# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_5-OH _database_code_depnum_ccdc_archive 'CCDC 883178' #TrackingRef '5-OH.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H28 N3 O2 P S' _chemical_formula_sum 'C27 H28 N3 O2 P S' _chemical_formula_weight 489.55 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 9.7499(4) _cell_length_b 30.5632(13) _cell_length_c 8.5329(3) _cell_angle_alpha 90 _cell_angle_beta 101.967(2) _cell_angle_gamma 90 _cell_volume 2487.44(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180 _cell_measurement_reflns_used 7578 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.13 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.989 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _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 'Bruker Kappa APEX II' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_unetI/netI 0.0404 _diffrn_reflns_number 33236 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 28.8 _diffrn_reflns_theta_full 28.8 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 6476 _reflns_number_gt 4844 _reflns_threshold_expression >2/sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.7676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6476 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.341 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.07085(4) 0.082245(13) 0.61314(5) 0.02593(11) Uani 1 1 d . . . P1 P 0.75865(4) 0.074117(13) 0.65322(5) 0.02128(10) Uani 1 1 d . . . O1 O 1.59152(14) 0.28877(4) 0.85616(19) 0.0440(4) Uani 1 1 d . . . H1 H 1.628 0.2646 0.8877 0.066 Uiso 1 1 calc R . . O2 O 0.73711(13) 0.21268(4) 0.90661(17) 0.0371(3) Uani 1 1 d . . . N2 N 1.11206(14) 0.14423(4) 0.82592(16) 0.0232(3) Uani 1 1 d . . . N3 N 1.30953(15) 0.12708(5) 0.71784(19) 0.0307(3) Uani 1 1 d . . . N1 N 0.94806(15) 0.22449(4) 0.84164(17) 0.0254(3) Uani 1 1 d . . . H100 H 1.022(2) 0.2123(6) 0.837(2) 0.031 Uiso 1 1 d . . . C12 C 0.93198(16) 0.09695(5) 0.70343(19) 0.0216(3) Uani 1 1 d . . . C9 C 0.85056(17) 0.19921(5) 0.88454(18) 0.0229(3) Uani 1 1 d . . . C22 C 0.73472(16) 0.06967(5) 0.43505(19) 0.0225(3) Uani 1 1 d . . . C8 C 0.93100(18) 0.27121(5) 0.8095(2) 0.0289(4) Uani 1 1 d . . . H8A H 0.8325 0.2795 0.8076 0.035 Uiso 1 1 calc R . . H8B H 0.9503 0.2774 0.7022 0.035 Uiso 1 1 calc R . . C11 C 0.97572(16) 0.13005(5) 0.80975(18) 0.0210(3) Uani 1 1 d . . . C13 C 1.17553(17) 0.12160(5) 0.72932(19) 0.0233(3) Uani 1 1 d . . . C7 C 1.02774(19) 0.29920(5) 0.9337(2) 0.0317(4) Uani 1 1 d . . . H7A H 0.997 0.3301 0.9202 0.038 Uiso 1 1 calc R . . H7B H 1.0191 0.2897 1.0422 0.038 Uiso 1 1 calc R . . C3 C 1.23108(19) 0.32398(6) 0.8169(2) 0.0319(4) Uani 1 1 d . . . H3 H 1.1705 0.3452 0.7577 0.038 Uiso 1 1 calc R . . C2 C 1.3682(2) 0.32131(6) 0.7975(2) 0.0349(4) Uani 1 1 d . . . H2 H 1.4008 0.3407 0.7261 0.042 Uiso 1 1 calc R . . C16 C 0.77639(17) 0.01729(5) 0.72232(18) 0.0227(3) Uani 1 1 d . . . C5 C 1.2719(2) 0.26609(6) 1.0061(2) 0.0332(4) Uani 1 1 d . . . H5 H 1.2398 0.247 1.0787 0.04 Uiso 1 1 calc R . . C1 C 1.45787(18) 0.29033(5) 0.8822(2) 0.0305(4) Uani 1 1 d . . . C23 C 0.70548(17) 0.10868(5) 0.3491(2) 0.0266(4) Uani 1 1 d . . . H23 H 0.6997 0.1353 0.4048 0.032 Uiso 1 1 calc R . . C10 C 0.88594(18) 0.15096(5) 0.91237(19) 0.0253(3) Uani 1 1 d . . . H10A H 0.9338 0.1473 1.0258 0.03 Uiso 1 1 calc R . . H10B H 0.7967 0.1345 0.8969 0.03 Uiso 1 1 calc R . . C27 C 0.74150(18) 0.03092(6) 0.3516(2) 0.0286(4) Uani 1 1 d . . . H27 H 0.7617 0.0042 0.4084 0.034 Uiso 1 1 calc R . . C19 C 0.7790(2) -0.06632(6) 0.8558(2) 0.0325(4) Uani 1 1 d . . . H19 H 0.7801 -0.0944 0.9037 0.039 Uiso 1 1 calc R . . C14 C 1.3984(2) 0.15746(7) 0.8240(3) 0.0424(5) Uani 1 1 d . . . H14A H 1.3423 0.1824 0.8461 0.064 Uiso 1 1 calc R . . H14B H 1.4736 0.1678 0.7728 0.064 Uiso 1 1 calc R . . H14C H 1.4394 0.1426 0.9247 0.064 Uiso 1 1 calc R . . C25 C 0.6903(2) 0.07004(6) 0.1017(2) 0.0353(4) Uani 1 1 d . . . H25 H 0.6745 0.0701 -0.012 0.042 Uiso 1 1 calc R . . C4 C 1.17957(18) 0.29630(5) 0.9208(2) 0.0263(4) Uani 1 1 d . . . C6 C 1.4098(2) 0.26299(6) 0.9885(2) 0.0337(4) Uani 1 1 d . . . H6 H 1.4711 0.2422 1.0491 0.04 Uiso 1 1 calc R . . C17 C 0.9011(2) -0.00312(6) 0.7891(3) 0.0429(5) Uani 1 1 d . . . H17 H 0.9873 0.0114 0.79 0.051 Uiso 1 1 calc R . . C18 C 0.9018(2) -0.04483(6) 0.8551(3) 0.0487(6) Uani 1 1 d . . . H18 H 0.9886 -0.0585 0.9001 0.058 Uiso 1 1 calc R . . C26 C 0.7189(2) 0.03120(6) 0.1855(2) 0.0349(4) Uani 1 1 d . . . H26 H 0.7231 0.0046 0.1291 0.042 Uiso 1 1 calc R . . C24 C 0.68488(18) 0.10882(6) 0.1837(2) 0.0319(4) Uani 1 1 d . . . H24 H 0.667 0.1356 0.1264 0.038 Uiso 1 1 calc R . . C21 C 0.65255(19) -0.00532(6) 0.7213(2) 0.0330(4) Uani 1 1 d . . . H21 H 0.5655 0.008 0.6751 0.04 Uiso 1 1 calc R . . C15 C 1.3721(2) 0.09865(7) 0.6165(3) 0.0418(5) Uani 1 1 d . . . H15A H 1.3969 0.0707 0.671 0.063 Uiso 1 1 calc R . . H15B H 1.4568 0.1125 0.5943 0.063 Uiso 1 1 calc R . . H15C H 1.3051 0.0936 0.5155 0.063 Uiso 1 1 calc R . . C20 C 0.6538(2) -0.04692(6) 0.7866(2) 0.0368(4) Uani 1 1 d . . . H20 H 0.5681 -0.062 0.7835 0.044 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 S1 0.0214(2) 0.0195(2) 0.0383(2) -0.00610(16) 0.00949(17) 0.00018(16) P1 0.0185(2) 0.01662(19) 0.0288(2) 0.00025(15) 0.00511(16) 0.00018(15) O1 0.0290(7) 0.0257(7) 0.0801(10) 0.0018(7) 0.0180(7) 0.0003(6) O2 0.0281(7) 0.0280(7) 0.0603(8) -0.0018(6) 0.0208(6) 0.0011(5) N2 0.0212(7) 0.0197(6) 0.0283(7) 0.0011(5) 0.0040(5) -0.0018(5) N3 0.0183(7) 0.0265(8) 0.0472(9) -0.0022(6) 0.0064(6) -0.0015(6) N1 0.0204(7) 0.0191(7) 0.0385(8) 0.0018(6) 0.0099(6) 0.0006(6) C12 0.0191(8) 0.0177(7) 0.0292(8) 0.0002(6) 0.0075(6) 0.0012(6) C9 0.0233(8) 0.0222(8) 0.0239(7) -0.0041(6) 0.0063(6) -0.0024(6) C22 0.0161(7) 0.0221(8) 0.0294(8) 0.0009(6) 0.0051(6) -0.0002(6) C8 0.0253(9) 0.0197(8) 0.0432(10) 0.0052(7) 0.0106(7) 0.0020(7) C11 0.0225(8) 0.0161(7) 0.0249(7) 0.0027(6) 0.0061(6) 0.0004(6) C13 0.0200(8) 0.0176(8) 0.0315(8) 0.0037(6) 0.0032(6) 0.0010(6) C7 0.0356(10) 0.0198(8) 0.0444(10) -0.0045(7) 0.0190(8) -0.0012(7) C3 0.0303(10) 0.0217(8) 0.0443(10) 0.0061(7) 0.0093(8) 0.0011(7) C2 0.0343(10) 0.0241(9) 0.0494(11) 0.0072(8) 0.0157(8) -0.0027(8) C16 0.0238(8) 0.0192(8) 0.0251(7) -0.0008(6) 0.0049(6) -0.0015(6) C5 0.0386(11) 0.0264(9) 0.0353(9) 0.0032(7) 0.0092(8) -0.0034(8) C1 0.0242(9) 0.0188(8) 0.0494(10) -0.0050(7) 0.0096(8) -0.0021(7) C23 0.0227(8) 0.0209(8) 0.0360(9) 0.0024(6) 0.0056(7) -0.0002(7) C10 0.0303(9) 0.0192(8) 0.0286(8) -0.0016(6) 0.0114(7) -0.0041(7) C27 0.0285(9) 0.0229(8) 0.0349(9) 0.0004(7) 0.0077(7) 0.0030(7) C19 0.0454(11) 0.0202(8) 0.0323(9) 0.0028(7) 0.0088(8) -0.0029(8) C14 0.0264(10) 0.0460(12) 0.0518(12) -0.0001(9) 0.0008(9) -0.0120(9) C25 0.0340(10) 0.0451(11) 0.0290(9) 0.0032(8) 0.0117(7) -0.0020(9) C4 0.0297(9) 0.0173(8) 0.0331(8) -0.0057(6) 0.0092(7) -0.0044(7) C6 0.0331(10) 0.0228(9) 0.0432(10) 0.0018(7) 0.0034(8) 0.0011(7) C17 0.0255(10) 0.0304(10) 0.0688(14) 0.0167(9) 0.0005(9) -0.0033(8) C18 0.0355(11) 0.0316(11) 0.0719(15) 0.0201(10) -0.0049(10) 0.0031(9) C26 0.0375(11) 0.0324(10) 0.0377(10) -0.0088(8) 0.0142(8) 0.0003(8) C24 0.0272(9) 0.0324(10) 0.0370(9) 0.0099(7) 0.0085(7) -0.0008(7) C21 0.0225(9) 0.0238(9) 0.0527(11) 0.0046(8) 0.0080(8) -0.0003(7) C15 0.0255(10) 0.0367(11) 0.0675(14) -0.0014(9) 0.0198(9) 0.0048(8) C20 0.0318(10) 0.0251(9) 0.0563(12) 0.0017(8) 0.0159(9) -0.0064(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C13 1.7470(16) . ? S1 C12 1.7497(16) . ? P1 C12 1.7962(16) . ? P1 C16 1.8308(16) . ? P1 C22 1.8326(16) . ? O1 C1 1.368(2) . ? O1 H1 0.84 . ? O2 C9 1.231(2) . ? N2 C13 1.324(2) . ? N2 C11 1.378(2) . ? N3 C13 1.341(2) . ? N3 C15 1.447(2) . ? N3 C14 1.452(2) . ? N1 C9 1.334(2) . ? N1 C8 1.457(2) . ? N1 H100 0.82(2) . ? C12 C11 1.367(2) . ? C9 C10 1.522(2) . ? C22 C27 1.391(2) . ? C22 C23 1.398(2) . ? C8 C7 1.527(2) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C11 C10 1.503(2) . ? C7 C4 1.509(2) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C3 C2 1.383(3) . ? C3 C4 1.393(2) . ? C3 H3 0.95 . ? C2 C1 1.387(3) . ? C2 H2 0.95 . ? C16 C17 1.380(2) . ? C16 C21 1.390(2) . ? C5 C4 1.386(2) . ? C5 C6 1.387(3) . ? C5 H5 0.95 . ? C1 C6 1.384(3) . ? C23 C24 1.384(2) . ? C23 H23 0.95 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C27 C26 1.389(2) . ? C27 H27 0.95 . ? C19 C18 1.367(3) . ? C19 C20 1.376(3) . ? C19 H19 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C25 C24 1.383(3) . ? C25 C26 1.384(3) . ? C25 H25 0.95 . ? C6 H6 0.95 . ? C17 C18 1.393(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C26 H26 0.95 . ? C24 H24 0.95 . ? C21 C20 1.387(2) . ? C21 H21 0.95 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C20 H20 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 S1 C12 89.29(8) . . ? C12 P1 C16 105.69(7) . . ? C12 P1 C22 100.74(7) . . ? C16 P1 C22 103.91(7) . . ? C1 O1 H1 109.5 . . ? C13 N2 C11 109.84(13) . . ? C13 N3 C15 120.45(15) . . ? C13 N3 C14 119.93(15) . . ? C15 N3 C14 119.05(15) . . ? C9 N1 C8 124.02(15) . . ? C9 N1 H100 115.7(13) . . ? C8 N1 H100 120.2(13) . . ? C11 C12 S1 108.60(12) . . ? C11 C12 P1 126.49(12) . . ? S1 C12 P1 124.81(9) . . ? O2 C9 N1 124.22(15) . . ? O2 C9 C10 118.82(14) . . ? N1 C9 C10 116.93(14) . . ? C27 C22 C23 118.96(15) . . ? C27 C22 P1 125.01(12) . . ? C23 C22 P1 116.02(12) . . ? N1 C8 C7 112.85(14) . . ? N1 C8 H8A 109 . . ? C7 C8 H8A 109 . . ? N1 C8 H8B 109 . . ? C7 C8 H8B 109 . . ? H8A C8 H8B 107.8 . . ? C12 C11 N2 117.46(14) . . ? C12 C11 C10 124.20(14) . . ? N2 C11 C10 118.32(14) . . ? N2 C13 N3 124.67(15) . . ? N2 C13 S1 114.80(12) . . ? N3 C13 S1 120.53(12) . . ? C4 C7 C8 113.00(14) . . ? C4 C7 H7A 109 . . ? C8 C7 H7A 109 . . ? C4 C7 H7B 109 . . ? C8 C7 H7B 109 . . ? H7A C7 H7B 107.8 . . ? C2 C3 C4 121.70(17) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C2 C1 119.90(16) . . ? C3 C2 H2 120 . . ? C1 C2 H2 120 . . ? C17 C16 C21 117.89(15) . . ? C17 C16 P1 125.31(13) . . ? C21 C16 P1 116.48(12) . . ? C4 C5 C6 121.81(16) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? O1 C1 C6 123.29(16) . . ? O1 C1 C2 117.26(16) . . ? C6 C1 C2 119.44(17) . . ? C24 C23 C22 120.55(16) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C11 C10 C9 117.49(13) . . ? C11 C10 H10A 107.9 . . ? C9 C10 H10A 107.9 . . ? C11 C10 H10B 107.9 . . ? C9 C10 H10B 107.9 . . ? H10A C10 H10B 107.2 . . ? C26 C27 C22 120.20(16) . . ? C26 C27 H27 119.9 . . ? C22 C27 H27 119.9 . . ? C18 C19 C20 119.43(16) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C24 C25 C26 119.87(17) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C5 C4 C3 117.29(16) . . ? C5 C4 C7 122.75(16) . . ? C3 C4 C7 119.94(16) . . ? C1 C6 C5 119.82(17) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C16 C17 C18 120.72(18) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.68(18) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C25 C26 C27 120.35(17) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C25 C24 C23 120.05(16) . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? C20 C21 C16 121.22(17) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C19 C20 C21 120.03(17) . . ? C19 C20 H20 120 . . ? C21 C20 H20 120 . . ? data_5-OMe _database_code_depnum_ccdc_archive 'CCDC 883179' #TrackingRef '5-OMe.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H30 N3 O2 P S' _chemical_formula_sum 'C28 H30 N3 O2 P S' _chemical_formula_weight 503.59 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 16.0609(10) _cell_length_b 18.7305(13) _cell_length_c 8.9676(6) _cell_angle_alpha 90 _cell_angle_beta 98.481(6) _cell_angle_gamma 90 _cell_volume 2668.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3213 _cell_measurement_theta_min 3.3548 _cell_measurement_theta_max 29.1195 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.990 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1133 _diffrn_reflns_av_unetI/netI 0.1863 _diffrn_reflns_number 26130 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4883 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0101P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4883 _refine_ls_number_parameters 322 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.121 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0497 _refine_ls_wR_factor_gt 0.0432 _refine_ls_goodness_of_fit_ref 0.664 _refine_ls_restrained_S_all 0.664 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.22 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.57946(16) 0.22064(15) 0.6983(3) 0.0612(9) Uani 1 1 d . . . H1A H -0.5941 0.2231 0.8005 0.092 Uiso 1 1 calc R . . H1B H -0.6302 0.2107 0.6264 0.092 Uiso 1 1 calc R . . H1C H -0.5553 0.2663 0.6731 0.092 Uiso 1 1 calc R . . C2 C -0.44009(18) 0.17526(15) 0.7673(3) 0.0360(7) Uani 1 1 d . . . C3 C -0.37961(18) 0.12621(14) 0.7415(2) 0.0395(7) Uani 1 1 d . . . H3 H -0.3948 0.0874 0.6749 0.047 Uiso 1 1 calc R . . C4 C -0.29819(17) 0.13271(14) 0.8103(3) 0.0392(7) Uani 1 1 d . . . H4 H -0.2577 0.0987 0.7888 0.047 Uiso 1 1 calc R . . C5 C -0.27292(17) 0.18773(15) 0.9109(3) 0.0376(7) Uani 1 1 d . . . C6 C -0.33448(18) 0.23481(15) 0.9393(3) 0.0499(8) Uani 1 1 d . . . H6 H -0.3198 0.272 1.0104 0.06 Uiso 1 1 calc R . . C7 C -0.41733(17) 0.23011(15) 0.8682(3) 0.0490(8) Uani 1 1 d . . . H7 H -0.4579 0.2643 0.8888 0.059 Uiso 1 1 calc R . . C8 C -0.18331(16) 0.19445(15) 0.9847(3) 0.0457(8) Uani 1 1 d . . . H8A H -0.1519 0.1515 0.9609 0.055 Uiso 1 1 calc R . . H8B H -0.1819 0.1961 1.0954 0.055 Uiso 1 1 calc R . . C9 C -0.13977(17) 0.25938(15) 0.9363(3) 0.0567(8) Uani 1 1 d . . . H9A H -0.1447 0.2594 0.8249 0.068 Uiso 1 1 calc R . . H9B H -0.169 0.3024 0.9663 0.068 Uiso 1 1 calc R . . C10 C 0.00954(19) 0.23570(13) 0.9307(3) 0.0367(7) Uani 1 1 d . . . C11 C 0.09661(15) 0.23152(13) 1.0244(3) 0.0360(7) Uani 1 1 d . . . H11A H 0.1402 0.2469 0.9639 0.043 Uiso 1 1 calc R . . H11B H 0.0996 0.2628 1.1141 0.043 Uiso 1 1 calc R . . C12 C 0.11005(15) 0.15497(13) 1.0717(2) 0.0290(6) Uani 1 1 d . . . C13 C 0.06442(14) 0.06000(14) 1.1800(2) 0.0276(6) Uani 1 1 d . . . C14 C 0.02586(15) -0.05813(13) 1.2579(2) 0.0390(7) Uani 1 1 d . . . H14A H 0.0127 -0.0746 1.1534 0.059 Uiso 1 1 calc R . . H14B H -0.014 -0.0793 1.3181 0.059 Uiso 1 1 calc R . . H14C H 0.0832 -0.0726 1.2994 0.059 Uiso 1 1 calc R . . C15 C -0.05490(15) 0.05074(12) 1.3111(2) 0.0404(7) Uani 1 1 d . . . H15A H -0.0427 0.1003 1.3421 0.061 Uiso 1 1 calc R . . H15B H -0.0702 0.0235 1.3964 0.061 Uiso 1 1 calc R . . H15C H -0.1018 0.0497 1.2276 0.061 Uiso 1 1 calc R . . C16 C 0.16778(15) 0.10873(12) 1.0309(2) 0.0289(6) Uani 1 1 d . . . C17 C 0.34585(15) 0.10495(12) 1.0766(3) 0.0312(7) Uani 1 1 d . . . C18 C 0.34210(16) 0.10605(13) 1.2314(3) 0.0422(8) Uani 1 1 d . . . H18 H 0.2905 0.1173 1.2659 0.051 Uiso 1 1 calc R . . C19 C 0.4132(2) 0.09076(15) 1.3355(3) 0.0539(9) Uani 1 1 d . . . H19 H 0.4098 0.091 1.4404 0.065 Uiso 1 1 calc R . . C20 C 0.48845(19) 0.07528(14) 1.2860(3) 0.0575(9) Uani 1 1 d . . . H20 H 0.5368 0.0645 1.3569 0.069 Uiso 1 1 calc R . . C21 C 0.49365(17) 0.07538(14) 1.1345(3) 0.0508(8) Uani 1 1 d . . . H21 H 0.5457 0.0653 1.1007 0.061 Uiso 1 1 calc R . . C22 C 0.42342(17) 0.09010(13) 1.0318(3) 0.0392(7) Uani 1 1 d . . . H22 H 0.4279 0.0901 0.9273 0.047 Uiso 1 1 calc R . . C23 C 0.25690(15) 0.05857(15) 0.7990(3) 0.0318(7) Uani 1 1 d . . . C24 C 0.28055(14) -0.01127(15) 0.8371(3) 0.0341(7) Uani 1 1 d . . . H24 H 0.2969 -0.0232 0.9402 0.041 Uiso 1 1 calc R . . C25 C 0.28085(14) -0.06405(15) 0.7283(3) 0.0440(8) Uani 1 1 d . . . H25 H 0.2963 -0.1116 0.7567 0.053 Uiso 1 1 calc R . . C26 C 0.25845(17) -0.04643(19) 0.5787(4) 0.0571(9) Uani 1 1 d . . . H26 H 0.2598 -0.0819 0.5033 0.069 Uiso 1 1 calc R . . C27 C 0.23420(18) 0.0219(2) 0.5375(3) 0.0559(9) Uani 1 1 d . . . H27 H 0.2177 0.0331 0.434 0.067 Uiso 1 1 calc R . . C28 C 0.23362(15) 0.07532(15) 0.6470(3) 0.0465(8) Uani 1 1 d . . . H28 H 0.2175 0.1227 0.6177 0.056 Uiso 1 1 calc R . . N1 N -0.05131(14) 0.26403(11) 0.9994(2) 0.0353(6) Uani 1 1 d D . . H101 H -0.0394(13) 0.2722(11) 1.0949(11) 0.042 Uiso 1 1 d D . . N2 N 0.05176(11) 0.12805(11) 1.15536(19) 0.0300(5) Uani 1 1 d . . . N3 N 0.01941(12) 0.01904(12) 1.26222(19) 0.0322(5) Uani 1 1 d . . . O1 O -0.51913(12) 0.16478(9) 0.69112(18) 0.0496(5) Uani 1 1 d . . . O2 O -0.00336(12) 0.21143(9) 0.80257(17) 0.0615(6) Uani 1 1 d . . . P1 P 0.25615(4) 0.13102(4) 0.93642(7) 0.0349(2) Uani 1 1 d . . . S1 S 0.14850(4) 0.02386(3) 1.09921(6) 0.03116(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 C1 0.0345(19) 0.059(2) 0.088(2) 0.0120(18) 0.0007(16) 0.0030(18) C2 0.0353(19) 0.040(2) 0.0322(17) 0.0064(15) 0.0022(15) 0.0012(17) C3 0.050(2) 0.0298(18) 0.0367(17) -0.0041(13) -0.0013(15) 0.0065(17) C4 0.042(2) 0.039(2) 0.0367(17) 0.0010(15) 0.0043(14) 0.0162(17) C5 0.040(2) 0.046(2) 0.0255(17) 0.0052(14) 0.0025(14) 0.0051(17) C6 0.049(2) 0.055(2) 0.0447(19) -0.0218(15) 0.0049(16) -0.0015(19) C7 0.039(2) 0.052(2) 0.057(2) -0.0153(17) 0.0138(17) 0.0089(17) C8 0.044(2) 0.053(2) 0.0363(17) 0.0064(14) -0.0049(14) 0.0040(17) C9 0.045(2) 0.056(2) 0.060(2) 0.0076(16) -0.0233(16) -0.0006(19) C10 0.068(2) 0.0127(17) 0.0303(18) 0.0073(13) 0.0100(17) -0.0001(16) C11 0.0420(19) 0.0270(19) 0.0441(17) -0.0018(13) 0.0231(15) -0.0056(15) C12 0.0260(16) 0.0254(18) 0.0362(16) 0.0022(13) 0.0067(13) -0.0055(14) C13 0.0257(16) 0.0261(18) 0.0316(16) 0.0040(13) 0.0062(12) -0.0031(14) C14 0.049(2) 0.0304(19) 0.0386(17) 0.0060(14) 0.0103(13) -0.0038(16) C15 0.0426(19) 0.037(2) 0.0453(18) 0.0036(13) 0.0195(14) 0.0022(15) C16 0.0288(16) 0.0246(17) 0.0355(16) -0.0010(12) 0.0119(13) -0.0043(14) C17 0.0271(17) 0.0301(18) 0.0370(17) -0.0075(13) 0.0063(13) -0.0070(14) C18 0.0315(18) 0.054(2) 0.0419(19) -0.0076(14) 0.0085(15) -0.0093(16) C19 0.055(2) 0.069(2) 0.0372(19) -0.0076(15) 0.0029(18) -0.0193(19) C20 0.042(2) 0.062(2) 0.062(2) -0.0073(18) -0.0173(17) -0.0041(18) C21 0.0273(19) 0.064(2) 0.059(2) -0.0188(17) -0.0001(17) -0.0025(17) C22 0.0337(18) 0.044(2) 0.0393(18) -0.0115(14) 0.0048(15) -0.0039(16) C23 0.0258(16) 0.044(2) 0.0273(18) 0.0018(14) 0.0091(12) -0.0057(15) C24 0.0236(16) 0.048(2) 0.0311(16) -0.0063(16) 0.0061(12) 0.0011(15) C25 0.0317(18) 0.052(2) 0.049(2) -0.0134(17) 0.0080(15) -0.0013(15) C26 0.043(2) 0.082(3) 0.051(2) -0.0292(19) 0.0225(17) -0.023(2) C27 0.049(2) 0.094(3) 0.0252(19) 0.000(2) 0.0053(14) -0.032(2) C28 0.0356(18) 0.062(2) 0.041(2) 0.0092(18) 0.0049(15) -0.0131(16) N1 0.0407(15) 0.0357(15) 0.0261(13) -0.0019(12) -0.0065(13) 0.0053(13) N2 0.0291(13) 0.0225(14) 0.0413(13) 0.0059(11) 0.0145(11) -0.0002(11) N3 0.0317(14) 0.0248(14) 0.0427(13) 0.0030(12) 0.0146(11) -0.0004(13) O1 0.0351(13) 0.0521(14) 0.0589(13) 0.0005(10) -0.0012(10) 0.0027(11) O2 0.1338(19) 0.0309(13) 0.0198(11) -0.0055(9) 0.0114(11) 0.0013(13) P1 0.0308(5) 0.0346(5) 0.0419(4) 0.0018(4) 0.0140(3) -0.0017(4) S1 0.0282(4) 0.0270(4) 0.0396(4) 0.0034(3) 0.0095(3) 0.0048(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.434(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O1 1.364(3) . ? C2 C3 1.381(3) . ? C2 C7 1.382(3) . ? C3 C4 1.367(3) . ? C3 H3 0.95 . ? C4 C5 1.390(3) . ? C4 H4 0.95 . ? C5 C6 1.376(3) . ? C5 C8 1.498(3) . ? C6 C7 1.391(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C9 1.499(3) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 N1 1.452(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 O2 1.224(2) . ? C10 N1 1.340(3) . ? C10 C11 1.524(3) . ? C11 C12 1.502(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C16 1.358(3) . ? C12 N2 1.379(3) . ? C13 N2 1.304(3) . ? C13 N3 1.346(3) . ? C13 S1 1.759(2) . ? C14 N3 1.450(2) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 N3 1.457(3) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 S1 1.748(2) . ? C16 P1 1.806(2) . ? C17 C22 1.392(3) . ? C17 C18 1.398(3) . ? C17 P1 1.833(2) . ? C18 C19 1.394(3) . ? C18 H18 0.95 . ? C19 C20 1.378(3) . ? C19 H19 0.95 . ? C20 C21 1.373(3) . ? C20 H20 0.95 . ? C21 C22 1.375(3) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 C24 1.391(3) . ? C23 C28 1.396(3) . ? C23 P1 1.834(3) . ? C24 C25 1.390(3) . ? C24 H24 0.95 . ? C25 C26 1.377(3) . ? C25 H25 0.95 . ? C26 C27 1.372(3) . ? C26 H26 0.95 . ? C27 C28 1.403(3) . ? C27 H27 0.95 . ? C28 H28 0.95 . ? N1 H101 0.863(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 O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 116.5(2) . . ? O1 C2 C7 124.9(3) . . ? C3 C2 C7 118.7(2) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.8(2) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 116.5(2) . . ? C6 C5 C8 122.3(3) . . ? C4 C5 C8 121.2(3) . . ? C5 C6 C7 122.6(2) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C2 C7 C6 119.3(2) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C5 C8 C9 113.5(2) . . ? C5 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C5 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N1 C9 C8 114.0(2) . . ? N1 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? N1 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? O2 C10 N1 123.0(3) . . ? O2 C10 C11 120.9(3) . . ? N1 C10 C11 116.0(2) . . ? C12 C11 C10 106.7(2) . . ? C12 C11 H11A 110.4 . . ? C10 C11 H11A 110.4 . . ? C12 C11 H11B 110.4 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C16 C12 N2 117.3(2) . . ? C16 C12 C11 127.5(2) . . ? N2 C12 C11 114.9(2) . . ? N2 C13 N3 124.5(2) . . ? N2 C13 S1 114.60(18) . . ? N3 C13 S1 120.86(19) . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 S1 108.81(17) . . ? C12 C16 P1 126.45(18) . . ? S1 C16 P1 124.54(14) . . ? C22 C17 C18 117.4(2) . . ? C22 C17 P1 120.09(19) . . ? C18 C17 P1 122.16(19) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 120.2(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.0(3) . . ? C20 C21 H21 120 . . ? C22 C21 H21 120 . . ? C21 C22 C17 121.8(2) . . ? C21 C22 H22 119.1 . . ? C17 C22 H22 119.1 . . ? C24 C23 C28 118.4(2) . . ? C24 C23 P1 124.04(19) . . ? C28 C23 P1 117.6(2) . . ? C25 C24 C23 121.7(2) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C26 C25 C24 119.1(3) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C27 C26 C25 120.6(3) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 120.5(3) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C23 C28 C27 119.7(3) . . ? C23 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C10 N1 C9 122.3(2) . . ? C10 N1 H101 117.2(15) . . ? C9 N1 H101 117.3(15) . . ? C13 N2 C12 110.4(2) . . ? C13 N3 C14 120.5(2) . . ? C13 N3 C15 117.5(2) . . ? C14 N3 C15 118.6(2) . . ? C2 O1 C1 117.2(2) . . ? C16 P1 C17 102.08(11) . . ? C16 P1 C23 103.14(11) . . ? C17 P1 C23 100.44(12) . . ? C16 S1 C13 88.90(12) . . ? data_3 _database_code_depnum_ccdc_archive 'CCDC 883180' #TrackingRef 'compound 3.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H23 N2 O2 P S' _chemical_formula_sum 'C21 H23 N2 O2 P S' _chemical_formula_weight 398.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7642(9) _cell_length_b 10.8437(11) _cell_length_c 12.1558(12) _cell_angle_alpha 94.396(5) _cell_angle_beta 106.808(5) _cell_angle_gamma 109.396(5) _cell_volume 1023.87(19) _cell_formula_units_Z 2 _cell_measurement_temperature 180 _cell_measurement_reflns_used 9892 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.125 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.979 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_unetI/netI 0.0122 _diffrn_reflns_number 20382 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3739 _reflns_number_gt 3487 _reflns_threshold_expression >2/sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.6584P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3739 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.714 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.44807(5) 0.04626(4) 0.19529(3) 0.02555(11) Uani 1 1 d . . . P1 P 0.52208(5) 0.32265(4) 0.34987(3) 0.02342(11) Uani 1 1 d . . . O2 O 0.86844(15) 0.45442(12) 0.20103(11) 0.0377(3) Uani 1 1 d . . . O1 O 1.12114(15) 0.52306(13) 0.34868(11) 0.0404(3) Uani 1 1 d . . . N1 N 0.77431(16) 0.12059(13) 0.23215(11) 0.0257(3) Uani 1 1 d . . . N2 N 0.6109(2) -0.08567(14) 0.10462(13) 0.0352(3) Uani 1 1 d . . . C10 C 0.3564(2) 0.33352(15) 0.22210(13) 0.0238(3) Uani 1 1 d . . . C5 C 0.74816(19) 0.21870(15) 0.29393(13) 0.0226(3) Uani 1 1 d . . . C4 C 0.90294(19) 0.33847(15) 0.36342(13) 0.0270(3) Uani 1 1 d . . . H4A H 0.9977 0.3102 0.3967 0.032 Uiso 1 1 calc R . . H4B H 0.8791 0.3779 0.4278 0.032 Uiso 1 1 calc R . . C16 C 0.3983(2) 0.24041(16) 0.43957(13) 0.0255(3) Uani 1 1 d . . . C11 C 0.4133(2) 0.42008(16) 0.15059(15) 0.0314(4) Uani 1 1 d . . . H11 H 0.5301 0.4682 0.1692 0.038 Uiso 1 1 calc R . . C7 C 0.6272(2) 0.02334(15) 0.17512(13) 0.0254(3) Uani 1 1 d . . . C15 C 0.1815(2) 0.26376(17) 0.19357(14) 0.0315(4) Uani 1 1 d . . . H15 H 0.1413 0.2056 0.2401 0.038 Uiso 1 1 calc R . . C6 C 0.58407(19) 0.19935(14) 0.28767(13) 0.0223(3) Uani 1 1 d . . . C3 C 0.9566(2) 0.44296(16) 0.29282(14) 0.0279(3) Uani 1 1 d . . . C21 C 0.3366(2) 0.31808(17) 0.49864(14) 0.0308(4) Uani 1 1 d . . . H21 H 0.3529 0.4045 0.4866 0.037 Uiso 1 1 calc R . . C9 C 0.4479(3) -0.19567(18) 0.05483(18) 0.0458(5) Uani 1 1 d . . . H9A H 0.4321 -0.2522 0.1109 0.069 Uiso 1 1 calc R . . H9B H 0.4464 -0.2459 -0.0143 0.069 Uiso 1 1 calc R . . H9C H 0.357 -0.162 0.0348 0.069 Uiso 1 1 calc R . . C20 C 0.2517(2) 0.2680(2) 0.57491(15) 0.0381(4) Uani 1 1 d . . . H20 H 0.2113 0.3209 0.6136 0.046 Uiso 1 1 calc R . . C12 C 0.2975(3) 0.43504(17) 0.05219(15) 0.0382(4) Uani 1 1 d . . . H12 H 0.3369 0.4916 0.0043 0.046 Uiso 1 1 calc R . . C13 C 0.1247(3) 0.3661(2) 0.02564(15) 0.0405(4) Uani 1 1 d . . . H13 H 0.0467 0.377 -0.0396 0.049 Uiso 1 1 calc R . . C19 C 0.2266(3) 0.1398(2) 0.59387(16) 0.0431(5) Uani 1 1 d . . . H19 H 0.1676 0.1055 0.6439 0.052 Uiso 1 1 calc R . . C18 C 0.2901(3) 0.0633(2) 0.53780(17) 0.0452(5) Uani 1 1 d . . . H18 H 0.2754 -0.0224 0.5514 0.054 Uiso 1 1 calc R . . C17 C 0.3755(2) 0.11293(18) 0.46130(15) 0.0359(4) Uani 1 1 d . . . H17 H 0.4179 0.0602 0.4243 0.043 Uiso 1 1 calc R . . C14 C 0.0665(2) 0.2805(2) 0.09596(16) 0.0409(4) Uani 1 1 d . . . H14 H -0.0506 0.2338 0.0776 0.049 Uiso 1 1 calc R . . C8 C 0.7637(3) -0.1063(2) 0.09719(17) 0.0473(5) Uani 1 1 d . . . H8A H 0.8599 -0.0231 0.1244 0.071 Uiso 1 1 calc R . . H8B H 0.7458 -0.1403 0.0173 0.071 Uiso 1 1 calc R . . H8C H 0.7862 -0.169 0.145 0.071 Uiso 1 1 calc R . . C2 C 1.1970(2) 0.6287(2) 0.29065(18) 0.0455(5) Uani 1 1 d . . . H2A H 1.321 0.6559 0.3191 0.055 Uiso 1 1 calc R . . H2B H 1.1563 0.5957 0.2069 0.055 Uiso 1 1 calc R . . C1 C 1.1502(4) 0.7428(2) 0.3142(2) 0.0744(8) Uani 1 1 d . . . H1A H 1.0287 0.7182 0.2783 0.112 Uiso 1 1 calc R . . H1B H 1.2097 0.815 0.2827 0.112 Uiso 1 1 calc R . . H1C H 1.1815 0.7703 0.3972 0.112 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 S1 0.0247(2) 0.0223(2) 0.0278(2) 0.00092(15) 0.01081(16) 0.00547(15) P1 0.0253(2) 0.0218(2) 0.0240(2) 0.00235(15) 0.00845(16) 0.01012(16) O2 0.0297(6) 0.0392(7) 0.0344(7) 0.0146(5) 0.0030(5) 0.0058(5) O1 0.0293(6) 0.0400(7) 0.0337(7) 0.0092(5) 0.0021(5) -0.0032(5) N1 0.0280(7) 0.0291(7) 0.0255(7) 0.0071(5) 0.0124(5) 0.0141(6) N2 0.0450(9) 0.0304(7) 0.0343(8) -0.0008(6) 0.0162(7) 0.0179(7) C10 0.0297(8) 0.0234(7) 0.0237(7) 0.0038(6) 0.0115(6) 0.0145(6) C5 0.0256(7) 0.0230(7) 0.0212(7) 0.0074(6) 0.0091(6) 0.0099(6) C4 0.0225(7) 0.0299(8) 0.0247(8) 0.0054(6) 0.0052(6) 0.0072(6) C16 0.0267(8) 0.0318(8) 0.0189(7) 0.0043(6) 0.0057(6) 0.0136(7) C11 0.0397(9) 0.0254(8) 0.0313(9) 0.0067(7) 0.0154(7) 0.0113(7) C7 0.0329(8) 0.0261(8) 0.0233(8) 0.0079(6) 0.0137(7) 0.0141(7) C15 0.0307(8) 0.0404(9) 0.0279(8) 0.0103(7) 0.0141(7) 0.0141(7) C6 0.0240(7) 0.0206(7) 0.0220(7) 0.0035(6) 0.0082(6) 0.0076(6) C3 0.0242(8) 0.0275(8) 0.0273(8) 0.0025(6) 0.0067(7) 0.0057(6) C21 0.0330(9) 0.0365(9) 0.0275(8) 0.0048(7) 0.0097(7) 0.0191(7) C9 0.0620(13) 0.0278(9) 0.0432(11) -0.0020(8) 0.0213(10) 0.0100(9) C20 0.0410(10) 0.0562(11) 0.0289(9) 0.0088(8) 0.0160(8) 0.0289(9) C12 0.0620(12) 0.0314(9) 0.0306(9) 0.0122(7) 0.0206(9) 0.0232(9) C13 0.0533(11) 0.0550(12) 0.0257(9) 0.0104(8) 0.0104(8) 0.0375(10) C19 0.0510(11) 0.0616(13) 0.0310(9) 0.0201(9) 0.0236(9) 0.0278(10) C18 0.0674(13) 0.0437(11) 0.0404(10) 0.0218(9) 0.0296(10) 0.0274(10) C17 0.0539(11) 0.0367(9) 0.0307(9) 0.0121(7) 0.0224(8) 0.0254(8) C14 0.0308(9) 0.0626(12) 0.0325(9) 0.0077(9) 0.0098(7) 0.0223(9) C8 0.0621(13) 0.0580(12) 0.0375(10) 0.0021(9) 0.0192(9) 0.0408(11) C2 0.0360(10) 0.0457(11) 0.0403(10) 0.0071(9) 0.0100(8) -0.0002(8) C1 0.100(2) 0.0469(13) 0.0741(17) 0.0069(12) 0.0478(16) 0.0092(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.7488(16) . ? S1 C6 1.7503(15) . ? P1 C6 1.7943(15) . ? P1 C16 1.8308(16) . ? P1 C10 1.8362(16) . ? O2 C3 1.201(2) . ? O1 C3 1.3441(19) . ? O1 C2 1.464(2) . ? N1 C7 1.313(2) . ? N1 C5 1.3738(19) . ? N2 C7 1.347(2) . ? N2 C9 1.445(2) . ? N2 C8 1.455(2) . ? C10 C15 1.388(2) . ? C10 C11 1.396(2) . ? C5 C6 1.361(2) . ? C5 C4 1.496(2) . ? C4 C3 1.507(2) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C16 C17 1.387(2) . ? C16 C21 1.397(2) . ? C11 C12 1.387(3) . ? C11 H11 0.93 . ? C15 C14 1.385(2) . ? C15 H15 0.93 . ? C21 C20 1.384(2) . ? C21 H21 0.93 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C20 C19 1.382(3) . ? C20 H20 0.93 . ? C12 C13 1.373(3) . ? C12 H12 0.93 . ? C13 C14 1.383(3) . ? C13 H13 0.93 . ? C19 C18 1.378(3) . ? C19 H19 0.93 . ? C18 C17 1.388(3) . ? C18 H18 0.93 . ? C17 H17 0.93 . ? C14 H14 0.93 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C2 C1 1.460(3) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? 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 C7 S1 C6 89.19(7) . . ? C6 P1 C16 105.74(7) . . ? C6 P1 C10 101.62(7) . . ? C16 P1 C10 103.01(7) . . ? C3 O1 C2 116.76(13) . . ? C7 N1 C5 110.12(13) . . ? C7 N2 C9 121.04(15) . . ? C7 N2 C8 119.69(15) . . ? C9 N2 C8 118.06(15) . . ? C15 C10 C11 118.70(15) . . ? C15 C10 P1 124.68(12) . . ? C11 C10 P1 116.62(12) . . ? C6 C5 N1 117.63(13) . . ? C6 C5 C4 125.09(14) . . ? N1 C5 C4 117.29(13) . . ? C5 C4 C3 113.67(13) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C17 C16 C21 118.26(15) . . ? C17 C16 P1 125.08(12) . . ? C21 C16 P1 116.37(12) . . ? C12 C11 C10 120.74(16) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? N1 C7 N2 123.98(15) . . ? N1 C7 S1 114.68(11) . . ? N2 C7 S1 121.33(13) . . ? C14 C15 C10 120.24(16) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C5 C6 S1 108.38(11) . . ? C5 C6 P1 124.03(11) . . ? S1 C6 P1 127.13(9) . . ? O2 C3 O1 124.54(15) . . ? O2 C3 C4 126.29(14) . . ? O1 C3 C4 109.17(13) . . ? C20 C21 C16 120.82(16) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C19 C20 C21 120.33(16) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C13 C12 C11 119.87(16) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.01(16) . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C18 C19 C20 119.28(17) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C19 C18 C17 120.70(18) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C16 C17 C18 120.58(16) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C14 C15 120.44(17) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 C2 O1 109.93(18) . . ? C1 C2 H2A 109.7 . . ? O1 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? O1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? #===END