# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author # Name and address of author for correspondence ; Esra Tanriverdi Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; _publ_contact_author_phone '+90 262 605 31 28' _publ_contact_author_fax '+90 262 605 31 01' _publ_contact_author_email etanriverdi@gyte.edu.tr _publ_contact_letter ; Please consider this CIF file submission for publication of one Regular Structures in Polyhedron. ; _publ_section_title ; Stereo-selectivity in cyclotriphosphazene derivative bearing an exocyclic P-O moiety ; loop_ _publ_author_name _publ_author_address E.Tanriverdi ; Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; S.Besli ; Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; G.Ciftci ; Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; D.Davies ; University of London Birkbeck College School of Biol. and Chem. Sciences Malet Street, WC1E 7HX London, UK. ; A.Kilic ; Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; F.Yuksel ; Gebze Institute of Technology Department of Chemistry P.O. Box:141, 41400 Gebze, Kocaeli Turkey ; _publ_section_abstract ; Nucleophilic substitution reactions of N3P3Cl4[O(CH2)2NCH3], (1) with the sodium salts of mono- and di-functional alcohols [methanol (2), phenol (3), tetraethyleneglycol (4) and 1,3-propanediol (5)] were carried out in order to investigate a possible directing effect of the spiro O-moiety on the formation of mono-substituted (2a,3a), non-geminal bis-substituted (2c,3c) and ansa (4a,5a) derivatives. Compounds isolated from the reactions were characterized by elemental analysis, mass spectrometry, 1H and 31P NMR spectroscopy and X-ray crystallographic analysis showed that the substituent OR in compounds (2a, 3a and 2c, 3c) and the ansa-ring in compounds (4a, 5a) formed cis to the P-O moiety of the exocyclic [O(CH2)2NCH3] spiro ring. The formation of products (2a-d, 3a-d, 4a, 5a and 5b) was quantified from the 31P NMR spectra of the reaction mixtures, which showed an overwhelming preference for derivatives (2a, 3a, 2c, 3c, 4a, 5a) with the substituent cis to the P-O moiety of the exocyclic spiro ring, except for reaction with 1,3-propanediol where the six-membered ring spiro derivative (5b) was about three times more abundant than the eight-membered ring ansa-derivative (5a). Formation of products with the substituent cis to the P-O moiety may be explained with cation-assisted mechanism. ; _publ_contact_author_name 'Esra Tanriverdi' data_ETE1 _database_code_depnum_ccdc_archive 'CCDC 865160' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 Cl4 N4 O P3' _chemical_formula_iupac ? _chemical_formula_weight 349.84 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.2125(16) _cell_length_b 8.7839(7) _cell_length_c 16.9830(13) _cell_angle_alpha 90 _cell_angle_beta 116.224(6) _cell_angle_gamma 90 _cell_volume 2571.1(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9923 _cell_measurement_theta_min 2.3634 _cell_measurement_theta_max 28.3378 _cell_measurement_temperature 121.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.180 _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.80 _exptl_special_details ; ; _diffrn_ambient_temperature 121.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 19661 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _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. ; _reflns_number_total 4547 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.0626 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_number_reflns 4547 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.7557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.339 _refine_diff_density_min -0.340 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 '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' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.04013(4) 0.72553(8) 0.43726(5) 0.01746(17) Uani d . 1 . . P P2 0.13766(4) 0.89049(8) 0.38570(4) 0.01854(15) Uani d . 1 . . P P3 0.13778(4) 0.58069(8) 0.37879(4) 0.01667(14) Uani d . 1 . . P P4 0.46138(4) 0.77496(8) 0.39738(5) 0.01674(17) Uani d . 1 . . P P5 0.36042(3) 0.92127(8) 0.24322(4) 0.01717(14) Uani d . 1 . . P P6 0.36493(4) 0.61151(8) 0.24769(4) 0.01765(15) Uani d . 1 . . N N1 0.07385(13) 0.8808(2) 0.41865(15) 0.0231(5) Uani d . 1 . . N N2 0.16950(14) 0.7383(2) 0.36289(18) 0.0221(5) Uani d . 1 . . N N3 0.07358(12) 0.5778(2) 0.41145(14) 0.0202(4) Uani d . 1 . . N N4 0.42473(12) 0.9238(2) 0.34045(14) 0.0210(4) Uani d . 1 . . N N5 0.33042(13) 0.7637(2) 0.19474(17) 0.0208(5) Uani d . 1 . . N N6 0.43019(12) 0.6202(2) 0.34392(14) 0.0225(5) Uani d . 1 . . N N7 0.04807(13) 0.7140(2) 0.53709(14) 0.0208(5) Uani d . 1 . . N N8 0.45491(13) 0.7802(2) 0.49065(14) 0.0206(5) Uani d . 1 . . O O1 -0.05085(11) 0.7300(2) 0.38822(13) 0.0247(5) Uani d . 1 . . O O2 0.55318(11) 0.7777(2) 0.43744(13) 0.0240(4) Uani d . 1 . . Cl Cl1 0.22816(4) 1.00740(9) 0.47335(5) 0.03647(18) Uani d . 1 . . Cl Cl2 0.10240(4) 1.02796(9) 0.28204(5) 0.03011(16) Uani d . 1 . . Cl Cl3 0.22826(4) 0.45752(8) 0.46207(5) 0.03174(17) Uani d . 1 . . Cl Cl4 0.10291(4) 0.45608(9) 0.27013(4) 0.02720(15) Uani d . 1 . . Cl Cl5 0.39413(4) 1.05138(8) 0.17049(4) 0.02796(16) Uani d . 1 . . Cl Cl6 0.26852(4) 1.03907(9) 0.23702(5) 0.03400(18) Uani d . 1 . . Cl Cl7 0.27696(4) 0.48681(9) 0.24692(5) 0.03429(17) Uani d . 1 . . Cl Cl8 0.40003(4) 0.48026(8) 0.17665(5) 0.02900(16) Uani d . 1 . . C C1 -0.08564(15) 0.7138(3) 0.44925(18) 0.0280(6) Uani d . 1 . . H H1A -0.101 0.6068 0.4512 0.034 Uiso calc R 1 . . H H1B -0.1321 0.7793 0.4309 0.034 Uiso calc R 1 . . C C2 -0.02395(18) 0.7624(3) 0.5377(2) 0.0260(7) Uani d . 1 . . H H2A -0.0247 0.8742 0.545 0.031 Uiso calc R 1 . . H H2B -0.0313 0.7121 0.5856 0.031 Uiso calc R 1 . . C C3 0.12036(19) 0.7618(3) 0.6103(2) 0.0346(8) Uani d . 1 . . H H3A 0.1239 0.8731 0.611 0.052 Uiso calc R 1 . . H H3B 0.1643 0.7181 0.6035 0.052 Uiso calc R 1 . . H H3C 0.1214 0.7263 0.6655 0.052 Uiso calc R 1 . . C C4 0.58856(15) 0.7958(3) 0.53317(17) 0.0272(6) Uani d . 1 . . H H4A 0.6002 0.9043 0.5494 0.033 Uiso calc R 1 . . H H4B 0.6374 0.7369 0.561 0.033 Uiso calc R 1 . . C C5 0.52994(18) 0.7363(3) 0.5622(2) 0.0264(7) Uani d . 1 . . H H5A 0.5339 0.6244 0.5696 0.032 Uiso calc R 1 . . H H5B 0.5374 0.7837 0.6183 0.032 Uiso calc R 1 . . C C6 0.38464(19) 0.7235(4) 0.4934(2) 0.0354(7) Uani d . 1 . . H H6A 0.3869 0.6122 0.4978 0.053 Uiso calc R 1 . . H H6B 0.3392 0.7539 0.4397 0.053 Uiso calc R 1 . . H H6C 0.3806 0.7663 0.5445 0.053 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0219(4) 0.0168(4) 0.0160(3) 0.0022(2) 0.0104(3) 0.0014(2) P2 0.0212(3) 0.0151(3) 0.0201(3) 0.0004(2) 0.0099(3) 0.0017(2) P3 0.0189(3) 0.0149(3) 0.0176(3) 0.0002(2) 0.0093(3) -0.0014(2) P4 0.0221(4) 0.0156(4) 0.0140(3) 0.0020(2) 0.0093(3) 0.0010(2) P5 0.0193(3) 0.0142(3) 0.0181(3) 0.0010(2) 0.0084(3) 0.0025(2) P6 0.0203(3) 0.0139(3) 0.0196(3) 0.0010(2) 0.0096(3) -0.0009(2) N1 0.0328(11) 0.0159(11) 0.0275(11) 0.0065(9) 0.0197(10) 0.0036(9) N2 0.0248(12) 0.0191(12) 0.0280(14) -0.0001(8) 0.0167(12) -0.0002(8) N3 0.0265(10) 0.0160(10) 0.0230(10) -0.0011(8) 0.0153(9) -0.0014(9) N4 0.0297(11) 0.0144(10) 0.0167(10) 0.0004(8) 0.0084(9) 0.0004(8) N5 0.0218(12) 0.0161(11) 0.0198(13) 0.0002(7) 0.0048(11) 0.0002(8) N6 0.0318(11) 0.0158(11) 0.0188(10) 0.0029(9) 0.0103(9) 0.0014(9) N7 0.0279(11) 0.0212(11) 0.0171(11) 0.0009(9) 0.0134(9) -0.0012(9) N8 0.0280(12) 0.0207(11) 0.0151(11) -0.0005(9) 0.0113(9) 0.0005(9) O1 0.0224(10) 0.0329(11) 0.0198(10) 0.0060(7) 0.0102(8) 0.0060(7) O2 0.0229(10) 0.0289(10) 0.0195(10) -0.0005(7) 0.0088(8) -0.0021(7) Cl1 0.0316(3) 0.0277(4) 0.0405(4) -0.0073(3) 0.0072(3) -0.0106(3) Cl2 0.0303(3) 0.0315(4) 0.0342(4) 0.0082(3) 0.0193(3) 0.0169(3) Cl3 0.0248(3) 0.0292(4) 0.0363(4) 0.0079(3) 0.0091(3) 0.0097(3) Cl4 0.0303(3) 0.0310(4) 0.0260(3) -0.0084(3) 0.0176(3) -0.0130(3) Cl5 0.0303(3) 0.0302(4) 0.0199(3) -0.0089(3) 0.0080(3) 0.0071(3) Cl6 0.0269(3) 0.0267(4) 0.0492(4) 0.0077(3) 0.0176(3) -0.0023(3) Cl7 0.0302(3) 0.0274(4) 0.0475(4) -0.0058(3) 0.0192(3) 0.0055(3) Cl8 0.0295(3) 0.0315(4) 0.0228(3) 0.0096(3) 0.0086(3) -0.0079(3) C1 0.0268(13) 0.0294(15) 0.0354(15) 0.0047(12) 0.0206(12) 0.0084(12) C2 0.0396(17) 0.0185(14) 0.0318(17) 0.0025(10) 0.0265(15) 0.0002(10) C3 0.0385(17) 0.0443(19) 0.0177(15) -0.0038(12) 0.0095(14) -0.0022(11) C4 0.0262(13) 0.0289(14) 0.0202(13) 0.0020(12) 0.0045(11) -0.0035(12) C5 0.0385(16) 0.0182(14) 0.0163(15) 0.0048(10) 0.0064(14) 0.0019(9) C6 0.0413(17) 0.0453(18) 0.0300(17) -0.0052(13) 0.0252(15) -0.0027(13) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.570(2) ? P1 N3 . 1.593(2) ? P1 N1 . 1.600(2) ? P1 N7 . 1.637(2) ? P2 N1 . 1.559(2) ? P2 N2 . 1.587(2) ? P2 Cl2 . 1.9906(9) ? P2 Cl1 . 2.0016(9) ? P3 N3 . 1.560(2) ? P3 N2 . 1.583(2) ? P3 Cl4 . 1.9900(9) ? P3 Cl3 . 2.0049(9) ? P4 O2 . 1.586(2) ? P4 N4 . 1.594(2) ? P4 N6 . 1.597(2) ? P4 N8 . 1.643(2) ? P5 N4 . 1.565(2) ? P5 N5 . 1.583(2) ? P5 Cl5 . 1.9895(9) ? P5 Cl6 . 2.0087(9) ? P6 N6 . 1.561(2) ? P6 N5 . 1.583(2) ? P6 Cl8 . 1.9896(9) ? P6 Cl7 . 2.0091(9) ? N7 C2 . 1.452(4) ? N7 C3 . 1.458(4) ? N8 C6 . 1.459(4) ? N8 C5 . 1.468(4) ? O1 C1 . 1.468(3) ? O2 C4 . 1.468(3) ? C1 C2 . 1.507(4) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 C5 . 1.508(4) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? C5 H5A . 0.99 ? C5 H5B . 0.99 ? C6 H6A . 0.98 ? C6 H6B . 0.98 ? C6 H6C . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N3 . . 111.37(11) ? O1 P1 N1 . . 109.08(11) ? N3 P1 N1 . . 113.10(12) ? O1 P1 N7 . . 97.09(12) ? N3 P1 N7 . . 111.72(12) ? N1 P1 N7 . . 113.38(12) ? N1 P2 N2 . . 119.40(12) ? N1 P2 Cl2 . . 109.65(9) ? N2 P2 Cl2 . . 108.19(10) ? N1 P2 Cl1 . . 108.88(9) ? N2 P2 Cl1 . . 108.16(9) ? Cl2 P2 Cl1 . . 101.00(4) ? N3 P3 N2 . . 119.95(12) ? N3 P3 Cl4 . . 109.00(9) ? N2 P3 Cl4 . . 108.67(10) ? N3 P3 Cl3 . . 108.39(9) ? N2 P3 Cl3 . . 108.25(9) ? Cl4 P3 Cl3 . . 100.90(4) ? O2 P4 N4 . . 110.95(11) ? O2 P4 N6 . . 108.88(11) ? N4 P4 N6 . . 113.55(13) ? O2 P4 N8 . . 97.44(12) ? N4 P4 N8 . . 111.12(12) ? N6 P4 N8 . . 113.75(12) ? N4 P5 N5 . . 119.83(12) ? N4 P5 Cl5 . . 108.96(9) ? N5 P5 Cl5 . . 108.85(10) ? N4 P5 Cl6 . . 108.27(9) ? N5 P5 Cl6 . . 108.28(9) ? Cl5 P5 Cl6 . . 101.03(4) ? N6 P6 N5 . . 119.62(12) ? N6 P6 Cl8 . . 109.41(9) ? N5 P6 Cl8 . . 108.29(10) ? N6 P6 Cl7 . . 108.51(9) ? N5 P6 Cl7 . . 108.46(9) ? Cl8 P6 Cl7 . . 100.94(4) ? P2 N1 P1 . . 124.65(13) ? P3 N2 P2 . . 118.41(16) ? P3 N3 P1 . . 124.25(13) ? P5 N4 P4 . . 124.01(13) ? P6 N5 P5 . . 118.54(16) ? P6 N6 P4 . . 124.24(13) ? C2 N7 C3 . . 117.5(2) ? C2 N7 P1 . . 109.65(18) ? C3 N7 P1 . . 118.87(19) ? C6 N8 C5 . . 117.9(2) ? C6 N8 P4 . . 119.10(19) ? C5 N8 P4 . . 109.03(18) ? C1 O1 P1 . . 111.77(17) ? C4 O2 P4 . . 111.08(16) ? O1 C1 C2 . . 105.9(2) ? O1 C1 H1A . . 110.6 ? C2 C1 H1A . . 110.6 ? O1 C1 H1B . . 110.6 ? C2 C1 H1B . . 110.6 ? H1A C1 H1B . . 108.7 ? N7 C2 C1 . . 104.0(2) ? N7 C2 H2A . . 111.0 ? C1 C2 H2A . . 111.0 ? N7 C2 H2B . . 111.0 ? C1 C2 H2B . . 111.0 ? H2A C2 H2B . . 109.0 ? N7 C3 H3A . . 109.5 ? N7 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N7 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O2 C4 C5 . . 106.1(2) ? O2 C4 H4A . . 110.5 ? C5 C4 H4A . . 110.5 ? O2 C4 H4B . . 110.5 ? C5 C4 H4B . . 110.5 ? H4A C4 H4B . . 108.7 ? N8 C5 C4 . . 103.9(2) ? N8 C5 H5A . . 111.0 ? C4 C5 H5A . . 111.0 ? N8 C5 H5B . . 111.0 ? C4 C5 H5B . . 111.0 ? H5A C5 H5B . . 109.0 ? N8 C6 H6A . . 109.5 ? N8 C6 H6B . . 109.5 ? H6A C6 H6B . . 109.5 ? N8 C6 H6C . . 109.5 ? H6A C6 H6C . . 109.5 ? H6B C6 H6C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 P2 N1 P1 . . . . 3.8(2) ? Cl2 P2 N1 P1 . . . . 129.36(14) ? Cl1 P2 N1 P1 . . . . -121.00(15) ? O1 P1 N1 P2 . . . . -129.11(17) ? N3 P1 N1 P2 . . . . -4.6(2) ? N7 P1 N1 P2 . . . . 123.93(17) ? N3 P3 N2 P2 . . . . 3.2(2) ? Cl4 P3 N2 P2 . . . . 129.41(15) ? Cl3 P3 N2 P2 . . . . -121.84(15) ? N1 P2 N2 P3 . . . . -2.8(2) ? Cl2 P2 N2 P3 . . . . -129.07(15) ? Cl1 P2 N2 P3 . . . . 122.33(14) ? N2 P3 N3 P1 . . . . -4.5(2) ? Cl4 P3 N3 P1 . . . . -130.59(14) ? Cl3 P3 N3 P1 . . . . 120.43(14) ? O1 P1 N3 P3 . . . . 128.18(16) ? N1 P1 N3 P3 . . . . 4.9(2) ? N7 P1 N3 P3 . . . . -124.46(16) ? N5 P5 N4 P4 . . . . -2.3(2) ? Cl5 P5 N4 P4 . . . . -128.55(14) ? Cl6 P5 N4 P4 . . . . 122.40(14) ? O2 P4 N4 P5 . . . . 126.70(16) ? N6 P4 N4 P5 . . . . 3.7(2) ? N8 P4 N4 P5 . . . . -126.05(16) ? N6 P6 N5 P5 . . . . -3.2(2) ? Cl8 P6 N5 P5 . . . . -129.35(14) ? Cl7 P6 N5 P5 . . . . 121.92(14) ? N4 P5 N5 P6 . . . . 1.9(2) ? Cl5 P5 N5 P6 . . . . 128.16(14) ? Cl6 P5 N5 P6 . . . . -122.85(14) ? N5 P6 N6 P4 . . . . 5.0(2) ? Cl8 P6 N6 P4 . . . . 130.69(14) ? Cl7 P6 N6 P4 . . . . -120.03(15) ? O2 P4 N6 P6 . . . . -129.20(16) ? N4 P4 N6 P6 . . . . -5.1(2) ? N8 P4 N6 P6 . . . . 123.34(17) ? O1 P1 N7 C2 . . . . -18.52(19) ? N3 P1 N7 C2 . . . . -134.93(17) ? N1 P1 N7 C2 . . . . 95.85(19) ? O1 P1 N7 C3 . . . . -157.6(2) ? N3 P1 N7 C3 . . . . 86.0(2) ? N1 P1 N7 C3 . . . . -43.3(2) ? O2 P4 N8 C6 . . . . -157.1(2) ? N4 P4 N8 C6 . . . . 87.0(2) ? N6 P4 N8 C6 . . . . -42.6(2) ? O2 P4 N8 C5 . . . . -17.79(18) ? N4 P4 N8 C5 . . . . -133.71(17) ? N6 P4 N8 C5 . . . . 96.66(18) ? N3 P1 O1 C1 . . . . 113.52(18) ? N1 P1 O1 C1 . . . . -120.95(18) ? N7 P1 O1 C1 . . . . -3.16(19) ? N4 P4 O2 C4 . . . . 111.47(18) ? N6 P4 O2 C4 . . . . -122.87(18) ? N8 P4 O2 C4 . . . . -4.58(19) ? P1 O1 C1 C2 . . . . 22.7(2) ? C3 N7 C2 C1 . . . . 172.5(2) ? P1 N7 C2 C1 . . . . 32.7(2) ? O1 C1 C2 N7 . . . . -33.8(3) ? P4 O2 C4 C5 . . . . 24.7(2) ? C6 N8 C5 C4 . . . . 172.9(2) ? P4 N8 C5 C4 . . . . 33.1(2) ? O2 C4 C5 N8 . . . . -35.4(3) ? #===END data_ETE2a _database_code_depnum_ccdc_archive 'CCDC 865161' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Cl3 N4 O2 P3' _chemical_formula_iupac ? _chemical_formula_weight 345.42 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.790(3) _cell_length_b 6.5492(6) _cell_length_c 15.5333(14) _cell_angle_alpha 90 _cell_angle_beta 114.5980(10) _cell_angle_gamma 90 _cell_volume 2755.5(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3845 _cell_measurement_theta_min 2.8844 _cell_measurement_theta_max 28.0116 _cell_measurement_temperature 296.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_min 0.140 _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.87 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 7000 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _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. ; _reflns_number_total 2353 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_gt 0.1101 _refine_ls_wR_factor_ref 0.1143 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_number_reflns 2353 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+4.5586P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.483 _refine_diff_density_min -0.456 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.81055(3) 0.76355(13) 0.90247(6) 0.0492(2) Uani d . 1 . . P P2 0.90378(3) 0.62500(14) 1.02294(6) 0.0538(2) Uani d . 1 . . P P3 0.89100(3) 0.80529(16) 0.85693(6) 0.0575(3) Uani d . 1 . . N N1 0.84716(9) 0.6440(4) 0.9936(2) 0.0598(7) Uani d . 1 . . N N2 0.92543(9) 0.6933(5) 0.9500(2) 0.0688(9) Uani d . 1 . . N N3 0.83543(10) 0.8355(5) 0.8341(2) 0.0661(8) Uani d . 1 . . N N4 0.78147(10) 0.9459(4) 0.9287(2) 0.0635(8) Uani d . 1 . . O O1 0.76403(9) 0.6279(4) 0.8454(2) 0.0725(7) Uani d . 1 . . O O2 0.91938(9) 0.4015(4) 1.0575(2) 0.0715(7) Uani d . 1 . . Cl Cl1 0.94005(5) 0.7878(2) 1.14214(9) 0.1019(4) Uani d . 1 . . Cl Cl2 0.89713(4) 0.6699(2) 0.74763(8) 0.1033(5) Uani d . 1 . . Cl Cl3 0.92117(5) 1.0757(2) 0.85352(11) 0.1113(5) Uani d . 1 . . C C1 0.71845(14) 0.7260(8) 0.8364(4) 0.0938(15) Uani d . 1 . . H H1A 0.7042 0.6511 0.8729 0.113 Uiso calc R 1 . . H H1B 0.6948 0.7255 0.7706 0.113 Uiso calc R 1 . . C C2 0.72877(12) 0.9365(7) 0.8709(3) 0.0711(10) Uani d . 1 . . H H2A 0.7194 1.0313 0.8183 0.085 Uiso calc R 1 . . H H2B 0.7106 0.9706 0.9083 0.085 Uiso calc R 1 . . C C3 0.80508(19) 1.1372(7) 0.9668(5) 0.1112(19) Uani d . 1 . . H H3A 0.7956 1.1811 1.0159 0.167 Uiso calc R 1 . . H H3B 0.7951 1.2379 0.9174 0.167 Uiso calc R 1 . . H H3C 0.8403 1.1203 0.9926 0.167 Uiso calc R 1 . . C C5 0.96938(15) 0.3368(8) 1.0938(4) 0.1042(17) Uani d . 1 . . H H5A 0.9898 0.4342 1.1394 0.156 Uiso calc R 1 . . H H5B 0.9796 0.3265 1.0429 0.156 Uiso calc R 1 . . H H5C 0.9725 0.2059 1.1236 0.156 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0455(4) 0.0562(5) 0.0515(5) 0.0042(3) 0.0256(4) -0.0012(4) P2 0.0471(4) 0.0723(6) 0.0446(5) 0.0019(4) 0.0218(4) 0.0110(4) P3 0.0505(4) 0.0857(6) 0.0433(5) 0.0055(4) 0.0267(4) 0.0109(4) N1 0.0510(14) 0.0775(19) 0.0600(18) 0.0070(13) 0.0323(13) 0.0150(14) N2 0.0443(13) 0.113(2) 0.0536(18) 0.0093(14) 0.0252(13) 0.0235(16) N3 0.0543(15) 0.097(2) 0.0532(18) 0.0197(15) 0.0281(14) 0.0214(16) N4 0.0528(14) 0.0605(17) 0.083(2) 0.0038(12) 0.0341(15) -0.0104(15) O1 0.0562(13) 0.0758(16) 0.0832(19) -0.0042(11) 0.0267(12) -0.0208(14) O2 0.0575(13) 0.0804(17) 0.0774(18) 0.0061(12) 0.0289(12) 0.0237(14) Cl1 0.1103(9) 0.1252(10) 0.0592(7) -0.0274(7) 0.0246(6) -0.0145(6) Cl2 0.0741(6) 0.1828(13) 0.0628(7) 0.0097(7) 0.0383(5) -0.0248(7) Cl3 0.1165(10) 0.1129(10) 0.1163(11) -0.0218(8) 0.0600(8) 0.0277(8) C1 0.0469(19) 0.130(4) 0.099(4) -0.001(2) 0.024(2) -0.030(3) C2 0.0564(19) 0.094(3) 0.070(3) 0.0203(18) 0.0339(18) 0.013(2) C3 0.105(3) 0.069(3) 0.175(6) -0.006(2) 0.073(4) -0.032(3) C5 0.068(2) 0.120(4) 0.122(5) 0.026(3) 0.036(3) 0.042(3) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.572(3) ? P1 N1 . 1.588(3) ? P1 N3 . 1.598(3) ? P1 N4 . 1.624(3) ? P2 N1 . 1.558(3) ? P2 O2 . 1.562(3) ? P2 N2 . 1.584(3) ? P2 Cl1 . 2.0165(15) ? P3 N3 . 1.555(3) ? P3 N2 . 1.564(3) ? P3 Cl2 . 1.9899(14) ? P3 Cl3 . 1.9969(16) ? N4 C3 . 1.438(5) ? N4 C2 . 1.449(4) ? O1 C1 . 1.455(4) ? O2 C5 . 1.420(5) ? C1 C2 . 1.465(6) ? C1 H1A . 0.97 ? C1 H1B . 0.97 ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 H3A . 0.96 ? C3 H3B . 0.96 ? C3 H3C . 0.96 ? C5 H5A . 0.96 ? C5 H5B . 0.96 ? C5 H5C . 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N1 . . 109.96(16) ? O1 P1 N3 . . 109.60(17) ? N1 P1 N3 . . 113.66(14) ? O1 P1 N4 . . 96.89(14) ? N1 P1 N4 . . 112.30(17) ? N3 P1 N4 . . 113.14(17) ? N1 P2 O2 . . 107.84(14) ? N1 P2 N2 . . 118.79(15) ? O2 P2 N2 . . 111.04(16) ? N1 P2 Cl1 . . 109.11(13) ? O2 P2 Cl1 . . 102.19(12) ? N2 P2 Cl1 . . 106.59(14) ? N3 P3 N2 . . 119.81(15) ? N3 P3 Cl2 . . 109.23(13) ? N2 P3 Cl2 . . 108.78(14) ? N3 P3 Cl3 . . 109.22(14) ? N2 P3 Cl3 . . 108.12(14) ? Cl2 P3 Cl3 . . 99.82(7) ? P2 N1 P1 . . 123.94(17) ? P3 N2 P2 . . 119.22(16) ? P3 N3 P1 . . 123.72(18) ? C3 N4 C2 . . 120.7(3) ? C3 N4 P1 . . 121.6(3) ? C2 N4 P1 . . 111.5(2) ? C1 O1 P1 . . 111.9(2) ? C5 O2 P2 . . 121.9(3) ? O1 C1 C2 . . 109.6(3) ? O1 C1 H1A . . 109.8 ? C2 C1 H1A . . 109.8 ? O1 C1 H1B . . 109.8 ? C2 C1 H1B . . 109.8 ? H1A C1 H1B . . 108.2 ? N4 C2 C1 . . 105.9(3) ? N4 C2 H2A . . 110.5 ? C1 C2 H2A . . 110.5 ? N4 C2 H2B . . 110.5 ? C1 C2 H2B . . 110.5 ? H2A C2 H2B . . 108.7 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O2 C5 H5A . . 109.5 ? O2 C5 H5B . . 109.5 ? H5A C5 H5B . . 109.5 ? O2 C5 H5C . . 109.5 ? H5A C5 H5C . . 109.5 ? H5B C5 H5C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 P2 N1 P1 . . . . -138.7(2) ? N2 P2 N1 P1 . . . . -11.3(3) ? Cl1 P2 N1 P1 . . . . 111.1(2) ? O1 P1 N1 P2 . . . . 132.0(2) ? N3 P1 N1 P2 . . . . 8.7(3) ? N4 P1 N1 P2 . . . . -121.3(2) ? N3 P3 N2 P2 . . . . -3.9(4) ? Cl2 P3 N2 P2 . . . . -130.5(2) ? Cl3 P3 N2 P2 . . . . 122.0(2) ? N1 P2 N2 P3 . . . . 8.4(3) ? O2 P2 N2 P3 . . . . 134.3(2) ? Cl1 P2 N2 P3 . . . . -115.2(2) ? N2 P3 N3 P1 . . . . 1.8(4) ? Cl2 P3 N3 P1 . . . . 128.2(2) ? Cl3 P3 N3 P1 . . . . -123.6(2) ? O1 P1 N3 P3 . . . . -127.3(2) ? N1 P1 N3 P3 . . . . -3.9(3) ? N4 P1 N3 P3 . . . . 125.8(2) ? O1 P1 N4 C3 . . . . -167.8(4) ? N1 P1 N4 C3 . . . . 77.3(4) ? N3 P1 N4 C3 . . . . -53.0(5) ? O1 P1 N4 C2 . . . . -15.4(3) ? N1 P1 N4 C2 . . . . -130.3(3) ? N3 P1 N4 C2 . . . . 99.4(3) ? N1 P1 O1 C1 . . . . 120.5(3) ? N3 P1 O1 C1 . . . . -113.9(3) ? N4 P1 O1 C1 . . . . 3.7(3) ? N1 P2 O2 C5 . . . . -176.8(4) ? N2 P2 O2 C5 . . . . 51.5(4) ? Cl1 P2 O2 C5 . . . . -61.9(4) ? P1 O1 C1 C2 . . . . 8.6(5) ? C3 N4 C2 C1 . . . . 174.1(5) ? P1 N4 C2 C1 . . . . 21.5(4) ? O1 C1 C2 N4 . . . . -18.4(5) ? #===END data_ETE2c _database_code_depnum_ccdc_archive 'CCDC 865162' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common cyclophosphazene _chemical_formula_moiety ? _chemical_formula_sum 'C5 H13 Cl2 N4 O3 P3' _chemical_formula_iupac ? _chemical_formula_weight 341.00 _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.6889(6) _cell_length_b 11.8941(8) _cell_length_c 26.4305(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2731.5(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9978 _cell_measurement_theta_min 2.8056 _cell_measurement_theta_max 28.2573 _cell_measurement_temperature 120.(2) _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.240 _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.83 _exptl_special_details ; ; _diffrn_ambient_temperature 120.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 13156 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _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. ; _reflns_number_total 2406 _reflns_number_gt 2321 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.0699 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _refine_ls_number_reflns 2406 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+3.7894P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.372 _refine_diff_density_min -0.353 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 1.03709(6) 0.86882(5) 0.424729(19) 0.01587(14) Uani d . 1 . . P P2 0.75799(6) 0.91349(5) 0.376359(19) 0.01680(14) Uani d . 1 . . P P3 0.99881(6) 0.83617(5) 0.321015(19) 0.01507(14) Uani d . 1 . . N N1 0.8624(2) 0.91067(15) 0.42487(6) 0.0193(4) Uani d . 1 . . N N2 0.8215(2) 0.86437(16) 0.32465(6) 0.0198(4) Uani d . 1 . . N N3 1.0932(2) 0.81919(16) 0.37134(6) 0.0184(4) Uani d . 1 . . N N4 1.1534(2) 0.96409(16) 0.44849(7) 0.0236(4) Uani d . 1 . . O O1 1.06438(18) 0.77653(13) 0.46707(5) 0.0238(4) Uani d . 1 . . O O2 0.59950(17) 0.85819(15) 0.38989(6) 0.0267(4) Uani d . 1 . . O O3 1.01277(17) 0.73333(13) 0.28415(5) 0.0193(3) Uani d . 1 . . Cl Cl1 0.69798(8) 1.07578(5) 0.36328(2) 0.03609(17) Uani d . 1 . . Cl Cl2 1.10301(7) 0.96005(5) 0.28019(2) 0.02848(15) Uani d . 1 . . C C1 1.1654(3) 0.8188(2) 0.50739(8) 0.0310(6) Uani d . 1 . . H H1A 1.2323 0.7578 0.5203 0.037 Uiso calc R 1 . . H H1B 1.1037 0.8488 0.5358 0.037 Uiso calc R 1 . . C C2 1.2612(3) 0.9108(2) 0.48393(8) 0.0299(6) Uani d . 1 . . H H2A 1.2971 0.9649 0.5098 0.036 Uiso calc R 1 . . H H2B 1.3515 0.8795 0.4659 0.036 Uiso calc R 1 . . C C3 1.2052(3) 1.0600(2) 0.41899(10) 0.0359(6) Uani d . 1 . . H H3A 1.2313 1.1221 0.4418 0.054 Uiso calc R 1 . . H H3B 1.123 1.0837 0.396 0.054 Uiso calc R 1 . . H H3C 1.2963 1.0389 0.3993 0.054 Uiso calc R 1 . . C C4 0.4864(3) 0.8382(3) 0.35033(10) 0.0401(7) Uani d . 1 . . H H4A 0.4674 0.9083 0.3319 0.06 Uiso calc R 1 . . H H4B 0.3902 0.8118 0.3656 0.06 Uiso calc R 1 . . H H4C 0.5255 0.7811 0.3269 0.06 Uiso calc R 1 . . C C5 1.1613(3) 0.6845(2) 0.27372(9) 0.0289(5) Uani d . 1 . . H H5A 1.2259 0.7396 0.2562 0.043 Uiso calc R 1 . . H H5B 1.1484 0.6179 0.2523 0.043 Uiso calc R 1 . . H H5C 1.2106 0.6628 0.3056 0.043 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0152(3) 0.0181(3) 0.0143(3) 0.0012(2) -0.0010(2) -0.0001(2) P2 0.0144(3) 0.0197(3) 0.0163(3) 0.0035(2) 0.0006(2) 0.0003(2) P3 0.0133(3) 0.0175(3) 0.0144(3) -0.0010(2) 0.0015(2) -0.0006(2) N1 0.0178(9) 0.0239(10) 0.0163(8) 0.0039(8) 0.0013(7) -0.0011(7) N2 0.0141(9) 0.0291(10) 0.0162(9) 0.0018(8) -0.0016(7) -0.0020(7) N3 0.0134(9) 0.0241(10) 0.0177(9) 0.0025(7) 0.0001(7) -0.0027(7) N4 0.0221(10) 0.0290(10) 0.0198(9) -0.0048(8) -0.0045(8) -0.0037(8) O1 0.0271(9) 0.0248(8) 0.0196(8) 0.0045(7) -0.0030(6) 0.0046(6) O2 0.0150(8) 0.0431(10) 0.0219(8) 0.0007(7) 0.0022(6) 0.0011(7) O3 0.0192(8) 0.0216(8) 0.0173(7) -0.0028(6) 0.0006(6) -0.0044(6) Cl1 0.0481(4) 0.0251(3) 0.0350(3) 0.0150(3) -0.0067(3) 0.0028(2) Cl2 0.0347(3) 0.0247(3) 0.0261(3) -0.0092(2) 0.0062(2) 0.0031(2) C1 0.0303(13) 0.0464(15) 0.0164(11) 0.0142(12) -0.0066(10) -0.0016(10) C2 0.0203(12) 0.0465(15) 0.0229(11) 0.0074(11) -0.0059(10) -0.0125(11) C3 0.0377(15) 0.0283(13) 0.0416(14) -0.0122(12) 0.0012(12) -0.0040(11) C4 0.0172(12) 0.069(2) 0.0336(14) -0.0081(13) -0.0026(10) -0.0055(13) C5 0.0274(13) 0.0296(13) 0.0297(12) 0.0073(10) -0.0013(10) -0.0082(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.5854(15) ? P1 N1 . 1.5972(18) ? P1 N3 . 1.6054(17) ? P1 N4 . 1.6433(19) ? P2 O2 . 1.5675(16) ? P2 N1 . 1.5712(18) ? P2 N2 . 1.5856(18) ? P2 Cl1 . 2.0291(8) ? P3 O3 . 1.5686(15) ? P3 N3 . 1.5755(17) ? P3 N2 . 1.5793(18) ? P3 Cl2 . 2.0383(8) ? N4 C3 . 1.453(3) ? N4 C2 . 1.468(3) ? O1 C1 . 1.470(3) ? O2 C4 . 1.454(3) ? O3 C5 . 1.442(3) ? C1 C2 . 1.508(4) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 H4A . 0.98 ? C4 H4B . 0.98 ? C4 H4C . 0.98 ? C5 H5A . 0.98 ? C5 H5B . 0.98 ? C5 H5C . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N1 . . 110.87(9) ? O1 P1 N3 . . 108.69(9) ? N1 P1 N3 . . 113.90(9) ? O1 P1 N4 . . 96.64(9) ? N1 P1 N4 . . 111.64(10) ? N3 P1 N4 . . 113.75(10) ? O2 P2 N1 . . 108.20(9) ? O2 P2 N2 . . 110.36(9) ? N1 P2 N2 . . 119.63(10) ? O2 P2 Cl1 . . 102.25(7) ? N1 P2 Cl1 . . 107.92(7) ? N2 P2 Cl1 . . 107.05(8) ? O3 P3 N3 . . 112.59(9) ? O3 P3 N2 . . 106.19(9) ? N3 P3 N2 . . 118.91(9) ? O3 P3 Cl2 . . 101.57(6) ? N3 P3 Cl2 . . 107.97(7) ? N2 P3 Cl2 . . 108.17(8) ? P2 N1 P1 . . 123.60(11) ? P3 N2 P2 . . 118.06(11) ? P3 N3 P1 . . 122.48(11) ? C3 N4 C2 . . 118.9(2) ? C3 N4 P1 . . 121.78(16) ? C2 N4 P1 . . 109.79(16) ? C1 O1 P1 . . 111.36(14) ? C4 O2 P2 . . 119.87(15) ? C5 O3 P3 . . 120.14(13) ? O1 C1 C2 . . 106.25(17) ? O1 C1 H1A . . 110.5 ? C2 C1 H1A . . 110.5 ? O1 C1 H1B . . 110.5 ? C2 C1 H1B . . 110.5 ? H1A C1 H1B . . 108.7 ? N4 C2 C1 . . 102.91(19) ? N4 C2 H2A . . 111.2 ? C1 C2 H2A . . 111.2 ? N4 C2 H2B . . 111.2 ? C1 C2 H2B . . 111.2 ? H2A C2 H2B . . 109.1 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O2 C4 H4A . . 109.5 ? O2 C4 H4B . . 109.5 ? H4A C4 H4B . . 109.5 ? O2 C4 H4C . . 109.5 ? H4A C4 H4C . . 109.5 ? H4B C4 H4C . . 109.5 ? O3 C5 H5A . . 109.5 ? O3 C5 H5B . . 109.5 ? H5A C5 H5B . . 109.5 ? O3 C5 H5C . . 109.5 ? H5A C5 H5C . . 109.5 ? H5B C5 H5C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 P2 N1 P1 . . . . 132.23(13) ? N2 P2 N1 P1 . . . . 4.75(19) ? Cl1 P2 N1 P1 . . . . -117.83(12) ? O1 P1 N1 P2 . . . . -128.09(13) ? N3 P1 N1 P2 . . . . -5.13(18) ? N4 P1 N1 P2 . . . . 125.39(14) ? O3 P3 N2 P2 . . . . 147.98(12) ? N3 P3 N2 P2 . . . . 19.86(18) ? Cl2 P3 N2 P2 . . . . -103.65(12) ? O2 P2 N2 P3 . . . . -138.33(12) ? N1 P2 N2 P3 . . . . -11.86(18) ? Cl1 P2 N2 P3 . . . . 111.15(11) ? O3 P3 N3 P1 . . . . -146.56(12) ? N2 P3 N3 P1 . . . . -21.48(18) ? Cl2 P3 N3 P1 . . . . 102.14(12) ? O1 P1 N3 P3 . . . . 137.64(13) ? N1 P1 N3 P3 . . . . 13.50(17) ? N4 P1 N3 P3 . . . . -115.97(14) ? O1 P1 N4 C3 . . . . 164.86(19) ? N1 P1 N4 C3 . . . . -79.5(2) ? N3 P1 N4 C3 . . . . 51.1(2) ? O1 P1 N4 C2 . . . . 19.01(16) ? N1 P1 N4 C2 . . . . 134.60(15) ? N3 P1 N4 C2 . . . . -94.80(16) ? N1 P1 O1 C1 . . . . -112.25(15) ? N3 P1 O1 C1 . . . . 121.82(15) ? N4 P1 O1 C1 . . . . 3.96(16) ? N1 P2 O2 C4 . . . . -173.16(19) ? N2 P2 O2 C4 . . . . -40.5(2) ? Cl1 P2 O2 C4 . . . . 73.08(19) ? N3 P3 O3 C5 . . . . -46.56(18) ? N2 P3 O3 C5 . . . . -178.32(16) ? Cl2 P3 O3 C5 . . . . 68.66(16) ? P1 O1 C1 C2 . . . . -24.7(2) ? C3 N4 C2 C1 . . . . 178.8(2) ? P1 N4 C2 C1 . . . . -34.2(2) ? O1 C1 C2 N4 . . . . 35.8(2) ? #===END data_ETE3a _database_code_depnum_ccdc_archive 'CCDC 865163' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common 309_494_A _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl3 N4 O2 P3' _chemical_formula_iupac ? _chemical_formula_weight 407.49 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.8585(2) _cell_length_b 11.5296(3) _cell_length_c 16.1551(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1650.00(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6339 _cell_measurement_theta_min 2.1701 _cell_measurement_theta_max 28.2486 _cell_measurement_temperature 296.(2) _exptl_crystal_description prisma _exptl_crystal_colour colourless _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.320 _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.77 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 8342 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 9 _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. ; _reflns_number_total 3918 _reflns_number_gt 3769 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.0722 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_number_reflns 3918 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.1756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.211 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(6) 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' Cl Cl 0.1484 0.1585 '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' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.25356(5) 0.24636(4) 0.08894(2) 0.03836(11) Uani d . 1 . . P P2 0.13498(5) 0.27339(4) 0.24739(3) 0.03684(11) Uani d . 1 . . P P3 0.39439(5) 0.15229(4) 0.22705(3) 0.03553(10) Uani d . 1 . . N N1 0.11928(19) 0.27724(16) 0.15101(9) 0.0477(4) Uani d . 1 . . N N2 0.27663(18) 0.20964(16) 0.28678(9) 0.0441(4) Uani d . 1 . . N N3 0.39418(19) 0.18480(15) 0.13326(9) 0.0471(4) Uani d . 1 . . N N4 0.3094(2) 0.35215(16) 0.03055(10) 0.0504(4) Uani d . 1 . . O O1 0.19018(18) 0.16699(14) 0.01732(8) 0.0522(4) Uani d . 1 . . O O2 -0.01691(15) 0.22164(13) 0.28298(8) 0.0459(3) Uani d . 1 . . Cl Cl1 0.13453(8) 0.43606(5) 0.29263(4) 0.06612(16) Uani d . 1 . . Cl Cl2 0.60067(5) 0.17930(4) 0.27254(3) 0.04979(12) Uani d . 1 . . Cl Cl3 0.37987(9) -0.02125(5) 0.23946(4) 0.07141(18) Uani d . 1 . . C C1 0.2395(3) 0.2073(2) -0.06335(11) 0.0541(5) Uani d . 1 . . H H1A 0.1599 0.1961 -0.1038 0.065 Uiso calc R 1 . . H H1B 0.3276 0.1641 -0.0811 0.065 Uiso calc R 1 . . C C2 0.2772(2) 0.3342(2) -0.05612(11) 0.0490(5) Uani d . 1 . . H H2A 0.3643 0.3533 -0.0898 0.059 Uiso calc R 1 . . H H2B 0.1926 0.3816 -0.0736 0.059 Uiso calc R 1 . . C C3 0.3673(3) 0.46105(19) 0.06068(16) 0.0611(6) Uani d . 1 . . H H3A 0.462 0.4775 0.0343 0.092 Uiso calc R 1 . . H H3B 0.3819 0.4564 0.1195 0.092 Uiso calc R 1 . . H H3C 0.2967 0.5218 0.0484 0.092 Uiso calc R 1 . . C C4 -0.0313(2) 0.19806(18) 0.36937(11) 0.0418(4) Uani d . 1 . . C C5 0.0262(3) 0.09654(19) 0.40026(14) 0.0523(5) Uani d . 1 . . H H5 0.0738 0.0433 0.3658 0.063 Uiso calc R 1 . . C C6 0.0112(3) 0.0754(2) 0.48504(16) 0.0615(6) Uani d . 1 . . H H6 0.0519 0.0083 0.5079 0.074 Uiso calc R 1 . . C C7 -0.0631(3) 0.1532(2) 0.53481(14) 0.0613(6) Uani d . 1 . . H H7 -0.0731 0.1384 0.5911 0.074 Uiso calc R 1 . . C C8 -0.1224(3) 0.2521(3) 0.50172(16) 0.0678(6) Uani d . 1 . . H H8 -0.1737 0.3039 0.5357 0.081 Uiso calc R 1 . . C C9 -0.1070(3) 0.2763(2) 0.41740(14) 0.0587(5) Uani d . 1 . . H H9 -0.147 0.3437 0.3947 0.07 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0406(2) 0.0500(2) 0.02445(17) -0.0005(2) -0.00372(16) 0.00182(17) P2 0.0344(2) 0.0494(3) 0.02668(18) 0.00176(17) -0.00195(16) -0.00139(16) P3 0.0375(2) 0.0400(2) 0.02911(19) 0.00184(17) -0.00354(16) 0.00332(16) N1 0.0391(8) 0.0748(11) 0.0294(7) 0.0091(8) -0.0056(6) 0.0038(7) N2 0.0399(8) 0.0678(11) 0.0246(6) 0.0059(7) -0.0027(6) 0.0030(7) N3 0.0458(8) 0.0660(10) 0.0295(7) 0.0128(8) 0.0037(6) 0.0045(7) N4 0.0641(11) 0.0538(9) 0.0332(7) -0.0107(8) -0.0069(7) 0.0049(7) O1 0.0646(9) 0.0610(8) 0.0309(6) -0.0139(7) -0.0039(6) -0.0025(6) O2 0.0374(6) 0.0669(9) 0.0333(6) -0.0059(6) 0.0003(5) -0.0041(6) Cl1 0.0844(4) 0.0503(3) 0.0637(3) -0.0017(3) 0.0034(3) -0.0111(2) Cl2 0.0387(2) 0.0558(3) 0.0549(3) 0.0031(2) -0.01147(19) 0.0045(2) Cl3 0.0985(5) 0.0411(2) 0.0746(4) -0.0094(3) -0.0144(4) 0.0035(2) C1 0.0674(13) 0.0668(13) 0.0281(8) 0.0035(11) -0.0032(9) -0.0023(8) C2 0.0558(12) 0.0609(12) 0.0304(8) 0.0065(10) 0.0005(8) 0.0078(8) C3 0.0635(14) 0.0488(11) 0.0709(14) -0.0015(10) -0.0122(12) -0.0017(10) C4 0.0336(8) 0.0599(11) 0.0320(8) -0.0059(8) 0.0030(7) -0.0030(8) C5 0.0583(12) 0.0501(11) 0.0484(11) -0.0048(9) 0.0124(10) -0.0017(9) C6 0.0651(14) 0.0643(14) 0.0551(13) -0.0057(12) 0.0099(11) 0.0126(11) C7 0.0599(13) 0.0847(16) 0.0392(10) -0.0127(12) 0.0084(10) 0.0022(11) C8 0.0688(15) 0.0866(14) 0.0479(10) 0.0059(14) 0.0190(11) -0.0127(12) C9 0.0540(12) 0.0734(14) 0.0486(11) 0.0122(11) 0.0098(10) -0.0001(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.5785(14) ? P1 N1 . 1.5960(17) ? P1 N3 . 1.6025(17) ? P1 N4 . 1.6192(18) ? P2 N1 . 1.5639(15) ? P2 O2 . 1.5802(14) ? P2 N2 . 1.5873(16) ? P2 Cl1 . 2.0130(7) ? P3 N3 . 1.5609(15) ? P3 N2 . 1.5673(16) ? P3 Cl2 . 1.9941(6) ? P3 Cl3 . 2.0149(7) ? N4 C3 . 1.441(3) ? N4 C2 . 1.444(2) ? O1 C1 . 1.451(2) ? O2 C4 . 1.428(2) ? C1 C2 . 1.504(3) ? C1 H1A . 0.97 ? C1 H1B . 0.97 ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 H3A . 0.96 ? C3 H3B . 0.96 ? C3 H3C . 0.96 ? C4 C9 . 1.365(3) ? C4 C5 . 1.371(3) ? C5 C6 . 1.397(3) ? C5 H5 . 0.93 ? C6 C7 . 1.372(4) ? C6 H6 . 0.93 ? C7 C8 . 1.365(4) ? C7 H7 . 0.93 ? C8 C9 . 1.397(3) ? C8 H8 . 0.93 ? C9 H9 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N1 . . 108.95(9) ? O1 P1 N3 . . 110.32(9) ? N1 P1 N3 . . 113.42(8) ? O1 P1 N4 . . 96.79(8) ? N1 P1 N4 . . 115.19(10) ? N3 P1 N4 . . 110.88(9) ? N1 P2 O2 . . 107.29(8) ? N1 P2 N2 . . 118.85(8) ? O2 P2 N2 . . 110.64(8) ? N1 P2 Cl1 . . 109.57(7) ? O2 P2 Cl1 . . 102.59(6) ? N2 P2 Cl1 . . 106.71(7) ? N3 P3 N2 . . 119.71(9) ? N3 P3 Cl2 . . 108.74(7) ? N2 P3 Cl2 . . 108.49(6) ? N3 P3 Cl3 . . 109.57(7) ? N2 P3 Cl3 . . 108.38(7) ? Cl2 P3 Cl3 . . 100.19(3) ? P2 N1 P1 . . 123.56(10) ? P3 N2 P2 . . 118.34(9) ? P3 N3 P1 . . 122.75(10) ? C3 N4 C2 . . 121.53(19) ? C3 N4 P1 . . 124.63(15) ? C2 N4 P1 . . 113.35(15) ? C1 O1 P1 . . 111.43(13) ? C4 O2 P2 . . 120.25(11) ? O1 C1 C2 . . 107.98(16) ? O1 C1 H1A . . 110.1 ? C2 C1 H1A . . 110.1 ? O1 C1 H1B . . 110.1 ? C2 C1 H1B . . 110.1 ? H1A C1 H1B . . 108.4 ? N4 C2 C1 . . 105.00(17) ? N4 C2 H2A . . 110.7 ? C1 C2 H2A . . 110.7 ? N4 C2 H2B . . 110.7 ? C1 C2 H2B . . 110.7 ? H2A C2 H2B . . 108.8 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? C9 C4 C5 . . 122.65(19) ? C9 C4 O2 . . 118.28(19) ? C5 C4 O2 . . 119.03(18) ? C4 C5 C6 . . 118.0(2) ? C4 C5 H5 . . 121.0 ? C6 C5 H5 . . 121.0 ? C7 C6 C5 . . 120.4(2) ? C7 C6 H6 . . 119.8 ? C5 C6 H6 . . 119.8 ? C8 C7 C6 . . 120.1(2) ? C8 C7 H7 . . 120.0 ? C6 C7 H7 . . 120.0 ? C7 C8 C9 . . 120.8(2) ? C7 C8 H8 . . 119.6 ? C9 C8 H8 . . 119.6 ? C4 C9 C8 . . 118.0(2) ? C4 C9 H9 . . 121.0 ? C8 C9 H9 . . 121.0 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 P2 N1 P1 . . . . -140.59(13) ? N2 P2 N1 P1 . . . . -14.22(18) ? Cl1 P2 N1 P1 . . . . 108.74(12) ? O1 P1 N1 P2 . . . . 135.85(13) ? N3 P1 N1 P2 . . . . 12.57(18) ? N4 P1 N1 P2 . . . . -116.71(13) ? N3 P3 N2 P2 . . . . 15.56(17) ? Cl2 P3 N2 P2 . . . . 141.07(9) ? Cl3 P3 N2 P2 . . . . -111.02(11) ? N1 P2 N2 P3 . . . . -0.46(17) ? O2 P2 N2 P3 . . . . 124.30(11) ? Cl1 P2 N2 P3 . . . . -124.83(10) ? N2 P3 N3 P1 . . . . -17.37(18) ? Cl2 P3 N3 P1 . . . . -142.76(11) ? Cl3 P3 N3 P1 . . . . 108.65(12) ? O1 P1 N3 P3 . . . . -119.21(13) ? N1 P1 N3 P3 . . . . 3.32(17) ? N4 P1 N3 P3 . . . . 134.75(13) ? O1 P1 N4 C3 . . . . 173.7(2) ? N1 P1 N4 C3 . . . . 59.1(2) ? N3 P1 N4 C3 . . . . -71.5(2) ? O1 P1 N4 C2 . . . . 1.63(17) ? N1 P1 N4 C2 . . . . -113.04(16) ? N3 P1 N4 C2 . . . . 116.45(16) ? N1 P1 O1 C1 . . . . 132.82(15) ? N3 P1 O1 C1 . . . . -102.06(15) ? N4 P1 O1 C1 . . . . 13.21(16) ? N1 P2 O2 C4 . . . . 174.54(15) ? N2 P2 O2 C4 . . . . 43.45(17) ? Cl1 P2 O2 C4 . . . . -70.06(15) ? P1 O1 C1 C2 . . . . -23.5(2) ? C3 N4 C2 C1 . . . . 172.8(2) ? P1 N4 C2 C1 . . . . -14.9(2) ? O1 C1 C2 N4 . . . . 23.1(2) ? P2 O2 C4 C9 . . . . 100.3(2) ? P2 O2 C4 C5 . . . . -81.9(2) ? C9 C4 C5 C6 . . . . -2.6(3) ? O2 C4 C5 C6 . . . . 179.8(2) ? C4 C5 C6 C7 . . . . 1.9(4) ? C5 C6 C7 C8 . . . . -0.3(4) ? C6 C7 C8 C9 . . . . -0.8(4) ? C5 C4 C9 C8 . . . . 1.5(4) ? O2 C4 C9 C8 . . . . 179.2(2) ? C7 C8 C9 C4 . . . . 0.2(4) ? #===END data_ETE3c _database_code_depnum_ccdc_archive 'CCDC 865164' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common cyclophosphazene _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl2 N4 O3 P3' _chemical_formula_iupac ? _chemical_formula_weight 465.14 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0419(6) _cell_length_b 20.6060(11) _cell_length_c 8.0388(5) _cell_angle_alpha 90 _cell_angle_beta 97.795(3) _cell_angle_gamma 90 _cell_volume 1976.28(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8957 _cell_measurement_theta_min 2.6120 _cell_measurement_theta_max 28.2446 _cell_measurement_temperature 120.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.070 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 120.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 14958 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _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. ; _reflns_number_total 3485 _reflns_number_gt 3163 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.0851 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_number_reflns 3485 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+1.6712P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.483 _refine_diff_density_min -0.430 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.89239(4) 0.00795(2) 0.74793(7) 0.01696(14) Uani d . 1 . . P P2 0.90944(4) 0.14145(2) 0.79885(7) 0.01712(14) Uani d . 1 . . P P3 0.73918(4) 0.07596(2) 0.91104(7) 0.01829(14) Uani d . 1 . . N N1 0.94935(14) 0.07659(8) 0.7247(2) 0.0195(4) Uani d . 1 . . N N2 0.81068(14) 0.14055(8) 0.9098(2) 0.0216(4) Uani d . 1 . . N N3 0.78915(14) 0.01069(8) 0.8546(2) 0.0204(4) Uani d . 1 . . N N4 0.86153(15) -0.02901(8) 0.5670(2) 0.0222(4) Uani d . 1 . . O O1 0.97990(12) -0.04424(7) 0.83042(19) 0.0218(3) Uani d . 1 . . O O2 1.00949(11) 0.17893(7) 0.90640(18) 0.0198(3) Uani d . 1 . . O O3 0.70247(12) 0.06366(7) 1.08943(19) 0.0232(3) Uani d . 1 . . Cl Cl1 0.86882(4) 0.20293(3) 0.60373(7) 0.02772(15) Uani d . 1 . . Cl Cl2 0.58976(4) 0.09289(3) 0.76736(8) 0.03010(15) Uani d . 1 . . C C1 0.99785(18) -0.09508(10) 0.7102(3) 0.0232(5) Uani d . 1 . . H H1A 1.0107 -0.1374 0.7678 0.028 Uiso calc R 1 . . H H1B 1.0637 -0.0848 0.6535 0.028 Uiso calc R 1 . . C C2 0.89254(18) -0.09734(10) 0.5842(3) 0.0226(5) Uani d . 1 . . H H2A 0.9077 -0.1158 0.4759 0.027 Uiso calc R 1 . . H H2B 0.8331 -0.1231 0.6272 0.027 Uiso calc R 1 . . C C3 0.7644(2) -0.01006(12) 0.4496(3) 0.0331(6) Uani d . 1 . . H H3A 0.7777 -0.0203 0.3349 0.05 Uiso calc R 1 . . H H3B 0.7517 0.0367 0.4592 0.05 Uiso calc R 1 . . H H3C 0.6983 -0.0338 0.4755 0.05 Uiso calc R 1 . . C C4 1.11747(16) 0.17951(10) 0.8562(3) 0.0177(4) Uani d . 1 . . C C5 1.14672(17) 0.23012(10) 0.7582(3) 0.0222(5) Uani d . 1 . . H H5 1.0942 0.2631 0.7206 0.027 Uiso calc R 1 . . C C6 1.25509(17) 0.23152(10) 0.7160(3) 0.0258(5) Uani d . 1 . . H H6 1.2773 0.2658 0.6488 0.031 Uiso calc R 1 . . C C7 1.33051(17) 0.18292(11) 0.7719(3) 0.0261(5) Uani d . 1 . . H H7 1.4044 0.184 0.7428 0.031 Uiso calc R 1 . . C C8 1.29873(18) 0.13262(10) 0.8702(3) 0.0256(5) Uani d . 1 . . H H8 1.351 0.0996 0.9085 0.031 Uiso calc R 1 . . C C9 1.19089(18) 0.13046(10) 0.9127(3) 0.0219(5) Uani d . 1 . . H H9 1.1682 0.096 0.9791 0.026 Uiso calc R 1 . . C C10 0.63510(17) 0.10520(11) 1.1719(3) 0.0237(5) Uani d . 1 . . C C11 0.6723(2) 0.16596(12) 1.2229(3) 0.0323(5) Uani d . 1 . . H H11 0.7415 0.1822 1.196 0.039 Uiso calc R 1 . . C C12 0.6059(3) 0.20312(14) 1.3150(4) 0.0455(7) Uani d . 1 . . H H12 0.6296 0.2454 1.3513 0.055 Uiso calc R 1 . . C C13 0.5061(3) 0.17900(17) 1.3539(4) 0.0508(8) Uani d . 1 . . H H13 0.4616 0.2045 1.4179 0.061 Uiso calc R 1 . . C C14 0.4702(2) 0.11771(17) 1.3000(4) 0.0499(8) Uani d . 1 . . H H14 0.4009 0.1014 1.3265 0.06 Uiso calc R 1 . . C C15 0.5345(2) 0.08020(13) 1.2080(3) 0.0360(6) Uani d . 1 . . H H15 0.5103 0.0382 1.1702 0.043 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0202(3) 0.0135(3) 0.0165(3) 0.00072(19) 0.0003(2) -0.0004(2) P2 0.0184(3) 0.0135(3) 0.0196(3) -0.00077(19) 0.0030(2) -0.0006(2) P3 0.0171(3) 0.0163(3) 0.0214(3) 0.00022(19) 0.0026(2) 0.0023(2) N1 0.0216(8) 0.0166(8) 0.0209(9) -0.0014(7) 0.0053(7) -0.0019(7) N2 0.0227(9) 0.0156(8) 0.0276(10) 0.0007(7) 0.0073(8) -0.0025(8) N3 0.0219(8) 0.0154(8) 0.0236(10) -0.0009(7) 0.0022(7) 0.0019(7) N4 0.0293(9) 0.0165(8) 0.0193(10) -0.0007(7) -0.0027(8) -0.0020(8) O1 0.0256(7) 0.0190(7) 0.0197(8) 0.0055(6) -0.0011(6) -0.0026(6) O2 0.0206(7) 0.0186(7) 0.0208(8) -0.0023(5) 0.0051(6) -0.0048(6) O3 0.0254(7) 0.0229(7) 0.0223(8) 0.0031(6) 0.0071(6) 0.0052(7) Cl1 0.0291(3) 0.0243(3) 0.0287(3) 0.0020(2) 0.0004(2) 0.0095(2) Cl2 0.0216(3) 0.0336(3) 0.0328(3) 0.0046(2) -0.0045(2) 0.0033(3) C1 0.0272(11) 0.0174(10) 0.0261(12) 0.0035(8) 0.0071(9) -0.0033(9) C2 0.0305(11) 0.0154(10) 0.0224(11) -0.0029(8) 0.0047(9) -0.0032(9) C3 0.0387(13) 0.0289(12) 0.0272(13) -0.0029(10) -0.0114(11) 0.0017(11) C4 0.0187(9) 0.0175(9) 0.0163(10) -0.0021(8) 0.0006(8) -0.0048(8) C5 0.0216(10) 0.0159(10) 0.0279(13) 0.0005(8) -0.0009(9) 0.0000(9) C6 0.0232(10) 0.0227(11) 0.0310(13) -0.0049(8) 0.0020(9) 0.0063(10) C7 0.0177(10) 0.0278(11) 0.0324(13) -0.0014(8) 0.0014(9) -0.0008(10) C8 0.0233(10) 0.0208(10) 0.0304(13) 0.0030(8) -0.0044(9) -0.0011(10) C9 0.0280(11) 0.0173(10) 0.0192(11) -0.0016(8) -0.0009(9) 0.0019(9) C10 0.0218(10) 0.0303(12) 0.0191(11) 0.0068(9) 0.0027(9) 0.0062(10) C11 0.0347(12) 0.0314(12) 0.0306(13) 0.0051(10) 0.0037(11) 0.0004(11) C12 0.0586(18) 0.0432(16) 0.0345(15) 0.0202(13) 0.0056(14) -0.0027(13) C13 0.0546(17) 0.072(2) 0.0280(15) 0.0414(16) 0.0153(13) 0.0145(15) C14 0.0283(13) 0.084(2) 0.0405(17) 0.0168(14) 0.0174(12) 0.0225(17) C15 0.0286(12) 0.0462(15) 0.0345(14) -0.0018(10) 0.0089(11) 0.0096(12) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.5865(14) ? P1 N1 . 1.5939(17) ? P1 N3 . 1.6039(18) ? P1 N4 . 1.6388(18) ? P2 N1 . 1.5655(17) ? P2 N2 . 1.5806(18) ? P2 O2 . 1.5852(14) ? P2 Cl1 . 2.0238(8) ? P3 N3 . 1.5657(17) ? P3 O3 . 1.5774(16) ? P3 N2 . 1.5859(17) ? P3 Cl2 . 2.0321(7) ? N4 C3 . 1.454(3) ? N4 C2 . 1.459(3) ? O1 C1 . 1.461(2) ? O2 C4 . 1.413(2) ? O3 C10 . 1.406(3) ? C1 C2 . 1.512(3) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 C9 . 1.379(3) ? C4 C5 . 1.381(3) ? C5 C6 . 1.392(3) ? C5 H5 . 0.95 ? C6 C7 . 1.385(3) ? C6 H6 . 0.95 ? C7 C8 . 1.388(3) ? C7 H7 . 0.95 ? C8 C9 . 1.388(3) ? C8 H8 . 0.95 ? C9 H9 . 0.95 ? C10 C11 . 1.374(3) ? C10 C15 . 1.383(3) ? C11 C12 . 1.391(4) ? C11 H11 . 0.95 ? C12 C13 . 1.375(4) ? C12 H12 . 0.95 ? C13 C14 . 1.385(5) ? C13 H13 . 0.95 ? C14 C15 . 1.378(4) ? C14 H14 . 0.95 ? C15 H15 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N1 . . 112.24(9) ? O1 P1 N3 . . 108.63(9) ? N1 P1 N3 . . 114.11(9) ? O1 P1 N4 . . 96.53(8) ? N1 P1 N4 . . 110.95(10) ? N3 P1 N4 . . 113.05(9) ? N1 P2 N2 . . 119.89(9) ? N1 P2 O2 . . 111.95(9) ? N2 P2 O2 . . 105.79(9) ? N1 P2 Cl1 . . 107.07(7) ? N2 P2 Cl1 . . 108.88(7) ? O2 P2 Cl1 . . 101.75(6) ? N3 P3 O3 . . 106.96(9) ? N3 P3 N2 . . 119.26(9) ? O3 P3 N2 . . 111.09(9) ? N3 P3 Cl2 . . 109.15(7) ? O3 P3 Cl2 . . 102.04(6) ? N2 P3 Cl2 . . 106.98(7) ? P2 N1 P1 . . 123.62(11) ? P2 N2 P3 . . 117.64(11) ? P3 N3 P1 . . 122.78(11) ? C3 N4 C2 . . 119.61(18) ? C3 N4 P1 . . 121.14(15) ? C2 N4 P1 . . 109.89(14) ? C1 O1 P1 . . 111.03(13) ? C4 O2 P2 . . 120.61(12) ? C10 O3 P3 . . 125.58(13) ? O1 C1 C2 . . 106.21(16) ? O1 C1 H1A . . 110.5 ? C2 C1 H1A . . 110.5 ? O1 C1 H1B . . 110.5 ? C2 C1 H1B . . 110.5 ? H1A C1 H1B . . 108.7 ? N4 C2 C1 . . 102.38(16) ? N4 C2 H2A . . 111.3 ? C1 C2 H2A . . 111.3 ? N4 C2 H2B . . 111.3 ? C1 C2 H2B . . 111.3 ? H2A C2 H2B . . 109.2 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? C9 C4 C5 . . 122.67(19) ? C9 C4 O2 . . 118.27(18) ? C5 C4 O2 . . 119.02(17) ? C4 C5 C6 . . 118.33(19) ? C4 C5 H5 . . 120.8 ? C6 C5 H5 . . 120.8 ? C7 C6 C5 . . 120.1(2) ? C7 C6 H6 . . 120.0 ? C5 C6 H6 . . 120.0 ? C6 C7 C8 . . 120.3(2) ? C6 C7 H7 . . 119.8 ? C8 C7 H7 . . 119.8 ? C9 C8 C7 . . 120.23(19) ? C9 C8 H8 . . 119.9 ? C7 C8 H8 . . 119.9 ? C4 C9 C8 . . 118.37(19) ? C4 C9 H9 . . 120.8 ? C8 C9 H9 . . 120.8 ? C11 C10 C15 . . 122.5(2) ? C11 C10 O3 . . 120.66(19) ? C15 C10 O3 . . 116.7(2) ? C10 C11 C12 . . 118.2(2) ? C10 C11 H11 . . 120.9 ? C12 C11 H11 . . 120.9 ? C13 C12 C11 . . 120.3(3) ? C13 C12 H12 . . 119.8 ? C11 C12 H12 . . 119.8 ? C12 C13 C14 . . 120.2(2) ? C12 C13 H13 . . 119.9 ? C14 C13 H13 . . 119.9 ? C15 C14 C13 . . 120.3(3) ? C15 C14 H14 . . 119.8 ? C13 C14 H14 . . 119.8 ? C14 C15 C10 . . 118.4(3) ? C14 C15 H15 . . 120.8 ? C10 C15 H15 . . 120.8 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 P2 N1 P1 . . . . 2.59(18) ? O2 P2 N1 P1 . . . . 127.35(12) ? Cl1 P2 N1 P1 . . . . -121.95(12) ? O1 P1 N1 P2 . . . . -123.97(13) ? N3 P1 N1 P2 . . . . 0.17(17) ? N4 P1 N1 P2 . . . . 129.28(13) ? N1 P2 N2 P3 . . . . -12.29(17) ? O2 P2 N2 P3 . . . . -139.93(11) ? Cl1 P2 N2 P3 . . . . 111.38(11) ? N3 P3 N2 P2 . . . . 19.48(18) ? O3 P3 N2 P2 . . . . 144.54(11) ? Cl2 P3 N2 P2 . . . . -104.88(11) ? O3 P3 N3 P1 . . . . -144.58(12) ? N2 P3 N3 P1 . . . . -17.56(18) ? Cl2 P3 N3 P1 . . . . 105.74(12) ? O1 P1 N3 P3 . . . . 133.43(12) ? N1 P1 N3 P3 . . . . 7.37(17) ? N4 P1 N3 P3 . . . . -120.68(13) ? O1 P1 N4 C3 . . . . 166.03(17) ? N1 P1 N4 C3 . . . . -77.11(19) ? N3 P1 N4 C3 . . . . 52.6(2) ? O1 P1 N4 C2 . . . . 19.68(15) ? N1 P1 N4 C2 . . . . 136.54(14) ? N3 P1 N4 C2 . . . . -93.79(15) ? N1 P1 O1 C1 . . . . -111.60(14) ? N3 P1 O1 C1 . . . . 121.26(14) ? N4 P1 O1 C1 . . . . 4.23(14) ? N1 P2 O2 C4 . . . . 37.43(17) ? N2 P2 O2 C4 . . . . 169.68(14) ? Cl1 P2 O2 C4 . . . . -76.59(14) ? N3 P3 O3 C10 . . . . -167.38(16) ? N2 P3 O3 C10 . . . . 60.91(18) ? Cl2 P3 O3 C10 . . . . -52.81(17) ? P1 O1 C1 C2 . . . . -25.61(19) ? C3 N4 C2 C1 . . . . 177.79(19) ? P1 N4 C2 C1 . . . . -35.27(19) ? O1 C1 C2 N4 . . . . 37.1(2) ? P2 O2 C4 C9 . . . . -89.0(2) ? P2 O2 C4 C5 . . . . 93.3(2) ? C9 C4 C5 C6 . . . . -0.3(3) ? O2 C4 C5 C6 . . . . 177.18(19) ? C4 C5 C6 C7 . . . . 0.1(3) ? C5 C6 C7 C8 . . . . 0.0(4) ? C6 C7 C8 C9 . . . . 0.3(3) ? C5 C4 C9 C8 . . . . 0.6(3) ? O2 C4 C9 C8 . . . . -176.96(18) ? C7 C8 C9 C4 . . . . -0.6(3) ? P3 O3 C10 C11 . . . . -65.3(3) ? P3 O3 C10 C15 . . . . 118.8(2) ? C15 C10 C11 C12 . . . . 0.4(4) ? O3 C10 C11 C12 . . . . -175.2(2) ? C10 C11 C12 C13 . . . . 0.3(4) ? C11 C12 C13 C14 . . . . -0.7(4) ? C12 C13 C14 C15 . . . . 0.4(4) ? C13 C14 C15 C10 . . . . 0.2(4) ? C11 C10 C15 C14 . . . . -0.7(4) ? O3 C10 C15 C14 . . . . 175.1(2) ? #===END data_ETE4a _database_code_depnum_ccdc_archive 'CCDC 865165' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common cyclophosphazene _chemical_formula_moiety ? _chemical_formula_sum 'C11 H23 Cl2 N4 O6 P3' _chemical_formula_iupac ? _chemical_formula_weight 471.14 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_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 16.1437(11) _cell_length_b 7.9041(6) _cell_length_c 16.7683(12) _cell_angle_alpha 90 _cell_angle_beta 108.303(3) _cell_angle_gamma 90 _cell_volume 2031.4(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9366 _cell_measurement_theta_min 2.5588 _cell_measurement_theta_max 28.3215 _cell_measurement_temperature 120.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.080 _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.95 _exptl_special_details ; ; _diffrn_ambient_temperature 120.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 18092 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _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. ; _reflns_number_total 4855 _reflns_number_gt 4287 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.0766 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_number_reflns 4855 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+1.0368P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.384 _refine_diff_density_min -0.315 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.77236(2) 0.23123(5) -0.09053(2) 0.01937(9) Uani d . 1 . . P P2 0.78574(2) 0.54683(5) -0.01488(2) 0.01829(9) Uani d . 1 . . P P3 0.83768(2) 0.26695(5) 0.08373(2) 0.01783(9) Uani d . 1 . . N N1 0.75437(8) 0.42952(16) -0.09460(7) 0.0221(3) Uani d . 1 . . N N2 0.81811(9) 0.46311(16) 0.07534(8) 0.0239(3) Uani d . 1 . . N N3 0.81558(9) 0.15682(16) 0.00196(8) 0.0249(3) Uani d . 1 . . N N4 0.82502(9) 0.17507(18) -0.15612(8) 0.0254(3) Uani d . 1 . . O O1 0.68529(7) 0.13027(16) -0.13587(9) 0.0374(3) Uani d . 1 . . O O2 0.71223(7) 0.67939(13) -0.02068(6) 0.0219(2) Uani d . 1 . . O O3 0.59195(7) 0.70800(13) 0.06943(7) 0.0236(2) Uani d . 1 . . O O4 0.53227(6) 0.49237(14) 0.16834(7) 0.0249(2) Uani d . 1 . . O O5 0.65394(7) 0.18771(13) 0.22071(7) 0.0251(2) Uani d . 1 . . O O6 0.79364(6) 0.18393(12) 0.14497(6) 0.0183(2) Uani d . 1 . . Cl Cl1 0.88526(3) 0.69295(5) -0.02541(3) 0.03341(11) Uani d . 1 . . Cl Cl2 0.96659(3) 0.24066(6) 0.14803(3) 0.03501(11) Uani d . 1 . . C C1 0.69162(13) 0.0347(3) -0.20819(13) 0.0448(5) Uani d . 1 . . H H1A 0.6615 0.0954 -0.261 0.054 Uiso calc R 1 . . H H1B 0.6645 -0.0782 -0.2101 0.054 Uiso calc R 1 . . C C2 0.78768(13) 0.0173(2) -0.19750(11) 0.0365(4) Uani d . 1 . . H H2A 0.8131 -0.0818 -0.1621 0.044 Uiso calc R 1 . . H H2B 0.7976 0.0055 -0.2526 0.044 Uiso calc R 1 . . C C3 0.91969(12) 0.1920(3) -0.12874(13) 0.0418(5) Uani d . 1 . . H H3A 0.9457 0.1065 -0.0859 0.063 Uiso calc R 1 . . H H3B 0.936 0.3051 -0.1051 0.063 Uiso calc R 1 . . H H3C 0.941 0.1758 -0.1769 0.063 Uiso calc R 1 . . C C4 0.72288(10) 0.79830(19) 0.04873(10) 0.0236(3) Uani d . 1 . . H H4A 0.7564 0.8984 0.041 0.028 Uiso calc R 1 . . H H4B 0.7553 0.7436 0.1026 0.028 Uiso calc R 1 . . C C5 0.63406(10) 0.85153(19) 0.05012(10) 0.0246(3) Uani d . 1 . . H H5A 0.6395 0.9406 0.093 0.03 Uiso calc R 1 . . H H5B 0.5998 0.8976 -0.0053 0.03 Uiso calc R 1 . . C C6 0.51425(10) 0.7464(2) 0.08890(11) 0.0269(3) Uani d . 1 . . H H6A 0.4738 0.8117 0.0425 0.032 Uiso calc R 1 . . H H6B 0.5283 0.8153 0.1407 0.032 Uiso calc R 1 . . C C7 0.47259(9) 0.5831(2) 0.10111(10) 0.0267(3) Uani d . 1 . . H H7A 0.4181 0.6062 0.1145 0.032 Uiso calc R 1 . . H H7B 0.4578 0.5151 0.0489 0.032 Uiso calc R 1 . . C C8 0.50827(10) 0.3205(2) 0.17000(11) 0.0284(3) Uani d . 1 . . H H8A 0.5035 0.2665 0.1155 0.034 Uiso calc R 1 . . H H8B 0.4507 0.3128 0.1792 0.034 Uiso calc R 1 . . C C9 0.57616(10) 0.2297(2) 0.23988(11) 0.0277(3) Uani d . 1 . . H H9A 0.5919 0.302 0.2906 0.033 Uiso calc R 1 . . H H9B 0.5502 0.1243 0.2533 0.033 Uiso calc R 1 . . C C10 0.70661(9) 0.33110(18) 0.21789(9) 0.0195(3) Uani d . 1 . . H H10A 0.71 0.4074 0.2656 0.023 Uiso calc R 1 . . H H10B 0.6802 0.3946 0.1651 0.023 Uiso calc R 1 . . C C11 0.79638(9) 0.27283(17) 0.22249(8) 0.0170(3) Uani d . 1 . . H H11A 0.8359 0.3715 0.2305 0.02 Uiso calc R 1 . . H H11B 0.8194 0.1962 0.2711 0.02 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.02100(17) 0.02071(19) 0.01814(18) -0.00229(13) 0.00863(14) -0.00436(14) P2 0.02452(18) 0.01560(18) 0.01495(17) -0.00278(13) 0.00651(13) 0.00160(13) P3 0.02439(18) 0.01526(18) 0.01672(18) -0.00024(13) 0.01058(14) 0.00183(13) N1 0.0280(6) 0.0218(6) 0.0156(6) 0.0015(5) 0.0055(5) -0.0011(5) N2 0.0405(7) 0.0151(6) 0.0155(6) -0.0022(5) 0.0077(5) 0.0000(5) N3 0.0436(7) 0.0154(6) 0.0213(6) 0.0006(5) 0.0181(6) -0.0004(5) N4 0.0299(6) 0.0319(7) 0.0164(6) 0.0072(6) 0.0101(5) -0.0013(5) O1 0.0266(6) 0.0347(7) 0.0500(8) -0.0092(5) 0.0106(5) -0.0194(6) O2 0.0277(5) 0.0179(5) 0.0195(5) -0.0009(4) 0.0063(4) -0.0029(4) O3 0.0233(5) 0.0179(5) 0.0300(6) 0.0020(4) 0.0091(4) -0.0024(4) O4 0.0216(5) 0.0254(6) 0.0243(5) 0.0026(4) 0.0025(4) -0.0032(4) O5 0.0257(5) 0.0190(5) 0.0376(6) -0.0011(4) 0.0198(5) -0.0003(5) O6 0.0252(5) 0.0159(5) 0.0174(5) -0.0017(4) 0.0119(4) -0.0008(4) Cl1 0.0305(2) 0.0326(2) 0.0376(2) -0.01020(16) 0.01140(17) 0.00836(18) Cl2 0.02212(18) 0.0492(3) 0.0366(2) 0.00411(16) 0.01332(16) 0.00370(19) C1 0.0503(11) 0.0372(11) 0.0366(10) -0.0060(9) -0.0009(8) -0.0189(9) C2 0.0570(11) 0.0313(9) 0.0201(8) 0.0127(8) 0.0104(7) -0.0063(7) C3 0.0315(9) 0.0618(13) 0.0394(10) 0.0099(8) 0.0215(8) 0.0085(9) C4 0.0312(8) 0.0171(7) 0.0233(7) -0.0049(6) 0.0095(6) -0.0057(6) C5 0.0323(8) 0.0153(7) 0.0239(7) 0.0022(6) 0.0052(6) -0.0019(6) C6 0.0228(7) 0.0271(8) 0.0287(8) 0.0092(6) 0.0051(6) -0.0022(6) C7 0.0178(6) 0.0333(9) 0.0265(8) 0.0056(6) 0.0036(6) -0.0022(7) C8 0.0233(7) 0.0320(9) 0.0312(8) -0.0033(6) 0.0105(6) -0.0018(7) C9 0.0249(7) 0.0316(9) 0.0325(9) 0.0014(6) 0.0173(6) 0.0035(7) C10 0.0242(7) 0.0157(7) 0.0214(7) 0.0007(5) 0.0112(5) 0.0000(5) C11 0.0225(6) 0.0160(6) 0.0140(6) -0.0005(5) 0.0078(5) -0.0005(5) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.5873(12) ? P1 N1 . 1.5915(13) ? P1 N3 . 1.5994(14) ? P1 N4 . 1.6483(13) ? P2 O2 . 1.5630(11) ? P2 N1 . 1.5742(13) ? P2 N2 . 1.5821(13) ? P2 Cl1 . 2.0309(5) ? P3 O6 . 1.5650(10) ? P3 N3 . 1.5678(13) ? P3 N2 . 1.5798(13) ? P3 Cl2 . 2.0315(6) ? N4 C3 . 1.457(2) ? N4 C2 . 1.462(2) ? O1 C1 . 1.459(2) ? O2 C4 . 1.4635(17) ? O3 C5 . 1.4115(18) ? O3 C6 . 1.4245(18) ? O4 C8 . 1.415(2) ? O4 C7 . 1.4255(18) ? O5 C10 . 1.4265(17) ? O5 C9 . 1.4296(17) ? O6 C11 . 1.4659(16) ? C1 C2 . 1.510(3) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 C5 . 1.501(2) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? C5 H5A . 0.99 ? C5 H5B . 0.99 ? C6 C7 . 1.498(2) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 H7A . 0.99 ? C7 H7B . 0.99 ? C8 C9 . 1.511(2) ? C8 H8A . 0.99 ? C8 H8B . 0.99 ? C9 H9A . 0.99 ? C9 H9B . 0.99 ? C10 C11 . 1.4994(19) ? C10 H10A . 0.99 ? C10 H10B . 0.99 ? C11 H11A . 0.99 ? C11 H11B . 0.99 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N1 . . 110.63(7) ? O1 P1 N3 . . 109.30(7) ? N1 P1 N3 . . 114.95(7) ? O1 P1 N4 . . 96.30(7) ? N1 P1 N4 . . 111.22(7) ? N3 P1 N4 . . 112.87(7) ? O2 P2 N1 . . 107.85(6) ? O2 P2 N2 . . 110.87(6) ? N1 P2 N2 . . 119.16(7) ? O2 P2 Cl1 . . 102.67(4) ? N1 P2 Cl1 . . 108.27(5) ? N2 P2 Cl1 . . 106.75(5) ? O6 P3 N3 . . 108.40(6) ? O6 P3 N2 . . 110.52(6) ? N3 P3 N2 . . 118.87(7) ? O6 P3 Cl2 . . 102.10(4) ? N3 P3 Cl2 . . 108.74(6) ? N2 P3 Cl2 . . 106.89(5) ? P2 N1 P1 . . 122.54(8) ? P3 N2 P2 . . 119.50(8) ? P3 N3 P1 . . 123.65(8) ? C3 N4 C2 . . 117.59(15) ? C3 N4 P1 . . 118.34(11) ? C2 N4 P1 . . 108.92(11) ? C1 O1 P1 . . 112.07(11) ? C4 O2 P2 . . 118.93(9) ? C5 O3 C6 . . 113.81(11) ? C8 O4 C7 . . 112.17(12) ? C10 O5 C9 . . 113.44(11) ? C11 O6 P3 . . 119.17(8) ? O1 C1 C2 . . 106.60(14) ? O1 C1 H1A . . 110.4 ? C2 C1 H1A . . 110.4 ? O1 C1 H1B . . 110.4 ? C2 C1 H1B . . 110.4 ? H1A C1 H1B . . 108.6 ? N4 C2 C1 . . 103.52(13) ? N4 C2 H2A . . 111.1 ? C1 C2 H2A . . 111.1 ? N4 C2 H2B . . 111.1 ? C1 C2 H2B . . 111.1 ? H2A C2 H2B . . 109.0 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O2 C4 C5 . . 108.55(12) ? O2 C4 H4A . . 110.0 ? C5 C4 H4A . . 110.0 ? O2 C4 H4B . . 110.0 ? C5 C4 H4B . . 110.0 ? H4A C4 H4B . . 108.4 ? O3 C5 C4 . . 108.02(12) ? O3 C5 H5A . . 110.1 ? C4 C5 H5A . . 110.1 ? O3 C5 H5B . . 110.1 ? C4 C5 H5B . . 110.1 ? H5A C5 H5B . . 108.4 ? O3 C6 C7 . . 108.26(12) ? O3 C6 H6A . . 110.0 ? C7 C6 H6A . . 110.0 ? O3 C6 H6B . . 110.0 ? C7 C6 H6B . . 110.0 ? H6A C6 H6B . . 108.4 ? O4 C7 C6 . . 108.69(12) ? O4 C7 H7A . . 110.0 ? C6 C7 H7A . . 110.0 ? O4 C7 H7B . . 110.0 ? C6 C7 H7B . . 110.0 ? H7A C7 H7B . . 108.3 ? O4 C8 C9 . . 109.55(13) ? O4 C8 H8A . . 109.8 ? C9 C8 H8A . . 109.8 ? O4 C8 H8B . . 109.8 ? C9 C8 H8B . . 109.8 ? H8A C8 H8B . . 108.2 ? O5 C9 C8 . . 114.23(13) ? O5 C9 H9A . . 108.7 ? C8 C9 H9A . . 108.7 ? O5 C9 H9B . . 108.7 ? C8 C9 H9B . . 108.7 ? H9A C9 H9B . . 107.6 ? O5 C10 C11 . . 109.31(11) ? O5 C10 H10A . . 109.8 ? C11 C10 H10A . . 109.8 ? O5 C10 H10B . . 109.8 ? C11 C10 H10B . . 109.8 ? H10A C10 H10B . . 108.3 ? O6 C11 C10 . . 110.01(11) ? O6 C11 H11A . . 109.7 ? C10 C11 H11A . . 109.7 ? O6 C11 H11B . . 109.7 ? C10 C11 H11B . . 109.7 ? H11A C11 H11B . . 108.2 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 P2 N1 P1 . . . . -140.90(8) ? N2 P2 N1 P1 . . . . -13.44(13) ? Cl1 P2 N1 P1 . . . . 108.68(8) ? O1 P1 N1 P2 . . . . 130.63(9) ? N3 P1 N1 P2 . . . . 6.24(12) ? N4 P1 N1 P2 . . . . -123.59(9) ? O6 P3 N2 P2 . . . . -132.29(8) ? N3 P3 N2 P2 . . . . -6.05(13) ? Cl2 P3 N2 P2 . . . . 117.37(8) ? O2 P2 N2 P3 . . . . 139.11(8) ? N1 P2 N2 P3 . . . . 13.07(13) ? Cl1 P2 N2 P3 . . . . -109.81(8) ? O6 P3 N3 P1 . . . . 126.14(9) ? N2 P3 N3 P1 . . . . -1.11(13) ? Cl2 P3 N3 P1 . . . . -123.61(9) ? O1 P1 N3 P3 . . . . -123.97(10) ? N1 P1 N3 P3 . . . . 1.11(13) ? N4 P1 N3 P3 . . . . 130.13(10) ? O1 P1 N4 C3 . . . . -161.23(14) ? N1 P1 N4 C3 . . . . 83.74(14) ? N3 P1 N4 C3 . . . . -47.18(15) ? O1 P1 N4 C2 . . . . -23.40(12) ? N1 P1 N4 C2 . . . . -138.44(11) ? N3 P1 N4 C2 . . . . 90.64(12) ? N1 P1 O1 C1 . . . . 117.56(13) ? N3 P1 O1 C1 . . . . -114.89(13) ? N4 P1 O1 C1 . . . . 2.05(14) ? N1 P2 O2 C4 . . . . 176.42(10) ? N2 P2 O2 C4 . . . . 44.31(12) ? Cl1 P2 O2 C4 . . . . -69.38(10) ? N3 P3 O6 C11 . . . . -173.36(10) ? N2 P3 O6 C11 . . . . -41.46(11) ? Cl2 P3 O6 C11 . . . . 71.97(9) ? P1 O1 C1 C2 . . . . 18.9(2) ? C3 N4 C2 C1 . . . . 173.92(15) ? P1 N4 C2 C1 . . . . 35.74(16) ? O1 C1 C2 N4 . . . . -33.53(19) ? P2 O2 C4 C5 . . . . -153.58(10) ? C6 O3 C5 C4 . . . . 168.40(12) ? O2 C4 C5 O3 . . . . 65.29(15) ? C5 O3 C6 C7 . . . . 175.44(12) ? C8 O4 C7 C6 . . . . -164.56(12) ? O3 C6 C7 O4 . . . . 59.87(16) ? C7 O4 C8 C9 . . . . 177.34(12) ? C10 O5 C9 C8 . . . . 71.06(17) ? O4 C8 C9 O5 . . . . -77.63(17) ? C9 O5 C10 C11 . . . . 163.74(12) ? P3 O6 C11 C10 . . . . 111.57(11) ? O5 C10 C11 O6 . . . . 69.06(14) ? #===END data_ETE5a _database_code_depnum_ccdc_archive 'CCDC 865166' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Cl2 N4 O3 P3' _chemical_formula_iupac ? _chemical_formula_weight 353.01 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_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 15.4585(4) _cell_length_b 7.9301(2) _cell_length_c 22.5964(6) _cell_angle_alpha 90 _cell_angle_beta 97.0900(10) _cell_angle_gamma 90 _cell_volume 2748.85(12) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9891 _cell_measurement_theta_min 2.6555 _cell_measurement_theta_max 28.2758 _cell_measurement_temperature 120.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.670 _exptl_crystal_size_mid 0.570 _exptl_crystal_size_min 0.380 _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.74 _exptl_special_details ; ; _diffrn_ambient_temperature 120.(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 21731 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _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. ; _reflns_number_total 4859 _reflns_number_gt 4519 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.0691 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_number_reflns 4859 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.6032P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.389 _refine_diff_density_min -0.341 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.64147(3) 0.79855(5) 0.575722(18) 0.01310(11) Uani d . 1 . . P P2 0.52180(3) 0.76451(5) 0.656271(18) 0.01259(10) Uani d . 1 . . P P3 0.63381(3) 0.51975(5) 0.647193(18) 0.01266(10) Uani d . 1 . . P P4 0.64605(3) 0.81084(5) 0.084897(18) 0.01277(10) Uani d . 1 . . P P5 0.62311(3) 0.52464(5) 0.153519(18) 0.01241(10) Uani d . 1 . . P P6 0.51712(3) 0.78650(5) 0.157538(18) 0.01223(10) Uani d . 1 . . N N1 0.55816(9) 0.86512(18) 0.60435(6) 0.0163(3) Uani d . 1 . . N N2 0.53731(9) 0.56562(17) 0.65933(6) 0.0143(3) Uani d . 1 . . N N3 0.67112(9) 0.61045(17) 0.59355(6) 0.0161(3) Uani d . 1 . . N N4 0.63300(9) 0.82355(19) 0.50313(6) 0.0193(3) Uani d . 1 . . N N5 0.67490(9) 0.62806(18) 0.10963(6) 0.0165(3) Uani d . 1 . . N N6 0.52631(9) 0.58676(17) 0.15926(6) 0.0144(3) Uani d . 1 . . N N7 0.55969(9) 0.88481(17) 0.10775(6) 0.0151(3) Uani d . 1 . . N N8 0.64288(9) 0.82195(19) 0.01188(6) 0.0200(3) Uani d . 1 . . O O1 0.71955(8) 0.92834(16) 0.59130(5) 0.0207(3) Uani d . 1 . . O O2 0.55841(7) 0.84890(14) 0.71748(5) 0.0170(3) Uani d . 1 . . O O3 0.70067(7) 0.54951(15) 0.70481(5) 0.0171(3) Uani d . 1 . . O O4 0.72373(8) 0.94078(16) 0.10027(5) 0.0207(3) Uani d . 1 . . O O5 0.67735(7) 0.50338(14) 0.21718(5) 0.0172(3) Uani d . 1 . . O O6 0.55285(7) 0.86468(14) 0.22037(5) 0.0161(2) Uani d . 1 . . Cl Cl1 0.39277(3) 0.79991(6) 0.650245(19) 0.02165(11) Uani d . 1 . . Cl Cl2 0.63553(3) 0.27085(5) 0.633459(19) 0.02131(11) Uani d . 1 . . Cl Cl3 0.61690(3) 0.28328(5) 0.129101(18) 0.01916(11) Uani d . 1 . . Cl Cl4 0.38948(3) 0.83686(6) 0.147634(18) 0.02023(11) Uani d . 1 . . C C1 0.75178(13) 0.9942(3) 0.53826(9) 0.0313(5) Uani d . 1 . . H H1A 0.8029 0.9286 0.529 0.038 Uiso calc R 1 . . H H1B 0.7692 1.1138 0.5441 0.038 Uiso calc R 1 . . C C2 0.67700(13) 0.9778(3) 0.48819(8) 0.0293(4) Uani d . 1 . . H H2A 0.6374 1.076 0.4873 0.035 Uiso calc R 1 . . H H2B 0.699 0.9676 0.449 0.035 Uiso calc R 1 . . C C3 0.55477(13) 0.7721(3) 0.46467(8) 0.0283(4) Uani d . 1 . . H H3A 0.5133 0.866 0.4602 0.042 Uiso calc R 1 . . H H3B 0.5281 0.6755 0.4825 0.042 Uiso calc R 1 . . H H3C 0.5703 0.7403 0.4254 0.042 Uiso calc R 1 . . C C4 0.55795(12) 0.7524(2) 0.77281(7) 0.0197(4) Uani d . 1 . . H H4A 0.515 0.6596 0.7661 0.024 Uiso calc R 1 . . H H4B 0.5398 0.8269 0.8042 0.024 Uiso calc R 1 . . C C5 0.64748(12) 0.6795(2) 0.79369(7) 0.0224(4) Uani d . 1 . . H H5A 0.6912 0.7677 0.7884 0.027 Uiso calc R 1 . . H H5B 0.6504 0.6576 0.837 0.027 Uiso calc R 1 . . C C6 0.67543(11) 0.5196(2) 0.76447(7) 0.0206(4) Uani d . 1 . . H H6A 0.7253 0.4692 0.7901 0.025 Uiso calc R 1 . . H H6B 0.6268 0.4375 0.7614 0.025 Uiso calc R 1 . . C C7 0.75757(13) 1.0024(3) 0.04715(9) 0.0349(5) Uani d . 1 . . H H7A 0.8101 0.938 0.0398 0.042 Uiso calc R 1 . . H H7B 0.7733 1.1232 0.0516 0.042 Uiso calc R 1 . . C C8 0.68514(13) 0.9778(3) -0.00379(9) 0.0329(5) Uani d . 1 . . H H8A 0.6438 1.0736 -0.0065 0.039 Uiso calc R 1 . . H H8B 0.709 0.9661 -0.0423 0.039 Uiso calc R 1 . . C C9 0.56480(12) 0.7693(3) -0.02657(8) 0.0290(4) Uani d . 1 . . H H9A 0.5226 0.862 -0.0306 0.044 Uiso calc R 1 . . H H9B 0.539 0.6713 -0.0089 0.044 Uiso calc R 1 . . H H9C 0.5804 0.7391 -0.066 0.044 Uiso calc R 1 . . C C10 0.70942(11) 0.6563(2) 0.24958(7) 0.0198(4) Uani d . 1 . . H H10A 0.7133 0.7485 0.2205 0.024 Uiso calc R 1 . . H H10B 0.7689 0.6346 0.2697 0.024 Uiso calc R 1 . . C C11 0.65224(11) 0.7137(2) 0.29573(7) 0.0202(4) Uani d . 1 . . H H11A 0.6803 0.8131 0.3165 0.024 Uiso calc R 1 . . H H11B 0.6517 0.6228 0.3257 0.024 Uiso calc R 1 . . C C12 0.55828(11) 0.7597(2) 0.27401(7) 0.0181(4) Uani d . 1 . . H H12A 0.5239 0.6555 0.2652 0.022 Uiso calc R 1 . . H H12B 0.5329 0.8215 0.3058 0.022 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0141(2) 0.0140(2) 0.0116(2) 0.00097(16) 0.00325(16) 0.00132(15) P2 0.0118(2) 0.0128(2) 0.0136(2) 0.00126(16) 0.00312(16) 0.00072(16) P3 0.0123(2) 0.0108(2) 0.0148(2) 0.00101(16) 0.00139(16) 0.00075(16) P4 0.0128(2) 0.0128(2) 0.0131(2) 0.00017(16) 0.00316(16) 0.00117(15) P5 0.0130(2) 0.0096(2) 0.0143(2) 0.00094(16) 0.00008(16) 0.00014(15) P6 0.0115(2) 0.0120(2) 0.0134(2) 0.00160(16) 0.00266(16) 0.00157(15) N1 0.0186(7) 0.0137(7) 0.0175(7) 0.0045(6) 0.0064(6) 0.0040(6) N2 0.0131(7) 0.0138(7) 0.0161(6) -0.0005(6) 0.0024(5) 0.0008(5) N3 0.0159(7) 0.0159(7) 0.0175(7) 0.0041(6) 0.0061(5) 0.0014(6) N4 0.0207(8) 0.0239(8) 0.0135(7) 0.0024(6) 0.0035(6) 0.0038(6) N5 0.0142(7) 0.0153(7) 0.0207(7) 0.0031(6) 0.0053(6) 0.0019(6) N6 0.0141(7) 0.0125(7) 0.0167(7) -0.0015(6) 0.0022(5) 0.0017(5) N7 0.0169(7) 0.0116(7) 0.0175(7) 0.0028(6) 0.0048(5) 0.0037(5) N8 0.0194(8) 0.0284(9) 0.0128(7) 0.0037(6) 0.0043(6) 0.0035(6) O1 0.0189(6) 0.0206(7) 0.0228(6) -0.0046(5) 0.0036(5) 0.0022(5) O2 0.0212(6) 0.0150(6) 0.0150(6) -0.0023(5) 0.0027(5) 0.0004(5) O3 0.0144(6) 0.0209(6) 0.0157(6) -0.0008(5) 0.0010(4) 0.0014(5) O4 0.0166(6) 0.0195(7) 0.0257(6) -0.0046(5) 0.0013(5) 0.0034(5) O5 0.0192(6) 0.0138(6) 0.0172(6) 0.0024(5) -0.0029(5) -0.0014(5) O6 0.0202(6) 0.0134(6) 0.0148(5) 0.0001(5) 0.0025(5) 0.0004(5) Cl1 0.0125(2) 0.0267(2) 0.0262(2) 0.00438(17) 0.00432(17) 0.00100(17) Cl2 0.0218(2) 0.0115(2) 0.0299(2) 0.00230(16) 0.00054(17) -0.00152(16) Cl3 0.0225(2) 0.0108(2) 0.0234(2) 0.00129(16) -0.00026(17) -0.00317(15) Cl4 0.0121(2) 0.0226(2) 0.0263(2) 0.00437(16) 0.00331(16) 0.00479(17) C1 0.0250(10) 0.0328(12) 0.0381(11) -0.0063(9) 0.0121(9) 0.0107(9) C2 0.0326(11) 0.0307(11) 0.0268(10) 0.0041(9) 0.0124(8) 0.0137(8) C3 0.0274(10) 0.0364(12) 0.0192(9) 0.0086(9) -0.0044(8) -0.0029(8) C4 0.0257(10) 0.0209(9) 0.0133(8) -0.0007(7) 0.0058(7) 0.0004(7) C5 0.0241(10) 0.0288(10) 0.0136(8) -0.0016(8) -0.0005(7) 0.0005(7) C6 0.0219(9) 0.0250(10) 0.0141(8) 0.0000(8) -0.0005(7) 0.0060(7) C7 0.0217(10) 0.0393(12) 0.0447(12) -0.0068(9) 0.0080(9) 0.0223(10) C8 0.0257(11) 0.0426(13) 0.0322(11) 0.0027(9) 0.0109(8) 0.0217(9) C9 0.0255(10) 0.0410(12) 0.0189(9) 0.0093(9) -0.0040(8) -0.0066(8) C10 0.0160(8) 0.0213(9) 0.0206(8) -0.0016(7) -0.0033(7) -0.0058(7) C11 0.0217(9) 0.0222(10) 0.0157(8) 0.0006(7) -0.0013(7) -0.0025(7) C12 0.0212(9) 0.0198(9) 0.0137(8) 0.0000(7) 0.0042(7) 0.0020(7) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . 1.5923(13) ? P1 N3 . 1.5975(14) ? P1 N1 . 1.6004(14) ? P1 N4 . 1.6414(14) ? P2 O2 . 1.5773(11) ? P2 N1 . 1.5786(14) ? P2 N2 . 1.5956(14) ? P2 Cl1 . 2.0022(6) ? P3 O3 . 1.5769(11) ? P3 N3 . 1.5785(14) ? P3 N2 . 1.5919(14) ? P3 Cl2 . 1.9987(6) ? P4 O4 . 1.5879(12) ? P4 N5 . 1.5971(14) ? P4 N7 . 1.6010(14) ? P4 N8 . 1.6469(14) ? P5 N5 . 1.5790(14) ? P5 O5 . 1.5821(11) ? P5 N6 . 1.5957(14) ? P5 Cl3 . 1.9910(6) ? P6 N7 . 1.5778(14) ? P6 O6 . 1.5848(11) ? P6 N6 . 1.5903(14) ? P6 Cl4 . 1.9984(6) ? N4 C3 . 1.458(2) ? N4 C2 . 1.459(2) ? N8 C9 . 1.459(2) ? N8 C8 . 1.462(2) ? O1 C1 . 1.451(2) ? O2 C4 . 1.467(2) ? O3 C6 . 1.4683(19) ? O4 C7 . 1.452(2) ? O5 C10 . 1.470(2) ? O6 C12 . 1.4642(19) ? C1 C2 . 1.520(3) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 C5 . 1.520(2) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? C5 C6 . 1.517(2) ? C5 H5A . 0.99 ? C5 H5B . 0.99 ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C8 . 1.516(3) ? C7 H7A . 0.99 ? C7 H7B . 0.99 ? C8 H8A . 0.99 ? C8 H8B . 0.99 ? C9 H9A . 0.98 ? C9 H9B . 0.98 ? C9 H9C . 0.98 ? C10 C11 . 1.518(2) ? C10 H10A . 0.99 ? C10 H10B . 0.99 ? C11 C12 . 1.519(2) ? C11 H11A . 0.99 ? C11 H11B . 0.99 ? C12 H12A . 0.99 ? C12 H12B . 0.99 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 P1 N3 . . 111.21(7) ? O1 P1 N1 . . 108.86(7) ? N3 P1 N1 . . 115.23(7) ? O1 P1 N4 . . 96.18(7) ? N3 P1 N4 . . 110.48(7) ? N1 P1 N4 . . 113.28(7) ? O2 P2 N1 . . 108.37(7) ? O2 P2 N2 . . 110.22(7) ? N1 P2 N2 . . 117.80(7) ? O2 P2 Cl1 . . 104.29(5) ? N1 P2 Cl1 . . 108.77(6) ? N2 P2 Cl1 . . 106.54(5) ? O3 P3 N3 . . 107.54(7) ? O3 P3 N2 . . 110.87(7) ? N3 P3 N2 . . 117.85(7) ? O3 P3 Cl2 . . 104.84(5) ? N3 P3 Cl2 . . 108.52(6) ? N2 P3 Cl2 . . 106.45(6) ? O4 P4 N5 . . 109.97(7) ? O4 P4 N7 . . 109.26(7) ? N5 P4 N7 . . 115.31(7) ? O4 P4 N8 . . 96.47(7) ? N5 P4 N8 . . 111.82(8) ? N7 P4 N8 . . 112.37(7) ? N5 P5 O5 . . 111.93(7) ? N5 P5 N6 . . 116.36(7) ? O5 P5 N6 . . 110.86(7) ? N5 P5 Cl3 . . 109.64(6) ? O5 P5 Cl3 . . 98.71(5) ? N6 P5 Cl3 . . 107.80(5) ? N7 P6 O6 . . 108.40(7) ? N7 P6 N6 . . 117.76(7) ? O6 P6 N6 . . 110.34(7) ? N7 P6 Cl4 . . 108.32(5) ? O6 P6 Cl4 . . 104.61(5) ? N6 P6 Cl4 . . 106.61(5) ? P2 N1 P1 . . 120.78(9) ? P3 N2 P2 . . 110.94(8) ? P3 N3 P1 . . 119.90(8) ? C3 N4 C2 . . 118.22(15) ? C3 N4 P1 . . 121.33(12) ? C2 N4 P1 . . 110.52(12) ? P5 N5 P4 . . 123.36(9) ? P6 N6 P5 . . 112.79(8) ? P6 N7 P4 . . 119.13(8) ? C9 N8 C8 . . 117.36(15) ? C9 N8 P4 . . 120.11(12) ? C8 N8 P4 . . 109.21(12) ? C1 O1 P1 . . 112.23(11) ? C4 O2 P2 . . 119.16(10) ? C6 O3 P3 . . 120.83(10) ? C7 O4 P4 . . 112.19(12) ? C10 O5 P5 . . 118.24(10) ? C12 O6 P6 . . 119.83(10) ? O1 C1 C2 . . 106.07(14) ? O1 C1 H1A . . 110.5 ? C2 C1 H1A . . 110.5 ? O1 C1 H1B . . 110.5 ? C2 C1 H1B . . 110.5 ? H1A C1 H1B . . 108.7 ? N4 C2 C1 . . 103.48(15) ? N4 C2 H2A . . 111.1 ? C1 C2 H2A . . 111.1 ? N4 C2 H2B . . 111.1 ? C1 C2 H2B . . 111.1 ? H2A C2 H2B . . 109.0 ? N4 C3 H3A . . 109.5 ? N4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? N4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? O2 C4 C5 . . 111.28(14) ? O2 C4 H4A . . 109.4 ? C5 C4 H4A . . 109.4 ? O2 C4 H4B . . 109.4 ? C5 C4 H4B . . 109.4 ? H4A C4 H4B . . 108.0 ? C6 C5 C4 . . 118.70(15) ? C6 C5 H5A . . 107.6 ? C4 C5 H5A . . 107.6 ? C6 C5 H5B . . 107.6 ? C4 C5 H5B . . 107.6 ? H5A C5 H5B . . 107.1 ? O3 C6 C5 . . 112.76(14) ? O3 C6 H6A . . 109.0 ? C5 C6 H6A . . 109.0 ? O3 C6 H6B . . 109.0 ? C5 C6 H6B . . 109.0 ? H6A C6 H6B . . 107.8 ? O4 C7 C8 . . 106.06(14) ? O4 C7 H7A . . 110.5 ? C8 C7 H7A . . 110.5 ? O4 C7 H7B . . 110.5 ? C8 C7 H7B . . 110.5 ? H7A C7 H7B . . 108.7 ? N8 C8 C7 . . 103.60(15) ? N8 C8 H8A . . 111.0 ? C7 C8 H8A . . 111.0 ? N8 C8 H8B . . 111.0 ? C7 C8 H8B . . 111.0 ? H8A C8 H8B . . 109.0 ? N8 C9 H9A . . 109.5 ? N8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? N8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? O5 C10 C11 . . 113.61(14) ? O5 C10 H10A . . 108.8 ? C11 C10 H10A . . 108.8 ? O5 C10 H10B . . 108.8 ? C11 C10 H10B . . 108.8 ? H10A C10 H10B . . 107.7 ? C10 C11 C12 . . 117.71(14) ? C10 C11 H11A . . 107.9 ? C12 C11 H11A . . 107.9 ? C10 C11 H11B . . 107.9 ? C12 C11 H11B . . 107.9 ? H11A C11 H11B . . 107.2 ? O6 C12 C11 . . 111.02(14) ? O6 C12 H12A . . 109.4 ? C11 C12 H12A . . 109.4 ? O6 C12 H12B . . 109.4 ? C11 C12 H12B . . 109.4 ? H12A C12 H12B . . 108.0 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 P2 N1 P1 . . . . 98.00(10) ? N2 P2 N1 P1 . . . . -27.94(13) ? Cl1 P2 N1 P1 . . . . -149.20(8) ? O1 P1 N1 P2 . . . . -113.69(10) ? N3 P1 N1 P2 . . . . 12.01(13) ? N4 P1 N1 P2 . . . . 140.60(10) ? O3 P3 N2 P2 . . . . 79.44(9) ? N3 P3 N2 P2 . . . . -45.04(11) ? Cl2 P3 N2 P2 . . . . -167.08(6) ? O2 P2 N2 P3 . . . . -82.26(9) ? N1 P2 N2 P3 . . . . 42.77(11) ? Cl1 P2 N2 P3 . . . . 165.17(6) ? O3 P3 N3 P1 . . . . -93.93(10) ? N2 P3 N3 P1 . . . . 32.19(13) ? Cl2 P3 N3 P1 . . . . 153.17(7) ? O1 P1 N3 P3 . . . . 110.52(10) ? N1 P1 N3 P3 . . . . -13.96(13) ? N4 P1 N3 P3 . . . . -143.92(9) ? O1 P1 N4 C3 . . . . -161.91(14) ? N3 P1 N4 C3 . . . . 82.69(15) ? N1 P1 N4 C3 . . . . -48.30(16) ? O1 P1 N4 C2 . . . . -16.95(13) ? N3 P1 N4 C2 . . . . -132.35(12) ? N1 P1 N4 C2 . . . . 96.66(13) ? O5 P5 N5 P4 . . . . -113.05(10) ? N6 P5 N5 P4 . . . . 15.85(13) ? Cl3 P5 N5 P4 . . . . 138.47(8) ? O4 P4 N5 P5 . . . . 124.12(10) ? N7 P4 N5 P5 . . . . 0.05(13) ? N8 P4 N5 P5 . . . . -129.95(10) ? N7 P6 N6 P5 . . . . 46.31(11) ? O6 P6 N6 P5 . . . . -78.82(9) ? Cl4 P6 N6 P5 . . . . 168.15(6) ? N5 P5 N6 P6 . . . . -37.67(11) ? O5 P5 N6 P6 . . . . 91.74(9) ? Cl3 P5 N6 P6 . . . . -161.24(6) ? O6 P6 N7 P4 . . . . 94.59(10) ? N6 P6 N7 P4 . . . . -31.48(13) ? Cl4 P6 N7 P4 . . . . -152.44(7) ? O4 P4 N7 P6 . . . . -117.04(9) ? N5 P4 N7 P6 . . . . 7.40(13) ? N8 P4 N7 P6 . . . . 137.13(9) ? O4 P4 N8 C9 . . . . -159.96(14) ? N5 P4 N8 C9 . . . . 85.49(15) ? N7 P4 N8 C9 . . . . -46.03(16) ? O4 P4 N8 C8 . . . . -20.09(13) ? N5 P4 N8 C8 . . . . -134.65(12) ? N7 P4 N8 C8 . . . . 93.84(13) ? N3 P1 O1 C1 . . . . 109.68(13) ? N1 P1 O1 C1 . . . . -122.31(13) ? N4 P1 O1 C1 . . . . -5.12(13) ? N1 P2 O2 C4 . . . . -160.96(12) ? N2 P2 O2 C4 . . . . -30.71(13) ? Cl1 P2 O2 C4 . . . . 83.30(11) ? N3 P3 O3 C6 . . . . 164.21(12) ? N2 P3 O3 C6 . . . . 34.06(14) ? Cl2 P3 O3 C6 . . . . -80.43(12) ? N5 P4 O4 C7 . . . . 113.89(13) ? N7 P4 O4 C7 . . . . -118.60(13) ? N8 P4 O4 C7 . . . . -2.16(13) ? N5 P5 O5 C10 . . . . 55.91(13) ? N6 P5 O5 C10 . . . . -75.82(12) ? Cl3 P5 O5 C10 . . . . 171.26(10) ? N7 P6 O6 C12 . . . . -152.16(11) ? N6 P6 O6 C12 . . . . -21.87(13) ? Cl4 P6 O6 C12 . . . . 92.44(11) ? P1 O1 C1 C2 . . . . 24.27(19) ? C3 N4 C2 C1 . . . . 177.91(15) ? P1 N4 C2 C1 . . . . 31.73(17) ? O1 C1 C2 N4 . . . . -34.0(2) ? P2 O2 C4 C5 . . . . 100.50(15) ? O2 C4 C5 C6 . . . . -80.07(19) ? P3 O3 C6 C5 . . . . -96.76(15) ? C4 C5 C6 O3 . . . . 75.9(2) ? P4 O4 C7 C8 . . . . 22.6(2) ? C9 N8 C8 C7 . . . . 175.32(16) ? P4 N8 C8 C7 . . . . 34.22(18) ? O4 C7 C8 N8 . . . . -34.8(2) ? P5 O5 C10 C11 . . . . 98.19(15) ? O5 C10 C11 C12 . . . . -60.5(2) ? P6 O6 C12 C11 . . . . 106.53(14) ? C10 C11 C12 O6 . . . . -44.8(2) ? #===END