# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/396 data_2a # CHEMICAL DATA _chemical_name_systematic ; (3R^*^,1'S^*^)-2-(1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2,4-dimethyl- pentan-3-ol ; _chemical_formula_sum ' C15 H22 O2 ' _chemical_formula_weight 234.37 # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M ' P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z ' ' 1/2-x, -y, 1/2+z ' ' 1/2+x, 1/2-y, -z ' ' -x, 1/2+y, 1/2-z ' _cell_length_a 7.8840(5) _cell_length_b 12.514(1) _cell_length_c 14.297(1) _cell_angle_alpha 90.00(0) _cell_angle_beta 90.00(0) _cell_angle_gamma 90.00(0) _cell_volume 1410.6(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used all _cell_measurement_temperature 298 _exptl_crystal_description ' cube ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.103 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type ' none ' # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo Ka' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device ' MacScience DIP3000 ' _diffrn_measurement_method 'area detector' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13456 _diffrn_reflns_total 2087 _diffrn_reflns_theta_max ' 28.91 ' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 # REFINMENT DATA _reflns_number_total 2087 _reflns_number_observed 1747 _reflns_observed_criterion 'I>sigma(I)' _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.062 _refine_ls_hydrogen_treatment ' refxyz ' _refine_ls_number_reflns 1747 _refine_ls_number_parameters 242 _refine_ls_goodness_of_fit_ref 1.276 _refine_ls_weighting_scheme calc _refine_ls_shift/su_max 5.3552 _refine_diff_density_min -0.15 _refine_diff_density_max 0.18 _refine_ls_extinction_method none _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'least squares' # 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 O1 -0.16518(5) 0.27806(3) 1.07146(2) 0.0608(1) O2 -0.34365(5) 0.15643(3) 0.96395(2) 0.0617(1) C1 -0.14015(5) 0.01192(3) 0.99713(2) 0.0495(1) C2 0.03120(6) 0.01916(3) 0.97739(3) 0.0583(2) C3 0.10847(7) -0.07465(4) 0.94451(4) 0.0678(2) C4 0.01706(8) -0.16928(4) 0.93408(3) 0.0668(2) C5 -0.15469(8) -0.17557(3) 0.95319(3) 0.0638(2) C6 -0.23110(6) -0.08199(3) 0.98357(3) 0.0558(2) C7 -0.39982(7) -0.03076(4) 1.00642(4) 0.0648(2) C8 -0.29623(5) 0.07461(3) 1.02823(3) 0.0512(1) C9 -0.29753(6) 0.11617(3) 1.13072(3) 0.0544(1) C10 -0.15006(6) 0.19763(3) 1.14285(3) 0.0524(1) C11 -0.13141(9) 0.24768(4) 1.24102(3) 0.0702(2) C12 -0.1971(2) 0.3610(1) 1.2481(1) 0.1116(6) C13 -0.47124(8) 0.16606(5) 1.15132(4) 0.0704(2) C14 -0.26380(9) 0.02283(4) 1.19847(4) 0.0720(2) C15 0.05267(16) 0.24550(10) 1.27267(6) 0.1020(5) H10 -0.0489(11) 0.1550(6) 1.1300(5) 0.056(1) H3 0.2178(15) -0.0730(8) 0.9306(7) 0.071(2) H5 -0.2037(16) -0.2458(9) 0.9527(7) 0.079(2) H2 0.0939(13) 0.0887(7) 0.9866(6) 0.096(2) H14A -0.2645(19) 0.0439(11) 1.2571(9) 0.095(3) H7A -0.4624(16) -0.0684(9) 1.0549(8) 0.083(2) H4 0.0738(14) -0.2325(9) 0.9119(7) 0.077(2) H13A -0.4882(13) 0.2381(8) 1.1166(7) 0.073(2) H2 -0.28425 0.21344 0.97918 0.069 H14B -0.337(2) -0.034(1) 1.190(1) 0.109(4) H7B -0.4671(13) -0.0215(7) 0.9515(6) 0.065(2) H14C -0.150(3) -0.018(1) 1.178(1) 0.111(4) H13B -0.5700(19) 0.1220(10) 1.1371(8) 0.091(3) H13C -0.4683(18) 0.1822(10) 1.2190(8) 0.093(3) H12A -0.179(3) 0.384(2) 1.311(1) 0.129(5) H11 -0.193(2) 0.199(1) 1.287(1) 0.114(4) H12B -0.126(2) 0.410(1) 1.201(1) 0.105(4) H12C -0.303(2) 0.361(1) 1.228(1) 0.100(4) H1 -0.0661(17) 0.3083(10) 1.0658(8) 0.083(2) H15A 0.066(3) 0.273(1) 1.345(1) 0.128(5) H15B 0.121(3) 0.295(2) 1.230(2) 0.151(7) H15C 0.133(3) 0.167(2) 1.271(2) 0.146(6) 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 0.0585(2) 0.0606(2) 0.0632(2) -.0090(1) 0.0060(1) 0.0149(1) O2 0.0555(2) 0.0677(2) 0.0619(1) 0.0081(1) -.0093(1) 0.0124(1) C1 0.0476(2) 0.0461(1) 0.0547(1) -.0048(1) -.0058(1) 0.0038(1) C2 0.0464(2) 0.0532(2) 0.0754(2) -.0030(1) -.0046(2) -.0006(2) C3 0.0551(3) 0.0669(2) 0.0813(3) 0.0071(2) 0.0009(2) -.0030(2) C4 0.0791(3) 0.0559(2) 0.0654(2) 0.0098(2) -.0075(2) -.0008(2) C5 0.0847(3) 0.0506(2) 0.0560(2) -.0108(2) -.0075(2) -.0009(1) C6 0.0590(2) 0.0537(2) 0.0547(2) -.0108(1) -.0067(1) 0.0004(1) C7 0.0488(2) 0.0686(2) 0.0768(3) -.0139(2) -.0078(2) 0.0003(2) C8 0.0446(2) 0.0515(2) 0.0573(2) -.0021(1) -.0044(1) 0.0056(1) C9 0.0571(2) 0.0506(2) 0.0556(2) -.0014(1) 0.0024(1) 0.0095(1) C10 0.0522(2) 0.0519(2) 0.0531(1) -.0005(1) -.0009(1) 0.0040(1) C11 0.0915(4) 0.0640(2) 0.0552(2) -.0128(2) 0.0028(2) -.0018(2) C12 0.149(1) 0.086(0) 0.100(0) 0.024(1) -0.010(1) -0.032(0) C13 0.0564(3) 0.0798(3) 0.0751(3) 0.0010(2) 0.0143(2) 0.0047(2) C14 0.0934(4) 0.0588(2) 0.0640(2) -.0069(2) -.0043(2) 0.0166(2) C15 0.1083(7) 0.1161(6) 0.0815(4) -.0048(5) -.0323(4) -.0148(4) # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C10 1.438(1) O2 C8 1.426(1) C1 C2 1.383(1) C1 C6 1.390(1) C1 C8 1.526(1) C2 C3 1.404(1) C3 C4 1.394(1) C4 C5 1.384(1) C5 C6 1.387(1) C6 C7 1.512(1) C7 C8 1.582(1) C8 C9 1.555(1) C9 C10 1.556(1) C9 C13 1.534(1) C9 C14 1.541(1) C10 C11 1.544(1) C11 C12 1.513(2) C11 C15 1.520(2) O1 H1 0.871(14) O2 H2 0.881(1) C2 H2 1.010(10) C3 H3 0.885(12) C4 H4 0.962(11) C5 H5 0.960(12) C7 H7A 0.972(12) C7 H7B 0.954(9) C10 H10 0.977(9) C11 H11 1.016(18) C12 H12A 0.96(2) C12 H12B 1.063(16) C12 H12C 0.879(19) C13 H13A 1.037(10) C13 H13B 0.975(14) C13 H13C 0.988(12) C14 H14A 0.879(14) C14 H14B 0.924(17) C14 H14C 1.073(19) C15 H15A 1.091(19) C15 H15B 1.02(3) C15 H15C 1.17(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 122.1(1) C2 C1 C8 144.5(1) C6 C1 C8 93.4(1) C1 C2 C3 115.9(1) C2 C3 C4 121.5(1) C3 C4 C5 122.2(1) C4 C5 C6 116.0(1) C1 C6 C5 122.2(1) C1 C6 C7 93.7(1) C5 C6 C7 143.9(1) C6 C7 C8 86.7(1) O2 C8 C1 113.1(1) O2 C8 C7 109.6(1) O2 C8 C9 111.4(1) C1 C8 C7 86.0(1) C1 C8 C9 116.9(1) C7 C8 C9 117.5(1) C8 C9 C10 108.6(1) C8 C9 C13 108.8(1) C8 C9 C14 109.7(1) C10 C9 C13 112.3(1) C10 C9 C14 107.3(1) C13 C9 C14 110.0(1) O1 C10 C9 108.5(1) O1 C10 C11 111.7(1) C9 C10 C11 116.0(1) C10 C11 C12 114.1(1) C10 C11 C15 110.7(1) C12 C11 C15 108.9(1) C10 O1 H1 107.2(8) C8 O2 H2 106.4(1) C1 C2 H2 120.5(6) C3 C2 H2 123.5(6) C2 C3 H3 118.6(7) C4 C3 H3 120.0(7) C3 C4 H4 119.5(7) C5 C4 H4 118.2(7) C4 C5 H5 116.4(8) C6 C5 H5 126.9(8) C6 C7 H7A 113.2(7) C6 C7 H7B 111.2(6) C8 C7 H7A 121.7(7) C8 C7 H7B 110.4(6) H7A C7 H7B 111.3(9) O1 C10 H10 108.5(5) C9 C10 H10 103.4(5) C11 C10 H10 108.3(5) C10 C11 H11 107.1(10) C12 C11 H11 111.1(10) C15 C11 H11 104.5(11) C11 C12 H12A 107.0(12) C11 C12 H12B 108.6(9) C11 C12 H12C 107.5(10) H12A C12 H12B 109.8(15) H12A C12 H12C 116.6(17) H12B C12 H12C 107.2(14) C9 C13 H13A 112.1(6) C9 C13 H13B 116.3(8) C9 C13 H13C 104.5(9) H13A C13 H13B 106.8(10) H13A C13 H13C 107.1(10) H13B C13 H13C 109.8(11) C9 C14 H14A 111.8(9) C9 C14 H14B 113.7(11) C9 C14 H14C 109.8(9) H14A C14 H14B 110.3(14) H14A C14 H14C 113.8(14) H14B C14 H14C 96.7(14) C11 C15 H15A 111.4(13) C11 C15 H15B 108.3(15) C11 C15 H15C 121.9(12) H15A C15 H15B 108.4(18) H15A C15 H15C 103.6(16) H15B C15 H15C 102.3(18) data_2f # CHEMICAL DATA _chemical_name_systematic ; (2S^*^,1'S^*^)-2-Acetoxy-3-(1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-3 -methylbutane ; _chemical_formula_sum ' C15 H20 O3 ' _chemical_formula_weight 248.32 # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P 21/n ' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z ' ' -x, 1/2+y, 1/2-z ' _cell_length_a 11.308(2) _cell_length_b 9.460(1) _cell_length_c 13.187(1) _cell_angle_alpha 90.00(0) _cell_angle_beta 96.191(8) _cell_angle_gamma 90.00(0) _cell_volume 1402.4(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used all _cell_measurement_temperature 298 _exptl_crystal_description ' cube ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type ' none ' # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo Ka' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device ' MacScience DIP3000 ' _diffrn_measurement_method 'area detector' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13456 _diffrn_reflns_total 3578 _diffrn_reflns_theta_max ' 28.83 ' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 # REFINMENT DATA _reflns_number_total 3578 _reflns_number_observed 1920 _reflns_observed_criterion 'I>3sigma(I)' _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.067 _refine_ls_hydrogen_treatment ' refxyz ' _refine_ls_number_reflns 1920 _refine_ls_number_parameters 243 _refine_ls_goodness_of_fit_ref 1.604 _refine_ls_weighting_scheme calc _refine_ls_shift/su_max 0.0459 _refine_diff_density_min -0.14 _refine_diff_density_max 0.23 _refine_ls_extinction_method none _atoms_sites_solution_primary ' direct methods' _atoms_sites_solution_secondary 'least squares' # 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 O1 0.85937(5) 0.11710(5) 0.65562(4) 0.0582(2) O2 0.83944(4) 0.21751(5) 0.87964(4) 0.0522(2) O3 0.94554(5) 0.41683(6) 0.87335(5) 0.0669(3) C1 0.79596(7) -0.18631(8) 0.72534(6) 0.0596(3) C2 0.79145(9) -0.33219(9) 0.71454(8) 0.0730(4) C3 0.72344(10) -0.38238(9) 0.63018(9) 0.0814(5) C4 0.66057(8) -0.29380(9) 0.55894(8) 0.0724(4) C5 0.66604(7) -0.14721(8) 0.57003(6) 0.0624(4) C6 0.73452(6) -0.09698(7) 0.65557(5) 0.0532(3) C7 0.78245(5) 0.03673(7) 0.71094(5) 0.0489(3) C8 0.85142(7) -0.06720(8) 0.79237(6) 0.0575(3) C9 0.68983(6) 0.13864(7) 0.74785(5) 0.0507(3) C10 0.75177(5) 0.26938(7) 0.79969(5) 0.0489(3) C11 0.93187(6) 0.30077(7) 0.90913(5) 0.0524(3) C12 1.01460(8) 0.23460(11) 0.99081(7) 0.0690(4) C13 0.61398(8) 0.06181(10) 0.82033(8) 0.0714(4) C14 0.61023(8) 0.19045(10) 0.65400(7) 0.0682(4) C15 0.67043(8) 0.37110(10) 0.84825(7) 0.0680(4) H1 0.9126(10) 0.0614(13) 0.6363(8) 0.075(3) H2 0.8307(12) -0.3913(14) 0.7542(10) 0.090(3) H3 0.7204(11) -0.4797(13) 0.6187(8) 0.080(3) H4 0.6069(12) -0.3347(15) 0.4972(10) 0.095(4) H5 0.6230(12) -0.0839(14) 0.5186(10) 0.093(3) H8A 0.8246(8) -0.0614(9) 0.8608(7) 0.054(2) H8B 0.9412(9) -0.0570(10) 0.7949(7) 0.065(2) H10 0.7952(7) 0.3197(9) 0.7521(6) 0.046(2) H12A 1.0369(16) 0.1567(20) 0.9601(14) 0.127(5) H12B 0.9816(17) 0.2071(19) 1.0516(15) 0.133(5) H12C 1.0790(16) 0.2954(18) 1.0130(13) 0.119(5) H13A 0.5921(11) -0.0333(14) 0.7957(9) 0.085(3) H13B 0.6537(11) 0.0549(12) 0.8906(10) 0.078(3) H13C 0.5403(12) 0.1214(13) 0.8206(9) 0.088(3) H14A 0.5715(10) 0.1117(11) 0.6204(8) 0.071(3) H14B 0.6573(12) 0.2287(12) 0.6050(10) 0.083(3) H14C 0.5507(13) 0.2559(14) 0.6746(10) 0.095(4) H15A 0.6360(12) 0.3293(13) 0.9034(9) 0.084(3) H15B 0.7199(11) 0.4531(14) 0.8804(9) 0.084(3) H15C 0.6077(12) 0.4105(13) 0.7972(10) 0.089(3) 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 0.0559(3) 0.0502(2) 0.0692(3) 0.0016(2) 0.0193(2) 0.0095(2) O2 0.0508(2) 0.0500(2) 0.0544(2) 0.0008(2) -.0013(2) 0.0091(2) O3 0.0538(3) 0.0579(3) 0.0873(4) -.0079(2) -.0003(3) 0.0076(3) C1 0.0621(4) 0.0485(3) 0.0671(4) 0.0022(3) 0.0049(3) 0.0119(3) C2 0.0857(5) 0.0467(4) 0.0851(5) 0.0023(3) 0.0050(4) 0.0164(4) C3 0.0900(6) 0.0493(4) 0.1045(7) -.0134(4) 0.0187(5) -.0003(4) C4 0.0680(5) 0.0657(5) 0.0827(5) -.0128(3) 0.0081(4) -.0098(4) C5 0.0630(4) 0.0622(4) 0.0606(4) -.0030(3) 0.0010(3) 0.0007(3) C6 0.0516(3) 0.0482(3) 0.0590(3) -.0014(2) 0.0043(3) 0.0082(3) C7 0.0442(3) 0.0459(3) 0.0553(3) -.0004(2) -.0002(2) 0.0095(3) C8 0.0573(3) 0.0539(3) 0.0593(3) 0.0066(3) -.0063(3) 0.0144(3) C9 0.0414(3) 0.0531(3) 0.0568(3) -.0005(2) 0.0022(2) 0.0042(3) C10 0.0421(3) 0.0489(3) 0.0549(3) 0.0032(2) -0.0028(2) 0.0082(3) C11 0.0460(3) 0.0539(3) 0.0564(3) 0.0030(2) 0.0021(2) -.0019(3) C12 0.0612(4) 0.0773(5) 0.0660(4) 0.0105(4) -.0095(3) -.0026(4) C13 0.0571(4) 0.0751(5) 0.0827(5) -.0138(3) 0.0221(4) 0.0018(4) C14 0.0588(4) 0.0712(5) 0.0712(5) 0.0171(4) -.0171(4) -.0028(4) C15 0.0602(4) 0.0682(4) 0.0754(5) 0.0093(3) 0.0132(4) -.0058(4) # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.416(1) O2 C10 1.452(1) O2 C11 1.333(1) O3 C11 1.211(1) C1 C2 1.388(2) C1 C6 1.380(2) C1 C8 1.525(2) C2 C3 1.367(2) C3 C4 1.395(2) C4 C5 1.395(2) C5 C6 1.382(2) C6 C7 1.530(1) C7 C8 1.596(2) C7 C9 1.541(1) C9 C10 1.544(1) C9 C13 1.534(2) C9 C14 1.530(2) C10 C15 1.520(2) C11 C12 1.487(2) O1 H1 0.859(12) C2 H2 0.856(14) C3 H3 0.933(13) C4 H4 1.036(14) C5 H5 0.993(14) C8 H8A 0.984(9) C8 H8B 1.017(11) C10 H10 0.963(8) C12 H12A 0.890(19) C12 H12B 0.96(2) C12 H12C 0.949(18) C13 H13A 0.979(14) C13 H13B 0.988(13) C13 H13C 1.007(14) C14 H14A 0.950(11) C14 H14B 0.952(13) C14 H14C 0.974(14) C15 H15A 0.948(13) C15 H15B 1.021(13) C15 H15C 0.996(14) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 O2 C11 117.7(1) C2 C1 C6 122.0(1) C2 C1 C8 143.4(1) C6 C1 C8 94.6(1) C1 C2 C3 116.1(1) C2 C3 C4 122.7(1) C3 C4 C5 120.9(1) C4 C5 C6 116.2(1) C1 C6 C5 122.1(1) C1 C6 C7 93.5(1) C5 C6 C7 144.3(1) O1 C7 C6 113.8(1) O1 C7 C8 113.3(1) O1 C7 C9 107.6(1) C6 C7 C8 86.2(1) C6 C7 C9 116.8(1) C8 C7 C9 118.2(1) C1 C8 C7 85.7(1) C7 C9 C10 110.5(1) C7 C9 C13 110.2(1) C7 C9 C14 107.8(1) C10 C9 C13 111.2(1) C10 C9 C14 107.5(1) C13 C9 C14 109.6(1) O2 C10 C9 107.0(1) O2 C10 C15 107.7(1) C9 C10 C15 115.3(1) O2 C11 O3 123.4(1) O2 C11 C12 112.0(1) O3 C11 C12 124.5(1) C7 O1 H1 108.2(8) C1 C2 H2 125.2(9) C3 C2 H2 118.6(9) C2 C3 H3 118.8(8) C4 C3 H3 118.5(8) C3 C4 H4 121.2(8) C5 C4 H4 118.0(8) C4 C5 H5 121.0(8) C6 C5 H5 122.7(8) C1 C8 H8A 115.1(6) C1 C8 H8B 115.9(6) C7 C8 H8A 114.0(6) C7 C8 H8B 112.2(6) H8A C8 H8B 111.7(8) O2 C10 H10 106.5(5) C9 C10 H10 110.2(5) C15 C10 H10 109.6(5) C11 C12 H12A 101.9(12) C11 C12 H12B 116.8(12) C11 C12 H12C 111.7(11) H12A C12 H12B 108.2(17) H12A C12 H12C 113.4(16) H12B C12 H12C 105.1(16) C9 C13 H13A 111.5(8) C9 C13 H13B 112.8(8) C9 C13 H13C 104.8(8) H13A C13 H13B 108.9(10) H13A C13 H13C 109.6(11) H13B C13 H13C 109.1(10) C9 C14 H14A 109.2(7) C9 C14 H14B 110.3(8) C9 C14 H14C 110.0(8) H14A C14 H14B 104.2(10) H14A C14 H14C 109.3(11) H14B C14 H14C 113.6(11) C10 C15 H15A 112.1(8) C10 C15 H15B 109.1(8) C10 C15 H15C 111.8(8) H15A C15 H15B 104.5(10) H15A C15 H15C 110.7(11) H15B C15 H15C 108.3(11) data_3 _chemical_name_systematic ; (3S^*^,1'R^*^)-3-Acetoxy-2-(1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2 ,4-dimethylpentane ; _chemical_formula_sum ' C17 H24 O3 ' _chemical_formula_weight 276.38 # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P 21/n ' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z ' ' -x, 1/2+y, 1/2-z ' _cell_length_a 10.106(1) _cell_length_b 25.218(2) _cell_length_c 12.298(2) _cell_angle_alpha 90.00(0) _cell_angle_beta 90.176(5) _cell_angle_gamma 90.00(0) _cell_volume 3134.2(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used all _cell_measurement_temperature 298 _exptl_crystal_description ' cube ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ' none ' # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo Ka' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device ' MacScience DIP3000 ' _diffrn_measurement_method 'area detector' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 30159 _diffrn_reflns_total 6743 _diffrn_reflns_theta_max ' 28.46 ' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 # REFINMENT DATA _reflns_number_total 8447 _reflns_number_observed 2941 _reflns_observed_criterion 'I>3sigma(I)' _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_ref 0.071 _refine_ls_hydrogen_treatment ' refxyz ' _refine_ls_number_reflns 2941 _refine_ls_number_parameters 415 _refine_ls_goodness_of_fit_ref 2.364 _refine_ls_weighting_scheme calc _refine_ls_shift/su_max 0.0404 _refine_diff_density_min -0.24 _refine_diff_density_max 0.22 _refine_ls_extinction_method none _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'least squares' # 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 C1 0.57230(14) 0.44060(5) 0.12420(12) 0.0501(7) C2 0.67090(14) 0.45310(5) 0.19900(12) 0.0546(7) C3 0.67980(16) 0.42680(6) 0.29770(14) 0.0624(8) C4 0.59440(15) 0.38620(6) 0.32630(13) 0.0599(8) C5 0.49640(19) 0.37370(6) 0.25140(16) 0.0477(9) C6 0.48630(18) 0.40020(6) 0.15340(16) 0.0404(9) C7 0.36800(19) 0.36730(7) 0.11490(17) 0.0395(9) C8 0.3806(2) 0.3369(1) 0.2271(2) 0.048(1) C9 0.2360(2) 0.3972(1) 0.0926(2) 0.038(1) C10 0.1206(2) 0.3562(1) 0.0847(2) 0.040(1) C11 -0.0236(2) 0.3761(1) 0.0971(2) 0.048(1) C12 -0.06690(19) 0.41690(8) 0.01370(17) 0.0588(9) C13 -0.1190(2) 0.3291(1) 0.0949(2) 0.0717(9) C14 0.1614(2) 0.2788(1) -0.0234(2) 0.047(1) C15 0.1802(2) 0.2606(1) -0.1369(2) 0.0789(9) C16 0.2076(2) 0.4347(1) 0.1884(2) 0.055(1) C17 0.2541(2) 0.4296(1) -0.0114(2) 0.052(1) C18 0.2545(2) 0.1269(1) 0.2473(2) 0.047(1) C19 0.1585(2) 0.1130(1) 0.3229(2) 0.062(1) C20 0.0749(2) 0.0717(1) 0.2927(2) 0.067(1) C21 0.0874(2) 0.0462(1) 0.1957(2) 0.062(1) C22 0.1838(2) 0.0593(1) 0.1200(2) 0.052(1) C23 0.2670(3) 0.1007(1) 0.1488(2) 0.045(1) C24 0.3838(3) 0.1347(1) 0.1125(2) 0.040(1) C25 0.3696(2) 0.1639(1) 0.2256(2) 0.053(1) C26 0.51660(19) 0.10490(7) 0.09030(17) 0.0367(9) C27 0.6314(2) 0.1460(1) 0.0852(2) 0.0388(9) C28 0.7751(2) 0.1261(1) 0.0997(2) 0.052(1) C30 0.8196(2) 0.0850(1) 0.0173(2) 0.0620(9) C31 0.5913(2) 0.2240(1) -0.0232(2) 0.047(1) C32 0.5736(2) 0.2420(1) -0.1372(2) 0.080(1) C33 0.5438(3) 0.0657(1) 0.1828(3) 0.052(1) C34 0.4984(2) 0.0744(1) -0.0172(2) 0.048(1) C38 0.8701(2) 0.1733(1) 0.0983(2) 0.074(1) H1 0.5640(2) 0.4587(1) 0.0559(3) 0.052(1) H1 0.45200 0.31840 0.04570 0.052 H2 0.7331(4) 0.4807(1) 0.1823(3) 0.094(2) H3 0.7487(3) 0.4367(1) 0.3477(3) 0.080(1) H4 0.6009(3) 0.3677(1) 0.3944(3) 0.050(1) H4 0.29360 0.18600 0.04420 0.045 H8A 0.30640 0.34040 0.27510 0.07(1) H8B 0.40310 0.30000 0.22090 0.041(7) H10 0.12960 0.33040 0.14170 0.057(7) H11 -0.03170 0.39200 0.16760 0.04(1) H12A -0.15590 0.42950 0.02170 0.106(6) H12B -0.05880 0.40090 -0.05680 0.081(8) H12C -0.00810 0.44670 0.01810 0.093(8) H13A -0.20810 0.34170 0.10290 0.110(7) H13B -0.09740 0.30540 0.15330 0.102(7) H13C -0.10990 0.31070 0.02710 0.075(8) H15A 0.20410 0.22380 -0.13930 0.134(7) H15B 0.24950 0.28120 -0.16920 0.166(6) H15C 0.10010 0.26580 -0.17770 0.17(1) H16A 0.12650 0.45340 0.17410 0.08(1) H16B 0.27890 0.45960 0.19700 0.07(1) H16C 0.19930 0.41430 0.25390 0.08(1) H17A 0.17310 0.44830 -0.02570 0.09(1) H17B 0.27410 0.40640 -0.07100 0.05(1) H17C 0.32530 0.45450 -0.00250 0.058(7) H19 0.15120 0.13100 0.39150 0.083(4) H20 0.00580 0.06150 0.34180 0.10(2) H21 0.02830 0.01740 0.17980 0.05(3) H22 0.19260 0.04160 0.05140 0.06(2) H25A 0.443(3) 0.160(1) 0.274(2) 0.047(6) H25B 0.34660 0.20080 0.22070 0.067(9) H27 0.60930 0.17060 0.14180 0.03(1) H28 0.782(3) 0.110(1) 0.171(2) 0.054(8) H30A 0.90860 0.07250 0.02700 0.090(9) H30B 0.81270 0.10070 -0.05360 0.091(6) H30C 0.76080 0.05520 0.02130 0.095(9) H32A 0.54890 0.27880 -0.13970 0.133(8) H32B 0.50550 0.22110 -0.17090 0.21(1) H32C 0.65470 0.23710 -0.17630 0.17(1) H33A 0.55490 0.08500 0.24950 0.062(6) H33B 0.62230 0.04560 0.16790 0.061(7) H33C 0.47020 0.04190 0.18920 0.047(7) H34A 0.42790 0.04890 -0.01500 0.07(2) H34B 0.57950 0.05610 -0.03300 0.06(2) H34C 0.48020 0.09920 -0.07440 0.06(2) H38A 0.95900 0.16070 0.10790 0.106(5) H38B 0.84790 0.19750 0.15560 0.10(1) H38C 0.86210 0.19120 0.02970 0.093(9) O1 0.39520 0.33580 0.02170 0.048 O2 0.12780 0.33020 -0.02030 0.041 O3 0.17330 0.25120 0.05600 0.062 O4 0.35630 0.16700 0.02090 0.047 O5 0.62530 0.17280 -0.01990 0.042 O6 0.57890 0.25160 0.05580 0.063 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 C1 0.0405(8) 0.0552(7) 0.0545(8) -.0005(6) 0.0064(6) -.0060(6) C2 0.0406(8) 0.0620(7) 0.0613(8) -.0032(6) 0.0058(6) -.0140(6) C3 0.0380(9) 0.0847(8) 0.0644(10) 0.0026(7) -.0075(7) -.0247(7) C4 0.0527(8) 0.0845(8) 0.0425(10) 0.0074(7) -.0089(7) -.0001(7) C5 0.043(1) 0.058(1) 0.043(1) 0.008(1) -0.003(1) 0.000(1) C6 0.035(1) 0.045(1) 0.042(1) 0.003(1) 0.003(1) -0.007(1) C7 0.039(1) 0.043(1) 0.036(1) 0.000(1) 0.002(1) -0.004(1) C8 0.050(1) 0.046(1) 0.050(1) 0.004(1) -0.002(1) 0.004(1) C9 0.032(1) 0.037(1) 0.045(1) -0.003(1) 0.001(1) -0.003(1) C10 0.043(1) 0.042(1) 0.035(1) 0.000(1) -0.002(1) 0.000(1) C11 0.040(1) 0.055(1) 0.049(1) -0.006(1) 0.004(1) -0.006(1) C12 0.043(1) 0.064(1) 0.068(1) 0.012(1) 0.001(1) 0.001(1) C13 0.048(1) 0.073(1) 0.094(1) -0.012(1) 0.005(1) 0.004(1) C14 0.040(1) 0.041(1) 0.060(2) 0.002(1) -0.011(1) -0.004(1) C15 0.104(1) 0.065(1) 0.067(1) 0.024(1) -0.020(1) -0.023(1) C16 0.042(1) 0.056(1) 0.066(1) -0.001(1) 0.004(1) -0.023(1) C17 0.047(1) 0.049(1) 0.060(1) 0.004(1) 0.001(1) 0.011(1) C18 0.044(1) 0.056(1) 0.042(1) 0.005(1) 0.005(1) 0.005(1) C19 0.052(1) 0.080(1) 0.053(1) 0.010(1) 0.007(1) 0.016(1) C20 0.045(1) 0.089(1) 0.067(1) 0.006(1) 0.009(1) 0.030(1) C21 0.041(1) 0.061(1) 0.085(1) -0.010(1) -0.011(1) 0.028(1) C22 0.042(1) 0.053(1) 0.059(2) -0.007(1) -0.005(1) 0.009(1) C23 0.038(1) 0.048(2) 0.050(2) 0.001(1) 0.000(1) 0.012(1) C24 0.041(1) 0.035(2) 0.046(1) 0.002(1) 0.002(1) 0.003(1) C25 0.054(1) 0.051(1) 0.053(2) 0.005(1) 0.004(1) -0.008(1) C26 0.034(1) 0.038(1) 0.039(1) 0.002(1) -0.003(1) 0.002(1) C27 0.040(1) 0.040(1) 0.037(1) -0.002(1) 0.001(1) 0.001(1) C28 0.042(1) 0.063(1) 0.051(1) 0.000(1) -0.006(1) 0.005(1) C30 0.044(1) 0.074(1) 0.068(1) 0.015(1) -0.001(1) 0.005(1) C31 0.043(1) 0.038(1) 0.060(2) 0.001(1) 0.012(1) 0.006(1) C32 0.100(1) 0.063(1) 0.076(2) 0.023(1) 0.015(1) 0.024(1) C33 0.050(1) 0.055(2) 0.051(2) 0.007(1) 0.001(1) 0.020(2) C34 0.053(1) 0.042(1) 0.049(2) 0.004(1) -0.002(1) -0.005(1) C38 0.042(1) 0.084(2) 0.096(2) -0.016(1) -0.001(1) -0.001(1) O1 0.04(1) 0.05 0.05 0.01 0.00 -0.01 O2 0.05(1) 0.04 0.04 0.00 -0.01 0.00 O3 0.07(1) 0.04 0.07 0.01 0.00 0.01 O4 0.041(9) 0.047 0.051 0.008 0.004 0.016 O5 0.0440 0.0381 0.0449 0.0050 0.0073 0.0034 O6 0.0679 0.0449 0.0763 0.0076 -.0022 -.0139 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.390(3) C1 C6 1.387(3) C2 C3 1.386(3) C3 C4 1.385(3) C4 C5 1.387(3) C5 C6 1.382(3) C5 C8 1.522(3) C6 C7 1.529(3) C7 C8 1.583(4) C7 C9 1.556(3) C7 O1 1.422(2) C9 C10 1.561(4) C9 C16 1.538(4) C9 C17 1.529(4) C10 C11 1.549(4) C10 O2 1.450(3) C11 C12 1.516(4) C11 C13 1.528(3) C14 C15 1.482(4) C14 O2 1.341(3) C14 O3 1.205(3) C18 C19 1.391(4) C18 C23 1.386(4) C18 C25 1.516(4) C19 C20 1.391(4) C20 C21 1.361(4) C21 C22 1.389(4) C22 C23 1.386(4) C23 C24 1.527(4) C24 C25 1.581(4) C24 C26 1.563(4) C24 O4 1.417(3) C26 C27 1.557(3) C26 C33 1.531(4) C26 C34 1.540(4) C27 C28 1.546(4) C27 O5 1.460(3) C28 C30 1.519(4) C28 C38 1.529(4) C31 C32 1.484(4) C31 O5 1.337(3) C31 O6 1.202(3) C1 H1 0.959(4) C2 H2 0.960(4) C3 H3 0.961(4) C4 H4 0.961(4) C8 H8B 0.961(3) C8 H8A 0.960(3) C11 H11 0.959(3) C10 H10 0.961(3) C12 H12B 0.960(3) C12 H12A 0.959(2) C13 H13A 0.960(2) C12 H12C 0.959(2) C13 H13C 0.959(3) C13 H13B 0.959(2) C15 H15B 0.959(2) C15 H15A 0.959(2) C16 H16A 0.961(3) C15 H15C 0.960(3) C16 H16C 0.960(3) C16 H16B 0.961(3) C17 H17B 0.960(3) C17 H17A 0.960(3) C19 H19 0.961(3) C17 H17C 0.961(3) C21 H21 0.960(3) C20 H20 0.960(3) C25 H25A 0.96(3) C22 H22 0.959(3) C27 H27 0.959(3) C25 H25B 0.961(3) C30 H30A 0.960(3) C28 H28 0.96(3) C30 H30C 0.959(3) C30 H30B 0.960(3) C32 H32B 0.960(3) C32 H32A 0.961(3) C33 H33A 0.960(4) C32 H32C 0.960(3) C33 H33C 0.959(3) C33 H33B 0.960(3) C34 H34B 0.961(3) C34 H34A 0.960(3) C38 H38A 0.960(3) C34 H34C 0.959(3) C38 H38C 0.960(3) C38 H38B 0.959(3) H4 O4 0.845 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 116.3(2) C1 C2 C3 121.0(2) C2 C3 C4 122.5(2) C3 C4 C5 116.3(2) C4 C5 C6 121.3(2) C4 C5 C8 144.7(2) C6 C5 C8 94.0(2) C1 C6 C5 122.4(2) C1 C6 C7 143.9(2) C5 C6 C7 93.6(2) C6 C7 C8 86.1(2) C6 C7 C9 117.4(2) C6 C7 O1 113.6(2) C8 C7 C9 117.1(2) C8 C7 O1 114.6(2) C9 C7 O1 107.2(2) C5 C8 C7 86.3(2) C7 C9 C10 109.3(2) C7 C9 C16 109.0(2) C7 C9 C17 107.6(2) C10 C9 C16 108.3(2) C10 C9 C17 113.1(2) C16 C9 C17 109.6(2) C9 C10 C11 118.8(2) C9 C10 O2 108.4(2) C11 C10 O2 106.5(2) C10 C11 C12 115.0(2) C10 C11 C13 109.9(2) C12 C11 C13 109.5(2) C15 C14 O2 111.1(2) C15 C14 O3 124.9(2) O2 C14 O3 124.1(2) C19 C18 C23 122.0(3) C19 C18 C25 144.1(3) C23 C18 C25 93.9(3) C18 C19 C20 115.8(3) C19 C20 C21 122.0(3) C20 C21 C22 122.8(3) C21 C22 C23 115.7(3) C18 C23 C22 121.7(3) C18 C23 C24 93.5(3) C22 C23 C24 144.8(3) C23 C24 C25 86.1(2) C23 C24 C26 116.5(3) C23 C24 O4 113.9(2) C25 C24 C26 117.3(2) C25 C24 O4 114.4(2) C26 C24 O4 107.7(2) C18 C25 C24 86.6(2) C24 C26 C27 109.1(2) C24 C26 C33 109.4(2) C24 C26 C34 106.8(2) C27 C26 C33 109.1(2) C27 C26 C34 112.6(2) C33 C26 C34 109.6(2) C26 C27 C28 118.6(2) C26 C27 O5 108.3(2) C28 C27 O5 106.8(2) C27 C28 C30 115.1(2) C27 C28 C38 109.6(2) C30 C28 C38 109.7(2) C32 C31 O5 110.8(3) C32 C31 O6 125.0(3) O5 C31 O6 124.2(3) C10 O2 C14 118.4(2) C27 O5 C31 119.0(2) C2 C1 H1 122.1(2) C6 C1 H1 121.5(3) C1 C2 H2 119.4(3) C3 C2 H2 119.6(3) C2 C3 H3 118.8(3) C4 C3 H3 118.7(3) C3 C4 H4 122.6(3) C5 C4 H4 121.0(3) C5 C8 H8A 115.1(2) C5 C8 H8B 115.1(2) C7 C8 H8A 115.5(2) C7 C8 H8B 114.7(2) H8A C8 H8B 108.9(3) C9 C10 H10 109.5(2) C11 C10 H10 103.6(2) H10 C10 O2 109.8(2) C10 C11 H11 107.9(3) C12 C11 H11 107.6(2) C13 C11 H11 106.5(2) C11 C12 H12A 115.1(2) C11 C12 H12B 107.5(2) C11 C12 H12C 108.4(2) H12A C12 H12B 108.3(2) H12A C12 H12C 108.4(2) H12B C12 H12C 109.0(2) C11 C13 H13A 109.5(2) C11 C13 H13B 109.1(2) C11 C13 H13C 109.2(2) H13A C13 H13B 109.9(2) H13A C13 H13C 110.0(3) H13B C13 H13C 109.1(2) C14 C15 H15A 111.2(2) C14 C15 H15B 108.6(2) C14 C15 H15C 109.9(2) H15A C15 H15B 109.1(2) H15A C15 H15C 109.1(2) H15B C15 H15C 109.0(2) C9 C16 H16A 108.8(3) C9 C16 H16B 110.1(3) C9 C16 H16C 109.3(2) H16A C16 H16B 109.8(3) H16A C16 H16C 109.9(3) H16B C16 H16C 109.0(3) C9 C17 H17A 108.1(3) C9 C17 H17B 109.8(3) C9 C17 H17C 110.2(3) H17A C17 H17B 109.9(3) H17A C17 H17C 109.7(3) H17B C17 H17C 109.0(3) C18 C19 H19 121.6(3) C20 C19 H19 122.7(2) C19 C20 H20 118.4(3) C21 C20 H20 119.6(3) C20 C21 H21 118.5(3) C22 C21 H21 118.7(3) C21 C22 H22 123.1(3) C23 C22 H22 121.2(3) C18 C25 H25A 115.1(16) C18 C25 H25B 114.9(3) C24 C25 H25A 115.2(16) C24 C25 H25B 114.7(3) H25A C25 H25B 109.0(15) C26 C27 H27 103.1(2) C28 C27 H27 110.3(2) H27 C27 O5 109.5(2) C27 C28 H28 107.7(18) C30 C28 H28 107.7(17) C38 C28 H28 106.7(17) C28 C30 H30A 114.9(2) C28 C30 H30B 107.7(2) C28 C30 H30C 108.4(2) H30A C30 H30B 108.3(2) H30A C30 H30C 108.5(2) H30B C30 H30C 109.0(3) C31 C32 H32A 110.9(3) C31 C32 H32B 108.9(3) C31 C32 H32C 109.5(3) H32A C32 H32B 109.3(3) H32A C32 H32C 109.3(3) H32B C32 H32C 109.0(3) C26 C33 H33A 109.1(3) C26 C33 H33B 110.2(3) C26 C33 H33C 109.1(3) H33A C33 H33B 109.7(3) H33A C33 H33C 109.6(3) H33B C33 H33C 109.1(3) C26 C34 H34A 113.4(3) C26 C34 H34B 108.3(3) C26 C34 H34C 109.0(2) H34A C34 H34B 108.5(3) H34A C34 H34C 108.5(3) H34B C34 H34C 109.1(3) C28 C38 H38A 109.2(3) C28 C38 H38B 109.8(3) C28 C38 H38C 108.9(3) H38A C38 H38B 109.9(3) H38A C38 H38C 109.9(3) H38B C38 H38C 109.1(3) C24 O4 H4 101.6(2)