# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Brian Skelton' _publ_contact_author_email brian.skelton@uwa.edu.au loop_ _publ_author_name G.Flematti A.Scaffidi E.Ghisalberti data_asuv2 _database_code_depnum_ccdc_archive 'CCDC 837151' #TrackingRef 'web_deposit_cif_file_0_BrianSkelton_1311842493.asuv2.cif' _audit_creation_date 2011-01-18T09:17:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C16 H12 O6' _chemical_formula_moiety 'C16 H12 O6' _chemical_formula_weight 300.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.8238(2) _cell_length_b 11.0492(3) _cell_length_c 16.3885(4) _cell_angle_alpha 90 _cell_angle_beta 100.760(2) _cell_angle_gamma 90 _cell_volume 1213.93(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9977 _cell_measurement_theta_min 3.7918 _cell_measurement_theta_max 32.5756 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.90627 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 0.0160134143 _diffrn_orient_matrix_ub_12 -0.0056400863 _diffrn_orient_matrix_ub_13 0.0438660707 _diffrn_orient_matrix_ub_21 0.1044184108 _diffrn_orient_matrix_ub_22 0.0048245384 _diffrn_orient_matrix_ub_23 0.0017833279 _diffrn_orient_matrix_ub_31 -0.0064108658 _diffrn_orient_matrix_ub_32 0.0638358566 _diffrn_orient_matrix_ub_33 0.0037662059 _diffrn_measurement_device_type 'Oxford Diffraction Gemini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_number 22968 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.9 _diffrn_reflns_theta_max 32.63 _diffrn_reflns_theta_full 32 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.952 _reflns_number_total 4234 _reflns_number_gt 3131 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0707P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4234 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.057 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.474 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O11 O 0.47656(11) 0.60417(7) 0.21039(4) 0.01343(16) Uani 1 1 d . . . C12 C 0.38671(16) 0.66750(9) 0.13975(6) 0.0130(2) Uani 1 1 d . . . O12 O 0.48421(12) 0.70375(7) 0.09079(5) 0.01836(17) Uani 1 1 d . . . C13 C 0.17242(15) 0.68323(9) 0.14169(6) 0.0127(2) Uani 1 1 d . . . C13A C 0.14232(15) 0.63974(9) 0.21452(6) 0.01121(18) Uani 1 1 d . . . C13B C 0.03212(17) 0.73933(10) 0.07098(7) 0.0165(2) Uani 1 1 d . . . H13A H 0.0015 0.681 0.0254 0.025 Uiso 1 1 calc R . . H13B H 0.0941 0.8114 0.0518 0.025 Uiso 1 1 calc R . . H13C H -0.0913 0.7625 0.0894 0.025 Uiso 1 1 calc R . . C14 C -0.02772(15) 0.63197(9) 0.25857(6) 0.01211(19) Uani 1 1 d . . . H14 H -0.1573 0.6617 0.2258 0.015 Uiso 1 1 calc R . . C15 C -0.03790(16) 0.50234(9) 0.29736(6) 0.0140(2) Uani 1 1 d . . . H15 H -0.1767 0.4691 0.2858 0.017 Uiso 1 1 calc R . . O16 O 0.10316(12) 0.41696(6) 0.27731(5) 0.01523(16) Uani 1 1 d . . . C17 C 0.30093(16) 0.46119(9) 0.29838(7) 0.0138(2) Uani 1 1 d . . . H17 H 0.4011 0.4007 0.2867 0.017 Uiso 1 1 calc R . . C17A C 0.33238(15) 0.58828(9) 0.26112(6) 0.01175(19) Uani 1 1 d . . . O21 O 0.57506(11) 0.69862(7) 0.37410(5) 0.01395(16) Uani 1 1 d . . . C22 C 0.54168(15) 0.81825(9) 0.39597(6) 0.01221(19) Uani 1 1 d . . . O22 O 0.67880(11) 0.88796(7) 0.41080(5) 0.01636(17) Uani 1 1 d . . . C23 C 0.32576(15) 0.83525(9) 0.39364(6) 0.01125(19) Uani 1 1 d . . . C23A C 0.23596(15) 0.73103(9) 0.36763(6) 0.01124(19) Uani 1 1 d . . . C23B C 0.23914(16) 0.95102(9) 0.41706(6) 0.0142(2) Uani 1 1 d . . . H23A H 0.0932 0.9456 0.405 0.021 Uiso 1 1 calc R . . H23B H 0.2823 1.0176 0.3851 0.021 Uiso 1 1 calc R . . H23C H 0.2849 0.966 0.4765 0.021 Uiso 1 1 calc R . . C24 C 0.02873(15) 0.68663(9) 0.34998(6) 0.01208(19) Uani 1 1 d . . . H24 H -0.0715 0.7448 0.3646 0.014 Uiso 1 1 calc R . . C25 C 0.01666(16) 0.55589(9) 0.38644(6) 0.0145(2) Uani 1 1 d . . . H25 H -0.0962 0.5482 0.4173 0.017 Uiso 1 1 calc R . . O26 O 0.19894(12) 0.51008(7) 0.43375(5) 0.01545(16) Uani 1 1 d . . . C27 C 0.35616(16) 0.51396(9) 0.38815(6) 0.0137(2) Uani 1 1 d . . . H27 H 0.4828 0.4789 0.4199 0.016 Uiso 1 1 calc R . . C27A C 0.38784(15) 0.64116(9) 0.35222(6) 0.01152(19) 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 O11 0.0100(3) 0.0172(4) 0.0139(3) -0.0006(3) 0.0041(3) 0.0016(3) C12 0.0134(5) 0.0118(4) 0.0141(4) -0.0028(4) 0.0031(4) -0.0007(4) O12 0.0184(4) 0.0204(4) 0.0183(4) 0.0001(3) 0.0086(3) -0.0013(3) C13 0.0120(4) 0.0114(4) 0.0148(5) -0.0023(4) 0.0030(4) -0.0003(4) C13A 0.0098(4) 0.0094(4) 0.0144(4) -0.0017(3) 0.0022(4) -0.0004(3) C13B 0.0171(5) 0.0176(5) 0.0147(5) 0.0005(4) 0.0027(4) 0.0037(4) C14 0.0094(4) 0.0130(4) 0.0142(4) -0.0011(4) 0.0029(4) -0.0014(3) C15 0.0130(5) 0.0128(4) 0.0165(5) -0.0013(4) 0.0037(4) -0.0021(4) O16 0.0152(4) 0.0112(3) 0.0195(4) -0.0019(3) 0.0038(3) -0.0015(3) C17 0.0136(5) 0.0119(4) 0.0159(5) -0.0014(4) 0.0027(4) 0.0004(4) C17A 0.0103(4) 0.0131(4) 0.0124(4) -0.0009(3) 0.0034(4) 0.0001(3) O21 0.0094(3) 0.0145(3) 0.0178(4) -0.0030(3) 0.0022(3) -0.0005(3) C22 0.0116(4) 0.0141(5) 0.0110(4) -0.0004(3) 0.0024(4) 0.0010(3) O22 0.0135(4) 0.0174(4) 0.0181(4) -0.0025(3) 0.0029(3) -0.0035(3) C23 0.0103(4) 0.0127(4) 0.0109(4) 0.0003(3) 0.0023(3) 0.0002(3) C23A 0.0101(4) 0.0132(4) 0.0110(4) 0.0004(3) 0.0033(4) 0.0007(3) C23B 0.0144(5) 0.0119(4) 0.0166(5) -0.0010(4) 0.0036(4) 0.0011(4) C24 0.0100(4) 0.0132(4) 0.0138(4) -0.0015(4) 0.0041(4) -0.0010(3) C25 0.0132(5) 0.0150(5) 0.0160(5) 0.0002(4) 0.0045(4) -0.0018(4) O26 0.0157(4) 0.0167(4) 0.0145(3) 0.0024(3) 0.0044(3) 0.0001(3) C27 0.0136(5) 0.0131(4) 0.0144(5) 0.0007(4) 0.0027(4) 0.0012(4) C27A 0.0085(4) 0.0127(4) 0.0134(4) -0.0017(4) 0.0023(4) -0.0004(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 C12 1.3932(12) . ? O11 C17A 1.4126(12) . ? C12 O12 1.2026(13) . ? C12 C13 1.4787(15) . ? C13 C13A 1.3376(14) . ? C13 C13B 1.4931(14) . ? C13A C14 1.4791(14) . ? C13A C17A 1.4895(14) . ? C13B H13A 0.98 . ? C13B H13B 0.98 . ? C13B H13C 0.98 . ? C14 C15 1.5739(15) . ? C14 C24 1.5943(14) . ? C14 H14 1 . ? C15 O16 1.4292(13) . ? C15 C25 1.5547(15) . ? C15 H15 1 . ? O16 C17 1.4161(13) . ? C17 C27 1.5619(14) . ? C17 C17A 1.5620(14) . ? C17 H17 1 . ? C17A C27A 1.5819(14) . ? O21 C22 1.3994(12) . ? O21 C27A 1.4116(12) . ? C22 O22 1.2012(12) . ? C22 C23 1.4787(14) . ? C23 C23A 1.3363(14) . ? C23 C23B 1.4892(14) . ? C23A C24 1.4735(14) . ? C23A C27A 1.4906(14) . ? C23B H23A 0.98 . ? C23B H23B 0.98 . ? C23B H23C 0.98 . ? C24 C25 1.5712(15) . ? C24 H24 1 . ? C25 O26 1.4298(13) . ? C25 H25 1 . ? O26 C27 1.4180(13) . ? C27 C27A 1.5544(14) . ? C27 H27 1 . ? 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 O11 C17A 107.74(8) . . ? O12 C12 O11 120.62(10) . . ? O12 C12 C13 130.37(10) . . ? O11 C12 C13 108.95(8) . . ? C13A C13 C12 107.11(9) . . ? C13A C13 C13B 131.19(10) . . ? C12 C13 C13B 121.70(9) . . ? C13 C13A C14 136.18(10) . . ? C13 C13A C17A 109.30(9) . . ? C14 C13A C17A 114.51(9) . . ? C13 C13B H13A 109.5 . . ? C13 C13B H13B 109.5 . . ? H13A C13B H13B 109.5 . . ? C13 C13B H13C 109.5 . . ? H13A C13B H13C 109.5 . . ? H13B C13B H13C 109.5 . . ? C13A C14 C15 110.35(8) . . ? C13A C14 C24 111.27(8) . . ? C15 C14 C24 89.22(7) . . ? C13A C14 H14 114.5 . . ? C15 C14 H14 114.5 . . ? C24 C14 H14 114.5 . . ? O16 C15 C25 114.43(9) . . ? O16 C15 C14 115.18(8) . . ? C25 C15 C14 90.69(7) . . ? O16 C15 H15 111.7 . . ? C25 C15 H15 111.7 . . ? C14 C15 H15 111.7 . . ? C17 O16 C15 111.61(8) . . ? O16 C17 C27 114.19(9) . . ? O16 C17 C17A 114.16(8) . . ? C27 C17 C17A 90.34(7) . . ? O16 C17 H17 112.2 . . ? C27 C17 H17 112.2 . . ? C17A C17 H17 112.2 . . ? O11 C17A C13A 106.63(8) . . ? O11 C17A C17 120.23(8) . . ? C13A C17A C17 111.93(8) . . ? O11 C17A C27A 116.06(8) . . ? C13A C17A C27A 112.02(8) . . ? C17 C17A C27A 89.38(7) . . ? C22 O21 C27A 107.88(8) . . ? O22 C22 O21 119.98(9) . . ? O22 C22 C23 131.19(9) . . ? O21 C22 C23 108.81(8) . . ? C23A C23 C22 107.11(9) . . ? C23A C23 C23B 129.94(10) . . ? C22 C23 C23B 122.95(9) . . ? C23 C23A C24 135.70(10) . . ? C23 C23A C27A 109.64(9) . . ? C24 C23A C27A 114.65(9) . . ? C23 C23B H23A 109.5 . . ? C23 C23B H23B 109.5 . . ? H23A C23B H23B 109.5 . . ? C23 C23B H23C 109.5 . . ? H23A C23B H23C 109.5 . . ? H23B C23B H23C 109.5 . . ? C23A C24 C25 110.36(8) . . ? C23A C24 C14 111.42(8) . . ? C25 C24 C14 89.34(7) . . ? C23A C24 H24 114.4 . . ? C25 C24 H24 114.4 . . ? C14 C24 H24 114.4 . . ? O26 C25 C15 113.95(9) . . ? O26 C25 C24 115.44(8) . . ? C15 C25 C24 90.76(7) . . ? O26 C25 H25 111.7 . . ? C15 C25 H25 111.7 . . ? C24 C25 H25 111.7 . . ? C27 O26 C25 111.76(8) . . ? O26 C27 C27A 113.54(8) . . ? O26 C27 C17 114.32(9) . . ? C27A C27 C17 90.39(7) . . ? O26 C27 H27 112.3 . . ? C27A C27 H27 112.3 . . ? C17 C27 H27 112.3 . . ? O21 C27A C23A 106.39(8) . . ? O21 C27A C27 119.58(8) . . ? C23A C27A C27 112.82(8) . . ? O21 C27A C17A 116.84(8) . . ? C23A C27A C17A 110.77(8) . . ? C27 C27A C17A 89.88(7) . . ? data_asuv1 _database_code_depnum_ccdc_archive 'CCDC 837152' _publ_section_references ; Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. McPhillips, T.M., McPhillips,S.E., Chiu,H.J., Cohen, A.E., Deacon,A.M. Ellis,P.J., Garman, E., Gonzalez,A., Sauter,N.K., Phizackerley, R.P., Soltis, S.M., and Kuhn,P. (2002). J. Synchrotron Radiat., 9, 401-406. Kabsch, W. (2010), Acta Cryst., D66, 125-132. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _vrf_ATOM007_asuv1 ; PROBLEM: _atom_site_aniso_label is missing Unique label identifying the atom site. RESPONSE: All atoms were refined with isotropic displacement parameters. Anisotropic refinement resulted in many atoms with unacceptable ellipsoids. even after the application of reasonable restraints. ; _vrf_DIFMX01_asuv1 ; PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00 _refine_diff_density_max given = 1.817 Test value = 1.600 RESPONSE: The largest peak is at 1.82 Angstroms from C112. Attempts to obtain a disordered model for either of the molecules were not successful. ; _vrf_RFACG01_asuv1 ; PROBLEM: The value of the R factor is > 0.20 R factor given 0.266 RESPONSE: The model was refined as a merohedral twin. There was no indication of a second twin component. Attempts to obtain a disordered model for either of the molecules were not successful. ; _vrf_RFACR01_asuv1 ; PROBLEM: The value of the weighted R factor is > 0.45 Weighted R factor given 0.569 RESPONSE: The model was refined as a merohedral twin. There was no indication of a second twin component. Attempts to obtain a disordered model for either of the molecules were not successful. ; _vrf_PLAT201_asuv1 ; PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 44 RESPONSE: All atoms were refined with isotropic displacement parameters. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 O6' _chemical_formula_sum 'C16 H12 O6' _chemical_formula_weight 300.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_int_tables_number 14 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 17.0210(5) _cell_length_b 11.9940(10) _cell_length_c 13.4560(5) _cell_angle_alpha 90.0 _cell_angle_beta 113.283(4) _cell_angle_gamma 90.0 _cell_volume 2523.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16855 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 25.9 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.005 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.123 _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 100(2) _diffrn_radiation_wavelength 0.71077 _diffrn_radiation_type synchrotron _diffrn_radiation_monochromator silicon_111 _diffrn_measurement_device_type 'Beamline MX2 at the Australian Synchrotron' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16855 _diffrn_reflns_av_R_equivalents 0.1817 _diffrn_reflns_av_sigmaI/netI 0.2194 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4267 _reflns_number_gt 2000 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips,T.M. et.al. (2002)' _computing_data_reduction 'XDS (Wabsch, W. (2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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. The crystal was treated as a merohedral twin with approximately 50/50 occupancy, the apparent symmetry of the reciprocal lattice being orthorhombic C. The geometries of the two molecules were restrained to be similar. All atoms were refined with isotropic displacement parameters. Anisotropic refinement resulted in many atoms with unacceptable ellipsoids. even after the application of reasonable restraints. The atoms of each molecule were refined with restrained displacement parameters. Attempts to obtain a disordered model for either of the molecules were not successful. ; _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^)+(0.0800P)^2^+150.0000P] 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 ? _refine_ls_number_reflns 4267 _refine_ls_number_parameters 183 _refine_ls_number_restraints 141 _refine_ls_R_factor_all 0.3714 _refine_ls_R_factor_gt 0.2660 _refine_ls_wR_factor_ref 0.5693 _refine_ls_wR_factor_gt 0.5261 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.070 _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 O111 O -0.0014(9) 0.3414(12) 0.4383(11) 0.025(3) Uiso 1 1 d DU . . C112 C -0.0763(12) 0.3940(16) 0.3855(14) 0.019(3) Uiso 1 1 d DU . . O112 O -0.1182(11) 0.4116(14) 0.4380(13) 0.036(4) Uiso 1 1 d DU . . C113 C -0.0979(11) 0.3884(15) 0.2747(14) 0.015(3) Uiso 1 1 d DU . . C114 C -0.0093(11) 0.3048(14) 0.1656(14) 0.013(3) Uiso 1 1 d DU . . H114 H -0.0531 0.3232 0.0921 0.015 Uiso 1 1 calc R . . C115 C 0.0267(12) 0.1865(16) 0.1789(15) 0.017(3) Uiso 1 1 d DU . . H115 H -0.0004 0.1421 0.1109 0.021 Uiso 1 1 calc R . . O116 O 0.0285(8) 0.1239(10) 0.2743(10) 0.013(2) Uiso 1 1 d DU . . C117 C 0.0679(11) 0.1932(15) 0.3721(14) 0.016(3) Uiso 1 1 d DU . . H117 H 0.0692 0.1543 0.4384 0.019 Uiso 1 1 calc R . . C118 C 0.0374(12) 0.3102(15) 0.3657(14) 0.016(2) Uiso 1 1 d DU . . C119 C -0.0314(11) 0.3410(15) 0.2599(13) 0.012(3) Uiso 1 1 d DU . . C110 C -0.1851(12) 0.4251(17) 0.1851(15) 0.020(4) Uiso 1 1 d DU . . H11A H -0.1847 0.4106 0.1137 0.030 Uiso 1 1 calc R . . H11B H -0.1938 0.5050 0.1925 0.030 Uiso 1 1 calc R . . H11C H -0.2316 0.3829 0.1930 0.030 Uiso 1 1 calc R . . O121 O 0.0929(8) 0.4130(10) 0.1081(9) 0.012(2) Uiso 1 1 d DU . . C122 C 0.1269(12) 0.5192(15) 0.1526(14) 0.015(3) Uiso 1 1 d DU . . O122 O 0.1328(9) 0.6001(10) 0.0932(11) 0.016(3) Uiso 1 1 d DU . . C123 C 0.1515(11) 0.5227(14) 0.2696(13) 0.010(3) Uiso 1 1 d DU . . C124 C 0.1295(11) 0.3671(14) 0.3899(14) 0.013(3) Uiso 1 1 d DU . . H124 H 0.1576 0.4117 0.4576 0.016 Uiso 1 1 calc R . . C125 C 0.1615(11) 0.2376(15) 0.3862(14) 0.017(3) Uiso 1 1 d DU . . H125 H 0.2062 0.2148 0.4577 0.021 Uiso 1 1 calc R . . O126 O 0.1843(8) 0.2135(10) 0.3084(10) 0.016(2) Uiso 1 1 d DU . . C127 C 0.1190(11) 0.2339(14) 0.1927(14) 0.015(3) Uiso 1 1 d DU . . H127 H 0.1383 0.2148 0.1335 0.017 Uiso 1 1 calc R . . C128 C 0.0843(11) 0.3460(13) 0.1889(13) 0.010(2) Uiso 1 1 d DU . . C129 C 0.1237(10) 0.4126(13) 0.2904(13) 0.006(2) Uiso 1 1 d DU . . C120 C 0.1902(11) 0.6045(13) 0.3278(13) 0.007(3) Uiso 1 1 d DU . . H12A H 0.2501 0.6042 0.3366 0.010 Uiso 1 1 calc R . . H12B H 0.1873 0.5986 0.3989 0.010 Uiso 1 1 calc R . . H12C H 0.1630 0.6742 0.2929 0.010 Uiso 1 1 calc R . . O211 O 0.5173(12) 0.3119(19) 0.4436(16) 0.084(5) Uiso 1 1 d DU . . C212 C 0.5906(15) 0.2583(16) 0.4640(19) 0.078(5) Uiso 1 1 d DU . . O212 O 0.6299(12) 0.2281(16) 0.5550(14) 0.055(5) Uiso 1 1 d DU . . C213 C 0.6056(16) 0.263(2) 0.371(2) 0.078(5) Uiso 1 1 d DU . . C214 C 0.5072(16) 0.335(2) 0.173(2) 0.087(4) Uiso 1 1 d DU . . H214 H 0.5475 0.3125 0.1390 0.105 Uiso 1 1 calc R . . C215 C 0.4762(18) 0.455(2) 0.155(2) 0.089(5) Uiso 1 1 d DU . . H215 H 0.5023 0.4974 0.1114 0.107 Uiso 1 1 calc R . . O216 O 0.4772(15) 0.5206(18) 0.2490(19) 0.086(5) Uiso 1 1 d DU . . C217 C 0.4394(17) 0.455(2) 0.310(2) 0.085(4) Uiso 1 1 d DU . . H217 H 0.4409 0.4950 0.3764 0.102 Uiso 1 1 calc R . . C218 C 0.4676(15) 0.337(2) 0.3325(19) 0.083(4) Uiso 1 1 d DU . . C219 C 0.5313(16) 0.299(2) 0.2901(19) 0.082(4) Uiso 1 1 d DU . . C210 C 0.6892(15) 0.240(3) 0.354(2) 0.046(6) Uiso 1 1 d DU . . H21A H 0.7035 0.1608 0.3655 0.070 Uiso 1 1 calc R . . H21B H 0.7359 0.2845 0.4056 0.070 Uiso 1 1 calc R . . H21C H 0.6811 0.2608 0.2800 0.070 Uiso 1 1 calc R . . O221 O 0.3940(14) 0.2330(19) 0.0219(18) 0.102(5) Uiso 1 1 d DU . . C222 C 0.3642(14) 0.125(2) 0.032(2) 0.098(5) Uiso 1 1 d DU . . O222 O 0.3579(18) 0.062(2) -0.048(2) 0.101(7) Uiso 1 1 d DU . . C223 C 0.343(2) 0.123(2) 0.126(2) 0.093(5) Uiso 1 1 d DU . . C224 C 0.3750(16) 0.279(2) 0.273(2) 0.087(4) Uiso 1 1 d DU . . H224 H 0.3492 0.2364 0.3160 0.104 Uiso 1 1 calc R . . C225 C 0.3448(17) 0.408(2) 0.236(2) 0.086(5) Uiso 1 1 d DU . . H225 H 0.3026 0.4325 0.2664 0.103 Uiso 1 1 calc R . . O226 O 0.3174(14) 0.433(2) 0.1354(18) 0.086(5) Uiso 1 1 d DU . . C227 C 0.3801(17) 0.415(2) 0.081(2) 0.089(5) Uiso 1 1 d DU . . H227 H 0.3585 0.4334 0.0022 0.106 Uiso 1 1 calc R . . C228 C 0.4109(17) 0.301(2) 0.110(2) 0.092(4) Uiso 1 1 d DU . . C229 C 0.376(2) 0.232(2) 0.177(2) 0.091(5) Uiso 1 1 d DU . . C220 C 0.306(3) 0.046(3) 0.157(3) 0.089(9) Uiso 1 1 d DU . . H22A H 0.3495 -0.0047 0.2050 0.134 Uiso 1 1 calc R . . H22B H 0.2670 0.0053 0.0939 0.134 Uiso 1 1 calc R . . H22C H 0.2742 0.0799 0.1957 0.134 Uiso 1 1 calc R . . _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 O111 C112 1.35(2) . ? O111 C118 1.43(2) . ? C112 O112 1.21(2) . ? C112 C113 1.39(2) . ? C113 C119 1.35(2) . ? C113 C110 1.56(2) . ? C114 C119 1.52(2) . ? C114 C115 1.53(2) . ? C114 C128 1.58(2) . ? C115 O116 1.48(2) . ? C115 C127 1.61(2) . ? O116 C117 1.47(2) . ? C117 C118 1.49(2) . ? C117 C125 1.62(2) . ? C118 C119 1.49(2) . ? C118 C124 1.62(2) . ? O121 C128 1.405(19) . ? O121 C122 1.43(2) . ? C122 O122 1.29(2) . ? C122 C123 1.46(2) . ? C123 C120 1.27(2) . ? C123 C129 1.47(2) . ? C124 C129 1.41(2) . ? C124 C125 1.65(2) . ? C125 O126 1.29(2) . ? O126 C127 1.53(2) . ? C127 C128 1.46(2) . ? C128 C129 1.49(2) . ? O211 C212 1.33(2) . ? O211 C218 1.43(2) . ? C212 O212 1.20(2) . ? C212 C213 1.38(3) . ? C213 C219 1.37(3) . ? C213 C210 1.55(3) . ? C214 C215 1.52(3) . ? C214 C219 1.53(3) . ? C214 C228 1.57(3) . ? C215 O216 1.49(2) . ? C215 C227 1.62(3) . ? O216 C217 1.46(2) . ? C217 C218 1.48(3) . ? C217 C225 1.62(3) . ? C218 C219 1.49(3) . ? C218 C224 1.62(3) . ? O221 C228 1.37(2) . ? O221 C222 1.42(3) . ? C222 O222 1.28(2) . ? C222 C223 1.44(3) . ? C223 C220 1.27(3) . ? C223 C229 1.49(3) . ? C224 C229 1.41(3) . ? C224 C225 1.64(3) . ? C225 O226 1.28(2) . ? O226 C227 1.53(2) . ? C227 C228 1.46(3) . ? C228 C229 1.50(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C112 O111 C118 111.0(14) . . ? O112 C112 O111 115.4(17) . . ? O112 C112 C113 132.1(19) . . ? O111 C112 C113 109.8(15) . . ? C119 C113 C112 107.2(15) . . ? C119 C113 C110 127.1(16) . . ? C112 C113 C110 125.6(16) . . ? C119 C114 C115 112.8(15) . . ? C119 C114 C128 108.0(14) . . ? C115 C114 C128 86.6(12) . . ? O116 C115 C114 116.3(14) . . ? O116 C115 C127 113.3(14) . . ? C114 C115 C127 90.7(13) . . ? C117 O116 C115 109.6(13) . . ? O116 C117 C118 117.1(14) . . ? O116 C117 C125 111.7(14) . . ? C118 C117 C125 90.1(13) . . ? O111 C118 C117 116.9(15) . . ? O111 C118 C119 100.7(14) . . ? C117 C118 C119 114.5(15) . . ? O111 C118 C124 115.1(14) . . ? C117 C118 C124 95.7(13) . . ? C119 C118 C124 114.9(14) . . ? C113 C119 C118 110.7(15) . . ? C113 C119 C114 137.8(16) . . ? C118 C119 C114 111.4(14) . . ? C128 O121 C122 109.5(12) . . ? O122 C122 O121 122.0(15) . . ? O122 C122 C123 126.1(16) . . ? O121 C122 C123 111.9(14) . . ? C120 C123 C122 123.1(16) . . ? C120 C123 C129 135.1(16) . . ? C122 C123 C129 101.7(14) . . ? C129 C124 C118 105.8(14) . . ? C129 C124 C125 103.6(13) . . ? C118 C124 C125 84.3(12) . . ? O126 C125 C117 115.5(15) . . ? O126 C125 C124 116.3(15) . . ? C117 C125 C124 89.6(12) . . ? C125 O126 C127 117.4(13) . . ? C128 C127 O126 107.6(13) . . ? C128 C127 C115 87.6(13) . . ? O126 C127 C115 110.0(13) . . ? O121 C128 C127 112.9(13) . . ? O121 C128 C129 104.8(13) . . ? C127 C128 C129 115.5(14) . . ? O121 C128 C114 115.5(14) . . ? C127 C128 C114 94.7(13) . . ? C129 C128 C114 113.8(13) . . ? C124 C129 C123 128.4(15) . . ? C124 C129 C128 119.9(14) . . ? C123 C129 C128 111.7(13) . . ? C212 O211 C218 115.9(18) . . ? O212 C212 O211 117(2) . . ? O212 C212 C213 136(2) . . ? O211 C212 C213 106.7(19) . . ? C219 C213 C212 107(2) . . ? C219 C213 C210 124(2) . . ? C212 C213 C210 130(2) . . ? C215 C214 C219 112(2) . . ? C215 C214 C228 86.6(17) . . ? C219 C214 C228 106.0(19) . . ? O216 C215 C214 118(2) . . ? O216 C215 C227 110(2) . . ? C214 C215 C227 91.0(17) . . ? C217 O216 C215 109.9(19) . . ? O216 C217 C218 116(2) . . ? O216 C217 C225 113(2) . . ? C218 C217 C225 87.5(17) . . ? O211 C218 C217 115(2) . . ? O211 C218 C219 96.6(17) . . ? C217 C218 C219 117(2) . . ? O211 C218 C224 119(2) . . ? C217 C218 C224 98.0(17) . . ? C219 C218 C224 112.8(19) . . ? C213 C219 C218 112.2(19) . . ? C213 C219 C214 134(2) . . ? C218 C219 C214 111.6(19) . . ? C228 O221 C222 114.6(19) . . ? O222 C222 O221 112(2) . . ? O222 C222 C223 139(3) . . ? O221 C222 C223 109(2) . . ? C220 C223 C222 129(3) . . ? C220 C223 C229 129(2) . . ? C222 C223 C229 102.3(19) . . ? C229 C224 C218 106(2) . . ? C229 C224 C225 103(2) . . ? C218 C224 C225 82.5(16) . . ? O226 C225 C217 115(2) . . ? O226 C225 C224 118(2) . . ? C217 C225 C224 91.5(16) . . ? C225 O226 C227 116(2) . . ? C228 C227 O226 104(2) . . ? C228 C227 C215 86.9(17) . . ? O226 C227 C215 113.0(19) . . ? O221 C228 C227 113(2) . . ? O221 C228 C229 101.5(17) . . ? C227 C228 C229 119(2) . . ? O221 C228 C214 116(2) . . ? C227 C228 C214 94.9(17) . . ? C229 C228 C214 114(2) . . ? C224 C229 C223 130(2) . . ? C224 C229 C228 119(2) . . ? C223 C229 C228 111.6(18) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.817 _refine_diff_density_min -1.408 _refine_diff_density_rms 0.304