# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Simon J. Coles' _publ_contact_author_email S.J.Coles@soton.ac.uk loop_ _publ_author_name 'Serap Besli' 'Simon J. Coles' 'David B. Davies' 'Adem Kilic' 'Elif Okutan' 'Robert A. Shaw' ; E.T.Ecik ; 'Gonul Yenilmez Ciftci' data_2006src1518r _database_code_depnum_ccdc_archive 'CCDC 809127' #TrackingRef '10a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 Cl3 N5 O P3' _chemical_formula_weight 384.50 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 12.7916(4) _cell_length_b 17.6220(5) _cell_length_c 15.4171(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.007(2) _cell_angle_gamma 90.00 _cell_volume 3174.60(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 82060 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8440 _exptl_absorpt_correction_T_max 0.8440 _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 32010 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3643 _reflns_number_gt 2745 _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^)+(0.0752P)^2^+4.8207P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3643 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.056 _refine_ls_shift/su_mean 0.030 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 0.4863(4) -0.0936(2) 0.1030(3) 0.0848(13) Uani 1 1 d . . . H1A H 0.4518 -0.0853 0.0335 0.102 Uiso 1 1 calc R . . H1B H 0.4243 -0.1109 0.1212 0.102 Uiso 1 1 calc R . . C2 C 0.5684(4) -0.1545(2) 0.1231(4) 0.0909(14) Uani 1 1 d . . . H2A H 0.5403 -0.1972 0.1494 0.109 Uiso 1 1 calc R . . H2B H 0.5675 -0.1718 0.0617 0.109 Uiso 1 1 calc R . . C3 C 0.6827(4) -0.1415(2) 0.1846(5) 0.115(2) Uani 1 1 d . . . H3A H 0.6934 -0.1620 0.2475 0.137 Uiso 1 1 calc R . . H3B H 0.7305 -0.1727 0.1616 0.137 Uiso 1 1 calc R . . C4 C 0.8385(4) 0.0259(2) 0.5162(2) 0.0684(10) Uani 1 1 d . . . H4A H 0.8392 -0.0255 0.4904 0.082 Uiso 1 1 calc R . . H4B H 0.7660 0.0330 0.5239 0.082 Uiso 1 1 calc R . . C5 C 0.9403(4) 0.0373(2) 0.6092(3) 0.0730(10) Uani 1 1 d . . . H5A H 0.9208 0.0242 0.6633 0.088 Uiso 1 1 calc R . . H5B H 1.0054 0.0054 0.6124 0.088 Uiso 1 1 calc R . . C6 C 0.9686(5) 0.1184(3) 0.6110(3) 0.109(2) Uani 1 1 d . . . H6A H 1.0521 0.1260 0.6462 0.131 Uiso 1 1 calc R . . H6B H 0.9287 0.1478 0.6432 0.131 Uiso 1 1 calc R . . C7 C 0.9318(3) 0.1449(2) 0.5113(2) 0.0651(9) Uani 1 1 d . . . H7A H 0.8922 0.1944 0.5019 0.078 Uiso 1 1 calc R . . H7B H 0.9983 0.1500 0.4944 0.078 Uiso 1 1 calc R . . N1 N 0.6828(2) 0.02965(15) 0.30466(19) 0.0566(7) Uani 1 1 d . . . N2 N 0.7983(2) 0.15615(14) 0.29129(17) 0.0497(6) Uani 1 1 d . . . N3 N 0.6933(2) 0.06424(16) 0.13973(18) 0.0575(7) Uani 1 1 d . . . N4 N 0.5258(2) -0.02344(17) 0.1469(3) 0.0711(9) Uani 1 1 d D . . N5 N 0.8526(2) 0.08510(14) 0.45341(17) 0.0495(6) Uani 1 1 d . . . O1 O 0.7270(2) -0.07016(13) 0.1990(2) 0.0725(7) Uani 1 1 d . . . P1 P 0.65760(7) 0.00325(4) 0.19947(6) 0.0484(2) Uani 1 1 d . . . P2 P 0.75116(7) 0.10376(4) 0.35166(5) 0.0443(2) Uani 1 1 d . . . P3 P 0.75262(7) 0.14107(4) 0.18169(5) 0.0449(2) Uani 1 1 d . . . Cl1 Cl 0.63792(10) 0.17052(7) 0.38131(8) 0.0837(3) Uani 1 1 d . . . Cl2 Cl 0.64757(11) 0.22638(6) 0.11138(8) 0.0931(4) Uani 1 1 d . . . Cl3 Cl 0.88050(10) 0.15964(7) 0.14171(8) 0.0860(4) Uani 1 1 d . . . H4N H 0.470(3) 0.005(2) 0.158(3) 0.112(15) 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 0.067(2) 0.064(2) 0.091(3) -0.029(2) -0.001(2) -0.0095(19) C2 0.086(3) 0.049(2) 0.121(4) -0.031(2) 0.025(3) -0.013(2) C3 0.080(3) 0.039(2) 0.196(6) 0.001(3) 0.026(3) 0.009(2) C4 0.090(3) 0.061(2) 0.0506(18) 0.0085(16) 0.0256(18) -0.0206(19) C5 0.078(2) 0.081(3) 0.055(2) 0.0179(19) 0.0222(18) -0.005(2) C6 0.140(5) 0.099(3) 0.049(2) 0.007(2) -0.001(2) -0.048(3) C7 0.071(2) 0.064(2) 0.0506(18) -0.0043(15) 0.0148(16) -0.0237(17) N1 0.0656(17) 0.0506(15) 0.0545(15) -0.0085(12) 0.0253(13) -0.0222(13) N2 0.0641(16) 0.0424(12) 0.0381(12) -0.0056(10) 0.0161(11) -0.0155(11) N3 0.0716(18) 0.0534(15) 0.0481(14) -0.0159(12) 0.0250(13) -0.0143(13) N4 0.0405(14) 0.0549(17) 0.106(3) -0.0307(16) 0.0176(15) -0.0036(13) N5 0.0591(15) 0.0460(13) 0.0402(13) 0.0005(10) 0.0169(11) -0.0106(11) O1 0.0493(12) 0.0465(12) 0.112(2) -0.0219(13) 0.0225(13) 0.0023(10) P1 0.0425(4) 0.0379(4) 0.0604(5) -0.0138(3) 0.0166(3) -0.0037(3) P2 0.0516(4) 0.0406(4) 0.0417(4) -0.0052(3) 0.0202(3) -0.0065(3) P3 0.0516(4) 0.0418(4) 0.0387(4) -0.0022(3) 0.0157(3) -0.0024(3) Cl1 0.0844(7) 0.0859(7) 0.0911(7) -0.0103(5) 0.0462(6) 0.0219(5) Cl2 0.1020(8) 0.0629(6) 0.0759(7) 0.0078(5) -0.0033(6) 0.0225(5) Cl3 0.0939(7) 0.0986(8) 0.0888(7) -0.0152(6) 0.0610(6) -0.0289(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 N4 1.402(4) . ? C1 C2 1.443(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.400(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.360(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N5 1.483(4) . ? C4 C5 1.508(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.473(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.487(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N5 1.482(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 P2 1.575(3) . ? N1 P1 1.589(3) . ? N2 P3 1.570(2) . ? N2 P2 1.593(3) . ? N3 P3 1.558(3) . ? N3 P1 1.598(3) . ? N4 P1 1.615(3) . ? N4 H4N 0.938(10) . ? N5 P2 1.611(3) . ? O1 P1 1.571(2) . ? P1 H4N 2.21(3) . ? P2 Cl1 2.0568(12) . ? P3 Cl3 1.9958(12) . ? P3 Cl2 2.0137(12) . ? 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 117.6(3) . . ? N4 C1 H1A 107.9 . . ? C2 C1 H1A 107.9 . . ? N4 C1 H1B 107.9 . . ? C2 C1 H1B 107.9 . . ? H1A C1 H1B 107.2 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2A 107.4 . . ? C1 C2 H2A 107.4 . . ? C3 C2 H2B 107.5 . . ? C1 C2 H2B 107.5 . . ? H2A C2 H2B 107.0 . . ? O1 C3 C2 120.8(4) . . ? O1 C3 H3A 107.1 . . ? C2 C3 H3A 107.1 . . ? O1 C3 H3B 107.1 . . ? C2 C3 H3B 107.1 . . ? H3A C3 H3B 106.8 . . ? N5 C4 C5 103.9(3) . . ? N5 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? N5 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C4 104.9(3) . . ? C6 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? C6 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.8 . . ? C5 C6 C7 108.2(3) . . ? C5 C6 H6A 110.0 . . ? C7 C6 H6A 110.1 . . ? C5 C6 H6B 110.1 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N5 C7 C6 104.6(3) . . ? N5 C7 H7A 110.8 . . ? C6 C7 H7A 110.8 . . ? N5 C7 H7B 110.8 . . ? C6 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? P2 N1 P1 123.79(17) . . ? P3 N2 P2 117.86(15) . . ? P3 N3 P1 123.37(16) . . ? C1 N4 P1 126.7(3) . . ? C1 N4 H4N 114(3) . . ? P1 N4 H4N 118(3) . . ? C7 N5 C4 110.0(2) . . ? C7 N5 P2 121.6(2) . . ? C4 N5 P2 121.0(2) . . ? C3 O1 P1 124.3(3) . . ? O1 P1 N1 111.44(17) . . ? O1 P1 N3 104.88(16) . . ? N1 P1 N3 113.87(13) . . ? O1 P1 N4 103.56(14) . . ? N1 P1 N4 109.51(17) . . ? N3 P1 N4 113.04(18) . . ? O1 P1 H4N 123.8(10) . . ? N1 P1 H4N 92.2(11) . . ? N3 P1 H4N 110.7(13) . . ? N4 P1 H4N 22.0(10) . . ? N1 P2 N2 118.90(13) . . ? N1 P2 N5 110.81(14) . . ? N2 P2 N5 109.92(14) . . ? N1 P2 Cl1 105.48(12) . . ? N2 P2 Cl1 105.45(11) . . ? N5 P2 Cl1 105.15(11) . . ? N3 P3 N2 119.94(14) . . ? N3 P3 Cl3 109.63(11) . . ? N2 P3 Cl3 108.19(11) . . ? N3 P3 Cl2 108.64(12) . . ? N2 P3 Cl2 109.13(11) . . ? Cl3 P3 Cl2 99.36(7) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.350 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.067 # Attachment '10b.cif' data_2005src0263 _database_code_depnum_ccdc_archive 'CCDC 809128' #TrackingRef '10b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 Cl3 N5 O P3' _chemical_formula_weight 384.50 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2456(6) _cell_length_b 11.8383(7) _cell_length_c 15.3172(14) _cell_angle_alpha 78.702(6) _cell_angle_beta 76.806(7) _cell_angle_gamma 67.964(7) _cell_volume 1501.67(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6696 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8733 _exptl_absorpt_correction_T_max 0.9129 _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 29200 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6866 _reflns_number_gt 5550 _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^)+(0.0374P)^2^+1.2386P] 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 0.0020(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6866 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H9N H 0.802(3) 0.103(2) 0.3754(18) 0.017(7) Uiso 1 1 d . . . H4N H 0.705(3) 0.697(2) 0.1308(17) 0.011(7) Uiso 1 1 d . . . C1 C 0.7768(3) 0.6943(2) 0.00389(16) 0.0206(5) Uani 1 1 d . . . H1A H 0.8913 0.6468 0.0006 0.025 Uiso 1 1 calc R . . H1B H 0.7631 0.7826 -0.0101 0.025 Uiso 1 1 calc R . . C2 C 0.7123(3) 0.6575(2) -0.06452(15) 0.0195(5) Uani 1 1 d . . . H2A H 0.5999 0.7097 -0.0642 0.023 Uiso 1 1 calc R . . H2B H 0.7719 0.6714 -0.1257 0.023 Uiso 1 1 calc R . . C3 C 0.7254(3) 0.5239(2) -0.04376(15) 0.0204(5) Uani 1 1 d . . . H3A H 0.6837 0.5022 -0.0898 0.025 Uiso 1 1 calc R . . H3B H 0.8379 0.4709 -0.0456 0.025 Uiso 1 1 calc R . . C4 C 0.2870(3) 0.5878(2) 0.38184(17) 0.0216(5) Uani 1 1 d . . . H4A H 0.2580 0.6074 0.3209 0.026 Uiso 1 1 calc R . . H4B H 0.2940 0.6619 0.3988 0.026 Uiso 1 1 calc R . . C5 C 0.1680(3) 0.5430(3) 0.45043(19) 0.0321(6) Uani 1 1 d . . . H5A H 0.0798 0.6125 0.4767 0.038 Uiso 1 1 calc R . . H5B H 0.1244 0.4966 0.4227 0.038 Uiso 1 1 calc R . . C6 C 0.2634(3) 0.4607(2) 0.52135(17) 0.0276(6) Uani 1 1 d . . . H6A H 0.2130 0.4014 0.5564 0.033 Uiso 1 1 calc R . . H6B H 0.2744 0.5095 0.5634 0.033 Uiso 1 1 calc R . . C7 C 0.4240(3) 0.3944(2) 0.46706(15) 0.0192(5) Uani 1 1 d . . . H7A H 0.5103 0.3764 0.5015 0.023 Uiso 1 1 calc R . . H7B H 0.4265 0.3166 0.4511 0.023 Uiso 1 1 calc R . . C8 C 0.7302(3) -0.1307(2) 0.54490(16) 0.0221(5) Uani 1 1 d . . . H8A H 0.7463 -0.2027 0.5919 0.026 Uiso 1 1 calc R . . H8B H 0.6154 -0.0927 0.5428 0.026 Uiso 1 1 calc R . . C9 C 0.7890(3) -0.0394(2) 0.56792(16) 0.0226(5) Uani 1 1 d . . . H9A H 0.9049 -0.0759 0.5663 0.027 Uiso 1 1 calc R . . H9B H 0.7382 -0.0188 0.6298 0.027 Uiso 1 1 calc R . . C10 C 0.7511(3) 0.0762(2) 0.50148(16) 0.0227(5) Uani 1 1 d . . . H10A H 0.6349 0.1173 0.5076 0.027 Uiso 1 1 calc R . . H10B H 0.7960 0.1334 0.5151 0.027 Uiso 1 1 calc R . . C11 C 1.0822(3) -0.1668(2) 0.03287(16) 0.0195(5) Uani 1 1 d . . . H11A H 1.0040 -0.1016 -0.0008 0.023 Uiso 1 1 calc R . . H11B H 1.0657 -0.2456 0.0364 0.023 Uiso 1 1 calc R . . C12 C 1.2513(3) -0.1765(3) -0.01250(19) 0.0326(6) Uani 1 1 d . . . H12A H 1.3208 -0.2635 -0.0139 0.039 Uiso 1 1 calc R . . H12B H 1.2532 -0.1346 -0.0752 0.039 Uiso 1 1 calc R . . C13 C 1.3052(3) -0.1135(2) 0.04531(17) 0.0233(5) Uani 1 1 d . . . H13A H 1.4219 -0.1455 0.0400 0.028 Uiso 1 1 calc R . . H13B H 1.2689 -0.0235 0.0280 0.028 Uiso 1 1 calc R . . C14 C 1.2264(3) -0.1465(2) 0.14011(17) 0.0227(5) Uani 1 1 d . . . H14A H 1.2851 -0.2311 0.1651 0.027 Uiso 1 1 calc R . . H14B H 1.2174 -0.0884 0.1813 0.027 Uiso 1 1 calc R . . N1 N 0.5374(2) 0.53995(17) 0.21225(13) 0.0167(4) Uani 1 1 d . . . N2 N 0.7149(2) 0.33394(17) 0.30866(13) 0.0180(4) Uani 1 1 d . . . N3 N 0.8491(2) 0.43294(18) 0.14873(13) 0.0197(4) Uani 1 1 d . . . O1 O 0.6351(2) 0.50325(14) 0.04597(10) 0.0184(3) Uani 1 1 d . . . N5 N 0.4396(2) 0.48306(17) 0.38423(12) 0.0160(4) Uani 1 1 d . . . N6 N 0.9538(2) -0.12440(19) 0.29666(14) 0.0210(4) Uani 1 1 d . . . N7 N 0.7707(2) -0.12695(18) 0.17937(13) 0.0179(4) Uani 1 1 d . . . N8 N 0.6352(2) -0.03351(18) 0.34029(13) 0.0197(4) Uani 1 1 d . . . N9 N 0.8175(3) 0.0469(2) 0.40802(14) 0.0201(4) Uani 1 1 d . . . N10 N 1.0678(2) -0.13562(18) 0.12518(13) 0.0179(4) Uani 1 1 d . . . N4 N 0.6912(2) 0.67040(18) 0.09617(14) 0.0164(4) Uani 1 1 d . . . O2 O 0.8168(2) -0.16965(14) 0.45723(11) 0.0208(4) Uani 1 1 d . . . P1 P 0.67962(7) 0.53391(5) 0.12995(4) 0.01460(13) Uani 1 1 d . . . P2 P 0.54447(7) 0.43048(5) 0.29069(4) 0.01455(13) Uani 1 1 d . . . P3 P 0.86451(7) 0.33572(5) 0.23457(4) 0.01563(13) Uani 1 1 d . . . P4 P 0.80521(7) -0.06984(5) 0.37165(4) 0.01701(14) Uani 1 1 d . . . P5 P 0.94127(7) -0.16846(5) 0.20910(4) 0.01657(14) Uani 1 1 d . . . P6 P 0.62030(7) -0.07928(5) 0.25467(4) 0.01589(14) Uani 1 1 d . . . Cl1 Cl 0.43344(8) 0.32543(6) 0.25917(4) 0.02568(15) Uani 1 1 d . . . Cl2 Cl 1.02760(7) 0.34163(6) 0.29982(4) 0.02408(14) Uani 1 1 d . . . Cl3 Cl 0.97617(8) 0.16610(5) 0.19513(4) 0.02644(15) Uani 1 1 d . . . Cl4 Cl 1.01180(8) -0.35782(5) 0.22863(4) 0.02450(14) Uani 1 1 d . . . Cl5 Cl 0.45257(7) 0.05147(5) 0.19155(4) 0.02257(14) Uani 1 1 d . . . Cl6 Cl 0.51797(7) -0.20994(5) 0.29463(4) 0.02288(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 0.0194(13) 0.0229(12) 0.0189(12) -0.0008(9) 0.0000(10) -0.0094(10) C2 0.0176(12) 0.0265(12) 0.0122(11) 0.0000(9) -0.0006(9) -0.0076(10) C3 0.0210(13) 0.0264(13) 0.0129(12) -0.0046(9) -0.0007(10) -0.0072(10) C4 0.0152(12) 0.0213(12) 0.0225(13) -0.0012(10) -0.0017(10) -0.0014(10) C5 0.0200(14) 0.0388(16) 0.0306(15) -0.0011(12) 0.0004(12) -0.0066(12) C6 0.0234(14) 0.0342(14) 0.0215(13) -0.0022(11) 0.0019(11) -0.0097(12) C7 0.0203(13) 0.0229(12) 0.0137(12) 0.0001(9) -0.0033(10) -0.0076(10) C8 0.0179(13) 0.0307(13) 0.0146(12) 0.0042(10) -0.0026(10) -0.0086(11) C9 0.0194(13) 0.0324(14) 0.0153(12) -0.0036(10) -0.0015(10) -0.0087(11) C10 0.0230(13) 0.0250(13) 0.0214(13) -0.0089(10) -0.0012(10) -0.0084(11) C11 0.0183(12) 0.0230(12) 0.0183(12) -0.0039(9) -0.0008(10) -0.0089(10) C12 0.0254(15) 0.0488(17) 0.0265(15) -0.0105(12) 0.0032(12) -0.0177(13) C13 0.0150(12) 0.0248(13) 0.0297(14) -0.0035(10) -0.0003(10) -0.0082(10) C14 0.0163(12) 0.0266(13) 0.0269(14) -0.0059(10) -0.0051(10) -0.0071(10) N1 0.0137(10) 0.0186(10) 0.0155(10) -0.0007(7) -0.0007(8) -0.0049(8) N2 0.0153(10) 0.0195(10) 0.0157(10) 0.0020(7) -0.0008(8) -0.0052(8) N3 0.0173(11) 0.0219(10) 0.0148(10) 0.0026(8) -0.0012(8) -0.0043(8) O1 0.0241(9) 0.0192(8) 0.0142(8) -0.0007(6) -0.0046(7) -0.0099(7) N5 0.0144(10) 0.0195(10) 0.0137(10) -0.0018(7) -0.0014(8) -0.0060(8) N6 0.0157(10) 0.0286(11) 0.0213(11) -0.0080(8) -0.0035(8) -0.0081(9) N7 0.0139(10) 0.0239(10) 0.0163(10) -0.0057(8) -0.0002(8) -0.0071(8) N8 0.0172(10) 0.0234(10) 0.0189(10) -0.0078(8) -0.0012(8) -0.0059(8) N9 0.0295(12) 0.0206(11) 0.0132(10) 0.0003(9) -0.0032(9) -0.0135(9) N10 0.0127(10) 0.0246(10) 0.0180(10) -0.0052(8) -0.0014(8) -0.0078(8) N4 0.0197(11) 0.0186(10) 0.0127(10) -0.0034(8) -0.0011(8) -0.0089(8) O2 0.0237(9) 0.0192(8) 0.0185(9) -0.0021(6) -0.0029(7) -0.0067(7) P1 0.0139(3) 0.0160(3) 0.0137(3) -0.0008(2) -0.0024(2) -0.0054(2) P2 0.0133(3) 0.0172(3) 0.0138(3) -0.0009(2) -0.0020(2) -0.0067(2) P3 0.0140(3) 0.0166(3) 0.0143(3) 0.0000(2) -0.0021(2) -0.0042(2) P4 0.0175(3) 0.0191(3) 0.0162(3) -0.0039(2) -0.0021(2) -0.0078(2) P5 0.0151(3) 0.0191(3) 0.0167(3) -0.0043(2) -0.0018(2) -0.0066(2) P6 0.0140(3) 0.0178(3) 0.0165(3) -0.0038(2) -0.0016(2) -0.0059(2) Cl1 0.0329(4) 0.0331(3) 0.0212(3) -0.0039(2) -0.0053(3) -0.0220(3) Cl2 0.0190(3) 0.0320(3) 0.0221(3) 0.0010(2) -0.0073(2) -0.0097(3) Cl3 0.0305(4) 0.0189(3) 0.0231(3) -0.0044(2) 0.0029(3) -0.0043(3) Cl4 0.0284(3) 0.0188(3) 0.0255(3) -0.0018(2) -0.0056(3) -0.0073(2) Cl5 0.0185(3) 0.0227(3) 0.0238(3) -0.0005(2) -0.0056(2) -0.0040(2) Cl6 0.0257(3) 0.0226(3) 0.0229(3) -0.0044(2) 0.0015(2) -0.0137(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 N4 1.485(3) . ? C1 C2 1.517(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.515(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.464(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N5 1.491(3) . ? C4 C5 1.513(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.512(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N5 1.496(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.460(3) . ? C8 C9 1.506(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.513(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N9 1.477(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N10 1.495(3) . ? C11 C12 1.530(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.525(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.517(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N10 1.490(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N1 P2 1.5779(19) . ? N1 P1 1.591(2) . ? N2 P3 1.580(2) . ? N2 P2 1.609(2) . ? N3 P3 1.5631(19) . ? N3 P1 1.622(2) . ? O1 P1 1.5790(16) . ? N5 P2 1.6257(19) . ? N6 P5 1.573(2) . ? N6 P4 1.590(2) . ? N7 P6 1.586(2) . ? N7 P5 1.611(2) . ? N8 P6 1.5651(19) . ? N8 P4 1.626(2) . ? N9 P4 1.637(2) . ? N9 H9N 0.74(3) . ? N10 P5 1.622(2) . ? N4 P1 1.633(2) . ? N4 H4N 0.73(3) . ? O2 P4 1.5774(17) . ? P2 Cl1 2.0622(8) . ? P3 Cl2 2.0179(8) . ? P3 Cl3 2.0244(8) . ? P5 Cl4 2.0662(8) . ? P6 Cl5 2.0081(8) . ? P6 Cl6 2.0310(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 N4 C1 C2 109.69(19) . . ? N4 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N4 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C3 C2 C1 111.54(19) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O1 C3 C2 109.57(18) . . ? O1 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? O1 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N5 C4 C5 104.21(19) . . ? N5 C4 H4A 110.9 . . ? C5 C4 H4A 110.9 . . ? N5 C4 H4B 110.9 . . ? C5 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C6 C5 C4 103.7(2) . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5B 111.0 . . ? C4 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C5 C6 C7 104.1(2) . . ? C5 C6 H6A 110.9 . . ? C7 C6 H6A 110.9 . . ? C5 C6 H6B 110.9 . . ? C7 C6 H6B 110.9 . . ? H6A C6 H6B 109.0 . . ? N5 C7 C6 104.06(19) . . ? N5 C7 H7A 110.9 . . ? C6 C7 H7A 110.9 . . ? N5 C7 H7B 110.9 . . ? C6 C7 H7B 110.9 . . ? H7A C7 H7B 109.0 . . ? O2 C8 C9 109.23(19) . . ? O2 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? O2 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C8 C9 C10 110.4(2) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N9 C10 C9 110.6(2) . . ? N9 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N10 C11 C12 104.36(19) . . ? N10 C11 H11A 110.9 . . ? C12 C11 H11A 110.9 . . ? N10 C11 H11B 110.9 . . ? C12 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? C13 C12 C11 105.1(2) . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 102.9(2) . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? N10 C14 C13 102.06(19) . . ? N10 C14 H14A 111.4 . . ? C13 C14 H14A 111.4 . . ? N10 C14 H14B 111.4 . . ? C13 C14 H14B 111.4 . . ? H14A C14 H14B 109.2 . . ? P2 N1 P1 122.06(12) . . ? P3 N2 P2 118.07(12) . . ? P3 N3 P1 122.01(13) . . ? C3 O1 P1 118.53(14) . . ? C4 N5 C7 109.60(18) . . ? C4 N5 P2 119.61(15) . . ? C7 N5 P2 119.14(15) . . ? P5 N6 P4 123.31(13) . . ? P6 N7 P5 116.62(12) . . ? P6 N8 P4 121.70(12) . . ? C10 N9 P4 122.24(17) . . ? C10 N9 H9N 111(2) . . ? P4 N9 H9N 114(2) . . ? C14 N10 C11 109.33(18) . . ? C14 N10 P5 120.03(16) . . ? C11 N10 P5 121.20(15) . . ? C1 N4 P1 118.60(16) . . ? C1 N4 H4N 115(2) . . ? P1 N4 H4N 114(2) . . ? C8 O2 P4 118.65(14) . . ? O1 P1 N1 108.05(10) . . ? O1 P1 N3 108.58(10) . . ? N1 P1 N3 114.68(10) . . ? O1 P1 N4 103.05(10) . . ? N1 P1 N4 110.12(10) . . ? N3 P1 N4 111.64(11) . . ? N1 P2 N2 118.66(10) . . ? N1 P2 N5 109.98(10) . . ? N2 P2 N5 109.99(10) . . ? N1 P2 Cl1 107.43(8) . . ? N2 P2 Cl1 104.33(8) . . ? N5 P2 Cl1 105.48(7) . . ? N3 P3 N2 121.09(11) . . ? N3 P3 Cl2 110.01(8) . . ? N2 P3 Cl2 106.67(8) . . ? N3 P3 Cl3 108.80(8) . . ? N2 P3 Cl3 108.65(8) . . ? Cl2 P3 Cl3 99.44(4) . . ? O2 P4 N6 107.34(10) . . ? O2 P4 N8 109.41(10) . . ? N6 P4 N8 114.16(10) . . ? O2 P4 N9 103.70(10) . . ? N6 P4 N9 110.89(11) . . ? N8 P4 N9 110.75(11) . . ? N6 P5 N7 119.22(11) . . ? N6 P5 N10 109.34(11) . . ? N7 P5 N10 110.14(10) . . ? N6 P5 Cl4 108.16(8) . . ? N7 P5 Cl4 103.31(8) . . ? N10 P5 Cl4 105.69(8) . . ? N8 P6 N7 120.51(11) . . ? N8 P6 Cl5 110.06(8) . . ? N7 P6 Cl5 106.79(8) . . ? N8 P6 Cl6 109.00(8) . . ? N7 P6 Cl6 108.65(8) . . ? Cl5 P6 Cl6 99.85(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.823 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.085 # Attachment '3a.cif' data_2006src0262 _database_code_depnum_ccdc_archive 'CCDC 809129' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H13 Cl3 N5 O P3' _chemical_formula_weight 358.46 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 12.6777(4) _cell_length_b 6.7209(2) _cell_length_c 16.6315(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.214(2) _cell_angle_gamma 90.00 _cell_volume 1411.23(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3441 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6951 _exptl_absorpt_correction_T_max 0.9903 _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 19083 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3236 _reflns_number_gt 2725 _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^)+(0.0556P)^2^+4.6030P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3236 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.9364(4) -0.1459(10) 0.3549(3) 0.0595(15) Uani 1 1 d . . . H1A H 0.9627 -0.2164 0.3091 0.089 Uiso 1 1 calc R . . H1B H 0.9386 -0.2351 0.4016 0.089 Uiso 1 1 calc R . . H1C H 0.9811 -0.0295 0.3684 0.089 Uiso 1 1 calc R . . C2 C 0.6147(3) 0.4348(6) 0.1243(2) 0.0304(8) Uani 1 1 d . . . H2A H 0.6280 0.4158 0.0677 0.046 Uiso 1 1 calc R . . H2B H 0.6819 0.4297 0.1583 0.046 Uiso 1 1 calc R . . H2C H 0.5810 0.5645 0.1306 0.046 Uiso 1 1 calc R . . C3 C 0.4407(3) 0.2785(5) 0.0984(2) 0.0228(7) Uani 1 1 d . . . H3A H 0.4532 0.2575 0.0411 0.027 Uiso 1 1 calc R . . H3B H 0.4072 0.4107 0.1028 0.027 Uiso 1 1 calc R . . C4 C 0.3660(3) 0.1200(6) 0.1239(2) 0.0227(7) Uani 1 1 d . . . H4A H 0.3488 0.1467 0.1798 0.027 Uiso 1 1 calc R . . H4B H 0.2992 0.1250 0.0882 0.027 Uiso 1 1 calc R . . C5 C 0.4141(3) -0.0847(5) 0.1199(2) 0.0216(7) Uani 1 1 d . . . H5A H 0.3617 -0.1859 0.1332 0.026 Uiso 1 1 calc R . . H5B H 0.4329 -0.1106 0.0643 0.026 Uiso 1 1 calc R . . N1 N 0.6759(2) 0.0755(5) 0.25138(16) 0.0213(6) Uani 1 1 d . . . N2 N 0.8574(2) -0.0017(6) 0.18210(18) 0.0301(7) Uani 1 1 d . . . N3 N 0.6686(2) -0.0021(4) 0.09148(16) 0.0195(6) Uani 1 1 d . . . N4 N 0.5444(2) 0.2767(4) 0.14865(17) 0.0202(6) Uani 1 1 d . . . N5 N 0.5102(2) -0.1008(4) 0.17722(18) 0.0192(6) Uani 1 1 d . . . O1 O 0.8340(2) -0.0852(5) 0.33459(16) 0.0374(7) Uani 1 1 d . . . P1 P 0.60415(6) 0.05979(13) 0.16752(5) 0.0165(2) Uani 1 1 d . . . P2 P 0.79927(7) 0.05879(16) 0.25918(5) 0.0253(2) Uani 1 1 d . . . P3 P 0.79051(7) -0.03017(14) 0.09852(5) 0.0208(2) Uani 1 1 d . . . Cl1 Cl 0.86255(8) 0.32199(19) 0.29796(7) 0.0451(3) Uani 1 1 d . . . Cl2 Cl 0.82733(8) -0.30100(16) 0.05622(6) 0.0355(3) Uani 1 1 d . . . Cl3 Cl 0.85318(8) 0.14363(16) 0.01658(6) 0.0333(2) Uani 1 1 d . . . H5N H 0.501(4) -0.129(8) 0.226(3) 0.042(14) 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 0.037(3) 0.096(5) 0.046(3) 0.018(3) 0.007(2) 0.010(3) C2 0.034(2) 0.0218(19) 0.036(2) 0.0021(16) 0.0055(17) -0.0017(15) C3 0.0250(17) 0.0240(18) 0.0187(16) -0.0004(13) -0.0015(13) 0.0081(14) C4 0.0190(16) 0.0315(19) 0.0172(16) -0.0014(14) -0.0010(12) 0.0041(14) C5 0.0189(16) 0.0280(19) 0.0172(16) 0.0011(13) -0.0023(13) -0.0015(13) N1 0.0199(14) 0.0311(16) 0.0132(13) -0.0030(11) 0.0021(11) 0.0025(12) N2 0.0166(14) 0.053(2) 0.0210(15) -0.0074(14) 0.0010(12) 0.0039(14) N3 0.0168(13) 0.0265(15) 0.0150(13) -0.0019(11) 0.0007(10) 0.0023(11) N4 0.0224(14) 0.0186(14) 0.0199(14) 0.0003(11) 0.0032(11) 0.0013(11) N5 0.0173(13) 0.0231(15) 0.0168(14) 0.0027(11) -0.0005(11) 0.0009(11) O1 0.0424(17) 0.0505(19) 0.0204(13) 0.0107(13) 0.0087(12) 0.0038(14) P1 0.0159(4) 0.0203(4) 0.0134(4) -0.0005(3) 0.0014(3) 0.0020(3) P2 0.0179(4) 0.0417(6) 0.0160(4) -0.0044(4) -0.0008(3) 0.0012(4) P3 0.0161(4) 0.0296(5) 0.0170(4) -0.0045(3) 0.0031(3) 0.0008(3) Cl1 0.0348(5) 0.0626(8) 0.0389(6) -0.0223(5) 0.0092(4) -0.0210(5) Cl2 0.0327(5) 0.0371(6) 0.0374(5) -0.0030(4) 0.0066(4) 0.0069(4) Cl3 0.0326(5) 0.0425(6) 0.0260(5) -0.0005(4) 0.0089(4) -0.0135(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 1.374(6) . ? C2 N4 1.467(5) . ? C3 N4 1.492(4) . ? C3 C4 1.512(5) . ? C4 C5 1.508(5) . ? C5 N5 1.481(4) . ? N1 P2 1.562(3) . ? N1 P1 1.598(3) . ? N2 P3 1.573(3) . ? N2 P2 1.589(3) . ? N3 P3 1.550(3) . ? N3 P1 1.621(3) . ? N4 P1 1.660(3) . ? N5 P1 1.627(3) . ? O1 P2 1.613(3) . ? P2 Cl1 2.0235(15) . ? P3 Cl3 2.0123(13) . ? P3 Cl2 2.0213(14) . ? 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 C3 C4 112.3(3) . . ? C5 C4 C3 111.3(3) . . ? N5 C5 C4 110.5(3) . . ? P2 N1 P1 123.65(18) . . ? P3 N2 P2 119.45(19) . . ? P3 N3 P1 122.82(18) . . ? C2 N4 C3 111.5(3) . . ? C2 N4 P1 114.2(2) . . ? C3 N4 P1 118.5(2) . . ? C5 N5 P1 117.0(2) . . ? C1 O1 P2 123.6(3) . . ? N1 P1 N3 114.23(15) . . ? N1 P1 N5 108.73(15) . . ? N3 P1 N5 109.45(16) . . ? N1 P1 N4 108.73(16) . . ? N3 P1 N4 109.37(15) . . ? N5 P1 N4 106.00(15) . . ? N1 P2 N2 119.08(16) . . ? N1 P2 O1 107.94(16) . . ? N2 P2 O1 111.09(17) . . ? N1 P2 Cl1 109.20(13) . . ? N2 P2 Cl1 106.34(14) . . ? O1 P2 Cl1 101.79(13) . . ? N3 P3 N2 120.37(16) . . ? N3 P3 Cl3 109.29(12) . . ? N2 P3 Cl3 108.27(14) . . ? N3 P3 Cl2 110.09(12) . . ? N2 P3 Cl2 107.10(14) . . ? Cl3 P3 Cl2 99.74(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.926 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.112 # Attachment '5a.cif' data_2007src0927 _database_code_depnum_ccdc_archive 'CCDC 809130' #TrackingRef '5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H15 Cl3 N5 O P3' _chemical_formula_weight 420.53 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.68270(10) _cell_length_b 22.3776(2) _cell_length_c 16.0124(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.8460(10) _cell_angle_gamma 90.00 _cell_volume 3467.70(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 57249 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8545 _exptl_absorpt_correction_T_max 0.9683 _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 APEX2 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 35212 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 15188 _reflns_number_gt 14428 _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, 2003)' _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^)+(0.0197P)^2^+2.3106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.44(3) _refine_ls_number_reflns 15188 _refine_ls_number_parameters 814 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 1.0396(4) 0.23800(13) 0.2323(2) 0.0339(7) Uani 1 1 d . . . H1A H 0.9446 0.2528 0.2252 0.051 Uiso 1 1 calc R . . H1B H 1.0827 0.2364 0.1778 0.051 Uiso 1 1 calc R . . H1C H 1.0925 0.2650 0.2694 0.051 Uiso 1 1 calc R . . C2 C 0.9763(3) 0.17593(14) 0.35196(18) 0.0277(6) Uani 1 1 d . . . H2A H 0.8753 0.1821 0.3455 0.033 Uiso 1 1 calc R . . H2B H 1.0146 0.2089 0.3868 0.033 Uiso 1 1 calc R . . C3 C 1.0038(3) 0.11752(14) 0.39571(17) 0.0270(6) Uani 1 1 d . . . H3A H 1.1046 0.1124 0.4050 0.032 Uiso 1 1 calc R . . H3B H 0.9608 0.1182 0.4510 0.032 Uiso 1 1 calc R . . C4 C 0.9475(3) 0.06555(14) 0.34605(18) 0.0275(6) Uani 1 1 d . . . H4A H 0.9694 0.0278 0.3759 0.033 Uiso 1 1 calc R . . H4B H 0.8457 0.0690 0.3398 0.033 Uiso 1 1 calc R . . C5 C 0.6586(3) 0.12440(14) -0.06340(17) 0.0241(6) Uani 1 1 d . . . C6 C 0.7269(3) 0.10612(14) -0.1320(2) 0.0299(7) Uani 1 1 d . . . H6 H 0.8152 0.0877 -0.1264 0.036 Uiso 1 1 calc R . . C7 C 0.6637(3) 0.11514(15) -0.2110(2) 0.0339(7) Uani 1 1 d . . . H7 H 0.7100 0.1031 -0.2597 0.041 Uiso 1 1 calc R . . C8 C 0.5362(3) 0.14098(15) -0.21865(19) 0.0306(7) Uani 1 1 d . . . H8 H 0.4933 0.1463 -0.2723 0.037 Uiso 1 1 calc R . . C9 C 0.4704(3) 0.1592(2) -0.1484(2) 0.0465(10) Uani 1 1 d . . . H9 H 0.3821 0.1775 -0.1539 0.056 Uiso 1 1 calc R . . C10 C 0.5310(3) 0.1512(2) -0.0688(2) 0.0473(10) Uani 1 1 d . . . H10 H 0.4856 0.1638 -0.0202 0.057 Uiso 1 1 calc R . . C11 C 0.5927(3) 0.28774(14) 0.3817(2) 0.0320(7) Uani 1 1 d . . . H11A H 0.6854 0.2711 0.3919 0.048 Uiso 1 1 calc R . . H11B H 0.5449 0.2902 0.4347 0.048 Uiso 1 1 calc R . . H11C H 0.6001 0.3278 0.3576 0.048 Uiso 1 1 calc R . . C12 C 0.5790(3) 0.24467(14) 0.24109(17) 0.0247(6) Uani 1 1 d . . . H12A H 0.6704 0.2252 0.2482 0.030 Uiso 1 1 calc R . . H12B H 0.5939 0.2854 0.2191 0.030 Uiso 1 1 calc R . . C13 C 0.4907(3) 0.20945(13) 0.17855(17) 0.0238(6) Uani 1 1 d . . . H13A H 0.4017 0.2304 0.1683 0.029 Uiso 1 1 calc R . . H13B H 0.5384 0.2070 0.1249 0.029 Uiso 1 1 calc R . . C14 C 0.4632(3) 0.14700(13) 0.21025(17) 0.0242(6) Uani 1 1 d . . . H14A H 0.4098 0.1244 0.1670 0.029 Uiso 1 1 calc R . . H14B H 0.5522 0.1261 0.2207 0.029 Uiso 1 1 calc R . . C15 C 0.1578(3) 0.15689(13) 0.63225(16) 0.0196(5) Uani 1 1 d . . . C16 C 0.1830(3) 0.10037(13) 0.66344(19) 0.0264(6) Uani 1 1 d . . . H16 H 0.2268 0.0710 0.6306 0.032 Uiso 1 1 calc R . . C17 C 0.1430(3) 0.08728(16) 0.7437(2) 0.0339(7) Uani 1 1 d . . . H17 H 0.1606 0.0488 0.7667 0.041 Uiso 1 1 calc R . . C18 C 0.0779(3) 0.13001(16) 0.7899(2) 0.0322(7) Uani 1 1 d . . . H18 H 0.0503 0.1208 0.8448 0.039 Uiso 1 1 calc R . . C19 C 0.0521(3) 0.18627(16) 0.75713(19) 0.0320(7) Uani 1 1 d . . . H19 H 0.0062 0.2153 0.7895 0.038 Uiso 1 1 calc R . . C20 C 0.0930(3) 0.20065(14) 0.67734(19) 0.0267(6) Uani 1 1 d . . . H20 H 0.0769 0.2393 0.6545 0.032 Uiso 1 1 calc R . . C21 C -0.2579(3) 0.27893(15) 0.7235(2) 0.0377(8) Uani 1 1 d . . . H21A H -0.2682 0.2429 0.7575 0.057 Uiso 1 1 calc R . . H21B H -0.2025 0.2696 0.6751 0.057 Uiso 1 1 calc R . . H21C H -0.3493 0.2931 0.7044 0.057 Uiso 1 1 calc R . . C22 C -0.2659(3) 0.34019(15) 0.84943(19) 0.0312(7) Uani 1 1 d . . . H22A H -0.2839 0.3029 0.8805 0.037 Uiso 1 1 calc R . . H22B H -0.3563 0.3578 0.8323 0.037 Uiso 1 1 calc R . . C23 C -0.1885(3) 0.38359(17) 0.90667(19) 0.0350(7) Uani 1 1 d . . . H23A H -0.2457 0.3926 0.9552 0.042 Uiso 1 1 calc R . . H23B H -0.1020 0.3646 0.9279 0.042 Uiso 1 1 calc R . . C24 C -0.1540(3) 0.44108(15) 0.86299(19) 0.0320(7) Uani 1 1 d . . . H24A H -0.2406 0.4614 0.8447 0.038 Uiso 1 1 calc R . . H24B H -0.1036 0.4678 0.9027 0.038 Uiso 1 1 calc R . . C25 C 0.1501(3) 0.40836(14) 0.45109(17) 0.0234(6) Uani 1 1 d . . . C26 C 0.2339(3) 0.36701(15) 0.4137(2) 0.0299(7) Uani 1 1 d . . . H26 H 0.2645 0.3323 0.4431 0.036 Uiso 1 1 calc R . . C27 C 0.2725(3) 0.37736(18) 0.3318(2) 0.0390(8) Uani 1 1 d . . . H27 H 0.3298 0.3495 0.3046 0.047 Uiso 1 1 calc R . . C28 C 0.2272(3) 0.42824(18) 0.2904(2) 0.0397(8) Uani 1 1 d . . . H28 H 0.2547 0.4356 0.2350 0.048 Uiso 1 1 calc R . . C29 C 0.1422(3) 0.46840(17) 0.3292(2) 0.0370(8) Uani 1 1 d . . . H29 H 0.1108 0.5030 0.3000 0.044 Uiso 1 1 calc R . . C30 C 0.1025(3) 0.45881(14) 0.4103(2) 0.0286(7) Uani 1 1 d . . . H30 H 0.0438 0.4863 0.4371 0.034 Uiso 1 1 calc R . . C31 C -0.7287(4) 0.32528(14) 0.8418(2) 0.0368(8) Uani 1 1 d . . . H31A H -0.7692 0.2987 0.7990 0.055 Uiso 1 1 calc R . . H31B H -0.7829 0.3230 0.8924 0.055 Uiso 1 1 calc R . . H31C H -0.6333 0.3129 0.8550 0.055 Uiso 1 1 calc R . . C32 C -0.6628(3) 0.39191(14) 0.72908(18) 0.0267(6) Uani 1 1 d . . . H32A H -0.7039 0.3619 0.6902 0.032 Uiso 1 1 calc R . . H32B H -0.5632 0.3828 0.7368 0.032 Uiso 1 1 calc R . . C33 C -0.6796(3) 0.45382(13) 0.69081(18) 0.0274(6) Uani 1 1 d . . . H33A H -0.6295 0.4555 0.6379 0.033 Uiso 1 1 calc R . . H33B H -0.7786 0.4613 0.6775 0.033 Uiso 1 1 calc R . . C34 C -0.6247(3) 0.50229(14) 0.74925(19) 0.0275(6) Uani 1 1 d . . . H34A H -0.5253 0.4956 0.7624 0.033 Uiso 1 1 calc R . . H34B H -0.6354 0.5419 0.7223 0.033 Uiso 1 1 calc R . . C35 C -0.3684(3) 0.44544(12) 1.14951(18) 0.0209(6) Uani 1 1 d . . . C36 C -0.4378(3) 0.47412(15) 1.21171(19) 0.0289(7) Uani 1 1 d . . . H36 H -0.5183 0.4971 1.1995 0.035 Uiso 1 1 calc R . . C37 C -0.3850(3) 0.46796(16) 1.2934(2) 0.0371(8) Uani 1 1 d . . . H37 H -0.4318 0.4865 1.3377 0.045 Uiso 1 1 calc R . . C38 C -0.2673(3) 0.43586(16) 1.3111(2) 0.0360(8) Uani 1 1 d . . . H38 H -0.2326 0.4327 1.3671 0.043 Uiso 1 1 calc R . . C39 C -0.1986(3) 0.40794(15) 1.2469(2) 0.0332(7) Uani 1 1 d . . . H39 H -0.1167 0.3858 1.2592 0.040 Uiso 1 1 calc R . . C40 C -0.2490(3) 0.41229(14) 1.16494(19) 0.0267(6) Uani 1 1 d . . . H40 H -0.2032 0.3931 1.1207 0.032 Uiso 1 1 calc R . . N1 N 1.1364(2) 0.11838(11) 0.14163(14) 0.0219(5) Uani 1 1 d . . . N2 N 0.9772(2) 0.12917(11) -0.00058(14) 0.0225(5) Uani 1 1 d . . . N3 N 0.8601(2) 0.13058(11) 0.15117(14) 0.0227(5) Uani 1 1 d . . . N4 N 1.0380(3) 0.17802(10) 0.26885(15) 0.0229(5) Uani 1 1 d . . . N5 N 1.0084(3) 0.06457(12) 0.26307(16) 0.0244(5) Uani 1 1 d . . . N6 N 0.5810(2) 0.14959(11) 0.40766(14) 0.0217(5) Uani 1 1 d . . . N7 N 0.4544(2) 0.14067(10) 0.55641(14) 0.0204(5) Uani 1 1 d . . . N8 N 0.3345(2) 0.20439(10) 0.42885(14) 0.0204(5) Uani 1 1 d . . . N9 N 0.5139(2) 0.24877(10) 0.32328(14) 0.0208(5) Uani 1 1 d . . . N10 N 0.3855(3) 0.14838(10) 0.28790(15) 0.0207(5) Uani 1 1 d . . . N11 N -0.2698(2) 0.41557(11) 0.67576(15) 0.0243(5) Uani 1 1 d . . . N12 N -0.1439(2) 0.42245(12) 0.52784(15) 0.0291(6) Uani 1 1 d . . . N13 N -0.0193(2) 0.36310(10) 0.65827(14) 0.0200(5) Uani 1 1 d . . . N14 N -0.1886(2) 0.32561(10) 0.77379(15) 0.0232(5) Uani 1 1 d . . . N15 N -0.0679(2) 0.43035(11) 0.78926(15) 0.0214(5) Uani 1 1 d . . . N16 N -0.8340(2) 0.43962(11) 0.94062(15) 0.0236(5) Uani 1 1 d . . . N17 N -0.6751(2) 0.42946(11) 1.08317(14) 0.0226(5) Uani 1 1 d . . . N18 N -0.5563(2) 0.42949(11) 0.93206(14) 0.0205(5) Uani 1 1 d . . . N19 N -0.7296(2) 0.38739(10) 0.81028(15) 0.0231(5) Uani 1 1 d . . . N20 N -0.7029(3) 0.50043(11) 0.82617(16) 0.0235(5) Uani 1 1 d . . . O1 O 0.7145(2) 0.11326(10) 0.01851(13) 0.0295(5) Uani 1 1 d . . . O2 O 0.19384(19) 0.17000(9) 0.54927(11) 0.0205(4) Uani 1 1 d . . . O3 O 0.11748(19) 0.39853(9) 0.53549(12) 0.0224(4) Uani 1 1 d . . . O4 O -0.41460(18) 0.45181(9) 1.06468(12) 0.0218(4) Uani 1 1 d . . . P1 P 1.00726(7) 0.12249(3) 0.20225(4) 0.01812(14) Uani 1 1 d . . . P2 P 1.12401(7) 0.12747(3) 0.04479(4) 0.01924(14) Uani 1 1 d . . . P3 P 0.84934(7) 0.14462(3) 0.05508(5) 0.02022(15) Uani 1 1 d . . . P4 P 0.45333(7) 0.18707(3) 0.36544(4) 0.01698(13) Uani 1 1 d . . . P5 P 0.58599(7) 0.13047(3) 0.50138(4) 0.01767(14) Uani 1 1 d . . . P6 P 0.34394(7) 0.18836(3) 0.52376(4) 0.01728(13) Uani 1 1 d . . . P7 P -0.13612(7) 0.38373(3) 0.71996(4) 0.01696(13) Uani 1 1 d . . . P8 P -0.27171(7) 0.43653(3) 0.58336(5) 0.01992(14) Uani 1 1 d . . . P9 P -0.02904(7) 0.37723(3) 0.56218(4) 0.01886(14) Uani 1 1 d . . . P10 P -0.70224(7) 0.43953(3) 0.88157(4) 0.01854(14) Uani 1 1 d . . . P11 P -0.82159(7) 0.42745(3) 1.03677(5) 0.02030(15) Uani 1 1 d . . . P12 P -0.54455(7) 0.41725(3) 1.02761(4) 0.01813(14) Uani 1 1 d . . . Cl1 Cl 1.22373(7) 0.20355(3) 0.01391(5) 0.02632(15) Uani 1 1 d . . . Cl2 Cl 1.23951(8) 0.06612(3) -0.01038(5) 0.02872(15) Uani 1 1 d . . . Cl3 Cl 0.80569(8) 0.23256(3) 0.03532(5) 0.03074(16) Uani 1 1 d . . . Cl4 Cl 0.64096(7) 0.04458(3) 0.51352(5) 0.02806(15) Uani 1 1 d . . . Cl5 Cl 0.75129(7) 0.16906(4) 0.56066(5) 0.03060(16) Uani 1 1 d . . . Cl6 Cl 0.37763(8) 0.26384(3) 0.59191(5) 0.02859(15) Uani 1 1 d . . . Cl7 Cl -0.30683(9) 0.52445(3) 0.57623(7) 0.0454(2) Uani 1 1 d . . . Cl8 Cl -0.44344(7) 0.40523(3) 0.52401(4) 0.02570(15) Uani 1 1 d . . . Cl9 Cl -0.05305(8) 0.30012(4) 0.49776(5) 0.03542(18) Uani 1 1 d . . . Cl10 Cl -0.91046(7) 0.34795(3) 1.06391(5) 0.02924(16) Uani 1 1 d . . . Cl11 Cl -0.94974(7) 0.48219(3) 1.09451(5) 0.02947(16) Uani 1 1 d . . . Cl12 Cl -0.48901(7) 0.33057(3) 1.04687(5) 0.02810(15) Uani 1 1 d . . . H20N H -0.729(4) 0.5292(17) 0.851(2) 0.035(10) Uiso 1 1 d . . . H5N H 1.013(3) 0.0324(15) 0.245(2) 0.022(9) Uiso 1 1 d . . . H15N H 0.010(3) 0.4177(14) 0.800(2) 0.025(9) Uiso 1 1 d . . . H10N H 0.304(4) 0.1545(14) 0.281(2) 0.027(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 0.0446(19) 0.0192(15) 0.0378(19) 0.0008(13) 0.0009(15) -0.0017(13) C2 0.0278(14) 0.0344(17) 0.0210(15) -0.0073(13) 0.0010(12) 0.0033(12) C3 0.0289(14) 0.0378(17) 0.0143(14) -0.0012(12) 0.0019(11) 0.0031(13) C4 0.0319(15) 0.0311(16) 0.0196(15) 0.0024(12) 0.0032(12) -0.0060(13) C5 0.0186(12) 0.0359(16) 0.0175(13) 0.0055(12) -0.0035(10) -0.0102(11) C6 0.0275(15) 0.0309(16) 0.0311(17) -0.0028(13) -0.0035(12) 0.0048(12) C7 0.0376(17) 0.0415(19) 0.0227(16) -0.0051(14) 0.0015(13) 0.0008(14) C8 0.0310(15) 0.0412(18) 0.0191(15) 0.0030(13) -0.0066(12) -0.0036(13) C9 0.0241(15) 0.082(3) 0.0327(19) -0.0054(18) -0.0075(14) 0.0126(17) C10 0.0245(16) 0.095(3) 0.0225(17) -0.0034(18) 0.0007(13) 0.0045(17) C11 0.0397(17) 0.0283(16) 0.0281(16) -0.0017(13) 0.0015(13) -0.0158(13) C12 0.0234(14) 0.0316(16) 0.0194(14) 0.0042(12) 0.0054(11) -0.0039(11) C13 0.0229(13) 0.0376(17) 0.0111(12) 0.0047(11) 0.0013(10) -0.0013(11) C14 0.0275(14) 0.0309(16) 0.0143(13) -0.0058(11) 0.0010(11) 0.0019(11) C15 0.0143(11) 0.0304(15) 0.0140(13) 0.0011(11) 0.0009(10) -0.0032(10) C16 0.0294(15) 0.0274(15) 0.0228(15) 0.0017(12) 0.0062(12) -0.0002(12) C17 0.0325(17) 0.0379(18) 0.0319(18) 0.0105(14) 0.0087(14) -0.0005(13) C18 0.0281(15) 0.049(2) 0.0193(15) 0.0047(14) 0.0049(12) -0.0037(14) C19 0.0260(15) 0.0461(19) 0.0244(16) -0.0085(14) 0.0072(12) 0.0021(13) C20 0.0204(13) 0.0309(16) 0.0291(16) -0.0001(13) 0.0032(11) 0.0038(12) C21 0.0327(17) 0.0316(17) 0.049(2) -0.0036(16) -0.0001(15) -0.0085(13) C22 0.0256(14) 0.0470(19) 0.0210(15) 0.0094(14) 0.0023(12) -0.0052(13) C23 0.0256(15) 0.065(2) 0.0146(14) -0.0006(15) 0.0022(11) 0.0013(15) C24 0.0260(14) 0.0465(19) 0.0233(16) -0.0132(14) -0.0037(12) 0.0067(14) C25 0.0176(12) 0.0375(16) 0.0150(14) -0.0016(12) -0.0008(10) -0.0069(11) C26 0.0261(14) 0.0393(18) 0.0243(16) 0.0004(13) 0.0028(12) 0.0025(13) C27 0.0261(15) 0.062(2) 0.0289(18) -0.0075(16) 0.0088(13) -0.0044(15) C28 0.0263(15) 0.071(3) 0.0222(16) 0.0035(17) 0.0040(12) -0.0095(16) C29 0.0312(16) 0.052(2) 0.0277(17) 0.0112(15) -0.0041(13) -0.0114(15) C30 0.0226(14) 0.0346(17) 0.0288(16) -0.0006(13) 0.0024(12) -0.0045(12) C31 0.058(2) 0.0206(15) 0.0316(18) -0.0004(13) -0.0049(16) -0.0040(14) C32 0.0282(15) 0.0316(16) 0.0201(15) -0.0046(12) -0.0013(12) 0.0051(12) C33 0.0336(16) 0.0301(16) 0.0185(15) 0.0000(12) 0.0008(12) 0.0014(12) C34 0.0335(15) 0.0251(15) 0.0239(15) 0.0017(12) 0.0011(12) -0.0029(12) C35 0.0175(12) 0.0244(14) 0.0208(14) 0.0029(11) -0.0004(10) -0.0094(10) C36 0.0202(14) 0.0397(18) 0.0268(16) -0.0082(14) 0.0020(12) -0.0039(12) C37 0.0344(17) 0.053(2) 0.0245(16) -0.0109(15) 0.0062(13) -0.0180(15) C38 0.0417(18) 0.047(2) 0.0186(15) 0.0058(14) -0.0056(13) -0.0224(16) C39 0.0293(15) 0.0359(17) 0.0336(18) 0.0071(14) -0.0111(13) -0.0085(13) C40 0.0193(13) 0.0335(16) 0.0272(16) -0.0010(13) -0.0002(11) -0.0029(11) N1 0.0197(11) 0.0274(13) 0.0185(12) -0.0020(10) 0.0001(9) 0.0001(9) N2 0.0205(11) 0.0307(13) 0.0165(11) -0.0003(10) 0.0025(9) -0.0036(10) N3 0.0169(10) 0.0334(13) 0.0178(12) 0.0035(10) 0.0002(9) -0.0019(10) N4 0.0289(12) 0.0194(12) 0.0203(12) -0.0017(9) 0.0008(10) -0.0012(9) N5 0.0384(14) 0.0159(12) 0.0190(13) -0.0028(10) 0.0018(10) -0.0015(10) N6 0.0225(11) 0.0270(13) 0.0157(12) 0.0014(10) 0.0033(9) 0.0041(9) N7 0.0196(11) 0.0258(12) 0.0158(11) 0.0041(9) 0.0008(9) -0.0010(9) N8 0.0196(11) 0.0247(12) 0.0169(11) 0.0031(9) 0.0013(9) 0.0030(9) N9 0.0256(12) 0.0208(12) 0.0160(11) 0.0018(9) 0.0020(9) -0.0044(9) N10 0.0211(11) 0.0237(12) 0.0172(12) 0.0000(9) -0.0004(9) -0.0029(9) N11 0.0218(11) 0.0327(14) 0.0185(12) -0.0011(10) 0.0005(9) 0.0073(10) N12 0.0231(12) 0.0475(16) 0.0168(12) 0.0115(11) 0.0011(9) 0.0037(11) N13 0.0198(11) 0.0252(12) 0.0150(11) 0.0017(9) 0.0005(9) 0.0052(9) N14 0.0234(11) 0.0250(12) 0.0212(12) 0.0014(10) 0.0013(9) -0.0034(9) N15 0.0208(11) 0.0234(12) 0.0199(12) -0.0031(10) 0.0003(9) 0.0026(9) N16 0.0161(10) 0.0322(13) 0.0225(13) 0.0018(10) -0.0008(9) -0.0008(9) N17 0.0173(10) 0.0345(14) 0.0160(11) -0.0021(10) 0.0002(9) -0.0013(10) N18 0.0164(10) 0.0289(13) 0.0163(11) 0.0011(10) 0.0031(8) 0.0015(9) N19 0.0302(12) 0.0182(11) 0.0205(12) -0.0002(10) -0.0037(10) -0.0010(9) N20 0.0333(13) 0.0165(12) 0.0206(13) -0.0014(10) -0.0004(10) 0.0022(10) O1 0.0239(10) 0.0423(12) 0.0221(11) 0.0109(9) -0.0062(8) -0.0125(9) O2 0.0182(9) 0.0296(10) 0.0139(9) 0.0017(8) 0.0021(7) -0.0027(7) O3 0.0201(9) 0.0320(11) 0.0150(10) -0.0015(8) 0.0007(7) -0.0038(8) O4 0.0178(9) 0.0315(11) 0.0159(10) 0.0034(8) -0.0012(7) -0.0045(8) P1 0.0196(3) 0.0199(3) 0.0147(3) -0.0007(3) -0.0003(3) -0.0017(3) P2 0.0177(3) 0.0227(4) 0.0174(3) -0.0008(3) 0.0024(3) -0.0002(3) P3 0.0158(3) 0.0274(4) 0.0174(4) 0.0045(3) 0.0002(3) -0.0027(3) P4 0.0191(3) 0.0184(3) 0.0134(3) 0.0012(3) 0.0002(2) -0.0014(2) P5 0.0174(3) 0.0195(3) 0.0159(3) -0.0002(3) -0.0010(3) -0.0006(3) P6 0.0178(3) 0.0200(3) 0.0140(3) 0.0005(3) 0.0013(2) -0.0011(3) P7 0.0177(3) 0.0196(3) 0.0136(3) -0.0007(3) 0.0003(2) 0.0021(2) P8 0.0184(3) 0.0205(3) 0.0205(4) 0.0019(3) -0.0036(3) 0.0007(3) P9 0.0183(3) 0.0245(4) 0.0138(3) -0.0011(3) 0.0003(3) -0.0017(3) P10 0.0194(3) 0.0190(3) 0.0171(3) 0.0006(3) -0.0018(3) 0.0007(3) P11 0.0160(3) 0.0244(4) 0.0206(4) -0.0011(3) 0.0007(3) 0.0000(3) P12 0.0161(3) 0.0227(4) 0.0156(3) 0.0017(3) -0.0006(2) -0.0008(3) Cl1 0.0225(3) 0.0250(4) 0.0316(4) 0.0010(3) 0.0043(3) -0.0034(3) Cl2 0.0325(4) 0.0262(4) 0.0279(4) -0.0026(3) 0.0078(3) 0.0070(3) Cl3 0.0292(4) 0.0300(4) 0.0330(4) 0.0066(3) -0.0003(3) 0.0049(3) Cl4 0.0308(4) 0.0216(3) 0.0315(4) 0.0022(3) -0.0034(3) 0.0052(3) Cl5 0.0235(3) 0.0411(4) 0.0270(4) -0.0086(3) -0.0027(3) -0.0092(3) Cl6 0.0362(4) 0.0239(3) 0.0259(4) -0.0071(3) 0.0042(3) -0.0048(3) Cl7 0.0376(4) 0.0193(4) 0.0776(7) 0.0054(4) -0.0232(4) -0.0008(3) Cl8 0.0223(3) 0.0296(4) 0.0249(4) -0.0059(3) -0.0046(3) -0.0032(3) Cl9 0.0444(4) 0.0364(4) 0.0259(4) -0.0129(3) 0.0072(3) -0.0151(3) Cl10 0.0275(3) 0.0251(4) 0.0349(4) 0.0047(3) -0.0012(3) -0.0048(3) Cl11 0.0257(3) 0.0294(4) 0.0339(4) -0.0014(3) 0.0085(3) 0.0046(3) Cl12 0.0309(4) 0.0238(3) 0.0293(4) 0.0051(3) -0.0040(3) 0.0018(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 N4 1.465(4) . ? C2 N4 1.477(4) . ? C2 C3 1.503(4) . ? C3 C4 1.501(4) . ? C4 N5 1.471(4) . ? C5 C6 1.363(4) . ? C5 C10 1.373(4) . ? C5 O1 1.425(3) . ? C6 C7 1.403(4) . ? C7 C8 1.365(4) . ? C8 C9 1.373(5) . ? C9 C10 1.396(4) . ? C11 N9 1.474(3) . ? C12 N9 1.480(4) . ? C12 C13 1.517(4) . ? C13 C14 1.513(4) . ? C14 N10 1.474(4) . ? C15 C16 1.379(4) . ? C15 C20 1.379(4) . ? C15 O2 1.416(3) . ? C16 C17 1.385(4) . ? C17 C18 1.375(5) . ? C18 C19 1.384(5) . ? C19 C20 1.387(4) . ? C21 N14 1.468(4) . ? C22 N14 1.481(4) . ? C22 C23 1.517(4) . ? C23 C24 1.507(5) . ? C24 N15 1.486(4) . ? C25 C30 1.377(4) . ? C25 C26 1.380(4) . ? C25 O3 1.415(3) . ? C26 C27 1.394(4) . ? C27 C28 1.382(5) . ? C28 C29 1.380(5) . ? C29 C30 1.382(4) . ? C31 N19 1.479(4) . ? C32 N19 1.474(4) . ? C32 C33 1.521(4) . ? C33 C34 1.517(4) . ? C34 N20 1.467(4) . ? C35 C36 1.378(4) . ? C35 C40 1.389(4) . ? C35 O4 1.423(3) . ? C36 C37 1.395(4) . ? C37 C38 1.369(5) . ? C38 C39 1.390(5) . ? C39 C40 1.389(4) . ? N1 P2 1.565(2) . ? N1 P1 1.610(2) . ? N2 P2 1.576(2) . ? N2 P3 1.587(2) . ? N3 P3 1.570(2) . ? N3 P1 1.630(2) . ? N4 P1 1.658(2) . ? N5 P1 1.621(3) . ? N6 P5 1.560(2) . ? N6 P4 1.623(2) . ? N7 P6 1.588(2) . ? N7 P5 1.589(2) . ? N8 P6 1.561(2) . ? N8 P4 1.606(2) . ? N9 P4 1.653(2) . ? N10 P4 1.634(2) . ? N11 P8 1.552(2) . ? N11 P7 1.620(2) . ? N12 P8 1.578(3) . ? N12 P9 1.589(2) . ? N13 P9 1.571(2) . ? N13 P7 1.594(2) . ? N14 P7 1.650(2) . ? N15 P7 1.646(2) . ? N16 P11 1.564(2) . ? N16 P10 1.612(2) . ? N17 P11 1.580(2) . ? N17 P12 1.593(2) . ? N18 P12 1.555(2) . ? N18 P10 1.621(2) . ? N19 P10 1.648(2) . ? N20 P10 1.626(2) . ? O1 P3 1.578(2) . ? O2 P6 1.5768(19) . ? O3 P9 1.569(2) . ? O4 P12 1.5766(19) . ? P2 Cl2 1.9950(10) . ? P2 Cl1 2.0263(10) . ? P2 P3 2.6974(10) . ? P3 Cl3 2.0355(10) . ? P5 Cl4 2.0021(10) . ? P5 Cl5 2.0275(9) . ? P6 Cl6 2.0315(10) . ? P8 Cl7 1.9993(10) . ? P8 Cl8 2.0142(9) . ? P9 Cl9 2.0198(10) . ? P11 Cl11 1.9922(10) . ? P11 Cl10 2.0292(10) . ? P12 Cl12 2.0336(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 N4 C2 C3 112.1(2) . . ? C4 C3 C2 111.8(2) . . ? N5 C4 C3 109.9(2) . . ? C6 C5 C10 122.6(3) . . ? C6 C5 O1 120.6(3) . . ? C10 C5 O1 116.7(3) . . ? C5 C6 C7 118.3(3) . . ? C8 C7 C6 120.6(3) . . ? C7 C8 C9 119.7(3) . . ? C8 C9 C10 121.1(3) . . ? C5 C10 C9 117.7(3) . . ? N9 C12 C13 111.8(2) . . ? C14 C13 C12 111.1(2) . . ? N10 C14 C13 111.3(2) . . ? C16 C15 C20 122.7(3) . . ? C16 C15 O2 118.9(3) . . ? C20 C15 O2 118.3(2) . . ? C15 C16 C17 118.6(3) . . ? C18 C17 C16 120.0(3) . . ? C17 C18 C19 120.6(3) . . ? C18 C19 C20 120.5(3) . . ? C15 C20 C19 117.7(3) . . ? N14 C22 C23 112.5(2) . . ? C24 C23 C22 112.3(2) . . ? N15 C24 C23 111.7(3) . . ? C30 C25 C26 122.5(3) . . ? C30 C25 O3 120.0(3) . . ? C26 C25 O3 117.5(3) . . ? C25 C26 C27 118.4(3) . . ? C28 C27 C26 119.8(3) . . ? C29 C28 C27 120.4(3) . . ? C28 C29 C30 120.7(3) . . ? C25 C30 C29 118.3(3) . . ? N19 C32 C33 112.0(2) . . ? C34 C33 C32 111.8(2) . . ? N20 C34 C33 108.5(2) . . ? C36 C35 C40 122.9(3) . . ? C36 C35 O4 119.8(3) . . ? C40 C35 O4 117.2(3) . . ? C35 C36 C37 117.3(3) . . ? C38 C37 C36 121.6(3) . . ? C37 C38 C39 119.8(3) . . ? C40 C39 C38 120.3(3) . . ? C39 C40 C35 118.1(3) . . ? P2 N1 P1 123.63(14) . . ? P2 N2 P3 117.05(15) . . ? P3 N3 P1 122.89(15) . . ? C1 N4 C2 113.5(2) . . ? C1 N4 P1 115.7(2) . . ? C2 N4 P1 119.09(19) . . ? C4 N5 P1 122.4(2) . . ? P5 N6 P4 122.84(15) . . ? P6 N7 P5 117.25(14) . . ? P6 N8 P4 122.64(14) . . ? C11 N9 C12 112.0(2) . . ? C11 N9 P4 114.71(19) . . ? C12 N9 P4 118.58(19) . . ? C14 N10 P4 116.66(19) . . ? P8 N11 P7 122.32(15) . . ? P8 N12 P9 119.02(15) . . ? P9 N13 P7 121.85(14) . . ? C21 N14 C22 111.8(2) . . ? C21 N14 P7 114.7(2) . . ? C22 N14 P7 115.2(2) . . ? C24 N15 P7 114.50(19) . . ? P11 N16 P10 122.69(14) . . ? P11 N17 P12 116.68(14) . . ? P12 N18 P10 123.40(14) . . ? C32 N19 C31 111.6(2) . . ? C32 N19 P10 119.8(2) . . ? C31 N19 P10 115.5(2) . . ? C34 N20 P10 119.3(2) . . ? C5 O1 P3 123.32(17) . . ? C15 O2 P6 123.69(16) . . ? C25 O3 P9 122.62(16) . . ? C35 O4 P12 122.19(16) . . ? N1 P1 N5 109.04(13) . . ? N1 P1 N3 112.78(12) . . ? N5 P1 N3 112.27(13) . . ? N1 P1 N4 107.67(13) . . ? N5 P1 N4 102.43(13) . . ? N3 P1 N4 112.05(13) . . ? N1 P2 N2 119.95(12) . . ? N1 P2 Cl2 108.86(10) . . ? N2 P2 Cl2 108.82(10) . . ? N1 P2 Cl1 109.22(9) . . ? N2 P2 Cl1 107.28(10) . . ? Cl2 P2 Cl1 101.06(4) . . ? N1 P2 P3 90.12(9) . . ? N2 P2 P3 31.60(9) . . ? Cl2 P2 P3 133.85(4) . . ? Cl1 P2 P3 111.96(4) . . ? N3 P3 O1 107.62(12) . . ? N3 P3 N2 118.59(12) . . ? O1 P3 N2 110.22(12) . . ? N3 P3 Cl3 110.64(10) . . ? O1 P3 Cl3 101.95(9) . . ? N2 P3 Cl3 106.57(10) . . ? N3 P3 P2 89.83(9) . . ? O1 P3 P2 136.02(10) . . ? N2 P3 P2 31.36(8) . . ? Cl3 P3 P2 109.16(4) . . ? N8 P4 N6 114.37(12) . . ? N8 P4 N10 109.26(12) . . ? N6 P4 N10 108.94(13) . . ? N8 P4 N9 109.11(12) . . ? N6 P4 N9 109.06(12) . . ? N10 P4 N9 105.75(12) . . ? N6 P5 N7 119.57(12) . . ? N6 P5 Cl4 110.90(10) . . ? N7 P5 Cl4 107.43(9) . . ? N6 P5 Cl5 109.47(10) . . ? N7 P5 Cl5 108.31(9) . . ? Cl4 P5 Cl5 99.21(4) . . ? N8 P6 O2 106.66(11) . . ? N8 P6 N7 119.51(12) . . ? O2 P6 N7 110.88(12) . . ? N8 P6 Cl6 109.58(9) . . ? O2 P6 Cl6 102.18(8) . . ? N7 P6 Cl6 106.69(9) . . ? N13 P7 N11 115.43(12) . . ? N13 P7 N15 108.92(12) . . ? N11 P7 N15 108.27(13) . . ? N13 P7 N14 109.39(12) . . ? N11 P7 N14 108.66(13) . . ? N15 P7 N14 105.74(12) . . ? N11 P8 N12 119.41(13) . . ? N11 P8 Cl7 110.41(10) . . ? N12 P8 Cl7 107.41(11) . . ? N11 P8 Cl8 109.23(10) . . ? N12 P8 Cl8 108.37(10) . . ? Cl7 P8 Cl8 100.31(4) . . ? O3 P9 N13 107.57(11) . . ? O3 P9 N12 109.96(12) . . ? N13 P9 N12 119.10(13) . . ? O3 P9 Cl9 102.16(8) . . ? N13 P9 Cl9 109.30(10) . . ? N12 P9 Cl9 107.43(11) . . ? N16 P10 N18 113.64(12) . . ? N16 P10 N20 109.26(13) . . ? N18 P10 N20 112.11(13) . . ? N16 P10 N19 107.15(13) . . ? N18 P10 N19 111.43(12) . . ? N20 P10 N19 102.58(13) . . ? N16 P11 N17 119.80(13) . . ? N16 P11 Cl11 108.70(10) . . ? N17 P11 Cl11 109.10(10) . . ? N16 P11 Cl10 110.11(10) . . ? N17 P11 Cl10 107.73(10) . . ? Cl11 P11 Cl10 99.49(4) . . ? N18 P12 O4 108.45(12) . . ? N18 P12 N17 119.01(12) . . ? O4 P12 N17 110.11(12) . . ? N18 P12 Cl12 109.14(10) . . ? O4 P12 Cl12 101.94(8) . . ? N17 P12 Cl12 106.84(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.325 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.061 # Attachment '6a.cif' data_2005src1318 _database_code_depnum_ccdc_archive 'CCDC 809131' #TrackingRef '6a.cif' _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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 16.7876(4) _cell_length_b 8.92210(10) _cell_length_c 8.7848(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1315.79(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1748 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8667 _exptl_absorpt_correction_T_max 0.9793 _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 19401 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3018 _reflns_number_gt 2829 _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^)+(0.0832P)^2^+3.7867P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(18) _refine_ls_number_reflns 3018 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.024 _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 Cl1 Cl 0.79984(11) -0.0769(2) 0.7293(3) 0.0716(6) Uani 1 1 d . . . Cl2 Cl 0.97173(12) -0.05535(16) 1.16677(17) 0.0507(4) Uani 1 1 d . . . Cl3 Cl 1.09653(9) 0.1424(2) 1.0019(2) 0.0525(4) Uani 1 1 d . . . P1 P 0.86651(7) 0.32436(14) 0.94145(14) 0.0253(3) Uani 1 1 d . . . P2 P 0.88367(8) 0.08129(17) 0.74654(16) 0.0354(3) Uani 1 1 d . . . P3 P 0.97690(8) 0.09820(13) 1.00102(15) 0.0288(3) Uani 1 1 d . . . O1 O 0.7900(2) 0.3546(4) 1.0391(4) 0.0324(8) Uani 1 1 d . . . O2 O 0.9167(3) 0.0920(7) 0.5697(7) 0.0598(14) Uani 1 1 d . . . N1 N 0.8434(3) 0.2293(6) 0.7947(5) 0.0414(11) Uani 1 1 d . . . N2 N 0.9556(3) 0.0197(5) 0.8430(5) 0.0356(10) Uani 1 1 d . . . N3 N 0.9313(3) 0.2417(5) 1.0483(5) 0.0309(9) Uani 1 1 d . . . N4 N 0.8935(3) 0.4927(5) 0.8891(5) 0.0299(9) Uani 1 1 d . . . C1 C 0.7939(3) 0.4689(7) 1.1578(7) 0.0379(13) Uani 1 1 d . . . H1A H 0.8353 0.4420 1.2333 0.046 Uiso 1 1 calc R . . H1B H 0.7421 0.4756 1.2112 0.046 Uiso 1 1 calc R . . C2 C 0.8141(4) 0.6200(6) 1.0842(7) 0.0391(12) Uani 1 1 d . . . H2A H 0.8155 0.6988 1.1635 0.047 Uiso 1 1 calc R . . H2B H 0.7720 0.6468 1.0101 0.047 Uiso 1 1 calc R . . C3 C 0.8950(3) 0.6136(6) 1.0027(7) 0.0340(11) Uani 1 1 d . . . H3A H 0.9058 0.7106 0.9520 0.041 Uiso 1 1 calc R . . H3B H 0.9379 0.5948 1.0776 0.041 Uiso 1 1 calc R . . C4 C 0.8824(7) 0.1475(14) 0.4815(15) 0.103(4) Uani 1 1 d . . . H4A H 0.8766 0.2539 0.5068 0.154 Uiso 1 1 calc R . . H4B H 0.8296 0.1012 0.4743 0.154 Uiso 1 1 calc R . . H4C H 0.9100 0.1376 0.3837 0.154 Uiso 1 1 calc R . . H4N H 0.935(4) 0.527(7) 0.828(7) 0.027(14) 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 Cl1 0.0525(10) 0.0547(10) 0.1076(17) -0.0268(11) 0.0049(10) -0.0184(8) Cl2 0.0843(12) 0.0298(6) 0.0380(7) 0.0038(6) 0.0012(8) 0.0005(7) Cl3 0.0383(7) 0.0648(10) 0.0545(9) -0.0024(8) -0.0007(7) 0.0030(7) P1 0.0238(5) 0.0269(6) 0.0252(5) -0.0029(5) 0.0008(4) 0.0021(5) P2 0.0377(7) 0.0386(7) 0.0299(6) -0.0117(6) -0.0013(6) -0.0022(6) P3 0.0311(6) 0.0249(5) 0.0303(6) -0.0021(5) -0.0007(5) 0.0054(5) O1 0.0231(16) 0.0353(19) 0.039(2) -0.0015(16) 0.0070(14) 0.0013(13) O2 0.047(3) 0.078(4) 0.054(3) -0.025(3) 0.024(2) 0.006(3) N1 0.050(3) 0.046(3) 0.028(2) -0.009(2) -0.010(2) -0.005(2) N2 0.038(3) 0.034(2) 0.035(2) -0.0094(19) 0.006(2) 0.0029(19) N3 0.030(2) 0.028(2) 0.035(2) -0.0069(18) -0.0049(17) 0.0068(16) N4 0.030(2) 0.032(2) 0.027(2) 0.0005(17) 0.0016(17) 0.0034(17) C1 0.031(3) 0.052(3) 0.031(3) -0.010(2) 0.008(2) 0.010(2) C2 0.039(3) 0.034(3) 0.044(3) -0.003(2) 0.007(2) 0.010(2) C3 0.036(3) 0.029(2) 0.037(3) 0.001(2) 0.005(2) 0.0021(19) C4 0.082(7) 0.104(8) 0.121(10) -0.026(8) 0.072(8) 0.008(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 Cl1 P2 1.999(2) . ? Cl2 P3 2.001(2) . ? Cl3 P3 2.047(2) . ? P1 O1 1.568(4) . ? P1 N1 1.591(5) . ? P1 N3 1.615(4) . ? P1 N4 1.635(5) . ? P2 N1 1.543(6) . ? P2 N2 1.575(5) . ? P2 O2 1.653(6) . ? P3 N3 1.549(4) . ? P3 N2 1.595(5) . ? O1 C1 1.460(7) . ? O2 C4 1.085(14) . ? N4 C3 1.469(7) . ? N4 H4N 0.92(6) . ? C1 C2 1.533(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.537(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? 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 P1 N1 109.6(3) . . ? O1 P1 N3 108.2(2) . . ? N1 P1 N3 113.1(3) . . ? O1 P1 N4 102.9(2) . . ? N1 P1 N4 109.2(3) . . ? N3 P1 N4 113.4(2) . . ? N1 P2 N2 119.2(2) . . ? N1 P2 O2 110.8(3) . . ? N2 P2 O2 105.6(3) . . ? N1 P2 Cl1 108.5(2) . . ? N2 P2 Cl1 109.5(2) . . ? O2 P2 Cl1 101.9(2) . . ? N3 P3 N2 119.1(2) . . ? N3 P3 Cl2 110.44(19) . . ? N2 P3 Cl2 108.83(19) . . ? N3 P3 Cl3 108.95(18) . . ? N2 P3 Cl3 107.89(19) . . ? Cl2 P3 Cl3 99.90(9) . . ? C1 O1 P1 118.3(3) . . ? C4 O2 P2 121.3(6) . . ? P2 N1 P1 124.8(3) . . ? P2 N2 P3 119.1(3) . . ? P3 N3 P1 123.7(3) . . ? C3 N4 P1 119.2(3) . . ? C3 N4 H4N 98(4) . . ? P1 N4 H4N 132(4) . . ? O1 C1 C2 108.8(4) . . ? O1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? O1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C1 C2 C3 111.0(4) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N4 C3 C2 109.2(4) . . ? N4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? N4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.294 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.116 # Attachment '8a.cif' data_8a _database_code_depnum_ccdc_archive 'CCDC 809132' #TrackingRef '8a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl3 N4 O2 P3' _chemical_formula_weight 407.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pbca 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' '-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 11.6597(17) _cell_length_b 8.0541(10) _cell_length_c 35.094(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3295.6(8) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2479 _cell_measurement_theta_min 2.9050 _cell_measurement_theta_max 26.1831 _cell_measurement_temperature 296.0(2) _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 296.0(2) _diffrn_source ImuS _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type Apex2 _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10456 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 33 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2907 _reflns_number_gt 2020 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.0918 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_number_reflns 2907 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.4545P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.285 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_data_collection ? _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P P1 0.58426(8) -0.06387(10) 0.36631(2) 0.0377(2) Uani d . 1 . . P P2 0.56800(7) 0.17407(10) 0.30899(2) 0.0330(2) Uani d . 1 . . P P3 0.45135(8) 0.21056(10) 0.37709(2) 0.0390(2) Uani d . 1 . . N N1 0.6099(2) -0.0050(3) 0.32467(7) 0.0431(7) Uani d . 1 . . N N2 0.4984(2) 0.2835(3) 0.33869(7) 0.0434(7) Uani d . 1 . . N N3 0.4998(3) 0.0394(3) 0.39196(8) 0.0524(8) Uani d . 1 . . N N4 0.6725(2) 0.2824(3) 0.29118(8) 0.0424(7) Uani d . 1 . . H H4 0.716(3) 0.325(4) 0.3054(10) 0.064 Uiso d . 1 . . O O1 0.48966(16) 0.1434(3) 0.27322(6) 0.0377(5) Uani d . 1 . . O O2 0.4669(2) 0.3506(3) 0.40774(6) 0.0461(6) Uani d . 1 . . Cl Cl1 0.53282(8) -0.29977(10) 0.36547(3) 0.0528(3) Uani d . 1 . . Cl Cl2 0.73424(8) -0.08947(12) 0.39439(3) 0.0609(3) Uani d . 1 . . Cl Cl3 0.28004(8) 0.18809(14) 0.37414(3) 0.0692(3) Uani d . 1 . . C C1 0.5409(3) 0.0874(4) 0.23783(9) 0.0466(9) Uani d . 1 . . H H1A 0.4827 0.0836 0.2181 0.056 Uiso calc R 1 . . H H1B 0.5707 -0.0241 0.2412 0.056 Uiso calc R 1 . . C C2 0.6359(3) 0.1999(5) 0.22552(10) 0.0535(10) Uani d . 1 . . H H2A 0.6044 0.3081 0.2194 0.064 Uiso calc R 1 . . H H2B 0.6711 0.1555 0.2027 0.064 Uiso calc R 1 . . C C3 0.7257(3) 0.2193(4) 0.25584(10) 0.0499(9) Uani d . 1 . . H H3A 0.7618 0.1129 0.2607 0.06 Uiso calc R 1 . . H H3B 0.7843 0.2961 0.2472 0.06 Uiso calc R 1 . . C C4 0.4302(3) 0.3370(4) 0.44636(9) 0.0446(9) Uani d . 1 . . C C5 0.4950(4) 0.2503(5) 0.47134(11) 0.0700(12) Uani d . 1 . . H H5 0.5602 0.194 0.4633 0.084 Uiso calc R 1 . . C C6 0.4615(5) 0.2474(6) 0.50949(13) 0.0905(16) Uani d . 1 . . H H6 0.5038 0.1866 0.5271 0.109 Uiso calc R 1 . . C C7 0.3678(6) 0.3329(6) 0.52087(13) 0.0876(17) Uani d . 1 . . H H7 0.3468 0.3328 0.5464 0.105 Uiso calc R 1 . . C C8 0.3045(5) 0.4184(6) 0.49528(14) 0.0904(16) Uani d . 1 . . H H8 0.2397 0.4759 0.5033 0.109 Uiso calc R 1 . . C C9 0.3352(4) 0.4211(5) 0.45709(11) 0.0715(12) Uani d . 1 . . H H9 0.2917 0.4793 0.4393 0.086 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 0.0488(5) 0.0312(4) 0.0330(5) 0.0031(4) 0.0002(4) 0.0062(4) P2 0.0369(5) 0.0322(4) 0.0299(4) 0.0011(4) 0.0017(4) 0.0052(4) P3 0.0492(5) 0.0339(5) 0.0339(5) 0.0029(4) 0.0069(4) 0.0017(4) N1 0.0619(18) 0.0361(15) 0.0312(15) 0.0157(14) 0.0083(13) 0.0060(13) N2 0.0631(19) 0.0325(14) 0.0347(15) 0.0109(14) 0.0140(14) 0.0061(12) N3 0.079(2) 0.0402(16) 0.0375(17) 0.0124(15) 0.0179(15) 0.0108(14) N4 0.0418(18) 0.0434(17) 0.0419(18) -0.0117(14) -0.0017(14) -0.0015(14) O1 0.0310(12) 0.0460(13) 0.0361(13) -0.0015(10) 0.0000(10) 0.0013(11) O2 0.0635(16) 0.0380(12) 0.0366(13) -0.0071(11) 0.0111(11) -0.0029(11) Cl1 0.0613(6) 0.0344(5) 0.0626(6) -0.0060(4) -0.0077(5) 0.0057(4) Cl2 0.0578(6) 0.0659(6) 0.0591(6) -0.0106(5) -0.0189(5) 0.0131(5) Cl3 0.0506(6) 0.0941(8) 0.0629(7) -0.0080(5) 0.0003(5) 0.0005(6) C1 0.044(2) 0.056(2) 0.040(2) 0.0048(18) -0.0018(16) -0.0106(18) C2 0.063(2) 0.060(2) 0.038(2) 0.007(2) 0.0145(19) 0.0032(18) C3 0.036(2) 0.049(2) 0.064(3) -0.0080(17) 0.0166(18) 0.0019(19) C4 0.060(2) 0.0382(19) 0.035(2) -0.0077(18) 0.0057(18) -0.0002(16) C5 0.084(3) 0.078(3) 0.048(3) 0.011(3) -0.010(2) -0.005(2) C6 0.143(5) 0.082(3) 0.047(3) 0.002(3) -0.015(3) 0.003(2) C7 0.153(5) 0.063(3) 0.047(3) -0.019(3) 0.027(3) -0.006(2) C8 0.115(4) 0.080(3) 0.076(4) 0.007(3) 0.041(3) -0.016(3) C9 0.095(3) 0.069(3) 0.051(3) 0.022(3) 0.017(2) 0.000(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 N1 . 1.565(3) ? P1 N3 . 1.573(3) ? P1 Cl1 . 1.9926(12) ? P1 Cl2 . 2.0179(12) ? P2 O1 . 1.572(2) ? P2 N2 . 1.588(3) ? P2 N1 . 1.619(3) ? P2 N4 . 1.624(3) ? P3 O2 . 1.569(2) ? P3 N2 . 1.569(3) ? P3 N3 . 1.578(3) ? P3 Cl3 . 2.0082(14) ? N4 C3 . 1.477(4) ? N4 H4 . 0.79(3) ? O1 C1 . 1.451(3) ? O2 C4 . 1.426(4) ? C1 C2 . 1.495(5) ? C1 H1A . 0.97 ? C1 H1B . 0.97 ? C2 C3 . 1.501(5) ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 H3A . 0.97 ? C3 H3B . 0.97 ? C4 C9 . 1.352(5) ? C4 C5 . 1.352(5) ? C5 C6 . 1.394(6) ? C5 H5 . 0.93 ? C6 C7 . 1.352(7) ? C6 H6 . 0.93 ? C7 C8 . 1.351(7) ? C7 H7 . 0.93 ? C8 C9 . 1.388(5) ? C8 H8 . 0.93 ? C9 H9 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 P1 N3 . . 119.61(14) ? N1 P1 Cl1 . . 109.43(11) ? N3 P1 Cl1 . . 108.92(12) ? N1 P1 Cl2 . . 108.75(11) ? N3 P1 Cl2 . . 108.50(13) ? Cl1 P1 Cl2 . . 99.82(5) ? O1 P2 N2 . . 108.33(14) ? O1 P2 N1 . . 107.86(13) ? N2 P2 N1 . . 115.20(14) ? O1 P2 N4 . . 102.30(13) ? N2 P2 N4 . . 109.75(15) ? N1 P2 N4 . . 112.51(15) ? O2 P3 N2 . . 106.20(13) ? O2 P3 N3 . . 111.10(14) ? N2 P3 N3 . . 119.08(14) ? O2 P3 Cl3 . . 102.41(10) ? N2 P3 Cl3 . . 109.71(12) ? N3 P3 Cl3 . . 107.10(12) ? P1 N1 P2 . . 121.96(16) ? P3 N2 P2 . . 122.29(16) ? P1 N3 P3 . . 119.78(17) ? C3 N4 P2 . . 117.0(2) ? C3 N4 H4 . . 114.(3) ? P2 N4 H4 . . 118.(3) ? C1 O1 P2 . . 119.55(19) ? C4 O2 P3 . . 124.17(19) ? O1 C1 C2 . . 111.3(3) ? O1 C1 H1A . . 109.4 ? C2 C1 H1A . . 109.4 ? O1 C1 H1B . . 109.4 ? C2 C1 H1B . . 109.4 ? H1A C1 H1B . . 108.0 ? C1 C2 C3 . . 112.0(3) ? C1 C2 H2A . . 109.2 ? C3 C2 H2A . . 109.2 ? C1 C2 H2B . . 109.2 ? C3 C2 H2B . . 109.2 ? H2A C2 H2B . . 107.9 ? N4 C3 C2 . . 109.8(3) ? N4 C3 H3A . . 109.7 ? C2 C3 H3A . . 109.7 ? N4 C3 H3B . . 109.7 ? C2 C3 H3B . . 109.7 ? H3A C3 H3B . . 108.2 ? C9 C4 C5 . . 122.4(4) ? C9 C4 O2 . . 118.2(3) ? C5 C4 O2 . . 119.3(3) ? C4 C5 C6 . . 118.4(4) ? C4 C5 H5 . . 120.8 ? C6 C5 H5 . . 120.8 ? C7 C6 C5 . . 120.1(5) ? C7 C6 H6 . . 120.0 ? C5 C6 H6 . . 120.0 ? C8 C7 C6 . . 120.3(5) ? C8 C7 H7 . . 119.8 ? C6 C7 H7 . . 119.8 ? C7 C8 C9 . . 120.6(5) ? C7 C8 H8 . . 119.7 ? C9 C8 H8 . . 119.7 ? C4 C9 C8 . . 118.2(4) ? C4 C9 H9 . . 120.9 ? C8 C9 H9 . . 120.9 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N3 P1 N1 P2 . . . . 9.6(3) ? Cl1 P1 N1 P2 . . . . 136.21(17) ? Cl2 P1 N1 P2 . . . . -115.69(18) ? O1 P2 N1 P1 . . . . -121.73(19) ? N2 P2 N1 P1 . . . . -0.6(3) ? N4 P2 N1 P1 . . . . 126.2(2) ? O2 P3 N2 P2 . . . . 142.2(2) ? N3 P3 N2 P2 . . . . 16.0(3) ? Cl3 P3 N2 P2 . . . . -107.86(19) ? O1 P2 N2 P3 . . . . 108.6(2) ? N1 P2 N2 P3 . . . . -12.3(3) ? N4 P2 N2 P3 . . . . -140.5(2) ? N1 P1 N3 P3 . . . . -6.1(3) ? Cl1 P1 N3 P3 . . . . -132.93(18) ? Cl2 P1 N3 P3 . . . . 119.33(19) ? O2 P3 N3 P1 . . . . -130.1(2) ? N2 P3 N3 P1 . . . . -6.3(3) ? Cl3 P3 N3 P1 . . . . 118.81(19) ? O1 P2 N4 C3 . . . . -48.5(3) ? N2 P2 N4 C3 . . . . -163.3(2) ? N1 P2 N4 C3 . . . . 67.0(3) ? N2 P2 O1 C1 . . . . 163.1(2) ? N1 P2 O1 C1 . . . . -71.6(2) ? N4 P2 O1 C1 . . . . 47.3(3) ? N2 P3 O2 C4 . . . . 177.2(3) ? N3 P3 O2 C4 . . . . -51.9(3) ? Cl3 P3 O2 C4 . . . . 62.2(3) ? P2 O1 C1 C2 . . . . -54.2(3) ? O1 C1 C2 C3 . . . . 55.6(4) ? P2 N4 C3 C2 . . . . 56.7(3) ? C1 C2 C3 N4 . . . . -57.3(4) ? P3 O2 C4 C9 . . . . -105.2(3) ? P3 O2 C4 C5 . . . . 79.1(4) ? C9 C4 C5 C6 . . . . 0.4(6) ? O2 C4 C5 C6 . . . . 175.9(3) ? C4 C5 C6 C7 . . . . -1.4(7) ? C5 C6 C7 C8 . . . . 1.5(8) ? C6 C7 C8 C9 . . . . -0.6(8) ? C5 C4 C9 C8 . . . . 0.4(6) ? O2 C4 C9 C8 . . . . -175.1(4) ? C7 C8 C9 C4 . . . . -0.3(7) ? # Attachment '9a.cif' data_2006src0703 _database_code_depnum_ccdc_archive 'CCDC 809133' #TrackingRef '9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 Cl3 N6 P3' _chemical_formula_weight 397.54 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' 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 6.59760(10) _cell_length_b 9.4568(2) _cell_length_c 26.8820(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1677.23(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2258 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8648 _exptl_absorpt_correction_T_max 0.9917 _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 19743 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3839 _reflns_number_gt 3376 _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^)+(0.0255P)^2^+0.6065P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.41(7) _refine_ls_number_reflns 3839 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 1.3454(4) 0.4891(3) 0.95513(10) 0.0265(6) Uani 1 1 d . . . H1A H 1.3166 0.3878 0.9522 0.040 Uiso 1 1 calc R . . H1B H 1.4764 0.5025 0.9717 0.040 Uiso 1 1 calc R . . H1C H 1.3501 0.5315 0.9219 0.040 Uiso 1 1 calc R . . C2 C 1.1722(4) 0.4931(3) 1.03513(9) 0.0232(6) Uani 1 1 d . . . H2A H 1.3063 0.5003 1.0514 0.028 Uiso 1 1 calc R . . H2B H 1.1386 0.3915 1.0317 0.028 Uiso 1 1 calc R . . C3 C 1.0142(4) 0.5639(3) 1.06776(9) 0.0234(6) Uani 1 1 d . . . H3A H 1.0107 0.5164 1.1006 0.028 Uiso 1 1 calc R . . H3B H 1.0528 0.6639 1.0732 0.028 Uiso 1 1 calc R . . C4 C 0.8056(4) 0.5579(3) 1.04442(9) 0.0205(5) Uani 1 1 d . . . H4A H 0.7644 0.4579 1.0403 0.025 Uiso 1 1 calc R . . H4B H 0.7065 0.6041 1.0668 0.025 Uiso 1 1 calc R . . C5 C 0.8567(4) 0.8971(2) 0.82420(10) 0.0245(6) Uani 1 1 d . . . H5A H 0.9899 0.9294 0.8116 0.029 Uiso 1 1 calc R . . H5B H 0.8387 0.9308 0.8588 0.029 Uiso 1 1 calc R . . C6 C 0.6837(5) 0.9474(3) 0.79065(10) 0.0318(7) Uani 1 1 d . . . H6A H 0.5537 0.9494 0.8090 0.038 Uiso 1 1 calc R . . H6B H 0.7117 1.0431 0.7773 0.038 Uiso 1 1 calc R . . C7 C 0.6782(5) 0.8377(3) 0.74886(10) 0.0314(7) Uani 1 1 d . . . H7A H 0.5364 0.8149 0.7399 0.038 Uiso 1 1 calc R . . H7B H 0.7484 0.8741 0.7189 0.038 Uiso 1 1 calc R . . C8 C 0.7861(5) 0.7065(3) 0.76880(10) 0.0330(7) Uani 1 1 d . . . H8A H 0.6960 0.6228 0.7674 0.040 Uiso 1 1 calc R . . H8B H 0.9103 0.6865 0.7493 0.040 Uiso 1 1 calc R . . N1 N 0.9830(3) 0.6837(2) 0.91038(7) 0.0186(4) Uani 1 1 d . . . N2 N 0.9353(3) 0.4795(2) 0.83912(7) 0.0219(5) Uani 1 1 d . . . N3 N 0.8939(3) 0.41424(19) 0.93717(7) 0.0177(4) Uani 1 1 d . . . N4 N 1.1840(3) 0.5579(2) 0.98474(7) 0.0181(4) Uani 1 1 d . . . N5 N 0.8027(3) 0.6289(2) 0.99555(8) 0.0175(4) Uani 1 1 d . . . N6 N 0.8372(3) 0.7422(2) 0.82101(8) 0.0207(5) Uani 1 1 d . . . P1 P 0.96361(9) 0.57147(6) 0.95441(2) 0.01506(14) Uani 1 1 d . . . P2 P 0.98281(10) 0.63952(7) 0.85368(2) 0.01885(14) Uani 1 1 d . . . P3 P 0.88909(9) 0.36937(6) 0.88160(2) 0.01655(14) Uani 1 1 d . . . Cl1 Cl 1.27149(10) 0.67941(7) 0.82774(3) 0.03088(17) Uani 1 1 d . . . Cl2 Cl 0.62092(9) 0.27741(6) 0.86612(2) 0.02576(15) Uani 1 1 d . . . Cl3 Cl 1.07583(9) 0.20178(6) 0.87105(2) 0.02415(15) Uani 1 1 d . . . H5N H 0.792(4) 0.708(3) 0.9975(11) 0.030(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 0.0183(13) 0.0340(15) 0.0272(15) -0.0023(13) 0.0002(11) 0.0046(11) C2 0.0250(14) 0.0267(14) 0.0178(14) 0.0032(11) -0.0043(10) 0.0033(11) C3 0.0315(15) 0.0237(13) 0.0148(13) 0.0031(11) -0.0013(10) 0.0031(12) C4 0.0267(13) 0.0204(13) 0.0146(13) 0.0008(11) 0.0057(10) 0.0017(11) C5 0.0349(15) 0.0150(13) 0.0236(14) 0.0007(11) 0.0012(12) -0.0022(10) C6 0.0461(18) 0.0265(15) 0.0230(15) 0.0032(13) -0.0023(13) 0.0024(13) C7 0.0476(18) 0.0281(16) 0.0183(14) 0.0020(12) -0.0022(12) 0.0007(13) C8 0.0515(18) 0.0299(15) 0.0176(15) -0.0023(12) -0.0094(13) 0.0008(14) N1 0.0245(11) 0.0152(10) 0.0161(11) -0.0004(8) -0.0002(9) -0.0061(9) N2 0.0364(13) 0.0164(10) 0.0128(11) -0.0016(8) 0.0024(9) -0.0053(9) N3 0.0223(11) 0.0152(10) 0.0157(11) -0.0013(8) -0.0011(9) -0.0036(9) N4 0.0192(11) 0.0190(11) 0.0161(11) -0.0015(9) -0.0004(8) -0.0004(9) N5 0.0253(11) 0.0124(11) 0.0148(11) -0.0003(9) -0.0008(8) 0.0016(9) N6 0.0337(12) 0.0151(10) 0.0133(11) 0.0011(9) -0.0018(9) -0.0052(8) P1 0.0170(3) 0.0141(3) 0.0141(3) -0.0011(2) -0.0006(2) -0.0012(2) P2 0.0258(3) 0.0157(3) 0.0150(3) -0.0001(3) 0.0018(3) -0.0041(3) P3 0.0203(3) 0.0131(3) 0.0163(3) -0.0013(3) -0.0008(3) -0.0027(3) Cl1 0.0307(4) 0.0335(4) 0.0284(4) -0.0013(3) 0.0099(3) -0.0074(3) Cl2 0.0245(3) 0.0267(3) 0.0261(4) -0.0032(3) -0.0045(3) -0.0071(3) Cl3 0.0289(3) 0.0181(3) 0.0255(3) -0.0027(3) 0.0011(3) 0.0026(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 N4 1.480(3) . ? C2 N4 1.489(3) . ? C2 C3 1.518(3) . ? C3 C4 1.514(4) . ? C4 N5 1.475(3) . ? C5 N6 1.474(3) . ? C5 C6 1.530(4) . ? C6 C7 1.530(4) . ? C7 C8 1.528(4) . ? C8 N6 1.482(3) . ? N1 P2 1.580(2) . ? N1 P1 1.595(2) . ? N2 P3 1.575(2) . ? N2 P2 1.595(2) . ? N3 P3 1.553(2) . ? N3 P1 1.6239(19) . ? N4 P1 1.672(2) . ? N5 P1 1.627(2) . ? N6 P2 1.624(2) . ? P2 Cl1 2.0631(9) . ? P3 Cl2 2.0149(9) . ? P3 Cl3 2.0274(9) . ? 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 C2 C3 112.36(19) . . ? C4 C3 C2 111.6(2) . . ? N5 C4 C3 111.3(2) . . ? N6 C5 C6 102.1(2) . . ? C7 C6 C5 103.9(2) . . ? C8 C7 C6 106.4(2) . . ? N6 C8 C7 104.7(2) . . ? P2 N1 P1 122.67(12) . . ? P3 N2 P2 119.17(12) . . ? P3 N3 P1 122.04(12) . . ? C1 N4 C2 110.24(19) . . ? C1 N4 P1 113.40(16) . . ? C2 N4 P1 115.42(16) . . ? C4 N5 P1 116.41(16) . . ? C5 N6 C8 107.5(2) . . ? C5 N6 P2 120.74(17) . . ? C8 N6 P2 120.70(17) . . ? N1 P1 N3 114.84(10) . . ? N1 P1 N5 109.55(11) . . ? N3 P1 N5 108.37(11) . . ? N1 P1 N4 110.06(11) . . ? N3 P1 N4 108.38(10) . . ? N5 P1 N4 105.18(10) . . ? N1 P2 N2 119.20(11) . . ? N1 P2 N6 111.35(11) . . ? N2 P2 N6 108.56(11) . . ? N1 P2 Cl1 106.09(8) . . ? N2 P2 Cl1 105.79(9) . . ? N6 P2 Cl1 104.72(8) . . ? N3 P3 N2 120.85(11) . . ? N3 P3 Cl2 109.55(8) . . ? N2 P3 Cl2 107.79(9) . . ? N3 P3 Cl3 109.61(8) . . ? N2 P3 Cl3 107.31(8) . . ? Cl2 P3 Cl3 99.63(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.272 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.066