# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Christopher Moody' 'Alexander Blake' 'Ian B Campbell' 'Brian D. Judkins' 'Baolu Shi' _publ_contact_author_name 'Christopher Moody' _publ_contact_author_email C.J.MOODY@NOTTINGHAM.AC.UK _publ_section_title ; The rhodium carbene route to oxazoles: a remarkable catalyst effect ; # Attachment 'Cpd_4b.CIF' data_ansomc _database_code_depnum_ccdc_archive 'CCDC 721492' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O4' _chemical_formula_sum 'C13 H13 N O4' _chemical_formula_weight 247.24 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8926(8) _cell_length_b 7.4333(9) _cell_length_c 12.285(2) _cell_angle_alpha 78.908(2) _cell_angle_beta 85.615(2) _cell_angle_gamma 72.613(2) _cell_volume 589.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1703 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.2 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.104 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5217 _diffrn_reflns_av_R_equivalents 0.106 _diffrn_reflns_av_sigmaI/netI 0.084 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2643 _reflns_number_gt 2270 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; ; _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^)+(0.069P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'sp2-bound Me H atoms from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2643 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.132 _refine_ls_wR_factor_gt 0.128 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.001 _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 O1 O 0.28836(12) 0.83193(10) 0.44103(7) 0.0239(2) Uani 1 1 d . . . C2 C 0.49577(17) 0.79490(15) 0.44710(10) 0.0207(3) Uani 1 1 d . . . N3 N 0.57742(14) 0.86896(12) 0.35866(9) 0.0228(2) Uani 1 1 d . . . C4 C 0.41484(18) 0.96269(15) 0.28772(10) 0.0234(3) Uani 1 1 d . . . C5 C 0.23953(18) 0.93973(15) 0.33773(10) 0.0240(3) Uani 1 1 d . . . C6 C 0.59199(17) 0.68401(14) 0.54987(10) 0.0207(3) Uani 1 1 d . . . C7 C 0.48329(18) 0.60803(15) 0.63770(10) 0.0240(3) Uani 1 1 d . . . H7 H 0.3423 0.6258 0.6303 0.029 Uiso 1 1 calc R . . C8 C 0.57749(18) 0.50743(15) 0.73524(10) 0.0254(3) Uani 1 1 d . . . H8 H 0.5015 0.4562 0.7945 0.031 Uiso 1 1 calc R . . C9 C 0.78472(18) 0.48081(15) 0.74695(10) 0.0230(3) Uani 1 1 d . . . C10 C 0.89526(18) 0.55198(15) 0.65930(10) 0.0248(3) Uani 1 1 d . . . H10 H 1.0370 0.5310 0.6662 0.030 Uiso 1 1 calc R . . C11 C 0.79971(18) 0.65389(16) 0.56143(10) 0.0230(3) Uani 1 1 d . . . H11 H 0.8762 0.7035 0.5019 0.028 Uiso 1 1 calc R . . O12 O 0.86362(14) 0.38277(12) 0.84689(7) 0.0312(3) Uani 1 1 d . . . C13 C 1.0678(2) 0.37604(19) 0.86712(12) 0.0362(3) Uani 1 1 d . . . H13A H 1.1075 0.3013 0.9410 0.054 Uiso 1 1 calc R . . H13B H 1.0760 0.5065 0.8632 0.054 Uiso 1 1 calc R . . H13C H 1.1598 0.3157 0.8110 0.054 Uiso 1 1 calc R . . C14 C 0.4359(2) 1.07506(15) 0.17778(10) 0.0264(3) Uani 1 1 d . . . O15 O 0.29674(16) 1.15575(13) 0.11516(9) 0.0390(3) Uani 1 1 d . . . O16 O 0.62802(14) 1.07769(12) 0.15520(8) 0.0325(3) Uani 1 1 d . . . C17 C 0.6649(3) 1.1878(2) 0.05008(12) 0.0421(4) Uani 1 1 d . . . H17A H 0.8095 1.1805 0.0423 0.063 Uiso 1 1 calc R . . H17B H 0.5835 1.3217 0.0463 0.063 Uiso 1 1 calc R . . H17C H 0.6268 1.1362 -0.0100 0.063 Uiso 1 1 calc R . . C18 C 0.02304(19) 1.00213(17) 0.30781(13) 0.0337(3) Uani 1 1 d . . . H18A H 0.0038 1.0948 0.2382 0.050 Uiso 1 1 calc R . . H18B H -0.0600 1.0621 0.3668 0.050 Uiso 1 1 calc R . . H18C H -0.0184 0.8909 0.2986 0.050 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 O1 0.0174(4) 0.0290(4) 0.0235(5) -0.0018(3) -0.0051(3) -0.0049(3) C2 0.0171(5) 0.0228(5) 0.0214(6) -0.0038(4) -0.0038(4) -0.0038(4) N3 0.0214(5) 0.0255(5) 0.0202(5) -0.0024(4) -0.0062(4) -0.0045(4) C4 0.0237(6) 0.0238(5) 0.0213(6) -0.0030(4) -0.0075(5) -0.0036(4) C5 0.0238(6) 0.0233(5) 0.0233(6) -0.0029(4) -0.0091(5) -0.0034(4) C6 0.0215(6) 0.0224(5) 0.0177(6) -0.0038(4) -0.0027(5) -0.0050(4) C7 0.0184(5) 0.0276(6) 0.0249(7) -0.0031(4) -0.0014(5) -0.0056(4) C8 0.0247(6) 0.0298(6) 0.0204(6) -0.0004(4) 0.0022(5) -0.0091(5) C9 0.0258(6) 0.0228(5) 0.0181(6) -0.0010(4) -0.0048(5) -0.0042(4) C10 0.0197(5) 0.0308(6) 0.0226(6) -0.0016(4) -0.0045(5) -0.0065(4) C11 0.0206(6) 0.0284(5) 0.0188(6) -0.0003(4) -0.0013(5) -0.0076(4) O12 0.0309(5) 0.0377(5) 0.0197(5) 0.0054(4) -0.0073(4) -0.0070(4) C13 0.0330(7) 0.0451(7) 0.0256(7) 0.0019(5) -0.0144(6) -0.0056(6) C14 0.0318(7) 0.0253(6) 0.0216(6) -0.0047(4) -0.0078(5) -0.0055(5) O15 0.0419(6) 0.0430(5) 0.0281(5) 0.0028(4) -0.0189(4) -0.0073(4) O16 0.0345(5) 0.0380(5) 0.0215(5) 0.0039(4) -0.0026(4) -0.0107(4) C17 0.0571(10) 0.0472(8) 0.0224(7) 0.0036(6) 0.0000(7) -0.0220(7) C18 0.0228(6) 0.0348(6) 0.0404(8) -0.0016(5) -0.0126(6) -0.0041(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.3707(14) . ? O1 C2 1.3778(13) . ? C2 N3 1.2891(16) . ? C2 C6 1.4540(16) . ? N3 C4 1.3963(14) . ? C4 C5 1.3550(18) . ? C4 C14 1.4668(17) . ? C5 C18 1.4770(16) . ? C6 C7 1.3926(17) . ? C6 C11 1.3955(15) . ? C7 C8 1.3787(16) . ? C7 H7 0.9500 . ? C8 C9 1.3970(16) . ? C8 H8 0.9500 . ? C9 O12 1.3621(13) . ? C9 C10 1.3842(17) . ? C10 C11 1.3876(15) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? O12 C13 1.4326(15) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O15 1.2096(15) . ? C14 O16 1.3371(16) . ? O16 C17 1.4387(16) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C5 O1 C2 104.98(9) . . ? N3 C2 O1 113.59(10) . . ? N3 C2 C6 128.88(11) . . ? O1 C2 C6 117.52(10) . . ? C2 N3 C4 104.48(10) . . ? C5 C4 N3 109.91(11) . . ? C5 C4 C14 126.50(11) . . ? N3 C4 C14 123.54(12) . . ? C4 C5 O1 107.03(10) . . ? C4 C5 C18 135.91(12) . . ? O1 C5 C18 117.05(11) . . ? C7 C6 C11 118.80(11) . . ? C7 C6 C2 122.15(10) . . ? C11 C6 C2 119.04(11) . . ? C8 C7 C6 120.91(11) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.96(11) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? O12 C9 C10 124.60(11) . . ? O12 C9 C8 115.78(11) . . ? C10 C9 C8 119.62(11) . . ? C9 C10 C11 120.22(11) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 120.45(11) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C9 O12 C13 117.08(10) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O15 C14 O16 124.06(12) . . ? O15 C14 C4 124.24(13) . . ? O16 C14 C4 111.70(10) . . ? C14 O16 C17 116.27(11) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C5 O1 C2 N3 0.10(12) . . . . ? C5 O1 C2 C6 178.94(9) . . . . ? O1 C2 N3 C4 0.04(12) . . . . ? C6 C2 N3 C4 -178.64(11) . . . . ? C2 N3 C4 C5 -0.16(13) . . . . ? C2 N3 C4 C14 177.38(10) . . . . ? N3 C4 C5 O1 0.22(13) . . . . ? C14 C4 C5 O1 -177.23(10) . . . . ? N3 C4 C5 C18 179.67(12) . . . . ? C14 C4 C5 C18 2.2(2) . . . . ? C2 O1 C5 C4 -0.19(11) . . . . ? C2 O1 C5 C18 -179.76(10) . . . . ? N3 C2 C6 C7 -178.00(11) . . . . ? O1 C2 C6 C7 3.36(16) . . . . ? N3 C2 C6 C11 2.55(18) . . . . ? O1 C2 C6 C11 -176.08(9) . . . . ? C11 C6 C7 C8 1.06(17) . . . . ? C2 C6 C7 C8 -178.39(10) . . . . ? C6 C7 C8 C9 0.08(17) . . . . ? C7 C8 C9 O12 178.82(10) . . . . ? C7 C8 C9 C10 -1.52(17) . . . . ? O12 C9 C10 C11 -178.56(10) . . . . ? C8 C9 C10 C11 1.81(17) . . . . ? C9 C10 C11 C6 -0.67(17) . . . . ? C7 C6 C11 C10 -0.77(17) . . . . ? C2 C6 C11 C10 178.70(10) . . . . ? C10 C9 O12 C13 8.80(16) . . . . ? C8 C9 O12 C13 -171.56(10) . . . . ? C5 C4 C14 O15 -3.5(2) . . . . ? N3 C4 C14 O15 179.41(11) . . . . ? C5 C4 C14 O16 176.45(11) . . . . ? N3 C4 C14 O16 -0.68(16) . . . . ? O15 C14 O16 C17 1.25(18) . . . . ? C4 C14 O16 C17 -178.66(10) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.35 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.06 #===END of CIF # Attachment 'Cpd_5b.CIF' data_anoxme _database_code_depnum_ccdc_archive 'CCDC 721493' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O4' _chemical_formula_sum 'C13 H13 N O4' _chemical_formula_weight 247.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.2324(14) _cell_length_b 7.1119(8) _cell_length_c 13.548(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.188(2) _cell_angle_gamma 90.00 _cell_volume 1178.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2357 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.9 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.104 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7364 _diffrn_reflns_av_R_equivalents 0.097 _diffrn_reflns_av_sigmaI/netI 0.078 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2655 _reflns_number_gt 1808 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; ; _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^)+(0.053P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'sp2-bound methyl H atoms from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0077(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2655 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.117 _refine_ls_wR_factor_gt 0.105 _refine_ls_goodness_of_fit_ref 0.94 _refine_ls_restrained_S_all 0.94 _refine_ls_shift/su_max 0.001 _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 O1 O 0.44557(8) 0.25225(14) 0.93081(8) 0.0261(3) Uani 1 1 d . . . C2 C 0.53798(12) 0.1860(2) 0.88837(11) 0.0252(3) Uani 1 1 d . . . N3 N 0.52589(10) 0.14459(18) 0.79495(9) 0.0280(3) Uani 1 1 d . . . C4 C 0.41706(12) 0.1847(2) 0.77225(11) 0.0274(4) Uani 1 1 d . . . C5 C 0.36914(12) 0.2512(2) 0.85484(11) 0.0265(4) Uani 1 1 d . . . C6 C 0.63672(12) 0.1717(2) 0.94984(11) 0.0247(3) Uani 1 1 d . . . C7 C 0.73450(12) 0.1129(2) 0.90768(11) 0.0273(4) Uani 1 1 d . . . H7A H 0.7358 0.0825 0.8394 0.033 Uiso 1 1 calc R . . C8 C 0.82893(12) 0.0987(2) 0.96449(12) 0.0288(4) Uani 1 1 d . . . H8A H 0.8951 0.0597 0.9352 0.035 Uiso 1 1 calc R . . C9 C 0.82739(12) 0.1417(2) 1.06489(11) 0.0270(4) Uani 1 1 d . . . C10 C 0.73065(12) 0.1984(2) 1.10812(12) 0.0277(4) Uani 1 1 d . . . H10A H 0.7291 0.2260 1.1767 0.033 Uiso 1 1 calc R . . C11 C 0.63635(12) 0.2140(2) 1.04996(11) 0.0273(4) Uani 1 1 d . . . H11A H 0.5704 0.2544 1.0791 0.033 Uiso 1 1 calc R . . O12 O 0.92530(8) 0.12380(17) 1.11446(8) 0.0352(3) Uani 1 1 d . . . C13 C 0.92692(14) 0.1657(3) 1.21771(13) 0.0420(5) Uani 1 1 d . . . H13A H 1.0012 0.1487 1.2447 0.063 Uiso 1 1 calc R . . H13B H 0.8768 0.0810 1.2516 0.063 Uiso 1 1 calc R . . H13C H 0.9038 0.2962 1.2276 0.063 Uiso 1 1 calc R . . C14 C 0.36873(14) 0.1511(2) 0.67236(12) 0.0354(4) Uani 1 1 d . . . H14A H 0.2916 0.1162 0.6782 0.053 Uiso 1 1 calc R . . H14B H 0.4083 0.0490 0.6402 0.053 Uiso 1 1 calc R . . H14C H 0.3744 0.2659 0.6328 0.053 Uiso 1 1 calc R . . C15 C 0.25602(12) 0.3056(2) 0.87244(12) 0.0279(4) Uani 1 1 d . . . O16 O 0.18756(9) 0.31864(18) 0.80730(9) 0.0420(3) Uani 1 1 d . . . O17 O 0.23781(8) 0.33696(16) 0.96814(8) 0.0307(3) Uani 1 1 d . . . C18 C 0.12553(13) 0.3799(3) 0.99164(14) 0.0396(5) Uani 1 1 d . . . H18A H 0.1201 0.4017 1.0628 0.059 Uiso 1 1 calc R . . H18B H 0.0785 0.2740 0.9723 0.059 Uiso 1 1 calc R . . H18C H 0.1020 0.4929 0.9557 0.059 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 O1 0.0186(5) 0.0338(6) 0.0260(5) 0.0010(4) -0.0023(4) 0.0003(4) C2 0.0220(7) 0.0258(8) 0.0277(8) 0.0026(6) 0.0010(6) -0.0005(6) N3 0.0242(7) 0.0326(8) 0.0272(7) 0.0013(5) -0.0024(5) -0.0006(5) C4 0.0263(8) 0.0299(9) 0.0260(8) 0.0033(6) -0.0030(6) -0.0036(7) C5 0.0229(8) 0.0306(9) 0.0260(8) 0.0036(6) -0.0046(6) -0.0032(6) C6 0.0215(7) 0.0247(8) 0.0278(8) 0.0033(6) -0.0019(6) -0.0013(6) C7 0.0256(8) 0.0301(9) 0.0264(8) 0.0013(6) 0.0018(6) 0.0001(7) C8 0.0225(7) 0.0308(9) 0.0332(8) 0.0029(7) 0.0030(7) 0.0022(6) C9 0.0201(7) 0.0290(9) 0.0317(8) 0.0047(7) -0.0037(6) -0.0020(6) C10 0.0236(8) 0.0334(9) 0.0261(8) 0.0002(6) -0.0002(6) 0.0003(6) C11 0.0198(7) 0.0328(9) 0.0293(8) 0.0004(7) 0.0011(6) 0.0010(6) O12 0.0198(6) 0.0509(8) 0.0345(6) 0.0018(5) -0.0044(5) 0.0035(5) C13 0.0262(9) 0.0635(13) 0.0359(10) -0.0003(9) -0.0113(7) -0.0002(8) C14 0.0326(9) 0.0465(11) 0.0269(8) -0.0026(7) -0.0043(7) -0.0020(8) C15 0.0234(8) 0.0308(9) 0.0293(8) 0.0039(7) -0.0048(7) -0.0036(6) O16 0.0264(6) 0.0627(9) 0.0365(7) 0.0040(6) -0.0092(5) 0.0009(6) O17 0.0210(5) 0.0409(7) 0.0303(6) 0.0005(5) 0.0002(5) 0.0012(5) C18 0.0235(8) 0.0476(11) 0.0480(11) 0.0013(9) 0.0076(8) 0.0045(7) _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 O1 C2 1.3628(17) . ? O1 C5 1.3760(18) . ? C2 N3 1.305(2) . ? C2 C6 1.456(2) . ? N3 C4 1.390(2) . ? C4 C5 1.359(2) . ? C4 C14 1.485(2) . ? C5 C15 1.461(2) . ? C6 C11 1.390(2) . ? C6 C7 1.400(2) . ? C7 C8 1.378(2) . ? C7 H7A 0.9500 . ? C8 C9 1.395(2) . ? C8 H8A 0.9500 . ? C9 O12 1.3668(18) . ? C9 C10 1.391(2) . ? C10 C11 1.388(2) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? O12 C13 1.430(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O16 1.2075(19) . ? C15 O17 1.339(2) . ? O17 C18 1.4488(18) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 103.84(11) . . ? N3 C2 O1 114.14(13) . . ? N3 C2 C6 127.94(14) . . ? O1 C2 C6 117.92(13) . . ? C2 N3 C4 104.90(13) . . ? C5 C4 N3 108.47(14) . . ? C5 C4 C14 129.50(14) . . ? N3 C4 C14 122.02(14) . . ? C4 C5 O1 108.65(13) . . ? C4 C5 C15 130.75(15) . . ? O1 C5 C15 120.50(13) . . ? C11 C6 C7 118.88(14) . . ? C11 C6 C2 121.58(14) . . ? C7 C6 C2 119.54(14) . . ? C8 C7 C6 120.47(14) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C7 C8 C9 120.03(14) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? O12 C9 C10 124.38(14) . . ? O12 C9 C8 115.42(13) . . ? C10 C9 C8 120.20(14) . . ? C11 C10 C9 119.25(14) . . ? C11 C10 H10A 120.4 . . ? C9 C10 H10A 120.4 . . ? C10 C11 C6 121.15(14) . . ? C10 C11 H11A 119.4 . . ? C6 C11 H11A 119.4 . . ? C9 O12 C13 117.09(12) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O16 C15 O17 124.63(14) . . ? O16 C15 C5 123.08(14) . . ? O17 C15 C5 112.29(14) . . ? C15 O17 C18 115.18(13) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C5 O1 C2 N3 -0.11(17) . . . . ? C5 O1 C2 C6 179.18(13) . . . . ? O1 C2 N3 C4 -0.32(17) . . . . ? C6 C2 N3 C4 -179.52(15) . . . . ? C2 N3 C4 C5 0.63(17) . . . . ? C2 N3 C4 C14 -178.17(14) . . . . ? N3 C4 C5 O1 -0.72(17) . . . . ? C14 C4 C5 O1 177.96(15) . . . . ? N3 C4 C5 C15 -176.92(16) . . . . ? C14 C4 C5 C15 1.8(3) . . . . ? C2 O1 C5 C4 0.51(16) . . . . ? C2 O1 C5 C15 177.17(14) . . . . ? N3 C2 C6 C11 -177.36(15) . . . . ? O1 C2 C6 C11 3.5(2) . . . . ? N3 C2 C6 C7 2.2(3) . . . . ? O1 C2 C6 C7 -176.94(13) . . . . ? C11 C6 C7 C8 -0.5(2) . . . . ? C2 C6 C7 C8 179.87(14) . . . . ? C6 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 O12 -179.79(13) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? O12 C9 C10 C11 179.10(14) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C9 C10 C11 C6 0.9(2) . . . . ? C7 C6 C11 C10 -0.2(2) . . . . ? C2 C6 C11 C10 179.41(14) . . . . ? C10 C9 O12 C13 0.3(2) . . . . ? C8 C9 O12 C13 -179.68(14) . . . . ? C4 C5 C15 O16 -9.0(3) . . . . ? O1 C5 C15 O16 175.14(14) . . . . ? C4 C5 C15 O17 170.36(15) . . . . ? O1 C5 C15 O17 -5.5(2) . . . . ? O16 C15 O17 C18 3.2(2) . . . . ? C5 C15 O17 C18 -176.23(14) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.22 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.05 #===END of CIF # Attachment 'Cpd_7.CIF' data_ampome _database_code_depnum_ccdc_archive 'CCDC 721494' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N O5 P' _chemical_formula_sum 'C12 H16 N O5 P' _chemical_formula_weight 285.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.2037(9) _cell_length_b 8.6712(4) _cell_length_c 20.5323(11) _cell_angle_alpha 90.00 _cell_angle_beta 114.006(2) _cell_angle_gamma 90.00 _cell_volume 2798.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3850 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.9 _exptl_crystal_description 'kite-shaped plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details '(Bruker SHELXTL; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 12210 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.015 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3210 _reflns_number_gt 2994 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)' _refine_special_details ; ; _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^)+(0.061P)^2^+1.672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'N-H from delta-F; Me from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'N-H freely refined; rigid rotor for all Me; riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3210 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.001 _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 C1 C 0.18294(10) 0.63218(16) 0.54872(7) 0.0338(3) Uani 1 1 d . . . H1A H 0.2122 0.7254 0.5436 0.051 Uiso 1 1 calc R . . H1B H 0.2210 0.5730 0.5901 0.051 Uiso 1 1 calc R . . H1C H 0.1318 0.6614 0.5556 0.051 Uiso 1 1 calc R . . C2 C 0.15828(8) 0.53565(14) 0.48288(7) 0.0248(2) Uani 1 1 d . . . O3 O 0.17398(7) 0.57137(12) 0.43270(6) 0.0391(3) Uani 1 1 d . . . C4 C 0.10861(7) 0.38786(13) 0.48074(6) 0.0198(2) Uani 1 1 d . . . H4 H 0.0494 0.4195 0.4723 0.024 Uiso 1 1 calc R . . P5 P 0.100438(18) 0.25758(4) 0.408693(15) 0.02185(11) Uani 1 1 d . . . O6 O 0.18278(6) 0.21388(12) 0.40841(5) 0.0300(2) Uani 1 1 d . . . O7 O 0.03937(6) 0.33187(12) 0.33687(5) 0.0313(2) Uani 1 1 d . . . C8 C -0.04987(8) 0.35982(18) 0.31910(7) 0.0359(3) Uani 1 1 d . . . H8A H -0.0759 0.2664 0.3283 0.054 Uiso 1 1 calc R . . H8B H -0.0785 0.3875 0.2686 0.054 Uiso 1 1 calc R . . H8C H -0.0557 0.4445 0.3484 0.054 Uiso 1 1 calc R . . O9 O 0.04779(6) 0.11776(11) 0.41863(5) 0.0310(2) Uani 1 1 d . . . C10 C 0.08930(10) -0.01971(17) 0.45656(9) 0.0403(3) Uani 1 1 d . . . H10A H 0.1511 -0.0073 0.4743 0.060 Uiso 1 1 calc R . . H10B H 0.0713 -0.1085 0.4243 0.060 Uiso 1 1 calc R . . H10C H 0.0736 -0.0366 0.4968 0.060 Uiso 1 1 calc R . . N11 N 0.14269(6) 0.30316(12) 0.54755(5) 0.0208(2) Uani 1 1 d . . . H11N H 0.1939(12) 0.279(2) 0.5634(9) 0.034(4) Uiso 1 1 d . . . C12 C 0.09447(7) 0.27767(13) 0.58458(6) 0.0202(2) Uani 1 1 d . . . O13 O 0.02332(5) 0.33399(10) 0.56687(5) 0.0268(2) Uani 1 1 d . . . C14 C 0.13163(7) 0.17324(14) 0.64829(6) 0.0227(2) Uani 1 1 d . . . C15 C 0.09259(9) 0.17183(16) 0.69611(7) 0.0304(3) Uani 1 1 d . . . H15 H 0.0463 0.2392 0.6890 0.036 Uiso 1 1 calc R . . C16 C 0.12150(10) 0.07187(19) 0.75397(7) 0.0384(3) Uani 1 1 d . . . H16 H 0.0953 0.0720 0.7868 0.046 Uiso 1 1 calc R . . C17 C 0.18808(10) -0.02762(18) 0.76406(7) 0.0383(3) Uani 1 1 d . . . H17 H 0.2071 -0.0968 0.8033 0.046 Uiso 1 1 calc R . . C18 C 0.22722(9) -0.02667(17) 0.71700(7) 0.0362(3) Uani 1 1 d . . . H18 H 0.2732 -0.0948 0.7242 0.043 Uiso 1 1 calc R . . C19 C 0.19937(8) 0.07388(15) 0.65905(7) 0.0285(3) Uani 1 1 d . . . H19 H 0.2265 0.0746 0.6270 0.034 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 C1 0.0416(7) 0.0270(6) 0.0316(7) -0.0022(5) 0.0136(6) -0.0073(5) C2 0.0238(6) 0.0235(5) 0.0268(6) 0.0035(4) 0.0100(5) -0.0004(4) O3 0.0513(6) 0.0374(5) 0.0371(5) 0.0014(4) 0.0268(5) -0.0124(5) C4 0.0193(5) 0.0222(5) 0.0188(5) 0.0022(4) 0.0085(4) 0.0009(4) P5 0.01755(17) 0.02767(18) 0.02036(17) -0.00153(11) 0.00773(13) -0.00034(10) O6 0.0217(4) 0.0401(5) 0.0295(5) -0.0064(4) 0.0117(4) 0.0010(4) O7 0.0251(5) 0.0460(6) 0.0207(4) 0.0021(4) 0.0069(4) 0.0027(4) C8 0.0254(6) 0.0481(8) 0.0279(6) -0.0039(6) 0.0043(5) 0.0091(6) O9 0.0236(4) 0.0284(5) 0.0384(5) -0.0020(4) 0.0101(4) -0.0045(3) C10 0.0409(8) 0.0270(7) 0.0470(8) 0.0017(6) 0.0116(7) -0.0045(6) N11 0.0172(5) 0.0252(5) 0.0200(5) 0.0047(4) 0.0075(4) 0.0022(4) C12 0.0213(5) 0.0201(5) 0.0194(5) -0.0007(4) 0.0084(4) -0.0015(4) O13 0.0233(4) 0.0304(5) 0.0307(5) 0.0060(4) 0.0151(4) 0.0044(3) C14 0.0235(6) 0.0242(5) 0.0187(5) 0.0012(4) 0.0068(4) -0.0038(4) C15 0.0316(7) 0.0362(7) 0.0255(6) 0.0020(5) 0.0138(5) -0.0027(5) C16 0.0442(8) 0.0489(8) 0.0240(6) 0.0051(6) 0.0159(6) -0.0075(7) C17 0.0418(8) 0.0404(8) 0.0240(6) 0.0111(5) 0.0045(5) -0.0066(6) C18 0.0324(7) 0.0363(7) 0.0330(7) 0.0114(6) 0.0061(6) 0.0042(5) C19 0.0276(6) 0.0305(6) 0.0266(6) 0.0054(5) 0.0102(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.4970(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O3 1.2070(16) . ? C2 C4 1.5310(16) . ? C4 N11 1.4528(14) . ? C4 P5 1.8207(11) . ? C4 H4 1.0000 . ? P5 O6 1.4687(9) . ? P5 O7 1.5598(9) . ? P5 O9 1.5755(9) . ? O7 C8 1.4467(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O9 C10 1.4439(17) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N11 C12 1.3520(15) . ? N11 H11N 0.831(18) . ? C12 O13 1.2276(14) . ? C12 C14 1.5032(15) . ? C14 C19 1.3928(17) . ? C14 C15 1.3969(17) . ? C15 C16 1.3891(19) . ? C15 H15 0.9500 . ? C16 C17 1.381(2) . ? C16 H16 0.9500 . ? C17 C18 1.384(2) . ? C17 H17 0.9500 . ? C18 C19 1.3934(18) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 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 . . ? O3 C2 C1 123.20(11) . . ? O3 C2 C4 120.42(11) . . ? C1 C2 C4 116.35(10) . . ? N11 C4 C2 112.95(9) . . ? N11 C4 P5 108.76(8) . . ? C2 C4 P5 113.61(8) . . ? N11 C4 H4 107.0 . . ? C2 C4 H4 107.0 . . ? P5 C4 H4 107.0 . . ? O6 P5 O7 112.50(5) . . ? O6 P5 O9 114.09(6) . . ? O7 P5 O9 103.80(5) . . ? O6 P5 C4 114.05(5) . . ? O7 P5 C4 108.15(5) . . ? O9 P5 C4 103.34(5) . . ? C8 O7 P5 123.03(8) . . ? O7 C8 H8A 109.5 . . ? O7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 O9 P5 121.39(8) . . ? O9 C10 H10A 109.5 . . ? O9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 N11 C4 120.62(10) . . ? C12 N11 H11N 122.3(12) . . ? C4 N11 H11N 116.8(12) . . ? O13 C12 N11 122.30(10) . . ? O13 C12 C14 121.14(10) . . ? N11 C12 C14 116.54(10) . . ? C19 C14 C15 119.58(11) . . ? C19 C14 C12 122.87(11) . . ? C15 C14 C12 117.46(11) . . ? C16 C15 C14 119.96(13) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 C15 120.31(13) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.06(12) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.26(13) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C14 C19 C18 119.82(12) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? 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 O3 C2 C4 N11 138.40(12) . . . . ? C1 C2 C4 N11 -43.33(14) . . . . ? O3 C2 C4 P5 13.92(15) . . . . ? C1 C2 C4 P5 -167.81(9) . . . . ? N11 C4 P5 O6 -71.31(9) . . . . ? C2 C4 P5 O6 55.40(10) . . . . ? N11 C4 P5 O7 162.73(7) . . . . ? C2 C4 P5 O7 -70.56(9) . . . . ? N11 C4 P5 O9 53.11(8) . . . . ? C2 C4 P5 O9 179.82(8) . . . . ? O6 P5 O7 C8 168.85(10) . . . . ? O9 P5 O7 C8 45.02(12) . . . . ? C4 P5 O7 C8 -64.29(12) . . . . ? O6 P5 O9 C10 27.75(12) . . . . ? O7 P5 O9 C10 150.54(10) . . . . ? C4 P5 O9 C10 -96.64(11) . . . . ? C2 C4 N11 C12 119.07(11) . . . . ? P5 C4 N11 C12 -113.85(10) . . . . ? C4 N11 C12 O13 -5.74(17) . . . . ? C4 N11 C12 C14 172.98(10) . . . . ? O13 C12 C14 C19 161.46(12) . . . . ? N11 C12 C14 C19 -17.27(17) . . . . ? O13 C12 C14 C15 -15.07(17) . . . . ? N11 C12 C14 C15 166.20(11) . . . . ? C19 C14 C15 C16 0.09(19) . . . . ? C12 C14 C15 C16 176.74(12) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 0.9(2) . . . . ? C16 C17 C18 C19 -0.4(2) . . . . ? C15 C14 C19 C18 0.44(19) . . . . ? C12 C14 C19 C18 -176.02(12) . . . . ? C17 C18 C19 C14 -0.3(2) . . . . ? 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 N11 H11N O6 0.83(2) 1.96(2) 2.7651(14) 163(2) 7_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.38 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.05 #===END of CIF # Attachment 'Cpd_9f.CIF' data_thinpo _database_code_depnum_ccdc_archive 'CCDC 721495' _refine_special_details ; Disorder was identified in the thiophene ring: this was modelled using partial linked occupancies and similarity restraints between equivalent distances in the two disorder components. The major and minor components refined to 0.726(2) and 0.274(2), respectively. ; _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N O4 P S' _chemical_formula_sum 'C14 H14 N O4 P S' _chemical_formula_weight 323.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.561(2) _cell_length_b 5.7605(6) _cell_length_c 12.8043(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.171(2) _cell_angle_gamma 90.00 _cell_volume 1449.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2770 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 26.7 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.348 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12932 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3328 _reflns_number_gt 2903 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)' _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^)+(0.062P)^2^+0.182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'sp2-bound methyl group from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3328 _refine_ls_number_parameters 210 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.106 _refine_ls_wR_factor_gt 0.102 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.22131(5) 1.03231(18) -0.00415(8) 0.0270(2) Uani 1 1 d U . . C2 C 0.27116(7) 0.9602(3) -0.04584(11) 0.0257(3) Uani 1 1 d U A . N3 N 0.27524(7) 1.0751(2) -0.13066(10) 0.0308(3) Uani 1 1 d U . . C4 C 0.22428(8) 1.2419(3) -0.14827(12) 0.0290(3) Uani 1 1 d U . . C5 C 0.19135(8) 1.2161(3) -0.07163(12) 0.0274(3) Uani 1 1 d U . . C6 C 0.31302(7) 0.7659(3) 0.00559(12) 0.0264(3) Uani 1 1 d DU . . C7 C 0.31404(15) 0.6443(5) 0.0930(3) 0.0292(6) Uani 0.726(2) 1 d PDU A 1 H7 H 0.2838 0.6763 0.1347 0.035 Uiso 0.726(2) 1 calc PR A 1 C7' C 0.3616(4) 0.6495(12) -0.0194(7) 0.0357(16) Uani 0.274(2) 1 d PDU A 2 H7' H 0.3737 0.6974 -0.0822 0.043 Uiso 0.274(2) 1 calc PR A 2 C8 C 0.36398(7) 0.4582(3) 0.12246(14) 0.0319(3) Uani 1 1 d DU . . C9 C 0.38179(9) 0.2950(3) 0.20698(14) 0.0375(4) Uani 1 1 d U A . H9 H 0.3599 0.2950 0.2628 0.045 Uiso 1 1 calc R . . C10 C 0.43159(9) 0.1341(3) 0.20809(14) 0.0379(4) Uani 1 1 d U . . H10 H 0.4441 0.0225 0.2652 0.045 Uiso 1 1 calc R A . C11 C 0.46398(9) 0.1330(3) 0.12613(14) 0.0357(4) Uani 1 1 d U A . H11 H 0.4982 0.0207 0.1285 0.043 Uiso 1 1 calc R . . C12 C 0.44722(8) 0.2909(3) 0.04280(13) 0.0335(3) Uani 1 1 d U . . H12 H 0.4691 0.2882 -0.0129 0.040 Uiso 1 1 calc R A . C13 C 0.39725(8) 0.4565(3) 0.04114(12) 0.0295(3) Uani 1 1 d DU A . S14 S 0.37179(3) 0.66946(11) -0.06003(6) 0.0286(2) Uani 0.726(2) 1 d PDU A 1 S14' S 0.30472(10) 0.6528(3) 0.13326(17) 0.0274(5) Uani 0.274(2) 1 d PDU A 2 P15 P 0.11969(2) 1.35877(7) -0.05237(3) 0.02980(13) Uani 1 1 d U . . O16 O 0.09038(6) 1.5224(2) -0.14051(10) 0.0424(3) Uani 1 1 d U . . O17 O 0.06909(5) 1.16554(19) -0.03664(9) 0.0330(3) Uani 1 1 d U . . C18 C 0.02849(9) 1.0417(3) -0.13251(14) 0.0386(4) Uani 1 1 d U . . H18A H -0.0003 0.9275 -0.1106 0.058 Uiso 1 1 calc R . . H18B H 0.0586 0.9619 -0.1675 0.058 Uiso 1 1 calc R . . H18C H -0.0003 1.1521 -0.1841 0.058 Uiso 1 1 calc R . . O19 O 0.14703(6) 1.4593(2) 0.06634(9) 0.0377(3) Uani 1 1 d U . . C20 C 0.10236(10) 1.5883(4) 0.11311(15) 0.0482(5) Uani 1 1 d U . . H20A H 0.1275 1.6377 0.1873 0.072 Uiso 1 1 calc R . . H20B H 0.0641 1.4896 0.1159 0.072 Uiso 1 1 calc R . . H20C H 0.0851 1.7251 0.0680 0.072 Uiso 1 1 calc R . . C21 C 0.21298(9) 1.4141(3) -0.23841(14) 0.0403(4) Uani 1 1 d U . . H21A H 0.1651 1.4624 -0.2612 0.060 Uiso 1 1 calc R . . H21B H 0.2243 1.3436 -0.3005 0.060 Uiso 1 1 calc R . . H21C H 0.2421 1.5498 -0.2129 0.060 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 O1 0.0286(5) 0.0258(5) 0.0276(5) 0.0024(4) 0.0099(4) 0.0073(4) C2 0.0249(7) 0.0252(7) 0.0274(7) -0.0052(6) 0.0082(6) -0.0003(5) N3 0.0327(7) 0.0301(7) 0.0305(7) -0.0010(5) 0.0106(5) -0.0009(5) C4 0.0314(8) 0.0254(7) 0.0275(7) -0.0006(6) 0.0046(6) -0.0019(6) C5 0.0296(7) 0.0224(7) 0.0281(7) 0.0010(6) 0.0050(6) 0.0050(6) C6 0.0244(7) 0.0243(7) 0.0310(7) -0.0043(6) 0.0087(6) 0.0008(6) C7 0.0259(13) 0.0301(12) 0.0350(16) -0.0077(12) 0.0144(12) 0.0001(9) C7' 0.038(4) 0.039(4) 0.035(4) -0.001(3) 0.017(3) -0.002(3) C8 0.0242(7) 0.0257(8) 0.0457(9) -0.0092(6) 0.0103(7) -0.0020(6) C9 0.0396(9) 0.0340(8) 0.0432(9) -0.0069(7) 0.0188(8) -0.0069(7) C10 0.0434(10) 0.0294(8) 0.0366(9) 0.0020(7) 0.0053(7) -0.0013(7) C11 0.0316(8) 0.0273(8) 0.0446(9) -0.0061(7) 0.0058(7) 0.0071(6) C12 0.0330(8) 0.0311(8) 0.0373(8) -0.0066(7) 0.0120(7) 0.0026(6) C13 0.0272(7) 0.0250(7) 0.0329(8) -0.0031(6) 0.0034(6) -0.0002(6) S14 0.0297(3) 0.0289(3) 0.0305(4) 0.0001(2) 0.0138(3) 0.0069(2) S14' 0.0259(8) 0.0244(8) 0.0330(11) 0.0014(7) 0.0106(7) 0.0062(5) P15 0.0301(2) 0.0253(2) 0.0308(2) -0.00201(15) 0.00384(17) 0.00806(15) O16 0.0458(7) 0.0311(6) 0.0440(7) 0.0047(5) 0.0037(5) 0.0131(5) O17 0.0308(6) 0.0337(6) 0.0335(6) -0.0044(5) 0.0078(5) 0.0048(4) C18 0.0396(9) 0.0318(9) 0.0426(9) -0.0112(7) 0.0094(7) 0.0008(7) O19 0.0345(6) 0.0382(7) 0.0360(6) -0.0106(5) 0.0036(5) 0.0092(5) C20 0.0496(11) 0.0493(11) 0.0445(10) -0.0160(8) 0.0121(9) 0.0124(9) C21 0.0457(10) 0.0373(9) 0.0351(9) 0.0091(7) 0.0075(7) -0.0019(8) _geom_special_details ; ; 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 O1 C2 1.3531(17) . ? O1 C5 1.3901(17) . ? C2 N3 1.2956(19) . ? C2 C6 1.446(2) . ? N3 C4 1.390(2) . ? C4 C5 1.355(2) . ? C4 C21 1.487(2) . ? C5 P15 1.7669(15) . ? C6 C7 1.315(4) . ? C6 C7' 1.318(7) . ? C6 S14 1.7534(15) . ? C6 S14' 1.814(2) . ? C7 C8 1.455(3) . ? C7 H7 0.9500 . ? C7' C13 1.428(6) . ? C7' H7' 0.9500 . ? C8 C9 1.398(2) . ? C8 C13 1.405(2) . ? C8 S14' 1.691(2) . ? C9 C10 1.378(2) . ? C9 H9 0.9500 . ? C10 C11 1.399(3) . ? C10 H10 0.9500 . ? C11 C12 1.367(2) . ? C11 H11 0.9500 . ? C12 C13 1.398(2) . ? C12 H12 0.9500 . ? C13 S14 1.7482(17) . ? P15 O16 1.4574(12) . ? P15 O19 1.5676(11) . ? P15 O17 1.5766(12) . ? O17 C18 1.4517(19) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O19 C20 1.442(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 103.70(11) . . ? N3 C2 O1 114.70(13) . . ? N3 C2 C6 126.86(14) . . ? O1 C2 C6 118.44(13) . . ? C2 N3 C4 104.89(13) . . ? C5 C4 N3 108.68(13) . . ? C5 C4 C21 129.67(15) . . ? N3 C4 C21 121.64(14) . . ? C4 C5 O1 108.02(13) . . ? C4 C5 P15 131.72(12) . . ? O1 C5 P15 120.15(10) . . ? C7 C6 C2 131.10(17) . . ? C7' C6 C2 132.4(4) . . ? C7 C6 S14 113.50(16) . . ? C2 C6 S14 115.39(11) . . ? C7' C6 S14' 108.4(4) . . ? C2 C6 S14' 119.11(12) . . ? C6 C7 C8 116.5(2) . . ? C6 C7 H7 121.8 . . ? C8 C7 H7 121.8 . . ? C6 C7' C13 124.7(7) . . ? C6 C7' H7' 117.7 . . ? C13 C7' H7' 117.7 . . ? C9 C8 C13 119.70(14) . . ? C9 C8 C7 134.42(19) . . ? C13 C8 C7 105.87(19) . . ? C9 C8 S14' 114.39(14) . . ? C13 C8 S14' 125.84(15) . . ? C10 C9 C8 118.97(15) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 120.79(15) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 121.10(15) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 118.75(15) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 C8 120.68(14) . . ? C8 C13 C7' 96.4(4) . . ? C12 C13 S14 123.23(13) . . ? C8 C13 S14 116.08(12) . . ? C13 S14 C6 88.01(8) . . ? C8 S14' C6 84.42(12) . . ? O16 P15 O19 117.38(7) . . ? O16 P15 O17 114.71(7) . . ? O19 P15 O17 101.43(7) . . ? O16 P15 C5 111.35(7) . . ? O19 P15 C5 103.42(6) . . ? O17 P15 C5 107.35(7) . . ? C18 O17 P15 118.38(10) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 O19 P15 120.20(11) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 C21 H21A 109.5 . . ? C4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C2 N3 -0.48(16) . . . . ? C5 O1 C2 C6 -179.58(12) . . . . ? O1 C2 N3 C4 0.58(17) . . . . ? C6 C2 N3 C4 179.59(14) . . . . ? C2 N3 C4 C5 -0.44(17) . . . . ? C2 N3 C4 C21 178.86(14) . . . . ? N3 C4 C5 O1 0.17(17) . . . . ? C21 C4 C5 O1 -179.06(15) . . . . ? N3 C4 C5 P15 -176.04(12) . . . . ? C21 C4 C5 P15 4.7(3) . . . . ? C2 O1 C5 C4 0.16(15) . . . . ? C2 O1 C5 P15 176.89(10) . . . . ? N3 C2 C6 C7 177.6(2) . . . . ? O1 C2 C6 C7 -3.4(3) . . . . ? N3 C2 C6 C7' -3.7(5) . . . . ? O1 C2 C6 C7' 175.3(5) . . . . ? N3 C2 C6 S14 -3.8(2) . . . . ? O1 C2 C6 S14 175.15(10) . . . . ? N3 C2 C6 S14' 172.91(14) . . . . ? O1 C2 C6 S14' -8.11(19) . . . . ? C2 C6 C7 C8 -179.62(16) . . . . ? S14 C6 C7 C8 1.8(3) . . . . ? C2 C6 C7' C13 -179.0(3) . . . . ? S14' C6 C7' C13 4.2(7) . . . . ? C6 C7 C8 C9 179.25(19) . . . . ? C6 C7 C8 C13 -2.3(3) . . . . ? C13 C8 C9 C10 -0.5(2) . . . . ? C7 C8 C9 C10 177.8(2) . . . . ? S14' C8 C9 C10 -177.54(14) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 0.6(2) . . . . ? C11 C12 C13 C8 -1.1(2) . . . . ? C11 C12 C13 C7' 179.7(5) . . . . ? C11 C12 C13 S14 179.37(12) . . . . ? C9 C8 C13 C12 1.0(2) . . . . ? C7 C8 C13 C12 -177.69(17) . . . . ? S14' C8 C13 C12 177.77(14) . . . . ? C9 C8 C13 C7' -179.4(3) . . . . ? S14' C8 C13 C7' -2.7(4) . . . . ? C9 C8 C13 S14 -179.40(12) . . . . ? C7 C8 C13 S14 1.86(19) . . . . ? C6 C7' C13 C12 177.9(3) . . . . ? C6 C7' C13 C8 -1.4(7) . . . . ? C12 C13 S14 C6 178.65(14) . . . . ? C8 C13 S14 C6 -0.89(13) . . . . ? C7 C6 S14 C13 -0.51(17) . . . . ? C2 C6 S14 C13 -179.35(12) . . . . ? C9 C8 S14' C6 -178.87(13) . . . . ? C13 C8 S14' C6 4.26(17) . . . . ? C7' C6 S14' C8 -4.1(4) . . . . ? C2 C6 S14' C8 178.56(13) . . . . ? C4 C5 P15 O16 4.04(18) . . . . ? O1 C5 P15 O16 -171.80(11) . . . . ? C4 C5 P15 O19 -122.90(16) . . . . ? O1 C5 P15 O19 61.27(13) . . . . ? C4 C5 P15 O17 130.36(15) . . . . ? O1 C5 P15 O17 -45.47(13) . . . . ? O16 P15 O17 C18 47.62(13) . . . . ? O19 P15 O17 C18 175.17(11) . . . . ? C5 P15 O17 C18 -76.69(12) . . . . ? O16 P15 O19 C20 57.58(16) . . . . ? O17 P15 O19 C20 -68.22(15) . . . . ? C5 P15 O19 C20 -179.39(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.39 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.05 #===END of CIF # Attachment 'Cpd_11a.CIF' data_oxsoph _database_code_depnum_ccdc_archive 'CCDC 721496' _refine_special_details ; The hydrogen atoms of the C21 methyl group were found to be disordered about the local C-C vector. This disorder was modelled using AFIX 123 and two half-occupied orientations. ; _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N O3 S' _chemical_formula_sum 'C17 H15 N O3 S' _chemical_formula_weight 313.36 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' S S 0.1246 0.1234 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1096(9) _cell_length_b 10.0737(12) _cell_length_c 10.7607(13) _cell_angle_alpha 66.986(2) _cell_angle_beta 70.896(2) _cell_angle_gamma 78.509(2) _cell_volume 762.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3293 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.224 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6735 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.027 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3425 _reflns_number_gt 3067 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)' _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^)+(0.057P)^2^+0.143P] 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 3425 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.101 _refine_ls_wR_factor_gt 0.098 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.001 _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 N1 N 0.29732(15) 0.01677(12) 0.92086(12) 0.0302(3) Uani 1 1 d . . . C2 C 0.18108(18) 0.05844(14) 1.01680(14) 0.0274(3) Uani 1 1 d . . . O3 O 0.11717(12) 0.19904(9) 0.96934(9) 0.0267(2) Uani 1 1 d . . . C4 C 0.20599(17) 0.24691(14) 0.82827(13) 0.0251(3) Uani 1 1 d . . . C5 C 0.31684(18) 0.13681(14) 0.79777(14) 0.0283(3) Uani 1 1 d . . . C6 C 0.11301(18) -0.02674(14) 1.16537(14) 0.0282(3) Uani 1 1 d . . . C7 C 0.1767(2) -0.17156(15) 1.21593(16) 0.0345(3) Uani 1 1 d . . . H7 H 0.2627 -0.2132 1.1541 0.041 Uiso 1 1 calc R . . C8 C 0.1144(2) -0.25397(16) 1.35599(17) 0.0395(4) Uani 1 1 d . . . H8 H 0.1573 -0.3525 1.3902 0.047 Uiso 1 1 calc R . . C9 C -0.0099(2) -0.19402(18) 1.44648(16) 0.0410(4) Uani 1 1 d . . . H9 H -0.0516 -0.2510 1.5429 0.049 Uiso 1 1 calc R . . C10 C -0.0741(2) -0.05048(18) 1.39664(16) 0.0407(4) Uani 1 1 d . . . H10 H -0.1599 -0.0094 1.4590 0.049 Uiso 1 1 calc R . . C11 C -0.0133(2) 0.03285(16) 1.25647(16) 0.0352(3) Uani 1 1 d . . . H11 H -0.0580 0.1309 1.2224 0.042 Uiso 1 1 calc R . . S12 S 0.16636(4) 0.42917(3) 0.73219(3) 0.02518(11) Uani 1 1 d . . . O13 O 0.23457(13) 0.44178(11) 0.58748(10) 0.0329(2) Uani 1 1 d . . . O14 O -0.01348(12) 0.47331(10) 0.78637(11) 0.0321(2) Uani 1 1 d . . . C15 C 0.29755(17) 0.51939(13) 0.77016(13) 0.0248(3) Uani 1 1 d . . . C16 C 0.22361(18) 0.59065(15) 0.86471(15) 0.0307(3) Uani 1 1 d . . . H16 H 0.1012 0.5926 0.9088 0.037 Uiso 1 1 calc R . . C17 C 0.3306(2) 0.65924(16) 0.89440(17) 0.0347(3) Uani 1 1 d . . . H17 H 0.2803 0.7095 0.9584 0.042 Uiso 1 1 calc R . . C18 C 0.51026(19) 0.65561(14) 0.83199(16) 0.0312(3) Uani 1 1 d . . . C19 C 0.58112(19) 0.58276(17) 0.73729(17) 0.0364(3) Uani 1 1 d . . . H19 H 0.7037 0.5797 0.6938 0.044 Uiso 1 1 calc R . . C20 C 0.47633(18) 0.51491(16) 0.70554(15) 0.0329(3) Uani 1 1 d . . . H20 H 0.5259 0.4659 0.6405 0.039 Uiso 1 1 calc R . . C21 C 0.6261(2) 0.72827(17) 0.8665(2) 0.0425(4) Uani 1 1 d . . . H21A H 0.5591 0.8106 0.8921 0.064 Uiso 0.50 1 calc PR . . H21B H 0.7261 0.7625 0.7845 0.064 Uiso 0.50 1 calc PR . . H21C H 0.6685 0.6589 0.9456 0.064 Uiso 0.50 1 calc PR . . H21D H 0.7434 0.6774 0.8560 0.064 Uiso 0.50 1 calc PR . . H21E H 0.5764 0.7256 0.9636 0.064 Uiso 0.50 1 calc PR . . H21F H 0.6339 0.8291 0.8025 0.064 Uiso 0.50 1 calc PR . . C22 C 0.4448(2) 0.13020(17) 0.66403(16) 0.0378(3) Uani 1 1 d . . . H22A H 0.4259 0.2180 0.5860 0.057 Uiso 1 1 calc R . . H22B H 0.4284 0.0453 0.6476 0.057 Uiso 1 1 calc R . . H22C H 0.5642 0.1230 0.6706 0.057 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 N1 0.0335(6) 0.0241(6) 0.0324(6) -0.0077(5) -0.0119(5) -0.0007(5) C2 0.0313(7) 0.0215(6) 0.0313(7) -0.0062(5) -0.0142(6) -0.0029(5) O3 0.0297(5) 0.0215(5) 0.0258(5) -0.0046(4) -0.0080(4) -0.0023(4) C4 0.0259(6) 0.0238(6) 0.0234(6) -0.0048(5) -0.0069(5) -0.0043(5) C5 0.0290(7) 0.0263(6) 0.0308(7) -0.0093(5) -0.0107(5) -0.0022(5) C6 0.0324(7) 0.0242(6) 0.0295(7) -0.0049(5) -0.0139(6) -0.0061(5) C7 0.0424(8) 0.0272(7) 0.0350(8) -0.0067(6) -0.0169(6) -0.0036(6) C8 0.0511(9) 0.0266(7) 0.0389(8) 0.0012(6) -0.0229(7) -0.0076(6) C9 0.0487(9) 0.0411(9) 0.0296(7) 0.0005(6) -0.0139(7) -0.0176(7) C10 0.0435(9) 0.0443(9) 0.0324(8) -0.0116(7) -0.0068(7) -0.0098(7) C11 0.0408(8) 0.0284(7) 0.0340(7) -0.0068(6) -0.0116(6) -0.0045(6) S12 0.02439(18) 0.02230(17) 0.02539(18) -0.00408(13) -0.00805(13) -0.00137(12) O13 0.0378(6) 0.0329(5) 0.0251(5) -0.0054(4) -0.0101(4) -0.0040(4) O14 0.0243(5) 0.0292(5) 0.0398(6) -0.0092(4) -0.0107(4) 0.0011(4) C15 0.0246(6) 0.0193(6) 0.0257(6) -0.0030(5) -0.0069(5) -0.0019(5) C16 0.0248(7) 0.0276(7) 0.0364(7) -0.0119(6) -0.0036(5) -0.0016(5) C17 0.0342(8) 0.0303(7) 0.0420(8) -0.0179(6) -0.0089(6) 0.0002(6) C18 0.0321(7) 0.0229(6) 0.0385(8) -0.0072(6) -0.0149(6) -0.0006(5) C19 0.0227(7) 0.0406(8) 0.0455(9) -0.0169(7) -0.0062(6) -0.0033(6) C20 0.0269(7) 0.0370(8) 0.0346(7) -0.0165(6) -0.0038(6) -0.0022(6) C21 0.0378(8) 0.0345(8) 0.0640(11) -0.0206(8) -0.0229(8) 0.0000(6) C22 0.0365(8) 0.0384(8) 0.0363(8) -0.0168(7) -0.0058(6) 0.0020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.2942(18) . ? N1 C5 1.3887(17) . ? C2 O3 1.3604(15) . ? C2 C6 1.4613(19) . ? O3 C4 1.3806(15) . ? C4 C5 1.3565(18) . ? C4 S12 1.7439(13) . ? C5 C22 1.4907(19) . ? C6 C11 1.389(2) . ? C6 C7 1.3980(19) . ? C7 C8 1.381(2) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? S12 O14 1.4326(10) . ? S12 O13 1.4341(10) . ? S12 C15 1.7563(14) . ? C15 C16 1.3822(19) . ? C15 C20 1.3879(19) . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.390(2) . ? C17 H17 0.9500 . ? C18 C19 1.393(2) . ? C18 C21 1.508(2) . ? C19 C20 1.382(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 H21D 0.9800 . ? C21 H21E 0.9800 . ? C21 H21F 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 105.82(11) . . ? N1 C2 O3 114.03(12) . . ? N1 C2 C6 127.90(12) . . ? O3 C2 C6 118.07(12) . . ? C2 O3 C4 103.51(10) . . ? C5 C4 O3 109.02(11) . . ? C5 C4 S12 133.99(11) . . ? O3 C4 S12 116.84(9) . . ? C4 C5 N1 107.62(12) . . ? C4 C5 C22 131.33(13) . . ? N1 C5 C22 121.04(12) . . ? C11 C6 C7 119.65(13) . . ? C11 C6 C2 121.48(13) . . ? C7 C6 C2 118.87(13) . . ? C8 C7 C6 119.82(15) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.37(15) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.00(14) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.14(15) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C6 120.01(14) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? O14 S12 O13 120.38(6) . . ? O14 S12 C4 108.47(6) . . ? O13 S12 C4 105.47(6) . . ? O14 S12 C15 108.37(6) . . ? O13 S12 C15 108.67(6) . . ? C4 S12 C15 104.34(6) . . ? C16 C15 C20 121.09(13) . . ? C16 C15 S12 120.28(10) . . ? C20 C15 S12 118.62(10) . . ? C15 C16 C17 119.11(13) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C18 121.03(13) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C19 118.58(13) . . ? C17 C18 C21 120.74(14) . . ? C19 C18 C21 120.68(13) . . ? C20 C19 C18 121.18(13) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C15 119.01(13) . . ? C19 C20 H20 120.5 . . ? C15 C20 H20 120.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C21 H21D 109.5 . . ? H21A C21 H21D 141.1 . . ? H21B C21 H21D 56.3 . . ? H21C C21 H21D 56.3 . . ? C18 C21 H21E 109.5 . . ? H21A C21 H21E 56.3 . . ? H21B C21 H21E 141.1 . . ? H21C C21 H21E 56.3 . . ? H21D C21 H21E 109.5 . . ? C18 C21 H21F 109.5 . . ? H21A C21 H21F 56.3 . . ? H21B C21 H21F 56.3 . . ? H21C C21 H21F 141.1 . . ? H21D C21 H21F 109.5 . . ? H21E C21 H21F 109.5 . . ? C5 C22 H22A 109.5 . . ? C5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C5 N1 C2 O3 0.33(15) . . . . ? C5 N1 C2 C6 -179.97(13) . . . . ? N1 C2 O3 C4 -0.03(15) . . . . ? C6 C2 O3 C4 -179.76(11) . . . . ? C2 O3 C4 C5 -0.30(14) . . . . ? C2 O3 C4 S12 -176.59(9) . . . . ? O3 C4 C5 N1 0.50(15) . . . . ? S12 C4 C5 N1 175.90(11) . . . . ? O3 C4 C5 C22 -178.44(13) . . . . ? S12 C4 C5 C22 -3.0(2) . . . . ? C2 N1 C5 C4 -0.51(15) . . . . ? C2 N1 C5 C22 178.57(13) . . . . ? N1 C2 C6 C11 -179.65(14) . . . . ? O3 C2 C6 C11 0.04(19) . . . . ? N1 C2 C6 C7 0.1(2) . . . . ? O3 C2 C6 C7 179.79(12) . . . . ? C11 C6 C7 C8 -0.3(2) . . . . ? C2 C6 C7 C8 179.93(13) . . . . ? C6 C7 C8 C9 -0.3(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C6 -0.4(2) . . . . ? C7 C6 C11 C10 0.7(2) . . . . ? C2 C6 C11 C10 -179.57(13) . . . . ? C5 C4 S12 O14 149.94(14) . . . . ? O3 C4 S12 O14 -34.94(11) . . . . ? C5 C4 S12 O13 19.73(16) . . . . ? O3 C4 S12 O13 -165.15(9) . . . . ? C5 C4 S12 C15 -94.70(15) . . . . ? O3 C4 S12 C15 80.42(10) . . . . ? O14 S12 C15 C16 13.15(13) . . . . ? O13 S12 C15 C16 145.58(11) . . . . ? C4 S12 C15 C16 -102.27(12) . . . . ? O14 S12 C15 C20 -168.12(11) . . . . ? O13 S12 C15 C20 -35.69(12) . . . . ? C4 S12 C15 C20 76.45(12) . . . . ? C20 C15 C16 C17 0.4(2) . . . . ? S12 C15 C16 C17 179.04(11) . . . . ? C15 C16 C17 C18 -0.8(2) . . . . ? C16 C17 C18 C19 0.7(2) . . . . ? C16 C17 C18 C21 -178.98(14) . . . . ? C17 C18 C19 C20 -0.1(2) . . . . ? C21 C18 C19 C20 179.55(14) . . . . ? C18 C19 C20 C15 -0.3(2) . . . . ? C16 C15 C20 C19 0.2(2) . . . . ? S12 C15 C20 C19 -178.51(11) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.42 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.05 #===END of CIF