#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:06:13 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253827 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126514.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_7126514 loop_ _publ_author_name 'Fujii, Toshiki' 'Tanaka, Susumu' 'Hayashi, Shotaro' 'Imoto, Hiroaki' 'Naka, Kensuke' _publ_section_title ; Dipyridinoarsole: a new class of stable and modifiable heteroatom-bridged bipyridines. ; _journal_issue 45 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6035 _journal_page_last 6038 _journal_paper_doi 10.1039/d0cc02389b _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C16 H11 N2 O P' _chemical_formula_sum 'C16 H11 N2 O P' _chemical_formula_weight 278.25 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2020-04-02 deposited with the CCDC. 2020-05-11 downloaded from the CCDC. ; _cell_angle_alpha 88.33(2) _cell_angle_beta 72.47(2) _cell_angle_gamma 67.903(14) _cell_formula_units_Z 2 _cell_length_a 7.692(4) _cell_length_b 9.588(6) _cell_length_c 10.081(7) _cell_measurement_reflns_used 1666 _cell_measurement_temperature 273 _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 7.74 _cell_volume 653.9(7) _computing_cell_refinement DTREK _computing_data_collection DTREK _computing_data_reduction DTREK _computing_molecular_graphics 'CrystalStructure 4.1' _computing_publication_material 'CrystalStructure 4.1 (Rigaku, 2014)' _computing_structure_refinement 'SHELXL2013 (Sheldrick, 2008)' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _diffrn_ambient_temperature 273 _diffrn_detector_area_resol_mean 13.653 _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.972 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6758 _diffrn_reflns_point_group_measured_fraction_full 0.969 _diffrn_reflns_point_group_measured_fraction_max 0.972 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.525 _diffrn_reflns_theta_min 7.705 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_description chip _exptl_crystal_F_000 288.00 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.31 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 181 _refine_ls_number_reflns 2925 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0411 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1418P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1027 _refine_ls_wR_factor_ref 0.1105 _reflns_number_gt 2415 _reflns_number_total 2925 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d0cc02389b2.cif _cod_data_source_block DPP-Ox_6 _cod_depositor_comments 'Adding full bibliography for 7126511--7126515.cif.' _cod_database_code 7126514 _shelxl_res_file ; shelxl.res created by SHELXL-2014/7 TITL Dipyridinophosphole-Oxide_02 CELL 0.71075 7.69160 9.58850 10.08060 88.32970 72.46800 67.90300 ZERR 2 0.00424 0.00640 0.00655 0.02130 0.02040 0.01400 LATT 1 SFAC C H N O P UNIT 32 22 4 2 2 L.S. 5 FMAP 2 PLAN -25 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP 0.0 ACTA SIZE 0.280 0.260 0.150 WGHT 0.057700 0.141800 FVAR 3.95268 P1 5 0.469524 0.863436 0.713039 11.00000 0.03543 0.03382 = 0.03421 0.00791 -0.01043 -0.01132 O1 4 0.653578 0.865228 0.611980 11.00000 0.03922 0.06046 = 0.04707 0.01188 -0.00752 -0.02093 N5 3 0.592468 0.630424 1.046766 11.00000 0.05765 0.04163 = 0.05006 0.01510 -0.02611 -0.01079 N19 3 0.044110 1.298221 0.812253 11.00000 0.05245 0.03298 = 0.06353 0.01346 -0.02304 -0.01027 C1 1 0.278940 1.044100 0.794894 11.00000 0.03667 0.03088 = 0.03969 0.00809 -0.01380 -0.01356 C2 1 0.348417 0.767498 0.646080 11.00000 0.03556 0.03400 = 0.03173 0.00281 -0.00483 -0.01058 C3 1 0.480736 0.797060 0.881501 11.00000 0.03946 0.03344 = 0.03772 0.00807 -0.01496 -0.01144 C6 1 0.185197 1.172128 0.735271 11.00000 0.04874 0.03639 = 0.04722 0.01399 -0.02031 -0.01680 AFIX 43 H6 2 0.221772 1.170171 0.638387 11.00000 -1.20000 AFIX 0 C7 1 0.082362 1.177526 1.021169 11.00000 0.04519 0.03659 = 0.04511 0.00356 -0.00827 -0.01142 AFIX 43 H7 2 0.044329 1.183620 1.118261 11.00000 -1.20000 AFIX 0 C8 1 0.602423 0.661175 0.915068 11.00000 0.04687 0.03536 = 0.04858 0.00621 -0.01891 -0.00549 AFIX 43 H8 2 0.694655 0.588608 0.842804 11.00000 -1.20000 AFIX 0 C9 1 0.333270 0.876943 1.127355 11.00000 0.05262 0.04073 = 0.03636 0.00546 -0.01274 -0.01533 AFIX 43 H9 2 0.244602 0.947530 1.202197 11.00000 -1.20000 AFIX 0 C10 1 0.254971 0.835507 0.548270 11.00000 0.05559 0.04744 = 0.05273 0.01578 -0.02424 -0.02349 AFIX 43 H10 2 0.262667 0.925537 0.516019 11.00000 -1.20000 AFIX 0 C11 1 0.339485 0.631086 0.690208 11.00000 0.06312 0.03690 = 0.05081 0.01011 -0.01744 -0.01873 AFIX 43 H11 2 0.402845 0.583273 0.754011 11.00000 -1.20000 AFIX 0 C12 1 -0.004425 1.298334 0.951628 11.00000 0.04836 0.03222 = 0.06133 0.00447 -0.01231 -0.00474 AFIX 43 H12 2 -0.102842 1.385138 1.005434 11.00000 -1.20000 AFIX 0 C13 1 0.460634 0.737393 1.147978 11.00000 0.06296 0.04773 = 0.04250 0.01641 -0.02339 -0.01834 AFIX 43 H13 2 0.453726 0.716576 1.239684 11.00000 -1.20000 AFIX 0 C14 1 0.151519 0.770385 0.499165 11.00000 0.06220 0.06939 = 0.07016 0.01310 -0.03573 -0.03047 AFIX 43 H14 2 0.087847 0.817274 0.435235 11.00000 -1.20000 AFIX 0 C15 1 0.236100 0.566191 0.639132 11.00000 0.08742 0.04868 = 0.07754 0.01249 -0.02366 -0.04002 AFIX 43 H15 2 0.230229 0.474917 0.669014 11.00000 -1.20000 AFIX 0 C16 1 0.142464 0.635652 0.544878 11.00000 0.06601 0.07055 = 0.08520 -0.00163 -0.02566 -0.04073 AFIX 43 H16 2 0.072613 0.591723 0.511678 11.00000 -1.20000 AFIX 0 C17 1 0.226914 1.048212 0.941194 11.00000 0.03601 0.03089 = 0.04053 0.00741 -0.01298 -0.01312 C18 1 0.343225 0.907282 0.990469 11.00000 0.03751 0.03197 = 0.03888 0.00836 -0.01376 -0.01400 HKLF 4 REM Dipyridinophosphole-Oxide_02 REM R1 = 0.0411 for 2415 Fo > 4sig(Fo) and 0.0523 for all 2925 data REM 181 parameters refined using 0 restraints END WGHT 0.0575 0.1421 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+2, -z+1 HTAB C6 O1_$1 HTAB C10 O1_$1 EQIV $2 x-1, y+1, z HTAB C12 N5_$2 REM Highest difference peak 0.313, deepest hole -0.213, 1-sigma level 0.042 Q1 1 0.3599 0.9624 0.7602 11.00000 0.05 0.31 Q2 1 0.3949 0.8211 0.6782 11.00000 0.05 0.29 Q3 1 0.4708 0.8201 0.8107 11.00000 0.05 0.26 Q4 1 0.5079 0.7357 0.8976 11.00000 0.05 0.23 Q5 1 0.2845 0.9827 0.9647 11.00000 0.05 0.20 Q6 1 0.4134 0.8542 0.9409 11.00000 0.05 0.20 Q7 1 0.2332 1.0876 0.7779 11.00000 0.05 0.20 Q8 1 0.1520 1.1082 0.9787 11.00000 0.05 0.19 Q9 1 0.2535 1.0487 0.8550 11.00000 0.05 0.18 Q10 1 0.2869 0.6013 0.6574 11.00000 0.05 0.17 Q11 1 0.3832 0.8055 1.1387 11.00000 0.05 0.16 Q12 1 0.1083 0.7405 0.5657 11.00000 0.05 0.16 Q13 1 0.4759 0.6819 1.0953 11.00000 0.05 0.16 Q14 1 0.3232 0.8802 1.0599 11.00000 0.05 0.16 Q15 1 0.2058 0.6961 0.4806 11.00000 0.05 0.15 Q16 1 0.4146 0.5831 1.1404 11.00000 0.05 0.15 Q17 1 0.2457 0.7861 0.5114 11.00000 0.05 0.15 Q18 1 0.2924 0.8060 0.6277 11.00000 0.05 0.15 Q19 1 0.1104 1.2330 0.7828 11.00000 0.05 0.15 Q20 1 0.3455 0.7857 0.5848 11.00000 0.05 0.15 Q21 1 0.0333 0.9777 0.7646 11.00000 0.05 0.14 Q22 1 0.1795 0.7595 0.3598 11.00000 0.05 0.14 Q23 1 0.0195 1.2247 0.9893 11.00000 0.05 0.14 Q24 1 0.1331 0.7772 0.4727 11.00000 0.05 0.13 Q25 1 0.0050 0.9256 0.4459 11.00000 0.05 0.13 ; _shelxl_hkl_file ; 0 0 4 897.06 32.42 0 0 -4 884.31 35.03 0 0 -4 901.55 27.34 0 0 5 1433.03 47.27 0 0 -5 1440.83 51.99 0 0 -5 1368.96 38.03 0 0 6 349.76 24.72 0 0 -6 346.77 24.08 0 0 -6 350.85 17.71 0 0 7 785.62 44.19 0 0 -7 750.72 39.78 0 0 -7 765.09 23.99 0 0 8 3.82 25.49 0 0 -8 -8.32 18.03 0 0 -8 21.85 10.05 0 0 9 747.74 44.32 0 0 -9 769.26 44.71 0 0 10 38.50 21.18 0 0 -10 97.79 19.75 0 0 11 109.36 36.92 0 0 -11 83.41 28.30 0 0 12 842.37 58.51 0 0 -12 929.52 65.95 0 1 -12 -11.67 20.65 0 -1 12 26.74 24.96 0 1 -11 1105.10 61.07 0 -1 11 1104.29 59.02 0 1 -10 69.41 29.93 0 -1 10 65.17 25.44 0 1 -9 499.98 38.30 0 1 -9 502.61 23.68 0 -1 9 468.98 31.80 0 1 -8 180.83 26.46 0 1 -8 171.03 16.25 0 -1 8 145.54 24.85 0 1 -7 811.68 40.74 0 1 -7 759.32 25.79 0 -1 7 821.20 118.31 0 1 -6 5340.63 91.73 0 1 -6 5373.46 76.75 0 -1 6 5504.53 88.28 0 1 -5 -3.73 13.45 0 1 -5 15.82 9.71 0 -1 5 8.17 6.75 0 1 -411183.87 94.53 0 1 4 329.90 20.56 0 -1 -4 385.26 23.41 0 -1 -4 387.28 17.03 0 1 5 35.03 14.81 0 -1 -5 57.08 14.37 0 -1 -5 60.38 9.32 0 1 6 1842.00 59.13 0 -1 -6 1687.71 51.07 0 -1 -6 1728.05 35.48 0 1 7 2287.79 61.60 0 -1 -7 2255.51 57.75 0 -1 -7 2281.35 39.15 0 1 8 386.49 45.19 0 -1 -8 263.36 27.27 0 -1 -8 312.93 17.92 0 1 9 -21.49 25.60 0 -1 -9 -26.51 18.45 0 1 10 727.73 47.56 0 -1 -10 725.31 47.16 0 1 11 206.34 42.03 0 -1 -11 337.06 44.66 0 1 12 967.91 79.27 0 -1 -12 831.33 62.20 0 2 -12 149.10 29.29 0 -2 12 82.17 32.10 0 2 -11 539.27 49.72 0 -2 11 473.46 35.51 0 2 -10 26.81 16.10 0 -2 10 50.62 14.47 0 2 -9 52.01 20.86 0 2 -9 57.47 13.45 0 -2 9 21.20 16.38 0 2 -8 2119.51 74.15 0 2 -8 2102.89 61.56 0 -2 8 2121.81 84.70 0 2 -7 -13.63 16.77 0 2 -7 15.43 8.92 0 -2 7 17.52 13.16 0 2 -6 78.34 19.53 0 2 -6 104.20 14.02 0 -2 6 98.50 20.05 0 2 -5 6477.53 76.83 0 2 -5 6708.63 65.64 0 -2 5 6890.33 82.43 0 2 -4 3036.33 41.44 0 2 3 681.90 33.50 0 -2 -3 671.00 24.19 0 -2 -3 674.41 23.88 0 2 4 352.18 31.82 0 -2 -4 275.43 19.31 0 -2 -4 309.72 19.60 0 2 5 -23.10 24.36 0 -2 -5 -7.10 12.60 0 -2 -5 -1.68 9.58 0 2 6 425.48 42.24 0 -2 -6 381.01 26.90 0 -2 -6 396.09 20.81 0 2 7 955.97 52.40 0 -2 -7 946.25 40.90 0 -2 -7 943.95 26.87 0 2 8 4878.92 115.75 0 -2 -8 5142.77 116.87 0 -2 -8 4761.73 89.02 0 2 9 -2.15 24.03 0 -2 -9 5.84 16.47 0 2 10 257.60 35.73 0 -2 -10 247.52 32.55 0 2 11 709.32 54.42 0 -2 -11 748.58 52.65 0 -2 -12 45.70 21.50 0 3 -12 190.35 35.68 0 3 -11 18.49 16.88 0 -3 11 58.47 24.81 0 3 -10 1079.82 53.08 0 3 -10 901.56 36.21 0 -3 10 850.28 142.42 0 3 -9 -1.23 16.78 0 3 -9 -2.55 9.17 0 -3 9 -0.16 8.01 0 3 -8 161.02 26.03 0 3 -8 149.97 17.36 0 -3 8 163.67 31.61 0 3 -7 4311.22 78.43 0 3 -7 4214.14 65.57 0 3 -6 689.39 33.74 0 3 -6 675.35 28.39 0 -3 6 722.55 105.13 0 3 -5 1392.62 38.81 0 3 -5 1408.98 34.75 0 3 -5 1487.56 38.19 0 3 -4 40.13 11.49 0 3 -4 43.21 13.49 0 3 -4 33.89 10.31 0 3 -310533.76 81.58 0 3 -310736.58 89.65 0 3 -310595.46 83.83 0 3 -2 1213.08 38.46 0 3 -2 1268.72 37.38 0 -3 2 1286.65 36.19 0 3 213773.89 108.30 0 -3 -213716.74 90.01 0 -3 -213985.00 102.91 0 3 3 378.98 28.23 0 -3 -3 309.97 18.99 0 -3 -3 325.62 19.55 0 3 4 75.16 18.39 0 -3 -4 55.89 11.72 0 -3 -4 61.33 11.55 0 3 5 754.18 45.05 0 -3 -5 746.14 31.65 0 -3 -5 741.74 27.67 0 3 6 869.56 49.46 0 -3 -6 850.08 37.75 0 -3 -6 834.40 29.33 0 3 7 5086.25 108.97 0 -3 -7 5126.10 98.53 0 -3 -7 5135.71 84.32 0 3 8 5684.59 128.34 0 -3 -8 5775.31 91.69 0 3 9 291.59 48.75 0 -3 -9 266.05 34.10 0 3 10 11.47 29.07 0 -3 -10 27.05 16.70 0 3 11 426.45 48.23 0 -3 -11 387.31 41.24 0 4 -12 380.43 49.98 0 4 -11 508.92 46.38 0 -4 11 405.00 84.69 0 4 -10 714.42 58.33 0 4 -10 656.39 44.23 0 -4 10 659.83 85.61 0 4 -9 335.39 29.84 0 4 -9 361.72 26.14 0 -4 9 334.87 74.65 0 4 -8 74.17 21.08 0 4 -8 18.47 14.48 0 -4 8 41.48 13.82 0 4 -7 9483.11 149.68 0 4 -710058.70 151.32 0 -4 710122.36 151.00 0 4 -6 17.48 13.99 0 4 -6 -4.61 10.62 0 4 -6 7.35 12.37 0 4 -5 2238.54 52.71 0 4 -5 2186.76 52.63 0 4 -5 2101.56 49.00 0 4 -4 1202.75 31.45 0 4 -4 1145.73 34.40 0 4 -4 1204.39 31.85 0 4 -323647.88 162.62 0 4 -323874.22 156.10 0 -4 323318.91 145.94 0 4 -2 1741.60 53.57 0 4 -2 1824.08 52.26 0 -4 2 1902.08 50.42 0 4 -110842.28 89.78 0 -4 110834.27 70.72 0 -4 020399.82 143.37 0 -4 -113780.95 86.08 0 -4 -113848.19 128.03 0 4 2 1264.74 47.78 0 -4 -2 1234.84 36.67 0 -4 -2 1306.56 68.79 0 4 3 2102.28 48.73 0 -4 -3 2044.68 35.92 0 -4 -3 2140.87 41.21 0 4 4 1476.02 47.59 0 -4 -4 1524.62 42.22 0 -4 -4 1441.80 41.28 0 4 5 1259.32 48.96 0 -4 -5 1133.91 40.88 0 -4 -5 1215.56 38.86 0 4 6 2235.54 69.79 0 -4 -6 2400.26 64.07 0 -4 -6 2266.20 53.30 0 4 7 750.43 45.74 0 -4 -7 907.62 47.00 0 -4 -7 854.49 35.26 0 4 8 152.17 42.99 0 -4 -8 178.43 25.54 0 -4 -8 137.32 16.62 0 4 9 290.91 45.67 0 -4 -9 306.46 35.71 0 4 10 328.42 51.63 0 -4 -10 362.77 42.18 0 4 11 55.22 27.69 0 -4 -11 -18.83 17.64 0 5 -11 609.56 56.83 0 5 -10 38.40 22.57 0 5 -10 9.15 13.28 0 -5 10 24.26 9.40 0 5 -9 2728.08 159.68 0 5 -9 2495.06 143.05 0 -5 9 2847.83 167.83 0 5 -8 347.86 29.13 0 5 -8 339.98 29.10 0 -5 8 294.95 65.68 0 5 -7 1543.15 60.34 0 5 -7 1622.02 53.53 0 5 -7 1601.70 56.98 0 5 -6 1408.56 48.11 0 5 -6 1436.18 46.61 0 5 -6 1398.59 45.02 0 5 -5 3226.97 66.67 0 5 -5 3249.97 60.11 0 -5 5 3374.73 60.95 0 5 -4 63.65 16.24 0 5 -4 62.90 13.01 0 -5 4 72.92 15.32 0 5 -3 46.00 21.44 0 5 -3 37.66 12.16 0 -5 3 45.38 12.36 0 5 -2 809.72 34.77 0 5 -2 859.03 31.93 0 -5 2 747.54 18.80 0 5 -116429.80 123.17 0 -5 116277.19 93.41 0 5 0 -1.87 13.59 0 -5 0 -0.05 4.58 0 -5 0 -1.06 5.79 0 5 1 1556.46 43.75 0 -5 -1 1533.97 25.23 0 -5 -1 1626.49 72.54 0 5 2 248.78 24.19 0 -5 -2 321.12 17.06 0 -5 -2 311.35 46.24 0 5 3 31.50 30.07 0 -5 -3 21.06 7.90 0 -5 -3 45.37 20.41 0 5 4 47.70 26.52 0 -5 -4 41.67 10.41 0 -5 -4 57.18 16.68 0 5 5 667.49 39.84 0 -5 -5 676.29 31.16 0 -5 -5 660.25 31.85 0 5 6 633.54 43.53 0 -5 -6 757.61 36.81 0 -5 -6 654.52 31.88 0 5 7 9.82 26.64 0 -5 -7 7.70 12.05 0 -5 -7 22.83 16.65 0 5 8 555.35 51.32 0 -5 -8 629.64 52.80 0 5 9 204.53 34.48 0 -5 -9 123.77 27.22 0 5 10 470.35 52.51 0 -5 -10 545.61 52.36 0 -6 11 14.52 16.23 0 6 -10 1239.13 53.58 0 -6 10 893.06 163.01 0 6 -9 62.62 18.60 0 -6 9 36.41 14.82 0 -6 9 21.87 9.73 0 6 -8 2643.36 67.38 0 6 -8 2595.26 66.69 0 -6 8 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1 0 930.03 69.30 9 1 1 60.09 31.39 9 1 2 298.45 45.89 9 1 3 369.00 50.80 -9 -1 -3 410.54 43.56 9 1 4 581.88 60.33 -9 -1 -4 519.21 48.50 9 1 5 29.31 26.08 -9 -1 -5 82.56 30.90 9 1 6 233.03 37.06 -9 -1 -6 296.05 38.79 9 1 7 341.09 48.69 -9 -1 -7 354.86 47.33 9 1 8 45.11 26.28 9 2 -1 69.53 26.14 -9 -2 1 93.08 27.78 9 2 0 425.81 52.01 -9 -2 0 320.58 38.09 9 2 1 8.45 20.65 9 2 2 25.24 20.90 9 2 3 8.05 21.01 -9 -2 -3 68.31 32.37 9 2 4 488.56 45.19 -9 -2 -4 463.50 41.22 9 2 5 512.80 44.94 -9 -2 -5 521.14 42.85 9 2 6 13.17 20.63 -9 -2 -6 -2.94 20.50 9 2 7 655.86 55.26 -9 -2 -7 642.54 51.08 9 2 8 67.04 37.27 -9 -2 -8 72.49 32.11 9 3 -1 218.37 40.15 -9 -3 1 206.84 32.77 9 3 0 82.70 38.67 -9 -3 0 23.37 18.46 9 3 1 245.56 44.48 -9 -3 -1 106.88 24.27 9 3 2 -1.73 21.82 -9 -3 -2 7.45 15.92 9 3 3 298.21 38.23 -9 -3 -3 298.14 28.72 9 3 4 38.48 35.38 -9 -3 -4 34.05 30.49 9 3 5 276.89 47.47 -9 -3 -5 216.43 28.89 9 3 6 49.15 30.29 -9 -3 -6 92.90 32.16 9 3 7 8.41 24.61 -9 -3 -7 58.79 33.05 9 3 8 708.72 56.89 -9 -3 -8 664.65 56.87 9 4 -1 181.53 33.75 -9 -4 1 142.06 29.17 9 4 0 549.20 54.97 -9 -4 0 350.18 76.49 9 4 1 90.52 27.78 -9 -4 -1 39.43 18.15 9 4 2 114.17 30.22 -9 -4 -2 111.69 23.55 -9 -4 -2 87.39 13.77 9 4 3 433.82 41.93 -9 -4 -3 423.97 36.62 9 4 4 -7.40 19.85 -9 -4 -4 19.39 20.46 9 4 5 -27.72 18.24 -9 -4 -5 12.88 29.46 9 4 6 438.99 43.13 -9 -4 -6 418.78 38.54 9 4 7 431.44 52.52 -9 -4 -7 450.76 46.93 9 4 8 218.89 42.11 -9 -4 -8 265.22 36.72 9 4 9 60.01 32.33 9 5 -1 16.55 19.60 -9 -5 1 27.39 17.42 9 5 0 597.42 55.21 -9 -5 0 479.99 87.79 9 5 1 89.43 26.42 -9 -5 -1 32.93 15.83 9 5 2 -4.09 17.57 -9 -5 -2 -1.72 16.57 -9 -5 -2 28.18 12.80 9 5 3 27.70 26.51 -9 -5 -3 32.09 20.22 9 5 4 394.02 37.81 -9 -5 -4 505.60 44.79 9 5 5 269.50 36.27 -9 -5 -5 275.68 43.12 9 5 6 124.53 27.37 -9 -5 -6 69.87 30.25 9 5 7 755.42 65.38 -9 -5 -7 798.22 69.72 9 5 8 95.48 36.34 -9 -5 -8 118.19 32.49 9 6 -1 34.96 18.80 -9 -6 1 32.64 17.56 9 6 0 58.21 30.58 -9 -6 0 70.78 16.71 9 6 1 -0.63 15.70 -9 -6 -1 7.60 16.92 -9 -6 -1 2.79 8.48 9 6 2 167.47 32.91 -9 -6 -2 145.04 29.68 -9 -6 -2 74.15 27.00 9 6 3 131.15 31.79 -9 -6 -3 163.18 34.73 -9 -6 -3 68.10 23.96 9 6 4 38.57 23.36 -9 -6 -4 90.83 27.05 9 6 5 303.55 38.39 -9 -6 -5 407.22 46.30 -9 -6 -6 102.29 36.47 9 6 7 132.50 27.77 -9 -6 -7 144.70 36.08 9 6 8 58.45 21.20 -9 -6 -8 112.44 34.15 9 7 -1 56.02 23.70 -9 -7 1 42.20 15.31 9 7 0 23.35 17.83 -9 -7 0 30.68 16.26 9 7 1 70.19 22.34 -9 -7 -1 35.10 28.25 -9 -7 -1 48.47 20.51 9 7 2 23.61 18.21 9 7 2 30.30 19.22 -9 -7 -2 -3.13 20.71 9 7 3 122.53 25.76 9 7 3 172.80 28.59 -9 -7 -3 150.54 38.24 9 7 4 301.28 34.41 -9 -7 -4 246.79 36.21 9 7 5 163.00 32.46 -9 -7 -5 114.49 34.29 9 7 6 272.30 33.67 -9 -7 -6 268.88 38.40 -9 -7 -7 -3.89 24.78 -9 -8 0 61.67 19.99 9 8 1 -3.71 17.10 -9 -8 -1 -2.26 20.60 9 8 2 1160.29 56.37 -9 -8 -2 1283.21 66.42 9 8 3 62.16 20.87 -9 -8 -4 305.20 41.58 -9 -8 -5 8.19 27.29 -9 -8 -6 299.81 45.06 9 9 2 167.49 30.23 -9 -9 -2 136.20 37.12 9 9 3 19.16 17.25 -9 -9 -3 39.00 25.95 9 9 4 170.24 32.33 -9 -9 -4 161.53 38.66 ; loop_ _symmetry_equiv_pos_site_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-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_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.46952(6) 0.86344(4) 0.71304(4) 0.03533(15) Uani 1 2 d . . . O1 O 0.65358(17) 0.86523(15) 0.61198(13) 0.0500(3) Uani 1 2 d . . . N1 N 0.5925(2) 0.63042(17) 1.04677(17) 0.0504(4) Uani 1 2 d . . . N2 N 0.0441(2) 1.29822(16) 0.81225(18) 0.0506(4) Uani 1 2 d . . . C1 C 0.4807(2) 0.79706(17) 0.88150(16) 0.0371(3) Uani 1 2 d . . . C2 C 0.3432(2) 0.90728(17) 0.99047(17) 0.0356(3) Uani 1 2 d . . . C3 C 0.2269(2) 1.04821(17) 0.94119(17) 0.0356(3) Uani 1 2 d . . . C4 C 0.2789(2) 1.04410(17) 0.79489(17) 0.0352(3) Uani 1 2 d . . . C5 C 0.3484(2) 0.76750(17) 0.64608(16) 0.0360(3) Uani 1 2 d . . . C6 C 0.6024(3) 0.66118(19) 0.91507(19) 0.0459(4) Uani 1 2 d . . . C7 C 0.4606(3) 0.7374(2) 1.1480(2) 0.0506(4) Uani 1 2 d . . . C8 C 0.3333(3) 0.8769(2) 1.12735(18) 0.0444(4) Uani 1 2 d . . . C9 C 0.1852(3) 1.17213(18) 0.73527(19) 0.0429(4) Uani 1 2 d . . . C10 C -0.0044(3) 1.29833(19) 0.9516(2) 0.0518(5) Uani 1 2 d . . . C11 C 0.0824(3) 1.17753(19) 1.02117(19) 0.0450(4) Uani 1 2 d . . . C12 C 0.3395(3) 0.6311(2) 0.6902(2) 0.0507(4) Uani 1 2 d . . . C13 C 0.2361(4) 0.5662(3) 0.6391(3) 0.0676(6) Uani 1 2 d . . . C14 C 0.1425(4) 0.6357(3) 0.5449(3) 0.0688(6) Uani 1 2 d . . . C15 C 0.1515(3) 0.7704(3) 0.4992(3) 0.0622(5) Uani 1 2 d . . . C16 C 0.2550(3) 0.8355(2) 0.5483(2) 0.0493(4) Uani 1 2 d . . . H6 H 0.69466 0.58861 0.8428 0.0551 Uiso 1 2 calc R . . H7 H 0.45373 0.71658 1.23968 0.0607 Uiso 1 2 calc R . . H8 H 0.2446 0.94753 1.2022 0.0533 Uiso 1 2 calc R . . H9 H 0.22177 1.17017 0.63839 0.0515 Uiso 1 2 calc R . . H10 H -0.10284 1.38514 1.00543 0.0622 Uiso 1 2 calc R . . H11 H 0.04433 1.18362 1.11826 0.0541 Uiso 1 2 calc R . . H12 H 0.40284 0.58327 0.75401 0.0608 Uiso 1 2 calc R . . H13 H 0.23023 0.47492 0.66901 0.0811 Uiso 1 2 calc R . . H14 H 0.07261 0.59172 0.51168 0.0825 Uiso 1 2 calc R . . H15 H 0.08785 0.81727 0.43524 0.0746 Uiso 1 2 calc R . . H16 H 0.26267 0.92554 0.51602 0.0591 Uiso 1 2 calc R . . 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 0.0354(2) 0.0338(2) 0.0342(2) -0.01132(16) -0.01043(17) 0.00791(15) O1 0.0392(7) 0.0605(8) 0.0471(7) -0.0209(6) -0.0075(6) 0.0119(6) N1 0.0577(9) 0.0416(8) 0.0501(9) -0.0108(7) -0.0261(8) 0.0151(7) N2 0.0524(9) 0.0330(7) 0.0635(10) -0.0103(6) -0.0230(8) 0.0135(7) C1 0.0395(8) 0.0334(8) 0.0377(8) -0.0114(6) -0.0150(7) 0.0081(6) C2 0.0375(8) 0.0320(7) 0.0389(8) -0.0140(6) -0.0138(7) 0.0084(6) C3 0.0360(8) 0.0309(7) 0.0405(8) -0.0131(6) -0.0130(7) 0.0074(6) C4 0.0367(8) 0.0309(7) 0.0397(8) -0.0136(6) -0.0138(7) 0.0081(6) C5 0.0356(8) 0.0340(8) 0.0317(7) -0.0106(6) -0.0048(6) 0.0028(6) C6 0.0469(10) 0.0354(8) 0.0486(10) -0.0055(7) -0.0189(8) 0.0062(7) C7 0.0630(12) 0.0477(10) 0.0425(9) -0.0183(9) -0.0234(9) 0.0164(8) C8 0.0526(10) 0.0407(9) 0.0364(8) -0.0153(7) -0.0127(8) 0.0055(7) C9 0.0487(9) 0.0364(8) 0.0472(9) -0.0168(7) -0.0203(8) 0.0140(7) C10 0.0484(10) 0.0322(8) 0.0613(12) -0.0047(7) -0.0123(9) 0.0045(8) C11 0.0452(9) 0.0366(8) 0.0451(9) -0.0114(7) -0.0083(8) 0.0036(7) C12 0.0631(12) 0.0369(9) 0.0508(10) -0.0187(8) -0.0174(9) 0.0101(7) C13 0.0874(16) 0.0487(11) 0.0775(15) -0.0400(11) -0.0237(13) 0.0125(10) C14 0.0660(14) 0.0706(14) 0.0852(16) -0.0407(12) -0.0257(13) -0.0016(12) C15 0.0622(13) 0.0694(14) 0.0702(13) -0.0305(11) -0.0357(11) 0.0131(11) C16 0.0556(11) 0.0474(10) 0.0527(10) -0.0235(8) -0.0242(9) 0.0158(8) 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 for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.1023 0.0942 ; International Tables for Crystallography (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 _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 P1 C1 117.54(9) yes . . . O1 P1 C4 117.15(9) yes . . . O1 P1 C5 114.85(9) yes . . . C1 P1 C4 91.38(8) yes . . . C1 P1 C5 107.43(9) yes . . . C4 P1 C5 105.60(9) yes . . . C6 N1 C7 117.19(16) yes . . . C9 N2 C10 117.45(16) yes . . . P1 C1 C2 110.94(12) yes . . . P1 C1 C6 130.46(12) yes . . . C2 C1 C6 118.59(16) yes . . . C1 C2 C3 113.41(15) yes . . . C1 C2 C8 118.97(14) yes . . . C3 C2 C8 127.59(13) yes . . . C2 C3 C4 113.17(12) yes . . . C2 C3 C11 127.72(16) yes . . . C4 C3 C11 119.10(15) yes . . . P1 C4 C3 111.08(11) yes . . . P1 C4 C9 130.18(13) yes . . . C3 C4 C9 118.74(13) yes . . . P1 C5 C12 122.80(16) yes . . . P1 C5 C16 118.35(15) yes . . . C12 C5 C16 118.8(2) yes . . . N1 C6 C1 122.83(14) yes . . . N1 C7 C8 125.14(19) yes . . . C2 C8 C7 117.28(14) yes . . . N2 C9 C4 122.54(17) yes . . . N2 C10 C11 124.44(14) yes . . . C3 C11 C10 117.71(17) yes . . . C5 C12 C13 120.0(2) yes . . . C12 C13 C14 120.5(2) yes . . . C13 C14 C15 120.2(3) yes . . . C14 C15 C16 119.9(2) yes . . . C5 C16 C15 120.6(2) yes . . . N1 C6 H6 118.584 no . . . C1 C6 H6 118.584 no . . . N1 C7 H7 117.428 no . . . C8 C7 H7 117.430 no . . . C2 C8 H8 121.366 no . . . C7 C8 H8 121.359 no . . . N2 C9 H9 118.731 no . . . C4 C9 H9 118.729 no . . . N2 C10 H10 117.774 no . . . C11 C10 H10 117.785 no . . . C3 C11 H11 121.141 no . . . C10 C11 H11 121.146 no . . . C5 C12 H12 120.013 no . . . C13 C12 H12 119.997 no . . . C12 C13 H13 119.774 no . . . C14 C13 H13 119.773 no . . . C13 C14 H14 119.895 no . . . C15 C14 H14 119.898 no . . . C14 C15 H15 120.028 no . . . C16 C15 H15 120.038 no . . . C5 C16 H16 119.713 no . . . C15 C16 H16 119.717 no . . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 P1 O1 1.4801(15) yes . . P1 C1 1.811(2) yes . . P1 C4 1.8096(16) yes . . P1 C5 1.797(2) yes . . N1 C6 1.337(3) yes . . N1 C7 1.333(2) yes . . N2 C9 1.342(2) yes . . N2 C10 1.341(3) yes . . C1 C2 1.403(2) yes . . C1 C6 1.391(2) yes . . C2 C3 1.481(2) yes . . C2 C8 1.387(3) yes . . C3 C4 1.405(3) yes . . C3 C11 1.380(2) yes . . C4 C9 1.393(2) yes . . C5 C12 1.389(3) yes . . C5 C16 1.397(3) yes . . C7 C8 1.383(3) yes . . C10 C11 1.390(3) yes . . C12 C13 1.387(4) yes . . C13 C14 1.371(4) yes . . C14 C15 1.378(4) yes . . C15 C16 1.377(4) yes . . C6 H6 0.930 no . . C7 H7 0.930 no . . C8 H8 0.930 no . . C9 H9 0.930 no . . C10 H10 0.930 no . . C11 H11 0.930 no . . C12 H12 0.930 no . . C13 H13 0.930 no . . C14 H14 0.930 no . . C15 H15 0.930 no . . C16 H16 0.930 no . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 C6 3.581(3) no . . O1 C9 3.567(2) no . . O1 C16 3.428(3) no . . N1 C2 2.790(3) no . . N2 C3 2.792(3) no . . C1 C7 2.701(3) no . . C1 C12 3.190(3) no . . C4 C10 2.710(2) no . . C4 C16 3.325(3) no . . C5 C14 2.776(4) no . . C6 C8 2.741(3) no . . C6 C12 3.543(4) no . . C8 C11 3.171(3) no . . C9 C11 2.746(3) no . . C9 C16 3.564(4) no . . C12 C15 2.767(4) no . . C13 C16 2.755(4) no . . O1 C9 3.323(3) no . 2_676 O1 C14 3.431(3) no . 1_655 O1 C15 3.407(3) no . 1_655 O1 C16 3.450(3) no . 2_676 N1 N1 3.576(3) no . 2_667 N1 C6 3.599(3) no . 2_667 N1 C10 3.410(3) no . 1_645 N1 C10 3.488(4) no . 2_677 N1 C11 3.532(3) no . 2_677 N2 C13 3.587(4) no . 1_565 C2 C2 3.541(3) no . 2_677 C3 C8 3.581(4) no . 2_677 C4 C7 3.558(4) no . 2_677 C6 N1 3.599(3) no . 2_667 C6 C11 3.536(4) no . 2_677 C7 C4 3.558(4) no . 2_677 C7 C15 3.566(4) no . 1_556 C8 C3 3.581(4) no . 2_677 C9 O1 3.323(3) no . 2_676 C10 N1 3.410(3) no . 1_465 C10 N1 3.488(4) no . 2_677 C11 N1 3.532(3) no . 2_677 C11 C6 3.536(4) no . 2_677 C11 C12 3.536(3) no . 2_577 C12 C11 3.536(3) no . 2_577 C13 N2 3.587(4) no . 1_545 C14 O1 3.431(3) no . 1_455 C15 O1 3.407(3) no . 1_455 C15 C7 3.566(4) no . 1_554 C16 O1 3.450(3) no . 2_676 P1 H6 3.0634 no . . P1 H9 3.0604 no . . P1 H12 2.9146 no . . P1 H16 2.8200 no . . O1 H6 3.4643 no . . O1 H9 3.4435 no . . O1 H16 3.2745 no . . N1 H8 3.2389 no . . N2 H11 3.2446 no . . C1 H8 3.2549 no . . C1 H12 2.7847 no . . C2 H6 3.2382 no . . C2 H7 3.1979 no . . C2 H11 2.7924 no . . C3 H8 2.8004 no . . C3 H9 3.2429 no . . C3 H10 3.2027 no . . C4 H11 3.2506 no . . C4 H16 3.1170 no . . C5 H13 3.2411 no . . C5 H15 3.2480 no . . C6 H7 3.1125 no . . C6 H12 2.8259 no . . C7 H6 3.1188 no . . C8 H11 2.9639 no . . C9 H10 3.1275 no . . C9 H16 3.0466 no . . C10 H9 3.1330 no . . C11 H8 2.9695 no . . C12 H6 3.4136 no . . C12 H14 3.2316 no . . C12 H16 3.2380 no . . C13 H15 3.2216 no . . C14 H12 3.2300 no . . C14 H16 3.2234 no . . C15 H13 3.2211 no . . C16 H9 3.2559 no . . C16 H12 3.2410 no . . C16 H14 3.2244 no . . H6 H12 2.6723 no . . H7 H8 2.2960 no . . H8 H11 2.5027 no . . H9 H16 2.5500 no . . H10 H11 2.3045 no . . H12 H13 2.3133 no . . H13 H14 2.2962 no . . H14 H15 2.3074 no . . H15 H16 2.3039 no . . P1 H9 3.5658 no . 2_676 O1 H8 3.0795 no . 2_677 O1 H9 2.3983 no . 2_676 O1 H14 3.1812 no . 1_655 O1 H15 3.1384 no . 1_655 O1 H16 2.5348 no . 2_676 N1 H6 3.5213 no . 2_667 N1 H10 2.5533 no . 1_645 N1 H12 2.8250 no . 2_667 N1 H13 3.4983 no . 2_667 N2 H6 2.9988 no . 1_465 N2 H13 2.7280 no . 1_565 N2 H15 3.3186 no . 2_576 C4 H7 3.5618 no . 2_677 C5 H11 3.1088 no . 2_577 C6 H10 3.0926 no . 1_645 C6 H11 3.4889 no . 2_677 C7 H12 3.0905 no . 2_667 C7 H13 3.4617 no . 2_667 C7 H15 3.2662 no . 1_556 C8 H15 3.2715 no . 1_556 C9 H7 3.4034 no . 2_677 C9 H13 3.0821 no . 1_565 C9 H15 3.0626 no . 2_576 C10 H6 3.2883 no . 1_465 C10 H10 3.5007 no . 2_587 C10 H12 3.4037 no . 2_577 C12 H7 3.2700 no . 2_667 C12 H10 3.0938 no . 2_577 C12 H11 2.9016 no . 2_577 C13 H7 3.3514 no . 2_667 C13 H10 3.4105 no . 2_577 C13 H11 3.1080 no . 2_577 C14 H7 3.5525 no . 1_554 C14 H11 3.4827 no . 2_577 C14 H14 3.3419 no . 2_566 C15 H7 2.8328 no . 1_554 C15 H8 3.4186 no . 1_554 C15 H9 3.4078 no . 2_576 C15 H16 3.4573 no . 2_576 C16 H7 3.0569 no . 1_554 C16 H11 3.5004 no . 2_577 C16 H15 3.3509 no . 2_576 H6 N1 3.5213 no . 2_667 H6 N2 2.9988 no . 1_645 H6 C10 3.2883 no . 1_645 H6 H10 2.8259 no . 1_645 H6 H11 3.5746 no . 2_677 H7 C4 3.5618 no . 2_677 H7 C9 3.4034 no . 2_677 H7 C12 3.2700 no . 2_667 H7 C13 3.3514 no . 2_667 H7 C14 3.5525 no . 1_556 H7 C15 2.8328 no . 1_556 H7 C16 3.0569 no . 1_556 H7 H9 3.5895 no . 2_677 H7 H12 2.6707 no . 2_667 H7 H13 2.8318 no . 2_667 H7 H15 2.7318 no . 1_556 H7 H16 3.0948 no . 1_556 H8 O1 3.0795 no . 2_677 H8 C15 3.4186 no . 1_556 H8 H15 2.7907 no . 1_556 H8 H16 3.2055 no . 1_556 H9 P1 3.5658 no . 2_676 H9 O1 2.3983 no . 2_676 H9 C15 3.4078 no . 2_576 H9 H7 3.5895 no . 2_677 H9 H13 2.9742 no . 1_565 H9 H14 3.2559 no . 2_576 H9 H15 2.6610 no . 2_576 H9 H16 3.5520 no . 2_676 H10 N1 2.5533 no . 1_465 H10 C6 3.0926 no . 1_465 H10 C10 3.5007 no . 2_587 H10 C12 3.0938 no . 2_577 H10 C13 3.4105 no . 2_577 H10 H6 2.8259 no . 1_465 H10 H10 3.1416 no . 2_587 H10 H12 2.7281 no . 2_577 H10 H13 3.2956 no . 2_577 H11 C5 3.1088 no . 2_577 H11 C6 3.4889 no . 2_677 H11 C12 2.9016 no . 2_577 H11 C13 3.1080 no . 2_577 H11 C14 3.4827 no . 2_577 H11 C16 3.5004 no . 2_577 H11 H6 3.5746 no . 2_677 H11 H12 3.1937 no . 2_577 H11 H13 3.5010 no . 2_577 H12 N1 2.8250 no . 2_667 H12 C7 3.0905 no . 2_667 H12 C10 3.4037 no . 2_577 H12 H7 2.6707 no . 2_667 H12 H10 2.7281 no . 2_577 H12 H11 3.1937 no . 2_577 H13 N1 3.4983 no . 2_667 H13 N2 2.7280 no . 1_545 H13 C7 3.4617 no . 2_667 H13 C9 3.0821 no . 1_545 H13 H7 2.8318 no . 2_667 H13 H9 2.9742 no . 1_545 H13 H10 3.2956 no . 2_577 H13 H11 3.5010 no . 2_577 H13 H14 3.5910 no . 2_566 H14 O1 3.1812 no . 1_455 H14 C14 3.3419 no . 2_566 H14 H9 3.2559 no . 2_576 H14 H13 3.5910 no . 2_566 H14 H14 2.4612 no . 2_566 H15 O1 3.1384 no . 1_455 H15 N2 3.3186 no . 2_576 H15 C7 3.2662 no . 1_554 H15 C8 3.2715 no . 1_554 H15 C9 3.0626 no . 2_576 H15 C16 3.3509 no . 2_576 H15 H7 2.7318 no . 1_554 H15 H8 2.7907 no . 1_554 H15 H9 2.6610 no . 2_576 H15 H15 3.3840 no . 2_576 H15 H16 2.8039 no . 2_576 H16 O1 2.5348 no . 2_676 H16 C15 3.4573 no . 2_576 H16 H7 3.0948 no . 1_554 H16 H8 3.2055 no . 1_554 H16 H9 3.5520 no . 2_676 H16 H15 2.8039 no . 2_576 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O1 P1 C1 C2 123.01(12) no . . . . O1 P1 C1 C6 -55.6(2) no . . . . O1 P1 C4 C3 -123.69(12) no . . . . O1 P1 C4 C9 55.3(2) no . . . . O1 P1 C5 C12 110.62(11) no . . . . O1 P1 C5 C16 -71.15(11) no . . . . C1 P1 C4 C3 -1.54(13) no . . . . C1 P1 C4 C9 177.50(18) no . . . . C4 P1 C1 C2 1.18(14) no . . . . C4 P1 C1 C6 -177.47(18) no . . . . C1 P1 C5 C12 -22.19(11) no . . . . C1 P1 C5 C16 156.04(8) no . . . . C5 P1 C1 C2 -105.65(13) no . . . . C5 P1 C1 C6 75.70(19) no . . . . C4 P1 C5 C12 -118.73(11) no . . . . C4 P1 C5 C16 59.51(11) no . . . . C5 P1 C4 C3 106.99(13) no . . . . C5 P1 C4 C9 -73.97(18) no . . . . C6 N1 C7 C8 0.3(4) no . . . . C7 N1 C6 C1 -0.9(3) no . . . . C9 N2 C10 C11 0.5(3) no . . . . C10 N2 C9 C4 0.6(3) no . . . . P1 C1 C2 C3 -0.5(2) no . . . . P1 C1 C2 C8 -178.91(12) no . . . . P1 C1 C6 N1 179.33(15) no . . . . C2 C1 C6 N1 0.8(3) no . . . . C6 C1 C2 C3 178.28(17) no . . . . C6 C1 C2 C8 -0.1(3) no . . . . C1 C2 C3 C4 -0.6(2) no . . . . C1 C2 C3 C11 -179.37(17) no . . . . C1 C2 C8 C7 -0.4(3) no . . . . C3 C2 C8 C7 -178.54(18) no . . . . C8 C2 C3 C4 177.56(19) no . . . . C8 C2 C3 C11 -1.2(3) no . . . . C2 C3 C4 P1 1.5(2) no . . . . C2 C3 C4 C9 -177.65(16) no . . . . C2 C3 C11 C10 178.45(18) no . . . . C4 C3 C11 C10 -0.2(3) no . . . . C11 C3 C4 P1 -179.64(16) no . . . . C11 C3 C4 C9 1.2(3) no . . . . P1 C4 C9 N2 179.60(14) no . . . . C3 C4 C9 N2 -1.4(3) no . . . . P1 C5 C12 C13 177.08(9) no . . . . P1 C5 C16 C15 -176.66(9) no . . . . C12 C5 C16 C15 1.6(2) no . . . . C16 C5 C12 C13 -1.2(2) no . . . . N1 C7 C8 C2 0.4(4) no . . . . N2 C10 C11 C3 -0.7(3) no . . . . C5 C12 C13 C14 0.1(3) no . . . . C12 C13 C14 C15 0.5(3) no . . . . C13 C14 C15 C16 0.0(3) no . . . . C14 C15 C16 C5 -1.1(3) no . . . .