Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email HIEMSTRA@SCIENCE.UVA.NL _publ_contact_author_name 'Prof Henk Hiemstra' _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name H.Hiemstra K.Coubitz J.Dijkink J.Fraanje F.S.Guziec B.T.B.Hue ; S.Kuiper ; K.K.Larson H.Schenk 'J.H.van Maarseveen' data_Compound_12 _database_code_depnum_ccdc_archive 'CCDC 222276' _chemical_formula_sum 'C12 H14 O2' _chemical_formula_moiety ? _chemical_formula_weight 190.24 _chemical_melting_point ? _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 6.6969(4) _cell_length_b 7.0489(6) _cell_length_c 10.9328(7) _cell_angle_alpha 77.964(6) _cell_angle_beta 75.679(9) _cell_angle_gamma 80.977(8) _cell_volume 486.04(6) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.3 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 40.43 _cell_measurement_theta_max 42.88 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu .698 _exptl_crystal_description ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_colour ? _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number ? _reflns_number_total 1999 _reflns_Friedel_coverage ? _reflns_number_gt 1806 _reflns_threshold_expression 'Iobs > 2.50 sig(Iobs)' _diffrn_reflns_theta_max 74.73 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 #<< do not append units _diffrn_standards_decay_% 13 #<< do not append % _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .079 _refine_ls_wR_factor_ref .099 _refine_ls_goodness_of_fit_ref .996 _refine_ls_number_reflns 1806 _refine_ls_number_parameters 184 _refine_ls_weighting_scheme calc _refine_ls_weighting_details '1/[0.6 + 0.01*(\s(Fobs)^2^) + 0.01/(\s(Fobs))]' _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max .135 _refine_diff_density_min -.345 _refine_diff_density_max .352 _refine_ls_extinction_method Zachariasen _refine_ls_extinction_coef 1470(151) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Enraf-Nonius CAD4 software' _computing_cell_refinement 'local program' _computing_data_reduction 'xtal ADDREF' _computing_structure_solution CRUNCH _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics PLATON _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 24 .017 .009 'Int Tables Vol IV Tables 2.2B and 2.3.1' H ? 0 28 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' O ? 0 4 .047 .032 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 .3111(6) .3090(5) .7186(3) .028(3) Uani ? ? 1.00000 ? ? C2 .3550(7) .2853(6) .5795(4) .039(3) Uani ? ? 1.00000 ? ? C3 .2178(8) .1409(7) .5643(4) .049(4) Uani ? ? 1.00000 ? ? C4 -.0097(8) .1935(8) .6214(5) .054(4) Uani ? ? 1.00000 ? ? C5 -.0494(7) .1891(7) .7667(5) .046(4) Uani ? ? 1.00000 ? ? C6 .0801(6) .3269(5) .7916(4) .032(3) Uani ? ? 1.00000 ? ? C7 .1815(7) .2677(6) .9136(4) .039(3) Uani ? ? 1.00000 ? ? C8 .2992(7) .4430(7) .9028(4) .043(4) Uani ? ? 1.00000 ? ? C9 .3485(6) .4981(6) .7567(4) .036(3) Uani ? ? 1.00000 ? ? O1 .1761(5) .6401(4) .7245(3) .045(2) Uani ? ? 1.00000 ? ? C10 .0076(7) .5411(6) .7582(4) .040(3) Uani ? ? 1.00000 ? ? O2 -.1640(5) .6200(5) .7557(4) .063(3) Uani ? ? 1.00000 ? ? C11 .3451(6) .1502(6) .8284(4) .034(3) Uani ? ? 1.00000 ? ? C12 .4497(8) -.0279(7) .8421(5) .053(4) Uani ? ? 1.00000 ? ? H21 .298(10) .412(5) .532(6) .11(2) Uiso ? ? 1.00000 ? ? H22 .508(2) .244(7) .558(5) .056(14) Uiso ? ? 1.00000 ? ? H31 .246(7) .153(7) .4690(11) .057(14) Uiso ? ? 1.00000 ? ? H32 .262(11) .009(5) .611(6) .13(3) Uiso ? ? 1.00000 ? ? H41 -.044(8) .334(3) .586(5) .070(17) Uiso ? ? 1.00000 ? ? H42 -.080(8) .078(5) .623(5) .070(16) Uiso ? ? 1.00000 ? ? H51 -.203(2) .203(7) .799(5) .058(15) Uiso ? ? 1.00000 ? ? H52 -.033(9) .059(4) .822(5) .09(2) Uiso ? ? 1.00000 ? ? H7 .084(6) .205(6) .991(3) .050(13) Uiso ? ? 1.00000 ? ? H81 .199(7) .559(6) .923(6) .09(2) Uiso ? ? 1.00000 ? ? H82 .421(5) .414(7) .945(4) .052(13) Uiso ? ? 1.00000 ? ? H9 .473(4) .567(5) .710(3) .026(10) Uiso ? ? 1.00000 ? ? H121 .474(8) -.118(6) .923(3) .073(17) Uiso ? ? 1.00000 ? ? H122 .519(13) -.064(14) .756(4) .18(4) Uiso ? ? 1.00000 ? ? 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 .0308(18) .0296(18) .0272(18) -.0035(14) -.0048(14) -.0120(14) C2 .047(2) .041(2) .028(2) -.0050(19) -.0010(17) -.0152(17) C3 .072(3) .045(3) .037(2) -.008(2) -.013(2) -.022(2) C4 .063(3) .054(3) .058(3) -.018(2) -.029(3) -.014(2) C5 .038(2) .047(3) .055(3) -.014(2) -.006(2) -.011(2) C6 .032(2) .031(2) .032(2) -.0013(15) -.0021(15) -.0098(16) C7 .050(2) .040(2) .026(2) -.0021(19) -.0047(17) -.0085(17) C8 .056(3) .044(2) .040(2) .005(2) -.021(2) -.023(2) C9 .040(2) .033(2) .042(2) -.0045(16) -.0129(18) -.0136(17) O1 .059(2) .0271(15) .0525(18) .0007(13) -.0160(15) -.0125(13) C10 .042(2) .039(2) .039(2) .0067(18) -.0093(18) -.0164(18) O2 .054(2) .064(2) .074(2) .0241(17) -.0246(18) -.0267(19) C11 .038(2) .034(2) .036(2) .0034(16) -.0159(17) -.0124(16) C12 .063(3) .037(2) .063(3) .013(2) -.029(3) -.016(2) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter y(es) for value to be published C1 C11 . . 1.497(5) ? C1 C2 . . 1.515(6) ? C1 C9 . . 1.550(6) ? C1 C6 . . 1.555(5) ? C2 H22 . . 1.002(17) ? C2 H21 . . 1.00(5) ? C2 C3 . . 1.532(8) ? C3 H31 . . 1.000(14) ? C3 H32 . . 1.00(4) ? C3 C4 . . 1.516(7) ? C4 H41 . . 1.00(2) ? C4 H42 . . 1.00(5) ? C4 C5 . . 1.538(8) ? C5 H51 . . .997(14) ? C5 H52 . . 1.00(3) ? C5 C6 . . 1.503(7) ? C6 C10 . . 1.509(5) ? C6 C7 . . 1.594(6) ? C7 H7 . . 1.00(3) ? C7 C11 . . 1.512(5) ? C7 C8 . . 1.537(7) ? C8 H81 . . 1.00(4) ? C8 H82 . . 1.00(4) ? C8 C9 . . 1.527(6) ? C9 H9 . . 1.00(3) ? C9 O1 . . 1.467(5) ? O1 C10 . . 1.353(6) ? C10 O2 . . 1.200(6) ? C11 C12 . . 1.337(6) ? C12 H122 . . 1.00(6) ? C12 H121 . . 1.00(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter yes for value to be published C11 C1 C2 . . . 125.4(3) ? C11 C1 C9 . . . 104.9(3) ? C11 C1 C6 . . . 85.8(3) ? C2 C1 C9 . . . 121.6(3) ? C2 C1 C6 . . . 117.0(4) ? C9 C1 C6 . . . 92.0(3) ? H22 C2 H21 . . . 119(4) ? H22 C2 C1 . . . 104(3) ? H22 C2 C3 . . . 115(3) ? H21 C2 C1 . . . 106(3) ? H21 C2 C3 . . . 102(4) ? C1 C2 C3 . . . 110.0(3) ? H31 C3 H32 . . . 115(5) ? H31 C3 C4 . . . 112(3) ? H31 C3 C2 . . . 102(3) ? H32 C3 C4 . . . 108(4) ? H32 C3 C2 . . . 108(5) ? C4 C3 C2 . . . 112.4(4) ? H41 C4 H42 . . . 130(4) ? H41 C4 C3 . . . 107(3) ? H41 C4 C5 . . . 104(3) ? H42 C4 C3 . . . 106(3) ? H42 C4 C5 . . . 99(3) ? C3 C4 C5 . . . 111.5(5) ? H51 C5 H52 . . . 93(4) ? H51 C5 C6 . . . 121(3) ? H51 C5 C4 . . . 106(3) ? H52 C5 C6 . . . 111(4) ? H52 C5 C4 . . . 117(3) ? C6 C5 C4 . . . 109.4(4) ? C5 C6 C10 . . . 115.6(4) ? C5 C6 C1 . . . 114.9(3) ? C5 C6 C7 . . . 119.3(3) ? C10 C6 C1 . . . 103.8(3) ? C10 C6 C7 . . . 115.2(4) ? C1 C6 C7 . . . 82.2(3) ? H7 C7 C11 . . . 122(2) ? H7 C7 C8 . . . 127(3) ? H7 C7 C6 . . . 112(2) ? C11 C7 C8 . . . 99.3(3) ? C11 C7 C6 . . . 83.9(3) ? C8 C7 C6 . . . 102.7(3) ? H81 C8 H82 . . . 117(5) ? H81 C8 C9 . . . 99(3) ? H81 C8 C7 . . . 110(3) ? H82 C8 C9 . . . 117(2) ? H82 C8 C7 . . . 115(3) ? C9 C8 C7 . . . 97.3(4) ? H9 C9 O1 . . . 102.8(17) ? H9 C9 C8 . . . 121(2) ? H9 C9 C1 . . . 121(2) ? O1 C9 C8 . . . 106.0(3) ? O1 C9 C1 . . . 103.9(4) ? C8 C9 C1 . . . 101.1(3) ? C10 O1 C9 . . . 105.9(3) ? O2 C10 O1 . . . 122.6(4) ? O2 C10 C6 . . . 129.4(4) ? O1 C10 C6 . . . 107.9(3) ? C12 C11 C1 . . . 136.2(4) ? C12 C11 C7 . . . 136.2(4) ? C1 C11 C7 . . . 87.0(3) ? H122 C12 H121 . . . 120(5) ? H122 C12 C11 . . . 111(5) ? H121 C12 C11 . . . 129(2) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter yes for value to be published C6 C1 C2 C3 . . . . -42.7(5) ? C6 C1 C2 H21 . . . . 67(4) ? C6 C1 C2 H22 . . . . -167(3) ? C9 C1 C2 C3 . . . . -153.7(4) ? C9 C1 C2 H21 . . . . -44(4) ? C9 C1 C2 H22 . . . . 82(3) ? C11 C1 C2 C3 . . . . 62.5(5) ? C11 C1 C2 H21 . . . . 172(4) ? C11 C1 C2 H22 . . . . -61(3) ? C2 C1 C6 C5 . . . . 42.4(5) ? C2 C1 C6 C7 . . . . 161.1(3) ? C2 C1 C6 C10 . . . . -84.8(4) ? C9 C1 C6 C5 . . . . 169.7(3) ? C9 C1 C6 C7 . . . . -71.6(3) ? C9 C1 C6 C10 . . . . 42.5(4) ? C11 C1 C6 C5 . . . . -85.5(4) ? C11 C1 C6 C7 . . . . 33.2(3) ? C11 C1 C6 C10 . . . . 147.3(4) ? C2 C1 C9 C8 . . . . -175.7(4) ? C2 C1 C9 O1 . . . . 74.6(4) ? C2 C1 C9 H9 . . . . -40(2) ? C6 C1 C9 C8 . . . . 60.7(3) ? C6 C1 C9 O1 . . . . -49.1(3) ? C6 C1 C9 H9 . . . . -163(2) ? C11 C1 C9 C8 . . . . -25.5(4) ? C11 C1 C9 O1 . . . . -135.2(3) ? C11 C1 C9 H9 . . . . 110(2) ? C2 C1 C11 C7 . . . . -155.4(4) ? C2 C1 C11 C12 . . . . 16.0(8) ? C6 C1 C11 C7 . . . . -34.9(3) ? C6 C1 C11 C12 . . . . 136.4(6) ? C9 C1 C11 C7 . . . . 56.0(3) ? C9 C1 C11 C12 . . . . -132.7(6) ? C1 C2 C3 C4 . . . . 52.3(5) ? C1 C2 C3 H31 . . . . 172(3) ? C1 C2 C3 H32 . . . . -66(4) ? H21 C2 C3 C4 . . . . -60(3) ? H21 C2 C3 H31 . . . . 60(4) ? H21 C2 C3 H32 . . . . -179(5) ? H22 C2 C3 C4 . . . . 169(3) ? H22 C2 C3 H31 . . . . -71(4) ? H22 C2 C3 H32 . . . . 50(5) ? C2 C3 C4 C5 . . . . -61.8(5) ? C2 C3 C4 H41 . . . . 51(3) ? C2 C3 C4 H42 . . . . -168(3) ? H31 C3 C4 C5 . . . . -176(3) ? H31 C3 C4 H41 . . . . -63(5) ? H31 C3 C4 H42 . . . . 78(5) ? H32 C3 C4 C5 . . . . 57(5) ? H32 C3 C4 H41 . . . . 169(6) ? H32 C3 C4 H42 . . . . -50(6) ? C3 C4 C5 C6 . . . . 57.5(5) ? C3 C4 C5 H51 . . . . -171(3) ? C3 C4 C5 H52 . . . . -69(4) ? H41 C4 C5 C6 . . . . -57(3) ? H41 C4 C5 H51 . . . . 75(5) ? H41 C4 C5 H52 . . . . 176(5) ? H42 C4 C5 C6 . . . . 168(3) ? H42 C4 C5 H51 . . . . -60(4) ? H42 C4 C5 H52 . . . . 42(5) ? C4 C5 C6 C1 . . . . -47.2(5) ? C4 C5 C6 C7 . . . . -142.4(4) ? C4 C5 C6 C10 . . . . 73.7(4) ? H51 C5 C6 C1 . . . . -171(3) ? H51 C5 C6 C7 . . . . 94(3) ? H51 C5 C6 C10 . . . . -50(3) ? H52 C5 C6 C1 . . . . 83(3) ? H52 C5 C6 C7 . . . . -12(3) ? H52 C5 C6 C10 . . . . -156(3) ? C1 C6 C7 C8 . . . . 65.2(3) ? C1 C6 C7 C11 . . . . -32.9(3) ? C1 C6 C7 H7 . . . . -155(3) ? C5 C6 C7 C8 . . . . 179.5(3) ? C5 C6 C7 C11 . . . . 81.3(4) ? C5 C6 C7 H7 . . . . -41(3) ? C10 C6 C7 C8 . . . . -36.4(4) ? C10 C6 C7 C11 . . . . -134.6(3) ? C10 C6 C7 H7 . . . . 103(3) ? C1 C6 C10 O1 . . . . -23.4(5) ? C1 C6 C10 O2 . . . . 154.3(5) ? C5 C6 C10 O1 . . . . -150.2(4) ? C5 C6 C10 O2 . . . . 27.6(7) ? C7 C6 C10 O1 . . . . 64.4(4) ? C7 C6 C10 O2 . . . . -117.9(6) ? C6 C7 C8 C9 . . . . -30.6(4) ? C6 C7 C8 H81 . . . . 72(4) ? C6 C7 C8 H82 . . . . -154(3) ? C11 C7 C8 C9 . . . . 55.2(4) ? C11 C7 C8 H81 . . . . 157(4) ? C11 C7 C8 H82 . . . . -69(3) ? H7 C7 C8 C9 . . . . -161(3) ? H7 C7 C8 H81 . . . . -59(5) ? H7 C7 C8 H82 . . . . 75(4) ? C6 C7 C11 C1 . . . . 34.1(3) ? C6 C7 C11 C12 . . . . -137.3(7) ? C8 C7 C11 C1 . . . . -67.8(4) ? C8 C7 C11 C12 . . . . 120.8(7) ? H7 C7 C11 C1 . . . . 146(3) ? H7 C7 C11 C12 . . . . -25(3) ? C7 C8 C9 C1 . . . . -17.0(4) ? C7 C8 C9 O1 . . . . 91.1(4) ? C7 C8 C9 H9 . . . . -153(2) ? H81 C8 C9 C1 . . . . -129(3) ? H81 C8 C9 O1 . . . . -20(3) ? H81 C8 C9 H9 . . . . 95(4) ? H82 C8 C9 C1 . . . . 106(3) ? H82 C8 C9 O1 . . . . -146(3) ? H82 C8 C9 H9 . . . . -30(4) ? C1 C9 O1 C10 . . . . 39.4(4) ? C8 C9 O1 C10 . . . . -66.7(5) ? H9 C9 O1 C10 . . . . 166(2) ? C9 O1 C10 C6 . . . . -9.5(5) ? C9 O1 C10 O2 . . . . 172.6(5) ? C1 C11 C12 H121 . . . . 173(4) ? C1 C11 C12 H122 . . . . -2(6) ? C7 C11 C12 H121 . . . . -20(4) ? C7 C11 C12 H122 . . . . 165(6) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter yes for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- 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 H51 H52 1.44(6) . . ? H31 H32 1.69(7) . . ? H81 H82 1.70(6) . . ? H21 H22 1.73(6) . . ? H121 H122 1.74(6) . . ? H41 H42 1.81(4) . . ? C11 H122 1.94(8) . . ? O1 H9 1.95(2) . . ? C9 H81 1.95(6) . . ? C5 H42 1.96(6) . . ? C2 H31 1.99(5) . . ? C3 H21 2.00(4) . . ? C1 H22 2.01(4) . . ? C5 H41 2.02(5) . . ? C3 H42 2.03(5) . . ? C1 H21 2.04(6) . . ? C3 H41 2.04(4) . . ? C4 H51 2.05(4) . . ? C4 H32 2.06(6) . . ? C1 C7 2.070(5) . . ? C2 H32 2.07(5) . . ? C6 C11 2.077(5) . . ? C6 H52 2.08(4) . . ? C7 H81 2.10(4) . . ? C4 H31 2.10(3) . . ? C11 H121 2.12(4) . . ? C3 H22 2.16(3) . . ? C7 H82 2.16(4) . . ? O1 H81 2.17(6) . . ? C9 H82 2.17(4) . . ? C6 H7 2.17(3) . . ? C4 H52 2.18(5) . . ? H21 H31 2.18(7) . . ? C6 H51 2.19(3) . . ? H42 H51 2.20(7) . . ? C8 H9 2.21(3) . . ? C11 H7 2.21(3) . . ? C1 H9 2.23(4) . . ? C6 C9 2.232(6) . . ? H32 H42 2.24(9) . . ? O1 O2 2.241(5) . . ? H42 H52 2.25(8) . . ? C9 C10 2.252(6) . . ? C8 H7 2.28(4) . . ? C7 C9 2.299(5) . . ? C6 O1 2.316(5) . . ? C8 C11 2.323(7) . . ? H21 H41 2.34(8) . . ? H41 H51 2.36(6) . . ? C1 O1 2.375(4) . . ? C1 C8 2.376(7) . . ? H31 H41 2.39(6) . . ? C8 O1 2.391(5) . . ? H82 H82 2.39(7) . '2 667' ? H82 H121 2.39(6) . '2 657' ? H22 H32 2.40(7) . . ? C1 C10 2.411(5) . . ? C9 C11 2.416(5) . . ? H22 H31 2.43(6) . . ? C6 C8 2.445(7) . . ? C6 O2 2.452(5) . . ? H7 H81 2.45(6) . '2 567' ? H52 H7 2.46(5) . '2 557' ? H31 H42 2.46(6) . . ? C4 C6 2.483(8) . . ? C10 H81 2.49(7) . . ? C1 C3 2.495(7) . . ? C3 C5 2.525(6) . . ? H82 H9 2.53(5) . . ? C2 C4 2.532(8) . . ? C5 C10 2.548(7) . . ? H32 H122 2.55(11) . . ? C6 H41 2.57(6) . . ? C1 C5 2.578(6) . . ? H81 H9 2.58(6) . . ? H31 H42 2.59(7) . '2 556' ? H52 H7 2.61(7) . . ? C2 C6 2.618(5) . . ? C7 C10 2.620(6) . . ? C2 H41 2.62(6) . . ? H7 H81 2.62(6) . . ? C1 C12 2.630(6) . . ? C11 H82 2.63(5) . . ? H21 H41 2.63(7) . '2 566' ? C4 H21 2.64(6) . . ? C7 C12 2.644(6) . . ? C5 C7 2.673(8) . . ? C2 C9 2.675(7) . . ? C5 H32 2.68(6) . . ? C2 C11 2.677(6) . . ? H32 H52 2.68(8) . . ? C7 H52 2.69(6) . . ? O2 H9 2.70(3) . '1 455' ? H21 H9 2.70(6) . '2 666' ? C6 H81 2.71(6) . . ? H31 H122 2.71(6) . '2 656' ? H121 H121 2.71(7) . '2 657' ? H41 H41 2.72(4) . '2 566' ? C1 H32 2.72(6) . . ? O1 H32 2.72(4) . '1 565' ? C11 H52 2.73(6) . . ? C10 H41 2.73(5) . . ? C8 C10 2.727(7) . . ? H22 H122 2.74(8) . . ? C9 H21 2.76(7) . . ? O2 H31 2.77(3) . '2 566' ? H7 H82 2.77(6) . . ? C1 H122 2.78(9) . . ? O1 H21 2.80(6) . . ? H21 H22 2.81(6) . '2 666' ? H21 H32 2.82(5) . . ? O2 H122 2.82(9) . '1 465' ? H9 H122 2.83(11) . '1 565' ? C5 H7 2.83(4) . . ? H32 H41 2.84(7) . . ? C6 H21 2.84(6) . . ? C5 C11 2.844(7) . . ? H22 H32 2.85(7) . '2 656' ? C10 H51 2.86(5) . . ? C11 H22 2.86(4) . . ? C3 H52 2.89(5) . . ? H41 H52 2.90(6) . . ? C1 C4 2.906(8) . . ? H81 H81 2.91(6) . '2 567' ? O2 H41 2.91(4) . . ? O2 H51 2.92(5) . . ? C3 C6 2.931(6) . . ? C12 H51 2.93(4) . '1 655' ? H42 H122 2.94(10) . '1 455' ? H22 H9 2.94(6) . '2 666' ? C10 H21 2.96(6) . . ? C11 H32 2.96(8) . . ? H21 H9 2.96(8) . . ? C2 H9 2.97(4) . . ? C7 H81 2.97(5) . '2 567' ? C1 H52 2.97(5) . . ? C1 H7 2.98(3) . . ? C7 O1 2.985(5) . . ? C9 H22 2.99(5) . . ? H51 H82 2.99(5) . '1 455' ? C5 O2 2.998(6) . . ? H31 H9 3.00(5) . '2 666' ? C1 H82 3.01(5) . . ? H42 H42 3.01(8) . '2 556' ? C1 H81 3.01(6) . . ? H21 H21 3.02(9) . '2 666' ? H51 H122 3.02(11) . '1 455' ? H22 H42 3.02(6) . '1 655' ? H22 H9 3.03(7) . . ? C12 H7 3.04(3) . . ? C11 H51 3.04(2) . '1 655' ? C12 H32 3.04(8) . . ? C2 C5 3.039(6) . . ? C2 H122 3.04(7) . . ? C1 H41 3.04(6) . . ? H22 H31 3.05(6) . '2 656' ? C10 H9 3.06(3) . . ? C7 H121 3.09(5) . . ? C2 H9 3.11(3) . '2 666' ? C11 H9 3.11(3) . . ? C8 H121 3.12(4) . '2 657' ? H51 H121 3.13(5) . '2 557' ? C12 H121 3.14(5) . '2 657' ? H81 H121 3.15(8) . '1 565' ? C4 C10 3.156(8) . . ? C2 O1 3.159(5) . . ? C10 H7 3.17(3) . . ? H51 H7 3.18(6) . . ? C3 H42 3.18(6) . '2 556' ? C7 H121 3.18(5) . '2 657' ? C8 H82 3.19(5) . '2 667' ? C6 H9 3.19(3) . . ? C11 H81 3.19(5) . . ? C6 H32 3.19(6) . . ? C11 H121 3.19(5) . '2 657' ? H7 H7 3.22(6) . '2 557' ? C7 H9 3.22(3) . . ? C3 C11 3.222(7) . . ? C2 C10 3.223(6) . . ? H7 H121 3.23(6) . . ? H51 H121 3.23(6) . '1 455' ? O2 H121 3.23(4) . '1 465' ? H51 H9 3.24(5) . '1 455' ? C3 H122 3.24(7) . . ? C2 H21 3.24(6) . '2 666' ? C12 H52 3.24(6) . . ? C6 H42 3.25(6) . . ? O1 H82 3.25(4) . . ? C12 H22 3.26(4) . . ? H7 H121 3.26(7) . '2 657' ? C7 H51 3.26(4) . . ? H22 H41 3.26(6) . '1 655' ? C9 H7 3.26(3) . . ? H81 H82 3.27(7) . '2 667' ? H31 H32 3.28(8) . '2 656' ? O2 H82 3.28(4) . '2 567' ? C1 H31 3.29(4) . . ? C6 C12 3.294(6) . . ? H32 H42 3.29(10) . '2 556' ? H32 H9 3.30(5) . '1 545' ? O1 H22 3.31(4) . '2 666' ? C5 H21 3.31(5) . . ? O2 H81 3.31(6) . . ? O2 H42 3.32(4) . '1 565' ? O1 H52 3.33(4) . '1 565' ? H82 H121 3.33(7) . '1 565' ? C6 H82 3.34(5) . . ? C7 H52 3.34(4) . '2 557' ? C12 H82 3.34(4) . '2 657' ? C2 H42 3.35(5) . . ? C3 H51 3.35(3) . . ? C3 H22 3.36(4) . '2 656' ? O2 H82 3.36(3) . '1 455' ? C10 C11 3.363(5) . . ? C10 H52 3.37(3) . . ? C2 C12 3.368(7) . . ? C10 H81 3.38(6) . '2 567' ? O2 C12 3.391(6) . '1 465' ? O1 H42 3.40(4) . '1 565' ? C6 H22 3.40(3) . . ? C6 H81 3.40(6) . '2 567' ? C5 H31 3.40(2) . . ? C8 H81 3.40(5) . '2 567' ? C9 O2 3.407(6) . . ? C7 H122 3.41(8) . . ? C5 H7 3.41(3) . '2 557' ? H51 H7 3.41(6) . '2 557' ? C4 H22 3.42(3) . '1 455' ? C4 H22 3.423(19) . . ? C12 H9 3.43(4) . '1 545' ? O2 H81 3.43(6) . '2 567' ? C8 H7 3.44(4) . '2 567' ? C11 H21 3.44(6) . . ? C12 H81 3.44(4) . '1 545' ? O2 H7 3.44(4) . '2 567' ? C9 H51 3.45(3) . '1 655' ? C9 H21 3.45(6) . '2 666' ? C9 H122 3.45(10) . '1 565' ? O1 H122 3.46(10) . '1 565' ? C10 H7 3.46(4) . '2 567' ? C8 C12 3.466(7) . . ? O1 H7 3.47(3) . '2 567' ? H41 H9 3.48(5) . '1 455' ? C4 H42 3.49(5) . '2 556' ? C12 H82 3.49(5) . . ? C1 H51 3.50(2) . . ? H32 H32 3.50(9) . '2 656' ? C9 O2 3.501(6) . '1 655' ? C4 H21 3.50(5) . '2 566' ? O1 C11 3.503(5) . . ? C1 H51 3.50(3) . '1 655' ? C2 H22 3.51(4) . '2 666' ? C4 O2 3.518(7) . . ? C9 H22 3.52(4) . '2 666' ? H52 H122 3.52(12) . '1 455' ? C10 H31 3.52(4) . '2 566' ? C8 H51 3.53(3) . '1 655' ? H32 H51 3.53(7) . . ? C2 H52 3.53(5) . . ? C2 C7 3.530(6) . . ? C4 H31 3.53(5) . '2 556' ? C12 H42 3.53(5) . '1 655' ? O2 H21 3.54(7) . '2 566' ? H9 H121 3.54(6) . '1 565' ? C8 H121 3.54(5) . '1 565' ? C1 H121 3.55(4) . . ? H21 H42 3.55(7) . . ? O1 H41 3.55(5) . . ? H52 H121 3.55(8) . '1 455' ? C1 O2 3.555(5) . . ? C12 H52 3.56(6) . '1 655' ? H22 H22 3.56(6) . '2 666' ? H52 H121 3.56(6) . '2 557' ? C8 O2 3.566(6) . '2 567' ? C2 H32 3.57(6) . '2 656' ? H22 H51 3.57(6) . '1 655' ? H81 H122 3.58(10) . '1 565' ? H52 H122 3.59(10) . . ? C7 O2 3.589(6) . . ? C2 H41 3.59(4) . '2 566' ? H22 H41 3.60(6) . . ? O2 H52 3.60(5) . '1 565' ? C4 C11 3.606(8) . . ? O2 H41 3.61(5) . '2 566' ? C3 O1 3.618(5) . '1 545' ? C3 H122 3.62(5) . '2 656' ? C5 O1 3.626(6) . . ? C9 C12 3.628(6) . . ? C4 H41 3.63(3) . '2 566' ? C3 O2 3.632(6) . '2 566' ? C10 H41 3.64(5) . '2 566' ? H31 H41 3.64(5) . '2 566' ? C3 H9 3.64(3) . '2 666' ? C9 H32 3.64(4) . '1 565' ? C3 C12 3.647(8) . . ? C3 H32 3.65(7) . '2 656' ? C5 H122 3.66(10) . '1 455' ? C5 C12 3.665(7) . . ? C5 C9 3.665(7) . . ? O1 H41 3.67(6) . '2 566' ? C6 H122 3.71(8) . . ? C12 H31 3.71(3) . '2 656' ? C4 H122 3.71(9) . '1 455' ? C10 H9 3.72(3) . '1 455' ? C11 H51 3.72(2) . . ? C10 H82 3.72(4) . . ? C2 C2 3.733(6) . '2 666' ? C5 C12 3.740(8) . '1 455' ? C1 H42 3.74(6) . . ? O2 H21 3.75(5) . . ? C1 H21 3.75(5) . '2 666' ? C8 O2 3.766(6) . . ? O1 H22 3.77(4) . . ? C3 C10 3.769(7) . . ? O1 H7 3.77(3) . . ? C10 H42 3.77(3) . '1 565' ? O1 C12 3.775(7) . '1 565' ? C8 C10 3.781(6) . '2 567' ? C12 C12 3.784(9) . '2 657' ? C2 H31 3.79(5) . '2 656' ? C10 H82 3.79(4) . '2 567' ? C10 H52 3.81(4) . '1 565' ? C10 H32 3.82(5) . '1 565' ? C6 H31 3.82(3) . . ? C3 H31 3.83(5) . '2 656' ? C7 O2 3.830(6) . '2 567' ? C2 C8 3.837(7) . . ? C8 O2 3.844(6) . '1 655' ? C2 C9 3.845(5) . '2 666' ? C5 H121 3.85(4) . '2 557' ? C9 C12 3.850(7) . '1 565' ? C3 H41 3.85(3) . '2 566' ? C9 H121 3.85(5) . '1 565' ? C7 H7 3.85(4) . '2 557' ? C12 H7 3.86(4) . '2 557' ? C8 H122 3.86(9) . '1 565' ? O1 H31 3.87(4) . '2 566' ? O2 H52 3.87(3) . . ? C7 C8 3.873(6) . '2 567' ? C5 H82 3.87(3) . '1 455' ? C5 C8 3.874(8) . . ? C4 C7 3.879(8) . . ? C12 H82 3.88(5) . '1 545' ? C12 H51 3.88(4) . '2 557' ? C5 H22 3.89(2) . . ? C8 C12 3.896(7) . '1 565' ? C12 H7 3.91(4) . '2 657' ? C5 H9 3.91(3) . '1 455' ? C3 C9 3.917(8) . . ? C8 H121 3.92(4) . . ? O2 H7 3.92(3) . . ? C4 O1 3.920(6) . '1 545' ? C5 H122 3.93(8) . . ? C7 C10 3.941(6) . '2 567' ? O1 H21 3.94(6) . '2 666' ? C2 H42 3.95(5) . '1 655' ? C10 H122 3.95(8) . '1 465' ? C9 H122 3.95(9) . . ? C2 H51 3.96(2) . . ? C11 H42 3.96(5) . '1 655' ? C5 H121 3.96(5) . '1 455' ? C9 H31 3.97(4) . '2 666' ? C4 H32 3.97(8) . '2 556' ? C11 H52 3.98(5) . '2 557' ? C2 O1 3.976(5) . '2 666' ? C11 H7 3.98(4) . '2 557' ? C7 H22 3.98(4) . . ? C7 H51 3.983(13) . '1 655' ? C7 H32 3.98(7) . . ? C5 C11 3.987(6) . '1 455' ? C7 H21 3.99(6) . . ? C5 H81 3.99(6) . '2 567' ? C4 O2 3.991(6) . '2 566' ? C1 H22 4.00(4) . '2 666' ? C9 H41 4.00(6) . . ? C5 O1 4.004(6) . '1 545' ? C3 C4 4.006(9) . '2 556' ? C12 H52 4.01(5) . '2 557' ? C4 O1 4.017(7) . . ? C7 C12 4.020(7) . '2 657' ? C6 H121 4.03(5) . . ? C10 H42 4.03(5) . . ? C3 C7 4.041(7) . . ? C11 C12 4.048(8) . '2 657' ? C3 C3 4.048(7) . '2 656' ? C8 C12 4.066(7) . '2 657' ? C2 O2 4.067(6) . '2 566' ? C8 C8 4.076(8) . '2 667' ? C8 C8 4.088(6) . '2 567' ? C2 C3 4.090(6) . '2 656' ? C4 O1 4.092(7) . '2 566' ? C6 C8 4.125(6) . '2 567' ? C4 C12 4.152(7) . '1 455' ? C4 C4 4.153(9) . '2 556' ? C4 C9 4.153(8) . . ? C2 O2 4.167(5) . . ? C4 C10 4.180(7) . '2 566' ? C3 O1 4.189(6) . . ? C4 O2 4.201(7) . '1 545' ? C7 O1 4.208(5) . '2 567' ? C5 O2 4.232(7) . '1 545' ? C7 C7 4.245(6) . '2 567' ? C3 C10 4.245(7) . '2 566' ? C5 C7 4.248(6) . '2 557' ? C1 C2 4.280(5) . '2 666' ? C4 C12 4.280(8) . . ? C5 C9 4.287(6) . '1 455' ? C2 C4 4.325(8) . '1 655' ? O1 C11 4.372(6) . '1 565' ? C1 C5 4.373(6) . '1 655' ? C4 C11 4.379(6) . '1 455' ? C1 C4 4.392(6) . '1 655' ? C3 C3 4.410(9) . '2 556' ? _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 204 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min -7 _reflns_limit_h_max 8 _reflns_limit_k_min -8 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _reflns_number_observed ? _reflns_d_resolution_high .799 _reflns_d_resolution_low 10.425 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_theta_min 4.24 _diffrn_reflns_reduction_process 'perpendicular monochr Lp' _diffrn_ambient_temperature 293 _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_radiation_detector ? _refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970' _refine_ls_matrix_type full _refine_ls_number_restraints 14 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .085 _refine_ls_wR_factor_all .104 _refine_ls_goodness_of_fit_all .989 _refine_ls_shift/su_mean .01 data_Compound_17 _database_code_depnum_ccdc_archive 'CCDC 222277' _chemical_formula_sum 'C11 H16 O2' _chemical_formula_moiety ? _chemical_formula_weight 180.27 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P_1_21/n_1 _symmetry_space_group_name_Hall -p_2yn loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 7.0166(3) _cell_length_b 10.5703(6) _cell_length_c 13.7222(13) _cell_angle_alpha 90.000 _cell_angle_beta 102.880(5) _cell_angle_gamma 90.000 _cell_volume 992.13(12) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 38.91 _cell_measurement_theta_max 45.08 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu .648 _exptl_crystal_description plate _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_colour ? _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 2030 _reflns_number_total 2030 _reflns_Friedel_coverage ? _reflns_number_gt 1743 _reflns_threshold_expression 'Iobs > 2.50 sig(Iobs)' _diffrn_reflns_theta_max 74.86 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 #<< do not append units _diffrn_standards_decay_% 8 #<< do not append % _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .071 _refine_ls_wR_factor_ref .064 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_number_reflns 1743 _refine_ls_number_parameters 183 _refine_ls_weighting_scheme calc _refine_ls_weighting_details '1/[0.4 + 0.1(\s(Fobs))^2^ + 0.1/(\s(Fobs))]' _refine_ls_hydrogen_treatment riding _refine_ls_shift/su_max .038 _refine_diff_density_min -.293 _refine_diff_density_max .321 _refine_ls_extinction_method Zachariasen _refine_ls_extinction_coef 1931(183) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'Enraf-Nonius CAD-4 software' _computing_cell_refinement 'local program' _computing_data_reduction 'xtal ADDREF' _computing_structure_solution CRUNCH _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics PLATON _computing_publication_material 'xtal BONDLA CIFIO PLATON' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 44 .017 .009 'IT Vol C. Table 6.1.1.4 Table 6.1.1.5' H ? 0 64 0 0 'IT Vol C. Table 6.1.1.4 Table 6.1.1.5' O ? 0 8 .047 .032 'IT Vol C. Table 6.1.1.4 Table 6.1.1.5' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 .0531(3) -.1945(2) .1754(2) .0345(12) Uani ? ? ? ? ? C2 .2240(4) -.1982(3) .1262(2) .0464(15) Uani ? ? ? ? ? C3 .2020(5) -.3056(4) .0502(3) .063(2) Uani ? ? ? ? ? C4 -.0014(6) -.3071(4) -.0198(3) .073(2) Uani ? ? ? ? ? C5 -.1609(5) -.3232(3) .0390(3) .0601(18) Uani ? ? ? ? ? C6 -.1621(4) -.2116(2) .1104(2) .0411(13) Uani ? ? ? ? ? C7 -.2093(4) -.2498(3) .2129(3) .0498(15) Uani ? ? ? ? ? C8 -.1649(5) -.1272(3) .2742(3) .0546(17) Uani ? ? ? ? ? C9 .0346(4) -.0890(3) .2495(2) .0447(14) Uani ? ? ? ? ? O1 .0293(3) .03540(19) .2117(2) .0593(12) Uani ? ? ? ? ? C10 -.0047(4) -.3047(3) .2342(2) .0436(14) Uani ? ? ? ? ? O2 .0747(3) -.3981(2) .27468(19) .0634(13) Uani ? ? ? ? ? C11 -.2702(5) -.0994(3) .0549(3) .0577(18) Uani ? ? ? ? ? H21 .231(4) -.1167(16) .090(2) .052(8) Uiso ? ? ? ? ? H22 .337(3) -.213(3) .1843(17) .079(12) Uiso ? ? ? ? ? H31 .306(4) -.295(4) .011(2) .095(13) Uiso ? ? ? ? ? H32 .221(5) -.387(2) .089(2) .088(13) Uiso ? ? ? ? ? H41 -.021(5) -.2271(18) -.060(2) .065(10) Uiso ? ? ? ? ? H42 -.007(6) -.379(3) -.068(2) .103(14) Uiso ? ? ? ? ? H51 -.292(3) -.330(4) -.008(2) .107(15) Uiso ? ? ? ? ? H52 -.139(5) -.403(2) .079(2) .070(11) Uiso ? ? ? ? ? H7 -.323(3) -.302(2) .222(2) .059(9) Uiso ? ? ? ? ? H81 -.262(4) -.058(2) .252(3) .078(11) Uiso ? ? ? ? ? H82 -.146(4) -.143(3) .3473(9) .058(9) Uiso ? ? ? ? ? H111 -.217(5) -.074(4) -.004(2) .095(13) Uiso ? ? ? ? ? H112 -.388(5) -.136(5) .010(3) .16(2) Uiso ? ? ? ? ? H113 -.289(5) -.029(2) .100(2) .083(12) Uiso ? ? ? ? ? H9 .132(3) -.097(3) .3144(13) .057(9) Uiso ? ? ? ? ? H1o .145(5) .081(5) .210(5) .21(3) 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 C1 .0271(11) .0327(12) .0482(14) .0020(10) .0180(10) .0044(11) C2 .0396(15) .0442(16) .0647(19) .0015(12) .0314(14) .0036(14) C3 .060(2) .063(2) .075(2) .0108(17) .0387(18) -.0071(19) C4 .087(3) .075(3) .057(2) .009(2) .019(2) -.019(2) C5 .055(2) .051(2) .071(2) -.0018(15) .0064(17) -.0119(17) C6 .0332(13) .0330(13) .0581(17) -.0009(11) .0126(12) .0045(12) C7 .0344(14) .0396(15) .084(2) .0029(12) .0326(14) .0176(15) C8 .0475(17) .061(2) .066(2) .0092(14) .0349(16) .0034(16) C9 .0376(14) .0453(15) .0550(17) .0025(12) .0184(13) -.0031(13) O1 .0491(12) .0348(11) .0992(18) -.0007(9) .0274(12) -.0074(11) C10 .0365(14) .0394(14) .0594(17) .0031(12) .0207(12) .0109(13) O2 .0481(12) .0505(13) .0973(18) .0123(10) .0281(12) .0344(12) C11 .0517(18) .0494(19) .069(2) .0092(15) .0074(17) .0133(17) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter y(es) for value to be published C1 C2 2 2 1.502(4) ? C1 C10 2 2 1.522(4) ? C1 C9 2 2 1.534(4) ? C1 C6 2 2 1.583(3) ? C2 H21 2 2 1.00(2) ? C2 H22 2 2 1.00(2) ? C2 C3 2 2 1.526(5) ? C3 H32 2 2 1.00(3) ? C3 H31 2 2 1.01(3) ? C3 C4 2 2 1.532(5) ? C4 H41 2 2 1.00(2) ? C4 H42 2 2 1.00(3) ? C4 C5 2 2 1.528(6) ? C5 H52 2 2 1.00(2) ? C5 H51 2 2 1.00(2) ? C5 C6 2 2 1.535(5) ? C6 C11 2 2 1.518(4) ? C6 C7 2 2 1.568(5) ? C7 H7 2 2 1.00(2) ? C7 C10 2 2 1.516(4) ? C7 C8 2 2 1.538(5) ? C8 H81 2 2 1.00(3) ? C8 H82 2 2 .997(14) ? C8 C9 2 2 1.565(5) ? C9 H9 2 2 .998(18) ? C9 O1 2 2 1.411(4) ? O1 H1o 2 2 .95(5) ? C10 O2 2 2 1.206(3) ? C11 H113 2 2 .99(3) ? C11 H112 2 2 1.00(4) ? C11 H111 2 2 1.00(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter yes for value to be published C2 C1 C10 2 2 2 123.5(2) ? C2 C1 C9 2 2 2 120.7(2) ? C2 C1 C6 2 2 2 120.1(2) ? C10 C1 C9 2 2 2 97.6(2) ? C10 C1 C6 2 2 2 83.00(18) ? C9 C1 C6 2 2 2 104.2(2) ? H21 C2 H22 2 2 2 114(2) ? H21 C2 C1 2 2 2 109.3(17) ? H21 C2 C3 2 2 2 108.4(14) ? H22 C2 C1 2 2 2 102.5(15) ? H22 C2 C3 2 2 2 112(2) ? C1 C2 C3 2 2 2 110.9(2) ? H32 C3 H31 2 2 2 110(3) ? H32 C3 C2 2 2 2 107.4(18) ? H32 C3 C4 2 2 2 109(2) ? H31 C3 C2 2 2 2 108(2) ? H31 C3 C4 2 2 2 110.5(17) ? C2 C3 C4 2 2 2 112.0(3) ? H41 C4 H42 2 2 2 107(2) ? H41 C4 C5 2 2 2 111(2) ? H41 C4 C3 2 2 2 109.3(17) ? H42 C4 C5 2 2 2 110(2) ? H42 C4 C3 2 2 2 109(2) ? C5 C4 C3 2 2 2 111.1(3) ? H52 C5 H51 2 2 2 108(3) ? H52 C5 C4 2 2 2 110(2) ? H52 C5 C6 2 2 2 108.5(16) ? H51 C5 C4 2 2 2 110(2) ? H51 C5 C6 2 2 2 109(2) ? C4 C5 C6 2 2 2 111.1(3) ? C11 C6 C5 2 2 2 110.7(3) ? C11 C6 C7 2 2 2 118.0(3) ? C11 C6 C1 2 2 2 120.0(2) ? C5 C6 C7 2 2 2 114.0(2) ? C5 C6 C1 2 2 2 107.9(2) ? C7 C6 C1 2 2 2 83.68(19) ? H7 C7 C10 2 2 2 120.7(14) ? H7 C7 C8 2 2 2 117.6(17) ? H7 C7 C6 2 2 2 126.3(17) ? C10 C7 C8 2 2 2 98.6(2) ? C10 C7 C6 2 2 2 83.7(2) ? C8 C7 C6 2 2 2 102.5(2) ? H81 C8 H82 2 2 2 111(3) ? H81 C8 C7 2 2 2 114.1(16) ? H81 C8 C9 2 2 2 109.1(18) ? H82 C8 C7 2 2 2 111.8(18) ? H82 C8 C9 2 2 2 109.7(18) ? C7 C8 C9 2 2 2 100.4(3) ? H9 C9 O1 2 2 2 111.6(18) ? H9 C9 C1 2 2 2 112.6(17) ? H9 C9 C8 2 2 2 104.5(14) ? O1 C9 C1 2 2 2 115.7(3) ? O1 C9 C8 2 2 2 111.6(2) ? C1 C9 C8 2 2 2 99.7(2) ? H1o O1 C9 2 2 2 122(3) ? O2 C10 C7 2 2 2 136.2(3) ? O2 C10 C1 2 2 2 136.1(3) ? C7 C10 C1 2 2 2 87.6(2) ? H113 C11 H112 2 2 2 118(3) ? H113 C11 H111 2 2 2 115(3) ? H113 C11 C6 2 2 2 113.5(16) ? H112 C11 H111 2 2 2 90(3) ? H112 C11 C6 2 2 2 105(3) ? H111 C11 C6 2 2 2 112(2) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter yes for value to be published C6 C1 C2 C3 2 2 2 2 -43.5(3) ? C6 C1 C2 H21 2 2 2 2 76.0(14) ? C6 C1 C2 H22 2 2 2 2 -163(2) ? C9 C1 C2 C3 2 2 2 2 -175.8(2) ? C9 C1 C2 H21 2 2 2 2 -56.3(15) ? C9 C1 C2 H22 2 2 2 2 65(2) ? C10 C1 C2 C3 2 2 2 2 58.9(3) ? C10 C1 C2 H21 2 2 2 2 178.3(14) ? C10 C1 C2 H22 2 2 2 2 -60(2) ? C2 C1 C6 C5 2 2 2 2 45.3(3) ? C2 C1 C6 C7 2 2 2 2 158.6(2) ? C2 C1 C6 C11 2 2 2 2 -82.6(4) ? C9 C1 C6 C5 2 2 2 2 -175.7(2) ? C9 C1 C6 C7 2 2 2 2 -62.4(2) ? C9 C1 C6 C11 2 2 2 2 56.4(3) ? C10 C1 C6 C5 2 2 2 2 -79.5(3) ? C10 C1 C6 C7 2 2 2 2 33.8(2) ? C10 C1 C6 C11 2 2 2 2 152.6(3) ? C2 C1 C9 C8 2 2 2 2 178.4(2) ? C2 C1 C9 O1 2 2 2 2 58.6(3) ? C2 C1 C9 H9 2 2 2 2 -71.4(17) ? C6 C1 C9 C8 2 2 2 2 39.7(3) ? C6 C1 C9 O1 2 2 2 2 -80.1(3) ? C6 C1 C9 H9 2 2 2 2 150.0(17) ? C10 C1 C9 C8 2 2 2 2 -45.0(2) ? C10 C1 C9 O1 2 2 2 2 -164.8(2) ? C10 C1 C9 H9 2 2 2 2 65.3(17) ? C2 C1 C10 C7 2 2 2 2 -156.5(2) ? C2 C1 C10 O2 2 2 2 2 19.9(5) ? C6 C1 C10 C7 2 2 2 2 -34.9(2) ? C6 C1 C10 O2 2 2 2 2 141.4(4) ? C9 C1 C10 C7 2 2 2 2 68.6(2) ? C9 C1 C10 O2 2 2 2 2 -115.1(4) ? C1 C2 C3 C4 2 2 2 2 48.2(4) ? C1 C2 C3 H31 2 2 2 2 170(2) ? C1 C2 C3 H32 2 2 2 2 -71(2) ? H21 C2 C3 C4 2 2 2 2 -71.7(18) ? H21 C2 C3 H31 2 2 2 2 50(3) ? H21 C2 C3 H32 2 2 2 2 169(3) ? H22 C2 C3 C4 2 2 2 2 161.9(18) ? H22 C2 C3 H31 2 2 2 2 -76(3) ? H22 C2 C3 H32 2 2 2 2 43(3) ? C2 C3 C4 C5 2 2 2 2 -59.6(4) ? C2 C3 C4 H41 2 2 2 2 63(2) ? C2 C3 C4 H42 2 2 2 2 179(2) ? H31 C3 C4 C5 2 2 2 2 180(2) ? H31 C3 C4 H41 2 2 2 2 -57(3) ? H31 C3 C4 H42 2 2 2 2 59(3) ? H32 C3 C4 C5 2 2 2 2 59(2) ? H32 C3 C4 H41 2 2 2 2 -178(3) ? H32 C3 C4 H42 2 2 2 2 -62(3) ? C3 C4 C5 C6 2 2 2 2 62.6(4) ? C3 C4 C5 H51 2 2 2 2 -176(3) ? C3 C4 C5 H52 2 2 2 2 -57.6(16) ? H41 C4 C5 C6 2 2 2 2 -59.3(16) ? H41 C4 C5 H51 2 2 2 2 62(3) ? H41 C4 C5 H52 2 2 2 2 -179(2) ? H42 C4 C5 C6 2 2 2 2 -177(2) ? H42 C4 C5 H51 2 2 2 2 -56(3) ? H42 C4 C5 H52 2 2 2 2 63(3) ? C4 C5 C6 C1 2 2 2 2 -52.1(3) ? C4 C5 C6 C7 2 2 2 2 -143.1(3) ? C4 C5 C6 C11 2 2 2 2 81.0(3) ? H51 C5 C6 C1 2 2 2 2 -174(2) ? H51 C5 C6 C7 2 2 2 2 95(2) ? H51 C5 C6 C11 2 2 2 2 -41(2) ? H52 C5 C6 C1 2 2 2 2 69(2) ? H52 C5 C6 C7 2 2 2 2 -22(2) ? H52 C5 C6 C11 2 2 2 2 -158(2) ? C1 C6 C7 C8 2 2 2 2 63.6(2) ? C1 C6 C7 C10 2 2 2 2 -33.87(18) ? C1 C6 C7 H7 2 2 2 2 -157.7(18) ? C5 C6 C7 C8 2 2 2 2 170.4(2) ? C5 C6 C7 C10 2 2 2 2 72.9(2) ? C5 C6 C7 H7 2 2 2 2 -50.9(18) ? C11 C6 C7 C8 2 2 2 2 -57.2(3) ? C11 C6 C7 C10 2 2 2 2 -154.6(2) ? C11 C6 C7 H7 2 2 2 2 81.6(18) ? C1 C6 C11 H111 2 2 2 2 72(2) ? C1 C6 C11 H112 2 2 2 2 169(3) ? C1 C6 C11 H113 2 2 2 2 -60(2) ? C5 C6 C11 H111 2 2 2 2 -54(2) ? C5 C6 C11 H112 2 2 2 2 42(3) ? C5 C6 C11 H113 2 2 2 2 173(2) ? C7 C6 C11 H111 2 2 2 2 172(2) ? C7 C6 C11 H112 2 2 2 2 -92(3) ? C7 C6 C11 H113 2 2 2 2 39(2) ? C6 C7 C8 C9 2 2 2 2 -45.1(2) ? C6 C7 C8 H81 2 2 2 2 71(2) ? C6 C7 C8 H82 2 2 2 2 -161(2) ? C10 C7 C8 C9 2 2 2 2 40.3(3) ? C10 C7 C8 H81 2 2 2 2 157(2) ? C10 C7 C8 H82 2 2 2 2 -76(2) ? H7 C7 C8 C9 2 2 2 2 171.8(16) ? H7 C7 C8 H81 2 2 2 2 -72(3) ? H7 C7 C8 H82 2 2 2 2 55(2) ? C6 C7 C10 C1 2 2 2 2 35.22(18) ? C6 C7 C10 O2 2 2 2 2 -141.1(4) ? C8 C7 C10 C1 2 2 2 2 -66.5(2) ? C8 C7 C10 O2 2 2 2 2 117.2(4) ? H7 C7 C10 C1 2 2 2 2 164(2) ? H7 C7 C10 O2 2 2 2 2 -12(2) ? C7 C8 C9 C1 2 2 2 2 2.9(3) ? C7 C8 C9 O1 2 2 2 2 125.6(3) ? C7 C8 C9 H9 2 2 2 2 -113.7(18) ? H81 C8 C9 C1 2 2 2 2 -117(2) ? H81 C8 C9 O1 2 2 2 2 5(2) ? H81 C8 C9 H9 2 2 2 2 126(3) ? H82 C8 C9 C1 2 2 2 2 120.7(19) ? H82 C8 C9 O1 2 2 2 2 -116.6(19) ? H82 C8 C9 H9 2 2 2 2 4(3) ? C1 C9 O1 H1o 2 2 2 2 -84(5) ? C8 C9 O1 H1o 2 2 2 2 163(5) ? H9 C9 O1 H1o 2 2 2 2 46(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter yes for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- 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 H111 H112 1.42(6) 2 2 ? H51 H52 1.61(4) 2 2 ? H41 H42 1.61(3) 2 2 ? H81 H82 1.64(4) 2 2 ? H31 H32 1.65(5) 2 2 ? H21 H22 1.68(4) 2 2 ? H111 H113 1.68(5) 2 2 ? H112 H113 1.71(5) 2 2 ? O2 H1o 1.94(4) 2 . ? C1 H22 1.98(2) 2 2 ? O1 H9 2.01(2) 2 2 ? C6 H112 2.02(4) 2 2 ? C8 H9 2.06(2) 2 2 ? C6 C10 2.058(4) 2 2 ? C1 H21 2.06(3) 2 2 ? C2 H32 2.06(2) 2 2 ? C3 H21 2.069(18) 2 2 ? C2 H31 2.07(4) 2 2 ? C6 H52 2.08(2) 2 2 ? C9 H1o 2.08(6) 2 2 ? H81 H113 2.08(5) 2 2 ? C4 H32 2.08(3) 2 2 ? C3 H42 2.08(3) 2 2 ? C6 H51 2.09(4) 2 2 ? C3 H41 2.09(3) 2 2 ? C4 H52 2.09(3) 2 2 ? C5 H42 2.09(4) 2 2 ? C4 H51 2.10(2) 2 2 ? C1 C7 2.102(4) 2 2 ? C5 H41 2.11(3) 2 2 ? C4 H31 2.11(3) 2 2 ? C6 H111 2.11(3) 2 2 ? C9 H81 2.11(3) 2 2 ? C3 H22 2.11(3) 2 2 ? C9 H82 2.12(3) 2 2 ? C6 H113 2.12(3) 2 2 ? C7 H82 2.12(2) 2 2 ? C1 H9 2.13(2) 2 2 ? C7 H81 2.15(3) 2 2 ? H82 H9 2.15(4) 2 2 ? H51 H112 2.19(6) 2 2 ? C8 H7 2.19(2) 2 2 ? C10 H7 2.20(2) 2 2 ? H21 H31 2.30(4) 2 2 ? C9 C10 2.301(4) 2 2 ? H22 H32 2.30(4) 2 2 ? C6 H7 2.31(3) 2 2 ? C8 C10 2.315(4) 2 2 ? H21 H111 2.33(4) 2 4 ? H41 H111 2.36(5) 2 2 ? C10 H52 2.36(3) 2 2 ? C1 C8 2.368(5) 2 2 ? C7 C9 2.384(4) 2 2 ? H32 H42 2.38(4) 2 2 ? H9 H1o 2.39(7) 2 2 ? H42 H51 2.39(5) 2 2 ? H31 H42 2.39(5) 2 2 ? H31 H41 2.40(4) 2 2 ? H42 H52 2.42(5) 2 2 ? C6 C8 2.422(5) 2 2 ? H31 H82 2.43(4) 2 '3 556' ? H41 H51 2.43(4) 2 2 ? O1 H81 2.44(3) 2 2 ? C6 C9 2.460(4) 2 2 ? C8 O1 2.463(4) 2 2 ? C1 O1 2.494(3) 2 2 ? C1 C3 2.494(5) 2 2 ? H22 H31 2.50(4) 2 2 ? H51 H9 2.50(4) 2 '3 656' ? O1 H113 2.51(3) 2 2 ? H32 H52 2.51(5) 2 2 ? H22 H7 2.51(3) 2 '2 455' ? C5 C11 2.512(5) 2 2 ? C5 H112 2.52(4) 2 2 ? H7 H82 2.52(3) 2 2 ? C1 C5 2.521(4) 2 2 ? C3 C5 2.523(5) 2 2 ? C4 C6 2.527(5) 2 2 ? C7 O2 2.528(3) 2 2 ? C1 O2 2.533(3) 2 2 ? C2 C4 2.535(5) 2 2 ? O1 H7 2.54(3) 2 '1 665' ? C10 H9 2.54(3) 2 2 ? H42 H52 2.55(4) 2 '4 545' ? H41 H1o 2.56(6) 2 4 ? C7 H52 2.57(3) 2 2 ? C11 H51 2.58(4) 2 2 ? C8 H113 2.58(3) 2 2 ? H22 H1o 2.60(7) 2 . ? C5 C7 2.603(5) 2 2 ? H7 H81 2.63(4) 2 2 ? C2 C9 2.639(5) 2 2 ? C10 H82 2.64(3) 2 2 ? C7 C11 2.645(5) 2 2 ? C2 C10 2.664(5) 2 2 ? C5 C10 2.665(5) 2 2 ? H21 H41 2.67(3) 2 2 ? C2 C6 2.673(4) 2 2 ? H32 H9 2.68(4) 2 . ? C1 C11 2.687(4) 2 2 ? H42 H9 2.69(4) 2 '3 656' ? C5 H32 2.70(4) 2 2 ? C5 H111 2.70(4) 2 2 ? C3 H52 2.71(3) 2 2 ? C11 H81 2.73(4) 2 2 ? H31 H112 2.73(5) 2 '2 455' ? O2 H81 2.73(3) 2 '1 655' ? H81 H9 2.73(4) 2 2 ? H32 H1o 2.73(7) 2 . ? C6 H81 2.74(3) 2 2 ? C6 H41 2.74(3) 2 2 ? C10 H1o 2.74(4) 2 . ? H51 H111 2.75(6) 2 2 ? C1 H32 2.75(3) 2 2 ? C1 H52 2.76(2) 2 2 ? C2 H41 2.76(3) 2 2 ? O2 H52 2.77(3) 2 2 ? C9 H113 2.78(3) 2 2 ? H7 H81 2.78(4) 2 '1 655' ? H52 H7 2.79(4) 2 2 ? C7 H113 2.79(3) 2 2 ? C9 H22 2.81(3) 2 2 ? H21 H1o 2.81(7) 2 2 ? C10 H22 2.81(3) 2 2 ? H22 H9 2.81(4) 2 2 ? C4 H21 2.81(2) 2 2 ? H51 H82 2.83(3) 2 '3 656' ? O1 O2 2.832(3) 2 '1 565' ? C9 H21 2.84(3) 2 2 ? H21 H32 2.86(3) 2 2 ? H32 H42 2.88(4) 2 '4 545' ? C1 C4 2.877(5) 2 2 ? H32 H41 2.89(4) 2 2 ? O1 H41 2.90(3) 2 4 ? O1 H21 2.90(3) 2 2 ? O2 H7 2.90(2) 2 2 ? H7 H1o 2.91(6) 2 '1 655' ? H31 H51 2.91(4) 2 '2 455' ? H41 H52 2.91(4) 2 2 ? C4 H111 2.92(4) 2 2 ? C11 H41 2.93(3) 2 2 ? C10 H32 2.95(4) 2 2 ? C8 C11 2.949(5) 2 2 ? O2 H32 2.96(4) 2 2 ? C7 H9 2.96(2) 2 2 ? C1 H113 2.97(3) 2 2 ? H111 H1o 2.98(7) 2 4 ? H112 H113 2.98(5) 2 '4 655' ? C5 H7 2.99(3) 2 2 ? C2 H9 2.99(2) 2 2 ? C1 H1o 3.00(6) 2 2 ? C6 H21 3.00(3) 2 2 ? C2 C5 3.005(4) 2 2 ? O1 C11 3.010(4) 2 2 ? C1 H81 3.02(3) 2 2 ? O1 H32 3.02(3) 2 '1 565' ? H42 H82 3.02(5) 2 '3 556' ? C3 C6 3.023(5) 2 2 ? C9 C11 3.028(4) 2 2 ? C1 H111 3.03(3) 2 2 ? C7 H112 3.04(4) 2 2 ? C1 H82 3.05(2) 2 2 ? H52 H81 3.05(4) 2 '1 655' ? O1 H22 3.07(3) 2 '1 565' ? C1 H7 3.07(2) 2 2 ? C7 H51 3.07(3) 2 2 ? O2 H111 3.08(3) 2 3 ? O2 H21 3.08(2) 2 . ? C11 H21 3.09(2) 2 4 ? O1 H82 3.09(3) 2 2 ? H41 H112 3.09(5) 2 2 ? C6 O1 3.118(3) 2 2 ? H21 H112 3.12(5) 2 '2 455' ? O2 H22 3.13(3) 2 2 ? H21 H113 3.13(4) 2 4 ? C7 H22 3.14(2) 2 '2 655' ? H21 H111 3.15(4) 2 2 ? H32 H52 3.16(4) 2 '4 545' ? H42 H42 3.17(4) 2 '4 545' ? C10 H81 3.17(3) 2 '1 655' ? C6 O2 3.171(3) 2 2 ? C2 O1 3.172(4) 2 2 ? C1 H41 3.17(3) 2 2 ? C3 C10 3.179(5) 2 2 ? C4 H9 3.20(2) 2 '3 656' ? O2 H112 3.20(4) 2 3 ? H22 H81 3.21(4) 2 '2 455' ? C4 C11 3.208(6) 2 2 ? C10 H81 3.21(3) 2 2 ? C5 H9 3.212(18) 2 '3 656' ? C11 H7 3.22(3) 2 2 ? H51 H7 3.22(5) 2 2 ? C2 H1o 3.23(6) 2 . ? O2 H113 3.23(4) 2 '1 655' ? H52 H82 3.23(4) 2 '1 655' ? O2 H9 3.23(3) 2 2 ? H41 H9 3.24(4) 2 '3 656' ? C3 H82 3.24(2) 2 '3 556' ? H112 H112 3.26(7) 2 '4 655' ? C2 H1o 3.26(6) 2 2 ? C2 O2 3.266(4) 2 2 ? H32 H51 3.27(5) 2 '4 545' ? C9 H32 3.27(3) 2 '1 565' ? O1 H111 3.29(3) 2 2 ? C9 O2 3.291(4) 2 2 ? C2 H52 3.29(3) 2 2 ? H113 H1o 3.30(5) 2 2 ? H21 H9 3.30(3) 2 2 ? H21 H112 3.31(5) 2 4 ? C6 H82 3.307(15) 2 2 ? C7 H81 3.31(3) 2 '1 655' ? C6 H9 3.31(2) 2 2 ? C8 O2 3.319(4) 2 2 ? C9 H7 3.33(2) 2 2 ? C1 H1o 3.33(5) 2 . ? C2 H111 3.33(4) 2 4 ? C11 H52 3.33(2) 2 2 ? C6 H32 3.34(3) 2 2 ? H52 H112 3.34(5) 2 2 ? C1 H31 3.34(4) 2 2 ? C2 H7 3.34(2) 2 '2 455' ? H7 H112 3.35(5) 2 2 ? H81 H112 3.35(5) 2 2 ? C8 H1o 3.35(5) 2 2 ? C5 H42 3.36(3) 2 '4 545' ? C4 H112 3.36(4) 2 2 ? O2 H9 3.36(3) 2 . ? O2 H82 3.37(3) 2 2 ? H42 H81 3.37(5) 2 '3 556' ? C4 H52 3.38(2) 2 '4 545' ? H81 H1o 3.38(6) 2 2 ? H7 H113 3.38(4) 2 2 ? C5 O2 3.382(4) 2 2 ? H7 H113 3.39(4) 2 '1 655' ? C2 H42 3.39(3) 2 2 ? C3 H51 3.39(2) 2 2 ? C1 H51 3.39(3) 2 2 ? C4 H22 3.39(2) 2 2 ? C9 H51 3.39(3) 2 3 ? C6 H42 3.39(4) 2 2 ? C5 H113 3.40(3) 2 2 ? C5 H31 3.40(3) 2 2 ? C8 H31 3.40(4) 2 '3 655' ? O2 H22 3.41(3) 2 . ? H111 H111 3.41(5) 2 4 ? O1 H111 3.42(3) 2 4 ? C6 H22 3.42(2) 2 2 ? C11 H112 3.43(4) 2 '4 655' ? H32 H7 3.43(4) 2 '2 455' ? C9 H7 3.44(3) 2 '1 665' ? H22 H1o 3.44(6) 2 2 ? C8 H7 3.44(3) 2 '1 665' ? H31 H7 3.44(4) 2 '2 455' ? C3 H1o 3.44(6) 2 . ? C4 H82 3.44(3) 2 '3 556' ? H82 H112 3.45(5) 2 3 ? C11 H21 3.45(3) 2 2 ? C7 O1 3.450(4) 2 2 ? H41 H82 3.45(4) 2 '3 556' ? C5 H21 3.46(2) 2 2 ? H22 H42 3.46(4) 2 3 ? C1 H112 3.46(3) 2 2 ? C2 H111 3.47(3) 2 2 ? C10 H21 3.47(3) 2 2 ? H21 H113 3.47(5) 2 '2 455' ? O1 H22 3.47(3) 2 2 ? O2 H41 3.48(3) 2 3 ? C9 O2 3.480(4) 2 '1 565' ? H22 H41 3.49(4) 2 3 ? C10 H51 3.49(3) 2 2 ? H22 H112 3.49(5) 2 '2 455' ? C4 C10 3.490(5) 2 2 ? C10 C11 3.492(4) 2 2 ? C7 H111 3.50(3) 2 2 ? H51 H113 3.51(5) 2 2 ? C5 H32 3.51(3) 2 '4 545' ? C7 O1 3.507(4) 2 '1 655' ? C2 H112 3.51(4) 2 '2 455' ? C4 H1o 3.51(6) 2 4 ? H31 H52 3.53(4) 2 '4 545' ? C4 H42 3.53(3) 2 '4 545' ? C3 O2 3.531(5) 2 2 ? C3 H112 3.53(4) 2 '2 455' ? C9 H111 3.54(3) 2 2 ? C3 H52 3.54(2) 2 '4 545' ? H82 H113 3.54(3) 2 2 ? C8 H51 3.54(3) 2 3 ? H111 H112 3.54(6) 2 '4 655' ? C2 C11 3.544(4) 2 2 ? C2 C7 3.546(5) 2 2 ? C8 H22 3.55(2) 2 '2 655' ? C11 H31 3.56(3) 2 '2 655' ? C8 H42 3.57(4) 2 '3 655' ? H41 H7 3.58(4) 2 '3 556' ? C8 H52 3.58(3) 2 '1 665' ? H41 H113 3.59(4) 2 4 ? H111 H113 3.59(5) 2 '4 655' ? H81 H111 3.60(5) 2 2 ? C11 H113 3.60(3) 2 '4 655' ? H32 H51 3.60(4) 2 2 ? H113 H113 3.61(4) 2 '4 655' ? C2 O2 3.613(4) 2 '1 565' ? H41 H111 3.62(4) 2 4 ? C4 H32 3.62(2) 2 '4 545' ? C8 H112 3.62(4) 2 2 ? O1 C10 3.621(3) 2 2 ? C9 H42 3.62(3) 2 3 ? H52 H9 3.63(3) 2 '3 656' ? C3 H7 3.63(2) 2 '2 455' ? O2 H42 3.63(3) 2 '4 545' ? C3 H42 3.63(3) 2 '4 545' ? H31 H52 3.64(5) 2 2 ? C11 H21 3.64(3) 2 '2 655' ? C3 H9 3.66(3) 2 . ? O1 C10 3.665(3) 2 '1 565' ? C5 H31 3.68(3) 2 '2 655' ? C8 O2 3.705(4) 2 '1 665' ? C11 H1o 3.73(5) 2 2 ? C10 H112 3.74(4) 2 3 ? O2 C11 3.756(5) 2 3 ? C2 O1 3.762(4) 2 . ? C3 H111 3.77(4) 2 2 ? C10 H113 3.78(3) 2 2 ? C6 H31 3.78(3) 2 '2 655' ? C3 O1 3.783(4) 2 . ? O2 H51 3.79(4) 2 3 ? C11 H22 3.79(3) 2 '2 655' ? C10 H113 3.79(3) 2 '1 655' ? C8 H111 3.79(3) 2 2 ? C10 H51 3.80(3) 2 3 ? C5 H22 3.80(2) 2 2 ? C1 H42 3.81(3) 2 2 ? C3 H51 3.81(3) 2 '2 455' ? C5 C9 3.819(5) 2 2 ? C2 C8 3.822(5) 2 2 ? C5 H82 3.83(2) 2 '3 656' ? C5 C8 3.841(5) 2 2 ? C4 C7 3.843(6) 2 2 ? C6 H1o 3.85(5) 2 2 ? C11 C11 3.862(5) 2 '4 655' ? C6 H22 3.87(3) 2 '2 655' ? C4 O1 3.872(5) 2 4 ? C7 H1o 3.89(5) 2 '1 655' ? C7 H31 3.91(3) 2 '2 655' ? C7 H113 3.91(3) 2 '1 655' ? C10 H41 3.92(3) 2 3 ? C10 H111 3.92(3) 2 3 ? C5 H81 3.92(3) 2 '1 655' ? C2 C7 3.926(4) 2 '2 455' ? C2 H81 3.93(3) 2 '2 455' ? C11 H1o 3.93(7) 2 4 ? C6 H31 3.93(3) 2 2 ? C2 H51 3.93(2) 2 2 ? C11 H82 3.939(13) 2 2 ? C9 H112 3.94(4) 2 2 ? C3 C9 3.941(5) 2 2 ? C2 H113 3.95(4) 2 '2 455' ? C7 H22 3.96(3) 2 2 ? C11 H111 3.96(4) 2 '4 655' ? C2 H113 3.96(3) 2 2 ? C3 H51 3.97(4) 2 '4 545' ? C4 H22 3.97(2) 2 '3 656' ? C3 C11 3.979(5) 2 2 ? C8 H52 3.99(3) 2 2 ? O1 H112 3.99(4) 2 2 ? C11 H41 4.00(2) 2 4 ? C1 H111 4.02(4) 2 4 ? C11 H9 4.020(18) 2 2 ? C2 H113 4.02(3) 2 4 ? C2 C11 4.024(5) 2 '2 455' ? C10 H112 4.03(4) 2 2 ? C1 O2 4.039(3) 2 '1 565' ? C2 C11 4.066(5) 2 4 ? C3 C7 4.067(5) 2 2 ? C4 O2 4.071(5) 2 2 ? C4 C5 4.095(6) 2 '4 545' ? O2 C11 4.097(5) 2 '1 655' ? C7 C8 4.099(4) 2 '1 655' ? C3 C5 4.101(5) 2 '4 545' ? C8 C10 4.110(4) 2 '1 665' ? C4 C4 4.113(6) 2 '4 545' ? C4 C8 4.126(6) 2 '3 556' ? C1 O1 4.137(3) 2 . ? C4 C9 4.152(5) 2 '3 656' ? C3 C8 4.159(6) 2 '3 556' ? C5 C9 4.174(4) 2 '3 656' ? C3 C9 4.205(5) 2 . ? C4 O2 4.215(4) 2 '3 656' ? O1 C10 4.263(4) 2 '1 665' ? C3 C7 4.276(4) 2 '2 455' ? C3 C11 4.285(5) 2 '2 455' ? C4 C9 4.315(5) 2 2 ? C3 C4 4.319(6) 2 '4 545' ? O1 O2 4.340(3) 2 '1 665' ? C7 C9 4.343(4) 2 '1 655' ? C2 C6 4.363(4) 2 '2 455' ? C5 O2 4.367(4) 2 '3 656' ? C2 C8 4.381(4) 2 '2 455' ? C9 C10 4.431(4) 2 '1 565' ? _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 392 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 3 1 0 0 4 loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _reflns_number_observed ? _reflns_d_resolution_high .799 _reflns_d_resolution_low 8.294 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_theta_min 5.33 _diffrn_reflns_reduction_process 'perpendicular monochr Lp' _diffrn_ambient_temperature 293 _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_radiation_detector ? _refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970' _refine_ls_matrix_type full _refine_ls_number_restraints 16 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .078 _refine_ls_wR_factor_all .066 _refine_ls_goodness_of_fit_all 1.031 _refine_ls_shift/su_mean .002 #-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end