# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 889494' #TrackingRef 'mo_120507e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Br O5' _chemical_formula_weight 441.27 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 11.756 _cell_length_b 14.575 _cell_length_c 11.520 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1973.9 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2202 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 18.98 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6673 _exptl_absorpt_correction_T_max 0.8165 _exptl_absorpt_process_details 'SADABS, Sheldrick,1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14075 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.48 _reflns_number_total 3918 _reflns_number_gt 2297 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(11) _refine_ls_number_reflns 3918 _refine_ls_number_parameters 271 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 1.006 _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 Br1 Br 0.42547(4) 0.15193(3) 0.87553(5) 0.0814(2) Uani 1 1 d . . . C1 C 0.5436(4) 0.1595(3) 0.7633(4) 0.0611(12) Uani 1 1 d . . . C2 C 0.6549(5) 0.1671(3) 0.8011(4) 0.0793(15) Uani 1 1 d . . . H2 H 0.6715 0.1673 0.8801 0.095 Uiso 1 1 calc R . . C3 C 0.7398(5) 0.1744(4) 0.7214(5) 0.0850(17) Uani 1 1 d . . . H3 H 0.8150 0.1789 0.7459 0.102 Uiso 1 1 calc R . . C4 C 0.7149(4) 0.1752(3) 0.6045(5) 0.0625(12) Uani 1 1 d . . . C5 C 0.6031(4) 0.1664(2) 0.5655(4) 0.0497(11) Uani 1 1 d . . . C6 C 0.5180(4) 0.1574(2) 0.6478(4) 0.0514(10) Uani 1 1 d . . . H6 H 0.4429 0.1500 0.6242 0.062 Uiso 1 1 calc R . . C7 C 0.5833(3) 0.1657(3) 0.4352(3) 0.0454(10) Uani 1 1 d . . . H7 H 0.5729 0.2292 0.4093 0.054 Uiso 1 1 calc R . . C8 C 0.6866(3) 0.1273(2) 0.3755(5) 0.0510(9) Uani 1 1 d . . . C9 C 0.7976(4) 0.1579(3) 0.4158(5) 0.0628(13) Uani 1 1 d . . . C10 C 0.4773(3) 0.1111(3) 0.4018(3) 0.0494(11) Uani 1 1 d . . . H10A H 0.4760 0.0541 0.4454 0.059 Uiso 1 1 calc R . . H10B H 0.4101 0.1459 0.4226 0.059 Uiso 1 1 calc R . . C11 C 0.4743(4) 0.0902(3) 0.2763(4) 0.0517(10) Uani 1 1 d . . . C12 C 0.6776(3) 0.0723(3) 0.2831(4) 0.0557(11) Uani 1 1 d . . . C13 C 0.7661(2) 0.01794(19) 0.2249(3) 0.0700(14) Uani 1 1 d G . . C14 C 0.8453(3) -0.0315(2) 0.2889(3) 0.0909(18) Uani 1 1 d G . . H14 H 0.8451 -0.0280 0.3695 0.109 Uiso 1 1 calc R . . C15 C 0.9248(3) -0.0863(2) 0.2325(5) 0.125(3) Uani 1 1 d G . . H15 H 0.9778 -0.1193 0.2754 0.150 Uiso 1 1 calc R . . C16 C 0.9251(3) -0.0915(3) 0.1121(5) 0.152(5) Uani 1 1 d G . . H16 H 0.9783 -0.1281 0.0743 0.182 Uiso 1 1 calc R . . C17 C 0.8459(4) -0.0420(3) 0.0480(3) 0.148(4) Uani 1 1 d G . . H17 H 0.8461 -0.0456 -0.0326 0.177 Uiso 1 1 calc R . . C18 C 0.7664(3) 0.0127(3) 0.1044(3) 0.104(2) Uani 1 1 d G . . H18 H 0.7134 0.0458 0.0615 0.125 Uiso 1 1 calc R . . C19 C 0.3886(4) 0.0953(3) 0.2011(4) 0.0646(12) Uani 1 1 d . A . H19 H 0.4028 0.0774 0.1250 0.078 Uiso 1 1 calc R . . C20 C 0.2735(4) 0.1271(4) 0.2289(4) 0.0739(14) Uani 1 1 d D . . O1 O 0.8047(3) 0.1873(2) 0.5282(3) 0.0758(9) Uani 1 1 d . . . O2 O 0.8846(3) 0.1621(2) 0.3619(5) 0.0866(12) Uani 1 1 d . . . O3 O 0.5746(2) 0.0564(2) 0.2300(3) 0.0626(8) Uani 1 1 d . . . O4 O 0.2371(3) 0.1517(3) 0.3208(3) 0.0824(10) Uani 1 1 d . A . C21 C 0.0917(12) 0.1628(17) 0.1622(15) 0.107(7) Uani 0.529(15) 1 d PD A 1 H21A H 0.0670 0.1184 0.2198 0.129 Uiso 0.529(15) 1 calc PR A 1 H21B H 0.0826 0.2237 0.1947 0.129 Uiso 0.529(15) 1 calc PR A 1 C22 C 0.0224(9) 0.1539(10) 0.0577(12) 0.099(5) Uani 0.529(15) 1 d PD A 1 H22A H 0.0552 0.1898 -0.0035 0.148 Uiso 0.529(15) 1 calc PR A 1 H22B H -0.0533 0.1753 0.0734 0.148 Uiso 0.529(15) 1 calc PR A 1 H22C H 0.0196 0.0906 0.0345 0.148 Uiso 0.529(15) 1 calc PR A 1 O5 O 0.2121(11) 0.1468(13) 0.1328(10) 0.118(6) Uani 0.529(15) 1 d PD A 1 C21' C 0.0854(13) 0.1135(10) 0.140(3) 0.107(8) Uani 0.471(15) 1 d PD A 2 H21C H 0.0519 0.1013 0.2153 0.129 Uiso 0.471(15) 1 calc PR A 2 H21D H 0.0468 0.0771 0.0814 0.129 Uiso 0.471(15) 1 calc PR A 2 C22' C 0.0825(16) 0.2140(9) 0.1109(18) 0.112(7) Uani 0.471(15) 1 d PD A 2 H22D H 0.1267 0.2474 0.1668 0.168 Uiso 0.471(15) 1 calc PR A 2 H22E H 0.0053 0.2354 0.1126 0.168 Uiso 0.471(15) 1 calc PR A 2 H22F H 0.1137 0.2234 0.0348 0.168 Uiso 0.471(15) 1 calc PR A 2 O5' O 0.2087(11) 0.0958(9) 0.1401(11) 0.080(4) Uani 0.471(15) 1 d PD A 2 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 Br1 0.1086(4) 0.0827(3) 0.0529(2) -0.0032(4) 0.0044(4) -0.0066(3) C1 0.075(3) 0.052(2) 0.056(3) -0.004(2) -0.008(2) 0.001(2) C2 0.088(4) 0.091(4) 0.058(3) -0.007(3) -0.026(3) 0.013(3) C3 0.073(4) 0.103(4) 0.079(4) -0.020(3) -0.031(3) 0.011(3) C4 0.055(3) 0.062(3) 0.072(3) -0.009(2) -0.011(3) 0.007(2) C5 0.054(3) 0.038(2) 0.057(3) 0.0016(19) -0.008(2) 0.0048(18) C6 0.050(3) 0.048(2) 0.056(2) -0.004(2) -0.008(2) 0.005(2) C7 0.034(2) 0.046(2) 0.055(2) 0.0007(17) -0.0015(18) 0.0019(18) C8 0.046(2) 0.0438(19) 0.063(2) -0.003(3) 0.000(3) 0.0024(15) C9 0.041(3) 0.058(2) 0.089(4) -0.006(3) -0.003(2) 0.003(2) C10 0.043(2) 0.056(2) 0.049(3) 0.005(2) -0.001(2) 0.0093(18) C11 0.047(2) 0.053(2) 0.055(2) -0.001(2) 0.010(2) -0.001(2) C12 0.038(3) 0.053(2) 0.076(3) 0.002(2) 0.006(2) 0.0005(19) C13 0.057(3) 0.052(3) 0.101(4) -0.028(3) 0.023(3) -0.009(2) C14 0.063(3) 0.058(3) 0.151(5) 0.003(3) 0.022(4) 0.015(3) C15 0.075(4) 0.061(4) 0.239(10) 0.001(5) 0.038(5) 0.011(3) C16 0.106(6) 0.109(6) 0.241(13) -0.093(8) 0.093(7) -0.051(5) C17 0.095(5) 0.188(9) 0.161(8) -0.109(7) 0.037(5) -0.047(5) C18 0.070(4) 0.131(5) 0.110(5) -0.062(4) 0.023(3) -0.014(3) C19 0.047(3) 0.100(3) 0.047(2) -0.009(3) -0.001(2) -0.004(3) C20 0.046(3) 0.122(4) 0.053(3) -0.005(3) -0.012(3) 0.003(3) O1 0.0472(19) 0.093(2) 0.087(2) -0.018(2) -0.0087(19) -0.0083(16) O2 0.0493(18) 0.094(2) 0.117(3) -0.015(3) 0.019(3) -0.0037(16) O3 0.0545(19) 0.0739(19) 0.0593(17) -0.0156(15) 0.0027(15) 0.0047(15) O4 0.058(2) 0.121(3) 0.068(2) -0.014(2) 0.0026(17) 0.0058(18) C21 0.098(12) 0.12(2) 0.104(14) -0.007(13) -0.005(9) 0.002(12) C22 0.076(8) 0.085(9) 0.135(13) 0.007(8) -0.022(8) 0.007(7) O5 0.069(7) 0.204(16) 0.082(7) -0.036(9) -0.036(6) 0.072(9) C21' 0.098(15) 0.119(18) 0.104(16) -0.007(14) -0.005(11) 0.002(12) C22' 0.133(16) 0.096(11) 0.106(13) 0.029(10) 0.017(11) 0.027(11) O5' 0.052(6) 0.111(10) 0.078(6) -0.002(6) -0.009(5) 0.017(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 Br1 C1 1.901(5) . ? C1 C6 1.365(6) . ? C1 C2 1.384(7) . ? C2 C3 1.360(8) . ? C2 H2 0.9300 . ? C3 C4 1.378(7) . ? C3 H3 0.9300 . ? C4 O1 1.385(6) . ? C4 C5 1.395(6) . ? C5 C6 1.385(6) . ? C5 C7 1.519(6) . ? C6 H6 0.9300 . ? C7 C8 1.504(5) . ? C7 C10 1.528(5) . ? C7 H7 0.9800 . ? C8 C12 1.337(7) . ? C8 C9 1.454(6) . ? C9 O2 1.199(6) . ? C9 O1 1.366(6) . ? C10 C11 1.478(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C19 1.331(6) . ? C11 O3 1.385(5) . ? C12 O3 1.376(5) . ? C12 C13 1.469(5) . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C14 C15 1.3900 . ? C14 H14 0.9300 . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 C17 1.3900 . ? C16 H16 0.9300 . ? C17 C18 1.3900 . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.465(7) . ? C19 H19 0.9300 . ? C20 O4 1.197(5) . ? C20 O5 1.352(8) . ? C20 O5' 1.355(9) . ? C21 C22 1.459(10) . ? C21 O5 1.475(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C21' O5' 1.471(9) . ? C21' C22' 1.504(10) . ? C21' H21C 0.9700 . ? C21' H21D 0.9700 . ? C22' H22D 0.9600 . ? C22' H22E 0.9600 . ? C22' H22F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.2(5) . . ? C6 C1 Br1 120.0(4) . . ? C2 C1 Br1 118.8(4) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 O1 117.4(5) . . ? C3 C4 C5 121.0(5) . . ? O1 C4 C5 121.6(4) . . ? C6 C5 C4 117.9(4) . . ? C6 C5 C7 124.4(4) . . ? C4 C5 C7 117.6(4) . . ? C1 C6 C5 120.4(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C5 109.3(4) . . ? C8 C7 C10 110.4(3) . . ? C5 C7 C10 112.1(3) . . ? C8 C7 H7 108.3 . . ? C5 C7 H7 108.3 . . ? C10 C7 H7 108.3 . . ? C12 C8 C9 120.6(4) . . ? C12 C8 C7 121.6(4) . . ? C9 C8 C7 117.6(4) . . ? O2 C9 O1 115.0(5) . . ? O2 C9 C8 128.0(5) . . ? O1 C9 C8 117.0(5) . . ? C11 C10 C7 111.9(3) . . ? C11 C10 H10A 109.2 . . ? C7 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C7 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C19 C11 O3 114.5(4) . . ? C19 C11 C10 130.1(4) . . ? O3 C11 C10 115.4(4) . . ? C8 C12 O3 121.6(4) . . ? C8 C12 C13 129.1(4) . . ? O3 C12 C13 109.2(4) . . ? C14 C13 C18 120.0 . . ? C14 C13 C12 120.7(3) . . ? C18 C13 C12 119.2(3) . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.0 . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C11 C19 C20 125.0(4) . . ? C11 C19 H19 117.5 . . ? C20 C19 H19 117.5 . . ? O4 C20 O5 118.1(8) . . ? O4 C20 O5' 124.6(8) . . ? O5 C20 O5' 32.1(8) . . ? O4 C20 C19 128.2(4) . . ? O5 C20 C19 112.3(7) . . ? O5' C20 C19 104.3(7) . . ? C9 O1 C4 121.0(4) . . ? C12 O3 C11 121.3(3) . . ? C22 C21 O5 109.4(10) . . ? C22 C21 H21A 109.8 . . ? O5 C21 H21A 109.8 . . ? C22 C21 H21B 109.8 . . ? O5 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? C20 O5 C21 111.0(11) . . ? O5' C21' C22' 101.2(11) . . ? O5' C21' H21C 111.5 . . ? C22' C21' H21C 111.5 . . ? O5' C21' H21D 111.5 . . ? C22' C21' H21D 111.5 . . ? H21C C21' H21D 109.4 . . ? C21' C22' H22D 109.5 . . ? C21' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C21' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? C20 O5' C21' 119.7(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 C6 C1 C2 C3 1.2(7) . . . . ? Br1 C1 C2 C3 -178.7(4) . . . . ? C1 C2 C3 C4 0.7(8) . . . . ? C2 C3 C4 O1 176.9(4) . . . . ? C2 C3 C4 C5 -1.5(8) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? O1 C4 C5 C6 -178.0(4) . . . . ? C3 C4 C5 C7 -178.7(4) . . . . ? O1 C4 C5 C7 2.9(6) . . . . ? C2 C1 C6 C5 -2.4(6) . . . . ? Br1 C1 C6 C5 177.6(3) . . . . ? C4 C5 C6 C1 1.5(6) . . . . ? C7 C5 C6 C1 -179.5(4) . . . . ? C6 C5 C7 C8 -150.1(4) . . . . ? C4 C5 C7 C8 28.9(5) . . . . ? C6 C5 C7 C10 -27.3(5) . . . . ? C4 C5 C7 C10 151.7(4) . . . . ? C5 C7 C8 C12 141.5(4) . . . . ? C10 C7 C8 C12 17.8(6) . . . . ? C5 C7 C8 C9 -43.4(5) . . . . ? C10 C7 C8 C9 -167.2(4) . . . . ? C12 C8 C9 O2 22.2(7) . . . . ? C7 C8 C9 O2 -152.9(5) . . . . ? C12 C8 C9 O1 -159.1(4) . . . . ? C7 C8 C9 O1 25.7(6) . . . . ? C8 C7 C10 C11 -43.1(5) . . . . ? C5 C7 C10 C11 -165.2(3) . . . . ? C7 C10 C11 C19 -136.0(5) . . . . ? C7 C10 C11 O3 46.9(5) . . . . ? C9 C8 C12 O3 -167.5(4) . . . . ? C7 C8 C12 O3 7.4(6) . . . . ? C9 C8 C12 C13 15.1(7) . . . . ? C7 C8 C12 C13 -170.0(4) . . . . ? C8 C12 C13 C14 43.1(5) . . . . ? O3 C12 C13 C14 -134.6(3) . . . . ? C8 C12 C13 C18 -140.2(4) . . . . ? O3 C12 C13 C18 42.1(4) . . . . ? C18 C13 C14 C15 0.0 . . . . ? C12 C13 C14 C15 176.7(3) . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C13 0.0 . . . . ? C14 C13 C18 C17 0.0 . . . . ? C12 C13 C18 C17 -176.8(3) . . . . ? O3 C11 C19 C20 178.8(4) . . . . ? C10 C11 C19 C20 1.8(8) . . . . ? C11 C19 C20 O4 -1.3(9) . . . . ? C11 C19 C20 O5 164.7(10) . . . . ? C11 C19 C20 O5' -162.4(8) . . . . ? O2 C9 O1 C4 -171.5(4) . . . . ? C8 C9 O1 C4 9.6(6) . . . . ? C3 C4 O1 C9 156.8(4) . . . . ? C5 C4 O1 C9 -24.8(6) . . . . ? C8 C12 O3 C11 -5.8(6) . . . . ? C13 C12 O3 C11 172.0(3) . . . . ? C19 C11 O3 C12 159.9(4) . . . . ? C10 C11 O3 C12 -22.6(5) . . . . ? O4 C20 O5 C21 -22.4(19) . . . . ? O5' C20 O5 C21 89(3) . . . . ? C19 C20 O5 C21 170.1(12) . . . . ? C22 C21 O5 C20 -161.6(19) . . . . ? O4 C20 O5' C21' 16.7(17) . . . . ? O5 C20 O5' C21' -72(2) . . . . ? C19 C20 O5' C21' 178.8(12) . . . . ? C22' C21' O5' C20 73(2) . . . . ? 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 C10 H10B O4 0.97 2.35 3.033(5) 127.0 . C17 H17 O4 0.93 2.49 3.217(5) 135.3 2_654 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.220 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.044 data_Ia _database_code_depnum_ccdc_archive 'CCDC 889495' #TrackingRef 'mo_120509b_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Cl O5' _chemical_formula_weight 396.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7129(16) _cell_length_b 10.5113(17) _cell_length_c 10.7041(17) _cell_angle_alpha 107.550(2) _cell_angle_beta 105.744(2) _cell_angle_gamma 98.461(2) _cell_volume 971.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3102 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7083 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3559 _reflns_number_gt 2844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0991P)^2^+0.1387P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3559 _refine_ls_number_parameters 275 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.094 _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 0.7249(2) 0.3583(2) 0.2791(2) 0.0527(5) Uani 1 1 d . . . C2 C 0.6540(3) 0.4576(2) 0.3271(2) 0.0552(6) Uani 1 1 d . . . H2 H 0.7006 0.5506 0.3576 0.066 Uiso 1 1 calc R . . C3 C 0.5140(2) 0.4174(2) 0.3294(2) 0.0482(5) Uani 1 1 d . . . H3 H 0.4654 0.4839 0.3606 0.058 Uiso 1 1 calc R . . C4 C 0.4434(2) 0.27791(19) 0.28546(18) 0.0402(4) Uani 1 1 d . . . C5 C 0.5183(2) 0.1809(2) 0.2373(2) 0.0461(5) Uani 1 1 d . . . H5 H 0.4730 0.0876 0.2073 0.055 Uiso 1 1 calc R . . C6 C 0.6579(2) 0.2207(2) 0.2334(2) 0.0525(5) Uani 1 1 d . . . H6 H 0.7064 0.1549 0.2002 0.063 Uiso 1 1 calc R . . C7 C 0.2919(2) 0.2450(2) 0.2940(2) 0.0443(5) Uani 1 1 d . . . C8 C 0.2117(2) 0.09473(19) 0.26384(19) 0.0405(4) Uani 1 1 d . . . C9 C 0.0596(2) 0.0930(2) 0.2846(2) 0.0497(5) Uani 1 1 d . . . H9A H 0.0162 0.1615 0.2561 0.060 Uiso 1 1 calc R . . H9B H -0.0086 0.0029 0.2340 0.060 Uiso 1 1 calc R . . C10 C 0.1020(2) 0.1282(2) 0.4392(2) 0.0480(5) Uani 1 1 d . . . H10 H 0.0452 0.1638 0.4918 0.058 Uiso 1 1 calc R . . C11 C 0.2306(2) 0.10221(18) 0.49130(19) 0.0401(4) Uani 1 1 d . . . C12 C 0.29314(19) 0.04117(18) 0.37720(17) 0.0361(4) Uani 1 1 d . . . H12 H 0.4003 0.0782 0.4084 0.043 Uiso 1 1 calc R . . C13 C 0.1919(2) 0.0107(2) 0.1153(2) 0.0488(5) Uani 1 1 d . . . C14 C 0.2525(2) -0.11523(18) 0.32111(18) 0.0384(4) Uani 1 1 d . . . C15 C 0.2043(2) -0.1880(2) 0.1793(2) 0.0480(5) Uani 1 1 d . . . C16 C 0.1701(3) -0.3312(2) 0.1242(2) 0.0614(6) Uani 1 1 d . . . H16 H 0.1381 -0.3775 0.0285 0.074 Uiso 1 1 calc R . . C17 C 0.1843(3) -0.4031(2) 0.2126(3) 0.0622(6) Uani 1 1 d . . . H17 H 0.1625 -0.4989 0.1770 0.075 Uiso 1 1 calc R . . C18 C 0.2305(3) -0.3340(2) 0.3538(2) 0.0552(6) Uani 1 1 d . . . H18 H 0.2393 -0.3831 0.4136 0.066 Uiso 1 1 calc R . . C19 C 0.2637(2) -0.1920(2) 0.4071(2) 0.0468(5) Uani 1 1 d . . . H19 H 0.2945 -0.1466 0.5029 0.056 Uiso 1 1 calc R . . C20 C 0.3107(2) 0.12863(19) 0.6392(2) 0.0458(5) Uani 1 1 d . A . C21 C 0.3387(8) 0.2474(8) 0.8711(4) 0.0649(19) Uani 0.740(9) 1 d PD A 1 H21A H 0.4411 0.2902 0.8891 0.078 Uiso 0.740(9) 1 calc PR A 1 H21B H 0.3347 0.1686 0.9005 0.078 Uiso 0.740(9) 1 calc PR A 1 C22 C 0.2670(8) 0.3482(5) 0.9448(4) 0.099(2) Uani 0.740(9) 1 d PD A 1 H22A H 0.2909 0.4334 0.9303 0.149 Uiso 0.740(9) 1 calc PR A 1 H22B H 0.3024 0.3644 1.0425 0.149 Uiso 0.740(9) 1 calc PR A 1 H22C H 0.1618 0.3116 0.9088 0.149 Uiso 0.740(9) 1 calc PR A 1 C22' C 0.406(2) 0.3743(15) 0.9351(13) 0.113(7) Uani 0.260(9) 1 d PD A 2 H22D H 0.4923 0.3595 0.9120 0.169 Uiso 0.260(9) 1 calc PR A 2 H22E H 0.4299 0.4079 1.0343 0.169 Uiso 0.260(9) 1 calc PR A 2 H22F H 0.3694 0.4409 0.8992 0.169 Uiso 0.260(9) 1 calc PR A 2 C21' C 0.288(2) 0.240(2) 0.8717(10) 0.066(6) Uani 0.260(9) 1 d PD A 2 H21C H 0.3257 0.1694 0.9002 0.079 Uiso 0.260(9) 1 calc PR A 2 H21D H 0.2023 0.2517 0.8992 0.079 Uiso 0.260(9) 1 calc PR A 2 Cl1 Cl 0.90346(7) 0.41042(8) 0.28066(9) 0.0855(3) Uani 1 1 d . . . O1 O 0.23310(19) 0.33677(16) 0.3289(2) 0.0697(5) Uani 1 1 d . . . O2 O 0.1761(2) 0.05859(18) 0.02552(15) 0.0662(5) Uani 1 1 d . . . O3 O 0.1901(2) -0.12368(15) 0.08106(14) 0.0620(5) Uani 1 1 d . . . O4 O 0.41794(19) 0.08841(17) 0.67872(15) 0.0633(5) Uani 1 1 d . . . O5 O 0.2519(2) 0.20562(18) 0.72295(15) 0.0675(5) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0462(11) 0.0632(13) 0.0528(12) 0.0279(10) 0.0172(9) 0.0094(10) C2 0.0572(13) 0.0449(11) 0.0605(13) 0.0212(10) 0.0189(10) 0.0008(9) C3 0.0562(12) 0.0378(10) 0.0546(12) 0.0200(9) 0.0204(9) 0.0126(9) C4 0.0450(10) 0.0400(10) 0.0384(9) 0.0207(8) 0.0115(8) 0.0092(8) C5 0.0511(11) 0.0408(10) 0.0486(11) 0.0203(8) 0.0157(9) 0.0112(8) C6 0.0552(12) 0.0532(12) 0.0574(12) 0.0238(10) 0.0242(10) 0.0191(10) C7 0.0487(11) 0.0424(10) 0.0499(11) 0.0270(9) 0.0144(9) 0.0166(9) C8 0.0394(10) 0.0421(10) 0.0404(10) 0.0214(8) 0.0082(7) 0.0064(8) C9 0.0391(10) 0.0553(12) 0.0548(12) 0.0278(10) 0.0085(8) 0.0084(9) C10 0.0454(11) 0.0477(11) 0.0538(12) 0.0200(9) 0.0200(9) 0.0097(9) C11 0.0447(10) 0.0346(9) 0.0405(10) 0.0142(7) 0.0142(8) 0.0071(7) C12 0.0369(9) 0.0357(9) 0.0346(9) 0.0159(7) 0.0079(7) 0.0064(7) C13 0.0487(11) 0.0534(12) 0.0382(10) 0.0215(9) 0.0054(8) 0.0015(9) C14 0.0396(9) 0.0356(9) 0.0401(10) 0.0147(8) 0.0134(7) 0.0066(7) C15 0.0582(12) 0.0428(10) 0.0407(10) 0.0150(8) 0.0153(9) 0.0078(9) C16 0.0799(16) 0.0439(12) 0.0497(12) 0.0073(10) 0.0191(11) 0.0087(11) C17 0.0792(16) 0.0347(10) 0.0724(15) 0.0166(10) 0.0285(13) 0.0127(10) C18 0.0679(14) 0.0421(11) 0.0632(13) 0.0279(10) 0.0226(11) 0.0154(10) C19 0.0513(11) 0.0439(11) 0.0472(11) 0.0214(9) 0.0138(9) 0.0119(9) C20 0.0569(12) 0.0370(10) 0.0433(10) 0.0145(8) 0.0186(9) 0.0076(9) C21 0.087(4) 0.074(4) 0.040(2) 0.018(2) 0.029(2) 0.027(3) C22 0.157(6) 0.098(3) 0.052(2) 0.017(2) 0.040(3) 0.068(4) C22' 0.136(15) 0.113(13) 0.081(9) 0.044(9) 0.027(9) 0.007(10) C21' 0.082(12) 0.076(10) 0.052(7) 0.029(6) 0.041(6) 0.010(8) Cl1 0.0542(4) 0.0991(6) 0.1065(6) 0.0389(5) 0.0367(4) 0.0055(4) O1 0.0625(10) 0.0501(9) 0.1155(15) 0.0393(9) 0.0425(10) 0.0251(8) O2 0.0777(11) 0.0717(11) 0.0425(8) 0.0332(8) 0.0050(7) 0.0007(8) O3 0.0934(12) 0.0507(9) 0.0362(8) 0.0159(7) 0.0173(7) 0.0089(8) O4 0.0708(11) 0.0677(10) 0.0450(8) 0.0173(7) 0.0084(7) 0.0261(9) O5 0.0938(13) 0.0717(11) 0.0426(8) 0.0179(7) 0.0274(8) 0.0341(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 C6 1.371(3) . ? C1 C2 1.381(3) . ? C1 Cl1 1.734(2) . ? C2 C3 1.373(3) . ? C2 H2 0.9300 . ? C3 C4 1.398(3) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 C7 1.495(3) . ? C5 C6 1.375(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.207(2) . ? C7 C8 1.550(3) . ? C8 C13 1.511(3) . ? C8 C9 1.551(3) . ? C8 C12 1.561(2) . ? C9 C10 1.504(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.326(3) . ? C10 H10 0.9300 . ? C11 C20 1.481(3) . ? C11 C12 1.522(3) . ? C12 C14 1.518(2) . ? C12 H12 0.9800 . ? C13 O2 1.198(2) . ? C13 O3 1.344(3) . ? C14 C15 1.384(3) . ? C14 C19 1.389(3) . ? C15 C16 1.391(3) . ? C15 O3 1.400(2) . ? C16 C17 1.371(3) . ? C16 H16 0.9300 . ? C17 C18 1.374(3) . ? C17 H17 0.9300 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O4 1.201(3) . ? C20 O5 1.327(3) . ? C21 O5 1.471(5) . ? C21 C22 1.497(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22' C21' 1.507(10) . ? C22' H22D 0.9600 . ? C22' H22E 0.9600 . ? C22' H22F 0.9600 . ? C21' O5 1.449(10) . ? C21' H21C 0.9700 . ? C21' H21D 0.9700 . ? 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 121.2(2) . . ? C6 C1 Cl1 119.95(18) . . ? C2 C1 Cl1 118.79(17) . . ? C3 C2 C1 119.24(19) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.12(18) . . ? C5 C4 C7 125.13(16) . . ? C3 C4 C7 116.75(17) . . ? C6 C5 C4 121.15(18) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 119.3(2) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? O1 C7 C4 119.82(17) . . ? O1 C7 C8 119.49(18) . . ? C4 C7 C8 120.64(16) . . ? C13 C8 C7 107.80(15) . . ? C13 C8 C9 110.50(15) . . ? C7 C8 C9 109.01(16) . . ? C13 C8 C12 116.17(16) . . ? C7 C8 C12 110.59(14) . . ? C9 C8 C12 102.56(14) . . ? C10 C9 C8 101.28(15) . . ? C10 C9 H9A 111.5 . . ? C8 C9 H9A 111.5 . . ? C10 C9 H9B 111.5 . . ? C8 C9 H9B 111.5 . . ? H9A C9 H9B 109.3 . . ? C11 C10 C9 111.67(18) . . ? C11 C10 H10 124.2 . . ? C9 C10 H10 124.2 . . ? C10 C11 C20 127.24(19) . . ? C10 C11 C12 111.01(17) . . ? C20 C11 C12 121.75(16) . . ? C14 C12 C11 113.04(15) . . ? C14 C12 C8 109.78(14) . . ? C11 C12 C8 100.33(15) . . ? C14 C12 H12 111.1 . . ? C11 C12 H12 111.1 . . ? C8 C12 H12 111.1 . . ? O2 C13 O3 118.18(19) . . ? O2 C13 C8 122.7(2) . . ? O3 C13 C8 119.16(16) . . ? C15 C14 C19 116.90(17) . . ? C15 C14 C12 120.46(16) . . ? C19 C14 C12 122.63(16) . . ? C14 C15 C16 122.10(19) . . ? C14 C15 O3 122.88(18) . . ? C16 C15 O3 115.00(18) . . ? C17 C16 C15 119.2(2) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 121.5(2) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? O4 C20 O5 124.16(19) . . ? O4 C20 C11 124.14(19) . . ? O5 C20 C11 111.68(18) . . ? O5 C21 C22 104.5(5) . . ? O5 C21 H21A 110.9 . . ? C22 C21 H21A 110.9 . . ? O5 C21 H21B 110.9 . . ? C22 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? C21' C22' H22D 109.5 . . ? C21' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C21' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? O5 C21' C22' 104.8(10) . . ? O5 C21' H21C 110.8 . . ? C22' C21' H21C 110.8 . . ? O5 C21' H21D 110.8 . . ? C22' C21' H21D 110.8 . . ? H21C C21' H21D 108.9 . . ? C13 O3 C15 121.59(16) . . ? C20 O5 C21' 128.0(11) . . ? C20 O5 C21 113.1(3) . . ? C21' O5 C21 19.1(8) . . ? 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 C19 H19 O4 0.93 2.49 3.249(3) 139.3 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.295 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.061