# 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_p21n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 Br O4' _chemical_formula_weight 357.24 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 8.3184(19) _cell_length_b 10.279(2) _cell_length_c 19.396(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.917(2) _cell_angle_gamma 90.00 _cell_volume 1633.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2289 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 20.82 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5705 _exptl_absorpt_correction_T_max 0.7861 _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_reflns_number 11523 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3031 _reflns_number_gt 1906 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0375P)^2^+1.4220P] 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 0.0003(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3031 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 -0.37457(6) 0.37505(5) 0.05621(3) 0.0681(2) Uani 1 1 d . . . O4 O -0.0938(3) 0.1544(2) 0.07749(12) 0.0361(6) Uani 1 1 d . . . O3 O -0.1779(3) 0.0702(3) 0.17737(13) 0.0483(7) Uani 1 1 d . . . O1 O 0.4743(3) -0.2355(2) 0.20562(13) 0.0444(7) Uani 1 1 d . . . O2 O 0.4969(3) -0.0287(3) 0.28063(14) 0.0525(7) Uani 1 1 d . . . C5 C 0.3718(4) -0.1369(3) 0.17921(19) 0.0347(9) Uani 1 1 d . . . C6 C 0.3831(4) -0.0248(3) 0.22074(18) 0.0341(9) Uani 1 1 d . . . C7 C -0.2900(5) 0.2674(4) 0.1363(2) 0.0463(10) Uani 1 1 d . . . H7A H -0.2030 0.3136 0.1661 0.056 Uiso 1 1 calc R . . H7B H -0.3761 0.2511 0.1631 0.056 Uiso 1 1 calc R . . C8 C 0.1636(4) -0.0324(4) 0.0972(2) 0.0386(9) Uani 1 1 d . . . H8 H 0.0917 -0.0346 0.0548 0.046 Uiso 1 1 calc R . . C9 C 0.2816(4) 0.0790(4) 0.20013(19) 0.0360(9) Uani 1 1 d . . . H9 H 0.2887 0.1530 0.2281 0.043 Uiso 1 1 calc R . . C10 C 0.2636(4) -0.1390(4) 0.11724(19) 0.0386(9) Uani 1 1 d . . . H10 H 0.2572 -0.2119 0.0886 0.046 Uiso 1 1 calc R . . C11 C 0.1690(4) 0.0754(4) 0.13847(19) 0.0341(8) Uani 1 1 d . . . C12 C -0.2249(4) 0.1380(3) 0.11446(19) 0.0365(9) Uani 1 1 d . . . C13 C 0.1419(5) 0.2893(4) 0.0783(3) 0.0580(12) Uani 1 1 d . . . H13 H 0.2476 0.3127 0.0984 0.070 Uiso 1 1 calc R . . C14 C 0.0598(4) 0.1922(3) 0.1189(2) 0.0365(9) Uani 1 1 d . . . H14 H 0.0387 0.2338 0.1619 0.044 Uiso 1 1 calc R . . C15 C 0.4708(5) -0.3516(4) 0.1653(2) 0.0537(11) Uani 1 1 d . . . H15A H 0.3630 -0.3881 0.1585 0.081 Uiso 1 1 calc R . . H15B H 0.5472 -0.4131 0.1895 0.081 Uiso 1 1 calc R . . H15C H 0.4997 -0.3318 0.1206 0.081 Uiso 1 1 calc R . . C16 C -0.3486(5) 0.0527(4) 0.0696(2) 0.0477(11) Uani 1 1 d . . . H16A H -0.3534 0.0708 0.0202 0.057 Uiso 1 1 calc R . . H16B H -0.4565 0.0632 0.0814 0.057 Uiso 1 1 calc R . . C17 C -0.2803(6) -0.0820(4) 0.0887(3) 0.0629(13) Uani 1 1 d . . . H17A H -0.3668 -0.1463 0.0843 0.075 Uiso 1 1 calc R . . H17B H -0.2025 -0.1072 0.0592 0.075 Uiso 1 1 calc R . . C18 C -0.1979(5) -0.0674(4) 0.1640(3) 0.0588(12) Uani 1 1 d . . . H18A H -0.2645 -0.1058 0.1951 0.071 Uiso 1 1 calc R . . H18B H -0.0926 -0.1105 0.1715 0.071 Uiso 1 1 calc R . . C20 C 0.5346(6) 0.0878(5) 0.3184(2) 0.0709(15) Uani 1 1 d . . . H20A H 0.5636 0.1536 0.2877 0.106 Uiso 1 1 calc R . . H20B H 0.6245 0.0731 0.3558 0.106 Uiso 1 1 calc R . . H20C H 0.4412 0.1159 0.3375 0.106 Uiso 1 1 calc R . . C19 C 0.0878(8) 0.3421(6) 0.0217(4) 0.102(2) Uani 1 1 d . . . H19A H -0.0171 0.3229 -0.0013 0.122 Uiso 1 1 calc R . . H19B H 0.1521 0.4009 0.0021 0.122 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 Br1 0.0694(3) 0.0518(3) 0.0780(4) 0.0090(3) -0.0020(2) 0.0191(2) O4 0.0338(13) 0.0401(15) 0.0323(14) -0.0023(12) 0.0002(11) 0.0003(11) O3 0.0638(17) 0.0447(17) 0.0345(17) 0.0081(14) 0.0031(13) -0.0048(14) O1 0.0574(16) 0.0310(15) 0.0420(17) -0.0015(13) 0.0003(13) 0.0082(13) O2 0.0643(18) 0.0446(17) 0.0404(17) -0.0080(14) -0.0136(14) 0.0107(14) C5 0.0370(19) 0.033(2) 0.035(2) 0.0020(18) 0.0087(17) -0.0007(17) C6 0.039(2) 0.036(2) 0.025(2) 0.0022(17) 0.0003(16) 0.0014(17) C7 0.044(2) 0.046(2) 0.048(3) -0.005(2) 0.0046(19) 0.0036(19) C8 0.039(2) 0.042(2) 0.031(2) -0.0027(19) -0.0028(17) 0.0020(17) C9 0.040(2) 0.034(2) 0.033(2) -0.0057(17) 0.0035(17) -0.0009(16) C10 0.043(2) 0.038(2) 0.034(2) -0.0079(19) 0.0060(17) -0.0028(18) C11 0.0342(19) 0.036(2) 0.031(2) 0.0006(18) 0.0032(16) -0.0024(16) C12 0.0379(19) 0.037(2) 0.033(2) -0.0005(19) 0.0023(17) -0.0017(17) C13 0.059(3) 0.047(3) 0.066(3) 0.018(2) 0.004(2) 0.002(2) C14 0.0346(19) 0.036(2) 0.036(2) 0.0003(18) -0.0005(17) -0.0007(16) C15 0.067(3) 0.040(3) 0.056(3) -0.003(2) 0.012(2) 0.011(2) C16 0.049(2) 0.046(3) 0.047(3) -0.007(2) 0.006(2) -0.0133(19) C17 0.068(3) 0.041(3) 0.082(4) -0.011(3) 0.020(3) -0.016(2) C18 0.059(3) 0.045(3) 0.074(4) 0.016(2) 0.016(2) -0.004(2) C20 0.076(3) 0.065(3) 0.060(3) -0.022(3) -0.021(2) 0.014(3) C19 0.099(4) 0.094(5) 0.113(5) 0.029(4) 0.018(4) -0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.938(4) . ? O4 C12 1.415(4) . ? O4 C14 1.440(4) . ? O3 C12 1.401(4) . ? O3 C18 1.442(5) . ? O1 C5 1.366(4) . ? O1 C15 1.424(4) . ? O2 C6 1.367(4) . ? O2 C20 1.411(5) . ? C5 C10 1.372(5) . ? C5 C6 1.400(5) . ? C6 C9 1.376(5) . ? C7 C12 1.523(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C11 1.363(5) . ? C8 C10 1.390(5) . ? C8 H8 0.9300 . ? C9 C11 1.387(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C14 1.514(5) . ? C12 C16 1.509(5) . ? C13 C19 1.238(7) . ? C13 C14 1.506(5) . ? C13 H13 0.9300 . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.518(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.510(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C19 H19A 0.9300 . ? C19 H19B 0.9300 . ? 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 C12 O4 C14 115.9(3) . . ? C12 O3 C18 109.0(3) . . ? C5 O1 C15 117.6(3) . . ? C6 O2 C20 118.4(3) . . ? O1 C5 C10 126.1(3) . . ? O1 C5 C6 114.8(3) . . ? C10 C5 C6 119.1(3) . . ? O2 C6 C9 124.8(3) . . ? O2 C6 C5 115.6(3) . . ? C9 C6 C5 119.6(3) . . ? C12 C7 Br1 111.9(3) . . ? C12 C7 H7A 109.2 . . ? Br1 C7 H7A 109.2 . . ? C12 C7 H7B 109.2 . . ? Br1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C11 C8 C10 121.2(3) . . ? C11 C8 H8 119.4 . . ? C10 C8 H8 119.4 . . ? C6 C9 C11 121.3(3) . . ? C6 C9 H9 119.4 . . ? C11 C9 H9 119.4 . . ? C5 C10 C8 120.3(3) . . ? C5 C10 H10 119.9 . . ? C8 C10 H10 119.9 . . ? C8 C11 C9 118.5(3) . . ? C8 C11 C14 122.6(3) . . ? C9 C11 C14 118.8(3) . . ? O3 C12 O4 112.2(3) . . ? O3 C12 C16 105.9(3) . . ? O4 C12 C16 106.6(3) . . ? O3 C12 C7 104.6(3) . . ? O4 C12 C7 112.2(3) . . ? C16 C12 C7 115.3(3) . . ? C19 C13 C14 128.8(5) . . ? C19 C13 H13 115.6 . . ? C14 C13 H13 115.6 . . ? O4 C14 C13 109.0(3) . . ? O4 C14 C11 111.2(3) . . ? C13 C14 C11 110.5(3) . . ? O4 C14 H14 108.7 . . ? C13 C14 H14 108.7 . . ? C11 C14 H14 108.7 . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 101.5(3) . . ? C12 C16 H16A 111.5 . . ? C17 C16 H16A 111.5 . . ? C12 C16 H16B 111.5 . . ? C17 C16 H16B 111.5 . . ? H16A C16 H16B 109.3 . . ? C18 C17 C16 103.5(3) . . ? C18 C17 H17A 111.1 . . ? C16 C17 H17A 111.1 . . ? C18 C17 H17B 111.1 . . ? C16 C17 H17B 111.1 . . ? H17A C17 H17B 109.0 . . ? O3 C18 C17 106.9(3) . . ? O3 C18 H18A 110.3 . . ? C17 C18 H18A 110.3 . . ? O3 C18 H18B 110.3 . . ? C17 C18 H18B 110.3 . . ? H18A C18 H18B 108.6 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C19 H19A 120.0 . . ? C13 C19 H19B 120.0 . . ? H19A C19 H19B 120.0 . . ? 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 C15 O1 C5 C10 0.5(5) . . . . ? C15 O1 C5 C6 -179.0(3) . . . . ? C20 O2 C6 C9 -11.5(5) . . . . ? C20 O2 C6 C5 169.1(4) . . . . ? O1 C5 C6 O2 1.4(4) . . . . ? C10 C5 C6 O2 -178.1(3) . . . . ? O1 C5 C6 C9 -178.0(3) . . . . ? C10 C5 C6 C9 2.5(5) . . . . ? O2 C6 C9 C11 -180.0(3) . . . . ? C5 C6 C9 C11 -0.6(5) . . . . ? O1 C5 C10 C8 178.7(3) . . . . ? C6 C5 C10 C8 -1.8(5) . . . . ? C11 C8 C10 C5 -0.7(5) . . . . ? C10 C8 C11 C9 2.6(5) . . . . ? C10 C8 C11 C14 -178.9(3) . . . . ? C6 C9 C11 C8 -1.9(5) . . . . ? C6 C9 C11 C14 179.5(3) . . . . ? C18 O3 C12 O4 -88.6(3) . . . . ? C18 O3 C12 C16 27.3(4) . . . . ? C18 O3 C12 C7 149.5(3) . . . . ? C14 O4 C12 O3 -43.6(4) . . . . ? C14 O4 C12 C16 -159.0(3) . . . . ? C14 O4 C12 C7 73.8(4) . . . . ? Br1 C7 C12 O3 -176.7(2) . . . . ? Br1 C7 C12 O4 61.4(3) . . . . ? Br1 C7 C12 C16 -60.9(4) . . . . ? C12 O4 C14 C13 -141.0(3) . . . . ? C12 O4 C14 C11 96.9(3) . . . . ? C19 C13 C14 O4 6.7(7) . . . . ? C19 C13 C14 C11 129.2(6) . . . . ? C8 C11 C14 O4 30.2(5) . . . . ? C9 C11 C14 O4 -151.2(3) . . . . ? C8 C11 C14 C13 -91.0(4) . . . . ? C9 C11 C14 C13 87.5(4) . . . . ? O3 C12 C16 C17 -36.5(4) . . . . ? O4 C12 C16 C17 83.1(4) . . . . ? C7 C12 C16 C17 -151.6(3) . . . . ? C12 C16 C17 C18 31.4(4) . . . . ? C12 O3 C18 C17 -6.5(4) . . . . ? C16 C17 C18 O3 -16.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.547 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 962589' ####################################################################### # # 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_p-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 O5' _chemical_formula_weight 384.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.143(14) _cell_length_b 8.81(2) _cell_length_c 19.64(4) _cell_angle_alpha 83.80(2) _cell_angle_beta 83.37(2) _cell_angle_gamma 76.77(2) _cell_volume 1024(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1162 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 21.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details SADABS _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_reflns_number 5691 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.2295 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3531 _reflns_number_gt 1921 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3531 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1544 _refine_ls_R_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.3259 _refine_ls_wR_factor_gt 0.2607 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 O5 O 1.2545(8) 0.2721(6) 0.0105(2) 0.1026(15) Uani 1 1 d . . . C23 C 1.4808(14) 0.2280(11) -0.0123(4) 0.123(3) Uani 1 1 d . . . H23A H 1.5550 0.3097 -0.0062 0.184 Uiso 1 1 calc R . . H23B H 1.4960 0.2101 -0.0601 0.184 Uiso 1 1 calc R . . H23C H 1.5478 0.1336 0.0137 0.184 Uiso 1 1 calc R . . C1 C 1.1408(9) 0.2622(7) 0.4990(3) 0.0763(18) Uani 1 1 d . . . H1A H 1.2402 0.3222 0.5127 0.092 Uiso 1 1 calc R . . H1B H 1.2259 0.1569 0.4922 0.092 Uiso 1 1 calc R . . C2 C 0.9496(9) 0.2590(7) 0.5518(3) 0.0761(17) Uani 1 1 d . . . H2A H 0.9206 0.3496 0.5782 0.091 Uiso 1 1 calc R . . H2B H 0.9797 0.1650 0.5830 0.091 Uiso 1 1 calc R . . C3 C 0.7539(9) 0.2612(7) 0.5124(3) 0.0754(17) Uani 1 1 d . . . H3A H 0.6284 0.3456 0.5250 0.091 Uiso 1 1 calc R . . H3B H 0.7059 0.1629 0.5212 0.091 Uiso 1 1 calc R . . C4 C 0.8402(8) 0.2867(6) 0.4367(3) 0.0572(14) Uani 1 1 d . . . C5 C 0.6970(8) 0.4021(5) 0.3890(3) 0.0581(14) Uani 1 1 d . . . H5A H 0.7115 0.5080 0.3932 0.070 Uiso 1 1 calc R . . H5B H 0.5402 0.3972 0.3985 0.070 Uiso 1 1 calc R . . C6 C 0.7894(8) 0.3505(4) 0.3180(3) 0.0494(12) Uani 1 1 d . . . H6 H 0.6647 0.3635 0.2894 0.059 Uiso 1 1 calc R . . C7 C 0.8910(8) 0.1727(5) 0.3330(3) 0.0499(13) Uani 1 1 d . . . H7 H 1.0497 0.1507 0.3151 0.060 Uiso 1 1 calc R . . C8 C 0.7750(7) 0.0656(5) 0.3037(3) 0.0465(12) Uani 1 1 d . . . C9 C 0.8366(7) 0.0305(5) 0.2358(3) 0.0500(13) Uani 1 1 d . . . H9 H 0.9496 0.0718 0.2100 0.060 Uiso 1 1 calc R . . C10 C 0.7318(8) -0.0646(5) 0.2066(3) 0.0513(12) Uani 1 1 d . . . C11 C 0.5599(8) -0.1264(5) 0.2439(3) 0.0505(13) Uani 1 1 d . . . C12 C 0.4990(8) -0.0903(5) 0.3111(3) 0.0565(14) Uani 1 1 d . . . H12 H 0.3842 -0.1298 0.3368 0.068 Uiso 1 1 calc R . . C13 C 0.6070(8) 0.0039(5) 0.3406(3) 0.0538(13) Uani 1 1 d . . . H13 H 0.5653 0.0259 0.3861 0.065 Uiso 1 1 calc R . . C14 C 0.9695(11) -0.0647(8) 0.1017(3) 0.0885(19) Uani 1 1 d . . . H14A H 0.9452 0.0471 0.0942 0.133 Uiso 1 1 calc R . . H14B H 0.9931 -0.1090 0.0582 0.133 Uiso 1 1 calc R . . H14C H 1.0994 -0.1043 0.1265 0.133 Uiso 1 1 calc R . . C15 C 0.3157(8) -0.3017(5) 0.2487(3) 0.0703(17) Uani 1 1 d . . . H15A H 0.3887 -0.3654 0.2859 0.105 Uiso 1 1 calc R . . H15B H 0.2694 -0.3671 0.2197 0.105 Uiso 1 1 calc R . . H15C H 0.1865 -0.2287 0.2669 0.105 Uiso 1 1 calc R . . C16 C 0.9613(9) 0.4405(5) 0.2818(3) 0.0637(15) Uani 1 1 d . . . H16A H 0.8927 0.5514 0.2791 0.076 Uiso 1 1 calc R . . H16B H 1.0869 0.4236 0.3095 0.076 Uiso 1 1 calc R . . C17 C 1.0498(9) 0.3944(5) 0.2100(3) 0.0567(14) Uani 1 1 d . . . C18 C 0.9151(10) 0.4424(6) 0.1568(3) 0.0764(18) Uani 1 1 d . . . H18 H 0.7728 0.5055 0.1654 0.092 Uiso 1 1 calc R . . C19 C 0.9871(11) 0.3988(7) 0.0906(4) 0.087(2) Uani 1 1 d . . . H19 H 0.8923 0.4288 0.0556 0.104 Uiso 1 1 calc R . . C20 C 1.1987(10) 0.3114(6) 0.0779(3) 0.0713(16) Uani 1 1 d . . . C21 C 1.3363(9) 0.2629(6) 0.1295(3) 0.0678(16) Uani 1 1 d . . . H21 H 1.4799 0.2021 0.1206 0.081 Uiso 1 1 calc R . . C22 C 1.2591(9) 0.3056(6) 0.1957(3) 0.0646(15) Uani 1 1 d . . . H22 H 1.3527 0.2726 0.2309 0.078 Uiso 1 1 calc R . . O1 O 0.8761(6) 0.1448(3) 0.40686(18) 0.0638(11) Uani 1 1 d . . . O2 O 1.0459(5) 0.3341(4) 0.43734(18) 0.0642(10) Uani 1 1 d . . . O3 O 0.7805(6) -0.1057(4) 0.1400(2) 0.0763(12) Uani 1 1 d . . . O4 O 0.4663(6) -0.2191(4) 0.20996(19) 0.0707(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.086(3) 0.137(4) 0.076(3) -0.006(3) -0.008(3) -0.007(3) C23 0.092(6) 0.164(8) 0.107(6) -0.032(5) 0.007(5) -0.016(5) C1 0.055(3) 0.084(4) 0.099(5) -0.004(3) -0.029(3) -0.024(3) C2 0.062(4) 0.087(4) 0.079(5) 0.007(3) -0.011(3) -0.020(3) C3 0.059(3) 0.093(4) 0.080(5) -0.003(3) -0.002(3) -0.032(3) C4 0.038(3) 0.063(3) 0.077(4) -0.003(3) -0.006(2) -0.026(2) C5 0.055(3) 0.056(3) 0.066(4) -0.012(2) -0.007(3) -0.014(2) C6 0.048(3) 0.040(2) 0.064(3) -0.006(2) -0.007(2) -0.015(2) C7 0.046(3) 0.044(2) 0.062(4) 0.003(2) -0.010(2) -0.017(2) C8 0.044(3) 0.039(2) 0.059(3) 0.002(2) -0.010(2) -0.0134(19) C9 0.043(3) 0.043(2) 0.067(4) -0.002(2) -0.003(2) -0.019(2) C10 0.057(3) 0.043(2) 0.056(3) -0.008(2) -0.003(2) -0.015(2) C11 0.052(3) 0.036(2) 0.071(4) -0.007(2) -0.010(3) -0.021(2) C12 0.049(3) 0.053(3) 0.073(4) -0.001(3) 0.000(3) -0.026(2) C13 0.054(3) 0.053(3) 0.056(3) 0.001(2) -0.002(2) -0.020(2) C14 0.084(4) 0.122(5) 0.070(4) -0.012(4) 0.009(3) -0.050(4) C15 0.058(3) 0.052(3) 0.111(5) -0.010(3) -0.005(3) -0.031(2) C16 0.073(4) 0.046(3) 0.080(4) -0.003(3) -0.009(3) -0.028(2) C17 0.060(3) 0.041(2) 0.073(4) 0.007(2) -0.008(3) -0.024(2) C18 0.069(4) 0.071(3) 0.077(5) 0.011(3) -0.003(3) 0.001(3) C19 0.073(4) 0.097(4) 0.077(5) 0.018(4) -0.015(4) 0.001(3) C20 0.070(4) 0.073(4) 0.067(4) -0.001(3) -0.008(3) -0.009(3) C21 0.050(3) 0.071(3) 0.079(5) -0.005(3) -0.008(3) -0.007(3) C22 0.054(3) 0.064(3) 0.079(4) -0.001(3) -0.017(3) -0.018(3) O1 0.082(3) 0.0476(19) 0.071(3) 0.0061(17) -0.028(2) -0.0269(17) O2 0.052(2) 0.076(2) 0.075(3) -0.0103(18) -0.0099(18) -0.0322(17) O3 0.078(3) 0.084(3) 0.080(3) -0.028(2) 0.009(2) -0.041(2) O4 0.071(2) 0.064(2) 0.089(3) -0.0177(18) -0.003(2) -0.0366(18) _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 O5 C23 1.390(9) . ? O5 C20 1.390(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C1 O2 1.426(6) . ? C1 C2 1.479(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.499(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.530(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O1 1.399(6) . ? C4 O2 1.420(6) . ? C4 C5 1.503(7) . ? C5 C6 1.520(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C16 1.529(7) . ? C6 C7 1.557(6) . ? C6 H6 0.9800 . ? C7 O1 1.440(6) . ? C7 C8 1.501(6) . ? C7 H7 0.9800 . ? C8 C13 1.373(6) . ? C8 C9 1.391(7) . ? C9 C10 1.371(7) . ? C9 H9 0.9300 . ? C10 O3 1.376(6) . ? C10 C11 1.394(7) . ? C11 O4 1.365(6) . ? C11 C12 1.381(7) . ? C12 C13 1.382(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O3 1.406(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O4 1.411(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.515(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C22 1.359(7) . ? C17 C18 1.377(8) . ? C18 C19 1.389(9) . ? C18 H18 0.9300 . ? C19 C20 1.361(8) . ? C19 H19 0.9300 . ? C20 C21 1.365(8) . ? C21 C22 1.391(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 C23 O5 C20 118.0(5) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O2 C1 C2 106.2(5) . . ? O2 C1 H1A 110.5 . . ? C2 C1 H1A 110.5 . . ? O2 C1 H1B 110.5 . . ? C2 C1 H1B 110.5 . . ? H1A C1 H1B 108.7 . . ? C1 C2 C3 105.0(5) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C2 C3 C4 105.1(5) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? O1 C4 O2 110.8(4) . . ? O1 C4 C5 104.2(4) . . ? O2 C4 C5 108.2(4) . . ? O1 C4 C3 108.5(4) . . ? O2 C4 C3 105.4(4) . . ? C5 C4 C3 119.7(5) . . ? C4 C5 C6 103.7(4) . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C6 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C5 C6 C16 113.4(4) . . ? C5 C6 C7 102.8(4) . . ? C16 C6 C7 112.9(4) . . ? C5 C6 H6 109.2 . . ? C16 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? O1 C7 C8 109.6(3) . . ? O1 C7 C6 105.6(4) . . ? C8 C7 C6 114.9(4) . . ? O1 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C13 C8 C9 118.7(4) . . ? C13 C8 C7 122.6(5) . . ? C9 C8 C7 118.6(4) . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 O3 124.7(4) . . ? C9 C10 C11 120.9(5) . . ? O3 C10 C11 114.4(4) . . ? O4 C11 C12 125.5(4) . . ? O4 C11 C10 116.2(5) . . ? C12 C11 C10 118.3(4) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C8 C13 C12 121.0(5) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C6 114.2(4) . . ? C17 C16 H16A 108.7 . . ? C6 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C6 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C22 C17 C18 118.1(6) . . ? C22 C17 C16 122.3(5) . . ? C18 C17 C16 119.6(5) . . ? C17 C18 C19 121.4(6) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C20 C19 C18 118.9(6) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C19 C20 C21 120.9(6) . . ? C19 C20 O5 114.7(6) . . ? C21 C20 O5 124.4(6) . . ? C20 C21 C22 119.2(6) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C17 C22 C21 121.4(5) . . ? C17 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C4 O1 C7 109.9(3) . . ? C4 O2 C1 107.0(4) . . ? C10 O3 C14 117.9(4) . . ? C11 O4 C15 117.7(4) . . ? 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 O2 C1 C2 C3 25.3(6) . . . . ? C1 C2 C3 C4 -7.0(6) . . . . ? C2 C3 C4 O1 105.1(5) . . . . ? C2 C3 C4 O2 -13.6(6) . . . . ? C2 C3 C4 C5 -135.6(5) . . . . ? O1 C4 C5 C6 -37.4(4) . . . . ? O2 C4 C5 C6 80.6(5) . . . . ? C3 C4 C5 C6 -158.8(4) . . . . ? C4 C5 C6 C16 -95.9(5) . . . . ? C4 C5 C6 C7 26.3(4) . . . . ? C5 C6 C7 O1 -7.1(4) . . . . ? C16 C6 C7 O1 115.5(4) . . . . ? C5 C6 C7 C8 113.8(5) . . . . ? C16 C6 C7 C8 -123.6(5) . . . . ? O1 C7 C8 C13 25.0(6) . . . . ? C6 C7 C8 C13 -93.7(5) . . . . ? O1 C7 C8 C9 -156.5(4) . . . . ? C6 C7 C8 C9 84.7(5) . . . . ? C13 C8 C9 C10 -0.3(6) . . . . ? C7 C8 C9 C10 -178.8(4) . . . . ? C8 C9 C10 O3 179.9(4) . . . . ? C8 C9 C10 C11 0.9(7) . . . . ? C9 C10 C11 O4 179.7(4) . . . . ? O3 C10 C11 O4 0.7(6) . . . . ? C9 C10 C11 C12 -0.5(7) . . . . ? O3 C10 C11 C12 -179.6(4) . . . . ? O4 C11 C12 C13 179.4(4) . . . . ? C10 C11 C12 C13 -0.3(7) . . . . ? C9 C8 C13 C12 -0.6(6) . . . . ? C7 C8 C13 C12 177.9(4) . . . . ? C11 C12 C13 C8 0.9(7) . . . . ? C5 C6 C16 C17 -178.1(4) . . . . ? C7 C6 C16 C17 65.4(6) . . . . ? C6 C16 C17 C22 -105.3(5) . . . . ? C6 C16 C17 C18 74.3(6) . . . . ? C22 C17 C18 C19 1.6(8) . . . . ? C16 C17 C18 C19 -178.0(5) . . . . ? C17 C18 C19 C20 -2.4(9) . . . . ? C18 C19 C20 C21 2.0(9) . . . . ? C18 C19 C20 O5 179.3(5) . . . . ? C23 O5 C20 C19 160.1(7) . . . . ? C23 O5 C20 C21 -22.7(9) . . . . ? C19 C20 C21 C22 -0.8(8) . . . . ? O5 C20 C21 C22 -177.9(5) . . . . ? C18 C17 C22 C21 -0.4(7) . . . . ? C16 C17 C22 C21 179.2(4) . . . . ? C20 C21 C22 C17 0.0(7) . . . . ? O2 C4 O1 C7 -82.0(4) . . . . ? C5 C4 O1 C7 34.1(5) . . . . ? C3 C4 O1 C7 162.7(4) . . . . ? C8 C7 O1 C4 -141.2(4) . . . . ? C6 C7 O1 C4 -16.8(4) . . . . ? O1 C4 O2 C1 -87.2(5) . . . . ? C5 C4 O2 C1 159.2(4) . . . . ? C3 C4 O2 C1 30.0(5) . . . . ? C2 C1 O2 C4 -35.2(6) . . . . ? C9 C10 O3 C14 8.7(7) . . . . ? C11 C10 O3 C14 -172.3(4) . . . . ? C12 C11 O4 C15 -8.7(7) . . . . ? C10 C11 O4 C15 170.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.272 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 962591' ####################################################################### # # 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_p-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 O5 S' _chemical_formula_weight 388.46 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.215(18) _cell_length_b 9.284(15) _cell_length_c 19.41(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.341(19) _cell_angle_gamma 90.00 _cell_volume 2021(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7900 _diffrn_reflns_av_R_equivalents 0.1347 _diffrn_reflns_av_sigmaI/netI 0.1484 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3511 _reflns_number_gt 1311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3511 _refine_ls_number_parameters 245 _refine_ls_number_restraints 114 _refine_ls_R_factor_all 0.2024 _refine_ls_R_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.3007 _refine_ls_wR_factor_gt 0.2647 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.147 _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 0.4413(9) 1.1297(11) -0.0790(4) 0.130(3) Uani 1 1 d . . . H1A H 0.4193 1.0309 -0.0719 0.196 Uiso 1 1 calc R . . H1B H 0.5260 1.1362 -0.0850 0.196 Uiso 1 1 calc R . . H1C H 0.4016 1.1659 -0.1194 0.196 Uiso 1 1 calc R . . C2 C 0.4049(8) 1.2182(9) -0.0170(4) 0.087(2) Uani 1 1 d . . . C3 C 0.2875(8) 1.2210(10) 0.0066(4) 0.097(3) Uani 1 1 d . . . H3 H 0.2297 1.1677 -0.0166 0.116 Uiso 1 1 calc R . . C4 C 0.2550(6) 1.3015(9) 0.0638(5) 0.088(2) Uani 1 1 d . . . H4 H 0.1763 1.3025 0.0786 0.105 Uiso 1 1 calc R . . C5 C 0.3413(6) 1.3804(7) 0.0986(3) 0.0645(18) Uani 1 1 d . . . C6 C 0.4559(7) 1.3789(10) 0.0770(5) 0.103(3) Uani 1 1 d . . . H6 H 0.5134 1.4319 0.1006 0.123 Uiso 1 1 calc R . . C7 C 0.4874(8) 1.2993(12) 0.0202(5) 0.115(3) Uani 1 1 d . . . H7 H 0.5665 1.2998 0.0061 0.138 Uiso 1 1 calc R . . C8 C 0.3024(6) 1.2488(8) 0.2449(3) 0.0624(18) Uani 1 1 d . . . C9 C 0.3715(6) 1.1311(9) 0.2307(4) 0.077(2) Uani 1 1 d . . . H9 H 0.4470 1.1416 0.2118 0.093 Uiso 1 1 calc R . . C10 C 0.3266(7) 0.9977(9) 0.2451(3) 0.078(2) Uani 1 1 d . . . H10 H 0.3746 0.9180 0.2367 0.094 Uiso 1 1 calc R . . C11 C 0.2149(7) 0.9748(8) 0.2711(3) 0.0710(19) Uani 1 1 d . . . C12 C 0.1475(7) 1.0967(10) 0.2837(4) 0.085(2) Uani 1 1 d . . . H12 H 0.0707 1.0853 0.3007 0.102 Uiso 1 1 calc R . . C13 C 0.1883(7) 1.2320(9) 0.2725(4) 0.082(2) Uani 1 1 d . . . H13 H 0.1415 1.3118 0.2828 0.098 Uiso 1 1 calc R . . C14 C 0.1698(7) 0.8278(8) 0.2849(4) 0.095(3) Uani 1 1 d . . . H14A H 0.1084 0.8067 0.2510 0.114 Uiso 1 1 calc R . . H14B H 0.2347 0.7607 0.2771 0.114 Uiso 1 1 calc R . . C15 C 0.1223(11) 0.7992(10) 0.3508(5) 0.143(4) Uani 1 1 d . . . H15 H 0.0474 0.8536 0.3503 0.172 Uiso 1 1 calc R . . C16 C 0.0813(9) 0.6478(10) 0.3670(5) 0.131(2) Uani 1 1 d U . . H16A H 0.0134 0.6217 0.3384 0.158 Uiso 1 1 calc R . . H16B H 0.1450 0.5792 0.3591 0.158 Uiso 1 1 calc R . . C17 C 0.1764(9) 0.8426(10) 0.4162(4) 0.126(2) Uani 1 1 d U . . H17A H 0.1564 0.9419 0.4264 0.152 Uiso 1 1 calc R . . H17B H 0.2625 0.8343 0.4137 0.152 Uiso 1 1 calc R . . C18 C 0.1292(8) 0.7456(8) 0.4707(3) 0.082(2) Uani 1 1 d . . . C19 C 0.0553(10) 0.8003(12) 0.5249(5) 0.141(2) Uani 1 1 d U . . H19A H -0.0270 0.8067 0.5096 0.169 Uiso 1 1 calc R . . H19B H 0.0818 0.8954 0.5389 0.169 Uiso 1 1 calc R . . C20 C 0.0667(10) 0.6981(11) 0.5825(5) 0.131(2) Uani 1 1 d U . . H20A H 0.0678 0.7488 0.6261 0.157 Uiso 1 1 calc R . . H20B H 0.0005 0.6308 0.5824 0.157 Uiso 1 1 calc R . . C21 C 0.1737(10) 0.6258(12) 0.5725(5) 0.135(2) Uani 1 1 d U . . H21A H 0.1614 0.5224 0.5740 0.162 Uiso 1 1 calc R . . H21B H 0.2311 0.6519 0.6079 0.162 Uiso 1 1 calc R . . O3 O 0.3499(4) 1.3872(5) 0.2344(2) 0.0761(14) Uani 1 1 d . . . O1 O 0.1738(4) 1.4893(5) 0.1755(3) 0.0878(16) Uani 1 1 d . . . O2 O 0.3711(4) 1.6085(5) 0.1753(3) 0.0956(17) Uani 1 1 d . . . O4 O 0.0484(6) 0.6497(7) 0.4392(3) 0.1425(19) Uani 1 1 d U . . O5 O 0.2153(6) 0.6681(7) 0.5066(4) 0.1379(19) Uani 1 1 d U . . S1 S 0.30123(17) 1.4815(2) 0.17112(10) 0.0751(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.160(9) 0.151(9) 0.080(6) -0.010(6) 0.010(6) 0.001(7) C2 0.085(6) 0.102(6) 0.073(5) 0.012(5) 0.004(5) -0.001(5) C3 0.085(7) 0.117(7) 0.088(6) -0.020(6) -0.012(5) -0.019(5) C4 0.053(5) 0.103(6) 0.108(7) 0.000(5) -0.002(5) -0.007(5) C5 0.053(4) 0.069(5) 0.072(5) 0.013(4) -0.005(4) -0.005(4) C6 0.060(6) 0.140(8) 0.108(7) -0.019(6) -0.005(5) -0.023(5) C7 0.072(6) 0.158(9) 0.115(8) -0.012(7) 0.023(6) -0.025(6) C8 0.060(5) 0.069(5) 0.058(4) 0.009(4) -0.012(3) 0.001(4) C9 0.056(5) 0.094(6) 0.082(5) 0.024(5) -0.003(4) 0.005(5) C10 0.089(6) 0.082(6) 0.064(5) 0.014(4) 0.001(4) 0.014(5) C11 0.084(6) 0.078(5) 0.051(4) 0.006(4) 0.003(4) -0.001(5) C12 0.080(6) 0.090(6) 0.085(6) 0.009(5) 0.019(4) -0.009(5) C13 0.074(6) 0.082(6) 0.089(6) 0.010(5) 0.014(4) 0.015(4) C14 0.137(7) 0.090(6) 0.058(5) 0.009(4) 0.006(5) -0.016(5) C15 0.249(12) 0.108(7) 0.072(7) 0.012(5) -0.016(7) -0.075(8) C16 0.173(5) 0.131(5) 0.090(4) 0.026(4) 0.002(4) -0.047(4) C17 0.155(5) 0.133(4) 0.091(4) 0.032(4) 0.005(4) -0.033(4) C18 0.125(7) 0.081(5) 0.040(4) 0.016(4) -0.026(4) -0.038(5) C19 0.165(5) 0.145(5) 0.113(4) 0.035(4) 0.015(4) -0.014(4) C20 0.162(5) 0.132(5) 0.099(4) 0.022(4) 0.030(4) -0.028(4) C21 0.157(5) 0.145(5) 0.104(4) 0.037(4) -0.003(4) -0.021(4) O3 0.072(3) 0.080(3) 0.076(3) 0.008(3) -0.022(2) -0.011(3) O1 0.061(3) 0.099(4) 0.104(4) 0.013(3) -0.004(2) 0.013(3) O2 0.096(4) 0.072(3) 0.118(4) 0.009(3) -0.012(3) -0.020(3) O4 0.179(4) 0.142(4) 0.107(4) 0.035(3) -0.006(3) -0.052(4) O5 0.141(4) 0.157(4) 0.116(4) 0.042(3) 0.012(3) -0.017(3) S1 0.0657(13) 0.0731(13) 0.0864(15) 0.0099(11) -0.0067(9) 0.0008(11) _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 C2 1.516(11) . ? C2 C7 1.391(11) . ? C2 C3 1.396(10) . ? C3 C4 1.390(10) . ? C4 C5 1.386(9) . ? C5 C6 1.354(9) . ? C5 S1 1.752(7) . ? C6 C7 1.376(11) . ? C8 C9 1.369(9) . ? C8 C13 1.399(9) . ? C8 O3 1.406(8) . ? C9 C10 1.365(9) . ? C10 C11 1.370(9) . ? C11 C12 1.384(10) . ? C11 C14 1.481(9) . ? C12 C13 1.355(10) . ? C14 C15 1.415(10) . ? C15 C17 1.459(12) . ? C15 C16 1.513(11) . ? C16 O4 1.451(10) . ? C17 C18 1.490(10) . ? C18 O5 1.388(9) . ? C18 O4 1.408(8) . ? C18 C19 1.436(11) . ? C19 C20 1.472(12) . ? C20 C21 1.390(11) . ? C21 O5 1.418(9) . ? O3 S1 1.602(5) . ? O1 S1 1.433(5) . ? O2 S1 1.418(5) . ? 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 C7 C2 C3 116.5(8) . . ? C7 C2 C1 121.6(9) . . ? C3 C2 C1 121.9(9) . . ? C4 C3 C2 121.6(8) . . ? C5 C4 C3 119.2(7) . . ? C6 C5 C4 120.3(7) . . ? C6 C5 S1 120.2(6) . . ? C4 C5 S1 119.5(6) . . ? C5 C6 C7 120.2(8) . . ? C6 C7 C2 122.2(8) . . ? C9 C8 C13 120.6(7) . . ? C9 C8 O3 119.0(7) . . ? C13 C8 O3 120.4(7) . . ? C10 C9 C8 118.2(7) . . ? C9 C10 C11 123.7(7) . . ? C10 C11 C12 116.1(7) . . ? C10 C11 C14 121.6(7) . . ? C12 C11 C14 122.3(7) . . ? C13 C12 C11 123.0(7) . . ? C12 C13 C8 118.4(7) . . ? C15 C14 C11 117.8(7) . . ? C14 C15 C17 125.3(9) . . ? C14 C15 C16 118.6(8) . . ? C17 C15 C16 101.6(8) . . ? O4 C16 C15 105.6(8) . . ? C15 C17 C18 107.6(7) . . ? O5 C18 O4 109.5(7) . . ? O5 C18 C19 102.6(7) . . ? O4 C18 C19 99.7(8) . . ? O5 C18 C17 114.9(8) . . ? O4 C18 C17 107.7(6) . . ? C19 C18 C17 121.1(8) . . ? C18 C19 C20 106.3(9) . . ? C21 C20 C19 106.0(8) . . ? C20 C21 O5 106.3(8) . . ? C8 O3 S1 118.8(4) . . ? C18 O4 C16 105.1(6) . . ? C18 O5 C21 111.4(7) . . ? O2 S1 O1 120.4(3) . . ? O2 S1 O3 103.0(3) . . ? O1 S1 O3 108.5(3) . . ? O2 S1 C5 110.3(3) . . ? O1 S1 C5 109.6(3) . . ? O3 S1 C5 103.6(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.022 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 962592' ####################################################################### # # 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_p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 O5 S' _chemical_formula_weight 388.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.137(11) _cell_length_b 9.246(9) _cell_length_c 18.976(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.813(11) _cell_angle_gamma 90.00 _cell_volume 1954(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1832 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 20.75 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9529 _exptl_absorpt_correction_T_max 0.9584 _exptl_absorpt_process_details SADABS _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_reflns_number 13647 _diffrn_reflns_av_R_equivalents 0.0931 _diffrn_reflns_av_sigmaI/netI 0.0894 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3616 _reflns_number_gt 1695 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.3000P)^2^+0.2990P] 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 3616 _refine_ls_number_parameters 245 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.2005 _refine_ls_R_factor_gt 0.1190 _refine_ls_wR_factor_ref 0.4400 _refine_ls_wR_factor_gt 0.3704 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 1.005 _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 0.1915(13) 0.1338(14) 0.5723(6) 0.131(3) Uani 1 1 d U . . H1A H 0.2491 0.1593 0.6091 0.157 Uiso 1 1 calc R . . H1B H 0.1872 0.0292 0.5692 0.157 Uiso 1 1 calc R . . C2 C 0.0792(13) 0.1909(15) 0.5876(6) 0.128(3) Uani 1 1 d U . . H2A H 0.0816 0.2413 0.6324 0.154 Uiso 1 1 calc R . . H2B H 0.0196 0.1146 0.5898 0.154 Uiso 1 1 calc R . . C3 C 0.0500(12) 0.2930(15) 0.5291(6) 0.125(3) Uani 1 1 d U . . H3A H -0.0335 0.2852 0.5143 0.150 Uiso 1 1 calc R . . H3B H 0.0672 0.3922 0.5424 0.150 Uiso 1 1 calc R . . C4 C 0.1315(11) 0.2422(12) 0.4733(5) 0.102(2) Uani 1 1 d U . . C5 C 0.1688(11) 0.3521(11) 0.4183(5) 0.106(3) Uani 1 1 d U . . H5A H 0.1060 0.4234 0.4108 0.127 Uiso 1 1 calc R . . H5B H 0.2418 0.4014 0.4331 0.127 Uiso 1 1 calc R . . C6 C 0.1882(13) 0.2701(11) 0.3553(5) 0.111(3) Uani 1 1 d U . . H6 H 0.2738 0.2463 0.3532 0.134 Uiso 1 1 calc R . . C7 C 0.1196(13) 0.1316(12) 0.3695(6) 0.124(3) Uani 1 1 d U . . H7A H 0.0566 0.1189 0.3342 0.149 Uiso 1 1 calc R . . H7B H 0.1734 0.0493 0.3671 0.149 Uiso 1 1 calc R . . C8 C 0.1525(9) 0.3341(9) 0.2880(4) 0.084(2) Uani 1 1 d . . . H8A H 0.0656 0.3425 0.2866 0.101 Uiso 1 1 calc R . . H8B H 0.1752 0.2686 0.2506 0.101 Uiso 1 1 calc R . . C9 C 0.2047(7) 0.4786(8) 0.2732(4) 0.0663(19) Uani 1 1 d . . . C10 C 0.1388(8) 0.6012(10) 0.2860(5) 0.079(2) Uani 1 1 d . . . H10 H 0.0614 0.5920 0.3031 0.095 Uiso 1 1 calc R . . C11 C 0.1828(8) 0.7325(9) 0.2744(4) 0.077(2) Uani 1 1 d . . . H11 H 0.1366 0.8142 0.2831 0.093 Uiso 1 1 calc R . . C12 C 0.2953(7) 0.7457(8) 0.2498(4) 0.0649(19) Uani 1 1 d . . . C13 C 0.3626(7) 0.6291(10) 0.2354(4) 0.077(2) Uani 1 1 d . . . H13 H 0.4394 0.6399 0.2175 0.093 Uiso 1 1 calc R . . C14 C 0.3165(8) 0.4943(9) 0.2474(4) 0.077(2) Uani 1 1 d . . . H14 H 0.3624 0.4129 0.2377 0.092 Uiso 1 1 calc R . . C15 C 0.3384(7) 0.8839(8) 0.1026(4) 0.074(2) Uani 1 1 d . . . C16 C 0.2547(8) 0.8025(11) 0.0668(6) 0.093(3) Uani 1 1 d . . . H16 H 0.1755 0.7989 0.0815 0.112 Uiso 1 1 calc R . . C17 C 0.2898(10) 0.7276(13) 0.0096(6) 0.103(3) Uani 1 1 d . . . H17 H 0.2326 0.6760 -0.0163 0.124 Uiso 1 1 calc R . . C18 C 0.4071(10) 0.7251(11) -0.0116(5) 0.096(3) Uani 1 1 d . . . C19 C 0.4833(10) 0.8085(17) 0.0262(6) 0.126(4) Uani 1 1 d . . . H19 H 0.5630 0.8114 0.0123 0.151 Uiso 1 1 calc R . . C20 C 0.4540(8) 0.8858(12) 0.0810(6) 0.102(3) Uani 1 1 d . . . H20 H 0.5113 0.9411 0.1048 0.122 Uiso 1 1 calc R . . C21 C 0.4445(12) 0.6398(15) -0.0746(6) 0.133(4) Uani 1 1 d . . . H21A H 0.4402 0.7000 -0.1158 0.200 Uiso 1 1 calc R . . H21B H 0.3918 0.5584 -0.0807 0.200 Uiso 1 1 calc R . . H21C H 0.5253 0.6062 -0.0677 0.200 Uiso 1 1 calc R . . O1 O 0.2260(7) 0.1910(9) 0.5091(4) 0.118(2) Uani 1 1 d U . . O2 O 0.0721(9) 0.1400(9) 0.4332(4) 0.139(3) Uani 1 1 d U . . O3 O 0.3694(6) 1.1086(7) 0.1819(3) 0.0966(19) Uani 1 1 d . . . O4 O 0.1734(5) 0.9888(6) 0.1786(3) 0.0908(18) Uani 1 1 d . . . O5 O 0.3447(5) 0.8869(6) 0.2405(3) 0.0800(16) Uani 1 1 d . . . S1 S 0.29841(19) 0.9803(2) 0.17633(12) 0.0759(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.168(7) 0.136(7) 0.089(6) 0.014(5) 0.010(6) 0.003(6) C2 0.155(7) 0.135(7) 0.095(6) -0.002(5) 0.034(6) -0.021(6) C3 0.134(6) 0.137(7) 0.103(6) -0.008(5) 0.017(5) 0.003(6) C4 0.134(5) 0.115(5) 0.056(4) 0.002(4) -0.007(4) -0.028(4) C5 0.158(7) 0.100(5) 0.059(4) 0.005(4) -0.006(5) -0.021(5) C6 0.172(7) 0.096(5) 0.066(5) 0.008(4) 0.003(5) -0.027(5) C7 0.195(7) 0.105(6) 0.073(5) 0.006(5) 0.004(5) -0.048(6) C8 0.115(7) 0.079(5) 0.060(5) -0.005(4) -0.002(4) -0.006(5) C9 0.083(5) 0.071(5) 0.044(4) 0.006(3) -0.007(3) -0.006(4) C10 0.078(5) 0.079(6) 0.081(6) 0.014(4) 0.007(4) -0.007(4) C11 0.080(6) 0.079(5) 0.074(5) 0.003(4) 0.016(4) 0.012(4) C12 0.066(4) 0.073(5) 0.055(4) 0.009(4) -0.011(3) 0.001(4) C13 0.060(4) 0.093(6) 0.080(6) 0.017(5) 0.001(4) 0.013(4) C14 0.099(6) 0.069(5) 0.063(5) 0.021(4) 0.005(4) 0.020(4) C15 0.079(5) 0.070(5) 0.073(5) 0.028(4) -0.009(4) -0.004(4) C16 0.058(5) 0.112(7) 0.108(8) 0.001(6) -0.012(5) 0.004(5) C17 0.089(7) 0.136(9) 0.084(7) -0.015(6) -0.017(5) -0.010(6) C18 0.111(8) 0.100(7) 0.077(6) 0.013(5) -0.009(6) 0.007(6) C19 0.090(7) 0.205(13) 0.083(7) -0.015(8) 0.009(6) -0.037(8) C20 0.073(6) 0.119(8) 0.114(9) -0.010(7) 0.014(5) -0.015(5) C21 0.154(11) 0.155(11) 0.092(8) -0.013(8) 0.010(7) 0.026(9) O1 0.128(5) 0.143(5) 0.083(4) 0.029(4) 0.009(4) 0.011(4) O2 0.199(6) 0.130(5) 0.088(4) -0.004(4) 0.002(4) -0.079(5) O3 0.104(4) 0.078(4) 0.107(5) 0.002(3) -0.003(3) -0.012(3) O4 0.085(4) 0.079(4) 0.108(5) 0.012(3) -0.004(3) 0.009(3) O5 0.076(3) 0.072(3) 0.092(4) 0.008(3) -0.014(3) -0.008(3) S1 0.0764(14) 0.0620(12) 0.0893(16) 0.0099(10) -0.0023(10) -0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.371(13) . ? C1 C2 1.392(17) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.490(17) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.480(15) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O1 1.331(13) . ? C4 O2 1.376(12) . ? C4 C5 1.518(13) . ? C5 C6 1.435(14) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.456(13) . ? C6 C7 1.517(14) . ? C6 H6 0.9800 . ? C7 O2 1.330(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.485(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.352(11) . ? C9 C10 1.374(12) . ? C10 C11 1.328(11) . ? C10 H10 0.9300 . ? C11 C12 1.349(11) . ? C11 H11 0.9300 . ? C12 C13 1.343(11) . ? C12 O5 1.428(9) . ? C13 C14 1.368(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C20 1.356(12) . ? C15 C16 1.372(12) . ? C15 S1 1.723(9) . ? C16 C17 1.350(14) . ? C16 H16 0.9300 . ? C17 C18 1.373(15) . ? C17 H17 0.9300 . ? C18 C19 1.346(15) . ? C18 C21 1.496(15) . ? C19 C20 1.307(15) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O3 S1 1.428(6) . ? O4 S1 1.396(6) . ? O5 S1 1.574(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 107.4(11) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C1 C2 C3 105.8(10) . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C4 C3 C2 101.7(10) . . ? C4 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? C4 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.3 . . ? O1 C4 O2 114.1(10) . . ? O1 C4 C3 103.7(8) . . ? O2 C4 C3 108.6(10) . . ? O1 C4 C5 111.5(9) . . ? O2 C4 C5 102.3(7) . . ? C3 C4 C5 117.1(10) . . ? C6 C5 C4 105.4(8) . . ? C6 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? C6 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C5 C6 C8 118.2(10) . . ? C5 C6 C7 102.4(9) . . ? C8 C6 C7 111.5(9) . . ? C5 C6 H6 108.1 . . ? C8 C6 H6 108.1 . . ? C7 C6 H6 108.1 . . ? O2 C7 C6 108.7(9) . . ? O2 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? C6 C8 C9 115.4(8) . . ? C6 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C6 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C14 C9 C10 118.2(7) . . ? C14 C9 C8 122.0(8) . . ? C10 C9 C8 119.8(8) . . ? C11 C10 C9 121.7(8) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 119.1(8) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 121.4(8) . . ? C13 C12 O5 119.4(7) . . ? C11 C12 O5 119.1(7) . . ? C12 C13 C14 119.0(8) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C9 C14 C13 120.5(8) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C20 C15 C16 119.9(9) . . ? C20 C15 S1 119.7(7) . . ? C16 C15 S1 120.3(7) . . ? C17 C16 C15 118.5(9) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C16 C17 C18 122.1(9) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 115.4(10) . . ? C19 C18 C21 123.2(11) . . ? C17 C18 C21 121.3(11) . . ? C20 C19 C18 125.1(11) . . ? C20 C19 H19 117.5 . . ? C18 C19 H19 117.5 . . ? C19 C20 C15 118.8(10) . . ? C19 C20 H20 120.6 . . ? C15 C20 H20 120.6 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C4 O1 C1 110.8(9) . . ? C7 O2 C4 110.4(9) . . ? C12 O5 S1 118.4(4) . . ? O4 S1 O3 120.1(4) . . ? O4 S1 O5 108.8(3) . . ? O3 S1 O5 103.0(3) . . ? O4 S1 C15 108.9(4) . . ? O3 S1 C15 109.9(4) . . ? O5 S1 C15 105.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -2.2(15) . . . . ? C1 C2 C3 C4 19.9(14) . . . . ? C2 C3 C4 O1 -31.0(12) . . . . ? C2 C3 C4 O2 90.7(11) . . . . ? C2 C3 C4 C5 -154.2(10) . . . . ? O1 C4 C5 C6 90.8(11) . . . . ? O2 C4 C5 C6 -31.5(13) . . . . ? C3 C4 C5 C6 -150.1(11) . . . . ? C4 C5 C6 C8 142.5(10) . . . . ? C4 C5 C6 C7 19.6(13) . . . . ? C5 C6 C7 O2 -1.1(14) . . . . ? C8 C6 C7 O2 -128.5(11) . . . . ? C5 C6 C8 C9 55.1(14) . . . . ? C7 C6 C8 C9 173.4(9) . . . . ? C6 C8 C9 C14 82.0(11) . . . . ? C6 C8 C9 C10 -97.9(11) . . . . ? C14 C9 C10 C11 -0.9(12) . . . . ? C8 C9 C10 C11 179.0(8) . . . . ? C9 C10 C11 C12 -0.3(13) . . . . ? C10 C11 C12 C13 1.5(13) . . . . ? C10 C11 C12 O5 -177.1(7) . . . . ? C11 C12 C13 C14 -1.4(12) . . . . ? O5 C12 C13 C14 177.2(7) . . . . ? C10 C9 C14 C13 0.9(12) . . . . ? C8 C9 C14 C13 -178.9(7) . . . . ? C12 C13 C14 C9 0.1(12) . . . . ? C20 C15 C16 C17 -1.2(13) . . . . ? S1 C15 C16 C17 -179.5(8) . . . . ? C15 C16 C17 C18 3.2(16) . . . . ? C16 C17 C18 C19 -3.5(16) . . . . ? C16 C17 C18 C21 179.2(10) . . . . ? C17 C18 C19 C20 1.9(19) . . . . ? C21 C18 C19 C20 179.2(13) . . . . ? C18 C19 C20 C15 0(2) . . . . ? C16 C15 C20 C19 -0.3(16) . . . . ? S1 C15 C20 C19 177.9(10) . . . . ? O2 C4 O1 C1 -85.8(11) . . . . ? C3 C4 O1 C1 32.1(12) . . . . ? C5 C4 O1 C1 159.0(10) . . . . ? C2 C1 O1 C4 -19.4(14) . . . . ? C6 C7 O2 C4 -20.4(15) . . . . ? O1 C4 O2 C7 -88.6(12) . . . . ? C3 C4 O2 C7 156.4(11) . . . . ? C5 C4 O2 C7 32.0(13) . . . . ? C13 C12 O5 S1 107.2(7) . . . . ? C11 C12 O5 S1 -74.2(8) . . . . ? C12 O5 S1 O4 53.8(6) . . . . ? C12 O5 S1 O3 -177.7(6) . . . . ? C12 O5 S1 C15 -62.6(6) . . . . ? C20 C15 S1 O4 166.6(7) . . . . ? C16 C15 S1 O4 -15.1(8) . . . . ? C20 C15 S1 O3 33.2(8) . . . . ? C16 C15 S1 O3 -148.5(7) . . . . ? C20 C15 S1 O5 -76.9(8) . . . . ? C16 C15 S1 O5 101.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.559 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 962593' ####################################################################### # # 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_p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 I2 O2' _chemical_formula_weight 498.12 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.616(4) _cell_length_b 22.680(12) _cell_length_c 18.209(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.020(6) _cell_angle_gamma 90.00 _cell_volume 3539(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3085 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 23.06 _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 3.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4953 _exptl_absorpt_correction_T_max 0.5516 _exptl_absorpt_process_details SADABS _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_reflns_number 13784 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6458 _reflns_number_gt 4240 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0227P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00319(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6458 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.1749(8) 0.4670(3) 0.2805(3) 0.0503(18) Uani 1 1 d . . . H1A H 0.1616 0.4521 0.2302 0.060 Uiso 1 1 calc R . . H1B H 0.0726 0.4691 0.2981 0.060 Uiso 1 1 calc R . . C2 C 0.2752(8) 0.4254(3) 0.3280(4) 0.0531(18) Uani 1 1 d . . . H2A H 0.3755 0.4211 0.3089 0.064 Uiso 1 1 calc R . . H2B H 0.2260 0.3869 0.3277 0.064 Uiso 1 1 calc R . . C3 C 0.2985(8) 0.4489(3) 0.4062(3) 0.0555(19) Uani 1 1 d . . . H3A H 0.3674 0.4228 0.4367 0.067 Uiso 1 1 calc R . . H3B H 0.1990 0.4503 0.4266 0.067 Uiso 1 1 calc R . . C4 C 0.3690(7) 0.5105(3) 0.4063(3) 0.0438(16) Uani 1 1 d . . . H4A H 0.3719 0.5270 0.4555 0.053 Uiso 1 1 calc R . . H4B H 0.4755 0.5077 0.3939 0.053 Uiso 1 1 calc R . . C5 C 0.2772(7) 0.5517(2) 0.3517(3) 0.0315(14) Uani 1 1 d . . . C6 C 0.0187(7) 0.5985(3) 0.3405(3) 0.0443(16) Uani 1 1 d . . . H6 H 0.0170 0.5866 0.2887 0.053 Uiso 1 1 calc R . . C7 C -0.1355(7) 0.5824(3) 0.3681(4) 0.0545(19) Uani 1 1 d . . . H7A H -0.1292 0.5915 0.4204 0.065 Uiso 1 1 calc R . . H7B H -0.2161 0.6073 0.3432 0.065 Uiso 1 1 calc R . . C8 C -0.1854(7) 0.5191(3) 0.3576(3) 0.0444(16) Uani 1 1 d . . . C9 C -0.2526(7) 0.4980(3) 0.2894(3) 0.0409(16) Uani 1 1 d . . . C10 C -0.2940(8) 0.4389(3) 0.2807(4) 0.0535(18) Uani 1 1 d . . . H10 H -0.3382 0.4253 0.2350 0.064 Uiso 1 1 calc R . . C11 C -0.2698(9) 0.4002(3) 0.3397(4) 0.066(2) Uani 1 1 d . . . H11 H -0.2955 0.3605 0.3334 0.079 Uiso 1 1 calc R . . C12 C -0.2073(9) 0.4207(4) 0.4077(5) 0.075(2) Uani 1 1 d . . . H12 H -0.1936 0.3953 0.4480 0.090 Uiso 1 1 calc R . . C13 C -0.1657(8) 0.4787(4) 0.4152(4) 0.058(2) Uani 1 1 d . . . H13 H -0.1220 0.4919 0.4611 0.070 Uiso 1 1 calc R . . C14 C 0.3712(7) 0.6051(3) 0.3321(3) 0.0417(16) Uani 1 1 d . . . H14A H 0.3054 0.6293 0.2977 0.050 Uiso 1 1 calc R . . H14B H 0.4577 0.5914 0.3065 0.050 Uiso 1 1 calc R . . C15 C 0.0398(8) 0.6643(3) 0.3461(4) 0.061(2) Uani 1 1 d . . . H15 H 0.0667 0.6805 0.3926 0.073 Uiso 1 1 calc R . . C16 C 0.0229(11) 0.6996(4) 0.2905(5) 0.105(3) Uani 1 1 d . . . H16A H -0.0040 0.6849 0.2432 0.126 Uiso 1 1 calc R . . H16B H 0.0376 0.7399 0.2976 0.126 Uiso 1 1 calc R . . C17 C 0.5956(8) 0.5829(3) -0.0184(4) 0.0540(18) Uani 1 1 d . . . H17A H 0.4885 0.5967 -0.0212 0.065 Uiso 1 1 calc R . . H17B H 0.5972 0.5422 -0.0023 0.065 Uiso 1 1 calc R . . C18 C 0.6505(9) 0.5860(3) -0.0939(4) 0.066(2) Uani 1 1 d . . . H18A H 0.5819 0.5629 -0.1285 0.080 Uiso 1 1 calc R . . H18B H 0.7550 0.5699 -0.0926 0.080 Uiso 1 1 calc R . . C19 C 0.6502(9) 0.6503(3) -0.1188(4) 0.065(2) Uani 1 1 d . . . H19A H 0.6925 0.6532 -0.1660 0.078 Uiso 1 1 calc R . . H19B H 0.5442 0.6653 -0.1249 0.078 Uiso 1 1 calc R . . C20 C 0.7482(7) 0.6866(3) -0.0616(3) 0.0469(17) Uani 1 1 d . . . H20A H 0.7381 0.7279 -0.0748 0.056 Uiso 1 1 calc R . . H20B H 0.8570 0.6757 -0.0621 0.056 Uiso 1 1 calc R . . C21 C 0.7016(7) 0.6783(3) 0.0164(3) 0.0362(14) Uani 1 1 d . . . C22 C 0.4755(6) 0.7018(3) 0.0821(3) 0.0355(14) Uani 1 1 d . . . H22 H 0.4919 0.6620 0.1023 0.043 Uiso 1 1 calc R . . C23 C 0.3015(6) 0.7110(2) 0.0560(3) 0.0392(15) Uani 1 1 d . . . H23A H 0.2429 0.7085 0.0986 0.047 Uiso 1 1 calc R . . H23B H 0.2878 0.7505 0.0361 0.047 Uiso 1 1 calc R . . C24 C 0.2333(6) 0.6677(3) -0.0014(3) 0.0344(14) Uani 1 1 d . . . C25 C 0.1854(7) 0.6110(3) 0.0162(3) 0.0376(15) Uani 1 1 d . . . C26 C 0.1281(7) 0.5721(3) -0.0395(4) 0.0476(17) Uani 1 1 d . . . H26 H 0.0988 0.5341 -0.0274 0.057 Uiso 1 1 calc R . . C27 C 0.1152(8) 0.5895(3) -0.1112(4) 0.0527(19) Uani 1 1 d . . . H27 H 0.0756 0.5634 -0.1479 0.063 Uiso 1 1 calc R . . C28 C 0.1600(8) 0.6452(3) -0.1301(3) 0.0559(19) Uani 1 1 d . . . H28 H 0.1525 0.6566 -0.1794 0.067 Uiso 1 1 calc R . . C29 C 0.2162(7) 0.6839(3) -0.0750(3) 0.0458(16) Uani 1 1 d . . . H29 H 0.2434 0.7219 -0.0878 0.055 Uiso 1 1 calc R . . C30 C 0.8280(7) 0.6987(3) 0.0755(3) 0.0498(17) Uani 1 1 d . . . H30A H 0.9193 0.6740 0.0733 0.060 Uiso 1 1 calc R . . H30B H 0.7912 0.6928 0.1235 0.060 Uiso 1 1 calc R . . C31 C 0.5257(7) 0.7465(3) 0.1402(4) 0.0561(19) Uani 1 1 d . . . H31 H 0.5437 0.7848 0.1249 0.067 Uiso 1 1 calc R . . C32 C 0.5458(10) 0.7356(4) 0.2104(4) 0.096(3) Uani 1 1 d . . . H32A H 0.5288 0.6978 0.2277 0.115 Uiso 1 1 calc R . . H32B H 0.5772 0.7656 0.2435 0.115 Uiso 1 1 calc R . . I1 I 0.46279(5) 0.65944(2) 0.42226(2) 0.05644(16) Uani 1 1 d . . . I2 I -0.29108(5) 0.55140(2) 0.19499(2) 0.05447(16) Uani 1 1 d . . . I3 I 0.89627(6) 0.78869(2) 0.06682(3) 0.0774(2) Uani 1 1 d . . . I4 I 0.20263(5) 0.58000(2) 0.12571(2) 0.05116(15) Uani 1 1 d . . . O1 O 0.2424(5) 0.52528(17) 0.28091(18) 0.0397(10) Uani 1 1 d . . . O2 O 0.1389(4) 0.56598(17) 0.38422(19) 0.0390(10) Uani 1 1 d . . . O3 O 0.6898(4) 0.61762(17) 0.0354(2) 0.0413(10) Uani 1 1 d . . . O4 O 0.5579(4) 0.70838(16) 0.01764(19) 0.0352(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(4) 0.052(4) 0.054(4) -0.016(3) 0.001(3) -0.012(4) C2 0.057(5) 0.038(4) 0.064(4) 0.000(3) 0.006(4) -0.003(4) C3 0.058(5) 0.054(5) 0.053(4) 0.011(4) -0.003(3) 0.004(4) C4 0.037(4) 0.051(4) 0.041(3) 0.006(3) -0.006(3) 0.002(3) C5 0.031(3) 0.039(4) 0.024(3) -0.003(3) 0.002(2) 0.004(3) C6 0.032(4) 0.048(4) 0.051(4) -0.006(3) -0.009(3) 0.008(3) C7 0.032(4) 0.075(5) 0.057(4) -0.023(4) 0.006(3) 0.004(4) C8 0.022(3) 0.060(5) 0.053(4) -0.008(4) 0.012(3) 0.008(3) C9 0.027(4) 0.053(4) 0.042(4) -0.005(3) 0.002(3) -0.002(3) C10 0.043(4) 0.065(5) 0.052(4) 0.000(4) 0.007(3) 0.001(4) C11 0.057(5) 0.066(5) 0.078(5) 0.011(5) 0.021(4) -0.007(4) C12 0.055(5) 0.102(7) 0.069(6) 0.033(5) 0.017(4) 0.003(5) C13 0.035(4) 0.100(7) 0.039(4) -0.001(4) 0.002(3) 0.001(4) C14 0.043(4) 0.041(4) 0.041(3) -0.012(3) 0.003(3) -0.005(3) C15 0.047(5) 0.051(5) 0.078(5) -0.015(4) -0.027(4) 0.009(4) C16 0.121(8) 0.056(6) 0.123(7) 0.004(6) -0.052(7) -0.008(6) C17 0.048(4) 0.042(4) 0.072(5) -0.010(4) 0.002(4) 0.002(3) C18 0.058(5) 0.075(6) 0.064(5) -0.027(4) -0.004(4) 0.016(4) C19 0.062(5) 0.086(6) 0.047(4) -0.010(4) 0.008(4) 0.023(5) C20 0.039(4) 0.042(4) 0.063(4) 0.005(3) 0.022(3) 0.010(3) C21 0.030(4) 0.033(4) 0.045(4) 0.000(3) -0.001(3) 0.005(3) C22 0.027(3) 0.032(3) 0.047(4) -0.002(3) 0.001(3) 0.003(3) C23 0.030(4) 0.034(4) 0.053(4) -0.001(3) 0.003(3) 0.005(3) C24 0.018(3) 0.043(4) 0.042(3) 0.000(3) -0.001(3) 0.007(3) C25 0.030(4) 0.044(4) 0.039(3) 0.002(3) 0.002(3) 0.006(3) C26 0.039(4) 0.042(4) 0.062(4) 0.000(3) 0.008(3) -0.003(3) C27 0.043(4) 0.063(5) 0.049(4) -0.022(4) -0.010(3) -0.003(4) C28 0.058(5) 0.074(6) 0.035(4) -0.001(4) -0.002(3) 0.014(4) C29 0.045(4) 0.047(4) 0.045(4) 0.011(3) 0.001(3) 0.006(3) C30 0.036(4) 0.041(4) 0.070(4) -0.001(3) -0.006(3) 0.004(3) C31 0.046(4) 0.062(5) 0.060(5) -0.017(4) 0.003(4) -0.010(4) C32 0.111(8) 0.116(8) 0.060(5) -0.028(5) 0.007(5) -0.030(6) I1 0.0444(3) 0.0600(3) 0.0630(3) -0.0171(2) -0.0040(2) -0.0064(2) I2 0.0483(3) 0.0607(3) 0.0516(3) 0.0017(2) -0.0081(2) 0.0076(2) I3 0.0516(3) 0.0498(3) 0.1316(5) -0.0201(3) 0.0133(3) -0.0087(3) I4 0.0518(3) 0.0521(3) 0.0496(3) 0.0107(2) 0.0056(2) -0.0008(2) O1 0.046(3) 0.044(3) 0.029(2) -0.0005(19) -0.0002(18) -0.002(2) O2 0.029(2) 0.054(3) 0.033(2) -0.0010(19) 0.0000(18) 0.002(2) O3 0.039(3) 0.032(2) 0.052(2) -0.004(2) -0.002(2) 0.005(2) O4 0.028(2) 0.035(2) 0.042(2) 0.0043(19) 0.0026(18) 0.0053(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.445(7) . ? C1 C2 1.494(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.513(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.523(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.523(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O2 1.422(6) . ? C5 O1 1.425(6) . ? C5 C14 1.521(8) . ? C6 O2 1.441(6) . ? C6 C15 1.505(9) . ? C6 C7 1.514(9) . ? C6 H6 0.9800 . ? C7 C8 1.505(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.388(9) . ? C8 C9 1.400(8) . ? C9 C10 1.391(8) . ? C9 I2 2.101(6) . ? C10 C11 1.387(9) . ? C10 H10 0.9300 . ? C11 C12 1.378(10) . ? C11 H11 0.9300 . ? C12 C13 1.368(10) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 I1 2.137(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.287(9) . ? C15 H15 0.9300 . ? C16 H16A 0.9300 . ? C16 H16B 0.9300 . ? C17 O3 1.439(7) . ? C17 C18 1.502(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.528(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.514(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.528(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 O4 1.416(6) . ? C21 O3 1.424(7) . ? C21 C30 1.522(8) . ? C22 O4 1.441(6) . ? C22 C31 1.498(8) . ? C22 C23 1.538(7) . ? C22 H22 0.9800 . ? C23 C24 1.508(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C29 1.382(8) . ? C24 C25 1.399(8) . ? C25 C26 1.395(8) . ? C25 I4 2.104(6) . ? C26 C27 1.358(9) . ? C26 H26 0.9300 . ? C27 C28 1.375(9) . ? C27 H27 0.9300 . ? C28 C29 1.382(8) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 I3 2.134(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.295(9) . ? C31 H31 0.9300 . ? C32 H32A 0.9300 . ? C32 H32B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 111.5(5) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 109.5(5) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 109.7(5) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 112.5(5) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O2 C5 O1 111.5(4) . . ? O2 C5 C14 114.0(5) . . ? O1 C5 C14 100.9(4) . . ? O2 C5 C4 105.6(4) . . ? O1 C5 C4 112.2(4) . . ? C14 C5 C4 112.9(5) . . ? O2 C6 C15 113.3(5) . . ? O2 C6 C7 107.3(5) . . ? C15 C6 C7 108.7(5) . . ? O2 C6 H6 109.1 . . ? C15 C6 H6 109.1 . . ? C7 C6 H6 109.1 . . ? C8 C7 C6 115.9(5) . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7B 108.3 . . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C13 C8 C9 116.8(6) . . ? C13 C8 C7 121.5(6) . . ? C9 C8 C7 121.7(6) . . ? C10 C9 C8 120.6(6) . . ? C10 C9 I2 116.5(4) . . ? C8 C9 I2 122.9(5) . . ? C11 C10 C9 120.4(6) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.7(7) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 119.2(7) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 123.4(7) . . ? C12 C13 H13 118.3 . . ? C8 C13 H13 118.3 . . ? C5 C14 I1 116.2(4) . . ? C5 C14 H14A 108.2 . . ? I1 C14 H14A 108.2 . . ? C5 C14 H14B 108.2 . . ? I1 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C6 124.1(7) . . ? C16 C15 H15 117.9 . . ? C6 C15 H15 117.9 . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? O3 C17 C18 112.8(6) . . ? O3 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? O3 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 C19 109.0(6) . . ? C17 C18 H18A 109.9 . . ? C19 C18 H18A 109.9 . . ? C17 C18 H18B 109.9 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C20 C19 C18 109.3(5) . . ? C20 C19 H19A 109.8 . . ? C18 C19 H19A 109.8 . . ? C20 C19 H19B 109.8 . . ? C18 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? C19 C20 C21 113.0(5) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? O4 C21 O3 112.2(5) . . ? O4 C21 C30 113.8(5) . . ? O3 C21 C30 100.8(4) . . ? O4 C21 C20 105.7(5) . . ? O3 C21 C20 112.2(5) . . ? C30 C21 C20 112.4(5) . . ? O4 C22 C31 112.0(5) . . ? O4 C22 C23 106.4(4) . . ? C31 C22 C23 109.0(5) . . ? O4 C22 H22 109.8 . . ? C31 C22 H22 109.8 . . ? C23 C22 H22 109.8 . . ? C24 C23 C22 114.9(5) . . ? C24 C23 H23A 108.5 . . ? C22 C23 H23A 108.5 . . ? C24 C23 H23B 108.5 . . ? C22 C23 H23B 108.5 . . ? H23A C23 H23B 107.5 . . ? C29 C24 C25 117.6(6) . . ? C29 C24 C23 119.6(6) . . ? C25 C24 C23 122.8(5) . . ? C26 C25 C24 120.3(5) . . ? C26 C25 I4 117.5(4) . . ? C24 C25 I4 122.1(4) . . ? C27 C26 C25 120.2(6) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 120.7(6) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C29 119.2(6) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? C28 C29 C24 122.0(6) . . ? C28 C29 H29 119.0 . . ? C24 C29 H29 119.0 . . ? C21 C30 I3 114.9(4) . . ? C21 C30 H30A 108.5 . . ? I3 C30 H30A 108.5 . . ? C21 C30 H30B 108.5 . . ? I3 C30 H30B 108.5 . . ? H30A C30 H30B 107.5 . . ? C32 C31 C22 124.6(7) . . ? C32 C31 H31 117.7 . . ? C22 C31 H31 117.7 . . ? C31 C32 H32A 120.0 . . ? C31 C32 H32B 120.0 . . ? H32A C32 H32B 120.0 . . ? C5 O1 C1 115.8(4) . . ? C5 O2 C6 118.2(4) . . ? C21 O3 C17 114.4(4) . . ? C21 O4 C22 118.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 58.1(7) . . . . ? C1 C2 C3 C4 -56.9(7) . . . . ? C2 C3 C4 C5 52.1(7) . . . . ? C3 C4 C5 O2 74.1(6) . . . . ? C3 C4 C5 O1 -47.6(7) . . . . ? C3 C4 C5 C14 -160.8(5) . . . . ? O2 C6 C7 C8 -64.5(7) . . . . ? C15 C6 C7 C8 172.5(6) . . . . ? C6 C7 C8 C13 100.5(7) . . . . ? C6 C7 C8 C9 -79.0(7) . . . . ? C13 C8 C9 C10 -1.2(9) . . . . ? C7 C8 C9 C10 178.3(6) . . . . ? C13 C8 C9 I2 -179.5(4) . . . . ? C7 C8 C9 I2 0.1(8) . . . . ? C8 C9 C10 C11 0.3(10) . . . . ? I2 C9 C10 C11 178.7(5) . . . . ? C9 C10 C11 C12 1.4(10) . . . . ? C10 C11 C12 C13 -2.0(11) . . . . ? C11 C12 C13 C8 1.1(11) . . . . ? C9 C8 C13 C12 0.5(10) . . . . ? C7 C8 C13 C12 -179.0(6) . . . . ? O2 C5 C14 I1 63.0(6) . . . . ? O1 C5 C14 I1 -177.5(3) . . . . ? C4 C5 C14 I1 -57.5(6) . . . . ? O2 C6 C15 C16 135.9(8) . . . . ? C7 C6 C15 C16 -104.8(9) . . . . ? O3 C17 C18 C19 -57.9(7) . . . . ? C17 C18 C19 C20 55.4(7) . . . . ? C18 C19 C20 C21 -52.3(7) . . . . ? C19 C20 C21 O4 -73.1(6) . . . . ? C19 C20 C21 O3 49.5(7) . . . . ? C19 C20 C21 C30 162.2(5) . . . . ? O4 C22 C23 C24 60.7(6) . . . . ? C31 C22 C23 C24 -178.4(5) . . . . ? C22 C23 C24 C29 -99.3(6) . . . . ? C22 C23 C24 C25 80.7(7) . . . . ? C29 C24 C25 C26 2.3(9) . . . . ? C23 C24 C25 C26 -177.7(5) . . . . ? C29 C24 C25 I4 -179.7(4) . . . . ? C23 C24 C25 I4 0.3(8) . . . . ? C24 C25 C26 C27 -1.5(9) . . . . ? I4 C25 C26 C27 -179.6(5) . . . . ? C25 C26 C27 C28 0.9(10) . . . . ? C26 C27 C28 C29 -1.1(10) . . . . ? C27 C28 C29 C24 2.0(10) . . . . ? C25 C24 C29 C28 -2.6(9) . . . . ? C23 C24 C29 C28 177.5(6) . . . . ? O4 C21 C30 I3 -62.6(6) . . . . ? O3 C21 C30 I3 177.2(4) . . . . ? C20 C21 C30 I3 57.6(6) . . . . ? O4 C22 C31 C32 -139.9(7) . . . . ? C23 C22 C31 C32 102.6(8) . . . . ? O2 C5 O1 C1 -68.8(6) . . . . ? C14 C5 O1 C1 169.9(5) . . . . ? C4 C5 O1 C1 49.5(6) . . . . ? C2 C1 O1 C5 -55.6(7) . . . . ? O1 C5 O2 C6 -49.9(6) . . . . ? C14 C5 O2 C6 63.5(6) . . . . ? C4 C5 O2 C6 -172.1(4) . . . . ? C15 C6 O2 C5 -87.7(6) . . . . ? C7 C6 O2 C5 152.3(5) . . . . ? O4 C21 O3 C17 68.3(6) . . . . ? C30 C21 O3 C17 -170.3(5) . . . . ? C20 C21 O3 C17 -50.5(6) . . . . ? C18 C17 O3 C21 56.4(7) . . . . ? O3 C21 O4 C22 49.8(6) . . . . ? C30 C21 O4 C22 -63.8(6) . . . . ? C20 C21 O4 C22 172.3(4) . . . . ? C31 C22 O4 C21 88.2(6) . . . . ? C23 C22 O4 C21 -152.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.716 _refine_diff_density_min -0.871 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 962594'