# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 900074' #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H48 Cu2 N2 O24 P6' _chemical_formula_weight 1133.60 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' Cu Cu 0.3201 1.2651 '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 7.5069(5) _cell_length_b 12.8076(10) _cell_length_c 22.2479(17) _cell_angle_alpha 93.887(4) _cell_angle_beta 94.965(4) _cell_angle_gamma 92.390(4) _cell_volume 2123.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2278 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 25 _exptl_crystal_description Plate _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 1.320 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15199 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7398 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1163P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7398 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1371 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.2146 _refine_ls_wR_factor_gt 0.1740 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.40667(12) 0.70250(7) 0.78060(4) 0.0250(3) Uani 1 1 d . . . Cu2 Cu -0.05366(12) 0.18514(7) 0.27758(4) 0.0250(3) Uani 1 1 d . . . O1W O 0.0440(8) 0.1761(5) 0.1980(3) 0.0476(17) Uani 1 1 d . . . H1W H 0.0383 0.2400 0.1902 0.057 Uiso 1 1 d R . . H2W H 0.1333 0.1375 0.2002 0.057 Uiso 1 1 d R . . O1 O 0.7633(8) 0.5848(4) 1.1889(3) 0.0454(16) Uani 1 1 d . . . O2W O 0.5271(8) 0.6830(4) 0.7053(3) 0.0426(16) Uani 1 1 d . . . H3W H 0.5371 0.7439 0.6925 0.051 Uiso 1 1 d R . . H4W H 0.6143 0.6441 0.7001 0.051 Uiso 1 1 d R . . O2 O 0.5921(8) 0.4983(5) 1.0972(3) 0.0478(17) Uani 1 1 d . . . H2B H 0.5335 0.4432 1.0879 0.072 Uiso 1 1 calc R . . O3 O 0.5352(8) 0.4368(4) 1.2024(3) 0.0415(15) Uani 1 1 d . . . O3W O 0.1238(13) 0.3437(7) 0.1328(4) 0.123(4) Uani 1 1 d . . . H5W H 0.0932 0.2944 0.1059 0.148 Uiso 1 1 d R . . H6W H 0.0681 0.3933 0.1174 0.148 Uiso 1 1 d R . . O4 O 0.5052(7) 0.9873(4) 1.2687(2) 0.0299(13) Uani 1 1 d . . . H4B H 0.4028 0.9613 1.2643 0.045 Uiso 1 1 calc R . . O4W O -0.4818(9) 0.1731(5) 0.3782(3) 0.0589(19) Uani 1 1 d . . . H7W H -0.4232 0.1184 0.3729 0.071 Uiso 1 1 d R . . H8W H -0.5843 0.1427 0.3690 0.071 Uiso 1 1 d R . . O5 O 0.3594(7) 1.0845(4) 1.1827(2) 0.0263(12) Uani 1 1 d . . . O5W O 0.3128(17) 0.0026(8) 0.5255(5) 0.157(5) Uani 1 1 d . . . H9W H 0.2818 0.0317 0.5582 0.188 Uiso 1 1 d R . . H10W H 0.4095 -0.0159 0.5437 0.188 Uiso 1 1 d R . . O6 O 0.6474(6) 1.1557(4) 1.2430(2) 0.0225(12) Uani 1 1 d . . . O6W O -0.0671(13) 0.4609(8) 0.0510(5) 0.132(4) Uani 1 1 d . . . H11W H -0.1604 0.4917 0.0390 0.159 Uiso 1 1 d R . . H12W H -0.0110 0.5163 0.0671 0.159 Uiso 1 1 d R . . O7 O 0.5740(7) 0.6646(4) 0.9414(2) 0.0402(15) Uani 1 1 d . . . O8 O 0.6114(8) 0.8537(5) 0.9225(3) 0.0475(17) Uani 1 1 d . . . H8C H 0.6159 0.8707 0.8877 0.071 Uiso 1 1 calc R . . O9 O 0.3587(7) 0.7415(4) 0.8631(2) 0.0353(14) Uani 1 1 d . . . O10 O -0.2111(8) 0.0086(4) 0.6226(3) 0.0418(15) Uani 1 1 d . . . H10A H -0.1566 -0.0340 0.6030 0.063 Uiso 1 1 calc R . . O11 O -0.2130(7) 0.1197(4) 0.7164(2) 0.0330(13) Uani 1 1 d . . . O12 O -0.0338(8) -0.0462(4) 0.7179(2) 0.0398(15) Uani 1 1 d . . . O13 O -0.0272(7) 0.4946(4) 0.7565(2) 0.0369(14) Uani 1 1 d . . . H13B H 0.0656 0.4723 0.7719 0.055 Uiso 1 1 calc R . . O14 O -0.1575(7) 0.5958(4) 0.6750(2) 0.0327(14) Uani 1 1 d . . . O15 O 0.1216(7) 0.6701(4) 0.7385(2) 0.0268(12) Uani 1 1 d . . . O16 O 0.0797(10) 0.1227(5) 0.4470(3) 0.063(2) Uani 1 1 d . . . O17 O 0.1697(8) 0.2999(6) 0.4183(3) 0.064(2) Uani 1 1 d . . . H17C H 0.1546 0.3299 0.3869 0.096 Uiso 1 1 calc R . . O18 O -0.1035(7) 0.2061(4) 0.3623(2) 0.0348(14) Uani 1 1 d . . . N1 N -0.3847(9) 0.2523(6) 0.6388(3) 0.0384(18) Uani 1 1 d . . . H0A H -0.3397 0.2063 0.6683 0.046 Uiso 1 1 d R . . N2 N 0.9163(10) 0.7251(6) 1.1213(3) 0.0416(19) Uani 1 1 d . . . H0B H 0.8855 0.6657 1.1431 0.050 Uiso 1 1 d R . . P1 P 0.5873(3) 0.52817(18) 1.16668(10) 0.0343(6) Uani 1 1 d . . . P2 P 0.5346(3) 1.05980(15) 1.21592(9) 0.0213(5) Uani 1 1 d . . . P3 P 0.4735(3) 0.75742(18) 0.92272(9) 0.0298(5) Uani 1 1 d . . . P4 P -0.0962(3) 0.04503(16) 0.68324(10) 0.0288(5) Uani 1 1 d . . . P5 P 0.0185(3) 0.57281(16) 0.70855(9) 0.0250(5) Uani 1 1 d . . . P6 P 0.0089(3) 0.22128(18) 0.42265(9) 0.0325(6) Uani 1 1 d . . . C1 C 0.4402(12) 0.7134(6) 1.1368(4) 0.034(2) Uani 1 1 d . . . C2 C 0.5347(11) 0.8033(6) 1.1643(4) 0.034(2) Uani 1 1 d . . . H2A H 0.5779 0.8038 1.2048 0.041 Uiso 1 1 calc R . . C3 C 0.5658(11) 0.8908(6) 1.1335(3) 0.0286(19) Uani 1 1 d . . . C4 C 0.4972(10) 0.8896(6) 1.0724(3) 0.0270(18) Uani 1 1 d . . . H4A H 0.5138 0.9484 1.0508 0.032 Uiso 1 1 calc R . . C5 C 0.4040(11) 0.7995(6) 1.0441(3) 0.0291(19) Uani 1 1 d . . . C6 C 0.3766(11) 0.7127(6) 1.0766(4) 0.035(2) Uani 1 1 d . . . H6A H 0.3147 0.6533 1.0577 0.042 Uiso 1 1 calc R . . C7 C 0.4089(12) 0.6167(7) 1.1722(4) 0.042(2) Uani 1 1 d . . . H7A H 0.2965 0.5807 1.1565 0.051 Uiso 1 1 calc R . . H7B H 0.4001 0.6387 1.2143 0.051 Uiso 1 1 calc R . . C8 C 0.6656(11) 0.9883(6) 1.1647(3) 0.0291(19) Uani 1 1 d . . . H8A H 0.7005 1.0339 1.1343 0.035 Uiso 1 1 calc R . . H8B H 0.7740 0.9678 1.1870 0.035 Uiso 1 1 calc R . . C9 C 0.3272(11) 0.7963(7) 0.9781(3) 0.031(2) Uani 1 1 d . . . H9A H 0.2877 0.8656 0.9700 0.038 Uiso 1 1 calc R . . H9B H 0.2222 0.7488 0.9730 0.038 Uiso 1 1 calc R . . C10 C 0.0741(10) 0.2128(6) 0.6323(3) 0.0275(19) Uani 1 1 d . . . C11 C 0.1264(10) 0.3120(6) 0.6587(3) 0.0276(19) Uani 1 1 d . . . H11A H 0.1805 0.3181 0.6981 0.033 Uiso 1 1 calc R . . C12 C 0.1012(10) 0.4018(6) 0.6287(3) 0.0255(18) Uani 1 1 d . . . C13 C 0.0207(10) 0.3912(6) 0.5694(3) 0.0257(18) Uani 1 1 d . . . H13A H 0.0043 0.4508 0.5482 0.031 Uiso 1 1 calc R . . C14 C -0.0349(10) 0.2948(6) 0.5416(3) 0.0261(18) Uani 1 1 d . . . C15 C -0.0083(10) 0.2062(6) 0.5732(3) 0.0256(18) Uani 1 1 d . . . H15A H -0.0462 0.1408 0.5547 0.031 Uiso 1 1 calc R . . C16 C 0.1029(10) 0.1146(6) 0.6655(3) 0.033(2) Uani 1 1 d . . . H16A H 0.1766 0.1337 0.7029 0.040 Uiso 1 1 calc R . . H16B H 0.1696 0.0673 0.6410 0.040 Uiso 1 1 calc R . . C17 C 0.1639(10) 0.5092(6) 0.6589(3) 0.0280(19) Uani 1 1 d . . . H17A H 0.1852 0.5555 0.6272 0.034 Uiso 1 1 calc R . . H17B H 0.2780 0.5019 0.6818 0.034 Uiso 1 1 calc R . . C18 C -0.1252(10) 0.2798(6) 0.4770(3) 0.0297(19) Uani 1 1 d . . . H18A H -0.1591 0.3477 0.4641 0.036 Uiso 1 1 calc R . . H18B H -0.2342 0.2365 0.4774 0.036 Uiso 1 1 calc R . . C19 C -0.5321(11) 0.4520(6) 0.5018(4) 0.039(2) Uani 1 1 d . . . H19A H -0.6115 0.4242 0.4698 0.047 Uiso 1 1 calc R . . C20 C -0.4921(10) 0.3839(6) 0.5511(4) 0.0297(19) Uani 1 1 d . . . C21 C -0.5323(11) 0.2769(7) 0.5429(4) 0.040(2) Uani 1 1 d . . . H21A H -0.5954 0.2487 0.5073 0.048 Uiso 1 1 calc R . . C22 C -0.4780(12) 0.2116(7) 0.5883(4) 0.040(2) Uani 1 1 d . . . H22A H -0.5069 0.1400 0.5832 0.048 Uiso 1 1 calc R . . C23 C -0.3509(11) 0.3548(7) 0.6492(4) 0.038(2) Uani 1 1 d . . . H23A H -0.2897 0.3810 0.6856 0.046 Uiso 1 1 calc R . . C24 C -0.4050(11) 0.4222(7) 0.6070(4) 0.039(2) Uani 1 1 d . . . H24A H -0.3840 0.4940 0.6155 0.046 Uiso 1 1 calc R . . C25 C 1.0315(12) 0.9904(8) 1.0277(4) 0.044(2) Uani 1 1 d . . . H25A H 1.1056 1.0425 1.0493 0.052 Uiso 1 1 calc R . . C26 C 0.9960(10) 0.8954(6) 1.0582(4) 0.0283(19) Uani 1 1 d . . . C27 C 0.9007(11) 0.8066(7) 1.0311(4) 0.041(2) Uani 1 1 d . . . H27A H 0.8677 0.8032 0.9897 0.050 Uiso 1 1 calc R . . C28 C 0.8545(11) 0.7253(7) 1.0628(4) 0.041(2) Uani 1 1 d . . . H28A H 0.7808 0.6699 1.0444 0.049 Uiso 1 1 calc R . . C29 C 1.0171(12) 0.8046(7) 1.1509(4) 0.040(2) Uani 1 1 d . . . H29A H 1.0579 0.8009 1.1913 0.048 Uiso 1 1 calc R . . C30 C 1.0612(11) 0.8945(7) 1.1202(4) 0.039(2) Uani 1 1 d . . . H30A H 1.1300 0.9508 1.1399 0.046 Uiso 1 1 calc R . . 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 Cu1 0.0370(6) 0.0256(6) 0.0128(5) 0.0043(4) 0.0035(4) -0.0013(4) Cu2 0.0341(6) 0.0283(6) 0.0133(5) 0.0041(4) 0.0035(4) 0.0005(4) O1W 0.057(4) 0.051(4) 0.043(4) 0.021(3) 0.026(3) 0.030(3) O1 0.050(4) 0.046(4) 0.041(4) 0.011(3) 0.002(3) -0.001(3) O2W 0.056(4) 0.033(3) 0.044(4) 0.011(3) 0.017(3) 0.017(3) O2 0.070(4) 0.046(4) 0.028(4) 0.005(3) 0.011(3) -0.001(3) O3 0.063(4) 0.029(3) 0.035(4) 0.013(3) 0.011(3) 0.003(3) O3W 0.166(9) 0.109(7) 0.121(8) 0.085(6) 0.084(7) 0.055(7) O4 0.038(3) 0.034(3) 0.018(3) 0.010(2) 0.004(2) -0.006(3) O4W 0.060(4) 0.081(5) 0.037(4) 0.012(4) 0.010(3) 0.001(4) O5 0.032(3) 0.028(3) 0.019(3) 0.001(2) 0.008(2) -0.003(2) O5W 0.236(15) 0.126(9) 0.093(9) -0.006(7) -0.046(9) -0.023(9) O6 0.026(3) 0.027(3) 0.013(3) -0.001(2) -0.001(2) -0.001(2) O6W 0.117(8) 0.145(9) 0.153(10) 0.062(8) 0.060(7) 0.042(7) O7 0.039(3) 0.056(4) 0.024(3) -0.003(3) -0.001(3) 0.005(3) O8 0.051(4) 0.067(4) 0.021(3) 0.011(3) -0.003(3) -0.029(3) O9 0.036(3) 0.053(4) 0.017(3) 0.007(3) 0.002(2) -0.003(3) O10 0.047(4) 0.048(4) 0.029(4) -0.002(3) 0.001(3) 0.005(3) O11 0.038(3) 0.039(3) 0.024(3) 0.006(3) 0.014(3) 0.006(3) O12 0.062(4) 0.035(3) 0.026(3) 0.010(3) 0.011(3) 0.015(3) O13 0.043(3) 0.039(3) 0.031(4) 0.013(3) 0.011(3) -0.002(3) O14 0.031(3) 0.041(3) 0.025(3) 0.001(3) -0.002(3) -0.002(3) O15 0.031(3) 0.032(3) 0.016(3) 0.000(2) -0.001(2) -0.008(2) O16 0.098(6) 0.075(5) 0.017(4) 0.000(3) 0.003(3) 0.044(4) O17 0.041(4) 0.124(6) 0.024(4) 0.012(4) 0.003(3) -0.024(4) O18 0.036(3) 0.056(4) 0.012(3) -0.001(3) 0.000(2) -0.007(3) N1 0.033(4) 0.049(5) 0.036(5) 0.017(4) 0.008(3) 0.007(4) N2 0.049(5) 0.035(4) 0.042(5) 0.014(4) -0.001(4) -0.002(4) P1 0.0470(14) 0.0347(13) 0.0223(13) 0.0050(10) 0.0067(10) 0.0040(11) P2 0.0264(11) 0.0248(11) 0.0126(10) 0.0010(8) 0.0033(8) -0.0021(9) P3 0.0340(12) 0.0426(14) 0.0125(11) 0.0011(10) 0.0014(9) -0.0010(10) P4 0.0381(12) 0.0310(12) 0.0192(12) 0.0064(9) 0.0074(9) 0.0067(10) P5 0.0314(12) 0.0261(11) 0.0169(11) -0.0019(9) 0.0033(9) -0.0027(9) P6 0.0376(13) 0.0492(15) 0.0104(11) -0.0005(10) 0.0024(9) 0.0012(11) C1 0.057(6) 0.025(5) 0.021(5) 0.008(4) 0.006(4) 0.008(4) C2 0.049(5) 0.033(5) 0.019(5) -0.001(4) -0.001(4) 0.005(4) C3 0.045(5) 0.022(4) 0.018(5) 0.002(3) 0.000(4) -0.001(4) C4 0.045(5) 0.019(4) 0.019(5) 0.002(3) 0.013(4) 0.008(4) C5 0.040(5) 0.036(5) 0.012(4) 0.004(4) 0.007(4) 0.010(4) C6 0.049(5) 0.033(5) 0.023(5) 0.002(4) 0.005(4) 0.003(4) C7 0.056(6) 0.055(6) 0.016(5) -0.003(4) 0.006(4) 0.009(5) C8 0.040(5) 0.032(5) 0.015(4) 0.004(4) 0.003(4) 0.003(4) C9 0.041(5) 0.045(5) 0.007(4) 0.006(4) -0.001(3) -0.002(4) C10 0.029(4) 0.037(5) 0.018(4) -0.001(4) 0.013(3) 0.005(4) C11 0.028(4) 0.045(5) 0.010(4) -0.001(4) 0.004(3) 0.001(4) C12 0.033(4) 0.030(5) 0.012(4) -0.006(3) 0.004(3) -0.002(4) C13 0.034(4) 0.030(5) 0.015(4) 0.008(3) 0.004(3) 0.004(4) C14 0.036(5) 0.034(5) 0.009(4) -0.001(3) 0.004(3) 0.008(4) C15 0.036(5) 0.030(5) 0.010(4) -0.003(3) 0.003(3) -0.003(4) C16 0.036(5) 0.049(5) 0.018(5) 0.012(4) 0.007(4) 0.012(4) C17 0.033(5) 0.031(5) 0.019(4) -0.003(4) 0.006(4) -0.006(4) C18 0.034(5) 0.041(5) 0.014(4) 0.004(4) 0.003(3) -0.002(4) C19 0.033(5) 0.044(5) 0.039(6) 0.007(5) -0.008(4) 0.000(4) C20 0.022(4) 0.042(5) 0.024(5) 0.007(4) -0.002(3) -0.003(4) C21 0.042(5) 0.045(6) 0.031(5) -0.008(4) 0.002(4) -0.002(4) C22 0.050(6) 0.038(5) 0.034(6) 0.004(4) 0.009(5) -0.002(4) C23 0.038(5) 0.051(6) 0.025(5) 0.002(4) 0.005(4) 0.001(4) C24 0.034(5) 0.042(5) 0.039(6) 0.004(4) 0.002(4) 0.005(4) C25 0.035(5) 0.052(6) 0.045(6) 0.006(5) 0.009(4) -0.002(4) C26 0.029(4) 0.026(4) 0.031(5) 0.007(4) 0.006(4) -0.004(4) C27 0.040(5) 0.063(6) 0.021(5) 0.000(4) 0.009(4) -0.014(5) C28 0.037(5) 0.053(6) 0.034(6) 0.014(5) 0.004(4) -0.007(4) C29 0.044(5) 0.052(6) 0.025(5) 0.012(4) 0.004(4) 0.000(5) C30 0.035(5) 0.041(5) 0.039(6) -0.008(4) 0.005(4) 0.000(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.909(5) 2_667 ? Cu1 O9 1.938(5) . ? Cu1 O6 1.973(5) 2_677 ? Cu1 O2W 1.978(6) . ? Cu1 O15 2.270(5) . ? Cu2 O12 1.928(5) 2_556 ? Cu2 O18 1.957(5) . ? Cu2 O1W 1.972(6) . ? Cu2 O15 1.991(5) 2_566 ? Cu2 O6 2.315(5) 1_444 ? O1 P1 1.509(6) . ? O2 P1 1.571(6) . ? O3 P1 1.516(5) . ? O3 Cu1 1.909(5) 2_667 ? O4 P2 1.570(5) . ? O5 P2 1.508(5) . ? O6 P2 1.521(5) . ? O6 Cu1 1.973(5) 2_677 ? O6 Cu2 2.315(5) 1_666 ? O7 P3 1.498(6) . ? O8 P3 1.577(6) . ? O9 P3 1.514(5) . ? O10 P4 1.569(6) . ? O11 P4 1.521(5) . ? O12 P4 1.512(5) . ? O12 Cu2 1.928(5) 2_556 ? O13 P5 1.562(5) . ? O14 P5 1.510(5) . ? O15 P5 1.521(5) . ? O15 Cu2 1.991(5) 2_566 ? O16 P6 1.506(6) . ? O17 P6 1.554(6) . ? O18 P6 1.518(5) . ? N1 C23 1.327(10) . ? N1 C22 1.335(10) . ? N2 C29 1.342(10) . ? N2 C28 1.344(10) . ? P1 C7 1.797(9) . ? P2 C8 1.797(8) . ? P3 C9 1.780(8) . ? P4 C16 1.795(8) . ? P5 C17 1.799(8) . ? P6 C18 1.786(8) . ? C1 C6 1.382(10) . ? C1 C2 1.403(11) . ? C1 C7 1.533(11) . ? C2 C3 1.374(10) . ? C3 C4 1.411(10) . ? C3 C8 1.522(10) . ? C4 C5 1.405(11) . ? C5 C6 1.384(11) . ? C5 C9 1.527(10) . ? C10 C11 1.390(10) . ? C10 C15 1.398(10) . ? C10 C16 1.515(10) . ? C11 C12 1.381(10) . ? C12 C13 1.399(10) . ? C12 C17 1.526(10) . ? C13 C14 1.374(10) . ? C14 C15 1.388(10) . ? C14 C18 1.532(10) . ? C19 C19 1.313(16) 2_466 ? C19 C20 1.465(11) . ? C20 C21 1.387(11) . ? C20 C24 1.402(11) . ? C21 C22 1.399(11) . ? C23 C24 1.364(11) . ? C25 C25 1.325(17) 2_777 ? C25 C26 1.458(11) . ? C26 C27 1.391(11) . ? C26 C30 1.424(11) . ? C27 C28 1.347(11) . ? C29 C30 1.419(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O9 93.7(2) 2_667 . ? O3 Cu1 O6 175.7(2) 2_667 2_677 ? O9 Cu1 O6 90.5(2) . 2_677 ? O3 Cu1 O2W 88.2(2) 2_667 . ? O9 Cu1 O2W 162.6(2) . . ? O6 Cu1 O2W 87.5(2) 2_677 . ? O3 Cu1 O15 99.2(2) 2_667 . ? O9 Cu1 O15 99.4(2) . . ? O6 Cu1 O15 80.60(19) 2_677 . ? O2W Cu1 O15 97.3(2) . . ? O12 Cu2 O18 96.8(2) 2_556 . ? O12 Cu2 O1W 83.2(2) 2_556 . ? O18 Cu2 O1W 168.6(2) . . ? O12 Cu2 O15 170.8(2) 2_556 2_566 ? O18 Cu2 O15 91.6(2) . 2_566 ? O1W Cu2 O15 87.8(2) . 2_566 ? O12 Cu2 O6 103.8(2) 2_556 1_444 ? O18 Cu2 O6 93.6(2) . 1_444 ? O1W Cu2 O6 97.4(2) . 1_444 ? O15 Cu2 O6 79.10(19) 2_566 1_444 ? P1 O3 Cu1 143.3(4) . 2_667 ? P2 O6 Cu1 121.2(3) . 2_677 ? P2 O6 Cu2 133.9(3) . 1_666 ? Cu1 O6 Cu2 99.4(2) 2_677 1_666 ? P3 O9 Cu1 134.2(3) . . ? P4 O12 Cu2 152.4(4) . 2_556 ? P5 O15 Cu2 122.8(3) . 2_566 ? P5 O15 Cu1 133.8(3) . . ? Cu2 O15 Cu1 100.4(2) 2_566 . ? P6 O18 Cu2 135.4(3) . . ? C23 N1 C22 121.7(8) . . ? C29 N2 C28 123.0(8) . . ? O1 P1 O3 115.1(3) . . ? O1 P1 O2 107.5(4) . . ? O3 P1 O2 113.7(3) . . ? O1 P1 C7 109.6(4) . . ? O3 P1 C7 105.1(4) . . ? O2 P1 C7 105.5(4) . . ? O5 P2 O6 114.3(3) . . ? O5 P2 O4 111.5(3) . . ? O6 P2 O4 107.3(3) . . ? O5 P2 C8 109.3(3) . . ? O6 P2 C8 107.8(3) . . ? O4 P2 C8 106.4(3) . . ? O7 P3 O9 115.6(3) . . ? O7 P3 O8 108.4(3) . . ? O9 P3 O8 110.9(3) . . ? O7 P3 C9 110.5(4) . . ? O9 P3 C9 106.2(3) . . ? O8 P3 C9 104.6(4) . . ? O12 P4 O11 115.3(3) . . ? O12 P4 O10 112.4(3) . . ? O11 P4 O10 104.7(3) . . ? O12 P4 C16 106.1(3) . . ? O11 P4 C16 109.7(4) . . ? O10 P4 C16 108.5(4) . . ? O14 P5 O15 113.6(3) . . ? O14 P5 O13 106.3(3) . . ? O15 P5 O13 110.9(3) . . ? O14 P5 C17 111.4(3) . . ? O15 P5 C17 106.9(3) . . ? O13 P5 C17 107.7(3) . . ? O16 P6 O18 115.2(4) . . ? O16 P6 O17 108.4(4) . . ? O18 P6 O17 110.2(3) . . ? O16 P6 C18 108.0(4) . . ? O18 P6 C18 108.2(3) . . ? O17 P6 C18 106.5(4) . . ? C6 C1 C2 118.8(7) . . ? C6 C1 C7 120.1(8) . . ? C2 C1 C7 121.0(7) . . ? C3 C2 C1 122.2(7) . . ? C2 C3 C4 118.3(7) . . ? C2 C3 C8 121.3(7) . . ? C4 C3 C8 120.4(7) . . ? C5 C4 C3 120.0(7) . . ? C6 C5 C4 120.0(7) . . ? C6 C5 C9 118.9(7) . . ? C4 C5 C9 121.1(7) . . ? C1 C6 C5 120.7(8) . . ? C1 C7 P1 111.5(6) . . ? C3 C8 P2 112.9(6) . . ? C5 C9 P3 116.5(6) . . ? C11 C10 C15 117.5(7) . . ? C11 C10 C16 122.1(7) . . ? C15 C10 C16 120.4(7) . . ? C12 C11 C10 122.5(7) . . ? C11 C12 C13 118.0(7) . . ? C11 C12 C17 120.9(7) . . ? C13 C12 C17 121.1(7) . . ? C14 C13 C12 121.5(7) . . ? C13 C14 C15 119.0(7) . . ? C13 C14 C18 123.2(7) . . ? C15 C14 C18 117.9(7) . . ? C14 C15 C10 121.6(7) . . ? C10 C16 P4 115.8(5) . . ? C12 C17 P5 117.6(5) . . ? C14 C18 P6 114.9(5) . . ? C19 C19 C20 126.9(11) 2_466 . ? C21 C20 C24 117.2(8) . . ? C21 C20 C19 120.6(8) . . ? C24 C20 C19 122.1(8) . . ? C20 C21 C22 119.9(8) . . ? N1 C22 C21 119.7(8) . . ? N1 C23 C24 120.8(8) . . ? C23 C24 C20 120.4(8) . . ? C25 C25 C26 126.3(12) 2_777 . ? C27 C26 C30 118.0(7) . . ? C27 C26 C25 124.5(8) . . ? C30 C26 C25 117.5(8) . . ? C28 C27 C26 122.1(8) . . ? N2 C28 C27 119.2(8) . . ? N2 C29 C30 119.8(8) . . ? C29 C30 C26 117.5(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O3W 0.85 2.03 2.745(9) 141.8 . O3W H6W O6W 0.85 1.99 2.778(12) 154.4 . N1 H0A O11 0.96 1.83 2.778(8) 168.4 . N2 H0B O1 0.96 1.78 2.702(9) 159.2 . O1W H2W O5 0.85 1.91 2.723(7) 158.4 1_544 O2W H3W O4W 0.85 1.98 2.716(8) 143.8 2_566 O2W H4W O14 0.85 1.96 2.775(8) 160.8 1_655 O2 H2B O7 0.82 1.64 2.449(8) 170.8 2_667 O4 H4B O11 0.82 1.83 2.596(7) 155.8 2_567 O6W H11W O2 0.85 2.36 2.884(11) 120.8 1_454 O8 H8C O5 0.82 1.73 2.545(7) 174.6 2_677 O10 H10A O16 0.82 1.69 2.499(8) 168.9 2_556 O13 H13B O1 0.82 1.71 2.520(8) 170.6 2_667 O17 H17C O14 0.82 1.73 2.540(8) 170.1 2_566 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.254 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.156 data_2 _database_code_depnum_ccdc_archive 'CCDC 900075' #TrackingRef '2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H24 Ni1.50 O12 P3' _chemical_formula_weight 541.29 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' 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' Ni Ni 0.3393 1.1124 '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 8.0321(15) _cell_length_b 10.1400(19) _cell_length_c 12.985(2) _cell_angle_alpha 67.540(2) _cell_angle_beta 85.067(2) _cell_angle_gamma 74.216(2) _cell_volume 940.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6718 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 1.835 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.832 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6718 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3286 _reflns_number_gt 2780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0529P)^2^+0.9156P] 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 3286 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Ni1 Ni -1.0000 1.5000 0.5000 0.01384(17) Uani 1 2 d S . . Ni2 Ni -0.46701(6) 0.63338(5) 0.39319(4) 0.01394(14) Uani 1 1 d . . . O1W O -0.3721(3) 0.8117(3) 0.3703(2) 0.0221(6) Uani 1 1 d . . . H1W H -0.3962 0.8733 0.3039 0.027 Uiso 1 1 d R . . H2W H -0.2629 0.7906 0.3783 0.027 Uiso 1 1 d R . . O1 O -0.3843(3) 1.1327(3) -0.0586(2) 0.0254(6) Uani 1 1 d . . . O2W O -0.2079(3) 0.4838(3) 0.4200(2) 0.0181(6) Uani 1 1 d . . . H3W H -0.1899 0.4527 0.3668 0.022 Uiso 1 1 d R . . H4W H -0.2199 0.4015 0.4670 0.022 Uiso 1 1 d R . . O2 O -0.6489(4) 1.0988(3) -0.1271(2) 0.0275(7) Uani 1 1 d . . . H2A H -0.6377 1.0267 -0.0685 0.041 Uiso 1 1 calc R . . O3 O -0.5532(4) 1.3283(3) -0.2294(2) 0.0252(6) Uani 1 1 d . . . O3W O -0.0605(6) 0.4324(7) 0.2434(4) 0.132(3) Uani 1 1 d . . . H5W H -0.0448 0.4511 0.1742 0.158 Uiso 1 1 d R . . H6W H 0.0122 0.3485 0.2604 0.158 Uiso 1 1 d R . . O4 O -1.0202(3) 0.7094(3) 0.3773(2) 0.0195(6) Uani 1 1 d . . . O5 O -0.8631(4) 0.7883(3) 0.2005(2) 0.0253(6) Uani 1 1 d . . . H5A H -0.7787 0.8185 0.1721 0.038 Uiso 1 1 calc R . . O6 O -0.7228(3) 0.7447(3) 0.3855(2) 0.0193(6) Uani 1 1 d . . . O7 O -0.8257(3) 1.3921(3) 0.4139(2) 0.0215(6) Uani 1 1 d . . . O8 O -0.5334(3) 1.4317(3) 0.4349(2) 0.0164(5) Uani 1 1 d . . . O9 O -0.6596(4) 1.4994(3) 0.2444(2) 0.0255(6) Uani 1 1 d . . . H9C H -0.5970 1.5546 0.2353 0.038 Uiso 1 1 calc R . . P1 P -0.56036(13) 1.21214(11) -0.11458(8) 0.0205(2) Uani 1 1 d . . . P2 P -0.89052(12) 0.79659(10) 0.31916(8) 0.0148(2) Uani 1 1 d . . . P3 P -0.64803(12) 1.39192(10) 0.36870(8) 0.0147(2) Uani 1 1 d . . . C1 C -0.7118(5) 1.2266(4) 0.0903(3) 0.0193(8) Uani 1 1 d . . . C2 C -0.8440(5) 1.1528(4) 0.1298(3) 0.0193(8) Uani 1 1 d . . . C3 C -0.8610(5) 1.0850(4) 0.2452(3) 0.0169(8) Uani 1 1 d . . . C4 C -0.7632(5) 1.1062(4) 0.3195(3) 0.0169(8) Uani 1 1 d . . . C5 C -0.6341(4) 1.1824(4) 0.2793(3) 0.0161(8) Uani 1 1 d . . . C6 C -0.6006(5) 1.2337(4) 0.1649(3) 0.0185(8) Uani 1 1 d . . . C7 C -0.6973(5) 1.3088(4) -0.0345(3) 0.0229(9) Uani 1 1 d . . . H7A H -0.6569 1.3947 -0.0444 0.027 Uiso 1 1 calc R . . H7B H -0.8130 1.3450 -0.0671 0.027 Uiso 1 1 calc R . . C8 C -0.9673(5) 1.1520(5) 0.0487(3) 0.0277(10) Uani 1 1 d . . . H8A H -0.9347 1.2017 -0.0262 0.042 Uiso 1 1 calc R . . H8B H -1.0828 1.2020 0.0607 0.042 Uiso 1 1 calc R . . H8C H -0.9628 1.0518 0.0601 0.042 Uiso 1 1 calc R . . C9 C -0.9882(5) 0.9898(4) 0.2919(3) 0.0170(8) Uani 1 1 d . . . H9A H -1.0840 1.0252 0.2393 0.020 Uiso 1 1 calc R . . H9B H -1.0344 1.0005 0.3607 0.020 Uiso 1 1 calc R . . C10 C -0.8031(5) 1.0511(5) 0.4423(3) 0.0246(9) Uani 1 1 d . . . H10A H -0.7259 1.0732 0.4821 0.037 Uiso 1 1 calc R . . H10B H -0.7883 0.9461 0.4699 0.037 Uiso 1 1 calc R . . H10C H -0.9204 1.0989 0.4529 0.037 Uiso 1 1 calc R . . C11 C -0.5398(5) 1.2165(4) 0.3594(3) 0.0178(8) Uani 1 1 d . . . H11A H -0.4227 1.2174 0.3342 0.021 Uiso 1 1 calc R . . H11B H -0.5328 1.1391 0.4328 0.021 Uiso 1 1 calc R . . C12 C -0.4499(6) 1.3017(5) 0.1215(4) 0.0322(11) Uani 1 1 d . . . H12A H -0.3876 1.2975 0.1830 0.048 Uiso 1 1 calc R . . H12B H -0.4926 1.4028 0.0725 0.048 Uiso 1 1 calc R . . H12C H -0.3740 1.2478 0.0815 0.048 Uiso 1 1 calc R . . 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 Ni1 0.0122(3) 0.0154(3) 0.0156(4) -0.0060(3) 0.0030(3) -0.0068(3) Ni2 0.0146(3) 0.0170(3) 0.0120(3) -0.0050(2) 0.00196(18) -0.00813(19) O1W 0.0194(14) 0.0218(14) 0.0244(15) -0.0045(12) -0.0036(11) -0.0090(12) O1 0.0201(14) 0.0282(16) 0.0212(15) -0.0036(12) 0.0021(11) -0.0043(12) O2W 0.0182(13) 0.0194(13) 0.0193(14) -0.0069(11) 0.0005(11) -0.0096(11) O2 0.0363(17) 0.0261(15) 0.0194(15) -0.0041(12) 0.0013(12) -0.0137(13) O3 0.0340(16) 0.0263(15) 0.0123(14) -0.0030(12) 0.0071(12) -0.0115(13) O3W 0.097(4) 0.196(6) 0.078(3) -0.096(4) -0.049(3) 0.082(4) O4 0.0143(13) 0.0168(14) 0.0243(14) -0.0014(11) 0.0008(11) -0.0086(11) O5 0.0290(16) 0.0308(16) 0.0211(15) -0.0122(13) 0.0073(12) -0.0143(13) O6 0.0129(13) 0.0225(14) 0.0225(14) -0.0073(12) 0.0004(11) -0.0061(11) O7 0.0150(13) 0.0290(15) 0.0291(15) -0.0183(13) 0.0053(11) -0.0100(12) O8 0.0196(14) 0.0203(14) 0.0135(13) -0.0078(11) 0.0017(10) -0.0101(11) O9 0.0400(17) 0.0235(15) 0.0160(14) -0.0055(12) 0.0009(12) -0.0158(13) P1 0.0239(5) 0.0231(5) 0.0140(5) -0.0048(4) 0.0053(4) -0.0096(4) P2 0.0139(5) 0.0155(5) 0.0152(5) -0.0044(4) 0.0023(4) -0.0065(4) P3 0.0156(5) 0.0170(5) 0.0149(5) -0.0078(4) 0.0013(4) -0.0073(4) C1 0.023(2) 0.0184(19) 0.017(2) -0.0068(16) 0.0059(16) -0.0072(16) C2 0.022(2) 0.018(2) 0.020(2) -0.0095(17) 0.0013(16) -0.0054(16) C3 0.0190(19) 0.0121(18) 0.020(2) -0.0051(16) 0.0043(15) -0.0063(15) C4 0.022(2) 0.0139(18) 0.0146(19) -0.0050(15) 0.0030(15) -0.0056(15) C5 0.0147(18) 0.0143(18) 0.022(2) -0.0113(16) 0.0017(15) -0.0029(15) C6 0.019(2) 0.021(2) 0.020(2) -0.0114(17) 0.0073(15) -0.0099(16) C7 0.027(2) 0.022(2) 0.018(2) -0.0056(17) 0.0068(16) -0.0090(17) C8 0.026(2) 0.039(3) 0.020(2) -0.0082(19) 0.0026(17) -0.017(2) C9 0.0145(18) 0.0195(19) 0.0187(19) -0.0075(16) 0.0028(15) -0.0073(15) C10 0.034(2) 0.028(2) 0.016(2) -0.0058(17) 0.0027(17) -0.0179(19) C11 0.0174(19) 0.0172(19) 0.021(2) -0.0084(16) 0.0022(15) -0.0064(15) C12 0.039(3) 0.048(3) 0.025(2) -0.021(2) 0.020(2) -0.031(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 Ni1 O7 2.059(3) 2_386 ? Ni1 O7 2.059(3) . ? Ni1 O4 2.085(2) 2_376 ? Ni1 O4 2.085(2) 1_565 ? Ni1 O2W 2.115(2) 2_476 ? Ni1 O2W 2.115(2) 1_465 ? Ni2 O3 2.011(3) 2_475 ? Ni2 O6 2.048(3) . ? Ni2 O1W 2.059(3) . ? Ni2 O8 2.073(2) 2_476 ? Ni2 O8 2.112(2) 1_545 ? Ni2 O2W 2.181(3) . ? O1W H1W 0.8501 . ? O1W H2W 0.8499 . ? O1 P1 1.512(3) . ? O2W Ni1 2.115(2) 1_645 ? O2W H3W 0.8500 . ? O2W H4W 0.8500 . ? O2 P1 1.569(3) . ? O2 H2A 0.8200 . ? O3 P1 1.515(3) . ? O3 Ni2 2.011(3) 2_475 ? O3W H5W 0.8500 . ? O3W H6W 0.8500 . ? O4 P2 1.514(2) . ? O4 Ni1 2.085(2) 1_545 ? O5 P2 1.568(3) . ? O5 H5A 0.8200 . ? O6 P2 1.517(3) . ? O7 P3 1.495(3) . ? O8 P3 1.533(3) . ? O8 Ni2 2.073(2) 2_476 ? O8 Ni2 2.112(2) 1_565 ? O9 P3 1.558(3) . ? O9 H9C 0.8200 . ? P1 C7 1.802(4) . ? P2 C9 1.806(4) . ? P3 C11 1.800(4) . ? C1 C6 1.406(5) . ? C1 C2 1.413(5) . ? C1 C7 1.525(5) . ? C2 C3 1.402(5) . ? C2 C8 1.509(5) . ? C3 C4 1.406(5) . ? C3 C9 1.525(5) . ? C4 C5 1.407(5) . ? C4 C10 1.513(5) . ? C5 C6 1.403(5) . ? C5 C11 1.525(5) . ? C6 C12 1.516(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 O7 Ni1 O7 180.000(2) 2_386 . ? O7 Ni1 O4 94.40(10) 2_386 2_376 ? O7 Ni1 O4 85.60(10) . 2_376 ? O7 Ni1 O4 85.60(10) 2_386 1_565 ? O7 Ni1 O4 94.40(10) . 1_565 ? O4 Ni1 O4 180.00(14) 2_376 1_565 ? O7 Ni1 O2W 90.27(10) 2_386 2_476 ? O7 Ni1 O2W 89.73(10) . 2_476 ? O4 Ni1 O2W 88.45(10) 2_376 2_476 ? O4 Ni1 O2W 91.55(10) 1_565 2_476 ? O7 Ni1 O2W 89.73(10) 2_386 1_465 ? O7 Ni1 O2W 90.27(10) . 1_465 ? O4 Ni1 O2W 91.55(10) 2_376 1_465 ? O4 Ni1 O2W 88.45(10) 1_565 1_465 ? O2W Ni1 O2W 180.000(1) 2_476 1_465 ? O3 Ni2 O6 95.68(11) 2_475 . ? O3 Ni2 O1W 90.55(11) 2_475 . ? O6 Ni2 O1W 95.76(10) . . ? O3 Ni2 O8 172.83(10) 2_475 2_476 ? O6 Ni2 O8 90.15(10) . 2_476 ? O1W Ni2 O8 93.02(10) . 2_476 ? O3 Ni2 O8 94.46(10) 2_475 1_545 ? O6 Ni2 O8 90.90(10) . 1_545 ? O1W Ni2 O8 171.24(10) . 1_545 ? O8 Ni2 O8 81.25(10) 2_476 1_545 ? O3 Ni2 O2W 89.08(10) 2_475 . ? O6 Ni2 O2W 170.72(10) . . ? O1W Ni2 O2W 92.15(10) . . ? O8 Ni2 O2W 84.57(10) 2_476 . ? O8 Ni2 O2W 80.77(9) 1_545 . ? Ni2 O1W H1W 108.5 . . ? Ni2 O1W H2W 114.3 . . ? H1W O1W H2W 106.4 . . ? Ni1 O2W Ni2 125.01(12) 1_645 . ? Ni1 O2W H3W 120.8 1_645 . ? Ni2 O2W H3W 107.0 . . ? Ni1 O2W H4W 98.3 1_645 . ? Ni2 O2W H4W 105.2 . . ? H3W O2W H4W 93.0 . . ? P1 O2 H2A 109.5 . . ? P1 O3 Ni2 144.68(18) . 2_475 ? H5W O3W H6W 91.6 . . ? P2 O4 Ni1 133.97(15) . 1_545 ? P2 O5 H5A 109.5 . . ? P2 O6 Ni2 143.96(17) . . ? P3 O7 Ni1 137.45(16) . . ? P3 O8 Ni2 124.40(14) . 2_476 ? P3 O8 Ni2 128.29(15) . 1_565 ? Ni2 O8 Ni2 98.75(10) 2_476 1_565 ? P3 O9 H9C 109.5 . . ? O1 P1 O3 113.19(16) . . ? O1 P1 O2 110.13(16) . . ? O3 P1 O2 107.83(16) . . ? O1 P1 C7 110.68(18) . . ? O3 P1 C7 105.71(17) . . ? O2 P1 C7 109.12(17) . . ? O4 P2 O6 112.93(14) . . ? O4 P2 O5 107.14(15) . . ? O6 P2 O5 112.98(15) . . ? O4 P2 C9 108.84(16) . . ? O6 P2 C9 110.17(16) . . ? O5 P2 C9 104.35(16) . . ? O7 P3 O8 114.02(15) . . ? O7 P3 O9 110.03(16) . . ? O8 P3 O9 109.45(15) . . ? O7 P3 C11 110.98(16) . . ? O8 P3 C11 109.45(16) . . ? O9 P3 C11 102.26(17) . . ? C6 C1 C2 120.9(3) . . ? C6 C1 C7 119.4(3) . . ? C2 C1 C7 119.6(3) . . ? C3 C2 C1 118.6(3) . . ? C3 C2 C8 121.1(3) . . ? C1 C2 C8 120.2(3) . . ? C2 C3 C4 120.3(3) . . ? C2 C3 C9 120.6(3) . . ? C4 C3 C9 119.0(3) . . ? C3 C4 C5 120.3(3) . . ? C3 C4 C10 119.1(3) . . ? C5 C4 C10 120.6(3) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 C11 120.7(3) . . ? C4 C5 C11 119.7(3) . . ? C5 C6 C1 119.4(3) . . ? C5 C6 C12 120.3(3) . . ? C1 C6 C12 120.3(3) . . ? C1 C7 P1 118.9(3) . . ? C1 C7 H7A 107.6 . . ? P1 C7 H7A 107.6 . . ? C1 C7 H7B 107.6 . . ? P1 C7 H7B 107.6 . . ? H7A C7 H7B 107.0 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 P2 112.8(3) . . ? C3 C9 H9A 109.0 . . ? P2 C9 H9A 109.0 . . ? C3 C9 H9B 109.0 . . ? P2 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 P3 111.8(3) . . ? C5 C11 H11A 109.3 . . ? P3 C11 H11A 109.3 . . ? C5 C11 H11B 109.3 . . ? P3 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2W H3W O3W 0.85 1.88 2.654(5) 150.4 . O1W H1W O2 0.85 2.21 2.937(4) 143.0 2_475 O2 H2A O1 0.82 1.80 2.615(4) 178.8 2_475 O5 H5A O1 0.82 1.90 2.663(4) 155.3 2_475 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.917 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.098 data_3 _database_code_depnum_ccdc_archive 'CCDC 900076' #TrackingRef '3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H31 N2 Ni O11 P3' _chemical_formula_weight 675.13 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' Ni Ni 0.3393 1.1124 '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 9.981(4) _cell_length_b 10.454(4) _cell_length_c 13.701(6) _cell_angle_alpha 86.396(4) _cell_angle_beta 71.039(4) _cell_angle_gamma 82.803(4) _cell_volume 1341.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7640 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7640 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4644 _reflns_number_gt 3973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0368P)^2^+1.1417P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4644 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.86052(3) 0.26351(3) 0.35730(2) 0.01982(10) Uani 1 1 d . . . O1W O 0.8889(2) 0.10945(17) 0.45943(14) 0.0293(4) Uani 1 1 d . . . H1W H 0.8990 0.1166 0.5180 0.035 Uiso 1 1 d R . . H2W H 0.9585 0.0633 0.4189 0.035 Uiso 1 1 d R . . O1 O 1.02781(19) 0.64633(17) -0.06861(13) 0.0255(4) Uani 1 1 d . . . O2W O 0.9172(2) 0.3954(2) 0.43794(16) 0.0283(4) Uani 1 1 d . . . H3W H 0.942(4) 0.462(4) 0.410(3) 0.050(11) Uiso 1 1 d . . . H4W H 0.958(3) 0.379(3) 0.483(3) 0.041(10) Uiso 1 1 d . . . O2 O 1.09702(19) 0.41589(16) -0.12506(13) 0.0258(4) Uani 1 1 d . . . H2A H 1.0590 0.4046 -0.0629 0.039 Uiso 1 1 calc R . . O3 O 1.1622(2) 0.58804(17) -0.25898(13) 0.0280(4) Uani 1 1 d . . . O4 O 1.13192(19) 0.15057(18) 0.08859(14) 0.0299(4) Uani 1 1 d . . . H4A H 1.0810 0.2178 0.0860 0.045 Uiso 1 1 calc R . . O5 O 1.2255(2) 0.00543(17) 0.20752(15) 0.0325(5) Uani 1 1 d . . . H5A H 1.1624 -0.0233 0.2555 0.049 Uiso 1 1 calc R . . O6 O 1.06832(19) 0.21257(18) 0.27504(14) 0.0293(4) Uani 1 1 d . . . O7 O 1.0594(2) 0.87683(17) 0.35194(13) 0.0281(4) Uani 1 1 d . . . O8 O 0.97265(19) 0.76699(18) 0.23329(14) 0.0294(4) Uani 1 1 d . . . H8D H 0.9662 0.6976 0.2113 0.044 Uiso 1 1 calc R . . O9 O 0.9984(2) 0.64587(17) 0.39344(13) 0.0288(4) Uani 1 1 d . . . N1 N 0.7615(2) 0.1343(2) 0.29479(16) 0.0246(5) Uani 1 1 d . . . N2 N 0.6511(2) 0.2930(2) 0.45526(16) 0.0237(5) Uani 1 1 d . . . P1 P 1.13906(7) 0.55923(6) -0.14702(5) 0.02066(15) Uani 1 1 d . . . P2 P 1.05934(7) 0.74362(6) 0.31223(5) 0.02070(15) Uani 1 1 d . . . P3 P 1.17954(7) 0.14889(6) 0.18642(5) 0.02243(16) Uani 1 1 d . . . C1 C 1.3066(2) 0.5239(2) -0.01516(18) 0.0204(5) Uani 1 1 d . . . C2 C 1.3351(3) 0.3941(2) 0.01227(19) 0.0212(5) Uani 1 1 d . . . C3 C 1.3243(2) 0.3615(2) 0.11516(19) 0.0203(5) Uani 1 1 d . . . C4 C 1.2903(3) 0.4575(2) 0.18945(18) 0.0200(5) Uani 1 1 d . . . C5 C 1.2690(3) 0.5871(2) 0.15995(18) 0.0191(5) Uani 1 1 d . . . C6 C 1.2749(3) 0.6208(2) 0.05749(19) 0.0202(5) Uani 1 1 d . . . C7 C 1.3089(3) 0.5587(3) -0.12527(19) 0.0229(5) Uani 1 1 d . . . H7A H 1.3783 0.4979 -0.1715 0.027 Uiso 1 1 calc R . . H7B H 1.3407 0.6436 -0.1432 0.027 Uiso 1 1 calc R . . C8 C 1.3820(3) 0.2918(3) -0.0694(2) 0.0275(6) Uani 1 1 d . . . H8A H 1.3972 0.2090 -0.0379 0.041 Uiso 1 1 calc R . . H8B H 1.4690 0.3112 -0.1209 0.041 Uiso 1 1 calc R . . H8C H 1.3094 0.2905 -0.1010 0.041 Uiso 1 1 calc R . . C9 C 1.3437(3) 0.2212(2) 0.1493(2) 0.0232(5) Uani 1 1 d . . . H9A H 1.3800 0.2159 0.2072 0.028 Uiso 1 1 calc R . . H9B H 1.4136 0.1732 0.0932 0.028 Uiso 1 1 calc R . . C10 C 1.2825(3) 0.4202(3) 0.29981(19) 0.0282(6) Uani 1 1 d . . . H10A H 1.2584 0.4963 0.3405 0.042 Uiso 1 1 calc R . . H10B H 1.3732 0.3782 0.3009 0.042 Uiso 1 1 calc R . . H10C H 1.2109 0.3626 0.3279 0.042 Uiso 1 1 calc R . . C11 C 1.2428(3) 0.6931(2) 0.23727(19) 0.0221(5) Uani 1 1 d . . . H11A H 1.2841 0.7682 0.2000 0.026 Uiso 1 1 calc R . . H11B H 1.2945 0.6644 0.2851 0.026 Uiso 1 1 calc R . . C12 C 1.2514(3) 0.7611(2) 0.0248(2) 0.0284(6) Uani 1 1 d . . . H12A H 1.2592 0.7662 -0.0470 0.043 Uiso 1 1 calc R . . H12B H 1.3219 0.8079 0.0357 0.043 Uiso 1 1 calc R . . H12C H 1.1581 0.7978 0.0650 0.043 Uiso 1 1 calc R . . C13 C 0.8139(3) 0.0576(3) 0.2150(2) 0.0321(6) Uani 1 1 d . . . H13A H 0.9098 0.0577 0.1767 0.038 Uiso 1 1 calc R . . C14 C 0.7343(3) -0.0235(3) 0.1847(2) 0.0381(7) Uani 1 1 d . . . H14A H 0.7758 -0.0738 0.1266 0.046 Uiso 1 1 calc R . . C15 C 0.5950(3) -0.0275(3) 0.2417(2) 0.0375(7) Uani 1 1 d . . . H15A H 0.5405 -0.0818 0.2233 0.045 Uiso 1 1 calc R . . C16 C 0.5336(3) 0.0503(3) 0.3282(2) 0.0297(6) Uani 1 1 d . . . C17 C 0.3880(3) 0.0508(3) 0.3937(2) 0.0397(7) Uani 1 1 d . . . H17A H 0.3304 -0.0045 0.3802 0.048 Uiso 1 1 calc R . . C18 C 0.3338(3) 0.1303(3) 0.4744(2) 0.0406(7) Uani 1 1 d . . . H18A H 0.2390 0.1295 0.5151 0.049 Uiso 1 1 calc R . . C19 C 0.4192(3) 0.2159(3) 0.4987(2) 0.0320(6) Uani 1 1 d . . . C20 C 0.3682(3) 0.3010(3) 0.5812(2) 0.0429(8) Uani 1 1 d . . . H20A H 0.2737 0.3047 0.6235 0.051 Uiso 1 1 calc R . . C21 C 0.4578(3) 0.3781(3) 0.5991(2) 0.0414(8) Uani 1 1 d . . . H21A H 0.4252 0.4349 0.6536 0.050 Uiso 1 1 calc R . . C22 C 0.5991(3) 0.3706(3) 0.5346(2) 0.0313(6) Uani 1 1 d . . . H22A H 0.6597 0.4228 0.5480 0.038 Uiso 1 1 calc R . . C23 C 0.5625(3) 0.2152(2) 0.43695(19) 0.0245(6) Uani 1 1 d . . . C24 C 0.6209(3) 0.1318(2) 0.3512(2) 0.0233(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02148(18) 0.02115(18) 0.01751(17) -0.00135(13) -0.00625(13) -0.00442(13) O1W 0.0372(11) 0.0262(10) 0.0242(10) 0.0008(8) -0.0107(8) -0.0002(8) O1 0.0276(10) 0.0278(10) 0.0190(9) 0.0001(7) -0.0056(8) -0.0006(8) O2W 0.0420(12) 0.0242(11) 0.0249(10) 0.0022(9) -0.0166(9) -0.0122(9) O2 0.0330(10) 0.0259(10) 0.0201(9) 0.0004(7) -0.0086(8) -0.0088(8) O3 0.0373(11) 0.0287(10) 0.0178(9) 0.0024(8) -0.0097(8) -0.0029(8) O4 0.0298(10) 0.0290(10) 0.0324(10) -0.0047(8) -0.0118(8) -0.0024(8) O5 0.0335(11) 0.0196(10) 0.0396(11) 0.0025(8) -0.0054(9) -0.0041(8) O6 0.0222(9) 0.0311(10) 0.0316(10) -0.0054(8) -0.0036(8) -0.0032(8) O7 0.0391(11) 0.0203(9) 0.0238(9) -0.0040(7) -0.0071(8) -0.0054(8) O8 0.0356(11) 0.0281(10) 0.0288(10) -0.0016(8) -0.0165(9) -0.0018(8) O9 0.0382(11) 0.0256(10) 0.0238(9) 0.0035(8) -0.0097(8) -0.0109(8) N1 0.0261(12) 0.0251(12) 0.0232(11) -0.0007(9) -0.0085(9) -0.0035(9) N2 0.0247(11) 0.0261(12) 0.0194(11) -0.0001(9) -0.0063(9) -0.0019(9) P1 0.0241(3) 0.0228(3) 0.0159(3) 0.0002(3) -0.0071(3) -0.0040(3) P2 0.0274(4) 0.0176(3) 0.0183(3) -0.0007(3) -0.0081(3) -0.0045(3) P3 0.0218(3) 0.0182(3) 0.0261(3) -0.0013(3) -0.0056(3) -0.0032(3) C1 0.0172(12) 0.0257(13) 0.0193(12) 0.0014(10) -0.0061(10) -0.0066(10) C2 0.0178(12) 0.0226(13) 0.0230(13) -0.0037(10) -0.0051(10) -0.0039(10) C3 0.0165(12) 0.0202(13) 0.0256(13) 0.0001(10) -0.0074(10) -0.0057(10) C4 0.0205(12) 0.0202(13) 0.0208(12) 0.0005(10) -0.0077(10) -0.0060(10) C5 0.0198(12) 0.0196(13) 0.0186(12) -0.0016(10) -0.0060(10) -0.0044(10) C6 0.0202(12) 0.0203(13) 0.0209(12) -0.0003(10) -0.0066(10) -0.0050(10) C7 0.0241(13) 0.0247(13) 0.0196(13) -0.0020(10) -0.0053(11) -0.0058(11) C8 0.0277(14) 0.0285(14) 0.0253(14) -0.0071(11) -0.0069(11) 0.0000(11) C9 0.0196(13) 0.0203(13) 0.0294(14) -0.0022(11) -0.0073(11) -0.0013(10) C10 0.0380(16) 0.0253(14) 0.0233(14) -0.0002(11) -0.0126(12) -0.0045(12) C11 0.0248(13) 0.0199(13) 0.0233(13) -0.0019(10) -0.0097(11) -0.0029(10) C12 0.0384(16) 0.0226(14) 0.0254(14) 0.0027(11) -0.0116(12) -0.0055(12) C13 0.0292(15) 0.0343(16) 0.0322(15) -0.0080(13) -0.0077(12) -0.0043(12) C14 0.0421(18) 0.0354(17) 0.0396(17) -0.0149(14) -0.0138(14) -0.0055(14) C15 0.0413(18) 0.0336(16) 0.0457(18) -0.0043(14) -0.0216(15) -0.0116(13) C16 0.0303(15) 0.0274(14) 0.0363(15) 0.0039(12) -0.0171(13) -0.0067(12) C17 0.0314(16) 0.0436(18) 0.0500(19) 0.0057(15) -0.0179(15) -0.0166(14) C18 0.0244(15) 0.053(2) 0.0426(18) 0.0025(15) -0.0064(13) -0.0114(14) C19 0.0244(14) 0.0400(16) 0.0281(14) 0.0051(12) -0.0052(12) -0.0028(12) C20 0.0272(16) 0.059(2) 0.0335(16) -0.0014(15) 0.0015(13) -0.0006(15) C21 0.0390(18) 0.051(2) 0.0279(16) -0.0112(14) -0.0029(14) 0.0017(15) C22 0.0344(16) 0.0351(16) 0.0241(14) -0.0057(12) -0.0085(12) -0.0024(12) C23 0.0249(14) 0.0264(14) 0.0225(13) 0.0051(11) -0.0089(11) -0.0035(11) C24 0.0238(13) 0.0226(13) 0.0260(13) 0.0048(11) -0.0115(11) -0.0043(10) _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 Ni1 O3 2.0302(18) 2_765 ? Ni1 O6 2.0336(19) . ? Ni1 O2W 2.058(2) . ? Ni1 N2 2.081(2) . ? Ni1 O1W 2.1194(18) . ? Ni1 N1 2.136(2) . ? O1 P1 1.5201(18) . ? O2 P1 1.5909(19) . ? O3 P1 1.4922(18) . ? O3 Ni1 2.0302(18) 2_765 ? O4 P3 1.559(2) . ? O5 P3 1.5501(19) . ? O6 P3 1.4799(19) . ? O7 P2 1.5268(19) . ? O8 P2 1.5811(19) . ? O9 P2 1.4917(19) . ? N1 C13 1.321(3) . ? N1 C24 1.367(3) . ? N2 C22 1.322(3) . ? N2 C23 1.362(3) . ? P1 C7 1.813(3) . ? P2 C11 1.814(3) . ? P3 C9 1.799(3) . ? C1 C6 1.400(3) . ? C1 C2 1.404(3) . ? C1 C7 1.523(3) . ? C2 C3 1.402(3) . ? C2 C8 1.516(3) . ? C3 C4 1.406(3) . ? C3 C9 1.520(3) . ? C4 C5 1.400(3) . ? C4 C10 1.517(3) . ? C5 C6 1.410(3) . ? C5 C11 1.522(3) . ? C6 C12 1.519(3) . ? C13 C14 1.398(4) . ? C14 C15 1.360(4) . ? C15 C16 1.403(4) . ? C16 C24 1.408(4) . ? C16 C17 1.438(4) . ? C17 C18 1.349(4) . ? C18 C19 1.432(4) . ? C19 C20 1.403(4) . ? C19 C23 1.405(4) . ? C20 C21 1.363(5) . ? C21 C22 1.396(4) . ? C23 C24 1.427(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Ni1 O6 93.46(8) 2_765 . ? O3 Ni1 O2W 86.48(9) 2_765 . ? O6 Ni1 O2W 91.12(8) . . ? O3 Ni1 N2 94.76(8) 2_765 . ? O6 Ni1 N2 171.77(8) . . ? O2W Ni1 N2 89.74(9) . . ? O3 Ni1 O1W 178.72(8) 2_765 . ? O6 Ni1 O1W 85.52(8) . . ? O2W Ni1 O1W 92.78(9) . . ? N2 Ni1 O1W 86.27(8) . . ? O3 Ni1 N1 94.58(8) 2_765 . ? O6 Ni1 N1 99.82(8) . . ? O2W Ni1 N1 168.91(8) . . ? N2 Ni1 N1 79.17(9) . . ? O1W Ni1 N1 86.35(8) . . ? P1 O3 Ni1 141.02(12) . 2_765 ? P3 O6 Ni1 151.36(12) . . ? C13 N1 C24 117.2(2) . . ? C13 N1 Ni1 131.08(19) . . ? C24 N1 Ni1 111.69(17) . . ? C22 N2 C23 118.1(2) . . ? C22 N2 Ni1 127.79(19) . . ? C23 N2 Ni1 113.95(17) . . ? O3 P1 O1 118.39(10) . . ? O3 P1 O2 106.81(10) . . ? O1 P1 O2 108.16(10) . . ? O3 P1 C7 107.66(11) . . ? O1 P1 C7 108.45(11) . . ? O2 P1 C7 106.82(11) . . ? O9 P2 O7 115.19(11) . . ? O9 P2 O8 111.04(11) . . ? O7 P2 O8 105.36(10) . . ? O9 P2 C11 112.09(12) . . ? O7 P2 C11 105.87(11) . . ? O8 P2 C11 106.70(11) . . ? O6 P3 O5 114.07(11) . . ? O6 P3 O4 112.66(11) . . ? O5 P3 O4 105.83(11) . . ? O6 P3 C9 112.90(12) . . ? O5 P3 C9 103.55(11) . . ? O4 P3 C9 107.10(12) . . ? C6 C1 C2 120.9(2) . . ? C6 C1 C7 119.9(2) . . ? C2 C1 C7 119.3(2) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 C8 120.7(2) . . ? C1 C2 C8 120.2(2) . . ? C2 C3 C4 120.7(2) . . ? C2 C3 C9 120.5(2) . . ? C4 C3 C9 118.7(2) . . ? C5 C4 C3 119.6(2) . . ? C5 C4 C10 120.6(2) . . ? C3 C4 C10 119.8(2) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 C11 120.4(2) . . ? C6 C5 C11 119.3(2) . . ? C1 C6 C5 119.4(2) . . ? C1 C6 C12 119.9(2) . . ? C5 C6 C12 120.6(2) . . ? C1 C7 P1 114.76(17) . . ? C3 C9 P3 112.04(17) . . ? C5 C11 P2 117.36(18) . . ? N1 C13 C14 124.1(3) . . ? C15 C14 C13 118.7(3) . . ? C14 C15 C16 119.9(3) . . ? C15 C16 C24 117.4(3) . . ? C15 C16 C17 123.7(3) . . ? C24 C16 C17 118.9(3) . . ? C18 C17 C16 121.0(3) . . ? C17 C18 C19 121.3(3) . . ? C20 C19 C23 117.6(3) . . ? C20 C19 C18 123.7(3) . . ? C23 C19 C18 118.7(3) . . ? C21 C20 C19 119.7(3) . . ? C20 C21 C22 119.1(3) . . ? N2 C22 C21 123.2(3) . . ? N2 C23 C19 122.3(2) . . ? N2 C23 C24 117.2(2) . . ? C19 C23 C24 120.5(2) . . ? N1 C24 C16 122.6(2) . . ? N1 C24 C23 117.8(2) . . ? C16 C24 C23 119.6(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.442 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.060 data_4 _database_code_depnum_ccdc_archive 'CCDC 900077' #TrackingRef '4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 N2 Ni O11 P3' _chemical_formula_weight 651.11 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' Ni Ni 0.3393 1.1124 '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 9.9667(6) _cell_length_b 10.4207(6) _cell_length_c 13.3783(8) _cell_angle_alpha 94.0540(10) _cell_angle_beta 106.8400(10) _cell_angle_gamma 93.6490(10) _cell_volume 1321.40(14) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3066 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 26.21 _exptl_crystal_description Plate _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.979 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7459 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.21 _reflns_number_total 5227 _reflns_number_gt 4253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0412P)^2^+1.2213P] 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 5227 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Ni1 Ni 0.34442(4) 0.23373(4) 0.13780(3) 0.01471(11) Uani 1 1 d . . . O1W O 0.3570(2) 0.07990(19) 0.02882(17) 0.0211(5) Uani 1 1 d . . . H1W H 0.3999 0.0970 -0.0157 0.025 Uiso 1 1 d R . . H2W H 0.4006 0.0233 0.0650 0.025 Uiso 1 1 d R . . O1 O 0.5302(2) 0.6540(2) 0.56959(17) 0.0190(5) Uani 1 1 d . . . O2W O 0.3997(2) 0.37383(19) 0.05344(16) 0.0191(5) Uani 1 1 d . . . H3W H 0.4210 0.4486 0.0864 0.023 Uiso 1 1 d R . . H4W H 0.4356 0.3664 0.0031 0.023 Uiso 1 1 d R . . O2 O 0.5937(2) 0.43306(19) 0.62225(17) 0.0180(5) Uani 1 1 d . . . H2A H 0.5555 0.4157 0.5592 0.027 Uiso 1 1 calc R . . O3 O 0.6628(2) 0.6167(2) 0.75982(17) 0.0203(5) Uani 1 1 d . . . O4 O 0.4645(2) 0.7609(2) 0.26827(17) 0.0207(5) Uani 1 1 d . . . H4A H 0.4584 0.6905 0.2912 0.031 Uiso 1 1 calc R . . O5 O 0.4790(2) 0.6391(2) 0.10123(17) 0.0197(5) Uani 1 1 d . . . O6 O 0.5383(2) 0.88241(19) 0.13846(17) 0.0175(5) Uani 1 1 d . . . O7 O 0.7130(2) 0.0408(2) 0.27231(19) 0.0239(5) Uani 1 1 d . . . H7C H 0.6482 -0.0021 0.2281 0.036 Uiso 1 1 calc R . . O8 O 0.6221(2) 0.1678(2) 0.39902(17) 0.0216(5) Uani 1 1 d . . . H8D H 0.5739 0.2271 0.4049 0.032 Uiso 1 1 calc R . . O9 O 0.5523(2) 0.2162(2) 0.20915(17) 0.0202(5) Uani 1 1 d . . . N1 N 0.2468(3) 0.0937(2) 0.2072(2) 0.0185(6) Uani 1 1 d . . . N2 N 0.1327(3) 0.2433(2) 0.0600(2) 0.0188(6) Uani 1 1 d . . . P1 P 0.63871(9) 0.58338(7) 0.64556(6) 0.01581(18) Uani 1 1 d . . . P2 P 0.54239(8) 0.74992(7) 0.18122(6) 0.01462(18) Uani 1 1 d . . . P3 P 0.66595(8) 0.17523(7) 0.29661(7) 0.01668(18) Uani 1 1 d . . . C1 C 0.7985(3) 0.5750(3) 0.5051(2) 0.0158(6) Uani 1 1 d . . . C2 C 0.7667(3) 0.6673(3) 0.4314(2) 0.0169(6) Uani 1 1 d . . . C3 C 0.7538(3) 0.6318(3) 0.3262(2) 0.0142(6) Uani 1 1 d . . . C4 C 0.7718(3) 0.5054(3) 0.2927(2) 0.0162(6) Uani 1 1 d . . . C5 C 0.8083(3) 0.4150(3) 0.3675(2) 0.0151(6) Uani 1 1 d . . . C6 C 0.8222(3) 0.4488(3) 0.4729(2) 0.0152(6) Uani 1 1 d . . . C7 C 0.8053(3) 0.6095(3) 0.6179(2) 0.0182(7) Uani 1 1 d . . . H7A H 0.8397 0.6998 0.6367 0.022 Uiso 1 1 calc R . . H7B H 0.8728 0.5587 0.6620 0.022 Uiso 1 1 calc R . . C8 C 0.7508(4) 0.8050(3) 0.4686(3) 0.0226(7) Uani 1 1 d . . . H8A H 0.7285 0.8559 0.4098 0.034 Uiso 1 1 calc R . . H8B H 0.8373 0.8411 0.5186 0.034 Uiso 1 1 calc R . . H8C H 0.6764 0.8052 0.5009 0.034 Uiso 1 1 calc R . . C9 C 0.7257(3) 0.7340(3) 0.2480(2) 0.0155(6) Uani 1 1 d . . . H9A H 0.7729 0.7138 0.1955 0.019 Uiso 1 1 calc R . . H9B H 0.7679 0.8169 0.2849 0.019 Uiso 1 1 calc R . . C10 C 0.7593(3) 0.4662(3) 0.1793(2) 0.0195(7) Uani 1 1 d . . . H10A H 0.7334 0.5379 0.1386 0.029 Uiso 1 1 calc R . . H10B H 0.6886 0.3951 0.1532 0.029 Uiso 1 1 calc R . . H10C H 0.8481 0.4407 0.1740 0.029 Uiso 1 1 calc R . . C11 C 0.8270(3) 0.2785(3) 0.3298(2) 0.0170(6) Uani 1 1 d . . . H11A H 0.8978 0.2430 0.3843 0.020 Uiso 1 1 calc R . . H11B H 0.8605 0.2808 0.2687 0.020 Uiso 1 1 calc R . . C12 C 0.8687(3) 0.3537(3) 0.5542(2) 0.0186(7) Uani 1 1 d . . . H12A H 0.8735 0.3936 0.6222 0.028 Uiso 1 1 calc R . . H12B H 0.9599 0.3285 0.5546 0.028 Uiso 1 1 calc R . . H12C H 0.8023 0.2788 0.5373 0.028 Uiso 1 1 calc R . . C13 C 0.3102(4) 0.0199(3) 0.2817(3) 0.0229(7) Uani 1 1 d . . . H13A H 0.4080 0.0267 0.3055 0.027 Uiso 1 1 calc R . . C14 C 0.2365(4) -0.0662(3) 0.3249(3) 0.0310(9) Uani 1 1 d . . . H14A H 0.2838 -0.1159 0.3768 0.037 Uiso 1 1 calc R . . C15 C 0.0931(4) -0.0769(4) 0.2899(3) 0.0399(10) Uani 1 1 d . . . H15A H 0.0411 -0.1326 0.3188 0.048 Uiso 1 1 calc R . . C16 C 0.0258(4) -0.0038(4) 0.2108(3) 0.0349(9) Uani 1 1 d . . . H16A H -0.0718 -0.0120 0.1845 0.042 Uiso 1 1 calc R . . C17 C 0.1049(3) 0.0814(3) 0.1712(3) 0.0212(7) Uani 1 1 d . . . C18 C 0.0410(4) 0.1658(3) 0.0890(3) 0.0227(7) Uani 1 1 d . . . C19 C -0.1025(4) 0.1666(4) 0.0455(3) 0.0353(9) Uani 1 1 d . . . H19A H -0.1643 0.1114 0.0664 0.042 Uiso 1 1 calc R . . C20 C -0.1539(4) 0.2510(4) -0.0298(3) 0.0432(11) Uani 1 1 d . . . H20A H -0.2502 0.2538 -0.0597 0.052 Uiso 1 1 calc R . . C21 C -0.0589(4) 0.3303(4) -0.0589(3) 0.0378(10) Uani 1 1 d . . . H21A H -0.0901 0.3877 -0.1091 0.045 Uiso 1 1 calc R . . C22 C 0.0813(4) 0.3238(3) -0.0134(3) 0.0273(8) Uani 1 1 d . . . H22A H 0.1445 0.3775 -0.0341 0.033 Uiso 1 1 calc R . . 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 Ni1 0.0149(2) 0.0150(2) 0.0143(2) 0.00161(15) 0.00451(16) 0.00081(15) O1W 0.0260(13) 0.0163(11) 0.0241(13) 0.0019(9) 0.0118(10) 0.0028(9) O1 0.0195(12) 0.0199(11) 0.0175(12) 0.0014(9) 0.0048(9) 0.0030(9) O2W 0.0267(13) 0.0150(11) 0.0157(12) 0.0008(9) 0.0078(10) -0.0026(9) O2 0.0221(12) 0.0170(11) 0.0147(11) 0.0001(9) 0.0058(9) -0.0009(9) O3 0.0269(13) 0.0209(11) 0.0142(12) 0.0010(9) 0.0073(10) 0.0039(9) O4 0.0266(13) 0.0188(11) 0.0213(12) 0.0059(9) 0.0126(10) 0.0061(9) O5 0.0224(12) 0.0165(11) 0.0198(12) -0.0002(9) 0.0068(10) -0.0008(9) O6 0.0222(12) 0.0132(10) 0.0175(12) 0.0036(8) 0.0054(9) 0.0037(9) O7 0.0215(12) 0.0146(11) 0.0322(14) -0.0023(9) 0.0039(10) 0.0015(9) O8 0.0228(12) 0.0193(12) 0.0242(13) 0.0051(9) 0.0084(10) 0.0042(9) O9 0.0157(11) 0.0207(11) 0.0230(13) 0.0019(9) 0.0036(10) 0.0018(9) N1 0.0195(14) 0.0160(13) 0.0206(15) 0.0002(11) 0.0076(12) -0.0001(11) N2 0.0178(14) 0.0206(14) 0.0172(14) 0.0002(11) 0.0043(11) 0.0015(11) P1 0.0178(4) 0.0167(4) 0.0139(4) 0.0007(3) 0.0064(3) 0.0012(3) P2 0.0178(4) 0.0122(4) 0.0142(4) 0.0015(3) 0.0051(3) 0.0018(3) P3 0.0152(4) 0.0132(4) 0.0209(4) 0.0017(3) 0.0041(3) 0.0015(3) C1 0.0123(15) 0.0186(15) 0.0175(16) 0.0015(12) 0.0063(13) -0.0012(12) C2 0.0124(15) 0.0165(15) 0.0224(17) 0.0024(12) 0.0063(13) 0.0005(12) C3 0.0114(15) 0.0159(15) 0.0166(16) 0.0060(12) 0.0051(12) 0.0011(11) C4 0.0143(16) 0.0171(15) 0.0169(16) 0.0011(12) 0.0047(13) 0.0002(12) C5 0.0121(15) 0.0151(15) 0.0182(16) 0.0011(12) 0.0052(13) -0.0007(11) C6 0.0103(15) 0.0164(15) 0.0184(16) 0.0039(12) 0.0032(12) -0.0004(12) C7 0.0189(17) 0.0190(16) 0.0163(16) 0.0006(12) 0.0053(13) -0.0001(13) C8 0.0288(19) 0.0174(16) 0.0204(18) 0.0004(13) 0.0058(15) 0.0011(13) C9 0.0173(16) 0.0127(14) 0.0174(16) 0.0039(12) 0.0057(13) 0.0026(12) C10 0.0220(17) 0.0188(16) 0.0204(17) 0.0028(13) 0.0099(14) 0.0047(13) C11 0.0154(16) 0.0157(15) 0.0201(17) 0.0045(12) 0.0052(13) 0.0011(12) C12 0.0190(17) 0.0183(16) 0.0181(17) 0.0023(13) 0.0045(13) 0.0025(12) C13 0.0210(18) 0.0215(17) 0.0267(19) 0.0053(14) 0.0077(15) 0.0002(13) C14 0.034(2) 0.0259(19) 0.038(2) 0.0149(16) 0.0152(18) 0.0068(16) C15 0.034(2) 0.035(2) 0.059(3) 0.023(2) 0.023(2) -0.0004(17) C16 0.0193(19) 0.036(2) 0.052(3) 0.0135(19) 0.0137(18) 0.0000(16) C17 0.0193(17) 0.0180(16) 0.0274(19) 0.0008(13) 0.0091(14) -0.0005(13) C18 0.0230(18) 0.0216(17) 0.0225(18) -0.0019(13) 0.0066(14) 0.0000(13) C19 0.0191(19) 0.041(2) 0.043(2) 0.0089(18) 0.0056(17) -0.0042(16) C20 0.019(2) 0.051(3) 0.053(3) 0.008(2) -0.0018(18) 0.0073(18) C21 0.032(2) 0.043(2) 0.034(2) 0.0125(18) -0.0005(18) 0.0112(18) C22 0.0254(19) 0.0310(19) 0.026(2) 0.0080(15) 0.0066(16) 0.0067(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O3 2.020(2) 2_666 ? Ni1 O9 2.040(2) . ? Ni1 O2W 2.049(2) . ? Ni1 N2 2.077(3) . ? Ni1 N1 2.115(3) . ? Ni1 O1W 2.124(2) . ? O1 P1 1.521(2) . ? O2 P1 1.585(2) . ? O3 P1 1.489(2) . ? O3 Ni1 2.020(2) 2_666 ? O4 P2 1.578(2) . ? O5 P2 1.490(2) . ? O6 P2 1.530(2) . ? O7 P3 1.547(2) . ? O8 P3 1.559(2) . ? O9 P3 1.483(2) . ? N1 C13 1.338(4) . ? N1 C17 1.350(4) . ? N2 C18 1.340(4) . ? N2 C22 1.346(4) . ? P1 C7 1.811(3) . ? P2 C9 1.810(3) . ? P3 C11 1.798(3) . ? C1 C2 1.410(4) . ? C1 C6 1.411(4) . ? C1 C7 1.508(4) . ? C2 C3 1.396(4) . ? C2 C8 1.519(4) . ? C3 C4 1.401(4) . ? C3 C9 1.527(4) . ? C4 C5 1.410(4) . ? C4 C10 1.510(4) . ? C5 C6 1.393(4) . ? C5 C11 1.516(4) . ? C6 C12 1.516(4) . ? C13 C14 1.383(5) . ? C14 C15 1.363(5) . ? C15 C16 1.385(5) . ? C16 C17 1.382(5) . ? C17 C18 1.480(4) . ? C18 C19 1.380(5) . ? C19 C20 1.391(5) . ? C20 C21 1.375(5) . ? C21 C22 1.361(5) . ? 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 O3 Ni1 O9 93.10(9) 2_666 . ? O3 Ni1 O2W 84.70(8) 2_666 . ? O9 Ni1 O2W 89.66(9) . . ? O3 Ni1 N2 89.81(10) 2_666 . ? O9 Ni1 N2 177.09(10) . . ? O2W Ni1 N2 90.79(9) . . ? O3 Ni1 N1 95.34(9) 2_666 . ? O9 Ni1 N1 101.50(9) . . ? O2W Ni1 N1 168.81(10) . . ? N2 Ni1 N1 78.03(10) . . ? O3 Ni1 O1W 178.20(9) 2_666 . ? O9 Ni1 O1W 85.99(9) . . ? O2W Ni1 O1W 93.75(8) . . ? N2 Ni1 O1W 91.11(9) . . ? N1 Ni1 O1W 86.36(9) . . ? P1 O3 Ni1 140.76(13) . 2_666 ? P3 O9 Ni1 150.73(14) . . ? C13 N1 C17 118.5(3) . . ? C13 N1 Ni1 127.1(2) . . ? C17 N1 Ni1 114.4(2) . . ? C18 N2 C22 118.1(3) . . ? C18 N2 Ni1 116.5(2) . . ? C22 N2 Ni1 125.4(2) . . ? O3 P1 O1 117.64(12) . . ? O3 P1 O2 107.17(12) . . ? O1 P1 O2 108.47(12) . . ? O3 P1 C7 108.20(14) . . ? O1 P1 C7 108.34(14) . . ? O2 P1 C7 106.50(13) . . ? O5 P2 O6 115.04(12) . . ? O5 P2 O4 111.58(12) . . ? O6 P2 O4 105.20(12) . . ? O5 P2 C9 111.74(13) . . ? O6 P2 C9 105.84(13) . . ? O4 P2 C9 106.86(13) . . ? O9 P3 O7 113.55(13) . . ? O9 P3 O8 112.40(13) . . ? O7 P3 O8 106.18(12) . . ? O9 P3 C11 113.85(13) . . ? O7 P3 C11 103.06(13) . . ? O8 P3 C11 107.03(14) . . ? C2 C1 C6 119.8(3) . . ? C2 C1 C7 120.5(3) . . ? C6 C1 C7 119.6(3) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 C8 121.0(3) . . ? C1 C2 C8 119.2(3) . . ? C2 C3 C4 120.8(3) . . ? C2 C3 C9 119.3(3) . . ? C4 C3 C9 119.9(3) . . ? C3 C4 C5 119.0(3) . . ? C3 C4 C10 121.3(3) . . ? C5 C4 C10 119.7(3) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 C11 120.7(3) . . ? C4 C5 C11 118.3(3) . . ? C5 C6 C1 119.6(3) . . ? C5 C6 C12 120.9(3) . . ? C1 C6 C12 119.4(3) . . ? C1 C7 P1 114.3(2) . . ? C3 C9 P2 115.8(2) . . ? C5 C11 P3 112.2(2) . . ? N1 C13 C14 122.8(3) . . ? C15 C14 C13 118.8(3) . . ? C14 C15 C16 119.2(3) . . ? C17 C16 C15 119.5(3) . . ? N1 C17 C16 121.2(3) . . ? N1 C17 C18 115.9(3) . . ? C16 C17 C18 122.8(3) . . ? N2 C18 C19 121.9(3) . . ? N2 C18 C17 115.1(3) . . ? C19 C18 C17 123.0(3) . . ? C18 C19 C20 119.3(3) . . ? C21 C20 C19 118.4(4) . . ? C22 C21 C20 119.2(3) . . ? N2 C22 C21 123.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O6 0.85 1.93 2.770(3) 167.8 2_665 O2W H3W O5 0.85 2.01 2.802(3) 154.4 . O2W H4W O5 0.85 1.83 2.681(3) 175.9 2_665 O2 H2A O1 0.82 1.77 2.574(3) 168.4 2_666 O7 H7C O6 0.82 1.72 2.524(3) 167.4 1_545 O8 H8D O1 0.82 1.74 2.558(3) 173.5 2_666 O1W H2W O6 0.85 2.16 3.003(3) 169.0 1_545 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.21 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.583 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.085 data_5 _database_code_depnum_ccdc_archive 'CCDC 900078' #TrackingRef '5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H27 Cu N2 O9 P3' _chemical_formula_weight 619.91 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 '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 9.7878(16) _cell_length_b 10.2010(16) _cell_length_c 14.443(3) _cell_angle_alpha 76.790(2) _cell_angle_beta 81.902(2) _cell_angle_gamma 66.9930(10) _cell_volume 1290.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7317 _cell_measurement_theta_min 1.45 _cell_measurement_theta_max 25 _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7317 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4468 _reflns_number_gt 3469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.7184P] 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 4468 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.19229(5) -0.05501(4) 0.83356(3) 0.02134(15) Uani 1 1 d . . . O1 O 0.0004(3) 0.1481(3) 0.5553(2) 0.0369(7) Uani 1 1 d . . . H1A H -0.0367 0.1299 0.5147 0.055 Uiso 1 1 calc R . . O2 O 0.1915(3) 0.0293(3) 0.67632(18) 0.0327(7) Uani 1 1 d . . . O3 O 0.1463(3) -0.1206(3) 0.57358(19) 0.0348(7) Uani 1 1 d . . . O4 O -0.1815(3) 0.4439(3) 0.1171(2) 0.0354(7) Uani 1 1 d . . . H4A H -0.1857 0.5179 0.1327 0.053 Uiso 1 1 calc R . . O5 O -0.1503(3) 0.3280(3) 0.2868(2) 0.0371(7) Uani 1 1 d . . . H5A H -0.1367 0.2475 0.3199 0.056 Uiso 1 1 calc R . . O6 O -0.0732(3) 0.1732(3) 0.15916(19) 0.0287(6) Uani 1 1 d . . . O7 O 0.7622(4) -0.3082(3) 0.1251(2) 0.0461(8) Uani 1 1 d . . . O8 O 0.7657(3) -0.2484(3) 0.2832(2) 0.0416(8) Uani 1 1 d . . . H8D H 0.7800 -0.1812 0.2968 0.062 Uiso 1 1 calc R . . O9 O 0.6920(3) -0.0490(2) 0.13915(18) 0.0245(6) Uani 1 1 d . . . N1 N 0.0010(3) 0.1112(3) 0.8520(2) 0.0219(7) Uani 1 1 d . . . N2 N -0.6162(3) 0.7757(3) 0.8317(2) 0.0247(7) Uani 1 1 d . . . P1 P 0.15318(11) 0.02209(12) 0.58044(7) 0.0289(3) Uani 1 1 d . . . P2 P -0.08393(11) 0.31136(10) 0.18398(7) 0.0258(2) Uani 1 1 d . . . P3 P 0.68883(11) -0.19560(10) 0.18638(8) 0.0269(2) Uani 1 1 d . . . C1 C 0.2941(4) 0.0602(5) 0.3928(3) 0.0323(10) Uani 1 1 d . . . C2 C 0.2120(5) 0.1890(5) 0.3323(3) 0.0337(10) Uani 1 1 d . . . C3 C 0.2091(4) 0.1884(4) 0.2354(3) 0.0303(9) Uani 1 1 d . . . C4 C 0.3032(4) 0.0672(4) 0.1975(3) 0.0291(9) Uani 1 1 d . . . C5 C 0.3930(4) -0.0595(4) 0.2579(3) 0.0311(9) Uani 1 1 d . . . C6 C 0.3792(4) -0.0654(5) 0.3566(3) 0.0329(10) Uani 1 1 d . . . C7 C 0.2953(5) 0.0602(5) 0.4980(3) 0.0374(10) Uani 1 1 d . . . H7A H 0.2916 0.1548 0.5030 0.045 Uiso 1 1 calc R . . H7B H 0.3906 -0.0100 0.5199 0.045 Uiso 1 1 calc R . . C8 C 0.1310(5) 0.3267(5) 0.3707(3) 0.0438(11) Uani 1 1 d . . . H8A H 0.1436 0.3076 0.4378 0.066 Uiso 1 1 calc R . . H8B H 0.0271 0.3614 0.3599 0.066 Uiso 1 1 calc R . . H8C H 0.1707 0.3988 0.3389 0.066 Uiso 1 1 calc R . . C9 C 0.0991(4) 0.3167(4) 0.1739(3) 0.0328(10) Uani 1 1 d . . . H9A H 0.1365 0.3198 0.1079 0.039 Uiso 1 1 calc R . . H9B H 0.0923 0.4053 0.1918 0.039 Uiso 1 1 calc R . . C10 C 0.3114(5) 0.0690(5) 0.0921(3) 0.0429(11) Uani 1 1 d . . . H10A H 0.2437 0.1606 0.0610 0.064 Uiso 1 1 calc R . . H10B H 0.2849 -0.0077 0.0822 0.064 Uiso 1 1 calc R . . H10C H 0.4108 0.0554 0.0661 0.064 Uiso 1 1 calc R . . C11 C 0.4993(4) -0.1864(4) 0.2155(3) 0.0341(10) Uani 1 1 d . . . H11A H 0.4588 -0.1858 0.1577 0.041 Uiso 1 1 calc R . . H11B H 0.5024 -0.2746 0.2598 0.041 Uiso 1 1 calc R . . C12 C 0.4536(5) -0.2078(5) 0.4228(3) 0.0460(12) Uani 1 1 d . . . H12A H 0.4341 -0.1935 0.4875 0.069 Uiso 1 1 calc R . . H12B H 0.5589 -0.2427 0.4078 0.069 Uiso 1 1 calc R . . H12C H 0.4149 -0.2776 0.4151 0.069 Uiso 1 1 calc R . . C25 C -0.0252(4) 0.1905(4) 0.9191(3) 0.0299(9) Uani 1 1 d . . . H25A H 0.0395 0.1565 0.9681 0.036 Uiso 1 1 calc R . . C26 C -0.1438(4) 0.3204(4) 0.9190(3) 0.0300(9) Uani 1 1 d . . . H26A H -0.1589 0.3712 0.9679 0.036 Uiso 1 1 calc R . . C27 C -0.2402(4) 0.3749(4) 0.8460(3) 0.0230(8) Uani 1 1 d . . . C28 C -0.3667(4) 0.5176(4) 0.8399(3) 0.0221(8) Uani 1 1 d . . . C29 C -0.4150(4) 0.5891(4) 0.9171(3) 0.0271(9) Uani 1 1 d . . . H29A H -0.3644 0.5515 0.9729 0.033 Uiso 1 1 calc R . . C30 C -0.5380(4) 0.7155(4) 0.9096(3) 0.0293(9) Uani 1 1 d . . . H30A H -0.5686 0.7619 0.9615 0.035 Uiso 1 1 calc R . . C31 C -0.5643(4) 0.7114(4) 0.7560(3) 0.0308(9) Uani 1 1 d . . . H31A H -0.6127 0.7550 0.6996 0.037 Uiso 1 1 calc R . . C32 C -0.4433(4) 0.5845(4) 0.7580(3) 0.0315(9) Uani 1 1 d . . . H32A H -0.4125 0.5431 0.7039 0.038 Uiso 1 1 calc R . . C33 C -0.2141(4) 0.2902(4) 0.7781(3) 0.0273(9) Uani 1 1 d . . . H33A H -0.2766 0.3219 0.7281 0.033 Uiso 1 1 calc R . . C34 C -0.0963(4) 0.1595(4) 0.7845(3) 0.0278(9) Uani 1 1 d . . . H34A H -0.0840 0.1023 0.7398 0.033 Uiso 1 1 calc R . . 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 Cu1 0.0144(2) 0.0130(2) 0.0326(3) -0.00707(18) -0.00263(18) 0.00115(17) O1 0.0293(16) 0.0441(17) 0.0352(17) -0.0068(13) -0.0125(13) -0.0081(13) O2 0.0300(15) 0.0435(16) 0.0227(15) -0.0057(12) -0.0055(12) -0.0107(13) O3 0.0360(16) 0.0404(16) 0.0299(16) -0.0054(13) -0.0064(12) -0.0154(13) O4 0.0468(18) 0.0172(13) 0.0401(17) -0.0087(12) -0.0142(14) -0.0040(12) O5 0.0410(17) 0.0288(15) 0.0386(18) -0.0085(13) 0.0027(13) -0.0105(13) O6 0.0221(14) 0.0171(12) 0.0460(17) -0.0092(12) -0.0017(12) -0.0045(11) O7 0.058(2) 0.0222(14) 0.054(2) -0.0165(13) 0.0078(16) -0.0084(14) O8 0.0473(19) 0.0338(16) 0.0422(19) 0.0059(13) -0.0167(14) -0.0160(14) O9 0.0216(14) 0.0180(12) 0.0332(15) -0.0072(11) -0.0048(11) -0.0042(10) N1 0.0160(16) 0.0152(14) 0.0315(18) -0.0068(13) -0.0034(13) -0.0006(12) N2 0.0174(16) 0.0187(15) 0.036(2) -0.0075(14) -0.0041(14) -0.0023(13) P1 0.0249(6) 0.0395(6) 0.0219(6) -0.0049(4) -0.0031(4) -0.0114(5) P2 0.0269(6) 0.0178(5) 0.0317(6) -0.0047(4) -0.0042(4) -0.0063(4) P3 0.0269(5) 0.0185(5) 0.0336(6) -0.0071(4) -0.0017(4) -0.0057(4) C1 0.027(2) 0.048(3) 0.026(2) -0.0043(19) -0.0009(17) -0.0191(19) C2 0.036(2) 0.045(2) 0.029(2) -0.0078(19) -0.0009(18) -0.025(2) C3 0.028(2) 0.038(2) 0.031(2) -0.0023(18) -0.0029(17) -0.0208(19) C4 0.024(2) 0.042(2) 0.027(2) -0.0052(18) -0.0022(16) -0.0189(18) C5 0.023(2) 0.042(2) 0.034(2) -0.0054(18) 0.0003(17) -0.0189(19) C6 0.025(2) 0.046(2) 0.028(2) -0.0006(19) -0.0038(17) -0.0163(19) C7 0.027(2) 0.057(3) 0.026(2) -0.006(2) -0.0011(17) -0.015(2) C8 0.056(3) 0.039(2) 0.040(3) -0.010(2) -0.001(2) -0.020(2) C9 0.038(2) 0.037(2) 0.031(2) -0.0037(18) -0.0052(18) -0.022(2) C10 0.039(3) 0.052(3) 0.033(3) -0.010(2) -0.004(2) -0.009(2) C11 0.035(2) 0.039(2) 0.035(2) -0.0084(19) -0.0019(19) -0.021(2) C12 0.041(3) 0.050(3) 0.034(3) 0.002(2) -0.003(2) -0.010(2) C25 0.027(2) 0.026(2) 0.031(2) -0.0086(17) -0.0037(17) -0.0007(17) C26 0.025(2) 0.027(2) 0.030(2) -0.0148(17) -0.0053(17) 0.0051(17) C27 0.0155(18) 0.0193(18) 0.033(2) -0.0092(16) 0.0026(16) -0.0041(15) C28 0.0155(18) 0.0156(17) 0.030(2) -0.0037(15) -0.0007(15) -0.0013(14) C29 0.022(2) 0.0218(18) 0.033(2) -0.0077(16) -0.0051(16) 0.0002(16) C30 0.026(2) 0.0225(19) 0.037(2) -0.0144(17) 0.0032(18) -0.0033(16) C31 0.025(2) 0.0231(19) 0.037(2) -0.0077(17) -0.0082(18) 0.0020(16) C32 0.031(2) 0.025(2) 0.033(2) -0.0136(17) -0.0033(18) -0.0003(17) C33 0.020(2) 0.0232(19) 0.037(2) -0.0079(17) -0.0083(16) -0.0023(16) C34 0.022(2) 0.0237(19) 0.039(2) -0.0159(17) -0.0019(17) -0.0033(16) _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 Cu1 O9 1.954(2) 2_656 ? Cu1 O6 1.957(3) 2_556 ? Cu1 N2 1.993(3) 1_645 ? Cu1 N1 2.008(3) . ? Cu1 O2 2.237(3) . ? O1 P1 1.568(3) . ? O1 H1A 0.8200 . ? O2 P1 1.509(3) . ? O3 P1 1.510(3) . ? O4 P2 1.526(3) . ? O4 H4A 0.8200 . ? O5 P2 1.554(3) . ? O5 H5A 0.8200 . ? O6 P2 1.493(3) . ? O6 Cu1 1.957(3) 2_556 ? O7 P3 1.503(3) . ? O8 P3 1.564(3) . ? O8 H8D 0.8200 . ? O9 P3 1.506(3) . ? O9 Cu1 1.954(2) 2_656 ? N1 C34 1.333(5) . ? N1 C25 1.336(5) . ? N2 C30 1.338(5) . ? N2 C31 1.338(5) . ? N2 Cu1 1.993(3) 1_465 ? P1 C7 1.803(4) . ? P2 C9 1.798(4) . ? P3 C11 1.813(4) . ? C1 C6 1.399(6) . ? C1 C2 1.409(6) . ? C1 C7 1.520(6) . ? C2 C3 1.406(6) . ? C2 C8 1.507(6) . ? C3 C4 1.397(6) . ? C3 C9 1.515(6) . ? C4 C5 1.419(5) . ? C4 C10 1.509(6) . ? C5 C6 1.403(6) . ? C5 C11 1.504(6) . ? C6 C12 1.513(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C25 C26 1.378(5) . ? C25 H25A 0.9300 . ? C26 C27 1.384(5) . ? C26 H26A 0.9300 . ? C27 C33 1.384(5) . ? C27 C28 1.492(5) . ? C28 C32 1.381(5) . ? C28 C29 1.397(5) . ? C29 C30 1.372(5) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 C32 1.369(5) . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? C33 C34 1.374(5) . ? C33 H33A 0.9300 . ? C34 H34A 0.9300 . ? 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 O9 Cu1 O6 165.68(11) 2_656 2_556 ? O9 Cu1 N2 86.61(11) 2_656 1_645 ? O6 Cu1 N2 92.99(11) 2_556 1_645 ? O9 Cu1 N1 91.27(11) 2_656 . ? O6 Cu1 N1 87.49(11) 2_556 . ? N2 Cu1 N1 173.32(13) 1_645 . ? O9 Cu1 O2 95.92(10) 2_656 . ? O6 Cu1 O2 98.34(11) 2_556 . ? N2 Cu1 O2 96.59(12) 1_645 . ? N1 Cu1 O2 89.93(11) . . ? P1 O1 H1A 109.5 . . ? P1 O2 Cu1 147.46(18) . . ? P2 O4 H4A 109.5 . . ? P2 O5 H5A 109.5 . . ? P2 O6 Cu1 140.54(16) . 2_556 ? P3 O8 H8D 109.5 . . ? P3 O9 Cu1 129.97(16) . 2_656 ? C34 N1 C25 117.3(3) . . ? C34 N1 Cu1 117.6(2) . . ? C25 N1 Cu1 124.2(3) . . ? C30 N2 C31 116.9(3) . . ? C30 N2 Cu1 120.5(2) . 1_465 ? C31 N2 Cu1 122.5(3) . 1_465 ? O2 P1 O3 115.08(16) . . ? O2 P1 O1 108.07(16) . . ? O3 P1 O1 109.79(16) . . ? O2 P1 C7 104.72(18) . . ? O3 P1 C7 110.76(19) . . ? O1 P1 C7 108.10(18) . . ? O6 P2 O4 111.74(16) . . ? O6 P2 O5 113.16(15) . . ? O4 P2 O5 106.73(16) . . ? O6 P2 C9 108.94(17) . . ? O4 P2 C9 108.07(17) . . ? O5 P2 C9 108.01(18) . . ? O7 P3 O9 112.96(16) . . ? O7 P3 O8 109.32(18) . . ? O9 P3 O8 110.01(16) . . ? O7 P3 C11 107.25(19) . . ? O9 P3 C11 110.98(17) . . ? O8 P3 C11 106.04(18) . . ? C6 C1 C2 120.8(4) . . ? C6 C1 C7 119.8(4) . . ? C2 C1 C7 119.3(4) . . ? C3 C2 C1 119.3(4) . . ? C3 C2 C8 120.4(4) . . ? C1 C2 C8 120.3(4) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 C9 120.6(4) . . ? C2 C3 C9 119.6(4) . . ? C3 C4 C5 120.3(4) . . ? C3 C4 C10 120.6(4) . . ? C5 C4 C10 119.0(4) . . ? C6 C5 C4 119.3(4) . . ? C6 C5 C11 120.9(4) . . ? C4 C5 C11 119.7(4) . . ? C1 C6 C5 119.5(4) . . ? C1 C6 C12 120.7(4) . . ? C5 C6 C12 119.7(4) . . ? C1 C7 P1 119.8(3) . . ? C1 C7 H7A 107.4 . . ? P1 C7 H7A 107.4 . . ? C1 C7 H7B 107.4 . . ? P1 C7 H7B 107.4 . . ? H7A C7 H7B 106.9 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 P2 113.6(3) . . ? C3 C9 H9A 108.8 . . ? P2 C9 H9A 108.8 . . ? C3 C9 H9B 108.8 . . ? P2 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 P3 117.2(3) . . ? C5 C11 H11A 108.0 . . ? P3 C11 H11A 108.0 . . ? C5 C11 H11B 108.0 . . ? P3 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C25 C26 123.1(4) . . ? N1 C25 H25A 118.5 . . ? C26 C25 H25A 118.5 . . ? C25 C26 C27 119.7(4) . . ? C25 C26 H26A 120.2 . . ? C27 C26 H26A 120.2 . . ? C26 C27 C33 116.8(3) . . ? C26 C27 C28 122.1(3) . . ? C33 C27 C28 121.1(3) . . ? C32 C28 C29 116.8(3) . . ? C32 C28 C27 121.5(3) . . ? C29 C28 C27 121.7(3) . . ? C30 C29 C28 119.2(4) . . ? C30 C29 H29A 120.4 . . ? C28 C29 H29A 120.4 . . ? N2 C30 C29 123.6(4) . . ? N2 C30 H30A 118.2 . . ? C29 C30 H30A 118.2 . . ? N2 C31 C32 123.0(4) . . ? N2 C31 H31A 118.5 . . ? C32 C31 H31A 118.5 . . ? C31 C32 C28 120.4(4) . . ? C31 C32 H32A 119.8 . . ? C28 C32 H32A 119.8 . . ? C34 C33 C27 120.3(4) . . ? C34 C33 H33A 119.9 . . ? C27 C33 H33A 119.9 . . ? N1 C34 C33 122.7(3) . . ? N1 C34 H34A 118.6 . . ? C33 C34 H34A 118.6 . . ? 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 O9 Cu1 O2 P1 172.4(3) 2_656 . . . ? O6 Cu1 O2 P1 -8.8(3) 2_556 . . . ? N2 Cu1 O2 P1 85.2(3) 1_645 . . . ? N1 Cu1 O2 P1 -96.3(3) . . . . ? O9 Cu1 N1 C34 130.3(3) 2_656 . . . ? O6 Cu1 N1 C34 -64.0(3) 2_556 . . . ? N2 Cu1 N1 C34 -158.3(10) 1_645 . . . ? O2 Cu1 N1 C34 34.4(3) . . . . ? O9 Cu1 N1 C25 -38.9(3) 2_656 . . . ? O6 Cu1 N1 C25 126.8(3) 2_556 . . . ? N2 Cu1 N1 C25 32.5(12) 1_645 . . . ? O2 Cu1 N1 C25 -134.8(3) . . . . ? Cu1 O2 P1 O3 -24.8(4) . . . . ? Cu1 O2 P1 O1 98.3(3) . . . . ? Cu1 O2 P1 C7 -146.6(3) . . . . ? Cu1 O6 P2 O4 -73.1(3) 2_556 . . . ? Cu1 O6 P2 O5 47.4(3) 2_556 . . . ? Cu1 O6 P2 C9 167.5(2) 2_556 . . . ? Cu1 O9 P3 O7 -108.2(2) 2_656 . . . ? Cu1 O9 P3 O8 14.2(2) 2_656 . . . ? Cu1 O9 P3 C11 131.3(2) 2_656 . . . ? C6 C1 C2 C3 3.7(6) . . . . ? C7 C1 C2 C3 -179.0(3) . . . . ? C6 C1 C2 C8 -175.0(4) . . . . ? C7 C1 C2 C8 2.3(6) . . . . ? C1 C2 C3 C4 -8.9(6) . . . . ? C8 C2 C3 C4 169.8(4) . . . . ? C1 C2 C3 C9 168.5(4) . . . . ? C8 C2 C3 C9 -12.9(6) . . . . ? C2 C3 C4 C5 5.0(6) . . . . ? C9 C3 C4 C5 -172.3(3) . . . . ? C2 C3 C4 C10 -174.8(4) . . . . ? C9 C3 C4 C10 7.9(6) . . . . ? C3 C4 C5 C6 4.1(6) . . . . ? C10 C4 C5 C6 -176.0(4) . . . . ? C3 C4 C5 C11 -177.0(3) . . . . ? C10 C4 C5 C11 2.9(5) . . . . ? C2 C1 C6 C5 5.5(6) . . . . ? C7 C1 C6 C5 -171.8(4) . . . . ? C2 C1 C6 C12 -173.2(4) . . . . ? C7 C1 C6 C12 9.5(6) . . . . ? C4 C5 C6 C1 -9.3(6) . . . . ? C11 C5 C6 C1 171.8(4) . . . . ? C4 C5 C6 C12 169.4(4) . . . . ? C11 C5 C6 C12 -9.5(6) . . . . ? C6 C1 C7 P1 -94.5(4) . . . . ? C2 C1 C7 P1 88.1(4) . . . . ? O2 P1 C7 C1 179.1(3) . . . . ? O3 P1 C7 C1 54.5(4) . . . . ? O1 P1 C7 C1 -65.8(4) . . . . ? C4 C3 C9 P2 95.2(4) . . . . ? C2 C3 C9 P2 -82.1(4) . . . . ? O6 P2 C9 C3 -57.0(3) . . . . ? O4 P2 C9 C3 -178.6(3) . . . . ? O5 P2 C9 C3 66.3(3) . . . . ? C6 C5 C11 P3 -87.9(4) . . . . ? C4 C5 C11 P3 93.2(4) . . . . ? O7 P3 C11 C5 -166.8(3) . . . . ? O9 P3 C11 C5 -43.0(4) . . . . ? O8 P3 C11 C5 76.4(3) . . . . ? C34 N1 C25 C26 -2.5(6) . . . . ? Cu1 N1 C25 C26 166.7(3) . . . . ? N1 C25 C26 C27 -1.2(6) . . . . ? C25 C26 C27 C33 2.7(6) . . . . ? C25 C26 C27 C28 -177.5(3) . . . . ? C26 C27 C28 C32 166.7(4) . . . . ? C33 C27 C28 C32 -13.5(5) . . . . ? C26 C27 C28 C29 -14.3(5) . . . . ? C33 C27 C28 C29 165.5(4) . . . . ? C32 C28 C29 C30 3.2(5) . . . . ? C27 C28 C29 C30 -175.8(3) . . . . ? C31 N2 C30 C29 -4.0(6) . . . . ? Cu1 N2 C30 C29 172.0(3) 1_465 . . . ? C28 C29 C30 N2 0.1(6) . . . . ? C30 N2 C31 C32 4.5(6) . . . . ? Cu1 N2 C31 C32 -171.4(3) 1_465 . . . ? N2 C31 C32 C28 -1.1(6) . . . . ? C29 C28 C32 C31 -2.8(6) . . . . ? C27 C28 C32 C31 176.3(4) . . . . ? C26 C27 C33 C34 -0.7(5) . . . . ? C28 C27 C33 C34 179.5(3) . . . . ? C25 N1 C34 C33 4.6(5) . . . . ? Cu1 N1 C34 C33 -165.3(3) . . . . ? C27 C33 C34 N1 -3.1(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O3 0.82 1.82 2.628(4) 169.6 2_556 O4 H4A O7 0.82 1.62 2.395(4) 155.6 1_465 O5 H5A O3 0.82 1.79 2.559(4) 156.0 2_556 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.953 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.081 data_6 _database_code_depnum_ccdc_archive 'CCDC 900079' #TrackingRef '6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H29 Cu N2 O10 P3' _chemical_formula_weight 661.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 10.1684(7) _cell_length_b 15.3969(11) _cell_length_c 16.7062(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.6080(10) _cell_angle_gamma 90.00 _cell_volume 2612.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 14458 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 1.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14458 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4585 _reflns_number_gt 3992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0443P)^2^+2.3994P] 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 4585 _refine_ls_number_parameters 371 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.95333(3) 0.899262(19) 0.226186(17) 0.02210(10) Uani 1 1 d . . . O1 O 1.22767(19) 0.58898(13) -0.08915(11) 0.0386(5) Uani 1 1 d . . . H1A H 1.1995 0.5785 -0.1349 0.058 Uiso 1 1 calc R . . O2 O 1.44519(19) 0.61339(12) -0.15672(10) 0.0324(4) Uani 1 1 d . . . O3 O 1.31832(17) 0.73842(12) -0.09896(10) 0.0299(4) Uani 1 1 d . . . H3A H 1.3690 0.7635 -0.1280 0.045 Uiso 1 1 calc R . . O4 O 1.73927(16) 0.87934(11) 0.18758(11) 0.0270(4) Uani 1 1 d . . . O5 O 1.66726(16) 1.02974(11) 0.15575(10) 0.0258(4) Uani 1 1 d . . . H5A H 1.6194 1.0689 0.1705 0.039 Uiso 1 1 calc R . . O6 O 1.59810(17) 0.96187(12) 0.28514(10) 0.0297(4) Uani 1 1 d . . . O7 O 0.99694(17) 0.77980(11) 0.20427(11) 0.0305(4) Uani 1 1 d . . . O8 O 0.97412(18) 0.62451(12) 0.17023(11) 0.0319(4) Uani 1 1 d . . . H8D H 0.9554 0.5782 0.1910 0.048 Uiso 1 1 calc R . . O9 O 0.95887(18) 0.66832(11) 0.31467(11) 0.0300(4) Uani 1 1 d . . . N1 N 1.05892(19) 0.93549(13) 0.13090(11) 0.0218(4) Uani 1 1 d . . . N2 N 0.93790(18) 1.02948(13) 0.23742(11) 0.0221(4) Uani 1 1 d . . . P1 P 1.35700(6) 0.64139(4) -0.09229(4) 0.02309(15) Uani 1 1 d . . . P2 P 1.63000(6) 0.94264(4) 0.19817(4) 0.01957(14) Uani 1 1 d . . . P3 P 1.02221(6) 0.69077(4) 0.23718(4) 0.02164(15) Uani 1 1 d . . . C1 C 1.4066(2) 0.68311(15) 0.07178(13) 0.0202(5) Uani 1 1 d . . . C2 C 1.4611(2) 0.76629(16) 0.07861(14) 0.0218(5) Uani 1 1 d . . . C3 C 1.4258(2) 0.82059(15) 0.14172(14) 0.0205(5) Uani 1 1 d . . . C4 C 1.3393(2) 0.79116(15) 0.19870(14) 0.0204(5) Uani 1 1 d . . . C5 C 1.2875(2) 0.70674(15) 0.19253(14) 0.0205(5) Uani 1 1 d . . . C6 C 1.3202(2) 0.65235(15) 0.12847(14) 0.0216(5) Uani 1 1 d . . . C7 C 1.4442(3) 0.62441(17) 0.00300(15) 0.0262(5) Uani 1 1 d . . . H7A H 1.4307 0.5646 0.0190 0.031 Uiso 1 1 calc R . . H7B H 1.5375 0.6317 -0.0047 0.031 Uiso 1 1 calc R . . C8 C 1.5603(3) 0.7985(2) 0.02085(17) 0.0387(7) Uani 1 1 d . . . H8A H 1.5746 0.7545 -0.0186 0.058 Uiso 1 1 calc R . . H8B H 1.6419 0.8111 0.0497 0.058 Uiso 1 1 calc R . . H8C H 1.5275 0.8501 -0.0052 0.058 Uiso 1 1 calc R . . C9 C 1.4765(2) 0.91378(16) 0.14368(15) 0.0247(5) Uani 1 1 d . . . H9A H 1.4078 0.9495 0.1651 0.030 Uiso 1 1 calc R . . H9B H 1.4851 0.9317 0.0885 0.030 Uiso 1 1 calc R . . C10 C 1.3035(3) 0.85107(18) 0.26654(16) 0.0305(6) Uani 1 1 d . . . H10A H 1.3478 0.9057 0.2613 0.046 Uiso 1 1 calc R . . H10B H 1.3298 0.8250 0.3169 0.046 Uiso 1 1 calc R . . H10C H 1.2100 0.8604 0.2643 0.046 Uiso 1 1 calc R . . C11 C 1.1973(2) 0.67351(17) 0.25560(15) 0.0249(5) Uani 1 1 d . . . H11A H 1.2232 0.7008 0.3062 0.030 Uiso 1 1 calc R . . H11B H 1.2122 0.6116 0.2619 0.030 Uiso 1 1 calc R . . C12 C 1.2680(3) 0.56035(17) 0.12192(17) 0.0343(6) Uani 1 1 d . . . H12A H 1.2993 0.5335 0.0746 0.051 Uiso 1 1 calc R . . H12B H 1.1735 0.5615 0.1189 0.051 Uiso 1 1 calc R . . H12C H 1.2980 0.5277 0.1682 0.051 Uiso 1 1 calc R . . C13 C 0.8743(2) 1.07495(17) 0.29113(15) 0.0266(5) Uani 1 1 d . . . H13A H 0.8426 1.0461 0.3352 0.032 Uiso 1 1 calc R . . C14 C 0.8533(2) 1.16387(18) 0.28414(16) 0.0305(6) Uani 1 1 d . . . H14A H 0.8073 1.1933 0.3226 0.037 Uiso 1 1 calc R . . C15 C 0.9006(2) 1.20796(17) 0.22028(16) 0.0302(6) Uani 1 1 d . . . H15A H 0.8851 1.2672 0.2144 0.036 Uiso 1 1 calc R . . C16 C 0.9726(2) 1.16308(16) 0.16380(15) 0.0265(5) Uani 1 1 d . . . C17 C 1.0312(3) 1.20257(17) 0.09661(17) 0.0334(6) Uani 1 1 d . . . H17A H 1.0192 1.2617 0.0873 0.040 Uiso 1 1 calc R . . C18 C 1.1038(3) 1.15562(18) 0.04637(16) 0.0327(6) Uani 1 1 d . . . H18A H 1.1438 1.1835 0.0045 0.039 Uiso 1 1 calc R . . C19 C 1.1203(2) 1.06386(17) 0.05625(15) 0.0259(5) Uani 1 1 d . . . C20 C 1.1911(2) 1.00992(19) 0.00555(15) 0.0308(6) Uani 1 1 d . . . H20A H 1.2355 1.0338 -0.0366 0.037 Uiso 1 1 calc R . . C21 C 1.1945(2) 0.92251(19) 0.01847(15) 0.0304(6) Uani 1 1 d . . . H21A H 1.2426 0.8868 -0.0143 0.037 Uiso 1 1 calc R . . C22 C 1.1255(2) 0.88654(17) 0.08117(14) 0.0247(5) Uani 1 1 d . . . H22A H 1.1264 0.8266 0.0882 0.030 Uiso 1 1 calc R . . C23 C 1.0580(2) 1.02299(16) 0.11937(14) 0.0213(5) Uani 1 1 d . . . C24 C 0.9874(2) 1.07331(16) 0.17503(14) 0.0216(5) Uani 1 1 d . . . O1W O 1.8164(10) 0.6231(6) 0.0195(5) 0.155(5) Uani 0.592(10) 1 d PU A 1 O1W' O 1.9874(16) 0.5920(11) -0.0031(8) 0.185(8) Uani 0.408(10) 1 d PU 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 Cu1 0.02633(17) 0.01980(17) 0.02065(17) 0.00197(12) 0.00621(12) -0.00043(12) O1 0.0417(11) 0.0501(13) 0.0238(10) -0.0040(9) 0.0002(8) -0.0195(10) O2 0.0405(11) 0.0363(11) 0.0207(9) -0.0052(8) 0.0043(8) 0.0033(8) O3 0.0304(9) 0.0324(10) 0.0274(9) 0.0056(8) 0.0077(8) 0.0052(8) O4 0.0212(8) 0.0212(9) 0.0383(10) -0.0023(8) -0.0024(7) 0.0015(7) O5 0.0267(9) 0.0185(9) 0.0328(10) -0.0008(7) 0.0064(7) 0.0004(7) O6 0.0261(9) 0.0397(11) 0.0232(9) 0.0005(8) 0.0009(7) 0.0034(8) O7 0.0335(10) 0.0221(9) 0.0366(10) 0.0035(8) 0.0093(8) 0.0048(8) O8 0.0362(10) 0.0280(10) 0.0313(10) -0.0029(8) 0.0003(8) -0.0069(8) O9 0.0342(10) 0.0227(9) 0.0345(10) -0.0009(8) 0.0162(8) -0.0057(8) N1 0.0213(10) 0.0238(11) 0.0200(10) 0.0021(8) -0.0012(8) 0.0012(8) N2 0.0205(10) 0.0239(11) 0.0217(10) -0.0016(8) -0.0001(8) -0.0030(8) P1 0.0267(3) 0.0255(3) 0.0173(3) -0.0025(3) 0.0027(2) -0.0027(3) P2 0.0181(3) 0.0183(3) 0.0223(3) -0.0005(2) 0.0001(2) -0.0009(2) P3 0.0212(3) 0.0186(3) 0.0256(3) -0.0005(2) 0.0056(3) -0.0021(2) C1 0.0198(11) 0.0237(13) 0.0167(11) -0.0021(9) -0.0026(9) 0.0030(9) C2 0.0189(11) 0.0267(13) 0.0196(12) 0.0017(10) -0.0019(9) -0.0011(10) C3 0.0173(11) 0.0209(12) 0.0228(12) 0.0013(10) -0.0044(9) -0.0001(9) C4 0.0157(11) 0.0240(13) 0.0213(12) -0.0025(10) -0.0029(9) 0.0021(9) C5 0.0171(11) 0.0245(13) 0.0196(12) 0.0026(10) -0.0014(9) 0.0015(9) C6 0.0213(12) 0.0207(12) 0.0224(12) 0.0011(10) -0.0021(10) 0.0012(9) C7 0.0282(13) 0.0273(13) 0.0230(12) -0.0033(10) 0.0009(10) 0.0036(11) C8 0.0403(16) 0.0455(18) 0.0311(15) -0.0065(13) 0.0111(13) -0.0156(13) C9 0.0223(12) 0.0236(13) 0.0275(13) 0.0018(10) -0.0054(10) -0.0008(10) C10 0.0289(13) 0.0325(15) 0.0304(14) -0.0104(12) 0.0048(11) -0.0026(11) C11 0.0243(12) 0.0293(14) 0.0212(12) 0.0035(10) 0.0021(10) -0.0001(10) C12 0.0398(15) 0.0239(14) 0.0401(16) -0.0030(12) 0.0106(13) -0.0059(12) C13 0.0215(12) 0.0322(14) 0.0261(13) -0.0070(11) 0.0018(10) -0.0045(11) C14 0.0217(12) 0.0332(15) 0.0361(15) -0.0150(12) -0.0028(11) 0.0017(11) C15 0.0273(13) 0.0228(13) 0.0393(16) -0.0061(11) -0.0126(12) 0.0005(11) C16 0.0240(12) 0.0236(13) 0.0310(14) -0.0015(11) -0.0082(10) -0.0035(10) C17 0.0376(15) 0.0228(14) 0.0388(16) 0.0086(12) -0.0096(12) -0.0073(11) C18 0.0329(14) 0.0337(15) 0.0311(14) 0.0113(12) -0.0025(12) -0.0116(12) C19 0.0219(12) 0.0329(14) 0.0228(12) 0.0037(11) -0.0014(10) -0.0067(11) C20 0.0228(12) 0.0477(17) 0.0219(13) 0.0055(12) 0.0034(10) -0.0065(12) C21 0.0235(13) 0.0441(17) 0.0240(13) -0.0028(12) 0.0035(10) 0.0057(12) C22 0.0235(12) 0.0283(14) 0.0223(12) 0.0002(10) -0.0015(10) 0.0060(10) C23 0.0188(11) 0.0250(13) 0.0198(12) 0.0017(10) -0.0033(9) -0.0028(10) C24 0.0189(11) 0.0222(12) 0.0232(12) 0.0003(10) -0.0045(9) -0.0036(10) O1W 0.180(10) 0.144(7) 0.135(7) 0.000(5) -0.062(6) 0.011(6) O1W' 0.176(14) 0.257(18) 0.125(10) 0.060(10) 0.036(9) -0.031(12) _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 Cu1 O7 1.9310(18) . ? Cu1 O2 1.9713(17) 4_576 ? Cu1 N2 2.021(2) . ? Cu1 N1 2.038(2) . ? Cu1 O4 2.2628(17) 1_455 ? O1 P1 1.5458(19) . ? O1 H1A 0.8200 . ? O2 P1 1.4955(18) . ? O2 Cu1 1.9713(17) 4_675 ? O3 P1 1.5476(19) . ? O3 H3A 0.8200 . ? O4 P2 1.4945(17) . ? O4 Cu1 2.2628(17) 1_655 ? O5 P2 1.5713(17) . ? O5 H5A 0.8200 . ? O6 P2 1.5321(18) . ? O7 P3 1.4948(18) . ? O8 P3 1.5751(18) . ? O8 H8D 0.8200 . ? O9 P3 1.5120(18) . ? N1 C22 1.330(3) . ? N1 C23 1.361(3) . ? N2 C13 1.329(3) . ? N2 C24 1.357(3) . ? P1 C7 1.805(3) . ? P2 C9 1.826(2) . ? P3 C11 1.812(2) . ? C1 C2 1.398(3) . ? C1 C6 1.403(3) . ? C1 C7 1.524(3) . ? C2 C3 1.405(3) . ? C2 C8 1.511(3) . ? C3 C4 1.400(3) . ? C3 C9 1.525(3) . ? C4 C5 1.405(3) . ? C4 C10 1.519(3) . ? C5 C6 1.410(3) . ? C5 C11 1.517(3) . ? C6 C12 1.515(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.390(4) . ? C13 H13A 0.9300 . ? C14 C15 1.370(4) . ? C14 H14A 0.9300 . ? C15 C16 1.403(4) . ? C15 H15A 0.9300 . ? C16 C24 1.402(3) . ? C16 C17 1.430(4) . ? C17 C18 1.352(4) . ? C17 H17A 0.9300 . ? C18 C19 1.432(4) . ? C18 H18A 0.9300 . ? C19 C23 1.404(3) . ? C19 C20 1.408(4) . ? C20 C21 1.363(4) . ? C20 H20A 0.9300 . ? C21 C22 1.401(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.429(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 O7 Cu1 O2 96.57(8) . 4_576 ? O7 Cu1 N2 169.21(8) . . ? O2 Cu1 N2 89.94(8) 4_576 . ? O7 Cu1 N1 88.79(8) . . ? O2 Cu1 N1 148.16(8) 4_576 . ? N2 Cu1 N1 81.19(8) . . ? O7 Cu1 O4 92.47(7) . 1_455 ? O2 Cu1 O4 100.73(7) 4_576 1_455 ? N2 Cu1 O4 94.77(7) . 1_455 ? N1 Cu1 O4 110.40(7) . 1_455 ? P1 O1 H1A 109.5 . . ? P1 O2 Cu1 142.78(12) . 4_675 ? P1 O3 H3A 109.5 . . ? P2 O4 Cu1 126.06(10) . 1_655 ? P2 O5 H5A 109.5 . . ? P3 O7 Cu1 147.24(12) . . ? P3 O8 H8D 109.5 . . ? C22 N1 C23 118.2(2) . . ? C22 N1 Cu1 129.38(17) . . ? C23 N1 Cu1 112.39(15) . . ? C13 N2 C24 117.7(2) . . ? C13 N2 Cu1 128.88(17) . . ? C24 N2 Cu1 112.89(16) . . ? O2 P1 O1 114.38(11) . . ? O2 P1 O3 112.66(10) . . ? O1 P1 O3 107.02(11) . . ? O2 P1 C7 107.85(11) . . ? O1 P1 C7 106.18(12) . . ? O3 P1 C7 108.44(11) . . ? O4 P2 O6 115.40(10) . . ? O4 P2 O5 107.90(10) . . ? O6 P2 O5 109.18(10) . . ? O4 P2 C9 113.94(11) . . ? O6 P2 C9 107.86(11) . . ? O5 P2 C9 101.60(10) . . ? O7 P3 O9 116.86(10) . . ? O7 P3 O8 106.87(11) . . ? O9 P3 O8 109.23(10) . . ? O7 P3 C11 110.37(11) . . ? O9 P3 C11 105.93(11) . . ? O8 P3 C11 107.24(11) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 C7 119.5(2) . . ? C6 C1 C7 119.7(2) . . ? C1 C2 C3 119.5(2) . . ? C1 C2 C8 121.5(2) . . ? C3 C2 C8 119.0(2) . . ? C4 C3 C2 120.5(2) . . ? C4 C3 C9 120.8(2) . . ? C2 C3 C9 118.6(2) . . ? C3 C4 C5 119.6(2) . . ? C3 C4 C10 119.4(2) . . ? C5 C4 C10 121.0(2) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 C11 119.9(2) . . ? C6 C5 C11 119.8(2) . . ? C1 C6 C5 119.2(2) . . ? C1 C6 C12 119.7(2) . . ? C5 C6 C12 121.1(2) . . ? C1 C7 P1 116.68(17) . . ? C1 C7 H7A 108.1 . . ? P1 C7 H7A 108.1 . . ? C1 C7 H7B 108.1 . . ? P1 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 P2 121.36(17) . . ? C3 C9 H9A 107.0 . . ? P2 C9 H9A 107.0 . . ? C3 C9 H9B 107.0 . . ? P2 C9 H9B 107.0 . . ? H9A C9 H9B 106.7 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 P3 116.95(17) . . ? C5 C11 H11A 108.1 . . ? P3 C11 H11A 108.1 . . ? C5 C11 H11B 108.1 . . ? P3 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 122.7(2) . . ? N2 C13 H13A 118.7 . . ? C14 C13 H13A 118.7 . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C24 C16 C15 116.8(2) . . ? C24 C16 C17 118.6(2) . . ? C15 C16 C17 124.6(2) . . ? C18 C17 C16 121.2(2) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C17 C18 C19 121.4(2) . . ? C17 C18 H18A 119.3 . . ? C19 C18 H18A 119.3 . . ? C23 C19 C20 116.6(2) . . ? C23 C19 C18 118.3(2) . . ? C20 C19 C18 125.0(2) . . ? C21 C20 C19 119.8(2) . . ? C21 C20 H20A 120.1 . . ? C19 C20 H20A 120.1 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? N1 C22 C21 122.0(2) . . ? N1 C22 H22A 119.0 . . ? C21 C22 H22A 119.0 . . ? N1 C23 C19 123.3(2) . . ? N1 C23 C24 116.4(2) . . ? C19 C23 C24 120.2(2) . . ? N2 C24 C16 123.5(2) . . ? N2 C24 C23 116.4(2) . . ? C16 C24 C23 120.1(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O6 0.82 1.76 2.551(2) 160.6 4_575 O3 H3A O9 0.82 1.71 2.525(2) 170.0 4_675 O5 H5A O9 0.82 1.75 2.549(2) 165.2 2_755 O8 H8D O6 0.82 1.92 2.723(3) 166.9 2_745 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.460 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.064 data_7 _database_code_depnum_ccdc_archive 'CCDC 900080' #TrackingRef '7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 Cu N2 O11 P3' _chemical_formula_weight 655.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 '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 8.7633(6) _cell_length_b 10.5590(7) _cell_length_c 14.8583(10) _cell_angle_alpha 79.7070(10) _cell_angle_beta 86.7760(10) _cell_angle_gamma 67.1110(10) _cell_volume 1246.09(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3966 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25 _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 678 _exptl_absorpt_coefficient_mu 1.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6383 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4334 _reflns_number_gt 3576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0584P)^2^+1.3082P] 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 4334 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.25798(5) -0.09170(4) 0.60000(3) 0.01587(14) Uani 1 1 d . . . O1W O 0.3726(5) 0.0798(4) 0.5588(2) 0.0509(9) Uani 1 1 d . . . H1W H 0.2846 0.1548 0.5731 0.057(18) Uiso 1 1 d R . . O1 O 0.1370(3) 0.3346(2) -0.03262(16) 0.0187(5) Uani 1 1 d . . . O2 O -0.0350(3) 0.3026(2) -0.15226(17) 0.0214(5) Uani 1 1 d . . . O3 O -0.1577(3) 0.5065(2) -0.07170(16) 0.0208(5) Uani 1 1 d . . . H3A H -0.1345 0.5432 -0.0332 0.031 Uiso 1 1 calc R . . O4 O 0.2228(3) -0.1734(2) 0.32428(17) 0.0225(6) Uani 1 1 d . . . H4A H 0.3216 -0.1888 0.3174 0.034 Uiso 1 1 calc R . . O5 O -0.0337(3) -0.0383(2) 0.39463(17) 0.0230(6) Uani 1 1 d . . . O6 O 0.2433(3) -0.1115(3) 0.47572(17) 0.0293(6) Uani 1 1 d . . . O7 O -0.1579(3) 0.6729(2) 0.27401(17) 0.0238(6) Uani 1 1 d . . . H7C H -0.1112 0.6850 0.2258 0.036 Uiso 1 1 calc R . . O8 O -0.3765(3) 0.7485(2) 0.14919(18) 0.0237(6) Uani 1 1 d . . . H8D H -0.2927 0.7156 0.1197 0.036 Uiso 1 1 calc R . . O9 O -0.4627(3) 0.7892(2) 0.30818(19) 0.0275(6) Uani 1 1 d . . . N1 N 0.3113(3) -0.0954(3) 0.72970(19) 0.0156(6) Uani 1 1 d . . . N2 N 0.4712(3) -0.2576(3) 0.61449(19) 0.0154(6) Uani 1 1 d . . . P1 P -0.03417(11) 0.35070(9) -0.06240(6) 0.0175(2) Uani 1 1 d . . . P2 P 0.14595(11) -0.06073(9) 0.38755(6) 0.0158(2) Uani 1 1 d . . . P3 P -0.33613(11) 0.69309(9) 0.25375(7) 0.0208(2) Uani 1 1 d . . . C1 C -0.1061(4) 0.2722(3) 0.1203(2) 0.0185(7) Uani 1 1 d . . . C2 C 0.0312(4) 0.1804(3) 0.1759(2) 0.0169(7) Uani 1 1 d . . . C3 C 0.0405(4) 0.1996(3) 0.2662(2) 0.0164(7) Uani 1 1 d . . . C4 C -0.0802(4) 0.3139(3) 0.2991(2) 0.0203(8) Uani 1 1 d . . . C5 C -0.2178(4) 0.4043(3) 0.2436(2) 0.0194(8) Uani 1 1 d . . . C6 C -0.2331(4) 0.3808(3) 0.1549(2) 0.0185(8) Uani 1 1 d . . . C7 C -0.1160(4) 0.2499(4) 0.0226(2) 0.0193(8) Uani 1 1 d . . . H7A H -0.2311 0.2733 0.0073 0.023 Uiso 1 1 calc R . . H7B H -0.0561 0.1518 0.0198 0.023 Uiso 1 1 calc R . . C8 C 0.1639(5) 0.0612(3) 0.1380(2) 0.0217(8) Uani 1 1 d . . . H8A H 0.1371 0.0647 0.0756 0.033 Uiso 1 1 calc R . . H8B H 0.1699 -0.0259 0.1737 0.033 Uiso 1 1 calc R . . H8C H 0.2689 0.0693 0.1407 0.033 Uiso 1 1 calc R . . C9 C 0.1772(4) 0.0948(3) 0.3309(2) 0.0196(8) Uani 1 1 d . . . H9A H 0.1929 0.1421 0.3776 0.024 Uiso 1 1 calc R . . H9B H 0.2791 0.0655 0.2967 0.024 Uiso 1 1 calc R . . C10 C -0.0657(5) 0.3415(4) 0.3940(3) 0.0290(9) Uani 1 1 d . . . H10A H 0.0329 0.2710 0.4237 0.044 Uiso 1 1 calc R . . H10B H -0.1606 0.3396 0.4289 0.044 Uiso 1 1 calc R . . H10C H -0.0602 0.4314 0.3897 0.044 Uiso 1 1 calc R . . C11 C -0.3515(5) 0.5243(3) 0.2808(3) 0.0238(8) Uani 1 1 d . . . H11A H -0.3513 0.4990 0.3469 0.029 Uiso 1 1 calc R . . H11B H -0.4578 0.5339 0.2582 0.029 Uiso 1 1 calc R . . C12 C -0.3880(4) 0.4687(4) 0.0977(3) 0.0236(8) Uani 1 1 d . . . H12A H -0.4621 0.5379 0.1308 0.035 Uiso 1 1 calc R . . H12B H -0.4415 0.4100 0.0845 0.035 Uiso 1 1 calc R . . H12C H -0.3586 0.5138 0.0414 0.035 Uiso 1 1 calc R . . C13 C 0.5382(4) -0.3417(4) 0.5531(2) 0.0219(8) Uani 1 1 d . . . H13A H 0.4867 -0.3193 0.4961 0.026 Uiso 1 1 calc R . . C14 C 0.6806(5) -0.4602(4) 0.5712(3) 0.0256(8) Uani 1 1 d . . . H14A H 0.7224 -0.5179 0.5276 0.031 Uiso 1 1 calc R . . C15 C 0.7608(5) -0.4924(4) 0.6547(3) 0.0271(9) Uani 1 1 d . . . H15A H 0.8566 -0.5723 0.6682 0.032 Uiso 1 1 calc R . . C16 C 0.6958(4) -0.4036(4) 0.7180(2) 0.0206(8) Uani 1 1 d . . . H16A H 0.7492 -0.4212 0.7739 0.025 Uiso 1 1 calc R . . C17 C 0.5496(4) -0.2882(3) 0.6960(2) 0.0153(7) Uani 1 1 d . . . C18 C 0.4615(4) -0.1915(3) 0.7602(2) 0.0143(7) Uani 1 1 d . . . C19 C 0.5239(5) -0.1976(4) 0.8453(2) 0.0212(8) Uani 1 1 d . . . H19A H 0.6287 -0.2624 0.8646 0.025 Uiso 1 1 calc R . . C20 C 0.4281(5) -0.1064(4) 0.9006(3) 0.0250(9) Uani 1 1 d . . . H20A H 0.4671 -0.1091 0.9581 0.030 Uiso 1 1 calc R . . C21 C 0.2729(5) -0.0104(4) 0.8701(3) 0.0226(8) Uani 1 1 d . . . H21A H 0.2056 0.0510 0.9071 0.027 Uiso 1 1 calc R . . C22 C 0.2201(4) -0.0072(3) 0.7842(2) 0.0193(8) Uani 1 1 d . . . H22A H 0.1169 0.0589 0.7632 0.023 Uiso 1 1 calc R . . O2W O 0.092(2) 0.2942(17) 0.5713(12) 0.020(6) Uiso 0.134(9) 1 d P . . 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 Cu1 0.0121(2) 0.0156(2) 0.0160(2) 0.00034(16) -0.00241(16) -0.00211(17) O1W 0.065(2) 0.066(2) 0.0368(19) 0.0133(16) -0.0039(17) -0.051(2) O1 0.0146(12) 0.0192(12) 0.0214(13) -0.0033(10) 0.0007(10) -0.0057(10) O2 0.0197(13) 0.0235(13) 0.0225(14) -0.0044(10) 0.0031(11) -0.0102(11) O3 0.0195(13) 0.0181(12) 0.0204(13) 0.0001(10) -0.0053(10) -0.0030(11) O4 0.0196(13) 0.0192(13) 0.0259(14) -0.0076(11) 0.0066(11) -0.0039(11) O5 0.0122(13) 0.0221(13) 0.0269(15) 0.0029(11) -0.0022(11) -0.0009(11) O6 0.0193(14) 0.0419(16) 0.0142(14) -0.0015(11) -0.0032(11) 0.0005(12) O7 0.0192(13) 0.0231(13) 0.0278(15) -0.0048(11) 0.0083(11) -0.0078(11) O8 0.0177(13) 0.0180(13) 0.0309(15) -0.0023(11) 0.0021(11) -0.0029(11) O9 0.0221(14) 0.0202(13) 0.0388(16) -0.0118(12) 0.0110(12) -0.0052(11) N1 0.0135(15) 0.0150(14) 0.0185(16) -0.0008(12) 0.0010(12) -0.0065(12) N2 0.0144(15) 0.0167(14) 0.0141(15) 0.0008(11) -0.0007(12) -0.0062(12) P1 0.0153(5) 0.0177(5) 0.0177(5) 0.0006(4) 0.0001(4) -0.0059(4) P2 0.0121(5) 0.0171(4) 0.0126(5) -0.0003(3) -0.0006(3) -0.0003(4) P3 0.0162(5) 0.0143(5) 0.0295(6) -0.0054(4) 0.0073(4) -0.0036(4) C1 0.0209(19) 0.0154(17) 0.0202(19) 0.0002(14) 0.0026(15) -0.0099(15) C2 0.0172(18) 0.0123(16) 0.0216(19) -0.0013(14) 0.0031(14) -0.0072(14) C3 0.0169(18) 0.0146(17) 0.0192(19) -0.0015(14) 0.0036(14) -0.0086(15) C4 0.023(2) 0.0153(17) 0.026(2) -0.0037(15) 0.0039(16) -0.0105(16) C5 0.0191(19) 0.0131(17) 0.026(2) -0.0025(14) 0.0082(15) -0.0081(15) C6 0.0117(17) 0.0130(16) 0.029(2) 0.0038(14) 0.0022(15) -0.0058(14) C7 0.0207(19) 0.0203(18) 0.0176(19) 0.0014(14) -0.0001(15) -0.0108(16) C8 0.023(2) 0.0170(18) 0.022(2) -0.0023(15) 0.0018(15) -0.0044(16) C9 0.0189(19) 0.0182(18) 0.0215(19) -0.0044(14) -0.0007(15) -0.0063(15) C10 0.034(2) 0.027(2) 0.024(2) -0.0092(17) 0.0023(18) -0.0082(18) C11 0.022(2) 0.0159(18) 0.031(2) -0.0036(15) 0.0078(16) -0.0065(16) C12 0.0174(19) 0.0216(19) 0.026(2) 0.0020(15) -0.0002(16) -0.0043(16) C13 0.0200(19) 0.026(2) 0.0180(19) -0.0040(15) 0.0004(15) -0.0067(16) C14 0.023(2) 0.024(2) 0.023(2) -0.0085(16) 0.0040(16) -0.0008(17) C15 0.0164(19) 0.023(2) 0.032(2) -0.0027(17) -0.0001(16) 0.0014(16) C16 0.0136(18) 0.0241(19) 0.0208(19) -0.0021(15) -0.0025(15) -0.0043(15) C17 0.0114(17) 0.0157(17) 0.0171(18) 0.0015(13) -0.0002(14) -0.0051(14) C18 0.0144(17) 0.0135(16) 0.0160(17) 0.0005(13) 0.0008(14) -0.0079(14) C19 0.023(2) 0.0174(18) 0.022(2) 0.0005(15) -0.0052(15) -0.0078(16) C20 0.038(2) 0.026(2) 0.0172(19) -0.0052(15) -0.0035(17) -0.0184(18) C21 0.029(2) 0.0161(18) 0.025(2) -0.0073(15) 0.0073(16) -0.0105(16) C22 0.0194(19) 0.0142(17) 0.024(2) -0.0015(14) 0.0029(15) -0.0068(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O6 1.912(3) . ? Cu1 O5 1.917(2) 2_556 ? Cu1 N2 1.992(3) . ? Cu1 N1 1.999(3) . ? Cu1 O1W 2.368(3) . ? O1W H1W 0.9130 . ? O1 P1 1.524(2) . ? O2 P1 1.512(3) . ? O3 P1 1.564(2) . ? O3 H3A 0.8200 . ? O4 P2 1.568(2) . ? O4 H4A 0.8200 . ? O5 P2 1.499(2) . ? O5 Cu1 1.917(2) 2_556 ? O6 P2 1.500(3) . ? O7 P3 1.532(3) . ? O7 H7C 0.8200 . ? O8 P3 1.567(3) . ? O8 H8D 0.8200 . ? O9 P3 1.494(3) . ? N1 C22 1.334(4) . ? N1 C18 1.353(4) . ? N2 C13 1.337(4) . ? N2 C17 1.351(4) . ? P1 C7 1.804(3) . ? P2 C9 1.819(3) . ? P3 C11 1.812(3) . ? C1 C6 1.404(5) . ? C1 C2 1.410(5) . ? C1 C7 1.525(5) . ? C2 C3 1.403(5) . ? C2 C8 1.514(5) . ? C3 C4 1.406(5) . ? C3 C9 1.517(5) . ? C4 C5 1.407(5) . ? C4 C10 1.511(5) . ? C5 C6 1.406(5) . ? C5 C11 1.518(5) . ? C6 C12 1.515(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.378(5) . ? C13 H13A 0.9300 . ? C14 C15 1.382(5) . ? C14 H14A 0.9300 . ? C15 C16 1.389(5) . ? C15 H15A 0.9300 . ? C16 C17 1.387(5) . ? C16 H16A 0.9300 . ? C17 C18 1.483(5) . ? C18 C19 1.387(5) . ? C19 C20 1.372(5) . ? C19 H19A 0.9300 . ? C20 C21 1.384(5) . ? C20 H20A 0.9300 . ? C21 C22 1.372(5) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? 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 O6 Cu1 O5 95.37(11) . 2_556 ? O6 Cu1 N2 89.42(11) . . ? O5 Cu1 N2 166.22(11) 2_556 . ? O6 Cu1 N1 170.45(11) . . ? O5 Cu1 N1 94.16(11) 2_556 . ? N2 Cu1 N1 81.14(11) . . ? O6 Cu1 O1W 92.85(12) . . ? O5 Cu1 O1W 95.53(12) 2_556 . ? N2 Cu1 O1W 97.13(13) . . ? N1 Cu1 O1W 86.93(11) . . ? Cu1 O1W H1W 98.5 . . ? P1 O3 H3A 109.5 . . ? P2 O4 H4A 109.5 . . ? P2 O5 Cu1 147.27(16) . 2_556 ? P2 O6 Cu1 147.88(17) . . ? P3 O7 H7C 109.5 . . ? P3 O8 H8D 109.5 . . ? C22 N1 C18 118.8(3) . . ? C22 N1 Cu1 126.4(2) . . ? C18 N1 Cu1 114.6(2) . . ? C13 N2 C17 118.4(3) . . ? C13 N2 Cu1 126.2(2) . . ? C17 N2 Cu1 115.3(2) . . ? O2 P1 O1 113.62(14) . . ? O2 P1 O3 108.03(14) . . ? O1 P1 O3 110.56(13) . . ? O2 P1 C7 107.11(15) . . ? O1 P1 C7 110.08(15) . . ? O3 P1 C7 107.17(15) . . ? O5 P2 O6 116.15(15) . . ? O5 P2 O4 105.45(14) . . ? O6 P2 O4 108.28(14) . . ? O5 P2 C9 112.39(15) . . ? O6 P2 C9 107.45(16) . . ? O4 P2 C9 106.66(15) . . ? O9 P3 O7 113.74(15) . . ? O9 P3 O8 109.43(15) . . ? O7 P3 O8 109.77(14) . . ? O9 P3 C11 107.95(16) . . ? O7 P3 C11 108.03(16) . . ? O8 P3 C11 107.72(16) . . ? C6 C1 C2 120.6(3) . . ? C6 C1 C7 120.5(3) . . ? C2 C1 C7 118.9(3) . . ? C3 C2 C1 119.2(3) . . ? C3 C2 C8 121.2(3) . . ? C1 C2 C8 119.6(3) . . ? C2 C3 C4 120.5(3) . . ? C2 C3 C9 120.7(3) . . ? C4 C3 C9 118.8(3) . . ? C3 C4 C5 119.9(3) . . ? C3 C4 C10 121.1(3) . . ? C5 C4 C10 119.0(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 C11 120.4(3) . . ? C4 C5 C11 119.8(3) . . ? C1 C6 C5 119.7(3) . . ? C1 C6 C12 119.7(3) . . ? C5 C6 C12 120.5(3) . . ? C1 C7 P1 114.6(2) . . ? C1 C7 H7A 108.6 . . ? P1 C7 H7A 108.6 . . ? C1 C7 H7B 108.6 . . ? P1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 P2 116.8(2) . . ? C3 C9 H9A 108.1 . . ? P2 C9 H9A 108.1 . . ? C3 C9 H9B 108.1 . . ? P2 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 P3 117.0(2) . . ? C5 C11 H11A 108.1 . . ? P3 C11 H11A 108.1 . . ? C5 C11 H11B 108.1 . . ? P3 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 122.5(3) . . ? N2 C13 H13A 118.8 . . ? C14 C13 H13A 118.8 . . ? C13 C14 C15 119.3(3) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 H15A 120.5 . . ? C16 C15 H15A 120.5 . . ? C17 C16 C15 118.5(3) . . ? C17 C16 H16A 120.7 . . ? C15 C16 H16A 120.7 . . ? N2 C17 C16 122.3(3) . . ? N2 C17 C18 114.0(3) . . ? C16 C17 C18 123.7(3) . . ? N1 C18 C19 121.5(3) . . ? N1 C18 C17 114.5(3) . . ? C19 C18 C17 124.0(3) . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C19 C20 C21 119.5(3) . . ? C19 C20 H20A 120.3 . . ? C21 C20 H20A 120.3 . . ? C22 C21 C20 118.9(3) . . ? C22 C21 H21A 120.6 . . ? C20 C21 H21A 120.6 . . ? N1 C22 C21 122.4(3) . . ? N1 C22 H22A 118.8 . . ? C21 C22 H22A 118.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O6 P2 10.3(4) 2_556 . . . ? N2 Cu1 O6 P2 177.4(4) . . . . ? N1 Cu1 O6 P2 -173.9(5) . . . . ? O1W Cu1 O6 P2 -85.5(4) . . . . ? O6 Cu1 N1 C22 171.6(6) . . . . ? O5 Cu1 N1 C22 -12.6(3) 2_556 . . . ? N2 Cu1 N1 C22 -179.6(3) . . . . ? O1W Cu1 N1 C22 82.7(3) . . . . ? O6 Cu1 N1 C18 -3.0(8) . . . . ? O5 Cu1 N1 C18 172.8(2) 2_556 . . . ? N2 Cu1 N1 C18 5.8(2) . . . . ? O1W Cu1 N1 C18 -91.9(2) . . . . ? O6 Cu1 N2 C13 -7.0(3) . . . . ? O5 Cu1 N2 C13 103.6(5) 2_556 . . . ? N1 Cu1 N2 C13 174.5(3) . . . . ? O1W Cu1 N2 C13 -99.8(3) . . . . ? O6 Cu1 N2 C17 175.6(2) . . . . ? O5 Cu1 N2 C17 -73.9(5) 2_556 . . . ? N1 Cu1 N2 C17 -3.0(2) . . . . ? O1W Cu1 N2 C17 82.7(2) . . . . ? Cu1 O5 P2 O6 98.4(3) 2_556 . . . ? Cu1 O5 P2 O4 -141.7(3) 2_556 . . . ? Cu1 O5 P2 C9 -25.9(4) 2_556 . . . ? Cu1 O6 P2 O5 -48.1(4) . . . . ? Cu1 O6 P2 O4 -166.4(3) . . . . ? Cu1 O6 P2 C9 78.7(4) . . . . ? C6 C1 C2 C3 -0.6(5) . . . . ? C7 C1 C2 C3 -179.5(3) . . . . ? C6 C1 C2 C8 178.1(3) . . . . ? C7 C1 C2 C8 -0.8(5) . . . . ? C1 C2 C3 C4 -3.9(5) . . . . ? C8 C2 C3 C4 177.4(3) . . . . ? C1 C2 C3 C9 173.9(3) . . . . ? C8 C2 C3 C9 -4.8(5) . . . . ? C2 C3 C4 C5 4.6(5) . . . . ? C9 C3 C4 C5 -173.3(3) . . . . ? C2 C3 C4 C10 -175.8(3) . . . . ? C9 C3 C4 C10 6.3(5) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C10 C4 C5 C6 179.7(3) . . . . ? C3 C4 C5 C11 177.5(3) . . . . ? C10 C4 C5 C11 -2.1(5) . . . . ? C2 C1 C6 C5 4.5(5) . . . . ? C7 C1 C6 C5 -176.7(3) . . . . ? C2 C1 C6 C12 -173.5(3) . . . . ? C7 C1 C6 C12 5.4(5) . . . . ? C4 C5 C6 C1 -3.8(5) . . . . ? C11 C5 C6 C1 178.0(3) . . . . ? C4 C5 C6 C12 174.2(3) . . . . ? C11 C5 C6 C12 -4.0(5) . . . . ? C6 C1 C7 P1 86.9(4) . . . . ? C2 C1 C7 P1 -94.2(3) . . . . ? O2 P1 C7 C1 173.2(2) . . . . ? O1 P1 C7 C1 49.3(3) . . . . ? O3 P1 C7 C1 -71.0(3) . . . . ? C2 C3 C9 P2 -82.2(4) . . . . ? C4 C3 C9 P2 95.7(3) . . . . ? O5 P2 C9 C3 -24.5(3) . . . . ? O6 P2 C9 C3 -153.5(3) . . . . ? O4 P2 C9 C3 90.6(3) . . . . ? C6 C5 C11 P3 -85.9(4) . . . . ? C4 C5 C11 P3 95.9(4) . . . . ? O9 P3 C11 C5 -171.5(3) . . . . ? O7 P3 C11 C5 -48.1(3) . . . . ? O8 P3 C11 C5 70.5(3) . . . . ? C17 N2 C13 C14 2.1(5) . . . . ? Cu1 N2 C13 C14 -175.3(3) . . . . ? N2 C13 C14 C15 -1.8(6) . . . . ? C13 C14 C15 C16 -0.4(6) . . . . ? C14 C15 C16 C17 2.1(5) . . . . ? C13 N2 C17 C16 -0.3(5) . . . . ? Cu1 N2 C17 C16 177.4(3) . . . . ? C13 N2 C17 C18 -177.7(3) . . . . ? Cu1 N2 C17 C18 -0.1(3) . . . . ? C15 C16 C17 N2 -1.8(5) . . . . ? C15 C16 C17 C18 175.4(3) . . . . ? C22 N1 C18 C19 -1.8(5) . . . . ? Cu1 N1 C18 C19 173.3(2) . . . . ? C22 N1 C18 C17 177.5(3) . . . . ? Cu1 N1 C18 C17 -7.4(3) . . . . ? N2 C17 C18 N1 5.0(4) . . . . ? C16 C17 C18 N1 -172.5(3) . . . . ? N2 C17 C18 C19 -175.8(3) . . . . ? C16 C17 C18 C19 6.8(5) . . . . ? N1 C18 C19 C20 2.0(5) . . . . ? C17 C18 C19 C20 -177.2(3) . . . . ? C18 C19 C20 C21 -0.4(5) . . . . ? C19 C20 C21 C22 -1.3(5) . . . . ? C18 N1 C22 C21 0.0(5) . . . . ? Cu1 N1 C22 C21 -174.5(2) . . . . ? C20 C21 C22 N1 1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.679 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.085 data_8 _database_code_depnum_ccdc_archive 'CCDC 900081' #TrackingRef '8.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H24.20 Mn1.50 O12.10 P3' _chemical_formula_weight 537.43 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' 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' Mn Mn 0.3368 0.7283 '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 8.3270(4) _cell_length_b 9.9585(5) _cell_length_c 13.2645(7) _cell_angle_alpha 68.0340(10) _cell_angle_beta 82.3390(10) _cell_angle_gamma 72.1690(10) _cell_volume 970.88(8) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3639 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25 _exptl_crystal_description Octahedron _exptl_crystal_colour Pink _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 551 _exptl_absorpt_coefficient_mu 1.299 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_correction_T_max 0.771 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4976 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3372 _reflns_number_gt 3054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0464P)^2^+1.4799P] 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 3372 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Mn1 Mn 1.02645(5) 0.14617(5) 0.38823(3) 0.01235(14) Uani 1 1 d . . . Mn2 Mn 0.5000 0.0000 0.5000 0.01220(16) Uani 1 2 d S . . O1 O 0.4775(2) 0.2215(2) 0.37171(17) 0.0159(5) Uani 1 1 d . . . O1W O 0.3040(3) -0.0224(2) 0.40766(18) 0.0198(5) Uani 1 1 d . . . H1W H 0.2806 -0.1027 0.4498 0.024 Uiso 1 1 d R . . H2W H 0.3465 -0.0189 0.3451 0.024 Uiso 1 1 d R . . O2W O 1.1386(3) 0.3305(2) 0.35358(18) 0.0190(5) Uani 1 1 d . . . H3W H 1.1240 0.3789 0.2859 0.023 Uiso 1 1 d R . . H4W H 1.2448 0.3052 0.3607 0.023 Uiso 1 1 d R . . O2 O 0.6322(3) 0.2992(2) 0.19697(17) 0.0182(5) Uani 1 1 d . . . H2A H 0.7171 0.3247 0.1688 0.027 Uiso 1 1 calc R . . O3 O 0.7663(3) 0.2509(2) 0.37560(17) 0.0170(5) Uani 1 1 d . . . O3W O 0.4873(4) 0.0101(4) 0.2161(2) 0.0589(9) Uani 1 1 d . . . H5W H 0.5643 -0.0689 0.2158 0.071 Uiso 1 1 d R . . H6W H 0.5663 0.0469 0.2175 0.071 Uiso 1 1 d R . . O4 O 0.6964(3) 0.8825(2) 0.42143(17) 0.0167(5) Uani 1 1 d . . . O4W O 0.335(4) -0.124(3) 0.2593(19) 0.038(7) Uani 0.10 1 d P . . H8W H 0.3262 -0.1008 0.1913 0.045 Uiso 0.10 1 d PR . . H7W H 0.4043 -0.2089 0.2916 0.045 Uiso 0.10 1 d PR . . O5 O 0.8562(3) 0.9960(2) 0.25362(17) 0.0192(5) Uani 1 1 d . . . H5A H 0.9187 1.0492 0.2452 0.029 Uiso 1 1 calc R . . O6 O 0.9836(3) 0.9139(2) 0.43680(16) 0.0143(4) Uani 1 1 d . . . O7 O 0.8527(3) 0.6017(2) -0.11854(17) 0.0192(5) Uani 1 1 d . . . H7C H 0.8644 0.5283 -0.0620 0.029 Uiso 1 1 calc R . . O8 O 1.1130(3) 0.6326(2) -0.05924(17) 0.0179(5) Uani 1 1 d . . . O9 O 0.9468(3) 0.8315(2) -0.22194(16) 0.0170(5) Uani 1 1 d . . . P1 P 0.60455(9) 0.30728(8) 0.31460(6) 0.01237(18) Uani 1 1 d . . . P2 P 0.86942(9) 0.88007(8) 0.37286(6) 0.01123(18) Uani 1 1 d . . . P3 P 0.94104(10) 0.71542(9) -0.10856(6) 0.01431(19) Uani 1 1 d . . . C1 C 0.6380(4) 0.5974(3) 0.2462(2) 0.0135(6) Uani 1 1 d . . . C2 C 0.7369(4) 0.6095(3) 0.3191(2) 0.0129(6) Uani 1 1 d . . . C3 C 0.8682(4) 0.6787(3) 0.2779(2) 0.0122(6) Uani 1 1 d . . . C4 C 0.8994(4) 0.7345(3) 0.1653(2) 0.0145(6) Uani 1 1 d . . . C5 C 0.7889(4) 0.7342(3) 0.0939(2) 0.0140(6) Uani 1 1 d . . . C6 C 0.6581(4) 0.6648(3) 0.1338(2) 0.0140(6) Uani 1 1 d . . . C7 C 0.5109(4) 0.5061(3) 0.2930(2) 0.0139(6) Uani 1 1 d . . . H7A H 0.4178 0.5457 0.2437 0.017 Uiso 1 1 calc R . . H7B H 0.4660 0.5172 0.3617 0.017 Uiso 1 1 calc R . . C8 C 0.6972(4) 0.5531(4) 0.4393(2) 0.0197(7) Uani 1 1 d . . . H8A H 0.6046 0.5099 0.4522 0.030 Uiso 1 1 calc R . . H8B H 0.6672 0.6357 0.4654 0.030 Uiso 1 1 calc R . . H8C H 0.7945 0.4780 0.4768 0.030 Uiso 1 1 calc R . . C9 C 0.9685(4) 0.7008(3) 0.3558(2) 0.0131(6) Uani 1 1 d . . . H9A H 1.0826 0.6973 0.3274 0.016 Uiso 1 1 calc R . . H9B H 0.9745 0.6199 0.4258 0.016 Uiso 1 1 calc R . . C10 C 1.0476(4) 0.7986(4) 0.1201(3) 0.0235(7) Uani 1 1 d . . . H10A H 1.1100 0.7905 0.1790 0.035 Uiso 1 1 calc R . . H10B H 1.0072 0.9027 0.0751 0.035 Uiso 1 1 calc R . . H10C H 1.1197 0.7433 0.0776 0.035 Uiso 1 1 calc R . . C11 C 0.8059(4) 0.8176(3) -0.0274(2) 0.0167(6) Uani 1 1 d . . . H11A H 0.8462 0.9032 -0.0366 0.020 Uiso 1 1 calc R . . H11B H 0.6938 0.8576 -0.0574 0.020 Uiso 1 1 calc R . . C12 C 0.5360(4) 0.6697(4) 0.0563(2) 0.0193(7) Uani 1 1 d . . . H12A H 0.4552 0.6175 0.0969 0.029 Uiso 1 1 calc R . . H12B H 0.5972 0.6221 0.0063 0.029 Uiso 1 1 calc R . . H12C H 0.4783 0.7728 0.0167 0.029 Uiso 1 1 calc R . . 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 Mn1 0.0136(2) 0.0153(2) 0.0095(2) -0.00376(19) 0.00009(17) -0.00668(18) Mn2 0.0114(3) 0.0130(3) 0.0120(3) -0.0036(3) 0.0007(2) -0.0044(2) O1 0.0133(10) 0.0142(10) 0.0176(11) -0.0008(9) 0.0001(8) -0.0067(8) O1W 0.0187(11) 0.0211(11) 0.0216(12) -0.0080(10) -0.0026(9) -0.0068(9) O2W 0.0164(11) 0.0195(11) 0.0213(12) -0.0046(9) -0.0037(9) -0.0073(9) O2 0.0189(11) 0.0233(11) 0.0159(11) -0.0085(9) 0.0031(9) -0.0100(9) O3 0.0141(10) 0.0178(11) 0.0197(12) -0.0062(9) -0.0015(9) -0.0057(9) O3W 0.0335(16) 0.098(3) 0.0400(18) -0.0281(18) -0.0119(13) -0.0023(17) O4 0.0153(11) 0.0192(11) 0.0190(11) -0.0108(9) 0.0037(9) -0.0062(9) O4W 0.071(19) 0.032(14) 0.010(12) -0.012(11) 0.001(12) -0.009(13) O5 0.0301(12) 0.0170(11) 0.0134(11) -0.0032(9) -0.0041(9) -0.0117(10) O6 0.0176(11) 0.0165(10) 0.0122(11) -0.0058(9) -0.0010(8) -0.0082(8) O7 0.0266(12) 0.0190(11) 0.0120(11) -0.0010(9) -0.0010(9) -0.0119(9) O8 0.0174(11) 0.0203(11) 0.0147(11) -0.0039(9) 0.0014(9) -0.0069(9) O9 0.0223(11) 0.0210(11) 0.0096(11) -0.0042(9) 0.0025(8) -0.0112(9) P1 0.0122(4) 0.0125(4) 0.0123(4) -0.0028(3) 0.0005(3) -0.0056(3) P2 0.0143(4) 0.0118(4) 0.0095(4) -0.0043(3) -0.0006(3) -0.0055(3) P3 0.0173(4) 0.0166(4) 0.0094(4) -0.0027(3) 0.0015(3) -0.0081(3) C1 0.0150(15) 0.0111(14) 0.0152(15) -0.0049(12) 0.0027(12) -0.0055(11) C2 0.0152(14) 0.0102(14) 0.0126(15) -0.0036(12) -0.0013(11) -0.0026(11) C3 0.0144(14) 0.0097(14) 0.0137(15) -0.0056(12) -0.0005(11) -0.0030(11) C4 0.0159(15) 0.0138(14) 0.0154(16) -0.0071(12) 0.0025(12) -0.0051(12) C5 0.0174(15) 0.0132(14) 0.0122(15) -0.0056(12) 0.0021(12) -0.0049(12) C6 0.0157(15) 0.0139(14) 0.0131(15) -0.0053(12) -0.0001(12) -0.0046(12) C7 0.0163(15) 0.0134(14) 0.0115(15) -0.0026(12) 0.0011(12) -0.0061(12) C8 0.0258(17) 0.0241(17) 0.0129(16) -0.0050(13) 0.0017(13) -0.0150(14) C9 0.0138(14) 0.0114(14) 0.0142(15) -0.0048(12) -0.0002(11) -0.0035(11) C10 0.0287(18) 0.038(2) 0.0143(16) -0.0124(15) 0.0069(13) -0.0232(16) C11 0.0198(16) 0.0180(15) 0.0132(16) -0.0050(13) 0.0029(12) -0.0086(13) C12 0.0210(16) 0.0248(17) 0.0127(16) -0.0031(13) -0.0008(12) -0.0116(13) _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 Mn1 O3 2.095(2) . ? Mn1 O9 2.120(2) 2_765 ? Mn1 O6 2.166(2) 2_766 ? Mn1 O2W 2.181(2) . ? Mn1 O6 2.285(2) 1_545 ? Mn1 O1W 2.384(2) 1_655 ? Mn2 O4 2.102(2) 1_545 ? Mn2 O4 2.102(2) 2_666 ? Mn2 O1 2.196(2) 2_656 ? Mn2 O1 2.196(2) . ? Mn2 O1W 2.275(2) 2_656 ? Mn2 O1W 2.275(2) . ? O1 P1 1.510(2) . ? O1W Mn1 2.384(2) 1_455 ? O2 P1 1.575(2) . ? O3 P1 1.507(2) . ? O4 P2 1.494(2) . ? O4 Mn2 2.102(2) 1_565 ? O5 P2 1.565(2) . ? O6 P2 1.537(2) . ? O6 Mn1 2.166(2) 2_766 ? O6 Mn1 2.285(2) 1_565 ? O7 P3 1.577(2) . ? O8 P3 1.510(2) . ? O9 P3 1.521(2) . ? O9 Mn1 2.120(2) 2_765 ? P1 C7 1.817(3) . ? P2 C9 1.808(3) . ? P3 C11 1.805(3) . ? C1 C6 1.398(4) . ? C1 C2 1.410(4) . ? C1 C7 1.525(4) . ? C2 C3 1.411(4) . ? C2 C8 1.506(4) . ? C3 C4 1.404(4) . ? C3 C9 1.525(4) . ? C4 C5 1.408(4) . ? C4 C10 1.513(4) . ? C5 C6 1.406(4) . ? C5 C11 1.520(4) . ? C6 C12 1.518(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O9 92.57(8) . 2_765 ? O3 Mn1 O6 92.36(8) . 2_766 ? O9 Mn1 O6 171.07(8) 2_765 2_766 ? O3 Mn1 O2W 104.37(8) . . ? O9 Mn1 O2W 90.27(8) 2_765 . ? O6 Mn1 O2W 95.71(8) 2_766 . ? O3 Mn1 O6 91.30(8) . 1_545 ? O9 Mn1 O6 91.32(8) 2_765 1_545 ? O6 Mn1 O6 81.13(8) 2_766 1_545 ? O2W Mn1 O6 164.17(8) . 1_545 ? O3 Mn1 O1W 167.05(8) . 1_655 ? O9 Mn1 O1W 86.04(8) 2_765 1_655 ? O6 Mn1 O1W 87.49(8) 2_766 1_655 ? O2W Mn1 O1W 88.52(8) . 1_655 ? O6 Mn1 O1W 75.88(7) 1_545 1_655 ? O4 Mn2 O4 180.0 1_545 2_666 ? O4 Mn2 O1 84.99(8) 1_545 2_656 ? O4 Mn2 O1 95.01(8) 2_666 2_656 ? O4 Mn2 O1 95.01(8) 1_545 . ? O4 Mn2 O1 84.99(8) 2_666 . ? O1 Mn2 O1 180.0 2_656 . ? O4 Mn2 O1W 89.09(8) 1_545 2_656 ? O4 Mn2 O1W 90.91(8) 2_666 2_656 ? O1 Mn2 O1W 86.09(8) 2_656 2_656 ? O1 Mn2 O1W 93.91(8) . 2_656 ? O4 Mn2 O1W 90.91(8) 1_545 . ? O4 Mn2 O1W 89.09(8) 2_666 . ? O1 Mn2 O1W 93.91(8) 2_656 . ? O1 Mn2 O1W 86.09(8) . . ? O1W Mn2 O1W 180.0 2_656 . ? P1 O1 Mn2 132.76(12) . . ? Mn2 O1W Mn1 120.08(9) . 1_455 ? P1 O3 Mn1 150.52(14) . . ? P2 O4 Mn2 142.09(13) . 1_565 ? P2 O6 Mn1 124.64(11) . 2_766 ? P2 O6 Mn1 122.63(11) . 1_565 ? Mn1 O6 Mn1 98.87(8) 2_766 1_565 ? P3 O9 Mn1 141.66(13) . 2_765 ? O3 P1 O1 113.27(12) . . ? O3 P1 O2 113.12(12) . . ? O1 P1 O2 106.41(12) . . ? O3 P1 C7 109.62(13) . . ? O1 P1 C7 109.28(13) . . ? O2 P1 C7 104.72(13) . . ? O4 P2 O6 114.40(12) . . ? O4 P2 O5 109.59(12) . . ? O6 P2 O5 108.88(11) . . ? O4 P2 C9 109.48(13) . . ? O6 P2 C9 110.51(13) . . ? O5 P2 C9 103.39(13) . . ? O8 P3 O9 113.32(12) . . ? O8 P3 O7 110.71(12) . . ? O9 P3 O7 106.84(12) . . ? O8 P3 C11 111.34(13) . . ? O9 P3 C11 105.95(13) . . ? O7 P3 C11 108.39(13) . . ? C6 C1 C2 121.0(3) . . ? C6 C1 C7 120.8(3) . . ? C2 C1 C7 118.3(3) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 C8 119.6(3) . . ? C3 C2 C8 121.0(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 C9 120.4(3) . . ? C2 C3 C9 119.6(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C10 120.7(3) . . ? C5 C4 C10 119.8(3) . . ? C6 C5 C4 120.8(3) . . ? C6 C5 C11 119.9(3) . . ? C4 C5 C11 119.2(3) . . ? C1 C6 C5 118.9(3) . . ? C1 C6 C12 120.7(3) . . ? C5 C6 C12 120.4(3) . . ? C1 C7 P1 112.1(2) . . ? C3 C9 P2 110.35(19) . . ? C5 C11 P3 118.4(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H2W O4W 0.85 1.84 2.48(2) 131.0 . O1W H2W O3W 0.85 1.92 2.747(4) 163.6 . O3W H6W O2 0.85 2.64 3.363(4) 143.3 . O2W H3W O7 0.85 2.14 2.929(3) 153.6 2_765 O2 H2A O8 0.82 1.91 2.687(3) 157.6 2_765 O3W H6W O5 0.85 2.39 3.129(4) 146.4 1_545 O7 H7C O8 0.82 1.78 2.597(3) 178.7 2_765 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.792 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.086