# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/491 #=============================================================================== # Cif file for the paper submitted on Jun the 22nd by Courier mail by # Fernando Lopez-Ortiz # # Synthesis of cyclopentenones and butenolides by reaction of P- # Diphenyl(alkyl)(N-pheny)phophazenes with electrophilic double and triple bonds # Julia M. Álvarez-Gutiérrez,( Fernando López-Ortiz,*Ý Santiago García-Granda,ý # and Alejandra Rodríguez-Gonzálezý # (Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián # Clavería 8, 33071, Oviedo, Spain. # ÝÁrea de Química Orgánica, Universidad de Almería, Carretera de Sacramento, # 04120 Almería, Spain. E-mail: flortiz@ualm.es # ýDepartamento de Química Física y Analítica, Universidad de Oviedo, Julián # Clavería 8, 33071, Oviedo, Spain. # #=============================================================================== data_global #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Santiago Garc\'ia-Granda Departamento de Qu\'imica F\'isica y Anal\'itica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33071 Oviedo Spain ; _publ_contact_author_phone '0034 98 5103477' _publ_contact_author_fax '0034 98 5103125' _publ_contact_author_email sgg@sauron.quimica.uniovi.es _publ_requested_journal 'test' _publ_requested_coeditor_name '' _publ_contact_letter ; Oviedo 05/06/2000 Please receive the CIF for compound "diphenyl[1-(2-phenylamino-3- oxocyclopentyl)ethyl]phosphine oxide",submitted to be published. Thank you very much. S. Garc\'ia-Granda. ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; 'Synthesis of cyclopentenones and butenolides by reaction of P-Diphenyl(alkyl)(N-pheny)phophazenes with electrophilic double and triple bonds' ; loop_ _publ_author_name _publ_author_address 'santiago garc\'ia-granda' ; Departamento de Qu\'imica F\'isica y Anal\'itica Facultad de Qu\'imica Universidad de Oviedo avda. Juli\'an Claver\'ia, 8 33071 Oviedo Spain ; 'alejandra rodr\'iguez-gonz\'alez' ; Departamento de Qu\'imica F\'isica y Anal\'itica Facultad de Qu\'imica Universidad de Oviedo avda. Juli\'an Claver\'ia, 8 33071 Oviedo Spain ; 'julia M. \'alvarez-guti\'errez' ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo avda. Juli\'an Claver\'ia, 8 33071 Oviedo Spain ; 'fernando l\'opez ort\'iz' ; Area de Qu\'imica Org\'anica Universidad de Almer\'ia Crta. De Sacramento, s/n 04120 Almer\'ia Spain ; #============================================================================== # 4. TEXT _publ_section_comment ; On all reflections, profile analysis was performed (Lehman & Larsen, 1974; Grant & Gabe, 1978). Multiple reflections were averaged and Lorentz and polarization corrections were applied. The structure was solved by direct methods using SHELXS97 (Sheldrick, 1997). Isotropic least-squares refinement on F2 using SHELXL97 (Sheldrick, 1997). An empirical absorption correction were applied at this stage, using XABS2 (Parkin et al., 1995). During the final stages of the refinements, all positional parameters and the anisotropic temperature factors of all the non-H atoms were refined. The H-atoms were refined isotropically. Atomic scattering factors were taken from International tables for X-ray Crystallography (1976). Plots were made with the EUCLID package (Spek, 1982). Geometrical calculations were made with PARST (Nardelli, 1983). All calculations were made on the Scientific Computer Centre at the University of Oviedo. ; _publ_section_references ; Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garc\'ia- Granda, S., Gould, R.O., Smits, J.M.M., Smykalla, C., (1992), The DIRDIF program system, Technical Report of the Crystallographic Laboratory, University of Nijmegen, The Netherlands. Grant, D.F. and Gabe, E.J. (1978) J. Appl. Cryst. 11, 114-120. Guti\'errez Rodr\'iguez, A.; Aguirre P\'erez, A.; Garc\'ia-Granda, S. (1998) THE REFLEX V 1.2 E 2 Manual del usuario. Departamento de Qu\'imica F\'isica y Anal\'itica, Universidad de Oviedo. International Tables for X-Ray Crystallography (1974) Vol. IV. Birmingham Kynoch Press. (Present distributor: Kluwer Academic Publishers, Dordrecht) Lehman,M.S. and Larsen,F.K.(1974), Acta Cryst., A30, 580-584. Nardelli, M., (1983), Comput.Chem., 7, 95-98. Sheldrick, G.M. (1997). SHELXL-97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXS-97. Program for the Solution of Crystal Structures. University of G\"ottingen, Germany. Spek, A.L., (1982), The EUCLID package, In 'Computational Crystallography' p. 528, Sayre, D., ed., Clerendon Press, Oxford. Parking S., Moezzi B. and Hope, H.(1995).J.Appl. Cryst. 28, 53-56. ; _publ_section_figure_captions ; Fig. 1 : Euclid (Spek, 1982) plot, showing 30% probability displacement ellipsoids and the atomic numbering scheme. ; _publ_section_acknowledgements ; We thank DGIYT for support (PB96-0556) ; #========================================================================== _audit_creation_method shelxl-97 _chemical_name_systematic ; diphenyl[1-(2-phenylamino-3-oxocyclopentyl)ethyl]phosphine oxide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 N1 O3 P1' _chemical_formula_weight 479.49 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 11.271(1) _cell_length_b 9.216(4) _cell_length_c 24.270(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.27(6) _cell_angle_gamma 90.00 _cell_volume 2519(1) _cell_formula_units_z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 10 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_f_000 1008 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details 'xabs2 (parkin et al., 1995)' _exptl_absorpt_correction_t_min 0.96 _exptl_absorpt_correction_t_max 0.987 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'nonius cad4-diffractometer' _diffrn_measurement_method '\w-2\q scan technique' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 4.34 _diffrn_reflns_number 5192 _diffrn_reflns_av_r_equivalents 0.09 _diffrn_reflns_av_sigmai/neti 0.4066 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.98 _reflns_number_total 4931 _reflns_number_gt 1149 _reflns_threshold_expression >2sigma(i) _computing_data_collection 'CAD-4 Diffractometer Control Software (Emraf-Noniur, 1994)' _computing_cell_refinement 'CRYSDA (Beurskens el al., 1992)' _computing_data_reduction 'REFLEX (local program)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'EUCLID (Spek, 1982)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0331P)^2^+0.0000P] 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 4931 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3456 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.27165(15) 0.18588(19) 0.41298(7) 0.0414(5) Uani 1 d . . . N N 0.5408(5) 0.1470(5) 0.3524(2) 0.0466(15) Uani 1 d . . . H H 0.450(6) 0.129(7) 0.353(2) 0.10(3) Uiso 1 d . . . O1 O 0.5397(3) 0.4779(4) 0.43186(14) 0.0387(11) Uani 1 d . . . O2 O 0.7302(3) 0.5365(5) 0.45007(16) 0.0579(14) Uani 1 d . . . O3 O 0.3062(3) 0.0949(4) 0.36470(15) 0.0481(12) Uani 1 d . . . C2 C 0.6586(6) 0.4576(7) 0.4259(2) 0.0459(18) Uani 1 d . . . C3 C 0.6769(6) 0.3342(7) 0.3917(2) 0.0398(18) Uani 1 d . . . H3 H 0.750(4) 0.301(5) 0.3820(16) 0.021(14) Uiso 1 d . . . C4 C 0.5709(5) 0.2727(7) 0.3784(2) 0.0352(16) Uani 1 d . . . C5 C 0.4728(5) 0.3675(6) 0.4006(2) 0.0306(15) Uani 1 d . . . C6 C 0.3946(4) 0.2924(6) 0.4435(2) 0.0328(15) Uani 1 d . . . H6 H 0.3587 0.3703 0.4647 0.050 Uiso 1 calc . . . C7 C 0.4717(7) 0.2030(9) 0.4847(3) 0.050(2) Uani 1 d . . . H71 H 0.426(3) 0.174(5) 0.5149(16) 0.015(14) Uiso 1 d . . . H72 H 0.548(5) 0.260(6) 0.497(2) 0.06(2) Uiso 1 d . . . H73 H 0.509(5) 0.128(6) 0.466(2) 0.07(2) Uiso 1 d . . . C8 C 0.6232(6) 0.0424(8) 0.3348(2) 0.0459(18) Uani 1 d . . . C9 C 0.7295(7) 0.0776(9) 0.3112(3) 0.060(2) Uani 1 d . . . H9 H 0.748(5) 0.180(6) 0.303(2) 0.06(2) Uiso 1 d . . . C10 C 0.8018(7) -0.0323(12) 0.2937(3) 0.087(3) Uani 1 d . . . H10 H 0.8730 -0.0084 0.2779 0.050 Uiso 1 calc . . . C11 C 0.7724(12) -0.1752(15) 0.2990(4) 0.112(5) Uani 1 d . . . H11 H 0.844(6) -0.223(8) 0.293(3) 0.12(4) Uiso 1 d . . . C12 C 0.6705(12) -0.2106(10) 0.3219(4) 0.094(4) Uani 1 d . . . H12 H 0.640(7) -0.301(8) 0.333(3) 0.12(4) Uiso 1 d . . . C13 C 0.5918(9) -0.1032(10) 0.3406(3) 0.071(3) Uani 1 d . . . H13 H 0.520(5) -0.126(8) 0.352(3) 0.08(3) Uiso 1 d . . . C21 C 0.2152(5) 0.0746(7) 0.4673(3) 0.0433(17) Uani 1 d . . . C22 C 0.1806(6) 0.1264(9) 0.5170(3) 0.057(2) Uani 1 d . . . H22 H 0.174(4) 0.224(5) 0.528(2) 0.036(19) Uiso 1 d . . . C23 C 0.1300(6) 0.0376(10) 0.5558(3) 0.067(2) Uani 1 d . . . H23 H 0.092(5) 0.075(6) 0.596(2) 0.09(2) Uiso 1 d . . . C24 C 0.1161(7) -0.1074(11) 0.5442(4) 0.076(3) Uani 1 d . . . H24 H 0.078(7) -0.175(9) 0.577(3) 0.17(4) Uiso 1 d . . . C25 C 0.1551(8) -0.1626(10) 0.4964(4) 0.080(3) Uani 1 d . . . H25 H 0.158(7) -0.268(9) 0.490(3) 0.15(4) Uiso 1 d . . . C26 C 0.2050(7) -0.0734(9) 0.4570(4) 0.063(2) Uani 1 d . . . H26 H 0.229(5) -0.110(6) 0.424(2) 0.07(3) Uiso 1 d . . . C31 C 0.1516(5) 0.3090(7) 0.3934(3) 0.0390(16) Uani 1 d . . . C32 C 0.1076(6) 0.4104(7) 0.4298(3) 0.0459(18) Uani 1 d . . . H32 H 0.144(5) 0.429(6) 0.468(2) 0.07(2) Uiso 1 d . . . C33 C 0.0106(6) 0.4962(9) 0.4135(4) 0.059(2) Uani 1 d . . . H33 H -0.013(6) 0.565(7) 0.442(3) 0.11(3) Uiso 1 d . . . C34 C -0.0403(7) 0.4783(10) 0.3613(4) 0.072(3) Uani 1 d . . . H34 H -0.105(4) 0.536(5) 0.3462(19) 0.046(18) Uiso 1 d . . . C35 C 0.0017(7) 0.3776(10) 0.3256(3) 0.070(2) Uani 1 d . . . H35 H -0.028(5) 0.361(7) 0.283(2) 0.10(3) Uiso 1 d . . . C36 C 0.0970(7) 0.2940(9) 0.3423(3) 0.059(2) Uani 1 d . . . H36 H 0.129(5) 0.219(6) 0.320(2) 0.06(2) Uiso 1 d . . . C41 C 0.4013(5) 0.4505(7) 0.3560(2) 0.0345(15) Uani 1 d . . . C42 C 0.3374(6) 0.5721(8) 0.3704(3) 0.050(2) Uani 1 d . . . H42 H 0.351(5) 0.601(6) 0.406(2) 0.06(2) Uiso 1 d . . . C43 C 0.2702(7) 0.6478(9) 0.3313(3) 0.069(2) Uani 1 d . . . H43 H 0.224(6) 0.726(7) 0.340(3) 0.09(3) Uiso 1 d . . . C44 C 0.2651(7) 0.6039(8) 0.2778(3) 0.061(2) Uani 1 d . . . H44 H 0.211(5) 0.659(6) 0.245(2) 0.08(2) Uiso 1 d . . . C45 C 0.3274(7) 0.4861(9) 0.2618(3) 0.057(2) Uani 1 d . . . H45 H 0.339(5) 0.462(6) 0.227(2) 0.07(2) Uiso 1 d . . . C46 C 0.3971(6) 0.4109(7) 0.3013(3) 0.0445(19) Uani 1 d . . . H46 H 0.439(4) 0.329(5) 0.2914(17) 0.024(16) Uiso 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 P 0.0416(11) 0.0377(11) 0.0449(11) -0.0025(10) 0.0007(8) -0.0039(10) N 0.044(4) 0.027(4) 0.069(4) -0.013(3) 0.002(3) 0.007(3) O1 0.034(3) 0.032(3) 0.050(3) -0.010(2) 0.002(2) 0.001(2) O2 0.044(3) 0.066(4) 0.065(3) -0.024(3) 0.004(2) -0.008(3) O3 0.048(3) 0.050(3) 0.046(3) -0.016(2) 0.008(2) -0.006(2) C2 0.034(4) 0.058(5) 0.046(4) -0.002(4) 0.003(3) -0.007(4) C3 0.038(5) 0.038(5) 0.044(4) -0.014(3) 0.004(3) 0.016(4) C4 0.033(4) 0.040(5) 0.032(4) 0.002(3) -0.002(3) 0.006(4) C5 0.029(3) 0.023(4) 0.040(4) -0.009(3) 0.001(3) 0.004(3) C6 0.035(4) 0.029(4) 0.034(4) -0.001(3) -0.006(3) -0.002(3) C7 0.049(5) 0.060(6) 0.039(5) 0.015(5) -0.001(4) 0.001(5) C8 0.065(5) 0.030(5) 0.042(4) 0.000(4) -0.004(4) 0.020(4) C9 0.086(6) 0.044(6) 0.053(5) -0.005(4) 0.019(4) 0.025(5) C10 0.081(6) 0.112(8) 0.069(6) -0.011(7) 0.009(4) 0.051(7) C11 0.139(12) 0.128(12) 0.068(7) -0.003(8) 0.000(7) 0.091(12) C12 0.177(12) 0.032(6) 0.071(7) -0.005(6) 0.008(7) 0.036(8) C13 0.107(8) 0.048(6) 0.059(6) -0.011(5) 0.002(5) 0.012(6) C21 0.044(4) 0.039(5) 0.047(4) 0.008(4) -0.002(3) -0.005(4) C22 0.069(5) 0.043(5) 0.060(6) -0.001(5) 0.005(4) -0.013(5) C23 0.070(5) 0.072(7) 0.058(6) 0.031(6) 0.008(4) -0.010(5) C24 0.054(5) 0.092(8) 0.080(7) 0.051(7) -0.017(5) -0.020(6) C25 0.093(7) 0.043(7) 0.101(8) 0.036(7) -0.016(6) -0.019(5) C26 0.077(6) 0.036(5) 0.076(7) 0.002(5) -0.001(5) -0.005(5) C31 0.031(4) 0.038(4) 0.047(4) 0.011(4) -0.004(3) -0.004(4) C32 0.039(4) 0.052(5) 0.046(5) 0.004(4) 0.001(4) 0.002(4) C33 0.042(5) 0.052(6) 0.082(7) 0.013(5) 0.010(5) 0.007(4) C34 0.040(5) 0.080(7) 0.096(8) 0.043(6) -0.006(5) 0.003(5) C35 0.043(5) 0.096(7) 0.070(7) 0.005(6) -0.014(5) -0.015(5) C36 0.042(5) 0.077(6) 0.057(6) 0.007(5) -0.002(4) 0.000(5) C41 0.037(4) 0.028(4) 0.039(4) -0.004(3) 0.002(3) -0.006(3) C42 0.065(5) 0.040(5) 0.046(5) -0.006(4) -0.006(4) 0.012(4) C43 0.087(6) 0.059(6) 0.061(6) 0.015(5) 0.006(5) 0.032(5) C44 0.083(6) 0.049(5) 0.050(5) 0.010(4) -0.004(5) 0.014(5) C45 0.079(6) 0.054(6) 0.037(5) 0.008(5) 0.001(4) 0.000(4) C46 0.059(5) 0.030(5) 0.043(5) -0.007(4) -0.005(4) 0.005(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 P O3 1.504(4) . yes P C21 1.806(6) . yes P C31 1.815(6) . yes P C6 1.831(5) . yes N C4 1.356(7) . yes N C8 1.416(7) . yes N H 1.04(6) . yes O1 C2 1.366(6) . yes O1 C5 1.462(6) . yes O2 C2 1.220(6) . yes C2 C3 1.428(8) . yes C3 C4 1.350(8) . yes C3 H3 0.92(4) . yes C4 C5 1.524(7) . yes C5 C41 1.529(7) . yes C5 C6 1.553(7) . yes C6 C7 1.539(8) . yes C6 H6 0.9800 . yes C7 H71 0.95(4) . yes C7 H72 1.05(5) . yes C7 H73 0.94(5) . yes C8 C9 1.387(8) . yes C8 C13 1.396(10) . yes C9 C10 1.378(9) . yes C9 H9 0.99(5) . yes C10 C11 1.365(14) . yes C10 H10 0.9300 . yes C11 C12 1.336(14) . yes C11 H11 0.93(7) . yes C12 C13 1.415(12) . yes C12 H12 0.95(7) . yes C13 H13 0.89(6) . yes C21 C22 1.369(8) . yes C21 C26 1.391(8) . yes C22 C23 1.386(9) . yes C22 H22 0.94(5) . yes C23 C24 1.373(10) . yes C23 H23 1.14(6) . yes C24 C25 1.354(11) . yes C24 H24 1.12(8) . yes C25 C26 1.397(10) . yes C25 H25 0.98(8) . yes C26 H26 0.91(5) . yes C31 C36 1.371(8) . yes C31 C32 1.391(8) . yes C32 C33 1.394(8) . yes C32 H32 1.01(5) . yes C33 C34 1.381(10) . yes C33 H33 0.98(6) . yes C34 C35 1.367(10) . yes C34 H34 0.97(5) . yes C35 C36 1.370(9) . yes C35 H35 1.08(6) . yes C36 H36 0.95(5) . yes C41 C46 1.376(7) . yes C41 C42 1.385(8) . yes C42 C43 1.382(9) . yes C42 H42 0.90(5) . yes C43 C44 1.358(9) . yes C43 H43 0.92(6) . yes C44 C45 1.358(9) . yes C44 H44 1.11(5) . yes C45 C46 1.398(8) . yes C45 H45 0.88(5) . yes C46 H46 0.93(4) . yes 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 O3 P C21 111.2(3) . . yes O3 P C31 111.0(3) . . yes C21 P C31 105.4(3) . . yes O3 P C6 113.5(2) . . yes C21 P C6 107.0(3) . . yes C31 P C6 108.4(3) . . yes C4 N C8 124.5(6) . . yes C4 N H 111(3) . . yes C8 N H 124(3) . . yes C2 O1 C5 109.7(4) . . yes O2 C2 O1 120.0(6) . . yes O2 C2 C3 130.3(6) . . yes O1 C2 C3 109.7(6) . . yes C4 C3 C2 109.0(6) . . yes C4 C3 H3 126(3) . . yes C2 C3 H3 125(3) . . yes C3 C4 N 132.3(6) . . yes C3 C4 C5 108.9(5) . . yes N C4 C5 118.8(5) . . yes O1 C5 C4 102.5(4) . . yes O1 C5 C41 105.4(4) . . yes C4 C5 C41 114.0(5) . . yes O1 C5 C6 104.9(4) . . yes C4 C5 C6 114.8(5) . . yes C41 C5 C6 113.6(5) . . yes C7 C6 C5 110.7(5) . . yes C7 C6 P 112.0(5) . . yes C5 C6 P 114.1(4) . . yes C7 C6 H6 106.5 . . yes C5 C6 H6 106.5 . . yes P C6 H6 106.5 . . yes C6 C7 H71 110(3) . . yes C6 C7 H72 111(3) . . yes H71 C7 H72 113(4) . . yes C6 C7 H73 110(4) . . yes H71 C7 H73 116(5) . . yes H72 C7 H73 97(5) . . yes C9 C8 C13 119.5(7) . . yes C9 C8 N 123.6(7) . . yes C13 C8 N 116.9(7) . . yes C10 C9 C8 119.1(8) . . yes C10 C9 H9 120(3) . . yes C8 C9 H9 120(3) . . yes C11 C10 C9 122.1(10) . . yes C11 C10 H10 118.9 . . yes C9 C10 H10 118.9 . . yes C12 C11 C10 119.4(11) . . yes C12 C11 H11 135(5) . . yes C10 C11 H11 103(5) . . yes C11 C12 C13 121.5(11) . . yes C11 C12 H12 132(5) . . yes C13 C12 H12 106(5) . . yes C8 C13 C12 118.4(10) . . yes C8 C13 H13 120(5) . . yes C12 C13 H13 122(5) . . yes C22 C21 C26 118.5(7) . . yes C22 C21 P 124.5(6) . . yes C26 C21 P 117.0(6) . . yes C21 C22 C23 122.1(8) . . yes C21 C22 H22 127(3) . . yes C23 C22 H22 110(3) . . yes C24 C23 C22 118.8(9) . . yes C24 C23 H23 115(3) . . yes C22 C23 H23 126(3) . . yes C25 C24 C23 120.2(9) . . yes C25 C24 H24 124(4) . . yes C23 C24 H24 116(4) . . yes C24 C25 C26 121.2(9) . . yes C24 C25 H25 121(5) . . yes C26 C25 H25 117(5) . . yes C21 C26 C25 119.1(9) . . yes C21 C26 H26 120(4) . . yes C25 C26 H26 121(4) . . yes C36 C31 C32 119.0(7) . . yes C36 C31 P 118.5(6) . . yes C32 C31 P 122.3(5) . . yes C31 C32 C33 119.8(7) . . yes C31 C32 H32 123(3) . . yes C33 C32 H32 117(3) . . yes C34 C33 C32 119.0(8) . . yes C34 C33 H33 127(4) . . yes C32 C33 H33 114(4) . . yes C35 C34 C33 121.4(8) . . yes C35 C34 H34 114(3) . . yes C33 C34 H34 124(3) . . yes C34 C35 C36 118.8(8) . . yes C34 C35 H35 126(3) . . yes C36 C35 H35 115(3) . . yes C35 C36 C31 122.0(8) . . yes C35 C36 H36 124(4) . . yes C31 C36 H36 114(4) . . yes C46 C41 C42 117.5(6) . . yes C46 C41 C5 123.2(6) . . yes C42 C41 C5 119.4(6) . . yes C43 C42 C41 120.7(7) . . yes C43 C42 H42 125(4) . . yes C41 C42 H42 114(4) . . yes C44 C43 C42 120.6(8) . . yes C44 C43 H43 117(4) . . yes C42 C43 H43 122(4) . . yes C43 C44 C45 120.6(7) . . yes C43 C44 H44 123(3) . . yes C45 C44 H44 116(3) . . yes C44 C45 C46 118.9(7) . . yes C44 C45 H45 125(4) . . yes C46 C45 H45 115(4) . . yes C41 C46 C45 121.8(7) . . yes C41 C46 H46 118(3) . . yes C45 C46 H46 120(3) . . yes 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 C5 O1 C2 O2 -178.0(5) . . . . yes C5 O1 C2 C3 -0.8(6) . . . . yes O2 C2 C3 C4 173.8(6) . . . . yes O1 C2 C3 C4 -3.1(7) . . . . yes C2 C3 C4 N -171.9(6) . . . . yes C2 C3 C4 C5 5.4(7) . . . . yes C8 N C4 C3 3.6(10) . . . . yes C8 N C4 C5 -173.5(5) . . . . yes C2 O1 C5 C4 3.7(6) . . . . yes C2 O1 C5 C41 -115.8(5) . . . . yes C2 O1 C5 C6 124.0(5) . . . . yes C3 C4 C5 O1 -5.6(6) . . . . yes N C4 C5 O1 172.1(5) . . . . yes C3 C4 C5 C41 107.7(6) . . . . yes N C4 C5 C41 -74.5(7) . . . . yes C3 C4 C5 C6 -118.7(6) . . . . yes N C4 C5 C6 59.0(7) . . . . yes O1 C5 C6 C7 -69.1(6) . . . . yes C4 C5 C6 C7 42.5(7) . . . . yes C41 C5 C6 C7 176.3(5) . . . . yes O1 C5 C6 P 163.4(3) . . . . yes C4 C5 C6 P -84.9(5) . . . . yes C41 C5 C6 P 48.8(6) . . . . yes O3 P C6 C7 -83.4(5) . . . . yes C21 P C6 C7 39.6(5) . . . . yes C31 P C6 C7 152.9(5) . . . . yes O3 P C6 C5 43.4(5) . . . . yes C21 P C6 C5 166.5(4) . . . . yes C31 P C6 C5 -80.3(5) . . . . yes C4 N C8 C9 -40.0(9) . . . . yes C4 N C8 C13 141.8(7) . . . . yes C13 C8 C9 C10 0.3(11) . . . . yes N C8 C9 C10 -177.9(6) . . . . yes C8 C9 C10 C11 -0.1(13) . . . . yes C9 C10 C11 C12 -0.2(16) . . . . yes C10 C11 C12 C13 0.4(17) . . . . yes C9 C8 C13 C12 -0.1(11) . . . . yes N C8 C13 C12 178.2(7) . . . . yes C11 C12 C13 C8 -0.2(14) . . . . yes O3 P C21 C22 177.8(5) . . . . yes C31 P C21 C22 -61.9(7) . . . . yes C6 P C21 C22 53.3(6) . . . . yes O3 P C21 C26 -3.4(6) . . . . yes C31 P C21 C26 117.0(6) . . . . yes C6 P C21 C26 -127.8(5) . . . . yes C26 C21 C22 C23 -3.5(11) . . . . yes P C21 C22 C23 175.3(5) . . . . yes C21 C22 C23 C24 1.1(12) . . . . yes C22 C23 C24 C25 2.2(13) . . . . yes C23 C24 C25 C26 -3.0(14) . . . . yes C22 C21 C26 C25 2.7(11) . . . . yes P C21 C26 C25 -176.2(6) . . . . yes C24 C25 C26 C21 0.5(13) . . . . yes O3 P C31 C36 8.4(6) . . . . yes C21 P C31 C36 -112.1(6) . . . . yes C6 P C31 C36 133.7(5) . . . . yes O3 P C31 C32 -176.5(5) . . . . yes C21 P C31 C32 63.0(6) . . . . yes C6 P C31 C32 -51.2(6) . . . . yes C36 C31 C32 C33 -1.1(10) . . . . yes P C31 C32 C33 -176.2(5) . . . . yes C31 C32 C33 C34 0.2(10) . . . . yes C32 C33 C34 C35 0.5(11) . . . . yes C33 C34 C35 C36 -0.4(12) . . . . yes C34 C35 C36 C31 -0.5(12) . . . . yes C32 C31 C36 C35 1.2(11) . . . . yes P C31 C36 C35 176.5(6) . . . . yes O1 C5 C41 C46 131.9(5) . . . . yes C4 C5 C41 C46 20.2(8) . . . . yes C6 C5 C41 C46 -113.9(6) . . . . yes O1 C5 C41 C42 -47.9(7) . . . . yes C4 C5 C41 C42 -159.5(5) . . . . yes C6 C5 C41 C42 66.4(7) . . . . yes C46 C41 C42 C43 1.5(10) . . . . yes C5 C41 C42 C43 -178.8(6) . . . . yes C41 C42 C43 C44 0.3(11) . . . . yes C42 C43 C44 C45 -1.0(12) . . . . yes C43 C44 C45 C46 -0.1(11) . . . . yes C42 C41 C46 C45 -2.6(9) . . . . yes C5 C41 C46 C45 177.7(6) . . . . yes C44 C45 C46 C41 1.9(11) . . . . yes loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm # - - - --- ----- ----- ------- ---- N H O(3) 1.04(6) 1.69(7) 2.716(7) 171.(6) 1_555 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.279 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.065