# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_OPCp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H29 F N3 O4 P, 2(C3 H6 O)' _chemical_formula_sum 'C36 H41 F N3 O6 P' _chemical_formula_weight 661.69 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' 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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.650(2) _cell_length_b 12.440(2) _cell_length_c 16.140(3) _cell_angle_alpha 105.39(2) _cell_angle_beta 90.16(2) _cell_angle_gamma 94.95(2) _cell_volume 1667.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3521 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 24.5 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _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 ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17054 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5882 _reflns_number_gt 4781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1378P)^2^+4.9359P] 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 5882 _refine_ls_number_parameters 444 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0858 _refine_ls_wR_factor_ref 0.2435 _refine_ls_wR_factor_gt 0.2339 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.09149(10) 0.41056(8) 0.31761(6) 0.0157(3) Uani 1 1 d . . . O4 O 0.1855(3) 0.4884(2) 0.38968(16) 0.0207(6) Uani 1 1 d . . . C1 C 0.1569(4) 0.4096(3) 0.2103(2) 0.0169(7) Uani 1 1 d . . . H1A H 0.2635 0.3904 0.2060 0.020 Uiso 1 1 calc R . . H1B H 0.0949 0.3505 0.1691 0.020 Uiso 1 1 calc R . . N1 N 0.1498(3) 0.5135(3) 0.18513(19) 0.0174(7) Uani 1 1 d . . . C2 C 0.2654(5) 0.6003(3) 0.2349(2) 0.0213(8) Uani 1 1 d . . . H2A H 0.3664 0.5711 0.2300 0.026 Uiso 1 1 calc R . . H2B H 0.2388 0.6185 0.2950 0.026 Uiso 1 1 calc R . . C3 C 0.2746(5) 0.7056(3) 0.2045(3) 0.0268(9) Uani 1 1 d . . . H3A H 0.1764 0.7387 0.2133 0.032 Uiso 1 1 calc R . . H3B H 0.3550 0.7595 0.2370 0.032 Uiso 1 1 calc R . . N4 N 0.3099(4) 0.6767(3) 0.1132(2) 0.0238(8) Uani 1 1 d . . . C5 C 0.1878(5) 0.5961(3) 0.0632(2) 0.0226(8) Uani 1 1 d . . . H5A H 0.2104 0.5792 0.0025 0.027 Uiso 1 1 calc R . . H5B H 0.0885 0.6277 0.0715 0.027 Uiso 1 1 calc R . . C6 C 0.1808(4) 0.4905(3) 0.0929(2) 0.0199(8) Uani 1 1 d . . . H6A H 0.0997 0.4371 0.0605 0.024 Uiso 1 1 calc R . . H6B H 0.2787 0.4574 0.0817 0.024 Uiso 1 1 calc R . . C11 C 0.4015(4) 0.7507(3) 0.0804(2) 0.0193(8) Uani 1 1 d . . . C12 C 0.4771(5) 0.7156(3) 0.0014(2) 0.0198(8) Uani 1 1 d . . . F12 F 0.4484(3) 0.60601(18) -0.04501(14) 0.0260(5) Uani 1 1 d . . . C13 C 0.5822(4) 0.7814(3) -0.0286(2) 0.0194(8) Uani 1 1 d . . . H13 H 0.632(2) 0.7514(14) -0.085(3) 0.023 Uiso 1 1 calc R . . C14 C 0.6219(4) 0.8930(3) 0.0196(2) 0.0171(8) Uani 1 1 d . . . C15 C 0.5475(4) 0.9318(3) 0.0972(2) 0.0172(8) Uani 1 1 d . . . C16 C 0.4372(4) 0.8620(3) 0.1267(2) 0.0193(8) Uani 1 1 d . . . H16 H 0.383(3) 0.8925(14) 0.182(3) 0.023 Uiso 1 1 calc R . . C17 C 0.7361(4) 0.9641(3) -0.0118(2) 0.0182(8) Uani 1 1 d . . . O3 O 0.8017(3) 0.9302(2) -0.08227(17) 0.0227(6) Uani 1 1 d . . . C18 C 0.7657(4) 1.0765(3) 0.0424(2) 0.0177(8) Uani 1 1 d . . . C19 C 0.6855(4) 1.1100(3) 0.1162(2) 0.0178(8) Uani 1 1 d . . . H19 H 0.7040(10) 1.185(4) 0.1489(16) 0.021 Uiso 1 1 calc R . . N20 N 0.5819(4) 1.0428(3) 0.14549(19) 0.0177(7) Uani 1 1 d . . . C20 C 0.8774(4) 1.1593(3) 0.0177(2) 0.0194(8) Uani 1 1 d . . . O1 O 0.9048(3) 1.2548(2) 0.06187(17) 0.0234(6) Uani 1 1 d . . . O2 O 0.9439(3) 1.1231(2) -0.05717(18) 0.0247(6) Uani 1 1 d . . . H2 H 0.9100 1.0582 -0.0797 0.037 Uiso 1 1 calc R . . C21 C 0.4993(5) 1.0861(3) 0.2240(2) 0.0215(8) Uani 1 1 d . . . H21 H 0.3889 1.0944 0.2164 0.026 Uiso 1 1 calc R . . C22 C 0.5816(5) 1.1691(3) 0.2985(3) 0.0288(9) Uani 1 1 d . . . H22A H 0.5225 1.2263 0.3337 0.035 Uiso 1 1 calc R . . H22B H 0.6895 1.1930 0.2919 0.035 Uiso 1 1 calc R . . C23 C 0.5423(5) 1.0496(4) 0.3020(3) 0.0289(9) Uani 1 1 d . . . H23A H 0.6267 1.0020 0.2974 0.035 Uiso 1 1 calc R . . H23B H 0.4596 1.0353 0.3392 0.035 Uiso 1 1 calc R . . C31 C 0.0960(4) 0.2665(3) 0.3198(2) 0.0193(8) Uani 1 1 d . . . C32 C 0.1727(5) 0.2434(4) 0.3879(3) 0.0289(9) Uani 1 1 d . . . H32 H 0.222(3) 0.300(3) 0.430(2) 0.035 Uiso 1 1 calc R . . C33 C 0.1735(6) 0.1334(4) 0.3924(3) 0.0384(11) Uani 1 1 d . . . H33 H 0.228(3) 0.1174(10) 0.439(3) 0.046 Uiso 1 1 calc R . . C34 C 0.0959(6) 0.0465(4) 0.3298(3) 0.0360(11) Uani 1 1 d . . . H34 H 0.0948(6) -0.035(4) 0.3342(4) 0.043 Uiso 1 1 calc R . . C35 C 0.0198(5) 0.0692(4) 0.2614(3) 0.0309(10) Uani 1 1 d . . . H35 H -0.031(3) 0.013(3) 0.220(2) 0.037 Uiso 1 1 calc R . . C36 C 0.0213(5) 0.1787(3) 0.2560(3) 0.0246(9) Uani 1 1 d . . . H36 H -0.030(3) 0.1943(9) 0.208(3) 0.030 Uiso 1 1 calc R . . C41 C -0.1113(4) 0.4353(3) 0.3223(2) 0.0177(8) Uani 1 1 d . . . C42 C -0.1734(4) 0.4678(3) 0.4036(2) 0.0212(8) Uani 1 1 d . . . H42 H -0.110(3) 0.4787(6) 0.452(3) 0.025 Uiso 1 1 calc R . . C43 C -0.3299(5) 0.4840(3) 0.4128(3) 0.0235(8) Uani 1 1 d . . . H43 H -0.373(2) 0.5064(12) 0.470(3) 0.028 Uiso 1 1 calc R . . C44 C -0.4256(5) 0.4686(4) 0.3405(3) 0.0259(9) Uani 1 1 d . . . H44 H -0.532(6) 0.4803(7) 0.3465(4) 0.031 Uiso 1 1 calc R . . C45 C -0.3637(5) 0.4362(3) 0.2595(3) 0.0258(9) Uani 1 1 d . . . H45 H -0.427(4) 0.4258(7) 0.212(3) 0.031 Uiso 1 1 calc R . . C46 C -0.2074(4) 0.4192(3) 0.2494(3) 0.0206(8) Uani 1 1 d . . . H46 H -0.167(2) 0.3969(12) 0.194(3) 0.025 Uiso 1 1 calc R . . C1S C 0.7793(9) 0.7471(5) 0.2381(6) 0.077(2) Uani 1 1 d . . . C2S C 0.8462(8) 0.7309(6) 0.3165(4) 0.0624(16) Uani 1 1 d . . . H2S1 H 0.9419 0.6970 0.3038 0.094 Uiso 1 1 calc R . . H2S2 H 0.7749 0.6830 0.3392 0.094 Uiso 1 1 calc R . . H2S3 H 0.8657 0.8020 0.3582 0.094 Uiso 1 1 calc R . . C3S C 0.7686(7) 0.6650(5) 0.1539(4) 0.0558(15) Uani 1 1 d . . . H3S1 H 0.6635 0.6325 0.1423 0.084 Uiso 1 1 calc R . . H3S2 H 0.8354 0.6072 0.1539 0.084 Uiso 1 1 calc R . . H3S3 H 0.8000 0.7014 0.1104 0.084 Uiso 1 1 calc R . . C4S C 0.3073(7) 0.8171(5) 0.4483(3) 0.0481(13) Uani 1 1 d . . . C5S C 0.4509(6) 0.7535(6) 0.4569(3) 0.0538(15) Uani 1 1 d . . . H5S1 H 0.5250 0.7626 0.4145 0.081 Uiso 1 1 calc R . . H5S2 H 0.4189 0.6754 0.4482 0.081 Uiso 1 1 calc R . . H5S3 H 0.4976 0.7832 0.5133 0.081 Uiso 1 1 calc R . . C6S C 0.1733(9) 0.7849(7) 0.4937(4) 0.075(2) Uani 1 1 d . . . H6S1 H 0.0863 0.8225 0.4826 0.112 Uiso 1 1 calc R . . H6S2 H 0.1970 0.8057 0.5543 0.112 Uiso 1 1 calc R . . H6S3 H 0.1484 0.7054 0.4741 0.112 Uiso 1 1 calc R . . O1S O 0.7804(9) 0.8475(6) 0.2315(6) 0.134(3) Uani 1 1 d . . . O2S O 0.2969(7) 0.8770(5) 0.4026(4) 0.0926(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0120(5) 0.0176(5) 0.0180(5) 0.0065(4) 0.0003(3) -0.0020(3) O4 0.0154(13) 0.0260(14) 0.0196(13) 0.0066(11) -0.0024(10) -0.0044(11) C1 0.0128(17) 0.0174(18) 0.0202(18) 0.0060(14) 0.0011(14) -0.0040(14) N1 0.0158(15) 0.0167(15) 0.0194(15) 0.0061(12) -0.0013(12) -0.0040(12) C2 0.025(2) 0.0198(19) 0.0178(18) 0.0061(15) -0.0012(15) -0.0087(16) C3 0.037(2) 0.020(2) 0.022(2) 0.0052(16) 0.0009(17) -0.0079(17) N4 0.0318(19) 0.0195(17) 0.0189(16) 0.0071(13) -0.0001(14) -0.0107(14) C5 0.026(2) 0.0213(19) 0.0202(19) 0.0077(16) -0.0061(16) -0.0082(16) C6 0.0190(19) 0.0196(19) 0.0195(18) 0.0059(15) -0.0038(15) -0.0087(15) C11 0.0191(19) 0.0172(18) 0.0226(19) 0.0084(15) -0.0029(15) -0.0025(15) C12 0.024(2) 0.0123(17) 0.0209(19) 0.0015(14) -0.0045(15) -0.0021(14) F12 0.0332(13) 0.0139(11) 0.0267(12) 0.0003(9) 0.0017(10) -0.0052(9) C13 0.0190(19) 0.0190(19) 0.0205(19) 0.0056(15) 0.0002(15) 0.0024(15) C14 0.0145(18) 0.0181(18) 0.0188(18) 0.0058(14) -0.0017(14) -0.0005(14) C15 0.0177(18) 0.0149(17) 0.0191(18) 0.0056(14) -0.0025(14) -0.0016(14) C16 0.0204(19) 0.0195(19) 0.0186(18) 0.0072(15) 0.0007(15) -0.0021(15) C17 0.0157(18) 0.0196(19) 0.0202(19) 0.0077(15) -0.0005(15) -0.0004(14) O3 0.0228(14) 0.0198(14) 0.0241(14) 0.0043(11) 0.0062(11) -0.0009(11) C18 0.0167(18) 0.0176(18) 0.0193(18) 0.0067(15) -0.0014(14) -0.0007(14) C19 0.0165(18) 0.0157(18) 0.0207(18) 0.0050(15) -0.0017(15) -0.0015(14) N20 0.0157(15) 0.0183(15) 0.0174(15) 0.0030(12) 0.0006(12) -0.0028(12) C20 0.0142(18) 0.023(2) 0.0224(19) 0.0091(16) -0.0029(15) -0.0015(15) O1 0.0229(14) 0.0202(14) 0.0250(14) 0.0055(11) -0.0025(11) -0.0069(11) O2 0.0218(14) 0.0244(15) 0.0266(15) 0.0068(12) 0.0050(12) -0.0052(11) C21 0.023(2) 0.0180(18) 0.0207(19) 0.0028(15) 0.0044(15) -0.0049(15) C22 0.034(2) 0.025(2) 0.021(2) -0.0002(17) 0.0054(17) -0.0062(18) C23 0.035(2) 0.029(2) 0.022(2) 0.0081(17) 0.0023(17) -0.0049(18) C31 0.0162(18) 0.0210(19) 0.0235(19) 0.0103(15) 0.0058(15) 0.0022(14) C32 0.029(2) 0.030(2) 0.031(2) 0.0139(18) -0.0013(18) 0.0003(18) C33 0.045(3) 0.039(3) 0.040(3) 0.024(2) 0.001(2) 0.010(2) C34 0.044(3) 0.025(2) 0.047(3) 0.021(2) 0.009(2) 0.007(2) C35 0.035(2) 0.022(2) 0.034(2) 0.0060(18) 0.0085(19) -0.0010(18) C36 0.022(2) 0.024(2) 0.030(2) 0.0115(17) 0.0034(17) -0.0019(16) C41 0.0140(17) 0.0150(17) 0.0247(19) 0.0071(14) 0.0010(14) -0.0017(14) C42 0.0189(19) 0.024(2) 0.0207(19) 0.0063(16) -0.0031(16) -0.0002(15) C43 0.020(2) 0.028(2) 0.021(2) 0.0051(16) 0.0040(16) 0.0016(16) C44 0.015(2) 0.033(2) 0.029(2) 0.0065(18) 0.0016(16) 0.0028(16) C45 0.019(2) 0.030(2) 0.026(2) 0.0042(17) -0.0055(17) 0.0011(16) C46 0.0190(19) 0.0214(19) 0.0202(19) 0.0039(15) 0.0005(15) 0.0004(15) C1S 0.070(4) 0.039(3) 0.117(6) 0.006(4) -0.034(4) 0.025(3) C2S 0.062(4) 0.062(4) 0.071(4) 0.030(3) 0.011(3) 0.008(3) C3S 0.059(4) 0.065(4) 0.053(3) 0.029(3) 0.011(3) 0.020(3) C4S 0.060(4) 0.046(3) 0.040(3) 0.015(2) 0.002(3) 0.005(3) C5S 0.038(3) 0.078(4) 0.033(3) -0.009(3) -0.002(2) 0.010(3) C6S 0.068(4) 0.101(6) 0.053(4) 0.022(4) -0.003(3) -0.012(4) O1S 0.136(6) 0.079(4) 0.189(8) 0.044(5) -0.024(6) 0.001(4) O2S 0.121(5) 0.081(4) 0.094(4) 0.051(3) -0.004(3) 0.024(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 O4 1.487(3) . ? P1 C41 1.805(4) . ? P1 C31 1.806(4) . ? P1 C1 1.821(4) . ? C1 N1 1.461(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 C2 1.469(5) . ? N1 C6 1.470(5) . ? C2 C3 1.512(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.461(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N4 C11 1.376(5) . ? N4 C5 1.468(5) . ? C5 C6 1.509(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C11 C16 1.395(5) . ? C11 C12 1.414(5) . ? C12 C13 1.347(5) . ? C12 F12 1.371(4) . ? C13 C14 1.411(5) . ? C13 H13 0.9950 . ? C14 C15 1.398(5) . ? C14 C17 1.452(5) . ? C15 N20 1.399(5) . ? C15 C16 1.403(5) . ? C16 H16 1.0018 . ? C17 O3 1.258(5) . ? C17 C18 1.440(5) . ? C18 C19 1.365(5) . ? C18 C20 1.484(5) . ? C19 N20 1.345(5) . ? C19 H19 0.9465 . ? N20 C21 1.454(5) . ? C20 O1 1.215(5) . ? C20 O2 1.324(5) . ? O2 H2 0.8200 . ? C21 C22 1.493(5) . ? C21 C23 1.503(6) . ? C21 H21 0.9800 . ? C22 C23 1.511(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C31 C32 1.389(6) . ? C31 C36 1.397(6) . ? C32 C33 1.389(6) . ? C32 H32 0.9110 . ? C33 C34 1.390(7) . ? C33 H33 0.9623 . ? C34 C35 1.388(7) . ? C34 H34 1.0364 . ? C35 C36 1.386(6) . ? C35 H35 0.9049 . ? C36 H36 0.9693 . ? C41 C42 1.390(5) . ? C41 C46 1.399(5) . ? C42 C43 1.388(6) . ? C42 H42 0.9248 . ? C43 C44 1.391(6) . ? C43 H43 0.9805 . ? C44 C45 1.384(6) . ? C44 H44 0.9470 . ? C45 C46 1.390(6) . ? C45 H45 0.9143 . ? C46 H46 0.9456 . ? C1S O1S 1.280(9) . ? C1S C2S 1.459(10) . ? C1S C3S 1.465(10) . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? C3S H3S1 0.9600 . ? C3S H3S2 0.9600 . ? C3S H3S3 0.9600 . ? C4S O2S 1.187(7) . ? C4S C6S 1.456(9) . ? C4S C5S 1.554(8) . ? C5S H5S1 0.9600 . ? C5S H5S2 0.9600 . ? C5S H5S3 0.9600 . ? C6S H6S1 0.9600 . ? C6S H6S2 0.9600 . ? C6S H6S3 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 O4 P1 C41 112.42(17) . . ? O4 P1 C31 111.75(17) . . ? C41 P1 C31 105.22(17) . . ? O4 P1 C1 115.40(16) . . ? C41 P1 C1 107.92(17) . . ? C31 P1 C1 103.27(17) . . ? N1 C1 P1 116.4(3) . . ? N1 C1 H1A 108.2 . . ? P1 C1 H1A 108.2 . . ? N1 C1 H1B 108.2 . . ? P1 C1 H1B 108.2 . . ? H1A C1 H1B 107.3 . . ? C1 N1 C2 110.3(3) . . ? C1 N1 C6 108.1(3) . . ? C2 N1 C6 110.2(3) . . ? N1 C2 C3 112.2(3) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C2 108.8(3) . . ? N4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? N4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C11 N4 C3 120.1(3) . . ? C11 N4 C5 123.8(3) . . ? C3 N4 C5 110.4(3) . . ? N4 C5 C6 108.9(3) . . ? N4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N1 C6 C5 111.3(3) . . ? N1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N4 C11 C16 121.9(4) . . ? N4 C11 C12 121.7(3) . . ? C16 C11 C12 116.1(3) . . ? C13 C12 F12 117.9(3) . . ? C13 C12 C11 124.0(3) . . ? F12 C12 C11 117.9(3) . . ? C12 C13 C14 119.9(4) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 118.0(3) . . ? C15 C14 C17 121.8(3) . . ? C13 C14 C17 120.3(3) . . ? C14 C15 N20 119.3(3) . . ? C14 C15 C16 121.1(3) . . ? N20 C15 C16 119.6(3) . . ? C11 C16 C15 120.9(4) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? O3 C17 C18 122.8(3) . . ? O3 C17 C14 122.1(3) . . ? C18 C17 C14 115.2(3) . . ? C19 C18 C17 120.0(3) . . ? C19 C18 C20 118.8(3) . . ? C17 C18 C20 121.1(3) . . ? N20 C19 C18 124.3(3) . . ? N20 C19 H19 117.8 . . ? C18 C19 H19 117.8 . . ? C19 N20 C15 119.4(3) . . ? C19 N20 C21 120.6(3) . . ? C15 N20 C21 119.9(3) . . ? O1 C20 O2 121.7(3) . . ? O1 C20 C18 122.8(3) . . ? O2 C20 C18 115.5(3) . . ? C20 O2 H2 109.5 . . ? N20 C21 C22 119.9(3) . . ? N20 C21 C23 117.6(4) . . ? C22 C21 C23 60.6(3) . . ? N20 C21 H21 115.8 . . ? C22 C21 H21 115.8 . . ? C23 C21 H21 115.8 . . ? C21 C22 C23 60.0(3) . . ? C21 C22 H22A 117.8 . . ? C23 C22 H22A 117.8 . . ? C21 C22 H22B 117.8 . . ? C23 C22 H22B 117.8 . . ? H22A C22 H22B 114.9 . . ? C21 C23 C22 59.4(3) . . ? C21 C23 H23A 117.8 . . ? C22 C23 H23A 117.8 . . ? C21 C23 H23B 117.8 . . ? C22 C23 H23B 117.8 . . ? H23A C23 H23B 115.0 . . ? C32 C31 C36 119.6(4) . . ? C32 C31 P1 118.9(3) . . ? C36 C31 P1 121.6(3) . . ? C31 C32 C33 119.9(4) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C32 C33 C34 120.4(4) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 119.9(4) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C36 C35 C34 119.8(4) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C31 120.5(4) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? C42 C41 C46 119.6(3) . . ? C42 C41 P1 116.8(3) . . ? C46 C41 P1 123.5(3) . . ? C43 C42 C41 120.5(4) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C42 C43 C44 120.0(4) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C45 C44 C43 119.5(4) . . ? C45 C44 H44 120.3 . . ? C43 C44 H44 120.3 . . ? C44 C45 C46 121.1(4) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C45 C46 C41 119.3(4) . . ? C45 C46 H46 120.3 . . ? C41 C46 H46 120.3 . . ? O1S C1S C2S 117.7(7) . . ? O1S C1S C3S 111.9(8) . . ? C2S C1S C3S 125.7(5) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? C1S C3S H3S1 109.5 . . ? C1S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? C1S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? O2S C4S C6S 120.9(7) . . ? O2S C4S C5S 125.4(6) . . ? C6S C4S C5S 113.2(5) . . ? C4S C5S H5S1 109.5 . . ? C4S C5S H5S2 109.5 . . ? H5S1 C5S H5S2 109.5 . . ? C4S C5S H5S3 109.5 . . ? H5S1 C5S H5S3 109.5 . . ? H5S2 C5S H5S3 109.5 . . ? C4S C6S H6S1 109.5 . . ? C4S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C4S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 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 O4 P1 C1 N1 -64.2(3) . . . . ? C41 P1 C1 N1 62.5(3) . . . . ? C31 P1 C1 N1 173.5(3) . . . . ? P1 C1 N1 C2 69.2(3) . . . . ? P1 C1 N1 C6 -170.3(2) . . . . ? C1 N1 C2 C3 173.8(3) . . . . ? C6 N1 C2 C3 54.6(4) . . . . ? N1 C2 C3 N4 -57.1(4) . . . . ? C2 C3 N4 C11 -145.4(4) . . . . ? C2 C3 N4 C5 60.3(4) . . . . ? C11 N4 C5 C6 145.5(4) . . . . ? C3 N4 C5 C6 -61.4(4) . . . . ? C1 N1 C6 C5 -175.6(3) . . . . ? C2 N1 C6 C5 -55.1(4) . . . . ? N4 C5 C6 N1 58.5(4) . . . . ? C3 N4 C11 C16 -13.3(6) . . . . ? C5 N4 C11 C16 137.4(4) . . . . ? C3 N4 C11 C12 160.4(4) . . . . ? C5 N4 C11 C12 -48.9(6) . . . . ? N4 C11 C12 C13 -171.8(4) . . . . ? C16 C11 C12 C13 2.3(6) . . . . ? N4 C11 C12 F12 4.3(6) . . . . ? C16 C11 C12 F12 178.3(3) . . . . ? F12 C12 C13 C14 -176.5(3) . . . . ? C11 C12 C13 C14 -0.4(6) . . . . ? C12 C13 C14 C15 -0.9(5) . . . . ? C12 C13 C14 C17 179.4(3) . . . . ? C13 C14 C15 N20 -178.6(3) . . . . ? C17 C14 C15 N20 1.1(5) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C17 C14 C15 C16 179.9(3) . . . . ? N4 C11 C16 C15 171.2(3) . . . . ? C12 C11 C16 C15 -2.9(5) . . . . ? C14 C15 C16 C11 1.8(6) . . . . ? N20 C15 C16 C11 -179.4(3) . . . . ? C15 C14 C17 O3 -178.9(3) . . . . ? C13 C14 C17 O3 0.8(6) . . . . ? C15 C14 C17 C18 -0.3(5) . . . . ? C13 C14 C17 C18 179.4(3) . . . . ? O3 C17 C18 C19 176.9(3) . . . . ? C14 C17 C18 C19 -1.7(5) . . . . ? O3 C17 C18 C20 -0.2(6) . . . . ? C14 C17 C18 C20 -178.8(3) . . . . ? C17 C18 C19 N20 3.1(6) . . . . ? C20 C18 C19 N20 -179.7(3) . . . . ? C18 C19 N20 C15 -2.3(6) . . . . ? C18 C19 N20 C21 -178.8(4) . . . . ? C14 C15 N20 C19 0.1(5) . . . . ? C16 C15 N20 C19 -178.7(3) . . . . ? C14 C15 N20 C21 176.6(3) . . . . ? C16 C15 N20 C21 -2.2(5) . . . . ? C19 C18 C20 O1 2.7(6) . . . . ? C17 C18 C20 O1 179.8(3) . . . . ? C19 C18 C20 O2 -176.0(3) . . . . ? C17 C18 C20 O2 1.1(5) . . . . ? C19 N20 C21 C22 -38.5(5) . . . . ? C15 N20 C21 C22 145.1(4) . . . . ? C19 N20 C21 C23 -108.7(4) . . . . ? C15 N20 C21 C23 74.8(4) . . . . ? N20 C21 C22 C23 -106.8(4) . . . . ? N20 C21 C23 C22 110.6(4) . . . . ? O4 P1 C31 C32 4.4(4) . . . . ? C41 P1 C31 C32 -117.9(3) . . . . ? C1 P1 C31 C32 129.0(3) . . . . ? O4 P1 C31 C36 -177.1(3) . . . . ? C41 P1 C31 C36 60.6(3) . . . . ? C1 P1 C31 C36 -52.5(3) . . . . ? C36 C31 C32 C33 -0.5(6) . . . . ? P1 C31 C32 C33 178.0(3) . . . . ? C31 C32 C33 C34 -1.0(7) . . . . ? C32 C33 C34 C35 1.4(7) . . . . ? C33 C34 C35 C36 -0.2(7) . . . . ? C34 C35 C36 C31 -1.3(6) . . . . ? C32 C31 C36 C35 1.7(6) . . . . ? P1 C31 C36 C35 -176.8(3) . . . . ? O4 P1 C41 C42 -35.4(3) . . . . ? C31 P1 C41 C42 86.4(3) . . . . ? C1 P1 C41 C42 -163.8(3) . . . . ? O4 P1 C41 C46 147.2(3) . . . . ? C31 P1 C41 C46 -91.0(3) . . . . ? C1 P1 C41 C46 18.8(4) . . . . ? C46 C41 C42 C43 0.1(6) . . . . ? P1 C41 C42 C43 -177.4(3) . . . . ? C41 C42 C43 C44 -0.5(6) . . . . ? C42 C43 C44 C45 0.5(6) . . . . ? C43 C44 C45 C46 -0.3(6) . . . . ? C44 C45 C46 C41 -0.1(6) . . . . ? C42 C41 C46 C45 0.1(5) . . . . ? P1 C41 C46 C45 177.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 1.77 2.531(4) 154.2 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.208 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.109 # start Validation Reply Form _vrf_DIFMX01_OPCp ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 RESPONSE: there is a large maximum of electron density (2.21 eA-3) close to one of the highly disordered molecules of occluded acetone solvent (d(Q1-C1S) = 1.431A, d(Q1-O1S) = 1.803A) ; _vrf_PLAT097_OPCp ; PROBLEM: Large Reported Max. (Positive) Residual Density 2.21 eA-3 RESPONSE: this large maximum of electron density is close to one of the highly disordered molecules of acetone solvent ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 948747' ####################################################################### # # 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_SPCp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H29 F N3 O3 P S, 0.5(C H2 Cl2)' _chemical_formula_sum 'C30.50 H30 Cl F N3 O3 P S' _chemical_formula_weight 604.05 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.748(1) _cell_length_b 22.372(3) _cell_length_c 14.514(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.60(2) _cell_angle_gamma 90.00 _cell_volume 2831.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2459 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 24.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.310 _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 293(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 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19067 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4988 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4988 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.322 _refine_ls_restrained_S_all 1.322 _refine_ls_shift/su_max 0.022 _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 O3 O 0.3477(2) 0.00352(9) 0.59431(12) 0.0215(5) Uani 1 1 d . . . N20 N -0.0508(3) 0.09448(10) 0.51861(15) 0.0153(5) Uani 1 1 d . . . C18 C 0.1212(3) 0.05017(12) 0.63579(18) 0.0173(6) Uani 1 1 d . . . C19 C -0.0118(3) 0.07917(12) 0.60681(18) 0.0162(6) Uani 1 1 d . . . H19 H -0.0793 0.0889 0.6509 0.019 Uiso 1 1 calc R . . C21 C -0.1978(3) 0.12290(13) 0.49386(18) 0.0189(6) Uani 1 1 d . . . H21 H -0.2773 0.0971 0.4636 0.023 Uiso 1 1 calc R . . C17 C 0.2265(3) 0.03248(12) 0.57077(18) 0.0155(6) Uani 1 1 d . . . O1 O 0.0702(2) 0.05538(9) 0.79422(13) 0.0241(5) Uani 1 1 d . . . O2 O 0.2703(2) 0.00182(9) 0.75878(13) 0.0239(5) Uani 1 1 d . . . H2 H 0.3132 -0.0064 0.7122 0.036 Uiso 1 1 calc R . . C20 C 0.1506(3) 0.03627(13) 0.73627(19) 0.0187(6) Uani 1 1 d . . . C23 C -0.2533(4) 0.17049(14) 0.55472(19) 0.0246(7) Uani 1 1 d . . . H23A H -0.1880 0.1813 0.6094 0.029 Uiso 1 1 calc R . . H23B H -0.3624 0.1724 0.5619 0.029 Uiso 1 1 calc R . . C22 C -0.2000(4) 0.18673(13) 0.4626(2) 0.0244(7) Uani 1 1 d . . . H22A H -0.1025 0.2073 0.4615 0.029 Uiso 1 1 calc R . . H22B H -0.2770 0.1983 0.4141 0.029 Uiso 1 1 calc R . . P1 P -0.09472(8) 0.23406(3) -0.11735(4) 0.0157(2) Uani 1 1 d . . . S1 S -0.14172(9) 0.30490(3) -0.04549(5) 0.0202(2) Uani 1 1 d . . . F12 F 0.34232(19) 0.04081(7) 0.25169(10) 0.0236(4) Uani 1 1 d . . . N4 N 0.0747(3) 0.10222(11) 0.19880(15) 0.0201(6) Uani 1 1 d . . . C16 C 0.0070(3) 0.09461(12) 0.35772(18) 0.0173(6) Uani 1 1 d . . . H16 H -0.0862 0.1135 0.3423 0.021 Uiso 1 1 calc R . . C14 C 0.1849(3) 0.04880(12) 0.47514(18) 0.0157(6) Uani 1 1 d . . . N1 N 0.0031(3) 0.14711(10) 0.01534(15) 0.0173(5) Uani 1 1 d . . . C15 C 0.0472(3) 0.07989(12) 0.44967(17) 0.0145(6) Uani 1 1 d . . . C13 C 0.2811(3) 0.03472(12) 0.40558(18) 0.0173(6) Uani 1 1 d . . . H13 H 0.3724 0.0143 0.4203 0.021 Uiso 1 1 calc R . . C12 C 0.2411(3) 0.05088(12) 0.31660(18) 0.0184(6) Uani 1 1 d . . . C5 C -0.0401(4) 0.14869(14) 0.17977(19) 0.0244(7) Uani 1 1 d . . . H5A H -0.0443 0.1743 0.2334 0.029 Uiso 1 1 calc R . . H5B H -0.1403 0.1307 0.1665 0.029 Uiso 1 1 calc R . . C6 C 0.0021(4) 0.18518(13) 0.09754(18) 0.0205(6) Uani 1 1 d . . . H6A H -0.0714 0.2173 0.0859 0.025 Uiso 1 1 calc R . . H6B H 0.1027 0.2028 0.1110 0.025 Uiso 1 1 calc R . . C2 C 0.1159(4) 0.09886(13) 0.03396(18) 0.0198(7) Uani 1 1 d . . . H2A H 0.2176 0.1160 0.0444 0.024 Uiso 1 1 calc R . . H2B H 0.1152 0.0729 -0.0196 0.024 Uiso 1 1 calc R . . C11 C 0.1027(3) 0.08174(12) 0.28847(18) 0.0173(6) Uani 1 1 d . . . C31 C -0.2658(3) 0.19270(13) -0.15786(18) 0.0180(6) Uani 1 1 d . . . C41 C -0.0111(3) 0.25501(13) -0.22405(18) 0.0176(6) Uani 1 1 d . . . C1 C 0.0454(3) 0.18065(13) -0.06524(18) 0.0181(6) Uani 1 1 d . . . H1A H 0.0684 0.1521 -0.1125 0.022 Uiso 1 1 calc R . . H1B H 0.1392 0.2023 -0.0476 0.022 Uiso 1 1 calc R . . C3 C 0.0804(4) 0.06232(13) 0.11799(17) 0.0219(7) Uani 1 1 d . . . H3A H -0.0173 0.0422 0.1059 0.026 Uiso 1 1 calc R . . H3B H 0.1590 0.0322 0.1306 0.026 Uiso 1 1 calc R . . C46 C 0.0614(3) 0.21376(14) -0.27764(19) 0.0204(6) Uani 1 1 d . . . H46 H 0.0732 0.1744 -0.2579 0.024 Uiso 1 1 calc R . . C45 C 0.1161(4) 0.23153(15) -0.36053(19) 0.0254(7) Uani 1 1 d . . . H45 H 0.1672 0.2042 -0.3953 0.030 Uiso 1 1 calc R . . C43 C 0.0224(4) 0.33072(16) -0.3392(2) 0.0320(8) Uani 1 1 d . . . H43 H 0.0085 0.3697 -0.3603 0.038 Uiso 1 1 calc R . . C42 C -0.0300(4) 0.31405(14) -0.2551(2) 0.0268(7) Uani 1 1 d . . . H42 H -0.0775 0.3420 -0.2195 0.032 Uiso 1 1 calc R . . C36 C -0.4027(4) 0.22376(15) -0.1676(2) 0.0316(8) Uani 1 1 d . . . H36 H -0.4066 0.2630 -0.1466 0.038 Uiso 1 1 calc R . . C44 C 0.0952(4) 0.28951(16) -0.3918(2) 0.0273(7) Uani 1 1 d . . . H44 H 0.1300 0.3008 -0.4481 0.033 Uiso 1 1 calc R . . C32 C -0.2621(4) 0.13361(14) -0.1868(2) 0.0303(8) Uani 1 1 d . . . H32 H -0.1713 0.1119 -0.1793 0.036 Uiso 1 1 calc R . . C34 C -0.5276(4) 0.13908(17) -0.2393(3) 0.0430(9) Uani 1 1 d . . . H34 H -0.6146 0.1216 -0.2690 0.052 Uiso 1 1 calc R . . C35 C -0.5332(4) 0.19728(16) -0.2079(3) 0.0451(10) Uani 1 1 d . . . H35 H -0.6250 0.2185 -0.2140 0.054 Uiso 1 1 calc R . . C33 C -0.3944(4) 0.10714(16) -0.2268(3) 0.0438(10) Uani 1 1 d . . . H33 H -0.3926 0.0674 -0.2452 0.053 Uiso 1 1 calc R . . C50 C -0.0295(11) 0.4851(4) 0.4406(6) 0.056(2) Uiso 0.50 1 d P . . Cl1 Cl 0.1498(3) 0.45421(12) 0.50310(16) 0.0493(6) Uiso 0.50 1 d P . . Cl2 Cl -0.1034(5) 0.5307(2) 0.4944(3) 0.1096(15) Uiso 0.50 1 d P . . 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 O3 0.0196(11) 0.0235(11) 0.0207(10) 0.0023(8) -0.0033(8) 0.0051(9) N20 0.0154(13) 0.0127(12) 0.0173(11) -0.0004(9) -0.0011(9) 0.0017(10) C18 0.0192(16) 0.0138(14) 0.0183(13) -0.0004(11) -0.0025(11) -0.0015(12) C19 0.0183(16) 0.0149(14) 0.0152(13) -0.0001(11) 0.0002(11) -0.0037(12) C21 0.0138(15) 0.0200(16) 0.0222(14) -0.0006(12) -0.0033(11) 0.0020(12) C17 0.0139(15) 0.0120(14) 0.0202(14) 0.0000(11) -0.0003(11) -0.0009(12) O1 0.0325(13) 0.0218(11) 0.0177(10) 0.0008(8) 0.0001(9) 0.0027(10) O2 0.0270(12) 0.0260(12) 0.0180(10) 0.0023(9) -0.0029(8) 0.0070(10) C20 0.0206(16) 0.0157(15) 0.0194(14) -0.0009(11) -0.0017(12) -0.0023(13) C23 0.0203(17) 0.0287(17) 0.0240(15) -0.0036(13) -0.0026(12) 0.0080(14) C22 0.0260(18) 0.0204(16) 0.0260(15) 0.0038(12) -0.0025(13) 0.0054(13) P1 0.0155(4) 0.0165(4) 0.0149(4) 0.0020(3) 0.0007(3) 0.0007(3) S1 0.0228(4) 0.0185(4) 0.0194(4) -0.0007(3) 0.0012(3) 0.0032(3) F12 0.0253(10) 0.0256(10) 0.0205(8) 0.0029(7) 0.0069(7) 0.0069(8) N4 0.0284(15) 0.0175(13) 0.0145(11) 0.0032(9) 0.0019(10) 0.0078(11) C16 0.0162(15) 0.0145(14) 0.0209(14) 0.0006(11) -0.0014(11) 0.0012(12) C14 0.0181(15) 0.0115(14) 0.0170(13) -0.0008(11) -0.0014(11) -0.0015(12) N1 0.0210(13) 0.0147(12) 0.0159(11) 0.0025(9) 0.0005(9) 0.0020(10) C15 0.0155(15) 0.0108(14) 0.0170(13) -0.0016(11) 0.0013(11) -0.0022(11) C13 0.0166(15) 0.0136(14) 0.0211(14) 0.0028(11) -0.0023(11) 0.0021(12) C12 0.0198(16) 0.0153(15) 0.0208(14) -0.0030(11) 0.0066(12) 0.0009(12) C5 0.0311(19) 0.0230(16) 0.0192(14) 0.0025(12) 0.0023(12) 0.0109(14) C6 0.0258(17) 0.0184(15) 0.0172(13) 0.0027(11) 0.0017(12) 0.0066(13) C2 0.0253(17) 0.0172(15) 0.0167(13) 0.0003(11) 0.0000(12) 0.0057(13) C11 0.0234(17) 0.0120(14) 0.0160(13) 0.0007(11) -0.0021(11) -0.0012(12) C31 0.0159(15) 0.0193(15) 0.0192(14) 0.0027(11) 0.0041(11) -0.0002(12) C41 0.0144(15) 0.0220(16) 0.0161(13) 0.0006(11) -0.0018(11) -0.0018(12) C1 0.0177(15) 0.0230(16) 0.0138(13) 0.0017(12) 0.0020(11) 0.0020(12) C3 0.0319(19) 0.0163(15) 0.0172(14) 0.0017(11) -0.0001(12) 0.0034(13) C46 0.0184(16) 0.0218(16) 0.0204(14) -0.0014(12) -0.0011(11) -0.0010(13) C45 0.0231(17) 0.0338(18) 0.0196(14) -0.0033(13) 0.0041(12) -0.0045(14) C43 0.033(2) 0.0333(19) 0.0298(16) 0.0171(15) 0.0038(14) 0.0020(16) C42 0.0261(18) 0.0281(18) 0.0269(15) 0.0060(13) 0.0071(13) 0.0059(14) C36 0.0210(18) 0.0233(18) 0.049(2) -0.0045(15) -0.0058(14) 0.0022(14) C44 0.0232(17) 0.041(2) 0.0180(14) 0.0061(14) 0.0031(12) -0.0082(15) C32 0.0212(17) 0.0204(17) 0.049(2) 0.0001(15) 0.0025(14) 0.0010(14) C34 0.026(2) 0.032(2) 0.069(2) -0.0021(18) -0.0093(17) -0.0099(16) C35 0.0228(19) 0.027(2) 0.082(3) -0.0044(18) -0.0127(19) 0.0016(16) C33 0.035(2) 0.0186(18) 0.077(3) -0.0110(17) -0.0035(19) -0.0042(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C17 1.266(3) . ? N20 C19 1.342(3) . ? N20 C15 1.407(3) . ? N20 C21 1.454(3) . ? C18 C19 1.369(4) . ? C18 C17 1.426(4) . ? C18 C20 1.493(4) . ? C21 C23 1.489(4) . ? C21 C22 1.498(4) . ? C17 C14 1.453(4) . ? O1 C20 1.216(3) . ? O2 C20 1.320(3) . ? C23 C22 1.496(4) . ? P1 C31 1.817(3) . ? P1 C41 1.826(3) . ? P1 C1 1.831(3) . ? P1 S1 1.9590(10) . ? F12 C12 1.363(3) . ? N4 C11 1.383(3) . ? N4 C5 1.457(4) . ? N4 C3 1.478(3) . ? C16 C11 1.389(4) . ? C16 C15 1.392(4) . ? C14 C13 1.401(4) . ? C14 C15 1.414(4) . ? N1 C1 1.462(3) . ? N1 C6 1.466(3) . ? N1 C2 1.473(4) . ? C13 C12 1.360(4) . ? C12 C11 1.425(4) . ? C5 C6 1.516(4) . ? C2 C3 1.521(4) . ? C31 C36 1.382(4) . ? C31 C32 1.388(4) . ? C41 C46 1.392(4) . ? C41 C42 1.401(4) . ? C46 C45 1.388(4) . ? C45 C44 1.382(5) . ? C43 C44 1.384(5) . ? C43 C42 1.389(4) . ? C36 C35 1.375(5) . ? C32 C33 1.386(5) . ? C34 C33 1.366(5) . ? C34 C35 1.382(5) . ? C50 Cl2 1.466(9) . ? C50 Cl1 1.937(10) 3_566 ? C50 Cl2 1.480(10) 3_566 ? C50 Cl1 1.879(9) . ? 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 C19 N20 C15 119.8(2) . . ? C19 N20 C21 119.9(2) . . ? C15 N20 C21 120.2(2) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 C20 118.3(3) . . ? C17 C18 C20 121.2(2) . . ? N20 C19 C18 124.0(3) . . ? N20 C21 C23 119.3(2) . . ? N20 C21 C22 118.8(2) . . ? C23 C21 C22 60.1(2) . . ? O3 C17 C18 122.3(2) . . ? O3 C17 C14 121.8(2) . . ? C18 C17 C14 115.9(2) . . ? O1 C20 O2 121.7(2) . . ? O1 C20 C18 122.6(3) . . ? O2 C20 C18 115.7(2) . . ? C21 C23 C22 60.26(19) . . ? C23 C22 C21 59.66(19) . . ? C31 P1 C41 103.41(12) . . ? C31 P1 C1 107.94(13) . . ? C41 P1 C1 102.56(13) . . ? C31 P1 S1 112.44(10) . . ? C41 P1 S1 111.07(10) . . ? C1 P1 S1 118.04(10) . . ? C11 N4 C5 118.8(2) . . ? C11 N4 C3 122.1(2) . . ? C5 N4 C3 110.3(2) . . ? C11 C16 C15 121.6(3) . . ? C13 C14 C15 118.1(2) . . ? C13 C14 C17 120.9(2) . . ? C15 C14 C17 121.1(2) . . ? C1 N1 C6 111.8(2) . . ? C1 N1 C2 108.3(2) . . ? C6 N1 C2 108.9(2) . . ? C16 C15 N20 120.4(2) . . ? C16 C15 C14 120.7(2) . . ? N20 C15 C14 118.9(2) . . ? C12 C13 C14 120.1(3) . . ? C13 C12 F12 118.7(3) . . ? C13 C12 C11 123.3(3) . . ? F12 C12 C11 117.8(2) . . ? N4 C5 C6 109.0(2) . . ? N1 C6 C5 110.2(2) . . ? N1 C2 C3 111.4(2) . . ? N4 C11 C16 122.8(3) . . ? N4 C11 C12 120.8(3) . . ? C16 C11 C12 116.1(2) . . ? C36 C31 C32 119.3(3) . . ? C36 C31 P1 117.5(2) . . ? C32 C31 P1 123.0(2) . . ? C46 C41 C42 119.5(3) . . ? C46 C41 P1 122.4(2) . . ? C42 C41 P1 118.0(2) . . ? N1 C1 P1 117.49(19) . . ? N4 C3 C2 109.5(2) . . ? C45 C46 C41 119.9(3) . . ? C44 C45 C46 120.6(3) . . ? C44 C43 C42 120.3(3) . . ? C43 C42 C41 119.8(3) . . ? C35 C36 C31 120.7(3) . . ? C45 C44 C43 119.9(3) . . ? C33 C32 C31 119.6(3) . . ? C33 C34 C35 120.1(3) . . ? C36 C35 C34 119.7(3) . . ? C34 C33 C32 120.5(3) . . ? Cl1 C50 Cl2 109.0(6) 3_566 3_566 ? Cl2 C50 Cl1 112.7(6) . . ? Cl1 C50 Cl1 121.0(5) 3_566 . ? Cl1 Cl2 C50 148.3(9) 3_566 . ? Cl1 Cl2 C50 132.4(9) 3_566 3_566 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 1.77 2.533(3) 153.0 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.720 _refine_diff_density_min -1.235 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 948748' ####################################################################### # # 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_SePCp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H29 F N3 O3 P Se,0.79(C H4 O), 0.11(H2 O)' _chemical_formula_sum 'C30.79 H32.36 F N3 O3.89 P Se' _chemical_formula_weight 635.58 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' F F 0.0171 0.0103 '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' Se Se -0.0929 2.2259 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.102(3) _cell_length_b 25.993(6) _cell_length_c 14.216(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.42(3) _cell_angle_gamma 90.00 _cell_volume 2991.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8534 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 28.70 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308.8 _exptl_absorpt_coefficient_mu 1.355 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.6634 _exptl_absorpt_correction_T_max 0.8436 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k-axis diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18670 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.78 _reflns_number_total 11096 _reflns_number_gt 9934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(5) _refine_ls_number_reflns 11096 _refine_ls_number_parameters 757 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.003 _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 P1A P 0.60578(11) 0.88291(5) 0.81706(6) 0.02013(19) Uani 1 1 d . . . Se1A Se 0.67145(4) 0.94151(3) 0.72304(2) 0.02743(10) Uani 1 1 d . . . C1A C 0.4648(4) 0.83304(14) 0.7685(2) 0.0228(8) Uani 1 1 d . . . H1A1 H 0.4375 0.8088 0.8193 0.027 Uiso 1 1 calc R . . H1A2 H 0.3608 0.8495 0.7451 0.027 Uiso 1 1 calc R . . N1A N 0.5356(3) 0.80458(11) 0.69256(19) 0.0215(6) Uani 1 1 d . . . C2A C 0.4941(4) 0.82836(14) 0.6006(2) 0.0250(8) Uani 1 1 d . . . H2A1 H 0.5295 0.8648 0.6018 0.030 Uiso 1 1 calc R . . H2A2 H 0.3729 0.8275 0.5885 0.030 Uiso 1 1 calc R . . C3A C 0.5774(4) 0.80052(13) 0.5223(2) 0.0230(8) Uani 1 1 d . . . H3A1 H 0.5445 0.8166 0.4612 0.028 Uiso 1 1 calc R . . H3A2 H 0.6988 0.8039 0.5315 0.028 Uiso 1 1 calc R . . N4A N 0.5326(3) 0.74598(12) 0.52009(19) 0.0216(6) Uani 1 1 d . . . C5A C 0.5645(4) 0.72209(14) 0.6134(2) 0.0240(8) Uani 1 1 d . . . H5A1 H 0.6850 0.7215 0.6283 0.029 Uiso 1 1 calc R . . H5A2 H 0.5246 0.6861 0.6118 0.029 Uiso 1 1 calc R . . C6A C 0.4793(4) 0.75120(14) 0.6889(2) 0.0241(8) Uani 1 1 d . . . H6A1 H 0.3584 0.7503 0.6758 0.029 Uiso 1 1 calc R . . H6A2 H 0.5032 0.7346 0.7506 0.029 Uiso 1 1 calc R . . C11A C 0.5757(4) 0.71899(14) 0.4411(2) 0.0218(8) Uani 1 1 d . . . C12A C 0.5220(4) 0.66779(15) 0.4248(2) 0.0255(8) Uani 1 1 d . . . F12A F 0.4198(3) 0.64612(9) 0.48718(15) 0.0356(6) Uani 1 1 d . . . C13A C 0.5599(4) 0.64027(14) 0.3482(2) 0.0247(8) Uani 1 1 d . . . H13A H 0.5216 0.6059 0.3416 0.030 Uiso 1 1 calc R . . C14A C 0.6554(4) 0.66189(15) 0.2783(2) 0.0234(8) Uani 1 1 d . . . C15A C 0.7051(4) 0.71350(14) 0.2902(2) 0.0213(7) Uani 1 1 d . . . C16A C 0.6676(4) 0.74061(14) 0.3712(2) 0.0233(8) Uani 1 1 d . . . H16A H 0.7063 0.7749 0.3787 0.028 Uiso 1 1 calc R . . C17A C 0.6960(4) 0.63291(14) 0.1960(2) 0.0239(8) Uani 1 1 d . . . C18A C 0.7993(4) 0.65953(14) 0.1319(2) 0.0230(8) Uani 1 1 d . . . C19A C 0.8432(4) 0.70902(15) 0.1468(2) 0.0237(8) Uani 1 1 d . . . H19A H 0.9105 0.7252 0.1024 0.028 Uiso 1 1 calc R . . N20A N 0.7970(3) 0.73675(12) 0.22119(19) 0.0214(6) Uani 1 1 d . . . C20A C 0.8571(5) 0.63323(15) 0.0472(3) 0.0270(8) Uani 1 1 d . . . C21A C 0.8428(4) 0.79034(14) 0.2304(2) 0.0240(8) Uani 1 1 d . . . H21A H 0.9330 0.7985 0.2782 0.029 Uiso 1 1 calc R . . C22A C 0.8336(5) 0.82349(14) 0.1454(2) 0.0296(9) Uani 1 1 d . . . H22A H 0.7975 0.8074 0.0849 0.036 Uiso 1 1 calc R . . H22B H 0.9176 0.8509 0.1404 0.036 Uiso 1 1 calc R . . C23A C 0.7088(5) 0.82946(15) 0.2183(2) 0.0285(8) Uani 1 1 d . . . H23A H 0.5953 0.8170 0.2031 0.034 Uiso 1 1 calc R . . H23B H 0.7156 0.8605 0.2586 0.034 Uiso 1 1 calc R . . O1A O 0.9565(3) 0.65188(11) -0.00515(18) 0.0313(6) Uani 1 1 d . . . O2A O 0.7936(3) 0.58674(10) 0.03112(18) 0.0326(6) Uani 1 1 d . . . H2A H 0.7373 0.5780 0.0767 0.049 Uiso 1 1 calc R . . O3A O 0.6457(3) 0.58796(10) 0.18201(17) 0.0285(6) Uani 1 1 d . . . C31A C 0.4909(4) 0.90899(14) 0.9139(2) 0.0209(7) Uani 1 1 d . . . C32A C 0.3764(4) 0.94767(15) 0.8945(2) 0.0255(8) Uani 1 1 d . . . H32A H 0.3630 0.9611 0.8325 0.031 Uiso 1 1 calc R . . C33A C 0.2822(5) 0.96659(15) 0.9654(3) 0.0314(9) Uani 1 1 d . . . H33A H 0.2029 0.9928 0.9518 0.038 Uiso 1 1 calc R . . C34A C 0.3025(4) 0.94767(15) 1.0558(3) 0.0315(9) Uani 1 1 d . . . H34A H 0.2373 0.9608 1.1043 0.038 Uiso 1 1 calc R . . C35A C 0.4173(5) 0.90972(15) 1.0756(3) 0.0303(9) Uani 1 1 d . . . H35A H 0.4327 0.8971 1.1380 0.036 Uiso 1 1 calc R . . C36A C 0.5108(4) 0.88979(13) 1.0041(2) 0.0215(8) Uani 1 1 d . . . H36A H 0.5882 0.8630 1.0174 0.026 Uiso 1 1 calc R . . C41A C 0.7825(4) 0.84797(14) 0.8675(2) 0.0188(7) Uani 1 1 d . . . C42A C 0.7790(4) 0.79497(14) 0.8753(2) 0.0225(8) Uani 1 1 d . . . H42A H 0.6811 0.7764 0.8585 0.027 Uiso 1 1 calc R . . C43A C 0.9196(4) 0.76918(16) 0.9080(2) 0.0270(8) Uani 1 1 d . . . H43A H 0.9182 0.7327 0.9124 0.032 Uiso 1 1 calc R . . C44A C 1.0606(4) 0.79546(16) 0.9341(3) 0.0314(9) Uani 1 1 d . . . H44A H 1.1563 0.7773 0.9564 0.038 Uiso 1 1 calc R . . C45A C 1.0632(4) 0.84788(17) 0.9277(3) 0.0342(9) Uani 1 1 d . . . H45A H 1.1603 0.8662 0.9471 0.041 Uiso 1 1 calc R . . C46A C 0.9258(4) 0.87444(15) 0.8935(2) 0.0266(8) Uani 1 1 d . . . H46A H 0.9295 0.9108 0.8877 0.032 Uiso 1 1 calc R . . P1B P 1.13105(11) 0.89286(5) 0.41509(6) 0.0269(2) Uani 1 1 d . . . Se1B Se 1.27749(6) 0.8586 0.31314(3) 0.0323(2) Uani 0.911(4) 1 d P . . Se2B Se 1.2429(19) 0.8818(7) 0.2954(10) 0.123(5) Uiso 0.089(4) 1 d P . . C1B C 1.2388(4) 0.94657(17) 0.4764(2) 0.0279(8) Uani 1 1 d . . . H1B1 H 1.3297 0.9324 0.5172 0.033 Uiso 1 1 calc R . . H1B2 H 1.2888 0.9689 0.4289 0.033 Uiso 1 1 calc R . . N1B N 1.1336(3) 0.97788(12) 0.53360(19) 0.0248(7) Uani 1 1 d . . . C2B C 1.0837(5) 1.02586(15) 0.4875(2) 0.0293(9) Uani 1 1 d . . . H2B1 H 1.0354 1.0184 0.4238 0.035 Uiso 1 1 calc R . . H2B2 H 1.1817 1.0481 0.4806 0.035 Uiso 1 1 calc R . . C3B C 0.9588(4) 1.05343(15) 0.5444(2) 0.0277(8) Uani 1 1 d . . . H3B1 H 0.9293 1.0866 0.5138 0.033 Uiso 1 1 calc R . . H3B2 H 0.8572 1.0324 0.5467 0.033 Uiso 1 1 calc R . . N4B N 1.0253(4) 1.06304(12) 0.64110(19) 0.0246(7) Uani 1 1 d . . . C5B C 1.0819(4) 1.01524(14) 0.6853(2) 0.0239(8) Uani 1 1 d . . . H5B1 H 0.9868 0.9919 0.6925 0.029 Uiso 1 1 calc R . . H5B2 H 1.1311 1.0226 0.7488 0.029 Uiso 1 1 calc R . . C6B C 1.2079(4) 0.98957(16) 0.6267(2) 0.0277(8) Uani 1 1 d . . . H6B1 H 1.3042 1.0126 0.6204 0.033 Uiso 1 1 calc R . . H6B2 H 1.2468 0.9574 0.6578 0.033 Uiso 1 1 calc R . . C11B C 0.9319(4) 1.09599(15) 0.6954(2) 0.0230(8) Uani 1 1 d . . . C12B C 0.9117(4) 1.14780(15) 0.6696(2) 0.0258(8) Uani 1 1 d . . . F1B F 0.9825(3) 1.16396(9) 0.58992(14) 0.0323(5) Uani 1 1 d . . . C13B C 0.8332(4) 1.18288(15) 0.7213(2) 0.0249(8) Uani 1 1 d . . . H13B H 0.8241 1.2176 0.7007 0.030 Uiso 1 1 calc R . . C14B C 0.7644(4) 1.16743(14) 0.8067(2) 0.0236(8) Uani 1 1 d . . . C15B C 0.7775(4) 1.11575(14) 0.8322(2) 0.0213(8) Uani 1 1 d . . . C16B C 0.8605(4) 1.08069(14) 0.7775(2) 0.0215(7) Uani 1 1 d . . . H16B H 0.8683 1.0457 0.7968 0.026 Uiso 1 1 calc R . . C17B C 0.6823(4) 1.20468(14) 0.8644(3) 0.0262(8) Uani 1 1 d . . . C18B C 0.6132(4) 1.18427(14) 0.9471(2) 0.0232(8) Uani 1 1 d . . . C19B C 0.6232(4) 1.13319(14) 0.9662(2) 0.0225(8) Uani 1 1 d . . . H19B H 0.5709 1.1208 1.0204 0.027 Uiso 1 1 calc R . . N20B N 0.7016(3) 1.09929(12) 0.91395(19) 0.0210(6) Uani 1 1 d . . . C20B C 0.5252(5) 1.21750(15) 1.0128(3) 0.0275(8) Uani 1 1 d . . . C21B C 0.6929(4) 1.04465(14) 0.9337(2) 0.0229(8) Uani 1 1 d . . . H21B H 0.6297 1.0238 0.8853 0.027 Uiso 1 1 calc R . . C22B C 0.8360(5) 1.01838(15) 0.9801(2) 0.0289(8) Uani 1 1 d . . . H22C H 0.9339 1.0395 0.9985 0.035 Uiso 1 1 calc R . . H22D H 0.8610 0.9829 0.9597 0.035 Uiso 1 1 calc R . . C23B C 0.6799(4) 1.02692(14) 1.0323(2) 0.0261(8) Uani 1 1 d . . . H23C H 0.6092 0.9967 1.0438 0.031 Uiso 1 1 calc R . . H23D H 0.6820 1.0533 1.0826 0.031 Uiso 1 1 calc R . . O1B O 0.4631(3) 1.20144(11) 1.08362(19) 0.0377(7) Uani 1 1 d . . . O2B O 0.5162(3) 1.26672(10) 0.9884(2) 0.0368(7) Uani 1 1 d . . . H2B H 0.5621 1.2710 0.9371 0.055 Uiso 1 1 calc R . . O3B O 0.6730(3) 1.25141(10) 0.84247(18) 0.0351(7) Uani 1 1 d . . . C31B C 0.9450(4) 0.92235(15) 0.3667(2) 0.0280(8) Uani 1 1 d . . . C32B C 0.9497(5) 0.9439(2) 0.2785(3) 0.0425(10) Uani 1 1 d . . . H32B H 1.0462 0.9405 0.2433 0.051 Uiso 1 1 calc R . . C33B C 0.8154(6) 0.9704(2) 0.2411(3) 0.0553(13) Uani 1 1 d . . . H33B H 0.8200 0.9858 0.1807 0.066 Uiso 1 1 calc R . . C34B C 0.6754(6) 0.9745(2) 0.2908(4) 0.0565(13) Uani 1 1 d . . . H34B H 0.5817 0.9922 0.2646 0.068 Uiso 1 1 calc R . . C35B C 0.6710(5) 0.95291(19) 0.3785(3) 0.0498(13) Uani 1 1 d . . . H35B H 0.5734 0.9559 0.4129 0.060 Uiso 1 1 calc R . . C36B C 0.8040(4) 0.92723(15) 0.4176(3) 0.0346(10) Uani 1 1 d . . . H36B H 0.7997 0.9129 0.4789 0.042 Uiso 1 1 calc R . . C41B C 1.0733(4) 0.84725(16) 0.5034(2) 0.0251(8) Uani 1 1 d . . . C42B C 1.0889(4) 0.79502(16) 0.4868(3) 0.0304(9) Uani 1 1 d . . . H42B H 1.1242 0.7836 0.4275 0.037 Uiso 1 1 calc R . . C43B C 1.0542(4) 0.75932(16) 0.5549(3) 0.0311(9) Uani 1 1 d . . . H43B H 1.0631 0.7236 0.5422 0.037 Uiso 1 1 calc R . . C44B C 1.0064(4) 0.77612(16) 0.6417(3) 0.0295(9) Uani 1 1 d . . . H44B H 0.9847 0.7518 0.6895 0.035 Uiso 1 1 calc R . . C45B C 0.9900(4) 0.82708(16) 0.6592(2) 0.0290(9) Uani 1 1 d . . . H45B H 0.9563 0.8381 0.7191 0.035 Uiso 1 1 calc R . . C46B C 1.0219(4) 0.86321(16) 0.5911(2) 0.0263(8) Uani 1 1 d . . . H46B H 1.0087 0.8988 0.6039 0.032 Uiso 1 1 calc R . . O2S O 1.0745(8) 0.60420(18) -0.1624(3) 0.0821(19) Uani 0.785(5) 1 d P A 1 H2S H 1.0773 0.6149 -0.1066 0.123 Uiso 0.785(5) 1 calc PR A 1 C2S C 1.1406(12) 0.6413(3) -0.2202(5) 0.102(4) Uani 0.785(5) 1 d P A 1 H2S1 H 1.2281 0.6250 -0.2544 0.153 Uiso 0.785(5) 1 d PR A 1 H2S2 H 1.1807 0.6691 -0.1816 0.153 Uiso 0.785(5) 1 d PR A 1 H2S3 H 1.0519 0.6527 -0.2647 0.153 Uiso 0.785(5) 1 d PR A 1 O1S O 0.7772(10) 0.5501(3) -0.2399(5) 0.124(3) Uani 0.785(5) 1 d P A 1 H1S H 0.8699 0.5628 -0.2249 0.186 Uiso 0.785(5) 1 calc PR A 1 C1S C 0.6583(13) 0.5858(4) -0.2283(8) 0.122(4) Uani 0.785(5) 1 d P A 1 H1S1 H 0.6052 0.5896 -0.2879 0.183 Uiso 0.785(5) 1 d PR A 1 H1S2 H 0.7183 0.6158 -0.2063 0.183 Uiso 0.785(5) 1 d PR A 1 H1S3 H 0.5876 0.5724 -0.1807 0.183 Uiso 0.785(5) 1 d PR A 1 O1W O 0.917(2) 0.6300(5) -0.2918(11) 0.058(6) Uani 0.215(5) 1 d P A 2 H1W H 0.9490 0.6091 -0.2528 0.087 Uiso 0.215(5) 1 d PR A 2 H3W H 0.8462 0.6115 -0.3182 0.087 Uiso 0.215(5) 1 d PR 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 P1A 0.0172(4) 0.0249(5) 0.0185(4) -0.0011(4) 0.0045(3) 0.0000(4) Se1A 0.0290(2) 0.02924(19) 0.02477(18) 0.00277(18) 0.00941(14) -0.00249(18) C1A 0.0188(18) 0.030(2) 0.0193(16) 0.0007(15) 0.0006(13) -0.0005(16) N1A 0.0198(15) 0.0246(15) 0.0202(14) -0.0002(13) 0.0010(11) 0.0003(13) C2A 0.0257(19) 0.0268(19) 0.0221(17) -0.0037(16) -0.0026(15) 0.0026(17) C3A 0.0240(19) 0.0253(19) 0.0197(17) 0.0006(15) 0.0013(14) 0.0031(16) N4A 0.0242(16) 0.0230(15) 0.0175(14) -0.0026(13) -0.0013(12) 0.0011(14) C5A 0.0242(19) 0.0240(19) 0.0234(17) -0.0008(16) -0.0023(15) -0.0001(16) C6A 0.0223(19) 0.027(2) 0.0227(17) 0.0008(16) -0.0004(14) -0.0010(16) C11A 0.0178(18) 0.0292(19) 0.0182(16) -0.0009(15) -0.0043(13) 0.0049(16) C12A 0.024(2) 0.031(2) 0.0217(18) 0.0030(17) -0.0034(15) -0.0026(18) F12A 0.0360(14) 0.0425(13) 0.0286(12) -0.0049(10) 0.0056(10) -0.0129(12) C13A 0.022(2) 0.024(2) 0.028(2) -0.0032(17) -0.0058(15) 0.0013(16) C14A 0.0179(19) 0.030(2) 0.0217(18) 0.0010(17) -0.0046(14) 0.0034(16) C15A 0.0153(17) 0.0275(19) 0.0208(17) -0.0018(16) -0.0045(14) 0.0039(16) C16A 0.0206(18) 0.0245(18) 0.0245(17) -0.0044(16) -0.0052(14) 0.0026(16) C17A 0.0180(19) 0.026(2) 0.0264(18) -0.0049(17) -0.0109(14) 0.0044(17) C18A 0.0193(19) 0.028(2) 0.0215(18) -0.0063(16) -0.0061(14) 0.0051(17) C19A 0.0167(18) 0.032(2) 0.0217(17) -0.0004(16) -0.0021(14) 0.0081(16) N20A 0.0178(15) 0.0259(16) 0.0200(14) -0.0034(13) -0.0029(11) 0.0024(14) C20A 0.026(2) 0.029(2) 0.0252(19) -0.0030(17) -0.0081(16) 0.0109(18) C21A 0.0267(19) 0.0264(19) 0.0184(16) -0.0071(16) -0.0035(14) 0.0008(17) C22A 0.038(2) 0.0255(19) 0.0252(19) -0.0035(17) 0.0024(16) 0.0038(18) C23A 0.033(2) 0.0270(19) 0.0250(18) -0.0056(16) -0.0008(16) 0.0071(18) O1A 0.0354(17) 0.0334(14) 0.0250(14) -0.0040(12) 0.0021(12) 0.0073(13) O2A 0.0387(17) 0.0299(15) 0.0290(14) -0.0076(13) -0.0002(12) 0.0032(13) O3A 0.0298(14) 0.0260(14) 0.0291(13) -0.0068(12) -0.0059(11) 0.0002(12) C31A 0.0130(16) 0.0237(18) 0.0266(18) -0.0038(15) 0.0065(14) -0.0019(15) C32A 0.0224(18) 0.026(2) 0.0285(18) 0.0042(17) 0.0053(14) 0.0005(17) C33A 0.025(2) 0.0241(19) 0.046(2) 0.0018(18) 0.0116(17) 0.0050(17) C34A 0.028(2) 0.029(2) 0.039(2) -0.0047(19) 0.0214(16) 0.0023(19) C35A 0.032(2) 0.034(2) 0.0258(19) 0.0006(17) 0.0122(16) -0.0080(19) C36A 0.0186(18) 0.0218(19) 0.0246(17) 0.0018(16) 0.0056(14) 0.0041(16) C41A 0.0154(16) 0.0260(18) 0.0152(14) -0.0038(15) 0.0041(12) 0.0012(15) C42A 0.0212(18) 0.0292(19) 0.0174(16) 0.0011(16) 0.0025(13) 0.0005(17) C43A 0.028(2) 0.031(2) 0.0219(17) 0.0030(16) 0.0035(15) 0.0004(18) C44A 0.021(2) 0.042(2) 0.032(2) -0.0016(19) -0.0008(16) 0.0067(18) C45A 0.0140(18) 0.049(3) 0.039(2) -0.009(2) -0.0005(15) 0.0006(19) C46A 0.0206(18) 0.0257(19) 0.0340(19) -0.0045(16) 0.0063(15) -0.0019(16) P1B 0.0203(5) 0.0442(6) 0.0164(4) -0.0008(4) 0.0039(3) 0.0008(5) Se1B 0.0269(3) 0.0538(4) 0.0170(2) -0.0035(2) 0.01037(16) 0.0078(2) C1B 0.0193(17) 0.044(2) 0.0206(16) 0.0002(19) 0.0035(13) 0.0024(19) N1B 0.0195(15) 0.0342(17) 0.0206(14) -0.0013(14) -0.0003(12) -0.0018(14) C2B 0.027(2) 0.040(2) 0.0206(18) 0.0034(18) 0.0015(15) -0.0026(19) C3B 0.027(2) 0.036(2) 0.0197(17) 0.0052(17) -0.0031(14) -0.0003(18) N4B 0.0226(16) 0.0321(17) 0.0188(14) 0.0025(14) 0.0000(12) -0.0003(14) C5B 0.0220(19) 0.031(2) 0.0187(17) 0.0008(16) -0.0003(14) -0.0015(17) C6B 0.0216(19) 0.037(2) 0.0246(18) 0.0022(17) 0.0017(15) -0.0009(17) C11B 0.0176(18) 0.033(2) 0.0182(17) 0.0008(16) -0.0040(14) -0.0049(17) C12B 0.023(2) 0.035(2) 0.0193(18) 0.0073(16) -0.0049(15) -0.0087(17) F1B 0.0318(12) 0.0399(13) 0.0253(11) 0.0121(10) 0.0038(9) -0.0073(11) C13B 0.0193(19) 0.0259(19) 0.0288(19) 0.0062(17) -0.0081(15) -0.0040(16) C14B 0.0166(18) 0.0286(19) 0.0252(18) 0.0038(17) -0.0060(14) -0.0027(16) C15B 0.0159(18) 0.028(2) 0.0200(17) 0.0004(16) -0.0052(14) -0.0039(16) C16B 0.0187(18) 0.0222(18) 0.0235(17) 0.0016(15) -0.0013(14) -0.0035(16) C17B 0.0195(19) 0.025(2) 0.033(2) -0.0014(18) -0.0100(16) -0.0020(17) C18B 0.0205(19) 0.0225(18) 0.0258(18) 0.0001(16) -0.0081(14) -0.0004(16) C19B 0.0169(18) 0.029(2) 0.0210(17) 0.0029(16) -0.0017(14) -0.0021(16) N20B 0.0175(15) 0.0227(16) 0.0226(14) 0.0000(13) 0.0003(12) -0.0018(13) C20B 0.023(2) 0.024(2) 0.034(2) -0.0021(18) -0.0090(16) 0.0054(17) C21B 0.028(2) 0.0208(17) 0.0203(17) -0.0004(15) 0.0052(15) -0.0047(16) C22B 0.030(2) 0.0253(19) 0.032(2) 0.0053(17) 0.0063(16) 0.0039(18) C23B 0.027(2) 0.0237(18) 0.0276(19) -0.0007(16) 0.0070(15) 0.0060(17) O1B 0.0452(18) 0.0321(16) 0.0363(16) -0.0062(13) 0.0070(13) 0.0092(14) O2B 0.0385(17) 0.0255(14) 0.0467(18) -0.0027(13) 0.0030(14) 0.0059(13) O3B 0.0391(16) 0.0224(14) 0.0433(16) 0.0044(13) -0.0028(13) 0.0017(13) C31B 0.0252(19) 0.035(2) 0.0238(18) -0.0006(17) -0.0052(15) -0.0024(17) C32B 0.041(2) 0.057(3) 0.029(2) 0.011(2) -0.0023(17) -0.002(3) C33B 0.064(3) 0.061(3) 0.041(3) 0.018(2) -0.008(2) 0.011(3) C34B 0.044(3) 0.054(3) 0.069(3) 0.009(3) -0.019(3) 0.009(3) C35B 0.027(2) 0.062(3) 0.060(3) 0.009(3) 0.002(2) 0.009(2) C36B 0.026(2) 0.040(2) 0.038(2) 0.0064(19) 0.0039(17) 0.0004(18) C41B 0.0183(18) 0.041(2) 0.0154(15) -0.0010(17) -0.0018(13) 0.0031(17) C42B 0.0211(19) 0.046(2) 0.0234(18) -0.0104(18) -0.0034(15) 0.0011(19) C43B 0.025(2) 0.033(2) 0.034(2) -0.0045(19) -0.0108(16) 0.0008(18) C44B 0.022(2) 0.040(2) 0.0255(18) 0.0049(18) -0.0014(15) 0.0004(18) C45B 0.024(2) 0.041(2) 0.0224(18) -0.0037(18) 0.0053(15) -0.0020(19) C46B 0.0192(17) 0.037(2) 0.0228(16) -0.0054(18) 0.0034(13) 0.0009(18) O2S 0.144(5) 0.068(3) 0.036(3) 0.006(2) 0.027(3) 0.041(3) C2S 0.158(10) 0.106(7) 0.045(4) 0.022(5) 0.038(5) 0.042(7) O1S 0.203(8) 0.086(4) 0.084(5) -0.017(4) 0.026(5) -0.031(5) C1S 0.149(10) 0.083(7) 0.138(9) -0.013(7) 0.044(8) 0.027(7) O1W 0.090(13) 0.019(7) 0.068(10) -0.019(7) 0.049(9) -0.007(8) _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 P1A C41A 1.817(3) . ? P1A C31A 1.825(3) . ? P1A C1A 1.842(4) . ? P1A Se1A 2.1094(10) . ? C1A N1A 1.447(4) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? N1A C6A 1.461(4) . ? N1A C2A 1.472(4) . ? C2A C3A 1.511(4) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A N4A 1.463(4) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? N4A C11A 1.381(4) . ? N4A C5A 1.478(4) . ? C5A C6A 1.504(4) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C11A C16A 1.386(5) . ? C11A C12A 1.416(5) . ? C12A C13A 1.349(5) . ? C12A F12A 1.360(4) . ? C13A C14A 1.403(5) . ? C13A H13A 0.9500 . ? C14A C15A 1.409(5) . ? C14A C17A 1.441(5) . ? C15A N20A 1.394(4) . ? C15A C16A 1.395(5) . ? C16A H16A 0.9500 . ? C17A O3A 1.251(4) . ? C17A C18A 1.440(5) . ? C18A C19A 1.349(5) . ? C18A C20A 1.479(5) . ? C19A N20A 1.346(4) . ? C19A H19A 0.9500 . ? N20A C21A 1.446(4) . ? C20A O1A 1.219(4) . ? C20A O2A 1.329(4) . ? C21A C22A 1.483(5) . ? C21A C23A 1.492(5) . ? C21A H21A 1.0000 . ? C22A C23A 1.486(5) . ? C22A H22A 0.9900 . ? C22A H22B 0.9900 . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? O2A H2A 0.8400 . ? C31A C36A 1.379(5) . ? C31A C32A 1.387(5) . ? C32A C33A 1.380(5) . ? C32A H32A 0.9500 . ? C33A C34A 1.380(5) . ? C33A H33A 0.9500 . ? C34A C35A 1.377(5) . ? C34A H34A 0.9500 . ? C35A C36A 1.393(5) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? C41A C42A 1.382(5) . ? C41A C46A 1.386(5) . ? C42A C43A 1.385(5) . ? C42A H42A 0.9500 . ? C43A C44A 1.369(5) . ? C43A H43A 0.9500 . ? C44A C45A 1.366(6) . ? C44A H44A 0.9500 . ? C45A C46A 1.382(5) . ? C45A H45A 0.9500 . ? C46A H46A 0.9500 . ? P1B C31B 1.801(4) . ? P1B C41B 1.802(4) . ? P1B C1B 1.846(4) . ? P1B Se2B 1.982(12) . ? P1B Se1B 2.1088(12) . ? Se1B Se2B 0.71(2) . ? C1B N1B 1.452(4) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? N1B C2B 1.458(5) . ? N1B C6B 1.463(4) . ? C2B C3B 1.503(5) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B N4B 1.476(4) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? N4B C11B 1.397(4) . ? N4B C5B 1.458(5) . ? C5B C6B 1.501(5) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C11B C16B 1.383(5) . ? C11B C12B 1.403(5) . ? C12B C13B 1.348(5) . ? C12B F1B 1.358(4) . ? C13B C14B 1.415(5) . ? C13B H13B 0.9500 . ? C14B C15B 1.394(5) . ? C14B C17B 1.449(5) . ? C15B C16B 1.390(5) . ? C15B N20B 1.404(4) . ? C16B H16B 0.9500 . ? C17B O3B 1.256(4) . ? C17B C18B 1.426(5) . ? C18B C19B 1.357(5) . ? C18B C20B 1.478(5) . ? C19B N20B 1.331(4) . ? C19B H19B 0.9500 . ? N20B C21B 1.450(4) . ? C20B O1B 1.218(4) . ? C20B O2B 1.327(4) . ? C21B C22B 1.477(5) . ? C21B C23B 1.484(5) . ? C21B H21B 1.0000 . ? C22B C23B 1.510(5) . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? O2B H2B 0.8400 . ? C31B C32B 1.375(5) . ? C31B C36B 1.383(5) . ? C32B C33B 1.375(6) . ? C32B H32B 0.9500 . ? C33B C34B 1.365(7) . ? C33B H33B 0.9500 . ? C34B C35B 1.370(6) . ? C34B H34B 0.9500 . ? C35B C36B 1.365(5) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? C41B C42B 1.384(5) . ? C41B C46B 1.395(4) . ? C42B C43B 1.378(5) . ? C42B H42B 0.9500 . ? C43B C44B 1.380(5) . ? C43B H43B 0.9500 . ? C44B C45B 1.355(5) . ? C44B H44B 0.9500 . ? C45B C46B 1.381(5) . ? C45B H45B 0.9500 . ? C46B H46B 0.9500 . ? O2S C2S 1.389(9) . ? O2S H2S 0.8400 . ? C2S H2S1 0.9725 . ? C2S H2S2 0.9558 . ? C2S H2S3 0.9833 . ? O1S C1S 1.353(10) . ? O1S H1S 0.8400 . ? C1S H1S1 0.9384 . ? C1S H1S2 0.9637 . ? C1S H1S3 0.9703 . ? O1W H2S3 1.2895 . ? O1W H1W 0.8122 . ? O1W H3W 0.8235 . ? 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 C41A P1A C31A 107.86(15) . . ? C41A P1A C1A 105.19(16) . . ? C31A P1A C1A 102.48(15) . . ? C41A P1A Se1A 113.27(11) . . ? C31A P1A Se1A 111.10(12) . . ? C1A P1A Se1A 116.08(11) . . ? N1A C1A P1A 112.3(2) . . ? N1A C1A H1A1 109.1 . . ? P1A C1A H1A1 109.1 . . ? N1A C1A H1A2 109.1 . . ? P1A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.9 . . ? C1A N1A C6A 112.3(3) . . ? C1A N1A C2A 111.4(3) . . ? C6A N1A C2A 107.9(3) . . ? N1A C2A C3A 111.2(3) . . ? N1A C2A H2A1 109.4 . . ? C3A C2A H2A1 109.4 . . ? N1A C2A H2A2 109.4 . . ? C3A C2A H2A2 109.4 . . ? H2A1 C2A H2A2 108.0 . . ? N4A C3A C2A 111.2(3) . . ? N4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? N4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? C11A N4A C3A 116.0(3) . . ? C11A N4A C5A 118.4(3) . . ? C3A N4A C5A 110.7(3) . . ? N4A C5A C6A 111.1(3) . . ? N4A C5A H5A1 109.4 . . ? C6A C5A H5A1 109.4 . . ? N4A C5A H5A2 109.4 . . ? C6A C5A H5A2 109.4 . . ? H5A1 C5A H5A2 108.0 . . ? N1A C6A C5A 110.6(3) . . ? N1A C6A H6A1 109.5 . . ? C5A C6A H6A1 109.5 . . ? N1A C6A H6A2 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.1 . . ? N4A C11A C16A 122.6(3) . . ? N4A C11A C12A 121.6(3) . . ? C16A C11A C12A 115.7(3) . . ? C13A C12A F12A 118.2(3) . . ? C13A C12A C11A 123.5(3) . . ? F12A C12A C11A 118.3(3) . . ? C12A C13A C14A 120.7(3) . . ? C12A C13A H13A 119.6 . . ? C14A C13A H13A 119.6 . . ? C13A C14A C15A 117.3(3) . . ? C13A C14A C17A 121.2(3) . . ? C15A C14A C17A 121.5(3) . . ? N20A C15A C16A 120.2(3) . . ? N20A C15A C14A 119.1(3) . . ? C16A C15A C14A 120.6(3) . . ? C11A C16A C15A 122.0(3) . . ? C11A C16A H16A 119.0 . . ? C15A C16A H16A 119.0 . . ? O3A C17A C18A 122.9(3) . . ? O3A C17A C14A 122.2(3) . . ? C18A C17A C14A 114.9(3) . . ? C19A C18A C17A 121.0(3) . . ? C19A C18A C20A 118.6(3) . . ? C17A C18A C20A 120.4(3) . . ? N20A C19A C18A 123.6(3) . . ? N20A C19A H19A 118.2 . . ? C18A C19A H19A 118.2 . . ? C19A N20A C15A 119.7(3) . . ? C19A N20A C21A 120.5(3) . . ? C15A N20A C21A 119.8(3) . . ? O1A C20A O2A 121.2(3) . . ? O1A C20A C18A 123.6(4) . . ? O2A C20A C18A 115.3(3) . . ? N20A C21A C22A 118.8(3) . . ? N20A C21A C23A 117.6(3) . . ? C22A C21A C23A 59.9(2) . . ? N20A C21A H21A 116.2 . . ? C22A C21A H21A 116.2 . . ? C23A C21A H21A 116.2 . . ? C21A C22A C23A 60.4(2) . . ? C21A C22A H22A 117.7 . . ? C23A C22A H22A 117.7 . . ? C21A C22A H22B 117.7 . . ? C23A C22A H22B 117.7 . . ? H22A C22A H22B 114.9 . . ? C22A C23A C21A 59.7(2) . . ? C22A C23A H23A 117.8 . . ? C21A C23A H23A 117.8 . . ? C22A C23A H23B 117.8 . . ? C21A C23A H23B 117.8 . . ? H23A C23A H23B 114.9 . . ? C20A O2A H2A 109.5 . . ? C36A C31A C32A 119.9(3) . . ? C36A C31A P1A 121.6(3) . . ? C32A C31A P1A 118.5(3) . . ? C33A C32A C31A 119.9(3) . . ? C33A C32A H32A 120.0 . . ? C31A C32A H32A 120.0 . . ? C34A C33A C32A 120.4(3) . . ? C34A C33A H33A 119.8 . . ? C32A C33A H33A 119.8 . . ? C35A C34A C33A 119.9(3) . . ? C35A C34A H34A 120.0 . . ? C33A C34A H34A 120.0 . . ? C34A C35A C36A 120.1(3) . . ? C34A C35A H35A 120.0 . . ? C36A C35A H35A 120.0 . . ? C31A C36A C35A 119.8(3) . . ? C31A C36A H36A 120.1 . . ? C35A C36A H36A 120.1 . . ? C42A C41A C46A 119.6(3) . . ? C42A C41A P1A 120.7(3) . . ? C46A C41A P1A 119.6(3) . . ? C41A C42A C43A 119.3(3) . . ? C41A C42A H42A 120.3 . . ? C43A C42A H42A 120.3 . . ? C44A C43A C42A 121.0(4) . . ? C44A C43A H43A 119.5 . . ? C42A C43A H43A 119.5 . . ? C45A C44A C43A 119.7(4) . . ? C45A C44A H44A 120.2 . . ? C43A C44A H44A 120.2 . . ? C44A C45A C46A 120.5(4) . . ? C44A C45A H45A 119.8 . . ? C46A C45A H45A 119.8 . . ? C45A C46A C41A 119.9(3) . . ? C45A C46A H46A 120.0 . . ? C41A C46A H46A 120.0 . . ? C31B P1B C41B 107.94(17) . . ? C31B P1B C1B 103.27(18) . . ? C41B P1B C1B 107.47(16) . . ? C31B P1B Se2B 98.0(6) . . ? C41B P1B Se2B 130.1(6) . . ? C1B P1B Se2B 106.9(4) . . ? C31B P1B Se1B 113.81(12) . . ? C41B P1B Se1B 111.76(13) . . ? C1B P1B Se1B 112.06(11) . . ? Se2B P1B Se1B 19.6(6) . . ? Se2B Se1B P1B 70.1(10) . . ? Se1B Se2B P1B 90.3(12) . . ? N1B C1B P1B 114.3(2) . . ? N1B C1B H1B1 108.7 . . ? P1B C1B H1B1 108.7 . . ? N1B C1B H1B2 108.7 . . ? P1B C1B H1B2 108.7 . . ? H1B1 C1B H1B2 107.6 . . ? C1B N1B C2B 112.7(3) . . ? C1B N1B C6B 113.2(3) . . ? C2B N1B C6B 108.9(3) . . ? N1B C2B C3B 110.2(3) . . ? N1B C2B H2B1 109.6 . . ? C3B C2B H2B1 109.6 . . ? N1B C2B H2B2 109.6 . . ? C3B C2B H2B2 109.6 . . ? H2B1 C2B H2B2 108.1 . . ? N4B C3B C2B 110.7(3) . . ? N4B C3B H3B1 109.5 . . ? C2B C3B H3B1 109.5 . . ? N4B C3B H3B2 109.5 . . ? C2B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 108.1 . . ? C11B N4B C5B 116.9(3) . . ? C11B N4B C3B 115.7(3) . . ? C5B N4B C3B 110.7(3) . . ? N4B C5B C6B 110.4(3) . . ? N4B C5B H5B1 109.6 . . ? C6B C5B H5B1 109.6 . . ? N4B C5B H5B2 109.6 . . ? C6B C5B H5B2 109.6 . . ? H5B1 C5B H5B2 108.1 . . ? N1B C6B C5B 109.3(3) . . ? N1B C6B H6B1 109.8 . . ? C5B C6B H6B1 109.8 . . ? N1B C6B H6B2 109.8 . . ? C5B C6B H6B2 109.8 . . ? H6B1 C6B H6B2 108.3 . . ? C16B C11B N4B 123.1(3) . . ? C16B C11B C12B 116.7(3) . . ? N4B C11B C12B 120.2(3) . . ? C13B C12B F1B 118.1(3) . . ? C13B C12B C11B 124.0(3) . . ? F1B C12B C11B 117.8(3) . . ? C12B C13B C14B 119.2(3) . . ? C12B C13B H13B 120.4 . . ? C14B C13B H13B 120.4 . . ? C15B C14B C13B 117.9(3) . . ? C15B C14B C17B 121.9(3) . . ? C13B C14B C17B 120.2(3) . . ? C16B C15B C14B 121.3(3) . . ? C16B C15B N20B 120.1(3) . . ? C14B C15B N20B 118.5(3) . . ? C11B C16B C15B 120.9(3) . . ? C11B C16B H16B 119.6 . . ? C15B C16B H16B 119.6 . . ? O3B C17B C18B 122.9(3) . . ? O3B C17B C14B 122.0(3) . . ? C18B C17B C14B 115.1(3) . . ? C19B C18B C17B 120.5(3) . . ? C19B C18B C20B 118.1(3) . . ? C17B C18B C20B 121.4(3) . . ? N20B C19B C18B 124.1(3) . . ? N20B C19B H19B 117.9 . . ? C18B C19B H19B 117.9 . . ? C19B N20B C15B 119.7(3) . . ? C19B N20B C21B 120.8(3) . . ? C15B N20B C21B 119.0(3) . . ? O1B C20B O2B 121.8(3) . . ? O1B C20B C18B 123.3(3) . . ? O2B C20B C18B 114.9(3) . . ? N20B C21B C22B 119.7(3) . . ? N20B C21B C23B 119.5(3) . . ? C22B C21B C23B 61.3(2) . . ? N20B C21B H21B 115.2 . . ? C22B C21B H21B 115.2 . . ? C23B C21B H21B 115.2 . . ? C21B C22B C23B 59.6(2) . . ? C21B C22B H22C 117.8 . . ? C23B C22B H22C 117.8 . . ? C21B C22B H22D 117.8 . . ? C23B C22B H22D 117.8 . . ? H22C C22B H22D 115.0 . . ? C21B C23B C22B 59.1(2) . . ? C21B C23B H23C 117.9 . . ? C22B C23B H23C 117.9 . . ? C21B C23B H23D 117.9 . . ? C22B C23B H23D 117.9 . . ? H23C C23B H23D 115.0 . . ? C20B O2B H2B 109.5 . . ? C32B C31B C36B 119.6(4) . . ? C32B C31B P1B 117.8(3) . . ? C36B C31B P1B 122.4(3) . . ? C33B C32B C31B 120.3(4) . . ? C33B C32B H32B 119.9 . . ? C31B C32B H32B 119.9 . . ? C34B C33B C32B 120.1(4) . . ? C34B C33B H33B 120.0 . . ? C32B C33B H33B 120.0 . . ? C33B C34B C35B 119.5(4) . . ? C33B C34B H34B 120.2 . . ? C35B C34B H34B 120.2 . . ? C36B C35B C34B 121.3(4) . . ? C36B C35B H35B 119.3 . . ? C34B C35B H35B 119.3 . . ? C35B C36B C31B 119.2(4) . . ? C35B C36B H36B 120.4 . . ? C31B C36B H36B 120.4 . . ? C42B C41B C46B 118.4(3) . . ? C42B C41B P1B 119.9(3) . . ? C46B C41B P1B 121.5(3) . . ? C43B C42B C41B 121.2(3) . . ? C43B C42B H42B 119.4 . . ? C41B C42B H42B 119.4 . . ? C42B C43B C44B 119.2(4) . . ? C42B C43B H43B 120.4 . . ? C44B C43B H43B 120.4 . . ? C45B C44B C43B 120.5(4) . . ? C45B C44B H44B 119.8 . . ? C43B C44B H44B 119.8 . . ? C44B C45B C46B 120.9(3) . . ? C44B C45B H45B 119.6 . . ? C46B C45B H45B 119.6 . . ? C45B C46B C41B 119.8(4) . . ? C45B C46B H46B 120.1 . . ? C41B C46B H46B 120.1 . . ? O2S C2S H2S1 107.5 . . ? O2S C2S H2S2 108.3 . . ? H2S1 C2S H2S2 112.2 . . ? O2S C2S H2S3 107.6 . . ? H2S1 C2S H2S3 109.8 . . ? H2S2 C2S H2S3 111.2 . . ? O1S C1S H1S1 105.2 . . ? O1S C1S H1S2 104.0 . . ? H1S1 C1S H1S2 114.5 . . ? O1S C1S H1S3 106.4 . . ? H1S1 C1S H1S3 113.9 . . ? H1S2 C1S H1S3 111.7 . . ? H2S3 O1W H1W 81.7 . . ? H2S3 O1W H3W 165.2 . . ? H1W O1W H3W 96.8 . . ? 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 C41A P1A C1A N1A -64.0(3) . . . . ? C31A P1A C1A N1A -176.7(2) . . . . ? Se1A P1A C1A N1A 62.1(3) . . . . ? P1A C1A N1A C6A 147.9(2) . . . . ? P1A C1A N1A C2A -90.9(3) . . . . ? C1A N1A C2A C3A 176.3(3) . . . . ? C6A N1A C2A C3A -60.0(4) . . . . ? N1A C2A C3A N4A 57.2(4) . . . . ? C2A C3A N4A C11A 168.1(3) . . . . ? C2A C3A N4A C5A -53.3(4) . . . . ? C11A N4A C5A C6A -168.2(3) . . . . ? C3A N4A C5A C6A 54.3(4) . . . . ? C1A N1A C6A C5A -176.1(3) . . . . ? C2A N1A C6A C5A 60.7(3) . . . . ? N4A C5A C6A N1A -58.9(4) . . . . ? C3A N4A C11A C16A 5.1(5) . . . . ? C5A N4A C11A C16A -130.2(4) . . . . ? C3A N4A C11A C12A -172.2(3) . . . . ? C5A N4A C11A C12A 52.5(4) . . . . ? N4A C11A C12A C13A 179.3(3) . . . . ? C16A C11A C12A C13A 1.9(5) . . . . ? N4A C11A C12A F12A 2.8(5) . . . . ? C16A C11A C12A F12A -174.6(3) . . . . ? F12A C12A C13A C14A 175.6(3) . . . . ? C11A C12A C13A C14A -0.9(6) . . . . ? C12A C13A C14A C15A -1.8(5) . . . . ? C12A C13A C14A C17A -179.7(3) . . . . ? C13A C14A C15A N20A -178.6(3) . . . . ? C17A C14A C15A N20A -0.7(5) . . . . ? C13A C14A C15A C16A 3.4(5) . . . . ? C17A C14A C15A C16A -178.6(3) . . . . ? N4A C11A C16A C15A -177.6(3) . . . . ? C12A C11A C16A C15A -0.2(5) . . . . ? N20A C15A C16A C11A 179.6(3) . . . . ? C14A C15A C16A C11A -2.5(5) . . . . ? C13A C14A C17A O3A 1.6(5) . . . . ? C15A C14A C17A O3A -176.2(3) . . . . ? C13A C14A C17A C18A -178.0(3) . . . . ? C15A C14A C17A C18A 4.2(5) . . . . ? O3A C17A C18A C19A 176.2(3) . . . . ? C14A C17A C18A C19A -4.2(5) . . . . ? O3A C17A C18A C20A -2.7(5) . . . . ? C14A C17A C18A C20A 176.9(3) . . . . ? C17A C18A C19A N20A 0.7(5) . . . . ? C20A C18A C19A N20A 179.6(3) . . . . ? C18A C19A N20A C15A 3.2(5) . . . . ? C18A C19A N20A C21A -177.3(3) . . . . ? C16A C15A N20A C19A 174.9(3) . . . . ? C14A C15A N20A C19A -3.1(5) . . . . ? C16A C15A N20A C21A -4.7(5) . . . . ? C14A C15A N20A C21A 177.3(3) . . . . ? C19A C18A C20A O1A 8.0(5) . . . . ? C17A C18A C20A O1A -173.1(3) . . . . ? C19A C18A C20A O2A -172.4(3) . . . . ? C17A C18A C20A O2A 6.5(5) . . . . ? C19A N20A C21A C22A 41.2(5) . . . . ? C15A N20A C21A C22A -139.2(3) . . . . ? C19A N20A C21A C23A 110.3(3) . . . . ? C15A N20A C21A C23A -70.1(4) . . . . ? N20A C21A C22A C23A 107.0(4) . . . . ? N20A C21A C23A C22A -109.0(3) . . . . ? C41A P1A C31A C36A -18.8(3) . . . . ? C1A P1A C31A C36A 91.9(3) . . . . ? Se1A P1A C31A C36A -143.5(3) . . . . ? C41A P1A C31A C32A 163.7(3) . . . . ? C1A P1A C31A C32A -85.6(3) . . . . ? Se1A P1A C31A C32A 39.0(3) . . . . ? C36A C31A C32A C33A -0.4(5) . . . . ? P1A C31A C32A C33A 177.1(3) . . . . ? C31A C32A C33A C34A 0.8(6) . . . . ? C32A C33A C34A C35A 0.0(6) . . . . ? C33A C34A C35A C36A -1.1(6) . . . . ? C32A C31A C36A C35A -0.7(5) . . . . ? P1A C31A C36A C35A -178.1(3) . . . . ? C34A C35A C36A C31A 1.5(5) . . . . ? C31A P1A C41A C42A 99.8(3) . . . . ? C1A P1A C41A C42A -9.0(3) . . . . ? Se1A P1A C41A C42A -136.8(2) . . . . ? C31A P1A C41A C46A -83.8(3) . . . . ? C1A P1A C41A C46A 167.3(3) . . . . ? Se1A P1A C41A C46A 39.5(3) . . . . ? C46A C41A C42A C43A -0.8(5) . . . . ? P1A C41A C42A C43A 175.5(2) . . . . ? C41A C42A C43A C44A 1.1(5) . . . . ? C42A C43A C44A C45A -0.1(5) . . . . ? C43A C44A C45A C46A -1.3(6) . . . . ? C44A C45A C46A C41A 1.7(5) . . . . ? C42A C41A C46A C45A -0.6(5) . . . . ? P1A C41A C46A C45A -177.0(3) . . . . ? C31B P1B Se1B Se2B 38.4(12) . . . . ? C41B P1B Se1B Se2B 161.0(12) . . . . ? C1B P1B Se1B Se2B -78.3(12) . . . . ? C31B P1B Se2B Se1B -144.9(11) . . . . ? C41B P1B Se2B Se1B -23.3(14) . . . . ? C1B P1B Se2B Se1B 108.5(10) . . . . ? C31B P1B C1B N1B 45.6(3) . . . . ? C41B P1B C1B N1B -68.4(3) . . . . ? Se2B P1B C1B N1B 148.4(7) . . . . ? Se1B P1B C1B N1B 168.5(2) . . . . ? P1B C1B N1B C2B -100.9(3) . . . . ? P1B C1B N1B C6B 134.8(3) . . . . ? C1B N1B C2B C3B 173.0(3) . . . . ? C6B N1B C2B C3B -60.5(4) . . . . ? N1B C2B C3B N4B 56.9(4) . . . . ? C2B C3B N4B C11B 169.5(3) . . . . ? C2B C3B N4B C5B -54.7(4) . . . . ? C11B N4B C5B C6B -168.3(3) . . . . ? C3B N4B C5B C6B 56.4(4) . . . . ? C1B N1B C6B C5B -171.9(3) . . . . ? C2B N1B C6B C5B 61.9(4) . . . . ? N4B C5B C6B N1B -60.3(4) . . . . ? C5B N4B C11B C16B -15.3(5) . . . . ? C3B N4B C11B C16B 117.7(4) . . . . ? C5B N4B C11B C12B 162.2(3) . . . . ? C3B N4B C11B C12B -64.7(4) . . . . ? C16B C11B C12B C13B 2.3(5) . . . . ? N4B C11B C12B C13B -175.4(3) . . . . ? C16B C11B C12B F1B 179.2(3) . . . . ? N4B C11B C12B F1B 1.4(5) . . . . ? F1B C12B C13B C14B -177.4(3) . . . . ? C11B C12B C13B C14B -0.6(5) . . . . ? C12B C13B C14B C15B -1.7(5) . . . . ? C12B C13B C14B C17B 178.7(3) . . . . ? C13B C14B C15B C16B 2.2(5) . . . . ? C17B C14B C15B C16B -178.2(3) . . . . ? C13B C14B C15B N20B -176.4(3) . . . . ? C17B C14B C15B N20B 3.1(5) . . . . ? N4B C11B C16B C15B 175.9(3) . . . . ? C12B C11B C16B C15B -1.7(5) . . . . ? C14B C15B C16B C11B -0.5(5) . . . . ? N20B C15B C16B C11B 178.2(3) . . . . ? C15B C14B C17B O3B 178.6(3) . . . . ? C13B C14B C17B O3B -1.8(5) . . . . ? C15B C14B C17B C18B -1.5(5) . . . . ? C13B C14B C17B C18B 178.0(3) . . . . ? O3B C17B C18B C19B 178.4(4) . . . . ? C14B C17B C18B C19B -1.5(5) . . . . ? O3B C17B C18B C20B 0.1(5) . . . . ? C14B C17B C18B C20B -179.8(3) . . . . ? C17B C18B C19B N20B 3.1(5) . . . . ? C20B C18B C19B N20B -178.6(3) . . . . ? C18B C19B N20B C15B -1.4(5) . . . . ? C18B C19B N20B C21B -173.8(3) . . . . ? C16B C15B N20B C19B 179.6(3) . . . . ? C14B C15B N20B C19B -1.7(5) . . . . ? C16B C15B N20B C21B -7.8(5) . . . . ? C14B C15B N20B C21B 170.8(3) . . . . ? C19B C18B C20B O1B 0.9(5) . . . . ? C17B C18B C20B O1B 179.3(3) . . . . ? C19B C18B C20B O2B -178.2(3) . . . . ? C17B C18B C20B O2B 0.1(5) . . . . ? C19B N20B C21B C22B -104.5(4) . . . . ? C15B N20B C21B C22B 83.0(4) . . . . ? C19B N20B C21B C23B -32.7(5) . . . . ? C15B N20B C21B C23B 154.8(3) . . . . ? N20B C21B C22B C23B 109.5(4) . . . . ? N20B C21B C23B C22B -109.8(4) . . . . ? C41B P1B C31B C32B -157.4(3) . . . . ? C1B P1B C31B C32B 89.0(4) . . . . ? Se2B P1B C31B C32B -20.6(6) . . . . ? Se1B P1B C31B C32B -32.8(4) . . . . ? C41B P1B C31B C36B 27.4(4) . . . . ? C1B P1B C31B C36B -86.2(3) . . . . ? Se2B P1B C31B C36B 164.2(6) . . . . ? Se1B P1B C31B C36B 152.1(3) . . . . ? C36B C31B C32B C33B 0.3(7) . . . . ? P1B C31B C32B C33B -175.0(4) . . . . ? C31B C32B C33B C34B -1.2(8) . . . . ? C32B C33B C34B C35B 1.1(8) . . . . ? C33B C34B C35B C36B 0.0(8) . . . . ? C34B C35B C36B C31B -0.9(7) . . . . ? C32B C31B C36B C35B 0.8(6) . . . . ? P1B C31B C36B C35B 175.9(3) . . . . ? C31B P1B C41B C42B 109.8(3) . . . . ? C1B P1B C41B C42B -139.4(3) . . . . ? Se2B P1B C41B C42B -7.8(7) . . . . ? Se1B P1B C41B C42B -16.0(3) . . . . ? C31B P1B C41B C46B -74.0(3) . . . . ? C1B P1B C41B C46B 36.8(3) . . . . ? Se2B P1B C41B C46B 168.3(6) . . . . ? Se1B P1B C41B C46B 160.1(2) . . . . ? C46B C41B C42B C43B 0.2(5) . . . . ? P1B C41B C42B C43B 176.5(3) . . . . ? C41B C42B C43B C44B -1.4(5) . . . . ? C42B C43B C44B C45B 1.5(6) . . . . ? C43B C44B C45B C46B -0.4(6) . . . . ? C44B C45B C46B C41B -0.7(5) . . . . ? C42B C41B C46B C45B 0.8(5) . . . . ? P1B C41B C46B C45B -175.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2A H2A1 Se1A 0.99 2.85 3.679(4) 142.2 . C5A H5A2 F12A 0.99 2.19 2.884(4) 125.5 . C6A H6A2 O1B 0.99 2.51 3.496(4) 172.0 2_647 O2A H2A O3A 0.84 1.72 2.501(4) 154.2 . C42A H42A O1B 0.95 2.43 3.193(4) 136.8 2_647 C3B H3B1 F1B 0.99 2.32 2.949(5) 120.9 . C5B H5B1 Se1A 0.99 2.92 3.895(4) 168.7 . C22B H22C O2A 0.99 2.58 3.497(5) 154.5 2_756 C23B H23D O2S 0.99 2.60 3.332(7) 131.2 2_756 O2B H2B O3B 0.84 1.73 2.510(4) 154.4 . C32B H32B Se1B 0.95 2.98 3.479(5) 114.2 . C42B H42B Se1B 0.95 2.86 3.388(4) 116.5 . C46B H46B N1B 0.95 2.52 3.230(5) 132.0 . O1S H1S O2S 0.84 2.14 2.961(9) 166.7 . _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.810 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 948749'