#------------------------------------------------------------------------------ #$Date: 2022-09-01 05:09:25 +0300 (Thu, 01 Sep 2022) $ #$Revision: 277533 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244154.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_2244154 loop_ _publ_author_name 'Irrou, Ezaddine' 'Elmachkouri, Younesse Ait' 'Oubella, Ali' 'Ouchtak, Hassan' 'Dalbouha, Samira' 'Mague, Joel T.' 'H\"okelek, Tuncer' 'El Ghayati, Lhoussaine' 'Sebbar, Nada Kheira' 'Taha, Mohamed Labd' _publ_section_title ; Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid ; _journal_coeditor_code WM5656 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 953 _journal_page_last 960 _journal_paper_doi 10.1107/S2056989022008489 _journal_volume 78 _journal_year 2022 _chemical_formula_iupac 'C7 H6 N4 O3' _chemical_formula_moiety 'C7 H6 N4 O3' _chemical_formula_sum 'C7 H6 N4 O3' _chemical_formula_weight 194.16 _chemical_name_systematic ; 2-(4-Oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic 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 mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _cell_angle_alpha 90 _cell_angle_beta 103.1220(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.3747(4) _cell_length_b 4.66990(10) _cell_length_c 23.0423(5) _cell_measurement_reflns_used 5261 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 74.4099 _cell_measurement_theta_min 3.9398 _cell_volume 1611.20(6) _computing_cell_refinement ; SAINT (Bruker, 2016) ; _computing_data_collection ; APEX3 (Bruker, 2016) ; _computing_data_reduction ; SAINT (Bruker, 2016) ; _computing_molecular_graphics ; DIAMOND (Brandenburg & Putz, 2012) ; _computing_publication_material ; publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON 100 CMOS' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0260 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 5850 _diffrn_reflns_theta_full 68.000 _diffrn_reflns_theta_max 74.402 _diffrn_reflns_theta_min 3.940 _diffrn_source 'INCOATEC I\mS micro--focus source' _exptl_absorpt_coefficient_mu 1.111 _exptl_absorpt_correction_T_max 0.89 _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Krause et al., 2015) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.236 _exptl_crystal_size_mid 0.176 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.248 _refine_diff_density_min -0.329 _refine_ls_extinction_coef 0.0304(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL 2018/3 (Sheldrick, 2015b) ; _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1598 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.155 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0476 _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^)+(0.0630P)^2^+0.6265P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1124 _refine_ls_wR_factor_ref 0.1143 _reflns_number_gt 1503 _reflns_number_total 1598 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5656sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2244154 _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_estimated_absorpt_t_min 0.780 _shelx_estimated_absorpt_t_max 0.888 _shelx_hkl_file ; 2 0 0 2440.36 84.79 -6 0 0 17.20 1.20 -8 0 0 846.92 31.50 -8 0 0 927.51 31.60 8 0 0 890.81 31.60 10 0 0 104.19 4.60 10 0 0 97.29 4.90 10 0 0 102.89 5.20 12 0 0 9.40 2.00 12 0 0 11.90 1.90 12 0 0 8.40 2.10 14 0 0 142.79 6.50 14 0 0 132.99 6.20 14 0 0 134.09 6.00 16 0 0 293.37 11.60 16 0 0 295.47 11.40 18 0 0 17.20 1.40 18 0 0 16.60 1.60 1 -1 0 2951.60 102.69 3 -1 0 129.39 4.90 -3 -1 0 138.59 5.50 3 -1 0 139.09 4.90 -5 -1 0 7008.10 244.08 -7 -1 0 82.39 4.10 -7 -1 0 74.19 4.40 7 -1 0 79.49 3.60 7 1 0 77.99 3.50 9 -1 0 1444.86 50.89 -9 -1 0 1373.96 51.49 9 -1 0 1500.15 51.29 9 -1 0 1423.56 50.59 9 1 0 1415.76 50.69 11 -1 0 318.67 11.80 11 -1 0 308.97 12.10 11 -1 0 299.97 12.40 11 1 0 293.77 12.00 11 1 0 322.47 11.90 11 1 0 291.57 12.30 13 -1 0 161.08 7.30 13 -1 0 154.88 7.00 13 -1 0 158.88 6.80 13 1 0 155.88 6.90 13 1 0 155.08 7.20 13 1 0 158.28 6.90 15 -1 0 317.47 12.20 15 -1 0 292.67 11.80 15 1 0 288.87 11.70 15 1 0 294.17 11.50 17 -1 0 25.00 1.80 17 -1 0 25.70 1.70 17 1 0 18.20 2.40 0 -2 0 2308.77 80.49 0 -2 0 2271.37 80.49 -2 -2 0 67.59 3.90 2 -2 0 70.69 3.40 2 -2 0 73.89 3.30 2 -2 0 72.39 3.30 -2 -2 0 69.39 3.60 2 2 0 73.09 3.30 -4 -2 0 2377.16 79.99 4 -2 0 2152.78 79.09 4 -2 0 2231.78 78.89 4 -2 0 2245.98 78.89 4 2 0 2284.67 79.19 -6 -2 0 8.20 3.30 6 -2 0 12.10 1.40 6 2 0 9.90 1.50 8 -2 0 102.89 4.40 8 -2 0 94.29 5.10 8 -2 0 90.89 5.10 8 2 0 99.59 4.40 -8 2 0 84.59 5.20 8 2 0 92.99 4.70 10 -2 0 67.09 4.30 10 -2 0 67.99 3.60 10 -2 0 69.89 4.10 10 2 0 63.99 3.80 10 2 0 72.69 3.80 -10 2 0 73.39 5.20 12 -2 0 8.80 2.10 12 -2 0 12.20 1.90 12 -2 0 13.50 2.10 12 2 0 10.70 2.20 14 -2 0 0.20 1.30 14 -2 0 0.80 1.30 14 -2 0 1.80 1.60 16 -2 0 8.40 1.30 16 -2 0 9.70 1.30 1 -3 0 11.50 1.50 1 -3 0 15.10 4.30 -1 3 0 10.50 2.90 1 3 0 9.70 2.30 1 3 0 8.90 2.20 -1 3 0 8.70 2.30 3 -3 0 0.00 0.70 -3 3 0 -1.60 1.30 3 3 0 0.50 1.10 3 3 0 -0.90 1.20 5 -3 0 317.37 12.60 -5 3 0 345.17 13.00 5 3 0 318.17 12.50 5 3 0 330.57 12.80 5 3 0 318.97 12.60 7 -3 0 126.59 5.60 7 3 0 118.29 5.80 -7 3 0 120.49 6.40 7 3 0 119.79 5.50 7 3 0 119.79 5.60 9 -3 0 25.30 3.20 9 -3 0 28.30 2.60 -9 3 0 30.60 2.90 9 3 0 23.80 2.40 9 3 0 29.50 2.40 11 -3 0 240.38 11.00 11 -3 0 235.88 9.40 11 -3 0 233.08 9.60 11 3 0 218.78 9.30 -11 3 0 230.88 9.70 11 3 0 235.98 9.30 13 -3 0 19.00 2.20 13 -3 0 23.50 2.20 13 -3 0 23.70 2.70 0 4 0 60.19 3.50 0 4 0 61.49 3.70 2 -4 0 341.57 13.40 -2 -4 0 332.77 13.10 -2 4 0 326.77 13.20 2 4 0 332.67 13.10 -2 4 0 319.27 12.80 2 4 0 327.67 12.90 4 -4 0 36.60 2.70 -4 4 0 37.30 2.90 4 4 0 39.30 2.90 4 4 0 30.50 2.60 6 -4 0 34.90 2.60 6 4 0 36.40 2.70 -6 4 0 34.10 2.70 8 -4 0 163.48 7.40 8 4 0 174.68 7.40 -8 4 0 187.38 7.70 8 4 0 186.18 7.50 10 -4 0 131.59 6.00 -10 4 0 129.79 5.70 10 4 0 125.49 5.50 12 4 0 45.90 2.40 1 -5 0 146.99 6.40 -1 -5 0 153.28 6.60 1 5 0 143.59 6.10 1 5 0 142.89 6.40 -1 5 0 149.09 6.10 -1 5 0 142.89 6.40 3 -5 0 643.04 24.10 -3 -5 0 658.33 24.10 3 5 0 660.13 24.10 3 5 0 674.13 23.90 -3 5 0 655.23 24.20 5 -5 0 18.70 1.80 -5 -5 0 17.50 1.90 -5 5 0 17.60 1.70 5 5 0 18.60 1.70 5 5 0 15.80 1.40 7 -5 0 199.78 8.00 -7 -5 0 206.98 8.10 7 5 0 205.08 7.80 -7 5 0 208.78 7.90 7 5 0 196.58 7.90 9 5 0 1.20 0.50 18 0 -1 -1.10 0.80 18 0 -1 -1.10 0.90 16 0 -1 0.40 0.80 16 0 -1 1.20 0.90 14 0 -1 -1.10 1.10 14 0 -1 2.10 1.50 14 0 -1 -0.20 0.90 12 0 -1 -1.80 1.10 12 0 -1 -1.00 1.10 10 0 -1 -0.50 1.10 10 0 -1 -0.80 1.00 10 0 -1 -3.00 1.50 8 0 -1 -0.90 0.70 -8 0 1 0.40 0.70 -8 0 1 -0.60 0.70 -6 0 1 0.40 0.40 -6 0 1 0.60 0.40 -4 0 1 -0.20 0.20 2 0 1 0.30 0.20 -2 0 -1 0.30 0.10 4 0 1 0.30 0.30 -4 0 -1 0.30 0.30 -6 0 -1 0.40 0.40 8 0 1 0.50 0.70 -8 0 -1 0.70 1.00 10 0 1 -1.00 1.00 10 0 1 0.60 1.20 10 0 1 -0.90 0.90 12 0 1 1.30 1.00 12 0 1 -0.40 1.20 12 0 1 0.90 1.00 14 0 1 -0.80 1.10 14 0 1 -0.90 1.10 14 0 1 0.10 0.90 16 0 1 0.90 0.90 16 0 1 -0.40 0.70 18 0 1 0.50 0.60 17 -1 -1 202.88 8.30 17 -1 -1 209.38 8.10 17 1 -1 203.98 8.00 15 -1 -1 73.49 3.90 15 -1 -1 72.49 4.60 15 1 -1 66.99 3.80 15 1 -1 64.39 4.00 13 -1 -1 1529.35 59.79 13 -1 -1 1668.53 60.39 13 -1 -1 1682.23 59.89 13 1 -1 1759.62 59.39 13 1 -1 1696.63 59.59 13 1 -1 1672.63 59.79 11 -1 -1 23.90 2.00 11 -1 -1 20.10 2.40 11 -1 -1 17.80 2.30 11 1 -1 18.90 2.20 11 1 -1 19.60 2.60 11 1 -1 17.60 3.00 9 -1 -1 616.44 22.10 -9 -1 1 614.14 23.00 9 -1 -1 616.64 22.70 9 -1 -1 603.24 22.50 9 1 -1 599.54 22.10 7 -1 -1 2472.95 88.99 -7 -1 1 2786.12 89.69 -7 -1 1 2443.06 89.59 7 1 -1 2476.25 88.99 -5 -1 1 3275.67 113.89 -5 -1 1 3231.08 113.89 -3 -1 1 4119.79 143.59 -1 -1 1 4634.64 161.28 1 -1 1 3135.09 109.09 -3 -1 -1 3014.10 104.59 3 -1 1 2947.51 103.59 5 -1 1 44.40 2.50 -5 -1 -1 48.70 2.70 7 -1 1 650.33 23.30 -7 -1 -1 637.44 24.00 7 1 1 656.23 23.30 9 -1 1 275.07 10.30 9 -1 1 272.77 10.70 9 -1 1 273.67 10.90 -9 -1 -1 265.97 11.90 9 1 1 257.67 10.70 9 1 1 266.17 10.30 11 -1 1 697.53 29.30 11 -1 1 802.22 28.60 11 -1 1 823.32 28.30 11 1 1 759.82 28.60 11 1 1 772.92 28.40 11 1 1 820.92 28.40 13 -1 1 3.30 1.20 13 -1 1 5.50 1.30 13 -1 1 4.20 1.40 13 1 1 5.20 1.60 13 1 1 7.30 1.90 13 1 1 4.40 1.20 15 -1 1 5.90 1.50 15 -1 1 8.80 2.10 15 -1 1 10.20 3.00 15 1 1 11.90 2.80 15 1 1 5.80 1.60 15 1 1 7.10 1.60 17 -1 1 8.40 1.40 17 -1 1 9.20 1.20 17 1 1 10.10 1.50 16 -2 -1 12.40 1.40 16 -2 -1 12.20 1.50 14 -2 -1 165.18 7.00 14 -2 -1 162.68 7.30 14 -2 -1 150.78 6.80 12 -2 -1 3.80 1.10 12 -2 -1 5.70 1.30 12 -2 -1 3.40 1.30 12 2 -1 4.00 1.50 10 -2 -1 6.50 1.60 10 -2 -1 8.80 2.30 10 -2 -1 3.80 1.10 10 2 -1 2.40 1.20 10 2 -1 3.80 1.10 -10 2 1 7.70 2.00 8 -2 -1 414.26 16.20 8 -2 -1 414.86 16.00 8 -2 -1 443.06 15.70 8 2 -1 446.16 15.70 8 2 -1 418.76 15.80 8 2 -1 384.66 16.10 6 -2 -1 141.99 5.70 -6 -2 1 135.79 6.90 6 2 -1 130.99 5.60 4 -2 -1 91.69 4.20 4 -2 -1 99.49 3.90 -4 -2 1 102.59 5.00 4 -2 -1 103.59 4.00 4 2 -1 93.19 4.20 2 -2 -1 745.43 27.40 -2 -2 1 765.22 27.80 -2 -2 1 773.72 28.00 2 -2 -1 736.23 27.30 2 2 -1 809.22 27.40 0 -2 1 354.96 12.60 0 -2 -1 329.07 12.60 0 -2 1 324.17 12.70 0 -2 -1 315.97 12.60 0 2 1 343.07 12.40 2 -2 1 615.04 22.10 -2 -2 -1 625.94 22.70 2 -2 1 610.74 22.10 -2 -2 -1 616.44 22.50 2 -2 1 666.83 22.30 2 2 1 551.54 22.00 4 -2 1 1521.05 54.39 4 -2 1 1610.34 54.49 4 -2 1 1529.25 54.59 -4 -2 -1 1573.54 55.39 4 2 1 1522.45 54.59 6 -2 1 1233.28 47.20 -6 -2 -1 1382.96 47.80 6 2 1 1327.17 46.60 8 -2 1 207.98 8.90 8 -2 1 214.28 9.00 8 -2 1 216.78 8.50 8 2 1 224.08 8.50 8 2 1 206.68 8.60 -8 2 -1 193.68 9.20 10 -2 1 112.39 5.10 10 -2 1 119.39 6.80 10 -2 1 104.69 5.60 10 2 1 110.59 5.20 12 -2 1 44.20 3.20 12 -2 1 38.00 2.70 12 -2 1 35.70 2.80 12 2 1 36.40 2.70 14 -2 1 4.80 1.70 14 -2 1 3.50 1.00 14 -2 1 3.40 1.20 14 2 1 1.70 1.60 16 -2 1 1.90 0.70 16 -2 1 2.50 0.80 13 -3 -1 51.19 3.20 13 -3 -1 52.09 3.10 13 -3 -1 51.59 3.20 11 -3 -1 34.90 3.10 11 -3 -1 34.40 2.50 -11 3 1 43.50 3.10 11 3 -1 33.50 2.50 11 3 -1 35.70 2.70 9 -3 -1 173.68 7.20 9 -3 -1 161.98 7.70 -9 3 1 178.38 7.60 9 3 -1 167.48 7.30 9 3 -1 172.28 7.30 9 3 -1 166.48 7.40 7 -3 -1 111.39 5.00 7 3 -1 104.49 5.20 -7 3 1 91.79 5.50 7 3 -1 105.49 5.00 7 3 -1 110.39 5.00 -5 3 1 20.80 2.50 5 3 -1 23.70 1.90 5 3 -1 17.50 2.40 5 3 -1 19.60 2.30 3 -3 -1 364.86 13.60 3 3 -1 347.07 13.60 3 3 -1 358.96 13.80 -3 3 1 356.26 13.90 1 -3 -1 12.90 3.90 1 3 -1 21.60 2.50 -1 3 1 19.10 2.80 1 3 -1 21.70 2.50 -1 3 1 22.20 2.50 1 -3 1 631.44 25.60 1 -3 1 678.93 24.80 -1 3 -1 704.13 25.10 -1 3 -1 728.73 26.10 1 3 1 659.63 24.90 1 3 1 685.23 25.10 3 -3 1 1083.99 40.30 3 3 1 1138.89 40.40 -3 3 -1 1138.79 40.70 3 3 1 1147.29 40.60 3 3 1 1134.79 40.50 5 -3 1 211.48 8.70 5 3 1 212.78 8.90 5 3 1 210.48 8.60 -5 3 -1 219.18 9.00 5 3 1 207.88 8.70 7 -3 1 58.39 3.30 7 -3 1 46.90 4.40 7 3 1 60.49 3.40 7 3 1 58.69 3.30 7 3 1 59.49 3.90 9 -3 1 24.70 2.40 9 -3 1 23.60 3.00 -9 3 -1 24.50 3.00 9 3 1 20.40 2.70 9 3 1 24.20 2.40 11 -3 1 21.10 2.10 11 -3 1 27.10 2.60 11 3 1 23.40 2.30 11 3 1 25.00 2.30 13 -3 1 148.89 6.50 13 -3 1 159.58 6.40 13 3 1 148.69 6.60 12 4 -1 18.60 1.60 10 -4 -1 126.19 6.10 10 4 -1 140.59 5.80 -10 4 1 145.69 6.00 8 -4 -1 16.10 1.80 8 4 -1 22.40 2.00 -8 4 1 19.90 2.20 6 -4 -1 33.10 2.50 6 4 -1 36.20 2.80 6 4 -1 36.70 2.60 -6 4 1 35.70 2.80 4 -4 -1 133.19 6.10 4 4 -1 131.69 6.10 4 4 -1 134.69 6.20 -4 4 1 135.49 6.30 -2 -4 1 18.00 2.10 2 -4 -1 20.80 2.90 -2 4 1 17.10 2.30 2 4 -1 17.90 2.20 2 4 -1 19.50 2.30 -2 4 1 19.90 2.40 0 -4 1 147.79 6.80 0 -4 -1 154.68 6.90 0 4 -1 152.18 7.00 0 4 -1 151.18 6.70 0 4 1 153.88 6.70 0 4 1 153.88 6.90 2 -4 1 1.40 1.10 2 4 1 -0.60 0.90 -2 4 -1 -1.70 1.30 -2 4 -1 2.10 1.00 2 4 1 -0.10 1.10 4 -4 1 18.50 2.00 4 4 1 14.60 2.00 -4 4 -1 18.40 2.20 4 4 1 15.90 2.20 6 -4 1 383.36 15.60 6 4 1 408.96 15.50 -6 4 -1 409.66 15.70 6 4 1 412.56 15.40 8 -4 1 181.48 7.90 8 4 1 203.28 8.00 8 4 1 192.58 8.00 10 -4 1 72.19 4.50 10 4 1 74.39 3.60 -10 4 -1 86.69 4.10 -9 5 1 1.40 1.20 9 5 -1 3.90 0.90 -7 -5 1 9.70 2.50 7 -5 -1 10.00 1.60 -7 5 1 14.00 1.40 7 5 -1 16.00 1.30 7 5 -1 10.80 1.60 5 -5 -1 49.90 2.80 -5 -5 1 51.69 2.90 5 5 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4802.82 166.88 -2 0 2 2068.79 71.89 0 0 -2 1.40 0.20 0 0 2 1.30 0.20 -2 0 -2 218.78 7.50 2 0 2 198.48 7.50 4 0 2 2799.42 97.59 6 0 2 7545.44 272.57 6 0 2 8134.99 272.57 8 0 2 4415.26 148.39 -8 0 -2 4090.19 148.39 10 0 2 879.61 32.00 10 0 2 876.11 31.50 10 0 2 872.51 31.80 12 0 2 114.29 5.20 12 0 2 120.59 5.50 12 0 2 105.19 5.60 14 0 2 872.91 32.60 14 0 2 918.91 33.00 14 0 2 911.31 33.00 16 0 2 1.20 0.70 16 0 2 -0.70 0.90 18 0 2 66.69 2.90 17 -1 -2 126.09 5.50 17 -1 -2 119.89 5.40 17 1 -2 119.29 5.00 15 -1 -2 293.87 11.60 15 -1 -2 290.77 11.90 15 1 -2 290.17 11.70 13 -1 -2 727.13 26.30 13 -1 -2 718.13 27.00 13 -1 -2 717.33 26.70 13 1 -2 720.13 26.70 13 1 -2 724.43 26.50 11 -1 -2 522.85 19.90 11 -1 -2 513.35 20.10 11 -1 -2 538.85 19.50 11 1 -2 534.05 19.80 11 1 -2 525.35 20.10 11 1 -2 545.35 19.60 -9 -1 2 55.69 4.30 9 -1 -2 59.59 3.90 9 -1 -2 61.59 3.10 9 -1 -2 61.59 3.60 9 1 -2 61.29 3.20 -7 -1 2 81.69 3.90 -7 -1 2 73.99 4.30 7 -1 -2 68.29 3.30 7 1 -2 73.39 3.40 -5 -1 2 1377.56 49.20 -5 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3137.59 108.29 1 -1 10 3248.97 109.19 1 1 10 3100.29 108.29 -1 1 -10 2961.30 109.29 1 1 10 3055.19 109.09 3 -1 10 2160.18 74.49 3 -1 10 2060.49 75.09 3 1 10 2154.68 74.49 3 1 10 2112.29 75.49 5 -1 10 -3.20 2.20 5 -1 10 1.00 0.80 5 1 10 0.80 1.20 5 1 10 1.60 0.70 7 -1 10 268.67 10.10 7 -1 10 255.47 10.50 7 -1 10 249.68 10.20 7 1 10 250.27 10.20 7 1 10 241.58 10.10 9 -1 10 752.72 29.20 9 -1 10 779.22 29.00 9 -1 10 820.12 29.00 9 1 10 828.72 29.00 9 1 10 775.12 28.90 11 -1 10 136.99 6.40 11 -1 10 148.19 6.40 11 1 10 138.99 6.60 11 1 10 151.98 6.40 13 -1 10 191.78 7.80 13 -1 10 179.38 7.60 13 1 10 186.88 7.80 13 1 10 187.68 7.60 15 -1 10 45.50 2.40 16 -2 -10 84.09 3.80 16 -2 -10 80.19 3.80 -16 2 10 76.09 3.70 16 2 -10 77.39 3.70 14 -2 -10 10.40 2.80 14 -2 -10 12.30 2.00 14 2 -10 11.20 1.80 14 2 -10 12.90 3.00 14 2 -10 13.80 2.00 12 -2 -10 52.19 3.30 12 -2 -10 48.60 3.50 12 2 -10 48.30 3.20 12 2 -10 47.90 3.70 12 2 -10 49.70 3.10 10 -2 -10 16.60 2.80 10 -2 -10 16.00 2.50 10 2 -10 18.10 2.20 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1.40 12 2 -22 7.50 1.60 10 -2 -22 105.99 4.80 -10 2 22 102.89 4.60 10 2 -22 106.09 4.60 10 2 -22 104.99 4.80 10 2 -22 104.69 4.50 -10 2 22 97.69 4.60 8 -2 -22 5.80 1.40 -8 2 22 2.60 1.40 8 2 -22 5.20 1.70 8 2 -22 2.00 1.00 -8 2 22 1.00 0.80 8 2 -22 1.10 0.70 6 -2 -22 312.17 12.20 6 2 -22 314.47 11.90 6 2 -22 306.17 12.40 -6 2 22 309.87 12.20 4 -2 -22 216.08 9.20 -4 2 22 235.28 9.20 4 2 -22 219.68 9.40 2 -2 -22 171.28 7.40 2 2 -22 171.48 7.60 -2 2 22 169.68 7.20 0 -2 -22 317.37 12.60 0 2 22 328.97 12.40 0 2 -22 319.07 12.80 -2 -2 -22 23.60 2.00 -2 2 -22 23.50 2.00 -4 -2 -22 11.80 1.50 -4 2 -22 10.40 1.50 -6 -2 -22 62.99 2.90 -6 2 -22 60.59 3.00 9 -3 -22 38.90 2.20 -9 3 22 37.80 2.10 9 3 -22 37.30 2.20 7 -3 -22 1.60 0.90 7 3 -22 2.10 1.20 -7 3 22 0.60 0.70 5 -3 -22 10.70 1.70 5 3 -22 10.00 1.60 -5 3 22 9.60 1.30 3 -3 -22 75.09 3.60 3 3 -22 68.79 3.60 -3 3 22 77.09 3.60 1 -3 -22 196.68 7.40 1 3 -22 178.38 7.40 -1 3 22 179.18 7.30 -1 3 -22 22.40 2.00 1 3 22 20.50 1.80 -3 3 -22 283.37 10.60 14 0 -23 0.60 0.70 -14 0 23 2.30 0.80 12 0 -23 -0.60 0.80 12 0 -23 -0.10 0.90 -12 0 23 0.00 0.70 12 0 -23 0.20 0.80 10 0 -23 -0.40 0.90 10 0 -23 0.20 0.90 10 0 -23 -0.40 1.00 8 0 -23 -0.10 1.10 8 0 -23 0.70 1.50 8 0 -23 1.70 0.90 6 0 -23 9.50 2.10 4 0 -23 0.20 1.10 4 0 -23 -0.40 1.00 -4 0 23 -1.20 1.00 2 0 -23 1.30 1.20 -2 0 23 -0.20 1.70 2 0 -23 4.10 1.20 0 0 -23 -0.90 1.20 -2 0 -23 -1.40 1.20 -2 0 -23 0.20 0.90 -4 0 -23 0.40 0.80 -4 0 -23 -0.30 1.20 -6 0 -23 -0.40 0.70 13 -1 -23 70.69 3.50 13 -1 -23 75.89 3.40 13 1 -23 80.29 3.90 -13 1 23 78.09 3.40 11 -1 -23 2.00 1.00 11 -1 -23 0.90 0.70 11 1 -23 1.10 0.80 11 1 -23 -0.50 0.80 -11 1 23 1.20 0.70 9 -1 -23 264.47 10.50 9 -1 -23 258.77 10.60 -9 1 23 264.87 10.50 9 1 -23 269.77 10.30 9 1 -23 265.87 10.80 7 -1 -23 117.09 5.60 7 -1 -23 119.79 5.60 -7 1 23 122.39 5.50 7 1 -23 110.39 5.70 5 -1 -23 8.20 2.70 5 1 -23 5.80 1.50 3 -1 -23 24.10 2.40 3 1 -23 18.30 2.60 3 1 -23 23.70 2.60 -3 1 23 19.80 2.60 1 -1 -23 170.38 9.30 1 1 -23 163.48 7.00 1 1 -23 153.58 8.30 -1 1 23 163.88 6.90 -1 -1 -23 13.10 1.80 -1 1 -23 11.10 1.80 -1 1 -23 13.50 2.10 -3 -1 -23 125.49 5.50 -3 1 -23 120.79 5.60 -3 1 -23 123.59 5.30 -5 -1 -23 107.49 4.70 -5 1 -23 106.59 4.70 -5 1 -23 106.29 4.60 -7 -1 -23 193.68 7.30 -7 1 -23 191.38 8.30 12 -2 -23 0.70 0.50 12 2 -23 -0.70 0.70 -12 2 23 -1.10 1.20 -12 2 23 -1.30 0.80 12 2 -23 1.20 0.80 10 -2 -23 167.18 6.90 10 2 -23 165.78 6.90 -10 2 23 164.08 6.70 -10 2 23 165.68 6.80 10 2 -23 189.48 7.20 8 -2 -23 167.18 7.00 8 2 -23 167.98 6.90 -8 2 23 169.18 7.00 8 2 -23 175.78 7.20 6 -2 -23 2.90 0.90 -6 2 23 2.40 0.80 6 2 -23 1.40 0.80 4 -2 -23 41.40 2.70 4 2 -23 43.10 3.10 -4 2 23 38.90 2.60 2 -2 -23 24.10 2.00 2 2 -23 23.50 2.60 -2 2 23 23.40 2.00 0 -2 -23 200.38 8.40 0 2 -23 210.98 8.70 0 2 23 208.98 8.20 -2 -2 -23 245.68 9.10 -2 2 -23 207.98 9.40 -4 -2 -23 2.30 0.70 -4 2 -23 1.70 0.70 -9 3 23 72.69 3.10 7 -3 -23 91.99 4.00 -7 3 23 91.39 4.00 7 3 -23 100.79 5.00 5 -3 -23 1.50 1.00 5 3 -23 -1.10 1.00 -5 3 23 1.40 0.60 3 -3 -23 12.30 1.80 -3 3 23 8.80 1.20 3 3 -23 10.00 1.50 1 -3 -23 4.60 1.30 1 3 -23 5.00 1.40 -1 3 -23 1.50 0.80 12 0 -24 5.50 1.50 12 0 -24 3.10 0.80 -12 0 24 4.80 1.10 10 0 -24 34.60 2.40 10 0 -24 34.80 2.40 10 0 -24 35.10 2.40 -10 0 24 36.00 2.30 8 0 -24 837.72 30.90 8 0 -24 858.71 30.70 6 0 -24 478.55 18.90 -6 0 24 514.15 18.70 6 0 -24 506.75 18.70 4 0 -24 63.89 3.70 -4 0 24 54.69 3.20 4 0 -24 58.09 3.40 2 0 -24 3.80 1.10 -2 0 24 3.10 1.20 2 0 -24 2.50 1.00 0 0 -24 150.58 6.70 0 0 -24 150.18 6.60 -2 0 -24 212.58 8.70 -2 0 -24 218.28 8.70 -4 0 -24 7.90 2.70 -4 0 -24 5.00 1.30 -6 0 -24 198.38 7.60 13 -1 -24 0.50 0.60 -13 -1 24 0.20 0.60 13 1 -24 -0.80 0.80 13 1 -24 -0.20 0.60 -13 1 24 0.40 1.50 -13 1 24 0.40 0.80 11 -1 -24 0.80 0.60 11 -1 -24 0.80 1.00 -11 1 24 1.20 0.70 11 1 -24 2.70 1.50 11 1 -24 1.90 0.70 9 -1 -24 248.08 9.70 9 -1 -24 231.48 9.60 9 1 -24 244.48 9.50 9 1 -24 252.57 9.90 -9 1 24 247.38 9.70 7 -1 -24 297.07 12.20 7 -1 -24 316.57 19.40 7 1 -24 323.17 12.90 -7 1 24 310.57 12.10 5 -1 -24 163.38 7.20 5 -1 -24 155.68 7.00 5 1 -24 156.68 7.20 -5 1 24 168.08 6.90 5 1 -24 161.88 7.20 3 -1 -24 29.70 2.30 -3 -1 24 31.00 2.60 -3 1 24 27.80 2.30 3 1 -24 31.10 2.50 3 1 -24 26.40 2.60 1 -1 -24 2.30 0.90 1 1 -24 1.60 0.90 1 1 -24 0.20 1.30 -1 1 24 1.00 1.20 -1 -1 -24 628.14 23.60 -1 1 -24 640.74 23.30 -1 1 -24 659.53 23.80 -3 -1 -24 34.50 2.40 -3 1 -24 34.00 2.50 -3 1 -24 34.80 2.30 -5 -1 -24 551.64 20.00 -5 1 -24 546.15 19.90 10 2 -24 19.90 1.60 10 2 -24 18.80 2.00 -10 2 24 22.30 1.60 8 -2 -24 22.60 1.70 -8 2 24 25.70 1.80 8 2 -24 24.00 1.90 6 -2 -24 10.20 1.40 -6 2 24 10.10 1.40 6 2 -24 12.30 1.60 4 -2 -24 324.27 12.20 4 2 -24 298.37 12.10 -4 2 24 307.07 11.80 2 -2 -24 183.38 7.60 -2 2 24 160.48 6.80 2 2 -24 162.78 7.10 0 -2 -24 23.20 1.80 0 2 24 18.90 2.10 0 2 -24 27.30 2.20 -2 -2 -24 31.60 2.00 -2 2 -24 30.70 2.00 -4 -2 -24 47.40 2.30 -4 2 -24 41.80 2.30 -5 3 24 3.30 1.00 -3 3 24 33.50 1.80 3 3 -24 31.30 2.00 1 3 -24 17.40 1.60 -12 0 25 -0.50 0.60 12 0 -25 -0.40 0.70 -10 0 25 -0.40 0.60 10 0 -25 0.30 0.80 10 0 -25 0.00 0.90 8 0 -25 -0.80 0.90 -8 0 25 0.20 0.70 8 0 -25 1.50 0.90 -6 0 25 -0.20 0.80 6 0 -25 -0.20 1.00 6 0 -25 0.30 1.00 -4 0 25 -0.50 0.90 4 0 -25 -0.10 0.90 4 0 -25 1.00 1.00 2 0 -25 0.20 1.00 2 0 -25 0.70 0.90 0 0 -25 1.40 1.10 0 0 -25 0.80 0.80 -2 0 -25 0.50 0.80 -2 0 -25 0.70 1.30 -4 0 -25 -0.70 0.70 11 -1 -25 48.80 2.40 11 1 -25 42.10 2.80 11 1 -25 46.80 2.90 -11 1 25 49.00 2.50 9 -1 -25 101.29 4.70 9 -1 -25 103.99 4.60 -9 1 25 103.09 4.60 9 1 -25 106.09 4.80 7 -1 -25 272.87 10.90 7 -1 -25 281.87 11.20 7 1 -25 274.27 10.90 -7 1 25 268.87 10.70 5 -1 -25 8.40 1.50 -5 -1 25 11.70 1.80 5 1 -25 11.20 1.80 -5 1 25 9.30 1.50 3 -1 -25 261.77 10.50 -3 1 25 265.57 10.20 3 1 -25 268.07 10.70 1 -1 -25 102.59 4.90 1 1 -25 103.59 4.80 1 1 -25 112.49 5.20 -1 -1 -25 29.50 2.00 -1 1 -25 27.60 2.10 -1 1 -25 30.80 2.40 -3 -1 -25 5.80 1.20 -3 1 -25 7.50 1.30 10 -2 -25 8.00 1.10 10 2 -25 7.70 1.30 -10 2 25 9.90 1.20 8 -2 -25 90.49 3.90 -8 2 25 94.39 3.90 8 2 -25 74.09 4.10 6 -2 -25 11.00 1.40 -6 2 25 9.70 1.30 6 2 -25 11.30 1.40 4 -2 -25 4.50 1.40 -4 2 25 0.80 0.70 4 2 -25 1.70 0.80 2 -2 -25 76.49 3.50 -2 2 25 72.39 3.50 2 2 -25 76.59 3.70 0 -2 -25 71.69 3.30 0 2 -25 64.19 3.30 -2 -2 -25 -0.80 0.70 -2 2 -25 0.70 0.70 -10 0 26 118.69 4.80 10 0 -26 111.69 4.80 10 0 -26 114.49 4.70 8 0 -26 451.55 16.50 -8 0 26 454.85 16.80 8 0 -26 442.96 16.70 6 0 -26 346.67 12.80 6 0 -26 334.97 12.90 -6 0 26 330.97 12.70 4 0 -26 41.40 2.50 -4 0 26 42.50 2.50 4 0 -26 41.90 2.60 2 0 -26 47.50 2.90 2 0 -26 45.10 2.60 0 0 -26 13.10 2.00 0 0 -26 12.70 1.50 -2 0 -26 427.06 15.60 -4 0 -26 162.38 6.20 11 -1 -26 34.80 2.00 -11 -1 26 34.20 1.90 -11 1 26 39.00 1.90 11 1 -26 38.50 2.00 -9 -1 26 16.10 1.60 9 -1 -26 18.70 1.60 9 1 -26 19.70 1.60 -9 1 26 16.80 1.40 7 -1 -26 32.60 2.30 -7 -1 26 36.20 2.10 7 1 -26 35.10 2.20 -7 1 26 33.10 2.10 -5 -1 26 45.90 2.70 5 -1 -26 48.80 2.70 -5 1 26 52.29 2.70 5 1 -26 50.99 2.90 3 -1 -26 130.39 5.60 -3 1 26 126.09 5.30 3 1 -26 130.19 5.70 1 -1 -26 80.89 3.80 1 1 -26 79.09 3.80 -1 -1 -26 60.09 3.00 -1 1 -26 67.49 3.30 -3 -1 -26 396.76 13.60 -3 1 -26 343.97 13.40 8 -2 -26 63.19 2.70 -8 2 26 56.59 2.60 8 2 -26 53.29 2.70 6 -2 -26 4.50 1.10 6 2 -26 3.30 1.20 -6 2 26 5.10 1.10 4 -2 -26 18.90 1.50 -4 2 26 20.30 1.60 4 2 -26 17.00 1.60 2 -2 -26 23.80 1.60 2 2 -26 20.60 1.60 0 -2 -26 1.00 0.70 0 2 -26 0.90 0.60 10 0 -27 -1.40 0.90 -10 0 27 0.70 0.60 8 0 -27 1.60 0.90 -8 0 27 0.80 0.70 8 0 -27 1.60 1.00 -6 0 27 1.90 0.90 6 0 -27 -0.20 0.80 6 0 -27 0.90 1.10 4 0 -27 0.10 0.90 -4 0 27 -1.00 1.20 4 0 -27 -1.20 1.10 2 0 -27 -2.00 1.10 0 0 -27 -0.20 0.70 -2 0 -27 -0.20 0.80 -9 -1 27 0.50 0.70 9 -1 -27 -0.40 0.60 -9 1 27 -0.90 0.50 9 1 -27 -0.90 0.70 -7 -1 27 15.90 1.60 7 -1 -27 16.30 1.40 -7 1 27 12.70 1.40 7 1 -27 15.10 1.50 5 -1 -27 233.98 9.10 5 1 -27 242.48 9.20 -5 1 27 233.98 8.90 3 -1 -27 85.49 3.80 3 1 -27 84.69 3.90 -3 1 27 82.89 3.90 1 -1 -27 100.59 4.30 1 1 -27 102.59 4.40 -1 -1 -27 105.19 4.30 -1 1 -27 101.39 4.30 4 -2 -27 43.90 2.20 4 2 -27 41.90 2.20 -8 0 28 365.16 13.20 -6 0 28 103.59 4.30 6 0 -28 101.19 4.50 6 0 -28 100.69 4.40 4 0 -28 338.97 12.40 2 0 -28 353.96 12.90 7 -1 -28 26.10 1.60 -7 1 28 23.40 1.60 7 1 -28 25.30 1.60 5 -1 -28 126.49 5.00 5 1 -28 123.49 5.10 3 -1 -28 3.70 1.10 3 1 -28 2.10 0.80 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 24341 _shelx_res_file ; TITL JTM1239_0m_a.res in C2/c JTM1239_0m_a.res created by SHELXL-2018/3 at 14:20:48 on 15-Jan-2020 REM Old TITL JTM1239_0m in C2/c REM SHELXT solution in C2/c REM R1 0.155, Rweak 0.002, Alpha 0.018, Orientation as input REM Formula found by SHELXT: C8 N3 O3 CELL 1.54178 15.3747 4.6699 23.0423 90.000 103.122 90.000 ZERR 8.000 0.0004 0.0001 0.0005 0.000 0.001 0.000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H N O UNIT 56 48 32 24 TEMP 23 SIZE 0.11 0.176 0.236 L.S. 5 BOND $H LIST 4 CONF EQIV $1 -x+1, -y+1, -z+1 HTAB N1 O1_$1 EQIV $2 -x+1/2, y+1/2, -z+1/2 HTAB O2 N2_$2 EQIV $3 -x+1/2, -y+3/2, -z+1 HTAB C5 O1_$3 EQIV $4 -x, y, -z+1/2 HTAB C6 O3_$4 ACTA 136 FMAP 2 PLAN 5 MPLA N1 > C5 MPLA C6 C7 O2 O3 WGHT 0.063000 0.626500 EXTI 0.030376 FVAR 0.98285 O1 4 0.393511 0.612607 0.495221 11.00000 0.04779 0.05929 = 0.04402 -0.01978 0.00212 -0.00208 AFIX 3 H1 2 0.491406 0.298878 0.457379 11.00000 -1.50000 AFIX 0 O2 4 0.178450 0.301057 0.249161 11.00000 0.05621 0.04840 = 0.03373 0.00656 0.00241 -0.00943 AFIX 3 H2A 2 0.169736 0.370596 0.213269 11.00000 -1.50000 AFIX 0 O3 4 0.079058 -0.027431 0.206123 11.00000 0.05373 0.07867 = 0.03698 -0.00753 -0.00303 -0.01454 N1 3 0.434397 0.265805 0.436842 11.00000 0.03774 0.04869 = 0.03617 -0.00629 0.00310 -0.00224 N2 3 0.335832 0.001334 0.363090 11.00000 0.04087 0.04352 = 0.03331 -0.00575 0.00568 -0.00113 N3 3 0.181903 0.119814 0.359666 11.00000 0.03725 0.04338 = 0.02999 -0.00023 0.00401 -0.00258 C1 1 0.370529 0.429027 0.456395 11.00000 0.04345 0.04247 = 0.02931 -0.00362 0.00501 -0.00213 C2 1 0.415822 0.069359 0.392701 11.00000 0.04183 0.04699 = 0.03658 -0.00511 0.00694 0.00064 AFIX 43 H2 2 0.463751 -0.024383 0.382697 11.00000 -1.20000 AFIX 0 C3 1 0.270307 0.148898 0.381527 11.00000 0.03798 0.03920 = 0.02783 0.00157 0.00563 -0.00206 C4 1 0.281991 0.356060 0.425769 11.00000 0.04047 0.04251 = 0.02896 -0.00193 0.00620 -0.00131 N4 3 0.134698 0.303963 0.387343 11.00000 0.04154 0.05247 = 0.03643 -0.00014 0.00867 0.00208 C5 1 0.194811 0.443802 0.427170 11.00000 0.04523 0.05102 = 0.03480 -0.00501 0.00814 0.00263 AFIX 43 H5 2 0.181431 0.582221 0.452827 11.00000 -1.20000 AFIX 0 C6 1 0.136000 -0.056941 0.310649 11.00000 0.04179 0.04326 = 0.03480 -0.00031 0.00181 -0.00925 AFIX 23 H6A 2 0.076673 -0.099206 0.316240 11.00000 -1.20000 H6B 2 0.167753 -0.237123 0.311870 11.00000 -1.20000 AFIX 0 C7 1 0.127306 0.075738 0.249551 11.00000 0.03545 0.04455 = 0.03362 -0.00180 0.00238 0.00041 HKLF 4 REM JTM1239_0m_a.res in C2/c REM wR2 = 0.114340, GooF = S = 1.15490, Restrained GooF = 1.15490 for all data REM R1 = 0.047552 for 1503 Fo > 4sig(Fo) and 0.049017 for all 1598 data REM 128 parameters refined using 0 restraints END WGHT 0.0630 0.6259 REM Highest difference peak 0.248, deepest hole -0.329, 1-sigma level 0.087 Q1 1 0.3742 0.9085 0.4850 11.00000 0.05 0.24 Q2 1 0.0752 -0.2155 0.3804 11.00000 0.05 0.22 Q3 1 0.4211 0.4193 0.5663 11.00000 0.05 0.22 Q4 1 0.5036 0.0598 0.3721 11.00000 0.05 0.21 Q5 1 0.5551 0.4356 0.3994 11.00000 0.05 0.21 ; _shelx_res_checksum 51145 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 0.39351(7) 0.6126(2) 0.49522(5) 0.0517(4) Uani d 1 . . H H1 0.491406 0.298878 0.457379 0.078 Uiso d 1 . . O O2 0.17845(7) 0.3011(2) 0.24916(4) 0.0474(3) Uani d 1 . . H H2A 0.169736 0.370596 0.213269 0.071 Uiso d 1 . . O O3 0.07906(7) -0.0274(3) 0.20612(5) 0.0586(4) Uani d 1 . . N N1 0.43440(7) 0.2658(3) 0.43684(5) 0.0417(3) Uani d 1 . . N N2 0.33583(7) 0.0013(3) 0.36309(5) 0.0397(3) Uani d 1 . . N N3 0.18190(7) 0.1198(3) 0.35967(5) 0.0375(3) Uani d 1 . . C C1 0.37053(9) 0.4290(3) 0.45639(6) 0.0389(4) Uani d 1 . . C C2 0.41582(9) 0.0694(3) 0.39270(6) 0.0421(4) Uani d 1 . . H H2 0.463751 -0.024383 0.382697 0.051 Uiso calc 1 . . C C3 0.27031(9) 0.1489(3) 0.38153(5) 0.0353(3) Uani d 1 . . C C4 0.28199(9) 0.3561(3) 0.42577(5) 0.0376(3) Uani d 1 . . N N4 0.13470(8) 0.3040(3) 0.38734(5) 0.0435(3) Uani d 1 . . C C5 0.19481(10) 0.4438(3) 0.42717(6) 0.0438(4) Uani d 1 . . H H5 0.181431 0.582221 0.452827 0.053 Uiso calc 1 . . C C6 0.13600(9) -0.0569(3) 0.31065(6) 0.0410(4) Uani d 1 . . H H6A 0.076673 -0.099206 0.316240 0.049 Uiso calc 1 . . H H6B 0.167753 -0.237123 0.311870 0.049 Uiso calc 1 . . C C7 0.12731(8) 0.0757(3) 0.24955(6) 0.0387(4) 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 0.0478(6) 0.0593(7) 0.0440(6) -0.0021(5) 0.0021(4) -0.0198(5) O2 0.0562(6) 0.0484(6) 0.0337(5) -0.0094(5) 0.0024(4) 0.0066(4) O3 0.0537(7) 0.0787(8) 0.0370(6) -0.0145(6) -0.0030(5) -0.0075(5) N1 0.0377(6) 0.0487(7) 0.0362(6) -0.0022(5) 0.0031(5) -0.0063(5) N2 0.0409(6) 0.0435(6) 0.0333(6) -0.0011(5) 0.0057(5) -0.0058(5) N3 0.0373(6) 0.0434(6) 0.0300(6) -0.0026(5) 0.0040(4) -0.0002(4) C1 0.0435(7) 0.0425(7) 0.0293(6) -0.0021(6) 0.0050(5) -0.0036(5) C2 0.0418(7) 0.0470(8) 0.0366(7) 0.0006(6) 0.0069(6) -0.0051(6) C3 0.0380(7) 0.0392(7) 0.0278(6) -0.0021(5) 0.0056(5) 0.0016(5) C4 0.0405(7) 0.0425(7) 0.0290(6) -0.0013(5) 0.0062(5) -0.0019(5) N4 0.0415(6) 0.0525(7) 0.0364(6) 0.0021(5) 0.0087(5) -0.0001(5) C5 0.0452(8) 0.0510(8) 0.0348(7) 0.0026(6) 0.0081(6) -0.0050(6) C6 0.0418(7) 0.0433(8) 0.0348(7) -0.0092(6) 0.0018(5) -0.0003(5) C7 0.0354(7) 0.0446(8) 0.0336(7) 0.0004(5) 0.0024(5) -0.0018(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O2 H2A . . 110.0 ? C2 N1 C1 . . 124.73(11) ? C2 N1 H1 . . 121.4 ? C1 N1 H1 . . 113.9 ? C2 N2 C3 . . 112.91(12) ? C3 N3 N4 . . 111.03(11) ? C3 N3 C6 . . 128.49(12) ? N4 N3 C6 . . 120.31(11) ? O1 C1 N1 . . 120.51(13) ? O1 C1 C4 . . 127.62(13) ? N1 C1 C4 . . 111.86(11) ? N2 C2 N1 . . 124.94(13) ? N2 C2 H2 . . 117.5 ? N1 C2 H2 . . 117.5 ? N3 C3 N2 . . 125.93(12) ? N3 C3 C4 . . 107.27(12) ? N2 C3 C4 . . 126.80(12) ? C3 C4 C5 . . 104.74(12) ? C3 C4 C1 . . 118.71(12) ? C5 C4 C1 . . 136.54(13) ? C5 N4 N3 . . 105.83(11) ? N4 C5 C4 . . 111.12(13) ? N4 C5 H5 . . 124.4 ? C4 C5 H5 . . 124.4 ? N3 C6 C7 . . 114.60(11) ? N3 C6 H6A . . 108.6 ? C7 C6 H6A . . 108.6 ? N3 C6 H6B . . 108.6 ? C7 C6 H6B . . 108.6 ? H6A C6 H6B . . 107.6 ? O3 C7 O2 . . 124.87(13) ? O3 C7 C6 . . 121.10(13) ? O2 C7 C6 . . 113.99(11) ? 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 C1 . 1.2315(17) ? O2 C7 . 1.3148(17) ? O2 H2A . 0.8701 ? O3 C7 . 1.2028(17) ? N1 C2 . 1.3512(18) ? N1 C1 . 1.3961(18) ? N1 H1 . 0.9098 ? N2 C2 . 1.3030(18) ? N2 C3 . 1.3655(17) ? N3 C3 . 1.3449(17) ? N3 N4 . 1.3723(16) ? N3 C6 . 1.4468(17) ? C1 C4 . 1.4251(18) ? C2 H2 . 0.9300 ? C3 C4 . 1.3872(19) ? C4 C5 . 1.4090(19) ? N4 C5 . 1.3182(19) ? C5 H5 . 0.9300 ? C6 C7 . 1.5160(18) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? 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 O1 5_666 0.91 1.90 2.8094(16) 175 yes O2 H2A N2 4 0.87 1.85 2.7120(14) 173 yes C5 H5 O1 7_566 0.93 2.33 3.2305(18) 164 yes C6 H6A O3 2 0.97 2.36 3.2436(18) 152 yes C6 H6B Cg1 1_545 0.97 2.98 3.7387(15) 136 y 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 C2 N1 C1 O1 . . . . -176.82(13) ? C2 N1 C1 C4 . . . . 2.4(2) ? C3 N2 C2 N1 . . . . -0.6(2) ? C1 N1 C2 N2 . . . . -1.4(2) ? N4 N3 C3 N2 . . . . -178.88(12) ? C6 N3 C3 N2 . . . . -3.7(2) ? N4 N3 C3 C4 . . . . 0.92(15) ? C6 N3 C3 C4 . . . . 176.06(12) ? C2 N2 C3 N3 . . . . -179.00(13) ? C2 N2 C3 C4 . . . . 1.2(2) ? N3 C3 C4 C5 . . . . -0.49(15) ? N2 C3 C4 C5 . . . . 179.30(13) ? N3 C3 C4 C1 . . . . -179.86(11) ? N2 C3 C4 C1 . . . . -0.1(2) ? O1 C1 C4 C3 . . . . 177.49(14) ? N1 C1 C4 C3 . . . . -1.64(18) ? O1 C1 C4 C5 . . . . -1.6(3) ? N1 C1 C4 C5 . . . . 179.24(15) ? C3 N3 N4 C5 . . . . -0.97(15) ? C6 N3 N4 C5 . . . . -176.57(12) ? N3 N4 C5 C4 . . . . 0.64(16) ? C3 C4 C5 N4 . . . . -0.10(16) ? C1 C4 C5 N4 . . . . 179.09(15) ? C3 N3 C6 C7 . . . . -83.22(17) ? N4 N3 C6 C7 . . . . 91.53(15) ? N3 C6 C7 O3 . . . . -168.31(14) ? N3 C6 C7 O2 . . . . 13.70(18) ? _cod_database_fobs_code 2244154