data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Besli, Serap' _publ_contact_author_email besli@gyte.edu.tr loop_ _publ_author_name S.Besli S.Coles D.Davies A.Kilic data_2b _database_code_depnum_ccdc_archive 'CCDC 778738' #TrackingRef '- CIF Files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 Cl6 N10 P6' _chemical_formula_weight 652.84 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5998(2) _cell_length_b 8.7747(2) _cell_length_c 9.4768(2) _cell_angle_alpha 114.0400(10) _cell_angle_beta 95.0370(10) _cell_angle_gamma 114.3700(10) _cell_volume 566.06(2) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2516 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 1.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7288 _exptl_absorpt_correction_T_max 0.7944 _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 12378 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2577 _reflns_number_gt 2456 _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^)+(0.0180P)^2^+0.5252P] 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 2577 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0222 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.2098(2) 0.3744(2) 0.0609(2) 0.0149(3) Uani 1 1 d . . . H1A H 0.2467 0.4316 -0.0086 0.022 Uiso 1 1 calc R . . H1B H 0.2916 0.4635 0.1720 0.022 Uiso 1 1 calc R . . H1C H 0.0874 0.3483 0.0605 0.022 Uiso 1 1 calc R . . C2 C 0.0866(2) 0.0371(2) -0.16166(19) 0.0127(3) Uani 1 1 d . . . H2A H -0.0307 0.0330 -0.1694 0.015 Uiso 1 1 calc R . . H2B H 0.0694 -0.0866 -0.1732 0.015 Uiso 1 1 calc R . . C3 C 0.1519(2) 0.0629(2) -0.3005(2) 0.0148(3) Uani 1 1 d . . . H3A H 0.1085 -0.0644 -0.3961 0.018 Uiso 1 1 calc R . . H3B H 0.1020 0.1317 -0.3324 0.018 Uiso 1 1 calc R . . C4 C 0.3566(2) 0.1762(2) -0.24759(19) 0.0108(3) Uani 1 1 d . . . H4A H 0.3975 0.1493 -0.3450 0.013 Uiso 1 1 calc R . . H4B H 0.3970 0.3151 -0.1886 0.013 Uiso 1 1 calc R . . N5 N 0.55997(17) -0.12586(18) 0.14047(15) 0.0084(3) Uani 1 1 d . . . N1 N 0.35222(17) 0.00025(18) 0.06607(15) 0.0085(3) Uani 1 1 d . . . N2 N 0.62031(18) 0.22303(18) 0.35456(16) 0.0110(3) Uani 1 1 d . . . N3 N 0.55139(18) 0.38394(18) 0.18237(16) 0.0100(3) Uani 1 1 d . . . N4 N 0.21538(17) 0.19431(18) -0.00098(16) 0.0097(3) Uani 1 1 d . . . P1 P 0.39589(5) 0.18004(5) 0.03869(4) 0.00671(9) Uani 1 1 d . . . P2 P 0.47173(5) 0.01459(5) 0.21134(4) 0.00679(9) Uani 1 1 d . . . P3 P 0.67694(5) 0.39968(5) 0.32482(5) 0.00796(9) Uani 1 1 d . . . Cl Cl 0.30611(5) -0.10990(5) 0.31722(5) 0.01257(9) Uani 1 1 d . . . Cl2 Cl 0.92691(5) 0.49002(6) 0.30403(5) 0.01635(10) Uani 1 1 d . . . Cl3 Cl 0.72532(5) 0.62911(5) 0.53189(4) 0.01340(9) 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 0.0178(8) 0.0144(8) 0.0170(8) 0.0067(7) 0.0065(7) 0.0125(7) C2 0.0089(7) 0.0126(7) 0.0121(7) 0.0050(6) -0.0007(6) 0.0033(6) C3 0.0139(8) 0.0166(8) 0.0116(7) 0.0067(6) 0.0005(6) 0.0065(7) C4 0.0143(8) 0.0124(7) 0.0097(7) 0.0076(6) 0.0034(6) 0.0078(6) N5 0.0119(6) 0.0101(6) 0.0073(6) 0.0057(5) 0.0037(5) 0.0074(5) N1 0.0088(6) 0.0074(6) 0.0080(6) 0.0039(5) 0.0016(5) 0.0031(5) N2 0.0130(7) 0.0080(6) 0.0075(6) 0.0022(5) -0.0006(5) 0.0037(5) N3 0.0117(6) 0.0066(6) 0.0098(6) 0.0034(5) 0.0013(5) 0.0039(5) N4 0.0095(6) 0.0100(6) 0.0100(6) 0.0040(5) 0.0024(5) 0.0062(5) P1 0.00765(19) 0.00616(18) 0.00636(18) 0.00288(15) 0.00190(14) 0.00365(15) P2 0.00817(19) 0.00679(18) 0.00587(18) 0.00336(15) 0.00257(14) 0.00373(15) P3 0.00786(19) 0.00643(18) 0.00682(18) 0.00181(15) 0.00134(14) 0.00281(15) Cl 0.01375(19) 0.01603(19) 0.01308(18) 0.01050(15) 0.00804(15) 0.00754(15) Cl2 0.00982(18) 0.0188(2) 0.0186(2) 0.00809(16) 0.00630(15) 0.00624(16) Cl3 0.01310(19) 0.00867(17) 0.00962(18) -0.00063(14) 0.00200(14) 0.00333(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 N4 1.4683(19) . ? C2 N4 1.4763(19) . ? C2 C3 1.538(2) . ? C3 C4 1.527(2) . ? C4 N5 1.4962(19) 2_655 ? N5 C4 1.4962(19) 2_655 ? N5 P2 1.6530(13) . ? N5 P1 1.6903(13) 2_655 ? N1 P2 1.5721(13) . ? N1 P1 1.5996(13) . ? N2 P3 1.5736(14) . ? N2 P2 1.6014(13) . ? N3 P3 1.5736(13) . ? N3 P1 1.6013(13) . ? N4 P1 1.6319(13) . ? P1 N5 1.6903(13) 2_655 ? P2 Cl 2.0220(5) . ? P3 Cl3 2.0059(5) . ? P3 Cl2 2.0208(6) . ? 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 111.75(13) . . ? C4 C3 C2 110.53(13) . . ? N5 C4 C3 111.85(13) 2_655 . ? C4 N5 P2 120.98(10) 2_655 . ? C4 N5 P1 114.96(10) 2_655 2_655 ? P2 N5 P1 122.69(8) . 2_655 ? P2 N1 P1 122.60(8) . . ? P3 N2 P2 118.87(8) . . ? P3 N3 P1 121.26(8) . . ? C1 N4 C2 116.41(13) . . ? C1 N4 P1 124.50(11) . . ? C2 N4 P1 112.31(10) . . ? N1 P1 N3 116.01(7) . . ? N1 P1 N4 110.99(7) . . ? N3 P1 N4 109.04(7) . . ? N1 P1 N5 106.44(7) . 2_655 ? N3 P1 N5 112.08(7) . 2_655 ? N4 P1 N5 101.28(7) . 2_655 ? N1 P2 N2 118.41(7) . . ? N1 P2 N5 109.75(7) . . ? N2 P2 N5 111.08(7) . . ? N1 P2 Cl 107.58(5) . . ? N2 P2 Cl 105.98(5) . . ? N5 P2 Cl 102.73(5) . . ? N3 P3 N2 119.69(7) . . ? N3 P3 Cl3 108.53(5) . . ? N2 P3 Cl3 108.81(5) . . ? N3 P3 Cl2 108.86(6) . . ? N2 P3 Cl2 109.74(6) . . ? Cl3 P3 Cl2 99.28(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.358 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.077 #===END data_4b _database_code_depnum_ccdc_archive 'CCDC 778739' #TrackingRef '- CIF Files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H14 Cl8 N8 P6' _chemical_formula_weight 667.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 11.6755(17) _cell_length_b 8.9298(13) _cell_length_c 23.758(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.549(2) _cell_angle_gamma 90.00 _cell_volume 2465.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5485 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.46 _exptl_crystal_description speck _exptl_crystal_colour colourless _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.67090 _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 ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 16848 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6499 _reflns_number_gt 5089 _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 ? _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^)+(0.0418P)^2^+27.5511P] 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 6499 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.1832 _refine_ls_wR_factor_gt 0.1749 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 0.8339(5) 0.3071(6) -0.0117(2) 0.0210(11) Uani 1 1 d . . . H1 H 0.7780 0.3353 -0.0445 0.025 Uiso 1 1 calc R . . C2 C 0.8894(6) 0.1561(7) -0.0251(3) 0.0342(15) Uani 1 1 d . . . H2A H 0.9324 0.1675 -0.0583 0.051 Uiso 1 1 calc R . . H2B H 0.8292 0.0804 -0.0330 0.051 Uiso 1 1 calc R . . H2C H 0.9420 0.1243 0.0073 0.051 Uiso 1 1 calc R . . C3 C 0.7692(6) 0.2976(8) 0.0406(3) 0.0308(14) Uani 1 1 d . . . H3A H 0.8212 0.2618 0.0726 0.046 Uiso 1 1 calc R . . H3B H 0.7046 0.2278 0.0336 0.046 Uiso 1 1 calc R . . H3C H 0.7400 0.3970 0.0493 0.046 Uiso 1 1 calc R . . C4 C 0.6609(5) -0.1936(7) -0.0125(2) 0.0210(11) Uani 1 1 d . . . H4 H 0.7052 -0.1620 -0.0444 0.025 Uiso 1 1 calc R . . C5 C 0.7436(6) -0.2061(9) 0.0400(3) 0.0345(15) Uani 1 1 d . . . H5A H 0.7742 -0.1068 0.0505 0.052 Uiso 1 1 calc R . . H5B H 0.8070 -0.2730 0.0327 0.052 Uiso 1 1 calc R . . H5C H 0.7033 -0.2467 0.0710 0.052 Uiso 1 1 calc R . . C6 C 0.6023(7) -0.3423(8) -0.0282(3) 0.0372(16) Uani 1 1 d . . . H6A H 0.5640 -0.3796 0.0040 0.056 Uiso 1 1 calc R . . H6B H 0.6601 -0.4151 -0.0378 0.056 Uiso 1 1 calc R . . H6C H 0.5453 -0.3277 -0.0608 0.056 Uiso 1 1 calc R . . N1 N 1.0458(5) 0.4010(6) 0.1845(2) 0.0237(10) Uani 1 1 d . . . N2 N 1.0937(4) 0.3386(5) 0.0772(2) 0.0186(9) Uani 1 1 d . . . N3 N 0.9600(4) 0.5737(5) 0.0970(2) 0.0187(9) Uani 1 1 d . . . N4 N 0.9229(4) 0.4255(5) -0.00405(19) 0.0168(9) Uani 1 1 d . . . N5 N 0.4340(4) -0.1619(5) 0.0760(2) 0.0192(9) Uani 1 1 d . . . N6 N 0.5144(4) -0.0974(6) 0.1847(2) 0.0215(10) Uani 1 1 d . . . N7 N 0.5793(4) 0.0680(6) 0.0976(2) 0.0208(10) Uani 1 1 d . . . N8 N 0.5737(4) -0.0766(5) -0.00429(19) 0.0165(9) Uani 1 1 d . . . P1 P 0.96648(13) 0.53493(17) 0.16158(6) 0.0184(3) Uani 1 1 d . . . P2 P 1.10306(13) 0.29592(17) 0.14166(6) 0.0188(3) Uani 1 1 d . . . P3 P 1.01512(12) 0.47357(16) 0.05114(6) 0.0153(3) Uani 1 1 d . . . P4 P 0.50475(12) -0.02804(16) 0.05096(6) 0.0158(3) Uani 1 1 d . . . P5 P 0.44055(13) -0.19900(16) 0.14089(6) 0.0181(3) Uani 1 1 d . . . P6 P 0.58932(12) 0.03410(17) 0.16260(6) 0.0178(3) Uani 1 1 d . . . Cl1 Cl 0.80819(15) 0.4994(2) 0.18460(8) 0.0382(4) Uani 1 1 d . . . Cl2 Cl 1.01203(14) 0.71714(17) 0.20664(6) 0.0267(3) Uani 1 1 d . . . Cl3 Cl 1.04303(16) 0.08707(17) 0.14910(7) 0.0312(3) Uani 1 1 d . . . Cl4 Cl 1.26816(14) 0.2685(2) 0.16935(7) 0.0352(4) Uani 1 1 d . . . Cl5 Cl 0.49361(17) -0.41089(18) 0.15240(7) 0.0345(4) Uani 1 1 d . . . Cl6 Cl 0.28118(13) -0.2114(2) 0.16371(7) 0.0348(4) Uani 1 1 d . . . Cl7 Cl 0.55516(13) 0.22217(17) 0.20312(6) 0.0258(3) Uani 1 1 d . . . Cl8 Cl 0.75361(13) -0.0005(2) 0.19142(7) 0.0336(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 0.023(3) 0.016(3) 0.023(3) 0.001(2) 0.000(2) -0.008(2) C2 0.042(4) 0.017(3) 0.042(4) -0.007(3) -0.004(3) -0.002(3) C3 0.027(3) 0.036(4) 0.030(3) 0.004(3) 0.005(2) -0.016(3) C4 0.023(3) 0.018(3) 0.022(3) -0.001(2) 0.004(2) 0.006(2) C5 0.031(3) 0.039(4) 0.033(3) 0.001(3) -0.002(3) 0.015(3) C6 0.042(4) 0.022(3) 0.047(4) -0.006(3) 0.000(3) 0.006(3) N1 0.036(3) 0.018(2) 0.018(2) 0.0009(19) 0.005(2) 0.007(2) N2 0.020(2) 0.015(2) 0.020(2) 0.0000(18) 0.0020(17) 0.0049(18) N3 0.019(2) 0.017(2) 0.021(2) -0.0008(18) 0.0051(17) 0.0025(18) N4 0.021(2) 0.012(2) 0.017(2) 0.0012(17) 0.0005(17) -0.0031(17) N5 0.022(2) 0.015(2) 0.021(2) -0.0005(18) 0.0019(18) -0.0046(18) N6 0.026(2) 0.018(2) 0.020(2) 0.0040(19) 0.0006(18) -0.0061(19) N7 0.021(2) 0.020(2) 0.021(2) 0.0032(19) 0.0029(18) -0.0054(19) N8 0.016(2) 0.017(2) 0.017(2) -0.0001(18) 0.0035(16) 0.0054(18) P1 0.0220(7) 0.0162(6) 0.0175(6) -0.0002(5) 0.0043(5) 0.0011(5) P2 0.0208(7) 0.0147(6) 0.0208(7) 0.0016(5) 0.0012(5) 0.0024(5) P3 0.0168(6) 0.0130(6) 0.0163(6) 0.0002(5) 0.0023(5) -0.0005(5) P4 0.0167(6) 0.0141(6) 0.0167(6) 0.0008(5) 0.0019(5) 0.0002(5) P5 0.0198(7) 0.0154(6) 0.0191(6) 0.0026(5) 0.0019(5) -0.0033(5) P6 0.0184(6) 0.0162(6) 0.0184(6) -0.0002(5) -0.0002(5) -0.0012(5) Cl1 0.0273(8) 0.0509(11) 0.0387(9) -0.0039(8) 0.0149(7) -0.0066(7) Cl2 0.0380(8) 0.0186(6) 0.0237(7) -0.0051(5) 0.0039(6) 0.0003(6) Cl3 0.0465(9) 0.0147(6) 0.0336(8) 0.0030(6) 0.0095(7) -0.0001(6) Cl4 0.0259(7) 0.0464(10) 0.0319(8) 0.0035(7) -0.0047(6) 0.0084(7) Cl5 0.0509(10) 0.0169(7) 0.0349(8) 0.0036(6) 0.0003(7) 0.0031(7) Cl6 0.0221(7) 0.0548(11) 0.0282(8) 0.0048(7) 0.0060(6) -0.0062(7) Cl7 0.0332(8) 0.0200(7) 0.0240(7) -0.0059(5) 0.0014(5) 0.0004(6) Cl8 0.0215(7) 0.0414(9) 0.0362(8) 0.0004(7) -0.0053(6) 0.0043(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 1.481(7) . ? C1 C3 1.517(8) . ? C1 C2 1.544(9) . ? C4 N8 1.485(7) . ? C4 C5 1.505(9) . ? C4 C6 1.523(9) . ? N1 P1 1.577(5) . ? N1 P2 1.580(5) . ? N2 P2 1.571(5) . ? N2 P3 1.603(5) . ? N3 P1 1.567(5) . ? N3 P3 1.593(5) . ? N4 P3 1.657(5) 3_765 ? N4 P3 1.670(5) . ? N5 P5 1.570(5) . ? N5 P4 1.600(5) . ? N6 P5 1.574(5) . ? N6 P6 1.585(5) . ? N7 P6 1.568(5) . ? N7 P4 1.591(5) . ? N8 P4 1.657(5) 3_655 ? N8 P4 1.662(4) . ? P1 Cl2 1.992(2) . ? P1 Cl1 2.003(2) . ? P2 Cl4 1.991(2) . ? P2 Cl3 2.006(2) . ? P3 N4 1.657(5) 3_765 ? P3 P3 2.467(3) 3_765 ? P4 N8 1.657(5) 3_655 ? P4 P4 2.465(3) 3_655 ? P5 Cl6 1.991(2) . ? P5 Cl5 2.001(2) . ? P6 Cl7 1.995(2) . ? P6 Cl8 1.998(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 C3 109.8(5) . . ? N4 C1 C2 110.2(5) . . ? C3 C1 C2 111.9(5) . . ? N8 C4 C5 109.7(5) . . ? N8 C4 C6 110.4(5) . . ? C5 C4 C6 112.0(6) . . ? P1 N1 P2 119.9(3) . . ? P2 N2 P3 122.9(3) . . ? P1 N3 P3 124.1(3) . . ? C1 N4 P3 130.8(4) . 3_765 ? C1 N4 P3 132.1(4) . . ? P3 N4 P3 95.7(2) 3_765 . ? P5 N5 P4 123.0(3) . . ? P5 N6 P6 119.5(3) . . ? P6 N7 P4 124.4(3) . . ? C4 N8 P4 130.6(4) . 3_655 ? C4 N8 P4 132.6(4) . . ? P4 N8 P4 95.9(2) 3_655 . ? N3 P1 N1 118.5(3) . . ? N3 P1 Cl2 109.3(2) . . ? N1 P1 Cl2 108.4(2) . . ? N3 P1 Cl1 110.1(2) . . ? N1 P1 Cl1 108.2(2) . . ? Cl2 P1 Cl1 100.84(9) . . ? N2 P2 N1 119.3(3) . . ? N2 P2 Cl4 109.02(19) . . ? N1 P2 Cl4 108.5(2) . . ? N2 P2 Cl3 108.6(2) . . ? N1 P2 Cl3 108.8(2) . . ? Cl4 P2 Cl3 101.06(10) . . ? N3 P3 N2 114.3(3) . . ? N3 P3 N4 112.9(2) . 3_765 ? N2 P3 N4 113.5(2) . 3_765 ? N3 P3 N4 114.1(3) . . ? N2 P3 N4 114.3(2) . . ? N4 P3 N4 84.3(2) 3_765 . ? N3 P3 P3 122.5(2) . 3_765 ? N2 P3 P3 123.16(19) . 3_765 ? N4 P3 P3 42.36(16) 3_765 3_765 ? N4 P3 P3 41.93(16) . 3_765 ? N7 P4 N5 114.3(3) . . ? N7 P4 N8 113.0(3) . 3_655 ? N5 P4 N8 113.5(3) . 3_655 ? N7 P4 N8 114.6(2) . . ? N5 P4 N8 114.0(3) . . ? N8 P4 N8 84.1(2) 3_655 . ? N7 P4 P4 122.9(2) . 3_655 ? N5 P4 P4 122.8(2) . 3_655 ? N8 P4 P4 42.13(15) 3_655 3_655 ? N8 P4 P4 41.96(16) . 3_655 ? N5 P5 N6 120.0(3) . . ? N5 P5 Cl6 108.7(2) . . ? N6 P5 Cl6 108.6(2) . . ? N5 P5 Cl5 108.6(2) . . ? N6 P5 Cl5 108.2(2) . . ? Cl6 P5 Cl5 101.26(10) . . ? N7 P6 N6 118.7(3) . . ? N7 P6 Cl7 108.3(2) . . ? N6 P6 Cl7 108.7(2) . . ? N7 P6 Cl8 110.2(2) . . ? N6 P6 Cl8 108.3(2) . . ? Cl7 P6 Cl8 101.24(9) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.037 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.164 #===END data_5b _database_code_depnum_ccdc_archive 'CCDC 778740' #TrackingRef '- CIF Files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Cl8 N8 O P6' _chemical_formula_weight 685.69 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 12.52630(10) _cell_length_b 12.4818(2) _cell_length_c 16.4619(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2573.83(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 1.267 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6873 _exptl_absorpt_correction_T_max 0.9874 _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 44787 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5883 _reflns_number_gt 5393 _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^)+(0.0222P)^2^+1.0101P] 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 0.03(5) _refine_ls_number_reflns 5883 _refine_ls_number_parameters 274 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.010 _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 0.0947(2) 0.7833(2) 0.36411(19) 0.0211(6) Uani 1 1 d . . . H1 H 0.0674 0.8553 0.3474 0.025 Uiso 1 1 calc R . . C2 C 0.0156(3) 0.7342(4) 0.4220(2) 0.0553(13) Uani 1 1 d . . . H2A H -0.0524 0.7227 0.3939 0.083 Uiso 1 1 calc R . . H2B H 0.0045 0.7825 0.4681 0.083 Uiso 1 1 calc R . . H2C H 0.0431 0.6654 0.4416 0.083 Uiso 1 1 calc R . . C3 C 0.2020(2) 0.7982(3) 0.4038(2) 0.0328(8) Uani 1 1 d . . . H3A H 0.2305 0.7282 0.4200 0.049 Uiso 1 1 calc R . . H3B H 0.1943 0.8438 0.4519 0.049 Uiso 1 1 calc R . . H3C H 0.2511 0.8322 0.3653 0.049 Uiso 1 1 calc R . . C4 C -0.1356(2) 0.8253(2) 0.02728(19) 0.0213(7) Uani 1 1 d . . . H4 H -0.0602 0.7991 0.0298 0.026 Uiso 1 1 calc R . . C5 C -0.2040(3) 0.7376(3) -0.0095(2) 0.0299(8) Uani 1 1 d . . . H5A H -0.1938 0.6710 0.0210 0.045 Uiso 1 1 calc R . . H5B H -0.1832 0.7265 -0.0663 0.045 Uiso 1 1 calc R . . H5C H -0.2793 0.7588 -0.0071 0.045 Uiso 1 1 calc R . . C6 C -0.1381(3) 0.9256(3) -0.0247(2) 0.0303(8) Uani 1 1 d . . . H6A H -0.2119 0.9507 -0.0300 0.045 Uiso 1 1 calc R . . H6B H -0.1093 0.9093 -0.0787 0.045 Uiso 1 1 calc R . . H6C H -0.0947 0.9815 0.0009 0.045 Uiso 1 1 calc R . . N1 N -0.07450(17) 0.50014(18) 0.12664(16) 0.0188(5) Uani 1 1 d . . . N2 N -0.08777(17) 0.65174(18) 0.24344(15) 0.0171(5) Uani 1 1 d . . . N3 N 0.08286(17) 0.64981(17) 0.14335(14) 0.0138(5) Uani 1 1 d . . . N4 N 0.10804(19) 0.71740(19) 0.29050(15) 0.0157(5) Uani 1 1 d . . . O5 O -0.00273(13) 0.82769(13) 0.19533(13) 0.0154(4) Uani 1 1 d . . . N5 N -0.04904(18) 1.01308(18) 0.15512(15) 0.0166(5) Uani 1 1 d . . . N6 N -0.13123(19) 1.12049(19) 0.28400(16) 0.0236(6) Uani 1 1 d . . . N7 N -0.17687(18) 0.90825(18) 0.26198(15) 0.0152(5) Uani 1 1 d . . . N8 N -0.17277(18) 0.84563(18) 0.11140(15) 0.0158(5) Uani 1 1 d . . . P1 P 0.03691(5) 0.54734(5) 0.09921(5) 0.01418(15) Uani 1 1 d . . . P2 P -0.13281(5) 0.54762(5) 0.20397(5) 0.01501(15) Uani 1 1 d . . . P3 P 0.02302(5) 0.70526(5) 0.21812(5) 0.01333(15) Uani 1 1 d . . . P4 P -0.10439(5) 0.90278(5) 0.18139(5) 0.01314(15) Uani 1 1 d . . . P5 P -0.06308(5) 1.12022(5) 0.20279(5) 0.01641(16) Uani 1 1 d . . . P6 P -0.19066(5) 1.01525(6) 0.31157(5) 0.01658(16) Uani 1 1 d . . . Cl1 Cl 0.14571(5) 0.42960(5) 0.10168(5) 0.02242(16) Uani 1 1 d . . . Cl2 Cl 0.03138(5) 0.57591(6) -0.02021(4) 0.02361(16) Uani 1 1 d . . . Cl3 Cl -0.14264(6) 0.43171(6) 0.28836(5) 0.02498(17) Uani 1 1 d . . . Cl4 Cl -0.28584(5) 0.56622(6) 0.17575(5) 0.02509(17) Uani 1 1 d . . . Cl5 Cl -0.12254(6) 1.23218(6) 0.12888(5) 0.02780(17) Uani 1 1 d . . . Cl6 Cl 0.07950(6) 1.18379(6) 0.22921(6) 0.0312(2) Uani 1 1 d . . . Cl7 Cl -0.34695(5) 1.04811(6) 0.32032(5) 0.02577(18) Uani 1 1 d . . . Cl8 Cl -0.15422(7) 0.98853(6) 0.42810(5) 0.03039(18) Uani 1 1 d . . . H8N H -0.239(3) 0.845(2) 0.117(2) 0.023(9) Uiso 1 1 d . . . H4N H 0.162(3) 0.694(3) 0.280(2) 0.028(10) 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 0.0288(16) 0.0225(17) 0.0118(16) -0.0032(13) -0.0019(12) 0.0089(12) C2 0.034(2) 0.115(4) 0.017(2) -0.022(2) 0.0043(15) -0.024(2) C3 0.0305(17) 0.042(2) 0.026(2) -0.0114(17) 0.0017(14) -0.0105(14) C4 0.0197(14) 0.0261(17) 0.0182(18) -0.0049(14) -0.0008(12) 0.0046(11) C5 0.0352(19) 0.0280(19) 0.026(2) -0.0108(15) -0.0067(14) -0.0004(13) C6 0.0368(18) 0.0331(19) 0.0211(19) -0.0005(15) 0.0002(15) -0.0006(14) N1 0.0162(12) 0.0173(12) 0.0227(15) -0.0085(11) -0.0001(10) -0.0045(9) N2 0.0158(12) 0.0153(12) 0.0202(14) -0.0046(11) 0.0043(9) -0.0030(9) N3 0.0129(11) 0.0132(12) 0.0153(14) -0.0023(10) 0.0017(9) -0.0024(9) N4 0.0123(12) 0.0196(13) 0.0151(14) -0.0043(11) -0.0001(10) 0.0043(9) O5 0.0112(8) 0.0107(9) 0.0244(13) -0.0006(9) -0.0007(8) -0.0014(7) N5 0.0181(11) 0.0123(12) 0.0193(15) -0.0035(10) 0.0032(9) -0.0025(9) N6 0.0353(14) 0.0135(13) 0.0219(15) -0.0045(11) 0.0099(11) -0.0052(10) N7 0.0173(12) 0.0125(12) 0.0157(13) -0.0034(10) 0.0040(9) -0.0023(9) N8 0.0099(12) 0.0201(12) 0.0174(15) -0.0042(11) 0.0013(10) -0.0011(9) P1 0.0134(3) 0.0142(4) 0.0149(4) -0.0025(3) 0.0006(3) 0.0001(3) P2 0.0125(3) 0.0143(3) 0.0182(4) -0.0009(3) 0.0017(3) -0.0014(2) P3 0.0119(3) 0.0124(3) 0.0156(4) -0.0017(3) 0.0012(3) -0.0004(2) P4 0.0119(3) 0.0108(3) 0.0167(4) -0.0020(3) 0.0012(3) 0.0004(2) P5 0.0194(3) 0.0110(3) 0.0188(4) -0.0015(3) 0.0019(3) -0.0018(3) P6 0.0199(4) 0.0143(4) 0.0156(4) -0.0021(3) 0.0025(3) -0.0002(3) Cl1 0.0208(3) 0.0170(4) 0.0294(4) -0.0029(3) 0.0008(3) 0.0051(3) Cl2 0.0259(4) 0.0303(4) 0.0146(4) -0.0021(3) -0.0009(3) -0.0004(3) Cl3 0.0313(4) 0.0208(4) 0.0228(4) 0.0050(3) -0.0006(3) -0.0054(3) Cl4 0.0118(3) 0.0263(4) 0.0372(5) -0.0014(4) -0.0019(3) -0.0005(3) Cl5 0.0398(4) 0.0158(4) 0.0278(5) 0.0025(3) -0.0004(3) 0.0046(3) Cl6 0.0251(4) 0.0251(4) 0.0434(6) -0.0075(4) -0.0018(3) -0.0099(3) Cl7 0.0219(4) 0.0238(4) 0.0317(5) -0.0093(3) 0.0050(3) 0.0037(3) Cl8 0.0442(4) 0.0299(4) 0.0170(4) -0.0012(4) -0.0038(3) 0.0009(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 1.474(4) . ? C1 C2 1.505(5) . ? C1 C3 1.506(4) . ? C1 H1 1.0000 . ? 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 N8 1.483(4) . ? C4 C6 1.517(4) . ? C4 C5 1.517(4) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? N1 P1 1.581(2) . ? N1 P2 1.583(3) . ? N2 P2 1.559(2) . ? N2 P3 1.596(2) . ? N3 P1 1.580(2) . ? N3 P3 1.599(2) . ? N4 P3 1.605(2) . ? N4 H4N 0.76(3) . ? O5 P4 1.5978(17) . ? O5 P3 1.6062(18) . ? N5 P5 1.560(2) . ? N5 P4 1.601(2) . ? N6 P6 1.577(2) . ? N6 P5 1.586(3) . ? N7 P6 1.575(2) . ? N7 P4 1.609(2) . ? N8 P4 1.603(2) . ? N8 H8N 0.83(3) . ? P1 Cl2 1.9992(11) . ? P1 Cl1 2.0048(9) . ? P2 Cl4 1.9859(9) . ? P2 Cl3 2.0096(10) . ? P5 Cl5 1.9969(11) . ? P5 Cl6 2.0021(10) . ? P6 Cl8 1.9997(11) . ? P6 Cl7 2.0054(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 C1 C2 111.6(3) . . ? N4 C1 C3 108.9(2) . . ? C2 C1 C3 111.3(3) . . ? N4 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? C3 C1 H1 108.3 . . ? 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 . . ? N8 C4 C6 112.3(2) . . ? N8 C4 C5 108.6(2) . . ? C6 C4 C5 111.0(3) . . ? N8 C4 H4 108.3 . . ? C6 C4 H4 108.3 . . ? C5 C4 H4 108.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? P1 N1 P2 119.84(14) . . ? P2 N2 P3 123.71(15) . . ? P1 N3 P3 122.26(14) . . ? C1 N4 P3 125.99(19) . . ? C1 N4 H4N 120(3) . . ? P3 N4 H4N 113(3) . . ? P4 O5 P3 138.74(11) . . ? P5 N5 P4 123.53(15) . . ? P6 N6 P5 119.67(15) . . ? P6 N7 P4 121.69(14) . . ? C4 N8 P4 125.40(19) . . ? C4 N8 H8N 114(2) . . ? P4 N8 H8N 117(2) . . ? N3 P1 N1 119.48(12) . . ? N3 P1 Cl2 108.69(10) . . ? N1 P1 Cl2 108.47(10) . . ? N3 P1 Cl1 109.66(9) . . ? N1 P1 Cl1 108.74(9) . . ? Cl2 P1 Cl1 100.04(4) . . ? N2 P2 N1 118.72(12) . . ? N2 P2 Cl4 110.45(9) . . ? N1 P2 Cl4 107.52(9) . . ? N2 P2 Cl3 109.53(10) . . ? N1 P2 Cl3 108.34(10) . . ? Cl4 P2 Cl3 100.76(4) . . ? N2 P3 N3 115.33(12) . . ? N2 P3 N4 115.00(13) . . ? N3 P3 N4 107.53(12) . . ? N2 P3 O5 106.54(11) . . ? N3 P3 O5 109.04(12) . . ? N4 P3 O5 102.52(11) . . ? O5 P4 N5 101.43(11) . . ? O5 P4 N8 105.55(11) . . ? N5 P4 N8 114.83(13) . . ? O5 P4 N7 110.87(12) . . ? N5 P4 N7 115.51(12) . . ? N8 P4 N7 108.06(12) . . ? N5 P5 N6 119.10(13) . . ? N5 P5 Cl5 109.60(10) . . ? N6 P5 Cl5 108.13(10) . . ? N5 P5 Cl6 110.38(9) . . ? N6 P5 Cl6 107.22(10) . . ? Cl5 P5 Cl6 100.82(4) . . ? N7 P6 N6 120.36(13) . . ? N7 P6 Cl8 109.32(10) . . ? N6 P6 Cl8 107.90(11) . . ? N7 P6 Cl7 108.53(9) . . ? N6 P6 Cl7 108.14(10) . . ? Cl8 P6 Cl7 100.84(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.333 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.075 #===END data_5c _database_code_depnum_ccdc_archive 'CCDC 778741' #TrackingRef '- CIF Files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl8 N8 O P6' _chemical_formula_weight 753.72 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 Cc 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' _cell_length_a 14.6358(2) _cell_length_b 16.3497(2) _cell_length_c 12.34480(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.4550(10) _cell_angle_gamma 90.00 _cell_volume 2817.98(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3334 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5931 _exptl_absorpt_correction_T_max 0.9884 _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 23887 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6203 _reflns_number_gt 5903 _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^)+(0.0000P)^2^+3.1530P] 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 0.24(5) _refine_ls_number_reflns 6203 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H4N H 0.308(2) 0.455(2) 0.818(3) 0.019(8) Uiso 1 1 d . . . H5N H 0.127(3) 0.562(2) 1.168(3) 0.039(12) Uiso 1 1 d . . . C1 C 0.41179(19) 0.51481(16) 0.9129(2) 0.0149(5) Uani 1 1 d . . . C2 C 0.4570(2) 0.5225(2) 0.8296(3) 0.0235(6) Uani 1 1 d . . . H2 H 0.4268 0.5024 0.7553 0.028 Uiso 1 1 calc R . . C3 C 0.5461(2) 0.5594(2) 0.8545(3) 0.0273(7) Uani 1 1 d . . . H3 H 0.5767 0.5640 0.7969 0.033 Uiso 1 1 calc R . . C4 C 0.5912(2) 0.58961(19) 0.9623(3) 0.0267(7) Uani 1 1 d . . . H4 H 0.6521 0.6153 0.9790 0.032 Uiso 1 1 calc R . . C5 C 0.5455(2) 0.5815(2) 1.0449(3) 0.0290(7) Uani 1 1 d . . . H5 H 0.5759 0.6017 1.1191 0.035 Uiso 1 1 calc R . . C6 C 0.4562(2) 0.54450(19) 1.0220(3) 0.0241(6) Uani 1 1 d . . . H6 H 0.4258 0.5395 1.0798 0.029 Uiso 1 1 calc R . . C7 C 0.01593(19) 0.55550(16) 1.0364(2) 0.0146(5) Uani 1 1 d . . . C8 C -0.0169(2) 0.57162(17) 0.9202(2) 0.0190(6) Uani 1 1 d . . . H8 H 0.0262 0.5901 0.8812 0.023 Uiso 1 1 calc R . . C9 C -0.1138(2) 0.56032(17) 0.8618(3) 0.0221(7) Uani 1 1 d . . . H9 H -0.1368 0.5712 0.7826 0.027 Uiso 1 1 calc R . . C10 C -0.1763(2) 0.53345(19) 0.9187(3) 0.0272(7) Uani 1 1 d . . . H10 H -0.2421 0.5258 0.8785 0.033 Uiso 1 1 calc R . . C11 C -0.1438(2) 0.5179(2) 1.0326(3) 0.0309(7) Uani 1 1 d . . . H11 H -0.1874 0.4998 1.0712 0.037 Uiso 1 1 calc R . . C12 C -0.0474(2) 0.52832(19) 1.0928(3) 0.0226(6) Uani 1 1 d . . . H12 H -0.0252 0.5169 1.1719 0.027 Uiso 1 1 calc R . . N1 N 0.16011(18) 0.30046(14) 1.0073(2) 0.0191(5) Uani 1 1 d . . . N2 N 0.27917(17) 0.43018(14) 1.07434(19) 0.0167(5) Uani 1 1 d . . . N3 N 0.14872(16) 0.42941(13) 0.86484(18) 0.0134(5) Uani 1 1 d . . . N4 N 0.32137(16) 0.47488(14) 0.8835(2) 0.0152(5) Uani 1 1 d . . . N5 N 0.11426(16) 0.56584(14) 1.1005(2) 0.0146(5) Uani 1 1 d . . . N6 N 0.28433(16) 0.63145(14) 1.17060(18) 0.0139(5) Uani 1 1 d . . . N7 N 0.27790(19) 0.79674(14) 1.1380(2) 0.0208(5) Uani 1 1 d . . . N8 N 0.14923(17) 0.69883(14) 0.99153(19) 0.0168(5) Uani 1 1 d . . . O1 O 0.22252(14) 0.56439(11) 0.96909(16) 0.0140(4) Uani 1 1 d . . . P1 P 0.10502(5) 0.34629(4) 0.89421(6) 0.01350(14) Uani 1 1 d . . . P2 P 0.24002(5) 0.34554(4) 1.10348(6) 0.01608(15) Uani 1 1 d . . . P3 P 0.24224(5) 0.46966(4) 0.95141(6) 0.01219(14) Uani 1 1 d . . . P4 P 0.19330(5) 0.61922(4) 1.06126(6) 0.01204(14) Uani 1 1 d . . . P5 P 0.32948(5) 0.71958(4) 1.20670(6) 0.01520(15) Uani 1 1 d . . . P6 P 0.19055(5) 0.78682(4) 1.02583(6) 0.01663(15) Uani 1 1 d . . . Cl1 Cl 0.08898(5) 0.26874(4) 0.76443(6) 0.01843(14) Uani 1 1 d . . . Cl2 Cl -0.03083(5) 0.36276(4) 0.89054(6) 0.02317(16) Uani 1 1 d . . . Cl3 Cl 0.19329(7) 0.35885(5) 1.23845(7) 0.0333(2) Uani 1 1 d . . . Cl4 Cl 0.34750(6) 0.26708(5) 1.16167(7) 0.0368(2) Uani 1 1 d . . . Cl5 Cl 0.34425(5) 0.73572(4) 1.37120(5) 0.02168(15) Uani 1 1 d . . . Cl6 Cl 0.46615(6) 0.72108(5) 1.20837(7) 0.03142(19) Uani 1 1 d . . . Cl7 Cl 0.08657(6) 0.86224(5) 1.03655(7) 0.02958(18) Uani 1 1 d . . . Cl8 Cl 0.22617(6) 0.83622(5) 0.89562(6) 0.02945(18) 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 0.0123(13) 0.0127(13) 0.0203(14) 0.0007(10) 0.0059(10) 0.0007(10) C2 0.0200(15) 0.0325(17) 0.0176(15) 0.0013(12) 0.0049(11) -0.0003(13) C3 0.0187(15) 0.0362(18) 0.0304(17) 0.0058(14) 0.0125(13) -0.0022(13) C4 0.0157(15) 0.0201(16) 0.045(2) -0.0056(14) 0.0109(13) -0.0058(12) C5 0.0156(15) 0.0334(18) 0.0369(19) -0.0170(14) 0.0062(13) -0.0042(13) C6 0.0188(15) 0.0296(16) 0.0252(16) -0.0106(13) 0.0087(12) -0.0068(13) C7 0.0138(13) 0.0095(12) 0.0199(14) -0.0022(10) 0.0041(10) -0.0014(10) C8 0.0180(14) 0.0147(14) 0.0227(15) -0.0001(11) 0.0039(11) -0.0005(11) C9 0.0208(15) 0.0141(14) 0.0256(16) -0.0007(11) -0.0022(12) 0.0049(11) C10 0.0104(14) 0.0254(17) 0.042(2) -0.0066(13) 0.0020(12) 0.0003(12) C11 0.0194(16) 0.0372(19) 0.041(2) -0.0064(15) 0.0166(14) -0.0105(14) C12 0.0204(15) 0.0293(17) 0.0180(15) -0.0018(12) 0.0056(12) -0.0052(12) N1 0.0260(13) 0.0119(11) 0.0177(12) 0.0015(9) 0.0040(10) -0.0066(10) N2 0.0176(12) 0.0176(12) 0.0133(11) 0.0026(9) 0.0021(9) -0.0023(10) N3 0.0131(11) 0.0137(11) 0.0116(11) -0.0010(8) 0.0006(9) -0.0015(9) N4 0.0147(12) 0.0159(12) 0.0149(12) -0.0048(9) 0.0043(9) -0.0036(9) N5 0.0150(12) 0.0160(12) 0.0132(12) 0.0011(9) 0.0048(9) -0.0005(9) N6 0.0134(11) 0.0135(11) 0.0126(11) 0.0002(8) 0.0004(9) 0.0002(9) N7 0.0276(14) 0.0111(11) 0.0188(12) -0.0002(9) -0.0007(10) -0.0030(10) N8 0.0180(12) 0.0141(11) 0.0160(12) 0.0001(9) 0.0017(9) 0.0000(9) O1 0.0179(9) 0.0094(8) 0.0157(10) 0.0000(7) 0.0064(7) -0.0002(7) P1 0.0135(3) 0.0120(3) 0.0150(3) -0.0017(3) 0.0042(3) -0.0028(3) P2 0.0202(4) 0.0143(3) 0.0128(3) 0.0016(3) 0.0036(3) -0.0007(3) P3 0.0124(3) 0.0120(3) 0.0119(3) -0.0003(2) 0.0032(2) -0.0014(3) P4 0.0121(3) 0.0109(3) 0.0126(3) -0.0009(2) 0.0030(2) -0.0011(3) P5 0.0148(3) 0.0145(3) 0.0153(3) -0.0018(3) 0.0030(3) -0.0032(3) P6 0.0221(4) 0.0109(3) 0.0160(4) 0.0003(3) 0.0043(3) -0.0012(3) Cl1 0.0203(3) 0.0174(3) 0.0178(3) -0.0053(3) 0.0060(2) -0.0042(3) Cl2 0.0151(3) 0.0224(4) 0.0346(4) -0.0064(3) 0.0113(3) -0.0038(3) Cl3 0.0556(6) 0.0294(4) 0.0214(4) -0.0054(3) 0.0213(4) -0.0151(4) Cl4 0.0322(5) 0.0299(4) 0.0402(5) 0.0135(3) -0.0012(4) 0.0106(4) Cl5 0.0286(4) 0.0188(3) 0.0153(3) -0.0032(3) 0.0031(3) -0.0037(3) Cl6 0.0185(4) 0.0355(5) 0.0426(5) -0.0111(3) 0.0126(3) -0.0098(3) Cl7 0.0365(5) 0.0196(4) 0.0314(4) 0.0006(3) 0.0084(3) 0.0111(3) Cl8 0.0373(4) 0.0291(4) 0.0221(4) 0.0049(3) 0.0091(3) -0.0123(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 C2 1.385(4) . ? C1 C6 1.395(4) . ? C1 N4 1.422(3) . ? C2 C3 1.385(4) . ? C3 C4 1.387(5) . ? C4 C5 1.384(5) . ? C5 C6 1.391(4) . ? C7 C12 1.390(4) . ? C7 C8 1.394(4) . ? C7 N5 1.429(3) . ? C8 C9 1.398(4) . ? C9 C10 1.382(5) . ? C10 C11 1.367(5) . ? C11 C12 1.394(4) . ? N1 P1 1.576(2) . ? N1 P2 1.577(2) . ? N2 P2 1.580(2) . ? N2 P3 1.587(2) . ? N3 P1 1.589(2) . ? N3 P3 1.603(2) . ? N4 P3 1.623(2) . ? N5 P4 1.634(2) . ? N6 P5 1.592(2) . ? N6 P4 1.599(2) . ? N7 P5 1.580(2) . ? N7 P6 1.586(2) . ? N8 P6 1.569(2) . ? N8 P4 1.587(2) . ? O1 P3 1.6023(19) . ? O1 P4 1.604(2) . ? P1 Cl2 1.9935(10) . ? P1 Cl1 2.0009(9) . ? P2 Cl4 1.9895(11) . ? P2 Cl3 1.9937(11) . ? P5 Cl5 1.9942(10) . ? P5 Cl6 1.9943(10) . ? P6 Cl7 1.9938(11) . ? P6 Cl8 2.0027(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.8(3) . . ? C2 C1 N4 117.9(2) . . ? C6 C1 N4 122.3(3) . . ? C1 C2 C3 120.2(3) . . ? C2 C3 C4 120.9(3) . . ? C5 C4 C3 118.4(3) . . ? C4 C5 C6 121.7(3) . . ? C5 C6 C1 118.9(3) . . ? C12 C7 C8 120.1(3) . . ? C12 C7 N5 118.2(3) . . ? C8 C7 N5 121.7(3) . . ? C7 C8 C9 119.3(3) . . ? C10 C9 C8 120.3(3) . . ? C11 C10 C9 120.2(3) . . ? C10 C11 C12 120.7(3) . . ? C7 C12 C11 119.5(3) . . ? P1 N1 P2 120.76(14) . . ? P2 N2 P3 122.08(15) . . ? P1 N3 P3 121.35(14) . . ? C1 N4 P3 130.2(2) . . ? C7 N5 P4 125.7(2) . . ? P5 N6 P4 121.34(14) . . ? P5 N7 P6 121.14(15) . . ? P6 N8 P4 123.01(15) . . ? P3 O1 P4 137.22(13) . . ? N1 P1 N3 118.32(12) . . ? N1 P1 Cl2 109.03(10) . . ? N3 P1 Cl2 110.25(9) . . ? N1 P1 Cl1 108.29(10) . . ? N3 P1 Cl1 108.53(9) . . ? Cl2 P1 Cl1 100.99(4) . . ? N1 P2 N2 118.39(12) . . ? N1 P2 Cl4 107.34(10) . . ? N2 P2 Cl4 110.21(10) . . ? N1 P2 Cl3 108.51(10) . . ? N2 P2 Cl3 109.47(10) . . ? Cl4 P2 Cl3 101.60(5) . . ? N2 P3 O1 106.64(12) . . ? N2 P3 N3 116.62(12) . . ? O1 P3 N3 109.57(11) . . ? N2 P3 N4 115.10(13) . . ? O1 P3 N4 101.84(11) . . ? N3 P3 N4 106.01(12) . . ? N8 P4 N6 117.09(12) . . ? N8 P4 O1 103.01(12) . . ? N6 P4 O1 109.67(12) . . ? N8 P4 N5 112.96(13) . . ? N6 P4 N5 107.54(12) . . ? O1 P4 N5 105.94(11) . . ? N7 P5 N6 118.75(13) . . ? N7 P5 Cl5 109.22(10) . . ? N6 P5 Cl5 108.29(9) . . ? N7 P5 Cl6 108.18(11) . . ? N6 P5 Cl6 110.17(9) . . ? Cl5 P5 Cl6 100.71(4) . . ? N8 P6 N7 118.28(12) . . ? N8 P6 Cl7 110.18(10) . . ? N7 P6 Cl7 108.07(10) . . ? N8 P6 Cl8 108.98(9) . . ? N7 P6 Cl8 108.90(11) . . ? Cl7 P6 Cl8 101.04(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.352 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.072 #===END data_6a _database_code_depnum_ccdc_archive 'CCDC 778742' #TrackingRef '- CIF Files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H6 Cl9 N7 O P6' _chemical_formula_weight 661.02 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 8.29070(10) _cell_length_b 8.95560(10) _cell_length_c 15.00720(10) _cell_angle_alpha 95.4020(10) _cell_angle_beta 95.1100(10) _cell_angle_gamma 101.3340(10) _cell_volume 1081.050(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 34900 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8546 _exptl_absorpt_correction_T_max 0.8546 _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 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 23785 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4968 _reflns_number_gt 4783 _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^)+(0.0359P)^2^+0.5884P] 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 4968 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0233 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_restrained_S_all 1.235 _refine_ls_shift/su_max 0.005 _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 0.6886(2) 0.0162(2) 0.10059(12) 0.0165(3) Uani 1 1 d . . . H1A H 0.7691 0.0620 0.1535 0.020 Uiso 1 1 calc R . . H1B H 0.7501 0.0082 0.0473 0.020 Uiso 1 1 calc R . . C2 C 0.5985(2) -0.1409(2) 0.11640(12) 0.0165(3) Uani 1 1 d . . . H2A H 0.6798 -0.2070 0.1258 0.020 Uiso 1 1 calc R . . H2B H 0.5217 -0.1872 0.0622 0.020 Uiso 1 1 calc R . . C3 C 0.5013(2) -0.1357(2) 0.19745(12) 0.0146(3) Uani 1 1 d . . . H3A H 0.4430 -0.2407 0.2048 0.018 Uiso 1 1 calc R . . H3B H 0.5783 -0.0956 0.2525 0.018 Uiso 1 1 calc R . . N1 N 0.55555(19) 0.24277(17) 0.24590(10) 0.0157(3) Uani 1 1 d . . . N2 N 0.38470(19) 0.46916(17) 0.22698(11) 0.0187(3) Uani 1 1 d . . . N3 N 0.30421(18) 0.20641(16) 0.11091(10) 0.0143(3) Uani 1 1 d . . . N4 N 0.37685(17) -0.03468(16) 0.18549(10) 0.0127(3) Uani 1 1 d . . . N5 N 0.1240(2) 0.04964(19) 0.26091(11) 0.0219(3) Uani 1 1 d . . . N6 N 0.0706(2) -0.09804(18) 0.40921(10) 0.0186(3) Uani 1 1 d . . . N7 N 0.18274(19) -0.23781(17) 0.26610(10) 0.0162(3) Uani 1 1 d . . . O1 O 0.56813(15) 0.11344(14) 0.08580(8) 0.0148(2) Uani 1 1 d . . . P1 P 0.45007(5) 0.14100(5) 0.15872(3) 0.01154(10) Uani 1 1 d . . . P2 P 0.54551(5) 0.41558(5) 0.26566(3) 0.01297(10) Uani 1 1 d . . . P3 P 0.27172(5) 0.36948(5) 0.14298(3) 0.01349(10) Uani 1 1 d . . . P4 P 0.18755(5) -0.09105(5) 0.21385(3) 0.01326(10) Uani 1 1 d . . . P5 P 0.07357(5) 0.05120(5) 0.35985(3) 0.01384(10) Uani 1 1 d . . . P6 P 0.16659(6) -0.22170(5) 0.37032(3) 0.01482(10) Uani 1 1 d . . . Cl1 Cl 0.58490(6) 0.47538(5) 0.39800(3) 0.02256(11) Uani 1 1 d . . . Cl2 Cl 0.74320(5) 0.55172(5) 0.22510(3) 0.02213(11) Uani 1 1 d . . . Cl3 Cl 0.28313(6) 0.49246(5) 0.03765(3) 0.02479(11) Uani 1 1 d . . . Cl4 Cl 0.03662(5) 0.35477(5) 0.16431(3) 0.02323(11) Uani 1 1 d . . . Cl5 Cl 0.04453(6) -0.16283(6) 0.09643(3) 0.02379(11) Uani 1 1 d . . . Cl6 Cl 0.22045(6) 0.22899(6) 0.43671(4) 0.02738(12) Uani 1 1 d . . . Cl7 Cl -0.14531(5) 0.10992(6) 0.36095(3) 0.02228(11) Uani 1 1 d . . . Cl8 Cl 0.39325(6) -0.18348(6) 0.43910(3) 0.02761(12) Uani 1 1 d . . . Cl9 Cl 0.06344(6) -0.42359(5) 0.40448(3) 0.02345(11) 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 0.0150(8) 0.0171(8) 0.0198(8) 0.0046(7) 0.0052(6) 0.0064(7) C2 0.0189(8) 0.0128(8) 0.0200(8) 0.0037(7) 0.0047(7) 0.0068(7) C3 0.0149(8) 0.0124(8) 0.0185(8) 0.0050(6) 0.0020(6) 0.0062(6) N1 0.0192(7) 0.0116(7) 0.0156(7) -0.0011(5) -0.0031(6) 0.0049(6) N2 0.0166(7) 0.0140(7) 0.0244(8) -0.0042(6) -0.0028(6) 0.0060(6) N3 0.0163(7) 0.0108(7) 0.0158(7) 0.0012(5) -0.0002(5) 0.0039(5) N4 0.0128(7) 0.0092(6) 0.0173(7) 0.0024(5) 0.0032(5) 0.0038(5) N5 0.0353(9) 0.0188(8) 0.0190(8) 0.0083(6) 0.0144(7) 0.0154(7) N6 0.0240(8) 0.0190(8) 0.0153(7) 0.0044(6) 0.0069(6) 0.0073(6) N7 0.0214(8) 0.0117(7) 0.0173(7) 0.0035(6) 0.0071(6) 0.0042(6) O1 0.0182(6) 0.0124(6) 0.0156(6) 0.0041(5) 0.0047(5) 0.0053(5) P1 0.0144(2) 0.0083(2) 0.0120(2) 0.00096(15) 0.00103(16) 0.00287(16) P2 0.0139(2) 0.0102(2) 0.0143(2) -0.00073(16) 0.00022(16) 0.00282(16) P3 0.0129(2) 0.0101(2) 0.0178(2) 0.00152(16) 0.00053(16) 0.00345(16) P4 0.0155(2) 0.0128(2) 0.0131(2) 0.00289(16) 0.00466(16) 0.00476(16) P5 0.0149(2) 0.0147(2) 0.0134(2) 0.00197(16) 0.00387(16) 0.00517(17) P6 0.0164(2) 0.0131(2) 0.0158(2) 0.00487(17) 0.00328(16) 0.00303(17) Cl1 0.0261(2) 0.0230(2) 0.0153(2) -0.00533(17) 0.00123(17) 0.00110(18) Cl2 0.0179(2) 0.0202(2) 0.0291(2) 0.00946(18) 0.00479(17) 0.00182(17) Cl3 0.0316(3) 0.0186(2) 0.0266(2) 0.01092(18) 0.00274(19) 0.00746(19) Cl4 0.0133(2) 0.0220(2) 0.0351(3) 0.00235(19) 0.00338(17) 0.00557(17) Cl5 0.0171(2) 0.0329(3) 0.0188(2) 0.00222(18) -0.00111(16) 0.00059(18) Cl6 0.0224(2) 0.0209(2) 0.0344(3) -0.00468(19) -0.00165(19) -0.00014(18) Cl7 0.0167(2) 0.0336(3) 0.0188(2) 0.00051(18) 0.00208(16) 0.01185(18) Cl8 0.0212(2) 0.0285(3) 0.0316(3) 0.0031(2) -0.00568(19) 0.00523(19) Cl9 0.0299(2) 0.0168(2) 0.0242(2) 0.00986(17) 0.00663(18) 0.00104(18) _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 1.464(2) . ? C1 C2 1.508(2) . ? C2 C3 1.520(2) . ? C3 N4 1.510(2) . ? N1 P2 1.5680(15) . ? N1 P1 1.6018(15) . ? N2 P2 1.5845(15) . ? N2 P3 1.5851(15) . ? N3 P3 1.5755(14) . ? N3 P1 1.5885(15) . ? N4 P4 1.6574(15) . ? N4 P1 1.6711(15) . ? N5 P5 1.5775(16) . ? N5 P4 1.5887(16) . ? N6 P5 1.5850(16) . ? N6 P6 1.5837(16) . ? N7 P6 1.5771(15) . ? N7 P4 1.5884(15) . ? O1 P1 1.5656(13) . ? P2 Cl1 1.9883(6) . ? P2 Cl2 2.0187(6) . ? P3 Cl4 1.9842(6) . ? P3 Cl3 2.0085(6) . ? P4 Cl5 2.0097(6) . ? P5 Cl7 1.9871(6) . ? P5 Cl6 1.9976(7) . ? P6 Cl9 1.9769(6) . ? P6 Cl8 2.0122(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 109.11(14) . . ? C1 C2 C3 112.24(14) . . ? N4 C3 C2 110.50(14) . . ? P2 N1 P1 119.72(9) . . ? P2 N2 P3 118.98(9) . . ? P3 N3 P1 121.85(9) . . ? C3 N4 P4 119.49(11) . . ? C3 N4 P1 116.21(11) . . ? P4 N4 P1 123.63(9) . . ? P5 N5 P4 121.53(10) . . ? P5 N6 P6 118.08(10) . . ? P6 N7 P4 118.79(9) . . ? C1 O1 P1 120.37(11) . . ? O1 P1 N3 106.98(7) . . ? O1 P1 N1 109.52(8) . . ? N3 P1 N1 117.13(8) . . ? O1 P1 N4 103.69(7) . . ? N3 P1 N4 109.91(8) . . ? N1 P1 N4 108.77(8) . . ? N1 P2 N2 118.80(8) . . ? N1 P2 Cl1 108.75(6) . . ? N2 P2 Cl1 109.07(6) . . ? N1 P2 Cl2 110.30(6) . . ? N2 P2 Cl2 107.75(7) . . ? Cl1 P2 Cl2 100.64(3) . . ? N3 P3 N2 119.06(8) . . ? N3 P3 Cl4 110.45(6) . . ? N2 P3 Cl4 108.40(6) . . ? N3 P3 Cl3 108.01(6) . . ? N2 P3 Cl3 108.62(7) . . ? Cl4 P3 Cl3 100.71(3) . . ? N7 P4 N5 117.72(8) . . ? N7 P4 N4 108.87(8) . . ? N5 P4 N4 110.68(8) . . ? N7 P4 Cl5 106.28(6) . . ? N5 P4 Cl5 107.48(7) . . ? N4 P4 Cl5 104.97(6) . . ? N5 P5 N6 118.64(8) . . ? N5 P5 Cl7 108.71(7) . . ? N6 P5 Cl7 109.18(6) . . ? N5 P5 Cl6 108.72(7) . . ? N6 P5 Cl6 108.79(6) . . ? Cl7 P5 Cl6 101.43(3) . . ? N7 P6 N6 118.13(8) . . ? N7 P6 Cl9 109.03(6) . . ? N6 P6 Cl9 108.48(6) . . ? N7 P6 Cl8 109.40(6) . . ? N6 P6 Cl8 108.68(7) . . ? Cl9 P6 Cl8 101.89(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.651 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.280 #===END