# Electronic Supplementary Material (ESI) for Chemical Communications # 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_1PPh _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-DAC=PPh _chemical_melting_point ? _chemical_formula_moiety {(C9H11)2-C6H6N2O2-P(C6H5)} _chemical_formula_sum 'C30 H33 N2 O2 P' _chemical_formula_weight 484.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.4029(8) _cell_length_b 14.4398(8) _cell_length_c 25.9117(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5389.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _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 43779 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4733 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0890P)^2^+1.4307P] 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 4733 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.87183(5) 0.18645(5) 0.69713(3) 0.0553(2) Uani 1 1 d . . . N1 N 0.96386(13) 0.03111(12) 0.71697(7) 0.0431(5) Uani 1 1 d . . . O1 O 1.01157(16) -0.11202(12) 0.74161(8) 0.0709(6) Uani 1 1 d . . . N2 N 1.00365(13) 0.09057(13) 0.63422(7) 0.0431(5) Uani 1 1 d . . . O2 O 1.10299(13) 0.00520(13) 0.58560(7) 0.0642(5) Uani 1 1 d . . . C2 C 0.94879(16) 0.10086(15) 0.67911(8) 0.0413(5) Uani 1 1 d . . . C3 C 1.00071(17) -0.05600(16) 0.70699(10) 0.0486(6) Uani 1 1 d . . . C4 C 1.02125(18) -0.07828(17) 0.65109(10) 0.0512(6) Uani 1 1 d . . . C5 C 1.04791(17) 0.00795(17) 0.62130(10) 0.0478(6) Uani 1 1 d . . . C6 C 1.0975(2) -0.15209(19) 0.64741(13) 0.0723(8) Uani 1 1 d . . . H6A H 1.1539 -0.1284 0.6621 0.108 Uiso 1 1 calc R . . H6B H 1.1078 -0.1677 0.6119 0.108 Uiso 1 1 calc R . . H6C H 1.0785 -0.2064 0.6660 0.108 Uiso 1 1 calc R . . C7 C 0.9299(2) -0.1150(2) 0.62673(12) 0.0692(8) Uani 1 1 d . . . H7A H 0.8827 -0.0682 0.6291 0.104 Uiso 1 1 calc R . . H7B H 0.9100 -0.1694 0.6449 0.104 Uiso 1 1 calc R . . H7C H 0.9405 -0.1300 0.5911 0.104 Uiso 1 1 calc R . . C11 C 0.92823(18) 0.04613(16) 0.76903(9) 0.0457(6) Uani 1 1 d . . . C12 C 0.98418(18) 0.09187(16) 0.80509(9) 0.0485(6) Uani 1 1 d . . . C13 C 0.9477(2) 0.10542(17) 0.85397(10) 0.0545(7) Uani 1 1 d . . . H13A H 0.9840 0.1353 0.8785 0.065 Uiso 1 1 calc R . . C14 C 0.8595(2) 0.07643(19) 0.86794(10) 0.0592(7) Uani 1 1 d . . . C15 C 0.8079(2) 0.02872(19) 0.83140(10) 0.0619(7) Uani 1 1 d . . . H15A H 0.7490 0.0078 0.8404 0.074 Uiso 1 1 calc R . . C16 C 0.84060(19) 0.01084(17) 0.78174(10) 0.0517(6) Uani 1 1 d . . . C17 C 1.0796(2) 0.1267(2) 0.79195(12) 0.0695(8) Uani 1 1 d . . . H17A H 1.1164 0.1300 0.8228 0.104 Uiso 1 1 calc R . . H17B H 1.0749 0.1872 0.7768 0.104 Uiso 1 1 calc R . . H17C H 1.1084 0.0852 0.7679 0.104 Uiso 1 1 calc R . . C18 C 0.8198(3) 0.0990(3) 0.92101(11) 0.0871(10) Uani 1 1 d . . . H18A H 0.7757 0.0523 0.9307 0.131 Uiso 1 1 calc R . . H18B H 0.7896 0.1582 0.9199 0.131 Uiso 1 1 calc R . . H18C H 0.8692 0.1007 0.9459 0.131 Uiso 1 1 calc R . . C19 C 0.7840(2) -0.0444(2) 0.74367(11) 0.0659(8) Uani 1 1 d . . . H19A H 0.7236 -0.0562 0.7579 0.099 Uiso 1 1 calc R . . H19B H 0.8146 -0.1021 0.7367 0.099 Uiso 1 1 calc R . . H19C H 0.7777 -0.0099 0.7122 0.099 Uiso 1 1 calc R . . C21 C 1.02312(17) 0.16817(16) 0.59977(9) 0.0460(6) Uani 1 1 d . . . C22 C 1.08856(17) 0.23470(17) 0.61440(10) 0.0508(6) Uani 1 1 d . . . C23 C 1.1094(2) 0.30452(19) 0.57866(12) 0.0628(7) Uani 1 1 d . . . H23A H 1.1520 0.3500 0.5878 0.075 Uiso 1 1 calc R . . C24 C 1.0689(2) 0.3084(2) 0.53028(11) 0.0644(8) Uani 1 1 d . . . C25 C 1.0052(2) 0.2408(2) 0.51756(10) 0.0630(8) Uani 1 1 d . . . H25A H 0.9774 0.2431 0.4852 0.076 Uiso 1 1 calc R . . C26 C 0.98070(18) 0.16908(19) 0.55112(9) 0.0525(6) Uani 1 1 d . . . C27 C 1.1353(2) 0.2334(2) 0.66616(11) 0.0679(8) Uani 1 1 d . . . H27A H 1.1489 0.1707 0.6757 0.102 Uiso 1 1 calc R . . H27B H 1.0950 0.2606 0.6915 0.102 Uiso 1 1 calc R . . H27C H 1.1920 0.2683 0.6644 0.102 Uiso 1 1 calc R . . C28 C 1.0937(3) 0.3853(2) 0.49296(15) 0.0979(12) Uani 1 1 d . . . H28A H 1.0892 0.3627 0.4582 0.147 Uiso 1 1 calc R . . H28B H 1.1560 0.4058 0.4995 0.147 Uiso 1 1 calc R . . H28C H 1.0515 0.4362 0.4976 0.147 Uiso 1 1 calc R . . C29 C 0.9129(2) 0.0953(2) 0.53480(11) 0.0667(8) Uani 1 1 d . . . H29A H 0.8788 0.1162 0.5052 0.100 Uiso 1 1 calc R . . H29B H 0.8705 0.0829 0.5626 0.100 Uiso 1 1 calc R . . H29C H 0.9461 0.0397 0.5263 0.100 Uiso 1 1 calc R . . C31 C 0.85239(17) 0.26299(17) 0.64128(9) 0.0478(6) Uani 1 1 d . . . C32 C 0.8916(2) 0.35127(18) 0.64014(10) 0.0575(7) Uani 1 1 d . . . H32A H 0.9347 0.3683 0.6651 0.069 Uiso 1 1 calc R . . C33 C 0.8665(2) 0.4138(2) 0.60194(11) 0.0694(8) Uani 1 1 d . . . H33A H 0.8938 0.4721 0.6012 0.083 Uiso 1 1 calc R . . C34 C 0.8023(2) 0.3906(2) 0.56540(11) 0.0676(8) Uani 1 1 d . . . H34A H 0.7862 0.4330 0.5399 0.081 Uiso 1 1 calc R . . C35 C 0.7614(2) 0.3045(2) 0.56641(11) 0.0657(8) Uani 1 1 d . . . H35A H 0.7179 0.2886 0.5415 0.079 Uiso 1 1 calc R . . C36 C 0.78525(18) 0.24108(19) 0.60479(10) 0.0566(7) Uani 1 1 d . . . H36A H 0.7560 0.1837 0.6060 0.068 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 0.0659(5) 0.0525(4) 0.0477(4) 0.0105(3) 0.0127(3) 0.0175(3) N1 0.0475(11) 0.0387(10) 0.0431(11) 0.0028(8) -0.0030(9) 0.0020(9) O1 0.1003(16) 0.0476(10) 0.0647(12) 0.0064(9) -0.0119(11) 0.0173(10) N2 0.0466(11) 0.0410(10) 0.0417(11) -0.0052(9) 0.0025(9) 0.0009(9) O2 0.0656(12) 0.0653(12) 0.0618(12) -0.0154(10) 0.0116(10) 0.0075(10) C2 0.0452(13) 0.0419(12) 0.0369(12) 0.0004(10) -0.0030(10) -0.0021(10) C3 0.0503(14) 0.0385(13) 0.0569(15) -0.0027(12) -0.0107(12) -0.0002(11) C4 0.0565(15) 0.0413(12) 0.0558(15) -0.0122(12) -0.0101(12) -0.0006(12) C5 0.0443(14) 0.0487(14) 0.0505(14) -0.0126(12) -0.0046(12) 0.0005(11) C6 0.077(2) 0.0486(15) 0.092(2) -0.0152(15) -0.0043(17) 0.0109(15) C7 0.0695(19) 0.0659(18) 0.0722(19) -0.0152(15) -0.0153(15) -0.0161(15) C11 0.0550(15) 0.0411(12) 0.0410(13) 0.0070(10) -0.0032(11) 0.0064(11) C12 0.0569(16) 0.0431(13) 0.0454(14) 0.0041(11) -0.0067(12) 0.0063(11) C13 0.0688(18) 0.0488(14) 0.0458(14) 0.0009(11) -0.0088(13) 0.0077(13) C14 0.0732(19) 0.0585(16) 0.0458(15) 0.0084(13) 0.0052(13) 0.0037(14) C15 0.0622(17) 0.0658(17) 0.0578(17) 0.0100(14) 0.0074(14) -0.0037(14) C16 0.0602(16) 0.0472(14) 0.0479(14) 0.0077(12) -0.0023(12) -0.0021(12) C17 0.0634(18) 0.081(2) 0.0643(18) -0.0160(16) -0.0044(15) -0.0090(16) C18 0.101(3) 0.108(3) 0.0523(18) -0.0012(17) 0.0165(18) -0.004(2) C19 0.0614(17) 0.0730(18) 0.0633(18) 0.0030(15) -0.0035(14) -0.0141(15) C21 0.0491(14) 0.0472(13) 0.0417(13) -0.0009(11) 0.0077(11) 0.0020(11) C22 0.0502(15) 0.0509(14) 0.0514(15) -0.0019(12) 0.0060(12) -0.0017(12) C23 0.0615(18) 0.0552(16) 0.072(2) 0.0048(14) 0.0125(14) -0.0034(13) C24 0.0701(19) 0.0659(17) 0.0573(17) 0.0102(14) 0.0168(14) 0.0105(15) C25 0.0725(19) 0.0766(19) 0.0398(14) 0.0046(14) 0.0096(13) 0.0203(16) C26 0.0533(15) 0.0646(16) 0.0396(13) -0.0060(12) 0.0068(11) 0.0098(13) C27 0.0706(19) 0.0676(18) 0.0654(19) -0.0011(15) -0.0073(15) -0.0188(15) C28 0.118(3) 0.089(2) 0.087(2) 0.032(2) 0.020(2) 0.002(2) C29 0.0693(19) 0.081(2) 0.0498(16) -0.0161(14) -0.0085(14) 0.0071(16) C31 0.0517(15) 0.0495(14) 0.0422(14) 0.0015(11) 0.0078(11) 0.0128(12) C32 0.0750(18) 0.0500(15) 0.0476(15) 0.0007(12) -0.0013(13) 0.0033(14) C33 0.096(2) 0.0510(16) 0.0612(18) 0.0116(14) 0.0072(17) 0.0039(15) C34 0.081(2) 0.0710(19) 0.0504(16) 0.0171(15) 0.0100(15) 0.0222(17) C35 0.0536(17) 0.091(2) 0.0525(16) 0.0012(16) -0.0007(13) 0.0173(16) C36 0.0511(15) 0.0606(15) 0.0581(16) 0.0022(13) 0.0060(13) 0.0055(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 P1 C2 1.725(2) . ? P1 C31 1.842(2) . ? N1 C3 1.390(3) . ? N1 C2 1.423(3) . ? N1 C11 1.460(3) . ? O1 C3 1.218(3) . ? N2 C5 1.394(3) . ? N2 C2 1.414(3) . ? N2 C21 1.460(3) . ? O2 C5 1.219(3) . ? C3 C4 1.513(4) . ? C4 C5 1.514(4) . ? C4 C6 1.533(4) . ? C4 C7 1.553(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C11 C12 1.400(3) . ? C11 C16 1.400(4) . ? C12 C13 1.385(4) . ? C12 C17 1.503(4) . ? C13 C14 1.385(4) . ? C13 H13A 0.9300 . ? C14 C15 1.387(4) . ? C14 C18 1.524(4) . ? C15 C16 1.394(4) . ? C15 H15A 0.9300 . ? C16 C19 1.508(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C22 1.398(3) . ? C21 C26 1.401(3) . ? C22 C23 1.401(4) . ? C22 C27 1.501(4) . ? C23 C24 1.383(4) . ? C23 H23A 0.9300 . ? C24 C25 1.379(4) . ? C24 C28 1.516(4) . ? C25 C26 1.398(4) . ? C25 H25A 0.9300 . ? C26 C29 1.506(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C36 1.389(4) . ? C31 C32 1.395(4) . ? C32 C33 1.387(4) . ? C32 H32A 0.9300 . ? C33 C34 1.365(4) . ? C33 H33A 0.9300 . ? C34 C35 1.376(4) . ? C34 H34A 0.9300 . ? C35 C36 1.395(4) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C31 108.36(11) . . ? C3 N1 C2 124.8(2) . . ? C3 N1 C11 116.16(19) . . ? C2 N1 C11 118.59(18) . . ? C5 N2 C2 122.9(2) . . ? C5 N2 C21 114.98(19) . . ? C2 N2 C21 121.99(18) . . ? N2 C2 N1 114.05(19) . . ? N2 C2 P1 131.09(17) . . ? N1 C2 P1 114.75(16) . . ? O1 C3 N1 120.9(2) . . ? O1 C3 C4 122.6(2) . . ? N1 C3 C4 116.4(2) . . ? C3 C4 C5 111.27(19) . . ? C3 C4 C6 110.3(2) . . ? C5 C4 C6 111.0(2) . . ? C3 C4 C7 107.2(2) . . ? C5 C4 C7 106.7(2) . . ? C6 C4 C7 110.1(2) . . ? O2 C5 N2 120.5(2) . . ? O2 C5 C4 121.7(2) . . ? N2 C5 C4 117.7(2) . . ? 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 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C16 122.3(2) . . ? C12 C11 N1 119.0(2) . . ? C16 C11 N1 118.7(2) . . ? C13 C12 C11 117.3(2) . . ? C13 C12 C17 120.5(2) . . ? C11 C12 C17 122.2(2) . . ? C14 C13 C12 123.0(3) . . ? C14 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C13 C14 C15 117.6(2) . . ? C13 C14 C18 121.0(3) . . ? C15 C14 C18 121.4(3) . . ? C14 C15 C16 122.7(3) . . ? C14 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C15 C16 C11 117.0(2) . . ? C15 C16 C19 121.2(2) . . ? C11 C16 C19 121.7(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 122.1(2) . . ? C22 C21 N2 119.4(2) . . ? C26 C21 N2 118.3(2) . . ? C21 C22 C23 117.4(2) . . ? C21 C22 C27 122.4(2) . . ? C23 C22 C27 120.2(2) . . ? C24 C23 C22 122.5(3) . . ? C24 C23 H23A 118.7 . . ? C22 C23 H23A 118.7 . . ? C25 C24 C23 117.9(3) . . ? C25 C24 C28 121.5(3) . . ? C23 C24 C28 120.6(3) . . ? C24 C25 C26 122.9(3) . . ? C24 C25 H25A 118.5 . . ? C26 C25 H25A 118.5 . . ? C25 C26 C21 117.1(3) . . ? C25 C26 C29 120.9(2) . . ? C21 C26 C29 121.9(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 C31 C32 118.4(2) . . ? C36 C31 P1 120.3(2) . . ? C32 C31 P1 120.23(19) . . ? C33 C32 C31 120.3(3) . . ? C33 C32 H32A 119.9 . . ? C31 C32 H32A 119.9 . . ? C34 C33 C32 120.8(3) . . ? C34 C33 H33A 119.6 . . ? C32 C33 H33A 119.6 . . ? C33 C34 C35 119.9(3) . . ? C33 C34 H34A 120.1 . . ? C35 C34 H34A 120.1 . . ? C34 C35 C36 120.1(3) . . ? C34 C35 H35A 119.9 . . ? C36 C35 H35A 119.9 . . ? C31 C36 C35 120.5(3) . . ? C31 C36 H36A 119.8 . . ? C35 C36 H36A 119.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.218 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 946638' ####################################################################### # # 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_2PPh _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5-DAC=PPh _chemical_melting_point ? _chemical_formula_moiety {(C9H11)2-C3N2O2-P(C6H5)} _chemical_formula_sum 'C27 H27 N2 O2 P' _chemical_formula_weight 442.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.1331(10) _cell_length_b 12.6193(16) _cell_length_c 23.637(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2426.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _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 17974 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4267 _reflns_number_gt 2681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0748P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(18) _refine_ls_number_reflns 4267 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1125 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1603 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.92773(16) 0.90385(11) 0.04727(5) 0.0610(4) Uani 1 1 d . . . N1 N 1.0926(4) 0.9620(3) 0.14061(13) 0.0444(8) Uani 1 1 d . . . O2 O 1.4398(4) 1.1094(3) 0.10997(13) 0.0744(10) Uani 1 1 d . . . C1 C 1.0857(5) 0.9660(3) 0.08044(15) 0.0426(10) Uani 1 1 d . . . N2 N 1.2229(4) 1.0258(3) 0.06450(12) 0.0421(8) Uani 1 1 d . . . O1 O 1.2664(4) 1.0225(3) 0.21122(11) 0.0685(9) Uani 1 1 d . . . C21 C 1.2698(5) 1.0505(3) 0.00681(15) 0.0407(10) Uani 1 1 d . . . C22 C 1.3861(5) 0.9857(3) -0.01902(18) 0.0488(11) Uani 1 1 d . . . C26 C 1.2009(5) 1.1371(3) -0.02027(17) 0.0457(10) Uani 1 1 d . . . C11 C 0.9639(5) 0.9160(4) 0.17407(15) 0.0417(10) Uani 1 1 d . . . C25 C 1.2430(6) 1.1538(4) -0.07641(18) 0.0535(12) Uani 1 1 d . . . H25A H 1.1947 1.2098 -0.0958 0.064 Uiso 1 1 calc R . . C12 C 0.8270(5) 0.9781(4) 0.18724(16) 0.0498(11) Uani 1 1 d . . . C23 C 1.4251(5) 1.0080(4) -0.07512(18) 0.0564(12) Uani 1 1 d . . . H23A H 1.5023 0.9658 -0.0935 0.068 Uiso 1 1 calc R . . C16 C 0.9759(5) 0.8093(4) 0.19116(16) 0.0456(11) Uani 1 1 d . . . C24 C 1.3537(5) 1.0903(4) -0.10444(16) 0.0498(11) Uani 1 1 d . . . C29 C 1.0813(6) 1.2081(4) 0.0103(2) 0.0740(15) Uani 1 1 d . . . H29A H 1.0682 1.1838 0.0485 0.111 Uiso 1 1 calc R . . H29B H 0.9769 1.2063 -0.0086 0.111 Uiso 1 1 calc R . . H29C H 1.1226 1.2793 0.0105 0.111 Uiso 1 1 calc R . . C31 C 0.9582(6) 0.9239(4) -0.02863(18) 0.0542(12) Uani 1 1 d . . . C14 C 0.7074(6) 0.8271(4) 0.23572(17) 0.0557(12) Uani 1 1 d . . . C15 C 0.8448(6) 0.7680(4) 0.22202(17) 0.0526(12) Uani 1 1 d . . . H15A H 0.8500 0.6978 0.2339 0.063 Uiso 1 1 calc R . . C3 C 1.2272(5) 1.0136(3) 0.16183(18) 0.0483(11) Uani 1 1 d . . . C17 C 0.8173(6) 1.0928(4) 0.16901(19) 0.0696(14) Uani 1 1 d . . . H17A H 0.7157 1.1230 0.1819 0.104 Uiso 1 1 calc R . . H17B H 0.8224 1.0969 0.1285 0.104 Uiso 1 1 calc R . . H17C H 0.9078 1.1314 0.1850 0.104 Uiso 1 1 calc R . . C33 C 1.0726(9) 0.8666(6) -0.1179(2) 0.106(2) Uani 1 1 d . . . H33A H 1.1448 0.8235 -0.1380 0.127 Uiso 1 1 calc R . . C2 C 1.3151(6) 1.0573(4) 0.11041(18) 0.0525(11) Uani 1 1 d . . . C13 C 0.7000(6) 0.9321(4) 0.21739(17) 0.0570(12) Uani 1 1 d . . . H13A H 0.6072 0.9723 0.2257 0.068 Uiso 1 1 calc R . . C34 C 0.9737(10) 0.9390(8) -0.1456(3) 0.127(4) Uani 1 1 d . . . H34A H 0.9796 0.9449 -0.1847 0.152 Uiso 1 1 calc R . . C19 C 1.1231(6) 0.7443(4) 0.1762(2) 0.0648(13) Uani 1 1 d . . . H19A H 1.1103 0.6741 0.1912 0.097 Uiso 1 1 calc R . . H19B H 1.2198 0.7763 0.1921 0.097 Uiso 1 1 calc R . . H19C H 1.1338 0.7407 0.1358 0.097 Uiso 1 1 calc R . . C27 C 1.4615(6) 0.8922(4) 0.0111(2) 0.0700(14) Uani 1 1 d . . . H27A H 1.4218 0.8897 0.0494 0.105 Uiso 1 1 calc R . . H27B H 1.5790 0.8993 0.0113 0.105 Uiso 1 1 calc R . . H27C H 1.4316 0.8280 -0.0081 0.105 Uiso 1 1 calc R . . C18 C 0.5645(6) 0.7797(5) 0.2678(2) 0.0823(17) Uani 1 1 d . . . H18A H 0.5894 0.7076 0.2776 0.123 Uiso 1 1 calc R . . H18B H 0.4678 0.7815 0.2445 0.123 Uiso 1 1 calc R . . H18C H 0.5455 0.8198 0.3017 0.123 Uiso 1 1 calc R . . C35 C 0.8671(8) 1.0021(6) -0.1160(3) 0.112(3) Uani 1 1 d . . . H35A H 0.8008 1.0506 -0.1349 0.135 Uiso 1 1 calc R . . C28 C 1.3933(7) 1.1076(5) -0.16652(18) 0.0816(16) Uani 1 1 d . . . H28A H 1.3332 1.1678 -0.1803 0.122 Uiso 1 1 calc R . . H28B H 1.3626 1.0458 -0.1877 0.122 Uiso 1 1 calc R . . H28C H 1.5090 1.1201 -0.1708 0.122 Uiso 1 1 calc R . . C36 C 0.8590(6) 0.9928(5) -0.0573(2) 0.0812(16) Uani 1 1 d . . . H36A H 0.7847 1.0344 -0.0373 0.097 Uiso 1 1 calc R . . C32 C 1.0617(7) 0.8598(4) -0.0598(2) 0.0726(15) Uani 1 1 d . . . H32A H 1.1264 0.8103 -0.0410 0.087 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 0.0583(8) 0.0837(9) 0.0410(6) 0.0034(6) -0.0020(6) -0.0223(7) N1 0.044(2) 0.054(2) 0.0348(18) 0.0018(16) 0.0035(17) -0.0081(18) O2 0.061(2) 0.102(3) 0.0597(19) -0.0039(19) -0.0006(17) -0.042(2) C1 0.045(2) 0.051(3) 0.032(2) 0.0020(18) 0.003(2) -0.004(2) N2 0.0430(19) 0.050(2) 0.0337(19) 0.0009(16) 0.0039(16) -0.0041(18) O1 0.073(2) 0.095(2) 0.0372(17) -0.0047(16) -0.0063(17) -0.0198(19) C21 0.037(2) 0.047(2) 0.038(2) 0.0013(19) 0.0023(19) -0.004(2) C22 0.042(2) 0.055(3) 0.049(3) 0.002(2) 0.000(2) 0.003(2) C26 0.040(2) 0.047(3) 0.050(3) 0.003(2) 0.000(2) -0.007(2) C11 0.041(2) 0.055(3) 0.029(2) -0.003(2) -0.0029(18) 0.000(2) C25 0.057(3) 0.056(3) 0.048(3) 0.012(2) -0.005(2) -0.003(2) C12 0.053(3) 0.058(3) 0.038(2) -0.002(2) 0.003(2) -0.008(2) C23 0.046(3) 0.073(3) 0.051(3) -0.007(2) 0.014(2) 0.006(3) C16 0.043(3) 0.057(3) 0.038(2) 0.005(2) -0.006(2) -0.001(2) C24 0.054(3) 0.060(3) 0.036(2) 0.001(2) 0.001(2) -0.010(2) C29 0.082(4) 0.064(3) 0.076(3) 0.006(3) 0.013(3) 0.027(3) C31 0.053(3) 0.064(3) 0.046(2) 0.008(2) -0.003(2) -0.022(3) C14 0.056(3) 0.067(3) 0.044(3) -0.003(2) 0.006(2) -0.010(3) C15 0.058(3) 0.056(3) 0.044(3) 0.005(2) -0.005(2) -0.008(3) C3 0.049(3) 0.054(3) 0.042(2) 0.000(2) -0.005(2) -0.005(2) C17 0.080(4) 0.060(3) 0.069(3) -0.003(3) 0.008(3) 0.007(3) C33 0.122(6) 0.145(6) 0.050(4) -0.025(4) 0.011(4) -0.052(5) C2 0.050(3) 0.067(3) 0.041(2) -0.001(2) 0.001(2) -0.005(3) C13 0.051(3) 0.077(4) 0.044(3) -0.006(2) 0.009(2) 0.005(3) C34 0.127(7) 0.208(10) 0.046(4) 0.010(5) -0.006(4) -0.091(7) C19 0.063(3) 0.062(3) 0.069(3) -0.002(2) -0.006(3) 0.008(3) C27 0.074(3) 0.064(3) 0.072(3) 0.007(3) 0.010(3) 0.011(3) C18 0.070(3) 0.109(4) 0.069(3) 0.002(3) 0.021(3) -0.028(3) C35 0.096(5) 0.167(7) 0.074(5) 0.057(5) -0.037(4) -0.045(5) C28 0.101(4) 0.097(4) 0.047(3) 0.011(3) 0.014(3) -0.005(4) C36 0.073(3) 0.100(4) 0.070(4) 0.022(3) -0.012(3) -0.014(3) C32 0.081(4) 0.079(4) 0.058(3) -0.001(3) 0.010(3) -0.015(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 P1 C1 1.697(4) . ? P1 C31 1.829(4) . ? N1 C3 1.369(5) . ? N1 C1 1.424(4) . ? N1 C11 1.434(5) . ? O2 C2 1.209(5) . ? C1 N2 1.399(5) . ? N2 C2 1.378(5) . ? N2 C21 1.450(5) . ? O1 C3 1.216(4) . ? C21 C26 1.384(5) . ? C21 C22 1.392(5) . ? C22 C23 1.392(6) . ? C22 C27 1.509(6) . ? C26 C25 1.387(5) . ? C26 C29 1.507(6) . ? C11 C12 1.398(6) . ? C11 C16 1.409(6) . ? C25 C24 1.375(6) . ? C25 H25A 0.9300 . ? C12 C13 1.382(6) . ? C12 C17 1.512(6) . ? C23 C24 1.377(6) . ? C23 H23A 0.9300 . ? C16 C15 1.393(6) . ? C16 C19 1.493(6) . ? C24 C28 1.518(6) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C36 1.367(6) . ? C31 C32 1.380(6) . ? C14 C15 1.382(6) . ? C14 C13 1.396(6) . ? C14 C18 1.512(6) . ? C15 H15A 0.9300 . ? C3 C2 1.514(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C33 C32 1.379(7) . ? C33 C34 1.382(10) . ? C33 H33A 0.9300 . ? C13 H13A 0.9300 . ? C34 C35 1.369(10) . ? C34 H34A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C35 C36 1.394(8) . ? C35 H35A 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C36 H36A 0.9300 . ? C32 H32A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C31 106.67(19) . . ? C3 N1 C1 112.4(3) . . ? C3 N1 C11 125.0(3) . . ? C1 N1 C11 122.4(3) . . ? N2 C1 N1 104.9(3) . . ? N2 C1 P1 136.8(3) . . ? N1 C1 P1 118.4(3) . . ? C2 N2 C1 112.2(3) . . ? C2 N2 C21 122.4(3) . . ? C1 N2 C21 125.4(3) . . ? C26 C21 C22 122.4(4) . . ? C26 C21 N2 119.9(3) . . ? C22 C21 N2 117.7(4) . . ? C21 C22 C23 117.0(4) . . ? C21 C22 C27 121.9(4) . . ? C23 C22 C27 121.0(4) . . ? C21 C26 C25 117.5(4) . . ? C21 C26 C29 120.6(4) . . ? C25 C26 C29 121.9(4) . . ? C12 C11 C16 121.8(4) . . ? C12 C11 N1 118.5(4) . . ? C16 C11 N1 119.6(4) . . ? C24 C25 C26 122.3(4) . . ? C24 C25 H25A 118.8 . . ? C26 C25 H25A 118.8 . . ? C13 C12 C11 118.3(4) . . ? C13 C12 C17 120.7(4) . . ? C11 C12 C17 121.0(4) . . ? C24 C23 C22 122.4(4) . . ? C24 C23 H23A 118.8 . . ? C22 C23 H23A 118.8 . . ? C15 C16 C11 117.1(4) . . ? C15 C16 C19 122.1(4) . . ? C11 C16 C19 120.8(4) . . ? C25 C24 C23 118.2(4) . . ? C25 C24 C28 121.4(4) . . ? C23 C24 C28 120.3(4) . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 C31 C32 117.9(5) . . ? C36 C31 P1 119.7(4) . . ? C32 C31 P1 121.7(4) . . ? C15 C14 C13 118.3(4) . . ? C15 C14 C18 121.7(4) . . ? C13 C14 C18 119.9(5) . . ? C14 C15 C16 122.6(4) . . ? C14 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? O1 C3 N1 127.3(4) . . ? O1 C3 C2 127.8(4) . . ? N1 C3 C2 104.9(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C32 C33 C34 118.3(7) . . ? C32 C33 H33A 120.8 . . ? C34 C33 H33A 120.8 . . ? O2 C2 N2 127.4(4) . . ? O2 C2 C3 127.0(4) . . ? N2 C2 C3 105.7(4) . . ? C12 C13 C14 121.8(4) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C35 C34 C33 120.8(6) . . ? C35 C34 H34A 119.6 . . ? C33 C34 H34A 119.6 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C34 C35 C36 119.3(7) . . ? C34 C35 H35A 120.4 . . ? C36 C35 H35A 120.4 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C36 C35 121.3(6) . . ? C31 C36 H36A 119.3 . . ? C35 C36 H36A 119.3 . . ? C33 C32 C31 122.3(6) . . ? C33 C32 H32A 118.8 . . ? C31 C32 H32A 118.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.232 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 946639' ####################################################################### # # 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_1ClOTf _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'DAC-Cl Triflate' _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O2 Cl - S O3 C F3' _chemical_formula_sum 'C25 H28 Cl F3 N2 O5 S' _chemical_formula_weight 561.00 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' F F 0.0171 0.0103 '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' 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 P2(1)/c 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 8.7462(8) _cell_length_b 16.7795(16) _cell_length_c 18.8733(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.361(7) _cell_angle_gamma 90.00 _cell_volume 2752.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.479 _exptl_crystal_size_mid 0.354 _exptl_crystal_size_min 0.322 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _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 13546 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4821 _reflns_number_gt 3075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXS-97 (Sheldrick, 1990)' _computing_cell_refinement 'SHELXS-97 (Sheldrick, 1990)' _computing_data_reduction 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0795P)^2^+1.0507P] 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 4821 _refine_ls_number_parameters 380 _refine_ls_number_restraints 279 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.066 _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 Cl1 Cl 0.02241(11) 0.09450(7) 0.27178(5) 0.0761(4) Uani 1 1 d U . . N1 N 0.2062(3) 0.18548(16) 0.20916(14) 0.0489(7) Uani 1 1 d U . . N2 N 0.2944(3) 0.14108(15) 0.32443(13) 0.0458(6) Uani 1 1 d U . . O2 O 0.5240(3) 0.18302(17) 0.37789(15) 0.0812(8) Uani 1 1 d U . . C6 C 0.2665(4) 0.09840(19) 0.38992(17) 0.0508(8) Uani 1 1 d U . . C7 C 0.4419(4) 0.18020(19) 0.32350(19) 0.0535(8) Uani 1 1 d U . . O1 O 0.3515(3) 0.26989(16) 0.15009(14) 0.0734(8) Uani 1 1 d U . . C9 C 0.3485(4) 0.2275(2) 0.20046(18) 0.0522(8) Uani 1 1 d U . . C10 C 0.1886(4) 0.14513(19) 0.26846(18) 0.0504(8) Uani 1 1 d U . . C11 C 0.0850(4) 0.1862(2) 0.14880(19) 0.0593(9) Uani 1 1 d U . . C12 C 0.4847(4) 0.2052(2) 0.25183(19) 0.0550(9) Uani 1 1 d U . . C13 C 0.3146(4) 0.0196(2) 0.39715(19) 0.0588(9) Uani 1 1 d U . . C14 C 0.2910(5) -0.0184(2) 0.4606(2) 0.0716(11) Uani 1 1 d U . . H14A H 0.3214 -0.0713 0.4668 0.086 Uiso 1 1 calc R . . C16 C 0.2248(5) 0.0188(3) 0.5144(2) 0.0727(11) Uani 1 1 d U . . C17 C 0.0851(5) 0.1236(2) 0.0999(2) 0.0705(11) Uani 1 1 d U . . C19 C 0.2027(5) 0.1387(2) 0.4430(2) 0.0708(11) Uani 1 1 d U . . C22 C 0.6046(5) 0.2724(3) 0.2597(2) 0.0854(13) Uani 1 1 d U . . H22A H 0.5603 0.3188 0.2791 0.128 Uiso 1 1 calc R . . H22B H 0.6359 0.2849 0.2138 0.128 Uiso 1 1 calc R . . H22C H 0.6924 0.2555 0.2911 0.128 Uiso 1 1 calc R . . C23 C -0.0199(5) 0.2476(3) 0.1429(2) 0.0747(12) Uani 1 1 d U . . C24 C -0.0303(6) 0.1252(3) 0.0433(2) 0.0970(16) Uani 1 1 d U . . H24A H -0.0337 0.0847 0.0095 0.116 Uiso 1 1 calc R . . C25 C 0.3874(6) -0.0234(2) 0.3399(2) 0.0878(13) Uani 1 1 d U . . H25A H 0.4163 -0.0761 0.3560 0.132 Uiso 1 1 calc R . . H25B H 0.4772 0.0052 0.3293 0.132 Uiso 1 1 calc R . . H25C H 0.3154 -0.0267 0.2978 0.132 Uiso 1 1 calc R . . C26 C 0.1831(6) 0.0969(3) 0.5046(2) 0.0811(12) Uani 1 1 d U . . H26A H 0.1396 0.1232 0.5409 0.097 Uiso 1 1 calc R . . C27 C 0.5566(5) 0.1309(3) 0.2201(2) 0.0780(12) Uani 1 1 d U . . H27A H 0.4823 0.0886 0.2152 0.117 Uiso 1 1 calc R . . H27B H 0.6450 0.1142 0.2512 0.117 Uiso 1 1 calc R . . H27C H 0.5871 0.1439 0.1742 0.117 Uiso 1 1 calc R . . C29 C -0.1383(6) 0.1833(4) 0.0352(3) 0.1044(18) Uani 1 1 d U . . C30 C -0.0136(5) 0.3153(3) 0.1946(3) 0.1006(16) Uani 1 1 d U . . H30A H -0.0201 0.2950 0.2417 0.151 Uiso 1 1 calc R . . H30B H -0.0982 0.3508 0.1816 0.151 Uiso 1 1 calc R . . H30C H 0.0816 0.3436 0.1936 0.151 Uiso 1 1 calc R . . C31 C 0.2007(6) 0.0575(3) 0.1068(2) 0.0926(14) Uani 1 1 d U . . H31A H 0.1942 0.0296 0.1508 0.139 Uiso 1 1 calc R . . H31B H 0.3022 0.0793 0.1066 0.139 Uiso 1 1 calc R . . H31C H 0.1800 0.0213 0.0676 0.139 Uiso 1 1 calc R . . C32 C 0.1536(8) 0.2242(3) 0.4351(3) 0.125(2) Uani 1 1 d U . . H32A H 0.2390 0.2561 0.4241 0.187 Uiso 1 1 calc R . . H32B H 0.1193 0.2425 0.4789 0.187 Uiso 1 1 calc R . . H32C H 0.0711 0.2288 0.3973 0.187 Uiso 1 1 calc R . . C36 C 0.1973(6) -0.0251(3) 0.5827(2) 0.1075(17) Uani 1 1 d U . . H36A H 0.2306 0.0077 0.6232 0.161 Uiso 1 1 calc R . . H36B H 0.2543 -0.0740 0.5858 0.161 Uiso 1 1 calc R . . H36C H 0.0896 -0.0364 0.5822 0.161 Uiso 1 1 calc R . . C39 C -0.2636(8) 0.1825(4) -0.0280(4) 0.168(3) Uani 1 1 d U . . H39A H -0.2168 0.1823 -0.0717 0.252 Uiso 1 1 calc R . . H39B H -0.3268 0.2291 -0.0264 0.252 Uiso 1 1 calc R . . H39C H -0.3258 0.1357 -0.0257 0.252 Uiso 1 1 calc R . . C200 C -0.1335(6) 0.2442(3) 0.0844(3) 0.0981(16) Uani 1 1 d U . . H20A H -0.2076 0.2841 0.0786 0.118 Uiso 1 1 calc R . . S1 S -0.2203(3) -0.08684(11) 0.17903(12) 0.0738(6) Uani 0.52 1 d PDU A 1 O5 O -0.0782(6) -0.0838(4) 0.1478(4) 0.103(2) Uani 0.52 1 d PDU A 1 F1 F -0.4978(6) -0.0514(4) 0.1268(4) 0.118(2) Uani 0.52 1 d PDU A 1 C100 C -0.3616(9) -0.0505(4) 0.1041(4) 0.090(3) Uani 0.52 1 d PDU A 1 O4 O -0.2908(4) -0.16642(14) 0.19010(14) 0.0836(9) Uani 1 1 d DU . . O3 O -0.2404(4) -0.03252(17) 0.23486(16) 0.1017(11) Uani 1 1 d DU . . F3 F -0.3597(5) -0.0975(2) 0.04875(15) 0.1399(13) Uani 1 1 d DU . . F2 F -0.3197(5) 0.02163(17) 0.08661(18) 0.1442(13) Uani 1 1 d DU . . S1A S -0.3414(3) -0.08215(11) 0.18564(11) 0.0602(5) Uani 0.48 1 d PDU A 2 O4A O -0.5025(7) -0.0612(3) 0.1778(4) 0.083(2) Uani 0.48 1 d PDU A 2 F1A F -0.1373(10) -0.0663(4) 0.0964(5) 0.143(3) Uani 0.48 1 d PDU A 2 C101 C -0.2843(9) -0.0547(4) 0.1013(7) 0.087(4) Uani 0.48 1 d PDU A 2 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 Cl1 0.0533(6) 0.0999(8) 0.0745(7) 0.0326(5) 0.0042(4) -0.0205(5) N1 0.0460(16) 0.0535(16) 0.0478(16) 0.0083(13) 0.0078(12) -0.0052(13) N2 0.0493(16) 0.0474(15) 0.0411(15) 0.0001(12) 0.0067(12) -0.0033(12) O2 0.085(2) 0.0873(19) 0.0665(18) 0.0018(15) -0.0130(15) -0.0294(16) C6 0.062(2) 0.0460(18) 0.0434(18) 0.0047(14) 0.0030(15) -0.0041(16) C7 0.058(2) 0.0461(18) 0.056(2) -0.0057(16) 0.0021(17) -0.0067(16) O1 0.0756(18) 0.0772(17) 0.0691(17) 0.0228(14) 0.0152(13) -0.0172(14) C9 0.057(2) 0.0496(18) 0.052(2) -0.0004(16) 0.0169(16) -0.0070(16) C10 0.053(2) 0.0483(18) 0.052(2) 0.0051(15) 0.0125(16) -0.0038(15) C11 0.051(2) 0.067(2) 0.059(2) 0.0219(19) 0.0017(16) -0.0097(18) C12 0.050(2) 0.056(2) 0.061(2) -0.0040(16) 0.0106(16) -0.0091(16) C13 0.062(2) 0.051(2) 0.061(2) 0.0000(17) -0.0004(17) -0.0057(17) C14 0.079(3) 0.057(2) 0.076(3) 0.020(2) -0.007(2) -0.008(2) C16 0.079(3) 0.080(3) 0.056(2) 0.018(2) -0.006(2) -0.018(2) C17 0.079(3) 0.072(2) 0.056(2) 0.018(2) -0.0112(19) -0.018(2) C19 0.100(3) 0.057(2) 0.059(2) 0.0040(18) 0.026(2) 0.003(2) C22 0.073(3) 0.088(3) 0.096(3) 0.007(2) 0.012(2) -0.038(2) C23 0.058(2) 0.073(3) 0.092(3) 0.029(2) 0.007(2) -0.004(2) C24 0.116(4) 0.092(3) 0.074(3) 0.028(2) -0.031(3) -0.033(3) C25 0.107(3) 0.055(2) 0.105(3) -0.006(2) 0.031(3) 0.004(2) C26 0.109(3) 0.083(3) 0.055(2) 0.004(2) 0.023(2) -0.003(2) C27 0.067(3) 0.085(3) 0.086(3) -0.008(2) 0.021(2) 0.011(2) C29 0.102(4) 0.098(4) 0.102(4) 0.047(3) -0.036(3) -0.032(3) C30 0.071(3) 0.093(3) 0.139(4) 0.013(3) 0.022(3) 0.022(3) C31 0.116(4) 0.080(3) 0.077(3) -0.016(2) -0.012(3) -0.001(3) C32 0.205(6) 0.073(3) 0.111(4) 0.013(3) 0.085(4) 0.037(3) C36 0.123(4) 0.122(4) 0.073(3) 0.044(3) -0.005(3) -0.028(3) C39 0.156(5) 0.164(5) 0.158(5) 0.057(5) -0.096(5) -0.030(4) C200 0.073(3) 0.092(3) 0.125(4) 0.058(3) -0.010(3) -0.006(3) S1 0.0801(16) 0.0531(11) 0.0878(15) 0.0006(10) 0.0077(12) -0.0042(11) O5 0.077(4) 0.099(5) 0.139(6) 0.026(4) 0.035(4) -0.011(3) F1 0.093(4) 0.117(4) 0.144(5) 0.018(4) 0.004(4) 0.010(3) C100 0.099(8) 0.081(6) 0.088(6) -0.013(5) 0.003(6) 0.009(6) O4 0.120(2) 0.0498(14) 0.0835(19) 0.0053(13) 0.0237(16) 0.0003(15) O3 0.129(3) 0.0706(18) 0.099(2) -0.0216(17) -0.0172(19) 0.0101(18) F3 0.204(4) 0.134(3) 0.081(2) -0.0072(18) 0.011(2) 0.013(2) F2 0.207(4) 0.084(2) 0.148(3) 0.0466(19) 0.050(2) 0.007(2) S1A 0.0718(15) 0.0457(10) 0.0652(13) 0.0031(9) 0.0165(10) 0.0036(10) O4A 0.083(4) 0.063(3) 0.108(5) 0.016(4) 0.033(4) 0.014(3) F1A 0.149(6) 0.125(5) 0.173(7) 0.025(5) 0.093(5) 0.004(5) C101 0.095(8) 0.057(5) 0.112(8) 0.016(5) 0.020(6) 0.014(5) _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 Cl1 C10 1.691(3) . ? N1 C10 1.331(4) . ? N1 C9 1.456(4) . ? N1 C11 1.467(4) . ? N2 C10 1.326(4) . ? N2 C7 1.450(4) . ? N2 C6 1.472(4) . ? O2 C7 1.187(4) . ? C6 C19 1.377(5) . ? C6 C13 1.390(5) . ? C7 C12 1.503(5) . ? O1 C9 1.190(4) . ? C9 C12 1.498(5) . ? C11 C23 1.376(5) . ? C11 C17 1.398(5) . ? C12 C22 1.536(5) . ? C12 C27 1.545(5) . ? C13 C14 1.392(5) . ? C13 C25 1.498(5) . ? C14 C16 1.374(6) . ? C14 H14A 0.9300 . ? C16 C26 1.369(6) . ? C16 C36 1.526(5) . ? C17 C24 1.386(5) . ? C17 C31 1.497(6) . ? C19 C26 1.384(5) . ? C19 C32 1.500(6) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C200 1.402(6) . ? C23 C30 1.495(6) . ? C24 C29 1.355(7) . ? C24 H24A 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C29 C200 1.377(7) . ? C29 C39 1.528(7) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C200 H20A 0.9300 . ? S1 O3 1.419(3) . ? S1 O5 1.434(5) . ? S1 O4 1.495(3) . ? S1 C100 1.873(9) . ? F1 C100 1.310(7) . ? C100 F3 1.311(6) . ? C100 F2 1.317(7) . ? O4 S1A 1.481(3) . ? O3 S1A 1.468(3) . ? F3 C101 1.338(8) . ? F2 C101 1.340(7) . ? S1A O4A 1.444(6) . ? S1A C101 1.780(14) . ? F1A C101 1.314(8) . ? 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 C10 N1 C9 121.4(3) . . ? C10 N1 C11 121.1(3) . . ? C9 N1 C11 117.5(3) . . ? C10 N2 C7 120.7(3) . . ? C10 N2 C6 121.9(3) . . ? C7 N2 C6 117.4(3) . . ? C19 C6 C13 122.6(3) . . ? C19 C6 N2 119.3(3) . . ? C13 C6 N2 118.0(3) . . ? O2 C7 N2 117.5(3) . . ? O2 C7 C12 125.5(3) . . ? N2 C7 C12 116.6(3) . . ? O1 C9 N1 118.3(3) . . ? O1 C9 C12 125.5(3) . . ? N1 C9 C12 115.8(3) . . ? N2 C10 N1 124.1(3) . . ? N2 C10 Cl1 118.1(2) . . ? N1 C10 Cl1 117.8(3) . . ? C23 C11 C17 123.9(4) . . ? C23 C11 N1 119.1(4) . . ? C17 C11 N1 117.0(3) . . ? C9 C12 C7 113.1(3) . . ? C9 C12 C22 111.4(3) . . ? C7 C12 C22 110.7(3) . . ? C9 C12 C27 106.2(3) . . ? C7 C12 C27 106.1(3) . . ? C22 C12 C27 109.1(3) . . ? C6 C13 C14 116.6(3) . . ? C6 C13 C25 122.4(3) . . ? C14 C13 C25 121.0(3) . . ? C16 C14 C13 122.9(4) . . ? C16 C14 H14A 118.6 . . ? C13 C14 H14A 118.6 . . ? C26 C16 C14 117.6(4) . . ? C26 C16 C36 120.8(4) . . ? C14 C16 C36 121.6(4) . . ? C24 C17 C11 116.2(4) . . ? C24 C17 C31 120.6(4) . . ? C11 C17 C31 123.2(3) . . ? C6 C19 C26 117.4(4) . . ? C6 C19 C32 122.2(3) . . ? C26 C19 C32 120.4(4) . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C11 C23 C200 116.2(4) . . ? C11 C23 C30 122.7(4) . . ? C200 C23 C30 121.1(4) . . ? C29 C24 C17 122.7(5) . . ? C29 C24 H24A 118.7 . . ? C17 C24 H24A 118.7 . . ? C13 C25 H25A 109.5 . . ? C13 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C13 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C16 C26 C19 122.9(4) . . ? C16 C26 H26A 118.6 . . ? C19 C26 H26A 118.6 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C29 C200 119.3(4) . . ? C24 C29 C39 120.8(6) . . ? C200 C29 C39 119.9(6) . . ? C23 C30 H30A 109.5 . . ? C23 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C23 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C17 C31 H31A 109.5 . . ? C17 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C17 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C19 C32 H32A 109.5 . . ? C19 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C19 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C16 C36 H36A 109.5 . . ? C16 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C16 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C29 C39 H39A 109.5 . . ? C29 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C29 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C29 C200 C23 121.8(5) . . ? C29 C200 H20A 119.1 . . ? C23 C200 H20A 119.1 . . ? O3 S1 O5 117.8(3) . . ? O3 S1 O4 112.5(2) . . ? O5 S1 O4 118.6(3) . . ? O3 S1 C100 103.0(2) . . ? O5 S1 C100 102.0(3) . . ? O4 S1 C100 98.6(2) . . ? F1 C100 F3 110.2(6) . . ? F1 C100 F2 112.4(6) . . ? F3 C100 F2 108.9(6) . . ? F1 C100 S1 107.3(5) . . ? F3 C100 S1 109.9(5) . . ? F2 C100 S1 108.1(5) . . ? S1A O4 S1 42.66(12) . . ? S1 O3 S1A 44.02(13) . . ? C100 F3 C101 30.0(5) . . ? C100 F2 C101 30.0(5) . . ? O4A S1A O3 116.0(3) . . ? O4A S1A O4 121.4(3) . . ? O3 S1A O4 110.5(2) . . ? O4A S1A C101 102.3(3) . . ? O3 S1A C101 102.1(3) . . ? O4 S1A C101 100.7(2) . . ? F1A C101 F3 105.9(8) . . ? F1A C101 F2 109.4(8) . . ? F3 C101 F2 106.0(7) . . ? F1A C101 S1A 113.5(7) . . ? F3 C101 S1A 111.1(6) . . ? F2 C101 S1A 110.6(7) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.288 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 946640'