#------------------------------------------------------------------------------ #$Date: 2018-05-25 14:46:31 +0300 (Fri, 25 May 2018) $ #$Revision: 207975 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549463.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_1549463 loop_ _publ_author_name 'Salvati, Anna E.' 'Law, James A.' 'Liriano, Jouse' 'Frederich, Jim' _publ_section_title ; Modular access to functionalized 5-8-5 ring systems via a photoinduced cycloisomerization reaction ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC00999F _journal_year 2018 _chemical_formula_moiety 'C15 H20 O2' _chemical_formula_sum 'C15 H20 O2' _chemical_formula_weight 232.31 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-01-11 deposited with the CCDC. 2018-05-23 downloaded from the CCDC. ; _cell_angle_alpha 106.4923(11) _cell_angle_beta 92.7147(11) _cell_angle_gamma 108.8989(10) _cell_formula_units_Z 2 _cell_length_a 6.8954(6) _cell_length_b 8.3622(8) _cell_length_c 12.1458(11) _cell_measurement_reflns_used 3078 _cell_measurement_temperature 203(2) _cell_measurement_theta_max 29.04 _cell_measurement_theta_min 2.71 _cell_volume 627.79(10) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 203(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_unetI/netI 0.0191 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _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 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6802 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 1.770 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.7070 _exptl_absorpt_correction_type empirical _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.229 _exptl_crystal_description irregular _exptl_crystal_F_000 252 _exptl_crystal_size_max 0.216 _exptl_crystal_size_mid 0.215 _exptl_crystal_size_min 0.180 _exptl_transmission_factor_max 0.7458 _exptl_transmission_factor_min 0.7070 _refine_diff_density_max 0.261 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2566 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0393 _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^)+(0.0378P)^2^+0.2556P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0908 _refine_ls_wR_factor_ref 0.0954 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2170 _reflns_number_total 2566 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc00999f2.cif _cod_data_source_block fred30c _cod_original_cell_volume 627.78(10) _cod_database_code 1549463 _shelx_shelxl_version_number 2014/7 _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 0.983 _shelx_estimated_absorpt_t_max 0.986 _exptl_absorpt_special_details SADABS _shelx_res_file ; fred30c.res created by SHELXL-2014/7 TITL fred30cc in P-1 CELL 0.71073 6.89540 8.36220 12.14580 106.4923 92.7147 108.8989 ZERR 2.00 0.00060 0.00080 0.00110 0.0011 0.0011 0.0010 LATT 1 SFAC C H O UNIT 30 40 4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 10 HTAB O1 O2_$1 HTAB O1 O2_$1 EQIV $1 -x+1, -y+1, -z+1 CONF HTAB SIZE 0.18 0.215 0.216 HTAB O1 O2_$1 HTAB O1 O2_$1 TEMP -70.000 WGHT 0.037800 0.255600 FVAR 0.42932 MOLE 1 C1 1 0.362075 0.592122 0.780253 11.00000 0.02591 0.02524 = 0.02548 0.00787 0.00275 0.00632 C2 1 0.167785 0.546249 0.840238 11.00000 0.02834 0.03176 = 0.03950 0.00931 0.00755 0.00658 AFIX 23 H2A 2 0.070797 0.599576 0.818354 11.00000 -1.20000 H2B 2 0.096926 0.416849 0.817082 11.00000 -1.20000 AFIX 0 C3 1 0.242794 0.621956 0.971226 11.00000 0.03792 0.05439 = 0.03730 0.01368 0.01262 0.01048 AFIX 23 H3A 2 0.222648 0.525487 1.005088 11.00000 -1.20000 H3B 2 0.166493 0.697307 1.009346 11.00000 -1.20000 AFIX 0 C4 1 0.474368 0.732185 0.986125 11.00000 0.03718 0.03287 = 0.02622 0.00494 0.00652 0.00831 AFIX 23 H4A 2 0.510016 0.844781 1.049526 11.00000 -1.20000 H4B 2 0.559549 0.666036 1.003485 11.00000 -1.20000 AFIX 0 C5 1 0.509750 0.766976 0.870061 11.00000 0.02919 0.02148 = 0.02621 0.00491 0.00385 0.00834 AFIX 13 H5 2 0.457763 0.863394 0.867477 11.00000 -1.20000 AFIX 0 C6 1 0.741025 0.830065 0.859458 11.00000 0.02698 0.02242 = 0.02455 0.00371 -0.00054 0.00480 AFIX 23 H6A 2 0.794899 0.739040 0.869053 11.00000 -1.20000 H6B 2 0.811286 0.938471 0.925078 11.00000 -1.20000 AFIX 0 C7 1 0.806393 0.869903 0.748441 11.00000 0.02424 0.02065 = 0.02696 0.00596 0.00083 0.00541 C8 1 0.798605 0.710281 0.646414 11.00000 0.02102 0.02570 = 0.02510 0.00736 -0.00004 0.00815 C9 1 0.716384 0.533365 0.624436 11.00000 0.02928 0.02587 = 0.02569 0.00450 0.00324 0.01064 AFIX 43 H9 2 0.739403 0.466685 0.553058 11.00000 -1.20000 AFIX 0 C10 1 0.597405 0.424580 0.690854 11.00000 0.03544 0.01874 = 0.03360 0.00671 0.00349 0.00885 AFIX 43 H10 2 0.627062 0.320685 0.685133 11.00000 -1.20000 AFIX 0 C11 1 0.454172 0.446850 0.758140 11.00000 0.03248 0.02010 = 0.02730 0.00749 0.00189 0.00367 AFIX 43 H11 2 0.404743 0.361728 0.796350 11.00000 -1.20000 AFIX 0 C12 1 1.042107 0.981708 0.769623 11.00000 0.02653 0.02567 = 0.03337 0.00720 -0.00002 0.00203 AFIX 23 H12A 2 1.067643 1.107098 0.811931 11.00000 -1.20000 H12B 2 1.120955 0.936354 0.814564 11.00000 -1.20000 AFIX 0 C13 1 1.104168 0.961343 0.648144 11.00000 0.02626 0.03076 = 0.03778 0.01204 0.00441 0.00453 AFIX 23 H13A 2 1.088089 1.054881 0.618905 11.00000 -1.20000 H13B 2 1.248228 0.966357 0.649009 11.00000 -1.20000 AFIX 0 C14 1 0.955508 0.779671 0.574905 11.00000 0.02666 0.03016 = 0.03054 0.01168 0.00338 0.01187 C15 1 0.686804 0.975638 0.708495 11.00000 0.03534 0.02804 = 0.03838 0.01335 0.00771 0.01401 AFIX 137 H15A 2 0.747681 1.015314 0.646212 11.00000 -1.50000 H15B 2 0.694725 1.078273 0.773282 11.00000 -1.50000 H15C 2 0.542735 0.899876 0.680848 11.00000 -1.50000 AFIX 0 O1 3 0.316146 0.626058 0.675081 11.00000 0.03222 0.03091 = 0.02821 0.00869 -0.00352 0.00677 AFIX 147 H1 2 0.235182 0.532870 0.626997 11.00000 -1.50000 AFIX 0 O2 3 0.967752 0.703546 0.474806 11.00000 0.03683 0.03801 = 0.03099 0.00941 0.00953 0.01007 HKLF 4 REM fred30cc in P-1 REM R1 = 0.0393 for 2170 Fo > 4sig(Fo) and 0.0463 for all 2566 data REM 156 parameters refined using 0 restraints END WGHT 0.0518 0.1677 REM Instructions for potential hydrogen bonds HTAB O1 O2_$1 REM Highest difference peak 0.261, deepest hole -0.159, 1-sigma level 0.036 Q1 1 0.6182 0.7899 0.8563 11.00000 0.05 0.26 Q2 1 0.9153 0.9259 0.7571 11.00000 0.05 0.24 Q3 1 0.4477 0.6739 0.8281 11.00000 0.05 0.24 Q4 1 0.7887 0.7866 0.6967 11.00000 0.05 0.22 Q5 1 0.2518 0.5618 0.8047 11.00000 0.05 0.21 Q6 1 0.7479 0.9215 0.7321 11.00000 0.05 0.21 Q7 1 0.8838 0.7369 0.6112 11.00000 0.05 0.20 Q8 1 0.4972 0.7518 0.9270 11.00000 0.05 0.18 Q9 1 0.7761 0.8500 0.7978 11.00000 0.05 0.18 Q10 1 0.8124 0.6261 0.6620 11.00000 0.05 0.18 ; _shelx_res_checksum 94594 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 C1 C 0.36207(19) 0.59212(17) 0.78025(11) 0.0263(3) Uani 1 1 d . . C2 C 0.1678(2) 0.54625(19) 0.84024(13) 0.0346(3) Uani 1 1 d . . H2A H 0.0708 0.5996 0.8184 0.042 Uiso 1 1 calc R U H2B H 0.0969 0.4168 0.8171 0.042 Uiso 1 1 calc R U C3 C 0.2428(2) 0.6220(2) 0.97123(14) 0.0446(4) Uani 1 1 d . . H3A H 0.2226 0.5255 1.0051 0.054 Uiso 1 1 calc R U H3B H 0.1665 0.6973 1.0093 0.054 Uiso 1 1 calc R U C4 C 0.4744(2) 0.73219(19) 0.98612(12) 0.0341(3) Uani 1 1 d . . H4A H 0.5100 0.8448 1.0495 0.041 Uiso 1 1 calc R U H4B H 0.5595 0.6660 1.0035 0.041 Uiso 1 1 calc R U C5 C 0.5098(2) 0.76698(16) 0.87006(11) 0.0264(3) Uani 1 1 d . . H5 H 0.4578 0.8634 0.8675 0.032 Uiso 1 1 calc R U C6 C 0.74102(19) 0.83007(17) 0.85946(11) 0.0266(3) Uani 1 1 d . . H6A H 0.7949 0.7390 0.8691 0.032 Uiso 1 1 calc R U H6B H 0.8113 0.9385 0.9251 0.032 Uiso 1 1 calc R U C7 C 0.80639(19) 0.86990(16) 0.74844(11) 0.0251(3) Uani 1 1 d . . C8 C 0.79860(18) 0.71028(16) 0.64641(11) 0.0242(3) Uani 1 1 d . . C9 C 0.7164(2) 0.53336(17) 0.62444(11) 0.0276(3) Uani 1 1 d . . H9 H 0.7394 0.4667 0.5531 0.033 Uiso 1 1 calc R U C10 C 0.5974(2) 0.42458(17) 0.69085(12) 0.0299(3) Uani 1 1 d . . H10 H 0.6271 0.3207 0.6851 0.036 Uiso 1 1 calc R U C11 C 0.4542(2) 0.44685(16) 0.75814(11) 0.0282(3) Uani 1 1 d . . H11 H 0.4047 0.3617 0.7964 0.034 Uiso 1 1 calc R U C12 C 1.0421(2) 0.98171(17) 0.76962(12) 0.0310(3) Uani 1 1 d . . H12A H 1.0676 1.1071 0.8119 0.037 Uiso 1 1 calc R U H12B H 1.1210 0.9364 0.8146 0.037 Uiso 1 1 calc R U C13 C 1.1042(2) 0.96134(18) 0.64814(12) 0.0328(3) Uani 1 1 d . . H13A H 1.0881 1.0549 0.6189 0.039 Uiso 1 1 calc R U H13B H 1.2482 0.9664 0.6490 0.039 Uiso 1 1 calc R U C14 C 0.9555(2) 0.77967(18) 0.57490(12) 0.0282(3) Uani 1 1 d . . C15 C 0.6868(2) 0.97564(18) 0.70849(13) 0.0325(3) Uani 1 1 d . . H15A H 0.7477 1.0153 0.6462 0.049 Uiso 1 1 calc R U H15B H 0.6947 1.0783 0.7733 0.049 Uiso 1 1 calc R U H15C H 0.5427 0.8999 0.6808 0.049 Uiso 1 1 calc R U O1 O 0.31615(15) 0.62606(12) 0.67508(8) 0.0320(2) Uani 1 1 d . . H1 H 0.2352 0.5329 0.6270 0.048 Uiso 1 1 calc R U O2 O 0.96775(15) 0.70355(13) 0.47481(8) 0.0363(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 C1 0.0259(6) 0.0252(6) 0.0255(6) 0.0079(5) 0.0027(5) 0.0063(5) C2 0.0283(7) 0.0318(7) 0.0395(8) 0.0093(6) 0.0075(6) 0.0066(6) C3 0.0379(8) 0.0544(10) 0.0373(8) 0.0137(7) 0.0126(7) 0.0105(7) C4 0.0372(8) 0.0329(7) 0.0262(7) 0.0049(6) 0.0065(6) 0.0083(6) C5 0.0292(7) 0.0215(6) 0.0262(7) 0.0049(5) 0.0039(5) 0.0083(5) C6 0.0270(6) 0.0224(6) 0.0246(6) 0.0037(5) -0.0005(5) 0.0048(5) C7 0.0242(6) 0.0207(6) 0.0270(6) 0.0060(5) 0.0008(5) 0.0054(5) C8 0.0210(6) 0.0257(6) 0.0251(6) 0.0074(5) 0.0000(5) 0.0081(5) C9 0.0293(7) 0.0259(6) 0.0257(6) 0.0045(5) 0.0032(5) 0.0106(5) C10 0.0354(7) 0.0187(6) 0.0336(7) 0.0067(5) 0.0035(6) 0.0088(5) C11 0.0325(7) 0.0201(6) 0.0273(7) 0.0075(5) 0.0019(5) 0.0037(5) C12 0.0265(7) 0.0257(7) 0.0334(7) 0.0072(6) 0.0000(5) 0.0020(5) C13 0.0263(7) 0.0308(7) 0.0378(8) 0.0120(6) 0.0044(6) 0.0045(6) C14 0.0267(7) 0.0302(7) 0.0305(7) 0.0117(6) 0.0034(5) 0.0119(5) C15 0.0353(7) 0.0280(7) 0.0384(8) 0.0134(6) 0.0077(6) 0.0140(6) O1 0.0322(5) 0.0309(5) 0.0282(5) 0.0087(4) -0.0035(4) 0.0068(4) O2 0.0368(5) 0.0380(6) 0.0310(5) 0.0094(4) 0.0095(4) 0.0101(4) 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 O1 C1 C11 110.93(10) O1 C1 C2 111.23(11) C11 C1 C2 111.23(11) O1 C1 C5 109.16(10) C11 C1 C5 111.47(10) C2 C1 C5 102.54(10) C3 C2 C1 106.91(11) C3 C2 H2A 110.3 C1 C2 H2A 110.3 C3 C2 H2B 110.3 C1 C2 H2B 110.3 H2A C2 H2B 108.6 C2 C3 C4 105.87(11) C2 C3 H3A 110.6 C4 C3 H3A 110.6 C2 C3 H3B 110.6 C4 C3 H3B 110.6 H3A C3 H3B 108.7 C5 C4 C3 105.72(11) C5 C4 H4A 110.6 C3 C4 H4A 110.6 C5 C4 H4B 110.6 C3 C4 H4B 110.6 H4A C4 H4B 108.7 C4 C5 C6 111.51(11) C4 C5 C1 102.80(10) C6 C5 C1 118.73(10) C4 C5 H5 107.8 C6 C5 H5 107.8 C1 C5 H5 107.8 C5 C6 C7 118.97(11) C5 C6 H6A 107.6 C7 C6 H6A 107.6 C5 C6 H6B 107.6 C7 C6 H6B 107.6 H6A C6 H6B 107.0 C8 C7 C6 116.19(10) C8 C7 C15 109.84(10) C6 C7 C15 111.85(11) C8 C7 C12 100.01(10) C6 C7 C12 110.04(10) C15 C7 C12 108.04(10) C9 C8 C14 118.16(12) C9 C8 C7 133.52(12) C14 C8 C7 106.78(10) C8 C9 C10 132.05(12) C8 C9 H9 114.0 C10 C9 H9 114.0 C11 C10 C9 131.44(12) C11 C10 H10 114.3 C9 C10 H10 114.3 C10 C11 C1 127.92(12) C10 C11 H11 116.0 C1 C11 H11 116.0 C13 C12 C7 105.28(10) C13 C12 H12A 110.7 C7 C12 H12A 110.7 C13 C12 H12B 110.7 C7 C12 H12B 110.7 H12A C12 H12B 108.8 C14 C13 C12 103.80(11) C14 C13 H13A 111.0 C12 C13 H13A 111.0 C14 C13 H13B 111.0 C12 C13 H13B 111.0 H13A C13 H13B 109.0 O2 C14 C8 126.81(12) O2 C14 C13 124.65(12) C8 C14 C13 108.52(11) C7 C15 H15A 109.5 C7 C15 H15B 109.5 H15A C15 H15B 109.5 C7 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C1 O1 H1 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.4277(15) C1 C11 1.5106(18) C1 C2 1.5463(18) C1 C5 1.5458(17) C2 C3 1.529(2) C2 H2A 0.9800 C2 H2B 0.9800 C3 C4 1.535(2) C3 H3A 0.9800 C3 H3B 0.9800 C4 C5 1.5332(18) C4 H4A 0.9800 C4 H4B 0.9800 C5 C6 1.5333(18) C5 H5 0.9900 C6 C7 1.5322(18) C6 H6A 0.9800 C6 H6B 0.9800 C7 C8 1.5259(17) C7 C15 1.5411(18) C7 C12 1.5561(17) C8 C9 1.3414(18) C8 C14 1.4933(18) C9 C10 1.4653(19) C9 H9 0.9400 C10 C11 1.3369(19) C10 H10 0.9400 C11 H11 0.9400 C12 C13 1.5341(19) C12 H12A 0.9800 C12 H12B 0.9800 C13 C14 1.5125(19) C13 H13A 0.9800 C13 H13B 0.9800 C14 O2 1.2229(16) C15 H15A 0.9700 C15 H15B 0.9700 C15 H15C 0.9700 O1 H1 0.8300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666 O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666 O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666 O1 H1 O2 0.83 2.01 2.8393(14) 173.7 2_666 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 O1 C1 C2 C3 -145.93(12) C11 C1 C2 C3 89.88(14) C5 C1 C2 C3 -29.38(14) C1 C2 C3 C4 7.46(16) C2 C3 C4 C5 17.78(16) C3 C4 C5 C6 -164.29(12) C3 C4 C5 C1 -36.02(14) O1 C1 C5 C4 157.81(11) C11 C1 C5 C4 -79.31(13) C2 C1 C5 C4 39.77(13) O1 C1 C5 C6 -78.60(14) C11 C1 C5 C6 44.28(15) C2 C1 C5 C6 163.37(11) C4 C5 C6 C7 179.44(11) C1 C5 C6 C7 60.26(16) C5 C6 C7 C8 -83.69(14) C5 C6 C7 C15 43.53(15) C5 C6 C7 C12 163.62(11) C6 C7 C8 C9 12.1(2) C15 C7 C8 C9 -116.12(16) C12 C7 C8 C9 130.43(15) C6 C7 C8 C14 -152.97(11) C15 C7 C8 C14 78.82(12) C12 C7 C8 C14 -34.63(12) C14 C8 C9 C10 164.99(13) C7 C8 C9 C10 1.2(3) C8 C9 C10 C11 36.6(2) C9 C10 C11 C1 3.9(2) O1 C1 C11 C10 42.73(18) C2 C1 C11 C10 167.09(13) C5 C1 C11 C10 -79.14(17) C8 C7 C12 C13 39.15(13) C6 C7 C12 C13 161.94(11) C15 C7 C12 C13 -75.68(13) C7 C12 C13 C14 -29.17(13) C9 C8 C14 O2 28.7(2) C7 C8 C14 O2 -163.52(13) C9 C8 C14 C13 -149.82(12) C7 C8 C14 C13 17.93(13) C12 C13 C14 O2 -171.38(13) C12 C13 C14 C8 7.21(14)