# 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_1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 O5' _chemical_formula_sum 'C9 H14 O5' _chemical_formula_weight 202.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2/a _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 11.960(3) _cell_length_b 10.526(2) _cell_length_c 15.425(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.368(2) _cell_angle_gamma 90.00 _cell_volume 1903.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4150 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.904 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10496 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.62 _reflns_number_total 2880 _reflns_number_gt 2143 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0698P)^2^+0.4214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2880 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.07409(9) 0.75444(10) 0.09086(8) 0.0230(2) Uani 1 1 d . . . O1 O 0.19412(7) 0.75004(7) 0.12348(6) 0.0270(2) Uani 1 1 d . . . C2 C 0.23686(10) 0.87787(11) 0.12049(9) 0.0282(3) Uani 1 1 d . . . H2A H 0.2889 0.8845 0.0781 0.034 Uiso 1 1 calc R . . H2B H 0.2778 0.9056 0.1796 0.034 Uiso 1 1 calc R . . C3 C 0.12898(9) 0.95663(11) 0.08975(7) 0.0253(2) Uani 1 1 d . . . H3 H 0.1435 1.0305 0.0527 0.030 Uiso 1 1 calc R . . O2 O 0.05516(7) 0.86361(7) 0.03817(5) 0.02311(19) Uani 1 1 d . . . C4 C 0.07264(10) 0.99794(11) 0.16467(8) 0.0297(3) Uani 1 1 d . . . H4A H -0.0026 1.0361 0.1402 0.036 Uiso 1 1 calc R . . H4B H 0.1202 1.0633 0.2006 0.036 Uiso 1 1 calc R . . C5 C 0.05700(11) 0.88439(12) 0.22352(8) 0.0312(3) Uani 1 1 d . . . H5A H 0.0018 0.9077 0.2610 0.037 Uiso 1 1 calc R . . H5B H 0.1308 0.8654 0.2632 0.037 Uiso 1 1 calc R . . C6 C 0.01415(10) 0.76379(11) 0.17017(8) 0.0254(2) Uani 1 1 d . . . H6 H 0.0366 0.6882 0.2090 0.031 Uiso 1 1 calc R . . O3 O 0.03734(7) 0.64769(7) 0.04262(6) 0.0275(2) Uani 1 1 d . . . C7 C 0.07530(11) 0.63735(12) -0.04022(9) 0.0315(3) Uani 1 1 d . . . H7A H 0.0385 0.7034 -0.0809 0.047 Uiso 1 1 calc R . . H7B H 0.0549 0.5535 -0.0662 0.047 Uiso 1 1 calc R . . H7C H 0.1583 0.6482 -0.0299 0.047 Uiso 1 1 calc R . . C8 C -0.11395(10) 0.76334(12) 0.14111(8) 0.0290(3) Uani 1 1 d . . . O4 O -0.17237(9) 0.85569(10) 0.12557(10) 0.0597(4) Uani 1 1 d . . . O5 O -0.15661(7) 0.64583(9) 0.13722(7) 0.0348(2) Uani 1 1 d . . . C9 C -0.27874(12) 0.63515(15) 0.11569(11) 0.0436(4) Uani 1 1 d . . . H9A H -0.3117 0.6767 0.1617 0.065 Uiso 1 1 calc R . . H9B H -0.3003 0.5452 0.1121 0.065 Uiso 1 1 calc R . . H9C H -0.3075 0.6762 0.0586 0.065 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 0.0202(5) 0.0201(5) 0.0297(6) 0.0014(4) 0.0076(4) 0.0011(4) O1 0.0185(4) 0.0237(4) 0.0392(5) 0.0024(3) 0.0067(3) 0.0014(3) C2 0.0214(5) 0.0253(5) 0.0386(6) -0.0011(4) 0.0073(5) -0.0022(4) C3 0.0241(5) 0.0208(5) 0.0313(6) -0.0014(4) 0.0063(4) -0.0025(4) O2 0.0232(4) 0.0200(4) 0.0265(4) 0.0009(3) 0.0057(3) -0.0014(3) C4 0.0292(6) 0.0260(6) 0.0348(6) -0.0055(4) 0.0083(5) 0.0011(4) C5 0.0316(6) 0.0359(6) 0.0278(6) -0.0033(5) 0.0097(5) -0.0001(5) C6 0.0230(5) 0.0265(5) 0.0284(6) 0.0038(4) 0.0090(4) 0.0024(4) O3 0.0274(4) 0.0221(4) 0.0366(5) -0.0047(3) 0.0150(3) -0.0041(3) C7 0.0315(6) 0.0286(6) 0.0388(7) -0.0085(5) 0.0178(5) -0.0060(5) C8 0.0248(6) 0.0317(6) 0.0330(6) 0.0025(4) 0.0119(5) 0.0021(4) O4 0.0280(5) 0.0360(6) 0.1150(11) 0.0062(6) 0.0139(6) 0.0088(4) O5 0.0256(4) 0.0337(5) 0.0461(6) 0.0032(4) 0.0097(4) -0.0043(3) C9 0.0265(6) 0.0567(9) 0.0495(8) -0.0018(7) 0.0117(6) -0.0104(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.3713(13) . ? C1 O2 1.3999(13) . ? C1 O1 1.4253(14) . ? C1 C6 1.5381(17) . ? O1 C2 1.4434(13) . ? C2 C3 1.5284(16) . ? C3 O2 1.4471(13) . ? C3 C4 1.5118(16) . ? C4 C5 1.5345(18) . ? C5 C6 1.5444(17) . ? C6 C8 1.5091(16) . ? O3 C7 1.4421(15) . ? C8 O4 1.1935(16) . ? C8 O5 1.3348(15) . ? O5 C9 1.4371(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 C1 O2 111.09(10) . . ? O3 C1 O1 110.96(8) . . ? O2 C1 O1 105.55(8) . . ? O3 C1 C6 109.52(9) . . ? O2 C1 C6 111.21(9) . . ? O1 C1 C6 108.43(10) . . ? C1 O1 C2 107.27(8) . . ? O1 C2 C3 103.47(9) . . ? O2 C3 C4 107.41(9) . . ? O2 C3 C2 100.94(9) . . ? C4 C3 C2 113.26(10) . . ? C1 O2 C3 103.00(8) . . ? C3 C4 C5 110.67(10) . . ? C4 C5 C6 113.04(10) . . ? C8 C6 C1 111.63(10) . . ? C8 C6 C5 111.82(10) . . ? C1 C6 C5 108.59(9) . . ? C1 O3 C7 114.79(9) . . ? O4 C8 O5 122.84(12) . . ? O4 C8 C6 125.23(12) . . ? O5 C8 C6 111.90(10) . . ? C8 O5 C9 116.42(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 O3 C1 O1 C2 143.63(10) . . . . ? O2 C1 O1 C2 23.20(11) . . . . ? C6 C1 O1 C2 -96.04(10) . . . . ? C1 O1 C2 C3 4.07(12) . . . . ? O1 C2 C3 O2 -28.51(11) . . . . ? O1 C2 C3 C4 86.00(11) . . . . ? O3 C1 O2 C3 -162.56(9) . . . . ? O1 C1 O2 C3 -42.21(10) . . . . ? C6 C1 O2 C3 75.17(11) . . . . ? C4 C3 O2 C1 -75.70(10) . . . . ? C2 C3 O2 C1 43.13(10) . . . . ? O2 C3 C4 C5 60.49(12) . . . . ? C2 C3 C4 C5 -50.08(13) . . . . ? C3 C4 C5 C6 -42.90(14) . . . . ? O3 C1 C6 C8 -56.39(12) . . . . ? O2 C1 C6 C8 66.78(12) . . . . ? O1 C1 C6 C8 -177.60(9) . . . . ? O3 C1 C6 C5 179.89(9) . . . . ? O2 C1 C6 C5 -56.95(12) . . . . ? O1 C1 C6 C5 58.67(11) . . . . ? C4 C5 C6 C8 -84.38(12) . . . . ? C4 C5 C6 C1 39.23(13) . . . . ? O2 C1 O3 C7 48.60(13) . . . . ? O1 C1 O3 C7 -68.49(12) . . . . ? C6 C1 O3 C7 171.83(9) . . . . ? C1 C6 C8 O4 -91.96(16) . . . . ? C5 C6 C8 O4 29.92(18) . . . . ? C1 C6 C8 O5 90.09(12) . . . . ? C5 C6 C8 O5 -148.03(11) . . . . ? O4 C8 O5 C9 -1.9(2) . . . . ? C6 C8 O5 C9 176.13(11) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.284 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.054 _iucr_refine_instruction_details ; TITL 1a in I2/a CELL 0.71073 11.960 10.526 15.425 90.000 101.368 90.000 ZERR 8.00 0.003 0.002 0.004 0.000 0.002 0.000 LATT 2 SYMM 0.5-X, Y, -Z SFAC C H O UNIT 72 112 40 TEMP -123 SIZE 0.34 0.34 0.89 ACTA 58 CONF WPDB -1 L.S. 6 BOND FMAP 2 PLAN 10 REM EXTI 0.0011(8) insig. WGHT 0.069800 0.421400 FVAR 0.13220 C1 1 0.074089 0.754437 0.090859 11.00000 0.02021 0.02009 = 0.02967 0.00144 0.00757 0.00112 O1 3 0.194124 0.750036 0.123480 11.00000 0.01848 0.02366 = 0.03922 0.00236 0.00674 0.00137 C2 1 0.236862 0.877874 0.120494 11.00000 0.02143 0.02532 = 0.03855 -0.00108 0.00733 -0.00221 AFIX 23 H2A 2 0.288934 0.884492 0.078133 11.00000 -1.20000 H2B 2 0.277763 0.905622 0.179605 11.00000 -1.20000 AFIX 0 C3 1 0.128976 0.956635 0.089745 11.00000 0.02410 0.02076 = 0.03131 -0.00142 0.00629 -0.00249 AFIX 13 H3 2 0.143520 1.030451 0.052683 11.00000 -1.20000 AFIX 0 O2 3 0.055158 0.863608 0.038174 11.00000 0.02318 0.01996 = 0.02650 0.00088 0.00566 -0.00137 C4 1 0.072641 0.997939 0.164668 11.00000 0.02923 0.02595 = 0.03478 -0.00555 0.00835 0.00108 AFIX 23 H4A 2 -0.002614 1.036119 0.140202 11.00000 -1.20000 H4B 2 0.120227 1.063315 0.200585 11.00000 -1.20000 AFIX 0 C5 1 0.056999 0.884392 0.223522 11.00000 0.03157 0.03591 = 0.02777 -0.00327 0.00971 -0.00013 AFIX 23 H5A 2 0.001785 0.907705 0.260959 11.00000 -1.20000 H5B 2 0.130776 0.865406 0.263191 11.00000 -1.20000 AFIX 0 C6 1 0.014150 0.763794 0.170167 11.00000 0.02297 0.02650 = 0.02844 0.00380 0.00898 0.00241 AFIX 13 H6 2 0.036640 0.688234 0.208987 11.00000 -1.20000 AFIX 0 O3 3 0.037336 0.647687 0.042623 11.00000 0.02735 0.02205 = 0.03663 -0.00466 0.01499 -0.00415 C7 1 0.075304 0.637348 -0.040218 11.00000 0.03150 0.02862 = 0.03882 -0.00847 0.01781 -0.00601 AFIX 137 H7A 2 0.038540 0.703358 -0.080857 11.00000 -1.50000 H7B 2 0.054917 0.553482 -0.066160 11.00000 -1.50000 H7C 2 0.158256 0.648178 -0.029934 11.00000 -1.50000 AFIX 0 C8 1 -0.113952 0.763339 0.141110 11.00000 0.02476 0.03169 = 0.03295 0.00246 0.01189 0.00210 O4 3 -0.172370 0.855685 0.125573 11.00000 0.02797 0.03604 = 0.11498 0.00619 0.01394 0.00882 O5 3 -0.156611 0.645830 0.137215 11.00000 0.02561 0.03367 = 0.04608 0.00323 0.00969 -0.00432 C9 1 -0.278739 0.635148 0.115693 11.00000 0.02653 0.05668 = 0.04946 -0.00175 0.01170 -0.01041 AFIX 137 H9A 2 -0.311694 0.676723 0.161685 11.00000 -1.50000 H9B 2 -0.300346 0.545211 0.112082 11.00000 -1.50000 H9C 2 -0.307460 0.676225 0.058634 11.00000 -1.50000 HKLF 4 REM 1a in I2/a REM R1 = 0.0438 for 2143 Fo > 4sig(Fo) and 0.0587 for all 2880 data REM 129 parameters refined using 0 restraints END WGHT 0.0698 0.4214 REM Highest difference peak 0.284, deepest hole -0.271, 1-sigma level 0.054 Q1 1 0.2137 0.7487 0.1804 11.00000 0.05 0.28 Q2 1 0.0177 0.8670 -0.0194 11.00000 0.05 0.28 Q3 1 0.1853 0.9198 0.1062 11.00000 0.05 0.27 Q4 1 -0.3034 0.6287 0.0611 11.00000 0.05 0.24 Q5 1 0.0339 0.7575 0.1296 11.00000 0.05 0.24 Q6 1 -0.1699 0.8316 0.0944 11.00000 0.05 0.24 Q7 1 0.2669 0.8742 0.1788 11.00000 0.05 0.24 Q8 1 -0.1209 0.6333 0.1993 11.00000 0.05 0.22 Q9 1 0.0492 0.8026 0.2123 11.00000 0.05 0.21 Q10 1 0.0793 0.6214 0.0971 11.00000 0.05 0.20 ; _database_code_depnum_ccdc_archive 'CCDC 943169' ####################################################################### # # 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_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 O5' _chemical_formula_sum 'C9 H14 O5' _chemical_formula_weight 202.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.8312(16) _cell_length_b 7.8846(9) _cell_length_c 17.820(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.3668(18) _cell_angle_gamma 90.00 _cell_volume 1922.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6096 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 30.34 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 21614 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 30.61 _reflns_number_total 5794 _reflns_number_gt 4526 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0582P)^2^+0.3180P] 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 5794 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.78360(8) 0.15212(13) 0.06730(6) 0.0198(2) Uani 1 1 d . . . O1 O 0.78773(6) 0.33098(10) 0.07137(5) 0.02358(18) Uani 1 1 d . . . C2 C 0.86371(9) 0.37191(15) 0.02681(7) 0.0258(2) Uani 1 1 d . . . H2 H 0.8611 0.4940 0.0114 0.031 Uiso 1 1 calc R . . C3 C 0.83624(10) 0.25598(16) -0.04107(7) 0.0305(3) Uani 1 1 d . . . H3A H 0.7881 0.3109 -0.0801 0.037 Uiso 1 1 calc R . . H3B H 0.8945 0.2237 -0.0641 0.037 Uiso 1 1 calc R . . O2 O 0.79433(6) 0.11039(10) -0.00866(4) 0.02597(19) Uani 1 1 d . . . C4 C 0.86895(8) 0.08135(14) 0.12346(6) 0.0205(2) Uani 1 1 d . . . H4 H 0.8657 0.1315 0.1746 0.025 Uiso 1 1 calc R . . C5 C 0.96463(8) 0.13952(15) 0.09696(7) 0.0269(2) Uani 1 1 d . . . H5A H 1.0195 0.1214 0.1384 0.032 Uiso 1 1 calc R . . H5B H 0.9769 0.0695 0.0532 0.032 Uiso 1 1 calc R . . C6 C 0.96134(9) 0.32736(16) 0.07385(8) 0.0291(3) Uani 1 1 d . . . H6A H 0.9715 0.3990 0.1199 0.035 Uiso 1 1 calc R . . H6B H 1.0148 0.3513 0.0440 0.035 Uiso 1 1 calc R . . O3 O 0.69701(6) 0.09228(10) 0.08588(5) 0.02595(18) Uani 1 1 d . . . C7 C 0.61118(9) 0.15069(17) 0.03639(9) 0.0358(3) Uani 1 1 d . . . H7A H 0.6115 0.2749 0.0342 0.054 Uiso 1 1 calc R . . H7B H 0.5524 0.1121 0.0561 0.054 Uiso 1 1 calc R . . H7C H 0.6115 0.1046 -0.0147 0.054 Uiso 1 1 calc R . . C8 C 0.86445(8) -0.11031(14) 0.12990(6) 0.0231(2) Uani 1 1 d . . . O4 O 0.89626(8) -0.20977(12) 0.08837(6) 0.0378(2) Uani 1 1 d . . . O5 O 0.82157(7) -0.15595(11) 0.18968(5) 0.0292(2) Uani 1 1 d . . . C9 C 0.81573(11) -0.33665(16) 0.20309(8) 0.0373(3) Uani 1 1 d . . . H9A H 0.7682 -0.3878 0.1634 0.056 Uiso 1 1 calc R . . H9B H 0.7950 -0.3561 0.2527 0.056 Uiso 1 1 calc R . . H9C H 0.8800 -0.3883 0.2023 0.056 Uiso 1 1 calc R . . C10 C 0.38126(8) 0.33539(13) 0.11736(6) 0.0180(2) Uani 1 1 d . . . O6 O 0.38686(6) 0.15615(9) 0.11641(4) 0.02083(17) Uani 1 1 d . . . C11 C 0.31448(8) 0.10644(14) 0.16304(6) 0.0221(2) Uani 1 1 d . . . H11 H 0.2958 -0.0155 0.1551 0.026 Uiso 1 1 calc R . . C12 C 0.23048(8) 0.22381(15) 0.13198(7) 0.0246(2) Uani 1 1 d . . . H12A H 0.1901 0.1736 0.0870 0.030 Uiso 1 1 calc R . . H12B H 0.1883 0.2488 0.1710 0.030 Uiso 1 1 calc R . . O7 O 0.28030(6) 0.37471(10) 0.11181(5) 0.02219(17) Uani 1 1 d . . . C13 C 0.43751(8) 0.39673(13) 0.19352(6) 0.0191(2) Uani 1 1 d . . . H13 H 0.5049 0.3476 0.1998 0.023 Uiso 1 1 calc R . . C14 C 0.38436(9) 0.32902(14) 0.25741(6) 0.0232(2) Uani 1 1 d . . . H14A H 0.4273 0.3421 0.3066 0.028 Uiso 1 1 calc R . . H14B H 0.3247 0.3972 0.2594 0.028 Uiso 1 1 calc R . . C15 C 0.35592(9) 0.14165(14) 0.24568(6) 0.0236(2) Uani 1 1 d . . . H15A H 0.4142 0.0697 0.2607 0.028 Uiso 1 1 calc R . . H15B H 0.3065 0.1119 0.2785 0.028 Uiso 1 1 calc R . . O8 O 0.42212(6) 0.40605(10) 0.05917(4) 0.02211(17) Uani 1 1 d . . . C16 C 0.37871(10) 0.35221(15) -0.01548(6) 0.0265(2) Uani 1 1 d . . . H16A H 0.3843 0.2288 -0.0195 0.040 Uiso 1 1 calc R . . H16B H 0.4127 0.4067 -0.0536 0.040 Uiso 1 1 calc R . . H16C H 0.3096 0.3846 -0.0241 0.040 Uiso 1 1 calc R . . C17 C 0.44545(8) 0.58889(14) 0.19520(6) 0.0206(2) Uani 1 1 d . . . O9 O 0.38107(7) 0.68497(11) 0.20600(6) 0.0321(2) Uani 1 1 d . . . O10 O 0.53466(6) 0.63992(10) 0.18368(5) 0.02326(17) Uani 1 1 d . . . C18 C 0.54883(10) 0.82152(15) 0.18379(7) 0.0291(3) Uani 1 1 d . . . H18A H 0.4995 0.8736 0.1457 0.044 Uiso 1 1 calc R . . H18B H 0.6142 0.8472 0.1718 0.044 Uiso 1 1 calc R . . H18C H 0.5424 0.8670 0.2340 0.044 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 0.0213(5) 0.0162(5) 0.0218(5) -0.0014(4) 0.0032(4) -0.0002(4) O1 0.0262(4) 0.0158(4) 0.0301(4) -0.0006(3) 0.0087(3) -0.0003(3) C2 0.0269(6) 0.0221(5) 0.0300(6) 0.0059(4) 0.0089(5) -0.0004(4) C3 0.0397(7) 0.0305(6) 0.0217(5) 0.0059(5) 0.0058(5) 0.0030(5) O2 0.0346(5) 0.0230(4) 0.0196(4) -0.0018(3) 0.0016(3) 0.0007(3) C4 0.0222(5) 0.0196(5) 0.0192(5) 0.0010(4) 0.0019(4) -0.0013(4) C5 0.0202(5) 0.0285(6) 0.0313(6) 0.0075(5) 0.0017(4) -0.0005(4) C6 0.0258(6) 0.0274(6) 0.0346(6) 0.0052(5) 0.0057(5) -0.0054(5) O3 0.0202(4) 0.0218(4) 0.0356(5) 0.0043(3) 0.0031(3) -0.0008(3) C7 0.0203(6) 0.0292(6) 0.0562(9) 0.0079(6) -0.0008(5) 0.0020(5) C8 0.0215(5) 0.0228(5) 0.0245(5) 0.0039(4) 0.0009(4) 0.0009(4) O4 0.0468(6) 0.0251(4) 0.0452(6) -0.0007(4) 0.0188(5) 0.0047(4) O5 0.0371(5) 0.0222(4) 0.0292(4) 0.0070(3) 0.0077(4) -0.0003(3) C9 0.0478(8) 0.0235(6) 0.0407(7) 0.0121(5) 0.0072(6) -0.0011(5) C10 0.0192(5) 0.0158(5) 0.0197(5) -0.0002(4) 0.0046(4) 0.0009(4) O6 0.0243(4) 0.0155(4) 0.0238(4) -0.0008(3) 0.0071(3) -0.0001(3) C11 0.0237(5) 0.0188(5) 0.0246(5) -0.0003(4) 0.0064(4) -0.0037(4) C12 0.0207(5) 0.0264(6) 0.0270(6) -0.0006(4) 0.0047(4) -0.0040(4) O7 0.0191(4) 0.0218(4) 0.0259(4) 0.0018(3) 0.0038(3) 0.0012(3) C13 0.0211(5) 0.0169(5) 0.0192(5) -0.0004(4) 0.0023(4) -0.0006(4) C14 0.0295(6) 0.0222(5) 0.0183(5) 0.0002(4) 0.0045(4) -0.0036(4) C15 0.0282(6) 0.0205(5) 0.0226(5) 0.0032(4) 0.0053(4) -0.0020(4) O8 0.0276(4) 0.0215(4) 0.0182(4) 0.0001(3) 0.0065(3) -0.0036(3) C16 0.0359(6) 0.0264(6) 0.0176(5) -0.0006(4) 0.0051(4) 0.0005(5) C17 0.0247(5) 0.0200(5) 0.0176(5) -0.0014(4) 0.0046(4) -0.0027(4) O9 0.0329(5) 0.0208(4) 0.0461(5) -0.0036(4) 0.0168(4) 0.0011(3) O10 0.0246(4) 0.0185(4) 0.0272(4) -0.0013(3) 0.0054(3) -0.0040(3) C18 0.0348(6) 0.0189(5) 0.0349(6) -0.0025(5) 0.0087(5) -0.0069(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 O3 1.3719(13) . ? C1 O1 1.4128(12) . ? C1 O2 1.4215(13) . ? C1 C4 1.5370(15) . ? O1 C2 1.4430(14) . ? C2 C3 1.5197(18) . ? C2 C6 1.5231(17) . ? C3 O2 1.4439(15) . ? C4 C8 1.5175(15) . ? C4 C5 1.5384(16) . ? C5 C6 1.5361(16) . ? O3 C7 1.4472(15) . ? C8 O4 1.2046(14) . ? C8 O5 1.3416(14) . ? O5 C9 1.4488(15) . ? C10 O8 1.3695(12) . ? C10 O6 1.4156(12) . ? C10 O7 1.4197(13) . ? C10 C13 1.5408(15) . ? O6 C11 1.4452(13) . ? C11 C12 1.5250(16) . ? C11 C15 1.5260(16) . ? C12 O7 1.4463(14) . ? C13 C17 1.5191(15) . ? C13 C14 1.5380(15) . ? C14 C15 1.5353(15) . ? O8 C16 1.4415(14) . ? C17 O9 1.2058(14) . ? C17 O10 1.3417(13) . ? O10 C18 1.4452(13) . ? 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 O3 C1 O1 111.16(9) . . ? O3 C1 O2 111.47(9) . . ? O1 C1 O2 105.72(8) . . ? O3 C1 C4 109.44(9) . . ? O1 C1 C4 107.90(9) . . ? O2 C1 C4 111.05(9) . . ? C1 O1 C2 102.84(8) . . ? O1 C2 C3 100.71(9) . . ? O1 C2 C6 107.69(9) . . ? C3 C2 C6 113.47(10) . . ? O2 C3 C2 103.19(9) . . ? C1 O2 C3 107.49(8) . . ? C8 C4 C1 112.01(9) . . ? C8 C4 C5 111.51(9) . . ? C1 C4 C5 107.78(9) . . ? C6 C5 C4 112.11(10) . . ? C2 C6 C5 111.05(10) . . ? C1 O3 C7 114.27(9) . . ? O4 C8 O5 123.81(11) . . ? O4 C8 C4 125.39(11) . . ? O5 C8 C4 110.79(10) . . ? C8 O5 C9 115.88(10) . . ? O8 C10 O6 111.58(8) . . ? O8 C10 O7 111.62(8) . . ? O6 C10 O7 105.80(8) . . ? O8 C10 C13 109.15(8) . . ? O6 C10 C13 107.60(8) . . ? O7 C10 C13 111.00(8) . . ? C10 O6 C11 102.72(8) . . ? O6 C11 C12 100.46(8) . . ? O6 C11 C15 108.13(9) . . ? C12 C11 C15 113.53(9) . . ? O7 C12 C11 102.95(8) . . ? C10 O7 C12 107.60(8) . . ? C17 C13 C14 111.88(9) . . ? C17 C13 C10 110.87(9) . . ? C14 C13 C10 107.97(9) . . ? C15 C14 C13 111.95(9) . . ? C11 C15 C14 111.05(9) . . ? C10 O8 C16 114.62(8) . . ? O9 C17 O10 123.58(10) . . ? O9 C17 C13 125.23(10) . . ? O10 C17 C13 111.19(9) . . ? C17 O10 C18 115.11(9) . . ? 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 O3 C1 O1 C2 -161.23(9) . . . . ? O2 C1 O1 C2 -40.12(10) . . . . ? C4 C1 O1 C2 78.77(10) . . . . ? C1 O1 C2 C3 44.26(10) . . . . ? C1 O1 C2 C6 -74.81(11) . . . . ? O1 C2 C3 O2 -32.45(11) . . . . ? C6 C2 C3 O2 82.34(12) . . . . ? O3 C1 O2 C3 139.54(9) . . . . ? O1 C1 O2 C3 18.63(11) . . . . ? C4 C1 O2 C3 -98.15(10) . . . . ? C2 C3 O2 C1 9.05(12) . . . . ? O3 C1 C4 C8 52.50(12) . . . . ? O1 C1 C4 C8 173.58(9) . . . . ? O2 C1 C4 C8 -70.98(11) . . . . ? O3 C1 C4 C5 175.53(9) . . . . ? O1 C1 C4 C5 -63.39(11) . . . . ? O2 C1 C4 C5 52.04(12) . . . . ? C8 C4 C5 C6 167.80(10) . . . . ? C1 C4 C5 C6 44.47(13) . . . . ? O1 C2 C6 C5 57.57(13) . . . . ? C3 C2 C6 C5 -52.99(13) . . . . ? C4 C5 C6 C2 -43.14(14) . . . . ? O1 C1 O3 C7 61.07(13) . . . . ? O2 C1 O3 C7 -56.60(12) . . . . ? C4 C1 O3 C7 -179.84(10) . . . . ? C1 C4 C8 O4 84.98(14) . . . . ? C5 C4 C8 O4 -35.91(16) . . . . ? C1 C4 C8 O5 -96.29(11) . . . . ? C5 C4 C8 O5 142.82(10) . . . . ? O4 C8 O5 C9 0.57(17) . . . . ? C4 C8 O5 C9 -178.18(10) . . . . ? O8 C10 O6 C11 -161.75(8) . . . . ? O7 C10 O6 C11 -40.17(10) . . . . ? C13 C10 O6 C11 78.55(9) . . . . ? C10 O6 C11 C12 44.72(10) . . . . ? C10 O6 C11 C15 -74.47(10) . . . . ? O6 C11 C12 O7 -33.23(10) . . . . ? C15 C11 C12 O7 81.96(11) . . . . ? O8 C10 O7 C12 139.66(9) . . . . ? O6 C10 O7 C12 18.11(11) . . . . ? C13 C10 O7 C12 -98.33(10) . . . . ? C11 C12 O7 C10 9.86(11) . . . . ? O8 C10 C13 C17 51.93(11) . . . . ? O6 C10 C13 C17 173.16(8) . . . . ? O7 C10 C13 C17 -71.52(11) . . . . ? O8 C10 C13 C14 174.81(8) . . . . ? O6 C10 C13 C14 -63.95(10) . . . . ? O7 C10 C13 C14 51.37(11) . . . . ? C17 C13 C14 C15 167.26(9) . . . . ? C10 C13 C14 C15 45.00(12) . . . . ? O6 C11 C15 C14 57.26(12) . . . . ? C12 C11 C15 C14 -53.29(13) . . . . ? C13 C14 C15 C11 -43.04(13) . . . . ? O6 C10 O8 C16 58.48(12) . . . . ? O7 C10 O8 C16 -59.66(11) . . . . ? C13 C10 O8 C16 177.27(9) . . . . ? C14 C13 C17 O9 -42.51(15) . . . . ? C10 C13 C17 O9 78.08(14) . . . . ? C14 C13 C17 O10 136.92(9) . . . . ? C10 C13 C17 O10 -102.48(10) . . . . ? O9 C17 O10 C18 -0.97(16) . . . . ? C13 C17 O10 C18 179.59(9) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.404 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.048 _iucr_refine_instruction_details ; TITL 1b in P2(1)/n CELL 0.71073 13.8312 7.8846 17.820 90.000 98.3668 90.000 ZERR 8.00 0.0016 0.0009 0.002 0.000 0.0018 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O UNIT 72 112 40 TEMP -123 SIZE 0.20 0.30 0.75 ACTA CONF WPDB -1 OMIT 0 4 2 L.S. 6 BOND FMAP 2 PLAN 10 REM EXTI 0.000000 INSIG. WGHT 0.058200 0.318000 FVAR 0.13400 C1 1 0.783601 0.152117 0.067297 11.00000 0.02134 0.01623 = 0.02183 -0.00135 0.00316 -0.00023 O1 3 0.787729 0.330976 0.071374 11.00000 0.02624 0.01579 = 0.03010 -0.00056 0.00873 -0.00027 C2 1 0.863713 0.371906 0.026811 11.00000 0.02686 0.02209 = 0.03001 0.00586 0.00892 -0.00035 AFIX 13 H2 2 0.861133 0.493991 0.011444 11.00000 -1.20000 AFIX 0 C3 1 0.836242 0.255978 -0.041074 11.00000 0.03969 0.03048 = 0.02167 0.00592 0.00585 0.00296 AFIX 23 H3A 2 0.788062 0.310930 -0.080077 11.00000 -1.20000 H3B 2 0.894544 0.223719 -0.064126 11.00000 -1.20000 AFIX 0 O2 3 0.794331 0.110386 -0.008657 11.00000 0.03456 0.02302 = 0.01963 -0.00183 0.00156 0.00071 C4 1 0.868949 0.081351 0.123455 11.00000 0.02220 0.01964 = 0.01920 0.00097 0.00193 -0.00134 AFIX 13 H4 2 0.865651 0.131494 0.174565 11.00000 -1.20000 AFIX 0 C5 1 0.964634 0.139522 0.096958 11.00000 0.02019 0.02848 = 0.03134 0.00749 0.00166 -0.00047 AFIX 23 H5A 2 1.019543 0.121438 0.138438 11.00000 -1.20000 H5B 2 0.976868 0.069462 0.053204 11.00000 -1.20000 AFIX 0 C6 1 0.961340 0.327357 0.073849 11.00000 0.02581 0.02738 = 0.03462 0.00517 0.00566 -0.00540 AFIX 23 H6A 2 0.971509 0.399002 0.119948 11.00000 -1.20000 H6B 2 1.014840 0.351320 0.044027 11.00000 -1.20000 AFIX 0 O3 3 0.697010 0.092285 0.085881 11.00000 0.02017 0.02185 = 0.03557 0.00435 0.00315 -0.00082 C7 1 0.611180 0.150690 0.036388 11.00000 0.02026 0.02922 = 0.05615 0.00786 -0.00080 0.00204 AFIX 137 H7A 2 0.611538 0.274883 0.034246 11.00000 -1.50000 H7B 2 0.552355 0.112099 0.056057 11.00000 -1.50000 H7C 2 0.611527 0.104636 -0.014652 11.00000 -1.50000 AFIX 0 C8 1 0.864452 -0.110310 0.129900 11.00000 0.02150 0.02275 = 0.02447 0.00385 0.00093 0.00092 O4 3 0.896264 -0.209774 0.088370 11.00000 0.04676 0.02507 = 0.04521 -0.00073 0.01877 0.00469 O5 3 0.821572 -0.155954 0.189681 11.00000 0.03708 0.02220 = 0.02920 0.00703 0.00770 -0.00028 C9 1 0.815732 -0.336648 0.203087 11.00000 0.04782 0.02355 = 0.04074 0.01212 0.00723 -0.00109 AFIX 137 H9A 2 0.768184 -0.387804 0.163381 11.00000 -1.50000 H9B 2 0.795034 -0.356113 0.252688 11.00000 -1.50000 H9C 2 0.880027 -0.388255 0.202260 11.00000 -1.50000 AFIX 0 C10 1 0.381258 0.335388 0.117360 11.00000 0.01916 0.01579 = 0.01970 -0.00025 0.00465 0.00088 O6 3 0.386862 0.156148 0.116411 11.00000 0.02429 0.01548 = 0.02382 -0.00077 0.00713 -0.00011 C11 1 0.314477 0.106435 0.163042 11.00000 0.02366 0.01878 = 0.02459 -0.00031 0.00644 -0.00366 AFIX 13 H11 2 0.295845 -0.015484 0.155072 11.00000 -1.20000 AFIX 0 C12 1 0.230477 0.223808 0.131975 11.00000 0.02073 0.02644 = 0.02696 -0.00056 0.00472 -0.00403 AFIX 23 H12A 2 0.190098 0.173573 0.087030 11.00000 -1.20000 H12B 2 0.188332 0.248811 0.170995 11.00000 -1.20000 AFIX 0 O7 3 0.280299 0.374714 0.111809 11.00000 0.01908 0.02175 = 0.02589 0.00180 0.00379 0.00116 C13 1 0.437512 0.396735 0.193520 11.00000 0.02114 0.01687 = 0.01918 -0.00037 0.00232 -0.00061 AFIX 13 H13 2 0.504873 0.347645 0.199829 11.00000 -1.20000 AFIX 0 C14 1 0.384356 0.329020 0.257407 11.00000 0.02950 0.02216 = 0.01828 0.00022 0.00446 -0.00363 AFIX 23 H14A 2 0.427318 0.342051 0.306585 11.00000 -1.20000 H14B 2 0.324690 0.397215 0.259431 11.00000 -1.20000 AFIX 0 C15 1 0.355923 0.141647 0.245679 11.00000 0.02817 0.02052 = 0.02260 0.00318 0.00525 -0.00204 AFIX 23 H15A 2 0.414188 0.069672 0.260654 11.00000 -1.20000 H15B 2 0.306539 0.111905 0.278510 11.00000 -1.20000 AFIX 0 O8 3 0.422123 0.406048 0.059173 11.00000 0.02764 0.02147 = 0.01818 0.00008 0.00652 -0.00361 C16 1 0.378709 0.352211 -0.015477 11.00000 0.03587 0.02637 = 0.01761 -0.00063 0.00514 0.00049 AFIX 137 H16A 2 0.384336 0.228753 -0.019512 11.00000 -1.50000 H16B 2 0.412705 0.406699 -0.053610 11.00000 -1.50000 H16C 2 0.309571 0.384580 -0.024061 11.00000 -1.50000 AFIX 0 C17 1 0.445452 0.588894 0.195198 11.00000 0.02474 0.02002 = 0.01756 -0.00137 0.00456 -0.00267 O9 3 0.381068 0.684972 0.206002 11.00000 0.03287 0.02076 = 0.04609 -0.00364 0.01679 0.00110 O10 3 0.534662 0.639916 0.183678 11.00000 0.02461 0.01847 = 0.02720 -0.00132 0.00539 -0.00397 C18 1 0.548828 0.821520 0.183794 11.00000 0.03480 0.01888 = 0.03485 -0.00245 0.00874 -0.00688 AFIX 137 H18A 2 0.499491 0.873570 0.145684 11.00000 -1.50000 H18B 2 0.614181 0.847170 0.171758 11.00000 -1.50000 H18C 2 0.542417 0.866969 0.234019 11.00000 -1.50000 HKLF 4 REM 1b in P2(1)/n REM R1 = 0.0418 for 4526 Fo > 4sig(Fo) and 0.0564 for all 5794 data REM 257 parameters refined using 0 restraints END WGHT 0.0581 0.3196 REM Highest difference peak 0.404, deepest hole -0.214, 1-sigma level 0.048 Q1 1 0.4421 0.4954 0.1945 11.00000 0.05 0.40 Q2 1 0.3334 0.1328 0.2042 11.00000 0.05 0.38 Q3 1 0.8627 -0.0085 0.1252 11.00000 0.05 0.37 Q4 1 0.8275 0.1093 0.0976 11.00000 0.05 0.31 Q5 1 0.9127 0.3443 0.0449 11.00000 0.05 0.30 Q6 1 0.4121 0.3678 0.1566 11.00000 0.05 0.30 Q7 1 0.3759 0.2322 0.2483 11.00000 0.05 0.29 Q8 1 0.9580 0.2385 0.0906 11.00000 0.05 0.29 Q9 1 0.9134 0.1188 0.1095 11.00000 0.05 0.29 Q10 1 0.2675 0.1606 0.1529 11.00000 0.05 0.28 ; _database_code_depnum_ccdc_archive 'CCDC 943170' ####################################################################### # # 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_15b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 O5' _chemical_formula_sum 'C18 H24 O5' _chemical_formula_weight 320.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.2706(9) _cell_length_b 7.5565(5) _cell_length_c 17.6919(13) _cell_angle_alpha 90.00 _cell_angle_beta 109.8974(10) _cell_angle_gamma 90.00 _cell_volume 1668.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6260 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.13 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 1.06 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15033 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.16 _reflns_number_total 3697 _reflns_number_gt 3177 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0440P)^2^+0.5093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3697 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.29598(8) 0.41782(14) 0.13466(6) 0.0187(2) Uani 1 1 d . . . O1 O 0.29019(6) 0.55683(10) 0.07922(4) 0.02029(18) Uani 1 1 d . . . C2 C 0.29736(9) 0.72390(15) 0.12125(7) 0.0217(2) Uani 1 1 d . . . H2 H 0.3576 0.7960 0.1156 0.026 Uiso 1 1 calc R . . C3 C 0.32504(9) 0.66377(15) 0.20891(7) 0.0221(2) Uani 1 1 d . . . H3 H 0.2966 0.7483 0.2402 0.026 Uiso 1 1 calc R . . O2 O 0.27018(6) 0.49603(10) 0.19821(4) 0.02098(18) Uani 1 1 d . . . C4 C 0.44338(9) 0.62656(16) 0.25155(7) 0.0232(2) Uani 1 1 d . . . H4A H 0.4536 0.5690 0.3039 0.028 Uiso 1 1 calc R . . H4B H 0.4837 0.7394 0.2619 0.028 Uiso 1 1 calc R . . C5 C 0.48660(8) 0.50549(15) 0.19988(7) 0.0203(2) Uani 1 1 d . . . H5A H 0.5588 0.4628 0.2327 0.024 Uiso 1 1 calc R . . H5B H 0.4938 0.5746 0.1545 0.024 Uiso 1 1 calc R . . C6 C 0.41278(8) 0.34444(14) 0.16643(6) 0.0183(2) Uani 1 1 d . . . O3 O 0.22483(6) 0.28496(10) 0.10028(5) 0.02247(18) Uani 1 1 d . . . C7 C 0.11454(9) 0.33940(17) 0.06843(8) 0.0291(3) Uani 1 1 d . . . H7A H 0.0928 0.3885 0.1118 0.044 Uiso 1 1 calc R . . H7B H 0.0695 0.2371 0.0448 0.044 Uiso 1 1 calc R . . H7C H 0.1062 0.4297 0.0270 0.044 Uiso 1 1 calc R . . C8 C 0.19299(10) 0.82525(16) 0.08711(7) 0.0268(3) Uani 1 1 d . . . H8A H 0.1988 0.9381 0.1167 0.032 Uiso 1 1 calc R . . H8B H 0.1345 0.7553 0.0953 0.032 Uiso 1 1 calc R . . C9 C 0.16479(10) 0.86472(18) -0.00212(8) 0.0333(3) Uani 1 1 d . . . H9A H 0.2216 0.9366 -0.0104 0.050 Uiso 1 1 calc R . . H9B H 0.0969 0.9296 -0.0215 0.050 Uiso 1 1 calc R . . H9C H 0.1577 0.7533 -0.0319 0.050 Uiso 1 1 calc R . . C10 C 0.42356(9) 0.20149(15) 0.23164(7) 0.0216(2) Uani 1 1 d . . . H10A H 0.3945 0.2492 0.2721 0.026 Uiso 1 1 calc R . . H10B H 0.3798 0.0974 0.2063 0.026 Uiso 1 1 calc R . . C11 C 0.53813(9) 0.14228(15) 0.27379(7) 0.0239(2) Uani 1 1 d . . . C12 C 0.59553(10) 0.2063(2) 0.35006(7) 0.0337(3) Uani 1 1 d . . . H12 H 0.5612 0.2839 0.3759 0.040 Uiso 1 1 calc R . . C13 C 0.70181(11) 0.1596(2) 0.38927(9) 0.0431(4) Uani 1 1 d . . . H13 H 0.7395 0.2052 0.4413 0.052 Uiso 1 1 calc R . . C14 C 0.75244(11) 0.0466(2) 0.35227(9) 0.0435(4) Uani 1 1 d . . . H14 H 0.8253 0.0150 0.3786 0.052 Uiso 1 1 calc R . . C15 C 0.69683(11) -0.0202(2) 0.27696(9) 0.0399(3) Uani 1 1 d . . . H15 H 0.7314 -0.0989 0.2518 0.048 Uiso 1 1 calc R . . C16 C 0.59040(10) 0.02696(17) 0.23769(8) 0.0305(3) Uani 1 1 d . . . H16 H 0.5530 -0.0197 0.1858 0.037 Uiso 1 1 calc R . . C17 C 0.43602(8) 0.25278(15) 0.09671(6) 0.0195(2) Uani 1 1 d . . . O4 O 0.39954(7) 0.11175(11) 0.06939(5) 0.0291(2) Uani 1 1 d . . . O5 O 0.50390(7) 0.34258(11) 0.07000(5) 0.0275(2) Uani 1 1 d . . . C18 C 0.53490(12) 0.25230(18) 0.00890(8) 0.0352(3) Uani 1 1 d . . . H18A H 0.5702 0.1403 0.0306 0.053 Uiso 1 1 calc R . . H18B H 0.5844 0.3272 -0.0072 0.053 Uiso 1 1 calc R . . H18C H 0.4710 0.2284 -0.0380 0.053 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 0.0189(5) 0.0189(5) 0.0211(5) -0.0006(4) 0.0103(4) -0.0014(4) O1 0.0243(4) 0.0181(4) 0.0213(4) -0.0001(3) 0.0114(3) -0.0001(3) C2 0.0244(6) 0.0181(5) 0.0261(6) -0.0020(4) 0.0130(5) -0.0015(4) C3 0.0253(6) 0.0195(5) 0.0257(6) -0.0035(4) 0.0142(5) -0.0010(4) O2 0.0223(4) 0.0215(4) 0.0242(4) -0.0010(3) 0.0145(3) -0.0008(3) C4 0.0249(6) 0.0245(6) 0.0220(5) -0.0046(4) 0.0104(4) -0.0034(4) C5 0.0182(5) 0.0225(5) 0.0222(5) -0.0025(4) 0.0093(4) -0.0029(4) C6 0.0168(5) 0.0201(5) 0.0203(5) -0.0008(4) 0.0091(4) -0.0012(4) O3 0.0165(4) 0.0214(4) 0.0296(4) -0.0014(3) 0.0080(3) -0.0024(3) C7 0.0166(5) 0.0328(7) 0.0361(7) -0.0008(5) 0.0067(5) -0.0020(5) C8 0.0263(6) 0.0215(6) 0.0348(6) 0.0010(5) 0.0134(5) 0.0021(5) C9 0.0281(6) 0.0319(7) 0.0376(7) 0.0081(6) 0.0083(5) 0.0002(5) C10 0.0203(5) 0.0237(6) 0.0239(5) 0.0025(4) 0.0114(4) 0.0003(4) C11 0.0211(5) 0.0256(6) 0.0273(6) 0.0065(5) 0.0112(5) 0.0012(4) C12 0.0301(6) 0.0451(8) 0.0263(6) 0.0048(6) 0.0101(5) 0.0067(6) C13 0.0320(7) 0.0615(10) 0.0301(7) 0.0080(7) 0.0033(6) 0.0035(7) C14 0.0240(6) 0.0572(9) 0.0469(8) 0.0177(7) 0.0088(6) 0.0105(6) C15 0.0305(7) 0.0398(8) 0.0545(9) 0.0078(7) 0.0211(6) 0.0111(6) C16 0.0285(6) 0.0276(6) 0.0370(7) 0.0022(5) 0.0132(5) 0.0033(5) C17 0.0177(5) 0.0207(5) 0.0218(5) 0.0007(4) 0.0088(4) 0.0013(4) O4 0.0316(4) 0.0257(4) 0.0356(5) -0.0101(4) 0.0186(4) -0.0073(4) O5 0.0348(5) 0.0249(4) 0.0341(5) -0.0062(3) 0.0262(4) -0.0054(3) C18 0.0478(8) 0.0316(7) 0.0413(7) -0.0073(6) 0.0346(7) -0.0041(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.3706(13) . ? C1 O2 1.4116(13) . ? C1 O1 1.4213(13) . ? C1 C6 1.5598(14) . ? O1 C2 1.4518(13) . ? C2 C8 1.5166(16) . ? C2 C3 1.5359(16) . ? C3 O2 1.4418(13) . ? C3 C4 1.5193(16) . ? C4 C5 1.5356(15) . ? C5 C6 1.5480(15) . ? C6 C17 1.5345(14) . ? C6 C10 1.5512(15) . ? O3 C7 1.4379(13) . ? C8 C9 1.5229(18) . ? C10 C11 1.5153(15) . ? C11 C12 1.3913(18) . ? C11 C16 1.3964(17) . ? C12 C13 1.3888(19) . ? C13 C14 1.382(2) . ? C14 C15 1.380(2) . ? C15 C16 1.3916(18) . ? C17 O4 1.2018(14) . ? C17 O5 1.3361(13) . ? O5 C18 1.4512(14) . ? 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 O3 C1 O2 110.06(8) . . ? O3 C1 O1 111.58(9) . . ? O2 C1 O1 105.63(8) . . ? O3 C1 C6 110.46(9) . . ? O2 C1 C6 110.03(8) . . ? O1 C1 C6 108.97(8) . . ? C1 O1 C2 108.09(8) . . ? O1 C2 C8 110.08(9) . . ? O1 C2 C3 102.20(8) . . ? C8 C2 C3 115.06(9) . . ? O2 C3 C4 107.03(9) . . ? O2 C3 C2 101.01(8) . . ? C4 C3 C2 114.06(9) . . ? C1 O2 C3 102.95(8) . . ? C3 C4 C5 110.31(9) . . ? C4 C5 C6 112.33(9) . . ? C17 C6 C5 112.83(8) . . ? C17 C6 C10 106.90(9) . . ? C5 C6 C10 112.14(9) . . ? C17 C6 C1 108.53(8) . . ? C5 C6 C1 106.27(8) . . ? C10 C6 C1 110.14(8) . . ? C1 O3 C7 114.83(9) . . ? C2 C8 C9 112.37(10) . . ? C11 C10 C6 113.25(9) . . ? C12 C11 C16 117.86(11) . . ? C12 C11 C10 120.07(11) . . ? C16 C11 C10 122.05(11) . . ? C13 C12 C11 121.59(13) . . ? C14 C13 C12 119.69(13) . . ? C15 C14 C13 119.80(13) . . ? C14 C15 C16 120.44(13) . . ? C15 C16 C11 120.61(13) . . ? O4 C17 O5 122.40(10) . . ? O4 C17 C6 124.05(10) . . ? O5 C17 C6 113.53(9) . . ? C17 O5 C18 114.89(9) . . ? 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 O3 C1 O1 C2 138.82(9) . . . . ? O2 C1 O1 C2 19.23(10) . . . . ? C6 C1 O1 C2 -98.95(9) . . . . ? C1 O1 C2 C8 -114.41(9) . . . . ? C1 O1 C2 C3 8.31(10) . . . . ? O1 C2 C3 O2 -31.92(10) . . . . ? C8 C2 C3 O2 87.35(10) . . . . ? O1 C2 C3 C4 82.51(11) . . . . ? C8 C2 C3 C4 -158.22(10) . . . . ? O3 C1 O2 C3 -161.12(8) . . . . ? O1 C1 O2 C3 -40.53(10) . . . . ? C6 C1 O2 C3 76.93(10) . . . . ? C4 C3 O2 C1 -75.22(10) . . . . ? C2 C3 O2 C1 44.37(10) . . . . ? O2 C3 C4 C5 61.39(11) . . . . ? C2 C3 C4 C5 -49.43(12) . . . . ? C3 C4 C5 C6 -47.24(12) . . . . ? C4 C5 C6 C17 163.58(9) . . . . ? C4 C5 C6 C10 -75.63(11) . . . . ? C4 C5 C6 C1 44.76(11) . . . . ? O3 C1 C6 C17 55.60(11) . . . . ? O2 C1 C6 C17 177.31(8) . . . . ? O1 C1 C6 C17 -67.31(10) . . . . ? O3 C1 C6 C5 177.21(8) . . . . ? O2 C1 C6 C5 -61.08(10) . . . . ? O1 C1 C6 C5 54.30(10) . . . . ? O3 C1 C6 C10 -61.10(11) . . . . ? O2 C1 C6 C10 60.61(11) . . . . ? O1 C1 C6 C10 175.99(8) . . . . ? O2 C1 O3 C7 58.77(12) . . . . ? O1 C1 O3 C7 -58.16(12) . . . . ? C6 C1 O3 C7 -179.54(9) . . . . ? O1 C2 C8 C9 -59.45(12) . . . . ? C3 C2 C8 C9 -174.25(10) . . . . ? C17 C6 C10 C11 70.40(11) . . . . ? C5 C6 C10 C11 -53.75(12) . . . . ? C1 C6 C10 C11 -171.88(9) . . . . ? C6 C10 C11 C12 101.82(12) . . . . ? C6 C10 C11 C16 -76.59(14) . . . . ? C16 C11 C12 C13 0.72(19) . . . . ? C10 C11 C12 C13 -177.75(12) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 -0.60(18) . . . . ? C10 C11 C16 C15 177.83(11) . . . . ? C5 C6 C17 O4 168.95(10) . . . . ? C10 C6 C17 O4 45.21(14) . . . . ? C1 C6 C17 O4 -73.56(13) . . . . ? C5 C6 C17 O5 -9.25(13) . . . . ? C10 C6 C17 O5 -132.99(10) . . . . ? C1 C6 C17 O5 108.25(10) . . . . ? O4 C17 O5 C18 -3.39(16) . . . . ? C6 C17 O5 C18 174.84(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.038 _iucr_refine_instruction_details ; TITL 15b in P2(1)/n CELL 0.71073 13.2706 7.5565 17.6919 90.000 109.8974 90.000 ZERR 4.00 0.0009 0.0005 0.0013 0.000 0.0010 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O UNIT 72 96 20 TEMP -123 SIZE 0.10 0.33 1.06 ACTA CONF WPDB -1 L.S. 6 BOND FMAP 2 PLAN 10 REM EXTI 0.000000 insig. WGHT 0.044000 0.509300 FVAR 0.19224 C1 1 0.295977 0.417821 0.134661 11.00000 0.01889 0.01891 = 0.02107 -0.00059 0.01032 -0.00145 O1 3 0.290190 0.556833 0.079221 11.00000 0.02425 0.01815 = 0.02130 -0.00013 0.01144 -0.00012 C2 1 0.297360 0.723902 0.121249 11.00000 0.02443 0.01807 = 0.02610 -0.00201 0.01297 -0.00145 AFIX 13 H2 2 0.357585 0.795990 0.115588 11.00000 -1.20000 AFIX 0 C3 1 0.325036 0.663771 0.208910 11.00000 0.02529 0.01949 = 0.02574 -0.00352 0.01424 -0.00096 AFIX 13 H3 2 0.296553 0.748270 0.240222 11.00000 -1.20000 AFIX 0 O2 3 0.270178 0.496029 0.198213 11.00000 0.02232 0.02146 = 0.02422 -0.00098 0.01450 -0.00080 C4 1 0.443383 0.626556 0.251545 11.00000 0.02493 0.02448 = 0.02195 -0.00463 0.01039 -0.00344 AFIX 23 H4A 2 0.453620 0.569023 0.303911 11.00000 -1.20000 H4B 2 0.483742 0.739351 0.261932 11.00000 -1.20000 AFIX 0 C5 1 0.486599 0.505492 0.199878 11.00000 0.01823 0.02246 = 0.02217 -0.00252 0.00933 -0.00294 AFIX 23 H5A 2 0.558765 0.462763 0.232703 11.00000 -1.20000 H5B 2 0.493813 0.574605 0.154455 11.00000 -1.20000 AFIX 0 C6 1 0.412782 0.344438 0.166425 11.00000 0.01681 0.02011 = 0.02025 -0.00077 0.00910 -0.00124 O3 3 0.224830 0.284959 0.100282 11.00000 0.01652 0.02139 = 0.02963 -0.00139 0.00801 -0.00241 C7 1 0.114538 0.339403 0.068425 11.00000 0.01662 0.03281 = 0.03613 -0.00081 0.00668 -0.00198 AFIX 137 H7A 2 0.092778 0.388517 0.111786 11.00000 -1.50000 H7B 2 0.069478 0.237054 0.044788 11.00000 -1.50000 H7C 2 0.106192 0.429745 0.026991 11.00000 -1.50000 AFIX 0 C8 1 0.192993 0.825252 0.087113 11.00000 0.02632 0.02147 = 0.03484 0.00096 0.01342 0.00213 AFIX 23 H8A 2 0.198837 0.938080 0.116747 11.00000 -1.20000 H8B 2 0.134466 0.755276 0.095278 11.00000 -1.20000 AFIX 0 C9 1 0.164794 0.864718 -0.002121 11.00000 0.02813 0.03188 = 0.03759 0.00810 0.00828 0.00020 AFIX 137 H9A 2 0.221634 0.936570 -0.010399 11.00000 -1.50000 H9B 2 0.096868 0.929635 -0.021522 11.00000 -1.50000 H9C 2 0.157733 0.753345 -0.031865 11.00000 -1.50000 AFIX 0 C10 1 0.423557 0.201492 0.231642 11.00000 0.02034 0.02368 = 0.02387 0.00255 0.01144 0.00034 AFIX 23 H10A 2 0.394490 0.249246 0.272127 11.00000 -1.20000 H10B 2 0.379775 0.097425 0.206253 11.00000 -1.20000 AFIX 0 C11 1 0.538127 0.142280 0.273790 11.00000 0.02113 0.02565 = 0.02730 0.00653 0.01125 0.00125 C12 1 0.595532 0.206321 0.350060 11.00000 0.03012 0.04506 = 0.02627 0.00484 0.01010 0.00674 AFIX 43 H12 2 0.561205 0.283859 0.375944 11.00000 -1.20000 AFIX 0 C13 1 0.701810 0.159632 0.389272 11.00000 0.03204 0.06155 = 0.03012 0.00796 0.00330 0.00349 AFIX 43 H13 2 0.739514 0.205194 0.441294 11.00000 -1.20000 AFIX 0 C14 1 0.752441 0.046624 0.352272 11.00000 0.02396 0.05719 = 0.04692 0.01767 0.00885 0.01048 AFIX 43 H14 2 0.825309 0.014990 0.378578 11.00000 -1.20000 AFIX 0 C15 1 0.696826 -0.020189 0.276959 11.00000 0.03051 0.03980 = 0.05445 0.00783 0.02114 0.01110 AFIX 43 H15 2 0.731438 -0.098878 0.251769 11.00000 -1.20000 AFIX 0 C16 1 0.590397 0.026961 0.237693 11.00000 0.02853 0.02763 = 0.03697 0.00223 0.01324 0.00334 AFIX 43 H16 2 0.552954 -0.019738 0.185848 11.00000 -1.20000 AFIX 0 C17 1 0.436016 0.252782 0.096714 11.00000 0.01766 0.02075 = 0.02178 0.00074 0.00878 0.00127 O4 3 0.399539 0.111753 0.069395 11.00000 0.03163 0.02573 = 0.03555 -0.01014 0.01864 -0.00730 O5 3 0.503904 0.342581 0.070002 11.00000 0.03481 0.02486 = 0.03410 -0.00620 0.02620 -0.00536 C18 1 0.534902 0.252300 0.008897 11.00000 0.04781 0.03156 = 0.04132 -0.00731 0.03462 -0.00412 AFIX 137 H18A 2 0.570232 0.140336 0.030584 11.00000 -1.50000 H18B 2 0.584420 0.327158 -0.007205 11.00000 -1.50000 H18C 2 0.470985 0.228439 -0.037951 11.00000 -1.50000 HKLF 4 REM 15b in P2(1)/n REM R1 = 0.0359 for 3177 Fo > 4sig(Fo) and 0.0424 for all 3697 data REM 211 parameters refined using 0 restraints END WGHT 0.0439 0.5107 REM Highest difference peak 0.312, deepest hole -0.207, 1-sigma level 0.038 Q1 1 0.4244 0.3043 0.1326 11.00000 0.05 0.31 Q2 1 0.3166 0.7008 0.1671 11.00000 0.05 0.30 Q3 1 0.3575 0.3709 0.1489 11.00000 0.05 0.30 Q4 1 0.4219 0.2821 0.1998 11.00000 0.05 0.30 Q5 1 0.4855 0.1779 0.2513 11.00000 0.05 0.29 Q6 1 0.3828 0.6466 0.2262 11.00000 0.05 0.27 Q7 1 0.4602 0.5616 0.2266 11.00000 0.05 0.26 Q8 1 0.7096 0.0552 0.3760 11.00000 0.05 0.25 Q9 1 0.2961 0.6428 0.1030 11.00000 0.05 0.24 Q10 1 0.4445 0.4238 0.1802 11.00000 0.05 0.24 ; _database_code_depnum_ccdc_archive 'CCDC 943171' ####################################################################### # # 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_16b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 O5' _chemical_formula_sum 'C18 H24 O5' _chemical_formula_weight 320.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.6092(10) _cell_length_b 13.7840(15) _cell_length_c 13.9589(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1656.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5660 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.22 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15977 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 28.40 _reflns_number_total 2162 _reflns_number_gt 1949 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0410P)^2^+0.1658P] 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; 1978 Freidel pairs merged' _refine_ls_abs_structure_Flack ? _chemical_absolute_configuration unk _refine_ls_number_reflns 2162 _refine_ls_number_parameters 211 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.12677(18) 0.27722(11) 0.13847(11) 0.0247(3) Uani 1 1 d . . . O1 O 0.25804(14) 0.33961(8) 0.13833(8) 0.0265(2) Uani 1 1 d . . . C2 C 0.38921(19) 0.28414(13) 0.10224(12) 0.0306(4) Uani 1 1 d . . . H2 H 0.3997 0.2972 0.0321 0.037 Uiso 1 1 calc R . . C3 C 0.3312(2) 0.18038(13) 0.11519(14) 0.0339(4) Uani 1 1 d . . . H3 H 0.3861 0.1350 0.0707 0.041 Uiso 1 1 calc R . . O2 O 0.17109(14) 0.19308(8) 0.08716(9) 0.0306(3) Uani 1 1 d . . . C4 C 0.3314(2) 0.14126(13) 0.21703(15) 0.0363(4) Uani 1 1 d . . . H4A H 0.4400 0.1354 0.2396 0.044 Uiso 1 1 calc R . . H4B H 0.2849 0.0756 0.2173 0.044 Uiso 1 1 calc R . . C5 C 0.2407(2) 0.20654(12) 0.28629(12) 0.0297(3) Uani 1 1 d . . . H5A H 0.3079 0.2614 0.3056 0.036 Uiso 1 1 calc R . . H5B H 0.2156 0.1689 0.3447 0.036 Uiso 1 1 calc R . . C6 C 0.08803(18) 0.24750(11) 0.24356(11) 0.0251(3) Uani 1 1 d . . . O3 O 0.00040(13) 0.31967(9) 0.09548(8) 0.0284(2) Uani 1 1 d . . . C7 C 0.0279(2) 0.35241(15) -0.00113(12) 0.0364(4) Uani 1 1 d . . . H7A H 0.1231 0.3914 -0.0029 0.055 Uiso 1 1 calc R . . H7B H -0.0600 0.3919 -0.0226 0.055 Uiso 1 1 calc R . . H7C H 0.0395 0.2962 -0.0435 0.055 Uiso 1 1 calc R . . C8 C 0.5386(2) 0.31474(15) 0.15111(15) 0.0388(4) Uani 1 1 d . . . H8A H 0.6215 0.2675 0.1356 0.047 Uiso 1 1 calc R . . H8B H 0.5232 0.3143 0.2214 0.047 Uiso 1 1 calc R . . C9 C 0.5894(2) 0.41552(18) 0.11965(16) 0.0491(5) Uani 1 1 d . . . H9A H 0.5937 0.4182 0.0495 0.074 Uiso 1 1 calc R . . H9B H 0.6924 0.4297 0.1460 0.074 Uiso 1 1 calc R . . H9C H 0.5147 0.4637 0.1431 0.074 Uiso 1 1 calc R . . C10 C -0.0459(2) 0.17206(12) 0.24181(12) 0.0287(3) Uani 1 1 d . . . H10A H -0.1365 0.2017 0.2094 0.034 Uiso 1 1 calc R . . H10B H -0.0124 0.1160 0.2026 0.034 Uiso 1 1 calc R . . C11 C -0.09789(19) 0.13484(12) 0.33881(13) 0.0281(3) Uani 1 1 d . . . C12 C -0.03732(19) 0.04892(11) 0.37708(14) 0.0318(4) Uani 1 1 d . . . H12 H 0.0404 0.0144 0.3428 0.038 Uiso 1 1 calc R . . C13 C -0.0895(2) 0.01333(14) 0.46468(14) 0.0366(4) Uani 1 1 d . . . H13 H -0.0494 -0.0461 0.4887 0.044 Uiso 1 1 calc R . . C14 C -0.1988(2) 0.06377(14) 0.51671(14) 0.0376(4) Uani 1 1 d . . . H14 H -0.2324 0.0400 0.5772 0.045 Uiso 1 1 calc R . . C15 C -0.2596(2) 0.14927(14) 0.48051(15) 0.0381(4) Uani 1 1 d . . . H15 H -0.3350 0.1844 0.5162 0.046 Uiso 1 1 calc R . . C16 C -0.2104(2) 0.18364(12) 0.39215(14) 0.0339(4) Uani 1 1 d . . . H16 H -0.2544 0.2417 0.3674 0.041 Uiso 1 1 calc R . . C17 C 0.0411(2) 0.33703(12) 0.30166(11) 0.0263(3) Uani 1 1 d . . . O4 O 0.11936(15) 0.37409(9) 0.36295(10) 0.0379(3) Uani 1 1 d . . . O5 O -0.09904(15) 0.37029(9) 0.27683(9) 0.0354(3) Uani 1 1 d . . . C18 C -0.1524(3) 0.45622(15) 0.32650(15) 0.0452(5) Uani 1 1 d . . . H18A H -0.1510 0.4445 0.3957 0.068 Uiso 1 1 calc R . . H18B H -0.2586 0.4715 0.3061 0.068 Uiso 1 1 calc R . . H18C H -0.0839 0.5108 0.3112 0.068 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 0.0271(7) 0.0272(7) 0.0197(7) -0.0018(6) -0.0018(6) 0.0011(6) O1 0.0263(5) 0.0293(5) 0.0239(6) -0.0003(5) 0.0013(5) 0.0003(4) C2 0.0289(8) 0.0382(9) 0.0247(8) -0.0008(7) 0.0023(6) 0.0054(7) C3 0.0341(9) 0.0345(9) 0.0330(9) -0.0061(7) 0.0016(7) 0.0077(7) O2 0.0344(6) 0.0310(6) 0.0265(6) -0.0082(5) 0.0000(5) 0.0020(5) C4 0.0382(10) 0.0312(8) 0.0394(10) 0.0048(7) -0.0034(8) 0.0070(8) C5 0.0326(8) 0.0304(8) 0.0261(8) 0.0046(6) -0.0048(7) 0.0012(7) C6 0.0289(7) 0.0249(7) 0.0214(7) 0.0002(6) -0.0029(6) 0.0001(6) O3 0.0288(6) 0.0371(6) 0.0192(5) 0.0019(5) -0.0023(4) 0.0023(5) C7 0.0399(10) 0.0475(11) 0.0218(8) 0.0071(7) -0.0032(7) 0.0004(8) C8 0.0303(9) 0.0518(11) 0.0342(9) 0.0025(9) -0.0007(7) 0.0040(8) C9 0.0443(10) 0.0653(13) 0.0375(10) 0.0058(10) -0.0024(9) -0.0176(10) C10 0.0336(8) 0.0282(7) 0.0243(7) -0.0020(6) -0.0018(7) -0.0039(6) C11 0.0294(8) 0.0274(8) 0.0273(8) -0.0012(6) -0.0018(6) -0.0063(6) C12 0.0305(8) 0.0268(7) 0.0380(9) -0.0014(7) 0.0004(7) -0.0030(6) C13 0.0345(9) 0.0313(9) 0.0442(11) 0.0114(8) -0.0050(8) -0.0058(7) C14 0.0361(10) 0.0445(10) 0.0323(9) 0.0080(8) 0.0001(8) -0.0111(8) C15 0.0361(9) 0.0394(9) 0.0387(10) 0.0013(8) 0.0072(8) -0.0026(8) C16 0.0351(9) 0.0305(8) 0.0360(9) 0.0049(8) 0.0020(8) 0.0015(7) C17 0.0354(8) 0.0252(8) 0.0183(7) 0.0013(6) 0.0025(6) -0.0032(6) O4 0.0435(7) 0.0404(7) 0.0298(6) -0.0107(6) -0.0030(5) -0.0067(5) O5 0.0411(7) 0.0368(7) 0.0283(6) -0.0083(5) -0.0028(5) 0.0105(5) C18 0.0614(13) 0.0402(10) 0.0339(9) -0.0075(8) 0.0054(9) 0.0172(9) _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 O3 1.3734(19) . ? C1 O2 1.4155(18) . ? C1 O1 1.4201(19) . ? C1 C6 1.559(2) . ? O1 C2 1.454(2) . ? C2 C8 1.515(3) . ? C2 C3 1.526(3) . ? C3 O2 1.444(2) . ? C3 C4 1.520(3) . ? C4 C5 1.534(3) . ? C5 C6 1.550(2) . ? C6 C17 1.531(2) . ? C6 C10 1.553(2) . ? O3 C7 1.442(2) . ? C8 C9 1.521(3) . ? C10 C11 1.515(2) . ? C11 C16 1.395(3) . ? C11 C12 1.400(2) . ? C12 C13 1.392(3) . ? C13 C14 1.377(3) . ? C14 C15 1.385(3) . ? C15 C16 1.387(3) . ? C17 O4 1.203(2) . ? C17 O5 1.337(2) . ? O5 C18 1.447(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 O3 C1 O2 109.97(13) . . ? O3 C1 O1 111.83(12) . . ? O2 C1 O1 106.32(12) . . ? O3 C1 C6 110.70(13) . . ? O2 C1 C6 108.57(12) . . ? O1 C1 C6 109.31(12) . . ? C1 O1 C2 107.47(11) . . ? O1 C2 C8 110.91(14) . . ? O1 C2 C3 101.41(13) . . ? C8 C2 C3 119.03(15) . . ? O2 C3 C4 107.31(15) . . ? O2 C3 C2 99.60(14) . . ? C4 C3 C2 116.28(15) . . ? C1 O2 C3 102.69(12) . . ? C3 C4 C5 112.36(14) . . ? C4 C5 C6 113.76(14) . . ? C17 C6 C5 108.27(13) . . ? C17 C6 C10 110.63(13) . . ? C5 C6 C10 113.07(13) . . ? C17 C6 C1 110.06(13) . . ? C5 C6 C1 106.04(13) . . ? C10 C6 C1 108.66(12) . . ? C1 O3 C7 114.31(14) . . ? C2 C8 C9 111.60(16) . . ? C11 C10 C6 115.59(13) . . ? C16 C11 C12 117.58(16) . . ? C16 C11 C10 121.25(15) . . ? C12 C11 C10 121.15(16) . . ? C13 C12 C11 120.87(17) . . ? C14 C13 C12 120.39(17) . . ? C13 C14 C15 119.69(18) . . ? C14 C15 C16 119.97(18) . . ? C15 C16 C11 121.46(16) . . ? O4 C17 O5 122.99(16) . . ? O4 C17 C6 124.85(16) . . ? O5 C17 C6 112.16(14) . . ? C17 O5 C18 116.31(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 O3 C1 O1 C2 -130.62(13) . . . . ? O2 C1 O1 C2 -10.57(16) . . . . ? C6 C1 O1 C2 106.44(14) . . . . ? C1 O1 C2 C8 -145.69(14) . . . . ? C1 O1 C2 C3 -18.32(16) . . . . ? O1 C2 C3 O2 39.61(15) . . . . ? C8 C2 C3 O2 161.50(15) . . . . ? O1 C2 C3 C4 -75.23(17) . . . . ? C8 C2 C3 C4 46.7(2) . . . . ? O3 C1 O2 C3 158.23(13) . . . . ? O1 C1 O2 C3 36.99(16) . . . . ? C6 C1 O2 C3 -80.51(15) . . . . ? C4 C3 O2 C1 74.59(16) . . . . ? C2 C3 O2 C1 -46.95(15) . . . . ? O2 C3 C4 C5 -55.5(2) . . . . ? C2 C3 C4 C5 54.9(2) . . . . ? C3 C4 C5 C6 40.5(2) . . . . ? C4 C5 C6 C17 -159.57(14) . . . . ? C4 C5 C6 C10 77.49(18) . . . . ? C4 C5 C6 C1 -41.48(17) . . . . ? O3 C1 C6 C17 -59.78(17) . . . . ? O2 C1 C6 C17 179.41(13) . . . . ? O1 C1 C6 C17 63.83(16) . . . . ? O3 C1 C6 C5 -176.67(12) . . . . ? O2 C1 C6 C5 62.52(15) . . . . ? O1 C1 C6 C5 -53.06(16) . . . . ? O3 C1 C6 C10 61.50(16) . . . . ? O2 C1 C6 C10 -59.31(16) . . . . ? O1 C1 C6 C10 -174.89(12) . . . . ? O2 C1 O3 C7 -62.02(17) . . . . ? O1 C1 O3 C7 55.86(17) . . . . ? C6 C1 O3 C7 178.01(14) . . . . ? O1 C2 C8 C9 -70.6(2) . . . . ? C3 C2 C8 C9 172.38(17) . . . . ? C17 C6 C10 C11 -59.34(19) . . . . ? C5 C6 C10 C11 62.29(19) . . . . ? C1 C6 C10 C11 179.73(14) . . . . ? C6 C10 C11 C16 87.1(2) . . . . ? C6 C10 C11 C12 -94.49(19) . . . . ? C16 C11 C12 C13 0.8(2) . . . . ? C10 C11 C12 C13 -177.74(15) . . . . ? C11 C12 C13 C14 -1.9(3) . . . . ? C12 C13 C14 C15 1.5(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C11 -1.2(3) . . . . ? C12 C11 C16 C15 0.8(3) . . . . ? C10 C11 C16 C15 179.29(16) . . . . ? C5 C6 C17 O4 7.2(2) . . . . ? C10 C6 C17 O4 131.62(17) . . . . ? C1 C6 C17 O4 -108.28(18) . . . . ? C5 C6 C17 O5 -172.62(13) . . . . ? C10 C6 C17 O5 -48.20(18) . . . . ? C1 C6 C17 O5 71.89(17) . . . . ? O4 C17 O5 C18 1.4(2) . . . . ? C6 C17 O5 C18 -178.76(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.191 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.029 _iucr_refine_instruction_details ; TITL 16b in Pca2(1) CELL 0.71073 8.6092 13.7840 13.9589 90.000 90.000 90.000 ZERR 4.00 0.0010 0.0015 0.0015 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, -Y, Z SYMM 0.5-X, Y, 0.5+Z SFAC C H O UNIT 72 96 20 TEMP -123 SIZE 0.16 0.44 0.63 ACTA CONF WPDB -1 OMIT 0 1 0 MERG 4 L.S. 6 BOND FMAP 2 PLAN 10 REM EXTI 0.000000 INSIG. WGHT 0.041000 0.165800 FVAR 0.23308 C1 1 0.126775 0.277221 0.138466 11.00000 0.02713 0.02716 = 0.01973 -0.00183 -0.00177 0.00113 O1 3 0.258040 0.339611 0.138330 11.00000 0.02630 0.02933 = 0.02388 -0.00034 0.00126 0.00034 C2 1 0.389213 0.284142 0.102244 11.00000 0.02886 0.03816 = 0.02471 -0.00082 0.00234 0.00541 AFIX 13 H2 2 0.399656 0.297220 0.032073 11.00000 -1.20000 AFIX 0 C3 1 0.331214 0.180379 0.115188 11.00000 0.03407 0.03453 = 0.03300 -0.00607 0.00164 0.00766 AFIX 13 H3 2 0.386051 0.134997 0.070690 11.00000 -1.20000 AFIX 0 O2 3 0.171091 0.193080 0.087162 11.00000 0.03440 0.03097 = 0.02651 -0.00817 0.00000 0.00203 C4 1 0.331428 0.141262 0.217032 11.00000 0.03822 0.03121 = 0.03938 0.00479 -0.00338 0.00697 AFIX 23 H4A 2 0.440033 0.135442 0.239621 11.00000 -1.20000 H4B 2 0.284905 0.075581 0.217326 11.00000 -1.20000 AFIX 0 C5 1 0.240687 0.206543 0.286288 11.00000 0.03261 0.03037 = 0.02614 0.00464 -0.00484 0.00120 AFIX 23 H5A 2 0.307906 0.261422 0.305640 11.00000 -1.20000 H5B 2 0.215561 0.168893 0.344662 11.00000 -1.20000 AFIX 0 C6 1 0.088026 0.247499 0.243564 11.00000 0.02891 0.02486 = 0.02140 0.00020 -0.00290 0.00009 O3 3 0.000403 0.319675 0.095480 11.00000 0.02881 0.03709 = 0.01916 0.00187 -0.00233 0.00231 C7 1 0.027948 0.352412 -0.001126 11.00000 0.03985 0.04747 = 0.02181 0.00714 -0.00320 0.00036 AFIX 137 H7A 2 0.123085 0.391407 -0.002941 11.00000 -1.50000 H7B 2 -0.060037 0.391914 -0.022635 11.00000 -1.50000 H7C 2 0.039522 0.296168 -0.043474 11.00000 -1.50000 AFIX 0 C8 1 0.538575 0.314735 0.151108 11.00000 0.03030 0.05184 = 0.03419 0.00252 -0.00073 0.00404 AFIX 23 H8A 2 0.621479 0.267490 0.135644 11.00000 -1.20000 H8B 2 0.523175 0.314265 0.221390 11.00000 -1.20000 AFIX 0 C9 1 0.589364 0.415518 0.119648 11.00000 0.04434 0.06531 = 0.03753 0.00585 -0.00236 -0.01756 AFIX 137 H9A 2 0.593708 0.418172 0.049542 11.00000 -1.50000 H9B 2 0.692391 0.429661 0.146034 11.00000 -1.50000 H9C 2 0.514713 0.463651 0.143100 11.00000 -1.50000 AFIX 0 C10 1 -0.045910 0.172058 0.241812 11.00000 0.03359 0.02825 = 0.02430 -0.00200 -0.00181 -0.00385 AFIX 23 H10A 2 -0.136495 0.201743 0.209418 11.00000 -1.20000 H10B 2 -0.012414 0.115971 0.202623 11.00000 -1.20000 AFIX 0 C11 1 -0.097895 0.134841 0.338805 11.00000 0.02943 0.02741 = 0.02734 -0.00125 -0.00177 -0.00628 C12 1 -0.037317 0.048920 0.377075 11.00000 0.03055 0.02681 = 0.03800 -0.00140 0.00037 -0.00298 AFIX 43 H12 2 0.040419 0.014447 0.342806 11.00000 -1.20000 AFIX 0 C13 1 -0.089490 0.013335 0.464680 11.00000 0.03448 0.03128 = 0.04417 0.01139 -0.00500 -0.00583 AFIX 43 H13 2 -0.049444 -0.046095 0.488718 11.00000 -1.20000 AFIX 0 C14 1 -0.198823 0.063773 0.516715 11.00000 0.03610 0.04446 = 0.03234 0.00804 0.00005 -0.01108 AFIX 43 H14 2 -0.232381 0.040030 0.577160 11.00000 -1.20000 AFIX 0 C15 1 -0.259616 0.149271 0.480508 11.00000 0.03614 0.03944 = 0.03874 0.00129 0.00721 -0.00263 AFIX 43 H15 2 -0.334964 0.184368 0.516160 11.00000 -1.20000 AFIX 0 C16 1 -0.210432 0.183641 0.392150 11.00000 0.03513 0.03051 = 0.03599 0.00487 0.00197 0.00155 AFIX 43 H16 2 -0.254374 0.241695 0.367435 11.00000 -1.20000 AFIX 0 C17 1 0.041121 0.337033 0.301662 11.00000 0.03537 0.02522 = 0.01826 0.00130 0.00250 -0.00323 O4 3 0.119363 0.374095 0.362952 11.00000 0.04345 0.04035 = 0.02981 -0.01066 -0.00299 -0.00673 O5 3 -0.099040 0.370291 0.276827 11.00000 0.04114 0.03683 = 0.02829 -0.00834 -0.00277 0.01055 C18 1 -0.152442 0.456219 0.326496 11.00000 0.06140 0.04025 = 0.03388 -0.00754 0.00541 0.01716 AFIX 137 H18A 2 -0.150993 0.444486 0.395734 11.00000 -1.50000 H18B 2 -0.258596 0.471511 0.306139 11.00000 -1.50000 H18C 2 -0.083894 0.510838 0.311246 11.00000 -1.50000 HKLF 4 REM 16b in Pca2(1) REM R1 = 0.0278 for 1949 Fo > 4sig(Fo) and 0.0334 for all 2162 data REM 211 parameters refined using 1 restraints END WGHT 0.0410 0.1657 REM Highest difference peak 0.191, deepest hole -0.138, 1-sigma level 0.029 Q1 1 0.0561 0.2845 0.2798 11.00000 0.05 0.19 Q2 1 0.1593 0.2227 0.2659 11.00000 0.05 0.17 Q3 1 0.3732 0.2335 0.1165 11.00000 0.05 0.16 Q4 1 -0.0452 0.1037 0.3667 11.00000 0.05 0.15 Q5 1 0.1034 0.2646 0.1990 11.00000 0.05 0.15 Q6 1 0.0258 0.2179 0.2406 11.00000 0.05 0.15 Q7 1 0.2521 0.1832 0.1039 11.00000 0.05 0.14 Q8 1 0.4570 0.3054 0.1370 11.00000 0.05 0.13 Q9 1 0.1507 0.2327 0.1110 11.00000 0.05 0.13 Q10 1 -0.0669 0.4870 0.3688 11.00000 0.05 0.12 ; #===END _database_code_depnum_ccdc_archive 'CCDC 943172'