#------------------------------------------------------------------------------ #$Date: 2014-10-16 00:49:47 +0300 (Thu, 16 Oct 2014) $ #$Revision: 125434 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/00/2240074.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_2240074 loop_ _publ_author_name 'G\"orbitz, Carl Henrik' _publ_section_title ; Redetermined structure of \b-DL-methionine at 105K: an example of the importance of freely refining the positions of the amino-group H atoms ; _journal_coeditor_code HB7289 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 341 _journal_page_last 343 _journal_paper_doi 10.1107/S1600536814022223 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C5 H11 N O2 S' _chemical_formula_moiety 'C5 H11 N O2 S' _chemical_formula_sum 'C5 H11 N O2 S' _chemical_formula_weight 149.21 _chemical_name_common DL-methionine _chemical_name_systematic ; 2-Amino-4-(methylsulfanyl)butanoic acid ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _symmetry_space_group_name_Hall '-I 2ya' _symmetry_space_group_name_H-M 'I 1 2/a 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _cell_angle_alpha 90 _cell_angle_beta 106.250(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.877(2) _cell_length_b 4.6915(10) _cell_length_c 32.603(6) _cell_measurement_reflns_used 1012 _cell_measurement_temperature 105(2) _cell_measurement_theta_max 26.1 _cell_measurement_theta_min 2.6 _cell_volume 1450.4(5) _computing_cell_refinement ; SAINT-NT (Bruker, 1999) ; _computing_data_collection ; SMART-NT (Bruker, 1999) ; _computing_data_reduction ; SAINT-NT (Bruker, 1999) ; _computing_molecular_graphics ; SHELXTL (Sheldrick, 2008) ; _computing_publication_material ; SHELXL2013 (Sheldrick, 2008) ; _computing_structure_refinement ; SHELXL2013 (Sheldrick, 2008) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 105(2) _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method 'Sets of exposures each taken over 0.5\% \w rotation' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 6469 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.295 _diffrn_reflns_theta_min 2.603 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 1998) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.367 _exptl_crystal_description block _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.349 _refine_diff_density_min -0.229 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1436 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.259 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0377 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+2.4782P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0913 _refine_ls_wR_factor_ref 0.0918 _reflns_number_gt 1373 _reflns_number_total 1436 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hb7289sup1.cif _[local]_cod_data_source_block I _cod_database_code 2240074 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_hkl_file ; 2 0 0 2678.06 78.13 4 0 0 9025.44 261.54 6 0 0 261.70 10.33 8 0 0 6.90 3.17 10 0 0 908.49 19.68 1 1 015824.95 235.31 3 1 0 373.35 11.44 5 1 0 402.39 8.01 7 1 0 436.70 6.63 9 1 0 1673.31 24.37 11 1 0 742.00 20.52 0 2 018650.03 391.06 2 2 0 1624.07 46.77 4 2 0 6080.99 90.43 6 2 0 25.38 3.97 8 2 0 48.04 2.78 10 2 0 101.73 3.50 1 3 0 40.99 2.85 3 3 0 247.79 3.94 5 3 0 5.37 1.47 7 3 0 72.97 3.16 9 3 0 165.73 4.97 0 4 0 1406.97 56.84 2 4 0 919.48 12.34 4 4 0 39.34 4.28 6 4 0 155.88 3.91 8 4 0 5.29 3.26 1 5 0 504.36 7.83 3 5 0 166.39 7.46 5 5 0 377.36 8.03 -10 1 1 660.55 8.83 -8 1 1 605.37 7.87 -6 1 1 21.87 3.46 -4 1 1 746.12 13.43 -2 1 1 5394.64 82.51 0 1 1 1422.30 31.04 2 1 1 1564.08 30.23 4 1 1 5017.35 85.62 6 1 1 234.78 8.78 8 1 1 76.61 2.86 10 1 1 27.13 2.35 -11 2 1 97.10 4.06 -9 2 1 1617.13 21.34 -7 2 1 691.42 9.05 -5 2 1 591.68 9.70 -3 2 1 1549.71 23.50 -1 2 1 72.25 3.05 1 2 1 2280.59 34.24 3 2 1 6111.83 90.76 5 2 1 52.61 3.89 7 2 1 1404.10 18.41 9 2 1 247.92 5.08 -10 3 1 446.50 12.04 -8 3 1 203.63 5.11 -6 3 1 561.12 9.48 -4 3 1 301.90 4.74 -2 3 1 3290.56 49.35 0 3 1 1359.16 24.37 2 3 1 1475.73 26.43 4 3 1 2337.69 23.70 6 3 1 14.52 3.18 8 3 1 836.86 13.25 -7 4 1 78.17 3.94 -5 4 1 732.91 10.35 -3 4 1 743.14 9.53 -1 4 1 434.62 6.63 1 4 1 114.56 4.44 3 4 1 268.64 4.86 5 4 1 381.83 6.27 7 4 1 1309.28 30.71 -4 5 1 277.20 6.75 -2 5 1 100.34 3.45 0 5 1 39.34 2.70 2 5 1 424.09 6.90 4 5 1 17.88 3.58 -10 0 2 986.05 36.59 -8 0 2 134.30 5.47 -6 0 210625.05 308.02 -4 0 2 3312.31 70.10 -2 0 2 3481.44 73.93 2 0 2 1644.66 48.24 4 0 2 8435.45 244.50 6 0 2 2106.75 62.69 8 0 2 116.45 6.06 10 0 2 72.76 5.38 -11 1 2 29.70 6.90 -9 1 2 11.10 2.14 -7 1 2 189.20 5.08 -5 1 2 56.26 5.22 -1 1 2 30.00 3.13 1 1 2 66.95 2.91 3 1 2 5357.96 112.36 5 1 2 3802.43 108.27 7 1 2 1504.55 20.42 9 1 2 769.33 9.88 11 1 2 114.22 5.84 -10 2 2 106.28 3.46 -8 2 2 198.20 4.36 -6 2 2 1361.72 16.44 -4 2 2 159.95 5.15 -2 2 2 2635.83 54.79 2 2 2 995.43 25.46 4 2 2 178.20 5.53 6 2 2 36.18 1.98 8 2 2 23.33 2.27 10 2 2 4.68 2.44 -9 3 2 441.71 17.49 -7 3 2 91.40 3.34 -5 3 2 39.92 2.23 -3 3 2 298.42 4.45 -1 3 2 404.17 13.46 1 3 2 833.73 27.58 3 3 2 105.20 4.12 5 3 2 1.48 1.59 7 3 2 12.36 2.24 9 3 2 143.12 4.74 -8 4 2 72.81 4.05 -6 4 2 190.01 7.33 -4 4 2 196.09 3.82 -2 4 2 114.48 4.31 0 4 2 213.47 6.66 2 4 2 807.74 11.02 4 4 2 1602.92 20.64 6 4 2 335.12 5.84 8 4 2 26.31 4.47 -5 5 2 381.67 6.65 -3 5 2 716.85 10.35 -1 5 2 105.89 10.86 1 5 2 344.80 7.29 3 5 2 44.20 2.82 5 5 2 158.01 4.25 -10 1 3 144.59 4.05 -8 1 3 1021.75 12.35 -6 1 3 4337.99 95.15 -4 1 3 20.61 3.83 -2 1 3 1427.08 32.84 0 1 3 913.39 49.29 2 1 3 1965.33 29.45 4 1 3 5533.35 94.34 6 1 3 30.02 2.76 8 1 3 975.11 11.93 10 1 3 341.64 7.43 -11 2 3 117.96 3.76 -9 2 3 926.11 12.92 -7 2 3 174.59 3.94 -5 2 3 3637.78 54.45 -3 2 3 4001.10 59.68 -1 2 3 3610.72 97.49 1 2 3 4175.67 72.50 3 2 3 2226.58 33.46 5 2 3 4228.83 84.23 7 2 3 306.33 5.39 9 2 3 260.84 5.29 -10 3 3 1396.86 31.46 -8 3 3 566.92 9.38 -6 3 3 2320.37 27.54 -4 3 3 1020.59 10.78 0 3 3 53.06 3.83 2 3 3 453.52 9.10 4 3 3 4258.53 49.70 6 3 3 50.23 3.15 8 3 3 1114.31 20.86 -7 4 3 439.24 9.30 -5 4 3 307.82 5.77 -3 4 3 174.17 3.90 -1 4 3 440.32 6.67 1 4 3 2714.06 30.64 3 4 3 2488.07 28.94 5 4 3 782.10 10.92 7 4 3 95.85 10.10 -6 5 3 52.29 3.25 -4 5 3 992.68 13.70 -2 5 3 8.97 2.31 0 5 3 253.98 5.63 2 5 3 386.57 6.48 4 5 3 203.67 5.01 -10 0 4 252.40 11.37 -8 0 4 3836.11 79.59 -6 0 4 3434.35 127.22 -4 0 4 229.39 5.78 -2 0 429606.30 622.95 0 0 4 89.07 2.64 2 0 4 216.50 5.07 4 0 4 3676.63 107.31 6 0 4 542.03 18.02 8 0 4 7564.38 105.31 10 0 4 226.43 11.43 -11 1 4 6.74 2.50 -9 1 4 25.49 3.05 -7 1 4 40.40 2.41 -5 1 4 4934.97 84.29 -3 1 410607.79 157.25 -1 1 451405.36 1869.90 1 1 415356.55 265.14 3 1 413069.05 221.71 5 1 4 1439.31 25.25 7 1 4 432.70 8.86 9 1 4 461.24 7.39 11 1 4 368.14 8.76 -10 2 4 12.12 2.38 -8 2 4 443.49 6.96 -6 2 4 67.08 2.93 -4 2 4 2.99 1.67 -2 2 4 380.02 7.23 0 2 4 746.50 13.71 2 2 4 697.66 13.32 4 2 4 21.73 1.60 6 2 4 473.02 11.81 8 2 4 415.22 6.81 10 2 4 15.03 2.60 -9 3 4 49.90 3.22 -7 3 4 384.96 5.89 -5 3 4 360.58 4.56 -3 3 4 75.72 2.19 -1 3 4 1351.90 28.90 1 3 4 211.26 7.63 3 3 4 506.43 8.86 5 3 4 189.12 3.54 7 3 4 92.77 3.83 9 3 4 3.49 2.83 -8 4 4 215.52 5.93 -6 4 4 877.15 14.99 -4 4 4 24.25 2.49 -2 4 4 827.33 11.26 0 4 4 121.03 2.98 2 4 4 75.55 3.80 4 4 4 13.02 3.77 6 4 4 641.07 11.01 8 4 4 460.11 18.85 -5 5 4 222.26 6.71 -3 5 4 23.06 2.76 -1 5 4 2116.77 27.02 1 5 4 910.46 12.59 3 5 4 15.51 2.71 5 5 4 241.15 6.48 -10 1 5 93.93 3.52 -8 1 5 13.44 2.10 -6 1 5 1209.55 31.51 -4 1 5 3980.21 59.27 -2 1 512904.31 242.32 0 1 5 1504.81 31.49 2 1 5 444.82 7.05 4 1 5 275.56 5.74 6 1 5 946.88 19.08 8 1 5 339.85 5.85 10 1 5 45.45 3.24 -11 2 5 339.88 10.34 -9 2 5 296.94 5.51 -7 2 5 89.02 7.51 -5 2 5 891.89 14.72 -3 2 5 69.54 4.02 -1 2 511046.51 244.73 1 2 5 426.41 8.23 3 2 5 2805.15 44.16 5 2 5 14.66 2.29 7 2 5 314.67 5.53 9 2 5 343.73 7.46 -10 3 5 787.48 13.33 -8 3 5 192.59 5.40 -6 3 5 120.45 4.48 -4 3 5 610.91 6.85 -2 3 5 3341.03 74.76 0 3 5 28.98 2.39 2 3 5 2068.20 36.62 4 3 5 44.79 4.83 6 3 5 677.82 9.84 8 3 5 486.26 11.44 -7 4 5 225.97 18.60 -5 4 5 267.15 5.02 -3 4 5 286.71 4.66 -1 4 5 1519.01 19.52 1 4 5 374.25 12.92 3 4 5 2415.27 26.16 5 4 5 9.37 2.26 7 4 5 33.34 4.07 -6 5 5 16.41 2.67 -4 5 5 509.70 13.17 -2 5 5 128.86 5.63 0 5 5 409.69 6.70 2 5 5 242.29 4.89 4 5 5 58.28 3.56 -12 0 6 171.43 7.31 -10 0 6 175.84 8.87 -8 0 6 256.12 16.95 -6 0 6 715.85 16.18 -4 0 6 1729.76 36.88 -2 0 6 3714.13 102.88 0 0 6 453.87 29.09 2 0 6 5428.68 114.31 4 0 6 2021.69 59.67 6 0 6 2296.20 68.24 8 0 6 189.28 5.73 10 0 6 1580.71 49.34 -11 1 6 159.74 4.36 -9 1 6 1020.78 12.45 -7 1 6 150.43 3.84 -5 1 6 6928.81 102.99 -3 1 6 6297.37 93.44 -1 1 6 8051.34 206.92 1 1 6 11.33 2.31 3 1 6 -2.03 2.25 5 1 6 1252.30 24.15 7 1 6 47.19 3.06 9 1 6 51.81 3.44 -10 2 6 3.74 2.29 -8 2 6 31.04 2.15 -6 2 6 766.56 9.69 -4 2 6 54.79 2.34 -2 2 6 168.15 6.43 0 2 6 816.89 58.16 2 2 6 124.05 3.64 4 2 6 112.76 3.73 6 2 6 1723.82 20.64 8 2 6 20.55 2.31 10 2 6 54.99 3.85 -9 3 6 4.58 2.34 -7 3 6 41.61 2.25 -5 3 6 709.65 7.87 -3 3 6 117.56 2.64 -1 3 6 946.53 17.45 1 3 6 811.57 24.52 3 3 6 227.29 6.45 5 3 6 30.66 1.98 7 3 6 44.07 3.03 9 3 6 119.71 4.67 -8 4 6 66.34 4.05 -6 4 6 151.50 4.72 -4 4 6 1142.39 14.02 -2 4 6 457.09 6.92 0 4 6 390.41 5.57 2 4 6 442.52 6.13 4 4 6 2.39 1.91 6 4 6 27.52 2.67 -5 5 6 552.62 12.13 -3 5 6 60.99 4.73 -1 5 6 333.12 7.92 1 5 6 35.20 9.77 3 5 6 655.30 10.55 5 5 6 579.49 10.30 -10 1 7 183.99 4.35 -8 1 7 753.15 10.44 -6 1 7 63.84 3.10 -4 1 7 74.11 2.66 -2 1 7 285.00 8.56 0 1 7 5398.83 154.38 2 1 723403.62 346.67 4 1 7 216.69 4.84 6 1 7 39.62 2.65 8 1 7 240.03 5.47 10 1 7 47.40 3.72 -11 2 7 1355.56 18.90 -9 2 7 287.26 5.38 -7 2 7 2441.18 28.78 -5 2 7 26.82 2.35 -3 2 7 115.67 2.83 -1 2 7 268.14 11.85 1 2 7 39.75 2.34 3 2 7 8987.32 148.84 5 2 7 983.01 15.11 7 2 7 784.89 11.05 9 2 7 432.78 7.29 -10 3 7 170.55 4.67 -8 3 7 882.34 12.10 -6 3 7 382.09 5.70 -4 3 7 1004.65 11.37 -2 3 7 3745.90 65.39 0 3 7 815.52 15.26 2 3 712043.47 256.54 4 3 7 499.97 7.54 6 3 7 1178.39 16.01 8 3 7 277.59 6.19 -7 4 7 1834.68 43.90 -5 4 7 13.30 2.00 -3 4 7 18.52 2.05 -1 4 7 72.15 5.51 1 4 7 617.76 7.72 3 4 7 1506.05 17.20 5 4 7 32.92 2.72 7 4 7 552.70 12.57 -6 5 7 27.46 3.00 -4 5 7 48.60 3.87 -2 5 7 1501.68 19.70 0 5 7 429.47 6.96 2 5 7 899.06 12.47 4 5 7 768.81 14.36 -12 0 8 28.56 4.56 -10 0 8 285.92 13.52 -8 0 8 2799.98 54.83 -6 0 8 202.38 10.19 -4 0 8 578.63 12.99 -2 0 815169.84 345.57 0 0 840533.55 1374.83 2 0 8 1369.19 29.19 4 0 8 8723.96 252.86 6 0 8 5003.54 146.21 8 0 8 54.26 4.21 10 0 8 325.33 14.18 -11 1 8 441.69 9.39 -9 1 8 881.22 12.14 -7 1 8 6337.17 81.55 -5 1 8 116.16 5.81 -3 1 8 272.49 5.78 -1 1 8 7.16 1.01 1 1 8 164.71 4.10 3 1 8 1411.40 21.39 5 1 8 1087.30 19.40 7 1 8 1471.27 19.31 9 1 8 580.03 15.10 -10 2 8 10.83 2.31 -8 2 8 118.51 3.24 -6 2 8 382.74 6.17 -4 2 8 1290.01 19.81 -2 2 8 12.92 1.55 0 2 8 3514.20 76.21 2 2 8 95.97 7.19 4 2 8 1460.93 23.43 6 2 8 20.49 2.07 8 2 8 235.59 4.95 -9 3 8 21.64 2.46 -7 3 8 187.17 3.86 -5 3 8 1210.17 13.59 -3 3 8 104.59 2.57 -1 3 8 26.64 5.27 1 3 8 996.60 38.12 3 3 8 466.14 6.51 5 3 8 19.79 2.20 7 3 8 2.85 2.60 -8 4 8 151.66 6.49 -6 4 8 38.18 4.41 -4 4 8 31.41 2.65 -2 4 8 580.09 7.69 0 4 8 784.20 9.08 2 4 8 429.47 6.04 4 4 8 37.77 3.02 6 4 8 783.26 17.74 -5 5 8 102.20 4.73 -3 5 8 832.12 11.77 -1 5 8 427.24 6.95 1 5 8 51.75 2.70 3 5 8 74.91 11.29 -12 1 9 80.88 9.23 -10 1 9 237.40 4.85 -8 1 9 186.09 3.92 -6 1 9 85.73 3.00 -4 1 9 3963.79 59.11 -2 1 9 108.62 2.40 0 1 9 18.91 1.34 2 1 9 5281.83 78.52 4 1 9 1776.07 30.86 6 1 9 598.07 9.85 8 1 9 87.33 3.94 10 1 9 16.70 2.96 -11 2 9 245.37 8.39 -9 2 9 758.46 10.84 -7 2 9 162.54 4.65 -5 2 9 95.76 3.09 -3 2 9 2142.10 32.29 -1 2 9 827.16 15.10 1 2 9 2028.30 39.20 3 2 9 438.79 7.40 5 2 9 34.50 2.16 7 2 9 1478.75 19.50 9 2 9 421.96 11.51 -10 3 9 260.34 5.56 -8 3 9 410.83 7.62 -6 3 9 3.46 4.45 -4 3 9 2644.20 28.48 -2 3 9 1233.18 16.27 0 3 9 2701.52 54.08 2 3 9 1713.91 29.45 4 3 9 167.54 3.49 6 3 9 44.44 2.87 8 3 9 6.04 2.87 -7 4 9 520.59 9.28 -5 4 9 9.75 2.00 -3 4 9 676.87 8.23 -1 4 9 255.40 4.28 1 4 9 475.24 6.10 3 4 9 14.08 2.88 5 4 9 108.83 5.44 7 4 9 158.94 6.02 -6 5 9 139.72 5.09 -4 5 9 306.43 5.76 -2 5 9 303.17 6.09 0 5 9 270.43 5.24 2 5 9 347.96 9.64 4 5 9 682.10 13.09 -12 0 10 31.75 4.75 -10 0 10 95.01 8.68 -8 0 10 427.27 17.28 -6 0 1012190.77 382.20 -4 0 1012811.24 268.58 -2 0 1013161.41 350.63 0 0 10 1385.24 52.17 2 0 10 289.09 6.90 4 0 10 2171.80 64.12 6 0 10 3041.27 50.36 8 0 10 198.84 5.98 10 0 10 486.32 15.85 -11 1 10 23.26 3.44 -9 1 10 302.69 7.04 -7 1 10 865.06 12.08 -5 1 10 511.36 8.45 -3 1 10 7707.07 114.20 -1 1 10 2745.96 81.28 1 1 10 1161.25 17.65 3 1 10 2325.84 34.92 5 1 10 330.98 5.46 7 1 10 2299.32 29.56 9 1 10 282.43 9.35 -10 2 10 71.76 3.46 -8 2 10 1069.33 13.34 -6 2 10 668.63 8.02 -4 2 10 137.67 3.33 -2 2 10 4358.73 75.67 0 2 10 24.86 2.57 2 2 10 67.52 3.60 4 2 10 14.66 1.73 6 2 10 525.11 7.08 8 2 10 -0.01 2.96 -9 3 10 193.25 5.15 -7 3 10 65.40 3.09 -5 3 10 1249.80 14.01 -3 3 10 806.62 9.94 -1 3 10 154.92 3.81 1 3 10 6.78 1.95 3 3 10 442.47 5.72 5 3 10 314.81 5.82 7 3 10 2.06 2.60 -8 4 10 76.82 4.14 -6 4 10 349.99 6.02 -4 4 10 222.62 3.85 -2 4 10 17.60 2.24 0 4 10 216.04 3.95 2 4 10 282.04 4.31 4 4 10 1343.63 18.60 6 4 10 187.72 7.57 -5 5 10 62.07 3.37 -3 5 10 590.66 12.05 -1 5 10 8.15 2.57 1 5 10 325.06 6.31 3 5 10 299.92 7.40 -12 1 11 71.80 4.99 -10 1 11 122.75 4.25 -8 1 11 397.29 6.52 -6 1 11 1037.81 16.26 -4 1 11 118.44 3.91 -2 1 11 1251.47 19.65 0 1 11 2363.52 41.27 2 1 11 506.45 8.13 4 1 11 14.04 1.82 6 1 11 552.77 8.15 8 1 11 911.29 12.79 10 1 11 693.96 12.09 -11 2 11 39.14 5.21 -9 2 11 91.90 3.38 -7 2 11 59.66 2.48 -5 2 11 2073.21 31.45 -3 2 11 9369.75 161.75 -1 2 11 613.68 11.58 1 2 1111461.86 197.88 3 2 11 1090.13 16.90 5 2 11 1346.14 16.35 7 2 11 105.64 4.76 9 2 11 12.38 3.30 -10 3 11 624.51 11.07 -8 3 11 305.41 5.71 -6 3 11 1699.77 20.65 -4 3 11 283.69 4.44 -2 3 11 534.91 7.76 0 3 11 480.79 7.08 2 3 11 1522.60 22.98 4 3 11 1230.79 17.00 6 3 11 139.89 4.39 8 3 11 467.12 19.38 -7 4 11 389.41 13.64 -5 4 11 74.24 4.55 -3 4 11 1176.08 13.39 -1 4 11 67.61 2.65 1 4 11 5371.10 55.90 3 4 11 491.67 6.97 5 4 11 912.24 17.98 -4 5 11 30.56 6.59 -2 5 11 8.77 3.75 0 5 11 49.38 2.99 2 5 11 148.59 4.83 -12 0 12 513.39 15.55 -10 0 12 316.85 9.97 -8 0 12 6228.18 126.10 -6 0 12 40.12 3.75 -4 0 1211520.07 241.56 -2 0 12 1138.24 24.53 0 0 1225894.12 541.63 2 0 12 54.57 2.85 4 0 12 1788.18 53.19 6 0 12 2077.08 35.00 8 0 12 1083.68 24.42 10 0 12 19.10 4.16 -11 1 12 138.51 4.07 -9 1 12 1105.60 14.87 -7 1 12 30.77 2.49 -5 1 12 359.87 6.35 -3 1 12 100.46 6.50 -1 1 12 1586.82 23.94 1 1 1221201.88 313.80 3 1 12 1024.36 15.81 5 1 12 4719.19 59.21 7 1 12 329.71 5.82 9 1 12 327.01 12.41 -10 2 12 42.98 2.68 -8 2 12 2336.35 27.71 -6 2 12 6.24 1.87 -4 2 12 51.94 2.46 -2 2 12 1013.39 18.44 0 2 12 690.66 16.08 2 2 12 507.08 17.21 4 2 12 780.72 12.42 6 2 12 108.60 3.91 8 2 12 61.83 4.62 -9 3 12 17.09 2.58 -7 3 12 11.31 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2 3 27 30.81 3.51 -5 4 27 6.39 2.67 -3 4 27 349.85 6.06 -1 4 27 273.88 5.80 -10 0 28 71.58 4.86 -8 0 28 361.74 7.39 -6 0 28 989.74 15.57 -4 0 28 271.47 5.95 -2 0 28 263.46 5.77 0 0 28 356.89 7.87 2 0 28 4.14 3.12 4 0 28 2730.41 127.33 -9 1 28 336.00 5.39 -7 1 28 1430.97 18.09 -5 1 28 145.98 3.50 -3 1 28 159.79 4.54 -1 1 28 223.21 4.32 1 1 28 474.78 7.52 3 1 28 285.84 7.05 5 1 28 823.70 24.91 -8 2 28 -1.18 2.44 -6 2 28 5.08 2.58 -4 2 28 453.85 7.01 -2 2 28 95.14 3.60 0 2 28 230.17 4.56 2 2 28 290.67 6.14 4 2 28 318.42 7.90 -7 3 28 11.65 2.63 -5 3 28 10.49 2.75 -3 3 28 9.83 2.43 -1 3 28 85.96 3.85 1 3 28 18.56 3.55 3 3 28 43.77 4.26 -4 4 28 24.17 2.82 -2 4 28 435.05 7.04 0 4 28 140.09 6.64 -10 1 29 20.75 2.78 -8 1 29 170.46 3.83 -6 1 29 151.68 3.72 -4 1 29 43.89 2.62 -2 1 29 325.74 5.34 0 1 29 760.77 10.11 2 1 29 37.08 3.23 4 1 29 128.41 5.43 -9 2 29 483.90 9.34 -7 2 29 5.26 2.45 -5 2 29 648.54 10.12 -3 2 29 1428.43 19.95 -1 2 29 13.86 2.41 1 2 29 689.62 9.53 3 2 29 189.38 5.50 -8 3 29 94.20 5.13 -6 3 29 55.48 3.57 -4 3 29 182.90 4.86 -2 3 29 335.99 6.53 0 3 29 1750.29 26.83 2 3 29 137.70 7.20 -3 4 29 144.20 4.23 -10 0 30 23.70 3.62 -8 0 30 6.09 3.07 -6 0 30 315.26 8.07 -4 0 30 1325.39 20.32 -2 0 30 5552.23 83.60 0 0 30 52.98 3.93 2 0 30 907.82 19.83 4 0 30 2086.66 128.24 -9 1 30 465.48 6.71 -7 1 30 12.64 2.32 -5 1 30 3276.31 40.01 -3 1 30 477.16 7.42 -1 1 30 706.32 9.53 1 1 30 17.95 2.53 3 1 30 2.42 3.58 -8 2 30 -2.57 2.57 -6 2 30 368.82 7.18 -4 2 30 2.78 2.42 -2 2 30 457.97 7.75 0 2 30 18.47 2.62 2 2 30 309.57 6.75 4 2 30 635.75 12.77 -7 3 30 166.02 4.99 -5 3 30 42.80 3.29 -3 3 30 91.84 4.00 -1 3 30 113.05 5.14 1 3 30 43.84 3.47 -10 1 31 27.64 6.98 -8 1 31 48.58 2.98 -6 1 31 55.17 3.09 -4 1 31 97.64 3.57 -2 1 31 317.43 5.39 0 1 31 316.02 5.45 2 1 31 358.89 8.27 4 1 31 0.49 4.22 -9 2 31 59.08 3.86 -7 2 31 117.47 4.41 -5 2 31 831.15 12.50 -3 2 31 36.01 3.71 -1 2 31 2062.65 28.17 1 2 31 398.37 7.09 3 2 31 19.59 3.58 -6 3 31 626.55 10.26 -4 3 31 44.48 3.26 -2 3 31 504.22 8.65 0 3 31 798.21 13.69 -10 0 32 34.18 7.91 -8 0 32 1117.14 17.78 -6 0 32 429.99 10.00 -4 0 32 109.84 4.53 -2 0 32 350.06 7.07 0 0 32 94.31 4.79 2 0 32 2801.96 75.33 4 0 32 16.93 4.82 -9 1 32 155.61 4.99 -7 1 32 30.17 3.25 -5 1 32 131.57 3.98 -3 1 32 14.87 2.49 -1 1 32 82.65 3.39 1 1 32 1277.88 17.56 3 1 32 291.12 7.57 -8 2 32 116.07 5.30 -6 2 32 56.92 3.84 -4 2 32 51.65 3.07 -2 2 32 304.94 6.19 0 2 32 119.88 3.94 2 2 32 196.59 5.09 -5 3 32 0.63 2.95 -3 3 32 346.83 6.84 -1 3 32 679.75 10.91 1 3 32 -1.70 4.37 -8 1 33 333.56 6.66 -6 1 33 44.44 3.35 -4 1 33 32.42 2.76 -2 1 33 30.95 2.51 0 1 33 575.72 8.34 2 1 33 203.33 6.38 -7 2 33 71.00 4.20 -5 2 33 121.37 4.34 -3 2 33 3.13 2.65 -1 2 33 1653.79 25.43 1 2 33 62.36 3.71 -6 3 33 7.25 6.32 -4 3 33 320.45 6.76 -2 3 33 531.79 13.10 0 3 33 666.00 13.78 -8 0 34 241.31 7.72 -6 0 34 1200.92 22.83 -4 0 34 1288.84 24.23 -2 0 34 102.95 4.46 0 0 34 142.06 5.67 2 0 34 52.56 7.42 -9 1 34 96.24 7.35 -7 1 34 117.55 4.79 -5 1 34 9.11 2.69 -3 1 34 132.99 3.99 -1 1 34 555.93 8.12 1 1 34 452.50 8.36 -6 2 34 156.63 4.86 -4 2 34 77.79 3.78 -2 2 34 4.30 3.00 0 2 34 122.43 4.49 -5 3 34 8.19 6.43 -3 3 34 3.63 3.12 -8 1 35 46.48 3.58 -6 1 35 550.55 9.60 -4 1 35 456.36 7.35 -2 1 35 103.09 3.57 0 1 35 12.51 2.88 2 1 35 3.16 3.52 -7 2 35 600.55 10.07 -5 2 35 238.72 5.67 -3 2 35 449.00 8.69 -1 2 35 83.21 4.25 1 2 35 163.93 5.31 -8 0 36 21.06 4.47 -6 0 36 222.05 7.49 -4 0 36 51.30 6.29 -2 0 36 3.60 3.29 0 0 36 792.25 26.70 2 0 36 327.75 13.63 -7 1 36 730.71 12.04 -5 1 36 8.34 2.88 -3 1 36 785.75 11.05 -1 1 36 353.12 6.23 1 1 36 219.41 5.46 -6 2 36 0.03 3.16 -4 2 36 2.38 2.85 -2 2 36 101.88 4.52 0 2 36 16.14 3.42 -6 1 37 2.87 3.39 -4 1 37 15.61 2.92 -2 1 37 739.26 11.75 0 1 37 745.75 11.28 -5 2 37 210.57 5.58 -3 2 37 943.07 23.05 -1 2 37 -2.80 3.28 -6 0 38 299.91 8.70 -4 0 38 64.46 5.60 -2 0 38 1202.52 33.45 0 0 38 216.79 7.23 -5 1 38 92.98 4.18 -3 1 38 695.40 10.18 -1 1 38 109.78 4.14 -4 2 38 251.39 10.36 -4 1 39 3.59 3.07 -2 1 39 6.30 3.09 -4 0 40 197.34 12.09 -2 0 40 175.28 6.72 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 95601 _shelx_res_file ; TITL DLMETA05 CELL 0.71073 9.877 4.6915 32.603 90.000 106.250 90.000 ZERR 8.00 0.002 0.0010 0.006 0.000 0.010 0.000 LATT 2 SYMM 1/2-x,y,-z SFAC C H N O S UNIT 40 88 8 16 8 TEMP -168 L.S. 10 FMAP 2 PLAN 5 ACTA BOND $H CONF RTAB HTOR C1 C2 N1 H1 RTAB HTOR C1 C2 N1 H2 RTAB HTOR C1 C2 N1 H3 EQIV $1 -X, 0.5 + Y, 0.5 - Z EQIV $2 0.5 + X, 1 - Y, Z EQIV $3 0.5 + X, -Y, Z HTAB N1 O2_$1 HTAB N1 O1_$2 HTAB N1 O1_$3 WGHT 0.023300 2.478200 FVAR 1.00132 S1 5 0.396515 0.156815 0.442918 11.00000 0.03507 0.03373 = 0.02313 0.00738 -0.00305 -0.00672 O1 4 -0.145227 0.202493 0.314026 11.00000 0.02249 0.01678 = 0.03333 -0.00032 0.00888 0.00116 O2 4 -0.018405 -0.081037 0.284106 11.00000 0.02527 0.01562 = 0.02224 -0.00277 0.00375 -0.00101 N1 3 0.192961 0.300017 0.297326 11.00000 0.02073 0.01686 = 0.01898 0.00084 0.00345 -0.00097 H1 2 0.142095 0.331542 0.270974 11.00000 -1.50000 H2 2 0.237811 0.122348 0.299910 11.00000 -1.50000 H3 2 0.263134 0.435837 0.305422 11.00000 -1.50000 C1 1 -0.032890 0.130148 0.305618 11.00000 0.02132 0.01382 = 0.01815 0.00338 0.00193 0.00061 C2 1 0.099673 0.308727 0.325888 11.00000 0.02116 0.01282 = 0.02082 -0.00080 0.00594 0.00050 AFIX 13 H4 2 0.071879 0.510301 0.329369 11.00000 -1.20000 AFIX 0 C3 1 0.176391 0.183149 0.369818 11.00000 0.02477 0.01863 = 0.01969 -0.00022 0.00434 -0.00080 AFIX 23 H5 2 0.114792 0.203806 0.388932 11.00000 -1.20000 H6 2 0.191083 -0.023238 0.366396 11.00000 -1.20000 AFIX 0 C4 1 0.319636 0.321380 0.391428 11.00000 0.02733 0.02157 = 0.02129 0.00168 0.00071 -0.00155 AFIX 23 H7 2 0.306837 0.528058 0.395211 11.00000 -1.20000 H8 2 0.383685 0.297309 0.373129 11.00000 -1.20000 AFIX 0 C5 1 0.565949 0.332591 0.458300 11.00000 0.03087 0.04163 = 0.02724 0.00122 -0.00077 -0.00244 AFIX 33 H9 2 0.620757 0.262723 0.486363 11.00000 -1.50000 H10 2 0.616894 0.291619 0.437139 11.00000 -1.50000 H11 2 0.552125 0.538803 0.459744 11.00000 -1.50000 AFIX 0 HKLF 4 REM DLMETA05 REM R1 = 0.0377 for 1373 Fo > 4sig(Fo) and 0.0389 for all 1436 data REM 92 parameters refined using 0 restraints END WGHT 0.0230 2.4918 REM Highest difference peak 0.349, deepest hole -0.229, 1-sigma level 0.050 Q1 1 0.3694 0.1823 0.4110 11.00000 0.05 0.35 Q2 1 0.1417 0.2502 0.3481 11.00000 0.05 0.28 Q3 1 0.5451 0.3256 0.4264 11.00000 0.05 0.26 Q4 1 0.0225 0.2544 0.3109 11.00000 0.05 0.25 Q5 1 0.2418 0.2677 0.3798 11.00000 0.05 0.22 ; _shelx_res_checksum 53088 _shelxl_version_number 2014-3 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -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 S S1 0.39652(6) 0.15681(12) 0.44292(2) 0.03291(18) Uani d 1 O O1 -0.14523(13) 0.2025(3) 0.31403(4) 0.0240(3) Uani d 1 O O2 -0.01841(13) -0.0810(3) 0.28411(4) 0.0216(3) Uani d 1 N N1 0.19296(17) 0.3000(3) 0.29733(5) 0.0193(3) Uani d 1 H H1 0.142(3) 0.332(5) 0.2710(8) 0.029 Uiso d 1 H H2 0.238(2) 0.122(6) 0.2999(7) 0.029 Uiso d 1 H H3 0.263(2) 0.436(5) 0.3054(7) 0.029 Uiso d 1 C C1 -0.03289(18) 0.1301(4) 0.30562(5) 0.0185(4) Uani d 1 C C2 0.09967(18) 0.3087(4) 0.32589(5) 0.0183(4) Uani d 1 H H4 0.0719 0.5103 0.3294 0.022 Uiso calc 1 C C3 0.17639(19) 0.1831(4) 0.36982(5) 0.0214(4) Uani d 1 H H5 0.1148 0.2038 0.3889 0.026 Uiso calc 1 H H6 0.1911 -0.0232 0.3664 0.026 Uiso calc 1 C C4 0.3196(2) 0.3214(4) 0.39143(6) 0.0246(4) Uani d 1 H H7 0.3068 0.5281 0.3952 0.030 Uiso calc 1 H H8 0.3837 0.2973 0.3731 0.030 Uiso calc 1 C C5 0.5659(2) 0.3326(5) 0.45830(7) 0.0350(5) Uani d 1 H H9 0.6208 0.2627 0.4864 0.053 Uiso calc 1 H H10 0.6169 0.2916 0.4371 0.053 Uiso calc 1 H H11 0.5521 0.5388 0.4597 0.053 Uiso calc 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 S1 0.0351(3) 0.0337(3) 0.0231(3) -0.0067(2) -0.0031(2) 0.0074(2) O1 0.0225(7) 0.0168(6) 0.0333(7) 0.0012(5) 0.0089(5) -0.0003(5) O2 0.0253(7) 0.0156(6) 0.0222(6) -0.0010(5) 0.0037(5) -0.0028(5) N1 0.0207(7) 0.0169(8) 0.0190(7) -0.0010(6) 0.0035(6) 0.0008(6) C1 0.0213(8) 0.0138(8) 0.0181(8) 0.0006(7) 0.0019(7) 0.0034(6) C2 0.0212(8) 0.0128(8) 0.0208(8) 0.0005(7) 0.0059(7) -0.0008(7) C3 0.0248(9) 0.0186(9) 0.0197(8) -0.0008(7) 0.0043(7) -0.0002(7) C4 0.0273(10) 0.0216(9) 0.0213(9) -0.0016(8) 0.0007(7) 0.0017(7) C5 0.0309(11) 0.0416(13) 0.0272(10) -0.0024(9) -0.0008(8) 0.0012(9) 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 S1 C4 100.27(10) C2 N1 H1 108.9(15) C2 N1 H2 109.2(14) H1 N1 H2 111(2) C2 N1 H3 110.5(14) H1 N1 H3 110(2) H2 N1 H3 107(2) O2 C1 O1 125.67(17) O2 C1 C2 117.19(15) O1 C1 C2 117.03(15) N1 C2 C3 110.09(14) N1 C2 C1 108.59(14) C3 C2 C1 109.25(14) N1 C2 H4 109.6 C3 C2 H4 109.6 C1 C2 H4 109.6 C4 C3 C2 114.57(15) C4 C3 H5 108.6 C2 C3 H5 108.6 C4 C3 H6 108.6 C2 C3 H6 108.6 H5 C3 H6 107.6 C3 C4 S1 109.80(13) C3 C4 H7 109.7 S1 C4 H7 109.7 C3 C4 H8 109.7 S1 C4 H8 109.7 H7 C4 H8 108.2 S1 C5 H9 109.5 S1 C5 H10 109.5 H9 C5 H10 109.5 S1 C5 H11 109.5 H9 C5 H11 109.5 H10 C5 H11 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C5 1.806(2) S1 C4 1.8104(19) O1 C1 1.262(2) O2 C1 1.245(2) N1 C2 1.483(2) N1 H1 0.88(3) N1 H2 0.94(3) N1 H3 0.92(3) C1 C2 1.539(2) C2 C3 1.538(2) C2 H4 1.0000 C3 C4 1.536(2) C3 H5 0.9900 C3 H6 0.9900 C4 H7 0.9900 C4 H8 0.9900 C5 H9 0.9800 C5 H10 0.9800 C5 H11 0.9800 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 _geom_hbond_publ_flag N1 H1 O2 4_455 0.88(3) 1.91(3) 2.788(2) 175(3) n N1 H2 O1 6_655 0.94(3) 1.89(3) 2.815(2) 169(2) n N1 H3 O1 6_665 0.92(2) 1.91(2) 2.795(2) 161(2) n C2 H4 O2 1_565 1.00 2.43 3.244(2) 138 n 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_publ_flag N1 C2 C3 C4 54.4(2) y C1 C2 C3 C4 173.53(15) y C2 C3 C4 S1 179.23(12) y C3 C4 S1 C5 175.03(14) y O2 C1 C2 N1 32.5(2) ? O1 C1 C2 N1 -150.93(15) ? O2 C1 C2 C3 -87.60(18) ? O1 C1 C2 C3 88.98(18) ? C1 C2 N1 H1 46.5(17) y C1 C2 N1 H2 -75.3(15) y C1 C2 N1 H3 167.4(15) y _cod_database_fobs_code 2240074