# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Mike Hursthouse' _publ_contact_author_email MBH@SOTON.AC.UK _publ_section_title ; Intriguing Relationships and Associations in the Crystal Structures of a Family of Substituted Aspirin Molecules ; loop_ _publ_author_name 'Mike Hursthouse' 'Riccardo Montis' 'Graham J Tizzard' # Attachment 'Asp_derivatives.cif' data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 643150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-4-methylbenzoic acid' ; _chemical_name_common "'2-acetyloxy-4-methylbenzoic acid'" _chemical_melting_point 135 _chemical_formula_moiety 'C10 H10 O4' _chemical_formula_sum 'C10 H10 O4' _chemical_formula_weight 194.18 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 _symmetry_space_group_name_Hall -P2yn 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 4.6363(3) _cell_length_b 10.3293(9) _cell_length_c 19.5855(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.632(5) _cell_angle_gamma 90.00 _cell_volume 936.06(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10270 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; 'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.552476' ; _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 95mm 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 10687 _diffrn_reflns_av_R_equivalents 0.1204 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2133 _reflns_number_gt 1257 _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 ? _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^)+(0.0671P)^2^+0.3109P] 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 2133 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1242 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.6239(5) 0.9334(2) 0.84940(13) 0.0311(6) Uani 1 1 d . . . C2 C 0.4038(5) 0.8426(3) 0.84051(13) 0.0327(6) Uani 1 1 d . . . C3 C 0.2850(6) 0.8091(3) 0.77632(15) 0.0410(7) Uani 1 1 d . . . H3 H 0.1378 0.7451 0.7720 0.049 Uiso 1 1 calc R . . C4 C 0.3799(6) 0.8686(3) 0.71806(15) 0.0442(8) Uani 1 1 d . . . C5 C 0.5912(6) 0.9629(3) 0.72632(14) 0.0449(8) Uani 1 1 d . . . H5 H 0.6541 1.0066 0.6873 0.054 Uiso 1 1 calc R . . C6 C 0.7129(6) 0.9947(3) 0.79072(14) 0.0390(7) Uani 1 1 d . . . H6 H 0.8590 1.0592 0.7950 0.047 Uiso 1 1 calc R . . C7 C 0.7723(5) 0.9654(2) 0.91652(13) 0.0313(6) Uani 1 1 d . . . C8 C 0.3864(6) 0.6839(2) 0.92732(15) 0.0359(6) Uani 1 1 d . . . C9 C 0.2367(6) 0.6550(3) 0.99097(15) 0.0424(7) Uani 1 1 d . . . H9A H 0.3056 0.5719 1.0099 0.064 Uiso 1 1 calc R . . H9B H 0.0277 0.6504 0.9801 0.064 Uiso 1 1 calc R . . H9C H 0.2788 0.7237 1.0247 0.064 Uiso 1 1 calc R . . C10 C 0.2457(8) 0.8315(4) 0.64851(15) 0.0603(10) Uani 1 1 d . . . H10A H 0.3690 0.8620 0.6130 0.090 Uiso 1 1 calc R . . H10B H 0.0542 0.8714 0.6417 0.090 Uiso 1 1 calc R . . H10C H 0.2269 0.7372 0.6457 0.090 Uiso 1 1 calc R . . O1 O 0.9530(4) 1.05832(18) 0.91760(10) 0.0411(5) Uani 1 1 d . . . H1 H 1.0488 1.0592 0.9555 0.062 Uiso 1 1 calc R . . O2 O 0.7204(4) 0.90000(17) 0.96920(9) 0.0361(5) Uani 1 1 d . . . O3 O 0.2703(4) 0.79215(17) 0.89704(9) 0.0353(5) Uani 1 1 d . . . O4 O 0.5805(4) 0.62434(18) 0.90396(10) 0.0450(6) 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 0.0296(13) 0.0292(13) 0.0349(15) -0.0002(11) 0.0054(10) 0.0066(11) C2 0.0320(13) 0.0292(14) 0.0369(15) 0.0012(11) 0.0030(11) 0.0091(11) C3 0.0379(16) 0.0343(16) 0.0496(18) -0.0053(13) -0.0053(13) 0.0114(12) C4 0.0440(17) 0.0460(18) 0.0422(17) -0.0049(14) -0.0012(13) 0.0237(14) C5 0.0444(17) 0.0552(19) 0.0364(17) 0.0090(14) 0.0118(13) 0.0221(15) C6 0.0352(15) 0.0408(17) 0.0418(18) 0.0018(13) 0.0085(12) 0.0046(12) C7 0.0307(13) 0.0239(13) 0.0405(16) -0.0003(12) 0.0117(11) 0.0040(11) C8 0.0343(14) 0.0248(14) 0.0469(17) -0.0032(12) -0.0119(12) 0.0017(12) C9 0.0349(15) 0.0366(16) 0.0550(19) 0.0111(14) -0.0029(13) -0.0015(12) C10 0.079(2) 0.062(2) 0.0381(18) -0.0093(16) -0.0093(16) 0.0338(19) O1 0.0478(12) 0.0315(10) 0.0435(12) 0.0026(9) 0.0007(9) -0.0088(9) O2 0.0428(11) 0.0331(10) 0.0331(11) -0.0005(8) 0.0087(8) -0.0040(8) O3 0.0293(10) 0.0296(10) 0.0472(11) 0.0075(8) 0.0024(8) 0.0027(7) O4 0.0504(13) 0.0335(11) 0.0498(13) -0.0066(9) -0.0063(10) 0.0122(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.388(4) . ? C1 C6 1.397(4) . ? C1 C7 1.482(4) . ? C2 C3 1.384(4) . ? C2 O3 1.403(3) . ? C3 C4 1.392(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 C10 1.511(4) . ? C5 C6 1.388(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.269(3) . ? C7 O1 1.273(3) . ? C8 O4 1.204(3) . ? C8 O3 1.360(3) . ? C8 C9 1.495(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 117.1(2) . . ? C2 C1 C7 123.9(2) . . ? C6 C1 C7 118.9(2) . . ? C3 C2 C1 122.0(3) . . ? C3 C2 O3 117.0(2) . . ? C1 C2 O3 120.6(2) . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 C10 122.2(3) . . ? C3 C4 C10 119.6(3) . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O2 C7 O1 123.1(2) . . ? O2 C7 C1 120.1(2) . . ? O1 C7 C1 116.8(2) . . ? O4 C8 O3 122.6(3) . . ? O4 C8 C9 127.7(3) . . ? O3 C8 C9 109.6(2) . . ? 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 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 O1 H1 109.5 . . ? C8 O3 C2 117.8(2) . . ? 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 2.640(3) 166.2 3_777 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.269 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.066 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 643151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-bromobenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-bromobenzoic acid'" _chemical_melting_point 160 _chemical_formula_moiety 'C9 H7 Br O4' _chemical_formula_sum 'C9 H7 Br O4' _chemical_formula_weight 259.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 10.3912(4) _cell_length_b 4.72650(10) _cell_length_c 19.5116(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.383(2) _cell_angle_gamma 90.00 _cell_volume 952.35(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2366 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.88 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 4.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1665 _exptl_absorpt_correction_T_max 0.7248 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _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 95mm 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 10114 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2171 _reflns_number_gt 1619 _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 ? _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^)+(0.0242P)^2^+1.1431P] 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 2171 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0757 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.89296(3) 0.24254(7) 0.089926(16) 0.02812(11) Uani 1 1 d . . . O1 O 1.50444(18) 0.2920(4) 0.06212(10) 0.0194(4) Uani 1 1 d . . . H1 H 1.5522 0.1803 0.0430 0.029 Uiso 1 1 calc R . . O2 O 1.34713(18) 0.0582(4) -0.00210(10) 0.0227(5) Uani 1 1 d . . . O3 O 1.43271(18) 0.7316(4) 0.13639(10) 0.0210(4) Uani 1 1 d . . . O4 O 1.5091(2) 0.4299(5) 0.22034(11) 0.0314(5) Uani 1 1 d . . . C1 C 1.2859(3) 0.3749(6) 0.08204(14) 0.0171(6) Uani 1 1 d . . . C2 C 1.3122(3) 0.5953(6) 0.12949(14) 0.0197(6) Uani 1 1 d . . . C7 C 1.3829(3) 0.2294(6) 0.04338(13) 0.0173(5) Uani 1 1 d . . . C4 C 1.0923(3) 0.5974(6) 0.15590(15) 0.0249(7) Uani 1 1 d . . . H4 H 1.0270 0.6693 0.1815 0.030 Uiso 1 1 calc R . . C3 C 1.2173(3) 0.7028(6) 0.16649(16) 0.0243(7) Uani 1 1 d . . . H3 H 1.2379 0.8492 0.1993 0.029 Uiso 1 1 calc R . . C5 C 1.0638(3) 0.3863(6) 0.10748(15) 0.0204(6) Uani 1 1 d . . . C6 C 1.1590(3) 0.2751(6) 0.07096(14) 0.0177(6) Uani 1 1 d . . . H6 H 1.1376 0.1296 0.0381 0.021 Uiso 1 1 calc R . . C8 C 1.5276(3) 0.6261(6) 0.18358(15) 0.0207(6) Uani 1 1 d . . . C9 C 1.6505(3) 0.7853(6) 0.18047(17) 0.0279(7) Uani 1 1 d . . . H9A H 1.7110 0.7405 0.2212 0.042 Uiso 1 1 calc R . . H9B H 1.6324 0.9889 0.1794 0.042 Uiso 1 1 calc R . . H9C H 1.6890 0.7314 0.1387 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01575(16) 0.03653(19) 0.03300(19) -0.00426(15) 0.00680(12) -0.00146(14) O1 0.0152(10) 0.0237(11) 0.0197(10) -0.0023(8) 0.0031(8) -0.0049(8) O2 0.0161(10) 0.0344(12) 0.0175(11) -0.0086(9) 0.0017(8) -0.0040(9) O3 0.0206(10) 0.0169(10) 0.0231(10) 0.0036(9) -0.0079(8) -0.0039(8) O4 0.0343(13) 0.0367(13) 0.0222(12) 0.0117(10) -0.0015(10) -0.0018(10) C1 0.0195(15) 0.0181(13) 0.0136(14) 0.0029(11) 0.0014(11) 0.0000(11) C2 0.0186(15) 0.0211(15) 0.0183(15) 0.0034(12) -0.0029(12) -0.0011(12) C7 0.0182(13) 0.0203(14) 0.0135(13) 0.0044(12) 0.0021(10) -0.0033(12) C4 0.0279(17) 0.0247(16) 0.0226(17) -0.0030(13) 0.0057(13) 0.0028(13) C3 0.0303(17) 0.0198(15) 0.0213(16) -0.0040(12) -0.0031(13) 0.0037(12) C5 0.0162(14) 0.0243(15) 0.0210(16) 0.0011(12) 0.0028(12) -0.0018(12) C6 0.0170(13) 0.0187(14) 0.0177(14) -0.0022(12) 0.0030(11) -0.0014(12) C8 0.0248(16) 0.0204(14) 0.0158(15) -0.0056(12) -0.0028(12) 0.0024(12) C9 0.0255(16) 0.0262(16) 0.0296(17) -0.0004(14) -0.0079(13) -0.0027(13) _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 C5 1.896(3) . ? O1 C7 1.309(3) . ? O1 H1 0.8400 . ? O2 C7 1.228(3) . ? O3 C8 1.366(3) . ? O3 C2 1.401(3) . ? O4 C8 1.201(4) . ? C1 C2 1.401(4) . ? C1 C6 1.394(4) . ? C1 C7 1.492(4) . ? C2 C3 1.382(4) . ? C4 C5 1.383(4) . ? C4 C3 1.385(4) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C5 C6 1.385(4) . ? C6 H6 0.9500 . ? C8 C9 1.490(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.5 . . ? C8 O3 C2 117.8(2) . . ? C2 C1 C6 117.8(3) . . ? C2 C1 C7 125.7(3) . . ? C6 C1 C7 116.5(2) . . ? C1 C2 C3 121.4(3) . . ? C1 C2 O3 120.8(2) . . ? C3 C2 O3 117.6(3) . . ? O2 C7 O1 123.8(2) . . ? O2 C7 C1 120.1(2) . . ? O1 C7 C1 116.1(2) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 Br1 120.4(2) . . ? C6 C5 Br1 118.6(2) . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O4 C8 O3 122.2(3) . . ? O4 C8 C9 127.5(3) . . ? O3 C8 C9 110.2(2) . . ? 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 . . ? 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 1.79 2.625(3) 179.6 3_855 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.438 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.090 data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 643152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-chlorobenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-chlorobenzoic acid'" _chemical_melting_point 147 _chemical_formula_moiety 'C9 H7 Cl O4' _chemical_formula_sum 'C9 H7 Cl O4' _chemical_formula_weight 214.60 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' 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 _symmetry_space_group_name_Hall -P2yn 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 10.1217(4) _cell_length_b 4.73590(10) _cell_length_c 19.4447(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.219(2) _cell_angle_gamma 90.00 _cell_volume 926.60(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7186 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7954 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _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 95mm 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 12125 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2111 _reflns_number_gt 1608 _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^)+(0.0422P)^2^+0.3205P] 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 2111 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cl1 Cl 0.89012(4) 0.24922(10) 0.08962(3) 0.03417(16) Uani 1 1 d . . . O1 O 1.50405(11) 0.2919(2) 0.06227(6) 0.0240(3) Uani 1 1 d . . . H1 H 1.5531 0.1840 0.0420 0.036 Uiso 1 1 calc R . . O2 O 1.34381(12) 0.0617(3) -0.00313(6) 0.0276(3) Uani 1 1 d . . . O3 O 1.42747(12) 0.7354(2) 0.13518(6) 0.0243(3) Uani 1 1 d . . . O4 O 1.50466(13) 0.4410(3) 0.22098(6) 0.0363(3) Uani 1 1 d . . . C1 C 1.27844(17) 0.3778(3) 0.08062(8) 0.0208(4) Uani 1 1 d . . . C2 C 1.30452(17) 0.5978(3) 0.12809(8) 0.0225(4) Uani 1 1 d . . . C7 C 1.37923(17) 0.2334(3) 0.04250(8) 0.0209(4) Uani 1 1 d . . . C4 C 1.07763(19) 0.5956(4) 0.15396(9) 0.0288(4) Uani 1 1 d . . . H4 H 1.0097 0.6659 0.1794 0.035 Uiso 1 1 calc R . . C3 C 1.20569(19) 0.7033(4) 0.16482(9) 0.0276(4) Uani 1 1 d . . . H3 H 1.2256 0.8501 0.1976 0.033 Uiso 1 1 calc R . . C5 C 1.05048(17) 0.3837(4) 0.10529(9) 0.0248(4) Uani 1 1 d . . . C6 C 1.14872(18) 0.2738(3) 0.06894(9) 0.0230(4) Uani 1 1 d . . . H6 H 1.1281 0.1278 0.0360 0.028 Uiso 1 1 calc R . . C8 C 1.52437(18) 0.6337(4) 0.18347(9) 0.0247(4) Uani 1 1 d . . . C9 C 1.65038(19) 0.7914(4) 0.18035(10) 0.0317(4) Uani 1 1 d . . . H9A H 1.7132 0.7420 0.2205 0.047 Uiso 1 1 calc R . . H9B H 1.6325 0.9947 0.1807 0.047 Uiso 1 1 calc R . . H9C H 1.6887 0.7415 0.1378 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0198(3) 0.0406(3) 0.0428(3) -0.0079(2) 0.00690(19) -0.00353(19) O1 0.0178(6) 0.0295(7) 0.0247(7) -0.0023(5) 0.0031(5) -0.0044(5) O2 0.0225(7) 0.0365(7) 0.0236(6) -0.0077(5) 0.0021(5) -0.0044(5) O3 0.0241(7) 0.0196(6) 0.0274(7) 0.0018(5) -0.0055(5) -0.0030(5) O4 0.0364(8) 0.0424(8) 0.0289(7) 0.0113(6) -0.0011(6) -0.0014(6) C1 0.0224(9) 0.0209(8) 0.0189(8) 0.0032(7) 0.0010(6) -0.0016(7) C2 0.0228(9) 0.0204(9) 0.0230(9) 0.0033(7) -0.0033(7) -0.0032(7) C7 0.0209(9) 0.0239(9) 0.0176(8) 0.0036(7) 0.0006(7) -0.0042(7) C4 0.0302(10) 0.0291(10) 0.0276(10) -0.0022(7) 0.0053(8) 0.0040(8) C3 0.0314(11) 0.0223(9) 0.0282(10) -0.0042(7) -0.0008(8) 0.0018(8) C5 0.0199(9) 0.0277(9) 0.0267(9) -0.0001(7) 0.0024(7) -0.0016(7) C6 0.0241(9) 0.0237(9) 0.0213(9) -0.0027(7) 0.0029(7) -0.0031(7) C8 0.0294(10) 0.0230(9) 0.0207(9) -0.0030(7) -0.0024(7) 0.0033(7) C9 0.0291(10) 0.0288(10) 0.0344(11) 0.0009(8) -0.0089(8) -0.0023(8) _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 Cl1 C5 1.7394(17) . ? O1 C7 1.3097(19) . ? O1 H1 0.8400 . ? O2 C7 1.2281(19) . ? O3 C8 1.370(2) . ? O3 C2 1.398(2) . ? O4 C8 1.198(2) . ? C1 C6 1.398(2) . ? C1 C2 1.398(2) . ? C1 C7 1.490(2) . ? C2 C3 1.384(3) . ? C4 C5 1.386(2) . ? C4 C3 1.388(3) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C5 C6 1.383(2) . ? C6 H6 0.9500 . ? C8 C9 1.485(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.5 . . ? C8 O3 C2 117.85(13) . . ? C6 C1 C2 118.47(16) . . ? C6 C1 C7 116.05(15) . . ? C2 C1 C7 125.44(15) . . ? C3 C2 C1 120.97(16) . . ? C3 C2 O3 117.76(15) . . ? C1 C2 O3 121.00(15) . . ? O2 C7 O1 123.29(16) . . ? O2 C7 C1 120.07(15) . . ? O1 C7 C1 116.59(14) . . ? C5 C4 C3 118.88(17) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C2 C3 C4 120.26(16) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C6 C5 C4 121.40(16) . . ? C6 C5 Cl1 118.81(13) . . ? C4 C5 Cl1 119.79(14) . . ? C5 C6 C1 119.96(16) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O4 C8 O3 122.07(17) . . ? O4 C8 C9 127.46(16) . . ? O3 C8 C9 110.46(15) . . ? 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 . . ? 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 1.78 2.6233(17) 176.3 3_855 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.223 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.055 data_shelxl4 _database_code_depnum_ccdc_archive 'CCDC 643153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-fluorobenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-fluorobenzoic acid'" _chemical_melting_point 131 _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)/n _symmetry_space_group_name_Hall -P2yn 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 9.7655(5) _cell_length_b 4.8919(2) _cell_length_c 18.3338(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.739(3) _cell_angle_gamma 90.00 _cell_volume 847.02(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5271 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9537 _exptl_absorpt_correction_T_max 0.9973 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; 'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.715428' ; _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 95mm 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 7983 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1933 _reflns_number_gt 1371 _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 ? _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^)+(0.0622P)^2^+0.3309P] 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 1933 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 H1 H 0.406(3) 1.093(6) 0.4540(19) 0.073(9) Uiso 1 1 d . . . C1 C 0.48881(18) 0.7282(4) 0.32746(10) 0.0187(4) Uani 1 1 d . . . C2 C 0.57180(19) 0.5081(4) 0.31555(10) 0.0198(4) Uani 1 1 d . . . C3 C 0.5756(2) 0.4307(4) 0.24341(10) 0.0222(4) Uani 1 1 d . . . H3 H 0.6336 0.2819 0.2366 0.027 Uiso 1 1 calc R . . C4 C 0.4954(2) 0.5695(4) 0.18109(10) 0.0253(4) Uani 1 1 d . . . H4 H 0.4977 0.5184 0.1314 0.030 Uiso 1 1 calc R . . C5 C 0.4123(2) 0.7830(4) 0.19330(10) 0.0234(4) Uani 1 1 d . . . C6 C 0.40687(19) 0.8651(4) 0.26438(10) 0.0213(4) Uani 1 1 d . . . H6 H 0.3480 1.0134 0.2705 0.026 Uiso 1 1 calc R . . C7 C 0.49036(18) 0.8303(4) 0.40391(10) 0.0194(4) Uani 1 1 d . . . C8 C 0.77731(19) 0.4262(4) 0.41320(10) 0.0201(4) Uani 1 1 d . . . C9 C 0.8331(2) 0.2470(4) 0.47958(11) 0.0247(4) Uani 1 1 d . . . H9A H 0.9334 0.2884 0.5014 0.037 Uiso 1 1 calc R . . H9B H 0.8231 0.0552 0.4637 0.037 Uiso 1 1 calc R . . H9C H 0.7797 0.2793 0.5174 0.037 Uiso 1 1 calc R . . O1 O 0.39019(14) 1.0106(3) 0.40388(8) 0.0264(3) Uani 1 1 d . . . O2 O 0.57810(14) 0.7578(3) 0.46135(7) 0.0239(3) Uani 1 1 d . . . O3 O 0.64446(13) 0.3446(3) 0.37531(7) 0.0207(3) Uani 1 1 d . . . O4 O 0.83558(13) 0.6168(3) 0.39270(7) 0.0262(3) Uani 1 1 d . . . F F 0.33388(12) 0.9229(2) 0.13308(6) 0.0321(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 C1 0.0200(9) 0.0208(9) 0.0165(9) -0.0020(7) 0.0067(7) -0.0057(7) C2 0.0217(9) 0.0204(9) 0.0172(9) -0.0002(7) 0.0047(7) -0.0040(7) C3 0.0257(10) 0.0207(9) 0.0214(10) -0.0044(7) 0.0083(8) -0.0032(8) C4 0.0344(11) 0.0260(10) 0.0175(9) -0.0050(7) 0.0102(8) -0.0084(8) C5 0.0267(10) 0.0264(10) 0.0158(9) 0.0036(7) 0.0031(8) -0.0062(8) C6 0.0213(9) 0.0204(9) 0.0221(9) 0.0018(7) 0.0054(7) -0.0011(7) C7 0.0194(9) 0.0199(9) 0.0205(9) -0.0004(7) 0.0081(7) -0.0028(7) C8 0.0215(9) 0.0211(9) 0.0188(9) -0.0053(7) 0.0070(7) -0.0021(7) C9 0.0267(10) 0.0235(9) 0.0230(10) 0.0008(8) 0.0044(8) -0.0023(8) O1 0.0258(7) 0.0324(8) 0.0215(7) -0.0055(6) 0.0065(6) 0.0061(6) O2 0.0277(7) 0.0274(7) 0.0160(7) -0.0013(5) 0.0048(6) 0.0038(6) O3 0.0220(6) 0.0193(6) 0.0197(6) 0.0009(5) 0.0032(5) -0.0008(5) O4 0.0253(7) 0.0279(7) 0.0260(7) 0.0023(6) 0.0078(6) -0.0054(6) F 0.0383(7) 0.0346(7) 0.0196(6) 0.0073(5) 0.0003(5) -0.0020(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 C1 C2 1.398(3) . ? C1 C6 1.398(3) . ? C1 C7 1.484(2) . ? C2 C3 1.385(3) . ? C2 O3 1.396(2) . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 F 1.357(2) . ? C5 C6 1.377(3) . ? C6 H6 0.9500 . ? C7 O2 1.229(2) . ? C7 O1 1.317(2) . ? C8 O4 1.201(2) . ? C8 O3 1.366(2) . ? C8 C9 1.486(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 H1 0.98(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 118.18(16) . . ? C2 C1 C7 122.66(16) . . ? C6 C1 C7 119.08(16) . . ? C3 C2 O3 117.47(16) . . ? C3 C2 C1 121.14(16) . . ? O3 C2 C1 121.19(16) . . ? C2 C3 C4 120.38(18) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.07(17) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? F C5 C4 118.96(17) . . ? F C5 C6 118.25(17) . . ? C4 C5 C6 122.78(17) . . ? C5 C6 C1 119.43(17) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 O1 123.33(16) . . ? O2 C7 C1 123.34(16) . . ? O1 C7 C1 113.32(15) . . ? O4 C8 O3 122.12(17) . . ? O4 C8 C9 127.56(17) . . ? O3 C8 C9 110.32(15) . . ? 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 H1 109.7(18) . . ? C8 O3 C2 117.35(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.219 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.062 data_shelxl5 _database_code_depnum_ccdc_archive 'CCDC 643154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-iodobenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-iodobenzoic acid'" _chemical_melting_point 170 _chemical_formula_moiety 'C9 H7 I O4' _chemical_formula_sum 'C9 H7 I O4' _chemical_formula_weight 306.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 10.7838(5) _cell_length_b 4.7168(2) _cell_length_c 19.5502(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.630(2) _cell_angle_gamma 90.00 _cell_volume 987.77(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2344 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6981 _exptl_absorpt_correction_T_max 0.9094 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm 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 8826 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2238 _reflns_number_gt 1894 _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, 1997)' _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^)+(0.0000P)^2^+5.0845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2238 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 I1 I 0.90014(2) 0.23980(7) 0.091686(15) 0.02708(13) Uani 1 1 d . . . O1 O 1.5059(3) 0.2883(7) 0.06181(15) 0.0219(6) Uani 1 1 d . . . H1 H 1.5500 0.1828 0.0398 0.033 Uiso 1 1 calc R . . O2 O 1.3516(3) 0.0517(7) 0.00070(15) 0.0248(7) Uani 1 1 d . . . O3 O 1.4413(3) 0.7268(6) 0.13838(15) 0.0218(6) Uani 1 1 d . . . O4 O 1.5178(3) 0.4151(7) 0.21980(16) 0.0310(8) Uani 1 1 d . . . C1 C 1.2969(4) 0.3733(9) 0.0853(2) 0.0196(8) Uani 1 1 d . . . C2 C 1.3247(4) 0.5924(9) 0.1323(2) 0.0203(8) Uani 1 1 d . . . C7 C 1.3879(4) 0.2265(9) 0.0453(2) 0.0201(8) Uani 1 1 d . . . C4 C 1.1137(4) 0.6014(10) 0.1600(2) 0.0267(10) Uani 1 1 d . . . H4 H 1.0523 0.6755 0.1862 0.032 Uiso 1 1 calc R . . C3 C 1.2350(4) 0.7025(9) 0.1695(2) 0.0238(9) Uani 1 1 d . . . H3 H 1.2566 0.8493 0.2019 0.029 Uiso 1 1 calc R . . C5 C 1.0833(4) 0.3894(9) 0.1114(2) 0.0203(8) Uani 1 1 d . . . C6 C 1.1740(4) 0.2735(9) 0.0748(2) 0.0205(8) Uani 1 1 d . . . H6 H 1.1526 0.1259 0.0426 0.025 Uiso 1 1 calc R . . C8 C 1.5346(4) 0.6141(10) 0.1839(2) 0.0229(9) Uani 1 1 d . . . C9 C 1.6522(4) 0.7735(10) 0.1804(2) 0.0280(10) Uani 1 1 d . . . H9A H 1.7139 0.7157 0.2186 0.042 Uiso 1 1 calc R . . H9B H 1.6359 0.9771 0.1838 0.042 Uiso 1 1 calc R . . H9C H 1.6845 0.7331 0.1366 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01545(17) 0.0338(2) 0.03283(19) -0.00089(13) 0.00611(11) -0.00043(13) O1 0.0139(14) 0.0288(17) 0.0233(15) -0.0031(12) 0.0037(11) -0.0061(13) O2 0.0156(15) 0.0337(18) 0.0250(15) -0.0067(13) 0.0027(12) -0.0037(13) O3 0.0210(15) 0.0182(15) 0.0243(15) 0.0022(12) -0.0050(11) -0.0017(13) O4 0.0330(19) 0.0324(19) 0.0269(17) 0.0085(14) 0.0013(14) -0.0013(15) C1 0.018(2) 0.024(2) 0.0171(19) 0.0034(16) 0.0024(15) 0.0013(17) C2 0.016(2) 0.020(2) 0.025(2) 0.0032(16) 0.0003(16) -0.0023(16) C7 0.018(2) 0.024(2) 0.0181(18) 0.0059(17) 0.0022(15) -0.0028(18) C4 0.026(2) 0.029(2) 0.025(2) 0.0005(18) 0.0056(18) 0.005(2) C3 0.024(2) 0.021(2) 0.025(2) -0.0038(17) -0.0026(17) 0.0066(18) C5 0.015(2) 0.025(2) 0.021(2) 0.0042(16) 0.0032(15) 0.0008(17) C6 0.019(2) 0.021(2) 0.0212(19) 0.0002(16) 0.0036(15) -0.0017(17) C8 0.023(2) 0.022(2) 0.023(2) -0.0040(17) 0.0011(17) 0.0046(18) C9 0.024(2) 0.023(2) 0.034(2) -0.0001(19) -0.0070(18) -0.0015(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C5 2.091(4) . ? O1 C7 1.309(5) . ? O1 H1 0.8400 . ? O2 C7 1.231(5) . ? O3 C8 1.371(5) . ? O3 C2 1.401(5) . ? O4 C8 1.198(5) . ? C1 C2 1.392(6) . ? C1 C6 1.399(6) . ? C1 C7 1.493(6) . ? C2 C3 1.377(6) . ? C4 C3 1.384(6) . ? C4 C5 1.393(6) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C5 C6 1.389(6) . ? C6 H6 0.9500 . ? C8 C9 1.482(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.5 . . ? C8 O3 C2 117.6(3) . . ? C2 C1 C6 118.3(4) . . ? C2 C1 C7 125.8(4) . . ? C6 C1 C7 115.8(4) . . ? C3 C2 C1 121.1(4) . . ? C3 C2 O3 117.6(4) . . ? C1 C2 O3 121.0(4) . . ? O2 C7 O1 123.0(4) . . ? O2 C7 C1 120.5(4) . . ? O1 C7 C1 116.5(4) . . ? C3 C4 C5 118.9(4) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C6 C5 C4 120.6(4) . . ? C6 C5 I1 118.6(3) . . ? C4 C5 I1 120.8(3) . . ? C5 C6 C1 120.3(4) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O4 C8 O3 122.3(4) . . ? O4 C8 C9 127.8(4) . . ? O3 C8 C9 109.9(4) . . ? 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 . . ? 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 1.78 2.619(4) 175.7 3_855 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.559 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.125 data_shelxl6 _database_code_depnum_ccdc_archive 'CCDC 643155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-methylbenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-methylbenzoic acid'" _chemical_melting_point 146 _chemical_formula_moiety 'C10 H10 O4' _chemical_formula_sum 'C10 H10 O4' _chemical_formula_weight 194.18 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 _symmetry_space_group_name_Hall -P2yn 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 10.1301(3) _cell_length_b 4.88310(10) _cell_length_c 18.9682(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.696(2) _cell_angle_gamma 90.00 _cell_volume 921.98(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2304 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9425 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; 'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.794711' ; _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 95mm 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 10082 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2117 _reflns_number_gt 1616 _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 ? _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^)+(0.0574P)^2^+0.3231P] 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 2117 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 C10 C 0.35162(17) 0.8769(4) 0.14823(9) 0.0276(4) Uani 1 1 d . . . H10A H 0.3683 0.7938 0.1037 0.041 Uiso 0.50 1 calc PR . . H10B H 0.3754 1.0715 0.1490 0.041 Uiso 0.50 1 calc PR . . H10C H 0.2563 0.8578 0.1509 0.041 Uiso 0.50 1 calc PR . . H10D H 0.2984 1.0216 0.1654 0.041 Uiso 0.50 1 calc PR . . H10E H 0.2913 0.7439 0.1200 0.041 Uiso 0.50 1 calc PR . . H10F H 0.4104 0.9576 0.1182 0.041 Uiso 0.50 1 calc PR . . C1 C 0.50954(15) 0.6887(3) 0.34108(8) 0.0196(3) Uani 1 1 d . . . C2 C 0.59286(15) 0.4720(3) 0.32904(8) 0.0205(3) Uani 1 1 d . . . C3 C 0.60038(16) 0.3903(3) 0.26004(9) 0.0242(4) Uani 1 1 d . . . H3 H 0.6579 0.2439 0.2525 0.029 Uiso 1 1 calc R . . C4 C 0.52352(16) 0.5231(3) 0.20200(9) 0.0245(4) Uani 1 1 d . . . H4 H 0.5306 0.4691 0.1547 0.029 Uiso 1 1 calc R . . C5 C 0.43593(16) 0.7346(3) 0.21153(8) 0.0225(4) Uani 1 1 d . . . C6 C 0.43088(15) 0.8143(3) 0.28131(8) 0.0214(3) Uani 1 1 d . . . H6 H 0.3721 0.9588 0.2887 0.026 Uiso 1 1 calc R . . C7 C 0.50169(15) 0.8044(3) 0.41241(8) 0.0206(3) Uani 1 1 d . . . C8 C 0.78777(15) 0.3985(3) 0.41726(8) 0.0211(3) Uani 1 1 d . . . C9 C 0.84164(16) 0.2180(3) 0.47944(9) 0.0262(4) Uani 1 1 d . . . H9A H 0.9334 0.2745 0.5003 0.039 Uiso 1 1 calc R . . H9B H 0.8423 0.0276 0.4631 0.039 Uiso 1 1 calc R . . H9C H 0.7846 0.2332 0.5157 0.039 Uiso 1 1 calc R . . O2 O 0.41197(11) 0.9698(3) 0.41903(6) 0.0288(3) Uani 1 1 d . . . O1 O 0.59411(11) 0.7281(2) 0.46650(6) 0.0251(3) Uani 1 1 d . . . H1 H 0.5867 0.8200 0.5030 0.038 Uiso 1 1 calc R . . O3 O 0.66178(10) 0.3148(2) 0.38617(6) 0.0223(3) Uani 1 1 d . . . O4 O 0.84315(11) 0.5894(2) 0.39569(6) 0.0276(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 C10 0.0270(9) 0.0317(9) 0.0225(8) 0.0010(7) 0.0010(6) -0.0029(7) C1 0.0175(8) 0.0208(8) 0.0210(8) -0.0010(6) 0.0049(6) -0.0032(6) C2 0.0183(7) 0.0181(8) 0.0245(8) 0.0007(6) 0.0023(6) -0.0030(6) C3 0.0239(8) 0.0211(8) 0.0285(9) -0.0055(7) 0.0071(6) -0.0021(6) C4 0.0280(8) 0.0244(8) 0.0220(8) -0.0052(7) 0.0067(6) -0.0052(7) C5 0.0212(8) 0.0243(8) 0.0216(8) -0.0011(6) 0.0030(6) -0.0060(6) C6 0.0192(8) 0.0219(8) 0.0235(8) -0.0003(6) 0.0046(6) -0.0009(6) C7 0.0180(8) 0.0232(8) 0.0211(8) 0.0017(6) 0.0050(6) -0.0006(6) C8 0.0190(8) 0.0192(8) 0.0257(8) -0.0062(6) 0.0056(6) -0.0004(6) C9 0.0241(9) 0.0233(8) 0.0296(9) -0.0013(7) 0.0006(7) 0.0000(7) O2 0.0235(6) 0.0378(7) 0.0249(6) -0.0036(5) 0.0044(5) 0.0083(5) O1 0.0250(6) 0.0316(7) 0.0182(6) -0.0007(5) 0.0028(4) 0.0058(5) O3 0.0200(6) 0.0180(6) 0.0275(6) 0.0018(5) 0.0007(4) -0.0012(4) O4 0.0236(6) 0.0265(6) 0.0336(7) -0.0004(5) 0.0075(5) -0.0056(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 C10 C5 1.508(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10D 0.9800 . ? C10 H10E 0.9800 . ? C10 H10F 0.9800 . ? C1 C2 1.399(2) . ? C1 C6 1.400(2) . ? C1 C7 1.482(2) . ? C2 C3 1.384(2) . ? C2 O3 1.4037(19) . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.395(2) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C6 H6 0.9500 . ? C7 O2 1.2396(18) . ? C7 O1 1.3081(18) . ? C8 O4 1.1985(19) . ? C8 O3 1.3654(18) . ? C8 C9 1.492(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C10 H10D 109.5 . . ? H10A C10 H10D 141.1 . . ? H10B C10 H10D 56.3 . . ? H10C C10 H10D 56.3 . . ? C5 C10 H10E 109.5 . . ? H10A C10 H10E 56.3 . . ? H10B C10 H10E 141.1 . . ? H10C C10 H10E 56.3 . . ? H10D C10 H10E 109.5 . . ? C5 C10 H10F 109.5 . . ? H10A C10 H10F 56.3 . . ? H10B C10 H10F 56.3 . . ? H10C C10 H10F 141.1 . . ? H10D C10 H10F 109.5 . . ? H10E C10 H10F 109.5 . . ? C2 C1 C6 117.99(14) . . ? C2 C1 C7 125.01(14) . . ? C6 C1 C7 116.95(14) . . ? C3 C2 C1 120.89(15) . . ? C3 C2 O3 117.76(14) . . ? C1 C2 O3 121.10(13) . . ? C2 C3 C4 119.66(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 121.38(14) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 117.87(15) . . ? C6 C5 C10 120.91(15) . . ? C4 C5 C10 121.20(14) . . ? C5 C6 C1 122.16(15) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? O2 C7 O1 122.53(14) . . ? O2 C7 C1 120.36(14) . . ? O1 C7 C1 117.10(13) . . ? O4 C8 O3 123.00(15) . . ? O4 C8 C9 127.13(15) . . ? O3 C8 C9 109.87(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 . . ? C7 O1 H1 109.5 . . ? C8 O3 C2 117.44(12) . . ? 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 1.80 2.6354(16) 174.0 3_676 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.195 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.059 data_shelxl7 _database_code_depnum_ccdc_archive 'CCDC 643156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-acetyloxy-5-nitrobenzoic acid' ; _chemical_name_common "'2-acetyloxy-5-nitrobenzoic acid'" _chemical_melting_point 162 _chemical_formula_moiety 'C9 H7 N O6' _chemical_formula_sum 'C9 H7 N O6' _chemical_formula_weight 225.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn ' 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 9.9166(3) _cell_length_b 5.04440(10) _cell_length_c 18.6808(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.6860(10) _cell_angle_gamma 90.00 _cell_volume 921.15(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4600 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9333 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; 'SADABS results: Ratio of minimum to maximum apparent transmission: 0.836455' ; _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 95mm 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 8929 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2102 _reflns_number_gt 1804 _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 ? _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^)+(0.0496P)^2^+0.3793P] 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 2102 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O6 O 0.36435(10) 0.7492(2) 0.08354(5) 0.0214(2) Uani 1 1 d . . . O5 O 0.28836(11) 1.0388(2) 0.15267(5) 0.0289(3) Uani 1 1 d . . . N1 N 0.35863(11) 0.8454(2) 0.14331(6) 0.0165(2) Uani 1 1 d . . . C1 C 0.51004(12) 0.7049(2) 0.33681(6) 0.0138(3) Uani 1 1 d . . . C2 C 0.59018(12) 0.4836(2) 0.32678(6) 0.0143(3) Uani 1 1 d . . . C3 C 0.59775(13) 0.3878(3) 0.25788(7) 0.0171(3) Uani 1 1 d . . . H3 H 0.6548 0.2405 0.2524 0.020 Uiso 1 1 calc R . . C4 C 0.52233(13) 0.5064(3) 0.19712(7) 0.0164(3) Uani 1 1 d . . . H4 H 0.5265 0.4421 0.1498 0.020 Uiso 1 1 calc R . . C5 C 0.44076(12) 0.7210(3) 0.20732(6) 0.0142(3) Uani 1 1 d . . . C6 C 0.43315(12) 0.8228(3) 0.27534(6) 0.0146(3) Uani 1 1 d . . . H6 H 0.3764 0.9711 0.2802 0.017 Uiso 1 1 calc R . . C7 C 0.50266(12) 0.8242(3) 0.40944(6) 0.0144(3) Uani 1 1 d . . . C8 C 0.78697(12) 0.4084(3) 0.41542(7) 0.0153(3) Uani 1 1 d . . . C9 C 0.83853(14) 0.2353(3) 0.47864(7) 0.0185(3) Uani 1 1 d . . . H9A H 0.9341 0.2795 0.4975 0.028 Uiso 1 1 calc R . . H9B H 0.8322 0.0493 0.4633 0.028 Uiso 1 1 calc R . . H9C H 0.7832 0.2630 0.5168 0.028 Uiso 1 1 calc R . . O1 O 0.41227(9) 1.00710(19) 0.40919(5) 0.0206(2) Uani 1 1 d . . . H1 H 0.4212 1.0773 0.4505 0.031 Uiso 1 1 calc R . . O2 O 0.58303(10) 0.7491(2) 0.46457(5) 0.0228(2) Uani 1 1 d . . . O3 O 0.65588(9) 0.33661(18) 0.38549(5) 0.0162(2) Uani 1 1 d . . . O4 O 0.84551(10) 0.5850(2) 0.39047(5) 0.0247(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 O6 0.0257(5) 0.0256(5) 0.0125(4) -0.0032(4) 0.0019(4) 0.0001(4) O5 0.0322(6) 0.0326(6) 0.0213(5) -0.0002(4) 0.0031(4) 0.0186(5) N1 0.0151(5) 0.0195(5) 0.0148(5) -0.0016(4) 0.0020(4) 0.0011(4) C1 0.0132(6) 0.0152(6) 0.0137(6) -0.0020(4) 0.0039(4) -0.0036(5) C2 0.0137(6) 0.0134(6) 0.0155(6) 0.0013(4) 0.0014(4) -0.0033(5) C3 0.0179(6) 0.0141(6) 0.0196(6) -0.0016(5) 0.0044(5) 0.0022(5) C4 0.0185(6) 0.0163(6) 0.0149(6) -0.0032(5) 0.0044(5) -0.0006(5) C5 0.0130(6) 0.0162(6) 0.0131(6) -0.0005(4) 0.0016(4) -0.0013(5) C6 0.0138(6) 0.0147(6) 0.0158(6) -0.0017(5) 0.0040(5) -0.0002(5) C7 0.0138(6) 0.0157(6) 0.0140(6) -0.0005(5) 0.0037(4) -0.0035(5) C8 0.0151(6) 0.0154(6) 0.0157(6) -0.0011(5) 0.0036(5) -0.0005(5) C9 0.0198(6) 0.0182(6) 0.0170(6) 0.0029(5) 0.0013(5) -0.0024(5) O1 0.0210(5) 0.0231(5) 0.0188(5) -0.0074(4) 0.0062(4) 0.0008(4) O2 0.0251(5) 0.0298(6) 0.0127(4) -0.0015(4) 0.0006(4) 0.0008(4) O3 0.0152(5) 0.0149(4) 0.0176(4) 0.0034(3) 0.0002(3) -0.0023(3) O4 0.0200(5) 0.0257(5) 0.0275(5) 0.0109(4) 0.0015(4) -0.0070(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 O6 N1 1.2276(14) . ? O5 N1 1.2285(15) . ? N1 C5 1.4693(16) . ? C1 C6 1.3997(18) . ? C1 C2 1.4009(18) . ? C1 C7 1.4973(16) . ? C2 C3 1.3886(17) . ? C2 O3 1.3917(15) . ? C3 C4 1.3855(18) . ? C3 H3 0.9500 . ? C4 C5 1.3835(18) . ? C4 H4 0.9500 . ? C5 C6 1.3844(17) . ? C6 H6 0.9500 . ? C7 O2 1.2504(15) . ? C7 O1 1.2857(16) . ? C8 O4 1.1997(16) . ? C8 O3 1.3745(15) . ? C8 C9 1.4884(17) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 O6 N1 O5 123.88(11) . . ? O6 N1 C5 117.86(10) . . ? O5 N1 C5 118.26(10) . . ? C6 C1 C2 118.15(11) . . ? C6 C1 C7 118.01(11) . . ? C2 C1 C7 123.83(11) . . ? C3 C2 O3 116.99(11) . . ? C3 C2 C1 121.44(11) . . ? O3 C2 C1 121.34(11) . . ? C4 C3 C2 120.21(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 118.19(11) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 122.69(12) . . ? C4 C5 N1 118.62(11) . . ? C6 C5 N1 118.69(11) . . ? C5 C6 C1 119.28(12) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 124.61(11) . . ? O2 C7 C1 120.19(11) . . ? O1 C7 C1 115.18(11) . . ? O4 C8 O3 121.60(11) . . ? O4 C8 C9 128.31(12) . . ? O3 C8 C9 110.08(10) . . ? 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 H1 109.5 . . ? C8 O3 C2 117.75(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 2.6532(13) 171.8 3_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.293 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.055