# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_osh104 _database_code_depnum_ccdc_archive 'CCDC 920658' #TrackingRef 'osh104.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 O3' _chemical_formula_sum 'C18 H18 O3' _chemical_formula_weight 282.32 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_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.4948(2) _cell_length_b 14.0951(2) _cell_length_c 7.5300(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.909(2) _cell_angle_gamma 90.00 _cell_volume 1421.88(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13681 _cell_measurement_theta_min 3.1336 _cell_measurement_theta_max 76.1054 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2158 _exptl_crystal_size_mid 0.1231 _exptl_crystal_size_min 0.0393 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; The crystal is a non-merohedral twin. The BASF refined to 0.2075(6), and the twin law is 1 0 0.4303 0 -1 0 0 0 1. The HKLF 5 card forces MERG 0, i.e. neither a number of unique reflections nor an internal R value can be determined. The figures given here are taken from an HKLF 4 file; in the integration which led to this file the twinning was ignored. Hence these figures are approximations. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22791 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 76.47 _reflns_number_total 2970 _reflns_number_gt 2787 _reflns_threshold_expression I>2\s(I) loop_ _diffrn_twin_id _diffrn_twin_ratio _diffrn_twin_reflns_isolated _diffrn_twin_reflns_overlapped 1 0.7722 13264 10055 2 0.2278 13162 10055 _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^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 5465 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.15788(6) 0.55790(6) 0.67469(11) 0.01664(17) Uani 1 1 d . . . C7 C 0.07458(7) 0.51721(6) 0.76496(12) 0.01857(17) Uani 1 1 d . . . O1 O 0.08387(5) 0.51510(5) 0.93405(8) 0.02050(14) Uani 1 1 d . . . H1O1 H 0.0286 0.5021 0.9687 0.031 Uiso 0.50 1 calc PR . . O2 O -0.00327(5) 0.48675(6) 0.67209(9) 0.02605(16) Uani 1 1 d . . . H1O2 H 0.0034 0.4915 0.5630 0.039 Uiso 0.50 1 calc PR . . C2 C 0.14003(6) 0.64577(6) 0.58907(11) 0.01646(17) Uani 1 1 d . . . O3 O 0.05149(5) 0.68688(5) 0.61678(9) 0.02039(14) Uani 1 1 d . . . C8 C 0.03264(7) 0.78161(7) 0.55359(13) 0.0233(2) Uani 1 1 d . . . H8A H 0.0874 0.8230 0.6033 0.035 Uiso 1 1 calc R . . H8B H -0.0302 0.8043 0.5915 0.035 Uiso 1 1 calc R . . H8C H 0.0278 0.7824 0.4227 0.035 Uiso 1 1 calc R . . C3 C 0.20741(7) 0.68158(6) 0.47996(11) 0.01769(17) Uani 1 1 d . . . H3 H 0.1934 0.7389 0.4156 0.021 Uiso 1 1 calc R . . C4 C 0.29599(6) 0.63226(6) 0.46612(12) 0.01847(17) Uani 1 1 d . . . C5 C 0.31818(6) 0.55143(7) 0.56928(12) 0.01910(18) Uani 1 1 d . . . H5 H 0.3831 0.5246 0.5758 0.023 Uiso 1 1 calc R . . C6 C 0.24652(7) 0.50880(6) 0.66382(12) 0.01769(17) Uani 1 1 d . . . C9 C 0.35706(7) 0.65324(7) 0.31472(13) 0.02234(19) Uani 1 1 d . . . H9A H 0.4287 0.6426 0.3559 0.027 Uiso 1 1 calc R . . H9B H 0.3483 0.7206 0.2790 0.027 Uiso 1 1 calc R . . C10 C 0.32401(7) 0.58786(7) 0.14892(12) 0.0234(2) Uani 1 1 d . . . H10A H 0.2535 0.6012 0.1033 0.028 Uiso 1 1 calc R . . H10B H 0.3654 0.6022 0.0523 0.028 Uiso 1 1 calc R . . C11 C 0.25690(7) 0.40501(7) 0.71137(13) 0.02185(19) Uani 1 1 d . . . H11A H 0.2171 0.3905 0.8103 0.026 Uiso 1 1 calc R . . H11B H 0.3277 0.3904 0.7526 0.026 Uiso 1 1 calc R . . C12 C 0.21977(7) 0.34193(7) 0.54453(14) 0.02367(19) Uani 1 1 d . . . H12A H 0.2250 0.2740 0.5780 0.028 Uiso 1 1 calc R . . H12B H 0.1489 0.3562 0.5036 0.028 Uiso 1 1 calc R . . C13 C 0.33510(7) 0.48451(7) 0.19907(12) 0.02284(19) Uani 1 1 d . . . C14 C 0.26163(7) 0.44166(7) 0.28852(13) 0.02156(19) Uani 1 1 d . . . H14 H 0.1962 0.4677 0.2760 0.026 Uiso 1 1 calc R . . C15 C 0.28234(7) 0.36159(7) 0.39568(13) 0.02281(19) Uani 1 1 d . . . C16 C 0.37319(8) 0.31505(7) 0.38906(14) 0.0266(2) Uani 1 1 d . . . H16 H 0.3875 0.2587 0.4565 0.032 Uiso 1 1 calc R . . C17 C 0.44281(8) 0.35075(8) 0.28426(15) 0.0294(2) Uani 1 1 d . . . H17 H 0.5023 0.3163 0.2734 0.035 Uiso 1 1 calc R . . C18 C 0.42553(7) 0.43670(8) 0.19546(13) 0.0275(2) Uani 1 1 d . . . H18 H 0.4756 0.4631 0.1318 0.033 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 C1 0.0198(4) 0.0178(4) 0.0125(4) -0.0005(3) 0.0030(3) -0.0032(3) C7 0.0225(4) 0.0159(4) 0.0183(4) 0.0024(3) 0.0067(3) 0.0008(3) O1 0.0232(3) 0.0256(3) 0.0133(3) 0.0003(2) 0.0049(2) -0.0040(3) O2 0.0240(3) 0.0388(4) 0.0157(3) 0.0016(3) 0.0035(3) -0.0122(3) C2 0.0192(4) 0.0166(4) 0.0137(4) -0.0025(3) 0.0025(3) -0.0014(3) O3 0.0242(3) 0.0173(3) 0.0212(3) 0.0024(2) 0.0091(2) 0.0024(2) C8 0.0299(5) 0.0179(4) 0.0225(4) 0.0023(3) 0.0047(4) 0.0042(3) C3 0.0227(4) 0.0159(4) 0.0144(4) 0.0003(3) 0.0017(3) -0.0037(3) C4 0.0189(4) 0.0213(4) 0.0156(4) -0.0011(3) 0.0033(3) -0.0061(3) C5 0.0160(4) 0.0243(4) 0.0168(4) -0.0008(3) 0.0012(3) -0.0023(3) C6 0.0201(4) 0.0188(4) 0.0137(4) 0.0008(3) 0.0006(3) -0.0014(3) C9 0.0195(4) 0.0279(5) 0.0206(4) 0.0034(3) 0.0065(3) -0.0050(3) C10 0.0222(4) 0.0322(5) 0.0167(4) 0.0032(4) 0.0057(3) 0.0010(4) C11 0.0243(4) 0.0205(4) 0.0207(4) 0.0043(3) 0.0027(3) 0.0022(3) C12 0.0248(4) 0.0179(4) 0.0278(5) 0.0018(3) 0.0010(4) 0.0004(3) C13 0.0217(4) 0.0312(5) 0.0154(4) -0.0032(4) 0.0012(3) 0.0021(4) C14 0.0188(4) 0.0259(5) 0.0193(4) -0.0032(4) -0.0008(3) 0.0017(3) C15 0.0225(4) 0.0227(4) 0.0223(4) -0.0051(4) -0.0010(3) 0.0003(3) C16 0.0280(5) 0.0238(5) 0.0263(5) -0.0067(4) -0.0037(4) 0.0056(4) C17 0.0245(4) 0.0349(6) 0.0279(5) -0.0100(4) -0.0007(4) 0.0096(4) C18 0.0227(4) 0.0393(6) 0.0207(4) -0.0059(4) 0.0042(3) 0.0040(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 C1 C6 1.3930(12) . ? C1 C2 1.4037(12) . ? C1 C7 1.4962(11) . ? C7 O1 1.2646(11) . ? C7 O2 1.2650(12) . ? O1 H1O1 0.8400 . ? O2 H1O2 0.8400 . ? C2 O3 1.3664(10) . ? C2 C3 1.3915(12) . ? O3 C8 1.4300(10) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C3 C4 1.3975(12) . ? C3 H3 0.9500 . ? C4 C5 1.3911(13) . ? C4 C9 1.5141(11) . ? C5 C6 1.4030(12) . ? C5 H5 0.9500 . ? C6 C11 1.5085(12) . ? C9 C10 1.5725(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C13 1.5077(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5712(13) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C15 1.5080(14) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.3973(13) . ? C13 C14 1.4008(14) . ? C14 C15 1.3959(14) . ? C14 H14 0.9500 . ? C15 C16 1.3965(13) . ? C16 C17 1.3918(16) . ? C16 H16 0.9500 . ? C17 C18 1.3897(16) . ? C17 H17 0.9500 . ? C18 H18 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 C6 C1 C2 120.83(8) . . ? C6 C1 C7 122.25(8) . . ? C2 C1 C7 116.76(8) . . ? O1 C7 O2 121.58(8) . . ? O1 C7 C1 118.52(8) . . ? O2 C7 C1 119.89(8) . . ? C7 O1 H1O1 109.5 . . ? C7 O2 H1O2 109.5 . . ? O3 C2 C3 125.59(8) . . ? O3 C2 C1 114.13(8) . . ? C3 C2 C1 120.20(8) . . ? C2 O3 C8 117.96(7) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C3 C4 119.28(8) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.63(8) . . ? C5 C4 C9 118.71(8) . . ? C3 C4 C9 120.46(8) . . ? C4 C5 C6 121.26(8) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.79(8) . . ? C1 C6 C11 121.58(8) . . ? C5 C6 C11 119.07(8) . . ? C4 C9 C10 110.80(7) . . ? C4 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C13 C10 C9 110.93(8) . . ? C13 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C13 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C6 C11 C12 110.33(8) . . ? C6 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? C6 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C15 C12 C11 109.70(8) . . ? C15 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C15 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C18 C13 C14 118.14(10) . . ? C18 C13 C10 121.45(9) . . ? C14 C13 C10 118.84(9) . . ? C15 C14 C13 121.50(9) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 118.34(9) . . ? C14 C15 C12 119.15(9) . . ? C16 C15 C12 120.84(9) . . ? C17 C16 C15 120.38(10) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 120.16(9) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 120.49(10) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? 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 C6 C1 C7 O1 75.25(11) . . . . ? C2 C1 C7 O1 -109.27(10) . . . . ? C6 C1 C7 O2 -105.42(11) . . . . ? C2 C1 C7 O2 70.06(11) . . . . ? C6 C1 C2 O3 -177.87(8) . . . . ? C7 C1 C2 O3 6.58(11) . . . . ? C6 C1 C2 C3 5.17(13) . . . . ? C7 C1 C2 C3 -170.38(8) . . . . ? C3 C2 O3 C8 -10.90(12) . . . . ? C1 C2 O3 C8 172.33(7) . . . . ? O3 C2 C3 C4 179.20(8) . . . . ? C1 C2 C3 C4 -4.21(12) . . . . ? C2 C3 C4 C5 -3.77(13) . . . . ? C2 C3 C4 C9 163.54(8) . . . . ? C3 C4 C5 C6 11.09(13) . . . . ? C9 C4 C5 C6 -156.44(8) . . . . ? C2 C1 C6 C5 1.87(12) . . . . ? C7 C1 C6 C5 177.17(8) . . . . ? C2 C1 C6 C11 -163.71(8) . . . . ? C7 C1 C6 C11 11.59(13) . . . . ? C4 C5 C6 C1 -10.02(13) . . . . ? C4 C5 C6 C11 155.94(9) . . . . ? C5 C4 C9 C10 76.90(10) . . . . ? C3 C4 C9 C10 -90.52(10) . . . . ? C4 C9 C10 C13 -58.40(10) . . . . ? C1 C6 C11 C12 86.60(10) . . . . ? C5 C6 C11 C12 -78.80(10) . . . . ? C6 C11 C12 C15 61.04(10) . . . . ? C9 C10 C13 C18 -86.17(10) . . . . ? C9 C10 C13 C14 79.31(10) . . . . ? C18 C13 C14 C15 10.25(14) . . . . ? C10 C13 C14 C15 -155.71(9) . . . . ? C13 C14 C15 C16 -10.55(14) . . . . ? C13 C14 C15 C12 154.87(9) . . . . ? C11 C12 C15 C14 -80.39(10) . . . . ? C11 C12 C15 C16 84.65(11) . . . . ? C14 C15 C16 C17 2.97(14) . . . . ? C12 C15 C16 C17 -162.19(9) . . . . ? C15 C16 C17 C18 4.64(15) . . . . ? C16 C17 C18 C13 -4.94(15) . . . . ? C14 C13 C18 C17 -2.37(14) . . . . ? C10 C13 C18 C17 163.20(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O2 O2 0.84 1.80 2.6305(14) 171.9 3_566 O1 H1O1 O1 0.84 1.78 2.6139(13) 172.4 3_567 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 76.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.253 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.052 data_osh105 _database_code_depnum_ccdc_archive 'CCDC 920659' #TrackingRef 'osh105.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 O3' _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.38 _chemical_absolute_configuration ad 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_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.15436(7) _cell_length_b 8.76221(7) _cell_length_c 12.1310(1) _cell_angle_alpha 90.00 _cell_angle_beta 107.081(1) _cell_angle_gamma 90.00 _cell_volume 828.530(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12925 _cell_measurement_theta_min 3.8088 _cell_measurement_theta_max 76.4317 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3840 _exptl_crystal_size_mid 0.2026 _exptl_crystal_size_min 0.1554 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; 1603 Friedel pairs were measured. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16971 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 76.63 _reflns_number_total 3445 _reflns_number_gt 3405 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.1148P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(13) _refine_ls_number_reflns 3445 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.33507(13) 0.85646(11) 0.14170(9) 0.0167(2) Uani 1 1 d . . . C7 C 0.18984(13) 0.74676(13) 0.09623(9) 0.0177(2) Uani 1 1 d . . . O1 O 0.20689(10) 0.61245(10) 0.08161(9) 0.0316(2) Uani 1 1 d . . . O2 O 0.03947(9) 0.81817(9) 0.07338(7) 0.02132(17) Uani 1 1 d . . . C8 C -0.11392(13) 0.72826(14) 0.01899(10) 0.0226(2) Uani 1 1 d . . . H8A H -0.2131 0.7707 0.0401 0.027 Uiso 1 1 calc R . . H8B H -0.0965 0.6216 0.0469 0.027 Uiso 1 1 calc R . . C9 C -0.15023(15) 0.73133(14) -0.11006(10) 0.0239(2) Uani 1 1 d . . . H9A H -0.1514 0.8373 -0.1362 0.036 Uiso 1 1 calc R . . H9B H -0.2621 0.6843 -0.1464 0.036 Uiso 1 1 calc R . . H9C H -0.0608 0.6744 -0.1316 0.036 Uiso 1 1 calc R . . C2 C 0.40973(14) 0.92398(12) 0.06293(9) 0.0168(2) Uani 1 1 d . . . O3 O 0.33106(10) 0.88980(9) -0.05025(6) 0.01983(17) Uani 1 1 d . . . C10 C 0.40216(15) 0.95714(14) -0.13369(10) 0.0236(2) Uani 1 1 d . . . H10A H 0.4091 1.0681 -0.1229 0.035 Uiso 1 1 calc R . . H10B H 0.3287 0.9335 -0.2115 0.035 Uiso 1 1 calc R . . H10C H 0.5173 0.9159 -0.1238 0.035 Uiso 1 1 calc R . . C3 C 0.55601(13) 1.01453(12) 0.10203(9) 0.0175(2) Uani 1 1 d . . . H3 H 0.6128 1.0520 0.0495 0.021 Uiso 1 1 calc R . . C4 C 0.61826(13) 1.04958(12) 0.21954(9) 0.0171(2) Uani 1 1 d . . . C5 C 0.52912(13) 0.99751(12) 0.29391(9) 0.0172(2) Uani 1 1 d . . . H5 H 0.5590 1.0356 0.3706 0.021 Uiso 1 1 calc R . . C6 C 0.39681(13) 0.89076(12) 0.25884(9) 0.0172(2) Uani 1 1 d . . . C11 C 0.79620(13) 1.11485(13) 0.26949(9) 0.0194(2) Uani 1 1 d . . . H11A H 0.7979 1.1824 0.3352 0.023 Uiso 1 1 calc R . . H11B H 0.8269 1.1768 0.2102 0.023 Uiso 1 1 calc R . . C12 C 0.93113(13) 0.98373(13) 0.31141(10) 0.0208(2) Uani 1 1 d . . . H12A H 0.9319 0.9177 0.2454 0.025 Uiso 1 1 calc R . . H12B H 1.0471 1.0282 0.3431 0.025 Uiso 1 1 calc R . . C13 C 0.35195(13) 0.79448(14) 0.34917(9) 0.0209(2) Uani 1 1 d . . . H13A H 0.2365 0.7494 0.3165 0.025 Uiso 1 1 calc R . . H13B H 0.3497 0.8592 0.4156 0.025 Uiso 1 1 calc R . . C14 C 0.48816(15) 0.66370(13) 0.39081(10) 0.0230(2) Uani 1 1 d . . . H14A H 0.4567 0.5998 0.4488 0.028 Uiso 1 1 calc R . . H14B H 0.4885 0.5978 0.3246 0.028 Uiso 1 1 calc R . . C15 C 0.88682(13) 0.88969(12) 0.40302(9) 0.0199(2) Uani 1 1 d . . . C16 C 0.94048(14) 0.93385(14) 0.51872(10) 0.0242(2) Uani 1 1 d . . . H16 H 1.0307 1.0059 0.5445 0.029 Uiso 1 1 calc R . . C17 C 0.86217(16) 0.87263(15) 0.59632(10) 0.0273(3) Uani 1 1 d . . . H17 H 0.9050 0.8972 0.6759 0.033 Uiso 1 1 calc R . . C18 C 0.72166(15) 0.77577(14) 0.55827(10) 0.0250(3) Uani 1 1 d . . . H18 H 0.6639 0.7406 0.6110 0.030 Uiso 1 1 calc R . . C19 C 0.66519(14) 0.73000(13) 0.44306(10) 0.0213(2) Uani 1 1 d . . . C20 C 0.75832(14) 0.77914(12) 0.36922(10) 0.0197(2) Uani 1 1 d . . . H20 H 0.7334 0.7362 0.2942 0.024 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 C1 0.0144(4) 0.0151(5) 0.0202(5) 0.0009(4) 0.0044(4) 0.0012(4) C7 0.0178(5) 0.0187(5) 0.0175(5) 0.0013(4) 0.0067(4) 0.0002(4) O1 0.0232(4) 0.0175(4) 0.0513(6) -0.0014(4) 0.0067(4) -0.0001(3) O2 0.0151(3) 0.0208(4) 0.0265(4) -0.0041(3) 0.0038(3) -0.0002(3) C8 0.0144(5) 0.0284(6) 0.0245(5) -0.0033(5) 0.0048(4) -0.0038(4) C9 0.0227(5) 0.0246(5) 0.0240(5) -0.0052(4) 0.0061(4) -0.0044(4) C2 0.0178(5) 0.0159(5) 0.0160(5) 0.0004(4) 0.0040(4) 0.0026(4) O3 0.0217(3) 0.0227(4) 0.0146(3) -0.0005(3) 0.0045(3) -0.0043(3) C10 0.0279(6) 0.0266(6) 0.0164(5) 0.0011(4) 0.0065(4) -0.0047(4) C3 0.0179(5) 0.0166(5) 0.0182(5) 0.0026(4) 0.0058(4) 0.0007(4) C4 0.0166(5) 0.0140(5) 0.0196(5) 0.0015(4) 0.0036(4) 0.0012(4) C5 0.0176(5) 0.0178(5) 0.0158(4) -0.0004(4) 0.0044(4) 0.0033(4) C6 0.0158(4) 0.0185(5) 0.0181(5) 0.0017(4) 0.0063(4) 0.0030(4) C11 0.0178(5) 0.0186(5) 0.0208(5) 0.0004(4) 0.0041(4) -0.0020(4) C12 0.0155(5) 0.0229(6) 0.0234(5) -0.0006(4) 0.0048(4) -0.0004(4) C13 0.0197(5) 0.0248(6) 0.0193(5) 0.0015(4) 0.0073(4) -0.0020(4) C14 0.0264(6) 0.0211(5) 0.0221(5) 0.0055(4) 0.0083(4) -0.0011(5) C15 0.0168(5) 0.0193(5) 0.0220(5) 0.0019(4) 0.0033(4) 0.0043(4) C16 0.0199(5) 0.0258(6) 0.0230(5) 0.0006(4) 0.0001(4) 0.0005(4) C17 0.0293(6) 0.0304(6) 0.0181(5) 0.0028(5) 0.0006(4) 0.0032(5) C18 0.0269(5) 0.0268(6) 0.0204(5) 0.0074(4) 0.0057(4) 0.0029(5) C19 0.0235(5) 0.0172(5) 0.0224(5) 0.0046(4) 0.0055(4) 0.0032(4) C20 0.0205(5) 0.0171(5) 0.0205(5) 0.0007(4) 0.0042(4) 0.0037(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 C1 C6 1.3938(14) . ? C1 C2 1.4056(14) . ? C1 C7 1.4989(14) . ? C7 O1 1.2043(14) . ? C7 O2 1.3312(13) . ? O2 C8 1.4615(12) . ? C8 C9 1.5056(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C2 O3 1.3670(13) . ? C2 C3 1.3946(15) . ? O3 C10 1.4332(13) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C3 C4 1.3997(14) . ? C3 H3 0.9500 . ? C4 C5 1.3913(15) . ? C4 C11 1.5109(14) . ? C5 C6 1.3965(14) . ? C5 H5 0.9500 . ? C6 C13 1.5107(14) . ? C11 C12 1.5687(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C15 1.5101(15) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5724(15) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.5118(15) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.3966(16) . ? C15 C20 1.3972(15) . ? C16 C17 1.3909(18) . ? C16 H16 0.9500 . ? C17 C18 1.3912(18) . ? C17 H17 0.9500 . ? C18 C19 1.3958(16) . ? C18 H18 0.9500 . ? C19 C20 1.4015(16) . ? C20 H20 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 C6 C1 C2 120.23(9) . . ? C6 C1 C7 121.54(9) . . ? C2 C1 C7 118.22(9) . . ? O1 C7 O2 124.59(10) . . ? O1 C7 C1 124.61(10) . . ? O2 C7 C1 110.79(9) . . ? C7 O2 C8 117.03(9) . . ? O2 C8 C9 109.92(9) . . ? O2 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? O2 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C2 C3 124.64(9) . . ? O3 C2 C1 114.92(9) . . ? C3 C2 C1 120.41(9) . . ? C2 O3 C10 116.83(8) . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C3 C4 119.30(10) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.09(10) . . ? C5 C4 C11 119.15(9) . . ? C3 C4 C11 120.65(9) . . ? C4 C5 C6 121.74(9) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 118.06(9) . . ? C1 C6 C13 121.82(9) . . ? C5 C6 C13 118.88(9) . . ? C4 C11 C12 110.63(9) . . ? C4 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C15 C12 C11 109.97(8) . . ? C15 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C15 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C6 C13 C14 109.95(8) . . ? C6 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C6 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C19 C14 C13 110.61(9) . . ? C19 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C19 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C20 118.27(10) . . ? C16 C15 C12 121.09(10) . . ? C20 C15 C12 118.90(9) . . ? C17 C16 C15 120.18(11) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.52(11) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 120.32(11) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 118.06(11) . . ? C18 C19 C14 121.59(10) . . ? C20 C19 C14 118.69(10) . . ? C15 C20 C19 121.73(10) . . ? C15 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? 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 C6 C1 C7 O1 -93.35(14) . . . . ? C2 C1 C7 O1 86.10(14) . . . . ? C6 C1 C7 O2 87.13(12) . . . . ? C2 C1 C7 O2 -93.42(11) . . . . ? O1 C7 O2 C8 -4.66(16) . . . . ? C1 C7 O2 C8 174.86(8) . . . . ? C7 O2 C8 C9 -87.12(12) . . . . ? C6 C1 C2 O3 -175.76(9) . . . . ? C7 C1 C2 O3 4.78(14) . . . . ? C6 C1 C2 C3 6.00(15) . . . . ? C7 C1 C2 C3 -173.47(9) . . . . ? C3 C2 O3 C10 -2.29(15) . . . . ? C1 C2 O3 C10 179.54(9) . . . . ? O3 C2 C3 C4 175.85(10) . . . . ? C1 C2 C3 C4 -6.08(15) . . . . ? C2 C3 C4 C5 -2.21(15) . . . . ? C2 C3 C4 C11 165.67(9) . . . . ? C3 C4 C5 C6 10.92(15) . . . . ? C11 C4 C5 C6 -157.14(10) . . . . ? C2 C1 C6 C5 2.40(15) . . . . ? C7 C1 C6 C5 -178.15(9) . . . . ? C2 C1 C6 C13 -164.77(10) . . . . ? C7 C1 C6 C13 14.68(15) . . . . ? C4 C5 C6 C1 -10.95(15) . . . . ? C4 C5 C6 C13 156.60(10) . . . . ? C5 C4 C11 C12 77.88(12) . . . . ? C3 C4 C11 C12 -89.99(12) . . . . ? C4 C11 C12 C15 -59.92(11) . . . . ? C1 C6 C13 C14 90.00(11) . . . . ? C5 C6 C13 C14 -77.07(12) . . . . ? C6 C13 C14 C19 60.33(12) . . . . ? C11 C12 C15 C16 -84.97(12) . . . . ? C11 C12 C15 C20 79.74(12) . . . . ? C20 C15 C16 C17 -2.43(16) . . . . ? C12 C15 C16 C17 162.37(10) . . . . ? C15 C16 C17 C18 -4.78(18) . . . . ? C16 C17 C18 C19 4.65(18) . . . . ? C17 C18 C19 C20 2.66(17) . . . . ? C17 C18 C19 C14 -162.43(11) . . . . ? C13 C14 C19 C18 84.39(12) . . . . ? C13 C14 C19 C20 -80.61(13) . . . . ? C16 C15 C20 C19 10.01(16) . . . . ? C12 C15 C20 C19 -155.13(10) . . . . ? C18 C19 C20 C15 -10.12(16) . . . . ? C14 C19 C20 C15 155.41(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 76.63 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.193 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.036