#------------------------------------------------------------------------------ #$Date: 2021-09-06 13:23:59 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268648 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243257.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7243257 loop_ _publ_author_name 'Yamaguchi, Ryota' 'Tanaka, Rika' 'Maetani, Mayu' 'Tabe, Hiroyasu' 'Yamada, Yusuke' _publ_section_title ; Efficient capturing of hydrogen peroxide in dilute aqueous solution by co-crystallization with amino acids ; _journal_issue 32 _journal_name_full CrystEngComm _journal_page_first 5456 _journal_page_last 5462 _journal_paper_doi 10.1039/D1CE00688F _journal_volume 23 _journal_year 2021 _chemical_absolute_configuration rm _chemical_formula_moiety 'C9 H11 N O2, H2 O2, 0.5(H2 O)' _chemical_formula_sum 'C9 H14 N O4.5' _chemical_formula_weight 208.21 _chemical_name_systematic L-Phe.H2O2.0.5H2O _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _audit_block_doi 10.5517/ccdc.csd.cc27y8l2 _audit_creation_date 2019-2-8 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-14 deposited with the CCDC. 2021-07-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.803(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9671(3) _cell_length_b 7.2000(3) _cell_length_c 14.1385(6) _cell_measurement_reflns_used 4601 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.8330 _cell_measurement_theta_min 3.4480 _cell_volume 1013.41(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 7.32 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; scan: Number of images: 600 Slice: -80.0000 - 100.000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Phi Omega: 0.0000 Chi: 0.0000 Phi: 0.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 0.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 90.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 180.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 270.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 195 Slice: -15.0000 - 43.5000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 195 Slice: -15.0000 - 43.5000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 195 Slice: -15.0000 - 43.5000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 180.0000 XTD: 54.1393 2theta: 25.8615 scan: Number of images: 195 Slice: -15.0000 - 43.5000 Image width: 0.3000 Exp time: 24.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 270.0000 XTD: 54.1393 2theta: 25.8615 ; _diffrn_measurement_device 'Mercury CCD (2x2 bin mode)' _diffrn_measurement_device_details 'AFC7: Eulerian 3-circle' _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method '\w and \f' _diffrn_radiation_detector CCD _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.1170 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 6166 _diffrn_reflns_point_group_measured_fraction_full 0.805 _diffrn_reflns_point_group_measured_fraction_max 0.787 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.477 _diffrn_reflns_theta_min 2.885 _diffrn_source_current 200.0000 _diffrn_source_power 10.0000 _diffrn_source_voltage 50.0000 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Platelet _exptl_crystal_F_000 444 _exptl_crystal_preparation 'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 150(2) K' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.4000 _exptl_crystal_size_mid 0.3600 _exptl_crystal_size_min 0.0200 _refine_diff_density_max 0.355 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details ; Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -1.2(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 1819 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.095 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0505 _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^)+(0.0877P)^2^+0.5312P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1285 _refine_ls_wR_factor_ref 0.1325 _reflns_Friedel_coverage 0.461 _reflns_Friedel_fraction_full 0.575 _reflns_Friedel_fraction_max 0.540 _reflns_number_gt 1738 _reflns_number_total 1819 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ce00688f2.cif _cod_data_source_block L-PhenylAlanine_H2O2 _cod_depositor_comments 'Adding full bibliography for 7243257--7243260.cif.' _cod_original_sg_symbol_H-M 'C 2' _cod_database_code 7243257 _shelx_shelxl_version_number 2018/3 _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 2 -17 23.0819 16.9731 0 3 3 -13 163.668 14.7103 0 4 4 -13 484.181 18.8306 0 -5 -1 -9 33.2592 8.03640 0 3 3 -14 100.798 14.1380 0 0 0 -9 0.06249 6.88055 0 -2 2 -18 128.598 18.3433 0 5 5 -14 0.37306 14.3225 0 1 1 -13 42.2535 11.4753 0 1 3 -18 26.2876 18.1809 0 -4 0 -15 12.4044 12.7791 0 2 2 -15 85.8196 14.4706 0 4 4 -16 10.6929 15.4058 0 -2 0 -15 94.2679 13.7599 0 4 2 -11-4.57942 10.0773 0 4 4 -17-1.80383 16.6148 0 3 3 -17 49.2517 15.5815 0 6 4 -11 62.8198 11.3672 0 0 0 -13 16.5505 10.7997 0 5 3 -2 4475.44 17.6584 0 4 2 -2 1161.99 8.53253 0 -1 1 -18 88.8519 16.9718 0 -4 0 -17 76.1803 14.8767 0 1 1 -16 11.0055 12.8880 0 6 4 -13 1.50640 11.9258 0 2 2 -18-5.34668 16.3669 0 1 1 -17 0.13823 15.1118 0 5 3 -15 74.7751 15.4832 0 0 0 -16 30.9959 14.0241 0 -2 0 -18 12.5388 16.0590 0 6 4 -15 17.0966 14.7760 0 -5 -1 -16 38.3690 14.7292 0 0 0 -17 32.3016 15.8591 0 5 3 -17 71.9654 19.5589 0 3 1 -16 11.7502 15.9707 0 2 0 -14 15.0478 12.2887 0 1 -1 -13 53.8194 12.6328 0 2 0 -17 26.6700 15.3455 0 7 3 -12 77.0828 12.6875 0 5 1 -13 0.96886 11.8764 0 6 2 -14 20.0152 12.9445 0 -1 -1 -18 102.867 17.8346 0 2 0 -18 10.6278 15.6005 0 6 2 -15-4.29301 13.9614 0 1 -1 -16 47.8969 14.6136 0 4 2 -1 1315.30 6.10993 0 5 3 -1 2463.73 11.6737 0 4 0 -10 17.1291 8.90370 0 6 2 -16 68.1337 16.2304 0 4 0 -9 15.9787 8.06561 0 1 -1 -17 0.14139 14.9740 0 -6 -2 -5 19.3308 4.10923 0 6 2 -17 92.6470 17.6041 0 0 -2 -11 70.9736 10.5573 0 -2 -2 -17 30.9262 14.6316 0 -4 -2 -18 52.8176 16.7815 0 -2 -2 -18 126.571 18.5680 0 3 -1 -16 14.0070 15.6229 0 4 0 -6 33.4668 7.45130 0 -3 -3 -15 62.4288 14.6924 0 6 0 -16 112.124 17.8478 0 -1 -3 -14 65.1853 13.3694 0 2 -2 -18 8.13231 18.1102 0 -1 -3 -15 2.88924 13.5720 0 3 1 -1 5150.39 12.6815 0 -3 -3 -18 72.3338 18.8754 0 5 -1 -13 3.60607 12.6548 0 1 -3 -14 87.2897 13.9553 0 1 -3 -13 10.8493 11.4844 0 6 0 -8 1.91311 8.01726 0 1 -3 -18 23.4382 16.0826 0 4 -2 -11-7.35896 11.0592 0 -5 -3 -7 15.6289 4.65704 0 -2 -4 -15 20.1476 13.9591 0 -2 -4 -16 24.4024 15.3747 0 3 -3 -17 49.7135 18.2817 0 8 0 -15-11.5079 15.9958 0 -2 -4 -17 42.8300 17.8398 0 0 -4 -15-3.94492 13.5530 0 8 0 -12 20.3748 12.2885 0 6 -2 -16 51.7274 17.0251 0 6 -2 -15-6.16172 14.9156 0 6 -2 -14 4.75760 14.4892 0 8 0 -11 4.04052 11.4211 0 5 -3 -15 40.5134 16.4545 0 2 -4 -13 60.1324 13.9335 0 6 0 -5-5.92223 6.32508 0 4 -4 -16 28.5230 18.2525 0 1 -5 -16-5.02140 18.2842 0 1 -5 -15 68.6561 17.9302 0 -1 -5 -12 63.8701 12.9911 0 6 -2 -8 69.4051 11.5844 0 1 -5 -13 70.0565 15.2954 0 7 -1 -7 69.6127 11.1016 0 6 -4 -15 22.5516 18.8489 0 6 -4 -13-3.99543 18.0181 0 6 -4 -12 90.1657 18.3725 0 -2 -4 -6 28.8588 7.39084 0 0 -6 -15 83.0434 19.8343 0 5 -5 -14 7.44628 19.6511 0 0 -6 -13 127.434 19.1000 0 5 -5 -13 128.066 20.7528 0 2 -6 -14 45.3732 22.2477 0 10 -2 -13 33.7608 23.1448 0 0 -6 -12 97.2987 17.9893 0 2 -6 -13 9.83218 18.2665 0 1 -5 -8 25.3734 12.5690 0 10 -2 -12 44.2089 19.8996 0 9 -3 -12 57.7250 19.9975 0 4 -6 -14 117.406 22.4309 0 -2 -4 -5 30.6373 7.43572 0 8 -4 -12 33.7435 19.1369 0 4 -6 -13 112.042 22.0445 0 7 -5 -13 133.856 24.4701 0 1 -5 -7 40.0615 11.6308 0 8 -4 -11 38.0688 18.7466 0 4 -6 -12 147.835 22.2000 0 1 -7 -14 31.3812 22.0032 0 11 -3 -11 24.4351 21.2686 0 10 -4 -11 4.99121 19.5400 0 4 -6 -8 102.879 17.3662 0 -1 -7 -10 45.8779 15.5941 0 2 -6 -7 11.3233 13.9159 0 3 -7 -10 35.5043 19.1857 0 11 -3 -10 53.1392 19.8026 0 3 -7 -9 27.5346 17.7358 0 5 3 -1 2463.73 11.6737 0 5 -5 -5 95.3224 16.1297 0 0 -8 -11 12.4251 19.8209 0 2 2 0 23946.5 36.7505 0 0 -8 -10 68.7958 19.5909 0 5 -7 -8 90.1206 19.2464 0 2 -8 -9 108.091 19.9743 0 -1 -7 -7 32.5686 12.1195 0 0 -8 -9 66.3155 16.8765 0 4 -8 -8 29.9094 19.2885 0 -2 -2 -1 153.230 3.07163 0 8 -6 -6 102.083 19.3387 0 8 0 -2-0.26298 7.02985 0 11 -5 -7 103.394 22.3986 0 8 -6 -5 86.6048 18.7384 0 7 -5 -3 146.087 15.9768 0 5 -5 -2 105.180 14.6533 0 11 -5 -6 49.1883 21.8319 0 10 -4 -4 62.0357 16.5814 0 6 -8 -6 112.637 22.1538 0 8 -6 -4 276.225 22.2358 0 4 -8 -5 7.24848 18.0634 0 8 -4 -2 121.400 16.3007 0 7 -5 -2 459.161 19.8457 0 11 -5 -5 123.960 22.3092 0 4 -6 -2 866.268 23.2180 0 9 -5 -3 887.710 24.6150 0 5 -7 -3 606.627 23.0490 0 9 -3 -2 721.887 20.5459 0 10 -4 -3 91.5481 16.6690 0 3 -9 -6 61.1318 22.3761 0 8 -6 -3 437.967 21.2065 0 6 -6 -2 98.0021 16.8284 0 10 -6 -4 31.1007 19.9538 0 11 -5 -4 321.189 22.7924 0 7 -7 -3 40.2404 17.6140 0 11 -3 -3 570.167 21.3048 0 9 -7 -4 83.7179 20.5366 0 3 -7 -2 92.5161 15.3826 0 9 -5 -2 924.770 23.3837 0 5 -7 -2 1849.00 32.6894 0 7 -5 -1 855.811 28.4189 0 8 -4 -1 1368.06 28.8447 0 4 -6 -1 526.615 20.5475 0 4 -8 -3 1015.51 28.5929 0 8 -6 -2 406.762 20.3652 0 10 -4 -2 753.026 22.4909 0 2 -8 -3 225.421 18.6675 0 6 -6 -1 674.890 28.1189 0 6 -8 -3 161.289 20.5583 0 10 -6 -3 72.6421 19.6412 0 9 -3 -1 376.432 17.3233 0 7 -7 -2 379.237 22.4880 0 11 -5 -3 348.983 22.7416 0 9 -7 -3 28.9331 20.0595 0 4 -8 -2 948.883 28.2326 0 5 -7 -1 1.18241 20.5116 0 3 -7 -1 68.0258 15.2378 0 9 -5 -1 175.489 20.0775 0 8 -6 -1 22.6517 16.1435 0 7 -5 0 745.336 29.1464 0 2 -8 -2 1636.28 32.4455 0 6 -8 -2 187.701 21.4848 0 4 -6 0 429.794 19.8346 0 8 -4 0 1313.47 30.1744 0 10 -6 -2 121.664 19.9591 0 3 -9 -3 54.3450 18.4787 0 10 -4 -1 426.903 27.4322 0 7 -7 -1 941.476 28.4788 0 9 -7 -2 37.6596 18.8003 0 6 -6 0 38.2770 16.4895 0 11 -5 -2 935.457 25.4720 0 10 -2 -1 909.150 19.5047 0 1 -7 -1 5725.69 46.9272 0 1 -9 -3 99.3046 17.7526 0 4 -8 -1 9.66186 15.2481 0 9 -3 0 433.545 18.0174 0 -3 -3 -1 7059.26 21.8010 0 5 -7 0 349.277 27.7618 0 6 -8 -1 83.4348 19.5787 0 0 -8 -2 561.755 19.7687 0 8 -6 0 1.61108 15.7368 0 3 -7 0 503.306 24.2004 0 9 -5 0 108.751 17.4607 0 3 -9 -2 429.317 24.0124 0 10 -6 -1 416.781 23.8652 0 2 -8 -1 164.201 20.3379 0 9 -7 -1 29.1052 21.1904 0 7 -7 0 1232.82 35.0070 0 7 -5 1 323.974 19.8229 0 11 -5 -1 555.933 27.6196 0 4 -6 1 1359.25 27.8464 0 10 -4 0 29.3216 18.3294 0 6 -6 1 501.636 23.4473 0 8 -4 1 1361.79 30.5213 0 1 -9 -2 834.246 27.3526 0 1 -7 0 175.442 16.5262 0 4 -8 0 99.9771 19.7000 0 6 -8 0 121.547 19.9793 0 3 -9 -1 168.659 20.9076 0 5 -7 1 1040.51 30.7888 0 8 -6 1 98.7368 19.7523 0 10 -2 0 85.2955 12.7440 0 9 -7 0 170.225 23.2237 0 0 -8 -1 364.724 19.5649 0 2 -8 0 337.862 24.7193 0 3 -7 1 1898.26 33.9487 0 9 -5 1 296.050 20.0590 0 7 -7 1 117.294 20.4087 0 9 -3 1 630.727 21.4775 0 11 -5 0 475.163 28.6659 0 7 -5 2 551.216 21.1544 0 1 -9 -1 141.793 20.0056 0 4 -6 2 444.421 19.3435 0 6 -6 2 396.789 22.5939 0 10 -4 1 242.383 18.7674 0 4 -8 1 377.871 23.0707 0 6 -8 1 205.368 21.0595 0 3 -9 0 51.2755 21.4635 0 8 -4 2 101.438 14.2131 0 1 -7 1 1848.66 29.0278 0 9 -7 1 150.351 23.1522 0 10 -6 1-0.93844 18.7662 0 5 -7 2 752.332 25.7970 0 8 -6 2 895.275 28.8568 0 -2 -2 0-1151.76 2.02331 0 0 -8 0 172.781 16.0572 0 2 -8 1 149.685 17.8023 0 7 -7 2 315.284 22.3252 0 3 -7 2 841.832 23.7246 0 9 -5 2 490.383 22.2653 0 11 -5 1 508.823 26.3075 0 1 -9 0 19.0744 17.9368 0 6 -8 2 280.356 23.6572 0 3 -9 1 423.438 24.5356 0 9 -3 2 1578.38 26.6386 0 4 -8 2 84.8120 19.6693 0 4 2 -1 1315.30 6.10993 0 6 -6 3 921.687 25.2604 0 9 -7 2 470.942 26.2383 0 10 -4 2 508.190 22.2314 0 10 -6 2 17.3844 19.5110 0 5 -7 3 111.810 17.8172 0 8 -6 3 483.067 23.1780 0 7 -7 3 189.088 20.3927 0 2 -8 2 183.912 18.7182 0 0 -8 1 479.858 19.7635 0 3 -7 3 119.173 15.0894 0 9 -5 3 488.079 21.5332 0 11 -5 2 572.018 26.4200 0 1 -9 1 247.767 19.6541 0 6 -8 3 662.686 27.0232 0 3 -9 2 133.130 19.4573 0 4 -8 3 836.469 26.3666 0 10 -6 3 182.957 21.9570 0 10 -4 3 697.016 22.7648 0 -4 -4 -1 1243.44 11.0240 0 8 -6 4 1.61662 16.0753 0 7 -7 4 252.823 20.6542 0 2 -8 3 883.607 25.7149 0 0 -8 2 688.558 21.1191 0 1 -9 2 95.9090 16.9432 0 11 -5 3 694.559 26.4462 0 3 -9 3 42.2229 18.4738 0 6 -8 4 57.8617 19.8640 0 9 -5 4 246.236 18.9482 0 4 -8 4 146.286 18.0518 0 -3 -3 0 1170.70 9.67433 0 10 -6 4 483.192 25.5564 0 1 -9 3 43.4787 17.0130 0 3 -9 4 34.7552 19.7537 0 6 -8 5-9.26041 20.5422 0 9 -3 4 29.3168 13.7317 0 11 -5 4 285.813 23.1199 0 4 -8 5 45.7831 18.9593 0 -1 -9 2 750.800 23.4980 0 10 -6 5 70.9021 21.8136 0 2 -4 5 40.8846 9.77791 0 1 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106.440 15.7477 0 8 -4 10 95.2759 17.5300 0 4 -6 11-4.58250 16.1591 0 9 -3 9 51.7467 14.9069 0 -2 -6 7 2.62449 9.56699 0 4 0 4 13.2982 5.18442 0 3 -3 9 55.1099 10.9114 0 -4 -4 2-0.31767 3.21540 0 -1 -5 8 52.0723 10.8465 0 0 -8 10 61.0481 16.6820 0 7 -3 10 45.9393 12.2910 0 8 -4 11-8.36605 14.7296 0 4 -6 12 3.20636 15.2028 0 3 -7 12 13.3991 16.4690 0 6 0 5 3.24924 5.51728 0 9 -3 10 61.4138 14.0456 0 5 -5 12 16.7333 15.0742 0 0 -8 11 15.8810 16.5611 0 -2 -8 9 50.4514 14.3615 0 1 -7 12 47.4329 17.2562 0 8 -4 12 79.6548 17.3733 0 7 -1 8 0.92729 8.87275 0 -4 -4 3 4773.10 24.8720 0 3 -5 13-2.80952 14.5808 0 1 -7 13 2.02409 16.6949 0 7 -3 12 32.6377 14.1144 0 8 -4 13 109.774 17.9646 0 0 -6 12 77.9465 15.0626 0 -3 -7 9 0.22606 11.4486 0 5 -1 9 9.68329 8.78757 0 0 -4 11 59.0850 12.4815 0 -3 -7 10 20.7470 12.9726 0 0 -6 13 85.6200 15.9707 0 7 -3 13 60.2335 15.5188 0 -2 -8 12 34.7052 17.2031 0 4 -4 14 22.2775 15.2303 0 -4 -6 8 49.0524 10.6122 0 -1 -7 13 18.1421 16.8100 0 6 -2 12 51.2412 12.7392 0 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-9 -3 -1 732.930 15.4918 8 -9 -3 -11 345.418 20.1407 8 -1 -1 -11 2872.61 27.9201 8 -6 -2 -15 764.812 24.8603 8 -4 -2 -13 735.333 20.7709 8 -7 -3 -11 142.434 15.7895 8 -2 0 -17 1323.56 27.2409 8 -9 -3 -12 180.566 18.5410 8 -5 -3 -7 1500.08 22.8125 8 -5 -3 -6 516.347 14.5413 8 -3 -1 -16 252.180 16.8066 8 -1 -1 -12 1254.47 20.6091 8 -5 -3 -8 337.479 14.8654 8 -2 -2 -7 2125.55 21.8026 8 -5 -3 -5 3104.88 28.1254 8 1 1 -14 1226.75 18.6894 8 -2 -2 -6 4716.11 30.2925 8 -6 -2 -16 352.793 20.8706 8 -4 -2 -14 608.880 20.5951 8 -2 -2 -8 6629.50 39.1262 8 -5 -3 -9 955.578 21.1189 8 -2 -2 -5 1157.93 15.4155 8 -2 -2 -9 2285.37 25.1947 8 0 0 -14 245.128 12.5182 8 -5 -3 -10 159.097 13.3293 8 -1 -1 -13 816.146 18.0561 8 -2 -2 -10 722.117 16.6192 8 -3 -1 -17 322.625 18.1832 8 -5 -3 -11 111.718 12.6732 8 -4 -2 -15 1293.36 27.4752 8 -2 -2 -4 1454.48 15.5918 8 -2 0 4 763.449 6.63232 8 -2 -2 -11 115.309 10.9188 8 -5 -3 -12 424.076 17.5708 8 0 0 -15 328.536 13.8489 8 -1 -1 -14 248.665 13.3781 8 -4 -2 -16 775.733 23.8184 8 -2 -2 -12 4714.21 38.5391 8 -5 -3 -13 149.072 14.9365 8 -10 -4 -7 606.688 20.4609 8 -3 -1 -18 318.403 18.8794 8 -2 -2 -3 5195.69 25.7201 8 -10 -4 -8 105.111 15.6434 8 -10 -4 -6 598.121 19.3956 8 -8 -4 -8 103.298 13.1093 8 -8 -4 -7 454.499 16.7767 8 -10 -4 -5 107.015 12.2063 8 -8 -4 -9 248.938 15.8036 8 -2 -2 -13 1246.58 21.7995 8 -8 -4 -6 432.936 16.0910 8 -1 -1 -15 761.413 18.6845 8 -5 -3 -14 203.825 16.7707 8 -4 -2 -17 175.387 18.0012 8 -10 -4 -4 204.490 13.0144 8 -3 -1 -19 311.699 20.4162 8 -3 -3 -8 371.218 13.5062 8 -2 -2 -14 599.498 18.2465 8 -3 -3 -9 70.6614 10.4857 8 -3 -3 -7 2506.99 25.5728 8 -5 -3 -15 880.179 25.5819 8 -3 -3 -10 4142.85 37.2079 8 -1 -1 -16 570.163 17.8822 8 -3 -3 -6 1904.96 21.8981 8 -6 -4 -8 1102.58 22.4842 8 -3 -3 -11 300.240 14.8117 8 -6 -4 -9 1240.25 24.7277 8 -6 -4 -7 1868.46 27.0974 8 -2 -2 -2 5471.79 24.8904 8 -6 -4 -10 375.751 17.3784 8 -2 -2 -15 408.704 17.5336 8 -6 -4 -6 1661.08 24.5164 8 -5 -3 -16 286.516 20.8178 8 -3 -3 -12 1221.07 23.5830 8 -3 -3 -5 1077.45 16.7691 8 -6 -4 -11 189.471 15.8073 8 -6 -4 -12 803.044 24.0956 8 -1 -1 -17 141.737 14.7403 8 -3 -3 -13 172.226 14.6681 8 -6 -2 3 1213.48 9.77677 8 -2 -2 -16 689.265 21.8655 8 -6 -4 -13 146.764 17.1011 8 -3 -3 -4 483.245 11.4456 8 -3 -3 -14 369.605 17.8876 8 -6 -4 -14 210.523 18.3503 8 1 -1 -9 3103.03 23.9234 8 1 -1 -10 7784.64 39.2598 8 1 -1 -8 2414.61 20.0649 8 1 -1 -11 458.077 12.4326 8 -4 -4 -9 1119.13 23.3577 8 -4 -4 -10 483.643 18.5097 8 -3 -3 -3 738.313 13.2055 8 -4 -4 -8 552.157 17.5054 8 2 0 -10 6085.16 30.6717 8 -4 -4 -11 1134.56 25.6096 8 2 0 -9 3742.49 22.6843 8 -9 -5 -9 1209.28 29.3383 8 -3 -3 -16 529.724 22.6474 8 1 -1 -12 449.294 13.2346 8 -9 -5 -10 263.294 20.2419 8 -9 -5 -8 180.666 17.9863 8 -2 -2 -18 146.146 18.4418 8 2 0 -11 896.363 13.6882 8 -4 -4 -7 1293.58 22.9380 8 1 -1 -7 2779.85 20.4120 8 0 -2 -10 1277.72 19.6008 8 -4 -4 -12 414.275 19.6302 8 0 -2 -9 3838.07 30.0967 8 0 -2 -11 74.0029 10.3850 8 2 0 -8 10022.6 34.2078 8 0 -2 -8 221.204 10.1103 8 -4 -4 -13 0.15306 17.3122 8 2 0 -12 2413.00 22.8113 8 0 -2 -12 1065.57 19.8720 8 -4 -4 -6 211.520 12.1970 8 -3 -3 -17 314.975 21.7150 8 -7 -5 -10 135.758 16.9052 8 0 -2 -7 12690.8 48.3959 8 -7 -5 -9 189.212 17.1732 8 -7 -5 -11 217.478 18.5033 8 0 -2 -13 1325.77 22.7321 8 -7 -5 -8 120.113 15.1929 8 2 0 -13 164.863 9.66882 8 1 -1 -14 1328.19 21.5726 8 1 -1 -6 9809.83 34.9253 8 -7 -5 -12 169.250 19.2015 8 -4 -4 -5 652.768 15.5823 8 2 0 -7 314.214 7.24066 8 -4 -4 -15 306.726 20.0488 8 0 -2 -14 1384.14 24.3299 8 -1 -3 -10 4075.70 35.4095 8 -1 -3 -11 444.030 15.4032 8 -1 -3 -9 4244.95 34.5178 8 0 -2 -6 871.606 13.7683 8 1 -1 -15 147.379 12.8295 8 -1 -3 -12 490.248 16.7441 8 -1 -3 -8 2120.15 23.7966 8 -4 -4 -16 719.048 25.4207 8 -1 -3 -13 473.921 17.1944 8 -4 -4 -4 505.128 13.2642 8 -1 -3 -7 583.014 13.5116 8 -5 -5 -10 1988.94 31.7003 8 -5 -5 -11 135.064 15.4733 8 0 -2 -16 329.386 15.3859 8 -5 -5 -9 196.669 14.6948 8 1 -1 -5 19514.7 44.0668 8 0 -2 -5 23113.5 57.5368 8 -5 -5 -8 466.250 17.6452 8 2 0 -6 636.579 7.93850 8 3 1 -11 494.813 8.98850 8 -1 -3 -6 6077.58 35.8496 8 3 1 -10 279.474 6.90422 8 -5 -5 -14 887.285 27.3016 8 -2 -4 -11 1517.58 26.5583 8 -2 -4 -10 107.985 12.0688 8 -5 -5 -7 1534.67 26.4897 8 0 -2 -17 455.011 18.0627 8 3 1 -9 1876.15 12.8158 8 ; _shelx_hkl_checksum 15668 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2836(3) 0.1185(5) 0.31919(19) 0.0219(6) Uani 1 1 d . . . . . C2 C 0.1500(3) 0.1427(5) 0.3423(2) 0.0266(7) Uani 1 1 d . . . . . H2A H 0.084(4) 0.054(8) 0.317(3) 0.041(12) Uiso 1 1 d . . . . . C3 C 0.1132(3) 0.2878(6) 0.3981(2) 0.0324(7) Uani 1 1 d . . . . . H3A H 0.022(4) 0.300(8) 0.414(3) 0.036(11) Uiso 1 1 d . . . . . C4 C 0.2074(4) 0.4128(6) 0.4337(3) 0.0378(9) Uani 1 1 d . . . . . H4A H 0.188(5) 0.494(11) 0.474(4) 0.058(16) Uiso 1 1 d . . . . . C5 C 0.3401(4) 0.3917(6) 0.4118(3) 0.0387(9) Uani 1 1 d . . . . . H5A H 0.405(5) 0.479(10) 0.436(3) 0.053(14) Uiso 1 1 d . . . . . C6 C 0.3769(3) 0.2450(6) 0.3549(2) 0.0307(7) Uani 1 1 d . . . . . H6A H 0.472(4) 0.215(8) 0.341(3) 0.038(11) Uiso 1 1 d . . . . . C7 C 0.3248(3) -0.0388(5) 0.2576(2) 0.0220(6) Uani 1 1 d . . . . . H7A H 0.424(4) -0.052(7) 0.258(3) 0.026(9) Uiso 1 1 d . . . . . H7B H 0.291(4) -0.156(7) 0.282(3) 0.019(8) Uiso 1 1 d . . . . . C8 C 0.2747(2) -0.0232(4) 0.15389(19) 0.0163(5) Uani 1 1 d . . . . . H8A H 0.316(4) -0.121(7) 0.117(3) 0.024(9) Uiso 1 1 d . . . . . C9 C 0.1216(2) -0.0448(4) 0.13969(18) 0.0164(5) Uani 1 1 d . . . . . O1 O 0.05557(18) 0.0931(3) 0.11370(15) 0.0212(5) Uani 1 1 d . . . . . O2 O 0.07656(17) -0.2033(3) 0.15605(16) 0.0219(5) Uani 1 1 d . . . . . N1 N 0.3153(2) 0.1558(4) 0.11296(18) 0.0178(5) Uani 1 1 d . . . . . H1NA H 0.302(3) 0.144(6) 0.047(2) 0.012(8) Uiso 1 1 d . . . . . H1NB H 0.269(4) 0.235(8) 0.133(3) 0.023(9) Uiso 1 1 d . . . . . H1NC H 0.410(4) 0.192(8) 0.127(3) 0.044(13) Uiso 1 1 d . . . . . O3 O 0.30043(18) 0.5448(3) 0.06643(14) 0.0209(5) Uani 1 1 d . . . . . H3OA H 0.375(5) 0.562(8) 0.089(3) 0.036(11) Uiso 1 1 d . . . . . O4 O 0.2404(2) 0.5124(3) 0.15726(15) 0.0242(5) Uani 1 1 d . . . . . H4OA H 0.180(4) 0.616(9) 0.151(3) 0.042(12) Uiso 1 1 d . . . . . O5 O 0.000000 0.4284(5) 0.000000 0.0237(7) Uani 1 2 d S T P . . H5OA H 0.044(5) 0.357(10) 0.043(4) 0.047(13) 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 0.0204(12) 0.0241(16) 0.0210(11) 0.0013(12) -0.0003(9) -0.0019(11) C2 0.0208(12) 0.0340(19) 0.0248(12) 0.0007(13) 0.0005(10) -0.0022(12) C3 0.0289(14) 0.044(2) 0.0246(13) -0.0035(15) 0.0031(11) 0.0043(15) C4 0.0482(19) 0.036(2) 0.0296(15) -0.0081(16) 0.0076(14) -0.0004(16) C5 0.0418(17) 0.038(2) 0.0366(16) -0.0132(17) 0.0056(14) -0.0154(17) C6 0.0257(13) 0.036(2) 0.0303(14) -0.0041(15) 0.0033(11) -0.0100(13) C7 0.0161(11) 0.0184(15) 0.0314(13) 0.0034(12) -0.0023(9) -0.0016(10) C8 0.0110(10) 0.0106(13) 0.0274(12) -0.0009(11) 0.0014(9) -0.0013(9) C9 0.0104(10) 0.0151(13) 0.0240(11) -0.0029(11) 0.0030(8) -0.0021(9) O1 0.0153(8) 0.0145(10) 0.0336(10) 0.0023(9) -0.0004(7) -0.0001(7) O2 0.0120(8) 0.0128(10) 0.0409(11) 0.0009(9) 0.0026(7) -0.0024(8) N1 0.0122(9) 0.0116(12) 0.0298(12) 0.0002(9) 0.0027(8) -0.0028(8) O3 0.0148(9) 0.0214(12) 0.0268(9) 0.0021(9) 0.0020(7) -0.0008(7) O4 0.0260(9) 0.0156(10) 0.0317(10) 0.0045(9) 0.0093(8) 0.0044(8) O5 0.0193(12) 0.0191(16) 0.0330(15) 0.000 0.0035(11) 0.000 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' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1CE00688F 2021 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 117.7(3) . . ? C6 C1 C7 120.8(3) . . ? C2 C1 C7 121.5(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2A 121(3) . . ? C1 C2 H2A 118(3) . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3A 120(3) . . ? C4 C3 H3A 119(3) . . ? C3 C4 C5 119.3(4) . . ? C3 C4 H4A 122(4) . . ? C5 C4 H4A 118(4) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5A 119(3) . . ? C6 C5 H5A 121(3) . . ? C1 C6 C5 121.4(3) . . ? C1 C6 H6A 114(3) . . ? C5 C6 H6A 124(3) . . ? C1 C7 C8 114.6(3) . . ? C1 C7 H7A 111(3) . . ? C8 C7 H7A 107(2) . . ? C1 C7 H7B 110(2) . . ? C8 C7 H7B 107(2) . . ? H7A C7 H7B 106(3) . . ? N1 C8 C7 110.9(2) . . ? N1 C8 C9 109.0(2) . . ? C7 C8 C9 113.1(2) . . ? N1 C8 H8A 107(3) . . ? C7 C8 H8A 109(2) . . ? C9 C8 H8A 107(2) . . ? O1 C9 O2 126.6(2) . . ? O1 C9 C8 117.9(2) . . ? O2 C9 C8 115.5(2) . . ? C8 N1 H1NA 106(3) . . ? C8 N1 H1NB 108(3) . . ? H1NA N1 H1NB 110(4) . . ? C8 N1 H1NC 115(3) . . ? H1NA N1 H1NC 108(3) . . ? H1NB N1 H1NC 108(4) . . ? O4 O3 H3OA 95(3) . . ? O3 O4 H4OA 95(3) . . ? H5OA O5 H5OA 110(8) . 2 ? 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 1.380(5) . ? C1 C2 1.397(4) . ? C1 C7 1.498(5) . ? C2 C3 1.370(5) . ? C2 H2A 0.97(5) . ? C3 C4 1.378(6) . ? C3 H3A 0.95(4) . ? C4 C5 1.381(5) . ? C4 H4A 0.84(7) . ? C5 C6 1.388(6) . ? C5 H5A 0.96(6) . ? C6 H6A 1.01(4) . ? C7 C8 1.530(4) . ? C7 H7A 1.00(4) . ? C7 H7B 0.98(5) . ? C8 N1 1.477(4) . ? C8 C9 1.537(3) . ? C8 H8A 0.98(5) . ? C9 O1 1.237(4) . ? C9 O2 1.253(4) . ? N1 H1NA 0.94(3) . ? N1 H1NB 0.80(5) . ? N1 H1NC 0.99(4) . ? O3 O4 1.462(3) . ? O3 H3OA 0.80(5) . ? O4 H4OA 0.96(6) . ? O5 H5OA 0.90(6) . ? O5 H5OA 0.90(6) 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 _geom_hbond_publ_flag C8 H8A O3 0.98(5) 2.51(5) 3.362(4) 145(3) 1_545 yes C8 H8A O5 0.98(5) 2.56(4) 3.221(3) 125(3) 3_545 yes N1 H1NA O3 0.94(3) 1.99(3) 2.849(3) 151(3) 4_545 yes N1 H1NB O3 0.80(5) 2.44(5) 2.879(3) 116(4) . yes N1 H1NB O4 0.80(5) 2.05(6) 2.755(4) 148(4) . yes N1 H1NC O2 0.99(4) 1.85(5) 2.833(3) 171(5) 3 yes O3 H3OA O1 0.80(5) 1.83(5) 2.621(3) 168(4) 3 yes O4 H4OA O2 0.96(6) 1.66(6) 2.618(3) 173(4) 1_565 yes O5 H5OA O1 0.90(6) 2.15(7) 2.938(3) 147(5) . yes 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 C3 0.4(5) . . . . ? C7 C1 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C2 C1 C6 C5 -0.1(5) . . . . ? C7 C1 C6 C5 179.8(3) . . . . ? C4 C5 C6 C1 0.0(6) . . . . ? C6 C1 C7 C8 -110.4(3) . . . . ? C2 C1 C7 C8 69.5(4) . . . . ? C1 C7 C8 N1 54.6(3) . . . . ? C1 C7 C8 C9 -68.2(3) . . . . ? N1 C8 C9 O1 -12.0(3) . . . . ? C7 C8 C9 O1 111.9(3) . . . . ? N1 C8 C9 O2 168.0(2) . . . . ? C7 C8 C9 O2 -68.1(3) . . . . ?