# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_mk473blp21c _database_code_depnum_ccdc_archive 'CCDC 923423' #TrackingRef 'mk473b_mk484b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 F2 O' _chemical_formula_sum 'C15 H10 F2 O' _chemical_formula_weight 244.23 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' F F 0.0171 0.0103 '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_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic 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 6.6609(2) _cell_length_b 9.7886(5) _cell_length_c 18.8033(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.893(3) _cell_angle_gamma 90.00 _cell_volume 1173.09(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4981 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.878 _exptl_crystal_description irregular _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long-fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8538 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2798 _reflns_number_gt 2127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0567P)^2^+0.1515P] 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 2798 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 C1 C 1.24612(19) 0.83093(14) 0.65745(7) 0.0377(3) Uani 1 1 d . . . C2 C 1.07312(17) 0.75040(12) 0.67044(7) 0.0322(3) Uani 1 1 d . . . C3 C 0.90394(18) 0.73477(12) 0.61076(7) 0.0328(3) Uani 1 1 d . . . C11 C 0.71106(17) 0.65630(12) 0.60149(6) 0.0305(3) Uani 1 1 d . . . C12 C 0.69717(19) 0.54323(12) 0.64555(7) 0.0344(3) Uani 1 1 d . . . C13 C 0.51160(19) 0.47158(13) 0.63352(7) 0.0369(3) Uani 1 1 d . . . C14 C 0.34049(18) 0.51440(13) 0.57713(7) 0.0366(3) Uani 1 1 d . . . C15 C 0.34646(18) 0.62286(13) 0.53167(7) 0.0355(3) Uani 1 1 d . . . C16 C 0.53357(18) 0.69270(13) 0.54388(7) 0.0328(3) Uani 1 1 d . . . C21 C 1.09761(17) 0.69819(12) 0.74669(6) 0.0315(3) Uani 1 1 d . . . C22 C 1.26946(19) 0.61708(13) 0.78301(7) 0.0364(3) Uani 1 1 d . . . C23 C 1.2931(2) 0.56876(14) 0.85430(7) 0.0415(3) Uani 1 1 d . . . C24 C 1.1446(2) 0.60422(14) 0.88844(7) 0.0413(3) Uani 1 1 d . . . C25 C 0.9732(2) 0.68389(14) 0.85512(8) 0.0423(3) Uani 1 1 d . . . C26 C 0.95068(19) 0.73149(13) 0.78388(7) 0.0365(3) Uani 1 1 d . . . F1 F 0.15817(12) 0.44361(9) 0.56539(5) 0.0555(3) Uani 1 1 d . . . F2 F 1.16750(16) 0.55745(9) 0.95892(4) 0.0589(3) Uani 1 1 d . . . O1 O 1.41555(14) 0.84967(11) 0.70271(5) 0.0481(3) Uani 1 1 d . . . H1 H 1.215(2) 0.8690(15) 0.6063(8) 0.042(4) Uiso 1 1 d . . . H3 H 0.912(2) 0.7869(14) 0.5653(8) 0.038(3) Uiso 1 1 d . . . H12 H 0.820(2) 0.5135(15) 0.6853(8) 0.039(3) Uiso 1 1 d . . . H13 H 0.501(2) 0.3948(17) 0.6633(8) 0.049(4) Uiso 1 1 d . . . H15 H 0.225(2) 0.6458(15) 0.4920(8) 0.045(4) Uiso 1 1 d . . . H16 H 0.543(2) 0.7693(16) 0.5121(8) 0.045(4) Uiso 1 1 d . . . H22 H 1.373(2) 0.5891(15) 0.7575(8) 0.045(4) Uiso 1 1 d . . . H23 H 1.412(3) 0.5133(17) 0.8808(9) 0.054(4) Uiso 1 1 d . . . H25 H 0.873(3) 0.7041(18) 0.8815(9) 0.060(5) Uiso 1 1 d . . . H26 H 0.827(2) 0.7867(15) 0.7581(7) 0.040(4) 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 C1 0.0366(6) 0.0405(7) 0.0373(7) -0.0069(5) 0.0130(5) -0.0061(5) C2 0.0303(5) 0.0304(6) 0.0362(6) -0.0045(5) 0.0102(5) -0.0006(4) C3 0.0321(6) 0.0310(6) 0.0345(6) -0.0002(5) 0.0085(5) 0.0006(5) C11 0.0301(5) 0.0309(6) 0.0291(6) -0.0028(4) 0.0064(4) 0.0007(4) C12 0.0359(6) 0.0326(6) 0.0292(6) 0.0000(5) 0.0007(5) -0.0001(5) C13 0.0423(7) 0.0344(6) 0.0312(6) 0.0025(5) 0.0060(5) -0.0046(5) C14 0.0315(6) 0.0386(7) 0.0380(7) -0.0019(5) 0.0076(5) -0.0079(5) C15 0.0307(6) 0.0384(7) 0.0331(6) 0.0014(5) 0.0025(5) 0.0016(5) C16 0.0348(6) 0.0321(6) 0.0305(6) 0.0022(5) 0.0078(5) 0.0018(5) C21 0.0297(5) 0.0303(6) 0.0334(6) -0.0071(5) 0.0076(5) -0.0045(4) C22 0.0334(6) 0.0376(7) 0.0383(7) -0.0045(5) 0.0106(5) 0.0010(5) C23 0.0424(7) 0.0401(7) 0.0382(7) -0.0010(6) 0.0055(6) 0.0014(6) C24 0.0572(8) 0.0368(7) 0.0302(6) -0.0057(5) 0.0132(6) -0.0095(6) C25 0.0482(7) 0.0414(7) 0.0433(7) -0.0117(6) 0.0226(6) -0.0063(6) C26 0.0336(6) 0.0362(6) 0.0403(7) -0.0083(5) 0.0119(5) -0.0007(5) F1 0.0382(4) 0.0598(6) 0.0614(6) 0.0116(4) 0.0032(4) -0.0175(4) F2 0.0883(7) 0.0541(5) 0.0364(5) -0.0008(4) 0.0216(4) -0.0077(5) O1 0.0385(5) 0.0606(6) 0.0446(5) -0.0105(5) 0.0115(4) -0.0177(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 C1 O1 1.2138(15) . ? C1 C2 1.4739(17) . ? C1 H1 0.996(14) . ? C2 C3 1.3482(16) . ? C2 C21 1.4857(17) . ? C3 C11 1.4632(16) . ? C3 H3 1.010(14) . ? C11 C16 1.3978(16) . ? C11 C12 1.4016(17) . ? C12 C13 1.3814(17) . ? C12 H12 0.978(14) . ? C13 C14 1.3772(18) . ? C13 H13 0.952(16) . ? C14 F1 1.3594(14) . ? C14 C15 1.3708(18) . ? C15 C16 1.3809(17) . ? C15 H15 0.957(15) . ? C16 H16 0.972(15) . ? C21 C26 1.3967(16) . ? C21 C22 1.3975(17) . ? C22 C23 1.3866(18) . ? C22 H22 0.988(14) . ? C23 C24 1.3710(19) . ? C23 H23 0.970(17) . ? C24 F2 1.3682(14) . ? C24 C25 1.374(2) . ? C25 C26 1.3848(19) . ? C25 H25 0.962(17) . ? C26 H26 0.985(14) . ? 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 C1 C2 125.24(12) . . ? O1 C1 H1 120.7(8) . . ? C2 C1 H1 114.0(8) . . ? C3 C2 C1 115.30(11) . . ? C3 C2 C21 126.51(11) . . ? C1 C2 C21 118.16(10) . . ? C2 C3 C11 130.65(12) . . ? C2 C3 H3 114.1(8) . . ? C11 C3 H3 115.3(8) . . ? C16 C11 C12 118.24(11) . . ? C16 C11 C3 118.31(11) . . ? C12 C11 C3 123.41(10) . . ? C13 C12 C11 120.91(11) . . ? C13 C12 H12 118.9(9) . . ? C11 C12 H12 120.2(9) . . ? C14 C13 C12 118.20(12) . . ? C14 C13 H13 120.6(9) . . ? C12 C13 H13 121.2(9) . . ? F1 C14 C15 118.69(11) . . ? F1 C14 C13 118.05(11) . . ? C15 C14 C13 123.25(11) . . ? C14 C15 C16 117.91(11) . . ? C14 C15 H15 119.8(9) . . ? C16 C15 H15 122.3(9) . . ? C15 C16 C11 121.46(11) . . ? C15 C16 H16 119.6(8) . . ? C11 C16 H16 118.9(8) . . ? C26 C21 C22 118.78(11) . . ? C26 C21 C2 120.43(11) . . ? C22 C21 C2 120.78(10) . . ? C23 C22 C21 120.86(12) . . ? C23 C22 H22 118.4(9) . . ? C21 C22 H22 120.6(9) . . ? C24 C23 C22 118.14(13) . . ? C24 C23 H23 119.6(9) . . ? C22 C23 H23 122.3(9) . . ? F2 C24 C23 118.44(13) . . ? F2 C24 C25 118.39(12) . . ? C23 C24 C25 123.17(12) . . ? C24 C25 C26 118.28(12) . . ? C24 C25 H25 119.5(10) . . ? C26 C25 H25 122.2(10) . . ? C25 C26 C21 120.75(12) . . ? C25 C26 H26 120.1(8) . . ? C21 C26 H26 119.1(8) . . ? 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 C1 C2 C3 -175.47(12) . . . . ? O1 C1 C2 C21 6.13(19) . . . . ? C1 C2 C3 C11 176.03(12) . . . . ? C21 C2 C3 C11 -5.7(2) . . . . ? C2 C3 C11 C16 158.46(13) . . . . ? C2 C3 C11 C12 -24.1(2) . . . . ? C16 C11 C12 C13 -1.51(18) . . . . ? C3 C11 C12 C13 -178.97(12) . . . . ? C11 C12 C13 C14 -0.11(19) . . . . ? C12 C13 C14 F1 179.95(11) . . . . ? C12 C13 C14 C15 1.2(2) . . . . ? F1 C14 C15 C16 -179.31(11) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C14 C15 C16 C11 -1.16(19) . . . . ? C12 C11 C16 C15 2.17(18) . . . . ? C3 C11 C16 C15 179.76(11) . . . . ? C3 C2 C21 C26 -55.16(17) . . . . ? C1 C2 C21 C26 123.04(12) . . . . ? C3 C2 C21 C22 125.98(13) . . . . ? C1 C2 C21 C22 -55.82(16) . . . . ? C26 C21 C22 C23 0.84(18) . . . . ? C2 C21 C22 C23 179.71(11) . . . . ? C21 C22 C23 C24 -0.8(2) . . . . ? C22 C23 C24 F2 -179.67(11) . . . . ? C22 C23 C24 C25 0.7(2) . . . . ? F2 C24 C25 C26 179.78(11) . . . . ? C23 C24 C25 C26 -0.6(2) . . . . ? C24 C25 C26 C21 0.59(19) . . . . ? C22 C21 C26 C25 -0.73(18) . . . . ? C2 C21 C26 C25 -179.60(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.127 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.043 data_mk484bl _database_code_depnum_ccdc_archive 'CCDC 923424' #TrackingRef 'mk473b_mk484b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 O' _chemical_formula_sum 'C15 H12 O' _chemical_formula_weight 208.25 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_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' 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 5.8262(2) _cell_length_b 21.4617(13) _cell_length_c 9.2279(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.017(3) _cell_angle_gamma 90.00 _cell_volume 1149.44(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8135 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long-fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9998 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2625 _reflns_number_gt 1754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0593P)^2^+0.0000P] 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 2625 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C1 C -0.1524(2) 0.23729(7) -0.13820(16) 0.0437(3) Uani 1 1 d . . . C2 C 0.02419(19) 0.18842(6) -0.11676(13) 0.0363(3) Uani 1 1 d . . . C3 C 0.1401(2) 0.17526(6) -0.23237(14) 0.0391(3) Uani 1 1 d . . . C11 C 0.32071(19) 0.12888(6) -0.24924(12) 0.0357(3) Uani 1 1 d . . . C12 C 0.3391(2) 0.07262(7) -0.17338(13) 0.0421(3) Uani 1 1 d . . . C13 C 0.5121(2) 0.03058(8) -0.19785(16) 0.0492(4) Uani 1 1 d . . . C14 C 0.6693(2) 0.04462(8) -0.29776(16) 0.0529(4) Uani 1 1 d . . . C15 C 0.6517(2) 0.09951(8) -0.37426(16) 0.0509(4) Uani 1 1 d . . . C16 C 0.4778(2) 0.14108(8) -0.35174(14) 0.0430(3) Uani 1 1 d . . . C21 C 0.06526(19) 0.16097(6) 0.03122(12) 0.0339(3) Uani 1 1 d . . . C22 C -0.1048(2) 0.12640(7) 0.09130(14) 0.0394(3) Uani 1 1 d . . . C23 C -0.0678(2) 0.10342(7) 0.23157(14) 0.0432(3) Uani 1 1 d . . . C24 C 0.1369(2) 0.11558(7) 0.31414(14) 0.0438(3) Uani 1 1 d . . . C25 C 0.3063(2) 0.14974(7) 0.25563(14) 0.0416(3) Uani 1 1 d . . . C26 C 0.2720(2) 0.17220(6) 0.11452(14) 0.0377(3) Uani 1 1 d . . . O1 O -0.26894(15) 0.25640(5) -0.04477(10) 0.0544(3) Uani 1 1 d . . . H1 H -0.182(2) 0.2558(7) -0.2428(15) 0.053(4) Uiso 1 1 d . . . H3 H 0.103(2) 0.2014(6) -0.3180(13) 0.044(3) Uiso 1 1 d . . . H12 H 0.230(2) 0.0630(7) -0.1018(14) 0.046(3) Uiso 1 1 d . . . H13 H 0.523(2) -0.0105(8) -0.1450(15) 0.054(4) Uiso 1 1 d . . . H14 H 0.790(2) 0.0148(8) -0.3135(15) 0.062(4) Uiso 1 1 d . . . H15 H 0.760(2) 0.1098(8) -0.4459(15) 0.068(5) Uiso 1 1 d . . . H16 H 0.464(2) 0.1805(7) -0.4074(14) 0.044(4) Uiso 1 1 d . . . H22 H -0.253(2) 0.1186(7) 0.0326(14) 0.052(4) Uiso 1 1 d . . . H23 H -0.187(2) 0.0786(7) 0.2738(13) 0.047(3) Uiso 1 1 d . . . H24 H 0.165(2) 0.0990(7) 0.4154(15) 0.049(4) Uiso 1 1 d . . . H25 H 0.452(2) 0.1583(7) 0.3136(14) 0.052(4) Uiso 1 1 d . . . H26 H 0.390(2) 0.1956(6) 0.0738(13) 0.044(4) 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 C1 0.0471(7) 0.0441(9) 0.0397(8) -0.0006(7) 0.0024(6) 0.0054(6) C2 0.0369(6) 0.0375(8) 0.0341(7) -0.0011(6) 0.0014(5) -0.0005(5) C3 0.0457(7) 0.0374(8) 0.0338(7) 0.0031(6) 0.0018(6) 0.0007(6) C11 0.0388(6) 0.0379(8) 0.0302(6) -0.0030(6) 0.0018(5) -0.0016(5) C12 0.0486(7) 0.0389(9) 0.0394(7) -0.0014(6) 0.0075(6) -0.0008(6) C13 0.0590(9) 0.0382(9) 0.0501(8) -0.0017(7) 0.0023(7) 0.0060(7) C14 0.0484(8) 0.0544(11) 0.0562(9) -0.0122(8) 0.0063(7) 0.0097(7) C15 0.0480(8) 0.0590(11) 0.0476(8) -0.0080(7) 0.0139(6) -0.0022(7) C16 0.0495(8) 0.0444(9) 0.0354(7) -0.0020(6) 0.0061(6) -0.0028(6) C21 0.0343(6) 0.0344(8) 0.0333(7) -0.0029(5) 0.0043(5) 0.0021(5) C22 0.0338(7) 0.0440(9) 0.0400(7) -0.0021(6) 0.0006(5) -0.0020(5) C23 0.0441(7) 0.0440(9) 0.0427(7) 0.0029(6) 0.0102(6) -0.0038(6) C24 0.0481(7) 0.0482(9) 0.0350(7) 0.0032(6) 0.0038(6) 0.0039(6) C25 0.0383(7) 0.0471(9) 0.0383(7) -0.0046(6) -0.0026(5) 0.0011(6) C26 0.0354(7) 0.0401(8) 0.0380(7) -0.0024(6) 0.0058(5) -0.0024(5) O1 0.0576(6) 0.0573(7) 0.0490(6) -0.0003(5) 0.0094(5) 0.0187(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 C1 O1 1.2144(15) . ? C1 C2 1.4706(18) . ? C1 H1 1.044(14) . ? C2 C3 1.3417(16) . ? C2 C21 1.4872(16) . ? C3 C11 1.4665(17) . ? C3 H3 0.978(13) . ? C11 C12 1.3952(18) . ? C11 C16 1.3971(16) . ? C12 C13 1.3862(19) . ? C12 H12 0.979(12) . ? C13 C14 1.388(2) . ? C13 H13 1.007(17) . ? C14 C15 1.372(2) . ? C14 H14 0.971(15) . ? C15 C16 1.379(2) . ? C15 H15 0.977(14) . ? C16 H16 0.989(14) . ? C21 C22 1.3913(17) . ? C21 C26 1.3920(16) . ? C22 C23 1.3844(18) . ? C22 H22 0.991(13) . ? C23 C24 1.3829(19) . ? C23 H23 0.981(13) . ? C24 C25 1.3773(19) . ? C24 H24 0.999(14) . ? C25 C26 1.3866(18) . ? C25 H25 0.980(14) . ? C26 H26 0.956(13) . ? 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 C1 C2 124.98(13) . . ? O1 C1 H1 118.0(7) . . ? C2 C1 H1 117.0(7) . . ? C3 C2 C1 115.99(12) . . ? C3 C2 C21 126.51(12) . . ? C1 C2 C21 117.42(10) . . ? C2 C3 C11 130.02(13) . . ? C2 C3 H3 115.5(7) . . ? C11 C3 H3 114.4(7) . . ? C12 C11 C16 118.43(12) . . ? C12 C11 C3 123.94(11) . . ? C16 C11 C3 117.58(12) . . ? C13 C12 C11 120.42(12) . . ? C13 C12 H12 119.9(8) . . ? C11 C12 H12 119.6(8) . . ? C12 C13 C14 119.90(15) . . ? C12 C13 H13 120.5(7) . . ? C14 C13 H13 119.6(7) . . ? C15 C14 C13 120.25(14) . . ? C15 C14 H14 120.7(9) . . ? C13 C14 H14 119.0(9) . . ? C14 C15 C16 120.05(13) . . ? C14 C15 H15 121.2(9) . . ? C16 C15 H15 118.8(9) . . ? C15 C16 C11 120.92(15) . . ? C15 C16 H16 120.1(7) . . ? C11 C16 H16 119.0(7) . . ? C22 C21 C26 118.96(11) . . ? C22 C21 C2 120.94(10) . . ? C26 C21 C2 120.03(11) . . ? C23 C22 C21 120.31(11) . . ? C23 C22 H22 120.5(8) . . ? C21 C22 H22 119.2(8) . . ? C24 C23 C22 120.26(12) . . ? C24 C23 H23 119.3(7) . . ? C22 C23 H23 120.4(7) . . ? C25 C24 C23 119.86(12) . . ? C25 C24 H24 119.5(7) . . ? C23 C24 H24 120.6(8) . . ? C24 C25 C26 120.24(12) . . ? C24 C25 H25 120.2(8) . . ? C26 C25 H25 119.6(8) . . ? C25 C26 C21 120.35(12) . . ? C25 C26 H26 120.2(8) . . ? C21 C26 H26 119.5(8) . . ? 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 C1 C2 C3 -177.81(14) . . . . ? O1 C1 C2 C21 -0.9(2) . . . . ? C1 C2 C3 C11 -178.43(13) . . . . ? C21 C2 C3 C11 5.0(2) . . . . ? C2 C3 C11 C12 29.3(2) . . . . ? C2 C3 C11 C16 -153.26(14) . . . . ? C16 C11 C12 C13 1.17(19) . . . . ? C3 C11 C12 C13 178.60(12) . . . . ? C11 C12 C13 C14 0.4(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C11 1.4(2) . . . . ? C12 C11 C16 C15 -2.09(19) . . . . ? C3 C11 C16 C15 -179.68(12) . . . . ? C3 C2 C21 C22 -118.07(15) . . . . ? C1 C2 C21 C22 65.38(16) . . . . ? C3 C2 C21 C26 65.04(18) . . . . ? C1 C2 C21 C26 -111.51(13) . . . . ? C26 C21 C22 C23 -0.26(19) . . . . ? C2 C21 C22 C23 -177.19(12) . . . . ? C21 C22 C23 C24 1.2(2) . . . . ? C22 C23 C24 C25 -1.2(2) . . . . ? C23 C24 C25 C26 0.3(2) . . . . ? C24 C25 C26 C21 0.6(2) . . . . ? C22 C21 C26 C25 -0.64(19) . . . . ? C2 C21 C26 C25 176.31(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.139 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036