data_ami1 _publ_requested_journal 'Phosphorus, Sulfur and Silica' _publ_contact_author_name 'Voronina J.K.' _publ_contact_author_address ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; _publ_contact_author_email ;juliavoronina@mail.ru ; loop_ _publ_author_name _publ_author_address 'Voronina J.K.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Vagapova, L.I.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Amirova, L.R.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Syakaev, V.V.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Krivolapov, D.B.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Burilov, A.R.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; ' Dontsova, O.A.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; 'Pudovik, M.A.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; 'Synashin, O.G.' ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; _audit_creation_method SHELXL-97 _chemical_name_systematic Diethyl((3,5-di-tert-butyl-4-hydroxyphenyl)((2,2-dimethoxyethyl)amino)methyl)phosphonate _chemical_name_common Diethyl((3,5-di-tert-butyl-4-hydroxyphenyl)((2,2-dimethoxyethyl)amino)methyl)phosphonate _chemical_formula_moiety 'C23 H42 N O6 P' _chemical_formula_sum 'C23 H42 N O6 P' _chemical_melting_point ? _exptl_crystal_description prizm _exptl_crystal_colour colorless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 459.55 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/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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' _cell_length_a 10.130(4) _cell_length_b 13.961(6) _cell_length_c 18.869(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.006(6) _cell_angle_gamma 90.00 _cell_volume 2619.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min -3 _cell_measurement_theta_max 52 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19966 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5145 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.1829P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5145 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1935 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 P1 P 1.18547(7) -0.02923(6) 0.13729(4) 0.0303(2) Uani 1 1 d . . . O6 O 0.55289(17) 0.05910(15) 0.13788(10) 0.0336(5) Uani 1 1 d . . . H6 H 0.5177 0.0142 0.1574 0.050 Uiso 1 1 calc R . . O1 O 1.33180(19) -0.03724(17) 0.15765(12) 0.0461(6) Uani 1 1 d . . . C16 C 0.7569(2) -0.01883(18) 0.20193(13) 0.0218(6) Uani 1 1 d . . . N1 N 1.1779(2) 0.01545(16) 0.27336(12) 0.0288(6) Uani 1 1 d . . . H1 H 1.2212 -0.0391 0.2831 0.035 Uiso 1 1 calc R . . C14 C 0.7601(2) 0.12576(18) 0.12765(13) 0.0227(6) Uani 1 1 d . . . C17 C 0.8968(2) -0.01811(18) 0.21507(14) 0.0227(6) Uani 1 1 d . . . H17 H 0.9442 -0.0668 0.2447 0.027 Uiso 1 1 calc R . . O3 O 1.10894(19) -0.12687(14) 0.13178(10) 0.0358(5) Uani 1 1 d . . . C7 C 1.1217(2) 0.0474(2) 0.20017(14) 0.0278(6) Uani 1 1 d . . . H7 H 1.1552 0.1138 0.1944 0.033 Uiso 1 1 calc R . . C13 C 0.8999(2) 0.12252(18) 0.14417(13) 0.0228(6) Uani 1 1 d . . . H13 H 0.9496 0.1712 0.1257 0.027 Uiso 1 1 calc R . . O4 O 1.3336(2) 0.01427(15) 0.41920(12) 0.0479(6) Uani 1 1 d . . . C15 C 0.6900(2) 0.05305(19) 0.15683(13) 0.0227(6) Uani 1 1 d . . . C12 C 0.9692(2) 0.05095(19) 0.18651(13) 0.0228(6) Uani 1 1 d . . . O2 O 1.1275(2) 0.01219(17) 0.06155(12) 0.0470(6) Uani 1 1 d . . . C22 C 0.6825(3) -0.0961(2) 0.23751(14) 0.0274(6) Uani 1 1 d . . . C23 C 0.5997(3) -0.1616(2) 0.18005(16) 0.0356(7) Uani 1 1 d . . . H23A H 0.5512 -0.2089 0.2037 0.053 Uiso 1 1 calc R . . H23B H 0.6600 -0.1946 0.1532 0.053 Uiso 1 1 calc R . . H23C H 0.5350 -0.1229 0.1466 0.053 Uiso 1 1 calc R . . C24 C 0.5955(3) -0.0479(2) 0.28573(15) 0.0344(7) Uani 1 1 d . . . H24A H 0.6538 -0.0163 0.3265 0.052 Uiso 1 1 calc R . . H24B H 0.5405 -0.0964 0.3039 0.052 Uiso 1 1 calc R . . H24C H 0.5367 -0.0002 0.2575 0.052 Uiso 1 1 calc R . . C18 C 0.6864(3) 0.20594(19) 0.07990(14) 0.0278(6) Uani 1 1 d . . . C8 C 1.1551(3) 0.0828(2) 0.32839(15) 0.0367(7) Uani 1 1 d . . . H8A H 1.0585 0.0997 0.3204 0.044 Uiso 1 1 calc R . . H8B H 1.2068 0.1421 0.3248 0.044 Uiso 1 1 calc R . . C25 C 0.7814(3) -0.1622(2) 0.28660(17) 0.0392(8) Uani 1 1 d . . . H25A H 0.8348 -0.1245 0.3257 0.059 Uiso 1 1 calc R . . H25B H 0.8414 -0.1928 0.2583 0.059 Uiso 1 1 calc R . . H25C H 0.7312 -0.2116 0.3072 0.059 Uiso 1 1 calc R . . C19 C 0.6025(3) 0.1641(2) 0.01049(14) 0.0369(7) Uani 1 1 d . . . H19A H 0.5362 0.1192 0.0229 0.055 Uiso 1 1 calc R . . H19B H 0.6618 0.1304 -0.0166 0.055 Uiso 1 1 calc R . . H19C H 0.5560 0.2161 -0.0191 0.055 Uiso 1 1 calc R . . C3 C 1.2016(3) 0.0585(2) 0.01347(19) 0.0481(9) Uani 1 1 d . . . H3A H 1.1729 0.0320 -0.0357 0.058 Uiso 1 1 calc R . . H3B H 1.2986 0.0448 0.0294 0.058 Uiso 1 1 calc R . . O5 O 1.1630(3) 0.10791(18) 0.44979(12) 0.0617(7) Uani 1 1 d . . . C9 C 1.1972(3) 0.0405(2) 0.40195(16) 0.0411(8) Uani 1 1 d . . . H9 H 1.1419 -0.0182 0.4047 0.049 Uiso 1 1 calc R . . C21 C 0.5960(3) 0.2631(2) 0.12079(16) 0.0409(8) Uani 1 1 d . . . H21A H 0.5242 0.2216 0.1313 0.061 Uiso 1 1 calc R . . H21B H 0.5564 0.3172 0.0911 0.061 Uiso 1 1 calc R . . H21C H 0.6495 0.2871 0.1661 0.061 Uiso 1 1 calc R . . C20 C 0.7857(3) 0.2764(2) 0.05678(18) 0.0448(8) Uani 1 1 d . . . H20A H 0.7359 0.3272 0.0273 0.067 Uiso 1 1 calc R . . H20B H 0.8427 0.2425 0.0285 0.067 Uiso 1 1 calc R . . H20C H 0.8420 0.3046 0.0997 0.067 Uiso 1 1 calc R . . C5 C 1.1433(4) -0.2016(2) 0.18524(18) 0.0555(10) Uani 1 1 d . . . H5A H 1.0624 -0.2188 0.2047 0.067 Uiso 1 1 calc R . . H5B H 1.2119 -0.1771 0.2257 0.067 Uiso 1 1 calc R . . C10 C 1.4269(4) 0.0914(3) 0.4199(2) 0.0639(11) Uani 1 1 d . . . H10A H 1.4295 0.1104 0.3702 0.096 Uiso 1 1 calc R . . H10B H 1.5166 0.0706 0.4441 0.096 Uiso 1 1 calc R . . H10C H 1.3984 0.1461 0.4459 0.096 Uiso 1 1 calc R . . C4 C 1.1809(5) 0.1618(3) 0.0113(3) 0.0906(16) Uani 1 1 d . . . H4A H 1.0844 0.1756 0.0004 0.136 Uiso 1 1 calc R . . H4B H 1.2240 0.1897 -0.0262 0.136 Uiso 1 1 calc R . . H4C H 1.2207 0.1895 0.0582 0.136 Uiso 1 1 calc R . . C6 C 1.1948(4) -0.2867(3) 0.1556(2) 0.0622(11) Uani 1 1 d . . . H6A H 1.1317 -0.3069 0.1121 0.093 Uiso 1 1 calc R . . H6B H 1.2052 -0.3382 0.1915 0.093 Uiso 1 1 calc R . . H6C H 1.2823 -0.2724 0.1431 0.093 Uiso 1 1 calc R . . C11 C 1.1818(6) 0.0739(4) 0.5221(2) 0.0995(18) Uani 1 1 d . . . H11A H 1.1378 0.0115 0.5229 0.149 Uiso 1 1 calc R . . H11B H 1.1423 0.1196 0.5516 0.149 Uiso 1 1 calc R . . H11C H 1.2782 0.0673 0.5416 0.149 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0164(4) 0.0422(5) 0.0325(4) 0.0048(3) 0.0054(3) 0.0009(3) O6 0.0147(9) 0.0435(12) 0.0424(12) 0.0124(9) 0.0050(8) 0.0057(8) O1 0.0179(11) 0.0667(16) 0.0546(14) 0.0030(11) 0.0091(10) 0.0038(10) C16 0.0194(13) 0.0256(14) 0.0211(13) -0.0044(11) 0.0055(10) -0.0025(11) N1 0.0269(12) 0.0251(12) 0.0301(13) 0.0001(10) -0.0053(10) 0.0043(10) C14 0.0229(13) 0.0245(14) 0.0205(13) -0.0010(11) 0.0036(10) 0.0032(11) C17 0.0181(13) 0.0261(14) 0.0231(13) 0.0006(11) 0.0015(10) 0.0038(11) O3 0.0322(11) 0.0370(12) 0.0378(12) -0.0021(9) 0.0054(9) 0.0010(9) C7 0.0170(13) 0.0299(15) 0.0340(16) 0.0051(12) -0.0018(11) -0.0041(11) C13 0.0250(14) 0.0207(13) 0.0236(13) -0.0003(11) 0.0066(11) -0.0027(11) O4 0.0551(15) 0.0317(12) 0.0463(13) 0.0002(10) -0.0176(11) 0.0038(11) C15 0.0136(12) 0.0325(15) 0.0214(13) -0.0028(11) 0.0023(10) 0.0042(11) C12 0.0173(13) 0.0265(14) 0.0241(14) -0.0023(11) 0.0026(10) -0.0001(10) O2 0.0333(12) 0.0722(16) 0.0375(13) 0.0206(11) 0.0118(10) 0.0029(11) C22 0.0224(14) 0.0306(15) 0.0302(15) 0.0051(12) 0.0080(11) -0.0016(11) C23 0.0251(15) 0.0342(17) 0.0469(18) -0.0024(14) 0.0054(13) -0.0042(13) C24 0.0322(16) 0.0395(17) 0.0343(16) 0.0049(13) 0.0135(13) -0.0031(13) C18 0.0313(15) 0.0266(15) 0.0255(14) 0.0019(12) 0.0056(11) 0.0100(12) C8 0.0358(16) 0.0309(16) 0.0377(17) -0.0060(13) -0.0071(13) 0.0024(13) C25 0.0358(17) 0.0386(18) 0.0431(18) 0.0148(14) 0.0074(14) -0.0031(14) C19 0.0433(18) 0.0427(18) 0.0230(15) 0.0035(13) 0.0018(13) 0.0156(14) C3 0.048(2) 0.051(2) 0.051(2) 0.0089(17) 0.0219(16) 0.0005(17) O5 0.091(2) 0.0557(16) 0.0336(13) -0.0099(11) -0.0005(12) 0.0176(14) C9 0.0471(19) 0.0348(18) 0.0364(18) -0.0062(14) -0.0044(14) 0.0054(15) C21 0.0506(19) 0.0366(18) 0.0350(17) 0.0000(14) 0.0067(14) 0.0202(15) C20 0.0456(19) 0.0366(18) 0.051(2) 0.0162(15) 0.0060(15) 0.0056(15) C5 0.088(3) 0.0361(19) 0.043(2) 0.0022(16) 0.0138(19) 0.0031(19) C10 0.054(2) 0.043(2) 0.079(3) -0.0059(19) -0.029(2) -0.0040(18) C4 0.080(3) 0.060(3) 0.125(4) 0.028(3) 0.003(3) -0.006(2) C6 0.076(3) 0.046(2) 0.072(3) 0.0086(19) 0.032(2) 0.0097(19) C11 0.160(5) 0.104(4) 0.036(2) -0.004(2) 0.020(3) 0.030(4) _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 P1 O1 1.463(2) . ? P1 O2 1.549(2) . ? P1 O3 1.562(2) . ? P1 C7 1.806(3) . ? O6 C15 1.369(3) . ? C16 C17 1.392(3) . ? C16 C15 1.404(4) . ? C16 C22 1.541(3) . ? N1 C8 1.451(4) . ? N1 C7 1.459(3) . ? C14 C13 1.391(3) . ? C14 C15 1.410(4) . ? C14 C18 1.538(4) . ? C17 C12 1.382(4) . ? O3 C5 1.447(4) . ? C7 C12 1.518(3) . ? C13 C12 1.384(4) . ? O4 C9 1.407(4) . ? O4 C10 1.431(4) . ? O2 C3 1.437(4) . ? C22 C25 1.536(4) . ? C22 C24 1.538(4) . ? C22 C23 1.539(4) . ? C18 C20 1.528(4) . ? C18 C21 1.530(4) . ? C18 C19 1.534(4) . ? C8 C9 1.493(4) . ? C3 C4 1.456(6) . ? O5 C9 1.392(4) . ? O5 C11 1.422(5) . ? C5 C6 1.452(5) . ? 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 O1 P1 O2 117.21(12) . . ? O1 P1 O3 114.58(13) . . ? O2 P1 O3 99.70(12) . . ? O1 P1 C7 110.13(13) . . ? O2 P1 C7 105.36(13) . . ? O3 P1 C7 108.99(12) . . ? C17 C16 C15 117.4(2) . . ? C17 C16 C22 119.6(2) . . ? C15 C16 C22 123.0(2) . . ? C8 N1 C7 113.1(2) . . ? C13 C14 C15 117.2(2) . . ? C13 C14 C18 121.0(2) . . ? C15 C14 C18 121.9(2) . . ? C12 C17 C16 122.3(2) . . ? C5 O3 P1 122.2(2) . . ? N1 C7 C12 111.8(2) . . ? N1 C7 P1 108.48(18) . . ? C12 C7 P1 112.82(18) . . ? C12 C13 C14 122.4(2) . . ? C9 O4 C10 115.1(2) . . ? O6 C15 C16 123.4(2) . . ? O6 C15 C14 114.5(2) . . ? C16 C15 C14 122.0(2) . . ? C17 C12 C13 118.7(2) . . ? C17 C12 C7 120.6(2) . . ? C13 C12 C7 120.6(2) . . ? C3 O2 P1 126.8(2) . . ? C25 C22 C24 106.7(2) . . ? C25 C22 C23 105.8(2) . . ? C24 C22 C23 112.3(2) . . ? C25 C22 C16 111.5(2) . . ? C24 C22 C16 109.5(2) . . ? C23 C22 C16 110.8(2) . . ? C20 C18 C21 107.3(2) . . ? C20 C18 C19 106.8(2) . . ? C21 C18 C19 110.0(2) . . ? C20 C18 C14 111.3(2) . . ? C21 C18 C14 110.8(2) . . ? C19 C18 C14 110.5(2) . . ? N1 C8 C9 110.7(2) . . ? O2 C3 C4 112.0(3) . . ? C9 O5 C11 113.1(3) . . ? O5 C9 O4 112.4(2) . . ? O5 C9 C8 105.9(2) . . ? O4 C9 C8 114.3(3) . . ? O3 C5 C6 112.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.559 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.059