data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 # SUBMISSION DETAILS _publ_contact_author ; Aidar T. Gubaidullin Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia #Structure Determination: #Dmitrii B. Krivolapov #Institute of Organic & #Physical Chemistry #Arbuzov Str.8 #420088 Kazan #Russia ; _publ_contact_author_phone ; 007 / 843 / 2727573 ; _publ_contact_author_fax ; 007 / 843 / 2732253 ; _publ_contact_author_email aidar@iopc.knc.ru # 3. TITLE AND AUTHOR LIST _publ_section_title ? _publ_author_address ? _journal_page_last ? # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. & Kennard, O. (1993). Chem. Des. Autom. News., 8, 31-37. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Flack, H.D. (1983). Acta Cryst. A39, 876-881. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326. Sheldrick, G.M. SHELXL93. Program for crystal structure refinement. University of G\\"ottingen, Germany, 1993. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of G\\"ottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1997. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; loop_ _publ_author_name A.Bredikhin D.Zakharychev Z.Bredikhina A.Gubaidullin R.Fayzullin # Attachment 'mef.cif' data_mef _database_code_depnum_ccdc_archive 'CCDC 693626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.0132(8) _cell_length_b 4.8558(3) _cell_length_c 16.3710(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.235(3) _cell_angle_gamma 90.00 _cell_volume 976.73(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7232 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 67.25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7208 _exptl_absorpt_correction_T_max 0.9292 _exptl_absorpt_process_details ; G.M. Sheldrick (1998a). SADABS v.2.01, Bruker. Siemens Area Detector Absorption Correction Program. Bruker AXS. Madison. Wisconsin. USA ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 11577 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 68.17 _reflns_number_total 3045 _reflns_number_gt 2893 _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^)+(0.0384P)^2^+0.1131P] 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 -0.0(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 3045 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _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 C1A C 0.86350(13) -0.0828(4) 0.43427(11) 0.0444(4) Uani 1 1 d . . . H11A H 0.8329 0.0341 0.3841 0.047(5) Uiso 1 1 calc R . . H12A H 0.9414 -0.0512 0.4568 0.058(5) Uiso 1 1 calc R . . C1B C 1.04405(14) 0.7680(5) 0.24658(11) 0.0534(4) Uani 1 1 d . . . H11B H 1.1072 0.6498 0.2693 0.070(6) Uiso 1 1 calc R . . H12B H 1.0505 0.8630 0.1964 0.065(6) Uiso 1 1 calc R . . C2A C 0.81241(13) -0.0153(4) 0.50283(10) 0.0409(4) Uani 1 1 d . . . C2B C 0.94240(14) 0.5925(4) 0.21910(10) 0.0490(4) Uani 1 1 d . . . C3A C 0.69045(13) -0.0546(4) 0.47349(10) 0.0453(4) Uani 1 1 d . . . H31A H 0.6720 -0.2449 0.4572 0.046(5) Uiso 1 1 calc R . . H32A H 0.6625 -0.0073 0.5198 0.045(4) Uiso 1 1 calc R . . C3B C 0.84001(14) 0.7604(4) 0.18016(10) 0.0499(4) Uani 1 1 d . . . H31B H 0.7759 0.6447 0.1678 0.065(6) Uiso 1 1 calc R . . H32B H 0.8353 0.9059 0.2194 0.060(6) Uiso 1 1 calc R . . C4A C 0.56989(17) 0.4670(6) 0.26115(12) 0.0699(6) Uani 1 1 d . . . H41A H 0.6125 0.3383 0.2413 0.105 Uiso 1 1 calc R . . H42A H 0.6173 0.5801 0.3059 0.105 Uiso 1 1 calc R . . H43A H 0.5287 0.5812 0.2138 0.105 Uiso 1 1 calc R . . C4B C 0.8757(2) 1.0305(7) -0.04809(16) 0.0929(9) Uani 1 1 d . . . H41B H 0.8706 0.8332 -0.0506 0.139 Uiso 1 1 calc R . . H42B H 0.9443 1.0837 -0.0069 0.139 Uiso 1 1 calc R . . H43B H 0.8702 1.1012 -0.1041 0.139 Uiso 1 1 calc R . . C5A C 0.53302(12) 0.1372(4) 0.36725(10) 0.0455(4) Uani 1 1 d . . . C5B C 0.77063(14) 1.0545(4) 0.05540(10) 0.0529(5) Uani 1 1 d . . . C6A C 0.49378(14) 0.3133(4) 0.29612(10) 0.0508(4) Uani 1 1 d . . . C6B C 0.78490(17) 1.1449(5) -0.02097(12) 0.0633(5) Uani 1 1 d . . . C7A C 0.38160(16) 0.3389(5) 0.25976(13) 0.0654(6) Uani 1 1 d . . . H7A H 0.3531 0.4548 0.2125 0.088(8) Uiso 1 1 calc R . . C7B C 0.7108(2) 1.3355(5) -0.07002(14) 0.0791(7) Uani 1 1 d . . . H7B H 0.7192 1.4010 -0.1208 0.113(10) Uiso 1 1 calc R . . C8A C 0.31129(15) 0.1971(5) 0.29185(14) 0.0690(6) Uani 1 1 d . . . H8A H 0.2365 0.2190 0.2664 0.091(8) Uiso 1 1 calc R . . C8B C 0.6256(2) 1.4309(5) -0.04626(15) 0.0825(7) Uani 1 1 d . . . H8B H 0.5775 1.5597 -0.0804 0.112(10) Uiso 1 1 calc R . . C9A C 0.35108(15) 0.0257(5) 0.36050(14) 0.0640(5) Uani 1 1 d . . . H9A H 0.3035 -0.0705 0.3818 0.068(6) Uiso 1 1 calc R . . C9B C 0.61199(19) 1.3352(5) 0.02814(15) 0.0761(7) Uani 1 1 d . . . H9B H 0.5542 1.3981 0.0445 0.099(9) Uiso 1 1 calc R . . C10A C 0.46299(14) -0.0063(5) 0.39913(12) 0.0558(5) Uani 1 1 d . . . H10A H 0.4904 -0.1239 0.4462 0.065(6) Uiso 1 1 calc R . . C10B C 0.68434(16) 1.1444(5) 0.07909(12) 0.0621(5) Uani 1 1 d . . . H10B H 0.6745 1.0774 0.1292 0.065(6) Uiso 1 1 calc R . . O1A O 0.84199(11) -0.3635(3) 0.41079(8) 0.0584(3) Uani 1 1 d . . . O1B O 1.04314(11) 0.9652(3) 0.31054(8) 0.0551(3) Uani 1 1 d . . . O2A O 0.84147(10) 0.2595(3) 0.53301(7) 0.0489(3) Uani 1 1 d . . . O2B O 0.93010(13) 0.4475(3) 0.29112(8) 0.0630(4) Uani 1 1 d . . . O3A O 0.64463(9) 0.1218(3) 0.40110(7) 0.0525(3) Uani 1 1 d . . . O3B O 0.84872(10) 0.8727(3) 0.10272(7) 0.0633(4) Uani 1 1 d . . . H1A H 0.873(2) -0.411(7) 0.3712(18) 0.107(9) Uiso 1 1 d . . . H1B H 1.0765(19) 0.886(6) 0.3634(16) 0.089(8) Uiso 1 1 d . . . H2A H 0.8425(13) -0.137(4) 0.5525(11) 0.044(5) Uiso 1 1 d . . . H2B H 0.9477(13) 0.452(4) 0.1754(11) 0.051(5) Uiso 1 1 d . . . H20A H 0.8297(18) 0.375(6) 0.4859(15) 0.079(7) Uiso 1 1 d . . . H20B H 0.9652(19) 0.300(7) 0.2988(15) 0.081(8) 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 C1A 0.0464(9) 0.0360(10) 0.0527(8) -0.0003(8) 0.0188(7) -0.0024(8) C1B 0.0563(10) 0.0549(12) 0.0468(9) -0.0011(9) 0.0141(7) 0.0123(10) C2A 0.0472(8) 0.0338(10) 0.0389(7) 0.0023(7) 0.0103(6) 0.0007(8) C2B 0.0706(11) 0.0391(10) 0.0391(8) -0.0009(7) 0.0207(8) 0.0075(9) C3A 0.0503(9) 0.0434(11) 0.0430(8) 0.0072(8) 0.0167(6) -0.0001(8) C3B 0.0561(10) 0.0488(11) 0.0416(8) 0.0040(8) 0.0117(7) -0.0019(9) C4A 0.0764(13) 0.0761(16) 0.0519(10) 0.0157(11) 0.0140(9) 0.0005(13) C4B 0.0927(16) 0.120(3) 0.0721(13) 0.0264(16) 0.0350(12) -0.0035(17) C5A 0.0422(8) 0.0463(10) 0.0461(8) -0.0049(8) 0.0119(7) 0.0017(8) C5B 0.0562(10) 0.0489(12) 0.0420(8) 0.0025(8) 0.0004(7) -0.0079(8) C6A 0.0537(9) 0.0499(12) 0.0440(8) -0.0029(8) 0.0096(7) 0.0009(9) C6B 0.0707(11) 0.0596(13) 0.0500(9) 0.0083(10) 0.0066(9) -0.0148(11) C7A 0.0592(11) 0.0646(15) 0.0583(11) -0.0028(10) 0.0004(9) 0.0091(10) C7B 0.0992(17) 0.0668(17) 0.0540(11) 0.0172(11) 0.0018(11) -0.0157(14) C8A 0.0447(10) 0.0757(18) 0.0774(13) -0.0151(12) 0.0078(9) 0.0028(10) C8B 0.0930(16) 0.0601(15) 0.0701(13) 0.0101(12) -0.0059(12) 0.0074(14) C9A 0.0481(10) 0.0685(15) 0.0784(12) -0.0138(11) 0.0248(9) -0.0070(10) C9B 0.0732(14) 0.0649(16) 0.0726(13) 0.0001(12) 0.0003(11) 0.0093(12) C10A 0.0484(9) 0.0579(13) 0.0624(10) 0.0012(10) 0.0201(8) -0.0027(9) C10B 0.0638(11) 0.0601(13) 0.0535(10) 0.0027(10) 0.0074(9) 0.0005(11) O1A 0.0867(9) 0.0348(7) 0.0653(8) -0.0027(6) 0.0410(7) -0.0032(7) O1B 0.0678(7) 0.0433(8) 0.0441(6) -0.0006(6) 0.0048(5) 0.0128(6) O2A 0.0605(7) 0.0384(7) 0.0425(6) -0.0040(5) 0.0096(5) -0.0038(6) O2B 0.1003(11) 0.0413(8) 0.0565(7) 0.0110(6) 0.0382(7) 0.0199(8) O3A 0.0402(6) 0.0610(8) 0.0534(6) 0.0174(6) 0.0117(5) -0.0003(6) O3B 0.0644(8) 0.0788(11) 0.0450(6) 0.0174(6) 0.0156(5) 0.0129(7) _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 C1A O1A 1.419(2) . ? C1A C2A 1.517(2) . ? C1A H11A 0.9700 . ? C1A H12A 0.9700 . ? C1B O1B 1.422(2) . ? C1B C2B 1.512(3) . ? C1B H11B 0.9700 . ? C1B H12B 0.9700 . ? C2A O2A 1.430(2) . ? C2A C3A 1.511(2) . ? C2A H2A 0.975(19) . ? C2B O2B 1.427(2) . ? C2B C3B 1.512(2) . ? C2B H2B 1.01(2) . ? C3A O3A 1.424(2) . ? C3A H31A 0.9700 . ? C3A H32A 0.9700 . ? C3B O3B 1.418(2) . ? C3B H31B 0.9700 . ? C3B H32B 0.9700 . ? C4A C6A 1.496(3) . ? C4A H41A 0.9600 . ? C4A H42A 0.9600 . ? C4A H43A 0.9600 . ? C4B C6B 1.499(4) . ? C4B H41B 0.9600 . ? C4B H42B 0.9600 . ? C4B H43B 0.9600 . ? C5A O3A 1.3755(19) . ? C5A C10A 1.379(3) . ? C5A C6A 1.399(3) . ? C5B C10B 1.374(3) . ? C5B O3B 1.376(2) . ? C5B C6B 1.394(2) . ? C6A C7A 1.389(3) . ? C6B C7B 1.386(3) . ? C7A C8A 1.380(3) . ? C7A H7A 0.9300 . ? C7B C8B 1.371(4) . ? C7B H7B 0.9300 . ? C8A C9A 1.356(3) . ? C8A H8A 0.9300 . ? C8B C9B 1.369(4) . ? C8B H8B 0.9300 . ? C9A C10A 1.392(3) . ? C9A H9A 0.9300 . ? C9B C10B 1.387(3) . ? C9B H9B 0.9300 . ? C10A H10A 0.9300 . ? C10B H10B 0.9300 . ? O1A H1A 0.90(3) . ? O1B H1B 0.91(3) . ? O2A H20A 0.92(3) . ? O2B H20B 0.84(3) . ? 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 O1A C1A C2A 108.21(14) . . ? O1A C1A H11A 110.1 . . ? C2A C1A H11A 110.1 . . ? O1A C1A H12A 110.1 . . ? C2A C1A H12A 110.1 . . ? H11A C1A H12A 108.4 . . ? O1B C1B C2B 112.33(14) . . ? O1B C1B H11B 109.1 . . ? C2B C1B H11B 109.1 . . ? O1B C1B H12B 109.1 . . ? C2B C1B H12B 109.1 . . ? H11B C1B H12B 107.9 . . ? O2A C2A C3A 110.98(14) . . ? O2A C2A C1A 109.07(14) . . ? C3A C2A C1A 114.08(13) . . ? O2A C2A H2A 106.7(11) . . ? C3A C2A H2A 106.3(10) . . ? C1A C2A H2A 109.4(10) . . ? O2B C2B C1B 110.95(14) . . ? O2B C2B C3B 106.94(14) . . ? C1B C2B C3B 112.62(16) . . ? O2B C2B H2B 107.8(11) . . ? C1B C2B H2B 109.6(10) . . ? C3B C2B H2B 108.8(10) . . ? O3A C3A C2A 107.26(13) . . ? O3A C3A H31A 110.3 . . ? C2A C3A H31A 110.3 . . ? O3A C3A H32A 110.3 . . ? C2A C3A H32A 110.3 . . ? H31A C3A H32A 108.5 . . ? O3B C3B C2B 105.38(13) . . ? O3B C3B H31B 110.7 . . ? C2B C3B H31B 110.7 . . ? O3B C3B H32B 110.7 . . ? C2B C3B H32B 110.7 . . ? H31B C3B H32B 108.8 . . ? C6A C4A H41A 109.5 . . ? C6A C4A H42A 109.5 . . ? H41A C4A H42A 109.5 . . ? C6A C4A H43A 109.5 . . ? H41A C4A H43A 109.5 . . ? H42A C4A H43A 109.5 . . ? C6B C4B H41B 109.5 . . ? C6B C4B H42B 109.5 . . ? H41B C4B H42B 109.5 . . ? C6B C4B H43B 109.5 . . ? H41B C4B H43B 109.5 . . ? H42B C4B H43B 109.5 . . ? O3A C5A C10A 124.17(16) . . ? O3A C5A C6A 114.59(15) . . ? C10A C5A C6A 121.24(16) . . ? C10B C5B O3B 124.43(16) . . ? C10B C5B C6B 121.05(18) . . ? O3B C5B C6B 114.52(17) . . ? C7A C6A C5A 117.08(18) . . ? C7A C6A C4A 121.76(18) . . ? C5A C6A C4A 121.16(15) . . ? C7B C6B C5B 117.2(2) . . ? C7B C6B C4B 122.8(2) . . ? C5B C6B C4B 120.0(2) . . ? C8A C7A C6A 121.8(2) . . ? C8A C7A H7A 119.1 . . ? C6A C7A H7A 119.1 . . ? C8B C7B C6B 122.3(2) . . ? C8B C7B H7B 118.8 . . ? C6B C7B H7B 118.8 . . ? C9A C8A C7A 120.10(18) . . ? C9A C8A H8A 120.0 . . ? C7A C8A H8A 120.0 . . ? C9B C8B C7B 119.5(2) . . ? C9B C8B H8B 120.3 . . ? C7B C8B H8B 120.3 . . ? C8A C9A C10A 120.1(2) . . ? C8A C9A H9A 119.9 . . ? C10A C9A H9A 119.9 . . ? C8B C9B C10B 120.0(2) . . ? C8B C9B H9B 120.0 . . ? C10B C9B H9B 120.0 . . ? C5A C10A C9A 119.62(19) . . ? C5A C10A H10A 120.2 . . ? C9A C10A H10A 120.2 . . ? C5B C10B C9B 119.9(2) . . ? C5B C10B H10B 120.1 . . ? C9B C10B H10B 120.1 . . ? C1A O1A H1A 111(2) . . ? C1B O1B H1B 107.3(18) . . ? C2A O2A H20A 108.9(16) . . ? C2B O2B H20B 110.0(17) . . ? C5A O3A C3A 117.72(13) . . ? C5B O3B C3B 119.21(14) . . ? 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 O1A C1A C2A O2A 174.83(13) . . . . ? O1A C1A C2A C3A -60.47(19) . . . . ? O1B C1B C2B O2B -59.2(2) . . . . ? O1B C1B C2B C3B 60.64(18) . . . . ? O2A C2A C3A O3A 64.11(17) . . . . ? C1A C2A C3A O3A -59.6(2) . . . . ? O2B C2B C3B O3B -172.60(15) . . . . ? C1B C2B C3B O3B 65.27(18) . . . . ? O3A C5A C6A C7A -179.43(17) . . . . ? C10A C5A C6A C7A 0.6(3) . . . . ? O3A C5A C6A C4A 0.5(3) . . . . ? C10A C5A C6A C4A -179.47(19) . . . . ? C10B C5B C6B C7B 2.2(3) . . . . ? O3B C5B C6B C7B -177.92(19) . . . . ? C10B C5B C6B C4B -176.2(2) . . . . ? O3B C5B C6B C4B 3.7(3) . . . . ? C5A C6A C7A C8A -0.1(3) . . . . ? C4A C6A C7A C8A 179.9(2) . . . . ? C5B C6B C7B C8B -0.9(4) . . . . ? C4B C6B C7B C8B 177.4(2) . . . . ? C6A C7A C8A C9A -0.4(3) . . . . ? C6B C7B C8B C9B -0.4(4) . . . . ? C7A C8A C9A C10A 0.4(3) . . . . ? C7B C8B C9B C10B 0.4(4) . . . . ? O3A C5A C10A C9A 179.46(18) . . . . ? C6A C5A C10A C9A -0.5(3) . . . . ? C8A C9A C10A C5A 0.0(3) . . . . ? O3B C5B C10B C9B 177.90(19) . . . . ? C6B C5B C10B C9B -2.2(3) . . . . ? C8B C9B C10B C5B 0.9(3) . . . . ? C10A C5A O3A C3A 0.2(3) . . . . ? C6A C5A O3A C3A -179.76(16) . . . . ? C2A C3A O3A C5A -175.06(15) . . . . ? C10B C5B O3B C3B 2.0(3) . . . . ? C6B C5B O3B C3B -177.89(17) . . . . ? C2B C3B O3B C5B -175.11(15) . . . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 68.17 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.110 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.028 # Attachment 'rac_7.cif' data_rac_7 _database_code_depnum_ccdc_archive 'CCDC 755204' #TrackingRef 'rac_7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 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_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P c' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 17.264(2) _cell_length_b 4.7225(7) _cell_length_c 11.9008(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.091(2) _cell_angle_gamma 90.00 _cell_volume 970.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2690 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 22.60 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9973 _exptl_absorpt_process_details ; G.M. Sheldrick (1998a). SADABS v.2.01, Bruker. Siemens Area Detector Absorption Correction Program. Bruker AXS. Madison. Wisconsin. USA ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 12167 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.94 _reflns_number_total 2236 _reflns_number_gt 1597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'APEX2 v2008.6-1 (Bruker AXS)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. ; _chemical_absolute_configuration unk _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^)+(0.1673P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2236 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2257 _refine_ls_wR_factor_gt 0.2048 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _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 O1A O 0.4649(2) 1.1510(8) 0.7256(3) 0.0580(9) Uani 1 1 d . . . H1A H 0.4376 1.2409 0.7692 0.087 Uiso 1 1 calc R . . C1A C 0.5142(3) 0.9656(12) 0.7876(4) 0.0502(11) Uani 1 1 d . . . H11A H 0.5591 1.0715 0.8132 0.060 Uiso 1 1 calc R . . H12A H 0.5326 0.8174 0.7378 0.060 Uiso 1 1 calc R . . O2A O 0.4245(2) 0.6157(9) 0.8455(4) 0.0618(10) Uani 1 1 d . . . H2A H 0.3910 0.5821 0.8924 0.093 Uiso 1 1 calc R . . C2A C 0.4756(3) 0.8307(10) 0.8877(5) 0.0490(11) Uani 1 1 d . . . H21A H 0.4444 0.9750 0.9258 0.059 Uiso 1 1 calc R . . O3A O 0.5894(2) 0.5421(8) 0.9138(3) 0.0512(8) Uani 1 1 d . . . C3A C 0.5345(4) 0.7136(12) 0.9713(4) 0.0552(13) Uani 1 1 d . . . H31A H 0.5609 0.8687 1.0087 0.066 Uiso 1 1 calc R . . H32A H 0.5081 0.6018 1.0279 0.066 Uiso 1 1 calc R . . C4A C 0.6450(3) 0.4141(11) 0.9762(4) 0.0455(10) Uani 1 1 d . . . C5A C 0.6510(3) 0.4368(13) 1.0931(5) 0.0554(12) Uani 1 1 d . . . H5A H 0.6171 0.5504 1.1337 0.066 Uiso 1 1 calc R . . C6A C 0.7101(4) 0.2821(12) 1.1476(5) 0.0580(13) Uani 1 1 d . . . H6A H 0.7138 0.2921 1.2255 0.070 Uiso 1 1 calc R . . C7A C 0.7623(3) 0.1177(12) 1.0904(4) 0.0528(12) Uani 1 1 d . . . C8A C 0.7562(3) 0.1029(12) 0.9740(5) 0.0547(12) Uani 1 1 d . . . H8A H 0.7909 -0.0070 0.9333 0.066 Uiso 1 1 calc R . . C9A C 0.6978(3) 0.2534(12) 0.9178(4) 0.0524(12) Uani 1 1 d . . . H9A H 0.6947 0.2444 0.8399 0.063 Uiso 1 1 calc R . . C10A C 0.8263(5) -0.0337(16) 1.1499(6) 0.0720(16) Uani 1 1 d . . . H13A H 0.8559 -0.1409 1.0966 0.108 Uiso 1 1 calc R . . H14A H 0.8047 -0.1593 1.2051 0.108 Uiso 1 1 calc R . . H15A H 0.8593 0.1018 1.1864 0.108 Uiso 1 1 calc R . . O1B O 0.3089(3) 0.6052(9) 0.4726(4) 0.0651(11) Uani 1 1 d . . . H1B H 0.3100 0.7693 0.4951 0.098 Uiso 1 1 calc R . . C1B C 0.2533(3) 0.4492(13) 0.5352(5) 0.0563(13) Uani 1 1 d . . . H11B H 0.2296 0.3080 0.4870 0.068 Uiso 1 1 calc R . . H12B H 0.2129 0.5763 0.5608 0.068 Uiso 1 1 calc R . . C2B C 0.2899(3) 0.3032(13) 0.6362(5) 0.0545(12) Uani 1 1 d . . . H21B H 0.3226 0.4421 0.6749 0.065 Uiso 1 1 calc R . . O2B O 0.3386(2) 0.0803(9) 0.5981(4) 0.0630(11) Uani 1 1 d . . . H2B H 0.3775 0.1475 0.5689 0.095 Uiso 1 1 calc R . . C3B C 0.2307(3) 0.1960(12) 0.7193(5) 0.0583(13) Uani 1 1 d . . . H31B H 0.2560 0.0836 0.7768 0.070 Uiso 1 1 calc R . . H32B H 0.2051 0.3545 0.7554 0.070 Uiso 1 1 calc R . . O3B O 0.1748(2) 0.0263(9) 0.6606(3) 0.0540(9) Uani 1 1 d . . . C4B C 0.1182(3) -0.0971(11) 0.7247(5) 0.0525(12) Uani 1 1 d . . . C5B C 0.0674(3) -0.2718(14) 0.6633(4) 0.0562(13) Uani 1 1 d . . . H5B H 0.0728 -0.2942 0.5861 0.067 Uiso 1 1 calc R . . C6B C 0.0090(4) -0.4094(14) 0.7216(5) 0.0615(14) Uani 1 1 d . . . H6B H -0.0252 -0.5241 0.6817 0.074 Uiso 1 1 calc R . . C7B C -0.0007(3) -0.3831(12) 0.8368(5) 0.0553(13) Uani 1 1 d . . . C8B C 0.0498(4) -0.2185(15) 0.8925(5) 0.0651(15) Uani 1 1 d . . . H8B H 0.0459 -0.2055 0.9702 0.078 Uiso 1 1 calc R . . C9B C 0.1085(4) -0.0643(12) 0.8374(5) 0.0580(13) Uani 1 1 d . . . H9B H 0.1403 0.0583 0.8776 0.070 Uiso 1 1 calc R . . C10B C -0.0642(4) -0.5411(19) 0.8969(6) 0.0751(17) Uani 1 1 d . . . H13B H -0.0938 -0.6481 0.8434 0.113 Uiso 1 1 calc R . . H14B H -0.0975 -0.4084 0.9343 0.113 Uiso 1 1 calc R . . H15B H -0.0418 -0.6672 0.9512 0.113 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 O1A 0.063(2) 0.055(2) 0.056(2) -0.0016(17) -0.0034(17) 0.0086(17) C1A 0.046(2) 0.052(3) 0.053(3) 0.000(2) 0.001(2) 0.004(2) O2A 0.050(2) 0.061(2) 0.075(3) -0.009(2) 0.0092(17) -0.0075(17) C2A 0.046(2) 0.037(2) 0.064(3) -0.003(2) 0.011(2) 0.0030(19) O3A 0.0553(18) 0.0553(19) 0.0430(17) 0.0015(16) 0.0033(14) 0.0090(16) C3A 0.072(3) 0.043(3) 0.051(3) 0.004(2) 0.016(2) 0.014(2) C4A 0.043(2) 0.045(3) 0.049(2) 0.004(2) 0.0020(18) -0.0054(19) C5A 0.060(3) 0.059(3) 0.047(3) -0.001(2) 0.003(2) -0.001(2) C6A 0.077(4) 0.049(3) 0.048(2) 0.000(2) -0.005(2) -0.004(3) C7A 0.053(3) 0.052(3) 0.053(3) 0.012(2) -0.011(2) -0.006(2) C8A 0.044(2) 0.058(3) 0.061(3) 0.006(3) 0.003(2) 0.003(2) C9A 0.047(2) 0.057(3) 0.054(3) -0.003(2) 0.000(2) 0.001(2) C10A 0.078(4) 0.070(4) 0.068(4) 0.010(3) -0.014(3) 0.007(3) O1B 0.073(2) 0.054(2) 0.068(2) -0.002(2) 0.015(2) -0.004(2) C1B 0.037(2) 0.068(3) 0.064(3) -0.008(3) -0.001(2) 0.000(2) C2B 0.048(2) 0.056(3) 0.060(3) -0.007(2) -0.003(2) -0.002(2) O2B 0.053(2) 0.055(2) 0.081(3) -0.013(2) -0.0079(19) 0.0030(18) C3B 0.061(3) 0.053(3) 0.061(3) -0.010(3) -0.011(2) -0.001(3) O3B 0.0521(19) 0.062(2) 0.0483(18) -0.0019(17) 0.0000(15) -0.0079(17) C4B 0.053(3) 0.046(3) 0.058(3) 0.000(2) -0.004(2) 0.005(2) C5B 0.052(3) 0.070(3) 0.046(2) 0.001(3) -0.006(2) 0.000(2) C6B 0.055(3) 0.070(4) 0.060(3) -0.007(3) -0.004(2) 0.002(3) C7B 0.060(3) 0.050(3) 0.056(3) 0.008(2) 0.005(2) 0.005(2) C8B 0.077(4) 0.070(4) 0.047(3) -0.001(3) 0.006(3) 0.005(3) C9B 0.066(3) 0.054(3) 0.055(3) -0.002(2) -0.009(2) 0.003(3) C10B 0.064(3) 0.096(5) 0.066(3) 0.004(4) 0.005(3) -0.006(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 O1A C1A 1.427(7) . ? O1A H1A 0.8200 . ? C1A C2A 1.508(7) . ? C1A H11A 0.9700 . ? C1A H12A 0.9700 . ? O2A C2A 1.435(7) . ? O2A H2A 0.8200 . ? C2A C3A 1.525(8) . ? C2A H21A 0.9800 . ? O3A C4A 1.355(6) . ? O3A C3A 1.423(6) . ? C3A H31A 0.9700 . ? C3A H32A 0.9700 . ? C4A C9A 1.376(7) . ? C4A C5A 1.399(8) . ? C5A C6A 1.412(9) . ? C5A H5A 0.9300 . ? C6A C7A 1.371(8) . ? C6A H6A 0.9300 . ? C7A C8A 1.391(8) . ? C7A C10A 1.494(9) . ? C8A C9A 1.402(8) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A H13A 0.9600 . ? C10A H14A 0.9600 . ? C10A H15A 0.9600 . ? O1B C1B 1.422(7) . ? O1B H1B 0.8200 . ? C1B C2B 1.522(9) . ? C1B H11B 0.9700 . ? C1B H12B 0.9700 . ? C2B O2B 1.421(7) . ? C2B C3B 1.511(8) . ? C2B H21B 0.9800 . ? O2B H2B 0.8200 . ? C3B O3B 1.435(7) . ? C3B H31B 0.9700 . ? C3B H32B 0.9700 . ? O3B C4B 1.370(7) . ? C4B C9B 1.360(8) . ? C4B C5B 1.408(8) . ? C5B C6B 1.386(9) . ? C5B H5B 0.9300 . ? C6B C7B 1.388(9) . ? C6B H6B 0.9300 . ? C7B C8B 1.342(9) . ? C7B C10B 1.507(9) . ? C8B C9B 1.411(9) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B H13B 0.9600 . ? C10B H14B 0.9600 . ? C10B H15B 0.9600 . ? 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 C1A O1A H1A 109.5 . . ? O1A C1A C2A 113.8(4) . . ? O1A C1A H11A 108.8 . . ? C2A C1A H11A 108.8 . . ? O1A C1A H12A 108.8 . . ? C2A C1A H12A 108.8 . . ? H11A C1A H12A 107.7 . . ? C2A O2A H2A 109.5 . . ? O2A C2A C1A 107.2(5) . . ? O2A C2A C3A 112.4(4) . . ? C1A C2A C3A 111.9(4) . . ? O2A C2A H21A 108.4 . . ? C1A C2A H21A 108.4 . . ? C3A C2A H21A 108.4 . . ? C4A O3A C3A 117.5(4) . . ? O3A C3A C2A 109.7(4) . . ? O3A C3A H31A 109.7 . . ? C2A C3A H31A 109.7 . . ? O3A C3A H32A 109.7 . . ? C2A C3A H32A 109.7 . . ? H31A C3A H32A 108.2 . . ? O3A C4A C9A 116.0(4) . . ? O3A C4A C5A 124.2(5) . . ? C9A C4A C5A 119.8(5) . . ? C4A C5A C6A 118.0(5) . . ? C4A C5A H5A 121.0 . . ? C6A C5A H5A 121.0 . . ? C7A C6A C5A 122.7(5) . . ? C7A C6A H6A 118.7 . . ? C5A C6A H6A 118.7 . . ? C6A C7A C8A 118.3(5) . . ? C6A C7A C10A 121.4(5) . . ? C8A C7A C10A 120.2(6) . . ? C7A C8A C9A 120.2(5) . . ? C7A C8A H8A 119.9 . . ? C9A C8A H8A 119.9 . . ? C4A C9A C8A 121.0(5) . . ? C4A C9A H9A 119.5 . . ? C8A C9A H9A 119.5 . . ? C7A C10A H13A 109.5 . . ? C7A C10A H14A 109.5 . . ? H13A C10A H14A 109.5 . . ? C7A C10A H15A 109.5 . . ? H13A C10A H15A 109.5 . . ? H14A C10A H15A 109.5 . . ? C1B O1B H1B 109.5 . . ? O1B C1B C2B 111.6(5) . . ? O1B C1B H11B 109.3 . . ? C2B C1B H11B 109.3 . . ? O1B C1B H12B 109.3 . . ? C2B C1B H12B 109.3 . . ? H11B C1B H12B 108.0 . . ? O2B C2B C3B 111.2(5) . . ? O2B C2B C1B 109.2(4) . . ? C3B C2B C1B 112.8(4) . . ? O2B C2B H21B 107.8 . . ? C3B C2B H21B 107.8 . . ? C1B C2B H21B 107.8 . . ? C2B O2B H2B 109.5 . . ? O3B C3B C2B 108.9(5) . . ? O3B C3B H31B 109.9 . . ? C2B C3B H31B 109.9 . . ? O3B C3B H32B 109.9 . . ? C2B C3B H32B 109.9 . . ? H31B C3B H32B 108.3 . . ? C4B O3B C3B 116.5(4) . . ? C9B C4B O3B 126.1(5) . . ? C9B C4B C5B 120.1(5) . . ? O3B C4B C5B 113.8(5) . . ? C6B C5B C4B 117.9(5) . . ? C6B C5B H5B 121.1 . . ? C4B C5B H5B 121.1 . . ? C5B C6B C7B 122.8(6) . . ? C5B C6B H6B 118.6 . . ? C7B C6B H6B 118.6 . . ? C8B C7B C6B 117.4(5) . . ? C8B C7B C10B 121.7(6) . . ? C6B C7B C10B 120.9(6) . . ? C7B C8B C9B 122.4(5) . . ? C7B C8B H8B 118.8 . . ? C9B C8B H8B 118.8 . . ? C4B C9B C8B 119.3(5) . . ? C4B C9B H9B 120.4 . . ? C8B C9B H9B 120.4 . . ? C7B C10B H13B 109.5 . . ? C7B C10B H14B 109.5 . . ? H13B C10B H14B 109.5 . . ? C7B C10B H15B 109.5 . . ? H13B C10B H15B 109.5 . . ? H14B C10B H15B 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 O1A C1A C2A O2A 74.6(5) . . . . ? O1A C1A C2A C3A -161.8(4) . . . . ? C4A O3A C3A C2A -178.2(4) . . . . ? O2A C2A C3A O3A 70.6(5) . . . . ? C1A C2A C3A O3A -50.0(6) . . . . ? C3A O3A C4A C9A -179.1(4) . . . . ? C3A O3A C4A C5A 1.0(7) . . . . ? O3A C4A C5A C6A 177.4(5) . . . . ? C9A C4A C5A C6A -2.5(8) . . . . ? C4A C5A C6A C7A 1.5(9) . . . . ? C5A C6A C7A C8A -0.2(9) . . . . ? C5A C6A C7A C10A 177.4(6) . . . . ? C6A C7A C8A C9A -0.1(8) . . . . ? C10A C7A C8A C9A -177.7(5) . . . . ? O3A C4A C9A C8A -177.7(5) . . . . ? C5A C4A C9A C8A 2.3(8) . . . . ? C7A C8A C9A C4A -1.0(8) . . . . ? O1B C1B C2B O2B -69.7(6) . . . . ? O1B C1B C2B C3B 166.1(4) . . . . ? O2B C2B C3B O3B -70.9(6) . . . . ? C1B C2B C3B O3B 52.1(6) . . . . ? C2B C3B O3B C4B 177.6(4) . . . . ? C3B O3B C4B C9B 2.8(8) . . . . ? C3B O3B C4B C5B -177.0(4) . . . . ? C9B C4B C5B C6B -0.9(8) . . . . ? O3B C4B C5B C6B 179.0(5) . . . . ? C4B C5B C6B C7B -0.5(9) . . . . ? C5B C6B C7B C8B -0.6(9) . . . . ? C5B C6B C7B C10B -178.9(6) . . . . ? C6B C7B C8B C9B 3.1(9) . . . . ? C10B C7B C8B C9B -178.6(6) . . . . ? O3B C4B C9B C8B -176.5(5) . . . . ? C5B C4B C9B C8B 3.3(8) . . . . ? C7B C8B C9B C4B -4.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.566 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.076 # Attachment 'scal_S_7.cif' data_scal_S_7 _database_code_depnum_ccdc_archive 'CCDC 755205' #TrackingRef 'scal_S_7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.8768(2) _cell_length_b 7.2147(3) _cell_length_c 28.5203(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1003.48(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6289 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 67.13 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6700 _exptl_absorpt_correction_T_max 0.9052 _exptl_absorpt_process_details ; G.M. Sheldrick (1998a). SADABS v.2.01, Bruker. Siemens Area Detector Absorption Correction Program. Bruker AXS. Madison. Wisconsin. USA ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 7867 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 6.21 _diffrn_reflns_theta_max 67.35 _reflns_number_total 1673 _reflns_number_gt 1630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'APEX2 v2008.6-1 (Bruker AXS)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. ; _chemical_absolute_configuration rmad _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^)+(0.0438P)^2^+0.0862P] 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 0.0(2) _refine_ls_number_reflns 1673 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.4593(3) 0.69819(17) 0.80816(5) 0.0545(3) Uani 1 1 d . . . H11 H 0.3744 0.7375 0.8373 0.065 Uiso 1 1 calc R . . H12 H 0.5803 0.7965 0.7976 0.065 Uiso 1 1 calc R . . C2 C 0.6234(3) 0.52472(17) 0.81657(4) 0.0471(3) Uani 1 1 d . . . H21 H 0.7476 0.5465 0.8430 0.057 Uiso 1 1 calc R . . C3 C 0.4483(3) 0.35742(17) 0.82758(5) 0.0482(3) Uani 1 1 d . . . H31 H 0.3366 0.3247 0.8007 0.058 Uiso 1 1 calc R . . H32 H 0.5631 0.2522 0.8355 0.058 Uiso 1 1 calc R . . C4 C 0.1170(3) 0.26998(18) 0.88514(4) 0.0495(3) Uani 1 1 d . . . C5 C -0.0339(3) 0.3198(2) 0.92417(5) 0.0650(4) Uani 1 1 d . . . H5 H -0.0207 0.4395 0.9361 0.078 Uiso 1 1 calc R . . C6 C -0.2037(4) 0.1929(3) 0.94546(5) 0.0725(4) Uani 1 1 d . . . H6 H -0.3049 0.2289 0.9716 0.087 Uiso 1 1 calc R . . C7 C -0.2280(3) 0.0126(2) 0.92904(5) 0.0651(4) Uani 1 1 d . . . C8 C -0.0769(3) -0.0331(2) 0.89003(6) 0.0640(4) Uani 1 1 d . . . H8 H -0.0892 -0.1531 0.8783 0.077 Uiso 1 1 calc R . . C9 C 0.0935(3) 0.0927(2) 0.86741(5) 0.0570(3) Uani 1 1 d . . . H9 H 0.1903 0.0580 0.8407 0.068 Uiso 1 1 calc R . . C10 C -0.4123(4) -0.1254(3) 0.95305(7) 0.0917(6) Uani 1 1 d . . . H13 H -0.4262 -0.2353 0.9342 0.138 Uiso 1 1 calc R . . H14 H -0.5912 -0.0722 0.9571 0.138 Uiso 1 1 calc R . . H15 H -0.3370 -0.1566 0.9831 0.138 Uiso 1 1 calc R . . O1 O 0.2538(2) 0.66670(15) 0.77392(4) 0.0731(3) Uani 1 1 d . . . O2 O 0.7826(2) 0.47561(14) 0.77670(4) 0.0624(3) Uani 1 1 d . . . O3 O 0.2787(2) 0.40637(12) 0.86629(3) 0.0564(3) Uani 1 1 d . . . H1 H 0.234(4) 0.761(3) 0.7573(6) 0.080(5) Uiso 1 1 d . . . H2 H 0.937(4) 0.544(3) 0.7761(6) 0.083(6) 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 C1 0.0462(7) 0.0454(6) 0.0720(8) 0.0042(6) 0.0013(6) -0.0004(6) C2 0.0374(6) 0.0470(6) 0.0570(7) -0.0064(5) -0.0039(5) 0.0003(5) C3 0.0424(6) 0.0437(6) 0.0586(7) -0.0031(5) 0.0005(6) 0.0041(5) C4 0.0452(6) 0.0501(6) 0.0530(6) 0.0048(5) -0.0023(6) 0.0050(6) C5 0.0731(10) 0.0669(9) 0.0550(8) -0.0043(7) 0.0048(7) 0.0025(8) C6 0.0686(10) 0.0926(12) 0.0563(7) 0.0049(8) 0.0099(7) 0.0005(10) C7 0.0486(7) 0.0814(10) 0.0653(8) 0.0194(7) -0.0070(7) -0.0042(9) C8 0.0549(8) 0.0563(8) 0.0808(9) 0.0058(7) -0.0025(8) -0.0041(7) C9 0.0505(7) 0.0522(7) 0.0683(8) -0.0017(6) 0.0056(7) 0.0027(6) C10 0.0713(11) 0.1118(15) 0.0922(12) 0.0353(11) -0.0001(10) -0.0186(12) O1 0.0462(5) 0.0702(6) 0.1030(8) 0.0365(6) -0.0181(6) -0.0143(6) O2 0.0427(5) 0.0630(6) 0.0815(7) -0.0221(5) 0.0115(5) -0.0113(5) O3 0.0610(6) 0.0467(4) 0.0615(5) -0.0028(4) 0.0093(5) 0.0009(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 C1 O1 1.4178(17) . ? C1 C2 1.5046(17) . ? C1 H11 0.9700 . ? C1 H12 0.9700 . ? C2 O2 1.4218(16) . ? C2 C3 1.5114(18) . ? C2 H21 0.9800 . ? C3 O3 1.4240(15) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? C4 O3 1.3709(16) . ? C4 C9 1.380(2) . ? C4 C5 1.3822(19) . ? C5 C6 1.376(2) . ? C5 H5 0.9300 . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 C8 1.375(2) . ? C7 C10 1.506(2) . ? C8 C9 1.389(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H13 0.9600 . ? C10 H14 0.9600 . ? C10 H15 0.9600 . ? O1 H1 0.836(19) . ? O2 H2 0.90(2) . ? 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 O1 C1 C2 110.63(11) . . ? O1 C1 H11 109.5 . . ? C2 C1 H11 109.5 . . ? O1 C1 H12 109.5 . . ? C2 C1 H12 109.5 . . ? H11 C1 H12 108.1 . . ? O2 C2 C1 111.73(11) . . ? O2 C2 C3 106.00(10) . . ? C1 C2 C3 113.40(10) . . ? O2 C2 H21 108.5 . . ? C1 C2 H21 108.5 . . ? C3 C2 H21 108.5 . . ? O3 C3 C2 106.92(10) . . ? O3 C3 H31 110.3 . . ? C2 C3 H31 110.3 . . ? O3 C3 H32 110.3 . . ? C2 C3 H32 110.3 . . ? H31 C3 H32 108.6 . . ? O3 C4 C9 124.70(12) . . ? O3 C4 C5 115.82(12) . . ? C9 C4 C5 119.47(13) . . ? C6 C5 C4 120.18(15) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 121.77(15) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C8 C7 C6 116.88(14) . . ? C8 C7 C10 121.99(18) . . ? C6 C7 C10 121.13(17) . . ? C7 C8 C9 122.68(15) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C4 C9 C8 119.00(14) . . ? C4 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C7 C10 H13 109.5 . . ? C7 C10 H14 109.5 . . ? H13 C10 H14 109.5 . . ? C7 C10 H15 109.5 . . ? H13 C10 H15 109.5 . . ? H14 C10 H15 109.5 . . ? C1 O1 H1 109.8(13) . . ? C2 O2 H2 109.8(11) . . ? C4 O3 C3 117.40(10) . . ? 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 O2 67.33(13) . . . . ? O1 C1 C2 C3 -52.39(15) . . . . ? O2 C2 C3 O3 -177.66(9) . . . . ? C1 C2 C3 O3 -54.73(14) . . . . ? O3 C4 C5 C6 179.63(13) . . . . ? C9 C4 C5 C6 0.7(2) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.8(2) . . . . ? C5 C6 C7 C10 179.29(15) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? C10 C7 C8 C9 179.85(15) . . . . ? O3 C4 C9 C8 179.66(12) . . . . ? C5 C4 C9 C8 -1.6(2) . . . . ? C7 C8 C9 C4 1.2(2) . . . . ? C9 C4 O3 C3 -4.45(18) . . . . ? C5 C4 O3 C3 176.73(11) . . . . ? C2 C3 O3 C4 -174.70(10) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 67.35 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.080 _refine_diff_density_min -0.096 _refine_diff_density_rms 0.025 # Attachment '- scal_S_2_modif.cif' data_bredikh_sm16 _database_code_depnum_ccdc_archive 'CCDC 826679' #TrackingRef '- scal_S_2_modif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 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_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 12.513(1) _cell_length_b 4.9317(5) _cell_length_c 16.282(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.159(6) _cell_angle_gamma 90.00 _cell_volume 996.9(1) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 949 _cell_measurement_theta_min 3.88 _cell_measurement_theta_max 19.73 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9536 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details ; G.M. Sheldrick (1998a). SADABS v.2.01, Bruker. Siemens Area Detector Absorption Correction Program. Bruker AXS. Madison. Wisconsin. USA ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 6120 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.98 _reflns_number_total 3587 _reflns_number_gt 1746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'APEX2 v2008.6-1 (Bruker AXS)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. ; _chemical_absolute_configuration rm _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^)+(0.0357P)^2^+0.0000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3587 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1314 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.000 _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 C1B C 0.4098(2) 0.5683(9) 0.74685(17) 0.0698(10) Uani 1 1 d . . . H11B H 0.3962 0.4729 0.7966 0.084 Uiso 1 1 calc R . . H12B H 0.3474 0.6805 0.7293 0.084 Uiso 1 1 calc R . . C2B C 0.5059(2) 0.7475(8) 0.76705(16) 0.0611(9) Uani 1 1 d . . . H21B H 0.4930 0.8731 0.8114 0.073 Uiso 1 1 calc R . . C3B C 0.6078(2) 0.5923(8) 0.79235(16) 0.0613(9) Uani 1 1 d . . . H31B H 0.6255 0.4829 0.7464 0.074 Uiso 1 1 calc R . . H32B H 0.6668 0.7171 0.8079 0.074 Uiso 1 1 calc R . . C4B C 0.6807(3) 0.2667(8) 0.89325(18) 0.0687(10) Uani 1 1 d . . . C5B C 0.6608(3) 0.0949(9) 0.95554(19) 0.0783(11) Uani 1 1 d . . . H5B H 0.5924 0.0885 0.9721 0.094 Uiso 1 1 calc R . . C6B C 0.7422(4) -0.0705(9) 0.9944(2) 0.0877(12) Uani 1 1 d . . . C7B C 0.8433(4) -0.0482(12) 0.9680(3) 0.1082(17) Uani 1 1 d . . . H7B H 0.8995 -0.1529 0.9938 0.130 Uiso 1 1 calc R . . C8B C 0.8629(3) 0.1213(12) 0.9058(3) 0.1072(17) Uani 1 1 d . . . H8B H 0.9312 0.1284 0.8890 0.129 Uiso 1 1 calc R . . C9B C 0.7808(3) 0.2845(10) 0.8670(2) 0.0853(12) Uani 1 1 d . . . H9B H 0.7933 0.4022 0.8246 0.102 Uiso 1 1 calc R . . C10B C 0.7196(4) -0.2583(12) 1.0613(2) 0.131(2) Uani 1 1 d . . . H15B H 0.6431 -0.2769 1.0607 0.197 Uiso 1 1 calc R . . H13B H 0.7504 -0.1870 1.1139 0.197 Uiso 1 1 calc R . . H14B H 0.7506 -0.4325 1.0527 0.197 Uiso 1 1 calc R . . C1A C 0.3781(2) 0.9325(7) 0.44736(17) 0.0538(8) Uani 1 1 d . . . H11A H 0.4525 0.9190 0.4723 0.065 Uiso 1 1 calc R . . H12A H 0.3680 0.8124 0.3999 0.065 Uiso 1 1 calc R . . C2A C 0.30384(18) 0.8508(7) 0.50931(14) 0.0448(7) Uani 1 1 d . . . H21A H 0.3174 0.9746 0.5565 0.054 Uiso 1 1 calc R . . C3A C 0.18658(17) 0.8729(8) 0.47685(14) 0.0496(8) Uani 1 1 d . . . H31A H 0.1424 0.8220 0.5193 0.059 Uiso 1 1 calc R . . H32A H 0.1688 1.0575 0.4596 0.059 Uiso 1 1 calc R . . C4A C 0.0642(2) 0.6572(7) 0.37301(16) 0.0533(9) Uani 1 1 d . . . C5A C 0.0517(2) 0.4705(8) 0.30943(17) 0.0610(9) Uani 1 1 d . . . H5A H 0.1115 0.3789 0.2948 0.073 Uiso 1 1 calc R . . C6A C -0.0508(3) 0.4181(8) 0.26678(17) 0.0685(10) Uani 1 1 d . . . C7A C -0.1370(2) 0.5600(10) 0.2909(2) 0.0756(12) Uani 1 1 d . . . H7A H -0.2057 0.5286 0.2636 0.091 Uiso 1 1 calc R . . C8A C -0.1239(2) 0.7459(9) 0.35417(19) 0.0709(11) Uani 1 1 d . . . H8A H -0.1836 0.8369 0.3692 0.085 Uiso 1 1 calc R . . C9A C -0.0233(2) 0.7986(8) 0.39543(16) 0.0587(9) Uani 1 1 d . . . H9A H -0.0142 0.9268 0.4376 0.070 Uiso 1 1 calc R . . C10A C -0.0635(3) 0.2105(10) 0.19868(19) 0.0984(14) Uani 1 1 d . . . H15A H -0.1115 0.0701 0.2123 0.148 Uiso 1 1 calc R . . H13A H 0.0054 0.1332 0.1925 0.148 Uiso 1 1 calc R . . H14A H -0.0927 0.2956 0.1477 0.148 Uiso 1 1 calc R . . O1B O 0.42162(15) 0.3761(5) 0.68415(11) 0.0677(6) Uani 1 1 d . . . H1B H 0.4037 0.4449 0.6387 0.101 Uiso 1 1 calc R . . O2B O 0.52564(16) 0.8977(5) 0.69589(11) 0.0768(7) Uani 1 1 d . . . H2B H 0.4963 1.0462 0.6964 0.115 Uiso 1 1 calc R . . O3B O 0.59261(15) 0.4249(6) 0.85976(11) 0.0735(7) Uani 1 1 d . . . O1A O 0.35465(16) 1.2020(5) 0.42205(11) 0.0667(6) Uani 1 1 d . . . H1A H 0.3874 1.2396 0.3829 0.100 Uiso 1 1 calc R . . O2A O 0.33107(13) 0.5853(5) 0.53889(10) 0.0549(6) Uani 1 1 d . . . H2A H 0.3303 0.4811 0.4996 0.082 Uiso 1 1 calc R . . O3A O 0.16845(12) 0.6936(5) 0.40839(11) 0.0610(6) 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 C1B 0.0695(19) 0.078(3) 0.0617(18) 0.008(2) 0.0060(15) 0.024(2) C2B 0.088(2) 0.047(2) 0.0494(15) 0.0025(16) 0.0110(14) 0.017(2) C3B 0.0748(18) 0.051(2) 0.0562(16) 0.0053(18) 0.0002(13) 0.0078(19) C4B 0.090(2) 0.056(3) 0.0545(18) -0.0054(19) -0.0152(16) 0.009(2) C5B 0.112(3) 0.061(3) 0.0573(17) -0.009(2) -0.0103(17) 0.003(2) C6B 0.136(3) 0.060(3) 0.057(2) -0.013(2) -0.027(2) 0.017(3) C7B 0.134(4) 0.082(4) 0.095(3) -0.018(3) -0.042(3) 0.037(3) C8B 0.098(3) 0.113(5) 0.105(3) -0.008(3) -0.013(2) 0.036(3) C9B 0.085(2) 0.081(4) 0.085(2) -0.009(2) -0.0083(19) 0.016(2) C10B 0.240(6) 0.077(4) 0.067(2) 0.002(3) -0.018(3) 0.025(4) C1A 0.0521(15) 0.041(2) 0.0697(17) 0.0036(17) 0.0117(13) 0.0025(16) C2A 0.0484(14) 0.037(2) 0.0467(13) -0.0029(15) -0.0014(11) 0.0046(14) C3A 0.0476(14) 0.049(2) 0.0521(14) -0.0084(16) 0.0073(11) 0.0043(14) C4A 0.0506(16) 0.055(3) 0.0533(15) 0.0064(17) 0.0009(12) -0.0030(16) C5A 0.0676(18) 0.053(3) 0.0597(16) 0.0040(18) -0.0022(14) -0.0048(18) C6A 0.090(2) 0.053(3) 0.0569(17) 0.0143(18) -0.0137(17) -0.031(2) C7A 0.0563(19) 0.087(3) 0.079(2) 0.028(2) -0.0097(17) -0.023(2) C8A 0.0514(17) 0.083(3) 0.0772(19) 0.021(2) 0.0038(15) -0.0037(18) C9A 0.0453(15) 0.066(3) 0.0641(16) 0.0094(17) 0.0027(13) 0.0032(16) C10A 0.125(3) 0.084(4) 0.079(2) 0.000(3) -0.0149(19) -0.043(3) O1B 0.0840(13) 0.0513(17) 0.0639(11) 0.0056(12) -0.0057(9) 0.0137(13) O2B 0.1119(15) 0.0522(18) 0.0690(12) 0.0116(13) 0.0223(11) 0.0233(15) O3B 0.0807(13) 0.073(2) 0.0645(11) 0.0154(13) -0.0005(10) 0.0148(14) O1A 0.0926(14) 0.0399(16) 0.0719(12) 0.0016(12) 0.0273(10) 0.0028(13) O2A 0.0701(12) 0.0439(15) 0.0483(9) 0.0013(10) -0.0023(8) 0.0064(11) O3A 0.0440(9) 0.0695(17) 0.0667(11) -0.0265(12) -0.0047(8) 0.0063(10) _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 C1B O1B 1.414(4) . ? C1B C2B 1.496(5) . ? C1B H11B 0.9700 . ? C1B H12B 0.9700 . ? C2B O2B 1.422(3) . ? C2B C3B 1.499(4) . ? C2B H21B 0.9800 . ? C3B O3B 1.405(4) . ? C3B H31B 0.9700 . ? C3B H32B 0.9700 . ? C4B C5B 1.368(5) . ? C4B C9B 1.376(5) . ? C4B O3B 1.404(4) . ? C5B C6B 1.394(5) . ? C5B H5B 0.9300 . ? C6B C7B 1.390(6) . ? C6B C10B 1.484(6) . ? C7B C8B 1.359(7) . ? C7B H7B 0.9300 . ? C8B C9B 1.392(5) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B H15B 0.9600 . ? C10B H13B 0.9600 . ? C10B H14B 0.9600 . ? C1A O1A 1.412(4) . ? C1A C2A 1.509(3) . ? C1A H11A 0.9700 . ? C1A H12A 0.9700 . ? C2A O2A 1.422(4) . ? C2A C3A 1.500(3) . ? C2A H21A 0.9800 . ? C3A O3A 1.419(3) . ? C3A H31A 0.9700 . ? C3A H32A 0.9700 . ? C4A O3A 1.370(3) . ? C4A C5A 1.380(4) . ? C4A C9A 1.385(4) . ? C5A C6A 1.405(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.383(5) . ? C6A C10A 1.503(5) . ? C7A C8A 1.373(5) . ? C7A H7A 0.9300 . ? C8A C9A 1.376(4) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A H15A 0.9600 . ? C10A H13A 0.9600 . ? C10A H14A 0.9600 . ? O1B H1B 0.8200 . ? O2B H2B 0.8200 . ? O1A H1A 0.8200 . ? O2A H2A 0.8200 . ? 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 O1B C1B C2B 113.6(2) . . ? O1B C1B H11B 108.8 . . ? C2B C1B H11B 108.8 . . ? O1B C1B H12B 108.8 . . ? C2B C1B H12B 108.8 . . ? H11B C1B H12B 107.7 . . ? O2B C2B C3B 105.2(2) . . ? O2B C2B C1B 110.2(2) . . ? C3B C2B C1B 113.0(3) . . ? O2B C2B H21B 109.4 . . ? C3B C2B H21B 109.4 . . ? C1B C2B H21B 109.4 . . ? O3B C3B C2B 108.8(2) . . ? O3B C3B H31B 109.9 . . ? C2B C3B H31B 109.9 . . ? O3B C3B H32B 109.9 . . ? C2B C3B H32B 109.9 . . ? H31B C3B H32B 108.3 . . ? C5B C4B C9B 121.8(3) . . ? C5B C4B O3B 115.2(3) . . ? C9B C4B O3B 123.0(3) . . ? C4B C5B C6B 120.6(4) . . ? C4B C5B H5B 119.7 . . ? C6B C5B H5B 119.7 . . ? C7B C6B C5B 117.0(4) . . ? C7B C6B C10B 122.8(5) . . ? C5B C6B C10B 120.2(5) . . ? C8B C7B C6B 122.4(4) . . ? C8B C7B H7B 118.8 . . ? C6B C7B H7B 118.8 . . ? C7B C8B C9B 120.1(4) . . ? C7B C8B H8B 119.9 . . ? C9B C8B H8B 119.9 . . ? C4B C9B C8B 118.1(4) . . ? C4B C9B H9B 120.9 . . ? C8B C9B H9B 120.9 . . ? C6B C10B H15B 109.5 . . ? C6B C10B H13B 109.5 . . ? H15B C10B H13B 109.5 . . ? C6B C10B H14B 109.5 . . ? H15B C10B H14B 109.5 . . ? H13B C10B H14B 109.5 . . ? O1A C1A C2A 108.9(2) . . ? O1A C1A H11A 109.9 . . ? C2A C1A H11A 109.9 . . ? O1A C1A H12A 109.9 . . ? C2A C1A H12A 109.9 . . ? H11A C1A H12A 108.3 . . ? O2A C2A C3A 111.6(2) . . ? O2A C2A C1A 109.3(2) . . ? C3A C2A C1A 113.69(19) . . ? O2A C2A H21A 107.3 . . ? C3A C2A H21A 107.3 . . ? C1A C2A H21A 107.3 . . ? O3A C3A C2A 106.6(2) . . ? O3A C3A H31A 110.4 . . ? C2A C3A H31A 110.4 . . ? O3A C3A H32A 110.4 . . ? C2A C3A H32A 110.4 . . ? H31A C3A H32A 108.6 . . ? O3A C4A C5A 114.6(3) . . ? O3A C4A C9A 124.5(3) . . ? C5A C4A C9A 121.0(2) . . ? C4A C5A C6A 120.3(3) . . ? C4A C5A H5A 119.8 . . ? C6A C5A H5A 119.8 . . ? C7A C6A C5A 117.6(3) . . ? C7A C6A C10A 122.6(3) . . ? C5A C6A C10A 119.8(4) . . ? C8A C7A C6A 121.8(3) . . ? C8A C7A H7A 119.1 . . ? C6A C7A H7A 119.1 . . ? C7A C8A C9A 120.6(3) . . ? C7A C8A H8A 119.7 . . ? C9A C8A H8A 119.7 . . ? C8A C9A C4A 118.8(3) . . ? C8A C9A H9A 120.6 . . ? C4A C9A H9A 120.6 . . ? C6A C10A H15A 109.5 . . ? C6A C10A H13A 109.5 . . ? H15A C10A H13A 109.5 . . ? C6A C10A H14A 109.5 . . ? H15A C10A H14A 109.5 . . ? H13A C10A H14A 109.5 . . ? C1B O1B H1B 109.5 . . ? C2B O2B H2B 109.5 . . ? C3B O3B C4B 117.0(2) . . ? C1A O1A H1A 109.5 . . ? C2A O2A H2A 109.5 . . ? C4A O3A C3A 117.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1B C1B C2B O2B 60.6(3) . . . . ? O1B C1B C2B C3B -56.7(3) . . . . ? O2B C2B C3B O3B -176.5(3) . . . . ? C1B C2B C3B O3B -56.2(3) . . . . ? C9B C4B C5B C6B -0.5(6) . . . . ? O3B C4B C5B C6B -179.3(3) . . . . ? C4B C5B C6B C7B 1.2(5) . . . . ? C4B C5B C6B C10B -179.3(4) . . . . ? C5B C6B C7B C8B -1.6(7) . . . . ? C10B C6B C7B C8B 179.0(4) . . . . ? C6B C7B C8B C9B 1.2(7) . . . . ? C5B C4B C9B C8B 0.1(6) . . . . ? O3B C4B C9B C8B 178.8(3) . . . . ? C7B C8B C9B C4B -0.4(6) . . . . ? O1A C1A C2A O2A -176.6(2) . . . . ? O1A C1A C2A C3A 57.9(3) . . . . ? O2A C2A C3A O3A -63.0(3) . . . . ? C1A C2A C3A O3A 61.3(4) . . . . ? O3A C4A C5A C6A -178.7(3) . . . . ? C9A C4A C5A C6A -0.7(4) . . . . ? C4A C5A C6A C7A 0.1(4) . . . . ? C4A C5A C6A C10A -178.9(3) . . . . ? C5A C6A C7A C8A 0.0(5) . . . . ? C10A C6A C7A C8A 179.0(4) . . . . ? C6A C7A C8A C9A 0.5(5) . . . . ? C7A C8A C9A C4A -1.1(5) . . . . ? O3A C4A C9A C8A 179.0(3) . . . . ? C5A C4A C9A C8A 1.3(4) . . . . ? C2B C3B O3B C4B -178.8(3) . . . . ? C5B C4B O3B C3B -176.4(3) . . . . ? C9B C4B O3B C3B 4.8(5) . . . . ? C5A C4A O3A C3A -177.0(3) . . . . ? C9A C4A O3A C3A 5.1(4) . . . . ? C2A C3A O3A C4A 173.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.132 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.028 # Attachment '- rac_2_modif.cif' data_bred_sm17 _database_code_depnum_ccdc_archive 'CCDC 826680' #TrackingRef '- rac_2_modif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 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 Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 12.3381(10) _cell_length_b 4.7318(3) _cell_length_c 32.877(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1919.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2657 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 26.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details ; G.M. Sheldrick (1998a). SADABS v.2.01, Bruker. Siemens Area Detector Absorption Correction Program. Bruker AXS. Madison. Wisconsin. USA ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 8574 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3529 _reflns_number_gt 2614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'APEX2 v2008.6-1 (Bruker AXS)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0807P)^2^+0.0310P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3529 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1447 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _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 C1A C 0.4436(3) 0.0612(9) 0.53510(11) 0.0499(9) Uani 1 1 d . . . H11A H 0.4174 -0.0571 0.5131 0.060 Uiso 1 1 calc R . . H12A H 0.4887 0.2078 0.5233 0.060 Uiso 1 1 calc R . . C1B C 0.6915(3) 0.4553(7) 0.67003(11) 0.0377(7) Uani 1 1 d . . . H11B H 0.6628 0.5635 0.6927 0.045 Uiso 1 1 calc R . . H12B H 0.7375 0.3078 0.6811 0.045 Uiso 1 1 calc R . . C2A C 0.3488(3) 0.1958(7) 0.55592(10) 0.0416(7) Uani 1 1 d . . . H21A H 0.3165 0.0540 0.5740 0.050 Uiso 1 1 calc R . . C2B C 0.5969(2) 0.3183(6) 0.64664(10) 0.0372(6) Uani 1 1 d . . . H21B H 0.5644 0.4632 0.6292 0.045 Uiso 1 1 calc R . . C3A C 0.2617(3) 0.2943(7) 0.52698(11) 0.0461(8) Uani 1 1 d . . . H31A H 0.2273 0.1326 0.5142 0.055 Uiso 1 1 calc R . . H32A H 0.2067 0.3989 0.5418 0.055 Uiso 1 1 calc R . . C3B C 0.5107(2) 0.2118(7) 0.67508(10) 0.0403(7) Uani 1 1 d . . . H31B H 0.4755 0.3704 0.6883 0.048 Uiso 1 1 calc R . . H32B H 0.4563 0.1088 0.6598 0.048 Uiso 1 1 calc R . . C4A C 0.2412(3) 0.5864(7) 0.46826(9) 0.0398(7) Uani 1 1 d . . . C4B C 0.4902(3) -0.0824(7) 0.73418(9) 0.0376(6) Uani 1 1 d . . . C5A C 0.2888(3) 0.7683(8) 0.44016(10) 0.0414(7) Uani 1 1 d . . . H5A H 0.3629 0.8039 0.4415 0.050 Uiso 1 1 calc R . . C5B C 0.5373(2) -0.2636(7) 0.76183(9) 0.0370(6) Uani 1 1 d . . . H5B H 0.6114 -0.2974 0.7603 0.044 Uiso 1 1 calc R . . C6A C 0.2269(3) 0.8970(7) 0.41017(10) 0.0434(7) Uani 1 1 d . . . C6B C 0.4773(3) -0.3970(7) 0.79190(9) 0.0410(7) Uani 1 1 d . . . C7A C 0.1162(3) 0.8407(8) 0.40891(12) 0.0549(9) Uani 1 1 d . . . H7A H 0.0731 0.9265 0.3893 0.066 Uiso 1 1 calc R . . C7B C 0.3664(3) -0.3407(8) 0.79333(12) 0.0538(9) Uani 1 1 d . . . H7B H 0.3238 -0.4276 0.8131 0.065 Uiso 1 1 calc R . . C8A C 0.0712(3) 0.6619(9) 0.43611(13) 0.0597(10) Uani 1 1 d . . . H8A H -0.0028 0.6270 0.4342 0.072 Uiso 1 1 calc R . . C8B C 0.3188(3) -0.1581(8) 0.76592(12) 0.0545(9) Uani 1 1 d . . . H8B H 0.2447 -0.1240 0.7672 0.065 Uiso 1 1 calc R . . C9A C 0.1292(4) 0.5263(8) 0.46693(13) 0.0509(11) Uani 1 1 d . . . H9A H 0.0962 0.4044 0.4854 0.061 Uiso 1 1 calc R . . C9B C 0.3813(4) -0.0243(7) 0.73629(13) 0.0435(9) Uani 1 1 d . . . H9B H 0.3497 0.1025 0.7182 0.052 Uiso 1 1 calc R . . C10A C 0.2796(4) 1.0931(9) 0.38068(12) 0.0572(10) Uani 1 1 d . . . H13A H 0.2858 1.2775 0.3927 0.086 Uiso 1 1 calc R . . H14A H 0.2365 1.1046 0.3564 0.086 Uiso 1 1 calc R . . H15A H 0.3505 1.0236 0.3740 0.086 Uiso 1 1 calc R . . C10B C 0.5288(3) -0.5972(8) 0.82139(12) 0.0522(9) Uani 1 1 d . . . H13B H 0.5332 -0.5095 0.8477 0.078 Uiso 1 1 calc R . . H14B H 0.6003 -0.6447 0.8122 0.078 Uiso 1 1 calc R . . H15B H 0.4858 -0.7658 0.8232 0.078 Uiso 1 1 calc R . . O1A O 0.5082(2) -0.1077(5) 0.56227(7) 0.0526(6) Uani 1 1 d . . . H1A H 0.4773 -0.2580 0.5667 0.079 Uiso 1 1 calc R . . O1B O 0.75432(17) 0.6340(5) 0.64531(7) 0.0471(6) Uani 1 1 d . . . H1B H 0.7184 0.7728 0.6389 0.071 Uiso 1 1 calc R . . O2A O 0.3895(2) 0.4216(5) 0.58100(8) 0.0492(6) Uani 1 1 d . . . H2A H 0.3429 0.4683 0.5975 0.074 Uiso 1 1 calc R . . O2B O 0.6397(2) 0.1040(5) 0.62126(8) 0.0492(6) Uani 1 1 d . . . H2B H 0.5968 0.0705 0.6028 0.074 Uiso 1 1 calc R . . O3A O 0.3102(2) 0.4738(5) 0.49613(8) 0.0455(7) Uani 1 1 d . . . O3B O 0.5576(2) 0.0299(5) 0.70520(8) 0.0438(6) 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 C1A 0.053(2) 0.0552(18) 0.041(2) -0.0020(18) 0.0023(17) -0.0008(18) C1B 0.0360(17) 0.0450(16) 0.0320(16) -0.0014(14) 0.0008(14) -0.0013(13) C2A 0.0489(18) 0.0405(16) 0.0353(15) 0.0004(14) 0.0052(13) -0.0082(14) C2B 0.0399(15) 0.0369(14) 0.0349(14) 0.0070(13) -0.0059(13) -0.0007(12) C3A 0.0448(17) 0.0480(18) 0.0455(17) 0.0039(15) 0.0059(15) -0.0068(15) C3B 0.0358(15) 0.0410(16) 0.0442(16) 0.0076(14) -0.0050(13) 0.0022(13) C4A 0.0396(18) 0.0431(16) 0.0368(16) -0.0062(15) 0.0013(13) -0.0004(16) C4B 0.0357(16) 0.0428(16) 0.0343(16) -0.0037(14) 0.0016(13) -0.0036(14) C5A 0.0423(16) 0.0431(18) 0.0388(16) -0.0046(13) -0.0041(14) -0.0029(13) C5B 0.0350(14) 0.0384(16) 0.0375(15) -0.0043(12) 0.0007(12) 0.0002(12) C6A 0.052(2) 0.0381(18) 0.0399(17) -0.0072(15) -0.0004(14) 0.0065(14) C6B 0.0526(19) 0.0378(18) 0.0326(15) -0.0031(13) 0.0040(14) 0.0023(14) C7A 0.051(2) 0.059(2) 0.055(2) 0.0063(18) -0.0149(17) 0.0035(17) C7B 0.052(2) 0.059(2) 0.051(2) 0.0019(17) 0.0157(16) -0.0074(17) C8A 0.0352(18) 0.071(3) 0.073(3) 0.003(2) -0.0101(17) 0.0009(17) C8B 0.0425(19) 0.060(2) 0.061(2) 0.0025(19) 0.0115(16) 0.0034(15) C9A 0.046(3) 0.059(2) 0.048(3) -0.0011(17) -0.002(2) -0.0019(16) C9B 0.038(2) 0.0450(17) 0.048(2) 0.0043(14) 0.0016(18) 0.0007(13) C10A 0.068(2) 0.060(2) 0.043(2) 0.0072(18) -0.0069(18) -0.007(2) C10B 0.070(2) 0.0404(18) 0.0459(18) 0.0020(16) 0.0023(17) 0.0008(17) O1A 0.0514(14) 0.0511(14) 0.0553(15) 0.0039(11) -0.0114(11) -0.0025(11) O1B 0.0441(12) 0.0453(13) 0.0521(13) 0.0049(11) 0.0043(11) -0.0040(9) O2A 0.0528(14) 0.0568(14) 0.0380(13) -0.0084(12) 0.0042(11) -0.0072(12) O2B 0.0592(15) 0.0485(13) 0.0397(13) -0.0019(11) -0.0021(10) 0.0062(12) O3A 0.0386(16) 0.0584(15) 0.0395(14) 0.0099(11) -0.0019(12) -0.0025(10) O3B 0.0318(14) 0.0577(14) 0.0419(14) 0.0175(11) 0.0021(12) 0.0036(10) _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 C1A O1A 1.440(5) . ? C1A C2A 1.497(5) . ? C1A H11A 0.9700 . ? C1A H12A 0.9700 . ? C1B O1B 1.405(4) . ? C1B C2B 1.541(5) . ? C1B H11B 0.9700 . ? C1B H12B 0.9700 . ? C2A O2A 1.440(4) . ? C2A C3A 1.509(5) . ? C2A H21A 0.9800 . ? C2B O2B 1.415(4) . ? C2B C3B 1.504(4) . ? C2B H21B 0.9800 . ? C3A O3A 1.452(4) . ? C3A H31A 0.9700 . ? C3A H32A 0.9700 . ? C3B O3B 1.434(4) . ? C3B H31B 0.9700 . ? C3B H32B 0.9700 . ? C4A O3A 1.359(4) . ? C4A C5A 1.393(5) . ? C4A C9A 1.411(6) . ? C4B O3B 1.371(4) . ? C4B C9B 1.374(6) . ? C4B C5B 1.378(4) . ? C5A C6A 1.388(5) . ? C5A H5A 0.9300 . ? C5B C6B 1.387(4) . ? C5B H5B 0.9300 . ? C6A C7A 1.392(5) . ? C6A C10A 1.491(5) . ? C6B C7B 1.396(5) . ? C6B C10B 1.497(5) . ? C7A C8A 1.351(6) . ? C7A H7A 0.9300 . ? C7B C8B 1.379(6) . ? C7B H7B 0.9300 . ? C8A C9A 1.397(6) . ? C8A H8A 0.9300 . ? C8B C9B 1.394(6) . ? C8B H8B 0.9300 . ? C9A H9A 0.9300 . ? C9B H9B 0.9300 . ? C10A H13A 0.9600 . ? C10A H14A 0.9600 . ? C10A H15A 0.9600 . ? C10B H13B 0.9600 . ? C10B H14B 0.9600 . ? C10B H15B 0.9600 . ? O1A H1A 0.8200 . ? O1B H1B 0.8200 . ? O2A H2A 0.8200 . ? O2B H2B 0.8200 . ? 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 O1A C1A C2A 112.7(3) . . ? O1A C1A H11A 109.1 . . ? C2A C1A H11A 109.1 . . ? O1A C1A H12A 109.1 . . ? C2A C1A H12A 109.1 . . ? H11A C1A H12A 107.8 . . ? O1B C1B C2B 112.5(3) . . ? O1B C1B H11B 109.1 . . ? C2B C1B H11B 109.1 . . ? O1B C1B H12B 109.1 . . ? C2B C1B H12B 109.1 . . ? H11B C1B H12B 107.8 . . ? O2A C2A C1A 107.8(3) . . ? O2A C2A C3A 112.3(3) . . ? C1A C2A C3A 113.5(3) . . ? O2A C2A H21A 107.6 . . ? C1A C2A H21A 107.6 . . ? C3A C2A H21A 107.6 . . ? O2B C2B C3B 113.0(3) . . ? O2B C2B C1B 108.2(3) . . ? C3B C2B C1B 111.5(3) . . ? O2B C2B H21B 108.0 . . ? C3B C2B H21B 108.0 . . ? C1B C2B H21B 108.0 . . ? O3A C3A C2A 109.1(3) . . ? O3A C3A H31A 109.9 . . ? C2A C3A H31A 109.9 . . ? O3A C3A H32A 109.9 . . ? C2A C3A H32A 109.9 . . ? H31A C3A H32A 108.3 . . ? O3B C3B C2B 110.2(2) . . ? O3B C3B H31B 109.6 . . ? C2B C3B H31B 109.6 . . ? O3B C3B H32B 109.6 . . ? C2B C3B H32B 109.6 . . ? H31B C3B H32B 108.1 . . ? O3A C4A C5A 115.1(3) . . ? O3A C4A C9A 123.7(3) . . ? C5A C4A C9A 121.1(3) . . ? O3B C4B C9B 123.4(3) . . ? O3B C4B C5B 116.4(3) . . ? C9B C4B C5B 120.2(3) . . ? C6A C5A C4A 120.6(3) . . ? C6A C5A H5A 119.7 . . ? C4A C5A H5A 119.7 . . ? C4B C5B C6B 121.9(3) . . ? C4B C5B H5B 119.0 . . ? C6B C5B H5B 119.0 . . ? C5A C6A C7A 118.5(3) . . ? C5A C6A C10A 119.6(3) . . ? C7A C6A C10A 121.9(3) . . ? C5B C6B C7B 117.4(3) . . ? C5B C6B C10B 121.6(3) . . ? C7B C6B C10B 121.0(3) . . ? C8A C7A C6A 120.3(3) . . ? C8A C7A H7A 119.9 . . ? C6A C7A H7A 119.9 . . ? C8B C7B C6B 121.0(3) . . ? C8B C7B H7B 119.5 . . ? C6B C7B H7B 119.5 . . ? C7A C8A C9A 123.9(3) . . ? C7A C8A H8A 118.1 . . ? C9A C8A H8A 118.1 . . ? C7B C8B C9B 120.4(3) . . ? C7B C8B H8B 119.8 . . ? C9B C8B H8B 119.8 . . ? C8A C9A C4A 115.6(4) . . ? C8A C9A H9A 122.2 . . ? C4A C9A H9A 122.2 . . ? C4B C9B C8B 119.0(3) . . ? C4B C9B H9B 120.5 . . ? C8B C9B H9B 120.5 . . ? C6A C10A H13A 109.5 . . ? C6A C10A H14A 109.5 . . ? H13A C10A H14A 109.5 . . ? C6A C10A H15A 109.5 . . ? H13A C10A H15A 109.5 . . ? H14A C10A H15A 109.5 . . ? C6B C10B H13B 109.5 . . ? C6B C10B H14B 109.5 . . ? H13B C10B H14B 109.5 . . ? C6B C10B H15B 109.5 . . ? H13B C10B H15B 109.5 . . ? H14B C10B H15B 109.5 . . ? C1A O1A H1A 109.5 . . ? C1B O1B H1B 109.5 . . ? C2A O2A H2A 109.5 . . ? C2B O2B H2B 109.5 . . ? C4A O3A C3A 116.2(3) . . ? C4B O3B C3B 117.9(3) . . ? 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 O1A C1A C2A O2A 73.2(4) . . . . ? O1A C1A C2A C3A -161.7(3) . . . . ? O1B C1B C2B O2B 74.5(3) . . . . ? O1B C1B C2B C3B -160.7(3) . . . . ? O2A C2A C3A O3A 69.8(3) . . . . ? C1A C2A C3A O3A -52.8(4) . . . . ? O2B C2B C3B O3B 69.1(3) . . . . ? C1B C2B C3B O3B -53.1(4) . . . . ? O3A C4A C5A C6A -179.9(3) . . . . ? C9A C4A C5A C6A 0.4(5) . . . . ? O3B C4B C5B C6B -178.2(3) . . . . ? C9B C4B C5B C6B 1.3(5) . . . . ? C4A C5A C6A C7A 0.2(5) . . . . ? C4A C5A C6A C10A 179.4(3) . . . . ? C4B C5B C6B C7B -0.1(5) . . . . ? C4B C5B C6B C10B 179.0(3) . . . . ? C5A C6A C7A C8A -0.8(5) . . . . ? C10A C6A C7A C8A 180.0(4) . . . . ? C5B C6B C7B C8B -0.3(5) . . . . ? C10B C6B C7B C8B -179.4(4) . . . . ? C6A C7A C8A C9A 0.8(6) . . . . ? C6B C7B C8B C9B -0.4(6) . . . . ? C7A C8A C9A C4A -0.2(6) . . . . ? O3A C4A C9A C8A 180.0(3) . . . . ? C5A C4A C9A C8A -0.4(5) . . . . ? O3B C4B C9B C8B 177.4(3) . . . . ? C5B C4B C9B C8B -2.0(5) . . . . ? C7B C8B C9B C4B 1.6(6) . . . . ? C5A C4A O3A C3A 177.1(3) . . . . ? C9A C4A O3A C3A -3.3(5) . . . . ? C2A C3A O3A C4A -178.2(3) . . . . ? C9B C4B O3B C3B -1.6(5) . . . . ? C5B C4B O3B C3B 177.9(3) . . . . ? C2B C3B O3B C4B 178.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 0.463 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.049