# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1343 data_1 loop_ _publ_contact_author_name _publ_contact_author_address 'Prof. Judith A.K. Howard' ; Chemistry Department University of Durham South Road Durham DH1 3LE UK ; 'Prof. Gautam R. Desiraju' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; loop_ _publ_author_name _publ_author_address 'Howard, Judith A.K.' ; Chemistry Department University of Durham South Road Durham DH1 3LE UK ; 'Bilton, Clair' ; Chemistry Department University of Durham South Road Durham DH1 3LE UK ; 'Desiraju, Gautam R.' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; 'Madhavi, N.N. Laxmi' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; 'Nangia, Ashwini' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; 'Allen, Frank H.' ;Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1EZ UK ; 'Wilson, Chick C.' ;ISIS Department CLRC Rutherford Appleton Laboratory Chilton Didcot Oxon OX11 0QX UK ; _publ_requested_journal 'ChemComm' _publ_section_title ; When is a polymorph not a polymorph? Helical trimeric O-H...O synthons in trans-1,4-diethynyl-1,4-cyclohexanediol. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H12 O2' _chemical_formula_sum 'C10 H12 O2' _chemical_formula_weight 164.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2074(3) _cell_length_b 10.0187(5) _cell_length_c 11.5666(5) _cell_angle_alpha 103.005(2) _cell_angle_beta 93.424(2) _cell_angle_gamma 94.572(2) _cell_volume 696.41(6) _cell_formula_units_Z 3 _cell_measurement_temperature 150 _cell_measurement_reflns_used 999 _cell_measurement_theta_min 10.26 _cell_measurement_theta_max 30.69 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.284 _exptl_absorpt_correction_T_max 0.332 _exptl_absorpt_process_details 'empirical using psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5564 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 30.33 _reflns_number_total 3618 _reflns_number_gt 3027 _reflns_threshold_expression 2sigma(I) _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 30.33 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.216 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.050 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.1318P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3618 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.34099(13) 0.14331(9) 0.66737(7) 0.02972(19) Uani 1 1 d . . . H1A H -0.425(3) 0.1881(17) 0.7153(15) 0.045(4) Uiso 1 1 d . . . H1 H -0.270(4) 0.488(2) 0.4972(19) 0.074(6) Uiso 1 1 d . . . C1 C -0.3042(3) 0.39705(16) 0.51173(14) 0.0457(3) Uani 1 1 d . . . C2 C -0.35463(19) 0.28609(13) 0.52808(11) 0.0328(3) Uani 1 1 d . . . C3 C -0.41074(17) 0.14627(11) 0.54678(9) 0.0255(2) Uani 1 1 d . . . C4 C -0.65652(17) 0.10455(12) 0.52329(10) 0.0261(2) Uani 1 1 d . . . H4A H -0.735(2) 0.1692(15) 0.5820(13) 0.036(4) Uiso 1 1 d . . . H4B H -0.697(2) 0.1126(14) 0.4429(13) 0.028(3) Uiso 1 1 d . . . C5 C -0.71334(18) -0.04250(12) 0.53606(10) 0.0272(2) Uani 1 1 d . . . H5A H -0.870(3) -0.0737(16) 0.5183(14) 0.038(4) Uiso 1 1 d . . . H5B H -0.678(2) -0.0499(14) 0.6181(13) 0.029(3) Uiso 1 1 d . . . O2 O 0.38323(14) 0.26651(8) 0.81728(7) 0.03075(19) Uani 1 1 d . . . H2A H 0.250(3) 0.2235(17) 0.8136(15) 0.046(4) Uiso 1 1 d . . . H11 H 0.089(3) 0.623(2) 0.7444(18) 0.068(6) Uiso 1 1 d . . . C11 C 0.1733(2) 0.56502(16) 0.78017(13) 0.0440(3) Uani 1 1 d . . . C12 C 0.27363(19) 0.49228(12) 0.82643(10) 0.0304(2) Uani 1 1 d . . . C13 C 0.39881(16) 0.40439(11) 0.88804(9) 0.0238(2) Uani 1 1 d . . . C14 C 0.64147(17) 0.45466(11) 0.90316(10) 0.0247(2) Uani 1 1 d . . . H14A H 0.694(2) 0.4572(15) 0.8264(13) 0.034(4) Uiso 1 1 d . . . H14B H 0.717(2) 0.3843(15) 0.9350(12) 0.031(3) Uiso 1 1 d . . . C15 C 0.68656(17) 0.59534(11) 0.98982(9) 0.0248(2) Uani 1 1 d . . . H15A H 0.611(2) 0.6675(15) 0.9569(13) 0.031(3) Uiso 1 1 d . . . H15B H 0.845(3) 0.6221(15) 1.0009(13) 0.039(4) Uiso 1 1 d . . . O3 O 0.01627(13) 0.09703(8) 0.79038(7) 0.02692(18) Uani 1 1 d . . . H3A H -0.100(3) 0.1066(18) 0.7492(16) 0.054(5) Uiso 1 1 d . . . H21 H -0.383(3) -0.293(2) 0.7199(18) 0.065(5) Uiso 1 1 d . . . C21 C -0.2870(2) -0.21280(13) 0.76288(11) 0.0350(3) Uani 1 1 d . . . C22 C -0.17092(17) -0.11307(11) 0.81121(9) 0.0260(2) Uani 1 1 d . . . C23 C -0.03472(16) 0.01416(10) 0.87363(9) 0.0221(2) Uani 1 1 d . . . C24 C -0.15573(16) 0.09509(11) 0.97517(9) 0.0232(2) Uani 1 1 d . . . H24A H -0.299(2) 0.1122(14) 0.9425(12) 0.031(3) Uiso 1 1 d . . . H24B H -0.070(2) 0.1857(14) 1.0077(12) 0.028(3) Uiso 1 1 d . . . C25 C -0.18398(16) 0.01978(11) 1.07556(9) 0.0234(2) Uani 1 1 d . . . H25A H -0.260(2) 0.0728(14) 1.1406(12) 0.031(3) Uiso 1 1 d . . . H25B H -0.274(2) -0.0702(14) 1.0466(12) 0.028(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0294(4) 0.0391(4) 0.0204(4) 0.0045(3) -0.0026(3) 0.0120(3) C1 0.0476(8) 0.0389(7) 0.0522(8) 0.0140(6) 0.0029(6) 0.0044(6) C2 0.0305(6) 0.0358(6) 0.0321(6) 0.0072(5) -0.0002(4) 0.0074(5) C3 0.0245(5) 0.0318(5) 0.0209(5) 0.0065(4) -0.0013(4) 0.0076(4) C4 0.0244(5) 0.0326(5) 0.0218(5) 0.0052(4) 0.0000(4) 0.0104(4) C5 0.0229(5) 0.0355(6) 0.0240(5) 0.0066(4) 0.0030(4) 0.0081(4) O2 0.0289(4) 0.0261(4) 0.0320(4) -0.0028(3) 0.0072(3) -0.0054(3) C11 0.0420(7) 0.0528(8) 0.0408(7) 0.0182(6) -0.0008(6) 0.0079(6) C12 0.0293(5) 0.0339(6) 0.0270(5) 0.0063(4) 0.0030(4) -0.0017(4) C13 0.0241(5) 0.0228(5) 0.0228(5) 0.0026(4) 0.0038(4) -0.0021(4) C14 0.0234(5) 0.0244(5) 0.0251(5) 0.0035(4) 0.0056(4) -0.0017(4) C15 0.0245(5) 0.0242(5) 0.0250(5) 0.0052(4) 0.0056(4) -0.0035(4) O3 0.0237(4) 0.0329(4) 0.0276(4) 0.0174(3) -0.0025(3) -0.0029(3) C21 0.0390(6) 0.0342(6) 0.0299(6) 0.0096(5) -0.0058(5) -0.0079(5) C22 0.0258(5) 0.0299(5) 0.0236(5) 0.0106(4) -0.0013(4) 0.0002(4) C23 0.0202(4) 0.0249(5) 0.0228(5) 0.0108(4) -0.0016(4) -0.0013(4) C24 0.0205(4) 0.0246(5) 0.0260(5) 0.0096(4) -0.0016(4) 0.0027(4) C25 0.0190(4) 0.0277(5) 0.0251(5) 0.0098(4) 0.0004(4) 0.0017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4430(12) . yes O1 H1A 0.862(18) . yes C1 C2 1.190(2) . yes C1 H1 0.97(2) . yes C2 C3 1.4826(17) . yes C3 C5 1.5361(15) 2_456 yes C3 C4 1.5408(15) . yes C4 C5 1.5291(16) . yes C4 H4A 1.005(15) . yes C4 H4B 0.972(14) . yes C5 C3 1.5361(15) 2_456 yes C5 H5A 0.995(16) . yes C5 H5B 0.981(14) . yes O2 C13 1.4311(12) . yes O2 H2A 0.895(18) . yes C11 C12 1.1889(19) . yes C11 H11 0.96(2) . yes C12 C13 1.4874(16) . yes C13 C14 1.5366(14) . yes C13 C15 1.5377(14) 2_667 yes C14 C15 1.5288(15) . yes C14 H14A 0.970(15) . yes C14 H14B 1.002(14) . yes C15 C13 1.5377(14) 2_667 yes C15 H15A 1.022(15) . yes C15 H15B 0.992(16) . yes O3 C23 1.4391(12) . yes O3 H3A 0.86(2) . yes C21 C22 1.1898(16) . yes C21 H21 0.98(2) . yes C22 C23 1.4839(15) . yes C23 C25 1.5401(14) 2_557 yes C23 C24 1.5410(15) . yes C24 C25 1.5316(14) . yes C24 H24A 0.990(14) . yes C24 H24B 0.998(14) . yes C25 C23 1.5401(14) 2_557 yes C25 H25A 0.988(14) . yes C25 H25B 1.000(14) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1A 109.2(11) . . yes C2 C1 H1 177.3(13) . . yes C1 C2 C3 178.09(13) . . yes O1 C3 C2 109.23(9) . . yes O1 C3 C5 107.15(8) . 2_456 yes C2 C3 C5 109.41(9) . 2_456 yes O1 C3 C4 109.79(9) . . yes C2 C3 C4 111.17(9) . . yes C5 C3 C4 110.00(9) 2_456 . yes C5 C4 C3 111.26(9) . . yes C5 C4 H4A 108.9(9) . . yes C3 C4 H4A 109.2(9) . . yes C5 C4 H4B 110.6(8) . . yes C3 C4 H4B 107.0(8) . . yes H4A C4 H4B 109.9(12) . . yes C4 C5 C3 111.73(9) . 2_456 yes C4 C5 H5A 113.1(9) . . yes C3 C5 H5A 107.3(9) 2_456 . yes C4 C5 H5B 110.7(8) . . yes C3 C5 H5B 108.1(8) 2_456 . yes H5A C5 H5B 105.6(12) . . yes C13 O2 H2A 112.2(11) . . yes C12 C11 H11 178.3(13) . . yes C11 C12 C13 178.16(13) . . yes O2 C13 C12 110.29(9) . . yes O2 C13 C14 105.64(8) . . yes C12 C13 C14 110.70(9) . . yes O2 C13 C15 109.79(8) . 2_667 yes C12 C13 C15 110.25(9) . 2_667 yes C14 C13 C15 110.07(8) . 2_667 yes C15 C14 C13 111.58(8) . . yes C15 C14 H14A 110.9(9) . . yes C13 C14 H14A 110.0(9) . . yes C15 C14 H14B 109.9(8) . . yes C13 C14 H14B 106.3(8) . . yes H14A C14 H14B 107.9(12) . . yes C14 C15 C13 112.26(8) . 2_667 yes C14 C15 H15A 110.0(8) . . yes C13 C15 H15A 106.9(8) 2_667 . yes C14 C15 H15B 109.4(9) . . yes C13 C15 H15B 108.9(9) 2_667 . yes H15A C15 H15B 109.3(12) . . yes C23 O3 H3A 110.4(12) . . yes C22 C21 H21 177.3(12) . . yes C21 C22 C23 177.46(13) . . yes O3 C23 C22 109.67(8) . . yes O3 C23 C25 106.14(8) . 2_557 yes C22 C23 C25 111.08(9) . 2_557 yes O3 C23 C24 110.46(8) . . yes C22 C23 C24 109.74(8) . . yes C25 C23 C24 109.69(8) 2_557 . yes C25 C24 C23 112.46(8) . . yes C25 C24 H24A 109.8(8) . . yes C23 C24 H24A 109.2(8) . . yes C25 C24 H24B 109.2(8) . . yes C23 C24 H24B 107.7(8) . . yes H24A C24 H24B 108.3(11) . . yes C24 C25 C23 111.86(8) . 2_557 yes C24 C25 H25A 111.9(8) . . yes C23 C25 H25A 109.6(8) 2_557 . yes C24 C25 H25B 111.4(8) . . yes C23 C25 H25B 106.1(8) 2_557 . yes H25A C25 H25B 105.7(11) . . yes #===END data_2 _publ_contact_author_name ? _publ_contact_author_address ? _publ_requested_journal ? _publ_section_title ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H12 O2' _chemical_formula_sum 'C10 H12 O2' _chemical_formula_weight 164.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0..0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4140(2) _cell_length_b 9.6367(3) _cell_length_c 11.7852(4) _cell_angle_alpha 105.689(2) _cell_angle_beta 101.838(1) _cell_angle_gamma 94.736(1) _cell_volume 678.98(4) _cell_formula_units_Z 3 _cell_measurement_temperature 150 _cell_measurement_reflns_used 510 _cell_measurement_theta_min 5.12 _cell_measurement_theta_max 28.04 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 4754 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3061 _reflns_number_gt 2554 _reflns_threshold_expression 2sigma(I) _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+0.4113P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3061 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.240 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.049 _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.12386(19) 0.68578(12) 0.67689(11) 0.0222(3) Uani 1 1 d . . . HA H 1.047(4) 0.734(2) 0.721(2) 0.037(6) Uiso 1 1 d . . . C1 C 0.9697(3) 0.4381(2) 0.81993(18) 0.0353(4) Uani 1 1 d . . . H1 H 0.940(4) 0.404(3) 0.885(3) 0.068(8) Uiso 1 1 d . . . C2 C 0.9983(3) 0.48304(17) 0.73940(15) 0.0241(3) Uani 1 1 d . . . C3 C 1.0257(2) 0.53514(16) 0.63476(14) 0.0190(3) Uani 1 1 d . . . C4 C 1.1787(3) 0.44656(17) 0.56924(15) 0.0209(3) Uani 1 1 d . . . C5 C 1.1962(2) 0.48260(17) 0.45247(14) 0.0197(3) Uani 1 1 d . . . O2 O 0.87712(19) 0.84379(12) 0.81177(10) 0.0214(3) Uani 1 1 d . . . HB H 0.751(4) 0.835(2) 0.762(2) 0.043(6) Uiso 1 1 d . . . C11 C 0.5431(3) 0.6511(2) 0.92444(18) 0.0355(4) Uani 1 1 d . . . H11 H 0.430(4) 0.574(3) 0.916(2) 0.064(8) Uiso 1 1 d . . . C12 C 0.6809(3) 0.74489(18) 0.93037(15) 0.0239(3) Uani 1 1 d . . . C13 C 0.8453(2) 0.86397(17) 0.93266(13) 0.0182(3) Uani 1 1 d . . . C14 C 0.7688(2) 1.01199(17) 0.97783(14) 0.0198(3) Uani 1 1 d . . . C15 C 0.9362(3) 1.13946(17) 0.98617(14) 0.0201(3) Uani 1 1 d . . . O3 O 0.49787(19) 0.82035(12) 0.65189(10) 0.0213(3) Uani 1 1 d . . . HC H 0.378(4) 0.782(3) 0.661(2) 0.050(7) Uiso 1 1 d . . . C21 C 0.3243(4) 1.1533(2) 0.7464(2) 0.0432(5) Uani 1 1 d . . . H21 H 0.277(5) 1.233(3) 0.795(3) 0.074(9) Uiso 1 1 d . . . C22 C 0.3903(3) 1.05744(19) 0.68329(15) 0.0267(4) Uani 1 1 d . . . C23 C 0.4707(2) 0.93995(16) 0.60130(14) 0.0187(3) Uani 1 1 d . . . C24 C 0.3142(3) 0.88773(17) 0.47544(15) 0.0211(3) Uani 1 1 d . . . C25 C 0.6951(2) 0.99377(18) 0.58873(15) 0.0212(3) Uani 1 1 d . . . H14B H 0.634(3) 1.0140(19) 0.9218(17) 0.021(4) Uiso 1 1 d . . . H5B H 1.264(3) 0.584(2) 0.4729(17) 0.024(5) Uiso 1 1 d . . . H15B H 0.959(3) 1.133(2) 0.9030(18) 0.027(5) Uiso 1 1 d . . . H5A H 1.286(3) 0.4169(18) 0.4094(16) 0.017(4) Uiso 1 1 d . . . H4A H 1.124(3) 0.3390(19) 0.5508(16) 0.019(4) Uiso 1 1 d . . . H4B H 1.322(3) 0.466(2) 0.6253(18) 0.027(5) Uiso 1 1 d . . . H25B H 0.796(3) 1.033(2) 0.6708(18) 0.025(5) Uiso 1 1 d . . . H15A H 0.886(3) 1.236(2) 1.0198(17) 0.023(5) Uiso 1 1 d . . . H24B H 0.367(3) 0.799(2) 0.4267(18) 0.031(5) Uiso 1 1 d . . . H24A H 0.170(3) 0.857(2) 0.4859(18) 0.029(5) Uiso 1 1 d . . . H14A H 0.739(3) 1.022(2) 1.0598(18) 0.028(5) Uiso 1 1 d . . . H25A H 0.750(3) 0.906(2) 0.5420(18) 0.028(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0244(6) 0.0157(5) 0.0250(6) 0.0009(4) 0.0105(5) -0.0009(4) C1 0.0502(12) 0.0301(10) 0.0314(10) 0.0125(8) 0.0181(9) 0.0061(8) C2 0.0265(8) 0.0200(8) 0.0249(8) 0.0035(6) 0.0088(7) 0.0023(6) C3 0.0210(8) 0.0148(7) 0.0208(8) 0.0037(6) 0.0071(6) 0.0004(6) C4 0.0210(8) 0.0184(8) 0.0236(8) 0.0053(6) 0.0071(6) 0.0039(6) C5 0.0183(7) 0.0166(7) 0.0236(8) 0.0029(6) 0.0082(6) 0.0007(6) O2 0.0217(6) 0.0267(6) 0.0153(5) 0.0050(4) 0.0045(4) 0.0043(5) C11 0.0324(10) 0.0339(10) 0.0384(11) 0.0110(8) 0.0078(8) -0.0048(8) C12 0.0246(8) 0.0259(8) 0.0202(8) 0.0060(6) 0.0047(6) 0.0020(6) C13 0.0185(7) 0.0212(7) 0.0158(7) 0.0064(6) 0.0049(6) 0.0021(6) C14 0.0162(7) 0.0234(8) 0.0197(8) 0.0054(6) 0.0048(6) 0.0044(6) C15 0.0216(8) 0.0195(8) 0.0195(8) 0.0061(6) 0.0043(6) 0.0051(6) O3 0.0204(6) 0.0222(6) 0.0244(6) 0.0136(5) 0.0042(5) 0.0004(4) C21 0.0633(15) 0.0364(11) 0.0382(11) 0.0107(9) 0.0274(11) 0.0164(10) C22 0.0339(9) 0.0274(9) 0.0227(8) 0.0110(7) 0.0106(7) 0.0045(7) C23 0.0208(7) 0.0178(7) 0.0196(7) 0.0086(6) 0.0055(6) 0.0021(6) C24 0.0184(7) 0.0215(8) 0.0222(8) 0.0094(6) 0.0013(6) -0.0039(6) C25 0.0167(7) 0.0250(8) 0.0217(8) 0.0109(7) 0.0002(6) -0.0008(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4426(18) . yes O1 HA 0.86(2) . yes C1 C2 1.184(3) . yes C1 H1 0.96(3) . yes C2 C3 1.488(2) . yes C3 C5 1.542(2) 2_766 yes C3 C4 1.543(2) . yes C4 C5 1.531(2) . yes C4 H4A 1.016(18) . yes C4 H4B 0.98(2) . yes C5 C3 1.542(2) 2_766 yes C5 H5B 0.979(19) . yes C5 H5A 0.997(17) . yes O2 C13 1.4441(18) . yes O2 HB 0.88(2) . yes C11 C12 1.187(3) . yes C11 H11 0.96(3) . yes C12 C13 1.484(2) . yes C13 C15 1.535(2) 2_777 yes C13 C14 1.540(2) . yes C14 C15 1.531(2) . yes C14 H14B 0.980(19) . yes C14 H14A 1.00(2) . yes C15 C13 1.535(2) 2_777 yes C15 H15B 1.01(2) . yes C15 H15A 1.014(19) . yes O3 C23 1.4411(18) . yes O3 HC 0.86(3) . yes C21 C22 1.186(3) . yes C21 H21 0.94(3) . yes C22 C23 1.480(2) . yes C23 C24 1.537(2) . yes C23 C25 1.539(2) . yes C24 C25 1.530(2) 2_676 yes C24 H24B 1.02(2) . yes C24 H24A 0.99(2) . yes C25 C24 1.530(2) 2_676 yes C25 H25B 1.00(2) . yes C25 H25A 1.01(2) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 HA 107.2(14) . . yes C2 C1 H1 177.2(17) . . yes C1 C2 C3 177.53(19) . . yes O1 C3 C2 110.12(13) . . yes O1 C3 C5 110.28(12) . 2_766 yes C2 C3 C5 109.15(13) . 2_766 yes O1 C3 C4 107.28(12) . . yes C2 C3 C4 109.46(13) . . yes C5 C3 C4 110.54(12) 2_766 . yes C5 C4 C3 112.56(13) . . yes C5 C4 H4A 110.3(10) . . yes C3 C4 H4A 108.1(10) . . yes C5 C4 H4B 110.0(11) . . yes C3 C4 H4B 108.5(11) . . yes H4A C4 H4B 107.1(15) . . yes C4 C5 C3 112.23(12) . 2_766 yes C4 C5 H5B 109.2(11) . . yes C3 C5 H5B 108.2(11) 2_766 . yes C4 C5 H5A 109.9(10) . . yes C3 C5 H5A 108.2(10) 2_766 . yes H5B C5 H5A 109.1(15) . . yes C13 O2 HB 108.2(15) . . yes C12 C11 H11 177.8(16) . . yes C11 C12 C13 177.03(19) . . yes O2 C13 C12 109.12(12) . . yes O2 C13 C15 106.79(12) . 2_777 yes C12 C13 C15 111.25(13) . 2_777 yes O2 C13 C14 109.87(12) . . yes C12 C13 C14 109.64(13) . . yes C15 C13 C14 110.13(12) 2_777 . yes C15 C14 C13 111.89(12) . . yes C15 C14 H14B 109.6(11) . . yes C13 C14 H14B 108.7(11) . . yes C15 C14 H14A 109.4(11) . . yes C13 C14 H14A 109.0(11) . . yes H14B C14 H14A 108.2(15) . . yes C14 C15 C13 111.55(13) . 2_777 yes C14 C15 H15B 109.5(11) . . yes C13 C15 H15B 107.3(11) 2_777 . yes C14 C15 H15A 110.6(11) . . yes C13 C15 H15A 108.8(11) 2_777 . yes H15B C15 H15A 109.0(15) . . yes C23 O3 HC 112.1(16) . . yes C22 C21 H21 176.9(19) . . yes C21 C22 C23 178.14(19) . . yes O3 C23 C22 110.22(12) . . yes O3 C23 C24 110.42(12) . . yes C22 C23 C24 110.20(13) . . yes O3 C23 C25 105.86(12) . . yes C22 C23 C25 110.61(13) . . yes C24 C23 C25 109.45(12) . . yes C25 C24 C23 111.99(13) 2_676 . yes C25 C24 H24B 110.6(11) 2_676 . yes C23 C24 H24B 106.7(11) . . yes C25 C24 H24A 110.6(11) 2_676 . yes C23 C24 H24A 108.1(11) . . yes H24B C24 H24A 108.6(16) . . yes C24 C25 C23 111.38(13) 2_676 . yes C24 C25 H25B 109.0(11) 2_676 . yes C23 C25 H25B 110.1(11) . . yes C24 C25 H25A 111.3(11) 2_676 . yes C23 C25 H25A 106.9(11) . . yes H25B C25 H25A 108.1(15) . . yes #===END data_3 _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_length_neutron _atom_type_scat_source 'C' 'C' 6.646 'International Tables Vol C Tables 4.4.4.1' 'H' 'H' -3.739 'International Tables Vol C Tables 4.4.4.1' 'O' 'O' 5.803 'International Tables Vol C Tables 4.4.4.1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.925(2) _cell_length_b 6.1343(12) _cell_length_c 16.725(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.12(3) _cell_angle_gamma 90.00 _cell_volume 987.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 2 _exptl_crystal_size_mid 2 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 126 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 1.17 + 1.09 * lambda [cm^-1] ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 25 reflections (hence _cell_measurement_reflns_used 25), was used. For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations. Because of the kind of experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of cell_measurement_sin(theta)/lambda_min 0..20 cell_measurement_sin(theta)/lambda_max 0.60 The same applies for the wavelength used for the experiment. The full range of wavelengths for which data were collected was 0.5-5 Angstroms, BUT the bulk of the diffraction information is obtained from wavelength in the range 0.7-2.5 Angstroms. ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.5-5.0 _diffrn_radiation_type neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'SXD' _diffrn_measurement_method 'Time of flight LAUE diffraction' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9863 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 23.54 _reflns_number_total 2661 _reflns_number_gt 2659 _reflns_threshold_expression 2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_extinction_coef 0.23 _refine_ls_number_reflns 2661 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0888 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 3.792 _refine_ls_restrained_S_all 3.792 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 2.242 _refine_diff_density_min -1.708 _refine_diff_density_rms 0.341 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5801(3) 0.0888(4) 0.85373(17) 0.0159(5) Uani 1 1 d . . . HA H 0.6079(6) -0.0334(8) 0.8222(3) 0.0292(10) Uani 1 1 d . . . C1 C 0.3001(3) -0.2507(4) 0.83121(17) 0.0247(5) Uani 1 1 d . . . H1 H 0.2194(7) -0.3582(10) 0.7981(5) 0.0556(18) Uani 1 1 d . . . C2 C 0.3916(2) -0.1333(4) 0.86785(15) 0.0160(4) Uani 1 1 d . . . C3 C 0.5089(2) 0.0038(3) 0.91205(14) 0.0126(4) Uani 1 1 d . . . C4 C 0.6073(2) -0.1359(4) 0.97772(14) 0.0148(4) Uani 1 1 d . . . H4A H 0.6394(6) -0.2792(8) 0.9481(3) 0.0325(11) Uani 1 1 d . . . H4B H 0.6998(5) -0.0353(8) 1.0031(3) 0.0281(10) Uani 1 1 d . . . C5 C 0.5409(2) -0.2021(3) 1.04709(14) 0.0141(4) Uani 1 1 d . . . H5A H 0.6164(5) -0.2963(8) 1.0940(3) 0.0307(11) Uani 1 1 d . . . H5B H 0.4490(5) -0.3051(8) 1.0232(3) 0.0309(11) Uani 1 1 d . . . O2 O 0.7598(3) -0.5574(4) 0.87393(18) 0.0193(5) Uani 1 1 d . . . HB H 0.7106(5) -0.7004(8) 0.8710(3) 0.0298(11) Uani 1 1 d . . . C11 C 1.0574(3) -0.7927(5) 0.8400(2) 0.0386(7) Uani 1 1 d . . . H11 H 1.1209(10) -0.8862(18) 0.8088(6) 0.088(3) Uani 1 1 d . . . C12 C 0.9860(3) -0.6958(4) 0.87693(18) 0.0241(5) Uani 1 1 d . . . C13 C 0.8997(2) -0.5704(3) 0.92163(15) 0.0156(4) Uani 1 1 d . . . C14 C 0.9528(2) -0.3356(4) 0.93489(16) 0.0180(5) Uani 1 1 d . . . H14A H 0.9541(6) -0.2630(8) 0.8757(3) 0.0350(12) Uani 1 1 d . . . H14B H 0.8757(5) -0.2439(8) 0.9601(4) 0.0336(12) Uani 1 1 d . . . C15 C 0.9033(2) -0.6780(4) 1.00513(16) 0.0189(5) Uani 1 1 d . . . H15A H 0.8719(6) -0.8473(9) 0.9963(4) 0.0377(13) Uani 1 1 d . . . H15B H 0.8261(5) -0.5960(9) 1.0322(4) 0.0361(13) Uani 1 1 d . . . O3 O 0.3478(3) 0.2265(5) 0.2343(2) 0.0210(5) Uani 1 1 d . . . HC H 0.4305(6) 0.2810(10) 0.2742(4) 0.0389(13) Uani 1 1 d . . . HD H 0.3101(6) 0.3525(9) 0.2017(4) 0.0384(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0197(12) 0.0137(11) 0.0160(12) -0.0016(10) 0.0078(10) -0.0046(9) HA 0.038(3) 0.025(2) 0.028(3) -0.005(2) 0.015(2) 0.0006(19) C1 0.0246(12) 0.0230(12) 0.0240(12) -0.0057(10) 0.0013(9) -0.0094(9) H1 0.052(4) 0.047(3) 0.059(5) -0.012(3) -0.002(3) -0.028(3) C2 0.0167(10) 0.0140(9) 0.0173(11) -0.0027(8) 0.0044(8) -0.0020(8) C3 0.0144(9) 0.0106(8) 0.0133(10) -0.0021(8) 0.0042(7) 0.0000(7) C4 0.0141(9) 0.0172(10) 0.0140(10) -0.0010(8) 0.0052(8) 0.0020(8) H4A 0.040(3) 0.028(2) 0.033(3) -0.010(2) 0.015(2) 0.010(2) H4B 0.021(2) 0.026(2) 0.035(3) 0.000(2) 0.0038(19) -0.0056(17) C5 0.0174(9) 0.0120(9) 0.0131(10) 0.0004(8) 0.0043(8) 0.0011(8) H5A 0.038(3) 0.027(2) 0.025(2) 0.005(2) 0.004(2) 0.010(2) H5B 0.031(2) 0.030(2) 0.032(3) -0.002(2) 0.007(2) -0.006(2) O2 0.0134(11) 0.0185(12) 0.0230(14) -0.0003(11) -0.0012(10) -0.0018(9) HB 0.028(2) 0.025(2) 0.035(3) -0.006(2) 0.003(2) -0.0094(18) C11 0.0383(16) 0.0461(17) 0.0344(17) -0.0122(14) 0.0145(13) 0.0132(14) H11 0.082(6) 0.124(7) 0.062(6) -0.022(5) 0.026(5) 0.056(6) C12 0.0247(12) 0.0236(11) 0.0246(13) -0.0067(10) 0.0070(10) 0.0046(10) C13 0.0148(10) 0.0141(9) 0.0173(11) 0.0006(8) 0.0027(8) -0.0017(8) C14 0.0173(10) 0.0157(10) 0.0202(12) 0.0024(9) 0.0028(9) -0.0016(8) H14A 0.042(3) 0.032(3) 0.028(3) 0.011(2) 0.003(2) -0.014(2) H14B 0.028(2) 0.025(2) 0.048(3) -0.001(2) 0.009(2) 0.005(2) C15 0.0134(10) 0.0198(11) 0.0237(12) 0.0009(9) 0.0052(9) -0.0042(8) H15A 0.035(3) 0.032(2) 0.045(3) 0.008(2) 0.006(2) -0.009(2) H15B 0.020(2) 0.045(3) 0.045(4) 0.003(3) 0.011(2) 0.001(2) O3 0.0270(13) 0.0178(12) 0.0188(13) -0.0014(11) 0.0069(11) 0.0008(11) HC 0.039(3) 0.048(3) 0.027(3) -0.008(2) 0.002(2) 0.006(3) HD 0.042(3) 0.032(3) 0.041(3) 0.010(2) 0.009(3) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.435(3) . yes O1 HA 0.993(6) . yes C1 C2 1.203(3) . yes C1 H1 1.080(6) . yes C2 C3 1.479(3) . yes C3 C5 1.535(3) 3_657 yes C3 C4 1.540(3) . yes C4 C5 1.523(3) . yes C4 H4A 1.094(5) . yes C4 H4B 1.102(5) . yes C5 C3 1.535(3) 3_657 yes C5 H5A 1.107(5) . yes C5 H5B 1.101(6) . yes O2 C13 1.425(4) . yes O2 HB 1.000(6) . yes C11 C12 1.205(4) . yes C11 H11 1.076(8) . yes C12 C13 1.482(4) . yes C13 C14 1.531(3) . yes C13 C15 1.537(3) . yes C14 C15 1.534(3) 3_747 yes C14 H14A 1.089(6) . yes C14 H14B 1.112(6) . yes C15 C14 1.534(3) 3_747 yes C15 H15A 1.084(6) . yes C15 H15B 1.102(6) . yes O3 HC 0.982(8) . yes O3 HD 0.967(7) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 HA 109.4(4) . . yes C2 C1 H1 178.9(5) . . yes C1 C2 C3 177.3(2) . . yes O1 C3 C2 109.0(2) . . yes O1 C3 C5 106.25(18) . 3_657 yes C2 C3 C5 111.95(17) . 3_657 yes O1 C3 C4 110.79(19) . . yes C2 C3 C4 108.97(17) . . yes C5 C3 C4 109.90(18) 3_657 . yes C5 C4 C3 112.01(17) . . yes C5 C4 H4A 111.0(4) . . yes C3 C4 H4A 109.2(3) . . yes C5 C4 H4B 109.3(4) . . yes C3 C4 H4B 106.7(3) . . yes H4A C4 H4B 108.5(4) . . yes C4 C5 C3 111.94(17) . 3_657 yes C4 C5 H5A 109.6(3) . . yes C3 C5 H5A 109.5(3) 3_657 . yes C4 C5 H5B 110.5(3) . . yes C3 C5 H5B 106.8(3) 3_657 . yes H5A C5 H5B 108.4(4) . . yes C13 O2 HB 112.0(4) . . yes C12 C11 H11 177.1(8) . . yes C11 C12 C13 178.3(3) . . yes O2 C13 C12 110.5(2) . . yes O2 C13 C14 106.4(2) . . yes C12 C13 C14 109.9(2) . . yes O2 C13 C15 109.7(2) . . yes C12 C13 C15 110.32(19) . . yes C14 C13 C15 109.96(19) . . yes C13 C14 C15 112.25(19) . 3_747 yes C13 C14 H14A 109.5(3) . . yes C15 C14 H14A 110.9(3) 3_747 . yes C13 C14 H14B 106.7(3) . . yes C15 C14 H14B 109.9(4) 3_747 . yes H14A C14 H14B 107.4(5) . . yes C14 C15 C13 112.47(18) 3_747 . yes C14 C15 H15A 109.4(4) 3_747 . yes C13 C15 H15A 110.2(4) . . yes C14 C15 H15B 109.6(4) 3_747 . yes C13 C15 H15B 108.2(4) . . yes H15A C15 H15B 106.7(5) . . yes HC O3 HD 104.8(6) . . yes