# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_chenrui_0318 #TrackingRef 'chenrui_0318.cif' _audit_creation_date 2013-03-20 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H24 O4' _chemical_formula_sum 'C18 H24 O4' _chemical_formula_weight 304.37 _chemical_absolute_configuration unk _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'I 1 2 1' _space_group_name_Hall 'I 2y' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z' 3 'x+1/2, y+1/2, z+1/2' 4 '-x+1/2, y+1/2, -z+1/2' _cell_length_a 16.9067(10) _cell_length_b 7.6918(4) _cell_length_c 13.0515(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.576(7) _cell_angle_gamma 90.00 _cell_volume 1662.7(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1213 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.0250 _cell_measurement_theta_min 3.7390 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_unetI/netI 0.0483 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3430 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.19 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9967 _diffrn_measured_fraction_theta_max 0.9104 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -13.00 20.00 1.5000 20.9100 omega____ theta____ kappa____ phi______ frames - -19.3700 -99.0000 -120.0000 22 #__ type_ start__ end____ width___ exp.time_ 2 omega -97.00 -71.50 1.5000 20.9100 omega____ theta____ kappa____ phi______ frames - -19.3700 178.0000 120.0000 17 #__ type_ start__ end____ width___ exp.time_ 3 omega -53.00 40.00 1.5000 20.9100 omega____ theta____ kappa____ phi______ frames - 22.6512 0.0000 -120.0000 62 #__ type_ start__ end____ width___ exp.time_ 4 omega -11.00 79.00 1.5000 20.9100 omega____ theta____ kappa____ phi______ frames - 22.6512 -19.0000 120.0000 60 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0049399000 _diffrn_orient_matrix_UB_12 -0.0236867000 _diffrn_orient_matrix_UB_13 0.0534321000 _diffrn_orient_matrix_UB_21 0.0419945000 _diffrn_orient_matrix_UB_22 0.0170995000 _diffrn_orient_matrix_UB_23 0.0072595000 _diffrn_orient_matrix_UB_31 -0.0068787000 _diffrn_orient_matrix_UB_32 0.0874115000 _diffrn_orient_matrix_UB_33 0.0131101000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2295 _reflns_number_total 2760 _reflns_odcompleteness_completeness 99.67 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.144 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.0(18) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 2760 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0492 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.4885P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1121 _refine_ls_wR_factor_ref 0.1211 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H7A,H7B} of C7, H4 of C4, H3 of C3, H2 of C2, {H13A,H13B} of C13, {H12A, H12B} of C12, H9 of C9, {H8A,H8B} of C8, {H17A,H17B} of C17, H15 of C15 At 1.5 times of: {H11A,H11B,H11C} of C11, {H19A,H19B,H19C} of C19, {H18A,H18B,H18C} of C18 2.a Ternary CH refined with riding coordinates: C9(H9), C15(H15) 2.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.37519(13) 0.5659(3) 0.3969(2) 0.0562(7) Uani 1 1 d . . . O2 O 0.64759(15) -0.0340(4) 0.0572(2) 0.0709(8) Uani 1 1 d . . . O3 O 0.75803(12) 0.2794(3) 0.1875(2) 0.0599(7) Uani 1 1 d . . . O4 O 0.63781(12) 0.3576(3) 0.09331(18) 0.0528(6) Uani 1 1 d . . . C1 C 0.36939(18) 0.3924(4) 0.3707(2) 0.0397(7) Uani 1 1 d . . . C2 C 0.30142(19) 0.2926(5) 0.3708(3) 0.0490(8) Uani 1 1 d . . . H2 H 0.2562 0.3409 0.3902 0.059 Uiso 1 1 calc R . . C3 C 0.30175(18) 0.1206(5) 0.3417(3) 0.0499(8) Uani 1 1 d . . . H3 H 0.2562 0.0524 0.3410 0.060 Uiso 1 1 calc R . . C4 C 0.36873(18) 0.0487(4) 0.3137(3) 0.0442(8) Uani 1 1 d . . . H4 H 0.3680 -0.0680 0.2950 0.053 Uiso 1 1 calc R . . C5 C 0.43763(16) 0.1472(4) 0.3128(2) 0.0334(7) Uani 1 1 d . . . C6 C 0.43863(16) 0.3216(4) 0.3426(2) 0.0363(7) Uani 1 1 d . . . C7 C 0.50980(17) 0.4402(4) 0.3432(3) 0.0448(8) Uani 1 1 d . . . H7A H 0.5222 0.5004 0.4098 0.054 Uiso 1 1 calc R . . H7B H 0.4948 0.5272 0.2889 0.054 Uiso 1 1 calc R . . C8 C 0.58542(17) 0.3469(4) 0.3258(2) 0.0407(7) Uani 1 1 d . . . H8A H 0.6211 0.4294 0.3017 0.049 Uiso 1 1 calc R . . H8B H 0.6139 0.2978 0.3914 0.049 Uiso 1 1 calc R . . C9 C 0.56357(16) 0.2025(4) 0.2453(2) 0.0327(6) Uani 1 1 d . . . H9 H 0.5297 0.2549 0.1833 0.039 Uiso 1 1 calc R . . C10 C 0.51237(15) 0.0614(4) 0.2847(2) 0.0315(6) Uani 1 1 d . . . C11 C 0.55795(17) -0.0322(4) 0.3838(2) 0.0472(8) Uani 1 1 d . . . H11A H 0.5709 0.0499 0.4401 0.071 Uiso 1 1 calc R . . H11B H 0.6068 -0.0820 0.3701 0.071 Uiso 1 1 calc R . . H11C H 0.5245 -0.1225 0.4028 0.071 Uiso 1 1 calc R . . C12 C 0.48764(17) -0.0711(4) 0.1963(3) 0.0436(8) Uani 1 1 d . . . H12A H 0.4560 -0.1625 0.2199 0.052 Uiso 1 1 calc R . . H12B H 0.4537 -0.0140 0.1371 0.052 Uiso 1 1 calc R . . C13 C 0.56010(18) -0.1525(4) 0.1606(3) 0.0506(9) Uani 1 1 d . . . H13A H 0.5885 -0.2273 0.2158 0.061 Uiso 1 1 calc R . . H13B H 0.5408 -0.2246 0.0998 0.061 Uiso 1 1 calc R . . C14 C 0.61764(17) -0.0218(5) 0.1341(3) 0.0441(7) Uani 1 1 d . . . C15 C 0.63867(16) 0.1277(4) 0.2107(2) 0.0356(7) Uani 1 1 d . . . H15 H 0.6743 0.0812 0.2733 0.043 Uiso 1 1 calc R . . C16 C 0.68614(17) 0.2621(4) 0.1648(3) 0.0404(7) Uani 1 1 d . . . C17 C 0.67384(19) 0.4895(5) 0.0384(3) 0.0526(9) Uani 1 1 d . . . H17A H 0.7251 0.4491 0.0248 0.063 Uiso 1 1 calc R . . H17B H 0.6832 0.5948 0.0800 0.063 Uiso 1 1 calc R . . C18 C 0.6165(2) 0.5235(6) -0.0610(3) 0.0695(12) Uani 1 1 d . . . H18A H 0.5636 0.5438 -0.0471 0.104 Uiso 1 1 calc R . . H18B H 0.6149 0.4247 -0.1064 0.104 Uiso 1 1 calc R . . H18C H 0.6338 0.6240 -0.0942 0.104 Uiso 1 1 calc R . . C19 C 0.3113(2) 0.6404(5) 0.4389(3) 0.0607(10) Uani 1 1 d . . . H19A H 0.3061 0.5788 0.5012 0.091 Uiso 1 1 calc R . . H19B H 0.2617 0.6321 0.3883 0.091 Uiso 1 1 calc R . . H19C H 0.3232 0.7603 0.4555 0.091 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 0.0554(14) 0.0414(13) 0.0759(18) -0.0147(14) 0.0229(12) 0.0051(10) O2 0.0810(18) 0.0786(18) 0.0623(16) -0.0217(17) 0.0362(15) -0.0149(16) O3 0.0314(11) 0.0682(15) 0.0767(18) 0.0115(15) 0.0026(11) -0.0071(11) O4 0.0360(11) 0.0635(15) 0.0591(14) 0.0243(13) 0.0101(10) -0.0011(10) C1 0.0402(16) 0.0412(18) 0.0378(17) -0.0002(15) 0.0083(13) 0.0030(13) C2 0.0382(16) 0.056(2) 0.056(2) -0.0012(19) 0.0180(15) 0.0075(15) C3 0.0384(16) 0.054(2) 0.060(2) -0.0021(19) 0.0161(15) -0.0064(15) C4 0.0423(17) 0.0396(17) 0.0523(19) -0.0029(17) 0.0137(15) -0.0039(13) C5 0.0311(14) 0.0365(16) 0.0315(15) 0.0016(14) 0.0041(11) 0.0007(12) C6 0.0370(14) 0.0374(16) 0.0347(15) 0.0002(14) 0.0077(12) 0.0013(12) C7 0.0438(17) 0.0371(17) 0.055(2) -0.0083(17) 0.0128(15) -0.0020(13) C8 0.0390(15) 0.0386(17) 0.0440(17) -0.0065(16) 0.0068(13) -0.0088(13) C9 0.0298(13) 0.0322(14) 0.0352(17) -0.0013(14) 0.0044(11) -0.0010(12) C10 0.0312(14) 0.0318(15) 0.0311(15) -0.0017(14) 0.0052(12) -0.0014(11) C11 0.0460(17) 0.0497(19) 0.0458(19) 0.0107(18) 0.0092(14) 0.0053(16) C12 0.0371(15) 0.0428(18) 0.0516(18) -0.0119(16) 0.0107(14) -0.0080(13) C13 0.0513(18) 0.043(2) 0.060(2) -0.0182(18) 0.0187(16) -0.0093(16) C14 0.0412(16) 0.0489(19) 0.0432(17) -0.0075(18) 0.0108(14) -0.0004(15) C15 0.0314(14) 0.0396(16) 0.0350(16) -0.0004(15) 0.0047(11) 0.0012(13) C16 0.0374(16) 0.0417(18) 0.0435(18) -0.0034(16) 0.0116(14) -0.0018(13) C17 0.0492(18) 0.050(2) 0.063(2) 0.015(2) 0.0239(16) 0.0020(16) C18 0.054(2) 0.089(3) 0.067(3) 0.031(2) 0.0160(18) 0.008(2) C19 0.065(2) 0.053(2) 0.067(3) -0.010(2) 0.0213(19) 0.0127(18) _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 C1 1.376(4) . ? O1 C19 1.425(4) . ? O2 C14 1.215(4) . ? O3 C16 1.199(3) . ? O4 C16 1.331(4) . ? O4 C17 1.445(4) . ? C1 C2 1.382(4) . ? C1 C6 1.405(4) . ? C2 H2 0.9300 . ? C2 C3 1.377(5) . ? C3 H3 0.9300 . ? C3 C4 1.374(4) . ? C4 H4 0.9300 . ? C4 C5 1.392(4) . ? C5 C6 1.396(4) . ? C5 C10 1.534(4) . ? C6 C7 1.509(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.522(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.522(4) . ? C9 H9 0.9800 . ? C9 C10 1.539(4) . ? C9 C15 1.542(4) . ? C10 C11 1.544(4) . ? C10 C12 1.534(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.529(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.488(4) . ? C14 C15 1.518(4) . ? C15 H15 0.9800 . ? C15 C16 1.505(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.480(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C1 O1 C19 117.6(3) . . ? C16 O4 C17 118.3(2) . . ? O1 C1 C2 123.8(3) . . ? O1 C1 C6 114.8(3) . . ? C2 C1 C6 121.4(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C2 C3 H3 119.7 . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C3 C4 H4 119.4 . . ? C3 C4 C5 121.3(3) . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 C10 119.9(2) . . ? C6 C5 C10 121.0(2) . . ? C1 C6 C7 118.0(3) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C7 123.2(3) . . ? C6 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C6 C7 C8 114.0(3) . . ? H7A C7 H7B 107.6 . . ? C8 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C9 C8 C7 110.6(2) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C8 C9 H9 106.9 . . ? C8 C9 C10 111.0(2) . . ? C8 C9 C15 112.0(2) . . ? C10 C9 H9 106.9 . . ? C10 C9 C15 112.7(2) . . ? C15 C9 H9 106.9 . . ? C5 C10 C9 108.8(2) . . ? C5 C10 C11 107.3(2) . . ? C5 C10 C12 110.6(2) . . ? C9 C10 C11 112.9(2) . . ? C12 C10 C9 107.7(2) . . ? C12 C10 C11 109.6(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.0 . . ? C10 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C13 C12 C10 112.8(2) . . ? C13 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C12 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C14 C13 C12 113.3(3) . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? O2 C14 C13 122.7(3) . . ? O2 C14 C15 121.4(3) . . ? C13 C14 C15 115.9(3) . . ? C9 C15 H15 107.2 . . ? C14 C15 C9 112.2(2) . . ? C14 C15 H15 107.2 . . ? C16 C15 C9 113.4(2) . . ? C16 C15 C14 109.3(2) . . ? C16 C15 H15 107.2 . . ? O3 C16 O4 124.1(3) . . ? O3 C16 C15 124.9(3) . . ? O4 C16 C15 110.9(2) . . ? O4 C17 H17A 110.3 . . ? O4 C17 H17B 110.3 . . ? O4 C17 C18 107.0(3) . . ? H17A C17 H17B 108.6 . . ? C18 C17 H17A 110.3 . . ? C18 C17 H17B 110.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 179.1(3) . . . . ? O1 C1 C6 C5 -178.7(3) . . . . ? O1 C1 C6 C7 -0.5(4) . . . . ? O2 C14 C15 C9 137.0(3) . . . . ? O2 C14 C15 C16 10.4(4) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C1 C6 C7 C8 172.3(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? C2 C1 C6 C7 179.2(3) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C3 C4 C5 C10 177.9(3) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C4 C5 C6 C7 -179.3(3) . . . . ? C4 C5 C10 C9 156.8(3) . . . . ? C4 C5 C10 C11 -80.9(3) . . . . ? C4 C5 C10 C12 38.6(4) . . . . ? C5 C6 C7 C8 -9.5(4) . . . . ? C5 C10 C12 C13 176.5(3) . . . . ? C6 C1 C2 C3 -0.6(5) . . . . ? C6 C5 C10 C9 -26.4(4) . . . . ? C6 C5 C10 C11 96.0(3) . . . . ? C6 C5 C10 C12 -144.5(3) . . . . ? C6 C7 C8 C9 38.4(4) . . . . ? C7 C8 C9 C10 -63.6(3) . . . . ? C7 C8 C9 C15 169.5(3) . . . . ? C8 C9 C10 C5 55.8(3) . . . . ? C8 C9 C10 C11 -63.1(3) . . . . ? C8 C9 C10 C12 175.8(2) . . . . ? C8 C9 C15 C14 177.4(3) . . . . ? C8 C9 C15 C16 -58.1(3) . . . . ? C9 C10 C12 C13 57.7(3) . . . . ? C9 C15 C16 O3 132.9(3) . . . . ? C9 C15 C16 O4 -48.5(3) . . . . ? C10 C5 C6 C1 -178.0(3) . . . . ? C10 C5 C6 C7 3.8(4) . . . . ? C10 C9 C15 C14 51.4(3) . . . . ? C10 C9 C15 C16 175.8(2) . . . . ? C10 C12 C13 C14 -52.2(4) . . . . ? C11 C10 C12 C13 -65.4(3) . . . . ? C12 C13 C14 O2 -136.6(3) . . . . ? C12 C13 C14 C15 44.8(4) . . . . ? C13 C14 C15 C9 -44.3(4) . . . . ? C13 C14 C15 C16 -171.0(3) . . . . ? C14 C15 C16 O3 -101.1(4) . . . . ? C14 C15 C16 O4 77.5(3) . . . . ? C15 C9 C10 C5 -177.7(2) . . . . ? C15 C9 C10 C11 63.4(3) . . . . ? C15 C9 C10 C12 -57.7(3) . . . . ? C16 O4 C17 C18 157.2(3) . . . . ? C17 O4 C16 O3 0.7(5) . . . . ? C17 O4 C16 C15 -177.9(3) . . . . ? C19 O1 C1 C2 8.2(5) . . . . ? C19 O1 C1 C6 -172.2(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 931770' ####################################################################### # # 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_p212121 #TrackingRef 'compd 19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 O4' _chemical_formula_weight 282.28 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.850(3) _cell_length_b 12.001(4) _cell_length_c 12.727(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1351.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1169 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 20.79 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details SADABS _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 4965 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2483 _reflns_number_gt 1817 _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^)+(0.0693P)^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 SHELXL _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.8(19) _refine_ls_number_reflns 2483 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 0.7113(3) 0.1692(2) 0.2937(2) 0.0499(7) Uani 1 1 d . . . C2 C 0.7953(4) 0.0814(2) 0.3329(2) 0.0565(9) Uani 1 1 d . . . H2 H 0.7711 0.0083 0.3152 0.068 Uiso 1 1 calc R . . C3 C 0.9151(4) 0.1038(2) 0.3986(2) 0.0582(9) Uani 1 1 d . . . H3 H 0.9718 0.0451 0.4253 0.070 Uiso 1 1 calc R . . C4 C 0.9526(3) 0.2120(2) 0.4255(2) 0.0528(8) Uani 1 1 d . . . H4 H 1.0336 0.2248 0.4703 0.063 Uiso 1 1 calc R . . C5 C 0.8713(3) 0.3015(2) 0.38657(19) 0.0395(6) Uani 1 1 d . . . C6 C 0.7470(3) 0.2795(2) 0.3199(2) 0.0441(7) Uani 1 1 d . . . C7 C 0.6561(3) 0.3705(2) 0.2781(2) 0.0476(7) Uani 1 1 d . . . C8 C 0.7043(3) 0.4828(2) 0.2982(2) 0.0497(7) Uani 1 1 d . . . H8 H 0.6501 0.5410 0.2681 0.060 Uiso 1 1 calc R . . C9 C 0.8237(3) 0.5070(2) 0.35823(19) 0.0383(6) Uani 1 1 d . . . C10 C 0.9081(3) 0.4193(2) 0.42179(19) 0.0377(6) Uani 1 1 d . . . C11 C 1.0785(3) 0.4451(2) 0.4146(2) 0.0469(7) Uani 1 1 d . . . H11A H 1.1335 0.3901 0.4553 0.056 Uiso 1 1 calc R . . H11B H 1.1103 0.4381 0.3420 0.056 Uiso 1 1 calc R . . C12 C 1.1206(3) 0.5612(2) 0.4541(2) 0.0536(8) Uani 1 1 d . . . H12A H 1.1180 0.5624 0.5303 0.064 Uiso 1 1 calc R . . H12B H 1.2224 0.5796 0.4317 0.064 Uiso 1 1 calc R . . C13 C 1.0126(3) 0.6446(2) 0.4117(2) 0.0459(7) Uani 1 1 d . . . C14 C 0.8798(3) 0.6197(2) 0.3688(2) 0.0422(7) Uani 1 1 d . . . C15 C 0.8050(4) 0.7241(2) 0.3320(2) 0.0533(8) Uani 1 1 d . . . H15A H 0.7893 0.7224 0.2566 0.064 Uiso 1 1 calc R . . H15B H 0.7083 0.7344 0.3665 0.064 Uiso 1 1 calc R . . C16 C 1.0321(4) 0.7652(3) 0.4088(3) 0.0587(9) Uani 1 1 d . . . C17 C 0.8541(4) 0.4314(2) 0.5373(2) 0.0506(8) Uani 1 1 d . . . H17A H 0.7500 0.4097 0.5423 0.076 Uiso 1 1 calc R . . H17B H 0.8648 0.5075 0.5592 0.076 Uiso 1 1 calc R . . H17C H 0.9142 0.3844 0.5818 0.076 Uiso 1 1 calc R . . O1 O 0.5941(3) 0.14544(19) 0.2293(2) 0.0728(7) Uani 1 1 d . . . H1 H 0.5479 0.2029 0.2156 0.109 Uiso 1 1 calc R . . O2 O 0.5419(3) 0.35264(19) 0.22282(19) 0.0729(7) Uani 1 1 d . . . O3 O 1.1333(3) 0.8231(2) 0.4397(2) 0.0867(8) Uani 1 1 d . . . O4 O 0.9085(3) 0.81099(17) 0.36059(17) 0.0657(6) 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 0.0529(18) 0.0487(17) 0.0480(16) -0.0040(14) 0.0093(14) -0.0136(15) C2 0.072(2) 0.0398(17) 0.0577(18) -0.0019(14) 0.0198(18) -0.0103(16) C3 0.061(2) 0.0423(17) 0.071(2) 0.0087(14) 0.0112(17) 0.0045(16) C4 0.0531(18) 0.0418(17) 0.0635(18) 0.0045(15) -0.0034(15) 0.0060(14) C5 0.0408(16) 0.0383(14) 0.0395(13) 0.0035(11) 0.0028(11) 0.0000(13) C6 0.0449(16) 0.0467(16) 0.0408(15) 0.0017(12) 0.0042(12) -0.0065(13) C7 0.0427(17) 0.0518(17) 0.0484(15) 0.0024(13) -0.0076(14) -0.0062(14) C8 0.0483(18) 0.0477(17) 0.0529(17) 0.0081(13) -0.0113(15) 0.0084(15) C9 0.0398(15) 0.0387(14) 0.0363(13) 0.0005(11) -0.0027(12) 0.0029(13) C10 0.0377(15) 0.0390(14) 0.0365(13) 0.0016(12) -0.0040(12) 0.0011(12) C11 0.0411(16) 0.0471(15) 0.0526(16) 0.0032(13) -0.0050(14) 0.0028(13) C12 0.0500(19) 0.0487(17) 0.0622(18) 0.0068(14) -0.0136(16) -0.0079(15) C13 0.0548(18) 0.0417(16) 0.0411(15) 0.0014(12) -0.0029(14) -0.0032(13) C14 0.0492(18) 0.0420(15) 0.0354(13) 0.0011(11) -0.0018(13) 0.0041(13) C15 0.067(2) 0.0345(15) 0.0586(17) 0.0010(13) -0.0090(16) 0.0032(15) C16 0.076(2) 0.0437(17) 0.0562(19) -0.0001(14) -0.0028(18) -0.0093(17) C17 0.063(2) 0.0520(17) 0.0365(14) 0.0036(13) 0.0006(14) 0.0017(15) O1 0.0752(17) 0.0642(14) 0.0790(15) -0.0051(13) -0.0164(14) -0.0276(13) O2 0.0597(15) 0.0724(16) 0.0866(16) 0.0020(13) -0.0323(13) -0.0130(12) O3 0.1030(19) 0.0580(14) 0.0992(18) 0.0022(13) -0.0260(17) -0.0295(15) O4 0.0844(16) 0.0396(11) 0.0732(14) 0.0032(11) -0.0098(12) -0.0002(12) _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 1.352(3) . ? C1 C2 1.383(4) . ? C1 C6 1.401(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.414(4) . ? C5 C10 1.519(4) . ? C6 C7 1.457(4) . ? C7 O2 1.250(3) . ? C7 C8 1.436(4) . ? C8 C9 1.337(4) . ? C8 H8 0.9300 . ? C9 C14 1.447(4) . ? C9 C10 1.523(4) . ? C10 C11 1.542(4) . ? C10 C17 1.553(4) . ? C11 C12 1.527(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.486(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.330(4) . ? C13 C16 1.457(4) . ? C14 C15 1.492(4) . ? C15 O4 1.435(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O3 1.200(4) . ? C16 O4 1.369(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O1 H1 0.8200 . ? 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 118.0(3) . . ? O1 C1 C6 121.1(3) . . ? C2 C1 C6 120.8(3) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 118.3(3) . . ? C4 C5 C10 120.3(2) . . ? C6 C5 C10 121.2(2) . . ? C1 C6 C5 119.7(3) . . ? C1 C6 C7 119.8(3) . . ? C5 C6 C7 120.6(2) . . ? O2 C7 C8 120.0(3) . . ? O2 C7 C6 121.6(3) . . ? C8 C7 C6 118.3(2) . . ? C9 C8 C7 122.7(3) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C8 C9 C14 121.9(2) . . ? C8 C9 C10 122.8(2) . . ? C14 C9 C10 115.3(2) . . ? C5 C10 C9 112.4(2) . . ? C5 C10 C11 112.3(2) . . ? C9 C10 C11 108.0(2) . . ? C5 C10 C17 107.5(2) . . ? C9 C10 C17 106.7(2) . . ? C11 C10 C17 109.8(2) . . ? C12 C11 C10 113.7(2) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 109.8(2) . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C16 108.5(3) . . ? C14 C13 C12 124.5(3) . . ? C16 C13 C12 127.0(3) . . ? C13 C14 C9 123.5(3) . . ? C13 C14 C15 109.4(3) . . ? C9 C14 C15 127.1(3) . . ? O4 C15 C14 104.3(2) . . ? O4 C15 H15A 110.9 . . ? C14 C15 H15A 110.9 . . ? O4 C15 H15B 110.9 . . ? C14 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? O3 C16 O4 120.6(3) . . ? O3 C16 C13 130.9(3) . . ? O4 C16 C13 108.4(3) . . ? C10 C17 H17A 109.5 . . ? C10 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C10 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 O1 H1 109.5 . . ? C16 O4 C15 109.4(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 C1 C2 C3 179.9(3) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C3 C4 C5 C10 176.5(3) . . . . ? O1 C1 C6 C5 -179.3(3) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? O1 C1 C6 C7 0.6(4) . . . . ? C2 C1 C6 C7 -179.6(3) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C10 C5 C6 C1 -176.5(2) . . . . ? C4 C5 C6 C7 179.0(3) . . . . ? C10 C5 C6 C7 3.6(4) . . . . ? C1 C6 C7 O2 3.3(4) . . . . ? C5 C6 C7 O2 -176.8(3) . . . . ? C1 C6 C7 C8 -174.1(2) . . . . ? C5 C6 C7 C8 5.8(4) . . . . ? O2 C7 C8 C9 178.7(3) . . . . ? C6 C7 C8 C9 -3.8(4) . . . . ? C7 C8 C9 C14 173.5(3) . . . . ? C7 C8 C9 C10 -7.7(4) . . . . ? C4 C5 C10 C9 171.1(2) . . . . ? C6 C5 C10 C9 -13.6(3) . . . . ? C4 C5 C10 C11 49.1(3) . . . . ? C6 C5 C10 C11 -135.6(2) . . . . ? C4 C5 C10 C17 -71.8(3) . . . . ? C6 C5 C10 C17 103.5(3) . . . . ? C8 C9 C10 C5 15.9(4) . . . . ? C14 C9 C10 C5 -165.3(2) . . . . ? C8 C9 C10 C11 140.4(3) . . . . ? C14 C9 C10 C11 -40.8(3) . . . . ? C8 C9 C10 C17 -101.7(3) . . . . ? C14 C9 C10 C17 77.1(3) . . . . ? C5 C10 C11 C12 -177.4(2) . . . . ? C9 C10 C11 C12 58.1(3) . . . . ? C17 C10 C11 C12 -57.9(3) . . . . ? C10 C11 C12 C13 -45.1(3) . . . . ? C11 C12 C13 C14 15.5(4) . . . . ? C11 C12 C13 C16 -164.0(3) . . . . ? C16 C13 C14 C9 179.7(3) . . . . ? C12 C13 C14 C9 0.1(4) . . . . ? C16 C13 C14 C15 1.5(3) . . . . ? C12 C13 C14 C15 -178.1(3) . . . . ? C8 C9 C14 C13 -167.4(3) . . . . ? C10 C9 C14 C13 13.7(4) . . . . ? C8 C9 C14 C15 10.4(4) . . . . ? C10 C9 C14 C15 -168.4(3) . . . . ? C13 C14 C15 O4 -1.1(3) . . . . ? C9 C14 C15 O4 -179.2(2) . . . . ? C14 C13 C16 O3 179.1(4) . . . . ? C12 C13 C16 O3 -1.3(6) . . . . ? C14 C13 C16 O4 -1.4(4) . . . . ? C12 C13 C16 O4 178.2(3) . . . . ? O3 C16 O4 C15 -179.7(3) . . . . ? C13 C16 O4 C15 0.7(4) . . . . ? C14 C15 O4 C16 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.183 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 926225'