#------------------------------------------------------------------------------ #$Date: 2019-02-03 22:01:58 +0200 (Sun, 03 Feb 2019) $ #$Revision: 213452 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/14/2021472.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_2021472 loop_ _publ_author_name 'Sabbaghi, Fahimeh' 'Pourayoubi, Mehrdad' 'Ne\S)-(--)-\a-methylbenzylamido]phosphate ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _cell_angle_alpha 90 _cell_angle_beta 113.686(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.3482(3) _cell_length_b 7.35890(10) _cell_length_c 11.8714(3) _cell_measurement_reflns_used 4360 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.4570 _cell_measurement_theta_min 2.7760 _cell_volume 907.87(4) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_data_collection ; Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014) MSCServDetCCD = {5.7.3.4} ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; enCIFer (Allen et al., 2004) ; _computing_structure_refinement ; SHELXL2018 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT2014 (Sheldrick, 2015a) ; _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'AFC11 (Right): Eulerian 3 circle CCD' _diffrn_measurement_method 'Profile data from \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.334 _diffrn_reflns_theta_min 3.210 _diffrn_source 'Rotating Anode MicroMax-007HF DW 1.2 kW' _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2015) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.293 _exptl_crystal_description plate _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.150 _refine_diff_density_min -0.206 _refine_ls_abs_structure_details ; Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack 0.06(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 2908 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0252 _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^)+(0.0462P)^2^+0.0982P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.0686 _reflns_number_gt 2858 _reflns_number_total 2908 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ky3152sup1.cif _cod_data_source_block II _cod_database_code 2021472 _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 0.959 _shelx_estimated_absorpt_t_max 0.992 _shelx_hkl_file ; 0 -10 1 128.69 10.00 0 -10 2 104.79 9.60 0 -10 3 123.79 11.00 0 -9 0 -1.20 2.60 0 -9 0 -0.90 2.30 0 -9 -1 9.30 3.20 0 -9 1 10.50 2.80 0 -9 -1 8.10 2.80 0 -9 1 7.80 3.30 0 -9 2 139.59 9.90 0 -9 -2 158.68 8.40 0 -9 2 163.28 10.70 0 -9 3 55.99 7.00 0 -9 4 13.50 4.20 0 -9 5 49.90 7.40 0 -8 0 89.79 6.90 0 -8 0 94.79 6.90 0 -8 -1 196.98 9.20 0 -8 -1 186.58 9.00 0 -8 1 202.28 10.30 0 -8 1 208.08 10.70 0 -8 -2 222.58 9.10 0 -8 2 216.28 11.20 0 -8 2 221.08 11.40 0 -8 -2 217.18 9.00 0 -8 -3 209.38 8.00 0 -8 3 207.38 11.70 0 -8 3 216.58 11.80 0 -8 -3 202.18 7.90 0 -8 -4 70.79 4.00 0 -8 4 67.99 7.40 0 -8 4 64.69 7.00 0 -8 -4 70.39 4.10 0 -8 5 146.29 10.70 0 -8 6 11.20 4.10 0 -8 7 32.90 7.00 0 -7 0 5.90 2.30 0 -7 -1 46.70 4.30 0 -7 1 43.30 4.60 0 -7 1 52.09 4.90 0 -7 -2 263.57 9.10 0 -7 2 264.47 11.70 0 -7 -2 259.97 8.90 0 -7 2 283.97 11.80 0 -7 -3 643.44 12.80 0 -7 3 628.34 19.00 0 -7 -3 661.93 13.00 0 -7 3 622.34 18.50 0 -7 -4 110.09 4.70 0 -7 4 111.79 8.50 0 -7 4 129.29 8.90 0 -7 -4 120.39 4.80 0 -7 5 430.96 17.00 0 -7 5 404.76 16.20 0 -7 6 299.37 14.60 0 -7 6 283.07 14.30 0 -7 7 559.24 21.00 0 -7 8 130.19 10.90 0 -6 0 1493.15 22.80 0 -6 -1 246.48 8.70 0 -6 1 213.28 9.20 0 -6 -2 390.36 10.00 0 -6 2 394.96 13.20 0 -6 3 1525.85 27.10 0 -6 -3 1512.55 17.70 0 -6 4 274.67 12.10 0 -6 -4 285.07 6.60 0 -6 -4 281.97 6.50 0 -6 4 281.37 12.10 0 -6 5 248.78 12.10 0 -6 5 261.57 12.20 0 -6 6 52.59 6.10 0 -6 6 49.50 5.80 0 -6 7 255.57 13.40 0 -6 7 259.37 13.30 0 -6 8 166.28 11.20 0 -6 8 182.68 11.70 0 -6 9 198.28 13.10 0 -6 10 181.68 13.10 0 -5 0 0.50 0.90 0 -5 1 67.09 4.90 0 -5 -1 62.59 4.00 0 -5 2 107.19 6.40 0 -5 -2 114.49 4.90 0 -5 3 2299.27 30.70 0 -5 -3 2390.56 19.40 0 -5 -4 766.22 9.30 0 -5 4 755.02 18.50 0 -5 5 2425.76 34.20 0 -5 5 2432.86 34.80 0 -5 6 1177.38 25.40 0 -5 6 1162.98 24.80 0 -5 7 2287.47 36.30 0 -5 7 2242.88 36.70 0 -5 8 601.24 19.90 0 -5 8 692.23 21.10 0 -5 9 93.79 8.30 0 -5 9 99.29 8.80 0 -5 10 360.96 17.00 0 -5 11 107.79 10.10 0 -4 0 2495.35 23.70 0 -4 1 1085.79 17.10 0 -4 -1 1137.99 14.40 0 -4 2 543.45 12.80 0 -4 -2 572.34 9.20 0 -4 3 2518.85 29.40 0 -4 -3 2601.74 17.00 0 -4 -4 670.93 7.20 0 -4 4 681.93 16.30 0 -4 5 119.09 7.30 0 -4 6 170.08 8.90 0 -4 6 167.98 9.10 0 -4 7 1261.17 25.30 0 -4 7 1246.68 25.70 0 -4 8 87.19 7.30 0 -4 8 67.39 6.20 0 -4 9 130.19 9.00 0 -4 9 135.49 9.50 0 -4 10 74.19 7.40 0 -4 10 83.99 8.00 0 -4 11 103.49 9.40 0 -4 12 184.98 12.80 0 -3 0 0.80 0.70 0 -3 -1 312.97 6.40 0 -3 1 309.27 7.90 0 -3 2 1474.55 18.80 0 -3 -2 1477.85 11.90 0 -3 -3 96.69 2.60 0 -3 -4 657.43 5.90 0 -3 -5 977.80 7.20 0 -3 6 1390.16 23.40 0 -3 7 282.17 11.20 0 -3 8 166.68 9.10 0 -3 9 423.46 15.20 0 -3 9 431.76 15.70 0 -3 10 67.49 6.70 0 -3 10 65.69 6.60 0 -3 11 48.70 6.10 0 -3 11 52.29 6.30 0 -3 12 2.30 3.00 0 -3 12 -1.80 2.90 0 -3 13 25.00 5.40 0 -2 -1 1881.51 11.90 0 -2 -2 29.70 1.20 0 -2 -3 592.44 5.20 0 -2 -4 1298.77 9.10 0 -2 5 1134.59 18.10 0 -2 6 791.42 16.20 0 -2 7 442.76 13.00 0 -2 8 367.66 12.70 0 -2 9 368.46 13.30 0 -2 10 325.27 13.30 0 -2 10 316.57 13.00 0 -2 11 135.49 9.10 0 -2 11 137.69 9.30 0 -2 12 105.19 8.60 0 -2 12 97.59 8.10 0 -2 13 118.09 9.50 0 -2 13 110.29 9.20 0 -2 14 65.39 8.00 0 -1 0 12.00 0.80 0 -1 -3 662.53 6.70 0 -1 4 3520.05 26.20 0 -1 5 951.20 15.00 0 -1 6 1410.66 19.90 0 -1 7 477.35 12.30 0 -1 8 1391.46 22.40 0 -1 9 812.22 18.30 0 -1 10 637.94 17.30 0 -1 11 347.67 13.70 0 -1 11 332.47 13.10 0 -1 12 10.40 3.00 0 -1 12 12.30 3.30 0 -1 13 38.40 5.50 0 -1 13 49.80 6.20 0 -1 14 17.20 4.60 0 -1 14 14.80 4.40 0 -1 15 10.70 4.60 0 0 3 344.17 6.10 0 0 4 2243.48 18.20 0 0 5 2244.78 20.50 0 0 6 175.28 6.30 0 0 7 198.48 7.30 0 0 8 1.90 1.30 0 0 9 1298.77 21.50 0 0 10 1218.78 22.00 0 0 11 756.92 18.50 0 0 11 721.13 18.40 0 0 12 138.99 8.50 0 0 12 132.79 8.40 0 0 13 164.18 9.70 0 0 13 170.88 10.00 0 0 14 15.00 4.30 0 0 14 12.10 4.10 0 1 3 808.12 7.20 0 1 4 3508.25 18.80 0 1 5 968.30 11.50 0 1 6 1314.87 15.10 0 1 7 449.66 9.80 0 1 8 1388.26 18.80 0 1 9 831.22 15.60 0 1 10 630.44 14.50 0 1 11 337.47 11.40 0 1 11 328.87 11.40 0 1 12 17.40 3.10 0 1 12 14.30 2.90 0 1 13 45.00 5.10 0 1 13 40.20 4.70 0 1 14 15.50 3.70 0 2 1 1892.71 12.00 0 2 2 30.50 1.30 0 2 3 609.64 5.30 0 2 4 1337.77 9.30 0 2 5 1145.59 10.30 0 2 6 789.12 9.90 0 2 7 457.15 8.50 0 2 8 361.16 8.30 0 2 9 344.77 8.90 0 2 10 292.77 8.90 0 2 10 307.57 9.30 0 2 11 143.19 6.80 0 2 11 131.69 6.40 0 2 12 99.09 5.90 0 2 12 109.29 6.40 0 2 13 100.59 6.50 0 2 13 101.69 6.40 0 3 3 122.49 3.00 0 3 4 662.43 6.00 0 3 5 962.00 7.30 0 3 6 1269.57 9.60 0 3 7 311.47 5.50 0 3 8 157.98 4.40 0 3 9 423.96 8.00 0 3 9 411.46 8.10 0 3 10 53.99 3.30 0 3 10 63.99 3.40 0 3 11 54.79 3.40 0 3 11 58.89 3.60 0 3 12 3.40 1.40 0 3 12 2.10 1.40 -1 -10 3 37.90 6.90 -1 -10 2 17.00 5.50 1 -10 1 193.78 12.00 1 -10 2 167.18 11.90 -1 -9 5 168.28 11.90 -1 -9 4 93.09 9.00 -1 -9 3 261.17 14.10 -1 -9 3 300.37 15.00 -1 -9 2 418.76 16.80 1 -9 -2 451.65 13.90 -1 -9 2 424.26 17.00 -1 -9 1 882.41 23.00 -1 -9 1 886.81 23.30 1 -9 -1 849.32 20.60 1 -9 -1 870.01 20.80 -1 -9 0 429.56 15.50 -1 -9 0 429.06 15.60 1 -9 0 423.86 15.50 1 -9 0 440.66 15.90 -1 -9 -1 8.40 2.40 1 -9 1 18.80 4.30 -1 -9 -1 26.20 4.40 1 -9 1 19.60 4.30 1 -9 2 6.30 3.20 1 -9 2 6.00 3.10 -1 -9 -2 5.00 2.40 1 -9 3 61.49 7.00 1 -9 4 29.20 5.60 -1 -8 7 91.49 9.40 -1 -8 6 20.30 4.50 -1 -8 5 12.60 4.00 -1 -8 5 6.80 3.50 1 -8 -4 43.50 3.30 1 -8 -4 46.00 3.20 -1 -8 4 43.50 5.80 -1 -8 4 34.60 5.30 1 -8 -3 32.00 3.40 1 -8 -3 26.60 3.20 -1 -8 3 26.80 4.80 1 -8 -2 430.36 12.60 -1 -8 2 455.05 16.30 1 -8 -2 436.36 12.80 1 -8 -1 186.58 9.10 -1 -8 1 184.48 10.00 1 -8 -1 180.18 8.90 -1 -8 0 215.98 10.30 1 -8 0 204.18 10.20 1 -8 0 203.18 9.90 1 -8 1 513.75 16.90 1 -8 1 528.85 16.80 -1 -8 -1 508.35 14.80 1 -8 2 754.02 21.30 -1 -8 -2 778.22 17.20 1 -8 2 754.32 21.20 -1 -8 -3 370.86 10.90 1 -8 3 378.76 16.10 -1 -8 -3 363.66 10.70 1 -8 3 368.76 15.50 1 -8 4 143.29 10.20 -1 -8 -4 146.79 6.00 1 -8 4 133.29 10.10 -1 -8 -4 130.39 5.70 1 -8 5 38.30 6.00 1 -8 6 61.29 7.80 -1 -7 9 129.09 11.30 -1 -7 8 95.29 9.20 -1 -7 7 255.87 14.10 -1 -7 7 286.07 15.00 -1 -7 6 253.67 13.40 -1 -7 6 228.98 12.70 -1 -7 5 40.30 5.30 1 -7 -4 313.47 7.60 -1 -7 4 306.07 13.60 1 -7 -4 310.07 7.40 1 -7 -3 252.77 8.00 1 -7 -3 251.27 8.00 -1 -7 3 251.17 11.80 1 -7 -2 317.27 9.90 -1 -7 2 281.57 12.00 1 -7 -2 305.07 9.90 -1 -7 1 630.04 17.10 1 -7 -1 675.63 15.60 1 -7 -1 648.94 15.50 1 -7 0 447.96 13.80 -1 -7 0 449.66 13.70 1 -7 0 460.85 13.70 -1 -7 -1 38.20 3.90 1 -7 1 34.90 4.30 1 -7 1 35.70 4.40 1 -7 2 41.60 4.90 -1 -7 -2 43.00 3.90 1 -7 2 49.60 5.10 -1 -7 -3 190.88 7.20 1 -7 3 187.28 10.20 1 -7 3 183.28 10.40 1 -7 4 191.78 11.10 1 -7 4 182.58 10.60 -1 -7 -4 177.78 6.30 -1 -7 -5 207.08 5.50 -1 -7 -5 210.68 5.50 1 -7 5 231.38 12.70 1 -7 5 216.98 12.10 1 -7 6 413.96 17.40 1 -7 6 396.46 17.30 1 -7 7 264.07 14.80 1 -7 8 313.67 16.80 -1 -6 10 203.08 13.40 -1 -6 9 107.99 9.40 -1 -6 8 583.64 20.40 -1 -6 8 589.84 20.70 -1 -6 7 299.27 13.90 -1 -6 7 284.07 13.90 -1 -6 6 33.30 4.90 -1 -6 5 45.20 5.20 1 -6 -4 96.49 3.60 -1 -6 4 94.89 7.10 1 -6 -4 89.99 3.60 1 -6 -3 -0.40 0.70 -1 -6 3 0.20 1.80 1 -6 -3 2.50 0.90 -1 -6 2 154.78 8.20 1 -6 -2 153.68 6.40 1 -6 -2 149.88 6.10 -1 -6 1 222.68 9.30 1 -6 -1 218.78 8.30 1 -6 -1 204.18 7.90 1 -6 0 157.68 7.30 -1 -6 0 153.98 7.40 1 -6 0 136.89 7.00 1 -6 1 24.70 3.20 -1 -6 -1 25.30 3.00 1 -6 1 28.70 3.50 1 -6 2 2136.59 31.00 -1 -6 -2 2221.48 24.40 1 -6 2 2132.49 30.20 1 -6 3 1100.59 23.30 1 -6 3 1112.09 23.10 -1 -6 -3 1118.89 15.90 -1 -6 -4 269.27 7.10 1 -6 4 261.47 11.80 1 -6 4 266.17 12.10 -1 -6 -5 136.59 4.30 1 -6 5 143.69 9.40 1 -6 5 150.88 9.40 1 -6 6 172.48 10.70 1 -6 6 175.78 10.80 1 -6 7 469.35 18.40 1 -6 7 459.25 18.00 1 -6 8 66.49 7.60 1 -6 9 7.90 3.60 -1 -5 11 -0.90 2.90 -1 -5 10 149.39 10.60 -1 -5 10 161.88 11.30 -1 -5 9 276.17 14.10 -1 -5 9 259.77 13.40 -1 -5 8 209.78 11.40 -1 -5 8 133.99 9.40 -1 -5 7 80.09 7.00 -1 -5 6 298.17 12.60 -1 -5 5 170.48 9.10 1 -5 -4 2022.00 13.60 1 -5 -4 2033.50 13.70 -1 -5 3 2187.18 29.90 1 -5 -3 2223.78 18.30 1 -5 -2 75.79 3.90 1 -5 -2 74.69 3.90 -1 -5 2 68.99 5.10 1 -5 -1 95.29 5.00 -1 -5 1 96.49 5.60 1 -5 -1 101.39 5.00 -1 -5 0 177.68 7.20 1 -5 0 171.98 7.00 1 -5 0 164.78 7.00 1 -5 1 20.10 2.70 -1 -5 -1 20.50 2.40 1 -5 1 19.60 2.70 1 -5 2 160.08 7.70 1 -5 2 148.89 7.60 -1 -5 -2 169.38 6.10 1 -5 3 135.29 7.40 -1 -5 -3 136.29 5.00 1 -5 3 131.59 7.50 -1 -5 -4 187.18 5.30 1 -5 4 197.58 9.70 1 -5 4 203.58 9.70 -1 -5 -5 153.08 4.30 1 -5 5 154.18 8.70 1 -5 5 154.48 9.10 1 -5 6 573.84 18.30 1 -5 6 567.14 17.80 1 -5 7 774.82 22.00 1 -5 7 791.72 22.40 1 -5 8 321.47 14.80 1 -5 8 303.27 14.70 1 -5 9 194.48 12.30 1 -5 9 198.28 12.10 1 -5 10 104.39 9.40 1 -5 11 280.97 16.20 -1 -4 13 126.59 11.10 -1 -4 12 207.28 13.10 -1 -4 11 51.69 6.60 -1 -4 11 66.59 7.20 -1 -4 10 122.09 9.10 -1 -4 10 150.48 10.20 -1 -4 9 622.44 19.20 -1 -4 9 604.34 19.20 -1 -4 8 824.72 21.60 -1 -4 8 830.52 21.20 -1 -4 7 509.05 16.20 -1 -4 6 292.57 11.70 -1 -4 5 784.72 18.10 -1 -4 4 1113.39 20.50 1 -4 -3 570.24 7.60 -1 -4 3 553.54 13.60 1 -4 -3 564.14 7.50 -1 -4 2 4689.33 37.60 1 -4 -2 4611.44 26.60 1 -4 -2 4669.73 26.10 1 -4 -1 676.13 11.50 1 -4 -1 680.43 11.20 -1 -4 1 657.03 13.10 1 -4 0 666.13 12.30 1 -4 0 670.73 12.50 -1 -4 0 686.83 12.50 1 -4 1 4199.08 33.30 -1 -4 -1 4263.67 28.70 -1 -4 -2 5995.50 31.60 1 -4 2 5872.81 42.40 -1 -4 -3 3091.59 21.00 1 -4 3 3029.30 32.40 -1 -4 -4 1382.76 13.20 1 -4 4 1378.06 23.20 -1 -4 -5 1459.85 12.70 1 -4 5 1519.25 25.70 -1 -4 -6 2119.49 15.20 1 -4 6 2153.78 32.30 1 -4 7 725.53 19.70 1 -4 8 62.59 6.40 1 -4 9 154.58 10.10 1 -4 10 33.90 5.80 1 -4 10 29.00 5.00 1 -4 11 71.79 8.00 1 -4 12 31.60 6.40 -1 -3 14 67.19 8.20 -1 -3 13 37.60 6.00 -1 -3 12 91.69 8.60 -1 -3 12 94.29 8.60 -1 -3 11 71.79 7.00 -1 -3 11 77.29 7.30 -1 -3 10 224.18 11.70 -1 -3 10 257.87 12.20 -1 -3 9 1183.68 25.20 -1 -3 9 1206.78 25.00 -1 -3 8 31.10 4.00 -1 -3 8 25.20 3.70 -1 -3 7 846.92 19.30 -1 -3 6 754.42 17.30 -1 -3 5 475.25 12.90 -1 -3 4 2737.43 29.10 1 -3 -2 1266.07 11.00 -1 -3 2 1288.57 17.40 1 -3 -2 1271.17 10.90 -1 -3 1 2497.05 22.50 1 -3 -1 2530.05 18.20 -1 -3 0 2110.29 19.10 1 -3 0 2082.39 18.70 -1 -3 -1 514.35 8.60 1 -3 1 507.75 10.30 1 -3 2 443.86 10.50 -1 -3 -2 434.36 7.30 -1 -3 -3 8.30 1.10 1 -3 3 7.20 1.80 -1 -3 -4 161.88 4.30 1 -3 4 162.38 7.30 -1 -3 -5 274.47 5.80 1 -3 5 273.87 10.20 1 -3 6 2583.94 32.80 -1 -3 -6 2632.34 19.00 1 -3 7 418.36 14.00 1 -3 8 2102.89 32.90 1 -3 9 1267.27 27.10 1 -3 10 38.80 5.20 1 -3 11 264.17 14.00 1 -3 11 251.17 13.50 1 -3 12 110.39 9.60 1 -3 13 54.49 7.60 -1 -2 15 20.10 5.40 -1 -2 14 44.30 6.40 -1 -2 13 262.77 13.50 -1 -2 13 285.37 14.30 -1 -2 12 247.98 12.70 -1 -2 12 241.28 12.40 -1 -2 11 103.29 7.70 -1 -2 11 100.39 7.90 -1 -2 10 768.62 19.90 -1 -2 10 739.73 19.20 -1 -2 9 1302.97 24.70 -1 -2 9 1330.67 24.60 -1 -2 8 410.96 13.00 -1 -2 8 423.86 13.40 -1 -2 7 444.26 12.90 -1 -2 6 2004.90 25.70 -1 -2 5 386.96 10.60 -1 -2 4 2271.17 23.80 -1 -2 3 2993.00 25.20 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6 2511.35 23.50 -4 0 5 108.89 4.80 4 0 -5 113.39 4.80 -4 0 4 220.08 6.50 4 0 -4 230.58 6.70 4 0 -3 1982.90 19.10 -4 0 3 1963.40 18.90 -4 0 2 1901.61 18.70 4 0 -2 1912.01 18.80 4 0 -1 1111.29 14.70 -4 0 1 1119.59 14.60 -4 0 0 61.79 3.60 4 0 0 42.00 2.90 -4 0 -1 83.79 4.40 4 0 1 90.49 4.60 -4 0 -2 1122.39 16.90 4 0 2 1133.79 17.10 4 0 3 763.92 14.70 -4 0 -3 722.53 14.40 4 0 4 17.60 2.50 -4 0 -4 21.40 2.70 4 0 5 863.31 17.70 -4 0 -5 847.52 17.40 -4 0 -6 537.35 14.50 4 0 6 503.95 14.30 4 0 7 347.17 12.40 -4 0 -7 360.66 12.60 4 0 8 366.16 13.40 -4 0 -8 347.17 13.10 4 0 9 103.89 7.70 4 0 10 659.93 20.00 4 0 11 312.27 14.50 -4 1 14 177.48 8.60 -4 1 14 180.38 8.70 -4 1 13 103.79 6.30 -4 1 13 100.29 6.30 -4 1 12 211.68 8.40 -4 1 12 216.08 8.60 -4 1 11 92.19 5.40 -4 1 11 95.79 5.50 -4 1 10 20.60 2.60 -4 1 9 1489.55 18.90 -4 1 8 2316.37 22.10 -4 1 7 1994.80 19.40 4 1 -7 1952.40 24.60 4 1 -6 237.28 8.20 -4 1 6 232.28 6.30 -4 1 5 1898.61 17.30 4 1 -5 1832.22 21.50 -4 1 4 1982.00 17.40 4 1 -4 1994.10 21.40 -4 1 3 2955.60 21.70 4 1 -3 3000.60 25.30 4 1 -2 4034.40 29.20 -4 1 2 4047.89 26.40 4 1 -1 2978.80 24.90 -4 1 1 3042.40 24.20 4 1 0 26.70 2.50 -4 1 0 27.80 2.60 4 1 1 1636.54 19.40 -4 1 -1 1384.76 18.50 -4 1 -2 3824.22 32.50 4 1 2 3861.81 30.90 -4 1 -3 987.70 17.50 4 1 3 1004.60 16.60 4 1 4 295.07 9.40 -4 1 -4 293.87 10.20 -4 1 -5 401.26 12.50 4 1 5 417.56 11.90 4 1 6 1267.67 21.80 -4 1 -6 1297.77 23.70 -4 1 -7 875.91 20.60 4 1 7 846.52 18.50 4 1 8 89.79 6.40 4 1 9 20.60 3.60 4 1 10 -0.40 2.50 4 1 11 37.70 5.30 4 1 12 24.50 4.80 -4 2 14 22.30 2.80 -4 2 14 25.60 2.80 -4 2 13 775.32 14.20 -4 2 13 810.22 14.20 -4 2 12 27.90 2.80 -4 2 12 30.50 2.80 -4 2 11 576.24 10.90 -4 2 11 579.34 10.90 -4 2 10 461.95 9.20 -4 2 10 441.76 8.90 -4 2 9 33.10 2.40 -4 2 8 133.49 4.30 -4 2 7 654.33 9.10 4 2 -7 647.34 15.40 4 2 -6 895.01 17.40 -4 2 6 874.41 10.20 4 2 -5 594.54 13.50 -4 2 5 603.34 8.60 -4 2 4 1311.17 13.30 4 2 -4 1332.47 19.30 -4 2 3 1490.35 15.10 4 2 -3 1160.18 17.20 4 2 -2 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5 116.99 9.90 -5 -8 4 42.50 6.10 5 -8 -4 46.80 4.30 5 -8 -4 48.60 4.20 5 -8 -3 44.60 4.60 -5 -8 3 49.99 6.30 5 -8 -3 45.00 4.60 -5 -8 2 66.69 7.00 5 -8 -2 65.29 5.90 5 -8 -2 68.09 6.00 -5 -8 1 177.58 10.60 5 -8 -1 171.98 9.80 5 -8 -1 167.78 9.90 -5 -8 0 206.28 11.10 5 -8 0 183.78 10.80 5 -8 0 195.88 11.00 5 -8 1 257.97 13.50 -5 -8 -1 271.87 12.30 5 -8 1 277.37 13.60 -5 -8 -2 194.88 10.10 -5 -8 -3 119.69 7.80 -5 -7 9 146.39 11.70 -5 -7 8 190.08 12.70 -5 -7 7 46.10 6.20 5 -7 -6 108.69 2.90 -5 -7 6 177.98 11.50 5 -7 -5 432.26 9.50 5 -7 -5 406.86 9.50 -5 -7 5 403.86 16.50 5 -7 -4 501.65 12.40 5 -7 -4 519.45 12.30 -5 -7 4 508.55 18.00 -5 -7 3 380.86 15.20 5 -7 -3 360.06 11.40 -5 -7 2 66.59 6.30 5 -7 -2 59.79 5.30 -5 -7 1 104.59 7.50 5 -7 -1 102.39 7.10 -5 -7 0 58.79 5.80 5 -7 0 57.39 5.80 -5 -7 -1 31.80 4.30 5 -7 1 30.10 4.60 5 -7 2 50.59 6.00 -5 -7 -2 48.20 4.70 5 -7 3 231.18 12.90 -5 -7 -3 229.78 10.20 -5 -7 -4 6.40 2.30 -5 -7 -5 245.68 9.80 -5 -6 11 159.08 12.40 -5 -6 10 81.19 8.60 -5 -6 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6 91.69 6.80 10 0 -5 55.09 5.40 -10 0 5 57.19 5.60 10 0 -4 30.90 4.40 -10 0 4 24.30 4.00 10 0 -3 482.65 16.20 -10 0 3 513.45 16.40 -10 0 2 80.49 6.80 10 0 -2 78.89 6.80 -10 0 1 118.69 8.20 10 0 -1 115.99 8.40 -10 0 0 574.24 18.50 10 0 0 575.74 18.70 10 0 1 589.64 19.40 -10 0 -1 580.84 19.00 -10 0 -2 21.40 4.40 10 0 2 20.70 4.30 10 0 3 182.18 11.60 -10 0 -3 205.08 12.20 -10 0 -4 371.76 16.80 -10 0 -5 154.68 11.30 -10 1 14 133.89 8.60 -10 1 13 250.67 11.50 10 1 -13 259.17 13.50 -10 1 12 69.99 6.10 10 1 -12 66.89 7.10 -10 1 11 526.25 16.20 10 1 -11 514.65 18.10 -10 1 10 600.64 17.00 10 1 -10 586.04 18.80 -10 1 9 208.88 10.00 10 1 -9 218.08 11.30 -10 1 8 1144.19 23.40 10 1 -8 1151.18 25.60 -10 1 7 217.48 10.20 10 1 -7 227.38 11.30 -10 1 6 381.66 13.60 10 1 -6 392.26 14.70 10 1 -5 221.68 11.10 -10 1 5 191.88 9.80 -10 1 4 2911.61 38.40 10 1 -4 2879.71 39.80 10 1 -3 783.62 20.80 -10 1 3 833.72 21.10 10 1 -2 142.09 9.00 -10 1 2 212.78 10.80 10 1 -1 566.04 18.20 -10 1 1 577.44 18.20 10 1 0 1083.99 25.80 -10 1 0 1174.68 26.50 10 1 1 108.59 8.60 -10 1 -1 136.39 9.50 10 1 2 62.69 6.90 -10 1 -2 62.99 6.90 -10 1 -3 259.67 13.90 10 1 3 254.57 13.50 -10 1 -4 16.20 4.10 -10 1 -5 18.90 4.80 -10 2 13 38.90 4.50 -10 2 12 25.10 3.50 10 2 -12 31.20 5.60 -10 2 11 24.00 3.60 10 2 -11 29.60 5.10 10 2 -10 157.78 10.50 -10 2 10 156.58 8.30 10 2 -9 759.42 22.00 -10 2 9 750.22 18.10 10 2 -8 418.96 16.30 -10 2 8 427.76 13.80 -10 2 7 224.18 10.20 10 2 -7 240.28 12.20 -10 2 6 119.09 7.60 10 2 -6 110.29 8.20 -10 2 5 169.78 9.20 10 2 -5 162.58 9.70 -10 2 4 284.57 12.00 10 2 -4 263.17 12.40 10 2 -3 525.45 17.80 -10 2 3 497.65 16.20 10 2 -2 734.93 20.90 -10 2 2 705.43 19.60 10 2 -1 598.14 19.00 -10 2 1 585.84 18.60 10 2 0 515.85 18.00 -10 2 0 542.05 18.40 -10 2 -1 1032.80 26.10 10 2 1 1022.70 25.60 10 2 2 226.18 12.50 -10 2 -2 244.28 13.30 10 2 3 126.99 9.70 -10 2 -3 127.99 10.00 -10 2 -4 156.58 11.30 -10 3 12 26.70 3.40 -10 3 11 97.39 6.10 10 3 -11 98.79 9.00 -10 3 10 67.29 5.30 10 3 -10 73.09 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6 9.40 3.50 -12 5 5 55.39 6.30 -12 5 4 79.59 7.80 -12 5 3 103.19 9.30 -12 5 2 293.67 15.60 -12 6 6 97.59 8.40 -12 6 5 80.49 8.10 -12 6 4 159.78 11.40 -12 6 3 220.28 13.50 13 -4 -8 353.16 15.50 13 -4 -7 37.70 5.80 13 -3 -10 75.79 7.60 13 -3 -9 209.08 11.80 13 -3 -8 23.80 4.50 -13 -3 8 29.90 5.90 13 -3 -7 353.76 15.90 -13 -3 7 425.36 19.00 13 -3 -6 614.14 21.40 -13 -3 6 627.84 23.00 -13 -3 5 34.90 6.20 -13 -3 4 29.80 6.00 -13 -3 3 1.40 3.10 -13 -2 11 104.69 9.70 13 -2 -11 98.49 8.40 -13 -2 10 468.85 19.90 13 -2 -10 471.45 17.90 13 -2 -9 46.50 6.20 -13 -2 9 51.39 7.00 -13 -2 8 52.99 6.90 13 -2 -8 57.99 6.60 -13 -2 7 30.30 5.40 13 -2 -7 40.00 5.70 13 -2 -6 81.09 8.00 -13 -2 6 81.89 8.40 -13 -2 5 4.90 3.80 -13 -2 4 194.78 12.50 -13 -2 3 107.29 9.80 -13 -2 2 27.70 5.40 -13 -2 1 429.96 19.60 -13 -1 13 48.20 7.20 -13 -1 12 6.30 3.80 13 -1 -12 7.30 4.30 -13 -1 11 20.50 4.80 13 -1 -11 13.00 4.40 -13 -1 10 702.53 23.40 13 -1 -10 693.33 22.30 -13 -1 9 236.08 13.50 13 -1 -9 238.48 13.20 -13 -1 8 135.69 10.30 13 -1 -8 135.99 10.10 13 -1 -7 66.49 7.20 -13 -1 7 74.09 8.10 13 -1 -6 375.76 16.80 -13 -1 6 369.76 16.80 -13 -1 5 73.59 7.90 -13 -1 4 79.19 8.20 -13 -1 3 236.58 14.10 -13 -1 2 58.59 7.20 -13 -1 1 66.29 7.80 -13 0 14 22.10 5.50 -13 0 13 10.00 4.90 -13 0 12 68.39 7.70 -13 0 11 147.99 10.60 -13 0 10 599.14 20.90 -13 0 9 48.70 6.40 13 0 -9 59.09 7.10 13 0 -8 20.60 4.70 -13 0 8 21.10 4.30 13 0 -7 -4.90 3.60 -13 0 7 5.00 2.90 13 0 -6 79.19 8.10 -13 0 6 79.79 7.90 -13 0 5 14.00 3.70 -13 0 4 405.76 17.80 -13 0 3 3.30 2.70 -13 0 2 41.10 6.30 -13 0 1 421.16 18.70 -13 1 13 66.69 7.50 -13 1 12 11.40 4.20 -13 1 11 22.60 4.90 -13 1 10 672.33 21.40 -13 1 9 218.28 12.30 -13 1 8 133.59 9.80 -13 1 7 69.39 7.50 -13 1 6 375.76 16.50 -13 1 5 77.39 7.80 -13 1 4 91.99 8.70 -13 1 3 228.48 13.70 -13 1 2 59.39 7.40 -13 1 1 61.29 7.80 -13 2 12 122.79 9.00 -13 2 11 114.69 9.00 -13 2 10 486.15 17.80 -13 2 9 54.09 6.40 -13 2 8 58.29 6.70 -13 2 7 42.70 5.80 -13 2 6 84.89 8.10 -13 2 5 4.40 3.20 -13 2 4 225.28 13.10 -13 2 3 109.59 9.40 -13 2 2 23.00 5.30 -13 2 1 432.56 19.20 -13 3 11 53.59 6.10 -13 3 10 73.79 7.30 -13 3 9 211.28 11.90 -13 3 8 22.50 4.20 -13 3 7 397.26 16.50 -13 3 6 670.83 21.90 -13 3 5 45.90 6.40 -13 3 4 27.70 5.30 -13 3 3 8.90 3.90 -13 3 2 24.90 5.30 -13 4 10 215.68 11.50 -13 4 9 126.69 9.10 -13 4 8 384.96 15.70 -13 4 7 42.40 5.70 -13 4 6 38.00 5.60 -13 4 5 123.49 9.80 -13 4 4 111.59 9.40 -13 4 3 765.82 25.20 -13 5 8 36.30 5.50 -13 5 7 72.59 7.70 -13 5 6 27.20 5.20 -13 5 5 16.90 4.80 -13 5 4 116.19 10.10 -14 -1 10 33.40 6.30 -14 -1 9 5.80 3.70 -14 -1 8 91.99 9.20 -14 -1 7 67.49 8.10 -14 -1 6 89.89 8.90 -14 -1 5 64.59 7.80 -14 0 12 -1.00 4.00 -14 0 11 11.30 4.10 -14 0 10 214.88 13.40 -14 0 9 282.77 15.20 -14 0 8 432.36 18.90 -14 0 7 455.25 19.30 -14 0 6 65.89 8.00 -14 0 5 59.29 7.70 -14 0 4 79.19 8.60 -14 1 12 19.40 5.30 -14 1 11 118.99 10.20 -14 1 10 42.90 6.30 -14 1 9 5.50 3.80 -14 1 8 97.19 9.00 -14 1 7 76.39 8.10 -14 1 6 110.19 9.70 -14 1 5 68.69 8.00 -14 1 4 236.78 14.50 -14 2 12 320.07 15.10 -14 2 11 224.08 12.90 -14 2 10 612.34 21.40 -14 2 9 346.37 16.20 -14 2 8 288.97 14.90 -14 2 7 515.45 20.00 -14 2 6 303.07 15.60 -14 2 5 14.50 4.30 -14 2 4 7.90 4.30 -14 3 10 105.39 9.00 -14 3 9 51.59 6.60 -14 3 8 13.70 4.70 -14 3 7 124.69 10.30 -14 3 6 74.89 8.00 -14 3 5 498.95 20.60 -14 4 9 18.30 4.70 -14 4 8 21.40 5.30 -14 4 7 120.89 10.00 -14 4 6 146.39 11.10 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT2014 (Sheldrick, 2015a)' _computing_cell_refinement 'CrysAlis PRO (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlis PRO (Rigaku OD, 2015)' _cell_measurement_reflns_used 4360 _cell_measurement_theta_min 2.7760 _cell_measurement_theta_max 29.4570 _exptl_absorpt_correction_T_min 0.98435 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ) CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ) _computing_data_collection ) Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014) MSCServDetCCD = {5.7.3.4} ) _diffrn_source 'Rotating Anode MicroMax-007HF DW 1.2 kW' _diffrn_measurement_device_type 'AFC11 (Right): Eulerian 3 circle CCD' _diffrn_measurement_method 'Profile data from \w-scans' _exptl_crystal_description plate _exptl_crystal_colour 'colourless' ; _shelx_hkl_checksum 35504 _shelx_res_file ; TITL (II)_a.res in P2(1) (II).res created by SHELXL-2018/3 at 13:25:39 on 27-Jul-2018 REM Old TITL (II) in P2(1) REM SHELXT solution in P2(1) REM R1 0.075, Rweak 0.027, Alpha 0.005, Orientation as input REM Flack x = 0.216 ( 0.037 ) from Parsons' quotients REM Formula found by SHELXT: C20 N O3 P CELL 0.71073 11.3482 7.3589 11.8714 90.000 113.686 90.000 ZERR 2.000 0.0003 0.0001 0.0003 0.000 0.003 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N O P UNIT 40 40 2 6 2 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 20 shel 999 0.83 temp -153 size 0.05 0.10 0.25 acta eqiv $1 -x+1, y+1/2, -z+1 eqiv $2 -x+2, y+1/2, -z+1 eqiv $3 x, y+1, z dfix 0.88 0.01 N1 H1N htab N1 O1_$1 htab C4 O1_$1 htab C7 O2_$2 htab C1 O2_$3 conf WGHT 0.046200 0.098200 FVAR 1.80253 P1 5 0.611508 0.342359 0.457314 11.00000 0.01501 0.01635 = 0.02192 0.00236 0.00863 0.00093 O1 4 0.497273 0.318784 0.484779 11.00000 0.01956 0.02328 = 0.03333 0.00631 0.01410 0.00042 O2 4 0.609759 0.240269 0.338596 11.00000 0.01966 0.01974 = 0.02630 -0.00321 0.00781 0.00150 O3 4 0.738839 0.242096 0.546382 11.00000 0.02201 0.02571 = 0.02475 0.00571 0.00992 0.00786 N1 3 0.639044 0.553911 0.444741 11.00000 0.02001 0.01546 = 0.03073 -0.00134 0.01684 -0.00007 H1N 2 0.595094 0.622696 0.474117 11.00000 -1.20000 C1 1 0.688995 0.790585 0.327932 11.00000 0.03901 0.02464 = 0.02658 0.00158 0.01402 -0.00572 AFIX 137 H1A 2 0.756472 0.840944 0.305358 11.00000 -1.50000 H1B 2 0.659169 0.884371 0.368949 11.00000 -1.50000 H1C 2 0.616759 0.749541 0.253623 11.00000 -1.50000 AFIX 0 C2 1 0.742922 0.629820 0.415044 11.00000 0.02274 0.01581 = 0.02806 -0.00222 0.01665 -0.00276 AFIX 13 H2 2 0.771108 0.534590 0.371076 11.00000 -1.20000 AFIX 0 C3 1 0.859042 0.687220 0.529004 11.00000 0.02196 0.01314 = 0.02829 0.00287 0.01428 -0.00002 C4 1 0.844017 0.785980 0.622167 11.00000 0.02041 0.02268 = 0.02810 0.00048 0.01188 0.00201 AFIX 43 H4 2 0.760075 0.816972 0.615132 11.00000 -1.20000 AFIX 0 C5 1 0.950427 0.839820 0.725423 11.00000 0.02721 0.02242 = 0.02618 -0.00001 0.01041 0.00005 AFIX 43 H5 2 0.939103 0.907449 0.788514 11.00000 -1.20000 AFIX 0 C6 1 1.073426 0.794732 0.736399 11.00000 0.02236 0.02369 = 0.03187 0.00516 0.00685 -0.00305 AFIX 43 H6 2 1.146384 0.830360 0.807278 11.00000 -1.20000 AFIX 0 C7 1 1.089154 0.697615 0.643526 11.00000 0.01906 0.02135 = 0.04603 0.00875 0.01639 0.00232 AFIX 43 H7 2 1.173247 0.667091 0.650786 11.00000 -1.20000 AFIX 0 C8 1 0.982984 0.644458 0.539835 11.00000 0.02583 0.01594 = 0.03845 0.00105 0.02050 -0.00108 AFIX 43 H8 2 0.994718 0.578894 0.476176 11.00000 -1.20000 AFIX 0 C9 1 0.508219 0.255317 0.222461 11.00000 0.02020 0.01965 = 0.02480 -0.00458 0.00868 0.00029 C10 1 0.395607 0.158420 0.197816 11.00000 0.03073 0.02696 = 0.03033 -0.00241 0.01229 -0.00793 AFIX 43 H10 2 0.383639 0.090261 0.260369 11.00000 -1.20000 AFIX 0 C11 1 0.300622 0.164140 0.078530 11.00000 0.02551 0.04423 = 0.03655 -0.00760 0.00713 -0.01109 AFIX 43 H11 2 0.222231 0.100206 0.059562 11.00000 -1.20000 AFIX 0 C12 1 0.319075 0.261302 -0.012063 11.00000 0.03418 0.04402 = 0.02394 -0.00685 0.00718 0.00026 AFIX 43 H12 2 0.253925 0.262478 -0.093213 11.00000 -1.20000 AFIX 0 C13 1 0.431818 0.357270 0.014199 11.00000 0.03917 0.03588 = 0.02744 -0.00043 0.01654 -0.00088 AFIX 43 H13 2 0.443778 0.424826 -0.048592 11.00000 -1.20000 AFIX 0 C14 1 0.527838 0.354640 0.132986 11.00000 0.02791 0.02535 = 0.02987 -0.00531 0.01549 -0.00516 AFIX 43 H14 2 0.605597 0.420236 0.152039 11.00000 -1.20000 AFIX 0 C15 1 0.784281 0.249787 0.674771 11.00000 0.02094 0.01944 = 0.02404 0.00333 0.00734 0.00489 C16 1 0.716099 0.165721 0.734055 11.00000 0.02170 0.02651 = 0.02947 0.00463 0.00889 0.00102 AFIX 43 H16 2 0.634913 0.111176 0.688400 11.00000 -1.20000 AFIX 0 C17 1 0.769014 0.162840 0.861875 11.00000 0.03709 0.03845 = 0.02975 0.00599 0.01673 0.00468 AFIX 43 H17 2 0.723324 0.106870 0.904333 11.00000 -1.20000 AFIX 0 C18 1 0.887770 0.240981 0.927550 11.00000 0.04000 0.03745 = 0.02532 -0.00219 0.00626 0.00778 AFIX 43 H18 2 0.924031 0.236838 1.014889 11.00000 -1.20000 AFIX 0 C19 1 0.953818 0.325067 0.866464 11.00000 0.02889 0.02445 = 0.03814 -0.00256 0.00181 -0.00090 AFIX 43 H19 2 1.034847 0.380043 0.912110 11.00000 -1.20000 AFIX 0 C20 1 0.902830 0.329809 0.739289 11.00000 0.02325 0.02204 = 0.03769 0.00552 0.01014 -0.00058 AFIX 43 H20 2 0.948318 0.386903 0.697044 11.00000 -1.20000 AFIX 0 HKLF 4 REM (II)_a.res in P2(1) REM wR2 = 0.0686, GooF = S = 1.055, Restrained GooF = 1.054 for all data REM R1 = 0.0252 for 2858 Fo > 4sig(Fo) and 0.0258 for all 2908 data REM 230 parameters refined using 2 restraints END WGHT 0.0462 0.0982 REM Highest difference peak 0.150, deepest hole -0.206, 1-sigma level 0.034 Q1 1 0.5795 0.3270 0.3543 11.00000 0.05 0.15 Q2 1 0.7093 0.6952 0.3545 11.00000 0.05 0.15 Q3 1 0.4595 0.1726 0.4358 11.00000 0.05 0.14 Q4 1 0.6609 0.4722 0.4986 11.00000 0.05 0.14 Q5 1 0.5165 0.3294 0.5519 11.00000 0.05 0.14 Q6 1 0.7384 0.2004 0.7927 11.00000 0.05 0.14 Q7 1 0.9181 0.8337 0.6758 11.00000 0.05 0.13 Q8 1 0.4931 0.3343 0.0788 11.00000 0.05 0.13 Q9 1 0.9104 0.3523 0.8032 11.00000 0.05 0.13 Q10 1 1.0319 0.6437 0.6071 11.00000 0.05 0.13 Q11 1 0.7224 0.2559 0.7042 11.00000 0.05 0.12 Q12 1 0.6706 0.3369 0.5795 11.00000 0.05 0.12 Q13 1 0.5810 0.4771 0.3840 11.00000 0.05 0.12 Q14 1 0.4841 0.1677 0.1999 11.00000 0.05 0.11 Q15 1 0.5031 0.3479 0.1750 11.00000 0.05 0.11 Q16 1 0.8430 0.3286 0.7165 11.00000 0.05 0.10 Q17 1 0.5239 0.4478 0.2530 11.00000 0.05 0.10 Q18 1 0.7202 0.0913 0.5220 11.00000 0.05 0.10 Q19 1 0.9218 1.0036 0.8082 11.00000 0.05 0.10 Q20 1 0.8557 0.7559 0.5640 11.00000 0.05 0.10 ; _shelx_res_checksum 55268 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 P P1 0.61151(4) 0.34236(6) 0.45731(4) 0.01737(14) Uani d 1 O O1 0.49727(12) 0.3188(2) 0.48478(13) 0.0243(3) Uani d 1 O O2 0.60976(12) 0.2403(2) 0.33860(13) 0.0224(3) Uani d 1 O O3 0.73884(13) 0.2421(2) 0.54638(13) 0.0240(3) Uani d 1 N N1 0.63904(16) 0.5539(2) 0.44474(16) 0.0199(4) Uani d 1 H H1N 0.595(2) 0.623(3) 0.4741(19) 0.024 Uiso d 1 C C1 0.6890(2) 0.7906(3) 0.3279(2) 0.0298(5) Uani d 1 H H1A 0.756472 0.840944 0.305358 0.045 Uiso calc 1 H H1B 0.659169 0.884371 0.368949 0.045 Uiso calc 1 H H1C 0.616759 0.749541 0.253623 0.045 Uiso calc 1 C C2 0.74292(18) 0.6298(3) 0.41504(18) 0.0201(4) Uani d 1 H H2 0.771108 0.534590 0.371076 0.024 Uiso calc 1 C C3 0.85904(18) 0.6872(3) 0.52900(18) 0.0198(4) Uani d 1 C C4 0.84402(18) 0.7860(3) 0.62217(18) 0.0230(5) Uani d 1 H H4 0.760075 0.816972 0.615132 0.028 Uiso calc 1 C C5 0.95043(18) 0.8398(4) 0.72542(17) 0.0254(4) Uani d 1 H H5 0.939103 0.907449 0.788514 0.030 Uiso calc 1 C C6 1.07343(19) 0.7947(3) 0.7364(2) 0.0273(5) Uani d 1 H H6 1.146384 0.830360 0.807278 0.033 Uiso calc 1 C C7 1.08915(19) 0.6976(3) 0.6435(2) 0.0278(5) Uani d 1 H H7 1.173247 0.667091 0.650786 0.033 Uiso calc 1 C C8 0.9830(2) 0.6445(3) 0.5398(2) 0.0243(4) Uani d 1 H H8 0.994718 0.578894 0.476176 0.029 Uiso calc 1 C C9 0.50822(18) 0.2553(3) 0.22246(18) 0.0217(4) Uani d 1 C C10 0.3956(2) 0.1584(3) 0.1978(2) 0.0293(5) Uani d 1 H H10 0.383639 0.090261 0.260369 0.035 Uiso calc 1 C C11 0.3006(2) 0.1641(4) 0.0785(2) 0.0371(6) Uani d 1 H H11 0.222231 0.100206 0.059562 0.045 Uiso calc 1 C C12 0.3191(2) 0.2613(4) -0.0121(2) 0.0355(5) Uani d 1 H H12 0.253925 0.262478 -0.093213 0.043 Uiso calc 1 C C13 0.4318(2) 0.3573(4) 0.01420(19) 0.0332(5) Uani d 1 H H13 0.443778 0.424826 -0.048592 0.040 Uiso calc 1 C C14 0.52784(19) 0.3546(4) 0.13299(18) 0.0265(4) Uani d 1 H H14 0.605597 0.420236 0.152039 0.032 Uiso calc 1 C C15 0.78428(18) 0.2498(3) 0.67477(18) 0.0220(4) Uani d 1 C C16 0.71610(19) 0.1657(3) 0.73405(19) 0.0263(5) Uani d 1 H H16 0.634913 0.111176 0.688400 0.032 Uiso calc 1 C C17 0.7690(2) 0.1628(4) 0.8619(2) 0.0340(5) Uani d 1 H H17 0.723324 0.106870 0.904333 0.041 Uiso calc 1 C C18 0.8878(2) 0.2410(4) 0.9276(2) 0.0364(6) Uani d 1 H H18 0.924031 0.236838 1.014889 0.044 Uiso calc 1 C C19 0.9538(2) 0.3251(4) 0.8665(2) 0.0342(5) Uani d 1 H H19 1.034847 0.380043 0.912110 0.041 Uiso calc 1 C C20 0.90283(18) 0.3298(3) 0.7393(2) 0.0283(5) Uani d 1 H H20 0.948318 0.386903 0.697044 0.034 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 P1 0.0150(2) 0.0164(3) 0.0219(2) 0.00093(19) 0.00863(17) 0.0024(2) O1 0.0196(6) 0.0233(9) 0.0333(7) 0.0004(6) 0.0141(5) 0.0063(7) O2 0.0197(7) 0.0197(8) 0.0263(7) 0.0015(6) 0.0078(5) -0.0032(6) O3 0.0220(7) 0.0257(9) 0.0247(7) 0.0079(6) 0.0099(6) 0.0057(7) N1 0.0200(8) 0.0155(9) 0.0307(9) -0.0001(7) 0.0168(7) -0.0013(8) C1 0.0390(12) 0.0246(13) 0.0266(10) -0.0057(9) 0.0140(9) 0.0016(9) C2 0.0227(10) 0.0158(11) 0.0281(10) -0.0028(7) 0.0167(8) -0.0022(9) C3 0.0220(9) 0.0131(10) 0.0283(10) 0.0000(7) 0.0143(8) 0.0029(8) C4 0.0204(9) 0.0227(12) 0.0281(10) 0.0020(7) 0.0119(8) 0.0005(9) C5 0.0272(9) 0.0224(11) 0.0262(9) 0.0000(10) 0.0104(8) 0.0000(11) C6 0.0224(10) 0.0237(13) 0.0319(10) -0.0030(8) 0.0068(8) 0.0052(9) C7 0.0191(9) 0.0214(12) 0.0460(12) 0.0023(8) 0.0164(9) 0.0088(10) C8 0.0258(10) 0.0159(11) 0.0384(11) -0.0011(8) 0.0205(9) 0.0010(10) C9 0.0202(9) 0.0196(10) 0.0248(9) 0.0003(8) 0.0087(8) -0.0046(9) C10 0.0307(11) 0.0270(13) 0.0303(11) -0.0079(9) 0.0123(9) -0.0024(10) C11 0.0255(11) 0.0442(16) 0.0365(12) -0.0111(10) 0.0071(9) -0.0076(12) C12 0.0342(12) 0.0440(15) 0.0239(10) 0.0003(11) 0.0072(9) -0.0069(11) C13 0.0392(12) 0.0359(15) 0.0274(10) -0.0009(11) 0.0165(9) -0.0004(12) C14 0.0279(10) 0.0253(12) 0.0299(10) -0.0052(9) 0.0155(8) -0.0053(11) C15 0.0209(9) 0.0194(11) 0.0240(9) 0.0049(8) 0.0073(8) 0.0033(9) C16 0.0217(10) 0.0265(12) 0.0295(10) 0.0010(9) 0.0089(8) 0.0046(10) C17 0.0371(12) 0.0384(15) 0.0297(11) 0.0047(11) 0.0167(10) 0.0060(11) C18 0.0400(13) 0.0374(15) 0.0253(11) 0.0078(11) 0.0063(10) -0.0022(11) C19 0.0289(10) 0.0244(12) 0.0381(11) -0.0009(10) 0.0018(8) -0.0026(11) C20 0.0232(9) 0.0220(11) 0.0377(11) -0.0006(9) 0.0101(8) 0.0055(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 '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 O1 P1 O3 116.45(8) O1 P1 O2 116.30(8) O3 P1 O2 93.13(8) O1 P1 N1 110.92(9) O3 P1 N1 110.68(9) O2 P1 N1 108.01(9) C9 O2 P1 123.17(12) C15 O3 P1 123.00(12) C2 N1 P1 126.53(14) C2 N1 H1N 121.1(17) P1 N1 H1N 111.1(17) C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 N1 C2 C3 112.58(15) N1 C2 C1 108.35(17) C3 C2 C1 110.81(18) N1 C2 H2 108.3 C3 C2 H2 108.3 C1 C2 H2 108.3 C4 C3 C8 119.06(18) C4 C3 C2 120.91(17) C8 C3 C2 120.02(18) C5 C4 C3 120.69(18) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 120.0(2) C4 C5 H5 120.0 C6 C5 H5 120.0 C7 C6 C5 119.7(2) C7 C6 H6 120.2 C5 C6 H6 120.2 C6 C7 C8 120.52(19) C6 C7 H7 119.7 C8 C7 H7 119.7 C7 C8 C3 120.1(2) C7 C8 H8 120.0 C3 C8 H8 120.0 C14 C9 C10 121.99(19) C14 C9 O2 118.44(17) C10 C9 O2 119.4(2) C9 C10 C11 118.0(2) C9 C10 H10 121.0 C11 C10 H10 121.0 C12 C11 C10 120.8(2) C12 C11 H11 119.6 C10 C11 H11 119.6 C11 C12 C13 120.4(2) C11 C12 H12 119.8 C13 C12 H12 119.8 C12 C13 C14 119.8(2) C12 C13 H13 120.1 C14 C13 H13 120.1 C9 C14 C13 119.0(2) C9 C14 H14 120.5 C13 C14 H14 120.5 C16 C15 C20 121.78(19) C16 C15 O3 119.93(18) C20 C15 O3 118.08(18) C15 C16 C17 118.5(2) C15 C16 H16 120.7 C17 C16 H16 120.7 C18 C17 C16 120.3(2) C18 C17 H17 119.8 C16 C17 H17 119.8 C19 C18 C17 120.1(2) C19 C18 H18 119.9 C17 C18 H18 119.9 C18 C19 C20 120.5(2) C18 C19 H19 119.8 C20 C19 H19 119.8 C19 C20 C15 118.7(2) C19 C20 H20 120.6 C15 C20 H20 120.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 O1 1.4685(13) P1 O3 1.5883(14) P1 O2 1.5902(14) P1 N1 1.6065(18) O2 C9 1.402(2) O3 C15 1.400(2) N1 C2 1.470(2) N1 H1N 0.875(12) C1 C2 1.528(3) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C2 C3 1.521(3) C2 H2 1.0000 C3 C4 1.390(3) C3 C8 1.396(3) C4 C5 1.389(3) C4 H4 0.9500 C5 C6 1.389(3) C5 H5 0.9500 C6 C7 1.384(3) C6 H6 0.9500 C7 C8 1.389(3) C7 H7 0.9500 C8 H8 0.9500 C9 C14 1.379(3) C9 C10 1.388(3) C10 C11 1.394(3) C10 H10 0.9500 C11 C12 1.376(4) C11 H11 0.9500 C12 C13 1.383(4) C12 H12 0.9500 C13 C14 1.393(3) C13 H13 0.9500 C14 H14 0.9500 C15 C16 1.384(3) C15 C20 1.384(3) C16 C17 1.390(3) C16 H16 0.9500 C17 C18 1.382(3) C17 H17 0.9500 C18 C19 1.381(4) C18 H18 0.9500 C19 C20 1.383(3) C19 H19 0.9500 C20 H20 0.9500 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 H1N O1 2_656 0.875(12) 1.957(14) 2.816(2) 167(2) yes C7 H7 O2 2_756 0.95 2.47 3.352(2) 153.7 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 O1 P1 O2 C9 51.71(18) O3 P1 O2 C9 173.36(16) N1 P1 O2 C9 -73.71(17) O1 P1 O3 C15 -47.47(19) O2 P1 O3 C15 -169.00(16) N1 P1 O3 C15 80.41(17) O1 P1 N1 C2 -178.52(16) O3 P1 N1 C2 50.63(19) O2 P1 N1 C2 -49.98(18) P1 N1 C2 C3 -96.9(2) P1 N1 C2 C1 140.17(17) N1 C2 C3 C4 -45.4(3) C1 C2 C3 C4 76.1(2) N1 C2 C3 C8 136.07(19) C1 C2 C3 C8 -102.4(2) C8 C3 C4 C5 -0.8(3) C2 C3 C4 C5 -179.3(2) C3 C4 C5 C6 -0.1(3) C4 C5 C6 C7 0.6(4) C5 C6 C7 C8 -0.2(3) C6 C7 C8 C3 -0.6(3) C4 C3 C8 C7 1.1(3) C2 C3 C8 C7 179.65(19) P1 O2 C9 C14 107.7(2) P1 O2 C9 C10 -77.6(2) C14 C9 C10 C11 -0.2(4) O2 C9 C10 C11 -174.7(2) C9 C10 C11 C12 0.8(4) C10 C11 C12 C13 -0.9(4) C11 C12 C13 C14 0.4(4) C10 C9 C14 C13 -0.2(3) O2 C9 C14 C13 174.3(2) C12 C13 C14 C9 0.1(4) P1 O3 C15 C16 68.2(3) P1 O3 C15 C20 -117.05(19) C20 C15 C16 C17 0.1(3) O3 C15 C16 C17 174.7(2) C15 C16 C17 C18 -0.6(4) C16 C17 C18 C19 1.0(4) C17 C18 C19 C20 -0.9(4) C18 C19 C20 C15 0.4(4) C16 C15 C20 C19 0.0(4) O3 C15 C20 C19 -174.7(2) _cod_database_fobs_code 2021472