# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'D. Vaughan Griffiths' _publ_contact_author_address ; School of Biological and Chemical Sciences Queen Mary & Westfield Colleges, University of London Mile End Road London E1 4NS UNITED KINGDOM ; _publ_contact_author_email D.V.GRIFFITHS@QMUL.AC.UK _publ_section_title ; Electron-rich heteroaroylphosphonates and their reaction with trimethyl phosphite ; loop_ _publ_author_name 'D. Griffiths' 'Mohamad J. Al-Jeboori' 'Yuen-Ki Cheong.' 'Philip Duncanson' ; J.E.Harris ; 'Michael C. Salt' 'Helen V. Taylor' data_hvd-04-303 _database_code_depnum_ccdc_archive 'CCDC 648419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 N4 O7 P' _chemical_formula_weight 368.24 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2246(2) _cell_length_b 8.6176(2) _cell_length_c 11.5999(3) _cell_angle_alpha 69.5210(10) _cell_angle_beta 88.2020(10) _cell_angle_gamma 85.0020(10) _cell_volume 767.27(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3448 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9432 _exptl_absorpt_correction_T_max 0.9820 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M.,2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14406 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3510 _reflns_number_gt 3217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'DIRDIF-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) &PLUTON (Spek,A.L.,1990)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0864P)^2^+0.2257P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3510 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.78707(16) -0.53026(17) -0.02156(13) 0.0167(3) Uani 1 1 d . . . C2 C 0.69806(17) -0.62689(17) 0.07843(13) 0.0174(3) Uani 1 1 d . . . H2 H 0.6982 -0.7433 0.0968 0.021 Uiso 1 1 calc R . . C3 C 0.61032(17) -0.55143(17) 0.14972(12) 0.0166(3) Uani 1 1 d . . . H3 H 0.5489 -0.6173 0.2171 0.020 Uiso 1 1 calc R . . C4 C 0.60843(16) -0.37826(17) 0.12601(12) 0.0150(3) Uani 1 1 d . . . C5 C 0.69588(16) -0.28515(16) 0.02061(12) 0.0150(3) Uani 1 1 d . . . C6 C 0.78425(16) -0.36062(17) -0.05244(12) 0.0163(3) Uani 1 1 d . . . H6 H 0.8419 -0.2960 -0.1227 0.020 Uiso 1 1 calc R . . C7 C 0.36038(16) -0.34362(16) 0.36718(12) 0.0158(3) Uani 1 1 d . . . H7 H 0.3830 -0.2361 0.3643 0.019 Uiso 1 1 calc R . . C8 C 0.25249(17) -0.44266(17) 0.45931(13) 0.0181(3) Uani 1 1 d . . . H8 H 0.2291 -0.5463 0.4545 0.022 Uiso 1 1 calc R . . C9 C 0.18252(17) -0.39910(17) 0.55156(13) 0.0178(3) Uani 1 1 d . . . H9 H 0.1121 -0.4723 0.6068 0.021 Uiso 1 1 calc R . . C10 C 0.20946(16) -0.24868(17) 0.56975(12) 0.0163(3) Uani 1 1 d . . . C11 C 0.23603(17) -0.12368(17) 0.58700(12) 0.0173(3) Uani 1 1 d . . . C12 C 0.27267(18) 0.19466(17) 0.36516(12) 0.0192(3) Uani 1 1 d . . . H12A H 0.3082 0.1123 0.3270 0.029 Uiso 1 1 calc R . . H12B H 0.2903 0.3062 0.3076 0.029 Uiso 1 1 calc R . . H12C H 0.1564 0.1878 0.3857 0.029 Uiso 1 1 calc R . . C13 C 0.03495(18) 0.0947(2) 0.72396(14) 0.0241(3) Uani 1 1 d . . . H13A H -0.0226 0.0043 0.7157 0.036 Uiso 1 1 calc R . . H13B H -0.0447 0.1833 0.7295 0.036 Uiso 1 1 calc R . . H13C H 0.1019 0.0524 0.7986 0.036 Uiso 1 1 calc R . . N1 N 0.89006(14) -0.61071(15) -0.09240(11) 0.0192(3) Uani 1 1 d . . . N2 N 0.69775(14) -0.10570(14) -0.01754(11) 0.0163(2) Uani 1 1 d . . . N3 N 0.52472(14) -0.30981(14) 0.20215(10) 0.0163(2) Uani 1 1 d . . . H3A H 0.5348 -0.2062 0.1956 0.020 Uiso 1 1 calc R . . N4 N 0.42447(14) -0.40694(14) 0.28928(11) 0.0166(2) Uani 1 1 d . . . O1 O 0.95233(13) -0.52222(14) -0.18863(10) 0.0261(3) Uani 1 1 d . . . O2 O 0.91307(14) -0.76269(14) -0.05104(11) 0.0277(3) Uani 1 1 d . . . O3 O 0.65697(14) -0.03873(13) 0.05834(10) 0.0229(2) Uani 1 1 d . . . O4 O 0.73842(14) -0.02866(13) -0.12360(9) 0.0237(2) Uani 1 1 d . . . O5 O 0.41908(12) 0.01887(12) 0.70337(9) 0.0196(2) Uani 1 1 d . . . O6 O 0.36628(12) 0.16151(12) 0.47664(9) 0.0170(2) Uani 1 1 d . . . O7 O 0.13886(12) 0.16017(12) 0.61768(9) 0.0186(2) Uani 1 1 d . . . P1 P 0.29940(4) 0.05462(4) 0.60481(3) 0.01382(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(6) 0.0227(7) 0.0161(6) -0.0111(5) -0.0001(5) 0.0008(5) C2 0.0170(6) 0.0184(6) 0.0175(6) -0.0074(5) -0.0016(5) 0.0010(5) C3 0.0165(6) 0.0177(6) 0.0150(6) -0.0049(5) 0.0013(5) -0.0009(5) C4 0.0133(6) 0.0186(6) 0.0134(6) -0.0060(5) -0.0006(5) -0.0008(5) C5 0.0150(6) 0.0175(6) 0.0136(6) -0.0063(5) -0.0004(5) -0.0022(5) C6 0.0145(6) 0.0231(7) 0.0122(6) -0.0071(5) -0.0001(5) -0.0026(5) C7 0.0167(6) 0.0144(6) 0.0173(6) -0.0066(5) 0.0021(5) -0.0021(5) C8 0.0212(7) 0.0151(6) 0.0195(7) -0.0077(5) 0.0043(5) -0.0043(5) C9 0.0193(7) 0.0161(6) 0.0188(7) -0.0066(5) 0.0052(5) -0.0043(5) C10 0.0164(6) 0.0192(6) 0.0128(6) -0.0055(5) 0.0037(5) -0.0005(5) C11 0.0194(7) 0.0180(6) 0.0149(6) -0.0063(5) 0.0017(5) -0.0021(5) C12 0.0226(7) 0.0209(7) 0.0145(6) -0.0068(5) -0.0004(5) -0.0008(5) C13 0.0203(7) 0.0326(8) 0.0195(7) -0.0102(6) 0.0076(6) -0.0014(6) N1 0.0156(6) 0.0263(6) 0.0202(6) -0.0141(5) 0.0008(4) -0.0010(5) N2 0.0168(5) 0.0185(6) 0.0141(5) -0.0061(4) 0.0021(4) -0.0039(4) N3 0.0187(6) 0.0155(5) 0.0153(6) -0.0061(4) 0.0048(4) -0.0038(4) N4 0.0176(6) 0.0161(5) 0.0157(6) -0.0049(4) 0.0041(4) -0.0028(4) O1 0.0258(6) 0.0346(6) 0.0179(5) -0.0105(5) 0.0066(4) 0.0011(4) O2 0.0285(6) 0.0232(5) 0.0376(7) -0.0187(5) 0.0079(5) -0.0035(4) O3 0.0321(6) 0.0208(5) 0.0202(5) -0.0121(4) 0.0079(4) -0.0073(4) O4 0.0323(6) 0.0216(5) 0.0163(5) -0.0049(4) 0.0079(4) -0.0074(4) O5 0.0210(5) 0.0240(5) 0.0166(5) -0.0103(4) -0.0008(4) -0.0018(4) O6 0.0179(5) 0.0185(5) 0.0154(5) -0.0065(4) 0.0013(4) -0.0033(4) O7 0.0187(5) 0.0188(5) 0.0190(5) -0.0082(4) 0.0045(4) 0.0006(4) P1 0.0150(2) 0.0147(2) 0.0137(2) -0.00738(14) 0.00173(13) -0.00155(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.376(2) . ? C1 C2 1.3970(19) . ? C1 N1 1.4581(17) . ? C2 C3 1.3729(19) . ? C2 H2 0.9500 . ? C3 C4 1.4184(19) . ? C3 H3 0.9500 . ? C4 N3 1.3630(17) . ? C4 C5 1.4194(18) . ? C5 C6 1.3907(18) . ? C5 N2 1.4534(17) . ? C6 H6 0.9500 . ? C7 N4 1.2873(17) . ? C7 C8 1.4465(18) . ? C7 H7 0.9500 . ? C8 C9 1.3498(19) . ? C8 H8 0.9500 . ? C9 C10 1.4207(19) . ? C9 H9 0.9500 . ? C10 C11 1.201(2) . ? C11 P1 1.7446(14) . ? C12 O6 1.4534(16) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O7 1.4490(16) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 O2 1.2264(17) . ? N1 O1 1.2355(16) . ? N2 O4 1.2279(15) . ? N2 O3 1.2342(15) . ? N3 N4 1.3703(15) . ? N3 H3A 0.8800 . ? O5 P1 1.4636(10) . ? O6 P1 1.5621(10) . ? O7 P1 1.5705(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.43(12) . . ? C6 C1 N1 118.97(12) . . ? C2 C1 N1 119.57(12) . . ? C3 C2 C1 119.16(12) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 122.09(12) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N3 C4 C3 120.03(12) . . ? N3 C4 C5 123.61(12) . . ? C3 C4 C5 116.35(12) . . ? C6 C5 C4 121.80(12) . . ? C6 C5 N2 116.15(11) . . ? C4 C5 N2 122.04(12) . . ? C1 C6 C5 119.06(12) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? N4 C7 C8 117.37(12) . . ? N4 C7 H7 121.3 . . ? C8 C7 H7 121.3 . . ? C9 C8 C7 124.98(12) . . ? C9 C8 H8 117.5 . . ? C7 C8 H8 117.5 . . ? C8 C9 C10 122.98(12) . . ? C8 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 178.18(15) . . ? C10 C11 P1 172.73(13) . . ? O6 C12 H12A 109.5 . . ? O6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O7 C13 H13A 109.5 . . ? O7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 N1 O1 123.79(12) . . ? O2 N1 C1 117.80(12) . . ? O1 N1 C1 118.38(12) . . ? O4 N2 O3 123.49(11) . . ? O4 N2 C5 118.39(11) . . ? O3 N2 C5 118.11(11) . . ? C4 N3 N4 118.10(11) . . ? C4 N3 H3A 120.9 . . ? N4 N3 H3A 120.9 . . ? C7 N4 N3 116.19(11) . . ? C12 O6 P1 120.80(8) . . ? C13 O7 P1 119.03(9) . . ? O5 P1 O6 112.51(6) . . ? O5 P1 O7 115.53(6) . . ? O6 P1 O7 102.57(5) . . ? O5 P1 C11 113.32(6) . . ? O6 P1 C11 106.13(6) . . ? O7 P1 C11 105.77(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.2(2) . . . . ? N1 C1 C2 C3 175.54(12) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 N3 -177.42(13) . . . . ? C2 C3 C4 C5 3.0(2) . . . . ? N3 C4 C5 C6 177.83(13) . . . . ? C3 C4 C5 C6 -2.62(19) . . . . ? N3 C4 C5 N2 -2.5(2) . . . . ? C3 C4 C5 N2 177.10(12) . . . . ? C2 C1 C6 C5 2.6(2) . . . . ? N1 C1 C6 C5 -175.19(12) . . . . ? C4 C5 C6 C1 -0.1(2) . . . . ? N2 C5 C6 C1 -179.80(12) . . . . ? N4 C7 C8 C9 176.18(14) . . . . ? C7 C8 C9 C10 -0.9(2) . . . . ? C8 C9 C10 C11 -86(5) . . . . ? C9 C10 C11 P1 53(5) . . . . ? C6 C1 N1 O2 167.59(13) . . . . ? C2 C1 N1 O2 -10.20(19) . . . . ? C6 C1 N1 O1 -10.60(19) . . . . ? C2 C1 N1 O1 171.61(12) . . . . ? C6 C5 N2 O4 18.19(18) . . . . ? C4 C5 N2 O4 -161.54(12) . . . . ? C6 C5 N2 O3 -162.40(12) . . . . ? C4 C5 N2 O3 17.87(19) . . . . ? C3 C4 N3 N4 -9.60(19) . . . . ? C5 C4 N3 N4 169.94(12) . . . . ? C8 C7 N4 N3 179.29(12) . . . . ? C4 N3 N4 C7 173.28(12) . . . . ? C12 O6 P1 O5 173.18(9) . . . . ? C12 O6 P1 O7 -62.04(10) . . . . ? C12 O6 P1 C11 48.71(11) . . . . ? C13 O7 P1 O5 -61.07(12) . . . . ? C13 O7 P1 O6 176.16(10) . . . . ? C13 O7 P1 C11 65.14(12) . . . . ? C10 C11 P1 O5 -70.4(10) . . . . ? C10 C11 P1 O6 53.6(10) . . . . ? C10 C11 P1 O7 162.0(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O3 0.88 2.04 2.6505(15) 125.3 . N3 H3A O5 0.88 2.36 3.1397(15) 147.3 2_656 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.405 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.079