# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jack Baldwin' _publ_contact_author_address ; Organic Chemistry University of Oxford The Chemistry Research Laboratory Mansfield Road Oxford OX13TA UNITED KINGDOM ; _publ_contact_author_email JACK.BALDWIN@CHEM.OX.AC.UK _publ_section_title ; A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (+-)-lucidene and (+-)-Alboatrin ; loop_ _publ_author_name 'J. Baldwin' 'Robert M. Adlington' 'John Moses' 'Raphael Rodriguez' data_1 _database_code_depnum_ccdc_archive 'CCDC 237660' _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The OH hydrogen atom was located in a difference Fourier map and its coordinates and isotropic thermal parameter subsequently refined. Other H atoms were positioned geometrically, the preferred orientations of the methyl groups having benn previously identified by examination of the difference Fourier map ; #============================================================= _cell_length_a 29.1890(14) _cell_angle_alpha 90 _cell_length_b 4.9244(3) _cell_angle_beta 123.921(2) _cell_length_c 19.8157(11) _cell_angle_gamma 90 _cell_volume 2363.5(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C12 H14 O5 ' _chemical_formula_moiety ' C12 H14 O5 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 238.24 _cell_measurement_reflns_used 11482 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.105 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 11482 _reflns_number_total 2683 #2983 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_min 5.131 _diffrn_reflns_theta_max 27.493 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.493 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -37 _reflns_limit_h_max 31 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _refine_diff_density_min -0.31 _refine_diff_density_max 0.29 _refine_ls_number_reflns 1691 _refine_ls_number_restraints 0 _refine_ls_number_parameters 158 #_refine_ls_R_factor_ref 0.0483 _refine_ls_wR_factor_ref 0.0599 _refine_ls_goodness_of_fit_ref 1.0723 #_reflns_number_all 2683 _refine_ls_R_factor_all 0.0782 _refine_ls_wR_factor_all 0.0712 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1691 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_gt 0.0599 _refine_ls_shift/su_max 0.008849 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.33 0.897 0.913 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type C1 C 0.35363(8) 0.1802(4) 0.37123(11) 0.0294 1.0000 Uani C2 C 0.32513(8) 0.0988(4) 0.29098(11) 0.0299 1.0000 Uani C3 C 0.33895(8) 0.2235(4) 0.24146(11) 0.0302 1.0000 Uani C4 C 0.38008(8) 0.4243(4) 0.27183(12) 0.0308 1.0000 Uani C5 C 0.40819(8) 0.5005(4) 0.35391(12) 0.0305 1.0000 Uani C6 C 0.39428(8) 0.3768(4) 0.40357(11) 0.0308 1.0000 Uani O1 O 0.34334(6) 0.0438(3) 0.42424(8) 0.0324 1.0000 Uani C7 C 0.30105(8) 0.1328(4) 0.42732(11) 0.0318 1.0000 Uani O2 O 0.27200(7) 0.3177(4) 0.38532(10) 0.0483 1.0000 Uani C8 C 0.29665(9) -0.0191(5) 0.48837(12) 0.0376 1.0000 Uani O3 O 0.31369(6) 0.1549(3) 0.16156(8) 0.0396 1.0000 Uani C9 C 0.39138(9) 0.5492(4) 0.21342(13) 0.0357 1.0000 Uani O4 O 0.42440(6) 0.3561(3) 0.20183(8) 0.0366 1.0000 Uani C10 C 0.42232(8) 0.3795(4) 0.13291(12) 0.0334 1.0000 Uani O5 O 0.39649(9) 0.5544(3) 0.08334(10) 0.0519 1.0000 Uani C11 C 0.45511(10) 0.1623(4) 0.12542(14) 0.0401 1.0000 Uani C12 C 0.45299(9) 0.7129(4) 0.38966(14) 0.0390 1.0000 Uani H1 H 0.2842(13) 0.035(6) 0.1431(18) 0.064(9) 1.0000 Uiso H21 H 0.2958 -0.0438 0.2693 0.0361 1.0000 Uiso H61 H 0.4136 0.4302 0.4620 0.0356 1.0000 Uiso H81 H 0.2648 0.0527 0.4889 0.0465 1.0000 Uiso H82 H 0.3315 0.0041 0.5435 0.0465 1.0000 Uiso H83 H 0.2907 -0.2162 0.4738 0.0465 1.0000 Uiso H91 H 0.4122 0.7230 0.2363 0.0443 1.0000 Uiso H92 H 0.3558 0.5861 0.1603 0.0443 1.0000 Uiso H111 H 0.4525 0.1867 0.0733 0.0498 1.0000 Uiso H112 H 0.4946 0.1751 0.1722 0.0498 1.0000 Uiso H113 H 0.4401 -0.0198 0.1257 0.0498 1.0000 Uiso H121 H 0.4679 0.7383 0.4485 0.0447 1.0000 Uiso H122 H 0.4834 0.6527 0.3840 0.0447 1.0000 Uiso H123 H 0.4374 0.8885 0.3602 0.0447 1.0000 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0322(9) 0.0306(9) 0.0273(9) 0.0046(8) 0.0179(8) 0.0050(8) C2 0.0311(9) 0.0327(9) 0.0264(9) -0.0010(8) 0.0164(8) -0.0013(8) C3 0.0291(9) 0.0359(10) 0.0238(9) -0.0016(8) 0.0137(7) 0.0003(8) C4 0.0319(9) 0.0308(9) 0.0324(9) 0.0035(8) 0.0197(8) 0.0039(8) C5 0.0287(9) 0.0267(9) 0.0346(10) -0.0004(8) 0.0167(8) 0.0030(8) C6 0.0311(9) 0.0311(9) 0.0269(9) -0.0011(7) 0.0142(8) 0.0033(8) O1 0.0387(7) 0.0336(7) 0.0288(7) 0.0057(6) 0.0213(6) 0.0052(6) C7 0.0326(9) 0.0353(10) 0.0257(9) -0.0011(8) 0.0153(8) -0.0010(8) O2 0.0480(9) 0.0574(10) 0.0478(9) 0.0199(8) 0.0318(8) 0.0208(8) C8 0.0406(11) 0.0442(12) 0.0315(10) 0.0016(9) 0.0223(9) -0.0039(10) O3 0.0407(8) 0.0531(9) 0.0246(7) -0.0050(7) 0.0180(6) -0.0086(7) C9 0.0368(10) 0.0375(10) 0.0365(10) 0.0068(9) 0.0229(9) 0.0044(9) O4 0.0355(7) 0.0463(8) 0.0322(7) 0.0085(6) 0.0215(6) 0.0090(6) C10 0.0378(10) 0.0321(9) 0.0296(9) -0.0049(8) 0.0185(8) -0.0097(8) O5 0.0841(13) 0.0378(8) 0.0405(8) 0.0095(7) 0.0389(9) 0.0095(9) C11 0.0443(11) 0.0400(11) 0.0401(11) -0.0064(9) 0.0261(10) -0.0044(10) C12 0.0346(10) 0.0332(10) 0.0439(11) -0.0021(9) 0.0186(9) -0.0027(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.380(3) yes C1 . C6 . 1.381(3) yes C1 . O1 . 1.413(2) yes C2 . C3 . 1.394(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.406(3) yes C3 . O3 . 1.364(2) yes C4 . C5 . 1.404(3) yes C4 . C9 . 1.501(3) yes C5 . C6 . 1.396(3) yes C5 . C12 . 1.507(3) yes C6 . H61 . 1.000 no O1 . C7 . 1.343(2) yes C7 . O2 . 1.205(3) yes C7 . C8 . 1.488(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C8 . H83 . 1.000 no O3 . H1 . 0.94(3) yes C9 . O4 . 1.461(3) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no O4 . C10 . 1.338(2) yes C10 . O5 . 1.204(3) yes C10 . C11 . 1.497(3) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 123.21(17) yes C2 . C1 . O1 . 118.46(17) yes C6 . C1 . O1 . 118.19(16) yes C1 . C2 . C3 . 117.24(17) yes C1 . C2 . H21 . 121.381 no C3 . C2 . H21 . 121.381 no C2 . C3 . C4 . 121.47(17) yes C2 . C3 . O3 . 121.77(17) yes C4 . C3 . O3 . 116.75(18) yes C3 . C4 . C5 . 119.43(18) yes C3 . C4 . C9 . 117.46(17) yes C5 . C4 . C9 . 123.11(18) yes C4 . C5 . C6 . 119.23(18) yes C4 . C5 . C12 . 121.53(18) yes C6 . C5 . C12 . 119.24(18) yes C1 . C6 . C5 . 119.42(17) yes C1 . C6 . H61 . 120.292 no C5 . C6 . H61 . 120.292 no C1 . O1 . C7 . 117.42(15) yes O1 . C7 . O2 . 121.71(18) yes O1 . C7 . C8 . 111.80(17) yes O2 . C7 . C8 . 126.48(19) yes C7 . C8 . H81 . 109.467 no C7 . C8 . H82 . 109.467 no H81 . C8 . H82 . 109.476 no C7 . C8 . H83 . 109.466 no H81 . C8 . H83 . 109.476 no H82 . C8 . H83 . 109.476 no C3 . O3 . H1 . 113.2(18) yes C4 . C9 . O4 . 107.61(16) yes C4 . C9 . H91 . 109.935 no O4 . C9 . H91 . 109.935 no C4 . C9 . H92 . 109.935 no O4 . C9 . H92 . 109.935 no H91 . C9 . H92 . 109.467 no C9 . O4 . C10 . 116.52(15) yes O4 . C10 . O5 . 123.1(2) yes O4 . C10 . C11 . 111.88(17) yes O5 . C10 . C11 . 125.05(19) yes C10 . C11 . H111 . 109.467 no C10 . C11 . H112 . 109.467 no H111 . C11 . H112 . 109.476 no C10 . C11 . H113 . 109.467 no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C5 . C12 . H121 . 109.467 no C5 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no C5 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _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 O3 H1 O2 7_545 0.94(3) 1.77(3) 2.699(2) 175(3) yes data_arc793 _database_code_depnum_ccdc_archive 'CCDC 239363' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The OH hydrogen atoms were located in a difference Fourier map which clearly showed them both to be disordered over two positions. Symmetry considerations require that the occupancies of these sites are 0.5. The coordaintes of the OH hydrogen atoms were reined subject to restraint of the O-H distances to 0.85(10) \%A. A common isotropic thermal parameter was refined for these atoms. Other hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been previously determined by examination of a difference Fourier map ; #============================================================= _cell_length_a 19.4765(3) _cell_angle_alpha 90 _cell_length_b 9.6966(2) _cell_angle_beta 94.5151(8) _cell_length_c 21.0587(4) _cell_angle_gamma 90 _cell_volume 3964.72(13) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C23 H32 O2 ' _chemical_formula_moiety ' C23 H32 O2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 340.51 _cell_measurement_reflns_used 32823 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.071 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 32823 _reflns_number_total 9000 #9525 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_theta_min 5.116 _diffrn_reflns_theta_max 27.466 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.466 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -25 _reflns_limit_h_max 25 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _refine_diff_density_min -0.33 _refine_diff_density_max 0.28 _refine_ls_number_reflns 5437 _refine_ls_number_restraints 4 _refine_ls_number_parameters 464 #_refine_ls_R_factor_ref 0.0432 _refine_ls_wR_factor_ref 0.0524 _refine_ls_goodness_of_fit_ref 1.1038 #_reflns_number_all 8996 _refine_ls_R_factor_all 0.0853 _refine_ls_wR_factor_all 0.0695 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 5437 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_gt 0.0524 _refine_ls_shift/su_max 0.007881 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.975 0.696 0.640 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_disorder_group O1 O 0.54330(6) 0.22396(12) 0.26450(6) 0.0283 1.0000 Uani . . C1 C 0.56159(8) 0.25226(18) 0.19960(8) 0.0257 1.0000 Uani . . C2 C 0.56353(9) 0.10531(19) 0.17175(9) 0.0299 1.0000 Uani . . C3 C 0.62250(9) 0.02275(17) 0.20233(8) 0.0276 1.0000 Uani . . C4 C 0.66992(9) -0.04036(18) 0.17128(8) 0.0279 1.0000 Uani . . C5 C 0.73804(9) -0.09833(18) 0.19908(8) 0.0275 1.0000 Uani . . C6 C 0.79543(9) -0.01658(19) 0.16699(9) 0.0328 1.0000 Uani . . C7 C 0.78280(9) 0.13661(19) 0.16836(9) 0.0308 1.0000 Uani . . C8 C 0.75736(10) 0.21303(19) 0.11971(9) 0.0336 1.0000 Uani . . C9 C 0.73215(10) 0.35872(19) 0.12938(9) 0.0336 1.0000 Uani . . C10 C 0.65351(9) 0.36125(18) 0.13431(8) 0.0297 1.0000 Uani . . C11 C 0.63233(8) 0.32419(17) 0.20116(7) 0.0234 1.0000 Uani . . C12 C 0.63443(8) 0.45228(17) 0.24354(8) 0.0254 1.0000 Uani . . C13 C 0.60390(8) 0.42785(16) 0.30603(7) 0.0220 1.0000 Uani . . C14 C 0.61832(8) 0.51407(17) 0.35886(8) 0.0243 1.0000 Uani . . C15 C 0.58728(9) 0.49108(18) 0.41507(8) 0.0275 1.0000 Uani . . C16 C 0.54036(9) 0.38429(18) 0.41833(8) 0.0285 1.0000 Uani . . C17 C 0.52565(9) 0.29638(17) 0.36754(8) 0.0269 1.0000 Uani . . C18 C 0.55825(8) 0.31842(16) 0.31160(8) 0.0231 1.0000 Uani . . C19 C 0.50380(9) 0.3387(2) 0.16682(9) 0.0366 1.0000 Uani . . C20 C 0.74842(11) -0.0798(2) 0.27109(9) 0.0367 1.0000 Uani . . C21 C 0.74461(11) -0.2511(2) 0.18217(9) 0.0364 1.0000 Uani . . C22 C 0.74622(14) 0.1629(3) 0.05210(10) 0.0547 1.0000 Uani . . C23 C 0.66653(9) 0.6346(2) 0.35430(10) 0.0365 1.0000 Uani . . O2 O 0.50723(9) 0.36780(17) 0.47357(8) 0.0492 1.0000 Uani D . O3 O 0.21870(5) 0.25526(12) 0.49621(5) 0.0245 1.0000 Uani . . C24 C 0.14560(8) 0.22058(18) 0.49828(8) 0.0251 1.0000 Uani . . C25 C 0.11113(9) 0.36396(19) 0.49703(8) 0.0301 1.0000 Uani . . C26 C 0.12585(9) 0.44509(18) 0.55757(9) 0.0294 1.0000 Uani . . C27 C 0.07784(9) 0.49567(19) 0.59224(9) 0.0323 1.0000 Uani . . C28 C 0.08693(10) 0.55799(19) 0.65841(9) 0.0341 1.0000 Uani . . C29 C 0.04507(10) 0.4658(2) 0.70262(10) 0.0388 1.0000 Uani . . C30 C 0.05842(9) 0.3148(2) 0.69232(9) 0.0327 1.0000 Uani . . C31 C 0.01695(9) 0.2270(2) 0.65965(10) 0.0359 1.0000 Uani . . C32 C 0.04245(9) 0.08918(19) 0.63766(9) 0.0323 1.0000 Uani . . C33 C 0.05979(8) 0.09811(19) 0.56724(9) 0.0298 1.0000 Uani . . C34 C 0.13525(8) 0.13971(17) 0.55974(8) 0.0232 1.0000 Uani . . C35 C 0.18037(8) 0.01046(17) 0.56381(8) 0.0239 1.0000 Uani . . C36 C 0.25258(8) 0.03611(16) 0.54556(7) 0.0212 1.0000 Uani . . C37 C 0.30599(8) -0.05777(16) 0.56095(7) 0.0226 1.0000 Uani . . C38 C 0.37180(8) -0.03220(17) 0.54247(8) 0.0253 1.0000 Uani . . C39 C 0.38481(8) 0.08629(17) 0.50836(7) 0.0230 1.0000 Uani . . C40 C 0.33297(8) 0.18060(16) 0.49229(7) 0.0215 1.0000 Uani . . C41 C 0.26703(8) 0.15439(16) 0.51151(7) 0.0211 1.0000 Uani . . C42 C 0.12275(9) 0.1404(2) 0.43804(8) 0.0332 1.0000 Uani . . C43 C 0.16198(11) 0.5628(2) 0.68458(10) 0.0424 1.0000 Uani . . C44 C 0.05658(13) 0.7045(2) 0.65725(12) 0.0523 1.0000 Uani . . C45 C -0.05626(11) 0.2578(3) 0.63613(14) 0.0603 1.0000 Uani . . C46 C 0.29306(9) -0.18652(18) 0.59866(8) 0.0287 1.0000 Uani . . O4 O 0.45048(6) 0.10848(16) 0.48987(7) 0.0336 1.0000 Uani D . H1 H 0.493(3) 0.297(5) 0.479(2) 0.045(7) 0.5000 Uiso D -1 H2 H 0.496(3) 0.443(4) 0.488(2) 0.045(7) 0.5000 Uiso D -2 H3 H 0.461(2) 0.189(5) 0.481(2) 0.045(7) 0.5000 Uiso D -2 H4 H 0.483(2) 0.053(5) 0.496(2) 0.045(7) 0.5000 Uiso D -1 H21 H 0.5686 0.1118 0.1250 0.0360 1.0000 Uiso . . H22 H 0.5194 0.0574 0.1790 0.0360 1.0000 Uiso . . H31 H 0.6262 0.0149 0.2498 0.0334 1.0000 Uiso . . H41 H 0.6597 -0.0510 0.1243 0.0335 1.0000 Uiso . . H61 H 0.8410 -0.0369 0.1903 0.0397 1.0000 Uiso . . H62 H 0.7961 -0.0471 0.1217 0.0397 1.0000 Uiso . . H71 H 0.7946 0.1852 0.2097 0.0374 1.0000 Uiso . . H91 H 0.7556 0.3969 0.1695 0.0411 1.0000 Uiso . . H92 H 0.7436 0.4169 0.0925 0.0411 1.0000 Uiso . . H101 H 0.6362 0.4560 0.1233 0.0357 1.0000 Uiso . . H102 H 0.6317 0.2935 0.1031 0.0357 1.0000 Uiso . . H111 H 0.6667 0.2558 0.2198 0.0281 1.0000 Uiso . . H121 H 0.6835 0.4814 0.2524 0.0307 1.0000 Uiso . . H122 H 0.6080 0.5277 0.2203 0.0307 1.0000 Uiso . . H151 H 0.5987 0.5513 0.4530 0.0331 1.0000 Uiso . . H171 H 0.4924 0.2186 0.3707 0.0328 1.0000 Uiso . . H191 H 0.5148 0.3598 0.1223 0.0436 1.0000 Uiso . . H192 H 0.4992 0.4267 0.1908 0.0436 1.0000 Uiso . . H193 H 0.4596 0.2861 0.1659 0.0436 1.0000 Uiso . . H201 H 0.7939 -0.1196 0.2870 0.0440 1.0000 Uiso . . H202 H 0.7474 0.0206 0.2817 0.0440 1.0000 Uiso . . H203 H 0.7107 -0.1284 0.2918 0.0440 1.0000 Uiso . . H211 H 0.7898 -0.2872 0.2010 0.0440 1.0000 Uiso . . H212 H 0.7420 -0.2618 0.1348 0.0440 1.0000 Uiso . . H213 H 0.7063 -0.3042 0.1997 0.0440 1.0000 Uiso . . H221 H 0.7640 0.0665 0.0493 0.0667 1.0000 Uiso . . H222 H 0.7714 0.2244 0.0237 0.0667 1.0000 Uiso . . H223 H 0.6959 0.1645 0.0384 0.0667 1.0000 Uiso . . H231 H 0.6710 0.6847 0.3959 0.0443 1.0000 Uiso . . H232 H 0.7128 0.6004 0.3440 0.0443 1.0000 Uiso . . H233 H 0.6478 0.6986 0.3200 0.0443 1.0000 Uiso . . H251 H 0.0602 0.3511 0.4897 0.0363 1.0000 Uiso . . H252 H 0.1282 0.4181 0.4610 0.0363 1.0000 Uiso . . H261 H 0.1751 0.4619 0.5726 0.0354 1.0000 Uiso . . H271 H 0.0296 0.4923 0.5723 0.0389 1.0000 Uiso . . H291 H 0.0588 0.4895 0.7481 0.0473 1.0000 Uiso . . H292 H -0.0052 0.4845 0.6931 0.0473 1.0000 Uiso . . H301 H 0.1029 0.2769 0.7120 0.0398 1.0000 Uiso . . H321 H 0.0848 0.0624 0.6648 0.0394 1.0000 Uiso . . H322 H 0.0059 0.0181 0.6417 0.0394 1.0000 Uiso . . H331 H 0.0288 0.1682 0.5450 0.0358 1.0000 Uiso . . H332 H 0.0512 0.0058 0.5469 0.0358 1.0000 Uiso . . H341 H 0.1492 0.2046 0.5954 0.0279 1.0000 Uiso . . H351 H 0.1830 -0.0246 0.6086 0.0288 1.0000 Uiso . . H352 H 0.1585 -0.0610 0.5345 0.0288 1.0000 Uiso . . H381 H 0.4098 -0.0993 0.5538 0.0304 1.0000 Uiso . . H401 H 0.3424 0.2655 0.4675 0.0259 1.0000 Uiso . . H421 H 0.0729 0.1157 0.4385 0.0397 1.0000 Uiso . . H422 H 0.1508 0.0543 0.4362 0.0397 1.0000 Uiso . . H423 H 0.1296 0.1986 0.3998 0.0397 1.0000 Uiso . . H431 H 0.1652 0.6046 0.7281 0.0511 1.0000 Uiso . . H432 H 0.1811 0.4671 0.6870 0.0511 1.0000 Uiso . . H433 H 0.1890 0.6199 0.6558 0.0511 1.0000 Uiso . . H441 H 0.0627 0.7453 0.7009 0.0637 1.0000 Uiso . . H442 H 0.0064 0.7005 0.6430 0.0637 1.0000 Uiso . . H443 H 0.0810 0.7631 0.6270 0.0637 1.0000 Uiso . . H451 H -0.0697 0.3501 0.6524 0.0728 1.0000 Uiso . . H452 H -0.0873 0.1854 0.6519 0.0728 1.0000 Uiso . . H453 H -0.0605 0.2586 0.5885 0.0728 1.0000 Uiso . . H461 H 0.3366 -0.2410 0.6052 0.0347 1.0000 Uiso . . H462 H 0.2771 -0.1601 0.6410 0.0347 1.0000 Uiso . . H463 H 0.2569 -0.2436 0.5748 0.0347 1.0000 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0292(6) 0.0275(6) 0.0292(6) -0.0032(5) 0.0084(5) -0.0089(5) C1 0.0233(8) 0.0299(8) 0.0239(8) -0.0028(7) 0.0014(6) -0.0032(7) C2 0.0242(8) 0.0301(9) 0.0356(9) -0.0081(7) 0.0037(7) -0.0063(7) C3 0.0274(8) 0.0243(8) 0.0317(9) -0.0022(7) 0.0063(7) -0.0073(7) C4 0.0288(8) 0.0276(8) 0.0274(8) -0.0036(7) 0.0033(6) -0.0063(7) C5 0.0316(9) 0.0246(8) 0.0269(8) 0.0001(7) 0.0063(7) -0.0031(7) C6 0.0278(8) 0.0324(9) 0.0391(10) 0.0021(8) 0.0084(7) 0.0007(7) C7 0.0245(8) 0.0305(9) 0.0384(10) 0.0009(8) 0.0081(7) -0.0052(7) C8 0.0354(9) 0.0336(9) 0.0343(9) 0.0031(8) 0.0179(7) -0.0024(8) C9 0.0374(10) 0.0302(9) 0.0351(10) 0.0063(8) 0.0146(8) -0.0047(8) C10 0.0373(9) 0.0291(9) 0.0229(8) 0.0030(7) 0.0045(7) 0.0000(7) C11 0.0239(8) 0.0238(8) 0.0226(8) 0.0004(6) 0.0033(6) -0.0035(6) C12 0.0266(8) 0.0244(8) 0.0258(8) 0.0001(7) 0.0054(6) -0.0046(7) C13 0.0190(7) 0.0223(8) 0.0249(8) 0.0019(6) 0.0031(6) 0.0013(6) C14 0.0199(7) 0.0245(8) 0.0286(8) -0.0012(6) 0.0027(6) 0.0011(6) C15 0.0300(8) 0.0279(8) 0.0249(8) -0.0026(7) 0.0035(7) 0.0063(7) C16 0.0343(9) 0.0243(8) 0.0287(9) 0.0045(7) 0.0146(7) 0.0074(7) C17 0.0258(8) 0.0222(8) 0.0341(9) 0.0060(7) 0.0106(7) 0.0028(7) C18 0.0205(7) 0.0210(7) 0.0278(8) 0.0003(6) 0.0026(6) 0.0031(6) C19 0.0261(9) 0.0438(11) 0.0392(10) -0.0029(9) -0.0028(7) 0.0018(8) C20 0.0485(11) 0.0340(10) 0.0275(9) 0.0008(7) 0.0017(8) 0.0041(8) C21 0.0451(11) 0.0291(9) 0.0356(10) -0.0019(8) 0.0084(8) 0.0019(8) C22 0.0839(17) 0.0488(13) 0.0339(11) 0.0048(10) 0.0213(11) 0.0158(12) C23 0.0312(9) 0.0367(10) 0.0428(11) -0.0148(8) 0.0115(8) -0.0102(8) O2 0.0753(11) 0.0332(8) 0.0446(9) 0.0078(7) 0.0400(8) 0.0120(8) O3 0.0190(5) 0.0251(6) 0.0296(6) 0.0033(5) 0.0031(4) 0.0042(5) C24 0.0175(7) 0.0318(9) 0.0259(8) -0.0001(7) 0.0013(6) 0.0043(6) C25 0.0263(8) 0.0357(9) 0.0287(9) 0.0055(7) 0.0043(6) 0.0106(7) C26 0.0276(8) 0.0253(8) 0.0357(9) 0.0051(7) 0.0047(7) 0.0071(7) C27 0.0314(9) 0.0308(9) 0.0351(10) 0.0027(7) 0.0037(7) 0.0099(7) C28 0.0370(10) 0.0281(9) 0.0382(10) -0.0026(8) 0.0093(8) 0.0054(8) C29 0.0392(10) 0.0384(11) 0.0406(11) -0.0066(8) 0.0144(8) 0.0029(8) C30 0.0339(9) 0.0338(9) 0.0318(9) 0.0004(8) 0.0123(7) 0.0024(8) C31 0.0265(9) 0.0385(10) 0.0448(11) -0.0045(8) 0.0163(8) -0.0014(8) C32 0.0253(8) 0.0322(9) 0.0410(10) -0.0034(8) 0.0120(7) -0.0032(7) C33 0.0194(7) 0.0357(9) 0.0343(9) -0.0048(8) 0.0032(7) 0.0002(7) C34 0.0183(7) 0.0267(8) 0.0249(8) -0.0021(6) 0.0031(6) 0.0007(6) C35 0.0207(7) 0.0249(8) 0.0264(8) -0.0007(6) 0.0038(6) -0.0003(6) C36 0.0212(7) 0.0231(8) 0.0192(7) -0.0026(6) 0.0020(6) 0.0011(6) C37 0.0242(8) 0.0218(7) 0.0220(8) -0.0011(6) 0.0025(6) 0.0021(6) C38 0.0219(8) 0.0262(8) 0.0279(8) 0.0012(7) 0.0027(6) 0.0065(6) C39 0.0174(7) 0.0279(8) 0.0242(8) -0.0038(6) 0.0048(6) -0.0005(6) C40 0.0219(7) 0.0227(7) 0.0201(7) -0.0004(6) 0.0031(6) 0.0005(6) C41 0.0199(7) 0.0230(8) 0.0203(7) -0.0022(6) 0.0001(6) 0.0036(6) C42 0.0264(8) 0.0457(11) 0.0271(9) -0.0039(8) 0.0006(7) 0.0040(8) C43 0.0437(11) 0.0386(11) 0.0455(11) -0.0066(9) 0.0059(9) -0.0046(9) C44 0.0718(16) 0.0333(11) 0.0542(14) -0.0025(10) 0.0191(12) 0.0171(11) C45 0.0266(10) 0.0614(15) 0.094(2) -0.0231(14) 0.0121(11) 0.0046(10) C46 0.0312(9) 0.0256(8) 0.0299(9) 0.0051(7) 0.0067(7) 0.0054(7) O4 0.0194(6) 0.0390(7) 0.0436(8) -0.0026(6) 0.0102(5) -0.0002(5) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4651(19) yes O1 . C18 . 1.365(2) yes C1 . C2 . 1.542(2) yes C1 . C11 . 1.542(2) yes C1 . C19 . 1.524(3) yes C2 . C3 . 1.503(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.323(2) yes C3 . H31 . 1.000 no C4 . C5 . 1.515(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.566(2) yes C5 . C20 . 1.524(2) yes C5 . C21 . 1.532(2) yes C6 . C7 . 1.506(3) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.328(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.515(3) yes C8 . C22 . 1.504(3) yes C9 . C10 . 1.543(3) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C10 . C11 . 1.540(2) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . C12 . 1.528(2) yes C11 . H111 . 1.000 no C12 . C13 . 1.505(2) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . C14 . 1.402(2) yes C13 . C18 . 1.395(2) yes C14 . C15 . 1.389(2) yes C14 . C23 . 1.507(2) yes C15 . C16 . 1.386(3) yes C15 . H151 . 1.000 no C16 . C17 . 1.380(3) yes C16 . O2 . 1.383(2) yes C17 . C18 . 1.398(2) yes C17 . H171 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no O2 . H1 . 0.76(5) yes O2 . H2 . 0.83(4) yes O3 . C24 . 1.4670(19) yes O3 . C41 . 1.3779(19) yes C24 . C25 . 1.543(2) yes C24 . C34 . 1.540(2) yes C24 . C42 . 1.524(2) yes C25 . C26 . 1.506(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.325(2) yes C26 . H261 . 1.000 no C27 . C28 . 1.516(3) yes C27 . H271 . 1.000 no C28 . C29 . 1.565(3) yes C28 . C43 . 1.522(3) yes C28 . C44 . 1.538(3) yes C29 . C30 . 1.506(3) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . C31 . 1.328(3) yes C30 . H301 . 1.000 no C31 . C32 . 1.511(3) yes C31 . C45 . 1.502(3) yes C32 . C33 . 1.549(3) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C33 . C34 . 1.544(2) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no C34 . C35 . 1.529(2) yes C34 . H341 . 1.000 no C35 . C36 . 1.508(2) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no C36 . C37 . 1.401(2) yes C36 . C41 . 1.393(2) yes C37 . C38 . 1.391(2) yes C37 . C46 . 1.511(2) yes C38 . C39 . 1.389(2) yes C38 . H381 . 1.000 no C39 . C40 . 1.384(2) yes C39 . O4 . 1.3830(19) yes C40 . C41 . 1.400(2) yes C40 . H401 . 1.000 no C42 . H421 . 1.000 no C42 . H422 . 1.000 no C42 . H423 . 1.000 no C43 . H431 . 1.000 no C43 . H432 . 1.000 no C43 . H433 . 1.000 no C44 . H441 . 1.000 no C44 . H442 . 1.000 no C44 . H443 . 1.000 no C45 . H451 . 1.000 no C45 . H452 . 1.000 no C45 . H453 . 1.000 no C46 . H461 . 1.000 no C46 . H462 . 1.000 no C46 . H463 . 1.000 no O4 . H3 . 0.83(5) yes O4 . H4 . 0.83(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C18 . 119.91(12) yes O1 . C1 . C2 . 101.34(13) yes O1 . C1 . C11 . 110.32(12) yes C2 . C1 . C11 . 112.17(13) yes O1 . C1 . C19 . 107.47(14) yes C2 . C1 . C19 . 112.02(14) yes C11 . C1 . C19 . 112.81(15) yes C1 . C2 . C3 . 111.71(14) yes C1 . C2 . H21 . 108.910 no C3 . C2 . H21 . 108.909 no C1 . C2 . H22 . 108.909 no C3 . C2 . H22 . 108.909 no H21 . C2 . H22 . 109.467 no C2 . C3 . C4 . 125.06(16) yes C2 . C3 . H31 . 117.471 no C4 . C3 . H31 . 117.471 no C3 . C4 . C5 . 127.20(16) yes C3 . C4 . H41 . 116.398 no C5 . C4 . H41 . 116.398 no C4 . C5 . C6 . 106.16(14) yes C4 . C5 . C20 . 112.59(14) yes C6 . C5 . C20 . 109.05(15) yes C4 . C5 . C21 . 110.84(15) yes C6 . C5 . C21 . 108.28(14) yes C20 . C5 . C21 . 109.76(15) yes C5 . C6 . C7 . 111.57(14) yes C5 . C6 . H61 . 108.945 no C7 . C6 . H61 . 108.945 no C5 . C6 . H62 . 108.944 no C7 . C6 . H62 . 108.945 no H61 . C6 . H62 . 109.466 no C6 . C7 . C8 . 125.94(18) yes C6 . C7 . H71 . 117.029 no C8 . C7 . H71 . 117.029 no C7 . C8 . C9 . 121.45(17) yes C7 . C8 . C22 . 124.56(18) yes C9 . C8 . C22 . 113.87(17) yes C8 . C9 . C10 . 110.97(15) yes C8 . C9 . H91 . 109.096 no C10 . C9 . H91 . 109.097 no C8 . C9 . H92 . 109.096 no C10 . C9 . H92 . 109.097 no H91 . C9 . H92 . 109.467 no C9 . C10 . C11 . 113.35(14) yes C9 . C10 . H101 . 108.494 no C11 . C10 . H101 . 108.494 no C9 . C10 . H102 . 108.494 no C11 . C10 . H102 . 108.494 no H101 . C10 . H102 . 109.467 no C1 . C11 . C10 . 112.90(13) yes C1 . C11 . C12 . 111.28(13) yes C10 . C11 . C12 . 110.32(13) yes C1 . C11 . H111 . 106.081 no C10 . C11 . H111 . 107.119 no C12 . C11 . H111 . 108.891 no C11 . C12 . C13 . 112.86(13) yes C11 . C12 . H121 . 108.619 no C13 . C12 . H121 . 108.619 no C11 . C12 . H122 . 108.619 no C13 . C12 . H122 . 108.619 no H121 . C12 . H122 . 109.467 no C12 . C13 . C14 . 122.12(14) yes C12 . C13 . C18 . 119.44(14) yes C14 . C13 . C18 . 118.41(14) yes C13 . C14 . C15 . 120.47(15) yes C13 . C14 . C23 . 119.90(15) yes C15 . C14 . C23 . 119.61(15) yes C14 . C15 . C16 . 119.66(15) yes C14 . C15 . H151 . 120.167 no C16 . C15 . H151 . 120.168 no C15 . C16 . C17 . 121.37(15) yes C15 . C16 . O2 . 118.75(16) yes C17 . C16 . O2 . 119.88(16) yes C16 . C17 . C18 . 118.58(15) yes C16 . C17 . H171 . 120.711 no C18 . C17 . H171 . 120.710 no O1 . C18 . C13 . 123.38(14) yes O1 . C18 . C17 . 115.15(14) yes C13 . C18 . C17 . 121.45(15) yes C1 . C19 . H191 . 109.467 no C1 . C19 . H192 . 109.466 no H191 . C19 . H192 . 109.476 no C1 . C19 . H193 . 109.466 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no C5 . C20 . H201 . 109.467 no C5 . C20 . H202 . 109.467 no H201 . C20 . H202 . 109.476 no C5 . C20 . H203 . 109.467 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.476 no C5 . C21 . H211 . 109.467 no C5 . C21 . H212 . 109.467 no H211 . C21 . H212 . 109.476 no C5 . C21 . H213 . 109.466 no H211 . C21 . H213 . 109.475 no H212 . C21 . H213 . 109.476 no C8 . C22 . H221 . 109.467 no C8 . C22 . H222 . 109.467 no H221 . C22 . H222 . 109.476 no C8 . C22 . H223 . 109.467 no H221 . C22 . H223 . 109.476 no H222 . C22 . H223 . 109.476 no C14 . C23 . H231 . 109.466 no C14 . C23 . H232 . 109.467 no H231 . C23 . H232 . 109.475 no C14 . C23 . H233 . 109.467 no H231 . C23 . H233 . 109.476 no H232 . C23 . H233 . 109.476 no C16 . O2 . H1 . 116(4) yes C16 . O2 . H2 . 111(3) yes C24 . O3 . C41 . 118.49(12) yes O3 . C24 . C25 . 102.41(13) yes O3 . C24 . C34 . 109.47(12) yes C25 . C24 . C34 . 112.80(13) yes O3 . C24 . C42 . 108.22(13) yes C25 . C24 . C42 . 110.32(14) yes C34 . C24 . C42 . 113.01(15) yes C24 . C25 . C26 . 113.73(14) yes C24 . C25 . H251 . 108.398 no C26 . C25 . H251 . 108.398 no C24 . C25 . H252 . 108.398 no C26 . C25 . H252 . 108.398 no H251 . C25 . H252 . 109.467 no C25 . C26 . C27 . 124.34(17) yes C25 . C26 . H261 . 117.831 no C27 . C26 . H261 . 117.830 no C26 . C27 . C28 . 128.14(17) yes C26 . C27 . H271 . 115.931 no C28 . C27 . H271 . 115.932 no C27 . C28 . C29 . 106.89(16) yes C27 . C28 . C43 . 112.60(15) yes C29 . C28 . C43 . 109.43(17) yes C27 . C28 . C44 . 109.67(17) yes C29 . C28 . C44 . 108.64(16) yes C43 . C28 . C44 . 109.52(18) yes C28 . C29 . C30 . 111.45(15) yes C28 . C29 . H291 . 108.974 no C30 . C29 . H291 . 108.975 no C28 . C29 . H292 . 108.974 no C30 . C29 . H292 . 108.975 no H291 . C29 . H292 . 109.467 no C29 . C30 . C31 . 126.40(18) yes C29 . C30 . H301 . 116.800 no C31 . C30 . H301 . 116.800 no C30 . C31 . C32 . 121.65(17) yes C30 . C31 . C45 . 124.45(19) yes C32 . C31 . C45 . 113.68(18) yes C31 . C32 . C33 . 110.22(16) yes C31 . C32 . H321 . 109.284 no C33 . C32 . H321 . 109.284 no C31 . C32 . H322 . 109.284 no C33 . C32 . H322 . 109.284 no H321 . C32 . H322 . 109.467 no C32 . C33 . C34 . 113.17(14) yes C32 . C33 . H331 . 108.539 no C34 . C33 . H331 . 108.539 no C32 . C33 . H332 . 108.539 no C34 . C33 . H332 . 108.539 no H331 . C33 . H332 . 109.467 no C24 . C34 . C33 . 114.05(13) yes C24 . C34 . C35 . 110.60(13) yes C33 . C34 . C35 . 109.12(14) yes C24 . C34 . H341 . 105.349 no C33 . C34 . H341 . 106.941 no C35 . C34 . H341 . 110.657 no C34 . C35 . C36 . 113.21(13) yes C34 . C35 . H351 . 108.531 no C36 . C35 . H351 . 108.531 no C34 . C35 . H352 . 108.530 no C36 . C35 . H352 . 108.530 no H351 . C35 . H352 . 109.466 no C35 . C36 . C37 . 121.63(14) yes C35 . C36 . C41 . 119.82(14) yes C37 . C36 . C41 . 118.54(14) yes C36 . C37 . C38 . 120.21(15) yes C36 . C37 . C46 . 120.46(14) yes C38 . C37 . C46 . 119.33(14) yes C37 . C38 . C39 . 120.12(14) yes C37 . C38 . H381 . 119.940 no C39 . C38 . H381 . 119.940 no C38 . C39 . C40 . 120.92(14) yes C38 . C39 . O4 . 118.99(15) yes C40 . C39 . O4 . 120.09(15) yes C39 . C40 . C41 . 118.52(14) yes C39 . C40 . H401 . 120.741 no C41 . C40 . H401 . 120.741 no O3 . C41 . C36 . 122.88(13) yes O3 . C41 . C40 . 115.40(14) yes C36 . C41 . C40 . 121.69(14) yes C24 . C42 . H421 . 109.467 no C24 . C42 . H422 . 109.467 no H421 . C42 . H422 . 109.476 no C24 . C42 . H423 . 109.467 no H421 . C42 . H423 . 109.475 no H422 . C42 . H423 . 109.476 no C28 . C43 . H431 . 109.467 no C28 . C43 . H432 . 109.467 no H431 . C43 . H432 . 109.476 no C28 . C43 . H433 . 109.466 no H431 . C43 . H433 . 109.475 no H432 . C43 . H433 . 109.476 no C28 . C44 . H441 . 109.466 no C28 . C44 . H442 . 109.467 no H441 . C44 . H442 . 109.476 no C28 . C44 . H443 . 109.467 no H441 . C44 . H443 . 109.475 no H442 . C44 . H443 . 109.476 no C31 . C45 . H451 . 109.466 no C31 . C45 . H452 . 109.466 no H451 . C45 . H452 . 109.476 no C31 . C45 . H453 . 109.467 no H451 . C45 . H453 . 109.476 no H452 . C45 . H453 . 109.476 no C37 . C46 . H461 . 109.467 no C37 . C46 . H462 . 109.467 no H461 . C46 . H462 . 109.475 no C37 . C46 . H463 . 109.467 no H461 . C46 . H463 . 109.476 no H462 . C46 . H463 . 109.476 no C39 . O4 . H3 . 117(3) yes C39 . O4 . H4 . 124(3) yes loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _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 O2 H1 O4 . 0.76(5) 2.02(5) 2.779(2) 177(5) yes O2 H2 O2 2_666 0.83(4) 2.00(4) 2.818(3) 167(5) yes O4 H3 O2 . 0.83(5) 1.97(5) 2.779(2) 165(5) yes O4 H4 O4 2_656 0.83(4) 2.04(4) 2.863(3) 171(5) yes data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 239364' _audit_creation_date 04-18-05 _audit_creation_method CRYSTALS_ver_12-03-99 # arc831 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_name_common alboatrin _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The OH hydrogen atom was loacted in a difference Fourier map and its coordinates and isotropic thermal parameter subsequently refined. Other H atoms were positioned geometrically, the preferred orientations of the methyl groups having been determined by examination of the Fourier map. ; #============================================================= _cell_length_a 8.8435(3) _cell_angle_alpha 90 _cell_length_b 13.4040(5) _cell_angle_beta 105.5713(18) _cell_length_c 10.6982(3) _cell_angle_gamma 90 _cell_volume 1221.60(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C14 H18 O3 ' _chemical_formula_moiety ' C14 H18 O3 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 234.30 _cell_measurement_reflns_used 7866 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.34 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.088 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 7866 _reflns_number_total 2767 #2890 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_min 5.153 _diffrn_reflns_theta_max 27.473 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.473 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.20 _refine_diff_density_max 0.23 _refine_ls_number_reflns 1990 _refine_ls_number_restraints 0 _refine_ls_number_parameters 158 #_refine_ls_R_factor_ref 0.0378 _refine_ls_wR_factor_ref 0.0498 _refine_ls_goodness_of_fit_ref 1.0860 #_reflns_number_all 2767 _refine_ls_R_factor_all 0.0569 _refine_ls_wR_factor_all 0.0544 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1990 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_gt 0.0498 _refine_ls_shift/su_max 0.003708 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.35 0.672 1.02 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 O 0.43413(11) 0.17033(7) 0.35240(9) 0.0261 1.0000 Uani C1 C 0.43330(16) 0.22445(11) 0.47006(12) 0.0287 1.0000 Uani C2 C 0.39357(15) 0.33343(10) 0.43127(12) 0.0267 1.0000 Uani C3 C 0.33841(13) 0.32727(9) 0.28228(12) 0.0218 1.0000 Uani C4 C 0.35703(14) 0.42254(10) 0.20996(12) 0.0236 1.0000 Uani C5 C 0.52428(13) 0.43840(9) 0.20550(11) 0.0195 1.0000 Uani C6 C 0.57529(14) 0.53007(9) 0.16695(11) 0.0195 1.0000 Uani C7 C 0.72955(14) 0.54254(9) 0.16215(11) 0.0206 1.0000 Uani C8 C 0.83633(14) 0.46425(9) 0.19584(12) 0.0212 1.0000 Uani C9 C 0.78943(14) 0.37344(9) 0.23486(12) 0.0222 1.0000 Uani C10 C 0.63405(14) 0.36159(9) 0.23826(11) 0.0208 1.0000 Uani O2 O 0.59863(10) 0.26890(7) 0.27871(10) 0.0286 1.0000 Uani C11 C 0.43537(14) 0.24084(9) 0.25481(12) 0.0233 1.0000 Uani C12 C 0.2727(2) 0.37865(14) 0.49253(16) 0.0422 1.0000 Uani C13 C 0.46090(15) 0.61535(9) 0.13028(12) 0.0241 1.0000 Uani O3 O 0.98888(11) 0.47240(8) 0.19004(10) 0.0294 1.0000 Uani C14 C 0.38103(18) 0.19154(11) 0.12351(14) 0.0333 1.0000 Uani H1 H 1.006(3) 0.5336(18) 0.170(2) 0.051(6) 1.0000 Uiso H11 H 0.5389 0.2202 0.5340 0.0341 1.0000 Uiso H12 H 0.3523 0.1957 0.5094 0.0341 1.0000 Uiso H21 H 0.4846 0.3796 0.4631 0.0319 1.0000 Uiso H31 H 0.2223 0.3174 0.2499 0.0267 1.0000 Uiso H41 H 0.3238 0.4807 0.2549 0.0289 1.0000 Uiso H42 H 0.2883 0.4181 0.1191 0.0289 1.0000 Uiso H71 H 0.7641 0.6080 0.1344 0.0249 1.0000 Uiso H91 H 0.8660 0.3173 0.2602 0.0271 1.0000 Uiso H121 H 0.2522 0.4494 0.4634 0.0519 1.0000 Uiso H122 H 0.3136 0.3766 0.5892 0.0519 1.0000 Uiso H123 H 0.1729 0.3396 0.4653 0.0519 1.0000 Uiso H131 H 0.5154 0.6745 0.1055 0.0291 1.0000 Uiso H132 H 0.4197 0.6329 0.2058 0.0291 1.0000 Uiso H133 H 0.3718 0.5952 0.0552 0.0291 1.0000 Uiso H141 H 0.3818 0.2414 0.0542 0.0412 1.0000 Uiso H142 H 0.4532 0.1352 0.1184 0.0412 1.0000 Uiso H143 H 0.2721 0.1654 0.1109 0.0412 1.0000 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0288(4) 0.0217(4) 0.0306(5) 0.0063(4) 0.0132(4) 0.0006(4) C1 0.0298(7) 0.0316(7) 0.0239(6) 0.0045(5) 0.0057(5) -0.0037(5) C2 0.0259(6) 0.0280(7) 0.0259(6) -0.0004(5) 0.0067(5) -0.0008(5) C3 0.0180(5) 0.0237(6) 0.0251(6) 0.0009(5) 0.0082(4) -0.0005(4) C4 0.0187(5) 0.0233(6) 0.0302(6) 0.0043(5) 0.0090(4) 0.0023(5) C5 0.0191(5) 0.0194(6) 0.0216(6) 0.0005(4) 0.0081(4) 0.0019(4) C6 0.0213(6) 0.0180(5) 0.0192(5) -0.0013(4) 0.0057(4) 0.0013(4) C7 0.0226(6) 0.0185(6) 0.0212(5) -0.0018(4) 0.0068(4) -0.0016(4) C8 0.0175(5) 0.0239(6) 0.0230(5) -0.0029(5) 0.0069(4) -0.0015(4) C9 0.0198(5) 0.0217(6) 0.0262(6) 0.0013(5) 0.0081(4) 0.0037(4) C10 0.0219(6) 0.0186(6) 0.0239(6) 0.0032(5) 0.0093(4) 0.0013(4) O2 0.0214(4) 0.0220(4) 0.0456(6) 0.0121(4) 0.0146(4) 0.0039(3) C11 0.0221(6) 0.0216(6) 0.0285(6) 0.0055(5) 0.0110(5) 0.0005(5) C12 0.0460(9) 0.0515(10) 0.0323(7) -0.0061(7) 0.0159(7) 0.0063(7) C13 0.0255(6) 0.0183(5) 0.0288(6) 0.0015(5) 0.0077(5) 0.0026(5) O3 0.0194(4) 0.0252(5) 0.0461(6) 0.0010(4) 0.0133(4) -0.0015(4) C14 0.0397(7) 0.0307(7) 0.0325(7) -0.0005(6) 0.0148(6) 0.0026(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4546(16) yes O1 . C11 . 1.4104(15) yes C1 . C2 . 1.5333(19) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C2 . C3 . 1.5389(18) yes C2 . C12 . 1.522(2) yes C2 . H21 . 1.000 no C3 . C4 . 1.5247(17) yes C3 . C11 . 1.5163(17) yes C3 . H31 . 1.000 no C4 . C5 . 1.5077(16) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.4082(16) yes C5 . C10 . 1.3937(16) yes C6 . C7 . 1.3890(17) yes C6 . C13 . 1.5070(16) yes C7 . C8 . 1.3929(17) yes C7 . H71 . 1.000 no C8 . C9 . 1.3860(17) yes C8 . O3 . 1.3714(14) yes C9 . C10 . 1.3934(16) yes C9 . H91 . 1.000 no C10 . O2 . 1.3791(14) yes O2 . C11 . 1.4468(15) yes C11 . C14 . 1.5094(19) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no O3 . H1 . 0.87(2) no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C11 . 108.01(10) yes O1 . C1 . C2 . 107.16(10) yes O1 . C1 . H11 . 110.048 no C2 . C1 . H11 . 110.048 no O1 . C1 . H12 . 110.048 no C2 . C1 . H12 . 110.048 no H11 . C1 . H12 . 109.467 no C1 . C2 . C3 . 102.42(10) yes C1 . C2 . C12 . 113.54(12) yes C3 . C2 . C12 . 113.79(11) yes C1 . C2 . H21 . 113.117 no C3 . C2 . H21 . 112.861 no C12 . C2 . H21 . 101.581 no C2 . C3 . C4 . 115.68(10) yes C2 . C3 . C11 . 101.73(10) yes C4 . C3 . C11 . 113.45(10) yes C2 . C3 . H31 . 112.126 no C4 . C3 . H31 . 100.076 no C11 . C3 . H31 . 114.417 no C3 . C4 . C5 . 112.00(9) yes C3 . C4 . H41 . 108.836 no C5 . C4 . H41 . 108.836 no C3 . C4 . H42 . 108.836 no C5 . C4 . H42 . 108.836 no H41 . C4 . H42 . 109.467 no C4 . C5 . C6 . 121.76(10) yes C4 . C5 . C10 . 120.72(11) yes C6 . C5 . C10 . 117.51(10) yes C5 . C6 . C7 . 120.72(11) yes C5 . C6 . C13 . 119.52(10) yes C7 . C6 . C13 . 119.76(11) yes C6 . C7 . C8 . 120.27(11) yes C6 . C7 . H71 . 119.862 no C8 . C7 . H71 . 119.863 no C7 . C8 . C9 . 120.18(11) yes C7 . C8 . O3 . 122.35(11) yes C9 . C8 . O3 . 117.46(11) yes C8 . C9 . C10 . 119.01(11) yes C8 . C9 . H91 . 120.497 no C10 . C9 . H91 . 120.496 no C5 . C10 . C9 . 122.31(11) yes C5 . C10 . O2 . 122.88(10) yes C9 . C10 . O2 . 114.80(10) yes C10 . O2 . C11 . 118.60(9) yes O1 . C11 . C3 . 104.56(10) yes O1 . C11 . O2 . 104.42(10) yes C3 . C11 . O2 . 110.89(10) yes O1 . C11 . C14 . 109.38(11) yes C3 . C11 . C14 . 117.36(11) yes O2 . C11 . C14 . 109.37(10) yes C2 . C12 . H121 . 109.467 no C2 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no C2 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C6 . C13 . H131 . 109.467 no C6 . C13 . H132 . 109.467 no H131 . C13 . H132 . 109.476 no C6 . C13 . H133 . 109.467 no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C8 . O3 . H1 . 109.0(15) no C11 . C14 . H141 . 109.467 no C11 . C14 . H142 . 109.467 no H141 . C14 . H142 . 109.476 no C11 . C14 . H143 . 109.467 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _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 O3 H1 O1 3_655 0.87(2) 1.94(2) 2.8062(14) 173(2) yes