# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_MAS _database_code_depnum_ccdc_archive 'CCDC 847125' #TrackingRef 'web_deposit_cif_file_0_LauraRoces_1329933141.complex12_CCDC847125.cif' _audit_creation_date 2011-10-02T19:17:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C30 H33 N P2 S' _chemical_formula_sum 'C30 H33 N P2 S' _chemical_formula_weight 501.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 13.6300(5) _cell_length_b 10.2681(3) _cell_length_c 22.3237(6) _cell_angle_alpha 90 _cell_angle_beta 119.548(2) _cell_angle_gamma 90 _cell_volume 2717.96(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9585 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.41 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 1.41 _exptl_crystal_size_mid 0.429 _exptl_crystal_size_min 0.339 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Linear fit to sin(theta)/lambda - 12 parameters ; _exptl_absorpt_correction_T_min 0.6756 _exptl_absorpt_correction_T_max 1.0473 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_reflns_av_R_equivalents 0.0906 _diffrn_reflns_av_unetI/netI 0.0585 _diffrn_reflns_number 13903 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.42 _diffrn_reflns_theta_full 24.42 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4468 _reflns_number_gt 4164 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material ; WinGX Publication Routines enCIFer ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0518P)^2^+1.6859P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4468 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.108 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.62 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.061 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.74810(4) 0.82133(5) 0.20999(2) 0.01799(14) Uani 1 1 d . . . P2 P 0.84515(4) 0.72584(5) 0.10452(2) 0.01770(14) Uani 1 1 d . . . N1 N 0.70492(13) 0.91181(16) 0.25452(8) 0.0235(4) Uani 1 1 d . . . S1 S 0.67981(4) 0.64935(5) 0.18373(3) 0.02435(15) Uani 1 1 d . . . C28 C 0.77138(16) 1.0307(2) 0.28940(10) 0.0256(4) Uani 1 1 d . . . H28 H 0.8182 1.0519 0.2675 0.031 Uiso 1 1 calc R . . C29 C 0.69757(19) 1.1498(2) 0.27983(12) 0.0360(5) Uani 1 1 d . . . H29A H 0.6404 1.1582 0.2311 0.054 Uiso 1 1 calc R . . H29B H 0.7447 1.2282 0.2947 0.054 Uiso 1 1 calc R . . H29C H 0.6603 1.1393 0.3075 0.054 Uiso 1 1 calc R . . C30 C 0.85273(17) 1.0073(2) 0.36570(11) 0.0302(5) Uani 1 1 d . . . H30C H 0.8099 0.9852 0.389 0.045 Uiso 1 1 calc R . . H30B H 0.897 1.0864 0.3863 0.045 Uiso 1 1 calc R . . H30A H 0.9036 0.9354 0.3709 0.045 Uiso 1 1 calc R . . C25 C 0.61740(18) 0.8747(2) 0.27265(13) 0.0358(5) Uani 1 1 d . . . H25 H 0.6201 0.9469 0.3035 0.043 Uiso 1 1 calc R . . C27 C 0.6434(2) 0.7562(3) 0.31665(15) 0.0509(7) Uani 1 1 d . . . H27A H 0.6241 0.6782 0.2877 0.076 Uiso 1 1 calc R . . H27C H 0.5991 0.7578 0.3404 0.076 Uiso 1 1 calc R . . H27B H 0.7239 0.7549 0.3507 0.076 Uiso 1 1 calc R . . C26 C 0.49992(18) 0.8836(3) 0.21212(14) 0.0437(6) Uani 1 1 d . . . H26B H 0.4899 0.9682 0.1895 0.066 Uiso 1 1 calc R . . H26C H 0.445 0.8747 0.2281 0.066 Uiso 1 1 calc R . . H26A H 0.4884 0.8138 0.1794 0.066 Uiso 1 1 calc R . . C19 C 0.93839(15) 0.78454(17) 0.07230(10) 0.0191(4) Uani 1 1 d . . . C20 C 0.92720(16) 0.75402(19) 0.00851(10) 0.0243(4) Uani 1 1 d . . . H20 H 0.8649 0.7034 -0.0234 0.029 Uiso 1 1 calc R . . C21 C 1.00655(18) 0.7971(2) -0.00891(11) 0.0295(5) Uani 1 1 d . . . H21 H 0.9989 0.7741 -0.0522 0.035 Uiso 1 1 calc R . . C22 C 1.09638(18) 0.8729(2) 0.03625(12) 0.0305(5) Uani 1 1 d . . . H22 H 1.1499 0.9027 0.0239 0.037 Uiso 1 1 calc R . . C23 C 1.10824(17) 0.9055(2) 0.09964(12) 0.0284(5) Uani 1 1 d . . . H23 H 1.1694 0.9586 0.1307 0.034 Uiso 1 1 calc R . . C24 C 1.03036(16) 0.86023(19) 0.11767(11) 0.0242(4) Uani 1 1 d . . . H24 H 1.0398 0.8811 0.1617 0.029 Uiso 1 1 calc R . . C13 C 0.74957(15) 0.61538(18) 0.03591(9) 0.0194(4) Uani 1 1 d . . . C14 C 0.79524(16) 0.50298(18) 0.02452(10) 0.0219(4) Uani 1 1 d . . . H14 H 0.8745 0.4894 0.0498 0.026 Uiso 1 1 calc R . . C15 C 0.72713(17) 0.41096(19) -0.02293(11) 0.0265(4) Uani 1 1 d . . . H15 H 0.7597 0.3355 -0.0306 0.032 Uiso 1 1 calc R . . C16 C 0.61204(17) 0.4284(2) -0.05917(11) 0.0321(5) Uani 1 1 d . . . H16 H 0.5651 0.3651 -0.0918 0.039 Uiso 1 1 calc R . . C17 C 0.56536(17) 0.5383(2) -0.04779(13) 0.0385(6) Uani 1 1 d . . . H17 H 0.486 0.5505 -0.0726 0.046 Uiso 1 1 calc R . . C18 C 0.63365(17) 0.6310(2) -0.00041(12) 0.0310(5) Uani 1 1 d . . . H18 H 0.6006 0.7061 0.0072 0.037 Uiso 1 1 calc R . . C7 C 0.90132(15) 0.81388(18) 0.26153(9) 0.0179(4) Uani 1 1 d . . . C12 C 0.97001(15) 0.91281(18) 0.25990(9) 0.0199(4) Uani 1 1 d . . . H12 H 0.937 0.9858 0.2306 0.024 Uiso 1 1 calc R . . C11 C 1.08621(15) 0.90530(19) 0.30079(10) 0.0229(4) Uani 1 1 d . . . H11 H 1.1326 0.9731 0.2996 0.027 Uiso 1 1 calc R . . C10 C 1.13433(16) 0.7988(2) 0.34326(10) 0.0249(4) Uani 1 1 d . . . H10 H 1.214 0.7929 0.3709 0.03 Uiso 1 1 calc R . . C9 C 1.06696(16) 0.7009(2) 0.34567(10) 0.0240(4) Uani 1 1 d . . . H9 H 1.1003 0.6285 0.3754 0.029 Uiso 1 1 calc R . . C8 C 0.95061(16) 0.70828(18) 0.30479(9) 0.0206(4) Uani 1 1 d . . . H8 H 0.9045 0.6406 0.3065 0.025 Uiso 1 1 calc R . . C1 C 0.71877(14) 0.91389(18) 0.13266(9) 0.0189(4) Uani 1 1 d . . . C2 C 0.75545(14) 0.87220(17) 0.08690(9) 0.0180(4) Uani 1 1 d . . . C3 C 0.72182(15) 0.94274(19) 0.02626(10) 0.0221(4) Uani 1 1 d . . . H3 H 0.7455 0.9147 -0.0051 0.027 Uiso 1 1 calc R . . C4 C 0.65462(15) 1.05275(19) 0.01092(10) 0.0253(4) Uani 1 1 d . . . H4 H 0.6336 1.1001 -0.0302 0.03 Uiso 1 1 calc R . . C5 C 0.61840(15) 1.09307(19) 0.05581(11) 0.0262(4) Uani 1 1 d . . . H5 H 0.5721 1.1682 0.0456 0.031 Uiso 1 1 calc R . . C6 C 0.64971(15) 1.02376(19) 0.11580(10) 0.0232(4) Uani 1 1 d . . . H6 H 0.6237 1.0515 0.1461 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0165(2) 0.0204(3) 0.0173(3) -0.00248(19) 0.0085(2) -0.00147(17) P2 0.0179(2) 0.0189(3) 0.0162(2) -0.00085(19) 0.0084(2) 0.00007(17) N1 0.0215(8) 0.0280(9) 0.0245(8) -0.0058(7) 0.0141(7) -0.0016(7) S1 0.0237(3) 0.0233(3) 0.0265(3) -0.0056(2) 0.0128(2) -0.00658(18) C28 0.0244(9) 0.0271(11) 0.0247(10) -0.0065(9) 0.0117(9) 0.0004(8) C29 0.0326(11) 0.0341(12) 0.0355(12) -0.0116(10) 0.0123(10) 0.0051(9) C30 0.0282(10) 0.0340(11) 0.0258(11) -0.0076(9) 0.0114(9) -0.0024(9) C25 0.0353(12) 0.0428(13) 0.0431(13) -0.0027(11) 0.0299(11) -0.0010(10) C27 0.0578(16) 0.0580(16) 0.0489(15) 0.0003(14) 0.0354(14) -0.0156(13) C26 0.0281(11) 0.0489(14) 0.0585(16) -0.0097(13) 0.0246(12) -0.0098(10) C19 0.0190(9) 0.0187(9) 0.0207(9) 0.0022(8) 0.0105(8) 0.0032(7) C20 0.0281(10) 0.0240(10) 0.0221(10) 0.0018(8) 0.0134(9) 0.0012(8) C21 0.0398(11) 0.0277(11) 0.0293(11) 0.0046(9) 0.0233(10) 0.0034(9) C22 0.0338(11) 0.0235(10) 0.0463(13) 0.0076(10) 0.0290(11) 0.0041(9) C23 0.0249(10) 0.0229(10) 0.0394(12) -0.0003(9) 0.0174(9) -0.0009(8) C24 0.0243(10) 0.0241(10) 0.0263(10) -0.0025(8) 0.0141(9) 0.0007(8) C13 0.0233(9) 0.0198(9) 0.0170(9) -0.0006(8) 0.0114(8) -0.0030(7) C14 0.0223(9) 0.0237(10) 0.0195(9) 0.0022(8) 0.0101(8) 0.0007(7) C15 0.0321(11) 0.0216(10) 0.0283(11) -0.0039(9) 0.0169(9) -0.0011(8) C16 0.0303(11) 0.0314(12) 0.0313(11) -0.0117(10) 0.0127(10) -0.0086(9) C17 0.0204(10) 0.0381(13) 0.0462(14) -0.0146(11) 0.0081(10) -0.0029(9) C18 0.0231(10) 0.0293(11) 0.0365(12) -0.0093(10) 0.0115(9) 0.0004(8) C7 0.0184(9) 0.0209(9) 0.0155(9) -0.0031(8) 0.0091(8) 0.0008(7) C12 0.0224(9) 0.0213(9) 0.0165(9) -0.0011(8) 0.0099(8) 0.0003(7) C11 0.0213(9) 0.0260(10) 0.0214(10) -0.0055(8) 0.0106(8) -0.0039(8) C10 0.0188(9) 0.0314(11) 0.0189(9) -0.0052(9) 0.0051(8) 0.0031(8) C9 0.0283(10) 0.0247(10) 0.0153(9) -0.0005(8) 0.0078(8) 0.0074(8) C8 0.0284(10) 0.0191(9) 0.0169(9) -0.0012(8) 0.0132(8) -0.0003(7) C1 0.0144(8) 0.0196(9) 0.0179(9) -0.0025(8) 0.0044(7) -0.0022(7) C2 0.0143(8) 0.0180(9) 0.0169(9) -0.0008(7) 0.0040(7) -0.0028(7) C3 0.0209(9) 0.0238(10) 0.0196(9) 0.0000(8) 0.0084(8) -0.0036(7) C4 0.0205(9) 0.0247(10) 0.0224(10) 0.0044(8) 0.0043(8) -0.0018(8) C5 0.0184(9) 0.0222(10) 0.0278(10) 0.0002(9) 0.0036(8) 0.0028(7) C6 0.0174(9) 0.0254(10) 0.0224(10) -0.0039(8) 0.0065(8) 0.0006(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.6658(16) . ? P1 C7 1.8224(18) . ? P1 C1 1.8336(19) . ? P1 S1 1.9469(6) . ? P2 C13 1.8334(19) . ? P2 C19 1.8432(18) . ? P2 C2 1.8531(18) . ? N1 C25 1.486(3) . ? N1 C28 1.491(2) . ? C28 C30 1.525(3) . ? C28 C29 1.530(3) . ? C28 H28 1 . ? C29 H29A 0.98 . ? C29 H29B 0.98 . ? C29 H29C 0.98 . ? C30 H30C 0.98 . ? C30 H30B 0.98 . ? C30 H30A 0.98 . ? C25 C27 1.493(4) . ? C25 C26 1.505(3) . ? C25 H25 1 . ? C27 H27A 0.98 . ? C27 H27C 0.98 . ? C27 H27B 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C26 H26A 0.98 . ? C19 C20 1.391(3) . ? C19 C24 1.396(3) . ? C20 C21 1.390(3) . ? C20 H20 0.95 . ? C21 C22 1.380(3) . ? C21 H21 0.95 . ? C22 C23 1.384(3) . ? C22 H22 0.95 . ? C23 C24 1.388(3) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? C13 C18 1.384(3) . ? C13 C14 1.393(3) . ? C14 C15 1.381(3) . ? C14 H14 0.95 . ? C15 C16 1.377(3) . ? C15 H15 0.95 . ? C16 C17 1.379(3) . ? C16 H16 0.95 . ? C17 C18 1.386(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C7 C8 1.386(3) . ? C7 C12 1.394(3) . ? C12 C11 1.386(3) . ? C12 H12 0.95 . ? C11 C10 1.383(3) . ? C11 H11 0.95 . ? C10 C9 1.380(3) . ? C10 H10 0.95 . ? C9 C8 1.388(3) . ? C9 H9 0.95 . ? C8 H8 0.95 . ? C1 C6 1.397(3) . ? C1 C2 1.407(3) . ? C2 C3 1.398(3) . ? C3 C4 1.387(3) . ? C3 H3 0.95 . ? C4 C5 1.381(3) . ? C4 H4 0.95 . ? C5 C6 1.385(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? 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 P1 C7 106.18(8) . . ? N1 P1 C1 107.19(9) . . ? C7 P1 C1 105.43(8) . . ? N1 P1 S1 115.37(6) . . ? C7 P1 S1 112.39(6) . . ? C1 P1 S1 109.68(6) . . ? C13 P2 C19 102.65(8) . . ? C13 P2 C2 101.64(8) . . ? C19 P2 C2 99.31(8) . . ? C25 N1 C28 115.49(16) . . ? C25 N1 P1 125.94(14) . . ? C28 N1 P1 117.78(12) . . ? N1 C28 C30 111.98(17) . . ? N1 C28 C29 113.16(16) . . ? C30 C28 C29 110.34(17) . . ? N1 C28 H28 107 . . ? C30 C28 H28 107 . . ? C29 C28 H28 107 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30C 109.5 . . ? C28 C30 H30B 109.5 . . ? H30C C30 H30B 109.5 . . ? C28 C30 H30A 109.5 . . ? H30C C30 H30A 109.5 . . ? H30B C30 H30A 109.5 . . ? N1 C25 C27 115.25(19) . . ? N1 C25 C26 112.4(2) . . ? C27 C25 C26 116.3(2) . . ? N1 C25 H25 103.6 . . ? C27 C25 H25 103.6 . . ? C26 C25 H25 103.6 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? H27C C27 H27B 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C26 H26A 109.5 . . ? H26B C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? C20 C19 C24 118.30(17) . . ? C20 C19 P2 125.25(14) . . ? C24 C19 P2 116.37(14) . . ? C21 C20 C19 120.48(19) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 120.50(19) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.84(18) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 119.69(19) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C19 121.17(19) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? C18 C13 C14 118.23(17) . . ? C18 C13 P2 123.58(15) . . ? C14 C13 P2 117.88(14) . . ? C15 C14 C13 121.00(17) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 120.12(18) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.59(19) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 120.36(19) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 120.68(19) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C8 C7 C12 119.17(17) . . ? C8 C7 P1 118.93(14) . . ? C12 C7 P1 121.89(14) . . ? C11 C12 C7 120.41(18) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C10 C11 C12 119.80(18) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C9 C10 C11 120.19(17) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C9 C8 120.10(18) . . ? C10 C9 H9 120 . . ? C8 C9 H9 120 . . ? C7 C8 C9 120.32(18) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C6 C1 C2 118.91(17) . . ? C6 C1 P1 118.52(14) . . ? C2 C1 P1 122.35(14) . . ? C3 C2 C1 118.75(17) . . ? C3 C2 P2 119.50(14) . . ? C1 C2 P2 121.74(14) . . ? C4 C3 C2 121.48(19) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 119.60(19) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.84(18) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 121.40(18) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? data_newd _database_code_depnum_ccdc_archive 'CCDC 847136' #TrackingRef 'web_deposit_cif_file_1_LauraRoces_1329933141.complex9_CCDC847136.cif' _audit_creation_date 2011-07-26T22:16:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H32 N P S Sn' _chemical_formula_sum 'C21 H32 N P S Sn' _chemical_formula_weight 480.2 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 10.62370(10) _cell_length_b 16.3773(2) _cell_length_c 15.8989(2) _cell_angle_alpha 90 _cell_angle_beta 125.4060(10) _cell_angle_gamma 90 _cell_volume 2254.65(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10634 _cell_measurement_theta_min 3.4078 _cell_measurement_theta_max 68.4261 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 10.562 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.5559 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.264 _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_unetI/netI 0.0253 _diffrn_reflns_number 14406 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 68.55 _diffrn_reflns_theta_full 67.5 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 4097 _reflns_number_gt 3813 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SIR-92 (Giacovazzo, 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material ; WinGX Publication Routines enCIFer ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0407P)^2^+1.3175P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4097 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.439 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Sn1 Sn 0.064997(18) 0.324191(10) 0.651677(13) 0.02173(8) Uani 1 1 d . . . P1 P 0.46408(7) 0.41188(4) 0.77903(5) 0.01775(14) Uani 1 1 d . . . S1 S 0.44547(7) 0.31143(4) 0.83778(5) 0.02632(16) Uani 1 1 d . . . N1 N 0.6207(2) 0.46796(14) 0.85926(16) 0.0212(5) Uani 1 1 d . . . C1 C 0.3000(3) 0.47983(15) 0.73271(18) 0.0179(5) Uani 1 1 d . . . C2 C 0.1487(3) 0.44947(15) 0.68348(19) 0.0186(5) Uani 1 1 d . . . C3 C 0.0298(3) 0.50690(17) 0.6453(2) 0.0239(6) Uani 1 1 d . . . H3 H -0.0732 0.488 0.612 0.029 Uiso 1 1 calc R . . C4 C 0.0567(3) 0.59035(18) 0.6542(2) 0.0271(6) Uani 1 1 d . . . H4 H -0.0269 0.6275 0.6274 0.033 Uiso 1 1 calc R . . C5 C 0.2057(3) 0.61938(17) 0.7022(2) 0.0264(6) Uani 1 1 d . . . H5 H 0.2252 0.6765 0.7089 0.032 Uiso 1 1 calc R . . C6 C 0.3264(3) 0.56415(16) 0.7404(2) 0.0234(5) Uani 1 1 d . . . H6 H 0.4286 0.5839 0.7724 0.028 Uiso 1 1 calc R . . C7 C 0.4556(3) 0.39019(15) 0.66384(19) 0.0184(5) Uani 1 1 d . . . C8 C 0.5058(3) 0.31457(16) 0.6529(2) 0.0270(6) Uani 1 1 d . . . H8 H 0.5467 0.2754 0.7067 0.032 Uiso 1 1 calc R . . C9 C 0.4963(3) 0.29641(18) 0.5649(2) 0.0321(7) Uani 1 1 d . . . H9 H 0.5329 0.2453 0.559 0.039 Uiso 1 1 calc R . . C10 C 0.4339(3) 0.35213(19) 0.4851(2) 0.0289(6) Uani 1 1 d . . . H10 H 0.4282 0.3395 0.4246 0.035 Uiso 1 1 calc R . . C11 C 0.3798(3) 0.42641(18) 0.4935(2) 0.0262(6) Uani 1 1 d . . . H11 H 0.3353 0.4645 0.4383 0.031 Uiso 1 1 calc R . . C12 C 0.3904(3) 0.44526(17) 0.58260(19) 0.0223(5) Uani 1 1 d . . . H12 H 0.3528 0.4962 0.5879 0.027 Uiso 1 1 calc R . . C13 C -0.1799(3) 0.34117(19) 0.5374(2) 0.0348(7) Uani 1 1 d . . . H13A H -0.222 0.3755 0.5661 0.052 Uiso 1 1 calc R . . H13B H -0.2317 0.288 0.5178 0.052 Uiso 1 1 calc R . . H13C H -0.1972 0.3678 0.4763 0.052 Uiso 1 1 calc R . . C14 C 0.0768(3) 0.2650(2) 0.7765(2) 0.0354(7) Uani 1 1 d . . . H14A H 0.0425 0.3029 0.8071 0.053 Uiso 1 1 calc R . . H14B H 0.1835 0.2483 0.8291 0.053 Uiso 1 1 calc R . . H14C H 0.0099 0.2168 0.7504 0.053 Uiso 1 1 calc R . . C15 C 0.1365(4) 0.24854(19) 0.5766(2) 0.0361(7) Uani 1 1 d . . . H15A H 0.1283 0.2793 0.5208 0.054 Uiso 1 1 calc R . . H15B H 0.0701 0.2002 0.5481 0.054 Uiso 1 1 calc R . . H15C H 0.2439 0.2315 0.6267 0.054 Uiso 1 1 calc R . . C16 C 0.6479(3) 0.48344(19) 0.9613(2) 0.0315(7) Uani 1 1 d . . . H16 H 0.5491 0.4707 0.9528 0.038 Uiso 1 1 calc R . . C17 C 0.6847(4) 0.5726(2) 0.9938(2) 0.0390(8) Uani 1 1 d . . . H17A H 0.6039 0.6074 0.9384 0.059 Uiso 1 1 calc R . . H17B H 0.7845 0.5868 1.0073 0.059 Uiso 1 1 calc R . . H17C H 0.6892 0.5811 1.0565 0.059 Uiso 1 1 calc R . . C18 C 0.7715(5) 0.4273(2) 1.0464(2) 0.0544(10) Uani 1 1 d . . . H18A H 0.7451 0.3703 1.024 0.082 Uiso 1 1 calc R . . H18B H 0.7765 0.4353 1.1093 0.082 Uiso 1 1 calc R . . H18C H 0.872 0.4403 1.0603 0.082 Uiso 1 1 calc R . . C19 C 0.7563(3) 0.4818(2) 0.8569(2) 0.0341(7) Uani 1 1 d . . . H19 H 0.8362 0.5075 0.9247 0.041 Uiso 1 1 calc R . . C20 C 0.8303(4) 0.4038(3) 0.8517(4) 0.0767(16) Uani 1 1 d . . . H20A H 0.849 0.3658 0.9055 0.115 Uiso 1 1 calc R . . H20B H 0.9286 0.4172 0.8624 0.115 Uiso 1 1 calc R . . H20C H 0.7609 0.3783 0.7838 0.115 Uiso 1 1 calc R . . C21 C 0.7238(5) 0.5440(3) 0.7754(3) 0.0626(13) Uani 1 1 d . . . H21A H 0.6768 0.5928 0.782 0.094 Uiso 1 1 calc R . . H21B H 0.6529 0.5202 0.7066 0.094 Uiso 1 1 calc R . . H21C H 0.8208 0.5589 0.7852 0.094 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 Sn1 0.01892(11) 0.01941(11) 0.02459(12) 0.00117(7) 0.01130(9) -0.00077(6) P1 0.0156(3) 0.0196(3) 0.0165(3) 0.0031(2) 0.0084(3) 0.0015(2) S1 0.0243(3) 0.0257(3) 0.0278(4) 0.0104(3) 0.0144(3) 0.0032(3) N1 0.0170(10) 0.0295(12) 0.0159(11) 0.0000(9) 0.0088(9) -0.0015(9) C1 0.0182(12) 0.0208(13) 0.0134(12) 0.0001(10) 0.0085(10) -0.0005(10) C2 0.0207(12) 0.0179(12) 0.0181(12) -0.0001(10) 0.0118(11) 0.0009(10) C3 0.0179(12) 0.0260(14) 0.0244(14) -0.0026(11) 0.0103(11) 0.0011(11) C4 0.0245(14) 0.0250(15) 0.0294(16) 0.0023(11) 0.0142(13) 0.0078(11) C5 0.0298(14) 0.0180(13) 0.0314(15) -0.0020(11) 0.0177(13) 0.0010(11) C6 0.0218(12) 0.0224(13) 0.0233(14) -0.0002(11) 0.0116(11) 0.0003(11) C7 0.0133(11) 0.0205(13) 0.0192(13) -0.0022(10) 0.0082(10) -0.0020(10) C8 0.0274(14) 0.0210(14) 0.0354(17) 0.0035(12) 0.0199(13) 0.0015(11) C9 0.0368(16) 0.0249(15) 0.0481(19) -0.0114(14) 0.0323(15) -0.0041(13) C10 0.0236(13) 0.0391(17) 0.0273(15) -0.0121(13) 0.0166(12) -0.0079(13) C11 0.0198(12) 0.0373(16) 0.0185(13) -0.0003(12) 0.0094(11) 0.0013(12) C12 0.0194(12) 0.0244(14) 0.0200(13) -0.0008(11) 0.0096(11) 0.0028(11) C13 0.0246(14) 0.0327(16) 0.0360(17) 0.0005(14) 0.0112(13) -0.0022(13) C14 0.0327(15) 0.0365(17) 0.0379(17) 0.0095(14) 0.0210(14) -0.0021(13) C15 0.0389(16) 0.0306(16) 0.0398(18) -0.0089(14) 0.0234(15) -0.0020(13) C16 0.0328(15) 0.0426(18) 0.0238(15) -0.0084(13) 0.0191(13) -0.0114(13) C17 0.0346(16) 0.050(2) 0.0336(17) -0.0188(15) 0.0201(14) -0.0133(15) C18 0.070(3) 0.054(2) 0.0171(16) 0.0035(15) 0.0120(17) -0.011(2) C19 0.0165(12) 0.059(2) 0.0239(15) -0.0124(14) 0.0103(12) -0.0100(13) C20 0.0209(16) 0.113(4) 0.078(3) -0.045(3) 0.0183(19) 0.006(2) C21 0.061(2) 0.101(3) 0.0272(18) -0.018(2) 0.0264(18) -0.055(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Sn1 C15 2.141(3) . ? Sn1 C14 2.146(3) . ? Sn1 C13 2.161(3) . ? Sn1 C2 2.176(3) . ? P1 N1 1.667(2) . ? P1 C7 1.816(3) . ? P1 C1 1.825(3) . ? P1 S1 1.9576(9) . ? N1 C19 1.480(3) . ? N1 C16 1.495(3) . ? C1 C6 1.400(4) . ? C1 C2 1.410(3) . ? C2 C3 1.400(4) . ? C3 C4 1.387(4) . ? C3 H3 0.95 . ? C4 C5 1.383(4) . ? C4 H4 0.95 . ? C5 C6 1.389(4) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C12 1.387(4) . ? C7 C8 1.398(4) . ? C8 C9 1.376(4) . ? C8 H8 0.95 . ? C9 C10 1.381(4) . ? C9 H9 0.95 . ? C10 C11 1.385(4) . ? C10 H10 0.95 . ? C11 C12 1.389(4) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 C17 1.523(4) . ? C16 C18 1.530(5) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 C21 1.521(5) . ? C19 C20 1.528(5) . ? C19 H19 1 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? 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 C15 Sn1 C14 113.85(13) . . ? C15 Sn1 C13 104.40(12) . . ? C14 Sn1 C13 103.46(12) . . ? C15 Sn1 C2 116.49(11) . . ? C14 Sn1 C2 114.44(11) . . ? C13 Sn1 C2 101.82(11) . . ? N1 P1 C7 108.89(11) . . ? N1 P1 C1 105.62(11) . . ? C7 P1 C1 103.57(11) . . ? N1 P1 S1 115.45(8) . . ? C7 P1 S1 110.93(9) . . ? C1 P1 S1 111.60(8) . . ? C19 N1 C16 115.0(2) . . ? C19 N1 P1 128.26(18) . . ? C16 N1 P1 113.81(17) . . ? C6 C1 C2 120.2(2) . . ? C6 C1 P1 118.04(18) . . ? C2 C1 P1 121.63(19) . . ? C3 C2 C1 117.1(2) . . ? C3 C2 Sn1 112.86(18) . . ? C1 C2 Sn1 129.99(18) . . ? C4 C3 C2 122.5(2) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C1 121.1(2) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C12 C7 C8 118.7(2) . . ? C12 C7 P1 121.19(19) . . ? C8 C7 P1 119.9(2) . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C7 C12 C11 120.4(3) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? Sn1 C13 H13A 109.5 . . ? Sn1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Sn1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Sn1 C14 H14A 109.5 . . ? Sn1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Sn1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Sn1 C15 H15A 109.5 . . ? Sn1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Sn1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 112.4(2) . . ? N1 C16 C18 112.6(3) . . ? C17 C16 C18 110.9(3) . . ? N1 C16 H16 106.8 . . ? C17 C16 H16 106.8 . . ? C18 C16 H16 106.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C21 112.3(3) . . ? N1 C19 C20 114.4(3) . . ? C21 C19 C20 112.6(3) . . ? N1 C19 H19 105.5 . . ? C21 C19 H19 105.5 . . ? C20 C19 H19 105.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 P1 N1 C19 -15.4(3) . . . . ? C1 P1 N1 C19 -126.1(2) . . . . ? S1 P1 N1 C19 110.1(2) . . . . ? C7 P1 N1 C16 -174.78(19) . . . . ? C1 P1 N1 C16 74.5(2) . . . . ? S1 P1 N1 C16 -49.3(2) . . . . ? N1 P1 C1 C6 20.3(2) . . . . ? C7 P1 C1 C6 -94.1(2) . . . . ? S1 P1 C1 C6 146.49(18) . . . . ? N1 P1 C1 C2 -164.35(19) . . . . ? C7 P1 C1 C2 81.2(2) . . . . ? S1 P1 C1 C2 -38.2(2) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? P1 C1 C2 C3 -176.22(19) . . . . ? C6 C1 C2 Sn1 176.87(19) . . . . ? P1 C1 C2 Sn1 1.6(3) . . . . ? C15 Sn1 C2 C3 126.95(19) . . . . ? C14 Sn1 C2 C3 -96.8(2) . . . . ? C13 Sn1 C2 C3 14.1(2) . . . . ? C15 Sn1 C2 C1 -51.0(3) . . . . ? C14 Sn1 C2 C1 85.3(2) . . . . ? C13 Sn1 C2 C1 -163.8(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? Sn1 C2 C3 C4 -178.0(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? P1 C1 C6 C5 176.8(2) . . . . ? N1 P1 C7 C12 -84.7(2) . . . . ? C1 P1 C7 C12 27.3(2) . . . . ? S1 P1 C7 C12 147.19(18) . . . . ? N1 P1 C7 C8 99.7(2) . . . . ? C1 P1 C7 C8 -148.2(2) . . . . ? S1 P1 C7 C8 -28.4(2) . . . . ? C12 C7 C8 C9 2.6(4) . . . . ? P1 C7 C8 C9 178.3(2) . . . . ? C7 C8 C9 C10 -1.4(4) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 1.0(4) . . . . ? C8 C7 C12 C11 -2.0(4) . . . . ? P1 C7 C12 C11 -177.63(19) . . . . ? C10 C11 C12 C7 0.2(4) . . . . ? C19 N1 C16 C17 64.5(3) . . . . ? P1 N1 C16 C17 -133.3(2) . . . . ? C19 N1 C16 C18 -61.7(3) . . . . ? P1 N1 C16 C18 100.5(3) . . . . ? C16 N1 C19 C21 -122.9(3) . . . . ? P1 N1 C19 C21 78.0(3) . . . . ? C16 N1 C19 C20 107.2(3) . . . . ? P1 N1 C19 C20 -52.0(4) . . . . ? # END of CIF