# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 ---------- X-Sun-Data-Type: ciffile X-Sun-Data-Name: 164809-10 X-Sun-Charset: us-ascii X-Sun-Content-Lines: 1208 data_global # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author 'Jacques ANDRIEU' _publ_contact_author_email jacques.andrieu@u-bourgogne.fr #------------------------------------------------------------------------- loop_ _publ_author_name 'Andrieu, J.' 'Camus, J-M.' 'Poli, R.' 'Richard, R.' _journal_name_full 'New Journal of Chemistry' _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _ccdc_journal_depnumber ? _ccdc_temp_data_collection 110(2) data_p31 _database_code_CSD 164809 _audit_creation_date 2000-10-19T15:55:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C54 H52 N2 P2 S2' _chemical_formula_weight 855.04 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0532(4) _cell_length_b 18.5975(9) _cell_length_c 13.4262(8) _cell_angle_alpha 90 _cell_angle_beta 92.218(2) _cell_angle_gamma 90 _cell_volume 2258.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.228 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 14691 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_unetI/netI 0.0828 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 9440 _reflns_number_gt 7329 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0311P)^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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0028(5) _refine_ls_number_reflns 9440 _refine_ls_number_parameters 549 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_diff_density_max 0.271 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S S -0.14698(7) -0.23346(4) -0.63855(4) 0.02524(16) Uani 1 1 d . . . P P -0.16367(7) -0.26110(4) -0.77980(4) 0.01982(15) Uani 1 1 d . . . N N 0.1146(2) -0.30106(12) -0.77364(14) 0.0214(5) Uani 1 1 d . . . H1N H 0.119(3) -0.2772(13) -0.7129(16) 0.026 Uiso 1 1 d . . . C1 C 0.0167(2) -0.25933(13) -0.84087(16) 0.0190(5) Uani 1 1 d . . . H1 H 0.0043 -0.2869 -0.9028 0.023 Uiso 1 1 calc R . . C2 C 0.2666(2) -0.30923(14) -0.80678(17) 0.0247(6) Uani 1 1 d . . . H2 H 0.3098 -0.2615 -0.8163 0.03 Uiso 1 1 calc R . . C3 C 0.3542(3) -0.34831(16) -0.72483(18) 0.0323(7) Uani 1 1 d . . . H3B H 0.3509 -0.3213 -0.664 0.048 Uiso 1 1 calc R . . H3A H 0.455 -0.3533 -0.7434 0.048 Uiso 1 1 calc R . . H3C H 0.3121 -0.3951 -0.7151 0.048 Uiso 1 1 calc R . . C4 C 0.0645(2) -0.18400(14) -0.86950(17) 0.0197(6) Uani 1 1 d . . . C5 C 0.0906(3) -0.13062(15) -0.79824(18) 0.0254(6) Uani 1 1 d . . . H5 H 0.0835 -0.1415 -0.731 0.03 Uiso 1 1 calc R . . C6 C 0.1271(3) -0.06137(15) -0.8268(2) 0.0296(7) Uani 1 1 d . . . H6 H 0.1436 -0.026 -0.7787 0.036 Uiso 1 1 calc R . . C7 C 0.1390(3) -0.04458(15) -0.9263(2) 0.0319(7) Uani 1 1 d . . . H7 H 0.162 0.002 -0.9454 0.038 Uiso 1 1 calc R . . C8 C 0.1164(3) -0.09790(15) -0.9976(2) 0.0288(7) Uani 1 1 d . . . H8 H 0.1253 -0.0871 -1.0647 0.035 Uiso 1 1 calc R . . C9 C 0.0805(3) -0.16714(15) -0.96910(18) 0.0244(6) Uani 1 1 d . . . H9 H 0.067 -0.2027 -1.0173 0.029 Uiso 1 1 calc R . . C10 C 0.2691(2) -0.35077(14) -0.90428(17) 0.0213(6) Uani 1 1 d . . . C11 C 0.3508(3) -0.32607(15) -0.98231(18) 0.0300(7) Uani 1 1 d . . . H11 H 0.3977 -0.2816 -0.9773 0.036 Uiso 1 1 calc R . . C12 C 0.3634(3) -0.36727(17) -1.06860(19) 0.0372(8) Uani 1 1 d . . . H12 H 0.4179 -0.35 -1.1208 0.045 Uiso 1 1 calc R . . C13 C 0.2956(3) -0.43301(17) -1.07644(19) 0.0362(8) Uani 1 1 d . . . H13 H 0.3068 -0.4612 -1.1329 0.043 Uiso 1 1 calc R . . C14 C 0.2103(3) -0.45736(16) -0.99986(19) 0.0346(7) Uani 1 1 d . . . H14 H 0.1621 -0.5014 -1.0056 0.042 Uiso 1 1 calc R . . C15 C 0.1968(3) -0.41605(14) -0.91455(18) 0.0253(6) Uani 1 1 d . . . H15 H 0.1385 -0.4324 -0.8638 0.03 Uiso 1 1 calc R . . C16 C -0.2327(2) -0.35236(13) -0.79831(17) 0.0208(6) Uani 1 1 d . . . C17 C -0.2993(3) -0.37491(15) -0.88820(19) 0.0278(6) Uani 1 1 d . . . H17 H -0.3025 -0.3438 -0.9425 0.033 Uiso 1 1 calc R . . C18 C -0.3608(3) -0.44260(15) -0.8981(2) 0.0292(7) Uani 1 1 d . . . H18 H -0.407 -0.4565 -0.9581 0.035 Uiso 1 1 calc R . . C20 C -0.2845(3) -0.46922(16) -0.7297(2) 0.0365(7) Uani 1 1 d . . . H20 H -0.2787 -0.5013 -0.6766 0.044 Uiso 1 1 calc R . . C19 C -0.3532(3) -0.48936(15) -0.8188(2) 0.0339(7) Uani 1 1 d . . . H19 H -0.3947 -0.5349 -0.8253 0.041 Uiso 1 1 calc R . . C21 C -0.2237(3) -0.40064(15) -0.71950(19) 0.0310(7) Uani 1 1 d . . . H21 H -0.1769 -0.3871 -0.6595 0.037 Uiso 1 1 calc R . . C22 C -0.2882(2) -0.20383(13) -0.85264(17) 0.0197(6) Uani 1 1 d . . . C23 C -0.2901(3) -0.20301(14) -0.95694(18) 0.0240(6) Uani 1 1 d . . . H23 H -0.2226 -0.2305 -0.9909 0.029 Uiso 1 1 calc R . . C24 C -0.3926(3) -0.16128(15) -1.00934(19) 0.0273(6) Uani 1 1 d . . . H24 H -0.395 -0.1615 -1.0787 0.033 Uiso 1 1 calc R . . C25 C -0.4910(3) -0.11946(15) -0.95982(19) 0.0312(7) Uani 1 1 d . . . H25 H -0.5594 -0.0914 -0.9957 0.037 Uiso 1 1 calc R . . C26 C -0.4888(3) -0.11893(15) -0.8571(2) 0.0318(7) Uani 1 1 d . . . H26 H -0.5556 -0.0905 -0.8239 0.038 Uiso 1 1 calc R . . C27 C -0.3873(3) -0.16060(14) -0.80322(18) 0.0238(6) Uani 1 1 d . . . H27 H -0.3853 -0.1597 -0.7339 0.029 Uiso 1 1 calc R . . S# S -0.08297(7) -0.33648(4) -0.13927(5) 0.02852(17) Uani 1 1 d . . . P# P -0.12919(7) -0.30871(4) -0.27815(5) 0.02191(16) Uani 1 1 d . . . N# N 0.1718(2) -0.29098(12) -0.30026(15) 0.0272(6) Uani 1 1 d . . . H2N H 0.164(3) -0.3050(16) -0.2449(18) 0.033 Uiso 1 1 d . . . C1# C 0.0402(3) -0.31483(14) -0.35600(17) 0.0227(6) Uani 1 1 d . . . H1# H 0.0251 -0.2829 -0.4135 0.027 Uiso 1 1 calc R . . C2# C 0.2050(3) -0.21379(14) -0.29977(17) 0.0263(6) Uani 1 1 d . . . H2# H 0.1178 -0.1866 -0.2805 0.032 Uiso 1 1 calc R . . C3# C 0.3325(3) -0.20164(16) -0.22302(19) 0.0389(8) Uani 1 1 d . . . H3A# H 0.3022 -0.216 -0.1582 0.058 Uiso 1 1 calc R . . H3B# H 0.3588 -0.1516 -0.2219 0.058 Uiso 1 1 calc R . . H3C# H 0.4164 -0.2297 -0.241 0.058 Uiso 1 1 calc R . . C4# C 0.0630(3) -0.39066(14) -0.39502(18) 0.0212(6) Uani 1 1 d . . . C5# C 0.0918(3) -0.44732(15) -0.32987(19) 0.0269(6) Uani 1 1 d . . . H5# H 0.0925 -0.4395 -0.2614 0.032 Uiso 1 1 calc R . . C6# C 0.1196(3) -0.51571(15) -0.3664(2) 0.0294(7) Uani 1 1 d . . . H6# H 0.1401 -0.5534 -0.3226 0.035 Uiso 1 1 calc R . . C7# C 0.1167(3) -0.52748(15) -0.4676(2) 0.0323(7) Uani 1 1 d . . . H7# H 0.1342 -0.5734 -0.492 0.039 Uiso 1 1 calc R . . C8# C 0.0879(3) -0.47156(16) -0.5331(2) 0.0310(7) Uani 1 1 d . . . H8# H 0.0863 -0.4797 -0.6014 0.037 Uiso 1 1 calc R . . C9# C 0.0614(3) -0.40301(15) -0.49649(19) 0.0280(6) Uani 1 1 d . . . H9# H 0.0424 -0.3653 -0.5406 0.034 Uiso 1 1 calc R . . C10# C 0.2518(3) -0.18950(14) -0.40306(17) 0.0234(6) Uani 1 1 d . . . C11# C 0.3530(3) -0.22816(16) -0.45548(18) 0.0292(6) Uani 1 1 d . . . H11# H 0.3864 -0.2724 -0.4314 0.035 Uiso 1 1 calc R . . C12# C 0.4051(3) -0.20142(16) -0.5441(2) 0.0338(7) Uani 1 1 d . . . H12# H 0.4743 -0.2273 -0.5789 0.041 Uiso 1 1 calc R . . C13# C 0.3537(3) -0.13594(18) -0.58027(19) 0.0391(8) Uani 1 1 d . . . H13# H 0.3902 -0.1173 -0.6387 0.047 Uiso 1 1 calc R . . C14# C 0.2488(3) -0.09846(17) -0.53026(19) 0.0372(7) Uani 1 1 d . . . H14# H 0.2121 -0.0552 -0.5555 0.045 Uiso 1 1 calc R . . C15# C 0.1983(3) -0.12596(16) -0.44142(18) 0.0294(6) Uani 1 1 d . . . H15# H 0.1271 -0.1008 -0.4075 0.035 Uiso 1 1 calc R . . C16# C -0.1949(3) -0.21553(14) -0.28744(18) 0.0232(6) Uani 1 1 d . . . C17# C -0.2888(3) -0.19207(16) -0.3654(2) 0.0348(7) Uani 1 1 d . . . H17# H -0.317 -0.2236 -0.4165 0.042 Uiso 1 1 calc R . . C18# C -0.3403(3) -0.12202(16) -0.3671(2) 0.0390(7) Uani 1 1 d . . . H18# H -0.4034 -0.1067 -0.4191 0.047 Uiso 1 1 calc R . . C19# C -0.2987(3) -0.07475(15) -0.2920(2) 0.0368(8) Uani 1 1 d . . . H19# H -0.3351 -0.028 -0.2927 0.044 Uiso 1 1 calc R . . C20# C -0.2029(4) -0.09720(16) -0.2159(2) 0.0444(8) Uani 1 1 d . . . H20# H -0.1719 -0.065 -0.1663 0.053 Uiso 1 1 calc R . . C21# C -0.1531(3) -0.16714(15) -0.21324(18) 0.0342(7) Uani 1 1 d . . . H21# H -0.0904 -0.1821 -0.1608 0.041 Uiso 1 1 calc R . . C22# C -0.2740(2) -0.36273(13) -0.33847(17) 0.0188(6) Uani 1 1 d . . . C23# C -0.2990(3) -0.36163(14) -0.44181(17) 0.0241(6) Uani 1 1 d . . . H23# H -0.2364 -0.3356 -0.4816 0.029 Uiso 1 1 calc R . . C24# C -0.4157(3) -0.39889(15) -0.48477(19) 0.0299(7) Uani 1 1 d . . . H24# H -0.4324 -0.3974 -0.5535 0.036 Uiso 1 1 calc R . . C25# C -0.5089(3) -0.43864(15) -0.4267(2) 0.0339(7) Uani 1 1 d . . . H25# H -0.5882 -0.4636 -0.4561 0.041 Uiso 1 1 calc R . . C26# C -0.4832(3) -0.44098(16) -0.3247(2) 0.0347(7) Uani 1 1 d . . . H26# H -0.5446 -0.4683 -0.2856 0.042 Uiso 1 1 calc R . . C27# C -0.3673(3) -0.40326(14) -0.28047(19) 0.0266(6) Uani 1 1 d . . . H27# H -0.3514 -0.4049 -0.2117 0.032 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 S 0.0292(4) 0.0274(4) 0.0193(3) -0.0007(3) 0.0034(3) 0.0005(3) P 0.0184(3) 0.0212(4) 0.0200(3) 0.0004(3) 0.0021(3) 0.0018(3) N 0.0181(11) 0.0256(12) 0.0207(11) -0.0011(10) 0.0010(9) 0.0044(10) C1 0.0162(12) 0.0206(14) 0.0202(13) 0.0004(11) 0.0003(10) 0.0035(11) C2 0.0183(13) 0.0217(14) 0.0341(15) -0.0003(13) 0.0026(11) 0.0022(12) C3 0.0243(14) 0.0379(18) 0.0343(15) -0.0037(14) -0.0038(11) 0.0095(13) C4 0.0116(12) 0.0236(15) 0.0239(14) 0.0026(12) 0.0012(10) 0.0019(11) C5 0.0192(14) 0.0312(17) 0.0260(14) 0.0003(13) 0.0036(11) 0.0011(12) C6 0.0229(15) 0.0248(16) 0.0415(17) -0.0084(13) 0.0071(12) -0.0005(12) C7 0.0229(16) 0.0183(16) 0.055(2) 0.0078(15) 0.0122(13) 0.0008(12) C8 0.0204(14) 0.0341(18) 0.0320(15) 0.0118(14) 0.0042(11) 0.0027(12) C9 0.0211(14) 0.0226(16) 0.0295(15) -0.0009(12) -0.0004(11) -0.0011(11) C10 0.0135(12) 0.0220(15) 0.0284(14) 0.0027(12) -0.0004(10) 0.0060(11) C11 0.0252(15) 0.0257(17) 0.0395(16) 0.0100(13) 0.0055(12) 0.0065(12) C12 0.0336(16) 0.051(2) 0.0280(16) 0.0096(14) 0.0115(12) 0.0142(15) C13 0.0422(19) 0.041(2) 0.0250(16) -0.0043(14) -0.0054(13) 0.0163(16) C14 0.0342(17) 0.0300(18) 0.0391(17) -0.0037(14) -0.0072(13) 0.0017(13) C15 0.0228(14) 0.0266(17) 0.0266(15) 0.0046(13) 0.0014(11) -0.0021(12) C16 0.0170(13) 0.0201(15) 0.0256(14) 0.0049(12) 0.0062(11) 0.0027(11) C17 0.0305(15) 0.0251(17) 0.0280(15) 0.0043(12) 0.0031(12) 0.0014(12) C18 0.0324(17) 0.0234(17) 0.0318(15) -0.0036(13) 0.0012(12) -0.0002(13) C20 0.053(2) 0.0237(18) 0.0324(17) 0.0105(13) 0.0019(14) 0.0002(15) C19 0.0406(17) 0.0174(16) 0.0440(18) -0.0006(14) 0.0064(14) -0.0038(13) C21 0.0340(16) 0.0296(18) 0.0290(15) 0.0026(13) -0.0044(12) -0.0018(13) C22 0.0148(12) 0.0195(15) 0.0251(14) 0.0032(11) 0.0023(10) -0.0027(10) C23 0.0188(13) 0.0244(16) 0.0291(15) 0.0024(12) 0.0038(11) 0.0009(11) C24 0.0244(14) 0.0298(17) 0.0277(14) 0.0094(13) 0.0002(11) -0.0036(13) C25 0.0189(14) 0.0313(17) 0.0432(18) 0.0123(14) -0.0023(12) 0.0027(12) C26 0.0234(15) 0.0260(17) 0.0465(17) 0.0020(14) 0.0084(12) 0.0063(12) C27 0.0218(14) 0.0260(16) 0.0238(14) 0.0022(12) 0.0028(11) 0.0025(12) S# 0.0359(4) 0.0300(4) 0.0197(3) 0.0015(3) 0.0006(3) 0.0036(3) P# 0.0225(4) 0.0227(4) 0.0206(3) 0.0008(3) 0.0023(3) -0.0004(3) N# 0.0289(13) 0.0272(14) 0.0252(12) 0.0045(11) -0.0034(11) -0.0050(10) C1# 0.0227(13) 0.0237(16) 0.0215(13) 0.0029(12) -0.0013(10) -0.0012(11) C2# 0.0251(14) 0.0254(16) 0.0285(15) -0.0013(12) 0.0019(11) -0.0024(12) C3# 0.0494(19) 0.0357(19) 0.0310(16) -0.0005(13) -0.0063(13) -0.0157(15) C4# 0.0145(13) 0.0215(15) 0.0276(14) 0.0022(12) 0.0016(10) -0.0007(11) C5# 0.0230(15) 0.0287(17) 0.0293(14) -0.0037(13) 0.0057(11) -0.0026(12) C6# 0.0227(15) 0.0234(16) 0.0424(17) 0.0014(13) 0.0064(12) -0.0004(12) C7# 0.0231(15) 0.0244(16) 0.0498(18) -0.0124(15) 0.0053(13) -0.0015(12) C8# 0.0248(15) 0.0355(19) 0.0329(16) -0.0116(14) 0.0041(12) -0.0011(13) C9# 0.0221(14) 0.0305(17) 0.0314(15) -0.0016(13) 0.0014(11) -0.0028(12) C10# 0.0183(13) 0.0259(16) 0.0257(14) -0.0026(12) -0.0030(11) -0.0052(11) C11# 0.0285(15) 0.0244(16) 0.0347(16) -0.0006(13) 0.0026(12) -0.0014(13) C12# 0.0262(15) 0.0369(19) 0.0388(17) -0.0103(14) 0.0082(12) 0.0004(13) C13# 0.0334(17) 0.056(2) 0.0280(16) 0.0080(15) 0.0021(13) -0.0044(16) C14# 0.0338(17) 0.0379(19) 0.0394(17) 0.0114(14) -0.0045(13) 0.0029(14) C15# 0.0254(15) 0.0318(17) 0.0309(15) -0.0040(14) 0.0009(12) 0.0006(13) C16# 0.0247(14) 0.0228(16) 0.0228(14) 0.0010(12) 0.0066(11) 0.0009(11) C17# 0.0324(16) 0.0246(18) 0.0468(18) 0.0010(14) -0.0058(14) -0.0010(13) C18# 0.0290(17) 0.0239(18) 0.063(2) 0.0153(16) -0.0059(14) 0.0018(14) C19# 0.0389(18) 0.0189(17) 0.054(2) 0.0057(15) 0.0223(15) 0.0027(14) C20# 0.075(2) 0.0234(18) 0.0366(18) -0.0039(14) 0.0196(17) -0.0010(17) C21# 0.0558(19) 0.0296(18) 0.0173(14) -0.0011(13) 0.0046(13) 0.0040(15) C22# 0.0176(13) 0.0175(14) 0.0215(13) 0.0008(11) 0.0021(10) 0.0045(10) C23# 0.0222(14) 0.0229(16) 0.0275(15) 0.0029(12) 0.0058(11) 0.0009(12) C24# 0.0271(15) 0.0373(18) 0.0247(14) 0.0005(13) -0.0053(12) 0.0040(13) C25# 0.0224(15) 0.0352(19) 0.0442(18) -0.0052(14) 0.0011(13) -0.0080(13) C26# 0.0234(15) 0.0401(19) 0.0410(17) 0.0011(15) 0.0078(13) -0.0103(14) C27# 0.0245(15) 0.0271(16) 0.0284(14) 0.0031(12) 0.0049(11) 0.0021(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S P 1.9651(8) . ? P C22 1.810(3) . ? P C16 1.822(3) . ? P C1 1.856(2) . ? N C1 1.463(3) . ? N C2 1.471(3) . ? N H1N 0.93(2) . ? C1 C4 1.520(3) . ? C1 H1 0.98 . ? C2 C3 1.516(3) . ? C2 C10 1.521(3) . ? C2 H2 0.98 . ? C3 H3B 0.96 . ? C3 H3A 0.96 . ? C3 H3C 0.96 . ? C4 C9 1.386(3) . ? C4 C5 1.393(3) . ? C5 C6 1.387(4) . ? C5 H5 0.93 . ? C6 C7 1.380(3) . ? C6 H6 0.93 . ? C7 C8 1.388(4) . ? C7 H7 0.93 . ? C8 C9 1.386(4) . ? C8 H8 0.93 . ? C9 H9 0.93 . ? C10 C15 1.384(3) . ? C10 C11 1.384(3) . ? C11 C12 1.397(4) . ? C11 H11 0.93 . ? C12 C13 1.370(4) . ? C12 H12 0.93 . ? C13 C14 1.385(4) . ? C13 H13 0.93 . ? C14 C15 1.389(3) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C16 C21 1.388(3) . ? C16 C17 1.393(3) . ? C17 C18 1.381(4) . ? C17 H17 0.93 . ? C18 C19 1.375(4) . ? C18 H18 0.93 . ? C20 C19 1.379(4) . ? C20 C21 1.393(4) . ? C20 H20 0.93 . ? C19 H19 0.93 . ? C21 H21 0.93 . ? C22 C27 1.392(3) . ? C22 C23 1.400(3) . ? C23 C24 1.381(3) . ? C23 H23 0.93 . ? C24 C25 1.373(4) . ? C24 H24 0.93 . ? C25 C26 1.378(3) . ? C25 H25 0.93 . ? C26 C27 1.384(3) . ? C26 H26 0.93 . ? C27 H27 0.93 . ? S# P# 1.9642(9) . ? P# C22# 1.817(3) . ? P# C16# 1.835(3) . ? P# C1# 1.893(2) . ? N# C1# 1.452(3) . ? N# C2# 1.467(3) . ? N# H2N 0.79(2) . ? C1# C4# 1.521(3) . ? C1# H1# 0.98 . ? C2# C10# 1.534(3) . ? C2# C3# 1.534(3) . ? C2# H2# 0.98 . ? C3# H3A# 0.96 . ? C3# H3B# 0.96 . ? C3# H3C# 0.96 . ? C4# C9# 1.381(3) . ? C4# C5# 1.388(3) . ? C5# C6# 1.390(4) . ? C5# H5# 0.93 . ? C6# C7# 1.375(4) . ? C6# H6# 0.93 . ? C7# C8# 1.380(4) . ? C7# H7# 0.93 . ? C8# C9# 1.390(4) . ? C8# H8# 0.93 . ? C9# H9# 0.93 . ? C10# C15# 1.370(4) . ? C10# C11# 1.379(3) . ? C11# C12# 1.388(3) . ? C11# H11# 0.93 . ? C12# C13# 1.385(4) . ? C12# H12# 0.93 . ? C13# C14# 1.374(4) . ? C13# H13# 0.93 . ? C14# C15# 1.391(3) . ? C14# H14# 0.93 . ? C15# H15# 0.93 . ? C16# C21# 1.384(3) . ? C16# C17# 1.393(4) . ? C17# C18# 1.384(4) . ? C17# H17# 0.93 . ? C18# C19# 1.379(4) . ? C18# H18# 0.93 . ? C19# C20# 1.379(4) . ? C19# H19# 0.93 . ? C20# C21# 1.377(4) . ? C20# H20# 0.93 . ? C21# H21# 0.93 . ? C22# C27# 1.393(3) . ? C22# C23# 1.397(3) . ? C23# C24# 1.372(3) . ? C23# H23# 0.93 . ? C24# C25# 1.385(4) . ? C24# H24# 0.93 . ? C25# C26# 1.381(3) . ? C25# H25# 0.93 . ? C26# C27# 1.377(4) . ? C26# H26# 0.93 . ? C27# H27# 0.93 . ? 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 C22 P C16 105.74(11) . . ? C22 P C1 106.92(11) . . ? C16 P C1 105.03(11) . . ? C22 P S 112.99(9) . . ? C16 P S 112.85(8) . . ? C1 P S 112.69(8) . . ? C1 N C2 114.82(18) . . ? C1 N H1N 106.9(15) . . ? C2 N H1N 108.0(14) . . ? N C1 C4 118.2(2) . . ? N C1 P 103.90(14) . . ? C4 C1 P 113.10(16) . . ? N C1 H1 107 . . ? C4 C1 H1 107 . . ? P C1 H1 107 . . ? N C2 C3 107.41(18) . . ? N C2 C10 111.00(19) . . ? C3 C2 C10 110.9(2) . . ? N C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C10 C2 H2 109.2 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3A 109.5 . . ? H3B C3 H3A 109.5 . . ? C2 C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? C9 C4 C5 118.7(2) . . ? C9 C4 C1 119.6(2) . . ? C5 C4 C1 121.7(2) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.4(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C4 120.7(2) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C15 C10 C11 118.7(2) . . ? C15 C10 C2 120.6(2) . . ? C11 C10 C2 120.6(2) . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C10 C15 C14 120.7(2) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C21 C16 C17 118.5(2) . . ? C21 C16 P 119.27(19) . . ? C17 C16 P 122.23(18) . . ? C18 C17 C16 121.2(2) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 119.6(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C18 C19 C20 120.5(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C16 C21 C20 120.4(2) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C27 C22 C23 119.1(2) . . ? C27 C22 P 118.80(18) . . ? C23 C22 P 122.04(18) . . ? C24 C23 C22 119.9(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C27 120.2(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C22 120.1(2) . . ? C26 C27 H27 120 . . ? C22 C27 H27 120 . . ? C22# P# C16# 105.40(11) . . ? C22# P# C1# 107.86(10) . . ? C16# P# C1# 106.66(11) . . ? C22# P# S# 113.66(8) . . ? C16# P# S# 111.68(8) . . ? C1# P# S# 111.17(8) . . ? C1# N# C2# 117.7(2) . . ? C1# N# H2N 106.1(19) . . ? C2# N# H2N 110(2) . . ? N# C1# C4# 109.9(2) . . ? N# C1# P# 111.32(16) . . ? C4# C1# P# 111.69(17) . . ? N# C1# H1# 107.9 . . ? C4# C1# H1# 107.9 . . ? P# C1# H1# 107.9 . . ? N# C2# C10# 110.4(2) . . ? N# C2# C3# 107.2(2) . . ? C10# C2# C3# 109.7(2) . . ? N# C2# H2# 109.9 . . ? C10# C2# H2# 109.9 . . ? C3# C2# H2# 109.9 . . ? C2# C3# H3A# 109.5 . . ? C2# C3# H3B# 109.5 . . ? H3A# C3# H3B# 109.5 . . ? C2# C3# H3C# 109.5 . . ? H3A# C3# H3C# 109.5 . . ? H3B# C3# H3C# 109.5 . . ? C9# C4# C5# 119.4(2) . . ? C9# C4# C1# 119.8(2) . . ? C5# C4# C1# 120.8(2) . . ? C4# C5# C6# 120.3(2) . . ? C4# C5# H5# 119.9 . . ? C6# C5# H5# 119.9 . . ? C7# C6# C5# 119.8(3) . . ? C7# C6# H6# 120.1 . . ? C5# C6# H6# 120.1 . . ? C6# C7# C8# 120.3(3) . . ? C6# C7# H7# 119.8 . . ? C8# C7# H7# 119.8 . . ? C7# C8# C9# 119.8(2) . . ? C7# C8# H8# 120.1 . . ? C9# C8# H8# 120.1 . . ? C4# C9# C8# 120.4(3) . . ? C4# C9# H9# 119.8 . . ? C8# C9# H9# 119.8 . . ? C15# C10# C11# 119.3(2) . . ? C15# C10# C2# 119.2(2) . . ? C11# C10# C2# 121.3(2) . . ? C10# C11# C12# 120.3(3) . . ? C10# C11# H11# 119.8 . . ? C12# C11# H11# 119.8 . . ? C13# C12# C11# 119.6(2) . . ? C13# C12# H12# 120.2 . . ? C11# C12# H12# 120.2 . . ? C14# C13# C12# 120.3(3) . . ? C14# C13# H13# 119.9 . . ? C12# C13# H13# 119.9 . . ? C13# C14# C15# 119.3(3) . . ? C13# C14# H14# 120.4 . . ? C15# C14# H14# 120.4 . . ? C10# C15# C14# 121.1(2) . . ? C10# C15# H15# 119.5 . . ? C14# C15# H15# 119.5 . . ? C21# C16# C17# 118.6(2) . . ? C21# C16# P# 119.1(2) . . ? C17# C16# P# 122.3(2) . . ? C18# C17# C16# 120.1(3) . . ? C18# C17# H17# 119.9 . . ? C16# C17# H17# 119.9 . . ? C19# C18# C17# 120.4(3) . . ? C19# C18# H18# 119.8 . . ? C17# C18# H18# 119.8 . . ? C18# C19# C20# 119.6(3) . . ? C18# C19# H19# 120.2 . . ? C20# C19# H19# 120.2 . . ? C21# C20# C19# 120.1(3) . . ? C21# C20# H20# 120 . . ? C19# C20# H20# 120 . . ? C20# C21# C16# 121.0(3) . . ? C20# C21# H21# 119.5 . . ? C16# C21# H21# 119.5 . . ? C27# C22# C23# 119.0(2) . . ? C27# C22# P# 119.54(18) . . ? C23# C22# P# 121.41(18) . . ? C24# C23# C22# 120.2(2) . . ? C24# C23# H23# 119.9 . . ? C22# C23# H23# 119.9 . . ? C23# C24# C25# 120.6(2) . . ? C23# C24# H24# 119.7 . . ? C25# C24# H24# 119.7 . . ? C26# C25# C24# 119.5(3) . . ? C26# C25# H25# 120.3 . . ? C24# C25# H25# 120.3 . . ? C27# C26# C25# 120.5(2) . . ? C27# C26# H26# 119.7 . . ? C25# C26# H26# 119.7 . . ? C26# C27# C22# 120.2(2) . . ? C26# C27# H27# 119.9 . . ? C22# C27# H27# 119.9 . . ? 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 H1 C1 P S 163.3 . . . . ? C1 P S H1N -20.1(6) . . . . ? P S H1N C1 17.8(5) . . . . ? S H1N C1 H1 -131.4 . . . . ? H1# C1# P# S# -156.6 . . . . ? C1# P# S# H2N 16.9(6) . . . . ? P# S# H2N C1# -16.3(6) . . . . ? S# H2N C1# H1# 130.5 . . . . ? #==END data_poli19 _database_code_CSD 164810 _audit_creation_date 2000-10-19T16:21:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27 H26 N O P' _chemical_formula_weight 411.46 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.8040(10) _cell_length_b 16.911(3) _cell_length_c 23.518(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2308.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.137 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 4099 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.69 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 4099 _reflns_number_gt 3776 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0365P)^2^+0.4865P] 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_number_reflns 4099 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.473 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(9) _refine_diff_density_max 0.129 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.028 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.15252(8) 0.83978(3) 0.16457(2) 0.03791(13) Uani 1 1 d . . . O O -0.0949(2) 0.86125(8) 0.15909(7) 0.0513(4) Uani 1 1 d . . . N N 0.2705(3) 0.96279(9) 0.10342(7) 0.0403(4) Uani 1 1 d . . . H H 0.131(4) 0.9711(13) 0.1046(9) 0.052 Uiso 1 1 d . . . C1 C 0.3397(3) 0.92646(10) 0.15715(8) 0.0373(4) Uani 1 1 d . . . H1 H 0.487(4) 0.9057(12) 0.1543(8) 0.048 Uiso 1 1 d . . . C2 C 0.3971(3) 1.03513(11) 0.08799(9) 0.0456(5) Uani 1 1 d . . . H2 H 0.4039 1.0697 0.1214 0.059 Uiso 1 1 calc R . . C3 C 0.6402(4) 1.01394(17) 0.07090(14) 0.0814(8) Uani 1 1 d . . . H3A H 0.7155 0.9876 0.1019 0.106 Uiso 1 1 calc R . . H3B H 0.7233 1.0612 0.0615 0.106 Uiso 1 1 calc R . . H3C H 0.6362 0.9795 0.0385 0.106 Uiso 1 1 calc R . . C4 C 0.2646(4) 1.07683(11) 0.04196(9) 0.0450(5) Uani 1 1 d . . . C5 C 0.1595(4) 1.14841(12) 0.05297(11) 0.0600(6) Uani 1 1 d . . . H5 H 0.1785 1.1712 0.0887 0.078 Uiso 1 1 calc R . . C6 C 0.0292(5) 1.18695(17) 0.01375(14) 0.0795(8) Uani 1 1 d . . . H6 H -0.039 1.2351 0.0227 0.103 Uiso 1 1 calc R . . C7 C -0.0001(6) 1.1548(2) -0.03815(16) 0.0930(10) Uani 1 1 d . . . H7 H -0.0898 1.1809 -0.065 0.121 Uiso 1 1 calc R . . C8 C 0.0997(7) 1.0848(2) -0.05156(13) 0.1095(12) Uani 1 1 d . . . H8 H 0.0801 1.0632 -0.0876 0.142 Uiso 1 1 calc R . . C9 C 0.2326(6) 1.04507(17) -0.01087(11) 0.0848(9) Uani 1 1 d . . . H9 H 0.2996 0.9967 -0.0199 0.11 Uiso 1 1 calc R . . C10 C 0.3300(3) 0.97772(10) 0.21015(8) 0.0402(4) Uani 1 1 d . . . C11 C 0.5120(4) 0.97666(13) 0.24844(10) 0.0524(5) Uani 1 1 d . . . H11 H 0.6407 0.9456 0.2409 0.068 Uiso 1 1 calc R . . C12 C 0.5042(5) 1.02124(16) 0.29779(10) 0.0677(7) Uani 1 1 d . . . H12 H 0.6269 1.0197 0.3232 0.088 Uiso 1 1 calc R . . C13 C 0.3168(5) 1.06747(15) 0.30929(11) 0.0716(7) Uani 1 1 d . . . H13 H 0.3112 1.0969 0.3427 0.093 Uiso 1 1 calc R . . C14 C 0.1359(5) 1.07045(15) 0.27132(11) 0.0700(7) Uani 1 1 d . . . H14 H 0.0096 1.1027 0.2788 0.091 Uiso 1 1 calc R . . C15 C 0.1420(4) 1.02564(12) 0.22224(10) 0.0550(5) Uani 1 1 d . . . H15 H 0.0188 1.0276 0.197 0.071 Uiso 1 1 calc R . . C16 C 0.2163(3) 0.79637(11) 0.23299(8) 0.0424(5) Uani 1 1 d . . . C17 C 0.4072(4) 0.75056(16) 0.24274(10) 0.0659(7) Uani 1 1 d . . . H17 H 0.5113 0.7417 0.2133 0.086 Uiso 1 1 calc R . . C18 C 0.4475(5) 0.71757(17) 0.29516(11) 0.0801(8) Uani 1 1 d . . . H18 H 0.5775 0.6865 0.3009 0.104 Uiso 1 1 calc R . . C19 C 0.2977(5) 0.73028(15) 0.33861(11) 0.0764(7) Uani 1 1 d . . . H19 H 0.3236 0.7072 0.3739 0.099 Uiso 1 1 calc R . . C20 C 0.1104(5) 0.77683(19) 0.33030(12) 0.0901(9) Uani 1 1 d . . . H20 H 0.0106 0.7869 0.3604 0.117 Uiso 1 1 calc R . . C21 C 0.0662(5) 0.80967(17) 0.27721(11) 0.0722(7) Uani 1 1 d . . . H21 H -0.0644 0.8405 0.2716 0.094 Uiso 1 1 calc R . . C22 C 0.2468(3) 0.76714(11) 0.11336(8) 0.0416(4) Uani 1 1 d . . . C23 C 0.1010(4) 0.70398(14) 0.10442(11) 0.0689(7) Uani 1 1 d . . . H23 H -0.0406 0.7021 0.1229 0.09 Uiso 1 1 calc R . . C24 C 0.1643(6) 0.64347(16) 0.06811(14) 0.0917(9) Uani 1 1 d . . . H24 H 0.0667 0.6004 0.0631 0.119 Uiso 1 1 calc R . . C25 C 0.3696(5) 0.64635(15) 0.03945(12) 0.0759(7) Uani 1 1 d . . . H25 H 0.4099 0.6059 0.0145 0.099 Uiso 1 1 calc R . . C26 C 0.5141(4) 0.70852(15) 0.04758(11) 0.0667(6) Uani 1 1 d . . . H26 H 0.6534 0.7106 0.0281 0.087 Uiso 1 1 calc R . . C27 C 0.4551(4) 0.76900(13) 0.08478(10) 0.0549(5) Uani 1 1 d . . . H27 H 0.5561 0.8109 0.0905 0.071 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 P 0.0317(2) 0.0362(2) 0.0458(3) 0.0043(2) -0.0016(2) -0.0012(2) O 0.0329(6) 0.0531(8) 0.0678(9) 0.0066(7) -0.0042(7) 0.0003(6) N 0.0351(8) 0.0373(8) 0.0484(9) 0.0070(7) -0.0042(8) -0.0039(7) C1 0.0300(8) 0.0363(8) 0.0454(10) 0.0026(8) -0.0007(9) 0.0012(8) C2 0.0462(11) 0.0376(10) 0.0531(12) 0.0053(8) -0.0015(9) -0.0088(9) C3 0.0426(12) 0.0861(17) 0.115(2) 0.0399(17) 0.0108(15) -0.0006(14) C4 0.0478(11) 0.0380(10) 0.0492(11) 0.0048(9) 0.0033(10) -0.0024(9) C5 0.0599(13) 0.0472(11) 0.0728(15) 0.0042(10) -0.0015(12) 0.0026(12) C6 0.0738(17) 0.0601(15) 0.105(2) 0.0244(16) -0.0076(17) 0.0071(13) C7 0.093(2) 0.088(2) 0.097(2) 0.043(2) -0.0153(19) 0.0064(19) C8 0.143(3) 0.130(3) 0.0555(17) -0.0020(18) -0.0229(19) 0.014(3) C9 0.120(2) 0.0763(17) 0.0582(15) -0.0103(13) -0.0077(16) 0.0247(16) C10 0.0386(9) 0.0362(9) 0.0459(10) 0.0028(8) 0.0046(9) -0.0021(9) C11 0.0465(11) 0.0560(12) 0.0548(12) -0.0036(10) -0.0047(10) 0.0029(11) C12 0.0720(16) 0.0777(16) 0.0533(14) -0.0111(13) -0.0072(13) -0.0053(14) C13 0.0865(19) 0.0710(15) 0.0572(14) -0.0202(12) 0.0151(14) -0.0084(15) C14 0.0650(15) 0.0654(14) 0.0795(17) -0.0162(13) 0.0164(15) 0.0072(14) C15 0.0465(11) 0.0536(11) 0.0647(13) -0.0056(10) 0.0021(11) 0.0036(11) C16 0.0437(11) 0.0356(9) 0.0480(11) 0.0036(8) 0.0013(9) -0.0034(8) C17 0.0690(16) 0.0804(16) 0.0483(12) 0.0109(12) 0.0023(11) 0.0286(13) C18 0.0881(19) 0.0894(19) 0.0628(16) 0.0167(14) -0.0077(15) 0.0365(16) C19 0.104(2) 0.0739(15) 0.0511(13) 0.0181(13) 0.0036(15) 0.0124(15) C20 0.098(2) 0.109(2) 0.0623(16) 0.0248(16) 0.0313(17) 0.0240(18) C21 0.0655(15) 0.0843(17) 0.0670(16) 0.0225(14) 0.0188(12) 0.0231(14) C22 0.0436(10) 0.0373(9) 0.0440(11) 0.0039(8) -0.0061(9) -0.0011(8) C23 0.0614(15) 0.0636(14) 0.0816(17) -0.0159(13) 0.0093(13) -0.0226(12) C24 0.095(2) 0.0670(16) 0.113(2) -0.0362(16) 0.005(2) -0.0290(17) C25 0.0770(18) 0.0673(15) 0.0834(17) -0.0328(14) -0.0052(16) 0.0027(15) C26 0.0564(13) 0.0730(16) 0.0709(16) -0.0207(13) 0.0037(13) 0.0025(13) C27 0.0464(11) 0.0536(12) 0.0648(14) -0.0101(11) 0.0051(11) -0.0078(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O 1.4870(13) . ? P C22 1.805(2) . ? P C16 1.807(2) . ? P C1 1.8329(18) . ? N C1 1.461(2) . ? N C2 1.472(2) . ? N H 0.82(2) . ? C1 C10 1.519(3) . ? C1 H1 0.93(2) . ? C2 C4 1.503(3) . ? C2 C3 1.510(3) . ? C2 H2 0.98 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 C9 1.366(3) . ? C4 C5 1.380(3) . ? C5 C6 1.359(3) . ? C5 H5 0.93 . ? C6 C7 1.347(4) . ? C6 H6 0.93 . ? C7 C8 1.355(5) . ? C7 H7 0.93 . ? C8 C9 1.401(4) . ? C8 H8 0.93 . ? C9 H9 0.93 . ? C10 C11 1.388(3) . ? C10 C15 1.388(3) . ? C11 C12 1.385(3) . ? C11 H11 0.93 . ? C12 C13 1.366(4) . ? C12 H12 0.93 . ? C13 C14 1.379(4) . ? C13 H13 0.93 . ? C14 C15 1.381(3) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C16 C17 1.372(3) . ? C16 C21 1.375(3) . ? C17 C18 1.373(3) . ? C17 H17 0.93 . ? C18 C19 1.358(4) . ? C18 H18 0.93 . ? C19 C20 1.357(4) . ? C19 H19 0.93 . ? C20 C21 1.390(4) . ? C20 H20 0.93 . ? C21 H21 0.93 . ? C22 C23 1.379(3) . ? C22 C27 1.384(3) . ? C23 C24 1.383(4) . ? C23 H23 0.93 . ? C24 C25 1.370(4) . ? C24 H24 0.93 . ? C25 C26 1.358(3) . ? C25 H25 0.93 . ? C26 C27 1.389(3) . ? C26 H26 0.93 . ? C27 H27 0.93 . ? 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 O P C22 113.63(9) . . ? O P C16 111.98(9) . . ? C22 P C16 104.81(9) . . ? O P C1 111.65(8) . . ? C22 P C1 107.52(9) . . ? C16 P C1 106.76(9) . . ? C1 N C2 115.18(15) . . ? C1 N H 108.3(16) . . ? C2 N H 111.0(16) . . ? N C1 C10 117.35(14) . . ? N C1 P 104.82(12) . . ? C10 C1 P 110.86(13) . . ? N C1 H1 110.5(12) . . ? C10 C1 H1 108.0(13) . . ? P C1 H1 104.5(12) . . ? N C2 C4 108.18(16) . . ? N C2 C3 109.55(18) . . ? C4 C2 C3 113.43(19) . . ? N C2 H2 108.5 . . ? C4 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C9 C4 C5 117.1(2) . . ? C9 C4 C2 122.7(2) . . ? C5 C4 C2 120.2(2) . . ? C6 C5 C4 122.6(2) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C7 C6 C5 119.4(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C4 C9 C8 120.5(3) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C15 118.20(19) . . ? C11 C10 C1 119.78(18) . . ? C15 C10 C1 122.02(18) . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C14 C15 C10 120.8(2) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C17 C16 C21 118.5(2) . . ? C17 C16 P 122.95(16) . . ? C21 C16 P 118.51(16) . . ? C16 C17 C18 121.1(2) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.6(2) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 119.8(2) . . ? C16 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C27 118.7(2) . . ? C23 C22 P 116.28(17) . . ? C27 C22 P 124.98(15) . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 120.6(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 119.7(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C22 C27 C26 120.3(2) . . ? C22 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? 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 H1 C1 P O -169.6(13) . . . . ? C1 P O H 24.5(5) . . . . ? P O H N 3.7(18) . . . . ? O H N C1 -35.9(17) . . . . ? H N C1 H1 167(2) . . . . ?