Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 _publ_contact_author_name 'Bardeen, Christopher' _publ_contact_author_email christopher.bardeen@ucr.edu _publ_contact_author_address ; ; loop_ _publ_author_name 'Zhu, Lingyan' 'Agarwal, Arun' 'Lai, Jinfeng' 'Al-Kaysi, Rabih' 'Tham, Fook' 'Ghaddar, Tarek' 'Mueller, Lenoard' 'Bardeen, Christopher' # Attachment 'PRD_cb14_new_dimer_0m.cif' data_cb14_new_dimer_0m _database_code_depnum_ccdc_archive 'CCDC 808561' #TrackingRef 'PRD_cb14_new_dimer_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 O2' _chemical_formula_weight 278.33 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1177(15) _cell_length_b 17.457(3) _cell_length_c 9.9165(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.715(2) _cell_angle_gamma 90.00 _cell_volume 1550.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3887 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.32 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 15780 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2741 _reflns_number_gt 1635 _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^)+(0.0827P)^2^+0.5170P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2741 _refine_ls_number_parameters 386 _refine_ls_number_restraints 769 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 0.957 _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 -0.0935(6) 0.1442(2) 0.3388(5) 0.0780(11) Uani 0.808(3) 1 d PU A 1 H1A H -0.1384 0.1869 0.3701 0.094 Uiso 0.808(3) 1 calc PR A 1 C2 C -0.1494(7) 0.1164(3) 0.2135(5) 0.0926(12) Uani 0.808(3) 1 d PU A 1 H2A H -0.2308 0.1401 0.1591 0.111 Uiso 0.808(3) 1 calc PR A 1 C3 C -0.0842(7) 0.0508(3) 0.1640(5) 0.0955(13) Uani 0.808(3) 1 d PU A 1 H3A H -0.1238 0.0311 0.0778 0.115 Uiso 0.808(3) 1 calc PR A 1 C4 C 0.0343(7) 0.0173(3) 0.2414(5) 0.0836(13) Uani 0.808(3) 1 d PU A 1 H4A H 0.0754 -0.0256 0.2071 0.100 Uiso 0.808(3) 1 calc PR A 1 C4A C 0.0998(5) 0.0446(2) 0.3735(4) 0.0664(10) Uani 0.808(3) 1 d PU A 1 C5 C 0.4098(5) 0.0013(2) 0.6649(5) 0.0824(11) Uani 0.808(3) 1 d PU A 1 H5A H 0.4527 -0.0411 0.6308 0.099 Uiso 0.808(3) 1 calc PR A 1 C6 C 0.4682(5) 0.0275(3) 0.7908(5) 0.0948(12) Uani 0.808(3) 1 d PU A 1 H6A H 0.5507 0.0034 0.8427 0.114 Uiso 0.808(3) 1 calc PR A 1 C7 C 0.4036(5) 0.0922(2) 0.8448(5) 0.0924(12) Uani 0.808(3) 1 d PU A 1 H7A H 0.4446 0.1102 0.9320 0.111 Uiso 0.808(3) 1 calc PR A 1 C8 C 0.2838(5) 0.1277(2) 0.7711(5) 0.0782(10) Uani 0.808(3) 1 d PU A 1 H8A H 0.2431 0.1696 0.8088 0.094 Uiso 0.808(3) 1 calc PR A 1 C8A C 0.2177(4) 0.10255(18) 0.6365(4) 0.0615(8) Uani 0.808(3) 1 d PU A 1 C9 C 0.0920(3) 0.13707(13) 0.5557(3) 0.0574(7) Uani 0.808(3) 1 d PU A 1 C9A C 0.0324(4) 0.1106(2) 0.4255(4) 0.0631(9) Uani 0.808(3) 1 d PU A 1 C10 C 0.2204(4) 0.01030(16) 0.4523(4) 0.0674(9) Uani 0.808(3) 1 d PU A 1 H10A H 0.2619 -0.0324 0.4178 0.081 Uiso 0.808(3) 1 calc PR A 1 C10A C 0.2836(4) 0.03690(17) 0.5823(4) 0.0649(8) Uani 0.808(3) 1 d PU A 1 C11 C 0.0239(4) 0.20581(18) 0.6121(4) 0.0680(11) Uani 0.808(3) 1 d PDU A 1 O1 O 0.0624(5) 0.26925(15) 0.6015(5) 0.158(2) Uani 0.808(3) 1 d PDU A 1 O2 O -0.0838(9) 0.1863(3) 0.6759(7) 0.0903(16) Uani 0.808(3) 1 d PDU A 1 C12 C -0.1739(6) 0.2420(3) 0.7405(6) 0.0798(16) Uani 0.808(3) 1 d PDU A 1 C13 C -0.2388(6) 0.3043(3) 0.6416(5) 0.1331(18) Uani 0.808(3) 1 d PDU A 1 H13A H -0.2845 0.2818 0.5558 0.200 Uiso 0.808(3) 1 calc PR A 1 H13B H -0.1607 0.3385 0.6270 0.200 Uiso 0.808(3) 1 calc PR A 1 H13C H -0.3124 0.3324 0.6792 0.200 Uiso 0.808(3) 1 calc PR A 1 C14 C -0.2997(6) 0.1957(3) 0.7767(7) 0.190(3) Uani 0.808(3) 1 d PDU A 1 H14A H -0.3726 0.2294 0.8031 0.285 Uiso 0.808(3) 1 calc PR A 1 H14B H -0.2618 0.1620 0.8516 0.285 Uiso 0.808(3) 1 calc PR A 1 H14C H -0.3453 0.1660 0.6986 0.285 Uiso 0.808(3) 1 calc PR A 1 C15 C -0.0747(6) 0.2744(4) 0.8614(6) 0.156(3) Uani 0.808(3) 1 d PDU A 1 H15A H -0.0394 0.2341 0.9251 0.235 Uiso 0.808(3) 1 calc PR A 1 H15B H -0.1287 0.3113 0.9048 0.235 Uiso 0.808(3) 1 calc PR A 1 H15C H 0.0088 0.2989 0.8330 0.235 Uiso 0.808(3) 1 calc PR A 1 C1D C -0.126(2) 0.1425(11) 0.300(2) 0.107(7) Uani 0.192(3) 1 d PDU A 2 H1D H -0.1707 0.1834 0.3365 0.128 Uiso 0.192(3) 1 calc PR A 2 C2D C -0.160(3) 0.1281(13) 0.1600(19) 0.117(7) Uani 0.192(3) 1 d PDU A 2 H2D H -0.2273 0.1591 0.1027 0.140 Uiso 0.192(3) 1 calc PR A 2 C3D C -0.092(3) 0.0667(13) 0.1062(17) 0.123(7) Uani 0.192(3) 1 d PDU A 2 H3D H -0.1146 0.0566 0.0126 0.148 Uiso 0.192(3) 1 calc PR A 2 C4D C 0.008(3) 0.0205(11) 0.1921(19) 0.098(6) Uani 0.192(3) 1 d PDU A 2 H4D H 0.0528 -0.0204 0.1553 0.118 Uiso 0.192(3) 1 calc PR A 2 C4E C 0.043(2) 0.0346(9) 0.3323(17) 0.081(4) Uani 0.192(3) 1 d PDU A 2 C5D C 0.3618(17) -0.0020(9) 0.5935(18) 0.110(5) Uani 0.192(3) 1 d PDU A 2 H5D H 0.4048 -0.0430 0.5552 0.132 Uiso 0.192(3) 1 calc PR A 2 C6D C 0.4451(16) 0.0360(11) 0.7049(19) 0.116(6) Uani 0.192(3) 1 d PDU A 2 H6D H 0.5423 0.0205 0.7401 0.140 Uiso 0.192(3) 1 calc PR A 2 C7D C 0.3825(19) 0.0982(10) 0.7646(17) 0.119(6) Uani 0.192(3) 1 d PDU A 2 H7D H 0.4368 0.1242 0.8393 0.142 Uiso 0.192(3) 1 calc PR A 2 C8D C 0.2370(19) 0.1195(9) 0.7087(17) 0.101(6) Uani 0.192(3) 1 d PDU A 2 H8D H 0.1944 0.1606 0.7470 0.121 Uiso 0.192(3) 1 calc PR A 2 C8E C 0.1535(14) 0.0816(9) 0.5977(15) 0.094(4) Uani 0.192(3) 1 d PDU A 2 C9D C -0.0133(13) 0.0964(6) 0.5405(12) 0.101(4) Uani 0.192(3) 1 d PDU . 2 C9E C -0.025(2) 0.0962(10) 0.3850(12) 0.085(4) Uani 0.192(3) 1 d PDU A 2 C10D C 0.1220(15) -0.0279(6) 0.4228(13) 0.102(4) Uani 0.192(3) 1 d PDU . 2 H10B H 0.1920 -0.0518 0.3715 0.122 Uiso 0.192(3) 1 calc PR A 2 C10E C 0.2158(16) 0.0191(8) 0.5371(15) 0.092(4) Uani 0.192(3) 1 d PDU A 2 C11D C -0.038(3) 0.1820(6) 0.5815(16) 0.094(5) Uani 0.192(3) 1 d PDU A 2 O1D O -0.0193(17) 0.2465(7) 0.5356(12) 0.109(5) Uani 0.192(3) 1 d PDU A 2 O2D O -0.095(4) 0.1731(13) 0.695(2) 0.074(4) Uani 0.192(3) 1 d PDU A 2 C12D C -0.1544(19) 0.2392(9) 0.7639(14) 0.056(4) Uani 0.192(3) 1 d PDU A 2 C13D C -0.2951(14) 0.2527(7) 0.6594(12) 0.065(3) Uani 0.192(3) 1 d PDU A 2 H13D H -0.3388 0.2043 0.6282 0.097 Uiso 0.192(3) 1 calc PR A 2 H13E H -0.2713 0.2806 0.5828 0.097 Uiso 0.192(3) 1 calc PR A 2 H13F H -0.3646 0.2816 0.7006 0.097 Uiso 0.192(3) 1 calc PR A 2 C14D C -0.0644(17) 0.3111(6) 0.8018(14) 0.065(3) Uani 0.192(3) 1 d PDU A 2 H14D H -0.0591 0.3397 0.7202 0.098 Uiso 0.192(3) 1 calc PR A 2 H14E H 0.0346 0.2976 0.8472 0.098 Uiso 0.192(3) 1 calc PR A 2 H14F H -0.1113 0.3417 0.8622 0.098 Uiso 0.192(3) 1 calc PR A 2 C15D C -0.1833(10) 0.1949(5) 0.8867(9) 0.044(2) Uani 0.192(3) 1 d PDU A 2 H15D H -0.2252 0.1459 0.8575 0.067 Uiso 0.192(3) 1 calc PR A 2 H15E H -0.2520 0.2228 0.9307 0.067 Uiso 0.192(3) 1 calc PR A 2 H15F H -0.0911 0.1878 0.9502 0.067 Uiso 0.192(3) 1 calc PR A 2 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 0.085(3) 0.060(2) 0.097(3) 0.0067(19) 0.037(2) -0.0030(18) C2 0.095(3) 0.092(3) 0.091(3) 0.015(3) 0.019(2) -0.006(2) C3 0.122(3) 0.083(3) 0.084(3) -0.001(2) 0.025(3) -0.018(3) C4 0.112(3) 0.060(2) 0.086(3) -0.008(2) 0.038(2) -0.0120(19) C4A 0.079(2) 0.0464(16) 0.083(2) -0.0054(16) 0.0392(17) -0.0129(16) C5 0.077(2) 0.061(2) 0.116(3) -0.003(2) 0.035(2) 0.0040(18) C6 0.077(2) 0.086(2) 0.120(3) 0.009(2) 0.016(2) 0.0009(18) C7 0.088(2) 0.092(2) 0.098(3) -0.012(2) 0.018(2) -0.0116(19) C8 0.078(2) 0.067(2) 0.094(3) -0.0135(19) 0.026(2) -0.0086(17) C8A 0.0645(19) 0.0458(16) 0.083(2) -0.0087(16) 0.0354(17) -0.0121(14) C9 0.0625(16) 0.0376(12) 0.0818(18) -0.0022(12) 0.0383(14) -0.0081(11) C9A 0.067(2) 0.0462(16) 0.084(2) 0.0003(15) 0.0350(16) -0.0079(14) C10 0.081(2) 0.0420(14) 0.090(2) -0.0082(15) 0.0451(17) -0.0006(13) C10A 0.062(2) 0.0477(16) 0.094(2) -0.0013(15) 0.0371(16) -0.0032(14) C11 0.071(2) 0.0412(15) 0.101(3) -0.0143(17) 0.0388(19) -0.0069(13) O1 0.168(4) 0.0542(15) 0.295(6) -0.030(2) 0.159(4) -0.0205(17) O2 0.120(2) 0.048(2) 0.124(4) -0.0087(19) 0.077(3) -0.0036(18) C12 0.093(4) 0.062(3) 0.096(3) -0.018(2) 0.048(3) 0.002(2) C13 0.146(4) 0.130(4) 0.127(3) -0.004(3) 0.035(3) 0.065(3) C14 0.192(5) 0.118(4) 0.317(9) -0.045(4) 0.193(6) -0.029(4) C15 0.143(4) 0.189(7) 0.128(4) -0.071(4) 0.001(4) 0.054(4) C1D 0.122(15) 0.103(13) 0.104(10) 0.007(10) 0.042(12) 0.017(10) C2D 0.137(14) 0.104(12) 0.108(11) -0.003(11) 0.018(11) 0.004(10) C3D 0.160(14) 0.097(13) 0.114(12) -0.008(10) 0.030(11) -0.001(10) C4D 0.134(16) 0.077(11) 0.095(9) -0.014(8) 0.052(11) -0.011(9) C4E 0.113(11) 0.064(8) 0.087(8) -0.005(7) 0.071(7) -0.008(8) C5D 0.101(9) 0.097(11) 0.144(14) -0.010(10) 0.057(8) -0.001(9) C6D 0.092(10) 0.098(13) 0.166(15) -0.007(12) 0.039(9) 0.010(9) C7D 0.112(9) 0.114(11) 0.138(13) -0.021(11) 0.041(9) -0.005(9) C8D 0.113(10) 0.077(11) 0.124(16) -0.016(10) 0.052(9) 0.009(9) C8E 0.114(8) 0.090(9) 0.091(8) -0.001(7) 0.056(6) 0.000(7) C9D 0.127(8) 0.098(7) 0.091(7) -0.011(7) 0.053(7) 0.023(8) C9E 0.117(12) 0.065(8) 0.088(7) 0.010(6) 0.060(7) -0.001(8) C10D 0.118(10) 0.088(8) 0.112(9) -0.008(6) 0.054(7) 0.016(7) C10E 0.100(9) 0.075(9) 0.116(10) -0.006(7) 0.059(7) 0.000(7) C11D 0.151(13) 0.084(7) 0.059(8) 0.010(6) 0.049(9) 0.021(8) O1D 0.160(13) 0.107(8) 0.080(7) 0.054(7) 0.078(8) 0.046(9) O2D 0.127(12) 0.036(6) 0.072(7) 0.007(5) 0.050(6) 0.028(7) C12D 0.061(9) 0.050(8) 0.059(8) -0.006(6) 0.018(6) 0.008(6) C13D 0.069(7) 0.050(7) 0.074(7) 0.011(6) 0.008(6) 0.012(5) C14D 0.089(8) 0.039(5) 0.070(9) -0.003(5) 0.022(7) 0.004(5) C15D 0.033(5) 0.059(5) 0.043(5) -0.013(4) 0.010(4) -0.013(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 C2 1.344(6) . ? C1 C9A 1.426(5) . ? C1 H1A 0.9300 . ? C2 C3 1.419(7) . ? C2 H2A 0.9300 . ? C3 C4 1.338(6) . ? C3 H3A 0.9300 . ? C4 C4A 1.417(6) . ? C4 H4A 0.9300 . ? C4A C10 1.363(5) . ? C4A C9A 1.446(4) . ? C5 C6 1.344(6) . ? C5 C10A 1.425(5) . ? C5 H5A 0.9300 . ? C6 C7 1.424(5) . ? C6 H6A 0.9300 . ? C7 C8 1.347(5) . ? C7 H7A 0.9300 . ? C8 C8A 1.428(5) . ? C8 H8A 0.9300 . ? C8A C9 1.406(4) . ? C8A C10A 1.443(4) . ? C9 C9A 1.384(4) . ? C9 C11 1.506(4) . ? C10 C10A 1.391(5) . ? C10 H10A 0.9300 . ? C11 O1 1.172(4) . ? C11 O2 1.308(5) . ? O2 C12 1.492(4) . ? C12 C15 1.473(6) . ? C12 C14 1.500(5) . ? C12 C13 1.510(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C1D C9E 1.386(9) . ? C1D C2D 1.386(9) . ? C1D H1D 0.9300 . ? C2D C3D 1.390(9) . ? C2D H2D 0.9300 . ? C3D C4D 1.387(9) . ? C3D H3D 0.9300 . ? C4D C4E 1.389(9) . ? C4D H4D 0.9300 . ? C4E C9E 1.390(9) . ? C4E C10D 1.510(9) . ? C5D C6D 1.388(9) . ? C5D C10E 1.394(9) . ? C5D H5D 0.9300 . ? C6D C7D 1.406(9) . ? C6D H6D 0.9300 . ? C7D C8D 1.390(9) . ? C7D H7D 0.9300 . ? C8D C8E 1.385(9) . ? C8D H8D 0.9300 . ? C8E C10E 1.415(9) . ? C8E C9D 1.542(9) . ? C9D C9E 1.525(9) . ? C9D C11D 1.576(9) . ? C9D C10D 1.637(7) 3_556 ? C10D C10E 1.526(9) . ? C10D C9D 1.637(7) 3_556 ? C10D H10B 0.9800 . ? C11D O1D 1.237(9) . ? C11D O2D 1.336(9) . ? O2D C12D 1.492(10) . ? C12D C15D 1.506(10) . ? C12D C14D 1.508(9) . ? C12D C13D 1.510(9) . ? C13D H13D 0.9600 . ? C13D H13E 0.9600 . ? C13D H13F 0.9600 . ? C14D H14D 0.9600 . ? C14D H14E 0.9600 . ? C14D H14F 0.9600 . ? C15D H15D 0.9600 . ? C15D H15E 0.9600 . ? C15D H15F 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 C2 C1 C9A 122.2(4) . . ? C2 C1 H1A 118.9 . . ? C9A C1 H1A 118.9 . . ? C1 C2 C3 120.0(4) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.0(4) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C4A 122.7(4) . . ? C3 C4 H4A 118.7 . . ? C4A C4 H4A 118.7 . . ? C10 C4A C4 122.6(4) . . ? C10 C4A C9A 119.8(3) . . ? C4 C4A C9A 117.6(4) . . ? C6 C5 C10A 121.6(3) . . ? C6 C5 H5A 119.2 . . ? C10A C5 H5A 119.2 . . ? C5 C6 C7 120.0(4) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C8A 121.7(4) . . ? C7 C8 H8A 119.2 . . ? C8A C8 H8A 119.2 . . ? C9 C8A C8 123.9(3) . . ? C9 C8A C10A 118.7(3) . . ? C8 C8A C10A 117.4(3) . . ? C9A C9 C8A 121.7(3) . . ? C9A C9 C11 119.7(3) . . ? C8A C9 C11 118.6(3) . . ? C9 C9A C1 123.9(3) . . ? C9 C9A C4A 118.7(3) . . ? C1 C9A C4A 117.4(3) . . ? C4A C10 C10A 122.4(3) . . ? C4A C10 H10A 118.8 . . ? C10A C10 H10A 118.8 . . ? C10 C10A C5 122.6(3) . . ? C10 C10A C8A 118.7(3) . . ? C5 C10A C8A 118.7(3) . . ? O1 C11 O2 123.6(4) . . ? O1 C11 C9 124.6(3) . . ? O2 C11 C9 111.7(3) . . ? C11 O2 C12 124.1(5) . . ? C15 C12 O2 107.2(5) . . ? C15 C12 C14 113.2(4) . . ? O2 C12 C14 105.0(4) . . ? C15 C12 C13 111.0(4) . . ? O2 C12 C13 111.8(5) . . ? C14 C12 C13 108.6(4) . . ? C9E C1D C2D 120.2(9) . . ? C9E C1D H1D 119.9 . . ? C2D C1D H1D 119.9 . . ? C1D C2D C3D 119.4(9) . . ? C1D C2D H2D 120.3 . . ? C3D C2D H2D 120.3 . . ? C4D C3D C2D 120.1(9) . . ? C4D C3D H3D 119.9 . . ? C2D C3D H3D 119.9 . . ? C3D C4D C4E 120.8(9) . . ? C3D C4D H4D 119.6 . . ? C4E C4D H4D 119.6 . . ? C4D C4E C9E 118.7(8) . . ? C4D C4E C10D 117.5(14) . . ? C9E C4E C10D 122.2(14) . . ? C6D C5D C10E 122.3(9) . . ? C6D C5D H5D 118.9 . . ? C10E C5D H5D 118.9 . . ? C5D C6D C7D 119.9(9) . . ? C5D C6D H6D 120.1 . . ? C7D C6D H6D 120.1 . . ? C8D C7D C6D 118.1(9) . . ? C8D C7D H7D 120.9 . . ? C6D C7D H7D 120.9 . . ? C8E C8D C7D 122.1(9) . . ? C8E C8D H8D 118.9 . . ? C7D C8D H8D 118.9 . . ? C8D C8E C10E 120.1(8) . . ? C8D C8E C9D 124.8(11) . . ? C10E C8E C9D 114.8(11) . . ? C9E C9D C8E 104.6(11) . . ? C9E C9D C11D 106.0(11) . . ? C8E C9D C11D 104.0(13) . . ? C9E C9D C10D 106.9(11) . 3_556 ? C8E C9D C10D 113.1(11) . 3_556 ? C11D C9D C10D 120.9(10) . 3_556 ? C1D C9E C4E 120.8(8) . . ? C1D C9E C9D 122.0(13) . . ? C4E C9E C9D 115.4(13) . . ? C4E C10D C10E 101.2(12) . . ? C4E C10D C9D 114.6(11) . 3_556 ? C10E C10D C9D 120.4(11) . 3_556 ? C4E C10D H10B 106.6 . . ? C10E C10D H10B 106.6 . . ? C9D C10D H10B 106.6 3_556 . ? C5D C10E C8E 117.5(8) . . ? C5D C10E C10D 121.2(12) . . ? C8E C10E C10D 121.1(12) . . ? O1D C11D O2D 121.2(14) . . ? O1D C11D C9D 137.1(13) . . ? O2D C11D C9D 101.7(12) . . ? C11D O2D C12D 121.9(17) . . ? O2D C12D C15D 96.1(10) . . ? O2D C12D C14D 122.1(18) . . ? C15D C12D C14D 113.2(10) . . ? O2D C12D C13D 97.9(16) . . ? C15D C12D C13D 112.4(10) . . ? C14D C12D C13D 113.3(11) . . ? C12D C13D H13D 109.5 . . ? C12D C13D H13E 109.5 . . ? H13D C13D H13E 109.5 . . ? C12D C13D H13F 109.5 . . ? H13D C13D H13F 109.5 . . ? H13E C13D H13F 109.5 . . ? C12D C14D H14D 109.5 . . ? C12D C14D H14E 109.5 . . ? H14D C14D H14E 109.5 . . ? C12D C14D H14F 109.5 . . ? H14D C14D H14F 109.5 . . ? H14E C14D H14F 109.5 . . ? C12D C15D H15D 109.5 . . ? C12D C15D H15E 109.5 . . ? H15D C15D H15E 109.5 . . ? C12D C15D H15F 109.5 . . ? H15D C15D H15F 109.5 . . ? H15E C15D H15F 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 C9A C1 C2 C3 0.8(7) . . . . ? C1 C2 C3 C4 -1.0(7) . . . . ? C2 C3 C4 C4A 0.0(7) . . . . ? C3 C4 C4A C10 179.9(5) . . . . ? C3 C4 C4A C9A 1.0(6) . . . . ? C10A C5 C6 C7 0.2(6) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C6 C7 C8 C8A -0.5(6) . . . . ? C7 C8 C8A C9 179.4(3) . . . . ? C7 C8 C8A C10A 0.5(6) . . . . ? C8 C8A C9 C9A 179.8(3) . . . . ? C10A C8A C9 C9A -1.2(4) . . . . ? C8 C8A C9 C11 1.4(5) . . . . ? C10A C8A C9 C11 -179.7(3) . . . . ? C8A C9 C9A C1 -179.1(3) . . . . ? C11 C9 C9A C1 -0.6(4) . . . . ? C8A C9 C9A C4A 1.5(4) . . . . ? C11 C9 C9A C4A 179.9(3) . . . . ? C2 C1 C9A C9 -179.2(4) . . . . ? C2 C1 C9A C4A 0.2(5) . . . . ? C10 C4A C9A C9 -0.5(5) . . . . ? C4 C4A C9A C9 178.4(4) . . . . ? C10 C4A C9A C1 180.0(4) . . . . ? C4 C4A C9A C1 -1.1(5) . . . . ? C4 C4A C10 C10A -179.5(4) . . . . ? C9A C4A C10 C10A -0.7(5) . . . . ? C4A C10 C10A C5 -179.9(4) . . . . ? C4A C10 C10A C8A 0.9(5) . . . . ? C6 C5 C10A C10 -179.3(3) . . . . ? C6 C5 C10A C8A -0.2(5) . . . . ? C9 C8A C10A C10 0.0(4) . . . . ? C8 C8A C10A C10 179.0(3) . . . . ? C9 C8A C10A C5 -179.2(3) . . . . ? C8 C8A C10A C5 -0.2(5) . . . . ? C9A C9 C11 O1 -91.8(5) . . . . ? C8A C9 C11 O1 86.6(5) . . . . ? C9A C9 C11 O2 88.6(6) . . . . ? C8A C9 C11 O2 -92.9(5) . . . . ? O1 C11 O2 C12 1.5(11) . . . . ? C9 C11 O2 C12 -179.0(6) . . . . ? C11 O2 C12 C15 -69.6(9) . . . . ? C11 O2 C12 C14 169.7(7) . . . . ? C11 O2 C12 C13 52.2(9) . . . . ? C9E C1D C2D C3D 0.1(3) . . . . ? C1D C2D C3D C4D 0.0(3) . . . . ? C2D C3D C4D C4E 0.1(6) . . . . ? C3D C4D C4E C9E -0.2(8) . . . . ? C3D C4D C4E C10D 165.5(16) . . . . ? C10E C5D C6D C7D 0.0(3) . . . . ? C5D C6D C7D C8D -0.1(3) . . . . ? C6D C7D C8D C8E 0.2(6) . . . . ? C7D C8D C8E C10E -0.3(8) . . . . ? C7D C8D C8E C9D 173.0(15) . . . . ? C8D C8E C9D C9E 137.5(12) . . . . ? C10E C8E C9D C9E -48.9(14) . . . . ? C8D C8E C9D C11D 26.5(15) . . . . ? C10E C8E C9D C11D -159.9(10) . . . . ? C8D C8E C9D C10D -106.5(13) . . . 3_556 ? C10E C8E C9D C10D 67.1(13) . . . 3_556 ? C2D C1D C9E C4E -0.2(6) . . . . ? C2D C1D C9E C9D -164.2(16) . . . . ? C4D C4E C9E C1D 0.3(8) . . . . ? C10D C4E C9E C1D -164.8(17) . . . . ? C4D C4E C9E C9D 165.3(15) . . . . ? C10D C4E C9E C9D 0(2) . . . . ? C8E C9D C9E C1D -146.4(12) . . . . ? C11D C9D C9E C1D -36.9(17) . . . . ? C10D C9D C9E C1D 93.4(13) 3_556 . . . ? C8E C9D C9E C4E 48.8(16) . . . . ? C11D C9D C9E C4E 158.3(14) . . . . ? C10D C9D C9E C4E -71.4(14) 3_556 . . . ? C4D C4E C10D C10E 148.3(12) . . . . ? C9E C4E C10D C10E -46.5(18) . . . . ? C4D C4E C10D C9D -80.5(15) . . . 3_556 ? C9E C4E C10D C9D 84.7(17) . . . 3_556 ? C6D C5D C10E C8E -0.1(6) . . . . ? C6D C5D C10E C10D -174.6(14) . . . . ? C8D C8E C10E C5D 0.2(8) . . . . ? C9D C8E C10E C5D -173.8(13) . . . . ? C8D C8E C10E C10D 174.7(14) . . . . ? C9D C8E C10E C10D 0.8(16) . . . . ? C4E C10D C10E C5D -140.4(12) . . . . ? C9D C10D C10E C5D 92.2(14) 3_556 . . . ? C4E C10D C10E C8E 45.3(15) . . . . ? C9D C10D C10E C8E -82.1(15) 3_556 . . . ? C9E C9D C11D O1D -27(3) . . . . ? C8E C9D C11D O1D 83(3) . . . . ? C10D C9D C11D O1D -149(3) 3_556 . . . ? C9E C9D C11D O2D 152(2) . . . . ? C8E C9D C11D O2D -98(2) . . . . ? C10D C9D C11D O2D 30(2) 3_556 . . . ? O1D C11D O2D C12D 6(4) . . . . ? C9D C11D O2D C12D -173(2) . . . . ? C11D O2D C12D C15D -174(3) . . . . ? C11D O2D C12D C14D -51(4) . . . . ? C11D O2D C12D C13D 73(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.033 # Attachment 'cb14_new_0m.cif' data_cb14_new_0m _database_code_depnum_ccdc_archive 'CCDC 808562' #TrackingRef 'cb14_new_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 O2' _chemical_formula_weight 278.33 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1419(7) _cell_length_b 17.5398(14) _cell_length_c 9.7526(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.8192(13) _cell_angle_gamma 90.00 _cell_volume 1540.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6170 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 29.48 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 22802 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4329 _reflns_number_gt 2775 _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^)+(0.0558P)^2^+0.1256P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4329 _refine_ls_number_parameters 260 _refine_ls_number_restraints 230 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.006 _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 0.40852(13) 0.14473(7) -0.16151(14) 0.0674(3) Uani 1 1 d . . . H1 H 0.3650 0.1874 -0.1286 0.081 Uiso 1 1 calc R . . C2 C 0.35305(16) 0.11722(8) -0.28917(15) 0.0795(4) Uani 1 1 d . . . H2 H 0.2724 0.1412 -0.3430 0.095 Uiso 1 1 calc R . . C3 C 0.41638(17) 0.05241(8) -0.34150(14) 0.0814(4) Uani 1 1 d . . . H3 H 0.3767 0.0338 -0.4293 0.098 Uiso 1 1 calc R . . C4 C 0.53333(16) 0.01741(7) -0.26573(13) 0.0711(3) Uani 1 1 d . . . H4 H 0.5734 -0.0253 -0.3019 0.085 Uiso 1 1 calc R . . C4A C 0.59746(12) 0.04421(5) -0.13132(11) 0.0561(3) Uani 1 1 d . . . C5 C 0.90753(14) -0.00020(7) 0.16049(15) 0.0744(3) Uani 1 1 d . A . H5 H 0.9499 -0.0424 0.1249 0.089 Uiso 1 1 calc R . . C6 C 0.96614(16) 0.02589(9) 0.28757(18) 0.0870(4) Uani 1 1 d . . . H6 H 1.0481 0.0016 0.3389 0.104 Uiso 1 1 calc R . . C7 C 0.90353(16) 0.09007(9) 0.34356(16) 0.0855(4) Uani 1 1 d . . . H7 H 0.9449 0.1079 0.4315 0.103 Uiso 1 1 calc R . . C8 C 0.78453(14) 0.12567(7) 0.27082(13) 0.0715(3) Uani 1 1 d . . . H8 H 0.7450 0.1677 0.3098 0.086 Uiso 1 1 calc R . . C8A C 0.71795(11) 0.10064(6) 0.13607(11) 0.0555(3) Uani 1 1 d . A . C9 C 0.59369(11) 0.13563(5) 0.05666(11) 0.0533(3) Uani 1 1 d D . . C9A C 0.53237(11) 0.10972(5) -0.07642(11) 0.0536(3) Uani 1 1 d . A . C10 C 0.71898(12) 0.00920(6) -0.05143(12) 0.0600(3) Uani 1 1 d . A . H10 H 0.7598 -0.0335 -0.0870 0.072 Uiso 1 1 calc R . . C10A C 0.78181(12) 0.03546(6) 0.07916(12) 0.0579(3) Uani 1 1 d . . . C11 C 0.5259(5) 0.20355(13) 0.1190(5) 0.0611(14) Uani 0.691(4) 1 d PDU A 1 O1 O 0.5772(4) 0.26632(18) 0.1237(4) 0.1210(14) Uani 0.691(4) 1 d PDU A 1 O2 O 0.4108(6) 0.1850(3) 0.1755(6) 0.0588(11) Uani 0.691(4) 1 d PDU A 1 C12 C 0.3249(5) 0.2401(2) 0.2470(4) 0.0558(9) Uani 0.691(4) 1 d PDU A 1 C13 C 0.2731(4) 0.30577(15) 0.1520(3) 0.0857(8) Uani 0.691(4) 1 d PDU A 1 H13A H 0.3561 0.3377 0.1427 0.128 Uiso 0.691(4) 1 calc PR A 1 H13B H 0.2009 0.3349 0.1904 0.128 Uiso 0.691(4) 1 calc PR A 1 H13C H 0.2291 0.2866 0.0621 0.128 Uiso 0.691(4) 1 calc PR A 1 C14 C 0.1969(3) 0.19202(12) 0.2744(4) 0.0924(10) Uani 0.691(4) 1 d PDU A 1 H14A H 0.2339 0.1480 0.3276 0.139 Uiso 0.691(4) 1 calc PR A 1 H14B H 0.1392 0.1761 0.1875 0.139 Uiso 0.691(4) 1 calc PR A 1 H14C H 0.1356 0.2213 0.3255 0.139 Uiso 0.691(4) 1 calc PR A 1 C15 C 0.4226(3) 0.2646(2) 0.3793(3) 0.0942(9) Uani 0.691(4) 1 d PDU A 1 H15A H 0.4570 0.2205 0.4336 0.141 Uiso 0.691(4) 1 calc PR A 1 H15B H 0.3671 0.2967 0.4315 0.141 Uiso 0.691(4) 1 calc PR A 1 H15C H 0.5062 0.2924 0.3574 0.141 Uiso 0.691(4) 1 calc PR A 1 C11D C 0.5243(11) 0.2025(3) 0.1093(10) 0.062(3) Uani 0.309(4) 1 d PDU A 2 O1D O 0.5287(10) 0.2653(3) 0.0639(7) 0.095(2) Uani 0.309(4) 1 d PDU A 2 O2D O 0.4408(14) 0.1803(7) 0.1988(14) 0.061(2) Uani 0.309(4) 1 d PDU A 2 C12D C 0.3559(10) 0.2375(5) 0.2650(8) 0.056(2) Uani 0.309(4) 1 d PDU A 2 C13D C 0.2239(7) 0.2619(5) 0.1590(6) 0.102(2) Uani 0.309(4) 1 d PDU A 2 H13D H 0.1672 0.2178 0.1243 0.153 Uiso 0.309(4) 1 calc PR A 2 H13E H 0.2579 0.2876 0.0834 0.153 Uiso 0.309(4) 1 calc PR A 2 H13F H 0.1627 0.2958 0.2019 0.153 Uiso 0.309(4) 1 calc PR A 2 C14D C 0.3068(8) 0.1916(3) 0.3807(7) 0.099(2) Uani 0.309(4) 1 d PDU A 2 H14D H 0.2472 0.1494 0.3414 0.148 Uiso 0.309(4) 1 calc PR A 2 H14E H 0.2496 0.2235 0.4316 0.148 Uiso 0.309(4) 1 calc PR A 2 H14F H 0.3926 0.1729 0.4423 0.148 Uiso 0.309(4) 1 calc PR A 2 C15D C 0.4444(6) 0.3062(3) 0.3249(7) 0.0843(16) Uani 0.309(4) 1 d PDU A 2 H15D H 0.5359 0.2897 0.3803 0.126 Uiso 0.309(4) 1 calc PR A 2 H15E H 0.3880 0.3346 0.3821 0.126 Uiso 0.309(4) 1 calc PR A 2 H15F H 0.4653 0.3380 0.2505 0.126 Uiso 0.309(4) 1 calc PR A 2 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 0.0701(7) 0.0575(6) 0.0805(8) 0.0070(6) 0.0297(6) 0.0045(5) C2 0.0791(8) 0.0833(9) 0.0770(9) 0.0136(7) 0.0160(7) 0.0011(7) C3 0.0990(10) 0.0820(9) 0.0656(8) -0.0017(7) 0.0210(7) -0.0116(8) C4 0.0938(9) 0.0577(6) 0.0687(8) -0.0051(5) 0.0331(7) -0.0059(6) C4A 0.0685(6) 0.0442(5) 0.0634(6) -0.0008(4) 0.0336(5) -0.0053(4) C5 0.0671(7) 0.0669(7) 0.0949(10) 0.0043(7) 0.0301(7) 0.0104(6) C6 0.0676(8) 0.0941(10) 0.0987(11) 0.0089(8) 0.0123(8) 0.0034(7) C7 0.0771(9) 0.0966(10) 0.0829(9) -0.0097(8) 0.0141(7) -0.0110(8) C8 0.0707(8) 0.0695(7) 0.0787(8) -0.0128(6) 0.0254(6) -0.0073(6) C8A 0.0577(6) 0.0490(5) 0.0670(6) -0.0035(4) 0.0309(5) -0.0060(4) C9 0.0574(6) 0.0409(4) 0.0700(7) -0.0032(4) 0.0350(5) -0.0036(4) C9A 0.0591(6) 0.0424(5) 0.0664(6) 0.0022(4) 0.0312(5) -0.0036(4) C10 0.0695(7) 0.0440(5) 0.0754(7) -0.0035(5) 0.0375(6) 0.0040(4) C10A 0.0583(6) 0.0502(5) 0.0724(7) 0.0017(5) 0.0317(5) 0.0006(4) C11 0.066(3) 0.0368(13) 0.091(3) -0.0159(14) 0.043(2) 0.0013(14) O1 0.114(2) 0.0572(12) 0.220(4) -0.0455(18) 0.109(2) -0.0338(13) O2 0.0631(16) 0.0406(12) 0.082(2) -0.0066(12) 0.0398(16) -0.0003(12) C12 0.0560(17) 0.0555(14) 0.0616(16) -0.0116(11) 0.0260(12) 0.0108(11) C13 0.0999(18) 0.0722(14) 0.0910(15) 0.0051(12) 0.0339(13) 0.0312(13) C14 0.0831(16) 0.0802(13) 0.132(2) -0.0129(13) 0.0691(17) -0.0007(11) C15 0.0976(17) 0.114(2) 0.0717(15) -0.0282(15) 0.0168(13) 0.0173(16) C11D 0.058(5) 0.076(5) 0.053(4) 0.017(3) 0.016(3) -0.023(3) O1D 0.158(7) 0.037(2) 0.115(4) 0.024(2) 0.096(4) 0.021(3) O2D 0.082(5) 0.047(2) 0.066(3) 0.0095(19) 0.047(4) 0.021(3) C12D 0.051(3) 0.049(3) 0.071(4) 0.008(2) 0.024(2) 0.013(2) C13D 0.085(4) 0.132(6) 0.088(4) -0.020(4) 0.013(3) 0.048(4) C14D 0.125(5) 0.090(3) 0.102(4) 0.001(3) 0.079(4) 0.016(3) C15D 0.106(4) 0.070(3) 0.082(4) -0.028(3) 0.032(3) 0.001(3) _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 C2 1.3507(18) . ? C1 C9A 1.4238(16) . ? C1 H1 0.9300 . ? C2 C3 1.410(2) . ? C2 H2 0.9300 . ? C3 C4 1.3404(19) . ? C3 H3 0.9300 . ? C4 C4A 1.4215(16) . ? C4 H4 0.9300 . ? C4A C10 1.3867(16) . ? C4A C9A 1.4387(13) . ? C5 C6 1.3439(19) . ? C5 C10A 1.4249(16) . ? C5 H5 0.9300 . ? C6 C7 1.414(2) . ? C6 H6 0.9300 . ? C7 C8 1.3467(19) . ? C7 H7 0.9300 . ? C8 C8A 1.4204(16) . ? C8 H8 0.9300 . ? C8A C9 1.4024(15) . ? C8A C10A 1.4376(14) . ? C9 C9A 1.3989(15) . ? C9 C11D 1.467(6) . ? C9 C11 1.517(2) . ? C10 C10A 1.3837(16) . ? C10 H10 0.9300 . ? C11 O1 1.194(4) . ? C11 O2 1.309(3) . ? O2 C12 1.490(3) . ? C12 C15 1.502(4) . ? C12 C14 1.503(4) . ? C12 C13 1.504(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C11D O1D 1.190(6) . ? C11D O2D 1.313(7) . ? O2D C12D 1.482(7) . ? C12D C13D 1.511(7) . ? C12D C15D 1.513(7) . ? C12D C14D 1.514(7) . ? C13D H13D 0.9600 . ? C13D H13E 0.9600 . ? C13D H13F 0.9600 . ? C14D H14D 0.9600 . ? C14D H14E 0.9600 . ? C14D H14F 0.9600 . ? C15D H15D 0.9600 . ? C15D H15E 0.9600 . ? C15D H15F 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 C2 C1 C9A 121.29(11) . . ? C2 C1 H1 119.4 . . ? C9A C1 H1 119.4 . . ? C1 C2 C3 120.58(13) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.51(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 121.45(12) . . ? C3 C4 H4 119.3 . . ? C4A C4 H4 119.3 . . ? C10 C4A C4 122.45(10) . . ? C10 C4A C9A 119.15(10) . . ? C4 C4A C9A 118.39(11) . . ? C6 C5 C10A 121.38(12) . . ? C6 C5 H5 119.3 . . ? C10A C5 H5 119.3 . . ? C5 C6 C7 120.21(13) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.64(14) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 121.62(12) . . ? C7 C8 H8 119.2 . . ? C8A C8 H8 119.2 . . ? C9 C8A C8 123.69(10) . . ? C9 C8A C10A 118.61(10) . . ? C8 C8A C10A 117.70(11) . . ? C9A C9 C8A 121.93(9) . . ? C9A C9 C11D 117.1(5) . . ? C8A C9 C11D 121.0(5) . . ? C9A C9 C11 120.0(2) . . ? C8A C9 C11 118.0(2) . . ? C11D C9 C11 3.1(6) . . ? C9 C9A C1 123.62(9) . . ? C9 C9A C4A 118.62(10) . . ? C1 C9A C4A 117.76(10) . . ? C10A C10 C4A 122.47(9) . . ? C10A C10 H10 118.8 . . ? C4A C10 H10 118.8 . . ? C10 C10A C5 122.35(10) . . ? C10 C10A C8A 119.20(10) . . ? C5 C10A C8A 118.44(11) . . ? O1 C11 O2 123.4(3) . . ? O1 C11 C9 123.7(3) . . ? O2 C11 C9 112.7(3) . . ? C11 O2 C12 124.2(4) . . ? O2 C12 C15 107.7(4) . . ? O2 C12 C14 102.0(3) . . ? C15 C12 C14 112.0(3) . . ? O2 C12 C13 110.1(3) . . ? C15 C12 C13 112.8(3) . . ? C14 C12 C13 111.5(3) . . ? O1D C11D O2D 125.6(8) . . ? O1D C11D C9 124.5(6) . . ? O2D C11D C9 109.3(6) . . ? C11D O2D C12D 119.8(9) . . ? O2D C12D C13D 108.1(8) . . ? O2D C12D C15D 115.0(8) . . ? C13D C12D C15D 110.5(6) . . ? O2D C12D C14D 102.1(6) . . ? C13D C12D C14D 110.9(6) . . ? C15D C12D C14D 110.0(6) . . ? C12D C13D H13D 109.5 . . ? C12D C13D H13E 109.5 . . ? H13D C13D H13E 109.5 . . ? C12D C13D H13F 109.5 . . ? H13D C13D H13F 109.5 . . ? H13E C13D H13F 109.5 . . ? C12D C14D H14D 109.5 . . ? C12D C14D H14E 109.5 . . ? H14D C14D H14E 109.5 . . ? C12D C14D H14F 109.5 . . ? H14D C14D H14F 109.5 . . ? H14E C14D H14F 109.5 . . ? C12D C15D H15D 109.5 . . ? C12D C15D H15E 109.5 . . ? H15D C15D H15E 109.5 . . ? C12D C15D H15F 109.5 . . ? H15D C15D H15F 109.5 . . ? H15E C15D H15F 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 C9A C1 C2 C3 0.33(19) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C2 C3 C4 C4A -0.19(19) . . . . ? C3 C4 C4A C10 -179.60(11) . . . . ? C3 C4 C4A C9A 0.95(16) . . . . ? C10A C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C8A -0.2(2) . . . . ? C7 C8 C8A C9 179.72(11) . . . . ? C7 C8 C8A C10A 0.11(17) . . . . ? C8 C8A C9 C9A 179.27(9) . . . . ? C10A C8A C9 C9A -1.11(14) . . . . ? C8 C8A C9 C11D 0.7(3) . . . . ? C10A C8A C9 C11D -179.7(3) . . . . ? C8 C8A C9 C11 -0.6(2) . . . . ? C10A C8A C9 C11 179.00(16) . . . . ? C8A C9 C9A C1 -178.50(9) . . . . ? C11D C9 C9A C1 0.2(3) . . . . ? C11 C9 C9A C1 1.4(2) . . . . ? C8A C9 C9A C4A 1.38(13) . . . . ? C11D C9 C9A C4A -179.9(3) . . . . ? C11 C9 C9A C4A -178.74(16) . . . . ? C2 C1 C9A C9 -179.68(10) . . . . ? C2 C1 C9A C4A 0.44(16) . . . . ? C10 C4A C9A C9 -0.41(13) . . . . ? C4 C4A C9A C9 179.06(9) . . . . ? C10 C4A C9A C1 179.48(9) . . . . ? C4 C4A C9A C1 -1.05(14) . . . . ? C4 C4A C10 C10A 179.72(9) . . . . ? C9A C4A C10 C10A -0.84(15) . . . . ? C4A C10 C10A C5 -179.40(10) . . . . ? C4A C10 C10A C8A 1.11(15) . . . . ? C6 C5 C10A C10 -179.49(11) . . . . ? C6 C5 C10A C8A 0.01(17) . . . . ? C9 C8A C10A C10 -0.13(14) . . . . ? C8 C8A C10A C10 179.50(9) . . . . ? C9 C8A C10A C5 -179.64(9) . . . . ? C8 C8A C10A C5 -0.01(14) . . . . ? C9A C9 C11 O1 -102.0(5) . . . . ? C8A C9 C11 O1 77.9(5) . . . . ? C11D C9 C11 O1 -82(8) . . . . ? C9A C9 C11 O2 82.3(5) . . . . ? C8A C9 C11 O2 -97.8(5) . . . . ? C11D C9 C11 O2 102(9) . . . . ? O1 C11 O2 C12 2.8(10) . . . . ? C9 C11 O2 C12 178.6(4) . . . . ? C11 O2 C12 C15 -68.9(7) . . . . ? C11 O2 C12 C14 173.0(6) . . . . ? C11 O2 C12 C13 54.5(7) . . . . ? C9A C9 C11D O1D -68.5(11) . . . . ? C8A C9 C11D O1D 110.2(10) . . . . ? C11 C9 C11D O1D 131(9) . . . . ? C9A C9 C11D O2D 102.6(10) . . . . ? C8A C9 C11D O2D -78.7(11) . . . . ? C11 C9 C11D O2D -58(8) . . . . ? O1D C11D O2D C12D -8(2) . . . . ? C9 C11D O2D C12D -178.8(10) . . . . ? C11D O2D C12D C13D 75.5(14) . . . . ? C11D O2D C12D C15D -48.4(15) . . . . ? C11D O2D C12D C14D -167.5(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.176 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.022 # Attachment 'cb15_0m_TPAE.cif' data_cb15_0m _database_code_depnum_ccdc_archive 'CCDC 808563' #TrackingRef 'cb15_0m_TPAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 O2' _chemical_formula_weight 362.49 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0442(4) _cell_length_b 13.8741(5) _cell_length_c 30.5325(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.1613(7) _cell_angle_gamma 90.00 _cell_volume 4243.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9978 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.87 _exptl_crystal_description 'prism frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9695 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 46800 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 29.57 _reflns_number_total 11893 _reflns_number_gt 9266 _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^)+(0.0560P)^2^+0.9605P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11893 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.33190(11) 0.73577(8) 0.08125(4) 0.0207(2) Uani 1 1 d . . . H1A H 0.3345 0.7931 0.0983 0.025 Uiso 1 1 calc R . . C2 C 0.43917(12) 0.71145(9) 0.05858(4) 0.0254(3) Uani 1 1 d . . . H2A H 0.5154 0.7522 0.0599 0.031 Uiso 1 1 calc R . . C3 C 0.43811(12) 0.62604(9) 0.03299(4) 0.0263(3) Uani 1 1 d . . . H3A H 0.5138 0.6096 0.0176 0.032 Uiso 1 1 calc R . . C4 C 0.32910(12) 0.56756(9) 0.03042(4) 0.0233(2) Uani 1 1 d . . . H4A H 0.3295 0.5107 0.0131 0.028 Uiso 1 1 calc R . . C4A C 0.21377(11) 0.59025(8) 0.05335(3) 0.0174(2) Uani 1 1 d . . . C5 C -0.12914(11) 0.49593(8) 0.06900(4) 0.0200(2) Uani 1 1 d . . . H5A H -0.1305 0.4396 0.0513 0.024 Uiso 1 1 calc R . . C6 C -0.23869(12) 0.51926(8) 0.09052(4) 0.0229(2) Uani 1 1 d . . . H6A H -0.3157 0.4794 0.0877 0.027 Uiso 1 1 calc R . . C7 C -0.23803(11) 0.60326(8) 0.11724(4) 0.0226(2) Uani 1 1 d . . . H7A H -0.3148 0.6189 0.1323 0.027 Uiso 1 1 calc R . . C8 C -0.12866(11) 0.66148(8) 0.12156(4) 0.0191(2) Uani 1 1 d . . . H8A H -0.1298 0.7171 0.1397 0.023 Uiso 1 1 calc R . . C8A C -0.01200(10) 0.63993(7) 0.09913(3) 0.0156(2) Uani 1 1 d . . . C9 C 0.10219(10) 0.69891(7) 0.10202(3) 0.0154(2) Uani 1 1 d . . . C9A C 0.21545(10) 0.67603(8) 0.07966(3) 0.0164(2) Uani 1 1 d . . . C10 C 0.10047(11) 0.53197(8) 0.05043(4) 0.0183(2) Uani 1 1 d . . . H10A H 0.0999 0.4753 0.0329 0.022 Uiso 1 1 calc R . . C10A C -0.01227(11) 0.55480(8) 0.07259(3) 0.0163(2) Uani 1 1 d . . . C11 C 0.10209(10) 0.79007(8) 0.12849(3) 0.0170(2) Uani 1 1 d . . . O1 O 0.16882(8) 0.80261(6) 0.16239(3) 0.02557(19) Uani 1 1 d . . . O2 O 0.01867(8) 0.85364(5) 0.10806(2) 0.01809(16) Uani 1 1 d . . . C12 C -0.00065(11) 0.95352(8) 0.12481(4) 0.0194(2) Uani 1 1 d . . . C13 C 0.13298(12) 1.00653(8) 0.12844(4) 0.0239(2) Uani 1 1 d . . . H13A H 0.1171 1.0733 0.1382 0.029 Uiso 1 1 calc R . . H13B H 0.1916 0.9749 0.1516 0.029 Uiso 1 1 calc R . . C14 C 0.20797(13) 1.01124(9) 0.08672(4) 0.0280(3) Uani 1 1 d . . . H14A H 0.2057 0.9472 0.0724 0.034 Uiso 1 1 calc R . . H14B H 0.1633 1.0579 0.0660 0.034 Uiso 1 1 calc R . . C15 C 0.35206(14) 1.04166(12) 0.09712(6) 0.0422(4) Uani 1 1 d . . . H15A H 0.3952 1.0513 0.0697 0.063 Uiso 1 1 calc R . . H15B H 0.3994 0.9913 0.1145 0.063 Uiso 1 1 calc R . . H15C H 0.3545 1.1020 0.1138 0.063 Uiso 1 1 calc R . . C16 C -0.06196(12) 0.94661(8) 0.16929(4) 0.0227(2) Uani 1 1 d . . . H16A H -0.1421 0.9050 0.1660 0.027 Uiso 1 1 calc R . . H16B H 0.0031 0.9151 0.1906 0.027 Uiso 1 1 calc R . . C17 C -0.10159(15) 1.04375(10) 0.18804(5) 0.0336(3) Uani 1 1 d . . . H17A H -0.0205 1.0833 0.1945 0.040 Uiso 1 1 calc R . . H17B H -0.1602 1.0784 0.1658 0.040 Uiso 1 1 calc R . . C18 C -0.17388(17) 1.03165(12) 0.22969(5) 0.0457(4) Uani 1 1 d . . . H18A H -0.1919 1.0952 0.2420 0.069 Uiso 1 1 calc R . . H18B H -0.1180 0.9943 0.2512 0.069 Uiso 1 1 calc R . . H18C H -0.2584 0.9977 0.2228 0.069 Uiso 1 1 calc R . . C19 C -0.09620(12) 0.99537(8) 0.08832(4) 0.0233(2) Uani 1 1 d . . . H19A H -0.1062 1.0652 0.0938 0.028 Uiso 1 1 calc R . . H19B H -0.0547 0.9882 0.0601 0.028 Uiso 1 1 calc R . . C20 C -0.23537(12) 0.95019(10) 0.08347(4) 0.0281(3) Uani 1 1 d . . . H20A H -0.2270 0.8792 0.0854 0.034 Uiso 1 1 calc R . . H20B H -0.2873 0.9721 0.1080 0.034 Uiso 1 1 calc R . . C21 C -0.31023(15) 0.97711(10) 0.03999(5) 0.0355(3) Uani 1 1 d . . . H21A H -0.3985 0.9466 0.0381 0.053 Uiso 1 1 calc R . . H21B H -0.2597 0.9548 0.0156 0.053 Uiso 1 1 calc R . . H21C H -0.3207 1.0473 0.0383 0.053 Uiso 1 1 calc R . . C1' C 0.71055(11) 0.79202(8) 0.34564(4) 0.0214(2) Uani 1 1 d . . . H1'A H 0.6647 0.8094 0.3185 0.026 Uiso 1 1 calc R . . C2' C 0.84534(12) 0.78199(9) 0.34809(4) 0.0265(3) Uani 1 1 d . . . H2'A H 0.8926 0.7928 0.3227 0.032 Uiso 1 1 calc R . . C3' C 0.91646(12) 0.75555(9) 0.38815(5) 0.0279(3) Uani 1 1 d . . . H3'A H 1.0106 0.7479 0.3892 0.034 Uiso 1 1 calc R . . C4' C 0.85078(11) 0.74112(8) 0.42495(4) 0.0237(2) Uani 1 1 d . . . H4'A H 0.8997 0.7239 0.4516 0.028 Uiso 1 1 calc R . . C4B C 0.70893(11) 0.75156(8) 0.42412(4) 0.0183(2) Uani 1 1 d . . . C5' C 0.43247(13) 0.74127(9) 0.50008(4) 0.0237(2) Uani 1 1 d . . . H5'A H 0.4798 0.7224 0.5268 0.028 Uiso 1 1 calc R . . C6' C 0.29958(13) 0.75912(9) 0.49944(4) 0.0271(3) Uani 1 1 d . . . H6'A H 0.2551 0.7544 0.5258 0.033 Uiso 1 1 calc R . . C7' C 0.22671(12) 0.78487(9) 0.45963(4) 0.0246(2) Uani 1 1 d . . . H7'A H 0.1338 0.7976 0.4596 0.030 Uiso 1 1 calc R . . C8' C 0.28822(11) 0.79162(8) 0.42136(4) 0.0200(2) Uani 1 1 d . . . H8'A H 0.2372 0.8075 0.3949 0.024 Uiso 1 1 calc R . . C9' C 0.49711(10) 0.78605(7) 0.38220(3) 0.0153(2) Uani 1 1 d . . . C8B C 0.42841(10) 0.77504(7) 0.42053(3) 0.0158(2) Uani 1 1 d . . . C9B C 0.63644(10) 0.77671(7) 0.38343(3) 0.0164(2) Uani 1 1 d . . . C10' C 0.64027(11) 0.73834(8) 0.46172(4) 0.0193(2) Uani 1 1 d . . . H10B H 0.6886 0.7206 0.4884 0.023 Uiso 1 1 calc R . . C10B C 0.50242(11) 0.75048(8) 0.46107(3) 0.0178(2) Uani 1 1 d . . . C11' C 0.41606(10) 0.80599(8) 0.33972(3) 0.0168(2) Uani 1 1 d . . . O1' O 0.33370(8) 0.75028(6) 0.32382(3) 0.02438(18) Uani 1 1 d . . . O2' O 0.44640(7) 0.89172(5) 0.32337(2) 0.01633(16) Uani 1 1 d . . . C12' C 0.37002(11) 0.93294(8) 0.28382(3) 0.0172(2) Uani 1 1 d . . . C13' C 0.44488(12) 1.02797(8) 0.27879(4) 0.0205(2) Uani 1 1 d . . . H13C H 0.4484 1.0626 0.3072 0.025 Uiso 1 1 calc R . . H13D H 0.5379 1.0129 0.2724 0.025 Uiso 1 1 calc R . . C14' C 0.38539(15) 1.09551(10) 0.24309(4) 0.0333(3) Uani 1 1 d . . . H14C H 0.3865 1.0633 0.2142 0.040 Uiso 1 1 calc R . . H14D H 0.2913 1.1094 0.2485 0.040 Uiso 1 1 calc R . . C15' C 0.46216(14) 1.18912(10) 0.24206(5) 0.0392(4) Uani 1 1 d . . . H15D H 0.4242 1.2293 0.2179 0.059 Uiso 1 1 calc R . . H15E H 0.5560 1.1754 0.2377 0.059 Uiso 1 1 calc R . . H15F H 0.4561 1.2233 0.2699 0.059 Uiso 1 1 calc R . . C16' C 0.37647(12) 0.86652(9) 0.24380(4) 0.0216(2) Uani 1 1 d . . . H16C H 0.3124 0.8131 0.2467 0.026 Uiso 1 1 calc R . . H16D H 0.3460 0.9035 0.2172 0.026 Uiso 1 1 calc R . . C17' C 0.51264(13) 0.82308(10) 0.23653(4) 0.0308(3) Uani 1 1 d . . . H17C H 0.5820 0.8734 0.2416 0.037 Uiso 1 1 calc R . . H17D H 0.5322 0.7711 0.2583 0.037 Uiso 1 1 calc R . . C18' C 0.51992(16) 0.78226(13) 0.19065(5) 0.0427(4) Uani 1 1 d . . . H18D H 0.6073 0.7521 0.1882 0.064 Uiso 1 1 calc R . . H18E H 0.5076 0.8344 0.1691 0.064 Uiso 1 1 calc R . . H18F H 0.4496 0.7339 0.1851 0.064 Uiso 1 1 calc R . . C19' C 0.22520(11) 0.94851(8) 0.29477(4) 0.0194(2) Uani 1 1 d . . . H19C H 0.1747 0.9757 0.2686 0.023 Uiso 1 1 calc R . . H19D H 0.1856 0.8850 0.3008 0.023 Uiso 1 1 calc R . . C20' C 0.20650(11) 1.01478(9) 0.33380(4) 0.0219(2) Uani 1 1 d . . . H20C H 0.2695 0.9954 0.3587 0.026 Uiso 1 1 calc R . . H20D H 0.2282 1.0817 0.3257 0.026 Uiso 1 1 calc R . . C21' C 0.06504(12) 1.01164(10) 0.34835(5) 0.0303(3) Uani 1 1 d . . . H21D H 0.0573 1.0563 0.3729 0.045 Uiso 1 1 calc R . . H21E H 0.0445 0.9461 0.3577 0.045 Uiso 1 1 calc R . . H21F H 0.0021 1.0305 0.3238 0.045 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 C1 0.0186(5) 0.0206(5) 0.0225(5) 0.0014(4) 0.0000(4) -0.0008(4) C2 0.0178(5) 0.0288(6) 0.0301(6) 0.0052(5) 0.0045(5) -0.0015(5) C3 0.0206(6) 0.0325(7) 0.0267(6) 0.0038(5) 0.0081(5) 0.0053(5) C4 0.0243(6) 0.0236(6) 0.0225(5) -0.0002(4) 0.0058(4) 0.0070(5) C4A 0.0190(5) 0.0160(5) 0.0174(5) 0.0025(4) 0.0022(4) 0.0038(4) C5 0.0240(6) 0.0130(5) 0.0226(5) 0.0000(4) -0.0006(4) -0.0017(4) C6 0.0209(5) 0.0189(5) 0.0286(6) 0.0014(4) 0.0001(4) -0.0050(4) C7 0.0190(5) 0.0217(6) 0.0277(6) 0.0003(5) 0.0053(4) -0.0002(4) C8 0.0196(5) 0.0164(5) 0.0213(5) -0.0021(4) 0.0029(4) 0.0012(4) C8A 0.0167(5) 0.0137(5) 0.0163(5) 0.0011(4) 0.0003(4) 0.0010(4) C9 0.0167(5) 0.0136(5) 0.0158(5) 0.0006(4) -0.0005(4) 0.0016(4) C9A 0.0163(5) 0.0159(5) 0.0167(5) 0.0022(4) 0.0002(4) 0.0020(4) C10 0.0231(5) 0.0139(5) 0.0179(5) -0.0009(4) 0.0007(4) 0.0037(4) C10A 0.0189(5) 0.0127(5) 0.0171(5) 0.0013(4) -0.0005(4) 0.0017(4) C11 0.0151(5) 0.0155(5) 0.0203(5) 0.0004(4) 0.0013(4) -0.0007(4) O1 0.0271(4) 0.0246(4) 0.0238(4) -0.0056(3) -0.0066(3) 0.0035(3) O2 0.0216(4) 0.0122(4) 0.0201(4) -0.0020(3) -0.0006(3) 0.0017(3) C12 0.0228(5) 0.0118(5) 0.0238(5) -0.0028(4) 0.0029(4) 0.0012(4) C13 0.0260(6) 0.0155(5) 0.0303(6) -0.0028(5) 0.0032(5) -0.0033(4) C14 0.0269(6) 0.0215(6) 0.0363(7) 0.0024(5) 0.0078(5) -0.0017(5) C15 0.0284(7) 0.0387(8) 0.0605(10) 0.0080(7) 0.0089(7) -0.0071(6) C16 0.0257(6) 0.0194(5) 0.0236(5) -0.0036(4) 0.0051(4) -0.0001(4) C17 0.0386(7) 0.0242(6) 0.0397(7) -0.0106(5) 0.0141(6) 0.0002(5) C18 0.0505(9) 0.0471(9) 0.0420(8) -0.0153(7) 0.0193(7) 0.0036(7) C19 0.0277(6) 0.0160(5) 0.0259(6) 0.0007(4) 0.0009(5) 0.0042(4) C20 0.0259(6) 0.0253(6) 0.0325(6) -0.0003(5) -0.0006(5) 0.0046(5) C21 0.0346(7) 0.0288(7) 0.0414(8) -0.0021(6) -0.0089(6) 0.0080(6) C1' 0.0203(5) 0.0228(6) 0.0215(5) -0.0052(4) 0.0027(4) -0.0011(4) C2' 0.0209(6) 0.0276(6) 0.0321(6) -0.0081(5) 0.0081(5) -0.0012(5) C3' 0.0158(5) 0.0247(6) 0.0433(7) -0.0062(5) 0.0013(5) 0.0016(4) C4' 0.0175(5) 0.0174(5) 0.0350(6) -0.0012(5) -0.0057(5) 0.0019(4) C4B 0.0176(5) 0.0119(5) 0.0250(5) -0.0023(4) -0.0028(4) 0.0005(4) C5' 0.0317(6) 0.0226(6) 0.0166(5) 0.0004(4) 0.0009(4) -0.0062(5) C6' 0.0314(6) 0.0295(6) 0.0213(6) -0.0028(5) 0.0086(5) -0.0093(5) C7' 0.0204(5) 0.0264(6) 0.0276(6) -0.0038(5) 0.0054(5) -0.0052(5) C8' 0.0179(5) 0.0206(5) 0.0213(5) -0.0007(4) 0.0006(4) -0.0027(4) C9' 0.0161(5) 0.0127(5) 0.0168(5) -0.0003(4) -0.0004(4) -0.0009(4) C8B 0.0173(5) 0.0126(5) 0.0173(5) -0.0001(4) 0.0000(4) -0.0019(4) C9B 0.0163(5) 0.0124(5) 0.0204(5) -0.0026(4) 0.0004(4) -0.0003(4) C10' 0.0222(5) 0.0150(5) 0.0198(5) 0.0009(4) -0.0052(4) -0.0008(4) C10B 0.0226(5) 0.0132(5) 0.0173(5) -0.0005(4) -0.0007(4) -0.0031(4) C11' 0.0171(5) 0.0169(5) 0.0163(5) -0.0005(4) 0.0014(4) -0.0003(4) O1' 0.0268(4) 0.0207(4) 0.0244(4) 0.0014(3) -0.0065(3) -0.0064(3) O2' 0.0179(4) 0.0158(4) 0.0149(3) 0.0015(3) -0.0014(3) -0.0012(3) C12' 0.0201(5) 0.0170(5) 0.0142(5) 0.0014(4) -0.0017(4) 0.0015(4) C13' 0.0235(5) 0.0182(5) 0.0202(5) 0.0022(4) 0.0034(4) 0.0005(4) C14' 0.0423(8) 0.0275(7) 0.0296(6) 0.0109(5) -0.0009(6) 0.0010(6) C15' 0.0360(7) 0.0285(7) 0.0549(9) 0.0209(6) 0.0154(7) 0.0061(6) C16' 0.0259(6) 0.0227(6) 0.0159(5) -0.0029(4) -0.0015(4) 0.0023(4) C17' 0.0288(6) 0.0376(7) 0.0259(6) -0.0115(5) 0.0017(5) 0.0043(5) C18' 0.0453(8) 0.0533(10) 0.0298(7) -0.0175(7) 0.0039(6) 0.0122(7) C19' 0.0193(5) 0.0199(5) 0.0185(5) -0.0005(4) -0.0014(4) 0.0004(4) C20' 0.0199(5) 0.0219(6) 0.0237(5) -0.0039(4) 0.0016(4) 0.0003(4) C21' 0.0216(6) 0.0344(7) 0.0354(7) -0.0094(6) 0.0059(5) -0.0011(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 C2 1.3646(16) . ? C1 C9A 1.4315(15) . ? C1 H1A 0.9500 . ? C2 C3 1.4190(18) . ? C2 H2A 0.9500 . ? C3 C4 1.3605(17) . ? C3 H3A 0.9500 . ? C4 C4A 1.4314(15) . ? C4 H4A 0.9500 . ? C4A C10 1.3936(15) . ? C4A C9A 1.4352(15) . ? C5 C6 1.3610(16) . ? C5 C10A 1.4278(15) . ? C5 H5A 0.9500 . ? C6 C7 1.4224(16) . ? C6 H6A 0.9500 . ? C7 C8 1.3622(16) . ? C7 H7A 0.9500 . ? C8 C8A 1.4312(14) . ? C8 H8A 0.9500 . ? C8A C9 1.4065(14) . ? C8A C10A 1.4321(14) . ? C9 C9A 1.4048(14) . ? C9 C11 1.5010(15) . ? C10 C10A 1.3970(15) . ? C10 H10A 0.9500 . ? C11 O1 1.2044(13) . ? C11 O2 1.3390(13) . ? O2 C12 1.4946(13) . ? C12 C13 1.5276(16) . ? C12 C19 1.5311(16) . ? C12 C16 1.5342(15) . ? C13 C14 1.5274(17) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5188(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.5283(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5187(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.5293(17) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.5242(19) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C1' C2' 1.3576(16) . ? C1' C9B 1.4337(15) . ? C1' H1'A 0.9500 . ? C2' C3' 1.4192(19) . ? C2' H2'A 0.9500 . ? C3' C4' 1.3585(18) . ? C3' H3'A 0.9500 . ? C4' C4B 1.4305(15) . ? C4' H4'A 0.9500 . ? C4B C10' 1.3936(16) . ? C4B C9B 1.4367(15) . ? C5' C6' 1.3562(18) . ? C5' C10B 1.4320(15) . ? C5' H5'A 0.9500 . ? C6' C7' 1.4183(18) . ? C6' H6'A 0.9500 . ? C7' C8' 1.3641(16) . ? C7' H7'A 0.9500 . ? C8' C8B 1.4288(15) . ? C8' H8'A 0.9500 . ? C9' C9B 1.4032(14) . ? C9' C8B 1.4096(14) . ? C9' C11' 1.5061(15) . ? C8B C10B 1.4376(15) . ? C10' C10B 1.3935(16) . ? C10' H10B 0.9500 . ? C11' O1' 1.2078(13) . ? C11' O2' 1.3337(13) . ? O2' C12' 1.4965(12) . ? C12' C13' 1.5310(15) . ? C12' C19' 1.5313(15) . ? C12' C16' 1.5355(15) . ? C13' C14' 1.5259(17) . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' C15' 1.512(2) . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C16' C17' 1.5257(17) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' C18' 1.5175(18) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C18' H18D 0.9800 . ? C18' H18E 0.9800 . ? C18' H18F 0.9800 . ? C19' C20' 1.5276(15) . ? C19' H19C 0.9900 . ? C19' H19D 0.9900 . ? C20' C21' 1.5198(16) . ? C20' H20C 0.9900 . ? C20' H20D 0.9900 . ? C21' H21D 0.9800 . ? C21' H21E 0.9800 . ? C21' H21F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.86(11) . . ? C2 C1 H1A 119.6 . . ? C9A C1 H1A 119.6 . . ? C1 C2 C3 120.74(11) . . ? C1 C2 H2A 119.6 . . ? C3 C2 H2A 119.6 . . ? C4 C3 C2 120.24(10) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C4A 121.14(11) . . ? C3 C4 H4A 119.4 . . ? C4A C4 H4A 119.4 . . ? C10 C4A C4 121.81(10) . . ? C10 C4A C9A 119.56(9) . . ? C4 C4A C9A 118.62(10) . . ? C6 C5 C10A 121.05(10) . . ? C6 C5 H5A 119.5 . . ? C10A C5 H5A 119.5 . . ? C5 C6 C7 120.10(10) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C8 C7 C6 120.77(10) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C8A 120.81(10) . . ? C7 C8 H8A 119.6 . . ? C8A C8 H8A 119.6 . . ? C9 C8A C8 122.73(10) . . ? C9 C8A C10A 118.90(9) . . ? C8 C8A C10A 118.37(9) . . ? C9A C9 C8A 121.57(10) . . ? C9A C9 C11 118.96(9) . . ? C8A C9 C11 119.45(9) . . ? C9 C9A C1 122.76(10) . . ? C9 C9A C4A 118.83(10) . . ? C1 C9A C4A 118.39(9) . . ? C4A C10 C10A 121.61(10) . . ? C4A C10 H10A 119.2 . . ? C10A C10 H10A 119.2 . . ? C10 C10A C5 121.59(10) . . ? C10 C10A C8A 119.52(10) . . ? C5 C10A C8A 118.89(9) . . ? O1 C11 O2 126.56(10) . . ? O1 C11 C9 124.22(10) . . ? O2 C11 C9 109.21(9) . . ? C11 O2 C12 122.94(8) . . ? O2 C12 C13 109.63(9) . . ? O2 C12 C19 101.11(8) . . ? C13 C12 C19 111.79(10) . . ? O2 C12 C16 108.38(9) . . ? C13 C12 C16 111.89(10) . . ? C19 C12 C16 113.40(9) . . ? C14 C13 C12 116.36(10) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? C15 C14 C13 110.96(12) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C12 114.12(10) . . ? C17 C16 H16A 108.7 . . ? C12 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C12 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 111.69(12) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C12 115.79(10) . . ? C20 C19 H19A 108.3 . . ? C12 C19 H19A 108.3 . . ? C20 C19 H19B 108.3 . . ? C12 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? C21 C20 C19 111.93(11) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2' C1' C9B 120.96(11) . . ? C2' C1' H1'A 119.5 . . ? C9B C1' H1'A 119.5 . . ? C1' C2' C3' 120.76(11) . . ? C1' C2' H2'A 119.6 . . ? C3' C2' H2'A 119.6 . . ? C4' C3' C2' 120.45(11) . . ? C4' C3' H3'A 119.8 . . ? C2' C3' H3'A 119.8 . . ? C3' C4' C4B 120.88(11) . . ? C3' C4' H4'A 119.6 . . ? C4B C4' H4'A 119.6 . . ? C10' C4B C4' 121.59(10) . . ? C10' C4B C9B 119.62(10) . . ? C4' C4B C9B 118.79(10) . . ? C6' C5' C10B 120.89(11) . . ? C6' C5' H5'A 119.6 . . ? C10B C5' H5'A 119.6 . . ? C5' C6' C7' 120.30(11) . . ? C5' C6' H6'A 119.8 . . ? C7' C6' H6'A 119.8 . . ? C8' C7' C6' 120.91(11) . . ? C8' C7' H7'A 119.5 . . ? C6' C7' H7'A 119.5 . . ? C7' C8' C8B 120.81(11) . . ? C7' C8' H8'A 119.6 . . ? C8B C8' H8'A 119.6 . . ? C9B C9' C8B 121.00(10) . . ? C9B C9' C11' 121.05(9) . . ? C8B C9' C11' 117.93(9) . . ? C9' C8B C8' 122.66(10) . . ? C9' C8B C10B 119.13(9) . . ? C8' C8B C10B 118.14(9) . . ? C9' C9B C1' 122.67(10) . . ? C9' C9B C4B 119.18(9) . . ? C1' C9B C4B 118.15(10) . . ? C10B C10' C4B 121.53(10) . . ? C10B C10' H10B 119.2 . . ? C4B C10' H10B 119.2 . . ? C10' C10B C5' 121.62(10) . . ? C10' C10B C8B 119.48(10) . . ? C5' C10B C8B 118.88(10) . . ? O1' C11' O2' 126.08(10) . . ? O1' C11' C9' 122.69(10) . . ? O2' C11' C9' 111.23(9) . . ? C11' O2' C12' 121.67(8) . . ? O2' C12' C13' 100.57(8) . . ? O2' C12' C19' 108.50(8) . . ? C13' C12' C19' 112.44(9) . . ? O2' C12' C16' 111.35(9) . . ? C13' C12' C16' 112.80(9) . . ? C19' C12' C16' 110.72(9) . . ? C14' C13' C12' 115.52(10) . . ? C14' C13' H13C 108.4 . . ? C12' C13' H13C 108.4 . . ? C14' C13' H13D 108.4 . . ? C12' C13' H13D 108.4 . . ? H13C C13' H13D 107.5 . . ? C15' C14' C13' 111.62(12) . . ? C15' C14' H14C 109.3 . . ? C13' C14' H14C 109.3 . . ? C15' C14' H14D 109.3 . . ? C13' C14' H14D 109.3 . . ? H14C C14' H14D 108.0 . . ? C14' C15' H15D 109.5 . . ? C14' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C14' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C17' C16' C12' 116.29(10) . . ? C17' C16' H16C 108.2 . . ? C12' C16' H16C 108.2 . . ? C17' C16' H16D 108.2 . . ? C12' C16' H16D 108.2 . . ? H16C C16' H16D 107.4 . . ? C18' C17' C16' 112.68(11) . . ? C18' C17' H17C 109.1 . . ? C16' C17' H17C 109.1 . . ? C18' C17' H17D 109.1 . . ? C16' C17' H17D 109.1 . . ? H17C C17' H17D 107.8 . . ? C17' C18' H18D 109.5 . . ? C17' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C17' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C20' C19' C12' 115.32(9) . . ? C20' C19' H19C 108.4 . . ? C12' C19' H19C 108.4 . . ? C20' C19' H19D 108.4 . . ? C12' C19' H19D 108.4 . . ? H19C C19' H19D 107.5 . . ? C21' C20' C19' 112.41(10) . . ? C21' C20' H20C 109.1 . . ? C19' C20' H20C 109.1 . . ? C21' C20' H20D 109.1 . . ? C19' C20' H20D 109.1 . . ? H20C C20' H20D 107.9 . . ? C20' C21' H21D 109.5 . . ? C20' C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? C20' C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 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 C9A C1 C2 C3 -0.26(18) . . . . ? C1 C2 C3 C4 0.61(19) . . . . ? C2 C3 C4 C4A -0.19(18) . . . . ? C3 C4 C4A C10 178.86(11) . . . . ? C3 C4 C4A C9A -0.56(17) . . . . ? C10A C5 C6 C7 -0.19(18) . . . . ? C5 C6 C7 C8 0.24(18) . . . . ? C6 C7 C8 C8A 0.37(18) . . . . ? C7 C8 C8A C9 178.83(11) . . . . ? C7 C8 C8A C10A -1.00(16) . . . . ? C8 C8A C9 C9A 179.97(10) . . . . ? C10A C8A C9 C9A -0.20(15) . . . . ? C8 C8A C9 C11 -1.88(16) . . . . ? C10A C8A C9 C11 177.95(9) . . . . ? C8A C9 C9A C1 178.63(10) . . . . ? C11 C9 C9A C1 0.46(16) . . . . ? C8A C9 C9A C4A -0.05(15) . . . . ? C11 C9 C9A C4A -178.21(9) . . . . ? C2 C1 C9A C9 -179.17(11) . . . . ? C2 C1 C9A C4A -0.49(16) . . . . ? C10 C4A C9A C9 0.19(15) . . . . ? C4 C4A C9A C9 179.62(10) . . . . ? C10 C4A C9A C1 -178.54(10) . . . . ? C4 C4A C9A C1 0.89(15) . . . . ? C4 C4A C10 C10A -179.49(10) . . . . ? C9A C4A C10 C10A -0.07(16) . . . . ? C4A C10 C10A C5 178.92(10) . . . . ? C4A C10 C10A C8A -0.18(16) . . . . ? C6 C5 C10A C10 -179.56(11) . . . . ? C6 C5 C10A C8A -0.45(16) . . . . ? C9 C8A C10A C10 0.32(15) . . . . ? C8 C8A C10A C10 -179.85(10) . . . . ? C9 C8A C10A C5 -178.81(10) . . . . ? C8 C8A C10A C5 1.03(15) . . . . ? C9A C9 C11 O1 -70.47(14) . . . . ? C8A C9 C11 O1 111.33(12) . . . . ? C9A C9 C11 O2 108.68(11) . . . . ? C8A C9 C11 O2 -69.53(12) . . . . ? O1 C11 O2 C12 1.67(16) . . . . ? C9 C11 O2 C12 -177.45(8) . . . . ? C11 O2 C12 C13 58.23(13) . . . . ? C11 O2 C12 C19 176.38(9) . . . . ? C11 O2 C12 C16 -64.16(12) . . . . ? O2 C12 C13 C14 55.42(13) . . . . ? C19 C12 C13 C14 -55.86(13) . . . . ? C16 C12 C13 C14 175.70(10) . . . . ? C12 C13 C14 C15 -165.24(11) . . . . ? O2 C12 C16 C17 -173.61(10) . . . . ? C13 C12 C16 C17 65.38(14) . . . . ? C19 C12 C16 C17 -62.20(14) . . . . ? C12 C16 C17 C18 174.38(12) . . . . ? O2 C12 C19 C20 66.20(11) . . . . ? C13 C12 C19 C20 -177.22(10) . . . . ? C16 C12 C19 C20 -49.59(13) . . . . ? C12 C19 C20 C21 -165.30(10) . . . . ? C9B C1' C2' C3' 0.33(18) . . . . ? C1' C2' C3' C4' -0.92(19) . . . . ? C2' C3' C4' C4B 0.42(18) . . . . ? C3' C4' C4B C10' -179.09(11) . . . . ? C3' C4' C4B C9B 0.63(16) . . . . ? C10B C5' C6' C7' 1.68(18) . . . . ? C5' C6' C7' C8' 0.38(19) . . . . ? C6' C7' C8' C8B -1.42(18) . . . . ? C9B C9' C8B C8' 174.81(10) . . . . ? C11' C9' C8B C8' -6.50(15) . . . . ? C9B C9' C8B C10B -2.24(15) . . . . ? C11' C9' C8B C10B 176.45(9) . . . . ? C7' C8' C8B C9' -176.68(11) . . . . ? C7' C8' C8B C10B 0.40(16) . . . . ? C8B C9' C9B C1' -176.87(10) . . . . ? C11' C9' C9B C1' 4.48(16) . . . . ? C8B C9' C9B C4B 2.63(15) . . . . ? C11' C9' C9B C4B -176.02(9) . . . . ? C2' C1' C9B C9' -179.78(11) . . . . ? C2' C1' C9B C4B 0.72(16) . . . . ? C10' C4B C9B C9' -0.98(15) . . . . ? C4' C4B C9B C9' 179.30(10) . . . . ? C10' C4B C9B C1' 178.54(10) . . . . ? C4' C4B C9B C1' -1.18(15) . . . . ? C4' C4B C10' C10B 178.65(10) . . . . ? C9B C4B C10' C10B -1.06(16) . . . . ? C4B C10' C10B C5' -177.09(10) . . . . ? C4B C10' C10B C8B 1.45(16) . . . . ? C6' C5' C10B C10' 175.90(11) . . . . ? C6' C5' C10B C8B -2.65(17) . . . . ? C9' C8B C10B C10' 0.19(15) . . . . ? C8' C8B C10B C10' -176.99(10) . . . . ? C9' C8B C10B C5' 178.77(10) . . . . ? C8' C8B C10B C5' 1.59(15) . . . . ? C9B C9' C11' O1' 116.86(12) . . . . ? C8B C9' C11' O1' -61.84(14) . . . . ? C9B C9' C11' O2' -64.09(13) . . . . ? C8B C9' C11' O2' 117.22(10) . . . . ? O1' C11' O2' C12' 5.38(16) . . . . ? C9' C11' O2' C12' -173.64(8) . . . . ? C11' O2' C12' C13' -179.05(9) . . . . ? C11' O2' C12' C19' 62.80(12) . . . . ? C11' O2' C12' C16' -59.30(12) . . . . ? O2' C12' C13' C14' -174.67(9) . . . . ? C19' C12' C13' C14' -59.44(13) . . . . ? C16' C12' C13' C14' 66.64(13) . . . . ? C12' C13' C14' C15' 177.31(11) . . . . ? O2' C12' C16' C17' -43.34(14) . . . . ? C13' C12' C16' C17' 68.86(13) . . . . ? C19' C12' C16' C17' -164.15(10) . . . . ? C12' C16' C17' C18' -164.03(12) . . . . ? O2' C12' C19' C20' 58.31(12) . . . . ? C13' C12' C19' C20' -52.02(13) . . . . ? C16' C12' C19' C20' -179.22(10) . . . . ? C12' C19' C20' C21' -168.81(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.352 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.047 # Attachment 'cb16_0m_TEAE.cif' data_cb16_0m _database_code_depnum_ccdc_archive 'CCDC 808564' #TrackingRef 'cb16_0m_TEAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 O2' _chemical_formula_weight 320.41 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 P2(1)/c 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 7.6558(4) _cell_length_b 17.7701(9) _cell_length_c 12.6438(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.1985(7) _cell_angle_gamma 90.00 _cell_volume 1706.56(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9948 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 31.33 _exptl_crystal_description 'prism frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9676 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 31489 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4793 _reflns_number_gt 4330 _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^)+(0.0639P)^2^+0.4378P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4793 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1058 _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 -0.13665(11) 0.58186(5) 0.79464(7) 0.01717(16) Uani 1 1 d . . . H1 H -0.0849 0.5818 0.7302 0.021 Uiso 1 1 calc R . . C2 C -0.19410(11) 0.64791(5) 0.83284(7) 0.02035(17) Uani 1 1 d . . . H2 H -0.1815 0.6933 0.7947 0.024 Uiso 1 1 calc R . . C3 C -0.27260(12) 0.64992(5) 0.92885(7) 0.02049(17) Uani 1 1 d . . . H3 H -0.3117 0.6964 0.9546 0.025 Uiso 1 1 calc R . . C4 C -0.29188(11) 0.58524(5) 0.98401(7) 0.01770(16) Uani 1 1 d . . . H4 H -0.3447 0.5870 1.0481 0.021 Uiso 1 1 calc R . . C5 C -0.22016(11) 0.31056(5) 1.02289(7) 0.01923(17) Uani 1 1 d . . . H5 H -0.2748 0.3119 1.0863 0.023 Uiso 1 1 calc R . . C6 C -0.16602(11) 0.24343(5) 0.98663(8) 0.02156(18) Uani 1 1 d . . . H6 H -0.1828 0.1985 1.0247 0.026 Uiso 1 1 calc R . . C7 C -0.08418(11) 0.24066(5) 0.89159(8) 0.02084(18) Uani 1 1 d . . . H7 H -0.0473 0.1936 0.8665 0.025 Uiso 1 1 calc R . . C8 C -0.05796(11) 0.30466(5) 0.83611(7) 0.01765(16) Uani 1 1 d . . . H8 H -0.0032 0.3015 0.7729 0.021 Uiso 1 1 calc R . . C9 C -0.09191(10) 0.44345(4) 0.81576(6) 0.01340(15) Uani 1 1 d . . . C9A C -0.15326(10) 0.51271(4) 0.85039(6) 0.01322(15) Uani 1 1 d . . . C10 C -0.25348(10) 0.44806(5) 1.00249(6) 0.01566(16) Uani 1 1 d . . . H10 H -0.3073 0.4497 1.0662 0.019 Uiso 1 1 calc R . . C11 C -0.00570(10) 0.44286(5) 0.71539(6) 0.01569(16) Uani 1 1 d . . . O1 O -0.08227(9) 0.45831(5) 0.62877(5) 0.02836(17) Uani 1 1 d . . . O2 O 0.16467(7) 0.42502(3) 0.73715(4) 0.01418(13) Uani 1 1 d . . . C12 C 0.28691(10) 0.42601(5) 0.65439(6) 0.01469(15) Uani 1 1 d . . . C13 C 0.30301(12) 0.50667(5) 0.61382(7) 0.01894(17) Uani 1 1 d . . . H13A H 0.3946 0.5075 0.5651 0.023 Uiso 1 1 calc R . . H13B H 0.1900 0.5207 0.5715 0.023 Uiso 1 1 calc R . . C14 C 0.34867(12) 0.56654(5) 0.69958(7) 0.01978(17) Uani 1 1 d . . . H14A H 0.2558 0.5685 0.7463 0.030 Uiso 1 1 calc R . . H14B H 0.3584 0.6157 0.6657 0.030 Uiso 1 1 calc R . . H14C H 0.4610 0.5538 0.7418 0.030 Uiso 1 1 calc R . . C15 C 0.21785(10) 0.37227(5) 0.56346(6) 0.01674(16) Uani 1 1 d . . . H15A H 0.1874 0.3236 0.5946 0.020 Uiso 1 1 calc R . . H15B H 0.1085 0.3936 0.5249 0.020 Uiso 1 1 calc R . . C16 C 0.34829(12) 0.35778(6) 0.48365(7) 0.02300(19) Uani 1 1 d . . . H16A H 0.3711 0.4049 0.4475 0.034 Uiso 1 1 calc R . . H16B H 0.2987 0.3207 0.4309 0.034 Uiso 1 1 calc R . . H16C H 0.4588 0.3384 0.5214 0.034 Uiso 1 1 calc R . . C17 C 0.45883(10) 0.39857(5) 0.71811(7) 0.01731(16) Uani 1 1 d . . . H17A H 0.5546 0.4030 0.6726 0.021 Uiso 1 1 calc R . . H17B H 0.4882 0.4323 0.7801 0.021 Uiso 1 1 calc R . . C18 C 0.45396(11) 0.31776(5) 0.75822(8) 0.02174(18) Uani 1 1 d . . . H18A H 0.3509 0.3109 0.7960 0.033 Uiso 1 1 calc R . . H18B H 0.5612 0.3073 0.8069 0.033 Uiso 1 1 calc R . . H18C H 0.4466 0.2831 0.6976 0.033 Uiso 1 1 calc R . . C4A C -0.23372(10) 0.51470(5) 0.94681(6) 0.01417(15) Uani 1 1 d . . . C10A C -0.19615(10) 0.37905(5) 0.96704(6) 0.01503(15) Uani 1 1 d . . . C8A C -0.11180(10) 0.37648(4) 0.87184(6) 0.01398(15) 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 0.0154(3) 0.0184(4) 0.0178(4) 0.0038(3) 0.0026(3) -0.0008(3) C2 0.0194(4) 0.0166(4) 0.0247(4) 0.0034(3) 0.0012(3) 0.0001(3) C3 0.0200(4) 0.0172(4) 0.0236(4) -0.0030(3) 0.0001(3) 0.0023(3) C4 0.0169(4) 0.0196(4) 0.0164(4) -0.0031(3) 0.0015(3) 0.0014(3) C5 0.0171(4) 0.0211(4) 0.0196(4) 0.0052(3) 0.0025(3) -0.0023(3) C6 0.0183(4) 0.0180(4) 0.0278(4) 0.0064(3) 0.0008(3) -0.0018(3) C7 0.0162(4) 0.0160(4) 0.0299(4) -0.0001(3) 0.0014(3) 0.0010(3) C8 0.0140(3) 0.0175(4) 0.0214(4) -0.0013(3) 0.0021(3) 0.0007(3) C9 0.0106(3) 0.0171(4) 0.0124(3) 0.0003(3) 0.0013(2) 0.0001(3) C9A 0.0101(3) 0.0159(4) 0.0134(3) 0.0007(3) 0.0006(2) -0.0007(3) C10 0.0144(3) 0.0195(4) 0.0133(3) 0.0008(3) 0.0026(3) -0.0010(3) C11 0.0137(3) 0.0188(4) 0.0147(3) 0.0004(3) 0.0026(3) 0.0013(3) O1 0.0219(3) 0.0489(4) 0.0142(3) 0.0039(3) 0.0018(2) 0.0130(3) O2 0.0113(3) 0.0195(3) 0.0122(3) 0.0009(2) 0.00320(19) -0.0006(2) C12 0.0123(3) 0.0193(4) 0.0132(3) -0.0012(3) 0.0047(3) -0.0024(3) C13 0.0232(4) 0.0197(4) 0.0148(4) 0.0002(3) 0.0058(3) -0.0052(3) C14 0.0216(4) 0.0183(4) 0.0198(4) -0.0011(3) 0.0037(3) -0.0017(3) C15 0.0148(3) 0.0208(4) 0.0149(4) -0.0030(3) 0.0031(3) -0.0032(3) C16 0.0217(4) 0.0292(5) 0.0194(4) -0.0072(3) 0.0077(3) -0.0044(3) C17 0.0119(3) 0.0218(4) 0.0182(4) -0.0028(3) 0.0019(3) -0.0024(3) C18 0.0162(4) 0.0208(4) 0.0269(4) -0.0021(3) -0.0021(3) 0.0008(3) C4A 0.0118(3) 0.0170(4) 0.0134(3) -0.0006(3) 0.0006(3) -0.0003(3) C10A 0.0123(3) 0.0176(4) 0.0149(3) 0.0019(3) 0.0009(3) -0.0013(3) C8A 0.0107(3) 0.0158(4) 0.0152(3) 0.0002(3) 0.0005(3) -0.0004(3) _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 C2 1.3630(12) . ? C1 C9A 1.4302(11) . ? C1 H1 0.9500 . ? C2 C3 1.4209(13) . ? C2 H2 0.9500 . ? C3 C4 1.3620(12) . ? C3 H3 0.9500 . ? C4 C4A 1.4295(11) . ? C4 H4 0.9500 . ? C5 C6 1.3611(13) . ? C5 C10A 1.4306(11) . ? C5 H5 0.9500 . ? C6 C7 1.4241(13) . ? C6 H6 0.9500 . ? C7 C8 1.3642(12) . ? C7 H7 0.9500 . ? C8 C8A 1.4314(11) . ? C8 H8 0.9500 . ? C9 C8A 1.4034(11) . ? C9 C9A 1.4066(11) . ? C9 C11 1.5020(11) . ? C9A C4A 1.4335(11) . ? C10 C10A 1.3952(11) . ? C10 C4A 1.3955(11) . ? C10 H10 0.9500 . ? C11 O1 1.2074(10) . ? C11 O2 1.3370(9) . ? O2 C12 1.4888(9) . ? C12 C13 1.5325(12) . ? C12 C17 1.5340(11) . ? C12 C15 1.5366(11) . ? C13 C14 1.5279(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.5278(11) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.5250(12) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C10A C8A 1.4362(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.84(8) . . ? C2 C1 H1 119.6 . . ? C9A C1 H1 119.6 . . ? C1 C2 C3 120.94(8) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 120.06(8) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 120.89(8) . . ? C3 C4 H4 119.6 . . ? C4A C4 H4 119.6 . . ? C6 C5 C10A 121.06(8) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 119.95(8) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.91(8) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C8A 120.95(8) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C8A C9 C9A 121.55(7) . . ? C8A C9 C11 120.52(7) . . ? C9A C9 C11 117.93(7) . . ? C9 C9A C1 122.99(7) . . ? C9 C9A C4A 118.82(7) . . ? C1 C9A C4A 118.18(7) . . ? C10A C10 C4A 121.69(7) . . ? C10A C10 H10 119.2 . . ? C4A C10 H10 119.2 . . ? O1 C11 O2 126.21(8) . . ? O1 C11 C9 123.37(7) . . ? O2 C11 C9 110.39(7) . . ? C11 O2 C12 122.38(6) . . ? O2 C12 C13 109.29(6) . . ? O2 C12 C17 101.57(6) . . ? C13 C12 C17 111.93(7) . . ? O2 C12 C15 109.32(6) . . ? C13 C12 C15 111.43(7) . . ? C17 C12 C15 112.80(7) . . ? C14 C13 C12 115.75(7) . . ? C14 C13 H13A 108.3 . . ? C12 C13 H13A 108.3 . . ? C14 C13 H13B 108.3 . . ? C12 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C12 114.01(7) . . ? C16 C15 H15A 108.8 . . ? C12 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C12 C15 H15B 108.8 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C12 114.76(7) . . ? C18 C17 H17A 108.6 . . ? C12 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C12 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C4A C4 121.35(7) . . ? C10 C4A C9A 119.56(7) . . ? C4 C4A C9A 119.09(7) . . ? C10 C10A C5 121.61(7) . . ? C10 C10A C8A 119.33(7) . . ? C5 C10A C8A 119.06(7) . . ? C9 C8A C8 122.88(7) . . ? C9 C8A C10A 119.01(7) . . ? C8 C8A C10A 118.06(7) . . ? 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 C9A C1 C2 C3 -0.22(13) . . . . ? C1 C2 C3 C4 -0.19(13) . . . . ? C2 C3 C4 C4A 0.11(13) . . . . ? C10A C5 C6 C7 -0.07(13) . . . . ? C5 C6 C7 C8 0.38(13) . . . . ? C6 C7 C8 C8A 0.05(13) . . . . ? C8A C9 C9A C1 -179.39(7) . . . . ? C11 C9 C9A C1 -0.16(11) . . . . ? C8A C9 C9A C4A 1.64(11) . . . . ? C11 C9 C9A C4A -179.13(7) . . . . ? C2 C1 C9A C9 -178.29(8) . . . . ? C2 C1 C9A C4A 0.69(12) . . . . ? C8A C9 C11 O1 114.71(10) . . . . ? C9A C9 C11 O1 -64.53(12) . . . . ? C8A C9 C11 O2 -66.86(9) . . . . ? C9A C9 C11 O2 113.90(8) . . . . ? O1 C11 O2 C12 3.35(13) . . . . ? C9 C11 O2 C12 -175.02(6) . . . . ? C11 O2 C12 C13 63.93(9) . . . . ? C11 O2 C12 C17 -177.68(7) . . . . ? C11 O2 C12 C15 -58.27(9) . . . . ? O2 C12 C13 C14 51.78(9) . . . . ? C17 C12 C13 C14 -59.94(9) . . . . ? C15 C12 C13 C14 172.70(7) . . . . ? O2 C12 C15 C16 -169.65(7) . . . . ? C13 C12 C15 C16 69.44(9) . . . . ? C17 C12 C15 C16 -57.44(10) . . . . ? O2 C12 C17 C18 65.23(8) . . . . ? C13 C12 C17 C18 -178.28(7) . . . . ? C15 C12 C17 C18 -51.67(9) . . . . ? C10A C10 C4A C4 -179.62(7) . . . . ? C10A C10 C4A C9A 0.26(11) . . . . ? C3 C4 C4A C10 -179.74(8) . . . . ? C3 C4 C4A C9A 0.37(12) . . . . ? C9 C9A C4A C10 -1.62(11) . . . . ? C1 C9A C4A C10 179.35(7) . . . . ? C9 C9A C4A C4 178.26(7) . . . . ? C1 C9A C4A C4 -0.76(11) . . . . ? C4A C10 C10A C5 -178.54(7) . . . . ? C4A C10 C10A C8A 1.11(12) . . . . ? C6 C5 C10A C10 179.01(8) . . . . ? C6 C5 C10A C8A -0.64(12) . . . . ? C9A C9 C8A C8 177.11(7) . . . . ? C11 C9 C8A C8 -2.10(11) . . . . ? C9A C9 C8A C10A -0.29(11) . . . . ? C11 C9 C8A C10A -179.50(7) . . . . ? C7 C8 C8A C9 -178.18(8) . . . . ? C7 C8 C8A C10A -0.75(12) . . . . ? C10 C10A C8A C9 -1.10(11) . . . . ? C5 C10A C8A C9 178.56(7) . . . . ? C10 C10A C8A C8 -178.62(7) . . . . ? C5 C10A C8A C8 1.04(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.456 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.048 # Attachment 'cb17_0m_K.cif' data_cb17_0m _database_code_depnum_ccdc_archive 'CCDC 808565' #TrackingRef 'cb17_0m_K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 O2' _chemical_formula_weight 318.40 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 8.1422(7) _cell_length_b 9.8073(8) _cell_length_c 10.3190(9) _cell_angle_alpha 80.8542(13) _cell_angle_beta 87.0945(13) _cell_angle_gamma 86.9151(13) _cell_volume 811.61(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5221 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 31.15 _exptl_crystal_description 'square prism' _exptl_crystal_colour 'light-tinted yelloW' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9675 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 16115 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4018 _reflns_number_gt 3243 _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^)+(0.0684P)^2^+0.1135P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4018 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 0.02979(13) 0.69734(11) -0.04220(12) 0.0174(2) Uani 1 1 d . . . H1 H 0.0894 0.6243 0.0098 0.021 Uiso 1 1 calc R . . C2 C 0.03998(13) 0.70753(12) -0.17494(12) 0.0194(2) Uani 1 1 d . . . H2 H 0.1056 0.6411 -0.2145 0.023 Uiso 1 1 calc R . . C3 C -0.04629(13) 0.81637(12) -0.25581(12) 0.0196(2) Uani 1 1 d . . . H3 H -0.0357 0.8236 -0.3487 0.024 Uiso 1 1 calc R . . C4 C -0.14405(13) 0.91017(11) -0.20003(12) 0.0178(2) Uani 1 1 d . . . H4 H -0.2019 0.9821 -0.2547 0.021 Uiso 1 1 calc R . . C4A C -0.16088(12) 0.90202(11) -0.06091(11) 0.0149(2) Uani 1 1 d . . . C5 C -0.38036(13) 1.08715(11) 0.19359(12) 0.0185(2) Uani 1 1 d . . . H5 H -0.4431 1.1565 0.1398 0.022 Uiso 1 1 calc R . . C6 C -0.38998(13) 1.08225(12) 0.32574(13) 0.0207(3) Uani 1 1 d . . . H6 H -0.4582 1.1485 0.3635 0.025 Uiso 1 1 calc R . . C7 C -0.29872(14) 0.97864(12) 0.40812(12) 0.0204(3) Uani 1 1 d . . . H7 H -0.3059 0.9764 0.5006 0.024 Uiso 1 1 calc R . . C8 C -0.20074(13) 0.88216(11) 0.35567(12) 0.0176(2) Uani 1 1 d . . . H8 H -0.1417 0.8127 0.4122 0.021 Uiso 1 1 calc R . . C8A C -0.18571(12) 0.88422(10) 0.21693(11) 0.0143(2) Uani 1 1 d . . . C9 C -0.08340(12) 0.78900(11) 0.15758(11) 0.0141(2) Uani 1 1 d . . . C9A C -0.06953(12) 0.79496(10) 0.02113(11) 0.0143(2) Uani 1 1 d . . . C10 C -0.26264(12) 0.99613(11) -0.00194(12) 0.0162(2) Uani 1 1 d . . . H10 H -0.3235 1.0665 -0.0560 0.019 Uiso 1 1 calc R . . C10A C -0.27720(12) 0.98960(11) 0.13353(12) 0.0152(2) Uani 1 1 d . . . C11 C 0.00879(12) 0.67935(11) 0.24798(11) 0.0153(2) Uani 1 1 d . . . O1 O -0.05717(9) 0.58855(8) 0.32162(9) 0.0217(2) Uani 1 1 d . . . O2 O 0.17071(9) 0.70034(7) 0.23819(8) 0.01490(18) Uani 1 1 d . . . C12 C 0.28396(13) 0.62818(11) 0.33852(11) 0.0164(2) Uani 1 1 d . . . C13 C 0.29153(13) 0.47145(11) 0.34218(12) 0.0193(2) Uani 1 1 d . . . H13A H 0.3613 0.4279 0.4147 0.023 Uiso 1 1 calc R . . H13B H 0.1793 0.4372 0.3614 0.023 Uiso 1 1 calc R . . C14 C 0.35989(13) 0.42679(11) 0.21440(12) 0.0198(3) Uani 1 1 d . . . H14A H 0.2822 0.4586 0.1439 0.024 Uiso 1 1 calc R . . H14B H 0.3709 0.3246 0.2257 0.024 Uiso 1 1 calc R . . C15 C 0.52731(13) 0.48664(12) 0.17462(12) 0.0209(3) Uani 1 1 d . . . H15A H 0.6073 0.4501 0.2422 0.025 Uiso 1 1 calc R . . H15B H 0.5681 0.4586 0.0903 0.025 Uiso 1 1 calc R . . C16 C 0.51267(13) 0.64389(12) 0.16012(12) 0.0197(2) Uani 1 1 d . . . H16A H 0.6217 0.6823 0.1346 0.024 Uiso 1 1 calc R . . H16B H 0.4362 0.6806 0.0900 0.024 Uiso 1 1 calc R . . C17 C 0.44912(13) 0.68848(12) 0.28917(12) 0.0187(2) Uani 1 1 d . . . H17A H 0.4369 0.7906 0.2770 0.022 Uiso 1 1 calc R . . H17B H 0.5314 0.6588 0.3567 0.022 Uiso 1 1 calc R . . C18 C 0.22867(15) 0.66883(12) 0.47056(12) 0.0226(3) Uani 1 1 d . . . H18A H 0.2142 0.7697 0.4615 0.034 Uiso 1 1 calc R . . H18B H 0.3121 0.6360 0.5349 0.034 Uiso 1 1 calc R . . H18C H 0.1240 0.6270 0.5004 0.034 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 C1 0.0144(5) 0.0169(5) 0.0221(6) -0.0070(4) 0.0008(4) -0.0011(4) C2 0.0165(5) 0.0222(5) 0.0214(6) -0.0102(5) 0.0022(4) -0.0017(4) C3 0.0204(5) 0.0245(6) 0.0155(6) -0.0074(5) 0.0023(4) -0.0058(4) C4 0.0183(5) 0.0195(5) 0.0161(6) -0.0035(4) -0.0008(4) -0.0032(4) C4A 0.0136(5) 0.0154(5) 0.0164(6) -0.0039(4) 0.0010(4) -0.0040(4) C5 0.0164(5) 0.0165(5) 0.0230(7) -0.0048(4) 0.0013(4) 0.0004(4) C6 0.0191(5) 0.0203(5) 0.0240(7) -0.0092(5) 0.0052(5) -0.0009(4) C7 0.0215(5) 0.0244(6) 0.0166(6) -0.0077(5) 0.0037(4) -0.0043(4) C8 0.0176(5) 0.0185(5) 0.0172(6) -0.0041(4) 0.0008(4) -0.0027(4) C8A 0.0122(5) 0.0149(5) 0.0164(6) -0.0038(4) 0.0003(4) -0.0034(4) C9 0.0116(4) 0.0139(5) 0.0171(6) -0.0028(4) 0.0001(4) -0.0029(4) C9A 0.0114(4) 0.0143(5) 0.0179(6) -0.0046(4) 0.0015(4) -0.0037(4) C10 0.0149(5) 0.0151(5) 0.0188(6) -0.0029(4) -0.0007(4) -0.0009(4) C10A 0.0126(5) 0.0150(5) 0.0184(6) -0.0046(4) 0.0016(4) -0.0024(4) C11 0.0151(5) 0.0156(5) 0.0160(6) -0.0058(4) 0.0005(4) -0.0008(4) O1 0.0188(4) 0.0189(4) 0.0256(5) 0.0020(3) 0.0027(3) -0.0028(3) O2 0.0129(3) 0.0161(4) 0.0152(4) -0.0007(3) -0.0008(3) -0.0008(3) C12 0.0163(5) 0.0184(5) 0.0143(6) -0.0017(4) -0.0031(4) 0.0008(4) C13 0.0184(5) 0.0168(5) 0.0212(7) 0.0003(4) 0.0004(4) 0.0014(4) C14 0.0184(5) 0.0165(5) 0.0247(7) -0.0051(5) 0.0001(4) 0.0016(4) C15 0.0159(5) 0.0260(6) 0.0206(6) -0.0050(5) -0.0012(4) 0.0035(4) C16 0.0137(5) 0.0245(6) 0.0211(7) -0.0037(5) 0.0007(4) -0.0034(4) C17 0.0155(5) 0.0211(5) 0.0204(6) -0.0048(5) -0.0034(4) -0.0022(4) C18 0.0252(6) 0.0265(6) 0.0167(6) -0.0056(5) -0.0014(5) 0.0007(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 C2 1.3561(17) . ? C1 C9A 1.4351(14) . ? C1 H1 0.9500 . ? C2 C3 1.4230(17) . ? C2 H2 0.9500 . ? C3 C4 1.3617(15) . ? C3 H3 0.9500 . ? C4 C4A 1.4250(16) . ? C4 H4 0.9500 . ? C4A C10 1.3978(14) . ? C4A C9A 1.4386(15) . ? C5 C6 1.3553(17) . ? C5 C10A 1.4333(14) . ? C5 H5 0.9500 . ? C6 C7 1.4197(17) . ? C6 H6 0.9500 . ? C7 C8 1.3647(15) . ? C7 H7 0.9500 . ? C8 C8A 1.4277(16) . ? C8 H8 0.9500 . ? C8A C9 1.4098(14) . ? C8A C10A 1.4363(15) . ? C9 C9A 1.3990(16) . ? C9 C11 1.5017(15) . ? C10 C10A 1.3885(16) . ? C10 H10 0.9500 . ? C11 O1 1.2058(14) . ? C11 O2 1.3415(12) . ? O2 C12 1.4888(13) . ? C12 C18 1.5196(16) . ? C12 C17 1.5290(15) . ? C12 C13 1.5295(15) . ? C13 C14 1.5243(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5245(16) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5243(16) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5241(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 121.11(10) . . ? C2 C1 H1 119.4 . . ? C9A C1 H1 119.4 . . ? C1 C2 C3 120.94(10) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 120.00(11) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 120.99(11) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C10 C4A C4 121.76(10) . . ? C10 C4A C9A 119.05(10) . . ? C4 C4A C9A 119.19(9) . . ? C6 C5 C10A 121.17(11) . . ? C6 C5 H5 119.4 . . ? C10A C5 H5 119.4 . . ? C5 C6 C7 120.39(10) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.60(11) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 120.89(11) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C9 C8A C8 123.16(10) . . ? C9 C8A C10A 118.33(10) . . ? C8 C8A C10A 118.50(9) . . ? C9A C9 C8A 121.79(10) . . ? C9A C9 C11 121.40(9) . . ? C8A C9 C11 116.80(10) . . ? C9 C9A C1 123.19(10) . . ? C9 C9A C4A 119.10(9) . . ? C1 C9A C4A 117.71(10) . . ? C10A C10 C4A 121.82(10) . . ? C10A C10 H10 119.1 . . ? C4A C10 H10 119.1 . . ? C10 C10A C5 121.66(10) . . ? C10 C10A C8A 119.90(9) . . ? C5 C10A C8A 118.43(10) . . ? O1 C11 O2 125.72(10) . . ? O1 C11 C9 123.52(9) . . ? O2 C11 C9 110.71(9) . . ? C11 O2 C12 121.22(8) . . ? O2 C12 C18 108.10(8) . . ? O2 C12 C17 102.01(9) . . ? C18 C12 C17 111.42(9) . . ? O2 C12 C13 112.00(9) . . ? C18 C12 C13 112.18(10) . . ? C17 C12 C13 110.67(9) . . ? C14 C13 C12 113.42(10) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 110.96(9) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C14 109.90(8) . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 110.22(10) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C12 112.89(9) . . ? C16 C17 H17A 109.0 . . ? C12 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? C12 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C12 C18 H18A 109.5 . . ? C12 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C12 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C9A C1 C2 C3 0.67(16) . . . . ? C1 C2 C3 C4 -1.66(17) . . . . ? C2 C3 C4 C4A 0.48(17) . . . . ? C3 C4 C4A C10 -179.00(10) . . . . ? C3 C4 C4A C9A 1.62(16) . . . . ? C10A C5 C6 C7 -0.69(17) . . . . ? C5 C6 C7 C8 -0.33(17) . . . . ? C6 C7 C8 C8A 0.93(17) . . . . ? C7 C8 C8A C9 178.51(10) . . . . ? C7 C8 C8A C10A -0.51(15) . . . . ? C8 C8A C9 C9A -179.07(9) . . . . ? C10A C8A C9 C9A -0.06(15) . . . . ? C8 C8A C9 C11 1.67(15) . . . . ? C10A C8A C9 C11 -179.31(9) . . . . ? C8A C9 C9A C1 -178.18(9) . . . . ? C11 C9 C9A C1 1.05(15) . . . . ? C8A C9 C9A C4A 0.65(15) . . . . ? C11 C9 C9A C4A 179.87(9) . . . . ? C2 C1 C9A C9 -179.75(10) . . . . ? C2 C1 C9A C4A 1.41(15) . . . . ? C10 C4A C9A C9 -0.81(15) . . . . ? C4 C4A C9A C9 178.59(9) . . . . ? C10 C4A C9A C1 178.08(9) . . . . ? C4 C4A C9A C1 -2.52(14) . . . . ? C4 C4A C10 C10A -178.99(9) . . . . ? C9A C4A C10 C10A 0.39(16) . . . . ? C4A C10 C10A C5 179.35(10) . . . . ? C4A C10 C10A C8A 0.21(16) . . . . ? C6 C5 C10A C10 -178.07(10) . . . . ? C6 C5 C10A C8A 1.08(16) . . . . ? C9 C8A C10A C10 -0.38(15) . . . . ? C8 C8A C10A C10 178.68(9) . . . . ? C9 C8A C10A C5 -179.54(9) . . . . ? C8 C8A C10A C5 -0.48(15) . . . . ? C9A C9 C11 O1 -112.29(12) . . . . ? C8A C9 C11 O1 66.97(14) . . . . ? C9A C9 C11 O2 70.00(12) . . . . ? C8A C9 C11 O2 -110.74(10) . . . . ? O1 C11 O2 C12 -12.56(16) . . . . ? C9 C11 O2 C12 165.09(8) . . . . ? C11 O2 C12 C18 -60.25(12) . . . . ? C11 O2 C12 C17 -177.79(8) . . . . ? C11 O2 C12 C13 63.84(12) . . . . ? O2 C12 C13 C14 62.92(11) . . . . ? C18 C12 C13 C14 -175.31(9) . . . . ? C17 C12 C13 C14 -50.18(13) . . . . ? C12 C13 C14 C15 54.12(13) . . . . ? C13 C14 C15 C16 -57.78(13) . . . . ? C14 C15 C16 C17 59.05(12) . . . . ? C15 C16 C17 C12 -56.81(12) . . . . ? O2 C12 C17 C16 -67.75(11) . . . . ? C18 C12 C17 C16 177.13(9) . . . . ? C13 C12 C17 C16 51.57(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.284 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.073 # Attachment 'cb18_0m_C16.cif' data_cb18_0m _database_code_depnum_ccdc_archive 'CCDC 808566' #TrackingRef 'cb18_0m_C16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H42 O2' _chemical_formula_weight 446.65 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 6.9024(4) _cell_length_b 9.0519(6) _cell_length_c 20.6141(13) _cell_angle_alpha 87.7209(10) _cell_angle_beta 82.2444(10) _cell_angle_gamma 82.4091(10) _cell_volume 1264.68(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6839 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 31.38 _exptl_crystal_description 'thin plate frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9624 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 26928 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.70 _reflns_number_total 6537 _reflns_number_gt 4983 _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^)+(0.0661P)^2^+0.1634P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6537 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 -0.18481(14) 0.70475(11) 0.00561(5) 0.0190(2) Uani 1 1 d . . . H1 H -0.1799 0.6327 0.0403 0.023 Uiso 1 1 calc R . . C2 C -0.15332(15) 0.65909(12) -0.05744(5) 0.0218(2) Uani 1 1 d . . . H2 H -0.1272 0.5556 -0.0663 0.026 Uiso 1 1 calc R . . C3 C -0.15907(15) 0.76480(12) -0.11024(5) 0.0223(2) Uani 1 1 d . . . H3 H -0.1370 0.7315 -0.1541 0.027 Uiso 1 1 calc R . . C4 C -0.19590(14) 0.91288(12) -0.09843(5) 0.0200(2) Uani 1 1 d . . . H4 H -0.1985 0.9823 -0.1342 0.024 Uiso 1 1 calc R . . C4A C -0.23090(13) 0.96614(11) -0.03304(5) 0.0164(2) Uani 1 1 d . . . C5 C -0.34832(15) 1.32457(11) 0.05809(5) 0.0209(2) Uani 1 1 d . . . H5 H -0.3509 1.3958 0.0230 0.025 Uiso 1 1 calc R . . C6 C -0.38323(15) 1.37212(12) 0.12074(6) 0.0236(2) Uani 1 1 d . . . H6 H -0.4092 1.4758 0.1291 0.028 Uiso 1 1 calc R . . C7 C -0.38089(15) 1.26697(12) 0.17375(5) 0.0233(2) Uani 1 1 d . . . H7 H -0.4058 1.3011 0.2174 0.028 Uiso 1 1 calc R . . C8 C -0.34357(14) 1.11845(12) 0.16276(5) 0.0197(2) Uani 1 1 d . . . H8 H -0.3434 1.0500 0.1989 0.024 Uiso 1 1 calc R . . C8A C -0.30464(13) 1.06369(11) 0.09776(5) 0.0159(2) Uani 1 1 d . . . C9 C -0.26205(13) 0.91146(11) 0.08444(5) 0.0156(2) Uani 1 1 d . . . C9A C -0.22522(13) 0.85953(11) 0.02031(5) 0.0156(2) Uani 1 1 d . . . C10 C -0.27093(14) 1.11793(11) -0.01991(5) 0.0175(2) Uani 1 1 d . . . H10 H -0.2732 1.1880 -0.0554 0.021 Uiso 1 1 calc R . . C10A C -0.30780(13) 1.16959(11) 0.04401(5) 0.0169(2) Uani 1 1 d . . . C11 C -0.25899(14) 0.80227(11) 0.14084(5) 0.0174(2) Uani 1 1 d . . . O1 O -0.40083(11) 0.75946(10) 0.17190(4) 0.0339(2) Uani 1 1 d . . . O2 O -0.07467(10) 0.75790(9) 0.15329(4) 0.02364(18) Uani 1 1 d . . . C12 C -0.05238(15) 0.65701(12) 0.20929(5) 0.0223(2) Uani 1 1 d . . . H12A H -0.0833 0.5570 0.1997 0.027 Uiso 1 1 calc R . . H12B H -0.1425 0.6953 0.2482 0.027 Uiso 1 1 calc R . . C13 C 0.15955(15) 0.64866(12) 0.22160(5) 0.0208(2) Uani 1 1 d . . . H13A H 0.1904 0.7507 0.2274 0.025 Uiso 1 1 calc R . . H13B H 0.2468 0.6067 0.1828 0.025 Uiso 1 1 calc R . . C14 C 0.20191(15) 0.55319(12) 0.28179(5) 0.0204(2) Uani 1 1 d . . . H14A H 0.1821 0.4491 0.2744 0.024 Uiso 1 1 calc R . . H14B H 0.1072 0.5900 0.3199 0.024 Uiso 1 1 calc R . . C15 C 0.41138(14) 0.55555(11) 0.29735(5) 0.0170(2) Uani 1 1 d . . . H15A H 0.5053 0.5245 0.2582 0.020 Uiso 1 1 calc R . . H15B H 0.4283 0.6591 0.3068 0.020 Uiso 1 1 calc R . . C16 C 0.46269(14) 0.45479(11) 0.35512(5) 0.0185(2) Uani 1 1 d . . . H16A H 0.4342 0.3529 0.3476 0.022 Uiso 1 1 calc R . . H16B H 0.3774 0.4916 0.3952 0.022 Uiso 1 1 calc R . . C17 C 0.67782(14) 0.44750(11) 0.36608(5) 0.0172(2) Uani 1 1 d . . . H17A H 0.7627 0.4046 0.3270 0.021 Uiso 1 1 calc R . . H17B H 0.7085 0.5501 0.3706 0.021 Uiso 1 1 calc R . . C18 C 0.72759(14) 0.35487(11) 0.42634(5) 0.0178(2) Uani 1 1 d . . . H18A H 0.6936 0.2530 0.4223 0.021 Uiso 1 1 calc R . . H18B H 0.6451 0.3993 0.4655 0.021 Uiso 1 1 calc R . . C19 C 0.94407(14) 0.34417(11) 0.43639(5) 0.0173(2) Uani 1 1 d . . . H19A H 1.0265 0.2983 0.3975 0.021 Uiso 1 1 calc R . . H19B H 0.9787 0.4460 0.4398 0.021 Uiso 1 1 calc R . . C20 C 0.99231(14) 0.25319(11) 0.49730(5) 0.0177(2) Uani 1 1 d . . . H20A H 0.9559 0.1518 0.4942 0.021 Uiso 1 1 calc R . . H20B H 0.9111 0.2999 0.5362 0.021 Uiso 1 1 calc R . . C21 C 1.20909(14) 0.24055(11) 0.50694(5) 0.0173(2) Uani 1 1 d . . . H21A H 1.2903 0.1933 0.4681 0.021 Uiso 1 1 calc R . . H21B H 1.2458 0.3419 0.5099 0.021 Uiso 1 1 calc R . . C22 C 1.25656(14) 0.15021(11) 0.56805(5) 0.0177(2) Uani 1 1 d . . . H22A H 1.2180 0.0493 0.5654 0.021 Uiso 1 1 calc R . . H22B H 1.1767 0.1983 0.6069 0.021 Uiso 1 1 calc R . . C23 C 1.47359(14) 0.13543(11) 0.57737(5) 0.0175(2) Uani 1 1 d . . . H23A H 1.5127 0.2364 0.5793 0.021 Uiso 1 1 calc R . . H23B H 1.5533 0.0859 0.5388 0.021 Uiso 1 1 calc R . . C24 C 1.52092(14) 0.04724(11) 0.63903(5) 0.0182(2) Uani 1 1 d . . . H24A H 1.4434 0.0978 0.6777 0.022 Uiso 1 1 calc R . . H24B H 1.4797 -0.0531 0.6376 0.022 Uiso 1 1 calc R . . C25 C 1.73872(14) 0.03059(11) 0.64725(5) 0.0175(2) Uani 1 1 d . . . H25A H 1.8160 -0.0209 0.6088 0.021 Uiso 1 1 calc R . . H25B H 1.7801 0.1310 0.6482 0.021 Uiso 1 1 calc R . . C26 C 1.78692(15) -0.05595(12) 0.70910(5) 0.0211(2) Uani 1 1 d . . . H26A H 1.7472 -0.1569 0.7081 0.025 Uiso 1 1 calc R . . H26B H 1.7092 -0.0051 0.7477 0.025 Uiso 1 1 calc R . . C27 C 2.00492(15) -0.07006(13) 0.71668(5) 0.0247(2) Uani 1 1 d . . . H27A H 2.0828 -0.1198 0.6785 0.037 Uiso 1 1 calc R . . H27B H 2.0287 -0.1289 0.7564 0.037 Uiso 1 1 calc R . . H27C H 2.0437 0.0294 0.7200 0.037 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 C1 0.0153(5) 0.0190(5) 0.0232(5) 0.0020(4) -0.0044(4) -0.0026(4) C2 0.0180(5) 0.0206(5) 0.0268(5) -0.0033(4) -0.0023(4) -0.0020(4) C3 0.0191(5) 0.0301(6) 0.0181(5) -0.0037(4) -0.0015(4) -0.0051(4) C4 0.0171(5) 0.0271(5) 0.0164(5) 0.0026(4) -0.0027(4) -0.0049(4) C4A 0.0113(4) 0.0209(5) 0.0174(5) 0.0024(4) -0.0028(4) -0.0033(4) C5 0.0162(5) 0.0185(5) 0.0282(5) 0.0037(4) -0.0042(4) -0.0029(4) C6 0.0189(5) 0.0188(5) 0.0331(6) -0.0044(4) -0.0029(4) -0.0022(4) C7 0.0205(5) 0.0268(5) 0.0231(5) -0.0058(4) -0.0038(4) -0.0032(4) C8 0.0169(5) 0.0243(5) 0.0185(5) 0.0010(4) -0.0042(4) -0.0035(4) C8A 0.0116(4) 0.0186(5) 0.0179(5) 0.0024(4) -0.0039(3) -0.0028(3) C9 0.0115(4) 0.0192(5) 0.0167(5) 0.0033(4) -0.0039(3) -0.0033(3) C9A 0.0110(4) 0.0189(5) 0.0175(5) 0.0015(4) -0.0036(3) -0.0025(3) C10 0.0155(4) 0.0185(5) 0.0190(5) 0.0057(4) -0.0046(4) -0.0039(4) C10A 0.0118(4) 0.0181(5) 0.0208(5) 0.0032(4) -0.0030(4) -0.0029(4) C11 0.0165(5) 0.0177(5) 0.0186(5) 0.0014(4) -0.0049(4) -0.0020(4) O1 0.0180(4) 0.0449(5) 0.0385(5) 0.0245(4) -0.0055(3) -0.0081(3) O2 0.0160(4) 0.0318(4) 0.0226(4) 0.0146(3) -0.0058(3) -0.0023(3) C12 0.0198(5) 0.0266(5) 0.0207(5) 0.0112(4) -0.0067(4) -0.0033(4) C13 0.0167(5) 0.0245(5) 0.0211(5) 0.0078(4) -0.0058(4) -0.0013(4) C14 0.0186(5) 0.0221(5) 0.0211(5) 0.0073(4) -0.0069(4) -0.0030(4) C15 0.0171(5) 0.0166(5) 0.0175(5) 0.0028(4) -0.0054(4) -0.0010(4) C16 0.0171(5) 0.0198(5) 0.0189(5) 0.0049(4) -0.0058(4) -0.0024(4) C17 0.0157(5) 0.0183(5) 0.0179(5) 0.0032(4) -0.0048(4) -0.0019(4) C18 0.0161(5) 0.0193(5) 0.0185(5) 0.0033(4) -0.0055(4) -0.0019(4) C19 0.0162(5) 0.0179(5) 0.0183(5) 0.0019(4) -0.0053(4) -0.0011(4) C20 0.0160(5) 0.0193(5) 0.0186(5) 0.0029(4) -0.0058(4) -0.0024(4) C21 0.0161(5) 0.0189(5) 0.0172(5) 0.0018(4) -0.0048(4) -0.0015(4) C22 0.0159(5) 0.0192(5) 0.0188(5) 0.0023(4) -0.0056(4) -0.0026(4) C23 0.0160(5) 0.0193(5) 0.0174(5) 0.0013(4) -0.0048(4) -0.0010(4) C24 0.0166(5) 0.0201(5) 0.0186(5) 0.0020(4) -0.0057(4) -0.0027(4) C25 0.0161(5) 0.0199(5) 0.0167(5) 0.0008(4) -0.0046(4) -0.0009(4) C26 0.0185(5) 0.0260(5) 0.0198(5) 0.0044(4) -0.0068(4) -0.0039(4) C27 0.0202(5) 0.0323(6) 0.0226(5) 0.0042(4) -0.0082(4) -0.0020(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 C2 1.3601(15) . ? C1 C9A 1.4284(14) . ? C1 H1 0.9500 . ? C2 C3 1.4214(15) . ? C2 H2 0.9500 . ? C3 C4 1.3564(15) . ? C3 H3 0.9500 . ? C4 C4A 1.4285(14) . ? C4 H4 0.9500 . ? C4A C10 1.3951(14) . ? C4A C9A 1.4351(13) . ? C5 C6 1.3578(15) . ? C5 C10A 1.4274(14) . ? C5 H5 0.9500 . ? C6 C7 1.4206(15) . ? C6 H6 0.9500 . ? C7 C8 1.3572(15) . ? C7 H7 0.9500 . ? C8 C8A 1.4261(14) . ? C8 H8 0.9500 . ? C8A C9 1.4007(14) . ? C8A C10A 1.4365(13) . ? C9 C9A 1.4001(13) . ? C9 C11 1.4962(13) . ? C10 C10A 1.3953(14) . ? C10 H10 0.9500 . ? C11 O1 1.1959(12) . ? C11 O2 1.3382(11) . ? O2 C12 1.4551(11) . ? C12 C13 1.5098(14) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5225(13) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5256(13) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5224(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5244(13) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5234(13) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.5260(13) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.5244(13) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.5247(13) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.5237(13) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.5237(13) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5238(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.5226(13) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.5217(13) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.5219(14) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.89(9) . . ? C2 C1 H1 119.6 . . ? C9A C1 H1 119.6 . . ? C1 C2 C3 120.58(10) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.41(9) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C4A 121.04(9) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C10 C4A C4 121.87(9) . . ? C10 C4A C9A 119.52(9) . . ? C4 C4A C9A 118.61(9) . . ? C6 C5 C10A 121.21(10) . . ? C6 C5 H5 119.4 . . ? C10A C5 H5 119.4 . . ? C5 C6 C7 120.05(10) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.85(10) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 120.96(9) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C9 C8A C8 122.64(9) . . ? C9 C8A C10A 118.98(9) . . ? C8 C8A C10A 118.38(9) . . ? C9A C9 C8A 121.91(9) . . ? C9A C9 C11 119.61(9) . . ? C8A C9 C11 118.47(9) . . ? C9 C9A C1 122.85(9) . . ? C9 C9A C4A 118.68(9) . . ? C1 C9A C4A 118.47(9) . . ? C4A C10 C10A 121.77(9) . . ? C4A C10 H10 119.1 . . ? C10A C10 H10 119.1 . . ? C10 C10A C5 122.31(9) . . ? C10 C10A C8A 119.14(9) . . ? C5 C10A C8A 118.55(9) . . ? O1 C11 O2 123.22(9) . . ? O1 C11 C9 125.49(9) . . ? O2 C11 C9 111.29(8) . . ? C11 O2 C12 116.64(7) . . ? O2 C12 C13 106.65(8) . . ? O2 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? O2 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12 C13 C14 112.52(8) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 112.34(8) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 113.83(8) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 113.12(8) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.53(8) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C19 113.59(8) . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 113.33(8) . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? C18 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 113.43(8) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 113.29(8) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 113.48(8) . . ? C21 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C22 C23 C24 113.60(8) . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23B 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C25 C24 C23 113.21(8) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C26 C25 C24 113.54(8) . . ? C26 C25 H25A 108.9 . . ? C24 C25 H25A 108.9 . . ? C26 C25 H25B 108.9 . . ? C24 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? C25 C26 C27 112.68(8) . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C9A C1 C2 C3 0.28(15) . . . . ? C1 C2 C3 C4 0.07(15) . . . . ? C2 C3 C4 C4A -0.40(15) . . . . ? C3 C4 C4A C10 -179.36(9) . . . . ? C3 C4 C4A C9A 0.37(14) . . . . ? C10A C5 C6 C7 -0.34(15) . . . . ? C5 C6 C7 C8 0.16(16) . . . . ? C6 C7 C8 C8A 0.33(15) . . . . ? C7 C8 C8A C9 178.83(9) . . . . ? C7 C8 C8A C10A -0.62(14) . . . . ? C8 C8A C9 C9A 179.64(9) . . . . ? C10A C8A C9 C9A -0.90(14) . . . . ? C8 C8A C9 C11 0.49(14) . . . . ? C10A C8A C9 C11 179.94(8) . . . . ? C8A C9 C9A C1 -178.91(9) . . . . ? C11 C9 C9A C1 0.24(14) . . . . ? C8A C9 C9A C4A 0.22(14) . . . . ? C11 C9 C9A C4A 179.36(8) . . . . ? C2 C1 C9A C9 178.81(9) . . . . ? C2 C1 C9A C4A -0.31(14) . . . . ? C10 C4A C9A C9 0.56(13) . . . . ? C4 C4A C9A C9 -179.17(8) . . . . ? C10 C4A C9A C1 179.72(8) . . . . ? C4 C4A C9A C1 -0.01(13) . . . . ? C4 C4A C10 C10A 179.09(9) . . . . ? C9A C4A C10 C10A -0.64(14) . . . . ? C4A C10 C10A C5 179.80(9) . . . . ? C4A C10 C10A C8A -0.06(14) . . . . ? C6 C5 C10A C10 -179.82(9) . . . . ? C6 C5 C10A C8A 0.03(14) . . . . ? C9 C8A C10A C10 0.82(13) . . . . ? C8 C8A C10A C10 -179.70(8) . . . . ? C9 C8A C10A C5 -179.04(8) . . . . ? C8 C8A C10A C5 0.44(13) . . . . ? C9A C9 C11 O1 -98.74(13) . . . . ? C8A C9 C11 O1 80.43(14) . . . . ? C9A C9 C11 O2 81.88(11) . . . . ? C8A C9 C11 O2 -98.94(10) . . . . ? O1 C11 O2 C12 -2.38(15) . . . . ? C9 C11 O2 C12 177.02(8) . . . . ? C11 O2 C12 C13 -168.61(9) . . . . ? O2 C12 C13 C14 176.67(9) . . . . ? C12 C13 C14 C15 -175.23(9) . . . . ? C13 C14 C15 C16 -176.94(9) . . . . ? C14 C15 C16 C17 174.73(8) . . . . ? C15 C16 C17 C18 176.33(8) . . . . ? C16 C17 C18 C19 178.52(8) . . . . ? C17 C18 C19 C20 179.18(8) . . . . ? C18 C19 C20 C21 179.21(8) . . . . ? C19 C20 C21 C22 179.71(8) . . . . ? C20 C21 C22 C23 179.20(8) . . . . ? C21 C22 C23 C24 179.08(8) . . . . ? C22 C23 C24 C25 178.92(8) . . . . ? C23 C24 C25 C26 179.38(8) . . . . ? C24 C25 C26 C27 -179.47(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.351 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 # Attachment 'cb19_0m_AAE.cif' data_cb19_0m _database_code_depnum_ccdc_archive 'CCDC 808567' #TrackingRef 'cb19_0m_AAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 O2' _chemical_formula_weight 356.44 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.3689(7) _cell_length_b 6.3517(2) _cell_length_c 17.6297(7) _cell_angle_alpha 90.00 _cell_angle_beta 113.1194(5) _cell_angle_gamma 90.00 _cell_volume 1788.74(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9986 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 31.22 _exptl_crystal_description 'needle frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9562 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 24919 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 29.13 _reflns_number_total 4822 _reflns_number_gt 4364 _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^)+(0.0610P)^2^+0.6599P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4822 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.51076(6) 0.56859(15) 0.24423(6) 0.01556(18) Uani 1 1 d . . . H1 H 0.5034 0.5829 0.1882 0.019 Uiso 1 1 calc R . . C2 C 0.55409(6) 0.40071(16) 0.28861(6) 0.01710(19) Uani 1 1 d . . . H2 H 0.5749 0.2971 0.2627 0.021 Uiso 1 1 calc R . . C3 C 0.56850(6) 0.37905(16) 0.37343(6) 0.01744(19) Uani 1 1 d . . . H3 H 0.5994 0.2623 0.4040 0.021 Uiso 1 1 calc R . . C4 C 0.53800(6) 0.52561(15) 0.41077(6) 0.01615(18) Uani 1 1 d . . . H4 H 0.5491 0.5116 0.4678 0.019 Uiso 1 1 calc R . . C4A C 0.48965(5) 0.69990(15) 0.36576(5) 0.01354(17) Uani 1 1 d . . . C5 C 0.36830(6) 1.15934(16) 0.39486(6) 0.01621(18) Uani 1 1 d . . . H5 H 0.3739 1.1377 0.4501 0.019 Uiso 1 1 calc R . . C6 C 0.32427(6) 1.32788(16) 0.35201(6) 0.01834(19) Uani 1 1 d . . . H6 H 0.2995 1.4229 0.3775 0.022 Uiso 1 1 calc R . . C7 C 0.31512(6) 1.36264(16) 0.26910(6) 0.01777(19) Uani 1 1 d . . . H7 H 0.2852 1.4823 0.2400 0.021 Uiso 1 1 calc R . . C8 C 0.34897(6) 1.22581(15) 0.23115(6) 0.01579(18) Uani 1 1 d . . . H8 H 0.3416 1.2504 0.1756 0.019 Uiso 1 1 calc R . . C8A C 0.39541(5) 1.04572(14) 0.27372(5) 0.01299(17) Uani 1 1 d . . . C9 C 0.42956(5) 0.89713(15) 0.23646(5) 0.01282(17) Uani 1 1 d . . . C9A C 0.47603(5) 0.72388(14) 0.28042(5) 0.01307(17) Uani 1 1 d . . . C10 C 0.45351(6) 0.84381(15) 0.40189(5) 0.01460(18) Uani 1 1 d . . . H10 H 0.4613 0.8252 0.4579 0.018 Uiso 1 1 calc R . . C10A C 0.40635(5) 1.01395(15) 0.35798(5) 0.01355(17) Uani 1 1 d . . . C11 C 0.41429(6) 0.92324(15) 0.14706(5) 0.01373(17) Uani 1 1 d . . . O1 O 0.44137(5) 1.06615(12) 0.11955(4) 0.01997(16) Uani 1 1 d . . . O2 O 0.36560(4) 0.76621(11) 0.10317(4) 0.01345(14) Uani 1 1 d . . . C12 C 0.34442(5) 0.74292(14) 0.01420(5) 0.01132(17) Uani 1 1 d . . . C13 C 0.42262(5) 0.72037(14) -0.00477(5) 0.01270(17) Uani 1 1 d . . . H13A H 0.4581 0.6043 0.0283 0.015 Uiso 1 1 calc R . . H13B H 0.4557 0.8521 0.0096 0.015 Uiso 1 1 calc R . . C14 C 0.39522(6) 0.67330(14) -0.09739(5) 0.01335(17) Uani 1 1 d . . . H14 H 0.4458 0.6592 -0.1108 0.016 Uiso 1 1 calc R . . C15 C 0.34485(6) 0.46824(14) -0.11917(6) 0.01453(18) Uani 1 1 d . . . H15A H 0.3798 0.3502 -0.0872 0.017 Uiso 1 1 calc R . . H15B H 0.3277 0.4373 -0.1786 0.017 Uiso 1 1 calc R . . C16 C 0.26688(6) 0.49086(14) -0.09888(5) 0.01438(18) Uani 1 1 d . . . H16 H 0.2340 0.3570 -0.1127 0.017 Uiso 1 1 calc R . . C17 C 0.21216(6) 0.67296(15) -0.14863(6) 0.01679(19) Uani 1 1 d . . . H17A H 0.1934 0.6439 -0.2084 0.020 Uiso 1 1 calc R . . H17B H 0.1620 0.6870 -0.1355 0.020 Uiso 1 1 calc R . . C18 C 0.26282(6) 0.87757(15) -0.12713(6) 0.01531(18) Uani 1 1 d . . . H18 H 0.2274 0.9960 -0.1601 0.018 Uiso 1 1 calc R . . C19 C 0.29020(6) 0.92488(14) -0.03462(5) 0.01413(17) Uani 1 1 d . . . H19A H 0.3224 1.0580 -0.0205 0.017 Uiso 1 1 calc R . . H19B H 0.2404 0.9404 -0.0209 0.017 Uiso 1 1 calc R . . C20 C 0.29479(6) 0.53739(14) -0.00648(5) 0.01384(17) Uani 1 1 d . . . H20A H 0.2451 0.5496 0.0077 0.017 Uiso 1 1 calc R . . H20B H 0.3301 0.4206 0.0262 0.017 Uiso 1 1 calc R . . C21 C 0.34058(6) 0.85449(15) -0.14756(5) 0.01535(18) Uani 1 1 d . . . H21A H 0.3232 0.8260 -0.2072 0.018 Uiso 1 1 calc R . . H21B H 0.3731 0.9872 -0.1344 0.018 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 C1 0.0146(4) 0.0187(4) 0.0142(4) -0.0034(3) 0.0065(3) -0.0007(3) C2 0.0146(4) 0.0178(4) 0.0202(4) -0.0038(3) 0.0081(3) -0.0001(3) C3 0.0156(4) 0.0162(4) 0.0206(4) 0.0015(3) 0.0072(3) 0.0009(3) C4 0.0158(4) 0.0180(4) 0.0148(4) 0.0014(3) 0.0062(3) -0.0005(3) C4A 0.0128(4) 0.0153(4) 0.0127(4) -0.0009(3) 0.0052(3) -0.0016(3) C5 0.0158(4) 0.0201(4) 0.0143(4) -0.0039(3) 0.0076(3) -0.0014(3) C6 0.0168(4) 0.0193(4) 0.0205(4) -0.0047(4) 0.0091(4) 0.0005(3) C7 0.0158(4) 0.0163(4) 0.0205(4) 0.0001(3) 0.0063(4) 0.0011(3) C8 0.0152(4) 0.0170(4) 0.0148(4) 0.0001(3) 0.0055(3) -0.0010(3) C8A 0.0121(4) 0.0144(4) 0.0127(4) -0.0020(3) 0.0050(3) -0.0021(3) C9 0.0126(4) 0.0154(4) 0.0107(4) -0.0022(3) 0.0048(3) -0.0023(3) C9A 0.0120(4) 0.0149(4) 0.0125(4) -0.0025(3) 0.0050(3) -0.0025(3) C10 0.0155(4) 0.0171(4) 0.0119(4) -0.0013(3) 0.0062(3) -0.0017(3) C10A 0.0128(4) 0.0153(4) 0.0133(4) -0.0030(3) 0.0059(3) -0.0024(3) C11 0.0134(4) 0.0156(4) 0.0122(4) -0.0021(3) 0.0052(3) -0.0002(3) O1 0.0263(4) 0.0194(3) 0.0161(3) -0.0029(3) 0.0103(3) -0.0078(3) O2 0.0156(3) 0.0153(3) 0.0094(3) -0.0018(2) 0.0048(2) -0.0028(2) C12 0.0130(4) 0.0125(4) 0.0083(3) -0.0015(3) 0.0039(3) -0.0005(3) C13 0.0119(4) 0.0143(4) 0.0116(4) -0.0004(3) 0.0043(3) 0.0003(3) C14 0.0151(4) 0.0138(4) 0.0122(4) -0.0006(3) 0.0065(3) 0.0010(3) C15 0.0177(4) 0.0125(4) 0.0131(4) -0.0019(3) 0.0057(3) 0.0019(3) C16 0.0156(4) 0.0128(4) 0.0138(4) -0.0028(3) 0.0048(3) -0.0015(3) C17 0.0146(4) 0.0188(4) 0.0136(4) -0.0030(3) 0.0019(3) 0.0017(3) C18 0.0172(4) 0.0142(4) 0.0119(4) 0.0001(3) 0.0029(3) 0.0047(3) C19 0.0157(4) 0.0131(4) 0.0128(4) -0.0014(3) 0.0046(3) 0.0031(3) C20 0.0154(4) 0.0134(4) 0.0131(4) -0.0016(3) 0.0059(3) -0.0024(3) C21 0.0218(4) 0.0132(4) 0.0117(4) 0.0012(3) 0.0072(3) 0.0017(3) _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 C2 1.3613(13) . ? C1 C9A 1.4304(12) . ? C1 H1 0.9500 . ? C2 C3 1.4226(13) . ? C2 H2 0.9500 . ? C3 C4 1.3618(13) . ? C3 H3 0.9500 . ? C4 C4A 1.4273(13) . ? C4 H4 0.9500 . ? C4A C10 1.3962(12) . ? C4A C9A 1.4363(12) . ? C5 C6 1.3594(14) . ? C5 C10A 1.4317(12) . ? C5 H5 0.9500 . ? C6 C7 1.4242(14) . ? C6 H6 0.9500 . ? C7 C8 1.3629(13) . ? C7 H7 0.9500 . ? C8 C8A 1.4307(13) . ? C8 H8 0.9500 . ? C8A C9 1.4072(12) . ? C8A C10A 1.4358(12) . ? C9 C9A 1.4042(12) . ? C9 C11 1.5012(12) . ? C10 C10A 1.3929(13) . ? C10 H10 0.9500 . ? C11 O1 1.2081(12) . ? C11 O2 1.3397(11) . ? O2 C12 1.4711(10) . ? C12 C19 1.5254(12) . ? C12 C20 1.5276(12) . ? C12 C13 1.5277(12) . ? C13 C14 1.5401(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5316(13) . ? C14 C21 1.5324(12) . ? C14 H14 1.0000 . ? C15 C16 1.5370(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5349(13) . ? C16 C20 1.5349(12) . ? C16 H16 1.0000 . ? C17 C18 1.5314(13) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C21 1.5353(13) . ? C18 C19 1.5387(12) . ? C18 H18 1.0000 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 121.24(8) . . ? C2 C1 H1 119.4 . . ? C9A C1 H1 119.4 . . ? C1 C2 C3 120.61(9) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.05(9) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 121.14(8) . . ? C3 C4 H4 119.4 . . ? C4A C4 H4 119.4 . . ? C10 C4A C4 121.73(8) . . ? C10 C4A C9A 119.33(8) . . ? C4 C4A C9A 118.92(8) . . ? C6 C5 C10A 120.99(8) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 120.27(9) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.61(9) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 121.02(9) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C9 C8A C8 123.05(8) . . ? C9 C8A C10A 118.68(8) . . ? C8 C8A C10A 118.26(8) . . ? C9A C9 C8A 121.61(8) . . ? C9A C9 C11 119.50(8) . . ? C8A C9 C11 118.88(8) . . ? C9 C9A C1 123.08(8) . . ? C9 C9A C4A 118.94(8) . . ? C1 C9A C4A 117.98(8) . . ? C10A C10 C4A 121.73(8) . . ? C10A C10 H10 119.1 . . ? C4A C10 H10 119.1 . . ? C10 C10A C5 121.57(8) . . ? C10 C10A C8A 119.61(8) . . ? C5 C10A C8A 118.82(8) . . ? O1 C11 O2 125.76(8) . . ? O1 C11 C9 124.63(8) . . ? O2 C11 C9 109.60(7) . . ? C11 O2 C12 121.84(7) . . ? O2 C12 C19 111.46(7) . . ? O2 C12 C20 102.82(7) . . ? C19 C12 C20 110.33(7) . . ? O2 C12 C13 111.78(7) . . ? C19 C12 C13 110.64(7) . . ? C20 C12 C13 109.55(7) . . ? C12 C13 C14 108.61(7) . . ? C12 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? C12 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C21 109.30(7) . . ? C15 C14 C13 109.83(7) . . ? C21 C14 C13 109.25(7) . . ? C15 C14 H14 109.5 . . ? C21 C14 H14 109.5 . . ? C13 C14 H14 109.5 . . ? C14 C15 C16 109.33(7) . . ? C14 C15 H15A 109.8 . . ? C16 C15 H15A 109.8 . . ? C14 C15 H15B 109.8 . . ? C16 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? C17 C16 C20 109.15(7) . . ? C17 C16 C15 109.99(7) . . ? C20 C16 C15 108.97(7) . . ? C17 C16 H16 109.6 . . ? C20 C16 H16 109.6 . . ? C15 C16 H16 109.6 . . ? C18 C17 C16 109.35(7) . . ? C18 C17 H17A 109.8 . . ? C16 C17 H17A 109.8 . . ? C18 C17 H17B 109.8 . . ? C16 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? C17 C18 C21 109.50(7) . . ? C17 C18 C19 109.67(8) . . ? C21 C18 C19 109.45(7) . . ? C17 C18 H18 109.4 . . ? C21 C18 H18 109.4 . . ? C19 C18 H18 109.4 . . ? C12 C19 C18 108.39(7) . . ? C12 C19 H19A 110.0 . . ? C18 C19 H19A 110.0 . . ? C12 C19 H19B 110.0 . . ? C18 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? C12 C20 C16 109.34(7) . . ? C12 C20 H20A 109.8 . . ? C16 C20 H20A 109.8 . . ? C12 C20 H20B 109.8 . . ? C16 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? C14 C21 C18 109.81(7) . . ? C14 C21 H21A 109.7 . . ? C18 C21 H21A 109.7 . . ? C14 C21 H21B 109.7 . . ? C18 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? 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 C9A C1 C2 C3 -2.17(14) . . . . ? C1 C2 C3 C4 0.79(14) . . . . ? C2 C3 C4 C4A 1.51(14) . . . . ? C3 C4 C4A C10 175.84(9) . . . . ? C3 C4 C4A C9A -2.39(14) . . . . ? C10A C5 C6 C7 0.08(14) . . . . ? C5 C6 C7 C8 1.20(15) . . . . ? C6 C7 C8 C8A -0.85(14) . . . . ? C7 C8 C8A C9 178.23(9) . . . . ? C7 C8 C8A C10A -0.72(13) . . . . ? C8 C8A C9 C9A 178.93(8) . . . . ? C10A C8A C9 C9A -2.12(13) . . . . ? C8 C8A C9 C11 -2.26(13) . . . . ? C10A C8A C9 C11 176.69(8) . . . . ? C8A C9 C9A C1 179.23(8) . . . . ? C11 C9 C9A C1 0.43(13) . . . . ? C8A C9 C9A C4A -0.74(13) . . . . ? C11 C9 C9A C4A -179.53(8) . . . . ? C2 C1 C9A C9 -178.73(9) . . . . ? C2 C1 C9A C4A 1.23(13) . . . . ? C10 C4A C9A C9 2.71(13) . . . . ? C4 C4A C9A C9 -179.02(8) . . . . ? C10 C4A C9A C1 -177.25(8) . . . . ? C4 C4A C9A C1 1.02(13) . . . . ? C4 C4A C10 C10A 179.97(8) . . . . ? C9A C4A C10 C10A -1.81(13) . . . . ? C4A C10 C10A C5 179.01(8) . . . . ? C4A C10 C10A C8A -1.08(13) . . . . ? C6 C5 C10A C10 178.26(9) . . . . ? C6 C5 C10A C8A -1.64(14) . . . . ? C9 C8A C10A C10 3.03(13) . . . . ? C8 C8A C10A C10 -177.96(8) . . . . ? C9 C8A C10A C5 -177.06(8) . . . . ? C8 C8A C10A C5 1.94(12) . . . . ? C9A C9 C11 O1 -114.82(11) . . . . ? C8A C9 C11 O1 66.35(12) . . . . ? C9A C9 C11 O2 65.94(10) . . . . ? C8A C9 C11 O2 -112.89(9) . . . . ? O1 C11 O2 C12 4.70(14) . . . . ? C9 C11 O2 C12 -176.08(7) . . . . ? C11 O2 C12 C19 -66.01(10) . . . . ? C11 O2 C12 C20 175.82(7) . . . . ? C11 O2 C12 C13 58.40(10) . . . . ? O2 C12 C13 C14 174.06(7) . . . . ? C19 C12 C13 C14 -61.08(9) . . . . ? C20 C12 C13 C14 60.77(9) . . . . ? C12 C13 C14 C15 -60.19(9) . . . . ? C12 C13 C14 C21 59.68(9) . . . . ? C21 C14 C15 C16 -59.81(9) . . . . ? C13 C14 C15 C16 60.03(9) . . . . ? C14 C15 C16 C17 59.79(9) . . . . ? C14 C15 C16 C20 -59.82(9) . . . . ? C20 C16 C17 C18 59.97(10) . . . . ? C15 C16 C17 C18 -59.54(9) . . . . ? C16 C17 C18 C21 59.38(9) . . . . ? C16 C17 C18 C19 -60.73(9) . . . . ? O2 C12 C19 C18 -173.93(7) . . . . ? C20 C12 C19 C18 -60.36(9) . . . . ? C13 C12 C19 C18 61.02(9) . . . . ? C17 C18 C19 C12 60.34(9) . . . . ? C21 C18 C19 C12 -59.80(9) . . . . ? O2 C12 C20 C16 179.48(7) . . . . ? C19 C12 C20 C16 60.50(9) . . . . ? C13 C12 C20 C16 -61.53(9) . . . . ? C17 C16 C20 C12 -59.57(9) . . . . ? C15 C16 C20 C12 60.57(9) . . . . ? C15 C14 C21 C18 60.25(9) . . . . ? C13 C14 C21 C18 -59.94(9) . . . . ? C17 C18 C21 C14 -60.10(9) . . . . ? C19 C18 C21 C14 60.15(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.423 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.055 # Attachment 'cb20_0m_CHAE.cif' data_cb20_0m _database_code_depnum_ccdc_archive 'CCDC 808568' #TrackingRef 'cb20_0m_CHAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O2' _chemical_formula_weight 304.37 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 11.2996(5) _cell_length_b 12.3091(6) _cell_length_c 12.3511(6) _cell_angle_alpha 88.7806(7) _cell_angle_beta 74.3156(7) _cell_angle_gamma 75.1626(7) _cell_volume 1596.65(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8903 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 30.31 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 28959 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 29.13 _reflns_number_total 8567 _reflns_number_gt 6783 _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^)+(0.0493P)^2^+0.6035P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8567 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.62488(11) 0.63544(10) 0.12072(11) 0.0215(2) Uani 1 1 d . . . H1 H 0.5912 0.6408 0.2003 0.026 Uiso 1 1 calc R . . C2 C 0.54973(12) 0.62490(11) 0.05430(12) 0.0252(3) Uani 1 1 d . . . H2 H 0.4640 0.6236 0.0880 0.030 Uiso 1 1 calc R . . C3 C 0.59790(12) 0.61585(11) -0.06491(11) 0.0255(3) Uani 1 1 d . . . H3 H 0.5442 0.6092 -0.1104 0.031 Uiso 1 1 calc R . . C4 C 0.72062(12) 0.61663(10) -0.11387(10) 0.0218(2) Uani 1 1 d . . . H4 H 0.7520 0.6099 -0.1936 0.026 Uiso 1 1 calc R . . C4A C 0.80362(11) 0.62733(9) -0.04799(10) 0.0182(2) Uani 1 1 d . . . C5 C 1.13884(12) 0.64224(10) -0.08243(12) 0.0248(3) Uani 1 1 d . . . H5 H 1.1728 0.6331 -0.1619 0.030 Uiso 1 1 calc R . . C6 C 1.21388(12) 0.65672(11) -0.01697(13) 0.0291(3) Uani 1 1 d . . . H6 H 1.2995 0.6581 -0.0513 0.035 Uiso 1 1 calc R . . C7 C 1.16554(12) 0.66964(10) 0.10150(13) 0.0286(3) Uani 1 1 d . . . H7 H 1.2192 0.6795 0.1459 0.034 Uiso 1 1 calc R . . C8 C 1.04334(12) 0.66818(10) 0.15270(12) 0.0240(3) Uani 1 1 d . . . H8 H 1.0125 0.6767 0.2324 0.029 Uiso 1 1 calc R . . C8A C 0.96085(11) 0.65390(9) 0.08771(10) 0.0186(2) Uani 1 1 d . . . C9 C 0.83416(11) 0.65179(9) 0.13727(10) 0.0177(2) Uani 1 1 d . . . C9A C 0.75412(11) 0.63861(9) 0.07229(10) 0.0176(2) Uani 1 1 d . . . C10 C 0.93006(11) 0.62722(9) -0.09725(10) 0.0198(2) Uani 1 1 d . . . H10 H 0.9629 0.6177 -0.1768 0.024 Uiso 1 1 calc R . . C10A C 1.00960(11) 0.64072(9) -0.03244(10) 0.0192(2) Uani 1 1 d . . . C11 C 0.78434(11) 0.66649(10) 0.26319(10) 0.0193(2) Uani 1 1 d . . . O1 O 0.73435(9) 0.75613(7) 0.31382(8) 0.0278(2) Uani 1 1 d . . . O2 O 0.80626(8) 0.56751(7) 0.31064(7) 0.02064(18) Uani 1 1 d . . . C12 C 0.77259(11) 0.56920(10) 0.43413(10) 0.0190(2) Uani 1 1 d . . . H12 H 0.7987 0.6318 0.4637 0.023 Uiso 1 1 calc R . . C13 C 0.63079(12) 0.58408(11) 0.48309(11) 0.0262(3) Uani 1 1 d . . . H13A H 0.6037 0.5258 0.4490 0.031 Uiso 1 1 calc R . . H13B H 0.5837 0.6588 0.4654 0.031 Uiso 1 1 calc R . . C14 C 0.59983(12) 0.57424(11) 0.61086(11) 0.0265(3) Uani 1 1 d . . . H14A H 0.6212 0.6360 0.6452 0.032 Uiso 1 1 calc R . . H14B H 0.5075 0.5817 0.6420 0.032 Uiso 1 1 calc R . . C15 C 0.67448(13) 0.46165(11) 0.64057(11) 0.0261(3) Uani 1 1 d . . . H15A H 0.6470 0.4001 0.6124 0.031 Uiso 1 1 calc R . . H15B H 0.6563 0.4586 0.7234 0.031 Uiso 1 1 calc R . . C16 C 0.81702(12) 0.44464(11) 0.58906(11) 0.0246(3) Uani 1 1 d . . . H16A H 0.8629 0.3687 0.6049 0.030 Uiso 1 1 calc R . . H16B H 0.8463 0.5006 0.6242 0.030 Uiso 1 1 calc R . . C17 C 0.84878(12) 0.45717(10) 0.46175(10) 0.0215(2) Uani 1 1 d . . . H17A H 0.9408 0.4516 0.4316 0.026 Uiso 1 1 calc R . . H17B H 0.8295 0.3954 0.4254 0.026 Uiso 1 1 calc R . . C21 C 1.05371(12) 0.16719(10) 0.31058(11) 0.0222(2) Uani 1 1 d . . . H21 H 1.0161 0.1777 0.2497 0.027 Uiso 1 1 calc R . . C22 C 1.17927(12) 0.16357(10) 0.29127(12) 0.0273(3) Uani 1 1 d . . . H22 H 1.2283 0.1717 0.2173 0.033 Uiso 1 1 calc R . . C23 C 1.23720(12) 0.14775(11) 0.38104(13) 0.0299(3) Uani 1 1 d . . . H23 H 1.3248 0.1454 0.3667 0.036 Uiso 1 1 calc R . . C24 C 1.16865(12) 0.13598(10) 0.48726(12) 0.0268(3) Uani 1 1 d . . . H24 H 1.2090 0.1251 0.5463 0.032 Uiso 1 1 calc R . . C24A C 1.03660(11) 0.13966(9) 0.51158(11) 0.0206(2) Uani 1 1 d . . . C25 C 0.75976(14) 0.12245(10) 0.75364(11) 0.0280(3) Uani 1 1 d . . . H25 H 0.7986 0.1107 0.8137 0.034 Uiso 1 1 calc R . . C26 C 0.63420(15) 0.12859(11) 0.77492(12) 0.0326(3) Uani 1 1 d . . . H26 H 0.5858 0.1222 0.8496 0.039 Uiso 1 1 calc R . . C27 C 0.57433(13) 0.14454(11) 0.68626(12) 0.0296(3) Uani 1 1 d . . . H27 H 0.4863 0.1481 0.7020 0.035 Uiso 1 1 calc R . . C28 C 0.64215(12) 0.15480(10) 0.57906(11) 0.0238(3) Uani 1 1 d . . . H28 H 0.6009 0.1653 0.5206 0.029 Uiso 1 1 calc R . . C28A C 0.77451(11) 0.14996(9) 0.55318(10) 0.0196(2) Uani 1 1 d . . . C29 C 0.84814(11) 0.15974(9) 0.44416(10) 0.0176(2) Uani 1 1 d . . . C29A C 0.97792(11) 0.15545(9) 0.42089(10) 0.0185(2) Uani 1 1 d . . . C30 C 0.96386(12) 0.12799(10) 0.61965(11) 0.0231(3) Uani 1 1 d . . . H30 H 1.0033 0.1161 0.6793 0.028 Uiso 1 1 calc R . . C30A C 0.83492(12) 0.13325(9) 0.64282(10) 0.0217(2) Uani 1 1 d . . . C31 C 0.78714(11) 0.17402(9) 0.34925(10) 0.0187(2) Uani 1 1 d . . . O21 O 0.72352(9) 0.26147(7) 0.32683(8) 0.0253(2) Uani 1 1 d . . . O22 O 0.81430(8) 0.07530(7) 0.29238(7) 0.02036(18) Uani 1 1 d . . . C32 C 0.76780(11) 0.07456(10) 0.19293(10) 0.0201(2) Uani 1 1 d . . . H32 H 0.7815 0.1408 0.1477 0.024 Uiso 1 1 calc R . . C33 C 0.84788(12) -0.03331(10) 0.12576(10) 0.0225(2) Uani 1 1 d . . . H33A H 0.8408 -0.0983 0.1735 0.027 Uiso 1 1 calc R . . H33B H 0.9383 -0.0316 0.1024 0.027 Uiso 1 1 calc R . . C34 C 0.80380(14) -0.04740(12) 0.02171(11) 0.0294(3) Uani 1 1 d . . . H34A H 0.8198 0.0131 -0.0299 0.035 Uiso 1 1 calc R . . H34B H 0.8535 -0.1205 -0.0185 0.035 Uiso 1 1 calc R . . C35 C 0.66268(14) -0.04284(12) 0.05378(12) 0.0317(3) Uani 1 1 d . . . H35A H 0.6482 -0.1086 0.0979 0.038 Uiso 1 1 calc R . . H35B H 0.6354 -0.0469 -0.0154 0.038 Uiso 1 1 calc R . . C36 C 0.58298(14) 0.06517(12) 0.12302(14) 0.0365(3) Uani 1 1 d . . . H36A H 0.4924 0.0637 0.1465 0.044 Uiso 1 1 calc R . . H36B H 0.5900 0.1306 0.0760 0.044 Uiso 1 1 calc R . . C37 C 0.62744(12) 0.07817(11) 0.22734(12) 0.0279(3) Uani 1 1 d . . . H37A H 0.5777 0.1507 0.2687 0.033 Uiso 1 1 calc R . . H37B H 0.6129 0.0167 0.2781 0.033 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 C1 0.0206(6) 0.0211(5) 0.0214(6) -0.0018(4) -0.0034(5) -0.0053(4) C2 0.0172(5) 0.0266(6) 0.0311(7) -0.0039(5) -0.0051(5) -0.0054(5) C3 0.0242(6) 0.0262(6) 0.0289(7) -0.0035(5) -0.0137(5) -0.0044(5) C4 0.0254(6) 0.0219(5) 0.0191(6) -0.0013(4) -0.0091(5) -0.0044(4) C4A 0.0211(5) 0.0156(5) 0.0182(5) 0.0011(4) -0.0064(4) -0.0043(4) C5 0.0207(6) 0.0196(5) 0.0317(7) 0.0047(5) -0.0029(5) -0.0059(4) C6 0.0196(6) 0.0211(6) 0.0471(8) 0.0052(5) -0.0081(6) -0.0075(5) C7 0.0248(6) 0.0216(6) 0.0458(8) 0.0010(5) -0.0187(6) -0.0076(5) C8 0.0262(6) 0.0192(5) 0.0301(7) 0.0004(5) -0.0143(5) -0.0053(5) C8A 0.0206(5) 0.0141(5) 0.0225(6) 0.0019(4) -0.0084(5) -0.0047(4) C9 0.0212(5) 0.0152(5) 0.0176(5) 0.0016(4) -0.0068(4) -0.0049(4) C9A 0.0196(5) 0.0155(5) 0.0181(5) 0.0004(4) -0.0061(4) -0.0039(4) C10 0.0227(6) 0.0176(5) 0.0183(5) 0.0024(4) -0.0045(4) -0.0049(4) C10A 0.0203(5) 0.0144(5) 0.0229(6) 0.0037(4) -0.0055(5) -0.0050(4) C11 0.0217(5) 0.0200(5) 0.0187(5) 0.0016(4) -0.0086(4) -0.0065(4) O1 0.0414(5) 0.0192(4) 0.0214(4) -0.0007(3) -0.0104(4) -0.0035(4) O2 0.0281(4) 0.0181(4) 0.0152(4) 0.0013(3) -0.0055(3) -0.0055(3) C12 0.0238(6) 0.0193(5) 0.0145(5) 0.0009(4) -0.0058(4) -0.0059(4) C13 0.0218(6) 0.0321(7) 0.0233(6) 0.0019(5) -0.0068(5) -0.0036(5) C14 0.0223(6) 0.0313(6) 0.0223(6) -0.0008(5) -0.0017(5) -0.0050(5) C15 0.0324(7) 0.0250(6) 0.0202(6) 0.0024(5) -0.0031(5) -0.0107(5) C16 0.0280(6) 0.0236(6) 0.0209(6) 0.0039(5) -0.0076(5) -0.0036(5) C17 0.0233(6) 0.0206(5) 0.0188(6) 0.0015(4) -0.0047(5) -0.0033(4) C21 0.0237(6) 0.0187(5) 0.0242(6) 0.0012(4) -0.0066(5) -0.0056(4) C22 0.0236(6) 0.0216(6) 0.0344(7) 0.0011(5) -0.0026(5) -0.0073(5) C23 0.0211(6) 0.0219(6) 0.0489(9) -0.0006(6) -0.0119(6) -0.0068(5) C24 0.0260(6) 0.0186(5) 0.0414(8) -0.0014(5) -0.0199(6) -0.0043(5) C24A 0.0238(6) 0.0131(5) 0.0273(6) -0.0011(4) -0.0129(5) -0.0027(4) C25 0.0429(8) 0.0190(6) 0.0195(6) 0.0009(5) -0.0085(5) -0.0033(5) C26 0.0435(8) 0.0221(6) 0.0233(7) 0.0008(5) 0.0024(6) -0.0052(5) C27 0.0269(6) 0.0204(6) 0.0336(7) -0.0003(5) 0.0021(5) -0.0035(5) C28 0.0229(6) 0.0188(5) 0.0276(6) 0.0006(5) -0.0060(5) -0.0029(4) C28A 0.0230(6) 0.0137(5) 0.0211(6) 0.0002(4) -0.0067(5) -0.0024(4) C29 0.0210(5) 0.0132(5) 0.0199(5) 0.0002(4) -0.0090(4) -0.0031(4) C29A 0.0213(5) 0.0132(5) 0.0224(6) -0.0004(4) -0.0088(5) -0.0037(4) C30 0.0323(6) 0.0161(5) 0.0240(6) -0.0006(4) -0.0167(5) -0.0021(5) C30A 0.0307(6) 0.0138(5) 0.0197(6) 0.0001(4) -0.0087(5) -0.0025(4) C31 0.0191(5) 0.0190(5) 0.0194(5) 0.0017(4) -0.0062(4) -0.0066(4) O21 0.0298(5) 0.0196(4) 0.0289(5) 0.0011(3) -0.0157(4) -0.0024(3) O22 0.0252(4) 0.0182(4) 0.0210(4) 0.0008(3) -0.0129(3) -0.0046(3) C32 0.0249(6) 0.0196(5) 0.0208(6) 0.0037(4) -0.0136(5) -0.0071(4) C33 0.0241(6) 0.0242(6) 0.0197(6) 0.0008(4) -0.0081(5) -0.0052(5) C34 0.0399(8) 0.0299(7) 0.0205(6) 0.0000(5) -0.0122(6) -0.0083(6) C35 0.0399(8) 0.0292(7) 0.0331(7) -0.0038(5) -0.0234(6) -0.0066(6) C36 0.0338(7) 0.0322(7) 0.0502(9) -0.0087(6) -0.0288(7) -0.0012(6) C37 0.0226(6) 0.0286(6) 0.0340(7) -0.0074(5) -0.0123(5) -0.0039(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 C2 1.3595(17) . ? C1 C9A 1.4310(16) . ? C1 H1 0.9500 . ? C2 C3 1.4210(19) . ? C2 H2 0.9500 . ? C3 C4 1.3571(18) . ? C3 H3 0.9500 . ? C4 C4A 1.4281(16) . ? C4 H4 0.9500 . ? C4A C10 1.3930(16) . ? C4A C9A 1.4349(16) . ? C5 C6 1.3633(19) . ? C5 C10A 1.4284(16) . ? C5 H5 0.9500 . ? C6 C7 1.414(2) . ? C6 H6 0.9500 . ? C7 C8 1.3591(18) . ? C7 H7 0.9500 . ? C8 C8A 1.4278(16) . ? C8 H8 0.9500 . ? C8A C9 1.4033(16) . ? C8A C10A 1.4333(17) . ? C9 C9A 1.4006(16) . ? C9 C11 1.5016(16) . ? C10 C10A 1.3955(17) . ? C10 H10 0.9500 . ? C11 O1 1.2028(14) . ? C11 O2 1.3352(14) . ? O2 C12 1.4680(14) . ? C12 C17 1.5132(16) . ? C12 C13 1.5156(17) . ? C12 H12 1.0000 . ? C13 C14 1.5305(18) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5212(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5236(18) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5290(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C21 C22 1.3627(17) . ? C21 C29A 1.4264(17) . ? C21 H21 0.9500 . ? C22 C23 1.419(2) . ? C22 H22 0.9500 . ? C23 C24 1.357(2) . ? C23 H23 0.9500 . ? C24 C24A 1.4291(17) . ? C24 H24 0.9500 . ? C24A C30 1.3918(18) . ? C24A C29A 1.4348(16) . ? C25 C26 1.354(2) . ? C25 C30A 1.4262(18) . ? C25 H25 0.9500 . ? C26 C27 1.421(2) . ? C26 H26 0.9500 . ? C27 C28 1.3602(19) . ? C27 H27 0.9500 . ? C28 C28A 1.4280(17) . ? C28 H28 0.9500 . ? C28A C29 1.3995(17) . ? C28A C30A 1.4356(17) . ? C29 C29A 1.4031(16) . ? C29 C31 1.4987(16) . ? C30 C30A 1.3913(18) . ? C30 H30 0.9500 . ? C31 O21 1.2045(14) . ? C31 O22 1.3390(14) . ? O22 C32 1.4618(13) . ? C32 C33 1.5152(16) . ? C32 C37 1.5160(17) . ? C32 H32 1.0000 . ? C33 C34 1.5263(17) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.522(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.5260(19) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.5291(19) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.83(11) . . ? C2 C1 H1 119.6 . . ? C9A C1 H1 119.6 . . ? C1 C2 C3 120.81(12) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.06(11) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 121.37(11) . . ? C3 C4 H4 119.3 . . ? C4A C4 H4 119.3 . . ? C10 C4A C4 121.88(11) . . ? C10 C4A C9A 119.63(10) . . ? C4 C4A C9A 118.49(11) . . ? C6 C5 C10A 120.52(13) . . ? C6 C5 H5 119.7 . . ? C10A C5 H5 119.7 . . ? C5 C6 C7 120.64(12) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.84(12) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 120.58(12) . . ? C7 C8 H8 119.7 . . ? C8A C8 H8 119.7 . . ? C9 C8A C8 122.37(11) . . ? C9 C8A C10A 118.93(10) . . ? C8 C8A C10A 118.71(11) . . ? C9A C9 C8A 121.68(11) . . ? C9A C9 C11 120.06(10) . . ? C8A C9 C11 118.25(10) . . ? C9 C9A C1 122.81(11) . . ? C9 C9A C4A 118.77(10) . . ? C1 C9A C4A 118.41(10) . . ? C4A C10 C10A 121.53(11) . . ? C4A C10 H10 119.2 . . ? C10A C10 H10 119.2 . . ? C10 C10A C5 121.86(11) . . ? C10 C10A C8A 119.44(11) . . ? C5 C10A C8A 118.71(11) . . ? O1 C11 O2 125.02(11) . . ? O1 C11 C9 124.04(11) . . ? O2 C11 C9 110.91(9) . . ? C11 O2 C12 117.23(9) . . ? O2 C12 C17 105.09(9) . . ? O2 C12 C13 110.87(9) . . ? C17 C12 C13 111.57(10) . . ? O2 C12 H12 109.7 . . ? C17 C12 H12 109.7 . . ? C13 C12 H12 109.7 . . ? C12 C13 C14 109.91(10) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 110.82(10) . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 110.99(10) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 111.37(10) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C12 C17 C16 110.72(10) . . ? C12 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C22 C21 C29A 120.94(12) . . ? C22 C21 H21 119.5 . . ? C29A C21 H21 119.5 . . ? C21 C22 C23 120.37(13) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.63(12) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C24A 120.96(12) . . ? C23 C24 H24 119.5 . . ? C24A C24 H24 119.5 . . ? C30 C24A C24 122.25(11) . . ? C30 C24A C29A 119.26(11) . . ? C24 C24A C29A 118.49(12) . . ? C26 C25 C30A 121.29(13) . . ? C26 C25 H25 119.4 . . ? C30A C25 H25 119.4 . . ? C25 C26 C27 120.41(13) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 120.46(13) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C28A 120.91(12) . . ? C27 C28 H28 119.5 . . ? C28A C28 H28 119.5 . . ? C29 C28A C28 122.90(11) . . ? C29 C28A C30A 118.58(11) . . ? C28 C28A C30A 118.52(11) . . ? C28A C29 C29A 121.88(11) . . ? C28A C29 C31 119.14(10) . . ? C29A C29 C31 118.98(10) . . ? C29 C29A C21 122.54(11) . . ? C29 C29A C24A 118.84(11) . . ? C21 C29A C24A 118.61(11) . . ? C30A C30 C24A 121.85(11) . . ? C30A C30 H30 119.1 . . ? C24A C30 H30 119.1 . . ? C30 C30A C25 122.02(12) . . ? C30 C30A C28A 119.58(11) . . ? C25 C30A C28A 118.40(12) . . ? O21 C31 O22 124.83(11) . . ? O21 C31 C29 125.12(10) . . ? O22 C31 C29 110.05(9) . . ? C31 O22 C32 117.54(9) . . ? O22 C32 C33 105.30(9) . . ? O22 C32 C37 110.43(10) . . ? C33 C32 C37 111.72(10) . . ? O22 C32 H32 109.8 . . ? C33 C32 H32 109.8 . . ? C37 C32 H32 109.8 . . ? C32 C33 C34 110.55(10) . . ? C32 C33 H33A 109.5 . . ? C34 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C35 C34 C33 111.12(11) . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34B 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.22(11) . . ? C34 C35 H35A 109.4 . . ? C36 C35 H35A 109.4 . . ? C34 C35 H35B 109.4 . . ? C36 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C37 111.05(11) . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36B 109.4 . . ? C37 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C32 C37 C36 110.02(12) . . ? C32 C37 H37A 109.7 . . ? C36 C37 H37A 109.7 . . ? C32 C37 H37B 109.7 . . ? C36 C37 H37B 109.7 . . ? H37A C37 H37B 108.2 . . ? 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 C9A C1 C2 C3 0.52(18) . . . . ? C1 C2 C3 C4 0.59(19) . . . . ? C2 C3 C4 C4A -0.49(18) . . . . ? C3 C4 C4A C10 179.41(11) . . . . ? C3 C4 C4A C9A -0.68(17) . . . . ? C10A C5 C6 C7 0.48(18) . . . . ? C5 C6 C7 C8 -0.15(19) . . . . ? C6 C7 C8 C8A -0.21(18) . . . . ? C7 C8 C8A C9 179.93(11) . . . . ? C7 C8 C8A C10A 0.24(17) . . . . ? C8 C8A C9 C9A 179.48(11) . . . . ? C10A C8A C9 C9A -0.83(16) . . . . ? C8 C8A C9 C11 0.71(16) . . . . ? C10A C8A C9 C11 -179.60(10) . . . . ? C8A C9 C9A C1 179.58(10) . . . . ? C11 C9 C9A C1 -1.67(17) . . . . ? C8A C9 C9A C4A -0.16(16) . . . . ? C11 C9 C9A C4A 178.59(10) . . . . ? C2 C1 C9A C9 178.59(11) . . . . ? C2 C1 C9A C4A -1.67(17) . . . . ? C10 C4A C9A C9 1.40(16) . . . . ? C4 C4A C9A C9 -178.52(10) . . . . ? C10 C4A C9A C1 -178.35(10) . . . . ? C4 C4A C9A C1 1.73(16) . . . . ? C4 C4A C10 C10A 178.27(11) . . . . ? C9A C4A C10 C10A -1.65(17) . . . . ? C4A C10 C10A C5 -179.12(11) . . . . ? C4A C10 C10A C8A 0.64(17) . . . . ? C6 C5 C10A C10 179.33(11) . . . . ? C6 C5 C10A C8A -0.44(17) . . . . ? C9 C8A C10A C10 0.60(16) . . . . ? C8 C8A C10A C10 -179.69(10) . . . . ? C9 C8A C10A C5 -179.63(10) . . . . ? C8 C8A C10A C5 0.08(16) . . . . ? C9A C9 C11 O1 -89.10(15) . . . . ? C8A C9 C11 O1 89.69(15) . . . . ? C9A C9 C11 O2 92.61(12) . . . . ? C8A C9 C11 O2 -88.60(12) . . . . ? O1 C11 O2 C12 -3.32(17) . . . . ? C9 C11 O2 C12 174.95(9) . . . . ? C11 O2 C12 C17 -159.97(10) . . . . ? C11 O2 C12 C13 79.35(12) . . . . ? O2 C12 C13 C14 174.58(10) . . . . ? C17 C12 C13 C14 57.82(13) . . . . ? C12 C13 C14 C15 -57.40(14) . . . . ? C13 C14 C15 C16 56.33(14) . . . . ? C14 C15 C16 C17 -54.96(14) . . . . ? O2 C12 C17 C16 -176.82(9) . . . . ? C13 C12 C17 C16 -56.60(13) . . . . ? C15 C16 C17 C12 54.78(14) . . . . ? C29A C21 C22 C23 0.11(18) . . . . ? C21 C22 C23 C24 0.02(19) . . . . ? C22 C23 C24 C24A -0.27(19) . . . . ? C23 C24 C24A C30 -179.91(11) . . . . ? C23 C24 C24A C29A 0.36(17) . . . . ? C30A C25 C26 C27 0.86(19) . . . . ? C25 C26 C27 C28 -0.56(19) . . . . ? C26 C27 C28 C28A -0.08(18) . . . . ? C27 C28 C28A C29 179.79(11) . . . . ? C27 C28 C28A C30A 0.40(17) . . . . ? C28 C28A C29 C29A 179.58(10) . . . . ? C30A C28A C29 C29A -1.03(16) . . . . ? C28 C28A C29 C31 -1.06(16) . . . . ? C30A C28A C29 C31 178.32(10) . . . . ? C28A C29 C29A C21 -178.91(10) . . . . ? C31 C29 C29A C21 1.73(16) . . . . ? C28A C29 C29A C24A 0.51(16) . . . . ? C31 C29 C29A C24A -178.84(10) . . . . ? C22 C21 C29A C29 179.42(11) . . . . ? C22 C21 C29A C24A -0.01(17) . . . . ? C30 C24A C29A C29 0.60(16) . . . . ? C24 C24A C29A C29 -179.67(10) . . . . ? C30 C24A C29A C21 -179.96(10) . . . . ? C24 C24A C29A C21 -0.22(15) . . . . ? C24 C24A C30 C30A 179.09(11) . . . . ? C29A C24A C30 C30A -1.19(17) . . . . ? C24A C30 C30A C25 -179.37(11) . . . . ? C24A C30 C30A C28A 0.66(17) . . . . ? C26 C25 C30A C30 179.51(12) . . . . ? C26 C25 C30A C28A -0.52(17) . . . . ? C29 C28A C30A C30 0.45(16) . . . . ? C28 C28A C30A C30 179.86(10) . . . . ? C29 C28A C30A C25 -179.52(10) . . . . ? C28 C28A C30A C25 -0.11(16) . . . . ? C28A C29 C31 O21 80.78(15) . . . . ? C29A C29 C31 O21 -99.84(14) . . . . ? C28A C29 C31 O22 -99.59(12) . . . . ? C29A C29 C31 O22 79.79(13) . . . . ? O21 C31 O22 C32 2.72(17) . . . . ? C29 C31 O22 C32 -176.91(9) . . . . ? C31 O22 C32 C33 161.05(10) . . . . ? C31 O22 C32 C37 -78.19(12) . . . . ? O22 C32 C33 C34 177.04(10) . . . . ? C37 C32 C33 C34 57.13(14) . . . . ? C32 C33 C34 C35 -55.53(14) . . . . ? C33 C34 C35 C36 55.19(15) . . . . ? C34 C35 C36 C37 -55.68(17) . . . . ? O22 C32 C37 C36 -174.20(10) . . . . ? C33 C32 C37 C36 -57.36(14) . . . . ? C35 C36 C37 C32 56.23(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.394 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.044 # Attachment 'cb21_0m_MAE.cif' data_cb21_0m _database_code_depnum_ccdc_archive 'CCDC 808569' #TrackingRef 'cb21_0m_MAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 O2' _chemical_formula_weight 236.26 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2274(4) _cell_length_b 7.6159(3) _cell_length_c 14.2498(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.9815(5) _cell_angle_gamma 90.00 _cell_volume 1177.04(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7262 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 31.37 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9536 _exptl_absorpt_correction_T_max 0.9636 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 12258 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3170 _reflns_number_gt 2837 _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^)+(0.0738P)^2^+0.2617P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3170 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1207 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.28323(8) -0.06123(12) 0.80814(6) 0.01861(19) Uani 1 1 d . . . H1 H 0.2119 -0.1324 0.8009 0.022 Uiso 1 1 calc R . . C2 C 0.34573(9) -0.06204(13) 0.73769(7) 0.0213(2) Uani 1 1 d . . . H2 H 0.3169 -0.1330 0.6816 0.026 Uiso 1 1 calc R . . C3 C 0.45331(9) 0.04196(13) 0.74720(7) 0.0203(2) Uani 1 1 d . . . H3 H 0.4961 0.0393 0.6978 0.024 Uiso 1 1 calc R . . C4 C 0.49532(8) 0.14544(12) 0.82682(6) 0.01720(18) Uani 1 1 d . . . H4 H 0.5674 0.2143 0.8325 0.021 Uiso 1 1 calc R . . C4A C 0.43227(8) 0.15171(11) 0.90193(6) 0.01448(18) Uani 1 1 d . . . C5 C 0.45575(8) 0.37424(12) 1.14072(6) 0.01790(19) Uani 1 1 d . . . H5 H 0.5292 0.4407 1.1479 0.021 Uiso 1 1 calc R . . C6 C 0.39264(9) 0.38409(13) 1.21034(7) 0.0209(2) Uani 1 1 d . . . H6 H 0.4220 0.4575 1.2654 0.025 Uiso 1 1 calc R . . C7 C 0.28289(9) 0.28474(13) 1.20076(7) 0.0210(2) Uani 1 1 d . . . H7 H 0.2385 0.2944 1.2490 0.025 Uiso 1 1 calc R . . C8 C 0.24043(8) 0.17566(12) 1.12333(7) 0.01834(19) Uani 1 1 d . . . H8 H 0.1676 0.1089 1.1187 0.022 Uiso 1 1 calc R . . C8A C 0.30479(8) 0.16115(11) 1.04910(6) 0.01447(18) Uani 1 1 d . . . C9 C 0.26477(8) 0.04960(11) 0.96855(6) 0.01449(18) Uani 1 1 d . . . C9A C 0.32419(8) 0.04590(11) 0.89280(6) 0.01444(18) Uani 1 1 d . . . C10 C 0.47538(8) 0.25612(11) 0.98423(6) 0.01519(18) Uani 1 1 d . . . H10 H 0.5488 0.3223 0.9908 0.018 Uiso 1 1 calc R . . C10A C 0.41310(8) 0.26545(11) 1.05714(6) 0.01450(18) Uani 1 1 d . . . C11 C 0.16062(8) -0.07405(12) 0.96566(6) 0.01757(19) Uani 1 1 d . . . O1 O 0.06023(7) -0.06749(12) 0.91059(6) 0.0313(2) Uani 1 1 d . . . O2 O 0.19496(6) -0.19930(10) 1.03323(5) 0.02535(18) Uani 1 1 d . . . C12 C 0.10113(11) -0.32700(15) 1.03748(8) 0.0311(3) Uani 1 1 d . . . H12A H 0.0340 -0.2690 1.0578 0.047 Uiso 1 1 calc R . . H12B H 0.1370 -0.4189 1.0844 0.047 Uiso 1 1 calc R . . H12C H 0.0688 -0.3796 0.9732 0.047 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 C1 0.0193(4) 0.0173(4) 0.0180(4) -0.0009(3) 0.0025(3) -0.0023(3) C2 0.0252(5) 0.0209(4) 0.0169(4) -0.0033(3) 0.0039(3) -0.0001(3) C3 0.0238(4) 0.0209(4) 0.0176(4) 0.0013(3) 0.0081(3) 0.0026(3) C4 0.0175(4) 0.0168(4) 0.0186(4) 0.0028(3) 0.0070(3) 0.0007(3) C4A 0.0149(4) 0.0131(4) 0.0155(4) 0.0026(3) 0.0040(3) 0.0009(3) C5 0.0196(4) 0.0156(4) 0.0176(4) -0.0005(3) 0.0032(3) -0.0023(3) C6 0.0246(4) 0.0202(4) 0.0175(4) -0.0029(3) 0.0046(3) 0.0006(3) C7 0.0214(4) 0.0250(5) 0.0182(4) 0.0003(3) 0.0079(3) 0.0025(3) C8 0.0157(4) 0.0217(4) 0.0185(4) 0.0021(3) 0.0060(3) 0.0000(3) C8A 0.0135(4) 0.0147(4) 0.0149(4) 0.0023(3) 0.0031(3) 0.0003(3) C9 0.0125(4) 0.0147(4) 0.0154(4) 0.0026(3) 0.0021(3) -0.0009(3) C9A 0.0146(4) 0.0131(4) 0.0147(4) 0.0021(3) 0.0022(3) 0.0005(3) C10 0.0146(4) 0.0137(4) 0.0173(4) 0.0017(3) 0.0042(3) -0.0016(3) C10A 0.0150(4) 0.0126(4) 0.0155(4) 0.0013(3) 0.0032(3) 0.0001(3) C11 0.0165(4) 0.0202(4) 0.0159(4) 0.0010(3) 0.0039(3) -0.0038(3) O1 0.0170(3) 0.0450(5) 0.0275(4) 0.0120(3) -0.0022(3) -0.0092(3) O2 0.0220(3) 0.0227(4) 0.0274(4) 0.0090(3) -0.0008(3) -0.0093(3) C12 0.0330(5) 0.0294(5) 0.0291(5) 0.0055(4) 0.0046(4) -0.0183(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 C2 1.3654(12) . ? C1 C9A 1.4303(12) . ? C1 H1 0.9500 . ? C2 C3 1.4213(13) . ? C2 H2 0.9500 . ? C3 C4 1.3617(13) . ? C3 H3 0.9500 . ? C4 C4A 1.4285(11) . ? C4 H4 0.9500 . ? C4A C10 1.3958(12) . ? C4A C9A 1.4343(12) . ? C5 C6 1.3621(12) . ? C5 C10A 1.4280(12) . ? C5 H5 0.9500 . ? C6 C7 1.4222(13) . ? C6 H6 0.9500 . ? C7 C8 1.3649(13) . ? C7 H7 0.9500 . ? C8 C8A 1.4312(11) . ? C8 H8 0.9500 . ? C8A C9 1.4052(12) . ? C8A C10A 1.4321(12) . ? C9 C9A 1.4082(11) . ? C9 C11 1.4937(11) . ? C10 C10A 1.3961(11) . ? C10 H10 0.9500 . ? C11 O1 1.1965(12) . ? C11 O2 1.3392(11) . ? O2 C12 1.4465(11) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.56(8) . . ? C2 C1 H1 119.7 . . ? C9A C1 H1 119.7 . . ? C1 C2 C3 120.86(8) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.32(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C4A 120.77(8) . . ? C3 C4 H4 119.6 . . ? C4A C4 H4 119.6 . . ? C10 C4A C4 121.14(8) . . ? C10 C4A C9A 119.85(8) . . ? C4 C4A C9A 119.00(8) . . ? C6 C5 C10A 120.93(8) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 120.12(8) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.95(8) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C8A 120.46(8) . . ? C7 C8 H8 119.8 . . ? C8A C8 H8 119.8 . . ? C9 C8A C8 122.31(8) . . ? C9 C8A C10A 119.10(7) . . ? C8 C8A C10A 118.59(8) . . ? C8A C9 C9A 121.56(7) . . ? C8A C9 C11 119.10(7) . . ? C9A C9 C11 119.27(7) . . ? C9 C9A C1 123.04(8) . . ? C9 C9A C4A 118.46(7) . . ? C1 C9A C4A 118.49(8) . . ? C4A C10 C10A 121.51(8) . . ? C4A C10 H10 119.2 . . ? C10A C10 H10 119.2 . . ? C10 C10A C5 121.72(8) . . ? C10 C10A C8A 119.37(8) . . ? C5 C10A C8A 118.90(8) . . ? O1 C11 O2 123.27(8) . . ? O1 C11 C9 126.14(8) . . ? O2 C11 C9 110.58(7) . . ? C11 O2 C12 115.57(8) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C9A C1 C2 C3 0.60(14) . . . . ? C1 C2 C3 C4 -0.48(14) . . . . ? C2 C3 C4 C4A -0.11(14) . . . . ? C3 C4 C4A C10 179.37(8) . . . . ? C3 C4 C4A C9A 0.55(13) . . . . ? C10A C5 C6 C7 0.27(14) . . . . ? C5 C6 C7 C8 1.39(14) . . . . ? C6 C7 C8 C8A -0.99(14) . . . . ? C7 C8 C8A C9 179.55(8) . . . . ? C7 C8 C8A C10A -1.02(13) . . . . ? C8 C8A C9 C9A 175.53(8) . . . . ? C10A C8A C9 C9A -3.90(12) . . . . ? C8 C8A C9 C11 -7.49(13) . . . . ? C10A C8A C9 C11 173.09(7) . . . . ? C8A C9 C9A C1 -177.66(8) . . . . ? C11 C9 C9A C1 5.35(12) . . . . ? C8A C9 C9A C4A 3.67(12) . . . . ? C11 C9 C9A C4A -173.31(7) . . . . ? C2 C1 C9A C9 -178.81(8) . . . . ? C2 C1 C9A C4A -0.15(13) . . . . ? C10 C4A C9A C9 -0.53(12) . . . . ? C4 C4A C9A C9 178.31(7) . . . . ? C10 C4A C9A C1 -179.26(8) . . . . ? C4 C4A C9A C1 -0.42(12) . . . . ? C4 C4A C10 C10A 178.83(8) . . . . ? C9A C4A C10 C10A -2.35(13) . . . . ? C4A C10 C10A C5 -178.98(8) . . . . ? C4A C10 C10A C8A 2.13(13) . . . . ? C6 C5 C10A C10 178.84(8) . . . . ? C6 C5 C10A C8A -2.26(13) . . . . ? C9 C8A C10A C10 0.97(12) . . . . ? C8 C8A C10A C10 -178.48(8) . . . . ? C9 C8A C10A C5 -177.95(8) . . . . ? C8 C8A C10A C5 2.60(12) . . . . ? C8A C9 C11 O1 112.66(11) . . . . ? C9A C9 C11 O1 -70.28(13) . . . . ? C8A C9 C11 O2 -68.53(10) . . . . ? C9A C9 C11 O2 108.53(9) . . . . ? O1 C11 O2 C12 -1.30(14) . . . . ? C9 C11 O2 C12 179.85(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.367 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.054 # Attachment 'cb22_0m_EAE.cif' data_cb22_0m _database_code_depnum_ccdc_archive 'CCDC 808570' #TrackingRef 'cb22_0m_EAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 O2' _chemical_formula_weight 250.28 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 8.5056(7) _cell_length_b 10.1688(8) _cell_length_c 14.4684(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1251.40(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7559 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 31.02 _exptl_crystal_description 'needle frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9502 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 17886 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 30.02 _reflns_number_total 3654 _reflns_number_gt 3457 _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^)+(0.0538P)^2^+0.1680P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.9(8) _refine_ls_number_reflns 3654 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.062 _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 0.37328(13) -0.03776(11) 0.30948(7) 0.0168(2) Uani 1 1 d . . . H1 H 0.4092 -0.1230 0.2929 0.020 Uiso 1 1 calc R . . C2 C 0.42319(13) 0.01809(11) 0.39028(8) 0.0184(2) Uani 1 1 d . . . H2 H 0.4945 -0.0283 0.4289 0.022 Uiso 1 1 calc R . . C3 C 0.36939(13) 0.14517(12) 0.41722(8) 0.0191(2) Uani 1 1 d . . . H3 H 0.4043 0.1826 0.4738 0.023 Uiso 1 1 calc R . . C4 C 0.26807(13) 0.21310(11) 0.36220(8) 0.0173(2) Uani 1 1 d . . . H4 H 0.2318 0.2972 0.3812 0.021 Uiso 1 1 calc R . . C4A C 0.21553(12) 0.15977(10) 0.27633(7) 0.01480(19) Uani 1 1 d . . . C5 C -0.03790(13) 0.25017(11) 0.07424(8) 0.0190(2) Uani 1 1 d . . . H5 H -0.0719 0.3357 0.0916 0.023 Uiso 1 1 calc R . . C6 C -0.08853(14) 0.19745(12) -0.00697(9) 0.0216(2) Uani 1 1 d . . . H6 H -0.1587 0.2456 -0.0452 0.026 Uiso 1 1 calc R . . C7 C -0.03672(14) 0.07042(12) -0.03470(8) 0.0207(2) Uani 1 1 d . . . H7 H -0.0718 0.0348 -0.0918 0.025 Uiso 1 1 calc R . . C8 C 0.06268(13) -0.00090(11) 0.01964(7) 0.0180(2) Uani 1 1 d . . . H8 H 0.0961 -0.0855 -0.0001 0.022 Uiso 1 1 calc R . . C8A C 0.11719(12) 0.05011(11) 0.10597(7) 0.01459(19) Uani 1 1 d . . . C9 C 0.21535(12) -0.02150(10) 0.16551(7) 0.01426(19) Uani 1 1 d . . . C9A C 0.26784(12) 0.03077(10) 0.24976(7) 0.01430(18) Uani 1 1 d . . . C10 C 0.11518(13) 0.22997(11) 0.21811(8) 0.0159(2) Uani 1 1 d . . . H10 H 0.0799 0.3147 0.2365 0.019 Uiso 1 1 calc R . . C10A C 0.06549(12) 0.17889(10) 0.13368(8) 0.01509(19) Uani 1 1 d . . . C11 C 0.26723(12) -0.15656(10) 0.13735(8) 0.01574(19) Uani 1 1 d . . . O1 O 0.36521(11) -0.17847(9) 0.07974(7) 0.0298(2) Uani 1 1 d . . . O2 O 0.18976(10) -0.24839(8) 0.18471(7) 0.02229(18) Uani 1 1 d . . . C12 C 0.23394(15) -0.38603(11) 0.16980(9) 0.0231(2) Uani 1 1 d . . . H12A H 0.3019 -0.3935 0.1145 0.028 Uiso 1 1 calc R . . H12B H 0.1386 -0.4400 0.1596 0.028 Uiso 1 1 calc R . . C13 C 0.32064(15) -0.43418(12) 0.25361(9) 0.0247(2) Uani 1 1 d . . . H13A H 0.4182 -0.3840 0.2609 0.037 Uiso 1 1 calc R . . H13B H 0.3456 -0.5277 0.2461 0.037 Uiso 1 1 calc R . . H13C H 0.2547 -0.4223 0.3085 0.037 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 C1 0.0173(5) 0.0167(5) 0.0163(5) 0.0011(4) 0.0006(4) 0.0015(4) C2 0.0184(5) 0.0207(5) 0.0160(5) 0.0025(4) -0.0019(4) 0.0007(4) C3 0.0210(5) 0.0218(5) 0.0145(5) -0.0015(4) -0.0017(4) -0.0015(4) C4 0.0199(5) 0.0167(5) 0.0153(5) -0.0025(4) 0.0002(4) 0.0003(4) C4A 0.0160(5) 0.0146(5) 0.0138(4) -0.0011(4) 0.0006(3) -0.0003(4) C5 0.0192(5) 0.0189(5) 0.0189(5) 0.0019(4) -0.0008(4) 0.0018(4) C6 0.0202(5) 0.0248(6) 0.0197(5) 0.0034(4) -0.0040(4) 0.0001(4) C7 0.0207(5) 0.0255(5) 0.0157(5) -0.0007(4) -0.0021(4) -0.0038(4) C8 0.0195(5) 0.0189(5) 0.0156(5) -0.0024(4) -0.0007(4) -0.0019(4) C8A 0.0148(4) 0.0161(4) 0.0128(4) -0.0007(4) 0.0005(4) -0.0013(3) C9 0.0151(4) 0.0135(4) 0.0142(4) -0.0010(4) 0.0021(4) -0.0006(3) C9A 0.0148(4) 0.0149(4) 0.0132(4) 0.0006(3) 0.0018(4) -0.0004(3) C10 0.0164(5) 0.0153(5) 0.0160(5) -0.0012(4) 0.0003(4) 0.0009(3) C10A 0.0143(4) 0.0163(5) 0.0147(4) 0.0006(4) 0.0004(4) -0.0009(3) C11 0.0162(4) 0.0166(5) 0.0144(4) -0.0013(4) -0.0011(4) 0.0005(4) O1 0.0329(5) 0.0229(4) 0.0337(5) -0.0042(4) 0.0172(4) 0.0000(4) O2 0.0271(4) 0.0143(3) 0.0255(4) -0.0008(3) 0.0093(4) 0.0018(3) C12 0.0293(6) 0.0131(5) 0.0269(6) -0.0017(4) 0.0038(5) 0.0026(4) C13 0.0247(6) 0.0213(5) 0.0280(6) 0.0020(5) 0.0046(5) 0.0041(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 C2 1.3673(16) . ? C1 C9A 1.4271(15) . ? C1 H1 0.9500 . ? C2 C3 1.4252(16) . ? C2 H2 0.9500 . ? C3 C4 1.3615(16) . ? C3 H3 0.9500 . ? C4 C4A 1.4274(15) . ? C4 H4 0.9500 . ? C4A C10 1.3956(15) . ? C4A C9A 1.4375(14) . ? C5 C6 1.3614(17) . ? C5 C10A 1.4278(15) . ? C5 H5 0.9500 . ? C6 C7 1.4226(17) . ? C6 H6 0.9500 . ? C7 C8 1.3634(16) . ? C7 H7 0.9500 . ? C8 C8A 1.4296(14) . ? C8 H8 0.9500 . ? C8A C9 1.4034(14) . ? C8A C10A 1.4385(15) . ? C9 C9A 1.4027(14) . ? C9 C11 1.4990(14) . ? C10 C10A 1.3930(15) . ? C10 H10 0.9500 . ? C11 O1 1.1996(14) . ? C11 O2 1.3325(13) . ? O2 C12 1.4651(13) . ? C12 C13 1.5013(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.66(10) . . ? C2 C1 H1 119.7 . . ? C9A C1 H1 119.7 . . ? C1 C2 C3 120.72(11) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.22(11) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C4A 120.95(10) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C10 C4A C4 121.50(10) . . ? C10 C4A C9A 119.65(9) . . ? C4 C4A C9A 118.85(10) . . ? C6 C5 C10A 120.98(10) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 120.20(11) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.83(11) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 120.79(10) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C9 C8A C8 122.75(10) . . ? C9 C8A C10A 118.89(9) . . ? C8 C8A C10A 118.34(10) . . ? C9A C9 C8A 121.75(9) . . ? C9A C9 C11 119.32(9) . . ? C8A C9 C11 118.93(10) . . ? C9 C9A C1 122.76(9) . . ? C9 C9A C4A 118.66(9) . . ? C1 C9A C4A 118.57(10) . . ? C10A C10 C4A 121.61(10) . . ? C10A C10 H10 119.2 . . ? C4A C10 H10 119.2 . . ? C10 C10A C5 121.72(10) . . ? C10 C10A C8A 119.42(10) . . ? C5 C10A C8A 118.85(10) . . ? O1 C11 O2 124.80(10) . . ? O1 C11 C9 124.30(10) . . ? O2 C11 C9 110.90(9) . . ? C11 O2 C12 117.83(9) . . ? O2 C12 C13 108.58(10) . . ? O2 C12 H12A 110.0 . . ? C13 C12 H12A 110.0 . . ? O2 C12 H12B 110.0 . . ? C13 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C9A C1 C2 C3 0.84(17) . . . . ? C1 C2 C3 C4 -0.47(18) . . . . ? C2 C3 C4 C4A -0.87(17) . . . . ? C3 C4 C4A C10 -178.18(11) . . . . ? C3 C4 C4A C9A 1.79(16) . . . . ? C10A C5 C6 C7 -1.02(18) . . . . ? C5 C6 C7 C8 0.66(18) . . . . ? C6 C7 C8 C8A 0.09(18) . . . . ? C7 C8 C8A C9 177.85(11) . . . . ? C7 C8 C8A C10A -0.46(16) . . . . ? C8 C8A C9 C9A 179.77(10) . . . . ? C10A C8A C9 C9A -1.93(14) . . . . ? C8 C8A C9 C11 0.75(15) . . . . ? C10A C8A C9 C11 179.05(9) . . . . ? C8A C9 C9A C1 -177.11(10) . . . . ? C11 C9 C9A C1 1.91(15) . . . . ? C8A C9 C9A C4A 1.73(14) . . . . ? C11 C9 C9A C4A -179.25(9) . . . . ? C2 C1 C9A C9 178.95(10) . . . . ? C2 C1 C9A C4A 0.11(15) . . . . ? C10 C4A C9A C9 -0.31(15) . . . . ? C4 C4A C9A C9 179.71(10) . . . . ? C10 C4A C9A C1 178.58(10) . . . . ? C4 C4A C9A C1 -1.39(14) . . . . ? C4 C4A C10 C10A 179.09(10) . . . . ? C9A C4A C10 C10A -0.88(16) . . . . ? C4A C10 C10A C5 179.63(10) . . . . ? C4A C10 C10A C8A 0.68(16) . . . . ? C6 C5 C10A C10 -178.32(11) . . . . ? C6 C5 C10A C8A 0.64(16) . . . . ? C9 C8A C10A C10 0.71(14) . . . . ? C8 C8A C10A C10 179.09(9) . . . . ? C9 C8A C10A C5 -178.27(10) . . . . ? C8 C8A C10A C5 0.11(15) . . . . ? C9A C9 C11 O1 -104.24(14) . . . . ? C8A C9 C11 O1 74.81(15) . . . . ? C9A C9 C11 O2 75.89(12) . . . . ? C8A C9 C11 O2 -105.07(11) . . . . ? O1 C11 O2 C12 4.05(17) . . . . ? C9 C11 O2 C12 -176.08(10) . . . . ? C11 O2 C12 C13 107.51(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.374 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.042 # Attachment 'cb23_0m_IPAE.cif' data_cb23_0m _database_code_depnum_ccdc_archive 'CCDC 808571' #TrackingRef 'cb23_0m_IPAE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O2' _chemical_formula_weight 264.31 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.5454(12) _cell_length_b 7.5826(5) _cell_length_c 22.0553(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.2065(11) _cell_angle_gamma 90.00 _cell_volume 2755.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4794 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 28.31 _exptl_crystal_description 'thin plate frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 23259 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3166 _reflns_number_gt 2263 _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^)+(0.0465P)^2^+4.8847P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3166 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.05647(10) 0.7586(2) 0.21923(8) 0.0217(4) Uani 1 1 d . . . H1 H 0.0266 0.8266 0.1887 0.026 Uiso 1 1 calc R . . C2 C 0.02885(11) 0.7440(3) 0.27512(8) 0.0261(4) Uani 1 1 d . . . H2 H -0.0196 0.8031 0.2834 0.031 Uiso 1 1 calc R . . C3 C 0.07159(11) 0.6415(3) 0.32126(8) 0.0270(4) Uani 1 1 d . . . H3 H 0.0514 0.6317 0.3601 0.032 Uiso 1 1 calc R . . C4 C 0.14118(11) 0.5572(2) 0.31043(8) 0.0246(4) Uani 1 1 d . . . H4 H 0.1692 0.4889 0.3418 0.030 Uiso 1 1 calc R . . C4A C 0.17302(11) 0.5697(2) 0.25225(8) 0.0206(4) Uani 1 1 d . . . C5 C 0.35100(11) 0.4225(2) 0.17150(9) 0.0245(4) Uani 1 1 d . . . H5 H 0.3793 0.3513 0.2019 0.029 Uiso 1 1 calc R . . C6 C 0.38188(11) 0.4434(3) 0.11694(9) 0.0281(4) Uani 1 1 d . . . H6 H 0.4314 0.3872 0.1096 0.034 Uiso 1 1 calc R . . C7 C 0.34048(11) 0.5486(3) 0.07100(9) 0.0268(4) Uani 1 1 d . . . H7 H 0.3624 0.5623 0.0329 0.032 Uiso 1 1 calc R . . C8 C 0.26950(10) 0.6303(2) 0.08095(8) 0.0214(4) Uani 1 1 d . . . H8 H 0.2426 0.7008 0.0497 0.026 Uiso 1 1 calc R . . C8A C 0.23512(10) 0.6116(2) 0.13755(8) 0.0184(4) Uani 1 1 d . . . C9 C 0.16169(10) 0.6916(2) 0.14916(8) 0.0175(4) Uani 1 1 d . . . C9A C 0.12965(10) 0.6733(2) 0.20557(8) 0.0183(4) Uani 1 1 d . . . C10 C 0.24525(11) 0.4880(2) 0.24016(8) 0.0218(4) Uani 1 1 d . . . H10 H 0.2736 0.4184 0.2710 0.026 Uiso 1 1 calc R . . C10A C 0.27694(10) 0.5056(2) 0.18414(8) 0.0206(4) Uani 1 1 d . . . C11 C 0.11507(10) 0.7966(2) 0.10013(8) 0.0174(3) Uani 1 1 d . . . O1 O 0.05924(7) 0.73935(17) 0.06713(6) 0.0253(3) Uani 1 1 d . . . O2 O 0.14234(7) 0.96242(16) 0.09805(6) 0.0229(3) Uani 1 1 d . . . C12 C 0.09837(11) 1.0816(2) 0.05371(8) 0.0222(4) Uani 1 1 d . . . H12 H 0.0388 1.0581 0.0529 0.027 Uiso 1 1 calc R . . C13 C 0.11585(16) 1.2647(3) 0.07742(11) 0.0411(6) Uani 1 1 d . . . H13A H 0.1011 1.2733 0.1194 0.062 Uiso 1 1 calc R . . H13B H 0.0840 1.3501 0.0518 0.062 Uiso 1 1 calc R . . H13C H 0.1738 1.2903 0.0765 0.062 Uiso 1 1 calc R . . C14 C 0.12558(11) 1.0498(3) -0.00893(9) 0.0293(4) Uani 1 1 d . . . H14A H 0.1833 1.0789 -0.0088 0.044 Uiso 1 1 calc R . . H14B H 0.0939 1.1243 -0.0386 0.044 Uiso 1 1 calc R . . H14C H 0.1172 0.9255 -0.0200 0.044 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 C1 0.0187(8) 0.0207(9) 0.0250(9) -0.0013(7) -0.0024(7) -0.0036(7) C2 0.0198(8) 0.0297(10) 0.0283(10) -0.0063(8) 0.0006(7) -0.0046(8) C3 0.0275(10) 0.0315(11) 0.0221(9) -0.0022(8) 0.0032(7) -0.0117(8) C4 0.0302(10) 0.0203(9) 0.0222(9) 0.0015(7) -0.0041(7) -0.0095(8) C4A 0.0222(8) 0.0147(8) 0.0241(9) 0.0007(7) -0.0030(7) -0.0066(7) C5 0.0229(9) 0.0169(9) 0.0317(10) -0.0038(7) -0.0084(7) 0.0039(7) C6 0.0216(9) 0.0261(10) 0.0355(11) -0.0108(8) -0.0035(8) 0.0049(8) C7 0.0250(9) 0.0298(11) 0.0251(9) -0.0077(8) 0.0003(7) 0.0018(8) C8 0.0208(8) 0.0208(9) 0.0217(9) -0.0022(7) -0.0031(7) 0.0013(7) C8A 0.0173(8) 0.0131(8) 0.0238(9) -0.0030(7) -0.0041(7) -0.0012(6) C9 0.0177(8) 0.0133(8) 0.0207(8) -0.0012(7) -0.0030(6) -0.0036(6) C9A 0.0180(8) 0.0147(8) 0.0216(8) -0.0010(7) -0.0022(6) -0.0043(6) C10 0.0260(9) 0.0142(8) 0.0233(9) 0.0026(7) -0.0076(7) -0.0023(7) C10A 0.0210(8) 0.0129(8) 0.0266(9) -0.0026(7) -0.0047(7) -0.0010(7) C11 0.0159(8) 0.0161(8) 0.0201(8) 0.0003(7) 0.0004(6) 0.0006(6) O1 0.0215(6) 0.0208(7) 0.0315(7) 0.0029(5) -0.0092(5) -0.0049(5) O2 0.0220(6) 0.0177(6) 0.0273(7) 0.0051(5) -0.0067(5) -0.0037(5) C12 0.0198(8) 0.0171(9) 0.0287(10) 0.0074(7) -0.0030(7) -0.0002(7) C13 0.0579(15) 0.0206(11) 0.0434(13) 0.0052(9) -0.0032(11) -0.0049(10) C14 0.0194(9) 0.0362(12) 0.0317(10) 0.0106(9) -0.0003(7) 0.0011(8) _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 C2 1.358(3) . ? C1 C9A 1.429(2) . ? C1 H1 0.9500 . ? C2 C3 1.418(3) . ? C2 H2 0.9500 . ? C3 C4 1.357(3) . ? C3 H3 0.9500 . ? C4 C4A 1.434(3) . ? C4 H4 0.9500 . ? C4A C10 1.393(3) . ? C4A C9A 1.434(2) . ? C5 C6 1.359(3) . ? C5 C10A 1.427(2) . ? C5 H5 0.9500 . ? C6 C7 1.416(3) . ? C6 H6 0.9500 . ? C7 C8 1.363(3) . ? C7 H7 0.9500 . ? C8 C8A 1.425(2) . ? C8 H8 0.9500 . ? C8A C9 1.402(2) . ? C8A C10A 1.432(2) . ? C9 C9A 1.403(2) . ? C9 C11 1.499(2) . ? C10 C10A 1.392(3) . ? C10 H10 0.9500 . ? C11 O1 1.204(2) . ? C11 O2 1.338(2) . ? O2 C12 1.474(2) . ? C12 C13 1.503(3) . ? C12 C14 1.511(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 121.08(17) . . ? C2 C1 H1 119.5 . . ? C9A C1 H1 119.5 . . ? C1 C2 C3 120.61(17) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.53(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 120.85(17) . . ? C3 C4 H4 119.6 . . ? C4A C4 H4 119.6 . . ? C10 C4A C4 122.21(16) . . ? C10 C4A C9A 119.21(16) . . ? C4 C4A C9A 118.57(16) . . ? C6 C5 C10A 121.35(17) . . ? C6 C5 H5 119.3 . . ? C10A C5 H5 119.3 . . ? C5 C6 C7 120.18(17) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.59(18) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 120.90(17) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C9 C8A C8 122.54(16) . . ? C9 C8A C10A 118.81(16) . . ? C8 C8A C10A 118.64(16) . . ? C8A C9 C9A 121.48(16) . . ? C8A C9 C11 119.73(15) . . ? C9A C9 C11 118.78(15) . . ? C9 C9A C1 122.52(16) . . ? C9 C9A C4A 119.10(16) . . ? C1 C9A C4A 118.35(16) . . ? C10A C10 C4A 121.74(16) . . ? C10A C10 H10 119.1 . . ? C4A C10 H10 119.1 . . ? C10 C10A C5 122.03(17) . . ? C10 C10A C8A 119.62(16) . . ? C5 C10A C8A 118.34(16) . . ? O1 C11 O2 124.10(16) . . ? O1 C11 C9 124.13(16) . . ? O2 C11 C9 111.76(14) . . ? C11 O2 C12 116.81(13) . . ? O2 C12 C13 105.53(15) . . ? O2 C12 C14 109.80(15) . . ? C13 C12 C14 113.69(17) . . ? O2 C12 H12 109.2 . . ? C13 C12 H12 109.2 . . ? C14 C12 H12 109.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C9A C1 C2 C3 -0.8(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C4A 0.0(3) . . . . ? C3 C4 C4A C10 178.52(17) . . . . ? C3 C4 C4A C9A -0.1(3) . . . . ? C10A C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C8A -0.2(3) . . . . ? C7 C8 C8A C9 -179.11(17) . . . . ? C7 C8 C8A C10A 0.4(3) . . . . ? C8 C8A C9 C9A -179.08(16) . . . . ? C10A C8A C9 C9A 1.5(2) . . . . ? C8 C8A C9 C11 2.1(2) . . . . ? C10A C8A C9 C11 -177.33(15) . . . . ? C8A C9 C9A C1 177.74(16) . . . . ? C11 C9 C9A C1 -3.5(2) . . . . ? C8A C9 C9A C4A -0.2(2) . . . . ? C11 C9 C9A C4A 178.61(15) . . . . ? C2 C1 C9A C9 -177.23(17) . . . . ? C2 C1 C9A C4A 0.7(3) . . . . ? C10 C4A C9A C9 -0.9(2) . . . . ? C4 C4A C9A C9 177.77(15) . . . . ? C10 C4A C9A C1 -178.90(16) . . . . ? C4 C4A C9A C1 -0.2(2) . . . . ? C4 C4A C10 C10A -177.94(16) . . . . ? C9A C4A C10 C10A 0.7(3) . . . . ? C4A C10 C10A C5 179.85(17) . . . . ? C4A C10 C10A C8A 0.6(3) . . . . ? C6 C5 C10A C10 -178.88(17) . . . . ? C6 C5 C10A C8A 0.4(3) . . . . ? C9 C8A C10A C10 -1.7(2) . . . . ? C8 C8A C10A C10 178.84(16) . . . . ? C9 C8A C10A C5 179.07(16) . . . . ? C8 C8A C10A C5 -0.4(2) . . . . ? C8A C9 C11 O1 96.8(2) . . . . ? C9A C9 C11 O1 -82.0(2) . . . . ? C8A C9 C11 O2 -84.04(19) . . . . ? C9A C9 C11 O2 97.14(18) . . . . ? O1 C11 O2 C12 2.3(2) . . . . ? C9 C11 O2 C12 -176.84(14) . . . . ? C11 O2 C12 C13 156.82(16) . . . . ? C11 O2 C12 C14 -80.27(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.050 # Attachment 'cb24_0m_C4.cif' data_cb24_0m _database_code_depnum_ccdc_archive 'CCDC 808572' #TrackingRef 'cb24_0m_C4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 O2' _chemical_formula_weight 278.33 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 P2(1)/c 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 9.783(3) _cell_length_b 8.098(3) _cell_length_c 19.488(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.331(5) _cell_angle_gamma 90.00 _cell_volume 1531.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4476 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 23.64 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 16430 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2898 _reflns_number_gt 2002 _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^)+(0.0615P)^2^+0.1911P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2898 _refine_ls_number_parameters 247 _refine_ls_number_restraints 178 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.010 _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 0.07640(18) 0.7127(2) 0.18989(8) 0.0764(4) Uani 1 1 d . . . H1A H 0.1363 0.6589 0.2235 0.092 Uiso 1 1 calc R . . C2 C -0.0242(2) 0.8088(2) 0.20931(9) 0.0881(5) Uani 1 1 d . . . H2A H -0.0326 0.8198 0.2561 0.106 Uiso 1 1 calc R . . C3 C -0.1167(2) 0.8927(2) 0.16041(9) 0.0861(5) Uani 1 1 d . . . H3A H -0.1854 0.9588 0.1749 0.103 Uiso 1 1 calc R . . C4 C -0.10583(16) 0.87733(19) 0.09231(8) 0.0735(4) Uani 1 1 d . . . H4A H -0.1678 0.9330 0.0602 0.088 Uiso 1 1 calc R . . C5 C 0.12893(17) 0.6552(2) -0.09613(8) 0.0759(4) Uani 1 1 d . . . H5A H 0.0682 0.7125 -0.1282 0.091 Uiso 1 1 calc R . . C6 C 0.2283(2) 0.5634(2) -0.11823(9) 0.0880(5) Uani 1 1 d . . . H6A H 0.2357 0.5573 -0.1653 0.106 Uiso 1 1 calc R . . C7 C 0.32185(18) 0.4758(2) -0.07035(10) 0.0886(5) Uani 1 1 d . . . H7A H 0.3908 0.4126 -0.0862 0.106 Uiso 1 1 calc R . . C8 C 0.31233(16) 0.4826(2) -0.00164(9) 0.0773(4) Uani 1 1 d . . . H8A H 0.3748 0.4235 0.0290 0.093 Uiso 1 1 calc R . . C9 C 0.19487(14) 0.59279(17) 0.09554(7) 0.0628(4) Uani 1 1 d . A . C10 C 0.01145(15) 0.76237(17) -0.00103(7) 0.0645(4) Uani 1 1 d . . . H10A H -0.0506 0.8177 -0.0332 0.077 Uiso 1 1 calc R . . C4A C -0.00162(14) 0.77790(16) 0.06865(7) 0.0605(4) Uani 1 1 d . . . C8A C 0.20841(14) 0.57854(17) 0.02454(7) 0.0622(4) Uani 1 1 d . . . C9A C 0.09293(14) 0.69197(17) 0.11850(7) 0.0604(4) Uani 1 1 d . . . C10A C 0.11420(14) 0.66697(17) -0.02459(7) 0.0620(4) Uani 1 1 d . . . C11 C 0.29356(17) 0.5024(2) 0.14757(8) 0.0762(4) Uani 1 1 d DU . . O1 O 0.3779(4) 0.5695(5) 0.1885(2) 0.1295(15) Uani 0.776(5) 1 d PDU A 1 O2 O 0.2627(6) 0.3430(4) 0.1471(4) 0.0867(17) Uani 0.776(5) 1 d PDU A 1 C12 C 0.3526(9) 0.2386(8) 0.1951(3) 0.0973(16) Uani 0.776(5) 1 d PDU A 1 H12A H 0.3320 0.2542 0.2420 0.117 Uiso 0.776(5) 1 calc PR A 1 H12B H 0.4485 0.2671 0.1935 0.117 Uiso 0.776(5) 1 calc PR A 1 C13 C 0.3269(4) 0.0641(3) 0.17321(16) 0.0980(9) Uani 0.776(5) 1 d PDU A 1 H13A H 0.3758 -0.0073 0.2080 0.118 Uiso 0.776(5) 1 calc PR A 1 H13C H 0.2293 0.0415 0.1721 0.118 Uiso 0.776(5) 1 calc PR A 1 C14 C 0.3679(3) 0.0202(5) 0.10592(17) 0.0994(9) Uani 0.776(5) 1 d PDU A 1 H14A H 0.3353 0.1057 0.0730 0.119 Uiso 0.776(5) 1 calc PR A 1 H14B H 0.3216 -0.0816 0.0904 0.119 Uiso 0.776(5) 1 calc PR A 1 C15 C 0.5187(4) -0.0019(10) 0.1043(3) 0.179(3) Uani 0.776(5) 1 d PDU A 1 H15A H 0.5360 -0.0201 0.0575 0.269 Uiso 0.776(5) 1 calc PR A 1 H15B H 0.5506 -0.0954 0.1322 0.269 Uiso 0.776(5) 1 calc PR A 1 H15C H 0.5668 0.0954 0.1222 0.269 Uiso 0.776(5) 1 calc PR A 1 O1D O 0.4139(8) 0.5354(16) 0.1637(6) 0.094(3) Uani 0.224(5) 1 d PDU A 2 O2D O 0.2599(17) 0.3502(14) 0.1619(14) 0.069(3) Uani 0.224(5) 1 d PDU A 2 C12D C 0.343(3) 0.245(3) 0.2118(9) 0.095(4) Uani 0.224(5) 1 d PDU A 2 H12C H 0.2855 0.1797 0.2383 0.114 Uiso 0.224(5) 1 calc PR A 2 H12D H 0.4061 0.3105 0.2434 0.114 Uiso 0.224(5) 1 calc PR A 2 C13D C 0.4194(18) 0.139(2) 0.1685(5) 0.140(5) Uani 0.224(5) 1 d PDU A 2 H13B H 0.5119 0.1646 0.1899 0.168 Uiso 0.224(5) 1 calc PR A 2 H13D H 0.3998 0.0333 0.1889 0.168 Uiso 0.224(5) 1 calc PR A 2 C14D C 0.454(3) 0.0790(12) 0.1054(7) 0.128(5) Uani 0.224(5) 1 d PDU A 2 H14C H 0.5474 0.1154 0.1034 0.154 Uiso 0.224(5) 1 calc PR A 2 H14D H 0.3965 0.1413 0.0701 0.154 Uiso 0.224(5) 1 calc PR A 2 C15D C 0.4486(18) -0.0932(12) 0.0802(8) 0.125(4) Uani 0.224(5) 1 d PDU A 2 H15D H 0.3621 -0.1127 0.0521 0.187 Uiso 0.224(5) 1 calc PR A 2 H15E H 0.4580 -0.1674 0.1189 0.187 Uiso 0.224(5) 1 calc PR A 2 H15F H 0.5226 -0.1113 0.0531 0.187 Uiso 0.224(5) 1 calc PR A 2 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 0.0897(11) 0.0780(10) 0.0580(8) 0.0062(7) -0.0035(8) -0.0069(9) C2 0.1063(13) 0.0968(13) 0.0610(9) -0.0085(9) 0.0103(9) -0.0029(11) C3 0.0947(12) 0.0864(11) 0.0772(11) -0.0141(9) 0.0112(9) 0.0041(9) C4 0.0791(10) 0.0668(9) 0.0722(10) 0.0002(7) 0.0004(7) 0.0039(8) C5 0.0834(10) 0.0835(10) 0.0592(9) -0.0051(8) 0.0030(7) -0.0079(9) C6 0.0939(12) 0.1023(13) 0.0688(10) -0.0159(9) 0.0147(9) -0.0174(10) C7 0.0743(10) 0.0939(12) 0.1004(13) -0.0245(10) 0.0216(9) -0.0092(9) C8 0.0634(9) 0.0777(10) 0.0894(12) -0.0073(8) 0.0036(8) -0.0039(8) C9 0.0649(8) 0.0575(8) 0.0621(8) 0.0035(6) -0.0066(6) -0.0080(6) C10 0.0702(9) 0.0621(8) 0.0578(8) 0.0057(6) -0.0047(6) -0.0014(7) C4A 0.0664(8) 0.0546(7) 0.0584(8) 0.0026(6) 0.0005(6) -0.0068(6) C8A 0.0586(8) 0.0592(8) 0.0667(9) -0.0027(6) -0.0001(6) -0.0105(6) C9A 0.0670(8) 0.0555(8) 0.0560(8) 0.0019(6) -0.0020(6) -0.0096(6) C10A 0.0659(8) 0.0609(8) 0.0571(8) 0.0004(6) 0.0000(6) -0.0126(7) C11 0.0754(10) 0.0750(11) 0.0729(10) 0.0033(8) -0.0110(8) 0.0004(8) O1 0.132(2) 0.0995(16) 0.133(3) -0.0113(18) -0.076(2) 0.0054(18) O2 0.101(2) 0.0720(15) 0.080(3) 0.0079(11) -0.0170(15) 0.0160(13) C12 0.124(3) 0.094(2) 0.068(3) 0.014(2) -0.007(2) 0.043(2) C13 0.099(2) 0.0784(17) 0.116(2) 0.0316(15) 0.0148(16) 0.0119(14) C14 0.101(2) 0.0767(19) 0.118(2) 0.0045(16) 0.0043(17) 0.0031(16) C15 0.124(3) 0.228(8) 0.186(5) 0.026(5) 0.022(3) 0.058(4) O1D 0.064(4) 0.107(8) 0.105(7) 0.022(5) -0.005(3) -0.022(4) O2D 0.061(5) 0.072(5) 0.067(8) 0.023(5) -0.015(4) -0.011(4) C12D 0.109(9) 0.105(8) 0.065(7) 0.027(5) -0.008(5) 0.012(6) C13D 0.171(11) 0.139(10) 0.094(6) 0.012(6) -0.043(7) 0.076(8) C14D 0.168(15) 0.084(7) 0.129(8) 0.008(6) 0.002(10) 0.014(9) C15D 0.129(10) 0.080(6) 0.164(11) -0.004(6) 0.014(9) -0.004(6) _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 C2 1.346(2) . ? C1 C9A 1.431(2) . ? C1 H1A 0.9300 . ? C2 C3 1.403(2) . ? C2 H2A 0.9300 . ? C3 C4 1.351(2) . ? C3 H3A 0.9300 . ? C4 C4A 1.421(2) . ? C4 H4A 0.9300 . ? C5 C6 1.337(2) . ? C5 C10A 1.423(2) . ? C5 H5A 0.9300 . ? C6 C7 1.412(3) . ? C6 H6A 0.9300 . ? C7 C8 1.355(2) . ? C7 H7A 0.9300 . ? C8 C8A 1.425(2) . ? C8 H8A 0.9300 . ? C9 C9A 1.398(2) . ? C9 C8A 1.411(2) . ? C9 C11 1.499(2) . ? C10 C4A 1.386(2) . ? C10 C10A 1.391(2) . ? C10 H10A 0.9300 . ? C4A C9A 1.4332(19) . ? C8A C10A 1.4331(19) . ? C11 O1 1.202(3) . ? C11 O1D 1.209(7) . ? C11 O2D 1.314(8) . ? C11 O2 1.325(4) . ? O2 C12 1.468(3) . ? C12 C13 1.488(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.463(4) . ? C13 H13A 0.9700 . ? C13 H13C 0.9700 . ? C14 C15 1.491(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O2D C12D 1.461(8) . ? C12D C13D 1.472(11) . ? C12D H12C 0.9700 . ? C12D H12D 0.9700 . ? C13D C14D 1.400(9) . ? C13D H13B 0.9700 . ? C13D H13D 0.9700 . ? C14D C15D 1.477(9) . ? C14D H14C 0.9700 . ? C14D H14D 0.9700 . ? C15D H15D 0.9600 . ? C15D H15E 0.9600 . ? C15D H15F 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 C2 C1 C9A 121.24(15) . . ? C2 C1 H1A 119.4 . . ? C9A C1 H1A 119.4 . . ? C1 C2 C3 121.34(16) . . ? C1 C2 H2A 119.3 . . ? C3 C2 H2A 119.3 . . ? C4 C3 C2 119.87(17) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C4A 121.37(15) . . ? C3 C4 H4A 119.3 . . ? C4A C4 H4A 119.3 . . ? C6 C5 C10A 121.42(16) . . ? C6 C5 H5A 119.3 . . ? C10A C5 H5A 119.3 . . ? C5 C6 C7 120.19(16) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C8 C7 C6 120.79(17) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C8A 121.21(16) . . ? C7 C8 H8A 119.4 . . ? C8A C8 H8A 119.4 . . ? C9A C9 C8A 121.39(12) . . ? C9A C9 C11 119.23(13) . . ? C8A C9 C11 119.37(14) . . ? C4A C10 C10A 122.32(13) . . ? C4A C10 H10A 118.8 . . ? C10A C10 H10A 118.8 . . ? C10 C4A C4 121.93(13) . . ? C10 C4A C9A 119.20(13) . . ? C4 C4A C9A 118.87(13) . . ? C9 C8A C8 123.79(14) . . ? C9 C8A C10A 118.77(13) . . ? C8 C8A C10A 117.43(14) . . ? C9 C9A C1 123.54(13) . . ? C9 C9A C4A 119.15(13) . . ? C1 C9A C4A 117.30(14) . . ? C10 C10A C5 121.90(14) . . ? C10 C10A C8A 119.14(13) . . ? C5 C10A C8A 118.96(14) . . ? O1 C11 O1D 33.3(5) . . ? O1 C11 O2D 116.9(10) . . ? O1D C11 O2D 114.4(10) . . ? O1 C11 O2 125.6(4) . . ? O1D C11 O2 115.5(7) . . ? O2D C11 O2 13.0(16) . . ? O1 C11 C9 123.8(2) . . ? O1D C11 C9 126.1(6) . . ? O2D C11 C9 116.4(8) . . ? O2 C11 C9 110.1(3) . . ? C11 O2 C12 116.0(5) . . ? O2 C12 C13 107.4(5) . . ? O2 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? O2 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 C12 115.6(4) . . ? C14 C13 H13A 108.4 . . ? C12 C13 H13A 108.4 . . ? C14 C13 H13C 108.4 . . ? C12 C13 H13C 108.4 . . ? H13A C13 H13C 107.4 . . ? C13 C14 C15 115.7(4) . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C11 O2D C12D 123.7(17) . . ? O2D C12D C13D 103.9(14) . . ? O2D C12D H12C 111.0 . . ? C13D C12D H12C 111.0 . . ? O2D C12D H12D 111.0 . . ? C13D C12D H12D 111.0 . . ? H12C C12D H12D 109.0 . . ? C14D C13D C12D 154.0(13) . . ? C14D C13D H13B 98.0 . . ? C12D C13D H13B 98.0 . . ? C14D C13D H13D 98.0 . . ? C12D C13D H13D 98.0 . . ? H13B C13D H13D 103.7 . . ? C13D C14D C15D 128.0(14) . . ? C13D C14D H14C 105.3 . . ? C15D C14D H14C 105.3 . . ? C13D C14D H14D 105.3 . . ? C15D C14D H14D 105.3 . . ? H14C C14D H14D 106.0 . . ? C14D C15D H15D 109.5 . . ? C14D C15D H15E 109.5 . . ? H15D C15D H15E 109.5 . . ? C14D C15D H15F 109.5 . . ? H15D C15D H15F 109.5 . . ? H15E C15D H15F 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 C9A C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C4A -0.3(3) . . . . ? C10A C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C8A -0.3(3) . . . . ? C10A C10 C4A C4 179.17(13) . . . . ? C10A C10 C4A C9A -0.5(2) . . . . ? C3 C4 C4A C10 -179.37(14) . . . . ? C3 C4 C4A C9A 0.3(2) . . . . ? C9A C9 C8A C8 178.42(13) . . . . ? C11 C9 C8A C8 -0.3(2) . . . . ? C9A C9 C8A C10A -0.61(19) . . . . ? C11 C9 C8A C10A -179.38(12) . . . . ? C7 C8 C8A C9 -178.83(14) . . . . ? C7 C8 C8A C10A 0.2(2) . . . . ? C8A C9 C9A C1 -178.90(13) . . . . ? C11 C9 C9A C1 -0.1(2) . . . . ? C8A C9 C9A C4A 1.4(2) . . . . ? C11 C9 C9A C4A -179.80(12) . . . . ? C2 C1 C9A C9 -179.49(15) . . . . ? C2 C1 C9A C4A 0.2(2) . . . . ? C10 C4A C9A C9 -0.87(19) . . . . ? C4 C4A C9A C9 179.43(12) . . . . ? C10 C4A C9A C1 179.44(13) . . . . ? C4 C4A C9A C1 -0.27(19) . . . . ? C4A C10 C10A C5 -178.37(13) . . . . ? C4A C10 C10A C8A 1.3(2) . . . . ? C6 C5 C10A C10 179.84(15) . . . . ? C6 C5 C10A C8A 0.1(2) . . . . ? C9 C8A C10A C10 -0.77(19) . . . . ? C8 C8A C10A C10 -179.86(13) . . . . ? C9 C8A C10A C5 178.95(12) . . . . ? C8 C8A C10A C5 -0.14(19) . . . . ? C9A C9 C11 O1 -66.7(4) . . . . ? C8A C9 C11 O1 112.1(3) . . . . ? C9A C9 C11 O1D -107.5(7) . . . . ? C8A C9 C11 O1D 71.2(7) . . . . ? C9A C9 C11 O2D 93.3(14) . . . . ? C8A C9 C11 O2D -87.9(14) . . . . ? C9A C9 C11 O2 105.8(4) . . . . ? C8A C9 C11 O2 -75.4(4) . . . . ? O1 C11 O2 C12 -8.5(9) . . . . ? O1D C11 O2 C12 28.6(10) . . . . ? O2D C11 O2 C12 -60(4) . . . . ? C9 C11 O2 C12 179.2(5) . . . . ? C11 O2 C12 C13 -164.4(6) . . . . ? O2 C12 C13 C14 66.0(7) . . . . ? C12 C13 C14 C15 75.9(6) . . . . ? O1 C11 O2D C12D -18(3) . . . . ? O1D C11 O2D C12D 19(3) . . . . ? O2 C11 O2D C12D 117(6) . . . . ? C9 C11 O2D C12D -179.3(17) . . . . ? C11 O2D C12D C13D -100(3) . . . . ? O2D C12D C13D C14D -3(6) . . . . ? C12D C13D C14D C15D -124(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.122 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.028 # Attachment 'cb25r_0m_C3.cif' data_cb25r_0m _database_code_depnum_ccdc_archive 'CCDC 808573' #TrackingRef 'cb25r_0m_C3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O2' _chemical_formula_weight 264.31 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 7.8529(4) _cell_length_b 8.5743(4) _cell_length_c 11.4604(6) _cell_angle_alpha 87.9208(8) _cell_angle_beta 80.4985(8) _cell_angle_gamma 67.0534(7) _cell_volume 700.52(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4910 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 31.19 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 15701 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0121 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 29.57 _reflns_number_total 3918 _reflns_number_gt 2691 _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^)+(0.0849P)^2^+0.0611P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3918 _refine_ls_number_parameters 238 _refine_ls_number_restraints 175 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.043 _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 0.41972(18) 0.52787(15) 0.17202(10) 0.0575(3) Uani 1 1 d . . . H1 H 0.5246 0.4808 0.1139 0.069 Uiso 1 1 calc R . . C2 C 0.2705(2) 0.66461(16) 0.14718(11) 0.0639(3) Uani 1 1 d . . . H2 H 0.2751 0.7107 0.0726 0.077 Uiso 1 1 calc R . . C3 C 0.10848(19) 0.73768(16) 0.23330(12) 0.0640(3) Uani 1 1 d . . . H3 H 0.0056 0.8289 0.2143 0.077 Uiso 1 1 calc R . . C4 C 0.10247(16) 0.67522(15) 0.34346(11) 0.0576(3) Uani 1 1 d . . . H4 H -0.0043 0.7255 0.3998 0.069 Uiso 1 1 calc R . . C4A C 0.25678(15) 0.53386(13) 0.37463(10) 0.0487(2) Uani 1 1 d . . . C5 C 0.39971(18) 0.26140(16) 0.63340(10) 0.0581(3) Uani 1 1 d . A . H5 H 0.2972 0.3147 0.6920 0.070 Uiso 1 1 calc R . . C6 C 0.5432(2) 0.12089(18) 0.65907(11) 0.0666(3) Uani 1 1 d . . . H6 H 0.5377 0.0777 0.7346 0.080 Uiso 1 1 calc R . . C7 C 0.7011(2) 0.03969(17) 0.57180(12) 0.0671(3) Uani 1 1 d . . . H7 H 0.7985 -0.0570 0.5903 0.081 Uiso 1 1 calc R . . C8 C 0.71254(17) 0.10060(15) 0.46153(11) 0.0581(3) Uani 1 1 d . . . H8 H 0.8188 0.0462 0.4057 0.070 Uiso 1 1 calc R . . C8A C 0.56387(15) 0.24719(13) 0.42937(9) 0.0478(2) Uani 1 1 d . A . C9 C 0.56825(15) 0.31315(13) 0.31530(9) 0.0488(3) Uani 1 1 d D . . C9A C 0.41803(15) 0.45520(13) 0.28595(9) 0.0480(2) Uani 1 1 d . A . C10 C 0.25453(15) 0.47007(14) 0.48812(10) 0.0513(3) Uani 1 1 d . A . H10 H 0.1507 0.5232 0.5459 0.062 Uiso 1 1 calc R . . C10A C 0.40333(15) 0.32897(14) 0.51766(9) 0.0483(2) Uani 1 1 d . . . C11 C 0.7427(7) 0.2349(9) 0.2225(6) 0.0544(13) Uani 0.585(7) 1 d PDU A 1 O1 O 0.7537(11) 0.1513(9) 0.1401(5) 0.0856(12) Uani 0.585(7) 1 d PDU A 1 O2 O 0.8910(6) 0.2632(7) 0.2482(3) 0.0811(11) Uani 0.585(7) 1 d PDU A 1 C12 C 1.0680(6) 0.1946(7) 0.1651(4) 0.0917(16) Uani 0.585(7) 1 d PDU A 1 H12A H 1.1722 0.1634 0.2084 0.110 Uiso 0.585(7) 1 calc PR A 1 H12B H 1.0763 0.0932 0.1255 0.110 Uiso 0.585(7) 1 calc PR A 1 C13 C 1.0813(5) 0.3182(4) 0.0772(3) 0.0753(10) Uani 0.585(7) 1 d PDU A 1 H13A H 1.0734 0.4196 0.1166 0.090 Uiso 0.585(7) 1 calc PR A 1 H13B H 0.9774 0.3494 0.0337 0.090 Uiso 0.585(7) 1 calc PR A 1 C14 C 1.2656(7) 0.2454(10) -0.0085(5) 0.0947(15) Uani 0.585(7) 1 d PDU A 1 H14A H 1.2686 0.3255 -0.0687 0.142 Uiso 0.585(7) 1 calc PR A 1 H14B H 1.2761 0.1420 -0.0446 0.142 Uiso 0.585(7) 1 calc PR A 1 H14C H 1.3682 0.2228 0.0337 0.142 Uiso 0.585(7) 1 calc PR A 1 C11D C 0.7242(11) 0.2154(15) 0.2202(10) 0.061(2) Uani 0.415(7) 1 d PDU A 2 O1D O 0.7255(13) 0.1145(12) 0.1533(8) 0.0769(17) Uani 0.415(7) 1 d PDU A 2 O2D O 0.8561(8) 0.2796(9) 0.2130(5) 0.0838(18) Uani 0.415(7) 1 d PDU A 2 C12D C 1.0182(7) 0.2021(10) 0.1205(6) 0.0848(19) Uani 0.415(7) 1 d PDU A 2 H12C H 1.0698 0.0800 0.1280 0.102 Uiso 0.415(7) 1 calc PR A 2 H12D H 0.9805 0.2271 0.0432 0.102 Uiso 0.415(7) 1 calc PR A 2 C13D C 1.1594(7) 0.2689(7) 0.1317(5) 0.0811(15) Uani 0.415(7) 1 d PDU A 2 H13C H 1.2057 0.2334 0.2057 0.097 Uiso 0.415(7) 1 calc PR A 2 H13D H 1.1026 0.3917 0.1337 0.097 Uiso 0.415(7) 1 calc PR A 2 C14D C 1.3221(9) 0.2078(15) 0.0299(7) 0.101(3) Uani 0.415(7) 1 d PDU A 2 H14D H 1.4353 0.1974 0.0570 0.152 Uiso 0.415(7) 1 calc PR A 2 H14E H 1.2985 0.2877 -0.0323 0.152 Uiso 0.415(7) 1 calc PR A 2 H14F H 1.3356 0.0994 0.0005 0.152 Uiso 0.415(7) 1 calc PR A 2 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 0.0627(7) 0.0581(6) 0.0451(6) -0.0002(5) -0.0025(5) -0.0188(5) C2 0.0764(8) 0.0603(7) 0.0518(6) 0.0056(5) -0.0146(6) -0.0219(6) C3 0.0631(7) 0.0536(6) 0.0690(8) 0.0043(5) -0.0175(6) -0.0137(5) C4 0.0498(6) 0.0516(6) 0.0646(7) -0.0036(5) -0.0032(5) -0.0144(5) C4A 0.0477(5) 0.0476(5) 0.0504(6) -0.0027(4) -0.0036(4) -0.0197(4) C5 0.0629(7) 0.0684(7) 0.0451(6) 0.0012(5) -0.0029(5) -0.0301(6) C6 0.0796(8) 0.0748(8) 0.0490(6) 0.0128(6) -0.0147(6) -0.0334(7) C7 0.0760(8) 0.0597(7) 0.0603(7) 0.0086(5) -0.0199(6) -0.0177(6) C8 0.0596(6) 0.0518(6) 0.0539(6) -0.0014(5) -0.0067(5) -0.0129(5) C8A 0.0519(6) 0.0462(5) 0.0455(5) -0.0011(4) -0.0055(4) -0.0199(4) C9 0.0506(5) 0.0485(5) 0.0431(5) -0.0038(4) -0.0013(4) -0.0170(4) C9A 0.0504(6) 0.0484(5) 0.0444(5) -0.0016(4) -0.0042(4) -0.0196(4) C10 0.0477(5) 0.0550(6) 0.0484(6) -0.0040(4) 0.0028(4) -0.0206(5) C10A 0.0524(6) 0.0514(6) 0.0447(5) -0.0010(4) -0.0039(4) -0.0256(5) C11 0.055(2) 0.0437(17) 0.0434(19) -0.0008(11) 0.0105(16) -0.0037(17) O1 0.101(3) 0.079(3) 0.0599(13) -0.0240(16) 0.0155(16) -0.0261(15) O2 0.0547(14) 0.1112(19) 0.0609(17) 0.0048(15) 0.0083(11) -0.0217(12) C12 0.059(2) 0.108(3) 0.075(2) 0.022(2) 0.0108(15) -0.0065(17) C13 0.0726(18) 0.0799(17) 0.0726(18) -0.0038(13) 0.0032(14) -0.0342(14) C14 0.083(3) 0.123(4) 0.082(3) -0.012(2) 0.022(2) -0.057(3) C11D 0.062(3) 0.068(4) 0.059(3) 0.010(2) -0.015(2) -0.032(3) O1D 0.072(2) 0.074(4) 0.081(3) -0.034(3) 0.0145(19) -0.032(2) O2D 0.063(2) 0.116(4) 0.075(3) -0.041(3) 0.021(2) -0.047(3) C12D 0.058(3) 0.119(4) 0.077(3) -0.041(3) 0.022(2) -0.045(3) C13D 0.066(2) 0.104(3) 0.078(3) -0.007(2) 0.006(2) -0.043(2) C14D 0.061(3) 0.130(6) 0.108(5) -0.033(5) 0.019(3) -0.043(3) _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 C2 1.3575(17) . ? C1 C9A 1.4265(15) . ? C1 H1 0.9300 . ? C2 C3 1.4124(18) . ? C2 H2 0.9300 . ? C3 C4 1.3542(17) . ? C3 H3 0.9300 . ? C4 C4A 1.4252(15) . ? C4 H4 0.9300 . ? C4A C10 1.3927(15) . ? C4A C9A 1.4318(15) . ? C5 C6 1.3539(18) . ? C5 C10A 1.4285(15) . ? C5 H5 0.9300 . ? C6 C7 1.411(2) . ? C6 H6 0.9300 . ? C7 C8 1.3525(17) . ? C7 H7 0.9300 . ? C8 C8A 1.4292(15) . ? C8 H8 0.9300 . ? C8A C9 1.4060(15) . ? C8A C10A 1.4303(15) . ? C9 C9A 1.4032(15) . ? C9 C11D 1.488(6) . ? C9 C11 1.520(3) . ? C10 C10A 1.3936(16) . ? C10 H10 0.9300 . ? C11 O1 1.178(5) . ? C11 O2 1.357(5) . ? O2 C12 1.467(4) . ? C12 C13 1.457(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.523(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C11D O1D 1.173(6) . ? C11D O2D 1.340(6) . ? O2D C12D 1.460(5) . ? C12D C13D 1.457(5) . ? C12D H12C 0.9700 . ? C12D H12D 0.9700 . ? C13D C14D 1.517(6) . ? C13D H13C 0.9700 . ? C13D H13D 0.9700 . ? C14D H14D 0.9600 . ? C14D H14E 0.9600 . ? C14D H14F 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 C2 C1 C9A 121.02(11) . . ? C2 C1 H1 119.5 . . ? C9A C1 H1 119.5 . . ? C1 C2 C3 120.78(11) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.17(11) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C4A 121.19(11) . . ? C3 C4 H4 119.4 . . ? C4A C4 H4 119.4 . . ? C10 C4A C4 121.97(10) . . ? C10 C4A C9A 119.35(10) . . ? C4 C4A C9A 118.67(10) . . ? C6 C5 C10A 121.01(11) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 120.30(11) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.89(11) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 121.04(11) . . ? C7 C8 H8 119.5 . . ? C8A C8 H8 119.5 . . ? C9 C8A C8 123.00(10) . . ? C9 C8A C10A 118.93(9) . . ? C8 C8A C10A 118.07(10) . . ? C9A C9 C8A 121.54(9) . . ? C9A C9 C11D 119.4(6) . . ? C8A C9 C11D 118.5(6) . . ? C9A C9 C11 118.7(3) . . ? C8A C9 C11 119.7(3) . . ? C11D C9 C11 10.0(5) . . ? C9 C9A C1 123.00(10) . . ? C9 C9A C4A 118.90(10) . . ? C1 C9A C4A 118.08(10) . . ? C4A C10 C10A 121.93(10) . . ? C4A C10 H10 119.0 . . ? C10A C10 H10 119.0 . . ? C10 C10A C5 122.01(10) . . ? C10 C10A C8A 119.32(10) . . ? C5 C10A C8A 118.67(10) . . ? O1 C11 O2 122.6(4) . . ? O1 C11 C9 124.8(5) . . ? O2 C11 C9 112.5(3) . . ? C11 O2 C12 117.8(3) . . ? C13 C12 O2 111.1(3) . . ? C13 C12 H12A 109.4 . . ? O2 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? O2 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 110.6(4) . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O1D C11D O2D 124.6(6) . . ? O1D C11D C9 127.3(7) . . ? O2D C11D C9 107.5(5) . . ? C11D O2D C12D 115.0(5) . . ? C13D C12D O2D 109.2(4) . . ? C13D C12D H12C 109.8 . . ? O2D C12D H12C 109.8 . . ? C13D C12D H12D 109.8 . . ? O2D C12D H12D 109.8 . . ? H12C C12D H12D 108.3 . . ? C12D C13D C14D 111.6(5) . . ? C12D C13D H13C 109.3 . . ? C14D C13D H13C 109.3 . . ? C12D C13D H13D 109.3 . . ? C14D C13D H13D 109.3 . . ? H13C C13D H13D 108.0 . . ? C13D C14D H14D 109.5 . . ? C13D C14D H14E 109.5 . . ? H14D C14D H14E 109.5 . . ? C13D C14D H14F 109.5 . . ? H14D C14D H14F 109.5 . . ? H14E C14D H14F 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 C9A C1 C2 C3 -0.7(2) . . . . ? C1 C2 C3 C4 2.2(2) . . . . ? C2 C3 C4 C4A -1.0(2) . . . . ? C3 C4 C4A C10 178.70(11) . . . . ? C3 C4 C4A C9A -1.64(18) . . . . ? C10A C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C6 C7 C8 C8A -1.1(2) . . . . ? C7 C8 C8A C9 -178.83(11) . . . . ? C7 C8 C8A C10A 0.73(18) . . . . ? C8 C8A C9 C9A 178.59(10) . . . . ? C10A C8A C9 C9A -0.96(16) . . . . ? C8 C8A C9 C11D 7.1(4) . . . . ? C10A C8A C9 C11D -172.5(4) . . . . ? C8 C8A C9 C11 -4.3(3) . . . . ? C10A C8A C9 C11 176.1(3) . . . . ? C8A C9 C9A C1 178.42(10) . . . . ? C11D C9 C9A C1 -10.1(4) . . . . ? C11 C9 C9A C1 1.3(3) . . . . ? C8A C9 C9A C4A -0.18(17) . . . . ? C11D C9 C9A C4A 171.3(4) . . . . ? C11 C9 C9A C4A -177.3(3) . . . . ? C2 C1 C9A C9 179.46(11) . . . . ? C2 C1 C9A C4A -1.93(18) . . . . ? C10 C4A C9A C9 1.38(16) . . . . ? C4 C4A C9A C9 -178.29(10) . . . . ? C10 C4A C9A C1 -177.29(10) . . . . ? C4 C4A C9A C1 3.04(16) . . . . ? C4 C4A C10 C10A 178.20(10) . . . . ? C9A C4A C10 C10A -1.46(17) . . . . ? C4A C10 C10A C5 -178.76(10) . . . . ? C4A C10 C10A C8A 0.31(17) . . . . ? C6 C5 C10A C10 177.82(11) . . . . ? C6 C5 C10A C8A -1.26(18) . . . . ? C9 C8A C10A C10 0.90(16) . . . . ? C8 C8A C10A C10 -178.67(10) . . . . ? C9 C8A C10A C5 -179.99(10) . . . . ? C8 C8A C10A C5 0.44(16) . . . . ? C9A C9 C11 O1 -74.9(9) . . . . ? C8A C9 C11 O1 108.0(8) . . . . ? C11D C9 C11 O1 22(4) . . . . ? C9A C9 C11 O2 108.9(6) . . . . ? C8A C9 C11 O2 -68.3(6) . . . . ? C11D C9 C11 O2 -154(6) . . . . ? O1 C11 O2 C12 3.9(11) . . . . ? C9 C11 O2 C12 -179.8(4) . . . . ? C11 O2 C12 C13 91.9(8) . . . . ? O2 C12 C13 C14 -180.0(4) . . . . ? C9A C9 C11D O1D -79.4(16) . . . . ? C8A C9 C11D O1D 92.3(15) . . . . ? C11 C9 C11D O1D -168(6) . . . . ? C9A C9 C11D O2D 92.1(9) . . . . ? C8A C9 C11D O2D -96.2(10) . . . . ? C11 C9 C11D O2D 4(4) . . . . ? O1D C11D O2D C12D -6.1(19) . . . . ? C9 C11D O2D C12D -177.9(6) . . . . ? C11D O2D C12D C13D -173.2(11) . . . . ? O2D C12D C13D C14D -173.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.228 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.032 # Attachment 'cb26_0m_C5.cif' data_cb26_0m _database_code_depnum_ccdc_archive 'CCDC 808574' #TrackingRef 'cb26_0m_C5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 O2' _chemical_formula_weight 292.36 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 8.6243(7) _cell_length_b 9.3234(8) _cell_length_c 10.7823(9) _cell_angle_alpha 113.3094(12) _cell_angle_beta 101.2927(12) _cell_angle_gamma 93.6011(13) _cell_volume 771.27(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4852 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 31.06 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-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 16933 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4295 _reflns_number_gt 3205 _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^)+(0.0617P)^2^+0.2770P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4295 _refine_ls_number_parameters 229 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 -0.18773(14) 0.34004(14) 0.42191(12) 0.0196(2) Uani 1 1 d . . . H1 H -0.1350 0.3908 0.3773 0.023 Uiso 1 1 calc R . . C2 C -0.27450(15) 0.42223(15) 0.51235(13) 0.0238(3) Uani 1 1 d . . . H2 H -0.2817 0.5294 0.5296 0.029 Uiso 1 1 calc R . . C3 C -0.35438(15) 0.34918(16) 0.58115(13) 0.0249(3) Uani 1 1 d . . . H3 H -0.4160 0.4072 0.6425 0.030 Uiso 1 1 calc R . . C4 C -0.34275(14) 0.19694(15) 0.55926(13) 0.0225(3) Uani 1 1 d . . . H4 H -0.3947 0.1501 0.6071 0.027 Uiso 1 1 calc R . . C4A C -0.25353(13) 0.10596(14) 0.46531(12) 0.0182(2) Uani 1 1 d . . . C5 C -0.15061(15) -0.30396(15) 0.32021(13) 0.0234(3) Uani 1 1 d . . . H5 H -0.2047 -0.3519 0.3662 0.028 Uiso 1 1 calc R . . C6 C -0.06912(16) -0.39123(15) 0.22823(14) 0.0254(3) Uani 1 1 d . . . H6 H -0.0679 -0.4996 0.2093 0.031 Uiso 1 1 calc R . . C7 C 0.01424(15) -0.32038(14) 0.16031(13) 0.0232(3) Uani 1 1 d . . . H7 H 0.0728 -0.3817 0.0976 0.028 Uiso 1 1 calc R . . C8 C 0.01154(14) -0.16592(14) 0.18361(12) 0.0193(2) Uani 1 1 d . . . H8 H 0.0674 -0.1213 0.1364 0.023 Uiso 1 1 calc R . . C8A C -0.07446(13) -0.06994(13) 0.27848(11) 0.0166(2) Uani 1 1 d . . . C9 C -0.08666(13) 0.08817(13) 0.30191(11) 0.0159(2) Uani 1 1 d . . . C9A C -0.17535(13) 0.17816(13) 0.39358(12) 0.0168(2) Uani 1 1 d . . . C10 C -0.24143(14) -0.05083(14) 0.44191(12) 0.0197(2) Uani 1 1 d . . . H10 H -0.2925 -0.0973 0.4905 0.024 Uiso 1 1 calc R . . C10A C -0.15635(13) -0.14113(14) 0.34905(12) 0.0183(2) Uani 1 1 d . . . C11 C -0.01246(13) 0.15853(13) 0.22021(12) 0.0167(2) Uani 1 1 d . . . O1 O -0.08698(10) 0.19716(11) 0.13439(9) 0.0244(2) Uani 1 1 d . . . O2 O 0.14785(9) 0.17131(10) 0.25137(9) 0.01982(19) Uani 1 1 d . . . C12 C 0.22834(14) 0.22187(16) 0.16492(13) 0.0231(3) Uani 1 1 d . A . H12A H 0.2272 0.3360 0.1899 0.028 Uiso 1 1 calc R . . H12B H 0.1733 0.1622 0.0655 0.028 Uiso 1 1 calc R . . C13 C 0.39838(15) 0.18991(19) 0.19072(15) 0.0288(3) Uani 1 1 d D . . H13A H 0.3983 0.0743 0.1495 0.035 Uiso 0.766(4) 1 calc PR A 1 H13B H 0.4438 0.2306 0.2922 0.035 Uiso 0.766(4) 1 calc PR A 1 H13C H 0.3990 0.0924 0.2067 0.035 Uiso 0.234(4) 1 d PR A 2 H13D H 0.4627 0.2782 0.2765 0.035 Uiso 0.234(4) 1 d PR A 2 C14 C 0.50582(19) 0.2681(3) 0.1279(2) 0.0271(5) Uani 0.766(4) 1 d PD A 1 H14A H 0.5207 0.3842 0.1811 0.033 Uiso 0.766(4) 1 calc PR A 1 H14B H 0.6124 0.2347 0.1401 0.033 Uiso 0.766(4) 1 calc PR A 1 C15 C 0.4411(2) 0.2289(3) -0.02567(19) 0.0252(5) Uani 0.766(4) 1 d PD A 1 H15A H 0.3449 0.2793 -0.0375 0.030 Uiso 0.766(4) 1 calc PR A 1 H15B H 0.4096 0.1131 -0.0786 0.030 Uiso 0.766(4) 1 calc PR A 1 C16 C 0.5697(8) 0.2887(8) -0.0825(5) 0.0391(16) Uani 0.766(4) 1 d PDU A 1 H16A H 0.5238 0.2719 -0.1787 0.059 Uiso 0.766(4) 1 calc PR A 1 H16B H 0.6601 0.2305 -0.0798 0.059 Uiso 0.766(4) 1 calc PR A 1 H16C H 0.6069 0.4018 -0.0252 0.059 Uiso 0.766(4) 1 calc PR A 1 C14D C 0.4768(7) 0.1696(8) 0.0716(6) 0.0246(15) Uani 0.234(4) 1 d PD A 2 H14C H 0.5864 0.1457 0.0938 0.030 Uiso 0.234(4) 1 calc PR A 2 H14D H 0.4147 0.0797 -0.0141 0.030 Uiso 0.234(4) 1 calc PR A 2 C15D C 0.4842(7) 0.3185(8) 0.0475(7) 0.0289(16) Uani 0.234(4) 1 d PD A 2 H15C H 0.5523 0.4070 0.1310 0.035 Uiso 0.234(4) 1 calc PR A 2 H15D H 0.3754 0.3463 0.0312 0.035 Uiso 0.234(4) 1 calc PR A 2 C16D C 0.554(2) 0.2932(18) -0.0807(15) 0.029(4) Uani 0.234(4) 1 d PDU A 2 H16D H 0.5653 0.3922 -0.0921 0.044 Uiso 0.234(4) 1 calc PR A 2 H16E H 0.4825 0.2110 -0.1644 0.044 Uiso 0.234(4) 1 calc PR A 2 H16F H 0.6598 0.2603 -0.0663 0.044 Uiso 0.234(4) 1 calc PR A 2 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 0.0179(5) 0.0227(6) 0.0199(5) 0.0098(4) 0.0060(4) 0.0044(4) C2 0.0239(6) 0.0248(6) 0.0243(6) 0.0099(5) 0.0083(5) 0.0092(5) C3 0.0215(6) 0.0321(7) 0.0231(6) 0.0101(5) 0.0111(5) 0.0093(5) C4 0.0172(5) 0.0323(7) 0.0208(6) 0.0121(5) 0.0085(4) 0.0042(5) C4A 0.0134(5) 0.0246(6) 0.0174(5) 0.0094(4) 0.0044(4) 0.0021(4) C5 0.0233(6) 0.0229(6) 0.0263(6) 0.0138(5) 0.0042(5) 0.0008(5) C6 0.0276(6) 0.0198(6) 0.0285(6) 0.0108(5) 0.0041(5) 0.0039(5) C7 0.0230(6) 0.0215(6) 0.0230(6) 0.0071(5) 0.0049(5) 0.0053(5) C8 0.0174(5) 0.0222(6) 0.0181(5) 0.0082(4) 0.0043(4) 0.0034(4) C8A 0.0142(5) 0.0190(5) 0.0162(5) 0.0076(4) 0.0027(4) 0.0023(4) C9 0.0127(5) 0.0195(5) 0.0162(5) 0.0084(4) 0.0031(4) 0.0018(4) C9A 0.0128(5) 0.0213(5) 0.0175(5) 0.0091(4) 0.0039(4) 0.0031(4) C10 0.0156(5) 0.0256(6) 0.0203(5) 0.0124(5) 0.0044(4) 0.0002(4) C10A 0.0157(5) 0.0216(5) 0.0180(5) 0.0100(4) 0.0021(4) 0.0009(4) C11 0.0144(5) 0.0188(5) 0.0174(5) 0.0068(4) 0.0062(4) 0.0041(4) O1 0.0179(4) 0.0387(5) 0.0274(5) 0.0221(4) 0.0090(3) 0.0105(4) O2 0.0133(4) 0.0289(4) 0.0204(4) 0.0132(3) 0.0052(3) 0.0020(3) C12 0.0151(5) 0.0386(7) 0.0222(6) 0.0174(5) 0.0084(4) 0.0050(5) C13 0.0156(6) 0.0491(8) 0.0313(7) 0.0243(6) 0.0089(5) 0.0088(5) C14 0.0132(7) 0.0469(14) 0.0254(9) 0.0181(9) 0.0073(6) 0.0052(8) C15 0.0158(8) 0.0383(11) 0.0213(9) 0.0104(9) 0.0077(7) 0.0052(7) C16 0.024(2) 0.075(3) 0.036(2) 0.034(2) 0.0203(17) 0.0136(17) C14D 0.016(2) 0.031(4) 0.027(3) 0.008(3) 0.011(2) 0.009(2) C15D 0.021(3) 0.047(4) 0.026(3) 0.019(3) 0.012(2) 0.010(3) C16D 0.015(5) 0.024(5) 0.043(8) 0.008(5) 0.008(4) 0.005(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 C2 1.3655(16) . ? C1 C9A 1.4321(16) . ? C1 H1 0.9500 . ? C2 C3 1.4247(18) . ? C2 H2 0.9500 . ? C3 C4 1.3574(18) . ? C3 H3 0.9500 . ? C4 C4A 1.4301(16) . ? C4 H4 0.9500 . ? C4A C10 1.3961(17) . ? C4A C9A 1.4371(15) . ? C5 C6 1.3586(18) . ? C5 C10A 1.4303(17) . ? C5 H5 0.9500 . ? C6 C7 1.4209(18) . ? C6 H6 0.9500 . ? C7 C8 1.3630(17) . ? C7 H7 0.9500 . ? C8 C8A 1.4329(16) . ? C8 H8 0.9500 . ? C8A C9 1.4083(15) . ? C8A C10A 1.4387(15) . ? C9 C9A 1.4094(15) . ? C9 C11 1.4970(15) . ? C10 C10A 1.3957(16) . ? C10 H10 0.9500 . ? C11 O1 1.2078(14) . ? C11 O2 1.3432(13) . ? O2 C12 1.4605(14) . ? C12 C13 1.5091(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14D 1.519(5) . ? C13 C14 1.549(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 H13C 0.9900 . ? C13 H13D 0.9900 . ? C14 C15 1.523(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.541(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C14D C15D 1.510(7) . ? C14D H14C 0.9900 . ? C14D H14D 0.9900 . ? C15D C16D 1.556(8) . ? C15D H15C 0.9900 . ? C15D H15D 0.9900 . ? C16D H16D 0.9800 . ? C16D H16E 0.9800 . ? C16D H16F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 120.77(11) . . ? C2 C1 H1 119.6 . . ? C9A C1 H1 119.6 . . ? C1 C2 C3 120.81(12) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.17(11) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C4A 121.06(11) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C10 C4A C4 121.40(10) . . ? C10 C4A C9A 119.64(10) . . ? C4 C4A C9A 118.96(11) . . ? C6 C5 C10A 121.13(11) . . ? C6 C5 H5 119.4 . . ? C10A C5 H5 119.4 . . ? C5 C6 C7 120.01(11) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 121.07(11) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C8A 120.81(11) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C9 C8A C8 123.09(10) . . ? C9 C8A C10A 118.85(10) . . ? C8 C8A C10A 118.02(10) . . ? C8A C9 C9A 121.64(10) . . ? C8A C9 C11 118.96(10) . . ? C9A C9 C11 119.28(10) . . ? C9 C9A C1 123.12(10) . . ? C9 C9A C4A 118.66(10) . . ? C1 C9A C4A 118.20(10) . . ? C10A C10 C4A 121.79(10) . . ? C10A C10 H10 119.1 . . ? C4A C10 H10 119.1 . . ? C10 C10A C5 121.66(11) . . ? C10 C10A C8A 119.39(10) . . ? C5 C10A C8A 118.94(10) . . ? O1 C11 O2 123.46(10) . . ? O1 C11 C9 124.45(10) . . ? O2 C11 C9 112.08(9) . . ? C11 O2 C12 115.50(9) . . ? O2 C12 C13 107.31(10) . . ? O2 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? O2 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.5 . . ? C12 C13 C14D 113.7(2) . . ? C12 C13 C14 112.30(12) . . ? C14D C13 C14 32.7(2) . . ? C12 C13 H13A 109.1 . . ? C14D C13 H13A 78.6 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14D C13 H13B 131.5 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C12 C13 H13C 108.8 . . ? C14D C13 H13C 108.5 . . ? C14 C13 H13C 133.0 . . ? H13A C13 H13C 33.4 . . ? H13B C13 H13C 76.9 . . ? C12 C13 H13D 108.8 . . ? C14D C13 H13D 109.1 . . ? C14 C13 H13D 79.7 . . ? H13A C13 H13D 133.4 . . ? H13B C13 H13D 32.9 . . ? H13C C13 H13D 107.7 . . ? C15 C14 C13 114.82(15) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 110.1(3) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C15D C14D C13 110.2(4) . . ? C15D C14D H14C 109.6 . . ? C13 C14D H14C 109.6 . . ? C15D C14D H14D 109.6 . . ? C13 C14D H14D 109.6 . . ? H14C C14D H14D 108.1 . . ? C14D C15D C16D 109.9(8) . . ? C14D C15D H15C 109.7 . . ? C16D C15D H15C 109.7 . . ? C14D C15D H15D 109.7 . . ? C16D C15D H15D 109.7 . . ? H15C C15D H15D 108.2 . . ? C15D C16D H16D 109.5 . . ? C15D C16D H16E 109.5 . . ? H16D C16D H16E 109.5 . . ? C15D C16D H16F 109.5 . . ? H16D C16D H16F 109.5 . . ? H16E C16D H16F 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 C9A C1 C2 C3 0.23(19) . . . . ? C1 C2 C3 C4 1.15(19) . . . . ? C2 C3 C4 C4A -1.27(19) . . . . ? C3 C4 C4A C10 -179.79(11) . . . . ? C3 C4 C4A C9A 0.05(18) . . . . ? C10A C5 C6 C7 0.91(19) . . . . ? C5 C6 C7 C8 -1.33(19) . . . . ? C6 C7 C8 C8A 0.58(18) . . . . ? C7 C8 C8A C9 -177.26(11) . . . . ? C7 C8 C8A C10A 0.55(17) . . . . ? C8 C8A C9 C9A 178.50(10) . . . . ? C10A C8A C9 C9A 0.70(16) . . . . ? C8 C8A C9 C11 2.58(16) . . . . ? C10A C8A C9 C11 -175.22(10) . . . . ? C8A C9 C9A C1 178.75(10) . . . . ? C11 C9 C9A C1 -5.35(16) . . . . ? C8A C9 C9A C4A 0.58(16) . . . . ? C11 C9 C9A C4A 176.49(10) . . . . ? C2 C1 C9A C9 -179.60(11) . . . . ? C2 C1 C9A C4A -1.42(17) . . . . ? C10 C4A C9A C9 -0.61(16) . . . . ? C4 C4A C9A C9 179.54(10) . . . . ? C10 C4A C9A C1 -178.87(10) . . . . ? C4 C4A C9A C1 1.28(16) . . . . ? C4 C4A C10 C10A 179.16(11) . . . . ? C9A C4A C10 C10A -0.68(17) . . . . ? C4A C10 C10A C5 -176.92(11) . . . . ? C4A C10 C10A C8A 1.98(17) . . . . ? C6 C5 C10A C10 179.13(12) . . . . ? C6 C5 C10A C8A 0.22(18) . . . . ? C9 C8A C10A C10 -1.97(16) . . . . ? C8 C8A C10A C10 -179.88(10) . . . . ? C9 C8A C10A C5 176.96(10) . . . . ? C8 C8A C10A C5 -0.95(16) . . . . ? C8A C9 C11 O1 112.88(13) . . . . ? C9A C9 C11 O1 -63.13(16) . . . . ? C8A C9 C11 O2 -65.91(13) . . . . ? C9A C9 C11 O2 118.07(11) . . . . ? O1 C11 O2 C12 -5.56(16) . . . . ? C9 C11 O2 C12 173.25(10) . . . . ? C11 O2 C12 C13 -166.07(10) . . . . ? O2 C12 C13 C14D 155.8(3) . . . . ? O2 C12 C13 C14 -168.69(13) . . . . ? C12 C13 C14 C15 -53.0(2) . . . . ? C14D C13 C14 C15 46.6(4) . . . . ? C13 C14 C15 C16 -170.3(3) . . . . ? C12 C13 C14D C15D 61.0(5) . . . . ? C14 C13 C14D C15D -33.7(4) . . . . ? C13 C14D C15D C16D -176.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.411 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.048 # Attachment 'cb9r_0m.cif' data_cb9r_0m _database_code_depnum_ccdc_archive 'CCDC 808575' #TrackingRef 'cb9r_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H36 O4' _chemical_formula_weight 556.67 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 9.1605(2) _cell_length_b 9.6923(2) _cell_length_c 10.2180(3) _cell_angle_alpha 67.1901(3) _cell_angle_beta 85.3952(4) _cell_angle_gamma 62.2311(3) _cell_volume 734.34(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8529 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 31.77 _exptl_crystal_description 'prism frag' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9710 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17538 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 30.50 _reflns_number_total 4448 _reflns_number_gt 3937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0604P)^2^+0.2229P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4448 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 -0.03414(12) 0.75299(12) 0.37254(10) 0.01787(18) Uani 1 1 d . . . H1 H 0.0677 0.6649 0.3651 0.021 Uiso 1 1 calc R . . C2 C -0.18106(13) 0.74409(14) 0.36850(12) 0.0230(2) Uani 1 1 d . . . H2 H -0.1785 0.6489 0.3599 0.028 Uiso 1 1 calc R . . C3 C -0.33068(13) 0.87304(14) 0.37687(12) 0.0231(2) Uani 1 1 d . . . H3 H -0.4311 0.8684 0.3705 0.028 Uiso 1 1 calc R . . C4 C -0.33349(11) 1.00933(13) 0.39463(10) 0.01828(18) Uani 1 1 d . . . H4 H -0.4360 1.0978 0.4008 0.022 Uiso 1 1 calc R . . C4A C -0.18641(11) 1.01650(11) 0.40345(9) 0.01368(16) Uani 1 1 d . . . C5 C -0.11815(12) 1.38750(12) 0.26951(10) 0.01802(18) Uani 1 1 d . . . H5 H -0.2222 1.4697 0.2807 0.022 Uiso 1 1 calc R . . C6 C -0.01121(13) 1.43956(13) 0.18638(11) 0.0225(2) Uani 1 1 d . . . H6 H -0.0413 1.5568 0.1418 0.027 Uiso 1 1 calc R . . C7 C 0.13995(13) 1.31897(13) 0.16889(11) 0.0221(2) Uani 1 1 d . . . H7 H 0.2139 1.3539 0.1128 0.026 Uiso 1 1 calc R . . C8 C 0.18362(12) 1.14716(12) 0.23311(10) 0.01743(18) Uani 1 1 d . . . H8 H 0.2865 1.0655 0.2196 0.021 Uiso 1 1 calc R . . C8A C 0.07702(11) 1.09443(11) 0.31717(9) 0.01346(16) Uani 1 1 d . . . C9 C 0.11959(10) 0.90777(11) 0.39903(9) 0.01240(16) Uani 1 1 d . . . C9A C -0.03624(10) 0.89072(11) 0.38749(9) 0.01331(16) Uani 1 1 d . . . C10 C -0.18238(10) 1.15478(11) 0.43457(9) 0.01307(16) Uani 1 1 d . . . H10 H -0.2978 1.2518 0.4118 0.016 Uiso 1 1 calc R . . C10A C -0.07395(11) 1.21584(11) 0.33642(9) 0.01392(16) Uani 1 1 d . . . C11 C 0.26207(11) 0.80164(11) 0.33262(9) 0.01402(16) Uani 1 1 d . . . O1 O 0.40446(8) 0.71135(9) 0.38794(8) 0.01980(15) Uani 1 1 d . . . O2 O 0.20667(8) 0.83011(9) 0.20290(7) 0.01641(14) Uani 1 1 d . . . C12 C 0.31764(12) 0.74171(13) 0.11568(10) 0.01981(19) Uani 1 1 d . . . C13 C 0.44746(14) 0.80182(16) 0.07074(13) 0.0292(2) Uani 1 1 d . . . H13A H 0.3918 0.9259 0.0211 0.044 Uiso 1 1 calc R . . H13B H 0.5150 0.7508 0.0064 0.044 Uiso 1 1 calc R . . H13C H 0.5192 0.7675 0.1557 0.044 Uiso 1 1 calc R . . C14 C 0.39340(14) 0.55036(14) 0.19808(12) 0.0257(2) Uani 1 1 d . . . H14A H 0.4650 0.5154 0.2834 0.039 Uiso 1 1 calc R . . H14B H 0.4596 0.4929 0.1370 0.039 Uiso 1 1 calc R . . H14C H 0.3045 0.5195 0.2269 0.039 Uiso 1 1 calc R . . C15 C 0.19821(14) 0.80096(17) -0.01263(12) 0.0308(3) Uani 1 1 d . . . H15A H 0.1106 0.7690 0.0198 0.046 Uiso 1 1 calc R . . H15B H 0.2588 0.7474 -0.0778 0.046 Uiso 1 1 calc R . . H15C H 0.1482 0.9247 -0.0627 0.046 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 C1 0.0190(4) 0.0202(4) 0.0196(4) -0.0110(4) 0.0047(3) -0.0110(3) C2 0.0263(5) 0.0292(5) 0.0280(5) -0.0183(4) 0.0080(4) -0.0194(4) C3 0.0203(4) 0.0349(5) 0.0273(5) -0.0185(4) 0.0066(4) -0.0188(4) C4 0.0140(4) 0.0257(5) 0.0197(4) -0.0123(4) 0.0034(3) -0.0105(4) C4A 0.0139(4) 0.0171(4) 0.0120(4) -0.0068(3) 0.0014(3) -0.0080(3) C5 0.0212(4) 0.0151(4) 0.0158(4) -0.0056(3) 0.0018(3) -0.0075(3) C6 0.0307(5) 0.0170(4) 0.0194(4) -0.0048(4) 0.0049(4) -0.0131(4) C7 0.0273(5) 0.0226(5) 0.0198(4) -0.0072(4) 0.0084(4) -0.0163(4) C8 0.0181(4) 0.0200(4) 0.0164(4) -0.0078(3) 0.0047(3) -0.0107(3) C8A 0.0148(4) 0.0145(4) 0.0120(4) -0.0052(3) 0.0011(3) -0.0075(3) C9 0.0120(3) 0.0139(4) 0.0123(4) -0.0061(3) 0.0018(3) -0.0062(3) C9A 0.0136(4) 0.0164(4) 0.0118(4) -0.0061(3) 0.0015(3) -0.0082(3) C10 0.0122(3) 0.0144(4) 0.0122(4) -0.0056(3) 0.0006(3) -0.0056(3) C10A 0.0154(4) 0.0154(4) 0.0112(4) -0.0050(3) 0.0007(3) -0.0075(3) C11 0.0146(4) 0.0154(4) 0.0144(4) -0.0071(3) 0.0031(3) -0.0082(3) O1 0.0131(3) 0.0241(3) 0.0215(3) -0.0118(3) 0.0011(2) -0.0059(3) O2 0.0142(3) 0.0200(3) 0.0143(3) -0.0097(3) 0.0025(2) -0.0053(2) C12 0.0172(4) 0.0247(5) 0.0177(4) -0.0135(4) 0.0051(3) -0.0064(4) C13 0.0258(5) 0.0366(6) 0.0286(5) -0.0167(5) 0.0145(4) -0.0161(5) C14 0.0246(5) 0.0232(5) 0.0298(5) -0.0167(4) 0.0034(4) -0.0068(4) C15 0.0255(5) 0.0412(6) 0.0211(5) -0.0199(5) 0.0003(4) -0.0057(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 C9A 1.3927(12) . ? C1 C2 1.3930(13) . ? C1 H1 0.9500 . ? C2 C3 1.3841(15) . ? C2 H2 0.9500 . ? C3 C4 1.3900(14) . ? C3 H3 0.9500 . ? C4 C4A 1.3928(12) . ? C4 H4 0.9500 . ? C4A C9A 1.4002(12) . ? C4A C10 1.5090(12) . ? C5 C6 1.3894(14) . ? C5 C10A 1.3908(12) . ? C5 H5 0.9500 . ? C6 C7 1.3892(15) . ? C6 H6 0.9500 . ? C7 C8 1.3921(13) . ? C7 H7 0.9500 . ? C8 C8A 1.3937(12) . ? C8 H8 0.9500 . ? C8A C10A 1.3983(12) . ? C8A C9 1.5318(12) . ? C9 C9A 1.5300(12) . ? C9 C11 1.5395(12) . ? C9 C10 1.6192(12) 2_576 ? C10 C10A 1.5068(12) . ? C10 C9 1.6192(12) 2_576 ? C10 H10 1.0000 . ? C11 O1 1.2074(11) . ? C11 O2 1.3358(11) . ? O2 C12 1.4821(11) . ? C12 C15 1.5188(14) . ? C12 C14 1.5212(15) . ? C12 C13 1.5215(15) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C9A C1 C2 120.16(9) . . ? C9A C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.45(9) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.75(9) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C4A 120.15(9) . . ? C3 C4 H4 119.9 . . ? C4A C4 H4 119.9 . . ? C4 C4A C9A 120.12(8) . . ? C4 C4A C10 121.69(8) . . ? C9A C4A C10 118.17(7) . . ? C6 C5 C10A 120.48(9) . . ? C6 C5 H5 119.8 . . ? C10A C5 H5 119.8 . . ? C7 C6 C5 119.55(9) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.31(9) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C8A 120.27(9) . . ? C7 C8 H8 119.9 . . ? C8A C8 H8 119.9 . . ? C8 C8A C10A 119.31(8) . . ? C8 C8A C9 123.73(8) . . ? C10A C8A C9 116.85(7) . . ? C9A C9 C8A 108.57(7) . . ? C9A C9 C11 111.77(7) . . ? C8A C9 C11 107.88(7) . . ? C9A C9 C10 109.91(7) . 2_576 ? C8A C9 C10 110.07(7) . 2_576 ? C11 C9 C10 108.61(7) . 2_576 ? C1 C9A C4A 119.22(8) . . ? C1 C9A C9 123.81(8) . . ? C4A C9A C9 116.81(7) . . ? C10A C10 C4A 108.34(7) . . ? C10A C10 C9 111.64(7) . 2_576 ? C4A C10 C9 112.28(7) . 2_576 ? C10A C10 H10 108.1 . . ? C4A C10 H10 108.1 . . ? C9 C10 H10 108.1 2_576 . ? C5 C10A C8A 120.05(8) . . ? C5 C10A C10 121.69(8) . . ? C8A C10A C10 118.23(7) . . ? O1 C11 O2 125.20(8) . . ? O1 C11 C9 124.57(8) . . ? O2 C11 C9 110.17(7) . . ? C11 O2 C12 121.53(7) . . ? O2 C12 C15 102.35(7) . . ? O2 C12 C14 109.94(8) . . ? C15 C12 C14 110.63(9) . . ? O2 C12 C13 109.39(8) . . ? C15 C12 C13 110.96(9) . . ? C14 C12 C13 113.04(9) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C9A C1 C2 C3 1.08(16) . . . . ? C1 C2 C3 C4 -2.34(16) . . . . ? C2 C3 C4 C4A 0.24(15) . . . . ? C3 C4 C4A C9A 3.11(14) . . . . ? C3 C4 C4A C10 -174.99(9) . . . . ? C10A C5 C6 C7 0.77(15) . . . . ? C5 C6 C7 C8 0.55(15) . . . . ? C6 C7 C8 C8A -0.88(15) . . . . ? C7 C8 C8A C10A -0.10(14) . . . . ? C7 C8 C8A C9 -176.15(8) . . . . ? C8 C8A C9 C9A -140.34(8) . . . . ? C10A C8A C9 C9A 43.52(10) . . . . ? C8 C8A C9 C11 -19.05(11) . . . . ? C10A C8A C9 C11 164.82(7) . . . . ? C8 C8A C9 C10 99.30(9) . . . 2_576 ? C10A C8A C9 C10 -76.83(9) . . . 2_576 ? C2 C1 C9A C4A 2.24(14) . . . . ? C2 C1 C9A C9 177.43(9) . . . . ? C4 C4A C9A C1 -4.33(13) . . . . ? C10 C4A C9A C1 173.84(8) . . . . ? C4 C4A C9A C9 -179.85(8) . . . . ? C10 C4A C9A C9 -1.68(11) . . . . ? C8A C9 C9A C1 142.26(9) . . . . ? C11 C9 C9A C1 23.38(12) . . . . ? C10 C9 C9A C1 -97.29(10) 2_576 . . . ? C8A C9 C9A C4A -42.45(10) . . . . ? C11 C9 C9A C4A -161.33(7) . . . . ? C10 C9 C9A C4A 78.00(9) 2_576 . . . ? C4 C4A C10 C10A -136.93(9) . . . . ? C9A C4A C10 C10A 44.93(10) . . . . ? C4 C4A C10 C9 99.32(10) . . . 2_576 ? C9A C4A C10 C9 -78.82(10) . . . 2_576 ? C6 C5 C10A C8A -1.76(14) . . . . ? C6 C5 C10A C10 176.12(8) . . . . ? C8 C8A C10A C5 1.41(13) . . . . ? C9 C8A C10A C5 177.73(8) . . . . ? C8 C8A C10A C10 -176.54(8) . . . . ? C9 C8A C10A C10 -0.22(11) . . . . ? C4A C10 C10A C5 138.21(8) . . . . ? C9 C10 C10A C5 -97.65(9) 2_576 . . . ? C4A C10 C10A C8A -43.88(10) . . . . ? C9 C10 C10A C8A 80.26(9) 2_576 . . . ? C9A C9 C11 O1 -134.32(9) . . . . ? C8A C9 C11 O1 106.39(10) . . . . ? C10 C9 C11 O1 -12.89(12) 2_576 . . . ? C9A C9 C11 O2 48.48(9) . . . . ? C8A C9 C11 O2 -70.80(8) . . . . ? C10 C9 C11 O2 169.91(7) 2_576 . . . ? O1 C11 O2 C12 3.91(14) . . . . ? C9 C11 O2 C12 -178.92(7) . . . . ? C11 O2 C12 C15 174.89(9) . . . . ? C11 O2 C12 C14 57.29(11) . . . . ? C11 O2 C12 C13 -67.39(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.460 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.049