# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_de6bd101_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 O4' _chemical_formula_sum 'C18 H18 O4' _chemical_formula_weight 298.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P12(1)/c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6003(3) _cell_length_b 8.1769(4) _cell_length_c 17.0907(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.409(3) _cell_angle_gamma 90.00 _cell_volume 780.32(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4932 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 29.78 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9443 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12403 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 29.92 _reflns_number_total 2252 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.1896P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2252 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.71331(16) 0.54252(10) 0.86211(5) 0.0328(2) Uani 1 1 d . . . O2 O 0.55109(15) 0.28976(10) 0.86551(5) 0.0318(2) Uani 1 1 d . . . C1 C -0.2700(2) 0.41485(18) 0.56593(7) 0.0392(3) Uani 1 1 d . . . H1A H -0.2141 0.5160 0.5455 0.059 Uiso 1 1 calc R . . H1B H -0.4297 0.4291 0.5816 0.059 Uiso 1 1 calc R . . H1C H -0.2700 0.3319 0.5262 0.059 Uiso 1 1 calc R . . C2 C -0.1087(2) 0.36437(16) 0.63518(7) 0.0315(3) Uani 1 1 d . . . H2 H -0.1459 0.2681 0.6605 0.038 Uiso 1 1 calc R . . C3 C 0.0846(2) 0.44624(15) 0.66365(6) 0.0291(3) Uani 1 1 d . . . H3 H 0.1244 0.5425 0.6388 0.035 Uiso 1 1 calc R . . C4 C 0.2356(2) 0.39286(14) 0.73132(6) 0.0268(2) Uani 1 1 d . . . H4 H 0.2001 0.2934 0.7541 0.032 Uiso 1 1 calc R . . C5 C 0.4231(2) 0.47753(15) 0.76314(6) 0.0285(3) Uani 1 1 d . . . H5 H 0.4656 0.5749 0.7398 0.034 Uiso 1 1 calc R . . C6 C 0.5631(2) 0.42069(13) 0.83397(6) 0.0253(2) Uani 1 1 d . . . C7 C 0.8549(2) 0.51434(14) 0.93238(6) 0.0268(2) Uani 1 1 d . . . C8 C 1.0490(2) 0.41082(15) 0.93395(7) 0.0304(3) Uani 1 1 d . . . H8 H 1.0809 0.3514 0.8895 0.037 Uiso 1 1 calc R . . C9 C 1.1967(2) 0.39611(15) 1.00267(7) 0.0303(3) Uani 1 1 d . . . H9 H 1.3286 0.3268 1.0049 0.036 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 O1 0.0359(5) 0.0329(4) 0.0265(4) 0.0051(3) -0.0166(3) -0.0069(4) O2 0.0333(5) 0.0295(4) 0.0306(4) 0.0016(3) -0.0096(3) -0.0010(3) C1 0.0306(7) 0.0502(8) 0.0344(6) -0.0054(5) -0.0143(5) 0.0021(6) C2 0.0279(6) 0.0364(6) 0.0290(6) -0.0035(4) -0.0066(5) 0.0013(5) C3 0.0286(6) 0.0316(6) 0.0256(5) -0.0017(4) -0.0075(4) 0.0015(5) C4 0.0258(6) 0.0302(5) 0.0233(5) -0.0025(4) -0.0049(4) 0.0023(4) C5 0.0293(6) 0.0311(6) 0.0236(5) 0.0014(4) -0.0075(4) -0.0006(5) C6 0.0237(5) 0.0286(5) 0.0224(5) -0.0018(4) -0.0051(4) 0.0011(4) C7 0.0262(6) 0.0305(5) 0.0219(5) 0.0033(4) -0.0095(4) -0.0051(4) C8 0.0308(6) 0.0356(6) 0.0238(5) -0.0030(4) -0.0045(4) -0.0008(5) C9 0.0248(6) 0.0345(6) 0.0303(6) -0.0015(5) -0.0071(4) 0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C6 1.3672(13) . ? O1 C7 1.4062(12) . ? O2 C6 1.2028(14) . ? C1 C2 1.4909(16) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.3325(16) . ? C2 H2 0.9300 . ? C3 C4 1.4468(15) . ? C3 H3 0.9300 . ? C4 C5 1.3375(16) . ? C4 H4 0.9300 . ? C5 C6 1.4664(14) . ? C5 H5 0.9300 . ? C7 C8 1.3762(17) . ? C7 C9 1.3787(16) 3_767 ? C8 C9 1.3887(15) . ? C8 H8 0.9300 . ? C9 C7 1.3788(16) 3_767 ? C9 H9 0.9300 . ? 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 C6 O1 C7 118.19(9) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 125.19(12) . . ? C3 C2 H2 117.4 . . ? C1 C2 H2 117.4 . . ? C2 C3 C4 123.29(12) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C5 C4 C3 124.13(11) . . ? C5 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C4 C5 C6 121.65(11) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? O2 C6 O1 123.02(10) . . ? O2 C6 C5 127.39(10) . . ? O1 C6 C5 109.58(9) . . ? C8 C7 C9 121.66(10) . 3_767 ? C8 C7 O1 120.67(10) . . ? C9 C7 O1 117.47(10) 3_767 . ? C7 C8 C9 119.20(11) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C7 C9 C8 119.14(11) 3_767 . ? C7 C9 H9 120.4 3_767 . ? C8 C9 H9 120.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.92 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.256 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.041 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.030 ; _database_code_depnum_ccdc_archive 'CCDC 957993' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_de8bd94_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 O4' _chemical_formula_sum 'C22 H26 O4' _chemical_formula_weight 354.43 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4869(3) _cell_length_b 8.0395(4) _cell_length_c 12.2631(8) _cell_angle_alpha 71.633(4) _cell_angle_beta 89.640(3) _cell_angle_gamma 74.810(3) _cell_volume 493.73(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3483 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 30.01 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9235 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4904 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.04 _reflns_number_total 2800 _reflns_number_gt 2423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0807P)^2^+0.0829P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2800 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.14854(16) -0.22618(10) 0.83650(6) 0.0297(2) Uani 1 1 d . . . O2 O 0.27980(15) -0.12102(11) 0.96932(6) 0.0312(2) Uani 1 1 d . . . C1 C 0.8520(3) 0.80109(17) 0.57823(11) 0.0427(3) Uani 1 1 d . . . H1A H 1.0243 0.7669 0.6100 0.064 Uiso 1 1 calc R . . H1B H 0.7677 0.9209 0.5799 0.064 Uiso 1 1 calc R . . H1C H 0.8497 0.8009 0.5000 0.064 Uiso 1 1 calc R . . C2 C 0.7165(2) 0.66582(15) 0.64918(10) 0.0334(2) Uani 1 1 d . . . H2A H 0.5386 0.7077 0.6215 0.040 Uiso 1 1 calc R . . H2B H 0.7278 0.6616 0.7290 0.040 Uiso 1 1 calc R . . C3 C 0.8275(2) 0.47414(15) 0.64308(10) 0.0306(2) Uani 1 1 d . . . H3A H 0.7921 0.4745 0.5656 0.037 Uiso 1 1 calc R . . H3B H 1.0100 0.4398 0.6589 0.037 Uiso 1 1 calc R . . C4 C 0.7221(2) 0.33629(14) 0.72669(9) 0.0282(2) Uani 1 1 d . . . H4 H 0.7580 0.3156 0.8046 0.034 Uiso 1 1 calc R . . C5 C 0.5809(2) 0.23981(14) 0.70008(9) 0.0272(2) Uani 1 1 d . . . H5 H 0.5461 0.2541 0.6230 0.033 Uiso 1 1 calc R . . C6 C 0.48095(19) 0.11362(13) 0.78831(9) 0.0251(2) Uani 1 1 d . . . H6 H 0.5185 0.1036 0.8644 0.030 Uiso 1 1 calc R . . C7 C 0.3397(2) 0.00993(14) 0.77106(9) 0.0274(2) Uani 1 1 d . . . H7 H 0.2948 0.0161 0.6966 0.033 Uiso 1 1 calc R . . C8 C 0.25629(19) -0.11374(13) 0.87076(8) 0.0237(2) Uani 1 1 d . . . C9 C 0.07478(19) -0.36220(13) 0.92270(8) 0.0246(2) Uani 1 1 d . . . C10 C 0.1837(2) -0.53987(14) 0.92679(9) 0.0290(2) Uani 1 1 d . . . H10 H 0.3068 -0.5651 0.8774 0.035 Uiso 1 1 calc R . . C11 C -0.1081(2) -0.31926(14) 0.99485(9) 0.0289(2) Uani 1 1 d . . . H11 H -0.1791 -0.1989 0.9911 0.035 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 O1 0.0438(4) 0.0265(4) 0.0240(4) -0.0068(3) 0.0061(3) -0.0200(3) O2 0.0391(4) 0.0354(4) 0.0252(4) -0.0101(3) 0.0071(3) -0.0202(3) C1 0.0579(8) 0.0314(6) 0.0403(6) -0.0061(5) 0.0054(6) -0.0216(6) C2 0.0357(5) 0.0275(5) 0.0376(6) -0.0093(4) 0.0067(4) -0.0113(4) C3 0.0324(5) 0.0276(5) 0.0326(5) -0.0073(4) 0.0122(4) -0.0129(4) C4 0.0299(5) 0.0258(5) 0.0285(5) -0.0065(4) 0.0091(4) -0.0101(4) C5 0.0321(5) 0.0237(5) 0.0251(5) -0.0058(4) 0.0076(4) -0.0094(4) C6 0.0279(5) 0.0213(4) 0.0251(4) -0.0057(4) 0.0061(3) -0.0075(3) C7 0.0345(5) 0.0241(5) 0.0237(4) -0.0049(4) 0.0045(4) -0.0117(4) C8 0.0247(4) 0.0206(4) 0.0261(4) -0.0070(3) 0.0036(3) -0.0075(3) C9 0.0295(5) 0.0224(4) 0.0235(4) -0.0056(3) 0.0033(3) -0.0122(4) C10 0.0321(5) 0.0259(5) 0.0326(5) -0.0123(4) 0.0116(4) -0.0109(4) C11 0.0318(5) 0.0205(4) 0.0348(5) -0.0092(4) 0.0077(4) -0.0076(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C8 1.3658(11) . ? O1 C9 1.4054(11) . ? O2 C8 1.1976(12) . ? C1 C2 1.5206(16) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.5268(15) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.4921(13) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.3363(14) . ? C4 H4 0.9300 . ? C5 C6 1.4467(13) . ? C5 H5 0.9300 . ? C6 C7 1.3387(14) . ? C6 H6 0.9300 . ? C7 C8 1.4691(13) . ? C7 H7 0.9300 . ? C9 C10 1.3812(14) . ? C9 C11 1.3817(14) . ? C10 C11 1.3903(14) 2_547 ? C10 H10 0.9300 . ? C11 C10 1.3904(14) 2_547 ? C11 H11 0.9300 . ? 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 C8 O1 C9 117.62(8) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 112.58(10) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 112.40(9) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 126.11(10) . . ? C5 C4 H4 116.9 . . ? C3 C4 H4 116.9 . . ? C4 C5 C6 121.55(9) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 126.30(10) . . ? C7 C6 H6 116.9 . . ? C5 C6 H6 116.9 . . ? C6 C7 C8 119.44(9) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? O2 C8 O1 123.13(9) . . ? O2 C8 C7 126.50(9) . . ? O1 C8 C7 110.36(8) . . ? C10 C9 C11 121.90(9) . . ? C10 C9 O1 116.44(9) . . ? C11 C9 O1 121.55(9) . . ? C9 C10 C11 119.62(9) . 2_547 ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 2_547 . ? C9 C11 C10 118.48(9) . 2_547 ? C9 C11 H11 120.8 . . ? C10 C11 H11 120.8 2_547 . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.357 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.101 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.033 ; _database_code_depnum_ccdc_archive 'CCDC 957994'