Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 222 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Aaron Odom' 'Sanjukta Banerjee' _publ_contact_author_name 'Aaron Odom' _publ_contact_author_address ; Department of Chemistry Michigan State University East Lansing East Lansing MI 48824 1322 UNITED STATES OF AMERICA ; _publ_contact_author_email ODOM@CHEMISTRY.MSU.EDU _publ_section_title ; ; # Attachment 'odomsb920_0m.cif' data_odomsb920_0m _database_code_depnum_ccdc_archive 'CCDC 670307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 I N3 O P2 S V' _chemical_formula_weight 613.33 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 10.8685(2) _cell_length_b 18.3385(3) _cell_length_c 26.2108(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5224.13(16) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9828 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.72 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 1.782 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67170 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.90 _reflns_number_total 6199 _reflns_number_gt 4577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+3.9062P] 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 6199 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.009 _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 V1 V 0.77653(4) 0.41414(2) 0.350937(17) 0.02198(10) Uani 1 1 d . . . S1 S 0.80298(6) 0.52589(4) 0.30940(3) 0.02942(16) Uani 1 1 d . . . P1 P 0.73869(7) 0.49552(4) 0.42621(3) 0.02898(17) Uani 1 1 d . . . P2 P 0.77508(7) 0.33039(4) 0.42658(3) 0.02935(17) Uani 1 1 d . . . O1 O 0.80641(16) 0.32564(9) 0.31471(7) 0.0259(4) Uani 1 1 d . . . N1 N 0.62310(19) 0.41253(11) 0.33880(8) 0.0252(5) Uani 1 1 d . . . N2 N 0.5130(2) 0.40825(13) 0.32033(10) 0.0358(6) Uani 1 1 d . . . N3 N 0.97491(19) 0.42232(11) 0.34973(8) 0.0234(5) Uani 1 1 d . . . C1 C 0.9483(2) 0.54943(14) 0.33419(10) 0.0259(6) Uani 1 1 d . . . C2 C 0.9885(3) 0.62159(14) 0.33706(11) 0.0329(7) Uani 1 1 d . . . H2 H 0.9410 0.6587 0.3230 0.039 Uiso 1 1 calc R . . C3 C 1.0986(3) 0.63811(15) 0.36063(11) 0.0368(7) Uani 1 1 d . . . H3 H 1.1247 0.6863 0.3626 0.044 Uiso 1 1 calc R . . C4 C 1.1702(3) 0.58333(15) 0.38138(11) 0.0333(7) Uani 1 1 d . . . H4 H 1.2438 0.5949 0.3975 0.040 Uiso 1 1 calc R . . C5 C 1.1327(2) 0.51107(14) 0.37819(10) 0.0282(6) Uani 1 1 d . . . H5 H 1.1812 0.4742 0.3919 0.034 Uiso 1 1 calc R . . C6 C 1.0222(2) 0.49448(13) 0.35437(10) 0.0242(6) Uani 1 1 d . . . C7 C 1.0530(2) 0.37097(14) 0.33920(10) 0.0251(6) Uani 1 1 d . . . H7 H 1.1363 0.3824 0.3410 0.030 Uiso 1 1 calc R . . C8 C 1.0208(2) 0.29776(13) 0.32496(10) 0.0245(6) Uani 1 1 d . . . C9 C 1.1147(3) 0.24576(14) 0.31884(11) 0.0326(7) Uani 1 1 d . . . H9 H 1.1953 0.2584 0.3267 0.039 Uiso 1 1 calc R . . C10 C 1.0898(3) 0.17687(14) 0.30148(11) 0.0346(7) Uani 1 1 d . . . H10 H 1.1528 0.1429 0.2980 0.042 Uiso 1 1 calc R . . C11 C 0.9693(3) 0.15835(14) 0.28906(11) 0.0319(7) Uani 1 1 d . . . H11 H 0.9521 0.1117 0.2772 0.038 Uiso 1 1 calc R . . C12 C 0.8754(3) 0.20796(14) 0.29406(10) 0.0288(6) Uani 1 1 d . . . H12 H 0.7955 0.1946 0.2854 0.035 Uiso 1 1 calc R . . C13 C 0.8990(2) 0.27856(14) 0.31214(9) 0.0240(6) Uani 1 1 d . . . C14 C 0.4677(3) 0.33678(18) 0.30518(13) 0.0505(9) Uani 1 1 d . . . H14A H 0.5348 0.3080 0.2924 0.076 Uiso 1 1 calc R . . H14B H 0.4068 0.3423 0.2790 0.076 Uiso 1 1 calc R . . H14C H 0.4317 0.3129 0.3341 0.076 Uiso 1 1 calc R . . C15 C 0.4278(3) 0.46827(18) 0.32633(15) 0.0543(10) Uani 1 1 d . . . H15A H 0.3815 0.4618 0.3572 0.081 Uiso 1 1 calc R . . H15B H 0.3726 0.4695 0.2977 0.081 Uiso 1 1 calc R . . H15C H 0.4727 0.5133 0.3280 0.081 Uiso 1 1 calc R . . C16 C 0.6605(4) 0.44275(18) 0.47568(13) 0.0566(10) Uani 1 1 d . . . H16A H 0.6554 0.4713 0.5068 0.068 Uiso 1 1 calc R . . H16B H 0.5775 0.4313 0.4647 0.068 Uiso 1 1 calc R . . C17 C 0.7287(4) 0.37455(18) 0.48571(13) 0.0650(12) Uani 1 1 d . . . H17A H 0.6772 0.3416 0.5052 0.078 Uiso 1 1 calc R . . H17B H 0.8012 0.3854 0.5059 0.078 Uiso 1 1 calc R . . C18 C 0.6357(3) 0.57160(18) 0.41766(14) 0.0567(10) Uani 1 1 d . . . H18A H 0.6279 0.5977 0.4492 0.085 Uiso 1 1 calc R . . H18B H 0.5564 0.5540 0.4072 0.085 Uiso 1 1 calc R . . H18C H 0.6679 0.6036 0.3919 0.085 Uiso 1 1 calc R . . C19 C 0.8688(3) 0.5351(2) 0.45809(12) 0.0492(9) Uani 1 1 d . . . H19A H 0.9032 0.5729 0.4372 0.074 Uiso 1 1 calc R . . H19B H 0.9298 0.4981 0.4640 0.074 Uiso 1 1 calc R . . H19C H 0.8430 0.5553 0.4901 0.074 Uiso 1 1 calc R . . C20 C 0.6690(3) 0.25577(16) 0.41888(13) 0.0428(8) Uani 1 1 d . . . H20A H 0.6735 0.2244 0.4481 0.064 Uiso 1 1 calc R . . H20B H 0.6900 0.2286 0.3888 0.064 Uiso 1 1 calc R . . H20C H 0.5869 0.2745 0.4156 0.064 Uiso 1 1 calc R . . C21 C 0.9183(3) 0.2858(2) 0.44402(13) 0.0519(9) Uani 1 1 d . . . H21A H 0.9072 0.2596 0.4754 0.078 Uiso 1 1 calc R . . H21B H 0.9816 0.3218 0.4483 0.078 Uiso 1 1 calc R . . H21C H 0.9418 0.2524 0.4176 0.078 Uiso 1 1 calc R . . I1 I 0.192028(18) 0.837920(10) 0.439444(7) 0.03629(7) 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 V1 0.0192(2) 0.0242(2) 0.0225(2) 0.00009(19) 0.00050(18) 0.00138(18) S1 0.0265(4) 0.0291(3) 0.0327(4) 0.0072(3) -0.0002(3) 0.0038(3) P1 0.0312(4) 0.0285(4) 0.0273(4) -0.0017(3) 0.0040(3) 0.0040(3) P2 0.0359(4) 0.0273(4) 0.0249(4) 0.0023(3) 0.0013(3) -0.0045(3) O1 0.0207(9) 0.0292(10) 0.0279(10) -0.0042(8) -0.0002(8) 0.0018(8) N1 0.0229(12) 0.0292(12) 0.0233(12) 0.0011(10) 0.0014(9) 0.0006(10) N2 0.0188(12) 0.0444(15) 0.0443(16) -0.0029(12) -0.0047(11) -0.0012(11) N3 0.0220(11) 0.0228(11) 0.0252(12) 0.0008(9) -0.0004(9) 0.0000(9) C1 0.0246(14) 0.0287(14) 0.0243(14) 0.0014(11) 0.0067(11) 0.0014(11) C2 0.0390(17) 0.0245(14) 0.0352(17) 0.0029(13) 0.0065(14) 0.0027(12) C3 0.0455(19) 0.0245(14) 0.0405(18) -0.0019(13) 0.0089(15) -0.0094(13) C4 0.0294(16) 0.0360(16) 0.0345(17) -0.0042(13) 0.0013(13) -0.0058(13) C5 0.0253(15) 0.0277(14) 0.0318(16) -0.0011(12) 0.0046(12) 0.0000(11) C6 0.0249(14) 0.0216(13) 0.0261(15) -0.0022(11) 0.0054(11) -0.0016(11) C7 0.0213(14) 0.0282(14) 0.0258(15) 0.0013(12) -0.0029(11) 0.0000(11) C8 0.0233(14) 0.0231(13) 0.0271(15) 0.0000(11) -0.0005(11) 0.0007(11) C9 0.0264(15) 0.0289(14) 0.0424(18) 0.0016(13) -0.0008(13) 0.0042(12) C10 0.0391(17) 0.0251(15) 0.0397(18) -0.0009(12) 0.0014(14) 0.0087(13) C11 0.0424(18) 0.0227(14) 0.0306(16) -0.0020(12) 0.0044(13) -0.0021(13) C12 0.0313(16) 0.0297(15) 0.0254(15) -0.0024(12) 0.0029(12) -0.0049(12) C13 0.0263(14) 0.0259(13) 0.0197(14) 0.0024(11) 0.0025(11) 0.0014(11) C14 0.044(2) 0.067(2) 0.041(2) -0.0222(17) -0.0003(15) -0.0187(17) C15 0.0314(18) 0.055(2) 0.076(3) 0.0229(19) -0.0116(18) 0.0073(16) C16 0.074(3) 0.049(2) 0.047(2) -0.0074(17) 0.0318(19) -0.0054(18) C17 0.130(4) 0.0350(18) 0.0300(19) 0.0003(15) 0.027(2) -0.002(2) C18 0.063(2) 0.057(2) 0.050(2) -0.0208(18) -0.0113(19) 0.0314(19) C19 0.0367(19) 0.074(2) 0.0366(19) -0.0205(18) -0.0002(15) -0.0004(17) C20 0.0420(19) 0.0350(16) 0.051(2) 0.0046(15) 0.0001(16) -0.0081(14) C21 0.0398(19) 0.070(2) 0.046(2) 0.0336(18) -0.0064(16) -0.0070(17) I1 0.04090(12) 0.04028(11) 0.02768(11) 0.00272(9) -0.00018(9) -0.01063(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V1 N1 1.698(2) . ? V1 O1 1.9081(17) . ? V1 N3 2.162(2) . ? V1 S1 2.3383(8) . ? V1 P2 2.5079(8) . ? V1 P1 2.5078(8) . ? S1 C1 1.761(3) . ? P1 C19 1.796(3) . ? P1 C18 1.803(3) . ? P1 C16 1.827(3) . ? P2 C20 1.801(3) . ? P2 C21 1.817(3) . ? P2 C17 1.820(3) . ? O1 C13 1.328(3) . ? N1 N2 1.293(3) . ? N2 C15 1.447(4) . ? N2 C14 1.455(4) . ? N3 C7 1.298(3) . ? N3 C6 1.425(3) . ? C1 C6 1.393(4) . ? C1 C2 1.396(4) . ? C2 C3 1.380(4) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C5 C6 1.387(4) . ? C5 H5 0.9300 . ? C7 C8 1.437(3) . ? C7 H7 0.9300 . ? C8 C9 1.405(3) . ? C8 C13 1.411(4) . ? C9 C10 1.370(4) . ? C9 H9 0.9300 . ? C10 C11 1.392(4) . ? C10 H10 0.9300 . ? C11 C12 1.373(4) . ? C11 H11 0.9300 . ? C12 C13 1.402(4) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.477(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 V1 O1 93.40(9) . . ? N1 V1 N3 167.99(9) . . ? O1 V1 N3 83.22(8) . . ? N1 V1 S1 92.79(8) . . ? O1 V1 S1 119.53(6) . . ? N3 V1 S1 79.03(6) . . ? N1 V1 P2 97.55(8) . . ? O1 V1 P2 82.74(6) . . ? N3 V1 P2 93.46(6) . . ? S1 V1 P2 154.89(3) . . ? N1 V1 P1 89.81(8) . . ? O1 V1 P1 157.76(6) . . ? N3 V1 P1 97.69(6) . . ? S1 V1 P1 82.23(3) . . ? P2 V1 P1 75.02(3) . . ? C1 S1 V1 98.82(9) . . ? C19 P1 C18 103.56(17) . . ? C19 P1 C16 104.47(18) . . ? C18 P1 C16 102.08(18) . . ? C19 P1 V1 118.51(11) . . ? C18 P1 V1 117.69(11) . . ? C16 P1 V1 108.62(11) . . ? C20 P2 C21 103.56(16) . . ? C20 P2 C17 104.85(17) . . ? C21 P2 C17 102.90(19) . . ? C20 P2 V1 112.39(11) . . ? C21 P2 V1 117.99(10) . . ? C17 P2 V1 113.73(11) . . ? C13 O1 V1 135.01(16) . . ? N2 N1 V1 168.5(2) . . ? N1 N2 C15 120.3(2) . . ? N1 N2 C14 118.0(2) . . ? C15 N2 C14 119.9(2) . . ? C7 N3 C6 117.1(2) . . ? C7 N3 V1 127.25(17) . . ? C6 N3 V1 115.05(16) . . ? C6 C1 C2 119.0(2) . . ? C6 C1 S1 118.70(19) . . ? C2 C1 S1 122.2(2) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.8(2) . . ? C5 C6 N3 123.7(2) . . ? C1 C6 N3 115.5(2) . . ? N3 C7 C8 125.0(2) . . ? N3 C7 H7 117.5 . . ? C8 C7 H7 117.5 . . ? C9 C8 C13 119.0(2) . . ? C9 C8 C7 119.1(2) . . ? C13 C8 C7 121.6(2) . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.2(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? O1 C13 C12 118.6(2) . . ? O1 C13 C8 122.5(2) . . ? C12 C13 C8 118.9(2) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 P1 110.0(2) . . ? C17 C16 H16A 109.7 . . ? P1 C16 H16A 109.7 . . ? C17 C16 H16B 109.7 . . ? P1 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C16 C17 P2 111.4(2) . . ? C16 C17 H17A 109.4 . . ? P2 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? P2 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? P1 C18 H18A 109.5 . . ? P1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? P1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? P1 C19 H19A 109.5 . . ? P1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? P1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? P2 C20 H20A 109.5 . . ? P2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? P2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? P2 C21 H21A 109.5 . . ? P2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? P2 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 N1 V1 S1 C1 163.52(11) . . . . ? O1 V1 S1 C1 -100.99(11) . . . . ? N3 V1 S1 C1 -25.34(11) . . . . ? P2 V1 S1 C1 49.06(12) . . . . ? P1 V1 S1 C1 74.10(9) . . . . ? N1 V1 P1 C19 -171.61(16) . . . . ? O1 V1 P1 C19 89.9(2) . . . . ? N3 V1 P1 C19 -1.02(15) . . . . ? S1 V1 P1 C19 -78.77(14) . . . . ? P2 V1 P1 C19 90.52(14) . . . . ? N1 V1 P1 C18 -45.71(17) . . . . ? O1 V1 P1 C18 -144.2(2) . . . . ? N3 V1 P1 C18 124.87(16) . . . . ? S1 V1 P1 C18 47.13(15) . . . . ? P2 V1 P1 C18 -143.58(16) . . . . ? N1 V1 P1 C16 69.51(16) . . . . ? O1 V1 P1 C16 -29.0(2) . . . . ? N3 V1 P1 C16 -119.90(15) . . . . ? S1 V1 P1 C16 162.35(14) . . . . ? P2 V1 P1 C16 -28.36(14) . . . . ? N1 V1 P2 C20 38.93(14) . . . . ? O1 V1 P2 C20 -53.56(13) . . . . ? N3 V1 P2 C20 -136.27(13) . . . . ? S1 V1 P2 C20 152.41(13) . . . . ? P1 V1 P2 C20 126.69(12) . . . . ? N1 V1 P2 C21 159.34(16) . . . . ? O1 V1 P2 C21 66.85(15) . . . . ? N3 V1 P2 C21 -15.86(15) . . . . ? S1 V1 P2 C21 -87.18(16) . . . . ? P1 V1 P2 C21 -112.90(14) . . . . ? N1 V1 P2 C17 -80.01(18) . . . . ? O1 V1 P2 C17 -172.49(18) . . . . ? N3 V1 P2 C17 104.80(18) . . . . ? S1 V1 P2 C17 33.48(19) . . . . ? P1 V1 P2 C17 7.76(17) . . . . ? N1 V1 O1 C13 -165.1(2) . . . . ? N3 V1 O1 C13 26.5(2) . . . . ? S1 V1 O1 C13 99.8(2) . . . . ? P2 V1 O1 C13 -67.9(2) . . . . ? P1 V1 O1 C13 -67.3(3) . . . . ? O1 V1 N1 N2 -45.9(10) . . . . ? N3 V1 N1 N2 27.3(13) . . . . ? S1 V1 N1 N2 74.0(10) . . . . ? P2 V1 N1 N2 -129.0(10) . . . . ? P1 V1 N1 N2 156.2(10) . . . . ? V1 N1 N2 C15 -125.5(9) . . . . ? V1 N1 N2 C14 69.5(11) . . . . ? N1 V1 N3 C7 -89.4(5) . . . . ? O1 V1 N3 C7 -15.1(2) . . . . ? S1 V1 N3 C7 -137.0(2) . . . . ? P2 V1 N3 C7 67.1(2) . . . . ? P1 V1 N3 C7 142.5(2) . . . . ? N1 V1 N3 C6 81.6(5) . . . . ? O1 V1 N3 C6 155.85(18) . . . . ? S1 V1 N3 C6 33.94(16) . . . . ? P2 V1 N3 C6 -121.89(17) . . . . ? P1 V1 N3 C6 -46.56(17) . . . . ? V1 S1 C1 C6 20.3(2) . . . . ? V1 S1 C1 C2 -155.8(2) . . . . ? C6 C1 C2 C3 -1.5(4) . . . . ? S1 C1 C2 C3 174.6(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? C4 C5 C6 N3 -179.1(2) . . . . ? C2 C1 C6 C5 1.7(4) . . . . ? S1 C1 C6 C5 -174.5(2) . . . . ? C2 C1 C6 N3 -179.7(2) . . . . ? S1 C1 C6 N3 4.1(3) . . . . ? C7 N3 C6 C5 -40.4(4) . . . . ? V1 N3 C6 C5 147.7(2) . . . . ? C7 N3 C6 C1 141.1(2) . . . . ? V1 N3 C6 C1 -30.8(3) . . . . ? C6 N3 C7 C8 -169.3(2) . . . . ? V1 N3 C7 C8 1.5(4) . . . . ? N3 C7 C8 C9 -174.6(3) . . . . ? N3 C7 C8 C13 11.7(4) . . . . ? C13 C8 C9 C10 -1.0(4) . . . . ? C7 C8 C9 C10 -174.9(3) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? V1 O1 C13 C12 160.11(19) . . . . ? V1 O1 C13 C8 -22.5(4) . . . . ? C11 C12 C13 O1 177.7(2) . . . . ? C11 C12 C13 C8 0.2(4) . . . . ? C9 C8 C13 O1 -176.9(2) . . . . ? C7 C8 C13 O1 -3.2(4) . . . . ? C9 C8 C13 C12 0.5(4) . . . . ? C7 C8 C13 C12 174.2(2) . . . . ? C19 P1 C16 C17 -75.9(3) . . . . ? C18 P1 C16 C17 176.4(3) . . . . ? V1 P1 C16 C17 51.5(3) . . . . ? P1 C16 C17 P2 -44.8(4) . . . . ? C20 P2 C17 C16 -103.4(3) . . . . ? C21 P2 C17 C16 148.6(3) . . . . ? V1 P2 C17 C16 19.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.689 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.083