Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Aylin Uslu' _publ_contact_author_address ; Department of Chemistry Gebze Institute of Technology P.B. 141 Gebze Kocaeli 41400 TURKEY ; _publ_contact_author_email AYLIN@GYTE.EDU.TR _publ_section_title ; Stereogenic properties of spiranes combined with four equivalent conventional centres of chirality ; loop_ _publ_author_name 'Aylin Uslu' 'Simon Coles' 'David Davies' 'Robert J. Eaton' 'M. Hursthouse' 'Adem Kilic' ; R.A.Shaw ; data_2b _database_code_depnum_ccdc_archive 'CCDC 266980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H32 Cl4 N10 O4 P6' _chemical_formula_weight 720.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0203(8) _cell_length_b 9.6900(9) _cell_length_c 19.3728(17) _cell_angle_alpha 93.704(2) _cell_angle_beta 99.887(2) _cell_angle_gamma 111.292(2) _cell_volume 1539.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4404 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.42 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9434 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.68950 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 13034 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.37 _reflns_number_total 7354 _reflns_number_gt 5002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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^)+(0.0605P)^2^+1.4697P] 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 7354 _refine_ls_number_parameters 406 _refine_ls_number_restraints 204 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.004 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 P1 P 0.22646(10) 0.23013(9) 0.52560(4) 0.02558(18) Uani 1 1 d . . . N1 N 0.3155(4) 0.1969(3) 0.59591(15) 0.0327(6) Uani 1 1 d . . . P2 P 0.27337(11) 0.23260(10) 0.66929(4) 0.02719(19) Uani 1 1 d . . . N2 N 0.1222(4) 0.2773(3) 0.67018(14) 0.0325(6) Uani 1 1 d . . . P3 P 0.03451(11) 0.31647(10) 0.60035(4) 0.02757(19) Uani 1 1 d . . . N3 N 0.0752(3) 0.2752(3) 0.52803(14) 0.0307(6) Uani 1 1 d . . . P4 P 0.26239(13) 0.09298(11) 0.23158(5) 0.0371(2) Uani 1 1 d . . . N4 N 0.3957(5) 0.2167(4) 0.20220(18) 0.0540(10) Uani 1 1 d . A . P5 P 0.4581(2) 0.18150(15) 0.13455(6) 0.0621(4) Uani 1 1 d DU . . N5 N 0.3865(6) 0.0161(5) 0.0965(2) 0.0747(13) Uani 1 1 d . A . P6 P 0.23024(18) -0.10273(15) 0.11653(6) 0.0600(3) Uani 1 1 d DU . . N6 N 0.1768(4) -0.0661(4) 0.18719(17) 0.0495(9) Uani 1 1 d . A . O1 O 0.1741(3) 0.0904(2) 0.46746(12) 0.0299(5) Uani 1 1 d . . . O2 O 0.3581(3) 0.3558(2) 0.49526(11) 0.0284(5) Uani 1 1 d . . . O3 O 0.1254(3) 0.1499(3) 0.24505(12) 0.0417(6) Uani 1 1 d . . . O4 O 0.3394(3) 0.0744(3) 0.30817(12) 0.0347(5) Uani 1 1 d . . . C1 C 0.1147(4) 0.1120(4) 0.39615(17) 0.0300(7) Uani 1 1 d . . . H1A H 0.0156 0.1344 0.3948 0.036 Uiso 1 1 calc R . . H1B H 0.0850 0.0187 0.3636 0.036 Uiso 1 1 calc R . . C2 C 0.3013(4) 0.3827(4) 0.42454(16) 0.0289(7) Uani 1 1 d . . . H2A H 0.3906 0.4627 0.4101 0.035 Uiso 1 1 calc R . . H2B H 0.2105 0.4171 0.4247 0.035 Uiso 1 1 calc R . . C3 C 0.1689(5) 0.2736(4) 0.30065(17) 0.0335(8) Uani 1 1 d . . . H3A H 0.0705 0.2932 0.3054 0.040 Uiso 1 1 calc R . . H3B H 0.2477 0.3646 0.2878 0.040 Uiso 1 1 calc R . . C4 C 0.3898(4) 0.2011(4) 0.36340(17) 0.0319(7) Uani 1 1 d . . . H4A H 0.4752 0.2882 0.3511 0.038 Uiso 1 1 calc R . . H4B H 0.4359 0.1759 0.4087 0.038 Uiso 1 1 calc R . . C5 C 0.2436(4) 0.2404(3) 0.37143(16) 0.0259(6) Uani 1 1 d . . . Cl1 Cl 0.47286(12) 0.41056(11) 0.72545(5) 0.0465(2) Uani 1 1 d . . . Cl2 Cl 0.10327(12) 0.54687(10) 0.61484(5) 0.0426(2) Uani 1 1 d . . . N7 N 0.2608(3) 0.0949(3) 0.71521(15) 0.0323(6) Uani 1 1 d . . . C6 C 0.3735(5) 0.0199(5) 0.7104(2) 0.0435(9) Uani 1 1 d . . . H6A H 0.3880 0.0107 0.6616 0.065 Uiso 1 1 calc R . . H6B H 0.3293 -0.0799 0.7245 0.065 Uiso 1 1 calc R . . H6C H 0.4787 0.0785 0.7418 0.065 Uiso 1 1 calc R . . C7 C 0.2311(5) 0.1150(5) 0.7869(2) 0.0448(9) Uani 1 1 d . . . H7A H 0.1554 0.1665 0.7864 0.067 Uiso 1 1 calc R . . H7B H 0.3342 0.1749 0.8196 0.067 Uiso 1 1 calc R . . H7C H 0.1840 0.0171 0.8024 0.067 Uiso 1 1 calc R . . N8 N -0.1614(3) 0.2493(3) 0.59533(16) 0.0333(6) Uani 1 1 d . . . C8 C -0.2213(5) 0.2790(5) 0.6574(2) 0.0427(9) Uani 1 1 d . . . H8A H -0.1385 0.2928 0.7001 0.064 Uiso 1 1 calc R . . H8B H -0.3209 0.1944 0.6592 0.064 Uiso 1 1 calc R . . H8C H -0.2447 0.3699 0.6548 0.064 Uiso 1 1 calc R . . C9 C -0.2730(5) 0.2257(5) 0.5279(2) 0.0442(9) Uani 1 1 d . . . H9A H -0.2226 0.2063 0.4894 0.066 Uiso 1 1 calc R . . H9B H -0.2981 0.3151 0.5222 0.066 Uiso 1 1 calc R . . H9C H -0.3737 0.1397 0.5268 0.066 Uiso 1 1 calc R . . Cl3 Cl 0.4433(6) 0.3336(4) 0.07027(19) 0.0667(10) Uani 0.50 1 d PDU A 1 Cl4 Cl 0.2826(6) -0.2803(4) 0.1229(3) 0.0518(10) Uani 0.50 1 d PDU A 1 N9 N 0.6626(18) 0.249(2) 0.1445(9) 0.092(5) Uani 0.50 1 d PDU A 1 C10 C 0.7654(13) 0.3864(11) 0.1973(5) 0.064(2) Uani 0.50 1 d PDU A 1 H10A H 0.6986 0.4076 0.2281 0.096 Uiso 0.50 1 calc PR A 1 H10B H 0.8088 0.4719 0.1722 0.096 Uiso 0.50 1 calc PR A 1 H10C H 0.8557 0.3686 0.2261 0.096 Uiso 0.50 1 calc PR A 1 C11 C 0.7540(15) 0.2002(12) 0.1017(5) 0.071(3) Uani 0.50 1 d PDU A 1 H11A H 0.6826 0.1060 0.0718 0.106 Uiso 0.50 1 calc PR A 1 H11B H 0.8434 0.1847 0.1324 0.106 Uiso 0.50 1 calc PR A 1 H11C H 0.7985 0.2763 0.0718 0.106 Uiso 0.50 1 calc PR A 1 N10 N 0.0740(17) -0.146(2) 0.0437(7) 0.089(6) Uani 0.50 1 d PDU A 1 C12 C -0.0786(16) -0.243(3) 0.0578(9) 0.186(11) Uani 0.50 1 d PDU A 1 H12A H -0.0830 -0.2163 0.1069 0.279 Uiso 0.50 1 calc PR A 1 H12B H -0.0887 -0.3469 0.0503 0.279 Uiso 0.50 1 calc PR A 1 H12C H -0.1683 -0.2302 0.0258 0.279 Uiso 0.50 1 calc PR A 1 C13 C 0.1068(19) -0.1548(17) -0.0264(5) 0.112(5) Uani 0.50 1 d PDU A 1 H13A H 0.2114 -0.0756 -0.0272 0.168 Uiso 0.50 1 calc PR A 1 H13B H 0.0202 -0.1419 -0.0603 0.168 Uiso 0.50 1 calc PR A 1 H13C H 0.1110 -0.2525 -0.0395 0.168 Uiso 0.50 1 calc PR A 1 Cl5 Cl 0.6896(6) 0.2465(6) 0.1627(3) 0.0725(11) Uani 0.50 1 d PDU A 2 Cl6 Cl 0.0307(8) -0.1696(7) 0.0408(3) 0.100(2) Uani 0.50 1 d PDU A 2 N11 N 0.403(2) 0.2658(13) 0.0647(7) 0.080(4) Uani 0.50 1 d PDU A 2 C14 C 0.473(3) 0.2511(19) 0.0030(7) 0.142(7) Uani 0.50 1 d PDU A 2 H14A H 0.4657 0.1481 -0.0067 0.213 Uiso 0.50 1 calc PR A 2 H14B H 0.5870 0.3198 0.0124 0.213 Uiso 0.50 1 calc PR A 2 H14C H 0.4119 0.2755 -0.0382 0.213 Uiso 0.50 1 calc PR A 2 C15 C 0.403(3) 0.4045(17) 0.0872(5) 0.147(8) Uani 0.50 1 d PDU A 2 H15A H 0.3484 0.3971 0.1271 0.221 Uiso 0.50 1 calc PR A 2 H15B H 0.3455 0.4377 0.0483 0.221 Uiso 0.50 1 calc PR A 2 H15C H 0.5156 0.4768 0.1021 0.221 Uiso 0.50 1 calc PR A 2 N12 N 0.257(2) -0.2692(18) 0.1211(12) 0.071(5) Uani 0.50 1 d PDU A 2 C16 C 0.1392(18) -0.3922(15) 0.1482(7) 0.102(4) Uani 0.50 1 d PDU A 2 H16A H 0.0775 -0.3521 0.1750 0.153 Uiso 0.50 1 calc PR A 2 H16B H 0.1976 -0.4403 0.1792 0.153 Uiso 0.50 1 calc PR A 2 H16C H 0.0643 -0.4659 0.1084 0.153 Uiso 0.50 1 calc PR A 2 C17 C 0.3498(17) -0.3151(14) 0.0769(6) 0.090(4) Uani 0.50 1 d PDU A 2 H17A H 0.4212 -0.2275 0.0597 0.136 Uiso 0.50 1 calc PR A 2 H17B H 0.2751 -0.3874 0.0366 0.136 Uiso 0.50 1 calc PR A 2 H17C H 0.4158 -0.3615 0.1046 0.136 Uiso 0.50 1 calc PR A 2 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 0.0262(4) 0.0282(4) 0.0261(4) 0.0056(3) 0.0098(3) 0.0126(3) N1 0.0336(16) 0.0442(17) 0.0303(14) 0.0098(12) 0.0115(12) 0.0234(14) P2 0.0272(4) 0.0308(4) 0.0268(4) 0.0072(3) 0.0094(3) 0.0126(4) N2 0.0388(17) 0.0408(16) 0.0294(14) 0.0089(12) 0.0163(12) 0.0235(14) P3 0.0290(5) 0.0288(4) 0.0319(4) 0.0085(3) 0.0128(3) 0.0155(4) N3 0.0293(15) 0.0389(16) 0.0303(14) 0.0063(12) 0.0087(12) 0.0191(13) P4 0.0482(6) 0.0406(5) 0.0275(4) -0.0003(4) 0.0094(4) 0.0228(5) N4 0.080(3) 0.046(2) 0.0440(19) 0.0052(16) 0.0331(19) 0.0242(19) P5 0.1073(11) 0.0579(7) 0.0394(6) 0.0160(5) 0.0378(7) 0.0410(8) N5 0.108(4) 0.073(3) 0.050(2) 0.001(2) 0.040(2) 0.033(3) P6 0.0763(9) 0.0653(8) 0.0366(6) -0.0155(5) 0.0063(6) 0.0310(7) N6 0.057(2) 0.048(2) 0.0397(18) -0.0112(15) 0.0103(16) 0.0185(18) O1 0.0354(13) 0.0256(11) 0.0311(12) 0.0061(9) 0.0122(10) 0.0118(10) O2 0.0294(12) 0.0278(12) 0.0240(11) 0.0033(9) 0.0071(9) 0.0057(10) O3 0.0472(16) 0.0521(16) 0.0294(12) -0.0067(11) 0.0006(11) 0.0286(13) O4 0.0427(15) 0.0402(14) 0.0290(12) 0.0009(10) 0.0102(10) 0.0242(12) C1 0.0286(18) 0.0294(17) 0.0300(16) 0.0002(13) 0.0061(13) 0.0097(14) C2 0.0323(18) 0.0295(17) 0.0258(15) 0.0052(13) 0.0099(13) 0.0109(14) C3 0.042(2) 0.0373(19) 0.0261(16) 0.0004(14) 0.0060(14) 0.0218(16) C4 0.0305(18) 0.0406(19) 0.0272(16) 0.0016(14) 0.0077(13) 0.0165(16) C5 0.0267(17) 0.0262(16) 0.0265(15) 0.0011(12) 0.0065(12) 0.0121(13) Cl1 0.0396(5) 0.0417(5) 0.0468(5) 0.0011(4) 0.0105(4) 0.0024(4) Cl2 0.0431(5) 0.0299(4) 0.0605(6) 0.0096(4) 0.0175(4) 0.0168(4) N7 0.0275(15) 0.0396(16) 0.0328(15) 0.0130(12) 0.0079(12) 0.0143(13) C6 0.047(2) 0.046(2) 0.048(2) 0.0186(18) 0.0144(18) 0.0264(19) C7 0.041(2) 0.064(3) 0.037(2) 0.0214(19) 0.0157(17) 0.024(2) N8 0.0279(16) 0.0363(16) 0.0416(16) 0.0110(13) 0.0146(12) 0.0148(13) C8 0.042(2) 0.045(2) 0.054(2) 0.0172(18) 0.0264(18) 0.0212(18) C9 0.033(2) 0.047(2) 0.053(2) 0.0038(18) 0.0057(17) 0.0181(18) Cl3 0.103(3) 0.074(3) 0.0413(14) 0.0261(17) 0.0189(14) 0.051(2) Cl4 0.0564(18) 0.0446(15) 0.058(2) -0.0102(14) 0.0097(15) 0.0269(15) N9 0.095(7) 0.128(11) 0.074(10) 0.045(7) 0.048(6) 0.048(7) C10 0.080(6) 0.066(6) 0.060(6) 0.011(4) 0.029(5) 0.037(5) C11 0.105(8) 0.079(7) 0.050(5) 0.020(5) 0.045(6) 0.046(7) N10 0.079(7) 0.190(17) 0.047(6) 0.001(8) 0.026(5) 0.104(9) C12 0.040(6) 0.33(3) 0.140(14) -0.091(14) 0.016(7) 0.037(11) C13 0.187(14) 0.138(12) 0.027(4) -0.004(6) 0.001(6) 0.093(11) Cl5 0.087(2) 0.092(3) 0.060(2) 0.0358(18) 0.0388(17) 0.043(2) Cl6 0.140(5) 0.102(3) 0.056(2) -0.010(2) -0.018(3) 0.067(3) N11 0.140(11) 0.075(9) 0.050(6) 0.024(6) 0.043(6) 0.058(9) C14 0.28(2) 0.144(14) 0.062(7) 0.038(8) 0.089(11) 0.120(15) C15 0.34(2) 0.159(13) 0.035(6) 0.027(7) 0.035(9) 0.201(17) N12 0.095(11) 0.083(8) 0.064(8) 0.012(6) 0.010(6) 0.069(7) C16 0.148(13) 0.078(7) 0.074(8) 0.001(6) 0.020(7) 0.039(8) C17 0.127(11) 0.093(9) 0.070(7) -0.001(6) 0.012(7) 0.069(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.573(3) . ? P1 O1 1.575(2) . ? P1 N3 1.583(3) . ? P1 O2 1.588(2) . ? N1 P2 1.582(3) . ? P2 N2 1.576(3) . ? P2 N7 1.632(3) . ? P2 Cl1 2.0559(13) . ? N2 P3 1.587(3) . ? P3 N3 1.571(3) . ? P3 N8 1.629(3) . ? P3 Cl2 2.0740(12) . ? P4 N6 1.565(3) . ? P4 N4 1.576(4) . ? P4 O3 1.577(3) . ? P4 O4 1.577(2) . ? N4 P5 1.577(3) . ? P5 N5 1.569(5) . ? P5 N9 1.689(15) . ? P5 N11 1.717(12) . ? P5 Cl5 1.915(5) . ? P5 Cl3 2.016(3) . ? N5 P6 1.590(5) . ? P6 N6 1.587(3) . ? P6 N12 1.722(14) . ? P6 N10 1.722(14) . ? P6 Cl4 1.949(5) . ? P6 Cl6 1.983(6) . ? O1 C1 1.451(4) . ? O2 C2 1.453(4) . ? O3 C3 1.448(4) . ? O4 C4 1.455(4) . ? C1 C5 1.532(5) . ? C2 C5 1.530(4) . ? C3 C5 1.528(4) . ? C4 C5 1.528(5) . ? N7 C6 1.460(5) . ? N7 C7 1.473(5) . ? N8 C9 1.454(5) . ? N8 C8 1.453(5) . ? N9 C11 1.435(13) . ? N9 C10 1.510(13) . ? N10 C12 1.438(14) . ? N10 C13 1.442(12) . ? N11 C15 1.386(11) . ? N11 C14 1.465(12) . ? N12 C17 1.447(13) . ? N12 C16 1.476(13) . ? 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 N1 P1 O1 108.28(14) . . ? N1 P1 N3 118.40(15) . . ? O1 P1 N3 109.20(15) . . ? N1 P1 O2 107.98(15) . . ? O1 P1 O2 102.37(12) . . ? N3 P1 O2 109.42(14) . . ? P1 N1 P2 120.60(18) . . ? N2 P2 N1 119.23(15) . . ? N2 P2 N7 109.68(15) . . ? N1 P2 N7 109.57(16) . . ? N2 P2 Cl1 106.12(12) . . ? N1 P2 Cl1 106.43(13) . . ? N7 P2 Cl1 104.74(12) . . ? P2 N2 P3 120.14(17) . . ? N3 P3 N2 118.32(15) . . ? N3 P3 N8 110.65(16) . . ? N2 P3 N8 109.46(15) . . ? N3 P3 Cl2 106.49(12) . . ? N2 P3 Cl2 105.92(12) . . ? N8 P3 Cl2 105.03(12) . . ? P3 N3 P1 121.18(18) . . ? N6 P4 N4 118.21(19) . . ? N6 P4 O3 107.70(18) . . ? N4 P4 O3 110.00(18) . . ? N6 P4 O4 107.90(17) . . ? N4 P4 O4 108.99(18) . . ? O3 P4 O4 102.95(13) . . ? P4 N4 P5 122.4(2) . . ? N5 P5 N4 118.2(2) . . ? N5 P5 N9 108.7(6) . . ? N4 P5 N9 114.7(5) . . ? N5 P5 N11 98.6(5) . . ? N4 P5 N11 112.7(5) . . ? N9 P5 N11 101.5(9) . . ? N5 P5 Cl5 109.2(3) . . ? N4 P5 Cl5 106.5(2) . . ? N9 P5 Cl5 10.6(8) . . ? N11 P5 Cl5 111.6(6) . . ? N5 P5 Cl3 114.4(2) . . ? N4 P5 Cl3 106.9(2) . . ? N9 P5 Cl3 90.7(7) . . ? N11 P5 Cl3 16.6(5) . . ? Cl5 P5 Cl3 99.9(2) . . ? P5 N5 P6 119.5(3) . . ? N6 P6 N5 119.4(2) . . ? N6 P6 N12 106.8(6) . . ? N5 P6 N12 108.7(6) . . ? N6 P6 N10 111.7(4) . . ? N5 P6 N10 106.5(6) . . ? N12 P6 N10 102.4(11) . . ? N6 P6 Cl4 108.5(2) . . ? N5 P6 Cl4 103.6(2) . . ? N12 P6 Cl4 5.4(8) . . ? N10 P6 Cl4 106.1(7) . . ? N6 P6 Cl6 105.8(2) . . ? N5 P6 Cl6 114.4(3) . . ? N12 P6 Cl6 99.8(8) . . ? N10 P6 Cl6 7.9(6) . . ? Cl4 P6 Cl6 104.0(3) . . ? P4 N6 P6 120.4(2) . . ? C1 O1 P1 115.3(2) . . ? C2 O2 P1 115.0(2) . . ? C3 O3 P4 117.9(2) . . ? C4 O4 P4 117.3(2) . . ? O1 C1 C5 111.1(3) . . ? O2 C2 C5 110.8(3) . . ? O3 C3 C5 111.4(3) . . ? O4 C4 C5 109.8(3) . . ? C3 C5 C1 109.4(3) . . ? C3 C5 C2 107.4(3) . . ? C1 C5 C2 110.2(3) . . ? C3 C5 C4 109.6(3) . . ? C1 C5 C4 111.0(3) . . ? C2 C5 C4 109.2(3) . . ? C6 N7 C7 113.8(3) . . ? C6 N7 P2 117.8(2) . . ? C7 N7 P2 116.2(3) . . ? C9 N8 C8 115.3(3) . . ? C9 N8 P3 120.5(2) . . ? C8 N8 P3 118.1(3) . . ? C11 N9 C10 113.5(11) . . ? C11 N9 P5 126.7(11) . . ? C10 N9 P5 119.5(10) . . ? C12 N10 C13 120.7(14) . . ? C12 N10 P6 111.7(11) . . ? C13 N10 P6 119.9(9) . . ? C15 N11 C14 118.1(11) . . ? C15 N11 P5 111.8(9) . . ? C14 N11 P5 115.3(10) . . ? C17 N12 C16 114.9(12) . . ? C17 N12 P6 121.7(11) . . ? C16 N12 P6 119.4(11) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.802 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.083 # Attachment '2c.CIF' data_3c _database_code_depnum_ccdc_archive 'CCDC 266981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H32 Cl4 N10 O4 P6' _chemical_formula_weight 720.11 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 10.376(5) _cell_length_b 15.323(8) _cell_length_c 20.706(10) _cell_angle_alpha 108.439(9) _cell_angle_beta 97.965(10) _cell_angle_gamma 90.189(9) _cell_volume 3089(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5669 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.62 _exptl_crystal_description plate _exptl_crystal_colour colurless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6903 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 10 _diffrn_reflns_number 24592 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.1752 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.56 _reflns_number_total 12490 _reflns_number_gt 7500 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _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^)+(0.1212P)^2^+0.0000P] 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 0.0045(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 12490 _refine_ls_number_parameters 684 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1450 _refine_ls_R_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.2697 _refine_ls_wR_factor_gt 0.2287 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.131 _refine_ls_shift/su_mean 0.004 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 -0.6392(8) 0.3168(5) -0.2181(4) 0.0252(16) Uani 1 1 d . . . H1A H -0.5789 0.3311 -0.2462 0.038 Uiso 1 1 calc R . . H1B H -0.6155 0.3558 -0.1701 0.038 Uiso 1 1 calc R . . H1C H -0.7283 0.3284 -0.2352 0.038 Uiso 1 1 calc R . . C2 C -0.6683(8) 0.1568(5) -0.2942(4) 0.0265(17) Uani 1 1 d . . . H2A H -0.7577 0.1674 -0.3115 0.040 Uiso 1 1 calc R . . H2B H -0.6628 0.0926 -0.2950 0.040 Uiso 1 1 calc R . . H2C H -0.6086 0.1693 -0.3233 0.040 Uiso 1 1 calc R . . C3 C -0.3538(9) -0.0720(5) -0.1910(4) 0.034(2) Uani 1 1 d . . . H3A H -0.2650 -0.0853 -0.2009 0.052 Uiso 1 1 calc R . . H3B H -0.4023 -0.0519 -0.2275 0.052 Uiso 1 1 calc R . . H3C H -0.3975 -0.1277 -0.1890 0.052 Uiso 1 1 calc R . . C4 C -0.2675(9) -0.0192(6) -0.0663(5) 0.040(2) Uani 1 1 d . . . H4A H -0.3038 -0.0752 -0.0608 0.060 Uiso 1 1 calc R . . H4B H -0.2668 0.0322 -0.0236 0.060 Uiso 1 1 calc R . . H4C H -0.1783 -0.0289 -0.0766 0.060 Uiso 1 1 calc R . . C5 C -0.2800(7) 0.2828(5) 0.0761(3) 0.0225(15) Uani 1 1 d . . . H5A H -0.1920 0.3119 0.0965 0.027 Uiso 1 1 calc R . . H5B H -0.2774 0.2169 0.0725 0.027 Uiso 1 1 calc R . . C6 C -0.3778(7) 0.3286(5) 0.1236(4) 0.0198(15) Uani 1 1 d . . . C7 C -0.5185(6) 0.2915(5) 0.0905(3) 0.0173(14) Uani 1 1 d . . . H7A H -0.5297 0.2266 0.0888 0.021 Uiso 1 1 calc R . . H7B H -0.5812 0.3280 0.1188 0.021 Uiso 1 1 calc R . . C8 C -0.3426(7) 0.3052(5) 0.1899(4) 0.0221(15) Uani 1 1 d . . . H8A H -0.3612 0.2385 0.1799 0.027 Uiso 1 1 calc R . . H8B H -0.2478 0.3178 0.2054 0.027 Uiso 1 1 calc R . . C9 C -0.3669(7) 0.4329(5) 0.1387(4) 0.0247(16) Uani 1 1 d . . . H9A H -0.2743 0.4548 0.1533 0.030 Uiso 1 1 calc R . . H9B H -0.3986 0.4478 0.0963 0.030 Uiso 1 1 calc R . . C10 C -0.0204(9) 0.6252(7) 0.3085(5) 0.040(2) Uani 1 1 d . . . H10A H 0.0119 0.6769 0.2959 0.061 Uiso 1 1 calc R . . H10B H -0.0615 0.5772 0.2669 0.061 Uiso 1 1 calc R . . H10C H 0.0525 0.6000 0.3312 0.061 Uiso 1 1 calc R . . C11 C -0.0645(11) 0.7333(7) 0.4169(6) 0.064(3) Uani 1 1 d . . . H11A H 0.0247 0.7203 0.4328 0.096 Uiso 1 1 calc R . . H11B H -0.1179 0.7400 0.4535 0.096 Uiso 1 1 calc R . . H11C H -0.0632 0.7905 0.4053 0.096 Uiso 1 1 calc R . . C12 C -0.5110(11) 0.6371(7) 0.5139(4) 0.048(3) Uani 1 1 d . . . H12A H -0.5658 0.6897 0.5161 0.072 Uiso 1 1 calc R . . H12B H -0.4190 0.6584 0.5236 0.072 Uiso 1 1 calc R . . H12C H -0.5301 0.6090 0.5482 0.072 Uiso 1 1 calc R . . C13 C -0.6710(9) 0.5295(6) 0.4297(5) 0.041(2) Uani 1 1 d . . . H13A H -0.6898 0.5092 0.4679 0.062 Uiso 1 1 calc R . . H13B H -0.6814 0.4768 0.3872 0.062 Uiso 1 1 calc R . . H13C H -0.7315 0.5765 0.4241 0.062 Uiso 1 1 calc R . . C14 C -0.3919(13) 0.0133(10) -0.4111(6) 0.086(5) Uani 1 1 d . . . H14A H -0.4215 0.0417 -0.4464 0.129 Uiso 1 1 calc R . . H14B H -0.3574 0.0614 -0.3680 0.129 Uiso 1 1 calc R . . H14C H -0.4654 -0.0209 -0.4036 0.129 Uiso 1 1 calc R . . C15 C -0.3295(11) -0.1190(7) -0.5006(5) 0.059(3) Uani 1 1 d . . . H15A H -0.4072 -0.1542 -0.4989 0.088 Uiso 1 1 calc R . . H15B H -0.2587 -0.1607 -0.5123 0.088 Uiso 1 1 calc R . . H15C H -0.3493 -0.0885 -0.5356 0.088 Uiso 1 1 calc R . . C16 C 0.1632(11) -0.2470(7) -0.4180(5) 0.054(3) Uani 1 1 d . . . H16A H 0.2001 -0.2339 -0.4552 0.080 Uiso 1 1 calc R . . H16B H 0.0719 -0.2690 -0.4339 0.080 Uiso 1 1 calc R . . H16C H 0.2125 -0.2944 -0.4044 0.080 Uiso 1 1 calc R . . C17 C 0.3022(9) -0.1324(7) -0.3212(5) 0.049(2) Uani 1 1 d . . . H17A H 0.3381 -0.1805 -0.3031 0.073 Uiso 1 1 calc R . . H17B H 0.2987 -0.0754 -0.2830 0.073 Uiso 1 1 calc R . . H17C H 0.3579 -0.1214 -0.3527 0.073 Uiso 1 1 calc R . . C18 C 0.0661(7) 0.0691(5) -0.1337(4) 0.0266(17) Uani 1 1 d . . . H18A H 0.1506 0.0489 -0.1490 0.032 Uiso 1 1 calc R . . H18B H 0.0600 0.0540 -0.0911 0.032 Uiso 1 1 calc R . . C19 C 0.0575(8) 0.1726(5) -0.1198(4) 0.0240(16) Uani 1 1 d . . . C20 C 0.0567(7) 0.1962(4) -0.1855(4) 0.0233(16) Uani 1 1 d . . . H20A H 0.0440 0.2629 -0.1756 0.028 Uiso 1 1 calc R . . H20B H 0.1428 0.1838 -0.2010 0.028 Uiso 1 1 calc R . . C21 C 0.1825(7) 0.2189(5) -0.0723(4) 0.0261(17) Uani 1 1 d . . . H21A H 0.2592 0.1902 -0.0926 0.031 Uiso 1 1 calc R . . H21B H 0.1873 0.2850 -0.0683 0.031 Uiso 1 1 calc R . . C22 C -0.0624(7) 0.2097(5) -0.0866(4) 0.0228(16) Uani 1 1 d . . . H22A H -0.0707 0.2749 -0.0845 0.027 Uiso 1 1 calc R . . H22B H -0.1413 0.1742 -0.1155 0.027 Uiso 1 1 calc R . . C23 C -0.0193(8) 0.1831(5) 0.2189(4) 0.0254(16) Uani 1 1 d . . . H23A H 0.0522 0.1706 0.2505 0.038 Uiso 1 1 calc R . . H23B H -0.0127 0.1452 0.1717 0.038 Uiso 1 1 calc R . . H23C H -0.1028 0.1683 0.2311 0.038 Uiso 1 1 calc R . . C24 C -0.0068(8) 0.3425(5) 0.2954(4) 0.0250(16) Uani 1 1 d . . . H24A H -0.0903 0.3372 0.3112 0.037 Uiso 1 1 calc R . . H24B H 0.0097 0.4061 0.2967 0.037 Uiso 1 1 calc R . . H24C H 0.0632 0.3256 0.3254 0.037 Uiso 1 1 calc R . . C25 C 0.2695(9) 0.5249(6) 0.0725(4) 0.037(2) Uani 1 1 d . . . H25A H 0.2204 0.5755 0.0638 0.056 Uiso 1 1 calc R . . H25B H 0.2580 0.4712 0.0306 0.056 Uiso 1 1 calc R . . H25C H 0.3621 0.5441 0.0857 0.056 Uiso 1 1 calc R . . C26 C 0.2498(8) 0.5731(5) 0.1961(4) 0.034(2) Uani 1 1 d . . . H26A H 0.3440 0.5867 0.2081 0.050 Uiso 1 1 calc R . . H26B H 0.2179 0.5515 0.2310 0.050 Uiso 1 1 calc R . . H26C H 0.2061 0.6290 0.1940 0.050 Uiso 1 1 calc R . . N1 N -0.5383(6) 0.0881(4) -0.1755(3) 0.0235(13) Uani 1 1 d . . . N2 N -0.4540(6) 0.1382(4) -0.0369(3) 0.0264(14) Uani 1 1 d . . . N3 N -0.4835(6) 0.2695(4) -0.1008(3) 0.0197(12) Uani 1 1 d U . . N4 N -0.6318(6) 0.2192(4) -0.2223(3) 0.0183(12) Uani 1 1 d . . . N5 N -0.3488(6) 0.0024(4) -0.1236(3) 0.0252(14) Uani 1 1 d . . . N6 N -0.2564(6) 0.5011(4) 0.2944(3) 0.0247(14) Uani 1 1 d . . . N7 N -0.3315(7) 0.6285(5) 0.4065(3) 0.0335(16) Uani 1 1 d . . . N8 N -0.5103(6) 0.5054(4) 0.3118(3) 0.0278(15) Uani 1 1 d . . . N9 N -0.1188(7) 0.6582(5) 0.3568(3) 0.0344(16) Uani 1 1 d . . . N10 N -0.5383(7) 0.5681(5) 0.4442(3) 0.0342(16) Uani 1 1 d . . . N11 N -0.0682(7) -0.1280(5) -0.4024(4) 0.0390(18) Uani 1 1 d . . . N12 N 0.0799(7) -0.0011(5) -0.2930(4) 0.0343(16) Uani 1 1 d . . . N13 N -0.1825(7) -0.0023(4) -0.3042(3) 0.0318(16) Uani 1 1 d . . . N14 N -0.2896(7) -0.0499(5) -0.4337(4) 0.0356(17) Uani 1 1 d . . . N15 N 0.1707(7) -0.1620(5) -0.3582(4) 0.0348(16) Uani 1 1 d . . . N16 N 0.0761(6) 0.2318(4) 0.1043(3) 0.0207(13) Uani 1 1 d . . . N17 N 0.0569(6) 0.4131(4) 0.1776(3) 0.0232(13) Uani 1 1 d . . . N18 N 0.0698(7) 0.3629(4) 0.0401(3) 0.0270(15) Uani 1 1 d . . . N19 N -0.0114(6) 0.2803(4) 0.2243(3) 0.0202(13) Uani 1 1 d . . . N20 N 0.2215(6) 0.5006(4) 0.1281(3) 0.0230(13) Uani 1 1 d . . . O1 O -0.3133(4) 0.2907(3) 0.0072(2) 0.0214(11) Uani 1 1 d . . . O2 O -0.5450(4) 0.2975(3) 0.0202(2) 0.0190(10) Uani 1 1 d . . . O3 O -0.4121(5) 0.3562(3) 0.2459(3) 0.0229(11) Uani 1 1 d . . . O4 O -0.4420(5) 0.4801(3) 0.1922(3) 0.0244(11) Uani 1 1 d . . . O5 O -0.0407(5) 0.0224(3) -0.1870(3) 0.0285(12) Uani 1 1 d . . . O6 O -0.0433(5) 0.1454(3) -0.2410(3) 0.0274(12) Uani 1 1 d . . . O7 O 0.1863(5) 0.2100(3) -0.0036(2) 0.0226(11) Uani 1 1 d . . . O8 O -0.0540(4) 0.2032(3) -0.0167(2) 0.0194(10) Uani 1 1 d . . . P1 P -0.51182(17) 0.19088(11) -0.17389(9) 0.0166(4) Uani 1 1 d . . . P2 P -0.47881(18) 0.05975(11) -0.10963(9) 0.0187(4) Uani 1 1 d . . . P3 P -0.45183(17) 0.24413(11) -0.03197(9) 0.0169(4) Uani 1 1 d . . . P4 P -0.40284(19) 0.46510(12) 0.26544(10) 0.0223(4) Uani 1 1 d . . . P5 P -0.2176(2) 0.58048(13) 0.36609(10) 0.0269(5) Uani 1 1 d . . . P6 P -0.4765(2) 0.59053(13) 0.38150(10) 0.0272(5) Uani 1 1 d . . . P7 P -0.1960(2) -0.08315(14) -0.37461(11) 0.0301(5) Uani 1 1 d . . . P8 P 0.0705(2) -0.08195(14) -0.36584(11) 0.0301(5) Uani 1 1 d . . . P9 P -0.0463(2) 0.03684(13) -0.26089(10) 0.0256(5) Uani 1 1 d . . . P10 P 0.07001(17) 0.25695(11) 0.03521(9) 0.0172(4) Uani 1 1 d . . . P11 P 0.08524(17) 0.31082(11) 0.17704(9) 0.0164(4) Uani 1 1 d . . . P12 P 0.08286(19) 0.44100(11) 0.11234(10) 0.0198(4) Uani 1 1 d . . . Cl1 Cl -0.61451(19) -0.03317(12) -0.10291(10) 0.0297(4) Uani 1 1 d . . . Cl2 Cl -0.35293(18) 0.19076(13) -0.22294(10) 0.0272(4) Uani 1 1 d . . . Cl3 Cl -0.1063(2) 0.52421(17) 0.43316(11) 0.0462(6) Uani 1 1 d . . . Cl4 Cl -0.5812(2) 0.69860(13) 0.36691(11) 0.0358(5) Uani 1 1 d . . . Cl5 Cl -0.2988(2) -0.18847(15) -0.36066(12) 0.0455(6) Uani 1 1 d . . . Cl6 Cl 0.1433(3) -0.02862(17) -0.43418(12) 0.0487(6) Uani 1 1 d . . . Cl7 Cl 0.27048(17) 0.31436(13) 0.22855(10) 0.0271(4) Uani 1 1 d . . . Cl8 Cl -0.05892(19) 0.53202(12) 0.10278(10) 0.0291(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 0.028(4) 0.014(3) 0.032(4) 0.007(3) 0.000(3) 0.007(3) C2 0.030(4) 0.024(4) 0.019(4) 0.000(3) -0.001(3) 0.005(3) C3 0.041(5) 0.017(4) 0.033(5) -0.011(3) 0.009(4) 0.007(3) C4 0.037(5) 0.037(5) 0.047(5) 0.013(4) 0.006(4) 0.020(4) C5 0.020(4) 0.023(4) 0.015(4) -0.004(3) -0.005(3) 0.003(3) C6 0.022(4) 0.010(3) 0.019(4) -0.004(3) -0.001(3) 0.002(3) C7 0.014(3) 0.015(3) 0.016(3) -0.002(3) -0.002(3) 0.002(3) C8 0.026(4) 0.009(3) 0.026(4) -0.001(3) 0.004(3) 0.001(3) C9 0.028(4) 0.009(3) 0.030(4) -0.002(3) -0.001(3) -0.003(3) C10 0.033(5) 0.042(5) 0.037(5) 0.001(4) 0.002(4) 0.000(4) C11 0.063(7) 0.039(6) 0.060(7) -0.024(5) 0.004(6) -0.014(5) C12 0.082(8) 0.041(5) 0.016(4) -0.001(4) 0.010(4) 0.016(5) C13 0.042(5) 0.038(5) 0.049(6) 0.018(4) 0.014(4) 0.008(4) C14 0.090(10) 0.081(9) 0.062(8) -0.001(7) -0.018(7) 0.043(8) C15 0.068(7) 0.048(6) 0.035(5) -0.008(5) -0.024(5) 0.015(5) C16 0.078(8) 0.037(5) 0.041(6) 0.004(4) 0.012(5) 0.036(5) C17 0.045(6) 0.056(6) 0.046(6) 0.019(5) 0.003(5) 0.010(5) C18 0.024(4) 0.013(4) 0.033(4) -0.004(3) 0.000(3) 0.004(3) C19 0.037(4) 0.011(3) 0.018(4) -0.004(3) 0.006(3) 0.003(3) C20 0.030(4) 0.004(3) 0.027(4) -0.005(3) -0.003(3) 0.000(3) C21 0.022(4) 0.026(4) 0.029(4) 0.003(3) 0.012(3) 0.003(3) C22 0.023(4) 0.019(4) 0.019(4) -0.003(3) -0.003(3) 0.004(3) C23 0.035(4) 0.010(3) 0.031(4) 0.006(3) 0.006(3) 0.001(3) C24 0.031(4) 0.018(4) 0.022(4) 0.000(3) 0.007(3) 0.007(3) C25 0.043(5) 0.030(5) 0.038(5) 0.009(4) 0.010(4) -0.005(4) C26 0.024(4) 0.013(4) 0.044(5) -0.011(3) -0.011(4) -0.006(3) N1 0.035(4) 0.007(3) 0.023(3) -0.001(2) -0.002(3) -0.002(2) N2 0.040(4) 0.007(3) 0.025(3) -0.004(2) 0.000(3) 0.007(3) N3 0.0205(15) 0.0176(15) 0.0202(15) 0.0055(10) 0.0018(9) 0.0015(9) N4 0.022(3) 0.006(3) 0.021(3) -0.003(2) -0.001(2) 0.000(2) N5 0.032(4) 0.011(3) 0.029(4) 0.001(3) 0.008(3) 0.009(3) N6 0.018(3) 0.015(3) 0.028(3) -0.007(3) -0.004(3) 0.004(2) N7 0.032(4) 0.030(4) 0.024(4) -0.008(3) -0.003(3) 0.010(3) N8 0.028(3) 0.015(3) 0.029(4) -0.006(3) -0.003(3) 0.001(3) N9 0.033(4) 0.032(4) 0.029(4) 0.000(3) -0.004(3) -0.012(3) N10 0.049(4) 0.024(4) 0.028(4) 0.006(3) 0.005(3) 0.016(3) N11 0.042(4) 0.027(4) 0.031(4) -0.011(3) -0.002(3) 0.009(3) N12 0.032(4) 0.025(4) 0.034(4) -0.002(3) -0.010(3) -0.004(3) N13 0.039(4) 0.018(3) 0.027(4) -0.007(3) -0.001(3) 0.004(3) N14 0.031(4) 0.036(4) 0.030(4) 0.002(3) -0.003(3) 0.012(3) N15 0.034(4) 0.028(4) 0.038(4) 0.001(3) 0.010(3) 0.014(3) N16 0.030(3) 0.003(3) 0.022(3) -0.003(2) -0.002(3) -0.001(2) N17 0.032(3) 0.005(3) 0.025(3) -0.004(2) -0.002(3) 0.004(2) N18 0.058(4) 0.004(3) 0.014(3) -0.002(2) 0.000(3) -0.001(3) N19 0.025(3) 0.008(3) 0.025(3) 0.003(2) 0.002(3) 0.007(2) N20 0.026(3) 0.005(3) 0.028(3) -0.007(2) -0.001(3) -0.002(2) O1 0.011(2) 0.023(3) 0.023(3) -0.001(2) -0.001(2) 0.004(2) O2 0.020(2) 0.011(2) 0.020(3) -0.002(2) -0.001(2) -0.0030(19) O3 0.026(3) 0.011(2) 0.026(3) -0.003(2) 0.002(2) 0.003(2) O4 0.029(3) 0.009(2) 0.028(3) -0.002(2) 0.001(2) 0.006(2) O5 0.042(3) 0.007(2) 0.028(3) -0.003(2) -0.002(2) 0.001(2) O6 0.037(3) 0.012(2) 0.025(3) -0.003(2) -0.005(2) 0.004(2) O7 0.015(2) 0.025(3) 0.022(3) 0.000(2) 0.001(2) 0.004(2) O8 0.014(2) 0.015(2) 0.024(3) 0.000(2) 0.000(2) -0.0031(19) P1 0.0202(9) 0.0048(8) 0.0197(9) -0.0023(7) 0.0003(7) 0.0022(6) P2 0.0274(10) 0.0038(8) 0.0212(9) -0.0011(7) 0.0032(8) 0.0046(7) P3 0.0204(9) 0.0066(8) 0.0185(9) -0.0028(7) 0.0011(7) 0.0032(7) P4 0.0251(10) 0.0104(9) 0.0234(10) -0.0044(7) -0.0001(8) 0.0046(7) P5 0.0276(11) 0.0179(10) 0.0239(10) -0.0057(8) -0.0042(8) 0.0050(8) P6 0.0313(11) 0.0181(10) 0.0242(10) -0.0043(8) 0.0039(9) 0.0090(8) P7 0.0361(12) 0.0195(10) 0.0236(11) -0.0049(8) -0.0050(9) 0.0025(9) P8 0.0343(12) 0.0215(10) 0.0270(11) -0.0016(8) 0.0016(9) 0.0048(9) P9 0.0310(11) 0.0127(9) 0.0241(10) -0.0049(8) -0.0006(8) 0.0031(8) P10 0.0184(9) 0.0060(8) 0.0211(9) -0.0030(7) 0.0004(7) -0.0001(7) P11 0.0197(9) 0.0042(8) 0.0200(9) -0.0019(7) -0.0012(7) 0.0024(6) P12 0.0294(10) 0.0034(8) 0.0217(10) -0.0006(7) -0.0014(8) 0.0001(7) Cl1 0.0354(11) 0.0144(8) 0.0408(11) 0.0080(8) 0.0119(9) 0.0031(7) Cl2 0.0242(9) 0.0245(9) 0.0303(10) 0.0043(8) 0.0061(8) 0.0051(7) Cl3 0.0529(14) 0.0482(14) 0.0296(11) 0.0054(10) -0.0040(10) 0.0202(11) Cl4 0.0424(12) 0.0229(10) 0.0377(12) 0.0045(9) 0.0033(9) 0.0121(9) Cl5 0.0545(14) 0.0299(11) 0.0423(13) 0.0030(10) -0.0055(11) -0.0069(10) Cl6 0.0623(16) 0.0445(14) 0.0421(13) 0.0165(11) 0.0110(12) 0.0076(12) Cl7 0.0207(9) 0.0250(9) 0.0298(10) 0.0039(8) -0.0041(7) 0.0007(7) Cl8 0.0307(10) 0.0150(8) 0.0378(11) 0.0079(8) -0.0062(8) 0.0031(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.473(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N4 1.488(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N5 1.491(9) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N5 1.485(10) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 O1 1.465(8) . ? C5 C6 1.528(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.522(10) . ? C6 C9 1.530(9) . ? C6 C7 1.547(9) . ? C7 O2 1.476(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O3 1.463(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O4 1.445(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N9 1.504(11) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N9 1.445(11) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N10 1.483(10) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N10 1.451(11) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N14 1.464(13) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N14 1.457(11) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N15 1.479(11) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N15 1.463(11) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O5 1.454(9) . ? C18 C19 1.525(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.513(10) . ? C19 C22 1.529(10) . ? C19 C21 1.535(11) . ? C20 O6 1.449(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O7 1.467(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O8 1.472(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N19 1.459(8) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 N19 1.473(9) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 N20 1.464(10) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N20 1.481(9) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 P1 1.587(6) . ? N1 P2 1.604(6) . ? N2 P2 1.589(6) . ? N2 P3 1.594(6) . ? N3 P3 1.585(6) . ? N3 P1 1.596(6) . ? N4 P1 1.636(6) . ? N5 P2 1.621(6) . ? N6 P4 1.583(6) . ? N6 P5 1.592(6) . ? N7 P6 1.568(7) . ? N7 P5 1.590(7) . ? N8 P4 1.572(7) . ? N8 P6 1.604(6) . ? N9 P5 1.643(7) . ? N10 P6 1.651(7) . ? N11 P8 1.580(8) . ? N11 P7 1.590(7) . ? N12 P9 1.581(8) . ? N12 P8 1.610(7) . ? N13 P9 1.570(7) . ? N13 P7 1.574(6) . ? N14 P7 1.664(7) . ? N15 P8 1.642(7) . ? N16 P10 1.588(6) . ? N16 P11 1.597(6) . ? N17 P11 1.592(6) . ? N17 P12 1.597(7) . ? N18 P12 1.581(6) . ? N18 P10 1.594(6) . ? N19 P11 1.655(6) . ? N20 P12 1.638(6) . ? O1 P3 1.593(5) . ? O2 P3 1.583(5) . ? O3 P4 1.587(5) . ? O4 P4 1.603(5) . ? O5 P9 1.607(6) . ? O6 P9 1.582(5) . ? O7 P10 1.590(5) . ? O8 P10 1.594(5) . ? P1 Cl2 2.052(3) . ? P2 Cl1 2.048(3) . ? P5 Cl3 2.080(3) . ? P6 Cl4 2.062(3) . ? P7 Cl5 2.048(3) . ? P8 Cl6 2.065(3) . ? P11 Cl7 2.057(3) . ? P12 Cl8 2.063(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 H1A 109.5 . . ? N4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C2 H2A 109.5 . . ? N4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N5 C3 H3A 109.5 . . ? N5 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N5 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N5 C4 H4A 109.5 . . ? N5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C5 C6 112.1(6) . . ? O1 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? O1 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C8 C6 C9 110.1(6) . . ? C8 C6 C5 106.9(6) . . ? C9 C6 C5 109.5(6) . . ? C8 C6 C7 109.6(6) . . ? C9 C6 C7 109.8(6) . . ? C5 C6 C7 110.8(5) . . ? O2 C7 C6 110.2(5) . . ? O2 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? O2 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O3 C8 C6 114.3(6) . . ? O3 C8 H8A 108.7 . . ? C6 C8 H8A 108.7 . . ? O3 C8 H8B 108.7 . . ? C6 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? O4 C9 C6 111.3(6) . . ? O4 C9 H9A 109.4 . . ? C6 C9 H9A 109.4 . . ? O4 C9 H9B 109.4 . . ? C6 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N9 C11 H11A 109.5 . . ? N9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N10 C12 H12A 109.5 . . ? N10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N10 C13 H13A 109.5 . . ? N10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N14 C14 H14A 109.5 . . ? N14 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N14 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N14 C15 H15A 109.5 . . ? N14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N15 C16 H16A 109.5 . . ? N15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N15 C17 H17A 109.5 . . ? N15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C18 C19 108.4(6) . . ? O5 C18 H18A 110.0 . . ? C19 C18 H18A 110.0 . . ? O5 C18 H18B 110.0 . . ? C19 C18 H18B 110.0 . . ? H18A C18 H18B 108.4 . . ? C20 C19 C18 110.7(6) . . ? C20 C19 C22 109.9(6) . . ? C18 C19 C22 112.1(6) . . ? C20 C19 C21 106.5(6) . . ? C18 C19 C21 107.0(6) . . ? C22 C19 C21 110.4(6) . . ? O6 C20 C19 113.9(6) . . ? O6 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? O6 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? O7 C21 C19 111.3(6) . . ? O7 C21 H21A 109.4 . . ? C19 C21 H21A 109.4 . . ? O7 C21 H21B 109.4 . . ? C19 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? O8 C22 C19 111.8(6) . . ? O8 C22 H22A 109.3 . . ? C19 C22 H22A 109.3 . . ? O8 C22 H22B 109.3 . . ? C19 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? N19 C23 H23A 109.5 . . ? N19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N19 C24 H24A 109.5 . . ? N19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N20 C25 H25A 109.5 . . ? N20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N20 C26 H26A 109.5 . . ? N20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? P1 N1 P2 118.2(4) . . ? P2 N2 P3 120.6(4) . . ? P3 N3 P1 121.0(4) . . ? C1 N4 C2 111.7(6) . . ? C1 N4 P1 118.0(5) . . ? C2 N4 P1 117.9(5) . . ? C4 N5 C3 113.0(6) . . ? C4 N5 P2 119.9(5) . . ? C3 N5 P2 117.2(5) . . ? P4 N6 P5 121.8(4) . . ? P6 N7 P5 120.9(4) . . ? P4 N8 P6 121.1(4) . . ? C11 N9 C10 111.3(7) . . ? C11 N9 P5 118.7(7) . . ? C10 N9 P5 117.8(6) . . ? C13 N10 C12 111.5(7) . . ? C13 N10 P6 118.0(6) . . ? C12 N10 P6 117.5(6) . . ? P8 N11 P7 120.0(4) . . ? P9 N12 P8 121.4(4) . . ? P9 N13 P7 122.1(4) . . ? C15 N14 C14 113.0(8) . . ? C15 N14 P7 117.3(6) . . ? C14 N14 P7 117.9(7) . . ? C17 N15 C16 114.7(8) . . ? C17 N15 P8 117.9(6) . . ? C16 N15 P8 116.6(6) . . ? P10 N16 P11 120.8(3) . . ? P11 N17 P12 117.8(4) . . ? P12 N18 P10 120.7(4) . . ? C23 N19 C24 113.0(6) . . ? C23 N19 P11 117.3(5) . . ? C24 N19 P11 116.0(5) . . ? C25 N20 C26 113.8(6) . . ? C25 N20 P12 119.4(5) . . ? C26 N20 P12 116.3(5) . . ? C5 O1 P3 114.1(4) . . ? C7 O2 P3 116.3(4) . . ? C8 O3 P4 116.1(4) . . ? C9 O4 P4 116.4(4) . . ? C18 O5 P9 117.6(5) . . ? C20 O6 P9 116.6(4) . . ? C21 O7 P10 113.8(4) . . ? C22 O8 P10 114.5(4) . . ? N1 P1 N3 118.3(3) . . ? N1 P1 N4 109.2(3) . . ? N3 P1 N4 109.7(3) . . ? N1 P1 Cl2 106.9(3) . . ? N3 P1 Cl2 107.4(2) . . ? N4 P1 Cl2 104.6(2) . . ? N2 P2 N1 118.1(3) . . ? N2 P2 N5 110.3(3) . . ? N1 P2 N5 111.0(3) . . ? N2 P2 Cl1 106.8(3) . . ? N1 P2 Cl1 104.6(2) . . ? N5 P2 Cl1 105.0(2) . . ? O2 P3 N3 108.7(3) . . ? O2 P3 O1 101.3(3) . . ? N3 P3 O1 108.7(3) . . ? O2 P3 N2 109.7(3) . . ? N3 P3 N2 118.6(3) . . ? O1 P3 N2 108.5(3) . . ? N8 P4 N6 118.1(3) . . ? N8 P4 O3 108.2(3) . . ? N6 P4 O3 109.1(3) . . ? N8 P4 O4 108.9(3) . . ? N6 P4 O4 109.0(3) . . ? O3 P4 O4 102.4(3) . . ? N7 P5 N6 118.2(3) . . ? N7 P5 N9 110.5(4) . . ? N6 P5 N9 109.7(4) . . ? N7 P5 Cl3 104.8(3) . . ? N6 P5 Cl3 108.1(3) . . ? N9 P5 Cl3 104.5(3) . . ? N7 P6 N8 119.0(4) . . ? N7 P6 N10 110.2(4) . . ? N8 P6 N10 109.7(4) . . ? N7 P6 Cl4 106.3(3) . . ? N8 P6 Cl4 106.7(3) . . ? N10 P6 Cl4 103.7(3) . . ? N13 P7 N11 119.3(4) . . ? N13 P7 N14 108.2(4) . . ? N11 P7 N14 111.4(4) . . ? N13 P7 Cl5 105.9(3) . . ? N11 P7 Cl5 104.9(3) . . ? N14 P7 Cl5 106.3(3) . . ? N11 P8 N12 118.3(4) . . ? N11 P8 N15 109.7(4) . . ? N12 P8 N15 109.4(4) . . ? N11 P8 Cl6 106.2(3) . . ? N12 P8 Cl6 107.9(3) . . ? N15 P8 Cl6 104.4(3) . . ? N13 P9 N12 118.0(4) . . ? N13 P9 O6 108.0(3) . . ? N12 P9 O6 110.0(3) . . ? N13 P9 O5 108.3(4) . . ? N12 P9 O5 109.5(3) . . ? O6 P9 O5 101.9(3) . . ? N16 P10 O7 108.4(3) . . ? N16 P10 O8 108.4(3) . . ? O7 P10 O8 101.7(3) . . ? N16 P10 N18 118.4(3) . . ? O7 P10 N18 109.4(3) . . ? O8 P10 N18 109.3(3) . . ? N17 P11 N16 118.1(3) . . ? N17 P11 N19 109.1(3) . . ? N16 P11 N19 109.0(3) . . ? N17 P11 Cl7 107.1(2) . . ? N16 P11 Cl7 107.7(2) . . ? N19 P11 Cl7 104.9(2) . . ? N18 P12 N17 118.3(3) . . ? N18 P12 N20 110.6(3) . . ? N17 P12 N20 111.0(3) . . ? N18 P12 Cl8 106.1(3) . . ? N17 P12 Cl8 104.5(2) . . ? N20 P12 Cl8 105.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C5 C6 C8 172.9(6) . . . . ? O1 C5 C6 C9 -67.8(7) . . . . ? O1 C5 C6 C7 53.5(8) . . . . ? C8 C6 C7 O2 -169.1(5) . . . . ? C9 C6 C7 O2 69.8(7) . . . . ? C5 C6 C7 O2 -51.3(7) . . . . ? C9 C6 C8 O3 51.2(8) . . . . ? C5 C6 C8 O3 170.1(6) . . . . ? C7 C6 C8 O3 -69.7(7) . . . . ? C8 C6 C9 O4 -53.3(8) . . . . ? C5 C6 C9 O4 -170.5(6) . . . . ? C7 C6 C9 O4 67.5(7) . . . . ? O5 C18 C19 C20 -55.5(8) . . . . ? O5 C18 C19 C22 67.6(8) . . . . ? O5 C18 C19 C21 -171.2(6) . . . . ? C18 C19 C20 O6 54.0(8) . . . . ? C22 C19 C20 O6 -70.3(7) . . . . ? C21 C19 C20 O6 170.1(6) . . . . ? C20 C19 C21 O7 173.2(5) . . . . ? C18 C19 C21 O7 -68.3(7) . . . . ? C22 C19 C21 O7 54.0(8) . . . . ? C20 C19 C22 O8 -169.7(5) . . . . ? C18 C19 C22 O8 66.7(8) . . . . ? C21 C19 C22 O8 -52.6(8) . . . . ? C6 C5 O1 P3 -60.3(7) . . . . ? C6 C7 O2 P3 58.4(6) . . . . ? C6 C8 O3 P4 -53.9(7) . . . . ? C6 C9 O4 P4 59.8(7) . . . . ? C19 C18 O5 P9 60.8(7) . . . . ? C19 C20 O6 P9 -54.0(7) . . . . ? C19 C21 O7 P10 -61.1(7) . . . . ? C19 C22 O8 P10 58.5(7) . . . . ? P2 N1 P1 N3 -25.4(6) . . . . ? P2 N1 P1 N4 -151.7(4) . . . . ? P2 N1 P1 Cl2 95.7(4) . . . . ? P3 N3 P1 N1 13.2(6) . . . . ? P3 N3 P1 N4 139.3(4) . . . . ? P3 N3 P1 Cl2 -107.6(4) . . . . ? C1 N4 P1 N1 168.9(5) . . . . ? C2 N4 P1 N1 -52.1(6) . . . . ? C1 N4 P1 N3 37.8(6) . . . . ? C2 N4 P1 N3 176.8(5) . . . . ? C1 N4 P1 Cl2 -77.0(5) . . . . ? C2 N4 P1 Cl2 61.9(5) . . . . ? P3 N2 P2 N1 -16.0(6) . . . . ? P3 N2 P2 N5 113.1(5) . . . . ? P3 N2 P2 Cl1 -133.3(4) . . . . ? P1 N1 P2 N2 26.8(6) . . . . ? P1 N1 P2 N5 -101.9(5) . . . . ? P1 N1 P2 Cl1 145.4(4) . . . . ? C4 N5 P2 N2 38.6(7) . . . . ? C3 N5 P2 N2 -177.9(5) . . . . ? C4 N5 P2 N1 171.4(6) . . . . ? C3 N5 P2 N1 -45.1(6) . . . . ? C4 N5 P2 Cl1 -76.2(6) . . . . ? C3 N5 P2 Cl1 67.4(6) . . . . ? C7 O2 P3 N3 -172.6(4) . . . . ? C7 O2 P3 O1 -58.2(5) . . . . ? C7 O2 P3 N2 56.3(5) . . . . ? P1 N3 P3 O2 -128.5(4) . . . . ? P1 N3 P3 O1 122.1(4) . . . . ? P1 N3 P3 N2 -2.3(6) . . . . ? C5 O1 P3 O2 57.9(5) . . . . ? C5 O1 P3 N3 172.3(4) . . . . ? C5 O1 P3 N2 -57.5(5) . . . . ? P2 N2 P3 O2 129.4(4) . . . . ? P2 N2 P3 N3 3.7(6) . . . . ? P2 N2 P3 O1 -120.8(4) . . . . ? P6 N8 P4 N6 8.6(6) . . . . ? P6 N8 P4 O3 133.1(4) . . . . ? P6 N8 P4 O4 -116.3(4) . . . . ? P5 N6 P4 N8 -3.9(6) . . . . ? P5 N6 P4 O3 -128.0(4) . . . . ? P5 N6 P4 O4 120.9(4) . . . . ? C8 O3 P4 N8 165.6(5) . . . . ? C8 O3 P4 N6 -64.7(5) . . . . ? C8 O3 P4 O4 50.7(5) . . . . ? C9 O4 P4 N8 -169.3(5) . . . . ? C9 O4 P4 N6 60.6(5) . . . . ? C9 O4 P4 O3 -54.9(5) . . . . ? P6 N7 P5 N6 7.7(7) . . . . ? P6 N7 P5 N9 135.2(5) . . . . ? P6 N7 P5 Cl3 -112.7(5) . . . . ? P4 N6 P5 N7 -4.1(6) . . . . ? P4 N6 P5 N9 -132.1(5) . . . . ? P4 N6 P5 Cl3 114.6(4) . . . . ? C11 N9 P5 N7 52.1(8) . . . . ? C10 N9 P5 N7 -168.7(6) . . . . ? C11 N9 P5 N6 -175.8(7) . . . . ? C10 N9 P5 N6 -36.6(7) . . . . ? C11 N9 P5 Cl3 -60.1(8) . . . . ? C10 N9 P5 Cl3 79.1(6) . . . . ? P5 N7 P6 N8 -3.2(7) . . . . ? P5 N7 P6 N10 124.7(5) . . . . ? P5 N7 P6 Cl4 -123.5(4) . . . . ? P4 N8 P6 N7 -5.1(7) . . . . ? P4 N8 P6 N10 -133.3(5) . . . . ? P4 N8 P6 Cl4 115.0(4) . . . . ? C13 N10 P6 N7 -178.1(6) . . . . ? C12 N10 P6 N7 43.9(7) . . . . ? C13 N10 P6 N8 -45.2(7) . . . . ? C12 N10 P6 N8 176.8(6) . . . . ? C13 N10 P6 Cl4 68.5(6) . . . . ? C12 N10 P6 Cl4 -69.6(6) . . . . ? P9 N13 P7 N11 0.9(7) . . . . ? P9 N13 P7 N14 -127.7(5) . . . . ? P9 N13 P7 Cl5 118.7(5) . . . . ? P8 N11 P7 N13 -9.4(7) . . . . ? P8 N11 P7 N14 117.8(5) . . . . ? P8 N11 P7 Cl5 -127.6(5) . . . . ? C15 N14 P7 N13 -171.9(7) . . . . ? C14 N14 P7 N13 -31.5(9) . . . . ? C15 N14 P7 N11 55.2(8) . . . . ? C14 N14 P7 N11 -164.4(8) . . . . ? C15 N14 P7 Cl5 -58.5(8) . . . . ? C14 N14 P7 Cl5 81.9(9) . . . . ? P7 N11 P8 N12 10.9(7) . . . . ? P7 N11 P8 N15 137.3(5) . . . . ? P7 N11 P8 Cl6 -110.5(5) . . . . ? P9 N12 P8 N11 -4.3(7) . . . . ? P9 N12 P8 N15 -130.8(5) . . . . ? P9 N12 P8 Cl6 116.2(5) . . . . ? C17 N15 P8 N11 -175.9(7) . . . . ? C16 N15 P8 N11 41.5(8) . . . . ? C17 N15 P8 N12 -44.6(8) . . . . ? C16 N15 P8 N12 172.8(7) . . . . ? C17 N15 P8 Cl6 70.7(7) . . . . ? C16 N15 P8 Cl6 -71.9(7) . . . . ? P7 N13 P9 N12 5.5(7) . . . . ? P7 N13 P9 O6 131.0(5) . . . . ? P7 N13 P9 O5 -119.5(5) . . . . ? P8 N12 P9 N13 -3.8(7) . . . . ? P8 N12 P9 O6 -128.2(5) . . . . ? P8 N12 P9 O5 120.6(5) . . . . ? C20 O6 P9 N13 163.0(5) . . . . ? C20 O6 P9 N12 -66.9(6) . . . . ? C20 O6 P9 O5 49.2(6) . . . . ? C18 O5 P9 N13 -168.5(5) . . . . ? C18 O5 P9 N12 61.7(5) . . . . ? C18 O5 P9 O6 -54.8(5) . . . . ? P11 N16 P10 O7 123.8(4) . . . . ? P11 N16 P10 O8 -126.5(4) . . . . ? P11 N16 P10 N18 -1.4(6) . . . . ? C21 O7 P10 N16 173.2(5) . . . . ? C21 O7 P10 O8 59.1(5) . . . . ? C21 O7 P10 N18 -56.4(5) . . . . ? C22 O8 P10 N16 -172.0(4) . . . . ? C22 O8 P10 O7 -57.8(5) . . . . ? C22 O8 P10 N18 57.7(5) . . . . ? P12 N18 P10 N16 3.2(7) . . . . ? P12 N18 P10 O7 -121.6(5) . . . . ? P12 N18 P10 O8 127.9(5) . . . . ? P12 N17 P11 N16 -26.4(6) . . . . ? P12 N17 P11 N19 -151.6(4) . . . . ? P12 N17 P11 Cl7 95.3(4) . . . . ? P10 N16 P11 N17 13.2(6) . . . . ? P10 N16 P11 N19 138.4(4) . . . . ? P10 N16 P11 Cl7 -108.2(4) . . . . ? C23 N19 P11 N17 167.9(5) . . . . ? C24 N19 P11 N17 -54.3(6) . . . . ? C23 N19 P11 N16 37.5(6) . . . . ? C24 N19 P11 N16 175.4(5) . . . . ? C23 N19 P11 Cl7 -77.6(5) . . . . ? C24 N19 P11 Cl7 60.3(5) . . . . ? P10 N18 P12 N17 -16.6(7) . . . . ? P10 N18 P12 N20 112.9(5) . . . . ? P10 N18 P12 Cl8 -133.4(4) . . . . ? P11 N17 P12 N18 28.2(6) . . . . ? P11 N17 P12 N20 -101.1(4) . . . . ? P11 N17 P12 Cl8 145.9(3) . . . . ? C25 N20 P12 N18 40.6(6) . . . . ? C26 N20 P12 N18 -176.8(5) . . . . ? C25 N20 P12 N17 173.9(5) . . . . ? C26 N20 P12 N17 -43.5(6) . . . . ? C25 N20 P12 Cl8 -73.6(6) . . . . ? C26 N20 P12 Cl8 69.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.763 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.195 # Attachment '2dnew.cif' data_2d _database_code_depnum_ccdc_archive 'CCDC 266982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H46 Cl4 N10 O4 P6' _chemical_formula_weight 806.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.440(4) _cell_length_b 8.0225(12) _cell_length_c 25.177(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.62(2) _cell_angle_gamma 90.00 _cell_volume 3675.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6493 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.625 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7054 _exptl_absorpt_correction_T_max 0.9876 _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 95mm CCD camera on \k-goniostat' _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 31050 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8044 _reflns_number_gt 5853 _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^)+(0.0924P)^2^+5.1364P] 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 8044 _refine_ls_number_parameters 396 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1872 _refine_ls_wR_factor_gt 0.1675 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.009 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 C14 C 0.50174(8) 0.58347(15) 0.21719(6) 0.327(7) Uani 1 1 d DU . . H14A H 0.5050 0.4732 0.2346 0.491 Uiso 1 1 calc R . . H14B H 0.5486 0.6102 0.2128 0.491 Uiso 1 1 calc R . . H14C H 0.4625 0.5832 0.1799 0.491 Uiso 1 1 calc R . . C15 C 0.48472(12) 0.71504(8) 0.25534(5) 0.272(6) Uani 1 1 d DU . . H15A H 0.5242 0.7145 0.2932 0.327 Uiso 1 1 calc R . . H15B H 0.4379 0.6866 0.2605 0.327 Uiso 1 1 calc R . . C16 C 0.47874(7) 0.89016(11) 0.22909(3) 0.267(6) Uani 1 1 d DU . . H16A H 0.5147 0.9645 0.2564 0.320 Uiso 1 1 calc R . . H16B H 0.4290 0.9350 0.2227 0.320 Uiso 1 1 calc R . . C17 C 0.49263(9) 0.89305(9) 0.17253(4) 0.254(6) Uani 1 1 d DU . . H17A H 0.4574 0.8186 0.1447 0.304 Uiso 1 1 calc R . . H17B H 0.5431 0.8538 0.1784 0.304 Uiso 1 1 calc R . . C18 C 0.48277(6) 1.07365(10) 0.15033(3) 0.430(9) Uani 1 1 d DU . . H18A H 0.4301 1.1039 0.1384 0.516 Uiso 1 1 calc R . . H18B H 0.5104 1.1493 0.1817 0.516 Uiso 1 1 calc R . . C19 C 0.50920(8) 1.1007(7) 0.10006(5) 0.281(6) Uani 1 1 d DU . . H19A H 0.5017 1.2175 0.0880 0.422 Uiso 1 1 calc R . . H19B H 0.4812 1.0285 0.0684 0.422 Uiso 1 1 calc R . . H19C H 0.5616 1.0733 0.1118 0.422 Uiso 1 1 calc R . . C1 C -0.20403(16) 0.3089(4) 0.27423(11) 0.0531(7) Uani 1 1 d . . . H1A H -0.2132 0.3486 0.3079 0.080 Uiso 1 1 calc R . . H1B H -0.1578 0.3563 0.2737 0.080 Uiso 1 1 calc R . . H1C H -0.2006 0.1870 0.2752 0.080 Uiso 1 1 calc R . . C2 C -0.33573(14) 0.2988(4) 0.22054(12) 0.0595(7) Uani 1 1 d . . . H2A H -0.3347 0.1767 0.2219 0.089 Uiso 1 1 calc R . . H2B H -0.3734 0.3356 0.1851 0.089 Uiso 1 1 calc R . . H2C H -0.3473 0.3421 0.2528 0.089 Uiso 1 1 calc R . . C3 C -0.41739(14) 0.3743(4) -0.01015(13) 0.0543(8) Uani 1 1 d . . . H3A H -0.4569 0.4573 -0.0224 0.081 Uiso 1 1 calc R . . H3B H -0.4190 0.3165 0.0237 0.081 Uiso 1 1 calc R . . H3C H -0.4239 0.2933 -0.0407 0.081 Uiso 1 1 calc R . . C4 C -0.33926(15) 0.5463(4) -0.04567(11) 0.0494(8) Uani 1 1 d . . . H4A H -0.3453 0.4671 -0.0766 0.074 Uiso 1 1 calc R . . H4B H -0.2907 0.5985 -0.0348 0.074 Uiso 1 1 calc R . . H4C H -0.3774 0.6324 -0.0583 0.074 Uiso 1 1 calc R . . C5 C -0.09876(11) 0.8492(3) 0.11639(9) 0.0307(5) Uani 1 1 d . . . H5A H -0.0748 0.9511 0.1368 0.037 Uiso 1 1 calc R . . H5B H -0.1423 0.8839 0.0838 0.037 Uiso 1 1 calc R . . C6 C -0.04481(11) 0.7564(3) 0.09440(8) 0.0260(5) Uani 1 1 d . . . C7 C -0.07773(12) 0.5888(3) 0.06862(9) 0.0333(5) Uani 1 1 d . . . H7A H -0.1203 0.6088 0.0334 0.040 Uiso 1 1 calc R . . H7B H -0.0405 0.5249 0.0585 0.040 Uiso 1 1 calc R . . C8 C 0.02879(12) 0.7272(3) 0.14195(9) 0.0311(5) Uani 1 1 d . . . H8A H 0.0203 0.6730 0.1744 0.037 Uiso 1 1 calc R . . H8B H 0.0592 0.6513 0.1283 0.037 Uiso 1 1 calc R . . C9 C -0.03473(12) 0.8565(3) 0.04642(9) 0.0301(5) Uani 1 1 d . . . H9A H -0.0056 0.7908 0.0285 0.036 Uiso 1 1 calc R . . H9B H -0.0833 0.8797 0.0172 0.036 Uiso 1 1 calc R . . C10 C 0.17555(12) 0.7873(3) -0.01305(9) 0.0345(6) Uani 1 1 d . . . H10A H 0.1655 0.8074 -0.0535 0.052 Uiso 1 1 calc R . . H10B H 0.1295 0.7610 -0.0072 0.052 Uiso 1 1 calc R . . H10C H 0.2097 0.6936 -0.0002 0.052 Uiso 1 1 calc R . . C11 C 0.27726(12) 0.9878(3) 0.01132(10) 0.0390(6) Uani 1 1 d . . . H11A H 0.3124 0.8952 0.0217 0.058 Uiso 1 1 calc R . . H11B H 0.2984 1.0843 0.0354 0.058 Uiso 1 1 calc R . . H11C H 0.2666 1.0174 -0.0285 0.058 Uiso 1 1 calc R . . C12 C 0.20146(19) 1.4366(4) 0.22295(12) 0.0659(9) Uani 1 1 d . . . H12A H 0.2281 1.4300 0.2640 0.099 Uiso 1 1 calc R . . H12B H 0.1502 1.4034 0.2145 0.099 Uiso 1 1 calc R . . H12C H 0.2031 1.5512 0.2100 0.099 Uiso 1 1 calc R . . C13 C 0.31155(16) 1.3713(4) 0.19940(12) 0.0560(9) Uani 1 1 d . . . H13A H 0.3107 1.4755 0.1789 0.084 Uiso 1 1 calc R . . H13B H 0.3332 1.2827 0.1835 0.084 Uiso 1 1 calc R . . H13C H 0.3410 1.3865 0.2396 0.084 Uiso 1 1 calc R . . N1 N -0.17204(11) 0.4693(3) 0.17581(8) 0.0385(5) Uani 1 1 d . . . N2 N -0.31651(11) 0.4235(3) 0.11365(9) 0.0446(6) Uani 1 1 d . . . N3 N -0.23137(10) 0.6166(3) 0.07326(8) 0.0378(5) Uani 1 1 d . . . N4 N 0.13077(9) 0.8902(2) 0.08501(8) 0.0307(5) Uani 1 1 d . . . N5 N 0.23036(10) 1.1414(2) 0.10584(9) 0.0386(5) Uani 1 1 d . . . N6 N 0.11221(10) 1.1680(2) 0.13990(8) 0.0366(5) Uani 1 1 d . . . N7 N -0.26441(11) 0.3608(3) 0.22324(8) 0.0429(5) Uani 1 1 d . . . N8 N -0.34600(10) 0.4580(3) 0.00327(9) 0.0390(5) Uani 1 1 d . . . N9 N 0.20843(9) 0.9373(2) 0.01946(8) 0.0308(5) Uani 1 1 d . . . N10 N 0.23581(12) 1.3246(3) 0.19358(8) 0.0431(6) Uani 1 1 d . . . O1 O -0.12223(8) 0.74593(18) 0.15423(6) 0.0314(4) Uani 1 1 d . . . O2 O -0.10128(8) 0.49170(19) 0.10734(6) 0.0324(4) Uani 1 1 d . . . O3 O 0.06812(8) 0.88427(19) 0.16065(6) 0.0312(4) Uani 1 1 d . . . O4 O 0.00291(8) 1.01374(19) 0.06775(6) 0.0308(4) Uani 1 1 d . . . P1 P -0.16122(3) 0.57688(8) 0.12745(2) 0.03144(14) Uani 1 1 d . . . P2 P -0.24583(3) 0.36898(8) 0.16473(2) 0.03769(15) Uani 1 1 d . . . P3 P -0.30944(3) 0.54382(8) 0.06604(3) 0.03603(15) Uani 1 1 d . . . P4 P 0.08292(3) 0.99286(7) 0.11338(2) 0.02819(13) Uani 1 1 d . . . P5 P 0.20580(3) 0.95833(7) 0.08321(2) 0.02812(13) Uani 1 1 d . . . P6 P 0.18323(3) 1.24676(7) 0.13346(2) 0.02939(14) Uani 1 1 d . . . Cl1 Cl -0.22457(4) 0.12567(8) 0.14890(3) 0.04908(16) Uani 1 1 d . . . Cl2 Cl -0.37705(3) 0.74337(8) 0.06365(3) 0.04768(17) Uani 1 1 d . . . Cl3 Cl 0.28766(3) 0.80478(8) 0.13264(3) 0.04264(16) Uani 1 1 d . . . Cl4 Cl 0.14702(3) 1.45229(7) 0.08241(2) 0.03705(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C14 0.193(6) 0.367(15) 0.483(13) -0.119(12) 0.195(7) 0.004(9) C15 0.233(9) 0.322(11) 0.243(9) 0.146(8) 0.059(8) 0.018(9) C16 0.086(4) 0.444(15) 0.198(8) 0.054(10) -0.041(5) -0.085(6) C17 0.059(3) 0.588(18) 0.105(4) 0.028(8) 0.019(3) 0.069(6) C18 0.237(9) 0.62(2) 0.315(16) 0.165(15) -0.054(10) -0.216(11) C19 0.260(7) 0.372(16) 0.272(8) 0.029(10) 0.168(6) -0.037(10) C1 0.0874(15) 0.0421(15) 0.0408(11) 0.0023(10) 0.0365(10) 0.0043(13) C2 0.0791(12) 0.0519(16) 0.0739(13) 0.0050(12) 0.0597(10) -0.0049(13) C3 0.0403(12) 0.0624(17) 0.0615(15) -0.0173(13) 0.0196(11) -0.0136(12) C4 0.0534(13) 0.0508(16) 0.0442(13) -0.0068(12) 0.0175(11) 0.0016(12) C5 0.0353(9) 0.0287(11) 0.0333(9) 0.0027(8) 0.0183(7) -0.0011(8) C6 0.0299(9) 0.0256(10) 0.0224(8) -0.0013(8) 0.0091(7) -0.0019(8) C7 0.0369(9) 0.0368(12) 0.0297(9) -0.0057(9) 0.0160(8) -0.0080(9) C8 0.0363(10) 0.0279(11) 0.0300(9) 0.0006(8) 0.0125(8) -0.0046(9) C9 0.0313(9) 0.0363(12) 0.0211(8) 0.0012(8) 0.0074(7) -0.0041(9) C10 0.0418(10) 0.0317(11) 0.0327(10) -0.0059(9) 0.0167(8) -0.0036(9) C11 0.0427(10) 0.0349(12) 0.0472(11) -0.0001(10) 0.0255(8) -0.0026(9) C12 0.104(2) 0.0607(17) 0.0341(12) -0.0227(12) 0.0260(13) -0.0223(16) C13 0.0556(16) 0.0495(16) 0.0417(14) 0.0038(13) -0.0093(13) -0.0158(13) N1 0.0502(9) 0.0360(10) 0.0349(8) 0.0014(8) 0.0221(7) -0.0071(8) N2 0.0479(9) 0.0464(12) 0.0472(10) 0.0025(9) 0.0262(8) -0.0105(9) N3 0.0386(9) 0.0412(11) 0.0354(9) 0.0074(8) 0.0152(7) -0.0053(8) N4 0.0358(8) 0.0241(9) 0.0359(8) -0.0043(7) 0.0172(7) -0.0043(7) N5 0.0373(8) 0.0239(9) 0.0595(11) -0.0093(8) 0.0230(8) -0.0065(7) N6 0.0458(9) 0.0298(9) 0.0418(9) -0.0111(8) 0.0249(7) -0.0075(8) N7 0.0699(10) 0.0318(10) 0.0400(8) -0.0008(8) 0.0355(7) -0.0029(9) N8 0.0362(9) 0.0381(11) 0.0441(10) -0.0045(8) 0.0159(8) -0.0006(8) N9 0.0342(8) 0.0268(9) 0.0321(8) -0.0006(7) 0.0126(7) -0.0024(7) N10 0.0652(12) 0.0345(10) 0.0245(8) -0.0004(8) 0.0093(8) -0.0097(10) O1 0.0445(7) 0.0254(7) 0.0311(6) -0.0014(6) 0.0218(5) -0.0050(6) O2 0.0410(7) 0.0277(8) 0.0337(6) -0.0031(6) 0.0198(5) -0.0055(6) O3 0.0366(7) 0.0333(8) 0.0231(6) 0.0012(6) 0.0098(5) -0.0056(6) O4 0.0336(7) 0.0317(8) 0.0275(6) 0.0057(6) 0.0111(5) -0.0002(6) P1 0.0402(2) 0.0292(3) 0.0297(2) 0.0004(2) 0.01819(19) -0.0047(2) P2 0.0547(3) 0.0288(3) 0.0421(2) -0.0005(2) 0.0326(2) -0.0055(2) P3 0.0369(2) 0.0361(3) 0.0400(3) -0.0007(2) 0.0196(2) -0.0039(2) P4 0.0355(2) 0.0258(3) 0.0253(2) -0.0016(2) 0.01321(19) -0.0035(2) P5 0.0304(2) 0.0217(3) 0.0324(2) -0.0026(2) 0.0111(2) -0.0018(2) P6 0.0389(3) 0.0222(3) 0.0267(2) -0.0045(2) 0.0110(2) -0.0041(2) Cl1 0.0799(3) 0.0313(3) 0.0540(3) -0.0049(2) 0.0459(2) -0.0034(3) Cl2 0.0482(3) 0.0438(3) 0.0549(3) -0.0084(3) 0.0230(2) 0.0040(3) Cl3 0.0439(3) 0.0393(3) 0.0375(3) 0.0017(2) 0.0054(2) 0.0096(2) Cl4 0.0497(3) 0.0329(3) 0.0274(2) 0.0032(2) 0.0121(2) 0.0036(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 C14 C15 1.5395(10) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.5396(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5400(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5404(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.5399(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C1 N7 1.462(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N7 1.452(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N8 1.470(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N8 1.466(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 O1 1.452(3) . ? C5 C6 1.539(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C9 1.520(3) . ? C6 C8 1.526(3) . ? C6 C7 1.532(3) . ? C7 O2 1.443(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O3 1.463(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O4 1.462(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N9 1.469(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N9 1.480(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N10 1.465(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N10 1.476(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 P1 1.566(2) . ? N1 P2 1.581(2) . ? N2 P2 1.577(2) . ? N2 P3 1.582(2) . ? N3 P3 1.576(2) . ? N3 P1 1.5852(19) . ? N4 P5 1.5733(19) . ? N4 P4 1.588(2) . ? N5 P6 1.577(2) . ? N5 P5 1.5869(19) . ? N6 P4 1.574(2) . ? N6 P6 1.578(2) . ? N7 P2 1.637(2) . ? N8 P3 1.639(2) . ? N9 P5 1.632(2) . ? N10 P6 1.624(2) . ? O1 P1 1.5838(15) . ? O2 P1 1.5799(18) . ? O3 P4 1.5809(17) . ? O4 P4 1.5840(15) . ? P2 Cl1 2.0629(9) . ? P3 Cl2 2.0586(10) . ? P5 Cl3 2.0503(9) . ? P6 Cl4 2.0565(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C14 C15 C16 110.98(10) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 113.55(9) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 108.04(7) . . ? C16 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? C16 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? C19 C18 C17 113.3(2) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? 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 . . ? N7 C1 H1A 109.5 . . ? N7 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N7 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N7 C2 H2A 109.5 . . ? N7 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N7 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N8 C3 H3A 109.5 . . ? N8 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N8 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N8 C4 H4A 109.5 . . ? N8 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N8 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C5 C6 111.78(17) . . ? O1 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? O1 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C9 C6 C8 110.92(18) . . ? C9 C6 C7 106.17(17) . . ? C8 C6 C7 109.49(17) . . ? C9 C6 C5 108.97(17) . . ? C8 C6 C5 111.20(17) . . ? C7 C6 C5 109.95(17) . . ? O2 C7 C6 111.84(18) . . ? O2 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? O2 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O3 C8 C6 111.05(17) . . ? O3 C8 H8A 109.4 . . ? C6 C8 H8A 109.4 . . ? O3 C8 H8B 109.4 . . ? C6 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O4 C9 C6 110.60(16) . . ? O4 C9 H9A 109.5 . . ? C6 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N9 C11 H11A 109.5 . . ? N9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N10 C12 H12A 109.5 . . ? N10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N10 C13 H13A 109.5 . . ? N10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? P1 N1 P2 120.34(12) . . ? P2 N2 P3 120.25(13) . . ? P3 N3 P1 121.76(13) . . ? P5 N4 P4 121.91(12) . . ? P6 N5 P5 120.43(13) . . ? P4 N6 P6 120.85(13) . . ? C2 N7 C1 113.7(2) . . ? C2 N7 P2 118.76(17) . . ? C1 N7 P2 115.99(19) . . ? C4 N8 C3 112.6(2) . . ? C4 N8 P3 118.07(17) . . ? C3 N8 P3 117.85(19) . . ? C10 N9 C11 112.61(19) . . ? C10 N9 P5 118.33(16) . . ? C11 N9 P5 116.79(14) . . ? C12 N10 C13 114.2(2) . . ? C12 N10 P6 117.20(18) . . ? C13 N10 P6 117.95(19) . . ? C5 O1 P1 115.04(13) . . ? C7 O2 P1 115.37(14) . . ? C8 O3 P4 116.45(13) . . ? C9 O4 P4 114.31(13) . . ? N1 P1 O2 109.08(10) . . ? N1 P1 O1 108.43(10) . . ? O2 P1 O1 102.15(9) . . ? N1 P1 N3 118.01(11) . . ? O2 P1 N3 108.62(10) . . ? O1 P1 N3 109.38(10) . . ? N2 P2 N1 118.58(11) . . ? N2 P2 N7 109.87(12) . . ? N1 P2 N7 109.59(11) . . ? N2 P2 Cl1 106.33(9) . . ? N1 P2 Cl1 106.54(9) . . ? N7 P2 Cl1 105.00(8) . . ? N3 P3 N2 118.41(11) . . ? N3 P3 N8 109.86(12) . . ? N2 P3 N8 110.52(12) . . ? N3 P3 Cl2 107.11(9) . . ? N2 P3 Cl2 105.77(9) . . ? N8 P3 Cl2 104.06(8) . . ? N6 P4 O3 107.89(10) . . ? N6 P4 O4 109.23(9) . . ? O3 P4 O4 102.22(9) . . ? N6 P4 N4 118.19(11) . . ? O3 P4 N4 110.09(10) . . ? O4 P4 N4 108.04(9) . . ? N4 P5 N5 118.42(11) . . ? N4 P5 N9 110.04(10) . . ? N5 P5 N9 109.83(11) . . ? N4 P5 Cl3 107.64(7) . . ? N5 P5 Cl3 105.49(7) . . ? N9 P5 Cl3 104.38(7) . . ? N5 P6 N6 119.74(11) . . ? N5 P6 N10 110.16(11) . . ? N6 P6 N10 110.16(12) . . ? N5 P6 Cl4 106.15(9) . . ? N6 P6 Cl4 105.42(8) . . ? N10 P6 Cl4 103.82(8) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.811 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.108