#------------------------------------------------------------------------------ #$Date: 2014-01-12 10:14:05 +0000 (Sun, 12 Jan 2014) $ #$Revision: 92280 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238899.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_2238899 loop_ _publ_author_name 'Chyba, Jan' 'Necas, Marek' 'Pinkas, Jiri' _publ_section_title ; Diethyl [4-(2,2':6',2''-terpyridine-4'-yl)phenyl]phosphonate ; _journal_coeditor_code NC2320 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1824 _journal_paper_doi 10.1107/S1600536813031541 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C25 H24 N3 O3 P' _chemical_formula_moiety 'C25 H24 N3 O3 P' _chemical_formula_sum 'C25 H24 N3 O3 P' _chemical_formula_weight 445.44 _chemical_name_systematic ; Diethyl [4-(2,2':6',2''-terpyridine-4'-yl)phenyl]phosphonate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 111.674(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.5290(4) _cell_length_b 13.0264(4) _cell_length_c 14.5681(5) _cell_measurement_reflns_used 25622 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.10 _cell_measurement_theta_min 2.87 _cell_volume 2209.53(13) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 8.4353 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur (Sapphire2)' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23115 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.87 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.259 _refine_diff_density_min -0.356 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 3886 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0298 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.0747 _reflns_number_gt 2809 _reflns_number_total 3886 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL chyba1 in P2(1)/c CELL 0.71073 12.5290 13.0264 14.5681 90.000 111.674 90.000 ZERR 4.00 0.0004 0.0004 0.0005 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O P UNIT 100 96 12 12 4 L.S. 12 BOND $H FMAP 2 PLAN 10 OMIT 0 50 TEMP -153 SIZE 0.40 0.40 0.30 ACTA WGHT 0.042800 FVAR 0.14822 P1 5 0.501199 0.720763 -0.001999 11.00000 0.02052 0.01997 = 0.02000 0.00025 0.00562 -0.00170 O1 4 0.465304 0.836497 -0.024921 11.00000 0.02673 0.02113 = 0.02639 0.00435 0.00022 -0.00127 O2 4 0.393641 0.676114 0.016870 11.00000 0.02025 0.02028 = 0.02638 0.00151 0.00689 -0.00035 O3 4 0.531638 0.665160 -0.076622 11.00000 0.02780 0.03157 = 0.02164 -0.00323 0.00858 -0.00475 C11 1 0.891356 0.759054 0.399198 11.00000 0.01921 0.02232 = 0.02021 0.00248 0.00933 -0.00053 C12 1 0.980931 0.688364 0.435987 11.00000 0.02118 0.02237 = 0.01891 -0.00257 0.00723 -0.00136 AFIX 43 H12A 2 0.983925 0.630027 0.397879 11.00000 -1.20000 AFIX 0 C13 1 1.066114 0.703912 0.529143 11.00000 0.02009 0.02216 = 0.02016 0.00194 0.00792 -0.00311 N14 3 1.065037 0.785755 0.585915 11.00000 0.02177 0.02412 = 0.01894 0.00165 0.00720 -0.00202 C15 1 0.978640 0.854417 0.549828 11.00000 0.01645 0.02244 = 0.01843 0.00340 0.00687 -0.00251 C16 1 0.891948 0.843093 0.457794 11.00000 0.01628 0.02076 = 0.01820 0.00322 0.00622 0.00126 AFIX 43 H16A 2 0.832772 0.893085 0.434821 11.00000 -1.20000 AFIX 0 C21 1 1.161562 0.628843 0.572978 11.00000 0.01918 0.02481 = 0.01974 0.00218 0.00711 -0.00302 N22 3 1.158255 0.542732 0.520776 11.00000 0.02525 0.02605 = 0.02685 0.00245 0.00866 0.00174 C23 1 1.241314 0.473143 0.561952 11.00000 0.02929 0.02481 = 0.03486 0.00293 0.01391 0.00120 AFIX 43 H23A 2 1.239786 0.411712 0.526343 11.00000 -1.20000 AFIX 0 C24 1 1.329015 0.485317 0.653028 11.00000 0.02033 0.02925 = 0.03497 0.01241 0.00704 0.00283 AFIX 43 H24A 2 1.385464 0.433455 0.679111 11.00000 -1.20000 AFIX 0 C25 1 1.332468 0.574688 0.705066 11.00000 0.02108 0.03684 = 0.02711 0.00604 0.00210 -0.00326 AFIX 43 H25A 2 1.391872 0.585895 0.767501 11.00000 -1.20000 AFIX 0 C26 1 1.248034 0.647320 0.664646 11.00000 0.02265 0.02618 = 0.02356 0.00005 0.00480 -0.00252 AFIX 43 H26A 2 1.248733 0.709486 0.698960 11.00000 -1.20000 AFIX 0 C31 1 0.978140 0.943057 0.614612 11.00000 0.01655 0.02282 = 0.01942 0.00283 0.00731 -0.00279 N32 3 0.891267 1.010707 0.577195 11.00000 0.02153 0.02845 = 0.02463 -0.00423 0.00574 -0.00091 C33 1 0.886295 1.089499 0.634768 11.00000 0.02188 0.03102 = 0.03230 -0.00686 0.00928 -0.00053 AFIX 43 H33A 2 0.826082 1.138100 0.608712 11.00000 -1.20000 AFIX 0 C34 1 0.964537 1.103801 0.730487 11.00000 0.02915 0.03220 = 0.02633 -0.01061 0.01410 -0.00742 AFIX 43 H34A 2 0.957687 1.160209 0.769280 11.00000 -1.20000 AFIX 0 C35 1 1.052275 1.033714 0.767361 11.00000 0.03077 0.03795 = 0.01950 -0.00415 0.00379 -0.00402 AFIX 43 H35A 2 1.107258 1.041042 0.832559 11.00000 -1.20000 AFIX 0 C36 1 1.059856 0.952692 0.708980 11.00000 0.02428 0.02755 = 0.01910 0.00130 0.00283 0.00099 AFIX 43 H36A 2 1.120425 0.904159 0.733300 11.00000 -1.20000 AFIX 0 C41 1 0.796110 0.746234 0.301295 11.00000 0.01991 0.01715 = 0.01977 0.00105 0.00536 -0.00099 C42 1 0.814949 0.703418 0.220643 11.00000 0.01674 0.02726 = 0.02608 -0.00259 0.00663 0.00345 AFIX 43 H42A 2 0.889542 0.679793 0.228460 11.00000 -1.20000 AFIX 0 C43 1 0.726224 0.694899 0.129230 11.00000 0.02456 0.02572 = 0.02149 -0.00438 0.00978 -0.00009 AFIX 43 H43A 2 0.740799 0.665693 0.075252 11.00000 -1.20000 AFIX 0 C44 1 0.615946 0.728807 0.115922 11.00000 0.01966 0.01516 = 0.02165 0.00204 0.00721 -0.00070 C45 1 0.596410 0.769877 0.197539 11.00000 0.01646 0.01918 = 0.02312 0.00221 0.00632 0.00221 AFIX 43 H45A 2 0.521457 0.792071 0.190167 11.00000 -1.20000 AFIX 0 C46 1 0.685154 0.778386 0.288630 11.00000 0.02273 0.01565 = 0.02047 -0.00091 0.00926 0.00158 AFIX 43 H46A 2 0.670422 0.806356 0.343013 11.00000 -1.20000 AFIX 0 C51 1 0.362293 0.866364 -0.107524 11.00000 0.02625 0.03000 = 0.02922 0.00622 0.00108 0.00140 AFIX 23 H51A 2 0.293017 0.850567 -0.092744 11.00000 -1.20000 H51B 2 0.357403 0.828416 -0.167827 11.00000 -1.20000 AFIX 0 C52 1 0.369909 0.979848 -0.122866 11.00000 0.02602 0.02687 = 0.02747 0.00337 0.00702 0.00287 AFIX 137 H52A 2 0.302736 1.002032 -0.179552 11.00000 -1.50000 H52B 2 0.439943 0.994775 -0.135465 11.00000 -1.50000 H52C 2 0.372011 1.016711 -0.063581 11.00000 -1.50000 AFIX 0 C61 1 0.399032 0.569724 0.050768 11.00000 0.02392 0.01802 = 0.02945 0.00166 0.00866 -0.00057 AFIX 23 H61A 2 0.479380 0.544911 0.074836 11.00000 -1.20000 H61B 2 0.352237 0.525063 -0.004402 11.00000 -1.20000 AFIX 0 C62 1 0.353567 0.566127 0.132832 11.00000 0.03507 0.03124 = 0.02872 0.00245 0.01149 -0.00436 AFIX 137 H62A 2 0.356178 0.495325 0.156309 11.00000 -1.50000 H62B 2 0.274035 0.590739 0.108343 11.00000 -1.50000 H62C 2 0.400843 0.609971 0.187354 11.00000 -1.50000 HKLF 4 REM chyba1 in P2(1)/c REM R1 = 0.0298 for 2809 Fo > 4sig(Fo) and 0.0492 for all 3886 data REM 291 parameters refined using 0 restraints END WGHT 0.0421 0.0000 REM Highest difference peak 0.259, deepest hole -0.356, 1-sigma level 0.037 Q1 1 0.5597 0.7143 0.0666 11.00000 0.05 0.26 Q2 1 0.8485 0.7543 0.3463 11.00000 0.05 0.22 Q3 1 1.2121 0.6480 0.6093 11.00000 0.05 0.20 Q4 1 0.8455 1.0136 0.4985 11.00000 0.05 0.19 Q5 1 0.8202 0.7580 0.2601 11.00000 0.05 0.19 Q6 1 1.1354 0.7990 0.6554 11.00000 0.05 0.18 Q7 1 0.6546 0.7064 0.1204 11.00000 0.05 0.18 Q8 1 1.0168 0.6814 0.4976 11.00000 0.05 0.17 Q9 1 0.6031 0.7284 0.1481 11.00000 0.05 0.17 Q10 1 1.3041 0.6158 0.6634 11.00000 0.05 0.17 ; _[local]_cod_data_source_file nc2320.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 2209.53(12) _cod_database_code 2238899 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.50120(4) 0.72076(3) -0.00200(3) 0.02069(12) Uani d . 1 1 O O1 0.46530(9) 0.83650(7) -0.02492(7) 0.0275(3) Uani d . 1 1 O O2 0.39364(8) 0.67611(7) 0.01687(7) 0.0228(3) Uani d . 1 1 O O3 0.53164(9) 0.66516(8) -0.07662(7) 0.0272(3) Uani d . 1 1 C C11 0.89136(13) 0.75905(11) 0.39920(11) 0.0200(3) Uani d . 1 1 C C12 0.98093(13) 0.68836(11) 0.43599(11) 0.0209(4) Uani d . 1 1 H H12 0.9839 0.6300 0.3979 0.025 Uiso calc R 1 1 C C13 1.06611(13) 0.70391(11) 0.52914(11) 0.0207(4) Uani d . 1 1 N N14 1.06504(10) 0.78575(9) 0.58592(9) 0.0217(3) Uani d . 1 1 C C15 0.97864(13) 0.85442(11) 0.54983(11) 0.0190(3) Uani d . 1 1 C C16 0.89195(13) 0.84309(11) 0.45779(10) 0.0185(3) Uani d . 1 1 H H16 0.8328 0.8931 0.4348 0.022 Uiso calc R 1 1 C C21 1.16156(13) 0.62884(11) 0.57298(11) 0.0213(4) Uani d . 1 1 N N22 1.15825(11) 0.54273(10) 0.52078(9) 0.0263(3) Uani d . 1 1 C C23 1.24131(14) 0.47314(12) 0.56195(12) 0.0291(4) Uani d . 1 1 H H23 1.2398 0.4117 0.5263 0.035 Uiso calc R 1 1 C C24 1.32901(14) 0.48532(12) 0.65303(12) 0.0291(4) Uani d . 1 1 H H24 1.3855 0.4335 0.6791 0.035 Uiso calc R 1 1 C C25 1.33247(14) 0.57469(13) 0.70507(12) 0.0303(4) Uani d . 1 1 H H25 1.3919 0.5859 0.7675 0.036 Uiso calc R 1 1 C C26 1.24803(13) 0.64732(12) 0.66465(11) 0.0252(4) Uani d . 1 1 H H26 1.2487 0.7095 0.6990 0.030 Uiso calc R 1 1 C C31 0.97814(13) 0.94306(11) 0.61461(11) 0.0194(4) Uani d . 1 1 N N32 0.89127(10) 1.01071(10) 0.57719(9) 0.0257(3) Uani d . 1 1 C C33 0.88630(14) 1.08950(12) 0.63477(12) 0.0286(4) Uani d . 1 1 H H33 0.8261 1.1381 0.6087 0.034 Uiso calc R 1 1 C C34 0.96454(14) 1.10380(12) 0.73049(12) 0.0281(4) Uani d . 1 1 H H34 0.9577 1.1602 0.7693 0.034 Uiso calc R 1 1 C C35 1.05227(15) 1.03371(12) 0.76736(12) 0.0310(4) Uani d . 1 1 H H35 1.1073 1.0410 0.8326 0.037 Uiso calc R 1 1 C C36 1.05986(14) 0.95269(11) 0.70898(11) 0.0251(4) Uani d . 1 1 H H36 1.1204 0.9042 0.7333 0.030 Uiso calc R 1 1 C C41 0.79611(13) 0.74623(10) 0.30129(10) 0.0195(3) Uani d . 1 1 C C42 0.81495(13) 0.70342(11) 0.22064(11) 0.0237(4) Uani d . 1 1 H H42 0.8895 0.6798 0.2285 0.028 Uiso calc R 1 1 C C43 0.72622(13) 0.69490(11) 0.12923(11) 0.0236(4) Uani d . 1 1 H H43 0.7408 0.6657 0.0753 0.028 Uiso calc R 1 1 C C44 0.61595(13) 0.72881(10) 0.11592(11) 0.0189(3) Uani d . 1 1 C C45 0.59641(13) 0.76988(11) 0.19754(11) 0.0199(3) Uani d . 1 1 H H45 0.5215 0.7921 0.1902 0.024 Uiso calc R 1 1 C C46 0.68515(13) 0.77839(10) 0.28863(11) 0.0192(3) Uani d . 1 1 H H46 0.6704 0.8064 0.3430 0.023 Uiso calc R 1 1 C C51 0.36229(14) 0.86636(12) -0.10752(12) 0.0311(4) Uani d . 1 1 H H51A 0.2930 0.8506 -0.0927 0.037 Uiso calc R 1 1 H H51B 0.3574 0.8284 -0.1678 0.037 Uiso calc R 1 1 C C52 0.36991(14) 0.97985(11) -0.12287(12) 0.0276(4) Uani d . 1 1 H H52A 0.3027 1.0020 -0.1796 0.041 Uiso calc R 1 1 H H52B 0.4399 0.9948 -0.1355 0.041 Uiso calc R 1 1 H H52C 0.3720 1.0167 -0.0636 0.041 Uiso calc R 1 1 C C61 0.39903(14) 0.56972(11) 0.05077(12) 0.0241(4) Uani d . 1 1 H H61A 0.4794 0.5449 0.0748 0.029 Uiso calc R 1 1 H H61B 0.3522 0.5251 -0.0044 0.029 Uiso calc R 1 1 C C62 0.35357(15) 0.56613(12) 0.13283(11) 0.0318(4) Uani d . 1 1 H H62A 0.3562 0.4953 0.1563 0.048 Uiso calc R 1 1 H H62B 0.2740 0.5907 0.1083 0.048 Uiso calc R 1 1 H H62C 0.4008 0.6100 0.1874 0.048 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 0.0205(2) 0.0200(2) 0.0200(2) -0.00170(18) 0.00562(18) 0.00025(18) O1 0.0267(7) 0.0211(6) 0.0264(6) -0.0013(5) 0.0002(5) 0.0043(5) O2 0.0203(6) 0.0203(5) 0.0264(6) -0.0003(5) 0.0069(5) 0.0015(5) O3 0.0278(7) 0.0316(6) 0.0216(6) -0.0048(5) 0.0086(5) -0.0032(5) C11 0.0192(9) 0.0223(8) 0.0202(9) -0.0005(7) 0.0093(7) 0.0025(7) C12 0.0212(9) 0.0224(8) 0.0189(9) -0.0014(7) 0.0072(8) -0.0026(7) C13 0.0201(9) 0.0222(8) 0.0202(9) -0.0031(7) 0.0079(8) 0.0019(7) N14 0.0218(8) 0.0241(7) 0.0189(7) -0.0020(6) 0.0072(6) 0.0017(6) C15 0.0164(9) 0.0224(8) 0.0184(8) -0.0025(7) 0.0069(7) 0.0034(7) C16 0.0163(9) 0.0208(8) 0.0182(8) 0.0013(6) 0.0062(7) 0.0032(6) C21 0.0192(9) 0.0248(8) 0.0197(9) -0.0030(7) 0.0071(8) 0.0022(7) N22 0.0253(8) 0.0261(7) 0.0269(8) 0.0017(6) 0.0087(7) 0.0025(6) C23 0.0293(11) 0.0248(9) 0.0349(10) 0.0012(8) 0.0139(9) 0.0029(7) C24 0.0203(10) 0.0293(9) 0.0350(10) 0.0028(7) 0.0070(8) 0.0124(8) C25 0.0211(10) 0.0368(10) 0.0271(10) -0.0033(8) 0.0021(8) 0.0060(8) C26 0.0226(10) 0.0262(9) 0.0236(9) -0.0025(7) 0.0048(8) 0.0001(7) C31 0.0166(9) 0.0228(9) 0.0194(9) -0.0028(7) 0.0073(8) 0.0028(7) N32 0.0215(8) 0.0285(7) 0.0246(8) -0.0009(6) 0.0057(6) -0.0042(6) C33 0.0219(10) 0.0310(9) 0.0323(10) -0.0005(8) 0.0093(8) -0.0069(8) C34 0.0291(10) 0.0322(9) 0.0263(10) -0.0074(8) 0.0141(9) -0.0106(7) C35 0.0308(11) 0.0379(10) 0.0195(9) -0.0040(8) 0.0038(8) -0.0041(8) C36 0.0243(10) 0.0276(9) 0.0191(9) 0.0010(7) 0.0028(8) 0.0013(7) C41 0.0199(9) 0.0171(8) 0.0198(9) -0.0010(6) 0.0054(8) 0.0011(6) C42 0.0167(9) 0.0273(9) 0.0261(10) 0.0034(7) 0.0066(8) -0.0026(7) C43 0.0246(10) 0.0257(9) 0.0215(9) -0.0001(7) 0.0098(8) -0.0044(7) C44 0.0197(9) 0.0152(7) 0.0216(9) -0.0007(7) 0.0072(7) 0.0020(6) C45 0.0165(9) 0.0192(8) 0.0231(9) 0.0022(7) 0.0063(8) 0.0022(7) C46 0.0227(9) 0.0156(7) 0.0205(9) 0.0016(7) 0.0093(8) -0.0009(6) C51 0.0262(10) 0.0300(9) 0.0292(10) 0.0014(8) 0.0011(8) 0.0062(8) C52 0.0260(10) 0.0269(9) 0.0275(9) 0.0029(7) 0.0070(8) 0.0034(7) C61 0.0239(10) 0.0180(8) 0.0294(9) -0.0006(7) 0.0087(8) 0.0017(7) C62 0.0351(11) 0.0312(9) 0.0287(10) -0.0044(8) 0.0115(9) 0.0024(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 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 O3 P1 O1 116.57(6) O3 P1 O2 114.70(6) O1 P1 O2 101.19(6) O3 P1 C44 113.77(7) O1 P1 C44 102.29(6) O2 P1 C44 106.77(6) C51 O1 P1 121.89(9) C61 O2 P1 118.05(9) C16 C11 C12 117.61(14) C16 C11 C41 119.81(13) C12 C11 C41 122.57(13) C11 C12 C13 119.64(14) C11 C12 H12 120.2 C13 C12 H12 120.2 N14 C13 C12 122.12(14) N14 C13 C21 116.23(13) C12 C13 C21 121.62(13) C15 N14 C13 118.11(13) N14 C15 C16 122.29(13) N14 C15 C31 117.10(13) C16 C15 C31 120.59(13) C11 C16 C15 120.22(13) C11 C16 H16 119.9 C15 C16 H16 119.9 N22 C21 C26 122.35(14) N22 C21 C13 116.81(13) C26 C21 C13 120.83(14) C23 N22 C21 116.92(13) N22 C23 C24 124.10(15) N22 C23 H23 117.9 C24 C23 H23 117.9 C25 C24 C23 118.39(15) C25 C24 H24 120.8 C23 C24 H24 120.8 C26 C25 C24 118.71(15) C26 C25 H25 120.6 C24 C25 H25 120.6 C25 C26 C21 119.51(15) C25 C26 H26 120.2 C21 C26 H26 120.2 N32 C31 C36 122.19(14) N32 C31 C15 116.16(13) C36 C31 C15 121.60(13) C33 N32 C31 117.64(13) N32 C33 C34 123.48(15) N32 C33 H33 118.3 C34 C33 H33 118.3 C35 C34 C33 117.94(15) C35 C34 H34 121.0 C33 C34 H34 121.0 C34 C35 C36 119.57(15) C34 C35 H35 120.2 C36 C35 H35 120.2 C35 C36 C31 119.17(15) C35 C36 H36 120.4 C31 C36 H36 120.4 C42 C41 C46 118.52(14) C42 C41 C11 121.62(14) C46 C41 C11 119.86(13) C43 C42 C41 120.96(14) C43 C42 H42 119.5 C41 C42 H42 119.5 C42 C43 C44 120.62(14) C42 C43 H43 119.7 C44 C43 H43 119.7 C43 C44 C45 118.44(14) C43 C44 P1 121.22(11) C45 C44 P1 120.34(12) C46 C45 C44 120.79(14) C46 C45 H45 119.6 C44 C45 H45 119.6 C45 C46 C41 120.65(13) C45 C46 H46 119.7 C41 C46 H46 119.7 O1 C51 C52 107.47(12) O1 C51 H51A 110.2 C52 C51 H51A 110.2 O1 C51 H51B 110.2 C52 C51 H51B 110.2 H51A C51 H51B 108.5 C51 C52 H52A 109.5 C51 C52 H52B 109.5 H52A C52 H52B 109.5 C51 C52 H52C 109.5 H52A C52 H52C 109.5 H52B C52 H52C 109.5 O2 C61 C62 108.30(12) O2 C61 H61A 110.0 C62 C61 H61A 110.0 O2 C61 H61B 110.0 C62 C61 H61B 110.0 H61A C61 H61B 108.4 C61 C62 H62A 109.5 C61 C62 H62B 109.5 H62A C62 H62B 109.5 C61 C62 H62C 109.5 H62A C62 H62C 109.5 H62B C62 H62C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 O3 1.4691(10) P1 O1 1.5734(10) P1 O2 1.5822(10) P1 C44 1.7902(16) O1 C51 1.4553(17) O2 C61 1.4644(16) C11 C16 1.3865(19) C11 C12 1.397(2) C11 C41 1.493(2) C12 C13 1.397(2) C12 H12 0.9500 C13 N14 1.3524(18) C13 C21 1.493(2) N14 C15 1.3520(18) C15 C16 1.387(2) C15 C31 1.4928(19) C16 H16 0.9500 C21 N22 1.3472(18) C21 C26 1.395(2) N22 C23 1.3429(19) C23 C24 1.384(2) C23 H23 0.9500 C24 C25 1.381(2) C24 H24 0.9500 C25 C26 1.379(2) C25 H25 0.9500 C26 H26 0.9500 C31 N32 1.3491(18) C31 C36 1.384(2) N32 C33 1.3414(19) C33 C34 1.389(2) C33 H33 0.9500 C34 C35 1.376(2) C34 H34 0.9500 C35 C36 1.381(2) C35 H35 0.9500 C36 H36 0.9500 C41 C42 1.3972(19) C41 C46 1.397(2) C42 C43 1.389(2) C42 H42 0.9500 C43 C44 1.394(2) C43 H43 0.9500 C44 C45 1.4053(19) C45 C46 1.386(2) C45 H45 0.9500 C46 H46 0.9500 C51 C52 1.503(2) C51 H51A 0.9900 C51 H51B 0.9900 C52 H52A 0.9800 C52 H52B 0.9800 C52 H52C 0.9800 C61 C62 1.503(2) C61 H61A 0.9900 C61 H61B 0.9900 C62 H62A 0.9800 C62 H62B 0.9800 C62 H62C 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 O3 P1 O1 C51 64.82(12) O2 P1 O1 C51 -60.30(12) C44 P1 O1 C51 -170.42(11) O3 P1 O2 C61 59.59(11) O1 P1 O2 C61 -174.05(10) C44 P1 O2 C61 -67.41(11) C16 C11 C12 C13 0.5(2) C41 C11 C12 C13 -178.66(13) C11 C12 C13 N14 0.1(2) C11 C12 C13 C21 178.06(13) C12 C13 N14 C15 -0.6(2) C21 C13 N14 C15 -178.60(12) C13 N14 C15 C16 0.4(2) C13 N14 C15 C31 178.91(12) C12 C11 C16 C15 -0.6(2) C41 C11 C16 C15 178.51(13) N14 C15 C16 C11 0.2(2) C31 C15 C16 C11 -178.24(12) N14 C13 C21 N22 174.58(12) C12 C13 C21 N22 -3.5(2) N14 C13 C21 C26 -4.2(2) C12 C13 C21 C26 177.82(13) C26 C21 N22 C23 1.4(2) C13 C21 N22 C23 -177.27(12) C21 N22 C23 C24 -0.6(2) N22 C23 C24 C25 -0.5(2) C23 C24 C25 C26 0.6(2) C24 C25 C26 C21 0.2(2) N22 C21 C26 C25 -1.3(2) C13 C21 C26 C25 177.38(14) N14 C15 C31 N32 179.95(12) C16 C15 C31 N32 -1.51(19) N14 C15 C31 C36 -2.4(2) C16 C15 C31 C36 176.11(13) C36 C31 N32 C33 0.3(2) C15 C31 N32 C33 177.95(12) C31 N32 C33 C34 -0.9(2) N32 C33 C34 C35 0.7(2) C33 C34 C35 C36 0.1(2) C34 C35 C36 C31 -0.6(2) N32 C31 C36 C35 0.4(2) C15 C31 C36 C35 -177.07(14) C16 C11 C41 C42 145.39(14) C12 C11 C41 C42 -35.5(2) C16 C11 C41 C46 -33.99(19) C12 C11 C41 C46 145.12(14) C46 C41 C42 C43 1.4(2) C11 C41 C42 C43 -177.99(13) C41 C42 C43 C44 -0.1(2) C42 C43 C44 C45 -1.2(2) C42 C43 C44 P1 178.75(11) O3 P1 C44 C43 6.93(14) O1 P1 C44 C43 -119.67(12) O2 P1 C44 C43 134.48(11) O3 P1 C44 C45 -173.13(11) O1 P1 C44 C45 60.27(12) O2 P1 C44 C45 -45.58(13) C43 C44 C45 C46 1.3(2) P1 C44 C45 C46 -178.67(11) C44 C45 C46 C41 0.0(2) C42 C41 C46 C45 -1.3(2) C11 C41 C46 C45 178.09(13) P1 O1 C51 C52 -166.13(10) P1 O2 C61 C62 135.67(11)