# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_chaume_C15H16F3N3O8S _database_code_depnum_ccdc_archive 'CCDC 910329' #TrackingRef '2012_njc_chaume.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 F3 N3 O8 S' _chemical_formula_sum 'C15 H16 F3 N3 O8 S' _chemical_formula_weight 455.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.177(1) _cell_length_b 11.319(1) _cell_length_c 20.788(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1924.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 16146 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9207 _exptl_absorpt_correction_T_max 0.9757 _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18849 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5601 _reflns_number_gt 4878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'PLATON (Spek, 2009)' _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^)+(0.0342P)^2^+0.3983P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(6) _refine_ls_number_reflns 5601 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0791 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 S1 S 0.11828(5) 0.74563(3) 0.202368(16) 0.02451(8) Uani 1 1 d . . . F1 F 0.4784(2) 0.89629(13) 0.39844(7) 0.0669(4) Uani 1 1 d . . . F2 F 0.5501(2) 0.74312(13) 0.45156(5) 0.0616(4) Uani 1 1 d . . . F3 F 0.7029(2) 0.89742(14) 0.45267(7) 0.0735(5) Uani 1 1 d . . . O1 O -0.0888(2) 0.81235(13) 0.01585(7) 0.0545(4) Uani 1 1 d . . . O2 O 0.14197(16) 0.83037(11) 0.06570(6) 0.0361(3) Uani 1 1 d . . . O3 O 0.02734(16) 0.85251(10) 0.19260(6) 0.0324(3) Uani 1 1 d . . . O4 O 0.11663(16) 0.69027(11) 0.26436(5) 0.0321(3) Uani 1 1 d . . . O5 O 0.52956(18) 0.88708(10) 0.25846(6) 0.0373(3) Uani 1 1 d . . . O6 O 0.81877(18) 0.70788(12) 0.38063(7) 0.0449(4) Uani 1 1 d . . . O7 O 0.52655(16) 0.44803(10) 0.39383(5) 0.0295(3) Uani 1 1 d . . . O8 O 0.35791(15) 0.59236(11) 0.36041(6) 0.0326(3) Uani 1 1 d . . . N1 N 0.0157(2) 0.77687(12) 0.05345(6) 0.0303(3) Uani 1 1 d . . . N2 N 0.30529(18) 0.76852(14) 0.18412(7) 0.0308(3) Uani 1 1 d . . . H2N H 0.328(3) 0.818(2) 0.1538(12) 0.061(8) Uiso 1 1 d . . . N3 N 0.60155(18) 0.72265(11) 0.31205(6) 0.0256(3) Uani 1 1 d . . . C1 C 0.03535(19) 0.63894(13) 0.14814(7) 0.0226(3) Uani 1 1 d . . . C2 C 0.0031(2) 0.52681(14) 0.17270(8) 0.0264(3) Uani 1 1 d . . . H2 H 0.0332 0.5089 0.2158 0.032 Uiso 1 1 calc R . . C3 C -0.0722(2) 0.44065(15) 0.13538(9) 0.0328(4) Uani 1 1 d . . . H3 H -0.0928 0.3646 0.1529 0.039 Uiso 1 1 calc R . . C4 C -0.1171(3) 0.46560(16) 0.07263(9) 0.0354(4) Uani 1 1 d . . . H4 H -0.1675 0.4064 0.0470 0.042 Uiso 1 1 calc R . . C5 C -0.0885(2) 0.57715(16) 0.04717(8) 0.0316(4) Uani 1 1 d . . . H5 H -0.1208 0.5950 0.0044 0.038 Uiso 1 1 calc R . . C6 C -0.0130(2) 0.66171(14) 0.08442(7) 0.0256(3) Uani 1 1 d . . . C7 C 0.4417(2) 0.70272(14) 0.21162(7) 0.0263(3) Uani 1 1 d . . . H7 H 0.4005 0.6283 0.2319 0.032 Uiso 1 1 calc R . . C8 C 0.5257(2) 0.77969(13) 0.26264(7) 0.0265(3) Uani 1 1 d . . . C9 C 0.5657(3) 0.67273(17) 0.15856(9) 0.0364(4) Uani 1 1 d . . . H9A H 0.5124 0.6247 0.1254 0.055 Uiso 1 1 calc R . . H9B H 0.6571 0.6284 0.1772 0.055 Uiso 1 1 calc R . . H9C H 0.6068 0.7459 0.1393 0.055 Uiso 1 1 calc R . . C10 C 0.6065(3) 0.83139(18) 0.41521(9) 0.0416(4) Uani 1 1 d . . . C11 C 0.7021(2) 0.78743(15) 0.35725(8) 0.0301(4) Uani 1 1 d . . . H11 H 0.7572 0.8551 0.3352 0.036 Uiso 1 1 calc R . . C12 C 0.7987(2) 0.59485(15) 0.35065(9) 0.0314(4) Uani 1 1 d . . . H12A H 0.8086 0.5307 0.3828 0.038 Uiso 1 1 calc R . . H12B H 0.8825 0.5828 0.3169 0.038 Uiso 1 1 calc R . . C13 C 0.6278(2) 0.59617(13) 0.32131(7) 0.0253(3) Uani 1 1 d . . . H13 H 0.6305 0.5560 0.2785 0.030 Uiso 1 1 calc R . . C14 C 0.5001(2) 0.53743(13) 0.36361(7) 0.0247(3) Uani 1 1 d . . . C15 C 0.2232(2) 0.5387(2) 0.39490(10) 0.0424(5) Uani 1 1 d . . . H15A H 0.1827 0.4705 0.3707 0.064 Uiso 1 1 calc R . . H15B H 0.1350 0.5966 0.4000 0.064 Uiso 1 1 calc R . . H15C H 0.2608 0.5129 0.4374 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02723(17) 0.02509(17) 0.02121(15) -0.00077(14) -0.00041(14) -0.00074(17) F1 0.0686(10) 0.0651(9) 0.0669(8) -0.0159(7) 0.0004(7) 0.0335(8) F2 0.0822(10) 0.0665(8) 0.0362(6) 0.0003(6) 0.0047(6) -0.0107(8) F3 0.0806(11) 0.0782(10) 0.0617(8) -0.0425(8) -0.0095(8) -0.0162(9) O1 0.0704(11) 0.0418(8) 0.0513(8) 0.0116(6) -0.0304(8) -0.0008(8) O2 0.0356(7) 0.0370(7) 0.0356(6) 0.0073(5) 0.0029(5) -0.0067(6) O3 0.0365(7) 0.0256(6) 0.0351(6) -0.0045(5) -0.0006(5) 0.0046(5) O4 0.0360(6) 0.0386(6) 0.0217(5) 0.0027(4) -0.0011(5) -0.0064(6) O5 0.0506(8) 0.0203(6) 0.0411(7) 0.0029(5) -0.0125(6) -0.0013(6) O6 0.0414(8) 0.0369(7) 0.0565(8) -0.0139(6) -0.0239(7) 0.0107(6) O7 0.0364(7) 0.0255(6) 0.0265(5) 0.0026(4) 0.0011(5) 0.0019(5) O8 0.0257(6) 0.0347(6) 0.0375(6) 0.0054(5) -0.0005(5) 0.0030(5) N1 0.0401(8) 0.0290(7) 0.0217(6) 0.0000(5) -0.0016(6) 0.0027(6) N2 0.0261(7) 0.0346(8) 0.0319(7) 0.0115(6) -0.0056(5) -0.0058(6) N3 0.0301(7) 0.0187(6) 0.0280(6) -0.0012(4) -0.0058(5) -0.0009(5) C1 0.0190(7) 0.0241(7) 0.0246(7) -0.0019(6) -0.0002(6) 0.0015(6) C2 0.0245(8) 0.0263(8) 0.0284(7) 0.0016(6) 0.0004(6) 0.0012(7) C3 0.0347(9) 0.0236(8) 0.0399(9) -0.0009(7) 0.0020(7) -0.0019(7) C4 0.0381(10) 0.0289(8) 0.0392(9) -0.0100(7) -0.0031(8) -0.0031(8) C5 0.0337(9) 0.0340(9) 0.0270(8) -0.0064(6) -0.0025(7) 0.0016(7) C6 0.0281(8) 0.0251(7) 0.0237(7) -0.0018(6) -0.0007(6) 0.0038(7) C7 0.0276(8) 0.0232(7) 0.0281(8) 0.0026(6) -0.0021(6) -0.0022(6) C8 0.0279(8) 0.0232(8) 0.0286(7) -0.0002(6) -0.0004(6) 0.0004(6) C9 0.0425(11) 0.0328(9) 0.0338(9) -0.0017(7) 0.0023(8) 0.0073(8) C10 0.0481(12) 0.0368(10) 0.0401(10) -0.0109(8) -0.0087(9) 0.0003(10) C11 0.0286(8) 0.0256(8) 0.0360(9) -0.0028(7) -0.0112(7) -0.0014(7) C12 0.0281(9) 0.0260(8) 0.0402(9) 0.0039(7) 0.0000(7) 0.0017(7) C13 0.0286(8) 0.0197(7) 0.0275(7) 0.0012(6) -0.0009(7) 0.0025(7) C14 0.0266(8) 0.0237(7) 0.0237(7) -0.0028(6) -0.0042(6) 0.0007(7) C15 0.0295(9) 0.0548(13) 0.0429(10) 0.0025(10) 0.0054(8) -0.0023(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 S1 O4 1.4330(11) . ? S1 O3 1.4345(12) . ? S1 N2 1.5968(16) . ? S1 C1 1.7858(15) . ? F1 C10 1.327(3) . ? F2 C10 1.335(2) . ? F3 C10 1.337(2) . ? O1 N1 1.226(2) . ? O2 N1 1.224(2) . ? O5 C8 1.2191(18) . ? O6 C11 1.399(2) . ? O6 C12 1.432(2) . ? O7 C14 1.2105(19) . ? O8 C14 1.320(2) . ? O8 C15 1.447(2) . ? N1 C6 1.473(2) . ? N2 C7 1.458(2) . ? N2 H2N 0.86(3) . ? N3 C8 1.363(2) . ? N3 C11 1.448(2) . ? N3 C13 1.4603(19) . ? C1 C2 1.393(2) . ? C1 C6 1.406(2) . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.377(2) . ? C5 H5 0.9500 . ? C7 C8 1.535(2) . ? C7 C9 1.536(2) . ? C7 H7 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.520(3) . ? C11 H11 1.0000 . ? C12 C13 1.525(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.519(2) . ? C13 H13 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 O4 S1 O3 119.42(7) . . ? O4 S1 N2 107.08(8) . . ? O3 S1 N2 109.03(8) . . ? O4 S1 C1 105.57(7) . . ? O3 S1 C1 106.51(7) . . ? N2 S1 C1 108.87(8) . . ? C11 O6 C12 110.23(13) . . ? C14 O8 C15 116.59(14) . . ? O2 N1 O1 123.97(15) . . ? O2 N1 C6 118.78(14) . . ? O1 N1 C6 117.24(15) . . ? C7 N2 S1 123.82(12) . . ? C7 N2 H2N 117.0(18) . . ? S1 N2 H2N 119.0(18) . . ? C8 N3 C11 120.51(13) . . ? C8 N3 C13 129.10(13) . . ? C11 N3 C13 109.12(13) . . ? C2 C1 C6 117.33(14) . . ? C2 C1 S1 117.16(12) . . ? C6 C1 S1 125.27(12) . . ? C3 C2 C1 121.23(15) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 120.02(16) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.99(16) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.53(16) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 121.89(15) . . ? C5 C6 N1 116.15(14) . . ? C1 C6 N1 121.96(14) . . ? N2 C7 C8 108.87(13) . . ? N2 C7 C9 109.65(13) . . ? C8 C7 C9 109.03(14) . . ? N2 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C9 C7 H7 109.8 . . ? O5 C8 N3 120.96(15) . . ? O5 C8 C7 121.88(15) . . ? N3 C8 C7 117.11(13) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? F1 C10 F2 106.87(19) . . ? F1 C10 F3 108.02(17) . . ? F2 C10 F3 107.00(16) . . ? F1 C10 C11 112.30(16) . . ? F2 C10 C11 112.42(15) . . ? F3 C10 C11 109.98(18) . . ? O6 C11 N3 106.66(13) . . ? O6 C11 C10 106.62(15) . . ? N3 C11 C10 112.83(15) . . ? O6 C11 H11 110.2 . . ? N3 C11 H11 110.2 . . ? C10 C11 H11 110.2 . . ? O6 C12 C13 105.68(14) . . ? O6 C12 H12A 110.6 . . ? C13 C12 H12A 110.6 . . ? O6 C12 H12B 110.6 . . ? C13 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? N3 C13 C14 113.86(14) . . ? N3 C13 C12 101.36(13) . . ? C14 C13 C12 113.22(13) . . ? N3 C13 H13 109.4 . . ? C14 C13 H13 109.4 . . ? C12 C13 H13 109.4 . . ? O7 C14 O8 125.26(16) . . ? O7 C14 C13 122.93(15) . . ? O8 C14 C13 111.73(13) . . ? O8 C15 H15A 109.5 . . ? O8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.166 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.043 #===END