# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name M.Babashkina _publ_contact_author_name 'Dr. Michael Bolte' _publ_contact_author_email bolte@chemie.uni-frankfurt.de #============================================================================== data_safin30 _database_code_depnum_ccdc_archive 'CCDC 721784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H25 N2 O2 P S2' _chemical_formula_sum 'C15 H25 N2 O2 P S2' _chemical_formula_weight 360.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1225(6) _cell_length_b 10.4047(7) _cell_length_c 10.5936(7) _cell_angle_alpha 114.921(5) _cell_angle_beta 92.754(5) _cell_angle_gamma 107.180(5) _cell_volume 947.35(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10742 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 25.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8775 _exptl_absorpt_correction_T_max 0.8868 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13936 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 25.55 _reflns_number_total 3538 _reflns_number_gt 3341 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0345P)^2^+0.3604P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3538 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.25959(3) 0.69803(4) 0.17608(3) 0.01895(11) Uani 1 1 d . . . S1 S 0.44743(3) 0.87311(4) 0.61449(3) 0.02447(11) Uani 1 1 d . . . S2 S 0.19646(4) 0.48159(4) 0.09494(3) 0.02762(11) Uani 1 1 d . . . O1 O 0.13339(10) 0.75480(11) 0.17189(10) 0.0256(2) Uani 1 1 d . . . O2 O 0.36554(9) 0.77706(10) 0.10519(9) 0.0221(2) Uani 1 1 d . . . N1 N 0.34809(12) 0.79089(13) 0.34569(11) 0.0216(2) Uani 1 1 d . . . H1 H 0.4131(19) 0.878(2) 0.3660(19) 0.035(5) Uiso 1 1 d . . . N2 N 0.23333(12) 0.63009(13) 0.43541(12) 0.0210(2) Uani 1 1 d . . . H2 H 0.1916(19) 0.571(2) 0.350(2) 0.034(5) Uiso 1 1 d . . . C1 C 0.33578(13) 0.75670(14) 0.45754(13) 0.0187(3) Uani 1 1 d . . . C2 C 0.47508(15) 0.71987(17) 0.03861(15) 0.0288(3) Uani 1 1 d . . . H2A H 0.4306 0.6097 -0.0288 0.035 Uiso 1 1 calc R . . C3 C 0.58848(18) 0.7411(2) 0.15001(19) 0.0443(4) Uani 1 1 d . . . H3A H 0.5479 0.6807 0.1981 0.067 Uiso 1 1 calc R . . H3B H 0.6285 0.8482 0.2195 0.067 Uiso 1 1 calc R . . H3C H 0.6629 0.7084 0.1050 0.067 Uiso 1 1 calc R . . C4 C 0.5274(2) 0.8059(2) -0.0441(2) 0.0504(5) Uani 1 1 d . . . H4A H 0.4488 0.7862 -0.1153 0.076 Uiso 1 1 calc R . . H4B H 0.6006 0.7730 -0.0917 0.076 Uiso 1 1 calc R . . H4C H 0.5669 0.9144 0.0209 0.076 Uiso 1 1 calc R . . C5 C 0.15264(15) 0.91627(16) 0.22554(16) 0.0290(3) Uani 1 1 d . . . H5 H 0.2551 0.9782 0.2640 0.035 Uiso 1 1 calc R . . C6 C 0.0721(3) 0.9555(2) 0.3435(3) 0.0661(6) Uani 1 1 d . . . H6A H 0.1098 0.9375 0.4191 0.099 Uiso 1 1 calc R . . H6B H -0.0278 0.8922 0.3066 0.099 Uiso 1 1 calc R . . H6C H 0.0817 1.0622 0.3817 0.099 Uiso 1 1 calc R . . C7 C 0.1024(3) 0.9365(2) 0.1021(2) 0.0619(6) Uani 1 1 d . . . H7A H 0.1581 0.9063 0.0289 0.093 Uiso 1 1 calc R . . H7B H 0.1134 1.0430 0.1340 0.093 Uiso 1 1 calc R . . H7C H 0.0027 0.8737 0.0626 0.093 Uiso 1 1 calc R . . C11 C 0.21894(13) 0.56820(14) 0.53456(13) 0.0207(3) Uani 1 1 d . . . C12 C 0.26851(14) 0.45003(16) 0.50967(15) 0.0259(3) Uani 1 1 d . . . C13 C 0.25207(17) 0.38743(18) 0.60387(17) 0.0361(4) Uani 1 1 d . . . H13 H 0.2861 0.3076 0.5901 0.043 Uiso 1 1 calc R . . C14 C 0.18693(18) 0.44020(19) 0.71666(17) 0.0400(4) Uani 1 1 d . . . H14 H 0.1762 0.3962 0.7797 0.048 Uiso 1 1 calc R . . C15 C 0.13728(16) 0.55650(19) 0.73850(15) 0.0356(4) Uani 1 1 d . . . H15 H 0.0925 0.5916 0.8166 0.043 Uiso 1 1 calc R . . C16 C 0.15179(14) 0.62348(16) 0.64751(14) 0.0259(3) Uani 1 1 d . . . C17 C 0.33547(17) 0.38980(19) 0.38357(17) 0.0361(3) Uani 1 1 d . . . H17A H 0.3756 0.3176 0.3907 0.054 Uiso 1 1 calc R . . H17B H 0.4105 0.4737 0.3820 0.054 Uiso 1 1 calc R . . H17C H 0.2639 0.3390 0.2960 0.054 Uiso 1 1 calc R . . C18 C 0.09699(16) 0.74876(19) 0.67047(17) 0.0363(4) Uani 1 1 d . . . H18A H 0.0332 0.7539 0.7378 0.054 Uiso 1 1 calc R . . H18B H 0.0457 0.7295 0.5798 0.054 Uiso 1 1 calc R . . H18C H 0.1762 0.8449 0.7089 0.054 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 0.02141(18) 0.01845(17) 0.01440(17) 0.00685(13) 0.00314(12) 0.00448(13) S1 0.02596(18) 0.02197(18) 0.01853(17) 0.01021(14) -0.00309(13) -0.00130(13) S2 0.0374(2) 0.01873(18) 0.01880(17) 0.00530(13) 0.00530(14) 0.00408(14) O1 0.0216(5) 0.0227(5) 0.0264(5) 0.0074(4) 0.0022(4) 0.0057(4) O2 0.0249(5) 0.0246(5) 0.0203(4) 0.0125(4) 0.0083(4) 0.0093(4) N1 0.0246(6) 0.0180(6) 0.0168(5) 0.0082(4) 0.0013(4) 0.0003(5) N2 0.0229(5) 0.0195(6) 0.0149(5) 0.0077(5) 0.0004(4) 0.0006(4) C1 0.0200(6) 0.0187(6) 0.0176(6) 0.0080(5) 0.0045(5) 0.0074(5) C2 0.0323(7) 0.0292(7) 0.0259(7) 0.0105(6) 0.0153(6) 0.0137(6) C3 0.0370(9) 0.0558(11) 0.0455(9) 0.0182(8) 0.0126(7) 0.0299(8) C4 0.0538(11) 0.0627(12) 0.0524(11) 0.0374(10) 0.0348(9) 0.0234(9) C5 0.0261(7) 0.0227(7) 0.0331(8) 0.0087(6) 0.0024(6) 0.0083(6) C6 0.0883(16) 0.0452(11) 0.0704(14) 0.0186(11) 0.0470(13) 0.0377(11) C7 0.0866(16) 0.0423(11) 0.0557(12) 0.0242(10) -0.0109(11) 0.0221(11) C11 0.0184(6) 0.0207(6) 0.0180(6) 0.0098(5) -0.0002(5) -0.0007(5) C12 0.0239(7) 0.0232(7) 0.0249(7) 0.0107(6) -0.0022(5) 0.0020(5) C13 0.0406(8) 0.0284(8) 0.0359(8) 0.0193(7) -0.0063(7) 0.0029(6) C14 0.0428(9) 0.0401(9) 0.0304(8) 0.0250(7) -0.0049(7) -0.0062(7) C15 0.0275(7) 0.0466(9) 0.0214(7) 0.0163(7) 0.0039(6) -0.0036(7) C16 0.0187(6) 0.0296(7) 0.0201(6) 0.0089(6) 0.0012(5) -0.0001(5) C17 0.0401(8) 0.0341(8) 0.0350(8) 0.0121(7) 0.0070(7) 0.0195(7) C18 0.0289(8) 0.0404(9) 0.0322(8) 0.0089(7) 0.0097(6) 0.0131(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5637(10) . ? P1 O2 1.5707(9) . ? P1 N1 1.6839(11) . ? P1 S2 1.9195(5) . ? S1 C1 1.6800(13) . ? O1 C5 1.4747(17) . ? O2 C2 1.4807(16) . ? N1 C1 1.3745(16) . ? N1 H1 0.876(19) . ? N2 C1 1.3323(17) . ? N2 C11 1.4382(16) . ? N2 H2 0.849(19) . ? C2 C3 1.503(2) . ? C2 C4 1.509(2) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.499(2) . ? C5 C6 1.503(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C12 1.392(2) . ? C11 C16 1.3977(19) . ? C12 C13 1.396(2) . ? C12 C17 1.506(2) . ? C13 C14 1.379(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 C16 1.398(2) . ? C15 H15 0.9500 . ? C16 C18 1.496(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 103.41(5) . . ? O1 P1 N1 106.82(6) . . ? O2 P1 N1 100.79(5) . . ? O1 P1 S2 111.42(4) . . ? O2 P1 S2 118.02(4) . . ? N1 P1 S2 115.03(4) . . ? C5 O1 P1 122.62(8) . . ? C2 O2 P1 123.43(8) . . ? C1 N1 P1 132.05(9) . . ? C1 N1 H1 114.6(12) . . ? P1 N1 H1 113.3(12) . . ? C1 N2 C11 123.92(11) . . ? C1 N2 H2 116.1(12) . . ? C11 N2 H2 117.1(12) . . ? N2 C1 N1 117.40(11) . . ? N2 C1 S1 122.68(10) . . ? N1 C1 S1 119.92(10) . . ? O2 C2 C3 110.40(11) . . ? O2 C2 C4 105.15(12) . . ? C3 C2 C4 113.70(15) . . ? O2 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C4 C2 H2A 109.2 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C5 C7 107.20(13) . . ? O1 C5 C6 106.95(13) . . ? C7 C5 C6 114.34(18) . . ? O1 C5 H5 109.4 . . ? C7 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C16 122.65(12) . . ? C12 C11 N2 117.68(12) . . ? C16 C11 N2 119.62(12) . . ? C11 C12 C13 117.90(14) . . ? C11 C12 C17 121.04(12) . . ? C13 C12 C17 121.05(14) . . ? C14 C13 C12 120.72(15) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.40(14) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 121.07(14) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C11 C16 C15 117.25(14) . . ? C11 C16 C18 121.65(13) . . ? C15 C16 C18 121.10(14) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C5 -51.32(11) . . . . ? N1 P1 O1 C5 54.53(11) . . . . ? S2 P1 O1 C5 -179.07(9) . . . . ? O1 P1 O2 C2 -157.41(10) . . . . ? N1 P1 O2 C2 92.20(10) . . . . ? S2 P1 O2 C2 -33.90(11) . . . . ? O1 P1 N1 C1 91.07(13) . . . . ? O2 P1 N1 C1 -161.22(12) . . . . ? S2 P1 N1 C1 -33.14(14) . . . . ? C11 N2 C1 N1 171.05(12) . . . . ? C11 N2 C1 S1 -9.08(18) . . . . ? P1 N1 C1 N2 -2.65(19) . . . . ? P1 N1 C1 S1 177.48(8) . . . . ? P1 O2 C2 C3 -69.93(15) . . . . ? P1 O2 C2 C4 167.05(11) . . . . ? P1 O1 C5 C7 117.66(14) . . . . ? P1 O1 C5 C6 -119.29(15) . . . . ? C1 N2 C11 C12 -99.45(15) . . . . ? C1 N2 C11 C16 83.06(16) . . . . ? C16 C11 C12 C13 -1.26(19) . . . . ? N2 C11 C12 C13 -178.66(12) . . . . ? C16 C11 C12 C17 177.69(13) . . . . ? N2 C11 C12 C17 0.29(18) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C17 C12 C13 C14 -178.07(14) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 -0.1(2) . . . . ? C12 C11 C16 C15 0.96(19) . . . . ? N2 C11 C16 C15 178.31(12) . . . . ? C12 C11 C16 C18 -178.84(13) . . . . ? N2 C11 C16 C18 -1.48(19) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? C14 C15 C16 C18 179.52(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.876(19) 2.473(19) 3.3291(12) 165.9(16) 2_676 N2 H2 S2 0.849(19) 2.466(19) 3.2202(12) 148.5(16) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.254 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.041 data_safin32 _database_code_depnum_ccdc_archive 'CCDC 721785' # start Validation Reply Form _vrf_PLAT220_safin32 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.79 Ratio RESPONSE: This is an atom of a disordered isopropyl group. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H48 N4 Ni O4 P2 S4' _chemical_formula_sum 'C30 H48 N4 Ni O4 P2 S4' _chemical_formula_weight 777.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3417(10) _cell_length_b 10.4409(10) _cell_length_c 10.6637(10) _cell_angle_alpha 116.961(7) _cell_angle_beta 92.299(8) _cell_angle_gamma 106.498(8) _cell_volume 964.63(19) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9086 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 25.8 _exptl_crystal_description block _exptl_crystal_colour 'dark violet' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 410 _exptl_absorpt_coefficient_mu 0.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7519 _exptl_absorpt_correction_T_max 0.8239 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9493 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.63 _reflns_number_total 3597 _reflns_number_gt 2805 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0538P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.025(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3597 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.5000 0.0000 0.5000 0.02753(16) Uani 1 2 d S . . P1 P 0.72243(8) 0.25804(10) 0.79315(7) 0.0391(2) Uani 1 1 d . . . N1 N 0.6397(2) 0.1897(2) 0.62937(19) 0.0307(5) Uani 1 1 d . A . C1 C 0.6665(3) 0.2465(3) 0.5390(2) 0.0264(5) Uani 1 1 d . . . S1 S 0.55304(7) 0.12509(7) 0.37713(6) 0.03177(18) Uani 1 1 d . A . N2 N 0.7656(2) 0.3729(2) 0.5658(2) 0.0296(5) Uani 1 1 d . A . H2 H 0.809(3) 0.422(4) 0.647(3) 0.053(10) Uiso 1 1 d . . . C11 C 0.7788(3) 0.4366(2) 0.4709(2) 0.0259(5) Uani 1 1 d . . . C12 C 0.8452(3) 0.3821(3) 0.3568(2) 0.0318(6) Uani 1 1 d . A . C13 C 0.8561(3) 0.4487(3) 0.2680(3) 0.0448(8) Uani 1 1 d . . . H13 H 0.9001 0.4136 0.1885 0.054 Uiso 1 1 calc R A . C14 C 0.8044(3) 0.5637(3) 0.2936(3) 0.0508(9) Uani 1 1 d . A . H14 H 0.8125 0.6070 0.2316 0.061 Uiso 1 1 calc R . . C15 C 0.7410(3) 0.6166(3) 0.4080(3) 0.0453(7) Uani 1 1 d . . . H15 H 0.7060 0.6966 0.4249 0.054 Uiso 1 1 calc R A . C16 C 0.7275(3) 0.5540(3) 0.4997(2) 0.0321(6) Uani 1 1 d . A . C17 C 0.9030(3) 0.2573(3) 0.3307(3) 0.0459(7) Uani 1 1 d . . . H17A H 0.9547 0.2795 0.4214 0.069 Uiso 1 1 calc R A . H17B H 0.9645 0.2517 0.2622 0.069 Uiso 1 1 calc R . . H17C H 0.8276 0.1595 0.2914 0.069 Uiso 1 1 calc R . . C18 C 0.6606(3) 0.6122(3) 0.6274(3) 0.0480(8) Uani 1 1 d . . . H18A H 0.5856 0.5270 0.6228 0.072 Uiso 1 1 calc R A . H18B H 0.6236 0.6886 0.6267 0.072 Uiso 1 1 calc R . . H18C H 0.7289 0.6589 0.7159 0.072 Uiso 1 1 calc R . . O1 O 0.6164(2) 0.19493(19) 0.86861(16) 0.0337(4) Uani 1 1 d . A . C2 C 0.5289(3) 0.2762(3) 0.9532(3) 0.0392(7) Uani 1 1 d . . . H2A H 0.5868 0.3841 1.0223 0.047 Uiso 1 1 calc R A . C3 C 0.4209(4) 0.2755(4) 0.8547(4) 0.0602(9) Uani 1 1 d . A . H3A H 0.4649 0.3320 0.8066 0.090 Uiso 1 1 calc R . . H3B H 0.3590 0.3241 0.9104 0.090 Uiso 1 1 calc R . . H3C H 0.3680 0.1699 0.7827 0.090 Uiso 1 1 calc R . . C4 C 0.4750(5) 0.1944(4) 1.0349(4) 0.0772(13) Uani 1 1 d . A . H4A H 0.5522 0.2007 1.0963 0.116 Uiso 1 1 calc R . . H4B H 0.4228 0.0870 0.9674 0.116 Uiso 1 1 calc R . . H4C H 0.4148 0.2421 1.0945 0.116 Uiso 1 1 calc R . . S2 S 0.8249(2) 0.4589(3) 0.89394(16) 0.0314(5) Uani 0.643(7) 1 d P A 1 O2 O 0.8007(4) 0.1312(4) 0.7496(4) 0.0435(11) Uani 0.643(7) 1 d P A 1 C5 C 0.9146(7) 0.1473(7) 0.8376(9) 0.073(2) Uani 0.643(7) 1 d P A 1 H5 H 0.9655 0.2579 0.9050 0.087 Uiso 0.643(7) 1 calc PR A 1 C6 C 0.8563(9) 0.0664(8) 0.9217(8) 0.075(2) Uani 0.643(7) 1 d P A 1 H6A H 0.7996 0.1187 0.9831 0.112 Uiso 0.643(7) 1 calc PR A 1 H6B H 0.9320 0.0680 0.9813 0.112 Uiso 0.643(7) 1 calc PR A 1 H6C H 0.7997 -0.0397 0.8546 0.112 Uiso 0.643(7) 1 calc PR A 1 C7 C 1.0047(8) 0.0780(8) 0.7463(14) 0.125(5) Uani 0.643(7) 1 d P A 1 H7A H 1.0400 0.1345 0.6953 0.188 Uiso 0.643(7) 1 calc PR A 1 H7B H 0.9524 -0.0286 0.6765 0.188 Uiso 0.643(7) 1 calc PR A 1 H7C H 1.0818 0.0821 0.8061 0.188 Uiso 0.643(7) 1 calc PR A 1 S2' S 0.7961(4) 0.5115(6) 0.9038(3) 0.0332(9) Uani 0.357(7) 1 d P A 2 O2' O 0.8607(6) 0.2383(8) 0.8143(6) 0.038(2) Uani 0.357(7) 1 d P A 2 C5' C 0.8458(14) 0.0821(13) 0.7575(11) 0.046(3) Uani 0.357(7) 1 d P A 2 H5' H 0.7476 0.0133 0.7274 0.055 Uiso 0.357(7) 1 calc PR A 2 C6' C 0.933(3) 0.067(3) 0.8706(16) 0.147(11) Uani 0.357(7) 1 d P A 2 H6'1 H 0.8885 0.0853 0.9538 0.221 Uiso 0.357(7) 1 calc PR A 2 H6'2 H 1.0254 0.1423 0.9013 0.221 Uiso 0.357(7) 1 calc PR A 2 H6'3 H 0.9381 -0.0360 0.8274 0.221 Uiso 0.357(7) 1 calc PR A 2 C7' C 0.9245(14) 0.0477(12) 0.6335(11) 0.069(3) Uani 0.357(7) 1 d P A 2 H7'1 H 0.8792 0.0591 0.5584 0.103 Uiso 0.357(7) 1 calc PR A 2 H7'2 H 0.9251 -0.0571 0.5936 0.103 Uiso 0.357(7) 1 calc PR A 2 H7'3 H 1.0193 0.1193 0.6692 0.103 Uiso 0.357(7) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0400(3) 0.0235(2) 0.0242(2) 0.01571(18) 0.01153(18) 0.0102(2) P1 0.0339(4) 0.0667(5) 0.0329(3) 0.0337(3) 0.0120(3) 0.0223(4) N1 0.0449(14) 0.0300(10) 0.0220(9) 0.0167(8) 0.0090(9) 0.0120(10) C1 0.0346(15) 0.0228(11) 0.0262(11) 0.0134(9) 0.0108(10) 0.0123(10) S1 0.0434(4) 0.0265(3) 0.0245(3) 0.0160(2) 0.0052(3) 0.0045(3) N2 0.0353(13) 0.0281(10) 0.0246(10) 0.0153(9) 0.0045(9) 0.0057(9) C11 0.0278(14) 0.0234(11) 0.0240(11) 0.0137(9) 0.0026(9) 0.0017(10) C12 0.0296(14) 0.0333(13) 0.0289(12) 0.0151(10) 0.0059(10) 0.0057(11) C13 0.0436(18) 0.0527(17) 0.0297(13) 0.0222(12) 0.0098(12) 0.0005(14) C14 0.061(2) 0.0471(17) 0.0429(15) 0.0345(14) -0.0031(14) -0.0031(15) C15 0.053(2) 0.0324(14) 0.0499(16) 0.0248(13) -0.0075(14) 0.0083(13) C16 0.0331(15) 0.0267(12) 0.0309(12) 0.0125(10) -0.0010(10) 0.0061(11) C17 0.0419(18) 0.0474(16) 0.0455(15) 0.0168(13) 0.0172(13) 0.0200(14) C18 0.055(2) 0.0469(16) 0.0407(15) 0.0143(13) 0.0087(14) 0.0274(15) O1 0.0447(12) 0.0391(10) 0.0284(8) 0.0219(8) 0.0144(8) 0.0189(9) C2 0.0432(17) 0.0304(13) 0.0366(13) 0.0100(11) 0.0191(12) 0.0115(12) C3 0.048(2) 0.059(2) 0.073(2) 0.0239(17) 0.0160(17) 0.0300(17) C4 0.103(3) 0.071(2) 0.058(2) 0.0353(18) 0.052(2) 0.020(2) S2 0.0402(9) 0.0196(9) 0.0238(5) 0.0085(6) 0.0030(5) -0.0002(6) O2 0.031(2) 0.027(2) 0.065(2) 0.0145(19) -0.0019(17) 0.0128(18) C5 0.044(4) 0.033(3) 0.105(5) 0.008(3) -0.031(4) 0.013(3) C6 0.118(7) 0.065(4) 0.059(4) 0.036(3) -0.006(4) 0.051(4) C7 0.062(5) 0.071(5) 0.265(15) 0.086(7) 0.068(7) 0.040(4) S2' 0.0434(16) 0.0242(16) 0.0223(9) 0.0082(10) 0.0047(9) 0.0034(12) O2' 0.034(4) 0.042(4) 0.043(3) 0.023(3) 0.007(3) 0.017(3) C5' 0.045(7) 0.038(6) 0.058(6) 0.021(5) 0.004(5) 0.024(5) C6' 0.27(3) 0.176(19) 0.069(10) 0.057(11) 0.049(13) 0.17(2) C7' 0.072(8) 0.063(6) 0.062(6) 0.011(5) 0.019(6) 0.042(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.911(2) 2_656 ? Ni1 N1 1.911(2) . ? Ni1 S1 2.2195(6) . ? Ni1 S1 2.2195(6) 2_656 ? P1 O2' 1.524(6) . ? P1 O1 1.5575(18) . ? P1 N1 1.642(2) . ? P1 O2 1.645(4) . ? P1 S2 1.811(2) . ? P1 S2' 2.220(5) . ? N1 C1 1.343(3) . ? C1 N2 1.319(3) . ? C1 S1 1.724(2) . ? N2 C11 1.434(3) . ? N2 H2 0.80(3) . ? C11 C16 1.385(4) . ? C11 C12 1.392(3) . ? C12 C13 1.398(4) . ? C12 C17 1.503(4) . ? C13 C14 1.372(5) . ? C13 H13 0.9500 . ? C14 C15 1.372(4) . ? C14 H14 0.9500 . ? C15 C16 1.394(4) . ? C15 H15 0.9500 . ? C16 C18 1.506(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O1 C2 1.469(3) . ? C2 C4 1.497(4) . ? C2 C3 1.499(5) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? O2 C5 1.397(8) . ? C5 C7 1.469(10) . ? C5 C6 1.523(11) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O2' C5' 1.416(13) . ? C5' C7' 1.537(14) . ? C5' C6' 1.56(2) . ? C5' H5' 1.0000 . ? C6' H6'1 0.9800 . ? C6' H6'2 0.9800 . ? C6' H6'3 0.9800 . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 180.000(2) 2_656 . ? N1 Ni1 S1 105.49(6) 2_656 . ? N1 Ni1 S1 74.51(6) . . ? N1 Ni1 S1 74.51(6) 2_656 2_656 ? N1 Ni1 S1 105.49(6) . 2_656 ? S1 Ni1 S1 180.0 . 2_656 ? O2' P1 O1 113.4(2) . . ? O2' P1 N1 119.0(2) . . ? O1 P1 N1 105.65(11) . . ? O1 P1 O2 97.89(15) . . ? N1 P1 O2 95.38(16) . . ? O2' P1 S2 82.7(2) . . ? O1 P1 S2 116.52(9) . . ? N1 P1 S2 118.90(11) . . ? O2 P1 S2 118.70(15) . . ? O2' P1 S2' 97.7(3) . . ? O1 P1 S2' 111.19(11) . . ? N1 P1 S2' 109.76(13) . . ? O2 P1 S2' 133.55(17) . . ? C1 N1 P1 128.34(18) . . ? C1 N1 Ni1 98.54(14) . . ? P1 N1 Ni1 132.56(12) . . ? N2 C1 N1 126.4(2) . . ? N2 C1 S1 124.22(18) . . ? N1 C1 S1 109.39(17) . . ? C1 S1 Ni1 77.31(8) . . ? C1 N2 C11 123.5(2) . . ? C1 N2 H2 115(2) . . ? C11 N2 H2 121(2) . . ? C16 C11 C12 122.6(2) . . ? C16 C11 N2 117.9(2) . . ? C12 C11 N2 119.4(2) . . ? C11 C12 C13 117.2(3) . . ? C11 C12 C17 121.3(2) . . ? C13 C12 C17 121.5(2) . . ? C14 C13 C12 121.1(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 118.0(2) . . ? C11 C16 C18 120.6(2) . . ? C15 C16 C18 121.5(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 O1 P1 124.11(16) . . ? O1 C2 C4 104.4(2) . . ? O1 C2 C3 109.5(2) . . ? C4 C2 C3 114.9(3) . . ? O1 C2 H2A 109.3 . . ? C4 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O2 P1 124.2(4) . . ? O2 C5 C7 108.6(8) . . ? O2 C5 C6 105.6(5) . . ? C7 C5 C6 112.6(6) . . ? O2 C5 H5 110.0 . . ? C7 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5' O2' P1 111.2(8) . . ? O2' C5' C7' 104.8(8) . . ? O2' C5' C6' 107.7(11) . . ? C7' C5' C6' 103.7(12) . . ? O2' C5' H5' 113.3 . . ? C7' C5' H5' 113.3 . . ? C6' C5' H5' 113.3 . . ? C5' C6' H6'1 109.5 . . ? C5' C6' H6'2 109.5 . . ? H6'1 C6' H6'2 109.5 . . ? C5' C6' H6'3 109.5 . . ? H6'1 C6' H6'3 109.5 . . ? H6'2 C6' H6'3 109.5 . . ? C5' C7' H7'1 109.5 . . ? C5' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C5' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2' P1 N1 C1 -75.6(4) . . . . ? O1 P1 N1 C1 155.6(2) . . . . ? O2 P1 N1 C1 -104.6(3) . . . . ? S2 P1 N1 C1 22.5(3) . . . . ? S2' P1 N1 C1 35.7(3) . . . . ? O2' P1 N1 Ni1 93.9(3) . . . . ? O1 P1 N1 Ni1 -34.9(2) . . . . ? O2 P1 N1 Ni1 64.9(2) . . . . ? S2 P1 N1 Ni1 -168.04(16) . . . . ? S2' P1 N1 Ni1 -154.84(19) . . . . ? N1 Ni1 N1 C1 82(51) 2_656 . . . ? S1 Ni1 N1 C1 -3.70(14) . . . . ? S1 Ni1 N1 C1 176.30(14) 2_656 . . . ? N1 Ni1 N1 P1 -89(51) 2_656 . . . ? S1 Ni1 N1 P1 -175.39(19) . . . . ? S1 Ni1 N1 P1 4.61(19) 2_656 . . . ? P1 N1 C1 N2 -1.3(4) . . . . ? Ni1 N1 C1 N2 -173.5(2) . . . . ? P1 N1 C1 S1 177.07(15) . . . . ? Ni1 N1 C1 S1 4.87(18) . . . . ? N2 C1 S1 Ni1 174.1(2) . . . . ? N1 C1 S1 Ni1 -4.25(16) . . . . ? N1 Ni1 S1 C1 -177.08(11) 2_656 . . . ? N1 Ni1 S1 C1 2.92(11) . . . . ? S1 Ni1 S1 C1 -3(100) 2_656 . . . ? N1 C1 N2 C11 -172.5(2) . . . . ? S1 C1 N2 C11 9.4(4) . . . . ? C1 N2 C11 C16 97.8(3) . . . . ? C1 N2 C11 C12 -84.0(3) . . . . ? C16 C11 C12 C13 -1.5(4) . . . . ? N2 C11 C12 C13 -179.6(2) . . . . ? C16 C11 C12 C17 178.4(2) . . . . ? N2 C11 C12 C17 0.2(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C17 C12 C13 C14 -179.3(3) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C16 -0.3(4) . . . . ? C12 C11 C16 C15 1.5(4) . . . . ? N2 C11 C16 C15 179.6(2) . . . . ? C12 C11 C16 C18 -178.0(2) . . . . ? N2 C11 C16 C18 0.2(3) . . . . ? C14 C15 C16 C11 -0.6(4) . . . . ? C14 C15 C16 C18 178.9(3) . . . . ? O2' P1 O1 C2 135.3(3) . . . . ? N1 P1 O1 C2 -92.6(2) . . . . ? O2 P1 O1 C2 169.5(2) . . . . ? S2 P1 O1 C2 41.8(2) . . . . ? S2' P1 O1 C2 26.4(3) . . . . ? P1 O1 C2 C4 -165.1(2) . . . . ? P1 O1 C2 C3 71.3(3) . . . . ? O2' P1 O2 C5 29.8(5) . . . . ? O1 P1 O2 C5 -89.5(5) . . . . ? N1 P1 O2 C5 163.8(5) . . . . ? S2 P1 O2 C5 36.6(5) . . . . ? S2' P1 O2 C5 39.9(6) . . . . ? P1 O2 C5 C7 -145.4(4) . . . . ? P1 O2 C5 C6 93.6(5) . . . . ? O1 P1 O2' C5' 60.5(6) . . . . ? N1 P1 O2' C5' -64.6(6) . . . . ? O2 P1 O2' C5' -9.8(5) . . . . ? S2 P1 O2' C5' 176.3(6) . . . . ? S2' P1 O2' C5' 177.7(5) . . . . ? P1 O2' C5' C7' 115.2(9) . . . . ? P1 O2' C5' C6' -134.8(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S2 0.80(3) 2.48(3) 3.177(2) 146(3) . N2 H2 S2' 0.80(3) 2.49(3) 3.178(3) 145(3) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.560 _refine_diff_density_min -0.903 _refine_diff_density_rms 0.056 data_safin43 _database_code_depnum_ccdc_archive 'CCDC 736205' #TrackingRef '- HLII.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H23 N2 O2 P S2' _chemical_formula_sum 'C14 H23 N2 O2 P S2' _chemical_formula_weight 346.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9075(7) _cell_length_b 15.1449(7) _cell_length_c 12.9257(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.187(5) _cell_angle_gamma 90.00 _cell_volume 1808.38(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8900 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8572 _exptl_absorpt_correction_T_max 0.8827 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9964 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.61 _reflns_number_total 3372 _reflns_number_gt 2717 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0520P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3372 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.63052(5) 0.46319(3) 0.77343(4) 0.02682(13) Uani 1 1 d . . . S1 S 0.71938(5) 0.35502(3) 0.83979(4) 0.03667(14) Uani 1 1 d . . . S2 S 0.38285(5) 0.61488(3) 0.92180(4) 0.03057(13) Uani 1 1 d . . . N1 N 0.53724(16) 0.50659(10) 0.84669(14) 0.0280(3) Uani 1 1 d . . . H1 H 0.542(2) 0.4783(14) 0.9003(19) 0.034(6) Uiso 1 1 d . . . N2 N 0.47678(19) 0.64130(11) 0.75755(14) 0.0362(4) Uani 1 1 d . . . H2 H 0.526(3) 0.6270(17) 0.722(2) 0.058(8) Uiso 1 1 d . . . O1 O 0.52301(14) 0.46261(8) 0.64963(11) 0.0347(3) Uani 1 1 d . . . O2 O 0.72980(12) 0.53988(8) 0.75844(10) 0.0282(3) Uani 1 1 d . . . C1 C 0.46908(17) 0.58740(11) 0.83687(14) 0.0264(4) Uani 1 1 d . . . C2 C 0.4208(2) 0.39039(15) 0.60328(18) 0.0486(6) Uani 1 1 d . . . H2A H 0.4141 0.3523 0.6645 0.058 Uiso 1 1 calc R . . C3 C 0.4759(4) 0.33779(17) 0.5297(2) 0.0773(9) Uani 1 1 d . . . H3A H 0.5691 0.3113 0.5740 0.116 Uiso 1 1 calc R . . H3B H 0.4883 0.3764 0.4730 0.116 Uiso 1 1 calc R . . H3C H 0.4064 0.2910 0.4938 0.116 Uiso 1 1 calc R . . C4 C 0.2759(3) 0.4337(2) 0.5422(2) 0.0775(9) Uani 1 1 d . . . H4A H 0.2451 0.4668 0.5949 0.116 Uiso 1 1 calc R . . H4B H 0.2038 0.3882 0.5063 0.116 Uiso 1 1 calc R . . H4C H 0.2850 0.4740 0.4858 0.116 Uiso 1 1 calc R . . C5 C 0.87486(18) 0.55863(12) 0.84195(16) 0.0328(4) Uani 1 1 d . . . H5 H 0.9320 0.5026 0.8601 0.039 Uiso 1 1 calc R . . C6 C 0.8626(2) 0.59529(15) 0.94587(18) 0.0458(5) Uani 1 1 d . . . H6A H 0.8170 0.5514 0.9785 0.069 Uiso 1 1 calc R . . H6B H 0.8033 0.6490 0.9281 0.069 Uiso 1 1 calc R . . H6C H 0.9593 0.6095 0.9990 0.069 Uiso 1 1 calc R . . C7 C 0.9443(2) 0.62073(14) 0.7854(2) 0.0459(5) Uani 1 1 d . . . H7A H 0.9493 0.5925 0.7187 0.069 Uiso 1 1 calc R . . H7B H 1.0423 0.6353 0.8361 0.069 Uiso 1 1 calc R . . H7C H 0.8867 0.6749 0.7646 0.069 Uiso 1 1 calc R . . C11 C 0.4248(2) 0.73134(13) 0.74428(17) 0.0358(4) Uani 1 1 d . . . C12 C 0.2848(2) 0.75019(15) 0.67588(18) 0.0440(5) Uani 1 1 d . . . C13 C 0.2433(3) 0.84012(18) 0.6652(2) 0.0565(7) Uani 1 1 d . . . H13 H 0.1481 0.8561 0.6182 0.068 Uiso 1 1 calc R . . C14 C 0.3394(3) 0.90476(16) 0.7223(2) 0.0588(7) Uani 1 1 d . . . H14 H 0.3093 0.9647 0.7145 0.071 Uiso 1 1 calc R . . C15 C 0.4759(3) 0.88401(15) 0.7891(2) 0.0576(6) Uani 1 1 d . . . H15 H 0.5409 0.9292 0.8280 0.069 Uiso 1 1 calc R . . C16 C 0.5206(2) 0.79650(14) 0.8007(2) 0.0463(5) Uani 1 1 d . . . H16 H 0.6165 0.7815 0.8472 0.056 Uiso 1 1 calc R . . C17 C 0.1840(3) 0.6798(2) 0.6156(2) 0.0669(7) Uani 1 1 d . . . H17A H 0.2234 0.6492 0.5660 0.100 Uiso 1 1 calc R . . H17B H 0.0901 0.7059 0.5719 0.100 Uiso 1 1 calc R . . H17C H 0.1714 0.6376 0.6689 0.100 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 0.0296(2) 0.0267(2) 0.0238(2) -0.00001(18) 0.00933(19) 0.00093(17) S1 0.0454(3) 0.0281(2) 0.0370(3) 0.0030(2) 0.0155(2) 0.00712(19) S2 0.0324(2) 0.0334(2) 0.0304(2) 0.00647(19) 0.01672(19) 0.00475(17) N1 0.0331(8) 0.0265(7) 0.0263(8) 0.0052(7) 0.0129(7) 0.0020(6) N2 0.0456(10) 0.0369(9) 0.0346(9) 0.0141(7) 0.0248(8) 0.0153(7) O1 0.0388(7) 0.0355(7) 0.0245(7) -0.0030(5) 0.0051(6) -0.0043(5) O2 0.0245(6) 0.0329(6) 0.0260(7) 0.0036(5) 0.0078(5) 0.0001(5) C1 0.0238(8) 0.0301(8) 0.0234(9) 0.0022(7) 0.0064(7) -0.0003(6) C2 0.0559(13) 0.0543(13) 0.0290(11) -0.0012(10) 0.0075(9) -0.0274(10) C3 0.127(3) 0.0459(14) 0.0453(15) -0.0170(12) 0.0141(17) 0.0004(15) C4 0.0425(13) 0.122(3) 0.0569(17) 0.0030(17) 0.0047(12) -0.0217(15) C5 0.0232(8) 0.0333(9) 0.0362(11) 0.0038(8) 0.0039(8) 0.0041(7) C6 0.0416(11) 0.0522(13) 0.0343(11) -0.0045(10) 0.0026(9) -0.0006(9) C7 0.0354(10) 0.0448(11) 0.0549(14) 0.0062(10) 0.0132(10) -0.0050(8) C11 0.0407(10) 0.0413(11) 0.0342(10) 0.0184(9) 0.0239(9) 0.0160(8) C12 0.0414(11) 0.0591(13) 0.0369(12) 0.0149(10) 0.0207(9) 0.0145(9) C13 0.0585(14) 0.0712(17) 0.0478(14) 0.0290(12) 0.0289(12) 0.0379(13) C14 0.0800(17) 0.0463(13) 0.0640(17) 0.0232(12) 0.0429(15) 0.0273(13) C15 0.0730(16) 0.0397(12) 0.0681(17) 0.0133(11) 0.0349(14) 0.0080(11) C16 0.0482(12) 0.0405(11) 0.0546(14) 0.0153(10) 0.0237(11) 0.0082(9) C17 0.0523(14) 0.088(2) 0.0534(16) 0.0073(14) 0.0102(13) 0.0046(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5695(13) . ? P1 O2 1.5786(12) . ? P1 N1 1.6779(16) . ? P1 S1 1.9102(7) . ? S2 C1 1.6691(18) . ? N1 C1 1.381(2) . ? N1 H1 0.80(2) . ? N2 C1 1.334(2) . ? N2 C11 1.446(2) . ? N2 H2 0.81(3) . ? O1 C2 1.464(2) . ? O2 C5 1.480(2) . ? C2 C3 1.487(4) . ? C2 C4 1.515(4) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.499(3) . ? C5 C7 1.502(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C12 1.378(3) . ? C11 C16 1.381(3) . ? C12 C13 1.415(3) . ? C12 C17 1.476(4) . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.352(4) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 95.88(7) . . ? O1 P1 N1 105.57(8) . . ? O2 P1 N1 106.01(7) . . ? O1 P1 S1 119.07(5) . . ? O2 P1 S1 118.66(5) . . ? N1 P1 S1 109.94(6) . . ? C1 N1 P1 130.23(14) . . ? C1 N1 H1 115.5(15) . . ? P1 N1 H1 113.8(15) . . ? C1 N2 C11 123.46(16) . . ? C1 N2 H2 119.2(18) . . ? C11 N2 H2 116.4(18) . . ? C2 O1 P1 122.40(12) . . ? C5 O2 P1 122.39(11) . . ? N2 C1 N1 116.81(16) . . ? N2 C1 S2 122.53(14) . . ? N1 C1 S2 120.66(13) . . ? O1 C2 C3 107.6(2) . . ? O1 C2 C4 106.0(2) . . ? C3 C2 C4 113.3(2) . . ? O1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C4 C2 H2A 109.9 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C6 110.65(15) . . ? O2 C5 C7 105.08(15) . . ? C6 C5 C7 113.84(18) . . ? O2 C5 H5 109.0 . . ? C6 C5 H5 109.0 . . ? C7 C5 H5 109.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C16 122.09(19) . . ? C12 C11 N2 120.3(2) . . ? C16 C11 N2 117.62(17) . . ? C11 C12 C13 116.9(2) . . ? C11 C12 C17 121.4(2) . . ? C13 C12 C17 121.7(2) . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 119.8(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 119.5(2) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 N1 C1 -57.87(17) . . . . ? O2 P1 N1 C1 43.11(17) . . . . ? S1 P1 N1 C1 172.52(14) . . . . ? O2 P1 O1 C2 165.85(15) . . . . ? N1 P1 O1 C2 -85.70(16) . . . . ? S1 P1 O1 C2 38.35(17) . . . . ? O1 P1 O2 C5 -165.23(13) . . . . ? N1 P1 O2 C5 86.70(13) . . . . ? S1 P1 O2 C5 -37.43(14) . . . . ? C11 N2 C1 N1 -173.16(17) . . . . ? C11 N2 C1 S2 6.5(3) . . . . ? P1 N1 C1 N2 -0.2(3) . . . . ? P1 N1 C1 S2 -179.83(10) . . . . ? P1 O1 C2 C3 -106.02(19) . . . . ? P1 O1 C2 C4 132.44(17) . . . . ? P1 O2 C5 C6 -69.05(18) . . . . ? P1 O2 C5 C7 167.65(12) . . . . ? C1 N2 C11 C12 -91.4(2) . . . . ? C1 N2 C11 C16 89.6(2) . . . . ? C16 C11 C12 C13 0.4(3) . . . . ? N2 C11 C12 C13 -178.51(17) . . . . ? C16 C11 C12 C17 179.6(2) . . . . ? N2 C11 C12 C17 0.7(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C17 C12 C13 C14 -179.9(2) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? N2 C11 C16 C15 179.07(19) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.80(2) 2.57(2) 3.3545(17) 167.6(19) 3_667 N2 H2 O1 0.81(3) 2.66(3) 3.153(2) 121(2) . N2 H2 O1 0.81(3) 2.66(3) 3.153(2) 121(2) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.242 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.046 data_safin36 _database_code_depnum_ccdc_archive 'CCDC 736206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H27 N2 O2 P S2' _chemical_formula_sum 'C16 H27 N2 O2 P S2' _chemical_formula_weight 374.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6196(9) _cell_length_b 10.0482(8) _cell_length_c 10.6353(10) _cell_angle_alpha 82.561(7) _cell_angle_beta 88.528(7) _cell_angle_gamma 75.021(7) _cell_volume 984.68(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8604 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 25.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8457 _exptl_absorpt_correction_T_max 0.8543 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9742 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.73 _reflns_number_total 3666 _reflns_number_gt 3248 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.5867P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3666 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.32965(4) 0.78600(4) 0.37303(4) 0.01809(13) Uani 1 1 d . . . S1 S 0.38229(5) 0.59444(4) 0.34193(4) 0.02669(14) Uani 1 1 d . . . O1 O 0.44680(12) 0.83170(12) 0.44491(11) 0.0226(3) Uani 1 1 d . . . O2 O 0.28583(13) 0.89900(12) 0.25438(10) 0.0222(3) Uani 1 1 d . . . N1 N 0.18633(15) 0.83337(15) 0.46481(13) 0.0207(3) Uani 1 1 d . . . H1 H 0.128(2) 0.910(2) 0.440(2) 0.034(6) Uiso 1 1 d . . . N2 N 0.24825(16) 0.65317(15) 0.62842(14) 0.0229(3) Uani 1 1 d . . . H2 H 0.305(2) 0.614(2) 0.579(2) 0.026(5) Uiso 1 1 d . . . C1 C 0.16175(17) 0.77751(17) 0.58646(15) 0.0202(3) Uani 1 1 d . . . S2 S 0.02861(5) 0.86278(5) 0.67293(4) 0.02970(14) Uani 1 1 d . . . C2 C 0.60158(19) 0.7923(2) 0.41560(18) 0.0295(4) Uani 1 1 d . . . H2A H 0.6284 0.6969 0.3895 0.035 Uiso 1 1 calc R . . C3 C 0.6323(3) 0.8944(4) 0.3095(3) 0.0794(11) Uani 1 1 d . . . H3A H 0.5814 0.8884 0.2326 0.119 Uiso 1 1 calc R . . H3B H 0.7360 0.8730 0.2936 0.119 Uiso 1 1 calc R . . H3C H 0.5994 0.9886 0.3329 0.119 Uiso 1 1 calc R . . C4 C 0.6788(2) 0.7922(2) 0.5362(2) 0.0404(5) Uani 1 1 d . . . H4A H 0.6485 0.8846 0.5639 0.061 Uiso 1 1 calc R . . H4B H 0.7828 0.7683 0.5217 0.061 Uiso 1 1 calc R . . H4C H 0.6555 0.7236 0.6019 0.061 Uiso 1 1 calc R . . C5 C 0.2566(2) 0.86999(19) 0.12707(16) 0.0277(4) Uani 1 1 d . . . H5 H 0.3321 0.7874 0.1053 0.033 Uiso 1 1 calc R . . C6 C 0.1121(3) 0.8416(2) 0.1227(2) 0.0456(5) Uani 1 1 d . . . H6A H 0.1102 0.7595 0.1827 0.068 Uiso 1 1 calc R . . H6B H 0.0931 0.8248 0.0368 0.068 Uiso 1 1 calc R . . H6C H 0.0383 0.9218 0.1456 0.068 Uiso 1 1 calc R . . C7 C 0.2687(3) 0.9973(2) 0.03914(19) 0.0458(6) Uani 1 1 d . . . H7A H 0.1950 1.0784 0.0606 0.069 Uiso 1 1 calc R . . H7B H 0.2547 0.9835 -0.0487 0.069 Uiso 1 1 calc R . . H7C H 0.3643 1.0126 0.0486 0.069 Uiso 1 1 calc R . . C11 C 0.23658(18) 0.58023(16) 0.75261(15) 0.0200(3) Uani 1 1 d . . . C12 C 0.15204(19) 0.48622(18) 0.76774(16) 0.0234(4) Uani 1 1 d . . . C13 C 0.14456(19) 0.41534(18) 0.88873(17) 0.0250(4) Uani 1 1 d . . . H13 H 0.0876 0.3504 0.9010 0.030 Uiso 1 1 calc R . . C14 C 0.21825(18) 0.43736(17) 0.99156(16) 0.0221(4) Uani 1 1 d . . . C15 C 0.30193(18) 0.53185(17) 0.97164(15) 0.0214(3) Uani 1 1 d . . . H15 H 0.3530 0.5475 1.0413 0.026 Uiso 1 1 calc R . . C16 C 0.31330(18) 0.60438(16) 0.85275(16) 0.0208(3) Uani 1 1 d . . . C17 C 0.0654(2) 0.4669(2) 0.65853(18) 0.0332(4) Uani 1 1 d . . . H17A H -0.0149 0.5494 0.6390 0.050 Uiso 1 1 calc R . . H17B H 0.0279 0.3852 0.6816 0.050 Uiso 1 1 calc R . . H17C H 0.1270 0.4535 0.5840 0.050 Uiso 1 1 calc R . . C18 C 0.2067(2) 0.3611(2) 1.12191(17) 0.0297(4) Uani 1 1 d . . . H18A H 0.2844 0.2754 1.1342 0.044 Uiso 1 1 calc R . . H18B H 0.1136 0.3382 1.1298 0.044 Uiso 1 1 calc R . . H18C H 0.2147 0.4202 1.1864 0.044 Uiso 1 1 calc R . . C19 C 0.4027(2) 0.70759(19) 0.83243(18) 0.0302(4) Uani 1 1 d . . . H19A H 0.4521 0.7082 0.9117 0.045 Uiso 1 1 calc R . . H19B H 0.3403 0.8003 0.8057 0.045 Uiso 1 1 calc R . . H19C H 0.4741 0.6816 0.7666 0.045 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 0.0205(2) 0.0176(2) 0.0139(2) -0.00065(15) 0.00156(15) -0.00167(16) S1 0.0355(3) 0.0187(2) 0.0231(2) -0.00356(16) 0.00157(18) -0.00172(17) O1 0.0196(6) 0.0259(6) 0.0213(6) -0.0051(5) 0.0011(5) -0.0030(5) O2 0.0312(7) 0.0203(6) 0.0133(6) 0.0006(4) 0.0003(5) -0.0047(5) N1 0.0203(7) 0.0200(7) 0.0165(7) 0.0034(5) 0.0024(5) 0.0015(6) N2 0.0240(7) 0.0223(7) 0.0155(7) 0.0022(6) 0.0048(6) 0.0038(6) C1 0.0196(8) 0.0222(8) 0.0168(8) 0.0001(6) 0.0010(6) -0.0033(6) S2 0.0269(2) 0.0283(2) 0.0230(2) 0.00571(17) 0.00900(17) 0.00716(18) C2 0.0183(9) 0.0359(10) 0.0314(10) -0.0032(8) 0.0023(7) -0.0025(7) C3 0.0359(14) 0.123(3) 0.0620(18) 0.0463(18) 0.0091(12) -0.0184(15) C4 0.0275(10) 0.0491(12) 0.0453(12) -0.0106(10) -0.0076(9) -0.0083(9) C5 0.0396(10) 0.0268(9) 0.0138(8) -0.0030(7) -0.0008(7) -0.0027(8) C6 0.0497(13) 0.0472(13) 0.0418(12) -0.0033(10) -0.0173(10) -0.0150(11) C7 0.0673(16) 0.0419(12) 0.0219(10) 0.0088(9) 0.0024(10) -0.0091(11) C11 0.0210(8) 0.0178(8) 0.0155(8) 0.0027(6) 0.0026(6) 0.0024(6) C12 0.0230(8) 0.0250(8) 0.0197(8) -0.0019(7) -0.0021(7) -0.0021(7) C13 0.0266(9) 0.0255(8) 0.0235(9) 0.0019(7) -0.0016(7) -0.0100(7) C14 0.0230(8) 0.0222(8) 0.0181(8) 0.0012(6) 0.0021(6) -0.0026(7) C15 0.0243(8) 0.0221(8) 0.0166(8) -0.0020(6) -0.0019(6) -0.0037(7) C16 0.0210(8) 0.0176(8) 0.0216(8) -0.0010(6) 0.0020(6) -0.0017(6) C17 0.0339(10) 0.0438(11) 0.0229(9) -0.0034(8) -0.0068(8) -0.0114(9) C18 0.0340(10) 0.0334(10) 0.0209(9) 0.0046(7) -0.0002(7) -0.0114(8) C19 0.0373(10) 0.0273(9) 0.0277(9) 0.0007(7) 0.0015(8) -0.0136(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5709(12) . ? P1 O2 1.5710(11) . ? P1 N1 1.6709(15) . ? P1 S1 1.9296(6) . ? O1 C2 1.474(2) . ? O2 C5 1.470(2) . ? N1 C1 1.382(2) . ? N1 H1 0.84(2) . ? N2 C1 1.338(2) . ? N2 C11 1.442(2) . ? N2 H2 0.81(2) . ? C1 S2 1.6722(17) . ? C2 C4 1.498(3) . ? C2 C3 1.502(3) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.492(3) . ? C5 C7 1.512(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C12 1.389(2) . ? C11 C16 1.392(2) . ? C12 C13 1.397(2) . ? C12 C17 1.508(2) . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C14 C15 1.389(2) . ? C14 C18 1.511(2) . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 C19 1.502(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 105.15(6) . . ? O1 P1 N1 101.15(7) . . ? O2 P1 N1 100.24(7) . . ? O1 P1 S1 114.90(5) . . ? O2 P1 S1 116.87(5) . . ? N1 P1 S1 116.29(6) . . ? C2 O1 P1 123.58(11) . . ? C5 O2 P1 124.79(11) . . ? C1 N1 P1 128.89(12) . . ? C1 N1 H1 114.1(16) . . ? P1 N1 H1 115.8(15) . . ? C1 N2 C11 123.38(15) . . ? C1 N2 H2 117.7(14) . . ? C11 N2 H2 118.7(14) . . ? N2 C1 N1 116.36(15) . . ? N2 C1 S2 123.11(13) . . ? N1 C1 S2 120.52(12) . . ? O1 C2 C4 105.94(15) . . ? O1 C2 C3 108.98(16) . . ? C4 C2 C3 112.9(2) . . ? O1 C2 H2A 109.7 . . ? C4 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C6 110.35(16) . . ? O2 C5 C7 104.93(15) . . ? C6 C5 C7 113.25(17) . . ? O2 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C7 C5 H5 109.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C16 122.30(15) . . ? C12 C11 N2 119.05(15) . . ? C16 C11 N2 118.63(15) . . ? C11 C12 C13 117.83(16) . . ? C11 C12 C17 120.95(15) . . ? C13 C12 C17 121.16(16) . . ? C14 C13 C12 121.74(16) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 118.34(15) . . ? C13 C14 C18 120.78(16) . . ? C15 C14 C18 120.87(16) . . ? C14 C15 C16 121.99(16) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C11 117.79(15) . . ? C15 C16 C19 121.61(16) . . ? C11 C16 C19 120.58(15) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C2 -86.78(13) . . . . ? N1 P1 O1 C2 169.27(12) . . . . ? S1 P1 O1 C2 43.16(13) . . . . ? O1 P1 O2 C5 140.54(13) . . . . ? N1 P1 O2 C5 -114.84(14) . . . . ? S1 P1 O2 C5 11.76(15) . . . . ? O1 P1 N1 C1 -69.12(16) . . . . ? O2 P1 N1 C1 -176.96(15) . . . . ? S1 P1 N1 C1 56.06(17) . . . . ? C11 N2 C1 N1 -179.66(15) . . . . ? C11 N2 C1 S2 -0.5(2) . . . . ? P1 N1 C1 N2 -14.8(2) . . . . ? P1 N1 C1 S2 165.97(10) . . . . ? P1 O1 C2 C4 -152.67(13) . . . . ? P1 O1 C2 C3 85.6(2) . . . . ? P1 O2 C5 C6 76.04(18) . . . . ? P1 O2 C5 C7 -161.65(14) . . . . ? C1 N2 C11 C12 92.2(2) . . . . ? C1 N2 C11 C16 -89.3(2) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? N2 C11 C12 C13 178.98(15) . . . . ? C16 C11 C12 C17 177.43(16) . . . . ? N2 C11 C12 C17 -4.1(2) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C17 C12 C13 C14 -176.76(17) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C12 C13 C14 C18 179.07(17) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C18 C14 C15 C16 -179.41(16) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C14 C15 C16 C19 179.28(17) . . . . ? C12 C11 C16 C15 -0.8(2) . . . . ? N2 C11 C16 C15 -179.30(14) . . . . ? C12 C11 C16 C19 -179.62(16) . . . . ? N2 C11 C16 C19 1.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.84(2) 2.55(2) 3.3878(15) 170(2) 2_576 N2 H2 S1 0.81(2) 2.62(2) 3.3415(16) 147.9(18) . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.245 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.049 data_safin34 _database_code_depnum_ccdc_archive 'CCDC 736207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H19 N2 O2 P S2' _chemical_formula_sum 'C8 H19 N2 O2 P S2' _chemical_formula_weight 270.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4084(7) _cell_length_b 9.7510(8) _cell_length_c 10.2595(9) _cell_angle_alpha 80.832(7) _cell_angle_beta 76.351(7) _cell_angle_gamma 70.632(7) _cell_volume 676.79(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4695 _cell_measurement_theta_min 4.0 _cell_measurement_theta_max 25.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.497 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8036 _exptl_absorpt_correction_T_max 0.8452 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5904 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 25.58 _reflns_number_total 2507 _reflns_number_gt 2413 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0414P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.045(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2507 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.64982(5) 0.67401(4) 0.29149(4) 0.01670(13) Uani 1 1 d . . . S1 S 0.70331(6) 0.67312(4) 0.46559(4) 0.02663(14) Uani 1 1 d . . . S2 S 1.02809(6) 0.29115(4) 0.10595(4) 0.02465(14) Uani 1 1 d . . . O1 O 0.64978(16) 0.81163(11) 0.18798(10) 0.0218(2) Uani 1 1 d . . . O2 O 0.44663(15) 0.64818(12) 0.30766(10) 0.0211(2) Uani 1 1 d . . . N1 N 0.81190(19) 0.54755(14) 0.19411(13) 0.0203(3) Uani 1 1 d . . . H1 H 0.855(3) 0.577(2) 0.123(2) 0.027(5) Uiso 1 1 d . . . N2 N 0.8202(2) 0.34779(15) 0.34987(14) 0.0284(3) Uani 1 1 d . . . H2 H 0.756(3) 0.407(2) 0.408(2) 0.039(6) Uiso 1 1 d . . . C1 C 0.8791(2) 0.39901(16) 0.22511(15) 0.0191(3) Uani 1 1 d . . . C2 C 0.8781(3) 0.19467(18) 0.39952(18) 0.0339(4) Uani 1 1 d . . . H2A H 0.8719 0.1356 0.3328 0.051 Uiso 1 1 calc R . . H2B H 0.7896 0.1796 0.4842 0.051 Uiso 1 1 calc R . . H2C H 1.0118 0.1655 0.4150 0.051 Uiso 1 1 calc R . . C3 C 0.6414(2) 0.95371(16) 0.22492(16) 0.0232(3) Uani 1 1 d . . . H3 H 0.7354 0.9385 0.2855 0.028 Uiso 1 1 calc R . . C4 C 0.7039(3) 1.03712(19) 0.09469(19) 0.0330(4) Uani 1 1 d . . . H4A H 0.8307 0.9785 0.0475 0.050 Uiso 1 1 calc R . . H4B H 0.7149 1.1290 0.1140 0.050 Uiso 1 1 calc R . . H4C H 0.6069 1.0580 0.0379 0.050 Uiso 1 1 calc R . . C5 C 0.4381(3) 1.0294(2) 0.2964(2) 0.0403(5) Uani 1 1 d . . . H5A H 0.4020 0.9683 0.3774 0.060 Uiso 1 1 calc R . . H5B H 0.3464 1.0460 0.2364 0.060 Uiso 1 1 calc R . . H5C H 0.4337 1.1233 0.3220 0.060 Uiso 1 1 calc R . . C6 C 0.3647(2) 0.64976(18) 0.18883(15) 0.0240(3) Uani 1 1 d . . . H6 H 0.4476 0.6819 0.1056 0.029 Uiso 1 1 calc R . . C7 C 0.1637(3) 0.7589(2) 0.2096(2) 0.0372(4) Uani 1 1 d . . . H7A H 0.1735 0.8554 0.2155 0.056 Uiso 1 1 calc R . . H7B H 0.0842 0.7293 0.2932 0.056 Uiso 1 1 calc R . . H7C H 0.1025 0.7629 0.1336 0.056 Uiso 1 1 calc R . . C8 C 0.3646(3) 0.4972(2) 0.1795(2) 0.0395(4) Uani 1 1 d . . . H8A H 0.4984 0.4309 0.1699 0.059 Uiso 1 1 calc R . . H8B H 0.3112 0.4959 0.1011 0.059 Uiso 1 1 calc R . . H8C H 0.2840 0.4656 0.2614 0.059 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 0.0181(2) 0.0156(2) 0.0149(2) -0.00323(14) -0.00017(14) -0.00435(14) S1 0.0329(2) 0.0291(2) 0.0184(2) -0.00513(15) -0.00674(16) -0.00761(17) S2 0.0304(2) 0.0173(2) 0.0204(2) -0.00516(14) 0.00283(16) -0.00338(16) O1 0.0303(6) 0.0151(5) 0.0194(5) -0.0030(4) -0.0021(4) -0.0075(4) O2 0.0196(5) 0.0272(6) 0.0164(5) -0.0026(4) -0.0005(4) -0.0086(4) N1 0.0229(7) 0.0170(6) 0.0160(6) -0.0010(5) 0.0029(5) -0.0042(5) N2 0.0343(8) 0.0177(7) 0.0214(7) -0.0009(5) 0.0062(6) -0.0010(6) C1 0.0169(7) 0.0189(7) 0.0207(7) -0.0027(6) -0.0015(6) -0.0056(5) C2 0.0409(10) 0.0203(8) 0.0279(9) 0.0043(7) 0.0046(7) -0.0037(7) C3 0.0281(8) 0.0145(7) 0.0288(8) -0.0055(6) -0.0058(6) -0.0070(6) C4 0.0381(10) 0.0234(8) 0.0381(10) 0.0015(7) -0.0034(8) -0.0149(7) C5 0.0404(11) 0.0280(9) 0.0398(10) -0.0111(8) 0.0053(8) 0.0006(8) C6 0.0256(8) 0.0309(8) 0.0183(7) -0.0001(6) -0.0048(6) -0.0127(6) C7 0.0241(9) 0.0492(11) 0.0389(10) -0.0025(8) -0.0104(7) -0.0099(8) C8 0.0575(13) 0.0374(10) 0.0339(10) -0.0031(8) -0.0151(9) -0.0237(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5730(11) . ? P1 O2 1.5739(11) . ? P1 N1 1.6748(13) . ? P1 S1 1.9169(5) . ? S2 C1 1.6799(15) . ? O1 C3 1.4717(17) . ? O2 C6 1.4805(18) . ? N1 C1 1.377(2) . ? N1 H1 0.78(2) . ? N2 C1 1.325(2) . ? N2 C2 1.452(2) . ? N2 H2 0.84(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C5 1.505(2) . ? C3 C4 1.508(2) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.505(2) . ? C6 C8 1.506(2) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 107.11(6) . . ? O1 P1 N1 97.97(6) . . ? O2 P1 N1 106.25(6) . . ? O1 P1 S1 118.71(5) . . ? O2 P1 S1 109.71(4) . . ? N1 P1 S1 115.86(5) . . ? C3 O1 P1 123.90(10) . . ? C6 O2 P1 121.26(9) . . ? C1 N1 P1 128.21(11) . . ? C1 N1 H1 116.2(15) . . ? P1 N1 H1 115.6(15) . . ? C1 N2 C2 124.42(14) . . ? C1 N2 H2 118.8(15) . . ? C2 N2 H2 116.3(15) . . ? N2 C1 N1 117.32(14) . . ? N2 C1 S2 122.92(12) . . ? N1 C1 S2 119.76(11) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C5 109.76(13) . . ? O1 C3 C4 105.77(13) . . ? C5 C3 C4 112.75(15) . . ? O1 C3 H3 109.5 . . ? C5 C3 H3 109.5 . . ? C4 C3 H3 109.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 C7 106.44(13) . . ? O2 C6 C8 108.20(13) . . ? C7 C6 C8 113.40(15) . . ? O2 C6 H6 109.6 . . ? C7 C6 H6 109.6 . . ? C8 C6 H6 109.6 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C3 109.54(12) . . . . ? N1 P1 O1 C3 -140.66(12) . . . . ? S1 P1 O1 C3 -15.28(13) . . . . ? O1 P1 O2 C6 47.32(12) . . . . ? N1 P1 O2 C6 -56.62(12) . . . . ? S1 P1 O2 C6 177.42(10) . . . . ? O1 P1 N1 C1 -179.70(14) . . . . ? O2 P1 N1 C1 -69.20(15) . . . . ? S1 P1 N1 C1 52.93(15) . . . . ? C2 N2 C1 N1 -179.53(16) . . . . ? C2 N2 C1 S2 1.0(2) . . . . ? P1 N1 C1 N2 -4.9(2) . . . . ? P1 N1 C1 S2 174.65(8) . . . . ? P1 O1 C3 C5 -74.47(17) . . . . ? P1 O1 C3 C4 163.63(11) . . . . ? P1 O2 C6 C7 -125.92(12) . . . . ? P1 O2 C6 C8 111.88(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.78(2) 2.59(2) 3.3656(14) 172.4(19) 2_765 N2 H2 S1 0.84(2) 2.63(2) 3.3341(15) 141.6(19) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.428 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.054 data_safin42 _database_code_depnum_ccdc_archive 'CCDC 736208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H44 N4 Ni O4 P2 S4' _chemical_formula_sum 'C28 H44 N4 Ni O4 P2 S4' _chemical_formula_weight 749.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3222(8) _cell_length_b 9.3599(10) _cell_length_c 12.9907(13) _cell_angle_alpha 103.075(8) _cell_angle_beta 105.168(8) _cell_angle_gamma 106.810(8) _cell_volume 883.60(18) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6386 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 25.8 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 0.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7285 _exptl_absorpt_correction_T_max 0.8676 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7372 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 25.59 _reflns_number_total 3270 _reflns_number_gt 2919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.047(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3270 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.5000 0.5000 1.0000 0.01744(15) Uani 1 2 d S . . P1 P 0.53322(7) 0.60121(5) 0.78377(4) 0.01778(16) Uani 1 1 d . . . S1 S 0.24073(7) 0.29658(6) 0.91200(4) 0.02357(16) Uani 1 1 d . . . S2 S 0.43484(7) 0.53821(6) 0.62029(4) 0.02695(17) Uani 1 1 d . . . N1 N 0.4395(2) 0.48004(19) 0.84389(14) 0.0203(4) Uani 1 1 d . . . N2 N 0.1869(2) 0.28486(19) 0.69284(14) 0.0220(4) Uani 1 1 d D . . H2 H 0.236(3) 0.331(3) 0.6493(19) 0.039(7) Uiso 1 1 d D . . O1 O 0.52444(18) 0.76028(15) 0.84978(11) 0.0212(3) Uani 1 1 d . . . O2 O 0.74080(18) 0.63464(15) 0.83018(11) 0.0211(3) Uani 1 1 d . . . C1 C 0.2850(3) 0.3525(2) 0.80152(17) 0.0192(4) Uani 1 1 d . . . C2 C 0.5925(3) 0.9062(2) 0.82275(18) 0.0249(4) Uani 1 1 d . . . H2A H 0.5998 0.8782 0.7456 0.030 Uiso 1 1 calc R . . C3 C 0.7766(3) 1.0049(3) 0.9078(2) 0.0428(6) Uani 1 1 d . . . H3A H 0.8572 0.9477 0.9015 0.064 Uiso 1 1 calc R . . H3B H 0.7709 1.0268 0.9839 0.064 Uiso 1 1 calc R . . H3C H 0.8218 1.1047 0.8935 0.064 Uiso 1 1 calc R . . C4 C 0.4569(4) 0.9829(3) 0.8236(3) 0.0441(6) Uani 1 1 d . . . H4A H 0.3410 0.9119 0.7658 0.066 Uiso 1 1 calc R . . H4B H 0.4969 1.0821 0.8076 0.066 Uiso 1 1 calc R . . H4C H 0.4445 1.0049 0.8979 0.066 Uiso 1 1 calc R . . C5 C 0.8249(3) 0.5360(2) 0.7776(2) 0.0287(5) Uani 1 1 d . . . H5 H 0.7815 0.5171 0.6945 0.034 Uiso 1 1 calc R . . C6 C 0.7731(4) 0.3793(3) 0.7971(3) 0.0529(8) Uani 1 1 d . . . H6A H 0.6426 0.3251 0.7643 0.079 Uiso 1 1 calc R . . H6B H 0.8132 0.3962 0.8784 0.079 Uiso 1 1 calc R . . H6C H 0.8299 0.3145 0.7614 0.079 Uiso 1 1 calc R . . C7 C 1.0222(3) 0.6307(3) 0.8253(3) 0.0477(7) Uani 1 1 d . . . H7A H 1.0450 0.7310 0.8097 0.072 Uiso 1 1 calc R . . H7B H 1.0846 0.5714 0.7903 0.072 Uiso 1 1 calc R . . H7C H 1.0661 0.6518 0.9070 0.072 Uiso 1 1 calc R . . C11 C 0.0209(3) 0.1525(2) 0.64232(16) 0.0204(4) Uani 1 1 d . . . C12 C -0.1126(3) 0.1592(2) 0.55417(17) 0.0242(4) Uani 1 1 d . . . C13 C -0.2732(3) 0.0282(3) 0.50304(19) 0.0312(5) Uani 1 1 d . . . H13 H -0.3661 0.0300 0.4431 0.037 Uiso 1 1 calc R . . C14 C -0.3011(3) -0.1039(3) 0.5369(2) 0.0332(5) Uani 1 1 d . . . H14 H -0.4122 -0.1909 0.5010 0.040 Uiso 1 1 calc R . . C15 C -0.1660(3) -0.1087(2) 0.62360(19) 0.0291(5) Uani 1 1 d . . . H15 H -0.1840 -0.1992 0.6472 0.035 Uiso 1 1 calc R . . C16 C -0.0041(3) 0.0195(2) 0.67582(17) 0.0239(4) Uani 1 1 d . . . H16 H 0.0894 0.0160 0.7344 0.029 Uiso 1 1 calc R . . C17 C -0.0864(3) 0.3011(3) 0.5151(2) 0.0344(5) Uani 1 1 d . . . H17A H -0.0415 0.3970 0.5804 0.052 Uiso 1 1 calc R . . H17B H -0.2010 0.2915 0.4631 0.052 Uiso 1 1 calc R . . H17C H 0.0005 0.3073 0.4763 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0190(2) 0.0157(2) 0.0162(2) 0.00846(14) 0.00510(15) 0.00298(14) P1 0.0211(3) 0.0146(3) 0.0172(3) 0.0078(2) 0.0065(2) 0.0041(2) S1 0.0233(3) 0.0223(3) 0.0203(3) 0.0106(2) 0.0063(2) 0.0001(2) S2 0.0335(3) 0.0238(3) 0.0174(3) 0.0096(2) 0.0062(2) 0.0021(2) N1 0.0224(8) 0.0182(8) 0.0190(8) 0.0108(7) 0.0068(7) 0.0025(7) N2 0.0236(9) 0.0175(8) 0.0194(9) 0.0087(7) 0.0043(7) 0.0005(7) O1 0.0257(7) 0.0157(7) 0.0253(7) 0.0103(6) 0.0112(6) 0.0072(5) O2 0.0222(7) 0.0171(6) 0.0245(7) 0.0074(5) 0.0094(6) 0.0065(5) C1 0.0216(10) 0.0151(9) 0.0223(10) 0.0095(7) 0.0065(8) 0.0073(7) C2 0.0321(11) 0.0164(9) 0.0316(11) 0.0135(8) 0.0148(9) 0.0086(8) C3 0.0371(14) 0.0212(11) 0.0540(16) 0.0104(11) 0.0068(12) -0.0023(10) C4 0.0476(15) 0.0355(13) 0.0681(18) 0.0304(13) 0.0273(14) 0.0252(11) C5 0.0319(12) 0.0253(11) 0.0364(12) 0.0116(9) 0.0186(10) 0.0141(9) C6 0.0677(19) 0.0328(13) 0.086(2) 0.0306(14) 0.0452(18) 0.0318(13) C7 0.0296(13) 0.0460(15) 0.0679(19) 0.0116(14) 0.0210(13) 0.0165(11) C11 0.0214(10) 0.0171(9) 0.0214(10) 0.0052(8) 0.0089(8) 0.0050(8) C12 0.0259(10) 0.0242(10) 0.0220(10) 0.0065(8) 0.0077(9) 0.0100(8) C13 0.0221(11) 0.0340(12) 0.0267(11) 0.0046(9) 0.0023(9) 0.0052(9) C14 0.0241(11) 0.0262(11) 0.0355(13) 0.0001(9) 0.0098(10) -0.0017(9) C15 0.0337(12) 0.0189(10) 0.0330(12) 0.0081(9) 0.0163(10) 0.0037(8) C16 0.0255(10) 0.0187(9) 0.0258(10) 0.0094(8) 0.0076(9) 0.0053(8) C17 0.0375(13) 0.0291(11) 0.0326(12) 0.0134(10) 0.0024(10) 0.0131(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.9082(16) . ? Ni1 N1 1.9082(16) 2_667 ? Ni1 S1 2.2217(6) 2_667 ? Ni1 S1 2.2217(6) . ? Ni1 C1 2.510(2) . ? Ni1 C1 2.510(2) 2_667 ? P1 O1 1.5733(14) . ? P1 O2 1.5819(15) . ? P1 N1 1.6468(16) . ? P1 S2 1.9423(7) . ? S1 C1 1.725(2) . ? N1 C1 1.351(3) . ? N2 C1 1.324(3) . ? N2 C11 1.429(3) . ? N2 H2 0.896(10) . ? O1 C2 1.478(2) . ? O2 C5 1.466(2) . ? C2 C3 1.502(3) . ? C2 C4 1.503(3) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.498(3) . ? C5 C6 1.503(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C16 1.388(3) . ? C11 C12 1.398(3) . ? C12 C13 1.396(3) . ? C12 C17 1.506(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 180.00(10) . 2_667 ? N1 Ni1 S1 105.73(5) . 2_667 ? N1 Ni1 S1 74.28(5) 2_667 2_667 ? N1 Ni1 S1 74.28(5) . . ? N1 Ni1 S1 105.72(5) 2_667 . ? S1 Ni1 S1 180.0 2_667 . ? N1 Ni1 C1 32.09(6) . . ? N1 Ni1 C1 147.91(7) 2_667 . ? S1 Ni1 C1 137.80(5) 2_667 . ? S1 Ni1 C1 42.20(5) . . ? N1 Ni1 C1 147.91(7) . 2_667 ? N1 Ni1 C1 32.09(6) 2_667 2_667 ? S1 Ni1 C1 42.20(5) 2_667 2_667 ? S1 Ni1 C1 137.80(5) . 2_667 ? C1 Ni1 C1 180.00(9) . 2_667 ? O1 P1 O2 102.07(8) . . ? O1 P1 N1 101.20(8) . . ? O2 P1 N1 106.14(8) . . ? O1 P1 S2 115.72(6) . . ? O2 P1 S2 112.80(6) . . ? N1 P1 S2 117.15(7) . . ? C1 S1 Ni1 77.89(7) . . ? C1 N1 P1 130.86(14) . . ? C1 N1 Ni1 99.31(12) . . ? P1 N1 Ni1 129.17(10) . . ? C1 N2 C11 127.53(17) . . ? C1 N2 H2 112.6(18) . . ? C11 N2 H2 119.9(18) . . ? C2 O1 P1 120.96(12) . . ? C5 O2 P1 123.47(13) . . ? N2 C1 N1 124.45(17) . . ? N2 C1 S1 127.06(15) . . ? N1 C1 S1 108.49(14) . . ? N2 C1 Ni1 172.93(15) . . ? N1 C1 Ni1 48.60(9) . . ? S1 C1 Ni1 59.92(6) . . ? O1 C2 C3 108.23(17) . . ? O1 C2 C4 106.05(17) . . ? C3 C2 C4 114.3(2) . . ? O1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C4 C2 H2A 109.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C7 106.21(19) . . ? O2 C5 C6 110.29(18) . . ? C7 C5 C6 114.3(2) . . ? O2 C5 H5 108.6 . . ? C7 C5 H5 108.6 . . ? C6 C5 H5 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C16 C11 C12 121.20(19) . . ? C16 C11 N2 121.31(18) . . ? C12 C11 N2 117.42(17) . . ? C13 C12 C11 117.37(19) . . ? C13 C12 C17 120.7(2) . . ? C11 C12 C17 121.94(19) . . ? C14 C13 C12 122.0(2) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 119.7(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.0(2) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 S1 C1 1.12(8) . . . . ? N1 Ni1 S1 C1 -178.88(8) 2_667 . . . ? C1 Ni1 S1 C1 180.0 2_667 . . . ? O1 P1 N1 C1 114.82(19) . . . . ? O2 P1 N1 C1 -138.96(18) . . . . ? S2 P1 N1 C1 -12.0(2) . . . . ? O1 P1 N1 Ni1 -53.98(14) . . . . ? O2 P1 N1 Ni1 52.23(14) . . . . ? S2 P1 N1 Ni1 179.24(9) . . . . ? S1 Ni1 N1 C1 178.59(11) 2_667 . . . ? S1 Ni1 N1 C1 -1.41(11) . . . . ? C1 Ni1 N1 C1 179.999(2) 2_667 . . . ? S1 Ni1 N1 P1 -9.97(14) 2_667 . . . ? S1 Ni1 N1 P1 170.03(14) . . . . ? C1 Ni1 N1 P1 171.4(2) . . . . ? C1 Ni1 N1 P1 -8.6(2) 2_667 . . . ? O2 P1 O1 C2 71.57(15) . . . . ? N1 P1 O1 C2 -179.03(14) . . . . ? S2 P1 O1 C2 -51.31(15) . . . . ? O1 P1 O2 C5 -166.33(14) . . . . ? N1 P1 O2 C5 88.08(16) . . . . ? S2 P1 O2 C5 -41.49(15) . . . . ? C11 N2 C1 N1 -178.49(19) . . . . ? C11 N2 C1 S1 1.3(3) . . . . ? P1 N1 C1 N2 10.4(3) . . . . ? Ni1 N1 C1 N2 -178.36(17) . . . . ? P1 N1 C1 S1 -169.38(13) . . . . ? Ni1 N1 C1 S1 1.85(14) . . . . ? P1 N1 C1 Ni1 -171.2(2) . . . . ? Ni1 S1 C1 N2 178.61(19) . . . . ? Ni1 S1 C1 N1 -1.60(12) . . . . ? N1 Ni1 C1 N1 180.0 2_667 . . . ? S1 Ni1 C1 N1 -2.02(15) 2_667 . . . ? S1 Ni1 C1 N1 177.98(15) . . . . ? N1 Ni1 C1 S1 -177.98(15) . . . . ? N1 Ni1 C1 S1 2.02(15) 2_667 . . . ? S1 Ni1 C1 S1 180.0 2_667 . . . ? P1 O1 C2 C3 -99.46(19) . . . . ? P1 O1 C2 C4 137.43(17) . . . . ? P1 O2 C5 C7 164.32(17) . . . . ? P1 O2 C5 C6 -71.3(2) . . . . ? C1 N2 C11 C16 -44.4(3) . . . . ? C1 N2 C11 C12 138.6(2) . . . . ? C16 C11 C12 C13 1.4(3) . . . . ? N2 C11 C12 C13 178.49(18) . . . . ? C16 C11 C12 C17 -178.7(2) . . . . ? N2 C11 C12 C17 -1.6(3) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C17 C12 C13 C14 179.9(2) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C12 C11 C16 C15 -1.8(3) . . . . ? N2 C11 C16 C15 -178.76(18) . . . . ? C14 C15 C16 C11 1.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S2 0.896(10) 2.333(15) 3.1571(17) 153(2) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.905 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.085 data_safin39 _database_code_depnum_ccdc_archive 'CCDC 736209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H52 N4 Ni O4 P2 S4' _chemical_formula_sum 'C32 H52 N4 Ni O4 P2 S4' _chemical_formula_weight 805.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2223(5) _cell_length_b 10.4480(6) _cell_length_c 11.6919(7) _cell_angle_alpha 97.788(5) _cell_angle_beta 102.023(5) _cell_angle_gamma 111.808(4) _cell_volume 994.49(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14716 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.7 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8035 _exptl_absorpt_correction_T_max 0.8407 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15144 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 26.35 _reflns_number_total 4039 _reflns_number_gt 3691 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0434P)^2^+0.5370P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4039 _refine_ls_number_parameters 221 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.0000 0.01947(10) Uani 1 2 d S . . P1 P 0.73834(6) 0.41353(5) 0.19399(4) 0.02342(12) Uani 1 1 d . . . S1 S 0.82684(8) 0.44938(6) 0.36709(5) 0.03883(15) Uani 1 1 d . . . S2 S 0.53570(6) 0.69819(5) 0.12163(5) 0.02818(13) Uani 1 1 d . . . N1 N 0.6504(2) 0.51633(17) 0.14741(14) 0.0231(3) Uani 1 1 d . . . N2 N 0.7688(2) 0.71692(18) 0.31376(15) 0.0265(4) Uani 1 1 d D . . H2 H 0.822(3) 0.674(3) 0.352(2) 0.046(8) Uiso 1 1 d D . . O1 O 0.61080(17) 0.25601(14) 0.13371(13) 0.0254(3) Uani 1 1 d . A . O2 O 0.86497(18) 0.42986(15) 0.11937(14) 0.0302(3) Uani 1 1 d . . . C1 C 0.6661(2) 0.6425(2) 0.20652(17) 0.0226(4) Uani 1 1 d . . . C2 C 0.4947(3) 0.1716(2) 0.1915(2) 0.0346(5) Uani 1 1 d . . . H2A H 0.5496 0.2126 0.2795 0.042 Uiso 0.473(13) 1 calc PR A 1 H2B H 0.5199 0.2160 0.2786 0.042 Uiso 0.527(13) 1 calc PR A 2 C3 C 0.3558(8) 0.1981(8) 0.1723(8) 0.049(2) Uiso 0.473(13) 1 d P A 1 H3A H 0.3870 0.3005 0.1839 0.073 Uiso 0.473(13) 1 calc PR A 1 H3B H 0.2957 0.1627 0.2295 0.073 Uiso 0.473(13) 1 calc PR A 1 H3C H 0.2867 0.1500 0.0900 0.073 Uiso 0.473(13) 1 calc PR A 1 C3' C 0.3164(7) 0.1503(6) 0.1138(6) 0.0438(17) Uiso 0.527(13) 1 d P A 2 H3'1 H 0.3086 0.2420 0.1232 0.066 Uiso 0.527(13) 1 calc PR A 2 H3'2 H 0.2325 0.0845 0.1426 0.066 Uiso 0.527(13) 1 calc PR A 2 H3'3 H 0.3002 0.1116 0.0287 0.066 Uiso 0.527(13) 1 calc PR A 2 C4 C 0.4931(3) 0.0273(3) 0.1713(3) 0.0465(6) Uani 1 1 d . A . H4A H 0.6020 0.0337 0.2080 0.070 Uiso 1 1 calc R . . H4B H 0.4610 -0.0138 0.0847 0.070 Uiso 1 1 calc R . . H4C H 0.4151 -0.0329 0.2079 0.070 Uiso 1 1 calc R . . C5 C 0.9621(3) 0.3447(2) 0.1300(2) 0.0374(5) Uani 1 1 d . . . H5 H 0.9160 0.2695 0.1730 0.045 Uiso 1 1 calc R . . C6 C 1.1337(4) 0.4425(4) 0.2018(4) 0.0826(13) Uani 1 1 d . . . H6A H 1.1343 0.4832 0.2825 0.124 Uiso 1 1 calc R . . H6B H 1.1771 0.5189 0.1616 0.124 Uiso 1 1 calc R . . H6C H 1.2016 0.3891 0.2080 0.124 Uiso 1 1 calc R . . C7 C 0.9488(4) 0.2765(3) 0.0044(3) 0.0508(7) Uani 1 1 d . . . H7A H 0.8349 0.2133 -0.0370 0.076 Uiso 1 1 calc R . . H7B H 1.0150 0.2216 0.0076 0.076 Uiso 1 1 calc R . . H7C H 0.9878 0.3501 -0.0394 0.076 Uiso 1 1 calc R . . C11 C 0.7630(2) 0.8408(2) 0.37932(17) 0.0253(4) Uani 1 1 d . . . C12 C 0.8489(2) 0.9746(2) 0.36139(18) 0.0276(4) Uani 1 1 d . . . C13 C 0.8470(3) 1.0916(2) 0.43257(19) 0.0290(4) Uani 1 1 d . . . H13 H 0.9056 1.1835 0.4220 0.035 Uiso 1 1 calc R . . C14 C 0.7623(3) 1.0784(2) 0.51843(19) 0.0321(5) Uani 1 1 d . . . C15 C 0.6743(3) 0.9428(2) 0.5313(2) 0.0353(5) Uani 1 1 d . . . H15 H 0.6130 0.9323 0.5881 0.042 Uiso 1 1 calc R . . C16 C 0.6738(3) 0.8229(2) 0.46353(19) 0.0314(4) Uani 1 1 d . . . C17 C 0.9402(3) 0.9928(3) 0.2675(2) 0.0387(5) Uani 1 1 d . . . H17A H 0.8632 0.9675 0.1878 0.058 Uiso 1 1 calc R . . H17B H 0.9982 0.9309 0.2692 0.058 Uiso 1 1 calc R . . H17C H 1.0186 1.0917 0.2844 0.058 Uiso 1 1 calc R . . C18 C 0.7680(3) 1.2073(2) 0.5985(2) 0.0424(6) Uani 1 1 d . . . H18A H 0.8588 1.2389 0.6716 0.064 Uiso 1 1 calc R . . H18B H 0.6656 1.1831 0.6204 0.064 Uiso 1 1 calc R . . H18C H 0.7831 1.2835 0.5556 0.064 Uiso 1 1 calc R . . C19 C 0.5804(4) 0.6764(2) 0.4798(3) 0.0458(6) Uani 1 1 d . . . H19A H 0.5174 0.6828 0.5366 0.069 Uiso 1 1 calc R . . H19B H 0.6570 0.6364 0.5113 0.069 Uiso 1 1 calc R . . H19C H 0.5064 0.6151 0.4021 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02444(18) 0.01566(17) 0.02078(18) 0.00416(12) 0.00477(13) 0.01182(13) P1 0.0296(3) 0.0205(2) 0.0259(2) 0.00890(19) 0.00743(19) 0.0155(2) S1 0.0582(4) 0.0333(3) 0.0282(3) 0.0101(2) 0.0008(2) 0.0273(3) S2 0.0350(3) 0.0215(2) 0.0282(3) -0.00020(19) -0.0006(2) 0.0189(2) N1 0.0303(8) 0.0197(8) 0.0232(8) 0.0045(6) 0.0054(6) 0.0157(7) N2 0.0319(9) 0.0232(8) 0.0253(8) 0.0041(7) 0.0022(7) 0.0159(7) O1 0.0333(7) 0.0190(6) 0.0302(7) 0.0095(5) 0.0152(6) 0.0129(6) O2 0.0304(7) 0.0268(7) 0.0437(9) 0.0142(6) 0.0154(6) 0.0184(6) C1 0.0260(9) 0.0187(9) 0.0246(9) 0.0054(7) 0.0067(7) 0.0109(7) C2 0.0475(13) 0.0261(10) 0.0392(12) 0.0141(9) 0.0268(10) 0.0149(9) C4 0.0543(15) 0.0258(12) 0.0570(16) 0.0146(11) 0.0184(12) 0.0107(11) C5 0.0318(11) 0.0299(11) 0.0568(15) 0.0083(10) 0.0109(10) 0.0209(9) C6 0.0390(15) 0.067(2) 0.121(3) -0.030(2) -0.0112(17) 0.0348(15) C7 0.0499(15) 0.0387(14) 0.0677(18) 0.0015(12) 0.0231(13) 0.0228(12) C11 0.0301(10) 0.0202(9) 0.0225(9) 0.0010(7) 0.0011(7) 0.0119(8) C12 0.0271(9) 0.0248(10) 0.0277(10) 0.0067(8) 0.0012(8) 0.0104(8) C13 0.0314(10) 0.0187(9) 0.0316(10) 0.0054(8) 0.0025(8) 0.0080(8) C14 0.0399(11) 0.0222(10) 0.0288(10) 0.0015(8) 0.0026(9) 0.0124(9) C15 0.0490(13) 0.0267(11) 0.0307(11) 0.0049(9) 0.0154(10) 0.0145(10) C16 0.0412(12) 0.0208(10) 0.0282(10) 0.0037(8) 0.0082(9) 0.0100(9) C17 0.0398(12) 0.0350(12) 0.0464(13) 0.0152(10) 0.0178(10) 0.0158(10) C18 0.0599(15) 0.0235(11) 0.0400(13) -0.0001(9) 0.0118(11) 0.0168(11) C19 0.0638(16) 0.0241(11) 0.0529(15) 0.0109(10) 0.0301(13) 0.0138(11) _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 N1 1.9162(16) . ? Ni1 N1 1.9162(16) 2_665 ? Ni1 S2 2.2178(5) 2_665 ? Ni1 S2 2.2178(5) . ? Ni1 C1 2.4866(19) 2_665 ? Ni1 C1 2.4866(19) . ? P1 O2 1.5719(15) . ? P1 O1 1.5782(15) . ? P1 N1 1.6521(16) . ? P1 S1 1.9447(8) . ? S2 C1 1.7174(19) . ? N1 C1 1.344(2) . ? N2 C1 1.330(3) . ? N2 C11 1.437(2) . ? N2 H2 0.871(10) . ? O1 C2 1.464(2) . ? O2 C5 1.478(2) . ? C2 C3 1.389(7) . ? C2 C4 1.487(3) . ? C2 C3' 1.622(6) . ? C2 H2A 1.0000 . ? C2 H2B 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C3' H3'1 0.9800 . ? C3' H3'2 0.9800 . ? C3' H3'3 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.502(4) . ? C5 C6 1.506(4) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C11 C12 1.397(3) . ? C11 C16 1.398(3) . ? C12 C13 1.391(3) . ? C12 C17 1.508(3) . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 C15 1.393(3) . ? C14 C18 1.509(3) . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C19 1.513(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 179.999(2) . 2_665 ? N1 Ni1 S2 105.39(5) . 2_665 ? N1 Ni1 S2 74.61(5) 2_665 2_665 ? N1 Ni1 S2 74.61(5) . . ? N1 Ni1 S2 105.39(5) 2_665 . ? S2 Ni1 S2 180.0 2_665 . ? N1 Ni1 C1 147.64(6) . 2_665 ? N1 Ni1 C1 32.36(6) 2_665 2_665 ? S2 Ni1 C1 42.34(4) 2_665 2_665 ? S2 Ni1 C1 137.66(4) . 2_665 ? N1 Ni1 C1 32.36(6) . . ? N1 Ni1 C1 147.64(6) 2_665 . ? S2 Ni1 C1 137.66(4) 2_665 . ? S2 Ni1 C1 42.34(4) . . ? C1 Ni1 C1 180.0 2_665 . ? O2 P1 O1 100.96(8) . . ? O2 P1 N1 102.88(8) . . ? O1 P1 N1 106.21(8) . . ? O2 P1 S1 115.36(7) . . ? O1 P1 S1 113.77(6) . . ? N1 P1 S1 115.97(6) . . ? C1 S2 Ni1 77.22(7) . . ? C1 N1 P1 128.80(14) . . ? C1 N1 Ni1 97.88(12) . . ? P1 N1 Ni1 133.32(10) . . ? C1 N2 C11 122.97(16) . . ? C1 N2 H2 116(2) . . ? C11 N2 H2 119(2) . . ? C2 O1 P1 123.35(13) . . ? C5 O2 P1 119.38(14) . . ? N2 C1 N1 126.10(17) . . ? N2 C1 S2 123.85(15) . . ? N1 C1 S2 110.03(14) . . ? N2 C1 Ni1 173.66(15) . . ? N1 C1 Ni1 49.76(9) . . ? S2 C1 Ni1 60.44(6) . . ? C3 C2 O1 111.4(3) . . ? C3 C2 C4 124.2(4) . . ? O1 C2 C4 107.14(18) . . ? O1 C2 C3' 106.0(2) . . ? C4 C2 C3' 105.0(3) . . ? C3 C2 H2A 104.0 . . ? O1 C2 H2A 104.0 . . ? C4 C2 H2A 104.0 . . ? C3' C2 H2A 129.2 . . ? O1 C2 H2B 112.7 . . ? C4 C2 H2B 112.7 . . ? C3' C2 H2B 112.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C3' H3'1 109.5 . . ? C2 C3' H3'2 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? C2 C3' H3'3 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C7 107.0(2) . . ? O2 C5 C6 107.8(2) . . ? C7 C5 C6 113.5(3) . . ? O2 C5 H5 109.5 . . ? C7 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C16 121.74(19) . . ? C12 C11 N2 120.42(19) . . ? C16 C11 N2 117.80(18) . . ? C13 C12 C11 117.92(19) . . ? C13 C12 C17 120.59(19) . . ? C11 C12 C17 121.49(19) . . ? C14 C13 C12 122.01(19) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 118.4(2) . . ? C13 C14 C18 121.1(2) . . ? C15 C14 C18 120.5(2) . . ? C16 C15 C14 121.8(2) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C11 118.1(2) . . ? C15 C16 C19 121.4(2) . . ? C11 C16 C19 120.50(19) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 S2 C1 2.85(9) . . . . ? N1 Ni1 S2 C1 -177.15(9) 2_665 . . . ? C1 Ni1 S2 C1 180.0 2_665 . . . ? O2 P1 N1 C1 -108.05(18) . . . . ? O1 P1 N1 C1 146.31(17) . . . . ? S1 P1 N1 C1 18.8(2) . . . . ? O2 P1 N1 Ni1 71.89(15) . . . . ? O1 P1 N1 Ni1 -33.75(15) . . . . ? S1 P1 N1 Ni1 -161.23(10) . . . . ? S2 Ni1 N1 C1 176.42(11) 2_665 . . . ? S2 Ni1 N1 C1 -3.58(11) . . . . ? S2 Ni1 N1 P1 -3.54(14) 2_665 . . . ? S2 Ni1 N1 P1 176.46(14) . . . . ? O2 P1 O1 C2 160.44(16) . . . . ? N1 P1 O1 C2 -92.55(17) . . . . ? S1 P1 O1 C2 36.24(17) . . . . ? O1 P1 O2 C5 -66.23(16) . . . . ? N1 P1 O2 C5 -175.86(15) . . . . ? S1 P1 O2 C5 56.87(17) . . . . ? C11 N2 C1 N1 -170.74(19) . . . . ? C11 N2 C1 S2 10.8(3) . . . . ? P1 N1 C1 N2 6.1(3) . . . . ? Ni1 N1 C1 N2 -173.88(18) . . . . ? P1 N1 C1 S2 -175.29(11) . . . . ? Ni1 N1 C1 S2 4.75(14) . . . . ? P1 N1 C1 Ni1 180.0(2) . . . . ? Ni1 S2 C1 N2 174.50(18) . . . . ? Ni1 S2 C1 N1 -4.17(13) . . . . ? P1 O1 C2 C3 84.6(4) . . . . ? P1 O1 C2 C4 -136.54(18) . . . . ? P1 O1 C2 C3' 111.7(3) . . . . ? P1 O2 C5 C7 130.54(18) . . . . ? P1 O2 C5 C6 -107.1(3) . . . . ? C1 N2 C11 C12 -88.4(3) . . . . ? C1 N2 C11 C16 93.7(2) . . . . ? C16 C11 C12 C13 1.7(3) . . . . ? N2 C11 C12 C13 -176.11(18) . . . . ? C16 C11 C12 C17 -177.9(2) . . . . ? N2 C11 C12 C17 4.3(3) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C17 C12 C13 C14 179.0(2) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C12 C13 C14 C18 177.3(2) . . . . ? C13 C14 C15 C16 2.0(4) . . . . ? C18 C14 C15 C16 -176.5(2) . . . . ? C14 C15 C16 C11 -0.9(4) . . . . ? C14 C15 C16 C19 178.8(2) . . . . ? C12 C11 C16 C15 -1.0(3) . . . . ? N2 C11 C16 C15 176.9(2) . . . . ? C12 C11 C16 C19 179.3(2) . . . . ? N2 C11 C16 C19 -2.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.871(10) 2.399(19) 3.1520(18) 145(3) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.571 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.061 data_safin31 _database_code_depnum_ccdc_archive 'CCDC 736210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 N4 Ni O4 P2 S4' _chemical_formula_sum 'C16 H36 N4 Ni O4 P2 S4' _chemical_formula_weight 597.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7500(17) _cell_length_b 8.8100(18) _cell_length_c 9.6200(19) _cell_angle_alpha 93.60(3) _cell_angle_beta 90.68(3) _cell_angle_gamma 111.40(3) _cell_volume 688.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6369 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour grey _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 _exptl_absorpt_coefficient_mu 1.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7386 _exptl_absorpt_correction_T_max 0.7775 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7919 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.65 _reflns_number_total 2564 _reflns_number_gt 2242 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.1011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2564 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 1.0000 0.5000 1.0000 0.01863(13) Uani 1 2 d S . . P1 P 0.73775(7) 0.44828(6) 0.73892(5) 0.01894(14) Uani 1 1 d . . . S1 S 0.92473(7) 0.38006(6) 0.78809(5) 0.02364(15) Uani 1 1 d . . . S2 S 0.98882(7) 0.74196(6) 0.96219(5) 0.02546(15) Uani 1 1 d . . . N1 N 0.7835(2) 0.6394(2) 0.72495(18) 0.0228(4) Uani 1 1 d . . . N2 N 0.9049(3) 0.9100(2) 0.7839(2) 0.0307(5) Uani 1 1 d . . . H2 H 0.962(4) 0.992(4) 0.844(3) 0.045(8) Uiso 1 1 d . . . O1 O 0.65845(18) 0.35652(17) 0.59601(14) 0.0217(3) Uani 1 1 d . . . O2 O 0.59339(18) 0.39222(17) 0.84055(14) 0.0231(3) Uani 1 1 d . . . C1 C 0.8817(3) 0.7565(2) 0.8114(2) 0.0222(4) Uani 1 1 d . . . C2 C 0.8243(4) 0.9472(3) 0.6650(3) 0.0443(7) Uani 1 1 d . . . H2A H 0.8597 0.9070 0.5787 0.067 Uiso 1 1 calc R . . H2B H 0.8537 1.0657 0.6652 0.067 Uiso 1 1 calc R . . H2C H 0.7049 0.8940 0.6708 0.067 Uiso 1 1 calc R . . C3 C 0.7466(3) 0.3976(3) 0.4655(2) 0.0236(4) Uani 1 1 d . . . H3 H 0.8613 0.4758 0.4879 0.028 Uiso 1 1 calc R . . C4 C 0.6576(3) 0.4782(3) 0.3793(2) 0.0347(5) Uani 1 1 d . . . H4A H 0.6596 0.5790 0.4299 0.052 Uiso 1 1 calc R . . H4B H 0.5435 0.4039 0.3613 0.052 Uiso 1 1 calc R . . H4C H 0.7117 0.5043 0.2906 0.052 Uiso 1 1 calc R . . C5 C 0.7518(4) 0.2418(3) 0.3970(3) 0.0441(7) Uani 1 1 d . . . H5A H 0.8118 0.1964 0.4585 0.066 Uiso 1 1 calc R . . H5B H 0.8075 0.2643 0.3086 0.066 Uiso 1 1 calc R . . H5C H 0.6395 0.1630 0.3792 0.066 Uiso 1 1 calc R . . C6 C 0.5138(3) 0.2220(3) 0.8781(2) 0.0281(5) Uani 1 1 d . . . H6 H 0.5796 0.1559 0.8445 0.034 Uiso 1 1 calc R . . C7 C 0.3454(3) 0.1543(3) 0.8083(3) 0.0447(7) Uani 1 1 d . . . H7A H 0.3555 0.1515 0.7069 0.067 Uiso 1 1 calc R . . H7B H 0.2842 0.2240 0.8365 0.067 Uiso 1 1 calc R . . H7C H 0.2869 0.0433 0.8361 0.067 Uiso 1 1 calc R . . C8 C 0.5122(4) 0.2303(3) 1.0349(3) 0.0464(7) Uani 1 1 d . . . H8A H 0.6253 0.2758 1.0733 0.070 Uiso 1 1 calc R . . H8B H 0.4572 0.1202 1.0659 0.070 Uiso 1 1 calc R . . H8C H 0.4531 0.3005 1.0675 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0205(2) 0.01907(19) 0.0171(2) -0.00060(13) -0.00208(14) 0.00855(15) P1 0.0216(3) 0.0176(2) 0.0170(3) 0.00079(19) -0.0010(2) 0.0065(2) S1 0.0287(3) 0.0254(3) 0.0200(3) -0.0032(2) -0.0039(2) 0.0146(2) S2 0.0335(3) 0.0199(2) 0.0232(3) -0.0017(2) -0.0071(2) 0.0108(2) N1 0.0247(10) 0.0193(8) 0.0237(9) 0.0029(7) -0.0040(7) 0.0070(7) N2 0.0415(12) 0.0189(9) 0.0287(10) 0.0015(8) -0.0091(9) 0.0079(8) O1 0.0229(8) 0.0237(7) 0.0161(7) -0.0001(5) -0.0011(6) 0.0059(6) O2 0.0263(8) 0.0197(7) 0.0231(7) 0.0016(6) 0.0053(6) 0.0081(6) C1 0.0243(11) 0.0222(10) 0.0209(10) 0.0029(8) 0.0024(8) 0.0093(9) C2 0.071(2) 0.0230(11) 0.0374(14) 0.0053(10) -0.0193(13) 0.0150(12) C3 0.0241(12) 0.0333(11) 0.0162(10) 0.0045(8) 0.0036(8) 0.0133(9) C4 0.0382(14) 0.0471(14) 0.0262(11) 0.0093(10) 0.0039(10) 0.0234(12) C5 0.067(2) 0.0473(15) 0.0304(13) 0.0018(11) 0.0099(12) 0.0360(14) C6 0.0367(13) 0.0188(10) 0.0288(12) 0.0068(8) 0.0113(10) 0.0090(9) C7 0.0378(16) 0.0306(13) 0.0535(17) 0.0025(11) 0.0052(12) -0.0018(11) C8 0.062(2) 0.0499(16) 0.0317(14) 0.0162(12) 0.0159(13) 0.0238(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.2126(9) 2_767 ? Ni1 S1 2.2126(9) . ? Ni1 S2 2.2213(7) 2_767 ? Ni1 S2 2.2214(7) . ? P1 O2 1.5589(16) . ? P1 O1 1.5663(15) . ? P1 N1 1.5977(17) . ? P1 S1 1.9992(9) . ? S2 C1 1.754(2) . ? N1 C1 1.313(3) . ? N2 C1 1.336(3) . ? N2 C2 1.453(3) . ? N2 H2 0.88(3) . ? O1 C3 1.477(2) . ? O2 C6 1.475(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C5 1.501(3) . ? C3 C4 1.503(3) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.504(4) . ? C6 C8 1.506(3) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 S1 Ni1 S1 179.999(12) 2_767 . ? S1 Ni1 S2 98.52(3) 2_767 2_767 ? S1 Ni1 S2 81.48(3) . 2_767 ? S1 Ni1 S2 81.48(3) 2_767 . ? S1 Ni1 S2 98.52(3) . . ? S2 Ni1 S2 180.0 2_767 . ? O2 P1 O1 103.54(8) . . ? O2 P1 N1 107.15(9) . . ? O1 P1 N1 107.83(9) . . ? O2 P1 S1 113.64(6) . . ? O1 P1 S1 107.98(7) . . ? N1 P1 S1 115.87(8) . . ? P1 S1 Ni1 102.04(4) . . ? C1 S2 Ni1 117.81(8) . . ? C1 N1 P1 125.20(15) . . ? C1 N2 C2 122.07(19) . . ? C1 N2 H2 119.6(19) . . ? C2 N2 H2 118.0(19) . . ? C3 O1 P1 120.90(13) . . ? C6 O2 P1 123.64(13) . . ? N1 C1 N2 116.96(19) . . ? N1 C1 S2 129.21(16) . . ? N2 C1 S2 113.83(16) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C5 107.30(18) . . ? O1 C3 C4 107.58(17) . . ? C5 C3 C4 113.9(2) . . ? O1 C3 H3 109.3 . . ? C5 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 C7 107.62(18) . . ? O2 C6 C8 105.89(19) . . ? C7 C6 C8 113.8(2) . . ? O2 C6 H6 109.8 . . ? C7 C6 H6 109.8 . . ? C8 C6 H6 109.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 S1 Ni1 -59.79(7) . . . . ? O1 P1 S1 Ni1 -174.04(6) . . . . ? N1 P1 S1 Ni1 64.96(8) . . . . ? S2 Ni1 S1 P1 136.47(4) 2_767 . . . ? S2 Ni1 S1 P1 -43.53(4) . . . . ? S1 Ni1 S2 C1 -163.90(8) 2_767 . . . ? S1 Ni1 S2 C1 16.10(8) . . . . ? O2 P1 N1 C1 84.2(2) . . . . ? O1 P1 N1 C1 -164.91(18) . . . . ? S1 P1 N1 C1 -43.8(2) . . . . ? O2 P1 O1 C3 169.46(14) . . . . ? N1 P1 O1 C3 56.14(16) . . . . ? S1 P1 O1 C3 -69.76(14) . . . . ? O1 P1 O2 C6 64.89(17) . . . . ? N1 P1 O2 C6 178.70(16) . . . . ? S1 P1 O2 C6 -51.98(17) . . . . ? P1 N1 C1 N2 -179.51(16) . . . . ? P1 N1 C1 S2 0.0(3) . . . . ? C2 N2 C1 N1 0.8(3) . . . . ? C2 N2 C1 S2 -178.8(2) . . . . ? Ni1 S2 C1 N1 11.6(2) . . . . ? Ni1 S2 C1 N2 -168.87(14) . . . . ? P1 O1 C3 C5 126.07(18) . . . . ? P1 O1 C3 C4 -110.99(18) . . . . ? P1 O2 C6 C7 -108.4(2) . . . . ? P1 O2 C6 C8 129.52(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S2 0.88(3) 2.80(3) 3.628(2) 156(3) 2_777 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.399 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.063