#------------------------------------------------------------------------------ #$Date: 2026-05-29 00:32:05 +0100 (Fri, 29 May 2026) $ #$Revision: 306116 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577317.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_1577317 loop_ _publ_author_name 'Teschers, Charlotte S.' 'Barra, Cyriac' 'Scher\"ubl, Maximilian' 'Zuber, Julian' 'Marek, Ilan' _publ_section_title ; Diastereoselective Synthesis of Spiro[2,n]alkanes via Intramolecular Carbolithiation ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03169B _journal_year 2026 _chemical_formula_sum 'C15 H18 O3' _chemical_formula_weight 246.29 _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method ;FinalCif V144 by Daniel Kratzert, Freiburg 2025, https://dkratzert.de/finalcif.html ; _audit_update_record ; 2026-04-15 deposited with the CCDC. 2026-05-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.101(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7981(8) _cell_length_b 7.4662(5) _cell_length_c 16.4344(12) _cell_measurement_reflns_used 9951 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.3215 _cell_measurement_theta_min 2.4825 _cell_volume 1323.01(16) _computing_cell_refinement 'SAINT V8.40B' _computing_data_collection 'Bruker BIS V6.2.16/2021-10-23 and APEX4 2021.10-0' _computing_data_reduction 'SAINT V8.40B' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2004)' _computing_structure_refinement 'SHELXL (Sheldrick, 2015), SHELXLE (Huebschle, 2011)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector CPAD _diffrn_detector_area_resol_mean 16 _diffrn_detector_type 'Bruker PHOTON III' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device 'three-angle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\w and \f scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_radiation_monochromator 'Helios optic' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 69964 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.504 _diffrn_reflns_theta_min 2.482 _diffrn_source 'TXS rotating anode' _diffrn_source_current 50.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7051 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2016/2 (Bruker, 2016)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.237 _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.098 _exptl_crystal_size_mid 0.089 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.280 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2726 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0351 _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^)+(0.0493P)^2^+0.4493P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.0971 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2331 _reflns_number_total 2726 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03169b2.cif _cod_data_source_block TesCh2 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1577317 _shelx_shelxl_version_number 2019/3 _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. ; _diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream' _shelx_res_file ; TITL TesCh2_a.res in P2(1)/n TesCh2.res created by SHELXL-2019/3 at 15:31:08 on 08-Jul-2025 CELL 0.71073 10.7981 7.4662 16.4344 90.0000 93.1010 90.0000 ZERR 4.00 0.0008 0.0005 0.0012 0.0000 0.0030 0.0000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H O UNIT 60 72 12 OMIT 1 0 3 !affected by beamstop LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -173.150 ACTA L.S. 4 FMAP 2 PLAN -20 0 0.00 HTAB BOND $H CONF WGHT 0.049300 0.449300 FVAR 0.73904 O1 3 0.921861 0.325529 0.373633 11.00000 0.01560 0.02122 = 0.04534 0.00402 0.00038 0.00025 O2 3 0.591920 0.172861 0.488817 11.00000 0.02175 0.01898 = 0.01443 0.00269 -0.00329 -0.00390 O3 3 0.452799 0.059939 0.397212 11.00000 0.02463 0.01931 = 0.01697 0.00396 -0.00493 -0.00788 AFIX 148 H3A 2 0.439959 -0.015234 0.437852 11.00000 -1.50000 AFIX 0 C1 1 1.028725 0.223899 0.398220 11.00000 0.01761 0.03175 = 0.05580 0.00182 -0.00163 0.00390 AFIX 137 H1A 2 1.025240 0.191532 0.455841 11.00000 -1.50000 H1B 2 1.103335 0.295330 0.390548 11.00000 -1.50000 H1C 2 1.031282 0.114761 0.365225 11.00000 -1.50000 AFIX 0 C2 1 0.811847 0.224592 0.379971 11.00000 0.01700 0.01757 = 0.02139 -0.00047 0.00079 0.00011 AFIX 23 H2A 2 0.796081 0.202413 0.437893 11.00000 -1.20000 H2B 2 0.818974 0.107777 0.352107 11.00000 -1.20000 AFIX 0 C3 1 0.708497 0.333354 0.340007 11.00000 0.01644 0.01688 = 0.01620 0.00054 0.00145 -0.00113 AFIX 13 H3 2 0.722813 0.365497 0.282197 11.00000 -1.20000 AFIX 0 C4 1 0.570636 0.304381 0.355950 11.00000 0.01611 0.01495 = 0.01397 0.00034 0.00043 0.00055 C5 1 0.640328 0.473689 0.383718 11.00000 0.01678 0.01505 = 0.01570 0.00060 0.00055 -0.00117 C6 1 0.540513 0.174319 0.420190 11.00000 0.01481 0.01380 = 0.01619 -0.00097 0.00026 0.00137 C7 1 0.480017 0.311207 0.283190 11.00000 0.01845 0.01504 = 0.01405 0.00268 0.00008 -0.00179 C8 1 0.502177 0.213987 0.213138 11.00000 0.01977 0.01766 = 0.01874 -0.00013 0.00022 0.00094 AFIX 43 H8 2 0.576898 0.147655 0.210305 11.00000 -1.20000 AFIX 0 C9 1 0.415722 0.213348 0.147346 11.00000 0.02746 0.02122 = 0.01596 -0.00205 -0.00035 -0.00186 AFIX 43 H9 2 0.431530 0.146535 0.099818 11.00000 -1.20000 AFIX 0 C10 1 0.306534 0.309864 0.150859 11.00000 0.02298 0.02314 = 0.01811 0.00315 -0.00597 -0.00300 AFIX 43 H10 2 0.247635 0.309421 0.105774 11.00000 -1.20000 AFIX 0 C11 1 0.283324 0.407407 0.220526 11.00000 0.01964 0.02341 = 0.02309 0.00292 -0.00190 0.00356 AFIX 43 H11 2 0.208594 0.473817 0.223106 11.00000 -1.20000 AFIX 0 C12 1 0.369860 0.407462 0.286438 11.00000 0.02142 0.01945 = 0.01597 0.00041 0.00116 0.00143 AFIX 43 H12 2 0.353674 0.473711 0.334059 11.00000 -1.20000 AFIX 0 C13 1 0.618992 0.664902 0.353352 11.00000 0.02315 0.01618 = 0.02057 0.00177 0.00220 -0.00071 AFIX 23 H13A 2 0.531800 0.705560 0.354147 11.00000 -1.20000 H13B 2 0.654200 0.690290 0.300177 11.00000 -1.20000 AFIX 0 C14 1 0.702324 0.726208 0.428282 11.00000 0.02518 0.01690 = 0.02498 -0.00240 0.00182 -0.00231 AFIX 23 H14A 2 0.789897 0.747218 0.416014 11.00000 -1.20000 H14B 2 0.668451 0.829234 0.457807 11.00000 -1.20000 AFIX 0 C15 1 0.679484 0.542458 0.469033 11.00000 0.02067 0.01763 = 0.01754 -0.00183 0.00008 -0.00162 AFIX 23 H15A 2 0.755333 0.485258 0.493573 11.00000 -1.20000 H15B 2 0.611978 0.543228 0.507464 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM TesCh2_a.res in P2(1)/n REM wR2 = 0.0971, GooF = S = 1.065, Restrained GooF = 1.065 for all data REM R1 = 0.0351 for 2331 Fo > 4sig(Fo) and 0.0448 for all 2726 data REM 166 parameters refined using 0 restraints END WGHT 0.0493 0.4493 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y, -z+1 HTAB O3 O2_$1 HTAB C2 O2 REM Highest difference peak 0.280, deepest hole -0.189, 1-sigma level 0.041 Q1 1 0.6590 0.4863 0.4255 11.00000 0.05 0.28 Q2 1 0.5608 0.2456 0.3860 11.00000 0.05 0.28 Q3 1 0.5251 0.3090 0.3207 11.00000 0.05 0.27 Q4 1 0.7579 0.2816 0.3608 11.00000 0.05 0.27 Q5 1 0.6240 0.5540 0.3598 11.00000 0.05 0.26 Q6 1 0.5850 0.4019 0.3827 11.00000 0.05 0.26 Q7 1 0.7013 0.4295 0.3651 11.00000 0.05 0.23 Q8 1 0.6627 0.7181 0.3862 11.00000 0.05 0.22 Q9 1 0.5049 0.2850 0.2498 11.00000 0.05 0.22 Q10 1 0.6969 0.6335 0.4553 11.00000 0.05 0.21 Q11 1 0.6405 0.2831 0.3407 11.00000 0.05 0.20 Q12 1 0.2912 0.3268 0.1946 11.00000 0.05 0.19 Q13 1 0.4555 0.2300 0.1785 11.00000 0.05 0.18 Q14 1 0.4420 0.3779 0.2813 11.00000 0.05 0.18 Q15 1 0.3177 0.3721 0.2560 11.00000 0.05 0.17 Q16 1 0.3453 0.4314 0.2464 11.00000 0.05 0.16 Q17 1 0.3826 0.3047 0.1540 11.00000 0.05 0.16 Q18 1 0.8005 0.1781 0.4208 11.00000 0.05 0.15 Q19 1 0.7798 0.6858 0.4050 11.00000 0.05 0.15 Q20 1 0.5641 0.1901 0.4600 11.00000 0.05 0.15 ; _shelx_res_checksum 60929 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 O1 O 0.92186(8) 0.32553(13) 0.37363(6) 0.0274(2) Uani 1 1 d . . . . . O2 O 0.59192(8) 0.17286(11) 0.48882(5) 0.0185(2) Uani 1 1 d . . . . . O3 O 0.45280(8) 0.05994(12) 0.39721(5) 0.0205(2) Uani 1 1 d . . . . . H3A H 0.4400(10) -0.015(2) 0.4379(9) 0.031 Uiso 1 1 calc R U . . . C1 C 1.02872(12) 0.2239(2) 0.39822(11) 0.0352(4) Uani 1 1 d . . . . . H1A H 1.025240 0.191532 0.455841 0.053 Uiso 1 1 calc R U . . . H1B H 1.103335 0.295330 0.390548 0.053 Uiso 1 1 calc R U . . . H1C H 1.031282 0.114761 0.365225 0.053 Uiso 1 1 calc R U . . . C2 C 0.81185(11) 0.22459(16) 0.37997(7) 0.0187(3) Uani 1 1 d . . . . . H2A H 0.796081 0.202413 0.437893 0.022 Uiso 1 1 calc R U . . . H2B H 0.818974 0.107777 0.352107 0.022 Uiso 1 1 calc R U . . . C3 C 0.70850(10) 0.33335(16) 0.34001(7) 0.0165(2) Uani 1 1 d . . . . . H3 H 0.722813 0.365497 0.282197 0.020 Uiso 1 1 calc R U . . . C4 C 0.57064(10) 0.30438(15) 0.35595(7) 0.0150(2) Uani 1 1 d . . . . . C5 C 0.64033(10) 0.47369(16) 0.38372(7) 0.0159(2) Uani 1 1 d . . . . . C6 C 0.54051(10) 0.17432(15) 0.42019(7) 0.0150(2) Uani 1 1 d . . . . . C7 C 0.48002(11) 0.31121(15) 0.28319(7) 0.0159(2) Uani 1 1 d . . . . . C8 C 0.50218(11) 0.21399(16) 0.21314(7) 0.0188(3) Uani 1 1 d . . . . . H8 H 0.576898 0.147655 0.210305 0.023 Uiso 1 1 calc R U . . . C9 C 0.41572(12) 0.21335(17) 0.14735(7) 0.0216(3) Uani 1 1 d . . . . . H9 H 0.431530 0.146535 0.099818 0.026 Uiso 1 1 calc R U . . . C10 C 0.30653(12) 0.30986(17) 0.15086(7) 0.0217(3) Uani 1 1 d . . . . . H10 H 0.247635 0.309421 0.105774 0.026 Uiso 1 1 calc R U . . . C11 C 0.28332(11) 0.40741(18) 0.22053(8) 0.0222(3) Uani 1 1 d . . . . . H11 H 0.208594 0.473817 0.223106 0.027 Uiso 1 1 calc R U . . . C12 C 0.36986(11) 0.40746(17) 0.28644(7) 0.0189(3) Uani 1 1 d . . . . . H12 H 0.353674 0.473711 0.334059 0.023 Uiso 1 1 calc R U . . . C13 C 0.61899(11) 0.66490(16) 0.35335(8) 0.0199(3) Uani 1 1 d . . . . . H13A H 0.531800 0.705560 0.354147 0.024 Uiso 1 1 calc R U . . . H13B H 0.654200 0.690290 0.300177 0.024 Uiso 1 1 calc R U . . . C14 C 0.70232(12) 0.72621(17) 0.42828(8) 0.0223(3) Uani 1 1 d . . . . . H14A H 0.789897 0.747218 0.416014 0.027 Uiso 1 1 calc R U . . . H14B H 0.668451 0.829234 0.457807 0.027 Uiso 1 1 calc R U . . . C15 C 0.67948(11) 0.54246(16) 0.46903(7) 0.0186(3) Uani 1 1 d . . . . . H15A H 0.755333 0.485258 0.493573 0.022 Uiso 1 1 calc R U . . . H15B H 0.611978 0.543228 0.507464 0.022 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 O1 0.0156(4) 0.0212(5) 0.0453(6) 0.0040(4) 0.0004(4) 0.0003(4) O2 0.0217(4) 0.0190(4) 0.0144(4) 0.0027(3) -0.0033(3) -0.0039(3) O3 0.0246(5) 0.0193(5) 0.0170(4) 0.0040(3) -0.0049(3) -0.0079(4) C1 0.0176(6) 0.0317(8) 0.0558(10) 0.0018(7) -0.0016(6) 0.0039(6) C2 0.0170(6) 0.0176(6) 0.0214(6) -0.0005(5) 0.0008(4) 0.0001(5) C3 0.0164(5) 0.0169(6) 0.0162(5) 0.0005(4) 0.0014(4) -0.0011(4) C4 0.0161(5) 0.0149(6) 0.0140(5) 0.0003(4) 0.0004(4) 0.0005(4) C5 0.0168(5) 0.0150(6) 0.0157(5) 0.0006(4) 0.0006(4) -0.0012(4) C6 0.0148(5) 0.0138(5) 0.0162(5) -0.0010(4) 0.0003(4) 0.0014(4) C7 0.0185(6) 0.0150(6) 0.0140(5) 0.0027(4) 0.0001(4) -0.0018(4) C8 0.0198(6) 0.0177(6) 0.0187(6) -0.0001(5) 0.0002(5) 0.0009(5) C9 0.0275(6) 0.0212(6) 0.0160(6) -0.0020(5) -0.0004(5) -0.0019(5) C10 0.0230(6) 0.0231(6) 0.0181(6) 0.0031(5) -0.0060(5) -0.0030(5) C11 0.0196(6) 0.0234(6) 0.0231(6) 0.0029(5) -0.0019(5) 0.0036(5) C12 0.0214(6) 0.0194(6) 0.0160(5) 0.0004(5) 0.0012(4) 0.0014(5) C13 0.0231(6) 0.0162(6) 0.0206(6) 0.0018(5) 0.0022(5) -0.0007(5) C14 0.0252(6) 0.0169(6) 0.0250(6) -0.0024(5) 0.0018(5) -0.0023(5) C15 0.0207(6) 0.0176(6) 0.0175(6) -0.0018(4) 0.0001(4) -0.0016(5) 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 C2 O1 C1 111.50(10) . . ? C6 O3 H3A 109.5 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 106.66(10) . . ? O1 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C5 C3 C2 123.02(10) . . ? C5 C3 C4 60.58(7) . . ? C2 C3 C4 123.47(10) . . ? C5 C3 H3 113.3 . . ? C2 C3 H3 113.3 . . ? C4 C3 H3 113.3 . . ? C6 C4 C7 115.44(10) . . ? C6 C4 C5 116.90(9) . . ? C7 C4 C5 119.86(10) . . ? C6 C4 C3 117.65(9) . . ? C7 C4 C3 116.93(9) . . ? C5 C4 C3 57.99(7) . . ? C3 C5 C13 124.82(10) . . ? C3 C5 C4 61.43(7) . . ? C13 C5 C4 127.82(10) . . ? C3 C5 C15 123.99(10) . . ? C13 C5 C15 90.86(9) . . ? C4 C5 C15 131.15(10) . . ? O2 C6 O3 122.67(11) . . ? O2 C6 C4 123.57(10) . . ? O3 C6 C4 113.76(10) . . ? C8 C7 C12 119.06(11) . . ? C8 C7 C4 120.40(10) . . ? C12 C7 C4 120.46(10) . . ? C9 C8 C7 120.45(11) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.20(11) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.88(11) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 119.83(11) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 120.58(11) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C5 C13 C14 86.89(9) . . ? C5 C13 H13A 114.2 . . ? C14 C13 H13A 114.2 . . ? C5 C13 H13B 114.2 . . ? C14 C13 H13B 114.2 . . ? H13A C13 H13B 111.3 . . ? C15 C14 C13 89.02(9) . . ? C15 C14 H14A 113.8 . . ? C13 C14 H14A 113.8 . . ? C15 C14 H14B 113.8 . . ? C13 C14 H14B 113.8 . . ? H14A C14 H14B 111.0 . . ? C5 C15 C14 86.77(9) . . ? C5 C15 H15A 114.2 . . ? C14 C15 H15A 114.2 . . ? C5 C15 H15B 114.2 . . ? C14 C15 H15B 114.2 . . ? H15A C15 H15B 111.4 . . ? 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 1.4154(14) . ? O1 C1 1.4213(16) . ? O2 C6 1.2299(14) . ? O3 C6 1.3154(14) . ? O3 H3A 0.889(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.5023(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.4876(16) . ? C3 C4 1.5407(15) . ? C3 H3 1.0000 . ? C4 C6 1.4834(16) . ? C4 C7 1.5044(15) . ? C4 C5 1.5282(16) . ? C5 C13 1.5257(16) . ? C5 C15 1.5311(16) . ? C7 C8 1.3926(17) . ? C7 C12 1.3932(17) . ? C8 C9 1.3898(17) . ? C8 H8 0.9500 . ? C9 C10 1.3857(18) . ? C9 H9 0.9500 . ? C10 C11 1.3911(18) . ? C10 H10 0.9500 . ? C11 C12 1.3918(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.5543(17) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5522(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 C1 O1 C2 C3 -170.95(11) . . . . ? O1 C2 C3 C5 -85.97(13) . . . . ? O1 C2 C3 C4 -160.15(10) . . . . ? C5 C3 C4 C6 -105.95(11) . . . . ? C2 C3 C4 C6 6.21(16) . . . . ? C5 C3 C4 C7 109.94(11) . . . . ? C2 C3 C4 C7 -137.90(11) . . . . ? C2 C3 C4 C5 112.15(13) . . . . ? C2 C3 C5 C13 128.99(12) . . . . ? C4 C3 C5 C13 -118.14(12) . . . . ? C2 C3 C5 C4 -112.87(12) . . . . ? C2 C3 C5 C15 9.57(17) . . . . ? C4 C3 C5 C15 122.44(12) . . . . ? C6 C4 C5 C3 107.25(11) . . . . ? C7 C4 C5 C3 -104.89(11) . . . . ? C6 C4 C5 C13 -139.15(12) . . . . ? C7 C4 C5 C13 8.71(17) . . . . ? C3 C4 C5 C13 113.60(13) . . . . ? C6 C4 C5 C15 -4.44(18) . . . . ? C7 C4 C5 C15 143.42(12) . . . . ? C3 C4 C5 C15 -111.69(14) . . . . ? C7 C4 C6 O2 -167.14(11) . . . . ? C5 C4 C6 O2 -17.87(16) . . . . ? C3 C4 C6 O2 48.22(16) . . . . ? C7 C4 C6 O3 12.61(14) . . . . ? C5 C4 C6 O3 161.89(10) . . . . ? C3 C4 C6 O3 -132.02(11) . . . . ? C6 C4 C7 C8 -96.18(13) . . . . ? C5 C4 C7 C8 115.52(12) . . . . ? C3 C4 C7 C8 48.71(15) . . . . ? C6 C4 C7 C12 80.54(14) . . . . ? C5 C4 C7 C12 -67.76(15) . . . . ? C3 C4 C7 C12 -134.56(11) . . . . ? C12 C7 C8 C9 0.14(18) . . . . ? C4 C7 C8 C9 176.91(11) . . . . ? C7 C8 C9 C10 0.08(19) . . . . ? C8 C9 C10 C11 -0.12(19) . . . . ? C9 C10 C11 C12 -0.06(19) . . . . ? C10 C11 C12 C7 0.29(19) . . . . ? C8 C7 C12 C11 -0.32(18) . . . . ? C4 C7 C12 C11 -177.09(11) . . . . ? C3 C5 C13 C14 -114.55(12) . . . . ? C4 C5 C13 C14 166.84(11) . . . . ? C15 C5 C13 C14 19.20(9) . . . . ? C5 C13 C14 C15 -18.93(9) . . . . ? C3 C5 C15 C14 115.11(12) . . . . ? C13 C5 C15 C14 -19.23(9) . . . . ? C4 C5 C15 C14 -165.07(12) . . . . ? C13 C14 C15 C5 18.86(9) . . . . ?