#------------------------------------------------------------------------------ #$Date: 2020-02-28 04:12:04 +0200 (Fri, 28 Feb 2020) $ #$Revision: 248515 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557394.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_1557394 loop_ _publ_author_name 'Liu, Lei' 'Lee, Wes' 'Yuan, Mingbin' 'Acha, Chris' 'Geherty, Michael B.' 'Williams, Brandon' 'Gutierrez, Osvaldo' _publ_section_title ; Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC00467G _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C16 H14 O2' _chemical_formula_sum 'C16 H14 O2' _chemical_formula_weight 238.27 _chemical_name_systematic 3-([1,1'-biphenyl]-4-yl)dihydrofuran-2(3H)-one _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXL-2015 & ZCIF' _audit_update_record ; 2019-10-02 deposited with the CCDC. 2020-02-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.1686(18) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.2309(7) _cell_length_b 7.4169(8) _cell_length_c 13.0054(15) _cell_measurement_reflns_used 3426 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.7 _cell_measurement_theta_min 3.1 _cell_volume 601.03(12) _computing_cell_refinement 'Apex2, Saint' _computing_data_collection 'Apex2 (Bruker, 2010)' _computing_data_reduction 'Apex2, Saint' _computing_molecular_graphics 'Olex2 (Dolomanov, 2009)' _computing_publication_material 'Apex2, SHELXL-2015, Platon (Spek, 2015)' _computing_structure_refinement 'ShelXL-2015 (Sheldrick, 2015c)' _computing_structure_solution 'ShelXT-2014 (Sheldrick, 2015a)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker Smart Apex II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 -0.0302051 _diffrn_orient_matrix_UB_12 -0.1321729 _diffrn_orient_matrix_UB_13 -0.0045866 _diffrn_orient_matrix_UB_21 0.0008765 _diffrn_orient_matrix_UB_22 -0.0082530 _diffrn_orient_matrix_UB_23 0.0767455 _diffrn_orient_matrix_UB_31 -0.1576189 _diffrn_orient_matrix_UB_32 0.0252972 _diffrn_orient_matrix_UB_33 0.0010755 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8759 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.000 _diffrn_reflns_theta_min 1.566 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Krause et al, 2015)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 252 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.025 _refine_diff_density_max 0.273 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details ; Flack x determined using 1312 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.1(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 3504 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0364 _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^)+(0.0090P)^2^+0.2443P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.0725 _reflns_Friedel_coverage 0.858 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.991 _reflns_number_gt 3114 _reflns_number_total 3504 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00467g2.cif _cod_data_source_block UM3320 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1557394 _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 0.963 _shelx_estimated_absorpt_t_max 0.998 _shelx_res_file ; TITL a in P2(1) a.res created by SHELXL-2017/1 at 19:27:38 on 07-Sep-2019 CELL 0.71073 6.23090 7.41690 13.00540 90.0000 90.1686 90.0000 ZERR 2.00 0.00070 0.00080 0.00150 0.0000 0.0018 0.0000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H O UNIT 32 28 4 OMIT -2.00 60 L.S. 10 ACTA BOND $H CONF FMAP 2 MPLA 6 C13 > C18 C10 MPLA 6 C7 > C12 C13 C6 MPLA 5 O1 > C4 C6 C5 PLAN 20 SIZE 0.025 0.20 0.44 TEMP -123.140 WGHT 0.009000 0.244300 FVAR 0.37704 O1 3 0.402495 0.704377 0.098597 11.00000 0.03724 0.04914 = 0.03918 0.01427 0.00069 0.01322 C2 1 0.556840 0.608645 0.093694 11.00000 0.02989 0.03717 = 0.01813 0.00295 -0.00255 -0.00031 O3 3 0.732040 0.656171 0.038792 11.00000 0.03514 0.03703 = 0.03049 0.00943 0.00479 -0.00124 C4 1 0.891017 0.511855 0.040363 11.00000 0.03072 0.04063 = 0.02899 -0.00212 0.00785 -0.00324 H4A 2 0.874434 0.448655 -0.025302 11.00000 0.04405 H4B 2 1.035887 0.564485 0.044411 11.00000 0.03543 C5 1 0.832742 0.396288 0.132353 11.00000 0.02722 0.03359 = 0.02733 -0.00056 0.00508 0.00548 H5A 2 0.903703 0.436794 0.194384 11.00000 0.02896 H5B 2 0.874517 0.260207 0.122963 11.00000 0.03779 C6 1 0.589540 0.422498 0.141360 11.00000 0.02572 0.02756 = 0.01830 -0.00215 0.00172 -0.00128 H6 2 0.516302 0.345014 0.093145 11.00000 0.02726 C7 1 0.494230 0.406802 0.247622 11.00000 0.02346 0.01934 = 0.01947 0.00048 0.00146 0.00157 C8 1 0.310906 0.304462 0.265060 11.00000 0.02281 0.02566 = 0.02095 -0.00267 -0.00260 -0.00122 H8 2 0.246614 0.233985 0.206689 11.00000 0.02716 C9 1 0.216032 0.296782 0.361810 11.00000 0.02009 0.02482 = 0.02460 -0.00066 0.00017 -0.00450 H9 2 0.088649 0.230646 0.371643 11.00000 0.03200 C10 1 0.302259 0.391550 0.445409 11.00000 0.02108 0.01721 = 0.01850 0.00107 0.00040 0.00075 C11 1 0.491380 0.488325 0.427866 11.00000 0.02841 0.02645 = 0.02117 -0.00409 0.00009 -0.00947 H11 2 0.558217 0.551370 0.483949 11.00000 0.03545 C12 1 0.585351 0.496131 0.331298 11.00000 0.02820 0.02607 = 0.02386 -0.00324 0.00369 -0.00843 H12 2 0.713259 0.564718 0.322027 11.00000 0.03477 C13 1 0.200765 0.388204 0.549250 11.00000 0.02326 0.01638 = 0.01984 0.00198 0.00155 0.00110 C14 1 -0.004397 0.314983 0.564472 11.00000 0.02404 0.02459 = 0.02685 -0.00028 0.00170 -0.00048 H14 2 -0.086002 0.272132 0.503825 11.00000 0.02647 C15 1 -0.093504 0.305190 0.662083 11.00000 0.02664 0.02762 = 0.03305 0.00268 0.00790 -0.00016 H15 2 -0.236134 0.257882 0.670810 11.00000 0.03850 C16 1 0.018146 0.368973 0.746857 11.00000 0.03814 0.02810 = 0.02427 0.00108 0.00985 0.00391 H16 2 -0.043595 0.357972 0.814345 11.00000 0.02504 C17 1 0.219823 0.444086 0.733159 11.00000 0.03741 0.03055 = 0.02303 -0.00348 0.00037 0.00035 H17 2 0.305054 0.478185 0.793621 11.00000 0.03343 C18 1 0.309812 0.453617 0.635773 11.00000 0.02780 0.02721 = 0.02320 -0.00176 0.00177 -0.00346 H18 2 0.454671 0.492297 0.629136 11.00000 0.03539 HKLF 4 REM a in P2(1) REM R1 = 0.0364 for 3114 Fo > 4sig(Fo) and 0.0424 for all 3504 data REM 219 parameters refined using 1 restraints END WGHT 0.0630 0.0084 REM Highest difference peak 0.273, deepest hole -0.160, 1-sigma level 0.036 Q1 1 0.2609 0.3825 0.5004 11.00000 0.05 0.27 Q2 1 0.5568 0.4159 0.1964 11.00000 0.05 0.27 Q3 1 0.7123 0.4139 0.1429 11.00000 0.05 0.25 Q4 1 0.4106 0.4248 0.4431 11.00000 0.05 0.23 Q5 1 0.0928 0.3644 0.5621 11.00000 0.05 0.22 Q6 1 -0.0291 0.3236 0.6179 11.00000 0.05 0.21 Q7 1 0.4311 0.3203 0.2637 11.00000 0.05 0.21 Q8 1 0.5458 0.4265 0.2989 11.00000 0.05 0.21 Q9 1 0.2460 0.4412 0.6815 11.00000 0.05 0.21 Q10 1 0.2964 0.2885 0.3223 11.00000 0.05 0.20 Q11 1 0.2385 0.4178 0.5984 11.00000 0.05 0.19 Q12 1 0.2721 0.3404 0.4022 11.00000 0.05 0.19 Q13 1 0.4888 0.5004 0.3666 11.00000 0.05 0.18 Q14 1 -0.0868 0.3364 0.6043 11.00000 0.05 0.18 Q15 1 0.1394 0.3839 0.7381 11.00000 0.05 0.18 Q16 1 0.5396 0.4820 0.3762 11.00000 0.05 0.18 Q17 1 0.0945 0.4549 0.7388 11.00000 0.05 0.17 Q18 1 0.3710 0.3997 0.2551 11.00000 0.05 0.17 Q19 1 -0.0235 0.3415 0.6979 11.00000 0.05 0.16 Q20 1 0.8638 0.4389 0.0818 11.00000 0.05 0.14 ; _shelx_res_checksum 22757 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 O1 O 0.4025(3) 0.7044(3) 0.09860(12) 0.0419(4) Uani 1 1 d . . . . . C2 C 0.5568(3) 0.6086(3) 0.09369(14) 0.0284(4) Uani 1 1 d . . . . . O3 O 0.7320(2) 0.6562(2) 0.03879(11) 0.0342(4) Uani 1 1 d . . . . . C4 C 0.8910(4) 0.5119(3) 0.04036(18) 0.0334(5) Uani 1 1 d . . . . . H4A H 0.874(4) 0.449(4) -0.025(2) 0.044(7) Uiso 1 1 d . . . . . H4B H 1.036(4) 0.564(4) 0.0444(18) 0.035(7) Uiso 1 1 d . . . . . C5 C 0.8327(3) 0.3963(3) 0.13235(16) 0.0294(4) Uani 1 1 d . . . . . H5A H 0.904(3) 0.437(3) 0.1944(18) 0.029(6) Uiso 1 1 d . . . . . H5B H 0.875(4) 0.260(4) 0.1230(18) 0.038(7) Uiso 1 1 d . . . . . C6 C 0.5895(3) 0.4225(3) 0.14136(14) 0.0239(4) Uani 1 1 d . . . . . H6 H 0.516(3) 0.345(3) 0.0931(17) 0.027(6) Uiso 1 1 d . . . . . C7 C 0.4942(3) 0.4068(2) 0.24762(13) 0.0208(4) Uani 1 1 d . . . . . C8 C 0.3109(3) 0.3045(3) 0.26506(14) 0.0231(4) Uani 1 1 d . . . . . H8 H 0.247(4) 0.234(3) 0.2067(17) 0.027(6) Uiso 1 1 d . . . . . C9 C 0.2160(3) 0.2968(3) 0.36181(15) 0.0232(4) Uani 1 1 d . . . . . H9 H 0.089(4) 0.231(3) 0.3716(17) 0.032(6) Uiso 1 1 d . . . . . C10 C 0.3023(3) 0.3915(2) 0.44541(13) 0.0189(3) Uani 1 1 d . . . . . C11 C 0.4914(3) 0.4883(3) 0.42787(15) 0.0253(4) Uani 1 1 d . . . . . H11 H 0.558(4) 0.551(4) 0.4839(19) 0.035(7) Uiso 1 1 d . . . . . C12 C 0.5854(3) 0.4961(3) 0.33130(16) 0.0260(4) Uani 1 1 d . . . . . H12 H 0.713(4) 0.565(3) 0.3220(18) 0.035(7) Uiso 1 1 d . . . . . C13 C 0.2008(3) 0.3882(2) 0.54925(14) 0.0198(3) Uani 1 1 d . . . . . C14 C -0.0044(3) 0.3150(3) 0.56447(16) 0.0252(4) Uani 1 1 d . . . . . H14 H -0.086(3) 0.272(3) 0.5038(17) 0.026(6) Uiso 1 1 d . . . . . C15 C -0.0935(3) 0.3052(3) 0.66208(16) 0.0291(4) Uani 1 1 d . . . . . H15 H -0.236(4) 0.258(4) 0.6708(18) 0.039(7) Uiso 1 1 d . . . . . C16 C 0.0181(4) 0.3690(3) 0.74686(16) 0.0302(4) Uani 1 1 d . . . . . H16 H -0.044(3) 0.358(3) 0.8143(17) 0.025(6) Uiso 1 1 d . . . . . C17 C 0.2198(4) 0.4441(3) 0.73316(16) 0.0303(4) Uani 1 1 d . . . . . H17 H 0.305(4) 0.478(3) 0.7936(19) 0.033(6) Uiso 1 1 d . . . . . C18 C 0.3098(3) 0.4536(3) 0.63577(15) 0.0261(4) Uani 1 1 d . . . . . H18 H 0.455(4) 0.492(4) 0.6291(19) 0.035(7) Uiso 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 O1 0.0372(9) 0.0491(10) 0.0392(9) 0.0143(8) 0.0007(7) 0.0132(8) C2 0.0299(9) 0.0372(11) 0.0181(8) 0.0030(8) -0.0026(7) -0.0003(8) O3 0.0351(8) 0.0370(9) 0.0305(7) 0.0094(7) 0.0048(6) -0.0012(7) C4 0.0307(11) 0.0406(13) 0.0290(11) -0.0021(10) 0.0078(8) -0.0032(10) C5 0.0272(9) 0.0336(11) 0.0273(10) -0.0006(9) 0.0051(7) 0.0055(8) C6 0.0257(9) 0.0276(10) 0.0183(8) -0.0022(8) 0.0017(7) -0.0013(8) C7 0.0235(8) 0.0193(9) 0.0195(8) 0.0005(7) 0.0015(6) 0.0016(7) C8 0.0228(8) 0.0257(9) 0.0210(9) -0.0027(8) -0.0026(7) -0.0012(8) C9 0.0201(8) 0.0248(9) 0.0246(9) -0.0007(8) 0.0002(7) -0.0045(7) C10 0.0211(8) 0.0172(8) 0.0185(8) 0.0011(7) 0.0004(6) 0.0008(7) C11 0.0284(10) 0.0264(10) 0.0212(9) -0.0041(8) 0.0001(7) -0.0095(8) C12 0.0282(10) 0.0261(10) 0.0239(10) -0.0032(8) 0.0037(8) -0.0084(8) C13 0.0233(8) 0.0164(8) 0.0198(8) 0.0020(7) 0.0015(6) 0.0011(7) C14 0.0240(9) 0.0246(10) 0.0268(9) -0.0003(8) 0.0017(7) -0.0005(8) C15 0.0266(10) 0.0276(10) 0.0331(11) 0.0027(9) 0.0079(8) -0.0002(9) C16 0.0381(11) 0.0281(11) 0.0243(10) 0.0011(8) 0.0098(8) 0.0039(9) C17 0.0374(11) 0.0306(11) 0.0230(10) -0.0035(8) 0.0004(8) 0.0003(9) C18 0.0278(10) 0.0272(10) 0.0232(10) -0.0018(8) 0.0018(7) -0.0035(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 121.5(2) . . ? O1 C2 C6 128.4(2) . . ? O3 C2 C6 110.06(17) . . ? C2 O3 C4 110.51(16) . . ? O3 C4 C5 105.17(16) . . ? O3 C4 H4A 105.6(16) . . ? C5 C4 H4A 113.1(16) . . ? O3 C4 H4B 109.4(15) . . ? C5 C4 H4B 113.8(14) . . ? H4A C4 H4B 109(2) . . ? C4 C5 C6 103.16(17) . . ? C4 C5 H5A 111.9(14) . . ? C6 C5 H5A 110.3(13) . . ? C4 C5 H5B 113.1(13) . . ? C6 C5 H5B 112.1(13) . . ? H5A C5 H5B 106(2) . . ? C7 C6 C2 112.88(16) . . ? C7 C6 C5 116.85(16) . . ? C2 C6 C5 102.38(17) . . ? C7 C6 H6 111.3(13) . . ? C2 C6 H6 102.3(14) . . ? C5 C6 H6 109.9(13) . . ? C8 C7 C12 117.72(17) . . ? C8 C7 C6 121.11(16) . . ? C12 C7 C6 121.17(16) . . ? C7 C8 C9 121.37(18) . . ? C7 C8 H8 119.1(13) . . ? C9 C8 H8 119.5(13) . . ? C8 C9 C10 121.19(18) . . ? C8 C9 H9 120.3(14) . . ? C10 C9 H9 118.5(14) . . ? C11 C10 C9 116.89(16) . . ? C11 C10 C13 121.01(16) . . ? C9 C10 C13 122.09(15) . . ? C12 C11 C10 121.77(18) . . ? C12 C11 H11 118.9(15) . . ? C10 C11 H11 119.3(15) . . ? C11 C12 C7 120.97(18) . . ? C11 C12 H12 119.4(15) . . ? C7 C12 H12 119.6(14) . . ? C18 C13 C14 117.45(18) . . ? C18 C13 C10 121.03(16) . . ? C14 C13 C10 121.49(16) . . ? C15 C14 C13 121.05(19) . . ? C15 C14 H14 120.4(13) . . ? C13 C14 H14 118.6(13) . . ? C16 C15 C14 120.56(19) . . ? C16 C15 H15 119.5(15) . . ? C14 C15 H15 119.9(14) . . ? C15 C16 C17 119.22(19) . . ? C15 C16 H16 119.7(13) . . ? C17 C16 H16 121.1(13) . . ? C16 C17 C18 120.4(2) . . ? C16 C17 H17 119.3(14) . . ? C18 C17 H17 119.9(14) . . ? C17 C18 C13 121.29(19) . . ? C17 C18 H18 118.9(15) . . ? C13 C18 H18 119.3(15) . . ? 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 O1 C2 1.197(3) . ? C2 O3 1.353(2) . ? C2 C6 1.527(3) . ? O3 C4 1.459(3) . ? C4 C5 1.517(3) . ? C4 H4A 0.98(3) . ? C4 H4B 0.98(3) . ? C5 C6 1.533(3) . ? C5 H5A 0.97(2) . ? C5 H5B 1.05(3) . ? C6 C7 1.510(2) . ? C6 H6 0.96(2) . ? C7 C8 1.391(3) . ? C7 C12 1.394(3) . ? C8 C9 1.393(3) . ? C8 H8 1.00(2) . ? C9 C10 1.400(3) . ? C9 H9 0.94(2) . ? C10 C11 1.399(3) . ? C10 C13 1.493(2) . ? C11 C12 1.388(3) . ? C11 H11 0.96(3) . ? C12 H12 0.95(2) . ? C13 C18 1.400(3) . ? C13 C14 1.403(3) . ? C14 C15 1.389(3) . ? C14 H14 0.99(2) . ? C15 C16 1.385(3) . ? C15 H15 0.96(3) . ? C16 C17 1.387(3) . ? C16 H16 0.96(2) . ? C17 C18 1.388(3) . ? C17 H17 0.98(2) . ? C18 H18 0.95(2) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 O3 C4 -176.6(2) . . . . ? C6 C2 O3 C4 1.9(2) . . . . ? C2 O3 C4 C5 -19.8(2) . . . . ? O3 C4 C5 C6 28.8(2) . . . . ? O1 C2 C6 C7 -38.8(3) . . . . ? O3 C2 C6 C7 142.84(16) . . . . ? O1 C2 C6 C5 -165.3(2) . . . . ? O3 C2 C6 C5 16.4(2) . . . . ? C4 C5 C6 C7 -150.78(18) . . . . ? C4 C5 C6 C2 -26.9(2) . . . . ? C2 C6 C7 C8 108.5(2) . . . . ? C5 C6 C7 C8 -133.2(2) . . . . ? C2 C6 C7 C12 -70.7(2) . . . . ? C5 C6 C7 C12 47.6(3) . . . . ? C12 C7 C8 C9 2.5(3) . . . . ? C6 C7 C8 C9 -176.72(18) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 -2.2(3) . . . . ? C8 C9 C10 C13 178.75(18) . . . . ? C9 C10 C11 C12 2.4(3) . . . . ? C13 C10 C11 C12 -178.57(19) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C8 C7 C12 C11 -2.3(3) . . . . ? C6 C7 C12 C11 176.9(2) . . . . ? C11 C10 C13 C18 -11.6(3) . . . . ? C9 C10 C13 C18 167.4(2) . . . . ? C11 C10 C13 C14 170.3(2) . . . . ? C9 C10 C13 C14 -10.7(3) . . . . ? C18 C13 C14 C15 -1.1(3) . . . . ? C10 C13 C14 C15 177.10(18) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C16 C17 C18 C13 0.0(3) . . . . ? C14 C13 C18 C17 0.9(3) . . . . ? C10 C13 C18 C17 -177.32(18) . . . . ?