Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Simon Coles' _publ_contact_author_email S.J.Coles@soton.ac.uk loop_ _publ_author_name 'S.J. Coles' 'M.B. Hursthouse' 'R.A. Shaw' 'D.B. Davies' 'A. Kilic' 'A. Uslu' data_03HUR510 _database_code_depnum_ccdc_archive 'CCDC 217959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Cl8 N6 O4 P6' _chemical_formula_weight 685.59 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 6.3636(13) _cell_length_b 8.1499(16) _cell_length_c 11.892(2) _cell_angle_alpha 80.21(3) _cell_angle_beta 83.67(3) _cell_angle_gamma 69.27(3) _cell_volume 567.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 21209 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 1.444 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.8126 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\\f and \\w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8742 _diffrn_reflns_av_R_equivalents 0.1016 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2557 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+1.1971P] 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 0.032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2557 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.004 _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 C1 C 0.3672(14) 0.3813(11) 0.9708(7) 0.0346(17) Uani 0.50 1 d P A 1 H1A H 0.4103 0.2656 1.0208 0.041 Uiso 0.50 1 calc PR A 1 H1B H 0.2028 0.4417 0.9814 0.041 Uiso 0.50 1 calc PR A 1 C2 C 0.2461(12) 0.6265(10) 1.0097(6) 0.0299(16) Uani 0.50 1 d P A 1 H2A H 0.1436 0.5634 0.9996 0.036 Uiso 0.50 1 calc PR A 1 H2B H 0.2098 0.6677 1.0854 0.036 Uiso 0.50 1 calc PR A 1 C1' C 0.5781(12) 0.4621(11) 0.8809(6) 0.0317(16) Uani 0.50 1 d P A 2 H1'1 H 0.7401 0.3900 0.8772 0.038 Uiso 0.50 1 calc PR A 2 H1'2 H 0.5542 0.5738 0.8276 0.038 Uiso 0.50 1 calc PR A 2 C2' C 0.4769(13) 0.6595(10) 0.9150(7) 0.0316(16) Uani 0.50 1 d P A 2 H2'1 H 0.5272 0.6255 0.8378 0.038 Uiso 0.50 1 calc PR A 2 H2'2 H 0.5699 0.7247 0.9343 0.038 Uiso 0.50 1 calc PR A 2 C3 C 0.5000 0.5000 1.0000 0.0322(12) Uani 1 2 d S . . N1 N 0.3756(6) 0.5261(4) 0.6435(3) 0.0370(8) Uani 1 1 d . . . N2 N 0.2080(6) 0.8599(4) 0.6970(3) 0.0372(8) Uani 1 1 d . . . N3 N 0.0481(5) 0.6084(4) 0.8101(3) 0.0330(7) Uani 1 1 d . . . O1 O 0.4322(5) 0.3564(4) 0.8488(2) 0.0418(7) Uani 1 1 d . . . O2 O 0.2214(5) 0.7788(4) 0.9178(2) 0.0385(7) Uani 1 1 d . . . P1 P 0.25299(18) 0.46109(13) 0.75581(9) 0.0327(3) Uani 1 1 d . A . P2 P 0.34478(17) 0.72873(14) 0.60944(9) 0.0335(3) Uani 1 1 d . . . P3 P 0.08948(17) 0.78889(13) 0.80933(9) 0.0324(3) Uani 1 1 d . A . Cl1 Cl 0.1516(3) 0.27095(17) 0.72617(11) 0.0621(4) Uani 1 1 d . . . Cl2 Cl 0.6483(2) 0.7507(2) 0.57846(11) 0.0557(4) Uani 1 1 d . . . Cl3 Cl 0.21393(19) 0.81692(15) 0.45731(9) 0.0458(3) Uani 1 1 d . . . Cl4 Cl -0.2032(2) 0.97464(15) 0.83902(10) 0.0585(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(4) 0.035(4) 0.029(4) -0.002(3) -0.005(3) -0.006(3) C2 0.026(4) 0.036(4) 0.025(4) -0.006(3) 0.002(3) -0.007(3) C1' 0.025(4) 0.040(4) 0.027(4) -0.005(3) 0.003(3) -0.007(3) C2' 0.028(4) 0.036(4) 0.030(4) 0.000(3) 0.002(3) -0.014(3) C3 0.026(3) 0.041(3) 0.028(3) -0.006(2) 0.000(2) -0.010(2) N1 0.0422(19) 0.0327(17) 0.0314(18) -0.0101(14) 0.0072(15) -0.0074(15) N2 0.052(2) 0.0302(17) 0.0279(18) -0.0062(14) 0.0014(15) -0.0128(16) N3 0.0297(16) 0.0352(17) 0.0306(17) -0.0086(14) 0.0038(13) -0.0064(14) O1 0.0459(17) 0.0349(15) 0.0334(16) -0.0103(12) -0.0055(13) 0.0032(13) O2 0.0528(18) 0.0297(14) 0.0310(15) -0.0080(11) -0.0053(13) -0.0090(13) P1 0.0390(6) 0.0265(5) 0.0300(6) -0.0082(4) 0.0002(4) -0.0067(4) P2 0.0337(6) 0.0378(6) 0.0264(5) -0.0055(4) 0.0013(4) -0.0095(5) P3 0.0360(6) 0.0273(5) 0.0278(5) -0.0079(4) 0.0013(4) -0.0025(4) Cl1 0.1101(11) 0.0523(7) 0.0424(7) -0.0199(5) 0.0115(7) -0.0489(8) Cl2 0.0403(6) 0.0819(9) 0.0466(7) -0.0013(6) 0.0016(5) -0.0278(6) Cl3 0.0478(6) 0.0508(7) 0.0297(6) -0.0073(4) -0.0053(4) -0.0041(5) Cl4 0.0609(8) 0.0366(6) 0.0483(7) -0.0038(5) 0.0162(6) 0.0129(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.492(8) . ? C1 C3 1.590(8) . ? C1 C2 1.987(11) . ? C2 O2 1.482(8) . ? C2 C3 1.583(7) . ? C1' C3 1.495(7) . ? C1' O1 1.582(9) . ? C2' C3 1.478(8) . ? C2' O2 1.571(8) . ? C3 C2' 1.478(8) 2_667 ? C3 C1' 1.495(7) 2_667 ? C3 C2 1.583(7) 2_667 ? C3 C1 1.590(8) 2_667 ? N1 P2 1.578(4) . ? N1 P1 1.580(4) . ? N2 P2 1.582(3) . ? N2 P3 1.585(4) . ? N3 P3 1.582(4) . ? N3 P1 1.590(3) . ? O1 P1 1.588(3) . ? O2 P3 1.590(3) . ? P1 Cl1 1.9710(16) . ? P1 P3 2.6626(16) . ? P2 Cl3 1.9873(16) . ? P2 Cl2 1.9912(16) . ? P3 Cl4 1.9812(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 105.6(5) . . ? O1 C1 C2 118.4(5) . . ? C3 C1 C2 51.1(3) . . ? O2 C2 C3 106.5(5) . . ? O2 C2 C1 119.7(5) . . ? C3 C2 C1 51.4(3) . . ? C3 C1' O1 105.9(5) . . ? C3 C2' O2 107.3(5) . . ? C2' C3 C2' 180.000(2) 2_667 . ? C2' C3 C1' 114.3(4) 2_667 . ? C2' C3 C1' 65.7(4) . . ? C2' C3 C1' 65.7(4) 2_667 2_667 ? C2' C3 C1' 114.3(4) . 2_667 ? C1' C3 C1' 180.000(3) . 2_667 ? C2' C3 C2 107.2(4) 2_667 . ? C2' C3 C2 72.8(4) . . ? C1' C3 C2 112.9(4) . . ? C1' C3 C2 67.1(4) 2_667 . ? C2' C3 C2 72.8(4) 2_667 2_667 ? C2' C3 C2 107.2(4) . 2_667 ? C1' C3 C2 67.1(4) . 2_667 ? C1' C3 C2 112.9(4) 2_667 2_667 ? C2 C3 C2 180.000(2) . 2_667 ? C2' C3 C1 66.6(4) 2_667 . ? C2' C3 C1 113.4(4) . . ? C1' C3 C1 73.9(4) . . ? C1' C3 C1 106.1(4) 2_667 . ? C2 C3 C1 77.5(4) . . ? C2 C3 C1 102.5(4) 2_667 . ? C2' C3 C1 113.4(4) 2_667 2_667 ? C2' C3 C1 66.6(4) . 2_667 ? C1' C3 C1 106.1(4) . 2_667 ? C1' C3 C1 73.9(4) 2_667 2_667 ? C2 C3 C1 102.5(4) . 2_667 ? C2 C3 C1 77.5(4) 2_667 2_667 ? C1 C3 C1 180.0(3) . 2_667 ? P2 N1 P1 120.5(2) . . ? P2 N2 P3 119.8(2) . . ? P3 N3 P1 114.2(2) . . ? C1 O1 C1' 74.2(4) . . ? C1 O1 P1 118.4(4) . . ? C1' O1 P1 115.5(4) . . ? C2 O2 C2' 73.1(4) . . ? C2 O2 P3 118.0(4) . . ? C2' O2 P3 115.7(3) . . ? N1 P1 O1 109.57(19) . . ? N1 P1 N3 116.56(18) . . ? O1 P1 N3 110.04(17) . . ? N1 P1 Cl1 109.07(14) . . ? O1 P1 Cl1 101.01(13) . . ? N3 P1 Cl1 109.46(15) . . ? N1 P1 P3 90.63(13) . . ? O1 P1 P3 103.77(12) . . ? N3 P1 P3 32.81(13) . . ? Cl1 P1 P3 140.77(7) . . ? N1 P2 N2 117.85(18) . . ? N1 P2 Cl3 109.85(15) . . ? N2 P2 Cl3 109.50(14) . . ? N1 P2 Cl2 108.34(15) . . ? N2 P2 Cl2 108.05(15) . . ? Cl3 P2 Cl2 102.05(7) . . ? N3 P3 N2 116.87(17) . . ? N3 P3 O2 110.41(17) . . ? N2 P3 O2 109.92(18) . . ? N3 P3 Cl4 108.67(14) . . ? N2 P3 Cl4 108.24(14) . . ? O2 P3 Cl4 101.61(12) . . ? N3 P3 P1 33.00(12) . . ? N2 P3 P1 90.98(13) . . ? O2 P3 P1 104.21(11) . . ? Cl4 P3 P1 140.00(8) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.736 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.119 data_1a _database_code_depnum_ccdc_archive 'CCDC 279224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Cl8 N6 O4 P6' _chemical_formula_weight 685.59 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 11.659(2) _cell_length_b 14.096(3) _cell_length_c 14.038(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.89(3) _cell_angle_gamma 90.00 _cell_volume 2306.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23263 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 52.16 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 1.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25062 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.54 _reflns_number_total 6075 _reflns_number_gt 5068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+3.8405P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6075 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _refine_ls_shift/su_max 0.013 _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 H8 H 0.868(2) 0.528(2) 1.1255(19) 0.021(7) Uiso 1 1 d . . . H4 H 0.798(2) 0.4474(19) 0.8844(19) 0.015(6) Uiso 1 1 d . . . H6 H 0.608(2) 0.527(2) 0.923(2) 0.027(7) Uiso 1 1 d . . . H2 H 0.649(2) 0.4207(19) 1.1046(19) 0.018(6) Uiso 1 1 d . . . H1 H 0.664(2) 0.375(2) 1.0001(19) 0.019(6) Uiso 1 1 d . . . H5 H 0.677(2) 0.6178(19) 0.9404(18) 0.015(6) Uiso 1 1 d . . . H7 H 0.834(2) 0.620(2) 1.067(2) 0.023(7) Uiso 1 1 d . . . H3 H 0.870(2) 0.536(2) 0.9138(18) 0.017(6) Uiso 1 1 d . . . P1 P 0.89678(5) 0.14187(4) 0.95853(4) 0.02076(13) Uani 1 1 d . . . P3 P 0.89596(5) 0.32596(4) 1.02598(4) 0.01849(13) Uani 1 1 d . . . P4 P 0.61409(5) 0.64215(4) 1.13316(4) 0.02004(13) Uani 1 1 d . . . P2 P 1.04340(5) 0.19477(4) 1.10330(4) 0.02074(13) Uani 1 1 d . . . P5 P 0.47377(5) 0.71621(4) 1.26909(4) 0.02076(13) Uani 1 1 d . . . P6 P 0.61687(6) 0.83367(4) 1.17265(4) 0.02345(14) Uani 1 1 d . . . Cl3 Cl 1.00539(6) 0.15353(5) 1.23604(5) 0.03476(16) Uani 1 1 d . . . Cl7 Cl 0.54839(7) 0.93900(5) 1.09616(5) 0.03646(16) Uani 1 1 d . . . Cl4 Cl 1.21368(5) 0.18979(5) 1.10649(5) 0.03190(15) Uani 1 1 d . . . Cl8 Cl 0.76054(7) 0.89569(6) 1.22079(5) 0.04374(19) Uani 1 1 d . . . Cl6 Cl 0.47151(7) 0.68771(5) 1.40708(4) 0.03851(17) Uani 1 1 d . . . Cl2 Cl 0.93922(7) 0.10039(5) 0.82861(5) 0.03979(17) Uani 1 1 d . . . Cl1 Cl 0.76658(6) 0.05550(5) 0.98553(7) 0.04390(19) Uani 1 1 d . . . Cl5 Cl 0.30830(6) 0.73070(7) 1.23687(6) 0.0529(2) Uani 1 1 d . . . O1 O 0.79624(14) 0.35620(12) 1.09382(12) 0.0238(3) Uani 1 1 d . . . O4 O 0.72357(14) 0.58419(12) 1.16436(11) 0.0232(3) Uani 1 1 d . . . O3 O 0.56903(13) 0.58957(12) 1.04083(12) 0.0227(3) Uani 1 1 d . . . O2 O 0.92558(13) 0.41949(11) 0.97038(11) 0.0204(3) Uani 1 1 d . . . C1 C 0.70116(19) 0.41011(16) 1.05242(17) 0.0218(4) Uani 1 1 d . . . N5 N 0.52056(18) 0.62881(14) 1.21268(16) 0.0269(4) Uani 1 1 d . . . N4 N 0.64768(19) 0.74839(14) 1.10654(15) 0.0266(4) Uani 1 1 d . . . N2 N 0.85264(18) 0.24727(14) 0.95328(15) 0.0262(4) Uani 1 1 d . . . C4 C 0.64999(19) 0.56143(16) 0.96824(16) 0.0200(4) Uani 1 1 d . . . C3 C 0.74802(18) 0.50329(15) 1.01244(15) 0.0173(4) Uani 1 1 d . . . C2 C 0.83372(18) 0.48041(15) 0.93449(15) 0.0180(4) Uani 1 1 d . . . C5 C 0.80602(19) 0.56179(17) 1.09069(16) 0.0208(4) Uani 1 1 d . . . N3 N 1.00496(17) 0.30125(14) 1.09019(14) 0.0235(4) Uani 1 1 d . . . N1 N 0.99820(19) 0.11780(14) 1.03044(16) 0.0285(5) Uani 1 1 d . . . N6 N 0.5364(2) 0.81539(15) 1.26048(16) 0.0318(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0211(3) 0.0155(3) 0.0257(3) -0.0023(2) -0.0014(2) 0.0000(2) P3 0.0204(3) 0.0133(3) 0.0217(3) 0.0003(2) -0.0010(2) 0.0024(2) P4 0.0185(3) 0.0172(3) 0.0245(3) -0.0018(2) 0.0042(2) 0.0017(2) P2 0.0219(3) 0.0165(3) 0.0237(3) 0.0006(2) -0.0032(2) 0.0034(2) P5 0.0209(3) 0.0211(3) 0.0204(3) -0.0012(2) 0.0029(2) 0.0029(2) P6 0.0326(3) 0.0167(3) 0.0210(3) 0.0006(2) 0.0010(2) -0.0027(2) Cl3 0.0407(4) 0.0348(3) 0.0288(3) 0.0087(3) 0.0042(2) 0.0081(3) Cl7 0.0537(4) 0.0226(3) 0.0329(3) 0.0061(2) -0.0044(3) 0.0028(3) Cl4 0.0207(3) 0.0322(3) 0.0427(3) -0.0023(3) -0.0025(2) 0.0039(2) Cl8 0.0461(4) 0.0468(4) 0.0381(4) -0.0026(3) -0.0087(3) -0.0184(3) Cl6 0.0594(4) 0.0338(3) 0.0225(3) 0.0045(2) 0.0041(3) -0.0055(3) Cl2 0.0529(4) 0.0376(4) 0.0290(3) -0.0074(3) 0.0042(3) 0.0081(3) Cl1 0.0277(3) 0.0280(3) 0.0762(5) 0.0024(3) 0.0083(3) -0.0069(3) Cl5 0.0255(3) 0.0745(6) 0.0584(5) -0.0303(4) -0.0101(3) 0.0182(3) O1 0.0254(8) 0.0204(8) 0.0257(8) 0.0070(6) 0.0038(6) 0.0048(6) O4 0.0217(8) 0.0275(8) 0.0205(7) -0.0045(6) 0.0019(6) 0.0051(7) O3 0.0161(7) 0.0228(8) 0.0294(8) -0.0051(7) 0.0000(6) 0.0032(6) O2 0.0188(7) 0.0166(7) 0.0261(8) 0.0031(6) 0.0041(6) 0.0037(6) C1 0.0197(10) 0.0184(10) 0.0274(11) 0.0033(9) 0.0037(9) 0.0010(8) N5 0.0264(10) 0.0197(9) 0.0349(11) -0.0008(8) 0.0121(8) 0.0003(8) N4 0.0334(11) 0.0193(9) 0.0273(10) -0.0010(8) 0.0104(8) -0.0030(8) N2 0.0296(11) 0.0183(9) 0.0305(10) -0.0030(8) -0.0109(8) 0.0036(8) C4 0.0183(10) 0.0189(10) 0.0226(10) -0.0015(9) -0.0001(8) 0.0012(8) C3 0.0172(10) 0.0147(9) 0.0200(9) -0.0011(8) 0.0005(7) 0.0003(8) C2 0.0179(10) 0.0153(10) 0.0207(10) 0.0018(8) 0.0003(8) 0.0018(8) C5 0.0172(10) 0.0212(11) 0.0240(11) -0.0042(9) 0.0006(8) 0.0013(8) N3 0.0260(10) 0.0177(9) 0.0265(10) -0.0016(7) -0.0066(8) 0.0024(8) N1 0.0322(11) 0.0149(9) 0.0380(11) -0.0025(8) -0.0110(9) 0.0056(8) N6 0.0482(14) 0.0196(10) 0.0280(11) -0.0030(8) 0.0116(9) -0.0005(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N2 1.574(2) . ? P1 N1 1.580(2) . ? P1 Cl2 1.9852(10) . ? P1 Cl1 1.9870(9) . ? P3 O2 1.5731(16) . ? P3 O1 1.5731(18) . ? P3 N3 1.585(2) . ? P3 N2 1.585(2) . ? P4 O4 1.5720(17) . ? P4 O3 1.5761(17) . ? P4 N5 1.584(2) . ? P4 N4 1.594(2) . ? P2 N3 1.576(2) . ? P2 N1 1.576(2) . ? P2 Cl4 1.9863(9) . ? P2 Cl3 2.0081(9) . ? P5 N5 1.567(2) . ? P5 N6 1.583(2) . ? P5 Cl6 1.9790(9) . ? P5 Cl5 1.9852(10) . ? P6 N4 1.564(2) . ? P6 N6 1.582(2) . ? P6 Cl7 1.9921(9) . ? P6 Cl8 1.9980(10) . ? O1 C1 1.457(3) . ? O4 C5 1.457(3) . ? O3 C4 1.455(3) . ? O2 C2 1.457(3) . ? C1 C3 1.532(3) . ? C4 C3 1.530(3) . ? C3 C5 1.523(3) . ? C3 C2 1.528(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 P1 N1 118.27(11) . . ? N2 P1 Cl2 108.72(9) . . ? N1 P1 Cl2 109.22(9) . . ? N2 P1 Cl1 109.70(9) . . ? N1 P1 Cl1 108.24(9) . . ? Cl2 P1 Cl1 101.35(5) . . ? O2 P3 O1 104.08(9) . . ? O2 P3 N3 106.62(10) . . ? O1 P3 N3 107.98(10) . . ? O2 P3 N2 109.71(10) . . ? O1 P3 N2 110.39(11) . . ? N3 P3 N2 117.20(11) . . ? O4 P4 O3 104.11(9) . . ? O4 P4 N5 107.87(11) . . ? O3 P4 N5 107.42(11) . . ? O4 P4 N4 110.63(11) . . ? O3 P4 N4 109.21(11) . . ? N5 P4 N4 116.82(11) . . ? N3 P2 N1 119.21(11) . . ? N3 P2 Cl4 108.58(8) . . ? N1 P2 Cl4 108.32(9) . . ? N3 P2 Cl3 108.51(8) . . ? N1 P2 Cl3 109.05(9) . . ? Cl4 P2 Cl3 101.75(5) . . ? N5 P5 N6 119.41(11) . . ? N5 P5 Cl6 110.19(9) . . ? N6 P5 Cl6 105.50(9) . . ? N5 P5 Cl5 108.08(9) . . ? N6 P5 Cl5 109.87(10) . . ? Cl6 P5 Cl5 102.50(5) . . ? N4 P6 N6 118.80(11) . . ? N4 P6 Cl7 110.29(9) . . ? N6 P6 Cl7 107.71(9) . . ? N4 P6 Cl8 109.75(9) . . ? N6 P6 Cl8 108.16(10) . . ? Cl7 P6 Cl8 100.56(5) . . ? C1 O1 P3 117.68(14) . . ? C5 O4 P4 117.16(14) . . ? C4 O3 P4 119.51(14) . . ? C2 O2 P3 119.98(13) . . ? O1 C1 C3 108.64(17) . . ? P5 N5 P4 120.78(13) . . ? P6 N4 P4 121.57(13) . . ? P1 N2 P3 122.00(13) . . ? O3 C4 C3 110.52(18) . . ? C5 C3 C2 110.05(17) . . ? C5 C3 C4 108.84(18) . . ? C2 C3 C4 108.38(17) . . ? C5 C3 C1 110.90(18) . . ? C2 C3 C1 108.79(17) . . ? C4 C3 C1 109.84(18) . . ? O2 C2 C3 111.24(17) . . ? O4 C5 C3 109.79(17) . . ? P2 N3 P3 119.97(13) . . ? P2 N1 P1 120.42(13) . . ? P5 N6 P6 118.90(13) . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.861 _refine_diff_density_max 0.717 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.096 data_04src0981 _database_code_depnum_ccdc_archive 'CCDC 279225' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H48 Cl4 N10 O4 P6' _chemical_formula_weight 832.31 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 10.659(9) _cell_length_b 11.329(13) _cell_length_c 17.94(4) _cell_angle_alpha 83.85(11) _cell_angle_beta 74.77(12) _cell_angle_gamma 67.20(13) _cell_volume 1926(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6280 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9425 _exptl_absorpt_correction_T_max 0.9940 _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 26273 _diffrn_reflns_av_R_equivalents 0.1090 _diffrn_reflns_av_sigmaI/netI 0.1032 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7656 _reflns_number_gt 5169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (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^)+(0.1092P)^2^+21.5992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7656 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1808 _refine_ls_R_factor_gt 0.1325 _refine_ls_wR_factor_ref 0.3299 _refine_ls_wR_factor_gt 0.3043 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.003 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 0.4295(13) 1.3107(11) 0.0596(6) 0.045(3) Uani 1 1 d . . . C2 C 0.503(2) 1.3209(18) 0.1212(12) 0.095(6) Uani 1 1 d . . . H2A H 0.5980 1.2559 0.1113 0.142 Uiso 1 1 calc R . . H2B H 0.4495 1.3071 0.1727 0.142 Uiso 1 1 calc R . . H2C H 0.5067 1.4063 0.1186 0.142 Uiso 1 1 calc R . . C3 C 0.505(3) 1.3141(18) -0.0197(10) 0.129(10) Uani 1 1 d . . . H3A H 0.5421 1.2285 -0.0421 0.193 Uiso 1 1 calc R . . H3B H 0.5822 1.3415 -0.0218 0.193 Uiso 1 1 calc R . . H3C H 0.4409 1.3746 -0.0491 0.193 Uiso 1 1 calc R . . C4 C 0.2894(18) 1.4263(14) 0.0742(11) 0.084(5) Uani 1 1 d . . . H4A H 0.3074 1.5055 0.0616 0.125 Uiso 1 1 calc R . . H4B H 0.2399 1.4274 0.1287 0.125 Uiso 1 1 calc R . . H4C H 0.2316 1.4197 0.0416 0.125 Uiso 1 1 calc R . . C5 C 0.2282(14) 1.1518(13) -0.0864(6) 0.052(3) Uani 1 1 d . . . C6 C 0.1379(18) 1.0737(17) -0.0528(8) 0.075(5) Uani 1 1 d . . . H6A H 0.1983 0.9850 -0.0448 0.113 Uiso 1 1 calc R . . H6B H 0.0821 1.0753 -0.0888 0.113 Uiso 1 1 calc R . . H6C H 0.0751 1.1104 -0.0033 0.113 Uiso 1 1 calc R . . C7 C 0.1356(16) 1.2926(16) -0.0958(8) 0.073(4) Uani 1 1 d . . . H7A H 0.0807 1.3291 -0.0448 0.109 Uiso 1 1 calc R . . H7B H 0.0720 1.2980 -0.1279 0.109 Uiso 1 1 calc R . . H7C H 0.1950 1.3405 -0.1205 0.109 Uiso 1 1 calc R . . C8 C 0.3183(17) 1.1013(17) -0.1664(7) 0.075(5) Uani 1 1 d . . . H8A H 0.3594 1.1629 -0.1928 0.113 Uiso 1 1 calc R . . H8B H 0.2599 1.0893 -0.1967 0.113 Uiso 1 1 calc R . . H8C H 0.3934 1.0191 -0.1610 0.113 Uiso 1 1 calc R . . C9 C 0.2412(10) 0.8491(9) 0.2954(5) 0.029(2) Uani 1 1 d . . . H9A H 0.1591 0.9185 0.3253 0.034 Uiso 1 1 calc R . . H9B H 0.3057 0.8063 0.3295 0.034 Uiso 1 1 calc R . . C10 C 0.1931(10) 0.7536(9) 0.2711(5) 0.027(2) Uani 1 1 d . . . C11 C 0.0988(10) 0.8172(11) 0.2150(5) 0.035(2) Uani 1 1 d . . . H11A H 0.0696 0.7537 0.1979 0.042 Uiso 1 1 calc R . . H11B H 0.0134 0.8876 0.2414 0.042 Uiso 1 1 calc R . . C12 C 0.3159(10) 0.6383(9) 0.2300(5) 0.028(2) Uani 1 1 d . . . H12A H 0.2797 0.5836 0.2095 0.034 Uiso 1 1 calc R . . H12B H 0.3748 0.6682 0.1860 0.034 Uiso 1 1 calc R . . C13 C 0.1053(10) 0.7090(11) 0.3421(6) 0.034(2) Uani 1 1 d . . . H13A H 0.0266 0.7840 0.3689 0.041 Uiso 1 1 calc R . . H13B H 0.0657 0.6531 0.3256 0.041 Uiso 1 1 calc R . . C14 C 0.7379(10) 0.1396(9) 0.4294(5) 0.028(2) Uani 1 1 d . . . C15 C 0.8774(10) 0.1421(10) 0.4321(6) 0.034(2) Uani 1 1 d . . . H15A H 0.9446 0.0542 0.4345 0.052 Uiso 1 1 calc R . . H15B H 0.8654 0.1889 0.4780 0.052 Uiso 1 1 calc R . . H15C H 0.9126 0.1848 0.3856 0.052 Uiso 1 1 calc R . . C16 C 0.6836(11) 0.0727(10) 0.5022(6) 0.037(2) Uani 1 1 d . . . H16A H 0.5916 0.0735 0.5015 0.055 Uiso 1 1 calc R . . H16B H 0.6749 0.1178 0.5480 0.055 Uiso 1 1 calc R . . H16C H 0.7494 -0.0161 0.5035 0.055 Uiso 1 1 calc R . . C17 C 0.7534(12) 0.0717(11) 0.3573(6) 0.038(2) Uani 1 1 d . . . H17A H 0.6633 0.0678 0.3571 0.057 Uiso 1 1 calc R . . H17B H 0.8239 -0.0153 0.3565 0.057 Uiso 1 1 calc R . . H17C H 0.7833 0.1188 0.3115 0.057 Uiso 1 1 calc R . . C18 C 0.3088(9) 0.3549(9) 0.6112(5) 0.026(2) Uani 1 1 d . . . C19 C 0.3260(10) 0.3924(10) 0.6867(5) 0.033(2) Uani 1 1 d . . . H19A H 0.4039 0.3233 0.7029 0.049 Uiso 1 1 calc R . . H19B H 0.2394 0.4068 0.7271 0.049 Uiso 1 1 calc R . . H19C H 0.3457 0.4711 0.6784 0.049 Uiso 1 1 calc R . . C20 C 0.2904(10) 0.2279(9) 0.6231(5) 0.030(2) Uani 1 1 d . . . H20A H 0.2750 0.2051 0.5759 0.045 Uiso 1 1 calc R . . H20B H 0.2094 0.2346 0.6662 0.045 Uiso 1 1 calc R . . H20C H 0.3749 0.1615 0.6347 0.045 Uiso 1 1 calc R . . C21 C 0.1825(10) 0.4598(11) 0.5887(6) 0.037(2) Uani 1 1 d . . . H21A H 0.1959 0.5414 0.5830 0.055 Uiso 1 1 calc R . . H21B H 0.0974 0.4675 0.6290 0.055 Uiso 1 1 calc R . . H21C H 0.1730 0.4377 0.5396 0.055 Uiso 1 1 calc R . . N1 N 0.0849(10) 1.0906(9) 0.2093(5) 0.043(2) Uani 1 1 d . . . N2 N 0.1335(10) 1.2422(9) 0.0880(5) 0.042(2) Uani 1 1 d . . . N3 N 0.3256(9) 1.0039(8) 0.0943(5) 0.036(2) Uani 1 1 d . . . N4 N 0.4070(11) 1.1880(10) 0.0761(6) 0.054(3) Uani 1 1 d . . . H4 H 0.4654 1.1301 0.1005 0.065 Uiso 1 1 calc R . . N5 N 0.3227(11) 1.1430(10) -0.0374(5) 0.051(3) Uani 1 1 d . . . H5 H 0.4082 1.1360 -0.0624 0.061 Uiso 1 1 calc R . . N6 N 0.4229(8) 0.4727(7) 0.4171(4) 0.0260(17) Uani 1 1 d . . . N7 N 0.3932(8) 0.2470(7) 0.4411(4) 0.0237(16) Uani 1 1 d . . . N8 N 0.2681(8) 0.4147(8) 0.3395(4) 0.0307(19) Uani 1 1 d . . . N9 N 0.6401(8) 0.2749(7) 0.4268(4) 0.0243(16) Uani 1 1 d . . . H9 H 0.6791 0.3300 0.4056 0.029 Uiso 1 1 calc R . . N10 N 0.4422(8) 0.3408(7) 0.5527(4) 0.0255(17) Uani 1 1 d . . . H10 H 0.5138 0.3352 0.5704 0.031 Uiso 1 1 calc R . . O1 O 0.3118(7) 0.9037(7) 0.2293(3) 0.0317(15) Uani 1 1 d . . . O2 O 0.1761(7) 0.8678(7) 0.1481(3) 0.0316(15) Uani 1 1 d . . . O3 O 0.3999(6) 0.5645(6) 0.2830(3) 0.0252(14) Uani 1 1 d . . . O4 O 0.1923(6) 0.6396(6) 0.3940(3) 0.0289(15) Uani 1 1 d . . . P1 P 0.2234(3) 0.9749(3) 0.16786(13) 0.0305(6) Uani 1 1 d . . . P2 P 0.0426(3) 1.2236(3) 0.16862(15) 0.0408(7) Uani 1 1 d . . . P3 P 0.2920(3) 1.1441(3) 0.05625(14) 0.0350(7) Uani 1 1 d . . . P4 P 0.3245(3) 0.5138(2) 0.36072(13) 0.0257(6) Uani 1 1 d . . . P5 P 0.4692(2) 0.3345(2) 0.45837(13) 0.0234(5) Uani 1 1 d . . . P6 P 0.2957(3) 0.2837(3) 0.38436(14) 0.0282(6) Uani 1 1 d . . . Cl1 Cl 0.0188(4) 1.3533(3) 0.24492(17) 0.0624(10) Uani 1 1 d . . . Cl2 Cl -0.1558(4) 1.2785(4) 0.1605(2) 0.0729(11) Uani 1 1 d . . . Cl3 Cl 0.1084(3) 0.2768(3) 0.44194(15) 0.0387(6) Uani 1 1 d . . . Cl4 Cl 0.3606(3) 0.1420(3) 0.30818(16) 0.0448(7) 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 0.063(8) 0.038(7) 0.046(6) 0.006(5) -0.016(5) -0.031(6) C2 0.107(14) 0.076(13) 0.128(16) 0.016(11) -0.059(12) -0.047(11) C3 0.23(2) 0.075(13) 0.074(11) -0.022(9) 0.059(13) -0.105(16) C4 0.089(12) 0.038(10) 0.128(15) -0.004(9) -0.028(10) -0.026(9) C5 0.068(8) 0.066(9) 0.031(6) 0.008(5) -0.018(5) -0.032(7) C6 0.101(12) 0.113(14) 0.044(7) 0.011(8) -0.036(7) -0.066(11) C7 0.079(10) 0.087(12) 0.047(8) 0.011(7) -0.031(7) -0.018(9) C8 0.101(12) 0.100(13) 0.031(6) 0.011(7) -0.023(7) -0.042(10) C9 0.036(5) 0.026(6) 0.020(4) 0.005(3) -0.007(4) -0.010(4) C10 0.029(5) 0.027(6) 0.023(4) 0.009(4) -0.010(3) -0.008(4) C11 0.032(5) 0.043(7) 0.035(5) 0.017(4) -0.012(4) -0.022(5) C12 0.036(5) 0.019(5) 0.024(4) 0.002(3) -0.009(4) -0.004(4) C13 0.023(5) 0.038(7) 0.041(5) 0.017(4) -0.019(4) -0.008(5) C14 0.027(5) 0.012(5) 0.041(5) 0.009(4) -0.009(4) -0.006(4) C15 0.029(5) 0.017(6) 0.054(6) 0.001(4) -0.012(4) -0.004(4) C16 0.040(6) 0.026(6) 0.042(6) 0.006(4) -0.006(4) -0.013(5) C17 0.044(6) 0.036(7) 0.040(6) -0.001(4) -0.007(4) -0.022(5) C18 0.024(5) 0.026(6) 0.026(4) 0.003(4) -0.006(3) -0.009(4) C19 0.032(5) 0.040(7) 0.029(5) 0.004(4) -0.005(4) -0.019(5) C20 0.024(5) 0.028(6) 0.036(5) 0.001(4) -0.003(4) -0.011(4) C21 0.021(5) 0.048(7) 0.035(5) -0.006(4) -0.004(4) -0.006(5) N1 0.044(5) 0.035(6) 0.038(5) 0.006(4) -0.007(4) -0.005(4) N2 0.057(6) 0.032(6) 0.031(4) 0.009(4) -0.010(4) -0.012(5) N3 0.037(5) 0.031(5) 0.031(4) 0.002(3) -0.002(3) -0.007(4) N4 0.066(7) 0.044(7) 0.067(7) 0.025(5) -0.027(5) -0.037(6) N5 0.058(6) 0.060(7) 0.036(5) 0.016(4) -0.014(4) -0.026(6) N6 0.027(4) 0.018(5) 0.036(4) 0.000(3) -0.013(3) -0.008(3) N7 0.027(4) 0.022(4) 0.024(4) 0.005(3) -0.011(3) -0.008(3) N8 0.030(4) 0.035(5) 0.036(4) 0.015(3) -0.020(3) -0.020(4) N9 0.031(4) 0.016(4) 0.029(4) 0.005(3) -0.012(3) -0.011(3) N10 0.026(4) 0.026(5) 0.028(4) 0.003(3) -0.009(3) -0.013(4) O1 0.039(4) 0.035(4) 0.026(3) 0.010(3) -0.013(3) -0.019(3) O2 0.038(4) 0.036(4) 0.024(3) 0.010(3) -0.011(3) -0.017(3) O3 0.023(3) 0.024(4) 0.028(3) 0.004(2) -0.008(2) -0.008(3) O4 0.028(3) 0.028(4) 0.023(3) 0.006(3) -0.006(2) -0.004(3) P1 0.0384(15) 0.0280(15) 0.0222(12) 0.0049(9) -0.0071(10) -0.0108(12) P2 0.0459(17) 0.0378(18) 0.0309(14) 0.0023(11) -0.0097(11) -0.0079(14) P3 0.0490(17) 0.0309(17) 0.0289(13) 0.0081(10) -0.0125(11) -0.0189(13) P4 0.0270(12) 0.0234(14) 0.0272(12) 0.0022(9) -0.0075(9) -0.0098(11) P5 0.0236(12) 0.0229(14) 0.0245(11) 0.0031(9) -0.0079(8) -0.0090(10) P6 0.0280(13) 0.0263(15) 0.0355(13) 0.0007(10) -0.0125(10) -0.0129(11) Cl1 0.088(2) 0.0386(19) 0.0389(15) -0.0070(12) -0.0080(15) -0.0042(17) Cl2 0.0467(18) 0.085(3) 0.075(2) 0.0249(19) -0.0245(16) -0.0132(19) Cl3 0.0285(12) 0.0404(17) 0.0537(15) 0.0117(11) -0.0168(10) -0.0185(12) Cl4 0.0533(17) 0.0395(17) 0.0458(15) -0.0118(12) -0.0184(12) -0.0147(14) _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 C3 1.443(18) . ? C1 N4 1.487(14) . ? C1 C4 1.54(2) . ? C1 C2 1.545(19) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N5 1.472(15) . ? C5 C6 1.521(18) . ? C5 C8 1.529(18) . ? C5 C7 1.53(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O1 1.446(11) . ? C9 C10 1.507(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.529(13) . ? C10 C13 1.535(13) . ? C10 C11 1.536(12) . ? C11 O2 1.466(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O3 1.449(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.441(10) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N9 1.486(12) . ? C14 C15 1.511(13) . ? C14 C17 1.515(14) . ? C14 C16 1.531(13) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N10 1.491(11) . ? C18 C20 1.512(14) . ? C18 C21 1.527(14) . ? C18 C19 1.538(13) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 P2 1.555(10) . ? N1 P1 1.607(10) . ? N2 P2 1.559(9) . ? N2 P3 1.609(10) . ? N3 P1 1.570(9) . ? N3 P3 1.604(9) . ? N4 P3 1.617(10) . ? N4 H4 0.8800 . ? N5 P3 1.624(10) . ? N5 H5 0.8800 . ? N6 P4 1.556(8) . ? N6 P5 1.608(8) . ? N7 P6 1.556(7) . ? N7 P5 1.598(8) . ? N8 P6 1.570(8) . ? N8 P4 1.582(8) . ? N9 P5 1.638(8) . ? N9 H9 0.8800 . ? N10 P5 1.644(8) . ? N10 H10 0.8800 . ? O1 P1 1.588(7) . ? O2 P1 1.586(7) . ? O3 P4 1.587(7) . ? O4 P4 1.599(8) . ? P2 Cl2 2.001(5) . ? P2 Cl1 2.014(5) . ? P6 Cl4 2.009(5) . ? P6 Cl3 2.020(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 N4 110.1(11) . . ? C3 C1 C4 108.9(14) . . ? N4 C1 C4 111.3(11) . . ? C3 C1 C2 115.7(15) . . ? N4 C1 C2 105.7(11) . . ? C4 C1 C2 105.0(13) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N5 C5 C6 111.3(10) . . ? N5 C5 C8 107.9(11) . . ? C6 C5 C8 109.7(12) . . ? N5 C5 C7 109.7(11) . . ? C6 C5 C7 110.4(13) . . ? C8 C5 C7 107.7(11) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 C10 111.4(7) . . ? O1 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? O1 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C12 112.2(8) . . ? C9 C10 C13 109.6(8) . . ? C12 C10 C13 110.1(8) . . ? C9 C10 C11 109.9(8) . . ? C12 C10 C11 107.5(8) . . ? C13 C10 C11 107.4(7) . . ? O2 C11 C10 109.3(7) . . ? O2 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? O2 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O3 C12 C10 110.4(7) . . ? O3 C12 H12A 109.6 . . ? C10 C12 H12A 109.6 . . ? O3 C12 H12B 109.6 . . ? C10 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O4 C13 C10 109.6(7) . . ? O4 C13 H13A 109.8 . . ? C10 C13 H13A 109.8 . . ? O4 C13 H13B 109.8 . . ? C10 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? N9 C14 C15 107.1(7) . . ? N9 C14 C17 109.2(8) . . ? C15 C14 C17 110.2(8) . . ? N9 C14 C16 110.3(8) . . ? C15 C14 C16 109.2(8) . . ? C17 C14 C16 110.9(8) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N10 C18 C20 109.7(8) . . ? N10 C18 C21 111.9(7) . . ? C20 C18 C21 111.2(8) . . ? N10 C18 C19 105.7(7) . . ? C20 C18 C19 108.9(8) . . ? C21 C18 C19 109.2(8) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? P2 N1 P1 119.2(6) . . ? P2 N2 P3 121.7(6) . . ? P1 N3 P3 122.1(6) . . ? C1 N4 P3 130.2(9) . . ? C1 N4 H4 114.9 . . ? P3 N4 H4 114.9 . . ? C5 N5 P3 129.3(8) . . ? C5 N5 H5 115.3 . . ? P3 N5 H5 115.3 . . ? P4 N6 P5 124.0(5) . . ? P6 N7 P5 124.5(5) . . ? P6 N8 P4 119.1(5) . . ? C14 N9 P5 128.3(6) . . ? C14 N9 H9 115.8 . . ? P5 N9 H9 115.8 . . ? C18 N10 P5 126.7(6) . . ? C18 N10 H10 116.7 . . ? P5 N10 H10 116.7 . . ? C9 O1 P1 116.0(6) . . ? C11 O2 P1 114.6(6) . . ? C12 O3 P4 118.3(6) . . ? C13 O4 P4 116.7(6) . . ? N3 P1 O2 109.3(4) . . ? N3 P1 O1 108.0(4) . . ? O2 P1 O1 101.9(4) . . ? N3 P1 N1 119.1(5) . . ? O2 P1 N1 107.8(5) . . ? O1 P1 N1 109.3(4) . . ? N1 P2 N2 119.7(5) . . ? N1 P2 Cl2 108.8(4) . . ? N2 P2 Cl2 108.3(4) . . ? N1 P2 Cl1 107.1(4) . . ? N2 P2 Cl1 111.2(4) . . ? Cl2 P2 Cl1 100.0(3) . . ? N3 P3 N2 114.1(5) . . ? N3 P3 N4 102.6(5) . . ? N2 P3 N4 113.0(6) . . ? N3 P3 N5 113.2(5) . . ? N2 P3 N5 107.4(5) . . ? N4 P3 N5 106.5(5) . . ? N6 P4 N8 119.4(4) . . ? N6 P4 O3 108.5(4) . . ? N8 P4 O3 108.5(4) . . ? N6 P4 O4 108.5(4) . . ? N8 P4 O4 108.0(4) . . ? O3 P4 O4 102.6(4) . . ? N7 P5 N6 112.9(4) . . ? N7 P5 N9 114.0(4) . . ? N6 P5 N9 103.7(4) . . ? N7 P5 N10 107.5(4) . . ? N6 P5 N10 113.9(4) . . ? N9 P5 N10 104.6(4) . . ? N7 P6 N8 119.4(4) . . ? N7 P6 Cl4 109.9(3) . . ? N8 P6 Cl4 109.0(4) . . ? N7 P6 Cl3 108.7(3) . . ? N8 P6 Cl3 108.1(4) . . ? Cl4 P6 Cl3 100.1(2) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 1.076 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.159 data_2a _database_code_depnum_ccdc_archive 'CCDC 279226' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Cl8 N6 O4 P6' _chemical_formula_weight 685.59 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 6.1615(12) _cell_length_b 7.8226(16) _cell_length_c 24.125(5) _cell_angle_alpha 96.23(3) _cell_angle_beta 95.03(3) _cell_angle_gamma 99.08(3) _cell_volume 1134.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13153 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 1.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8018 _exptl_absorpt_correction_T_max 0.9445 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15933 _diffrn_reflns_av_R_equivalents 0.1051 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4892 _reflns_number_gt 3792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+0.4954P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4892 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.004 _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 C1 C 0.4596(5) 0.7000(4) 0.27694(13) 0.0176(6) Uani 1 1 d . . . H1A H 0.5901 0.6438 0.2850 0.021 Uiso 1 1 calc R . . H1B H 0.5124 0.8249 0.2744 0.021 Uiso 1 1 calc R . . C2 C 0.3311(4) 0.6133(4) 0.22134(12) 0.0151(6) Uani 1 1 d . . . C3 C 0.1210(4) 0.6925(4) 0.21025(13) 0.0172(6) Uani 1 1 d . . . H3A H 0.1632 0.8163 0.2046 0.021 Uiso 1 1 calc R . . H3B H 0.0343 0.6301 0.1754 0.021 Uiso 1 1 calc R . . C4 C 0.2620(5) 0.4170(4) 0.22343(13) 0.0179(6) Uani 1 1 d . . . H4A H 0.1540 0.3996 0.2512 0.021 Uiso 1 1 calc R . . H4B H 0.1880 0.3616 0.1863 0.021 Uiso 1 1 calc R . . C5 C 0.4813(5) 0.6581(4) 0.17520(13) 0.0183(6) Uani 1 1 d . . . H5A H 0.4841 0.7817 0.1693 0.022 Uiso 1 1 calc R . . H5B H 0.6341 0.6434 0.1875 0.022 Uiso 1 1 calc R . . N1 N -0.0507(4) 0.6909(3) 0.36123(11) 0.0183(6) Uani 1 1 d . . . N2 N 0.1538(4) 0.9711(3) 0.31788(11) 0.0190(6) Uani 1 1 d . . . N3 N 0.0595(5) 1.0041(3) 0.42595(11) 0.0260(6) Uani 1 1 d . . . N4 N 0.3641(4) 0.0784(3) 0.15614(10) 0.0167(5) Uani 1 1 d . . . N5 N 0.3744(4) 0.2502(3) 0.06383(10) 0.0194(6) Uani 1 1 d . . . N6 N 0.6853(4) 0.3515(3) 0.15332(11) 0.0169(5) Uani 1 1 d . . . O1 O 0.3178(3) 0.6835(2) 0.32180(8) 0.0173(5) Uani 1 1 d . . . O2 O -0.0162(3) 0.6815(3) 0.25656(8) 0.0184(5) Uani 1 1 d . . . O3 O 0.4498(3) 0.3312(3) 0.23847(8) 0.0178(5) Uani 1 1 d . . . O4 O 0.4041(3) 0.5473(2) 0.12274(8) 0.0174(4) Uani 1 1 d . . . P1 P -0.04099(13) 0.80341(10) 0.42024(3) 0.01803(19) Uani 1 1 d . . . P2 P 0.09938(12) 0.76390(10) 0.31649(3) 0.01603(18) Uani 1 1 d . . . P3 P 0.17057(13) 1.08753(10) 0.37634(3) 0.0201(2) Uani 1 1 d . . . P4 P 0.54910(12) 0.22588(10) 0.19032(3) 0.01589(18) Uani 1 1 d . . . P5 P 0.28809(12) 0.08224(10) 0.09201(3) 0.01600(18) Uani 1 1 d . . . P6 P 0.54134(12) 0.40224(10) 0.10161(3) 0.01626(18) Uani 1 1 d . . . Cl1 Cl -0.34224(13) 0.77355(12) 0.44449(4) 0.0318(2) Uani 1 1 d . . . Cl2 Cl 0.12357(12) 0.69542(10) 0.47840(3) 0.02510(19) Uani 1 1 d . . . Cl3 Cl 0.48851(14) 1.18361(12) 0.40210(4) 0.0386(2) Uani 1 1 d . . . Cl4 Cl 0.05157(13) 1.30484(10) 0.36599(4) 0.0275(2) Uani 1 1 d . . . Cl5 Cl 0.76236(12) 0.11733(10) 0.23516(3) 0.02313(19) Uani 1 1 d . . . Cl6 Cl -0.04223(12) 0.03528(11) 0.08123(4) 0.0276(2) Uani 1 1 d . . . Cl7 Cl 0.35855(12) -0.12822(9) 0.04747(3) 0.02268(19) Uani 1 1 d . . . Cl8 Cl 0.74958(13) 0.51868(10) 0.05339(3) 0.02481(19) 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 0.0156(15) 0.0182(16) 0.0190(17) 0.0001(13) 0.0050(12) 0.0022(11) C2 0.0176(15) 0.0150(16) 0.0133(16) 0.0005(12) 0.0038(12) 0.0041(11) C3 0.0174(15) 0.0206(17) 0.0136(16) 0.0008(13) 0.0047(12) 0.0025(12) C4 0.0179(15) 0.0158(16) 0.0199(17) -0.0006(13) 0.0048(12) 0.0031(11) C5 0.0243(16) 0.0146(16) 0.0153(17) -0.0005(13) 0.0035(12) 0.0019(12) N1 0.0201(13) 0.0167(14) 0.0178(15) 0.0011(11) 0.0045(10) 0.0012(10) N2 0.0269(14) 0.0143(14) 0.0162(15) 0.0020(11) 0.0048(11) 0.0038(10) N3 0.0451(17) 0.0169(15) 0.0158(15) 0.0008(12) 0.0073(12) 0.0032(12) N4 0.0229(13) 0.0113(13) 0.0158(14) 0.0034(11) 0.0032(10) 0.0011(10) N5 0.0284(14) 0.0156(14) 0.0134(14) 0.0035(11) 0.0003(11) 0.0009(10) N6 0.0177(13) 0.0144(13) 0.0185(15) 0.0018(11) 0.0030(10) 0.0020(10) O1 0.0192(11) 0.0166(11) 0.0172(12) 0.0028(9) 0.0041(8) 0.0045(8) O2 0.0190(11) 0.0225(12) 0.0134(12) -0.0016(9) 0.0028(8) 0.0042(8) O3 0.0247(11) 0.0142(11) 0.0139(12) 0.0011(9) 0.0016(9) 0.0019(8) O4 0.0226(11) 0.0141(11) 0.0156(12) -0.0003(9) 0.0024(8) 0.0044(8) P1 0.0227(4) 0.0169(4) 0.0148(4) 0.0006(3) 0.0039(3) 0.0044(3) P2 0.0186(4) 0.0146(4) 0.0145(4) -0.0006(3) 0.0023(3) 0.0033(3) P3 0.0281(4) 0.0144(4) 0.0177(5) 0.0005(3) 0.0016(3) 0.0045(3) P4 0.0199(4) 0.0122(4) 0.0150(4) 0.0013(3) 0.0007(3) 0.0021(3) P5 0.0197(4) 0.0125(4) 0.0153(4) -0.0003(3) 0.0012(3) 0.0029(3) P6 0.0220(4) 0.0127(4) 0.0144(4) 0.0014(3) 0.0041(3) 0.0031(3) Cl1 0.0233(4) 0.0486(6) 0.0244(5) -0.0002(4) 0.0082(3) 0.0089(4) Cl2 0.0305(4) 0.0262(4) 0.0204(4) 0.0057(3) 0.0024(3) 0.0083(3) Cl3 0.0292(5) 0.0421(6) 0.0389(6) -0.0035(4) -0.0061(4) 0.0000(4) Cl4 0.0429(5) 0.0161(4) 0.0258(5) 0.0021(3) 0.0063(4) 0.0106(3) Cl5 0.0247(4) 0.0195(4) 0.0246(5) 0.0068(3) -0.0042(3) 0.0030(3) Cl6 0.0198(4) 0.0351(5) 0.0277(5) 0.0032(4) 0.0002(3) 0.0056(3) Cl7 0.0338(4) 0.0149(4) 0.0193(4) -0.0021(3) 0.0033(3) 0.0066(3) Cl8 0.0311(4) 0.0215(4) 0.0228(4) 0.0047(3) 0.0115(3) 0.0014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.453(3) . ? C1 C2 1.527(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C4 1.535(4) . ? C2 C3 1.536(4) . ? C2 C5 1.543(4) . ? C3 O2 1.461(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.464(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O4 1.451(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N1 P2 1.578(2) . ? N1 P1 1.582(3) . ? N2 P3 1.580(3) . ? N2 P2 1.598(3) . ? N3 P1 1.581(3) . ? N3 P3 1.581(3) . ? N4 P5 1.582(3) . ? N4 P4 1.588(3) . ? N5 P5 1.584(2) . ? N5 P6 1.586(3) . ? N6 P4 1.590(2) . ? N6 P6 1.589(3) . ? O1 P2 1.574(2) . ? O2 P2 1.576(2) . ? O3 P4 1.575(2) . ? O4 P6 1.586(2) . ? P1 Cl1 1.9812(11) . ? P1 Cl2 1.9971(12) . ? P3 Cl4 1.9858(12) . ? P3 Cl3 2.0022(13) . ? P4 Cl5 1.9799(12) . ? P4 P6 2.6700(13) . ? P5 Cl7 1.9942(12) . ? P5 Cl6 1.9989(11) . ? P6 Cl8 1.9879(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 O1 C1 C2 109.7(2) . . ? O1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C1 C2 C4 110.1(2) . . ? C1 C2 C3 110.0(2) . . ? C4 C2 C3 108.2(2) . . ? C1 C2 C5 106.4(2) . . ? C4 C2 C5 114.3(2) . . ? C3 C2 C5 107.7(2) . . ? O2 C3 C2 111.9(2) . . ? O2 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? O2 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O3 C4 C2 112.6(2) . . ? O3 C4 H4A 109.1 . . ? C2 C4 H4A 109.1 . . ? O3 C4 H4B 109.1 . . ? C2 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O4 C5 C2 111.4(2) . . ? O4 C5 H5A 109.3 . . ? C2 C5 H5A 109.3 . . ? O4 C5 H5B 109.3 . . ? C2 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? P2 N1 P1 118.94(16) . . ? P3 N2 P2 118.13(15) . . ? P1 N3 P3 121.38(18) . . ? P5 N4 P4 121.59(15) . . ? P5 N5 P6 117.32(16) . . ? P4 N6 P6 114.27(14) . . ? C1 O1 P2 117.53(17) . . ? C3 O2 P2 116.46(17) . . ? C4 O3 P4 118.52(18) . . ? C5 O4 P6 119.28(17) . . ? N3 P1 N1 118.18(14) . . ? N3 P1 Cl1 109.75(11) . . ? N1 P1 Cl1 108.31(10) . . ? N3 P1 Cl2 108.25(12) . . ? N1 P1 Cl2 109.30(10) . . ? Cl1 P1 Cl2 101.79(5) . . ? O1 P2 O2 103.59(11) . . ? O1 P2 N1 107.65(12) . . ? O2 P2 N1 107.69(13) . . ? O1 P2 N2 111.04(12) . . ? O2 P2 N2 108.86(13) . . ? N1 P2 N2 117.12(14) . . ? N2 P3 N3 118.39(14) . . ? N2 P3 Cl4 109.67(10) . . ? N3 P3 Cl4 108.09(11) . . ? N2 P3 Cl3 109.30(11) . . ? N3 P3 Cl3 108.92(12) . . ? Cl4 P3 Cl3 101.08(6) . . ? O3 P4 N4 110.67(12) . . ? O3 P4 N6 111.86(12) . . ? N4 P4 N6 115.23(13) . . ? O3 P4 Cl5 100.45(9) . . ? N4 P4 Cl5 109.73(9) . . ? N6 P4 Cl5 107.82(9) . . ? O3 P4 P6 107.62(8) . . ? N4 P4 P6 88.57(9) . . ? N6 P4 P6 32.86(9) . . ? Cl5 P4 P6 138.35(5) . . ? N5 P5 N4 118.71(13) . . ? N5 P5 Cl7 109.36(11) . . ? N4 P5 Cl7 109.03(10) . . ? N5 P5 Cl6 109.06(10) . . ? N4 P5 Cl6 108.04(10) . . ? Cl7 P5 Cl6 101.20(6) . . ? O4 P6 N5 107.62(13) . . ? O4 P6 N6 109.84(12) . . ? N5 P6 N6 117.66(13) . . ? O4 P6 Cl8 104.77(8) . . ? N5 P6 Cl8 108.80(10) . . ? N6 P6 Cl8 107.41(9) . . ? O4 P6 P4 100.04(8) . . ? N5 P6 P4 93.22(9) . . ? N6 P6 P4 32.87(9) . . ? Cl8 P6 P4 139.46(5) . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.467 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.112 data_2b _database_code_depnum_ccdc_archive 'CCDC 279227' _audit_creation_method 'manually at CCDC' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_sum C29H28Cl4N6O4P6 _chemical_formula_moiety ? _chemical_formula_weight 852.19 _chemical_melting_point ? 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 _symmetry_Int_Tables_number 14 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 14.170(3) _cell_length_b 7.6868(15) _cell_length_c 34.575(7) _cell_angle_alpha 90 _cell_angle_beta 94.89(3) _cell_angle_gamma 90 _cell_volume 3752.2 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.509 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_special_details ; ? ; _exptl_absorpt_correction_type multi-scan _exptl_absorpt_coefficient_mu 0.615 _exptl_crystal_F_000 1736 _diffrn_ambient_temperature 120 _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo k alpha' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_number 11151 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_av_R_equivalents ? _reflns_number_total 11151 _reflns_observed_criterion F2>2sigma(F2) _reflns_number_gt 6085 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1019 _refine_ls_number_reflns 6085 _refine_ls_hydrogen_treatment ? _refine_ls_number_parameters 443 _refine_ls_number_restraints ? _refine_special_details ; ; _refine_diff_density_max 0.394 _refine_diff_density_min -0.405 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C1 C 1.1571(3) 0.6843(6) -0.2507(1) C2 C 1.1764(4) 0.5648(7) -0.2788(1) C3 C 1.1275(5) 0.5743(10) -0.3152(2) C4 C 1.0631(5) 0.7038(10) -0.3240(2) C5 C 1.0436(5) 0.8199(9) -0.2960(2) C6 C 1.0895(4) 0.8126(7) -0.2593(1) C7 C 1.3270(3) 0.8092(5) -0.2083(1) C8 C 1.3204(3) 0.9785(6) -0.2223(1) C9 C 1.4010(5) 1.0782(7) -0.2241(2) C10 C 1.4877(4) 1.0095(9) -0.2129(2) C11 C 1.4948(4) 0.8423(9) -0.1986(2) C12 C 1.4149(3) 0.7401(6) -0.1971(1) C13 C 0.9856(3) 0.6475(5) -0.0982(1) C14 C 1.0198(2) 0.7775(5) -0.0667(1) C15 C 1.1279(2) 0.7917(5) -0.0643(1) C16 C 0.9822(2) 0.9625(5) -0.0768(1) C17 C 0.9974(2) 0.7100(5) -0.0268(1) C18 C 0.6606(3) 0.6327(5) -0.1087(1) C19 C 0.7169(3) 0.6674(6) -0.1383(1) C20 C 0.7221(4) 0.5497(7) -0.1685(2) C21 C 0.6686(3) 0.4013(7) -0.1699(2) C22 C 0.6122(3) 0.3663(6) -0.1405(1) C23 C 0.6078(3) 0.4814(5) -0.1098(1) C24 C 0.5464(3) 0.8015(5) -0.0536(1) C25 C 0.4797(3) 0.8875(5) -0.0785(1) C26 C 0.3903(3) 0.9208(6) -0.0667(2) C27 C 0.3680(3) 0.8668(6) -0.0308(2) C28 C 0.4317(3) 0.7784(6) -0.0064(2) C29 C 0.5219(3) 0.7457(5) -0.0180(1) N1 N 1.2529(2) 0.4867(4) -0.1921(1) N2 N 1.1717(2) 0.5121(4) -0.1239(1) N3 N 1.1568(2) 0.7816(4) -0.1748(1) N4 N 0.7064(2) 0.9601(4) -0.0792(1) N5 N 0.7238(2) 0.6763(4) -0.0310(1) N6 N 0.8405(2) 0.9543(3) -0.0181(1) O1 O 1.0195(2) 0.6933(3) -0.1350(1) O2 O 1.1612(2) 0.8326(3) -0.1015(1) O3 O 0.8826(2) 0.9662(3) -0.0899(1) O4 O 0.9028(2) 0.6395(3) -0.0268(1) P1 P 1.2218(1) 0.6835(1) -0.2037(1) P2 P 1.2383(1) 0.4139(1) -0.1506(1) P3 P 1.1311(1) 0.7000(1) -0.1357(1) P4 P 0.8058(1) 1.0202(1) -0.0610(1) P5 P 0.6645(1) 0.7740(1) -0.0669(1) P6 P 0.8185(1) 0.7528(1) -0.0125(1) Cl1 Cl 1.3650(1) 0.3827(2) -0.1202(1) Cl2 Cl 1.1976(1) 0.1670(1) -0.1547(1) Cl3 Cl 0.8117(1) 1.2797(1) -0.0593(1) Cl4 Cl 0.8279(1) 0.7091(1) 0.0450(1) H1 H 0.497441 0.928306 -0.106972 H2 H 0.338282 0.989249 -0.0857911 H3 H 0.298398 0.894931 -0.0216446 H4 H 0.412518 0.734154 0.0216184 H5 H 0.573092 0.675782 0.00118239 H6 H 0.563052 0.452704 -0.0867347 H7 H 0.570756 0.247782 -0.141268 H8 H 0.670752 0.312065 -0.194049 H9 H 0.768745 0.575481 -0.191067 H10 H 0.757319 0.787035 -0.138032 H11 H 1.07308 0.905866 -0.237373 H12 H 0.99094 0.919944 -0.302742 H13 H 1.02791 0.713995 -0.352969 H14 H 1.14048 0.477865 -0.336959 H15 H 1.22922 0.464667 -0.272451 H16 H 1.25176 1.03257 -0.231846 H17 H 1.39529 1.21112 -0.234423 H18 H 1.55102 1.08634 -0.215241 H19 H 1.56356 0.790467 -0.188446 H20 H 1.42131 0.606631 -0.187192 H21 H 1.02177 1.01504 -0.0995759 H22 H 0.993443 1.04312 -0.0511325 H23 H 1.00458 0.816571 -0.00627157 H24 H 1.04775 0.608758 -0.0178429 H25 H 1.15832 0.66881 -0.0542695 H26 H 1.15039 0.893338 -0.0438622 H27 H 0.908896 0.646501 -0.10113 H28 H 1.01152 0.519182 -0.0898608 data_3d _database_code_depnum_ccdc_archive 'CCDC 279228' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 Cl4 F8 N6 O8 P6' _chemical_formula_weight 863.94 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' F F 0.0171 0.0103 '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 Monocliniic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5294(4) _cell_length_b 21.3903(8) _cell_length_c 13.5881(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.728(2) _cell_angle_gamma 90.00 _cell_volume 2959.85(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8866 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 29.44 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.939 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9368 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' # absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.814 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.67510 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 30097 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7897 _reflns_number_gt 6524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0501P)^2^+1.3002P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7897 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _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 0.3567(2) -0.05884(10) 0.65191(16) 0.0216(4) Uani 1 1 d . . . H1A H 0.3449 -0.1047 0.6451 0.026 Uiso 1 1 calc R . . H1B H 0.4129 -0.0453 0.6075 0.026 Uiso 1 1 calc R . . C2 C 0.2244(2) -0.02653(10) 0.62006(16) 0.0212(4) Uani 1 1 d . . . C3 C 0.2277(2) 0.04464(10) 0.61438(16) 0.0220(4) Uani 1 1 d . . . C4 C 0.3004(2) 0.07809(10) 0.71031(17) 0.0234(4) Uani 1 1 d . . . H4A H 0.2769 0.1230 0.7055 0.028 Uiso 1 1 calc R . . H4B H 0.2750 0.0603 0.7698 0.028 Uiso 1 1 calc R . . C5 C 0.70857(19) -0.09867(9) 0.99434(15) 0.0183(4) Uani 1 1 d . . . H5A H 0.6424 -0.0951 0.9282 0.022 Uiso 1 1 calc R . . H5B H 0.6701 -0.1246 1.0398 0.022 Uiso 1 1 calc R . . C6 C 0.83099(19) -0.13195(9) 0.97763(15) 0.0171(4) Uani 1 1 d . . . C7 C 0.90194(19) -0.09723(9) 0.90809(15) 0.0187(4) Uani 1 1 d . . . H7A H 0.9500 -0.0610 0.9450 0.022 Uiso 1 1 calc R . . H7B H 0.9668 -0.1255 0.8899 0.022 Uiso 1 1 calc R . . C8 C 0.93698(19) -0.13693(10) 1.07870(15) 0.0195(4) Uani 1 1 d . . . H8A H 1.0170 -0.1553 1.0650 0.023 Uiso 1 1 calc R . . H8B H 0.9594 -0.0943 1.1058 0.023 Uiso 1 1 calc R . . C9 C 0.77851(19) -0.19472(9) 0.92840(15) 0.0193(4) Uani 1 1 d . . . H9A H 0.7301 -0.2165 0.9719 0.023 Uiso 1 1 calc R . . H9B H 0.7167 -0.1870 0.8613 0.023 Uiso 1 1 calc R . . C10 C 1.3872(2) -0.19634(10) 1.15148(17) 0.0235(4) Uani 1 1 d . . . H10A H 1.3809 -0.2043 1.2219 0.028 Uiso 1 1 calc R . . H10B H 1.4005 -0.1510 1.1439 0.028 Uiso 1 1 calc R . . C11 C 1.5011(2) -0.23230(10) 1.13111(16) 0.0223(4) Uani 1 1 d . . . C12 C 1.5099(2) -0.30205(10) 1.15983(17) 0.0229(4) Uani 1 1 d . . . C13 C 1.3859(2) -0.33980(10) 1.12004(18) 0.0237(4) Uani 1 1 d . . . H13A H 1.3549 -0.3348 1.0453 0.028 Uiso 1 1 calc R . . H13B H 1.4041 -0.3847 1.1352 0.028 Uiso 1 1 calc R . . N1 N 0.81137(16) 0.03238(8) 0.90439(12) 0.0170(3) Uani 1 1 d . . . N2 N 0.63561(17) 0.00349(9) 0.72699(13) 0.0204(3) Uani 1 1 d . . . N3 N 0.55554(17) 0.02149(9) 0.89992(13) 0.0205(3) Uani 1 1 d . . . N4 N 0.87970(17) -0.28814(8) 1.08520(13) 0.0209(3) Uani 1 1 d . . . N5 N 1.09243(17) -0.29445(9) 1.00726(14) 0.0234(4) Uani 1 1 d . . . N6 N 1.11195(17) -0.24439(9) 1.19516(14) 0.0233(4) Uani 1 1 d . . . O1 O 0.41838(14) -0.04293(7) 0.75608(11) 0.0199(3) Uani 1 1 d . . . O2 O 0.43900(14) 0.07116(7) 0.72320(11) 0.0218(3) Uani 1 1 d . . . O3 O 0.73589(14) -0.03649(6) 1.03847(10) 0.0177(3) Uani 1 1 d . . . O4 O 0.80959(14) -0.07562(7) 0.81590(11) 0.0199(3) Uani 1 1 d . . . O5 O 0.89972(14) -0.17423(7) 1.15637(11) 0.0204(3) Uani 1 1 d . . . O6 O 0.88607(15) -0.23406(7) 0.91546(11) 0.0208(3) Uani 1 1 d . . . O7 O 1.26883(15) -0.21610(7) 1.08032(12) 0.0237(3) Uani 1 1 d . . . O8 O 1.28617(14) -0.31856(7) 1.16753(12) 0.0242(3) Uani 1 1 d . . . F1 F 0.15186(12) -0.04174(6) 0.68616(10) 0.0280(3) Uani 1 1 d . . . F2 F 0.16022(13) -0.04917(7) 0.52746(10) 0.0321(3) Uani 1 1 d . . . F3 F 0.27982(14) 0.06012(7) 0.53602(10) 0.0310(3) Uani 1 1 d . . . F4 F 0.10157(13) 0.06572(7) 0.59008(11) 0.0338(3) Uani 1 1 d . . . F5 F 1.49811(14) -0.22829(7) 1.03125(10) 0.0310(3) Uani 1 1 d . . . F6 F 1.61460(13) -0.20448(7) 1.18272(11) 0.0323(3) Uani 1 1 d . . . F7 F 1.54711(13) -0.30539(7) 1.26273(10) 0.0316(3) Uani 1 1 d . . . F8 F 1.60648(13) -0.32778(7) 1.12461(12) 0.0346(3) Uani 1 1 d . . . P1 P 0.70248(5) 0.02275(2) 0.96608(4) 0.01630(10) Uani 1 1 d . . . P2 P 0.77889(5) -0.00340(2) 0.79813(4) 0.01614(10) Uani 1 1 d . . . P3 P 0.51936(5) 0.01327(2) 0.77983(4) 0.01728(11) Uani 1 1 d . . . P4 P 0.95689(5) -0.24347(3) 1.17359(4) 0.01900(11) Uani 1 1 d . . . P5 P 0.93778(5) -0.29136(2) 0.98832(4) 0.01842(11) Uani 1 1 d . . . P6 P 1.18094(5) -0.26893(3) 1.11119(4) 0.02002(11) Uani 1 1 d . . . Cl1 Cl 0.72656(5) 0.08964(2) 1.06983(4) 0.02348(11) Uani 1 1 d . . . Cl2 Cl 0.90438(5) 0.02602(3) 0.72101(4) 0.02312(11) Uani 1 1 d . . . Cl3 Cl 0.90587(6) -0.26536(3) 1.30000(4) 0.02922(12) Uani 1 1 d . . . Cl4 Cl 0.86127(6) -0.36581(2) 0.90804(4) 0.02777(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0193(10) 0.0222(10) 0.0223(10) -0.0032(8) 0.0036(8) -0.0008(7) C2 0.0170(9) 0.0235(10) 0.0209(10) -0.0012(8) 0.0007(8) -0.0027(8) C3 0.0166(9) 0.0232(10) 0.0232(10) 0.0035(8) -0.0005(8) 0.0014(8) C4 0.0160(9) 0.0220(10) 0.0297(11) -0.0016(8) 0.0010(8) 0.0037(8) C5 0.0158(9) 0.0173(9) 0.0214(9) 0.0003(7) 0.0038(7) -0.0011(7) C6 0.0155(9) 0.0168(9) 0.0173(9) 0.0012(7) 0.0012(7) 0.0004(7) C7 0.0159(9) 0.0198(9) 0.0197(9) 0.0030(7) 0.0033(7) 0.0023(7) C8 0.0172(9) 0.0203(10) 0.0189(9) 0.0014(7) 0.0010(7) -0.0009(7) C9 0.0168(9) 0.0188(9) 0.0202(9) -0.0008(7) 0.0009(7) -0.0001(7) C10 0.0225(10) 0.0188(10) 0.0273(11) -0.0006(8) 0.0028(8) -0.0004(8) C11 0.0190(10) 0.0234(10) 0.0238(10) -0.0010(8) 0.0040(8) -0.0042(8) C12 0.0185(9) 0.0243(10) 0.0255(10) 0.0005(8) 0.0051(8) 0.0022(8) C13 0.0198(10) 0.0189(10) 0.0324(11) -0.0002(8) 0.0063(9) 0.0007(8) N1 0.0151(8) 0.0196(8) 0.0163(8) -0.0013(6) 0.0040(6) -0.0008(6) N2 0.0164(8) 0.0288(9) 0.0146(8) 0.0004(7) 0.0014(6) 0.0009(7) N3 0.0143(8) 0.0288(9) 0.0183(8) 0.0012(7) 0.0041(6) 0.0024(7) N4 0.0200(8) 0.0218(8) 0.0207(8) 0.0028(7) 0.0050(7) -0.0012(7) N5 0.0189(8) 0.0280(10) 0.0234(9) -0.0012(7) 0.0053(7) 0.0023(7) N6 0.0186(8) 0.0304(10) 0.0185(8) 0.0014(7) 0.0003(7) 0.0020(7) O1 0.0163(7) 0.0203(7) 0.0212(7) 0.0026(6) 0.0016(5) -0.0014(5) O2 0.0153(7) 0.0198(7) 0.0269(8) 0.0049(6) -0.0008(6) 0.0001(5) O3 0.0182(7) 0.0185(7) 0.0160(6) 0.0004(5) 0.0036(5) -0.0001(5) O4 0.0235(7) 0.0184(7) 0.0164(7) 0.0005(5) 0.0023(6) 0.0009(6) O5 0.0204(7) 0.0224(7) 0.0183(7) 0.0010(6) 0.0046(6) -0.0001(6) O6 0.0234(7) 0.0194(7) 0.0200(7) 0.0019(6) 0.0061(6) 0.0024(6) O7 0.0199(7) 0.0239(8) 0.0253(8) 0.0066(6) 0.0023(6) -0.0003(6) O8 0.0187(7) 0.0229(7) 0.0308(8) 0.0093(6) 0.0062(6) 0.0028(6) F1 0.0201(6) 0.0316(7) 0.0333(7) 0.0016(6) 0.0087(5) -0.0032(5) F2 0.0287(7) 0.0350(8) 0.0261(7) -0.0064(6) -0.0049(6) -0.0058(6) F3 0.0338(7) 0.0334(7) 0.0236(7) 0.0068(5) 0.0034(6) -0.0040(6) F4 0.0161(6) 0.0333(7) 0.0449(8) 0.0038(6) -0.0053(6) 0.0045(5) F5 0.0341(7) 0.0360(8) 0.0264(7) 0.0040(6) 0.0140(6) -0.0016(6) F6 0.0209(6) 0.0295(7) 0.0434(8) -0.0040(6) 0.0023(6) -0.0070(5) F7 0.0263(7) 0.0370(8) 0.0281(7) 0.0088(6) 0.0009(6) 0.0017(6) F8 0.0239(7) 0.0301(7) 0.0542(9) -0.0023(7) 0.0180(6) 0.0045(5) P1 0.0144(2) 0.0184(2) 0.0158(2) 0.00006(18) 0.00339(18) 0.00089(17) P2 0.0141(2) 0.0190(2) 0.0152(2) 0.00093(18) 0.00358(18) -0.00054(18) P3 0.0134(2) 0.0193(2) 0.0177(2) 0.00212(19) 0.00143(18) 0.00038(18) P4 0.0174(2) 0.0227(3) 0.0160(2) 0.00244(19) 0.00270(19) 0.00078(19) P5 0.0184(2) 0.0177(2) 0.0184(2) 0.00070(19) 0.00330(19) -0.00027(18) P6 0.0166(2) 0.0210(3) 0.0215(3) 0.0042(2) 0.00327(19) 0.00174(19) Cl1 0.0283(3) 0.0224(2) 0.0205(2) -0.00415(18) 0.00756(19) 0.00006(19) Cl2 0.0207(2) 0.0292(3) 0.0216(2) 0.00129(19) 0.00947(18) -0.00322(19) Cl3 0.0295(3) 0.0397(3) 0.0193(2) 0.0067(2) 0.0077(2) 0.0017(2) Cl4 0.0362(3) 0.0203(2) 0.0262(3) -0.0040(2) 0.0070(2) -0.0060(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.440(2) . ? C1 C2 1.516(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 F2 1.357(2) . ? C2 F1 1.358(2) . ? C2 C3 1.525(3) . ? C3 F3 1.357(3) . ? C3 F4 1.361(2) . ? C3 C4 1.513(3) . ? C4 O2 1.433(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O3 1.457(2) . ? C5 C6 1.539(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.537(3) . ? C6 C7 1.537(3) . ? C6 C9 1.539(3) . ? C7 O4 1.452(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O5 1.454(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O6 1.457(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O7 1.433(3) . ? C10 C11 1.508(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 F5 1.352(2) . ? C11 F6 1.360(2) . ? C11 C12 1.539(3) . ? C12 F8 1.347(2) . ? C12 F7 1.355(3) . ? C12 C13 1.513(3) . ? C13 O8 1.438(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N1 P2 1.5927(17) . ? N1 P1 1.5963(17) . ? N2 P2 1.5782(17) . ? N2 P3 1.5827(18) . ? N3 P1 1.5797(18) . ? N3 P3 1.5882(18) . ? N4 P4 1.5874(19) . ? N4 P5 1.5878(19) . ? N5 P6 1.5784(19) . ? N5 P5 1.5840(18) . ? N6 P4 1.5839(19) . ? N6 P6 1.5897(19) . ? O1 P3 1.5829(15) . ? O2 P3 1.5843(15) . ? O3 P1 1.5879(14) . ? O4 P2 1.5840(15) . ? O5 P4 1.5934(15) . ? O6 P5 1.5827(15) . ? O7 P6 1.5833(16) . ? O8 P6 1.5840(15) . ? P1 Cl1 1.9793(7) . ? P1 P2 2.6649(7) . ? P2 Cl2 1.9860(7) . ? P4 Cl3 1.9819(7) . ? P4 P5 2.6777(8) . ? P5 Cl4 1.9820(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 108.96(17) . . ? 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 . . ? F2 C2 F1 107.25(16) . . ? F2 C2 C1 107.85(17) . . ? F1 C2 C1 109.41(17) . . ? F2 C2 C3 108.76(17) . . ? F1 C2 C3 107.25(17) . . ? C1 C2 C3 116.00(17) . . ? F3 C3 F4 107.04(17) . . ? F3 C3 C4 110.08(17) . . ? F4 C3 C4 107.52(18) . . ? F3 C3 C2 107.59(17) . . ? F4 C3 C2 108.04(17) . . ? C4 C3 C2 116.19(18) . . ? O2 C4 C3 109.45(17) . . ? O2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? O3 C5 C6 113.44(15) . . ? O3 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? O3 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C8 C6 C7 103.11(15) . . ? C8 C6 C5 110.20(16) . . ? C7 C6 C5 115.06(16) . . ? C8 C6 C9 115.26(16) . . ? C7 C6 C9 109.35(16) . . ? C5 C6 C9 104.24(15) . . ? O4 C7 C6 111.14(15) . . ? O4 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? O4 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O5 C8 C6 114.70(16) . . ? O5 C8 H8A 108.6 . . ? C6 C8 H8A 108.6 . . ? O5 C8 H8B 108.6 . . ? C6 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? O6 C9 C6 110.62(16) . . ? O6 C9 H9A 109.5 . . ? C6 C9 H9A 109.5 . . ? O6 C9 H9B 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? O7 C10 C11 108.74(17) . . ? O7 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? O7 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? F5 C11 F6 106.43(17) . . ? F5 C11 C10 109.59(18) . . ? F6 C11 C10 108.54(17) . . ? F5 C11 C12 107.49(17) . . ? F6 C11 C12 107.76(17) . . ? C10 C11 C12 116.57(18) . . ? F8 C12 F7 107.37(17) . . ? F8 C12 C13 108.42(18) . . ? F7 C12 C13 109.73(18) . . ? F8 C12 C11 107.95(17) . . ? F7 C12 C11 107.21(17) . . ? C13 C12 C11 115.84(18) . . ? O8 C13 C12 109.44(17) . . ? O8 C13 H13A 109.8 . . ? C12 C13 H13A 109.8 . . ? O8 C13 H13B 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? P2 N1 P1 113.36(10) . . ? P2 N2 P3 117.62(11) . . ? P1 N3 P3 122.07(11) . . ? P4 N4 P5 114.98(11) . . ? P6 N5 P5 118.67(12) . . ? P4 N6 P6 120.59(12) . . ? C1 O1 P3 119.44(13) . . ? C4 O2 P3 122.82(14) . . ? C5 O3 P1 118.94(12) . . ? C7 O4 P2 120.52(12) . . ? C8 O5 P4 117.06(13) . . ? C9 O6 P5 121.74(13) . . ? C10 O7 P6 119.89(13) . . ? C13 O8 P6 119.69(14) . . ? N3 P1 O3 111.69(9) . . ? N3 P1 N1 115.71(9) . . ? O3 P1 N1 110.66(8) . . ? N3 P1 Cl1 110.32(7) . . ? O3 P1 Cl1 99.64(6) . . ? N1 P1 Cl1 107.56(7) . . ? N3 P1 P2 88.53(7) . . ? O3 P1 P2 107.19(6) . . ? N1 P1 P2 33.28(6) . . ? Cl1 P1 P2 138.58(3) . . ? N2 P2 O4 108.10(9) . . ? N2 P2 N1 117.51(9) . . ? O4 P2 N1 110.00(8) . . ? N2 P2 Cl2 107.93(7) . . ? O4 P2 Cl2 104.61(6) . . ? N1 P2 Cl2 107.92(7) . . ? N2 P2 P1 93.17(7) . . ? O4 P2 P1 99.70(6) . . ? N1 P2 P1 33.36(6) . . ? Cl2 P2 P1 140.49(3) . . ? N2 P3 O1 111.34(9) . . ? N2 P3 O2 105.20(9) . . ? O1 P3 O2 104.27(8) . . ? N2 P3 N3 118.01(9) . . ? O1 P3 N3 105.47(9) . . ? O2 P3 N3 111.81(9) . . ? N6 P4 N4 115.98(10) . . ? N6 P4 O5 111.83(9) . . ? N4 P4 O5 110.29(9) . . ? N6 P4 Cl3 109.30(7) . . ? N4 P4 Cl3 108.30(7) . . ? O5 P4 Cl3 99.87(6) . . ? N6 P4 P5 89.82(7) . . ? N4 P4 P5 32.51(7) . . ? O5 P4 P5 106.40(6) . . ? Cl3 P4 P5 138.79(3) . . ? O6 P5 N5 108.06(9) . . ? O6 P5 N4 109.95(9) . . ? N5 P5 N4 117.63(10) . . ? O6 P5 Cl4 104.53(6) . . ? N5 P5 Cl4 108.25(8) . . ? N4 P5 Cl4 107.63(7) . . ? O6 P5 P4 102.92(6) . . ? N5 P5 P4 91.99(7) . . ? N4 P5 P4 32.50(7) . . ? Cl4 P5 P4 138.40(3) . . ? N5 P6 O7 105.18(9) . . ? N5 P6 O8 112.46(10) . . ? O7 P6 O8 102.84(8) . . ? N5 P6 N6 118.87(10) . . ? O7 P6 N6 111.04(10) . . ? O8 P6 N6 105.40(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.733 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.076