# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_stu6009 _database_code_depnum_ccdc_archive 'CCDC 919089' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 F3 N2 O4 S' _chemical_formula_weight 350.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 6.2339(1) _cell_length_b 8.9683(2) _cell_length_c 14.0067(3) _cell_angle_alpha 81.624(2) _cell_angle_beta 89.228(2) _cell_angle_gamma 75.671(1) _cell_volume 750.42(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2403 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.453 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4639 _exptl_absorpt_correction_T_max 0.7573 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7153 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 66.67 _reflns_number_total 2534 _reflns_number_gt 2360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.3940P] 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 2534 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.8942(3) 1.1116(2) 0.78652(12) 0.0332(4) Uani 1 1 d . . . C2 C 1.0399(3) 1.2000(2) 0.78417(14) 0.0302(4) Uani 1 1 d . . . N3 N 1.0432(3) 1.2437(2) 0.87194(12) 0.0352(4) Uani 1 1 d . . . C4 C 0.8969(4) 1.1843(3) 0.92881(16) 0.0427(5) Uani 1 1 d . . . H4 H 0.8656 1.1991 0.9931 0.051 Uiso 1 1 calc R . . C5 C 0.8047(4) 1.1004(3) 0.87640(17) 0.0423(5) Uani 1 1 d . . . H5 H 0.6991 1.0448 0.8975 0.051 Uiso 1 1 calc R . . C6 C 1.1858(3) 1.2392(2) 0.70356(15) 0.0329(5) Uani 1 1 d . . . O1 O 1.3658(3) 1.2548(2) 0.72388(12) 0.0453(4) Uani 1 1 d . . . C7 C 1.1029(4) 1.2603(2) 0.60287(15) 0.0334(5) Uani 1 1 d . . . C8 C 0.8825(4) 1.3283(3) 0.57621(16) 0.0396(5) Uani 1 1 d . . . H8 H 0.7785 1.3582 0.6234 0.048 Uiso 1 1 calc R . . C9 C 0.8165(4) 1.3520(3) 0.48024(17) 0.0462(6) Uani 1 1 d . . . H9 H 0.6677 1.3990 0.4621 0.055 Uiso 1 1 calc R . . C10 C 0.9697(5) 1.3065(3) 0.41056(17) 0.0488(6) Uani 1 1 d . . . H10 H 0.9242 1.3217 0.3454 0.059 Uiso 1 1 calc R . . C11 C 1.1885(4) 1.2392(3) 0.43676(17) 0.0475(6) Uani 1 1 d . . . H11 H 1.2916 1.2085 0.3894 0.057 Uiso 1 1 calc R . . C12 C 1.2565(4) 1.2167(3) 0.53181(16) 0.0399(5) Uani 1 1 d . . . H12 H 1.4062 1.1721 0.5492 0.048 Uiso 1 1 calc R . . C13 C 1.1809(4) 1.3390(3) 0.90511(18) 0.0484(6) Uani 1 1 d . . . H13A H 1.3305 1.2757 0.9190 0.073 Uiso 1 1 calc R . . H13B H 1.1192 1.3786 0.9631 0.073 Uiso 1 1 calc R . . H13C H 1.1835 1.4255 0.8551 0.073 Uiso 1 1 calc R . . C14 C 0.8483(4) 1.0222(3) 0.71192(17) 0.0409(5) Uani 1 1 d . . . H14A H 0.7218 1.0835 0.6723 0.061 Uiso 1 1 calc R . . H14B H 0.8162 0.9263 0.7428 0.061 Uiso 1 1 calc R . . H14C H 0.9766 0.9981 0.6718 0.061 Uiso 1 1 calc R . . S1 S 0.38437(8) 0.79750(6) 0.82500(3) 0.03351(19) Uani 1 1 d . . . O2 O 0.1861(3) 0.7469(2) 0.84869(12) 0.0472(4) Uani 1 1 d . . . O3 O 0.4638(3) 0.8673(2) 0.89872(13) 0.0556(5) Uani 1 1 d . . . O4 O 0.3903(3) 0.8762(2) 0.72847(11) 0.0466(4) Uani 1 1 d . . . C15 C 0.5917(4) 0.6149(3) 0.82548(17) 0.0414(5) Uani 1 1 d . . . F1 F 0.6065(3) 0.52572(18) 0.91060(12) 0.0659(5) Uani 1 1 d . . . F2 F 0.5452(3) 0.5344(2) 0.75998(13) 0.0723(5) Uani 1 1 d . . . F3 F 0.7912(2) 0.6376(2) 0.80562(14) 0.0681(5) 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 N1 0.0302(9) 0.0327(9) 0.0364(9) -0.0064(7) 0.0047(7) -0.0067(7) C2 0.0292(10) 0.0312(10) 0.0292(10) -0.0068(8) 0.0007(8) -0.0042(8) N3 0.0373(10) 0.0353(9) 0.0309(9) -0.0086(7) 0.0006(7) -0.0026(8) C4 0.0443(13) 0.0437(12) 0.0333(11) -0.0026(9) 0.0088(9) -0.0007(10) C5 0.0367(12) 0.0405(12) 0.0447(12) 0.0012(10) 0.0125(10) -0.0052(10) C6 0.0328(12) 0.0303(10) 0.0372(11) -0.0107(8) 0.0056(9) -0.0077(8) O1 0.0343(9) 0.0600(10) 0.0478(9) -0.0162(8) 0.0046(7) -0.0190(7) C7 0.0366(11) 0.0323(10) 0.0336(10) -0.0079(8) 0.0075(9) -0.0113(9) C8 0.0402(12) 0.0412(12) 0.0372(11) -0.0091(9) 0.0081(9) -0.0082(9) C9 0.0452(14) 0.0474(13) 0.0428(12) -0.0060(10) -0.0028(10) -0.0055(11) C10 0.0631(16) 0.0513(14) 0.0330(11) -0.0080(10) 0.0016(11) -0.0151(12) C11 0.0541(15) 0.0567(15) 0.0363(12) -0.0166(10) 0.0152(11) -0.0174(12) C12 0.0383(12) 0.0441(12) 0.0390(11) -0.0112(9) 0.0092(9) -0.0109(10) C13 0.0479(14) 0.0562(14) 0.0454(13) -0.0246(11) -0.0041(11) -0.0109(11) C14 0.0361(12) 0.0409(12) 0.0498(13) -0.0123(10) -0.0005(10) -0.0140(9) S1 0.0324(3) 0.0365(3) 0.0331(3) -0.0071(2) 0.0048(2) -0.0104(2) O2 0.0366(9) 0.0611(10) 0.0467(9) -0.0084(8) 0.0110(7) -0.0176(8) O3 0.0691(12) 0.0573(11) 0.0513(10) -0.0222(8) 0.0035(9) -0.0280(9) O4 0.0413(9) 0.0498(9) 0.0425(9) 0.0042(7) 0.0055(7) -0.0065(7) C15 0.0387(13) 0.0409(12) 0.0450(12) -0.0049(10) 0.0070(10) -0.0115(10) F1 0.0706(11) 0.0504(9) 0.0642(10) 0.0157(7) 0.0078(8) -0.0058(8) F2 0.0865(13) 0.0593(10) 0.0795(11) -0.0392(9) 0.0191(9) -0.0181(9) F3 0.0336(8) 0.0634(10) 0.0968(13) 0.0097(9) 0.0119(8) -0.0051(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 N1 C2 1.343(3) . ? N1 C5 1.371(3) . ? N1 C14 1.478(3) . ? C2 N3 1.345(3) . ? C2 C6 1.497(3) . ? N3 C4 1.359(3) . ? N3 C13 1.474(3) . ? C4 C5 1.350(4) . ? C4 H4 0.9400 . ? C5 H5 0.9400 . ? C6 O1 1.207(3) . ? C6 C7 1.478(3) . ? C7 C8 1.389(3) . ? C7 C12 1.401(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9400 . ? C9 C10 1.389(4) . ? C9 H9 0.9400 . ? C10 C11 1.379(4) . ? C10 H10 0.9400 . ? C11 C12 1.374(3) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? S1 O3 1.4347(17) . ? S1 O4 1.4356(16) . ? S1 O2 1.4372(17) . ? S1 C15 1.817(2) . ? C15 F2 1.323(3) . ? C15 F1 1.326(3) . ? C15 F3 1.329(3) . ? 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 109.00(18) . . ? C2 N1 C14 128.24(18) . . ? C5 N1 C14 122.41(19) . . ? N1 C2 N3 107.25(18) . . ? N1 C2 C6 128.57(18) . . ? N3 C2 C6 124.10(19) . . ? C2 N3 C4 109.04(19) . . ? C2 N3 C13 127.41(19) . . ? C4 N3 C13 123.55(19) . . ? C5 C4 N3 107.72(19) . . ? C5 C4 H4 126.1 . . ? N3 C4 H4 126.1 . . ? C4 C5 N1 107.0(2) . . ? C4 C5 H5 126.5 . . ? N1 C5 H5 126.5 . . ? O1 C6 C7 122.72(19) . . ? O1 C6 C2 118.25(19) . . ? C7 C6 C2 119.02(18) . . ? C8 C7 C12 119.5(2) . . ? C8 C7 C6 122.49(18) . . ? C12 C7 C6 117.9(2) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 120.1(2) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 S1 O4 114.97(11) . . ? O3 S1 O2 114.45(11) . . ? O4 S1 O2 115.50(10) . . ? O3 S1 C15 103.46(11) . . ? O4 S1 C15 103.45(10) . . ? O2 S1 C15 102.59(10) . . ? F2 C15 F1 107.5(2) . . ? F2 C15 F3 106.56(19) . . ? F1 C15 F3 107.6(2) . . ? F2 C15 S1 111.74(17) . . ? F1 C15 S1 111.41(16) . . ? F3 C15 S1 111.76(16) . . ? 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 N3 0.3(2) . . . . ? C14 N1 C2 N3 -172.90(19) . . . . ? C5 N1 C2 C6 177.0(2) . . . . ? C14 N1 C2 C6 3.8(3) . . . . ? N1 C2 N3 C4 -0.9(2) . . . . ? C6 C2 N3 C4 -177.74(19) . . . . ? N1 C2 N3 C13 178.64(19) . . . . ? C6 C2 N3 C13 1.8(3) . . . . ? C2 N3 C4 C5 1.1(2) . . . . ? C13 N3 C4 C5 -178.4(2) . . . . ? N3 C4 C5 N1 -1.0(2) . . . . ? C2 N1 C5 C4 0.4(2) . . . . ? C14 N1 C5 C4 174.07(19) . . . . ? N1 C2 C6 O1 -146.3(2) . . . . ? N3 C2 C6 O1 29.8(3) . . . . ? N1 C2 C6 C7 34.9(3) . . . . ? N3 C2 C6 C7 -148.9(2) . . . . ? O1 C6 C7 C8 -142.7(2) . . . . ? C2 C6 C7 C8 36.0(3) . . . . ? O1 C6 C7 C12 34.0(3) . . . . ? C2 C6 C7 C12 -147.2(2) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? C6 C7 C8 C9 176.8(2) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C10 C11 C12 C7 0.9(4) . . . . ? C8 C7 C12 C11 -0.9(3) . . . . ? C6 C7 C12 C11 -177.7(2) . . . . ? O3 S1 C15 F2 -179.39(16) . . . . ? O4 S1 C15 F2 -59.17(19) . . . . ? O2 S1 C15 F2 61.30(18) . . . . ? O3 S1 C15 F1 60.36(19) . . . . ? O4 S1 C15 F1 -179.41(17) . . . . ? O2 S1 C15 F1 -58.95(19) . . . . ? O3 S1 C15 F3 -60.08(19) . . . . ? O4 S1 C15 F3 60.14(19) . . . . ? O2 S1 C15 F3 -179.39(16) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 66.67 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.260 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.066 data_stu6327 _database_code_depnum_ccdc_archive 'CCDC 919090' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 F3 N2 O4 S' _chemical_formula_weight 378.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.6013(1) _cell_length_b 7.0186(1) _cell_length_c 25.4572(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.806(1) _cell_angle_gamma 90.00 _cell_volume 1713.44(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2871 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5317 _exptl_absorpt_correction_T_max 0.8617 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11633 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.61 _diffrn_reflns_theta_max 66.45 _reflns_number_total 2930 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+1.0085P] 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 2930 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.9094(2) 0.0478(3) 0.37594(8) 0.0376(5) Uani 1 1 d . . . N2 N 0.86084(19) 0.0286(3) 0.42452(7) 0.0416(4) Uani 1 1 d . . . C3 C 0.9134(2) -0.1352(4) 0.44660(10) 0.0481(6) Uani 1 1 d . . . H3 H 0.8955 -0.1828 0.4801 0.058 Uiso 1 1 calc R . . C4 C 0.9950(3) -0.2158(3) 0.41160(10) 0.0483(6) Uani 1 1 d . . . H4 H 1.0453 -0.3299 0.4163 0.058 Uiso 1 1 calc R . . N5 N 0.99221(19) -0.1032(3) 0.36807(7) 0.0418(4) Uani 1 1 d . . . C6 C 0.7707(3) 0.1565(4) 0.45345(10) 0.0614(7) Uani 1 1 d . . . H6A H 0.8148 0.2803 0.4574 0.092 Uiso 1 1 calc R . . H6B H 0.7561 0.1033 0.4879 0.092 Uiso 1 1 calc R . . H6C H 0.6816 0.1702 0.4342 0.092 Uiso 1 1 calc R . . C7 C 1.0784(3) -0.1422(4) 0.32328(11) 0.0579(7) Uani 1 1 d . . . H7A H 1.0190 -0.1543 0.2915 0.087 Uiso 1 1 calc R . . H7B H 1.1295 -0.2599 0.3295 0.087 Uiso 1 1 calc R . . H7C H 1.1435 -0.0383 0.3192 0.087 Uiso 1 1 calc R . . C8 C 0.8835(2) 0.2021(3) 0.33608(9) 0.0419(5) Uani 1 1 d . . . O9 O 0.9365(2) 0.1837(3) 0.29444(7) 0.0636(5) Uani 1 1 d . . . C10 C 0.7948(2) 0.3706(3) 0.34824(9) 0.0427(5) Uani 1 1 d . . . H10A H 0.8367 0.4383 0.3787 0.051 Uiso 1 1 calc R . . H10B H 0.7022 0.3264 0.3574 0.051 Uiso 1 1 calc R . . C11 C 0.7796(3) 0.5070(3) 0.30180(9) 0.0486(6) Uani 1 1 d . . . H11A H 0.8731 0.5468 0.2925 0.058 Uiso 1 1 calc R . . H11B H 0.7378 0.4371 0.2717 0.058 Uiso 1 1 calc R . . C12 C 0.6933(2) 0.6844(3) 0.30990(9) 0.0446(6) Uani 1 1 d . . . C13 C 0.6167(3) 0.7155(4) 0.35345(11) 0.0557(6) Uani 1 1 d . . . H13 H 0.6219 0.6270 0.3812 0.067 Uiso 1 1 calc R . . C14 C 0.5317(3) 0.8753(4) 0.35727(13) 0.0647(7) Uani 1 1 d . . . H14 H 0.4800 0.8936 0.3873 0.078 Uiso 1 1 calc R . . C15 C 0.5234(3) 1.0068(4) 0.31689(12) 0.0641(8) Uani 1 1 d . . . H15 H 0.4650 1.1137 0.3190 0.077 Uiso 1 1 calc R . . C16 C 0.6012(3) 0.9799(4) 0.27380(12) 0.0603(7) Uani 1 1 d . . . H16 H 0.5971 1.0704 0.2465 0.072 Uiso 1 1 calc R . . C17 C 0.6859(3) 0.8206(4) 0.26988(10) 0.0511(6) Uani 1 1 d . . . H17 H 0.7387 0.8044 0.2401 0.061 Uiso 1 1 calc R . . S1 S 1.21043(6) 0.28932(9) 0.41438(2) 0.0484(2) Uani 1 1 d . . . O1 O 1.2170(3) 0.3468(5) 0.36185(9) 0.1079(9) Uani 1 1 d . . . O2 O 1.09061(18) 0.3575(3) 0.43988(9) 0.0674(6) Uani 1 1 d . . . O3 O 1.2414(2) 0.0953(3) 0.42635(9) 0.0727(6) Uani 1 1 d . . . C100 C 1.3516(3) 0.4156(4) 0.44892(12) 0.0607(7) Uani 1 1 d . . . F1 F 1.3549(2) 0.3769(4) 0.49984(8) 0.1106(8) Uani 1 1 d . . . F2 F 1.47328(17) 0.3689(3) 0.43054(11) 0.1024(7) Uani 1 1 d . . . F3 F 1.3390(2) 0.6026(3) 0.44368(10) 0.0931(7) 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 0.0377(11) 0.0352(11) 0.0396(11) 0.0008(9) 0.0012(8) -0.0015(9) N2 0.0409(10) 0.0425(11) 0.0416(10) 0.0059(8) 0.0049(8) 0.0015(8) C3 0.0480(13) 0.0462(14) 0.0497(13) 0.0163(11) -0.0002(10) -0.0043(11) C4 0.0490(13) 0.0364(13) 0.0586(15) 0.0071(11) -0.0061(11) -0.0008(10) N5 0.0428(10) 0.0368(10) 0.0456(10) -0.0018(8) 0.0000(8) -0.0007(8) C6 0.0660(16) 0.0710(19) 0.0489(14) 0.0106(13) 0.0209(12) 0.0206(14) C7 0.0665(16) 0.0524(15) 0.0555(15) -0.0098(12) 0.0114(12) 0.0123(13) C8 0.0476(12) 0.0393(13) 0.0388(12) 0.0037(9) 0.0016(9) -0.0025(10) O9 0.0865(13) 0.0601(12) 0.0456(10) 0.0124(8) 0.0177(9) 0.0163(10) C10 0.0477(12) 0.0374(12) 0.0425(12) 0.0035(9) -0.0015(9) -0.0012(10) C11 0.0592(14) 0.0399(13) 0.0465(13) 0.0070(10) 0.0003(11) 0.0005(11) C12 0.0490(13) 0.0371(12) 0.0465(13) 0.0052(10) -0.0099(10) -0.0026(10) C13 0.0628(15) 0.0453(15) 0.0586(16) 0.0081(12) 0.0001(12) 0.0042(12) C14 0.0633(16) 0.0570(17) 0.0736(18) 0.0002(14) 0.0020(13) 0.0087(14) C15 0.0591(16) 0.0481(16) 0.083(2) 0.0017(14) -0.0151(14) 0.0090(13) C16 0.0657(16) 0.0428(14) 0.0697(17) 0.0129(13) -0.0238(14) -0.0025(12) C17 0.0577(14) 0.0434(14) 0.0507(14) 0.0061(11) -0.0113(11) -0.0069(11) S1 0.0506(4) 0.0443(4) 0.0499(4) 0.0028(2) -0.0022(3) -0.0054(3) O1 0.144(2) 0.129(2) 0.0491(13) 0.0127(13) -0.0049(13) -0.030(2) O2 0.0423(9) 0.0606(12) 0.0997(15) 0.0158(11) 0.0071(9) 0.0014(9) O3 0.0736(13) 0.0414(11) 0.1027(16) -0.0032(10) 0.0011(11) -0.0005(9) C100 0.0475(14) 0.0556(17) 0.079(2) -0.0045(14) 0.0074(13) -0.0057(12) F1 0.1056(16) 0.151(2) 0.0724(13) -0.0008(13) -0.0274(11) -0.0406(15) F2 0.0409(9) 0.0898(14) 0.178(2) -0.0087(14) 0.0225(11) -0.0004(9) F3 0.0762(12) 0.0515(11) 0.153(2) -0.0204(11) 0.0164(12) -0.0169(9) _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 N5 1.346(3) . ? C1 N2 1.349(3) . ? C1 C8 1.496(3) . ? N2 C3 1.366(3) . ? N2 C6 1.470(3) . ? C3 C4 1.340(4) . ? C3 H3 0.9400 . ? C4 N5 1.360(3) . ? C4 H4 0.9400 . ? N5 C7 1.467(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 O9 1.205(3) . ? C8 C10 1.499(3) . ? C10 C11 1.523(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C12 1.515(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.377(4) . ? C12 C17 1.396(3) . ? C13 C14 1.394(4) . ? C13 H13 0.9400 . ? C14 C15 1.381(4) . ? C14 H14 0.9400 . ? C15 C16 1.370(4) . ? C15 H15 0.9400 . ? C16 C17 1.389(4) . ? C16 H16 0.9400 . ? C17 H17 0.9400 . ? S1 O1 1.401(2) . ? S1 O3 1.423(2) . ? S1 O2 1.431(2) . ? S1 C100 1.811(3) . ? C100 F2 1.320(3) . ? C100 F1 1.323(4) . ? C100 F3 1.324(3) . ? 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 N5 C1 N2 106.92(18) . . ? N5 C1 C8 123.3(2) . . ? N2 C1 C8 129.8(2) . . ? C1 N2 C3 108.91(19) . . ? C1 N2 C6 129.6(2) . . ? C3 N2 C6 121.5(2) . . ? C4 C3 N2 107.3(2) . . ? C4 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? C3 C4 N5 107.9(2) . . ? C3 C4 H4 126.0 . . ? N5 C4 H4 126.0 . . ? C1 N5 C4 108.9(2) . . ? C1 N5 C7 128.5(2) . . ? C4 N5 C7 122.4(2) . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N5 C7 H7A 109.5 . . ? N5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O9 C8 C1 117.1(2) . . ? O9 C8 C10 122.4(2) . . ? C1 C8 C10 120.54(19) . . ? C8 C10 C11 111.68(19) . . ? C8 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C8 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 116.3(2) . . ? C12 C11 H11A 108.2 . . ? C10 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? C10 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? C13 C12 C17 118.0(2) . . ? C13 C12 C11 123.8(2) . . ? C17 C12 C11 118.1(2) . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C12 120.5(3) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? O1 S1 O3 117.45(17) . . ? O1 S1 O2 114.31(17) . . ? O3 S1 O2 112.76(13) . . ? O1 S1 C100 104.75(16) . . ? O3 S1 C100 102.75(13) . . ? O2 S1 C100 102.44(13) . . ? F2 C100 F1 108.5(3) . . ? F2 C100 F3 106.8(2) . . ? F1 C100 F3 107.4(3) . . ? F2 C100 S1 111.2(2) . . ? F1 C100 S1 110.91(19) . . ? F3 C100 S1 111.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 N2 C3 -0.3(2) . . . . ? C8 C1 N2 C3 -179.7(2) . . . . ? N5 C1 N2 C6 177.6(2) . . . . ? C8 C1 N2 C6 -1.8(4) . . . . ? C1 N2 C3 C4 0.4(3) . . . . ? C6 N2 C3 C4 -177.6(2) . . . . ? N2 C3 C4 N5 -0.4(3) . . . . ? N2 C1 N5 C4 0.0(2) . . . . ? C8 C1 N5 C4 179.5(2) . . . . ? N2 C1 N5 C7 -174.9(2) . . . . ? C8 C1 N5 C7 4.5(4) . . . . ? C3 C4 N5 C1 0.2(3) . . . . ? C3 C4 N5 C7 175.6(2) . . . . ? N5 C1 C8 O9 2.7(3) . . . . ? N2 C1 C8 O9 -177.9(2) . . . . ? N5 C1 C8 C10 -177.4(2) . . . . ? N2 C1 C8 C10 1.9(3) . . . . ? O9 C8 C10 C11 1.2(3) . . . . ? C1 C8 C10 C11 -178.6(2) . . . . ? C8 C10 C11 C12 -179.25(19) . . . . ? C10 C11 C12 C13 -8.0(4) . . . . ? C10 C11 C12 C17 175.0(2) . . . . ? C17 C12 C13 C14 1.5(4) . . . . ? C11 C12 C13 C14 -175.6(2) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 -1.1(4) . . . . ? C14 C15 C16 C17 1.2(4) . . . . ? C15 C16 C17 C12 0.1(4) . . . . ? C13 C12 C17 C16 -1.4(4) . . . . ? C11 C12 C17 C16 175.8(2) . . . . ? O1 S1 C100 F2 -60.7(3) . . . . ? O3 S1 C100 F2 62.5(3) . . . . ? O2 S1 C100 F2 179.6(2) . . . . ? O1 S1 C100 F1 178.5(2) . . . . ? O3 S1 C100 F1 -58.3(2) . . . . ? O2 S1 C100 F1 58.9(2) . . . . ? O1 S1 C100 F3 58.5(3) . . . . ? O3 S1 C100 F3 -178.2(2) . . . . ? O2 S1 C100 F3 -61.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 66.45 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.390 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.048 #============================================================================= # end of cif data for "stu6327" #============================================================================= #============================================================================= # end of cif file #=============================================================================