# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_fr93 _database_code_depnum_ccdc_archive 'CCDC 906866' #TrackingRef '14798_web_deposit_cif_file_0_Commeiras_1350654207.fr93.cif' _audit_update_record ; 2012-10-19 # Formatted by publCIF ; _audit_creation_date 2010-03-02T16:27:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C13 H14 O5' _chemical_formula_sum 'C13 H14 O5' _chemical_formula_weight 250.24 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.6438(3) _cell_length_b 7.4285(2) _cell_length_c 8.7806(4) _cell_angle_alpha 90 _cell_angle_beta 94.451(1) _cell_angle_gamma 90 _cell_volume 562.11(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5158 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_number 5158 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.7 _diffrn_reflns_theta_full 28.7 _diffrn_measured_fraction_theta_full 0.957 _diffrn_measured_fraction_theta_max 0.957 _reflns_number_total 1493 _reflns_number_gt 1293 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 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^ > 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^)+(0.0975P)^2^+0.0402P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1493 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1548 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(18) _refine_diff_density_max 0.243 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.076 #----------------------------------------------------------------------------# # 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 C1 C 0.7731(3) 0.5894(4) 0.8241(3) 0.0289(6) Uani 1 1 d . . . C2 C 0.9432(3) 0.6321(4) 0.8003(3) 0.0317(6) Uani 1 1 d . . . H2 H 0.9555 0.7532 0.7587 0.038 Uiso 1 1 calc R . . C3 C 1.0615(4) 0.5939(7) 0.9365(4) 0.0540(10) Uani 1 1 d . . . H3A H 1.0948 0.7059 0.9856 0.065 Uiso 1 1 calc R . . H3B H 1.0149 0.5191 1.011 0.065 Uiso 1 1 calc R . . C4 C 1.1592(4) 0.4555(6) 0.7273(4) 0.0463(9) Uani 1 1 d . . . H4A H 1.1863 0.3301 0.7135 0.056 Uiso 1 1 calc R . . H4B H 1.2198 0.5289 0.6627 0.056 Uiso 1 1 calc R . . C5 C 0.9868(3) 0.4846(4) 0.6875(3) 0.0328(6) Uani 1 1 d . . . C6 C 0.9316(4) 0.5226(5) 0.5236(3) 0.0408(7) Uani 1 1 d . . . H6 H 1.0007 0.561 0.4543 0.049 Uiso 1 1 calc R . . C7 C 0.7823(4) 0.5003(5) 0.4803(3) 0.0424(7) Uani 1 1 d . . . H7 H 0.7478 0.5174 0.3784 0.051 Uiso 1 1 calc R . . C8 C 0.6679(4) 0.4479(4) 0.5933(4) 0.0389(7) Uani 1 1 d . . . H8 H 0.6055 0.3452 0.5544 0.047 Uiso 1 1 calc R . . C9 C 0.7502(3) 0.4021(4) 0.7501(3) 0.0327(6) Uani 1 1 d . . . H9 H 0.687 0.3232 0.8097 0.039 Uiso 1 1 calc R . . C10 C 0.6418(3) 0.7067(4) 0.7450(4) 0.0352(6) Uani 1 1 d . . . C11 C 0.5304(4) 0.7317(6) 0.8691(4) 0.0489(9) Uani 1 1 d . . . H11A H 0.5018 0.8575 0.8771 0.059 Uiso 1 1 calc R . . H11B H 0.4368 0.6616 0.846 0.059 Uiso 1 1 calc R . . C12 C 0.6134(4) 0.6688(5) 1.0145(4) 0.0389(7) Uani 1 1 d . . . C13 C 0.6909(4) 0.8853(5) 0.6807(5) 0.0480(8) Uani 1 1 d . . . H13A H 0.7596 0.8642 0.6017 0.072 Uiso 1 1 calc R . . H13B H 0.7434 0.9554 0.7607 0.072 Uiso 1 1 calc R . . H13C H 0.6009 0.9493 0.639 0.072 Uiso 1 1 calc R . . O1 O 1.1880(3) 0.5058(5) 0.8813(3) 0.0583(8) Uani 1 1 d . . . O2 O 0.9011(3) 0.3306(3) 0.7371(2) 0.0349(5) Uani 1 1 d . . . O3 O 0.5686(2) 0.5968(4) 0.6240(3) 0.0449(6) Uani 1 1 d . . . O4 O 0.7481(2) 0.5870(3) 0.9853(2) 0.0375(5) Uani 1 1 d . . . O5 O 0.5732(3) 0.6765(4) 1.1417(3) 0.0518(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0271(12) 0.0313(13) 0.0280(12) 0.0006(11) 0.0004(10) -0.0009(11) C2 0.0278(12) 0.0311(15) 0.0359(14) -0.0046(10) 0.0004(10) -0.0011(10) C3 0.0386(16) 0.076(3) 0.0454(18) -0.0226(19) -0.0134(14) 0.0177(18) C4 0.0311(15) 0.061(2) 0.0461(18) -0.0146(16) -0.0019(13) 0.0085(14) C5 0.0316(14) 0.0336(15) 0.0329(14) -0.0028(11) 0.0003(11) 0.0020(11) C6 0.0491(17) 0.0453(18) 0.0281(14) 0.0019(13) 0.0037(13) 0.0025(14) C7 0.0528(19) 0.0425(17) 0.0302(14) 0.0019(13) -0.0088(13) 0.0001(15) C8 0.0384(15) 0.0361(17) 0.0402(16) -0.0039(12) -0.0101(12) -0.0023(12) C9 0.0327(14) 0.0284(14) 0.0363(15) 0.0007(11) -0.0011(11) -0.0017(11) C10 0.0305(14) 0.0321(15) 0.0421(15) 0.0004(12) -0.0038(12) 0.0030(11) C11 0.0342(16) 0.058(2) 0.055(2) 0.0015(17) 0.0053(14) 0.0110(15) C12 0.0340(14) 0.0363(16) 0.0473(17) -0.0018(14) 0.0086(13) -0.0047(12) C13 0.0492(19) 0.0363(18) 0.056(2) 0.0109(14) -0.0096(16) 0.0008(14) O1 0.0402(12) 0.087(2) 0.0455(13) -0.0228(14) -0.0128(10) 0.0220(14) O2 0.0403(11) 0.0272(10) 0.0363(11) 0.0008(8) -0.0026(9) 0.0037(8) O3 0.0357(11) 0.0453(13) 0.0503(13) -0.0049(11) -0.0177(10) 0.0038(10) O4 0.0401(11) 0.0424(11) 0.0302(10) 0.0016(9) 0.0040(8) 0.0049(10) O5 0.0517(14) 0.0586(17) 0.0476(14) -0.0062(12) 0.0188(12) -0.0052(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 1.448(3) . ? C1 C2 1.534(4) . ? C1 C9 1.542(4) . ? C1 C10 1.552(4) . ? C2 C3 1.539(4) . ? C2 C5 1.543(4) . ? C2 H2 0.98 . ? C3 O1 1.393(4) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 O1 1.406(4) . ? C4 C5 1.520(4) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 O2 1.448(4) . ? C5 C6 1.507(4) . ? C6 C7 1.327(5) . ? C6 H6 0.93 . ? C7 C8 1.506(5) . ? C7 H7 0.93 . ? C8 O3 1.439(4) . ? C8 C9 1.537(4) . ? C8 H8 0.98 . ? C9 O2 1.421(4) . ? C9 H9 0.98 . ? C10 O3 1.446(4) . ? C10 C13 1.515(5) . ? C10 C11 1.521(5) . ? C11 C12 1.491(5) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 O5 1.197(4) . ? C12 O4 1.355(4) . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? 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 O4 C1 C2 110.7(2) . . ? O4 C1 C9 112.1(2) . . ? C2 C1 C9 102.8(2) . . ? O4 C1 C10 106.6(2) . . ? C2 C1 C10 119.9(3) . . ? C9 C1 C10 104.6(2) . . ? C1 C2 C3 116.2(3) . . ? C1 C2 C5 103.0(2) . . ? C3 C2 C5 100.8(2) . . ? C1 C2 H2 111.9 . . ? C3 C2 H2 111.9 . . ? C5 C2 H2 111.9 . . ? O1 C3 C2 108.0(3) . . ? O1 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O1 C4 C5 106.3(3) . . ? O1 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? O1 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? O2 C5 C6 107.7(2) . . ? O2 C5 C4 109.5(3) . . ? C6 C5 C4 118.6(3) . . ? O2 C5 C2 102.2(2) . . ? C6 C5 C2 113.9(3) . . ? C4 C5 C2 103.7(2) . . ? C7 C6 C5 118.6(3) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C8 121.1(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? O3 C8 C7 110.9(3) . . ? O3 C8 C9 104.1(2) . . ? C7 C8 C9 111.4(3) . . ? O3 C8 H8 110.1 . . ? C7 C8 H8 110.1 . . ? C9 C8 H8 110.1 . . ? O2 C9 C8 112.0(2) . . ? O2 C9 C1 106.4(2) . . ? C8 C9 C1 102.3(2) . . ? O2 C9 H9 111.9 . . ? C8 C9 H9 111.9 . . ? C1 C9 H9 111.9 . . ? O3 C10 C13 109.9(3) . . ? O3 C10 C11 109.3(3) . . ? C13 C10 C11 111.8(3) . . ? O3 C10 C1 106.0(2) . . ? C13 C10 C1 116.2(3) . . ? C11 C10 C1 103.3(3) . . ? C12 C11 C10 106.6(3) . . ? C12 C11 H11A 110.4 . . ? C10 C11 H11A 110.4 . . ? C12 C11 H11B 110.4 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? O5 C12 O4 120.9(3) . . ? O5 C12 C11 129.0(3) . . ? O4 C12 C11 110.0(3) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 O1 C4 112.0(2) . . ? C9 O2 C5 102.9(2) . . ? C8 O3 C10 109.8(2) . . ? C12 O4 C1 112.0(2) . . ? # END of CIF data_fr909c _database_code_depnum_ccdc_archive 'CCDC 907998' #TrackingRef '14981_web_deposit_cif_file_0_COMMEIRAS_1351260021.fr909c.cif' _audit_creation_date 2012-10-25T11:12:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H22 O7' _chemical_formula_sum 'C18 H22 O7' _chemical_formula_weight 350.36 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 13.6639(4) _cell_length_b 11.0259(2) _cell_length_c 11.8705(2) _cell_angle_alpha 90 _cell_angle_beta 106.134(1) _cell_angle_gamma 90 _cell_volume 1717.94(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16806 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 29.02 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.083 _diffrn_reflns_av_unetI/netI 0.0488 _diffrn_reflns_number 16806 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 29.02 _diffrn_reflns_theta_full 29.02 _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.965 _reflns_number_total 4402 _reflns_number_gt 2713 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 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^)+(0.1214P)^2^+0.2069P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4402 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1234 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.2227 _refine_ls_wR_factor_gt 0.17 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.652 _refine_diff_density_min -0.926 _refine_diff_density_rms 0.273 #----------------------------------------------------------------------------# # 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 C1 C 0.71444(16) 0.1568(2) 0.78683(17) 0.0338(5) Uani 1 1 d . . . C2 C 0.82283(15) 0.09889(19) 0.81815(17) 0.0311(4) Uani 1 1 d . . . C3 C 0.86386(17) 0.0508(2) 0.94560(19) 0.0420(5) Uani 1 1 d . . . C4 C 0.8931(2) 0.1442(3) 1.0420(2) 0.0543(7) Uani 1 1 d . . . H4A H 0.9527 0.1152 1.1011 0.065 Uiso 1 1 calc R . . H4B H 0.8381 0.1507 1.0786 0.065 Uiso 1 1 calc R . . C5 C 0.9162(2) 0.2709(3) 1.0037(2) 0.0545(7) Uani 1 1 d . . . H5A H 0.8999 0.3312 1.0551 0.065 Uiso 1 1 calc R . . H5B H 0.9882 0.2774 1.0091 0.065 Uiso 1 1 calc R . . C6 C 0.85390(17) 0.2940(2) 0.87877(19) 0.0405(5) Uani 1 1 d . . . C7 C 0.73679(17) 0.2778(2) 0.8545(2) 0.0393(5) Uani 1 1 d . . . H7 H 0.7177 0.2732 0.9281 0.047 Uiso 1 1 calc R . . C8 C 0.6156(2) 0.0427(3) 0.9176(2) 0.0634(8) Uani 1 1 d . . . H8A H 0.5503 0.0052 0.9072 0.095 Uiso 1 1 calc R . . H8B H 0.6225 0.1097 0.9708 0.095 Uiso 1 1 calc R . . H8C H 0.6683 -0.0156 0.9491 0.095 Uiso 1 1 calc R . . C9 C 0.62452(17) 0.0871(2) 0.8021(2) 0.0422(5) Uani 1 1 d . . . C10 C 0.55668(19) 0.0767(3) 0.6978(2) 0.0540(7) Uani 1 1 d . . . H10 H 0.4931 0.0401 0.6844 0.065 Uiso 1 1 calc R . . C11 C 0.59628(17) 0.1306(3) 0.6078(2) 0.0485(6) Uani 1 1 d . . . C12 C 0.83461(17) -0.00085(19) 0.73381(18) 0.0346(5) Uani 1 1 d . . . C13 C 0.7593(2) -0.1977(2) 0.6590(2) 0.0444(6) Uani 1 1 d . . . C14 C 0.7449(3) -0.1722(3) 0.5306(2) 0.0762(10) Uani 1 1 d . . . H14A H 0.6863 -0.1214 0.5015 0.114 Uiso 1 1 calc R . . H14B H 0.7351 -0.2472 0.4878 0.114 Uiso 1 1 calc R . . H14C H 0.8042 -0.1318 0.5206 0.114 Uiso 1 1 calc R . . C15 C 0.6677(2) -0.2612(3) 0.6798(3) 0.0618(7) Uani 1 1 d . . . H15A H 0.6776 -0.2713 0.7626 0.093 Uiso 1 1 calc R . . H15B H 0.6596 -0.3392 0.6425 0.093 Uiso 1 1 calc R . . H15C H 0.6078 -0.2133 0.6477 0.093 Uiso 1 1 calc R . . C16 C 0.8561(2) -0.2675(2) 0.7151(2) 0.0566(7) Uani 1 1 d . . . H16A H 0.913 -0.2272 0.6991 0.085 Uiso 1 1 calc R . . H16B H 0.8504 -0.3482 0.6835 0.085 Uiso 1 1 calc R . . H16C H 0.8661 -0.2715 0.7984 0.085 Uiso 1 1 calc R . . C17 C 0.8640(2) 0.4175(2) 0.8279(2) 0.0507(6) Uani 1 1 d . . . H17A H 0.8732 0.4797 0.8877 0.061 Uiso 1 1 calc R . . H17B H 0.9218 0.4193 0.7954 0.061 Uiso 1 1 calc R . . C18 C 0.6937(2) 0.3916(2) 0.7865(3) 0.0528(6) Uani 1 1 d . . . H18A H 0.6325 0.3727 0.7246 0.063 Uiso 1 1 calc R . . H18B H 0.6771 0.4515 0.8381 0.063 Uiso 1 1 calc R . . O1 O 0.88322(10) 0.20063(13) 0.80738(12) 0.0337(4) Uani 1 1 d . . . O2 O 0.87461(16) -0.05575(19) 0.96490(16) 0.0656(6) Uani 1 1 d . . . O3 O 0.68976(11) 0.17902(14) 0.66206(12) 0.0371(4) Uani 1 1 d . . . O4 O 0.56194(15) 0.1384(2) 0.50343(16) 0.0733(6) Uani 1 1 d . . . O5 O 0.90290(14) -0.00349(15) 0.68874(16) 0.0507(5) Uani 1 1 d . . . O6 O 0.76033(12) -0.08060(14) 0.72227(13) 0.0400(4) Uani 1 1 d . . . O7 O 0.77136(14) 0.43616(16) 0.73817(16) 0.0549(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0355(11) 0.0339(12) 0.0339(10) 0.0005(8) 0.0128(8) -0.0004(9) C2 0.0331(10) 0.0300(11) 0.0313(10) -0.0011(8) 0.0108(8) -0.0014(8) C3 0.0393(12) 0.0512(15) 0.0363(12) 0.0053(10) 0.0117(9) 0.0030(11) C4 0.0554(15) 0.074(2) 0.0305(11) -0.0024(11) 0.0078(10) 0.0083(14) C5 0.0555(15) 0.0643(18) 0.0420(13) -0.0184(12) 0.0106(11) -0.0050(13) C6 0.0432(13) 0.0391(13) 0.0415(12) -0.0150(9) 0.0157(9) -0.0020(10) C7 0.0394(12) 0.0384(12) 0.0450(12) -0.0060(9) 0.0202(9) 0.0021(10) C8 0.0615(17) 0.077(2) 0.0605(17) 0.0106(14) 0.0324(13) -0.0109(16) C9 0.0383(12) 0.0428(14) 0.0502(13) 0.0018(10) 0.0201(10) -0.0027(10) C10 0.0334(12) 0.0666(18) 0.0613(16) 0.0026(12) 0.0122(11) -0.0108(12) C11 0.0378(12) 0.0562(16) 0.0471(14) 0.0009(11) 0.0046(10) -0.0032(11) C12 0.0417(12) 0.0278(11) 0.0355(11) 0.0027(8) 0.0129(9) 0.0037(9) C13 0.0645(15) 0.0268(12) 0.0387(12) -0.0029(8) 0.0092(10) -0.0009(11) C14 0.132(3) 0.0545(19) 0.0376(14) -0.0015(12) 0.0164(16) -0.0018(19) C15 0.0638(17) 0.0449(16) 0.0695(18) -0.0052(13) 0.0065(13) -0.0122(14) C16 0.0652(17) 0.0348(14) 0.0666(17) -0.0026(11) 0.0133(13) 0.0042(12) C17 0.0562(15) 0.0365(14) 0.0638(16) -0.0141(11) 0.0238(12) -0.0082(12) C18 0.0505(15) 0.0368(14) 0.0752(17) -0.0042(12) 0.0243(12) 0.0078(11) O1 0.0343(8) 0.0325(8) 0.0367(8) -0.0065(6) 0.0135(6) -0.0026(6) O2 0.0859(15) 0.0529(12) 0.0520(11) 0.0174(9) 0.0092(9) 0.0044(11) O3 0.0346(8) 0.0411(9) 0.0339(8) 0.0041(6) 0.0068(6) -0.0014(6) O4 0.0566(12) 0.1056(18) 0.0460(11) 0.0083(10) -0.0049(8) -0.0168(12) O5 0.0599(11) 0.0400(10) 0.0647(11) -0.0047(8) 0.0379(9) 0.0006(8) O6 0.0455(9) 0.0303(8) 0.0458(9) -0.0058(6) 0.0151(7) -0.0023(7) O7 0.0563(11) 0.0359(10) 0.0759(13) 0.0051(8) 0.0241(9) 0.0026(8) #----------------------------------------------------------------------------# # 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 C1 O3 1.446(2) . ? C1 C9 1.502(3) . ? C1 C7 1.544(3) . ? C1 C2 1.560(3) . ? C2 O1 1.419(2) . ? C2 C12 1.525(3) . ? C2 C3 1.553(3) . ? C3 O2 1.198(3) . ? C3 C4 1.508(4) . ? C4 C5 1.529(4) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.512(3) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 O1 1.458(2) . ? C6 C17 1.512(4) . ? C6 C7 1.555(3) . ? C7 C18 1.520(3) . ? C7 H7 0.98 . ? C8 C9 1.492(3) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 C10 1.329(3) . ? C10 C11 1.453(4) . ? C10 H10 0.93 . ? C11 O4 1.199(3) . ? C11 O3 1.369(3) . ? C12 O5 1.198(3) . ? C12 O6 1.321(3) . ? C13 O6 1.492(3) . ? C13 C14 1.509(3) . ? C13 C15 1.513(4) . ? C13 C16 1.515(4) . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 O7 1.425(3) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 O7 1.426(3) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 C1 C9 104.16(16) . . ? O3 C1 C7 110.05(17) . . ? C9 C1 C7 115.43(17) . . ? O3 C1 C2 104.43(15) . . ? C9 C1 C2 121.07(18) . . ? C7 C1 C2 101.09(16) . . ? O1 C2 C12 109.92(16) . . ? O1 C2 C3 107.22(16) . . ? C12 C2 C3 108.52(17) . . ? O1 C2 C1 101.09(15) . . ? C12 C2 C1 113.89(17) . . ? C3 C2 C1 115.70(16) . . ? O2 C3 C4 122.1(2) . . ? O2 C3 C2 120.9(2) . . ? C4 C3 C2 117.0(2) . . ? C3 C4 C5 115.6(2) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? C6 C5 C4 109.8(2) . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? O1 C6 C17 109.46(18) . . ? O1 C6 C5 106.27(19) . . ? C17 C6 C5 117.0(2) . . ? O1 C6 C7 104.24(16) . . ? C17 C6 C7 103.5(2) . . ? C5 C6 C7 115.6(2) . . ? C18 C7 C1 116.47(19) . . ? C18 C7 C6 103.3(2) . . ? C1 C7 C6 103.90(16) . . ? C18 C7 H7 110.9 . . ? C1 C7 H7 110.9 . . ? C6 C7 H7 110.9 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C8 127.8(2) . . ? C10 C9 C1 108.3(2) . . ? C8 C9 C1 123.9(2) . . ? C9 C10 C11 110.1(2) . . ? C9 C10 H10 124.9 . . ? C11 C10 H10 124.9 . . ? O4 C11 O3 120.3(2) . . ? O4 C11 C10 132.1(2) . . ? O3 C11 C10 107.6(2) . . ? O5 C12 O6 127.5(2) . . ? O5 C12 C2 123.2(2) . . ? O6 C12 C2 109.26(17) . . ? O6 C13 C14 109.2(2) . . ? O6 C13 C15 102.1(2) . . ? C14 C13 C15 111.7(2) . . ? O6 C13 C16 109.51(19) . . ? C14 C13 C16 113.1(2) . . ? C15 C13 C16 110.7(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O7 C17 C6 105.53(19) . . ? O7 C17 H17A 110.6 . . ? C6 C17 H17A 110.6 . . ? O7 C17 H17B 110.6 . . ? C6 C17 H17B 110.6 . . ? H17A C17 H17B 108.8 . . ? O7 C18 C7 106.08(19) . . ? O7 C18 H18A 110.5 . . ? C7 C18 H18A 110.5 . . ? O7 C18 H18B 110.5 . . ? C7 C18 H18B 110.5 . . ? H18A C18 H18B 108.7 . . ? C2 O1 C6 104.19(15) . . ? C11 O3 C1 109.73(16) . . ? C12 O6 C13 121.83(17) . . ? C17 O7 C18 104.8(2) . . ? # END of CIF