#------------------------------------------------------------------------------ #$Date: 2021-12-17 04:59:22 +0200 (Fri, 17 Dec 2021) $ #$Revision: 271493 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243954.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2243954 loop_ _publ_author_name 'Halz, Jan Henrik' 'Hentsch, Andreas' 'Wagner, Christoph' 'Merzweiler, Kurt' _publ_section_title ; Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid ; _journal_coeditor_code WM5628 _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first ; ; _journal_paper_doi 10.1107/S2056989021013050 _journal_volume 78 _journal_year 2022 _chemical_formula_iupac 'C13 H13 N O4' _chemical_formula_moiety 'C13 H13 N O4' _chemical_formula_sum 'C13 H13 N O4' _chemical_formula_weight 247.24 _chemical_name_common ; 3-[(2-Carboxyphenylamino)methylidene]pentane-2,4-dione ; _chemical_name_systematic ; 2-[(2-Acetyl-3-oxobut-1-en-1-yl)amino]benzoic acid ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 92.836(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.6287(5) _cell_length_b 12.3740(4) _cell_length_c 17.5419(7) _cell_measurement_reflns_used 22415 _cell_measurement_temperature 170 _cell_measurement_theta_max 29.59 _cell_measurement_theta_min 2.53 _cell_volume 2304.28(16) _computing_cell_refinement ; X-Area (Stoe, 2016) ; _computing_data_collection ; X-Area (Stoe, 2016) ; _computing_data_reduction ; X-Area (Stoe, 2016) ; _computing_molecular_graphics ; DIAMOND (Brandenburg et al., 2019) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 170 _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device '2-circle diffractometer' _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_unetI/netI 0.0300 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 5925 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.997 _diffrn_reflns_theta_min 2.528 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.318 _exptl_crystal_size_mid 0.226 _exptl_crystal_size_min 0.141 _refine_diff_density_max 0.198 _refine_diff_density_min -0.253 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2242 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0463 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+1.8130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.1268 _reflns_number_gt 2041 _reflns_number_total 2242 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5628sup1.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2243954 _shelx_estimated_absorpt_t_min 0.967 _shelx_estimated_absorpt_t_max 0.985 _shelx_hkl_file ; -9 -3 19 4.41 1.86 -9 -1 18 2.81 1.50 -9 1 18 -1.47 1.46 -9 3 19 3.89 1.28 -8 -6 17 4.72 1.92 -8 -6 18 7.18 2.01 -8 -4 15 30.36 1.60 -8 -2 13 31.24 1.27 -8 0 13 1.56 0.96 -8 6 17 2.93 0.77 -7 -7 14 53.76 1.84 -7 -7 15 50.70 1.92 -7 -5 12 14.19 1.39 -7 -1 10 -0.67 0.84 -7 1 10 1.18 0.69 -7 5 12 9.03 0.57 -6 -10 16 2.17 1.59 -6 -10 17 5.27 2.24 -6 -8 13 9.52 1.65 -6 -6 10 8.92 1.21 -6 -4 9 355.19 2.11 -6 -2 8 129.24 1.28 -6 2 8 130.67 0.92 -5 -11 15 37.54 2.19 -5 -11 16 29.79 2.37 -5 -9 11 35.79 1.30 -5 -7 9 12.92 1.29 -4 -12 15 20.62 2.24 -4 -10 11 6.90 1.52 -4 -8 8 341.19 2.30 -4 -4 5 1285.31 2.99 -4 10 10 27.63 0.67 -3 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415.67 2.04 0 -6 -14 -0.67 1.09 0 8 5 356.43 1.63 0 12 5 53.99 1.20 1 3 3 2555.93 2.89 1 7 5 12.81 0.81 2 14 5 14.23 1.46 3 -7 -20 1.22 1.54 3 -7 -19 3.62 1.45 3 15 5 6.51 1.72 4 -6 -11 22.28 0.69 4 4 4 281.85 1.47 4 14 5 47.21 1.93 5 3 3 994.08 2.67 5 7 5 100.55 1.51 5 13 5 83.27 1.99 6 -6 -12 50.44 0.67 6 0 0 127.40 1.05 6 2 2 169.72 1.31 6 8 5 550.62 2.89 6 10 5 515.47 3.08 6 12 5 40.80 1.87 7 11 5 68.37 1.65 8 0 -1 -0.01 0.71 8 2 1 227.94 1.65 8 8 4 32.01 1.60 8 12 4 13.38 2.08 9 3 1 29.58 1.19 9 7 3 44.75 1.67 10 -2 -6 116.70 1.06 10 4 1 3.24 1.24 10 6 2 5.18 1.45 10 10 3 6.16 1.94 11 1 -3 61.71 1.41 11 3 -1 -1.70 1.21 11 9 2 -3.86 1.93 12 2 -3 4.53 1.22 12 6 0 2.65 1.70 13 -1 -10 -1.34 1.09 13 5 -2 38.61 1.93 13 7 -1 -0.34 2.01 -10 4 -13 55.16 1.90 -10 4 -12 35.86 1.69 -10 6 -9 4.96 1.40 -10 8 -8 25.75 1.18 -10 10 -7 12.01 1.22 -9 1 -18 6.82 2.00 -9 1 -17 25.95 1.99 -9 1 -16 40.97 2.10 -9 1 -15 35.20 1.93 -9 1 -14 83.87 2.01 -9 3 -9 143.90 1.80 -9 5 -7 107.70 1.37 -8 0 -13 -2.83 1.33 -8 0 -12 27.22 1.50 -8 2 -8 9.17 1.12 -7 -1 -11 6.40 1.29 -7 1 -7 49.32 1.17 -7 3 -4 107.54 1.15 -6 -2 -11 186.31 1.89 -6 0 -6 3.98 0.83 -5 -3 -11 13.91 1.29 -5 -1 -6 4.57 0.82 -5 1 -3 119.55 1.01 -5 3 -1 93.52 0.66 -4 -4 -12 1289.69 3.96 -4 0 -3 1.72 0.55 -3 -5 -15 289.16 2.18 -3 -5 -14 30.60 1.42 -3 -3 -7 13.35 0.85 -3 13 3 76.89 1.11 -2 -6 -21 34.95 2.21 -2 -6 -20 194.35 2.56 -2 -6 -19 69.59 1.95 -2 -6 -18 21.09 1.64 -2 -4 -8 24.02 0.88 -2 -2 -4 528.53 1.55 -2 10 4 32.96 0.83 -1 -5 -10 275.04 1.69 -1 -3 -5 423.75 1.37 -1 7 4 1.41 0.64 0 -6 -13 41.97 1.19 0 10 5 120.61 1.26 1 -7 -20 36.31 1.92 1 -7 -19 5.53 1.65 1 -5 -8 -0.73 0.60 1 5 4 682.03 1.89 1 9 5 0.20 0.88 1 11 5 54.19 1.37 1 13 5 4.84 1.19 2 -6 -11 9.45 0.74 2 8 5 145.71 1.40 2 16 4 13.20 1.76 3 -7 -21 138.36 2.06 3 -7 -18 32.67 1.28 3 -7 -17 130.35 1.57 3 -7 -16 84.39 1.43 3 3 3 2281.34 3.36 3 7 5 10.69 0.97 3 13 5 6.48 1.41 4 -2 -2 425.36 0.79 4 8 5 562.03 2.61 4 12 5 66.45 1.75 4 16 4 5.70 2.03 5 -7 -20 62.00 1.58 5 -7 -19 8.12 1.24 5 -7 -18 59.35 1.33 5 -7 -17 -0.59 1.02 5 5 4 190.70 1.55 5 9 5 573.92 2.93 5 11 5 63.53 1.68 5 15 4 17.45 2.06 6 4 3 272.96 1.76 6 6 4 10.12 1.16 6 14 4 19.68 2.09 7 -3 -5 121.51 0.63 7 3 2 381.92 1.99 7 5 3 391.69 2.27 7 7 4 57.15 1.43 7 13 4 146.58 2.56 8 -2 -4 17.06 0.58 8 4 2 126.16 1.57 8 6 3 23.66 1.35 8 10 4 84.99 1.73 9 -3 -7 313.12 1.16 9 1 -1 79.01 1.17 9 5 2 -2.85 1.13 9 9 3 14.95 1.67 9 11 3 246.95 3.03 9 13 3 17.01 2.18 10 2 -1 5.21 1.05 10 8 2 49.84 1.88 10 12 2 41.58 2.54 11 -1 -6 47.50 0.96 11 5 0 0.91 1.44 11 7 1 8.06 1.58 11 9 1 1.02 1.74 12 -2 -10 0.15 0.79 12 4 -2 2.77 1.45 12 6 -1 9.54 1.63 12 8 0 48.76 2.24 13 3 -4 3.08 1.44 13 5 -3 5.50 1.59 13 7 -2 6.97 1.93 -10 2 -16 87.27 2.42 -10 2 -15 64.58 2.02 -10 4 -11 159.86 2.02 -10 8 -7 35.66 1.21 -9 1 -13 8.27 1.61 -9 1 -12 17.34 1.53 -9 7 -5 131.07 1.28 -8 0 -11 -0.18 1.33 -8 2 -7 158.01 1.56 -8 4 -5 175.61 1.35 -7 -1 -10 178.42 1.89 -7 1 -6 13.26 0.94 -6 -2 -10 277.80 2.09 -5 -3 -10 60.50 1.41 -4 -4 -11 2123.31 4.81 -4 -2 -6 558.91 2.04 -3 -5 -13 138.11 1.55 -3 -5 -12 6.40 1.21 -3 15 2 87.89 1.46 -2 -6 -22 71.97 2.44 -2 -6 -17 154.49 2.02 -2 -6 -16 427.37 2.80 -2 -6 -15 348.57 2.46 -2 14 3 5.32 1.12 -2 16 2 0.46 1.29 -1 -5 -9 1.30 0.81 -1 13 4 174.92 1.59 -1 15 3 3.26 1.30 0 -6 -12 725.05 2.65 0 -4 -6 194.39 1.05 0 6 4 3388.82 3.92 0 14 4 1.86 1.13 0 16 3 1.03 1.37 1 -7 -21 28.45 1.81 1 -7 -18 72.03 1.61 1 -7 -17 641.95 3.05 1 -7 -16 402.00 2.42 1 15 4 43.61 1.58 2 -6 -10 361.88 1.62 2 10 5 8.83 1.09 2 12 5 57.30 1.39 3 -7 -15 37.99 1.03 3 5 4 238.53 1.46 3 9 5 83.76 1.41 3 11 5 208.06 1.99 3 15 4 76.34 2.03 4 2 2 1113.65 2.38 4 10 5 29.32 1.30 4 14 4 58.58 1.87 5 -7 -16 14.40 0.92 5 1 1 4.13 0.65 6 8 4 8.59 1.31 6 12 4 6.62 1.67 7 1 0 190.94 1.33 7 9 4 3.94 1.07 7 11 4 0.80 1.53 8 8 3 10.97 1.47 8 12 3 66.76 2.28 9 7 2 107.36 1.90 9 13 2 19.91 2.38 10 4 0 15.86 1.28 10 6 1 47.71 1.64 10 10 2 -0.79 1.36 11 3 -2 26.17 1.32 11 7 0 0.95 1.53 12 2 -4 11.01 1.25 12 8 -1 3.29 1.77 13 3 -5 13.12 1.49 -11 5 -13 188.23 2.50 -11 7 -11 30.82 1.61 -10 2 -14 4.51 1.76 -10 2 -13 2.13 1.64 -10 4 -10 252.58 2.22 -10 6 -8 12.15 1.11 -9 1 -11 7.30 1.40 -9 3 -8 4.84 1.07 -9 5 -6 70.36 1.14 -8 -2 -19 63.23 2.49 -8 -2 -18 32.46 2.20 -8 -2 -17 -2.22 1.89 -8 -2 -16 127.16 2.27 -8 0 -10 714.38 3.17 -7 -3 -19 14.67 2.14 -7 -3 -18 36.28 2.10 -7 -3 -17 10.25 1.85 -7 -3 -16 88.10 2.09 -7 -3 -15 2.26 1.52 -7 -1 -9 167.39 1.75 -6 -4 -20 16.19 2.20 -6 -4 -19 30.51 2.13 -6 -4 -18 75.46 2.21 -6 -4 -17 64.26 2.03 -6 -4 -16 9.13 1.69 -6 -2 -9 3725.17 6.19 -6 2 -3 372.76 1.48 -5 -5 -20 6.38 2.11 -5 -5 -19 62.09 2.18 -5 -5 -18 11.63 1.69 -5 -3 -9 8.34 1.16 -4 -4 -10 1712.61 4.20 -3 -5 -11 1508.94 4.02 -3 -3 -6 64.55 0.98 -3 -1 -3 449.03 1.36 -2 -6 -14 1320.23 4.12 -2 -6 -13 228.33 1.96 -2 -4 -7 368.03 1.68 -2 0 -1 -0.10 0.29 -1 -7 -21 15.29 1.93 -1 -7 -20 89.62 2.14 -1 -7 -19 8.06 1.66 -1 -7 -18 98.27 1.92 -1 9 4 66.87 0.91 -1 11 4 133.75 1.26 0 -6 -11 202.81 1.54 0 4 3 40.40 0.54 1 -7 -15 345.73 2.15 2 2 2 1055.91 1.89 2 6 4 1004.19 2.59 2 14 4 10.47 1.43 2 16 3 4.71 1.72 3 -7 -14 35.61 0.97 4 4 3 945.80 2.55 4 6 4 105.56 1.28 4 16 3 -2.97 1.92 5 7 4 21.54 1.19 5 11 4 2.55 1.32 5 13 4 13.81 1.60 5 15 3 3.01 1.96 6 10 4 63.37 1.73 6 14 3 62.17 2.28 7 7 3 0.73 1.24 7 13 3 241.91 2.94 8 2 0 131.59 1.37 8 6 2 215.16 2.03 8 10 3 152.22 2.04 9 -1 -4 -0.22 0.63 9 3 0 70.18 1.29 9 5 1 22.35 1.34 9 9 2 -1.10 1.63 9 11 2 111.90 2.41 10 2 -2 2.51 1.02 10 8 1 6.67 1.65 10 10 1 0.58 1.84 10 12 1 89.74 2.77 11 1 -4 4.99 1.03 11 5 -1 109.56 1.92 11 9 0 9.70 1.94 11 11 0 2.40 2.21 12 0 -7 -1.81 0.93 12 4 -3 3.74 1.42 12 6 -2 0.82 1.69 13 5 -4 19.06 1.83 13 7 -3 14.19 2.05 -5 -5 -17 -0.33 1.25 -5 -1 -5 1092.84 2.67 5 9 4 304.27 2.10 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 74507 _shelx_res_file ; i2t2025.res created by SHELXL-2014/7 TITL i2t2025_a.res in C2/c REM Old TITL REM SHELXT solution in C2/c REM R1 0.112, Rweak 0.006, Alpha 0.052, Orientation as input REM Formula found by SHELXT: C13 N O4 CELL 0.71073 10.6287 12.374 17.5419 90 92.836 90 ZERR 8 0.0005 0.0004 0.0007 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 104 104 8 32 L.S. 10 PLAN 20 SIZE 0.141 0.226 0.318 BOND $H list 4 fmap 2 53 acta OMIT -6 52 OMIT -6 8 12 REM REM REM WGHT 0.067300 1.765100 FVAR 0.54193 O1 4 0.459602 0.159969 0.479329 11.00000 0.04090 0.03724 = 0.02674 -0.00385 -0.01756 0.00431 N 3 0.369839 0.356338 0.495439 11.00000 0.02459 0.02909 = 0.01725 -0.00101 -0.00705 -0.00044 AFIX 43 H 2 0.416441 0.307307 0.517133 11.00000 -1.20000 AFIX 0 O4 4 0.534527 0.305198 0.614071 11.00000 0.04018 0.03166 = 0.02837 -0.00244 -0.01468 0.00334 O3 4 0.614283 0.446763 0.679132 11.00000 0.03846 0.03410 = 0.03292 -0.00023 -0.02208 -0.00011 AFIX 147 H3 2 0.659014 0.400256 0.699866 11.00000 -1.50000 AFIX 0 O2 4 0.278588 0.162110 0.264107 11.00000 0.04064 0.04043 = 0.02483 -0.00823 -0.01508 0.00311 C7 1 0.354328 0.453983 0.535288 11.00000 0.02255 0.02957 = 0.01708 0.00033 -0.00258 -0.00258 C8 1 0.433103 0.477854 0.600389 11.00000 0.02418 0.02984 = 0.01558 0.00160 -0.00316 -0.00353 C13 1 0.530737 0.400130 0.630584 11.00000 0.02829 0.03146 = 0.01454 0.00161 -0.00542 -0.00337 C6 1 0.317389 0.334536 0.426467 11.00000 0.02237 0.03296 = 0.01764 0.00267 -0.00558 -0.00292 AFIX 43 H6 2 0.263644 0.386939 0.405197 11.00000 -1.20000 AFIX 0 C10 1 0.328140 0.650498 0.613131 11.00000 0.03292 0.03103 = 0.02688 -0.00327 0.00089 -0.00021 AFIX 43 H10 2 0.320522 0.716137 0.638312 11.00000 -1.20000 AFIX 0 C12 1 0.262378 0.529317 0.511801 11.00000 0.02753 0.03720 = 0.02340 0.00038 -0.00837 0.00139 AFIX 43 H12 2 0.208993 0.514113 0.469556 11.00000 -1.20000 AFIX 0 C9 1 0.417998 0.576061 0.637827 11.00000 0.02981 0.03451 = 0.01838 -0.00093 -0.00294 -0.00370 AFIX 43 H9 2 0.469879 0.591877 0.680620 11.00000 -1.20000 AFIX 0 C4 1 0.264852 0.238120 0.308934 11.00000 0.02419 0.03374 = 0.01904 0.00062 -0.00582 -0.00576 C3 1 0.333931 0.242800 0.383040 11.00000 0.02247 0.03249 = 0.01797 -0.00054 -0.00596 -0.00406 C2 1 0.417268 0.155561 0.412376 11.00000 0.02655 0.03503 = 0.02305 -0.00094 -0.00737 -0.00330 C11 1 0.249269 0.625625 0.549984 11.00000 0.02962 0.03424 = 0.03061 0.00225 -0.00300 0.00516 AFIX 43 H11 2 0.187191 0.674373 0.533394 11.00000 -1.20000 AFIX 0 C5 1 0.173662 0.327330 0.285329 11.00000 0.03047 0.04193 = 0.02233 -0.00097 -0.01103 0.00044 AFIX 137 H5A 2 0.218947 0.393888 0.280390 11.00000 -1.50000 H5B 2 0.112410 0.335436 0.323346 11.00000 -1.50000 H5C 2 0.131775 0.309264 0.237276 11.00000 -1.50000 AFIX 0 C1 1 0.454924 0.061911 0.364086 11.00000 0.04168 0.04596 = 0.03148 -0.00765 -0.01106 0.01186 AFIX 137 H1A 2 0.500086 0.009911 0.395482 11.00000 -1.50000 H1B 2 0.507873 0.087164 0.325043 11.00000 -1.50000 H1C 2 0.380890 0.028777 0.340857 11.00000 -1.50000 AFIX 0 HKLF 4 REM i2t2025_a.res in C2/c REM R1 = 0.0463 for 2041 Fo > 4sig(Fo) and 0.0507 for all 2242 data REM 166 parameters refined using 0 restraints END WGHT 0.0677 1.8136 REM Highest difference peak 0.198, deepest hole -0.253, 1-sigma level 0.052 Q1 1 0.2838 0.4198 0.3942 11.00000 0.05 0.20 Q2 1 0.3025 0.6304 0.5835 11.00000 0.05 0.18 Q3 1 0.3623 0.5871 0.6367 11.00000 0.05 0.17 Q4 1 0.2704 0.2251 0.3598 11.00000 0.05 0.16 Q5 1 0.2031 0.7182 0.5063 11.00000 0.05 0.16 Q6 1 0.4152 0.4646 0.5658 11.00000 0.05 0.15 Q7 1 0.3455 0.7067 0.5415 11.00000 0.05 0.15 Q8 1 0.4633 0.4419 0.6166 11.00000 0.05 0.15 Q9 1 0.7036 0.4988 0.6433 11.00000 0.05 0.14 Q10 1 0.3200 0.4938 0.5158 11.00000 0.05 0.14 Q11 1 0.4460 0.5250 0.5048 11.00000 0.05 0.14 Q12 1 0.4763 -0.0187 0.4068 11.00000 0.05 0.13 Q13 1 0.6466 0.4751 0.6166 11.00000 0.05 0.13 Q14 1 0.3923 0.2219 0.3848 11.00000 0.05 0.13 Q15 1 0.0945 0.3740 0.3244 11.00000 0.05 0.13 Q16 1 0.2463 0.1470 0.3007 11.00000 0.05 0.13 Q17 1 0.5000 0.6612 0.7500 10.50000 0.05 0.13 Q18 1 0.3598 0.3445 0.4610 11.00000 0.05 0.13 Q19 1 0.3522 0.2992 0.3968 11.00000 0.05 0.13 Q20 1 0.3661 0.2450 0.3772 11.00000 0.05 0.13 ; _shelx_res_checksum 16884 loop_ _space_group_symop_operation_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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.45960(11) 0.15997(10) 0.47933(6) 0.0356(3) Uani d 1 . . O O2 0.27859(11) 0.16211(10) 0.26411(6) 0.0358(3) Uani d 1 . . O O3 0.61428(11) 0.44676(10) 0.67913(7) 0.0359(3) Uani d 1 . . H H13 0.6590 0.4003 0.6999 0.054 Uiso calc 1 . . O O4 0.53453(11) 0.30520(10) 0.61407(6) 0.0339(3) Uani d 1 . . N N 0.36984(11) 0.35634(11) 0.49544(7) 0.0239(3) Uani d 1 . . H H8 0.4164 0.3073 0.5171 0.029 Uiso calc 1 . . C C1 0.45492(18) 0.06191(16) 0.36409(10) 0.0401(4) Uani d 1 . . H H1 0.5001 0.0099 0.3955 0.060 Uiso calc 1 . . H H2 0.5079 0.0872 0.3250 0.060 Uiso calc 1 . . H H3 0.3809 0.0288 0.3409 0.060 Uiso calc 1 . . C C2 0.41727(14) 0.15556(13) 0.41238(9) 0.0285(4) Uani d 1 . . C C3 0.33393(13) 0.24280(13) 0.38304(8) 0.0245(3) Uani d 1 . . C C4 0.26485(13) 0.23812(13) 0.30893(8) 0.0259(3) Uani d 1 . . C C5 0.17366(15) 0.32733(15) 0.28533(9) 0.0320(4) Uani d 1 . . H H4 0.1318 0.3093 0.2373 0.048 Uiso calc 1 . . H H5 0.2189 0.3939 0.2804 0.048 Uiso calc 1 . . H H6 0.1124 0.3354 0.3233 0.048 Uiso calc 1 . . C C6 0.31739(13) 0.33454(13) 0.42647(8) 0.0245(3) Uani d 1 . . H H7 0.2636 0.3869 0.4052 0.029 Uiso calc 1 . . C C7 0.35433(13) 0.45398(13) 0.53529(8) 0.0232(3) Uani d 1 . . C C8 0.43310(13) 0.47785(13) 0.60039(7) 0.0233(3) Uani d 1 . . C C9 0.41800(14) 0.57606(13) 0.63783(8) 0.0277(4) Uani d 1 . . H H9 0.4699 0.5919 0.6806 0.033 Uiso calc 1 . . C C10 0.32814(15) 0.65050(14) 0.61313(9) 0.0303(4) Uani d 1 . . H H10 0.3205 0.7161 0.6383 0.036 Uiso calc 1 . . C C11 0.24927(15) 0.62563(14) 0.54998(9) 0.0316(4) Uani d 1 . . H H11 0.1872 0.6744 0.5334 0.038 Uiso calc 1 . . C C12 0.26238(14) 0.52931(14) 0.51180(8) 0.0297(4) Uani d 1 . . H H12 0.2090 0.5141 0.4696 0.036 Uiso calc 1 . . C C13 0.53074(14) 0.40013(13) 0.63058(8) 0.0250(3) Uani d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0409(7) 0.0372(7) 0.0267(6) 0.0043(5) -0.0176(5) -0.0039(5) O2 0.0406(7) 0.0404(7) 0.0248(6) 0.0031(5) -0.0151(5) -0.0082(5) O3 0.0385(6) 0.0341(7) 0.0329(6) -0.0001(5) -0.0221(5) -0.0002(5) O4 0.0402(6) 0.0316(7) 0.0284(6) 0.0033(5) -0.0147(5) -0.0024(5) N 0.0246(6) 0.0291(7) 0.0173(6) -0.0004(5) -0.0070(5) -0.0010(5) C1 0.0417(9) 0.0459(11) 0.0315(9) 0.0119(8) -0.0111(7) -0.0077(8) C2 0.0265(7) 0.0350(9) 0.0230(7) -0.0033(6) -0.0074(6) -0.0009(6) C3 0.0225(7) 0.0325(8) 0.0180(7) -0.0041(6) -0.0060(5) -0.0005(6) C4 0.0242(7) 0.0337(9) 0.0190(7) -0.0058(6) -0.0058(5) 0.0006(6) C5 0.0305(8) 0.0419(10) 0.0223(7) 0.0004(7) -0.0110(6) -0.0010(7) C6 0.0224(7) 0.0329(8) 0.0176(7) -0.0029(6) -0.0056(5) 0.0027(6) C7 0.0225(7) 0.0296(8) 0.0171(6) -0.0026(6) -0.0026(5) 0.0003(6) C8 0.0242(7) 0.0298(8) 0.0156(6) -0.0035(6) -0.0032(5) 0.0016(6) C9 0.0298(8) 0.0345(9) 0.0184(7) -0.0037(6) -0.0029(6) -0.0009(6) C10 0.0329(8) 0.0310(8) 0.0269(8) -0.0002(6) 0.0009(6) -0.0033(6) C11 0.0296(8) 0.0342(9) 0.0306(8) 0.0052(7) -0.0030(6) 0.0023(7) C12 0.0275(7) 0.0372(9) 0.0234(7) 0.0014(6) -0.0084(6) 0.0004(6) C13 0.0283(7) 0.0314(9) 0.0145(6) -0.0034(6) -0.0054(5) 0.0016(6) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C13 O3 H13 . . 109.5 ? C6 N H8 . . 117.7 ? C6 N C7 . . 124.68(13) ? C7 N H8 . . 117.7 ? H1 C1 H2 . . 109.5 ? H1 C1 H3 . . 109.5 ? H2 C1 H3 . . 109.5 ? C2 C1 H1 . . 109.5 ? C2 C1 H2 . . 109.5 ? C2 C1 H3 . . 109.5 ? O1 C2 C1 . . 118.34(14) ? O1 C2 C3 . . 118.90(14) ? C3 C2 C1 . . 122.75(13) ? C4 C3 C2 . . 123.26(14) ? C6 C3 C2 . . 119.98(12) ? C6 C3 C4 . . 116.76(13) ? O2 C4 C3 . . 121.63(14) ? O2 C4 C5 . . 118.30(13) ? C3 C4 C5 . . 120.07(14) ? C4 C5 H4 . . 109.5 ? C4 C5 H5 . . 109.5 ? C4 C5 H6 . . 109.5 ? H4 C5 H5 . . 109.5 ? H4 C5 H6 . . 109.5 ? H5 C5 H6 . . 109.5 ? N C6 C3 . . 127.34(14) ? N C6 H7 . . 116.3 ? C3 C6 H7 . . 116.3 ? N C7 C8 . . 120.04(13) ? C12 C7 N . . 121.51(13) ? C12 C7 C8 . . 118.45(14) ? C7 C8 C13 . . 121.72(14) ? C9 C8 C7 . . 119.03(14) ? C9 C8 C13 . . 119.25(12) ? C8 C9 H9 . . 119.1 ? C10 C9 C8 . . 121.83(14) ? C10 C9 H9 . . 119.1 ? C9 C10 H10 . . 120.6 ? C9 C10 C11 . . 118.86(15) ? C11 C10 H10 . . 120.6 ? C10 C11 H11 . . 119.8 ? C12 C11 C10 . . 120.49(15) ? C12 C11 H11 . . 119.8 ? C7 C12 H12 . . 119.3 ? C11 C12 C7 . . 121.31(14) ? C11 C12 H12 . . 119.3 ? O3 C13 C8 . . 112.20(13) ? O4 C13 O3 . . 122.99(14) ? O4 C13 C8 . . 124.81(13) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.2380(18) y O2 C4 . 1.239(2) y O3 H13 . 0.8200 ? O3 C13 . 1.3312(17) ? O4 C13 . 1.211(2) ? N H8 . 0.8600 ? N C6 . 1.3344(18) y N C7 . 1.410(2) ? C1 H1 . 0.9600 ? C1 H2 . 0.9600 ? C1 H3 . 0.9600 ? C1 C2 . 1.501(2) y C2 C3 . 1.473(2) y C3 C4 . 1.4621(18) y C3 C6 . 1.383(2) y C4 C5 . 1.513(2) y C5 H4 . 0.9600 ? C5 H5 . 0.9600 ? C5 H6 . 0.9600 ? C6 H7 . 0.9300 ? C7 C8 . 1.4135(19) ? C7 C12 . 1.398(2) ? C8 C9 . 1.394(2) ? C8 C13 . 1.493(2) ? C9 H9 . 0.9300 ? C9 C10 . 1.381(2) ? C10 H10 . 0.9300 ? C10 C11 . 1.390(2) ? C11 H11 . 0.9300 ? C11 C12 . 1.378(2) ? C12 H12 . 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O3 H13 O2 8_556 0.82 1.83 2.6132(15) 160.1 N H8 O1 . 0.86 2.00 2.6308(18) 129.2 N H8 O4 . 0.86 2.06 2.7266(16) 133.4 C5 H6 O4 7_556 0.96 2.62 3.330(2) 131.4 C11 H11 O1 3_455 0.93 2.56 3.2891(19) 135.5 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -171.05(14) ? O1 C2 C3 C6 . . . . 8.5(2) ? N C7 C8 C9 . . . . 178.50(13) ? N C7 C8 C13 . . . . -2.3(2) ? N C7 C12 C11 . . . . -178.64(14) ? C1 C2 C3 C4 . . . . 9.9(2) ? C1 C2 C3 C6 . . . . -170.53(15) ? C2 C3 C4 O2 . . . . -4.4(2) ? C2 C3 C4 C5 . . . . 175.49(14) ? C2 C3 C6 N . . . . 0.1(2) ? C4 C3 C6 N . . . . 179.70(14) ? C6 N C7 C8 . . . . -167.19(14) y C6 N C7 C12 . . . . 12.5(2) ? C6 C3 C4 O2 . . . . 176.05(14) y C6 C3 C4 C5 . . . . -4.1(2) ? C7 N C6 C3 . . . . 176.56(14) ? C7 C8 C9 C10 . . . . 0.1(2) ? C7 C8 C13 O3 . . . . 164.41(13) ? C7 C8 C13 O4 . . . . -16.2(2) ? C8 C7 C12 C11 . . . . 1.1(2) ? C8 C9 C10 C11 . . . . 1.2(2) ? C9 C8 C13 O3 . . . . -16.39(19) ? C9 C8 C13 O4 . . . . 163.00(15) ? C9 C10 C11 C12 . . . . -1.3(2) ? C10 C11 C12 C7 . . . . 0.2(2) ? C12 C7 C8 C9 . . . . -1.2(2) ? C12 C7 C8 C13 . . . . 178.00(13) ? C13 C8 C9 C10 . . . . -179.13(14) ? _cod_database_fobs_code 2243954