# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Heinicke, Joachim' ; Institut fur Chemie und Biochemie Universitat Greifswald Soldmanstrasse 16 17487 Greifswald Germany ; 'Peulecke, Norman' ; Institut fur Chemie und Biochemie Universitat Greifswald Soldmanstrasse 16 17487 Greifswald Germany ; 'Jones, Peter G.' ; Institut fur Anorganische und Analytische Chemie Technische Universitat Braunschweig Postfach 3329 38023 Braunschweig Germany ; _publ_contact_author_name 'ProfD Joachim Heinicke' _publ_contact_author_address ; Department of chemistry and Biochemistry University Greifswald Inorganic Chemistry Soldmannstr. 16 Greifswald 17487 GERMANY ; _publ_contact_author_email HEINICKE@UNI-GREIFSWALD.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Novel alpha-functionally substituted amino acids: diphenylphosphinoglycines ; #============================================================================= data_gravy _database_code_depnum_ccdc_archive 'CCDC 247779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 N O3 P' _chemical_formula_weight 347.38 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6440(11) _cell_length_b 9.7680(8) _cell_length_c 15.2660(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.853(4) _cell_angle_gamma 90.00 _cell_volume 1872.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7699 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 30.3 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w- & \f-scan' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25111 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 30.04 _reflns_number_total 5481 _reflns_number_gt 4084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _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. The methanol molecule is disordered over two positions. ; _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^)+(0.0524P)^2^] 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 'NH free, solvent OH and methyls as rigid groups, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5481 _refine_ls_number_parameters 251 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _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 P P 0.39652(2) 0.15700(3) 0.159983(18) 0.02208(8) Uani 1 1 d . . . O1 O 0.45646(6) 0.49543(8) 0.22624(5) 0.02849(19) Uani 1 1 d . . . O2 O 0.27829(6) 0.47076(8) 0.21810(5) 0.02506(17) Uani 1 1 d . . . N N 0.29291(7) 0.23590(10) 0.30343(6) 0.01934(18) Uani 1 1 d . . . H01 H 0.2737(10) 0.1465(15) 0.2932(9) 0.030(4) Uiso 1 1 d . . . H02 H 0.2383(11) 0.2857(15) 0.2826(9) 0.031(4) Uiso 1 1 d . . . C1 C 0.38545(8) 0.27676(11) 0.25593(7) 0.0198(2) Uani 1 1 d . . . H1 H 0.4518 0.2669 0.2982 0.024 Uiso 1 1 calc R . . C2 C 0.37286(8) 0.42868(12) 0.23124(7) 0.0215(2) Uani 1 1 d . . . C3 C 0.30829(9) 0.25321(12) 0.40362(7) 0.0238(2) Uani 1 1 d . . . C4 C 0.19916(10) 0.22955(14) 0.43423(8) 0.0339(3) Uani 1 1 d . . . H4A H 0.2051 0.2363 0.4987 0.041 Uiso 1 1 calc R . . H4B H 0.1732 0.1383 0.4157 0.041 Uiso 1 1 calc R . . H4C H 0.1491 0.2989 0.4079 0.041 Uiso 1 1 calc R . . C5 C 0.34788(10) 0.39684(13) 0.42826(8) 0.0316(3) Uani 1 1 d . . . H5A H 0.2977 0.4643 0.3997 0.038 Uiso 1 1 calc R . . H5B H 0.4181 0.4105 0.4086 0.038 Uiso 1 1 calc R . . H5C H 0.3533 0.4082 0.4924 0.038 Uiso 1 1 calc R . . C6 C 0.38606(11) 0.14436(14) 0.44133(8) 0.0366(3) Uani 1 1 d . . . H6A H 0.4557 0.1606 0.4211 0.044 Uiso 1 1 calc R . . H6B H 0.3597 0.0539 0.4214 0.044 Uiso 1 1 calc R . . H6C H 0.3931 0.1481 0.5059 0.044 Uiso 1 1 calc R . . C11 C 0.54108(9) 0.14105(12) 0.16276(7) 0.0239(2) Uani 1 1 d . . . C12 C 0.57758(10) 0.01843(13) 0.12956(9) 0.0331(3) Uani 1 1 d . . . H12 H 0.5276 -0.0485 0.1058 0.040 Uiso 1 1 calc R . . C13 C 0.68604(10) -0.00677(14) 0.13085(8) 0.0348(3) Uani 1 1 d . . . H13 H 0.7097 -0.0899 0.1074 0.042 Uiso 1 1 calc R . . C14 C 0.75927(9) 0.08887(14) 0.16623(7) 0.0293(3) Uani 1 1 d . . . H14 H 0.8334 0.0709 0.1685 0.035 Uiso 1 1 calc R . . C15 C 0.72419(9) 0.21156(13) 0.19856(7) 0.0282(3) Uani 1 1 d . . . H15 H 0.7747 0.2778 0.2223 0.034 Uiso 1 1 calc R . . C16 C 0.61609(9) 0.23840(12) 0.19652(7) 0.0249(2) Uani 1 1 d . . . H16 H 0.5931 0.3232 0.2182 0.030 Uiso 1 1 calc R . . C21 C 0.35928(8) 0.26441(11) 0.06293(7) 0.0217(2) Uani 1 1 d . . . C22 C 0.43172(9) 0.32017(13) 0.01074(7) 0.0272(2) Uani 1 1 d . . . H22 H 0.5060 0.3089 0.0278 0.033 Uiso 1 1 calc R . . C23 C 0.39682(10) 0.39178(14) -0.06569(8) 0.0322(3) Uani 1 1 d . . . H23 H 0.4470 0.4283 -0.1010 0.039 Uiso 1 1 calc R . . C24 C 0.28889(10) 0.41013(14) -0.09054(8) 0.0327(3) Uani 1 1 d . . . H24 H 0.2648 0.4606 -0.1423 0.039 Uiso 1 1 calc R . . C25 C 0.21615(10) 0.35454(14) -0.03953(8) 0.0338(3) Uani 1 1 d . . . H25 H 0.1420 0.3666 -0.0567 0.041 Uiso 1 1 calc R . . C26 C 0.25040(9) 0.28164(13) 0.03612(8) 0.0288(3) Uani 1 1 d . . . H26 H 0.1997 0.2430 0.0701 0.035 Uiso 1 1 calc R . . C99 C 0.4864(4) 0.8140(7) 0.3263(3) 0.0385(11) Uani 0.550(5) 1 d PDU A 1 H99A H 0.5545 0.8532 0.3141 0.046 Uiso 0.550(5) 1 calc PR A 1 H99B H 0.4998 0.7360 0.3665 0.046 Uiso 0.550(5) 1 calc PR A 1 H99C H 0.4452 0.8836 0.3537 0.046 Uiso 0.550(5) 1 calc PR A 1 O99 O 0.42867(18) 0.7697(2) 0.24687(19) 0.0375(8) Uani 0.550(5) 1 d PDU A 1 H99 H 0.4436 0.6876 0.2377 0.045 Uiso 0.550(5) 1 calc PR A 1 C99' C 0.4944(6) 0.8311(8) 0.2964(5) 0.0424(14) Uani 0.450(5) 1 d PDU A 2 H99D H 0.4662 0.9227 0.3058 0.051 Uiso 0.450(5) 1 calc PR A 2 H99E H 0.5187 0.8266 0.2378 0.051 Uiso 0.450(5) 1 calc PR A 2 H99F H 0.5544 0.8121 0.3416 0.051 Uiso 0.450(5) 1 calc PR A 2 O99' O 0.41527(19) 0.7348(3) 0.3019(3) 0.0489(12) Uani 0.450(5) 1 d PDU A 2 H99' H 0.4355 0.6586 0.2846 0.059 Uiso 0.450(5) 1 calc PR A 2 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 P 0.02344(14) 0.01904(14) 0.02538(14) -0.00363(12) 0.00958(10) -0.00066(11) O1 0.0300(4) 0.0203(4) 0.0380(4) -0.0011(4) 0.0156(3) -0.0032(3) O2 0.0280(4) 0.0197(4) 0.0287(4) 0.0016(3) 0.0087(3) 0.0028(3) N 0.0197(4) 0.0186(5) 0.0208(4) 0.0013(4) 0.0067(3) 0.0001(4) C1 0.0206(5) 0.0188(5) 0.0215(5) 0.0002(4) 0.0084(4) -0.0009(4) C2 0.0283(5) 0.0184(5) 0.0196(5) -0.0016(4) 0.0104(4) 0.0006(4) C3 0.0288(5) 0.0257(6) 0.0181(5) 0.0002(4) 0.0076(4) -0.0012(5) C4 0.0368(6) 0.0381(7) 0.0301(6) -0.0040(6) 0.0179(5) -0.0067(6) C5 0.0404(7) 0.0313(7) 0.0244(5) -0.0062(5) 0.0090(5) -0.0066(6) C6 0.0425(7) 0.0375(7) 0.0292(6) 0.0082(6) 0.0014(5) 0.0041(6) C11 0.0258(5) 0.0226(6) 0.0245(5) -0.0009(4) 0.0084(4) 0.0034(4) C12 0.0311(6) 0.0276(7) 0.0419(7) -0.0104(6) 0.0090(5) 0.0027(5) C13 0.0361(6) 0.0313(7) 0.0387(7) -0.0037(6) 0.0123(5) 0.0120(6) C14 0.0257(5) 0.0380(7) 0.0254(5) 0.0044(5) 0.0074(4) 0.0098(5) C15 0.0262(5) 0.0334(7) 0.0254(5) 0.0004(5) 0.0051(4) 0.0002(5) C16 0.0271(5) 0.0232(6) 0.0256(5) -0.0015(4) 0.0079(4) 0.0023(5) C21 0.0231(5) 0.0216(5) 0.0214(5) -0.0066(4) 0.0071(4) -0.0017(4) C22 0.0247(5) 0.0312(6) 0.0268(5) -0.0024(5) 0.0073(4) -0.0034(5) C23 0.0390(7) 0.0332(7) 0.0256(6) -0.0010(5) 0.0096(5) -0.0052(6) C24 0.0449(7) 0.0298(7) 0.0227(5) -0.0051(5) 0.0011(5) 0.0032(6) C25 0.0289(6) 0.0391(7) 0.0324(6) -0.0100(6) -0.0004(5) 0.0043(5) C26 0.0239(5) 0.0326(7) 0.0312(6) -0.0061(5) 0.0081(4) -0.0016(5) C99 0.0227(15) 0.046(3) 0.047(2) -0.015(2) 0.0043(16) -0.0011(15) O99 0.0359(11) 0.0242(10) 0.0490(15) -0.0089(9) -0.0096(9) 0.0034(8) C99' 0.030(2) 0.030(2) 0.068(4) -0.006(3) 0.011(3) -0.0045(16) O99' 0.0403(13) 0.0279(13) 0.085(3) -0.0176(16) 0.0343(13) -0.0076(10) _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 P C11 1.8299(11) . ? P C21 1.8306(12) . ? P C1 1.8927(11) . ? O1 C2 1.2520(13) . ? O2 C2 1.2577(13) . ? N C1 1.5021(13) . ? N C3 1.5281(13) . ? C1 C2 1.5347(15) . ? C3 C6 1.5145(17) . ? C3 C5 1.5216(17) . ? C3 C4 1.5263(15) . ? C11 C16 1.3974(16) . ? C11 C12 1.4002(16) . ? C12 C13 1.3911(16) . ? C13 C14 1.3792(18) . ? C14 C15 1.3888(18) . ? C15 C16 1.3884(15) . ? C21 C22 1.3945(15) . ? C21 C26 1.3989(15) . ? C22 C23 1.3865(17) . ? C23 C24 1.3837(17) . ? C24 C25 1.3850(18) . ? C25 C26 1.3817(17) . ? C99 O99 1.407(5) . ? C99' O99' 1.383(6) . ? 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 C11 P C21 103.14(5) . . ? C11 P C1 101.57(5) . . ? C21 P C1 103.68(5) . . ? C1 N C3 116.12(8) . . ? N C1 C2 108.16(8) . . ? N C1 P 110.07(7) . . ? C2 C1 P 115.00(7) . . ? O1 C2 O2 127.85(11) . . ? O1 C2 C1 117.06(9) . . ? O2 C2 C1 115.09(9) . . ? C6 C3 C5 111.95(10) . . ? C6 C3 C4 110.30(10) . . ? C5 C3 C4 110.29(9) . . ? C6 C3 N 107.58(9) . . ? C5 C3 N 110.38(9) . . ? C4 C3 N 106.14(9) . . ? C16 C11 C12 118.49(10) . . ? C16 C11 P 125.64(8) . . ? C12 C11 P 115.85(9) . . ? C13 C12 C11 120.88(12) . . ? C14 C13 C12 120.02(12) . . ? C13 C14 C15 119.72(11) . . ? C16 C15 C14 120.68(11) . . ? C15 C16 C11 120.19(11) . . ? C22 C21 C26 118.45(11) . . ? C22 C21 P 124.28(9) . . ? C26 C21 P 117.05(8) . . ? C23 C22 C21 120.87(11) . . ? C24 C23 C22 120.03(11) . . ? C23 C24 C25 119.63(12) . . ? C26 C25 C24 120.61(11) . . ? C25 C26 C21 120.39(11) . . ? 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 C3 N C1 C2 -89.92(11) . . . . ? C3 N C1 P 143.70(8) . . . . ? C11 P C1 N -142.58(7) . . . . ? C21 P C1 N 110.65(8) . . . . ? C11 P C1 C2 94.99(8) . . . . ? C21 P C1 C2 -11.78(8) . . . . ? N C1 C2 O1 150.70(9) . . . . ? P C1 C2 O1 -85.84(10) . . . . ? N C1 C2 O2 -29.53(12) . . . . ? P C1 C2 O2 93.92(9) . . . . ? C1 N C3 C6 -71.56(12) . . . . ? C1 N C3 C5 50.86(12) . . . . ? C1 N C3 C4 170.37(9) . . . . ? C21 P C11 C16 80.83(11) . . . . ? C1 P C11 C16 -26.37(11) . . . . ? C21 P C11 C12 -100.68(10) . . . . ? C1 P C11 C12 152.12(9) . . . . ? C16 C11 C12 C13 0.60(18) . . . . ? P C11 C12 C13 -178.01(10) . . . . ? C11 C12 C13 C14 0.88(19) . . . . ? C12 C13 C14 C15 -1.53(18) . . . . ? C13 C14 C15 C16 0.71(17) . . . . ? C14 C15 C16 C11 0.80(17) . . . . ? C12 C11 C16 C15 -1.43(17) . . . . ? P C11 C16 C15 177.03(9) . . . . ? C11 P C21 C22 -2.50(11) . . . . ? C1 P C21 C22 103.09(10) . . . . ? C11 P C21 C26 172.15(9) . . . . ? C1 P C21 C26 -82.26(9) . . . . ? C26 C21 C22 C23 0.39(17) . . . . ? P C21 C22 C23 174.97(9) . . . . ? C21 C22 C23 C24 0.77(19) . . . . ? C22 C23 C24 C25 -1.15(19) . . . . ? C23 C24 C25 C26 0.35(19) . . . . ? C24 C25 C26 C21 0.82(19) . . . . ? C22 C21 C26 C25 -1.18(17) . . . . ? P C21 C26 C25 -176.16(9) . . . . ? 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 N H01 O2 0.914(14) 1.839(15) 2.7486(13) 172.7(13) 2_545 N H02 O99 0.873(14) 2.111(14) 2.834(2) 139.8(12) 2_545 N H02 O99' 0.873(14) 2.256(14) 2.916(4) 132.4(12) 2_545 O99 H99 O1 0.84 1.89 2.725(2) 170.3 . O99' H99' O1 0.84 1.86 2.686(2) 167.5 . C23 H23 O1 0.95 2.50 3.4274(14) 164.9 3_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.379 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.041 # end of cif file