# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Riccardo Montis' _publ_contact_author_email riccardo.montis@gmail.com loop_ _publ_author_name R.Montis M.Hursthouse data_3-methoxysalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871026' #TrackingRef '3-methoxysalicylic acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '3-methoxy-2-hydroxobenzoic acid ; _chemical_name_common '3-methoxysalicylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4' _chemical_formula_sum 'C8 H8 O4' _chemical_formula_weight 168.14 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/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 3.7935(2) _cell_length_b 27.8954(16) _cell_length_c 7.0172(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.891(3) _cell_angle_gamma 90.00 _cell_volume 739.86(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16762 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9854 _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 8164 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.55 _reflns_number_total 1678 _reflns_number_gt 1375 _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^)+(0.0588P)^2^+0.1938P] 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 1678 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.2884(4) 0.08657(5) 0.20592(19) 0.0200(3) Uani 1 1 d . . . C2 C 0.2968(4) 0.13426(5) 0.26801(19) 0.0201(3) Uani 1 1 d . . . C3 C 0.4106(4) 0.17040(5) 0.14574(19) 0.0198(3) Uani 1 1 d . . . C4 C 0.5136(4) 0.15791(5) -0.0323(2) 0.0230(3) Uani 1 1 d . . . H4 H 0.5914 0.1821 -0.1142 0.028 Uiso 1 1 calc R . . C5 C 0.5045(4) 0.11027(5) -0.0929(2) 0.0245(3) Uani 1 1 d . . . H5 H 0.5758 0.1023 -0.2155 0.029 Uiso 1 1 calc R . . C6 C 0.3933(4) 0.07475(5) 0.0237(2) 0.0236(3) Uani 1 1 d . . . H6 H 0.3871 0.0424 -0.0183 0.028 Uiso 1 1 calc R . . C7 C 0.1657(4) 0.04914(5) 0.33136(19) 0.0220(3) Uani 1 1 d . . . C8 C 0.5317(4) 0.25347(5) 0.1031(2) 0.0250(3) Uani 1 1 d . . . H8A H 0.7750 0.2465 0.0748 0.037 Uiso 1 1 calc R . . H8B H 0.5264 0.2839 0.1725 0.037 Uiso 1 1 calc R . . H8C H 0.3801 0.2558 -0.0168 0.037 Uiso 1 1 calc R . . O1 O 0.1811(3) 0.00494(4) 0.26644(15) 0.0306(3) Uani 1 1 d . . . O2 O 0.0538(3) 0.05803(4) 0.48978(14) 0.0264(3) Uani 1 1 d . . . O3 O 0.2016(3) 0.14869(4) 0.44092(14) 0.0257(3) Uani 1 1 d . . . O4 O 0.4054(3) 0.21574(3) 0.21838(14) 0.0243(3) Uani 1 1 d . . . H1A H 0.091(6) -0.0171(9) 0.356(3) 0.070(7) Uiso 1 1 d . . . H3A H 0.123(5) 0.1198(8) 0.493(3) 0.049(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0205(7) 0.0204(7) 0.0192(7) 0.0011(5) 0.0024(5) 0.0014(5) C2 0.0204(7) 0.0227(7) 0.0175(6) 0.0001(5) 0.0027(5) 0.0020(5) C3 0.0184(7) 0.0191(7) 0.0218(7) 0.0009(5) 0.0011(5) 0.0003(5) C4 0.0212(7) 0.0260(7) 0.0220(7) 0.0047(6) 0.0034(5) 0.0004(5) C5 0.0242(7) 0.0301(8) 0.0195(7) -0.0012(6) 0.0042(5) 0.0023(6) C6 0.0246(7) 0.0236(7) 0.0224(7) -0.0025(5) 0.0022(6) 0.0024(5) C7 0.0240(7) 0.0189(7) 0.0231(7) -0.0015(5) 0.0016(6) 0.0019(5) C8 0.0259(7) 0.0228(7) 0.0264(7) 0.0053(5) 0.0034(6) -0.0045(6) O1 0.0470(7) 0.0178(5) 0.0288(6) -0.0019(4) 0.0144(5) -0.0013(5) O2 0.0384(7) 0.0199(5) 0.0220(5) 0.0007(4) 0.0090(5) -0.0009(4) O3 0.0390(6) 0.0191(5) 0.0202(5) -0.0010(4) 0.0103(4) -0.0018(4) O4 0.0317(6) 0.0178(5) 0.0241(5) 0.0023(4) 0.0068(4) -0.0016(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 1.399(2) . ? C1 C6 1.4105(19) . ? C1 C7 1.4668(19) . ? C2 O3 1.3562(16) . ? C2 C3 1.4151(19) . ? C3 O4 1.3643(16) . ? C3 C4 1.3846(19) . ? C4 C5 1.395(2) . ? C4 H4 0.9500 . ? C5 C6 1.374(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.2482(16) . ? C7 O1 1.3175(16) . ? C8 O4 1.4345(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 H1A 0.96(3) . ? O3 H3A 0.94(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 C2 C1 C6 120.26(12) . . ? C2 C1 C7 119.33(12) . . ? C6 C1 C7 120.41(13) . . ? O3 C2 C1 124.06(12) . . ? O3 C2 C3 116.69(12) . . ? C1 C2 C3 119.25(12) . . ? O4 C3 C4 125.77(13) . . ? O4 C3 C2 114.77(12) . . ? C4 C3 C2 119.46(13) . . ? C3 C4 C5 120.89(13) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.43(13) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.73(13) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 121.50(12) . . ? O2 C7 C1 122.84(12) . . ? O1 C7 C1 115.66(12) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 O1 H1A 110.1(14) . . ? C2 O3 H3A 102.3(12) . . ? C3 O4 C8 116.95(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 H1A O2 0.96(3) 1.70(3) 2.6582(14) 177(2) 3_556 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.219 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.049 # Attachment '3-methoxysalicylic acid_monohydrate.cif' data_3-methoxysalicylic_acid_monohydrate _database_code_depnum_ccdc_archive 'CCDC 871027' #TrackingRef '3-methoxysalicylic acid_monohydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '3-methoxy-2-hydroxobenzoic acid monohydrate' ; _chemical_name_common '3-methoxysalicylic acid monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4, H2 O' _chemical_formula_sum 'C8 H10 O5' _chemical_formula_weight 186.16 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' 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 17.9971(3) _cell_length_b 14.3789(2) _cell_length_c 6.73370(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.1210(10) _cell_angle_gamma 90.00 _cell_volume 1742.20(5) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12542 _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 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9316 _exptl_absorpt_correction_T_max 0.9650 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25551 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3981 _reflns_number_gt 3481 _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_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^)+(0.0441P)^2^+0.6602P] 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 3981 _refine_ls_number_parameters 257 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 O31 O 0.80996(5) 0.94078(8) 0.84523(15) 0.0320(2) Uani 1 1 d D . . O41 O 1.31511(5) 0.55485(8) 1.37713(18) 0.0384(3) Uani 1 1 d D . . H31A H 0.8454(10) 0.9286(14) 0.770(3) 0.055(6) Uiso 1 1 d D . . H31B H 0.8275(10) 0.9745(13) 0.940(2) 0.056(6) Uiso 1 1 d D . . H41A H 1.3304(10) 0.5170(12) 1.465(3) 0.053(6) Uiso 1 1 d D . . H41B H 1.3484(10) 0.5959(12) 1.362(3) 0.062(6) Uiso 1 1 d D . . C11 C 0.57830(6) 0.77746(8) 0.83437(15) 0.0147(2) Uani 1 1 d . . . C12 C 0.50327(6) 0.80207(8) 0.83645(16) 0.0147(2) Uani 1 1 d . . . C13 C 0.44871(6) 0.73172(8) 0.83575(16) 0.0173(2) Uani 1 1 d . . . C14 C 0.46926(7) 0.63924(8) 0.83520(17) 0.0202(2) Uani 1 1 d . . . H14 H 0.4323 0.5921 0.8354 0.024 Uiso 1 1 calc R . . C15 C 0.54459(7) 0.61495(8) 0.83442(17) 0.0204(2) Uani 1 1 d . . . H15 H 0.5586 0.5512 0.8350 0.025 Uiso 1 1 calc R . . C16 C 0.59846(7) 0.68273(8) 0.83284(17) 0.0183(2) Uani 1 1 d . . . H16 H 0.6494 0.6657 0.8307 0.022 Uiso 1 1 calc R . . C17 C 0.63498(6) 0.85126(8) 0.83859(16) 0.0164(2) Uani 1 1 d . . . C18 C 0.31895(7) 0.69772(11) 0.8514(2) 0.0334(3) Uani 1 1 d . . . H18A H 0.3183 0.6579 0.7333 0.050 Uiso 1 1 calc R . . H18B H 0.2712 0.7299 0.8612 0.050 Uiso 1 1 calc R . . H18C H 0.3275 0.6595 0.9701 0.050 Uiso 1 1 calc R . . O11 O 0.70392(5) 0.82193(6) 0.83552(15) 0.0250(2) Uani 1 1 d . . . H11A H 0.7328 0.8678 0.8371 0.037 Uiso 1 1 calc R . . O12 O 0.61875(4) 0.93498(6) 0.84707(12) 0.01926(19) Uani 1 1 d . . . O13 O 0.47881(4) 0.89106(5) 0.84026(12) 0.01808(18) Uani 1 1 d . . . H13A H 0.5153 0.9273 0.8484 0.027 Uiso 1 1 calc R . . O14 O 0.37737(4) 0.76482(6) 0.83610(13) 0.0233(2) Uani 1 1 d . . . C21 C 1.08424(6) 0.60362(7) 1.03381(16) 0.0155(2) Uani 1 1 d . . . C22 C 1.00932(6) 0.60388(7) 1.08552(16) 0.0147(2) Uani 1 1 d . . . C23 C 0.95563(6) 0.63590(8) 0.94638(17) 0.0162(2) Uani 1 1 d . . . C24 C 0.97680(6) 0.66748(8) 0.76249(17) 0.0188(2) Uani 1 1 d . . . H24 H 0.9403 0.6894 0.6699 0.023 Uiso 1 1 calc R . . C25 C 1.05194(7) 0.66735(8) 0.71200(17) 0.0194(2) Uani 1 1 d . . . H25 H 1.0663 0.6892 0.5853 0.023 Uiso 1 1 calc R . . C26 C 1.10495(6) 0.63564(8) 0.84550(17) 0.0180(2) Uani 1 1 d . . . H26 H 1.1558 0.6354 0.8103 0.022 Uiso 1 1 calc R . . C27 C 1.14040(6) 0.57105(8) 1.18018(17) 0.0179(2) Uani 1 1 d . . . C28 C 0.82794(7) 0.67524(10) 0.8882(2) 0.0269(3) Uani 1 1 d . . . H28A H 0.7803 0.6742 0.9563 0.040 Uiso 1 1 calc R . . H28B H 0.8232 0.6411 0.7627 0.040 Uiso 1 1 calc R . . H28C H 0.8420 0.7398 0.8611 0.040 Uiso 1 1 calc R . . O21 O 1.20931(5) 0.57734(7) 1.12192(14) 0.0279(2) Uani 1 1 d . . . H21A H 1.2383 0.5620 1.2156 0.042 Uiso 1 1 calc R . . O22 O 1.12359(5) 0.54063(6) 1.34486(12) 0.0226(2) Uani 1 1 d . . . O23 O 0.98390(4) 0.57586(6) 1.26402(12) 0.01838(18) Uani 1 1 d . . . H23A H 1.0194 0.5551 1.3336 0.028 Uiso 1 1 calc R . . O24 O 0.88388(4) 0.63243(6) 1.01153(12) 0.02107(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O31 0.0230(5) 0.0433(6) 0.0300(5) -0.0163(4) 0.0089(4) -0.0137(4) O41 0.0221(5) 0.0389(6) 0.0536(7) 0.0255(5) -0.0157(4) -0.0105(4) C11 0.0169(5) 0.0156(5) 0.0115(5) -0.0005(4) -0.0014(4) 0.0007(4) C12 0.0186(5) 0.0151(5) 0.0104(5) 0.0003(4) -0.0003(4) 0.0005(4) C13 0.0168(5) 0.0211(6) 0.0139(5) -0.0007(4) 0.0004(4) -0.0015(4) C14 0.0267(6) 0.0180(6) 0.0158(5) -0.0011(4) 0.0002(4) -0.0067(5) C15 0.0298(6) 0.0148(5) 0.0166(5) -0.0007(4) -0.0021(5) 0.0006(5) C16 0.0220(6) 0.0176(6) 0.0150(5) -0.0011(4) -0.0021(4) 0.0032(4) C17 0.0166(5) 0.0185(5) 0.0142(5) -0.0003(4) -0.0011(4) 0.0016(4) C18 0.0210(6) 0.0360(8) 0.0433(8) -0.0050(6) 0.0051(6) -0.0136(5) O11 0.0142(4) 0.0203(4) 0.0404(5) -0.0017(4) -0.0013(4) 0.0004(3) O12 0.0183(4) 0.0149(4) 0.0246(4) -0.0006(3) -0.0012(3) -0.0003(3) O13 0.0161(4) 0.0149(4) 0.0232(4) 0.0001(3) -0.0002(3) 0.0013(3) O14 0.0143(4) 0.0250(5) 0.0308(5) -0.0016(4) 0.0026(3) -0.0046(3) C21 0.0162(5) 0.0129(5) 0.0174(5) -0.0007(4) -0.0004(4) -0.0012(4) C22 0.0174(5) 0.0117(5) 0.0151(5) -0.0006(4) 0.0013(4) -0.0007(4) C23 0.0156(5) 0.0135(5) 0.0196(5) -0.0007(4) 0.0005(4) 0.0012(4) C24 0.0216(6) 0.0164(5) 0.0185(6) 0.0029(4) -0.0022(4) 0.0024(4) C25 0.0245(6) 0.0168(5) 0.0169(5) 0.0024(4) 0.0033(4) -0.0008(4) C26 0.0174(5) 0.0157(5) 0.0209(6) -0.0006(4) 0.0034(4) -0.0017(4) C27 0.0159(5) 0.0172(5) 0.0206(6) -0.0003(4) 0.0003(4) -0.0015(4) C28 0.0176(6) 0.0327(7) 0.0302(7) 0.0065(5) -0.0039(5) 0.0082(5) O21 0.0133(4) 0.0427(6) 0.0276(5) 0.0106(4) -0.0009(3) -0.0020(4) O22 0.0182(4) 0.0304(5) 0.0191(4) 0.0053(3) -0.0006(3) 0.0023(3) O23 0.0157(4) 0.0241(4) 0.0154(4) 0.0046(3) 0.0013(3) 0.0010(3) O24 0.0136(4) 0.0275(5) 0.0221(4) 0.0059(3) -0.0004(3) 0.0045(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O31 H31A 0.841(14) . ? O31 H31B 0.856(14) . ? O41 H41A 0.848(14) . ? O41 H41B 0.848(14) . ? C11 C12 1.3962(15) . ? C11 C16 1.4097(15) . ? C11 C17 1.4718(15) . ? C12 O13 1.3535(13) . ? C12 C13 1.4098(16) . ? C13 O14 1.3692(14) . ? C13 C14 1.3804(17) . ? C14 C15 1.4000(17) . ? C14 H14 0.9500 . ? C15 C16 1.3749(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O12 1.2403(14) . ? C17 O11 1.3111(14) . ? C18 O14 1.4322(15) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O11 H11A 0.8400 . ? O13 H13A 0.8400 . ? C21 C22 1.3990(15) . ? C21 C26 1.4062(16) . ? C21 C27 1.4743(15) . ? C22 O23 1.3557(13) . ? C22 C23 1.4100(15) . ? C23 O24 1.3728(13) . ? C23 C24 1.3795(16) . ? C24 C25 1.4007(16) . ? C24 H24 0.9500 . ? C25 C26 1.3757(17) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O22 1.2352(14) . ? C27 O21 1.3113(14) . ? C28 O24 1.4317(14) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O21 H21A 0.8400 . ? O23 H23A 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 H31A O31 H31B 107.1(16) . . ? H41A O41 H41B 108.0(16) . . ? C12 C11 C16 119.62(10) . . ? C12 C11 C17 119.14(10) . . ? C16 C11 C17 121.22(10) . . ? O13 C12 C11 123.70(10) . . ? O13 C12 C13 116.84(10) . . ? C11 C12 C13 119.46(10) . . ? O14 C13 C14 125.89(10) . . ? O14 C13 C12 113.81(10) . . ? C14 C13 C12 120.30(11) . . ? C13 C14 C15 120.00(11) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.42(11) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 120.21(11) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O12 C17 O11 122.45(10) . . ? O12 C17 C11 122.48(10) . . ? O11 C17 C11 115.06(10) . . ? O14 C18 H18A 109.5 . . ? O14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 O11 H11A 109.5 . . ? C12 O13 H13A 109.5 . . ? C13 O14 C18 117.10(10) . . ? C22 C21 C26 119.82(10) . . ? C22 C21 C27 119.07(10) . . ? C26 C21 C27 121.10(10) . . ? O23 C22 C21 124.30(10) . . ? O23 C22 C23 116.58(10) . . ? C21 C22 C23 119.13(10) . . ? O24 C23 C24 125.23(10) . . ? O24 C23 C22 114.36(10) . . ? C24 C23 C22 120.41(10) . . ? C23 C24 C25 120.15(11) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 120.15(11) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 120.34(10) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? O22 C27 O21 122.88(11) . . ? O22 C27 C21 122.41(10) . . ? O21 C27 C21 114.72(10) . . ? O24 C28 H28A 109.5 . . ? O24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 O21 H21A 109.5 . . ? C22 O23 H23A 109.5 . . ? C23 O24 C28 117.01(9) . . ? 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 C16 C11 C12 O13 179.23(10) . . . . ? C17 C11 C12 O13 0.66(16) . . . . ? C16 C11 C12 C13 -0.39(16) . . . . ? C17 C11 C12 C13 -178.96(10) . . . . ? O13 C12 C13 O14 0.93(14) . . . . ? C11 C12 C13 O14 -179.43(9) . . . . ? O13 C12 C13 C14 -178.95(10) . . . . ? C11 C12 C13 C14 0.70(16) . . . . ? O14 C13 C14 C15 179.85(10) . . . . ? C12 C13 C14 C15 -0.29(17) . . . . ? C13 C14 C15 C16 -0.44(17) . . . . ? C14 C15 C16 C11 0.75(17) . . . . ? C12 C11 C16 C15 -0.33(17) . . . . ? C17 C11 C16 C15 178.20(10) . . . . ? C12 C11 C17 O12 1.15(16) . . . . ? C16 C11 C17 O12 -177.39(11) . . . . ? C12 C11 C17 O11 -179.76(10) . . . . ? C16 C11 C17 O11 1.70(15) . . . . ? C14 C13 O14 C18 4.69(17) . . . . ? C12 C13 O14 C18 -175.17(10) . . . . ? C26 C21 C22 O23 -178.93(10) . . . . ? C27 C21 C22 O23 0.02(16) . . . . ? C26 C21 C22 C23 0.41(16) . . . . ? C27 C21 C22 C23 179.36(10) . . . . ? O23 C22 C23 O24 -1.16(14) . . . . ? C21 C22 C23 O24 179.45(9) . . . . ? O23 C22 C23 C24 178.70(10) . . . . ? C21 C22 C23 C24 -0.69(16) . . . . ? O24 C23 C24 C25 -179.70(10) . . . . ? C22 C23 C24 C25 0.46(17) . . . . ? C23 C24 C25 C26 0.07(17) . . . . ? C24 C25 C26 C21 -0.35(17) . . . . ? C22 C21 C26 C25 0.11(17) . . . . ? C27 C21 C26 C25 -178.83(11) . . . . ? C22 C21 C27 O22 2.74(17) . . . . ? C26 C21 C27 O22 -178.32(11) . . . . ? C22 C21 C27 O21 -176.99(10) . . . . ? C26 C21 C27 O21 1.95(16) . . . . ? C24 C23 O24 C28 -7.91(16) . . . . ? C22 C23 O24 C28 171.94(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 O31 H31A O24 0.841(14) 2.079(15) 2.8363(13) 149.5(18) 4_575 O31 H31A O23 0.841(14) 2.495(17) 3.1973(12) 141.6(17) 4_575 O31 H31B O22 0.856(14) 1.932(15) 2.7837(12) 173.4(19) 2_757 O41 H41A O12 0.848(14) 1.944(15) 2.7838(13) 170.8(18) 2_747 O41 H41B O14 0.848(14) 2.078(16) 2.8404(14) 149.3(19) 4_676 O41 H41B O13 0.848(14) 2.362(18) 3.0618(13) 140.1(18) 4_676 O11 H11A O31 0.84 1.74 2.5616(12) 165.3 . O13 H13A O12 0.84 1.86 2.5961(11) 144.7 . O21 H21A O41 0.84 1.75 2.5603(13) 162.9 . O23 H23A O22 0.84 1.89 2.6114(11) 143.8 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.272 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.046 data_3-nitrosalicylic_acid_monohydrate _database_code_depnum_ccdc_archive 'CCDC 871028' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '3-nitro-2-hydroxybenzoic acid' ; _chemical_name_common "'3-nitro-2-hydroxybenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N O5, H2 O' _chemical_formula_sum 'C7 H7 N O6' _chemical_formula_weight 201.14 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)/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 3.5943(2) _cell_length_b 21.115(2) _cell_length_c 10.7227(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.950(6) _cell_angle_gamma 90.00 _cell_volume 803.87(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15824 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9708 _exptl_absorpt_correction_T_max 0.9911 _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 9655 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1833 _reflns_number_gt 1167 _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^)+(0.0490P)^2^+0.7958P] 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 1833 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1548 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.004 _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 O6 O 0.635(8) 0.5487(4) 0.0897(11) 0.035(4) Uani 0.35(4) 1 d P A 1 O6B O 0.405(7) 0.5506(3) 0.0773(5) 0.065(4) Uani 0.65(4) 1 d P A 2 C1 C 0.5457(8) 0.38901(13) 0.3784(3) 0.0240(6) Uani 1 1 d . . . C2 C 0.4491(7) 0.32472(13) 0.3564(3) 0.0228(6) Uani 1 1 d . . . C3 C 0.5617(7) 0.28213(13) 0.4546(3) 0.0239(6) Uani 1 1 d . . . C4 C 0.7461(7) 0.30153(14) 0.5712(3) 0.0266(7) Uani 1 1 d . . . H4 H 0.8163 0.2714 0.6363 0.032 Uiso 1 1 calc R . . C5 C 0.8285(8) 0.36547(14) 0.5928(3) 0.0284(7) Uani 1 1 d . . . H5 H 0.9500 0.3794 0.6732 0.034 Uiso 1 1 calc R . . C6 C 0.7316(8) 0.40815(14) 0.4962(3) 0.0281(7) Uani 1 1 d . . . H6 H 0.7928 0.4516 0.5101 0.034 Uiso 1 1 calc R . . C7 C 0.4491(8) 0.43462(14) 0.2745(3) 0.0294(7) Uani 1 1 d . . . N1 N 0.4903(7) 0.21426(11) 0.4380(2) 0.0276(6) Uani 1 1 d . . . O1 O 0.5890(6) 0.49216(9) 0.2983(2) 0.0374(6) Uani 1 1 d . . . H1 H 0.5350 0.5149 0.2338 0.056 Uiso 1 1 calc R . . O2 O 0.2602(6) 0.42026(9) 0.17307(19) 0.0348(6) Uani 1 1 d . . . O3 O 0.2641(6) 0.30512(9) 0.24563(18) 0.0286(5) Uani 1 1 d . . . H3 H 0.2232 0.3361 0.1963 0.043 Uiso 1 1 calc R . . O4 O 0.2523(6) 0.19604(10) 0.3510(2) 0.0410(6) Uani 1 1 d . . . O5 O 0.6731(6) 0.17754(10) 0.5130(2) 0.0375(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 O6 0.047(11) 0.027(4) 0.030(4) 0.000(3) 0.002(4) -0.001(4) O6B 0.113(13) 0.037(3) 0.041(3) 0.007(2) -0.002(4) -0.003(4) C1 0.0260(14) 0.0241(15) 0.0220(15) -0.0012(12) 0.0042(11) 0.0010(12) C2 0.0204(13) 0.0252(15) 0.0225(15) -0.0034(12) 0.0026(11) -0.0010(12) C3 0.0217(14) 0.0226(15) 0.0273(16) -0.0006(12) 0.0034(12) 0.0001(11) C4 0.0234(15) 0.0280(16) 0.0274(16) 0.0012(13) 0.0010(12) 0.0025(12) C5 0.0247(14) 0.0320(17) 0.0270(16) -0.0062(13) -0.0007(12) 0.0018(13) C6 0.0249(15) 0.0267(16) 0.0331(17) -0.0049(13) 0.0061(12) -0.0042(12) C7 0.0331(16) 0.0232(15) 0.0342(18) -0.0040(13) 0.0125(14) 0.0021(13) N1 0.0335(13) 0.0230(13) 0.0256(13) 0.0002(11) 0.0030(11) -0.0014(11) O1 0.0556(14) 0.0221(11) 0.0336(13) -0.0003(9) 0.0042(11) -0.0053(10) O2 0.0472(13) 0.0269(12) 0.0275(12) 0.0006(9) -0.0023(10) -0.0011(10) O3 0.0361(11) 0.0240(11) 0.0238(11) -0.0002(9) -0.0016(9) -0.0033(9) O4 0.0503(14) 0.0305(13) 0.0367(13) -0.0017(10) -0.0104(11) -0.0086(10) O5 0.0484(13) 0.0266(12) 0.0341(13) 0.0064(10) -0.0037(10) 0.0054(10) _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 C6 1.394(4) . ? C1 C2 1.412(4) . ? C1 C7 1.472(4) . ? C2 O3 1.333(3) . ? C2 C3 1.396(4) . ? C3 C4 1.383(4) . ? C3 N1 1.462(4) . ? C4 C5 1.394(4) . ? C4 H4 0.9500 . ? C5 C6 1.377(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.227(3) . ? C7 O1 1.324(3) . ? N1 O4 1.225(3) . ? N1 O5 1.231(3) . ? O1 H1 0.8400 . ? O3 H3 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 120.0(3) . . ? C6 C1 C7 121.3(3) . . ? C2 C1 C7 118.7(2) . . ? O3 C2 C3 121.2(3) . . ? O3 C2 C1 121.5(2) . . ? C3 C2 C1 117.3(2) . . ? C4 C3 C2 122.2(3) . . ? C4 C3 N1 116.8(3) . . ? C2 C3 N1 121.0(2) . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 121.5(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O2 C7 O1 122.6(3) . . ? O2 C7 C1 122.8(3) . . ? O1 C7 C1 114.6(3) . . ? O4 N1 O5 122.5(2) . . ? O4 N1 C3 119.3(2) . . ? O5 N1 C3 118.2(2) . . ? C7 O1 H1 109.5 . . ? C2 O3 H3 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 O6 0.84 1.79 2.563(9) 152.7 . O3 H3 O2 0.84 1.80 2.552(3) 147.8 . O1 H1 O6B 0.84 1.83 2.663(8) 169.4 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.266 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.069 data_4-acetamidosalacylic_acid _database_code_depnum_ccdc_archive 'CCDC 871029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-actyamino-2-hydroxobenzoic acid' ; _chemical_name_common "'4-actyamino-2-hydroxobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N O4' _chemical_formula_sum 'C9 H9 N O4' _chemical_formula_weight 195.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 13.5482(8) _cell_length_b 5.0245(3) _cell_length_c 12.9394(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 880.82(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6116 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9965 _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 5835 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1049 _reflns_number_gt 954 _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^)+(0.0601P)^2^+0.1048P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1049 _refine_ls_number_parameters 132 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.003 _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 O11 O 0.12497(12) -0.3421(3) 0.07559(14) 0.0261(4) Uani 1 1 d . . . O12 O 0.26959(12) -0.4858(3) 0.01301(13) 0.0239(4) Uani 1 1 d . . . H12 H 0.2325 -0.5914 -0.0189 0.036 Uiso 1 1 d R . . O15 O 0.32051(11) 0.6363(3) 0.40787(15) 0.0232(4) Uani 1 1 d . . . O13 O 0.12265(12) 0.0226(4) 0.21252(13) 0.0267(4) Uani 1 1 d . . . H13A H 0.1000 -0.0910 0.1712 0.040 Uiso 1 1 calc R . . N21 N 0.43438(14) 0.4008(4) 0.31610(16) 0.0193(4) Uani 1 1 d . . . C11 C 0.27270(16) -0.1388(5) 0.13482(16) 0.0172(4) Uani 1 1 d . . . C12 C 0.22231(16) 0.0325(5) 0.20356(18) 0.0186(5) Uani 1 1 d . . . C13 C 0.27289(16) 0.2148(5) 0.26455(16) 0.0182(5) Uani 1 1 d . . . H13 H 0.2381 0.3292 0.3103 0.022 Uiso 1 1 calc R . . C14 C 0.37525(16) 0.2272(5) 0.25747(16) 0.0171(5) Uani 1 1 d . . . C15 C 0.42639(16) 0.0592(5) 0.18900(18) 0.0207(5) Uani 1 1 d . . . H15 H 0.4962 0.0701 0.1840 0.025 Uiso 1 1 calc R . . C16 C 0.37552(16) -0.1205(5) 0.12941(17) 0.0200(5) Uani 1 1 d . . . H16 H 0.4108 -0.2341 0.0838 0.024 Uiso 1 1 calc R . . C17 C 0.21595(17) -0.3290(4) 0.07246(18) 0.0199(5) Uani 1 1 d . . . C18 C 0.40708(17) 0.5923(4) 0.38509(18) 0.0199(5) Uani 1 1 d . . . C20 C 0.49212(18) 0.7390(5) 0.4328(2) 0.0280(6) Uani 1 1 d . . . H20A H 0.4771 0.9297 0.4351 0.042 Uiso 1 1 calc R . . H20B H 0.5517 0.7100 0.3913 0.042 Uiso 1 1 calc R . . H20C H 0.5031 0.6732 0.5032 0.042 Uiso 1 1 calc R . . H21 H 0.500(3) 0.399(6) 0.301(3) 0.034 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 O11 0.0196(8) 0.0285(9) 0.0301(9) -0.0062(8) 0.0013(7) -0.0058(6) O12 0.0244(8) 0.0224(8) 0.0250(9) -0.0066(7) -0.0013(7) -0.0026(6) O15 0.0212(8) 0.0208(9) 0.0276(8) -0.0047(7) 0.0030(7) 0.0012(6) O13 0.0152(8) 0.0312(10) 0.0338(10) -0.0106(8) 0.0028(7) -0.0021(7) N21 0.0170(9) 0.0189(9) 0.0220(10) -0.0028(8) 0.0004(8) -0.0002(7) C11 0.0201(10) 0.0151(10) 0.0163(11) 0.0013(8) 0.0004(9) -0.0010(8) C12 0.0167(10) 0.0178(11) 0.0214(11) 0.0012(8) 0.0026(8) -0.0007(8) C13 0.0179(11) 0.0170(10) 0.0197(11) -0.0021(8) 0.0021(8) -0.0003(8) C14 0.0189(11) 0.0136(10) 0.0188(11) 0.0015(8) 0.0024(8) -0.0001(8) C15 0.0169(10) 0.0213(11) 0.0241(11) -0.0013(9) 0.0030(9) 0.0003(9) C16 0.0210(11) 0.0176(11) 0.0212(12) -0.0021(9) 0.0047(9) 0.0017(9) C17 0.0253(11) 0.0167(11) 0.0177(10) 0.0006(9) 0.0022(10) -0.0028(9) C18 0.0239(11) 0.0159(10) 0.0199(11) 0.0005(9) 0.0000(9) 0.0018(8) C20 0.0250(11) 0.0280(14) 0.0310(13) -0.0105(10) -0.0018(10) 0.0002(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C17 1.235(3) . ? O12 C17 1.319(3) . ? O12 H12 0.8397 . ? O15 C18 1.229(3) . ? O13 C12 1.356(3) . ? O13 H13A 0.8400 . ? N21 C18 1.363(3) . ? N21 C14 1.407(3) . ? N21 H21 0.90(3) . ? C11 C16 1.398(3) . ? C11 C12 1.413(3) . ? C11 C17 1.468(3) . ? C12 C13 1.390(3) . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 C15 1.406(3) . ? C15 C16 1.373(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C18 C20 1.501(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C17 O12 H12 109.5 . . ? C12 O13 H13A 109.5 . . ? C18 N21 C14 129.5(2) . . ? C18 N21 H21 114(2) . . ? C14 N21 H21 116(2) . . ? C16 C11 C12 118.21(19) . . ? C16 C11 C17 122.50(19) . . ? C12 C11 C17 119.29(19) . . ? O13 C12 C13 117.80(19) . . ? O13 C12 C11 120.82(19) . . ? C13 C12 C11 121.4(2) . . ? C12 C13 C14 118.9(2) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C13 C14 N21 124.0(2) . . ? C13 C14 C15 120.4(2) . . ? N21 C14 C15 115.56(19) . . ? C16 C15 C14 120.1(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.0(2) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O11 C17 O12 122.5(2) . . ? O11 C17 C11 122.6(2) . . ? O12 C17 C11 114.9(2) . . ? O15 C18 N21 122.9(2) . . ? O15 C18 C20 123.0(2) . . ? N21 C18 C20 114.1(2) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 O12 H12 O15 0.84 1.81 2.635(2) 166.3 3_534 N21 H21 O13 0.90(3) 2.06(3) 2.907(3) 155(3) 4 O13 H13A O11 0.84 1.80 2.549(2) 147.8 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.201 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.047 data_4-aminosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-amino-2-hydroxobenzoic acid' ; _chemical_name_common "'4-amino-2-hydroxobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3' _chemical_formula_sum 'C7 H7 N O3' _chemical_formula_weight 153.14 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 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 7.1371(3) _cell_length_b 3.7278(2) _cell_length_c 24.4465(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.386(2) _cell_angle_gamma 90.00 _cell_volume 648.51(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7209 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9975 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6128 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1475 _reflns_number_gt 1236 _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_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^)+(0.0462P)^2^+0.6212P] 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 1475 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 H1B H 0.569(3) 0.788(6) 0.2543(10) 0.033(6) Uiso 1 1 d . . . H1A H 0.735(3) 0.784(7) 0.2974(9) 0.036(6) Uiso 1 1 d . . . H1 H 0.155(4) 0.047(7) 0.5176(11) 0.043(7) Uiso 1 1 d . . . H3A H -0.037(4) 0.267(8) 0.3645(11) 0.051(8) Uiso 1 1 d . . . O2 O -0.01367(16) 0.1208(4) 0.43442(5) 0.0229(3) Uani 1 1 d . . . O1 O 0.23995(17) 0.1338(4) 0.49439(5) 0.0238(3) Uani 1 1 d . . . O3 O 0.01361(17) 0.3679(4) 0.33539(5) 0.0231(3) Uani 1 1 d . . . C1 C 0.2735(2) 0.3448(4) 0.40543(6) 0.0165(4) Uani 1 1 d . . . N1 N 0.6139(2) 0.7680(4) 0.28935(6) 0.0231(4) Uani 1 1 d . . . C5 C 0.5772(2) 0.5573(5) 0.38098(7) 0.0193(4) Uani 1 1 d . . . H5 H 0.7060 0.6054 0.3911 0.023 Uiso 1 1 calc R . . C2 C 0.1982(2) 0.4273(4) 0.35176(7) 0.0174(4) Uani 1 1 d . . . C3 C 0.3103(2) 0.5710(4) 0.31357(6) 0.0177(4) Uani 1 1 d . . . H3 H 0.2571 0.6282 0.2778 0.021 Uiso 1 1 calc R . . C7 C 0.1566(2) 0.1914(5) 0.44523(7) 0.0178(4) Uani 1 1 d . . . C6 C 0.4659(2) 0.4151(5) 0.41859(7) 0.0187(4) Uani 1 1 d . . . H6 H 0.5194 0.3623 0.4545 0.022 Uiso 1 1 calc R . . C4 C 0.5014(2) 0.6328(4) 0.32725(6) 0.0178(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 O2 0.0190(6) 0.0320(7) 0.0177(6) 0.0039(5) 0.0009(4) -0.0035(5) O1 0.0208(6) 0.0356(8) 0.0147(6) 0.0054(5) 0.0004(5) -0.0055(5) O3 0.0184(6) 0.0343(7) 0.0163(6) 0.0039(5) -0.0008(4) -0.0025(5) C1 0.0173(8) 0.0166(8) 0.0158(8) -0.0001(6) 0.0018(6) 0.0007(6) N1 0.0217(8) 0.0292(8) 0.0191(7) 0.0032(6) 0.0065(6) -0.0012(6) C5 0.0177(8) 0.0202(9) 0.0203(8) -0.0014(6) 0.0032(6) 0.0002(6) C2 0.0169(8) 0.0180(8) 0.0171(8) -0.0014(6) 0.0005(6) 0.0011(6) C3 0.0217(8) 0.0177(8) 0.0136(7) 0.0004(6) 0.0012(6) 0.0011(6) C7 0.0198(8) 0.0176(8) 0.0159(7) 0.0000(6) 0.0012(6) 0.0011(6) C6 0.0194(8) 0.0199(8) 0.0165(8) -0.0011(6) 0.0003(6) 0.0019(6) C4 0.0228(8) 0.0136(8) 0.0175(8) -0.0016(6) 0.0054(6) 0.0016(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 O2 C7 1.252(2) . ? O1 C7 1.3173(19) . ? O1 H1 0.92(3) . ? O3 C2 1.365(2) . ? O3 H3A 0.90(3) . ? C1 C6 1.410(2) . ? C1 C2 1.413(2) . ? C1 C7 1.447(2) . ? N1 C4 1.368(2) . ? N1 H1B 0.89(2) . ? N1 H1A 0.87(2) . ? C5 C6 1.368(2) . ? C5 C4 1.410(2) . ? C5 H5 0.9500 . ? C2 C3 1.383(2) . ? C3 C4 1.399(2) . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? 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 110.3(15) . . ? C2 O3 H3A 105.6(17) . . ? C6 C1 C2 117.76(15) . . ? C6 C1 C7 121.43(14) . . ? C2 C1 C7 120.81(15) . . ? C4 N1 H1B 119.5(15) . . ? C4 N1 H1A 119.7(15) . . ? H1B N1 H1A 119(2) . . ? C6 C5 C4 120.15(15) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? O3 C2 C3 117.39(14) . . ? O3 C2 C1 121.79(15) . . ? C3 C2 C1 120.82(15) . . ? C2 C3 C4 120.42(15) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O2 C7 O1 121.45(15) . . ? O2 C7 C1 122.80(15) . . ? O1 C7 C1 115.75(14) . . ? C5 C6 C1 121.63(15) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? N1 C4 C3 120.72(15) . . ? N1 C4 C5 120.09(15) . . ? C3 C4 C5 119.19(15) . . ? 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 179.91(15) . . . . ? C7 C1 C2 O3 0.3(3) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C7 C1 C2 C3 -179.43(15) . . . . ? O3 C2 C3 C4 -178.83(15) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C6 C1 C7 O2 -178.79(16) . . . . ? C2 C1 C7 O2 0.8(3) . . . . ? C6 C1 C7 O1 2.1(2) . . . . ? C2 C1 C7 O1 -178.29(15) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? C7 C1 C6 C5 179.46(16) . . . . ? C2 C3 C4 N1 178.67(16) . . . . ? C2 C3 C4 C5 -2.0(3) . . . . ? C6 C5 C4 N1 -178.63(16) . . . . ? C6 C5 C4 C3 2.0(3) . . . . ? 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 N1 H1A O3 0.87(2) 2.64(2) 3.338(2) 138(2) 1_655 O1 H1 O2 0.92(3) 1.72(3) 2.6394(17) 175(2) 3_556 O3 H3A O2 0.90(3) 1.79(3) 2.6114(17) 150(2) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.337 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.057 # Attachment '4-chlorosalicylic_acid.cif' data_4-chlorosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871031' #TrackingRef '4-chlorosalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-chloro-2-hydroxobenzoic acid' ; _chemical_name_common 4-chlorosalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Cl O3' _chemical_formula_sum 'C7 H5 Cl O3' _chemical_formula_weight 172.56 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 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 3.7241(2) _cell_length_b 14.4178(8) _cell_length_c 12.9156(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.933(3) _cell_angle_gamma 90.00 _cell_volume 686.84(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1518 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9287 _exptl_absorpt_correction_T_max 0.9950 _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 5857 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1556 _reflns_number_gt 1284 _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^)+(0.0000P)^2^+1.2925P] 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 1556 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.95831(18) 0.47559(4) 0.66680(5) 0.02622(19) Uani 1 1 d . . . O2 O 0.2151(5) 0.05295(13) 0.59915(14) 0.0272(4) Uani 1 1 d . . . O1 O 0.1402(5) 0.10606(13) 0.43516(14) 0.0270(4) Uani 1 1 d . . . H1 H 0.0295 0.0555 0.4244 0.040 Uiso 1 1 calc R . . O3 O 0.5507(6) 0.15543(14) 0.74935(15) 0.0325(5) Uani 1 1 d . . . H3 H 0.4428 0.1078 0.7239 0.049 Uiso 1 1 calc R . . C6 C 0.4722(7) 0.27212(17) 0.4932(2) 0.0203(5) Uani 1 1 d . . . H6 H 0.3839 0.2613 0.4216 0.024 Uiso 1 1 calc R . . C2 C 0.5723(7) 0.21831(17) 0.67232(19) 0.0209(5) Uani 1 1 d . . . C4 C 0.7622(7) 0.36970(17) 0.6279(2) 0.0210(5) Uani 1 1 d . . . C1 C 0.4369(7) 0.20264(17) 0.56687(19) 0.0190(5) Uani 1 1 d . . . C3 C 0.7363(7) 0.30280(18) 0.7030(2) 0.0232(6) Uani 1 1 d . . . H3A H 0.8285 0.3141 0.7742 0.028 Uiso 1 1 calc R . . C7 C 0.2575(7) 0.11460(17) 0.5354(2) 0.0210(5) Uani 1 1 d . . . C5 C 0.6332(7) 0.35605(18) 0.5227(2) 0.0223(5) Uani 1 1 d . . . H5 H 0.6553 0.4032 0.4725 0.027 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 0.0261(3) 0.0200(3) 0.0327(4) -0.0047(3) 0.0045(3) -0.0042(3) O2 0.0360(11) 0.0216(9) 0.0222(9) 0.0016(8) -0.0021(8) -0.0061(8) O1 0.0370(11) 0.0218(10) 0.0203(9) -0.0016(8) -0.0024(8) -0.0074(8) O3 0.0455(13) 0.0263(10) 0.0241(10) 0.0026(8) -0.0011(9) -0.0068(9) C6 0.0207(13) 0.0203(12) 0.0191(12) 0.0010(10) 0.0006(10) 0.0004(10) C2 0.0221(13) 0.0207(12) 0.0198(12) 0.0016(10) 0.0021(10) -0.0008(10) C4 0.0179(12) 0.0178(12) 0.0272(13) -0.0052(10) 0.0030(10) -0.0012(10) C1 0.0173(12) 0.0184(12) 0.0209(12) -0.0025(10) 0.0016(10) 0.0007(10) C3 0.0221(13) 0.0256(13) 0.0214(13) -0.0043(11) 0.0009(11) -0.0009(11) C7 0.0205(13) 0.0208(13) 0.0217(13) -0.0010(10) 0.0027(10) 0.0016(10) C5 0.0225(13) 0.0197(12) 0.0250(13) 0.0017(10) 0.0041(10) -0.0004(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 Cl1 C4 1.737(3) . ? O2 C7 1.236(3) . ? O1 C7 1.314(3) . ? O1 H1 0.8400 . ? O3 C2 1.357(3) . ? O3 H3 0.8400 . ? C6 C5 1.381(3) . ? C6 C1 1.400(3) . ? C6 H6 0.9500 . ? C2 C3 1.395(4) . ? C2 C1 1.404(3) . ? C4 C3 1.381(4) . ? C4 C5 1.391(4) . ? C1 C7 1.466(3) . ? C3 H3A 0.9500 . ? C5 H5 0.9500 . ? 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 . . ? C2 O3 H3 109.5 . . ? C5 C6 C1 121.1(2) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O3 C2 C3 116.3(2) . . ? O3 C2 C1 123.7(2) . . ? C3 C2 C1 120.0(2) . . ? C3 C4 C5 122.6(2) . . ? C3 C4 Cl1 118.6(2) . . ? C5 C4 Cl1 118.8(2) . . ? C6 C1 C2 119.3(2) . . ? C6 C1 C7 120.9(2) . . ? C2 C1 C7 119.8(2) . . ? C4 C3 C2 118.7(2) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? O2 C7 O1 122.2(2) . . ? O2 C7 C1 122.2(2) . . ? O1 C7 C1 115.5(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? 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 C5 C6 C1 C2 -0.9(4) . . . . ? C5 C6 C1 C7 178.4(2) . . . . ? O3 C2 C1 C6 179.9(2) . . . . ? C3 C2 C1 C6 0.7(4) . . . . ? O3 C2 C1 C7 0.6(4) . . . . ? C3 C2 C1 C7 -178.6(2) . . . . ? C5 C4 C3 C2 -0.4(4) . . . . ? Cl1 C4 C3 C2 178.7(2) . . . . ? O3 C2 C3 C4 -179.4(2) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C6 C1 C7 O2 -178.3(2) . . . . ? C2 C1 C7 O2 1.0(4) . . . . ? C6 C1 C7 O1 0.8(4) . . . . ? C2 C1 C7 O1 -179.9(2) . . . . ? C1 C6 C5 C4 0.4(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? Cl1 C4 C5 C6 -178.9(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 1.81 2.654(3) 179.3 3_556 O3 H3 O2 0.84 1.89 2.615(3) 144.2 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.360 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.075 data_4-methoxysalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-methoxy-2-hydroxobenzoic acid' ; _chemical_name_common "'4-methoxy-2-hydroxobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4' _chemical_formula_sum 'C8 H8 O4' _chemical_formula_weight 168.14 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 4.9629(2) _cell_length_b 11.0915(8) _cell_length_c 13.6559(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.788(4) _cell_angle_gamma 90.00 _cell_volume 742.88(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22874 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9562 _exptl_absorpt_correction_T_max 0.9855 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10375 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1704 _reflns_number_gt 1346 _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_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^)+(0.0655P)^2^+0.1762P] 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 1704 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 H3A H 0.542(4) 0.315(2) 0.5757(16) 0.043(6) Uiso 1 1 d . . . H8A H 1.276(4) 0.2872(17) 0.9288(13) 0.023(4) Uiso 1 1 d . . . H8B H 1.474(4) 0.3538(17) 0.8625(15) 0.030(5) Uiso 1 1 d . . . H8C H 1.514(4) 0.3790(19) 0.9772(15) 0.037(5) Uiso 1 1 d . . . C1 C 0.5560(3) 0.48996(14) 0.68054(11) 0.0207(3) Uani 1 1 d . . . C2 C 0.7305(3) 0.38918(14) 0.68545(11) 0.0208(3) Uani 1 1 d . . . C3 C 0.9511(3) 0.37823(14) 0.76213(11) 0.0219(4) Uani 1 1 d . . . H3 H 1.0669 0.3097 0.7657 0.026 Uiso 1 1 calc R . . C4 C 0.9988(3) 0.46879(14) 0.83308(11) 0.0219(4) Uani 1 1 d . . . C5 C 0.8289(3) 0.57048(14) 0.82876(12) 0.0236(4) Uani 1 1 d . . . H5 H 0.8642 0.6323 0.8772 0.028 Uiso 1 1 calc R . . C6 C 0.6110(3) 0.57967(14) 0.75379(11) 0.0229(4) Uani 1 1 d . . . H6 H 0.4950 0.6481 0.7514 0.027 Uiso 1 1 calc R . . C7 C 0.3224(3) 0.49829(14) 0.60185(11) 0.0215(4) Uani 1 1 d . . . C8 C 1.3793(3) 0.36197(15) 0.92068(13) 0.0271(4) Uani 1 1 d . . . O1 O 0.1762(2) 0.59768(10) 0.60045(8) 0.0267(3) Uani 1 1 d . . . H1 H 0.0440 0.5938 0.5541 0.040 Uiso 1 1 calc R . . O2 O 0.2628(2) 0.41677(10) 0.53920(8) 0.0252(3) Uani 1 1 d . . . O3 O 0.6944(2) 0.29850(10) 0.61834(8) 0.0273(3) Uani 1 1 d . . . O4 O 1.2047(2) 0.46564(10) 0.91071(8) 0.0258(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 0.0192(7) 0.0224(8) 0.0201(8) 0.0020(6) 0.0021(6) -0.0024(6) C2 0.0212(7) 0.0210(8) 0.0202(8) -0.0003(6) 0.0034(5) -0.0031(6) C3 0.0204(7) 0.0228(8) 0.0221(8) 0.0027(6) 0.0022(6) 0.0008(6) C4 0.0189(7) 0.0264(8) 0.0199(8) 0.0024(6) 0.0019(6) -0.0036(6) C5 0.0244(7) 0.0241(8) 0.0218(8) -0.0020(6) 0.0018(6) -0.0033(6) C6 0.0229(7) 0.0214(8) 0.0246(8) 0.0010(6) 0.0045(6) 0.0009(6) C7 0.0207(7) 0.0223(8) 0.0219(8) 0.0021(6) 0.0041(6) -0.0002(6) C8 0.0254(8) 0.0269(9) 0.0268(9) 0.0037(7) -0.0029(6) 0.0002(7) O1 0.0244(6) 0.0252(6) 0.0279(6) -0.0014(5) -0.0042(4) 0.0047(4) O2 0.0239(6) 0.0256(6) 0.0242(6) -0.0031(5) -0.0022(4) 0.0016(4) O3 0.0285(6) 0.0251(6) 0.0257(6) -0.0055(5) -0.0040(5) 0.0032(5) O4 0.0237(6) 0.0294(6) 0.0221(6) -0.0010(5) -0.0037(4) 0.0007(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 C6 1.408(2) . ? C1 C2 1.409(2) . ? C1 C7 1.458(2) . ? C2 O3 1.3540(19) . ? C2 C3 1.400(2) . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 O4 1.3558(17) . ? C4 C5 1.404(2) . ? C5 C6 1.375(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.2489(18) . ? C7 O1 1.3183(18) . ? C8 O4 1.434(2) . ? C8 H8A 0.989(19) . ? C8 H8B 0.99(2) . ? C8 H8C 0.96(2) . ? O1 H1 0.8400 . ? O3 H3A 0.90(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 C6 C1 C2 118.41(14) . . ? C6 C1 C7 121.66(14) . . ? C2 C1 C7 119.92(14) . . ? O3 C2 C3 116.70(14) . . ? O3 C2 C1 122.69(13) . . ? C3 C2 C1 120.60(14) . . ? C4 C3 C2 119.28(14) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? O4 C4 C3 123.64(14) . . ? O4 C4 C5 115.44(14) . . ? C3 C4 C5 120.91(14) . . ? C6 C5 C4 119.33(14) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 121.46(14) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O2 C7 O1 121.55(13) . . ? O2 C7 C1 122.51(14) . . ? O1 C7 C1 115.94(13) . . ? O4 C8 H8A 111.5(10) . . ? O4 C8 H8B 110.6(11) . . ? H8A C8 H8B 109.3(15) . . ? O4 C8 H8C 104.8(13) . . ? H8A C8 H8C 112.6(16) . . ? H8B C8 H8C 108.0(16) . . ? C7 O1 H1 109.5 . . ? C2 O3 H3A 107.1(14) . . ? C4 O4 C8 117.86(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 1.83 2.6720(14) 175.3 3_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.296 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.059 # Attachment '4-methylsalicylic_acid.cif' data_4-methylsalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871033' #TrackingRef '4-methylsalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-methyl-2-hydroxobenzoic acid' ; _chemical_name_common 4-methylsalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O3' _chemical_formula_sum 'C8 H8 O3' _chemical_formula_weight 152.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8685(3) _cell_length_b 7.2380(9) _cell_length_c 13.2142(15) _cell_angle_alpha 100.756(5) _cell_angle_beta 93.271(7) _cell_angle_gamma 90.788(7) _cell_volume 362.80(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10527 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_T_max 0.9968 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6688 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1630 _reflns_number_gt 1054 _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_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^)+(0.1061P)^2^+0.0210P] 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 1630 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1947 _refine_ls_wR_factor_gt 0.1704 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 C1 C 0.3797(5) 0.8518(3) 0.68183(15) 0.0451(5) Uani 1 1 d . . . C2 C 0.4639(5) 0.8202(3) 0.78154(17) 0.0490(6) Uani 1 1 d . . . C3 C 0.6229(5) 0.9644(3) 0.85514(17) 0.0526(6) Uani 1 1 d . . . C4 C 0.6947(5) 1.1379(3) 0.83184(17) 0.0492(6) Uani 1 1 d . . . C5 C 0.6114(6) 1.1688(3) 0.73240(18) 0.0543(6) Uani 1 1 d . . . C6 C 0.4547(6) 1.0276(3) 0.65879(17) 0.0525(6) Uani 1 1 d . . . C7 C 0.2127(5) 0.7016(3) 0.60382(16) 0.0489(6) Uani 1 1 d . . . C8 C 0.8593(6) 1.2937(3) 0.91280(19) 0.0625(7) Uani 1 1 d . . . H8A H 0.8070 1.2725 0.9815 0.094 Uiso 1 1 calc R . . H8B H 0.7672 1.4147 0.9024 0.094 Uiso 1 1 calc R . . H8C H 1.1108 1.2952 0.9071 0.094 Uiso 1 1 calc R . . O1 O 0.1524(5) 0.7431(2) 0.51217(12) 0.0692(6) Uani 1 1 d . . . O2 O 0.1343(4) 0.5457(2) 0.62209(13) 0.0651(5) Uani 1 1 d . . . O3 O 0.3977(5) 0.6552(2) 0.81184(14) 0.0736(6) Uani 1 1 d . . . H1A H 0.044(8) 0.644(5) 0.463(3) 0.103(10) Uiso 1 1 d . . . H3 H 0.654(7) 0.927(4) 0.924(2) 0.082(8) Uiso 1 1 d . . . H3A H 0.280(9) 0.573(5) 0.752(3) 0.121(12) Uiso 1 1 d . . . H5 H 0.644(6) 1.289(4) 0.7120(19) 0.067(7) Uiso 1 1 d . . . H6 H 0.398(6) 1.052(4) 0.589(2) 0.072(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0458(11) 0.0415(11) 0.0455(12) 0.0019(9) 0.0031(8) -0.0005(8) C2 0.0528(12) 0.0406(11) 0.0533(12) 0.0084(9) 0.0025(9) 0.0019(8) C3 0.0548(12) 0.0510(13) 0.0491(13) 0.0036(10) -0.0032(9) 0.0044(9) C4 0.0414(11) 0.0489(13) 0.0527(13) -0.0024(9) 0.0041(8) 0.0027(8) C5 0.0605(13) 0.0410(12) 0.0595(14) 0.0048(10) 0.0045(10) -0.0040(9) C6 0.0624(13) 0.0447(12) 0.0488(13) 0.0052(9) 0.0026(10) -0.0009(9) C7 0.0540(12) 0.0431(12) 0.0480(12) 0.0046(9) 0.0025(9) -0.0017(9) C8 0.0562(13) 0.0541(14) 0.0676(15) -0.0106(11) -0.0043(11) -0.0051(10) O1 0.1035(14) 0.0541(10) 0.0470(10) 0.0073(7) -0.0099(9) -0.0207(9) O2 0.0946(12) 0.0453(10) 0.0525(10) 0.0069(7) -0.0072(8) -0.0168(8) O3 0.1137(14) 0.0481(10) 0.0581(11) 0.0152(8) -0.0146(9) -0.0144(9) _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 1.393(3) . ? C1 C2 1.400(3) . ? C1 C7 1.466(3) . ? C2 O3 1.355(3) . ? C2 C3 1.396(3) . ? C3 C4 1.376(3) . ? C3 H3 1.00(3) . ? C4 C5 1.394(3) . ? C4 C8 1.508(3) . ? C5 C6 1.379(3) . ? C5 H5 0.96(3) . ? C6 H6 0.98(3) . ? C7 O2 1.234(2) . ? C7 O1 1.310(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 H1A 0.94(4) . ? O3 H3A 0.98(4) . ? 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 118.96(19) . . ? C6 C1 C7 121.03(19) . . ? C2 C1 C7 120.01(19) . . ? O3 C2 C3 117.1(2) . . ? O3 C2 C1 123.41(19) . . ? C3 C2 C1 119.5(2) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 127.1(16) . . ? C2 C3 H3 111.5(16) . . ? C3 C4 C5 119.2(2) . . ? C3 C4 C8 120.6(2) . . ? C5 C4 C8 120.2(2) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 116.2(15) . . ? C4 C5 H5 123.4(15) . . ? C5 C6 C1 120.9(2) . . ? C5 C6 H6 119.2(15) . . ? C1 C6 H6 119.9(15) . . ? O2 C7 O1 121.68(19) . . ? O2 C7 C1 122.87(19) . . ? O1 C7 C1 115.45(19) . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 O1 H1A 113.9(18) . . ? C2 O3 H3A 106(2) . . ? 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 179.15(18) . . . . ? C7 C1 C2 O3 -0.3(3) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? C7 C1 C2 C3 179.99(18) . . . . ? O3 C2 C3 C4 -178.88(18) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C2 C3 C4 C8 178.61(18) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C8 C4 C5 C6 -178.74(19) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C7 C1 C6 C5 179.89(19) . . . . ? C6 C1 C7 O2 -178.10(19) . . . . ? C2 C1 C7 O2 1.4(3) . . . . ? C6 C1 C7 O1 2.2(3) . . . . ? C2 C1 C7 O1 -178.30(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 0.94(4) 1.72(4) 2.660(2) 176(3) 2_566 O3 H3A O2 0.98(4) 1.75(4) 2.626(2) 147(3) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.202 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 data_5-acetamidosalicylic_acid_monohydrate _database_code_depnum_ccdc_archive 'CCDC 871034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-acetylamino-2-hydroxobenzoic acid monohydrate' ; _chemical_name_common "'5-acetylamino-2-hydroxobenzoic acid monohydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N O4, H2 O' _chemical_formula_sum 'C9 H11 N O5' _chemical_formula_weight 213.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.7472(4) _cell_length_b 11.5109(17) _cell_length_c 21.979(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 948.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8397 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9975 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4592 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1280 _reflns_number_gt 957 _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_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^+2.8855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1280 _refine_ls_number_parameters 151 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1151 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1573 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _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 H1B H 0.235(17) 0.417(5) 0.361(2) 0.018(15) Uiso 1 1 d . . . H5A H 0.710(18) 0.365(5) 0.0143(18) 0.04(2) Uiso 1 1 d D . . H5B H 0.59(2) 0.278(2) 0.053(3) 0.07(3) Uiso 1 1 d D . . C1 C 0.3184(16) 0.6010(5) 0.2109(3) 0.0232(13) Uani 1 1 d . . . C2 C 0.1581(16) 0.7107(4) 0.2182(2) 0.0217(13) Uani 1 1 d . . . C3 C 0.0618(17) 0.7481(5) 0.2758(3) 0.0249(13) Uani 1 1 d . . . H3 H -0.0411 0.8229 0.2808 0.030 Uiso 1 1 calc R . . C4 C 0.1130(16) 0.6782(4) 0.3260(3) 0.0245(13) Uani 1 1 d . . . H4 H 0.0413 0.7040 0.3652 0.029 Uiso 1 1 calc R . . C5 C 0.2714(16) 0.5693(4) 0.3187(3) 0.0207(12) Uani 1 1 d . . . C6 C 0.3732(17) 0.5315(4) 0.2623(3) 0.0227(13) Uani 1 1 d . . . H6 H 0.4821 0.4575 0.2580 0.027 Uiso 1 1 calc R . . C7 C 0.4181(17) 0.5603(5) 0.1494(2) 0.0239(13) Uani 1 1 d . . . C8 C 0.4511(17) 0.5158(5) 0.4230(3) 0.0281(14) Uani 1 1 d . . . C9 C 0.4884(19) 0.4155(5) 0.4669(3) 0.0334(16) Uani 1 1 d . . . H9A H 0.7417 0.4016 0.4752 0.050 Uiso 1 1 calc R . . H9B H 0.3824 0.3456 0.4490 0.050 Uiso 1 1 calc R . . H9C H 0.3651 0.4343 0.5050 0.050 Uiso 1 1 calc R . . N1 N 0.3117(14) 0.4912(4) 0.3688(2) 0.0252(12) Uani 1 1 d . . . O1 O 0.5545(14) 0.4560(3) 0.14855(18) 0.0320(11) Uani 1 1 d . . . H1 H 0.5665 0.4323 0.1125 0.048 Uiso 1 1 calc R . . O2 O 0.3737(13) 0.6207(3) 0.10372(18) 0.0325(11) Uani 1 1 d . . . O3 O 0.0965(13) 0.7816(3) 0.16911(19) 0.0317(11) Uani 1 1 d . . . H3A H 0.1750 0.7498 0.1374 0.047 Uiso 1 1 calc R . . O4 O 0.5456(13) 0.6144(3) 0.43868(18) 0.0306(10) Uani 1 1 d . . . O5 O 0.6093(17) 0.3512(4) 0.0480(2) 0.0417(13) Uani 1 1 d 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 0.025(3) 0.021(3) 0.023(3) 0.000(2) -0.003(3) -0.002(3) C2 0.026(3) 0.020(3) 0.020(3) 0.001(2) -0.003(3) -0.006(2) C3 0.023(3) 0.022(3) 0.030(3) -0.001(2) 0.000(3) -0.001(3) C4 0.025(3) 0.022(2) 0.027(3) -0.004(2) -0.001(3) -0.005(3) C5 0.021(3) 0.019(2) 0.023(3) 0.000(2) -0.001(2) -0.005(2) C6 0.027(3) 0.014(2) 0.027(3) -0.003(2) 0.002(3) -0.002(2) C7 0.027(3) 0.025(3) 0.019(3) 0.000(2) 0.003(3) -0.002(3) C8 0.023(3) 0.027(3) 0.034(3) 0.004(3) 0.004(3) 0.004(3) C9 0.039(4) 0.026(3) 0.035(3) 0.009(3) -0.002(3) 0.003(3) N1 0.031(3) 0.019(2) 0.026(3) 0.000(2) -0.003(2) -0.002(2) O1 0.048(3) 0.0240(19) 0.025(2) -0.0060(17) -0.002(2) 0.011(2) O2 0.045(3) 0.026(2) 0.026(2) 0.0021(17) 0.002(2) 0.002(2) O3 0.041(3) 0.0221(18) 0.032(2) 0.0004(17) -0.001(2) 0.010(2) O4 0.041(3) 0.0226(19) 0.028(2) -0.0040(17) -0.003(2) -0.002(2) O5 0.072(4) 0.027(2) 0.027(3) -0.0017(18) 0.010(3) -0.001(3) _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 C6 1.399(7) . ? C1 C2 1.408(7) . ? C1 C7 1.479(8) . ? C2 O3 1.373(6) . ? C2 C3 1.384(8) . ? C3 C4 1.380(8) . ? C3 H3 0.9500 . ? C4 C5 1.397(7) . ? C4 H4 0.9500 . ? C5 C6 1.368(7) . ? C5 N1 1.428(7) . ? C6 H6 0.9500 . ? C7 O2 1.232(6) . ? C7 O1 1.305(7) . ? C8 O4 1.239(7) . ? C8 N1 1.331(8) . ? C8 C9 1.511(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N1 H1B 0.91(6) . ? O1 H1 0.8400 . ? O3 H3A 0.8400 . ? O5 H5A 0.85(2) . ? O5 H5B 0.85(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 C6 C1 C2 118.8(5) . . ? C6 C1 C7 121.4(5) . . ? C2 C1 C7 119.7(5) . . ? O3 C2 C3 119.3(5) . . ? O3 C2 C1 121.0(5) . . ? C3 C2 C1 119.7(5) . . ? C4 C3 C2 120.9(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.5(5) . . ? C6 C5 N1 118.0(5) . . ? C4 C5 N1 121.4(5) . . ? C5 C6 C1 120.7(5) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 124.1(5) . . ? O2 C7 C1 122.2(5) . . ? O1 C7 C1 113.7(5) . . ? O4 C8 N1 123.8(5) . . ? O4 C8 C9 119.8(6) . . ? N1 C8 C9 116.4(5) . . ? 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 . . ? C8 N1 C5 126.6(5) . . ? C8 N1 H1B 119(3) . . ? C5 N1 H1B 115(4) . . ? C7 O1 H1 109.5 . . ? C2 O3 H3A 109.5 . . ? H5A O5 H5B 108(3) . . ? 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 O5 H5A O4 0.85(2) 1.91(2) 2.758(6) 176(6) 2_664 O5 H5B O4 0.85(2) 1.97(3) 2.802(6) 168(9) 3_645 O1 H1 O5 0.84 1.70 2.525(6) 165.5 . O3 H3A O2 0.84 1.82 2.564(6) 146.9 . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.343 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.084 # Attachment '5-aminosalicylic_acid.cif' data_5-aminosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871035' #TrackingRef '5-aminosalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-amino-2-hydroxobenzoic acid monohydrate' ; _chemical_name_common 5-aminosalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 N O3' _chemical_formula_sum 'C7 H7 N O3' _chemical_formula_weight 153.14 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 P21/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 3.7239(2) _cell_length_b 7.3696(4) _cell_length_c 23.3107(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.806(3) _cell_angle_gamma 90.00 _cell_volume 639.41(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4776 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9168 _exptl_absorpt_correction_T_max 0.9975 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5940 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1460 _reflns_number_gt 1077 _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_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^)+(0.0682P)^2^+0.1137P] 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 1460 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 H1B H -0.088(5) 0.191(3) 0.0288(8) 0.022(5) Uiso 1 1 d . . . H1A H 0.223(6) 0.085(3) 0.0443(9) 0.030(5) Uiso 1 1 d . . . H1C H -0.093(5) 0.063(3) 0.0835(8) 0.028(5) Uiso 1 1 d . . . H3A H 0.646(6) 0.795(3) 0.1816(10) 0.049(7) Uiso 1 1 d . . . C1 C 0.4114(4) 0.5996(2) 0.10969(7) 0.0131(4) Uani 1 1 d . . . C2 C 0.4527(4) 0.5679(2) 0.16886(7) 0.0145(4) Uani 1 1 d . . . C3 C 0.3500(4) 0.4009(2) 0.19177(7) 0.0183(4) Uani 1 1 d . . . H3 H 0.3735 0.3806 0.2320 0.022 Uiso 1 1 calc R . . C4 C 0.2152(4) 0.2659(2) 0.15642(7) 0.0161(4) Uani 1 1 d . . . H4 H 0.1450 0.1529 0.1721 0.019 Uiso 1 1 calc R . . C5 C 0.1823(4) 0.2957(2) 0.09784(7) 0.0145(4) Uani 1 1 d . . . C6 C 0.2755(4) 0.4602(2) 0.07428(7) 0.0128(4) Uani 1 1 d . . . H6 H 0.2475 0.4791 0.0341 0.015 Uiso 1 1 calc R . . C7 C 0.5091(4) 0.7781(2) 0.08393(7) 0.0146(4) Uani 1 1 d . . . N1 N 0.0426(4) 0.15014(19) 0.06028(7) 0.0160(4) Uani 1 1 d . . . O1 O 0.6545(3) 0.89630(15) 0.11729(5) 0.0205(3) Uani 1 1 d . . . O2 O 0.4443(3) 0.80733(15) 0.03151(5) 0.0192(3) Uani 1 1 d . . . O3 O 0.5854(3) 0.69506(16) 0.20563(5) 0.0213(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 0.0099(8) 0.0124(8) 0.0170(9) -0.0013(7) 0.0017(6) 0.0008(6) C2 0.0127(9) 0.0152(8) 0.0156(8) -0.0039(7) -0.0002(6) -0.0010(6) C3 0.0211(9) 0.0196(9) 0.0143(9) 0.0018(7) 0.0014(7) -0.0013(7) C4 0.0156(9) 0.0131(8) 0.0197(9) 0.0028(7) 0.0022(6) -0.0015(6) C5 0.0109(8) 0.0133(8) 0.0191(9) -0.0020(7) -0.0002(6) -0.0001(6) C6 0.0118(8) 0.0127(8) 0.0140(8) 0.0005(7) 0.0023(6) 0.0007(6) C7 0.0118(8) 0.0138(8) 0.0182(9) -0.0010(7) 0.0014(6) 0.0019(6) N1 0.0171(8) 0.0129(7) 0.0179(8) -0.0008(6) 0.0012(6) -0.0023(6) O1 0.0262(7) 0.0137(6) 0.0214(7) -0.0011(5) -0.0005(5) -0.0059(5) O2 0.0225(7) 0.0165(6) 0.0185(6) 0.0031(5) -0.0007(5) -0.0022(5) O3 0.0285(7) 0.0186(7) 0.0168(7) -0.0027(6) -0.0002(5) -0.0067(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 C6 1.402(2) . ? C1 C2 1.402(2) . ? C1 C7 1.496(2) . ? C2 O3 1.3530(19) . ? C2 C3 1.400(2) . ? C3 C4 1.377(2) . ? C3 H3 0.9500 . ? C4 C5 1.384(2) . ? C4 H4 0.9500 . ? C5 C6 1.380(2) . ? C5 N1 1.469(2) . ? C6 H6 0.9500 . ? C7 O2 1.257(2) . ? C7 O1 1.277(2) . ? N1 H1B 0.92(2) . ? N1 H1A 0.92(2) . ? N1 H1C 0.99(2) . ? O3 H3A 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 C6 C1 C2 118.91(14) . . ? C6 C1 C7 119.72(14) . . ? C2 C1 C7 121.37(14) . . ? O3 C2 C3 117.78(14) . . ? O3 C2 C1 122.30(14) . . ? C3 C2 C1 119.92(15) . . ? C4 C3 C2 120.40(15) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.68(15) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 121.07(15) . . ? C6 C5 N1 119.54(14) . . ? C4 C5 N1 119.38(14) . . ? C5 C6 C1 120.00(15) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O2 C7 O1 122.69(15) . . ? O2 C7 C1 119.96(14) . . ? O1 C7 C1 117.35(14) . . ? C5 N1 H1B 113.9(12) . . ? C5 N1 H1A 112.0(13) . . ? H1B N1 H1A 102.9(18) . . ? C5 N1 H1C 108.9(11) . . ? H1B N1 H1C 112.7(16) . . ? H1A N1 H1C 106.1(17) . . ? C2 O3 H3A 104.5(14) . . ? 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 N1 H1A O2 0.92(2) 2.23(2) 3.0223(19) 144.6(17) 1_545 N1 H1A O2 0.92(2) 2.33(2) 2.9301(19) 123.0(16) 3_665 O3 H3A O1 0.96(2) 1.68(2) 2.5572(17) 152(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.308 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.063 # Attachment '5-bromosalicylic_acid_alpha.cif' data_5-bromosalicylic_acid_alpha _database_code_depnum_ccdc_archive 'CCDC 871036' #TrackingRef '5-bromosalicylic_acid_alpha.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '5-bromosalicylic acid alpha' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Br O3' _chemical_formula_sum 'C7 H5 Br O3' _chemical_formula_weight 217.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.85140(10) _cell_length_b 11.6936(3) _cell_length_c 14.4341(3) _cell_angle_alpha 109.9910(10) _cell_angle_beta 98.066(2) _cell_angle_gamma 101.1680(10) _cell_volume 735.75(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8595 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 5.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1684 _exptl_absorpt_correction_T_max 0.6658 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10539 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3325 _reflns_number_gt 3072 _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 ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0111P)^2^+0.5756P] 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 3325 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0509 _refine_ls_wR_factor_gt 0.0490 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C11 C -0.4229(4) 0.67520(16) 0.45848(13) 0.0168(3) Uani 1 1 d . . . C12 C -0.4060(4) 0.66519(17) 0.35959(13) 0.0188(4) Uani 1 1 d . . . C13 C -0.1676(4) 0.73928(18) 0.34462(14) 0.0216(4) Uani 1 1 d . . . H15 H -0.1537 0.7319 0.2779 0.026 Uiso 1 1 calc R . . C14 C 0.0485(4) 0.82322(17) 0.42573(14) 0.0201(4) Uani 1 1 d . . . H14 H 0.2092 0.8739 0.4149 0.024 Uiso 1 1 calc R . . C15 C 0.0299(4) 0.83330(16) 0.52359(13) 0.0177(3) Uani 1 1 d . . . C16 C -0.2008(4) 0.76004(16) 0.54074(13) 0.0173(3) Uani 1 1 d . . . H12 H -0.2098 0.7668 0.6077 0.021 Uiso 1 1 calc R . . C17 C -0.6717(4) 0.59769(16) 0.47589(13) 0.0170(3) Uani 1 1 d . . . O11 O -0.6587(3) 0.61135(13) 0.57048(9) 0.0200(3) Uani 1 1 d . . . O12 O -0.8770(3) 0.52446(12) 0.40595(9) 0.0197(3) Uani 1 1 d . . . O13 O -0.6115(3) 0.58711(14) 0.27713(10) 0.0250(3) Uani 1 1 d . . . H11 H -0.797(6) 0.566(2) 0.5770(19) 0.036(7) Uiso 1 1 d . . . H13A H -0.735(5) 0.553(2) 0.2941(18) 0.030(7) Uiso 1 1 d . . . Br1 Br 0.32327(4) 0.951246(16) 0.635216(13) 0.02097(6) Uani 1 1 d . . . C21 C 1.0967(4) 0.71092(16) 1.01417(13) 0.0179(3) Uani 1 1 d . . . C22 C 1.1021(4) 0.79798(17) 1.11012(13) 0.0187(4) Uani 1 1 d . . . C23 C 0.9426(4) 0.88713(17) 1.11849(14) 0.0217(4) Uani 1 1 d . . . H23 H 0.9466 0.9466 1.1832 0.026 Uiso 1 1 calc R . . C24 C 0.7793(4) 0.88906(18) 1.03304(15) 0.0232(4) Uani 1 1 d . . . H24 H 0.6718 0.9500 1.0390 0.028 Uiso 1 1 calc R . . C25 C 0.7718(4) 0.80178(17) 0.93811(14) 0.0214(4) Uani 1 1 d . . . C26 C 0.9274(4) 0.71327(17) 0.92769(13) 0.0200(4) Uani 1 1 d . . . H26 H 0.9206 0.6541 0.8625 0.024 Uiso 1 1 calc R . . C27 C 1.2694(4) 0.61834(17) 1.00466(13) 0.0188(4) Uani 1 1 d . . . O21 O 1.2421(3) 0.53788(13) 0.91208(10) 0.0243(3) Uani 1 1 d . . . O22 O 1.4281(3) 0.61718(12) 1.07894(9) 0.0220(3) Uani 1 1 d . . . O23 O 1.2550(3) 0.80100(14) 1.19708(10) 0.0237(3) Uani 1 1 d . . . H21 H 1.348(6) 0.492(2) 0.9139(19) 0.036(7) Uiso 1 1 d . . . H23A H 1.331(6) 0.742(3) 1.181(2) 0.044(8) Uiso 1 1 d . . . Br2 Br 0.54749(4) 0.805772(19) 0.820961(14) 0.02859(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0165(8) 0.0169(8) 0.0195(8) 0.0083(7) 0.0060(7) 0.0063(7) C12 0.0186(8) 0.0199(9) 0.0194(9) 0.0087(7) 0.0038(7) 0.0063(7) C13 0.0240(9) 0.0254(9) 0.0216(9) 0.0134(8) 0.0093(7) 0.0091(8) C14 0.0185(8) 0.0207(9) 0.0252(9) 0.0121(7) 0.0078(7) 0.0058(7) C15 0.0162(8) 0.0155(8) 0.0214(9) 0.0067(7) 0.0036(7) 0.0052(7) C16 0.0187(8) 0.0174(8) 0.0172(8) 0.0071(7) 0.0050(7) 0.0064(7) C17 0.0188(8) 0.0162(8) 0.0188(8) 0.0079(7) 0.0055(7) 0.0080(7) O11 0.0174(6) 0.0231(7) 0.0193(6) 0.0105(5) 0.0044(5) 0.0004(5) O12 0.0188(6) 0.0200(6) 0.0186(6) 0.0075(5) 0.0031(5) 0.0015(5) O13 0.0213(7) 0.0316(8) 0.0168(7) 0.0085(6) 0.0027(6) -0.0022(6) Br1 0.01825(10) 0.01816(10) 0.02282(11) 0.00527(7) 0.00347(7) 0.00195(7) C21 0.0166(8) 0.0179(8) 0.0192(9) 0.0073(7) 0.0051(7) 0.0031(7) C22 0.0170(8) 0.0204(9) 0.0184(8) 0.0081(7) 0.0047(7) 0.0021(7) C23 0.0234(9) 0.0203(9) 0.0205(9) 0.0058(7) 0.0076(7) 0.0054(7) C24 0.0230(9) 0.0204(9) 0.0286(10) 0.0108(8) 0.0075(8) 0.0073(7) C25 0.0195(9) 0.0225(9) 0.0216(9) 0.0099(7) 0.0024(7) 0.0029(7) C26 0.0197(9) 0.0198(9) 0.0178(8) 0.0057(7) 0.0041(7) 0.0020(7) C27 0.0168(8) 0.0174(8) 0.0213(9) 0.0075(7) 0.0057(7) 0.0011(7) O21 0.0263(7) 0.0222(7) 0.0205(7) 0.0022(5) 0.0020(6) 0.0109(6) O22 0.0242(7) 0.0248(7) 0.0194(6) 0.0085(5) 0.0061(5) 0.0102(6) O23 0.0263(7) 0.0274(7) 0.0170(6) 0.0067(5) 0.0037(5) 0.0104(6) Br2 0.02928(12) 0.03374(12) 0.02439(11) 0.01413(9) 0.00117(8) 0.00966(9) _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 C11 C16 1.406(2) . ? C11 C12 1.407(2) . ? C11 C17 1.469(2) . ? C12 O13 1.347(2) . ? C12 C13 1.395(3) . ? C13 C14 1.380(3) . ? C13 H15 0.9500 . ? C14 C15 1.394(2) . ? C14 H14 0.9500 . ? C15 C16 1.378(2) . ? C15 Br1 1.8976(18) . ? C16 H12 0.9500 . ? C17 O12 1.241(2) . ? C17 O11 1.310(2) . ? O11 H11 0.81(3) . ? O13 H13A 0.77(3) . ? C21 C22 1.404(2) . ? C21 C26 1.406(2) . ? C21 C27 1.475(2) . ? C22 O23 1.351(2) . ? C22 C23 1.398(3) . ? C23 C24 1.379(3) . ? C23 H23 0.9500 . ? C24 C25 1.391(3) . ? C24 H24 0.9500 . ? C25 C26 1.376(3) . ? C25 Br2 1.8981(18) . ? C26 H26 0.9500 . ? C27 O22 1.235(2) . ? C27 O21 1.316(2) . ? O21 H21 0.82(3) . ? O23 H23A 0.83(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 C16 C11 C12 119.70(16) . . ? C16 C11 C17 120.06(15) . . ? C12 C11 C17 120.25(16) . . ? O13 C12 C13 117.48(16) . . ? O13 C12 C11 123.15(16) . . ? C13 C12 C11 119.37(16) . . ? C14 C13 C12 120.67(16) . . ? C14 C13 H15 119.7 . . ? C12 C13 H15 119.7 . . ? C13 C14 C15 119.73(17) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.98(16) . . ? C16 C15 Br1 119.35(13) . . ? C14 C15 Br1 119.66(13) . . ? C15 C16 C11 119.54(16) . . ? C15 C16 H12 120.2 . . ? C11 C16 H12 120.2 . . ? O12 C17 O11 122.84(16) . . ? O12 C17 C11 122.30(15) . . ? O11 C17 C11 114.86(15) . . ? C17 O11 H11 112.1(18) . . ? C12 O13 H13A 108.8(18) . . ? C22 C21 C26 119.59(16) . . ? C22 C21 C27 119.90(16) . . ? C26 C21 C27 120.51(16) . . ? O23 C22 C23 116.93(16) . . ? O23 C22 C21 123.43(16) . . ? C23 C22 C21 119.64(16) . . ? C24 C23 C22 120.19(17) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.06(17) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.94(17) . . ? C26 C25 Br2 119.37(14) . . ? C24 C25 Br2 119.69(14) . . ? C25 C26 C21 119.58(17) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? O22 C27 O21 122.77(17) . . ? O22 C27 C21 121.86(16) . . ? O21 C27 C21 115.37(16) . . ? C27 O21 H21 108.6(18) . . ? C22 O23 H23A 106.0(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 O11 H11 O12 0.81(3) 1.82(3) 2.6286(18) 175(3) 2_366 O21 H21 O22 0.82(3) 1.85(3) 2.6630(19) 176(3) 2_867 O23 H23A O22 0.83(3) 1.87(3) 2.6130(19) 149(3) . O13 H13A O12 0.77(3) 1.94(3) 2.6252(19) 147(2) . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.358 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.064 # Attachment '5-bromosalicylic_acid_beta.cif' data_5-bromosalicylic_acid_beta _database_code_depnum_ccdc_archive 'CCDC 871037' #TrackingRef '5-bromosalicylic_acid_beta.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '5-bromosalicylic acid beta' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Br O3' _chemical_formula_sum 'C7 H5 Br O3' _chemical_formula_weight 217.02 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9625(2) _cell_length_b 7.1714(3) _cell_length_c 8.0160(3) _cell_angle_alpha 82.112(2) _cell_angle_beta 73.835(2) _cell_angle_gamma 71.272(2) _cell_volume 363.56(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9241 _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 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.982 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 5.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4005 _exptl_absorpt_correction_T_max 0.9461 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7522 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0292 _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 -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.75 _reflns_number_total 1677 _reflns_number_gt 1564 _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 ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0000P)^2^+0.5187P] 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 1677 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 Br1 Br 0.15463(4) 0.15977(4) 0.86542(3) 0.02573(10) Uani 1 1 d . . . O11 O 0.3411(3) 0.4012(3) 0.1944(2) 0.0246(4) Uani 1 1 d . . . H11A H 0.3314 0.4672 0.0861 0.037 Uiso 1 1 d R . . O12 O 0.6740(3) 0.4068(3) 0.1104(2) 0.0228(4) Uani 1 1 d . . . O13 O 0.9130(3) 0.2729(3) 0.3280(2) 0.0261(4) Uani 1 1 d . . . H13A H 0.8808 0.3188 0.2372 0.039 Uiso 1 1 d R . . C11 C 0.5453(4) 0.2886(3) 0.3980(3) 0.0175(5) Uani 1 1 d . . . C12 C 0.7385(4) 0.2443(4) 0.4399(3) 0.0201(5) Uani 1 1 d . . . C13 C 0.7551(4) 0.1675(4) 0.6066(3) 0.0232(5) Uani 1 1 d . . . H13 H 0.8862 0.1340 0.6349 0.028 Uiso 1 1 calc R . . C14 C 0.5837(4) 0.1398(4) 0.7301(3) 0.0226(5) Uani 1 1 d . . . H14 H 0.5963 0.0868 0.8432 0.027 Uiso 1 1 calc R . . C15 C 0.3913(4) 0.1896(4) 0.6889(3) 0.0193(5) Uani 1 1 d . . . C16 C 0.3702(4) 0.2610(3) 0.5247(3) 0.0187(5) Uani 1 1 d . . . H16 H 0.2388 0.2912 0.4975 0.022 Uiso 1 1 calc R . . C17 C 0.5257(4) 0.3697(3) 0.2224(3) 0.0193(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02502(15) 0.03473(16) 0.01753(14) 0.00120(10) -0.00256(10) -0.01242(11) O11 0.0216(9) 0.0348(11) 0.0204(9) 0.0084(8) -0.0081(7) -0.0142(8) O12 0.0199(9) 0.0254(9) 0.0199(9) 0.0036(7) -0.0015(7) -0.0074(8) O13 0.0172(9) 0.0340(11) 0.0254(10) 0.0032(8) -0.0041(7) -0.0084(8) C11 0.0186(12) 0.0159(11) 0.0182(12) -0.0021(9) -0.0048(9) -0.0046(10) C12 0.0174(12) 0.0193(12) 0.0216(12) -0.0037(9) -0.0020(10) -0.0043(10) C13 0.0193(12) 0.0248(13) 0.0261(13) -0.0026(10) -0.0093(10) -0.0038(10) C14 0.0258(13) 0.0219(13) 0.0203(12) -0.0004(10) -0.0090(10) -0.0051(11) C15 0.0209(12) 0.0195(12) 0.0169(12) -0.0010(9) -0.0019(9) -0.0076(10) C16 0.0171(11) 0.0187(12) 0.0210(12) -0.0019(9) -0.0054(9) -0.0055(10) C17 0.0215(12) 0.0151(11) 0.0217(12) -0.0017(9) -0.0056(10) -0.0054(10) _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 Br1 C15 1.899(2) . ? O11 C17 1.309(3) . ? O11 H11A 0.9389 . ? O12 C17 1.240(3) . ? O13 C12 1.351(3) . ? O13 H13A 0.8160 . ? C11 C16 1.403(3) . ? C11 C12 1.404(3) . ? C11 C17 1.473(3) . ? C12 C13 1.395(4) . ? C13 C14 1.373(4) . ? C13 H13 0.9500 . ? C14 C15 1.392(3) . ? C14 H14 0.9500 . ? C15 C16 1.375(3) . ? C16 H16 0.9500 . ? 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 C17 O11 H11A 112.1 . . ? C12 O13 H13A 106.3 . . ? C16 C11 C12 120.0(2) . . ? C16 C11 C17 120.2(2) . . ? C12 C11 C17 119.8(2) . . ? O13 C12 C13 116.8(2) . . ? O13 C12 C11 124.0(2) . . ? C13 C12 C11 119.3(2) . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 121.3(2) . . ? C16 C15 Br1 120.01(19) . . ? C14 C15 Br1 118.70(19) . . ? C15 C16 C11 119.1(2) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? O12 C17 O11 122.8(2) . . ? O12 C17 C11 121.9(2) . . ? O11 C17 C11 115.3(2) . . ? 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 C16 C11 C12 O13 -177.6(2) . . . . ? C17 C11 C12 O13 0.5(4) . . . . ? C16 C11 C12 C13 1.9(4) . . . . ? C17 C11 C12 C13 -180.0(2) . . . . ? O13 C12 C13 C14 177.9(2) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 2.0(4) . . . . ? C13 C14 C15 Br1 -177.40(19) . . . . ? C14 C15 C16 C11 -1.6(4) . . . . ? Br1 C15 C16 C11 177.71(17) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C17 C11 C16 C15 -178.4(2) . . . . ? C16 C11 C17 O12 175.7(2) . . . . ? C12 C11 C17 O12 -2.4(4) . . . . ? C16 C11 C17 O11 -3.6(3) . . . . ? C12 C11 C17 O11 178.3(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 O11 H11A O12 0.94 1.71 2.646(2) 176.3 2_665 O13 H13A O12 0.82 1.89 2.620(2) 148.9 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.604 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.093 # Attachment '5-iodosalicylic acid_alpha.cif' data_5-iodosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871038' #TrackingRef '5-iodosalicylic acid_alpha.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-iodo-2-hydroxobenzoic acid' ; _chemical_name_common 5-iodosalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 I O3' _chemical_formula_sum 'C7 H5 I O3' _chemical_formula_weight 264.01 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 38.4671(15) _cell_length_b 4.5765(2) _cell_length_c 19.9300(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.789(2) _cell_angle_gamma 90.00 _cell_volume 3074.9(2) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3353 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 4.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4932 _exptl_absorpt_correction_T_max 0.6836 _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 11602 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3442 _reflns_number_gt 2638 _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^)+(0.0058P)^2^+25.5950P] 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 3442 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.011 _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 C11 C 0.41133(11) 0.3462(9) 0.8593(2) 0.0181(8) Uani 1 1 d . . . C12 C 0.41061(12) 0.1284(9) 0.9083(2) 0.0227(9) Uani 1 1 d . . . C13 C 0.37446(14) 0.0303(10) 0.8994(3) 0.0264(9) Uani 1 1 d . . . C14 C 0.33919(13) 0.1443(9) 0.8426(2) 0.0229(9) Uani 1 1 d . . . C15 C 0.33977(11) 0.3553(9) 0.7933(2) 0.0217(9) Uani 1 1 d . . . C16 C 0.37532(12) 0.4620(9) 0.8019(2) 0.0193(8) Uani 1 1 d . . . C17 C 0.44917(12) 0.4489(9) 0.8682(2) 0.0213(8) Uani 1 1 d . . . I11 I 0.286830(7) 0.51771(6) 0.703179(15) 0.02674(10) Uani 1 1 d . . . O11 O 0.44705(9) 0.6653(7) 0.82252(17) 0.0260(7) Uani 1 1 d . . . O12 O 0.48128(8) 0.3405(7) 0.91510(16) 0.0254(6) Uani 1 1 d . . . O13 O 0.44387(10) 0.0047(7) 0.96399(18) 0.0301(7) Uani 1 1 d . . . C21 C 0.41084(11) 0.2373(9) 1.1060(2) 0.0195(8) Uani 1 1 d . . . C22 C 0.40873(12) 0.0256(9) 1.1541(2) 0.0207(8) Uani 1 1 d . . . C23 C 0.37219(14) -0.0451(11) 1.1475(3) 0.0283(10) Uani 1 1 d . . . C24 C 0.33772(13) 0.0896(10) 1.0927(2) 0.0254(9) Uani 1 1 d . . . C25 C 0.34000(11) 0.2965(9) 1.0435(2) 0.0227(9) Uani 1 1 d . . . C26 C 0.37615(12) 0.3719(9) 1.0507(2) 0.0240(9) Uani 1 1 d . . . C27 C 0.44926(11) 0.3235(9) 1.1133(2) 0.0201(8) Uani 1 1 d . . . I21 I 0.288542(7) 0.49233(6) 0.957331(16) 0.02918(10) Uani 1 1 d . . . O21 O 0.44742(9) 0.5383(7) 1.06884(18) 0.0278(7) Uani 1 1 d . . . O22 O 0.48094(8) 0.2032(6) 1.15876(15) 0.0248(6) Uani 1 1 d . . . O23 O 0.44082(10) -0.1188(7) 1.20799(18) 0.0269(7) Uani 1 1 d . . . H11A H 0.4670(19) 0.712(14) 0.825(4) 0.07(2) Uiso 1 1 d . . . H13 H 0.3753(14) -0.100(11) 0.932(3) 0.028(13) Uiso 1 1 d . . . H13A H 0.4629(18) 0.080(13) 0.962(3) 0.053(19) Uiso 1 1 d . . . H14 H 0.3153(14) 0.080(10) 0.836(2) 0.021(11) Uiso 1 1 d . . . H16 H 0.3759(14) 0.619(11) 0.765(3) 0.032(13) Uiso 1 1 d . . . H21A H 0.4670(18) 0.584(13) 1.066(3) 0.055(19) Uiso 1 1 d . . . H23 H 0.3707(15) -0.186(11) 1.179(3) 0.038(14) Uiso 1 1 d . . . H23A H 0.4578(16) -0.072(12) 1.209(3) 0.028(16) Uiso 1 1 d . . . H24 H 0.3143(14) 0.031(9) 1.091(2) 0.022(12) Uiso 1 1 d . . . H26 H 0.3757(16) 0.524(11) 1.011(3) 0.044(16) 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 C11 0.0148(18) 0.0210(19) 0.0181(18) -0.0016(16) 0.0076(15) -0.0016(15) C12 0.022(2) 0.022(2) 0.0224(19) -0.0005(17) 0.0100(17) 0.0016(16) C13 0.027(2) 0.029(2) 0.026(2) 0.0053(19) 0.0149(19) 0.0045(18) C14 0.022(2) 0.023(2) 0.028(2) -0.0045(17) 0.0149(18) -0.0018(17) C15 0.0144(18) 0.023(2) 0.0191(19) -0.0052(16) 0.0015(15) 0.0023(15) C16 0.020(2) 0.0174(19) 0.0183(18) 0.0005(16) 0.0079(16) 0.0001(15) C17 0.022(2) 0.022(2) 0.0180(18) -0.0043(16) 0.0082(16) 0.0012(16) I11 0.01357(15) 0.03001(18) 0.02883(16) 0.00099(12) 0.00399(12) 0.00059(11) O11 0.0183(15) 0.0290(17) 0.0281(15) 0.0048(13) 0.0091(13) -0.0015(13) O12 0.0157(14) 0.0305(16) 0.0262(14) 0.0074(13) 0.0069(12) 0.0027(12) O13 0.0215(16) 0.038(2) 0.0267(15) 0.0121(14) 0.0084(13) 0.0034(14) C21 0.0164(18) 0.022(2) 0.0175(18) -0.0009(16) 0.0061(15) 0.0017(15) C22 0.0176(19) 0.022(2) 0.0197(18) -0.0057(16) 0.0066(16) -0.0017(15) C23 0.029(2) 0.035(3) 0.024(2) -0.002(2) 0.0149(19) -0.009(2) C24 0.020(2) 0.030(2) 0.028(2) -0.0070(19) 0.0132(18) -0.0047(18) C25 0.0160(19) 0.024(2) 0.024(2) -0.0059(17) 0.0064(16) -0.0008(16) C26 0.017(2) 0.024(2) 0.027(2) -0.0007(18) 0.0078(18) -0.0007(16) C27 0.0178(19) 0.021(2) 0.0194(18) -0.0008(16) 0.0076(16) -0.0009(15) I21 0.01439(15) 0.03003(18) 0.03326(17) -0.00366(12) 0.00362(12) 0.00056(10) O21 0.0177(15) 0.0325(17) 0.0306(16) 0.0101(13) 0.0096(13) 0.0002(13) O22 0.0150(13) 0.0291(16) 0.0244(14) 0.0041(12) 0.0047(12) 0.0009(12) O23 0.0205(17) 0.0321(18) 0.0237(15) 0.0081(13) 0.0072(13) 0.0028(14) _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 C11 C12 1.405(6) . ? C11 C16 1.408(5) . ? C11 C17 1.457(6) . ? C12 O13 1.349(5) . ? C12 C13 1.389(6) . ? C13 C14 1.384(6) . ? C13 H13 0.88(5) . ? C14 C15 1.385(6) . ? C14 H14 0.91(5) . ? C15 C16 1.383(6) . ? C15 I11 2.098(4) . ? C16 H16 1.04(5) . ? C17 O12 1.239(5) . ? C17 O11 1.321(5) . ? O11 H11A 0.78(6) . ? O13 H13A 0.83(6) . ? C21 C22 1.392(6) . ? C21 C26 1.399(5) . ? C21 C27 1.468(5) . ? C22 O23 1.355(5) . ? C22 C23 1.386(6) . ? C23 C24 1.391(6) . ? C23 H23 0.91(5) . ? C24 C25 1.396(6) . ? C24 H24 0.92(5) . ? C25 C26 1.371(6) . ? C25 I21 2.096(4) . ? C26 H26 1.04(5) . ? C27 O22 1.243(5) . ? C27 O21 1.303(5) . ? O21 H21A 0.80(6) . ? O23 H23A 0.68(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C16 119.4(4) . . ? C12 C11 C17 119.8(3) . . ? C16 C11 C17 120.7(4) . . ? O13 C12 C13 117.6(4) . . ? O13 C12 C11 122.8(4) . . ? C13 C12 C11 119.6(4) . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 122(3) . . ? C12 C13 H13 117(3) . . ? C13 C14 C15 119.9(4) . . ? C13 C14 H14 121(3) . . ? C15 C14 H14 119(3) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 I11 118.3(3) . . ? C14 C15 I11 120.9(3) . . ? C15 C16 C11 119.6(4) . . ? C15 C16 H16 121(3) . . ? C11 C16 H16 119(3) . . ? O12 C17 O11 121.9(4) . . ? O12 C17 C11 122.5(4) . . ? O11 C17 C11 115.6(4) . . ? C17 O11 H11A 116(5) . . ? C12 O13 H13A 107(4) . . ? C22 C21 C26 119.9(4) . . ? C22 C21 C27 120.6(3) . . ? C26 C21 C27 119.5(4) . . ? O23 C22 C23 117.1(4) . . ? O23 C22 C21 123.5(4) . . ? C23 C22 C21 119.4(4) . . ? C22 C23 C24 120.7(4) . . ? C22 C23 H23 120(3) . . ? C24 C23 H23 120(3) . . ? C23 C24 C25 119.6(4) . . ? C23 C24 H24 117(3) . . ? C25 C24 H24 124(3) . . ? C26 C25 C24 120.0(4) . . ? C26 C25 I21 119.2(3) . . ? C24 C25 I21 120.8(3) . . ? C25 C26 C21 120.4(4) . . ? C25 C26 H26 116(3) . . ? C21 C26 H26 123(3) . . ? O22 C27 O21 122.9(4) . . ? O22 C27 C21 122.7(4) . . ? O21 C27 C21 114.4(3) . . ? C27 O21 H21A 119(4) . . ? C22 O23 H23A 112(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 O21 H21A O12 0.80(6) 1.87(6) 2.662(4) 166(6) 5_667 O11 H11A O22 0.78(6) 1.91(6) 2.680(4) 173(7) 5_667 O13 H13A O12 0.83(6) 1.85(6) 2.595(4) 149(6) . O23 H23A O22 0.68(5) 2.06(5) 2.641(5) 144(6) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.525 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.130 # Attachment '5-iodosalicylic acid_beta.cif' data_5-iodosalicylic_acid_form_beta _database_code_depnum_ccdc_archive 'CCDC 871039' #TrackingRef '5-iodosalicylic acid_beta.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 I1 O3' _chemical_formula_sum 'C7 H5 I O3' _chemical_formula_weight 264.01 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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8289(1) _cell_length_b 12.1776(3) _cell_length_c 14.6529(4) _cell_angle_alpha 109.752(1) _cell_angle_beta 97.974(2) _cell_angle_gamma 100.626(2) _cell_volume 777.99(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19094 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 4.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6865 _exptl_absorpt_correction_T_max 0.7924 _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 18951 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3566 _reflns_number_gt 3190 _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 ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0167P)^2^+1.1756P] 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 3566 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 C11 C -0.4323(6) 0.1592(3) -0.0517(2) 0.0134(6) Uani 1 1 d . . . C12 C -0.2175(6) 0.2482(3) 0.0265(2) 0.0148(6) Uani 1 1 d . . . H12 H -0.2290 0.2612 0.0934 0.018 Uiso 1 1 calc R . . C13 C 0.0092(6) 0.3163(3) 0.0064(2) 0.0147(6) Uani 1 1 d . . . C14 C 0.0326(6) 0.2952(3) -0.0922(2) 0.0169(6) Uani 1 1 d . . . H14 H 0.1912 0.3416 -0.1057 0.020 Uiso 1 1 calc R . . C15 C -0.1754(7) 0.2070(3) -0.1696(2) 0.0176(6) Uani 1 1 d . . . H15 H -0.1581 0.1923 -0.2363 0.021 Uiso 1 1 calc R . . C16 C -0.4109(6) 0.1395(3) -0.1503(2) 0.0161(6) Uani 1 1 d . . . C17 C -0.6759(6) 0.0888(3) -0.0295(2) 0.0154(6) Uani 1 1 d . . . O11 O -0.6668(4) 0.11157(19) 0.06474(16) 0.0183(4) Uani 1 1 d . . . H11 H -0.8192 0.0718 0.0713 0.027 Uiso 1 1 calc R . . O12 O -0.8774(4) 0.01273(19) -0.09633(16) 0.0184(5) Uani 1 1 d . . . O13 O -0.6118(5) 0.0576(2) -0.22971(16) 0.0215(5) Uani 1 1 d . . . H13 H -0.7420 0.0216 -0.2100 0.032 Uiso 1 1 calc R . . I11 I 0.31432(4) 0.454787(16) 0.123958(14) 0.01741(7) Uani 1 1 d . . . C21 C 1.1050(6) 0.2081(3) 0.5215(2) 0.0171(6) Uani 1 1 d . . . C22 C 1.1195(6) 0.2943(3) 0.6158(2) 0.0163(6) Uani 1 1 d . . . C23 C 0.9615(7) 0.3809(3) 0.6250(2) 0.0210(7) Uani 1 1 d . . . H23A H 0.9688 0.4383 0.6887 0.025 Uiso 1 1 calc R . . C24 C 0.7939(7) 0.3836(3) 0.5415(2) 0.0198(7) Uani 1 1 d . . . H24 H 0.6890 0.4436 0.5478 0.024 Uiso 1 1 calc R . . C25 C 0.7790(6) 0.2980(3) 0.4478(2) 0.0183(6) Uani 1 1 d . . . C26 C 0.9299(6) 0.2107(3) 0.4374(2) 0.0179(6) Uani 1 1 d . . . H26 H 0.9160 0.1521 0.3735 0.021 Uiso 1 1 calc R . . C27 C 1.2743(6) 0.1178(3) 0.5103(2) 0.0171(6) Uani 1 1 d . . . O21 O 1.2359(5) 0.0387(2) 0.41971(16) 0.0228(5) Uani 1 1 d . . . H21 H 1.3399 -0.0095 0.4199 0.034 Uiso 1 1 calc R . . O22 O 1.4425(5) 0.11670(19) 0.58237(16) 0.0196(5) Uani 1 1 d . . . O23 O 1.2817(5) 0.2978(2) 0.70031(16) 0.0217(5) Uani 1 1 d . . . H23 H 1.3622 0.2405 0.6869 0.033 Uiso 1 1 calc R . . I21 I 0.53564(5) 0.305829(19) 0.320294(16) 0.02450(8) 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 C11 0.0148(14) 0.0123(13) 0.0159(15) 0.0074(12) 0.0049(11) 0.0047(11) C12 0.0136(14) 0.0167(14) 0.0152(15) 0.0055(12) 0.0039(11) 0.0062(11) C13 0.0132(14) 0.0138(14) 0.0169(15) 0.0060(12) 0.0018(11) 0.0032(11) C14 0.0154(15) 0.0160(14) 0.0203(16) 0.0078(12) 0.0040(12) 0.0042(11) C15 0.0214(16) 0.0184(15) 0.0140(15) 0.0067(12) 0.0054(12) 0.0051(12) C16 0.0183(15) 0.0150(14) 0.0153(15) 0.0058(12) 0.0033(12) 0.0048(12) C17 0.0147(14) 0.0155(14) 0.0180(15) 0.0075(12) 0.0044(12) 0.0055(12) O11 0.0164(11) 0.0217(11) 0.0162(11) 0.0088(9) 0.0044(8) -0.0002(9) O12 0.0158(11) 0.0204(11) 0.0166(11) 0.0064(9) 0.0033(9) -0.0001(9) O13 0.0183(11) 0.0249(12) 0.0118(11) 0.0022(9) -0.0007(9) -0.0054(9) I11 0.01658(11) 0.01500(11) 0.01704(12) 0.00363(8) 0.00248(8) 0.00072(8) C21 0.0156(15) 0.0155(14) 0.0220(17) 0.0083(13) 0.0077(12) 0.0035(12) C22 0.0156(14) 0.0156(14) 0.0162(15) 0.0047(12) 0.0049(11) 0.0015(11) C23 0.0239(17) 0.0194(15) 0.0165(16) 0.0027(13) 0.0068(13) 0.0040(13) C24 0.0205(16) 0.0167(15) 0.0228(17) 0.0062(13) 0.0069(13) 0.0067(12) C25 0.0193(15) 0.0204(15) 0.0161(16) 0.0095(13) 0.0024(12) 0.0035(12) C26 0.0175(15) 0.0177(15) 0.0161(15) 0.0040(12) 0.0039(12) 0.0032(12) C27 0.0143(14) 0.0153(14) 0.0184(16) 0.0056(12) 0.0025(12) -0.0017(11) O21 0.0245(12) 0.0208(11) 0.0179(12) 0.0004(9) -0.0005(9) 0.0104(9) O22 0.0217(11) 0.0208(11) 0.0166(11) 0.0063(9) 0.0039(9) 0.0079(9) O23 0.0251(12) 0.0257(12) 0.0136(11) 0.0047(9) 0.0025(9) 0.0107(9) I21 0.02588(13) 0.02910(13) 0.02011(13) 0.01125(10) 0.00183(9) 0.00904(10) _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 C11 C16 1.404(4) . ? C11 C12 1.407(4) . ? C11 C17 1.466(4) . ? C12 C13 1.376(4) . ? C12 H12 0.9500 . ? C13 C14 1.405(4) . ? C13 I11 2.097(3) . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.397(4) . ? C15 H15 0.9500 . ? C16 O13 1.355(4) . ? C17 O12 1.247(4) . ? C17 O11 1.306(4) . ? O11 H11 0.8400 . ? O13 H13 0.8400 . ? C21 C22 1.407(4) . ? C21 C26 1.408(4) . ? C21 C27 1.467(4) . ? C22 O23 1.354(4) . ? C22 C23 1.393(4) . ? C23 C24 1.383(5) . ? C23 H23A 0.9500 . ? C24 C25 1.398(4) . ? C24 H24 0.9500 . ? C25 C26 1.376(4) . ? C25 I21 2.105(3) . ? C26 H26 0.9500 . ? C27 O22 1.245(4) . ? C27 O21 1.313(4) . ? O21 H21 0.8400 . ? O23 H23 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 C16 C11 C12 119.4(3) . . ? C16 C11 C17 120.8(3) . . ? C12 C11 C17 119.7(3) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 I11 119.5(2) . . ? C14 C13 I11 120.2(2) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O13 C16 C15 117.2(3) . . ? O13 C16 C11 123.0(3) . . ? C15 C16 C11 119.8(3) . . ? O12 C17 O11 122.6(3) . . ? O12 C17 C11 122.0(3) . . ? O11 C17 C11 115.4(3) . . ? C17 O11 H11 109.5 . . ? C16 O13 H13 109.5 . . ? C22 C21 C26 119.3(3) . . ? C22 C21 C27 120.7(3) . . ? C26 C21 C27 120.1(3) . . ? O23 C22 C23 117.1(3) . . ? O23 C22 C21 123.0(3) . . ? C23 C22 C21 119.9(3) . . ? C24 C23 C22 120.2(3) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 120.0(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.7(3) . . ? C26 C25 I21 119.3(2) . . ? C24 C25 I21 119.9(2) . . ? C25 C26 C21 119.9(3) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? O22 C27 O21 122.6(3) . . ? O22 C27 C21 121.8(3) . . ? O21 C27 C21 115.6(3) . . ? C27 O21 H21 109.5 . . ? C22 O23 H23 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 O21 H21 O22 0.84 1.82 2.656(3) 178.5 2_856 O11 H11 O12 0.84 1.79 2.623(3) 174.3 2_355 O13 H13 O12 0.84 1.90 2.631(3) 144.7 . O23 H23 O22 0.84 1.89 2.623(3) 144.4 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.838 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.135 # Attachment '5-methoxysalicylic_acid.cif' data_5-methoxysalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871040' #TrackingRef '5-methoxysalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-methoxy-2-hydroxobenzoic acid' ; _chemical_name_common '5-methoxysalicylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4' _chemical_formula_sum 'C8 H8 O4' _chemical_formula_weight 168.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0110 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 3.97840(10) _cell_length_b 16.1049(4) _cell_length_c 11.5198(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.261(2) _cell_angle_gamma 90.00 _cell_volume 738.09(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21325 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9411 _exptl_absorpt_correction_T_max 0.9902 _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 11278 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.60 _reflns_number_total 1685 _reflns_number_gt 1582 _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^)+(0.0572P)^2^+0.2285P] 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 1685 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.2307(4) 0.15732(8) 0.67322(11) 0.0175(3) Uani 1 1 d . . . C2 C 0.0461(4) 0.14021(8) 0.77373(12) 0.0196(3) Uani 1 1 d . . . C3 C -0.0462(4) 0.20589(9) 0.84639(12) 0.0216(3) Uani 1 1 d . . . H3A H -0.1704 0.1949 0.9149 0.026 Uiso 1 1 calc R . . C4 C 0.0413(4) 0.28616(9) 0.81951(12) 0.0205(3) Uani 1 1 d . . . H4 H -0.0236 0.3301 0.8697 0.025 Uiso 1 1 calc R . . C5 C 0.2245(4) 0.30400(8) 0.71926(12) 0.0186(3) Uani 1 1 d . . . C6 C 0.3173(4) 0.24013(8) 0.64601(11) 0.0183(3) Uani 1 1 d . . . H6 H 0.4395 0.2519 0.5773 0.022 Uiso 1 1 calc R . . C7 C 0.3371(4) 0.08909(8) 0.59767(12) 0.0189(3) Uani 1 1 d . . . C8 C 0.4732(4) 0.40801(8) 0.59975(13) 0.0238(3) Uani 1 1 d . . . H8A H 0.6909 0.3795 0.5988 0.036 Uiso 1 1 calc R . . H8B H 0.5092 0.4682 0.5979 0.036 Uiso 1 1 calc R . . H8C H 0.3410 0.3912 0.5317 0.036 Uiso 1 1 calc R . . O1 O 0.5265(3) 0.11103(6) 0.50922(9) 0.0240(3) Uani 1 1 d . . . H1 H 0.5839 0.0685 0.4720 0.036 Uiso 1 1 calc R . . O2 O 0.2579(3) 0.01563(6) 0.61548(9) 0.0237(3) Uani 1 1 d . . . O3 O -0.0545(3) 0.06310(6) 0.80632(10) 0.0269(3) Uani 1 1 d . . . H3 H 0.0175 0.0280 0.7586 0.040 Uiso 1 1 calc R . . O4 O 0.2967(3) 0.38636(6) 0.70267(9) 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 C1 0.0206(7) 0.0142(6) 0.0177(6) -0.0006(5) -0.0011(6) 0.0012(5) C2 0.0238(7) 0.0156(6) 0.0196(6) 0.0013(5) 0.0005(6) 0.0001(6) C3 0.0256(7) 0.0206(7) 0.0187(6) -0.0002(5) 0.0038(6) 0.0011(6) C4 0.0242(7) 0.0176(6) 0.0196(6) -0.0033(5) 0.0007(6) 0.0030(5) C5 0.0225(7) 0.0127(6) 0.0207(6) -0.0005(5) -0.0016(6) 0.0002(5) C6 0.0219(7) 0.0156(6) 0.0172(6) -0.0004(5) 0.0012(6) 0.0009(5) C7 0.0218(7) 0.0157(6) 0.0192(6) -0.0002(5) -0.0005(6) 0.0014(5) C8 0.0305(8) 0.0154(6) 0.0257(7) 0.0001(5) 0.0053(7) -0.0017(6) O1 0.0348(6) 0.0136(4) 0.0238(5) -0.0033(4) 0.0102(5) -0.0002(4) O2 0.0329(6) 0.0129(4) 0.0253(5) -0.0012(4) 0.0058(5) -0.0002(4) O3 0.0393(7) 0.0144(5) 0.0271(5) 0.0013(4) 0.0102(5) -0.0017(4) O4 0.0338(6) 0.0114(5) 0.0254(5) -0.0027(4) 0.0068(5) -0.0011(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 1.401(2) . ? C1 C6 1.4130(19) . ? C1 C7 1.4655(18) . ? C2 O3 1.3582(17) . ? C2 C3 1.3989(19) . ? C3 C4 1.374(2) . ? C3 H3A 0.9500 . ? C4 C5 1.398(2) . ? C4 H4 0.9500 . ? C5 O4 1.3708(16) . ? C5 C6 1.3817(19) . ? C6 H6 0.9500 . ? C7 O2 1.2416(17) . ? C7 O1 1.3181(18) . ? C8 O4 1.4239(19) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 H1 0.8400 . ? O3 H3 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 119.88(12) . . ? C2 C1 C7 119.81(12) . . ? C6 C1 C7 120.30(12) . . ? O3 C2 C3 116.59(12) . . ? O3 C2 C1 124.36(12) . . ? C3 C2 C1 119.05(12) . . ? C4 C3 C2 120.60(13) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.85(13) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? O4 C5 C6 125.34(13) . . ? O4 C5 C4 115.11(12) . . ? C6 C5 C4 119.55(12) . . ? C5 C6 C1 120.07(13) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O2 C7 O1 121.97(12) . . ? O2 C7 C1 122.83(13) . . ? O1 C7 C1 115.20(11) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 O1 H1 109.5 . . ? C2 O3 H3 109.5 . . ? C5 O4 C8 117.22(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 1.80 2.6405(14) 173.6 3_656 O3 H3 O2 0.84 1.92 2.6433(15) 143.5 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.222 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.045 data_5-methylsalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-methyl-2-hydroxobenzoic acid' ; _chemical_name_common "'5-methyl-2-hydroxobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O3' _chemical_formula_sum 'C8 H8 O3' _chemical_formula_weight 152.14 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/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 7.2810(3) _cell_length_b 5.0146(2) _cell_length_c 20.2789(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.498(2) _cell_angle_gamma 90.00 _cell_volume 737.00(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12555 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9979 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8182 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1695 _reflns_number_gt 1396 _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^)+(0.0427P)^2^+0.6325P] 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 1695 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.007 _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 0.5901(2) 0.5091(4) 0.39716(8) 0.0212(4) Uani 1 1 d . . . C2 C 0.4557(2) 0.5824(4) 0.34603(9) 0.0231(4) Uani 1 1 d . . . C3 C 0.4918(3) 0.7895(4) 0.30342(9) 0.0251(4) Uani 1 1 d . . . H3 H 0.4012 0.8414 0.2690 0.030 Uiso 1 1 calc R . . C4 C 0.6598(3) 0.9194(4) 0.31131(9) 0.0252(4) Uani 1 1 d . . . H4 H 0.6831 1.0590 0.2816 0.030 Uiso 1 1 calc R . . C5 C 0.7967(2) 0.8516(4) 0.36181(9) 0.0252(4) Uani 1 1 d . . . C6 C 0.7590(2) 0.6474(4) 0.40421(9) 0.0236(4) Uani 1 1 d . . . H6 H 0.8495 0.5992 0.4390 0.028 Uiso 1 1 calc R . . C7 C 0.5538(2) 0.2924(4) 0.44261(8) 0.0220(4) Uani 1 1 d . . . C8 C 0.9790(3) 0.9957(4) 0.36959(11) 0.0351(5) Uani 1 1 d . . . H8A H 1.0225 1.0086 0.4167 0.053 Uiso 1 1 calc R . . H8B H 0.9636 1.1753 0.3508 0.053 Uiso 1 1 calc R . . H8C H 1.0694 0.8971 0.3463 0.053 Uiso 1 1 calc R . . O1 O 0.68545(18) 0.2427(3) 0.48983(6) 0.0268(3) Uani 1 1 d . . . O2 O 0.40615(17) 0.1658(3) 0.43745(6) 0.0255(3) Uani 1 1 d . . . O3 O 0.28927(18) 0.4596(3) 0.33611(7) 0.0305(4) Uani 1 1 d . . . H1A H 0.648(3) 0.105(6) 0.5139(13) 0.049(7) Uiso 1 1 d . . . H3A H 0.290(4) 0.318(6) 0.3676(14) 0.057(8) 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 0.0215(8) 0.0202(8) 0.0221(8) -0.0014(7) 0.0024(7) -0.0022(7) C2 0.0219(9) 0.0233(9) 0.0239(8) -0.0033(7) 0.0009(7) -0.0016(7) C3 0.0274(9) 0.0259(9) 0.0218(8) 0.0015(7) 0.0013(7) 0.0023(7) C4 0.0303(10) 0.0215(9) 0.0248(9) 0.0043(7) 0.0066(7) 0.0002(8) C5 0.0223(9) 0.0245(9) 0.0295(9) 0.0017(8) 0.0051(7) -0.0007(7) C6 0.0208(9) 0.0236(9) 0.0260(9) -0.0003(7) 0.0008(7) -0.0013(7) C7 0.0234(8) 0.0205(9) 0.0218(8) -0.0013(7) 0.0014(7) -0.0002(7) C8 0.0251(10) 0.0326(11) 0.0478(12) 0.0077(10) 0.0049(9) -0.0055(8) O1 0.0257(7) 0.0268(7) 0.0270(7) 0.0061(6) -0.0032(5) -0.0045(6) O2 0.0234(7) 0.0243(7) 0.0282(7) 0.0030(5) -0.0005(5) -0.0052(5) O3 0.0248(7) 0.0327(8) 0.0322(7) 0.0051(6) -0.0064(5) -0.0082(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 C1 C2 1.405(2) . ? C1 C6 1.407(2) . ? C1 C7 1.466(2) . ? C2 O3 1.357(2) . ? C2 C3 1.392(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.401(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(3) . ? C5 C8 1.506(3) . ? C6 H6 0.9500 . ? C7 O2 1.244(2) . ? C7 O1 1.312(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 H1A 0.90(3) . ? O3 H3A 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.10(16) . . ? C2 C1 C7 120.22(15) . . ? C6 C1 C7 120.68(16) . . ? O3 C2 C3 117.75(16) . . ? O3 C2 C1 122.67(16) . . ? C3 C2 C1 119.58(16) . . ? C4 C3 C2 119.84(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 122.05(17) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 117.69(17) . . ? C6 C5 C8 121.07(17) . . ? C4 C5 C8 121.24(17) . . ? C5 C6 C1 121.74(17) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? O2 C7 O1 121.97(16) . . ? O2 C7 C1 122.13(15) . . ? O1 C7 C1 115.89(15) . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 O1 H1A 107.8(16) . . ? C2 O3 H3A 106.8(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 O3 -179.74(16) . . . . ? C7 C1 C2 O3 -0.1(3) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? C7 C1 C2 C3 179.71(16) . . . . ? O3 C2 C3 C4 -179.60(16) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C8 -179.99(18) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C8 C5 C6 C1 -179.34(18) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C7 C1 C6 C5 179.70(16) . . . . ? C2 C1 C7 O2 0.6(3) . . . . ? C6 C1 C7 O2 -179.72(17) . . . . ? C2 C1 C7 O1 -178.28(16) . . . . ? C6 C1 C7 O1 1.4(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 H1A O2 0.90(3) 1.75(3) 2.6467(18) 176(2) 3_656 O3 H3A O2 0.96(3) 1.75(3) 2.6043(19) 147(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.272 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.054 # Attachment '5-nitrosalicylic_acid.cif' data_5-nitrosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871042' #TrackingRef '5-nitrosalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-nitro-2-hydroxobenzoic acid monohydrate' ; _chemical_name_common '5-nitrosalicylic acid monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N O5' _chemical_formula_sum 'C7 H5 N O5' _chemical_formula_weight 183.12 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1246(5) _cell_length_b 8.7762(8) _cell_length_c 9.2674(9) _cell_angle_alpha 62.252(6) _cell_angle_beta 75.292(6) _cell_angle_gamma 82.654(7) _cell_volume 356.76(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12477 _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 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9497 _exptl_absorpt_correction_T_max 0.9882 _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 6568 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1634 _reflns_number_gt 1204 _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^)+(0.0721P)^2^+0.0356P] 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 1634 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1115 _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 0.0636(3) 0.2073(2) 0.6958(2) 0.0172(4) Uani 1 1 d . . . C2 C -0.1470(3) 0.3098(2) 0.6239(2) 0.0187(4) Uani 1 1 d . . . C3 C -0.3179(3) 0.4017(2) 0.7013(2) 0.0201(4) Uani 1 1 d . . . H3A H -0.4608 0.4703 0.6529 0.024 Uiso 1 1 calc R . . C4 C -0.2803(3) 0.3932(2) 0.8460(2) 0.0204(4) Uani 1 1 d . . . H4 H -0.3945 0.4567 0.8974 0.025 Uiso 1 1 calc R . . C5 C -0.0717(3) 0.2900(2) 0.9168(2) 0.0178(4) Uani 1 1 d . . . C6 C 0.0997(3) 0.1979(2) 0.8444(2) 0.0176(4) Uani 1 1 d . . . H6 H 0.2405 0.1288 0.8949 0.021 Uiso 1 1 calc R . . C7 C 0.2488(3) 0.1118(2) 0.6148(2) 0.0178(4) Uani 1 1 d . . . N1 N -0.0316(3) 0.27943(18) 1.07170(18) 0.0201(4) Uani 1 1 d . . . O1 O 0.4211(2) 0.01033(15) 0.70114(14) 0.0218(3) Uani 1 1 d . . . H1 H 0.5269 -0.0336 0.6449 0.033 Uiso 1 1 calc R . . O2 O 0.2364(3) 0.12873(16) 0.47645(15) 0.0234(3) Uani 1 1 d . . . O3 O -0.1973(2) 0.32609(16) 0.48157(15) 0.0221(3) Uani 1 1 d . . . H3 H -0.0784 0.2724 0.4415 0.033 Uiso 1 1 calc R . . O4 O -0.1897(2) 0.35833(16) 1.13839(15) 0.0265(3) Uani 1 1 d . . . O5 O 0.1568(3) 0.19136(17) 1.12958(16) 0.0294(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 0.0185(8) 0.0175(8) 0.0169(8) -0.0094(7) -0.0033(7) 0.0012(7) C2 0.0197(8) 0.0201(9) 0.0169(8) -0.0082(7) -0.0047(7) -0.0011(7) C3 0.0184(9) 0.0225(9) 0.0202(9) -0.0108(7) -0.0067(7) 0.0063(7) C4 0.0201(9) 0.0219(9) 0.0212(9) -0.0132(7) -0.0028(7) 0.0036(7) C5 0.0214(9) 0.0198(9) 0.0145(8) -0.0097(7) -0.0042(7) 0.0007(7) C6 0.0168(8) 0.0176(8) 0.0190(9) -0.0086(7) -0.0059(7) 0.0032(7) C7 0.0181(8) 0.0193(8) 0.0168(8) -0.0091(7) -0.0042(7) 0.0009(7) N1 0.0236(8) 0.0207(7) 0.0174(7) -0.0111(6) -0.0035(6) 0.0025(6) O1 0.0231(7) 0.0251(7) 0.0205(6) -0.0140(5) -0.0081(5) 0.0107(5) O2 0.0278(7) 0.0281(7) 0.0198(6) -0.0157(5) -0.0087(5) 0.0086(5) O3 0.0229(7) 0.0301(7) 0.0192(6) -0.0156(5) -0.0088(5) 0.0070(5) O4 0.0321(8) 0.0295(7) 0.0232(7) -0.0187(6) -0.0046(6) 0.0066(6) O5 0.0324(8) 0.0383(8) 0.0249(7) -0.0189(6) -0.0155(6) 0.0121(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.399(2) . ? C1 C2 1.406(2) . ? C1 C7 1.479(2) . ? C2 O3 1.347(2) . ? C2 C3 1.404(2) . ? C3 C4 1.369(2) . ? C3 H3A 0.9500 . ? C4 C5 1.396(2) . ? C4 H4 0.9500 . ? C5 C6 1.378(2) . ? C5 N1 1.460(2) . ? C6 H6 0.9500 . ? C7 O2 1.238(2) . ? C7 O1 1.3063(19) . ? N1 O5 1.2258(18) . ? N1 O4 1.2324(18) . ? O1 H1 0.8400 . ? O3 H3 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 119.41(15) . . ? C6 C1 C7 119.87(15) . . ? C2 C1 C7 120.72(15) . . ? O3 C2 C3 116.68(15) . . ? O3 C2 C1 123.50(15) . . ? C3 C2 C1 119.82(15) . . ? C4 C3 C2 120.56(15) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.06(15) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.99(15) . . ? C6 C5 N1 118.65(15) . . ? C4 C5 N1 119.36(14) . . ? C5 C6 C1 119.16(15) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 123.96(14) . . ? O2 C7 C1 121.41(14) . . ? O1 C7 C1 114.62(14) . . ? O5 N1 O4 123.26(14) . . ? O5 N1 C5 118.29(13) . . ? O4 N1 C5 118.44(14) . . ? C7 O1 H1 109.5 . . ? C2 O3 H3 109.5 . . ? 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 -179.77(15) . . . . ? C7 C1 C2 O3 1.1(3) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 -178.96(15) . . . . ? O3 C2 C3 C4 -179.64(16) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C3 C4 C5 N1 -179.57(15) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? N1 C5 C6 C1 -179.85(14) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C7 C1 C6 C5 178.87(16) . . . . ? C6 C1 C7 O2 -173.92(16) . . . . ? C2 C1 C7 O2 5.3(3) . . . . ? C6 C1 C7 O1 6.3(2) . . . . ? C2 C1 C7 O1 -174.51(15) . . . . ? C6 C5 N1 O5 1.4(2) . . . . ? C4 C5 N1 O5 -178.27(16) . . . . ? C6 C5 N1 O4 -178.07(15) . . . . ? C4 C5 N1 O4 2.3(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 1.83 2.6711(16) 178.8 2_656 O3 H3 O2 0.84 1.91 2.6421(16) 144.3 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.368 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.070 # Attachment '5chlorosalicylic_acid.cif' data_5-chlorosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871043' #TrackingRef '5chlorosalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-chloro-2-hydroxobenzoic acid' ; _chemical_name_common 5-chlorosalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Cl O3' _chemical_formula_sum 'C7 H5 Cl O3' _chemical_formula_weight 172.56 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 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 23.3708(10) _cell_length_b 3.70890(10) _cell_length_c 16.5722(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.853(2) _cell_angle_gamma 90.00 _cell_volume 1388.48(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2942 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8989 _exptl_absorpt_correction_T_max 0.9805 _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 9922 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3153 _reflns_number_gt 2188 _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^)+(0.0322P)^2^+1.1165P] 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 0.0046(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3153 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.10417(12) 0.4524(7) 0.18588(16) 0.0185(6) Uani 1 1 d . . . C2 C 0.16003(12) 0.3136(7) 0.18600(16) 0.0192(6) Uani 1 1 d . . . C3 C 0.20412(12) 0.3042(7) 0.26046(17) 0.0203(6) Uani 1 1 d . . . H3 H 0.2422 0.2128 0.2609 0.024 Uiso 1 1 calc R . . C4 C 0.19319(13) 0.4255(7) 0.33315(17) 0.0231(6) Uani 1 1 d . . . H4 H 0.2235 0.4183 0.3838 0.028 Uiso 1 1 calc R . . C5 C 0.13739(12) 0.5593(7) 0.33251(16) 0.0194(6) Uani 1 1 d . . . C6 C 0.09349(12) 0.5756(7) 0.26046(16) 0.0191(6) Uani 1 1 d . . . H6 H 0.0558 0.6702 0.2608 0.023 Uiso 1 1 calc R . . C7 C 0.05798(12) 0.4724(7) 0.10733(16) 0.0194(6) Uani 1 1 d . . . O1 O 0.00882(9) 0.6347(5) 0.11228(12) 0.0255(5) Uani 1 1 d . . . H1 H -0.0146 0.6461 0.0646 0.038 Uiso 1 1 calc R . . O2 O 0.06472(9) 0.3486(5) 0.04145(11) 0.0241(4) Uani 1 1 d . . . O3 O 0.17377(9) 0.1849(5) 0.11712(12) 0.0242(4) Uani 1 1 d . . . H3A H 0.1444 0.2073 0.0758 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.12450(3) 0.71135(18) 0.42532(4) 0.0240(2) Uani 1 1 d . . . C21 C 0.39036(12) 0.3745(7) 0.07310(16) 0.0189(6) Uani 1 1 d . . . C22 C 0.33510(12) 0.4303(7) 0.01678(16) 0.0205(6) Uani 1 1 d . . . C23 C 0.28955(13) 0.5765(7) 0.04515(18) 0.0233(6) Uani 1 1 d . . . H23 H 0.2520 0.6139 0.0071 0.028 Uiso 1 1 calc R . . C24 C 0.29759(13) 0.6683(7) 0.12710(17) 0.0224(6) Uani 1 1 d . . . H24 H 0.2659 0.7685 0.1458 0.027 Uiso 1 1 calc R . . C25 C 0.35228(12) 0.6146(7) 0.18288(16) 0.0204(6) Uani 1 1 d . . . C26 C 0.39850(12) 0.4687(7) 0.15705(17) 0.0206(6) Uani 1 1 d . . . H26 H 0.4357 0.4318 0.1958 0.025 Uiso 1 1 calc R . . C27 C 0.43872(13) 0.2148(7) 0.04418(17) 0.0220(6) Uani 1 1 d . . . O21 O 0.43297(9) 0.1235(5) -0.02930(12) 0.0270(5) Uani 1 1 d . . . O22 O 0.48866(9) 0.1718(6) 0.10122(12) 0.0288(5) Uani 1 1 d . . . H22 H 0.5143 0.0877 0.0790 0.043 Uiso 1 1 calc R . . O23 O 0.32352(9) 0.3462(5) -0.06506(11) 0.0265(5) Uani 1 1 d . . . H23A H 0.3541 0.2598 -0.0755 0.040 Uiso 1 1 calc R . . Cl2 Cl 0.36170(3) 0.73806(18) 0.28655(4) 0.0282(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 0.0193(14) 0.0166(13) 0.0202(14) -0.0003(10) 0.0060(12) -0.0017(10) C2 0.0215(15) 0.0158(13) 0.0227(14) 0.0013(10) 0.0102(12) -0.0028(10) C3 0.0148(14) 0.0214(14) 0.0247(14) 0.0012(11) 0.0049(11) 0.0012(10) C4 0.0218(15) 0.0232(15) 0.0236(15) 0.0008(11) 0.0046(12) -0.0013(11) C5 0.0247(15) 0.0161(13) 0.0185(13) 0.0006(10) 0.0075(12) -0.0026(11) C6 0.0210(14) 0.0180(14) 0.0189(13) 0.0014(10) 0.0063(12) -0.0003(10) C7 0.0186(14) 0.0201(14) 0.0205(14) 0.0032(10) 0.0070(12) -0.0002(11) O1 0.0194(11) 0.0374(11) 0.0190(10) -0.0028(9) 0.0035(8) 0.0063(9) O2 0.0234(11) 0.0326(11) 0.0170(10) -0.0019(8) 0.0064(8) 0.0038(8) O3 0.0215(11) 0.0324(11) 0.0200(10) -0.0019(8) 0.0076(8) 0.0040(9) Cl1 0.0279(4) 0.0274(4) 0.0176(3) -0.0017(3) 0.0075(3) 0.0007(3) C21 0.0206(15) 0.0165(13) 0.0221(14) 0.0024(10) 0.0097(12) 0.0015(10) C22 0.0209(15) 0.0209(14) 0.0198(14) 0.0036(11) 0.0056(12) -0.0016(11) C23 0.0180(14) 0.0255(15) 0.0266(15) 0.0026(11) 0.0065(12) 0.0020(11) C24 0.0232(16) 0.0210(14) 0.0266(15) 0.0031(11) 0.0126(13) 0.0006(11) C25 0.0234(15) 0.0198(14) 0.0198(14) 0.0016(10) 0.0088(12) 0.0001(11) C26 0.0206(15) 0.0207(14) 0.0209(14) 0.0019(10) 0.0063(12) 0.0002(11) C27 0.0208(15) 0.0236(14) 0.0230(14) -0.0002(11) 0.0080(12) -0.0022(11) O21 0.0224(11) 0.0365(12) 0.0232(11) -0.0040(8) 0.0077(9) 0.0052(9) O22 0.0179(11) 0.0454(13) 0.0241(11) -0.0057(9) 0.0071(9) 0.0079(9) O23 0.0225(11) 0.0374(12) 0.0197(10) -0.0028(8) 0.0056(9) 0.0025(9) Cl2 0.0369(5) 0.0292(4) 0.0213(4) -0.0021(3) 0.0128(3) 0.0035(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.399(3) . ? C1 C2 1.403(4) . ? C1 C7 1.465(4) . ? C2 O3 1.350(3) . ? C2 C3 1.391(4) . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(4) . ? C4 H4 0.9500 . ? C5 C6 1.362(4) . ? C5 Cl1 1.735(3) . ? C6 H6 0.9500 . ? C7 O2 1.231(3) . ? C7 O1 1.318(3) . ? O1 H1 0.8400 . ? O3 H3A 0.8400 . ? C21 C26 1.399(4) . ? C21 C22 1.401(4) . ? C21 C27 1.461(4) . ? C22 O23 1.350(3) . ? C22 C23 1.380(4) . ? C23 C24 1.366(4) . ? C23 H23 0.9500 . ? C24 C25 1.386(4) . ? C24 H24 0.9500 . ? C25 C26 1.371(4) . ? C25 Cl2 1.736(3) . ? C26 H26 0.9500 . ? C27 O21 1.238(3) . ? C27 O22 1.310(3) . ? O22 H22 0.8400 . ? O23 H23A 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 119.7(2) . . ? C6 C1 C7 120.7(2) . . ? C2 C1 C7 119.6(2) . . ? O3 C2 C3 117.3(2) . . ? O3 C2 C1 123.5(2) . . ? C3 C2 C1 119.2(2) . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 121.1(2) . . ? C6 C5 Cl1 120.0(2) . . ? C4 C5 Cl1 118.9(2) . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? O2 C7 O1 122.5(2) . . ? O2 C7 C1 122.4(2) . . ? O1 C7 C1 115.1(2) . . ? C7 O1 H1 109.5 . . ? C2 O3 H3A 109.5 . . ? C26 C21 C22 119.5(2) . . ? C26 C21 C27 120.5(2) . . ? C22 C21 C27 120.0(2) . . ? O23 C22 C23 117.4(2) . . ? O23 C22 C21 123.3(2) . . ? C23 C22 C21 119.4(2) . . ? C24 C23 C22 121.0(3) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 120.9(2) . . ? C26 C25 Cl2 120.2(2) . . ? C24 C25 Cl2 118.9(2) . . ? C25 C26 C21 119.5(3) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? O21 C27 O22 121.9(3) . . ? O21 C27 C21 122.4(3) . . ? O22 C27 C21 115.7(2) . . ? C27 O22 H22 109.5 . . ? C22 O23 H23A 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 O3 H3A O2 0.84 1.88 2.607(3) 144.5 . O23 H23A O21 0.84 1.88 2.608(3) 144.8 . O1 H1 O2 0.84 1.84 2.684(3) 177.4 3_565 O3 H3A Cl1 0.84 2.87 3.422(2) 124.8 4_565 O23 H23A Cl2 0.84 2.98 3.559(2) 128.0 4_565 O22 H22 O21 0.84 1.82 2.663(3) 176.0 3_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.414 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.081 data_5-chlorosalicylic_acid_monohydrate _database_code_depnum_ccdc_archive 'CCDC 871044' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-chloro-2-hydroxobenzoic acid monohydrate' ; _chemical_name_common "'5-chloro-2-hydroxobenzoic acid monohydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Cl O3, H2 O' _chemical_formula_sum 'C7 H7 Cl O4' _chemical_formula_weight 190.58 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.72890(10) _cell_length_b 8.2430(4) _cell_length_c 13.0565(7) _cell_angle_alpha 80.768(2) _cell_angle_beta 87.719(3) _cell_angle_gamma 83.755(3) _cell_volume 393.67(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6550 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.454 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8394 _exptl_absorpt_correction_T_max 0.9434 _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 7078 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1796 _reflns_number_gt 1643 _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^)+(0.0336P)^2^+0.1787P] 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 1796 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 H3 H 0.682(5) 1.136(2) 0.2489(14) 0.023(4) Uiso 1 1 d . . . H3A H 0.378(6) 0.920(3) 0.0791(19) 0.052(7) Uiso 1 1 d . . . H4 H 0.819(5) 1.021(2) 0.4210(13) 0.021(4) Uiso 1 1 d . . . H4A H 0.193(6) 0.227(3) 0.0983(17) 0.045(6) Uiso 1 1 d . . . H4B H -0.033(6) 0.337(3) 0.0447(18) 0.039(6) Uiso 1 1 d . . . H6 H 0.566(4) 0.573(2) 0.3712(13) 0.022(4) Uiso 1 1 d . . . H1A H 0.229(7) 0.443(3) 0.1726(19) 0.056(7) Uiso 1 1 d . . . C1 C 0.4954(3) 0.75304(16) 0.24461(10) 0.0127(3) Uani 1 1 d . . . C2 C 0.5317(3) 0.92097(17) 0.20883(10) 0.0143(3) Uani 1 1 d . . . C3 C 0.6513(4) 1.01926(17) 0.27513(11) 0.0158(3) Uani 1 1 d . . . C4 C 0.7350(3) 0.95172(17) 0.37649(11) 0.0147(3) Uani 1 1 d . . . C5 C 0.7023(3) 0.78515(16) 0.41157(10) 0.0128(3) Uani 1 1 d . . . C6 C 0.5837(3) 0.68556(16) 0.34723(10) 0.0132(3) Uani 1 1 d . . . C7 C 0.3558(3) 0.65132(16) 0.17476(10) 0.0148(3) Uani 1 1 d . . . O1 O 0.3223(3) 0.49779(12) 0.21598(8) 0.0204(2) Uani 1 1 d . . . O2 O 0.2738(3) 0.70866(12) 0.08455(8) 0.0217(2) Uani 1 1 d . . . O3 O 0.4519(3) 0.99381(13) 0.10998(8) 0.0198(2) Uani 1 1 d . . . O4 O 0.0703(3) 0.31578(14) 0.09894(9) 0.0241(3) Uani 1 1 d . . . Cl1 Cl 0.81380(8) 0.70188(4) 0.53879(2) 0.01680(12) 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 0.0118(6) 0.0140(6) 0.0133(6) -0.0052(5) 0.0005(5) -0.0015(5) C2 0.0144(6) 0.0161(6) 0.0124(6) -0.0029(5) 0.0002(5) -0.0008(5) C3 0.0172(7) 0.0133(6) 0.0176(7) -0.0034(5) 0.0005(5) -0.0038(5) C4 0.0136(6) 0.0164(6) 0.0162(7) -0.0074(5) -0.0010(5) -0.0033(5) C5 0.0115(6) 0.0153(6) 0.0119(6) -0.0025(5) -0.0008(4) -0.0014(5) C6 0.0125(6) 0.0121(6) 0.0155(6) -0.0039(5) 0.0005(5) -0.0019(5) C7 0.0143(6) 0.0161(6) 0.0150(7) -0.0059(5) -0.0003(5) -0.0011(5) O1 0.0323(6) 0.0139(5) 0.0168(5) -0.0045(4) -0.0064(4) -0.0057(4) O2 0.0323(6) 0.0200(5) 0.0140(5) -0.0038(4) -0.0066(4) -0.0053(4) O3 0.0315(6) 0.0152(5) 0.0133(5) -0.0012(4) -0.0047(4) -0.0051(4) O4 0.0346(6) 0.0180(5) 0.0220(6) -0.0085(4) -0.0125(5) -0.0009(5) Cl1 0.0213(2) 0.01722(18) 0.01276(18) -0.00278(12) -0.00505(12) -0.00359(12) _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 C6 1.4033(18) . ? C1 C2 1.4075(18) . ? C1 C7 1.4777(18) . ? C2 O3 1.3630(16) . ? C2 C3 1.3924(19) . ? C3 C4 1.3848(19) . ? C3 H3 0.985(18) . ? C4 C5 1.3928(19) . ? C4 H4 0.959(18) . ? C5 C6 1.3802(18) . ? C5 Cl1 1.7407(13) . ? C6 H6 0.936(18) . ? C7 O2 1.2340(17) . ? C7 O1 1.3105(16) . ? O1 H1A 0.88(3) . ? O3 H3A 0.86(3) . ? O4 H4A 0.82(2) . ? O4 H4B 0.81(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 C6 C1 C2 119.40(12) . . ? C6 C1 C7 120.88(12) . . ? C2 C1 C7 119.71(12) . . ? O3 C2 C3 117.55(12) . . ? O3 C2 C1 122.29(12) . . ? C3 C2 C1 120.15(12) . . ? C4 C3 C2 119.97(12) . . ? C4 C3 H3 120.5(10) . . ? C2 C3 H3 119.6(10) . . ? C3 C4 C5 119.85(12) . . ? C3 C4 H4 118.9(10) . . ? C5 C4 H4 121.2(10) . . ? C6 C5 C4 121.14(12) . . ? C6 C5 Cl1 119.67(10) . . ? C4 C5 Cl1 119.20(10) . . ? C5 C6 C1 119.49(12) . . ? C5 C6 H6 120.5(11) . . ? C1 C6 H6 120.0(11) . . ? O2 C7 O1 122.92(12) . . ? O2 C7 C1 121.88(12) . . ? O1 C7 C1 115.20(12) . . ? C7 O1 H1A 112.1(16) . . ? C2 O3 H3A 107.1(16) . . ? H4A O4 H4B 107(2) . . ? 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 179.71(11) . . . . ? C7 C1 C2 O3 -1.94(19) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? C7 C1 C2 C3 177.80(12) . . . . ? O3 C2 C3 C4 179.81(12) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.7(2) . . . . ? C3 C4 C5 Cl1 179.27(10) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? Cl1 C5 C6 C1 -179.77(9) . . . . ? C2 C1 C6 C5 0.44(19) . . . . ? C7 C1 C6 C5 -177.89(11) . . . . ? C6 C1 C7 O2 179.40(12) . . . . ? C2 C1 C7 O2 1.1(2) . . . . ? C6 C1 C7 O1 0.14(18) . . . . ? C2 C1 C7 O1 -178.18(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 O4 H4A O3 0.82(2) 2.04(2) 2.8568(16) 173(2) 1_545 O4 H4B O2 0.81(2) 2.05(2) 2.8077(15) 157(2) 2_565 O1 H1A O4 0.88(3) 1.70(3) 2.5739(14) 173(2) . O3 H3A O2 0.86(3) 1.81(2) 2.5854(14) 149(2) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.263 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.057 # Attachment '6-fluorosalicylic_acid.cif' data_6-fluorosalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871045' #TrackingRef '6-fluorosalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '6-fluoro-2-hydroxobenzoic acid' ; _chemical_name_common 6-fluorosalicylic_acid _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 F O3' _chemical_formula_sum 'C7 H5 F O3' _chemical_formula_weight 156.11 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 P21/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 5.3146(2) _cell_length_b 5.2118(2) _cell_length_c 22.5378(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.907(3) _cell_angle_gamma 90.00 _cell_volume 623.92(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21229 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9566 _exptl_absorpt_correction_T_max 0.9985 _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 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 8172 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1420 _reflns_number_gt 1212 _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^)+(0.0587P)^2^+0.3464P] 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 1420 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0469(3) 0.9619(3) 0.10787(7) 0.0210(4) Uani 1 1 d . . . C2 C 1.2474(3) 1.1389(3) 0.10621(7) 0.0247(4) Uani 1 1 d . . . C3 C 1.2808(3) 1.3264(3) 0.15005(9) 0.0297(4) Uani 1 1 d . . . H3 H 1.4165 1.4445 0.1484 0.036 Uiso 1 1 calc R . . C4 C 1.1151(3) 1.3381(3) 0.19558(8) 0.0300(4) Uani 1 1 d . . . H4 H 1.1373 1.4665 0.2252 0.036 Uiso 1 1 calc R . . C5 C 0.9159(3) 1.1663(3) 0.19927(7) 0.0266(4) Uani 1 1 d . . . H5 H 0.8039 1.1748 0.2312 0.032 Uiso 1 1 calc R . . C6 C 0.8850(3) 0.9835(3) 0.15545(7) 0.0219(4) Uani 1 1 d . . . C7 C 1.0154(3) 0.7641(3) 0.06113(7) 0.0228(4) Uani 1 1 d . . . O1 O 0.8203(3) 0.6151(3) 0.06338(6) 0.0320(3) Uani 1 1 d . . . O2 O 1.1737(3) 0.7462(3) 0.02162(5) 0.0359(4) Uani 1 1 d . . . O3 O 1.4152(3) 1.1392(3) 0.06271(7) 0.0339(4) Uani 1 1 d . . . F1 F 0.68973(19) 0.8194(2) 0.16084(5) 0.0324(3) Uani 1 1 d . . . H1A H 0.825(6) 0.505(7) 0.0383(15) 0.081(10) Uiso 1 1 d . . . H3A H 1.382(6) 1.043(6) 0.0456(15) 0.075(12) 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 0.0244(8) 0.0183(7) 0.0201(7) 0.0001(6) -0.0038(6) 0.0021(6) C2 0.0212(8) 0.0263(8) 0.0266(8) 0.0042(6) -0.0007(6) 0.0004(6) C3 0.0244(8) 0.0219(8) 0.0422(10) -0.0005(7) -0.0086(7) -0.0022(6) C4 0.0334(9) 0.0217(8) 0.0338(9) -0.0075(7) -0.0129(7) 0.0047(7) C5 0.0302(8) 0.0269(9) 0.0227(8) -0.0022(6) -0.0014(6) 0.0051(7) C6 0.0219(7) 0.0197(7) 0.0239(8) 0.0035(6) -0.0022(6) -0.0016(6) C7 0.0267(8) 0.0226(8) 0.0191(7) 0.0004(6) -0.0019(6) 0.0035(6) O1 0.0399(7) 0.0258(7) 0.0298(7) -0.0081(5) -0.0059(5) -0.0041(5) O2 0.0436(8) 0.0375(8) 0.0267(7) -0.0083(6) 0.0038(5) 0.0046(6) O3 0.0240(7) 0.0432(9) 0.0348(8) 0.0030(6) 0.0070(5) -0.0061(6) F1 0.0332(6) 0.0308(6) 0.0334(6) 0.0008(4) 0.0049(4) -0.0093(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 1.401(2) . ? C1 C2 1.411(2) . ? C1 C7 1.480(2) . ? C2 O3 1.347(2) . ? C2 C3 1.397(2) . ? C3 C4 1.376(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 H4 0.9500 . ? C5 C6 1.378(2) . ? C5 H5 0.9500 . ? C6 F1 1.3533(18) . ? C7 O2 1.249(2) . ? C7 O1 1.298(2) . ? O1 H1A 0.81(3) . ? O3 H3A 0.65(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 C6 C1 C2 116.82(14) . . ? C6 C1 C7 122.90(14) . . ? C2 C1 C7 120.28(15) . . ? O3 C2 C3 116.24(16) . . ? O3 C2 C1 122.63(16) . . ? C3 C2 C1 121.13(16) . . ? C4 C3 C2 119.30(16) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.55(16) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 118.34(16) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? F1 C6 C5 116.48(15) . . ? F1 C6 C1 120.67(14) . . ? C5 C6 C1 122.85(15) . . ? O2 C7 O1 122.78(15) . . ? O2 C7 C1 119.80(15) . . ? O1 C7 C1 117.42(14) . . ? C7 O1 H1A 111(2) . . ? C2 O3 H3A 105(3) . . ? 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 O3 H3A O2 0.65(3) 1.97(3) 2.573(2) 155(4) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.296 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.056 # Attachment '6-methoxysalicylic_acid.cif' data_6-methoxysalicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871046' #TrackingRef '6-methoxysalicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '6-methoxy-2-hydroxobenzoic acid' ; _chemical_name_common '6-methoxysalicylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4' _chemical_formula_sum 'C8 H8 O4' _chemical_formula_weight 168.14 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/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 6.6697(2) _cell_length_b 9.3476(4) _cell_length_c 12.2016(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.305(2) _cell_angle_gamma 90.00 _cell_volume 737.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6881 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9902 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7885 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1678 _reflns_number_gt 1445 _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^)+(0.0639P)^2^+0.4686P] 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 1678 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1491 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _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 H1A H 0.799(4) 0.678(3) 0.199(2) 0.060(8) Uiso 1 1 d . . . H3 H 0.683(3) 0.282(3) -0.1669(19) 0.032(6) Uiso 1 1 d . . . H3A H 0.807(5) 0.252(4) 0.121(3) 0.088(11) Uiso 1 1 d . . . H4 H 0.632(4) 0.511(2) -0.260(2) 0.038(7) Uiso 1 1 d . . . H5 H 0.681(3) 0.727(2) -0.1543(19) 0.031(6) Uiso 1 1 d . . . H8A H 0.753(3) 0.952(2) 0.0676(18) 0.022(5) Uiso 1 1 d . . . H8B H 0.851(3) 0.905(2) -0.0307(17) 0.027(5) Uiso 1 1 d . . . H8C H 0.605(3) 0.894(2) -0.0411(18) 0.030(6) Uiso 1 1 d . . . C1 C 0.7743(2) 0.49498(16) 0.05525(13) 0.0145(4) Uani 1 1 d . . . C2 C 0.7512(2) 0.36787(18) -0.00885(14) 0.0173(4) Uani 1 1 d . . . C3 C 0.6996(2) 0.37301(19) -0.12739(14) 0.0213(4) Uani 1 1 d . . . C4 C 0.6729(3) 0.50369(19) -0.18072(14) 0.0215(4) Uani 1 1 d . . . C5 C 0.6962(2) 0.63248(19) -0.12094(13) 0.0195(4) Uani 1 1 d . . . C6 C 0.7463(2) 0.62729(17) -0.00337(13) 0.0151(4) Uani 1 1 d . . . C7 C 0.8246(2) 0.48376(17) 0.17961(14) 0.0160(4) Uani 1 1 d . . . C8 C 0.7403(3) 0.88537(18) 0.00905(16) 0.0230(4) Uani 1 1 d . . . O1 O 0.83705(19) 0.60101(13) 0.24274(10) 0.0215(3) Uani 1 1 d . . . O2 O 0.85373(18) 0.36819(13) 0.22866(10) 0.0217(3) Uani 1 1 d . . . O3 O 0.77577(19) 0.23747(13) 0.03953(11) 0.0234(3) Uani 1 1 d . . . O4 O 0.77077(18) 0.74721(12) 0.06202(10) 0.0202(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 0.0117(7) 0.0167(9) 0.0156(8) -0.0004(5) 0.0043(6) -0.0002(5) C2 0.0130(7) 0.0176(8) 0.0220(8) -0.0011(6) 0.0056(6) -0.0009(5) C3 0.0194(8) 0.0246(9) 0.0205(8) -0.0081(7) 0.0063(6) -0.0021(6) C4 0.0192(8) 0.0308(10) 0.0142(8) -0.0023(6) 0.0032(6) -0.0013(6) C5 0.0185(8) 0.0234(9) 0.0170(8) 0.0038(6) 0.0049(6) 0.0017(6) C6 0.0127(7) 0.0166(8) 0.0165(7) -0.0016(6) 0.0042(5) 0.0003(5) C7 0.0149(7) 0.0158(8) 0.0175(8) 0.0010(6) 0.0042(6) 0.0008(5) C8 0.0292(9) 0.0128(8) 0.0264(9) 0.0029(7) 0.0058(7) 0.0013(6) O1 0.0302(6) 0.0177(6) 0.0150(6) -0.0008(5) 0.0028(5) 0.0012(5) O2 0.0268(6) 0.0179(6) 0.0203(6) 0.0053(5) 0.0054(5) 0.0015(5) O3 0.0293(7) 0.0144(6) 0.0274(7) -0.0012(5) 0.0087(5) -0.0003(4) O4 0.0295(6) 0.0131(6) 0.0178(6) 0.0016(4) 0.0057(5) 0.0023(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 1.410(2) . ? C1 C6 1.418(2) . ? C1 C7 1.475(2) . ? C2 O3 1.347(2) . ? C2 C3 1.402(2) . ? C3 C4 1.375(3) . ? C3 H3 0.97(2) . ? C4 C5 1.396(2) . ? C4 H4 0.94(3) . ? C5 C6 1.391(2) . ? C5 H5 0.96(2) . ? C6 O4 1.3621(18) . ? C7 O2 1.2270(19) . ? C7 O1 1.3304(19) . ? C8 O4 1.4359(19) . ? C8 H8A 0.94(2) . ? C8 H8B 0.99(2) . ? C8 H8C 0.96(2) . ? O1 H1A 0.89(3) . ? O3 H3A 0.97(4) . ? 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 118.20(14) . . ? C2 C1 C7 118.48(14) . . ? C6 C1 C7 123.32(14) . . ? O3 C2 C3 117.09(15) . . ? O3 C2 C1 122.34(14) . . ? C3 C2 C1 120.58(15) . . ? C4 C3 C2 119.25(16) . . ? C4 C3 H3 123.9(13) . . ? C2 C3 H3 116.8(13) . . ? C3 C4 C5 122.29(15) . . ? C3 C4 H4 121.4(14) . . ? C5 C4 H4 116.2(14) . . ? C6 C5 C4 118.43(15) . . ? C6 C5 H5 116.1(13) . . ? C4 C5 H5 125.4(13) . . ? O4 C6 C5 122.60(14) . . ? O4 C6 C1 116.14(13) . . ? C5 C6 C1 121.25(15) . . ? O2 C7 O1 117.60(14) . . ? O2 C7 C1 122.20(14) . . ? O1 C7 C1 120.20(13) . . ? O4 C8 H8A 106.2(13) . . ? O4 C8 H8B 110.0(12) . . ? H8A C8 H8B 108.5(17) . . ? O4 C8 H8C 111.5(13) . . ? H8A C8 H8C 108.8(17) . . ? H8B C8 H8C 111.7(17) . . ? C7 O1 H1A 110.7(19) . . ? C2 O3 H3A 107(2) . . ? C6 O4 C8 119.56(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 O3 179.69(13) . . . . ? C7 C1 C2 O3 -0.8(2) . . . . ? C6 C1 C2 C3 -0.7(2) . . . . ? C7 C1 C2 C3 178.84(13) . . . . ? O3 C2 C3 C4 180.00(14) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 O4 -179.53(13) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C2 C1 C6 O4 -179.81(12) . . . . ? C7 C1 C6 O4 0.7(2) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C7 C1 C6 C5 -179.14(14) . . . . ? C2 C1 C7 O2 2.5(2) . . . . ? C6 C1 C7 O2 -177.97(14) . . . . ? C2 C1 C7 O1 -176.50(13) . . . . ? C6 C1 C7 O1 3.0(2) . . . . ? C5 C6 O4 C8 1.3(2) . . . . ? C1 C6 O4 C8 -178.56(13) . . . . ? 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 O3 H3A O2 0.97(4) 1.68(4) 2.5487(17) 147(3) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.331 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.055 # Attachment 'salicylic_acid.cif' data_salicylic_acid _database_code_depnum_ccdc_archive 'CCDC 871047' #TrackingRef 'salicylic_acid.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-hydroxobenzoic acid' ; _chemical_name_common 'salicylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O3' _chemical_formula_sum 'C7 H6 O3' _chemical_formula_weight 138.12 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 4.8894(3) _cell_length_b 11.2411(13) _cell_length_c 11.3347(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.919(7) _cell_angle_gamma 90.00 _cell_volume 622.63(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1388 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 2.91 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9658 _exptl_absorpt_correction_T_max 0.9988 _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 '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on -goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5347 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1413 _reflns_number_gt 1008 _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^)+(0.0000P)^2^+0.9891P] 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 1413 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.4955(5) 0.1924(2) 0.4172(2) 0.0240(6) Uani 1 1 d . . . C2 C 0.6443(5) 0.1681(2) 0.3158(2) 0.0265(6) Uani 1 1 d . . . C3 C 0.8410(5) 0.2492(2) 0.2802(2) 0.0305(6) Uani 1 1 d . . . H3 H 0.9434 0.2332 0.2122 0.037 Uiso 1 1 calc R . . C4 C 0.8872(5) 0.3523(3) 0.3429(3) 0.0324(7) Uani 1 1 d . . . H4 H 1.0212 0.4070 0.3176 0.039 Uiso 1 1 calc R . . C5 C 0.7406(6) 0.3776(3) 0.4432(3) 0.0332(7) Uani 1 1 d . . . H5 H 0.7735 0.4493 0.4858 0.040 Uiso 1 1 calc R . . C6 C 0.5471(5) 0.2977(2) 0.4799(2) 0.0292(6) Uani 1 1 d . . . H6 H 0.4477 0.3143 0.5486 0.035 Uiso 1 1 calc R . . C7 C 0.2856(5) 0.1087(2) 0.4551(2) 0.0240(6) Uani 1 1 d . . . O1 O 0.2330(3) 0.01498(16) 0.40107(16) 0.0273(4) Uani 1 1 d . . . O2 O 0.1606(4) 0.13864(17) 0.55148(16) 0.0291(5) Uani 1 1 d . . . H2 H 0.0440 0.0866 0.5670 0.044 Uiso 1 1 calc R . . O3 O 0.6072(4) 0.06838(18) 0.24958(17) 0.0342(5) Uani 1 1 d . . . H3A H 0.4796 0.0278 0.2767 0.051 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 C1 0.0212(13) 0.0250(14) 0.0260(13) 0.0044(11) 0.0017(10) 0.0002(10) C2 0.0251(14) 0.0258(15) 0.0288(14) 0.0041(11) 0.0038(11) -0.0012(11) C3 0.0279(15) 0.0334(16) 0.0307(15) 0.0049(12) 0.0077(11) -0.0019(12) C4 0.0264(15) 0.0313(16) 0.0396(16) 0.0096(13) 0.0026(12) -0.0071(12) C5 0.0311(16) 0.0246(15) 0.0439(17) 0.0030(13) -0.0005(13) -0.0032(12) C6 0.0269(15) 0.0294(16) 0.0317(15) 0.0016(12) 0.0051(11) -0.0002(11) C7 0.0204(13) 0.0250(14) 0.0269(13) 0.0028(11) 0.0040(10) 0.0014(10) O1 0.0262(10) 0.0247(10) 0.0314(11) -0.0010(8) 0.0104(8) -0.0046(8) O2 0.0289(11) 0.0275(11) 0.0316(10) -0.0023(8) 0.0120(8) -0.0060(8) O3 0.0362(12) 0.0324(12) 0.0349(11) -0.0020(9) 0.0147(9) -0.0070(9) _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 1.399(4) . ? C1 C2 1.408(3) . ? C1 C7 1.467(3) . ? C2 O3 1.358(3) . ? C2 C3 1.395(4) . ? C3 C4 1.374(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(4) . ? C4 H4 0.9500 . ? C5 C6 1.379(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.241(3) . ? C7 O2 1.314(3) . ? O2 H2 0.8400 . ? O3 H3A 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 119.3(2) . . ? C6 C1 C7 120.7(2) . . ? C2 C1 C7 120.0(2) . . ? O3 C2 C3 117.4(2) . . ? O3 C2 C1 123.3(2) . . ? C3 C2 C1 119.3(2) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O1 C7 O2 122.2(2) . . ? O1 C7 C1 122.4(2) . . ? O2 C7 C1 115.4(2) . . ? C7 O2 H2 109.5 . . ? C2 O3 H3A 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 O3 H3A O1 0.84 1.89 2.621(2) 144.6 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.295 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.061