# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Philip Coppens' _publ_contact_author_address ; Department of Chemistry State University of New York at Buffalo Buffalo New York 14260-3000 UNITED STATES OF AMERICA ; _publ_contact_author_email COPPENS@BUFFALO.EDU _publ_section_title ; Hydrogen-bond quenching of photodecarbonylation in the solid state and recovery of reactivity by crystal engineering ; loop_ _publ_author_name P.Coppens M.Gembicky M.Messerschmidt 'Jing Zhang.' data_HOTMK _database_code_depnum_ccdc_archive 'CCDC 630992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2, 2, 4, 4-Tetramethyl -1,3 di(4-hydroxylphenyl)acetone' _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 O3' _chemical_formula_sum 'C19 H22 O3' _chemical_formula_weight 298.37 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 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 10.0719(2) _cell_length_b 11.2639(2) _cell_length_c 14.2688(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.7710(10) _cell_angle_gamma 90.00 _cell_volume 1599.85(5) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 3310 _cell_measurement_theta_min 2.879 _cell_measurement_theta_max 26.134 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'empirical SADABS' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'Blessing, R. (1995) Acta Crystallogr., A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14699 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3682 _reflns_number_gt 3214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0466P)^2^+0.6029P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3682 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.29511(7) 0.55502(7) 0.89432(5) 0.01605(17) Uani 1 1 d . . . O2 O -0.22315(8) 0.83959(7) 1.07868(6) 0.01904(18) Uani 1 1 d . . . H2A H -0.2351(16) 0.7790(16) 1.1167(12) 0.037(4) Uiso 1 1 d . . . O3 O 0.74550(8) 0.84601(7) 0.70087(5) 0.01631(17) Uani 1 1 d . . . H3A H 0.7364(16) 0.9194(16) 0.6783(12) 0.038(4) Uiso 1 1 d . . . C1 C 0.27145(10) 0.66166(9) 0.89288(7) 0.0121(2) Uani 1 1 d . . . C2 C 0.14508(10) 0.70918(9) 0.82876(7) 0.0132(2) Uani 1 1 d . . . C3 C 0.37304(10) 0.74332(9) 0.95512(7) 0.0128(2) Uani 1 1 d . . . C4 C 0.08163(11) 0.60872(10) 0.76372(8) 0.0174(2) Uani 1 1 d . . . H4C H 0.0603 0.5416 0.8025 0.026 Uiso 1 1 calc R . . H4B H 0.1451 0.5830 0.7221 0.026 Uiso 1 1 calc R . . H4A H -0.0009 0.6376 0.7251 0.026 Uiso 1 1 calc R . . C5 C 0.17967(11) 0.81016(10) 0.76387(7) 0.0163(2) Uani 1 1 d . . . H5C H 0.0990 0.8328 0.7201 0.024 Uiso 1 1 calc R . . H5B H 0.2491 0.7831 0.7275 0.024 Uiso 1 1 calc R . . H5A H 0.2130 0.8788 0.8026 0.024 Uiso 1 1 calc R . . C6 C 0.31055(11) 0.85266(9) 0.99503(7) 0.0151(2) Uani 1 1 d . . . H6C H 0.3816 0.9010 1.0310 0.023 Uiso 1 1 calc R . . H6B H 0.2473 0.8272 1.0369 0.023 Uiso 1 1 calc R . . H6A H 0.2628 0.8997 0.9427 0.023 Uiso 1 1 calc R . . C7 C 0.44177(11) 0.67123(10) 1.04083(7) 0.0168(2) Uani 1 1 d . . . H7C H 0.5073 0.7215 1.0803 0.025 Uiso 1 1 calc R . . H7B H 0.4877 0.6026 1.0183 0.025 Uiso 1 1 calc R . . H7A H 0.3739 0.6438 1.0783 0.025 Uiso 1 1 calc R . . C8 C 0.04555(10) 0.74554(9) 0.89514(7) 0.0127(2) Uani 1 1 d . . . C9 C 0.01191(11) 0.66427(9) 0.96154(8) 0.0163(2) Uani 1 1 d . . . H9A H 0.0513 0.5875 0.9648 0.020 Uiso 1 1 calc R . . C10 C -0.07768(11) 0.69290(10) 1.02294(8) 0.0175(2) Uani 1 1 d . . . H10A H -0.0991 0.6361 1.0675 0.021 Uiso 1 1 calc R . . C11 C -0.13619(10) 0.80538(9) 1.01889(7) 0.0144(2) Uani 1 1 d . . . C12 C -0.10432(10) 0.88691(9) 0.95297(8) 0.0152(2) Uani 1 1 d . . . H12A H -0.1442 0.9635 0.9494 0.018 Uiso 1 1 calc R . . C13 C -0.01449(10) 0.85701(9) 0.89225(7) 0.0143(2) Uani 1 1 d . . . H13A H 0.0066 0.9139 0.8476 0.017 Uiso 1 1 calc R . . C14 C 0.47628(10) 0.77573(9) 0.88985(7) 0.0127(2) Uani 1 1 d . . . C15 C 0.55509(10) 0.68652(9) 0.85756(7) 0.0147(2) Uani 1 1 d . . . H15A H 0.5467 0.6073 0.8787 0.018 Uiso 1 1 calc R . . C16 C 0.64504(10) 0.71105(9) 0.79554(8) 0.0155(2) Uani 1 1 d . . . H16A H 0.6979 0.6493 0.7749 0.019 Uiso 1 1 calc R . . C17 C 0.65723(10) 0.82649(9) 0.76385(7) 0.0138(2) Uani 1 1 d . . . C18 C 0.58223(10) 0.91704(9) 0.79592(7) 0.0149(2) Uani 1 1 d . . . H18A H 0.5920 0.9963 0.7753 0.018 Uiso 1 1 calc R . . C19 C 0.49271(10) 0.89137(9) 0.85843(7) 0.0144(2) Uani 1 1 d . . . H19A H 0.4418 0.9538 0.8801 0.017 Uiso 1 1 calc R . . 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 0.0174(4) 0.0115(4) 0.0196(4) -0.0008(3) 0.0038(3) 0.0011(3) O2 0.0204(4) 0.0178(4) 0.0211(4) 0.0004(3) 0.0101(3) 0.0034(3) O3 0.0181(4) 0.0141(4) 0.0182(4) 0.0023(3) 0.0074(3) -0.0004(3) C1 0.0130(5) 0.0135(5) 0.0109(5) 0.0000(4) 0.0056(4) -0.0008(4) C2 0.0138(5) 0.0133(5) 0.0125(5) -0.0003(4) 0.0022(4) 0.0002(4) C3 0.0142(5) 0.0119(5) 0.0125(5) -0.0007(4) 0.0026(4) -0.0002(4) C4 0.0175(5) 0.0174(5) 0.0166(5) -0.0041(4) 0.0007(4) -0.0004(4) C5 0.0179(5) 0.0181(5) 0.0134(5) 0.0020(4) 0.0041(4) 0.0011(4) C6 0.0164(5) 0.0141(5) 0.0152(5) -0.0035(4) 0.0036(4) -0.0005(4) C7 0.0184(5) 0.0186(5) 0.0130(5) 0.0009(4) 0.0013(4) 0.0018(4) C8 0.0114(4) 0.0132(5) 0.0132(5) -0.0014(4) 0.0012(4) -0.0006(4) C9 0.0178(5) 0.0111(5) 0.0208(5) 0.0010(4) 0.0055(4) 0.0026(4) C10 0.0201(5) 0.0145(5) 0.0193(5) 0.0037(4) 0.0071(4) 0.0005(4) C11 0.0125(5) 0.0163(5) 0.0147(5) -0.0024(4) 0.0025(4) 0.0000(4) C12 0.0146(5) 0.0117(5) 0.0187(5) -0.0001(4) 0.0009(4) 0.0025(4) C13 0.0147(5) 0.0129(5) 0.0151(5) 0.0025(4) 0.0011(4) 0.0000(4) C14 0.0121(4) 0.0135(5) 0.0122(5) -0.0007(4) 0.0009(4) -0.0011(4) C15 0.0162(5) 0.0117(5) 0.0164(5) 0.0011(4) 0.0030(4) -0.0002(4) C16 0.0160(5) 0.0136(5) 0.0175(5) -0.0010(4) 0.0043(4) 0.0017(4) C17 0.0124(5) 0.0163(5) 0.0126(5) -0.0004(4) 0.0015(4) -0.0023(4) C18 0.0159(5) 0.0114(5) 0.0173(5) 0.0006(4) 0.0020(4) -0.0017(4) C19 0.0146(5) 0.0118(5) 0.0167(5) -0.0026(4) 0.0018(4) -0.0001(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 C1 1.2242(13) . ? O2 C11 1.3680(12) . ? O2 H2A 0.892(18) . ? O3 C17 1.3749(12) . ? O3 H3A 0.887(18) . ? C1 C2 1.5455(14) . ? C1 C3 1.5507(14) . ? C2 C8 1.5360(14) . ? C2 C4 1.5392(14) . ? C2 C5 1.5397(14) . ? C3 C6 1.5318(14) . ? C3 C7 1.5415(14) . ? C3 C14 1.5418(14) . ? C4 H4C 0.9800 . ? C4 H4B 0.9800 . ? C4 H4A 0.9800 . ? C5 H5C 0.9800 . ? C5 H5B 0.9800 . ? C5 H5A 0.9800 . ? C6 H6C 0.9800 . ? C6 H6B 0.9800 . ? C6 H6A 0.9800 . ? C7 H7C 0.9800 . ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C8 C13 1.3915(14) . ? C8 C9 1.3958(14) . ? C9 C10 1.3880(14) . ? C9 H9A 0.9500 . ? C10 C11 1.3948(15) . ? C10 H10A 0.9500 . ? C11 C12 1.3868(15) . ? C12 C13 1.3862(15) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C19 1.3956(14) . ? C14 C15 1.4013(14) . ? C15 C16 1.3874(14) . ? C15 H15A 0.9500 . ? C16 C17 1.3883(15) . ? C16 H16A 0.9500 . ? C17 C18 1.3877(15) . ? C18 C19 1.3919(14) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? 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 C11 O2 H2A 108.8(10) . . ? C17 O3 H3A 110.2(11) . . ? O1 C1 C2 119.37(9) . . ? O1 C1 C3 117.56(9) . . ? C2 C1 C3 123.06(9) . . ? C8 C2 C4 108.53(8) . . ? C8 C2 C5 113.75(9) . . ? C4 C2 C5 106.96(8) . . ? C8 C2 C1 106.46(8) . . ? C4 C2 C1 109.33(8) . . ? C5 C2 C1 111.74(8) . . ? C6 C3 C7 106.79(8) . . ? C6 C3 C14 112.79(8) . . ? C7 C3 C14 109.95(8) . . ? C6 C3 C1 114.66(8) . . ? C7 C3 C1 108.61(8) . . ? C14 C3 C1 103.97(8) . . ? C2 C4 H4C 109.5 . . ? C2 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? C2 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? C2 C5 H5C 109.5 . . ? C2 C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? C2 C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? C3 C6 H6C 109.5 . . ? C3 C6 H6B 109.5 . . ? H6C C6 H6B 109.5 . . ? C3 C6 H6A 109.5 . . ? H6C C6 H6A 109.5 . . ? H6B C6 H6A 109.5 . . ? C3 C7 H7C 109.5 . . ? C3 C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? C3 C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? C13 C8 C9 117.55(9) . . ? C13 C8 C2 122.94(9) . . ? C9 C8 C2 119.51(9) . . ? C10 C9 C8 121.64(10) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 119.74(10) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? O2 C11 C12 118.22(9) . . ? O2 C11 C10 122.46(10) . . ? C12 C11 C10 119.31(10) . . ? C13 C12 C11 120.24(10) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C12 C13 C8 121.52(10) . . ? C12 C13 H13A 119.2 . . ? C8 C13 H13A 119.2 . . ? C19 C14 C15 117.57(9) . . ? C19 C14 C3 122.61(9) . . ? C15 C14 C3 119.80(9) . . ? C16 C15 C14 121.65(10) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 119.54(10) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? O3 C17 C18 122.47(9) . . ? O3 C17 C16 117.44(9) . . ? C18 C17 C16 120.10(10) . . ? C17 C18 C19 119.80(10) . . ? C17 C18 H18A 120.1 . . ? C19 C18 H18A 120.1 . . ? C18 C19 C14 121.33(10) . . ? C18 C19 H19A 119.3 . . ? C14 C19 H19A 119.3 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 # Attachment '630994-2.cif' #============================================================ data_MonoHO _database_code_depnum_ccdc_archive 'CCDC 630993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2, 2, 4, 4-tetramethyl -1-(4-hydroxyphenyl)-3-(4- methoxyphenyl)acetone ; _chemical_melting_point ? _chemical_formula_moiety '2(C20 H24 O3), H2 O' _chemical_formula_sum 'C40 H50 O7' _chemical_formula_weight 642.80 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.517(3) _cell_length_b 6.3855(13) _cell_length_c 21.558(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.98(3) _cell_angle_gamma 90.00 _cell_volume 1722.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 5790 _cell_measurement_theta_min 2.835 _cell_measurement_theta_max 28.262 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type 'empirical SADABS' _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'Blessing, R. (1995) Acta Crystallogr., A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21014 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.21 _reflns_number_total 8471 _reflns_number_gt 7987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0615P)^2^+0.2826P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(6) _refine_ls_number_reflns 8471 _refine_ls_number_parameters 440 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.59739(8) 0.19067(18) 0.24659(4) 0.0234(2) Uani 1 1 d . . . O2 O 0.33507(8) 0.65130(17) 0.00130(4) 0.0221(2) Uani 1 1 d . . . H2A H 0.2916(15) 0.558(3) -0.0046(9) 0.037(5) Uiso 1 1 d . . . O3 O 0.86061(7) 0.77767(16) 0.47253(4) 0.0203(2) Uani 1 1 d . . . O4 O -0.09154(8) 0.82012(17) -0.24964(4) 0.0224(2) Uani 1 1 d . . . O5 O 0.17112(8) 0.36705(19) -0.01338(5) 0.0248(2) Uani 1 1 d . . . H5A H 0.1858(16) 0.239(4) -0.0087(10) 0.044(6) Uiso 1 1 d . . . O6 O -0.36571(7) 0.24193(16) -0.47590(4) 0.0206(2) Uani 1 1 d . . . O7 O 0.20047(8) -0.02197(16) 0.01729(5) 0.0261(2) Uani 1 1 d . . . H7D H 0.2584(14) -0.113(3) 0.0090(8) 0.032(5) Uiso 1 1 d . . . H7E H 0.1626(17) -0.074(4) 0.0474(10) 0.057(6) Uiso 1 1 d . . . C1 C 0.59812(9) 0.3801(2) 0.24413(5) 0.0155(3) Uani 1 1 d . . . C2 C 0.65284(9) 0.4891(2) 0.18888(5) 0.0162(2) Uani 1 1 d . . . C3 C 0.54335(10) 0.5058(2) 0.29619(5) 0.0159(2) Uani 1 1 d . . . C4 C 0.73114(10) 0.3335(3) 0.15976(6) 0.0238(3) Uani 1 1 d . . . H4A H 0.7665 0.4004 0.1247 0.036 Uiso 1 1 calc R . . H4B H 0.6919 0.2098 0.1451 0.036 Uiso 1 1 calc R . . H4C H 0.7849 0.2913 0.1909 0.036 Uiso 1 1 calc R . . C5 C 0.71838(10) 0.6823(2) 0.20875(6) 0.0204(3) Uani 1 1 d . . . H5B H 0.7510 0.7454 0.1722 0.031 Uiso 1 1 calc R . . H5C H 0.7745 0.6399 0.2384 0.031 Uiso 1 1 calc R . . H5D H 0.6713 0.7847 0.2283 0.031 Uiso 1 1 calc R . . C6 C 0.47293(10) 0.6843(2) 0.27039(6) 0.0205(3) Uani 1 1 d . . . H6A H 0.4400 0.7593 0.3048 0.031 Uiso 1 1 calc R . . H6B H 0.4169 0.6259 0.2432 0.031 Uiso 1 1 calc R . . H6C H 0.5170 0.7815 0.2467 0.031 Uiso 1 1 calc R . . C7 C 0.46949(10) 0.3562(2) 0.33161(6) 0.0221(3) Uani 1 1 d . . . H7A H 0.4340 0.4332 0.3648 0.033 Uiso 1 1 calc R . . H7B H 0.5119 0.2418 0.3497 0.033 Uiso 1 1 calc R . . H7C H 0.4155 0.2984 0.3029 0.033 Uiso 1 1 calc R . . C8 C 0.56486(9) 0.5398(2) 0.14054(5) 0.0156(2) Uani 1 1 d . . . C9 C 0.49689(10) 0.3785(2) 0.11986(5) 0.0168(3) Uani 1 1 d . . . H9A H 0.5039 0.2430 0.1376 0.020 Uiso 1 1 calc R . . C10 C 0.41968(10) 0.4130(2) 0.07403(5) 0.0175(3) Uani 1 1 d . . . H10A H 0.3745 0.3018 0.0605 0.021 Uiso 1 1 calc R . . C11 C 0.40876(10) 0.6110(2) 0.04803(5) 0.0164(2) Uani 1 1 d . . . C12 C 0.47454(10) 0.7741(2) 0.06809(6) 0.0199(3) Uani 1 1 d . . . H12A H 0.4668 0.9100 0.0506 0.024 Uiso 1 1 calc R . . C13 C 0.55154(10) 0.7367(2) 0.11394(5) 0.0183(3) Uani 1 1 d . . . H13A H 0.5963 0.8485 0.1275 0.022 Uiso 1 1 calc R . . C14 C 0.63115(9) 0.5825(2) 0.34147(5) 0.0139(2) Uani 1 1 d . . . C15 C 0.70733(9) 0.4411(2) 0.36397(5) 0.0154(2) Uani 1 1 d . . . H15A H 0.7060 0.3010 0.3492 0.019 Uiso 1 1 calc R . . C16 C 0.78530(10) 0.4991(2) 0.40747(5) 0.0157(3) Uani 1 1 d . . . H16A H 0.8364 0.3996 0.4219 0.019 Uiso 1 1 calc R . . C17 C 0.78787(10) 0.7036(2) 0.42968(5) 0.0160(3) Uani 1 1 d . . . C18 C 0.71251(10) 0.8482(2) 0.40795(6) 0.0184(3) Uani 1 1 d . . . H18A H 0.7136 0.9878 0.4232 0.022 Uiso 1 1 calc R . . C19 C 0.63572(11) 0.7882(2) 0.36399(5) 0.0180(3) Uani 1 1 d . . . H19A H 0.5855 0.8885 0.3490 0.022 Uiso 1 1 calc R . . C20 C 0.93801(10) 0.6306(2) 0.49505(6) 0.0197(3) Uani 1 1 d . . . H20A H 0.9855 0.6992 0.5254 0.030 Uiso 1 1 calc R . . H20B H 0.9801 0.5785 0.4604 0.030 Uiso 1 1 calc R . . H20C H 0.9015 0.5131 0.5149 0.030 Uiso 1 1 calc R . . C21 C -0.09608(9) 0.6296(2) -0.25011(5) 0.0143(2) Uani 1 1 d . . . C22 C -0.15486(9) 0.5170(2) -0.19704(5) 0.0150(2) Uani 1 1 d . . . C23 C -0.04207(9) 0.5070(2) -0.30294(5) 0.0143(2) Uani 1 1 d . . . C24 C -0.23699(10) 0.6722(3) -0.17015(6) 0.0232(3) Uani 1 1 d . . . H24A H -0.2756 0.6044 -0.1365 0.035 Uiso 1 1 calc R . . H24B H -0.2878 0.7144 -0.2029 0.035 Uiso 1 1 calc R . . H24C H -0.1996 0.7962 -0.1541 0.035 Uiso 1 1 calc R . . C25 C -0.21715(10) 0.3227(2) -0.21761(6) 0.0198(3) Uani 1 1 d . . . H25A H -0.2518 0.2600 -0.1817 0.030 Uiso 1 1 calc R . . H25B H -0.1680 0.2210 -0.2357 0.030 Uiso 1 1 calc R . . H25C H -0.2716 0.3624 -0.2486 0.030 Uiso 1 1 calc R . . C26 C 0.03062(10) 0.6590(2) -0.33812(6) 0.0203(3) Uani 1 1 d . . . H26A H 0.0659 0.5838 -0.3717 0.030 Uiso 1 1 calc R . . H26B H 0.0847 0.7164 -0.3095 0.030 Uiso 1 1 calc R . . H26C H -0.0125 0.7734 -0.3556 0.030 Uiso 1 1 calc R . . C27 C 0.02932(10) 0.3297(2) -0.27770(6) 0.0188(3) Uani 1 1 d . . . H27A H 0.0621 0.2558 -0.3124 0.028 Uiso 1 1 calc R . . H27B H -0.0140 0.2313 -0.2540 0.028 Uiso 1 1 calc R . . H27C H 0.0854 0.3887 -0.2507 0.028 Uiso 1 1 calc R . . C28 C -0.06889(9) 0.4691(2) -0.14730(5) 0.0138(2) Uani 1 1 d . . . C29 C -0.00805(10) 0.6318(2) -0.12180(6) 0.0175(3) Uani 1 1 d . . . H29A H -0.0208 0.7710 -0.1356 0.021 Uiso 1 1 calc R . . C30 C 0.07015(10) 0.5966(2) -0.07709(6) 0.0185(3) Uani 1 1 d . . . H30A H 0.1097 0.7109 -0.0602 0.022 Uiso 1 1 calc R . . C31 C 0.09110(10) 0.3939(2) -0.05670(6) 0.0180(3) Uani 1 1 d . . . C32 C 0.03097(10) 0.2285(2) -0.08043(6) 0.0182(2) Uani 1 1 d . . . H32A H 0.0436 0.0900 -0.0660 0.022 Uiso 1 1 calc R . . C33 C -0.04796(10) 0.2662(2) -0.12550(5) 0.0171(3) Uani 1 1 d . . . H33A H -0.0883 0.1521 -0.1417 0.021 Uiso 1 1 calc R . . C34 C -0.13087(10) 0.4327(2) -0.34741(5) 0.0143(2) Uani 1 1 d . . . C35 C -0.20872(9) 0.5740(2) -0.36805(5) 0.0153(2) Uani 1 1 d . . . H35A H -0.2071 0.7133 -0.3526 0.018 Uiso 1 1 calc R . . C36 C -0.28866(10) 0.5178(2) -0.41049(5) 0.0159(3) Uani 1 1 d . . . H36A H -0.3408 0.6172 -0.4236 0.019 Uiso 1 1 calc R . . C37 C -0.29144(10) 0.3134(2) -0.43368(5) 0.0156(2) Uani 1 1 d . . . C38 C -0.21500(10) 0.1694(2) -0.41336(6) 0.0179(3) Uani 1 1 d . . . H38A H -0.2165 0.0302 -0.4289 0.021 Uiso 1 1 calc R . . C39 C -0.13668(10) 0.2281(2) -0.37059(5) 0.0168(3) Uani 1 1 d . . . H39A H -0.0858 0.1274 -0.3567 0.020 Uiso 1 1 calc R . . C40 C -0.44318(10) 0.3903(3) -0.49783(6) 0.0212(3) Uani 1 1 d . . . H40A H -0.4918 0.3223 -0.5277 0.032 Uiso 1 1 calc R . . H40B H -0.4068 0.5071 -0.5181 0.032 Uiso 1 1 calc R . . H40C H -0.4840 0.4433 -0.4628 0.032 Uiso 1 1 calc R . . 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 0.0339(6) 0.0149(5) 0.0214(5) 0.0005(4) -0.0019(4) 0.0009(4) O2 0.0225(5) 0.0203(6) 0.0230(4) 0.0023(4) -0.0079(4) -0.0020(4) O3 0.0232(4) 0.0188(5) 0.0189(4) -0.0016(4) -0.0052(3) -0.0013(4) O4 0.0333(5) 0.0135(5) 0.0205(4) -0.0002(3) -0.0001(4) 0.0004(4) O5 0.0244(5) 0.0210(6) 0.0286(5) 0.0028(4) -0.0154(4) -0.0016(4) O6 0.0226(4) 0.0191(5) 0.0198(4) -0.0025(4) -0.0059(3) -0.0015(4) O7 0.0309(5) 0.0224(5) 0.0251(5) 0.0020(4) 0.0035(4) 0.0039(4) C1 0.0143(6) 0.0157(7) 0.0164(5) -0.0007(5) -0.0041(4) 0.0011(5) C2 0.0145(5) 0.0172(7) 0.0167(5) -0.0013(5) -0.0020(4) -0.0017(5) C3 0.0149(5) 0.0164(7) 0.0165(5) 0.0009(5) -0.0016(4) 0.0009(5) C4 0.0178(6) 0.0281(8) 0.0255(6) -0.0052(6) 0.0004(5) 0.0038(6) C5 0.0183(6) 0.0224(7) 0.0203(6) 0.0000(5) -0.0019(4) -0.0072(5) C6 0.0185(6) 0.0219(7) 0.0209(6) 0.0001(5) -0.0030(5) 0.0074(5) C7 0.0188(6) 0.0246(8) 0.0229(6) 0.0029(5) 0.0012(5) -0.0021(6) C8 0.0142(5) 0.0186(6) 0.0138(5) -0.0003(5) 0.0000(4) -0.0004(5) C9 0.0192(6) 0.0148(6) 0.0164(5) 0.0008(5) -0.0017(4) -0.0026(5) C10 0.0179(6) 0.0176(7) 0.0171(5) -0.0006(5) -0.0023(4) -0.0040(5) C11 0.0159(5) 0.0185(6) 0.0145(5) 0.0006(5) -0.0013(4) -0.0018(5) C12 0.0224(6) 0.0174(7) 0.0199(6) 0.0037(5) -0.0022(5) -0.0020(5) C13 0.0197(6) 0.0171(7) 0.0182(5) -0.0002(5) -0.0015(4) -0.0062(5) C14 0.0151(5) 0.0130(6) 0.0135(5) 0.0006(4) 0.0005(4) 0.0006(5) C15 0.0162(5) 0.0145(7) 0.0156(5) -0.0009(4) 0.0004(4) 0.0021(5) C16 0.0154(5) 0.0164(7) 0.0153(5) 0.0001(5) -0.0002(4) 0.0037(5) C17 0.0182(6) 0.0181(7) 0.0118(5) -0.0002(4) 0.0016(4) -0.0021(5) C18 0.0252(6) 0.0128(6) 0.0171(5) -0.0012(5) 0.0009(5) 0.0009(5) C19 0.0210(6) 0.0155(7) 0.0176(5) 0.0004(5) -0.0001(5) 0.0041(5) C20 0.0189(6) 0.0239(8) 0.0163(5) 0.0016(5) -0.0029(4) -0.0033(6) C21 0.0137(5) 0.0142(7) 0.0148(5) 0.0010(4) -0.0038(4) 0.0001(5) C22 0.0137(5) 0.0164(6) 0.0147(5) 0.0005(4) -0.0023(4) 0.0003(5) C23 0.0141(5) 0.0137(6) 0.0149(5) 0.0004(5) -0.0009(4) 0.0022(5) C24 0.0185(6) 0.0291(8) 0.0220(6) 0.0004(5) 0.0012(5) 0.0070(6) C25 0.0173(6) 0.0236(7) 0.0183(5) 0.0008(5) -0.0035(4) -0.0052(5) C26 0.0174(6) 0.0235(7) 0.0200(6) 0.0041(5) 0.0007(4) -0.0029(6) C27 0.0173(6) 0.0188(7) 0.0201(5) 0.0023(5) -0.0019(4) 0.0054(5) C28 0.0142(5) 0.0149(6) 0.0123(5) 0.0002(4) -0.0003(4) -0.0009(5) C29 0.0208(6) 0.0139(7) 0.0176(5) 0.0006(5) -0.0022(4) 0.0000(5) C30 0.0212(6) 0.0154(7) 0.0188(6) -0.0005(5) -0.0041(5) -0.0042(5) C31 0.0161(5) 0.0210(7) 0.0168(5) 0.0016(5) -0.0043(4) 0.0008(5) C32 0.0199(6) 0.0136(6) 0.0208(5) 0.0027(5) -0.0045(4) 0.0005(5) C33 0.0184(6) 0.0150(6) 0.0178(5) -0.0001(5) -0.0038(4) -0.0012(5) C34 0.0157(5) 0.0146(6) 0.0127(5) -0.0002(4) 0.0013(4) 0.0012(5) C35 0.0182(6) 0.0128(6) 0.0149(5) -0.0007(4) 0.0001(4) 0.0014(5) C36 0.0158(5) 0.0159(7) 0.0158(5) -0.0001(5) 0.0001(4) 0.0031(5) C37 0.0163(5) 0.0178(6) 0.0126(5) -0.0005(4) 0.0006(4) -0.0025(5) C38 0.0230(6) 0.0128(6) 0.0179(5) -0.0025(5) 0.0007(5) 0.0001(5) C39 0.0203(6) 0.0134(7) 0.0166(5) 0.0010(5) 0.0002(4) 0.0049(5) C40 0.0194(6) 0.0244(8) 0.0197(6) 0.0028(5) -0.0040(5) -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 C1 1.2110(19) . ? O2 C11 1.3784(15) . ? O2 H2A 0.82(2) . ? O3 C17 1.3703(15) . ? O3 C20 1.4286(17) . ? O4 C21 1.2176(18) . ? O5 C31 1.3685(15) . ? O5 H5A 0.84(2) . ? O6 C37 1.3682(15) . ? O6 C40 1.4303(17) . ? O7 H7D 0.949(19) . ? O7 H7E 0.88(2) . ? C1 C3 1.5490(17) . ? C1 C2 1.5491(18) . ? C2 C4 1.5369(19) . ? C2 C8 1.5377(17) . ? C2 C5 1.5385(19) . ? C3 C14 1.5373(17) . ? C3 C6 1.5393(18) . ? C3 C7 1.5408(19) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C5 H5D 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.391(2) . ? C8 C9 1.4036(18) . ? C9 C10 1.3877(17) . ? C9 H9A 0.9500 . ? C10 C11 1.389(2) . ? C10 H10A 0.9500 . ? C11 C12 1.3923(18) . ? C12 C13 1.3894(17) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.3943(17) . ? C14 C19 1.4011(18) . ? C15 C16 1.3921(17) . ? C15 H15A 0.9500 . ? C16 C17 1.3908(19) . ? C16 H16A 0.9500 . ? C17 C18 1.3954(19) . ? C18 C19 1.3920(18) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C23 1.5470(17) . ? C21 C22 1.5480(17) . ? C22 C25 1.5272(19) . ? C22 C28 1.5368(16) . ? C22 C24 1.5477(18) . ? C23 C34 1.5309(17) . ? C23 C27 1.5363(18) . ? C23 C26 1.5387(18) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.3952(18) . ? C28 C33 1.4016(19) . ? C29 C30 1.3804(18) . ? C29 H29A 0.9500 . ? C30 C31 1.391(2) . ? C30 H30A 0.9500 . ? C31 C32 1.3893(19) . ? C32 C33 1.3946(17) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 C35 1.3954(17) . ? C34 C39 1.3999(18) . ? C35 C36 1.3914(17) . ? C35 H35A 0.9500 . ? C36 C37 1.3980(19) . ? C36 H36A 0.9500 . ? C37 C38 1.3922(19) . ? C38 C39 1.3860(17) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? 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 C11 O2 H2A 114.4(14) . . ? C17 O3 C20 116.17(11) . . ? C31 O5 H5A 111.0(14) . . ? C37 O6 C40 116.63(11) . . ? H7D O7 H7E 109.6(19) . . ? O1 C1 C3 118.82(12) . . ? O1 C1 C2 119.08(12) . . ? C3 C1 C2 122.10(12) . . ? C4 C2 C8 108.28(10) . . ? C4 C2 C5 106.94(10) . . ? C8 C2 C5 113.08(12) . . ? C4 C2 C1 108.50(12) . . ? C8 C2 C1 107.15(9) . . ? C5 C2 C1 112.75(10) . . ? C14 C3 C6 113.08(11) . . ? C14 C3 C7 108.15(10) . . ? C6 C3 C7 107.07(11) . . ? C14 C3 C1 107.74(9) . . ? C6 C3 C1 112.31(10) . . ? C7 C3 C1 108.33(11) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C2 C5 H5D 109.5 . . ? H5B C5 H5D 109.5 . . ? H5C C5 H5D 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 117.68(11) . . ? C13 C8 C2 123.33(12) . . ? C9 C8 C2 118.94(12) . . ? C10 C9 C8 121.39(13) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C11 119.61(12) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? O2 C11 C10 121.67(12) . . ? O2 C11 C12 118.16(12) . . ? C10 C11 C12 120.15(11) . . ? C13 C12 C11 119.44(13) . . ? C13 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? C12 C13 C8 121.72(12) . . ? C12 C13 H13A 119.1 . . ? C8 C13 H13A 119.1 . . ? C15 C14 C19 117.57(11) . . ? C15 C14 C3 119.45(12) . . ? C19 C14 C3 122.91(11) . . ? C16 C15 C14 121.98(13) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C17 C16 C15 119.57(12) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? O3 C17 C16 124.57(12) . . ? O3 C17 C18 115.80(12) . . ? C16 C17 C18 119.62(12) . . ? C19 C18 C17 120.08(13) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C18 C19 C14 121.18(12) . . ? C18 C19 H19A 119.4 . . ? C14 C19 H19A 119.4 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 C21 C23 119.39(12) . . ? O4 C21 C22 118.73(12) . . ? C23 C21 C22 121.87(11) . . ? C25 C22 C28 112.89(11) . . ? C25 C22 C24 106.85(10) . . ? C28 C22 C24 109.13(10) . . ? C25 C22 C21 114.19(10) . . ? C28 C22 C21 105.79(9) . . ? C24 C22 C21 107.84(11) . . ? C34 C23 C27 113.89(11) . . ? C34 C23 C26 108.42(9) . . ? C27 C23 C26 107.10(10) . . ? C34 C23 C21 107.23(9) . . ? C27 C23 C21 111.78(10) . . ? C26 C23 C21 108.25(11) . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 117.29(11) . . ? C29 C28 C22 119.86(12) . . ? C33 C28 C22 122.85(11) . . ? C30 C29 C28 121.98(13) . . ? C30 C29 H29A 119.0 . . ? C28 C29 H29A 119.0 . . ? C29 C30 C31 119.99(13) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? O5 C31 C32 122.79(13) . . ? O5 C31 C30 117.66(12) . . ? C32 C31 C30 119.55(11) . . ? C31 C32 C33 119.88(13) . . ? C31 C32 H32A 120.1 . . ? C33 C32 H32A 120.1 . . ? C32 C33 C28 121.29(12) . . ? C32 C33 H33A 119.4 . . ? C28 C33 H33A 119.4 . . ? C35 C34 C39 117.25(11) . . ? C35 C34 C23 119.65(12) . . ? C39 C34 C23 123.06(11) . . ? C36 C35 C34 122.22(13) . . ? C36 C35 H35A 118.9 . . ? C34 C35 H35A 118.9 . . ? C35 C36 C37 119.30(12) . . ? C35 C36 H36A 120.4 . . ? C37 C36 H36A 120.4 . . ? O6 C37 C38 116.41(13) . . ? O6 C37 C36 124.17(12) . . ? C38 C37 C36 119.43(11) . . ? C39 C38 C37 120.34(13) . . ? C39 C38 H38A 119.8 . . ? C37 C38 H38A 119.8 . . ? C38 C39 C34 121.45(12) . . ? C38 C39 H39A 119.3 . . ? C34 C39 H39A 119.3 . . ? O6 C40 H40A 109.5 . . ? O6 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O6 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C4 -20.44(16) . . . . ? C3 C1 C2 C4 160.07(11) . . . . ? O1 C1 C2 C8 96.26(14) . . . . ? C3 C1 C2 C8 -83.23(13) . . . . ? O1 C1 C2 C5 -138.70(13) . . . . ? C3 C1 C2 C5 41.81(15) . . . . ? O1 C1 C3 C14 100.32(14) . . . . ? C2 C1 C3 C14 -80.19(13) . . . . ? O1 C1 C3 C6 -134.49(13) . . . . ? C2 C1 C3 C6 44.99(15) . . . . ? O1 C1 C3 C7 -16.45(16) . . . . ? C2 C1 C3 C7 163.04(10) . . . . ? C4 C2 C8 C13 -113.49(14) . . . . ? C5 C2 C8 C13 4.82(16) . . . . ? C1 C2 C8 C13 129.67(13) . . . . ? C4 C2 C8 C9 63.69(14) . . . . ? C5 C2 C8 C9 -178.00(10) . . . . ? C1 C2 C8 C9 -53.16(14) . . . . ? C13 C8 C9 C10 0.64(18) . . . . ? C2 C8 C9 C10 -176.70(11) . . . . ? C8 C9 C10 C11 -0.21(19) . . . . ? C9 C10 C11 O2 178.33(11) . . . . ? C9 C10 C11 C12 -0.36(19) . . . . ? O2 C11 C12 C13 -178.25(11) . . . . ? C10 C11 C12 C13 0.48(19) . . . . ? C11 C12 C13 C8 -0.03(19) . . . . ? C9 C8 C13 C12 -0.52(19) . . . . ? C2 C8 C13 C12 176.69(11) . . . . ? C6 C3 C14 C15 -173.95(11) . . . . ? C7 C3 C14 C15 67.67(14) . . . . ? C1 C3 C14 C15 -49.23(14) . . . . ? C6 C3 C14 C19 9.25(16) . . . . ? C7 C3 C14 C19 -109.13(14) . . . . ? C1 C3 C14 C19 133.97(12) . . . . ? C19 C14 C15 C16 0.34(18) . . . . ? C3 C14 C15 C16 -176.63(10) . . . . ? C14 C15 C16 C17 0.24(18) . . . . ? C20 O3 C17 C16 -0.06(16) . . . . ? C20 O3 C17 C18 179.95(10) . . . . ? C15 C16 C17 O3 179.82(11) . . . . ? C15 C16 C17 C18 -0.19(18) . . . . ? O3 C17 C18 C19 179.55(11) . . . . ? C16 C17 C18 C19 -0.43(18) . . . . ? C17 C18 C19 C14 1.03(19) . . . . ? C15 C14 C19 C18 -0.97(18) . . . . ? C3 C14 C19 C18 175.89(11) . . . . ? O4 C21 C22 C25 143.20(12) . . . . ? C23 C21 C22 C25 -37.57(15) . . . . ? O4 C21 C22 C28 -92.04(14) . . . . ? C23 C21 C22 C28 87.18(13) . . . . ? O4 C21 C22 C24 24.62(15) . . . . ? C23 C21 C22 C24 -156.16(10) . . . . ? O4 C21 C23 C34 -104.10(13) . . . . ? C22 C21 C23 C34 76.68(13) . . . . ? O4 C21 C23 C27 130.41(13) . . . . ? C22 C21 C23 C27 -48.81(15) . . . . ? O4 C21 C23 C26 12.68(16) . . . . ? C22 C21 C23 C26 -166.54(10) . . . . ? C25 C22 C28 C29 -177.35(11) . . . . ? C24 C22 C28 C29 -58.69(14) . . . . ? C21 C22 C28 C29 57.09(14) . . . . ? C25 C22 C28 C33 2.47(16) . . . . ? C24 C22 C28 C33 121.12(13) . . . . ? C21 C22 C28 C33 -123.09(12) . . . . ? C33 C28 C29 C30 0.27(18) . . . . ? C22 C28 C29 C30 -179.91(11) . . . . ? C28 C29 C30 C31 0.77(19) . . . . ? C29 C30 C31 O5 178.49(11) . . . . ? C29 C30 C31 C32 -1.7(2) . . . . ? O5 C31 C32 C33 -178.63(12) . . . . ? C30 C31 C32 C33 1.56(19) . . . . ? C31 C32 C33 C28 -0.51(19) . . . . ? C29 C28 C33 C32 -0.40(18) . . . . ? C22 C28 C33 C32 179.78(11) . . . . ? C27 C23 C34 C35 172.65(10) . . . . ? C26 C23 C34 C35 -68.24(14) . . . . ? C21 C23 C34 C35 48.43(14) . . . . ? C27 C23 C34 C39 -9.44(16) . . . . ? C26 C23 C34 C39 109.67(13) . . . . ? C21 C23 C34 C39 -133.66(12) . . . . ? C39 C34 C35 C36 -0.81(17) . . . . ? C23 C34 C35 C36 177.22(10) . . . . ? C34 C35 C36 C37 -0.26(18) . . . . ? C40 O6 C37 C38 -178.83(11) . . . . ? C40 O6 C37 C36 1.29(17) . . . . ? C35 C36 C37 O6 -179.39(11) . . . . ? C35 C36 C37 C38 0.73(17) . . . . ? O6 C37 C38 C39 -179.99(11) . . . . ? C36 C37 C38 C39 -0.10(18) . . . . ? C37 C38 C39 C34 -1.03(18) . . . . ? C35 C34 C39 C38 1.46(18) . . . . ? C23 C34 C39 C38 -176.50(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.337 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.042 # Attachment '630995-2a1.cif' #============================================================ data_MonoHO-biscyclohexanone _database_code_depnum_ccdc_archive 'CCDC 630994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "MonoHOTMK, 4,4'-biscyclohexanone" _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 O3, 0.5(C12 H18 O2)' _chemical_formula_sum 'C26 H33 O4' _chemical_formula_weight 409.52 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 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 6.2893(2) _cell_length_b 7.9701(2) _cell_length_c 43.7044(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.9470(10) _cell_angle_gamma 90.00 _cell_volume 2187.84(10) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 7288 _cell_measurement_theta_min 2.721 _cell_measurement_theta_max 28.261 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'empirical SADABS' _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'Blessing, R. (1995) Acta Crystallogr., A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29627 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5390 _reflns_number_gt 4936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0551P)^2^+0.9835P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5390 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 -0.36875(13) 0.28880(11) 0.15275(2) 0.02428(19) Uani 1 1 d . . . O2 O 0.30237(13) -0.17530(11) 0.253407(18) 0.02243(18) Uani 1 1 d . . . O3 O 0.07201(15) 0.79132(12) 0.047377(19) 0.0262(2) Uani 1 1 d . . . H3A H 0.195(3) 0.838(3) 0.0477(4) 0.047(5) Uiso 1 1 d . . . O4 O 0.44697(14) -0.03878(11) 0.04771(2) 0.0282(2) Uani 1 1 d . . . C1 C -0.17569(17) 0.28736(13) 0.15272(2) 0.0154(2) Uani 1 1 d . . . C2 C -0.06163(16) 0.12286(13) 0.14398(2) 0.0148(2) Uani 1 1 d . . . C3 C -0.05193(16) 0.45155(13) 0.16032(2) 0.0149(2) Uani 1 1 d . . . C4 C 0.09702(18) 0.15499(14) 0.11890(2) 0.0183(2) Uani 1 1 d . . . H4C H 0.146(2) 0.0470(19) 0.1109(3) 0.022(3) Uiso 1 1 d . . . H4B H 0.222(2) 0.220(2) 0.1259(3) 0.024(4) Uiso 1 1 d . . . H4A H 0.025(2) 0.2157(18) 0.1015(3) 0.021(3) Uiso 1 1 d . . . C5 C -0.23018(19) -0.00273(15) 0.13140(3) 0.0206(2) Uani 1 1 d . . . H5C H -0.305(3) 0.041(2) 0.1125(4) 0.030(4) Uiso 1 1 d . . . H5B H -0.155(2) -0.107(2) 0.1260(4) 0.028(4) Uiso 1 1 d . . . H5A H -0.334(2) -0.0287(19) 0.1470(3) 0.024(4) Uiso 1 1 d . . . C6 C -0.19701(19) 0.56911(14) 0.17808(3) 0.0198(2) Uani 1 1 d . . . H6C H -0.237(2) 0.517(2) 0.1973(4) 0.028(4) Uiso 1 1 d . . . H6B H -0.333(2) 0.5950(19) 0.1657(3) 0.023(4) Uiso 1 1 d . . . H6A H -0.120(3) 0.675(2) 0.1823(4) 0.030(4) Uiso 1 1 d . . . C7 C 0.15154(18) 0.42291(14) 0.18067(3) 0.0183(2) Uani 1 1 d . . . H7C H 0.222(2) 0.533(2) 0.1857(3) 0.024(4) Uiso 1 1 d . . . H7B H 0.260(2) 0.352(2) 0.1711(3) 0.027(4) Uiso 1 1 d . . . H7A H 0.113(2) 0.371(2) 0.2003(4) 0.028(4) Uiso 1 1 d . . . C8 C 0.04446(16) 0.04496(12) 0.17299(2) 0.0146(2) Uani 1 1 d . . . C9 C 0.23708(17) -0.03992(13) 0.17263(2) 0.0171(2) Uani 1 1 d . . . H9A H 0.311(2) -0.0452(19) 0.1538(3) 0.023(4) Uiso 1 1 d . . . C10 C 0.32823(17) -0.11747(13) 0.19877(3) 0.0176(2) Uani 1 1 d . . . H10A H 0.462(3) -0.174(2) 0.1978(4) 0.028(4) Uiso 1 1 d . . . C11 C 0.22559(17) -0.10884(13) 0.22608(2) 0.0171(2) Uani 1 1 d . . . C12 C 0.03139(18) -0.02429(15) 0.22706(3) 0.0198(2) Uani 1 1 d . . . H12A H -0.051(2) -0.0227(17) 0.2501(3) 0.015(3) Uiso 1 1 d . . . C13 C -0.05775(17) 0.04971(14) 0.20070(2) 0.0182(2) Uani 1 1 d . . . H13A H -0.192(2) 0.1057(19) 0.2017(3) 0.025(4) Uiso 1 1 d . . . C14 C -0.00854(17) 0.53499(12) 0.12952(2) 0.0147(2) Uani 1 1 d . . . C15 C 0.19169(17) 0.59500(14) 0.12260(2) 0.0175(2) Uani 1 1 d . . . H15A H 0.311(2) 0.5785(18) 0.1373(3) 0.019(3) Uiso 1 1 d . . . C16 C 0.22285(18) 0.67989(14) 0.09527(3) 0.0190(2) Uani 1 1 d . . . H16A H 0.361(2) 0.7241(19) 0.0916(3) 0.026(4) Uiso 1 1 d . . . C17 C 0.05278(18) 0.70606(14) 0.07419(2) 0.0186(2) Uani 1 1 d . . . C18 C -0.14778(18) 0.64407(14) 0.08044(2) 0.0186(2) Uani 1 1 d . . . H18A H -0.267(2) 0.6687(19) 0.0660(3) 0.023(4) Uiso 1 1 d . . . C19 C -0.17659(17) 0.56011(13) 0.10773(2) 0.0164(2) Uani 1 1 d . . . H19A H -0.316(2) 0.5204(18) 0.1120(3) 0.018(3) Uiso 1 1 d . . . C20 C 0.5006(2) -0.26069(17) 0.25343(3) 0.0262(3) Uani 1 1 d . . . H20B H 0.491(3) -0.359(2) 0.2399(4) 0.032(4) Uiso 1 1 d . . . H20A H 0.615(2) -0.186(2) 0.2463(4) 0.028(4) Uiso 1 1 d . . . H20C H 0.534(3) -0.295(2) 0.2746(4) 0.033(4) Uiso 1 1 d . . . C21 C 0.44536(19) 0.11404(16) 0.04469(3) 0.0241(2) Uani 1 1 d . . . C22 C 0.6427(2) 0.21820(16) 0.05010(3) 0.0248(2) Uani 1 1 d . . . H22B H 0.766(3) 0.138(2) 0.0538(4) 0.033(4) Uiso 1 1 d . . . H22A H 0.621(3) 0.290(2) 0.0692(4) 0.034(4) Uiso 1 1 d . . . C23 C 0.67769(18) 0.33731(15) 0.02314(3) 0.0195(2) Uani 1 1 d . . . H23B H 0.716(2) 0.270(2) 0.0051(4) 0.026(4) Uiso 1 1 d . . . H23A H 0.800(3) 0.408(2) 0.0282(4) 0.029(4) Uiso 1 1 d . . . C24 C 0.48085(17) 0.44241(14) 0.01377(2) 0.0196(2) Uani 1 1 d . . . H24A H 0.448(2) 0.518(2) 0.0322(4) 0.027(4) Uiso 1 1 d . . . C25 C 0.29098(18) 0.32494(16) 0.00742(3) 0.0232(2) Uani 1 1 d . . . H25B H 0.161(3) 0.389(2) 0.0025(4) 0.031(4) Uiso 1 1 d . . . H25A H 0.323(3) 0.249(2) -0.0103(4) 0.036(4) Uiso 1 1 d . . . C26 C 0.2484(2) 0.21098(18) 0.03481(3) 0.0290(3) Uani 1 1 d . . . H26A H 0.129(3) 0.124(2) 0.0286(4) 0.039(4) Uiso 1 1 d . . . H26B H 0.214(3) 0.288(2) 0.0525(4) 0.041(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 0.0141(4) 0.0204(4) 0.0384(5) 0.0010(3) 0.0018(3) 0.0001(3) O2 0.0225(4) 0.0252(4) 0.0194(4) 0.0065(3) -0.0006(3) 0.0020(3) O3 0.0274(5) 0.0339(5) 0.0172(4) 0.0075(3) -0.0010(3) -0.0098(4) O4 0.0263(5) 0.0273(5) 0.0307(5) 0.0101(4) 0.0002(4) -0.0043(3) C1 0.0158(5) 0.0151(5) 0.0152(5) 0.0029(4) 0.0008(4) 0.0001(4) C2 0.0154(5) 0.0144(5) 0.0146(4) 0.0004(4) 0.0012(4) 0.0001(4) C3 0.0150(5) 0.0143(5) 0.0155(5) 0.0008(4) 0.0006(4) 0.0000(4) C4 0.0207(5) 0.0185(5) 0.0160(5) 0.0005(4) 0.0040(4) 0.0007(4) C5 0.0221(5) 0.0180(5) 0.0213(5) -0.0007(4) -0.0021(4) -0.0037(4) C6 0.0240(6) 0.0176(5) 0.0182(5) -0.0011(4) 0.0044(4) 0.0022(4) C7 0.0182(5) 0.0180(5) 0.0185(5) 0.0006(4) -0.0019(4) -0.0011(4) C8 0.0154(5) 0.0121(4) 0.0163(5) 0.0001(4) 0.0011(4) -0.0012(4) C9 0.0172(5) 0.0174(5) 0.0169(5) -0.0015(4) 0.0031(4) 0.0004(4) C10 0.0162(5) 0.0157(5) 0.0209(5) -0.0009(4) 0.0005(4) 0.0017(4) C11 0.0187(5) 0.0140(5) 0.0182(5) 0.0024(4) -0.0016(4) -0.0024(4) C12 0.0200(5) 0.0222(5) 0.0174(5) 0.0027(4) 0.0039(4) 0.0004(4) C13 0.0166(5) 0.0189(5) 0.0193(5) 0.0015(4) 0.0035(4) 0.0025(4) C14 0.0173(5) 0.0117(4) 0.0152(5) -0.0003(4) 0.0013(4) -0.0001(4) C15 0.0159(5) 0.0182(5) 0.0183(5) 0.0007(4) -0.0009(4) -0.0008(4) C16 0.0178(5) 0.0196(5) 0.0199(5) 0.0007(4) 0.0024(4) -0.0038(4) C17 0.0236(5) 0.0175(5) 0.0146(5) 0.0002(4) 0.0013(4) -0.0030(4) C18 0.0197(5) 0.0200(5) 0.0158(5) -0.0007(4) -0.0024(4) -0.0020(4) C19 0.0163(5) 0.0150(5) 0.0178(5) -0.0012(4) 0.0009(4) -0.0019(4) C20 0.0255(6) 0.0263(6) 0.0264(6) 0.0066(5) -0.0031(5) 0.0027(5) C21 0.0233(6) 0.0295(6) 0.0194(5) 0.0078(4) 0.0014(4) -0.0040(5) C22 0.0232(6) 0.0281(6) 0.0225(6) 0.0062(5) -0.0039(4) -0.0037(5) C23 0.0163(5) 0.0231(5) 0.0188(5) 0.0036(4) -0.0019(4) -0.0029(4) C24 0.0170(5) 0.0229(5) 0.0187(5) 0.0036(4) -0.0001(4) -0.0023(4) C25 0.0160(5) 0.0275(6) 0.0257(6) 0.0088(5) -0.0031(4) -0.0045(4) C26 0.0200(6) 0.0327(7) 0.0342(7) 0.0127(5) 0.0026(5) -0.0038(5) _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 C1 1.2143(13) . ? O2 C11 1.3716(13) . ? O2 C20 1.4202(15) . ? O3 C17 1.3653(13) . ? O3 H3A 0.86(2) . ? O4 C21 1.2252(16) . ? C1 C3 1.5499(14) . ? C1 C2 1.5516(14) . ? C2 C8 1.5333(14) . ? C2 C5 1.5389(15) . ? C2 C4 1.5413(14) . ? C3 C7 1.5373(14) . ? C3 C14 1.5386(14) . ? C3 C6 1.5446(15) . ? C4 H4C 0.985(15) . ? C4 H4B 0.975(16) . ? C4 H4A 0.990(15) . ? C5 H5C 0.994(17) . ? C5 H5B 0.991(16) . ? C5 H5A 0.990(16) . ? C6 H6C 0.981(16) . ? C6 H6B 1.010(15) . ? C6 H6A 0.988(17) . ? C7 H7C 1.000(16) . ? C7 H7B 0.993(16) . ? C7 H7A 0.993(16) . ? C8 C9 1.3883(15) . ? C8 C13 1.4004(15) . ? C9 C10 1.3961(15) . ? C9 H9A 0.967(15) . ? C10 C11 1.3873(15) . ? C10 H10A 0.955(16) . ? C11 C12 1.3975(15) . ? C12 C13 1.3868(15) . ? C12 H12A 1.155(13) . ? C13 H13A 0.960(16) . ? C14 C15 1.3948(15) . ? C14 C19 1.4002(15) . ? C15 C16 1.3951(15) . ? C15 H15A 0.971(14) . ? C16 C17 1.3911(16) . ? C16 H16A 0.957(16) . ? C17 C18 1.3947(16) . ? C18 C19 1.3876(15) . ? C18 H18A 0.975(15) . ? C19 H19A 0.961(14) . ? C20 H20B 0.979(17) . ? C20 H20A 0.995(16) . ? C20 H20C 0.978(17) . ? C21 C22 1.5020(17) . ? C21 C26 1.5043(17) . ? C22 C23 1.5378(16) . ? C22 H22B 1.008(17) . ? C22 H22A 1.030(17) . ? C23 C24 1.5329(15) . ? C23 H23B 0.994(16) . ? C23 H23A 0.973(16) . ? C24 C25 1.5315(15) . ? C24 C24 1.543(2) 3_665 ? C24 H24A 1.034(16) . ? C25 C26 1.5373(16) . ? C25 H25B 0.975(16) . ? C25 H25A 1.010(18) . ? C26 H26A 1.049(18) . ? C26 H26B 1.020(19) . ? 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 C11 O2 C20 117.09(9) . . ? C17 O3 H3A 108.7(13) . . ? O1 C1 C3 118.88(9) . . ? O1 C1 C2 118.90(10) . . ? C3 C1 C2 122.19(9) . . ? C8 C2 C5 107.13(8) . . ? C8 C2 C4 112.66(9) . . ? C5 C2 C4 108.25(9) . . ? C8 C2 C1 109.00(8) . . ? C5 C2 C1 108.59(9) . . ? C4 C2 C1 111.05(8) . . ? C7 C3 C14 112.99(9) . . ? C7 C3 C6 107.17(9) . . ? C14 C3 C6 108.26(8) . . ? C7 C3 C1 113.12(9) . . ? C14 C3 C1 106.68(8) . . ? C6 C3 C1 108.47(9) . . ? C2 C4 H4C 109.5(9) . . ? C2 C4 H4B 113.8(9) . . ? H4C C4 H4B 108.5(12) . . ? C2 C4 H4A 109.8(8) . . ? H4C C4 H4A 107.0(12) . . ? H4B C4 H4A 108.1(12) . . ? C2 C5 H5C 110.9(9) . . ? C2 C5 H5B 107.4(9) . . ? H5C C5 H5B 107.9(13) . . ? C2 C5 H5A 111.0(9) . . ? H5C C5 H5A 110.2(13) . . ? H5B C5 H5A 109.2(13) . . ? C3 C6 H6C 111.1(9) . . ? C3 C6 H6B 111.3(9) . . ? H6C C6 H6B 107.2(12) . . ? C3 C6 H6A 108.5(9) . . ? H6C C6 H6A 110.1(13) . . ? H6B C6 H6A 108.7(13) . . ? C3 C7 H7C 110.0(9) . . ? C3 C7 H7B 114.2(9) . . ? H7C C7 H7B 106.5(12) . . ? C3 C7 H7A 109.2(9) . . ? H7C C7 H7A 107.4(13) . . ? H7B C7 H7A 109.3(13) . . ? C9 C8 C13 117.56(10) . . ? C9 C8 C2 122.05(9) . . ? C13 C8 C2 120.29(9) . . ? C8 C9 C10 121.88(10) . . ? C8 C9 H9A 119.3(9) . . ? C10 C9 H9A 118.9(9) . . ? C11 C10 C9 119.50(10) . . ? C11 C10 H10A 120.7(9) . . ? C9 C10 H10A 119.8(9) . . ? O2 C11 C10 124.85(10) . . ? O2 C11 C12 115.38(10) . . ? C10 C11 C12 119.76(10) . . ? C13 C12 C11 119.74(10) . . ? C13 C12 H12A 122.6(7) . . ? C11 C12 H12A 117.6(7) . . ? C12 C13 C8 121.53(10) . . ? C12 C13 H13A 118.6(9) . . ? C8 C13 H13A 119.9(9) . . ? C15 C14 C19 117.51(10) . . ? C15 C14 C3 122.73(9) . . ? C19 C14 C3 119.69(9) . . ? C14 C15 C16 121.34(10) . . ? C14 C15 H15A 119.0(8) . . ? C16 C15 H15A 119.6(8) . . ? C17 C16 C15 120.17(10) . . ? C17 C16 H16A 120.4(9) . . ? C15 C16 H16A 119.4(9) . . ? O3 C17 C16 122.96(10) . . ? O3 C17 C18 117.73(10) . . ? C16 C17 C18 119.31(10) . . ? C19 C18 C17 119.90(10) . . ? C19 C18 H18A 121.4(9) . . ? C17 C18 H18A 118.5(9) . . ? C18 C19 C14 121.75(10) . . ? C18 C19 H19A 119.1(9) . . ? C14 C19 H19A 119.1(8) . . ? O2 C20 H20B 110.7(10) . . ? O2 C20 H20A 111.2(9) . . ? H20B C20 H20A 108.2(13) . . ? O2 C20 H20C 106.5(10) . . ? H20B C20 H20C 110.3(14) . . ? H20A C20 H20C 109.9(13) . . ? O4 C21 C22 122.03(11) . . ? O4 C21 C26 122.93(11) . . ? C22 C21 C26 115.03(11) . . ? C21 C22 C23 111.71(9) . . ? C21 C22 H22B 107.3(9) . . ? C23 C22 H22B 111.9(9) . . ? C21 C22 H22A 107.0(9) . . ? C23 C22 H22A 107.9(9) . . ? H22B C22 H22A 110.9(13) . . ? C24 C23 C22 113.38(9) . . ? C24 C23 H23B 107.9(9) . . ? C22 C23 H23B 109.0(9) . . ? C24 C23 H23A 111.3(9) . . ? C22 C23 H23A 109.1(9) . . ? H23B C23 H23A 105.9(13) . . ? C25 C24 C23 109.01(9) . . ? C25 C24 C24 111.95(11) . 3_665 ? C23 C24 C24 112.17(11) . 3_665 ? C25 C24 H24A 108.0(9) . . ? C23 C24 H24A 107.6(9) . . ? C24 C24 H24A 107.9(9) 3_665 . ? C24 C25 C26 112.67(10) . . ? C24 C25 H25B 110.9(10) . . ? C26 C25 H25B 107.6(10) . . ? C24 C25 H25A 108.8(10) . . ? C26 C25 H25A 107.0(10) . . ? H25B C25 H25A 109.8(13) . . ? C21 C26 C25 110.67(10) . . ? C21 C26 H26A 107.8(10) . . ? C25 C26 H26A 109.8(10) . . ? C21 C26 H26B 107.1(10) . . ? C25 C26 H26B 106.8(10) . . ? H26A C26 H26B 114.6(14) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.414 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.044 # Attachment '630996-1a.cif' #============================================================ data_scale _database_code_depnum_ccdc_archive 'CCDC 630995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common HOTMK-biscyclohexanone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H40 O5' _chemical_formula_weight 492.63 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 7.74590(10) _cell_length_b 11.0192(2) _cell_length_c 16.6519(3) _cell_angle_alpha 109.2590(10) _cell_angle_beta 92.6450(10) _cell_angle_gamma 90.7540(10) _cell_volume 1339.72(4) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 4447 _cell_measurement_theta_min 2.634 _cell_measurement_theta_max 26.359 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.085 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'empirical SADABS' _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'Blessing, R. (1995) Acta Crystallogr., A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14589 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5489 _reflns_number_gt 4321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0466P)^2^+0.3199P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5489 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.002 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 0.20888(12) 0.96363(9) 0.02687(6) 0.0216(2) Uani 1 1 d . . . O2 O 0.73826(12) 0.77366(10) 0.30255(6) 0.0217(2) Uani 1 1 d . . . H2A H 0.798(2) 0.8478(17) 0.3199(11) 0.036(5) Uiso 1 1 d . . . O3 O -0.24061(12) 0.49997(10) -0.30473(6) 0.0231(2) Uani 1 1 d . . . H3A H -0.310(3) 0.5573(19) -0.3177(12) 0.048(6) Uiso 1 1 d . . . O4 O -0.05868(12) 0.99610(9) 0.36184(6) 0.0229(2) Uani 1 1 d . . . O5 O 0.45386(12) 0.33250(10) 0.34748(6) 0.0270(2) Uani 1 1 d . . . C1 C 0.22141(16) 0.84989(12) 0.01652(8) 0.0156(3) Uani 1 1 d . . . C2 C 0.30463(16) 0.76180(13) -0.06442(8) 0.0176(3) Uani 1 1 d . . . C3 C 0.15434(16) 0.79676(12) 0.08507(8) 0.0164(3) Uani 1 1 d . . . C4 C 0.43853(18) 0.67280(14) -0.04435(9) 0.0215(3) Uani 1 1 d . . . H4C H 0.3890(19) 0.6098(15) -0.0201(10) 0.023(4) Uiso 1 1 d . . . H4B H 0.496(2) 0.6235(16) -0.0971(11) 0.031(4) Uiso 1 1 d . . . H4A H 0.529(2) 0.7252(15) -0.0046(10) 0.029(4) Uiso 1 1 d . . . C5 C 0.39921(19) 0.84747(15) -0.10624(9) 0.0248(3) Uani 1 1 d . . . H5C H 0.497(2) 0.8957(15) -0.0673(10) 0.032(4) Uiso 1 1 d . . . H5B H 0.321(2) 0.9117(16) -0.1197(10) 0.030(4) Uiso 1 1 d . . . H5A H 0.449(2) 0.7900(15) -0.1610(11) 0.030(4) Uiso 1 1 d . . . C6 C 0.03122(18) 0.89429(14) 0.14021(9) 0.0221(3) Uani 1 1 d . . . H6C H -0.014(2) 0.8587(15) 0.1842(10) 0.031(4) Uiso 1 1 d . . . H6B H 0.091(2) 0.9805(15) 0.1707(10) 0.025(4) Uiso 1 1 d . . . H6A H -0.066(2) 0.9080(15) 0.1054(10) 0.029(4) Uiso 1 1 d . . . C7 C 0.05206(18) 0.66852(14) 0.04647(9) 0.0199(3) Uani 1 1 d . . . H7C H 0.121(2) 0.5981(15) 0.0115(10) 0.024(4) Uiso 1 1 d . . . H7B H 0.0066(19) 0.6425(14) 0.0936(10) 0.025(4) Uiso 1 1 d . . . H7A H -0.048(2) 0.6792(14) 0.0099(10) 0.026(4) Uiso 1 1 d . . . C8 C 0.15534(16) 0.68867(12) -0.12637(8) 0.0167(3) Uani 1 1 d . . . C9 C 0.01999(18) 0.75775(13) -0.14655(9) 0.0202(3) Uani 1 1 d . . . H9A H 0.0169(19) 0.8483(15) -0.1203(9) 0.023(4) Uiso 1 1 d . . . C10 C -0.11370(18) 0.69752(13) -0.20508(9) 0.0210(3) Uani 1 1 d . . . H10A H -0.208(2) 0.7479(15) -0.2193(10) 0.026(4) Uiso 1 1 d . . . C11 C -0.11445(16) 0.56475(13) -0.24493(8) 0.0177(3) Uani 1 1 d . . . C12 C 0.01611(17) 0.49379(13) -0.22403(8) 0.0193(3) Uani 1 1 d . . . H12A H 0.0158(19) 0.3995(15) -0.2525(10) 0.027(4) Uiso 1 1 d . . . C13 C 0.14936(17) 0.55578(13) -0.16532(8) 0.0178(3) Uani 1 1 d . . . H13A H 0.2407(19) 0.5065(14) -0.1516(9) 0.020(4) Uiso 1 1 d . . . C14 C 0.31333(16) 0.78720(12) 0.14152(8) 0.0153(3) Uani 1 1 d . . . C15 C 0.34725(17) 0.67858(12) 0.16418(8) 0.0166(3) Uani 1 1 d . . . H15A H 0.2711(18) 0.6028(14) 0.1429(9) 0.018(4) Uiso 1 1 d . . . C16 C 0.48848(17) 0.67559(13) 0.21789(8) 0.0178(3) Uani 1 1 d . . . H16A H 0.5064(19) 0.5971(15) 0.2333(9) 0.023(4) Uiso 1 1 d . . . C17 C 0.60182(16) 0.78113(12) 0.24928(8) 0.0165(3) Uani 1 1 d . . . C18 C 0.57172(17) 0.89050(13) 0.22690(8) 0.0178(3) Uani 1 1 d . . . H18A H 0.649(2) 0.9666(15) 0.2484(10) 0.024(4) Uiso 1 1 d . . . C19 C 0.42869(17) 0.89268(13) 0.17417(8) 0.0166(3) Uani 1 1 d . . . H19A H 0.4116(18) 0.9696(14) 0.1596(9) 0.017(4) Uiso 1 1 d . . . C20 C 0.09750(17) 0.98489(13) 0.37152(8) 0.0179(3) Uani 1 1 d . . . C21 C 0.17610(18) 0.86131(13) 0.37161(9) 0.0199(3) Uani 1 1 d . . . H21B H 0.2342(19) 0.8274(14) 0.3192(10) 0.021(4) Uiso 1 1 d . . . H21A H 0.085(2) 0.7953(15) 0.3698(9) 0.024(4) Uiso 1 1 d . . . C22 C 0.30660(17) 0.88071(13) 0.44757(9) 0.0181(3) Uani 1 1 d . . . H22B H 0.3638(19) 0.7978(14) 0.4393(9) 0.021(4) Uiso 1 1 d . . . H22A H 0.2403(19) 0.8993(14) 0.4999(10) 0.021(4) Uiso 1 1 d . . . C23 C 0.43970(16) 0.99040(12) 0.45998(8) 0.0154(3) Uani 1 1 d . . . H23A H 0.5129(18) 0.9676(13) 0.4105(9) 0.014(3) Uiso 1 1 d . . . C24 C 0.34435(17) 1.11319(13) 0.46398(9) 0.0177(3) Uani 1 1 d . . . H24B H 0.4265(19) 1.1863(14) 0.4698(9) 0.019(4) Uiso 1 1 d . . . H24A H 0.2740(18) 1.1372(13) 0.5150(9) 0.019(4) Uiso 1 1 d . . . C25 C 0.22432(17) 1.09430(13) 0.38432(9) 0.0193(3) Uani 1 1 d . . . H25A H 0.2955(19) 1.0702(14) 0.3337(10) 0.024(4) Uiso 1 1 d . . . H25B H 0.1620(19) 1.1733(14) 0.3877(9) 0.021(4) Uiso 1 1 d . . . C26 C 0.60517(17) 0.36833(13) 0.36652(8) 0.0191(3) Uani 1 1 d . . . C27 C 0.73998(18) 0.27942(13) 0.37943(9) 0.0225(3) Uani 1 1 d . . . H27B H 0.683(2) 0.1982(16) 0.3788(10) 0.028(4) Uiso 1 1 d . . . H27A H 0.815(2) 0.2619(16) 0.3303(11) 0.037(5) Uiso 1 1 d . . . C28 C 0.85285(17) 0.34377(13) 0.46098(9) 0.0192(3) Uani 1 1 d . . . H28B H 0.9391(19) 0.2811(14) 0.4661(9) 0.021(4) Uiso 1 1 d . . . H28A H 0.7780(19) 0.3646(14) 0.5115(9) 0.021(4) Uiso 1 1 d . . . C29 C 0.93860(16) 0.46950(12) 0.46053(8) 0.0158(3) Uani 1 1 d . . . H29A H 1.0060(18) 0.4497(13) 0.4093(9) 0.017(4) Uiso 1 1 d . . . C30 C 0.79550(18) 0.56041(13) 0.45322(9) 0.0208(3) Uani 1 1 d . . . H30B H 0.841(2) 0.6391(16) 0.4471(10) 0.030(4) Uiso 1 1 d . . . H30A H 0.729(2) 0.5837(15) 0.5062(10) 0.027(4) Uiso 1 1 d . . . C31 C 0.66703(18) 0.50247(14) 0.37679(9) 0.0222(3) Uani 1 1 d . . . H31B H 0.568(2) 0.5590(15) 0.3777(10) 0.026(4) Uiso 1 1 d . . . H31A H 0.725(2) 0.4935(15) 0.3237(10) 0.028(4) 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 0.0264(5) 0.0163(5) 0.0225(5) 0.0076(4) -0.0028(4) -0.0008(4) O2 0.0177(5) 0.0230(5) 0.0238(5) 0.0078(4) -0.0072(4) 0.0007(4) O3 0.0194(5) 0.0257(5) 0.0228(5) 0.0072(4) -0.0069(4) -0.0060(4) O4 0.0166(5) 0.0256(5) 0.0231(5) 0.0039(4) -0.0033(4) 0.0021(4) O5 0.0199(5) 0.0310(6) 0.0313(6) 0.0134(5) -0.0080(4) -0.0059(4) C1 0.0131(6) 0.0170(7) 0.0157(6) 0.0051(5) -0.0060(5) -0.0025(5) C2 0.0167(7) 0.0199(7) 0.0156(6) 0.0054(5) -0.0013(5) -0.0027(5) C3 0.0149(6) 0.0177(6) 0.0163(6) 0.0058(5) -0.0023(5) -0.0022(5) C4 0.0157(7) 0.0250(7) 0.0204(7) 0.0033(6) -0.0023(6) 0.0014(6) C5 0.0235(8) 0.0306(8) 0.0205(7) 0.0089(6) 0.0002(6) -0.0082(6) C6 0.0191(7) 0.0266(8) 0.0201(7) 0.0071(6) 0.0000(6) 0.0035(6) C7 0.0185(7) 0.0214(7) 0.0204(7) 0.0085(6) -0.0028(6) -0.0045(6) C8 0.0168(7) 0.0199(7) 0.0137(6) 0.0061(5) 0.0007(5) -0.0020(5) C9 0.0243(7) 0.0161(7) 0.0199(7) 0.0060(6) -0.0023(5) -0.0011(5) C10 0.0198(7) 0.0224(7) 0.0226(7) 0.0104(6) -0.0029(5) 0.0011(6) C11 0.0157(6) 0.0230(7) 0.0151(6) 0.0075(5) -0.0013(5) -0.0048(5) C12 0.0195(7) 0.0180(7) 0.0179(7) 0.0026(6) 0.0008(5) -0.0010(5) C13 0.0154(7) 0.0198(7) 0.0175(6) 0.0051(5) 0.0005(5) 0.0019(5) C14 0.0156(6) 0.0169(6) 0.0132(6) 0.0046(5) 0.0010(5) 0.0010(5) C15 0.0175(7) 0.0150(6) 0.0171(6) 0.0049(5) 0.0018(5) -0.0010(5) C16 0.0193(7) 0.0171(7) 0.0183(7) 0.0072(5) 0.0020(5) 0.0038(5) C17 0.0144(6) 0.0205(7) 0.0132(6) 0.0038(5) 0.0009(5) 0.0035(5) C18 0.0172(7) 0.0171(7) 0.0171(6) 0.0031(5) 0.0005(5) -0.0015(5) C19 0.0198(7) 0.0148(6) 0.0160(6) 0.0063(5) 0.0004(5) 0.0004(5) C20 0.0181(7) 0.0224(7) 0.0098(6) 0.0011(5) -0.0017(5) 0.0013(5) C21 0.0175(7) 0.0179(7) 0.0207(7) 0.0022(6) -0.0037(5) -0.0013(5) C22 0.0175(7) 0.0156(7) 0.0207(7) 0.0057(6) -0.0027(5) -0.0006(5) C23 0.0162(6) 0.0142(6) 0.0149(6) 0.0039(5) 0.0003(5) 0.0002(5) C24 0.0178(7) 0.0159(7) 0.0189(7) 0.0055(5) -0.0025(5) -0.0006(5) C25 0.0194(7) 0.0186(7) 0.0204(7) 0.0075(6) -0.0016(5) 0.0026(5) C26 0.0191(7) 0.0253(7) 0.0120(6) 0.0053(5) -0.0010(5) -0.0023(5) C27 0.0200(7) 0.0185(7) 0.0259(8) 0.0038(6) -0.0035(6) -0.0022(6) C28 0.0166(7) 0.0168(7) 0.0240(7) 0.0067(6) -0.0031(5) -0.0001(5) C29 0.0146(6) 0.0180(7) 0.0154(7) 0.0065(5) 0.0003(5) 0.0000(5) C30 0.0191(7) 0.0162(7) 0.0282(8) 0.0096(6) -0.0053(6) -0.0009(5) C31 0.0180(7) 0.0265(8) 0.0256(8) 0.0144(6) -0.0048(6) -0.0015(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 C1 1.2133(15) . ? O2 C17 1.3692(15) . ? O2 H2A 0.889(19) . ? O3 C11 1.3708(15) . ? O3 H3A 0.91(2) . ? O4 C20 1.2264(16) . ? O5 C26 1.2252(16) . ? C1 C3 1.5502(17) . ? C1 C2 1.5518(18) . ? C2 C4 1.5363(19) . ? C2 C8 1.5388(17) . ? C2 C5 1.5412(19) . ? C3 C6 1.5377(18) . ? C3 C7 1.5368(18) . ? C3 C14 1.5406(17) . ? C4 H4C 0.992(16) . ? C4 H4B 0.995(17) . ? C4 H4A 0.977(17) . ? C5 H5C 0.997(17) . ? C5 H5B 1.013(16) . ? C5 H5A 1.020(16) . ? C6 H6C 1.010(17) . ? C6 H6B 1.013(16) . ? C6 H6A 0.971(16) . ? C7 H7C 0.984(16) . ? C7 H7B 0.997(16) . ? C7 H7A 0.994(16) . ? C8 C13 1.3915(18) . ? C8 C9 1.3959(18) . ? C9 C10 1.3873(19) . ? C9 H9A 0.949(15) . ? C10 C11 1.3928(19) . ? C10 H10A 0.991(16) . ? C11 C12 1.3868(19) . ? C12 C13 1.3912(18) . ? C12 H12A 0.989(16) . ? C13 H13A 0.962(15) . ? C14 C15 1.3932(18) . ? C14 C19 1.3986(18) . ? C15 C16 1.3884(18) . ? C15 H15A 0.972(15) . ? C16 C17 1.3880(19) . ? C16 H16A 0.990(15) . ? C17 C18 1.3934(18) . ? C18 C19 1.3869(18) . ? C18 H18A 0.979(16) . ? C19 H19A 0.965(15) . ? C20 C25 1.4980(19) . ? C20 C21 1.4993(19) . ? C21 C22 1.5380(18) . ? C21 H21B 0.965(15) . ? C21 H21A 0.999(16) . ? C22 C23 1.5328(18) . ? C22 H22B 0.992(15) . ? C22 H22A 0.995(15) . ? C23 C24 1.5336(18) . ? C23 C23 1.545(2) 2_676 ? C23 H23A 0.987(14) . ? C24 C25 1.5382(18) . ? C24 H24B 0.997(15) . ? C24 H24A 0.993(15) . ? C25 H25A 0.992(16) . ? C25 H25B 0.987(15) . ? C26 C27 1.4972(19) . ? C26 C31 1.5002(19) . ? C27 C28 1.5330(19) . ? C27 H27B 0.988(16) . ? C27 H27A 0.992(18) . ? C28 C29 1.5309(18) . ? C28 H28B 0.988(15) . ? C28 H28A 1.008(15) . ? C29 C30 1.5311(18) . ? C29 C29 1.539(2) 2_766 ? C29 H29A 0.985(14) . ? C30 C31 1.5323(19) . ? C30 H30B 0.970(17) . ? C30 H30A 1.004(16) . ? C31 H31B 0.991(16) . ? C31 H31A 0.987(16) . ? 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 C17 O2 H2A 109.5(11) . . ? C11 O3 H3A 109.6(12) . . ? O1 C1 C3 118.87(11) . . ? O1 C1 C2 119.32(11) . . ? C3 C1 C2 121.81(11) . . ? C4 C2 C8 113.31(11) . . ? C4 C2 C5 107.44(11) . . ? C8 C2 C5 108.02(11) . . ? C4 C2 C1 112.62(11) . . ? C8 C2 C1 106.78(10) . . ? C5 C2 C1 108.50(11) . . ? C6 C3 C7 107.20(11) . . ? C6 C3 C14 108.60(10) . . ? C7 C3 C14 112.93(11) . . ? C6 C3 C1 108.57(11) . . ? C7 C3 C1 112.81(11) . . ? C14 C3 C1 106.61(10) . . ? C2 C4 H4C 113.8(9) . . ? C2 C4 H4B 109.9(9) . . ? H4C C4 H4B 107.7(13) . . ? C2 C4 H4A 109.1(9) . . ? H4C C4 H4A 109.1(12) . . ? H4B C4 H4A 107.0(13) . . ? C2 C5 H5C 109.5(9) . . ? C2 C5 H5B 112.6(9) . . ? H5C C5 H5B 108.4(13) . . ? C2 C5 H5A 108.7(9) . . ? H5C C5 H5A 108.2(12) . . ? H5B C5 H5A 109.3(13) . . ? C3 C6 H6C 108.4(9) . . ? C3 C6 H6B 112.0(9) . . ? H6C C6 H6B 108.7(12) . . ? C3 C6 H6A 110.6(9) . . ? H6C C6 H6A 108.9(13) . . ? H6B C6 H6A 108.1(13) . . ? C3 C7 H7C 113.8(9) . . ? C3 C7 H7B 108.8(9) . . ? H7C C7 H7B 108.3(12) . . ? C3 C7 H7A 109.9(9) . . ? H7C C7 H7A 107.7(12) . . ? H7B C7 H7A 108.3(12) . . ? C13 C8 C9 117.58(12) . . ? C13 C8 C2 123.20(12) . . ? C9 C8 C2 119.20(11) . . ? C10 C9 C8 121.68(13) . . ? C10 C9 H9A 117.8(9) . . ? C8 C9 H9A 120.6(9) . . ? C9 C10 C11 119.66(13) . . ? C9 C10 H10A 120.8(9) . . ? C11 C10 H10A 119.5(9) . . ? O3 C11 C12 117.91(12) . . ? O3 C11 C10 122.47(12) . . ? C12 C11 C10 119.61(12) . . ? C11 C12 C13 119.94(12) . . ? C11 C12 H12A 119.6(9) . . ? C13 C12 H12A 120.5(9) . . ? C8 C13 C12 121.47(12) . . ? C8 C13 H13A 118.7(9) . . ? C12 C13 H13A 119.8(9) . . ? C15 C14 C19 117.29(12) . . ? C15 C14 C3 123.20(11) . . ? C19 C14 C3 119.48(11) . . ? C16 C15 C14 121.44(12) . . ? C16 C15 H15A 118.3(8) . . ? C14 C15 H15A 120.3(8) . . ? C17 C16 C15 120.33(12) . . ? C17 C16 H16A 120.9(9) . . ? C15 C16 H16A 118.8(9) . . ? O2 C17 C16 118.03(12) . . ? O2 C17 C18 122.62(12) . . ? C16 C17 C18 119.34(12) . . ? C19 C18 C17 119.64(12) . . ? C19 C18 H18A 119.3(9) . . ? C17 C18 H18A 121.1(9) . . ? C18 C19 C14 121.95(12) . . ? C18 C19 H19A 117.7(8) . . ? C14 C19 H19A 120.3(8) . . ? O4 C20 C25 122.30(12) . . ? O4 C20 C21 122.78(12) . . ? C25 C20 C21 114.92(11) . . ? C20 C21 C22 112.30(11) . . ? C20 C21 H21B 107.1(9) . . ? C22 C21 H21B 109.5(9) . . ? C20 C21 H21A 111.2(9) . . ? C22 C21 H21A 110.8(9) . . ? H21B C21 H21A 105.7(12) . . ? C23 C22 C21 113.87(11) . . ? C23 C22 H22B 111.3(8) . . ? C21 C22 H22B 107.6(8) . . ? C23 C22 H22A 108.9(8) . . ? C21 C22 H22A 107.8(8) . . ? H22B C22 H22A 107.2(12) . . ? C22 C23 C24 109.02(11) . . ? C22 C23 C23 111.24(13) . 2_676 ? C24 C23 C23 111.97(13) . 2_676 ? C22 C23 H23A 108.7(8) . . ? C24 C23 H23A 108.6(8) . . ? C23 C23 H23A 107.2(8) 2_676 . ? C23 C24 C25 112.04(11) . . ? C23 C24 H24B 111.7(8) . . ? C25 C24 H24B 108.0(8) . . ? C23 C24 H24A 108.2(8) . . ? C25 C24 H24A 108.9(8) . . ? H24B C24 H24A 107.9(11) . . ? C20 C25 C24 110.80(11) . . ? C20 C25 H25A 106.6(9) . . ? C24 C25 H25A 108.4(9) . . ? C20 C25 H25B 109.8(9) . . ? C24 C25 H25B 111.6(8) . . ? H25A C25 H25B 109.5(12) . . ? O5 C26 C27 121.65(13) . . ? O5 C26 C31 122.26(13) . . ? C27 C26 C31 116.09(12) . . ? C26 C27 C28 111.09(11) . . ? C26 C27 H27B 109.2(9) . . ? C28 C27 H27B 112.8(9) . . ? C26 C27 H27A 106.1(10) . . ? C28 C27 H27A 108.0(10) . . ? H27B C27 H27A 109.4(13) . . ? C29 C28 C27 111.78(11) . . ? C29 C28 H28B 111.8(8) . . ? C27 C28 H28B 107.5(9) . . ? C29 C28 H28A 107.9(8) . . ? C27 C28 H28A 109.0(8) . . ? H28B C28 H28A 108.8(12) . . ? C28 C29 C30 108.03(11) . . ? C28 C29 C29 112.21(13) . 2_766 ? C30 C29 C29 111.89(13) . 2_766 ? C28 C29 H29A 107.8(8) . . ? C30 C29 H29A 108.2(8) . . ? C29 C29 H29A 108.6(8) 2_766 . ? C29 C30 C31 113.79(11) . . ? C29 C30 H30B 112.2(9) . . ? C31 C30 H30B 105.7(9) . . ? C29 C30 H30A 108.8(9) . . ? C31 C30 H30A 107.7(9) . . ? H30B C30 H30A 108.4(13) . . ? C26 C31 C30 113.66(11) . . ? C26 C31 H31B 110.9(9) . . ? C30 C31 H31B 111.9(9) . . ? C26 C31 H31A 104.2(9) . . ? C30 C31 H31A 109.3(9) . . ? H31B C31 H31A 106.3(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.287 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.041