# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Masami Sakamoto' _publ_contact_author_email SAKAMOTOM@FACULTY.CHIBA-U.JP _publ_section_title ; Photodimerization of Chromone ; _publ_contact_author_address ; Department of Applied Chemistry and Biotechnology, Chiba University ; loop_ _publ_author_name 'Masami Sakamoto' 'Masayuki Kanehiro' 'Takashi Mino' 'Tsutomu Fujita' # Attachment 'cis_Chromone_Dimer2.cif.txt' data_saka91b_c2c _database_code_depnum_ccdc_archive 'CCDC 714210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 O4' _chemical_formula_weight 292.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.8002(10) _cell_length_b 8.2800(6) _cell_length_c 22.2830(19) _cell_angle_alpha 90.00 _cell_angle_beta 103.7710(10) _cell_angle_gamma 90.00 _cell_volume 2652.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173 _cell_measurement_reflns_used 2242 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.32 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 7287 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3007 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.8038P] 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 3007 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.03408(8) 0.54530(12) 0.13421(5) 0.0297(3) Uani 1 1 d . . . C9 C 0.12042(10) 1.06127(16) 0.24779(6) 0.0223(3) Uani 1 1 d . . . C13 C 0.10876(10) 0.59585(16) 0.04940(6) 0.0227(3) Uani 1 1 d . . . C11 C 0.06343(10) 0.83768(16) 0.10603(6) 0.0234(3) Uani 1 1 d . . . H11 H 0.0081 0.9086 0.0903 0.028 Uiso 1 1 calc R . . C10 C 0.04797(10) 0.70901(16) 0.15281(6) 0.0241(3) Uani 1 1 d . . . H10 H -0.0028 0.7447 0.1724 0.029 Uiso 1 1 calc R . . C5 C 0.16611(11) 0.96017(18) 0.35188(6) 0.0283(3) Uani 1 1 d . . . H5 H 0.1861 0.8738 0.3800 0.034 Uiso 1 1 calc R . . C4 C 0.14803(10) 0.93124(17) 0.28801(6) 0.0232(3) Uani 1 1 d . . . C3 C 0.15486(10) 0.76693(17) 0.26369(6) 0.0249(3) Uani 1 1 d . . . C2 C 0.14416(10) 0.75558(16) 0.19496(6) 0.0219(3) Uani 1 1 d . . . H2 H 0.1939 0.6850 0.1857 0.026 Uiso 1 1 calc R . . C8 C 0.11160(10) 1.21588(17) 0.27028(6) 0.0257(3) Uani 1 1 d . . . H8 H 0.0945 1.3039 0.2426 0.031 Uiso 1 1 calc R . . C17 C 0.07819(11) 0.32648(18) 0.08119(7) 0.0328(4) Uani 1 1 d . . . H17 H 0.0551 0.2566 0.1079 0.039 Uiso 1 1 calc R . . C14 C 0.14623(11) 0.52868(18) 0.00274(7) 0.0279(3) Uani 1 1 d . . . H14 H 0.1699 0.5976 -0.0240 0.033 Uiso 1 1 calc R . . C1 C 0.13815(10) 0.91498(16) 0.15848(6) 0.0232(3) Uani 1 1 d . . . H1 H 0.1968 0.9461 0.1465 0.028 Uiso 1 1 calc R . . C18 C 0.07468(10) 0.49292(17) 0.08847(6) 0.0245(3) Uani 1 1 d . . . C12 C 0.10550(10) 0.77169(17) 0.05560(6) 0.0247(3) Uani 1 1 d . . . C7 C 0.12792(10) 1.24004(19) 0.33336(7) 0.0295(3) Uani 1 1 d . . . H7 H 0.1204 1.3448 0.3489 0.035 Uiso 1 1 calc R . . C15 C 0.14900(12) 0.36403(19) -0.00455(7) 0.0346(4) Uani 1 1 d . . . H15 H 0.1738 0.3192 -0.0365 0.041 Uiso 1 1 calc R . . C6 C 0.15530(11) 1.1122(2) 0.37435(7) 0.0318(4) Uani 1 1 d . . . H6 H 0.1665 1.1298 0.4176 0.038 Uiso 1 1 calc R . . C16 C 0.11523(12) 0.26340(18) 0.03516(8) 0.0371(4) Uani 1 1 d . . . H16 H 0.1178 0.1496 0.0304 0.045 Uiso 1 1 calc R . . O4 O 0.13552(10) 0.86414(13) 0.02237(5) 0.0427(3) Uani 1 1 d . . . O1 O 0.09520(8) 1.04309(11) 0.18488(4) 0.0281(3) Uani 1 1 d . . . O2 O 0.16601(9) 0.64694(13) 0.29652(5) 0.0396(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0393(6) 0.0241(5) 0.0281(5) -0.0020(4) 0.0127(5) -0.0095(5) C9 0.0222(7) 0.0262(7) 0.0188(6) -0.0015(5) 0.0056(5) -0.0006(6) C13 0.0267(7) 0.0204(7) 0.0195(6) -0.0013(5) 0.0025(5) 0.0017(6) C11 0.0293(7) 0.0206(7) 0.0201(7) -0.0014(5) 0.0058(6) 0.0022(6) C10 0.0280(7) 0.0235(7) 0.0224(7) -0.0004(5) 0.0091(6) -0.0005(6) C5 0.0287(8) 0.0352(8) 0.0210(7) 0.0019(6) 0.0062(6) -0.0022(6) C4 0.0223(7) 0.0259(7) 0.0220(7) -0.0007(5) 0.0061(6) -0.0017(6) C3 0.0246(7) 0.0263(7) 0.0237(7) 0.0033(6) 0.0056(6) 0.0016(6) C2 0.0247(7) 0.0201(6) 0.0222(7) 0.0006(5) 0.0081(6) 0.0023(5) C8 0.0265(7) 0.0255(7) 0.0250(7) -0.0030(6) 0.0058(6) 0.0018(6) C17 0.0400(9) 0.0211(7) 0.0330(8) 0.0042(6) 0.0000(7) -0.0018(7) C14 0.0306(8) 0.0271(7) 0.0250(7) -0.0028(6) 0.0047(6) 0.0030(6) C1 0.0315(8) 0.0193(6) 0.0200(7) -0.0015(5) 0.0086(6) 0.0013(6) C18 0.0257(7) 0.0222(7) 0.0229(7) 0.0007(5) 0.0007(6) -0.0007(6) C12 0.0352(8) 0.0209(7) 0.0188(7) -0.0003(5) 0.0080(6) -0.0012(6) C7 0.0263(7) 0.0337(8) 0.0293(7) -0.0114(6) 0.0079(6) -0.0013(6) C15 0.0379(9) 0.0312(8) 0.0324(8) -0.0096(7) 0.0037(7) 0.0112(7) C6 0.0303(8) 0.0454(9) 0.0204(7) -0.0077(6) 0.0077(6) -0.0036(7) C16 0.0440(10) 0.0186(7) 0.0420(9) -0.0033(6) -0.0034(7) 0.0059(7) O4 0.0798(10) 0.0235(6) 0.0343(6) -0.0013(5) 0.0323(6) -0.0069(6) O1 0.0427(6) 0.0219(5) 0.0180(5) -0.0018(4) 0.0040(4) 0.0081(4) O2 0.0600(8) 0.0282(6) 0.0296(6) 0.0097(5) 0.0089(5) 0.0056(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 O3 C18 1.3709(18) . ? O3 C10 1.4180(16) . ? C9 O1 1.3702(16) . ? C9 C8 1.3922(19) . ? C9 C4 1.3983(19) . ? C13 C18 1.396(2) . ? C13 C14 1.404(2) . ? C13 C12 1.4644(19) . ? C11 C12 1.5106(19) . ? C11 C1 1.5438(19) . ? C11 C10 1.5452(19) . ? C11 H11 1.0000 . ? C10 C2 1.5560(19) . ? C10 H10 1.0000 . ? C5 C6 1.378(2) . ? C5 C4 1.4047(19) . ? C5 H5 0.9500 . ? C4 C3 1.4769(19) . ? C3 O2 1.2214(16) . ? C3 C2 1.5045(19) . ? C2 C1 1.5415(18) . ? C2 H2 1.0000 . ? C8 C7 1.383(2) . ? C8 H8 0.9500 . ? C17 C16 1.376(2) . ? C17 C18 1.390(2) . ? C17 H17 0.9500 . ? C14 C15 1.375(2) . ? C14 H14 0.9500 . ? C1 O1 1.4329(16) . ? C1 H1 1.0000 . ? C12 O4 1.2200(17) . ? C7 C6 1.394(2) . ? C7 H7 0.9500 . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C6 H6 0.9500 . ? C16 H16 0.9500 . ? 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 C18 O3 C10 117.44(11) . . ? O1 C9 C8 116.31(12) . . ? O1 C9 C4 122.55(12) . . ? C8 C9 C4 121.02(12) . . ? C18 C13 C14 119.02(13) . . ? C18 C13 C12 121.56(13) . . ? C14 C13 C12 119.43(13) . . ? C12 C11 C1 111.43(12) . . ? C12 C11 C10 113.94(11) . . ? C1 C11 C10 88.25(10) . . ? C12 C11 H11 113.6 . . ? C1 C11 H11 113.6 . . ? C10 C11 H11 113.6 . . ? O3 C10 C11 119.76(11) . . ? O3 C10 C2 117.49(11) . . ? C11 C10 C2 88.58(10) . . ? O3 C10 H10 109.8 . . ? C11 C10 H10 109.8 . . ? C2 C10 H10 109.8 . . ? C6 C5 C4 120.89(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C9 C4 C5 118.31(13) . . ? C9 C4 C3 120.60(12) . . ? C5 C4 C3 121.06(13) . . ? O2 C3 C4 122.73(13) . . ? O2 C3 C2 121.69(13) . . ? C4 C3 C2 115.55(11) . . ? C3 C2 C1 117.53(11) . . ? C3 C2 C10 119.31(11) . . ? C1 C2 C10 87.95(10) . . ? C3 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C10 C2 H2 110.1 . . ? C7 C8 C9 119.36(13) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C16 C17 C18 119.73(15) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C15 C14 C13 120.56(15) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? O1 C1 C2 113.13(11) . . ? O1 C1 C11 108.06(11) . . ? C2 C1 C11 89.16(10) . . ? O1 C1 H1 114.6 . . ? C2 C1 H1 114.6 . . ? C11 C1 H1 114.6 . . ? O3 C18 C17 115.82(13) . . ? O3 C18 C13 123.92(12) . . ? C17 C18 C13 120.23(14) . . ? O4 C12 C13 122.79(13) . . ? O4 C12 C11 119.92(13) . . ? C13 C12 C11 117.29(12) . . ? C8 C7 C6 120.63(14) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C14 C15 C16 119.55(15) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C5 C6 C7 119.76(13) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C17 C16 C15 120.92(14) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C9 O1 C1 117.51(10) . . ? 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 C18 O3 C10 C11 29.02(18) . . . . ? C18 O3 C10 C2 -76.38(15) . . . . ? C12 C11 C10 O3 -26.85(18) . . . . ? C1 C11 C10 O3 -139.58(13) . . . . ? C12 C11 C10 C2 94.32(13) . . . . ? C1 C11 C10 C2 -18.40(10) . . . . ? O1 C9 C4 C5 -175.47(13) . . . . ? C8 C9 C4 C5 0.4(2) . . . . ? O1 C9 C4 C3 2.5(2) . . . . ? C8 C9 C4 C3 178.43(13) . . . . ? C6 C5 C4 C9 1.2(2) . . . . ? C6 C5 C4 C3 -176.83(14) . . . . ? C9 C4 C3 O2 -169.60(14) . . . . ? C5 C4 C3 O2 8.4(2) . . . . ? C9 C4 C3 C2 8.6(2) . . . . ? C5 C4 C3 C2 -173.50(13) . . . . ? O2 C3 C2 C1 -175.32(13) . . . . ? C4 C3 C2 C1 6.51(18) . . . . ? O2 C3 C2 C10 80.42(18) . . . . ? C4 C3 C2 C10 -97.75(15) . . . . ? O3 C10 C2 C3 -97.73(14) . . . . ? C11 C10 C2 C3 139.12(12) . . . . ? O3 C10 C2 C1 141.59(12) . . . . ? C11 C10 C2 C1 18.44(10) . . . . ? O1 C9 C8 C7 174.32(13) . . . . ? C4 C9 C8 C7 -1.8(2) . . . . ? C18 C13 C14 C15 0.3(2) . . . . ? C12 C13 C14 C15 -179.16(14) . . . . ? C3 C2 C1 O1 -31.39(17) . . . . ? C10 C2 C1 O1 90.87(12) . . . . ? C3 C2 C1 C11 -140.70(12) . . . . ? C10 C2 C1 C11 -18.45(10) . . . . ? C12 C11 C1 O1 149.37(11) . . . . ? C10 C11 C1 O1 -95.53(11) . . . . ? C12 C11 C1 C2 -96.52(12) . . . . ? C10 C11 C1 C2 18.58(10) . . . . ? C10 O3 C18 C17 165.73(13) . . . . ? C10 O3 C18 C13 -16.13(19) . . . . ? C16 C17 C18 O3 178.05(13) . . . . ? C16 C17 C18 C13 -0.2(2) . . . . ? C14 C13 C18 O3 -177.89(13) . . . . ? C12 C13 C18 O3 1.5(2) . . . . ? C14 C13 C18 C17 0.2(2) . . . . ? C12 C13 C18 C17 179.58(13) . . . . ? C18 C13 C12 O4 179.38(14) . . . . ? C14 C13 C12 O4 -1.2(2) . . . . ? C18 C13 C12 C11 -0.1(2) . . . . ? C14 C13 C12 C11 179.26(13) . . . . ? C1 C11 C12 O4 -69.58(17) . . . . ? C10 C11 C12 O4 -167.54(14) . . . . ? C1 C11 C12 C13 109.96(14) . . . . ? C10 C11 C12 C13 12.00(18) . . . . ? C9 C8 C7 C6 1.7(2) . . . . ? C13 C14 C15 C16 -0.7(2) . . . . ? C4 C5 C6 C7 -1.3(2) . . . . ? C8 C7 C6 C5 -0.1(2) . . . . ? C18 C17 C16 C15 -0.3(2) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C8 C9 O1 C1 153.67(12) . . . . ? C4 C9 O1 C1 -30.3(2) . . . . ? C2 C1 O1 C9 43.23(16) . . . . ? C11 C1 O1 C9 140.26(12) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.283 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.078 # Attachment 'trans_Chromone_Dimer3.cif.txt' data_saka98_p21c _database_code_depnum_ccdc_archive 'CCDC 714211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 O4' _chemical_formula_weight 292.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5496(13) _cell_length_b 8.5832(10) _cell_length_c 14.7098(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.247(2) _cell_angle_gamma 90.00 _cell_volume 1318.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 2489 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.57 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9545 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 7195 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.42 _reflns_number_total 3043 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.5416P] 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 3043 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72817(17) 0.9626(2) 0.25252(12) 0.0373(4) Uani 1 1 d . . . H1 H 0.7315 0.9724 0.1852 0.045 Uiso 1 1 calc R . . C2 C 0.82088(17) 1.0733(2) 0.31332(12) 0.0360(4) Uani 1 1 d . . . H2 H 0.8332 1.1730 0.2806 0.043 Uiso 1 1 calc R . . C3 C 0.94627(16) 1.0093(2) 0.35884(12) 0.0361(4) Uani 1 1 d . . . C4 C 0.95553(16) 0.8381(2) 0.36116(11) 0.0332(4) Uani 1 1 d . . . C5 C 1.06723(17) 0.7653(2) 0.40439(12) 0.0376(4) Uani 1 1 d . . . H5 H 1.1383 0.8272 0.4296 0.045 Uiso 1 1 calc R . . C6 C 1.07533(18) 0.6063(2) 0.41083(13) 0.0409(4) Uani 1 1 d . . . H6 H 1.1514 0.5582 0.4403 0.049 Uiso 1 1 calc R . . C7 C 0.97062(18) 0.5155(2) 0.37358(12) 0.0411(4) Uani 1 1 d . . . H7 H 0.9762 0.4052 0.3778 0.049 Uiso 1 1 calc R . . C8 C 0.85942(18) 0.5837(2) 0.33087(12) 0.0369(4) Uani 1 1 d . . . H8 H 0.7889 0.5206 0.3059 0.044 Uiso 1 1 calc R . . C9 C 0.85097(16) 0.7451(2) 0.32448(11) 0.0321(4) Uani 1 1 d . . . C10 C 0.71128(16) 1.08775(19) 0.37243(12) 0.0326(4) Uani 1 1 d . . . H10 H 0.7148 0.9955 0.4142 0.039 Uiso 1 1 calc R . . C11 C 0.61786(16) 1.0523(2) 0.28592(11) 0.0336(4) Uani 1 1 d . . . H11 H 0.6065 1.1509 0.2495 0.040 Uiso 1 1 calc R . . C12 C 0.49085(16) 1.01174(19) 0.31168(12) 0.0332(4) Uani 1 1 d . . . C13 C 0.46402(16) 1.11725(18) 0.38793(11) 0.0306(4) Uani 1 1 d . . . C14 C 0.33933(16) 1.1291(2) 0.40778(12) 0.0342(4) Uani 1 1 d . . . H14 H 0.2742 1.0668 0.3744 0.041 Uiso 1 1 calc R . . C15 C 0.30763(18) 1.2289(2) 0.47472(12) 0.0376(4) Uani 1 1 d . . . H15 H 0.2213 1.2371 0.4858 0.045 Uiso 1 1 calc R . . C16 C 0.40278(19) 1.3168(2) 0.52569(13) 0.0417(4) Uani 1 1 d . . . H16 H 0.3821 1.3827 0.5733 0.050 Uiso 1 1 calc R . . C17 C 0.52700(18) 1.3089(2) 0.50750(13) 0.0387(4) Uani 1 1 d . . . H17 H 0.5918 1.3689 0.5430 0.046 Uiso 1 1 calc R . . C18 C 0.55847(16) 1.21374(19) 0.43745(12) 0.0321(4) Uani 1 1 d . . . O1 O 0.73454(11) 0.80383(14) 0.28610(8) 0.0368(3) Uani 1 1 d . . . O2 O 1.03252(13) 1.09512(16) 0.39248(11) 0.0527(4) Uani 1 1 d . . . O3 O 0.68420(11) 1.22038(13) 0.42176(8) 0.0354(3) Uani 1 1 d . . . O4 O 0.41550(12) 0.91463(15) 0.27671(10) 0.0471(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0446(10) 0.0351(9) 0.0320(9) 0.0006(7) 0.0043(7) 0.0011(8) C2 0.0384(9) 0.0371(9) 0.0334(9) 0.0011(7) 0.0081(7) -0.0044(7) C3 0.0320(9) 0.0388(9) 0.0392(9) -0.0090(7) 0.0107(7) -0.0030(7) C4 0.0308(8) 0.0391(9) 0.0310(8) -0.0072(7) 0.0090(6) -0.0011(7) C5 0.0304(8) 0.0468(10) 0.0366(9) -0.0077(8) 0.0078(7) -0.0002(7) C6 0.0364(9) 0.0511(11) 0.0357(9) 0.0010(8) 0.0073(7) 0.0078(8) C7 0.0510(11) 0.0372(10) 0.0364(10) 0.0003(8) 0.0106(8) 0.0040(8) C8 0.0401(9) 0.0391(10) 0.0315(9) -0.0046(7) 0.0049(7) -0.0031(7) C9 0.0324(8) 0.0392(9) 0.0256(8) -0.0052(7) 0.0070(6) 0.0007(7) C10 0.0339(9) 0.0277(8) 0.0352(9) -0.0006(7) 0.0016(7) -0.0005(6) C11 0.0375(9) 0.0289(8) 0.0323(8) 0.0040(7) -0.0026(7) 0.0018(7) C12 0.0327(8) 0.0253(8) 0.0377(9) 0.0002(7) -0.0075(7) 0.0047(6) C13 0.0328(8) 0.0233(7) 0.0335(8) 0.0038(6) -0.0028(6) 0.0010(6) C14 0.0354(9) 0.0291(8) 0.0361(9) 0.0065(7) -0.0017(7) -0.0012(7) C15 0.0407(10) 0.0333(9) 0.0392(9) 0.0078(7) 0.0074(7) 0.0015(7) C16 0.0533(11) 0.0350(9) 0.0382(10) -0.0002(8) 0.0119(8) -0.0013(8) C17 0.0462(11) 0.0314(9) 0.0369(9) -0.0042(7) 0.0004(8) -0.0054(8) C18 0.0335(8) 0.0255(8) 0.0356(9) 0.0050(7) -0.0012(7) -0.0010(6) O1 0.0327(6) 0.0364(7) 0.0393(7) -0.0034(5) -0.0014(5) -0.0005(5) O2 0.0342(7) 0.0458(8) 0.0775(11) -0.0184(7) 0.0060(7) -0.0071(6) O3 0.0323(6) 0.0303(6) 0.0418(7) -0.0039(5) -0.0005(5) -0.0030(5) O4 0.0368(7) 0.0384(7) 0.0621(9) -0.0179(6) -0.0066(6) -0.0005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.448(2) . ? C1 C11 1.534(2) . ? C1 C2 1.552(2) . ? C1 H1 1.0000 . ? C2 C3 1.498(3) . ? C2 C10 1.548(2) . ? C2 H2 1.0000 . ? C3 O2 1.219(2) . ? C3 C4 1.473(3) . ? C4 C5 1.403(2) . ? C4 C9 1.405(2) . ? C5 C6 1.369(3) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 O1 1.372(2) . ? C10 O3 1.401(2) . ? C10 C11 1.524(2) . ? C10 H10 1.0000 . ? C11 C12 1.485(2) . ? C11 H11 1.0000 . ? C12 O4 1.214(2) . ? C12 C13 1.500(2) . ? C13 C14 1.392(2) . ? C13 C18 1.415(2) . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.392(2) . ? C17 H17 0.9500 . ? C18 O3 1.380(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C11 111.31(14) . . ? O1 C1 C2 112.64(14) . . ? C11 C1 C2 87.28(13) . . ? O1 C1 H1 114.3 . . ? C11 C1 H1 114.3 . . ? C2 C1 H1 114.3 . . ? C3 C2 C10 117.45(14) . . ? C3 C2 C1 118.45(15) . . ? C10 C2 C1 85.01(12) . . ? C3 C2 H2 111.2 . . ? C10 C2 H2 111.2 . . ? C1 C2 H2 111.2 . . ? O2 C3 C4 123.37(17) . . ? O2 C3 C2 121.33(17) . . ? C4 C3 C2 115.28(15) . . ? C5 C4 C9 118.88(17) . . ? C5 C4 C3 120.24(16) . . ? C9 C4 C3 120.80(16) . . ? C6 C5 C4 121.01(17) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.37(18) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.99(18) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.70(17) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? O1 C9 C8 116.01(15) . . ? O1 C9 C4 123.83(16) . . ? C8 C9 C4 120.05(16) . . ? O3 C10 C11 116.05(14) . . ? O3 C10 C2 125.47(14) . . ? C11 C10 C2 87.74(13) . . ? O3 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C2 C10 H10 108.5 . . ? C12 C11 C10 109.44(14) . . ? C12 C11 C1 135.89(15) . . ? C10 C11 C1 86.46(12) . . ? C12 C11 H11 107.0 . . ? C10 C11 H11 107.0 . . ? C1 C11 H11 107.0 . . ? O4 C12 C11 127.77(17) . . ? O4 C12 C13 123.31(17) . . ? C11 C12 C13 108.86(14) . . ? C14 C13 C18 117.81(16) . . ? C14 C13 C12 119.11(15) . . ? C18 C13 C12 122.96(15) . . ? C15 C14 C13 121.84(16) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 119.48(17) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.25(17) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.50(17) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? O3 C18 C17 115.89(15) . . ? O3 C18 C13 124.13(15) . . ? C17 C18 C13 119.98(16) . . ? C9 O1 C1 118.75(13) . . ? C18 O3 C10 108.99(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 33.7(2) . . . . ? C11 C1 C2 C3 145.64(15) . . . . ? O1 C1 C2 C10 -84.96(15) . . . . ? C11 C1 C2 C10 27.02(12) . . . . ? C10 C2 C3 O2 -94.4(2) . . . . ? C1 C2 C3 O2 165.82(17) . . . . ? C10 C2 C3 C4 84.46(19) . . . . ? C1 C2 C3 C4 -15.3(2) . . . . ? O2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 C5 -178.19(15) . . . . ? O2 C3 C4 C9 177.38(17) . . . . ? C2 C3 C4 C9 -1.4(2) . . . . ? C9 C4 C5 C6 0.2(2) . . . . ? C3 C4 C5 C6 177.02(16) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 O1 -176.11(15) . . . . ? C7 C8 C9 C4 0.2(3) . . . . ? C5 C4 C9 O1 175.66(15) . . . . ? C3 C4 C9 O1 -1.1(2) . . . . ? C5 C4 C9 C8 -0.4(2) . . . . ? C3 C4 C9 C8 -177.15(16) . . . . ? C3 C2 C10 O3 92.5(2) . . . . ? C1 C2 C10 O3 -147.96(16) . . . . ? C3 C2 C10 C11 -146.77(16) . . . . ? C1 C2 C10 C11 -27.19(12) . . . . ? O3 C10 C11 C12 -65.86(18) . . . . ? C2 C10 C11 C12 165.30(14) . . . . ? O3 C10 C11 C1 156.32(15) . . . . ? C2 C10 C11 C1 27.48(12) . . . . ? O1 C1 C11 C12 -28.7(3) . . . . ? C2 C1 C11 C12 -142.0(2) . . . . ? O1 C1 C11 C10 85.86(15) . . . . ? C2 C1 C11 C10 -27.42(12) . . . . ? C10 C11 C12 O4 -142.66(17) . . . . ? C1 C11 C12 O4 -37.0(3) . . . . ? C10 C11 C12 C13 39.98(18) . . . . ? C1 C11 C12 C13 145.64(18) . . . . ? O4 C12 C13 C14 -13.7(2) . . . . ? C11 C12 C13 C14 163.78(14) . . . . ? O4 C12 C13 C18 170.39(16) . . . . ? C11 C12 C13 C18 -12.1(2) . . . . ? C18 C13 C14 C15 -1.3(2) . . . . ? C12 C13 C14 C15 -177.39(15) . . . . ? C13 C14 C15 C16 -1.9(3) . . . . ? C14 C15 C16 C17 2.3(3) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 O3 176.78(16) . . . . ? C16 C17 C18 C13 -3.7(3) . . . . ? C14 C13 C18 O3 -176.48(15) . . . . ? C12 C13 C18 O3 -0.5(2) . . . . ? C14 C13 C18 C17 4.1(2) . . . . ? C12 C13 C18 C17 180.00(15) . . . . ? C8 C9 O1 C1 -161.98(14) . . . . ? C4 C9 O1 C1 21.9(2) . . . . ? C11 C1 O1 C9 -132.64(15) . . . . ? C2 C1 O1 C9 -36.5(2) . . . . ? C17 C18 O3 C10 161.37(15) . . . . ? C13 C18 O3 C10 -18.1(2) . . . . ? C11 C10 O3 C18 51.10(19) . . . . ? C2 C10 O3 C18 158.23(15) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.576 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.044