# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 loop_ _publ_author_name _publ_author_address D.Safin ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; M.Babashkina ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; A.Klein ;Kazan State University Kremlevskaya str.18, 420008, Kazan Russian Federation ; F.Sokolov ;Kazan State University Kremlevskaya str.18, 420008, Kazan Russian Federation ; S.Baranov ;Kazan State University Kremlevskaya str.18, 420008, Kazan Russian Federation ; T.Pape '' ; E.Hahn ; '' D.Krivolapov '' _publ_contact_author_name 'Safin, Damir' _publ_contact_author_email damir.safin@ksu.ru _publ_section_title ; The influence of the intramolecular hydrogen bond on the 1,3-N,S-coordination of crown ether-containing N-phosphorylthiourea with NiII ; _publ_contact_author_address ;Institute of Organic & Physical Chemistry Arbuzov Str.8 420088 Kazan Russia ; _publ_contact_author_fax ;+7(843)2732253 ; _publ_contact_author_phone ;+7(843)2727573 ; # Attachment 'HLI.cif' data_s7 _database_code_depnum_ccdc_archive 'CCDC 732320' # start Validation Reply Form _vrf_PLAT242_s7 ; PROBLEM: Low Ueq as Compared to Neighbors for C24 RESPONSE: This is an atom of a terminal isopropyl group showing increased thermal motion. However, no split model could be found. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic "N-diisopropoxyphosphinyl-N'-(benzo-15-crown-5)-4'-yl-thiourea " _chemical_name_common N-diisopropoxyphosphinyl-N'-(benzo-15-crown-5)-4'-yl-thiourea _chemical_formula_moiety 'C21 H35 N2 O8 P S' _chemical_formula_sum 'C21 H35 N2 O8 P S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 506.54 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 'C c' _symmetry_int_tables_number 9 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 31.721(19) _cell_length_b 8.715(5) _cell_length_c 9.919(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.486(7) _cell_angle_gamma 90.00 _cell_volume 2629(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2747 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 24.21 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9557 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type SmartApex2 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7658 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4826 _reflns_number_gt 3430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.23(12) _refine_ls_number_reflns 4826 _refine_ls_number_parameters 296 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_restrained_S_all 1.231 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.77065(15) 0.3360(5) 0.4143(4) 0.0663(10) Uani 1 1 d . . . C2 C 0.72479(16) 0.2375(5) 0.5629(5) 0.0695(11) Uani 1 1 d . . . C3 C 0.70891(16) 0.3007(5) 0.6658(5) 0.0721(11) Uani 1 1 d . . . H3 H 0.7214 0.3903 0.7105 0.087 Uiso 1 1 calc R . . C4 C 0.67484(16) 0.2333(5) 0.7036(5) 0.0737(11) Uani 1 1 d . . . C6 C 0.6631(2) 0.4432(8) 0.8449(8) 0.117(2) Uani 1 1 d . . . H6A H 0.6634 0.5078 0.7655 0.140 Uiso 1 1 calc R . . H6B H 0.6915 0.4519 0.9146 0.140 Uiso 1 1 calc R . . C7 C 0.6289(3) 0.4931(11) 0.9044(10) 0.137(3) Uani 1 1 d . A . H7A H 0.6285 0.4245 0.9810 0.164 Uiso 1 1 calc R . . H7B H 0.6365 0.5945 0.9442 0.164 Uiso 1 1 calc R . . C10 C 0.5187(5) 0.448(2) 0.8271(19) 0.212(6) Uani 1 1 d D . . H101 H 0.5000 0.4842 0.8826 0.254 Uiso 0.600(9) 1 calc PR A 1 H102 H 0.5079 0.4987 0.7367 0.254 Uiso 0.600(9) 1 calc PR A 1 H103 H 0.4974 0.5293 0.8216 0.254 Uiso 0.400(9) 1 d PR A 2 H104 H 0.5143 0.3780 0.8977 0.254 Uiso 0.400(9) 1 d PR A 2 C9 C 0.5547(5) 0.5132(17) 0.882(2) 0.224(8) Uani 1 1 d . A . H9A H 0.5659 0.4747 0.9773 0.269 Uiso 1 1 calc R . . H9B H 0.5489 0.6217 0.8888 0.269 Uiso 1 1 calc R . . O11 O 0.5072(6) 0.3116(18) 0.8011(17) 0.177(4) Uani 0.600(9) 1 d PD A 1 C13 C 0.5364(5) 0.131(2) 0.693(2) 0.194(5) Uani 0.600(9) 1 d PD A 1 H13A H 0.5596 0.1909 0.6726 0.233 Uiso 0.600(9) 1 calc PR A 1 H13B H 0.5472 0.0954 0.7893 0.233 Uiso 0.600(9) 1 calc PR A 1 C12 C 0.4963(5) 0.237(3) 0.681(2) 0.194(5) Uani 0.600(9) 1 d PD A 1 H124 H 0.4921 0.3073 0.6023 0.233 Uiso 0.600(9) 1 calc PR A 1 H123 H 0.4697 0.1781 0.6700 0.233 Uiso 0.600(9) 1 calc PR A 1 O11A O 0.5073(7) 0.384(3) 0.703(2) 0.177(4) Uani 0.400(9) 1 d PD A 2 C12A C 0.5269(10) 0.251(3) 0.703(4) 0.194(5) Uani 0.400(9) 1 d PD A 2 H121 H 0.5492 0.2466 0.7925 0.233 Uiso 0.400(9) 1 calc PR A 2 H122 H 0.5426 0.2614 0.6323 0.233 Uiso 0.400(9) 1 calc PR A 2 C13A C 0.5065(9) 0.088(3) 0.680(4) 0.194(5) Uani 0.400(9) 1 d PD A 2 H13C H 0.5090 0.0394 0.7702 0.233 Uiso 0.400(9) 1 calc PR A 2 H13D H 0.4756 0.0937 0.6283 0.233 Uiso 0.400(9) 1 calc PR A 2 C15 C 0.5590(4) -0.1030(12) 0.6628(16) 0.188(5) Uani 1 1 d . A . H15A H 0.5458 -0.2024 0.6338 0.226 Uiso 1 1 calc R . . H15B H 0.5673 -0.0991 0.7647 0.226 Uiso 1 1 calc R . . C16 C 0.5993(3) -0.0866(9) 0.6145(10) 0.139(3) Uani 1 1 d . . . H16A H 0.6173 -0.1781 0.6379 0.167 Uiso 1 1 calc R . . H16B H 0.5912 -0.0725 0.5134 0.167 Uiso 1 1 calc R . . C18 C 0.65661(17) 0.0992(6) 0.6366(6) 0.0805(13) Uani 1 1 d . . . C19 C 0.6727(2) 0.0363(6) 0.5350(7) 0.0942(16) Uani 1 1 d . . . H19 H 0.6605 -0.0539 0.4906 0.113 Uiso 1 1 calc R . . C20 C 0.7070(2) 0.1056(6) 0.4976(6) 0.0930(15) Uani 1 1 d . . . H20 H 0.7178 0.0624 0.4283 0.112 Uiso 1 1 calc R . . C21 C 0.9030(3) 0.2896(9) 0.5992(9) 0.1236(16) Uani 1 1 d . . . H21 H 0.8764 0.2267 0.5825 0.148 Uiso 1 1 calc R . . C22 C 0.9305(4) 0.2313(15) 0.5050(14) 0.188(5) Uani 1 1 d . . . H22A H 0.9134 0.2367 0.4083 0.282 Uiso 1 1 calc R . . H22B H 0.9391 0.1268 0.5288 0.282 Uiso 1 1 calc R . . H22C H 0.9563 0.2937 0.5189 0.282 Uiso 1 1 calc R . . C23 C 0.9273(3) 0.2852(15) 0.7551(10) 0.177(5) Uani 1 1 d . . . H23A H 0.9083 0.3215 0.8083 0.266 Uiso 1 1 calc R . . H23B H 0.9529 0.3496 0.7732 0.266 Uiso 1 1 calc R . . H23C H 0.9362 0.1817 0.7824 0.266 Uiso 1 1 calc R . . C24 C 0.8259(3) 0.7960(8) 0.5223(10) 0.1236(16) Uani 1 1 d . . . H24 H 0.7974 0.7495 0.5183 0.148 Uiso 1 1 calc R . . C25 C 0.8179(5) 0.8835(14) 0.3834(14) 0.218(7) Uani 1 1 d . . . H25A H 0.8128 0.8118 0.3071 0.327 Uiso 1 1 calc R . . H25B H 0.8431 0.9451 0.3857 0.327 Uiso 1 1 calc R . . H25C H 0.7926 0.9485 0.3704 0.327 Uiso 1 1 calc R . . C26 C 0.8341(6) 0.8850(15) 0.6284(15) 0.228(7) Uani 1 1 d . . . H26A H 0.8372 0.8256 0.7122 0.343 Uiso 1 1 calc R . . H26B H 0.8103 0.9567 0.6175 0.343 Uiso 1 1 calc R . . H26C H 0.8609 0.9399 0.6356 0.343 Uiso 1 1 calc R . . N1 N 0.80779(14) 0.4233(5) 0.4219(4) 0.0711(9) Uani 1 1 d . . . H1 H 0.8126 0.4386 0.3419 0.085 Uiso 1 1 calc R . . N2 N 0.76140(13) 0.3164(4) 0.5337(4) 0.0729(10) Uani 1 1 d . . . H2 H 0.7799 0.3565 0.6058 0.087 Uiso 1 1 calc R . . O1 O 0.83186(12) 0.4836(4) 0.6847(3) 0.0785(9) Uani 1 1 d . . . O2 O 0.89061(13) 0.4425(5) 0.5589(4) 0.1000(11) Uani 1 1 d . . . O3 O 0.85408(15) 0.6675(4) 0.5142(4) 0.1027(12) Uani 1 1 d . . . O5 O 0.65552(15) 0.2882(5) 0.8002(5) 0.1065(13) Uani 1 1 d . . . O8 O 0.5887(2) 0.4988(9) 0.8164(9) 0.178(3) Uani 1 1 d . . . O14 O 0.5284(3) 0.0107(14) 0.6092(12) 0.207(4) Uani 1 1 d D . . O17 O 0.62253(14) 0.0403(5) 0.6818(5) 0.1043(12) Uani 1 1 d . . . P1 P 0.84442(7) 0.50325(14) 0.5552(2) 0.0707(3) Uani 1 1 d . . . S1 S 0.74168(7) 0.27163(15) 0.2563(2) 0.0880(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.080(3) 0.065(3) 0.056(2) 0.0067(18) 0.0228(19) 0.017(2) C2 0.083(3) 0.067(3) 0.057(2) 0.0063(19) 0.017(2) 0.003(2) C3 0.089(3) 0.076(3) 0.055(2) -0.0006(19) 0.027(2) -0.013(2) C4 0.083(3) 0.070(3) 0.074(3) -0.001(2) 0.032(2) -0.013(2) C6 0.124(5) 0.134(5) 0.118(5) -0.055(4) 0.076(4) -0.067(4) C7 0.124(6) 0.152(7) 0.139(7) -0.051(5) 0.045(5) -0.009(5) C10 0.155(11) 0.28(2) 0.240(17) -0.009(14) 0.118(12) 0.024(12) C9 0.199(13) 0.216(13) 0.33(2) -0.043(13) 0.193(16) -0.007(10) O11 0.205(9) 0.165(10) 0.195(12) -0.008(8) 0.109(9) 0.005(8) C13 0.124(8) 0.240(17) 0.232(11) -0.038(14) 0.073(9) -0.005(11) C12 0.124(8) 0.240(17) 0.232(11) -0.038(14) 0.073(9) -0.005(11) O11A 0.205(9) 0.165(10) 0.195(12) -0.008(8) 0.109(9) 0.005(8) C12A 0.124(8) 0.240(17) 0.232(11) -0.038(14) 0.073(9) -0.005(11) C13A 0.124(8) 0.240(17) 0.232(11) -0.038(14) 0.073(9) -0.005(11) C15 0.186(10) 0.148(8) 0.262(14) -0.058(9) 0.114(11) -0.102(8) C16 0.152(6) 0.104(5) 0.164(7) -0.020(5) 0.049(5) -0.058(5) C18 0.088(3) 0.068(3) 0.088(3) 0.002(2) 0.030(3) -0.012(2) C19 0.122(4) 0.064(3) 0.101(4) -0.012(3) 0.040(3) -0.011(3) C20 0.113(4) 0.080(3) 0.098(4) -0.012(3) 0.050(3) -0.002(3) C21 0.139(4) 0.099(3) 0.153(5) -0.005(3) 0.076(4) 0.000(3) C22 0.155(8) 0.219(12) 0.203(12) -0.063(9) 0.070(8) 0.036(7) C23 0.151(7) 0.255(13) 0.116(7) 0.052(7) 0.020(5) 0.073(8) C24 0.139(4) 0.099(3) 0.153(5) -0.005(3) 0.076(4) 0.000(3) C25 0.258(14) 0.147(8) 0.188(12) 0.013(7) -0.037(10) 0.020(8) C26 0.314(17) 0.184(11) 0.208(12) -0.075(10) 0.109(12) -0.076(12) N1 0.089(2) 0.089(3) 0.0424(16) 0.0071(16) 0.0301(16) 0.0063(19) N2 0.083(2) 0.092(3) 0.0479(17) -0.0020(17) 0.0261(17) -0.0004(19) O1 0.089(2) 0.108(3) 0.0448(14) -0.0006(13) 0.0291(14) 0.0014(16) O2 0.095(2) 0.125(3) 0.091(2) -0.004(2) 0.044(2) 0.000(2) O3 0.139(3) 0.097(3) 0.087(2) 0.003(2) 0.056(2) -0.016(2) O5 0.128(3) 0.107(3) 0.112(3) -0.037(2) 0.078(3) -0.050(2) O8 0.120(4) 0.227(8) 0.194(7) -0.081(5) 0.058(5) -0.026(4) O14 0.138(5) 0.240(9) 0.234(10) -0.063(8) 0.039(6) -0.029(5) O17 0.110(3) 0.098(3) 0.108(3) -0.010(2) 0.038(2) -0.038(2) P1 0.0827(7) 0.0877(7) 0.0513(5) 0.0053(5) 0.0345(5) 0.0095(6) S1 0.1094(9) 0.0955(9) 0.0576(6) -0.0090(6) 0.0213(6) 0.0025(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.310(5) . ? C1 N1 1.387(6) . ? C1 S1 1.673(5) . ? C2 C20 1.361(7) . ? C2 C3 1.375(7) . ? C2 N2 1.447(6) . ? C3 C4 1.372(6) . ? C4 O5 1.363(6) . ? C4 C18 1.387(7) . ? C6 O5 1.421(7) . ? C6 C7 1.442(10) . ? C7 O8 1.325(10) . ? C10 O11 1.249(15) . ? C10 C9 1.254(17) . ? C10 O11A 1.309(16) . ? C9 O8 1.415(12) . ? O11 C12 1.314(15) . ? C13 O14 1.317(14) . ? C13 C12 1.550(2) . ? O11A C12A 1.311(16) . ? C12A C13A 1.550(2) . ? C13A O14 1.312(16) . ? C15 O14 1.383(15) . ? C15 C16 1.494(13) . ? C16 O17 1.390(8) . ? C18 C19 1.368(8) . ? C18 O17 1.381(6) . ? C19 C20 1.383(9) . ? C21 O2 1.414(8) . ? C21 C23 1.520(13) . ? C21 C22 1.536(12) . ? C24 C26 1.274(13) . ? C24 O3 1.450(8) . ? C24 C25 1.531(16) . ? N1 P1 1.647(4) . ? O1 P1 1.459(3) . ? O2 P1 1.549(4) . ? O3 P1 1.542(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 115.3(4) . . ? N2 C1 S1 126.8(4) . . ? N1 C1 S1 117.9(3) . . ? C20 C2 C3 120.1(5) . . ? C20 C2 N2 123.7(4) . . ? C3 C2 N2 116.2(4) . . ? C4 C3 C2 121.0(4) . . ? O5 C4 C3 126.0(4) . . ? O5 C4 C18 115.0(4) . . ? C3 C4 C18 118.9(5) . . ? O5 C6 C7 109.5(5) . . ? O8 C7 C6 115.9(7) . . ? O11 C10 C9 134.1(18) . . ? O11 C10 O11A 54.0(12) . . ? C9 C10 O11A 125.2(17) . . ? C10 C9 O8 118.7(14) . . ? C10 O11 C12 130.0(17) . . ? O14 C13 C12 114.9(16) . . ? O11 C12 C13 103.1(16) . . ? C10 O11A C12A 112(2) . . ? O11A C12A C13A 129(3) . . ? O14 C13A C12A 106.6(19) . . ? O14 C15 C16 112.2(10) . . ? O17 C16 C15 107.9(7) . . ? C19 C18 O17 125.5(5) . . ? C19 C18 C4 119.9(5) . . ? O17 C18 C4 114.6(5) . . ? C18 C19 C20 120.6(5) . . ? C2 C20 C19 119.6(5) . . ? O2 C21 C23 109.4(7) . . ? O2 C21 C22 107.5(8) . . ? C23 C21 C22 113.5(8) . . ? C26 C24 O3 122.1(12) . . ? C26 C24 C25 112.5(10) . . ? O3 C24 C25 106.4(8) . . ? C1 N1 P1 132.1(3) . . ? C1 N2 C2 129.8(4) . . ? C21 O2 P1 121.0(4) . . ? C24 O3 P1 122.0(4) . . ? C4 O5 C6 118.9(4) . . ? C7 O8 C9 114.6(11) . . ? C13A O14 C13 44.4(12) . . ? C13A O14 C15 126(2) . . ? C13 O14 C15 109.9(13) . . ? C18 O17 C16 119.8(6) . . ? O1 P1 O3 117.7(2) . . ? O1 P1 O2 115.6(2) . . ? O3 P1 O2 93.8(3) . . ? O1 P1 N1 110.5(2) . . ? O3 P1 N1 109.2(2) . . ? O2 P1 N1 108.8(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.351 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.048 # Attachment '[NiLI2].cif' data_z100 _database_code_depnum_ccdc_archive 'CCDC 732346' # start Validation Reply Form _vrf_PLAT220_z100 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.34 Ratio RESPONSE: This is an atom of a terminal isopropyl group showing increased thermal motion. However, no split model could be found. ; _vrf_PLAT222_z100 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.52 Ratio RESPONSE: This is an atom of a terminal isopropyl group showing increased thermal motion. However, no split model could be found. ; _vrf_PLAT770_z100 ; PROBLEM: Suspect C-H Bond in CIF: C27 -- H25A .. 1.40 Ang. RESPONSE: the isopropyl group is disordered and the short contact between C27 and H25 in part1 and part2 ; _audit_creation_method SHELXL-97 _chemical_name_systematic Bis[N-diisopropoxy-N'-(benzo-15-crown-5-4'-yl)-thiocarbamido-N,S]nickel _chemical_name_common ;Bis(N-diisopropoxy-N'-(benzo-15-crown-5-4'-yl)-thiocarbamido- N,S)nickel ; _chemical_formula_moiety 'C42 H68 N4 Ni O16 P2 S2' _chemical_formula_sum 'C42 H68 N4 Ni O16 P2 S2' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour green _diffrn_ambient_temperature 293(2) _chemical_formula_weight 1069.77 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.4922(15) _cell_length_b 15.482(3) _cell_length_c 32.203(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.214(13) _cell_angle_gamma 90.00 _cell_volume 5222.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1554 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 23.98 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2264 _exptl_absorpt_coefficient_mu 0.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8010 _exptl_absorpt_correction_T_max 0.8928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type SmartApex2 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5562 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0799 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.29 _reflns_number_total 5266 _reflns_number_gt 3106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+4.6368P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5266 _refine_ls_number_parameters 304 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C3 C 0.1688(3) 0.0529(2) 0.34559(10) 0.0330(8) Uani 1 1 d . . . C4 C 0.2134(3) 0.1195(2) 0.37129(10) 0.0332(8) Uani 1 1 d . . . H4 H 0.2448 0.1697 0.3597 0.040 Uiso 1 1 calc R . . C5 C 0.2115(3) 0.1115(2) 0.41392(10) 0.0320(8) Uani 1 1 d . . . C6 C 0.1611(3) 0.0372(2) 0.43129(10) 0.0338(8) Uani 1 1 d . . . C7 C 0.1128(4) -0.0270(3) 0.40475(12) 0.0462(10) Uani 1 1 d . . . H7 H 0.0767 -0.0762 0.4158 0.055 Uiso 1 1 calc R . . C8 C 0.1175(4) -0.0191(3) 0.36217(11) 0.0445(10) Uani 1 1 d . . . H8 H 0.0857 -0.0630 0.3448 0.053 Uiso 1 1 calc R . . C10 C 0.1635(4) -0.0504(2) 0.49215(12) 0.0497(10) Uani 1 1 d . . . H102 H 0.2206 -0.0885 0.4781 0.060 Uiso 1 1 calc R . . H101 H 0.0783 -0.0748 0.4897 0.060 Uiso 1 1 calc R . . C11 C 0.2066(4) -0.0419(3) 0.53705(12) 0.0538(11) Uani 1 1 d . . . H111 H 0.1509 -0.0027 0.5510 0.065 Uiso 1 1 calc R . . H112 H 0.2040 -0.0978 0.5507 0.065 Uiso 1 1 calc R . . C1 C 0.2942(3) 0.0647(2) 0.28541(10) 0.0329(8) Uani 1 1 d . A . C13 C 0.3845(5) 0.0021(3) 0.58032(13) 0.0740(15) Uani 1 1 d . . . H131 H 0.3949 -0.0532 0.5942 0.089 Uiso 1 1 calc R . . H132 H 0.3281 0.0376 0.5960 0.089 Uiso 1 1 calc R . . C14 C 0.5110(5) 0.0454(3) 0.57802(16) 0.0779(16) Uani 1 1 d . . . H142 H 0.5565 0.0414 0.6050 0.093 Uiso 1 1 calc R . . H141 H 0.5604 0.0146 0.5582 0.093 Uiso 1 1 calc R . . C16 C 0.4792(4) 0.1471(3) 0.52273(13) 0.0592(12) Uani 1 1 d . . . H161 H 0.3883 0.1447 0.5155 0.071 Uiso 1 1 calc R . . H162 H 0.5216 0.1035 0.5069 0.071 Uiso 1 1 calc R . . C17 C 0.5303(5) 0.2344(3) 0.51380(14) 0.0666(13) Uani 1 1 d . . . H171 H 0.4900 0.2770 0.5309 0.080 Uiso 1 1 calc R . . H172 H 0.6214 0.2356 0.5208 0.080 Uiso 1 1 calc R . . C19 C 0.3868(4) 0.2934(3) 0.46047(12) 0.0530(11) Uani 1 1 d . . . H193 H 0.3988 0.3532 0.4525 0.064 Uiso 1 1 calc R . . H191 H 0.3356 0.2928 0.4846 0.064 Uiso 1 1 calc R . . C20 C 0.3173(4) 0.2462(3) 0.42545(11) 0.0494(10) Uani 1 1 d . . . H201 H 0.2516 0.2829 0.4125 0.059 Uiso 1 1 calc R . . H202 H 0.3763 0.2304 0.4046 0.059 Uiso 1 1 calc R . . C22 C 0.2698(5) -0.1185(3) 0.20873(15) 0.0683(13) Uani 1 1 d . . . H22 H 0.2804 -0.1053 0.2385 0.082 Uiso 1 1 calc R . . C23 C 0.1474(6) -0.1697(4) 0.2000(2) 0.112(2) Uani 1 1 d . . . H233 H 0.0762 -0.1371 0.2091 0.168 Uiso 1 1 calc R . . H231 H 0.1530 -0.2236 0.2148 0.168 Uiso 1 1 calc R . . H232 H 0.1356 -0.1806 0.1707 0.168 Uiso 1 1 calc R . . C24 C 0.3857(6) -0.1672(4) 0.1952(2) 0.109(2) Uani 1 1 d . . . H241 H 0.4611 -0.1335 0.2016 0.164 Uiso 1 1 calc R . . H243 H 0.3770 -0.1777 0.1658 0.164 Uiso 1 1 calc R . . H242 H 0.3924 -0.2214 0.2097 0.164 Uiso 1 1 calc R . . C25 C 0.2045(6) 0.1964(3) 0.16690(16) 0.0822(15) Uani 1 1 d D . . H25 H 0.1761 0.2205 0.1930 0.099 Uiso 0.391(11) 1 calc PR A 1 H25A H 0.1171 0.1956 0.1762 0.099 Uiso 0.609(11) 1 d PR A 2 C26 C 0.3175(12) 0.2384(12) 0.1505(7) 0.153(5) Uani 0.391(11) 1 d PD A 1 H262 H 0.3833 0.2434 0.1723 0.229 Uiso 0.391(11) 1 calc PR A 1 H261 H 0.2946 0.2949 0.1403 0.229 Uiso 0.391(11) 1 calc PR A 1 H263 H 0.3481 0.2043 0.1283 0.229 Uiso 0.391(11) 1 calc PR A 1 C27 C 0.1056(18) 0.1917(13) 0.1325(6) 0.153(5) Uani 0.391(11) 1 d PD A 1 H272 H 0.0368 0.1556 0.1406 0.229 Uiso 0.391(11) 1 calc PR A 1 H273 H 0.1419 0.1677 0.1084 0.229 Uiso 0.391(11) 1 calc PR A 1 H271 H 0.0739 0.2486 0.1263 0.229 Uiso 0.391(11) 1 calc PR A 1 C27A C 0.1477(17) 0.2178(8) 0.1252(3) 0.1529(5) Uani 0.609(11) 1 d PD A 2 H27D H 0.1051 0.1678 0.1135 0.229 Uiso 0.609(11) 1 calc PR A 2 H27E H 0.2137 0.2356 0.1076 0.229 Uiso 0.609(11) 1 calc PR A 2 H27F H 0.0872 0.2638 0.1275 0.229 Uiso 0.609(11) 1 calc PR A 2 C26A C 0.2908(15) 0.2601(7) 0.1877(5) 0.153(5) Uani 0.609(11) 1 d PD A 2 H26D H 0.3039 0.2454 0.2166 0.229 Uiso 0.609(11) 1 calc PR A 2 H26E H 0.2535 0.3166 0.1852 0.229 Uiso 0.609(11) 1 calc PR A 2 H26F H 0.3713 0.2597 0.1750 0.229 Uiso 0.609(11) 1 calc PR A 2 N1 N 0.3184(2) 0.0669(2) 0.24518(8) 0.0346(7) Uani 1 1 d . A . N2 N 0.1821(2) 0.0594(2) 0.30168(8) 0.0363(7) Uani 1 1 d . . . H2 H 0.1144 0.0599 0.2853 0.044 Uiso 1 1 calc R . . O1 O 0.0858(2) 0.0492(2) 0.21728(8) 0.0669(10) Uani 1 1 d . A . O2 O 0.2619(3) -0.03920(18) 0.18514(7) 0.0491(7) Uani 1 1 d . A . O3 O 0.2518(2) 0.10844(18) 0.16963(7) 0.0469(7) Uani 1 1 d . A . O9 O 0.1636(2) 0.03315(16) 0.47355(7) 0.0424(6) Uani 1 1 d . . . O12 O 0.3312(3) -0.0101(2) 0.53911(8) 0.0573(8) Uani 1 1 d . . . O15 O 0.5036(3) 0.1332(2) 0.56622(9) 0.0785(10) Uani 1 1 d . . . O18 O 0.5067(3) 0.2556(2) 0.47090(9) 0.0617(8) Uani 1 1 d . . . O21 O 0.2612(2) 0.17046(16) 0.44188(7) 0.0426(6) Uani 1 1 d . . . P1 P 0.21711(8) 0.04698(7) 0.20517(3) 0.0386(3) Uani 1 1 d . . . S2 S 0.43894(8) 0.06852(7) 0.31440(3) 0.0442(3) Uani 1 1 d . A . Ni1 Ni 0.5000 0.06753(4) 0.2500 0.0328(2) Uani 1 2 d S . . 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 C3 0.0183(15) 0.052(2) 0.0288(17) -0.0037(16) 0.0006(13) 0.0010(15) C4 0.0319(18) 0.040(2) 0.0281(17) 0.0024(16) 0.0042(14) 0.0021(16) C5 0.0264(17) 0.038(2) 0.0317(18) -0.0039(16) 0.0003(14) -0.0029(15) C6 0.0298(17) 0.041(2) 0.0308(18) -0.0017(16) 0.0015(14) -0.0049(16) C7 0.046(2) 0.048(2) 0.045(2) -0.0044(19) 0.0065(17) -0.0188(19) C8 0.043(2) 0.053(3) 0.038(2) -0.0115(18) -0.0009(16) -0.0148(19) C10 0.053(2) 0.046(3) 0.049(2) 0.0075(19) -0.0045(18) -0.017(2) C11 0.061(3) 0.054(3) 0.047(2) 0.016(2) 0.001(2) -0.011(2) C1 0.0255(16) 0.044(2) 0.0282(17) -0.0048(15) -0.0030(13) 0.0045(15) C13 0.091(4) 0.083(4) 0.045(3) 0.017(2) -0.018(2) -0.017(3) C14 0.083(4) 0.079(4) 0.068(3) 0.014(3) -0.040(3) -0.017(3) C16 0.058(3) 0.061(3) 0.057(3) -0.005(2) -0.007(2) -0.008(2) C17 0.060(3) 0.067(3) 0.071(3) -0.004(2) -0.012(2) -0.021(2) C19 0.068(3) 0.043(2) 0.048(2) -0.0015(19) 0.004(2) -0.021(2) C20 0.072(3) 0.041(2) 0.036(2) 0.0038(17) 0.0005(18) -0.020(2) C22 0.085(4) 0.057(3) 0.061(3) 0.000(2) -0.012(2) -0.008(3) C23 0.101(5) 0.090(5) 0.145(6) 0.010(4) 0.003(4) -0.034(4) C24 0.091(5) 0.080(4) 0.154(6) -0.009(4) -0.016(4) 0.016(3) C25 0.107(4) 0.065(4) 0.074(3) 0.002(3) -0.003(3) 0.007(3) C26 0.177(10) 0.066(6) 0.206(13) 0.009(7) -0.084(10) -0.024(6) C27 0.177(10) 0.066(6) 0.206(13) 0.009(7) -0.084(10) -0.024(6) C27A 0.1767(17) 0.0659(8) 0.2056(3) 0.0094(15) -0.0838(7) -0.0241(5) C26A 0.177(10) 0.066(6) 0.206(13) 0.009(7) -0.084(10) -0.024(6) N1 0.0195(13) 0.057(2) 0.0271(14) -0.0013(14) -0.0015(11) 0.0005(13) N2 0.0192(13) 0.063(2) 0.0263(14) -0.0066(14) -0.0046(11) 0.0009(13) O1 0.0220(12) 0.142(3) 0.0362(14) -0.0110(17) -0.0029(10) -0.0042(16) O2 0.0556(16) 0.0551(18) 0.0359(14) -0.0073(13) -0.0043(12) -0.0072(14) O3 0.0430(14) 0.0610(19) 0.0363(14) 0.0065(12) -0.0037(11) 0.0127(13) O9 0.0606(17) 0.0361(14) 0.0306(13) 0.0035(11) 0.0055(11) -0.0127(13) O12 0.0593(18) 0.070(2) 0.0414(15) 0.0021(14) -0.0073(13) -0.0138(16) O15 0.107(3) 0.067(2) 0.0570(19) 0.0025(16) -0.0321(18) -0.0180(19) O18 0.0544(18) 0.075(2) 0.0562(18) 0.0004(16) 0.0063(14) -0.0132(16) O21 0.0611(16) 0.0393(15) 0.0274(12) -0.0040(11) 0.0033(11) -0.0192(13) P1 0.0223(4) 0.0691(7) 0.0240(4) -0.0037(4) -0.0037(3) -0.0010(4) S2 0.0216(4) 0.0844(8) 0.0261(4) -0.0028(5) -0.0042(3) 0.0012(5) Ni1 0.0175(3) 0.0556(5) 0.0250(3) 0.000 -0.0030(2) 0.000 _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 C3 C8 1.361(5) . ? C3 C4 1.386(5) . ? C3 N2 1.432(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 O21 1.364(4) . ? C5 C6 1.397(5) . ? C6 O9 1.361(4) . ? C6 C7 1.389(5) . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 O9 1.426(4) . ? C10 C11 1.497(5) . ? C10 H102 0.9700 . ? C10 H101 0.9700 . ? C11 O12 1.395(5) . ? C11 H111 0.9700 . ? C11 H112 0.9700 . ? C1 N2 1.316(4) . ? C1 N1 1.335(4) . ? C1 S2 1.739(3) . ? C1 Ni1 2.499(3) . ? C13 O12 1.424(5) . ? C13 C14 1.493(7) . ? C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 O15 1.411(6) . ? C14 H142 0.9700 . ? C14 H141 0.9700 . ? C16 O15 1.426(5) . ? C16 C17 1.487(6) . ? C16 H161 0.9700 . ? C16 H162 0.9700 . ? C17 O18 1.428(5) . ? C17 H171 0.9700 . ? C17 H172 0.9700 . ? C19 O18 1.411(5) . ? C19 C20 1.499(5) . ? C19 H193 0.9700 . ? C19 H191 0.9700 . ? C20 O21 1.427(4) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C22 O2 1.444(5) . ? C22 C24 1.515(7) . ? C22 C23 1.522(7) . ? C22 H22 0.9800 . ? C23 H233 0.9600 . ? C23 H231 0.9600 . ? C23 H232 0.9600 . ? C24 H241 0.9600 . ? C24 H243 0.9600 . ? C24 H242 0.9600 . ? C25 O3 1.449(6) . ? C25 C26A 1.475(6) . ? C25 C27A 1.475(6) . ? C25 C27 1.476(6) . ? C25 C26 1.476(6) . ? C25 H25 0.9800 . ? C25 H25A 0.9800 . ? C26 H262 0.9600 . ? C26 H261 0.9600 . ? C26 H263 0.9600 . ? C27 H25A 1.4047 . ? C27 H272 0.9600 . ? C27 H273 0.9600 . ? C27 H271 0.9600 . ? C27A H27D 0.9600 . ? C27A H27E 0.9600 . ? C27A H27F 0.9600 . ? C26A H26D 0.9600 . ? C26A H26E 0.9600 . ? C26A H26F 0.9600 . ? N1 P1 1.652(3) . ? N1 Ni1 1.903(2) . ? N2 H2 0.8600 . ? O1 P1 1.453(3) . ? O2 P1 1.566(3) . ? O3 P1 1.548(3) . ? S2 Ni1 2.2048(9) . ? Ni1 N1 1.903(2) 2_655 ? Ni1 S2 2.2048(9) 2_655 ? Ni1 C1 2.499(3) 2_655 ? 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 C8 C3 C4 120.2(3) . . ? C8 C3 N2 120.5(3) . . ? C4 C3 N2 119.3(3) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.8 . . ? O21 C5 C4 124.8(3) . . ? O21 C5 C6 115.2(3) . . ? C4 C5 C6 119.9(3) . . ? O9 C6 C7 124.6(3) . . ? O9 C6 C5 116.9(3) . . ? C7 C6 C5 118.5(3) . . ? C8 C7 C6 121.0(4) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C3 C8 C7 120.0(3) . . ? C3 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? O9 C10 C11 108.6(3) . . ? O9 C10 H102 110.0 . . ? C11 C10 H102 110.0 . . ? O9 C10 H101 110.0 . . ? C11 C10 H101 110.0 . . ? H102 C10 H101 108.3 . . ? O12 C11 C10 108.0(3) . . ? O12 C11 H111 110.1 . . ? C10 C11 H111 110.1 . . ? O12 C11 H112 110.1 . . ? C10 C11 H112 110.1 . . ? H111 C11 H112 108.4 . . ? N2 C1 N1 127.6(3) . . ? N2 C1 S2 124.2(2) . . ? N1 C1 S2 108.2(2) . . ? N2 C1 Ni1 175.6(2) . . ? N1 C1 Ni1 48.71(15) . . ? S2 C1 Ni1 59.54(10) . . ? O12 C13 C14 108.5(4) . . ? O12 C13 H131 110.0 . . ? C14 C13 H131 110.0 . . ? O12 C13 H132 110.0 . . ? C14 C13 H132 110.0 . . ? H131 C13 H132 108.4 . . ? O15 C14 C13 114.2(4) . . ? O15 C14 H142 108.7 . . ? C13 C14 H142 108.7 . . ? O15 C14 H141 108.7 . . ? C13 C14 H141 108.7 . . ? H142 C14 H141 107.6 . . ? O15 C16 C17 106.3(3) . . ? O15 C16 H161 110.5 . . ? C17 C16 H161 110.5 . . ? O15 C16 H162 110.5 . . ? C17 C16 H162 110.5 . . ? H161 C16 H162 108.7 . . ? O18 C17 C16 110.6(3) . . ? O18 C17 H171 109.5 . . ? C16 C17 H171 109.5 . . ? O18 C17 H172 109.5 . . ? C16 C17 H172 109.5 . . ? H171 C17 H172 108.1 . . ? O18 C19 C20 111.5(4) . . ? O18 C19 H193 109.3 . . ? C20 C19 H193 109.3 . . ? O18 C19 H191 109.3 . . ? C20 C19 H191 109.3 . . ? H193 C19 H191 108.0 . . ? O21 C20 C19 108.4(3) . . ? O21 C20 H201 110.0 . . ? C19 C20 H201 110.0 . . ? O21 C20 H202 110.0 . . ? C19 C20 H202 110.0 . . ? H201 C20 H202 108.4 . . ? O2 C22 C24 107.2(4) . . ? O2 C22 C23 108.8(4) . . ? C24 C22 C23 111.8(5) . . ? O2 C22 H22 109.7 . . ? C24 C22 H22 109.7 . . ? C23 C22 H22 109.7 . . ? C22 C23 H233 109.5 . . ? C22 C23 H231 109.5 . . ? H233 C23 H231 109.5 . . ? C22 C23 H232 109.5 . . ? H233 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C22 C24 H241 109.5 . . ? C22 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? C22 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? H243 C24 H242 109.5 . . ? O3 C25 C26A 113.7(7) . . ? O3 C25 C27A 112.7(7) . . ? C26A C25 C27A 118.0(8) . . ? O3 C25 C27 102.9(9) . . ? C26A C25 C27 139.6(9) . . ? C27A C25 C27 25.5(9) . . ? O3 C25 C26 99.0(9) . . ? C26A C25 C26 51.9(9) . . ? C27A C25 C26 82.4(10) . . ? C27 C25 C26 107.4(10) . . ? O3 C25 H25 114.9 . . ? C26A C25 H25 64.6 . . ? C27A C25 H25 124.5 . . ? C27 C25 H25 115.0 . . ? C26 C25 H25 115.7 . . ? O3 C25 H25A 107.1 . . ? C26A C25 H25A 115.5 . . ? C27A C25 H25A 86.7 . . ? C27 C25 H25A 66.3 . . ? C26 C25 H25A 153.9 . . ? H25 C25 H25A 53.4 . . ? C25 C26 H262 109.1 . . ? C25 C26 H261 109.1 . . ? H262 C26 H261 109.5 . . ? C25 C26 H263 110.3 . . ? H262 C26 H263 109.5 . . ? H261 C26 H263 109.5 . . ? C25 C27 H25A 39.7 . . ? C25 C27 H272 109.7 . . ? H25A C27 H272 77.4 . . ? C25 C27 H273 109.6 . . ? H25A C27 H273 144.5 . . ? H272 C27 H273 109.5 . . ? C25 C27 H271 109.1 . . ? H25A C27 H271 100.0 . . ? H272 C27 H271 109.5 . . ? H273 C27 H271 109.5 . . ? C25 C27A H27D 109.7 . . ? C25 C27A H27E 109.3 . . ? H27D C27A H27E 109.5 . . ? C25 C27A H27F 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? C25 C26A H26D 108.8 . . ? C25 C26A H26E 109.3 . . ? H26D C26A H26E 109.5 . . ? C25 C26A H26F 110.2 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C1 N1 P1 127.1(2) . . ? C1 N1 Ni1 99.51(19) . . ? P1 N1 Ni1 131.41(15) . . ? C1 N2 C3 122.4(3) . . ? C1 N2 H2 118.8 . . ? C3 N2 H2 118.8 . . ? C22 O2 P1 121.2(3) . . ? C25 O3 P1 121.9(3) . . ? C6 O9 C10 117.5(3) . . ? C11 O12 C13 114.2(3) . . ? C14 O15 C16 114.5(3) . . ? C19 O18 C17 115.5(3) . . ? C5 O21 C20 117.1(3) . . ? O1 P1 O3 116.73(17) . . ? O1 P1 O2 116.22(18) . . ? O3 P1 O2 97.51(14) . . ? O1 P1 N1 111.35(14) . . ? O3 P1 N1 107.13(15) . . ? O2 P1 N1 106.59(14) . . ? C1 S2 Ni1 77.64(11) . . ? N1 Ni1 N1 179.41(19) . 2_655 ? N1 Ni1 S2 74.59(8) . . ? N1 Ni1 S2 105.41(8) 2_655 . ? N1 Ni1 S2 105.41(8) . 2_655 ? N1 Ni1 S2 74.59(8) 2_655 2_655 ? S2 Ni1 S2 179.20(7) . 2_655 ? N1 Ni1 C1 148.19(11) . 2_655 ? N1 Ni1 C1 31.79(11) 2_655 2_655 ? S2 Ni1 C1 137.19(7) . 2_655 ? S2 Ni1 C1 42.83(7) 2_655 2_655 ? N1 Ni1 C1 31.79(11) . . ? N1 Ni1 C1 148.19(11) 2_655 . ? S2 Ni1 C1 42.83(7) . . ? S2 Ni1 C1 137.19(7) 2_655 . ? C1 Ni1 C1 177.98(17) 2_655 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.677 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.069 # Attachment '- [Ni(bipy)LII2]_Revised.cif' data_sad _database_code_depnum_ccdc_archive 'CCDC 735416' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 N6 Ni O6 P2 S2' _chemical_formula_weight 845.57 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 33.048(7) _cell_length_b 27.265(5) _cell_length_c 9.0412(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8146(3) _cell_formula_units_Z 8 _cell_measurement_temperature 153(1) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description stick _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3552 _exptl_absorpt_coefficient_mu 0.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8831 _exptl_absorpt_correction_T_max 0.9655 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.837053 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19710 _diffrn_reflns_av_R_equivalents 0.0974 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4666 _reflns_number_gt 3853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _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^)+(0.0135P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(11) _refine_ls_number_reflns 4666 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _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 0.2500 0.2500 0.90938(4) 0.01961(11) Uani 1 2 d S . . P1 P 0.18518(2) 0.34855(2) 0.88878(7) 0.02289(15) Uani 1 1 d . . . S1 S 0.28989(2) 0.29688(2) 1.09084(7) 0.02570(15) Uani 1 1 d . . . O3 O 0.14761(5) 0.31487(6) 0.92165(18) 0.0259(4) Uani 1 1 d . . . O1 O 0.18143(5) 0.39972(6) 0.94120(19) 0.0307(4) Uani 1 1 d . . . N1 N 0.22517(6) 0.31981(7) 0.9507(2) 0.0195(4) Uani 1 1 d . . . O2 O 0.18469(5) 0.34400(6) 0.71472(17) 0.0288(4) Uani 1 1 d . . . C1 C 0.25269(7) 0.33768(9) 1.0470(3) 0.0217(5) Uani 1 1 d . . . N2 N 0.24915(6) 0.38362(7) 1.1000(2) 0.0265(5) Uani 1 1 d . . . H2 H 0.2280 0.3994 1.0647 0.032 Uiso 1 1 calc R . . C2 C 0.27231(8) 0.41183(9) 1.2007(3) 0.0248(6) Uani 1 1 d . . . C3 C 0.25752(9) 0.45882(9) 1.2263(3) 0.0354(7) Uani 1 1 d . . . H3 H 0.2338 0.4697 1.1769 0.043 Uiso 1 1 calc R . . C7 C 0.30679(9) 0.39692(10) 1.2714(3) 0.0358(7) Uani 1 1 d . . . H7 H 0.3174 0.3651 1.2538 0.043 Uiso 1 1 calc R . . C18 C 0.11337(10) 0.34741(10) 1.1400(4) 0.0538(9) Uani 1 1 d . . . H18A H 0.1315 0.3758 1.1394 0.081 Uiso 1 1 calc R . . H18B H 0.1054 0.3400 1.2419 0.081 Uiso 1 1 calc R . . H18C H 0.0892 0.3547 1.0811 0.081 Uiso 1 1 calc R . . C6 C 0.32639(8) 0.42855(11) 1.3693(3) 0.0400(7) Uani 1 1 d . . . H6 H 0.3502 0.4178 1.4184 0.048 Uiso 1 1 calc R . . C13 C 0.19844(9) 0.38513(9) 0.6234(3) 0.0348(7) Uani 1 1 d . . . H13 H 0.1861 0.4161 0.6617 0.042 Uiso 1 1 calc R . . C5 C 0.31201(9) 0.47460(10) 1.3958(3) 0.0392(7) Uani 1 1 d . . . H5 H 0.3256 0.4959 1.4626 0.047 Uiso 1 1 calc R . . C17 C 0.10791(10) 0.26016(10) 1.0661(3) 0.0455(8) Uani 1 1 d . . . H17A H 0.0848 0.2674 1.0015 0.068 Uiso 1 1 calc R . . H17B H 0.0981 0.2518 1.1652 0.068 Uiso 1 1 calc R . . H17C H 0.1232 0.2325 1.0256 0.068 Uiso 1 1 calc R . . C4 C 0.27730(10) 0.48968(10) 1.3235(3) 0.0427(8) Uani 1 1 d . . . H4 H 0.2669 0.5217 1.3409 0.051 Uiso 1 1 calc R . . C15 C 0.24385(8) 0.38971(10) 0.6281(3) 0.0397(7) Uani 1 1 d . . . H15A H 0.2526 0.3946 0.7306 0.060 Uiso 1 1 calc R . . H15B H 0.2523 0.4178 0.5680 0.060 Uiso 1 1 calc R . . H15C H 0.2561 0.3597 0.5888 0.060 Uiso 1 1 calc R . . C16 C 0.13474(8) 0.30417(10) 1.0752(3) 0.0322(6) Uani 1 1 d . . . H16 H 0.1590 0.2962 1.1367 0.039 Uiso 1 1 calc R . . C14 C 0.18244(10) 0.37531(13) 0.4701(3) 0.0565(10) Uani 1 1 d . . . H14A H 0.1937 0.3444 0.4332 0.085 Uiso 1 1 calc R . . H14B H 0.1904 0.4021 0.4041 0.085 Uiso 1 1 calc R . . H14C H 0.1529 0.3730 0.4734 0.085 Uiso 1 1 calc R . . N3 N 0.28668(6) 0.26919(7) 0.7323(2) 0.0210(5) Uani 1 1 d . . . C11 C 0.34769(8) 0.29504(9) 0.6146(3) 0.0324(7) Uani 1 1 d . . . H11 H 0.3743 0.3080 0.6233 0.039 Uiso 1 1 calc R . . C12 C 0.32417(8) 0.28722(9) 0.7382(3) 0.0265(6) Uani 1 1 d . . . H12 H 0.3352 0.2951 0.8323 0.032 Uiso 1 1 calc R . . C8 C 0.27080(7) 0.25919(8) 0.5975(2) 0.0220(5) Uani 1 1 d . . . C9 C 0.29331(8) 0.26545(10) 0.4687(3) 0.0317(6) Uani 1 1 d . . . H9 H 0.2821 0.2571 0.3753 0.038 Uiso 1 1 calc R . . C10 C 0.33170(9) 0.28367(10) 0.4780(3) 0.0372(7) Uani 1 1 d . . . H10 H 0.3473 0.2885 0.3910 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 Ni1 0.0228(2) 0.0203(2) 0.0157(2) 0.000 0.000 0.0006(2) P1 0.0224(3) 0.0229(3) 0.0235(4) 0.0016(3) -0.0043(3) -0.0001(3) S1 0.0297(4) 0.0265(3) 0.0209(3) -0.0023(3) -0.0071(3) 0.0070(3) O3 0.0238(9) 0.0303(9) 0.0236(9) -0.0001(8) 0.0007(8) -0.0042(8) O1 0.0284(10) 0.0260(9) 0.0377(11) 0.0004(8) -0.0083(9) 0.0043(8) N1 0.0218(11) 0.0203(10) 0.0163(10) 0.0007(8) -0.0022(9) 0.0019(9) O2 0.0337(11) 0.0306(10) 0.0219(9) 0.0060(8) -0.0031(8) -0.0047(8) C1 0.0231(14) 0.0249(13) 0.0171(12) 0.0001(10) 0.0053(11) -0.0020(11) N2 0.0258(12) 0.0218(11) 0.0319(12) -0.0027(10) -0.0074(10) 0.0069(9) C2 0.0247(14) 0.0282(14) 0.0214(13) -0.0019(11) -0.0002(11) -0.0043(12) C3 0.0457(18) 0.0242(14) 0.0365(16) -0.0005(12) -0.0098(14) 0.0003(14) C7 0.0312(16) 0.0377(16) 0.0384(16) -0.0114(14) -0.0037(13) 0.0052(14) C18 0.064(2) 0.0493(18) 0.048(2) -0.0053(16) 0.0229(18) -0.0049(17) C6 0.0251(15) 0.061(2) 0.0341(17) -0.0146(15) -0.0089(13) -0.0012(14) C13 0.0369(16) 0.0312(15) 0.0361(18) 0.0115(13) 0.0003(13) 0.0012(13) C5 0.0436(18) 0.0418(17) 0.0323(15) -0.0065(14) 0.0015(15) -0.0186(15) C17 0.045(2) 0.0433(17) 0.0478(19) -0.0005(15) 0.0178(16) -0.0094(15) C4 0.064(2) 0.0267(15) 0.0376(17) -0.0049(13) -0.0084(17) -0.0061(15) C15 0.0368(17) 0.0372(16) 0.0452(19) 0.0067(14) 0.0083(15) -0.0033(13) C16 0.0273(15) 0.0413(16) 0.0278(14) 0.0093(12) 0.0008(12) -0.0013(13) C14 0.058(2) 0.076(2) 0.0355(18) 0.0233(17) -0.0127(17) -0.014(2) N3 0.0216(12) 0.0211(11) 0.0202(11) 0.0021(9) -0.0010(9) -0.0010(9) C11 0.0233(14) 0.0367(15) 0.0370(17) 0.0078(13) 0.0001(13) -0.0061(12) C12 0.0284(15) 0.0267(14) 0.0244(14) 0.0010(11) -0.0057(11) -0.0025(12) C8 0.0219(13) 0.0252(13) 0.0189(12) 0.0042(10) -0.0010(10) -0.0017(11) C9 0.0355(17) 0.0429(16) 0.0167(13) 0.0029(12) 0.0028(12) -0.0082(14) C10 0.0321(17) 0.0491(18) 0.0305(16) 0.0106(14) 0.0111(13) -0.0077(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 N3 2.0750(19) 14 ? Ni1 N3 2.075(2) . ? Ni1 N1 2.1062(18) . ? Ni1 N1 2.1062(18) 14 ? Ni1 S1 2.4624(7) . ? Ni1 S1 2.4624(7) 14 ? P1 O1 1.4787(17) . ? P1 O3 1.5726(17) . ? P1 O2 1.5787(17) . ? P1 N1 1.635(2) . ? S1 C1 1.705(3) . ? O3 C16 1.481(3) . ? N1 C1 1.350(3) . ? O2 C13 1.465(3) . ? C1 N2 1.346(3) . ? N2 C2 1.416(3) . ? C2 C7 1.368(4) . ? C2 C3 1.391(3) . ? C3 C4 1.381(4) . ? C7 C6 1.395(4) . ? C18 C16 1.494(4) . ? C6 C5 1.364(4) . ? C13 C15 1.507(4) . ? C13 C14 1.507(4) . ? C5 C4 1.383(4) . ? C17 C16 1.494(4) . ? N3 C12 1.334(3) . ? N3 C8 1.355(3) . ? C11 C12 1.377(3) . ? C11 C10 1.378(4) . ? C8 C9 1.392(3) . ? C8 C8 1.464(5) 14 ? C9 C10 1.365(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ni1 N3 79.05(11) 14 . ? N3 Ni1 N1 97.89(7) 14 . ? N3 Ni1 N1 97.86(7) . . ? N3 Ni1 N1 97.86(7) 14 14 ? N3 Ni1 N1 97.89(7) . 14 ? N1 Ni1 N1 159.54(10) . 14 ? N3 Ni1 S1 163.27(5) 14 . ? N3 Ni1 S1 94.03(6) . . ? N1 Ni1 S1 67.74(5) . . ? N1 Ni1 S1 98.17(5) 14 . ? N3 Ni1 S1 94.03(6) 14 14 ? N3 Ni1 S1 163.27(5) . 14 ? N1 Ni1 S1 98.17(5) . 14 ? N1 Ni1 S1 67.74(5) 14 14 ? S1 Ni1 S1 96.44(4) . 14 ? O1 P1 O3 115.11(10) . . ? O1 P1 O2 113.13(10) . . ? O3 P1 O2 97.72(9) . . ? O1 P1 N1 114.21(10) . . ? O3 P1 N1 107.05(10) . . ? O2 P1 N1 108.18(10) . . ? C1 S1 Ni1 78.32(9) . . ? C16 O3 P1 121.26(15) . . ? C1 N1 P1 126.33(16) . . ? C1 N1 Ni1 100.26(14) . . ? P1 N1 Ni1 133.40(11) . . ? C13 O2 P1 119.89(15) . . ? N2 C1 N1 120.4(2) . . ? N2 C1 S1 125.95(19) . . ? N1 C1 S1 113.60(17) . . ? C1 N2 C2 133.4(2) . . ? C7 C2 C3 119.2(2) . . ? C7 C2 N2 126.1(2) . . ? C3 C2 N2 114.7(2) . . ? C4 C3 C2 120.1(3) . . ? C2 C7 C6 119.9(3) . . ? C5 C6 C7 121.3(3) . . ? O2 C13 C15 110.9(2) . . ? O2 C13 C14 105.9(2) . . ? C15 C13 C14 113.0(3) . . ? C6 C5 C4 118.7(3) . . ? C3 C4 C5 120.8(3) . . ? O3 C16 C18 110.4(2) . . ? O3 C16 C17 106.1(2) . . ? C18 C16 C17 112.0(2) . . ? C12 N3 C8 118.0(2) . . ? C12 N3 Ni1 127.24(16) . . ? C8 N3 Ni1 114.65(15) . . ? C12 C11 C10 118.4(2) . . ? N3 C12 C11 123.3(2) . . ? N3 C8 C9 121.4(2) . . ? N3 C8 C8 115.64(13) . 14 ? C9 C8 C8 122.95(15) . 14 ? C10 C9 C8 119.3(2) . . ? C9 C10 C11 119.6(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.674 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.052