# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Hursthouse, Mike' 'Montis, Riccardo' 'Tizzard, Graham' _publ_contact_author_name 'Hursthouse, Mike' _publ_contact_author_email mbh@soton.ac.uk _publ_section_title ; Further crystal structures for the substituted aspirin family of molecules: the first aspirin carboxylate catemer and a detailed assessment of the subtle influences of weak intermolecular interactions ; # Attachment '- Aspirin derivatives paper 2.cif' data_3-methoxyaspirin _database_code_depnum_ccdc_archive 'CCDC 800301' #TrackingRef '- Aspirin derivatives paper 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-3-methoxybenzoic acid' ; _chemical_name_common 3-methoxyaspirin _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O5' _chemical_formula_sum 'C10 H10 O5' _chemical_formula_weight 210.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5451(3) _cell_length_b 14.2427(5) _cell_length_c 7.3811(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.716(2) _cell_angle_gamma 90.00 _cell_volume 978.83(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12090 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9497 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15755 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2245 _reflns_number_gt 1902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0465P)^2^+0.4145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2245 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.80638(13) 0.05894(9) 0.32233(17) 0.0176(3) Uani 1 1 d . . . C2 C 0.78562(13) -0.00093(9) 0.46283(17) 0.0174(3) Uani 1 1 d . . . C3 C 0.70148(13) 0.02571(9) 0.58770(17) 0.0184(3) Uani 1 1 d . . . C4 C 0.63442(15) 0.11277(10) 0.56801(18) 0.0220(3) Uani 1 1 d . . . H4 H 0.5754 0.1311 0.6500 0.026 Uiso 1 1 calc R . . C5 C 0.65432(16) 0.17314(10) 0.42694(19) 0.0245(3) Uani 1 1 d . . . H5 H 0.6080 0.2326 0.4131 0.029 Uiso 1 1 calc R . . C6 C 0.74059(15) 0.14759(9) 0.30694(18) 0.0218(3) Uani 1 1 d . . . H6 H 0.7553 0.1902 0.2139 0.026 Uiso 1 1 calc R . . C7 C 0.89288(13) 0.03098(9) 0.18497(17) 0.0176(3) Uani 1 1 d . . . C8 C 0.78314(16) -0.16056(10) 0.38248(19) 0.0236(3) Uani 1 1 d . . . C9 C 0.8678(2) -0.24912(12) 0.4224(2) 0.0426(5) Uani 1 1 d . . . H9A H 0.8723 -0.2683 0.5511 0.064 Uiso 1 1 calc R . . H9B H 0.9653 -0.2386 0.4045 0.064 Uiso 1 1 calc R . . H9C H 0.8215 -0.2986 0.3379 0.064 Uiso 1 1 calc R . . C10 C 0.60115(15) -0.01668(11) 0.84497(18) 0.0243(3) Uani 1 1 d . . . H10A H 0.6344 0.0415 0.9115 0.037 Uiso 1 1 calc R . . H10B H 0.6042 -0.0679 0.9344 0.037 Uiso 1 1 calc R . . H10C H 0.5024 -0.0084 0.7739 0.037 Uiso 1 1 calc R . . O1 O 0.90230(11) 0.09669(7) 0.06392(13) 0.0250(2) Uani 1 1 d . . . H1 H 0.9511 0.0769 -0.0099 0.037 Uiso 1 1 calc R . . O2 O 0.94803(10) -0.04751(7) 0.18329(13) 0.0237(2) Uani 1 1 d . . . O3 O 0.85095(10) -0.08895(7) 0.49149(12) 0.0208(2) Uani 1 1 d . . . O4 O 0.67146(11) -0.15000(7) 0.27181(15) 0.0291(3) Uani 1 1 d . . . O5 O 0.69259(11) -0.03907(7) 0.72059(13) 0.0234(2) 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 0.0150(6) 0.0211(6) 0.0156(6) -0.0009(5) 0.0013(5) -0.0016(5) C2 0.0143(6) 0.0204(6) 0.0163(6) -0.0012(5) 0.0007(5) 0.0012(5) C3 0.0173(6) 0.0233(7) 0.0142(6) -0.0002(5) 0.0023(5) -0.0009(5) C4 0.0221(7) 0.0246(7) 0.0196(6) -0.0050(5) 0.0053(5) 0.0015(5) C5 0.0293(7) 0.0194(6) 0.0244(7) -0.0026(5) 0.0054(6) 0.0016(6) C6 0.0267(7) 0.0189(6) 0.0196(6) 0.0003(5) 0.0047(5) -0.0029(5) C7 0.0145(6) 0.0220(7) 0.0152(6) 0.0000(5) 0.0009(5) -0.0046(5) C8 0.0328(8) 0.0226(7) 0.0191(6) 0.0027(5) 0.0136(6) 0.0050(6) C9 0.0715(13) 0.0297(8) 0.0273(8) 0.0047(6) 0.0123(8) 0.0236(8) C10 0.0203(7) 0.0378(8) 0.0164(6) 0.0004(6) 0.0073(5) 0.0011(6) O1 0.0282(5) 0.0265(5) 0.0239(5) 0.0035(4) 0.0135(4) -0.0015(4) O2 0.0249(5) 0.0242(5) 0.0246(5) 0.0005(4) 0.0108(4) 0.0012(4) O3 0.0220(5) 0.0233(5) 0.0178(4) 0.0042(4) 0.0060(4) 0.0071(4) O4 0.0298(6) 0.0252(5) 0.0327(6) -0.0036(4) 0.0076(5) -0.0006(4) O5 0.0254(5) 0.0292(5) 0.0184(5) 0.0050(4) 0.0108(4) 0.0051(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 1.3900(18) . ? C1 C6 1.4037(18) . ? C1 C7 1.4955(17) . ? C2 O3 1.3954(15) . ? C2 C3 1.4016(18) . ? C3 O5 1.3628(16) . ? C3 C4 1.3882(19) . ? C4 C5 1.395(2) . ? C4 H4 0.9500 . ? C5 C6 1.3842(19) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.2369(16) . ? C7 O1 1.3106(15) . ? C8 O4 1.2012(18) . ? C8 O3 1.3701(17) . ? C8 C9 1.492(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O5 1.4350(16) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O1 H1 0.8400 . ? 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 118.52(12) . . ? C2 C1 C7 122.22(12) . . ? C6 C1 C7 119.25(11) . . ? C1 C2 O3 122.13(11) . . ? C1 C2 C3 121.40(12) . . ? O3 C2 C3 116.43(11) . . ? O5 C3 C4 125.43(12) . . ? O5 C3 C2 115.18(11) . . ? C4 C3 C2 119.39(12) . . ? C3 C4 C5 119.55(12) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.89(13) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.22(12) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 O1 123.05(11) . . ? O2 C7 C1 123.17(11) . . ? O1 C7 C1 113.77(11) . . ? O4 C8 O3 122.69(12) . . ? O4 C8 C9 126.96(14) . . ? O3 C8 C9 110.36(13) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 O1 H1 109.5 . . ? C8 O3 C2 116.24(10) . . ? C3 O5 C10 116.93(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O3 -177.86(11) . . . . ? C7 C1 C2 O3 3.78(19) . . . . ? C6 C1 C2 C3 -0.16(19) . . . . ? C7 C1 C2 C3 -178.52(11) . . . . ? C1 C2 C3 O5 -178.76(11) . . . . ? O3 C2 C3 O5 -0.93(17) . . . . ? C1 C2 C3 C4 1.6(2) . . . . ? O3 C2 C3 C4 179.46(11) . . . . ? O5 C3 C4 C5 179.06(12) . . . . ? C2 C3 C4 C5 -1.4(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C1 1.8(2) . . . . ? C2 C1 C6 C5 -1.57(19) . . . . ? C7 C1 C6 C5 176.84(12) . . . . ? C2 C1 C7 O2 2.1(2) . . . . ? C6 C1 C7 O2 -176.21(12) . . . . ? C2 C1 C7 O1 -179.24(12) . . . . ? C6 C1 C7 O1 2.41(17) . . . . ? O4 C8 O3 C2 -2.19(18) . . . . ? C9 C8 O3 C2 177.60(11) . . . . ? C1 C2 O3 C8 -83.18(15) . . . . ? C3 C2 O3 C8 99.01(13) . . . . ? C4 C3 O5 C10 2.88(19) . . . . ? C2 C3 O5 C10 -176.69(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.81 2.6474(13) 173.1 3_755 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.243 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.047 data_4-fluoroaspirin _database_code_depnum_ccdc_archive 'CCDC 800302' #TrackingRef '- Aspirin derivatives paper 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-4-fluorobenzoic acid' ; _chemical_name_common 4-fluoroaspirin _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 F O4' _chemical_formula_sum 'C9 H7 F O4' _chemical_formula_weight 198.15 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.90840(10) _cell_length_b 10.0101(5) _cell_length_c 17.4781(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.917(3) _cell_angle_gamma 90.00 _cell_volume 852.51(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17077 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10471 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1959 _reflns_number_gt 1483 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0509P)^2^+0.2128P] 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 1959 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.7822(3) 0.57500(17) 0.67296(9) 0.0274(4) Uani 1 1 d . . . C2 C 0.5662(3) 0.66158(17) 0.68279(10) 0.0274(4) Uani 1 1 d . . . C3 C 0.5127(3) 0.70334(18) 0.75474(10) 0.0317(4) Uani 1 1 d . . . H3 H 0.3675 0.7639 0.7604 0.038 Uiso 1 1 calc R . . C4 C 0.6763(3) 0.65434(19) 0.81790(10) 0.0324(4) Uani 1 1 d . . . C5 C 0.8859(3) 0.56573(18) 0.81222(10) 0.0330(4) Uani 1 1 d . . . H5 H 0.9929 0.5323 0.8570 0.040 Uiso 1 1 calc R . . C6 C 0.9372(3) 0.52646(18) 0.73955(10) 0.0298(4) Uani 1 1 d . . . H6 H 1.0814 0.4649 0.7347 0.036 Uiso 1 1 calc R . . C7 C 0.8591(3) 0.53809(17) 0.59617(10) 0.0290(4) Uani 1 1 d . . . C8 C 0.4445(3) 0.81665(17) 0.58335(10) 0.0288(4) Uani 1 1 d . . . C9 C 0.2379(3) 0.84336(19) 0.51604(10) 0.0331(4) Uani 1 1 d . . . H9A H 0.2515 0.7748 0.4767 0.050 Uiso 1 1 calc R . . H9B H 0.2720 0.9315 0.4947 0.050 Uiso 1 1 calc R . . H9C H 0.0537 0.8415 0.5323 0.050 Uiso 1 1 calc R . . O1 O 1.0363(3) 0.43982(13) 0.59843(8) 0.0366(3) Uani 1 1 d . . . O2 O 0.7708(2) 0.59720(12) 0.53655(7) 0.0333(3) Uani 1 1 d . . . O3 O 0.3821(2) 0.70234(12) 0.61978(7) 0.0303(3) Uani 1 1 d . . . O4 O 0.6417(2) 0.88315(12) 0.60581(7) 0.0365(3) Uani 1 1 d . . . F1 F 0.6237(2) 0.69430(12) 0.88850(6) 0.0414(3) Uani 1 1 d . . . H1A H 1.108(6) 0.436(3) 0.5517(19) 0.089(10) 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 0.0283(8) 0.0252(9) 0.0289(9) 0.0014(7) 0.0035(7) -0.0038(6) C2 0.0252(8) 0.0264(9) 0.0301(9) 0.0048(7) 0.0014(6) -0.0042(6) C3 0.0286(9) 0.0295(10) 0.0382(10) 0.0024(7) 0.0091(7) -0.0007(7) C4 0.0351(9) 0.0358(10) 0.0277(9) -0.0002(7) 0.0092(7) -0.0076(7) C5 0.0310(9) 0.0360(10) 0.0314(10) 0.0064(7) 0.0013(7) -0.0034(7) C6 0.0277(8) 0.0280(9) 0.0334(10) 0.0021(7) 0.0032(7) -0.0006(7) C7 0.0298(8) 0.0240(9) 0.0325(10) -0.0016(7) 0.0013(7) -0.0017(7) C8 0.0286(9) 0.0277(9) 0.0316(9) 0.0000(7) 0.0093(7) -0.0006(7) C9 0.0315(9) 0.0354(10) 0.0327(10) 0.0058(8) 0.0049(7) 0.0012(7) O1 0.0454(8) 0.0300(7) 0.0348(7) 0.0005(6) 0.0066(6) 0.0084(5) O2 0.0378(7) 0.0329(7) 0.0284(7) 0.0000(5) 0.0007(5) 0.0034(5) O3 0.0260(6) 0.0311(7) 0.0331(7) 0.0072(5) 0.0006(5) -0.0009(5) O4 0.0355(7) 0.0317(7) 0.0416(8) 0.0035(6) 0.0023(5) -0.0067(5) F1 0.0472(6) 0.0493(7) 0.0298(6) -0.0012(5) 0.0139(5) -0.0033(5) _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 C2 1.396(2) . ? C1 C6 1.399(2) . ? C1 C7 1.484(2) . ? C2 C3 1.380(2) . ? C2 O3 1.3988(19) . ? C3 C4 1.375(2) . ? C3 H3 0.9500 . ? C4 F1 1.351(2) . ? C4 C5 1.371(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.231(2) . ? C7 O1 1.310(2) . ? C8 O4 1.201(2) . ? C8 O3 1.362(2) . ? C8 C9 1.482(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 H1A 0.93(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 117.28(15) . . ? C2 C1 C7 123.07(15) . . ? C6 C1 C7 119.60(16) . . ? C3 C2 C1 122.08(15) . . ? C3 C2 O3 116.94(15) . . ? C1 C2 O3 120.83(15) . . ? C4 C3 C2 117.80(16) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? F1 C4 C5 119.02(15) . . ? F1 C4 C3 118.04(16) . . ? C5 C4 C3 122.93(16) . . ? C4 C5 C6 118.17(16) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C5 C6 C1 121.69(16) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O2 C7 O1 123.45(16) . . ? O2 C7 C1 122.95(16) . . ? O1 C7 C1 113.57(15) . . ? O4 C8 O3 122.03(16) . . ? O4 C8 C9 127.36(16) . . ? O3 C8 C9 110.61(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 O1 H1A 108.9(18) . . ? C8 O3 C2 116.93(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.9(2) . . . . ? C7 C1 C2 C3 -174.46(15) . . . . ? C6 C1 C2 O3 -172.57(14) . . . . ? C7 C1 C2 O3 10.1(2) . . . . ? C1 C2 C3 C4 -1.5(3) . . . . ? O3 C2 C3 C4 174.12(14) . . . . ? C2 C3 C4 F1 -179.62(14) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? F1 C4 C5 C6 -179.77(15) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? C7 C1 C6 C5 175.22(15) . . . . ? C2 C1 C7 O2 12.6(3) . . . . ? C6 C1 C7 O2 -164.67(16) . . . . ? C2 C1 C7 O1 -169.52(15) . . . . ? C6 C1 C7 O1 13.2(2) . . . . ? O4 C8 O3 C2 -3.1(2) . . . . ? C9 C8 O3 C2 177.45(14) . . . . ? C3 C2 O3 C8 93.21(18) . . . . ? C1 C2 O3 C8 -91.15(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O2 0.93(3) 1.75(3) 2.6717(18) 171(3) 3_766 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.183 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.055 data_4-methoxyaspirin _database_code_depnum_ccdc_archive 'CCDC 800303' #TrackingRef '- Aspirin derivatives paper 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-4-methoxybenzoic acid' ; _chemical_name_common 4-methoxyaspirin _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O5' _chemical_formula_sum 'C10 H10 O5' _chemical_formula_weight 210.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 5.06880(10) _cell_length_b 9.4619(3) _cell_length_c 20.0281(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.069(2) _cell_angle_gamma 90.00 _cell_volume 958.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11477 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19382 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2193 _reflns_number_gt 1733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0511P)^2^+0.8521P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2193 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.1493(4) 0.9516(2) 0.85120(9) 0.0231(4) Uani 1 1 d . . . C2 C -0.0686(4) 0.8627(2) 0.83762(10) 0.0233(4) Uani 1 1 d . . . C3 C -0.1760(4) 0.8398(2) 0.77294(10) 0.0256(4) Uani 1 1 d . . . H3 H -0.3214 0.7773 0.7648 0.031 Uiso 1 1 calc R . . C4 C -0.0684(4) 0.9094(2) 0.71992(10) 0.0247(4) Uani 1 1 d . . . C5 C 0.1418(4) 1.0035(2) 0.73216(10) 0.0268(4) Uani 1 1 d . . . H5 H 0.2103 1.0542 0.6963 0.032 Uiso 1 1 calc R . . C6 C 0.2485(4) 1.0224(2) 0.79648(10) 0.0253(4) Uani 1 1 d . . . H6 H 0.3938 1.0851 0.8043 0.030 Uiso 1 1 calc R . . C7 C 0.2841(4) 0.9761(2) 0.91811(10) 0.0253(4) Uani 1 1 d . . . C8 C -0.1151(4) 0.6805(2) 0.91753(10) 0.0235(4) Uani 1 1 d . . . C9 C -0.2891(4) 0.6358(2) 0.97082(11) 0.0302(5) Uani 1 1 d . . . H9A H -0.2161 0.5506 0.9930 0.045 Uiso 1 1 calc R . . H9B H -0.4670 0.6156 0.9506 0.045 Uiso 1 1 calc R . . H9C H -0.2985 0.7118 1.0038 0.045 Uiso 1 1 calc R . . C10 C -0.3639(4) 0.7979(2) 0.63812(11) 0.0355(5) Uani 1 1 d . . . H10A H -0.5229 0.8298 0.6588 0.053 Uiso 1 1 calc R . . H10B H -0.3147 0.7035 0.6548 0.053 Uiso 1 1 calc R . . H10C H -0.3995 0.7944 0.5894 0.053 Uiso 1 1 calc R . . O1 O 0.4612(3) 1.06993(16) 0.92386(7) 0.0351(4) Uani 1 1 d . . . O2 O 0.2190(3) 0.90023(16) 0.96761(7) 0.0311(4) Uani 1 1 d . . . H2 H 0.3272 0.9139 1.0007 0.047 Uiso 1 1 calc R . . O3 O -0.2081(3) 0.80335(15) 0.88864(7) 0.0279(3) Uani 1 1 d . . . O4 O 0.0774(3) 0.62113(15) 0.90016(7) 0.0284(3) Uani 1 1 d . . . O5 O -0.1529(3) 0.89382(17) 0.65447(7) 0.0341(4) 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 0.0259(9) 0.0204(9) 0.0232(9) 0.0009(8) 0.0027(7) 0.0023(8) C2 0.0229(9) 0.0202(9) 0.0272(10) 0.0059(8) 0.0039(8) 0.0026(7) C3 0.0214(9) 0.0217(10) 0.0332(11) 0.0023(8) -0.0012(8) 0.0005(7) C4 0.0251(9) 0.0245(10) 0.0240(10) 0.0025(8) -0.0013(8) 0.0061(8) C5 0.0284(10) 0.0265(10) 0.0262(10) 0.0052(8) 0.0058(8) 0.0016(8) C6 0.0251(9) 0.0232(10) 0.0279(10) 0.0015(8) 0.0035(8) -0.0004(8) C7 0.0302(10) 0.0199(9) 0.0260(10) -0.0005(8) 0.0044(8) -0.0015(8) C8 0.0218(9) 0.0231(9) 0.0252(9) -0.0009(8) -0.0021(7) -0.0008(8) C9 0.0269(10) 0.0337(11) 0.0302(11) 0.0075(9) 0.0030(8) 0.0019(9) C10 0.0337(11) 0.0347(12) 0.0370(12) 0.0002(10) -0.0041(9) 0.0016(9) O1 0.0453(9) 0.0285(8) 0.0309(8) -0.0001(6) -0.0019(7) -0.0127(7) O2 0.0403(8) 0.0308(8) 0.0220(7) 0.0010(6) 0.0008(6) -0.0073(7) O3 0.0250(7) 0.0269(8) 0.0324(8) 0.0087(6) 0.0053(6) 0.0008(6) O4 0.0273(7) 0.0267(7) 0.0314(8) 0.0001(6) 0.0033(6) 0.0030(6) O5 0.0360(8) 0.0376(9) 0.0274(8) 0.0018(6) -0.0061(6) -0.0010(7) _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 1.400(3) . ? C1 C6 1.407(3) . ? C1 C7 1.479(3) . ? C2 C3 1.386(3) . ? C2 O3 1.401(2) . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 O5 1.358(2) . ? C4 C5 1.397(3) . ? C5 C6 1.373(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.262(2) . ? C7 O2 1.286(2) . ? C8 O4 1.199(2) . ? C8 O3 1.367(2) . ? C8 C9 1.493(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O5 1.423(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O2 H2 0.8400 . ? 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 117.10(18) . . ? C2 C1 C7 125.29(17) . . ? C6 C1 C7 117.61(18) . . ? C3 C2 C1 121.83(17) . . ? C3 C2 O3 115.74(17) . . ? C1 C2 O3 122.10(17) . . ? C2 C3 C4 119.32(18) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? O5 C4 C3 124.81(18) . . ? O5 C4 C5 115.01(17) . . ? C3 C4 C5 120.17(18) . . ? C6 C5 C4 119.48(18) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 122.00(19) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? O1 C7 O2 122.84(18) . . ? O1 C7 C1 118.20(17) . . ? O2 C7 C1 118.95(17) . . ? O4 C8 O3 122.61(18) . . ? O4 C8 C9 127.51(19) . . ? O3 C8 C9 109.87(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 O2 H2 109.5 . . ? C8 O3 C2 118.21(15) . . ? C4 O5 C10 118.15(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.8(3) . . . . ? C7 C1 C2 C3 -176.70(18) . . . . ? C6 C1 C2 O3 -170.40(17) . . . . ? C7 C1 C2 O3 10.1(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? O3 C2 C3 C4 172.18(17) . . . . ? C2 C3 C4 O5 178.80(18) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? O5 C4 C5 C6 -177.45(18) . . . . ? C3 C4 C5 C6 2.8(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? C7 C1 C6 C5 178.11(19) . . . . ? C2 C1 C7 O1 -172.98(19) . . . . ? C6 C1 C7 O1 7.5(3) . . . . ? C2 C1 C7 O2 7.8(3) . . . . ? C6 C1 C7 O2 -171.63(18) . . . . ? O4 C8 O3 C2 -1.2(3) . . . . ? C9 C8 O3 C2 179.49(16) . . . . ? C3 C2 O3 C8 101.5(2) . . . . ? C1 C2 O3 C8 -84.9(2) . . . . ? C3 C4 O5 C10 -1.1(3) . . . . ? C5 C4 O5 C10 179.09(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.84 1.80 2.633(2) 174.0 3_677 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.391 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.059 data_5-methoxyaspirin _database_code_depnum_ccdc_archive 'CCDC 800304' #TrackingRef '- Aspirin derivatives paper 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-methoxybenzoic acid' ; _chemical_name_common 5-methoxyaspirin _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O5' _chemical_formula_sum 'C10 H10 O5' _chemical_formula_weight 210.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.03850(10) _cell_length_b 17.3609(5) _cell_length_c 10.8931(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.402(2) _cell_angle_gamma 90.00 _cell_volume 948.62(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6304 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9317 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12672 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2164 _reflns_number_gt 1889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0418P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2164 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.0232(2) 0.42118(7) 0.67991(11) 0.0128(2) Uani 1 1 d . . . C2 C 0.2002(2) 0.36911(7) 0.63229(10) 0.0129(2) Uani 1 1 d . . . C3 C 0.4043(2) 0.33598(7) 0.70773(11) 0.0144(3) Uani 1 1 d . . . H3 H 0.5234 0.3012 0.6738 0.017 Uiso 1 1 calc R . . C4 C 0.4374(2) 0.35301(7) 0.83325(11) 0.0151(3) Uani 1 1 d . . . H4 H 0.5765 0.3295 0.8851 0.018 Uiso 1 1 calc R . . C5 C 0.2641(2) 0.40498(7) 0.88180(11) 0.0145(3) Uani 1 1 d . . . C6 C 0.0581(2) 0.43880(7) 0.80526(11) 0.0144(3) Uani 1 1 d . . . H6 H -0.0592 0.4742 0.8390 0.017 Uiso 1 1 calc R . . C7 C -0.1996(2) 0.45760(7) 0.60039(11) 0.0128(2) Uani 1 1 d . . . C8 C 0.0023(2) 0.30411(7) 0.45686(12) 0.0172(3) Uani 1 1 d . . . C9 C -0.0213(3) 0.30775(9) 0.31910(12) 0.0263(3) Uani 1 1 d . . . H9A H -0.0856 0.2581 0.2852 0.039 Uiso 1 1 calc R . . H9B H 0.1536 0.3191 0.2910 0.039 Uiso 1 1 calc R . . H9C H -0.1476 0.3484 0.2909 0.039 Uiso 1 1 calc R . . C10 C 0.4944(3) 0.39487(9) 1.08237(12) 0.0242(3) Uani 1 1 d . . . H10A H 0.4762 0.3387 1.0848 0.036 Uiso 1 1 calc R . . H10B H 0.4896 0.4158 1.1657 0.036 Uiso 1 1 calc R . . H10C H 0.6644 0.4083 1.0510 0.036 Uiso 1 1 calc R . . O1 O -0.33158(17) 0.50997(5) 0.65758(8) 0.0166(2) Uani 1 1 d . . . H1 H -0.4563 0.5275 0.6090 0.025 Uiso 1 1 calc R . . O2 O -0.25703(17) 0.43995(5) 0.49201(8) 0.0167(2) Uani 1 1 d . . . O3 O 0.19087(16) 0.35464(5) 0.50551(7) 0.0148(2) Uani 1 1 d . . . O4 O -0.1232(2) 0.26328(6) 0.51924(9) 0.0251(2) Uani 1 1 d . . . O5 O 0.27922(19) 0.42680(6) 1.00282(8) 0.0200(2) 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 0.0125(5) 0.0129(6) 0.0128(6) 0.0017(4) -0.0004(4) -0.0014(4) C2 0.0137(6) 0.0141(6) 0.0107(6) 0.0000(4) 0.0006(4) -0.0026(4) C3 0.0132(5) 0.0139(6) 0.0162(6) -0.0006(4) 0.0015(4) 0.0006(4) C4 0.0140(6) 0.0154(6) 0.0153(6) 0.0020(5) -0.0025(4) 0.0009(4) C5 0.0169(6) 0.0153(6) 0.0110(6) -0.0004(4) -0.0007(4) -0.0009(5) C6 0.0143(6) 0.0146(6) 0.0141(6) -0.0008(4) 0.0007(4) 0.0009(4) C7 0.0123(5) 0.0121(6) 0.0141(6) 0.0009(4) 0.0018(4) -0.0016(4) C8 0.0178(6) 0.0161(6) 0.0174(6) -0.0040(5) -0.0006(5) 0.0019(5) C9 0.0338(8) 0.0295(8) 0.0145(6) -0.0051(5) -0.0028(5) 0.0026(6) C10 0.0287(7) 0.0288(7) 0.0135(6) -0.0017(5) -0.0065(5) 0.0106(6) O1 0.0173(4) 0.0180(5) 0.0139(4) -0.0007(3) -0.0025(3) 0.0059(3) O2 0.0163(4) 0.0202(5) 0.0129(4) -0.0017(3) -0.0028(3) 0.0031(3) O3 0.0148(4) 0.0189(5) 0.0106(4) -0.0010(3) 0.0004(3) -0.0008(3) O4 0.0301(5) 0.0228(5) 0.0223(5) -0.0023(4) 0.0021(4) -0.0093(4) O5 0.0233(5) 0.0246(5) 0.0110(5) -0.0022(4) -0.0043(4) 0.0082(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 C6 1.3942(17) . ? C1 C2 1.4029(17) . ? C1 C7 1.4924(16) . ? C2 C3 1.3802(17) . ? C2 O3 1.4001(14) . ? C3 C4 1.3934(17) . ? C3 H3 0.9500 . ? C4 C5 1.3940(17) . ? C4 H4 0.9500 . ? C5 O5 1.3668(14) . ? C5 C6 1.3979(17) . ? C6 H6 0.9500 . ? C7 O2 1.2277(15) . ? C7 O1 1.3173(15) . ? C8 O4 1.2022(16) . ? C8 O3 1.3631(15) . ? C8 C9 1.4954(18) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O5 1.4341(15) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O1 H1 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.53(11) . . ? C6 C1 C7 119.61(11) . . ? C2 C1 C7 121.86(11) . . ? C3 C2 O3 117.80(11) . . ? C3 C2 C1 120.81(11) . . ? O3 C2 C1 121.13(10) . . ? C2 C3 C4 120.63(11) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.22(11) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? O5 C5 C4 124.43(11) . . ? O5 C5 C6 115.45(11) . . ? C4 C5 C6 120.13(11) . . ? C1 C6 C5 120.67(11) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O2 C7 O1 122.90(11) . . ? O2 C7 C1 123.29(11) . . ? O1 C7 C1 113.80(10) . . ? O4 C8 O3 122.97(12) . . ? O4 C8 C9 126.56(12) . . ? O3 C8 C9 110.47(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 O1 H1 109.5 . . ? C8 O3 C2 117.15(9) . . ? C5 O5 C10 116.48(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.82 2.6593(12) 175.7 3_466 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.325 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.049 data_6-fluoroaspirin _database_code_depnum_ccdc_archive 'CCDC 800305' #TrackingRef '- Aspirin derivatives paper 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-6-fluorobenzoic acid' ; _chemical_name_common 6-fluoroaspirin _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 F O4' _chemical_formula_sum 'C9 H7 F O4' _chemical_formula_weight 198.15 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3711(2) _cell_length_b 7.09520(10) _cell_length_c 16.7141(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.9190(10) _cell_angle_gamma 90.00 _cell_volume 858.31(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12478 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9375 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1966 _reflns_number_gt 1770 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0307P)^2^+0.6335P] 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 1966 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 H4 H 0.752(2) 0.153(3) 0.5097(10) 0.023(4) Uiso 1 1 d . . . H3 H 0.971(2) 0.385(2) 0.5643(10) 0.021(4) Uiso 1 1 d . . . H5 H 0.445(3) 0.175(3) 0.5362(11) 0.029(5) Uiso 1 1 d . . . H9B H 1.027(3) 1.023(3) 0.6907(12) 0.038(5) Uiso 1 1 d . . . H9A H 1.193(3) 0.890(3) 0.6922(12) 0.040(6) Uiso 1 1 d . . . H9C H 1.139(3) 1.036(3) 0.6217(12) 0.036(5) Uiso 1 1 d . . . H1A H 0.581(3) 0.950(3) 0.7065(14) 0.051(6) Uiso 1 1 d . . . F1 F 0.31923(11) 0.41680(13) 0.62062(5) 0.0239(2) Uani 1 1 d . . . O2 O 0.47343(15) 0.66628(14) 0.74431(6) 0.0211(2) Uani 1 1 d . . . O3 O 0.92809(13) 0.66489(14) 0.65776(6) 0.0181(2) Uani 1 1 d . . . O4 O 0.89298(14) 0.82147(15) 0.53840(6) 0.0214(2) Uani 1 1 d . . . O1 O 0.61453(16) 0.86784(15) 0.67369(7) 0.0240(3) Uani 1 1 d . . . C7 C 0.56193(19) 0.69761(19) 0.69114(8) 0.0171(3) Uani 1 1 d . . . C8 C 0.96251(19) 0.81179(19) 0.60913(8) 0.0167(3) Uani 1 1 d . . . C1 C 0.61772(19) 0.54706(19) 0.63847(8) 0.0155(3) Uani 1 1 d . . . C2 C 0.79547(18) 0.53452(19) 0.62106(8) 0.0159(3) Uani 1 1 d . . . C4 C 0.7153(2) 0.2565(2) 0.54196(8) 0.0199(3) Uani 1 1 d . . . C5 C 0.5365(2) 0.2649(2) 0.55682(8) 0.0196(3) Uani 1 1 d . . . C3 C 0.8463(2) 0.3907(2) 0.57427(8) 0.0185(3) Uani 1 1 d . . . C6 C 0.49289(19) 0.4081(2) 0.60540(8) 0.0175(3) Uani 1 1 d . . . C9 C 1.0918(2) 0.9498(2) 0.65718(10) 0.0235(3) 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 F1 0.0157(4) 0.0293(5) 0.0274(4) -0.0029(4) 0.0060(3) -0.0032(3) O2 0.0263(6) 0.0177(5) 0.0225(5) -0.0004(4) 0.0128(4) -0.0003(4) O3 0.0183(5) 0.0184(5) 0.0171(5) 0.0000(4) 0.0020(4) -0.0031(4) O4 0.0241(5) 0.0218(5) 0.0185(5) 0.0001(4) 0.0046(4) -0.0026(4) O1 0.0341(6) 0.0142(5) 0.0285(6) -0.0013(4) 0.0177(5) -0.0001(4) C7 0.0179(6) 0.0159(6) 0.0173(6) 0.0010(5) 0.0032(5) 0.0013(5) C8 0.0144(6) 0.0163(6) 0.0208(7) -0.0009(5) 0.0071(5) 0.0011(5) C1 0.0188(7) 0.0145(6) 0.0135(6) 0.0024(5) 0.0038(5) 0.0011(5) C2 0.0157(6) 0.0159(6) 0.0155(6) 0.0022(5) 0.0019(5) -0.0013(5) C4 0.0261(8) 0.0161(6) 0.0185(6) -0.0007(5) 0.0064(5) 0.0021(6) C5 0.0237(7) 0.0163(6) 0.0182(6) 0.0003(5) 0.0027(5) -0.0033(6) C3 0.0192(7) 0.0181(7) 0.0190(6) 0.0008(5) 0.0060(5) 0.0016(5) C6 0.0150(6) 0.0203(7) 0.0175(6) 0.0035(5) 0.0039(5) 0.0001(5) C9 0.0226(8) 0.0212(7) 0.0259(7) -0.0021(6) 0.0027(6) -0.0049(6) _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 F1 C6 1.3529(16) . ? O2 C7 1.2183(17) . ? O3 C8 1.3745(16) . ? O3 C2 1.4001(16) . ? O4 C8 1.1981(17) . ? O1 C7 1.3180(17) . ? O1 H1A 0.87(2) . ? C7 C1 1.4908(18) . ? C8 C9 1.491(2) . ? C1 C6 1.3896(19) . ? C1 C2 1.3977(19) . ? C2 C3 1.3800(19) . ? C4 C5 1.388(2) . ? C4 C3 1.391(2) . ? C4 H4 0.980(18) . ? C5 C6 1.377(2) . ? C5 H5 0.943(19) . ? C3 H3 0.968(18) . ? C9 H9B 0.96(2) . ? C9 H9A 0.95(2) . ? C9 H9C 0.96(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 C8 O3 C2 115.70(10) . . ? C7 O1 H1A 110.2(15) . . ? O2 C7 O1 123.31(13) . . ? O2 C7 C1 123.08(12) . . ? O1 C7 C1 113.60(12) . . ? O4 C8 O3 122.31(13) . . ? O4 C8 C9 127.16(13) . . ? O3 C8 C9 110.52(12) . . ? C6 C1 C2 116.63(12) . . ? C6 C1 C7 120.47(12) . . ? C2 C1 C7 122.88(12) . . ? C3 C2 C1 122.07(13) . . ? C3 C2 O3 119.65(12) . . ? C1 C2 O3 118.10(12) . . ? C5 C4 C3 120.98(13) . . ? C5 C4 H4 120.1(10) . . ? C3 C4 H4 118.9(10) . . ? C6 C5 C4 118.21(13) . . ? C6 C5 H5 119.0(11) . . ? C4 C5 H5 122.7(11) . . ? C2 C3 C4 118.88(13) . . ? C2 C3 H3 120.0(10) . . ? C4 C3 H3 121.2(10) . . ? F1 C6 C5 118.65(12) . . ? F1 C6 C1 118.15(12) . . ? C5 C6 C1 123.19(13) . . ? C8 C9 H9B 109.4(12) . . ? C8 C9 H9A 112.5(13) . . ? H9B C9 H9A 107.6(17) . . ? C8 C9 H9C 110.8(12) . . ? H9B C9 H9C 106.9(17) . . ? H9A C9 H9C 109.3(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O2 0.87(2) 1.82(2) 2.6682(14) 165(2) 2_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.302 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.054