# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year 2010 _journal_page_first ? _journal_volume ? _publ_contact_author_name 'Prof. Menahem Kaftory' _publ_contact_author_email kaftory@techunix.technion.ac.il loop_ _publ_author_name 'Irena Zouev' 'Deng-Ke Cao' 'Thekku V. Sreevidya' 'Marina Telzinski' 'Mark Botoshansky' ; M.Kaftory ; data_(1) _database_code_depnum_ccdc_archive 'CCDC 806062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-Acetyl-anthracene ; _chemical_name_common 9-Acetyl-anthracene _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 O' _chemical_formula_sum 'C16 H12 O' _chemical_formula_weight 220.26 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.319(2) _cell_length_b 16.294(3) _cell_length_c 9.718(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.50(3) _cell_angle_gamma 90.00 _cell_volume 1168.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7924 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.05 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.077 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7924 _diffrn_reflns_av_R_equivalents 0.096 _diffrn_reflns_av_sigmaI/netI 0.1007 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.13 _reflns_number_total 2058 _reflns_number_gt 938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2058 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 0.769 _refine_ls_restrained_S_all 0.769 _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 0.4759(2) 0.08562(11) 0.10149(17) 0.0772(6) Uani 1 1 d . . . C1 C 0.2956(3) 0.02867(14) 0.2059(2) 0.0478(6) Uani 1 1 d . . . C2 C 0.2122(3) 0.08624(14) 0.2593(2) 0.0483(5) Uani 1 1 d . . . C3 C 0.1537(3) 0.16456(15) 0.1888(3) 0.0606(6) Uani 1 1 d . . . H3 H 0.1790 0.1802 0.1088 0.073 Uiso 1 1 calc R . . C4 C 0.0624(3) 0.21666(16) 0.2354(3) 0.0711(7) Uani 1 1 d . . . H4 H 0.0232 0.2669 0.1855 0.085 Uiso 1 1 calc R . . C5 C 0.0259(3) 0.19579(17) 0.3592(3) 0.0708(7) Uani 1 1 d . . . H5 H -0.0394 0.2317 0.3889 0.085 Uiso 1 1 calc R . . C6 C 0.0855(3) 0.12382(16) 0.4346(3) 0.0611(7) Uani 1 1 d . . . H6 H 0.0657 0.1119 0.5190 0.073 Uiso 1 1 calc R . . C7 C 0.1787(3) 0.06562(14) 0.3871(2) 0.0490(6) Uani 1 1 d . . . C8 C 0.2327(3) -0.01063(14) 0.4573(2) 0.0528(6) Uani 1 1 d . . . H8 H 0.2161 -0.0230 0.5433 0.063 Uiso 1 1 calc R . . C9 C 0.3110(3) -0.06899(14) 0.4024(2) 0.0496(6) Uani 1 1 d . . . C10 C 0.3598(3) -0.14831(16) 0.4707(3) 0.0636(7) Uani 1 1 d . . . H10 H 0.3417 -0.1613 0.5557 0.076 Uiso 1 1 calc R . . C11 C 0.4318(3) -0.20481(15) 0.4142(3) 0.0699(7) Uani 1 1 d . . . H11 H 0.4613 -0.2566 0.4594 0.084 Uiso 1 1 calc R . . C12 C 0.4625(3) -0.18585(16) 0.2874(3) 0.0675(7) Uani 1 1 d . . . H12 H 0.5125 -0.2255 0.2496 0.081 Uiso 1 1 calc R . . C13 C 0.4208(3) -0.11104(16) 0.2186(2) 0.0592(6) Uani 1 1 d . . . H13 H 0.4433 -0.0998 0.1353 0.071 Uiso 1 1 calc R . . C14 C 0.3426(3) -0.04945(14) 0.2735(2) 0.0475(5) Uani 1 1 d . . . C15 C 0.3351(3) 0.05212(14) 0.0749(2) 0.0535(6) Uani 1 1 d . . . C16 C 0.1964(3) 0.03404(19) -0.0863(3) 0.0902(9) Uani 1 1 d . . . H16A H 0.0839 0.0596 -0.1057 0.135 Uiso 1 1 calc R . . H16B H 0.1794 -0.0242 -0.0997 0.135 Uiso 1 1 calc R . . H16C H 0.2361 0.0551 -0.1578 0.135 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 0.0763(12) 0.0925(14) 0.0762(11) -0.0102(10) 0.0466(10) -0.0278(11) C1 0.0417(13) 0.0578(17) 0.0456(12) -0.0039(11) 0.0217(11) -0.0073(11) C2 0.0435(12) 0.0539(15) 0.0452(12) -0.0004(11) 0.0184(11) -0.0068(11) C3 0.0586(15) 0.0634(18) 0.0614(14) 0.0061(13) 0.0291(13) 0.0056(13) C4 0.0754(18) 0.0653(19) 0.0740(16) 0.0077(13) 0.0358(15) 0.0113(15) C5 0.0642(17) 0.076(2) 0.0734(16) -0.0123(15) 0.0326(15) 0.0053(15) C6 0.0590(15) 0.072(2) 0.0583(14) -0.0124(13) 0.0322(13) -0.0087(13) C7 0.0452(12) 0.0544(17) 0.0494(12) -0.0077(11) 0.0236(11) -0.0087(11) C8 0.0538(15) 0.0616(17) 0.0449(12) -0.0045(11) 0.0244(12) -0.0143(12) C9 0.0468(13) 0.0514(16) 0.0470(12) -0.0035(11) 0.0185(11) -0.0114(11) C10 0.0639(16) 0.0638(19) 0.0567(14) 0.0053(13) 0.0223(13) -0.0089(14) C11 0.0780(18) 0.0528(18) 0.0681(16) 0.0026(13) 0.0245(15) -0.0020(14) C12 0.0698(17) 0.0573(18) 0.0683(15) -0.0090(14) 0.0259(14) 0.0025(14) C13 0.0603(15) 0.0621(18) 0.0547(13) -0.0091(12) 0.0263(13) -0.0066(13) C14 0.0441(13) 0.0524(16) 0.0444(11) -0.0075(11) 0.0192(11) -0.0116(11) C15 0.0525(14) 0.0594(16) 0.0530(13) 0.0010(11) 0.0280(12) -0.0026(12) C16 0.0694(18) 0.150(3) 0.0467(14) -0.0044(15) 0.0231(14) -0.0145(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.208(2) . ? C1 C14 1.403(3) . ? C1 C2 1.402(3) . ? C1 C15 1.503(3) . ? C2 C3 1.424(3) . ? C2 C7 1.432(3) . ? C3 C4 1.349(3) . ? C3 H3 0.9300 . ? C4 C5 1.412(3) . ? C4 H4 0.9300 . ? C5 C6 1.350(3) . ? C5 H5 0.9300 . ? C6 C7 1.429(3) . ? C6 H6 0.9300 . ? C7 C8 1.388(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9300 . ? C9 C10 1.424(3) . ? C9 C14 1.429(3) . ? C10 C11 1.345(3) . ? C10 H10 0.9300 . ? C11 C12 1.404(3) . ? C11 H11 0.9300 . ? C12 C13 1.356(3) . ? C12 H12 0.9300 . ? C13 C14 1.427(3) . ? C13 H13 0.9300 . ? C15 C16 1.485(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C14 C1 C2 120.80(18) . . ? C14 C1 C15 120.33(18) . . ? C2 C1 C15 118.9(2) . . ? C1 C2 C3 122.63(18) . . ? C1 C2 C7 119.5(2) . . ? C3 C2 C7 117.86(19) . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.3(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 122.40(19) . . ? C8 C7 C2 119.18(19) . . ? C6 C7 C2 118.4(2) . . ? C7 C8 C9 121.73(18) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C10 121.69(19) . . ? C8 C9 C14 119.5(2) . . ? C10 C9 C14 118.8(2) . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 121.4(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C1 C14 C13 122.65(18) . . ? C1 C14 C9 119.25(19) . . ? C13 C14 C9 118.1(2) . . ? O1 C15 C16 121.32(19) . . ? O1 C15 C1 120.2(2) . . ? C16 C15 C1 118.43(19) . . ? 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 . . ? 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 C14 C1 C2 C3 -176.6(2) . . . . ? C15 C1 C2 C3 3.7(3) . . . . ? C14 C1 C2 C7 1.6(3) . . . . ? C15 C1 C2 C7 -178.13(18) . . . . ? C1 C2 C3 C4 175.3(2) . . . . ? C7 C2 C3 C4 -2.9(3) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? C4 C5 C6 C7 -3.0(4) . . . . ? C5 C6 C7 C8 -176.4(2) . . . . ? C5 C6 C7 C2 1.7(3) . . . . ? C1 C2 C7 C8 1.1(3) . . . . ? C3 C2 C7 C8 179.4(2) . . . . ? C1 C2 C7 C6 -177.01(18) . . . . ? C3 C2 C7 C6 1.3(3) . . . . ? C6 C7 C8 C9 175.07(19) . . . . ? C2 C7 C8 C9 -3.0(3) . . . . ? C7 C8 C9 C10 -177.5(2) . . . . ? C7 C8 C9 C14 2.1(3) . . . . ? C8 C9 C10 C11 178.5(2) . . . . ? C14 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 0.9(3) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C2 C1 C14 C13 177.33(19) . . . . ? C15 C1 C14 C13 -3.0(3) . . . . ? C2 C1 C14 C9 -2.4(3) . . . . ? C15 C1 C14 C9 177.25(18) . . . . ? C12 C13 C14 C1 -179.5(2) . . . . ? C12 C13 C14 C9 0.3(3) . . . . ? C8 C9 C14 C1 0.6(3) . . . . ? C10 C9 C14 C1 -179.7(2) . . . . ? C8 C9 C14 C13 -179.15(18) . . . . ? C10 C9 C14 C13 0.5(3) . . . . ? C14 C1 C15 O1 -91.7(3) . . . . ? C2 C1 C15 O1 87.9(3) . . . . ? C14 C1 C15 C16 89.0(3) . . . . ? C2 C1 C15 C16 -91.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.134 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.028 data_(3d) _database_code_depnum_ccdc_archive 'CCDC 806063' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Isopropyl anthracene-9-carboxylate dimer' _chemical_melting_point ? _chemical_formula_moiety 'C36 H32 O4' _chemical_formula_sum 'C36 H32 O4' _chemical_formula_weight 528.62 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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.368(2) _cell_length_b 15.431(3) _cell_length_c 15.462(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2712.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3508 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.81 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.083 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17692 _diffrn_reflns_av_R_equivalents 0.118 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.81 _reflns_number_total 3176 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3176 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2109 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.16159(19) 0.51627(15) 0.48728(15) 0.0502(6) Uani 1 1 d . . . O2 O 0.19267(17) 0.44119(12) 0.60893(13) 0.0359(5) Uani 1 1 d . . . C1 C 0.3634(2) 0.48397(16) 0.53072(17) 0.0266(6) Uani 1 1 d . . . C2 C 0.4177(2) 0.39353(16) 0.53904(16) 0.0272(6) Uani 1 1 d . . . C3 C 0.3550(3) 0.31693(15) 0.52807(17) 0.0309(6) Uani 1 1 d . . . H3 H 0.2746 0.3189 0.5169 0.037 Uiso 1 1 calc R . . C4 C 0.4122(3) 0.23714(17) 0.53377(18) 0.0343(7) Uani 1 1 d . . . H4 H 0.3702 0.1861 0.5253 0.041 Uiso 1 1 calc R . . C5 C 0.5309(3) 0.23387(17) 0.55188(17) 0.0336(7) Uani 1 1 d . . . H5 H 0.5684 0.1805 0.5569 0.040 Uiso 1 1 calc R . . C6 C 0.5944(3) 0.30954(16) 0.56255(17) 0.0307(7) Uani 1 1 d . . . H6 H 0.6743 0.3070 0.5752 0.037 Uiso 1 1 calc R . . C7 C 0.5385(2) 0.38969(16) 0.55435(16) 0.0275(6) Uani 1 1 d . . . C8 C 0.6053(2) 0.47470(16) 0.56217(17) 0.0282(6) Uani 1 1 d . . . H8 H 0.6796 0.4627 0.5920 0.034 Uiso 1 1 calc R . . C9 C 0.5345(2) 0.53550(16) 0.61850(16) 0.0271(6) Uani 1 1 d . . . C10 C 0.5858(3) 0.58487(16) 0.68341(17) 0.0305(6) Uani 1 1 d . . . H10 H 0.6663 0.5809 0.6934 0.037 Uiso 1 1 calc R . . C11 C 0.5177(3) 0.64000(17) 0.73349(18) 0.0354(7) Uani 1 1 d . . . H11 H 0.5524 0.6731 0.7768 0.042 Uiso 1 1 calc R . . C12 C 0.3981(3) 0.64555(16) 0.71874(18) 0.0343(7) Uani 1 1 d . . . H12 H 0.3524 0.6825 0.7524 0.041 Uiso 1 1 calc R . . C13 C 0.3456(3) 0.59652(16) 0.65420(17) 0.0307(6) Uani 1 1 d . . . H13 H 0.2651 0.6011 0.6445 0.037 Uiso 1 1 calc R . . C14 C 0.4131(2) 0.54041(15) 0.60386(17) 0.0284(6) Uani 1 1 d . . . C15 C 0.2286(3) 0.48226(17) 0.53776(17) 0.0319(7) Uani 1 1 d . . . C16 C 0.0657(3) 0.44026(17) 0.6243(2) 0.0354(7) Uani 1 1 d . . . H16A H 0.0246 0.4220 0.5724 0.042 Uiso 1 1 calc R . . H16B H 0.0386 0.4978 0.6397 0.042 Uiso 1 1 calc R . . C17 C 0.0422(3) 0.37838(19) 0.6964(2) 0.0407(8) Uani 1 1 d . . . H17A H 0.0851 0.3963 0.7475 0.049 Uiso 1 1 calc R . . H17B H 0.0691 0.3210 0.6802 0.049 Uiso 1 1 calc R . . C18 C -0.0898(3) 0.3757(2) 0.7163(2) 0.0454(8) Uani 1 1 d . . . H18A H -0.1028 0.3432 0.7684 0.054 Uiso 1 1 calc R . . H18B H -0.1308 0.3486 0.6692 0.054 Uiso 1 1 calc R . . H18C H -0.1186 0.4337 0.7239 0.054 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 0.0302(13) 0.0691(14) 0.0514(14) 0.0251(12) -0.0020(10) 0.0051(11) O2 0.0267(12) 0.0405(11) 0.0406(12) 0.0041(9) 0.0023(9) -0.0005(8) C1 0.0238(15) 0.0282(13) 0.0277(14) 0.0016(11) 0.0033(11) -0.0020(11) C2 0.0303(17) 0.0290(14) 0.0223(13) -0.0013(10) 0.0038(11) 0.0014(11) C3 0.0291(16) 0.0310(14) 0.0325(15) 0.0011(11) 0.0011(12) -0.0011(12) C4 0.0397(19) 0.0284(14) 0.0350(16) -0.0011(11) 0.0052(13) -0.0052(12) C5 0.0430(19) 0.0266(14) 0.0311(15) -0.0009(11) 0.0033(13) 0.0056(12) C6 0.0344(18) 0.0324(15) 0.0254(14) 0.0026(11) 0.0014(12) 0.0031(11) C7 0.0336(17) 0.0286(14) 0.0202(13) 0.0002(10) 0.0030(11) -0.0005(11) C8 0.0283(16) 0.0304(14) 0.0259(14) -0.0018(11) -0.0032(11) 0.0002(11) C9 0.0319(17) 0.0236(13) 0.0257(14) 0.0040(10) 0.0007(11) -0.0014(10) C10 0.0327(17) 0.0306(14) 0.0283(14) 0.0006(11) -0.0021(12) -0.0005(11) C11 0.046(2) 0.0323(14) 0.0280(15) -0.0059(12) -0.0015(13) -0.0053(13) C12 0.043(2) 0.0270(14) 0.0326(15) -0.0055(12) 0.0082(13) 0.0024(12) C13 0.0310(16) 0.0315(14) 0.0294(15) 0.0028(11) 0.0043(12) -0.0009(11) C14 0.0322(17) 0.0269(13) 0.0261(14) 0.0017(10) 0.0028(12) -0.0028(11) C15 0.0362(18) 0.0292(14) 0.0302(15) 0.0010(11) 0.0024(13) 0.0000(12) C16 0.0272(16) 0.0376(15) 0.0414(17) -0.0027(13) 0.0001(13) 0.0010(12) C17 0.045(2) 0.0365(16) 0.0402(17) 0.0010(13) 0.0040(15) -0.0014(13) C18 0.042(2) 0.0524(18) 0.0414(18) 0.0005(14) 0.0075(15) -0.0072(15) _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 C15 1.210(3) . ? O2 C15 1.334(3) . ? O2 C16 1.462(3) . ? C1 C2 1.531(4) . ? C1 C14 1.535(4) . ? C1 C15 1.537(4) . ? C1 C8 1.611(4) 5_666 ? C2 C3 1.391(4) . ? C2 C7 1.395(4) . ? C3 C4 1.395(4) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C4 H4 0.9300 . ? C5 C6 1.382(4) . ? C5 H5 0.9300 . ? C6 C7 1.396(3) . ? C6 H6 0.9300 . ? C7 C8 1.521(3) . ? C8 C9 1.512(3) . ? C8 C1 1.611(4) 5_666 ? C8 H8 0.9800 . ? C9 C10 1.388(4) . ? C9 C14 1.401(4) . ? C10 C11 1.387(4) . ? C10 H10 0.9300 . ? C11 C12 1.381(4) . ? C11 H11 0.9300 . ? C12 C13 1.387(4) . ? C12 H12 0.9300 . ? C13 C14 1.395(4) . ? C13 H13 0.9300 . ? C16 C17 1.492(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.532(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C15 O2 C16 116.1(2) . . ? C2 C1 C14 107.9(2) . . ? C2 C1 C15 112.4(2) . . ? C14 C1 C15 109.0(2) . . ? C2 C1 C8 110.3(2) . 5_666 ? C14 C1 C8 110.5(2) . 5_666 ? C15 C1 C8 106.8(2) . 5_666 ? C3 C2 C7 119.3(2) . . ? C3 C2 C1 123.9(2) . . ? C7 C2 C1 116.7(2) . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 120.1(2) . . ? C6 C7 C8 122.0(2) . . ? C2 C7 C8 117.9(2) . . ? C9 C8 C7 108.4(2) . . ? C9 C8 C1 112.7(2) . 5_666 ? C7 C8 C1 112.4(2) . 5_666 ? C9 C8 H8 107.7 . . ? C7 C8 H8 107.7 . . ? C1 C8 H8 107.7 5_666 . ? C10 C9 C14 120.0(2) . . ? C10 C9 C8 122.2(2) . . ? C14 C9 C8 117.7(2) . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 119.1(2) . . ? C13 C14 C1 124.1(3) . . ? C9 C14 C1 116.8(2) . . ? O1 C15 O2 123.1(3) . . ? O1 C15 C1 125.1(2) . . ? O2 C15 C1 111.8(2) . . ? O2 C16 C17 107.7(2) . . ? O2 C16 H16A 110.2 . . ? C17 C16 H16A 110.2 . . ? O2 C16 H16B 110.2 . . ? C17 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? C16 C17 C18 110.1(3) . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? 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 . . ? 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 C14 C1 C2 C3 138.3(3) . . . . ? C15 C1 C2 C3 18.2(4) . . . . ? C8 C1 C2 C3 -100.9(3) 5_666 . . . ? C14 C1 C2 C7 -45.0(3) . . . . ? C15 C1 C2 C7 -165.1(2) . . . . ? C8 C1 C2 C7 75.8(3) 5_666 . . . ? C7 C2 C3 C4 1.1(4) . . . . ? C1 C2 C3 C4 177.7(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C3 C4 C5 C6 -1.5(4) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? C5 C6 C7 C2 2.7(4) . . . . ? C5 C6 C7 C8 -177.7(2) . . . . ? C3 C2 C7 C6 -3.0(4) . . . . ? C1 C2 C7 C6 -179.9(2) . . . . ? C3 C2 C7 C8 177.4(2) . . . . ? C1 C2 C7 C8 0.5(3) . . . . ? C6 C7 C8 C9 -135.3(2) . . . . ? C2 C7 C8 C9 44.3(3) . . . . ? C6 C7 C8 C1 99.5(3) . . . 5_666 ? C2 C7 C8 C1 -80.9(3) . . . 5_666 ? C7 C8 C9 C10 135.5(2) . . . . ? C1 C8 C9 C10 -99.5(3) 5_666 . . . ? C7 C8 C9 C14 -44.0(3) . . . . ? C1 C8 C9 C14 81.0(3) 5_666 . . . ? C14 C9 C10 C11 -0.7(4) . . . . ? C8 C9 C10 C11 179.8(2) . . . . ? C9 C10 C11 C12 0.2(4) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C9 -1.1(4) . . . . ? C12 C13 C14 C1 -179.6(2) . . . . ? C10 C9 C14 C13 1.2(4) . . . . ? C8 C9 C14 C13 -179.4(2) . . . . ? C10 C9 C14 C1 179.8(2) . . . . ? C8 C9 C14 C1 -0.7(3) . . . . ? C2 C1 C14 C13 -136.2(3) . . . . ? C15 C1 C14 C13 -14.0(3) . . . . ? C8 C1 C14 C13 103.2(3) 5_666 . . . ? C2 C1 C14 C9 45.2(3) . . . . ? C15 C1 C14 C9 167.4(2) . . . . ? C8 C1 C14 C9 -75.4(3) 5_666 . . . ? C16 O2 C15 O1 -0.9(4) . . . . ? C16 O2 C15 C1 176.6(2) . . . . ? C2 C1 C15 O1 -129.8(3) . . . . ? C14 C1 C15 O1 110.7(3) . . . . ? C8 C1 C15 O1 -8.7(4) 5_666 . . . ? C2 C1 C15 O2 52.7(3) . . . . ? C14 C1 C15 O2 -66.8(3) . . . . ? C8 C1 C15 O2 173.8(2) 5_666 . . . ? C15 O2 C16 C17 169.7(2) . . . . ? O2 C16 C17 C18 179.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.574 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.067 data_(4c) _database_code_depnum_ccdc_archive 'CCDC 806064' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Isopropyl anthracene-9-carboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 O2' _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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.919(2) _cell_length_b 8.734(2) _cell_length_c 18.506(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.75(3) _cell_angle_gamma 90.00 _cell_volume 1431.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9176 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.02 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.079 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9990 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2526 _reflns_number_gt 1359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0790P)^2^+0.1153P] 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 2510 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1757 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.1935(3) 0.6655(3) 0.34150(17) 0.1684(15) Uani 1 1 d . . . O2 O 0.10874(18) 0.47116(19) 0.26016(11) 0.0734(6) Uani 1 1 d . . . C1 C 0.3206(3) 0.4273(3) 0.38175(15) 0.0591(7) Uani 1 1 d . . . C2 C 0.4430(3) 0.3888(3) 0.36745(16) 0.0599(7) Uani 1 1 d . . . C3 C 0.4652(3) 0.4525(3) 0.30284(18) 0.0779(8) Uani 1 1 d . . . H3 H 0.3955 0.5222 0.2679 0.094 Uiso 1 1 calc R . . C4 C 0.5860(4) 0.4134(4) 0.2915(2) 0.0965(11) Uani 1 1 d . . . H4 H 0.5990 0.4571 0.2492 0.116 Uiso 1 1 calc R . . C5 C 0.6922(4) 0.3070(4) 0.3430(2) 0.0958(11) Uani 1 1 d . . . H5 H 0.7738 0.2798 0.3339 0.115 Uiso 1 1 calc R . . C6 C 0.6771(3) 0.2441(4) 0.4054(2) 0.0846(9) Uani 1 1 d . . . H6 H 0.7493 0.1751 0.4393 0.102 Uiso 1 1 calc R . . C7 C 0.5526(3) 0.2820(3) 0.41975(17) 0.0633(7) Uani 1 1 d . . . C8 C 0.5353(3) 0.2210(3) 0.48392(18) 0.0710(8) Uani 1 1 d . . . H8 H 0.6070 0.1518 0.5179 0.085 Uiso 1 1 calc R . . C9 C 0.4155(3) 0.2586(3) 0.49984(16) 0.0642(7) Uani 1 1 d . . . C10 C 0.3987(4) 0.1969(4) 0.56654(18) 0.0844(9) Uani 1 1 d . . . H10 H 0.4701 0.1277 0.6009 0.101 Uiso 1 1 calc R . . C11 C 0.2827(5) 0.2360(5) 0.5809(2) 0.0996(11) Uani 1 1 d . . . H11 H 0.2753 0.1954 0.6255 0.120 Uiso 1 1 calc R . . C12 C 0.1708(4) 0.3392(4) 0.5285(3) 0.0985(11) Uani 1 1 d . . . H12 H 0.0891 0.3641 0.5381 0.118 Uiso 1 1 calc R . . C13 C 0.1824(3) 0.4013(4) 0.4647(2) 0.0827(9) Uani 1 1 d . . . H13 H 0.1084 0.4692 0.4312 0.099 Uiso 1 1 calc R . . C14 C 0.3041(3) 0.3661(3) 0.44722(17) 0.0626(7) Uani 1 1 d . . . C15 C 0.2039(3) 0.5361(3) 0.32679(17) 0.0728(8) Uani 1 1 d . . . C16 C -0.0150(3) 0.5628(3) 0.19885(18) 0.0699(8) Uani 1 1 d . . . H16 H 0.0160 0.6703 0.2030 0.084 Uiso 1 1 calc R . . C17 C -0.0390(3) 0.4998(4) 0.11908(18) 0.0921(10) Uani 1 1 d . . . H17A H 0.0528 0.5083 0.1139 0.138 Uiso 1 1 calc R . . H17B H -0.1176 0.5563 0.0764 0.138 Uiso 1 1 calc R . . H17C H -0.0677 0.3940 0.1156 0.138 Uiso 1 1 calc R . . C18 C -0.1498(3) 0.5495(3) 0.21439(19) 0.0875(10) Uani 1 1 d . . . H18A H -0.1766 0.4436 0.2132 0.131 Uiso 1 1 calc R . . H18B H -0.2329 0.6044 0.1734 0.131 Uiso 1 1 calc R . . H18C H -0.1266 0.5919 0.2665 0.131 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 0.167(2) 0.0569(16) 0.140(2) -0.0308(15) -0.0569(18) 0.0417(15) O2 0.0603(10) 0.0452(11) 0.0798(13) 0.0061(10) 0.0006(9) 0.0056(8) C1 0.0642(15) 0.0381(14) 0.0556(16) -0.0048(12) 0.0098(13) 0.0043(12) C2 0.0562(15) 0.0470(15) 0.0614(17) -0.0138(13) 0.0130(13) 0.0004(12) C3 0.0790(19) 0.073(2) 0.0659(19) -0.0012(16) 0.0189(15) -0.0050(15) C4 0.087(2) 0.113(3) 0.088(2) -0.013(2) 0.039(2) -0.017(2) C5 0.077(2) 0.100(3) 0.108(3) -0.027(2) 0.039(2) 0.000(2) C6 0.0636(18) 0.082(2) 0.092(2) -0.0118(19) 0.0207(17) 0.0126(15) C7 0.0604(16) 0.0498(16) 0.0613(18) -0.0094(14) 0.0111(14) 0.0035(13) C8 0.0570(16) 0.0604(18) 0.0688(19) -0.0076(15) 0.0044(14) 0.0103(13) C9 0.0694(17) 0.0525(16) 0.0489(16) -0.0068(13) 0.0073(13) 0.0031(13) C10 0.094(2) 0.075(2) 0.064(2) -0.0049(16) 0.0164(17) -0.0020(18) C11 0.122(3) 0.100(3) 0.076(2) -0.014(2) 0.045(2) -0.011(2) C12 0.101(3) 0.097(3) 0.109(3) -0.029(2) 0.058(2) -0.002(2) C13 0.090(2) 0.070(2) 0.084(2) -0.0114(18) 0.0353(18) 0.0087(16) C14 0.0576(15) 0.0497(16) 0.0666(18) -0.0190(14) 0.0156(14) 0.0008(12) C15 0.0703(16) 0.0429(16) 0.075(2) -0.0077(15) 0.0057(15) 0.0080(13) C16 0.0533(15) 0.0457(16) 0.084(2) 0.0186(14) 0.0074(14) 0.0045(12) C17 0.0816(19) 0.092(2) 0.079(2) 0.0136(19) 0.0150(16) 0.0033(18) C18 0.0709(18) 0.071(2) 0.110(3) 0.0206(18) 0.0311(17) 0.0139(16) _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 C15 1.178(3) . ? O2 C15 1.298(3) . ? O2 C16 1.477(3) . ? C1 C2 1.395(3) . ? C1 C14 1.400(4) . ? C1 C15 1.489(3) . ? C2 C3 1.423(4) . ? C2 C7 1.428(4) . ? C3 C4 1.350(4) . ? C3 H3 0.9300 . ? C4 C5 1.406(5) . ? C4 H4 0.9300 . ? C5 C6 1.346(4) . ? C5 H5 0.9300 . ? C6 C7 1.415(4) . ? C6 H6 0.9300 . ? C7 C8 1.381(4) . ? C8 C9 1.386(4) . ? C8 H8 0.9300 . ? C9 C10 1.424(4) . ? C9 C14 1.443(4) . ? C10 C11 1.337(4) . ? C10 H10 0.9300 . ? C11 C12 1.420(5) . ? C11 H11 0.9300 . ? C12 C13 1.352(4) . ? C12 H12 0.9300 . ? C13 C14 1.416(4) . ? C13 H13 0.9300 . ? C16 C17 1.491(4) . ? C16 C18 1.494(3) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C15 O2 C16 119.4(2) . . ? C2 C1 C14 121.5(2) . . ? C2 C1 C15 120.0(3) . . ? C14 C1 C15 118.5(2) . . ? C1 C2 C3 122.8(3) . . ? C1 C2 C7 119.4(3) . . ? C3 C2 C7 117.8(3) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 121.9(3) . . ? C8 C7 C2 118.9(3) . . ? C6 C7 C2 119.2(3) . . ? C7 C8 C9 122.8(3) . . ? C7 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 122.7(3) . . ? C8 C9 C14 118.7(3) . . ? C10 C9 C14 118.6(3) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 121.9(3) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C1 C14 C13 123.9(3) . . ? C1 C14 C9 118.7(2) . . ? C13 C14 C9 117.4(3) . . ? O1 C15 O2 122.5(3) . . ? O1 C15 C1 125.2(3) . . ? O2 C15 C1 112.3(2) . . ? O2 C16 C17 105.5(2) . . ? O2 C16 C18 108.4(2) . . ? C17 C16 C18 113.8(2) . . ? O2 C16 H16 109.6 . . ? C17 C16 H16 109.6 . . ? C18 C16 H16 109.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.224 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.032 data_(2d) _database_code_depnum_ccdc_archive 'CCDC 812116' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-Carbomethoxy-anthracene dimer ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H24 O4' _chemical_formula_sum 'C32 H24 O4' _chemical_formula_weight 472.51 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' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.585(2) _cell_length_b 13.733(3) _cell_length_c 9.025(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.09(3) _cell_angle_gamma 90.00 _cell_volume 1176.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7747 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.087 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7747 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2075 _reflns_number_gt 1446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.3283P] 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 2075 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 O1 O 0.80825(17) -0.07736(12) 0.29177(19) 0.0625(5) Uani 1 1 d . . . O2 O 0.79399(15) 0.08210(11) 0.25392(16) 0.0496(4) Uani 1 1 d . . . C1 C 0.62965(19) 0.01450(13) 0.39860(19) 0.0302(4) Uani 1 1 d . . . C2 C 0.68008(19) 0.07536(13) 0.5388(2) 0.0324(5) Uani 1 1 d . . . C3 C 0.8206(2) 0.09285(15) 0.5946(2) 0.0389(5) Uani 1 1 d . . . H3 H 0.8914 0.0675 0.5452 0.047 Uiso 1 1 calc R . . C4 C 0.8558(2) 0.14774(16) 0.7233(2) 0.0480(6) Uani 1 1 d . . . H4 H 0.9501 0.1585 0.7605 0.058 Uiso 1 1 calc R . . C5 C 0.7516(2) 0.18650(16) 0.7965(2) 0.0472(6) Uani 1 1 d . . . H5 H 0.7756 0.2242 0.8818 0.057 Uiso 1 1 calc R . . C6 C 0.6120(2) 0.16935(14) 0.7431(2) 0.0396(5) Uani 1 1 d . . . H6 H 0.5421 0.1956 0.7927 0.047 Uiso 1 1 calc R . . C7 C 0.57473(19) 0.11291(14) 0.6152(2) 0.0321(5) Uani 1 1 d . . . C8 C 0.42298(19) 0.09191(13) 0.55448(19) 0.0317(5) Uani 1 1 d . . . H8 H 0.3649 0.1406 0.5965 0.038 Uiso 1 1 calc R . . C9 C 0.40366(19) 0.10669(14) 0.3865(2) 0.0307(4) Uani 1 1 d . . . C10 C 0.2876(2) 0.15468(14) 0.3114(2) 0.0376(5) Uani 1 1 d . . . H10 H 0.2193 0.1795 0.3648 0.045 Uiso 1 1 calc R . . C11 C 0.2725(2) 0.16593(15) 0.1576(2) 0.0427(5) Uani 1 1 d . . . H11 H 0.1947 0.1987 0.1079 0.051 Uiso 1 1 calc R . . C12 C 0.3732(2) 0.12846(17) 0.0782(2) 0.0438(5) Uani 1 1 d . . . H12 H 0.3623 0.1349 -0.0253 0.053 Uiso 1 1 calc R . . C13 C 0.4902(2) 0.08130(14) 0.1522(2) 0.0381(5) Uani 1 1 d . . . H13 H 0.5583 0.0572 0.0980 0.046 Uiso 1 1 calc R . . C14 C 0.50733(19) 0.06950(13) 0.30641(19) 0.0314(4) Uani 1 1 d . . . C15 C 0.7528(2) -0.00133(15) 0.3092(2) 0.0362(5) Uani 1 1 d . . . C16 C 0.9073(2) 0.0765(2) 0.1651(3) 0.0655(8) Uani 1 1 d . . . H16A H 0.9247 0.1400 0.1271 0.098 Uiso 1 1 calc R . . H16B H 0.8818 0.0325 0.0830 0.098 Uiso 1 1 calc R . . H16C H 0.9909 0.0532 0.2260 0.098 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 0.0602(10) 0.0401(11) 0.0967(13) 0.0055(9) 0.0441(9) 0.0144(8) O2 0.0494(9) 0.0422(10) 0.0629(9) 0.0108(7) 0.0274(7) 0.0016(7) C1 0.0331(10) 0.0255(11) 0.0330(10) 0.0000(8) 0.0084(8) 0.0014(8) C2 0.0374(11) 0.0222(11) 0.0379(10) 0.0027(8) 0.0067(8) -0.0007(8) C3 0.0381(11) 0.0326(12) 0.0461(11) 0.0016(9) 0.0063(9) 0.0017(9) C4 0.0443(13) 0.0389(14) 0.0574(13) -0.0019(11) -0.0046(10) -0.0041(10) C5 0.0591(14) 0.0330(13) 0.0465(12) -0.0079(10) -0.0033(10) -0.0022(11) C6 0.0492(13) 0.0277(12) 0.0425(11) -0.0041(9) 0.0086(9) 0.0016(9) C7 0.0394(11) 0.0215(11) 0.0359(10) 0.0022(8) 0.0074(8) 0.0008(8) C8 0.0367(11) 0.0228(11) 0.0368(10) -0.0005(8) 0.0096(8) 0.0035(8) C9 0.0336(10) 0.0225(11) 0.0364(10) 0.0010(8) 0.0064(8) -0.0016(8) C10 0.0356(11) 0.0294(12) 0.0485(12) 0.0033(9) 0.0087(9) 0.0023(9) C11 0.0401(12) 0.0377(13) 0.0484(12) 0.0122(10) 0.0003(9) 0.0034(10) C12 0.0502(13) 0.0453(14) 0.0349(11) 0.0061(9) 0.0020(9) -0.0019(10) C13 0.0458(12) 0.0331(12) 0.0367(11) -0.0006(9) 0.0105(9) 0.0003(9) C14 0.0365(11) 0.0222(11) 0.0359(10) 0.0009(8) 0.0064(8) -0.0025(8) C15 0.0364(11) 0.0326(12) 0.0408(11) 0.0019(9) 0.0091(8) -0.0001(10) C16 0.0500(14) 0.077(2) 0.0764(17) 0.0209(14) 0.0346(13) 0.0024(13) _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 C15 1.192(3) . ? O2 C15 1.331(3) . ? O2 C16 1.440(2) . ? C1 C2 1.536(3) . ? C1 C15 1.536(3) . ? C1 C14 1.537(3) . ? C1 C8 1.622(3) 3_656 ? C2 C3 1.391(3) . ? C2 C7 1.399(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C6 C7 1.394(3) . ? C6 H6 0.9300 . ? C7 C8 1.508(3) . ? C8 C9 1.515(3) . ? C8 C1 1.622(3) 3_656 ? C8 H8 0.9800 . ? C9 C10 1.385(3) . ? C9 C14 1.404(3) . ? C10 C11 1.384(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 C14 1.388(3) . ? C13 H13 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C15 O2 C16 116.69(18) . . ? C2 C1 C15 109.47(15) . . ? C2 C1 C14 107.82(15) . . ? C15 C1 C14 111.68(15) . . ? C2 C1 C8 110.41(14) . 3_656 ? C15 C1 C8 107.45(15) . 3_656 ? C14 C1 C8 110.03(15) . 3_656 ? C3 C2 C7 119.13(18) . . ? C3 C2 C1 124.67(16) . . ? C7 C2 C1 116.18(16) . . ? C4 C3 C2 120.47(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.53(19) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C2 119.62(18) . . ? C6 C7 C8 121.93(17) . . ? C2 C7 C8 118.45(17) . . ? C7 C8 C9 108.29(14) . . ? C7 C8 C1 113.39(14) . 3_656 ? C9 C8 C1 112.54(14) . 3_656 ? C7 C8 H8 107.4 . . ? C9 C8 H8 107.4 . . ? C1 C8 H8 107.4 3_656 . ? C10 C9 C14 119.96(17) . . ? C10 C9 C8 121.98(16) . . ? C14 C9 C8 118.06(16) . . ? C11 C10 C9 120.45(18) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.81(19) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.20(18) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.82(18) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 118.75(18) . . ? C13 C14 C1 125.02(16) . . ? C9 C14 C1 116.19(16) . . ? O1 C15 O2 122.90(19) . . ? O1 C15 C1 125.67(18) . . ? O2 C15 C1 111.42(17) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.155 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.036 data_(3) _database_code_depnum_ccdc_archive 'CCDC 812117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9-carbopropoxy-anthracene _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 O2' _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' O O 0.0106 0.0060 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.858(2) _cell_length_b 8.578(2) _cell_length_c 11.474(2) _cell_angle_alpha 87.89(2) _cell_angle_beta 80.43(2) _cell_angle_gamma 67.09(2) _cell_volume 702.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6338 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.91 _exptl_crystal_description 'long plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.080 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6338 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2421 _reflns_number_gt 1302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1436P)^2^+0.1072P] 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 2423 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1494 _refine_ls_R_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.2797 _refine_ls_wR_factor_gt 0.2391 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 0.7406(4) 0.1353(4) 0.1454(3) 0.1069(12) Uani 1 1 d . . . O2 O 0.8760(4) 0.2682(4) 0.2337(3) 0.1124(12) Uani 1 1 d . . . C1 C 0.5683(4) 0.3128(4) 0.3155(3) 0.0555(9) Uani 1 1 d . . . C2 C 0.4180(4) 0.4552(4) 0.2862(3) 0.0533(9) Uani 1 1 d . . . C3 C 0.4184(5) 0.5287(4) 0.1724(3) 0.0642(10) Uani 1 1 d . . . H3 H 0.5229 0.4821 0.1140 0.077 Uiso 1 1 calc R . . C4 C 0.2707(5) 0.6639(5) 0.1480(3) 0.0700(10) Uani 1 1 d . . . H4 H 0.2752 0.7097 0.0734 0.084 Uiso 1 1 calc R . . C5 C 0.1094(5) 0.7373(5) 0.2336(3) 0.0702(10) Uani 1 1 d . . . H5 H 0.0069 0.8289 0.2148 0.084 Uiso 1 1 calc R . . C6 C 0.1038(5) 0.6743(4) 0.3430(3) 0.0642(10) Uani 1 1 d . . . H6 H -0.0030 0.7244 0.3992 0.077 Uiso 1 1 calc R . . C7 C 0.2561(4) 0.5340(4) 0.3747(3) 0.0540(8) Uani 1 1 d . . . C8 C 0.2555(4) 0.4688(4) 0.4881(3) 0.0574(9) Uani 1 1 d . . . H8 H 0.1517 0.5213 0.5460 0.069 Uiso 1 1 calc R . . C9 C 0.4031(4) 0.3292(4) 0.5180(3) 0.0536(8) Uani 1 1 d . . . C10 C 0.3999(5) 0.2606(5) 0.6330(3) 0.0639(10) Uani 1 1 d . . . H10 H 0.2972 0.3129 0.6916 0.077 Uiso 1 1 calc R . . C12 C 0.7010(5) 0.0398(5) 0.5712(3) 0.0715(10) Uani 1 1 d . . . H12 H 0.7984 -0.0570 0.5894 0.086 Uiso 1 1 calc R . . C13 C 0.7115(5) 0.1017(4) 0.4615(3) 0.0651(10) Uani 1 1 d . . . H13 H 0.8176 0.0479 0.4055 0.078 Uiso 1 1 calc R . . C14 C 0.5640(4) 0.2469(4) 0.4298(3) 0.0547(9) Uani 1 1 d . . . C15 C 0.7326(5) 0.2281(5) 0.2211(3) 0.0689(10) Uani 1 1 d . . . C11 C 0.5435(6) 0.1210(5) 0.6584(3) 0.0752(11) Uani 1 1 d . . . H11 H 0.5385 0.0781 0.7340 0.090 Uiso 1 1 calc R . . C16 C 1.0478(8) 0.1957(8) 0.1463(6) 0.148(3) Uani 1 1 d . . . H16A H 1.1426 0.1110 0.1846 0.177 Uiso 1 1 calc R . . H16B H 1.0222 0.1381 0.0843 0.177 Uiso 1 1 calc R . . C17 C 1.1135(11) 0.2965(9) 0.0996(8) 0.197(4) Uani 1 1 d . . . H17A H 1.1407 0.3518 0.1622 0.236 Uiso 1 1 calc R . . H17B H 1.0159 0.3831 0.0644 0.236 Uiso 1 1 calc R . . C18 C 1.2882(8) 0.2323(8) 0.0058(6) 0.151(3) Uani 1 1 d . . . H18A H 1.3231 0.3248 -0.0205 0.227 Uiso 1 1 calc R . . H18B H 1.2631 0.1834 -0.0600 0.227 Uiso 1 1 calc R . . H18C H 1.3886 0.1480 0.0386 0.227 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 0.109(2) 0.104(2) 0.081(2) -0.0413(19) 0.0041(16) -0.0167(19) O2 0.082(2) 0.128(3) 0.116(3) -0.032(2) 0.0376(17) -0.048(2) C1 0.0553(19) 0.055(2) 0.054(2) -0.0052(16) -0.0055(15) -0.0201(16) C2 0.0549(19) 0.054(2) 0.053(2) -0.0056(16) -0.0058(15) -0.0243(16) C3 0.066(2) 0.064(2) 0.058(2) -0.0031(18) -0.0057(17) -0.0228(19) C4 0.083(3) 0.066(2) 0.060(2) 0.0031(19) -0.0143(19) -0.027(2) C5 0.071(2) 0.059(2) 0.075(3) 0.005(2) -0.020(2) -0.0161(19) C6 0.056(2) 0.061(2) 0.071(2) -0.0053(19) -0.0056(17) -0.0183(17) C7 0.0522(18) 0.0511(19) 0.059(2) -0.0053(16) -0.0056(15) -0.0209(15) C8 0.0495(18) 0.066(2) 0.055(2) -0.0107(17) 0.0010(14) -0.0233(17) C9 0.0550(18) 0.057(2) 0.0530(19) -0.0054(16) -0.0048(15) -0.0275(16) C10 0.067(2) 0.079(3) 0.050(2) 0.0007(18) -0.0059(17) -0.035(2) C12 0.082(3) 0.067(2) 0.059(2) 0.0068(19) -0.016(2) -0.020(2) C13 0.061(2) 0.065(2) 0.061(2) -0.0077(18) -0.0064(17) -0.0163(18) C14 0.0577(19) 0.052(2) 0.055(2) -0.0061(16) -0.0068(16) -0.0229(16) C15 0.065(2) 0.063(2) 0.063(2) 0.0020(19) 0.0004(18) -0.0134(19) C11 0.091(3) 0.085(3) 0.056(2) 0.012(2) -0.020(2) -0.039(2) C16 0.112(4) 0.128(5) 0.158(6) -0.014(4) 0.080(4) -0.037(4) C17 0.195(7) 0.153(6) 0.232(8) -0.093(6) 0.146(6) -0.120(6) C18 0.128(5) 0.162(6) 0.165(6) -0.067(5) 0.073(4) -0.089(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.178(4) . ? O2 C15 1.330(4) . ? O2 C16 1.469(5) . ? C1 C2 1.407(5) . ? C1 C14 1.409(4) . ? C1 C15 1.493(5) . ? C2 C3 1.429(4) . ? C2 C7 1.435(4) . ? C3 C4 1.344(5) . ? C3 H3 0.9300 . ? C4 C5 1.406(5) . ? C4 H4 0.9300 . ? C5 C6 1.350(5) . ? C5 H5 0.9300 . ? C6 C7 1.416(5) . ? C6 H6 0.9300 . ? C7 C8 1.397(4) . ? C8 C9 1.384(5) . ? C8 H8 0.9300 . ? C9 C10 1.426(4) . ? C9 C14 1.433(4) . ? C10 C11 1.351(5) . ? C10 H10 0.9300 . ? C12 C13 1.351(5) . ? C12 C11 1.409(5) . ? C12 H12 0.9300 . ? C13 C14 1.418(5) . ? C13 H13 0.9300 . ? C11 H11 0.9300 . ? C16 C17 1.234(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C15 O2 C16 117.4(4) . . ? C2 C1 C14 121.6(3) . . ? C2 C1 C15 118.4(3) . . ? C14 C1 C15 120.0(3) . . ? C1 C2 C3 123.4(3) . . ? C1 C2 C7 119.0(3) . . ? C3 C2 C7 117.6(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 121.9(3) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C8 C7 C6 122.9(3) . . ? C8 C7 C2 118.7(3) . . ? C6 C7 C2 118.4(3) . . ? C9 C8 C7 122.7(3) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C8 C9 C10 122.5(3) . . ? C8 C9 C14 119.3(3) . . ? C10 C9 C14 118.2(3) . . ? C11 C10 C9 121.2(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C1 C14 C13 123.0(3) . . ? C1 C14 C9 118.7(3) . . ? C13 C14 C9 118.3(3) . . ? O1 C15 O2 122.6(4) . . ? O1 C15 C1 126.3(4) . . ? O2 C15 C1 111.1(3) . . ? C10 C11 C12 120.4(4) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C17 C16 O2 116.2(5) . . ? C17 C16 H16A 108.2 . . ? O2 C16 H16A 108.2 . . ? C17 C16 H16B 108.2 . . ? O2 C16 H16B 108.2 . . ? H16A C16 H16B 107.4 . . ? C16 C17 C18 119.5(5) . . ? C16 C17 H17A 107.5 . . ? C18 C17 H17A 107.5 . . ? C16 C17 H17B 107.5 . . ? C18 C17 H17B 107.5 . . ? H17A C17 H17B 107.0 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.286 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.049 data_(4b) _database_code_depnum_ccdc_archive 'CCDC 812118' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Isopropyl anthracene-9-carboxylate' ; _chemical_name_common 'Isopropyl anthracene-9-carboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 O2' _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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 26.690(5) _cell_length_b 7.591(1) _cell_length_c 16.814(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.01(3) _cell_angle_gamma 90.00 _cell_volume 2888.6(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10083 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 24.99 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.078 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10083 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2476 _reflns_number_gt 1597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0887P)^2^+0.5977P] 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 2476 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1689 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.06984(8) 0.2469(2) 0.00528(14) 0.0962(7) Uani 1 1 d . . . O2 O 0.10393(7) 0.46950(17) -0.03809(12) 0.0742(5) Uani 1 1 d . . . C1 C 0.14818(9) 0.1944(2) -0.02034(15) 0.0557(5) Uani 1 1 d . . . C2 C 0.13515(9) 0.1241(2) -0.10625(16) 0.0584(6) Uani 1 1 d . . . C3 C 0.08075(11) 0.1542(3) -0.19253(18) 0.0711(6) Uani 1 1 d . . . H3 H 0.0523 0.2257 -0.1929 0.085 Uiso 1 1 calc R . . C4 C 0.06950(12) 0.0817(3) -0.27337(19) 0.0840(7) Uani 1 1 d . . . H4 H 0.0334 0.1032 -0.3283 0.101 Uiso 1 1 calc R . . C5 C 0.11122(15) -0.0256(3) -0.2765(2) 0.0888(8) Uani 1 1 d . . . H5 H 0.1029 -0.0743 -0.3330 0.107 Uiso 1 1 calc R . . C6 C 0.16353(14) -0.0576(3) -0.1967(2) 0.0813(8) Uani 1 1 d . . . H6 H 0.1909 -0.1293 -0.1992 0.098 Uiso 1 1 calc R . . C7 C 0.17810(11) 0.0148(2) -0.10875(18) 0.0645(6) Uani 1 1 d . . . C8 C 0.23149(11) -0.0158(3) -0.0266(2) 0.0727(7) Uani 1 1 d . . . H8 H 0.2594 -0.0857 -0.0285 0.087 Uiso 1 1 calc R . . C9 C 0.24494(10) 0.0543(3) 0.05918(19) 0.0685(6) Uani 1 1 d . . . C10 C 0.30068(12) 0.0258(3) 0.1438(2) 0.0856(8) Uani 1 1 d . . . H10 H 0.3290 -0.0431 0.1425 0.103 Uiso 1 1 calc R . . C11 C 0.31269(13) 0.0969(4) 0.2251(2) 0.0978(9) Uani 1 1 d . . . H11 H 0.3492 0.0763 0.2795 0.117 Uiso 1 1 calc R . . C12 C 0.27038(13) 0.2034(4) 0.2291(2) 0.0918(8) Uani 1 1 d . . . H12 H 0.2793 0.2522 0.2860 0.110 Uiso 1 1 calc R . . C13 C 0.21725(11) 0.2340(3) 0.15085(18) 0.0737(7) Uani 1 1 d . . . H13 H 0.1899 0.3037 0.1545 0.088 Uiso 1 1 calc R . . C14 C 0.20222(9) 0.1617(2) 0.06264(16) 0.0598(6) Uani 1 1 d . . . C15 C 0.10286(9) 0.3035(2) -0.01615(14) 0.0582(6) Uani 1 1 d . . . C16 C 0.06235(12) 0.5921(3) -0.03572(19) 0.0763(7) Uani 1 1 d . . . H16 H 0.0577 0.5569 0.0160 0.092 Uiso 1 1 calc R . . C17 C 0.00449(17) 0.5801(5) -0.1226(3) 0.1426(14) Uani 1 1 d . . . H17A H 0.0071 0.6245 -0.1737 0.214 Uiso 1 1 calc R . . H17B H -0.0236 0.6488 -0.1168 0.214 Uiso 1 1 calc R . . H17C H -0.0080 0.4594 -0.1344 0.214 Uiso 1 1 calc R . . C18 C 0.09098(18) 0.7681(4) -0.0129(3) 0.1598(18) Uani 1 1 d . . . H18A H 0.1308 0.7581 0.0397 0.240 Uiso 1 1 calc R . . H18B H 0.0693 0.8475 0.0025 0.240 Uiso 1 1 calc R . . H18C H 0.0913 0.8127 -0.0660 0.240 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 0.1195(15) 0.0679(11) 0.1630(18) 0.0235(10) 0.1168(15) 0.0172(9) O2 0.0895(11) 0.0477(8) 0.1159(13) 0.0149(7) 0.0750(11) 0.0117(7) C1 0.0614(13) 0.0428(10) 0.0783(15) 0.0054(9) 0.0476(13) -0.0001(8) C2 0.0644(14) 0.0455(11) 0.0807(16) 0.0008(9) 0.0489(13) -0.0009(9) C3 0.0700(16) 0.0688(14) 0.0881(18) -0.0089(12) 0.0511(15) -0.0030(11) C4 0.0847(18) 0.0900(17) 0.0860(19) -0.0187(14) 0.0511(16) -0.0121(13) C5 0.105(2) 0.0844(17) 0.101(2) -0.0290(15) 0.071(2) -0.0224(15) C6 0.103(2) 0.0575(13) 0.123(2) -0.0128(13) 0.087(2) -0.0033(12) C7 0.0757(16) 0.0449(11) 0.0977(18) 0.0014(10) 0.0627(15) 0.0005(10) C8 0.0801(18) 0.0474(12) 0.120(2) 0.0130(12) 0.0734(18) 0.0113(10) C9 0.0652(15) 0.0522(12) 0.1002(19) 0.0227(11) 0.0520(15) 0.0048(10) C10 0.0743(18) 0.0782(16) 0.114(2) 0.0380(16) 0.0563(18) 0.0114(12) C11 0.0698(18) 0.115(2) 0.099(2) 0.0443(18) 0.0384(17) -0.0008(15) C12 0.0817(19) 0.112(2) 0.085(2) 0.0152(15) 0.0463(18) -0.0165(16) C13 0.0726(16) 0.0771(14) 0.0816(18) 0.0102(12) 0.0478(15) -0.0051(12) C14 0.0646(14) 0.0494(11) 0.0795(16) 0.0119(10) 0.0477(13) -0.0020(9) C15 0.0680(14) 0.0503(11) 0.0711(14) 0.0033(9) 0.0468(12) 0.0025(9) C16 0.0942(19) 0.0575(13) 0.0990(19) 0.0100(11) 0.0660(17) 0.0204(12) C17 0.127(3) 0.155(3) 0.131(3) -0.003(2) 0.058(3) 0.064(2) C18 0.167(4) 0.0548(18) 0.272(6) -0.010(2) 0.126(4) 0.0063(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.195(2) . ? O2 C15 1.318(2) . ? O2 C16 1.465(2) . ? C1 C14 1.398(3) . ? C1 C2 1.400(3) . ? C1 C15 1.498(3) . ? C2 C3 1.426(3) . ? C2 C7 1.434(3) . ? C3 C4 1.344(3) . ? C3 H3 0.9300 . ? C4 C5 1.403(4) . ? C4 H4 0.9300 . ? C5 C6 1.350(4) . ? C5 H5 0.9300 . ? C6 C7 1.424(4) . ? C6 H6 0.9300 . ? C7 C8 1.381(3) . ? C8 C9 1.393(3) . ? C8 H8 0.9300 . ? C9 C14 1.428(3) . ? C9 C10 1.428(4) . ? C10 C11 1.341(4) . ? C10 H10 0.9300 . ? C11 C12 1.419(4) . ? C11 H11 0.9300 . ? C12 C13 1.349(3) . ? C12 H12 0.9300 . ? C13 C14 1.425(3) . ? C13 H13 0.9300 . ? C16 C17 1.461(4) . ? C16 C18 1.485(4) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C15 O2 C16 118.09(16) . . ? C14 C1 C2 121.51(19) . . ? C14 C1 C15 118.85(18) . . ? C2 C1 C15 119.62(19) . . ? C1 C2 C3 123.41(19) . . ? C1 C2 C7 119.1(2) . . ? C3 C2 C7 117.5(2) . . ? C4 C3 C2 121.6(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 122.1(2) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C8 C7 C6 122.9(2) . . ? C8 C7 C2 119.0(2) . . ? C6 C7 C2 118.1(2) . . ? C7 C8 C9 122.3(2) . . ? C7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C8 C9 C14 119.1(2) . . ? C8 C9 C10 122.3(2) . . ? C14 C9 C10 118.6(2) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 121.3(2) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C1 C14 C13 122.9(2) . . ? C1 C14 C9 119.0(2) . . ? C13 C14 C9 118.2(2) . . ? O1 C15 O2 123.83(18) . . ? O1 C15 C1 123.98(17) . . ? O2 C15 C1 112.19(16) . . ? C17 C16 O2 110.3(2) . . ? C17 C16 C18 116.1(3) . . ? O2 C16 C18 106.6(2) . . ? C17 C16 H16 107.8 . . ? O2 C16 H16 107.8 . . ? C18 C16 H16 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.9 _refine_diff_density_max 0.258 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.029 data_(4d) _database_code_depnum_ccdc_archive 'CCDC 812119' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-carbopropoxy-anthracene dimer ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H32 O4' _chemical_formula_sum 'C36 H32 O4' _chemical_formula_weight 528.60 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.496(2) _cell_length_b 9.220(2) _cell_length_c 10.151(3) _cell_angle_alpha 85.09(2) _cell_angle_beta 70.74(2) _cell_angle_gamma 69.22(2) _cell_volume 701.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7309 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.05 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.080 _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7309 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2468 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2468 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _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 0.68425(17) 0.34186(17) 0.79714(13) 0.0546(4) Uani 1 1 d . . . O2 O 0.84923(15) 0.40438(14) 0.89882(11) 0.0404(3) Uani 1 1 d . . . C1 C 0.9100(2) 0.44795(18) 0.65738(16) 0.0289(4) Uani 1 1 d . . . C2 C 1.1091(2) 0.35424(18) 0.62701(16) 0.0304(4) Uani 1 1 d . . . C3 C 1.1743(2) 0.2117(2) 0.68352(19) 0.0401(4) Uani 1 1 d . . . H3 H 1.0957 0.1676 0.7436 0.048 Uiso 1 1 d R . . C4 C 1.3554(2) 0.1349(2) 0.6511(2) 0.0491(5) Uani 1 1 d . . . H4 H 1.3980 0.0399 0.6900 0.059 Uiso 1 1 d R . . C5 C 1.4728(2) 0.1986(2) 0.5613(2) 0.0498(5) Uani 1 1 d . . . H5 H 1.5946 0.1474 0.5411 0.060 Uiso 1 1 d R . . C6 C 1.4101(2) 0.3378(2) 0.50172(19) 0.0397(4) Uani 1 1 d . . . H6 H 1.4899 0.3791 0.4393 0.048 Uiso 1 1 d R . . C7 C 1.2281(2) 0.41702(19) 0.53391(16) 0.0307(4) Uani 1 1 d . . . C8 C 1.1534(2) 0.57074(19) 0.47176(16) 0.0318(4) Uani 1 1 d . . . H8 H 1.2448 0.6141 0.4325 0.038 Uiso 1 1 d R . . C9 C 1.0053(2) 0.67773(19) 0.58756(16) 0.0316(4) Uani 1 1 d . . . C10 C 0.9886(2) 0.8312(2) 0.60353(18) 0.0400(4) Uani 1 1 d . . . H10 H 1.0726 0.8697 0.5432 0.048 Uiso 1 1 d R . . C11 C 0.8483(3) 0.9273(2) 0.7082(2) 0.0491(5) Uani 1 1 d . . . H11 H 0.8379 1.0299 0.7183 0.059 Uiso 1 1 d R . . C12 C 0.7242(3) 0.8702(2) 0.7977(2) 0.0494(5) Uani 1 1 d . . . H12 H 0.6283 0.9352 0.8670 0.059 Uiso 1 1 d R . . C13 C 0.7410(2) 0.7167(2) 0.78480(18) 0.0408(4) Uani 1 1 d . . . H13 H 0.6572 0.6788 0.8464 0.049 Uiso 1 1 d R . . C14 C 0.8819(2) 0.61872(18) 0.68077(16) 0.0302(4) Uani 1 1 d . . . C15 C 0.8002(2) 0.39067(19) 0.78980(17) 0.0334(4) Uani 1 1 d . . . C16 C 0.7490(2) 0.3700(2) 1.03782(17) 0.0468(5) Uani 1 1 d . . . H16 H 0.6230 0.4027 1.0460 0.056 Uiso 1 1 calc R . . C17 C 0.7712(3) 0.4659(3) 1.1368(2) 0.0782(8) Uani 1 1 d . . . H17A H 0.7191 0.5739 1.1205 0.094 Uiso 1 1 d R . . H17B H 0.8957 0.4409 1.1216 0.094 Uiso 1 1 d R . . H17C H 0.7139 0.4448 1.2313 0.094 Uiso 1 1 d R . . C18 C 0.8171(4) 0.1996(3) 1.0605(3) 0.1004(10) Uani 1 1 d . . . H18A H 0.7894 0.1448 1.0000 0.120 Uiso 1 1 d R . . H18B H 0.7629 0.1792 1.1559 0.120 Uiso 1 1 d R . . H18C H 0.9437 0.1654 1.0397 0.120 Uiso 1 1 d 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 0.0618(9) 0.0812(11) 0.0406(8) 0.0106(7) -0.0170(7) -0.0491(8) O2 0.0421(7) 0.0583(9) 0.0261(6) 0.0069(5) -0.0108(5) -0.0248(6) C1 0.0317(8) 0.0304(9) 0.0251(9) 0.0011(7) -0.0094(7) -0.0110(7) C2 0.0331(8) 0.0328(9) 0.0261(8) -0.0021(7) -0.0116(7) -0.0101(7) C3 0.0451(10) 0.0352(10) 0.0398(10) 0.0036(8) -0.0162(8) -0.0119(8) C4 0.0477(11) 0.0372(11) 0.0570(13) 0.0052(9) -0.0244(10) -0.0022(9) C5 0.0345(9) 0.0467(12) 0.0622(13) -0.0020(10) -0.0192(9) -0.0027(9) C6 0.0324(9) 0.0460(11) 0.0399(10) -0.0038(8) -0.0105(8) -0.0126(8) C7 0.0324(8) 0.0341(9) 0.0272(9) -0.0037(7) -0.0117(7) -0.0103(7) C8 0.0342(8) 0.0364(10) 0.0290(9) 0.0022(7) -0.0117(7) -0.0159(7) C9 0.0381(9) 0.0328(9) 0.0281(9) 0.0007(7) -0.0160(7) -0.0120(7) C10 0.0512(11) 0.0350(10) 0.0388(10) 0.0025(8) -0.0169(8) -0.0188(9) C11 0.0666(13) 0.0310(10) 0.0505(12) -0.0045(9) -0.0215(10) -0.0139(9) C12 0.0532(11) 0.0382(11) 0.0457(12) -0.0118(9) -0.0113(9) -0.0040(9) C13 0.0374(10) 0.0426(11) 0.0379(10) -0.0031(8) -0.0092(8) -0.0104(8) C14 0.0331(8) 0.0321(9) 0.0271(9) 0.0002(7) -0.0130(7) -0.0102(7) C15 0.0333(9) 0.0343(10) 0.0315(9) 0.0000(7) -0.0093(7) -0.0113(8) C16 0.0459(11) 0.0653(13) 0.0278(10) 0.0082(9) -0.0074(8) -0.0232(10) C17 0.0912(18) 0.124(2) 0.0324(12) -0.0053(13) -0.0110(12) -0.0586(17) C18 0.145(3) 0.079(2) 0.0668(18) 0.0330(15) -0.0322(18) -0.0341(19) _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 C15 1.200(2) . ? O2 C15 1.334(2) . ? O2 C16 1.463(2) . ? C1 C15 1.535(2) . ? C1 C14 1.534(2) . ? C1 C2 1.539(3) . ? C1 C8 1.615(2) 2_766 ? C2 C3 1.388(2) . ? C2 C7 1.394(2) . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9301 . ? C5 C6 1.375(3) . ? C5 H5 0.9300 . ? C6 C7 1.392(3) . ? C6 H6 0.9300 . ? C7 C8 1.511(2) . ? C8 C9 1.510(2) . ? C8 C1 1.615(2) 2_766 ? C8 H8 0.9546 . ? C9 C10 1.389(3) . ? C9 C14 1.398(2) . ? C10 C11 1.383(3) . ? C10 H10 0.9300 . ? C11 C12 1.376(3) . ? C11 H11 0.9300 . ? C12 C13 1.385(3) . ? C12 H12 0.9300 . ? C13 C14 1.388(2) . ? C13 H13 0.9300 . ? C16 C18 1.496(3) . ? C16 C17 1.491(3) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9599 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9601 . ? 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 C15 O2 C16 119.14(14) . . ? C15 C1 C14 109.20(13) . . ? C15 C1 C2 109.98(14) . . ? C14 C1 C2 107.80(12) . . ? C15 C1 C8 109.02(13) . 2_766 ? C14 C1 C8 110.30(12) . 2_766 ? C2 C1 C8 110.53(13) . 2_766 ? C3 C2 C7 119.29(15) . . ? C3 C2 C1 123.98(14) . . ? C7 C2 C1 116.71(15) . . ? C2 C3 C4 120.42(17) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.22(18) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.99(17) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 120.50(16) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 119.55(16) . . ? C6 C7 C8 122.28(15) . . ? C2 C7 C8 118.17(14) . . ? C9 C8 C7 108.02(13) . . ? C9 C8 C1 112.63(13) . 2_766 ? C7 C8 C1 112.40(13) . 2_766 ? C9 C8 H8 109.6 . . ? C7 C8 H8 109.3 . . ? C1 C8 H8 104.8 2_766 . ? C10 C9 C14 119.63(16) . . ? C10 C9 C8 122.20(16) . . ? C14 C9 C8 118.18(15) . . ? C11 C10 C9 120.66(17) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.66(18) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.35(18) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 120.58(17) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 119.09(16) . . ? C13 C14 C1 124.24(15) . . ? C9 C14 C1 116.65(14) . . ? O1 C15 O2 123.64(16) . . ? O1 C15 C1 125.71(15) . . ? O2 C15 C1 110.64(13) . . ? O2 C16 C18 109.99(18) . . ? O2 C16 C17 105.23(16) . . ? C18 C16 C17 113.4(2) . . ? O2 C16 H16 109.4 . . ? C18 C16 H16 109.4 . . ? C17 C16 H16 109.4 . . ? C16 C17 H17A 109.4 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.9 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.6 . . ? C16 C18 H18B 109.8 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.1 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.138 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.048 data_(I-3) _database_code_depnum_ccdc_archive 'CCDC 812120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol with 9-carbopropoxyanthracene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C18 H16 O2)' _chemical_formula_sum 'C66 H54 O6' _chemical_formula_weight 943.09 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.323(2) _cell_length_b 10.170(3) _cell_length_c 14.499(3) _cell_angle_alpha 109.54(2) _cell_angle_beta 98.57(3) _cell_angle_gamma 95.02(3) _cell_volume 1267.1(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12623 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _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 'Kappa CCD' _diffrn_measurement_method 'phi scan & omega scan' _diffrn_detector_area_resol_mean 95 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 12315 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4447 _reflns_number_gt 2561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.073(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4447 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 1.20066(13) 0.86070(13) 0.48010(10) 0.0588(4) Uani 1 1 d . . . H1 H 1.2441 0.8687 0.5356 0.107(10) Uiso 1 1 calc R . . O2 O 0.61771(15) 0.0762(2) 0.33492(11) 0.0962(6) Uani 1 1 d . . . O3 O 0.40788(13) 0.06841(15) 0.23663(10) 0.0707(4) Uani 1 1 d . . . C1 C 1.04019(17) 0.54428(19) 0.48258(13) 0.0487(4) Uani 1 1 d . . . C2 C 1.10895(17) 0.62123(19) 0.45236(13) 0.0492(5) Uani 1 1 d . . . C3 C 1.19040(16) 0.71779(18) 0.41382(13) 0.0456(4) Uani 1 1 d . . . C4 C 1.09742(16) 0.71260(19) 0.31502(13) 0.0489(5) Uani 1 1 d . . . C5 C 0.96522(19) 0.7657(2) 0.31813(16) 0.0684(6) Uani 1 1 d . . . H5 H 0.9356 0.8031 0.3789 0.086(7) Uiso 1 1 calc R . . C6 C 0.8771(2) 0.7636(3) 0.23180(18) 0.0844(7) Uani 1 1 d . . . H6 H 0.7885 0.7988 0.2348 0.106(8) Uiso 1 1 calc R . . C7 C 0.9202(2) 0.7096(3) 0.14179(18) 0.0846(7) Uani 1 1 d . . . H7 H 0.8608 0.7082 0.0838 0.108(8) Uiso 1 1 calc R . . C8 C 1.0511(2) 0.6575(3) 0.13735(16) 0.0781(7) Uani 1 1 d . . . H8 H 1.0806 0.6213 0.0764 0.085(7) Uiso 1 1 calc R . . C9 C 1.1397(2) 0.6590(2) 0.22386(15) 0.0621(5) Uani 1 1 d . . . H9 H 1.2281 0.6235 0.2204 0.059(5) Uiso 1 1 calc R . . C10 C 1.34264(16) 0.67645(19) 0.40164(12) 0.0476(4) Uani 1 1 d . . . C11 C 1.45526(18) 0.7789(2) 0.40604(16) 0.0652(6) Uani 1 1 d . . . H11 H 1.4381 0.8714 0.4188 0.086(7) Uiso 1 1 calc R . . C12 C 1.5928(2) 0.7443(3) 0.39162(17) 0.0785(7) Uani 1 1 d . . . H12 H 1.6670 0.8136 0.3943 0.096(7) Uiso 1 1 calc R . . C13 C 1.6200(2) 0.6083(3) 0.37336(18) 0.0815(7) Uani 1 1 d . . . H13 H 1.7122 0.5854 0.3634 0.087(7) Uiso 1 1 calc R . . C14 C 1.5107(2) 0.5064(3) 0.3699(2) 0.0878(8) Uani 1 1 d . . . H14 H 1.5289 0.4143 0.3581 0.107(9) Uiso 1 1 calc R . . C15 C 1.3721(2) 0.5410(2) 0.38395(17) 0.0700(6) Uani 1 1 d . . . H15 H 1.2984 0.4713 0.3813 0.093(7) Uiso 1 1 calc R . . C16 C 0.61261(17) 0.0130(2) 0.15997(13) 0.0525(5) Uani 1 1 d . . . C17 C 0.72674(17) 0.1062(2) 0.15115(14) 0.0534(5) Uani 1 1 d . . . C18 C 0.7838(2) 0.2418(2) 0.22546(16) 0.0673(6) Uani 1 1 d . . . H18 H 0.7463 0.2714 0.2838 0.075(7) Uiso 1 1 calc R . . C19 C 0.8928(2) 0.3282(3) 0.2115(2) 0.0807(7) Uani 1 1 d . . . H19 H 0.9281 0.4162 0.2603 0.098(8) Uiso 1 1 calc R . . C20 C 0.9527(2) 0.2855(3) 0.1240(2) 0.0825(7) Uani 1 1 d . . . H20 H 1.0282 0.3447 0.1163 0.107(8) Uiso 1 1 calc R . . C21 C 0.9014(2) 0.1600(3) 0.05174(18) 0.0720(6) Uani 1 1 d . . . H21 H 0.9407 0.1342 -0.0060 0.076(6) Uiso 1 1 calc R . . C22 C 0.78693(18) 0.0650(2) 0.06213(14) 0.0563(5) Uani 1 1 d . . . C23 C 0.7329(2) -0.0647(2) -0.01252(15) 0.0630(5) Uani 1 1 d . . . H23 H 0.7730 -0.0899 -0.0700 0.070(6) Uiso 1 1 calc R . . C24 C 0.62111(19) -0.1585(2) -0.00464(14) 0.0579(5) Uani 1 1 d . . . C25 C 0.5677(2) -0.2916(2) -0.08202(17) 0.0753(6) Uani 1 1 d . . . H25 H 0.6076 -0.3163 -0.1395 0.087(7) Uiso 1 1 calc R . . C26 C 0.4604(3) -0.3820(3) -0.0732(2) 0.0884(7) Uani 1 1 d . . . H26 H 0.4266 -0.4683 -0.1243 0.113(9) Uiso 1 1 calc R . . C27 C 0.3997(3) -0.3448(3) 0.0141(2) 0.0865(7) Uani 1 1 d . . . H27 H 0.3264 -0.4081 0.0199 0.109(8) Uiso 1 1 calc R . . C28 C 0.4455(2) -0.2189(2) 0.08991(19) 0.0718(6) Uani 1 1 d . . . H28 H 0.4031 -0.1976 0.1463 0.088(7) Uiso 1 1 calc R . . C29 C 0.55825(18) -0.1189(2) 0.08380(14) 0.0550(5) Uani 1 1 d . . . C30 C 0.5496(2) 0.0554(2) 0.25306(16) 0.0623(5) Uani 1 1 d . . . C31 C 0.3353(2) 0.1049(3) 0.32311(16) 0.0757(7) Uani 1 1 d . . . H31A H 0.3776 0.1985 0.3696 0.122(10) Uiso 1 1 calc R . . H31B H 0.3488 0.0382 0.3571 0.149(11) Uiso 1 1 calc R . . C32 C 0.1764(2) 0.1009(3) 0.28739(18) 0.0845(7) Uani 1 1 d . . . H32A H 0.1350 0.0070 0.2412 0.121(11) Uiso 1 1 calc R . . H32B H 0.1641 0.1663 0.2521 0.118(9) Uiso 1 1 calc R . . C33 C 0.0953(2) 0.1399(3) 0.37367(18) 0.0930(8) Uani 1 1 d . . . H33A H -0.0073 0.1338 0.3486 0.140 Uiso 1 1 calc R . . H33B H 0.1331 0.2346 0.4178 0.140 Uiso 1 1 calc R . . H33C H 0.1086 0.0762 0.4093 0.140 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 0.0627(7) 0.0562(9) 0.0575(9) 0.0217(7) 0.0059(6) 0.0102(6) O2 0.0745(9) 0.1587(17) 0.0556(10) 0.0400(10) 0.0059(8) 0.0204(9) O3 0.0646(8) 0.1035(12) 0.0576(9) 0.0376(8) 0.0196(6) 0.0323(7) C1 0.0483(9) 0.0572(12) 0.0475(11) 0.0251(9) 0.0131(8) 0.0101(8) C2 0.0478(9) 0.0598(12) 0.0471(11) 0.0261(10) 0.0117(8) 0.0116(8) C3 0.0470(9) 0.0470(11) 0.0457(11) 0.0216(9) 0.0072(8) 0.0037(7) C4 0.0434(9) 0.0595(12) 0.0516(11) 0.0321(10) 0.0074(8) -0.0001(8) C5 0.0529(11) 0.0986(17) 0.0673(14) 0.0450(13) 0.0128(10) 0.0162(10) C6 0.0551(12) 0.131(2) 0.0890(18) 0.0678(17) 0.0083(12) 0.0218(12) C7 0.0705(14) 0.118(2) 0.0767(17) 0.0618(16) -0.0077(12) 0.0015(13) C8 0.0827(14) 0.1033(19) 0.0546(14) 0.0401(13) 0.0079(11) 0.0066(13) C9 0.0576(11) 0.0769(15) 0.0569(13) 0.0318(11) 0.0083(9) 0.0077(10) C10 0.0441(9) 0.0585(12) 0.0463(11) 0.0270(9) 0.0076(7) 0.0054(8) C11 0.0501(11) 0.0710(16) 0.0837(15) 0.0388(12) 0.0162(9) 0.0052(9) C12 0.0509(12) 0.0876(18) 0.1028(19) 0.0408(15) 0.0206(11) 0.0012(11) C13 0.0529(12) 0.104(2) 0.0964(18) 0.0383(15) 0.0264(11) 0.0222(12) C14 0.0738(15) 0.0758(17) 0.129(2) 0.0417(16) 0.0417(14) 0.0305(12) C15 0.0595(11) 0.0590(14) 0.0992(18) 0.0328(13) 0.0253(11) 0.0116(10) C16 0.0489(9) 0.0625(13) 0.0497(11) 0.0238(10) 0.0059(8) 0.0160(9) C17 0.0503(10) 0.0620(13) 0.0505(12) 0.0237(10) 0.0037(8) 0.0169(9) C18 0.0670(12) 0.0679(15) 0.0618(14) 0.0200(12) 0.0025(11) 0.0106(11) C19 0.0752(14) 0.0691(17) 0.0871(18) 0.0246(15) -0.0037(13) 0.0000(12) C20 0.0688(13) 0.0909(19) 0.0937(19) 0.0470(17) 0.0068(13) -0.0002(13) C21 0.0634(12) 0.0909(18) 0.0724(16) 0.0413(14) 0.0163(11) 0.0111(12) C22 0.0523(10) 0.0667(14) 0.0537(12) 0.0265(11) 0.0052(9) 0.0153(9) C23 0.0619(11) 0.0841(16) 0.0500(12) 0.0292(12) 0.0111(10) 0.0243(11) C24 0.0608(11) 0.0612(13) 0.0506(12) 0.0198(10) 0.0011(9) 0.0199(9) C25 0.0878(15) 0.0705(16) 0.0590(15) 0.0149(12) 0.0003(12) 0.0223(13) C26 0.0947(17) 0.0597(17) 0.092(2) 0.0149(16) -0.0109(15) 0.0131(14) C27 0.0751(14) 0.0647(17) 0.117(2) 0.0356(17) 0.0030(14) 0.0053(12) C28 0.0637(12) 0.0664(16) 0.0876(17) 0.0301(14) 0.0137(12) 0.0109(11) C29 0.0511(10) 0.0574(13) 0.0596(13) 0.0263(11) 0.0021(9) 0.0148(9) C30 0.0603(12) 0.0743(15) 0.0570(14) 0.0287(11) 0.0097(10) 0.0144(10) C31 0.0814(14) 0.098(2) 0.0624(14) 0.0350(16) 0.0320(12) 0.0327(13) C32 0.0802(15) 0.114(2) 0.0761(16) 0.0407(18) 0.0333(12) 0.0398(14) C33 0.0857(15) 0.118(2) 0.0968(19) 0.0490(17) 0.0415(14) 0.0390(14) _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 C3 1.435(2) . ? O1 H1 0.8200 . ? O2 C30 1.200(2) . ? O3 C30 1.333(2) . ? O3 C31 1.467(2) . ? C1 C2 1.200(2) . ? C1 C1 1.388(3) 2_766 ? C2 C3 1.489(2) . ? C3 C10 1.534(2) . ? C3 C4 1.542(2) . ? C4 C9 1.382(2) . ? C4 C5 1.389(2) . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 C7 1.372(3) . ? C6 H6 0.9300 . ? C7 C8 1.374(3) . ? C7 H7 0.9300 . ? C8 C9 1.390(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.375(2) . ? C10 C11 1.391(2) . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 C13 1.372(3) . ? C12 H12 0.9300 . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C14 C15 1.394(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.411(2) . ? C16 C29 1.414(3) . ? C16 C30 1.498(3) . ? C17 C22 1.432(2) . ? C17 C18 1.433(3) . ? C18 C19 1.367(3) . ? C18 H18 0.9300 . ? C19 C20 1.413(3) . ? C19 H19 0.9300 . ? C20 C21 1.343(3) . ? C20 H20 0.9300 . ? C21 C22 1.435(3) . ? C21 H21 0.9300 . ? C22 C23 1.390(3) . ? C23 C24 1.395(3) . ? C23 H23 0.9300 . ? C24 C25 1.428(3) . ? C24 C29 1.439(3) . ? C25 C26 1.348(3) . ? C25 H25 0.9300 . ? C26 C27 1.413(3) . ? C26 H26 0.9300 . ? C27 C28 1.362(3) . ? C27 H27 0.9300 . ? C28 C29 1.431(3) . ? C28 H28 0.9300 . ? C31 C32 1.487(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.515(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 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 C3 O1 H1 109.5 . . ? C30 O3 C31 117.13(15) . . ? C2 C1 C1 179.6(2) . 2_766 ? C1 C2 C3 178.43(17) . . ? O1 C3 C2 109.50(14) . . ? O1 C3 C10 111.37(13) . . ? C2 C3 C10 110.16(14) . . ? O1 C3 C4 104.87(14) . . ? C2 C3 C4 108.25(13) . . ? C10 C3 C4 112.50(14) . . ? C9 C4 C5 118.49(17) . . ? C9 C4 C3 123.29(15) . . ? C5 C4 C3 118.21(16) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 120.58(19) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C15 C10 C11 118.25(17) . . ? C15 C10 C3 122.72(15) . . ? C11 C10 C3 119.02(17) . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.80(19) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 121.07(19) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C29 121.55(17) . . ? C17 C16 C30 118.70(18) . . ? C29 C16 C30 119.74(16) . . ? C16 C17 C22 118.49(18) . . ? C16 C17 C18 123.62(18) . . ? C22 C17 C18 117.87(17) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.8(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 121.1(2) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C23 C22 C17 119.69(17) . . ? C23 C22 C21 121.39(19) . . ? C17 C22 C21 118.92(19) . . ? C22 C23 C24 122.56(19) . . ? C22 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C23 C24 C25 121.7(2) . . ? C23 C24 C29 118.72(19) . . ? C25 C24 C29 119.61(19) . . ? C26 C25 C24 121.2(2) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.6(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 121.8(2) . . ? C28 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? C27 C28 C29 120.7(2) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C16 C29 C28 123.90(19) . . ? C16 C29 C24 118.99(17) . . ? C28 C29 C24 117.10(19) . . ? O2 C30 O3 122.36(19) . . ? O2 C30 C16 124.41(17) . . ? O3 C30 C16 113.23(16) . . ? O3 C31 C32 108.43(18) . . ? O3 C31 H31A 110.0 . . ? C32 C31 H31A 110.0 . . ? O3 C31 H31B 110.0 . . ? C32 C31 H31B 110.0 . . ? H31A C31 H31B 108.4 . . ? C31 C32 C33 111.0(2) . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 C1 C1 C2 C3 -12(45) 2_766 . . . ? C1 C2 C3 O1 78(7) . . . . ? C1 C2 C3 C10 -159(7) . . . . ? C1 C2 C3 C4 -36(7) . . . . ? O1 C3 C4 C9 129.14(17) . . . . ? C2 C3 C4 C9 -114.03(18) . . . . ? C10 C3 C4 C9 7.9(2) . . . . ? O1 C3 C4 C5 -50.28(19) . . . . ? C2 C3 C4 C5 66.5(2) . . . . ? C10 C3 C4 C5 -171.48(15) . . . . ? C9 C4 C5 C6 0.7(3) . . . . ? C3 C4 C5 C6 -179.88(18) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C5 C4 C9 C8 -0.4(3) . . . . ? C3 C4 C9 C8 -179.84(18) . . . . ? C7 C8 C9 C4 -0.1(3) . . . . ? O1 C3 C10 C15 149.05(18) . . . . ? C2 C3 C10 C15 27.3(2) . . . . ? C4 C3 C10 C15 -93.5(2) . . . . ? O1 C3 C10 C11 -32.6(2) . . . . ? C2 C3 C10 C11 -154.35(16) . . . . ? C4 C3 C10 C11 84.8(2) . . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C3 C10 C11 C12 -177.55(18) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C11 C10 C15 C14 -0.5(3) . . . . ? C3 C10 C15 C14 177.8(2) . . . . ? C13 C14 C15 C10 -0.2(4) . . . . ? C29 C16 C17 C22 0.5(2) . . . . ? C30 C16 C17 C22 179.82(15) . . . . ? C29 C16 C17 C18 178.93(16) . . . . ? C30 C16 C17 C18 -1.7(3) . . . . ? C16 C17 C18 C19 -178.83(17) . . . . ? C22 C17 C18 C19 -0.4(3) . . . . ? C17 C18 C19 C20 -0.5(3) . . . . ? C18 C19 C20 C21 1.3(3) . . . . ? C19 C20 C21 C22 -1.2(3) . . . . ? C16 C17 C22 C23 -0.4(2) . . . . ? C18 C17 C22 C23 -178.94(16) . . . . ? C16 C17 C22 C21 179.00(16) . . . . ? C18 C17 C22 C21 0.5(2) . . . . ? C20 C21 C22 C23 179.71(19) . . . . ? C20 C21 C22 C17 0.3(3) . . . . ? C17 C22 C23 C24 -0.1(3) . . . . ? C21 C22 C23 C24 -179.52(17) . . . . ? C22 C23 C24 C25 -179.69(17) . . . . ? C22 C23 C24 C29 0.6(3) . . . . ? C23 C24 C25 C26 179.39(19) . . . . ? C29 C24 C25 C26 -0.9(3) . . . . ? C24 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 C28 0.6(3) . . . . ? C26 C27 C28 C29 -0.1(3) . . . . ? C17 C16 C29 C28 178.32(16) . . . . ? C30 C16 C29 C28 -1.0(3) . . . . ? C17 C16 C29 C24 0.0(2) . . . . ? C30 C16 C29 C24 -179.37(15) . . . . ? C27 C28 C29 C16 -179.20(18) . . . . ? C27 C28 C29 C24 -0.8(3) . . . . ? C23 C24 C29 C16 -0.5(2) . . . . ? C25 C24 C29 C16 179.77(16) . . . . ? C23 C24 C29 C28 -178.96(16) . . . . ? C25 C24 C29 C28 1.3(2) . . . . ? C31 O3 C30 O2 -2.1(3) . . . . ? C31 O3 C30 C16 177.96(18) . . . . ? C17 C16 C30 O2 -62.4(3) . . . . ? C29 C16 C30 O2 117.0(2) . . . . ? C17 C16 C30 O3 117.58(18) . . . . ? C29 C16 C30 O3 -63.1(2) . . . . ? C30 O3 C31 C32 -174.8(2) . . . . ? O3 C31 C32 C33 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.137 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.029 data_(I-3d) _database_code_depnum_ccdc_archive 'CCDC 812121' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol with 9-carbopropoxyanthracene' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, C36 C32 O4' _chemical_formula_sum 'C66 H54 O6' _chemical_formula_weight 943.09 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.341(2) _cell_length_b 10.333(3) _cell_length_c 14.545(4) _cell_angle_alpha 109.68(2) _cell_angle_beta 99.28(3) _cell_angle_gamma 96.19(3) _cell_volume 1284.6(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10662 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _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 'Kappa CCD' _diffrn_measurement_method 'phi scan & omega scan' _diffrn_detector_area_resol_mean 95 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4183 _diffrn_reflns_av_R_equivalents 0.191 _diffrn_reflns_av_sigmaI/netI 0.1010 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4157 _reflns_number_gt 1569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2000)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _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^)+(0.0644P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4157 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2073 _refine_ls_R_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.2123 _refine_ls_wR_factor_gt 0.1876 _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_restrained_S_all 1.261 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 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 1.2060(3) 0.8584(3) 0.4829(3) 0.1006(10) Uani 1 1 d . . . H1 H 1.2498 0.8647 0.5383 0.12(2) Uiso 1 1 calc R . . O2 O 0.6140(5) 0.0797(5) 0.3305(3) 0.1523(17) Uani 1 1 d . . . O3 O 0.4022(5) 0.0748(4) 0.2371(2) 0.1195(12) Uani 1 1 d . . . C1 C 1.0401(5) 0.5454(5) 0.4832(3) 0.0881(13) Uani 1 1 d . . . C2 C 1.1086(5) 0.6216(5) 0.4528(3) 0.0874(14) Uani 1 1 d . . . C3 C 1.1889(4) 0.7175(5) 0.4146(3) 0.0783(12) Uani 1 1 d . . . C4 C 1.0924(5) 0.7132(5) 0.3146(3) 0.0838(13) Uani 1 1 d . . . C5 C 0.9652(6) 0.7671(6) 0.3198(5) 0.1183(18) Uani 1 1 d . . . H5 H 0.9378 0.8047 0.3808 0.13(2) Uiso 1 1 calc R . . C6 C 0.8780(7) 0.7647(7) 0.2324(6) 0.146(2) Uani 1 1 d . . . H6 H 0.7916 0.8016 0.2356 0.17(3) Uiso 1 1 calc R . . C7 C 0.9149(8) 0.7094(7) 0.1413(5) 0.136(2) Uani 1 1 d . . . H7 H 0.8541 0.7085 0.0837 0.19(3) Uiso 1 1 calc R . . C8 C 1.0398(8) 0.6566(7) 0.1361(5) 0.132(2) Uani 1 1 d . . . H8 H 1.0654 0.6201 0.0745 0.13(2) Uiso 1 1 calc R . . C9 C 1.1336(7) 0.6555(6) 0.2231(4) 0.1130(17) Uani 1 1 d . . . H9 H 1.2194 0.6177 0.2193 0.25(4) Uiso 1 1 calc R . . C10 C 1.3408(5) 0.6790(6) 0.4013(3) 0.0787(12) Uani 1 1 d . . . C11 C 1.4530(6) 0.7770(6) 0.4015(3) 0.1027(15) Uani 1 1 d . . . H11 H 1.4374 0.8679 0.4126 0.093(16) Uiso 1 1 calc R . . C12 C 1.5906(6) 0.7426(8) 0.3851(4) 0.1218(19) Uani 1 1 d . . . H12 H 1.6653 0.8099 0.3854 0.18(3) Uiso 1 1 calc R . . C13 C 1.6132(7) 0.6088(8) 0.3688(4) 0.1210(18) Uani 1 1 d . . . H13 H 1.7037 0.5851 0.3575 0.18(3) Uiso 1 1 calc R . . C14 C 1.5055(7) 0.5108(7) 0.3690(4) 0.1231(19) Uani 1 1 d . . . H14 H 1.5219 0.4202 0.3582 0.18(3) Uiso 1 1 calc R . . C15 C 1.3701(6) 0.5462(6) 0.3855(4) 0.1054(16) Uani 1 1 d . . . H15 H 1.2967 0.4780 0.3858 0.128(18) Uiso 1 1 calc R . . C16 C 0.6087(6) 0.0165(7) 0.1580(4) 0.091(2) Uani 0.821(7) 1 d P . . C17 C 0.7187(6) 0.1086(6) 0.1489(4) 0.1036(16) Uani 1 1 d . . . C18 C 0.7822(7) 0.2388(7) 0.2212(5) 0.1104(17) Uani 1 1 d . . . H18 H 0.7459 0.2721 0.2791 0.15(3) Uiso 1 1 calc R . . C19 C 0.8976(7) 0.3175(8) 0.2070(6) 0.133(2) Uani 1 1 d . . . H19 H 0.9409 0.4031 0.2566 0.13(2) Uiso 1 1 calc R . . C20 C 0.9537(9) 0.2715(10) 0.1178(6) 0.144(2) Uani 1 1 d . . . H20 H 1.0306 0.3282 0.1089 0.30(5) Uiso 1 1 calc R . . C21 C 0.8969(8) 0.1502(9) 0.0488(6) 0.130(2) Uani 1 1 d . . . H21 H 0.9357 0.1205 -0.0083 0.16(2) Uiso 1 1 calc R . . C22 C 0.7783(7) 0.0625(7) 0.0585(5) 0.1195(19) Uani 1 1 d . . . C23 C 0.7274(8) -0.0608(8) -0.0124(6) 0.115(3) Uani 0.821(7) 1 d P . . H23 H 0.7548 -0.0834 -0.0707 0.22(3) Uiso 1 1 d R . . C24 C 0.6070(7) -0.1613(6) -0.0065(4) 0.1080(18) Uani 1 1 d . . . C25 C 0.5570(8) -0.2924(8) -0.0771(5) 0.126(2) Uani 1 1 d . . . H25 H 0.5979 -0.3192 -0.1334 0.112(18) Uiso 1 1 calc R . . C26 C 0.4546(10) -0.3809(9) -0.0683(7) 0.171(3) Uani 1 1 d . . . H26 H 0.4194 -0.4672 -0.1192 0.22(4) Uiso 1 1 calc R . . C27 C 0.3962(8) -0.3430(9) 0.0219(7) 0.171(3) Uani 1 1 d . . . H27 H 0.3270 -0.4072 0.0307 0.16(2) Uiso 1 1 calc R . . C28 C 0.4418(6) -0.2151(7) 0.0929(5) 0.1165(17) Uani 1 1 d . . . H28 H 0.4034 -0.1923 0.1503 0.080(15) Uiso 1 1 calc R . . C29 C 0.5448(6) -0.1166(6) 0.0825(4) 0.0941(14) Uani 1 1 d . . . C30 C 0.5432(8) 0.0590(6) 0.2524(5) 0.1086(17) Uani 1 1 d . . . C31 C 0.3348(7) 0.1072(8) 0.3264(4) 0.1229(19) Uani 1 1 d . . . H31A H 0.3477 0.0384 0.3574 0.18(3) Uiso 1 1 calc R . . H31B H 0.3807 0.1986 0.3750 0.106(19) Uiso 1 1 calc R . . C32 C 0.1757(8) 0.1041(12) 0.2913(6) 0.156(2) Uani 1 1 d . . . H32A H 0.1303 0.0115 0.2444 0.22(4) Uiso 1 1 calc R . . H32B H 0.1642 0.1694 0.2570 0.35(7) Uiso 1 1 calc R . . C33 C 0.1007(6) 0.1420(6) 0.3776(4) 0.163(2) Uani 1 1 d . . . H33A H -0.0022 0.1382 0.3537 0.245 Uiso 1 1 calc R . . H33B H 0.1438 0.2348 0.4230 0.245 Uiso 1 1 calc R . . H33C H 0.1123 0.0774 0.4115 0.245 Uiso 1 1 calc R . . C231 C 0.5907(9) -0.0831(14) -0.0688(5) 0.064(7) Uiso 0.179(7) 1 d PR . . C161 C 0.4900(6) 0.0262(14) 0.1158(4) 0.063(7) Uiso 0.179(7) 1 d PR . . 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 0.110(2) 0.106(3) 0.099(2) 0.050(2) 0.027(2) 0.0261(18) O2 0.127(3) 0.230(5) 0.110(3) 0.067(3) 0.037(3) 0.037(3) O3 0.125(3) 0.176(3) 0.086(2) 0.075(2) 0.031(2) 0.040(3) C1 0.093(3) 0.111(4) 0.087(3) 0.058(3) 0.036(2) 0.028(3) C2 0.085(3) 0.123(4) 0.083(3) 0.063(3) 0.034(2) 0.027(3) C3 0.080(3) 0.092(3) 0.083(3) 0.054(3) 0.028(2) 0.013(3) C4 0.070(3) 0.115(4) 0.086(3) 0.068(3) 0.013(3) 0.001(3) C5 0.071(4) 0.204(6) 0.132(5) 0.116(4) 0.034(3) 0.043(4) C6 0.087(4) 0.230(7) 0.177(7) 0.135(6) 0.034(5) 0.042(4) C7 0.094(5) 0.218(7) 0.133(6) 0.113(5) 0.024(5) 0.017(4) C8 0.128(5) 0.188(6) 0.096(5) 0.079(4) 0.021(4) 0.015(5) C9 0.121(5) 0.149(5) 0.084(4) 0.065(3) 0.022(3) 0.008(4) C10 0.066(3) 0.105(4) 0.083(3) 0.056(3) 0.021(2) 0.008(3) C11 0.088(4) 0.112(5) 0.125(4) 0.065(3) 0.029(3) 0.006(3) C12 0.082(4) 0.158(6) 0.149(5) 0.074(4) 0.050(3) 0.017(4) C13 0.110(5) 0.148(6) 0.132(5) 0.066(4) 0.055(4) 0.044(5) C14 0.104(5) 0.128(5) 0.169(5) 0.072(4) 0.064(4) 0.036(4) C15 0.093(4) 0.115(4) 0.130(4) 0.061(3) 0.048(3) 0.016(4) C16 0.096(5) 0.105(5) 0.074(4) 0.031(4) 0.032(3) 0.010(4) C17 0.119(4) 0.112(4) 0.104(4) 0.052(4) 0.061(4) 0.028(4) C18 0.113(4) 0.111(5) 0.120(5) 0.055(4) 0.031(4) 0.022(4) C19 0.120(5) 0.143(6) 0.142(6) 0.072(5) 0.013(5) 0.003(5) C20 0.134(6) 0.201(8) 0.145(7) 0.100(6) 0.068(5) 0.057(6) C21 0.160(7) 0.146(6) 0.123(6) 0.071(5) 0.065(5) 0.056(5) C22 0.150(5) 0.117(5) 0.118(5) 0.065(4) 0.054(4) 0.021(4) C23 0.146(6) 0.122(6) 0.081(5) 0.046(4) 0.037(4) -0.002(5) C24 0.160(5) 0.109(4) 0.063(3) 0.032(3) 0.023(4) 0.049(4) C25 0.125(5) 0.140(6) 0.087(5) 0.014(4) 0.003(4) 0.026(4) C26 0.132(7) 0.140(7) 0.181(9) -0.003(7) 0.005(6) 0.016(5) C27 0.135(6) 0.143(6) 0.203(9) 0.030(6) 0.050(6) -0.020(6) C28 0.091(4) 0.122(5) 0.130(5) 0.040(4) 0.026(4) 0.004(4) C29 0.107(4) 0.099(4) 0.081(4) 0.041(3) 0.017(3) 0.019(3) C30 0.120(5) 0.120(4) 0.084(4) 0.031(3) 0.036(4) 0.008(4) C31 0.120(5) 0.169(6) 0.109(4) 0.071(5) 0.046(4) 0.045(5) C32 0.141(6) 0.223(9) 0.133(5) 0.074(7) 0.064(5) 0.074(6) C33 0.150(5) 0.194(6) 0.159(6) 0.062(5) 0.052(5) 0.057(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.434(4) . ? O1 H1 0.8200 . ? O2 C30 1.156(6) . ? O3 C30 1.336(6) . ? O3 C31 1.488(6) . ? C1 C2 1.200(5) . ? C1 C1 1.399(9) 2_766 ? C2 C3 1.482(6) . ? C3 C10 1.539(6) . ? C3 C4 1.568(5) . ? C4 C5 1.368(6) . ? C4 C9 1.398(6) . ? C5 C6 1.386(7) . ? C5 H5 0.9300 . ? C6 C7 1.371(7) . ? C6 H6 0.9300 . ? C7 C8 1.342(7) . ? C7 H7 0.9300 . ? C8 C9 1.423(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.375(5) . ? C10 C15 1.378(6) . ? C11 C12 1.405(6) . ? C11 H11 0.9300 . ? C12 C13 1.368(7) . ? C12 H12 0.9300 . ? C13 C14 1.349(7) . ? C13 H13 0.9300 . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C161 1.209(8) . ? C16 C17 1.377(7) . ? C16 C29 1.431(6) . ? C16 C30 1.541(7) . ? C17 C18 1.393(6) . ? C17 C22 1.463(7) . ? C18 C19 1.365(7) . ? C18 H18 0.9300 . ? C19 C20 1.429(8) . ? C19 H19 0.9300 . ? C20 C21 1.303(7) . ? C20 H20 0.9300 . ? C21 C22 1.409(7) . ? C21 H21 0.9300 . ? C22 C23 1.319(7) . ? C23 C231 1.352(9) . ? C23 C24 1.480(7) . ? C23 H23 0.8878 . ? C24 C25 1.370(7) . ? C24 C231 1.404(10) . ? C24 C29 1.458(6) . ? C25 C26 1.303(8) . ? C25 H25 0.9300 . ? C26 C27 1.451(9) . ? C26 H26 0.9300 . ? C27 C28 1.345(7) . ? C27 H27 0.9300 . ? C28 C29 1.388(6) . ? C28 H28 0.9300 . ? C29 C161 1.560(13) . ? C30 C161 1.871(9) . ? C31 C32 1.485(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.493(7) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C231 C161 1.257(15) 2_655 ? C231 H23 1.5384 . ? C161 C231 1.26(2) 2_655 ? 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 C3 O1 H1 109.5 . . ? C30 O3 C31 115.6(4) . . ? C2 C1 C1 178.9(6) . 2_766 ? C1 C2 C3 178.2(5) . . ? O1 C3 C2 109.5(4) . . ? O1 C3 C10 110.0(3) . . ? C2 C3 C10 110.5(4) . . ? O1 C3 C4 105.5(4) . . ? C2 C3 C4 109.2(3) . . ? C10 C3 C4 112.0(4) . . ? C5 C4 C9 121.0(5) . . ? C5 C4 C3 117.5(5) . . ? C9 C4 C3 121.5(5) . . ? C4 C5 C6 118.6(6) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 122.1(7) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C8 C7 C6 119.3(6) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 121.3(7) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C4 C9 C8 117.7(7) . . ? C4 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? C11 C10 C15 117.0(5) . . ? C11 C10 C3 120.5(5) . . ? C15 C10 C3 122.5(4) . . ? C10 C11 C12 121.4(6) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 119.2(6) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 120.7(7) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.6(6) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 122.2(5) . . ? C10 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C161 C16 C17 110.4(7) . . ? C161 C16 C29 71.9(7) . . ? C17 C16 C29 124.0(6) . . ? C161 C16 C30 84.9(5) . . ? C17 C16 C30 119.3(6) . . ? C29 C16 C30 116.6(5) . . ? C16 C17 C18 125.1(6) . . ? C16 C17 C22 117.1(6) . . ? C18 C17 C22 117.7(6) . . ? C19 C18 C17 120.0(7) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 121.6(8) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C21 C20 C19 119.9(8) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 121.8(8) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C23 C22 C21 119.3(7) . . ? C23 C22 C17 121.7(6) . . ? C21 C22 C17 119.0(6) . . ? C22 C23 C231 118.5(8) . . ? C22 C23 C24 122.8(7) . . ? C231 C23 C24 59.2(5) . . ? C22 C23 H23 121.2 . . ? C231 C23 H23 84.0 . . ? C24 C23 H23 115.5 . . ? C25 C24 C231 99.1(7) . . ? C25 C24 C29 119.8(6) . . ? C231 C24 C29 116.6(5) . . ? C25 C24 C23 123.8(7) . . ? C231 C24 C23 55.9(5) . . ? C29 C24 C23 116.4(6) . . ? C26 C25 C24 122.6(8) . . ? C26 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? C25 C26 C27 119.1(8) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 120.1(8) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 121.6(7) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C16 124.9(6) . . ? C28 C29 C24 116.6(6) . . ? C16 C29 C24 117.9(5) . . ? C28 C29 C161 107.8(6) . . ? C16 C29 C161 47.4(3) . . ? C24 C29 C161 120.6(5) . . ? O2 C30 O3 123.5(5) . . ? O2 C30 C16 121.5(6) . . ? O3 C30 C16 115.0(6) . . ? O2 C30 C161 161.0(6) . . ? O3 C30 C161 75.0(4) . . ? C16 C30 C161 40.0(3) . . ? C32 C31 O3 107.0(5) . . ? C32 C31 H31A 110.3 . . ? O3 C31 H31A 110.3 . . ? C32 C31 H31B 110.3 . . ? O3 C31 H31B 110.3 . . ? H31A C31 H31B 108.6 . . ? C31 C32 C33 110.4(6) . . ? C31 C32 H32A 109.6 . . ? C33 C32 H32A 109.6 . . ? C31 C32 H32B 109.6 . . ? C33 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C161 C231 C23 140.8(8) 2_655 . ? C161 C231 C24 149.6(8) 2_655 . ? C23 C231 C24 64.9(4) . . ? C161 C231 H23 123.4 2_655 . ? C23 C231 H23 35.0 . . ? C24 C231 H23 87.0 . . ? C16 C161 C231 151.8(10) . 2_655 ? C16 C161 C29 60.7(6) . . ? C231 C161 C29 132.3(7) 2_655 . ? C16 C161 C30 55.1(4) . . ? C231 C161 C30 131.4(8) 2_655 . ? C29 C161 C30 94.5(6) . . ? 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 C1 C1 C2 C3 98(36) 2_766 . . . ? C1 C2 C3 O1 70(16) . . . . ? C1 C2 C3 C10 -168(15) . . . . ? C1 C2 C3 C4 -45(16) . . . . ? O1 C3 C4 C5 -49.9(5) . . . . ? C2 C3 C4 C5 67.8(5) . . . . ? C10 C3 C4 C5 -169.5(4) . . . . ? O1 C3 C4 C9 130.7(4) . . . . ? C2 C3 C4 C9 -111.7(5) . . . . ? C10 C3 C4 C9 11.0(6) . . . . ? C9 C4 C5 C6 -0.6(7) . . . . ? C3 C4 C5 C6 -180.0(4) . . . . ? C4 C5 C6 C7 0.3(8) . . . . ? C5 C6 C7 C8 -0.4(9) . . . . ? C6 C7 C8 C9 0.7(9) . . . . ? C5 C4 C9 C8 0.8(7) . . . . ? C3 C4 C9 C8 -179.8(4) . . . . ? C7 C8 C9 C4 -0.9(8) . . . . ? O1 C3 C10 C11 -35.8(5) . . . . ? C2 C3 C10 C11 -156.9(4) . . . . ? C4 C3 C10 C11 81.2(5) . . . . ? O1 C3 C10 C15 146.5(4) . . . . ? C2 C3 C10 C15 25.4(5) . . . . ? C4 C3 C10 C15 -96.6(5) . . . . ? C15 C10 C11 C12 0.6(6) . . . . ? C3 C10 C11 C12 -177.2(4) . . . . ? C10 C11 C12 C13 0.0(8) . . . . ? C11 C12 C13 C14 -0.5(8) . . . . ? C12 C13 C14 C15 0.3(9) . . . . ? C11 C10 C15 C14 -0.8(7) . . . . ? C3 C10 C15 C14 177.0(4) . . . . ? C13 C14 C15 C10 0.3(8) . . . . ? C161 C16 C17 C18 98.3(8) . . . . ? C29 C16 C17 C18 179.8(5) . . . . ? C30 C16 C17 C18 2.6(9) . . . . ? C161 C16 C17 C22 -85.0(8) . . . . ? C29 C16 C17 C22 -3.6(8) . . . . ? C30 C16 C17 C22 179.3(5) . . . . ? C16 C17 C18 C19 175.5(5) . . . . ? C22 C17 C18 C19 -1.2(7) . . . . ? C17 C18 C19 C20 1.8(8) . . . . ? C18 C19 C20 C21 -1.9(9) . . . . ? C19 C20 C21 C22 1.3(10) . . . . ? C20 C21 C22 C23 -178.3(6) . . . . ? C20 C21 C22 C17 -0.8(9) . . . . ? C16 C17 C22 C23 1.2(8) . . . . ? C18 C17 C22 C23 178.1(6) . . . . ? C16 C17 C22 C21 -176.3(5) . . . . ? C18 C17 C22 C21 0.6(7) . . . . ? C21 C22 C23 C231 -112.4(8) . . . . ? C17 C22 C23 C231 70.2(9) . . . . ? C21 C22 C23 C24 177.7(5) . . . . ? C17 C22 C23 C24 0.2(9) . . . . ? C22 C23 C24 C25 -176.9(5) . . . . ? C231 C23 C24 C25 77.0(7) . . . . ? C22 C23 C24 C231 106.1(9) . . . . ? C22 C23 C24 C29 0.6(8) . . . . ? C231 C23 C24 C29 -105.5(6) . . . . ? C231 C24 C25 C26 -127.9(7) . . . . ? C29 C24 C25 C26 -0.1(9) . . . . ? C23 C24 C25 C26 177.3(6) . . . . ? C24 C25 C26 C27 -3.5(11) . . . . ? C25 C26 C27 C28 3.6(11) . . . . ? C26 C27 C28 C29 0.0(10) . . . . ? C27 C28 C29 C16 -174.1(5) . . . . ? C27 C28 C29 C24 -3.4(8) . . . . ? C27 C28 C29 C161 135.9(6) . . . . ? C161 C16 C29 C28 -82.2(7) . . . . ? C17 C16 C29 C28 175.0(5) . . . . ? C30 C16 C29 C28 -7.8(8) . . . . ? C161 C16 C29 C24 107.2(6) . . . . ? C17 C16 C29 C24 4.4(7) . . . . ? C30 C16 C29 C24 -178.4(5) . . . . ? C17 C16 C29 C161 -102.9(7) . . . . ? C30 C16 C29 C161 74.4(7) . . . . ? C25 C24 C29 C28 3.5(7) . . . . ? C231 C24 C29 C28 122.8(8) . . . . ? C23 C24 C29 C28 -174.1(5) . . . . ? C25 C24 C29 C16 174.9(5) . . . . ? C231 C24 C29 C16 -65.8(8) . . . . ? C23 C24 C29 C16 -2.7(6) . . . . ? C25 C24 C29 C161 -130.3(6) . . . . ? C231 C24 C29 C161 -11.0(8) . . . . ? C23 C24 C29 C161 52.1(7) . . . . ? C31 O3 C30 O2 -6.1(9) . . . . ? C31 O3 C30 C16 176.4(5) . . . . ? C31 O3 C30 C161 178.4(6) . . . . ? C161 C16 C30 O2 -174.5(9) . . . . ? C17 C16 C30 O2 -63.9(8) . . . . ? C29 C16 C30 O2 118.7(6) . . . . ? C161 C16 C30 O3 3.1(9) . . . . ? C17 C16 C30 O3 113.6(6) . . . . ? C29 C16 C30 O3 -63.7(7) . . . . ? C17 C16 C30 C161 110.6(9) . . . . ? C29 C16 C30 C161 -66.8(8) . . . . ? C30 O3 C31 C32 -173.6(6) . . . . ? O3 C31 C32 C33 -177.5(6) . . . . ? C22 C23 C231 C161 45.8(16) . . . 2_655 ? C24 C23 C231 C161 159.0(14) . . . 2_655 ? C22 C23 C231 C24 -113.2(8) . . . . ? C25 C24 C231 C161 81.6(16) . . . 2_655 ? C29 C24 C231 C161 -48.3(18) . . . 2_655 ? C23 C24 C231 C161 -153.5(17) . . . 2_655 ? C25 C24 C231 C23 -124.9(7) . . . . ? C29 C24 C231 C23 105.1(7) . . . . ? C17 C16 C161 C231 -6(2) . . . 2_655 ? C29 C16 C161 C231 -125.9(19) . . . 2_655 ? C30 C16 C161 C231 113.9(18) . . . 2_655 ? C17 C16 C161 C29 120.4(6) . . . . ? C30 C16 C161 C29 -120.2(5) . . . . ? C17 C16 C161 C30 -119.4(7) . . . . ? C29 C16 C161 C30 120.2(5) . . . . ? C28 C29 C161 C16 121.5(6) . . . . ? C24 C29 C161 C16 -101.2(6) . . . . ? C28 C29 C161 C231 -89.7(10) . . . 2_655 ? C16 C29 C161 C231 148.9(12) . . . 2_655 ? C24 C29 C161 C231 47.7(12) . . . 2_655 ? C28 C29 C161 C30 76.1(5) . . . . ? C16 C29 C161 C30 -45.4(4) . . . . ? C24 C29 C161 C30 -146.5(5) . . . . ? O2 C30 C161 C16 15(2) . . . . ? O3 C30 C161 C16 -177.1(8) . . . . ? O2 C30 C161 C231 -130.3(19) . . . 2_655 ? O3 C30 C161 C231 38.0(9) . . . 2_655 ? C16 C30 C161 C231 -144.9(13) . . . 2_655 ? O2 C30 C161 C29 64(2) . . . . ? O3 C30 C161 C29 -128.0(5) . . . . ? C16 C30 C161 C29 49.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.200 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.036