#------------------------------------------------------------------------------ #$Date: 2013-07-11 23:13:02 +0300 (Thu, 11 Jul 2013) $ #$Revision: 86737 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/54/2105474.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_2105474 loop_ _publ_author_name 'Tarahhomi, Atekeh' 'Pourayoubi, Mehrdad' 'Golen, James A.' 'Zargaran, Poorya' 'Elahi, Behrouz' 'Rheingold, Arnold L.' 'Leyva Ram\'irez, Marco A.' 'Mancilla Percino, Teresa' _publ_section_title ; Hirshfeld surface analysis of new phosphoramidates ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 260 _journal_page_last 270 _journal_paper_doi 10.1107/S2052519213009445 _journal_volume 69 _journal_year 2013 _chemical_formula_moiety 'C32 H40 N4 O3 P2' _chemical_formula_sum 'C32 H40 N4 O3 P2' _chemical_formula_weight 590.62 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.341(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 19.050(3) _cell_length_b 8.5308(12) _cell_length_c 18.821(3) _cell_measurement_reflns_used 3174 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 68.50 _cell_measurement_theta_min 32.88 _cell_volume 3033.6(8) _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); enCIFer (Allen et al., 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'doubly curved mirrors' _diffrn_radiation_source 'Cu rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12338 _diffrn_reflns_theta_full 68.22 _diffrn_reflns_theta_max 68.22 _diffrn_reflns_theta_min 5.69 _exptl_absorpt_coefficient_mu 1.617 _exptl_absorpt_correction_T_max 0.8550 _exptl_absorpt_correction_T_min 0.7380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1256 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.306 _refine_diff_density_min -0.330 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2662 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0332 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+3.5908P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.0850 _reflns_number_gt 2640 _reflns_number_total 2662 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL V in C2/c CELL 1.54178 19.0500 8.5308 18.8211 90.000 97.341 90.000 ZERR 4.00 0.0032 0.0012 0.0027 0.000 0.006 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O P UNIT 128 160 16 12 8 TEMP -173 CONF REM COLORLESS BLOC AT20 SIZE 0.10 0.10 0.20 L.S. 6 ACTA BOND $h FMAP 2 PLAN 10 WGHT 0.033700 3.590800 FVAR 0.19777 P1 5 0.011654 0.710271 0.176053 11.00000 0.01310 0.00983 = 0.01208 0.00041 0.00281 0.00006 O1 4 -0.046949 0.603779 0.150536 11.00000 0.01610 0.01338 = 0.01767 -0.00030 0.00211 -0.00121 O2 4 0.000000 0.796830 0.250000 10.50000 0.01607 0.01008 = 0.01467 0.00000 0.00440 0.00000 N1 3 0.087334 0.616424 0.187190 11.00000 0.01426 0.01177 = 0.01682 -0.00036 0.00327 -0.00020 N2 3 0.024393 0.864831 0.128109 11.00000 0.01968 0.01156 = 0.01389 0.00130 0.00427 0.00076 C1 1 0.089498 0.449473 0.206418 11.00000 0.01739 0.01326 = 0.01701 0.00185 0.00429 0.00256 AFIX 23 H1B 2 0.040450 0.409734 0.204320 11.00000 -1.20000 H1C 2 0.112539 0.437911 0.256349 11.00000 -1.20000 AFIX 0 C2 1 0.129042 0.350874 0.157629 11.00000 0.01178 0.01271 = 0.02076 -0.00174 0.00412 -0.00281 C3 1 0.117739 0.370837 0.083498 11.00000 0.01687 0.01488 = 0.02163 -0.00047 0.00368 -0.00302 AFIX 43 H3A 2 0.087737 0.452734 0.063409 11.00000 -1.20000 AFIX 0 C4 1 0.150013 0.271888 0.038798 11.00000 0.02328 0.02185 = 0.02139 -0.00542 0.00826 -0.00801 AFIX 43 H4A 2 0.142118 0.286584 -0.011625 11.00000 -1.20000 AFIX 0 C5 1 0.193732 0.151706 0.067627 11.00000 0.01944 0.02037 = 0.03262 -0.01227 0.01030 -0.00426 AFIX 43 H5A 2 0.215425 0.083481 0.037007 11.00000 -1.20000 AFIX 0 C6 1 0.205687 0.131429 0.141338 11.00000 0.01571 0.01708 = 0.03500 -0.00532 0.00102 0.00194 AFIX 43 H6A 2 0.235808 0.049546 0.161235 11.00000 -1.20000 AFIX 0 C7 1 0.173545 0.231089 0.186221 11.00000 0.01555 0.01642 = 0.02244 -0.00211 0.00067 -0.00041 AFIX 43 H7A 2 0.182084 0.217122 0.236663 11.00000 -1.20000 AFIX 0 C8 1 0.152710 0.700784 0.212656 11.00000 0.01467 0.02066 = 0.02853 -0.00363 0.00268 -0.00034 AFIX 137 H8A 2 0.193116 0.645865 0.196758 11.00000 -1.50000 H8B 2 0.158632 0.705491 0.265107 11.00000 -1.50000 H8C 2 0.150114 0.807428 0.193139 11.00000 -1.50000 AFIX 0 C9 1 0.009102 1.027824 0.145341 11.00000 0.01911 0.01102 = 0.01613 0.00154 0.00270 -0.00264 AFIX 23 H9A 2 0.040245 1.096807 0.120877 11.00000 -1.20000 H9B 2 0.021827 1.042981 0.197548 11.00000 -1.20000 AFIX 0 C10 1 -0.066884 1.081482 0.125180 11.00000 0.01884 0.01400 = 0.01061 -0.00159 0.00336 -0.00106 C11 1 -0.079941 1.239601 0.109476 11.00000 0.02235 0.01400 = 0.01646 -0.00080 0.00469 -0.00177 AFIX 43 H11A 2 -0.041279 1.310167 0.110184 11.00000 -1.20000 AFIX 0 C12 1 -0.148503 1.295223 0.092856 11.00000 0.02831 0.01593 = 0.01967 0.00214 0.00540 0.00564 AFIX 43 H12A 2 -0.156526 1.403152 0.082346 11.00000 -1.20000 AFIX 0 C13 1 -0.205294 1.193258 0.091593 11.00000 0.01915 0.02539 = 0.01906 -0.00107 0.00342 0.00527 AFIX 43 H13A 2 -0.252298 1.230718 0.079773 11.00000 -1.20000 AFIX 0 C14 1 -0.193016 1.035617 0.107754 11.00000 0.01842 0.02220 = 0.02157 -0.00163 0.00383 -0.00297 AFIX 43 H14A 2 -0.231826 0.965590 0.107466 11.00000 -1.20000 AFIX 0 C15 1 -0.124343 0.980179 0.124293 11.00000 0.02186 0.01363 = 0.01737 0.00013 0.00338 -0.00122 AFIX 43 H15A 2 -0.116481 0.872324 0.135088 11.00000 -1.20000 AFIX 0 C16 1 0.035944 0.835474 0.053762 11.00000 0.02643 0.01769 = 0.01570 0.00253 0.00607 0.00201 AFIX 137 H16A 2 0.074043 0.903354 0.041318 11.00000 -1.50000 H16B 2 -0.007657 0.857951 0.021823 11.00000 -1.50000 H16C 2 0.049168 0.725485 0.048429 11.00000 -1.50000 HKLF 4 REM V in C2/c REM R1 = 0.0332 for 2640 Fo > 4sig(Fo) and 0.0334 for all 2662 data REM 188 parameters refined using 0 restraints END WGHT 0.0329 3.6411 REM Highest difference peak 0.306, deepest hole -0.330, 1-sigma level 0.043 Q1 1 0.0541 0.6573 0.1777 11.00000 0.05 0.31 Q2 1 0.0361 0.8133 0.1596 11.00000 0.05 0.28 Q3 1 0.1109 0.4004 0.1800 11.00000 0.05 0.27 Q4 1 -0.0510 0.7042 0.1576 11.00000 0.05 0.25 Q5 1 0.0117 0.7993 0.1437 11.00000 0.05 0.25 Q6 1 -0.1176 1.2775 0.1244 11.00000 0.05 0.23 Q7 1 -0.0318 1.0599 0.1387 11.00000 0.05 0.22 Q8 1 0.0087 0.9411 0.1377 11.00000 0.05 0.22 Q9 1 -0.0201 0.6178 0.1819 11.00000 0.05 0.22 Q10 1 0.1620 0.3136 0.1734 11.00000 0.05 0.21 ; _[local]_cod_data_source_file so5063.cif _[local]_cod_data_source_block V _[local]_cod_cif_authors_sg_H-M C2/c _cod_database_code 2105474 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity P P1 0.011654(17) 0.71027(4) 0.176053(16) 0.01157(13) Uani d . 1 1 O O1 -0.04695(5) 0.60378(11) 0.15054(5) 0.0157(2) Uani d . 1 1 O O2 0.0000 0.79683(14) 0.2500 0.0134(3) Uani d S 1 2 N N1 0.08733(6) 0.61642(13) 0.18719(6) 0.0142(3) Uani d . 1 1 N N2 0.02439(6) 0.86483(13) 0.12811(6) 0.0149(3) Uani d . 1 1 C C1 0.08950(7) 0.44947(15) 0.20642(7) 0.0157(3) Uani d . 1 1 H H1B 0.0404 0.4097 0.2043 0.019 Uiso calc R 1 1 H H1C 0.1125 0.4379 0.2563 0.019 Uiso calc R 1 1 C C2 0.12904(7) 0.35087(15) 0.15763(7) 0.0149(3) Uani d . 1 1 C C3 0.11774(7) 0.37084(16) 0.08350(7) 0.0177(3) Uani d . 1 1 H H3A 0.0877 0.4527 0.0634 0.021 Uiso calc R 1 1 C C4 0.15001(8) 0.27189(17) 0.03880(8) 0.0217(3) Uani d . 1 1 H H4A 0.1421 0.2866 -0.0116 0.026 Uiso calc R 1 1 C C5 0.19373(8) 0.15171(17) 0.06763(8) 0.0235(3) Uani d . 1 1 H H5A 0.2154 0.0835 0.0370 0.028 Uiso calc R 1 1 C C6 0.20569(8) 0.13143(17) 0.14134(8) 0.0228(3) Uani d . 1 1 H H6A 0.2358 0.0495 0.1612 0.027 Uiso calc R 1 1 C C7 0.17354(7) 0.23109(16) 0.18622(8) 0.0183(3) Uani d . 1 1 H H7A 0.1821 0.2171 0.2367 0.022 Uiso calc R 1 1 C C8 0.15271(7) 0.70078(17) 0.21266(8) 0.0213(3) Uani d . 1 1 H H8A 0.1931 0.6459 0.1968 0.032 Uiso calc R 1 1 H H8B 0.1586 0.7055 0.2651 0.032 Uiso calc R 1 1 H H8C 0.1501 0.8074 0.1931 0.032 Uiso calc R 1 1 C C9 0.00910(7) 1.02782(15) 0.14534(7) 0.0154(3) Uani d . 1 1 H H9A 0.0402 1.0968 0.1209 0.018 Uiso calc R 1 1 H H9B 0.0218 1.0430 0.1975 0.018 Uiso calc R 1 1 C C10 -0.06688(7) 1.08148(16) 0.12518(6) 0.0144(3) Uani d . 1 1 C C11 -0.07994(8) 1.23960(16) 0.10948(7) 0.0174(3) Uani d . 1 1 H H11A -0.0413 1.3102 0.1102 0.021 Uiso calc R 1 1 C C12 -0.14850(8) 1.29522(17) 0.09286(8) 0.0211(3) Uani d . 1 1 H H12A -0.1565 1.4032 0.0823 0.025 Uiso calc R 1 1 C C13 -0.20529(8) 1.19326(18) 0.09159(8) 0.0211(3) Uani d . 1 1 H H13A -0.2523 1.2307 0.0798 0.025 Uiso calc R 1 1 C C14 -0.19302(8) 1.03562(17) 0.10775(7) 0.0206(3) Uani d . 1 1 H H14A -0.2318 0.9656 0.1075 0.025 Uiso calc R 1 1 C C15 -0.12434(7) 0.98018(16) 0.12429(7) 0.0175(3) Uani d . 1 1 H H15A -0.1165 0.8723 0.1351 0.021 Uiso calc R 1 1 C C16 0.03594(8) 0.83547(17) 0.05376(7) 0.0196(3) Uani d . 1 1 H H16A 0.0740 0.9034 0.0413 0.029 Uiso calc R 1 1 H H16B -0.0077 0.8580 0.0218 0.029 Uiso calc R 1 1 H H16C 0.0492 0.7255 0.0484 0.029 Uiso calc R 1 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 0.0131(2) 0.00983(19) 0.01208(19) 0.00006(12) 0.00281(13) 0.00041(11) O1 0.0161(5) 0.0134(5) 0.0177(5) -0.0012(4) 0.0021(4) -0.0003(4) O2 0.0161(7) 0.0101(6) 0.0147(6) 0.000 0.0044(5) 0.000 N1 0.0143(6) 0.0118(5) 0.0168(5) -0.0002(4) 0.0033(4) -0.0004(4) N2 0.0197(6) 0.0116(6) 0.0139(5) 0.0008(4) 0.0043(4) 0.0013(4) C1 0.0174(7) 0.0133(7) 0.0170(6) 0.0026(5) 0.0043(5) 0.0018(5) C2 0.0118(6) 0.0127(6) 0.0208(7) -0.0028(5) 0.0041(5) -0.0017(5) C3 0.0169(7) 0.0149(7) 0.0216(7) -0.0030(5) 0.0037(5) -0.0005(5) C4 0.0233(8) 0.0218(7) 0.0214(7) -0.0080(6) 0.0083(6) -0.0054(6) C5 0.0194(8) 0.0204(7) 0.0326(8) -0.0043(6) 0.0103(6) -0.0123(6) C6 0.0157(7) 0.0171(7) 0.0350(8) 0.0019(5) 0.0010(6) -0.0053(6) C7 0.0156(7) 0.0164(7) 0.0224(7) -0.0004(5) 0.0007(5) -0.0021(5) C8 0.0147(7) 0.0207(7) 0.0285(8) -0.0003(5) 0.0027(6) -0.0036(6) C9 0.0191(7) 0.0110(6) 0.0161(6) -0.0026(5) 0.0027(5) 0.0015(5) C10 0.0188(7) 0.0140(6) 0.0106(6) -0.0011(5) 0.0034(5) -0.0016(5) C11 0.0224(7) 0.0140(6) 0.0165(6) -0.0018(6) 0.0047(5) -0.0008(5) C12 0.0283(8) 0.0159(7) 0.0197(7) 0.0056(6) 0.0054(6) 0.0021(5) C13 0.0191(7) 0.0254(8) 0.0191(7) 0.0053(6) 0.0034(5) -0.0011(6) C14 0.0184(7) 0.0222(7) 0.0216(7) -0.0030(6) 0.0038(5) -0.0016(6) C15 0.0219(7) 0.0136(7) 0.0174(6) -0.0012(5) 0.0034(5) 0.0001(5) C16 0.0264(8) 0.0177(7) 0.0157(7) 0.0020(6) 0.0061(5) 0.0025(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle O1 P1 O2 . 112.41(5) O1 P1 N2 . 118.57(6) O2 P1 N2 . 98.83(6) O1 P1 N1 . 111.01(6) O2 P1 N1 . 109.18(4) N2 P1 N1 . 105.94(6) P1 O2 P1 2 125.61(8) C8 N1 C1 . 113.57(11) C8 N1 P1 . 119.94(9) C1 N1 P1 . 120.11(9) C9 N2 C16 . 115.58(10) C9 N2 P1 . 126.58(9) C16 N2 P1 . 116.14(9) N1 C1 C2 . 112.92(11) N1 C1 H1B . 109.0 C2 C1 H1B . 109.0 N1 C1 H1C . 109.0 C2 C1 H1C . 109.0 H1B C1 H1C . 107.8 C7 C2 C3 . 119.02(13) C7 C2 C1 . 119.93(12) C3 C2 C1 . 120.89(12) C4 C3 C2 . 120.52(13) C4 C3 H3A . 119.7 C2 C3 H3A . 119.7 C5 C4 C3 . 120.15(14) C5 C4 H4A . 119.9 C3 C4 H4A . 119.9 C4 C5 C6 . 119.79(13) C4 C5 H5A . 120.1 C6 C5 H5A . 120.1 C5 C6 C7 . 120.07(14) C5 C6 H6A . 120.0 C7 C6 H6A . 120.0 C2 C7 C6 . 120.44(14) C2 C7 H7A . 119.8 C6 C7 H7A . 119.8 N1 C8 H8A . 109.5 N1 C8 H8B . 109.5 H8A C8 H8B . 109.5 N1 C8 H8C . 109.5 H8A C8 H8C . 109.5 H8B C8 H8C . 109.5 N2 C9 C10 . 116.14(11) N2 C9 H9A . 108.3 C10 C9 H9A . 108.3 N2 C9 H9B . 108.3 C10 C9 H9B . 108.3 H9A C9 H9B . 107.4 C15 C10 C11 . 118.57(13) C15 C10 C9 . 122.56(12) C11 C10 C9 . 118.83(12) C12 C11 C10 . 121.01(13) C12 C11 H11A . 119.5 C10 C11 H11A . 119.5 C13 C12 C11 . 119.97(13) C13 C12 H12A . 120.0 C11 C12 H12A . 120.0 C12 C13 C14 . 119.58(14) C12 C13 H13A . 120.2 C14 C13 H13A . 120.2 C15 C14 C13 . 120.35(14) C15 C14 H14A . 119.8 C13 C14 H14A . 119.8 C14 C15 C10 . 120.51(13) C14 C15 H15A . 119.7 C10 C15 H15A . 119.7 N2 C16 H16A . 109.5 N2 C16 H16B . 109.5 H16A C16 H16B . 109.5 N2 C16 H16C . 109.5 H16A C16 H16C . 109.5 H16B C16 H16C . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance P1 O1 . 1.4715(10) P1 O2 . 1.6157(6) P1 N2 . 1.6333(11) P1 N1 . 1.6389(11) O2 P1 2 1.6158(6) N1 C8 . 1.4650(17) N1 C1 . 1.4688(17) N2 C9 . 1.4655(17) N2 C16 . 1.4656(17) C1 C2 . 1.5149(18) C1 H1B . 0.9900 C1 H1C . 0.9900 C2 C7 . 1.3914(19) C2 C3 . 1.3947(19) C3 C4 . 1.389(2) C3 H3A . 0.9500 C4 C5 . 1.387(2) C4 H4A . 0.9500 C5 C6 . 1.388(2) C5 H5A . 0.9500 C6 C7 . 1.394(2) C6 H6A . 0.9500 C7 H7A . 0.9500 C8 H8A . 0.9800 C8 H8B . 0.9800 C8 H8C . 0.9800 C9 C10 . 1.5194(19) C9 H9A . 0.9900 C9 H9B . 0.9900 C10 C15 . 1.3931(19) C10 C11 . 1.3964(19) C11 C12 . 1.387(2) C11 H11A . 0.9500 C12 C13 . 1.386(2) C12 H12A . 0.9500 C13 C14 . 1.392(2) C13 H13A . 0.9500 C14 C15 . 1.388(2) C14 H14A . 0.9500 C15 H15A . 0.9500 C16 H16A . 0.9800 C16 H16B . 0.9800 C16 H16C . 0.9800 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion O1 P1 O2 P1 2 57.39(4) N2 P1 O2 P1 2 -176.63(4) N1 P1 O2 P1 2 -66.25(5) O1 P1 N1 C8 . -179.80(9) O2 P1 N1 C8 . -55.33(11) N2 P1 N1 C8 . 50.24(11) O1 P1 N1 C1 . -29.65(11) O2 P1 N1 C1 . 94.82(10) N2 P1 N1 C1 . -159.61(9) O1 P1 N2 C9 . 107.25(11) O2 P1 N2 C9 . -14.35(11) N1 P1 N2 C9 . -127.31(11) O1 P1 N2 C16 . -57.16(12) O2 P1 N2 C16 . -178.75(9) N1 P1 N2 C16 . 68.29(11) C8 N1 C1 C2 . -79.60(14) P1 N1 C1 C2 . 128.47(10) N1 C1 C2 C7 . 139.80(12) N1 C1 C2 C3 . -44.81(17) C7 C2 C3 C4 . 0.5(2) C1 C2 C3 C4 . -174.97(12) C2 C3 C4 C5 . 0.2(2) C3 C4 C5 C6 . -0.6(2) C4 C5 C6 C7 . 0.3(2) C3 C2 C7 C6 . -0.7(2) C1 C2 C7 C6 . 174.75(12) C5 C6 C7 C2 . 0.3(2) C16 N2 C9 C10 . 81.28(14) P1 N2 C9 C10 . -83.20(14) N2 C9 C10 C15 . 30.75(17) N2 C9 C10 C11 . -151.68(12) C15 C10 C11 C12 . -0.41(19) C9 C10 C11 C12 . -178.07(12) C10 C11 C12 C13 . -0.1(2) C11 C12 C13 C14 . 0.6(2) C12 C13 C14 C15 . -0.7(2) C13 C14 C15 C10 . 0.2(2) C11 C10 C15 C14 . 0.33(19) C9 C10 C15 C14 . 177.91(12)