# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fernando Garcia-Tellado' _publ_contact_author_email FGARCIA@IPNA.CSIC.ES _publ_section_title ; Ambiphilic Allenes: Synthesis and Reactivity ; loop_ _publ_author_name 'Fernando Garcia-Tellado' 'Javier Gonzalez-Platas' 'Gabriela Mendez-Abt' 'Miguel A. Ramirez' ; D.Tejedor ; # Attachment 'dt743_rev2.cif' data_dt743 _database_code_depnum_ccdc_archive 'CCDC 704023' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3Z,4Z)-3,4-bis(2-methoxy-2-oxoethylidene)-1,2-diphenylcyclobutane -1,2-diyl dibenzoate ; _chemical_name_common ; (3Z,4Z)-3,4-bis(2-methoxy-2-oxoethylidene)-1,2- diphenylcyclobutane -1,2-diyl dibenzoate ; _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 O8' _chemical_formula_sum 'C36 H28 O8' _chemical_formula_weight 588.58 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 'C 2/c' 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' '-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 31.764(3) _cell_length_b 10.8730(10) _cell_length_c 18.823(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.707(5) _cell_angle_gamma 90.00 _cell_volume 6498.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34744 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.16 _reflns_number_total 5184 _reflns_number_gt 4212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Altomare et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. A solvent molecule of dichloromethane presented a higher disorder. It was impossible to establish a good model for the solvent molecule even using an isotropic refinement. Therefore a SQUEZZE procedure was made in order to eliminate the contribution of the solvemt molecule in the structure. ; _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^)+(0.0812P)^2^+8.7563P] 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 0.0055(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5184 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2019 _refine_ls_wR_factor_gt 0.1913 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 O3 O 0.14953(7) 0.0612(2) 0.41419(11) 0.0438(6) Uani 1 1 d . . . O4 O 0.21099(8) 0.1460(2) 0.38273(12) 0.0501(6) Uani 1 1 d . . . O2 O 0.21219(8) -0.0742(2) 0.50051(14) 0.0589(7) Uani 1 1 d . . . O3' O 0.08952(6) 0.2932(2) 0.49755(11) 0.0422(6) Uani 1 1 d . . . O1 O 0.25785(8) -0.0392(2) 0.59067(13) 0.0551(7) Uani 1 1 d . . . O1' O 0.17867(8) 0.6058(2) 0.58650(15) 0.0633(8) Uani 1 1 d . . . O4' O 0.10857(8) 0.3167(3) 0.61319(13) 0.0578(7) Uani 1 1 d . . . O2' O 0.13065(10) 0.5441(3) 0.50561(18) 0.0760(9) Uani 1 1 d . . . C2 C 0.17021(9) 0.3049(3) 0.51408(16) 0.0355(7) Uani 1 1 d . . . C6 C 0.22868(10) -0.0056(3) 0.54250(18) 0.0397(8) Uani 1 1 d . . . C9' C 0.03753(10) 0.3516(3) 0.57568(18) 0.0424(8) Uani 1 1 d . . . C1 C 0.18571(9) 0.1786(3) 0.51656(16) 0.0325(7) Uani 1 1 d . . . C15' C 0.12695(10) 0.3131(3) 0.39411(17) 0.0433(8) Uani 1 1 d . . . C9 C 0.18543(11) -0.0341(3) 0.32303(17) 0.0438(9) Uani 1 1 d . . . C5 C 0.22022(10) 0.1279(3) 0.54687(16) 0.0362(8) Uani 1 1 d . . . H5 H 0.2394 0.1781 0.5713 0.043 Uiso 1 1 calc R . . C4 C 0.14581(10) 0.1282(3) 0.48043(17) 0.0383(8) Uani 1 1 d . . . C8' C 0.08232(10) 0.3182(3) 0.56577(18) 0.0399(8) Uani 1 1 d . . . C8 C 0.18439(11) 0.0679(3) 0.37519(17) 0.0417(8) Uani 1 1 d . . . C6' C 0.16189(12) 0.5251(3) 0.5415(2) 0.0473(9) Uani 1 1 d . . . C20' C 0.09301(13) 0.2751(4) 0.3517(2) 0.0638(11) Uani 1 1 d . . . H20' H 0.0733 0.2211 0.3697 0.077 Uiso 1 1 calc R . . C3 C 0.13075(9) 0.2691(3) 0.47023(17) 0.0371(8) Uani 1 1 d . . . C5' C 0.18533(10) 0.4085(3) 0.54289(17) 0.0381(8) Uani 1 1 d . . . H5' H 0.2119 0.4070 0.5649 0.046 Uiso 1 1 calc R . . C10 C 0.22203(14) -0.0506(4) 0.2852(2) 0.0610(11) Uani 1 1 d . . . H10 H 0.2448 0.0022 0.2925 0.073 Uiso 1 1 calc R . . C15 C 0.11707(10) 0.0522(3) 0.52489(19) 0.0427(8) Uani 1 1 d . . . C14 C 0.15233(13) -0.1142(4) 0.3121(2) 0.0594(10) Uani 1 1 d . . . H14 H 0.1280 -0.1055 0.3380 0.071 Uiso 1 1 calc R . . C17 C 0.09653(15) -0.0351(4) 0.6358(3) 0.0720(12) Uani 1 1 d . . . H17 H 0.1020 -0.0473 0.6841 0.086 Uiso 1 1 calc R . . C16 C 0.12439(12) 0.0315(3) 0.5966(2) 0.0530(10) Uani 1 1 d . . . H16 H 0.1486 0.0631 0.6188 0.064 Uiso 1 1 calc R . . C11 C 0.22446(16) -0.1454(4) 0.2369(2) 0.0738(13) Uani 1 1 d . . . H11 H 0.2489 -0.1565 0.2118 0.089 Uiso 1 1 calc R . . C18 C 0.06118(17) -0.0830(4) 0.6047(3) 0.0856(15) Uani 1 1 d . . . H18 H 0.0426 -0.1286 0.6314 0.103 Uiso 1 1 calc R . . C16' C 0.15611(13) 0.3917(4) 0.3653(2) 0.0571(10) Uani 1 1 d . . . H16' H 0.1795 0.4163 0.3925 0.069 Uiso 1 1 calc R . . C14' C 0.00676(11) 0.3378(4) 0.5226(2) 0.0578(10) Uani 1 1 d . . . H14' H 0.0139 0.3065 0.4786 0.069 Uiso 1 1 calc R . . C10' C 0.02626(13) 0.4011(5) 0.6398(2) 0.0739(13) Uani 1 1 d . . . H10' H 0.0466 0.4124 0.6758 0.089 Uiso 1 1 calc R . . C7 C 0.27090(14) -0.1673(4) 0.5898(2) 0.0683(12) Uani 1 1 d . . . H7A H 0.2485 -0.2181 0.6065 0.102 Uiso 1 1 calc R . . H7B H 0.2955 -0.1778 0.6202 0.102 Uiso 1 1 calc R . . H7C H 0.2773 -0.1908 0.5422 0.102 Uiso 1 1 calc R . . C18' C 0.1171(2) 0.3994(5) 0.2541(2) 0.0856(15) Uani 1 1 d . . . H18' H 0.1135 0.4295 0.2081 0.103 Uiso 1 1 calc R . . C13' C -0.03422(12) 0.3698(4) 0.5346(3) 0.0715(12) Uani 1 1 d . . . H13' H -0.0547 0.3588 0.4988 0.086 Uiso 1 1 calc R . . C12' C -0.04525(13) 0.4171(5) 0.5980(3) 0.0774(14) Uani 1 1 d . . . H12' H -0.0731 0.4381 0.6055 0.093 Uiso 1 1 calc R . . C19' C 0.08832(17) 0.3176(5) 0.2819(3) 0.0857(16) Uani 1 1 d . . . H19' H 0.0656 0.2908 0.2536 0.103 Uiso 1 1 calc R . . C20 C 0.08072(12) 0.0032(4) 0.4932(2) 0.0660(11) Uani 1 1 d . . . H20 H 0.0749 0.0152 0.4450 0.079 Uiso 1 1 calc R . . C19 C 0.05293(15) -0.0641(4) 0.5341(4) 0.0857(15) Uani 1 1 d . . . H19 H 0.0285 -0.0964 0.5129 0.103 Uiso 1 1 calc R . . C7' C 0.15614(17) 0.7228(4) 0.5910(3) 0.0874(15) Uani 1 1 d . . . H7'1 H 0.1582 0.7664 0.5468 0.131 Uiso 1 1 calc R . . H7'2 H 0.1684 0.7714 0.6288 0.131 Uiso 1 1 calc R . . H7'3 H 0.1271 0.7073 0.6002 0.131 Uiso 1 1 calc R . . C11' C -0.01531(16) 0.4341(6) 0.6508(3) 0.0939(17) Uani 1 1 d . . . H11' H -0.0228 0.4676 0.6941 0.113 Uiso 1 1 calc R . . C13 C 0.15519(16) -0.2080(4) 0.2624(2) 0.0692(12) Uani 1 1 d . . . H13 H 0.1325 -0.2606 0.2540 0.083 Uiso 1 1 calc R . . C12 C 0.19126(18) -0.2232(4) 0.2258(2) 0.0714(13) Uani 1 1 d . . . H12 H 0.1932 -0.2869 0.1931 0.086 Uiso 1 1 calc R . . C17' C 0.15073(17) 0.4344(4) 0.2961(2) 0.0779(13) Uani 1 1 d . . . H17' H 0.1705 0.4880 0.2779 0.093 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 O3 0.0411(13) 0.0440(13) 0.0460(13) -0.0155(10) -0.0037(11) 0.0009(10) O4 0.0538(15) 0.0475(14) 0.0491(14) -0.0085(11) 0.0039(11) -0.0042(13) O2 0.0709(18) 0.0347(14) 0.0700(17) -0.0054(13) -0.0181(14) 0.0058(12) O3' 0.0317(12) 0.0496(14) 0.0454(13) -0.0083(11) 0.0002(10) 0.0059(10) O1 0.0613(16) 0.0405(14) 0.0626(16) 0.0039(11) -0.0138(13) 0.0146(12) O1' 0.0656(17) 0.0350(13) 0.089(2) -0.0203(14) 0.0053(15) 0.0026(12) O4' 0.0428(14) 0.0838(19) 0.0464(14) -0.0010(13) -0.0033(12) 0.0101(13) O2' 0.069(2) 0.0522(17) 0.105(2) -0.0096(15) -0.0251(18) 0.0245(14) C2 0.0344(17) 0.0339(17) 0.0385(17) 0.0006(14) 0.0024(14) 0.0031(14) C6 0.0380(19) 0.0365(19) 0.0447(19) 0.0025(16) 0.0013(16) 0.0046(15) C9' 0.0368(18) 0.0437(19) 0.047(2) -0.0002(16) 0.0039(15) 0.0045(15) C1 0.0300(17) 0.0300(16) 0.0375(17) -0.0054(13) 0.0008(13) 0.0017(13) C15' 0.0410(19) 0.044(2) 0.0448(19) -0.0051(16) -0.0032(16) 0.0136(16) C9 0.055(2) 0.0405(19) 0.0354(18) -0.0045(15) -0.0090(16) 0.0076(17) C5 0.0358(18) 0.0350(18) 0.0380(17) -0.0041(14) 0.0009(14) 0.0003(14) C4 0.0349(17) 0.0377(18) 0.0423(18) -0.0070(15) 0.0002(14) 0.0031(14) C8' 0.0394(19) 0.0366(18) 0.043(2) -0.0031(15) -0.0009(16) 0.0045(15) C8 0.042(2) 0.0401(19) 0.0428(19) -0.0031(15) -0.0027(16) 0.0057(17) C6' 0.046(2) 0.0360(19) 0.060(2) -0.0049(17) 0.0077(19) 0.0016(16) C20' 0.060(3) 0.074(3) 0.056(2) -0.006(2) -0.014(2) 0.002(2) C3 0.0296(17) 0.0389(18) 0.0428(18) -0.0024(14) 0.0007(14) 0.0010(14) C5' 0.0312(17) 0.0363(18) 0.0468(19) -0.0049(15) 0.0004(14) 0.0019(14) C10 0.073(3) 0.062(3) 0.049(2) -0.0073(19) 0.014(2) 0.003(2) C15 0.0376(19) 0.0310(17) 0.060(2) -0.0067(16) 0.0067(16) 0.0025(14) C14 0.061(2) 0.059(2) 0.058(2) -0.017(2) -0.0093(19) 0.010(2) C17 0.075(3) 0.063(3) 0.080(3) 0.005(2) 0.029(3) -0.004(2) C16 0.054(2) 0.046(2) 0.060(2) -0.0065(18) 0.0153(19) -0.0048(17) C11 0.096(3) 0.083(3) 0.044(2) -0.016(2) 0.018(2) 0.009(3) C18 0.072(3) 0.065(3) 0.121(5) 0.017(3) 0.039(3) -0.007(3) C16' 0.058(2) 0.056(2) 0.057(2) 0.0081(19) 0.0013(19) 0.008(2) C14' 0.040(2) 0.067(3) 0.066(2) -0.016(2) 0.0012(18) 0.0044(18) C10' 0.052(2) 0.114(4) 0.055(2) -0.007(2) -0.0012(19) 0.027(2) C7 0.074(3) 0.044(2) 0.086(3) 0.010(2) -0.014(2) 0.020(2) C18' 0.111(4) 0.098(4) 0.048(3) 0.011(3) 0.003(3) 0.033(3) C13' 0.041(2) 0.086(3) 0.087(3) -0.013(3) -0.008(2) 0.011(2) C12' 0.040(2) 0.107(4) 0.085(3) 0.004(3) 0.010(2) 0.022(2) C19' 0.088(4) 0.107(4) 0.060(3) -0.019(3) -0.031(3) 0.032(3) C20 0.051(2) 0.063(3) 0.083(3) -0.002(2) -0.007(2) -0.012(2) C19 0.053(3) 0.062(3) 0.142(5) 0.000(3) 0.005(3) -0.022(2) C7' 0.104(4) 0.037(2) 0.122(4) -0.012(2) 0.032(3) 0.010(2) C11' 0.074(3) 0.143(5) 0.066(3) -0.010(3) 0.020(3) 0.043(3) C13 0.090(3) 0.051(2) 0.066(3) -0.020(2) -0.018(2) 0.000(2) C12 0.117(4) 0.054(3) 0.043(2) -0.0145(19) -0.003(2) 0.016(3) C17' 0.095(4) 0.079(3) 0.060(3) 0.019(2) 0.010(3) 0.018(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 O3 C8 1.349(4) . ? O3 C4 1.452(4) . ? O4 C8 1.203(4) . ? O2 C6 1.196(4) . ? O3' C8' 1.339(4) . ? O3' C3 1.445(4) . ? O1 C6 1.328(4) . ? O1 C7 1.454(4) . ? O1' C6' 1.321(4) . ? O1' C7' 1.463(5) . ? O4' C8' 1.203(4) . ? O2' C6' 1.202(4) . ? C2 C5' 1.334(4) . ? C2 C1 1.460(4) . ? C2 C3 1.531(4) . ? C6 C5 1.479(5) . ? C9' C10' 1.377(5) . ? C9' C14' 1.384(5) . ? C9' C8' 1.486(5) . ? C1 C5 1.339(4) . ? C1 C4 1.522(4) . ? C15' C16' 1.384(5) . ? C15' C20' 1.385(5) . ? C15' C3 1.512(5) . ? C9 C14 1.376(5) . ? C9 C10 1.393(5) . ? C9 C8 1.483(5) . ? C5 H5 0.9300 . ? C4 C15 1.504(5) . ? C4 C3 1.615(4) . ? C6' C5' 1.470(5) . ? C20' C19' 1.397(6) . ? C20' H20' 0.9300 . ? C5' H5' 0.9300 . ? C10 C11 1.377(6) . ? C10 H10 0.9300 . ? C15 C16 1.381(5) . ? C15 C20 1.390(5) . ? C14 C13 1.390(5) . ? C14 H14 0.9300 . ? C17 C18 1.355(7) . ? C17 C16 1.375(6) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C11 C12 1.363(7) . ? C11 H11 0.9300 . ? C18 C19 1.363(7) . ? C18 H18 0.9300 . ? C16' C17' 1.388(6) . ? C16' H16' 0.9300 . ? C14' C13' 1.373(5) . ? C14' H14' 0.9300 . ? C10' C11' 1.390(6) . ? C10' H10' 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C18' C17' 1.364(7) . ? C18' C19' 1.387(8) . ? C18' H18' 0.9300 . ? C13' C12' 1.355(6) . ? C13' H13' 0.9300 . ? C12' C11' 1.368(7) . ? C12' H12' 0.9300 . ? C19' H19' 0.9300 . ? C20 C19 1.395(7) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C7' H7'1 0.9600 . ? C7' H7'2 0.9600 . ? C7' H7'3 0.9600 . ? C11' H11' 0.9300 . ? C13 C12 1.364(7) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C17' H17' 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O3 C4 122.0(2) . . ? C8' O3' C3 124.1(2) . . ? C6 O1 C7 116.7(3) . . ? C6' O1' C7' 115.2(3) . . ? C5' C2 C1 131.7(3) . . ? C5' C2 C3 135.5(3) . . ? C1 C2 C3 92.7(2) . . ? O2 C6 O1 124.2(3) . . ? O2 C6 C5 124.9(3) . . ? O1 C6 C5 110.9(3) . . ? C10' C9' C14' 118.5(3) . . ? C10' C9' C8' 118.7(3) . . ? C14' C9' C8' 122.7(3) . . ? C5 C1 C2 132.2(3) . . ? C5 C1 C4 134.6(3) . . ? C2 C1 C4 92.8(2) . . ? C16' C15' C20' 118.5(3) . . ? C16' C15' C3 122.1(3) . . ? C20' C15' C3 119.4(3) . . ? C14 C9 C10 119.2(3) . . ? C14 C9 C8 122.7(3) . . ? C10 C9 C8 118.1(3) . . ? C1 C5 C6 121.8(3) . . ? C1 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? O3 C4 C15 105.6(2) . . ? O3 C4 C1 118.4(2) . . ? C15 C4 C1 117.4(3) . . ? O3 C4 C3 113.9(2) . . ? C15 C4 C3 113.9(2) . . ? C1 C4 C3 87.2(2) . . ? O4' C8' O3' 125.1(3) . . ? O4' C8' C9' 123.7(3) . . ? O3' C8' C9' 111.2(3) . . ? O4 C8 O3 124.0(3) . . ? O4 C8 C9 125.2(3) . . ? O3 C8 C9 110.8(3) . . ? O2' C6' O1' 123.9(3) . . ? O2' C6' C5' 124.6(3) . . ? O1' C6' C5' 111.6(3) . . ? C15' C20' C19' 120.2(4) . . ? C15' C20' H20' 119.9 . . ? C19' C20' H20' 119.9 . . ? O3' C3 C15' 103.4(2) . . ? O3' C3 C2 119.9(2) . . ? C15' C3 C2 118.1(3) . . ? O3' C3 C4 113.4(2) . . ? C15' C3 C4 115.3(3) . . ? C2 C3 C4 86.7(2) . . ? C2 C5' C6' 123.0(3) . . ? C2 C5' H5' 118.5 . . ? C6' C5' H5' 118.5 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C16 C15 C20 118.0(3) . . ? C16 C15 C4 123.1(3) . . ? C20 C15 C4 118.8(3) . . ? C9 C14 C13 120.0(4) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C18 C17 C16 120.6(5) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C16 C15 121.2(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C17 C18 C19 119.8(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C15' C16' C17' 120.6(4) . . ? C15' C16' H16' 119.7 . . ? C17' C16' H16' 119.7 . . ? C13' C14' C9' 120.4(4) . . ? C13' C14' H14' 119.8 . . ? C9' C14' H14' 119.8 . . ? C9' C10' C11' 120.3(4) . . ? C9' C10' H10' 119.8 . . ? C11' C10' H10' 119.8 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C17' C18' C19' 118.3(4) . . ? C17' C18' H18' 120.9 . . ? C19' C18' H18' 120.9 . . ? C12' C13' C14' 120.8(4) . . ? C12' C13' H13' 119.6 . . ? C14' C13' H13' 119.6 . . ? C13' C12' C11' 119.9(4) . . ? C13' C12' H12' 120.0 . . ? C11' C12' H12' 120.0 . . ? C18' C19' C20' 120.9(5) . . ? C18' C19' H19' 119.6 . . ? C20' C19' H19' 119.6 . . ? C15 C20 C19 119.7(4) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C18 C19 C20 120.7(5) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? O1' C7' H7'1 109.5 . . ? O1' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? O1' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? C12' C11' C10' 119.9(4) . . ? C12' C11' H11' 120.0 . . ? C10' C11' H11' 120.0 . . ? C12 C13 C14 120.1(4) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C18' C17' C16' 121.5(5) . . ? C18' C17' H17' 119.3 . . ? C16' C17' H17' 119.3 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.16 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.332 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.080 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C16' H16' O1 0.9300 2.4100 3.258(6) 151.00 7_556 yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.078 0.250 140 29 ' ' 2 0.000 0.078 0.750 141 29 ' ' 3 0.500 0.200 0.672 7 0 ' ' 4 0.500 0.200 0.828 8 0 ' ' 5 0.500 0.422 0.250 140 29 ' ' 6 0.000 0.306 0.168 7 0 ' ' 7 0.000 0.306 0.332 8 0 ' ' 8 0.500 0.581 0.750 140 29 ' ' 9 0.000 0.694 0.668 7 0 ' ' 10 0.000 0.694 0.832 7 0 ' ' 11 0.500 0.806 0.168 7 0 ' ' 12 0.500 0.806 0.332 8 0 ' ' _platon_squeeze_details ; ; # Attachment 'dt743c_rev2.cif' data_dt743c _database_code_depnum_ccdc_archive 'CCDC 704024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-((E)-4-(2-methoxy-2-oxothylidene)-2-(methoxycarbonyl)-3- phenylcyclobut-2-enylidene)(phenyl)methyl benzoate ; _chemical_name_common ; (E)-((E)-4-(2-methoxy-2-oxothylidene)-2-(methoxycarbonyl)-3- phenylcyclobut-2-enylidene)(phenyl)methyl benzoate ; _chemical_melting_point ? _chemical_formula_moiety 'C29 H22 O6' _chemical_formula_sum 'C29 H22 O6' _chemical_formula_weight 466.47 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 'P 21/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 10.7690(10) _cell_length_b 9.6780(10) _cell_length_c 23.3110(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.400(2) _cell_angle_gamma 90.00 _cell_volume 2414.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27643 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3454 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Altomare et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One carboxilic group present a medium disorder that was modeled in two sites with 30% and 70% of probablity. ; _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^)+(0.0945P)^2^+2.9129P] 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 3454 _refine_ls_number_parameters 335 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1955 _refine_ls_wR_factor_gt 0.1877 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.085 _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 O1 O 0.3840(2) 1.0725(2) 0.20002(9) 0.0389(6) Uani 1 1 d . . . O2 O 0.2904(3) 1.2736(3) 0.21757(12) 0.0698(9) Uani 1 1 d . . . O3A O 0.0791(11) 0.6919(16) 0.2655(7) 0.062(4) Uani 0.297(10) 1 d P A 1 O4A O 0.275(2) 0.640(3) 0.3023(7) 0.0625(17) Uani 0.297(10) 1 d PD A 1 O3B O 0.1091(7) 0.6256(7) 0.2425(3) 0.080(2) Uani 0.703(10) 1 d P A 2 O4B O 0.2566(8) 0.6610(11) 0.3174(3) 0.0625(17) Uani 0.703(10) 1 d PD A 2 O5 O 0.2284(2) 0.9354(3) 0.00934(10) 0.0578(7) Uani 1 1 d . . . O6 O 0.0363(3) 0.8448(3) 0.00422(12) 0.0697(8) Uani 1 1 d . . . C1 C 0.2354(3) 0.9517(3) 0.14067(12) 0.0328(7) Uani 1 1 d . . . C2 C 0.1521(3) 0.8793(3) 0.09532(14) 0.0361(8) Uani 1 1 d . . . C3 C 0.1107(3) 0.7869(3) 0.13312(15) 0.0387(8) Uani 1 1 d . . . C4 C 0.1972(3) 0.8455(3) 0.18197(13) 0.0351(7) Uani 1 1 d . . . C5 C 0.3112(3) 1.0607(3) 0.14580(13) 0.0335(7) Uani 1 1 d . . . C6 C 0.3652(3) 1.1854(4) 0.23279(14) 0.0421(8) Uani 1 1 d . . . C7 C 0.4455(3) 1.1810(3) 0.28868(14) 0.0401(8) Uani 1 1 d . . . C8 C 0.4351(4) 1.2868(4) 0.32811(15) 0.0519(10) Uani 1 1 d . . . H8 H 0.3818 1.3609 0.3187 0.062 Uiso 1 1 calc R . . C9 C 0.5048(4) 1.2808(5) 0.38150(16) 0.0608(11) Uani 1 1 d . . . H9 H 0.4981 1.3512 0.4081 0.073 Uiso 1 1 calc R . . C10 C 0.5833(4) 1.1724(5) 0.39541(16) 0.0610(11) Uani 1 1 d . . . H10 H 0.6293 1.1694 0.4316 0.073 Uiso 1 1 calc R . . C11 C 0.5952(4) 1.0680(5) 0.35675(16) 0.0579(10) Uani 1 1 d . . . H11 H 0.6495 0.9948 0.3665 0.069 Uiso 1 1 calc R . . C12 C 0.5266(3) 1.0719(4) 0.30351(14) 0.0466(9) Uani 1 1 d . . . H12 H 0.5344 1.0011 0.2772 0.056 Uiso 1 1 calc R . . C13 C 0.3370(3) 1.1610(3) 0.10170(13) 0.0337(7) Uani 1 1 d . . . C14 C 0.2406(3) 1.2141(4) 0.06392(14) 0.0438(8) Uani 1 1 d . . . H14 H 0.1585 1.1897 0.0679 0.053 Uiso 1 1 calc R . . C15 C 0.2656(4) 1.3033(4) 0.02038(16) 0.0526(10) Uani 1 1 d . . . H15 H 0.2003 1.3374 -0.0052 0.063 Uiso 1 1 calc R . . C16 C 0.3860(4) 1.3416(4) 0.01466(16) 0.0558(10) Uani 1 1 d . . . H16 H 0.4026 1.4013 -0.0148 0.067 Uiso 1 1 calc R . . C17 C 0.4814(4) 1.2919(4) 0.05244(18) 0.0584(11) Uani 1 1 d . . . H17 H 0.5630 1.3185 0.0486 0.070 Uiso 1 1 calc R . . C18 C 0.4586(3) 1.2030(4) 0.09615(15) 0.0457(9) Uani 1 1 d . . . H18 H 0.5244 1.1711 0.1220 0.055 Uiso 1 1 calc R . . C19 C 0.2413(3) 0.8140(4) 0.23628(14) 0.0416(8) Uani 1 1 d . A . H19 H 0.3025 0.8723 0.2541 0.050 Uiso 1 1 calc R . . C20 C 0.2040(3) 0.6986(4) 0.27062(17) 0.0522(10) Uani 1 1 d D . . C21A C 0.018(2) 0.591(2) 0.2994(10) 0.099(3) Uani 0.297(10) 1 d P A 1 H21A H 0.0794 0.5338 0.3205 0.149 Uiso 0.297(10) 1 calc PR A 1 H21B H -0.0377 0.5351 0.2740 0.149 Uiso 0.297(10) 1 calc PR A 1 H21C H -0.0295 0.6388 0.3259 0.149 Uiso 0.297(10) 1 calc PR A 1 C21B C 0.0694(8) 0.5012(10) 0.2698(4) 0.099(3) Uani 0.703(10) 1 d P A 2 H21D H 0.1386 0.4386 0.2764 0.149 Uiso 0.703(10) 1 calc PR A 2 H21E H 0.0032 0.4582 0.2452 0.149 Uiso 0.703(10) 1 calc PR A 2 H21F H 0.0402 0.5246 0.3060 0.149 Uiso 0.703(10) 1 calc PR A 2 C22 C 0.1303(3) 0.8852(3) 0.03171(15) 0.0425(8) Uani 1 1 d . . . C23 C 0.2165(5) 0.9553(6) -0.05191(17) 0.0834(15) Uani 1 1 d . . . H23A H 0.1868 0.8717 -0.0709 0.125 Uiso 1 1 calc R . . H23B H 0.2965 0.9789 -0.0637 0.125 Uiso 1 1 calc R . . H23C H 0.1584 1.0288 -0.0623 0.125 Uiso 1 1 calc R . . C24 C 0.0226(3) 0.6702(3) 0.12465(16) 0.0461(9) Uani 1 1 d D . . C25 C -0.0917(3) 0.6725(4) 0.14145(19) 0.0628(11) Uani 1 1 d D . . H25 H -0.1170 0.7511 0.1599 0.075 Uiso 1 1 calc R . . C26 C -0.1740(4) 0.5639(4) 0.13276(19) 0.0631(11) Uani 1 1 d D . . H26 H -0.2525 0.5706 0.1456 0.076 Uiso 1 1 calc R . . C27 C -0.1435(4) 0.4514(5) 0.1067(3) 0.0857(16) Uani 1 1 d D . . H27 H -0.1929 0.3726 0.1068 0.103 Uiso 1 1 calc R . . C28 C -0.0350(5) 0.4513(5) 0.0784(3) 0.0902(16) Uani 1 1 d D . . H28 H -0.0190 0.3790 0.0540 0.108 Uiso 1 1 calc R . . C29 C 0.0480(4) 0.5612(5) 0.0875(2) 0.0761(13) Uani 1 1 d D . . H29 H 0.1203 0.5628 0.0691 0.091 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0446(13) 0.0347(13) 0.0350(12) -0.0027(10) -0.0063(10) -0.0046(10) O2 0.083(2) 0.0639(19) 0.0582(17) -0.0147(14) -0.0113(15) 0.0276(17) O3A 0.037(6) 0.069(9) 0.079(9) 0.045(7) 0.000(5) -0.015(6) O4A 0.069(3) 0.087(4) 0.031(4) 0.017(4) 0.001(3) -0.005(2) O3B 0.082(4) 0.076(4) 0.074(4) 0.037(3) -0.021(3) -0.038(3) O4B 0.069(3) 0.087(4) 0.031(4) 0.017(4) 0.001(3) -0.005(2) O5 0.0579(16) 0.0771(19) 0.0384(13) -0.0068(13) 0.0060(12) -0.0059(14) O6 0.0669(18) 0.074(2) 0.0605(17) -0.0076(15) -0.0269(15) -0.0139(15) C1 0.0326(16) 0.0329(18) 0.0324(16) -0.0042(14) 0.0019(13) -0.0011(14) C2 0.0293(16) 0.0347(18) 0.0432(19) -0.0042(15) -0.0004(14) 0.0002(13) C3 0.0295(16) 0.0336(18) 0.053(2) -0.0101(16) 0.0028(14) -0.0008(14) C4 0.0339(16) 0.0311(17) 0.0416(19) -0.0030(14) 0.0094(14) 0.0003(13) C5 0.0310(16) 0.0361(18) 0.0319(16) -0.0031(14) -0.0028(13) -0.0021(14) C6 0.0454(19) 0.041(2) 0.0401(19) -0.0039(16) 0.0038(15) -0.0075(17) C7 0.0442(19) 0.042(2) 0.0345(18) -0.0016(15) 0.0042(14) -0.0157(15) C8 0.061(2) 0.053(2) 0.043(2) -0.0110(18) 0.0116(17) -0.0159(18) C9 0.073(3) 0.072(3) 0.039(2) -0.019(2) 0.0128(19) -0.031(2) C10 0.062(3) 0.082(3) 0.036(2) 0.005(2) -0.0046(18) -0.028(2) C11 0.061(2) 0.066(3) 0.044(2) 0.010(2) -0.0065(18) -0.016(2) C12 0.051(2) 0.050(2) 0.0374(19) -0.0009(16) -0.0007(16) -0.0115(17) C13 0.0352(17) 0.0302(17) 0.0350(17) -0.0026(14) 0.0003(13) -0.0029(13) C14 0.0388(18) 0.047(2) 0.0435(19) 0.0017(17) -0.0029(15) -0.0032(15) C15 0.061(2) 0.050(2) 0.044(2) 0.0093(18) -0.0056(17) 0.0026(18) C16 0.072(3) 0.050(2) 0.047(2) 0.0102(18) 0.016(2) -0.005(2) C17 0.048(2) 0.062(3) 0.067(3) 0.009(2) 0.016(2) -0.0114(19) C18 0.0370(19) 0.050(2) 0.049(2) 0.0036(17) 0.0015(15) -0.0045(16) C19 0.0393(18) 0.040(2) 0.046(2) -0.0009(16) 0.0075(15) -0.0024(15) C20 0.045(2) 0.056(2) 0.053(2) 0.0158(19) -0.0017(18) -0.0046(18) C21A 0.098(6) 0.078(6) 0.116(7) 0.052(5) -0.011(5) -0.043(5) C21B 0.098(6) 0.078(6) 0.116(7) 0.052(5) -0.011(5) -0.043(5) C22 0.047(2) 0.0317(18) 0.046(2) -0.0087(16) -0.0093(17) 0.0042(15) C23 0.107(4) 0.101(4) 0.043(2) -0.006(2) 0.016(2) 0.001(3) C24 0.0392(19) 0.0315(18) 0.068(2) -0.0102(17) 0.0091(17) -0.0037(14) C25 0.046(2) 0.045(2) 0.099(3) -0.018(2) 0.018(2) -0.0072(18) C26 0.045(2) 0.061(3) 0.086(3) -0.007(2) 0.017(2) -0.0139(19) C27 0.051(3) 0.051(3) 0.156(5) -0.009(3) 0.015(3) -0.017(2) C28 0.086(3) 0.055(3) 0.129(5) -0.031(3) 0.006(3) -0.007(3) C29 0.060(3) 0.064(3) 0.107(4) -0.019(3) 0.018(2) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.361(4) . ? O1 C5 1.415(4) . ? O2 C6 1.200(4) . ? O3A C20 1.339(12) . ? O3A C21A 1.46(2) . ? O4A C20 1.152(18) . ? O3B C20 1.351(7) . ? O3B C21B 1.448(8) . ? O4B C20 1.227(8) . ? O5 C22 1.322(4) . ? O5 C23 1.432(5) . ? O6 C22 1.202(4) . ? C1 C5 1.330(4) . ? C1 C2 1.484(4) . ? C1 C4 1.497(4) . ? C2 C3 1.365(5) . ? C2 C22 1.476(5) . ? C3 C24 1.473(5) . ? C3 C4 1.500(4) . ? C4 C19 1.337(5) . ? C5 C13 1.463(4) . ? C6 C7 1.482(5) . ? C7 C12 1.389(5) . ? C7 C8 1.389(5) . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.363(6) . ? C9 H9 0.9300 . ? C10 C11 1.370(6) . ? C10 H10 0.9300 . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.384(4) . ? C13 C18 1.391(4) . ? C14 C15 1.381(5) . ? C14 H14 0.9300 . ? C15 C16 1.369(5) . ? C15 H15 0.9300 . ? C16 C17 1.364(6) . ? C16 H16 0.9300 . ? C17 C18 1.377(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.457(5) . ? C19 H19 0.9300 . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.333(5) . ? C24 C29 1.411(6) . ? C25 C26 1.375(5) . ? C25 H25 0.9300 . ? C26 C27 1.307(6) . ? C26 H26 0.9300 . ? C27 C28 1.404(7) . ? C27 H27 0.9300 . ? C28 C29 1.390(6) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C5 117.6(2) . . ? C20 O3A C21A 119.8(12) . . ? C20 O3B C21B 117.8(5) . . ? C22 O5 C23 117.2(3) . . ? C5 C1 C2 139.0(3) . . ? C5 C1 C4 134.1(3) . . ? C2 C1 C4 86.9(2) . . ? C3 C2 C22 130.3(3) . . ? C3 C2 C1 93.7(3) . . ? C22 C2 C1 135.5(3) . . ? C2 C3 C24 131.9(3) . . ? C2 C3 C4 91.3(2) . . ? C24 C3 C4 136.7(3) . . ? C19 C4 C1 132.2(3) . . ? C19 C4 C3 139.2(3) . . ? C1 C4 C3 87.9(2) . . ? C1 C5 O1 114.7(3) . . ? C1 C5 C13 128.7(3) . . ? O1 C5 C13 116.4(2) . . ? O2 C6 O1 122.8(3) . . ? O2 C6 C7 126.0(3) . . ? O1 C6 C7 111.2(3) . . ? C12 C7 C8 119.4(3) . . ? C12 C7 C6 122.0(3) . . ? C8 C7 C6 118.6(3) . . ? C9 C8 C7 119.3(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.8(4) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 120.4(4) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C14 C13 C18 118.7(3) . . ? C14 C13 C5 120.4(3) . . ? C18 C13 C5 120.9(3) . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 121.0(3) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C13 119.9(3) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C4 C19 C20 127.2(3) . . ? C4 C19 H19 116.4 . . ? C20 C19 H19 116.4 . . ? O4A C20 O4B 22.5(10) . . ? O4A C20 O3A 128.5(15) . . ? O4B C20 O3A 115.1(7) . . ? O4A C20 O3B 117.8(17) . . ? O4B C20 O3B 121.7(7) . . ? O3A C20 O3B 39.9(6) . . ? O4A C20 C19 121.8(16) . . ? O4B C20 C19 126.0(6) . . ? O3A C20 C19 108.9(6) . . ? O3B C20 C19 112.0(4) . . ? O3B C21B H21D 109.5 . . ? O3B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? O3B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? O6 C22 O5 124.9(3) . . ? O6 C22 C2 123.6(3) . . ? O5 C22 C2 111.5(3) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 116.1(3) . . ? C25 C24 C3 123.4(3) . . ? C29 C24 C3 119.3(3) . . ? C24 C25 C26 123.1(4) . . ? C24 C25 H25 118.5 . . ? C26 C25 H25 118.5 . . ? C27 C26 C25 120.9(4) . . ? C27 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C26 C27 C28 119.0(4) . . ? C26 C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C29 C28 C27 118.8(4) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C28 C29 C24 120.1(4) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.949 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.057 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C12 H12 O1 0.9300 2.3900 2.712(4) 100.00 . yes C14 H14 O6 0.9300 2.5600 3.269(5) 133.00 3_575 yes C19 H19 O1 0.9300 2.5200 3.103(4) 121.00 . yes C28 H28 O6 0.9300 2.5500 3.451(6) 163.00 3_565 yes