# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Wudl, Fred' _publ_contact_author_email wudl@chem.ucsb.edu _publ_section_title ; Electron injection barrier reduction for organic light-emitting devices by quinacridone derivatives ; loop_ _publ_author_name T.Pho A.Garcia P.Zalar T.-Q.Nguyen F.Wudl # Attachment '- Ph4PQPSO3.CIF' data_phom _database_code_depnum_ccdc_archive 'CCDC 776839' #TrackingRef '- Ph4PQPSO3.CIF' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C37 H35 N O6 P S' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour red _diffrn_ambient_temperature 293(2) _chemical_formula_weight 652.69 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' 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' N N 0.0061 0.0033 '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_int_tables_number 14 _chemical_absolute_configuration ? 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 7.3154(11) _cell_length_b 17.414(3) _cell_length_c 25.418(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.369(2) _cell_angle_gamma 90.00 _cell_volume 3235.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1372 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ccd area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25802 _diffrn_reflns_av_R_equivalents 0.1133 _diffrn_reflns_av_sigmaI/netI 0.1160 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 26.53 _reflns_number_total 6535 _reflns_number_gt 2693 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6535 _refine_ls_number_parameters 427 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1897 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.200 _refine_ls_shift/su_mean 0.005 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 0.3400(6) 0.7277(3) 0.41316(17) 0.0816(13) Uani 1 1 d . . . H1A H 0.2310 0.6982 0.4040 0.098 Uiso 1 1 calc R . . H1B H 0.3767 0.7160 0.4494 0.098 Uiso 1 1 calc R . . C2 C 0.2977(6) 0.8102(2) 0.40851(16) 0.0751(12) Uani 1 1 d . . . H2A H 0.2274 0.8190 0.3759 0.090 Uiso 1 1 calc R . . H2B H 0.4113 0.8387 0.4067 0.090 Uiso 1 1 calc R . . C3 C 0.1893(5) 0.8412(3) 0.45478(16) 0.0698(12) Uani 1 1 d . . . H3A H 0.0640 0.8231 0.4515 0.084 Uiso 1 1 calc R . . H3B H 0.2431 0.8220 0.4877 0.084 Uiso 1 1 calc R . . C4 C 0.0504(5) 0.9660(3) 0.43016(14) 0.0568(10) Uani 1 1 d . . . C5 C -0.1026(6) 0.9287(3) 0.40566(16) 0.0753(13) Uani 1 1 d . . . H5 H -0.1112 0.8754 0.4060 0.090 Uiso 1 1 calc R . . C6 C -0.2368(6) 0.9718(4) 0.38157(17) 0.0872(15) Uani 1 1 d . . . H6 H -0.3374 0.9469 0.3658 0.105 Uiso 1 1 calc R . . C7 C -0.2297(7) 1.0503(4) 0.37966(19) 0.0978(17) Uani 1 1 d . . . H7 H -0.3233 1.0780 0.3626 0.117 Uiso 1 1 calc R . . C8 C -0.0837(6) 1.0874(3) 0.40302(16) 0.0791(13) Uani 1 1 d . . . H8 H -0.0784 1.1408 0.4019 0.095 Uiso 1 1 calc R . . C9 C 0.0577(5) 1.0465(3) 0.42860(14) 0.0596(11) Uani 1 1 d . . . C10 C 0.2114(5) 1.0882(3) 0.45195(15) 0.0631(11) Uani 1 1 d . . . C11 C 0.3572(5) 1.0421(2) 0.47675(14) 0.0521(9) Uani 1 1 d . . . C12 C 0.3455(5) 0.9617(2) 0.47729(13) 0.0498(9) Uani 1 1 d . . . C13 C 0.5087(5) 1.0788(2) 0.49949(14) 0.0581(10) Uani 1 1 d . . . H13 H 0.5131 1.1322 0.4992 0.070 Uiso 1 1 calc R . . C14 C 0.2016(4) 0.4789(2) 0.34670(14) 0.0490(9) Uani 1 1 d . . . C15 C 0.0621(5) 0.5176(2) 0.31897(16) 0.0626(11) Uani 1 1 d . . . H15 H 0.0438 0.5102 0.2829 0.075 Uiso 1 1 calc R . . C16 C -0.0486(5) 0.5670(2) 0.3454(2) 0.0751(13) Uani 1 1 d . . . H16 H -0.1417 0.5933 0.3270 0.090 Uiso 1 1 calc R . . C17 C -0.0229(6) 0.5778(2) 0.3984(2) 0.0753(13) Uani 1 1 d . . . H17 H -0.0987 0.6114 0.4158 0.090 Uiso 1 1 calc R . . C18 C 0.1117(6) 0.5402(3) 0.42572(17) 0.0729(12) Uani 1 1 d . . . H18 H 0.1284 0.5482 0.4618 0.087 Uiso 1 1 calc R . . C19 C 0.2254(5) 0.4896(2) 0.40023(16) 0.0589(10) Uani 1 1 d . . . H19 H 0.3169 0.4633 0.4192 0.071 Uiso 1 1 calc R . . C20 C 0.4969(4) 0.3676(2) 0.35781(14) 0.0513(10) Uani 1 1 d . . . C21 C 0.4795(5) 0.2914(3) 0.37285(16) 0.0671(11) Uani 1 1 d . . . H21 H 0.3844 0.2614 0.3587 0.081 Uiso 1 1 calc R . . C22 C 0.6049(7) 0.2606(3) 0.40906(18) 0.0827(13) Uani 1 1 d . . . H22 H 0.5940 0.2095 0.4193 0.099 Uiso 1 1 calc R . . C23 C 0.7456(6) 0.3044(3) 0.43016(17) 0.0769(13) Uani 1 1 d . . . H23 H 0.8299 0.2828 0.4542 0.092 Uiso 1 1 calc R . . C24 C 0.7622(5) 0.3792(3) 0.41603(16) 0.0701(12) Uani 1 1 d . . . H24 H 0.8561 0.4092 0.4309 0.084 Uiso 1 1 calc R . . C25 C 0.6395(5) 0.4106(2) 0.37954(14) 0.0599(10) Uani 1 1 d . . . H25 H 0.6529 0.4615 0.3694 0.072 Uiso 1 1 calc R . . C26 C 0.1895(4) 0.3441(2) 0.28253(15) 0.0541(10) Uani 1 1 d . . . C27 C 0.0518(5) 0.3145(3) 0.31302(17) 0.0761(13) Uani 1 1 d . . . H27 H 0.0430 0.3304 0.3478 0.091 Uiso 1 1 calc R . . C28 C -0.0701(6) 0.2624(3) 0.2921(2) 0.0868(14) Uani 1 1 d . . . H28 H -0.1613 0.2429 0.3128 0.104 Uiso 1 1 calc R . . C29 C -0.0595(6) 0.2383(3) 0.2408(2) 0.0818(14) Uani 1 1 d . . . H29 H -0.1437 0.2030 0.2267 0.098 Uiso 1 1 calc R . . C30 C 0.0736(6) 0.2660(3) 0.21084(17) 0.0790(13) Uani 1 1 d . . . H30 H 0.0813 0.2496 0.1762 0.095 Uiso 1 1 calc R . . C31 C 0.1986(5) 0.3186(2) 0.23143(17) 0.0671(11) Uani 1 1 d . . . H31 H 0.2902 0.3371 0.2105 0.081 Uiso 1 1 calc R . . C32 C 0.4744(5) 0.4632(2) 0.26599(13) 0.0507(9) Uani 1 1 d . . . C33 C 0.5976(5) 0.4227(3) 0.23621(16) 0.0693(12) Uani 1 1 d . . . H33 H 0.6026 0.3694 0.2378 0.083 Uiso 1 1 calc R . . C34 C 0.7127(6) 0.4630(4) 0.20417(17) 0.0857(15) Uani 1 1 d . . . H34 H 0.7943 0.4363 0.1839 0.103 Uiso 1 1 calc R . . C35 C 0.7084(7) 0.5411(4) 0.20186(18) 0.0901(16) Uani 1 1 d . . . H35 H 0.7870 0.5671 0.1802 0.108 Uiso 1 1 calc R . . C36 C 0.5884(6) 0.5815(3) 0.23133(17) 0.0810(13) Uani 1 1 d . . . H36 H 0.5849 0.6349 0.2296 0.097 Uiso 1 1 calc R . . C37 C 0.4728(5) 0.5423(3) 0.26363(15) 0.0646(11) Uani 1 1 d . . . H37 H 0.3929 0.5697 0.2841 0.078 Uiso 1 1 calc R . . H51 H 0.560(8) 0.592(2) 0.4573(14) 0.150 Uiso 1 1 d D . . H52 H 0.574(8) 0.5243(10) 0.487(2) 0.150 Uiso 1 1 d D . . H61 H 0.184(7) 0.3490(11) 0.487(3) 0.150 Uiso 1 1 d D . . H62 H 0.250(5) 0.276(2) 0.500(2) 0.150 Uiso 1 1 d D . . N N 0.1909(4) 0.92501(19) 0.45527(12) 0.0573(8) Uani 1 1 d . . . O1 O 0.2198(4) 1.1590(2) 0.45058(14) 0.1055(11) Uani 1 1 d . . . O2 O 0.4597(4) 0.72189(18) 0.31908(11) 0.0900(9) Uani 1 1 d . . . O3 O 0.5367(4) 0.61861(17) 0.37885(11) 0.0856(9) Uani 1 1 d . . . O4 O 0.6773(4) 0.74340(18) 0.39134(12) 0.0985(10) Uani 1 1 d . . . O5 O 0.5947(6) 0.5688(2) 0.48327(14) 0.1242(13) Uani 1 1 d D . . O6 O 0.1680(6) 0.3044(4) 0.4928(4) 0.239(3) Uani 1 1 d D . . P P 0.34066(12) 0.41297(6) 0.31237(4) 0.0525(3) Uani 1 1 d . . . S S 0.51694(14) 0.70083(7) 0.37159(5) 0.0716(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.082(3) 0.071(4) 0.093(3) -0.002(3) 0.012(2) 0.007(3) C2 0.086(3) 0.062(3) 0.078(3) -0.006(2) 0.011(2) 0.010(2) C3 0.059(2) 0.070(3) 0.081(3) -0.006(2) 0.003(2) 0.001(2) C4 0.049(2) 0.075(3) 0.047(2) -0.007(2) 0.0074(18) 0.012(2) C5 0.063(3) 0.092(4) 0.070(3) -0.019(3) 0.001(2) 0.002(3) C6 0.056(3) 0.127(5) 0.077(3) -0.023(3) -0.011(2) 0.015(3) C7 0.079(4) 0.122(5) 0.091(4) -0.013(4) -0.013(3) 0.033(4) C8 0.065(3) 0.097(4) 0.075(3) 0.000(3) -0.011(2) 0.019(3) C9 0.056(3) 0.072(3) 0.050(2) -0.003(2) 0.0028(19) 0.014(2) C10 0.061(3) 0.060(3) 0.069(3) 0.002(3) 0.000(2) 0.008(3) C11 0.051(2) 0.051(3) 0.054(2) -0.002(2) 0.0020(18) 0.006(2) C12 0.045(2) 0.057(3) 0.047(2) -0.006(2) 0.0050(17) 0.000(2) C13 0.061(2) 0.050(3) 0.063(3) 0.000(2) 0.003(2) 0.003(2) C14 0.041(2) 0.054(3) 0.052(2) -0.0040(19) 0.0042(17) -0.0005(18) C15 0.048(2) 0.067(3) 0.072(3) -0.002(2) -0.005(2) 0.007(2) C16 0.049(3) 0.064(3) 0.112(4) 0.003(3) 0.004(3) 0.012(2) C17 0.059(3) 0.065(3) 0.104(4) -0.017(3) 0.020(3) 0.000(2) C18 0.069(3) 0.083(3) 0.068(3) -0.023(3) 0.019(2) -0.009(3) C19 0.051(2) 0.061(3) 0.064(3) -0.004(2) 0.009(2) -0.002(2) C20 0.037(2) 0.058(3) 0.060(3) -0.004(2) 0.0094(17) 0.0032(19) C21 0.051(2) 0.065(3) 0.086(3) 0.005(2) 0.003(2) 0.006(2) C22 0.076(3) 0.072(3) 0.100(4) 0.021(3) 0.008(3) 0.007(3) C23 0.055(3) 0.102(4) 0.073(3) 0.020(3) 0.001(2) 0.013(3) C24 0.045(2) 0.093(4) 0.072(3) 0.007(3) 0.000(2) -0.005(2) C25 0.044(2) 0.069(3) 0.067(3) 0.011(2) 0.0056(19) 0.004(2) C26 0.043(2) 0.059(3) 0.060(3) -0.005(2) 0.0053(18) 0.0067(19) C27 0.056(3) 0.094(4) 0.079(3) -0.021(3) 0.017(2) -0.017(2) C28 0.057(3) 0.103(4) 0.102(4) -0.017(3) 0.019(3) -0.018(3) C29 0.058(3) 0.089(4) 0.098(4) -0.028(3) -0.001(3) -0.010(2) C30 0.081(3) 0.085(4) 0.071(3) -0.020(3) 0.001(3) -0.012(3) C31 0.060(3) 0.073(3) 0.068(3) -0.009(2) 0.008(2) -0.008(2) C32 0.046(2) 0.058(3) 0.048(2) -0.003(2) 0.0002(17) 0.000(2) C33 0.054(2) 0.080(3) 0.074(3) -0.009(3) 0.009(2) 0.000(2) C34 0.059(3) 0.134(5) 0.065(3) -0.019(3) 0.019(2) -0.014(3) C35 0.089(4) 0.118(5) 0.064(3) -0.003(3) 0.016(3) -0.038(4) C36 0.090(3) 0.089(4) 0.064(3) 0.008(3) 0.002(3) -0.025(3) C37 0.061(3) 0.078(3) 0.056(3) 0.001(2) 0.007(2) -0.002(2) N 0.059(2) 0.052(2) 0.061(2) -0.0027(17) 0.0066(16) 0.0033(18) O1 0.098(2) 0.058(2) 0.157(3) 0.011(2) -0.039(2) 0.0109(19) O2 0.089(2) 0.108(3) 0.073(2) 0.0045(18) 0.0023(16) 0.0113(18) O3 0.094(2) 0.067(2) 0.096(2) -0.0016(17) 0.0047(17) 0.0077(17) O4 0.069(2) 0.107(3) 0.119(3) -0.021(2) 0.0066(17) -0.0142(18) O5 0.149(3) 0.127(4) 0.095(3) 0.026(2) -0.014(2) -0.034(3) O6 0.129(4) 0.168(5) 0.422(10) -0.154(7) 0.026(5) -0.012(4) P 0.0414(5) 0.0613(7) 0.0550(6) -0.0030(5) 0.0046(4) 0.0025(5) S 0.0600(7) 0.0826(10) 0.0727(9) -0.0037(7) 0.0091(6) 0.0066(6) _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 C2 1.473(5) . ? C1 S 1.768(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.543(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N 1.459(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N 1.385(4) . ? C4 C9 1.403(5) . ? C4 C5 1.417(5) . ? C5 C6 1.362(6) . ? C5 H5 0.9300 . ? C6 C7 1.369(6) . ? C6 H6 0.9300 . ? C7 C8 1.363(6) . ? C7 H7 0.9300 . ? C8 C9 1.395(5) . ? C8 H8 0.9300 . ? C9 C10 1.445(5) . ? C10 O1 1.237(4) . ? C10 C11 1.456(5) . ? C11 C13 1.385(5) . ? C11 C12 1.403(5) . ? C12 C13 1.390(5) 3_676 ? C12 N 1.396(4) . ? C13 C12 1.390(5) 3_676 ? C13 H13 0.9300 . ? C14 C19 1.377(5) . ? C14 C15 1.390(5) . ? C14 P 1.785(4) . ? C15 C16 1.376(5) . ? C15 H15 0.9300 . ? C16 C17 1.365(5) . ? C16 H16 0.9300 . ? C17 C18 1.351(5) . ? C17 H17 0.9300 . ? C18 C19 1.390(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C25 1.380(5) . ? C20 C21 1.389(5) . ? C20 P 1.776(4) . ? C21 C22 1.381(5) . ? C21 H21 0.9300 . ? C22 C23 1.373(6) . ? C22 H22 0.9300 . ? C23 C24 1.358(5) . ? C23 H23 0.9300 . ? C24 C25 1.377(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C31 1.377(5) . ? C26 C27 1.395(5) . ? C26 P 1.779(4) . ? C27 C28 1.365(5) . ? C27 H27 0.9300 . ? C28 C29 1.377(6) . ? C28 H28 0.9300 . ? C29 C30 1.350(6) . ? C29 H29 0.9300 . ? C30 C31 1.382(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C37 1.379(5) . ? C32 C33 1.393(5) . ? C32 P 1.791(4) . ? C33 C34 1.386(6) . ? C33 H33 0.9300 . ? C34 C35 1.361(6) . ? C34 H34 0.9300 . ? C35 C36 1.372(6) . ? C35 H35 0.9300 . ? C36 C37 1.383(5) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? O2 S 1.430(3) . ? O3 S 1.450(3) . ? O4 S 1.459(3) . ? O5 H51 0.806(10) . ? O5 H52 0.796(10) . ? O6 H61 0.801(10) . ? O6 H62 0.795(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 C2 C1 S 111.5(3) . . ? C2 C1 H1A 109.3 . . ? S C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? S C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 113.1(4) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N C3 C2 110.6(3) . . ? N C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N C4 C9 120.0(4) . . ? N C4 C5 121.6(4) . . ? C9 C4 C5 118.4(4) . . ? C6 C5 C4 119.1(5) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 122.6(5) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 119.2(5) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.9(5) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 119.7(4) . . ? C8 C9 C10 119.0(4) . . ? C4 C9 C10 121.3(4) . . ? O1 C10 C9 121.9(4) . . ? O1 C10 C11 121.7(4) . . ? C9 C10 C11 116.4(4) . . ? C13 C11 C12 120.3(3) . . ? C13 C11 C10 119.1(4) . . ? C12 C11 C10 120.6(4) . . ? C13 C12 N 122.2(4) 3_676 . ? C13 C12 C11 117.7(3) 3_676 . ? N C12 C11 120.1(3) . . ? C11 C13 C12 122.0(4) . 3_676 ? C11 C13 H13 119.0 . . ? C12 C13 H13 119.0 3_676 . ? C19 C14 C15 119.7(3) . . ? C19 C14 P 121.3(3) . . ? C15 C14 P 119.0(3) . . ? C16 C15 C14 119.3(4) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.5(4) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.4(4) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 119.6(4) . . ? C14 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C25 C20 C21 119.0(3) . . ? C25 C20 P 118.3(3) . . ? C21 C20 P 122.7(3) . . ? C22 C21 C20 119.3(4) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 120.7(4) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 120.3(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.7(4) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C20 121.1(4) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C31 C26 C27 118.0(4) . . ? C31 C26 P 124.5(3) . . ? C27 C26 P 117.5(3) . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 120.7(4) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 119.7(4) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 120.4(4) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C26 C31 C30 120.9(4) . . ? C26 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? C37 C32 C33 119.1(4) . . ? C37 C32 P 120.9(3) . . ? C33 C32 P 119.5(3) . . ? C34 C33 C32 119.0(4) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? C35 C34 C33 121.2(5) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C34 C35 C36 120.3(5) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C37 119.4(5) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C32 C37 C36 121.0(4) . . ? C32 C37 H37 119.5 . . ? C36 C37 H37 119.5 . . ? C4 N C12 121.5(3) . . ? C4 N C3 120.4(3) . . ? C12 N C3 117.9(3) . . ? H51 O5 H52 122(2) . . ? H61 O6 H62 122(2) . . ? C20 P C26 110.46(19) . . ? C20 P C14 109.41(17) . . ? C26 P C14 106.55(16) . . ? C20 P C32 106.92(17) . . ? C26 P C32 113.29(17) . . ? C14 P C32 110.20(18) . . ? O2 S O3 113.31(18) . . ? O2 S O4 113.0(2) . . ? O3 S O4 112.56(18) . . ? O2 S C1 107.2(2) . . ? O3 S C1 104.9(2) . . ? O4 S C1 104.9(2) . . ? 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 S C1 C2 C3 -162.6(3) . . . . ? C1 C2 C3 N 165.8(3) . . . . ? N C4 C5 C6 179.9(3) . . . . ? C9 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C7 0.5(6) . . . . ? C5 C6 C7 C8 -0.6(7) . . . . ? C6 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C4 0.3(6) . . . . ? C7 C8 C9 C10 178.8(4) . . . . ? N C4 C9 C8 179.7(3) . . . . ? C5 C4 C9 C8 -0.3(5) . . . . ? N C4 C9 C10 1.2(5) . . . . ? C5 C4 C9 C10 -178.8(3) . . . . ? C8 C9 C10 O1 1.1(6) . . . . ? C4 C9 C10 O1 179.6(4) . . . . ? C8 C9 C10 C11 -178.3(3) . . . . ? C4 C9 C10 C11 0.2(5) . . . . ? O1 C10 C11 C13 0.2(6) . . . . ? C9 C10 C11 C13 179.6(3) . . . . ? O1 C10 C11 C12 -179.3(4) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C13 C11 C12 C13 -0.9(5) . . . 3_676 ? C10 C11 C12 C13 178.5(3) . . . 3_676 ? C13 C11 C12 N 178.7(3) . . . . ? C10 C11 C12 N -1.8(5) . . . . ? C12 C11 C13 C12 1.0(6) . . . 3_676 ? C10 C11 C13 C12 -178.5(3) . . . 3_676 ? C19 C14 C15 C16 0.9(5) . . . . ? P C14 C15 C16 178.4(3) . . . . ? C14 C15 C16 C17 -0.3(6) . . . . ? C15 C16 C17 C18 0.0(6) . . . . ? C16 C17 C18 C19 -0.3(6) . . . . ? C15 C14 C19 C18 -1.2(5) . . . . ? P C14 C19 C18 -178.6(3) . . . . ? C17 C18 C19 C14 0.9(6) . . . . ? C25 C20 C21 C22 0.0(5) . . . . ? P C20 C21 C22 -179.0(3) . . . . ? C20 C21 C22 C23 0.0(6) . . . . ? C21 C22 C23 C24 0.7(7) . . . . ? C22 C23 C24 C25 -1.4(6) . . . . ? C23 C24 C25 C20 1.4(6) . . . . ? C21 C20 C25 C24 -0.7(5) . . . . ? P C20 C25 C24 178.3(3) . . . . ? C31 C26 C27 C28 -0.5(6) . . . . ? P C26 C27 C28 179.0(3) . . . . ? C26 C27 C28 C29 -0.1(7) . . . . ? C27 C28 C29 C30 0.5(7) . . . . ? C28 C29 C30 C31 -0.3(7) . . . . ? C27 C26 C31 C30 0.8(6) . . . . ? P C26 C31 C30 -178.7(3) . . . . ? C29 C30 C31 C26 -0.4(7) . . . . ? C37 C32 C33 C34 -1.3(5) . . . . ? P C32 C33 C34 -173.9(3) . . . . ? C32 C33 C34 C35 0.7(6) . . . . ? C33 C34 C35 C36 -0.2(7) . . . . ? C34 C35 C36 C37 0.4(7) . . . . ? C33 C32 C37 C36 1.5(5) . . . . ? P C32 C37 C36 174.0(3) . . . . ? C35 C36 C37 C32 -1.1(6) . . . . ? C9 C4 N C12 -3.0(5) . . . . ? C5 C4 N C12 177.0(3) . . . . ? C9 C4 N C3 -176.8(3) . . . . ? C5 C4 N C3 3.2(5) . . . . ? C13 C12 N C4 -177.0(3) 3_676 . . . ? C11 C12 N C4 3.3(5) . . . . ? C13 C12 N C3 -3.0(5) 3_676 . . . ? C11 C12 N C3 177.3(3) . . . . ? C2 C3 N C4 93.3(4) . . . . ? C2 C3 N C12 -80.8(4) . . . . ? C25 C20 P C26 171.6(3) . . . . ? C21 C20 P C26 -9.4(4) . . . . ? C25 C20 P C14 -71.4(3) . . . . ? C21 C20 P C14 107.6(3) . . . . ? C25 C20 P C32 48.0(3) . . . . ? C21 C20 P C32 -133.1(3) . . . . ? C31 C26 P C20 -106.3(3) . . . . ? C27 C26 P C20 74.1(3) . . . . ? C31 C26 P C14 134.9(3) . . . . ? C27 C26 P C14 -44.6(3) . . . . ? C31 C26 P C32 13.6(4) . . . . ? C27 C26 P C32 -165.9(3) . . . . ? C19 C14 P C20 1.1(3) . . . . ? C15 C14 P C20 -176.3(3) . . . . ? C19 C14 P C26 120.5(3) . . . . ? C15 C14 P C26 -56.9(3) . . . . ? C19 C14 P C32 -116.2(3) . . . . ? C15 C14 P C32 66.4(3) . . . . ? C37 C32 P C20 -113.5(3) . . . . ? C33 C32 P C20 59.0(3) . . . . ? C37 C32 P C26 124.6(3) . . . . ? C33 C32 P C26 -62.9(3) . . . . ? C37 C32 P C14 5.4(3) . . . . ? C33 C32 P C14 177.8(3) . . . . ? C2 C1 S O2 -56.8(4) . . . . ? C2 C1 S O3 -177.6(3) . . . . ? C2 C1 S O4 63.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.53 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.293 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.059