# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_safin229 #TrackingRef 'web_deposit_cif_file_0_DamirSafin_1344110069.safin229.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N O4 P' _chemical_formula_weight 309.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' 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 14.327(2) _cell_length_b 17.039(3) _cell_length_c 6.4900(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1584.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3921 _cell_measurement_theta_min 1.8534 _cell_measurement_theta_max 21.9154 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_T_min 0.65737 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; The crystal showed twinning one major domain and at least one minor domains which were NOT taken into account during integration, resulting in the high Rint value. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '90 images, \D\F 2.25\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8565 _diffrn_reflns_av_R_equivalents 0.1340 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 21.96 _reflns_number_total 1926 _reflns_number_gt 1744 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0189P)^2^+8.6934P] 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(15) _refine_ls_number_reflns 1926 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.1706 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.80273(5) 0.47870(4) -0.04366(16) 0.0336(2) Uani 1 1 d . . . O2 O 0.79011(16) 0.45101(11) -0.2584(3) 0.0395(7) Uani 1 1 d . . . O3 O 0.89631(14) 0.48745(11) 0.0388(3) 0.0359(6) Uani 1 1 d . . . O4 O 0.75156(15) 0.42073(11) 0.1205(3) 0.0356(6) Uani 1 1 d . . . C5 C 0.65623(10) 0.41315(7) 0.1416(2) 0.0276(9) Uani 1 1 d G . . C6 C 0.59459(12) 0.40926(12) -0.0234(3) 0.0419(10) Uani 1 1 d G . . H6 H 0.6175 0.4125 -0.1606 0.050 Uiso 1 1 calc R . . C7 C 0.49948(11) 0.40058(13) 0.0121(4) 0.0466(11) Uani 1 1 d G . . H7 H 0.4574 0.3979 -0.1007 0.056 Uiso 1 1 calc R . . C8 C 0.46600(10) 0.39579(13) 0.2127(4) 0.0488(11) Uani 1 1 d G . . H8 H 0.4010 0.3899 0.2370 0.059 Uiso 1 1 calc R . . C9 C 0.52763(13) 0.39968(15) 0.3778(3) 0.0543(12) Uani 1 1 d G . . H9 H 0.5047 0.3964 0.5149 0.065 Uiso 1 1 calc R . . C10 C 0.62275(12) 0.40836(12) 0.3423(2) 0.0446(11) Uani 1 1 d G . . H10 H 0.6649 0.4110 0.4551 0.054 Uiso 1 1 calc R . . O11 O 0.74474(14) 0.55990(10) -0.0290(3) 0.0354(6) Uani 1 1 d . . . C12 C 0.75052(9) 0.61275(8) 0.1323(2) 0.0326(9) Uani 1 1 d G . . C13 C 0.74645(12) 0.69190(8) 0.0812(3) 0.0365(10) Uani 1 1 d G . . H13 H 0.7409 0.7073 -0.0589 0.044 Uiso 1 1 calc R . . C14 C 0.75054(17) 0.74850(8) 0.2352(3) 0.0438(11) Uani 1 1 d G . . H14 H 0.7478 0.8026 0.2003 0.053 Uiso 1 1 calc R . . C15 C 0.75871(18) 0.72594(11) 0.4402(3) 0.0433(10) Uani 1 1 d G . . H15 H 0.7615 0.7646 0.5455 0.052 Uiso 1 1 calc R . . C16 C 0.76277(16) 0.64679(12) 0.4913(2) 0.0373(10) Uani 1 1 d G . . H16 H 0.7683 0.6314 0.6314 0.045 Uiso 1 1 calc R . . C17 C 0.75868(12) 0.59019(9) 0.3373(2) 0.0355(10) Uani 1 1 d G . . H17 H 0.7615 0.5361 0.3722 0.043 Uiso 1 1 calc R . . N21 N 0.93506(17) 0.43279(13) 0.4517(5) 0.0388(7) Uani 1 1 d . . . H21A H 0.8863 0.4425 0.5379 0.058 Uiso 1 1 calc R . . H21B H 0.9213 0.4511 0.3235 0.058 Uiso 1 1 calc R . . H21C H 0.9871 0.4574 0.4998 0.058 Uiso 1 1 calc R . . C22 C 0.9526(2) 0.34505(16) 0.4415(6) 0.0369(9) Uani 1 1 d . . . H22 H 0.8931 0.3176 0.4052 0.044 Uiso 1 1 calc R . . C23 C 0.9842(3) 0.31855(19) 0.6518(5) 0.0485(12) Uani 1 1 d . . . H23A H 0.9397 0.3368 0.7559 0.073 Uiso 1 1 calc R . . H23B H 1.0460 0.3405 0.6812 0.073 Uiso 1 1 calc R . . H23C H 0.9876 0.2611 0.6551 0.073 Uiso 1 1 calc R . . C24 C 1.0235(3) 0.3297(2) 0.2774(6) 0.0586(14) Uani 1 1 d . . . H24A H 1.0366 0.2733 0.2704 0.088 Uiso 1 1 calc R . . H24B H 1.0812 0.3581 0.3099 0.088 Uiso 1 1 calc R . . H24C H 0.9994 0.3477 0.1442 0.088 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 0.0389(4) 0.0280(3) 0.0338(4) 0.0002(5) 0.0033(5) 0.0026(3) O2 0.0604(14) 0.0285(11) 0.0297(12) -0.0094(11) -0.0040(12) -0.0049(11) O3 0.0384(11) 0.0277(10) 0.0415(13) -0.0025(10) 0.0146(11) 0.0040(10) O4 0.0433(11) 0.0248(10) 0.0387(13) 0.0034(11) -0.0172(12) 0.0009(10) C5 0.0432(17) 0.0217(14) 0.0179(16) -0.0042(14) -0.0058(16) 0.0035(14) C6 0.0424(17) 0.0579(19) 0.0253(18) -0.009(2) 0.0023(19) 0.0067(15) C7 0.0481(19) 0.065(2) 0.027(2) -0.0077(17) -0.0146(16) 0.0041(18) C8 0.051(2) 0.049(2) 0.046(2) 0.0061(19) 0.0135(19) -0.0076(19) C9 0.065(2) 0.078(2) 0.0206(19) 0.0034(18) 0.0002(18) -0.028(2) C10 0.056(2) 0.049(2) 0.0286(18) -0.0006(17) -0.0125(19) -0.0126(18) O11 0.0512(11) 0.0255(9) 0.0294(12) -0.0018(12) -0.0019(13) 0.0029(9) C12 0.0453(18) 0.0231(15) 0.0295(18) -0.0102(15) 0.0022(18) 0.0025(14) C13 0.0471(18) 0.0381(17) 0.0243(18) -0.0051(17) 0.0015(16) 0.0040(17) C14 0.066(2) 0.0264(16) 0.039(2) 0.0025(17) -0.014(2) 0.0026(17) C15 0.0546(18) 0.0369(17) 0.0384(19) -0.0130(18) -0.006(2) -0.0016(15) C16 0.0523(18) 0.0365(16) 0.0230(19) 0.0023(16) 0.0013(18) 0.0014(14) C17 0.0437(18) 0.0242(16) 0.0387(19) -0.0094(15) -0.0036(18) -0.0024(15) N21 0.0456(14) 0.0383(12) 0.0325(14) 0.0047(16) 0.0024(16) -0.0015(11) C22 0.0448(16) 0.0328(15) 0.0330(18) 0.0135(18) -0.003(2) -0.0010(14) C23 0.068(2) 0.0397(18) 0.038(2) 0.0059(18) -0.016(2) 0.0031(18) C24 0.072(3) 0.055(2) 0.049(3) 0.007(2) 0.006(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O3 1.451(2) . ? P1 O2 1.482(2) . ? P1 O11 1.617(2) . ? P1 O4 1.627(2) . ? O4 C5 1.379(3) . ? C5 C6 1.3900 . ? C5 C10 1.3900 . ? C6 C7 1.3900 . ? C6 H6 0.9500 . ? C7 C8 1.3900 . ? C7 H7 0.9500 . ? C8 C9 1.3900 . ? C8 H8 0.9500 . ? C9 C10 1.3900 . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O11 C12 1.383(2) . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N21 C22 1.517(4) . ? N21 H21A 0.9100 . ? N21 H21B 0.9100 . ? N21 H21C 0.9100 . ? C22 C24 1.495(5) . ? C22 C23 1.508(5) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 O3 P1 O2 119.49(13) . . ? O3 P1 O11 111.42(12) . . ? O2 P1 O11 105.36(13) . . ? O3 P1 O4 103.71(12) . . ? O2 P1 O4 111.55(12) . . ? O11 P1 O4 104.45(11) . . ? C5 O4 P1 124.65(15) . . ? O4 C5 C6 123.84(12) . . ? O4 C5 C10 116.15(12) . . ? C6 C5 C10 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 120.0 . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? C12 O11 P1 124.81(16) . . ? O11 C12 C13 116.67(11) . . ? O11 C12 C17 123.33(11) . . ? C13 C12 C17 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.0 . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C22 N21 H21A 109.5 . . ? C22 N21 H21B 109.5 . . ? H21A N21 H21B 109.5 . . ? C22 N21 H21C 109.5 . . ? H21A N21 H21C 109.5 . . ? H21B N21 H21C 109.5 . . ? C24 C22 C23 112.8(3) . . ? C24 C22 N21 108.4(3) . . ? C23 C22 N21 107.8(3) . . ? C24 C22 H22 109.3 . . ? C23 C22 H22 109.3 . . ? N21 C22 H22 109.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 O3 P1 O4 C5 160.45(17) . . . . ? O2 P1 O4 C5 -69.7(2) . . . . ? O11 P1 O4 C5 43.6(2) . . . . ? P1 O4 C5 C6 42.2(2) . . . . ? P1 O4 C5 C10 -138.58(15) . . . . ? O4 C5 C6 C7 179.17(12) . . . . ? C10 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C6 C7 C8 C9 0.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C5 0.0 . . . . ? O4 C5 C10 C9 -179.23(12) . . . . ? C6 C5 C10 C9 0.0 . . . . ? O3 P1 O11 C12 -37.1(2) . . . . ? O2 P1 O11 C12 -168.08(18) . . . . ? O4 P1 O11 C12 74.27(19) . . . . ? P1 O11 C12 C13 142.45(14) . . . . ? P1 O11 C12 C17 -38.5(2) . . . . ? O11 C12 C13 C14 179.13(13) . . . . ? C17 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C12 0.0 . . . . ? O11 C12 C17 C16 -179.07(14) . . . . ? C13 C12 C17 C16 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.413 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 894843' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_safin229new #TrackingRef 'web_deposit_cif_file_1_DamirSafin_1344110069.safin229-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N2 O3 P S' _chemical_formula_sum 'C16 H19 N2 O3 P S' _chemical_formula_weight 350.36 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 9.8501(12) _cell_length_b 11.0661(18) _cell_length_c 17.707(2) _cell_angle_alpha 92.032(11) _cell_angle_beta 92.940(10) _cell_angle_gamma 111.728(13) _cell_volume 1787.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1770 _cell_measurement_theta_min 2.9484 _cell_measurement_theta_max 25.2938 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8945 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details SADABS _exptl_special_details ; Two orientations were measured and merged with SADABS ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method ; '46 images, \D\F 2.0\%' '84 images, \D\F 2.0\%' ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17578 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0602 _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 -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.25 _reflns_number_total 6210 _reflns_number_gt 4690 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+1.6322P] 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 6210 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 P1 P 0.29723(6) 0.84967(6) 0.22851(3) 0.02823(14) Uani 1 1 d . . . O2 O 0.15917(16) 0.86733(16) 0.23951(9) 0.0368(4) Uani 1 1 d . . . O3 O 0.29917(16) 0.71251(15) 0.24668(9) 0.0331(4) Uani 1 1 d . . . C4 C 0.2372(2) 0.6439(2) 0.30993(13) 0.0301(6) Uani 1 1 d . . . C5 C 0.2703(3) 0.7018(2) 0.38210(14) 0.0347(6) Uani 1 1 d . . . H5 H 0.3317 0.7911 0.3905 0.042 Uiso 1 1 calc R . . C6 C 0.2121(3) 0.6270(2) 0.44220(15) 0.0404(6) Uani 1 1 d . . . H6 H 0.2331 0.6655 0.4924 0.048 Uiso 1 1 calc R . . C7 C 0.1241(3) 0.4970(2) 0.42972(15) 0.0423(7) Uani 1 1 d . . . H7 H 0.0865 0.4458 0.4713 0.051 Uiso 1 1 calc R . . C8 C 0.0904(3) 0.4412(2) 0.35631(15) 0.0400(7) Uani 1 1 d . . . H8 H 0.0282 0.3521 0.3478 0.048 Uiso 1 1 calc R . . C9 C 0.1466(3) 0.5142(2) 0.29580(15) 0.0374(6) Uani 1 1 d . . . H9 H 0.1237 0.4765 0.2455 0.045 Uiso 1 1 calc R . . O10 O 0.34593(16) 0.84870(15) 0.14586(9) 0.0329(4) Uani 1 1 d . . . C11 C 0.3506(2) 0.9514(2) 0.09937(13) 0.0321(6) Uani 1 1 d . . . C12 C 0.2264(3) 0.9372(2) 0.05406(14) 0.0376(7) Uani 1 1 d . . . H12 H 0.1393 0.8621 0.0554 0.045 Uiso 1 1 calc R . . C13 C 0.2329(3) 1.0355(3) 0.00677(15) 0.0453(7) Uani 1 1 d . . . H13 H 0.1488 1.0286 -0.0246 0.054 Uiso 1 1 calc R . . C14 C 0.3609(3) 1.1442(3) 0.00453(16) 0.0497(8) Uani 1 1 d . . . H14 H 0.3643 1.2114 -0.0281 0.060 Uiso 1 1 calc R . . C15 C 0.4840(3) 1.1544(3) 0.05008(16) 0.0481(8) Uani 1 1 d . . . H15 H 0.5715 1.2290 0.0484 0.058 Uiso 1 1 calc R . . C16 C 0.4808(3) 1.0578(3) 0.09776(15) 0.0402(7) Uani 1 1 d . . . H16 H 0.5652 1.0639 0.1286 0.048 Uiso 1 1 calc R . . N17 N 0.43655(19) 0.96348(17) 0.27737(11) 0.0298(5) Uani 1 1 d . . . H17 H 0.5229 0.9769 0.2602 0.036 Uiso 1 1 calc R . . C18 C 0.4388(2) 1.0410(2) 0.34105(14) 0.0317(6) Uani 1 1 d . . . S19 S 0.60033(8) 1.11892(9) 0.38947(5) 0.0705(3) Uani 1 1 d . . . N20 N 0.3116(2) 1.04405(19) 0.35887(12) 0.0386(5) Uani 1 1 d . . . H20 H 0.2355 1.0046 0.3266 0.046 Uiso 1 1 calc R . . C21 C 0.2863(3) 1.1077(3) 0.42790(15) 0.0478(7) Uani 1 1 d . . . H21 H 0.3817 1.1534 0.4579 0.057 Uiso 1 1 calc R . . C22 C 0.1850(4) 0.9997(4) 0.47398(19) 0.0805(12) Uani 1 1 d . . . H22A H 0.0902 0.9568 0.4454 0.121 Uiso 1 1 calc R . . H22B H 0.1705 1.0378 0.5223 0.121 Uiso 1 1 calc R . . H22C H 0.2297 0.9355 0.4837 0.121 Uiso 1 1 calc R . . C23 C 0.2192(4) 1.2042(3) 0.4082(2) 0.0807(10) Uani 1 1 d . . . H23A H 0.2820 1.2671 0.3750 0.121 Uiso 1 1 calc R . . H23B H 0.2091 1.2502 0.4546 0.121 Uiso 1 1 calc R . . H23C H 0.1223 1.1587 0.3820 0.121 Uiso 1 1 calc R . . P31 P 0.81675(6) 0.89548(6) 0.25505(4) 0.02832(15) Uani 1 1 d . . . O32 O 0.66546(15) 0.88589(14) 0.23854(10) 0.0339(4) Uani 1 1 d . . . O33 O 0.94246(16) 1.03455(15) 0.26076(10) 0.0355(4) Uani 1 1 d . . . C34 C 0.9462(2) 1.1255(2) 0.20582(15) 0.0352(6) Uani 1 1 d . . . C35 C 1.0465(3) 1.1468(2) 0.15208(16) 0.0437(7) Uani 1 1 d . . . H35 H 1.1103 1.1001 0.1509 0.052 Uiso 1 1 calc R . . C36 C 1.0528(3) 1.2380(3) 0.09949(18) 0.0531(9) Uani 1 1 d . . . H36 H 1.1188 1.2519 0.0605 0.064 Uiso 1 1 calc R . . C37 C 0.9636(3) 1.3086(3) 0.10346(18) 0.0522(9) Uani 1 1 d . . . H37 H 0.9692 1.3718 0.0676 0.063 Uiso 1 1 calc R . . C38 C 0.8661(3) 1.2877(3) 0.15959(18) 0.0504(8) Uani 1 1 d . . . H38 H 0.8051 1.3370 0.1621 0.060 Uiso 1 1 calc R . . C39 C 0.8565(3) 1.1958(2) 0.21200(16) 0.0405(7) Uani 1 1 d . . . H39 H 0.7904 1.1813 0.2510 0.049 Uiso 1 1 calc R . . O40 O 0.85149(17) 0.85414(16) 0.33574(9) 0.0371(4) Uani 1 1 d . . . C41 C 0.7709(2) 0.7250(2) 0.35494(13) 0.0350(6) Uani 1 1 d . . . C42 C 0.6348(3) 0.6971(3) 0.38293(15) 0.0461(7) Uani 1 1 d . . . H42 H 0.5947 0.7626 0.3884 0.055 Uiso 1 1 calc R . . C43 C 0.5585(3) 0.5711(3) 0.40285(17) 0.0541(8) Uani 1 1 d . . . H43 H 0.4653 0.5501 0.4228 0.065 Uiso 1 1 calc R . . C44 C 0.6162(3) 0.4756(3) 0.39410(17) 0.0562(8) Uani 1 1 d . . . H44 H 0.5628 0.3892 0.4073 0.067 Uiso 1 1 calc R . . C45 C 0.7538(3) 0.5078(3) 0.36570(17) 0.0532(8) Uani 1 1 d . . . H45 H 0.7943 0.4426 0.3600 0.064 Uiso 1 1 calc R . . C46 C 0.8327(3) 0.6337(3) 0.34565(15) 0.0457(7) Uani 1 1 d . . . H46 H 0.9263 0.6555 0.3261 0.055 Uiso 1 1 calc R . . N47 N 0.86315(18) 0.80894(17) 0.19131(11) 0.0276(5) Uani 1 1 d . . . H47 H 0.9556 0.8405 0.1806 0.033 Uiso 1 1 calc R . . C48 C 0.7755(2) 0.6917(2) 0.15173(13) 0.0291(6) Uani 1 1 d . . . S49 S 0.86008(7) 0.60944(6) 0.10425(4) 0.04227(17) Uani 1 1 d . . . N50 N 0.6311(2) 0.65468(18) 0.15443(11) 0.0334(5) Uani 1 1 d . . . H50 H 0.5982 0.7094 0.1771 0.040 Uiso 1 1 calc R . . C51 C 0.5208(3) 0.5287(2) 0.12237(15) 0.0411(7) Uani 1 1 d . . . H51 H 0.5640 0.4948 0.0806 0.049 Uiso 1 1 calc R . . C52 C 0.3866(3) 0.5503(3) 0.09002(17) 0.0495(8) Uani 1 1 d . . . H52A H 0.3429 0.5828 0.1306 0.074 Uiso 1 1 calc R . . H52B H 0.3151 0.4677 0.0674 0.074 Uiso 1 1 calc R . . H52C H 0.4151 0.6142 0.0511 0.074 Uiso 1 1 calc R . . C53 C 0.4839(4) 0.4318(3) 0.1835(2) 0.0638(10) Uani 1 1 d . . . H53A H 0.5735 0.4218 0.2036 0.096 Uiso 1 1 calc R . . H53B H 0.4142 0.3475 0.1621 0.096 Uiso 1 1 calc R . . H53C H 0.4402 0.4635 0.2245 0.096 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 0.0196(2) 0.0390(3) 0.0302(3) -0.0025(2) 0.0030(2) 0.0159(2) O2 0.0227(7) 0.0564(9) 0.0365(9) -0.0059(7) 0.0009(7) 0.0219(6) O3 0.0304(7) 0.0379(8) 0.0335(9) -0.0007(7) 0.0089(7) 0.0151(6) C4 0.0229(10) 0.0372(11) 0.0358(13) 0.0042(10) 0.0057(9) 0.0171(8) C5 0.0361(12) 0.0336(11) 0.0367(13) -0.0023(10) 0.0041(11) 0.0159(9) C6 0.0481(13) 0.0441(12) 0.0365(14) 0.0022(11) 0.0050(11) 0.0257(10) C7 0.0421(12) 0.0510(13) 0.0437(15) 0.0122(11) 0.0154(11) 0.0262(10) C8 0.0334(12) 0.0363(12) 0.0492(15) 0.0003(11) 0.0073(11) 0.0115(10) C9 0.0323(12) 0.0407(12) 0.0396(14) -0.0028(11) 0.0047(11) 0.0140(10) O10 0.0313(7) 0.0426(8) 0.0303(8) 0.0005(7) 0.0069(7) 0.0197(6) C11 0.0308(11) 0.0421(11) 0.0276(12) 0.0023(10) 0.0072(10) 0.0180(9) C12 0.0263(11) 0.0501(13) 0.0363(13) 0.0002(11) 0.0049(10) 0.0138(10) C13 0.0343(12) 0.0685(16) 0.0359(14) 0.0096(12) 0.0008(11) 0.0220(11) C14 0.0450(14) 0.0627(15) 0.0455(15) 0.0202(13) 0.0087(12) 0.0227(12) C15 0.0389(14) 0.0517(15) 0.0466(16) 0.0081(13) 0.0041(12) 0.0080(12) C16 0.0280(11) 0.0536(14) 0.0381(14) -0.0001(11) 0.0012(11) 0.0147(10) N17 0.0174(8) 0.0393(9) 0.0342(10) -0.0066(8) 0.0033(8) 0.0129(7) C18 0.0304(11) 0.0311(10) 0.0366(13) -0.0010(10) 0.0016(10) 0.0154(9) S19 0.0290(3) 0.0917(5) 0.0827(5) -0.0505(4) -0.0096(4) 0.0197(3) N20 0.0306(9) 0.0555(11) 0.0378(11) -0.0114(9) -0.0005(9) 0.0271(8) C21 0.0400(12) 0.0671(15) 0.0438(15) -0.0229(12) -0.0031(12) 0.0319(11) C22 0.088(2) 0.101(2) 0.0510(19) -0.0183(18) 0.0192(18) 0.033(2) C23 0.0866(18) 0.0919(17) 0.084(2) -0.0485(16) -0.0323(18) 0.0672(14) P31 0.0169(2) 0.0331(3) 0.0360(3) -0.0031(2) 0.0019(2) 0.0109(2) O32 0.0213(7) 0.0355(8) 0.0472(10) -0.0058(7) 0.0026(7) 0.0139(6) O33 0.0222(7) 0.0348(8) 0.0481(10) -0.0013(7) -0.0010(7) 0.0098(6) C34 0.0209(11) 0.0310(11) 0.0478(15) -0.0054(11) -0.0014(11) 0.0040(9) C35 0.0297(12) 0.0410(13) 0.0578(17) -0.0047(12) 0.0066(12) 0.0105(10) C36 0.0434(15) 0.0410(14) 0.0616(18) -0.0008(14) 0.0153(14) -0.0010(12) C37 0.0513(16) 0.0340(13) 0.0609(19) 0.0042(13) -0.0034(15) 0.0047(12) C38 0.0373(13) 0.0343(12) 0.077(2) -0.0040(13) -0.0020(14) 0.0115(11) C39 0.0298(12) 0.0328(12) 0.0548(16) -0.0063(12) 0.0032(12) 0.0077(10) O40 0.0251(8) 0.0504(9) 0.0333(9) -0.0029(7) -0.0002(7) 0.0119(7) C41 0.0271(11) 0.0506(13) 0.0276(12) 0.0048(10) 0.0023(10) 0.0145(10) C42 0.0372(12) 0.0702(16) 0.0375(14) 0.0084(12) 0.0098(11) 0.0262(11) C43 0.0375(13) 0.0785(17) 0.0533(16) 0.0280(14) 0.0164(12) 0.0259(12) C44 0.0425(14) 0.0686(16) 0.0614(18) 0.0344(14) 0.0087(13) 0.0219(13) C45 0.0428(13) 0.0668(15) 0.0630(18) 0.0250(14) 0.0083(13) 0.0331(11) C46 0.0292(11) 0.0690(15) 0.0459(15) 0.0179(13) 0.0075(11) 0.0245(11) N47 0.0151(8) 0.0302(9) 0.0379(11) 0.0001(8) 0.0052(8) 0.0085(7) C48 0.0277(10) 0.0332(11) 0.0284(12) 0.0063(9) 0.0043(9) 0.0131(9) S49 0.0399(3) 0.0426(3) 0.0499(4) -0.0036(3) 0.0161(3) 0.0207(2) N50 0.0242(9) 0.0345(9) 0.0409(11) -0.0038(9) 0.0079(9) 0.0101(7) C51 0.0327(12) 0.0392(13) 0.0432(15) -0.0098(11) 0.0081(11) 0.0039(10) C52 0.0351(14) 0.0501(15) 0.0497(16) 0.0005(13) 0.0032(13) 0.0003(12) C53 0.0626(19) 0.0402(15) 0.076(2) 0.0101(15) 0.0036(17) 0.0043(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 P1 O2 1.4652(17) . ? P1 O10 1.5643(17) . ? P1 O3 1.5695(17) . ? P1 N17 1.6550(18) . ? O3 C4 1.411(3) . ? C4 C5 1.376(3) . ? C4 C9 1.387(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(4) . ? C7 H7 0.9500 . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? O10 C11 1.415(3) . ? C11 C12 1.383(3) . ? C11 C16 1.385(3) . ? C12 C13 1.381(4) . ? C12 H12 0.9500 . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 C16 1.378(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N17 C18 1.386(3) . ? N17 H17 0.8800 . ? C18 N20 1.320(3) . ? C18 S19 1.674(2) . ? N20 C21 1.467(3) . ? N20 H20 0.8800 . ? C21 C23 1.492(4) . ? C21 C22 1.536(4) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? P31 O32 1.4674(16) . ? P31 O33 1.5739(16) . ? P31 O40 1.5748(18) . ? P31 N47 1.643(2) . ? O33 C34 1.417(3) . ? C34 C35 1.370(4) . ? C34 C39 1.382(4) . ? C35 C36 1.384(4) . ? C35 H35 0.9500 . ? C36 C37 1.377(5) . ? C36 H36 0.9500 . ? C37 C38 1.384(4) . ? C37 H37 0.9500 . ? C38 C39 1.382(4) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? O40 C41 1.418(3) . ? C41 C46 1.368(4) . ? C41 C42 1.382(3) . ? C42 C43 1.385(4) . ? C42 H42 0.9500 . ? C43 C44 1.380(5) . ? C43 H43 0.9500 . ? C44 C45 1.393(4) . ? C44 H44 0.9500 . ? C45 C46 1.390(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N47 C48 1.402(3) . ? N47 H47 0.8800 . ? C48 N50 1.331(3) . ? C48 S49 1.676(2) . ? N50 C51 1.485(3) . ? N50 H50 0.8800 . ? C51 C53 1.512(4) . ? C51 C52 1.516(4) . ? C51 H51 1.0000 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 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 O2 P1 O10 118.01(10) . . ? O2 P1 O3 115.64(9) . . ? O10 P1 O3 96.10(9) . . ? O2 P1 N17 111.40(10) . . ? O10 P1 N17 105.51(9) . . ? O3 P1 N17 108.77(10) . . ? C4 O3 P1 124.09(15) . . ? C5 C4 C9 122.0(2) . . ? C5 C4 O3 121.43(19) . . ? C9 C4 O3 116.5(2) . . ? C4 C5 C6 118.6(2) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C4 118.6(2) . . ? C8 C9 H9 120.7 . . ? C4 C9 H9 120.7 . . ? C11 O10 P1 119.65(15) . . ? C12 C11 C16 122.8(2) . . ? C12 C11 O10 118.05(19) . . ? C16 C11 O10 119.0(2) . . ? C13 C12 C11 117.9(2) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C14 120.7(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C11 117.9(2) . . ? C15 C16 H16 121.0 . . ? C11 C16 H16 121.0 . . ? C18 N17 P1 130.27(15) . . ? C18 N17 H17 114.9 . . ? P1 N17 H17 114.9 . . ? N20 C18 N17 116.47(19) . . ? N20 C18 S19 125.89(18) . . ? N17 C18 S19 117.63(17) . . ? C18 N20 C21 125.5(2) . . ? C18 N20 H20 117.2 . . ? C21 N20 H20 117.2 . . ? N20 C21 C23 110.3(2) . . ? N20 C21 C22 107.0(2) . . ? C23 C21 C22 111.4(3) . . ? N20 C21 H21 109.4 . . ? C23 C21 H21 109.4 . . ? C22 C21 H21 109.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O32 P31 O33 118.38(10) . . ? O32 P31 O40 115.73(10) . . ? O33 P31 O40 96.72(9) . . ? O32 P31 N47 110.73(9) . . ? O33 P31 N47 105.91(9) . . ? O40 P31 N47 108.07(10) . . ? C34 O33 P31 120.31(14) . . ? C35 C34 C39 122.8(3) . . ? C35 C34 O33 118.3(2) . . ? C39 C34 O33 118.7(2) . . ? C34 C35 C36 118.4(3) . . ? C34 C35 H35 120.8 . . ? C36 C35 H35 120.8 . . ? C37 C36 C35 120.3(3) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C38 120.1(3) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C39 C38 C37 120.6(3) . . ? C39 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C34 C39 C38 117.8(3) . . ? C34 C39 H39 121.1 . . ? C38 C39 H39 121.1 . . ? C41 O40 P31 117.89(14) . . ? C46 C41 C42 122.9(2) . . ? C46 C41 O40 118.2(2) . . ? C42 C41 O40 118.9(2) . . ? C41 C42 C43 118.3(3) . . ? C41 C42 H42 120.9 . . ? C43 C42 H42 120.9 . . ? C44 C43 C42 120.8(3) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C43 C44 C45 119.1(3) . . ? C43 C44 H44 120.4 . . ? C45 C44 H44 120.4 . . ? C46 C45 C44 121.1(3) . . ? C46 C45 H45 119.4 . . ? C44 C45 H45 119.4 . . ? C41 C46 C45 117.8(2) . . ? C41 C46 H46 121.1 . . ? C45 C46 H46 121.1 . . ? C48 N47 P31 128.80(15) . . ? C48 N47 H47 115.6 . . ? P31 N47 H47 115.6 . . ? N50 C48 N47 117.3(2) . . ? N50 C48 S49 125.05(17) . . ? N47 C48 S49 117.68(16) . . ? C48 N50 C51 125.4(2) . . ? C48 N50 H50 117.3 . . ? C51 N50 H50 117.3 . . ? N50 C51 C53 109.2(2) . . ? N50 C51 C52 109.4(2) . . ? C53 C51 C52 111.9(2) . . ? N50 C51 H51 108.8 . . ? C53 C51 H51 108.8 . . ? C52 C51 H51 108.8 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 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 O3 C4 -42.09(19) . . . . ? O10 P1 O3 C4 -167.20(16) . . . . ? N17 P1 O3 C4 84.11(17) . . . . ? P1 O3 C4 C5 -51.4(3) . . . . ? P1 O3 C4 C9 131.26(19) . . . . ? C9 C4 C5 C6 0.7(4) . . . . ? O3 C4 C5 C6 -176.5(2) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? C5 C6 C7 C8 -1.5(4) . . . . ? C6 C7 C8 C9 1.2(4) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C5 C4 C9 C8 -1.1(4) . . . . ? O3 C4 C9 C8 176.3(2) . . . . ? O2 P1 O10 C11 51.54(18) . . . . ? O3 P1 O10 C11 174.89(15) . . . . ? N17 P1 O10 C11 -73.67(17) . . . . ? P1 O10 C11 C12 -91.0(2) . . . . ? P1 O10 C11 C16 92.7(2) . . . . ? C16 C11 C12 C13 -1.6(4) . . . . ? O10 C11 C12 C13 -177.7(2) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? C14 C15 C16 C11 -0.8(4) . . . . ? C12 C11 C16 C15 1.7(4) . . . . ? O10 C11 C16 C15 177.8(2) . . . . ? O2 P1 N17 C18 22.7(2) . . . . ? O10 P1 N17 C18 151.9(2) . . . . ? O3 P1 N17 C18 -105.9(2) . . . . ? P1 N17 C18 N20 -13.9(3) . . . . ? P1 N17 C18 S19 164.57(14) . . . . ? N17 C18 N20 C21 173.0(2) . . . . ? S19 C18 N20 C21 -5.4(4) . . . . ? C18 N20 C21 C23 123.9(3) . . . . ? C18 N20 C21 C22 -114.8(3) . . . . ? O32 P31 O33 C34 -45.3(2) . . . . ? O40 P31 O33 C34 -169.37(18) . . . . ? N47 P31 O33 C34 79.63(19) . . . . ? P31 O33 C34 C35 -104.4(2) . . . . ? P31 O33 C34 C39 80.3(2) . . . . ? C39 C34 C35 C36 -3.4(4) . . . . ? O33 C34 C35 C36 -178.4(2) . . . . ? C34 C35 C36 C37 2.5(4) . . . . ? C35 C36 C37 C38 -0.7(4) . . . . ? C36 C37 C38 C39 -0.2(4) . . . . ? C35 C34 C39 C38 2.4(4) . . . . ? O33 C34 C39 C38 177.5(2) . . . . ? C37 C38 C39 C34 -0.6(4) . . . . ? O32 P31 O40 C41 59.6(2) . . . . ? O33 P31 O40 C41 -174.39(17) . . . . ? N47 P31 O40 C41 -65.20(18) . . . . ? P31 O40 C41 C46 96.7(2) . . . . ? P31 O40 C41 C42 -84.0(2) . . . . ? C46 C41 C42 C43 0.5(4) . . . . ? O40 C41 C42 C43 -178.8(2) . . . . ? C41 C42 C43 C44 -0.8(4) . . . . ? C42 C43 C44 C45 0.8(4) . . . . ? C43 C44 C45 C46 -0.5(4) . . . . ? C42 C41 C46 C45 -0.2(4) . . . . ? O40 C41 C46 C45 179.0(2) . . . . ? C44 C45 C46 C41 0.2(4) . . . . ? O32 P31 N47 C48 -33.3(2) . . . . ? O33 P31 N47 C48 -162.8(2) . . . . ? O40 P31 N47 C48 94.4(2) . . . . ? P31 N47 C48 N50 13.4(3) . . . . ? P31 N47 C48 S49 -167.03(13) . . . . ? N47 C48 N50 C51 -174.1(2) . . . . ? S49 C48 N50 C51 6.3(3) . . . . ? C48 N50 C51 C53 93.8(3) . . . . ? C48 N50 C51 C52 -143.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.473 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 894844' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_safin238 #TrackingRef 'web_deposit_cif_file_2_DamirSafin_1344110069.safin238.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 N4 Ni O6 P2 S2' _chemical_formula_sum 'C32 H36 N4 Ni O6 P2 S2' _chemical_formula_weight 757.42 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 '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 12.060(2) _cell_length_b 10.7171(10) _cell_length_c 13.9639(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.435(11) _cell_angle_gamma 90.00 _cell_volume 1804.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.9192 _cell_measurement_theta_max 25.5549 _exptl_crystal_description block _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.789 _exptl_absorpt_correction_T_min 0.88572 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '61 images, \D\F 2.5\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9499 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.61 _reflns_number_total 3334 _reflns_number_gt 2761 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.6995P] 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 3334 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.0000 0.0000 0.5000 0.03297(15) Uani 1 2 d S . . S2 S 0.08714(6) 0.06198(6) 0.63316(5) 0.0440(2) Uani 1 1 d . . . C3 C 0.0385(2) 0.2012(2) 0.58604(17) 0.0329(5) Uani 1 1 d . . . N4 N 0.06198(17) 0.31302(18) 0.61898(15) 0.0370(5) Uani 1 1 d . . . H4 H 0.0275 0.3759 0.5948 0.044 Uiso 1 1 calc R . . C5 C 0.1449(2) 0.3363(2) 0.69581(18) 0.0392(6) Uani 1 1 d . . . H5 H 0.1506 0.2613 0.7357 0.047 Uiso 1 1 calc R . . C6 C 0.1060(3) 0.4429(3) 0.7574(2) 0.0572(8) Uani 1 1 d . . . H6A H 0.0950 0.5156 0.7183 0.086 Uiso 1 1 calc R . . H6B H 0.1608 0.4604 0.8057 0.086 Uiso 1 1 calc R . . H6C H 0.0374 0.4206 0.7873 0.086 Uiso 1 1 calc R . . C7 C 0.2569(3) 0.3604(4) 0.6508(3) 0.0730(10) Uani 1 1 d . . . H7A H 0.2782 0.2894 0.6134 0.109 Uiso 1 1 calc R . . H7B H 0.3112 0.3746 0.7003 0.109 Uiso 1 1 calc R . . H7C H 0.2522 0.4327 0.6104 0.109 Uiso 1 1 calc R . . N8 N -0.02542(17) 0.17471(18) 0.50887(14) 0.0348(5) Uani 1 1 d . . . P9 P -0.08109(5) 0.27514(5) 0.43466(4) 0.03186(17) Uani 1 1 d . . . O10 O -0.08642(15) 0.40321(14) 0.47183(13) 0.0408(4) Uani 1 1 d . . . O11 O -0.01887(15) 0.25867(16) 0.33498(12) 0.0400(4) Uani 1 1 d . . . C12 C 0.0980(2) 0.2695(2) 0.32907(19) 0.0411(6) Uani 1 1 d . . . C13 C 0.1523(3) 0.1767(3) 0.2796(3) 0.0683(10) Uani 1 1 d . . . H13 H 0.1136 0.1088 0.2548 0.082 Uiso 1 1 calc R . . C14 C 0.2666(3) 0.1874(4) 0.2674(4) 0.0915(14) Uani 1 1 d . . . H14 H 0.3044 0.1259 0.2339 0.110 Uiso 1 1 calc R . . C15 C 0.3238(3) 0.2863(4) 0.3039(3) 0.0812(11) Uani 1 1 d . . . H15 H 0.3999 0.2928 0.2945 0.097 Uiso 1 1 calc R . . C16 C 0.2689(3) 0.3760(3) 0.3547(3) 0.0671(9) Uani 1 1 d . . . H16 H 0.3083 0.4426 0.3808 0.081 Uiso 1 1 calc R . . C17 C 0.1541(2) 0.3688(3) 0.3676(2) 0.0490(7) Uani 1 1 d . . . H17 H 0.1167 0.4301 0.4017 0.059 Uiso 1 1 calc R . . O18 O -0.19593(13) 0.21822(15) 0.39998(12) 0.0380(4) Uani 1 1 d . . . C19 C -0.2878(2) 0.2128(2) 0.46245(19) 0.0408(6) Uani 1 1 d . . . C20 C -0.3673(3) 0.3038(3) 0.4585(3) 0.0632(9) Uani 1 1 d . . . H20 H -0.3589 0.3729 0.4190 0.076 Uiso 1 1 calc R . . C21 C -0.4618(3) 0.2903(4) 0.5157(3) 0.0848(12) Uani 1 1 d . . . H21 H -0.5169 0.3510 0.5137 0.102 Uiso 1 1 calc R . . C22 C -0.4738(3) 0.1896(4) 0.5739(3) 0.0885(13) Uani 1 1 d . . . H22 H -0.5365 0.1818 0.6119 0.106 Uiso 1 1 calc R . . C23 C -0.3941(3) 0.1012(4) 0.5762(3) 0.0897(13) Uani 1 1 d . . . H23 H -0.4025 0.0323 0.6160 0.108 Uiso 1 1 calc R . . C24 C -0.3006(3) 0.1111(3) 0.5208(2) 0.0651(9) Uani 1 1 d . . . H24 H -0.2465 0.0493 0.5229 0.078 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 0.0411(3) 0.0230(2) 0.0347(3) -0.00045(16) -0.00922(19) 0.00283(17) S2 0.0608(4) 0.0285(3) 0.0425(4) 0.0005(3) -0.0195(3) 0.0060(3) C3 0.0353(13) 0.0325(12) 0.0309(12) -0.0016(10) -0.0033(10) 0.0038(10) N4 0.0461(12) 0.0260(10) 0.0386(11) -0.0012(8) -0.0147(10) 0.0047(9) C5 0.0497(15) 0.0312(12) 0.0366(13) -0.0019(10) -0.0155(12) 0.0011(11) C6 0.084(2) 0.0446(15) 0.0421(16) -0.0094(13) -0.0192(16) 0.0106(16) C7 0.0439(17) 0.102(3) 0.073(2) -0.013(2) -0.0123(17) -0.0045(18) N8 0.0426(12) 0.0262(9) 0.0354(11) -0.0017(8) -0.0093(9) 0.0036(9) P9 0.0366(3) 0.0248(3) 0.0340(3) 0.0000(2) -0.0073(3) 0.0029(2) O10 0.0459(10) 0.0281(8) 0.0482(10) -0.0031(7) -0.0101(8) 0.0060(7) O11 0.0412(10) 0.0418(9) 0.0368(9) 0.0009(8) -0.0030(8) 0.0013(8) C12 0.0425(14) 0.0383(13) 0.0424(14) 0.0056(11) 0.0020(12) 0.0022(12) C13 0.061(2) 0.0582(19) 0.085(3) -0.0250(18) 0.0114(19) 0.0019(16) C14 0.061(2) 0.089(3) 0.125(4) -0.040(3) 0.020(2) 0.013(2) C15 0.052(2) 0.089(3) 0.103(3) -0.012(2) 0.013(2) 0.002(2) C16 0.0518(18) 0.067(2) 0.083(2) -0.0004(19) 0.0034(17) -0.0121(17) C17 0.0492(16) 0.0438(14) 0.0542(17) -0.0015(13) 0.0057(13) -0.0021(13) O18 0.0371(9) 0.0400(9) 0.0367(9) -0.0020(7) -0.0085(8) 0.0004(8) C19 0.0339(13) 0.0444(14) 0.0440(15) -0.0072(12) -0.0056(11) 0.0013(11) C20 0.0528(18) 0.0565(18) 0.080(2) 0.0045(16) 0.0006(17) 0.0098(15) C21 0.048(2) 0.097(3) 0.110(3) -0.005(3) 0.011(2) 0.026(2) C22 0.061(2) 0.112(3) 0.093(3) 0.013(3) 0.022(2) 0.002(2) C23 0.075(3) 0.099(3) 0.095(3) 0.037(2) 0.026(2) 0.010(2) C24 0.0566(19) 0.067(2) 0.072(2) 0.0196(17) 0.0091(17) 0.0098(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N8 1.9015(19) . ? Ni1 N8 1.9015(19) 3_556 ? Ni1 S2 2.2301(7) . ? Ni1 S2 2.2301(7) 3_556 ? Ni1 C3 2.510(2) 3_556 ? Ni1 C3 2.510(2) . ? S2 C3 1.732(2) . ? C3 N4 1.313(3) . ? C3 N8 1.350(3) . ? N4 C5 1.483(3) . ? N4 H4 0.8600 . ? C5 C6 1.507(4) . ? C5 C7 1.515(4) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? N8 P9 1.635(2) . ? P9 O10 1.4690(17) . ? P9 O18 1.5857(17) . ? P9 O11 1.5960(19) . ? O11 C12 1.418(3) . ? C12 C17 1.369(4) . ? C12 C13 1.379(4) . ? C13 C14 1.395(5) . ? C13 H13 0.9300 . ? C14 C15 1.362(5) . ? C14 H14 0.9300 . ? C15 C16 1.368(5) . ? C15 H15 0.9300 . ? C16 C17 1.399(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? O18 C19 1.417(3) . ? C19 C20 1.368(4) . ? C19 C24 1.370(4) . ? C20 C21 1.404(5) . ? C20 H20 0.9300 . ? C21 C22 1.360(6) . ? C21 H21 0.9300 . ? C22 C23 1.350(6) . ? C22 H22 0.9300 . ? C23 C24 1.377(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Ni1 N8 180.0 . 3_556 ? N8 Ni1 S2 74.19(6) . . ? N8 Ni1 S2 105.81(6) 3_556 . ? N8 Ni1 S2 105.81(6) . 3_556 ? N8 Ni1 S2 74.19(6) 3_556 3_556 ? S2 Ni1 S2 180.0 . 3_556 ? N8 Ni1 C3 147.98(8) . 3_556 ? N8 Ni1 C3 32.02(8) 3_556 3_556 ? S2 Ni1 C3 137.66(5) . 3_556 ? S2 Ni1 C3 42.34(5) 3_556 3_556 ? N8 Ni1 C3 32.02(8) . . ? N8 Ni1 C3 147.97(8) 3_556 . ? S2 Ni1 C3 42.34(5) . . ? S2 Ni1 C3 137.66(5) 3_556 . ? C3 Ni1 C3 180.0 3_556 . ? C3 S2 Ni1 77.52(8) . . ? N4 C3 N8 126.3(2) . . ? N4 C3 S2 125.56(18) . . ? N8 C3 S2 108.14(16) . . ? N4 C3 Ni1 171.83(19) . . ? N8 C3 Ni1 48.30(11) . . ? S2 C3 Ni1 60.15(7) . . ? C3 N4 C5 123.32(19) . . ? C3 N4 H4 118.3 . . ? C5 N4 H4 118.3 . . ? N4 C5 C6 109.2(2) . . ? N4 C5 C7 109.1(2) . . ? C6 C5 C7 112.9(3) . . ? N4 C5 H5 108.5 . . ? C6 C5 H5 108.5 . . ? C7 C5 H5 108.5 . . ? 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 . . ? C3 N8 P9 126.61(16) . . ? C3 N8 Ni1 99.68(14) . . ? P9 N8 Ni1 132.27(12) . . ? O10 P9 O18 115.27(10) . . ? O10 P9 O11 115.69(10) . . ? O18 P9 O11 96.11(9) . . ? O10 P9 N8 114.21(10) . . ? O18 P9 N8 107.09(10) . . ? O11 P9 N8 106.65(10) . . ? C12 O11 P9 121.07(16) . . ? C17 C12 C13 121.5(3) . . ? C17 C12 O11 121.9(2) . . ? C13 C12 O11 116.5(3) . . ? C12 C13 C14 118.4(3) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 118.6(3) . . ? C12 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C19 O18 P9 120.87(15) . . ? C20 C19 C24 120.6(3) . . ? C20 C19 O18 119.8(3) . . ? C24 C19 O18 119.4(2) . . ? C19 C20 C21 118.4(3) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 120.8(4) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 119.5(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 121.2(4) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C19 C24 C23 119.5(3) . . ? C19 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? 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 N8 Ni1 S2 C3 -3.99(11) . . . . ? N8 Ni1 S2 C3 176.01(11) 3_556 . . . ? C3 Ni1 S2 C3 180.0 3_556 . . . ? Ni1 S2 C3 N4 -173.0(2) . . . . ? Ni1 S2 C3 N8 5.69(15) . . . . ? N8 Ni1 C3 N8 180.0 3_556 . . . ? S2 Ni1 C3 N8 -172.8(2) . . . . ? S2 Ni1 C3 N8 7.2(2) 3_556 . . . ? N8 Ni1 C3 S2 172.8(2) . . . . ? N8 Ni1 C3 S2 -7.3(2) 3_556 . . . ? S2 Ni1 C3 S2 180.0 3_556 . . . ? N8 C3 N4 C5 -171.3(2) . . . . ? S2 C3 N4 C5 7.2(4) . . . . ? C3 N4 C5 C6 -144.6(3) . . . . ? C3 N4 C5 C7 91.6(3) . . . . ? N4 C3 N8 P9 4.5(4) . . . . ? S2 C3 N8 P9 -174.21(15) . . . . ? Ni1 C3 N8 P9 -167.6(3) . . . . ? N4 C3 N8 Ni1 172.1(2) . . . . ? S2 C3 N8 Ni1 -6.61(18) . . . . ? S2 Ni1 N8 C3 5.07(14) . . . . ? S2 Ni1 N8 C3 -174.93(14) 3_556 . . . ? C3 Ni1 N8 C3 180.0 3_556 . . . ? S2 Ni1 N8 P9 171.59(18) . . . . ? S2 Ni1 N8 P9 -8.41(18) 3_556 . . . ? C3 Ni1 N8 P9 -13.5(3) 3_556 . . . ? C3 Ni1 N8 P9 166.5(3) . . . . ? C3 N8 P9 O10 -17.8(3) . . . . ? Ni1 N8 P9 O10 178.81(14) . . . . ? C3 N8 P9 O18 -146.7(2) . . . . ? Ni1 N8 P9 O18 49.92(19) . . . . ? C3 N8 P9 O11 111.3(2) . . . . ? Ni1 N8 P9 O11 -52.09(19) . . . . ? O10 P9 O11 C12 72.42(19) . . . . ? O18 P9 O11 C12 -165.72(17) . . . . ? N8 P9 O11 C12 -55.82(19) . . . . ? P9 O11 C12 C17 -49.9(3) . . . . ? P9 O11 C12 C13 132.2(3) . . . . ? C17 C12 C13 C14 -1.4(5) . . . . ? O11 C12 C13 C14 176.5(3) . . . . ? C12 C13 C14 C15 0.4(7) . . . . ? C13 C14 C15 C16 1.0(7) . . . . ? C14 C15 C16 C17 -1.4(6) . . . . ? C13 C12 C17 C16 1.0(4) . . . . ? O11 C12 C17 C16 -176.8(3) . . . . ? C15 C16 C17 C12 0.5(5) . . . . ? O10 P9 O18 C19 -55.9(2) . . . . ? O11 P9 O18 C19 -178.10(17) . . . . ? N8 P9 O18 C19 72.36(19) . . . . ? P9 O18 C19 C20 97.2(3) . . . . ? P9 O18 C19 C24 -88.0(3) . . . . ? C24 C19 C20 C21 0.0(5) . . . . ? O18 C19 C20 C21 174.8(3) . . . . ? C19 C20 C21 C22 0.4(6) . . . . ? C20 C21 C22 C23 -0.5(7) . . . . ? C21 C22 C23 C24 0.1(7) . . . . ? C20 C19 C24 C23 -0.4(5) . . . . ? O18 C19 C24 C23 -175.1(3) . . . . ? C22 C23 C24 C19 0.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.440 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 894845'