Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Serap Besli' _publ_contact_author_address ; Science Faculty, Chemistry Gebze Institute of Technology Istanbul Cad. No: 101 P.B. 141 Gebze Kocaeli 41400 TURKEY ; _publ_contact_author_email BESLI@GYTE.EDU.TR _publ_section_title ; A spiro to ansa rearrangement in cyclotriphosphazene derivatives ; _database_code_CSD ? loop_ _publ_author_name 'Serap Besli' 'Simon Coles ' 'David B. Davis ' 'M. Hursthouse ' 'Adem Kilic ' 'Robert A. Shaw ' data_5a _database_code_depnum_ccdc_archive 'CCDC 242926' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H21 Cl2 N4 O6 P3' _chemical_formula_weight 457.12 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.94690(10) _cell_length_b 14.13320(10) _cell_length_c 15.05620(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.9716(4) _cell_angle_gamma 90.00 _cell_volume 1885.44(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 45011 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8945 _exptl_absorpt_correction_T_max 0.9393 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 39331 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4312 _reflns_number_gt 3916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+1.4333P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4312 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8093(3) 0.62799(17) 0.30603(17) 0.0492(6) Uani 1 1 d . . . H1A H 0.8024 0.6950 0.3187 0.059 Uiso 1 1 calc R . . H1B H 0.7417 0.6151 0.2513 0.059 Uiso 1 1 calc R . . C2 C 0.9697(3) 0.60620(16) 0.28984(18) 0.0471(5) Uani 1 1 d . . . H2A H 1.0087 0.6609 0.2617 0.057 Uiso 1 1 calc R . . H2B H 1.0312 0.5974 0.3475 0.057 Uiso 1 1 calc R . . C3 C 0.6123(3) 0.19423(17) 0.18716(19) 0.0527(6) Uani 1 1 d . . . H3A H 0.7115 0.1944 0.1681 0.063 Uiso 1 1 calc R . . H3B H 0.5458 0.1567 0.1446 0.063 Uiso 1 1 calc R . . C4 C 0.6223(3) 0.1507(2) 0.2773(2) 0.0677(8) Uani 1 1 d . . . H4A H 0.5305 0.1631 0.3029 0.081 Uiso 1 1 calc R . . H4B H 0.6343 0.0827 0.2729 0.081 Uiso 1 1 calc R . . C5 C 0.7553(4) 0.1601(3) 0.4234(2) 0.0815(11) Uani 1 1 d . . . H5A H 0.7360 0.0927 0.4261 0.098 Uiso 1 1 calc R . . H5B H 0.6796 0.1931 0.4519 0.098 Uiso 1 1 calc R . . C6 C 0.9055(4) 0.1814(3) 0.4703(2) 0.0746(9) Uani 1 1 d . . . H6A H 0.9319 0.2463 0.4584 0.090 Uiso 1 1 calc R . . H6B H 0.9059 0.1745 0.5344 0.090 Uiso 1 1 calc R . . C7 C 1.1592(5) 0.1262(3) 0.4908(2) 0.0898(12) Uani 1 1 d . . . H7A H 1.2193 0.0738 0.4739 0.108 Uiso 1 1 calc R . . H7B H 1.1498 0.1185 0.5538 0.108 Uiso 1 1 calc R . . C8 C 1.2403(5) 0.2117(3) 0.4809(2) 0.0918(12) Uani 1 1 d . A . H8A H 1.1904 0.2633 0.5075 0.110 Uiso 1 1 calc R . . H8B H 1.3411 0.2057 0.5137 0.110 Uiso 1 1 calc R . . C9 C 1.2686(4) 0.3390(3) 0.3893(3) 0.0612(13) Uani 0.804(9) 1 d P A 1 H9A H 1.1984 0.3678 0.4249 0.073 Uiso 0.804(9) 1 calc PR A 1 H9B H 1.3701 0.3561 0.4157 0.073 Uiso 0.804(9) 1 calc PR A 1 C9' C 1.3303(12) 0.2978(8) 0.3569(8) 0.038(3) Uani 0.196(9) 1 d P A 2 H9'1 H 1.3948 0.2664 0.3193 0.046 Uiso 0.196(9) 1 calc PR A 2 H9'2 H 1.3954 0.3283 0.4055 0.046 Uiso 0.196(9) 1 calc PR A 2 C10 C 1.2410(3) 0.3732(2) 0.3020(3) 0.0860(13) Uani 1 1 d . . . H10A H 1.3163 0.3474 0.2682 0.103 Uiso 1 1 calc R A 1 H10B H 1.2530 0.4415 0.3034 0.103 Uiso 1 1 calc R A 1 N1 N 0.61946(19) 0.43120(15) 0.29571(12) 0.0407(4) Uani 1 1 d . . . N2 N 0.82385(19) 0.36426(14) 0.19271(12) 0.0391(4) Uani 1 1 d . A . N3 N 0.91504(19) 0.42172(12) 0.36338(11) 0.0347(4) Uani 1 1 d . A . N4 N 0.9884(2) 0.52302(14) 0.23418(14) 0.0439(4) Uani 1 1 d D A . O1 O 0.75654(19) 0.57454(11) 0.37977(11) 0.0447(4) Uani 1 1 d . . . O2 O 0.55641(17) 0.28949(12) 0.18707(13) 0.0479(4) Uani 1 1 d . . . O3 O 0.7467(2) 0.18935(15) 0.33228(14) 0.0628(5) Uani 1 1 d . . . O4 O 1.0129(2) 0.11890(14) 0.44098(12) 0.0589(5) Uani 1 1 d . . . O5 O 1.2516(2) 0.23466(16) 0.39062(14) 0.0672(5) Uani 1 1 d . . . O6 O 1.09342(16) 0.35090(12) 0.25559(13) 0.0475(4) Uani 1 1 d . A . P1 P 0.75338(6) 0.46292(4) 0.37018(3) 0.03317(15) Uani 1 1 d . A . P2 P 0.65515(5) 0.38045(4) 0.20719(3) 0.03229(15) Uani 1 1 d . . . P3 P 0.95160(5) 0.41469(4) 0.26241(3) 0.03253(15) Uani 1 1 d . . . Cl1 Cl 0.69621(8) 0.43024(5) 0.49024(4) 0.05421(19) Uani 1 1 d . . . Cl2 Cl 0.54946(8) 0.46034(5) 0.10485(4) 0.05404(19) Uani 1 1 d . . . H4N H 0.997(4) 0.538(2) 0.1748(10) 0.073(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0604(14) 0.0368(11) 0.0517(13) 0.0075(10) 0.0127(11) 0.0058(10) C2 0.0513(13) 0.0351(11) 0.0546(13) 0.0059(10) 0.0064(10) -0.0075(9) C3 0.0466(13) 0.0431(13) 0.0680(16) -0.0184(12) 0.0064(11) -0.0035(10) C4 0.0527(15) 0.0462(14) 0.104(2) 0.0148(15) 0.0093(15) -0.0073(12) C5 0.069(2) 0.103(3) 0.078(2) 0.039(2) 0.0311(17) 0.0115(19) C6 0.096(2) 0.080(2) 0.0510(16) 0.0083(15) 0.0224(16) 0.0180(18) C7 0.096(3) 0.107(3) 0.060(2) 0.0187(19) -0.0101(18) 0.004(2) C8 0.095(3) 0.114(3) 0.0580(19) 0.010(2) -0.0215(18) -0.012(2) C9 0.0441(19) 0.056(2) 0.077(3) -0.0196(19) -0.0140(17) 0.0034(16) C9' 0.027(5) 0.040(6) 0.048(6) -0.009(5) 0.005(4) 0.003(4) C10 0.0266(12) 0.0528(16) 0.172(4) 0.019(2) -0.0101(17) -0.0047(11) N1 0.0313(8) 0.0587(11) 0.0324(9) -0.0072(8) 0.0052(7) 0.0024(8) N2 0.0326(8) 0.0505(10) 0.0352(9) -0.0060(8) 0.0089(7) -0.0025(7) N3 0.0328(8) 0.0376(9) 0.0321(8) 0.0055(7) -0.0013(6) -0.0018(7) N4 0.0499(11) 0.0388(10) 0.0448(11) 0.0095(8) 0.0131(9) -0.0009(8) O1 0.0550(9) 0.0388(8) 0.0418(8) -0.0023(6) 0.0122(7) 0.0014(7) O2 0.0335(7) 0.0417(9) 0.0667(11) -0.0037(7) 0.0003(7) -0.0029(6) O3 0.0502(10) 0.0741(13) 0.0645(12) 0.0248(10) 0.0094(8) -0.0049(9) O4 0.0683(12) 0.0622(12) 0.0461(10) -0.0004(8) 0.0079(8) 0.0118(9) O5 0.0677(13) 0.0725(13) 0.0568(11) 0.0041(10) -0.0072(9) -0.0053(10) O6 0.0284(7) 0.0432(8) 0.0719(11) 0.0044(8) 0.0103(7) 0.0029(6) P1 0.0359(3) 0.0378(3) 0.0257(2) 0.00029(19) 0.00415(19) -0.0014(2) P2 0.0281(3) 0.0393(3) 0.0289(3) -0.00142(19) 0.00194(18) -0.00069(19) P3 0.0265(2) 0.0346(3) 0.0367(3) 0.0034(2) 0.00493(19) -0.00049(18) Cl1 0.0681(4) 0.0664(4) 0.0304(3) 0.0012(2) 0.0149(2) -0.0097(3) Cl2 0.0604(4) 0.0605(4) 0.0378(3) 0.0078(2) -0.0051(2) 0.0118(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.474(3) . ? C1 C2 1.520(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N4 1.467(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O2 1.436(3) . ? C3 C4 1.482(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O3 1.402(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O3 1.424(4) . ? C5 C6 1.460(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.421(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O4 1.419(4) . ? C7 C8 1.429(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O5 1.415(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.390(6) . ? C9 O5 1.483(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9' O5 1.284(11) . ? C9' C10 1.509(12) . ? C9' H9'1 0.9700 . ? C9' H9'2 0.9700 . ? C10 O6 1.441(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N1 P2 1.5845(18) . ? N1 P1 1.5879(18) . ? N2 P2 1.5714(17) . ? N2 P3 1.6073(18) . ? N3 P1 1.5756(18) . ? N3 P3 1.6019(18) . ? N4 P3 1.6345(19) . ? N4 H4N 0.933(10) . ? O1 P1 1.5841(17) . ? O2 P2 1.5654(16) . ? O6 P3 1.5714(16) . ? P1 Cl1 1.9997(7) . ? P1 P3 2.6535(7) . ? P2 Cl2 2.0345(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 115.17(19) . . ? O1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? O1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? N4 C2 C1 116.1(2) . . ? N4 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 . . ? N4 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? O2 C3 C4 111.5(2) . . ? O2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? O2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? O3 C4 C3 108.7(2) . . ? O3 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? O3 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.3 . . ? O3 C5 C6 109.3(3) . . ? O3 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? O4 C6 C5 109.8(3) . . ? O4 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O4 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O4 C7 C8 116.8(3) . . ? O4 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? O4 C7 H7B 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? O5 C8 C7 113.5(3) . . ? O5 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? O5 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 O5 110.7(3) . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? O5 C9' C10 115.5(7) . . ? O5 C9' H9'1 108.4 . . ? C10 C9' H9'1 108.4 . . ? O5 C9' H9'2 108.4 . . ? C10 C9' H9'2 108.4 . . ? H9'1 C9' H9'2 107.5 . . ? C9 C10 O6 114.4(3) . . ? C9 C10 C9' 39.2(5) . . ? O6 C10 C9' 119.4(5) . . ? C9 C10 H10A 108.7 . . ? O6 C10 H10A 108.7 . . ? C9' C10 H10A 70.6 . . ? C9 C10 H10B 108.7 . . ? O6 C10 H10B 108.7 . . ? C9' C10 H10B 129.9 . . ? H10A C10 H10B 107.6 . . ? P2 N1 P1 120.09(11) . . ? P2 N2 P3 117.04(11) . . ? P1 N3 P3 113.25(10) . . ? C2 N4 P3 123.99(16) . . ? C2 N4 H4N 113(2) . . ? P3 N4 H4N 121(2) . . ? C1 O1 P1 116.45(14) . . ? C3 O2 P2 125.62(15) . . ? C4 O3 C5 112.8(2) . . ? C7 O4 C6 113.9(3) . . ? C9' O5 C8 130.9(6) . . ? C9' O5 C9 40.6(5) . . ? C8 O5 C9 105.2(3) . . ? C10 O6 P3 122.46(19) . . ? N3 P1 O1 111.66(9) . . ? N3 P1 N1 117.35(9) . . ? O1 P1 N1 110.35(10) . . ? N3 P1 Cl1 109.00(7) . . ? O1 P1 Cl1 98.70(7) . . ? N1 P1 Cl1 108.09(7) . . ? N3 P1 P3 33.69(6) . . ? O1 P1 P3 107.85(6) . . ? N1 P1 P3 89.91(7) . . ? Cl1 P1 P3 140.34(3) . . ? O2 P2 N2 112.37(10) . . ? O2 P2 N1 111.12(10) . . ? N2 P2 N1 119.48(9) . . ? O2 P2 Cl2 96.81(7) . . ? N2 P2 Cl2 109.28(8) . . ? N1 P2 Cl2 105.02(8) . . ? O6 P3 N3 111.75(9) . . ? O6 P3 N2 102.14(10) . . ? N3 P3 N2 115.27(9) . . ? O6 P3 N4 109.09(10) . . ? N3 P3 N4 105.29(10) . . ? N2 P3 N4 113.34(11) . . ? O6 P3 P1 143.27(7) . . ? N3 P3 P1 33.06(6) . . ? N2 P3 P1 92.18(7) . . ? N4 P3 P1 95.40(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N4 83.4(3) . . . . ? O2 C3 C4 O3 -74.5(3) . . . . ? O3 C5 C6 O4 -71.5(4) . . . . ? O4 C7 C8 O5 -53.4(6) . . . . ? O5 C9 C10 O6 58.4(4) . . . . ? O5 C9 C10 C9' -48.9(7) . . . . ? O5 C9' C10 C9 64.4(8) . . . . ? O5 C9' C10 O6 -29.0(11) . . . . ? C1 C2 N4 P3 -64.0(3) . . . . ? C2 C1 O1 P1 -60.4(3) . . . . ? C4 C3 O2 P2 89.2(3) . . . . ? C3 C4 O3 C5 173.0(3) . . . . ? C6 C5 O3 C4 164.8(3) . . . . ? C8 C7 O4 C6 -68.3(5) . . . . ? C5 C6 O4 C7 -172.5(3) . . . . ? C10 C9' O5 C8 -116.5(8) . . . . ? C10 C9' O5 C9 -55.1(7) . . . . ? C7 C8 O5 C9' -170.0(7) . . . . ? C7 C8 O5 C9 153.7(4) . . . . ? C10 C9 O5 C9' 59.2(8) . . . . ? C10 C9 O5 C8 -164.2(3) . . . . ? C9 C10 O6 P3 86.7(3) . . . . ? C9' C10 O6 P3 130.5(6) . . . . ? P3 N3 P1 O1 -89.94(12) . . . . ? P3 N3 P1 N1 38.85(15) . . . . ? P3 N3 P1 Cl1 162.07(8) . . . . ? C1 O1 P1 N3 59.93(18) . . . . ? C1 O1 P1 N1 -72.47(18) . . . . ? C1 O1 P1 Cl1 174.46(15) . . . . ? C1 O1 P1 P3 24.29(17) . . . . ? P2 N1 P1 N3 -13.86(19) . . . . ? P2 N1 P1 O1 115.56(14) . . . . ? P2 N1 P1 Cl1 -137.54(12) . . . . ? P2 N1 P1 P3 6.51(13) . . . . ? C3 O2 P2 N2 21.5(2) . . . . ? C3 O2 P2 N1 -115.3(2) . . . . ? C3 O2 P2 Cl2 135.6(2) . . . . ? P3 N2 P2 O2 -141.96(12) . . . . ? P3 N2 P2 N1 -9.09(19) . . . . ? P3 N2 P2 Cl2 111.79(11) . . . . ? P1 N1 P2 O2 131.82(13) . . . . ? P1 N1 P2 N2 -1.6(2) . . . . ? P1 N1 P2 Cl2 -124.57(12) . . . . ? C10 O6 P3 N3 -61.1(2) . . . . ? C10 O6 P3 N2 175.1(2) . . . . ? C10 O6 P3 N4 54.9(3) . . . . ? C10 O6 P3 P1 -74.2(3) . . . . ? P1 N3 P3 O6 -165.65(10) . . . . ? P1 N3 P3 N2 -49.62(15) . . . . ? P1 N3 P3 N4 76.05(13) . . . . ? P2 N2 P3 O6 156.21(12) . . . . ? P2 N2 P3 N3 34.82(17) . . . . ? P2 N2 P3 N4 -86.59(15) . . . . ? P2 N2 P3 P1 10.24(12) . . . . ? C2 N4 P3 O6 -127.00(19) . . . . ? C2 N4 P3 N3 -6.9(2) . . . . ? C2 N4 P3 N2 119.94(19) . . . . ? C2 N4 P3 P1 25.2(2) . . . . ? N3 P1 P3 O6 22.64(16) . . . . ? O1 P1 P3 O6 125.10(13) . . . . ? N1 P1 P3 O6 -123.50(14) . . . . ? Cl1 P1 P3 O6 -4.50(13) . . . . ? O1 P1 P3 N3 102.47(13) . . . . ? N1 P1 P3 N3 -146.14(14) . . . . ? Cl1 P1 P3 N3 -27.14(12) . . . . ? N3 P1 P3 N2 136.41(14) . . . . ? O1 P1 P3 N2 -121.12(10) . . . . ? N1 P1 P3 N2 -9.72(10) . . . . ? Cl1 P1 P3 N2 109.28(9) . . . . ? N3 P1 P3 N4 -109.89(14) . . . . ? O1 P1 P3 N4 -7.43(10) . . . . ? N1 P1 P3 N4 103.97(11) . . . . ? Cl1 P1 P3 N4 -137.03(9) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.867 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.065 # Attachment '7b.cif' data_7b _database_code_depnum_ccdc_archive 'CCDC 242927' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Cl3 N4 O2 P3' _chemical_formula_weight 345.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.340(7) _cell_length_b 9.123(10) _cell_length_c 14.023(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.23(6) _cell_angle_gamma 90.00 _cell_volume 1312.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27640 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.055 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.8168 _exptl_absorpt_correction_T_max 0.9691 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 14903 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2979 _reflns_number_gt 2168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.8325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2979 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.012 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6440(3) -0.0709(4) 0.6168(3) 0.0440(8) Uani 1 1 d . . . H1A H 0.6723 -0.0671 0.6868 0.053 Uiso 1 1 calc R . . H1B H 0.6192 0.0293 0.5943 0.053 Uiso 1 1 calc R . . C2 C 0.7528(3) -0.1266(4) 0.5657(3) 0.0468(8) Uani 1 1 d . . . H2A H 0.7768 -0.2258 0.5883 0.070 Uiso 1 1 calc R . . H2B H 0.8284 -0.0617 0.5789 0.070 Uiso 1 1 calc R . . H2C H 0.7244 -0.1290 0.4963 0.070 Uiso 1 1 calc R . . C3 C 0.4803(3) -0.1314(3) 0.8621(2) 0.0387(7) Uani 1 1 d . . . H3A H 0.5193 -0.0338 0.8540 0.046 Uiso 1 1 calc R . . H3B H 0.5339 -0.1806 0.9163 0.046 Uiso 1 1 calc R . . C4 C 0.3446(3) -0.1095(4) 0.8892(2) 0.0429(7) Uani 1 1 d . . . H4A H 0.2951 -0.2019 0.8768 0.051 Uiso 1 1 calc R . . H4B H 0.3516 -0.0896 0.9591 0.051 Uiso 1 1 calc R . . N1 N 0.3704(2) -0.0068(3) 0.67703(17) 0.0329(5) Uani 1 1 d . . . N2 N 0.1369(2) -0.1280(3) 0.69435(19) 0.0390(6) Uani 1 1 d . . . N3 N 0.3202(2) -0.2849(3) 0.61704(19) 0.0391(6) Uani 1 1 d . . . N4 N 0.4890(3) -0.2171(3) 0.77437(19) 0.0369(6) Uani 1 1 d . . . O1 O 0.53292(19) -0.1696(2) 0.59649(15) 0.0380(5) Uani 1 1 d . . . O2 O 0.2700(2) 0.0104(2) 0.83762(14) 0.0376(5) Uani 1 1 d . . . P1 P 0.42580(7) -0.16878(9) 0.66605(6) 0.0329(2) Uani 1 1 d . . . P2 P 0.23960(7) -0.00122(9) 0.72477(5) 0.0334(2) Uani 1 1 d . . . P3 P 0.17430(7) -0.26089(9) 0.63137(6) 0.0353(2) Uani 1 1 d . . . Cl1 Cl 0.15684(7) 0.19229(8) 0.69595(6) 0.0412(2) Uani 1 1 d . . . Cl2 Cl 0.06535(8) -0.25448(11) 0.50186(6) 0.0557(3) Uani 1 1 d . . . Cl3 Cl 0.10384(8) -0.44171(9) 0.68597(7) 0.0526(2) Uani 1 1 d . . . H4N H 0.515(3) -0.292(4) 0.783(2) 0.032(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0360(16) 0.0463(19) 0.050(2) -0.0034(15) 0.0068(14) -0.0065(14) C2 0.0405(16) 0.057(2) 0.0449(19) 0.0076(16) 0.0119(15) 0.0007(16) C3 0.0468(17) 0.0376(17) 0.0308(16) 0.0018(13) 0.0012(13) 0.0014(14) C4 0.0536(19) 0.0427(18) 0.0332(17) 0.0058(14) 0.0093(15) 0.0035(15) N1 0.0337(12) 0.0331(13) 0.0319(13) 0.0000(10) 0.0039(10) -0.0006(10) N2 0.0351(12) 0.0407(15) 0.0422(15) -0.0062(12) 0.0090(11) -0.0010(11) N3 0.0352(13) 0.0380(14) 0.0437(15) -0.0089(12) 0.0043(11) 0.0012(11) N4 0.0411(14) 0.0310(15) 0.0378(15) 0.0037(11) 0.0026(12) 0.0076(12) O1 0.0326(10) 0.0455(12) 0.0365(12) -0.0027(9) 0.0063(9) 0.0004(9) O2 0.0466(11) 0.0352(11) 0.0315(11) 0.0010(9) 0.0064(9) 0.0051(10) P1 0.0309(4) 0.0348(4) 0.0330(4) -0.0015(3) 0.0040(3) 0.0009(3) P2 0.0353(4) 0.0317(4) 0.0334(4) -0.0010(3) 0.0054(3) 0.0015(3) P3 0.0314(4) 0.0361(4) 0.0380(4) -0.0042(3) 0.0032(3) 0.0001(3) Cl1 0.0427(4) 0.0354(4) 0.0449(5) -0.0001(3) 0.0025(3) 0.0071(3) Cl2 0.0410(4) 0.0800(7) 0.0436(5) -0.0099(4) -0.0050(4) 0.0078(4) Cl3 0.0474(5) 0.0369(4) 0.0753(6) 0.0006(4) 0.0144(4) -0.0038(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.459(4) . ? C1 C2 1.496(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N4 1.470(4) . ? C3 C4 1.513(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O2 1.474(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N1 P2 1.583(3) . ? N1 P1 1.599(3) . ? N2 P3 1.576(3) . ? N2 P2 1.592(3) . ? N3 P3 1.563(3) . ? N3 P1 1.611(3) . ? N4 P1 1.637(3) . ? N4 H4N 0.73(3) . ? O1 P1 1.565(2) . ? O2 P2 1.578(2) . ? P1 P2 2.6684(18) . ? P2 Cl1 1.981(2) . ? P3 Cl3 1.9947(19) . ? P3 Cl2 2.0140(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 108.5(3) . . ? O1 C1 H1A 110.0 . . ? C2 C1 H1A 110.0 . . ? O1 C1 H1B 110.0 . . ? C2 C1 H1B 110.0 . . ? H1A C1 H1B 108.4 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N4 C3 C4 115.9(3) . . ? N4 C3 H3A 108.3 . . ? C4 C3 H3A 108.3 . . ? N4 C3 H3B 108.3 . . ? C4 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? O2 C4 C3 114.8(2) . . ? O2 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? O2 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? P2 N1 P1 113.94(15) . . ? P3 N2 P2 120.43(16) . . ? P3 N3 P1 117.81(16) . . ? C3 N4 P1 125.0(2) . . ? C3 N4 H4N 115(3) . . ? P1 N4 H4N 120(3) . . ? C1 O1 P1 118.51(19) . . ? C4 O2 P2 117.95(19) . . ? O1 P1 N1 110.76(12) . . ? O1 P1 N3 103.03(13) . . ? N1 P1 N3 114.62(14) . . ? O1 P1 N4 110.24(14) . . ? N1 P1 N4 105.42(14) . . ? N3 P1 N4 112.87(15) . . ? O1 P1 P2 142.14(10) . . ? N1 P1 P2 32.84(8) . . ? N3 P1 P2 91.82(11) . . ? N4 P1 P2 95.02(11) . . ? O2 P2 N1 110.68(13) . . ? O2 P2 N2 111.08(13) . . ? N1 P2 N2 116.09(13) . . ? O2 P2 Cl1 99.87(9) . . ? N1 P2 Cl1 108.20(10) . . ? N2 P2 Cl1 109.66(12) . . ? O2 P2 P1 106.69(9) . . ? N1 P2 P1 33.21(10) . . ? N2 P2 P1 89.08(11) . . ? Cl1 P2 P1 139.24(5) . . ? N3 P3 N2 119.25(14) . . ? N3 P3 Cl3 109.82(12) . . ? N2 P3 Cl3 107.08(13) . . ? N3 P3 Cl2 109.14(12) . . ? N2 P3 Cl2 109.51(11) . . ? Cl3 P3 Cl2 100.38(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.318 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.098 # Attachment '8b.cif' data_8b _database_code_depnum_ccdc_archive 'CCDC 242928' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Cl3 N5 O P3' _chemical_formula_weight 370.47 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.231(3) _cell_length_b 17.426(4) _cell_length_c 9.8503(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.76(3) _cell_angle_gamma 90.00 _cell_volume 1408.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3294 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8582 _exptl_absorpt_correction_T_max 0.9710 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 18678 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3220 _reflns_number_gt 2626 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+11.2172P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3220 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1126 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.1701 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.272 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H4N H 0.146(9) -0.030(4) -0.041(8) 0.03(2) Uiso 1 1 d . . . C1 C 0.3923(10) 0.0782(4) -0.1569(8) 0.0406(19) Uani 1 1 d . . . H1A H 0.5089 0.0637 -0.1519 0.049 Uiso 1 1 calc R . . H1B H 0.3701 0.1132 -0.2354 0.049 Uiso 1 1 calc R . . C2 C 0.2915(9) 0.0094(5) -0.1768(7) 0.0416(19) Uani 1 1 d . . . H2A H 0.2199 0.0134 -0.2624 0.050 Uiso 1 1 calc R . . H2B H 0.3611 -0.0367 -0.1821 0.050 Uiso 1 1 calc R . . C3 C -0.2601(8) 0.2111(4) 0.0650(7) 0.0274(14) Uani 1 1 d . . . H3A H -0.3147 0.1699 0.0089 0.033 Uiso 1 1 calc R . . H3B H -0.1865 0.2398 0.0088 0.033 Uiso 1 1 calc R . . C4 C -0.3844(8) 0.2643(4) 0.1207(8) 0.0346(17) Uani 1 1 d . . . H4A H -0.3406 0.3170 0.1329 0.042 Uiso 1 1 calc R . . H4B H -0.4861 0.2661 0.0596 0.042 Uiso 1 1 calc R . . C5 C -0.4137(8) 0.2281(4) 0.2565(7) 0.0293(15) Uani 1 1 d . . . H5A H -0.4599 0.2660 0.3176 0.035 Uiso 1 1 calc R . . H5B H -0.4892 0.1840 0.2440 0.035 Uiso 1 1 calc R . . C6 C -0.2463(8) 0.2022(4) 0.3137(7) 0.0287(15) Uani 1 1 d . . . H6A H -0.1854 0.2445 0.3616 0.034 Uiso 1 1 calc R . . H6B H -0.2536 0.1584 0.3770 0.034 Uiso 1 1 calc R . . N1 N 0.0659(6) 0.1245(3) 0.0536(5) 0.0251(12) Uani 1 1 d . . . N2 N 0.0819(6) 0.1208(3) 0.3317(5) 0.0243(12) Uani 1 1 d . . . N3 N 0.3062(7) 0.0475(3) 0.1923(6) 0.0292(13) Uani 1 1 d . . . N4 N 0.1956(8) 0.0040(4) -0.0621(6) 0.0351(15) Uani 1 1 d . . . N5 N -0.1689(6) 0.1788(3) 0.1878(5) 0.0245(12) Uani 1 1 d . . . O1 O 0.3581(6) 0.1171(3) -0.0331(5) 0.0332(11) Uani 1 1 d . . . P1 P 0.22530(19) 0.07370(9) 0.04577(17) 0.0220(4) Uani 1 1 d . . . P2 P 0.02387(19) 0.16284(9) 0.19201(16) 0.0210(4) Uani 1 1 d . . . P3 P 0.2260(2) 0.06193(9) 0.32835(17) 0.0231(4) Uani 1 1 d . . . Cl1 Cl 0.13505(19) 0.26883(9) 0.19982(17) 0.0285(4) Uani 1 1 d . . . Cl2 Cl 0.1554(2) -0.03836(10) 0.40374(19) 0.0365(4) Uani 1 1 d . . . Cl3 Cl 0.4033(2) 0.09094(10) 0.47147(17) 0.0322(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(5) 0.028(4) 0.046(5) 0.008(3) 0.028(4) 0.011(3) C2 0.030(4) 0.071(6) 0.024(4) -0.012(4) 0.007(3) -0.012(4) C3 0.019(3) 0.032(4) 0.029(4) 0.003(3) -0.003(3) 0.003(3) C4 0.026(4) 0.034(4) 0.045(4) 0.013(3) 0.007(3) 0.008(3) C5 0.020(3) 0.035(4) 0.034(4) 0.004(3) 0.008(3) 0.005(3) C6 0.020(3) 0.037(4) 0.029(4) -0.006(3) 0.007(3) 0.001(3) N1 0.021(3) 0.032(3) 0.022(3) -0.007(2) 0.001(2) 0.005(2) N2 0.026(3) 0.027(3) 0.021(3) 0.002(2) 0.004(2) 0.008(2) N3 0.026(3) 0.037(3) 0.026(3) 0.007(2) 0.009(2) 0.013(2) N4 0.050(4) 0.026(3) 0.033(3) -0.004(3) 0.025(3) -0.009(3) N5 0.021(3) 0.024(3) 0.029(3) -0.001(2) 0.003(2) 0.000(2) O1 0.032(3) 0.045(3) 0.023(2) 0.000(2) 0.0070(19) -0.018(2) P1 0.0197(8) 0.0204(8) 0.0268(9) -0.0001(7) 0.0070(6) -0.0004(6) P2 0.0188(8) 0.0219(8) 0.0220(8) -0.0030(6) 0.0006(6) 0.0035(6) P3 0.0229(9) 0.0235(8) 0.0239(8) 0.0033(7) 0.0075(6) 0.0054(7) Cl1 0.0235(8) 0.0255(8) 0.0364(9) -0.0038(7) 0.0022(6) -0.0019(6) Cl2 0.0394(10) 0.0279(9) 0.0431(10) 0.0115(8) 0.0092(8) 0.0015(7) Cl3 0.0261(8) 0.0388(9) 0.0312(9) 0.0046(7) 0.0002(6) 0.0054(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.443(8) . ? C1 C2 1.462(11) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N4 1.434(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N5 1.481(8) . ? C3 C4 1.517(9) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.517(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.514(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N5 1.498(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 P2 1.582(5) . ? N1 P1 1.590(5) . ? N2 P3 1.570(5) . ? N2 P2 1.597(5) . ? N3 P3 1.563(5) . ? N3 P1 1.605(6) . ? N4 P1 1.619(6) . ? N4 H4N 0.75(8) . ? N5 P2 1.608(5) . ? O1 P1 1.585(5) . ? P2 Cl1 2.060(2) . ? P3 Cl2 2.004(2) . ? P3 Cl3 2.007(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 110.5(6) . . ? O1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? N4 C2 C1 106.9(6) . . ? N4 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? N4 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.6 . . ? N5 C3 C4 104.4(5) . . ? N5 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? N5 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C5 C4 C3 103.0(5) . . ? C5 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? C5 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? C6 C5 C4 104.3(5) . . ? C6 C5 H5A 110.9 . . ? C4 C5 H5A 110.9 . . ? C6 C5 H5B 110.9 . . ? C4 C5 H5B 110.9 . . ? H5A C5 H5B 108.9 . . ? N5 C6 C5 102.1(5) . . ? N5 C6 H6A 111.3 . . ? C5 C6 H6A 111.3 . . ? N5 C6 H6B 111.3 . . ? C5 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? P2 N1 P1 121.2(3) . . ? P3 N2 P2 117.0(3) . . ? P3 N3 P1 123.5(3) . . ? C2 N4 P1 113.9(5) . . ? C2 N4 H4N 128(6) . . ? P1 N4 H4N 117(6) . . ? C3 N5 C6 110.5(5) . . ? C3 N5 P2 121.3(4) . . ? C6 N5 P2 120.9(4) . . ? C1 O1 P1 112.4(4) . . ? O1 P1 N1 111.4(3) . . ? O1 P1 N3 109.0(3) . . ? N1 P1 N3 113.4(3) . . ? O1 P1 N4 96.2(3) . . ? N1 P1 N4 111.7(3) . . ? N3 P1 N4 113.9(3) . . ? N1 P2 N2 118.5(3) . . ? N1 P2 N5 109.7(3) . . ? N2 P2 N5 109.0(3) . . ? N1 P2 Cl1 106.4(2) . . ? N2 P2 Cl1 106.2(2) . . ? N5 P2 Cl1 106.3(2) . . ? N3 P3 N2 119.8(3) . . ? N3 P3 Cl2 109.5(2) . . ? N2 P3 Cl2 108.6(2) . . ? N3 P3 Cl3 108.0(2) . . ? N2 P3 Cl3 109.1(2) . . ? Cl2 P3 Cl3 100.12(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.507 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.120 data_5b _database_code_depnum_ccdc_archive 'CCDC 242930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cl2 N3 O7 P3' _chemical_formula_weight 458.10 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.66570(10) _cell_length_b 13.9489(3) _cell_length_c 15.3589(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.2150(10) _cell_angle_gamma 90.00 _cell_volume 1832.58(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 33790 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94705 _exptl_absorpt_correction_T_max 0.98886 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20942 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4185 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+5.5991P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4185 _refine_ls_number_parameters 281 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.014 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1' C -0.2621(11) 0.8594(7) 0.1414(5) 0.0253(18) Uani 0.50 1 d P A 1 H1'1 H -0.3294 0.9083 0.1632 0.030 Uiso 0.50 1 calc PR A 1 H1'2 H -0.2205 0.8864 0.0902 0.030 Uiso 0.50 1 calc PR A 1 C2' C -0.3547(8) 0.7708(6) 0.1146(5) 0.0310(14) Uani 0.50 1 d P A 1 H2'1 H -0.4017 0.7478 0.1654 0.037 Uiso 0.50 1 calc PR A 1 H2'2 H -0.4411 0.7873 0.0666 0.037 Uiso 0.50 1 calc PR A 1 C1 C -0.2671(11) 0.8496(8) 0.1857(10) 0.054(3) Uani 0.50 1 d P A 2 H1A H -0.2872 0.9194 0.1865 0.065 Uiso 0.50 1 calc PR A 2 H1B H -0.3382 0.8169 0.2206 0.065 Uiso 0.50 1 calc PR A 2 C2 C -0.2915(9) 0.8130(6) 0.0935(8) 0.057(3) Uani 0.50 1 d P A 2 H2A H -0.2140 0.8432 0.0612 0.068 Uiso 0.50 1 calc PR A 2 H2B H -0.3970 0.8321 0.0638 0.068 Uiso 0.50 1 calc PR A 2 C3 C -0.2236(10) 0.7138(6) -0.0006(4) 0.0312(14) Uani 0.50 1 d P A 1 H3A H -0.1649 0.7746 -0.0019 0.037 Uiso 0.50 1 calc PR A 1 H3B H -0.3170 0.7174 -0.0470 0.037 Uiso 0.50 1 calc PR A 1 C4 C -0.1208(13) 0.6309(6) -0.0213(7) 0.034(2) Uani 0.50 1 d P A 1 H4A H -0.1801 0.5700 -0.0234 0.040 Uiso 0.50 1 calc PR A 1 H4B H -0.0882 0.6410 -0.0795 0.040 Uiso 0.50 1 calc PR A 1 C3' C -0.2775(10) 0.6701(7) 0.0119(5) 0.045(2) Uani 0.50 1 d P A 2 H3'1 H -0.3553 0.7052 -0.0306 0.054 Uiso 0.50 1 calc PR A 2 H3'2 H -0.3087 0.6018 0.0109 0.054 Uiso 0.50 1 calc PR A 2 C4' C -0.1229(16) 0.6788(12) -0.0142(7) 0.061(4) Uani 0.50 1 d P A 2 H4'1 H -0.0946 0.7476 -0.0136 0.074 Uiso 0.50 1 calc PR A 2 H4'2 H -0.1301 0.6559 -0.0757 0.074 Uiso 0.50 1 calc PR A 2 C5' C 0.1358(5) 0.6838(4) 0.0241(3) 0.0455(16) Uani 0.787(10) 1 d P A 1 H5'1 H 0.1176 0.7524 0.0358 0.055 Uiso 0.787(10) 1 calc PR A 1 H5'2 H 0.1515 0.6767 -0.0380 0.055 Uiso 0.787(10) 1 calc PR A 1 C6' C 0.2759(9) 0.6469(10) 0.0859(5) 0.108(4) Uani 0.787(10) 1 d P A 1 H6'1 H 0.2754 0.5759 0.0872 0.129 Uiso 0.787(10) 1 calc PR A 1 H6'2 H 0.3738 0.6686 0.0665 0.129 Uiso 0.787(10) 1 calc PR A 1 C5 C 0.1443(15) 0.5851(10) 0.0355(11) 0.037(5) Uani 0.213(10) 1 d PD A 2 H5A H 0.1524 0.5666 -0.0258 0.044 Uiso 0.213(10) 1 calc PR A 2 H5B H 0.1649 0.5285 0.0745 0.044 Uiso 0.213(10) 1 calc PR A 2 C6 C 0.2528(16) 0.6696(8) 0.0679(10) 0.008(3) Uani 0.213(10) 1 d PDU A 2 H6A H 0.3580 0.6576 0.0529 0.010 Uiso 0.213(10) 1 calc PR A 2 H6B H 0.2114 0.7290 0.0374 0.010 Uiso 0.213(10) 1 calc PR A 2 C7 C 0.3770(5) 0.6365(3) 0.2321(3) 0.0458(9) Uani 1 1 d . A . H7A H 0.4823 0.6413 0.2152 0.055 Uiso 1 1 calc R . . H7B H 0.3499 0.5678 0.2356 0.055 Uiso 1 1 calc R . . C8 C 0.3762(4) 0.6832(2) 0.3185(2) 0.0322(7) Uani 1 1 d . . . H8A H 0.2682 0.6844 0.3319 0.039 Uiso 1 1 calc R . . H8B H 0.4419 0.6460 0.3653 0.039 Uiso 1 1 calc R . . C9 C 0.0545(4) 1.0815(2) 0.2615(2) 0.0285(7) Uani 1 1 d . A . H9A H 0.1536 1.0677 0.3013 0.034 Uiso 1 1 calc R . . H9B H 0.0010 1.1337 0.2887 0.034 Uiso 1 1 calc R . . C10 C 0.0931(4) 1.1169(2) 0.1742(2) 0.0282(6) Uani 1 1 d . . . H10A H 0.0023 1.1041 0.1278 0.034 Uiso 1 1 calc R . . H10B H 0.1076 1.1873 0.1780 0.034 Uiso 1 1 calc R . . N1 N 0.1563(3) 0.85439(19) 0.29705(16) 0.0261(5) Uani 1 1 d . . . N2 N 0.3777(3) 0.9184(2) 0.20437(17) 0.0276(6) Uani 1 1 d . A . N3 N 0.0728(3) 0.91675(17) 0.13002(15) 0.0195(5) Uani 1 1 d . A . O1 O -0.1198(3) 0.83092(16) 0.21839(18) 0.0364(6) Uani 1 1 d . . . O2 O -0.2760(3) 0.70381(19) 0.08865(18) 0.0424(6) Uani 1 1 d . . . O3 O 0.0051(4) 0.6260(3) 0.04134(18) 0.0600(9) Uani 1 1 d . . . O4 O 0.2657(3) 0.6834(2) 0.16865(16) 0.0403(6) Uani 1 1 d . . . O5 O 0.4350(3) 0.77965(18) 0.31758(19) 0.0457(7) Uani 1 1 d . . . O6 O -0.0435(3) 0.99626(15) 0.25581(15) 0.0284(5) Uani 1 1 d . . . O7 O 0.2327(2) 1.07426(15) 0.14675(15) 0.0294(5) Uani 1 1 d . A . P1 P 0.02329(9) 0.89869(5) 0.22445(5) 0.02133(18) Uani 1 1 d . A . P2 P 0.33352(10) 0.87070(6) 0.29063(5) 0.0280(2) Uani 1 1 d . . . P3 P 0.24021(8) 0.96170(5) 0.13531(5) 0.02027(17) Uani 1 1 d . . . Cl1 Cl 0.42635(17) 0.95655(8) 0.39222(6) 0.0673(4) Uani 1 1 d . . . Cl2 Cl 0.30739(10) 0.95055(6) 0.01703(5) 0.0377(2) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1' 0.015(3) 0.028(4) 0.033(4) 0.002(4) 0.001(3) 0.001(3) C2' 0.022(3) 0.035(4) 0.035(4) -0.003(3) 0.004(3) -0.004(3) C1 0.013(4) 0.033(5) 0.115(10) -0.015(7) 0.003(6) 0.002(3) C2 0.025(4) 0.018(4) 0.113(8) 0.020(5) -0.035(5) -0.010(3) C3 0.032(4) 0.037(4) 0.023(3) 0.007(3) 0.001(3) -0.003(3) C4 0.036(4) 0.035(4) 0.029(4) -0.007(4) 0.001(3) 0.007(4) C3' 0.044(5) 0.044(5) 0.037(4) 0.014(4) -0.021(3) -0.013(4) C4' 0.057(7) 0.104(11) 0.022(5) 0.020(7) 0.001(4) -0.016(9) C5' 0.035(3) 0.084(4) 0.021(2) -0.006(2) 0.0133(18) -0.010(2) C6' 0.051(4) 0.233(12) 0.035(4) -0.032(5) -0.005(3) 0.067(6) C5 0.018(7) 0.055(11) 0.036(9) -0.006(7) 0.003(6) 0.006(7) C6 0.009(3) 0.008(3) 0.008(3) 0.0010(10) 0.0021(11) 0.0003(10) C7 0.036(2) 0.052(2) 0.052(2) -0.0012(18) 0.0144(17) 0.0134(17) C8 0.0313(17) 0.0299(16) 0.0363(17) 0.0145(14) 0.0085(14) 0.0023(13) C9 0.0350(17) 0.0213(15) 0.0313(16) -0.0077(12) 0.0116(13) -0.0048(12) C10 0.0290(16) 0.0232(15) 0.0336(16) 0.0002(12) 0.0094(13) 0.0024(12) N1 0.0341(14) 0.0276(13) 0.0186(12) 0.0021(10) 0.0097(10) -0.0009(11) N2 0.0166(12) 0.0352(14) 0.0303(13) 0.0095(11) 0.0021(10) 0.0002(10) N3 0.0158(11) 0.0246(12) 0.0179(11) -0.0026(9) 0.0019(9) 0.0010(9) O1 0.0244(11) 0.0261(11) 0.0638(16) -0.0087(11) 0.0228(11) -0.0076(9) O2 0.0323(13) 0.0362(14) 0.0541(17) 0.0182(12) -0.0074(11) -0.0098(11) O3 0.0510(18) 0.093(3) 0.0306(14) 0.0015(15) -0.0092(12) -0.0029(17) O4 0.0287(12) 0.0610(17) 0.0333(13) -0.0120(12) 0.0111(10) -0.0001(11) O5 0.0296(13) 0.0351(14) 0.0637(18) 0.0219(12) -0.0191(12) -0.0048(10) O6 0.0302(11) 0.0232(11) 0.0361(12) -0.0070(9) 0.0179(9) -0.0034(9) O7 0.0257(11) 0.0231(11) 0.0420(13) 0.0040(9) 0.0138(9) -0.0006(8) P1 0.0211(4) 0.0212(4) 0.0239(4) -0.0033(3) 0.0106(3) -0.0031(3) P2 0.0298(4) 0.0283(4) 0.0224(4) 0.0072(3) -0.0065(3) -0.0051(3) P3 0.0184(3) 0.0240(4) 0.0195(3) 0.0051(3) 0.0063(3) 0.0019(3) Cl1 0.1085(10) 0.0493(6) 0.0310(5) 0.0094(4) -0.0292(5) -0.0404(6) Cl2 0.0462(5) 0.0422(5) 0.0306(4) 0.0136(3) 0.0244(4) 0.0152(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1' C2' 1.495(12) . ? C1' O1 1.615(9) . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C2' O2 1.258(7) . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C1 O1 1.320(10) . ? C1 C2 1.489(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.532(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O2 1.518(8) . ? C3 C4 1.525(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.335(11) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3' O2 1.267(9) . ? C3' C4' 1.464(16) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' O3 1.483(14) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' O3 1.449(6) . ? C5' C6' 1.507(9) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' O4 1.385(7) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C5 O3 1.350(15) . ? C5 C6 1.5404(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O4 1.546(15) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O4 1.417(5) . ? C7 C8 1.480(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O5 1.439(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O6 1.456(4) . ? C9 C10 1.515(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O7 1.470(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N1 P2 1.571(3) . ? N1 P1 1.594(3) . ? N2 P3 1.583(3) . ? N2 P2 1.583(3) . ? N3 P3 1.570(2) . ? N3 P1 1.597(2) . ? O1 P1 1.550(2) . ? O5 P2 1.562(3) . ? O6 P1 1.584(2) . ? O7 P3 1.582(2) . ? P1 P3 2.6467(10) . ? P2 Cl1 2.0282(12) . ? P3 Cl2 2.0005(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2' C1' O1 108.1(6) . . ? C2' C1' H1'1 110.1 . . ? O1 C1' H1'1 110.1 . . ? C2' C1' H1'2 110.1 . . ? O1 C1' H1'2 110.1 . . ? H1'1 C1' H1'2 108.4 . . ? O2 C2' C1' 114.0(6) . . ? O2 C2' H2'1 108.7 . . ? C1' C2' H2'1 108.7 . . ? O2 C2' H2'2 108.7 . . ? C1' C2' H2'2 108.7 . . ? H2'1 C2' H2'2 107.6 . . ? O1 C1 C2 106.0(8) . . ? 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 . . ? C1 C2 O2 112.7(7) . . ? C1 C2 H2A 109.0 . . ? O2 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? O2 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O2 C3 C4 112.8(6) . . ? O2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? O2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? O3 C4 C3 109.0(7) . . ? O3 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? O3 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? O2 C3' C4' 110.5(8) . . ? O2 C3' H3'1 109.5 . . ? C4' C3' H3'1 109.5 . . ? O2 C3' H3'2 109.6 . . ? C4' C3' H3'2 109.5 . . ? H3'1 C3' H3'2 108.1 . . ? C3' C4' O3 115.8(8) . . ? C3' C4' H4'1 108.3 . . ? O3 C4' H4'1 108.3 . . ? C3' C4' H4'2 108.3 . . ? O3 C4' H4'2 108.3 . . ? H4'1 C4' H4'2 107.4 . . ? O3 C5' C6' 105.6(6) . . ? O3 C5' H5'1 110.6 . . ? C6' C5' H5'1 110.6 . . ? O3 C5' H5'2 110.6 . . ? C6' C5' H5'2 110.6 . . ? H5'1 C5' H5'2 108.7 . . ? O4 C6' C5' 106.8(6) . . ? O4 C6' H6'1 110.3 . . ? C5' C6' H6'1 110.4 . . ? O4 C6' H6'2 110.4 . . ? C5' C6' H6'2 110.4 . . ? H6'1 C6' H6'2 108.6 . . ? O3 C5 C6 99.2(10) . . ? O3 C5 H5A 112.0 . . ? C6 C5 H5A 112.0 . . ? O3 C5 H5B 111.9 . . ? C6 C5 H5B 111.9 . . ? H5A C5 H5B 109.6 . . ? O4 C6 C5 111.2(10) . . ? O4 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O4 C6 H6B 109.4 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? O4 C7 C8 108.2(3) . . ? O4 C7 H7A 110.1 . . ? C8 C7 H7A 110.1 . . ? O4 C7 H7B 110.1 . . ? C8 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? O5 C8 C7 110.5(3) . . ? O5 C8 H8A 109.6 . . ? C7 C8 H8A 109.5 . . ? O5 C8 H8B 109.6 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O6 C9 C10 115.0(3) . . ? O6 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? O6 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O7 C10 C9 115.5(3) . . ? O7 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? O7 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? P2 N1 P1 120.30(15) . . ? P3 N2 P2 117.68(15) . . ? P3 N3 P1 113.36(14) . . ? C1 O1 P1 128.2(5) . . ? C1 O1 C1' 25.2(6) . . ? P1 O1 C1' 113.8(4) . . ? C2' O2 C3' 130.1(5) . . ? C2' O2 C3 118.2(5) . . ? C3' O2 C3 32.2(4) . . ? C2' O2 C2 35.9(5) . . ? C3' O2 C2 115.2(6) . . ? C3 O2 C2 89.6(6) . . ? C4 O3 C5 127.5(8) . . ? C4 O3 C5' 114.3(6) . . ? C5 O3 C5' 59.4(6) . . ? C4 O3 C4' 27.2(5) . . ? C5 O3 C4' 140.0(9) . . ? C5' O3 C4' 98.8(6) . . ? C6' O4 C7 108.9(4) . . ? C6' O4 C6 16.4(7) . . ? C7 O4 C6 124.3(6) . . ? C8 O5 P2 125.3(2) . . ? C9 O6 P1 118.82(18) . . ? C10 O7 P3 118.95(18) . . ? O1 P1 O6 102.38(12) . . ? O1 P1 N1 106.71(14) . . ? O6 P1 N1 112.26(13) . . ? O1 P1 N3 111.75(14) . . ? O6 P1 N3 107.76(12) . . ? N1 P1 N3 115.26(13) . . ? O1 P1 P3 143.05(10) . . ? O6 P1 P3 101.32(8) . . ? N1 P1 P3 89.81(10) . . ? N3 P1 P3 33.00(8) . . ? O5 P2 N1 112.32(14) . . ? O5 P2 N2 111.21(16) . . ? N1 P2 N2 118.88(13) . . ? O5 P2 Cl1 98.00(11) . . ? N1 P2 Cl1 107.98(11) . . ? N2 P2 Cl1 106.06(11) . . ? N3 P3 N2 118.16(13) . . ? N3 P3 O7 110.36(12) . . ? N2 P3 O7 110.16(14) . . ? N3 P3 Cl2 108.83(10) . . ? N2 P3 Cl2 106.36(11) . . ? O7 P3 Cl2 101.60(9) . . ? N3 P3 P1 33.64(8) . . ? N2 P3 P1 92.70(10) . . ? O7 P3 P1 103.12(8) . . ? Cl2 P3 P1 141.08(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.296 _refine_diff_density_min -1.499 _refine_diff_density_rms 0.089 # Attachment '6a.CIF' data_6a _database_code_depnum_ccdc_archive 'CCDC 242931' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cl2 N3 O7 P3' _chemical_formula_weight 458.10 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9956(2) _cell_length_b 15.7971(5) _cell_length_c 14.8388(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.751(2) _cell_angle_gamma 90.00 _cell_volume 1834.97(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5.11 _cell_measurement_theta_max 23.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9140 _exptl_absorpt_correction_T_max 0.9618 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 24562 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4191 _reflns_number_gt 3318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+1.4026P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4191 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0498(3) 0.31891(15) 0.35217(15) 0.0221(5) Uani 1 1 d . . . H1A H 1.1091 0.3020 0.4148 0.027 Uiso 1 1 calc R . . H1B H 1.0652 0.3805 0.3447 0.027 Uiso 1 1 calc R . . C2 C 1.1179(3) 0.27005(14) 0.28029(15) 0.0211(5) Uani 1 1 d . . . H2A H 1.0997 0.3016 0.2215 0.025 Uiso 1 1 calc R . . H2B H 1.2414 0.2584 0.3010 0.025 Uiso 1 1 calc R . . C3 C 0.3801(3) 0.10398(14) 0.44576(15) 0.0210(5) Uani 1 1 d . . . H3A H 0.3323 0.0547 0.4731 0.025 Uiso 1 1 calc R . . H3B H 0.3060 0.1163 0.3852 0.025 Uiso 1 1 calc R . . C4 C 0.3878(3) 0.17927(14) 0.50774(15) 0.0219(5) Uani 1 1 d . . . H4A H 0.2741 0.1904 0.5219 0.026 Uiso 1 1 calc R . . H4B H 0.4703 0.1692 0.5662 0.026 Uiso 1 1 calc R . . C5 C 0.4666(3) 0.32478(14) 0.51269(15) 0.0217(5) Uani 1 1 d . . . H5A H 0.5432 0.3143 0.5730 0.026 Uiso 1 1 calc R . . H5B H 0.3563 0.3466 0.5236 0.026 Uiso 1 1 calc R . . C6 C 0.5459(3) 0.38757(15) 0.45822(16) 0.0241(5) Uani 1 1 d . . . H6A H 0.5824 0.4385 0.4960 0.029 Uiso 1 1 calc R . . H6B H 0.6478 0.3624 0.4404 0.029 Uiso 1 1 calc R . . C7 C 0.5029(3) 0.45600(16) 0.31494(17) 0.0287(5) Uani 1 1 d . . . H7A H 0.5969 0.4219 0.2992 0.034 Uiso 1 1 calc R . . H7B H 0.5520 0.5095 0.3435 0.034 Uiso 1 1 calc R . . C8 C 0.3729(3) 0.47516(15) 0.22910(17) 0.0283(5) Uani 1 1 d . . . H8A H 0.2741 0.5035 0.2470 0.034 Uiso 1 1 calc R . . H8B H 0.4237 0.5157 0.1914 0.034 Uiso 1 1 calc R . . C9 C 0.4271(3) 0.37723(15) 0.11824(17) 0.0272(5) Uani 1 1 d . . . H9A H 0.5427 0.3708 0.1571 0.033 Uiso 1 1 calc R . . H9B H 0.4326 0.4207 0.0709 0.033 Uiso 1 1 calc R . . C10 C 0.3704(3) 0.29520(15) 0.07293(15) 0.0238(5) Uani 1 1 d . . . H10A H 0.2555 0.3020 0.0334 0.029 Uiso 1 1 calc R . . H10B H 0.4502 0.2780 0.0333 0.029 Uiso 1 1 calc R . . N1 N 0.7935(2) 0.13766(12) 0.35784(12) 0.0218(4) Uani 1 1 d . . . N2 N 0.4691(2) 0.11967(12) 0.26082(12) 0.0195(4) Uani 1 1 d . . . N3 N 0.6958(2) 0.21871(12) 0.19638(12) 0.0206(4) Uani 1 1 d . . . O1 O 0.86964(18) 0.29750(10) 0.33691(11) 0.0224(3) Uani 1 1 d . . . O2 O 1.01928(18) 0.19136(9) 0.27002(10) 0.0207(3) Uani 1 1 d . . . O3 O 0.5533(2) 0.08560(10) 0.43479(10) 0.0216(3) Uani 1 1 d . . . O4 O 0.44051(19) 0.24865(9) 0.46027(10) 0.0219(3) Uani 1 1 d . . . O5 O 0.42431(19) 0.41043(10) 0.37828(11) 0.0249(4) Uani 1 1 d . . . O6 O 0.3116(2) 0.40329(10) 0.17318(11) 0.0280(4) Uani 1 1 d . . . O7 O 0.36497(18) 0.22974(9) 0.14162(10) 0.0199(3) Uani 1 1 d . . . P1 P 0.83414(7) 0.20776(3) 0.28892(4) 0.01710(13) Uani 1 1 d . . . P2 P 0.61662(7) 0.09037(3) 0.34242(4) 0.01707(13) Uani 1 1 d . . . P3 P 0.51931(7) 0.17098(4) 0.17893(4) 0.01704(14) Uani 1 1 d . . . Cl1 Cl 0.66114(7) -0.03362(3) 0.32217(4) 0.02684(14) Uani 1 1 d . . . Cl2 Cl 0.51700(8) 0.09036(4) 0.07203(4) 0.02765(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0157(10) 0.0249(12) 0.0251(11) -0.0019(9) 0.0027(9) -0.0059(9) C2 0.0171(10) 0.0238(12) 0.0224(11) 0.0014(9) 0.0038(8) -0.0036(9) C3 0.0215(11) 0.0205(11) 0.0223(11) 0.0014(9) 0.0074(9) -0.0018(9) C4 0.0215(11) 0.0230(12) 0.0226(11) 0.0017(9) 0.0079(9) 0.0000(9) C5 0.0217(11) 0.0220(12) 0.0206(10) -0.0025(9) 0.0028(9) 0.0030(9) C6 0.0210(11) 0.0213(11) 0.0284(12) -0.0013(9) 0.0014(9) 0.0022(9) C7 0.0274(12) 0.0254(13) 0.0343(13) 0.0049(10) 0.0084(10) -0.0062(10) C8 0.0341(13) 0.0191(12) 0.0330(13) 0.0023(10) 0.0100(10) 0.0012(10) C9 0.0266(12) 0.0257(12) 0.0309(12) 0.0048(10) 0.0092(10) -0.0021(10) C10 0.0248(11) 0.0283(12) 0.0184(10) 0.0074(9) 0.0045(9) 0.0016(10) N1 0.0208(9) 0.0237(10) 0.0189(9) 0.0039(7) -0.0005(7) -0.0033(8) N2 0.0168(9) 0.0238(10) 0.0177(9) 0.0031(7) 0.0034(7) -0.0045(7) N3 0.0166(9) 0.0244(10) 0.0201(9) 0.0064(7) 0.0024(7) -0.0035(7) O1 0.0168(7) 0.0200(8) 0.0311(8) -0.0055(6) 0.0066(6) -0.0028(6) O2 0.0156(7) 0.0187(8) 0.0281(8) -0.0022(6) 0.0051(6) 0.0006(6) O3 0.0247(8) 0.0247(8) 0.0163(7) 0.0038(6) 0.0064(6) 0.0065(6) O4 0.0294(8) 0.0172(8) 0.0194(7) 0.0007(6) 0.0053(6) -0.0004(6) O5 0.0203(8) 0.0258(9) 0.0284(8) 0.0064(7) 0.0047(7) 0.0009(6) O6 0.0260(8) 0.0256(9) 0.0333(9) 0.0017(7) 0.0083(7) 0.0000(7) O7 0.0163(7) 0.0227(8) 0.0206(7) 0.0055(6) 0.0036(6) 0.0011(6) P1 0.0147(3) 0.0172(3) 0.0189(3) 0.0000(2) 0.0023(2) -0.0005(2) P2 0.0189(3) 0.0171(3) 0.0155(3) 0.0014(2) 0.0040(2) -0.0005(2) P3 0.0159(3) 0.0202(3) 0.0149(2) 0.0016(2) 0.0029(2) -0.0014(2) Cl1 0.0339(3) 0.0187(3) 0.0302(3) -0.0004(2) 0.0120(2) 0.0028(2) Cl2 0.0327(3) 0.0295(3) 0.0214(3) -0.0061(2) 0.0070(2) -0.0010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.452(2) . ? C1 C2 1.505(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.463(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3 1.456(3) . ? C3 C4 1.497(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O4 1.413(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O4 1.424(3) . ? C5 C6 1.499(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O5 1.419(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O5 1.427(3) . ? C7 C8 1.502(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O6 1.432(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O6 1.412(3) . ? C9 C10 1.487(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O7 1.459(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N1 P2 1.5748(18) . ? N1 P1 1.5851(19) . ? N2 P2 1.5777(18) . ? N2 P3 1.5789(18) . ? N3 P3 1.5742(18) . ? N3 P1 1.5874(18) . ? O1 P1 1.5859(16) . ? O2 P1 1.5830(15) . ? O3 P2 1.5569(15) . ? O7 P3 1.5532(15) . ? P2 Cl1 2.0242(8) . ? P3 Cl2 2.0315(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.09(16) . . ? O1 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? O1 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? O2 C2 C1 104.15(16) . . ? O2 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? O2 C2 H2B 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? O3 C3 C4 107.84(17) . . ? O3 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? O3 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.5 . . ? O4 C4 C3 106.80(17) . . ? O4 C4 H4A 110.4 . . ? C3 C4 H4A 110.4 . . ? O4 C4 H4B 110.4 . . ? C3 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? O4 C5 C6 107.17(17) . . ? O4 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O4 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.5 . . ? O5 C6 C5 109.03(18) . . ? O5 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O5 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? O5 C7 C8 109.77(19) . . ? O5 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O5 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O6 C8 C7 115.3(2) . . ? O6 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? O6 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? O6 C9 C10 109.89(19) . . ? O6 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O6 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O7 C10 C9 110.57(18) . . ? O7 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O7 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? P2 N1 P1 122.25(11) . . ? P2 N2 P3 118.29(11) . . ? P3 N3 P1 122.24(11) . . ? C1 O1 P1 111.07(13) . . ? C2 O2 P1 110.24(13) . . ? C3 O3 P2 125.19(13) . . ? C4 O4 C5 114.09(16) . . ? C6 O5 C7 111.11(17) . . ? C9 O6 C8 112.28(18) . . ? C10 O7 P3 122.56(13) . . ? O2 P1 N1 108.76(9) . . ? O2 P1 O1 97.90(8) . . ? N1 P1 O1 112.10(9) . . ? O2 P1 N3 112.12(9) . . ? N1 P1 N3 115.85(9) . . ? O1 P1 N3 108.69(9) . . ? O3 P2 N1 109.81(9) . . ? O3 P2 N2 111.32(9) . . ? N1 P2 N2 118.76(10) . . ? O3 P2 Cl1 100.51(6) . . ? N1 P2 Cl1 107.50(8) . . ? N2 P2 Cl1 107.25(8) . . ? O7 P3 N3 113.14(9) . . ? O7 P3 N2 105.86(9) . . ? N3 P3 N2 118.62(9) . . ? O7 P3 Cl2 102.48(6) . . ? N3 P3 Cl2 107.10(8) . . ? N2 P3 Cl2 108.40(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -34.2(2) . . . . ? O3 C3 C4 O4 65.6(2) . . . . ? O4 C5 C6 O5 68.1(2) . . . . ? O5 C7 C8 O6 -68.8(3) . . . . ? O6 C9 C10 O7 -60.6(2) . . . . ? C2 C1 O1 P1 25.6(2) . . . . ? C1 C2 O2 P1 30.98(19) . . . . ? C4 C3 O3 P2 -116.40(17) . . . . ? C3 C4 O4 C5 -175.63(17) . . . . ? C6 C5 O4 C4 171.84(17) . . . . ? C5 C6 O5 C7 -167.96(18) . . . . ? C8 C7 O5 C6 176.98(19) . . . . ? C10 C9 O6 C8 171.30(18) . . . . ? C7 C8 O6 C9 -79.5(2) . . . . ? C9 C10 O7 P3 -91.7(2) . . . . ? C2 O2 P1 N1 -131.77(14) . . . . ? C2 O2 P1 O1 -15.14(15) . . . . ? C2 O2 P1 N3 98.79(15) . . . . ? P2 N1 P1 O2 -135.36(13) . . . . ? P2 N1 P1 O1 117.51(13) . . . . ? P2 N1 P1 N3 -8.02(18) . . . . ? C1 O1 P1 O2 -6.93(15) . . . . ? C1 O1 P1 N1 107.07(15) . . . . ? C1 O1 P1 N3 -123.56(14) . . . . ? P3 N3 P1 O2 132.66(13) . . . . ? P3 N3 P1 N1 7.01(18) . . . . ? P3 N3 P1 O1 -120.24(14) . . . . ? C3 O3 P2 N1 134.66(17) . . . . ? C3 O3 P2 N2 1.1(2) . . . . ? C3 O3 P2 Cl1 -112.27(16) . . . . ? P1 N1 P2 O3 -135.45(13) . . . . ? P1 N1 P2 N2 -5.78(19) . . . . ? P1 N1 P2 Cl1 116.07(12) . . . . ? P3 N2 P2 O3 149.84(11) . . . . ? P3 N2 P2 N1 20.85(18) . . . . ? P3 N2 P2 Cl1 -101.12(12) . . . . ? C10 O7 P3 N3 40.51(18) . . . . ? C10 O7 P3 N2 172.03(15) . . . . ? C10 O7 P3 Cl2 -74.45(16) . . . . ? P1 N3 P3 O7 132.63(13) . . . . ? P1 N3 P3 N2 7.76(19) . . . . ? P1 N3 P3 Cl2 -115.20(12) . . . . ? P2 N2 P3 O7 -150.15(12) . . . . ? P2 N2 P3 N3 -21.81(18) . . . . ? P2 N2 P3 Cl2 100.50(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.654 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.073 # Attachment '7a.cif' data_7a _database_code_depnum_ccdc_archive 'CCDC 270530' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H8 Cl3 N4 O2 P3' _chemical_formula_weight 331.39 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_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' _cell_length_a 6.7181(5) _cell_length_b 12.6485(12) _cell_length_c 13.7542(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1168.75(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 24153 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.180 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.6761 _exptl_absorpt_correction_T_max 0.9434 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 13470 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2678 _reflns_number_gt 2601 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0252P)^2^+0.7153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0048(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.40(7) _refine_ls_number_reflns 2678 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.010 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2493(4) 0.50874(17) 0.60049(16) 0.0245(5) Uani 1 1 d . . . H1A H 0.3131 0.5147 0.6643 0.037 Uiso 1 1 calc R . . H1B H 0.1350 0.5567 0.5975 0.037 Uiso 1 1 calc R . . H1C H 0.3451 0.5277 0.5496 0.037 Uiso 1 1 calc R . . C2 C 0.6932(3) 0.33626(17) 0.67995(16) 0.0197(4) Uani 1 1 d . . . H2A H 0.6553 0.3997 0.7178 0.024 Uiso 1 1 calc R . . H2B H 0.8162 0.3535 0.6436 0.024 Uiso 1 1 calc R . . C3 C 0.7384(4) 0.24755(18) 0.75010(16) 0.0220(5) Uani 1 1 d . . . H3A H 0.7384 0.1801 0.7136 0.026 Uiso 1 1 calc R . . H3B H 0.8742 0.2581 0.7763 0.026 Uiso 1 1 calc R . . N1 N 0.2856(3) 0.32431(13) 0.75291(12) 0.0142(3) Uani 1 1 d . . . N2 N 0.3268(3) 0.11286(14) 0.76373(13) 0.0190(4) Uani 1 1 d . . . N3 N 0.1932(3) 0.20463(14) 0.59639(13) 0.0184(4) Uani 1 1 d . . . N4 N 0.5346(3) 0.31348(15) 0.60983(14) 0.0195(4) Uani 1 1 d . . . O1 O 0.1822(2) 0.40051(12) 0.58568(11) 0.0207(3) Uani 1 1 d . . . O2 O 0.5997(2) 0.23775(12) 0.83220(11) 0.0185(3) Uani 1 1 d . . . P1 P 0.29938(8) 0.31030(4) 0.63758(4) 0.01467(12) Uani 1 1 d . . . P2 P 0.37115(8) 0.22618(4) 0.81001(4) 0.01475(12) Uani 1 1 d . . . P3 P 0.24143(8) 0.10141(4) 0.65720(4) 0.01509(12) Uani 1 1 d . . . Cl1 Cl 0.26557(9) 0.22793(5) 0.94479(4) 0.02599(13) Uani 1 1 d . . . Cl2 Cl 0.42829(9) 0.00659(4) 0.58476(4) 0.02607(14) Uani 1 1 d . . . Cl3 Cl -0.00083(8) 0.00923(4) 0.65937(4) 0.02245(13) Uani 1 1 d . . . H4N H 0.568(5) 0.305(2) 0.552(2) 0.032(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0361(13) 0.0122(9) 0.0253(10) 0.0019(8) -0.0063(10) -0.0034(9) C2 0.0155(10) 0.0200(10) 0.0237(11) -0.0004(8) 0.0020(9) -0.0027(8) C3 0.0166(11) 0.0243(11) 0.0252(11) 0.0019(9) 0.0032(9) 0.0018(9) N1 0.0146(8) 0.0136(8) 0.0146(8) -0.0009(6) -0.0001(7) -0.0003(7) N2 0.0245(10) 0.0139(8) 0.0185(9) 0.0021(7) -0.0041(7) -0.0013(7) N3 0.0238(10) 0.0154(8) 0.0160(8) 0.0012(6) -0.0044(7) -0.0029(7) N4 0.0217(10) 0.0224(9) 0.0143(9) -0.0018(7) 0.0047(7) -0.0029(8) O1 0.0246(8) 0.0140(7) 0.0236(8) 0.0024(6) -0.0079(7) -0.0010(6) O2 0.0172(7) 0.0197(7) 0.0186(7) -0.0002(6) -0.0034(6) -0.0001(6) P1 0.0173(3) 0.0122(2) 0.0145(2) 0.00031(18) -0.0021(2) -0.0003(2) P2 0.0170(3) 0.0142(2) 0.0131(2) 0.00021(19) -0.0002(2) -0.0004(2) P3 0.0178(3) 0.0119(2) 0.0156(2) 0.00000(18) -0.0007(2) -0.0018(2) Cl1 0.0321(3) 0.0311(3) 0.0148(2) 0.0007(2) 0.0046(2) -0.0038(2) Cl2 0.0300(3) 0.0206(2) 0.0276(3) -0.0019(2) 0.0107(2) 0.0025(2) Cl3 0.0202(2) 0.0185(2) 0.0287(3) -0.0012(2) -0.0007(2) -0.0056(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.456(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N4 1.466(3) . ? C2 C3 1.511(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O2 1.469(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N1 P2 1.5772(18) . ? N1 P1 1.5987(17) . ? N2 P3 1.5800(19) . ? N2 P2 1.5964(19) . ? N3 P3 1.5840(18) . ? N3 P1 1.6175(18) . ? N4 P1 1.626(2) . ? N4 H4N 0.83(3) . ? O1 P1 1.5594(16) . ? O2 P2 1.5720(16) . ? P1 P2 2.6437(8) . ? P1 P3 2.6842(8) . ? P2 Cl1 1.9849(8) . ? P3 Cl2 2.0018(8) . ? P3 Cl3 2.0024(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C2 C3 114.86(18) . . ? N4 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? N4 C2 H2B 108.5 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? O2 C3 C2 115.21(18) . . ? O2 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? O2 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? P2 N1 P1 112.70(10) . . ? P3 N2 P2 121.32(12) . . ? P3 N3 P1 113.94(11) . . ? C2 N4 P1 123.84(16) . . ? C2 N4 H4N 117(2) . . ? P1 N4 H4N 119(2) . . ? C1 O1 P1 117.88(14) . . ? C3 O2 P2 118.56(14) . . ? O1 P1 N1 110.12(9) . . ? O1 P1 N3 102.80(9) . . ? N1 P1 N3 114.44(9) . . ? O1 P1 N4 111.41(10) . . ? N1 P1 N4 106.63(10) . . ? N3 P1 N4 111.52(10) . . ? O1 P1 P2 142.87(7) . . ? N1 P1 P2 33.39(6) . . ? N3 P1 P2 93.56(7) . . ? N4 P1 P2 92.48(7) . . ? O1 P1 P3 133.87(6) . . ? N1 P1 P3 90.06(7) . . ? N3 P1 P3 32.64(6) . . ? N4 P1 P3 100.89(7) . . ? P2 P1 P3 62.62(2) . . ? O2 P2 N1 112.28(9) . . ? O2 P2 N2 110.09(10) . . ? N1 P2 N2 116.10(9) . . ? O2 P2 Cl1 99.59(6) . . ? N1 P2 Cl1 109.04(7) . . ? N2 P2 Cl1 108.40(8) . . ? O2 P2 P1 108.35(6) . . ? N1 P2 P1 33.91(6) . . ? N2 P2 P1 88.25(7) . . ? Cl1 P2 P1 140.19(3) . . ? N2 P3 N3 119.23(10) . . ? N2 P3 Cl2 106.80(8) . . ? N3 P3 Cl2 111.06(8) . . ? N2 P3 Cl3 109.54(8) . . ? N3 P3 Cl3 108.76(8) . . ? Cl2 P3 Cl3 99.69(3) . . ? N2 P3 P1 87.16(7) . . ? N3 P3 P1 33.42(7) . . ? Cl2 P3 P1 116.66(3) . . ? Cl3 P3 P1 133.83(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.324 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.076 # Attachment '7c.cif' data_7c _database_code_depnum_ccdc_archive 'CCDC 624590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 Cl3 N3 O3 P3' _chemical_formula_weight 332.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_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 15.8813(10) _cell_length_b 5.9401(4) _cell_length_c 24.6234(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.246(3) _cell_angle_gamma 90.00 _cell_volume 2321.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1909 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7964 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 12237 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2630 _reflns_number_gt 2276 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0962P)^2^+14.7173P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2630 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1834 _refine_ls_wR_factor_gt 0.1740 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8875(3) 0.3315(9) 0.2665(2) 0.0286(11) Uani 1 1 d . . . H1A H 0.8663 0.1989 0.2459 0.034 Uiso 1 1 calc R . . H1B H 0.9109 0.4382 0.2402 0.034 Uiso 1 1 calc R . . C2 C 0.8138(3) 0.4439(9) 0.2934(2) 0.0303(11) Uani 1 1 d . . . H2A H 0.8360 0.5301 0.3252 0.036 Uiso 1 1 calc R . . H2B H 0.7878 0.5531 0.2674 0.036 Uiso 1 1 calc R . . C3 C 0.6777(4) -0.1813(11) 0.4018(2) 0.0370(13) Uani 1 1 d . . . H3A H 0.7063 -0.3224 0.3932 0.056 Uiso 1 1 calc R . . H3B H 0.6173 -0.2099 0.4051 0.056 Uiso 1 1 calc R . . H3C H 0.7013 -0.1211 0.4361 0.056 Uiso 1 1 calc R . . N1 N 0.9613(3) 0.1686(7) 0.40693(16) 0.0257(9) Uani 1 1 d . . . N2 N 0.8488(3) -0.0365(6) 0.33731(15) 0.0212(8) Uani 1 1 d . . . N3 N 0.7931(3) 0.2423(7) 0.41422(16) 0.0231(8) Uani 1 1 d . . . O1 O 0.9556(2) 0.2585(6) 0.30444(14) 0.0306(8) Uani 1 1 d . . . O2 O 0.7477(2) 0.2924(6) 0.31150(13) 0.0258(7) Uani 1 1 d . . . O3 O 0.6898(2) -0.0181(6) 0.35822(14) 0.0297(8) Uani 1 1 d . . . P1 P 0.88469(8) 0.2648(2) 0.43941(5) 0.0204(3) Uani 1 1 d . . . P2 P 0.93925(8) 0.0706(2) 0.34785(5) 0.0217(3) Uani 1 1 d . . . P3 P 0.77354(8) 0.1163(2) 0.35755(5) 0.0213(3) Uani 1 1 d . . . Cl1 Cl 0.90598(9) 0.5915(2) 0.45540(5) 0.0304(3) Uani 1 1 d . . . Cl2 Cl 0.89057(8) 0.1355(2) 0.51422(5) 0.0282(3) Uani 1 1 d . . . Cl3 Cl 1.02736(9) -0.1580(2) 0.33369(6) 0.0361(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.031(3) 0.034(3) 0.021(2) 0.003(2) -0.0024(19) 0.000(2) C2 0.038(3) 0.021(2) 0.032(3) 0.004(2) 0.003(2) 0.000(2) C3 0.035(3) 0.035(3) 0.041(3) -0.002(2) 0.010(2) -0.010(2) N1 0.024(2) 0.029(2) 0.024(2) -0.0041(17) -0.0022(16) -0.0012(17) N2 0.030(2) 0.0141(18) 0.0199(18) -0.0025(15) 0.0004(15) 0.0009(16) N3 0.023(2) 0.027(2) 0.0186(18) -0.0053(16) 0.0012(15) -0.0002(16) O1 0.0318(19) 0.034(2) 0.0263(18) 0.0088(15) -0.0008(14) -0.0052(16) O2 0.0265(17) 0.0272(18) 0.0234(17) -0.0008(14) -0.0037(13) 0.0009(14) O3 0.0243(17) 0.034(2) 0.0306(18) 0.0009(16) -0.0026(14) -0.0077(15) P1 0.0241(6) 0.0199(6) 0.0171(6) -0.0002(4) 0.0004(4) -0.0012(5) P2 0.0240(6) 0.0227(6) 0.0185(6) -0.0002(5) 0.0032(4) 0.0026(5) P3 0.0237(6) 0.0212(6) 0.0191(6) -0.0017(4) -0.0003(4) -0.0015(5) Cl1 0.0416(7) 0.0200(6) 0.0292(6) -0.0007(5) -0.0050(5) -0.0033(5) Cl2 0.0395(7) 0.0272(6) 0.0179(5) 0.0035(4) 0.0012(4) -0.0005(5) Cl3 0.0340(7) 0.0371(8) 0.0375(7) -0.0046(6) 0.0056(5) 0.0121(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.466(6) . ? C1 C2 1.521(7) . ? C2 O2 1.465(6) . ? C3 O3 1.464(7) . ? N1 P1 1.589(4) . ? N1 P2 1.593(4) . ? N2 P2 1.583(4) . ? N2 P3 1.596(4) . ? N3 P1 1.564(4) . ? N3 P3 1.603(4) . ? O1 P2 1.574(4) . ? O2 P3 1.585(4) . ? O3 P3 1.552(4) . ? P1 Cl2 1.9947(16) . ? P1 Cl1 2.0065(17) . ? P2 Cl3 1.9902(18) . ? P2 P3 2.6657(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 114.5(4) . . ? O2 C2 C1 115.8(4) . . ? P1 N1 P2 116.4(2) . . ? P2 N2 P3 114.0(2) . . ? P1 N3 P3 122.0(3) . . ? C1 O1 P2 120.3(3) . . ? C2 O2 P3 117.0(3) . . ? C3 O3 P3 119.1(3) . . ? N3 P1 N1 119.3(2) . . ? N3 P1 Cl2 110.02(17) . . ? N1 P1 Cl2 108.51(17) . . ? N3 P1 Cl1 107.89(17) . . ? N1 P1 Cl1 108.66(17) . . ? Cl2 P1 Cl1 100.94(7) . . ? O1 P2 N2 110.3(2) . . ? O1 P2 N1 108.9(2) . . ? N2 P2 N1 117.5(2) . . ? O1 P2 Cl3 103.23(16) . . ? N2 P2 Cl3 109.69(16) . . ? N1 P2 Cl3 106.15(17) . . ? O1 P2 P3 100.28(15) . . ? N2 P2 P3 33.16(14) . . ? N1 P2 P3 93.66(16) . . ? Cl3 P2 P3 142.05(8) . . ? O3 P3 O2 98.59(19) . . ? O3 P3 N2 111.3(2) . . ? O2 P3 N2 109.1(2) . . ? O3 P3 N3 111.6(2) . . ? O2 P3 N3 110.5(2) . . ? N2 P3 N3 114.5(2) . . ? O3 P3 P2 142.95(16) . . ? O2 P3 P2 103.40(14) . . ? N2 P3 P2 32.87(14) . . ? N3 P3 P2 88.11(15) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.788 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.168 # Attachment '8a.cif' data_8a _database_code_depnum_ccdc_archive 'CCDC 624591' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cl3 N4 O2 P3' _chemical_formula_weight 393.46 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.2569(12) _cell_length_b 11.0110(8) _cell_length_c 7.9969(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.470(6) _cell_angle_gamma 90.00 _cell_volume 1509.86(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3570 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8360 _exptl_absorpt_correction_T_max 0.9638 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 22583 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3453 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+28.1046P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3453 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.2347 _refine_ls_wR_factor_gt 0.2306 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5196(5) 0.1736(9) 0.8871(12) 0.036(2) Uani 1 1 d . . . H1A H 0.5254 0.1434 1.0045 0.043 Uiso 1 1 calc R . . H1B H 0.5524 0.2468 0.8805 0.043 Uiso 1 1 calc R . . C2 C 0.5409(5) 0.0774(10) 0.7682(12) 0.039(2) Uani 1 1 d . . . H2A H 0.5628 0.1150 0.6713 0.047 Uiso 1 1 calc R . . H2B H 0.5807 0.0223 0.8260 0.047 Uiso 1 1 calc R . . C3 C 0.1226(5) -0.0753(7) 0.8671(10) 0.0242(16) Uani 1 1 d . . . C4 C 0.1015(5) -0.1796(8) 0.9451(11) 0.0312(18) Uani 1 1 d . . . H4 H 0.1397 -0.2285 1.0080 0.037 Uiso 1 1 calc R . . C5 C 0.0231(5) -0.2120(9) 0.9299(11) 0.036(2) Uani 1 1 d . . . H5 H 0.0071 -0.2839 0.9819 0.043 Uiso 1 1 calc R . . C6 C -0.0316(5) -0.1385(10) 0.8383(12) 0.038(2) Uani 1 1 d . . . H6 H -0.0852 -0.1603 0.8284 0.046 Uiso 1 1 calc R . . C7 C -0.0091(5) -0.0343(9) 0.7614(12) 0.036(2) Uani 1 1 d . . . H7 H -0.0469 0.0149 0.6981 0.043 Uiso 1 1 calc R . . C8 C 0.0697(5) -0.0010(8) 0.7766(11) 0.0300(18) Uani 1 1 d . . . H8 H 0.0860 0.0711 0.7256 0.036 Uiso 1 1 calc R . . N1 N 0.3390(4) 0.0084(6) 0.8408(8) 0.0270(14) Uani 1 1 d . . . N2 N 0.2228(4) -0.0123(7) 0.5809(8) 0.0276(15) Uani 1 1 d . . . N3 N 0.3514(4) 0.1256(7) 0.5505(9) 0.0279(15) Uani 1 1 d . . . N4 N 0.4380(4) 0.2001(7) 0.8294(10) 0.0323(16) Uani 1 1 d . . . H4A H 0.4154 0.2700 0.8455 0.039 Uiso 1 1 calc R . . O1 O 0.4704(3) 0.0097(6) 0.7105(8) 0.0331(14) Uani 1 1 d . . . O2 O 0.2013(3) -0.0388(5) 0.8952(6) 0.0231(11) Uani 1 1 d . . . P1 P 0.39372(11) 0.08563(18) 0.7319(2) 0.0210(4) Uani 1 1 d . . . P2 P 0.26141(11) -0.05276(18) 0.7622(2) 0.0206(4) Uani 1 1 d . . . P3 P 0.26625(11) 0.08703(18) 0.4838(2) 0.0201(4) Uani 1 1 d . . . Cl1 Cl 0.27616(13) -0.23509(18) 0.7544(3) 0.0329(5) Uani 1 1 d . . . Cl2 Cl 0.26252(12) 0.03752(19) 0.2446(2) 0.0290(5) Uani 1 1 d . . . Cl3 Cl 0.19889(12) 0.23707(18) 0.4576(3) 0.0319(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(4) 0.047(5) 0.039(5) 0.002(4) -0.007(3) -0.001(4) C2 0.015(4) 0.058(6) 0.042(5) 0.003(4) 0.001(3) 0.005(4) C3 0.027(4) 0.024(4) 0.023(4) -0.008(3) 0.005(3) -0.002(3) C4 0.033(4) 0.035(5) 0.027(4) 0.005(3) 0.006(3) -0.003(4) C5 0.037(5) 0.043(5) 0.031(5) -0.002(4) 0.014(4) -0.014(4) C6 0.027(4) 0.055(6) 0.032(5) -0.010(4) 0.006(3) -0.012(4) C7 0.023(4) 0.048(5) 0.037(5) -0.006(4) 0.003(3) 0.004(4) C8 0.030(4) 0.025(4) 0.035(5) 0.000(3) 0.006(3) -0.001(3) N1 0.028(3) 0.031(4) 0.022(3) 0.004(3) -0.001(3) -0.006(3) N2 0.023(3) 0.038(4) 0.020(3) 0.009(3) -0.005(2) -0.007(3) N3 0.023(3) 0.031(4) 0.029(4) 0.006(3) 0.001(3) -0.006(3) N4 0.022(3) 0.029(4) 0.044(4) -0.012(3) -0.003(3) -0.002(3) O1 0.023(3) 0.035(3) 0.041(3) -0.003(3) 0.004(2) 0.008(2) O2 0.020(2) 0.030(3) 0.019(3) -0.005(2) 0.0007(19) -0.005(2) P1 0.0173(9) 0.0231(10) 0.0221(9) -0.0011(7) 0.0005(7) 0.0010(7) P2 0.0201(9) 0.0252(10) 0.0161(9) 0.0010(7) -0.0001(7) -0.0027(7) P3 0.0225(9) 0.0217(9) 0.0155(8) 0.0004(7) -0.0006(7) 0.0016(7) Cl1 0.0354(11) 0.0250(10) 0.0384(12) 0.0013(8) 0.0041(9) 0.0021(8) Cl2 0.0370(11) 0.0322(10) 0.0179(9) -0.0002(7) 0.0029(7) 0.0088(8) Cl3 0.0345(11) 0.0266(10) 0.0322(11) -0.0055(8) -0.0066(8) 0.0112(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.460(10) . ? C1 C2 1.497(14) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.457(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.370(12) . ? C3 C4 1.375(11) . ? C3 O2 1.410(9) . ? C4 C5 1.392(12) . ? C4 H4 0.9500 . ? C5 C6 1.388(14) . ? C5 H5 0.9500 . ? C6 C7 1.378(14) . ? C6 H6 0.9500 . ? C7 C8 1.399(12) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? N1 P2 1.566(7) . ? N1 P1 1.600(7) . ? N2 P3 1.578(7) . ? N2 P2 1.589(6) . ? N3 P3 1.564(7) . ? N3 P1 1.611(7) . ? N4 P1 1.626(7) . ? N4 H4A 0.8800 . ? O1 P1 1.590(6) . ? O2 P2 1.575(5) . ? P2 Cl1 2.026(3) . ? P3 Cl2 1.983(3) . ? P3 Cl3 2.017(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 C2 103.8(7) . . ? N4 C1 H1A 111.0 . . ? C2 C1 H1A 111.0 . . ? N4 C1 H1B 111.0 . . ? C2 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? O1 C2 C1 107.8(7) . . ? O1 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? O1 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.5 . . ? C8 C3 C4 122.9(8) . . ? C8 C3 O2 119.1(7) . . ? C4 C3 O2 117.7(7) . . ? C3 C4 C5 118.6(8) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 119.6(9) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 120.7(8) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.0(9) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 118.2(8) . . ? C3 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? P2 N1 P1 122.7(4) . . ? P3 N2 P2 118.0(4) . . ? P3 N3 P1 123.1(4) . . ? C1 N4 P1 112.4(6) . . ? C1 N4 H4A 123.8 . . ? P1 N4 H4A 123.8 . . ? C2 O1 P1 111.9(5) . . ? C3 O2 P2 124.1(5) . . ? O1 P1 N1 109.2(4) . . ? O1 P1 N3 110.2(4) . . ? N1 P1 N3 113.6(4) . . ? O1 P1 N4 96.2(4) . . ? N1 P1 N4 115.2(4) . . ? N3 P1 N4 111.1(4) . . ? N1 P2 O2 106.6(3) . . ? N1 P2 N2 119.8(4) . . ? O2 P2 N2 110.4(3) . . ? N1 P2 Cl1 109.5(3) . . ? O2 P2 Cl1 102.3(2) . . ? N2 P2 Cl1 106.9(3) . . ? N3 P3 N2 120.0(4) . . ? N3 P3 Cl2 109.3(3) . . ? N2 P3 Cl2 108.5(3) . . ? N3 P3 Cl3 108.7(3) . . ? N2 P3 Cl3 108.6(3) . . ? Cl2 P3 Cl3 99.73(11) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.594 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.180 # Attachment '8c.cif' data_8c _database_code_depnum_ccdc_archive 'CCDC 624592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 Cl3 N3 O3 P3' _chemical_formula_weight 332.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7423(4) _cell_length_b 8.0657(5) _cell_length_c 17.2362(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.165(4) _cell_angle_gamma 90.00 _cell_volume 1208.34(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2825 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5983 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 2687 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2687 _reflns_number_gt 2284 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+17.0464P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2687 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0983 _refine_ls_wR_factor_ref 0.2653 _refine_ls_wR_factor_gt 0.2467 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2132(14) 0.4908(14) -0.0817(6) 0.027(2) Uani 1 1 d . . . H1A H 0.2742 0.4665 -0.1255 0.033 Uiso 1 1 calc R . . H1B H 0.1025 0.4894 -0.1013 0.033 Uiso 1 1 calc R . . C2 C 0.2482(14) 0.3653(15) -0.0155(6) 0.029(2) Uani 1 1 d . . . H2A H 0.1823 0.2658 -0.0242 0.035 Uiso 1 1 calc R . . H2B H 0.3575 0.3307 -0.0112 0.035 Uiso 1 1 calc R . . C3 C 0.6089(18) 0.8481(17) 0.2852(8) 0.045(3) Uani 1 1 d . . . H3A H 0.7025 0.9078 0.2753 0.068 Uiso 1 1 calc R . . H3B H 0.6322 0.7724 0.3293 0.068 Uiso 1 1 calc R . . H3C H 0.5304 0.9278 0.2974 0.068 Uiso 1 1 calc R . . N1 N 0.4150(10) 0.6946(11) 0.0871(5) 0.0255(19) Uani 1 1 d . . . N2 N 0.2992(11) 0.9221(12) 0.1782(5) 0.026(2) Uani 1 1 d . . . N3 N 0.1133(10) 0.7476(12) 0.0731(5) 0.0247(19) Uani 1 1 d . . . O1 O 0.2573(9) 0.6512(9) -0.0460(4) 0.0251(16) Uani 1 1 d . . . O2 O 0.2140(9) 0.4547(9) 0.0549(4) 0.0237(16) Uani 1 1 d . . . O3 O 0.5548(10) 0.7584(11) 0.2195(5) 0.038(2) Uani 1 1 d . . . P1 P 0.2523(3) 0.6461(3) 0.04590(15) 0.0205(6) Uani 1 1 d . . . P2 P 0.4462(3) 0.8350(3) 0.14957(15) 0.0219(6) Uani 1 1 d . . . P3 P 0.1344(3) 0.8801(3) 0.14035(14) 0.0202(6) Uani 1 1 d . . . Cl1 Cl 0.5759(4) 1.0133(4) 0.10860(17) 0.0386(8) Uani 1 1 d . . . Cl2 Cl 0.0262(3) 1.0869(3) 0.10283(14) 0.0290(6) Uani 1 1 d . . . Cl3 Cl 0.0085(4) 0.8102(4) 0.22503(16) 0.0393(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(6) 0.020(5) 0.027(5) -0.004(4) 0.010(5) -0.007(5) C2 0.026(6) 0.025(6) 0.037(6) -0.006(5) 0.006(5) -0.005(5) C3 0.058(9) 0.032(7) 0.045(7) 0.005(6) -0.003(6) 0.020(7) N1 0.021(5) 0.021(5) 0.033(5) -0.007(4) -0.001(4) -0.003(4) N2 0.029(5) 0.020(5) 0.028(4) -0.010(4) -0.001(4) -0.005(4) N3 0.018(4) 0.027(5) 0.028(4) -0.014(4) -0.003(3) -0.003(4) O1 0.031(4) 0.022(4) 0.022(3) 0.002(3) 0.005(3) -0.001(3) O2 0.034(4) 0.014(3) 0.025(3) -0.003(3) 0.009(3) -0.001(3) O3 0.029(4) 0.026(4) 0.056(5) 0.005(4) -0.012(4) 0.002(4) P1 0.0217(13) 0.0180(13) 0.0216(11) -0.0002(10) 0.0018(10) -0.0028(11) P2 0.0206(13) 0.0186(13) 0.0255(12) -0.0029(11) -0.0026(9) -0.0014(11) P3 0.0230(13) 0.0190(13) 0.0183(11) -0.0004(10) 0.0003(9) -0.0013(10) Cl1 0.0421(17) 0.0332(16) 0.0414(15) -0.0015(13) 0.0082(13) -0.0120(13) Cl2 0.0376(15) 0.0235(13) 0.0253(11) -0.0005(10) 0.0001(10) 0.0083(12) Cl3 0.0477(18) 0.0437(18) 0.0290(13) 0.0038(13) 0.0154(12) -0.0101(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.466(13) . ? C1 C2 1.531(16) . ? C2 O2 1.470(12) . ? C3 O3 1.383(16) . ? N1 P2 1.567(9) . ? N1 P1 1.570(9) . ? N2 P3 1.554(9) . ? N2 P2 1.589(10) . ? N3 P3 1.573(9) . ? N3 P1 1.577(9) . ? O1 P1 1.589(7) . ? O2 P1 1.591(7) . ? O3 P2 1.578(9) . ? P2 Cl1 2.007(4) . ? P3 Cl2 1.991(4) . ? P3 Cl3 2.001(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 104.3(8) . . ? O2 C2 C1 104.4(9) . . ? P2 N1 P1 124.9(6) . . ? P3 N2 P2 121.2(5) . . ? P3 N3 P1 122.6(6) . . ? C1 O1 P1 111.2(6) . . ? C2 O2 P1 109.4(6) . . ? C3 O3 P2 123.0(8) . . ? N1 P1 N3 115.2(5) . . ? N1 P1 O1 108.9(5) . . ? N3 P1 O1 112.8(5) . . ? N1 P1 O2 112.8(5) . . ? N3 P1 O2 107.3(5) . . ? O1 P1 O2 98.7(4) . . ? N1 P2 O3 106.7(5) . . ? N1 P2 N2 116.5(5) . . ? O3 P2 N2 112.1(5) . . ? N1 P2 Cl1 109.8(4) . . ? O3 P2 Cl1 103.5(4) . . ? N2 P2 Cl1 107.4(4) . . ? N2 P3 N3 119.2(5) . . ? N2 P3 Cl2 109.9(4) . . ? N3 P3 Cl2 108.4(4) . . ? N2 P3 Cl3 108.2(4) . . ? N3 P3 Cl3 108.4(4) . . ? Cl2 P3 Cl3 101.18(18) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 1.415 _refine_diff_density_min -0.771 _refine_diff_density_rms 0.220 # Attachment '8e.cif' data_8e _database_code_depnum_ccdc_archive 'CCDC 624593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H9 Cl3 N3 O3 P3' _chemical_formula_weight 394.44 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5409(2) _cell_length_b 17.1394(3) _cell_length_c 10.6213(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.5880(10) _cell_angle_gamma 90.00 _cell_volume 1464.83(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3448 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.789 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8311 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 19576 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3352 _reflns_number_gt 2830 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.9335P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3352 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6275(3) 0.51694(11) 0.1951(2) 0.0264(4) Uani 1 1 d . . . H1A H 0.5680 0.5332 0.2563 0.032 Uiso 1 1 calc R . . H1B H 0.6125 0.5576 0.1258 0.032 Uiso 1 1 calc R . . C2 C 0.8111(3) 0.50363(11) 0.2715(2) 0.0245(4) Uani 1 1 d . . . H2A H 0.8782 0.5102 0.2123 0.029 Uiso 1 1 calc R . . H2B H 0.8518 0.5404 0.3474 0.029 Uiso 1 1 calc R . . C3 C 0.3511(2) 0.12564(11) 0.25814(19) 0.0180(4) Uani 1 1 d . . . C4 C 0.3513(2) 0.08295(12) 0.3687(2) 0.0227(4) Uani 1 1 d . . . H4 H 0.3877 0.1056 0.4553 0.027 Uiso 1 1 calc R . . C5 C 0.2967(3) 0.00601(12) 0.3495(2) 0.0274(5) Uani 1 1 d . . . H5 H 0.2971 -0.0247 0.4241 0.033 Uiso 1 1 calc R . . C6 C 0.2418(3) -0.02639(12) 0.2225(2) 0.0284(5) Uani 1 1 d . . . H6 H 0.2049 -0.0790 0.2103 0.034 Uiso 1 1 calc R . . C7 C 0.2408(3) 0.01831(13) 0.1133(2) 0.0270(5) Uani 1 1 d . . . H7 H 0.2023 -0.0038 0.0263 0.032 Uiso 1 1 calc R . . C8 C 0.2959(2) 0.09535(12) 0.1303(2) 0.0229(4) Uani 1 1 d . . . H8 H 0.2956 0.1262 0.0559 0.028 Uiso 1 1 calc R . . N1 N 0.5859(2) 0.32253(9) 0.29424(17) 0.0205(4) Uani 1 1 d . . . N2 N 0.6464(2) 0.18716(9) 0.18479(17) 0.0218(4) Uani 1 1 d . . . N3 N 0.7522(2) 0.32519(9) 0.11866(17) 0.0222(4) Uani 1 1 d . . . O1 O 0.56670(17) 0.44158(8) 0.13415(14) 0.0226(3) Uani 1 1 d . . . O2 O 0.81898(17) 0.42379(8) 0.31875(14) 0.0226(3) Uani 1 1 d . . . O3 O 0.40051(16) 0.20491(7) 0.27631(14) 0.0190(3) Uani 1 1 d . . . P1 P 0.67921(6) 0.37266(3) 0.21552(5) 0.01730(12) Uani 1 1 d . . . P2 P 0.58315(6) 0.23085(3) 0.29038(5) 0.01733(12) Uani 1 1 d . . . P3 P 0.72405(6) 0.23527(3) 0.09329(5) 0.01704(12) Uani 1 1 d . . . Cl1 Cl 0.71845(6) 0.18916(3) 0.47261(5) 0.02415(13) Uani 1 1 d . . . Cl2 Cl 0.93807(6) 0.18506(3) 0.10013(5) 0.02508(13) Uani 1 1 d . . . Cl3 Cl 0.59013(7) 0.21608(3) -0.09806(5) 0.03078(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0305(11) 0.0139(9) 0.0332(12) 0.0017(8) 0.0086(9) -0.0011(8) C2 0.0275(11) 0.0132(9) 0.0329(12) 0.0012(8) 0.0102(9) -0.0037(8) C3 0.0148(9) 0.0167(9) 0.0239(10) 0.0004(7) 0.0084(8) 0.0007(7) C4 0.0238(10) 0.0239(10) 0.0230(10) -0.0019(8) 0.0114(8) -0.0027(8) C5 0.0282(11) 0.0247(11) 0.0335(12) 0.0048(9) 0.0159(10) -0.0033(8) C6 0.0268(11) 0.0215(10) 0.0401(13) -0.0047(9) 0.0154(10) -0.0059(8) C7 0.0231(10) 0.0304(11) 0.0278(11) -0.0096(9) 0.0086(9) -0.0048(8) C8 0.0204(10) 0.0278(11) 0.0214(10) 0.0019(8) 0.0080(8) 0.0009(8) N1 0.0291(9) 0.0143(8) 0.0236(9) 0.0000(6) 0.0161(7) 0.0011(6) N2 0.0292(9) 0.0137(8) 0.0289(9) -0.0022(6) 0.0183(8) -0.0017(6) N3 0.0289(9) 0.0181(8) 0.0244(9) 0.0002(7) 0.0155(8) -0.0035(7) O1 0.0265(7) 0.0151(7) 0.0233(7) 0.0015(5) 0.0045(6) -0.0002(5) O2 0.0263(7) 0.0154(7) 0.0229(7) 0.0014(5) 0.0037(6) -0.0005(5) O3 0.0188(7) 0.0158(6) 0.0252(7) -0.0007(5) 0.0109(6) 0.0011(5) P1 0.0217(3) 0.0125(2) 0.0184(3) 0.00101(17) 0.0076(2) -0.00080(18) P2 0.0214(3) 0.0131(2) 0.0207(3) 0.00043(18) 0.0112(2) -0.00003(18) P3 0.0183(2) 0.0164(2) 0.0181(2) -0.00140(18) 0.00847(19) -0.00093(18) Cl1 0.0253(2) 0.0223(2) 0.0240(3) 0.00486(18) 0.0070(2) -0.00065(18) Cl2 0.0207(2) 0.0270(3) 0.0302(3) 0.0003(2) 0.0120(2) 0.00351(18) Cl3 0.0268(3) 0.0410(3) 0.0214(3) -0.0073(2) 0.0039(2) -0.0006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.460(2) . ? C1 C2 1.522(3) . ? C2 O2 1.451(2) . ? C3 C8 1.380(3) . ? C3 C4 1.383(3) . ? C3 O3 1.417(2) . ? C4 C5 1.391(3) . ? C5 C6 1.387(3) . ? C6 C7 1.387(3) . ? C7 C8 1.393(3) . ? N1 P2 1.5718(16) . ? N1 P1 1.5871(16) . ? N2 P3 1.5802(16) . ? N2 P2 1.5861(16) . ? N3 P3 1.5692(17) . ? N3 P1 1.5935(17) . ? O1 P1 1.5839(14) . ? O2 P1 1.5867(14) . ? O3 P2 1.5802(13) . ? P2 Cl1 2.0230(7) . ? P3 Cl3 1.9971(7) . ? P3 Cl2 1.9995(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 104.69(15) . . ? O2 C2 C1 104.24(15) . . ? C8 C3 C4 122.61(18) . . ? C8 C3 O3 118.84(17) . . ? C4 C3 O3 118.45(17) . . ? C3 C4 C5 118.19(19) . . ? C6 C5 C4 120.6(2) . . ? C5 C6 C7 119.80(19) . . ? C6 C7 C8 120.5(2) . . ? C3 C8 C7 118.23(19) . . ? P2 N1 P1 122.23(10) . . ? P3 N2 P2 120.08(10) . . ? P3 N3 P1 122.80(10) . . ? C1 O1 P1 110.94(12) . . ? C2 O2 P1 110.17(12) . . ? C3 O3 P2 121.49(11) . . ? O1 P1 O2 98.25(7) . . ? O1 P1 N1 111.79(8) . . ? O2 P1 N1 109.22(8) . . ? O1 P1 N3 109.01(8) . . ? O2 P1 N3 111.19(8) . . ? N1 P1 N3 115.97(9) . . ? N1 P2 O3 106.82(8) . . ? N1 P2 N2 118.99(9) . . ? O3 P2 N2 111.07(8) . . ? N1 P2 Cl1 109.23(7) . . ? O3 P2 Cl1 102.72(6) . . ? N2 P2 Cl1 106.81(7) . . ? N3 P3 N2 118.60(9) . . ? N3 P3 Cl3 109.82(7) . . ? N2 P3 Cl3 108.94(7) . . ? N3 P3 Cl2 109.32(7) . . ? N2 P3 Cl2 108.69(7) . . ? Cl3 P3 Cl2 99.84(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.357 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.078 # Attachment '8f.cif' data_8f _database_code_depnum_ccdc_archive 'CCDC 624594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 Cl3 N4 O2 P3' _chemical_formula_weight 371.46 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6475(2) _cell_length_b 8.1876(2) _cell_length_c 17.5451(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.544(2) _cell_angle_gamma 90.00 _cell_volume 1370.50(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3129 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6303 _exptl_absorpt_correction_T_max 0.8225 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 12031 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3115 _reflns_number_gt 2796 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+1.0943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3115 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.20628(19) 0.7147(2) -0.00272(11) 0.0198(4) Uani 1 1 d . . . H1A H -0.1832 0.6437 -0.0448 0.024 Uiso 1 1 calc R . . H1B H -0.3023 0.7582 -0.0174 0.024 Uiso 1 1 calc R . . C2 C -0.19462(18) 0.6212(2) 0.07206(10) 0.0168(4) Uani 1 1 d . . . H2A H -0.2558 0.6698 0.1066 0.020 Uiso 1 1 calc R . . H2B H -0.2215 0.5055 0.0625 0.020 Uiso 1 1 calc R . . C3 C 0.10666(18) 1.2705(2) 0.20486(11) 0.0172(4) Uani 1 1 d . . . H3A H 0.0724 1.2217 0.2502 0.021 Uiso 1 1 calc R . . H3B H 0.0279 1.2786 0.1619 0.021 Uiso 1 1 calc R . . C4 C 0.1744(2) 1.4371(2) 0.22427(12) 0.0212(4) Uani 1 1 d . . . H4A H 0.1729 1.5045 0.1773 0.025 Uiso 1 1 calc R . . H4B H 0.1258 1.4968 0.2616 0.025 Uiso 1 1 calc R . . C5 C 0.3238(2) 1.3953(2) 0.25927(11) 0.0202(4) Uani 1 1 d . . . H5A H 0.3288 1.3632 0.3140 0.024 Uiso 1 1 calc R . . H5B H 0.3873 1.4890 0.2557 0.024 Uiso 1 1 calc R . . C6 C 0.36165(18) 1.2524(2) 0.21071(11) 0.0173(4) Uani 1 1 d . . . H6A H 0.4079 1.2910 0.1673 0.021 Uiso 1 1 calc R . . H6B H 0.4248 1.1749 0.2423 0.021 Uiso 1 1 calc R . . N1 N 0.06068(14) 0.92550(18) 0.13665(8) 0.0143(3) Uani 1 1 d . . . N2 N 0.33458(14) 0.93562(18) 0.11295(8) 0.0143(3) Uani 1 1 d . . . N3 N 0.14982(15) 0.72344(19) 0.03271(9) 0.0175(3) Uani 1 1 d . . . N4 N 0.22471(14) 1.17509(17) 0.18223(8) 0.0127(3) Uani 1 1 d . . . O1 O -0.10525(13) 0.84700(15) 0.01244(7) 0.0170(3) Uani 1 1 d . . . O2 O -0.04885(13) 0.63426(15) 0.10555(7) 0.0175(3) Uani 1 1 d . . . P1 P 0.02329(4) 0.78893(5) 0.07345(2) 0.01211(10) Uani 1 1 d . . . P2 P 0.21636(4) 0.98184(5) 0.16451(2) 0.01071(10) Uani 1 1 d . . . P3 P 0.30124(4) 0.79709(5) 0.05111(2) 0.01337(10) Uani 1 1 d . . . Cl1 Cl 0.27867(5) 0.86891(5) 0.26939(2) 0.01877(11) Uani 1 1 d . . . Cl2 Cl 0.43557(5) 0.60876(6) 0.08009(3) 0.02289(11) Uani 1 1 d . . . Cl3 Cl 0.36538(5) 0.86743(6) -0.04740(3) 0.02621(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0158(9) 0.0218(9) 0.0197(9) 0.0015(7) -0.0044(7) -0.0087(7) C2 0.0121(8) 0.0193(9) 0.0182(8) -0.0021(7) -0.0002(7) -0.0058(7) C3 0.0125(8) 0.0157(8) 0.0242(9) -0.0033(7) 0.0054(7) 0.0012(7) C4 0.0197(9) 0.0135(8) 0.0313(10) -0.0027(8) 0.0070(8) 0.0022(7) C5 0.0227(10) 0.0163(8) 0.0210(9) -0.0032(7) 0.0011(7) -0.0038(7) C6 0.0112(8) 0.0136(8) 0.0257(9) -0.0022(7) -0.0014(7) -0.0009(6) N1 0.0090(7) 0.0173(7) 0.0165(7) -0.0027(6) 0.0015(5) -0.0023(6) N2 0.0104(7) 0.0165(7) 0.0163(7) -0.0054(6) 0.0028(5) -0.0028(5) N3 0.0122(7) 0.0202(8) 0.0199(7) -0.0084(6) 0.0015(6) -0.0051(6) N4 0.0085(7) 0.0107(6) 0.0184(7) -0.0022(6) 0.0008(5) -0.0002(5) O1 0.0123(6) 0.0166(6) 0.0197(6) 0.0042(5) -0.0052(5) -0.0048(5) O2 0.0132(6) 0.0175(6) 0.0201(6) 0.0057(5) -0.0034(5) -0.0058(5) P1 0.0092(2) 0.0134(2) 0.0131(2) 0.00063(16) -0.00063(16) -0.00275(15) P2 0.0094(2) 0.0112(2) 0.0114(2) -0.00161(15) 0.00109(15) -0.00100(15) P3 0.0110(2) 0.0159(2) 0.0135(2) -0.00483(17) 0.00295(16) -0.00321(16) Cl1 0.0234(2) 0.0177(2) 0.0143(2) 0.00308(16) -0.00023(16) 0.00084(16) Cl2 0.0157(2) 0.0191(2) 0.0337(3) -0.00661(18) 0.00300(18) 0.00219(16) Cl3 0.0302(3) 0.0346(3) 0.0159(2) -0.00441(18) 0.01044(18) -0.0100(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.455(2) . ? C1 C2 1.509(2) . ? C2 O2 1.445(2) . ? C3 N4 1.483(2) . ? C3 C4 1.529(2) . ? C4 C5 1.519(3) . ? C5 C6 1.523(2) . ? C6 N4 1.483(2) . ? N1 P2 1.5777(14) . ? N1 P1 1.5782(15) . ? N2 P3 1.5696(15) . ? N2 P2 1.6027(14) . ? N3 P3 1.5690(15) . ? N3 P1 1.5963(15) . ? N4 P2 1.6122(14) . ? O1 P1 1.5859(13) . ? O2 P1 1.5880(12) . ? P2 Cl1 2.0673(6) . ? P3 Cl3 2.0048(6) . ? P3 Cl2 2.0297(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 104.91(14) . . ? O2 C2 C1 104.98(13) . . ? N4 C3 C4 102.10(13) . . ? C5 C4 C3 103.72(15) . . ? C4 C5 C6 103.83(15) . . ? N4 C6 C5 103.93(14) . . ? P2 N1 P1 122.17(9) . . ? P3 N2 P2 118.09(9) . . ? P3 N3 P1 121.96(9) . . ? C3 N4 C6 111.47(13) . . ? C3 N4 P2 123.39(11) . . ? C6 N4 P2 120.03(11) . . ? C1 O1 P1 109.60(11) . . ? C2 O2 P1 111.47(11) . . ? N1 P1 O1 109.63(8) . . ? N1 P1 O2 112.48(7) . . ? O1 P1 O2 97.96(7) . . ? N1 P1 N3 116.26(8) . . ? O1 P1 N3 111.82(8) . . ? O2 P1 N3 107.19(8) . . ? N1 P2 N2 118.73(8) . . ? N1 P2 N4 111.39(8) . . ? N2 P2 N4 108.74(8) . . ? N1 P2 Cl1 106.41(6) . . ? N2 P2 Cl1 105.05(6) . . ? N4 P2 Cl1 105.52(6) . . ? N3 P3 N2 120.59(8) . . ? N3 P3 Cl3 109.29(6) . . ? N2 P3 Cl3 109.30(6) . . ? N3 P3 Cl2 107.45(6) . . ? N2 P3 Cl2 108.55(6) . . ? Cl3 P3 Cl2 99.60(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.353 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.079