# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global #------------------------------------------------------------------------- #3 Publication details # Provide these details if the structure has been published, # accepted or submitted for publication # The CCDC journal deposition number, eg. 182/357, # should be included only if it has been assigned by the journal _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'ks1140.cif' #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_autor ; Prof. Peter Langer Institut f\"ur Chemie Abt. Organische Chemie Universit\"at Rostock Albert-Einstein-Str. 3a 18059 Rostock Germany ; _publ_contact_author_email Anke.Spannenberg@catalysis.de _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _ccdc_journal_depnumber ? _publ_contact_author_name 'Anke Spannenberg' loop_ _publ_author_name V.Iaroshenko A.Bunescu 'Anke Spannenberg' L.Supe M.Milyutina P.Langer #------------------------------------------------------------------------- data_ks1140 _database_code_depnum_ccdc_archive 'CCDC 832478' #TrackingRef 'ks1140.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Cl2 O6' _chemical_formula_weight 387.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.4384(10) _cell_length_b 5.6289(2) _cell_length_c 22.7063(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.241(3) _cell_angle_gamma 90.00 _cell_volume 3246.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7588 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 28.41 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7898 _exptl_absorpt_correction_T_max 0.9389 _exptl_absorpt_process_details 'X-SHAPE and X-RED32 (Stoe & Cie, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25744 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.93 _reflns_number_total 3889 _reflns_number_gt 3228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3889 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.11256(4) 0.38393(19) 0.07259(5) 0.0169(2) Uani 1 1 d . . . H1 H 0.0899 0.5165 0.0475 0.020 Uiso 1 1 calc R . . C2 C 0.10578(4) 0.1702(2) 0.02763(5) 0.0193(2) Uani 1 1 d . . . C3 C 0.13793(4) 0.1811(2) -0.01154(5) 0.0206(2) Uani 1 1 d . . . C4 C 0.13187(5) 0.0089(2) -0.05873(6) 0.0257(3) Uani 1 1 d . . . H4 H 0.1094 -0.1236 -0.0626 0.031 Uiso 1 1 calc R . . C5 C 0.15827(5) 0.0310(2) -0.09939(6) 0.0295(3) Uani 1 1 d . . . H5 H 0.1545 -0.0871 -0.1307 0.035 Uiso 1 1 calc R . . C6 C 0.19045(5) 0.2272(3) -0.09441(6) 0.0286(3) Uani 1 1 d . . . H6 H 0.2076 0.2447 -0.1235 0.034 Uiso 1 1 calc R . . C7 C 0.19792(5) 0.3972(2) -0.04781(6) 0.0252(2) Uani 1 1 d . . . H7 H 0.2202 0.5299 -0.0445 0.030 Uiso 1 1 calc R . . C8 C 0.17223(4) 0.3704(2) -0.00583(5) 0.0207(2) Uani 1 1 d . . . C9 C 0.17010(4) 0.46288(19) 0.09452(5) 0.0171(2) Uani 1 1 d . . . H9 H 0.1935 0.3269 0.1161 0.021 Uiso 1 1 calc R . . C10 C 0.18366(4) 0.67608(19) 0.13887(5) 0.0182(2) Uani 1 1 d . . . H10 H 0.1636 0.8143 0.1135 0.022 Uiso 1 1 calc R . . C11 C 0.16537(4) 0.64241(18) 0.19295(5) 0.0174(2) Uani 1 1 d . . . C12 C 0.10970(4) 0.54572(19) 0.17602(5) 0.0163(2) Uani 1 1 d . . . H12 H 0.0842 0.6759 0.1551 0.020 Uiso 1 1 calc R . . C13 C 0.09693(4) 0.33080(19) 0.12971(5) 0.0166(2) Uani 1 1 d . . . C14 C 0.03694(4) 0.2669(2) 0.10448(6) 0.0213(2) Uani 1 1 d . . . H14 H 0.0293 0.1584 0.0672 0.026 Uiso 1 1 calc R . . C15 C 0.10374(4) 0.4824(2) 0.23786(5) 0.0190(2) Uani 1 1 d . . . C16 C 0.06297(5) 0.5745(3) 0.30886(6) 0.0308(3) Uani 1 1 d . . . H16A H 0.0442 0.4226 0.3023 0.046 Uiso 1 1 calc R . . H16B H 0.0414 0.6993 0.3169 0.046 Uiso 1 1 calc R . . H16C H 0.0964 0.5616 0.3454 0.046 Uiso 1 1 calc R . . C17 C 0.24178(5) 0.7416(2) 0.16251(6) 0.0288(3) Uani 1 1 d . . . H17A H 0.2477 0.8897 0.1869 0.043 Uiso 1 1 calc R . . H17B H 0.2522 0.7632 0.1261 0.043 Uiso 1 1 calc R . . H17C H 0.2628 0.6142 0.1898 0.043 Uiso 1 1 calc R . . Cl1 Cl -0.003401(11) 0.52357(5) 0.077907(14) 0.02555(8) Uani 1 1 d . . . Cl2 Cl 0.019595(13) 0.11537(6) 0.162335(17) 0.03027(9) Uani 1 1 d . . . O1 O 0.07542(4) 0.00712(16) 0.02274(4) 0.0283(2) Uani 1 1 d . . . O2 O 0.12675(3) 0.13007(14) 0.16027(4) 0.02076(17) Uani 1 1 d . . . O3 O 0.12502(4) 0.31291(16) 0.26980(4) 0.02772(19) Uani 1 1 d . . . O4 O 0.07318(3) 0.63375(15) 0.25244(4) 0.02257(18) Uani 1 1 d . . . O5 O 0.19109(3) 0.70473(16) 0.24679(4) 0.02454(18) Uani 1 1 d . . . O6 O 0.18175(3) 0.53677(15) 0.04073(4) 0.02142(18) Uani 1 1 d . . . H2 H 0.1297(7) 0.135(3) 0.1975(9) 0.041(5) Uiso 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 0.0181(5) 0.0169(5) 0.0154(5) -0.0009(4) 0.0061(4) 0.0026(4) C2 0.0204(5) 0.0199(5) 0.0164(5) -0.0014(4) 0.0057(4) 0.0026(4) C3 0.0215(5) 0.0231(5) 0.0161(5) -0.0003(4) 0.0060(4) 0.0056(4) C4 0.0289(6) 0.0266(6) 0.0210(6) -0.0040(5) 0.0085(5) 0.0043(5) C5 0.0334(7) 0.0349(7) 0.0203(6) -0.0067(5) 0.0101(5) 0.0084(5) C6 0.0283(6) 0.0407(7) 0.0193(6) -0.0002(5) 0.0116(5) 0.0093(5) C7 0.0246(6) 0.0322(6) 0.0206(6) 0.0012(5) 0.0106(5) 0.0041(5) C8 0.0221(5) 0.0239(6) 0.0157(5) -0.0007(4) 0.0068(4) 0.0064(4) C9 0.0201(5) 0.0177(5) 0.0155(5) -0.0007(4) 0.0088(4) 0.0015(4) C10 0.0211(5) 0.0163(5) 0.0183(5) -0.0016(4) 0.0086(4) -0.0003(4) C11 0.0203(5) 0.0137(5) 0.0178(5) 0.0006(4) 0.0068(4) 0.0037(4) C12 0.0183(5) 0.0158(5) 0.0154(5) 0.0001(4) 0.0069(4) 0.0030(4) C13 0.0181(5) 0.0144(5) 0.0176(5) 0.0001(4) 0.0072(4) 0.0027(4) C14 0.0206(5) 0.0214(5) 0.0237(6) -0.0033(4) 0.0104(5) 0.0001(4) C15 0.0192(5) 0.0208(5) 0.0170(5) -0.0013(4) 0.0069(4) -0.0013(4) C16 0.0291(6) 0.0459(8) 0.0233(6) -0.0024(6) 0.0166(5) -0.0024(6) C17 0.0259(6) 0.0346(7) 0.0294(7) -0.0105(5) 0.0142(5) -0.0104(5) Cl1 0.01924(13) 0.03237(16) 0.02298(15) 0.00147(11) 0.00565(11) 0.00624(11) Cl2 0.03156(16) 0.02565(15) 0.04066(18) 0.00290(12) 0.02166(14) -0.00335(12) O1 0.0327(5) 0.0250(4) 0.0308(5) -0.0105(4) 0.0161(4) -0.0071(4) O2 0.0267(4) 0.0164(4) 0.0204(4) 0.0029(3) 0.0103(3) 0.0072(3) O3 0.0367(5) 0.0268(4) 0.0215(4) 0.0066(3) 0.0131(4) 0.0065(4) O4 0.0248(4) 0.0267(4) 0.0205(4) -0.0019(3) 0.0134(3) 0.0020(3) O5 0.0255(4) 0.0289(4) 0.0172(4) -0.0031(3) 0.0058(3) -0.0018(4) O6 0.0272(4) 0.0225(4) 0.0183(4) -0.0024(3) 0.0129(3) -0.0019(3) _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 C9 1.5308(15) . ? C1 C13 1.5416(15) . ? C1 C2 1.5430(15) . ? C2 O1 1.2160(15) . ? C2 C3 1.4722(16) . ? C3 C8 1.3947(17) . ? C3 C4 1.4072(16) . ? C4 C5 1.3779(18) . ? C5 C6 1.392(2) . ? C6 C7 1.3828(18) . ? C7 C8 1.3917(17) . ? C8 O6 1.3617(14) . ? C9 O6 1.4361(13) . ? C9 C10 1.5195(15) . ? C10 C11 1.5039(15) . ? C10 C17 1.5230(16) . ? C11 O5 1.2094(14) . ? C11 C12 1.5275(15) . ? C12 C15 1.5163(15) . ? C12 C13 1.5534(15) . ? C13 O2 1.4135(13) . ? C13 C14 1.5661(15) . ? C14 Cl2 1.7757(12) . ? C14 Cl1 1.7808(12) . ? C15 O3 1.2068(14) . ? C15 O4 1.3224(14) . ? C16 O4 1.4500(15) . ? 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 C9 C1 C13 111.34(9) . . ? C9 C1 C2 107.03(9) . . ? C13 C1 C2 113.78(9) . . ? O1 C2 C3 121.52(10) . . ? O1 C2 C1 123.77(10) . . ? C3 C2 C1 114.68(10) . . ? C8 C3 C4 118.57(11) . . ? C8 C3 C2 120.88(10) . . ? C4 C3 C2 120.40(11) . . ? C5 C4 C3 120.48(12) . . ? C4 C5 C6 119.70(11) . . ? C7 C6 C5 121.12(12) . . ? C6 C7 C8 118.84(12) . . ? O6 C8 C7 117.34(11) . . ? O6 C8 C3 121.47(10) . . ? C7 C8 C3 121.19(11) . . ? O6 C9 C10 104.91(9) . . ? O6 C9 C1 109.97(9) . . ? C10 C9 C1 114.11(9) . . ? C11 C10 C9 111.59(9) . . ? C11 C10 C17 111.79(9) . . ? C9 C10 C17 112.70(9) . . ? O5 C11 C10 122.79(10) . . ? O5 C11 C12 120.19(10) . . ? C10 C11 C12 116.77(9) . . ? C15 C12 C11 107.39(9) . . ? C15 C12 C13 111.59(9) . . ? C11 C12 C13 113.31(9) . . ? O2 C13 C1 105.92(9) . . ? O2 C13 C12 110.48(9) . . ? C1 C13 C12 110.80(9) . . ? O2 C13 C14 109.21(9) . . ? C1 C13 C14 108.99(9) . . ? C12 C13 C14 111.29(9) . . ? C13 C14 Cl2 112.24(8) . . ? C13 C14 Cl1 111.72(8) . . ? Cl2 C14 Cl1 109.51(6) . . ? O3 C15 O4 124.56(11) . . ? O3 C15 C12 123.03(10) . . ? O4 C15 C12 112.41(9) . . ? C15 O4 C16 115.21(10) . . ? C8 O6 C9 114.97(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.395 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.045 # Attachment 'ks1145.cif' # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items data_ks1145 _database_code_depnum_ccdc_archive 'CCDC 832479' #TrackingRef 'ks1145.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 O8' _chemical_formula_weight 362.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 8.2989(6) _cell_length_b 10.1312(7) _cell_length_c 10.4773(7) _cell_angle_alpha 86.560(5) _cell_angle_beta 83.809(5) _cell_angle_gamma 70.127(5) _cell_volume 823.36(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5672 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 28.40 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.116 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13589 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.91 _reflns_number_total 3926 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0851P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3926 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.21725(15) 0.60148(12) 0.16701(12) 0.0185(2) Uani 1 1 d . . . H1 H 0.2825 0.6687 0.1610 0.022 Uiso 1 1 calc R . . C2 C 0.34496(15) 0.45305(13) 0.16889(12) 0.0204(3) Uani 1 1 d . . . C3 C 0.37666(16) 0.37548(13) 0.04888(12) 0.0220(3) Uani 1 1 d . . . C4 C 0.47917(18) 0.23377(14) 0.04460(14) 0.0287(3) Uani 1 1 d . . . H4 H 0.5239 0.1861 0.1207 0.034 Uiso 1 1 calc R . . C5 C 0.51593(18) 0.16263(15) -0.06839(15) 0.0314(3) Uani 1 1 d . . . H5B H 0.5835 0.0658 -0.0702 0.038 Uiso 1 1 calc R . . C6 C 0.45311(18) 0.23385(16) -0.18027(15) 0.0302(3) Uani 1 1 d . . . H6 H 0.4793 0.1849 -0.2585 0.036 Uiso 1 1 calc R . . C7 C 0.35362(17) 0.37409(15) -0.17959(14) 0.0274(3) Uani 1 1 d . . . H7 H 0.3132 0.4220 -0.2568 0.033 Uiso 1 1 calc R . . C8 C 0.31336(15) 0.44436(14) -0.06416(13) 0.0223(3) Uani 1 1 d . . . C9 C 0.11114(16) 0.62845(13) 0.05251(12) 0.0216(3) Uani 1 1 d . . . H9 H 0.0258 0.5780 0.0677 0.026 Uiso 1 1 calc R . . C10 C 0.01599(18) 0.78343(14) 0.03701(14) 0.0289(3) Uani 1 1 d . . . H10A H 0.0979 0.8312 0.0020 0.035 Uiso 1 1 calc R . . H10B H -0.0711 0.7986 -0.0249 0.035 Uiso 1 1 calc R . . C11 C -0.07051(17) 0.84521(13) 0.16194(14) 0.0259(3) Uani 1 1 d . . . C12 C -0.04113(16) 0.77843(13) 0.27813(13) 0.0225(3) Uani 1 1 d . . . C13 C 0.09156(15) 0.63140(12) 0.29022(12) 0.0196(2) Uani 1 1 d . . . C14 C 0.19242(15) 0.61778(13) 0.40859(12) 0.0201(2) Uani 1 1 d . . . C15 C -0.15104(17) 0.84623(14) 0.38989(14) 0.0270(3) Uani 1 1 d . . . C16 C -0.2224(2) 0.82743(17) 0.61571(16) 0.0437(4) Uani 1 1 d . . . H16A H -0.2392 0.7516 0.6739 0.052 Uiso 1 1 calc R . . H16B H -0.3371 0.8932 0.5974 0.052 Uiso 1 1 calc R . . C17 C -0.1279(3) 0.9038(3) 0.6795(2) 0.0644(6) Uani 1 1 d . . . H17A H -0.0138 0.8388 0.6965 0.097 Uiso 1 1 calc R . . H17B H -0.1928 0.9415 0.7607 0.097 Uiso 1 1 calc R . . H17C H -0.1153 0.9811 0.6231 0.097 Uiso 1 1 calc R . . C18 C 0.37166(19) 0.70856(15) 0.50882(14) 0.0302(3) Uani 1 1 d . . . H18A H 0.3049 0.7010 0.5903 0.045 Uiso 1 1 calc R . . H18B H 0.4012 0.7945 0.5071 0.045 Uiso 1 1 calc R . . H18C H 0.4774 0.6269 0.5005 0.045 Uiso 1 1 calc R . . O1 O 0.42053(12) 0.40396(10) 0.26296(9) 0.0281(2) Uani 1 1 d . . . O2 O 0.01559(12) 0.52511(9) 0.29888(10) 0.0228(2) Uani 1 1 d . . . O3 O -0.26016(14) 0.96437(11) 0.38700(11) 0.0392(3) Uani 1 1 d . . . O4 O -0.12497(13) 0.76755(10) 0.49613(10) 0.0325(2) Uani 1 1 d . . . O5 O -0.18532(14) 0.97349(11) 0.14785(12) 0.0353(3) Uani 1 1 d . . . O6 O 0.21465(11) 0.58321(10) -0.06595(9) 0.0253(2) Uani 1 1 d . . . O7 O 0.19746(12) 0.53305(10) 0.49477(9) 0.0257(2) Uani 1 1 d . . . O8 O 0.27015(12) 0.71350(9) 0.40313(9) 0.0243(2) Uani 1 1 d . . . H2 H -0.029(3) 0.521(2) 0.372(2) 0.054(6) Uiso 1 1 d . . . H5A H -0.232(3) 0.997(2) 0.231(2) 0.066(7) Uiso 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 0.0169(5) 0.0188(6) 0.0201(6) 0.0001(5) -0.0031(4) -0.0061(4) C2 0.0170(5) 0.0219(6) 0.0220(6) 0.0018(5) -0.0010(5) -0.0069(5) C3 0.0187(5) 0.0227(6) 0.0245(6) -0.0008(5) 0.0001(5) -0.0076(5) C4 0.0277(7) 0.0245(6) 0.0308(7) 0.0020(5) 0.0019(5) -0.0066(5) C5 0.0303(7) 0.0228(6) 0.0391(8) -0.0057(6) 0.0078(6) -0.0090(6) C6 0.0268(7) 0.0355(7) 0.0324(7) -0.0127(6) 0.0057(6) -0.0162(6) C7 0.0217(6) 0.0380(7) 0.0261(7) -0.0051(6) -0.0017(5) -0.0139(6) C8 0.0170(5) 0.0252(6) 0.0262(6) -0.0009(5) -0.0022(5) -0.0089(5) C9 0.0193(6) 0.0232(6) 0.0212(6) -0.0006(5) -0.0041(5) -0.0053(5) C10 0.0306(7) 0.0249(7) 0.0266(7) 0.0037(5) -0.0092(5) -0.0020(5) C11 0.0226(6) 0.0187(6) 0.0359(7) -0.0008(5) -0.0077(5) -0.0047(5) C12 0.0195(6) 0.0186(6) 0.0291(7) -0.0024(5) -0.0042(5) -0.0051(5) C13 0.0185(5) 0.0181(6) 0.0231(6) 0.0002(5) -0.0029(5) -0.0069(5) C14 0.0171(5) 0.0196(6) 0.0214(6) -0.0032(5) 0.0010(4) -0.0036(5) C15 0.0226(6) 0.0218(6) 0.0362(8) -0.0039(5) -0.0012(5) -0.0068(5) C16 0.0505(10) 0.0290(8) 0.0394(9) -0.0044(7) 0.0222(8) -0.0051(7) C17 0.0634(13) 0.0800(15) 0.0373(10) -0.0205(10) -0.0018(9) -0.0057(11) C18 0.0324(7) 0.0305(7) 0.0304(7) -0.0041(6) -0.0120(6) -0.0106(6) O1 0.0252(5) 0.0296(5) 0.0242(5) 0.0025(4) -0.0057(4) -0.0017(4) O2 0.0231(4) 0.0227(4) 0.0251(5) -0.0008(4) 0.0000(4) -0.0116(4) O3 0.0357(6) 0.0248(5) 0.0474(7) -0.0065(5) -0.0002(5) 0.0022(4) O4 0.0358(5) 0.0235(5) 0.0317(5) -0.0028(4) 0.0089(4) -0.0048(4) O5 0.0350(5) 0.0219(5) 0.0409(6) 0.0025(4) -0.0094(5) 0.0021(4) O6 0.0251(5) 0.0270(5) 0.0206(5) 0.0010(4) -0.0035(4) -0.0044(4) O7 0.0260(5) 0.0274(5) 0.0220(5) 0.0034(4) -0.0010(4) -0.0078(4) O8 0.0270(4) 0.0241(4) 0.0252(5) 0.0002(4) -0.0077(4) -0.0114(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5173(16) . ? C1 C9 1.5213(17) . ? C1 C13 1.5453(17) . ? C2 O1 1.2143(15) . ? C2 C3 1.4746(18) . ? C3 C8 1.3969(18) . ? C3 C4 1.3986(18) . ? C4 C5 1.374(2) . ? C5 C6 1.393(2) . ? C6 C7 1.379(2) . ? C7 C8 1.3912(19) . ? C8 O6 1.3664(16) . ? C9 O6 1.4349(15) . ? C9 C10 1.5065(17) . ? C10 C11 1.487(2) . ? C11 O5 1.3358(16) . ? C11 C12 1.3609(19) . ? C12 C15 1.4544(19) . ? C12 C13 1.5296(17) . ? C13 O2 1.4153(14) . ? C13 C14 1.5435(18) . ? C14 O7 1.2019(15) . ? C14 O8 1.3306(15) . ? C15 O3 1.2322(16) . ? C15 O4 1.3227(17) . ? C16 O4 1.4596(18) . ? C16 C17 1.500(3) . ? C18 O8 1.4506(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 111.60(10) . . ? C2 C1 C13 111.63(9) . . ? C9 C1 C13 107.92(10) . . ? O1 C2 C3 122.48(11) . . ? O1 C2 C1 121.28(12) . . ? C3 C2 C1 116.19(10) . . ? C8 C3 C4 118.88(12) . . ? C8 C3 C2 120.52(11) . . ? C4 C3 C2 120.49(12) . . ? C5 C4 C3 120.79(13) . . ? C4 C5 C6 119.35(13) . . ? C7 C6 C5 121.26(13) . . ? C6 C7 C8 119.00(13) . . ? O6 C8 C7 117.90(12) . . ? O6 C8 C3 121.37(12) . . ? C7 C8 C3 120.70(12) . . ? O6 C9 C10 107.13(10) . . ? O6 C9 C1 112.74(10) . . ? C10 C9 C1 109.84(11) . . ? C11 C10 C9 111.04(11) . . ? O5 C11 C12 123.09(13) . . ? O5 C11 C10 112.43(12) . . ? C12 C11 C10 124.45(12) . . ? C11 C12 C15 117.66(11) . . ? C11 C12 C13 121.50(12) . . ? C15 C12 C13 120.62(11) . . ? O2 C13 C12 112.35(10) . . ? O2 C13 C14 108.70(10) . . ? C12 C13 C14 111.26(10) . . ? O2 C13 C1 105.53(10) . . ? C12 C13 C1 108.99(10) . . ? C14 C13 C1 109.86(9) . . ? O7 C14 O8 124.84(12) . . ? O7 C14 C13 124.20(11) . . ? O8 C14 C13 110.95(10) . . ? O3 C15 O4 122.61(13) . . ? O3 C15 C12 123.98(13) . . ? O4 C15 C12 113.40(11) . . ? O4 C16 C17 110.11(14) . . ? C15 O4 C16 118.21(11) . . ? C8 O6 C9 113.54(9) . . ? C14 O8 C18 115.62(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.335 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.040 # Attachment 'ks1186.cif' # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Data block identification for start of deposition data_ks1186 _database_code_depnum_ccdc_archive 'CCDC 832480' #TrackingRef 'ks1186.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 O7' _chemical_formula_weight 434.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.152(2) _cell_length_b 8.2423(16) _cell_length_c 12.511(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.49(3) _cell_angle_gamma 90.00 _cell_volume 1032.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7185 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 29.65 _exptl_crystal_description prism _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.102 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17051 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2532 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2532 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 1.09553(17) 0.6565(2) 1.23809(14) 0.0256(4) Uani 1 1 d . . . C2 C 1.0267(2) 0.6117(3) 1.32095(16) 0.0328(4) Uani 1 1 d . . . H2 H 1.0605 0.6414 1.3937 0.039 Uiso 1 1 calc R . . C3 C 0.9105(2) 0.5251(3) 1.29789(17) 0.0354(4) Uani 1 1 d . . . H3 H 0.8644 0.4955 1.3551 0.042 Uiso 1 1 calc R . . C4 C 0.85851(18) 0.4797(2) 1.19231(17) 0.0325(4) Uani 1 1 d . . . H4 H 0.7774 0.4202 1.1774 0.039 Uiso 1 1 calc R . . C5 C 0.92606(16) 0.5219(2) 1.10960(15) 0.0251(4) Uani 1 1 d . . . H5 H 0.8913 0.4902 1.0375 0.030 Uiso 1 1 calc R . . C6 C 1.04581(16) 0.6113(2) 1.13014(14) 0.0218(3) Uani 1 1 d . . . C7 C 1.12557(15) 0.6464(2) 1.04532(13) 0.0215(3) Uani 1 1 d . . . C8 C 1.08425(16) 0.5949(2) 0.93019(14) 0.0210(3) Uani 1 1 d . . . C9 C 1.17652(16) 0.5143(2) 0.87867(13) 0.0202(3) Uani 1 1 d . . . C10 C 1.14616(16) 0.4797(2) 0.76752(14) 0.0223(3) Uani 1 1 d . . . C11 C 1.02383(17) 0.5334(2) 0.70878(14) 0.0241(3) Uani 1 1 d . . . C12 C 0.92959(16) 0.6149(2) 0.76004(14) 0.0236(3) Uani 1 1 d . . . C13 C 0.96109(16) 0.6425(2) 0.86981(14) 0.0231(3) Uani 1 1 d . . . H13 H 0.8977 0.6954 0.9058 0.028 Uiso 1 1 calc R . . C14 C 1.30300(16) 0.4559(2) 0.94801(14) 0.0213(3) Uani 1 1 d . . . C15 C 1.53374(17) 0.4878(3) 0.99858(18) 0.0368(5) Uani 1 1 d . . . H15A H 1.5588 0.3827 0.9712 0.055 Uiso 1 1 calc R . . H15B H 1.5222 0.4764 1.0745 0.055 Uiso 1 1 calc R . . H15C H 1.6042 0.5673 0.9934 0.055 Uiso 1 1 calc R . . C16 C 1.23478(17) 0.3836(2) 0.70822(14) 0.0237(3) Uani 1 1 d . . . C17 C 1.42809(19) 0.2216(3) 0.71861(18) 0.0358(4) Uani 1 1 d . . . H17A H 1.4602 0.2881 0.6633 0.054 Uiso 1 1 calc R . . H17B H 1.3814 0.1261 0.6844 0.054 Uiso 1 1 calc R . . H17C H 1.5041 0.1866 0.7724 0.054 Uiso 1 1 calc R . . C18 C 0.79978(17) 0.6650(3) 0.69137(15) 0.0295(4) Uani 1 1 d . . . H18A H 0.7514 0.5660 0.6623 0.035 Uiso 1 1 calc R . . H18B H 0.8202 0.7285 0.6289 0.035 Uiso 1 1 calc R . . C19 C 0.70811(16) 0.7649(2) 0.74965(14) 0.0272(4) Uani 1 1 d . . . H19A H 0.6881 0.7036 0.8131 0.033 Uiso 1 1 calc R . . H19B H 0.7539 0.8667 0.7764 0.033 Uiso 1 1 calc R . . C20 C 0.57890(16) 0.8053(2) 0.67568(13) 0.0233(3) Uani 1 1 d . . . C21 C 0.57738(18) 0.9085(2) 0.58810(15) 0.0275(4) Uani 1 1 d . . . H21 H 0.6579 0.9591 0.5766 0.033 Uiso 1 1 calc R . . C22 C 0.46015(18) 0.9390(2) 0.51701(15) 0.0298(4) Uani 1 1 d . . . H22 H 0.4607 1.0103 0.4574 0.036 Uiso 1 1 calc R . . C23 C 0.34235(18) 0.8656(2) 0.53291(15) 0.0292(4) Uani 1 1 d . . . H23 H 0.2621 0.8845 0.4836 0.035 Uiso 1 1 calc R . . C24 C 0.34218(17) 0.7650(2) 0.62073(16) 0.0296(4) Uani 1 1 d . . . H24 H 0.2613 0.7155 0.6325 0.036 Uiso 1 1 calc R . . C25 C 0.45962(17) 0.7354(2) 0.69230(15) 0.0274(4) Uani 1 1 d . . . H25 H 0.4582 0.6668 0.7531 0.033 Uiso 1 1 calc R . . O1 O 1.20987(13) 0.73981(18) 1.26566(11) 0.0335(3) Uani 1 1 d . . . O2 O 1.23389(11) 0.71742(17) 1.06782(10) 0.0299(3) Uani 1 1 d . . . O3 O 1.30277(12) 0.34531(16) 1.01026(10) 0.0303(3) Uani 1 1 d . . . O4 O 1.40961(11) 0.54225(15) 0.93453(10) 0.0260(3) Uani 1 1 d . . . O5 O 1.21487(13) 0.36713(18) 0.61022(10) 0.0330(3) Uani 1 1 d . . . O6 O 1.33696(12) 0.31633(16) 0.77160(10) 0.0284(3) Uani 1 1 d . . . O7 O 0.99020(13) 0.50870(18) 0.60131(10) 0.0324(3) Uani 1 1 d . . . H1 H 1.242(2) 0.746(3) 1.208(2) 0.033(6) Uiso 1 1 d . . . H7 H 1.058(3) 0.452(3) 0.581(2) 0.049(7) Uiso 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 0.0278(8) 0.0261(8) 0.0227(9) -0.0014(7) 0.0036(7) 0.0051(7) C2 0.0407(10) 0.0364(10) 0.0222(9) -0.0016(8) 0.0078(8) 0.0053(8) C3 0.0384(10) 0.0373(10) 0.0351(11) 0.0055(9) 0.0194(8) 0.0057(9) C4 0.0251(9) 0.0324(9) 0.0415(12) 0.0046(8) 0.0097(8) 0.0013(7) C5 0.0231(8) 0.0260(8) 0.0255(9) 0.0001(7) 0.0023(6) 0.0018(7) C6 0.0200(7) 0.0225(7) 0.0227(9) 0.0001(7) 0.0036(6) 0.0057(6) C7 0.0203(7) 0.0228(8) 0.0204(8) -0.0001(7) 0.0006(6) 0.0038(6) C8 0.0210(7) 0.0229(8) 0.0186(8) 0.0003(6) 0.0024(6) -0.0013(6) C9 0.0194(7) 0.0199(8) 0.0215(8) 0.0024(7) 0.0036(6) -0.0023(6) C10 0.0238(8) 0.0222(8) 0.0217(8) -0.0003(6) 0.0064(6) -0.0011(6) C11 0.0272(8) 0.0261(8) 0.0189(8) -0.0008(7) 0.0034(6) -0.0018(7) C12 0.0209(8) 0.0253(8) 0.0229(9) -0.0011(7) -0.0010(6) 0.0008(6) C13 0.0221(7) 0.0249(8) 0.0222(8) -0.0022(7) 0.0032(6) 0.0012(7) C14 0.0221(8) 0.0229(8) 0.0193(8) -0.0002(6) 0.0048(6) 0.0017(6) C15 0.0210(9) 0.0401(11) 0.0466(12) -0.0004(9) -0.0021(8) 0.0026(8) C16 0.0237(8) 0.0237(8) 0.0249(9) -0.0017(7) 0.0076(7) -0.0037(6) C17 0.0314(9) 0.0380(11) 0.0410(11) -0.0041(9) 0.0151(8) 0.0086(8) C18 0.0260(8) 0.0375(10) 0.0225(9) -0.0046(8) -0.0035(7) 0.0085(7) C19 0.0252(8) 0.0336(9) 0.0212(9) -0.0038(7) -0.0010(7) 0.0038(7) C20 0.0238(8) 0.0262(8) 0.0196(8) -0.0045(7) 0.0027(6) 0.0056(7) C21 0.0240(8) 0.0297(9) 0.0300(10) 0.0023(7) 0.0078(7) 0.0011(7) C22 0.0321(9) 0.0368(10) 0.0215(9) 0.0070(8) 0.0070(7) 0.0081(8) C23 0.0260(8) 0.0338(10) 0.0257(9) -0.0014(8) -0.0017(7) 0.0064(7) C24 0.0229(8) 0.0293(9) 0.0367(11) 0.0034(8) 0.0054(7) -0.0008(7) C25 0.0302(8) 0.0279(9) 0.0248(9) 0.0054(7) 0.0069(7) 0.0037(7) O1 0.0331(7) 0.0449(8) 0.0212(7) -0.0070(6) 0.0004(5) -0.0061(6) O2 0.0233(6) 0.0412(7) 0.0250(7) -0.0061(6) 0.0034(5) -0.0075(5) O3 0.0300(6) 0.0335(7) 0.0285(7) 0.0101(6) 0.0077(5) 0.0046(5) O4 0.0201(5) 0.0273(6) 0.0300(7) 0.0013(5) 0.0028(5) 0.0000(5) O5 0.0346(7) 0.0423(8) 0.0234(7) -0.0045(6) 0.0089(5) 0.0036(6) O6 0.0269(6) 0.0312(6) 0.0282(7) -0.0034(6) 0.0079(5) 0.0061(5) O7 0.0320(6) 0.0455(8) 0.0185(6) -0.0048(6) 0.0009(5) 0.0071(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.344(2) . ? C1 C2 1.392(3) . ? C1 C6 1.412(2) . ? C2 C3 1.369(3) . ? C3 C4 1.391(3) . ? C4 C5 1.377(3) . ? C5 C6 1.408(2) . ? C6 C7 1.466(2) . ? C7 O2 1.237(2) . ? C7 C8 1.494(2) . ? C8 C9 1.390(2) . ? C8 C13 1.406(2) . ? C9 C10 1.403(2) . ? C9 C14 1.505(2) . ? C10 C11 1.406(2) . ? C10 C16 1.486(2) . ? C11 O7 1.347(2) . ? C11 C12 1.407(2) . ? C12 C13 1.377(2) . ? C12 C18 1.507(2) . ? C14 O3 1.199(2) . ? C14 O4 1.329(2) . ? C15 O4 1.449(2) . ? C16 O5 1.217(2) . ? C16 O6 1.320(2) . ? C17 O6 1.452(2) . ? C18 C19 1.516(2) . ? C19 C20 1.512(2) . ? C20 C21 1.385(3) . ? C20 C25 1.387(2) . ? C21 C22 1.386(3) . ? C22 C23 1.383(3) . ? C23 C24 1.377(3) . ? C24 C25 1.389(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 O1 C1 C2 117.56(17) . . ? O1 C1 C6 122.55(16) . . ? C2 C1 C6 119.88(17) . . ? C3 C2 C1 120.16(19) . . ? C2 C3 C4 121.31(17) . . ? C5 C4 C3 119.20(18) . . ? C4 C5 C6 121.13(17) . . ? C5 C6 C1 118.32(15) . . ? C5 C6 C7 122.31(16) . . ? C1 C6 C7 119.16(15) . . ? O2 C7 C6 120.35(15) . . ? O2 C7 C8 116.86(15) . . ? C6 C7 C8 122.75(15) . . ? C9 C8 C13 119.46(15) . . ? C9 C8 C7 118.64(14) . . ? C13 C8 C7 121.47(15) . . ? C8 C9 C10 120.13(15) . . ? C8 C9 C14 117.48(15) . . ? C10 C9 C14 122.22(14) . . ? C9 C10 C11 118.99(15) . . ? C9 C10 C16 123.45(15) . . ? C11 C10 C16 117.53(15) . . ? O7 C11 C10 122.05(15) . . ? O7 C11 C12 116.59(15) . . ? C10 C11 C12 121.35(15) . . ? C13 C12 C11 118.03(15) . . ? C13 C12 C18 124.11(15) . . ? C11 C12 C18 117.85(15) . . ? C12 C13 C8 121.97(15) . . ? O3 C14 O4 125.33(16) . . ? O3 C14 C9 121.66(15) . . ? O4 C14 C9 112.98(14) . . ? O5 C16 O6 122.82(16) . . ? O5 C16 C10 123.30(17) . . ? O6 C16 C10 113.88(15) . . ? C12 C18 C19 115.02(15) . . ? C20 C19 C18 111.37(14) . . ? C21 C20 C25 118.51(16) . . ? C21 C20 C19 120.97(16) . . ? C25 C20 C19 120.50(16) . . ? C20 C21 C22 121.03(17) . . ? C23 C22 C21 119.95(17) . . ? C24 C23 C22 119.53(16) . . ? C23 C24 C25 120.41(16) . . ? C20 C25 C24 120.53(16) . . ? C14 O4 C15 114.58(14) . . ? C16 O6 C17 116.66(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.218 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.031 # Attachment 'ks1189.cif' # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Data block identification for start of deposition data_ks1189 _database_code_depnum_ccdc_archive 'CCDC 832481' #TrackingRef 'ks1189.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 O8' _chemical_formula_weight 424.39 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 7.9176(4) _cell_length_b 11.1261(6) _cell_length_c 11.5814(7) _cell_angle_alpha 89.052(5) _cell_angle_beta 80.895(4) _cell_angle_gamma 77.206(4) _cell_volume 982.18(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5183 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 29.65 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8339 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details 'X-SHAPE and X-RED32 (Stoe & Cie, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16353 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4524 _reflns_number_gt 3102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4524 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _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 0.23877(16) -0.06932(12) 0.53009(11) 0.0256(3) Uani 1 1 d . . . C2 C 0.24694(17) -0.13355(13) 0.63410(12) 0.0295(3) Uani 1 1 d . . . H2 H 0.2499 -0.0922 0.7046 0.035 Uiso 1 1 calc R . . C3 C 0.25060(18) -0.25783(13) 0.63310(13) 0.0344(3) Uani 1 1 d . . . H3B H 0.2558 -0.3019 0.7038 0.041 Uiso 1 1 calc R . . C4 C 0.24682(19) -0.32008(13) 0.53093(13) 0.0362(3) Uani 1 1 d . . . H4 H 0.2523 -0.4063 0.5313 0.043 Uiso 1 1 calc R . . C5 C 0.23498(19) -0.25525(12) 0.42892(13) 0.0321(3) Uani 1 1 d . . . H5 H 0.2302 -0.2970 0.3590 0.039 Uiso 1 1 calc R . . C6 C 0.22996(17) -0.12889(12) 0.42713(11) 0.0256(3) Uani 1 1 d . . . C7 C 0.20164(17) -0.05685(11) 0.32077(11) 0.0246(3) Uani 1 1 d . . . C8 C 0.21943(16) 0.07563(11) 0.32465(10) 0.0220(3) Uani 1 1 d . . . H8B H 0.0989 0.1299 0.3362 0.026 Uiso 1 1 calc R . . C9 C 0.32205(16) 0.11241(11) 0.20956(10) 0.0213(3) Uani 1 1 d . . . C10 C 0.34718(16) 0.24324(11) 0.22305(11) 0.0227(3) Uani 1 1 d . . . C11 C 0.33034(17) 0.29764(11) 0.32938(11) 0.0248(3) Uani 1 1 d . . . C12 C 0.28781(19) 0.23698(12) 0.44294(11) 0.0277(3) Uani 1 1 d . . . H12A H 0.1654 0.2734 0.4787 0.033 Uiso 1 1 calc R . . H12B H 0.3661 0.2521 0.4972 0.033 Uiso 1 1 calc R . . C13 C 0.30971(17) 0.10033(11) 0.42546(10) 0.0234(3) Uani 1 1 d . . . H13 H 0.4375 0.0608 0.4073 0.028 Uiso 1 1 calc R . . C14 C 0.22049(17) 0.10229(11) 0.10798(11) 0.0222(3) Uani 1 1 d . . . C15 C -0.0467(2) 0.17844(14) 0.03772(13) 0.0362(3) Uani 1 1 d . . . H15A H 0.0208 0.1845 -0.0399 0.054 Uiso 1 1 calc R . . H15B H -0.1476 0.2486 0.0513 0.054 Uiso 1 1 calc R . . H15C H -0.0881 0.1015 0.0421 0.054 Uiso 1 1 calc R . . C16 C 0.40715(16) 0.30899(11) 0.12060(11) 0.0246(3) Uani 1 1 d . . . C17 C 0.49379(18) 0.30035(12) -0.08766(11) 0.0293(3) Uani 1 1 d . . . H17A H 0.5832 0.2411 -0.1406 0.035 Uiso 1 1 calc R . . H17B H 0.5440 0.3716 -0.0731 0.035 Uiso 1 1 calc R . . C18 C 0.33258(18) 0.34273(11) -0.14320(11) 0.0267(3) Uani 1 1 d . . . C19 C 0.28044(19) 0.26193(12) -0.21306(11) 0.0308(3) Uani 1 1 d . . . H19 H 0.3506 0.1811 -0.2287 0.037 Uiso 1 1 calc R . . C20 C 0.1277(2) 0.29785(13) -0.26000(12) 0.0349(3) Uani 1 1 d . . . H20 H 0.0918 0.2415 -0.3065 0.042 Uiso 1 1 calc R . . C21 C 0.0273(2) 0.41592(14) -0.23917(14) 0.0389(3) Uani 1 1 d . . . H21 H -0.0770 0.4413 -0.2723 0.047 Uiso 1 1 calc R . . C22 C 0.0782(2) 0.49720(13) -0.17040(15) 0.0429(4) Uani 1 1 d . . . H22 H 0.0090 0.5785 -0.1562 0.051 Uiso 1 1 calc R . . C23 C 0.2296(2) 0.46059(12) -0.12215(13) 0.0352(3) Uani 1 1 d . . . H23 H 0.2634 0.5166 -0.0741 0.042 Uiso 1 1 calc R . . O1 O 0.23544(12) 0.05393(8) 0.53415(7) 0.0275(2) Uani 1 1 d . . . O2 O 0.15871(13) -0.09884(8) 0.23664(8) 0.0319(2) Uani 1 1 d . . . O3 O 0.48494(12) 0.02602(8) 0.18936(8) 0.0245(2) Uani 1 1 d . . . O4 O 0.27703(12) 0.03504(8) 0.02438(8) 0.0273(2) Uani 1 1 d . . . O5 O 0.06396(12) 0.17959(8) 0.12610(8) 0.0263(2) Uani 1 1 d . . . O6 O 0.42357(14) 0.41632(8) 0.12367(8) 0.0348(2) Uani 1 1 d . . . O7 O 0.44612(12) 0.24105(8) 0.02334(7) 0.0276(2) Uani 1 1 d . . . O8 O 0.35324(13) 0.41141(8) 0.34458(9) 0.0318(2) Uani 1 1 d . . . H3A H 0.526(2) 0.0219(15) 0.1189(16) 0.045(5) Uiso 1 1 d . . . H8A H 0.381(2) 0.4376(17) 0.2687(17) 0.060(6) Uiso 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 0.0162(6) 0.0293(7) 0.0300(7) 0.0046(5) -0.0015(5) -0.0040(5) C2 0.0207(7) 0.0397(8) 0.0275(7) 0.0061(6) -0.0024(5) -0.0069(6) C3 0.0244(7) 0.0405(8) 0.0372(8) 0.0165(6) -0.0046(6) -0.0061(6) C4 0.0327(8) 0.0287(7) 0.0479(9) 0.0113(6) -0.0072(7) -0.0088(6) C5 0.0303(8) 0.0298(7) 0.0377(8) 0.0033(6) -0.0063(6) -0.0090(6) C6 0.0208(7) 0.0272(6) 0.0293(7) 0.0051(5) -0.0036(5) -0.0069(5) C7 0.0208(6) 0.0263(6) 0.0269(7) 0.0007(5) -0.0011(5) -0.0073(5) C8 0.0195(6) 0.0220(6) 0.0237(6) 0.0014(5) -0.0027(5) -0.0033(5) C9 0.0192(6) 0.0200(6) 0.0239(6) 0.0021(5) -0.0035(5) -0.0031(5) C10 0.0195(6) 0.0201(6) 0.0288(7) 0.0021(5) -0.0068(5) -0.0035(5) C11 0.0210(7) 0.0200(6) 0.0336(7) -0.0002(5) -0.0072(5) -0.0031(5) C12 0.0298(7) 0.0270(6) 0.0260(6) -0.0030(5) -0.0043(5) -0.0055(5) C13 0.0222(7) 0.0255(6) 0.0226(6) 0.0019(5) -0.0024(5) -0.0060(5) C14 0.0234(6) 0.0194(6) 0.0247(6) 0.0034(5) -0.0024(5) -0.0079(5) C15 0.0318(8) 0.0390(8) 0.0393(8) -0.0031(6) -0.0177(7) -0.0020(6) C16 0.0201(6) 0.0230(6) 0.0318(7) 0.0033(5) -0.0080(5) -0.0045(5) C17 0.0302(7) 0.0290(7) 0.0277(7) 0.0073(5) -0.0011(6) -0.0078(6) C18 0.0283(7) 0.0247(6) 0.0255(7) 0.0064(5) -0.0003(5) -0.0059(5) C19 0.0373(8) 0.0230(6) 0.0283(7) 0.0001(5) -0.0027(6) -0.0006(6) C20 0.0418(9) 0.0341(7) 0.0301(7) -0.0032(6) -0.0079(6) -0.0090(6) C21 0.0341(8) 0.0372(8) 0.0456(9) 0.0030(7) -0.0145(7) -0.0025(6) C22 0.0391(9) 0.0246(7) 0.0633(11) -0.0027(7) -0.0149(8) 0.0014(6) C23 0.0368(8) 0.0240(7) 0.0459(9) -0.0035(6) -0.0100(7) -0.0065(6) O1 0.0306(5) 0.0284(5) 0.0227(5) 0.0012(4) -0.0014(4) -0.0070(4) O2 0.0395(6) 0.0309(5) 0.0297(5) 0.0020(4) -0.0079(4) -0.0155(4) O3 0.0212(5) 0.0243(5) 0.0251(5) 0.0020(4) -0.0018(4) -0.0003(4) O4 0.0295(5) 0.0269(5) 0.0257(5) -0.0035(4) -0.0019(4) -0.0081(4) O5 0.0241(5) 0.0254(4) 0.0294(5) -0.0019(4) -0.0100(4) -0.0014(4) O6 0.0449(6) 0.0243(5) 0.0383(6) 0.0046(4) -0.0073(5) -0.0141(4) O7 0.0325(5) 0.0245(4) 0.0263(5) 0.0051(4) -0.0040(4) -0.0081(4) O8 0.0395(6) 0.0216(5) 0.0361(6) -0.0021(4) -0.0096(5) -0.0078(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.3671(15) . ? C1 C6 1.3925(18) . ? C1 C2 1.3934(18) . ? C2 C3 1.377(2) . ? C3 C4 1.389(2) . ? C4 C5 1.3790(19) . ? C5 C6 1.3975(18) . ? C6 C7 1.4782(17) . ? C7 O2 1.2138(15) . ? C7 C8 1.5135(16) . ? C8 C13 1.5203(17) . ? C8 C9 1.5462(16) . ? C9 O3 1.4160(15) . ? C9 C10 1.5259(16) . ? C9 C14 1.5450(17) . ? C10 C11 1.3556(18) . ? C10 C16 1.4543(17) . ? C11 O8 1.3361(15) . ? C11 C12 1.4932(18) . ? C12 C13 1.5050(17) . ? C13 O1 1.4407(14) . ? C14 O4 1.1984(15) . ? C14 O5 1.3309(15) . ? C15 O5 1.4508(15) . ? C16 O6 1.2312(15) . ? C16 O7 1.3230(15) . ? C17 O7 1.4694(14) . ? C17 C18 1.4995(19) . ? C18 C23 1.3849(19) . ? C18 C19 1.3883(18) . ? C19 C20 1.380(2) . ? C20 C21 1.379(2) . ? C21 C22 1.379(2) . ? C22 C23 1.379(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 121.81(11) . . ? O1 C1 C2 117.48(12) . . ? C6 C1 C2 120.69(12) . . ? C3 C2 C1 118.98(13) . . ? C2 C3 C4 121.44(12) . . ? C5 C4 C3 119.16(13) . . ? C4 C5 C6 120.80(14) . . ? C1 C6 C5 118.88(12) . . ? C1 C6 C7 119.94(11) . . ? C5 C6 C7 121.00(12) . . ? O2 C7 C6 122.43(11) . . ? O2 C7 C8 121.29(11) . . ? C6 C7 C8 116.20(11) . . ? C7 C8 C13 111.95(10) . . ? C7 C8 C9 112.08(10) . . ? C13 C8 C9 108.54(10) . . ? O3 C9 C10 111.42(10) . . ? O3 C9 C14 108.83(10) . . ? C10 C9 C14 111.33(9) . . ? O3 C9 C8 106.66(9) . . ? C10 C9 C8 109.20(10) . . ? C14 C9 C8 109.27(9) . . ? C11 C10 C16 117.79(11) . . ? C11 C10 C9 122.03(11) . . ? C16 C10 C9 119.92(11) . . ? O8 C11 C10 123.69(11) . . ? O8 C11 C12 112.12(11) . . ? C10 C11 C12 124.17(11) . . ? C11 C12 C13 110.99(11) . . ? O1 C13 C12 106.88(10) . . ? O1 C13 C8 111.97(10) . . ? C12 C13 C8 109.97(10) . . ? O4 C14 O5 125.34(12) . . ? O4 C14 C9 124.24(12) . . ? O5 C14 C9 110.42(10) . . ? O6 C16 O7 122.98(11) . . ? O6 C16 C10 123.76(12) . . ? O7 C16 C10 113.24(10) . . ? O7 C17 C18 108.89(10) . . ? C23 C18 C19 118.92(13) . . ? C23 C18 C17 120.96(12) . . ? C19 C18 C17 120.07(12) . . ? C20 C19 C18 120.67(13) . . ? C21 C20 C19 119.74(13) . . ? C22 C21 C20 120.11(14) . . ? C21 C22 C23 120.07(14) . . ? C22 C23 C18 120.48(13) . . ? C1 O1 C13 113.65(9) . . ? C14 O5 C15 116.24(10) . . ? C16 O7 C17 118.30(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.295 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.036 # Attachment 'ks1245.cif' # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Data block identification for start of deposition data_ks1245 _database_code_depnum_ccdc_archive 'CCDC 832482' #TrackingRef 'ks1245.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Cl O7' _chemical_formula_weight 406.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.7224(3) _cell_length_b 8.1879(2) _cell_length_c 23.1457(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.519(3) _cell_angle_gamma 90.00 _cell_volume 1834.00(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6857 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 28.37 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8322 _exptl_absorpt_correction_T_max 0.9655 _exptl_absorpt_process_details 'X-SHAPE and X-RED32 (Stoe & Cie, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30879 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.91 _reflns_number_total 4380 _reflns_number_gt 3277 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4380 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 0.76816(12) 0.25564(15) 0.38823(5) 0.0241(2) Uani 1 1 d . . . C2 C 0.86717(13) 0.19611(16) 0.43042(5) 0.0286(3) Uani 1 1 d . . . H2 H 0.8601 0.2194 0.4702 0.034 Uiso 1 1 calc R . . C3 C 0.97539(13) 0.10347(16) 0.41442(6) 0.0291(3) Uani 1 1 d . . . H3 H 1.0418 0.0618 0.4435 0.035 Uiso 1 1 calc R . . C4 C 0.98911(12) 0.06993(15) 0.35624(6) 0.0266(3) Uani 1 1 d . . . H4 H 1.0651 0.0074 0.3456 0.032 Uiso 1 1 calc R . . C5 C 0.89153(12) 0.12827(14) 0.31435(5) 0.0234(2) Uani 1 1 d . . . H5 H 0.9005 0.1049 0.2747 0.028 Uiso 1 1 calc R . . C6 C 0.77861(12) 0.22195(14) 0.32905(5) 0.0213(2) Uani 1 1 d . . . C7 C 0.66765(12) 0.27449(14) 0.28576(5) 0.0221(2) Uani 1 1 d . . . C8 C 0.66967(12) 0.23368(14) 0.22297(5) 0.0219(2) Uani 1 1 d . . . C9 C 0.55434(12) 0.16133(14) 0.19344(5) 0.0208(2) Uani 1 1 d . . . C10 C 0.54900(12) 0.13643(14) 0.13308(5) 0.0220(2) Uani 1 1 d . . . C11 C 0.65658(13) 0.19864(14) 0.10284(5) 0.0237(2) Uani 1 1 d . . . C12 C 0.77209(12) 0.27518(14) 0.13239(5) 0.0230(2) Uani 1 1 d . . . C13 C 0.77807(12) 0.28788(14) 0.19202(5) 0.0227(2) Uani 1 1 d . . . H13 H 0.8577 0.3346 0.2126 0.027 Uiso 1 1 calc R . . C14 C 0.43648(12) 0.11439(14) 0.22741(5) 0.0223(2) Uani 1 1 d . . . C15 C 0.20181(13) 0.15484(18) 0.23810(7) 0.0359(3) Uani 1 1 d . . . H15A H 0.1755 0.0424 0.2275 0.054 Uiso 1 1 calc R . . H15B H 0.1258 0.2288 0.2252 0.054 Uiso 1 1 calc R . . H15C H 0.2217 0.1628 0.2803 0.054 Uiso 1 1 calc R . . C16 C 0.43573(12) 0.04657(14) 0.09977(5) 0.0234(2) Uani 1 1 d . . . C17 C 0.24731(13) -0.13329(16) 0.10103(6) 0.0320(3) Uani 1 1 d . . . H17A H 0.1806 -0.0545 0.0829 0.048 Uiso 1 1 calc R . . H17B H 0.2022 -0.2018 0.1283 0.048 Uiso 1 1 calc R . . H17C H 0.2818 -0.2022 0.0710 0.048 Uiso 1 1 calc R . . C18 C 0.88302(13) 0.34492(15) 0.09860(5) 0.0255(2) Uani 1 1 d . . . H18A H 0.9406 0.4212 0.1238 0.031 Uiso 1 1 calc R . . H18B H 0.8392 0.4080 0.0653 0.031 Uiso 1 1 calc R . . C19 C 0.97583(13) 0.21332(16) 0.07611(6) 0.0288(3) Uani 1 1 d . . . H19A H 1.0311 0.1625 0.1095 0.035 Uiso 1 1 calc R . . H19B H 0.9170 0.1272 0.0565 0.035 Uiso 1 1 calc R . . C20 C 1.07235(14) 0.27798(17) 0.03433(6) 0.0324(3) Uani 1 1 d . . . H20A H 1.0176 0.3288 0.0008 0.039 Uiso 1 1 calc R . . H20B H 1.1253 0.1861 0.0196 0.039 Uiso 1 1 calc R . . O1 O 0.66227(10) 0.34201(12) 0.40624(4) 0.0328(2) Uani 1 1 d . . . O2 O 0.56691(9) 0.35216(11) 0.30020(4) 0.0297(2) Uani 1 1 d . . . O3 O 0.44564(9) 0.01574(11) 0.26599(4) 0.0306(2) Uani 1 1 d . . . O4 O 0.32344(8) 0.19975(10) 0.21045(4) 0.02651(19) Uani 1 1 d . . . O5 O 0.41410(10) 0.05336(12) 0.04715(4) 0.0321(2) Uani 1 1 d . . . O6 O 0.36167(9) -0.04664(11) 0.13185(4) 0.0281(2) Uani 1 1 d . . . O7 O 0.65623(10) 0.18862(12) 0.04499(4) 0.0309(2) Uani 1 1 d . . . Cl1 Cl 1.19038(4) 0.42576(5) 0.067964(19) 0.05002(12) Uani 1 1 d . . . H1 H 0.6091(19) 0.360(2) 0.3744(9) 0.052(5) Uiso 1 1 d . . . H7 H 0.580(2) 0.139(2) 0.0306(9) 0.063(6) Uiso 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 0.0252(6) 0.0247(6) 0.0230(6) -0.0019(5) 0.0051(5) -0.0025(5) C2 0.0296(6) 0.0355(7) 0.0205(6) -0.0015(5) 0.0010(5) -0.0036(5) C3 0.0251(6) 0.0341(7) 0.0271(6) 0.0041(5) -0.0019(5) -0.0027(5) C4 0.0209(6) 0.0282(6) 0.0309(6) 0.0009(5) 0.0029(5) -0.0004(5) C5 0.0243(6) 0.0238(6) 0.0227(6) -0.0022(5) 0.0045(5) -0.0026(4) C6 0.0221(6) 0.0206(5) 0.0212(6) -0.0008(4) 0.0022(4) -0.0034(4) C7 0.0223(6) 0.0219(5) 0.0225(6) -0.0012(4) 0.0043(5) -0.0026(4) C8 0.0229(6) 0.0220(6) 0.0208(6) -0.0001(4) 0.0027(5) 0.0025(4) C9 0.0209(5) 0.0204(5) 0.0213(6) 0.0012(4) 0.0023(4) 0.0021(4) C10 0.0224(6) 0.0218(5) 0.0218(6) -0.0006(4) 0.0020(4) 0.0005(4) C11 0.0273(6) 0.0248(6) 0.0192(6) -0.0011(5) 0.0033(5) 0.0013(5) C12 0.0232(6) 0.0219(5) 0.0242(6) -0.0007(5) 0.0048(5) 0.0005(4) C13 0.0204(6) 0.0241(6) 0.0235(6) -0.0021(5) 0.0022(4) 0.0000(4) C14 0.0227(6) 0.0230(6) 0.0211(6) -0.0016(5) 0.0020(5) -0.0005(4) C15 0.0215(6) 0.0405(7) 0.0469(8) -0.0038(6) 0.0098(6) -0.0015(5) C16 0.0220(5) 0.0245(6) 0.0238(6) -0.0017(5) 0.0028(5) 0.0014(4) C17 0.0262(6) 0.0311(7) 0.0377(7) -0.0039(5) -0.0016(6) -0.0062(5) C18 0.0271(6) 0.0251(6) 0.0252(6) -0.0011(5) 0.0070(5) -0.0020(5) C19 0.0288(6) 0.0277(6) 0.0314(7) 0.0002(5) 0.0101(5) -0.0019(5) C20 0.0318(7) 0.0364(7) 0.0304(7) -0.0034(6) 0.0100(5) -0.0033(6) O1 0.0349(5) 0.0414(5) 0.0225(5) -0.0042(4) 0.0056(4) 0.0104(4) O2 0.0281(5) 0.0362(5) 0.0253(4) -0.0026(4) 0.0044(4) 0.0080(4) O3 0.0285(5) 0.0346(5) 0.0290(5) 0.0099(4) 0.0044(4) -0.0004(4) O4 0.0204(4) 0.0288(4) 0.0307(5) 0.0015(4) 0.0043(3) 0.0028(3) O5 0.0334(5) 0.0407(5) 0.0214(4) -0.0013(4) -0.0017(4) -0.0070(4) O6 0.0285(4) 0.0297(5) 0.0258(4) -0.0011(4) 0.0011(4) -0.0080(4) O7 0.0330(5) 0.0416(5) 0.0184(4) -0.0029(4) 0.0042(4) -0.0086(4) Cl1 0.03372(19) 0.0600(3) 0.0583(2) -0.01400(19) 0.01490(17) -0.01998(17) _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 1.3476(15) . ? C1 C2 1.3916(17) . ? C1 C6 1.4105(16) . ? C2 C3 1.3764(19) . ? C3 C4 1.3932(18) . ? C4 C5 1.3752(17) . ? C5 C6 1.4076(17) . ? C6 C7 1.4646(16) . ? C7 O2 1.2403(14) . ? C7 C8 1.4932(16) . ? C8 C9 1.3885(16) . ? C8 C13 1.4022(17) . ? C9 C10 1.4080(16) . ? C9 C14 1.5008(16) . ? C10 C11 1.4086(17) . ? C10 C16 1.4781(16) . ? C11 O7 1.3412(14) . ? C11 C12 1.4050(17) . ? C12 C13 1.3797(17) . ? C12 C18 1.5045(17) . ? C14 O3 1.2009(14) . ? C14 O4 1.3295(14) . ? C15 O4 1.4453(15) . ? C16 O5 1.2173(15) . ? C16 O6 1.3247(15) . ? C17 O6 1.4477(15) . ? C18 C19 1.5285(17) . ? C19 C20 1.5068(18) . ? C20 Cl1 1.7931(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 117.66(11) . . ? O1 C1 C6 122.10(11) . . ? C2 C1 C6 120.22(11) . . ? C3 C2 C1 119.96(12) . . ? C2 C3 C4 121.02(12) . . ? C5 C4 C3 119.29(12) . . ? C4 C5 C6 121.34(11) . . ? C5 C6 C1 118.17(11) . . ? C5 C6 C7 122.34(11) . . ? C1 C6 C7 119.33(11) . . ? O2 C7 C6 121.00(11) . . ? O2 C7 C8 117.49(10) . . ? C6 C7 C8 121.49(10) . . ? C9 C8 C13 119.64(11) . . ? C9 C8 C7 119.27(10) . . ? C13 C8 C7 120.49(10) . . ? C8 C9 C10 120.08(11) . . ? C8 C9 C14 118.20(10) . . ? C10 C9 C14 121.71(10) . . ? C9 C10 C11 118.84(10) . . ? C9 C10 C16 122.96(10) . . ? C11 C10 C16 118.19(10) . . ? O7 C11 C12 116.00(11) . . ? O7 C11 C10 122.90(11) . . ? C12 C11 C10 121.09(11) . . ? C13 C12 C11 118.38(11) . . ? C13 C12 C18 121.88(11) . . ? C11 C12 C18 119.71(11) . . ? C12 C13 C8 121.72(11) . . ? O3 C14 O4 124.98(11) . . ? O3 C14 C9 123.78(11) . . ? O4 C14 C9 111.21(10) . . ? O5 C16 O6 122.42(11) . . ? O5 C16 C10 123.19(11) . . ? O6 C16 C10 114.35(10) . . ? C12 C18 C19 112.69(10) . . ? C20 C19 C18 113.28(11) . . ? C19 C20 Cl1 111.75(9) . . ? C14 O4 C15 115.08(10) . . ? C16 O6 C17 116.06(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.037 # Attachment 'ks1279.cif' # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF, VERSION DEC95) # This electronic data deposition form must be associated with CIF # output and can be used : # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.ac.uk # or via the WWW at http://www.iucr.ac.uk/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- #1 Data block identification for start of deposition data_ks1279 _database_code_depnum_ccdc_archive 'CCDC 832483' #TrackingRef 'ks1279.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 Br O7' _chemical_formula_weight 633.60 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0595(4) _cell_length_b 11.5721(5) _cell_length_c 15.5179(6) _cell_angle_alpha 73.732(3) _cell_angle_beta 84.917(3) _cell_angle_gamma 87.568(3) _cell_volume 1555.32(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8225 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 29.66 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5578 _exptl_absorpt_correction_T_max 0.8415 _exptl_absorpt_process_details 'X-SHAPE and X-RED32 (Stoe & Cie, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29997 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 29.22 _reflns_number_total 8406 _reflns_number_gt 6072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8406 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0633 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _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 -0.10059(2) 0.049038(18) 0.188857(15) 0.02815(6) Uani 1 1 d . . . C1 C 0.14974(18) -0.06194(15) 0.12003(12) 0.0200(3) Uani 1 1 d . . . H1B H 0.1313 -0.1258 0.1734 0.024 Uiso 1 1 calc R . . C2 C 0.06262(18) 0.04090(15) 0.10498(12) 0.0212(4) Uani 1 1 d . . . C3 C 0.08944(19) 0.13629(15) 0.02875(13) 0.0254(4) Uani 1 1 d . . . H3 H 0.0292 0.2072 0.0198 0.031 Uiso 1 1 calc R . . C4 C 0.2038(2) 0.12801(15) -0.03402(13) 0.0254(4) Uani 1 1 d . . . H4 H 0.2234 0.1939 -0.0859 0.030 Uiso 1 1 calc R . . C5 C 0.29133(18) 0.02320(15) -0.02188(12) 0.0192(3) Uani 1 1 d . . . C6 C 0.26553(17) -0.07237(14) 0.05667(11) 0.0178(3) Uani 1 1 d . . . C7 C 0.35497(17) -0.18451(14) 0.06890(12) 0.0179(3) Uani 1 1 d . . . C8 C 0.34683(17) -0.27450(14) 0.15976(11) 0.0172(3) Uani 1 1 d . . . C9 C 0.29223(17) -0.38821(14) 0.17220(11) 0.0175(3) Uani 1 1 d . . . C10 C 0.28934(17) -0.47212(14) 0.25774(12) 0.0183(3) Uani 1 1 d . . . C11 C 0.35299(17) -0.44169(14) 0.32791(11) 0.0179(3) Uani 1 1 d . . . C12 C 0.41339(17) -0.32720(15) 0.31462(12) 0.0176(3) Uani 1 1 d . . . C13 C 0.40526(17) -0.24495(14) 0.23152(11) 0.0176(3) Uani 1 1 d . . . H13 H 0.4402 -0.1659 0.2225 0.021 Uiso 1 1 calc R . . C14 C 0.24126(19) -0.41906(15) 0.09156(12) 0.0219(4) Uani 1 1 d . . . C15 C 0.2870(3) -0.54953(19) -0.00106(14) 0.0386(5) Uani 1 1 d . . . H15A H 0.1824 -0.5718 0.0102 0.058 Uiso 1 1 calc R . . H15B H 0.3484 -0.6206 -0.0033 0.058 Uiso 1 1 calc R . . H15C H 0.3015 -0.4874 -0.0586 0.058 Uiso 1 1 calc R . . C16 C 0.21754(18) -0.59055(15) 0.27928(12) 0.0209(4) Uani 1 1 d . . . C17 C 0.0684(2) -0.71651(17) 0.22846(15) 0.0324(5) Uani 1 1 d . . . H17A H 0.1477 -0.7761 0.2261 0.049 Uiso 1 1 calc R . . H17B H 0.0032 -0.7114 0.1803 0.049 Uiso 1 1 calc R . . H17C H 0.0109 -0.7409 0.2870 0.049 Uiso 1 1 calc R . . C18 C 0.48329(18) -0.30209(15) 0.39222(11) 0.0193(3) Uani 1 1 d . . . H18A H 0.5616 -0.3639 0.4117 0.023 Uiso 1 1 calc R . . H18B H 0.4068 -0.3113 0.4432 0.023 Uiso 1 1 calc R . . C19 C 0.55119(18) -0.17856(15) 0.37286(12) 0.0193(3) Uani 1 1 d . . . H19A H 0.4731 -0.1159 0.3554 0.023 Uiso 1 1 calc R . . H19B H 0.6272 -0.1678 0.3214 0.023 Uiso 1 1 calc R . . C20 C 0.62223(18) -0.16173(15) 0.45379(12) 0.0198(3) Uani 1 1 d . . . H20A H 0.5471 -0.1763 0.5058 0.024 Uiso 1 1 calc R . . H20B H 0.7028 -0.2226 0.4696 0.024 Uiso 1 1 calc R . . C21 C 0.68532(18) -0.03709(15) 0.43761(12) 0.0206(3) Uani 1 1 d . . . H21A H 0.6052 0.0237 0.4199 0.025 Uiso 1 1 calc R . . H21B H 0.7623 -0.0236 0.3866 0.025 Uiso 1 1 calc R . . C22 C 0.75286(18) -0.01727(15) 0.51855(12) 0.0211(3) Uani 1 1 d . . . H22A H 0.8331 -0.0778 0.5365 0.025 Uiso 1 1 calc R . . H22B H 0.6760 -0.0300 0.5696 0.025 Uiso 1 1 calc R . . C23 C 0.81554(18) 0.10810(15) 0.50012(12) 0.0214(4) Uani 1 1 d . . . H23A H 0.7357 0.1684 0.4804 0.026 Uiso 1 1 calc R . . H23B H 0.8938 0.1198 0.4499 0.026 Uiso 1 1 calc R . . C24 C 0.88059(19) 0.13163(15) 0.58086(12) 0.0219(4) Uani 1 1 d . . . H24A H 0.8021 0.1217 0.6309 0.026 Uiso 1 1 calc R . . H24B H 0.9597 0.0710 0.6012 0.026 Uiso 1 1 calc R . . C25 C 0.94454(19) 0.25697(16) 0.55990(12) 0.0225(4) Uani 1 1 d . . . H25A H 0.8650 0.3175 0.5399 0.027 Uiso 1 1 calc R . . H25B H 1.0222 0.2670 0.5094 0.027 Uiso 1 1 calc R . . C26 C 1.01113(19) 0.28174(15) 0.63957(12) 0.0219(4) Uani 1 1 d . . . H26A H 0.9325 0.2754 0.6891 0.026 Uiso 1 1 calc R . . H26B H 1.0876 0.2192 0.6613 0.026 Uiso 1 1 calc R . . C27 C 1.08079(19) 0.40504(16) 0.61711(12) 0.0227(4) Uani 1 1 d . . . H27A H 1.0031 0.4676 0.5983 0.027 Uiso 1 1 calc R . . H27B H 1.1558 0.4129 0.5655 0.027 Uiso 1 1 calc R . . C28 C 1.15435(19) 0.42803(15) 0.69511(12) 0.0223(4) Uani 1 1 d . . . H28A H 1.0787 0.4238 0.7459 0.027 Uiso 1 1 calc R . . H28B H 1.2294 0.3637 0.7156 0.027 Uiso 1 1 calc R . . C29 C 1.2288(2) 0.54971(16) 0.67029(12) 0.0236(4) Uani 1 1 d . . . H29A H 1.1548 0.6136 0.6466 0.028 Uiso 1 1 calc R . . H29B H 1.3080 0.5522 0.6216 0.028 Uiso 1 1 calc R . . C30 C 1.29577(19) 0.57650(15) 0.74920(12) 0.0233(4) Uani 1 1 d . . . H30A H 1.2166 0.5734 0.7980 0.028 Uiso 1 1 calc R . . H30B H 1.3701 0.5128 0.7726 0.028 Uiso 1 1 calc R . . C31 C 1.3696(2) 0.69848(16) 0.72516(12) 0.0239(4) Uani 1 1 d . . . H31A H 1.4464 0.7027 0.6749 0.029 Uiso 1 1 calc R . . H31B H 1.2945 0.7623 0.7038 0.029 Uiso 1 1 calc R . . C32 C 1.4412(2) 0.72357(15) 0.80306(12) 0.0242(4) Uani 1 1 d . . . H32A H 1.3634 0.7250 0.8518 0.029 Uiso 1 1 calc R . . H32B H 1.5116 0.6570 0.8272 0.029 Uiso 1 1 calc R . . C33 C 1.5229(2) 0.84144(17) 0.77670(14) 0.0294(4) Uani 1 1 d . . . H33A H 1.5937 0.8439 0.7247 0.044 Uiso 1 1 calc R . . H33B H 1.5762 0.8480 0.8274 0.044 Uiso 1 1 calc R . . H33C H 1.4516 0.9086 0.7610 0.044 Uiso 1 1 calc R . . O1 O 0.39874(14) 0.01868(12) -0.08662(9) 0.0244(3) Uani 1 1 d . . . O2 O 0.43585(13) -0.20459(11) 0.00700(8) 0.0254(3) Uani 1 1 d . . . O3 O 0.13985(16) -0.36996(12) 0.05042(10) 0.0373(4) Uani 1 1 d . . . O4 O 0.32906(14) -0.50354(11) 0.07060(8) 0.0259(3) Uani 1 1 d . . . O5 O 0.23177(15) -0.67011(11) 0.34818(9) 0.0323(3) Uani 1 1 d . . . O6 O 0.13256(14) -0.60011(11) 0.21671(9) 0.0270(3) Uani 1 1 d . . . O7 O 0.35869(14) -0.51873(11) 0.41048(8) 0.0248(3) Uani 1 1 d . . . H1A H 0.433(3) -0.046(2) -0.0764(16) 0.041(7) Uiso 1 1 d . . . H7 H 0.322(3) -0.584(2) 0.4104(16) 0.046(7) Uiso 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 Br1 0.02300(8) 0.02853(10) 0.03540(12) -0.01434(8) 0.00214(7) -0.00028(7) C1 0.0222(8) 0.0176(8) 0.0193(9) -0.0028(7) -0.0038(7) -0.0031(6) C2 0.0175(8) 0.0239(9) 0.0248(10) -0.0106(8) -0.0019(7) -0.0022(7) C3 0.0257(8) 0.0188(8) 0.0322(11) -0.0061(8) -0.0097(8) 0.0030(7) C4 0.0299(9) 0.0180(8) 0.0245(10) 0.0019(7) -0.0072(8) -0.0012(7) C5 0.0200(7) 0.0202(8) 0.0173(9) -0.0033(7) -0.0051(7) -0.0045(6) C6 0.0200(7) 0.0154(8) 0.0180(9) -0.0032(7) -0.0053(7) -0.0029(6) C7 0.0196(7) 0.0166(8) 0.0181(9) -0.0045(7) -0.0048(7) -0.0034(6) C8 0.0194(7) 0.0158(8) 0.0162(9) -0.0040(7) -0.0029(6) 0.0020(6) C9 0.0179(7) 0.0165(8) 0.0191(9) -0.0058(7) -0.0042(6) 0.0015(6) C10 0.0190(7) 0.0159(8) 0.0203(9) -0.0054(7) -0.0010(7) -0.0015(6) C11 0.0199(7) 0.0164(8) 0.0162(9) -0.0028(7) -0.0010(6) 0.0005(6) C12 0.0169(7) 0.0189(8) 0.0181(9) -0.0068(7) -0.0023(6) 0.0002(6) C13 0.0189(7) 0.0142(7) 0.0199(9) -0.0046(7) -0.0016(7) -0.0018(6) C14 0.0282(9) 0.0154(8) 0.0214(9) -0.0021(7) -0.0071(7) -0.0040(7) C15 0.0609(14) 0.0338(11) 0.0262(11) -0.0149(9) -0.0063(10) -0.0057(10) C16 0.0233(8) 0.0167(8) 0.0236(10) -0.0070(7) -0.0006(7) -0.0019(7) C17 0.0325(10) 0.0256(10) 0.0437(13) -0.0156(9) -0.0018(9) -0.0118(8) C18 0.0229(8) 0.0190(8) 0.0163(9) -0.0048(7) -0.0032(7) -0.0022(7) C19 0.0215(8) 0.0194(8) 0.0180(9) -0.0060(7) -0.0031(7) -0.0021(6) C20 0.0219(8) 0.0207(8) 0.0181(9) -0.0067(7) -0.0030(7) -0.0032(7) C21 0.0212(8) 0.0212(8) 0.0204(9) -0.0070(7) -0.0028(7) -0.0029(7) C22 0.0221(8) 0.0219(8) 0.0203(9) -0.0064(7) -0.0022(7) -0.0045(7) C23 0.0210(8) 0.0236(9) 0.0207(9) -0.0067(7) -0.0040(7) -0.0032(7) C24 0.0226(8) 0.0222(8) 0.0224(10) -0.0076(7) -0.0037(7) -0.0043(7) C25 0.0224(8) 0.0244(9) 0.0227(10) -0.0085(8) -0.0032(7) -0.0042(7) C26 0.0237(8) 0.0228(8) 0.0205(9) -0.0076(7) -0.0022(7) -0.0038(7) C27 0.0244(8) 0.0243(9) 0.0210(9) -0.0084(8) -0.0019(7) -0.0048(7) C28 0.0256(8) 0.0213(8) 0.0216(10) -0.0080(7) -0.0025(7) -0.0037(7) C29 0.0284(9) 0.0231(9) 0.0207(10) -0.0075(8) -0.0028(7) -0.0041(7) C30 0.0272(9) 0.0220(9) 0.0216(10) -0.0066(8) -0.0052(7) -0.0017(7) C31 0.0291(9) 0.0236(9) 0.0198(10) -0.0060(7) -0.0055(7) -0.0032(7) C32 0.0299(9) 0.0226(9) 0.0214(10) -0.0070(8) -0.0059(7) -0.0008(7) C33 0.0310(9) 0.0305(10) 0.0293(11) -0.0116(9) -0.0034(8) -0.0054(8) O1 0.0271(6) 0.0222(7) 0.0204(7) -0.0005(5) -0.0003(5) -0.0012(5) O2 0.0336(7) 0.0218(6) 0.0202(7) -0.0062(5) 0.0007(5) 0.0017(5) O3 0.0462(8) 0.0265(7) 0.0434(9) -0.0104(7) -0.0286(7) 0.0075(6) O4 0.0365(7) 0.0231(6) 0.0212(7) -0.0103(5) -0.0066(6) 0.0021(5) O5 0.0456(8) 0.0194(6) 0.0291(8) 0.0005(6) -0.0084(6) -0.0085(6) O6 0.0322(7) 0.0214(6) 0.0293(8) -0.0076(6) -0.0066(6) -0.0094(5) O7 0.0364(7) 0.0186(6) 0.0175(7) -0.0003(5) -0.0053(5) -0.0070(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.8988(17) . ? C1 C2 1.375(2) . ? C1 C6 1.398(2) . ? C2 C3 1.385(3) . ? C3 C4 1.377(3) . ? C4 C5 1.397(2) . ? C5 O1 1.346(2) . ? C5 C6 1.407(2) . ? C6 C7 1.475(2) . ? C7 O2 1.2245(19) . ? C7 C8 1.498(2) . ? C8 C9 1.382(2) . ? C8 C13 1.404(2) . ? C9 C10 1.407(2) . ? C9 C14 1.508(2) . ? C10 C11 1.409(2) . ? C10 C16 1.481(2) . ? C11 O7 1.344(2) . ? C11 C12 1.409(2) . ? C12 C13 1.377(2) . ? C12 C18 1.511(2) . ? C14 O3 1.196(2) . ? C14 O4 1.327(2) . ? C15 O4 1.445(2) . ? C16 O5 1.213(2) . ? C16 O6 1.322(2) . ? C17 O6 1.448(2) . ? C18 C19 1.521(2) . ? C19 C20 1.523(2) . ? C20 C21 1.520(2) . ? C21 C22 1.521(2) . ? C22 C23 1.522(2) . ? C23 C24 1.525(2) . ? C24 C25 1.523(2) . ? C25 C26 1.523(2) . ? C26 C27 1.521(2) . ? C27 C28 1.523(2) . ? C28 C29 1.522(2) . ? C29 C30 1.524(2) . ? C30 C31 1.523(2) . ? C31 C32 1.522(2) . ? C32 C33 1.515(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 C2 C1 C6 119.87(16) . . ? C1 C2 C3 121.14(16) . . ? C1 C2 Br1 118.97(14) . . ? C3 C2 Br1 119.86(12) . . ? C4 C3 C2 119.77(15) . . ? C3 C4 C5 120.35(17) . . ? O1 C5 C4 117.84(16) . . ? O1 C5 C6 122.60(14) . . ? C4 C5 C6 119.56(16) . . ? C1 C6 C5 119.25(14) . . ? C1 C6 C7 120.80(15) . . ? C5 C6 C7 119.86(15) . . ? O2 C7 C6 121.53(16) . . ? O2 C7 C8 119.81(14) . . ? C6 C7 C8 118.65(14) . . ? C9 C8 C13 119.85(15) . . ? C9 C8 C7 120.99(14) . . ? C13 C8 C7 119.01(14) . . ? C8 C9 C10 119.87(14) . . ? C8 C9 C14 118.03(15) . . ? C10 C9 C14 122.08(14) . . ? C9 C10 C11 119.10(15) . . ? C9 C10 C16 123.23(15) . . ? C11 C10 C16 117.63(16) . . ? O7 C11 C10 122.39(15) . . ? O7 C11 C12 116.55(14) . . ? C10 C11 C12 121.05(15) . . ? C13 C12 C11 117.95(14) . . ? C13 C12 C18 123.96(15) . . ? C11 C12 C18 118.09(15) . . ? C12 C13 C8 121.96(15) . . ? O3 C14 O4 125.28(16) . . ? O3 C14 C9 124.28(15) . . ? O4 C14 C9 110.37(13) . . ? O5 C16 O6 122.99(16) . . ? O5 C16 C10 123.79(16) . . ? O6 C16 C10 113.20(15) . . ? C12 C18 C19 115.68(14) . . ? C18 C19 C20 112.30(14) . . ? C21 C20 C19 113.42(14) . . ? C20 C21 C22 114.24(15) . . ? C21 C22 C23 112.97(15) . . ? C22 C23 C24 114.13(15) . . ? C25 C24 C23 112.89(15) . . ? C24 C25 C26 113.63(15) . . ? C27 C26 C25 113.38(15) . . ? C26 C27 C28 113.69(15) . . ? C29 C28 C27 112.95(15) . . ? C28 C29 C30 113.39(15) . . ? C31 C30 C29 113.78(15) . . ? C32 C31 C30 113.86(15) . . ? C33 C32 C31 113.30(16) . . ? C14 O4 C15 116.72(14) . . ? C16 O6 C17 116.85(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.22 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.568 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.056