# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Pierre Braunstein' _publ_contact_author_email BRAUNSTEIN@CHIMIE.U-STRASBG.FR _publ_section_title ; Anion Effect in the Diastereoselective Formation of Bischelated Ni(II) Complexes with a Novel, Chiral Phosphine Derived from 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) ; loop_ _publ_author_name 'Pierre Braunstein' "Matthew O'Reilly" 'Roberto Pattacini' # Attachment 'compound2_revised.cif' data_2.3C3H6O _database_code_depnum_ccdc_archive 'CCDC 724930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42H50N4NiP2,0.5(C6H12O2),2(C3H6O),Cl4 Ni' _chemical_formula_sum 'C51 H68 Cl4 N4 Ni2 O3 P2' _chemical_formula_weight 1106.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.3393 1.1124 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' 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' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6254(3) _cell_length_b 13.0726(5) _cell_length_c 19.4149(7) _cell_angle_alpha 82.882(2) _cell_angle_beta 82.801(2) _cell_angle_gamma 86.872(2) _cell_volume 2652.79(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12452 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25907 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 12083 _reflns_number_gt 8595 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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. Four carbons of one of the seven membered cycles were found disordered in two position with equal occupancy factors. The two images were refined anisotropically, except C22A, C22B, C26A and C26B which were refined isotropically. Distances C26B-N4, C26A-N4, C25-C26A and C25-C26B were restrained to match the appropriate geometry. One of the acetone molecules was found disordered in two positions with no atom in common and with equal occupancy factors. ; _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^)+(0.0531P)^2^+1.8799P] 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 12083 _refine_ls_number_parameters 655 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.015 _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 0.79669(3) 0.02415(3) 0.724988(19) 0.02401(11) Uani 1 1 d . A . Ni2 Ni 1.28707(4) -0.12038(4) 0.74049(2) 0.03522(12) Uani 1 1 d . . . P1 P 0.83491(7) 0.05708(6) 0.82510(4) 0.02263(17) Uani 1 1 d . A . P2 P 0.79647(7) 0.17819(6) 0.67191(4) 0.02584(18) Uani 1 1 d . . . N1 N 0.7587(2) -0.1087(2) 0.77957(13) 0.0261(6) Uani 1 1 d . . . N2 N 0.8004(3) -0.2385(2) 0.86916(15) 0.0376(7) Uani 1 1 d . . . N3 N 0.7836(2) -0.0126(2) 0.63253(13) 0.0271(6) Uani 1 1 d . . . N4 N 0.7479(2) 0.0324(2) 0.51503(13) 0.0354(7) Uani 1 1 d D . . Cl1 Cl 1.38471(9) -0.25814(8) 0.69468(5) 0.0520(3) Uani 1 1 d . . . Cl2 Cl 1.25326(10) -0.14325(12) 0.85816(5) 0.0732(4) Uani 1 1 d . . . Cl3 Cl 1.09188(7) -0.09384(7) 0.70339(4) 0.0401(2) Uani 1 1 d . . . Cl4 Cl 1.40180(10) 0.02263(8) 0.70791(7) 0.0624(3) Uani 1 1 d . . . C1 C 0.8960(3) -0.0701(2) 0.86258(15) 0.0256(7) Uani 1 1 d . . . H1 H 0.9847 -0.0801 0.8429 0.031 Uiso 1 1 calc R A . C2 C 0.8896(3) -0.0757(3) 0.94254(15) 0.0290(7) Uani 1 1 d . A . H2A H 0.9215 -0.0121 0.9533 0.035 Uiso 1 1 calc R . . H2B H 0.8010 -0.0779 0.9619 0.035 Uiso 1 1 calc R . . C3 C 0.9607(3) -0.1650(3) 0.98026(18) 0.0397(8) Uani 1 1 d . . . H3A H 0.9601 -0.1532 1.0287 0.048 Uiso 1 1 calc R A . H3B H 1.0485 -0.1668 0.9592 0.048 Uiso 1 1 calc R . . C4 C 0.9046(4) -0.2697(3) 0.9782(2) 0.0476(10) Uani 1 1 d . A . H4A H 0.9539 -0.3232 1.0034 0.057 Uiso 1 1 calc R . . H4B H 0.8183 -0.2697 1.0015 0.057 Uiso 1 1 calc R . . C5 C 0.9043(4) -0.2934(3) 0.9050(2) 0.0485(10) Uani 1 1 d . A . H5A H 0.9850 -0.2750 0.8784 0.058 Uiso 1 1 calc R . . H5B H 0.8966 -0.3671 0.9056 0.058 Uiso 1 1 calc R . . C6 C 0.8153(3) -0.1442(2) 0.83414(16) 0.0277(7) Uani 1 1 d . A . C7 C 0.6656(3) -0.1765(3) 0.75899(17) 0.0335(8) Uani 1 1 d . A . H7A H 0.7093 -0.2250 0.7293 0.040 Uiso 1 1 calc R . . H7B H 0.6049 -0.1352 0.7329 0.040 Uiso 1 1 calc R . . C8 C 0.5968(3) -0.2348(3) 0.82391(18) 0.0388(9) Uani 1 1 d . . . H8A H 0.5545 -0.1867 0.8544 0.047 Uiso 1 1 calc R A . H8B H 0.5334 -0.2773 0.8112 0.047 Uiso 1 1 calc R . . C9 C 0.6941(4) -0.3015(3) 0.8608(2) 0.0481(10) Uani 1 1 d . A . H9A H 0.6556 -0.3312 0.9064 0.058 Uiso 1 1 calc R . . H9B H 0.7248 -0.3574 0.8339 0.058 Uiso 1 1 calc R . . C10 C 0.9528(3) 0.1489(2) 0.83329(15) 0.0253(7) Uani 1 1 d . . . C11 C 1.0818(3) 0.1196(3) 0.82319(16) 0.0298(7) Uani 1 1 d . A . H11 H 1.1065 0.0516 0.8172 0.036 Uiso 1 1 calc R . . C12 C 1.1729(3) 0.1923(3) 0.82208(18) 0.0378(8) Uani 1 1 d . . . H12 H 1.2587 0.1731 0.8150 0.045 Uiso 1 1 calc R A . C13 C 1.1359(3) 0.2929(3) 0.8314(2) 0.0451(10) Uani 1 1 d . A . H13 H 1.1972 0.3411 0.8314 0.054 Uiso 1 1 calc R . . C14 C 1.0090(3) 0.3229(3) 0.8409(2) 0.0427(9) Uani 1 1 d . . . H14 H 0.9848 0.3910 0.8467 0.051 Uiso 1 1 calc R A . C15 C 0.9179(3) 0.2507(3) 0.84174(16) 0.0309(7) Uani 1 1 d . A . H15 H 0.8324 0.2708 0.8480 0.037 Uiso 1 1 calc R . . C16 C 0.6927(3) 0.0872(2) 0.88301(15) 0.0245(6) Uani 1 1 d . . . C17 C 0.6968(3) 0.1347(3) 0.94304(16) 0.0293(7) Uani 1 1 d . A . H17 H 0.7746 0.1520 0.9547 0.035 Uiso 1 1 calc R . . C18 C 0.5866(3) 0.1565(3) 0.98538(18) 0.0378(8) Uani 1 1 d . . . H18 H 0.5899 0.1883 1.0253 0.045 Uiso 1 1 calc R A . C19 C 0.4713(3) 0.1304(3) 0.96794(19) 0.0417(9) Uani 1 1 d . A . H19 H 0.3969 0.1467 0.9957 0.050 Uiso 1 1 calc R . . C20 C 0.4650(3) 0.0808(3) 0.91004(19) 0.0382(8) Uani 1 1 d . . . H20 H 0.3871 0.0614 0.8998 0.046 Uiso 1 1 calc R A . C21 C 0.5754(3) 0.0597(3) 0.86701(17) 0.0312(7) Uani 1 1 d . A . H21 H 0.5713 0.0271 0.8274 0.037 Uiso 1 1 calc R . . C22A C 0.6913(7) 0.1496(5) 0.6053(4) 0.0217(16) Uiso 0.50 1 d P A 1 H22A H 0.6060 0.1363 0.6293 0.026 Uiso 0.50 1 calc PR A 1 C22B C 0.7217(7) 0.1715(6) 0.5923(4) 0.0278(18) Uiso 0.50 1 d P A 2 H22B H 0.7667 0.2148 0.5531 0.033 Uiso 0.50 1 calc PR A 2 C23A C 0.6821(6) 0.2397(5) 0.5486(3) 0.0248(13) Uani 0.50 1 d P A 1 H23A H 0.6794 0.3039 0.5692 0.030 Uiso 0.50 1 calc PR A 1 H23B H 0.7570 0.2386 0.5145 0.030 Uiso 0.50 1 calc PR A 1 C23B C 0.5794(6) 0.2012(6) 0.5982(4) 0.0362(16) Uani 0.50 1 d P A 2 H23C H 0.5630 0.2592 0.6253 0.043 Uiso 0.50 1 calc PR A 2 H23D H 0.5322 0.1438 0.6232 0.043 Uiso 0.50 1 calc PR A 2 C24A C 0.5663(14) 0.235(2) 0.5127(12) 0.035(4) Uani 0.50 1 d P A 1 H24A H 0.4922 0.2495 0.5452 0.042 Uiso 0.50 1 calc PR A 1 H24B H 0.5690 0.2899 0.4738 0.042 Uiso 0.50 1 calc PR A 1 C24B C 0.5310(16) 0.231(2) 0.5249(11) 0.036(4) Uani 0.50 1 d P A 2 H24C H 0.4417 0.2523 0.5307 0.044 Uiso 0.50 1 calc PR A 2 H24D H 0.5783 0.2877 0.4989 0.044 Uiso 0.50 1 calc PR A 2 C25 C 0.5506(3) 0.1359(3) 0.48596(19) 0.0395(8) Uani 1 1 d D . . H25A H 0.4982 0.1489 0.4481 0.047 Uiso 1 1 calc R A 1 H25B H 0.5048 0.0908 0.5230 0.047 Uiso 1 1 calc R A 1 C27 C 0.7476(3) 0.0531(3) 0.58138(16) 0.0320(8) Uani 1 1 d . A . C28 C 0.8102(3) -0.0614(3) 0.49087(17) 0.0379(8) Uani 1 1 d . A . H28A H 0.8598 -0.0442 0.4459 0.046 Uiso 1 1 calc R . . H28B H 0.7464 -0.1088 0.4849 0.046 Uiso 1 1 calc R . . C29 C 0.8958(3) -0.1127(3) 0.54242(18) 0.0384(8) Uani 1 1 d . . . H29A H 0.9715 -0.0736 0.5401 0.046 Uiso 1 1 calc R A . H29B H 0.9214 -0.1818 0.5315 0.046 Uiso 1 1 calc R . . C30 C 0.8226(3) -0.1175(3) 0.61552(17) 0.0333(8) Uani 1 1 d . A . H30A H 0.7481 -0.1580 0.6177 0.040 Uiso 1 1 calc R . . H30B H 0.8757 -0.1509 0.6495 0.040 Uiso 1 1 calc R . . C31 C 0.7095(3) 0.2797(3) 0.71675(16) 0.0301(7) Uani 1 1 d . A . C32 C 0.7615(3) 0.3726(3) 0.72308(18) 0.0380(8) Uani 1 1 d . . . H32 H 0.8422 0.3872 0.7007 0.046 Uiso 1 1 calc R A . C33 C 0.6951(4) 0.4437(3) 0.7623(2) 0.0513(10) Uani 1 1 d . A . H33 H 0.7309 0.5059 0.7658 0.062 Uiso 1 1 calc R . . C34 C 0.5768(4) 0.4226(4) 0.7958(3) 0.0666(13) Uani 1 1 d . . . H34 H 0.5323 0.4702 0.8225 0.080 Uiso 1 1 calc R A . C35 C 0.5238(4) 0.3305(4) 0.7900(2) 0.0647(13) Uani 1 1 d . A . H35 H 0.4437 0.3160 0.8133 0.078 Uiso 1 1 calc R . . C36 C 0.5884(3) 0.2597(3) 0.75017(19) 0.0445(9) Uani 1 1 d . . . H36 H 0.5509 0.1986 0.7457 0.053 Uiso 1 1 calc R A . C37 C 0.9473(3) 0.2324(2) 0.63354(16) 0.0286(7) Uani 1 1 d . A . C38 C 1.0580(3) 0.1849(3) 0.65400(16) 0.0333(8) Uani 1 1 d . . . H38 H 1.0548 0.1228 0.6831 0.040 Uiso 1 1 calc R A . C39 C 1.1742(3) 0.2291(3) 0.63146(18) 0.0396(8) Uani 1 1 d . A . H39 H 1.2484 0.1968 0.6456 0.047 Uiso 1 1 calc R . . C40 C 1.1793(3) 0.3210(3) 0.58799(19) 0.0401(9) Uani 1 1 d . . . H40 H 1.2568 0.3515 0.5737 0.048 Uiso 1 1 calc R A . C41 C 1.0691(3) 0.3680(3) 0.56554(19) 0.0384(8) Uani 1 1 d . A . H41 H 1.0734 0.4286 0.5349 0.046 Uiso 1 1 calc R . . C42 C 0.9527(3) 0.3252(3) 0.58839(17) 0.0328(7) Uani 1 1 d . . . H42 H 0.8787 0.3576 0.5740 0.039 Uiso 1 1 calc R A . C43 C 0.0288(5) 0.6119(4) 0.6946(3) 0.0699(14) Uani 1 1 d . . . C44 C 0.1143(7) 0.5766(6) 0.7473(4) 0.141(3) Uani 1 1 d . . . H44A H 0.0652 0.5508 0.7903 0.211 Uiso 1 1 calc R . . H44B H 0.1625 0.6332 0.7551 0.211 Uiso 1 1 calc R . . H44C H 0.1711 0.5227 0.7310 0.211 Uiso 1 1 calc R . . C45 C 0.0866(6) 0.6456(4) 0.6238(3) 0.0831(16) Uani 1 1 d . . . H45A H 0.0221 0.6554 0.5928 0.125 Uiso 1 1 calc R . . H45B H 0.1483 0.5941 0.6086 0.125 Uiso 1 1 calc R . . H45C H 0.1275 0.7094 0.6233 0.125 Uiso 1 1 calc R . . C46 C 0.6283(4) 0.5319(3) 0.5785(2) 0.0477(10) Uani 1 1 d . . . C47 C 0.4976(4) 0.5004(3) 0.6083(2) 0.0568(11) Uani 1 1 d . . . H47A H 0.4718 0.4480 0.5830 0.085 Uiso 1 1 calc R . . H47B H 0.4396 0.5592 0.6043 0.085 Uiso 1 1 calc R . . H47C H 0.4974 0.4738 0.6566 0.085 Uiso 1 1 calc R . . C48 C 0.6763(4) 0.6257(3) 0.6016(2) 0.0530(10) Uani 1 1 d . . . H48A H 0.7629 0.6345 0.5818 0.079 Uiso 1 1 calc R . . H48B H 0.6713 0.6178 0.6517 0.079 Uiso 1 1 calc R . . H48C H 0.6254 0.6851 0.5863 0.079 Uiso 1 1 calc R . . C49A C 0.2111(10) 0.5474(6) 0.9586(7) 0.065(3) Uani 0.50 1 d P B 2 C49B C 0.3308(13) 0.5491(11) 0.9625(7) 0.090(4) Uani 0.50 1 d P C 1 C50A C 0.261(5) 0.581(3) 1.027(2) 0.083(10) Uani 0.50 1 d P B 2 H50A H 0.2061 0.5555 1.0676 0.124 Uiso 0.50 1 calc PR B 2 H50B H 0.2612 0.6550 1.0232 0.124 Uiso 0.50 1 calc PR B 2 H50C H 0.3456 0.5529 1.0303 0.124 Uiso 0.50 1 calc PR B 2 C50B C 0.292(2) 0.563(2) 0.8911(15) 0.094(6) Uani 0.50 1 d P C 1 H50D H 0.3157 0.6298 0.8681 0.160 Uiso 0.50 1 calc PR C 1 H50E H 0.2014 0.5583 0.8941 0.160 Uiso 0.50 1 calc PR C 1 H50F H 0.3329 0.5106 0.8649 0.160 Uiso 0.50 1 calc PR C 1 C51A C 0.294(4) 0.546(4) 0.9089(19) 0.22(2) Uani 0.50 1 d P B 2 H51A H 0.2586 0.5236 0.8702 0.375 Uiso 0.50 1 calc PR B 2 H51B H 0.3616 0.4985 0.9217 0.375 Uiso 0.50 1 calc PR B 2 H51C H 0.3256 0.6135 0.8958 0.375 Uiso 0.50 1 calc PR B 2 C51B C 0.240(6) 0.594(4) 1.019(3) 0.104(13) Uani 0.50 1 d P C 1 H51D H 0.2829 0.5996 1.0586 0.177 Uiso 0.50 1 calc PR C 1 H51E H 0.1694 0.5496 1.0325 0.177 Uiso 0.50 1 calc PR C 1 H51F H 0.2085 0.6611 1.0008 0.177 Uiso 0.50 1 calc PR C 1 O1 O -0.0828(4) 0.6155(4) 0.7114(3) 0.136(2) Uani 1 1 d . . . O2 O 0.6934(3) 0.4837(3) 0.53694(18) 0.0728(9) Uani 1 1 d . . . O3A O 0.1117(7) 0.5115(6) 0.9547(5) 0.095(3) Uani 0.50 1 d P B 2 O3B O 0.4394(10) 0.5165(12) 0.9609(6) 0.172(6) Uani 0.50 1 d P C 1 C26B C 0.6906(5) 0.1080(6) 0.4634(3) 0.038(2) Uiso 0.50 1 d PD A 2 H26A H 0.6974 0.0798 0.4191 0.045 Uiso 0.50 1 calc PR A 2 H26B H 0.7384 0.1704 0.4562 0.045 Uiso 0.50 1 calc PR A 2 C26A C 0.6714(5) 0.0798(6) 0.4600(2) 0.035(2) Uiso 0.50 1 d PD A 1 H26C H 0.6499 0.0260 0.4337 0.042 Uiso 0.50 1 calc PR A 1 H26D H 0.7232 0.1279 0.4280 0.042 Uiso 0.50 1 calc PR A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0272(2) 0.0264(2) 0.0204(2) -0.00688(16) -0.00531(15) -0.00437(16) Ni2 0.0320(2) 0.0435(3) 0.0326(2) -0.0119(2) -0.00619(17) -0.00086(19) P1 0.0233(4) 0.0260(4) 0.0200(4) -0.0052(3) -0.0040(3) -0.0049(3) P2 0.0299(4) 0.0285(4) 0.0202(4) -0.0057(3) -0.0051(3) 0.0011(3) N1 0.0275(13) 0.0285(15) 0.0241(13) -0.0071(11) -0.0034(10) -0.0079(11) N2 0.0444(17) 0.0278(16) 0.0441(18) 0.0004(13) -0.0211(13) -0.0074(13) N3 0.0270(13) 0.0323(15) 0.0244(14) -0.0101(11) -0.0041(10) -0.0043(11) N4 0.0342(15) 0.0504(19) 0.0241(14) -0.0138(13) -0.0079(11) 0.0067(13) Cl1 0.0513(6) 0.0547(6) 0.0568(6) -0.0276(5) -0.0172(4) 0.0095(5) Cl2 0.0554(6) 0.1290(12) 0.0332(6) -0.0112(6) -0.0078(4) 0.0250(7) Cl3 0.0302(4) 0.0545(6) 0.0382(5) -0.0132(4) -0.0058(3) -0.0044(4) Cl4 0.0518(6) 0.0472(6) 0.0929(9) -0.0056(6) -0.0267(6) -0.0082(5) C1 0.0246(15) 0.0276(17) 0.0261(16) -0.0043(13) -0.0065(12) -0.0037(13) C2 0.0358(17) 0.0288(18) 0.0235(16) -0.0039(13) -0.0059(13) -0.0027(14) C3 0.049(2) 0.042(2) 0.0311(19) -0.0018(16) -0.0167(16) -0.0021(17) C4 0.059(2) 0.036(2) 0.049(2) 0.0031(18) -0.0218(19) -0.0003(18) C5 0.063(3) 0.029(2) 0.058(3) -0.0032(18) -0.026(2) 0.0055(18) C6 0.0270(16) 0.0290(18) 0.0288(17) -0.0069(14) -0.0051(13) -0.0044(13) C7 0.0326(17) 0.038(2) 0.0332(18) -0.0081(15) -0.0090(14) -0.0147(15) C8 0.0378(19) 0.046(2) 0.0347(19) -0.0039(16) -0.0069(15) -0.0191(17) C9 0.062(2) 0.036(2) 0.050(2) 0.0031(18) -0.0183(19) -0.0231(19) C10 0.0286(16) 0.0315(18) 0.0172(15) -0.0035(12) -0.0046(11) -0.0069(13) C11 0.0311(17) 0.0320(18) 0.0270(17) -0.0045(14) -0.0042(13) -0.0054(14) C12 0.0285(17) 0.045(2) 0.041(2) -0.0031(17) -0.0066(14) -0.0098(16) C13 0.042(2) 0.038(2) 0.058(2) -0.0002(18) -0.0115(17) -0.0196(17) C14 0.045(2) 0.0291(19) 0.056(2) -0.0075(17) -0.0078(17) -0.0104(16) C15 0.0318(17) 0.0316(19) 0.0303(18) -0.0034(14) -0.0047(13) -0.0068(14) C16 0.0250(15) 0.0236(16) 0.0246(16) -0.0009(12) -0.0035(12) -0.0028(12) C17 0.0292(16) 0.0343(19) 0.0247(17) -0.0049(14) -0.0024(12) -0.0030(14) C18 0.040(2) 0.043(2) 0.0285(18) -0.0070(16) 0.0052(14) -0.0020(16) C19 0.0296(18) 0.047(2) 0.043(2) -0.0026(18) 0.0110(15) 0.0014(16) C20 0.0249(17) 0.042(2) 0.046(2) 0.0046(17) -0.0044(14) -0.0064(15) C21 0.0305(17) 0.0330(19) 0.0303(18) 0.0009(14) -0.0071(13) -0.0063(14) C23A 0.031(3) 0.023(3) 0.022(3) -0.001(2) -0.009(2) -0.001(3) C23B 0.036(4) 0.036(4) 0.038(4) -0.007(3) -0.005(3) -0.002(3) C24A 0.022(8) 0.035(6) 0.049(8) -0.002(5) -0.013(6) 0.009(7) C24B 0.025(8) 0.048(6) 0.040(7) -0.011(6) -0.014(6) 0.003(7) C25 0.0353(18) 0.049(2) 0.039(2) -0.0107(17) -0.0177(15) -0.0026(16) C27 0.0280(16) 0.046(2) 0.0253(17) -0.0129(15) -0.0077(13) 0.0024(15) C28 0.0402(19) 0.048(2) 0.0277(18) -0.0146(16) 0.0000(14) -0.0094(17) C29 0.043(2) 0.036(2) 0.036(2) -0.0147(16) 0.0045(15) -0.0022(16) C30 0.0377(18) 0.0343(19) 0.0300(18) -0.0113(15) -0.0023(14) -0.0083(15) C31 0.0392(18) 0.0283(18) 0.0222(16) -0.0034(13) -0.0033(13) 0.0032(14) C32 0.0411(19) 0.041(2) 0.0345(19) -0.0149(16) -0.0044(15) 0.0029(16) C33 0.066(3) 0.043(2) 0.047(2) -0.0180(19) -0.0010(19) 0.000(2) C34 0.072(3) 0.050(3) 0.074(3) -0.028(2) 0.020(2) 0.011(2) C35 0.057(3) 0.052(3) 0.076(3) -0.018(2) 0.033(2) 0.001(2) C36 0.047(2) 0.035(2) 0.046(2) -0.0037(17) 0.0135(17) 0.0017(17) C37 0.0343(17) 0.0280(17) 0.0238(16) -0.0059(13) -0.0020(13) 0.0000(14) C38 0.0378(18) 0.037(2) 0.0234(17) -0.0024(14) -0.0020(13) 0.0066(15) C39 0.0302(18) 0.051(2) 0.036(2) -0.0062(17) -0.0041(14) 0.0090(16) C40 0.0317(18) 0.047(2) 0.042(2) -0.0074(17) 0.0001(15) -0.0074(16) C41 0.042(2) 0.033(2) 0.040(2) -0.0025(16) -0.0035(15) -0.0070(16) C42 0.0339(18) 0.0306(18) 0.0346(19) -0.0026(15) -0.0076(14) -0.0005(14) C43 0.054(3) 0.060(3) 0.098(4) -0.003(3) -0.020(3) -0.019(2) C44 0.129(6) 0.156(7) 0.127(6) 0.083(5) -0.051(5) -0.066(5) C45 0.101(4) 0.074(4) 0.079(4) -0.010(3) -0.023(3) -0.017(3) C46 0.050(2) 0.042(2) 0.052(2) -0.0036(19) -0.0162(19) 0.0051(19) C47 0.050(2) 0.049(3) 0.073(3) -0.008(2) -0.009(2) -0.009(2) C48 0.050(2) 0.051(3) 0.060(3) -0.005(2) -0.0148(19) -0.008(2) C49A 0.056(6) 0.026(4) 0.113(10) -0.013(5) -0.012(6) 0.007(4) C49B 0.089(9) 0.107(10) 0.074(9) -0.028(7) -0.010(6) 0.035(7) C50A 0.13(2) 0.053(9) 0.064(13) -0.019(9) 0.013(16) 0.001(13) C50B 0.097(12) 0.114(14) 0.065(14) -0.005(10) 0.007(8) 0.003(10) C51A 0.28(4) 0.32(6) 0.07(2) -0.09(3) 0.00(2) 0.05(3) C51B 0.110(18) 0.12(3) 0.082(18) -0.039(17) -0.014(13) 0.014(17) O1 0.065(3) 0.167(5) 0.178(5) -0.016(4) -0.007(3) -0.041(3) O2 0.072(2) 0.071(2) 0.077(2) -0.0291(19) 0.0028(17) 0.0019(18) O3A 0.079(5) 0.055(4) 0.150(8) 0.006(5) -0.023(5) -0.012(4) O3B 0.112(8) 0.269(16) 0.151(10) -0.103(10) -0.044(7) 0.103(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 1.938(2) . ? Ni1 N1 1.953(3) . ? Ni1 P1 2.1337(8) . ? Ni1 P2 2.1454(9) . ? Ni2 Cl1 2.2522(11) . ? Ni2 Cl2 2.2525(11) . ? Ni2 Cl4 2.2680(11) . ? Ni2 Cl3 2.2747(9) . ? P1 C10 1.816(3) . ? P1 C16 1.822(3) . ? P1 C1 1.848(3) . ? P2 C37 1.822(3) . ? P2 C31 1.823(3) . ? P2 C22B 1.838(7) . ? P2 C22A 1.894(7) . ? N1 C6 1.307(4) . ? N1 C7 1.486(4) . ? N2 C6 1.338(4) . ? N2 C9 1.470(4) . ? N2 C5 1.484(5) . ? N3 C27 1.311(4) . ? N3 C30 1.475(4) . ? N4 C27 1.348(4) . ? N4 C28 1.462(4) . ? N4 C26A 1.4787(10) . ? N4 C26B 1.4814(10) . ? C1 C6 1.524(4) . ? C1 C2 1.538(4) . ? C1 H1 0.9800 . ? C2 C3 1.517(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.530(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.491(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.515(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.509(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.385(5) . ? C10 C11 1.400(4) . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.380(5) . ? C12 H12 0.9300 . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.385(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.393(4) . ? C16 C21 1.398(4) . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 C19 1.381(5) . ? C18 H18 0.9300 . ? C19 C20 1.377(5) . ? C19 H19 0.9300 . ? C20 C21 1.388(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22A C27 1.469(7) . ? C22A C23A 1.518(9) . ? C22A H22A 0.9800 . ? C22B C23B 1.534(10) . ? C22B C27 1.593(8) . ? C22B H22B 0.9800 . ? C23A C24A 1.49(2) . ? C23A H23A 0.9700 . ? C23A H23B 0.9700 . ? C23B C24B 1.57(2) . ? C23B H23C 0.9700 . ? C23B H23D 0.9700 . ? C24A C25 1.48(3) . ? C24A H24A 0.9700 . ? C24A H24B 0.9700 . ? C24B C25 1.52(3) . ? C24B H24C 0.9700 . ? C24B H24D 0.9700 . ? C25 C26A 1.506(4) . ? C25 C26B 1.535(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C28 C29 1.508(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.526(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.387(5) . ? C31 C36 1.390(5) . ? C32 C33 1.382(5) . ? C32 H32 0.9300 . ? C33 C34 1.366(6) . ? C33 H33 0.9300 . ? C34 C35 1.379(6) . ? C34 H34 0.9300 . ? C35 C36 1.379(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.379(5) . ? C37 C42 1.405(5) . ? C38 C39 1.389(5) . ? C38 H38 0.9300 . ? C39 C40 1.379(5) . ? C39 H39 0.9300 . ? C40 C41 1.386(5) . ? C40 H40 0.9300 . ? C41 C42 1.384(5) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 O1 1.190(6) . ? C43 C45 1.460(7) . ? C43 C44 1.468(8) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 O2 1.210(5) . ? C46 C48 1.492(6) . ? C46 C47 1.495(6) . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49A O3A 1.194(11) . ? C49A C51A 1.22(4) . ? C49A C50A 1.60(5) . ? C49B O3B 1.206(14) . ? C49B C50B 1.48(3) . ? C49B C51B 1.52(5) . ? C50A H50A 0.9600 . ? C50A H50B 0.9600 . ? C50A H50C 0.9600 . ? C50B H50D 0.9600 . ? C50B H50E 0.9600 . ? C50B H50F 0.9600 . ? C51A H51A 0.9600 . ? C51A H51B 0.9600 . ? C51A H51C 0.9600 . ? C51B H51D 0.9600 . ? C51B H51E 0.9600 . ? C51B H51F 0.9600 . ? C26B H26A 0.9700 . ? C26B H26B 0.9700 . ? C26A H26C 0.9700 . ? C26A H26D 0.9700 . ? 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 N3 Ni1 N1 99.00(11) . . ? N3 Ni1 P1 172.85(8) . . ? N1 Ni1 P1 80.41(7) . . ? N3 Ni1 P2 83.11(8) . . ? N1 Ni1 P2 167.69(8) . . ? P1 Ni1 P2 98.99(3) . . ? Cl1 Ni2 Cl2 113.07(5) . . ? Cl1 Ni2 Cl4 111.07(5) . . ? Cl2 Ni2 Cl4 107.88(5) . . ? Cl1 Ni2 Cl3 108.81(4) . . ? Cl2 Ni2 Cl3 106.01(4) . . ? Cl4 Ni2 Cl3 109.85(4) . . ? C10 P1 C16 107.41(14) . . ? C10 P1 C1 106.20(14) . . ? C16 P1 C1 105.67(14) . . ? C10 P1 Ni1 121.10(10) . . ? C16 P1 Ni1 113.64(10) . . ? C1 P1 Ni1 101.33(10) . . ? C37 P2 C31 105.60(15) . . ? C37 P2 C22B 100.1(3) . . ? C31 P2 C22B 106.5(2) . . ? C37 P2 C22A 114.0(3) . . ? C31 P2 C22A 104.7(2) . . ? C37 P2 Ni1 118.82(11) . . ? C31 P2 Ni1 118.10(11) . . ? C22B P2 Ni1 105.6(3) . . ? C22A P2 Ni1 94.6(2) . . ? C6 N1 C7 116.5(3) . . ? C6 N1 Ni1 122.6(2) . . ? C7 N1 Ni1 120.9(2) . . ? C6 N2 C9 121.6(3) . . ? C6 N2 C5 121.2(3) . . ? C9 N2 C5 115.8(3) . . ? C27 N3 C30 116.5(3) . . ? C27 N3 Ni1 123.4(2) . . ? C30 N3 Ni1 120.0(2) . . ? C27 N4 C28 121.6(3) . . ? C27 N4 C26A 130.2(3) . . ? C28 N4 C26A 107.0(3) . . ? C27 N4 C26B 120.2(4) . . ? C28 N4 C26B 118.1(4) . . ? C6 C1 C2 117.0(2) . . ? C6 C1 P1 102.3(2) . . ? C2 C1 P1 110.7(2) . . ? C6 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? P1 C1 H1 108.8 . . ? C3 C2 C1 117.7(3) . . ? C3 C2 H2A 107.9 . . ? C1 C2 H2A 107.9 . . ? C3 C2 H2B 107.9 . . ? C1 C2 H2B 107.9 . . ? H2A C2 H2B 107.2 . . ? C2 C3 C4 113.4(3) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 111.6(3) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N2 C5 C4 113.6(3) . . ? N2 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? N2 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N1 C6 N2 124.5(3) . . ? N1 C6 C1 117.2(3) . . ? N2 C6 C1 118.1(3) . . ? N1 C7 C8 109.5(3) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C7 107.8(3) . . ? C9 C8 H8A 110.1 . . ? C7 C8 H8A 110.1 . . ? C9 C8 H8B 110.1 . . ? C7 C8 H8B 110.1 . . ? H8A C8 H8B 108.5 . . ? N2 C9 C8 109.4(3) . . ? N2 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N2 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C15 C10 C11 119.2(3) . . ? C15 C10 P1 121.0(2) . . ? C11 C10 P1 119.4(2) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C10 120.8(3) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C17 C16 C21 119.0(3) . . ? C17 C16 P1 122.6(2) . . ? C21 C16 P1 118.4(2) . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 119.5(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C20 C19 C18 121.0(3) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C16 120.2(3) . . ? C20 C21 H21 119.9 . . ? C16 C21 H21 119.9 . . ? C27 C22A C23A 115.6(5) . . ? C27 C22A P2 103.7(4) . . ? C23A C22A P2 111.5(5) . . ? C27 C22A H22A 108.6 . . ? C23A C22A H22A 108.6 . . ? P2 C22A H22A 108.6 . . ? C23B C22B C27 111.6(6) . . ? C23B C22B P2 114.9(5) . . ? C27 C22B P2 101.4(4) . . ? C23B C22B H22B 109.6 . . ? C27 C22B H22B 109.6 . . ? P2 C22B H22B 109.6 . . ? C24A C23A C22A 111.4(10) . . ? C24A C23A H23A 109.4 . . ? C22A C23A H23A 109.4 . . ? C24A C23A H23B 109.4 . . ? C22A C23A H23B 109.4 . . ? H23A C23A H23B 108.0 . . ? C22B C23B C24B 112.5(8) . . ? C22B C23B H23C 109.1 . . ? C24B C23B H23C 109.1 . . ? C22B C23B H23D 109.1 . . ? C24B C23B H23D 109.1 . . ? H23C C23B H23D 107.8 . . ? C25 C24A C23A 115.1(15) . . ? C25 C24A H24A 108.5 . . ? C23A C24A H24A 108.5 . . ? C25 C24A H24B 108.5 . . ? C23A C24A H24B 108.5 . . ? H24A C24A H24B 107.5 . . ? C25 C24B C23B 107.5(17) . . ? C25 C24B H24C 110.2 . . ? C23B C24B H24C 110.2 . . ? C25 C24B H24D 110.2 . . ? C23B C24B H24D 110.2 . . ? H24C C24B H24D 108.5 . . ? C24A C25 C26A 115.8(7) . . ? C26A C25 C24B 130.1(8) . . ? C24A C25 C26B 99.0(7) . . ? C24B C25 C26B 113.7(8) . . ? C24A C25 H25A 108.3 . . ? C26A C25 H25A 108.3 . . ? C24B C25 H25A 105.7 . . ? C26B C25 H25A 114.8 . . ? C24A C25 H25B 108.3 . . ? C26A C25 H25B 108.3 . . ? C24B C25 H25B 94.8 . . ? C26B C25 H25B 118.2 . . ? H25A C25 H25B 107.4 . . ? N3 C27 N4 124.8(3) . . ? N3 C27 C22A 112.7(4) . . ? N4 C27 C22A 122.1(4) . . ? N3 C27 C22B 119.7(4) . . ? N4 C27 C22B 114.7(4) . . ? N4 C28 C29 110.9(3) . . ? N4 C28 H28A 109.5 . . ? C29 C28 H28A 109.5 . . ? N4 C28 H28B 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 108.0 . . ? C28 C29 C30 108.2(3) . . ? C28 C29 H29A 110.1 . . ? C30 C29 H29A 110.1 . . ? C28 C29 H29B 110.1 . . ? C30 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? N3 C30 C29 110.3(3) . . ? N3 C30 H30A 109.6 . . ? C29 C30 H30A 109.6 . . ? N3 C30 H30B 109.6 . . ? C29 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C36 118.6(3) . . ? C32 C31 P2 123.2(3) . . ? C36 C31 P2 118.0(3) . . ? C33 C32 C31 120.9(3) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C34 C33 C32 120.0(4) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.8(4) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 120.7(4) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C35 C36 C31 119.9(4) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C38 C37 C42 119.6(3) . . ? C38 C37 P2 118.6(2) . . ? C42 C37 P2 121.6(2) . . ? C37 C38 C39 120.5(3) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C40 C39 C38 119.9(3) . . ? C40 C39 H39 120.1 . . ? C38 C39 H39 120.1 . . ? C39 C40 C41 120.1(3) . . ? C39 C40 H40 120.0 . . ? C41 C40 H40 120.0 . . ? C42 C41 C40 120.5(3) . . ? C42 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C41 C42 C37 119.4(3) . . ? C41 C42 H42 120.3 . . ? C37 C42 H42 120.3 . . ? O1 C43 C45 122.9(5) . . ? O1 C43 C44 119.6(6) . . ? C45 C43 C44 117.5(5) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O2 C46 C48 120.8(4) . . ? O2 C46 C47 121.6(4) . . ? C48 C46 C47 117.6(4) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? O3A C49A C51A 118(3) . . ? O3A C49A C50A 128(2) . . ? C51A C49A C50A 113(3) . . ? O3B C49B C50B 110.3(15) . . ? O3B C49B C51B 133(3) . . ? C50B C49B C51B 116(3) . . ? C49A C50A H50A 109.5 . . ? C49A C50A H50B 109.5 . . ? H50A C50A H50B 109.5 . . ? C49A C50A H50C 109.5 . . ? H50A C50A H50C 109.5 . . ? H50B C50A H50C 109.5 . . ? C49A C51A H51A 109.5 . . ? C49A C51A H51B 109.5 . . ? H51A C51A H51B 109.5 . . ? C49A C51A H51C 109.5 . . ? H51A C51A H51C 109.5 . . ? H51B C51A H51C 109.5 . . ? N4 C26B C25 113.2(3) . . ? N4 C26B H26A 108.9 . . ? C25 C26B H26A 108.9 . . ? N4 C26B H26B 108.9 . . ? C25 C26B H26B 108.9 . . ? H26A C26B H26B 107.7 . . ? N4 C26A C25 115.1(3) . . ? N4 C26A H26C 108.5 . . ? C25 C26A H26C 108.5 . . ? N4 C26A H26D 108.5 . . ? C25 C26A H26D 108.5 . . ? H26C C26A H26D 107.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.680 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.153 # Attachment 'compound3_revised.cif' data_3.4CHCl3.Et2O _database_code_depnum_ccdc_archive 'CCDC 724931' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42H50N4 Ni P2, C4 H10 O, 4(C H Cl3), 2(Cl)' _chemical_formula_sum 'C50 H64 Cl14 N4 Ni O P2' _chemical_formula_weight 1354.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.3393 1.1124 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' 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' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.4443(5) _cell_length_b 15.8472(6) _cell_length_c 15.9016(4) _cell_angle_alpha 116.871(2) _cell_angle_beta 95.778(2) _cell_angle_gamma 97.478(2) _cell_volume 3166.49(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 28402 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.986 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30223 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 26.50 _reflns_number_total 13080 _reflns_number_gt 7849 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One of the chloroform molecules was found disordered over three positions with unequal occupancy factors. The six chlorine positions were located, while the carbon atom was refined as occupying one position, although probably disordered. This resulted in C-Cl distances and Cl-C-Cl angles deviating from the ideal ones. The chlorine atoms of the solvent were refined anisotropically with thermal parameters restrained to isotropic ones. The ether molecule was as well found disordered and was isotropically refined with restrained geometrical parameters. ; _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^)+(0.1052P)^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 13080 _refine_ls_number_parameters 678 _refine_ls_number_restraints 58 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.007 _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 0.26265(3) 0.36683(4) 0.68084(3) 0.02636(15) Uani 1 1 d . . . P1 P 0.15069(7) 0.24244(7) 0.61194(7) 0.0275(2) Uani 1 1 d . . . P2 P 0.19107(6) 0.47459(7) 0.76834(6) 0.0268(2) Uani 1 1 d . . . N1 N 0.3305(2) 0.2779(2) 0.5934(2) 0.0260(7) Uani 1 1 d . . . N2 N 0.3500(2) 0.1200(2) 0.4973(2) 0.0349(8) Uani 1 1 d . . . N3 N 0.3727(2) 0.4626(2) 0.7631(2) 0.0277(7) Uani 1 1 d . . . N4 N 0.4453(2) 0.6200(2) 0.8779(2) 0.0354(8) Uani 1 1 d . . . Cl1 Cl 0.35548(7) 0.23040(8) 0.83179(7) 0.0422(3) Uani 1 1 d . . . Cl2 Cl 0.28325(7) 0.50138(8) 0.54801(7) 0.0374(3) Uani 1 1 d . . . Cl3A Cl 0.4036(5) 0.0265(5) 0.9333(5) 0.085(2) Uani 0.40 1 d PU A 1 Cl4A Cl 0.2696(4) 0.1474(5) 1.0126(5) 0.093(2) Uani 0.40 1 d PU A 1 Cl5A Cl 0.2061(9) -0.0207(11) 0.8330(10) 0.082(4) Uani 0.40 1 d PU A 1 Cl4B Cl 0.2172(7) 0.1432(7) 0.9897(7) 0.121(3) Uani 0.40 1 d PU B 2 Cl3B Cl 0.3736(5) 0.0474(5) 0.9816(6) 0.098(3) Uani 0.40 1 d PU C 2 Cl5B Cl 0.2286(9) -0.0316(9) 0.8193(8) 0.053(2) Uani 0.40 1 d PU D 2 Cl22 Cl 0.3330(7) 0.0777(9) 1.0143(7) 0.072(3) Uani 0.20 1 d PU E 3 Cl20 Cl 0.1545(7) 0.0910(8) 0.9237(8) 0.095(3) Uani 0.20 1 d PU F 3 Cl21 Cl 0.2707(10) -0.0367(12) 0.8125(12) 0.082(4) Uani 0.20 1 d PU G 3 Cl6 Cl 0.37468(10) 0.81182(14) 0.66009(10) 0.0792(5) Uani 1 1 d . . . Cl7 Cl 0.17323(9) 0.74094(11) 0.58878(10) 0.0653(4) Uani 1 1 d . . . Cl8 Cl 0.30307(11) 0.72689(11) 0.45892(9) 0.0706(4) Uani 1 1 d . . . Cl9 Cl 0.32194(10) 0.48186(14) 0.28728(13) 0.0883(5) Uani 1 1 d . . . Cl10 Cl 0.48153(8) 0.42683(9) 0.36125(8) 0.0505(3) Uani 1 1 d . . . Cl11 Cl 0.31291(12) 0.28563(12) 0.24539(10) 0.0903(5) Uani 1 1 d . . . Cl12 Cl 0.58008(16) 0.09584(13) 0.78182(12) 0.1026(6) Uani 1 1 d . . . Cl13 Cl 0.57307(10) 0.19994(11) 0.67451(8) 0.0645(4) Uani 1 1 d . . . Cl14 Cl 0.66673(11) 0.29687(14) 0.87079(11) 0.0933(6) Uani 1 1 d . . . C1 C 0.2267(3) 0.1541(3) 0.6028(3) 0.0304(9) Uani 1 1 d . . . H1 H 0.2522 0.1685 0.6684 0.036 Uiso 1 1 calc R . . C2 C 0.1774(3) 0.0482(3) 0.5499(3) 0.0393(10) Uani 1 1 d . . . H2A H 0.1150 0.0418 0.5666 0.047 Uiso 1 1 calc R . . H2B H 0.1691 0.0258 0.4814 0.047 Uiso 1 1 calc R . . C3 C 0.2344(3) -0.0144(3) 0.5751(3) 0.0433(11) Uani 1 1 d . . . H3A H 0.2081 -0.0819 0.5313 0.052 Uiso 1 1 calc R . . H3B H 0.2292 -0.0033 0.6395 0.052 Uiso 1 1 calc R . . C4 C 0.3386(3) 0.0078(3) 0.5692(3) 0.0484(12) Uani 1 1 d . . . H4A H 0.3702 0.0654 0.6275 0.058 Uiso 1 1 calc R . . H4B H 0.3679 -0.0451 0.5659 0.058 Uiso 1 1 calc R . . C5 C 0.3538(3) 0.0227(3) 0.4853(3) 0.0461(11) Uani 1 1 d . . . H5A H 0.4154 0.0088 0.4704 0.055 Uiso 1 1 calc R . . H5B H 0.3062 -0.0236 0.4306 0.055 Uiso 1 1 calc R . . C6 C 0.3084(3) 0.1854(3) 0.5632(3) 0.0299(9) Uani 1 1 d . . . C7 C 0.4038(3) 0.3135(3) 0.5521(3) 0.0353(9) Uani 1 1 d . . . H7A H 0.4664 0.3199 0.5854 0.042 Uiso 1 1 calc R . . H7B H 0.3965 0.3764 0.5597 0.042 Uiso 1 1 calc R . . C8 C 0.3932(3) 0.2431(3) 0.4471(3) 0.0407(10) Uani 1 1 d . . . H8A H 0.4404 0.2658 0.4189 0.049 Uiso 1 1 calc R . . H8B H 0.3307 0.2367 0.4135 0.049 Uiso 1 1 calc R . . C9 C 0.4067(3) 0.1471(3) 0.4394(3) 0.0457(11) Uani 1 1 d . . . H9A H 0.3888 0.0978 0.3729 0.055 Uiso 1 1 calc R . . H9B H 0.4733 0.1508 0.4603 0.055 Uiso 1 1 calc R . . C10 C 0.0960(3) 0.2094(3) 0.4903(3) 0.0293(9) Uani 1 1 d . . . C11 C 0.1223(3) 0.2695(3) 0.4522(3) 0.0379(10) Uani 1 1 d . . . H11 H 0.1641 0.3282 0.4897 0.046 Uiso 1 1 calc R . . C12 C 0.0856(3) 0.2415(4) 0.3566(3) 0.0495(12) Uani 1 1 d . . . H12 H 0.1038 0.2815 0.3302 0.059 Uiso 1 1 calc R . . C13 C 0.0235(3) 0.1563(4) 0.3019(3) 0.0556(14) Uani 1 1 d . . . H13 H -0.0007 0.1385 0.2385 0.067 Uiso 1 1 calc R . . C14 C -0.0040(3) 0.0959(4) 0.3403(3) 0.0491(12) Uani 1 1 d . . . H14 H -0.0464 0.0377 0.3026 0.059 Uiso 1 1 calc R . . C15 C 0.0315(3) 0.1222(3) 0.4343(3) 0.0392(10) Uani 1 1 d . . . H15 H 0.0127 0.0821 0.4604 0.047 Uiso 1 1 calc R . . C16 C 0.0566(3) 0.2199(3) 0.6710(2) 0.0311(9) Uani 1 1 d . . . C17 C -0.0370(3) 0.2215(3) 0.6428(3) 0.0409(11) Uani 1 1 d . . . H17 H -0.0535 0.2305 0.5898 0.049 Uiso 1 1 calc R . . C18 C -0.1057(3) 0.2098(4) 0.6930(3) 0.0510(12) Uani 1 1 d . . . H18 H -0.1683 0.2105 0.6733 0.061 Uiso 1 1 calc R . . C19 C -0.0825(4) 0.1971(4) 0.7722(4) 0.0587(14) Uani 1 1 d . . . H19 H -0.1293 0.1893 0.8056 0.070 Uiso 1 1 calc R . . C20 C 0.0097(4) 0.1960(4) 0.8017(3) 0.0580(14) Uani 1 1 d . . . H20 H 0.0255 0.1874 0.8551 0.070 Uiso 1 1 calc R . . C21 C 0.0800(3) 0.2079(3) 0.7511(3) 0.0450(11) Uani 1 1 d . . . H21 H 0.1426 0.2077 0.7713 0.054 Uiso 1 1 calc R . . C22 C 0.2778(3) 0.5821(3) 0.7936(3) 0.0305(9) Uani 1 1 d . . . H22 H 0.2753 0.5867 0.7341 0.037 Uiso 1 1 calc R . . C23 C 0.2582(3) 0.6768(3) 0.8702(3) 0.0410(10) Uani 1 1 d . . . H23A H 0.1903 0.6745 0.8625 0.049 Uiso 1 1 calc R . . H23B H 0.2793 0.6832 0.9331 0.049 Uiso 1 1 calc R . . C24 C 0.3078(3) 0.7653(3) 0.8652(3) 0.0521(12) Uani 1 1 d . . . H24A H 0.3061 0.8232 0.9234 0.063 Uiso 1 1 calc R . . H24B H 0.2743 0.7693 0.8115 0.063 Uiso 1 1 calc R . . C25 C 0.4127(3) 0.7593(4) 0.8531(3) 0.0552(13) Uani 1 1 d . . . H25A H 0.4141 0.7161 0.7867 0.066 Uiso 1 1 calc R . . H25B H 0.4472 0.8228 0.8686 0.066 Uiso 1 1 calc R . . C26 C 0.4619(3) 0.7243(3) 0.9156(3) 0.0533(13) Uani 1 1 d . . . H26A H 0.5297 0.7482 0.9266 0.064 Uiso 1 1 calc R . . H26B H 0.4417 0.7525 0.9772 0.064 Uiso 1 1 calc R . . C27 C 0.3714(2) 0.5548(3) 0.8121(2) 0.0266(8) Uani 1 1 d . . . C28 C 0.5260(3) 0.5899(3) 0.9128(3) 0.0446(12) Uani 1 1 d . . . H28A H 0.5423 0.6272 0.9820 0.054 Uiso 1 1 calc R . . H28B H 0.5806 0.6024 0.8862 0.054 Uiso 1 1 calc R . . C29 C 0.5026(3) 0.4854(3) 0.8847(3) 0.0434(11) Uani 1 1 d . . . H29A H 0.4585 0.4749 0.9228 0.052 Uiso 1 1 calc R . . H29B H 0.5598 0.4636 0.8967 0.052 Uiso 1 1 calc R . . C30 C 0.4591(3) 0.4288(3) 0.7806(3) 0.0328(9) Uani 1 1 d . . . H30A H 0.5039 0.4374 0.7422 0.039 Uiso 1 1 calc R . . H30B H 0.4435 0.3607 0.7624 0.039 Uiso 1 1 calc R . . C31 C 0.0788(3) 0.4894(3) 0.7212(2) 0.0313(9) Uani 1 1 d . . . C32 C 0.0747(3) 0.5298(3) 0.6608(3) 0.0422(11) Uani 1 1 d . . . H32 H 0.1305 0.5530 0.6470 0.051 Uiso 1 1 calc R . . C33 C -0.0119(3) 0.5363(4) 0.6205(3) 0.0505(13) Uani 1 1 d . . . H33 H -0.0136 0.5655 0.5812 0.061 Uiso 1 1 calc R . . C34 C -0.0953(3) 0.5001(4) 0.6379(3) 0.0500(13) Uani 1 1 d . . . H34 H -0.1533 0.5039 0.6099 0.060 Uiso 1 1 calc R . . C35 C -0.0925(3) 0.4581(4) 0.6971(3) 0.0457(12) Uani 1 1 d . . . H35 H -0.1488 0.4331 0.7088 0.055 Uiso 1 1 calc R . . C36 C -0.0064(3) 0.4529(3) 0.7391(3) 0.0375(10) Uani 1 1 d . . . H36 H -0.0050 0.4250 0.7796 0.045 Uiso 1 1 calc R . . C37 C 0.1811(2) 0.4786(3) 0.8834(2) 0.0291(9) Uani 1 1 d . . . C38 C 0.2273(3) 0.4192(3) 0.9082(3) 0.0375(10) Uani 1 1 d . . . H38 H 0.2617 0.3788 0.8662 0.045 Uiso 1 1 calc R . . C39 C 0.2223(3) 0.4196(4) 0.9943(3) 0.0482(12) Uani 1 1 d . . . H39 H 0.2540 0.3803 1.0109 0.058 Uiso 1 1 calc R . . C40 C 0.1700(3) 0.4786(4) 1.0561(3) 0.0522(13) Uani 1 1 d . . . H40 H 0.1650 0.4777 1.1135 0.063 Uiso 1 1 calc R . . C41 C 0.1255(3) 0.5385(4) 1.0327(3) 0.0484(12) Uani 1 1 d . . . H41 H 0.0921 0.5794 1.0756 0.058 Uiso 1 1 calc R . . C42 C 0.1295(3) 0.5391(3) 0.9473(3) 0.0385(10) Uani 1 1 d . . . H42 H 0.0982 0.5793 0.9318 0.046 Uiso 1 1 calc R . . C43 C 0.2950(4) 0.0743(4) 0.9124(3) 0.0708(17) Uani 1 1 d . A 1 H43 H 0.3126 0.1126 0.8802 0.085 Uiso 1 1 calc R A 1 C44 C 0.2861(3) 0.7214(4) 0.5645(3) 0.0549(13) Uani 1 1 d . . . H44 H 0.2930 0.6578 0.5571 0.066 Uiso 1 1 calc R . . C45 C 0.3578(3) 0.4045(4) 0.3316(3) 0.0519(12) Uani 1 1 d . . . H45 H 0.3310 0.4169 0.3894 0.062 Uiso 1 1 calc R . . C46 C 0.5724(3) 0.2073(4) 0.7877(3) 0.0499(12) Uani 1 1 d . . . H46 H 0.5127 0.2245 0.8080 0.060 Uiso 1 1 calc R . . C47 C 0.1906(6) 0.9922(7) 1.1604(6) 0.1524(14) Uiso 1 1 d D . . H47A H 0.1523 0.9811 1.2018 0.229 Uiso 1 1 calc R . . H47B H 0.2137 1.0602 1.1862 0.229 Uiso 1 1 calc R . . H47C H 0.2433 0.9602 1.1559 0.229 Uiso 1 1 calc R . . C48 C 0.1320(6) 0.9533(6) 1.0628(6) 0.1524(14) Uiso 1 1 d D . . H48A H 0.0883 0.9956 1.0650 0.183 Uiso 1 1 calc R . . H48B H 0.1735 0.9535 1.0185 0.183 Uiso 1 1 calc R . . C49 C 0.0202(6) 0.8187(7) 0.9324(5) 0.1524(14) Uiso 1 1 d D . . H49A H 0.0615 0.8149 0.8869 0.183 Uiso 1 1 calc R . . H49B H -0.0205 0.8636 0.9349 0.183 Uiso 1 1 calc R . . C50 C -0.0398(6) 0.7205(6) 0.8997(6) 0.1524(14) Uiso 1 1 d D . . H50A H 0.0006 0.6758 0.8961 0.229 Uiso 1 1 calc R . . H50B H -0.0773 0.6986 0.8376 0.229 Uiso 1 1 calc R . . H50C H -0.0810 0.7244 0.9446 0.229 Uiso 1 1 calc R . . O1 O 0.0770(5) 0.8535(5) 1.0262(4) 0.1524(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0225(2) 0.0216(3) 0.0296(3) 0.0085(2) 0.00373(19) 0.0012(2) P1 0.0251(5) 0.0244(6) 0.0304(5) 0.0122(4) 0.0036(4) 0.0003(4) P2 0.0248(5) 0.0268(6) 0.0266(5) 0.0110(4) 0.0037(4) 0.0045(4) N1 0.0236(15) 0.0220(18) 0.0321(16) 0.0126(14) 0.0075(12) 0.0020(13) N2 0.044(2) 0.0247(19) 0.0395(18) 0.0153(16) 0.0139(15) 0.0118(16) N3 0.0239(16) 0.029(2) 0.0303(16) 0.0153(15) 0.0038(13) 0.0033(14) N4 0.0333(18) 0.027(2) 0.0349(17) 0.0092(15) -0.0012(14) -0.0034(15) Cl1 0.0449(6) 0.0384(7) 0.0427(6) 0.0203(5) 0.0028(5) 0.0058(5) Cl2 0.0378(5) 0.0391(6) 0.0374(5) 0.0190(5) 0.0082(4) 0.0097(5) Cl3A 0.077(3) 0.048(3) 0.112(4) 0.031(3) -0.016(3) 0.003(2) Cl4A 0.097(4) 0.081(4) 0.068(3) 0.009(2) 0.038(3) -0.008(4) Cl5A 0.064(6) 0.080(6) 0.073(5) 0.021(4) -0.003(3) -0.011(4) Cl4B 0.165(7) 0.106(5) 0.121(6) 0.059(4) 0.081(5) 0.052(6) Cl3B 0.091(6) 0.065(5) 0.126(7) 0.059(5) -0.051(5) -0.023(4) Cl5B 0.055(5) 0.045(3) 0.043(3) 0.014(3) -0.011(4) 0.000(4) Cl22 0.067(6) 0.079(7) 0.053(4) 0.030(4) -0.009(4) -0.021(5) Cl20 0.094(6) 0.093(6) 0.113(6) 0.059(5) 0.033(5) 0.020(5) Cl21 0.115(9) 0.061(6) 0.079(6) 0.038(4) 0.015(7) 0.031(7) Cl6 0.0614(8) 0.1212(15) 0.0680(8) 0.0595(9) 0.0075(7) 0.0069(9) Cl7 0.0555(8) 0.0621(9) 0.0824(9) 0.0344(7) 0.0230(7) 0.0162(7) Cl8 0.0872(10) 0.0579(9) 0.0542(7) 0.0193(7) 0.0197(7) -0.0051(8) Cl9 0.0592(9) 0.1193(15) 0.1444(14) 0.0961(13) 0.0546(9) 0.0493(9) Cl10 0.0489(7) 0.0468(7) 0.0596(7) 0.0276(6) 0.0157(5) 0.0081(6) Cl11 0.1008(12) 0.0747(12) 0.0638(9) 0.0227(8) -0.0168(8) -0.0237(9) Cl12 0.1663(18) 0.0722(12) 0.0950(11) 0.0495(10) 0.0422(12) 0.0544(13) Cl13 0.0780(9) 0.0713(10) 0.0484(7) 0.0281(7) 0.0171(6) 0.0244(8) Cl14 0.0774(10) 0.0948(13) 0.0736(10) 0.0230(9) -0.0204(8) -0.0046(9) C1 0.032(2) 0.025(2) 0.0316(19) 0.0127(17) 0.0047(16) -0.0015(17) C2 0.043(2) 0.028(2) 0.045(2) 0.019(2) 0.0032(19) -0.0030(19) C3 0.051(3) 0.025(2) 0.052(3) 0.018(2) 0.006(2) 0.003(2) C4 0.053(3) 0.028(3) 0.069(3) 0.028(2) 0.004(2) 0.009(2) C5 0.046(3) 0.030(3) 0.059(3) 0.016(2) 0.017(2) 0.014(2) C6 0.028(2) 0.027(2) 0.033(2) 0.0140(18) -0.0004(16) 0.0047(17) C7 0.033(2) 0.030(2) 0.047(2) 0.0189(19) 0.0159(18) 0.0074(18) C8 0.049(3) 0.039(3) 0.043(2) 0.023(2) 0.022(2) 0.013(2) C9 0.050(3) 0.039(3) 0.046(2) 0.015(2) 0.023(2) 0.008(2) C10 0.027(2) 0.026(2) 0.035(2) 0.0143(18) 0.0079(16) 0.0047(17) C11 0.038(2) 0.031(3) 0.044(2) 0.019(2) 0.0072(18) 0.0036(19) C12 0.056(3) 0.059(3) 0.047(3) 0.037(3) 0.012(2) 0.010(3) C13 0.062(3) 0.067(4) 0.033(2) 0.023(2) 0.000(2) 0.006(3) C14 0.050(3) 0.044(3) 0.040(2) 0.014(2) -0.007(2) 0.001(2) C15 0.034(2) 0.040(3) 0.037(2) 0.017(2) -0.0015(18) -0.002(2) C16 0.033(2) 0.025(2) 0.030(2) 0.0108(17) 0.0071(16) -0.0020(17) C17 0.035(2) 0.043(3) 0.043(2) 0.019(2) 0.0120(18) 0.004(2) C18 0.033(2) 0.056(3) 0.062(3) 0.027(3) 0.012(2) 0.003(2) C19 0.050(3) 0.061(4) 0.066(3) 0.030(3) 0.030(2) -0.002(3) C20 0.055(3) 0.070(4) 0.050(3) 0.031(3) 0.016(2) 0.001(3) C21 0.041(2) 0.047(3) 0.048(2) 0.027(2) 0.006(2) -0.003(2) C22 0.033(2) 0.024(2) 0.035(2) 0.0143(17) 0.0059(16) 0.0040(17) C23 0.046(2) 0.033(3) 0.040(2) 0.014(2) 0.0104(19) 0.010(2) C24 0.066(3) 0.026(3) 0.060(3) 0.018(2) 0.007(2) 0.006(2) C25 0.061(3) 0.037(3) 0.064(3) 0.026(2) 0.006(2) -0.008(2) C26 0.048(3) 0.032(3) 0.060(3) 0.011(2) -0.003(2) -0.004(2) C27 0.0277(19) 0.027(2) 0.0234(18) 0.0116(17) 0.0032(15) 0.0005(16) C28 0.035(2) 0.055(3) 0.033(2) 0.016(2) -0.0022(17) 0.000(2) C29 0.038(2) 0.051(3) 0.042(2) 0.026(2) -0.0050(19) 0.005(2) C30 0.029(2) 0.034(2) 0.038(2) 0.0198(19) 0.0027(16) 0.0065(18) C31 0.031(2) 0.033(2) 0.0276(19) 0.0103(17) 0.0060(16) 0.0104(18) C32 0.040(2) 0.056(3) 0.041(2) 0.028(2) 0.0139(19) 0.015(2) C33 0.048(3) 0.077(4) 0.041(2) 0.035(3) 0.008(2) 0.027(3) C34 0.037(2) 0.074(4) 0.034(2) 0.019(2) 0.0012(18) 0.024(2) C35 0.030(2) 0.061(3) 0.039(2) 0.017(2) 0.0041(18) 0.011(2) C36 0.035(2) 0.042(3) 0.033(2) 0.0150(19) 0.0041(17) 0.008(2) C37 0.0247(19) 0.029(2) 0.0302(19) 0.0128(17) 0.0024(15) 0.0018(17) C38 0.034(2) 0.043(3) 0.038(2) 0.021(2) 0.0038(17) 0.006(2) C39 0.044(3) 0.061(3) 0.047(3) 0.037(2) -0.004(2) -0.001(2) C40 0.046(3) 0.074(4) 0.036(2) 0.029(3) 0.007(2) -0.001(3) C41 0.044(3) 0.059(3) 0.036(2) 0.017(2) 0.0129(19) 0.007(2) C42 0.030(2) 0.048(3) 0.036(2) 0.018(2) 0.0079(17) 0.008(2) C43 0.110(5) 0.047(3) 0.048(3) 0.024(3) 0.000(3) -0.004(3) C44 0.061(3) 0.050(3) 0.074(3) 0.042(3) 0.026(3) 0.015(3) C45 0.044(3) 0.056(3) 0.056(3) 0.026(2) 0.015(2) 0.001(2) C46 0.051(3) 0.052(3) 0.047(3) 0.021(2) 0.009(2) 0.019(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 N3 1.923(3) . ? Ni1 N1 1.934(3) . ? Ni1 P2 2.1266(11) . ? Ni1 P1 2.1360(11) . ? P1 C16 1.815(4) . ? P1 C10 1.819(4) . ? P1 C1 1.854(4) . ? P2 C31 1.805(4) . ? P2 C37 1.822(4) . ? P2 C22 1.832(4) . ? N1 C6 1.302(5) . ? N1 C7 1.479(5) . ? N2 C6 1.356(5) . ? N2 C9 1.458(5) . ? N2 C5 1.474(6) . ? N3 C27 1.312(5) . ? N3 C30 1.470(5) . ? N4 C27 1.347(5) . ? N4 C26 1.457(6) . ? N4 C28 1.464(5) . ? Cl3A C43 1.892(9) . ? Cl4A C43 1.605(8) . ? Cl5A C43 1.721(15) . ? Cl6 C44 1.778(5) . ? Cl7 C44 1.747(5) . ? Cl8 C44 1.760(5) . ? Cl9 C45 1.771(5) . ? Cl10 C45 1.749(5) . ? Cl11 C45 1.737(5) . ? Cl12 C46 1.745(5) . ? Cl13 C46 1.751(5) . ? Cl14 C46 1.748(5) . ? C1 C6 1.521(5) . ? C1 C2 1.524(5) . ? C1 H1 0.9800 . ? C2 C3 1.525(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.523(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.490(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.508(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.509(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.376(6) . ? C10 C15 1.398(6) . ? C11 C12 1.398(6) . ? C11 H11 0.9300 . ? C12 C13 1.361(7) . ? C12 H12 0.9300 . ? C13 C14 1.388(7) . ? C13 H13 0.9300 . ? C14 C15 1.378(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.385(5) . ? C16 C17 1.388(5) . ? C17 C18 1.378(6) . ? C17 H17 0.9300 . ? C18 C19 1.378(7) . ? C18 H18 0.9300 . ? C19 C20 1.371(7) . ? C19 H19 0.9300 . ? C20 C21 1.403(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C27 1.513(5) . ? C22 C23 1.531(5) . ? C22 H22 0.9800 . ? C23 C24 1.529(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.556(7) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.502(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C28 C29 1.488(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.497(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.374(6) . ? C31 C36 1.403(6) . ? C32 C33 1.386(6) . ? C32 H32 0.9300 . ? C33 C34 1.374(7) . ? C33 H33 0.9300 . ? C34 C35 1.378(7) . ? C34 H34 0.9300 . ? C35 C36 1.381(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.390(5) . ? C37 C42 1.402(5) . ? C38 C39 1.376(5) . ? C38 H38 0.9300 . ? C39 C40 1.383(7) . ? C39 H39 0.9300 . ? C40 C41 1.372(7) . ? C40 H40 0.9300 . ? C41 C42 1.369(6) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 H43 0.9800 . ? C44 H44 0.9800 . ? C45 H45 0.9800 . ? C46 H46 0.9800 . ? C47 C48 1.497(12) . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C48 O1 1.490(13) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 O1 1.447(5) . ? C49 C50 1.507(15) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 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 N3 Ni1 N1 96.52(13) . . ? N3 Ni1 P2 81.99(9) . . ? N1 Ni1 P2 173.11(10) . . ? N3 Ni1 P1 164.69(10) . . ? N1 Ni1 P1 81.43(9) . . ? P2 Ni1 P1 101.77(4) . . ? C16 P1 C10 106.99(17) . . ? C16 P1 C1 105.13(18) . . ? C10 P1 C1 106.88(17) . . ? C16 P1 Ni1 123.03(13) . . ? C10 P1 Ni1 116.48(14) . . ? C1 P1 Ni1 95.87(12) . . ? C31 P2 C37 107.53(17) . . ? C31 P2 C22 106.10(19) . . ? C37 P2 C22 106.70(17) . . ? C31 P2 Ni1 121.49(12) . . ? C37 P2 Ni1 114.40(13) . . ? C22 P2 Ni1 99.00(12) . . ? C6 N1 C7 118.1(3) . . ? C6 N1 Ni1 121.7(3) . . ? C7 N1 Ni1 119.9(3) . . ? C6 N2 C9 120.5(4) . . ? C6 N2 C5 125.4(3) . . ? C9 N2 C5 113.7(3) . . ? C27 N3 C30 118.4(3) . . ? C27 N3 Ni1 123.4(2) . . ? C30 N3 Ni1 117.7(3) . . ? C27 N4 C26 126.8(3) . . ? C27 N4 C28 121.3(4) . . ? C26 N4 C28 111.5(3) . . ? C6 C1 C2 117.6(3) . . ? C6 C1 P1 101.4(3) . . ? C2 C1 P1 116.0(3) . . ? C6 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? P1 C1 H1 107.0 . . ? C3 C2 C1 111.6(3) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 111.5(4) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 113.6(4) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? N2 C5 C4 115.7(4) . . ? N2 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? N2 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N1 C6 N2 123.6(4) . . ? N1 C6 C1 114.8(3) . . ? N2 C6 C1 121.5(4) . . ? N1 C7 C8 109.2(3) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C7 C8 C9 107.7(3) . . ? C7 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? C7 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N2 C9 C8 111.6(3) . . ? N2 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? N2 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C15 120.1(4) . . ? C11 C10 P1 118.9(3) . . ? C15 C10 P1 120.9(3) . . ? C10 C11 C12 119.4(4) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.3(4) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 119.6(4) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? C21 C16 C17 119.0(4) . . ? C21 C16 P1 118.9(3) . . ? C17 C16 P1 121.9(3) . . ? C18 C17 C16 120.3(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.7(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.7(5) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C16 C21 C20 120.3(4) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C27 C22 C23 117.6(3) . . ? C27 C22 P2 102.6(3) . . ? C23 C22 P2 114.4(3) . . ? C27 C22 H22 107.2 . . ? C23 C22 H22 107.2 . . ? P2 C22 H22 107.2 . . ? C24 C23 C22 112.8(4) . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? C22 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C23 C24 C25 110.8(4) . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C26 C25 C24 113.0(4) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? N4 C26 C25 115.7(4) . . ? N4 C26 H26A 108.4 . . ? C25 C26 H26A 108.4 . . ? N4 C26 H26B 108.4 . . ? C25 C26 H26B 108.4 . . ? H26A C26 H26B 107.4 . . ? N3 C27 N4 123.2(3) . . ? N3 C27 C22 114.8(3) . . ? N4 C27 C22 121.9(3) . . ? N4 C28 C29 110.6(3) . . ? N4 C28 H28A 109.5 . . ? C29 C28 H28A 109.5 . . ? N4 C28 H28B 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 108.1 . . ? C28 C29 C30 109.9(4) . . ? C28 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? C28 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? N3 C30 C29 109.2(3) . . ? N3 C30 H30A 109.8 . . ? C29 C30 H30A 109.8 . . ? N3 C30 H30B 109.8 . . ? C29 C30 H30B 109.8 . . ? H30A C30 H30B 108.3 . . ? C32 C31 C36 118.6(4) . . ? C32 C31 P2 120.6(3) . . ? C36 C31 P2 120.6(3) . . ? C31 C32 C33 120.6(4) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 120.7(4) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.5(4) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C34 C35 C36 120.2(4) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C31 120.4(4) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? C38 C37 C42 119.2(4) . . ? C38 C37 P2 118.1(3) . . ? C42 C37 P2 122.7(3) . . ? C39 C38 C37 120.4(4) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C38 C39 C40 119.8(4) . . ? C38 C39 H39 120.1 . . ? C40 C39 H39 120.1 . . ? C41 C40 C39 120.1(4) . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C42 C41 C40 121.0(4) . . ? C42 C41 H41 119.5 . . ? C40 C41 H41 119.5 . . ? C41 C42 C37 119.5(4) . . ? C41 C42 H42 120.3 . . ? C37 C42 H42 120.3 . . ? Cl4A C43 Cl5A 117.1(6) . . ? Cl4A C43 Cl3A 110.5(4) . . ? Cl5A C43 Cl3A 109.3(6) . . ? Cl4A C43 H43 106.4 . . ? Cl5A C43 H43 106.4 . . ? Cl3A C43 H43 106.4 . . ? Cl7 C44 Cl8 110.5(3) . . ? Cl7 C44 Cl6 110.1(3) . . ? Cl8 C44 Cl6 108.0(3) . . ? Cl7 C44 H44 109.4 . . ? Cl8 C44 H44 109.4 . . ? Cl6 C44 H44 109.4 . . ? Cl11 C45 Cl10 111.3(3) . . ? Cl11 C45 Cl9 108.8(3) . . ? Cl10 C45 Cl9 110.5(3) . . ? Cl11 C45 H45 108.8 . . ? Cl10 C45 H45 108.8 . . ? Cl9 C45 H45 108.8 . . ? Cl12 C46 Cl14 110.6(3) . . ? Cl12 C46 Cl13 110.0(3) . . ? Cl14 C46 Cl13 109.9(3) . . ? Cl12 C46 H46 108.8 . . ? Cl14 C46 H46 108.8 . . ? Cl13 C46 H46 108.8 . . ? C48 C47 H47A 109.5 . . ? C48 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C48 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? O1 C48 C47 112.8(7) . . ? O1 C48 H48A 109.0 . . ? C47 C48 H48A 109.0 . . ? O1 C48 H48B 109.0 . . ? C47 C48 H48B 109.0 . . ? H48A C48 H48B 107.8 . . ? O1 C49 C50 110.6(7) . . ? O1 C49 H49A 109.5 . . ? C50 C49 H49A 109.5 . . ? O1 C49 H49B 109.5 . . ? C50 C49 H49B 109.5 . . ? H49A C49 H49B 108.1 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C49 O1 C48 111.4(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.485 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.134 # Attachment 'compound4_revised.cif' data_4.6H2O _database_code_depnum_ccdc_archive 'CCDC 724932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H50 N4 Ni P2, 2(Br), 6(H2 O)' _chemical_formula_sum 'C42 H62 Br2 N4 Ni O6 P2' _chemical_formula_weight 999.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.3393 1.1124 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9492(3) _cell_length_b 15.0496(5) _cell_length_c 25.3293(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.227(2) _cell_angle_gamma 90.00 _cell_volume 4554.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 27207 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2072 _exptl_absorpt_coefficient_mu 2.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details 'L. Spek, J. Appl.Cryst. 2003, 36, 7, B. Blessing, Acta Cryst, 1995, A51, 33' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24227 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.49 _reflns_number_total 10110 _reflns_number_gt 6827 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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. A severe disorder involed both phosphines. The P1 seven-membered cycle was disordered in two positions with occupancy factors 0.3/0.7. The P2 seven-membered cycle was disordered in two positions having equal occupancy factors. Atoms C1A, C1B, C3A, C3B, C24A and C24B were refined isotropically. Several distances in the disordered moieties were restrained to match the appropriate geometry, namely distances C23-C24A, C23-C24B, C26B-C25B, C24B-C25B and C24A-C25A and angular distances C3A...C5 and C3B...C5. The deviation of the N4-C26(A and B) distances from the ideal ones is probably due to an additional disorder concerning the C7-C8-C9-N2 atoms, which could not be resolved. ; _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^)+(0.0759P)^2^+14.7638P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10110 _refine_ls_number_parameters 538 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1775 _refine_ls_wR_factor_gt 0.1576 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.023 _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 0.24418(5) 0.28676(4) 0.13618(2) 0.02411(17) Uani 1 1 d . A . P1 P 0.23873(11) 0.22113(8) 0.21046(5) 0.0255(3) Uani 1 1 d . . . P2 P 0.34064(10) 0.40027(8) 0.15628(5) 0.0230(3) Uani 1 1 d . . . N1 N 0.1422(3) 0.1914(3) 0.11821(16) 0.0280(9) Uani 1 1 d . . . N2 N 0.0778(4) 0.0465(3) 0.13161(18) 0.0370(11) Uani 1 1 d . . . N3 N 0.2695(3) 0.3307(3) 0.06575(15) 0.0267(9) Uani 1 1 d . . . N4 N 0.3050(4) 0.4474(4) 0.00687(17) 0.0437(12) Uani 1 1 d . . . C1A C 0.2460(6) 0.1077(5) 0.1797(3) 0.0223(14) Uiso 0.70 1 d P A 1 H1A H 0.3154 0.1033 0.1593 0.027 Uiso 0.70 1 calc PR A 1 C1B C 0.2137(14) 0.1024(11) 0.1948(7) 0.0223(14) Uiso 0.30 1 d P A 2 H1B H 0.1687 0.0728 0.2218 0.027 Uiso 0.30 1 calc PR A 2 C2A C 0.2430(6) 0.0337(5) 0.2188(3) 0.0310(16) Uani 0.70 1 d P A 1 H2A1 H 0.1669 0.0255 0.2311 0.037 Uiso 0.70 1 calc PR A 1 H2A2 H 0.2894 0.0488 0.2490 0.037 Uiso 0.70 1 calc PR A 1 C2B C 0.3212(14) 0.0501(11) 0.1818(7) 0.032(4) Uani 0.30 1 d P A 2 H2B1 H 0.3457 0.0649 0.1464 0.038 Uiso 0.30 1 calc PR A 2 H2B2 H 0.3802 0.0671 0.2063 0.038 Uiso 0.30 1 calc PR A 2 C3B C 0.3019(12) -0.0458(19) 0.1856(7) 0.0414(19) Uiso 0.30 1 d PD A 2 H3B1 H 0.2697 -0.0602 0.2196 0.050 Uiso 0.30 1 calc PR A 2 H3B2 H 0.3723 -0.0774 0.1823 0.050 Uiso 0.30 1 calc PR A 2 C4 C 0.2220(5) -0.0739(4) 0.1413(2) 0.0431(14) Uani 1 1 d D . . H4A H 0.2572 -0.0413 0.1128 0.052 Uiso 1 1 calc R A 1 H4B H 0.2271 -0.1367 0.1332 0.052 Uiso 1 1 calc R A 1 C6 C 0.1473(4) 0.1141(3) 0.1411(2) 0.0317(11) Uani 1 1 d . A . C7 C 0.0493(4) 0.2087(4) 0.0813(2) 0.0354(12) Uani 1 1 d . A . H7A H 0.0710 0.1911 0.0459 0.042 Uiso 1 1 calc R . . H7B H 0.0327 0.2717 0.0808 0.042 Uiso 1 1 calc R . . C8 C -0.0535(5) 0.1578(4) 0.0974(2) 0.0357(12) Uani 1 1 d . . . H8A H -0.1138 0.1679 0.0724 0.043 Uiso 1 1 calc R A . H8B H -0.0781 0.1768 0.1321 0.043 Uiso 1 1 calc R . . C9 C -0.0214(4) 0.0593(4) 0.0984(2) 0.0362(12) Uani 1 1 d . A . H9A H -0.0831 0.0245 0.1121 0.043 Uiso 1 1 calc R . . H9B H -0.0059 0.0392 0.0628 0.043 Uiso 1 1 calc R . . C10 C 0.1084(4) 0.2325(3) 0.24583(19) 0.0289(11) Uani 1 1 d . A . C11 C 0.0252(4) 0.2850(4) 0.2243(2) 0.0333(11) Uani 1 1 d . . . H11 H 0.0397 0.3188 0.1944 0.040 Uiso 1 1 calc R A . C12 C -0.0799(5) 0.2876(4) 0.2472(2) 0.0445(14) Uani 1 1 d . A . H12 H -0.1362 0.3221 0.2321 0.053 Uiso 1 1 calc R . . C13 C -0.1014(5) 0.2392(4) 0.2922(2) 0.0471(15) Uani 1 1 d . . . H13 H -0.1722 0.2413 0.3073 0.056 Uiso 1 1 calc R A . C14 C -0.0181(5) 0.1873(4) 0.3152(2) 0.0451(15) Uani 1 1 d . A . H14 H -0.0326 0.1554 0.3459 0.054 Uiso 1 1 calc R . . C15 C 0.0867(5) 0.1835(4) 0.2920(2) 0.0370(13) Uani 1 1 d . . . H15 H 0.1426 0.1485 0.3069 0.044 Uiso 1 1 calc R A . C16 C 0.3538(4) 0.2267(3) 0.25713(19) 0.0284(11) Uani 1 1 d . A . C17 C 0.3410(5) 0.2661(4) 0.3065(2) 0.0428(14) Uani 1 1 d . . . H17 H 0.2712 0.2861 0.3174 0.051 Uiso 1 1 calc R A . C18 C 0.4340(6) 0.2752(4) 0.3394(2) 0.0477(16) Uani 1 1 d . A . H18 H 0.4260 0.3005 0.3727 0.057 Uiso 1 1 calc R . . C19 C 0.5372(5) 0.2472(4) 0.3228(2) 0.0479(16) Uani 1 1 d . . . H19 H 0.5989 0.2543 0.3449 0.057 Uiso 1 1 calc R A . C20 C 0.5507(5) 0.2084(4) 0.2740(3) 0.0492(16) Uani 1 1 d . A . H20 H 0.6207 0.1884 0.2633 0.059 Uiso 1 1 calc R . . C21 C 0.4593(5) 0.1996(4) 0.2410(2) 0.0374(13) Uani 1 1 d . . . H21 H 0.4684 0.1752 0.2076 0.045 Uiso 1 1 calc R A . C22 C 0.2940(4) 0.4746(3) 0.10333(18) 0.0293(11) Uani 1 1 d D A . H22 H 0.2178 0.4941 0.1117 0.035 Uiso 1 1 calc R . . C23 C 0.3673(5) 0.5584(4) 0.0975(2) 0.0409(14) Uani 1 1 d D . . H23A H 0.3827 0.5799 0.1329 0.049 Uiso 1 1 calc R A 1 H23B H 0.4383 0.5390 0.0830 0.049 Uiso 1 1 calc R A 1 C24B C 0.3306(15) 0.6362(7) 0.0659(4) 0.052(5) Uiso 0.50 1 d PD A 1 H24A H 0.3824 0.6847 0.0720 0.062 Uiso 0.50 1 calc PR A 1 H24B H 0.2576 0.6551 0.0783 0.062 Uiso 0.50 1 calc PR A 1 C25A C 0.2415(10) 0.6002(9) 0.0205(4) 0.041(3) Uani 0.50 1 d PD A 2 H25A H 0.1723 0.5720 0.0314 0.049 Uiso 0.50 1 calc PR A 2 H25B H 0.2218 0.6498 -0.0022 0.049 Uiso 0.50 1 calc PR A 2 C25B C 0.3232(12) 0.6192(9) 0.0069(4) 0.055(3) Uani 0.50 1 d PD A 1 H25C H 0.2969 0.6721 -0.0112 0.066 Uiso 0.50 1 calc PR A 1 H25D H 0.3965 0.6042 -0.0068 0.066 Uiso 0.50 1 calc PR A 1 C24A C 0.2991(11) 0.6370(4) 0.0695(4) 0.039(4) Uiso 0.50 1 d PD A 2 H24C H 0.2439 0.6609 0.0937 0.047 Uiso 0.50 1 calc PR A 2 H24D H 0.3498 0.6846 0.0598 0.047 Uiso 0.50 1 calc PR A 2 C26A C 0.3076(15) 0.5339(9) -0.0119(5) 0.045(3) Uani 0.50 1 d P A 2 H26A H 0.2787 0.5343 -0.0477 0.054 Uiso 0.50 1 calc PR A 2 H26B H 0.3849 0.5533 -0.0132 0.054 Uiso 0.50 1 calc PR A 2 C26B C 0.2432(12) 0.5437(9) -0.0026(6) 0.041(3) Uani 0.50 1 d PD A 1 H26C H 0.2150 0.5467 -0.0386 0.049 Uiso 0.50 1 calc PR A 1 H26D H 0.1801 0.5491 0.0211 0.049 Uiso 0.50 1 calc PR A 1 C27 C 0.2874(4) 0.4146(4) 0.05551(18) 0.0274(11) Uani 1 1 d . A . C28 C 0.2715(5) 0.2673(4) 0.0215(2) 0.0365(13) Uani 1 1 d . A . H28A H 0.1978 0.2635 0.0055 0.044 Uiso 1 1 calc R . . H28B H 0.2920 0.2087 0.0343 0.044 Uiso 1 1 calc R . . C29 C 0.3562(5) 0.2983(5) -0.0194(3) 0.059(2) Uani 1 1 d . . . H29A H 0.4304 0.3011 -0.0038 0.071 Uiso 1 1 calc R A . H29B H 0.3581 0.2571 -0.0488 0.071 Uiso 1 1 calc R . . C30 C 0.3210(6) 0.3885(5) -0.0380(2) 0.0574(19) Uani 1 1 d . A . H30A H 0.3779 0.4128 -0.0611 0.069 Uiso 1 1 calc R . . H30B H 0.2518 0.3838 -0.0580 0.069 Uiso 1 1 calc R . . C31 C 0.3168(4) 0.4589(3) 0.21753(18) 0.0254(10) Uani 1 1 d . A . C32 C 0.2139(4) 0.4992(4) 0.2256(2) 0.0323(11) Uani 1 1 d . . . H32 H 0.1594 0.4973 0.1993 0.039 Uiso 1 1 calc R A . C33 C 0.1919(5) 0.5422(4) 0.2728(2) 0.0429(14) Uani 1 1 d . A . H33 H 0.1229 0.5694 0.2779 0.052 Uiso 1 1 calc R . . C34 C 0.2728(5) 0.5447(4) 0.3124(2) 0.0403(13) Uani 1 1 d . . . H34 H 0.2588 0.5750 0.3437 0.048 Uiso 1 1 calc R A . C35 C 0.3727(5) 0.5025(4) 0.3053(2) 0.0375(13) Uani 1 1 d . A . H35 H 0.4258 0.5028 0.3322 0.045 Uiso 1 1 calc R . . C36 C 0.3957(4) 0.4591(4) 0.25820(19) 0.0326(12) Uani 1 1 d . . . H36 H 0.4639 0.4302 0.2538 0.039 Uiso 1 1 calc R A . C37 C 0.4898(4) 0.3839(4) 0.14822(18) 0.0283(11) Uani 1 1 d . A . C38 C 0.5705(4) 0.4469(4) 0.1618(2) 0.0337(12) Uani 1 1 d . . . H38 H 0.5490 0.5010 0.1764 0.040 Uiso 1 1 calc R A . C39 C 0.6840(5) 0.4288(4) 0.1534(2) 0.0402(14) Uani 1 1 d . A . H39 H 0.7377 0.4709 0.1624 0.048 Uiso 1 1 calc R . . C40 C 0.7159(5) 0.3494(4) 0.1320(2) 0.0419(14) Uani 1 1 d . . . H40 H 0.7916 0.3374 0.1274 0.050 Uiso 1 1 calc R A . C41 C 0.6381(5) 0.2873(4) 0.1174(2) 0.0414(14) Uani 1 1 d . A . H41 H 0.6606 0.2342 0.1019 0.050 Uiso 1 1 calc R . . C42 C 0.5254(4) 0.3041(4) 0.1258(2) 0.0323(11) Uani 1 1 d . . . H42 H 0.4727 0.2614 0.1163 0.039 Uiso 1 1 calc R A . Br1 Br -0.01069(5) 0.46356(4) 0.10850(2) 0.04014(18) Uani 1 1 d . . . Br2 Br 0.46637(7) 0.07934(5) 0.07322(3) 0.0594(2) Uani 1 1 d . . . O1 O 0.8254(4) -0.1507(4) 0.0983(2) 0.0716(14) Uani 1 1 d . . . O2 O 0.7803(5) 0.1408(4) -0.0101(2) 0.0839(18) Uani 1 1 d . B 1 O3 O 0.4392(4) -0.1397(3) 0.04796(19) 0.0648(13) Uani 1 1 d . . . O4 O 0.2916(6) 0.0286(4) -0.0305(2) 0.096(2) Uani 1 1 d . . . O5 O -0.0402(4) 0.6193(3) 0.01499(17) 0.0522(11) Uani 1 1 d . . . O6 O 0.0280(5) 0.7827(4) 0.0551(2) 0.0713(15) Uani 1 1 d . . . C5 C 0.1003(5) -0.0476(4) 0.1445(3) 0.0512(17) Uani 1 1 d D A . H5A1 H 0.0577 -0.0848 0.1205 0.061 Uiso 1 1 calc R . . H5A2 H 0.0738 -0.0594 0.1800 0.061 Uiso 1 1 calc R . . C3A C 0.2863(6) -0.0551(8) 0.1934(3) 0.0414(19) Uiso 0.70 1 d PD A 1 H3A1 H 0.3658 -0.0503 0.1862 0.050 Uiso 0.70 1 calc PR A 1 H3A2 H 0.2753 -0.1039 0.2178 0.050 Uiso 0.70 1 calc PR A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0244(3) 0.0265(3) 0.0214(3) -0.0023(3) -0.0033(2) -0.0027(3) P1 0.0288(6) 0.0221(6) 0.0257(6) 0.0009(5) -0.0074(5) -0.0009(5) P2 0.0213(6) 0.0265(6) 0.0213(6) 0.0009(5) -0.0030(4) -0.0023(5) N1 0.027(2) 0.026(2) 0.031(2) -0.0027(18) -0.0089(17) -0.0022(17) N2 0.041(3) 0.025(2) 0.046(3) -0.004(2) -0.017(2) -0.001(2) N3 0.027(2) 0.031(2) 0.0213(19) -0.0054(18) -0.0008(16) 0.0017(18) N4 0.050(3) 0.055(3) 0.025(2) 0.000(2) -0.003(2) -0.015(2) C2A 0.034(4) 0.027(4) 0.031(4) 0.006(3) -0.009(3) -0.008(3) C2B 0.033(9) 0.029(9) 0.035(9) 0.003(8) -0.001(7) 0.005(7) C4 0.059(4) 0.024(3) 0.046(3) -0.003(3) 0.003(3) 0.008(3) C6 0.036(3) 0.026(3) 0.033(3) -0.007(2) -0.014(2) 0.004(2) C7 0.040(3) 0.036(3) 0.030(3) 0.005(2) -0.013(2) -0.007(2) C8 0.035(3) 0.039(3) 0.033(3) 0.001(2) -0.008(2) -0.001(2) C9 0.034(3) 0.036(3) 0.039(3) 0.000(2) -0.012(2) -0.007(2) C10 0.032(3) 0.029(3) 0.026(2) 0.001(2) -0.002(2) -0.005(2) C11 0.038(3) 0.034(3) 0.028(2) 0.001(2) 0.000(2) 0.003(2) C12 0.042(3) 0.050(4) 0.042(3) -0.008(3) 0.000(3) 0.012(3) C13 0.041(3) 0.059(4) 0.041(3) -0.011(3) 0.015(3) -0.004(3) C14 0.060(4) 0.043(3) 0.032(3) -0.005(3) 0.007(3) -0.015(3) C15 0.045(3) 0.037(3) 0.029(3) 0.008(2) -0.002(2) -0.006(3) C16 0.032(3) 0.023(2) 0.030(2) 0.006(2) -0.009(2) -0.007(2) C17 0.047(3) 0.046(4) 0.036(3) -0.002(3) -0.010(3) -0.008(3) C18 0.067(4) 0.046(4) 0.029(3) 0.006(3) -0.016(3) -0.024(3) C19 0.047(4) 0.044(3) 0.053(4) 0.017(3) -0.030(3) -0.016(3) C20 0.036(3) 0.050(4) 0.062(4) 0.008(3) -0.020(3) -0.005(3) C21 0.035(3) 0.037(3) 0.040(3) 0.005(3) -0.007(2) -0.004(2) C22 0.030(3) 0.033(3) 0.025(2) 0.003(2) -0.006(2) -0.004(2) C23 0.051(4) 0.038(3) 0.034(3) 0.009(3) -0.009(3) -0.012(3) C25A 0.042(7) 0.038(7) 0.043(7) 0.015(6) -0.014(6) -0.001(6) C25B 0.062(9) 0.062(9) 0.042(7) 0.019(7) -0.003(6) -0.014(7) C26A 0.058(9) 0.043(8) 0.034(6) 0.010(6) 0.005(7) -0.010(8) C26B 0.036(7) 0.048(9) 0.039(7) 0.018(7) -0.008(6) -0.003(7) C27 0.021(2) 0.039(3) 0.022(2) 0.002(2) -0.0012(18) 0.001(2) C28 0.041(3) 0.042(3) 0.026(3) -0.015(2) 0.004(2) 0.003(3) C29 0.047(4) 0.086(6) 0.045(4) -0.032(4) 0.019(3) -0.012(4) C30 0.062(4) 0.081(5) 0.030(3) -0.007(3) 0.017(3) -0.030(4) C31 0.028(2) 0.026(3) 0.023(2) 0.000(2) -0.0038(19) -0.007(2) C32 0.030(3) 0.038(3) 0.028(3) -0.002(2) -0.003(2) 0.002(2) C33 0.040(3) 0.052(4) 0.037(3) -0.004(3) 0.002(2) 0.009(3) C34 0.050(3) 0.046(3) 0.024(3) -0.011(2) 0.002(2) 0.002(3) C35 0.040(3) 0.046(3) 0.027(3) -0.002(2) -0.007(2) -0.009(3) C36 0.032(3) 0.041(3) 0.025(2) -0.001(2) -0.004(2) -0.005(2) C37 0.023(2) 0.038(3) 0.024(2) 0.009(2) -0.0029(19) -0.002(2) C38 0.029(3) 0.042(3) 0.030(3) 0.003(2) 0.000(2) -0.004(2) C39 0.030(3) 0.056(4) 0.034(3) 0.014(3) -0.006(2) -0.015(3) C40 0.026(3) 0.061(4) 0.039(3) 0.019(3) 0.004(2) 0.008(3) C41 0.033(3) 0.047(4) 0.044(3) 0.004(3) 0.007(2) 0.007(3) C42 0.032(3) 0.032(3) 0.033(3) 0.007(2) 0.002(2) 0.004(2) Br1 0.0332(3) 0.0446(4) 0.0426(3) 0.0050(3) -0.0036(2) -0.0047(2) Br2 0.0729(5) 0.0499(4) 0.0553(4) 0.0047(3) -0.0123(3) 0.0015(3) O1 0.072(3) 0.066(3) 0.077(3) -0.001(3) 0.006(3) -0.010(3) O2 0.104(4) 0.088(4) 0.060(3) 0.004(3) -0.024(3) -0.035(4) O3 0.073(3) 0.057(3) 0.064(3) 0.008(3) -0.001(3) -0.003(3) O4 0.120(5) 0.081(4) 0.086(4) 0.017(3) -0.045(4) -0.028(4) O5 0.063(3) 0.040(2) 0.054(3) 0.005(2) -0.003(2) 0.003(2) O6 0.082(4) 0.075(4) 0.057(3) -0.018(3) 0.006(3) -0.016(3) C5 0.054(4) 0.025(3) 0.075(4) 0.001(3) -0.030(3) -0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 1.927(4) . ? Ni1 N1 1.936(4) . ? Ni1 P2 2.1217(14) . ? Ni1 P1 2.1263(14) . ? P1 C10 1.808(5) . ? P1 C16 1.811(5) . ? P1 C1B 1.854(17) . ? P1 C1A 1.879(7) . ? P2 C31 1.808(5) . ? P2 C37 1.811(5) . ? P2 C22 1.832(5) . ? N1 C6 1.301(6) . ? N1 C7 1.472(6) . ? N2 C6 1.335(7) . ? N2 C9 1.464(6) . ? N2 C5 1.478(7) . ? N3 C27 1.307(6) . ? N3 C28 1.472(6) . ? N4 C27 1.345(6) . ? N4 C26A 1.386(14) . ? N4 C30 1.456(8) . ? N4 C26B 1.643(15) . ? C1A C2A 1.492(10) . ? C1A C6 1.531(8) . ? C1A H1A 0.9800 . ? C1B C2B 1.54(2) . ? C1B C6 1.580(16) . ? C1B H1B 0.9800 . ? C2A C3A 1.572(13) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C2B C3B 1.47(3) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4 1.528(5) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4 C5 1.509(8) . ? C4 C3A 1.549(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C7 C8 1.505(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.532(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.381(7) . ? C10 C15 1.408(7) . ? C11 C12 1.386(8) . ? C11 H11 0.9300 . ? C12 C13 1.378(9) . ? C12 H12 0.9300 . ? C13 C14 1.392(9) . ? C13 H13 0.9300 . ? C14 C15 1.387(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.388(8) . ? C16 C17 1.393(8) . ? C17 C18 1.392(8) . ? C17 H17 0.9300 . ? C18 C19 1.371(9) . ? C18 H18 0.9300 . ? C19 C20 1.379(9) . ? C19 H19 0.9300 . ? C20 C21 1.378(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C27 1.513(7) . ? C22 C23 1.542(7) . ? C22 H22 0.9800 . ? C23 C24B 1.485(8) . ? C23 C24A 1.601(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24B C25B 1.519(3) . ? C24B H24A 0.9700 . ? C24B H24B 0.9700 . ? C25A C26A 1.516(18) . ? C25A C24A 1.522(3) . ? C25A H25A 0.9700 . ? C25A H25B 0.9700 . ? C25B C26B 1.503(9) . ? C25B H25C 0.9700 . ? C25B H25D 0.9700 . ? C24A H24C 0.9700 . ? C24A H24D 0.9700 . ? C26A H26A 0.9700 . ? C26A H26B 0.9700 . ? C26B H26C 0.9700 . ? C26B H26D 0.9700 . ? C28 C29 1.524(8) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.496(11) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.387(7) . ? C31 C36 1.394(6) . ? C32 C33 1.384(8) . ? C32 H32 0.9300 . ? C33 C34 1.392(8) . ? C33 H33 0.9300 . ? C34 C35 1.365(8) . ? C34 H34 0.9300 . ? C35 C36 1.389(7) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C42 1.396(7) . ? C37 C38 1.396(7) . ? C38 C39 1.400(8) . ? C38 H38 0.9300 . ? C39 C40 1.368(9) . ? C39 H39 0.9300 . ? C40 C41 1.369(9) . ? C40 H40 0.9300 . ? C41 C42 1.388(7) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C5 H5A1 0.9700 . ? C5 H5A2 0.9700 . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? 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 N3 Ni1 N1 97.92(17) . . ? N3 Ni1 P2 81.89(13) . . ? N1 Ni1 P2 173.84(13) . . ? N3 Ni1 P1 169.66(13) . . ? N1 Ni1 P1 80.92(13) . . ? P2 Ni1 P1 100.38(5) . . ? C10 P1 C16 109.0(2) . . ? C10 P1 C1B 93.4(6) . . ? C16 P1 C1B 107.8(5) . . ? C10 P1 C1A 109.5(3) . . ? C16 P1 C1A 106.1(3) . . ? C10 P1 Ni1 115.08(17) . . ? C16 P1 Ni1 122.01(17) . . ? C1B P1 Ni1 105.3(5) . . ? C1A P1 Ni1 93.0(2) . . ? C31 P2 C37 108.8(2) . . ? C31 P2 C22 106.4(2) . . ? C37 P2 C22 107.3(2) . . ? C31 P2 Ni1 120.76(16) . . ? C37 P2 Ni1 113.38(18) . . ? C22 P2 Ni1 98.78(16) . . ? C6 N1 C7 118.4(4) . . ? C6 N1 Ni1 122.0(3) . . ? C7 N1 Ni1 119.4(3) . . ? C6 N2 C9 120.3(4) . . ? C6 N2 C5 125.3(4) . . ? C9 N2 C5 113.6(4) . . ? C27 N3 C28 118.2(4) . . ? C27 N3 Ni1 122.8(3) . . ? C28 N3 Ni1 119.0(3) . . ? C27 N4 C26A 131.5(7) . . ? C27 N4 C30 120.9(5) . . ? C26A N4 C30 107.5(7) . . ? C27 N4 C26B 112.7(7) . . ? C30 N4 C26B 118.9(7) . . ? C2A C1A C6 116.7(6) . . ? C2A C1A P1 113.6(5) . . ? C6 C1A P1 99.8(4) . . ? C2A C1A H1A 108.7 . . ? C6 C1A H1A 108.7 . . ? P1 C1A H1A 108.7 . . ? C2B C1B C6 106.9(12) . . ? C2B C1B P1 113.8(12) . . ? C6 C1B P1 99.1(9) . . ? C2B C1B H1B 112.1 . . ? C6 C1B H1B 112.1 . . ? P1 C1B H1B 112.1 . . ? C1A C2A C3A 110.7(7) . . ? C1A C2A H2A1 109.5 . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? C3A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C3B C2B C1B 110.9(14) . . ? C3B C2B H2B1 109.5 . . ? C1B C2B H2B1 109.5 . . ? C3B C2B H2B2 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 108.0 . . ? C2B C3B C4 108.9(17) . . ? C2B C3B H3B1 109.9 . . ? C4 C3B H3B1 109.9 . . ? C2B C3B H3B2 109.9 . . ? C4 C3B H3B2 109.9 . . ? H3B1 C3B H3B2 108.3 . . ? C5 C4 C3B 119.2(8) . . ? C5 C4 C3A 112.4(5) . . ? C5 C4 H4A 109.1 . . ? C3B C4 H4A 97.8 . . ? C3A C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3B C4 H4B 112.7 . . ? C3A C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? N1 C6 N2 124.9(4) . . ? N1 C6 C1A 112.0(5) . . ? N2 C6 C1A 123.0(5) . . ? N1 C6 C1B 120.3(7) . . ? N2 C6 C1B 112.4(8) . . ? N1 C7 C8 110.6(4) . . ? N1 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 106.9(5) . . ? C7 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? C7 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? N2 C9 C8 109.8(4) . . ? N2 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C15 119.5(5) . . ? C11 C10 P1 118.6(4) . . ? C15 C10 P1 121.6(4) . . ? C10 C11 C12 120.3(5) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.2(6) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.4(5) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 120.0(5) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? C21 C16 C17 119.4(5) . . ? C21 C16 P1 118.9(4) . . ? C17 C16 P1 121.4(4) . . ? C18 C17 C16 119.3(6) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C19 C18 C17 120.2(6) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.9(5) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 119.2(6) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C16 120.9(6) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C27 C22 C23 116.0(4) . . ? C27 C22 P2 103.7(3) . . ? C23 C22 P2 113.4(3) . . ? C27 C22 H22 107.8 . . ? C23 C22 H22 107.8 . . ? P2 C22 H22 107.8 . . ? C24B C23 C22 122.0(8) . . ? C22 C23 C24A 111.0(5) . . ? C24B C23 H23A 106.8 . . ? C22 C23 H23A 106.8 . . ? C24A C23 H23A 104.8 . . ? C24B C23 H23B 106.8 . . ? C22 C23 H23B 106.8 . . ? C24A C23 H23B 119.9 . . ? H23A C23 H23B 106.7 . . ? C23 C24B C25B 114.4(9) . . ? C23 C24B H24A 108.7 . . ? C25B C24B H24A 108.7 . . ? C23 C24B H24B 108.7 . . ? C25B C24B H24B 108.7 . . ? H24A C24B H24B 107.6 . . ? C26A C25A C24A 116.5(11) . . ? C26A C25A H25A 108.2 . . ? C24A C25A H25A 108.2 . . ? C26A C25A H25B 108.2 . . ? C24A C25A H25B 108.2 . . ? H25A C25A H25B 107.3 . . ? C26B C25B C24B 108.6(12) . . ? C26B C25B H25C 110.0 . . ? C24B C25B H25C 110.0 . . ? C26B C25B H25D 110.0 . . ? C24B C25B H25D 110.0 . . ? H25C C25B H25D 108.3 . . ? C25A C24A C23 108.6(7) . . ? C25A C24A H24C 110.0 . . ? C23 C24A H24C 110.0 . . ? C25A C24A H24D 110.0 . . ? C23 C24A H24D 110.0 . . ? H24C C24A H24D 108.3 . . ? N4 C26A C25A 114.9(11) . . ? N4 C26A H26A 108.5 . . ? C25A C26A H26A 108.5 . . ? N4 C26A H26B 108.5 . . ? C25A C26A H26B 108.5 . . ? H26A C26A H26B 107.5 . . ? C25B C26B N4 111.0(10) . . ? C25B C26B H26C 109.4 . . ? N4 C26B H26C 109.4 . . ? C25B C26B H26D 109.4 . . ? N4 C26B H26D 109.4 . . ? H26C C26B H26D 108.0 . . ? N3 C27 N4 124.3(5) . . ? N3 C27 C22 115.2(4) . . ? N4 C27 C22 120.4(5) . . ? N3 C28 C29 109.4(5) . . ? N3 C28 H28A 109.8 . . ? C29 C28 H28A 109.8 . . ? N3 C28 H28B 109.8 . . ? C29 C28 H28B 109.8 . . ? H28A C28 H28B 108.2 . . ? C30 C29 C28 107.8(5) . . ? C30 C29 H29A 110.1 . . ? C28 C29 H29A 110.1 . . ? C30 C29 H29B 110.1 . . ? C28 C29 H29B 110.1 . . ? H29A C29 H29B 108.5 . . ? N4 C30 C29 110.1(5) . . ? N4 C30 H30A 109.6 . . ? C29 C30 H30A 109.6 . . ? N4 C30 H30B 109.6 . . ? C29 C30 H30B 109.6 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C36 119.2(5) . . ? C32 C31 P2 118.9(4) . . ? C36 C31 P2 121.8(4) . . ? C33 C32 C31 120.2(5) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 120.1(5) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 119.8(5) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 120.6(5) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C36 C31 120.0(5) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C42 C37 C38 118.3(5) . . ? C42 C37 P2 117.7(4) . . ? C38 C37 P2 124.0(4) . . ? C37 C38 C39 119.9(5) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C40 C39 C38 120.2(5) . . ? C40 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C39 C40 C41 120.9(5) . . ? C39 C40 H40 119.5 . . ? C41 C40 H40 119.5 . . ? C40 C41 C42 119.5(6) . . ? C40 C41 H41 120.2 . . ? C42 C41 H41 120.2 . . ? C41 C42 C37 121.1(5) . . ? C41 C42 H42 119.4 . . ? C37 C42 H42 119.4 . . ? N2 C5 C4 114.5(5) . . ? N2 C5 H5A1 108.6 . . ? C4 C5 H5A1 108.6 . . ? N2 C5 H5A2 108.6 . . ? C4 C5 H5A2 108.6 . . ? H5A1 C5 H5A2 107.6 . . ? C4 C3A C2A 109.9(7) . . ? C4 C3A H3A1 109.7 . . ? C2A C3A H3A1 109.7 . . ? C4 C3A H3A2 109.7 . . ? C2A C3A H3A2 109.7 . . ? H3A1 C3A H3A2 108.2 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.680 _refine_diff_density_min -2.091 _refine_diff_density_rms 0.111 # Attachment 'dbup.cif' data_DBUP _database_code_depnum_ccdc_archive 'CCDC 724933' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H25 N2 P' _chemical_formula_sum 'C21 H25 N2 P' _chemical_properties_physical air-sensitive _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colorless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 336.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1020 0.0940 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6126(5) _cell_length_b 15.5139(14) _cell_length_c 14.4029(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.505(4) _cell_angle_gamma 90.00 _cell_volume 1814.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6052 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.052 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6624 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.49 _reflns_number_total 3755 _reflns_number_gt 2218 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.1033P)^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 3755 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.35285(10) 0.76774(6) 0.39205(6) 0.0284(3) Uani 1 1 d . . . N1 N 0.0848(3) 0.65413(18) 0.32475(19) 0.0340(7) Uani 1 1 d . . . N2 N 0.0349(3) 0.64895(17) 0.15273(17) 0.0286(6) Uani 1 1 d . . . C1 C 0.2394(4) 0.74991(19) 0.2585(2) 0.0267(7) Uani 1 1 d . . . H1 H 0.3182 0.7314 0.2267 0.032 Uiso 1 1 calc R . . C2 C 0.1536(4) 0.8335(2) 0.2075(2) 0.0311(8) Uani 1 1 d . . . H2A H 0.0472 0.8380 0.2165 0.037 Uiso 1 1 calc R . . H2B H 0.2191 0.8826 0.2401 0.037 Uiso 1 1 calc R . . C3 C 0.1279(4) 0.8391(2) 0.0979(2) 0.0346(8) Uani 1 1 d . . . H3A H 0.0786 0.8945 0.0739 0.042 Uiso 1 1 calc R . . H3B H 0.2350 0.8375 0.0894 0.042 Uiso 1 1 calc R . . C4 C 0.0211(4) 0.7689(2) 0.0340(2) 0.0341(8) Uani 1 1 d . . . H4A H -0.0911 0.7763 0.0334 0.041 Uiso 1 1 calc R . . H4B H 0.0203 0.7762 -0.0331 0.041 Uiso 1 1 calc R . . C5 C 0.0764(4) 0.6780(2) 0.0672(2) 0.0309(8) Uani 1 1 d . . . H5A H 0.0266 0.6389 0.0129 0.037 Uiso 1 1 calc R . . H5B H 0.1949 0.6746 0.0830 0.037 Uiso 1 1 calc R . . C6 C 0.1123(3) 0.6792(2) 0.2464(2) 0.0267(7) Uani 1 1 d . . . C7 C -0.0446(4) 0.5897(2) 0.3100(2) 0.0420(9) Uani 1 1 d . . . H7A H -0.0843 0.5903 0.3656 0.050 Uiso 1 1 calc R . . H7B H -0.0006 0.5329 0.3059 0.050 Uiso 1 1 calc R . . C8 C -0.1863(4) 0.6089(2) 0.2158(2) 0.0416(9) Uani 1 1 d . . . H8A H -0.2735 0.5669 0.2072 0.050 Uiso 1 1 calc R . . H8B H -0.2307 0.6657 0.2198 0.050 Uiso 1 1 calc R . . C9 C -0.1249(4) 0.6050(2) 0.1291(2) 0.0363(8) Uani 1 1 d . . . H9A H -0.1134 0.5453 0.1124 0.044 Uiso 1 1 calc R . . H9B H -0.2044 0.6324 0.0724 0.044 Uiso 1 1 calc R . . C10 C 0.4801(4) 0.6708(2) 0.4288(2) 0.0278(7) Uani 1 1 d . . . C11 C 0.4958(4) 0.6059(2) 0.3654(2) 0.0310(8) Uani 1 1 d . . . H11 H 0.4344 0.6091 0.2987 0.037 Uiso 1 1 calc R . . C12 C 0.6013(4) 0.5365(2) 0.3999(2) 0.0354(8) Uani 1 1 d . . . H12 H 0.6094 0.4940 0.3562 0.042 Uiso 1 1 calc R . . C13 C 0.6936(4) 0.5302(2) 0.4977(2) 0.0366(8) Uani 1 1 d . . . H13 H 0.7646 0.4839 0.5204 0.044 Uiso 1 1 calc R . . C14 C 0.6800(4) 0.5932(2) 0.5619(2) 0.0394(9) Uani 1 1 d . . . H14 H 0.7422 0.5892 0.6284 0.047 Uiso 1 1 calc R . . C15 C 0.5740(4) 0.6628(2) 0.5281(2) 0.0341(8) Uani 1 1 d . . . H15 H 0.5657 0.7046 0.5725 0.041 Uiso 1 1 calc R . . C16 C 0.5127(4) 0.8409(2) 0.3768(2) 0.0276(7) Uani 1 1 d . . . C17 C 0.5040(4) 0.9281(2) 0.3979(2) 0.0331(8) Uani 1 1 d . . . H17 H 0.4210 0.9472 0.4207 0.040 Uiso 1 1 calc R . . C18 C 0.6162(4) 0.9866(2) 0.3855(2) 0.0400(9) Uani 1 1 d . . . H18 H 0.6073 1.0447 0.3989 0.048 Uiso 1 1 calc R . . C19 C 0.7416(4) 0.9590(2) 0.3531(2) 0.0435(9) Uani 1 1 d . . . H19 H 0.8164 0.9985 0.3439 0.052 Uiso 1 1 calc R . . C20 C 0.7557(4) 0.8729(2) 0.3343(2) 0.0386(9) Uani 1 1 d . . . H20 H 0.8417 0.8542 0.3139 0.046 Uiso 1 1 calc R . . C21 C 0.6425(4) 0.8139(2) 0.3456(2) 0.0331(8) Uani 1 1 d . . . H21 H 0.6528 0.7559 0.3324 0.040 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 P1 0.0278(4) 0.0283(5) 0.0299(5) -0.0028(4) 0.0107(4) -0.0044(4) N1 0.0312(15) 0.0417(18) 0.0302(15) -0.0030(13) 0.0115(13) -0.0128(13) N2 0.0280(14) 0.0308(16) 0.0257(14) -0.0021(12) 0.0074(11) -0.0044(12) C1 0.0235(15) 0.0255(18) 0.0325(17) 0.0008(14) 0.0112(14) -0.0010(13) C2 0.0267(16) 0.0272(19) 0.0368(18) 0.0017(15) 0.0069(14) 0.0010(13) C3 0.0322(17) 0.032(2) 0.041(2) 0.0107(16) 0.0143(16) 0.0061(15) C4 0.0365(18) 0.037(2) 0.0293(17) 0.0041(15) 0.0121(15) 0.0038(16) C5 0.0326(17) 0.035(2) 0.0255(16) 0.0003(15) 0.0098(14) 0.0039(15) C6 0.0209(15) 0.0253(18) 0.0333(18) -0.0034(14) 0.0080(14) -0.0006(13) C7 0.041(2) 0.045(2) 0.040(2) -0.0031(18) 0.0138(17) -0.0181(18) C8 0.0291(18) 0.046(2) 0.051(2) -0.0085(18) 0.0146(17) -0.0118(16) C9 0.0287(17) 0.040(2) 0.0361(19) -0.0035(16) 0.0053(15) -0.0067(15) C10 0.0264(16) 0.0290(19) 0.0284(17) -0.0003(14) 0.0096(14) -0.0089(14) C11 0.0321(17) 0.030(2) 0.0286(17) 0.0030(15) 0.0063(15) -0.0013(14) C12 0.0394(19) 0.031(2) 0.0391(19) 0.0012(16) 0.0175(17) -0.0029(16) C13 0.0300(18) 0.038(2) 0.040(2) 0.0089(17) 0.0091(16) 0.0005(16) C14 0.0349(19) 0.044(2) 0.0326(19) 0.0084(17) 0.0021(16) -0.0067(17) C15 0.0363(18) 0.037(2) 0.0287(17) -0.0050(16) 0.0100(15) -0.0095(16) C16 0.0260(16) 0.0281(19) 0.0257(16) -0.0024(14) 0.0046(14) -0.0033(13) C17 0.0327(17) 0.0272(19) 0.0355(18) -0.0008(15) 0.0063(15) -0.0007(15) C18 0.041(2) 0.027(2) 0.041(2) 0.0049(16) 0.0006(17) -0.0093(16) C19 0.037(2) 0.043(2) 0.042(2) 0.0129(18) 0.0030(17) -0.0144(17) C20 0.0317(18) 0.048(2) 0.0367(19) 0.0057(17) 0.0114(16) -0.0044(16) C21 0.0336(17) 0.030(2) 0.0355(19) 0.0006(15) 0.0116(15) -0.0051(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 P1 C10 1.832(3) . ? P1 C16 1.853(3) . ? P1 C1 1.865(3) . ? N1 C6 1.288(4) . ? N1 C7 1.459(4) . ? N2 C6 1.372(4) . ? N2 C5 1.464(4) . ? N2 C9 1.470(4) . ? C1 C6 1.518(4) . ? C1 C2 1.551(4) . ? C1 H1 0.9800 . ? C2 C3 1.522(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.514(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.521(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.511(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.395(4) . ? C10 C11 1.395(4) . ? C11 C12 1.389(4) . ? C11 H11 0.9300 . ? C12 C13 1.370(4) . ? C12 H12 0.9300 . ? C13 C14 1.377(5) . ? C13 H13 0.9300 . ? C14 C15 1.393(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.394(4) . ? C16 C21 1.400(4) . ? C17 C18 1.380(4) . ? C17 H17 0.9300 . ? C18 C19 1.380(5) . ? C18 H18 0.9300 . ? C19 C20 1.376(5) . ? C19 H19 0.9300 . ? C20 C21 1.386(4) . ? C20 H20 0.9300 . ? C21 H21 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 C10 P1 C16 98.08(13) . . ? C10 P1 C1 103.46(14) . . ? C16 P1 C1 97.05(13) . . ? C6 N1 C7 115.7(3) . . ? C6 N2 C5 123.1(3) . . ? C6 N2 C9 119.8(2) . . ? C5 N2 C9 114.9(2) . . ? C6 C1 C2 109.8(2) . . ? C6 C1 P1 109.6(2) . . ? C2 C1 P1 111.5(2) . . ? C6 C1 H1 108.6 . . ? C2 C1 H1 108.6 . . ? P1 C1 H1 108.6 . . ? C3 C2 C1 114.8(3) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C4 C3 C2 115.9(3) . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C5 C4 C3 114.3(3) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? N2 C5 C4 114.4(2) . . ? N2 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? N2 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N1 C6 N2 125.9(3) . . ? N1 C6 C1 117.0(3) . . ? N2 C6 C1 117.1(3) . . ? N1 C7 C8 110.0(3) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C7 109.4(3) . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N2 C9 C8 110.4(3) . . ? N2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C15 C10 C11 117.2(3) . . ? C15 C10 P1 117.1(2) . . ? C11 C10 P1 125.6(2) . . ? C12 C11 C10 121.3(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.3(3) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C17 C16 C21 117.8(3) . . ? C17 C16 P1 118.2(2) . . ? C21 C16 P1 124.0(2) . . ? C18 C17 C16 121.3(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.4(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C16 120.5(3) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.101