# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_Greg1330f #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H30 N2 O P2 S' _chemical_formula_sum 'C31 H30 N2 O P2 S' _chemical_formula_weight 540.57 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3636(8) _cell_length_b 34.410(3) _cell_length_c 9.3807(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.124(2) _cell_angle_gamma 90.00 _cell_volume 2690.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 30.44 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9241 _exptl_absorpt_correction_T_max 0.9386 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27883 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6484 _reflns_number_gt 5501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0435P)^2^+1.4395P] 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 6484 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.44796(18) 0.37465(5) 0.70758(18) 0.0168(3) Uani 1 1 d . . . C2 C 0.27558(18) 0.34197(4) 0.48551(18) 0.0166(3) Uani 1 1 d . . . C3 C 0.21232(18) 0.37834(5) 0.47870(18) 0.0163(3) Uani 1 1 d . . . C4 C 0.2909(2) 0.43781(5) 0.66071(19) 0.0199(3) Uani 1 1 d . . . H4A H 0.1790 0.4451 0.5823 0.024 Uiso 1 1 calc R . . C5 C 0.4019(2) 0.46667(5) 0.6384(2) 0.0286(4) Uani 1 1 d . . . H5A H 0.5136 0.4601 0.7113 0.043 Uiso 1 1 calc R . . H5B H 0.3783 0.4930 0.6619 0.043 Uiso 1 1 calc R . . H5C H 0.3854 0.4655 0.5275 0.043 Uiso 1 1 calc R . . C6 C 0.2993(2) 0.44006(6) 0.8267(2) 0.0297(4) Uani 1 1 d . . . H6A H 0.2671 0.4661 0.8434 0.044 Uiso 1 1 calc R . . H6B H 0.4094 0.4349 0.9082 0.044 Uiso 1 1 calc R . . H6C H 0.2268 0.4207 0.8352 0.044 Uiso 1 1 calc R . . C7 C 0.5312(2) 0.30722(5) 0.6877(2) 0.0263(4) Uani 1 1 d . . . H7C H 0.4738 0.2829 0.6422 0.039 Uiso 1 1 calc R . . H7B H 0.5773 0.3063 0.8047 0.039 Uiso 1 1 calc R . . H7A H 0.6173 0.3106 0.6568 0.039 Uiso 1 1 calc R . . C8 C 0.17303(19) 0.31699(5) 0.15923(19) 0.0185(3) Uani 1 1 d . . . C9 C 0.2980(2) 0.33947(5) 0.1601(2) 0.0224(3) Uani 1 1 d . . . H9A H 0.3778 0.3498 0.2580 0.027 Uiso 1 1 calc R . . C10 C 0.3056(2) 0.34668(5) 0.0184(2) 0.0276(4) Uani 1 1 d . . . H10A H 0.3904 0.3619 0.0189 0.033 Uiso 1 1 calc R . . C11 C 0.1891(2) 0.33152(6) -0.1241(2) 0.0296(4) Uani 1 1 d . . . H11A H 0.1954 0.3361 -0.2210 0.036 Uiso 1 1 calc R . . C12 C 0.0636(2) 0.30977(6) -0.1267(2) 0.0278(4) Uani 1 1 d . . . H12A H -0.0175 0.3002 -0.2255 0.033 Uiso 1 1 calc R . . C13 C 0.0559(2) 0.30182(5) 0.0152(2) 0.0220(3) Uani 1 1 d . . . H13A H -0.0284 0.2862 0.0140 0.026 Uiso 1 1 calc R . . C14 C -0.01035(19) 0.29532(4) 0.33457(19) 0.0177(3) Uani 1 1 d . . . C15 C -0.1520(2) 0.31125(5) 0.2166(2) 0.0201(3) Uani 1 1 d . . . H15A H -0.1501 0.3260 0.1320 0.024 Uiso 1 1 calc R . . C16 C -0.2960(2) 0.30552(5) 0.2227(2) 0.0247(4) Uani 1 1 d . . . H16A H -0.3922 0.3165 0.1424 0.030 Uiso 1 1 calc R . . C17 C -0.2998(2) 0.28382(5) 0.3459(2) 0.0275(4) Uani 1 1 d . . . H17A H -0.3982 0.2803 0.3504 0.033 Uiso 1 1 calc R . . C18 C -0.1600(2) 0.26737(5) 0.4620(2) 0.0279(4) Uani 1 1 d . . . H18A H -0.1632 0.2522 0.5450 0.033 Uiso 1 1 calc R . . C19 C -0.0154(2) 0.27304(5) 0.4575(2) 0.0236(3) Uani 1 1 d . . . H19A H 0.0802 0.2618 0.5377 0.028 Uiso 1 1 calc R . . C20 C 0.08080(19) 0.44480(5) 0.26954(19) 0.0180(3) Uani 1 1 d . . . C21 C 0.1680(2) 0.44790(5) 0.1827(2) 0.0218(3) Uani 1 1 d . . . H21A H 0.1974 0.4251 0.1456 0.026 Uiso 1 1 calc R . . C22 C 0.2121(2) 0.48407(5) 0.1500(2) 0.0255(4) Uani 1 1 d . . . H22A H 0.2732 0.4858 0.0925 0.031 Uiso 1 1 calc R . . C23 C 0.1675(2) 0.51771(5) 0.2010(2) 0.0262(4) Uani 1 1 d . . . H23A H 0.1983 0.5424 0.1791 0.031 Uiso 1 1 calc R . . C24 C 0.0779(2) 0.51498(5) 0.2838(2) 0.0247(4) Uani 1 1 d . . . H24A H 0.0470 0.5379 0.3188 0.030 Uiso 1 1 calc R . . C25 C 0.03299(19) 0.47894(5) 0.3161(2) 0.0206(3) Uani 1 1 d . . . H25A H -0.0311 0.4775 0.3705 0.025 Uiso 1 1 calc R . . C26 C -0.11433(19) 0.40207(5) 0.38254(19) 0.0181(3) Uani 1 1 d . . . C27 C -0.0956(2) 0.38574(5) 0.5262(2) 0.0236(3) Uani 1 1 d . . . H27A H 0.0028 0.3735 0.5955 0.028 Uiso 1 1 calc R . . C28 C -0.2194(2) 0.38720(5) 0.5688(2) 0.0288(4) Uani 1 1 d . . . H28A H -0.2054 0.3760 0.6669 0.035 Uiso 1 1 calc R . . C29 C -0.3630(2) 0.40501(5) 0.4688(2) 0.0296(4) Uani 1 1 d . . . H29A H -0.4470 0.4064 0.4989 0.035 Uiso 1 1 calc R . . C30 C -0.3841(2) 0.42087(5) 0.3248(2) 0.0275(4) Uani 1 1 d . . . H30A H -0.4832 0.4328 0.2557 0.033 Uiso 1 1 calc R . . C31 C -0.26143(19) 0.41935(5) 0.2813(2) 0.0216(3) Uani 1 1 d . . . H31A H -0.2772 0.4301 0.1819 0.026 Uiso 1 1 calc R . . N1 N 0.31840(15) 0.39777(4) 0.61850(16) 0.0165(3) Uani 1 1 d . . . N2 N 0.41926(15) 0.33999(4) 0.62684(15) 0.0173(3) Uani 1 1 d . . . O1 O 0.28486(14) 0.26560(3) 0.40781(14) 0.0245(3) Uani 1 1 d . . . P1 P 0.18672(5) 0.301306(12) 0.34764(5) 0.01660(10) Uani 1 1 d . . . P2 P 0.03151(5) 0.395298(12) 0.30557(5) 0.01642(10) Uani 1 1 d . . . S1 S 0.61464(5) 0.385153(12) 0.87738(5) 0.02164(10) 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 0.0170(7) 0.0176(8) 0.0183(7) 0.0009(6) 0.0103(6) 0.0004(6) C2 0.0153(7) 0.0162(7) 0.0183(7) 0.0002(6) 0.0076(6) 0.0003(6) C3 0.0155(7) 0.0169(7) 0.0171(7) -0.0011(6) 0.0079(6) -0.0005(6) C4 0.0201(8) 0.0161(8) 0.0221(8) -0.0039(6) 0.0083(6) 0.0024(6) C5 0.0259(9) 0.0180(8) 0.0383(10) -0.0031(7) 0.0115(8) -0.0037(7) C6 0.0313(10) 0.0332(10) 0.0232(8) -0.0061(7) 0.0114(8) 0.0082(8) C7 0.0233(9) 0.0202(8) 0.0272(9) 0.0012(7) 0.0044(7) 0.0072(7) C8 0.0203(8) 0.0145(7) 0.0229(8) -0.0008(6) 0.0118(7) 0.0026(6) C9 0.0189(8) 0.0207(8) 0.0286(8) 0.0007(7) 0.0116(7) 0.0018(6) C10 0.0240(9) 0.0265(9) 0.0377(10) 0.0089(7) 0.0188(8) 0.0053(7) C11 0.0336(10) 0.0329(10) 0.0288(9) 0.0109(8) 0.0198(8) 0.0137(8) C12 0.0285(9) 0.0312(10) 0.0219(8) -0.0019(7) 0.0099(7) 0.0059(8) C13 0.0220(8) 0.0199(8) 0.0247(8) -0.0035(6) 0.0112(7) 0.0000(6) C14 0.0190(7) 0.0142(7) 0.0206(7) -0.0016(6) 0.0098(6) -0.0018(6) C15 0.0222(8) 0.0156(7) 0.0230(8) -0.0011(6) 0.0107(7) -0.0011(6) C16 0.0193(8) 0.0235(9) 0.0301(9) -0.0029(7) 0.0103(7) -0.0009(7) C17 0.0265(9) 0.0273(9) 0.0347(9) -0.0088(7) 0.0192(8) -0.0096(7) C18 0.0337(10) 0.0276(9) 0.0268(9) -0.0021(7) 0.0177(8) -0.0102(8) C19 0.0263(9) 0.0214(8) 0.0211(8) 0.0013(6) 0.0090(7) -0.0037(7) C20 0.0162(7) 0.0170(8) 0.0184(7) -0.0003(6) 0.0059(6) 0.0008(6) C21 0.0211(8) 0.0227(8) 0.0225(8) -0.0017(6) 0.0108(7) 0.0009(6) C22 0.0230(8) 0.0289(9) 0.0270(9) 0.0011(7) 0.0136(7) -0.0030(7) C23 0.0222(8) 0.0212(8) 0.0318(9) 0.0037(7) 0.0094(7) -0.0025(7) C24 0.0221(8) 0.0176(8) 0.0328(9) -0.0003(7) 0.0109(7) 0.0016(6) C25 0.0180(8) 0.0199(8) 0.0247(8) 0.0002(6) 0.0105(7) 0.0009(6) C26 0.0176(7) 0.0155(7) 0.0223(8) -0.0028(6) 0.0099(6) -0.0017(6) C27 0.0231(8) 0.0216(8) 0.0262(8) 0.0014(7) 0.0114(7) 0.0012(7) C28 0.0355(10) 0.0266(9) 0.0316(9) -0.0016(7) 0.0215(8) -0.0046(8) C29 0.0278(9) 0.0256(9) 0.0452(11) -0.0084(8) 0.0253(9) -0.0058(7) C30 0.0187(8) 0.0252(9) 0.0374(10) -0.0032(7) 0.0117(8) 0.0004(7) C31 0.0181(8) 0.0206(8) 0.0243(8) -0.0010(6) 0.0082(7) 0.0002(6) N1 0.0157(6) 0.0148(6) 0.0192(6) -0.0016(5) 0.0082(5) -0.0006(5) N2 0.0164(6) 0.0167(6) 0.0180(6) 0.0001(5) 0.0070(5) 0.0010(5) O1 0.0239(6) 0.0163(6) 0.0296(6) 0.0003(5) 0.0090(5) 0.0047(5) P1 0.01643(19) 0.01349(19) 0.01960(19) -0.00114(15) 0.00796(16) 0.00062(15) P2 0.01560(19) 0.01514(19) 0.01797(19) -0.00103(14) 0.00718(16) 0.00144(15) S1 0.0180(2) 0.0244(2) 0.01840(19) -0.00179(15) 0.00474(15) -0.00050(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 C1 N1 1.371(2) . ? C1 N2 1.372(2) . ? C1 S1 1.6844(16) . ? C2 C3 1.374(2) . ? C2 N2 1.3950(19) . ? C2 P1 1.8279(16) . ? C3 N1 1.4021(19) . ? C3 P2 1.8268(16) . ? C4 N1 1.488(2) . ? C4 C5 1.520(2) . ? C4 C6 1.525(2) . ? C4 H4A 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.466(2) . ? C7 H7C 0.9800 . ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C8 C13 1.396(2) . ? C8 C9 1.400(2) . ? C8 P1 1.7958(16) . ? C9 C10 1.386(2) . ? C9 H9A 0.9500 . ? C10 C11 1.386(3) . ? C10 H10A 0.9500 . ? C11 C12 1.384(3) . ? C11 H11A 0.9500 . ? C12 C13 1.393(2) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.395(2) . ? C14 C19 1.404(2) . ? C14 P1 1.8045(16) . ? C15 C16 1.389(2) . ? C15 H15A 0.9500 . ? C16 C17 1.389(3) . ? C16 H16A 0.9500 . ? C17 C18 1.386(3) . ? C17 H17A 0.9500 . ? C18 C19 1.387(2) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.396(2) . ? C20 C25 1.396(2) . ? C20 P2 1.8360(16) . ? C21 C22 1.389(2) . ? C21 H21A 0.9500 . ? C22 C23 1.387(3) . ? C22 H22A 0.9500 . ? C23 C24 1.382(3) . ? C23 H23A 0.9500 . ? C24 C25 1.387(2) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.395(2) . ? C26 C31 1.400(2) . ? C26 P2 1.8274(16) . ? C27 C28 1.389(2) . ? C27 H27A 0.9500 . ? C28 C29 1.383(3) . ? C28 H28A 0.9500 . ? C29 C30 1.385(3) . ? C29 H29A 0.9500 . ? C30 C31 1.385(2) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? O1 P1 1.4832(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 105.78(13) . . ? N1 C1 S1 129.26(12) . . ? N2 C1 S1 124.92(12) . . ? C3 C2 N2 107.29(13) . . ? C3 C2 P1 128.09(12) . . ? N2 C2 P1 124.45(11) . . ? C2 C3 N1 106.52(13) . . ? C2 C3 P2 122.52(12) . . ? N1 C3 P2 130.80(12) . . ? N1 C4 C5 110.87(13) . . ? N1 C4 C6 112.59(14) . . ? C5 C4 C6 112.80(15) . . ? N1 C4 H4A 106.7 . . ? C5 C4 H4A 106.7 . . ? C6 C4 H4A 106.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7C 109.5 . . ? N2 C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? N2 C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? C13 C8 C9 119.88(15) . . ? C13 C8 P1 120.79(12) . . ? C9 C8 P1 118.42(13) . . ? C10 C9 C8 120.12(16) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C11 C10 C9 119.73(17) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C12 C11 C10 120.61(16) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 120.22(17) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C8 119.41(16) . . ? C12 C13 H13A 120.3 . . ? C8 C13 H13A 120.3 . . ? C15 C14 C19 119.35(15) . . ? C15 C14 P1 125.61(12) . . ? C19 C14 P1 115.03(12) . . ? C16 C15 C14 120.09(15) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C17 120.24(17) . . ? C15 C16 H16A 119.9 . . ? C17 C16 H16A 119.9 . . ? C18 C17 C16 120.01(16) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 120.26(16) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C18 C19 C14 120.04(16) . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? C21 C20 C25 118.34(15) . . ? C21 C20 P2 116.19(12) . . ? C25 C20 P2 125.43(12) . . ? C22 C21 C20 120.60(16) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C23 C22 C21 120.36(16) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? C24 C23 C22 119.46(16) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C23 C24 C25 120.41(16) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C24 C25 C20 120.76(15) . . ? C24 C25 H25A 119.6 . . ? C20 C25 H25A 119.6 . . ? C27 C26 C31 118.56(15) . . ? C27 C26 P2 122.86(13) . . ? C31 C26 P2 117.85(12) . . ? C28 C27 C26 120.64(17) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C29 C28 C27 120.09(17) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 119.91(16) . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C29 C30 C31 120.27(17) . . ? C29 C30 H30A 119.9 . . ? C31 C30 H30A 119.9 . . ? C30 C31 C26 120.51(16) . . ? C30 C31 H31A 119.7 . . ? C26 C31 H31A 119.7 . . ? C1 N1 C3 110.25(13) . . ? C1 N1 C4 125.99(13) . . ? C3 N1 C4 123.76(13) . . ? C1 N2 C2 110.09(13) . . ? C1 N2 C7 121.89(13) . . ? C2 N2 C7 128.02(14) . . ? O1 P1 C8 112.17(7) . . ? O1 P1 C14 111.61(7) . . ? C8 P1 C14 110.83(7) . . ? O1 P1 C2 111.20(7) . . ? C8 P1 C2 105.75(7) . . ? C14 P1 C2 104.89(7) . . ? C3 P2 C26 104.25(7) . . ? C3 P2 C20 104.54(7) . . ? C26 P2 C20 104.49(7) . . ? 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 N2 C2 C3 N1 -0.92(16) . . . . ? P1 C2 C3 N1 174.63(11) . . . . ? N2 C2 C3 P2 175.01(10) . . . . ? P1 C2 C3 P2 -9.4(2) . . . . ? C13 C8 C9 C10 0.0(2) . . . . ? P1 C8 C9 C10 169.23(13) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? C10 C11 C12 C13 -2.1(3) . . . . ? C11 C12 C13 C8 2.0(3) . . . . ? C9 C8 C13 C12 -1.0(2) . . . . ? P1 C8 C13 C12 -169.92(13) . . . . ? C19 C14 C15 C16 1.0(2) . . . . ? P1 C14 C15 C16 -177.91(13) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 -0.7(2) . . . . ? P1 C14 C19 C18 178.31(13) . . . . ? C25 C20 C21 C22 2.9(2) . . . . ? P2 C20 C21 C22 -179.57(13) . . . . ? C20 C21 C22 C23 -1.2(3) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C23 C24 C25 C20 1.7(3) . . . . ? C21 C20 C25 C24 -3.2(2) . . . . ? P2 C20 C25 C24 179.54(13) . . . . ? C31 C26 C27 C28 -1.1(3) . . . . ? P2 C26 C27 C28 -171.10(14) . . . . ? C26 C27 C28 C29 -0.1(3) . . . . ? C27 C28 C29 C30 1.0(3) . . . . ? C28 C29 C30 C31 -0.7(3) . . . . ? C29 C30 C31 C26 -0.5(3) . . . . ? C27 C26 C31 C30 1.4(2) . . . . ? P2 C26 C31 C30 171.91(13) . . . . ? N2 C1 N1 C3 -2.69(16) . . . . ? S1 C1 N1 C3 175.12(12) . . . . ? N2 C1 N1 C4 177.36(13) . . . . ? S1 C1 N1 C4 -4.8(2) . . . . ? C2 C3 N1 C1 2.28(17) . . . . ? P2 C3 N1 C1 -173.19(12) . . . . ? C2 C3 N1 C4 -177.77(13) . . . . ? P2 C3 N1 C4 6.8(2) . . . . ? C5 C4 N1 C1 73.33(19) . . . . ? C6 C4 N1 C1 -54.1(2) . . . . ? C5 C4 N1 C3 -106.62(17) . . . . ? C6 C4 N1 C3 125.95(16) . . . . ? N1 C1 N2 C2 2.10(16) . . . . ? S1 C1 N2 C2 -175.83(11) . . . . ? N1 C1 N2 C7 -178.76(14) . . . . ? S1 C1 N2 C7 3.3(2) . . . . ? C3 C2 N2 C1 -0.73(17) . . . . ? P1 C2 N2 C1 -176.48(11) . . . . ? C3 C2 N2 C7 -179.81(15) . . . . ? P1 C2 N2 C7 4.4(2) . . . . ? C13 C8 P1 O1 85.86(14) . . . . ? C9 C8 P1 O1 -83.26(14) . . . . ? C13 C8 P1 C14 -39.63(15) . . . . ? C9 C8 P1 C14 151.25(13) . . . . ? C13 C8 P1 C2 -152.76(13) . . . . ? C9 C8 P1 C2 38.12(15) . . . . ? C15 C14 P1 O1 -144.20(14) . . . . ? C19 C14 P1 O1 36.88(15) . . . . ? C15 C14 P1 C8 -18.40(17) . . . . ? C19 C14 P1 C8 162.68(12) . . . . ? C15 C14 P1 C2 95.28(15) . . . . ? C19 C14 P1 C2 -83.64(13) . . . . ? C3 C2 P1 O1 -173.24(14) . . . . ? N2 C2 P1 O1 1.61(15) . . . . ? C3 C2 P1 C8 64.76(16) . . . . ? N2 C2 P1 C8 -120.40(13) . . . . ? C3 C2 P1 C14 -52.45(16) . . . . ? N2 C2 P1 C14 122.40(13) . . . . ? C2 C3 P2 C26 115.32(14) . . . . ? N1 C3 P2 C26 -69.84(15) . . . . ? C2 C3 P2 C20 -135.25(13) . . . . ? N1 C3 P2 C20 39.59(16) . . . . ? C27 C26 P2 C3 -17.07(16) . . . . ? C31 C26 P2 C3 172.83(13) . . . . ? C27 C26 P2 C20 -126.53(14) . . . . ? C31 C26 P2 C20 63.37(14) . . . . ? C21 C20 P2 C3 82.11(13) . . . . ? C25 C20 P2 C3 -100.56(15) . . . . ? C21 C20 P2 C26 -168.64(12) . . . . ? C25 C20 P2 C26 8.69(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.434 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 888238' ####################################################################### # # 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_Greg1608f #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H32 N2 O2 P2 S' _chemical_formula_sum 'C32 H32 N2 O2 P2 S' _chemical_formula_weight 570.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 11.6761(9) _cell_length_b 11.7150(11) _cell_length_c 12.7206(13) _cell_angle_alpha 104.978(4) _cell_angle_beta 104.629(3) _cell_angle_gamma 111.483(3) _cell_volume 1442.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2486 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9798 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'SADABS (2009/2), Bruker AXS 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8-KappaApexII' _diffrn_measurement_method '\f and \w CCD rotation images, thin slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12940 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5525 _reflns_number_gt 3939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0485P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5525 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C 0.1321(2) 0.6645(2) 0.3728(2) 0.0166(5) Uani 1 1 d . . . C2 C 0.0106(2) 0.7320(2) 0.2573(2) 0.0153(5) Uani 1 1 d . . . C3 C 0.1418(2) 0.8063(2) 0.2789(2) 0.0156(5) Uani 1 1 d . . . C4 C -0.1118(2) 0.5349(2) 0.3094(2) 0.0199(6) Uani 1 1 d . . . H4A H -0.1793 0.5653 0.3165 0.024 Uiso 1 1 calc R . . H4B H -0.0862 0.5090 0.3765 0.024 Uiso 1 1 calc R . . C5 C -0.1722(3) 0.4149(2) 0.1947(2) 0.0215(6) Uani 1 1 d . . . H5A H -0.1019 0.3908 0.1838 0.026 Uiso 1 1 calc R . . H5B H -0.2062 0.4386 0.1283 0.026 Uiso 1 1 calc R . . C6 C -0.2863(3) 0.2944(3) 0.1918(3) 0.0235(6) Uani 1 1 d . . . H6A H -0.3151 0.2166 0.1192 0.028 Uiso 1 1 calc R . . H6B H -0.2530 0.2733 0.2602 0.028 Uiso 1 1 calc R . . C7 C -0.4060(3) 0.3164(3) 0.1951(3) 0.0309(7) Uani 1 1 d . . . H7A H -0.3842 0.3783 0.2741 0.046 Uiso 1 1 calc R . . H7B H -0.4821 0.2312 0.1759 0.046 Uiso 1 1 calc R . . H7C H -0.4291 0.3539 0.1372 0.046 Uiso 1 1 calc R . . C8 C 0.3597(2) 0.8164(3) 0.4019(2) 0.0217(6) Uani 1 1 d . . . H8A H 0.3826 0.7818 0.4622 0.033 Uiso 1 1 calc R . . H8B H 0.4025 0.9139 0.4380 0.033 Uiso 1 1 calc R . . H8C H 0.3911 0.7882 0.3401 0.033 Uiso 1 1 calc R . . C9 C -0.2027(2) 0.6508(2) 0.0299(2) 0.0175(5) Uani 1 1 d . . . C10 C -0.3419(3) 0.5857(3) -0.0277(3) 0.0281(7) Uani 1 1 d . . . H10 H -0.3953 0.5956 0.0158 0.034 Uiso 1 1 calc R . . C11 C -0.4023(3) 0.5075(3) -0.1465(3) 0.0330(7) Uani 1 1 d . . . H11 H -0.4968 0.4625 -0.1844 0.040 Uiso 1 1 calc R . . C12 C -0.3248(3) 0.4947(2) -0.2107(2) 0.0267(6) Uani 1 1 d . . . H12 H -0.3659 0.4425 -0.2931 0.032 Uiso 1 1 calc R . . C13 C -0.1882(3) 0.5578(3) -0.1549(3) 0.0348(7) Uani 1 1 d . . . H13 H -0.1354 0.5484 -0.1991 0.042 Uiso 1 1 calc R . . C14 C -0.1268(3) 0.6350(3) -0.0351(3) 0.0316(7) Uani 1 1 d . . . H14 H -0.0323 0.6772 0.0025 0.038 Uiso 1 1 calc R . . C15 C -0.0910(2) 0.9177(2) 0.2190(2) 0.0160(5) Uani 1 1 d . . . C16 C -0.0556(2) 0.9965(3) 0.3362(2) 0.0208(6) Uani 1 1 d . . . H16 H -0.0514 0.9586 0.3938 0.025 Uiso 1 1 calc R . . C17 C -0.0266(3) 1.1293(3) 0.3696(2) 0.0251(6) Uani 1 1 d . . . H17 H -0.0018 1.1828 0.4497 0.030 Uiso 1 1 calc R . . C18 C -0.0343(3) 1.1832(3) 0.2839(3) 0.0270(7) Uani 1 1 d . . . H18 H -0.0140 1.2744 0.3060 0.032 Uiso 1 1 calc R . . C19 C -0.0711(3) 1.1055(3) 0.1674(2) 0.0244(6) Uani 1 1 d . . . H19 H -0.0771 1.1431 0.1096 0.029 Uiso 1 1 calc R . . C20 C -0.0995(2) 0.9726(3) 0.1345(2) 0.0200(6) Uani 1 1 d . . . H20 H -0.1247 0.9192 0.0543 0.024 Uiso 1 1 calc R . . C21 C 0.2649(2) 1.0907(2) 0.3446(2) 0.0173(5) Uani 1 1 d . . . C22 C 0.2842(2) 1.1009(2) 0.4599(2) 0.0193(6) Uani 1 1 d . . . H22 H 0.2691 1.0241 0.4777 0.023 Uiso 1 1 calc R . . C23 C 0.3252(3) 1.2217(3) 0.5488(2) 0.0234(6) Uani 1 1 d . . . H23 H 0.3386 1.2279 0.6274 0.028 Uiso 1 1 calc R . . C24 C 0.3465(3) 1.3338(3) 0.5224(3) 0.0291(7) Uani 1 1 d . . . H24 H 0.3741 1.4169 0.5829 0.035 Uiso 1 1 calc R . . C25 C 0.3275(3) 1.3245(3) 0.4085(3) 0.0325(7) Uani 1 1 d . . . H25 H 0.3428 1.4017 0.3911 0.039 Uiso 1 1 calc R . . C26 C 0.2863(3) 1.2035(3) 0.3186(2) 0.0246(6) Uani 1 1 d . . . H26 H 0.2729 1.1977 0.2402 0.030 Uiso 1 1 calc R . . C27 C 0.3598(2) 0.9299(3) 0.2133(2) 0.0181(6) Uani 1 1 d . . . C28 C 0.3443(3) 0.8145(3) 0.1325(2) 0.0269(6) Uani 1 1 d . . . H28 H 0.2574 0.7443 0.0827 0.032 Uiso 1 1 calc R . . C29 C 0.4553(3) 0.8014(3) 0.1243(3) 0.0365(8) Uani 1 1 d . . . H29 H 0.4451 0.7223 0.0695 0.044 Uiso 1 1 calc R . . C30 C 0.5814(3) 0.9052(4) 0.1971(3) 0.0407(8) Uani 1 1 d . . . H30 H 0.6578 0.8961 0.1928 0.049 Uiso 1 1 calc R . . C31 C 0.5976(3) 1.0211(3) 0.2753(3) 0.0329(7) Uani 1 1 d . . . H31 H 0.6846 1.0919 0.3239 0.039 Uiso 1 1 calc R . . C32 C 0.4871(2) 1.0343(3) 0.2833(2) 0.0239(6) Uani 1 1 d . . . H32 H 0.4979 1.1148 0.3365 0.029 Uiso 1 1 calc R . . N1 N 0.0061(2) 0.64458(19) 0.31527(18) 0.0165(5) Uani 1 1 d . . . N2 N 0.21511(19) 0.76445(19) 0.35009(18) 0.0159(5) Uani 1 1 d . . . O1 O -0.24206(16) 0.68916(17) 0.23432(16) 0.0222(4) Uani 1 1 d . . . O2 O 0.11439(17) 0.91053(17) 0.11162(15) 0.0195(4) Uani 1 1 d . . . P1 P -0.14004(6) 0.74338(6) 0.18638(6) 0.01617(16) Uani 1 1 d . . . P2 P 0.21166(6) 0.93578(6) 0.22563(6) 0.01463(16) Uani 1 1 d . . . S S 0.17697(7) 0.58380(7) 0.45346(6) 0.02325(17) 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 0.0166(14) 0.0154(13) 0.0167(13) 0.0038(11) 0.0073(11) 0.0072(11) C2 0.0136(13) 0.0168(13) 0.0139(13) 0.0040(11) 0.0057(10) 0.0067(11) C3 0.0167(14) 0.0145(13) 0.0153(13) 0.0043(11) 0.0065(11) 0.0077(11) C4 0.0175(14) 0.0215(14) 0.0235(15) 0.0123(12) 0.0127(12) 0.0063(12) C5 0.0194(15) 0.0206(14) 0.0267(15) 0.0107(12) 0.0111(12) 0.0090(12) C6 0.0182(14) 0.0189(14) 0.0309(16) 0.0097(12) 0.0089(12) 0.0064(12) C7 0.0231(16) 0.0269(16) 0.0426(19) 0.0141(14) 0.0157(14) 0.0091(13) C8 0.0142(14) 0.0217(14) 0.0252(15) 0.0104(12) 0.0037(11) 0.0061(12) C9 0.0188(14) 0.0139(13) 0.0189(14) 0.0054(11) 0.0067(11) 0.0076(11) C10 0.0191(15) 0.0307(16) 0.0298(17) 0.0033(13) 0.0053(13) 0.0155(13) C11 0.0206(16) 0.0279(16) 0.0324(18) -0.0023(14) -0.0041(13) 0.0122(13) C12 0.0339(17) 0.0176(14) 0.0169(15) 0.0017(12) 0.0021(13) 0.0087(13) C13 0.0334(18) 0.0322(17) 0.0229(17) -0.0010(13) 0.0148(14) 0.0044(14) C14 0.0179(15) 0.0329(17) 0.0251(16) -0.0013(13) 0.0078(13) 0.0014(13) C15 0.0081(13) 0.0220(14) 0.0183(14) 0.0051(11) 0.0055(11) 0.0089(11) C16 0.0166(14) 0.0258(14) 0.0207(15) 0.0073(12) 0.0064(11) 0.0122(12) C17 0.0204(15) 0.0289(15) 0.0229(15) 0.0021(13) 0.0070(12) 0.0147(13) C18 0.0213(15) 0.0220(15) 0.0409(18) 0.0113(14) 0.0114(13) 0.0141(12) C19 0.0214(15) 0.0277(15) 0.0283(16) 0.0135(13) 0.0095(13) 0.0140(13) C20 0.0124(13) 0.0262(14) 0.0214(15) 0.0070(12) 0.0066(11) 0.0103(11) C21 0.0138(13) 0.0174(13) 0.0199(14) 0.0053(11) 0.0071(11) 0.0074(11) C22 0.0169(14) 0.0202(14) 0.0218(15) 0.0073(12) 0.0090(12) 0.0091(11) C23 0.0178(15) 0.0279(15) 0.0197(15) 0.0032(12) 0.0070(12) 0.0101(12) C24 0.0261(16) 0.0221(15) 0.0309(17) 0.0000(13) 0.0071(13) 0.0125(13) C25 0.0378(18) 0.0180(15) 0.0380(19) 0.0100(14) 0.0117(15) 0.0118(14) C26 0.0283(16) 0.0210(14) 0.0240(16) 0.0101(12) 0.0094(13) 0.0105(12) C27 0.0165(14) 0.0260(14) 0.0209(14) 0.0138(12) 0.0123(11) 0.0125(12) C28 0.0293(16) 0.0312(16) 0.0252(16) 0.0096(13) 0.0140(13) 0.0176(14) C29 0.044(2) 0.055(2) 0.0343(18) 0.0211(16) 0.0250(16) 0.0386(18) C30 0.0335(19) 0.069(2) 0.055(2) 0.043(2) 0.0319(18) 0.0367(19) C31 0.0204(16) 0.0437(19) 0.048(2) 0.0325(17) 0.0176(15) 0.0156(14) C32 0.0175(15) 0.0278(15) 0.0322(17) 0.0193(13) 0.0113(13) 0.0099(12) N1 0.0179(12) 0.0153(11) 0.0160(11) 0.0065(9) 0.0084(9) 0.0058(9) N2 0.0124(11) 0.0171(11) 0.0170(11) 0.0059(9) 0.0050(9) 0.0066(9) O1 0.0144(9) 0.0275(10) 0.0273(11) 0.0107(9) 0.0137(8) 0.0086(8) O2 0.0187(10) 0.0235(10) 0.0177(10) 0.0077(8) 0.0080(8) 0.0109(8) P1 0.0119(3) 0.0182(3) 0.0171(4) 0.0046(3) 0.0067(3) 0.0065(3) P2 0.0134(3) 0.0160(3) 0.0159(4) 0.0061(3) 0.0075(3) 0.0072(3) S 0.0257(4) 0.0238(4) 0.0243(4) 0.0138(3) 0.0100(3) 0.0122(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.367(3) . ? C1 N2 1.371(3) . ? C1 S 1.678(2) . ? C2 C3 1.367(3) . ? C2 N1 1.401(3) . ? C2 P1 1.832(2) . ? C3 N2 1.393(3) . ? C3 P2 1.825(2) . ? C4 N1 1.469(3) . ? C4 C5 1.515(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N2 1.461(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.384(4) . ? C9 C10 1.401(3) . ? C9 P1 1.801(3) . ? C10 C11 1.376(4) . ? C10 H10 0.9500 . ? C11 C12 1.385(4) . ? C11 H11 0.9500 . ? C12 C13 1.373(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.389(3) . ? C15 C16 1.394(3) . ? C15 P1 1.805(2) . ? C16 C17 1.383(3) . ? C16 H16 0.9500 . ? C17 C18 1.394(4) . ? C17 H17 0.9500 . ? C18 C19 1.380(4) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.391(3) . ? C21 C26 1.395(3) . ? C21 P2 1.803(3) . ? C22 C23 1.384(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(4) . ? C23 H23 0.9500 . ? C24 C25 1.379(4) . ? C24 H24 0.9500 . ? C25 C26 1.390(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.387(4) . ? C27 C32 1.391(4) . ? C27 P2 1.800(2) . ? C28 C29 1.385(4) . ? C28 H28 0.9500 . ? C29 C30 1.387(5) . ? C29 H29 0.9500 . ? C30 C31 1.374(4) . ? C30 H30 0.9500 . ? C31 C32 1.379(4) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? O1 P1 1.4857(17) . ? O2 P2 1.4768(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 105.42(19) . . ? N1 C1 S 127.74(18) . . ? N2 C1 S 126.84(19) . . ? C3 C2 N1 106.8(2) . . ? C3 C2 P1 131.95(18) . . ? N1 C2 P1 120.85(17) . . ? C2 C3 N2 107.0(2) . . ? C2 C3 P2 127.71(18) . . ? N2 C3 P2 125.30(18) . . ? N1 C4 C5 111.4(2) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 112.4(2) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 113.3(2) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 118.7(2) . . ? C14 C9 P1 126.1(2) . . ? C10 C9 P1 115.19(19) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.8(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 119.8(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.8(3) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 120.1(3) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C20 C15 C16 119.6(2) . . ? C20 C15 P1 124.3(2) . . ? C16 C15 P1 115.77(19) . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 119.9(2) . . ? C19 C20 H20 120.0 . . ? C15 C20 H20 120.0 . . ? C22 C21 C26 119.5(2) . . ? C22 C21 P2 122.53(19) . . ? C26 C21 P2 118.00(19) . . ? C23 C22 C21 120.8(2) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 119.5(3) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 120.1(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.7(3) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 119.4(3) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? C28 C27 C32 119.8(2) . . ? C28 C27 P2 117.7(2) . . ? C32 C27 P2 122.5(2) . . ? C29 C28 C27 120.2(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 119.2(3) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C31 C30 C29 121.0(3) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 119.8(3) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C31 C32 C27 120.0(3) . . ? C31 C32 H32 120.0 . . ? C27 C32 H32 120.0 . . ? C1 N1 C2 110.30(19) . . ? C1 N1 C4 121.20(19) . . ? C2 N1 C4 128.2(2) . . ? C1 N2 C3 110.5(2) . . ? C1 N2 C8 120.8(2) . . ? C3 N2 C8 128.6(2) . . ? O1 P1 C9 110.56(11) . . ? O1 P1 C15 110.04(10) . . ? C9 P1 C15 110.81(11) . . ? O1 P1 C2 110.16(11) . . ? C9 P1 C2 108.38(11) . . ? C15 P1 C2 106.81(11) . . ? O2 P2 C27 112.27(11) . . ? O2 P2 C21 115.79(11) . . ? C27 P2 C21 107.16(12) . . ? O2 P2 C3 110.58(11) . . ? C27 P2 C3 105.00(11) . . ? C21 P2 C3 105.27(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.6(3) . . . . ? P1 C2 C3 N2 171.80(19) . . . . ? N1 C2 C3 P2 179.11(18) . . . . ? P1 C2 C3 P2 -8.5(4) . . . . ? N1 C4 C5 C6 174.1(2) . . . . ? C4 C5 C6 C7 64.9(3) . . . . ? C14 C9 C10 C11 0.0(4) . . . . ? P1 C9 C10 C11 -177.5(2) . . . . ? C9 C10 C11 C12 -1.1(4) . . . . ? C10 C11 C12 C13 1.4(4) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C9 -0.8(5) . . . . ? C10 C9 C14 C13 1.0(4) . . . . ? P1 C9 C14 C13 178.2(2) . . . . ? C20 C15 C16 C17 -1.2(4) . . . . ? P1 C15 C16 C17 -174.85(19) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? C17 C18 C19 C20 -0.7(4) . . . . ? C18 C19 C20 C15 0.1(4) . . . . ? C16 C15 C20 C19 0.8(3) . . . . ? P1 C15 C20 C19 173.94(18) . . . . ? C26 C21 C22 C23 -0.4(4) . . . . ? P2 C21 C22 C23 -179.98(19) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 -0.3(4) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C24 C25 C26 C21 -0.4(4) . . . . ? C22 C21 C26 C25 0.4(4) . . . . ? P2 C21 C26 C25 -180.0(2) . . . . ? C32 C27 C28 C29 2.2(4) . . . . ? P2 C27 C28 C29 -176.2(2) . . . . ? C27 C28 C29 C30 -0.4(4) . . . . ? C28 C29 C30 C31 -1.1(5) . . . . ? C29 C30 C31 C32 0.9(4) . . . . ? C30 C31 C32 C27 0.9(4) . . . . ? C28 C27 C32 C31 -2.4(4) . . . . ? P2 C27 C32 C31 175.86(19) . . . . ? N2 C1 N1 C2 -0.2(3) . . . . ? S C1 N1 C2 -179.77(19) . . . . ? N2 C1 N1 C4 173.8(2) . . . . ? S C1 N1 C4 -5.7(3) . . . . ? C3 C2 N1 C1 0.5(3) . . . . ? P1 C2 N1 C1 -172.88(17) . . . . ? C3 C2 N1 C4 -173.0(2) . . . . ? P1 C2 N1 C4 13.6(3) . . . . ? C5 C4 N1 C1 -96.9(3) . . . . ? C5 C4 N1 C2 76.0(3) . . . . ? N1 C1 N2 C3 -0.1(3) . . . . ? S C1 N2 C3 179.39(18) . . . . ? N1 C1 N2 C8 177.6(2) . . . . ? S C1 N2 C8 -2.9(3) . . . . ? C2 C3 N2 C1 0.5(3) . . . . ? P2 C3 N2 C1 -179.25(17) . . . . ? C2 C3 N2 C8 -177.1(2) . . . . ? P2 C3 N2 C8 3.2(4) . . . . ? C14 C9 P1 O1 -152.8(2) . . . . ? C10 C9 P1 O1 24.5(2) . . . . ? C14 C9 P1 C15 84.9(2) . . . . ? C10 C9 P1 C15 -97.8(2) . . . . ? C14 C9 P1 C2 -32.0(3) . . . . ? C10 C9 P1 C2 145.32(19) . . . . ? C20 C15 P1 O1 -123.2(2) . . . . ? C16 C15 P1 O1 50.2(2) . . . . ? C20 C15 P1 C9 -0.6(2) . . . . ? C16 C15 P1 C9 172.77(18) . . . . ? C20 C15 P1 C2 117.3(2) . . . . ? C16 C15 P1 C2 -69.4(2) . . . . ? C3 C2 P1 O1 -152.1(2) . . . . ? N1 C2 P1 O1 19.4(2) . . . . ? C3 C2 P1 C9 86.8(3) . . . . ? N1 C2 P1 C9 -101.7(2) . . . . ? C3 C2 P1 C15 -32.6(3) . . . . ? N1 C2 P1 C15 138.90(19) . . . . ? C28 C27 P2 O2 -56.4(2) . . . . ? C32 C27 P2 O2 125.3(2) . . . . ? C28 C27 P2 C21 175.4(2) . . . . ? C32 C27 P2 C21 -3.0(2) . . . . ? C28 C27 P2 C3 63.8(2) . . . . ? C32 C27 P2 C3 -114.5(2) . . . . ? C22 C21 P2 O2 140.4(2) . . . . ? C26 C21 P2 O2 -39.2(2) . . . . ? C22 C21 P2 C27 -93.4(2) . . . . ? C26 C21 P2 C27 87.0(2) . . . . ? C22 C21 P2 C3 18.0(2) . . . . ? C26 C21 P2 C3 -161.61(19) . . . . ? C2 C3 P2 O2 -28.5(3) . . . . ? N2 C3 P2 O2 151.12(19) . . . . ? C2 C3 P2 C27 -149.8(2) . . . . ? N2 C3 P2 C27 29.8(2) . . . . ? C2 C3 P2 C21 97.2(2) . . . . ? N2 C3 P2 C21 -83.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.397 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 888239' ####################################################################### # # 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_Greg1148f #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H30 N2 O P2 S2' _chemical_formula_sum 'C39 H30 N2 O P2 S2' _chemical_formula_weight 668.71 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 Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 12.4616(3) _cell_length_b 20.6622(6) _cell_length_c 12.8212(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3301.26(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6330 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 29.76 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9119 _exptl_absorpt_correction_T_max 0.9545 _exptl_absorpt_process_details 'SADABS (2009/2), Bruker AXS 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8-KappaApexII' _diffrn_measurement_method '\f and \w CCD rotation images, thin slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17943 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7777 _reflns_number_gt 7142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0521P)^2^+0.6777P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(6) _refine_ls_number_reflns 7777 _refine_ls_number_parameters 416 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.006 _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 C1 C 0.67715(18) 0.42661(11) 0.63190(19) 0.0154(4) Uani 1 1 d . . . C2 C 0.78827(17) 0.48737(11) 0.52909(19) 0.0148(4) Uani 1 1 d . . . C3 C 0.72776(16) 0.52969(10) 0.5873(2) 0.0150(4) Uani 1 1 d . . . C4 C 0.60713(19) 0.51408(11) 0.7445(2) 0.0184(5) Uani 1 1 d . . . C5 C 0.4962(2) 0.50922(12) 0.7514(2) 0.0235(6) Uani 1 1 d . . . H5A H 0.4555 0.4899 0.6970 0.028 Uiso 1 1 calc R . . C6 C 0.4468(2) 0.53338(13) 0.8402(3) 0.0315(7) Uani 1 1 d . . . H6A H 0.3710 0.5307 0.8466 0.038 Uiso 1 1 calc R . . C7 C 0.5055(3) 0.56117(13) 0.9190(3) 0.0353(7) Uani 1 1 d . . . H7A H 0.4701 0.5789 0.9780 0.042 Uiso 1 1 calc R . . C8 C 0.6158(3) 0.56333(13) 0.9125(2) 0.0321(7) Uani 1 1 d . . . H8A H 0.6564 0.5807 0.9686 0.039 Uiso 1 1 calc R . . C9 C 0.6682(2) 0.54009(13) 0.8239(2) 0.0234(5) Uani 1 1 d . . . H9A H 0.7442 0.5421 0.8183 0.028 Uiso 1 1 calc R . . C10 C 0.79506(18) 0.36371(11) 0.5167(2) 0.0171(5) Uani 1 1 d . . . C11 C 0.86114(18) 0.32661(11) 0.5802(2) 0.0204(5) Uani 1 1 d . . . H11A H 0.8775 0.3405 0.6490 0.024 Uiso 1 1 calc R . . C12 C 0.9032(2) 0.26883(12) 0.5421(2) 0.0240(5) Uani 1 1 d . . . H12A H 0.9494 0.2434 0.5845 0.029 Uiso 1 1 calc R . . C13 C 0.8776(2) 0.24848(12) 0.4426(2) 0.0258(6) Uani 1 1 d . . . H13A H 0.9073 0.2094 0.4162 0.031 Uiso 1 1 calc R . . C14 C 0.8084(2) 0.28505(12) 0.3808(2) 0.0231(5) Uani 1 1 d . . . H14A H 0.7898 0.2702 0.3131 0.028 Uiso 1 1 calc R . . C15 C 0.76631(19) 0.34310(12) 0.4174(2) 0.0202(5) Uani 1 1 d . . . H15A H 0.7190 0.3681 0.3755 0.024 Uiso 1 1 calc R . . C16 C 0.96102(18) 0.57436(12) 0.4633(2) 0.0195(5) Uani 1 1 d . . . C17 C 0.97862(19) 0.59449(13) 0.5659(2) 0.0223(5) Uani 1 1 d . . . H17A H 0.9500 0.5703 0.6224 0.027 Uiso 1 1 calc R . . C18 C 1.0386(2) 0.65046(14) 0.5847(3) 0.0297(6) Uani 1 1 d . . . H18A H 1.0494 0.6650 0.6541 0.036 Uiso 1 1 calc R . . C19 C 1.0820(2) 0.68460(15) 0.5022(3) 0.0348(7) Uani 1 1 d . . . H19A H 1.1233 0.7224 0.5151 0.042 Uiso 1 1 calc R . . C20 C 1.0658(2) 0.66388(14) 0.4009(3) 0.0350(7) Uani 1 1 d . . . H20A H 1.0966 0.6873 0.3447 0.042 Uiso 1 1 calc R . . C21 C 1.0047(2) 0.60903(13) 0.3806(2) 0.0266(6) Uani 1 1 d . . . H21A H 0.9929 0.5953 0.3108 0.032 Uiso 1 1 calc R . . C22 C 0.99590(18) 0.43935(12) 0.4672(2) 0.0196(5) Uani 1 1 d . . . C23 C 1.04066(19) 0.43803(13) 0.5662(2) 0.0259(6) Uani 1 1 d . . . H23A H 1.0181 0.4685 0.6172 0.031 Uiso 1 1 calc R . . C24 C 1.1181(2) 0.39256(15) 0.5909(3) 0.0333(6) Uani 1 1 d . . . H24A H 1.1470 0.3911 0.6594 0.040 Uiso 1 1 calc R . . C25 C 1.1536(2) 0.34902(16) 0.5157(3) 0.0353(7) Uani 1 1 d . . . H25A H 1.2067 0.3178 0.5328 0.042 Uiso 1 1 calc R . . C26 C 1.1113(2) 0.35133(14) 0.4161(3) 0.0329(7) Uani 1 1 d . . . H26A H 1.1365 0.3221 0.3643 0.039 Uiso 1 1 calc R . . C27 C 1.0323(2) 0.39615(13) 0.3914(2) 0.0252(5) Uani 1 1 d . . . H27A H 1.0031 0.3974 0.3230 0.030 Uiso 1 1 calc R . . C28 C 0.73814(19) 0.65013(11) 0.4634(2) 0.0177(5) Uani 1 1 d . . . C29 C 0.80295(18) 0.70566(11) 0.4604(2) 0.0200(5) Uani 1 1 d . . . H29A H 0.8382 0.7202 0.5219 0.024 Uiso 1 1 calc R . . C30 C 0.8154(2) 0.73934(12) 0.3675(2) 0.0238(5) Uani 1 1 d . . . H30A H 0.8603 0.7765 0.3653 0.029 Uiso 1 1 calc R . . C31 C 0.7628(2) 0.71914(12) 0.2780(2) 0.0235(5) Uani 1 1 d . . . H31A H 0.7707 0.7427 0.2149 0.028 Uiso 1 1 calc R . . C32 C 0.6983(2) 0.66428(12) 0.2808(2) 0.0232(5) Uani 1 1 d . . . H32A H 0.6624 0.6504 0.2194 0.028 Uiso 1 1 calc R . . C33 C 0.6861(2) 0.62993(12) 0.3723(2) 0.0230(5) Uani 1 1 d . . . H33A H 0.6422 0.5924 0.3735 0.028 Uiso 1 1 calc R . . C34 C 0.56621(19) 0.62901(11) 0.6055(2) 0.0190(5) Uani 1 1 d . . . C35 C 0.4897(2) 0.60004(14) 0.5420(2) 0.0257(6) Uani 1 1 d . . . H35A H 0.5111 0.5710 0.4885 0.031 Uiso 1 1 calc R . . C36 C 0.3816(2) 0.61373(16) 0.5569(3) 0.0353(7) Uani 1 1 d . . . H36A H 0.3290 0.5935 0.5143 0.042 Uiso 1 1 calc R . . C37 C 0.3506(2) 0.65667(16) 0.6336(3) 0.0359(7) Uani 1 1 d . . . H37A H 0.2766 0.6658 0.6437 0.043 Uiso 1 1 calc R . . C38 C 0.4271(2) 0.68666(14) 0.6964(3) 0.0343(7) Uani 1 1 d . . . H38A H 0.4057 0.7166 0.7486 0.041 Uiso 1 1 calc R . . C39 C 0.5343(2) 0.67252(12) 0.6821(2) 0.0248(5) Uani 1 1 d . . . H39A H 0.5867 0.6927 0.7249 0.030 Uiso 1 1 calc R . . N1 N 0.66247(15) 0.49147(9) 0.65157(16) 0.0148(4) Uani 1 1 d . . . N2 N 0.75521(15) 0.42459(9) 0.55683(16) 0.0147(4) Uani 1 1 d . . . O O 0.77488(11) 0.65349(8) 0.68200(15) 0.0197(4) Uani 1 1 d . . . P1 P 0.89483(5) 0.49884(3) 0.43268(5) 0.01563(13) Uani 1 1 d . . . P2 P 0.70998(5) 0.61783(3) 0.59055(5) 0.01614(13) Uani 1 1 d . . . S1 S 0.61233(5) 0.36493(3) 0.68683(5) 0.02200(14) Uani 1 1 d . . . S2 S 0.84576(6) 0.49031(3) 0.29165(6) 0.02954(16) 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 0.0151(10) 0.0147(11) 0.0164(11) 0.0023(9) -0.0013(9) 0.0014(8) C2 0.0140(10) 0.0133(10) 0.0171(12) 0.0014(9) -0.0010(9) -0.0002(8) C3 0.0147(10) 0.0152(10) 0.0152(11) 0.0018(10) 0.0006(9) -0.0030(8) C4 0.0234(11) 0.0127(10) 0.0191(12) 0.0014(9) 0.0076(10) 0.0021(9) C5 0.0203(11) 0.0126(11) 0.0376(16) 0.0059(11) 0.0065(11) -0.0009(9) C6 0.0305(14) 0.0152(12) 0.0487(19) 0.0072(12) 0.0226(13) 0.0021(11) C7 0.0491(17) 0.0180(12) 0.0389(17) 0.0004(12) 0.0244(15) -0.0003(12) C8 0.0501(17) 0.0240(14) 0.0221(15) -0.0027(11) 0.0109(13) -0.0049(12) C9 0.0289(13) 0.0192(12) 0.0221(13) 0.0024(10) 0.0060(11) 0.0002(10) C10 0.0176(10) 0.0127(11) 0.0209(12) 0.0019(9) 0.0026(10) 0.0014(9) C11 0.0217(11) 0.0197(12) 0.0197(13) 0.0044(10) 0.0038(10) 0.0031(9) C12 0.0237(12) 0.0197(12) 0.0287(15) 0.0071(11) 0.0024(11) 0.0071(10) C13 0.0269(12) 0.0142(11) 0.0363(16) -0.0001(11) 0.0103(12) 0.0023(10) C14 0.0264(12) 0.0179(12) 0.0251(14) -0.0020(10) 0.0006(11) -0.0029(10) C15 0.0183(10) 0.0176(12) 0.0248(14) 0.0002(10) -0.0007(10) -0.0001(9) C16 0.0137(10) 0.0193(11) 0.0256(13) -0.0015(10) 0.0026(9) -0.0023(9) C17 0.0174(10) 0.0226(12) 0.0271(14) 0.0008(10) -0.0002(10) -0.0018(9) C18 0.0216(12) 0.0324(14) 0.0350(16) -0.0054(13) -0.0016(12) -0.0051(11) C19 0.0258(13) 0.0302(15) 0.049(2) -0.0049(14) 0.0040(13) -0.0136(12) C20 0.0358(15) 0.0309(15) 0.0384(17) 0.0014(13) 0.0107(13) -0.0146(13) C21 0.0283(13) 0.0248(14) 0.0267(14) 0.0010(11) 0.0058(11) -0.0072(11) C22 0.0140(10) 0.0205(12) 0.0243(13) -0.0001(10) 0.0020(9) -0.0002(9) C23 0.0210(11) 0.0306(14) 0.0261(14) -0.0038(11) -0.0008(11) 0.0069(10) C24 0.0298(13) 0.0407(17) 0.0294(15) -0.0003(14) -0.0074(13) 0.0103(12) C25 0.0234(13) 0.0399(17) 0.0427(18) -0.0019(14) 0.0004(13) 0.0147(12) C26 0.0263(13) 0.0289(14) 0.0435(19) -0.0077(13) 0.0072(13) 0.0077(11) C27 0.0216(12) 0.0252(13) 0.0289(14) -0.0058(11) 0.0038(11) -0.0010(10) C28 0.0195(11) 0.0121(10) 0.0215(12) 0.0023(9) 0.0046(9) 0.0009(9) C29 0.0191(10) 0.0159(11) 0.0251(13) 0.0007(10) 0.0027(10) -0.0021(9) C30 0.0257(12) 0.0161(12) 0.0296(14) 0.0039(10) 0.0062(11) -0.0013(10) C31 0.0250(11) 0.0210(13) 0.0245(14) 0.0057(10) 0.0025(11) 0.0035(10) C32 0.0291(12) 0.0193(12) 0.0211(13) -0.0001(10) 0.0002(11) 0.0021(10) C33 0.0281(12) 0.0164(11) 0.0246(13) 0.0002(10) 0.0016(11) -0.0027(10) C34 0.0197(10) 0.0137(10) 0.0236(13) 0.0027(9) 0.0060(10) 0.0015(9) C35 0.0257(12) 0.0278(13) 0.0235(14) -0.0007(11) 0.0007(11) 0.0039(11) C36 0.0231(13) 0.0428(17) 0.0399(18) 0.0053(14) -0.0017(12) -0.0003(12) C37 0.0257(13) 0.0391(17) 0.0429(19) 0.0096(14) 0.0105(13) 0.0156(12) C38 0.0391(15) 0.0262(14) 0.0377(17) 0.0012(13) 0.0128(14) 0.0090(12) C39 0.0312(12) 0.0168(12) 0.0263(13) -0.0010(11) 0.0074(12) -0.0013(10) N1 0.0150(8) 0.0128(9) 0.0167(10) 0.0009(8) 0.0023(8) 0.0001(7) N2 0.0153(8) 0.0111(8) 0.0177(10) 0.0007(7) 0.0011(7) 0.0000(7) O 0.0112(7) 0.0205(8) 0.0273(9) 0.0163(8) 0.0068(7) 0.0006(6) P1 0.0160(3) 0.0166(3) 0.0143(3) 0.0005(2) 0.0014(2) -0.0014(2) P2 0.0189(3) 0.0118(3) 0.0178(3) 0.0000(2) 0.0028(2) -0.0022(2) S1 0.0240(3) 0.0146(3) 0.0274(3) 0.0063(3) 0.0063(3) -0.0006(2) S2 0.0318(3) 0.0302(4) 0.0266(3) 0.0056(3) 0.0007(3) -0.0012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.369(3) . ? C1 N1 1.376(3) . ? C1 S1 1.665(2) . ? C2 C3 1.375(3) . ? C2 N2 1.407(3) . ? C2 P1 1.830(2) . ? C3 N1 1.402(3) . ? C3 P2 1.835(2) . ? C4 C9 1.380(4) . ? C4 C5 1.388(3) . ? C4 N1 1.453(3) . ? C5 C6 1.388(4) . ? C5 H5A 0.9500 . ? C6 C7 1.374(5) . ? C6 H6A 0.9500 . ? C7 C8 1.378(4) . ? C7 H7A 0.9500 . ? C8 C9 1.396(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.389(3) . ? C10 C15 1.390(4) . ? C10 N2 1.447(3) . ? C11 C12 1.392(3) . ? C11 H11A 0.9500 . ? C12 C13 1.380(4) . ? C12 H12A 0.9500 . ? C13 C14 1.394(4) . ? C13 H13A 0.9500 . ? C14 C15 1.390(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C21 1.391(4) . ? C16 C17 1.396(4) . ? C16 P1 1.808(2) . ? C17 C18 1.398(4) . ? C17 H17A 0.9500 . ? C18 C19 1.382(4) . ? C18 H18A 0.9500 . ? C19 C20 1.382(5) . ? C19 H19A 0.9500 . ? C20 C21 1.390(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.386(4) . ? C22 C27 1.395(4) . ? C22 P1 1.815(2) . ? C23 C24 1.383(4) . ? C23 H23A 0.9500 . ? C24 C25 1.391(5) . ? C24 H24A 0.9500 . ? C25 C26 1.382(5) . ? C25 H25A 0.9500 . ? C26 C27 1.388(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 C33 1.399(4) . ? C28 C29 1.404(3) . ? C28 P2 1.796(3) . ? C29 C30 1.388(4) . ? C29 H29A 0.9500 . ? C30 C31 1.387(4) . ? C30 H30A 0.9500 . ? C31 C32 1.390(4) . ? C31 H31A 0.9500 . ? C32 C33 1.379(4) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 C39 1.389(3) . ? C34 C35 1.390(4) . ? C34 P2 1.817(2) . ? C35 C36 1.389(4) . ? C35 H35A 0.9500 . ? C36 C37 1.380(5) . ? C36 H36A 0.9500 . ? C37 C38 1.393(5) . ? C37 H37A 0.9500 . ? C38 C39 1.379(4) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? O P2 1.604(2) . ? P1 S2 1.9169(10) . ? 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 104.67(19) . . ? N2 C1 S1 128.21(18) . . ? N1 C1 S1 127.12(18) . . ? C3 C2 N2 106.78(19) . . ? C3 C2 P1 133.02(17) . . ? N2 C2 P1 120.20(16) . . ? C2 C3 N1 106.20(18) . . ? C2 C3 P2 135.22(18) . . ? N1 C3 P2 118.40(16) . . ? C9 C4 C5 122.0(2) . . ? C9 C4 N1 117.9(2) . . ? C5 C4 N1 120.1(2) . . ? C6 C5 C4 117.9(3) . . ? C6 C5 H5A 121.0 . . ? C4 C5 H5A 121.0 . . ? C7 C6 C5 121.1(3) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C4 C9 C8 118.4(2) . . ? C4 C9 H9A 120.8 . . ? C8 C9 H9A 120.8 . . ? C11 C10 C15 121.4(2) . . ? C11 C10 N2 118.3(2) . . ? C15 C10 N2 120.2(2) . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C10 C15 C14 118.4(2) . . ? C10 C15 H15A 120.8 . . ? C14 C15 H15A 120.8 . . ? C21 C16 C17 120.2(2) . . ? C21 C16 P1 117.2(2) . . ? C17 C16 P1 122.24(19) . . ? C16 C17 C18 119.5(3) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C16 119.5(3) . . ? C20 C21 H21A 120.3 . . ? C16 C21 H21A 120.3 . . ? C23 C22 C27 119.6(2) . . ? C23 C22 P1 121.0(2) . . ? C27 C22 P1 119.3(2) . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 120.1(3) . . ? C23 C24 H24A 119.9 . . ? C25 C24 H24A 119.9 . . ? C26 C25 C24 119.8(3) . . ? C26 C25 H25A 120.1 . . ? C24 C25 H25A 120.1 . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C26 C27 C22 119.9(3) . . ? C26 C27 H27A 120.1 . . ? C22 C27 H27A 120.1 . . ? C33 C28 C29 119.2(2) . . ? C33 C28 P2 123.79(18) . . ? C29 C28 P2 116.2(2) . . ? C30 C29 C28 119.8(2) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C31 C30 C29 120.4(2) . . ? C31 C30 H30A 119.8 . . ? C29 C30 H30A 119.8 . . ? C30 C31 C32 119.8(3) . . ? C30 C31 H31A 120.1 . . ? C32 C31 H31A 120.1 . . ? C33 C32 C31 120.3(3) . . ? C33 C32 H32A 119.8 . . ? C31 C32 H32A 119.8 . . ? C32 C33 C28 120.4(2) . . ? C32 C33 H33A 119.8 . . ? C28 C33 H33A 119.8 . . ? C39 C34 C35 119.8(2) . . ? C39 C34 P2 116.04(19) . . ? C35 C34 P2 124.1(2) . . ? C36 C35 C34 119.8(3) . . ? C36 C35 H35A 120.1 . . ? C34 C35 H35A 120.1 . . ? C37 C36 C35 120.0(3) . . ? C37 C36 H36A 120.0 . . ? C35 C36 H36A 120.0 . . ? C36 C37 C38 120.4(3) . . ? C36 C37 H37A 119.8 . . ? C38 C37 H37A 119.8 . . ? C39 C38 C37 119.5(3) . . ? C39 C38 H38A 120.3 . . ? C37 C38 H38A 120.3 . . ? C38 C39 C34 120.5(3) . . ? C38 C39 H39A 119.7 . . ? C34 C39 H39A 119.7 . . ? C1 N1 C3 111.33(19) . . ? C1 N1 C4 121.77(19) . . ? C3 N1 C4 125.18(19) . . ? C1 N2 C2 110.96(19) . . ? C1 N2 C10 121.36(19) . . ? C2 N2 C10 127.7(2) . . ? C16 P1 C22 102.41(11) . . ? C16 P1 C2 107.22(11) . . ? C22 P1 C2 104.55(11) . . ? C16 P1 S2 115.46(9) . . ? C22 P1 S2 112.89(9) . . ? C2 P1 S2 113.19(8) . . ? O P2 C28 113.22(10) . . ? O P2 C34 111.22(10) . . ? C28 P2 C34 103.95(11) . . ? O P2 C3 114.32(10) . . ? C28 P2 C3 108.94(11) . . ? C34 P2 C3 104.34(10) . . ? 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 N2 C2 C3 N1 2.1(2) . . . . ? P1 C2 C3 N1 -177.05(19) . . . . ? N2 C2 C3 P2 -172.82(19) . . . . ? P1 C2 C3 P2 8.0(4) . . . . ? C9 C4 C5 C6 2.0(4) . . . . ? N1 C4 C5 C6 -177.9(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 -2.4(4) . . . . ? C6 C7 C8 C9 3.0(4) . . . . ? C5 C4 C9 C8 -1.4(4) . . . . ? N1 C4 C9 C8 178.6(2) . . . . ? C7 C8 C9 C4 -1.1(4) . . . . ? C15 C10 C11 C12 2.7(3) . . . . ? N2 C10 C11 C12 -178.0(2) . . . . ? C10 C11 C12 C13 -1.0(4) . . . . ? C11 C12 C13 C14 -1.1(4) . . . . ? C12 C13 C14 C15 1.6(4) . . . . ? C11 C10 C15 C14 -2.3(3) . . . . ? N2 C10 C15 C14 178.5(2) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C21 C16 C17 C18 1.3(4) . . . . ? P1 C16 C17 C18 174.34(19) . . . . ? C16 C17 C18 C19 -1.5(4) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C19 C20 C21 C16 -0.9(5) . . . . ? C17 C16 C21 C20 -0.1(4) . . . . ? P1 C16 C21 C20 -173.5(2) . . . . ? C27 C22 C23 C24 -2.4(4) . . . . ? P1 C22 C23 C24 -179.6(2) . . . . ? C22 C23 C24 C25 1.8(4) . . . . ? C23 C24 C25 C26 0.0(5) . . . . ? C24 C25 C26 C27 -1.1(5) . . . . ? C25 C26 C27 C22 0.5(4) . . . . ? C23 C22 C27 C26 1.3(4) . . . . ? P1 C22 C27 C26 178.6(2) . . . . ? C33 C28 C29 C30 -0.6(4) . . . . ? P2 C28 C29 C30 -170.34(19) . . . . ? C28 C29 C30 C31 1.1(4) . . . . ? C29 C30 C31 C32 -0.9(4) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? C31 C32 C33 C28 0.4(4) . . . . ? C29 C28 C33 C32 -0.1(4) . . . . ? P2 C28 C33 C32 168.8(2) . . . . ? C39 C34 C35 C36 -1.3(4) . . . . ? P2 C34 C35 C36 -177.3(2) . . . . ? C34 C35 C36 C37 0.9(4) . . . . ? C35 C36 C37 C38 0.2(5) . . . . ? C36 C37 C38 C39 -0.8(5) . . . . ? C37 C38 C39 C34 0.3(4) . . . . ? C35 C34 C39 C38 0.7(4) . . . . ? P2 C34 C39 C38 177.0(2) . . . . ? N2 C1 N1 C3 2.0(2) . . . . ? S1 C1 N1 C3 -177.27(18) . . . . ? N2 C1 N1 C4 -163.8(2) . . . . ? S1 C1 N1 C4 17.0(3) . . . . ? C2 C3 N1 C1 -2.6(3) . . . . ? P2 C3 N1 C1 173.34(16) . . . . ? C2 C3 N1 C4 162.5(2) . . . . ? P2 C3 N1 C4 -21.5(3) . . . . ? C9 C4 N1 C1 105.0(3) . . . . ? C5 C4 N1 C1 -75.0(3) . . . . ? C9 C4 N1 C3 -58.7(3) . . . . ? C5 C4 N1 C3 121.3(3) . . . . ? N1 C1 N2 C2 -0.6(2) . . . . ? S1 C1 N2 C2 178.66(18) . . . . ? N1 C1 N2 C10 178.6(2) . . . . ? S1 C1 N2 C10 -2.2(3) . . . . ? C3 C2 N2 C1 -1.0(3) . . . . ? P1 C2 N2 C1 178.30(16) . . . . ? C3 C2 N2 C10 179.9(2) . . . . ? P1 C2 N2 C10 -0.8(3) . . . . ? C11 C10 N2 C1 -72.9(3) . . . . ? C15 C10 N2 C1 106.4(3) . . . . ? C11 C10 N2 C2 106.1(3) . . . . ? C15 C10 N2 C2 -74.6(3) . . . . ? C21 C16 P1 C22 100.9(2) . . . . ? C17 C16 P1 C22 -72.3(2) . . . . ? C21 C16 P1 C2 -149.3(2) . . . . ? C17 C16 P1 C2 37.4(2) . . . . ? C21 C16 P1 S2 -22.2(2) . . . . ? C17 C16 P1 S2 164.62(18) . . . . ? C23 C22 P1 C16 55.3(2) . . . . ? C27 C22 P1 C16 -121.9(2) . . . . ? C23 C22 P1 C2 -56.4(2) . . . . ? C27 C22 P1 C2 126.4(2) . . . . ? C23 C22 P1 S2 -179.89(18) . . . . ? C27 C22 P1 S2 2.9(2) . . . . ? C3 C2 P1 C16 27.6(3) . . . . ? N2 C2 P1 C16 -151.49(18) . . . . ? C3 C2 P1 C22 135.9(2) . . . . ? N2 C2 P1 C22 -43.3(2) . . . . ? C3 C2 P1 S2 -100.9(2) . . . . ? N2 C2 P1 S2 80.01(19) . . . . ? C33 C28 P2 O -175.61(19) . . . . ? C29 C28 P2 O -6.4(2) . . . . ? C33 C28 P2 C34 -54.8(2) . . . . ? C29 C28 P2 C34 114.42(19) . . . . ? C33 C28 P2 C3 56.0(2) . . . . ? C29 C28 P2 C3 -134.79(18) . . . . ? C39 C34 P2 O 8.4(2) . . . . ? C35 C34 P2 O -175.5(2) . . . . ? C39 C34 P2 C28 -113.7(2) . . . . ? C35 C34 P2 C28 62.4(2) . . . . ? C39 C34 P2 C3 132.1(2) . . . . ? C35 C34 P2 C3 -51.8(2) . . . . ? C2 C3 P2 O -100.8(3) . . . . ? N1 C3 P2 O 84.70(19) . . . . ? C2 C3 P2 C28 27.0(3) . . . . ? N1 C3 P2 C28 -147.53(18) . . . . ? C2 C3 P2 C34 137.5(2) . . . . ? N1 C3 P2 C34 -37.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.458 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 888240' ####################################################################### # # 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_Greg1402f #TrackingRef 'Gesamtcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H26 N2 P2 S3' _chemical_formula_sum 'C29 H26 N2 P2 S3' _chemical_formula_weight 560.64 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' 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 2/c' 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 15.6164(16) _cell_length_b 12.2568(12) _cell_length_c 14.9796(14) _cell_angle_alpha 90.00 _cell_angle_beta 112.742(3) _cell_angle_gamma 90.00 _cell_volume 2644.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8200 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 29.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7849 _exptl_absorpt_correction_T_max 0.9588 _exptl_absorpt_process_details 'SADABS (2009/2), Bruker AXS 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8-KappaApexII' _diffrn_measurement_method '\f and \w CCD rotation images, thin slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17773 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3185 _reflns_number_gt 2866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0339P)^2^+3.1751P] 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 3185 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 C1 C 1.0000 0.24125(15) 0.2500 0.0138(3) Uani 1 2 d S . . C2 C 0.95692(9) 0.41799(11) 0.25258(9) 0.0133(3) Uani 1 1 d . . . C3 C 0.85280(9) 0.26457(11) 0.27307(10) 0.0164(3) Uani 1 1 d . . . H3C H 0.8276 0.3211 0.3024 0.025 Uiso 1 1 calc R . . H3B H 0.8724 0.2017 0.3167 0.025 Uiso 1 1 calc R . . H3A H 0.8049 0.2418 0.2112 0.025 Uiso 1 1 calc R . . C4 C 0.76610(9) 0.46565(11) 0.15424(10) 0.0144(3) Uani 1 1 d . . . C5 C 0.68339(9) 0.47713(11) 0.16837(10) 0.0165(3) Uani 1 1 d . . . H5A H 0.6834 0.5125 0.2248 0.020 Uiso 1 1 calc R . . C6 C 0.60132(10) 0.43700(12) 0.10016(11) 0.0194(3) Uani 1 1 d . . . H6A H 0.5451 0.4447 0.1100 0.023 Uiso 1 1 calc R . . C7 C 0.60083(10) 0.38542(12) 0.01732(11) 0.0219(3) Uani 1 1 d . . . H7A H 0.5444 0.3574 -0.0290 0.026 Uiso 1 1 calc R . . C8 C 0.68282(10) 0.37491(12) 0.00227(11) 0.0216(3) Uani 1 1 d . . . H8A H 0.6822 0.3406 -0.0548 0.026 Uiso 1 1 calc R . . C9 C 0.76560(10) 0.41436(12) 0.07036(10) 0.0188(3) Uani 1 1 d . . . H9A H 0.8217 0.4067 0.0602 0.023 Uiso 1 1 calc R . . C10 C 0.89190(9) 0.63883(11) 0.18022(10) 0.0153(3) Uani 1 1 d . . . C11 C 0.90810(10) 0.62451(12) 0.09553(10) 0.0191(3) Uani 1 1 d . . . H11A H 0.9216 0.5540 0.0780 0.023 Uiso 1 1 calc R . . C12 C 0.90445(11) 0.71355(13) 0.03709(11) 0.0233(3) Uani 1 1 d . . . H12A H 0.9169 0.7041 -0.0197 0.028 Uiso 1 1 calc R . . C13 C 0.88273(11) 0.81646(13) 0.06092(12) 0.0255(3) Uani 1 1 d . . . H13A H 0.8773 0.8765 0.0189 0.031 Uiso 1 1 calc R . . C14 C 0.86896(11) 0.83145(12) 0.14646(12) 0.0254(3) Uani 1 1 d . . . H14A H 0.8563 0.9023 0.1639 0.031 Uiso 1 1 calc R . . C15 C 0.87362(10) 0.74327(12) 0.20646(11) 0.0192(3) Uani 1 1 d . . . H15A H 0.8645 0.7538 0.2650 0.023 Uiso 1 1 calc R . . N N 0.93291(7) 0.30836(9) 0.25651(8) 0.0143(2) Uani 1 1 d . . . P P 0.87190(2) 0.52327(3) 0.24470(2) 0.01310(9) Uani 1 1 d . . . S1 S 1.0000 0.10444(4) 0.2500 0.01675(11) Uani 1 2 d S . . S2 S 0.86093(2) 0.55497(3) 0.36742(2) 0.01890(10) 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 0.0152(8) 0.0125(8) 0.0123(8) 0.000 0.0037(7) 0.000 C2 0.0159(6) 0.0104(6) 0.0131(6) -0.0002(5) 0.0050(5) -0.0004(5) C3 0.0151(6) 0.0155(6) 0.0202(7) 0.0008(5) 0.0085(5) -0.0019(5) C4 0.0148(6) 0.0120(6) 0.0149(6) 0.0011(5) 0.0042(5) 0.0007(5) C5 0.0184(6) 0.0133(6) 0.0188(7) 0.0024(5) 0.0083(5) 0.0019(5) C6 0.0162(6) 0.0193(7) 0.0236(7) 0.0051(6) 0.0085(6) 0.0030(5) C7 0.0186(7) 0.0209(7) 0.0213(7) 0.0006(6) 0.0024(6) -0.0019(5) C8 0.0239(7) 0.0214(7) 0.0169(7) -0.0022(6) 0.0051(6) 0.0008(6) C9 0.0174(6) 0.0201(7) 0.0194(7) -0.0007(6) 0.0075(5) 0.0016(5) C10 0.0134(6) 0.0139(6) 0.0165(6) 0.0010(5) 0.0036(5) -0.0003(5) C11 0.0223(7) 0.0161(7) 0.0176(7) -0.0005(5) 0.0064(5) -0.0001(5) C12 0.0282(8) 0.0227(7) 0.0183(7) 0.0028(6) 0.0082(6) -0.0035(6) C13 0.0253(7) 0.0180(7) 0.0317(8) 0.0086(6) 0.0094(6) -0.0011(6) C14 0.0278(8) 0.0137(7) 0.0369(9) 0.0006(6) 0.0148(7) 0.0008(6) C15 0.0199(7) 0.0157(7) 0.0240(7) -0.0013(6) 0.0106(6) -0.0003(5) N 0.0142(5) 0.0119(5) 0.0169(5) 0.0003(4) 0.0061(4) -0.0007(4) P 0.01427(17) 0.01202(17) 0.01328(16) -0.00063(12) 0.00562(13) 0.00086(12) S1 0.0196(2) 0.0107(2) 0.0197(2) 0.000 0.00731(19) 0.000 S2 0.02212(18) 0.02124(18) 0.01485(17) -0.00175(13) 0.00881(14) 0.00149(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N 1.3648(15) . ? C1 N 1.3649(15) 2_755 ? C1 S1 1.6768(19) . ? C2 C2 1.377(3) 2_755 ? C2 N 1.4025(16) . ? C2 P 1.8223(13) . ? C3 N 1.4679(16) . ? C3 H3C 0.9800 . ? C3 H3B 0.9800 . ? C3 H3A 0.9800 . ? C4 C5 1.3944(18) . ? C4 C9 1.4022(19) . ? C4 P 1.8259(14) . ? C5 C6 1.384(2) . ? C5 H5A 0.9500 . ? C6 C7 1.390(2) . ? C6 H6A 0.9500 . ? C7 C8 1.389(2) . ? C7 H7A 0.9500 . ? C8 C9 1.388(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.3973(19) . ? C10 C15 1.4005(19) . ? C10 P 1.8083(14) . ? C11 C12 1.386(2) . ? C11 H11A 0.9500 . ? C12 C13 1.388(2) . ? C12 H12A 0.9500 . ? C13 C14 1.391(2) . ? C13 H13A 0.9500 . ? C14 C15 1.390(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? P S2 1.9501(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N C1 N 105.88(16) . 2_755 ? N C1 S1 127.06(8) . . ? N C1 S1 127.06(8) 2_755 . ? C2 C2 N 106.57(7) 2_755 . ? C2 C2 P 134.39(5) 2_755 . ? N C2 P 118.77(9) . . ? N C3 H3C 109.5 . . ? N C3 H3B 109.5 . . ? H3C C3 H3B 109.5 . . ? N C3 H3A 109.5 . . ? H3C C3 H3A 109.5 . . ? H3B C3 H3A 109.5 . . ? C5 C4 C9 119.77(12) . . ? C5 C4 P 118.28(10) . . ? C9 C4 P 121.90(10) . . ? C6 C5 C4 119.99(13) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C7 120.30(13) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C8 C7 C6 119.97(13) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C9 C8 C7 120.24(14) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C4 119.72(13) . . ? C8 C9 H9A 120.1 . . ? C4 C9 H9A 120.1 . . ? C11 C10 C15 119.85(13) . . ? C11 C10 P 121.06(11) . . ? C15 C10 P 118.04(10) . . ? C12 C11 C10 119.79(13) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.49(14) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C12 C13 C14 119.80(14) . . ? C12 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? C15 C14 C13 120.33(14) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C10 119.66(14) . . ? C14 C15 H15A 120.2 . . ? C10 C15 H15A 120.2 . . ? C1 N C2 110.45(11) . . ? C1 N C3 121.31(11) . . ? C2 N C3 128.07(11) . . ? C10 P C2 108.49(6) . . ? C10 P C4 101.54(6) . . ? C2 P C4 101.64(6) . . ? C10 P S2 116.34(5) . . ? C2 P S2 114.04(5) . . ? C4 P S2 113.12(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 C9 C4 C5 C6 0.6(2) . . . . ? P C4 C5 C6 178.35(11) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C9 0.9(2) . . . . ? C7 C8 C9 C4 -0.4(2) . . . . ? C5 C4 C9 C8 -0.3(2) . . . . ? P C4 C9 C8 -177.97(11) . . . . ? C15 C10 C11 C12 -1.1(2) . . . . ? P C10 C11 C12 166.91(11) . . . . ? C10 C11 C12 C13 -1.5(2) . . . . ? C11 C12 C13 C14 3.1(2) . . . . ? C12 C13 C14 C15 -2.3(2) . . . . ? C13 C14 C15 C10 -0.3(2) . . . . ? C11 C10 C15 C14 1.9(2) . . . . ? P C10 C15 C14 -166.41(11) . . . . ? N C1 N C2 0.93(6) 2_755 . . . ? S1 C1 N C2 -179.07(6) . . . . ? N C1 N C3 -174.66(13) 2_755 . . . ? S1 C1 N C3 5.34(13) . . . . ? C2 C2 N C1 -2.44(17) 2_755 . . . ? P C2 N C1 172.44(7) . . . . ? C2 C2 N C3 172.78(14) 2_755 . . . ? P C2 N C3 -12.34(18) . . . . ? C11 C10 P C2 44.75(13) . . . . ? C15 C10 P C2 -147.04(11) . . . . ? C11 C10 P C4 -61.84(12) . . . . ? C15 C10 P C4 106.37(11) . . . . ? C11 C10 P S2 174.91(10) . . . . ? C15 C10 P S2 -16.88(12) . . . . ? C2 C2 P C10 22.5(2) 2_755 . . . ? N C2 P C10 -150.63(10) . . . . ? C2 C2 P C4 129.01(19) 2_755 . . . ? N C2 P C4 -44.11(11) . . . . ? C2 C2 P S2 -108.92(19) 2_755 . . . ? N C2 P S2 77.96(11) . . . . ? C5 C4 P C10 -108.14(11) . . . . ? C9 C4 P C10 69.53(13) . . . . ? C5 C4 P C2 139.98(11) . . . . ? C9 C4 P C2 -42.35(13) . . . . ? C5 C4 P S2 17.28(12) . . . . ? C9 C4 P S2 -165.05(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.446 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.055 #END------------------------------------------------------------------------ #--------------------------------------------------------------------------- # start Validation Reply Form # end Validation Reply Form #--------------------------------------------------------------------------- _database_code_depnum_ccdc_archive 'CCDC 888241' ####################################################################### # # 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_2501f #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H37 Cl3 N2 O3 P2 S Ti, 3(C H2 Cl2)' _chemical_formula_sum 'C37 H43 Cl9 N2 O3 P2 S Ti' _chemical_formula_weight 1024.68 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' Cl Cl 0.1484 0.1585 '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' Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1582(2) _cell_length_b 26.3418(5) _cell_length_c 17.2063(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.5660(10) _cell_angle_gamma 90.00 _cell_volume 4523.44(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7966 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.55 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.876 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9253 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58084 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.00 _reflns_number_total 10910 _reflns_number_gt 8165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0479P)^2^+1.9068P] 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 10910 _refine_ls_number_parameters 499 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Ti Ti -0.00287(4) -0.335535(15) 0.50377(3) 0.01417(10) Uani 1 1 d . . . Cl1 Cl -0.12189(6) -0.39339(2) 0.54357(4) 0.02006(13) Uani 1 1 d . . . Cl2 Cl -0.07464(6) -0.26631(2) 0.55801(4) 0.01930(13) Uani 1 1 d . . . Cl3 Cl 0.05173(6) -0.40209(2) 0.43041(4) 0.02090(13) Uani 1 1 d . . . S S -0.00447(6) -0.38733(2) 0.08212(4) 0.02257(14) Uani 1 1 d . . . P1 P 0.11675(6) -0.27197(2) 0.37607(4) 0.01461(13) Uani 1 1 d . . . P2 P -0.21996(6) -0.31143(2) 0.29601(4) 0.01435(13) Uani 1 1 d . . . O1 O 0.07048(16) -0.28516(6) 0.44343(10) 0.0164(3) Uani 1 1 d . . . O2 O -0.17135(16) -0.32643(6) 0.38932(10) 0.0162(3) Uani 1 1 d . . . O3 O 0.15385(16) -0.34214(6) 0.59336(10) 0.0202(4) Uani 1 1 d . . . N1 N 0.06700(19) -0.32411(7) 0.21991(12) 0.0155(4) Uani 1 1 d . . . N2 N -0.12846(18) -0.35968(7) 0.18112(12) 0.0149(4) Uani 1 1 d . . . C1 C 0.0198(2) -0.30722(9) 0.27740(14) 0.0152(5) Uani 1 1 d . . . C2 C -0.0228(2) -0.35676(9) 0.16127(14) 0.0165(5) Uani 1 1 d . . . C3 C -0.1042(2) -0.32877(8) 0.25230(14) 0.0145(5) Uani 1 1 d . . . C4 C 0.1882(2) -0.30936(9) 0.21306(16) 0.0209(5) Uani 1 1 d . . . H4A H 0.2552 -0.3364 0.2368 0.031 Uiso 1 1 calc R . . H4B H 0.2242 -0.2780 0.2459 0.031 Uiso 1 1 calc R . . H4C H 0.1665 -0.3038 0.1519 0.031 Uiso 1 1 calc R . . C5 C -0.2340(2) -0.39849(9) 0.13969(15) 0.0178(5) Uani 1 1 d . . . H5A H -0.2757 -0.4058 0.1786 0.021 Uiso 1 1 calc R . . H5B H -0.1918 -0.4302 0.1332 0.021 Uiso 1 1 calc R . . C6 C -0.3425(2) -0.38300(9) 0.05150(15) 0.0216(5) Uani 1 1 d . . . H6A H -0.3028 -0.3782 0.0108 0.026 Uiso 1 1 calc R . . H6B H -0.3820 -0.3503 0.0567 0.026 Uiso 1 1 calc R . . C7 C -0.4520(3) -0.42317(11) 0.01547(18) 0.0298(6) Uani 1 1 d . . . H7A H -0.4136 -0.4549 0.0053 0.036 Uiso 1 1 calc R . . H7B H -0.4846 -0.4305 0.0592 0.036 Uiso 1 1 calc R . . C8 C -0.5698(3) -0.40695(13) -0.0690(2) 0.0435(8) Uani 1 1 d . . . H8A H -0.5376 -0.3981 -0.1117 0.065 Uiso 1 1 calc R . . H8B H -0.6136 -0.3774 -0.0582 0.065 Uiso 1 1 calc R . . H8C H -0.6342 -0.4349 -0.0914 0.065 Uiso 1 1 calc R . . C9 C 0.2889(2) -0.28841(9) 0.41035(15) 0.0183(5) Uani 1 1 d . . . C10 C 0.3270(2) -0.33945(10) 0.41919(16) 0.0230(5) Uani 1 1 d . . . H10A H 0.2617 -0.3653 0.4071 0.028 Uiso 1 1 calc R . . C11 C 0.4602(3) -0.35239(11) 0.44561(17) 0.0275(6) Uani 1 1 d . . . H11A H 0.4860 -0.3871 0.4516 0.033 Uiso 1 1 calc R . . C12 C 0.5559(3) -0.31454(11) 0.46336(17) 0.0288(6) Uani 1 1 d . . . H12A H 0.6469 -0.3234 0.4807 0.035 Uiso 1 1 calc R . . C13 C 0.5188(3) -0.26403(11) 0.45582(17) 0.0297(6) Uani 1 1 d . . . H13A H 0.5848 -0.2383 0.4691 0.036 Uiso 1 1 calc R . . C14 C 0.3863(2) -0.25061(10) 0.42908(16) 0.0233(5) Uani 1 1 d . . . H14A H 0.3613 -0.2158 0.4234 0.028 Uiso 1 1 calc R . . C15 C 0.0957(2) -0.20553(8) 0.35365(15) 0.0159(5) Uani 1 1 d . . . C16 C 0.0687(2) -0.17471(9) 0.40966(15) 0.0189(5) Uani 1 1 d . . . H16A H 0.0603 -0.1890 0.4577 0.023 Uiso 1 1 calc R . . C17 C 0.0541(3) -0.12291(9) 0.39448(16) 0.0236(5) Uani 1 1 d . . . H17A H 0.0346 -0.1017 0.4321 0.028 Uiso 1 1 calc R . . C18 C 0.0676(2) -0.10156(9) 0.32535(16) 0.0227(5) Uani 1 1 d . . . H18A H 0.0595 -0.0659 0.3165 0.027 Uiso 1 1 calc R . . C19 C 0.0929(2) -0.13240(9) 0.26896(15) 0.0205(5) Uani 1 1 d . . . H19A H 0.1008 -0.1179 0.2209 0.025 Uiso 1 1 calc R . . C20 C 0.1066(2) -0.18406(9) 0.28253(15) 0.0199(5) Uani 1 1 d . . . H20A H 0.1235 -0.2051 0.2437 0.024 Uiso 1 1 calc R . . C21 C -0.3805(2) -0.34027(9) 0.23695(15) 0.0184(5) Uani 1 1 d . . . C22 C -0.4785(2) -0.31941(10) 0.15996(16) 0.0229(5) Uani 1 1 d . . . H22A H -0.4607 -0.2894 0.1363 0.027 Uiso 1 1 calc R . . C23 C -0.6023(3) -0.34322(11) 0.11870(18) 0.0306(6) Uani 1 1 d . . . H23A H -0.6692 -0.3297 0.0659 0.037 Uiso 1 1 calc R . . C24 C -0.6289(3) -0.38637(11) 0.15380(19) 0.0322(7) Uani 1 1 d . . . H24A H -0.7132 -0.4028 0.1245 0.039 Uiso 1 1 calc R . . C25 C -0.5334(3) -0.40579(11) 0.23132(19) 0.0311(6) Uani 1 1 d . . . H25A H -0.5532 -0.4350 0.2558 0.037 Uiso 1 1 calc R . . C26 C -0.4088(2) -0.38286(9) 0.27363(17) 0.0225(5) Uani 1 1 d . . . H26A H -0.3433 -0.3961 0.3272 0.027 Uiso 1 1 calc R . . C27 C -0.2390(2) -0.24428(9) 0.28038(14) 0.0156(5) Uani 1 1 d . . . C28 C -0.2667(2) -0.21624(9) 0.33904(15) 0.0200(5) Uani 1 1 d . . . H28A H -0.2703 -0.2325 0.3873 0.024 Uiso 1 1 calc R . . C29 C -0.2890(3) -0.16434(10) 0.32639(17) 0.0267(6) Uani 1 1 d . . . H29A H -0.3081 -0.1450 0.3661 0.032 Uiso 1 1 calc R . . C30 C -0.2836(3) -0.14065(10) 0.25601(17) 0.0265(6) Uani 1 1 d . . . H30A H -0.2987 -0.1051 0.2480 0.032 Uiso 1 1 calc R . . C31 C -0.2562(2) -0.16845(10) 0.19720(16) 0.0236(5) Uani 1 1 d . . . H31A H -0.2527 -0.1520 0.1491 0.028 Uiso 1 1 calc R . . C32 C -0.2340(2) -0.22021(9) 0.20905(15) 0.0205(5) Uani 1 1 d . . . H32A H -0.2155 -0.2394 0.1690 0.025 Uiso 1 1 calc R . . C33 C 0.2941(2) -0.35052(10) 0.63163(18) 0.0277(6) Uani 1 1 d . . . H33A H 0.3170 -0.3706 0.5914 0.033 Uiso 1 1 calc R . . H33B H 0.3219 -0.3702 0.6859 0.033 Uiso 1 1 calc R . . C34 C 0.3683(3) -0.30107(11) 0.6514(2) 0.0354(7) Uani 1 1 d . . . H34A H 0.3331 -0.2799 0.5991 0.053 Uiso 1 1 calc R . . H34B H 0.4638 -0.3075 0.6703 0.053 Uiso 1 1 calc R . . H34C H 0.3565 -0.2835 0.6977 0.053 Uiso 1 1 calc R . . Cl4 Cl -0.37408(8) -0.02997(3) 0.33983(5) 0.04099(19) Uani 1 1 d . . . Cl5 Cl -0.18243(9) 0.01331(3) 0.50475(5) 0.04346(19) Uani 1 1 d . . . C35 C -0.2038(3) -0.02394(12) 0.4144(2) 0.0433(8) Uani 1 1 d . . . H35A H -0.1545 -0.0082 0.3850 0.052 Uiso 1 1 calc R . . H35B H -0.1654 -0.0581 0.4346 0.052 Uiso 1 1 calc R . . Cl6 Cl -0.13141(8) 0.03376(3) 0.24020(5) 0.03723(17) Uani 1 1 d . . . Cl7 Cl -0.35837(8) -0.02098(4) 0.10739(6) 0.0515(2) Uani 1 1 d . . . C36 C -0.1905(3) -0.00288(11) 0.14454(19) 0.0336(7) Uani 1 1 d . . . H36A H -0.1814 0.0170 0.0986 0.040 Uiso 1 1 calc R . . H36B H -0.1344 -0.0337 0.1557 0.040 Uiso 1 1 calc R . . Cl8 Cl -0.79729(10) -0.00995(3) 0.21597(5) 0.0470(2) Uani 1 1 d . . . Cl9 Cl -0.66681(8) -0.00795(3) 0.10230(5) 0.03795(18) Uani 1 1 d . . . C37 C -0.8210(3) -0.00645(10) 0.10755(18) 0.0295(6) Uani 1 1 d . . . H37A H -0.8771 -0.0353 0.0741 0.035 Uiso 1 1 calc R . . H37B H -0.8689 0.0253 0.0807 0.035 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 Ti 0.0120(2) 0.0194(2) 0.0109(2) 0.00059(16) 0.00493(16) -0.00104(15) Cl1 0.0204(3) 0.0236(3) 0.0183(3) 0.0015(2) 0.0106(2) -0.0034(2) Cl2 0.0211(3) 0.0230(3) 0.0153(3) -0.0022(2) 0.0095(2) 0.0003(2) Cl3 0.0222(3) 0.0206(3) 0.0239(3) -0.0009(2) 0.0139(3) 0.0010(2) S 0.0210(3) 0.0336(3) 0.0165(3) -0.0076(3) 0.0114(3) -0.0027(3) P1 0.0117(3) 0.0209(3) 0.0119(3) -0.0014(2) 0.0059(2) -0.0022(2) P2 0.0108(3) 0.0215(3) 0.0110(3) -0.0006(2) 0.0051(2) -0.0002(2) O1 0.0166(8) 0.0219(8) 0.0130(8) -0.0018(6) 0.0088(7) -0.0029(6) O2 0.0139(8) 0.0237(8) 0.0117(8) 0.0007(6) 0.0064(7) -0.0010(6) O3 0.0141(8) 0.0276(9) 0.0155(8) 0.0033(7) 0.0035(7) 0.0011(7) N1 0.0125(10) 0.0233(10) 0.0122(9) -0.0004(8) 0.0069(8) -0.0002(8) N2 0.0118(10) 0.0214(9) 0.0115(9) -0.0014(8) 0.0052(8) -0.0011(7) C1 0.0124(11) 0.0223(11) 0.0120(11) -0.0009(9) 0.0065(9) 0.0005(9) C2 0.0149(12) 0.0224(11) 0.0125(11) 0.0012(9) 0.0063(9) 0.0015(9) C3 0.0130(11) 0.0197(11) 0.0109(11) -0.0005(9) 0.0054(9) 0.0000(9) C4 0.0157(12) 0.0308(13) 0.0195(12) -0.0024(10) 0.0108(10) -0.0039(10) C5 0.0156(12) 0.0217(11) 0.0154(11) -0.0053(9) 0.0063(10) -0.0058(9) C6 0.0161(12) 0.0310(13) 0.0160(12) -0.0032(10) 0.0058(10) -0.0015(10) C7 0.0186(13) 0.0385(15) 0.0280(14) -0.0099(12) 0.0066(11) -0.0054(11) C8 0.0215(15) 0.058(2) 0.0359(17) -0.0143(15) -0.0009(13) -0.0014(14) C9 0.0123(11) 0.0304(13) 0.0132(11) -0.0008(10) 0.0066(9) -0.0008(9) C10 0.0174(13) 0.0319(13) 0.0210(13) 0.0019(11) 0.0097(11) -0.0008(10) C11 0.0221(14) 0.0354(14) 0.0260(14) 0.0061(12) 0.0115(12) 0.0071(11) C12 0.0134(13) 0.0509(17) 0.0234(14) 0.0005(12) 0.0095(11) 0.0029(12) C13 0.0163(13) 0.0453(16) 0.0274(15) -0.0074(12) 0.0097(12) -0.0081(12) C14 0.0160(13) 0.0315(13) 0.0232(13) -0.0056(11) 0.0094(11) -0.0038(10) C15 0.0127(11) 0.0206(11) 0.0140(11) 0.0002(9) 0.0057(9) -0.0029(9) C16 0.0186(12) 0.0249(12) 0.0150(11) 0.0028(9) 0.0092(10) 0.0011(9) C17 0.0267(14) 0.0262(13) 0.0220(13) -0.0014(10) 0.0144(11) 0.0026(10) C18 0.0210(13) 0.0243(12) 0.0224(13) 0.0047(10) 0.0092(11) 0.0023(10) C19 0.0183(13) 0.0296(13) 0.0122(11) 0.0035(10) 0.0055(10) -0.0028(10) C20 0.0208(13) 0.0261(12) 0.0133(11) -0.0020(10) 0.0080(10) -0.0037(10) C21 0.0115(11) 0.0295(13) 0.0153(11) -0.0046(10) 0.0070(10) -0.0013(9) C22 0.0181(13) 0.0320(13) 0.0174(12) -0.0035(10) 0.0069(10) 0.0040(10) C23 0.0131(13) 0.0485(17) 0.0235(14) -0.0127(12) 0.0021(11) 0.0039(12) C24 0.0125(13) 0.0439(16) 0.0389(17) -0.0213(14) 0.0103(12) -0.0079(11) C25 0.0265(15) 0.0331(14) 0.0424(17) -0.0140(13) 0.0231(14) -0.0106(12) C26 0.0190(13) 0.0274(13) 0.0241(13) -0.0056(10) 0.0123(11) -0.0026(10) C27 0.0113(11) 0.0211(11) 0.0138(11) 0.0002(9) 0.0050(9) 0.0005(9) C28 0.0202(13) 0.0268(12) 0.0162(12) 0.0019(10) 0.0111(10) 0.0030(10) C29 0.0315(15) 0.0284(13) 0.0245(14) -0.0002(11) 0.0163(12) 0.0071(11) C30 0.0253(14) 0.0225(12) 0.0293(14) 0.0027(11) 0.0101(12) 0.0038(10) C31 0.0212(13) 0.0302(13) 0.0191(13) 0.0061(10) 0.0089(11) -0.0010(10) C32 0.0203(13) 0.0282(13) 0.0156(12) 0.0007(10) 0.0105(10) 0.0001(10) C33 0.0168(13) 0.0319(14) 0.0280(14) 0.0005(11) 0.0045(11) 0.0055(11) C34 0.0178(14) 0.0398(16) 0.0419(18) -0.0057(13) 0.0073(13) -0.0028(12) Cl4 0.0512(5) 0.0324(4) 0.0349(4) 0.0009(3) 0.0153(4) 0.0053(3) Cl5 0.0535(5) 0.0340(4) 0.0387(4) -0.0009(3) 0.0169(4) -0.0061(3) C35 0.046(2) 0.0490(19) 0.0364(18) 0.0096(15) 0.0200(16) 0.0113(15) Cl6 0.0516(5) 0.0345(4) 0.0331(4) -0.0077(3) 0.0256(4) -0.0076(3) Cl7 0.0316(4) 0.0837(6) 0.0401(5) -0.0051(4) 0.0168(4) -0.0097(4) C36 0.0358(17) 0.0385(16) 0.0344(16) -0.0106(13) 0.0229(14) -0.0085(13) Cl8 0.0718(6) 0.0435(4) 0.0354(4) -0.0035(3) 0.0327(4) -0.0147(4) Cl9 0.0323(4) 0.0385(4) 0.0486(5) -0.0037(3) 0.0230(4) 0.0002(3) C37 0.0302(16) 0.0311(14) 0.0279(15) -0.0018(12) 0.0135(13) 0.0018(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ti O3 1.7474(16) . ? Ti O2 2.0392(16) . ? Ti O1 2.0662(16) . ? Ti Cl1 2.3170(7) . ? Ti Cl2 2.3466(7) . ? Ti Cl3 2.3930(7) . ? S C2 1.672(2) . ? P1 O1 1.5052(16) . ? P1 C15 1.785(2) . ? P1 C9 1.792(2) . ? P1 C1 1.809(2) . ? P2 O2 1.4997(16) . ? P2 C21 1.786(2) . ? P2 C27 1.788(2) . ? P2 C3 1.820(2) . ? O3 C33 1.418(3) . ? N1 C2 1.363(3) . ? N1 C1 1.386(3) . ? N1 C4 1.462(3) . ? N2 C2 1.368(3) . ? N2 C3 1.393(3) . ? N2 C5 1.479(3) . ? C1 C3 1.374(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.514(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.523(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.397(3) . ? C9 C14 1.401(3) . ? C10 C11 1.389(3) . ? C10 H10A 0.9500 . ? C11 C12 1.391(4) . ? C11 H11A 0.9500 . ? C12 C13 1.382(4) . ? C12 H12A 0.9500 . ? C13 C14 1.384(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.393(3) . ? C15 C20 1.402(3) . ? C16 C17 1.385(3) . ? C16 H16A 0.9500 . ? C17 C18 1.383(3) . ? C17 H17A 0.9500 . ? C18 C19 1.388(3) . ? C18 H18A 0.9500 . ? C19 C20 1.378(3) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? C21 C26 1.391(3) . ? C21 C22 1.399(3) . ? C22 C23 1.388(4) . ? C22 H22A 0.9500 . ? C23 C24 1.380(4) . ? C23 H23A 0.9500 . ? C24 C25 1.380(4) . ? C24 H24A 0.9500 . ? C25 C26 1.387(3) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 C28 1.392(3) . ? C27 C32 1.404(3) . ? C28 C29 1.389(3) . ? C28 H28A 0.9500 . ? C29 C30 1.388(4) . ? C29 H29A 0.9500 . ? C30 C31 1.389(4) . ? C30 H30A 0.9500 . ? C31 C32 1.384(3) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 C34 1.498(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? Cl4 C35 1.761(3) . ? Cl5 C35 1.762(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? Cl6 C36 1.762(3) . ? Cl7 C36 1.753(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? Cl8 C37 1.766(3) . ? Cl9 C37 1.763(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? 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 Ti O2 172.01(7) . . ? O3 Ti O1 92.42(7) . . ? O2 Ti O1 80.82(6) . . ? O3 Ti Cl1 98.83(6) . . ? O2 Ti Cl1 87.71(5) . . ? O1 Ti Cl1 168.29(5) . . ? O3 Ti Cl2 96.40(6) . . ? O2 Ti Cl2 87.79(5) . . ? O1 Ti Cl2 89.03(5) . . ? Cl1 Ti Cl2 92.92(2) . . ? O3 Ti Cl3 90.11(6) . . ? O2 Ti Cl3 85.36(5) . . ? O1 Ti Cl3 87.36(5) . . ? Cl1 Ti Cl3 89.36(2) . . ? Cl2 Ti Cl3 172.69(3) . . ? O1 P1 C15 109.61(10) . . ? O1 P1 C9 112.15(10) . . ? C15 P1 C9 109.02(11) . . ? O1 P1 C1 109.70(10) . . ? C15 P1 C1 109.57(11) . . ? C9 P1 C1 106.73(11) . . ? O2 P2 C21 106.71(10) . . ? O2 P2 C27 112.55(10) . . ? C21 P2 C27 108.28(11) . . ? O2 P2 C3 113.12(10) . . ? C21 P2 C3 112.00(11) . . ? C27 P2 C3 104.18(10) . . ? P1 O1 Ti 152.19(10) . . ? P2 O2 Ti 143.19(10) . . ? C33 O3 Ti 152.44(16) . . ? C2 N1 C1 110.03(18) . . ? C2 N1 C4 120.58(19) . . ? C1 N1 C4 129.27(19) . . ? C2 N2 C3 109.66(18) . . ? C2 N2 C5 120.48(19) . . ? C3 N2 C5 128.86(18) . . ? C3 C1 N1 107.08(19) . . ? C3 C1 P1 127.04(17) . . ? N1 C1 P1 125.19(17) . . ? N1 C2 N2 106.33(19) . . ? N1 C2 S 126.11(18) . . ? N2 C2 S 127.56(18) . . ? C1 C3 N2 106.87(19) . . ? C1 C3 P2 124.57(17) . . ? N2 C3 P2 127.99(16) . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 113.85(19) . . ? N2 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? N2 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 110.9(2) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 112.8(2) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 119.5(2) . . ? C10 C9 P1 119.81(18) . . ? C14 C9 P1 120.70(19) . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C13 C14 C9 119.9(2) . . ? C13 C14 H14A 120.1 . . ? C9 C14 H14A 120.1 . . ? C16 C15 C20 120.0(2) . . ? C16 C15 P1 118.04(17) . . ? C20 C15 P1 122.00(18) . . ? C17 C16 C15 119.2(2) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C18 C17 C16 120.9(2) . . ? C18 C17 H17A 119.5 . . ? C16 C17 H17A 119.5 . . ? C17 C18 C19 119.8(2) . . ? C17 C18 H18A 120.1 . . ? C19 C18 H18A 120.1 . . ? C20 C19 C18 120.1(2) . . ? C20 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? C19 C20 C15 120.0(2) . . ? C19 C20 H20A 120.0 . . ? C15 C20 H20A 120.0 . . ? C26 C21 C22 120.4(2) . . ? C26 C21 P2 117.28(18) . . ? C22 C21 P2 122.16(19) . . ? C23 C22 C21 119.0(3) . . ? C23 C22 H22A 120.5 . . ? C21 C22 H22A 120.5 . . ? C24 C23 C22 120.5(3) . . ? C24 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C25 C24 C23 120.3(2) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C24 C25 C26 120.3(3) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C25 C26 C21 119.4(3) . . ? C25 C26 H26A 120.3 . . ? C21 C26 H26A 120.3 . . ? C28 C27 C32 120.2(2) . . ? C28 C27 P2 117.77(17) . . ? C32 C27 P2 121.98(18) . . ? C29 C28 C27 119.4(2) . . ? C29 C28 H28A 120.3 . . ? C27 C28 H28A 120.3 . . ? C30 C29 C28 120.3(2) . . ? C30 C29 H29A 119.8 . . ? C28 C29 H29A 119.8 . . ? C29 C30 C31 120.5(2) . . ? C29 C30 H30A 119.7 . . ? C31 C30 H30A 119.7 . . ? C32 C31 C30 119.7(2) . . ? C32 C31 H31A 120.2 . . ? C30 C31 H31A 120.2 . . ? C31 C32 C27 119.9(2) . . ? C31 C32 H32A 120.0 . . ? C27 C32 H32A 120.0 . . ? O3 C33 C34 110.7(2) . . ? O3 C33 H33A 109.5 . . ? C34 C33 H33A 109.5 . . ? O3 C33 H33B 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? Cl4 C35 Cl5 111.67(18) . . ? Cl4 C35 H35A 109.3 . . ? Cl5 C35 H35A 109.3 . . ? Cl4 C35 H35B 109.3 . . ? Cl5 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? Cl7 C36 Cl6 112.47(16) . . ? Cl7 C36 H36A 109.1 . . ? Cl6 C36 H36A 109.1 . . ? Cl7 C36 H36B 109.1 . . ? Cl6 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? Cl9 C37 Cl8 111.38(16) . . ? Cl9 C37 H37A 109.4 . . ? Cl8 C37 H37A 109.4 . . ? Cl9 C37 H37B 109.4 . . ? Cl8 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? 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 C15 P1 O1 Ti 155.0(2) . . . . ? C9 P1 O1 Ti -83.8(2) . . . . ? C1 P1 O1 Ti 34.7(2) . . . . ? O3 Ti O1 P1 103.9(2) . . . . ? O2 Ti O1 P1 -71.8(2) . . . . ? Cl1 Ti O1 P1 -59.9(4) . . . . ? Cl2 Ti O1 P1 -159.7(2) . . . . ? Cl3 Ti O1 P1 13.9(2) . . . . ? C21 P2 O2 Ti 156.44(16) . . . . ? C27 P2 O2 Ti -84.92(18) . . . . ? C3 P2 O2 Ti 32.8(2) . . . . ? O3 Ti O2 P2 -9.5(6) . . . . ? O1 Ti O2 P2 22.97(16) . . . . ? Cl1 Ti O2 P2 -154.65(16) . . . . ? Cl2 Ti O2 P2 112.34(16) . . . . ? Cl3 Ti O2 P2 -65.11(16) . . . . ? O2 Ti O3 C33 -16.3(7) . . . . ? O1 Ti O3 C33 -48.3(3) . . . . ? Cl1 Ti O3 C33 128.4(3) . . . . ? Cl2 Ti O3 C33 -137.6(3) . . . . ? Cl3 Ti O3 C33 39.0(3) . . . . ? C2 N1 C1 C3 -1.8(3) . . . . ? C4 N1 C1 C3 174.3(2) . . . . ? C2 N1 C1 P1 169.26(17) . . . . ? C4 N1 C1 P1 -14.7(3) . . . . ? O1 P1 C1 C3 21.3(2) . . . . ? C15 P1 C1 C3 -99.1(2) . . . . ? C9 P1 C1 C3 143.0(2) . . . . ? O1 P1 C1 N1 -147.94(19) . . . . ? C15 P1 C1 N1 91.7(2) . . . . ? C9 P1 C1 N1 -26.2(2) . . . . ? C1 N1 C2 N2 1.1(3) . . . . ? C4 N1 C2 N2 -175.36(19) . . . . ? C1 N1 C2 S -178.19(17) . . . . ? C4 N1 C2 S 5.4(3) . . . . ? C3 N2 C2 N1 0.0(2) . . . . ? C5 N2 C2 N1 -169.59(19) . . . . ? C3 N2 C2 S 179.25(18) . . . . ? C5 N2 C2 S 9.7(3) . . . . ? N1 C1 C3 N2 1.7(2) . . . . ? P1 C1 C3 N2 -169.12(17) . . . . ? N1 C1 C3 P2 -170.21(16) . . . . ? P1 C1 C3 P2 19.0(3) . . . . ? C2 N2 C3 C1 -1.0(3) . . . . ? C5 N2 C3 C1 167.4(2) . . . . ? C2 N2 C3 P2 170.47(17) . . . . ? C5 N2 C3 P2 -21.1(3) . . . . ? O2 P2 C3 C1 -68.2(2) . . . . ? C21 P2 C3 C1 171.2(2) . . . . ? C27 P2 C3 C1 54.4(2) . . . . ? O2 P2 C3 N2 121.7(2) . . . . ? C21 P2 C3 N2 1.1(2) . . . . ? C27 P2 C3 N2 -115.8(2) . . . . ? C2 N2 C5 C6 -84.3(3) . . . . ? C3 N2 C5 C6 108.3(3) . . . . ? N2 C5 C6 C7 -176.3(2) . . . . ? C5 C6 C7 C8 174.4(2) . . . . ? O1 P1 C9 C10 68.0(2) . . . . ? C15 P1 C9 C10 -170.43(19) . . . . ? C1 P1 C9 C10 -52.2(2) . . . . ? O1 P1 C9 C14 -111.5(2) . . . . ? C15 P1 C9 C14 10.1(2) . . . . ? C1 P1 C9 C14 128.3(2) . . . . ? C14 C9 C10 C11 -0.6(4) . . . . ? P1 C9 C10 C11 179.90(19) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? C12 C13 C14 C9 0.7(4) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? P1 C9 C14 C13 179.72(19) . . . . ? O1 P1 C15 C16 12.6(2) . . . . ? C9 P1 C15 C16 -110.50(19) . . . . ? C1 P1 C15 C16 133.04(18) . . . . ? O1 P1 C15 C20 -167.84(18) . . . . ? C9 P1 C15 C20 69.1(2) . . . . ? C1 P1 C15 C20 -47.4(2) . . . . ? C20 C15 C16 C17 -0.6(4) . . . . ? P1 C15 C16 C17 178.97(19) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C16 C17 C18 C19 1.5(4) . . . . ? C17 C18 C19 C20 -1.0(4) . . . . ? C18 C19 C20 C15 -0.4(4) . . . . ? C16 C15 C20 C19 1.1(3) . . . . ? P1 C15 C20 C19 -178.41(18) . . . . ? O2 P2 C21 C26 -23.1(2) . . . . ? C27 P2 C21 C26 -144.45(19) . . . . ? C3 P2 C21 C26 101.2(2) . . . . ? O2 P2 C21 C22 152.51(19) . . . . ? C27 P2 C21 C22 31.1(2) . . . . ? C3 P2 C21 C22 -83.2(2) . . . . ? C26 C21 C22 C23 -2.9(4) . . . . ? P2 C21 C22 C23 -178.38(19) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C22 C23 C24 C25 1.3(4) . . . . ? C23 C24 C25 C26 -1.6(4) . . . . ? C24 C25 C26 C21 -0.4(4) . . . . ? C22 C21 C26 C25 2.6(4) . . . . ? P2 C21 C26 C25 178.31(19) . . . . ? O2 P2 C27 C28 -27.6(2) . . . . ? C21 P2 C27 C28 90.1(2) . . . . ? C3 P2 C27 C28 -150.56(19) . . . . ? O2 P2 C27 C32 155.81(18) . . . . ? C21 P2 C27 C32 -86.5(2) . . . . ? C3 P2 C27 C32 32.9(2) . . . . ? C32 C27 C28 C29 -0.1(4) . . . . ? P2 C27 C28 C29 -176.70(19) . . . . ? C27 C28 C29 C30 -0.1(4) . . . . ? C28 C29 C30 C31 0.2(4) . . . . ? C29 C30 C31 C32 -0.1(4) . . . . ? C30 C31 C32 C27 -0.1(4) . . . . ? C28 C27 C32 C31 0.2(4) . . . . ? P2 C27 C32 C31 176.68(19) . . . . ? Ti O3 C33 C34 94.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.801 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 934725'