# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1355 data_1 _publ_section_title ;A facile route to 3,7-cis-disubstituted 1,5-cyclooctadiene-1,2,5,6-tetracarboxylates through photochemical [2+2]cycloaddition of 3-substituted cyclobutene-1,2-dicarboxylates and thermal isomerization. Crystal and molecular structure of 1a ; _publ_section_abstract ;Photochemical dimerization of 3-substituted cyclobutene-1,2-dicarboxylates followed by thermal isomerization gives 3,7-cis-disubstituted 1,5-cyclooctadiene-1,2,5,7-tetracarboxylates. We present the crystal and molecular structure of 1a ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'HISAYUKI WATANABE' ; 722-1 Tsuboi-cho, Funabashi, Chiba 274-8507, Japan ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Cube' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _chemical_formula_moiety 'C18 H20 O6 ' _chemical_formula_weight 332.00 _cell_length_a 11.987(3) _cell_length_b 13.131(3) _cell_length_c 11.801(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 112.97(2) _cell_angle_gamma 90.000000(0) _cell_volume 1710.2(7) _cell_measurement_reflns_used '1486' _cell_measurement_theta_min '1' _cell_measurement_theta_max '70' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas 1.300 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.7686 _cell_measurement_temperature '298' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'refdelf' _diffrn_reflns_number 3677 _reflns_number_total 2542 _reflns_number_observed 1486 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.160 _diffrn_reflns_theta_max 53.71 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.098 _refine_ls_wR_factor_obs 0.119 _refine_ls_hydrogen_treatment 'refxyz' _refine_ls_number_reflns 1486 _refine_ls_number_parameters 225 _refine_ls_goodness_of_fit_obs 1.732 _refine_ls_weighting_scheme 'Cruickshank' _refine_ls_shift/esd_max 0.8550 _refine_ls_shift/esd_mean 0.0572 _refine_diff_density_min -0.44 _refine_diff_density_max 0.70 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 -0.05201 _diffrn_orient_matrix_UB_12 -0.05130 _diffrn_orient_matrix_UB_13 -0.06013 _diffrn_orient_matrix_UB_21 0.05818 _diffrn_orient_matrix_UB_22 -0.00128 _diffrn_orient_matrix_UB_23 -0.04188 _diffrn_orient_matrix_UB_31 0.04603 _diffrn_orient_matrix_UB_32 -0.05625 _diffrn_orient_matrix_UB_33 0.05566 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z -X+0.5,+Y+0.5,-Z +X+0.5,-Y+0.5,+Z _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_cell_setting 'Monoclinic' #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.4573(7) -0.1203(4) 0.3299(6) 0.077(5) 1.000 Uij O2 0.5794(7) 0.0091(5) 0.4272(6) 0.073(5) 1.000 Uij O3 0.4713(6) 0.1351(6) -0.0871(6) 0.085(5) 1.000 Uij O4 0.5144(7) 0.2734(6) 0.0366(7) 0.093(5) 1.000 Uij C5 0.3890(8) 0.0420(6) 0.2557(7) 0.050(5) 1.000 Uij O6 0.3887(7) -0.0133(6) -0.1729(7) 0.092(5) 1.000 Uij C7 0.3274(8) 0.2054(6) 0.1308(8) 0.057(5) 1.000 Uij C8 0.3065(8) -0.0214(6) 0.1841(8) 0.052(5) 1.000 Uij C9 0.3640(9) 0.2060(7) 0.3582(8) 0.056(6) 1.000 Uij C10 0.4003(8) 0.1570(6) 0.2562(8) 0.050(5) 1.000 Uij C11 0.3129(7) 0.0742(6) -0.0373(8) 0.050(5) 1.000 Uij O12 0.2999(9) -0.2049(5) 0.1943(7) 0.103(5) 1.000 Uij C13 0.3567(7) 0.1570(6) 0.0309(8) 0.051(5) 1.000 Uij C14 0.1941(8) -0.0067(6) 0.0750(8) 0.060(5) 1.000 Uij C15 0.3889(8) 0.0557(9) -0.1102(9) 0.064(6) 1.000 Uij C16 0.3484(12) -0.1251(7) 0.2317(10) 0.071(7) 1.000 Uij C17 0.2126(8) 0.0025(6) -0.0474(8) 0.058(5) 1.000 Uij C18 0.4865(9) -0.0160(7) 0.3482(8) 0.057(6) 1.000 Uij C19 0.4544(9) 0.1999(9) -0.0016(9) 0.065(6) 1.000 Uij C20 0.2416(10) 0.1815(8) 0.3524(9) 0.080(7) 1.000 Uij C21 0.0943(9) 0.0314(9) -0.1511(10) 0.076(7) 1.000 Uij C22 0.0911(12) 0.0415(9) -0.2769(10) 0.087(8) 1.000 Uij C23 0.2168(11) 0.2220(10) 0.4604(11) 0.098(8) 1.000 Uij C24 -0.0308(14) 0.0766(11) -0.3687(13) 0.12(1) 1.000 Uij H7A 0.34540 0.27680 0.13340 0.050 1.000 Uiso H7B 0.24280 0.19630 0.11320 0.050 1.000 Uiso H9A 0.41590 0.24760 0.42480 0.050 1.000 Uiso H10 0.48320 0.17460 0.27450 0.050 1.000 Uiso H14A 0.15640 0.05460 0.08700 0.050 1.000 Uiso H14B 0.14270 -0.06380 0.07060 0.050 1.000 Uiso H17 0.23260 -0.06420 -0.06690 0.050 1.000 Uiso H20A 0.18390 0.21170 0.27870 0.050 1.000 Uiso H20B 0.23060 0.10900 0.34910 0.050 1.000 Uiso H21A 0.02220 0.04690 -0.13740 0.050 1.000 Uiso H22A 0.15180 0.08920 -0.27680 0.050 1.000 Uiso H22B 0.10810 -0.02410 -0.30220 0.050 1.000 Uiso H23A 0.13600 0.20580 0.45230 0.050 1.000 Uiso H23B 0.22730 0.29460 0.46410 0.050 1.000 Uiso H23C 0.27390 0.19190 0.53450 0.050 1.000 Uiso H24A -0.03080 0.08130 -0.44990 0.050 1.000 Uiso H24B -0.04790 0.14230 -0.34360 0.050 1.000 Uiso H24C -0.09160 0.02890 -0.36900 0.050 1.000 Uiso H9B 0.432(6) 0.181(5) 0.432(6) 0.02(2) 1.000 Uiso H21B 0.065(7) 0.110(7) -0.153(7) 0.06(3) 1.000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.118(6) 0.033(4) 0.069(5) 0.016(4) 0.049(5) 0.009(3) O2 0.073(5) 0.080(5) 0.057(4) 0.015(4) 0.030(4) 0.013(4) O3 0.064(4) 0.112(6) 0.076(5) -0.001(4) 0.050(4) 0.017(4) O4 0.078(5) 0.091(6) 0.099(6) -0.027(5) 0.045(5) 0.019(5) C5 0.057(5) 0.044(5) 0.047(5) 0.003(5) 0.037(4) 0.003(4) O6 0.098(6) 0.097(6) 0.077(5) 0.024(5) 0.060(4) -0.002(4) C7 0.066(6) 0.031(5) 0.065(6) -0.001(4) 0.034(5) 0.003(4) C8 0.065(6) 0.038(5) 0.049(5) -0.005(4) 0.039(5) 0.001(4) C9 0.060(6) 0.054(5) 0.046(5) 0.005(5) 0.021(5) -0.010(4) C10 0.047(5) 0.041(4) 0.055(5) 0.004(4) 0.026(4) -0.001(4) C11 0.048(5) 0.048(5) 0.052(5) 0.007(4) 0.035(4) 0.009(4) O12 0.166(8) 0.035(4) 0.089(5) -0.007(5) 0.056(5) 0.004(4) C13 0.052(5) 0.038(5) 0.058(5) 0.003(4) 0.031(4) 0.013(4) C14 0.067(6) 0.040(5) 0.068(6) -0.005(4) 0.045(5) 0.002(4) C15 0.049(6) 0.077(7) 0.059(6) 0.009(5) 0.030(5) 0.013(5) C16 0.111(9) 0.030(5) 0.065(7) 0.009(5) 0.053(7) 0.007(5) C17 0.071(6) 0.038(5) 0.061(5) -0.006(5) 0.041(5) -0.002(4) C18 0.059(6) 0.065(6) 0.041(5) 0.019(5) 0.025(5) 0.007(5) C19 0.050(5) 0.072(7) 0.064(6) -0.011(5) 0.024(5) 0.016(5) C20 0.077(7) 0.080(8) 0.073(7) 0.011(6) 0.041(6) -0.012(6) C21 0.061(6) 0.090(8) 0.069(7) -0.002(6) 0.032(5) 0.009(6) C22 0.107(9) 0.072(7) 0.068(7) 0.003(7) 0.036(7) -0.002(6) C23 0.094(8) 0.104(9) 0.089(8) 0.018(7) 0.054(7) -0.018(7) C24 0.13(1) 0.10(1) 0.10(1) -0.01(1) 0.03(1) 0.00(1) 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 C16 O1 C18 O2 -178.2(12) . . . . yes C16 O1 C18 C5 0.1(8) . . . . yes C18 O1 C16 C8 0.7(8) . . . . yes C18 O1 C16 O12 -179.8(14) . . . . yes C15 O3 C19 O4 178.6(14) . . . . yes C19 O3 C15 O6 -175.0(14) . . . . yes C19 O3 C15 C11 2.0(8) . . . . yes C15 O3 C19 C13 0.7(8) . . . . yes C8 C5 C10 C7 -22.6(10) . . . . yes C8 C5 C10 C9 102.1(12) . . . . yes C10 C5 C8 C14 1.5(9) . . . . yes C10 C5 C8 C16 179.7(14) . . . . yes C8 C5 C18 O1 -1.0(8) . . . . yes C8 C5 C18 O2 177.1(15) . . . . yes C18 C5 C8 C14 -176.9(14) . . . . yes C18 C5 C8 C16 1.3(8) . . . . yes C10 C5 C18 O1 -179.6(11) . . . . yes C10 C5 C18 O2 -1.6(10) . . . . yes C18 C5 C10 C7 155.7(11) . . . . yes C18 C5 C10 C9 -79.6(9) . . . . yes C13 C7 C10 C5 -52.5(8) . . . . yes C13 C7 C10 C9 -177.7(10) . . . . yes C10 C7 C13 C11 85.5(11) . . . . yes C10 C7 C13 C19 -91.2(10) . . . . yes C5 C8 C14 C17 83.4(12) . . . . yes C5 C8 C16 O1 -1.3(9) . . . . yes C5 C8 C16 O12 179.3(15) . . . . yes C14 C8 C16 O1 177.2(13) . . . . yes C14 C8 C16 O12 -2.2(11) . . . . yes C16 C8 C14 C17 -94.6(11) . . . . yes C20 C9 C10 C5 -56.4(9) . . . . yes C20 C9 C10 C7 69.9(9) . . . . yes C10 C9 C20 C23 174.0(13) . . . . yes C13 C11 C15 O3 -4.2(8) . . . . yes C13 C11 C15 O6 172.5(15) . . . . yes C15 C11 C13 C7 -172.4(13) . . . . yes C15 C11 C13 C19 4.5(8) . . . . yes C17 C11 C13 C7 5.2(9) . . . . yes C13 C11 C17 C14 -30.1(10) . . . . yes C17 C11 C13 C19 -177.8(14) . . . . yes C13 C11 C17 C21 94.4(12) . . . . yes C17 C11 C15 O3 177.8(12) . . . . yes C17 C11 C15 O6 -5.6(11) . . . . yes C15 C11 C17 C14 147.3(11) . . . . yes C15 C11 C17 C21 -88.2(10) . . . . yes C7 C13 C19 O3 173.9(12) . . . . yes C7 C13 C19 O4 -3.8(11) . . . . yes C11 C13 C19 O3 -3.5(8) . . . . yes C11 C13 C19 O4 178.8(15) . . . . yes C8 C14 C17 C11 -46.9(8) . . . . yes C8 C14 C17 C21 -172.5(11) . . . . yes C11 C17 C21 C22 55.9(10) . . . . yes C14 C17 C21 C22 -178.4(13) . . . . yes C17 C21 C22 C24 -176.6(15) . . . . yes C8 C5 C10 H10 -139.6(14) . . . . yes C18 C5 C10 H10 38.7(9) . . . . yes C13 C7 C10 H10 66.4(8) . . . . yes H7A C7 C10 C5 -173.0(11) . . . . yes H7A C7 C10 C9 61.9(9) . . . . yes H7A C7 C10 H10 -54.0(9) . . . . yes H7B C7 C10 C5 67.6(9) . . . . yes H7B C7 C10 C9 -57.6(8) . . . . yes H7B C7 C10 H10 -173.5(11) . . . . yes H7A C7 C13 C11 -153.5(14) . . . . yes H7A C7 C13 C19 29.8(9) . . . . yes H7B C7 C13 C11 -34.0(10) . . . . yes H7B C7 C13 C19 149.3(12) . . . . yes C5 C8 C14 H14A -37.4(10) . . . . yes C5 C8 C14 H14B -155.1(15) . . . . yes C16 C8 C14 H14A 144.6(12) . . . . yes C16 C8 C14 H14B 26.8(9) . . . . yes C20 C9 C10 H10 -175.6(12) . . . . yes C10 C9 C20 H20A -66.4(10) . . . . yes C10 C9 C20 H20B 52.7(10) . . . . yes H9A C9 C10 C5 120.8(13) . . . . yes H9A C9 C10 C7 -112.9(12) . . . . yes H9A C9 C10 H10 1.7(10) . . . . yes H9B C9 C10 C5 67.9(40) . . . . yes H9B C9 C10 C7 -165.8(41) . . . . yes H9B C9 C10 H10 -51.2(40) . . . . yes H9A C9 C20 C23 -3.4(10) . . . . yes H9A C9 C20 H20A 116.2(13) . . . . yes H9A C9 C20 H20B -124.8(14) . . . . yes H9B C9 C20 C23 58.3(44) . . . . yes H9B C9 C20 H20A 177.8(45) . . . . yes H9B C9 C20 H20B -63.1(44) . . . . yes C13 C11 C17 H17 -148.4(14) . . . . yes C15 C11 C17 H17 29.0(9) . . . . yes C8 C14 C17 H17 72.7(9) . . . . yes H14A C14 C17 C11 73.4(9) . . . . yes H14A C14 C17 C21 -52.2(9) . . . . yes H14A C14 C17 H17 -167.0(11) . . . . yes H14B C14 C17 C11 -167.0(11) . . . . yes H14B C14 C17 C21 67.3(9) . . . . yes H14B C14 C17 H17 -47.5(9) . . . . yes C11 C17 C21 H21A -120.7(14) . . . . yes C11 C17 C21 H21B -50.8(51) . . . . yes C14 C17 C21 H21A 4.9(10) . . . . yes C14 C17 C21 H21B 74.8(52) . . . . yes H17 C17 C21 C22 -62.9(11) . . . . yes H17 C17 C21 H21A 120.4(14) . . . . yes H17 C17 C21 H21B -169.7(52) . . . . yes C9 C20 C23 H23A 178.7(15) . . . . yes C9 C20 C23 H23B 58.1(11) . . . . yes C9 C20 C23 H23C -60.9(11) . . . . yes H20A C20 C23 H23A 59.3(12) . . . . yes H20A C20 C23 H23B -61.3(12) . . . . yes H20A C20 C23 H23C 179.7(14) . . . . yes H20B C20 C23 H23A -59.1(12) . . . . yes H20B C20 C23 H23B -179.8(15) . . . . yes H20B C20 C23 H23C 61.2(12) . . . . yes C17 C21 C22 H22A -55.3(11) . . . . yes C17 C21 C22 H22B 63.8(12) . . . . yes H21A C21 C22 C24 0.2(11) . . . . yes H21A C21 C22 H22A 121.5(16) . . . . yes H21A C21 C22 H22B -119.4(15) . . . . yes H21B C21 C22 C24 -55.5(46) . . . . yes H21B C21 C22 H22A 65.8(47) . . . . yes H21B C21 C22 H22B -175.1(47) . . . . yes C21 C22 C24 H24A -178.9(17) . . . . yes C21 C22 C24 H24B 60.8(13) . . . . yes C21 C22 C24 H24C -58.3(13) . . . . yes H22A C22 C24 H24A 59.3(14) . . . . yes H22A C22 C24 H24B -61.0(14) . . . . yes H22A C22 C24 H24C 179.9(17) . . . . yes H22B C22 C24 H24A -59.6(14) . . . . yes H22B C22 C24 H24B -179.9(17) . . . . yes H22B C22 C24 H24C 61.0(14) . . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C16 1.368(15) . . yes O1 C18 1.409(12) . . yes O2 C18 1.186(12) . . yes O3 C15 1.388(13) . . yes O3 C19 1.394(13) . . yes O4 C19 1.183(14) . . yes C5 C8 1.316(12) . . yes C5 C10 1.516(12) . . yes C5 C18 1.463(13) . . yes O6 C15 1.169(14) . . yes C7 C10 1.532(12) . . yes C7 C13 1.497(12) . . yes C8 C14 1.468(13) . . yes C8 C16 1.484(13) . . yes C9 C10 1.569(13) . . yes C9 C20 1.477(15) . . yes C11 C13 1.333(12) . . yes C11 C15 1.497(13) . . yes C11 C17 1.495(12) . . yes O12 C16 1.196(13) . . yes C13 C19 1.479(13) . . yes C14 C17 1.549(13) . . yes C17 C21 1.516(14) . . yes C20 C23 1.514(16) . . yes C21 C22 1.476(16) . . yes C22 C24 1.51(2) . . yes C7 H7A 0.960(9) . . yes C7 H7B 0.960(9) . . yes C9 H9A 0.960(10) . . yes C9 H9B 0.99(7) . . yes C10 H10 0.959(9) . . yes C14 H14A 0.960(9) . . yes C14 H14B 0.959(9) . . yes C17 H17 0.959(9) . . yes C20 H20A 0.961(11) . . yes C20 H20B 0.960(11) . . yes C21 H21A 0.961(11) . . yes C21 H21B 1.09(10) . . yes C22 H22A 0.960(13) . . yes C22 H22B 0.959(12) . . yes C23 H23A 0.959(12) . . yes C23 H23B 0.960(13) . . yes C23 H23C 0.960(12) . . yes C24 H24A 0.960(14) . . yes C24 H24B 0.960(15) . . yes C24 H24C 0.960(16) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O1 C18 105.8(7) . . . yes C15 O3 C19 107.9(8) . . . yes C8 C5 C10 132.5(8) . . . yes C8 C5 C18 109.3(8) . . . yes C10 C5 C18 118.1(8) . . . yes C10 C7 C13 111.3(7) . . . yes C5 C8 C14 133.0(8) . . . yes C5 C8 C16 106.2(8) . . . yes C14 C8 C16 120.8(8) . . . yes C10 C9 C20 116.3(8) . . . yes C5 C10 C7 113.1(7) . . . yes C5 C10 C9 111.1(7) . . . yes C7 C10 C9 110.3(7) . . . yes C13 C11 C15 107.1(8) . . . yes C13 C11 C17 132.6(8) . . . yes C15 C11 C17 120.2(8) . . . yes C7 C13 C11 131.6(8) . . . yes C7 C13 C19 119.7(8) . . . yes C11 C13 C19 108.6(8) . . . yes C8 C14 C17 114.3(8) . . . yes O3 C15 O6 122.1(9) . . . yes O3 C15 C11 108.1(9) . . . yes O6 C15 C11 129.6(10) . . . yes O1 C16 C8 110.4(8) . . . yes O1 C16 O12 121.3(9) . . . yes C8 C16 O12 128.3(11) . . . yes C11 C17 C14 112.2(7) . . . yes C11 C17 C21 112.1(8) . . . yes C14 C17 C21 110.1(8) . . . yes O1 C18 O2 119.4(9) . . . yes O1 C18 C5 108.2(8) . . . yes O2 C18 C5 132.3(9) . . . yes O3 C19 O4 122.4(9) . . . yes O3 C19 C13 108.0(9) . . . yes O4 C19 C13 129.6(10) . . . yes C9 C20 C23 113.7(9) . . . yes C17 C21 C22 118.9(10) . . . yes C21 C22 C24 112.7(11) . . . yes C10 C7 H7A 109.7(8) . . . yes C10 C7 H7B 108.3(8) . . . yes C13 C7 H7A 108.7(8) . . . yes C13 C7 H7B 109.2(8) . . . yes H7A C7 H7B 109.5(9) . . . yes C10 C9 H9A 125.2(9) . . . yes C10 C9 H9B 99.4(40) . . . yes C20 C9 H9A 118.5(9) . . . yes C20 C9 H9B 115.3(40) . . . yes H9A C9 H9B 54.5(39) . . . yes C5 C10 H10 108.9(8) . . . yes C7 C10 H10 105.5(8) . . . yes C9 C10 H10 107.6(8) . . . yes C8 C14 H14A 107.7(8) . . . yes C8 C14 H14B 107.2(8) . . . yes C17 C14 H14A 108.6(8) . . . yes C17 C14 H14B 109.5(8) . . . yes H14A C14 H14B 109.5(9) . . . yes C11 C17 H17 109.0(9) . . . yes C14 C17 H17 107.0(8) . . . yes C21 C17 H17 106.1(9) . . . yes C9 C20 H20A 107.7(10) . . . yes C9 C20 H20B 109.6(10) . . . yes C23 C20 H20A 108.0(10) . . . yes C23 C20 H20B 108.3(10) . . . yes H20A C20 H20B 109.5(11) . . . yes C17 C21 H21A 122.4(10) . . . yes C17 C21 H21B 116.6(44) . . . yes C22 C21 H21A 118.6(11) . . . yes C22 C21 H21B 90.6(43) . . . yes H21A C21 H21B 60.0(45) . . . yes C21 C22 H22A 109.6(11) . . . yes C21 C22 H22B 107.9(11) . . . yes C24 C22 H22A 108.8(11) . . . yes C24 C22 H22B 108.3(11) . . . yes H22A C22 H22B 109.5(13) . . . yes C20 C23 H23A 111.1(11) . . . yes C20 C23 H23B 108.8(11) . . . yes C20 C23 H23C 108.5(11) . . . yes H23A C23 H23B 109.5(12) . . . yes H23A C23 H23C 109.4(12) . . . yes H23B C23 H23C 109.4(12) . . . yes C22 C24 H24A 111.0(14) . . . yes C22 C24 H24B 108.4(13) . . . yes C22 C24 H24C 108.9(13) . . . yes H24A C24 H24B 109.5(14) . . . yes H24A C24 H24C 109.5(14) . . . yes H24B C24 H24C 109.5(16) . . . yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C18 3.05(1) 1_555 2_656 ? O3 C15 3.39(1) 1_555 2_655 ? O3 C16 3.24(1) 1_555 2_655 ? O4 H7B 2.557(7) 1_555 4_665 ? C5 O6 3.20(1) 1_555 2_655 ? C5 C15 3.91(1) 1_555 2_655 ? O6 C18 3.01(1) 1_555 2_655 ? O6 C19 3.28(1) 1_555 2_655 ? C7 H17 3.133(8) 1_555 3_555 ? C10 C23 3.95(1) 1_555 4_665 ? C11 C15 3.72(1) 1_555 2_655 ? O12 C13 3.16(1) 1_555 3_545 ? O12 C19 3.26(1) 1_555 3_545 ? C13 C15 3.97(1) 1_555 2_655 ? C14 C21 3.91(1) 1_555 2_555 ? C14 H21A 3.006(9) 1_555 2_555 ? C15 C15 3.25(1) 1_555 2_655 ? C15 C18 3.70(1) 1_555 2_655 ? C15 C19 3.82(2) 1_555 2_655 ? C17 H7A 3.122(8) 1_555 3_545 ? C18 C18 3.49(1) 1_555 2_656 ? C23 C24 3.93(2) 1_555 4_666 ? C23 H10 3.11(1) 1_555 4_565 ? C24 C24 4.00(2) 1_555 2_554 ? H7A H17 2.2970 1_555 3_555 ? O2 C18 3.05(1) 1_555 2_656 ? O3 C15 3.39(1) 1_555 2_655 ? O3 C16 3.24(1) 1_555 2_655 ? O4 H7B 2.557(7) 1_555 4_665 ? C5 O6 3.20(1) 1_555 2_655 ? C5 C15 3.91(1) 1_555 2_655 ? O6 C18 3.01(1) 1_555 2_655 ? O6 C19 3.28(1) 1_555 2_655 ? C7 H17 3.133(8) 1_555 3_555 ? C10 C23 3.95(1) 1_555 4_665 ? C11 C15 3.72(1) 1_555 2_655 ? O12 C13 3.16(1) 1_555 3_545 ? O12 C19 3.26(1) 1_555 3_545 ? C13 C15 3.97(1) 1_555 2_655 ? C14 C21 3.91(1) 1_555 2_555 ? C14 H21A 3.006(9) 1_555 2_555 ? C15 C15 3.25(1) 1_555 2_655 ? C15 C18 3.70(1) 1_555 2_655 ? C15 C19 3.82(2) 1_555 2_655 ? C17 H7A 3.122(8) 1_555 3_545 ? C18 C18 3.49(1) 1_555 2_656 ? C23 C24 3.93(2) 1_555 4_666 ? C23 H10 3.11(1) 1_555 4_565 ? C24 C24 4.00(2) 1_555 2_554 ? H7A H17 2.2970 1_555 3_555 ? #===================================================END data_2 _publ_section_title ;A facile route to 3,7-cis-disubstituted 1,5-cyclooctadiene-1,2,5,6-tetracarboxylates through photochemical [2+2]cycloaddition of 3-substituted cyclobutene-1,2-dicarboxylates and thermal isomerization. Crystal and molecular structure of 3i ; _publ_section_abstract ;Photochemical dimerization of 3-substituted cyclobutene-1,2-dicarboxylates followed by thermal isomerization gives 3,7-cis-disubstituted 1,5-cyclooctadiene-1,2,5,7-tetracarboxylates. We present the crystal and molecular structure of 3i ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'HISAYUKI WATANABE' ; 722-1 Tsuboi-cho, Funabashi, Chiba 274-8507, Japan ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Cube' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _chemical_formula_moiety 'C22 H28 O12 ' _chemical_formula_weight 484.00 _cell_length_a 16.866(3) _cell_length_b 10.100(2) _cell_length_c 14.408(3) _cell_angle_alpha 90.000000(0) _cell_angle_beta 93.43(2) _cell_angle_gamma 90.000000(0) _cell_volume 2450.0(8) _cell_measurement_reflns_used '2746' _cell_measurement_theta_min '1' _cell_measurement_theta_max '70' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_meas 1.300 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 1.009 _cell_measurement_temperature '298' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'refdelf' _diffrn_reflns_number 2746 _reflns_number_total 1980 _reflns_number_observed 1873 _reflns_observed_criterion 'refl_observed_if_I_>_3.00_sigma(I)' _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_theta_max 24.80 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.114 _refine_ls_wR_factor_obs 0.117 _refine_ls_hydrogen_treatment 'refxyz' _refine_ls_number_reflns 1873 _refine_ls_number_parameters 175 _refine_ls_goodness_of_fit_obs 3.530 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.0487 _refine_ls_shift/esd_mean 0.0107 _refine_diff_density_min -0.41 _refine_diff_density_max 1.15 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.03658 _diffrn_orient_matrix_UB_12 0.05970 _diffrn_orient_matrix_UB_13 0.03776 _diffrn_orient_matrix_UB_21 -0.02744 _diffrn_orient_matrix_UB_22 0.07898 _diffrn_orient_matrix_UB_23 -0.02883 _diffrn_orient_matrix_UB_31 -0.03791 _diffrn_orient_matrix_UB_32 0.00046 _diffrn_orient_matrix_UB_33 0.05077 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z -X+0.5,-Y+0.5,-Z +X+0.5,+Y+0.5,+Z -X,+Y,-Z+0.5 +X,-Y,+Z+0.5 +X+0.5,-Y+0.5,+Z+0.5 -X+0.5,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_cell_setting 'Monoclinic' #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.2949(3) -0.0248(5) 0.8526(3) 0.046(2) 1.000 Uij O2 0.3553(3) -0.1387(5) 0.6904(3) 0.058(3) 1.000 Uij O3 0.4281(3) 0.3425(5) 0.8795(3) 0.056(3) 1.000 Uij O4 0.4002(3) -0.1141(5) 0.9298(3) 0.061(3) 1.000 Uij C5 0.4049(3) 0.0736(6) 0.7275(4) 0.035(3) 1.000 Uij C6 0.5579(4) 0.1767(6) 0.8326(4) 0.040(3) 1.000 Uij C7 0.4194(3) 0.0574(6) 0.8190(4) 0.034(3) 1.000 Uij C8 0.3734(4) -0.0374(6) 0.8726(4) 0.039(3) 1.000 Uij C9 0.4843(4) 0.1258(6) 0.8790(4) 0.037(3) 1.000 Uij O10 0.2911(4) 0.0333(7) 0.6255(4) 0.088(4) 1.000 Uij C11 0.4503(5) 0.2329(8) 0.9392(5) 0.051(4) 1.000 Uij O12 0.4072(4) 0.4644(8) 1.0046(5) 0.105(5) 1.000 Uij C13 0.3437(4) -0.0128(7) 0.6765(4) 0.047(4) 1.000 Uij C14 0.2432(5) -0.1171(9) 0.8982(6) 0.063(5) 1.000 Uij C15 0.2971(7) -0.2297(11) 0.6489(8) 0.087(6) 1.000 Uij C16 0.4131(5) 0.4552(9) 0.9191(8) 0.077(6) 1.000 Uij C17 0.4037(9) 0.5646(10) 0.8497(10) 0.103(8) 1.000 Uij H11A 0.401(4) 0.200(6) 0.969(4) 0.04(2) 1.000 Uiso H9 0.502(3) 0.070(6) 0.908(4) 0.02(2) 1.000 Uiso H11B 0.486(5) 0.260(8) 0.984(5) 0.06(2) 1.000 Uiso H14A 0.187(7) -0.108(12) 0.884(8) 0.12(4) 1.000 Uiso H14B 0.252(9) -0.106(15) 0.964(11) 0.17(5) 1.000 Uiso H14C 0.25808 -0.20536 0.88157 0.3(1) 1.000 Uiso H17A 0.39244 0.64766 0.87836 0.23(8) 1.000 Uiso H17B 0.36114 0.54286 0.80506 0.19(7) 1.000 Uiso H17C 0.45214 0.57216 0.81816 0.22(8) 1.000 Uiso H15A 0.30573 -0.32261 0.65935 0.18(6) 1.000 Uiso H15B 0.29463 -0.21511 0.58285 0.11(4) 1.000 Uiso H15C 0.24673 -0.20731 0.67235 0.20(7) 1.000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.039(2) 0.048(3) 0.052(3) -0.002(2) 0.015(2) 0.009(2) O2 0.061(3) 0.048(3) 0.064(3) -0.010(2) -0.003(3) -0.015(3) O3 0.065(3) 0.046(3) 0.057(3) 0.014(2) 0.004(2) -0.018(2) O4 0.066(3) 0.061(3) 0.056(3) -0.007(3) 0.002(3) 0.025(3) C5 0.033(3) 0.034(3) 0.039(3) 0.002(2) 0.006(3) 0.004(3) C6 0.041(3) 0.036(3) 0.042(4) -0.002(3) 0.011(3) -0.010(3) C7 0.035(3) 0.032(3) 0.035(3) 0.002(2) 0.007(2) 0.001(2) C8 0.043(4) 0.038(3) 0.036(3) 0.001(3) 0.011(3) 0.004(3) C9 0.042(4) 0.034(3) 0.034(3) 0.004(3) 0.004(3) -0.001(3) O10 0.079(4) 0.095(5) 0.087(4) -0.031(4) -0.038(4) 0.035(4) C11 0.056(5) 0.054(4) 0.044(4) 0.003(4) 0.011(4) -0.010(3) O12 0.106(5) 0.105(6) 0.105(6) 0.016(5) 0.030(4) -0.044(5) C13 0.050(4) 0.056(4) 0.034(3) -0.009(3) 0.005(3) 0.008(3) C14 0.058(5) 0.070(5) 0.060(5) -0.018(4) 0.020(4) 0.010(4) C15 0.098(8) 0.074(7) 0.088(8) -0.035(6) -0.002(6) -0.023(5) C16 0.056(5) 0.067(6) 0.107(8) 0.007(4) 0.003(5) -0.028(6) C17 0.11(1) 0.05(1) 0.14(1) 0.02(1) -0.02(1) -0.01(1) 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 O1 C8 O4 -5.0(7) . . . . yes C14 O1 C8 C7 177.5(8) . . . . yes C15 O2 C13 C5 176.5(10) . . . . yes C15 O2 C13 O10 -5.8(8) . . . . yes C16 O3 C11 C9 -166.1(9) . . . . yes C11 O3 C16 O12 -9.7(9) . . . . yes C11 O3 C16 C17 170.9(12) . . . . yes C6 C5 C7 C8 173.4(10) . . . . yes C6 C5 C7 C9 -9.3(6) . . . . yes C6 C5 C13 O2 129.7(8) . . . . yes C6 C5 C13 O10 -48.1(7) . . . . yes C7 C5 C13 O2 -52.8(7) . . . . yes C13 C5 C7 C8 -3.8(6) . . . . yes C13 C5 C7 C9 173.5(10) . . . . yes C7 C5 C13 O10 129.4(10) . . . . yes C5 C6 C9 C7 -50.2(6) . . . . yes C5 C6 C9 C11 179.3(8) . . . . yes C5 C7 C8 O1 -47.5(6) . . . . yes C5 C7 C8 O4 135.1(10) . . . . yes C5 C7 C9 C6 -24.1(6) . . . . yes C5 C7 C9 C11 106.1(8) . . . . yes C9 C7 C8 O1 134.8(7) . . . . yes C9 C7 C8 O4 -42.6(7) . . . . yes C8 C7 C9 C6 153.4(8) . . . . yes C8 C7 C9 C11 -76.4(7) . . . . yes C6 C9 C11 O3 60.8(6) . . . . yes C7 C9 C11 O3 -73.5(7) . . . . yes C8 O1 C14 H14A -179.8(77) . . . . yes C8 O1 C14 H14B 58.9(99) . . . . yes C8 O1 C14 H14C -58.6(8) . . . . yes C13 O2 C15 H15A -179.9(14) . . . . yes C13 O2 C15 H15B 58.5(9) . . . . yes C13 O2 C15 H15C -58.5(9) . . . . yes C16 O3 C11 H11A 73.8(37) . . . . yes C16 O3 C11 H11B -45.2(53) . . . . yes C5 C6 C9 H9 61.1(44) . . . . yes C5 C7 C9 H9 -134.2(45) . . . . yes C8 C7 C9 H9 43.3(44) . . . . yes C6 C9 C11 H11A 178.9(38) . . . . yes C6 C9 C11 H11B -59.1(54) . . . . yes C7 C9 C11 H11A 44.7(37) . . . . yes C7 C9 C11 H11B 166.6(54) . . . . yes H9 C9 C11 O3 172.2(47) . . . . yes H9 C9 C11 H11A -69.7(59) . . . . yes H9 C9 C11 H11B 52.3(71) . . . . yes O3 C16 C17 H17A 179.7(15) . . . . yes O3 C16 C17 H17B 58.9(11) . . . . yes O3 C16 C17 H17C -59.6(11) . . . . yes O12 C16 C17 H17A 0.4(11) . . . . yes O12 C16 C17 H17B -120.5(16) . . . . yes O12 C16 C17 H17C 121.0(16) . . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.343(8) . . yes O1 C14 1.460(10) . . yes O2 C13 1.300(9) . . yes O2 C15 1.447(13) . . yes O3 C11 1.438(10) . . yes O3 C16 1.305(11) . . yes O4 C8 1.200(8) . . yes C5 C6 1.513(9) . 5_656 yes C5 C7 1.337(9) . . yes C5 C13 1.508(10) . . yes C6 C9 1.535(9) . . yes C7 C8 1.479(9) . . yes C7 C9 1.519(9) . . yes C9 C11 1.519(11) . . yes O10 C13 1.210(10) . . yes O12 C16 1.246(14) . . yes C16 C17 1.492(16) . . yes C9 H9 0.75(6) . . yes C11 H11A 1.02(7) . . yes C11 H11B 0.90(8) . . yes C14 H14A 0.96(12) . . yes C14 H14B 0.96(16) . . yes C14 H14C 0.961(9) . . yes C15 H15A 0.960(11) . . yes C15 H15B 0.961(11) . . yes C15 H15C 0.961(12) . . yes C17 H17A 0.960(12) . . yes C17 H17B 0.960(15) . . yes C17 H17C 0.961(15) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 C14 116.8(6) . . . yes C13 O2 C15 117.8(7) . . . yes C11 O3 C16 117.4(7) . . . yes C6 C5 C7 126.2(6) 5_656 . . yes C6 C5 C13 114.5(6) 5_656 . . yes C7 C5 C13 119.3(6) . . . yes C5 C6 C9 113.1(5) 5_656 . . yes C5 C7 C8 121.6(6) . . . yes C5 C7 C9 126.0(6) . . . yes C8 C7 C9 112.4(5) . . . yes O1 C8 O4 122.4(6) . . . yes O1 C8 C7 111.6(6) . . . yes O4 C8 C7 126.0(6) . . . yes C6 C9 C7 118.6(6) . . . yes C6 C9 C11 110.7(6) . . . yes C7 C9 C11 111.4(6) . . . yes O3 C11 C9 107.5(6) . . . yes O2 C13 C5 113.5(6) . . . yes O2 C13 O10 124.6(7) . . . yes C5 C13 O10 121.9(7) . . . yes O3 C16 O12 121.8(9) . . . yes O3 C16 C17 111.6(10) . . . yes O12 C16 C17 126.6(10) . . . yes C6 C9 H9 100.8(43) . . . yes C7 C9 H9 102.9(43) . . . yes C11 C9 H9 111.6(43) . . . yes O3 C11 H11A 108.1(35) . . . yes O3 C11 H11B 109.6(51) . . . yes C9 C11 H11A 111.2(35) . . . yes C9 C11 H11B 111.2(50) . . . yes H11A C11 H11B 109.2(60) . . . yes O1 C14 H14A 116.9(70) . . . yes O1 C14 H14B 107.8(95) . . . yes O1 C14 H14C 108.0(7) . . . yes H14A C14 H14B 107.6(118) . . . yes H14A C14 H14C 107.5(70) . . . yes H14B C14 H14C 108.9(94) . . . yes O2 C15 H15A 117.6(10) . . . yes O2 C15 H15B 107.5(10) . . . yes O2 C15 H15C 107.2(9) . . . yes H15A C15 H15B 107.7(11) . . . yes H15A C15 H15C 107.6(11) . . . yes H15B C15 H15C 109.0(11) . . . yes C16 C17 H17A 112.0(13) . . . yes C16 C17 H17B 108.9(10) . . . yes C16 C17 H17C 108.5(11) . . . yes H17A C17 H17B 109.1(13) . . . yes H17A C17 H17C 109.3(12) . . . yes H17B C17 H17C 109.0(14) . . . yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C15 3.36(1) 1_555 6_556 ? O4 C9 3.279(8) 1_555 2_657 ? O4 C11 3.284(9) 1_555 2_657 ? O4 H17A 2.519(5) 1_555 1_545 ? C5 C5 3.235(8) 1_555 5_656 ? C5 C7 3.082(8) 1_555 5_656 ? C5 C9 2.543(9) 1_555 5_656 ? C5 C11 3.875(9) 1_555 5_656 ? C5 H9 2.58(6) 1_555 5_656 ? C6 C6 2.987(9) 1_555 5_656 ? C6 C7 2.543(8) 1_555 5_656 ? C6 C8 3.894(9) 1_555 5_656 ? C6 C9 3.131(9) 1_555 5_656 ? C6 O10 2.960(9) 1_555 5_656 ? C6 C11 3.950(9) 1_555 5_656 ? C6 C13 2.541(9) 1_555 5_656 ? C6 C14 3.83(1) 1_555 2_555 ? C6 H14A 3.1(1) 1_555 2_555 ? C7 C7 3.465(8) 1_555 5_656 ? C7 C9 3.437(9) 1_555 5_656 ? C8 H17A 3.198(6) 1_555 1_545 ? C9 C9 3.786(9) 1_555 5_656 ? C9 C13 3.360(9) 1_555 5_656 ? O10 C17 3.34(2) 1_555 6_546 ? O10 H14B 2.5(2) 1_555 6_555 ? O12 C14 3.35(1) 1_555 3_557 ? O12 C16 3.26(1) 1_555 2_667 ? C13 H9 3.05(6) 1_555 5_656 ? C14 C14 3.97(1) 1_555 3_547 ? C14 H15A 3.183(9) 1_555 6_556 ? C15 C17 3.91(2) 1_555 1_545 ? C16 C16 3.75(1) 1_555 2_667 ? O1 C15 3.36(1) 1_555 6_556 ? O4 C9 3.279(8) 1_555 2_657 ? O4 C11 3.284(9) 1_555 2_657 ? O4 H17A 2.519(5) 1_555 1_545 ? C5 C5 3.235(8) 1_555 5_656 ? C5 C7 3.082(8) 1_555 5_656 ? C5 C9 2.543(9) 1_555 5_656 ? C5 C11 3.875(9) 1_555 5_656 ? C5 H9 2.58(6) 1_555 5_656 ? C6 C6 2.987(9) 1_555 5_656 ? C6 C7 2.543(8) 1_555 5_656 ? C6 C8 3.894(9) 1_555 5_656 ? C6 C9 3.131(9) 1_555 5_656 ? C6 O10 2.960(9) 1_555 5_656 ? C6 C11 3.950(9) 1_555 5_656 ? C6 C13 2.541(9) 1_555 5_656 ? C6 C14 3.83(1) 1_555 2_555 ? C6 H14A 3.1(1) 1_555 2_555 ? C7 C7 3.465(8) 1_555 5_656 ? C7 C9 3.437(9) 1_555 5_656 ? C8 H17A 3.198(6) 1_555 1_545 ? C9 C9 3.786(9) 1_555 5_656 ? C9 C13 3.360(9) 1_555 5_656 ? O10 C17 3.34(2) 1_555 6_546 ? O10 H14B 2.5(2) 1_555 6_555 ? O12 C14 3.35(1) 1_555 3_557 ? O12 C16 3.26(1) 1_555 2_667 ? C13 H9 3.05(6) 1_555 5_656 ? C14 C14 3.97(1) 1_555 3_547 ? C14 H15A 3.183(9) 1_555 6_556 ? C15 C17 3.91(2) 1_555 1_545 ? C16 C16 3.75(1) 1_555 2_667 ? #===================================================END