.7257 0.5522 0.028 Uiso 1 1 calc R C11 C 0.1420(3) 0.83051(18) 0.47388(11) 0.0164(5) Uani 1 1 d . C12 C 0.1211(3) 0.77722(18) 0.35447(10) 0.0158(5) Uani 1 1 d . C13 C 0.1741(3) 0.88083(17) 0.32936(10) 0.0136(4) Uani 1 1 d . C14 C 0.1271(3) 0.90482(18) 0.25967(10) 0.0154(4) Uani 1 1 d . H14 H 0.1567 0.9738 0.2402 0.018 Uiso 1 1 calc R C15 C 0.0368(3) 0.82563(17) 0.22006(10) 0.0165(4) Uani 1 1 d . C16 C -0.0102(3) 0.72107(16) 0.24587(10) 0.0185(4) Uani 1 1 d . H16 H -0.0689 0.6689 0.2177 0.022 Uiso 1 1 calc R C17 C 0.0327(3) 0.69648(17) 0.31492(10) 0.0187(4) Uani 1 1 d . H17 H 0.0029 0.6274 0.3343 0.022 Uiso 1 1 calc R 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 Br1 0.02811(11) 0.02953(12) 0.01233(9) -0.00043(9) -0.00087(9) -0.01154(10) O1 0.0123(7) 0.0122(7) 0.0234(7) 0.0053(5) -0.0011(6) -0.0005(6) O2 0.0094(7) 0.0097(7) 0.0169(8) 0.0016(6) -0.0013(5) -0.0015(6) O3 0.0243(9) 0.0109(8) 0.0218(8) 0.0050(6) -0.0039(6) -0.0007(7) N1 0.0116(9) 0.0141(10) 0.0153(9) 0.0030(7) -0.0011(7) -0.0012(8) B1 0.0119(11) 0.0122(12) 0.0149(11) 0.0021(10) 0.0018(10) -0.0001(9) C1 0.0132(10) 0.0124(11) 0.0205(11) 0.0016(8) 0.0015(8) -0.0021(8) C2 0.0114(8) 0.0131(10) 0.0163(9) 0.0011(7) -0.0014(8) -0.0035(8) C3 0.0175(11) 0.0225(13) 0.0262(12) -0.0036(9) 0.0031(9) -0.0006(10) C4 0.0155(11) 0.0208(13) 0.0312(13) 0.0031(9) -0.0030(9) -0.0018(10) C5 0.0179(12) 0.0205(11) 0.0217(10) -0.0051(8) 0.0013(9) -0.0025(10) C6 0.0185(12) 0.0171(11) 0.0260(10) 0.0055(8) 0.0035(10) -0.0021(10) C7 0.0161(11) 0.0184(12) 0.0191(11) -0.0001(9) 0.0003(8) -0.0046(9) C8 0.0260(13) 0.0307(14) 0.0172(11) -0.0024(9) 0.0029(9) -0.0063(11) C9 0.0282(14) 0.0394(16) 0.0150(10) 0.0048(9) 0.0011(9) -0.0111(12) C10 0.0219(12) 0.0246(14) 0.0228(12) 0.0119(9) -0.0052(9) -0.0094(10) C11 0.0126(10) 0.0176(13) 0.0189(11) 0.0030(8) -0.0033(8) -0.0014(9) C12 0.0145(11) 0.0143(12) 0.0187(11) 0.0006(8) -0.0013(8) 0.0019(9) C13 0.0104(10) 0.0131(12) 0.0172(10) 0.0004(8) 0.0013(7) 0.0020(8) C14 0.0137(10) 0.0141(11) 0.0184(10) -0.0012(8) 0.0016(8) 0.0015(9) C15 0.0130(9) 0.0205(11) 0.0159(9) -0.0031(7) 0.0019(8) 0.0013(9) C16 0.0135(11) 0.0170(10) 0.0250(10) -0.0075(8) 0.0008(9) -0.0021(9) C17 0.0183(10) 0.0104(10) 0.0273(11) -0.0013(8) 0.0006(10) -0.0021(10) 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' B B 0.0013 0.0007 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 B1 107.20(15) B1 O2 C2 108.92(14) C11 O3 C12 118.01(16) C11 N1 C7 118.16(17) C11 N1 B1 119.76(16) C7 N1 B1 121.87(17) O2 B1 O1 107.60(17) O2 B1 C13 116.05(18) O1 B1 C13 115.35(17) O2 B1 N1 111.80(16) O1 B1 N1 104.77(16) C13 B1 N1 100.60(15) O1 C1 C4 108.21(17) O1 C1 C3 108.28(17) C4 C1 C3 108.83(18) O1 C1 C2 102.98(15) C4 C1 C2 115.35(18) C3 C1 C2 112.76(16) O2 C2 C6 108.41(16) O2 C2 C5 108.82(15) C6 C2 C5 109.02(16) O2 C2 C1 103.04(15) C6 C2 C1 115.39(16) C5 C2 C1 111.82(16) C1 C3 H3A 109.5 C1 C3 H3B 109.5 H3A C3 H3B 109.5 C1 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C1 C4 H4A 109.5 C1 C4 H4B 109.5 H4A C4 H4B 109.5 C1 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 C2 C5 H5A 109.5 C2 C5 H5B 109.5 H5A C5 H5B 109.5 C2 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C2 C6 H6A 109.5 C2 C6 H6B 109.5 H6A C6 H6B 109.5 C2 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 N1 C7 C8 122.0(2) N1 C7 H7 119.0 C8 C7 H7 119.0 C7 C8 C9 118.4(2) C7 C8 H8 120.8 C9 C8 H8 120.8 C10 C9 C8 120.3(2) C10 C9 H9 119.8 C8 C9 H9 119.8 C9 C10 C11 118.0(2) C9 C10 H10 121.0 C11 C10 H10 121.0 N1 C11 O3 119.54(18) N1 C11 C10 122.8(2) O3 C11 C10 117.6(2) C13 C12 C17 124.47(18) C13 C12 O3 119.93(18) C17 C12 O3 115.60(18) C12 C13 C14 116.15(19) C12 C13 B1 118.37(17) C14 C13 B1 125.47(19) C15 C14 C13 119.86(19) C15 C14 H14 120.1 C13 C14 H14 120.1 C14 C15 C16 122.85(19) C14 C15 Br1 118.91(16) C16 C15 Br1 118.24(15) C17 C16 C15 118.11(18) C17 C16 H16 120.9 C15 C16 H16 120.9 C16 C17 C12 118.52(19) C16 C17 H17 120.7 C12 C17 H17 120.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C15 1.9277(19) O1 C1 1.440(2) O1 B1 1.449(3) O2 B1 1.437(3) O2 C2 1.450(2) O3 C11 1.356(2) O3 C12 1.412(2) N1 C11 1.338(3) N1 C7 1.361(3) N1 B1 1.663(3) B1 C13 1.604(3) C1 C4 1.526(3) C1 C3 1.536(3) C1 C2 1.556(3) C2 C6 1.515(3) C2 C5 1.532(3) C3 H3A 0.9600 C3 H3B 0.9600 C3 H3C 0.9600 C4 H4A 0.9600 C4 H4B 0.9600 C4 H4C 0.9600 C5 H5A 0.9600 C5 H5B 0.9600 C5 H5C 0.9600 C6 H6A 0.9600 C6 H6B 0.9600 C6 H6C 0.9600 C7 C8 1.371(3) C7 H7 0.9300 C8 C9 1.393(3) C8 H8 0.9300 C9 C10 1.365(3) C9 H9 0.9300 C10 C11 1.387(3) C10 H10 0.9300 C12 C13 1.384(3) C12 C17 1.388(3) C13 C14 1.405(3) C14 C15 1.383(3) C14 H14 0.9300 C15 C16 1.387(3) C16 C17 1.388(3) C16 H16 0.9300 C17 H17 0.9300