Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_compound3 _database_code_CSD 157568 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Sudha Kumaraswamy' 'Praveen Kommana' 'N. Satish Kumar' 'K. C. Kumara Swamy' _publ_contact_author_name 'Dr K. C. Kumara Swamy' _publ_contact_author_address ; Dr K. C. Kumara Swamy School of Chemistry University of Hyderabad Gachibowli Hyderabad A. P. 500046 INDIA ; _publ_contact_author_email 'KCKSSC@UOHYD.ERNET.IN' _publ_section_title ; Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C107 H136.50 N13.50 O16 P4' _chemical_formula_weight 1991.68 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.616(4) _cell_length_b 19.288(4) _cell_length_c 23.112(8) _cell_angle_alpha 114.26(2) _cell_angle_beta 103.91(2) _cell_angle_gamma 96.55(2) _cell_volume 5597(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2122 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19610 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 24.98 _reflns_number_total 19610 _reflns_number_gt 7781 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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 w=1/[\s^2^(Fo^2^)+(0.1117P)^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_coef 0.0019(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 19610 _refine_ls_number_parameters 1374 _refine_ls_number_restraints 132 _refine_ls_R_factor_all 0.1464 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.2290 _refine_ls_wR_factor_gt 0.1651 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.984 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.23024(9) 0.13125(7) 0.42152(6) 0.0537(3) Uani 1 d . . . P2 P -0.08149(9) 0.12760(7) 0.35710(6) 0.0524(3) Uani 1 d . . . O1 O 0.2169(2) 0.06999(17) 0.34829(14) 0.0599(8) Uani 1 d . . . O2 O 0.3404(2) 0.15943(17) 0.45744(14) 0.0533(7) Uani 1 d . . . O3 O 0.0871(2) 0.37789(18) 0.49828(17) 0.0739(10) Uani 1 d . . . O4 O 0.1511(3) 0.3577(2) 0.41670(19) 0.0921(12) Uani 1 d . . . O5 O -0.2111(2) 0.2429(2) 0.34968(18) 0.0769(10) Uani 1 d . . . O6 O -0.0873(3) 0.3460(2) 0.3888(2) 0.1043(14) Uani 1 d . . . O7 O -0.1452(2) 0.08352(16) 0.28065(13) 0.0523(7) Uani 1 d . . . O8 O -0.1457(2) 0.08939(17) 0.38776(14) 0.0595(8) Uani 1 d . . . N1 N 0.1987(3) 0.0698(2) 0.4509(2) 0.0747(12) Uani 1 d . . . N2 N 0.1453(5) 0.0811(3) 0.4838(3) 0.114(2) Uani 1 d . . . N3 N 0.0965(8) 0.0886(5) 0.5153(5) 0.214(5) Uani 1 d . . . N4 N 0.1864(3) 0.2032(2) 0.43521(18) 0.0569(9) Uani 1 d . . . N5 N 0.0875(3) 0.1937(2) 0.40633(17) 0.0539(9) Uani 1 d . . . N6 N 0.0277(3) 0.1189(2) 0.37665(19) 0.0605(10) Uani 1 d . . . C101 C 0.2891(3) 0.0562(3) 0.3155(2) 0.0559(11) Uani 1 d . . . C102 C 0.2954(3) -0.0215(3) 0.2822(2) 0.0598(12) Uani 1 d . . . C103 C 0.3644(4) -0.0312(3) 0.2485(2) 0.0694(14) Uani 1 d . . . H103 H 0.3703 -0.0818 0.2246 0.083 Uiso 1 calc R . . C104 C 0.4242(4) 0.0297(3) 0.2486(2) 0.0667(14) Uani 1 d . . . C105 C 0.4141(4) 0.1037(3) 0.2820(2) 0.0679(14) Uani 1 d . . . H105 H 0.4542 0.1453 0.2827 0.082 Uiso 1 calc R . . C106 C 0.3449(3) 0.1187(3) 0.3154(2) 0.0575(12) Uani 1 d . . . C107 C 0.3372(3) 0.2022(3) 0.3509(2) 0.0596(12) Uani 1 d . . . H10A H 0.2721 0.2018 0.3539 0.072 Uiso 1 calc R . . H10B H 0.3471 0.2287 0.3245 0.072 Uiso 1 calc R . . C108 C 0.4093(3) 0.2477(3) 0.4204(2) 0.0545(11) Uani 1 d . . . C109 C 0.4801(4) 0.3113(3) 0.4343(3) 0.0652(13) Uani 1 d . . . H109 H 0.4821 0.3254 0.4006 0.078 Uiso 1 calc R . . C110 C 0.5477(4) 0.3544(3) 0.4969(3) 0.0719(14) Uani 1 d . . . C111 C 0.5430(4) 0.3325(3) 0.5465(3) 0.0747(15) Uani 1 d . . . H111 H 0.5881 0.3620 0.5890 0.090 Uiso 1 calc R . . C112 C 0.4748(3) 0.2693(3) 0.5360(2) 0.0579(12) Uani 1 d . . . C113 C 0.4088(3) 0.2280(3) 0.4714(2) 0.0511(11) Uani 1 d . . . C114 C 0.2362(4) -0.0921(3) 0.2828(3) 0.0718(14) Uani 1 d . . . C115 C 0.2720(5) -0.0875(4) 0.3512(3) 0.109(2) Uani 1 d . . . H11A H 0.3413 -0.0803 0.3644 0.164 Uiso 1 calc R . . H11B H 0.2423 -0.1352 0.3502 0.164 Uiso 1 calc R . . H11C H 0.2553 -0.0441 0.3828 0.164 Uiso 1 calc R . . C116 C 0.2470(5) -0.1701(3) 0.2318(4) 0.123(3) Uani 1 d . . . H11D H 0.2337 -0.1709 0.1887 0.185 Uiso 1 calc R . . H11E H 0.2020 -0.2127 0.2288 0.185 Uiso 1 calc R . . H11F H 0.3120 -0.1754 0.2460 0.185 Uiso 1 calc R . . C117 C 0.1277(4) -0.0937(4) 0.2644(4) 0.109(2) Uani 1 d . . . H11G H 0.1175 -0.0469 0.2965 0.163 Uiso 1 calc R . . H11H H 0.0920 -0.1387 0.2644 0.163 Uiso 1 calc R . . H11I H 0.1057 -0.0965 0.2207 0.163 Uiso 1 calc R . . C118 C 0.4983(5) 0.0142(4) 0.2117(3) 0.0948(19) Uani 1 d . . . H11J H 0.5529 0.0587 0.2339 0.142 Uiso 1 calc R . . H11K H 0.4693 0.0054 0.1665 0.142 Uiso 1 calc R . . H11L H 0.5197 -0.0312 0.2112 0.142 Uiso 1 calc R . . C119 C 0.6206(5) 0.4269(4) 0.5118(4) 0.112(2) Uani 1 d . . . H11M H 0.6402 0.4184 0.4731 0.168 Uiso 1 calc R . . H11N H 0.6764 0.4373 0.5488 0.168 Uiso 1 calc R . . H11O H 0.5915 0.4708 0.5230 0.168 Uiso 1 calc R . . C120 C 0.4700(4) 0.2494(3) 0.5939(2) 0.0685(13) Uani 1 d . . . C121 C 0.4837(5) 0.1667(4) 0.5774(3) 0.098(2) Uani 1 d . . . H12A H 0.4796 0.1550 0.6134 0.146 Uiso 1 calc R . . H12B H 0.5461 0.1636 0.5715 0.146 Uiso 1 calc R . . H12C H 0.4338 0.1296 0.5369 0.146 Uiso 1 calc R . . C122 C 0.3737(4) 0.2567(4) 0.6069(3) 0.0860(17) Uani 1 d . . . H12D H 0.3664 0.3090 0.6179 0.129 Uiso 1 calc R . . H12E H 0.3723 0.2454 0.6436 0.129 Uiso 1 calc R . . H12F H 0.3216 0.2202 0.5676 0.129 Uiso 1 calc R . . C123 C 0.5505(5) 0.3059(4) 0.6592(3) 0.117(2) Uani 1 d . . . H12G H 0.5483 0.3589 0.6687 0.175 Uiso 1 calc R . . H12H H 0.6125 0.2979 0.6546 0.175 Uiso 1 calc R . . H12I H 0.5411 0.2962 0.6952 0.175 Uiso 1 calc R . . C124 C 0.0448(3) 0.2515(2) 0.4131(2) 0.0529(11) Uani 1 d . . . C125 C 0.1020(4) 0.3342(3) 0.4420(2) 0.0583(12) Uani 1 d . . . C126 C 0.1173(5) 0.4631(3) 0.5250(4) 0.111(2) Uani 1 d . . . H12J H 0.1699 0.4841 0.5662 0.166 Uiso 1 calc R . . H12K H 0.0636 0.4856 0.5331 0.166 Uiso 1 calc R . . H12L H 0.1382 0.4753 0.4933 0.166 Uiso 1 calc R . . C127 C -0.0576(3) 0.2277(3) 0.3873(2) 0.0544(11) Uani 1 d . . . C128 C -0.1168(4) 0.2780(3) 0.3770(2) 0.0654(13) Uani 1 d . . . C129 C -0.2767(4) 0.2904(4) 0.3386(3) 0.105(2) Uani 1 d . . . H12M H -0.2545 0.3423 0.3752 0.158 Uiso 1 calc R . . H12N H -0.3407 0.2673 0.3353 0.158 Uiso 1 calc R . . H12O H -0.2785 0.2930 0.2977 0.158 Uiso 1 calc R . . C201 C -0.1258(3) 0.0265(2) 0.2266(2) 0.0504(10) Uani 1 d . . . C202 C -0.1321(3) 0.0374(3) 0.1698(2) 0.0590(12) Uani 1 d . . . C203 C -0.1211(4) -0.0257(3) 0.1165(2) 0.0652(13) Uani 1 d . . . H203 H -0.1234 -0.0208 0.0778 0.078 Uiso 1 calc R . . C204 C -0.1068(3) -0.0957(3) 0.1167(2) 0.0636(13) Uani 1 d . . . C205 C -0.1025(3) -0.1024(3) 0.1740(2) 0.0605(12) Uani 1 d . . . H205 H -0.0923 -0.1483 0.1757 0.073 Uiso 1 calc R . . C206 C -0.1130(3) -0.0418(2) 0.2300(2) 0.0518(11) Uani 1 d . . . C207 C -0.1119(3) -0.0518(3) 0.2915(2) 0.0589(12) Uani 1 d . . . H20A H -0.0992 -0.1023 0.2850 0.071 Uiso 1 calc R . . H20B H -0.0594 -0.0117 0.3295 0.071 Uiso 1 calc R . . C208 C -0.2056(3) -0.0467(3) 0.3072(2) 0.0565(11) Uani 1 d . . . C209 C -0.2821(4) -0.1118(3) 0.2734(2) 0.0621(12) Uani 1 d . . . H209 H -0.2736 -0.1577 0.2420 0.075 Uiso 1 calc R . . C210 C -0.3709(4) -0.1119(3) 0.2840(3) 0.0647(13) Uani 1 d . . . C211 C -0.3791(4) -0.0463(3) 0.3350(3) 0.0687(14) Uani 1 d . . . H211 H -0.4368 -0.0474 0.3453 0.082 Uiso 1 calc R . . C212 C -0.3047(4) 0.0225(3) 0.3724(2) 0.0622(12) Uani 1 d . . . C213 C -0.2206(3) 0.0200(3) 0.3541(2) 0.0564(11) Uani 1 d . . . C214 C -0.1456(5) 0.1130(3) 0.1669(3) 0.0754(15) Uani 1 d . . . C215 C -0.0567(6) 0.1797(3) 0.2172(3) 0.113(2) Uani 1 d . . . H21A H -0.0663 0.2280 0.2170 0.170 Uiso 1 calc R . . H21B H 0.0001 0.1686 0.2048 0.170 Uiso 1 calc R . . H21C H -0.0482 0.1843 0.2612 0.170 Uiso 1 calc R . . C216 C -0.1541(5) 0.1063(3) 0.0967(3) 0.101(2) Uani 1 d . . . H21D H -0.2085 0.0642 0.0639 0.151 Uiso 1 calc R . . H21E H -0.0957 0.0960 0.0864 0.151 Uiso 1 calc R . . H21F H -0.1634 0.1545 0.0961 0.151 Uiso 1 calc R . . C217 C -0.2401(5) 0.1318(4) 0.1810(3) 0.108(2) Uani 1 d . . . H21G H -0.2480 0.1791 0.1781 0.162 Uiso 1 calc R . . H21H H -0.2367 0.1386 0.2251 0.162 Uiso 1 calc R . . H21I H -0.2943 0.0894 0.1486 0.162 Uiso 1 calc R . . C218 C -0.0961(4) -0.1598(3) 0.0566(3) 0.0790(16) Uani 1 d . . . H21J H -0.0444 -0.1818 0.0703 0.118 Uiso 1 calc R . . H21K H -0.0813 -0.1391 0.0277 0.118 Uiso 1 calc R . . H21L H -0.1556 -0.1998 0.0331 0.118 Uiso 1 calc R . . C219 C -0.4541(4) -0.1837(3) 0.2425(3) 0.0893(17) Uani 1 d . . . H21M H -0.4296 -0.2299 0.2331 0.134 Uiso 1 calc R . . H21N H -0.4866 -0.1835 0.2012 0.134 Uiso 1 calc R . . H21O H -0.4992 -0.1833 0.2667 0.134 Uiso 1 calc R . . C220 C -0.3194(4) 0.0909(3) 0.4302(3) 0.0765(15) Uani 1 d . . . C221 C -0.3183(6) 0.1619(4) 0.4174(4) 0.130(3) Uani 1 d . . . H22A H -0.2526 0.1866 0.4254 0.194 Uiso 1 calc R . . H22B H -0.3458 0.1982 0.4469 0.194 Uiso 1 calc R . . H22C H -0.3558 0.1459 0.3718 0.194 Uiso 1 calc R . . C222 C -0.2422(6) 0.1112(5) 0.4940(3) 0.148(3) Uani 1 d . . . H22D H -0.1800 0.1137 0.4871 0.222 Uiso 1 calc R . . H22E H -0.2543 0.0718 0.5083 0.222 Uiso 1 calc R . . H22F H -0.2428 0.1610 0.5278 0.222 Uiso 1 calc R . . C223 C -0.4190(6) 0.0720(5) 0.4383(4) 0.161(4) Uani 1 d . . . H22G H -0.4686 0.0511 0.3957 0.241 Uiso 1 calc R . . H22H H -0.4308 0.1190 0.4690 0.241 Uiso 1 calc R . . H22I H -0.4200 0.0342 0.4553 0.241 Uiso 1 calc R . . P3 P 0.30422(9) 0.49463(7) 0.81235(6) 0.0592(3) Uani 1 d . . . P4 P 0.60945(8) 0.57610(7) 0.82385(6) 0.0497(3) Uani 1 d . . . O9 O 0.1961(2) 0.45005(18) 0.78284(15) 0.0595(8) Uani 1 d . . . O10 O 0.3115(2) 0.57653(18) 0.86821(16) 0.0656(9) Uani 1 d . . . O11 O 0.4053(2) 0.44178(19) 0.61062(15) 0.0739(10) Uani 1 d . . . O12 O 0.3460(3) 0.5473(2) 0.64452(18) 0.0962(13) Uani 1 d . . . O13 O 0.7142(2) 0.6155(2) 0.73470(16) 0.0676(9) Uani 1 d . . . O14 O 0.5784(3) 0.5788(3) 0.64915(19) 0.0972(13) Uani 1 d . . . O15 O 0.6684(2) 0.66352(15) 0.87312(13) 0.0502(7) Uani 1 d . . . O16 O 0.6837(2) 0.52904(16) 0.84258(14) 0.0531(7) Uani 1 d . . . N7 N 0.3494(4) 0.4517(3) 0.8591(3) 0.0866(14) Uani 1 d . . . N8 N 0.4132(5) 0.4194(3) 0.8487(3) 0.1072(18) Uani 1 d . . . N9 N 0.4755(6) 0.3873(5) 0.8413(5) 0.174(3) Uani 1 d . . . N10 N 0.3435(3) 0.4868(2) 0.75417(18) 0.0610(10) Uani 1 d . . . N11 N 0.4381(3) 0.5255(2) 0.76766(18) 0.0560(9) Uani 1 d . . . N12 N 0.5054(3) 0.5479(2) 0.82975(17) 0.0583(10) Uani 1 d . . . C301 C 0.1219(3) 0.4385(3) 0.7250(2) 0.0567(12) Uani 1 d . . . C302 C 0.0654(3) 0.3626(3) 0.6852(2) 0.0605(12) Uani 1 d . . . C303 C -0.0143(4) 0.3548(4) 0.6333(3) 0.0809(16) Uani 1 d . . . H303 H -0.0551 0.3053 0.6049 0.097 Uiso 1 calc R . . C304 C -0.0353(5) 0.4172(4) 0.6222(3) 0.0887(17) Uani 1 d . . . C305 C 0.0262(4) 0.4910(4) 0.6637(3) 0.0799(16) Uani 1 d . . . H305 H 0.0132 0.5332 0.6561 0.096 Uiso 1 calc R . . C306 C 0.1059(4) 0.5030(3) 0.7156(2) 0.0621(12) Uani 1 d . . . C307 C 0.1720(4) 0.5848(3) 0.7596(2) 0.0679(13) Uani 1 d . . . H30A H 0.2381 0.5825 0.7601 0.081 Uiso 1 calc R . . H30B H 0.1527 0.6189 0.7400 0.081 Uiso 1 calc R . . C308 C 0.1697(4) 0.6202(2) 0.8310(2) 0.0585(12) Uani 1 d . . . C309 C 0.0973(4) 0.6587(3) 0.8456(3) 0.0692(14) Uani 1 d . . . H309 H 0.0513 0.6612 0.8113 0.083 Uiso 1 calc R . . C310 C 0.0922(4) 0.6930(3) 0.9096(3) 0.0708(14) Uani 1 d . . . C311 C 0.1619(4) 0.6880(3) 0.9591(3) 0.0744(15) Uani 1 d . . . H311 H 0.1596 0.7124 1.0026 0.089 Uiso 1 calc R . . C312 C 0.2355(3) 0.6489(3) 0.9486(2) 0.0601(12) Uani 1 d . . . C313 C 0.2356(4) 0.6141(3) 0.8820(3) 0.0604(12) Uani 1 d . . . C314 C 0.0873(4) 0.2911(3) 0.6939(3) 0.0716(14) Uani 1 d . . . C315 C 0.1843(4) 0.2796(3) 0.6830(4) 0.104(2) Uani 1 d . . . H31A H 0.1837 0.2775 0.6406 0.156 Uiso 1 calc R . . H31B H 0.1949 0.2315 0.6832 0.156 Uiso 1 calc R . . H31C H 0.2357 0.3226 0.7182 0.156 Uiso 1 calc R . . C316 C 0.0104(5) 0.2154(3) 0.6421(3) 0.105(2) Uani 1 d . . . H31D H 0.0061 0.2083 0.5978 0.157 Uiso 1 calc R . . H31E H -0.0514 0.2191 0.6489 0.157 Uiso 1 calc R . . H31F H 0.0288 0.1715 0.6472 0.157 Uiso 1 calc R . . C317 C 0.0861(5) 0.2993(3) 0.7623(3) 0.0930(18) Uani 1 d . . . H31G H 0.0968 0.2527 0.7656 0.140 Uiso 1 calc R . . H31H H 0.0242 0.3069 0.7675 0.140 Uiso 1 calc R . . H31I H 0.1364 0.3436 0.7968 0.140 Uiso 1 calc R . . C318 C -0.1233(6) 0.4044(5) 0.5649(4) 0.143(3) Uani 1 d . . . H31J H -0.1469 0.4512 0.5761 0.215 Uiso 1 calc R . . H31K H -0.1734 0.3618 0.5571 0.215 Uiso 1 calc R . . H31L H -0.1052 0.3921 0.5251 0.215 Uiso 1 calc R . . C319 C 0.0142(5) 0.7348(3) 0.9253(3) 0.100(2) Uani 1 d . . . H31M H -0.0309 0.7046 0.9352 0.151 Uiso 1 calc R . . H31N H -0.0194 0.7414 0.8874 0.151 Uiso 1 calc R . . H31O H 0.0429 0.7853 0.9633 0.151 Uiso 1 calc R . . C320 C 0.3061(4) 0.6409(3) 1.0053(3) 0.0752(15) Uani 1 d . . . C321 C 0.4123(4) 0.6606(4) 1.0091(3) 0.0970(19) Uani 1 d . . . H32A H 0.4532 0.6598 1.0480 0.145 Uiso 1 calc R . . H32B H 0.4286 0.7118 1.0119 0.145 Uiso 1 calc R . . H32C H 0.4220 0.6226 0.9697 0.145 Uiso 1 calc R . . C322 C 0.2781(5) 0.5575(4) 0.9961(3) 0.101(2) Uani 1 d . . . H32D H 0.2848 0.5214 0.9548 0.151 Uiso 1 calc R . . H32E H 0.2120 0.5459 0.9951 0.151 Uiso 1 calc R . . H32F H 0.3199 0.5529 1.0326 0.151 Uiso 1 calc R . . C323 C 0.3007(5) 0.6967(4) 1.0741(3) 0.110(2) Uani 1 d . . . H32G H 0.3472 0.6919 1.1086 0.165 Uiso 1 calc R . . H32H H 0.2366 0.6835 1.0761 0.165 Uiso 1 calc R . . H32I H 0.3148 0.7497 1.0804 0.165 Uiso 1 calc R . . C324 C 0.4699(3) 0.5314(2) 0.7209(2) 0.0491(10) Uani 1 d . . . C325 C 0.4004(4) 0.5092(3) 0.6549(2) 0.0610(12) Uani 1 d . . . C326 C 0.3396(5) 0.4111(4) 0.5428(3) 0.108(2) Uani 1 d . . . H32J H 0.2776 0.3845 0.5396 0.161 Uiso 1 calc R . . H32K H 0.3659 0.3751 0.5121 0.161 Uiso 1 calc R . . H32L H 0.3319 0.4536 0.5320 0.161 Uiso 1 calc R . . C327 C 0.5714(3) 0.5599(3) 0.7423(2) 0.0508(11) Uani 1 d . . . C328 C 0.6193(4) 0.5846(3) 0.7030(3) 0.0616(12) Uani 1 d . . . C329 C 0.7696(4) 0.6370(4) 0.6979(3) 0.0925(19) Uani 1 d . . . H32M H 0.7837 0.5912 0.6674 0.139 Uiso 1 calc R . . H32N H 0.8292 0.6744 0.7286 0.139 Uiso 1 calc R . . H32O H 0.7325 0.6598 0.6733 0.139 Uiso 1 calc R . . C401 C 0.6527(3) 0.7182(2) 0.9298(2) 0.0479(10) Uani 1 d . . . C402 C 0.6448(3) 0.7911(3) 0.9342(2) 0.0553(11) Uani 1 d . . . C403 C 0.6361(3) 0.8449(3) 0.9947(2) 0.0607(12) Uani 1 d . . . H403 H 0.6312 0.8947 1.0001 0.073 Uiso 1 calc R . . C404 C 0.6344(3) 0.8271(3) 1.0466(2) 0.0563(11) Uani 1 d . . . C405 C 0.6431(3) 0.7536(3) 1.0391(2) 0.0533(11) Uani 1 d . . . H405 H 0.6429 0.7413 1.0740 0.064 Uiso 1 calc R . . C406 C 0.6520(3) 0.6979(3) 0.9809(2) 0.0488(10) Uani 1 d . . . C407 C 0.6643(3) 0.6179(3) 0.9732(2) 0.0516(11) Uani 1 d . . . H40A H 0.6604 0.6140 1.0131 0.062 Uiso 1 calc R . . H40B H 0.6109 0.5782 0.9357 0.062 Uiso 1 calc R . . C408 C 0.7583(3) 0.6010(2) 0.9623(2) 0.0490(10) Uani 1 d . . . C409 C 0.8413(3) 0.6302(3) 1.0175(2) 0.0580(12) Uani 1 d . . . H409 H 0.8374 0.6602 1.0598 0.070 Uiso 1 calc R . . C410 C 0.9289(3) 0.6159(3) 1.0111(3) 0.0624(13) Uani 1 d . . . C411 C 0.9325(4) 0.5667(3) 0.9486(3) 0.0667(14) Uani 1 d . . . H411 H 0.9911 0.5543 0.9449 0.080 Uiso 1 calc R . . C412 C 0.8518(3) 0.5347(3) 0.8905(2) 0.0569(12) Uani 1 d . . . C413 C 0.7663(3) 0.5571(2) 0.8994(2) 0.0503(10) Uani 1 d . . . C414 C 0.6461(5) 0.8140(3) 0.8778(2) 0.0741(15) Uani 1 d . . . C420 C 0.8589(4) 0.4774(3) 0.8233(3) 0.0660(13) Uani 1 d . . . C421 C 0.7912(4) 0.3975(3) 0.8004(3) 0.0814(16) Uani 1 d . . . H42A H 0.8134 0.3775 0.8318 0.122 Uiso 1 calc R . . H42B H 0.7917 0.3615 0.7570 0.122 Uiso 1 calc R . . H42C H 0.7264 0.4035 0.7982 0.122 Uiso 1 calc R . . C422 C 0.9627(4) 0.4658(3) 0.8286(3) 0.0858(17) Uani 1 d . . . H42D H 1.0066 0.5152 0.8435 0.129 Uiso 1 calc R . . H42E H 0.9641 0.4295 0.7855 0.129 Uiso 1 calc R . . H42F H 0.9820 0.4456 0.8601 0.129 Uiso 1 calc R . . C423 C 0.8304(5) 0.5062(4) 0.7697(3) 0.0938(19) Uani 1 d . . . H42G H 0.7639 0.5096 0.7620 0.141 Uiso 1 calc R . . H42H H 0.8380 0.4699 0.7288 0.141 Uiso 1 calc R . . H42I H 0.8714 0.5569 0.7850 0.141 Uiso 1 calc R . . C415 C 0.6457(5) 0.9006(3) 0.8996(3) 0.100(2) Uani 1 d . . . H41A H 0.5858 0.9094 0.9080 0.150 Uiso 1 calc R . . H41B H 0.6519 0.9138 0.8647 0.150 Uiso 1 calc R . . H41C H 0.6991 0.9327 0.9397 0.150 Uiso 1 calc R . . C416 C 0.5541(5) 0.7637(3) 0.8184(3) 0.101(2) Uani 1 d . . . H41D H 0.5509 0.7093 0.8061 0.151 Uiso 1 calc R . . H41E H 0.5558 0.7735 0.7811 0.151 Uiso 1 calc R . . H41F H 0.4980 0.7769 0.8309 0.151 Uiso 1 calc R . . C417 C 0.7374(5) 0.8013(3) 0.8578(3) 0.095(2) Uani 1 d . . . H41G H 0.7939 0.8329 0.8959 0.143 Uiso 1 calc R . . H41H H 0.7372 0.8160 0.8228 0.143 Uiso 1 calc R . . H41I H 0.7387 0.7471 0.8421 0.143 Uiso 1 calc R . . C418 C 0.6235(4) 0.8876(3) 1.1097(2) 0.0769(15) Uani 1 d . . . H41J H 0.5834 0.8624 1.1263 0.115 Uiso 1 calc R . . H41K H 0.5939 0.9253 1.1003 0.115 Uiso 1 calc R . . H41L H 0.6863 0.9136 1.1429 0.115 Uiso 1 calc R . . C419 C 1.0199(4) 0.6535(4) 1.0707(3) 0.0962(19) Uani 1 d . . . H41M H 1.0482 0.7041 1.0761 0.144 Uiso 1 calc R . . H41N H 1.0653 0.6211 1.0638 0.144 Uiso 1 calc R . . H41O H 1.0040 0.6593 1.1102 0.144 Uiso 1 calc R . . N1S N 0.9508(9) 0.9924(9) 0.9678(6) 0.141(4) Uani 0.50 d PDU A -1 C151 C 0.9086(10) 0.9931(10) 0.9192(7) 0.121(4) Uani 0.50 d PDU A -1 C152 C 0.8639(12) 0.9889(10) 0.8560(7) 0.111(4) Uani 0.50 d PDU A -1 H15A H 0.8892 0.9544 0.8235 0.167 Uiso 0.50 calc PR A -1 H15B H 0.8773 1.0402 0.8587 0.167 Uiso 0.50 calc PR A -1 H15C H 0.7950 0.9692 0.8430 0.167 Uiso 0.50 calc PR A -1 N2S N 0.8504(15) 1.0258(13) 0.8826(10) 0.121(5) Uani 0.35 d PDU B -2 C251 C 0.8136(15) 1.0758(13) 0.9059(12) 0.120(5) Uani 0.35 d PDU B -2 C252 C 0.7374(17) 1.1083(15) 0.9272(14) 0.130(5) Uani 0.35 d PDU B -2 H25A H 0.6757 1.0734 0.8974 0.195 Uiso 0.35 calc PR B -2 H25B H 0.7409 1.1581 0.9267 0.195 Uiso 0.35 calc PR B -2 H25C H 0.7444 1.1153 0.9718 0.195 Uiso 0.35 calc PR B -2 N3S N 0.6249(9) 1.1690(8) 1.0313(8) 0.119(4) Uani 0.45 d PDU C -3 C351 C 0.5928(10) 1.1058(8) 1.0187(9) 0.124(4) Uani 0.45 d PDU C -3 C352 C 0.5468(10) 1.0353(7) 1.0147(8) 0.113(4) Uani 0.45 d PDU C -3 H35A H 0.4942 1.0074 0.9734 0.170 Uiso 0.45 calc PR C -3 H35B H 0.5220 1.0464 1.0517 0.170 Uiso 0.45 calc PR C -3 H35C H 0.5927 1.0037 1.0164 0.170 Uiso 0.45 calc PR C -3 N4S N 0.648(2) 1.1331(17) 0.9818(18) 0.108(5) Uani 0.20 d PDU D -4 C451 C 0.697(3) 1.121(2) 0.9483(19) 0.116(6) Uani 0.20 d PDU D -4 C452 C 0.783(3) 1.115(3) 0.929(2) 0.123(6) Uani 0.20 d PDU D -4 H45A H 0.8387 1.1469 0.9679 0.184 Uiso 0.20 calc PR D -4 H45B H 0.7805 1.1337 0.8962 0.184 Uiso 0.20 calc PR D -4 H45C H 0.7872 1.0618 0.9111 0.184 Uiso 0.20 calc PR D -4 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 0.0574(8) 0.0548(7) 0.0516(7) 0.0213(6) 0.0249(6) 0.0184(6) P2 0.0576(7) 0.0437(6) 0.0512(7) 0.0149(5) 0.0201(6) 0.0151(5) O1 0.0586(19) 0.0596(19) 0.0492(18) 0.0103(15) 0.0208(15) 0.0173(15) O2 0.0568(19) 0.0616(19) 0.0537(18) 0.0317(15) 0.0249(15) 0.0215(15) O3 0.077(2) 0.0478(19) 0.070(2) 0.0011(17) 0.0288(19) 0.0089(17) O4 0.120(3) 0.072(2) 0.081(3) 0.031(2) 0.044(2) -0.001(2) O5 0.058(2) 0.067(2) 0.093(3) 0.028(2) 0.0144(19) 0.0221(18) O6 0.097(3) 0.057(2) 0.136(4) 0.039(2) 0.006(3) 0.020(2) O7 0.0634(19) 0.0440(16) 0.0432(16) 0.0125(13) 0.0180(14) 0.0166(14) O8 0.065(2) 0.059(2) 0.0478(18) 0.0177(15) 0.0214(15) 0.0096(16) N1 0.090(3) 0.072(3) 0.089(3) 0.046(3) 0.052(3) 0.027(2) N2 0.142(5) 0.109(4) 0.128(5) 0.064(4) 0.086(4) 0.029(4) N3 0.302(12) 0.200(9) 0.252(10) 0.125(8) 0.221(10) 0.087(8) N4 0.048(2) 0.054(2) 0.055(2) 0.0115(18) 0.0166(18) 0.0147(18) N5 0.053(2) 0.054(2) 0.052(2) 0.0175(18) 0.0200(18) 0.0169(19) N6 0.066(3) 0.037(2) 0.063(2) 0.0092(18) 0.020(2) 0.0097(18) C101 0.055(3) 0.062(3) 0.047(3) 0.017(2) 0.022(2) 0.020(2) C102 0.068(3) 0.063(3) 0.046(3) 0.021(2) 0.015(2) 0.028(3) C103 0.082(4) 0.075(4) 0.049(3) 0.019(3) 0.027(3) 0.036(3) C104 0.074(3) 0.087(4) 0.048(3) 0.027(3) 0.031(3) 0.038(3) C105 0.077(3) 0.093(4) 0.056(3) 0.046(3) 0.029(3) 0.036(3) C106 0.064(3) 0.069(3) 0.040(2) 0.023(2) 0.018(2) 0.025(3) C107 0.066(3) 0.072(3) 0.053(3) 0.036(3) 0.021(2) 0.025(3) C108 0.064(3) 0.056(3) 0.051(3) 0.024(2) 0.026(2) 0.023(2) C109 0.079(4) 0.064(3) 0.064(3) 0.032(3) 0.035(3) 0.017(3) C110 0.063(3) 0.072(3) 0.079(4) 0.030(3) 0.029(3) 0.012(3) C111 0.061(3) 0.092(4) 0.063(3) 0.028(3) 0.019(3) 0.016(3) C112 0.057(3) 0.066(3) 0.049(3) 0.022(2) 0.021(2) 0.018(2) C113 0.056(3) 0.058(3) 0.046(3) 0.023(2) 0.023(2) 0.023(2) C114 0.085(4) 0.061(3) 0.069(3) 0.023(3) 0.032(3) 0.025(3) C115 0.153(6) 0.083(4) 0.107(5) 0.060(4) 0.037(5) 0.028(4) C116 0.143(6) 0.063(4) 0.135(6) 0.007(4) 0.067(5) 0.022(4) C117 0.080(4) 0.083(4) 0.149(6) 0.042(4) 0.033(4) 0.018(3) C118 0.111(5) 0.117(5) 0.085(4) 0.048(4) 0.062(4) 0.056(4) C119 0.105(5) 0.092(5) 0.122(6) 0.038(4) 0.042(4) -0.012(4) C120 0.071(3) 0.085(4) 0.056(3) 0.037(3) 0.020(3) 0.024(3) C121 0.136(6) 0.119(5) 0.074(4) 0.059(4) 0.047(4) 0.067(4) C122 0.103(4) 0.104(5) 0.071(4) 0.044(3) 0.051(3) 0.037(4) C123 0.112(5) 0.152(7) 0.060(4) 0.049(4) 0.000(4) -0.011(5) C124 0.062(3) 0.044(3) 0.047(3) 0.013(2) 0.021(2) 0.018(2) C125 0.062(3) 0.050(3) 0.056(3) 0.018(2) 0.018(2) 0.015(2) C126 0.101(5) 0.040(3) 0.147(6) 0.000(3) 0.042(4) 0.015(3) C127 0.056(3) 0.053(3) 0.053(3) 0.020(2) 0.021(2) 0.019(2) C128 0.072(4) 0.048(3) 0.062(3) 0.012(2) 0.017(3) 0.023(3) C129 0.083(4) 0.109(5) 0.126(6) 0.052(4) 0.024(4) 0.057(4) C201 0.054(3) 0.039(2) 0.053(3) 0.013(2) 0.021(2) 0.011(2) C202 0.070(3) 0.048(3) 0.055(3) 0.021(2) 0.022(2) 0.006(2) C203 0.081(4) 0.060(3) 0.048(3) 0.017(2) 0.026(3) 0.009(3) C204 0.064(3) 0.047(3) 0.058(3) 0.004(2) 0.026(2) 0.003(2) C205 0.058(3) 0.044(3) 0.074(3) 0.020(2) 0.023(3) 0.012(2) C206 0.050(3) 0.044(2) 0.050(3) 0.010(2) 0.019(2) 0.010(2) C207 0.069(3) 0.051(3) 0.059(3) 0.024(2) 0.022(2) 0.022(2) C208 0.068(3) 0.047(3) 0.054(3) 0.025(2) 0.018(2) 0.010(2) C209 0.080(4) 0.049(3) 0.057(3) 0.028(2) 0.016(3) 0.013(3) C210 0.066(3) 0.062(3) 0.065(3) 0.033(3) 0.019(3) 0.004(3) C211 0.066(3) 0.088(4) 0.067(3) 0.047(3) 0.028(3) 0.016(3) C212 0.067(3) 0.072(3) 0.054(3) 0.033(3) 0.023(3) 0.014(3) C213 0.059(3) 0.053(3) 0.051(3) 0.023(2) 0.012(2) 0.003(2) C214 0.121(5) 0.051(3) 0.057(3) 0.026(3) 0.033(3) 0.021(3) C215 0.188(7) 0.058(4) 0.086(4) 0.033(3) 0.044(5) -0.004(4) C216 0.179(7) 0.073(4) 0.066(4) 0.042(3) 0.047(4) 0.027(4) C217 0.177(7) 0.093(5) 0.087(4) 0.054(4) 0.052(5) 0.078(5) C218 0.087(4) 0.063(3) 0.066(3) 0.007(3) 0.033(3) 0.013(3) C219 0.087(4) 0.076(4) 0.092(4) 0.035(3) 0.023(3) -0.004(3) C220 0.081(4) 0.084(4) 0.061(3) 0.022(3) 0.037(3) 0.019(3) C221 0.168(8) 0.097(5) 0.139(7) 0.039(5) 0.089(6) 0.061(5) C222 0.171(8) 0.196(9) 0.050(4) 0.026(5) 0.035(5) 0.062(7) C223 0.138(7) 0.152(8) 0.152(8) 0.011(6) 0.101(6) -0.001(6) P3 0.0600(8) 0.0588(8) 0.0576(8) 0.0231(6) 0.0226(6) 0.0148(6) P4 0.0529(7) 0.0504(7) 0.0446(6) 0.0177(5) 0.0202(5) 0.0131(5) O9 0.0526(19) 0.062(2) 0.064(2) 0.0293(16) 0.0184(16) 0.0086(15) O10 0.058(2) 0.0560(19) 0.068(2) 0.0127(16) 0.0262(17) 0.0076(16) O11 0.077(2) 0.067(2) 0.0498(19) 0.0052(17) 0.0041(17) 0.0309(18) O12 0.118(3) 0.080(3) 0.062(2) 0.012(2) 0.004(2) 0.055(3) O13 0.070(2) 0.077(2) 0.067(2) 0.0388(19) 0.0300(19) 0.0143(18) O14 0.102(3) 0.135(4) 0.064(2) 0.061(3) 0.019(2) 0.012(3) O15 0.0604(18) 0.0449(16) 0.0414(16) 0.0130(13) 0.0232(14) 0.0091(14) O16 0.0507(18) 0.0513(17) 0.0501(18) 0.0158(14) 0.0155(15) 0.0151(14) N7 0.087(4) 0.098(4) 0.099(4) 0.062(3) 0.030(3) 0.039(3) N8 0.109(5) 0.089(4) 0.116(5) 0.053(4) 0.007(4) 0.031(4) N9 0.172(7) 0.148(7) 0.231(9) 0.108(7) 0.051(7) 0.093(6) N10 0.043(2) 0.074(3) 0.054(2) 0.017(2) 0.0217(18) 0.0077(19) N11 0.051(2) 0.063(2) 0.049(2) 0.0160(19) 0.0230(19) 0.0175(19) N12 0.051(2) 0.072(3) 0.038(2) 0.0130(18) 0.0145(17) 0.0067(19) C301 0.058(3) 0.064(3) 0.057(3) 0.029(3) 0.028(2) 0.018(2) C302 0.057(3) 0.063(3) 0.062(3) 0.025(3) 0.025(3) 0.014(2) C303 0.076(4) 0.079(4) 0.077(4) 0.032(3) 0.017(3) 0.009(3) C304 0.091(4) 0.096(5) 0.070(4) 0.041(4) 0.010(3) 0.014(4) C305 0.101(5) 0.080(4) 0.074(4) 0.043(3) 0.034(4) 0.033(4) C306 0.070(3) 0.064(3) 0.060(3) 0.028(3) 0.032(3) 0.018(3) C307 0.080(4) 0.065(3) 0.075(3) 0.040(3) 0.037(3) 0.019(3) C308 0.076(3) 0.043(3) 0.067(3) 0.026(2) 0.040(3) 0.013(2) C309 0.086(4) 0.048(3) 0.086(4) 0.035(3) 0.039(3) 0.014(3) C310 0.080(4) 0.052(3) 0.094(4) 0.033(3) 0.049(3) 0.021(3) C311 0.088(4) 0.046(3) 0.087(4) 0.016(3) 0.052(3) 0.014(3) C312 0.066(3) 0.050(3) 0.066(3) 0.024(2) 0.033(3) 0.004(2) C313 0.066(3) 0.047(3) 0.072(3) 0.023(2) 0.036(3) 0.012(2) C314 0.076(4) 0.055(3) 0.083(4) 0.024(3) 0.036(3) 0.017(3) C315 0.094(5) 0.073(4) 0.135(6) 0.027(4) 0.050(4) 0.037(3) C316 0.117(5) 0.060(4) 0.108(5) 0.023(3) 0.023(4) 0.007(3) C317 0.129(5) 0.073(4) 0.095(4) 0.048(3) 0.045(4) 0.029(4) C318 0.126(6) 0.151(7) 0.118(6) 0.069(6) -0.028(5) 0.015(5) C319 0.126(5) 0.081(4) 0.131(6) 0.052(4) 0.085(5) 0.053(4) C320 0.074(4) 0.071(4) 0.074(4) 0.024(3) 0.034(3) 0.006(3) C321 0.076(4) 0.113(5) 0.087(4) 0.040(4) 0.020(3) 0.001(4) C322 0.125(5) 0.087(4) 0.093(5) 0.048(4) 0.037(4) 0.006(4) C323 0.103(5) 0.127(6) 0.065(4) 0.012(4) 0.031(4) 0.011(4) C324 0.053(3) 0.051(3) 0.040(2) 0.016(2) 0.015(2) 0.019(2) C325 0.067(3) 0.053(3) 0.055(3) 0.015(2) 0.016(2) 0.030(3) C326 0.106(5) 0.097(5) 0.065(4) 0.002(3) -0.009(3) 0.037(4) C327 0.061(3) 0.056(3) 0.039(2) 0.020(2) 0.023(2) 0.018(2) C328 0.073(4) 0.058(3) 0.055(3) 0.024(2) 0.023(3) 0.017(3) C329 0.094(4) 0.109(5) 0.116(5) 0.073(4) 0.063(4) 0.027(4) C401 0.049(3) 0.046(2) 0.042(2) 0.012(2) 0.017(2) 0.012(2) C402 0.064(3) 0.054(3) 0.043(2) 0.015(2) 0.020(2) 0.014(2) C403 0.075(3) 0.056(3) 0.049(3) 0.019(2) 0.018(2) 0.026(2) C404 0.058(3) 0.062(3) 0.043(3) 0.016(2) 0.019(2) 0.014(2) C405 0.052(3) 0.065(3) 0.039(2) 0.020(2) 0.018(2) 0.010(2) C406 0.047(3) 0.056(3) 0.043(2) 0.022(2) 0.015(2) 0.010(2) C407 0.055(3) 0.059(3) 0.046(2) 0.028(2) 0.019(2) 0.009(2) C408 0.051(3) 0.050(3) 0.056(3) 0.032(2) 0.019(2) 0.011(2) C409 0.066(3) 0.062(3) 0.056(3) 0.036(2) 0.020(2) 0.012(2) C410 0.052(3) 0.075(3) 0.071(3) 0.048(3) 0.014(3) 0.009(2) C411 0.054(3) 0.071(3) 0.095(4) 0.055(3) 0.026(3) 0.020(3) C412 0.060(3) 0.050(3) 0.077(3) 0.038(3) 0.030(3) 0.017(2) C413 0.052(3) 0.048(2) 0.058(3) 0.030(2) 0.022(2) 0.012(2) C414 0.124(5) 0.049(3) 0.053(3) 0.022(2) 0.035(3) 0.029(3) C420 0.074(3) 0.060(3) 0.077(3) 0.033(3) 0.034(3) 0.032(3) C421 0.080(4) 0.066(3) 0.087(4) 0.024(3) 0.025(3) 0.024(3) C422 0.078(4) 0.090(4) 0.110(5) 0.049(4) 0.052(4) 0.036(3) C423 0.134(5) 0.111(5) 0.082(4) 0.061(4) 0.061(4) 0.068(4) C415 0.177(7) 0.064(4) 0.072(4) 0.034(3) 0.051(4) 0.040(4) C416 0.154(6) 0.078(4) 0.055(3) 0.027(3) 0.012(4) 0.030(4) C417 0.149(6) 0.072(4) 0.101(5) 0.049(4) 0.079(4) 0.033(4) C418 0.093(4) 0.079(4) 0.051(3) 0.018(3) 0.029(3) 0.026(3) C419 0.068(4) 0.137(6) 0.089(4) 0.070(4) 0.006(3) 0.008(4) N1S 0.119(9) 0.174(9) 0.118(9) 0.063(8) 0.040(6) 0.006(7) C151 0.100(7) 0.137(8) 0.122(8) 0.065(7) 0.036(6) -0.007(6) C152 0.097(7) 0.113(9) 0.123(9) 0.061(8) 0.031(6) -0.002(7) N2S 0.101(7) 0.129(9) 0.121(9) 0.065(7) 0.017(6) -0.011(7) C251 0.102(9) 0.109(9) 0.121(9) 0.061(8) -0.015(7) -0.001(7) C252 0.112(10) 0.099(8) 0.131(9) 0.047(7) -0.022(8) -0.002(8) N3S 0.095(7) 0.103(7) 0.149(9) 0.074(7) -0.007(6) 0.014(6) C351 0.090(7) 0.105(7) 0.143(8) 0.045(8) -0.006(6) 0.037(6) C352 0.091(8) 0.104(8) 0.128(9) 0.039(8) 0.023(7) 0.045(6) N4S 0.092(8) 0.079(8) 0.138(9) 0.065(8) -0.016(7) 0.013(7) C451 0.100(10) 0.084(8) 0.132(10) 0.053(8) -0.017(7) 0.002(8) C452 0.103(10) 0.097(9) 0.126(10) 0.047(8) -0.019(8) 0.000(9) _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 O2 1.538(3) . ? P1 N4 1.541(4) . ? P1 O1 1.563(3) . ? P1 N1 1.664(4) . ? P2 O7 1.583(3) . ? P2 O8 1.586(3) . ? P2 N6 1.599(4) . ? P2 C127 1.720(5) . ? O1 C101 1.429(5) . ? O2 C113 1.429(5) . ? O3 C125 1.313(5) . ? O3 C126 1.465(6) . ? O4 C125 1.188(5) . ? O5 C128 1.331(6) . ? O5 C129 1.450(6) . ? O6 C128 1.225(6) . ? O7 C201 1.401(5) . ? O8 C213 1.412(5) . ? N1 N2 1.192(6) . ? N2 N3 1.117(7) . ? N4 N5 1.394(5) . ? N5 C124 1.312(5) . ? N5 N6 1.387(5) . ? C101 C106 1.378(6) . ? C101 C102 1.401(6) . ? C102 C103 1.399(6) . ? C102 C114 1.536(7) . ? C103 C104 1.381(7) . ? C104 C105 1.361(7) . ? C104 C118 1.517(6) . ? C105 C106 1.401(6) . ? C106 C107 1.508(6) . ? C107 C108 1.509(6) . ? C108 C109 1.380(6) . ? C108 C113 1.381(6) . ? C109 C110 1.376(7) . ? C110 C111 1.390(7) . ? C110 C119 1.515(7) . ? C111 C112 1.380(7) . ? C112 C113 1.395(6) . ? C112 C120 1.549(6) . ? C114 C115 1.503(8) . ? C114 C117 1.533(7) . ? C114 C116 1.538(7) . ? C120 C122 1.519(7) . ? C120 C121 1.530(7) . ? C120 C123 1.533(7) . ? C124 C127 1.412(6) . ? C124 C125 1.496(6) . ? C127 C128 1.424(6) . ? C201 C206 1.382(6) . ? C201 C202 1.395(6) . ? C202 C203 1.391(6) . ? C202 C214 1.520(7) . ? C203 C204 1.390(7) . ? C204 C205 1.369(7) . ? C204 C218 1.491(6) . ? C205 C206 1.401(6) . ? C206 C207 1.508(6) . ? C207 C208 1.503(6) . ? C208 C209 1.375(6) . ? C208 C213 1.382(6) . ? C209 C210 1.378(7) . ? C210 C211 1.371(7) . ? C210 C219 1.510(7) . ? C211 C212 1.402(7) . ? C212 C213 1.393(6) . ? C212 C220 1.523(7) . ? C214 C215 1.536(8) . ? C214 C217 1.541(8) . ? C214 C216 1.548(7) . ? C220 C222 1.493(8) . ? C220 C221 1.514(9) . ? C220 C223 1.534(8) . ? P3 N10 1.544(4) . ? P3 O9 1.546(3) . ? P3 O10 1.547(3) . ? P3 N7 1.676(5) . ? P4 O15 1.581(3) . ? P4 O16 1.584(3) . ? P4 N12 1.612(4) . ? P4 C327 1.712(4) . ? O9 C301 1.419(5) . ? O10 C313 1.421(5) . ? O11 C325 1.307(5) . ? O11 C326 1.453(6) . ? O12 C325 1.189(5) . ? O13 C328 1.334(6) . ? O13 C329 1.448(5) . ? O14 C328 1.198(6) . ? O15 C401 1.395(5) . ? O16 C413 1.407(5) . ? N7 N8 1.196(7) . ? N8 N9 1.166(8) . ? N10 N11 1.390(5) . ? N11 C324 1.313(5) . ? N11 N12 1.389(5) . ? C301 C306 1.385(6) . ? C301 C302 1.387(6) . ? C302 C303 1.401(7) . ? C302 C314 1.530(7) . ? C303 C304 1.380(8) . ? C304 C305 1.388(8) . ? C304 C318 1.521(8) . ? C305 C306 1.375(7) . ? C306 C307 1.522(7) . ? C307 C308 1.515(6) . ? C308 C313 1.387(7) . ? C308 C309 1.389(6) . ? C309 C310 1.376(7) . ? C310 C311 1.382(8) . ? C310 C319 1.501(7) . ? C311 C312 1.394(7) . ? C312 C313 1.404(6) . ? C312 C320 1.536(7) . ? C314 C315 1.525(7) . ? C314 C317 1.527(7) . ? C314 C316 1.539(7) . ? C320 C322 1.525(8) . ? C320 C321 1.529(7) . ? C320 C323 1.539(7) . ? C324 C327 1.409(6) . ? C324 C325 1.471(6) . ? C327 C328 1.458(6) . ? C401 C402 1.388(6) . ? C401 C406 1.391(6) . ? C402 C403 1.405(6) . ? C402 C414 1.542(6) . ? C403 C404 1.381(6) . ? C404 C405 1.380(6) . ? C404 C418 1.507(6) . ? C405 C406 1.381(6) . ? C406 C407 1.515(6) . ? C407 C408 1.505(6) . ? C408 C409 1.388(6) . ? C408 C413 1.392(6) . ? C409 C410 1.369(6) . ? C410 C411 1.383(7) . ? C410 C419 1.506(7) . ? C411 C412 1.402(7) . ? C412 C413 1.402(6) . ? C412 C420 1.528(7) . ? C414 C417 1.527(7) . ? C414 C416 1.534(8) . ? C414 C415 1.535(7) . ? C420 C421 1.539(7) . ? C420 C422 1.541(7) . ? C420 C423 1.544(7) . ? N1S C151 1.151(9) . ? C151 C152 1.413(10) . ? N2S C251 1.156(9) . ? C251 C252 1.432(10) . ? N3S C351 1.140(9) . ? C351 C352 1.405(9) . ? N4S C451 1.147(10) . ? C451 C452 1.433(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 N4 108.94(19) . . ? O2 P1 O1 105.87(16) . . ? N4 P1 O1 120.8(2) . . ? O2 P1 N1 101.1(2) . . ? N4 P1 N1 119.0(2) . . ? O1 P1 N1 98.8(2) . . ? O7 P2 O8 100.31(17) . . ? O7 P2 N6 118.03(18) . . ? O8 P2 N6 111.32(19) . . ? O7 P2 C127 111.82(19) . . ? O8 P2 C127 117.77(19) . . ? N6 P2 C127 98.6(2) . . ? C101 O1 P1 127.8(3) . . ? C113 O2 P1 131.1(3) . . ? C125 O3 C126 117.6(4) . . ? C128 O5 C129 116.8(4) . . ? C201 O7 P2 129.0(3) . . ? C213 O8 P2 128.4(3) . . ? N2 N1 P1 121.8(4) . . ? N3 N2 N1 176.3(8) . . ? N5 N4 P1 120.4(3) . . ? C124 N5 N6 116.9(4) . . ? C124 N5 N4 124.5(4) . . ? N6 N5 N4 117.8(3) . . ? N5 N6 P2 106.7(3) . . ? C106 C101 C102 123.7(4) . . ? C106 C101 O1 118.7(4) . . ? C102 C101 O1 117.5(4) . . ? C103 C102 C101 114.5(5) . . ? C103 C102 C114 120.5(4) . . ? C101 C102 C114 124.9(4) . . ? C104 C103 C102 124.1(5) . . ? C105 C104 C103 118.3(4) . . ? C105 C104 C118 121.0(5) . . ? C103 C104 C118 120.8(5) . . ? C104 C105 C106 121.6(5) . . ? C101 C106 C105 117.8(4) . . ? C101 C106 C107 123.5(4) . . ? C105 C106 C107 118.7(5) . . ? C106 C107 C108 113.5(4) . . ? C109 C108 C113 117.7(4) . . ? C109 C108 C107 119.5(4) . . ? C113 C108 C107 122.8(4) . . ? C110 C109 C108 121.7(5) . . ? C109 C110 C111 118.2(5) . . ? C109 C110 C119 120.4(5) . . ? C111 C110 C119 121.3(5) . . ? C112 C111 C110 123.2(5) . . ? C111 C112 C113 115.6(4) . . ? C111 C112 C120 121.1(4) . . ? C113 C112 C120 123.2(4) . . ? C108 C113 C112 123.7(4) . . ? C108 C113 O2 119.0(4) . . ? C112 C113 O2 117.3(4) . . ? C115 C114 C117 110.2(5) . . ? C115 C114 C102 109.0(4) . . ? C117 C114 C102 110.9(4) . . ? C115 C114 C116 108.1(5) . . ? C117 C114 C116 106.9(5) . . ? C102 C114 C116 111.7(5) . . ? C122 C120 C121 110.2(5) . . ? C122 C120 C123 107.2(5) . . ? C121 C120 C123 107.2(5) . . ? C122 C120 C112 110.3(4) . . ? C121 C120 C112 110.5(4) . . ? C123 C120 C112 111.4(5) . . ? N5 C124 C127 114.0(4) . . ? N5 C124 C125 121.6(4) . . ? C127 C124 C125 124.3(4) . . ? O4 C125 O3 124.7(5) . . ? O4 C125 C124 125.0(4) . . ? O3 C125 C124 110.2(4) . . ? C124 C127 C128 122.9(4) . . ? C124 C127 P2 103.6(3) . . ? C128 C127 P2 131.8(4) . . ? O6 C128 O5 121.1(5) . . ? O6 C128 C127 125.7(5) . . ? O5 C128 C127 113.2(4) . . ? C206 C201 C202 123.8(4) . . ? C206 C201 O7 117.0(4) . . ? C202 C201 O7 118.8(4) . . ? C203 C202 C201 114.5(4) . . ? C203 C202 C214 122.3(4) . . ? C201 C202 C214 123.2(4) . . ? C204 C203 C202 124.7(4) . . ? C205 C204 C203 117.4(4) . . ? C205 C204 C218 122.2(5) . . ? C203 C204 C218 120.4(5) . . ? C204 C205 C206 121.5(4) . . ? C201 C206 C205 118.0(4) . . ? C201 C206 C207 121.5(4) . . ? C205 C206 C207 120.6(4) . . ? C208 C207 C206 112.9(4) . . ? C209 C208 C213 117.1(4) . . ? C209 C208 C207 118.9(4) . . ? C213 C208 C207 124.0(4) . . ? C208 C209 C210 122.6(5) . . ? C211 C210 C209 117.7(5) . . ? C211 C210 C219 121.9(5) . . ? C209 C210 C219 120.3(5) . . ? C210 C211 C212 123.2(5) . . ? C213 C212 C211 115.1(5) . . ? C213 C212 C220 125.7(5) . . ? C211 C212 C220 119.1(4) . . ? C208 C213 C212 123.7(4) . . ? C208 C213 O8 119.0(4) . . ? C212 C213 O8 117.2(4) . . ? C202 C214 C215 109.3(5) . . ? C202 C214 C217 110.7(4) . . ? C215 C214 C217 111.4(5) . . ? C202 C214 C216 111.2(4) . . ? C215 C214 C216 107.5(5) . . ? C217 C214 C216 106.8(5) . . ? C222 C220 C221 109.8(6) . . ? C222 C220 C212 110.2(5) . . ? C221 C220 C212 111.0(4) . . ? C222 C220 C223 108.8(6) . . ? C221 C220 C223 105.0(6) . . ? C212 C220 C223 111.8(5) . . ? N10 P3 O9 108.7(2) . . ? N10 P3 O10 120.3(2) . . ? O9 P3 O10 107.13(18) . . ? N10 P3 N7 117.9(2) . . ? O9 P3 N7 100.8(2) . . ? O10 P3 N7 99.9(2) . . ? O15 P4 O16 101.14(16) . . ? O15 P4 N12 117.54(17) . . ? O16 P4 N12 111.00(19) . . ? O15 P4 C327 112.13(19) . . ? O16 P4 C327 117.51(18) . . ? N12 P4 C327 98.4(2) . . ? C301 O9 P3 131.4(3) . . ? C313 O10 P3 128.7(3) . . ? C325 O11 C326 117.3(4) . . ? C328 O13 C329 116.2(4) . . ? C401 O15 P4 129.5(3) . . ? C413 O16 P4 128.0(3) . . ? N8 N7 P3 119.8(5) . . ? N9 N8 N7 176.6(8) . . ? N11 N10 P3 120.0(3) . . ? C324 N11 N12 118.1(4) . . ? C324 N11 N10 122.3(4) . . ? N12 N11 N10 118.9(3) . . ? N11 N12 P4 105.8(3) . . ? C306 C301 C302 125.2(5) . . ? C306 C301 O9 118.8(4) . . ? C302 C301 O9 115.8(4) . . ? C301 C302 C303 114.4(5) . . ? C301 C302 C314 124.5(5) . . ? C303 C302 C314 121.0(5) . . ? C304 C303 C302 123.1(5) . . ? C303 C304 C305 118.8(5) . . ? C303 C304 C318 120.2(6) . . ? C305 C304 C318 121.0(6) . . ? C306 C305 C304 121.3(5) . . ? C305 C306 C301 117.2(5) . . ? C305 C306 C307 119.7(5) . . ? C301 C306 C307 123.1(5) . . ? C308 C307 C306 113.6(4) . . ? C313 C308 C309 118.7(4) . . ? C313 C308 C307 122.7(4) . . ? C309 C308 C307 118.6(5) . . ? C310 C309 C308 121.4(5) . . ? C309 C310 C311 117.6(5) . . ? C309 C310 C319 121.3(6) . . ? C311 C310 C319 121.1(5) . . ? C310 C311 C312 124.7(5) . . ? C311 C312 C313 114.8(5) . . ? C311 C312 C320 121.7(5) . . ? C313 C312 C320 123.4(4) . . ? C308 C313 C312 122.7(4) . . ? C308 C313 O10 119.4(4) . . ? C312 C313 O10 117.7(5) . . ? C315 C314 C317 111.8(5) . . ? C315 C314 C302 109.2(4) . . ? C317 C314 C302 111.2(4) . . ? C315 C314 C316 106.8(5) . . ? C317 C314 C316 105.8(5) . . ? C302 C314 C316 111.9(5) . . ? C322 C320 C321 109.7(5) . . ? C322 C320 C312 109.1(5) . . ? C321 C320 C312 113.4(4) . . ? C322 C320 C323 107.5(5) . . ? C321 C320 C323 105.8(5) . . ? C312 C320 C323 111.3(5) . . ? N11 C324 C327 113.0(4) . . ? N11 C324 C325 119.6(4) . . ? C327 C324 C325 127.5(4) . . ? O12 C325 O11 125.5(4) . . ? O12 C325 C324 123.8(4) . . ? O11 C325 C324 110.7(4) . . ? C324 C327 C328 121.7(4) . . ? C324 C327 P4 104.7(3) . . ? C328 C327 P4 132.1(4) . . ? O14 C328 O13 123.8(5) . . ? O14 C328 C327 124.2(5) . . ? O13 C328 C327 112.0(4) . . ? C402 C401 C406 123.5(4) . . ? C402 C401 O15 118.8(4) . . ? C406 C401 O15 117.5(4) . . ? C401 C402 C403 115.5(4) . . ? C401 C402 C414 123.7(4) . . ? C403 C402 C414 120.8(4) . . ? C404 C403 C402 122.9(4) . . ? C405 C404 C403 118.5(4) . . ? C405 C404 C418 121.6(4) . . ? C403 C404 C418 119.9(4) . . ? C404 C405 C406 121.6(4) . . ? C405 C406 C401 117.9(4) . . ? C405 C406 C407 121.7(4) . . ? C401 C406 C407 120.4(4) . . ? C408 C407 C406 114.1(3) . . ? C409 C408 C413 118.2(4) . . ? C409 C408 C407 118.6(4) . . ? C413 C408 C407 123.2(4) . . ? C410 C409 C408 121.6(5) . . ? C409 C410 C411 118.6(5) . . ? C409 C410 C419 120.9(5) . . ? C411 C410 C419 120.5(5) . . ? C410 C411 C412 123.1(5) . . ? C413 C412 C411 115.5(4) . . ? C413 C412 C420 123.8(4) . . ? C411 C412 C420 120.7(4) . . ? C408 C413 C412 122.6(4) . . ? C408 C413 O16 119.0(4) . . ? C412 C413 O16 118.2(4) . . ? C417 C414 C416 111.2(5) . . ? C417 C414 C415 107.3(5) . . ? C416 C414 C415 108.4(5) . . ? C417 C414 C402 110.6(4) . . ? C416 C414 C402 107.7(4) . . ? C415 C414 C402 111.7(4) . . ? C412 C420 C421 108.2(4) . . ? C412 C420 C422 112.1(4) . . ? C421 C420 C422 107.9(4) . . ? C412 C420 C423 111.7(4) . . ? C421 C420 C423 109.9(5) . . ? C422 C420 C423 106.9(4) . . ? N1S C151 C152 173(2) . . ? N2S C251 C252 155(2) . . ? N3S C351 C352 168(2) . . ? N4S C451 C452 159(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.425 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.063 #===END data_compound_4 _database_code_CSD 157569 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Sudha Kumaraswamy' 'Praveen Kommana' 'N. Satish Kumar' 'K. C. Kumara Swamy' _publ_contact_author_name 'Dr K. C. Kumara Swamy' _publ_contact_author_address ; Dr K. C. Kumara Swamy School of Chemistry University of Hyderabad Gachibowli Hyderabad A. P. 500046 INDIA ; _publ_contact_author_email 'KCKSSC@UOHYD.ERNET.IN' _publ_section_title ; Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 N O7 P' _chemical_formula_weight 553.57 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 P21/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 10.308(3) _cell_length_b 17.604(4) _cell_length_c 16.464(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.14(2) _cell_angle_gamma 90.00 _cell_volume 2854.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5298 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.95 _reflns_number_total 5012 _reflns_number_gt 3228 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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 w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.7507P] 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 5012 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.04124(7) 0.00623(4) 0.28929(4) 0.0397(2) Uani 1 d . . . O1 O 0.13337(16) 0.07435(9) 0.32703(10) 0.0397(4) Uani 1 d . . . O2 O -0.10764(17) 0.03444(10) 0.26539(11) 0.0458(4) Uani 1 d . . . O3 O 0.1505(3) -0.00507(16) 0.07477(16) 0.1049(10) Uani 1 d . . . O4 O 0.0934(2) 0.09371(12) 0.13924(12) 0.0615(5) Uani 1 d . . . O5 O 0.0980(2) -0.18193(13) 0.10260(14) 0.0721(6) Uani 1 d . . . O6 O 0.3028(2) -0.15098(13) 0.18403(13) 0.0669(6) Uani 1 d . . . O7 O 0.1346(3) -0.18822(11) 0.32030(14) 0.0747(7) Uani 1 d . . . N N 0.0609(2) -0.06907(12) 0.34130(13) 0.0461(5) Uani 1 d . . . C1 C 0.2023(2) 0.09330(13) 0.41215(14) 0.0386(5) Uani 1 d . . . C2 C 0.3393(2) 0.10761(14) 0.43353(16) 0.0421(6) Uani 1 d . . . C3 C 0.3959(3) 0.13347(16) 0.51503(17) 0.0521(7) Uani 1 d . . . H3 H 0.4877 0.1460 0.5319 0.063 Uiso 1 calc R . . C4 C 0.3246(3) 0.14183(16) 0.57296(16) 0.0513(7) Uani 1 d . . . C5 C 0.1897(3) 0.12441(16) 0.54825(16) 0.0492(6) Uani 1 d . . . H5 H 0.1406 0.1287 0.5872 0.059 Uiso 1 calc R . . C6 C 0.1250(2) 0.10073(14) 0.46715(15) 0.0405(6) Uani 1 d . . . C7 C -0.0229(2) 0.08262(14) 0.43941(15) 0.0417(6) Uani 1 d . . . H7A H -0.0572 0.0882 0.4880 0.050 Uiso 1 calc R . . H7B H -0.0338 0.0298 0.4221 0.050 Uiso 1 calc R . . C8 C -0.1085(2) 0.12989(14) 0.36836(15) 0.0403(6) Uani 1 d . . . C9 C -0.1501(2) 0.20064(14) 0.38605(17) 0.0444(6) Uani 1 d . . . H9 H -0.1154 0.2203 0.4406 0.053 Uiso 1 calc R . . C10 C -0.2408(3) 0.24265(15) 0.32593(18) 0.0474(6) Uani 1 d . . . C11 C -0.2965(3) 0.21043(15) 0.24728(18) 0.0491(6) Uani 1 d . . . H11 H -0.3637 0.2373 0.2076 0.059 Uiso 1 calc R . . C12 C -0.2586(3) 0.14082(15) 0.22373(16) 0.0452(6) Uani 1 d . . . C13 C -0.1569(2) 0.10429(14) 0.28601(15) 0.0399(5) Uani 1 d . . . C14 C 0.4260(3) 0.09464(15) 0.37400(17) 0.0483(6) Uani 1 d . . . C15 C 0.4153(3) 0.01209(17) 0.3463(2) 0.0641(8) Uani 1 d . . . H15A H 0.4357 -0.0201 0.3955 0.096 Uiso 1 calc R . . H15B H 0.4787 0.0023 0.3150 0.096 Uiso 1 calc R . . H15C H 0.3249 0.0019 0.3109 0.096 Uiso 1 calc R . . C16 C 0.5742(3) 0.1106(2) 0.4176(2) 0.0804(11) Uani 1 d . . . H16A H 0.6068 0.0770 0.4651 0.121 Uiso 1 calc R . . H16B H 0.5847 0.1623 0.4371 0.121 Uiso 1 calc R . . H16C H 0.6255 0.1028 0.3781 0.121 Uiso 1 calc R . . C17 C 0.3800(4) 0.14583(18) 0.2971(2) 0.0677(9) Uani 1 d . . . H17A H 0.4307 0.1342 0.2582 0.102 Uiso 1 calc R . . H17B H 0.3952 0.1979 0.3147 0.102 Uiso 1 calc R . . H17C H 0.2850 0.1379 0.2695 0.102 Uiso 1 calc R . . C18 C 0.3968(3) 0.1684(2) 0.6613(2) 0.0775(10) Uani 1 d . . . H18A H 0.3890 0.2226 0.6642 0.116 Uiso 1 calc R . . H18B H 0.4910 0.1546 0.6755 0.116 Uiso 1 calc R . . H18C H 0.3567 0.1450 0.7008 0.116 Uiso 1 calc R . . C19 C -0.2848(3) 0.31921(17) 0.3464(2) 0.0714(9) Uani 1 d . . . H19A H -0.3068 0.3504 0.2963 0.107 Uiso 1 calc R . . H19B H -0.2126 0.3424 0.3900 0.107 Uiso 1 calc R . . H19C H -0.3633 0.3141 0.3660 0.107 Uiso 1 calc R . . C20 C -0.3310(3) 0.10522(19) 0.13779(17) 0.0572(7) Uani 1 d . . . C21 C -0.2341(4) 0.0907(3) 0.0861(2) 0.0938(13) Uani 1 d . . . H21A H -0.1686 0.0531 0.1140 0.141 Uiso 1 calc R . . H21B H -0.1881 0.1370 0.0807 0.141 Uiso 1 calc R . . H21C H -0.2840 0.0728 0.0306 0.141 Uiso 1 calc R . . C22 C -0.4424(3) 0.1570(2) 0.0856(2) 0.0787(10) Uani 1 d . . . H22A H -0.4873 0.1330 0.0323 0.118 Uiso 1 calc R . . H22B H -0.4035 0.2042 0.0753 0.118 Uiso 1 calc R . . H22C H -0.5071 0.1664 0.1161 0.118 Uiso 1 calc R . . C23 C -0.3964(4) 0.0315(2) 0.1518(2) 0.0797(10) Uani 1 d . . . H23A H -0.3287 -0.0015 0.1870 0.120 Uiso 1 calc R . . H23B H -0.4372 0.0073 0.0980 0.120 Uiso 1 calc R . . H23C H -0.4649 0.0417 0.1791 0.120 Uiso 1 calc R . . C24 C 0.0881(2) -0.02315(15) 0.19881(15) 0.0420(6) Uani 1 d . . . C25 C 0.1209(3) -0.09537(15) 0.21421(16) 0.0438(6) Uani 1 d . . . C26 C 0.1068(3) -0.12381(15) 0.29839(17) 0.0487(6) Uani 1 d . . . C27 C 0.1128(3) 0.02158(18) 0.12955(17) 0.0535(7) Uani 1 d . . . C28 C 0.1244(4) 0.1451(2) 0.0795(2) 0.0935(13) Uani 1 d . . . H28A H 0.2124 0.1334 0.0741 0.140 Uiso 1 calc R . . H28B H 0.1240 0.1964 0.0994 0.140 Uiso 1 calc R . . H28C H 0.0574 0.1400 0.0252 0.140 Uiso 1 calc R . . C29 C 0.1708(3) -0.14755(16) 0.15886(17) 0.0512(7) Uani 1 d . . . C30 C 0.3630(4) -0.2024(2) 0.1373(2) 0.0807(11) Uani 1 d . . . H30A H 0.3782 -0.2508 0.1655 0.121 Uiso 1 calc R . . H30B H 0.4480 -0.1821 0.1345 0.121 Uiso 1 calc R . . H30C H 0.3030 -0.2087 0.0808 0.121 Uiso 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 0.0421(4) 0.0417(4) 0.0395(4) 0.0002(3) 0.0183(3) 0.0031(3) O1 0.0427(9) 0.0435(9) 0.0369(9) -0.0008(7) 0.0176(7) -0.0027(7) O2 0.0384(9) 0.0498(10) 0.0517(10) -0.0042(8) 0.0169(8) 0.0074(8) O3 0.170(3) 0.100(2) 0.0788(17) 0.0095(14) 0.0890(19) 0.0303(18) O4 0.0781(14) 0.0596(13) 0.0533(11) 0.0134(9) 0.0294(10) 0.0025(11) O5 0.0649(14) 0.0774(15) 0.0663(13) -0.0303(12) 0.0072(11) 0.0060(11) O6 0.0514(12) 0.0815(15) 0.0670(13) -0.0289(11) 0.0160(10) 0.0119(10) O7 0.1078(19) 0.0445(12) 0.0756(15) 0.0070(10) 0.0327(13) 0.0137(12) N 0.0546(13) 0.0432(12) 0.0463(12) 0.0037(9) 0.0237(10) 0.0038(10) C1 0.0433(14) 0.0386(13) 0.0363(12) -0.0004(10) 0.0152(11) 0.0003(11) C2 0.0400(14) 0.0428(13) 0.0469(14) 0.0017(11) 0.0182(11) 0.0013(11) C3 0.0451(15) 0.0568(16) 0.0540(16) -0.0074(13) 0.0142(13) 0.0013(13) C4 0.0516(16) 0.0580(17) 0.0424(14) -0.0078(12) 0.0111(12) 0.0096(13) C5 0.0514(16) 0.0587(16) 0.0404(14) -0.0010(12) 0.0180(12) 0.0109(13) C6 0.0418(14) 0.0431(13) 0.0399(13) 0.0044(10) 0.0173(11) 0.0060(11) C7 0.0420(14) 0.0493(14) 0.0389(13) 0.0038(11) 0.0198(11) 0.0008(11) C8 0.0369(13) 0.0426(14) 0.0476(14) 0.0025(11) 0.0221(11) -0.0002(10) C9 0.0383(14) 0.0469(14) 0.0535(15) -0.0034(12) 0.0222(12) -0.0036(11) C10 0.0403(14) 0.0433(14) 0.0639(17) 0.0034(12) 0.0237(13) 0.0030(11) C11 0.0396(14) 0.0518(15) 0.0587(16) 0.0108(13) 0.0190(13) 0.0063(12) C12 0.0413(14) 0.0525(15) 0.0466(14) 0.0060(12) 0.0205(12) 0.0032(12) C13 0.0373(13) 0.0414(13) 0.0462(14) 0.0021(11) 0.0205(11) 0.0018(11) C14 0.0439(15) 0.0524(15) 0.0563(16) 0.0020(12) 0.0265(13) -0.0011(12) C15 0.0604(19) 0.0564(18) 0.088(2) -0.0021(16) 0.0417(17) 0.0075(15) C16 0.0470(18) 0.116(3) 0.087(2) -0.015(2) 0.0333(17) -0.0183(19) C17 0.082(2) 0.066(2) 0.070(2) 0.0140(16) 0.0467(18) 0.0044(17) C18 0.065(2) 0.105(3) 0.0567(18) -0.0270(18) 0.0081(16) 0.0134(19) C19 0.066(2) 0.0541(18) 0.095(2) -0.0015(17) 0.0244(18) 0.0131(15) C20 0.0489(16) 0.077(2) 0.0476(16) -0.0016(14) 0.0175(13) 0.0087(15) C21 0.072(2) 0.165(4) 0.0479(18) -0.010(2) 0.0237(17) 0.030(2) C22 0.065(2) 0.108(3) 0.0563(18) 0.0027(19) 0.0076(16) 0.024(2) C23 0.073(2) 0.080(2) 0.075(2) -0.0191(19) 0.0055(18) -0.0082(19) C24 0.0395(13) 0.0479(15) 0.0403(13) -0.0006(11) 0.0143(11) 0.0047(11) C25 0.0398(14) 0.0466(15) 0.0452(14) -0.0080(11) 0.0130(11) 0.0028(11) C26 0.0537(16) 0.0401(15) 0.0531(15) 0.0014(12) 0.0167(13) 0.0014(12) C27 0.0563(17) 0.0650(19) 0.0429(15) 0.0022(13) 0.0203(13) 0.0080(14) C28 0.119(3) 0.089(3) 0.079(2) 0.038(2) 0.038(2) -0.005(2) C29 0.0516(17) 0.0541(16) 0.0473(15) -0.0069(13) 0.0137(13) 0.0093(13) C30 0.071(2) 0.098(3) 0.081(2) -0.023(2) 0.0344(19) 0.030(2) _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 O1 1.5421(17) . ? P O2 1.5494(18) . ? P N 1.558(2) . ? P C24 1.773(2) . ? O1 C1 1.412(3) . ? O2 C13 1.410(3) . ? O3 C27 1.180(3) . ? O4 C27 1.302(3) . ? O4 C28 1.440(4) . ? O5 C29 1.174(3) . ? O6 C29 1.302(3) . ? O6 C30 1.442(3) . ? O7 C26 1.199(3) . ? N C26 1.359(3) . ? C1 C2 1.375(3) . ? C1 C6 1.377(3) . ? C2 C3 1.374(4) . ? C2 C14 1.525(3) . ? C3 C4 1.373(4) . ? C4 C5 1.364(4) . ? C4 C18 1.501(4) . ? C5 C6 1.370(3) . ? C6 C7 1.491(3) . ? C7 C8 1.494(3) . ? C8 C13 1.375(3) . ? C8 C9 1.376(3) . ? C9 C10 1.362(4) . ? C10 C11 1.375(4) . ? C10 C19 1.492(4) . ? C11 C12 1.376(4) . ? C12 C13 1.390(3) . ? C12 C20 1.526(4) . ? C14 C16 1.511(4) . ? C14 C17 1.512(4) . ? C14 C15 1.517(4) . ? C20 C23 1.511(5) . ? C20 C21 1.513(4) . ? C20 C22 1.519(4) . ? C24 C25 1.321(4) . ? C24 C27 1.469(4) . ? C25 C29 1.488(3) . ? C25 C26 1.521(4) . ? 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 P O2 107.42(10) . . ? O1 P N 118.36(11) . . ? O2 P N 111.78(11) . . ? O1 P C24 106.12(11) . . ? O2 P C24 111.99(11) . . ? N P C24 100.94(11) . . ? C1 O1 P 130.82(15) . . ? C13 O2 P 128.21(16) . . ? C27 O4 C28 117.2(3) . . ? C29 O6 C30 115.7(2) . . ? C26 N P 109.06(17) . . ? C2 C1 C6 124.3(2) . . ? C2 C1 O1 118.4(2) . . ? C6 C1 O1 117.1(2) . . ? C3 C2 C1 114.8(2) . . ? C3 C2 C14 121.1(2) . . ? C1 C2 C14 124.1(2) . . ? C4 C3 C2 123.6(3) . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C18 122.0(3) . . ? C3 C4 C18 119.5(3) . . ? C4 C5 C6 121.3(2) . . ? C5 C6 C1 117.4(2) . . ? C5 C6 C7 121.6(2) . . ? C1 C6 C7 121.0(2) . . ? C6 C7 C8 115.8(2) . . ? C13 C8 C9 117.4(2) . . ? C13 C8 C7 123.3(2) . . ? C9 C8 C7 119.2(2) . . ? C10 C9 C8 121.9(3) . . ? C9 C10 C11 117.8(2) . . ? C9 C10 C19 121.0(3) . . ? C11 C10 C19 121.0(3) . . ? C10 C11 C12 124.0(3) . . ? C11 C12 C13 114.8(2) . . ? C11 C12 C20 121.7(2) . . ? C13 C12 C20 123.4(2) . . ? C8 C13 C12 123.5(2) . . ? C8 C13 O2 118.1(2) . . ? C12 C13 O2 118.2(2) . . ? C16 C14 C17 108.1(3) . . ? C16 C14 C15 107.1(3) . . ? C17 C14 C15 110.0(3) . . ? C16 C14 C2 111.7(2) . . ? C17 C14 C2 110.5(2) . . ? C15 C14 C2 109.4(2) . . ? C23 C20 C21 109.8(3) . . ? C23 C20 C22 107.7(3) . . ? C21 C20 C22 107.3(3) . . ? C23 C20 C12 109.3(2) . . ? C21 C20 C12 111.6(3) . . ? C22 C20 C12 111.1(3) . . ? C25 C24 C27 124.9(2) . . ? C25 C24 P 103.74(19) . . ? C27 C24 P 130.4(2) . . ? C24 C25 C29 126.3(2) . . ? C24 C25 C26 113.8(2) . . ? C29 C25 C26 119.9(2) . . ? O7 C26 N 127.1(3) . . ? O7 C26 C25 120.5(2) . . ? N C26 C25 112.4(2) . . ? O3 C27 O4 125.3(3) . . ? O3 C27 C24 123.5(3) . . ? O4 C27 C24 111.1(2) . . ? O5 C29 O6 126.3(3) . . ? O5 C29 C25 123.1(3) . . ? O6 C29 C25 110.5(2) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.215 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.078 #===END data_compound_5 _database_code_CSD 157570 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Sudha Kumaraswamy' 'Praveen Kommana' 'N. Satish Kumar' 'K. C. Kumara Swamy' _publ_contact_author_name 'Dr K. C. Kumara Swamy' _publ_contact_author_address ; Dr K. C. Kumara Swamy School of Chemistry University of Hyderabad Gachibowli Hyderabad A. P. 500046 INDIA ; _publ_contact_author_email 'KCKSSC@UOHYD.ERNET.IN' _publ_section_title ; Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H53 N2 O8 P' _chemical_formula_weight 720.81 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.792(7) _cell_length_b 12.580(7) _cell_length_c 15.162(9) _cell_angle_alpha 110.66(6) _cell_angle_beta 103.36(7) _cell_angle_gamma 90.53(7) _cell_volume 2037(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12664 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 24.01 _reflns_number_total 5850 _reflns_number_gt 5108 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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 w=1/[\s^2^(Fo^2^)+(0.0844P)^2^+0.3671P] 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 5850 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.88314(4) 0.29686(4) 0.24414(3) 0.03206(16) Uani 1 d . . . O1 O 0.92169(10) 0.35550(10) 0.17821(8) 0.0372(3) Uani 1 d . . . O2 O 0.75784(10) 0.33112(10) 0.25325(8) 0.0378(3) Uani 1 d . . . O3 O 0.78925(12) 0.04988(12) 0.23259(11) 0.0548(4) Uani 1 d . . . O4 O 1.14314(13) -0.01709(15) 0.16878(11) 0.0635(4) Uani 1 d . . . O5 O 0.96294(11) -0.10242(12) 0.09012(9) 0.0485(4) Uani 1 d . . . O6 O 1.15497(15) -0.06491(14) 0.37839(12) 0.0685(5) Uani 1 d . . . O7 O 1.26731(14) 0.10314(15) 0.44741(12) 0.0724(5) Uani 1 d . . . O8 O 0.95160(11) 0.37250(10) 0.35162(8) 0.0402(3) Uani 1 d . . . N1 N 0.91300(12) 0.17158(12) 0.20615(9) 0.0354(3) Uani 1 d . . . N2 N 1.02759(14) 0.18057(12) 0.41044(10) 0.0410(4) Uani 1 d . . . C1 C 0.85289(15) 0.41247(14) 0.12196(11) 0.0331(4) Uani 1 d . . . C2 C 0.90025(17) 0.51910(15) 0.12896(12) 0.0384(4) Uani 1 d . . . C3 C 0.82726(19) 0.57142(16) 0.07298(14) 0.0479(5) Uani 1 d . . . H3 H 0.8539 0.6428 0.0760 0.058 Uiso 1 calc R . . C4 C 0.71718(19) 0.52255(19) 0.01305(15) 0.0520(5) Uani 1 d . . . C5 C 0.67908(17) 0.41415(18) 0.00488(13) 0.0456(5) Uani 1 d . . . H5 H 0.6072 0.3792 -0.0373 0.055 Uiso 1 calc R . . C6 C 0.74638(15) 0.35615(15) 0.05865(12) 0.0355(4) Uani 1 d . . . C7 C 0.70479(15) 0.23438(15) 0.04295(12) 0.0383(4) Uani 1 d . . . H7A H 0.6681 0.1949 -0.0257 0.046 Uiso 1 calc R . . H7B H 0.7728 0.1959 0.0595 0.046 Uiso 1 calc R . . C8 C 0.61953(15) 0.22281(14) 0.10050(13) 0.0367(4) Uani 1 d . . . C9 C 0.50897(16) 0.16337(16) 0.05078(14) 0.0434(4) Uani 1 d . . . H9 H 0.4897 0.1317 -0.0169 0.052 Uiso 1 calc R . . C10 C 0.42804(16) 0.15070(17) 0.09985(16) 0.0480(5) Uani 1 d . . . C11 C 0.46006(17) 0.19911(18) 0.20131(16) 0.0504(5) Uani 1 d . . . H11 H 0.4052 0.1915 0.2345 0.060 Uiso 1 calc R . . C12 C 0.56904(17) 0.25825(16) 0.25640(14) 0.0432(4) Uani 1 d . . . C13 C 0.64677(15) 0.26739(14) 0.20163(13) 0.0370(4) Uani 1 d . . . C14 C 1.02254(19) 0.57576(16) 0.19300(14) 0.0504(5) Uani 1 d . . . C15 C 1.11751(19) 0.4929(2) 0.17643(17) 0.0614(6) Uani 1 d . . . H15A H 1.1049 0.4335 0.2002 0.092 Uiso 1 calc R . . H15B H 1.1933 0.5337 0.2107 0.092 Uiso 1 calc R . . H15C H 1.1135 0.4597 0.1081 0.092 Uiso 1 calc R . . C16 C 1.0201(2) 0.6188(2) 0.30084(16) 0.0693(7) Uani 1 d . . . H16A H 0.9653 0.6751 0.3122 0.104 Uiso 1 calc R . . H16B H 1.0967 0.6524 0.3408 0.104 Uiso 1 calc R . . H16C H 0.9967 0.5560 0.3168 0.104 Uiso 1 calc R . . C17 C 1.0596(3) 0.6782(2) 0.1693(2) 0.0918(9) Uani 1 d . . . H17A H 1.0648 0.6522 0.1028 0.138 Uiso 1 calc R . . H17B H 1.1346 0.7137 0.2116 0.138 Uiso 1 calc R . . H17C H 1.0027 0.7324 0.1786 0.138 Uiso 1 calc R . . C18 C 0.6422(2) 0.5870(3) -0.0432(2) 0.0813(9) Uani 1 d . . . H18A H 0.6268 0.6578 0.0017 0.122 Uiso 1 calc R . . H18B H 0.5695 0.5415 -0.0807 0.122 Uiso 1 calc R . . H18C H 0.6830 0.6022 -0.0860 0.122 Uiso 1 calc R . . C19 C 0.30785(19) 0.0883(2) 0.0440(2) 0.0692(7) Uani 1 d . . . H19A H 0.2569 0.1404 0.0262 0.104 Uiso 1 calc R . . H19B H 0.2763 0.0578 0.0841 0.104 Uiso 1 calc R . . H19C H 0.3143 0.0271 -0.0138 0.104 Uiso 1 calc R . . C20 C 0.5999(2) 0.3084(2) 0.36894(16) 0.0581(6) Uani 1 d . . . C21 C 0.7029(2) 0.2527(3) 0.41145(17) 0.0751(7) Uani 1 d . . . H21A H 0.6865 0.1711 0.3829 0.113 Uiso 1 calc R . . H21B H 0.7140 0.2773 0.4807 0.113 Uiso 1 calc R . . H21C H 0.7728 0.2748 0.3973 0.113 Uiso 1 calc R . . C22 C 0.6295(3) 0.4394(2) 0.40684(19) 0.0805(8) Uani 1 d . . . H22A H 0.6961 0.4565 0.3860 0.121 Uiso 1 calc R . . H22B H 0.6473 0.4695 0.4767 0.121 Uiso 1 calc R . . H22C H 0.5636 0.4735 0.3814 0.121 Uiso 1 calc R . . C23 C 0.4953(3) 0.2860(3) 0.4070(2) 0.0933(10) Uani 1 d . . . H23A H 0.4294 0.3206 0.3822 0.140 Uiso 1 calc R . . H23B H 0.5161 0.3183 0.4769 0.140 Uiso 1 calc R . . H23C H 0.4753 0.2052 0.3857 0.140 Uiso 1 calc R . . C24 C 0.88590(15) 0.08151(14) 0.23095(11) 0.0342(4) Uani 1 d . . . C25 C 0.99166(16) 0.01727(15) 0.25442(12) 0.0342(4) Uani 1 d . . . H25 H 0.9680(17) -0.0401(18) 0.2699(14) 0.040(5) Uiso 1 d . . . C26 C 1.08468(16) 0.09999(16) 0.34153(12) 0.0385(4) Uani 1 d . . . H26 H 1.1291(16) 0.1447(16) 0.3169(13) 0.035(5) Uiso 1 d . . . C27 C 1.08597(19) 0.29721(16) 0.45855(13) 0.0489(5) Uani 1 d . . . H27A H 1.1684 0.2941 0.4853 0.059 Uiso 1 calc R . . H27B H 1.0524 0.3384 0.5121 0.059 Uiso 1 calc R . . C28 C 1.07433(16) 0.36146(16) 0.38999(13) 0.0445(4) Uani 1 d . . . H28A H 1.1167 0.4368 0.4243 0.053 Uiso 1 calc R . . H28B H 1.1086 0.3212 0.3366 0.053 Uiso 1 calc R . . C29 C 1.04330(15) -0.03417(15) 0.16812(12) 0.0366(4) Uani 1 d . . . C30 C 1.0035(2) -0.1569(2) 0.00301(15) 0.0633(6) Uani 1 d . . . H30A H 1.0401 -0.0998 -0.0127 0.095 Uiso 1 calc R . . H30B H 0.9381 -0.1980 -0.0501 0.095 Uiso 1 calc R . . H30C H 1.0591 -0.2089 0.0141 0.095 Uiso 1 calc R . . C31 C 1.17122(18) 0.03434(18) 0.38891(13) 0.0491(5) Uani 1 d . . . C32 C 1.3539(3) 0.0506(3) 0.5003(2) 0.0994(11) Uani 1 d . . . H32A H 1.3183 0.0216 0.5392 0.149 Uiso 1 calc R . . H32B H 1.4181 0.1066 0.5417 0.149 Uiso 1 calc R . . H32C H 1.3822 -0.0109 0.4547 0.149 Uiso 1 calc R . . C33 C 0.9895(2) 0.13448(18) 0.47564(14) 0.0539(5) Uani 1 d . . . H33A H 1.0563 0.1315 0.5245 0.081 Uiso 1 calc R . . H33B H 0.9508 0.0589 0.4391 0.081 Uiso 1 calc R . . H33C H 0.9362 0.1826 0.5063 0.081 Uiso 1 calc R . . C34 C 0.6502(5) 0.6384(5) 0.2614(3) 0.155(2) Uani 1 d . . . H34A H 0.6475 0.5842 0.1975 0.233 Uiso 1 calc R . . H34B H 0.6229 0.6003 0.2985 0.233 Uiso 1 calc R . . H34C H 0.7293 0.6716 0.2935 0.233 Uiso 1 calc R . . C35 C 0.5744(3) 0.7292(3) 0.25301(19) 0.0881(9) Uani 1 d . . . C36 C 0.6136(3) 0.8214(3) 0.23298(19) 0.0868(9) Uani 1 d . . . H36 H 0.6882 0.8243 0.2229 0.104 Uiso 1 calc R . . C37 C 0.5461(3) 0.9064(3) 0.2278(2) 0.0958(10) Uani 1 d . . . H37 H 0.5765 0.9667 0.2155 0.115 Uiso 1 calc R . . C38 C 0.4391(3) 0.9069(3) 0.2397(2) 0.0958(10) Uani 1 d . . . H38 H 0.3946 0.9662 0.2351 0.115 Uiso 1 calc R . . C39 C 0.3941(3) 0.8196(4) 0.2588(2) 0.1037(13) Uani 1 d . . . H39 H 0.3185 0.8196 0.2674 0.124 Uiso 1 calc R . . C40 C 0.4610(3) 0.7296(3) 0.2656(2) 0.0958(10) Uani 1 d . . . H40 H 0.4296 0.6703 0.2786 0.115 Uiso 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 0.0343(3) 0.0313(3) 0.0290(2) 0.01046(18) 0.00581(17) 0.00333(19) O1 0.0352(6) 0.0407(7) 0.0389(6) 0.0196(5) 0.0069(5) 0.0050(6) O2 0.0364(7) 0.0356(6) 0.0370(6) 0.0076(5) 0.0098(5) 0.0030(5) O3 0.0426(8) 0.0514(8) 0.0758(10) 0.0247(7) 0.0230(7) 0.0048(7) O4 0.0467(9) 0.0813(11) 0.0542(9) 0.0096(8) 0.0213(7) -0.0025(8) O5 0.0440(7) 0.0558(8) 0.0339(7) 0.0017(6) 0.0107(5) 0.0118(6) O6 0.0771(11) 0.0590(10) 0.0687(10) 0.0317(8) 0.0032(8) 0.0197(9) O7 0.0589(9) 0.0726(10) 0.0596(9) 0.0127(8) -0.0167(7) 0.0138(8) O8 0.0459(7) 0.0361(6) 0.0325(6) 0.0090(5) 0.0038(5) 0.0041(6) N1 0.0414(8) 0.0354(8) 0.0296(7) 0.0130(6) 0.0074(6) 0.0074(7) N2 0.0567(9) 0.0375(8) 0.0274(7) 0.0107(6) 0.0097(6) 0.0078(7) C1 0.0395(9) 0.0325(8) 0.0297(8) 0.0123(7) 0.0117(7) 0.0094(8) C2 0.0514(10) 0.0319(9) 0.0344(9) 0.0104(7) 0.0184(8) 0.0044(8) C3 0.0659(13) 0.0374(10) 0.0529(11) 0.0228(9) 0.0279(10) 0.0129(10) C4 0.0595(13) 0.0609(13) 0.0560(12) 0.0370(10) 0.0275(10) 0.0275(11) C5 0.0400(10) 0.0638(13) 0.0399(10) 0.0254(9) 0.0127(8) 0.0144(10) C6 0.0375(9) 0.0400(9) 0.0320(8) 0.0143(7) 0.0123(7) 0.0080(8) C7 0.0350(9) 0.0405(9) 0.0335(9) 0.0090(7) 0.0046(7) 0.0014(8) C8 0.0342(9) 0.0328(8) 0.0427(9) 0.0144(7) 0.0083(7) 0.0052(8) C9 0.0372(10) 0.0400(9) 0.0501(11) 0.0169(8) 0.0049(8) 0.0038(8) C10 0.0342(10) 0.0425(10) 0.0692(13) 0.0247(9) 0.0095(9) 0.0039(9) C11 0.0421(11) 0.0498(11) 0.0714(14) 0.0283(10) 0.0271(10) 0.0121(10) C12 0.0414(10) 0.0389(10) 0.0548(11) 0.0176(8) 0.0212(8) 0.0098(9) C13 0.0334(9) 0.0317(8) 0.0456(10) 0.0130(7) 0.0106(7) 0.0064(8) C14 0.0638(13) 0.0380(10) 0.0429(11) 0.0091(8) 0.0109(9) -0.0112(10) C15 0.0446(11) 0.0694(14) 0.0627(14) 0.0154(11) 0.0138(10) -0.0129(11) C16 0.0885(18) 0.0550(13) 0.0447(12) -0.0015(10) 0.0111(11) -0.0030(13) C17 0.107(2) 0.0657(16) 0.095(2) 0.0372(15) -0.0010(17) -0.0362(17) C18 0.0782(17) 0.106(2) 0.100(2) 0.0765(18) 0.0352(15) 0.0468(17) C19 0.0391(11) 0.0710(15) 0.0936(18) 0.0306(13) 0.0089(11) -0.0064(11) C20 0.0613(13) 0.0630(13) 0.0540(12) 0.0144(10) 0.0330(10) 0.0116(11) C21 0.0877(18) 0.100(2) 0.0470(12) 0.0318(13) 0.0272(12) 0.0233(16) C22 0.097(2) 0.0647(15) 0.0665(15) -0.0023(12) 0.0378(14) 0.0068(15) C23 0.0884(19) 0.123(3) 0.0715(17) 0.0192(17) 0.0516(15) 0.0020(19) C24 0.0390(10) 0.0326(9) 0.0287(8) 0.0075(7) 0.0098(7) 0.0026(8) C25 0.0425(10) 0.0314(9) 0.0307(8) 0.0133(7) 0.0099(7) 0.0045(8) C26 0.0429(10) 0.0404(9) 0.0314(9) 0.0140(7) 0.0066(7) 0.0046(9) C27 0.0627(12) 0.0424(10) 0.0305(9) 0.0088(8) -0.0023(8) 0.0037(10) C28 0.0424(10) 0.0411(10) 0.0388(10) 0.0114(8) -0.0054(8) -0.0051(8) C29 0.0394(10) 0.0365(9) 0.0356(9) 0.0157(7) 0.0085(7) 0.0094(8) C30 0.0660(14) 0.0755(15) 0.0377(11) 0.0023(10) 0.0214(10) 0.0223(12) C31 0.0540(12) 0.0539(12) 0.0349(10) 0.0135(8) 0.0065(8) 0.0142(10) C32 0.0828(19) 0.109(2) 0.0678(17) 0.0141(15) -0.0266(14) 0.0394(18) C33 0.0798(15) 0.0513(11) 0.0364(10) 0.0186(9) 0.0209(9) 0.0127(11) C34 0.181(5) 0.187(5) 0.116(3) 0.061(3) 0.059(3) 0.091(4) C35 0.088(2) 0.112(2) 0.0529(14) 0.0177(15) 0.0149(13) 0.0257(19) C36 0.0672(17) 0.129(3) 0.0566(15) 0.0249(16) 0.0165(12) -0.0070(19) C37 0.100(3) 0.105(2) 0.0657(17) 0.0221(16) 0.0039(16) -0.005(2) C38 0.078(2) 0.100(2) 0.0778(19) 0.0085(17) -0.0015(15) -0.002(2) C39 0.0532(15) 0.125(3) 0.086(2) -0.016(2) 0.0164(14) -0.0134(19) C40 0.102(2) 0.091(2) 0.0741(18) -0.0003(16) 0.0332(16) -0.027(2) _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 N1 1.5502(18) . ? P O2 1.5660(16) . ? P O1 1.5731(15) . ? P O8 1.580(2) . ? O1 C1 1.422(2) . ? O2 C13 1.426(3) . ? O3 C24 1.212(2) . ? O4 C29 1.192(2) . ? O5 C29 1.336(3) . ? O5 C30 1.450(2) . ? O6 C31 1.209(3) . ? O7 C31 1.340(3) . ? O7 C32 1.459(3) . ? O8 C28 1.457(2) . ? N1 C24 1.370(2) . ? N2 C33 1.456(3) . ? N2 C27 1.467(3) . ? N2 C26 1.471(3) . ? C1 C6 1.395(3) . ? C1 C2 1.407(3) . ? C2 C3 1.401(3) . ? C2 C14 1.541(3) . ? C3 C4 1.391(3) . ? C4 C5 1.386(3) . ? C4 C18 1.523(3) . ? C5 C6 1.400(3) . ? C6 C7 1.523(3) . ? C7 C8 1.512(3) . ? C8 C13 1.390(3) . ? C8 C9 1.399(3) . ? C9 C10 1.378(3) . ? C10 C11 1.395(3) . ? C10 C19 1.516(3) . ? C11 C12 1.397(3) . ? C12 C13 1.400(3) . ? C12 C20 1.546(3) . ? C14 C16 1.538(3) . ? C14 C17 1.540(3) . ? C14 C15 1.540(3) . ? C20 C21 1.535(3) . ? C20 C23 1.539(3) . ? C20 C22 1.549(4) . ? C24 C25 1.533(3) . ? C25 C29 1.510(3) . ? C25 C26 1.539(3) . ? C26 C31 1.528(3) . ? C27 C28 1.510(3) . ? C34 C35 1.480(5) . ? C35 C40 1.393(5) . ? C35 C36 1.398(5) . ? C36 C37 1.352(5) . ? C37 C38 1.315(5) . ? C38 C39 1.362(5) . ? C39 C40 1.406(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 N1 P O2 123.66(10) . . ? N1 P O1 106.37(9) . . ? O2 P O1 107.08(8) . . ? N1 P O8 115.93(9) . . ? O2 P O8 97.22(10) . . ? O1 P O8 105.00(9) . . ? C1 O1 P 128.49(11) . . ? C13 O2 P 129.09(11) . . ? C29 O5 C30 116.04(17) . . ? C31 O7 C32 115.4(2) . . ? C28 O8 P 121.51(13) . . ? C24 N1 P 129.88(12) . . ? C33 N2 C27 114.13(16) . . ? C33 N2 C26 113.99(15) . . ? C27 N2 C26 115.65(17) . . ? C6 C1 C2 124.02(16) . . ? C6 C1 O1 118.11(15) . . ? C2 C1 O1 117.73(16) . . ? C3 C2 C1 114.82(18) . . ? C3 C2 C14 121.73(17) . . ? C1 C2 C14 123.45(17) . . ? C4 C3 C2 123.62(19) . . ? C5 C4 C3 118.49(18) . . ? C5 C4 C18 121.4(2) . . ? C3 C4 C18 120.1(2) . . ? C4 C5 C6 121.47(19) . . ? C1 C6 C5 117.31(18) . . ? C1 C6 C7 122.85(16) . . ? C5 C6 C7 119.77(17) . . ? C8 C7 C6 115.64(15) . . ? C13 C8 C9 118.02(18) . . ? C13 C8 C7 122.76(16) . . ? C9 C8 C7 119.22(16) . . ? C10 C9 C8 121.46(19) . . ? C9 C10 C11 117.71(19) . . ? C9 C10 C19 120.3(2) . . ? C11 C10 C19 122.0(2) . . ? C10 C11 C12 124.39(19) . . ? C11 C12 C13 114.66(18) . . ? C11 C12 C20 121.89(18) . . ? C13 C12 C20 123.44(18) . . ? C8 C13 C12 123.74(18) . . ? C8 C13 O2 118.65(17) . . ? C12 C13 O2 117.53(16) . . ? C16 C14 C17 108.4(2) . . ? C16 C14 C15 109.48(19) . . ? C17 C14 C15 106.5(2) . . ? C16 C14 C2 109.46(19) . . ? C17 C14 C2 111.00(19) . . ? C15 C14 C2 111.95(17) . . ? C21 C20 C23 107.4(2) . . ? C21 C20 C12 110.74(17) . . ? C23 C20 C12 110.8(2) . . ? C21 C20 C22 110.2(2) . . ? C23 C20 C22 107.2(2) . . ? C12 C20 C22 110.4(2) . . ? O3 C24 N1 125.94(16) . . ? O3 C24 C25 120.78(16) . . ? N1 C24 C25 113.25(16) . . ? C29 C25 C24 111.91(14) . . ? C29 C25 C26 110.27(16) . . ? C24 C25 C26 108.99(15) . . ? N2 C26 C31 112.93(15) . . ? N2 C26 C25 110.08(16) . . ? C31 C26 C25 110.79(16) . . ? N2 C27 C28 112.52(15) . . ? O8 C28 C27 110.68(18) . . ? O4 C29 O5 123.73(17) . . ? O4 C29 C25 124.79(18) . . ? O5 C29 C25 111.48(16) . . ? O6 C31 O7 123.92(19) . . ? O6 C31 C26 125.4(2) . . ? O7 C31 C26 110.62(18) . . ? C40 C35 C36 115.8(3) . . ? C40 C35 C34 122.7(4) . . ? C36 C35 C34 121.5(4) . . ? C37 C36 C35 121.9(3) . . ? C38 C37 C36 122.3(4) . . ? C37 C38 C39 119.4(4) . . ? C38 C39 C40 120.5(3) . . ? C35 C40 C39 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 24.01 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.296 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.036 #===END data_compound_6 _database_code_CSD 157571 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Sudha Kumaraswamy' 'Praveen Kommana' 'N. Satish Kumar' 'K. C. Kumara Swamy' _publ_contact_author_name 'Dr K. C. Kumara Swamy' _publ_contact_author_address ; Dr K. C. Kumara Swamy School of Chemistry University of Hyderabad Gachibowli Hyderabad A. P. 500046 INDIA ; _publ_contact_author_email 'KCKSSC@UOHYD.ERNET.IN' _publ_section_title ; Novel reactions of phosphorus(III) azides and isocyanates: unusual modes of cycloaddition with dipolarophiles and an unexpected case of ring expansion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H42 F3 N2 O8 P' _chemical_formula_weight 694.67 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' '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' 'F' 'F' 0.0171 0.0103 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.455(3) _cell_length_b 10.861(3) _cell_length_c 19.023(5) _cell_angle_alpha 93.24(2) _cell_angle_beta 91.41(2) _cell_angle_gamma 107.85(2) _cell_volume 1854.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6520 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 24.97 _reflns_number_total 6520 _reflns_number_gt 4419 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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 w=1/[\s^2^(Fo^2^)+(0.1129P)^2^+0.6510P] 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 6520 _refine_ls_number_parameters 454 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1997 _refine_ls_wR_factor_gt 0.1698 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.008 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.53322(8) 0.71170(6) 0.23850(3) 0.0341(2) Uani 1 d . . . O1 O 0.4241(2) 0.61801(16) 0.17854(9) 0.0356(4) Uani 1 d . . . O2 O 0.6935(2) 0.69552(17) 0.25288(9) 0.0376(4) Uani 1 d . . . O3 O 0.4987(4) 1.0502(2) 0.26030(14) 0.0802(8) Uani 1 d . . . O5 O 0.6985(8) 1.0120(4) 0.0697(2) 0.187(3) Uani 1 d . . . O6 O 0.8166(4) 0.7803(5) 0.10611(19) 0.1228(14) Uani 1 d . . . O7 O 0.5980(4) 0.7174(4) 0.05386(15) 0.1084(12) Uani 1 d . . . O8 O 0.4679(2) 0.62466(18) 0.30576(10) 0.0415(5) Uani 1 d . . . F1 F 0.3619(6) 0.4190(4) 0.3872(2) 0.172(2) Uani 1 d . . . F2 F 0.2074(3) 0.4985(3) 0.43084(15) 0.1195(11) Uani 1 d . . . F3 F 0.4339(4) 0.5958(4) 0.44748(15) 0.1535(16) Uani 1 d . . . N1 N 0.4900(3) 0.8403(2) 0.27288(15) 0.0461(6) Uani 1 d . . . H1N H 0.454(5) 0.836(4) 0.302(2) 0.080(17) Uiso 1 d . . . C1 C 0.3407(3) 0.4871(2) 0.18113(13) 0.0338(6) Uani 1 d . . . C2 C 0.1873(3) 0.4497(3) 0.16769(14) 0.0393(6) Uani 1 d . . . C3 C 0.1127(4) 0.3195(3) 0.17374(17) 0.0544(8) Uani 1 d . . . H3 H 0.0099 0.2911 0.1664 0.065 Uiso 1 calc R . . C4 C 0.1833(4) 0.2292(3) 0.1902(2) 0.0637(9) Uani 1 d . . . C5 C 0.3363(4) 0.2709(3) 0.19771(17) 0.0525(8) Uani 1 d . . . H5 H 0.3859 0.2111 0.2064 0.063 Uiso 1 calc R . . C6 C 0.4180(3) 0.3995(2) 0.19267(14) 0.0368(6) Uani 1 d . . . C7 C 0.5856(3) 0.4379(3) 0.19175(15) 0.0409(6) Uani 1 d . . . H7A H 0.6119 0.3667 0.1684 0.049 Uiso 1 calc R . . H7B H 0.6190 0.5113 0.1628 0.049 Uiso 1 calc R . . C8 C 0.6726(3) 0.4734(3) 0.26157(15) 0.0401(6) Uani 1 d . . . C9 C 0.7085(4) 0.3773(3) 0.29627(18) 0.0530(8) Uani 1 d . . . H9 H 0.6735 0.2918 0.2777 0.064 Uiso 1 calc R . . C10 C 0.7953(4) 0.4064(3) 0.3578(2) 0.0632(9) Uani 1 d . . . C11 C 0.8473(4) 0.5334(3) 0.38392(18) 0.0581(9) Uani 1 d . . . H11 H 0.9066 0.5522 0.4253 0.070 Uiso 1 calc R . . C12 C 0.8171(3) 0.6361(3) 0.35240(15) 0.0453(7) Uani 1 d . . . C13 C 0.7256(3) 0.5992(3) 0.29112(14) 0.0386(6) Uani 1 d . . . C14 C 0.1049(3) 0.5435(3) 0.14367(16) 0.0470(7) Uani 1 d . . . C15 C 0.1763(4) 0.6094(4) 0.07924(19) 0.0689(10) Uani 1 d . . . H15A H 0.2759 0.6631 0.0919 0.103 Uiso 1 calc R . . H15B H 0.1194 0.6618 0.0621 0.103 Uiso 1 calc R . . H15C H 0.1787 0.5447 0.0431 0.103 Uiso 1 calc R . . C16 C 0.1035(5) 0.6456(4) 0.2022(2) 0.0774(12) Uani 1 d . . . H16A H 0.2032 0.7012 0.2130 0.116 Uiso 1 calc R . . H16B H 0.0636 0.6034 0.2436 0.116 Uiso 1 calc R . . H16C H 0.0429 0.6964 0.1868 0.116 Uiso 1 calc R . . C17 C -0.0570(4) 0.4709(4) 0.1229(2) 0.0731(11) Uani 1 d . . . H17A H -0.1055 0.5309 0.1072 0.110 Uiso 1 calc R . . H17B H -0.1059 0.4296 0.1628 0.110 Uiso 1 calc R . . H17C H -0.0616 0.4064 0.0855 0.110 Uiso 1 calc R . . C18 C 0.0946(6) 0.0888(4) 0.1969(4) 0.116(2) Uani 1 d . . . H18A H 0.0615 0.0475 0.1509 0.174 Uiso 1 calc R . . H18B H 0.0101 0.0843 0.2247 0.174 Uiso 1 calc R . . H18C H 0.1562 0.0454 0.2194 0.174 Uiso 1 calc R . . C19 C 0.8345(6) 0.3008(4) 0.3951(3) 0.1052(18) Uani 1 d . . . H19A H 0.9143 0.3395 0.4294 0.158 Uiso 1 calc R . . H19B H 0.8648 0.2459 0.3613 0.158 Uiso 1 calc R . . H19C H 0.7491 0.2502 0.4183 0.158 Uiso 1 calc R . . C20 C 0.8836(4) 0.7766(3) 0.38304(16) 0.0519(8) Uani 1 d . . . C21 C 0.9784(6) 0.7858(5) 0.4503(2) 0.0923(14) Uani 1 d . . . H21A H 1.0571 0.7495 0.4406 0.138 Uiso 1 calc R . . H21B H 0.9177 0.7386 0.4856 0.138 Uiso 1 calc R . . H21C H 1.0203 0.8751 0.4670 0.138 Uiso 1 calc R . . C22 C 0.9844(6) 0.8567(4) 0.3304(2) 0.0872(14) Uani 1 d . . . H22A H 1.0678 0.8253 0.3235 0.131 Uiso 1 calc R . . H22B H 1.0192 0.9459 0.3482 0.131 Uiso 1 calc R . . H22C H 0.9300 0.8497 0.2863 0.131 Uiso 1 calc R . . C23 C 0.7639(5) 0.8376(5) 0.4013(3) 0.0977(16) Uani 1 d . . . H23A H 0.8082 0.9195 0.4273 0.147 Uiso 1 calc R . . H23B H 0.6923 0.7812 0.4295 0.147 Uiso 1 calc R . . H23C H 0.7154 0.8509 0.3588 0.147 Uiso 1 calc R . . C24 C 0.5264(4) 0.9532(3) 0.23831(16) 0.0512(8) Uani 1 d . . . C25 C 0.6005(4) 0.9355(3) 0.17332(15) 0.0467(7) Uani 1 d . . . C26 C 0.6509(5) 1.0421(3) 0.1253(2) 0.0692(10) Uani 1 d . . . C27 C 0.7462(12) 1.1033(6) 0.0156(3) 0.193(4) Uani 1 d . . . H27A H 0.6785 1.1530 0.0116 0.289 Uiso 1 calc R . . H27B H 0.7475 1.0568 -0.0287 0.289 Uiso 1 calc R . . H27C H 0.8443 1.1605 0.0282 0.289 Uiso 1 calc R . . C28 C 0.6162(3) 0.8182(2) 0.16539(13) 0.0382(6) Uani 1 d . . . C29 C 0.6894(4) 0.7724(3) 0.10568(17) 0.0535(8) Uani 1 d . . . C30 C 0.6608(9) 0.6739(4) -0.0082(2) 0.184(4) Uani 1 d . . . H30A H 0.7319 0.7468 -0.0268 0.276 Uiso 1 calc R . . H30B H 0.5828 0.6342 -0.0432 0.276 Uiso 1 calc R . . H30C H 0.7092 0.6120 0.0045 0.276 Uiso 1 calc R . . C31 C 0.3300(4) 0.5955(3) 0.33588(15) 0.0559(8) Uani 1 d R . . H31A H 0.2535 0.5424 0.3024 0.067 Uiso 1 calc R . . H31B H 0.3068 0.6748 0.3482 0.067 Uiso 1 calc R . . C32 C 0.3335(5) 0.5254(4) 0.3994(2) 0.0711(10) Uani 1 d . . . N2 N 0.3927(5) 0.9119(4) 0.4192(2) 0.1035(13) Uani 1 d . . . C33 C 0.3962(6) 1.0174(5) 0.4177(2) 0.0875(13) Uani 1 d . . . C34 C 0.4010(8) 1.1499(5) 0.4146(3) 0.130(2) Uani 1 d . . . H34A H 0.4673 1.1892 0.3791 0.195 Uiso 1 calc R . . H34B H 0.4357 1.1955 0.4595 0.195 Uiso 1 calc R . . H34C H 0.3031 1.1538 0.4032 0.195 Uiso 1 calc R . . O4A O 0.6957(9) 1.1545(4) 0.1456(3) 0.117(2) Uani 0.65 d P . . O4B O 0.5586(15) 1.1012(12) 0.1096(6) 0.117(4) Uani 0.35 d P . . 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 0.0452(4) 0.0287(3) 0.0327(4) 0.0030(3) -0.0010(3) 0.0179(3) O1 0.0444(10) 0.0284(9) 0.0366(9) 0.0031(7) -0.0047(8) 0.0155(8) O2 0.0411(10) 0.0350(9) 0.0403(10) 0.0054(8) -0.0040(8) 0.0168(8) O3 0.137(3) 0.0428(13) 0.0783(17) 0.0027(12) 0.0150(16) 0.0527(15) O5 0.386(8) 0.081(2) 0.113(3) 0.064(2) 0.107(4) 0.085(4) O6 0.101(3) 0.208(4) 0.089(2) 0.028(2) 0.033(2) 0.087(3) O7 0.107(2) 0.134(3) 0.0550(17) -0.0374(18) 0.0165(16) 0.001(2) O8 0.0529(12) 0.0409(10) 0.0387(10) 0.0103(8) 0.0065(9) 0.0244(9) F1 0.269(5) 0.115(3) 0.188(4) 0.100(3) 0.110(4) 0.117(3) F2 0.109(2) 0.161(3) 0.0883(18) 0.0552(18) 0.0439(16) 0.0299(19) F3 0.134(3) 0.236(4) 0.0640(17) 0.038(2) -0.0268(18) 0.015(3) N1 0.0677(18) 0.0381(13) 0.0407(14) 0.0036(11) 0.0032(13) 0.0281(12) C1 0.0406(14) 0.0312(13) 0.0309(13) 0.0045(10) -0.0004(10) 0.0129(11) C2 0.0417(15) 0.0446(15) 0.0338(13) 0.0072(11) -0.0013(11) 0.0158(12) C3 0.0420(17) 0.0582(19) 0.0591(19) 0.0164(15) -0.0050(14) 0.0082(14) C4 0.060(2) 0.0412(17) 0.082(2) 0.0202(16) -0.0095(18) 0.0026(15) C5 0.060(2) 0.0354(15) 0.063(2) 0.0103(14) -0.0121(15) 0.0167(14) C6 0.0438(15) 0.0324(13) 0.0364(14) 0.0008(10) -0.0053(11) 0.0155(11) C7 0.0470(16) 0.0344(14) 0.0470(15) -0.0024(11) -0.0032(12) 0.0226(12) C8 0.0398(15) 0.0376(14) 0.0483(15) 0.0068(12) -0.0031(12) 0.0195(12) C9 0.0567(19) 0.0367(15) 0.070(2) 0.0123(14) -0.0082(16) 0.0210(14) C10 0.060(2) 0.057(2) 0.078(2) 0.0269(18) -0.0132(18) 0.0234(16) C11 0.0562(19) 0.064(2) 0.0542(19) 0.0196(16) -0.0157(15) 0.0180(16) C12 0.0433(16) 0.0525(17) 0.0415(15) 0.0095(13) -0.0030(12) 0.0163(13) C13 0.0396(14) 0.0400(14) 0.0409(14) 0.0103(11) -0.0012(11) 0.0179(12) C14 0.0457(16) 0.0565(18) 0.0448(16) 0.0080(13) -0.0023(13) 0.0241(14) C15 0.067(2) 0.089(3) 0.064(2) 0.0343(19) 0.0013(18) 0.040(2) C16 0.082(3) 0.096(3) 0.074(2) -0.015(2) -0.014(2) 0.062(2) C17 0.050(2) 0.091(3) 0.082(3) 0.015(2) -0.0125(18) 0.0284(19) C18 0.089(3) 0.053(2) 0.189(6) 0.050(3) -0.030(4) -0.007(2) C19 0.119(4) 0.076(3) 0.130(4) 0.038(3) -0.047(3) 0.044(3) C20 0.0539(18) 0.0542(18) 0.0436(16) 0.0002(13) -0.0103(14) 0.0125(14) C21 0.103(3) 0.091(3) 0.068(3) -0.001(2) -0.039(2) 0.011(3) C22 0.111(4) 0.058(2) 0.067(2) -0.0006(19) -0.002(2) -0.010(2) C23 0.089(3) 0.101(3) 0.103(3) -0.051(3) -0.030(3) 0.043(3) C24 0.073(2) 0.0304(14) 0.0544(18) 0.0008(13) -0.0044(15) 0.0228(14) C25 0.0643(19) 0.0313(14) 0.0456(16) 0.0039(12) -0.0078(14) 0.0170(13) C26 0.112(3) 0.0402(19) 0.061(2) 0.0126(16) 0.008(2) 0.0306(19) C27 0.353(13) 0.098(4) 0.102(5) 0.065(4) 0.050(6) 0.021(6) C28 0.0490(16) 0.0326(13) 0.0338(13) 0.0050(10) -0.0042(11) 0.0138(11) C29 0.071(2) 0.0475(17) 0.0483(18) 0.0152(14) 0.0138(16) 0.0241(16) C30 0.240(9) 0.200(8) 0.083(4) -0.056(5) 0.064(5) 0.033(7) C31 0.060(2) 0.064(2) 0.0493(18) 0.0112(15) 0.0078(15) 0.0258(16) C32 0.082(3) 0.078(3) 0.055(2) 0.0244(19) 0.017(2) 0.023(2) N2 0.139(4) 0.089(3) 0.084(3) -0.013(2) 0.014(2) 0.041(3) C33 0.102(3) 0.085(3) 0.071(3) -0.018(2) 0.020(2) 0.026(3) C34 0.199(7) 0.076(3) 0.122(4) -0.005(3) 0.057(4) 0.050(4) O4A 0.187(6) 0.036(2) 0.127(5) 0.022(3) 0.058(4) 0.027(3) O4B 0.171(11) 0.112(8) 0.116(8) 0.086(7) 0.040(7) 0.097(8) _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 O2 1.5971(19) . ? P O1 1.6025(19) . ? P O8 1.6520(19) . ? P N1 1.675(3) . ? P C28 1.889(3) . ? O1 C1 1.403(3) . ? O2 C13 1.409(3) . ? O3 C24 1.215(3) . ? O5 C26 1.226(5) . ? O5 C27 1.452(5) . ? O6 C29 1.178(5) . ? O7 C29 1.285(4) . ? O7 C30 1.453(4) . ? O8 C31 1.390(4) . ? F1 C32 1.275(5) . ? F2 C32 1.306(5) . ? F3 C32 1.324(5) . ? N1 C24 1.378(4) . ? C1 C6 1.389(4) . ? C1 C2 1.394(4) . ? C2 C3 1.386(4) . ? C2 C14 1.541(4) . ? C3 C4 1.389(5) . ? C4 C5 1.378(5) . ? C4 C18 1.513(5) . ? C5 C6 1.383(4) . ? C6 C7 1.511(4) . ? C7 C8 1.511(4) . ? C8 C13 1.383(4) . ? C8 C9 1.388(4) . ? C9 C10 1.377(5) . ? C10 C11 1.373(5) . ? C10 C19 1.515(4) . ? C11 C12 1.396(4) . ? C12 C13 1.397(4) . ? C12 C20 1.535(4) . ? C14 C15 1.521(5) . ? C14 C17 1.522(5) . ? C14 C16 1.530(5) . ? C20 C23 1.515(5) . ? C20 C22 1.518(5) . ? C20 C21 1.524(5) . ? C24 C25 1.468(5) . ? C25 C28 1.328(4) . ? C25 C26 1.486(4) . ? C26 O4A 1.200(6) . ? C26 O4B 1.270(10) . ? C28 C29 1.484(4) . ? C31 C32 1.469(5) . ? N2 C33 1.137(6) . ? C33 C34 1.430(7) . ? O4A O4B 1.391(13) . ? 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 O2 P O1 118.61(10) . . ? O2 P O8 90.65(10) . . ? O1 P O8 97.04(10) . . ? O2 P N1 121.39(13) . . ? O1 P N1 118.93(12) . . ? O8 P N1 92.66(12) . . ? O2 P C28 87.63(11) . . ? O1 P C28 86.37(11) . . ? O8 P C28 176.59(11) . . ? N1 P C28 85.74(13) . . ? C1 O1 P 128.48(16) . . ? C13 O2 P 126.54(17) . . ? C26 O5 C27 121.8(5) . . ? C29 O7 C30 116.7(5) . . ? C31 O8 P 130.88(18) . . ? C24 N1 P 119.7(2) . . ? C6 C1 C2 123.1(2) . . ? C6 C1 O1 117.5(2) . . ? C2 C1 O1 119.3(2) . . ? C3 C2 C1 115.5(3) . . ? C3 C2 C14 121.3(3) . . ? C1 C2 C14 123.1(2) . . ? C2 C3 C4 123.5(3) . . ? C5 C4 C3 117.9(3) . . ? C5 C4 C18 121.3(3) . . ? C3 C4 C18 120.8(3) . . ? C4 C5 C6 121.7(3) . . ? C5 C6 C1 117.8(3) . . ? C5 C6 C7 119.8(2) . . ? C1 C6 C7 122.0(2) . . ? C8 C7 C6 117.8(2) . . ? C13 C8 C9 117.9(3) . . ? C13 C8 C7 123.1(2) . . ? C9 C8 C7 119.0(3) . . ? C10 C9 C8 121.0(3) . . ? C11 C10 C9 118.5(3) . . ? C11 C10 C19 120.8(3) . . ? C9 C10 C19 120.6(3) . . ? C10 C11 C12 124.3(3) . . ? C11 C12 C13 114.2(3) . . ? C11 C12 C20 121.5(3) . . ? C13 C12 C20 124.3(3) . . ? C8 C13 C12 124.1(2) . . ? C8 C13 O2 116.5(2) . . ? C12 C13 O2 119.2(2) . . ? C15 C14 C17 107.4(3) . . ? C15 C14 C16 110.0(3) . . ? C17 C14 C16 106.5(3) . . ? C15 C14 C2 109.9(2) . . ? C17 C14 C2 110.9(3) . . ? C16 C14 C2 112.1(3) . . ? C23 C20 C22 109.2(4) . . ? C23 C20 C21 107.0(3) . . ? C22 C20 C21 106.9(3) . . ? C23 C20 C12 111.8(3) . . ? C22 C20 C12 109.8(3) . . ? C21 C20 C12 112.0(3) . . ? O3 C24 N1 123.2(3) . . ? O3 C24 C25 127.3(3) . . ? N1 C24 C25 109.5(2) . . ? C28 C25 C24 112.1(3) . . ? C28 C25 C26 126.9(3) . . ? C24 C25 C26 121.0(3) . . ? O4A C26 O5 116.5(5) . . ? O4A C26 O4B 68.5(6) . . ? O5 C26 O4B 106.8(6) . . ? O4A C26 C25 123.1(4) . . ? O5 C26 C25 114.9(3) . . ? O4B C26 C25 116.8(6) . . ? C25 C28 C29 124.7(3) . . ? C25 C28 P 112.9(2) . . ? C29 C28 P 122.41(19) . . ? O6 C29 O7 122.8(4) . . ? O6 C29 C28 124.3(3) . . ? O7 C29 C28 112.8(3) . . ? O8 C31 C32 109.3(3) . . ? F1 C32 F2 107.3(4) . . ? F1 C32 F3 107.2(4) . . ? F2 C32 F3 104.8(4) . . ? F1 C32 C31 113.4(3) . . ? F2 C32 C31 111.7(4) . . ? F3 C32 C31 111.9(3) . . ? N2 C33 C34 179.0(5) . . ? C26 O4A O4B 58.1(5) . . ? C26 O4B O4A 53.4(5) . . ? 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 N1 H1N N2 0.66(4) 2.47(4) 3.085(5) 156(5) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.443 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.057 #==#END#===