# Electronic Supplementary Material (ESI) for CrystEngComm # 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_form_M _database_code_depnum_ccdc_archive 'CCDC 908169' #TrackingRef '15017_web_deposit_cif_file_0_AnnaHoser_1351508093.FABTform_M.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F N3 O2 S, C2 H6 O S' _chemical_formula_sum 'C16 H16 F N3 O3 S2' _chemical_formula_weight 381.44 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.726(3) _cell_length_b 5.9694(13) _cell_length_c 18.782(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.438(12) _cell_angle_gamma 90.00 _cell_volume 1637.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12666 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_av_sigmaI/netI 0.1091 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2881 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0766P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2881 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1257 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.86312(8) 0.6115(2) 0.10952(6) 0.0203(3) Uani 1 1 d . . . S2 S 0.89944(8) 0.2703(2) 0.55171(6) 0.0243(4) Uani 1 1 d . . . F1 F 0.8030(2) 0.0506(5) -0.20566(15) 0.0365(8) Uani 1 1 d . . . N3 N 0.9422(2) 0.9755(7) 0.15034(19) 0.0198(9) Uani 1 1 d . . . C9 C 0.8762(3) 0.8014(8) 0.2482(2) 0.0173(11) Uani 1 1 d . . . O2 O 0.9490(2) 1.1597(6) 0.27641(18) 0.0260(9) Uani 1 1 d . . . O1S O 0.8155(2) 0.3590(6) 0.50594(16) 0.0285(9) Uani 1 1 d . . . C13 C 0.8142(3) 0.6059(9) 0.3438(2) 0.0203(11) Uani 1 1 d . . . H13 H 0.7840 0.4791 0.3603 0.024 Uiso 1 1 calc R . . O1 O 0.8300(2) 0.7755(7) 0.46048(16) 0.0248(9) Uani 1 1 d . . . N1 N 0.9254(3) 0.7253(8) -0.0183(2) 0.0209(10) Uani 1 1 d . . . N2 N 0.9562(3) 0.9559(7) 0.07958(19) 0.0215(10) Uani 1 1 d . . . C14 C 0.8313(3) 0.6203(9) 0.2730(2) 0.0194(11) Uani 1 1 d . . . H14 H 0.8115 0.5023 0.2407 0.023 Uiso 1 1 calc R . . C12 C 0.8425(3) 0.7828(9) 0.3903(2) 0.0187(11) Uani 1 1 d . . . C8 C 0.8970(3) 0.8121(8) 0.1746(2) 0.0164(11) Uani 1 1 d . . . C4 C 0.8914(3) 0.5466(8) -0.0630(2) 0.0162(11) Uani 1 1 d . . . C5 C 0.8537(3) 0.3547(9) -0.0394(2) 0.0217(12) Uani 1 1 d . . . H5 H 0.8486 0.3369 0.0102 0.026 Uiso 1 1 calc R . . C11 C 0.8852(3) 0.9670(9) 0.3664(2) 0.0195(12) Uani 1 1 d . . . H11 H 0.9030 1.0874 0.3983 0.023 Uiso 1 1 calc R . . C3 C 0.8998(3) 0.5719(9) -0.1357(2) 0.0239(12) Uani 1 1 d . . . H3 H 0.9260 0.7045 -0.1522 0.029 Uiso 1 1 calc R . . C10 C 0.9023(3) 0.9771(9) 0.2958(2) 0.0204(11) Uani 1 1 d . . . C7 C 0.9174(3) 0.7727(9) 0.0510(2) 0.0196(11) Uani 1 1 d . . . C2S C 0.9408(3) 0.4982(9) 0.6082(3) 0.0282(13) Uani 1 1 d . . . H23S H 0.9642 0.6160 0.5791 0.042 Uiso 1 1 calc R . . H21S H 0.9902 0.4456 0.6443 0.042 Uiso 1 1 calc R . . H22S H 0.8908 0.5583 0.6321 0.042 Uiso 1 1 calc R . . C6 C 0.8229(3) 0.1864(9) -0.0875(2) 0.0221(12) Uani 1 1 d . . . H6 H 0.7963 0.0534 -0.0717 0.027 Uiso 1 1 calc R . . C2 C 0.8702(3) 0.4055(9) -0.1833(2) 0.0239(12) Uani 1 1 d . . . H2 H 0.8763 0.4207 -0.2328 0.029 Uiso 1 1 calc R . . C1 C 0.8319(3) 0.2177(9) -0.1587(2) 0.0251(12) Uani 1 1 d . . . C1S C 0.8569(3) 0.1039(9) 0.6173(3) 0.0299(13) Uani 1 1 d . . . H12S H 0.8144 0.1925 0.6420 0.045 Uiso 1 1 calc R . . H13S H 0.9079 0.0524 0.6522 0.045 Uiso 1 1 calc R . . H11S H 0.8246 -0.0259 0.5942 0.045 Uiso 1 1 calc R . . H1N H 0.955(3) 0.824(8) -0.039(3) 0.023(15) Uiso 1 1 d . . . H2O H 0.972(4) 1.144(10) 0.237(3) 0.045(19) Uiso 1 1 d . . . H1O H 0.822(4) 0.625(12) 0.470(3) 0.08(2) Uiso 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 S1 0.0197(7) 0.0277(8) 0.0129(6) -0.0009(6) -0.0004(5) -0.0034(6) S2 0.0215(7) 0.0314(9) 0.0190(7) -0.0018(6) -0.0008(5) -0.0018(6) F1 0.0432(19) 0.035(2) 0.0286(17) -0.0095(15) -0.0060(14) -0.0071(15) N3 0.017(2) 0.025(3) 0.017(2) 0.0010(18) 0.0020(16) 0.0012(19) C9 0.013(2) 0.028(3) 0.011(2) 0.001(2) 0.0008(18) 0.002(2) O2 0.032(2) 0.028(2) 0.0184(19) -0.0018(16) 0.0055(16) -0.0068(17) O1S 0.030(2) 0.037(2) 0.0159(17) 0.0060(16) -0.0095(14) -0.0022(17) C13 0.018(3) 0.026(3) 0.016(2) 0.001(2) -0.0016(19) 0.002(2) O1 0.030(2) 0.031(2) 0.0132(18) -0.0008(16) 0.0033(14) -0.0011(18) N1 0.021(2) 0.031(3) 0.011(2) -0.0021(19) 0.0032(17) -0.008(2) N2 0.022(2) 0.034(3) 0.0078(19) 0.0020(18) -0.0003(16) 0.002(2) C14 0.014(2) 0.025(3) 0.019(2) -0.004(2) 0.0004(19) 0.000(2) C12 0.016(2) 0.029(3) 0.011(2) 0.000(2) 0.0011(18) 0.001(2) C8 0.012(2) 0.019(3) 0.018(2) 0.001(2) -0.0016(19) 0.001(2) C4 0.012(2) 0.024(3) 0.012(2) 0.000(2) 0.0004(18) 0.006(2) C5 0.019(3) 0.030(3) 0.016(2) 0.001(2) 0.0031(19) 0.003(2) C11 0.018(3) 0.031(3) 0.009(2) 0.002(2) -0.0018(18) -0.002(2) C3 0.020(3) 0.034(4) 0.017(3) 0.005(2) -0.001(2) 0.001(2) C10 0.012(2) 0.026(3) 0.023(3) 0.001(2) 0.0007(19) 0.000(2) C7 0.014(2) 0.029(3) 0.014(2) 0.002(2) -0.0048(18) -0.003(2) C2S 0.028(3) 0.026(3) 0.028(3) 0.003(2) -0.007(2) -0.004(2) C6 0.019(3) 0.023(3) 0.024(3) 0.000(2) -0.001(2) 0.002(2) C2 0.023(3) 0.037(3) 0.011(2) -0.002(2) -0.0030(19) -0.004(3) C1 0.022(3) 0.033(3) 0.019(3) -0.007(2) -0.002(2) -0.002(2) C1S 0.029(3) 0.031(3) 0.027(3) 0.008(3) -0.011(2) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.732(5) . ? S1 C8 1.737(5) . ? S2 O1S 1.508(3) . ? S2 C1S 1.760(5) . ? S2 C2S 1.783(5) . ? F1 C1 1.363(5) . ? N3 C8 1.296(6) . ? N3 N2 1.376(5) . ? C9 C14 1.379(7) . ? C9 C10 1.399(7) . ? C9 C8 1.457(6) . ? O2 C10 1.363(6) . ? C13 C14 1.389(6) . ? C13 C12 1.399(7) . ? O1 C12 1.355(5) . ? N1 C7 1.352(6) . ? N1 C4 1.409(6) . ? N2 C7 1.315(6) . ? C12 C11 1.371(7) . ? C4 C5 1.371(7) . ? C4 C3 1.396(6) . ? C5 C6 1.388(7) . ? C11 C10 1.383(6) . ? C3 C2 1.369(7) . ? C6 C1 1.372(7) . ? C2 C1 1.362(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 S1 C8 87.1(2) . . ? O1S S2 C1S 104.9(2) . . ? O1S S2 C2S 105.3(2) . . ? C1S S2 C2S 98.0(2) . . ? C8 N3 N2 115.0(4) . . ? C14 C9 C10 118.5(4) . . ? C14 C9 C8 121.6(4) . . ? C10 C9 C8 120.0(4) . . ? C14 C13 C12 118.4(5) . . ? C7 N1 C4 131.6(4) . . ? C7 N2 N3 110.7(4) . . ? C9 C14 C13 121.7(5) . . ? O1 C12 C11 118.0(4) . . ? O1 C12 C13 121.1(5) . . ? C11 C12 C13 120.9(4) . . ? N3 C8 C9 123.2(4) . . ? N3 C8 S1 112.7(3) . . ? C9 C8 S1 124.2(4) . . ? C5 C4 C3 119.9(5) . . ? C5 C4 N1 124.5(4) . . ? C3 C4 N1 115.6(4) . . ? C4 C5 C6 120.3(4) . . ? C12 C11 C10 119.8(5) . . ? C2 C3 C4 119.9(5) . . ? O2 C10 C11 116.8(4) . . ? O2 C10 C9 122.4(4) . . ? C11 C10 C9 120.7(5) . . ? N2 C7 N1 118.7(4) . . ? N2 C7 S1 114.5(3) . . ? N1 C7 S1 126.8(4) . . ? C1 C6 C5 118.1(5) . . ? C1 C2 C3 119.1(5) . . ? C2 C1 F1 119.4(4) . . ? C2 C1 C6 122.6(5) . . ? F1 C1 C6 118.0(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 C8 N3 N2 C7 1.5(5) . . . . ? C10 C9 C14 C13 -1.9(7) . . . . ? C8 C9 C14 C13 177.7(4) . . . . ? C12 C13 C14 C9 1.0(7) . . . . ? C14 C13 C12 O1 -178.2(4) . . . . ? C14 C13 C12 C11 0.7(7) . . . . ? N2 N3 C8 C9 179.4(4) . . . . ? N2 N3 C8 S1 -1.4(5) . . . . ? C14 C9 C8 N3 -177.2(4) . . . . ? C10 C9 C8 N3 2.4(7) . . . . ? C14 C9 C8 S1 3.7(6) . . . . ? C10 C9 C8 S1 -176.7(3) . . . . ? C7 S1 C8 N3 0.7(3) . . . . ? C7 S1 C8 C9 179.9(4) . . . . ? C7 N1 C4 C5 -12.0(8) . . . . ? C7 N1 C4 C3 169.3(5) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? N1 C4 C5 C6 -179.3(4) . . . . ? O1 C12 C11 C10 177.6(4) . . . . ? C13 C12 C11 C10 -1.3(7) . . . . ? C5 C4 C3 C2 0.1(7) . . . . ? N1 C4 C3 C2 178.8(4) . . . . ? C12 C11 C10 O2 -176.8(4) . . . . ? C12 C11 C10 C9 0.3(7) . . . . ? C14 C9 C10 O2 178.3(4) . . . . ? C8 C9 C10 O2 -1.4(7) . . . . ? C14 C9 C10 C11 1.3(7) . . . . ? C8 C9 C10 C11 -178.3(4) . . . . ? N3 N2 C7 N1 -179.2(4) . . . . ? N3 N2 C7 S1 -0.9(5) . . . . ? C4 N1 C7 N2 -179.3(4) . . . . ? C4 N1 C7 S1 2.7(7) . . . . ? C8 S1 C7 N2 0.1(4) . . . . ? C8 S1 C7 N1 178.3(4) . . . . ? C4 C5 C6 C1 0.4(7) . . . . ? C4 C3 C2 C1 0.7(7) . . . . ? C3 C2 C1 F1 -179.5(4) . . . . ? C3 C2 C1 C6 -1.0(8) . . . . ? C5 C6 C1 C2 0.5(7) . . . . ? C5 C6 C1 F1 179.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O N3 0.86(5) 1.92(6) 2.601(5) 135(5) . O1 H1O O1S 0.92(7) 1.74(7) 2.647(5) 168(6) . N1 H1N N2 0.86(5) 2.06(5) 2.918(6) 171(4) 3_775 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.347 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.092 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 908170' #TrackingRef '15018_web_deposit_cif_file_1_AnnaHoser_1351508093.FABTform_T.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 F N3 O3 S2' _chemical_formula_weight 381.44 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4038(4) _cell_length_b 10.2494(6) _cell_length_c 13.1644(9) _cell_angle_alpha 77.410(5) _cell_angle_beta 86.768(5) _cell_angle_gamma 82.386(5) _cell_volume 835.50(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10808 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2949 _reflns_number_gt 2074 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0451P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2949 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 H1N H 0.162(4) 0.084(3) 0.983(2) 0.028(8) Uiso 1 1 d . . . H2O H -0.194(5) -0.170(3) 0.718(2) 0.046(11) Uiso 1 1 d . . . H1O H -0.039(5) -0.279(3) 0.341(2) 0.055(10) Uiso 1 1 d . . . S1 S 0.33382(9) 0.00848(6) 0.74641(5) 0.01609(17) Uani 1 1 d . . . S2 S 0.72924(11) 0.50582(7) 1.34089(5) 0.0280(2) Uani 1 1 d . . . F1 F 0.8581(2) 0.39603(15) 0.98340(11) 0.0313(4) Uani 1 1 d . . . N3 N -0.0018(3) -0.10325(19) 0.79722(15) 0.0168(5) Uani 1 1 d . . . O2 O -0.2260(3) -0.18987(18) 0.67072(14) 0.0213(4) Uani 1 1 d . . . O1 O 0.0878(3) -0.25366(18) 0.34711(13) 0.0239(4) Uani 1 1 d . . . N2 N 0.0285(3) -0.04343(19) 0.87850(15) 0.0170(5) Uani 1 1 d . . . N1 N 0.2423(3) 0.0883(2) 0.93429(17) 0.0175(5) Uani 1 1 d . . . C14 C 0.2990(4) -0.1321(2) 0.55359(18) 0.0166(5) Uani 1 1 d . . . H14 H 0.4256 -0.1012 0.5678 0.020 Uiso 1 1 calc R . . C8 C 0.1405(4) -0.0857(2) 0.72201(18) 0.0145(5) Uani 1 1 d . . . C2 C 0.5303(4) 0.3164(2) 1.03331(19) 0.0211(6) Uani 1 1 d . . . H2 H 0.5134 0.3660 1.0869 0.025 Uiso 1 1 calc R . . C9 C 0.1300(4) -0.1340(2) 0.62644(17) 0.0138(5) Uani 1 1 d . . . C7 C 0.1966(4) 0.0201(2) 0.86268(17) 0.0136(5) Uani 1 1 d . . . O1S O 0.7262(3) 0.65585(17) 1.33001(14) 0.0344(5) Uani 1 1 d . . . C5 C 0.5827(4) 0.1741(2) 0.87486(18) 0.0175(6) Uani 1 1 d . . . H5 H 0.6004 0.1263 0.8201 0.021 Uiso 1 1 calc R . . C10 C -0.0552(4) -0.1806(2) 0.60382(18) 0.0153(5) Uani 1 1 d . . . C12 C 0.0971(4) -0.2159(2) 0.43953(18) 0.0171(6) Uani 1 1 d . . . C11 C -0.0711(4) -0.2198(2) 0.51017(18) 0.0167(5) Uani 1 1 d . . . H11 H -0.1978 -0.2493 0.4947 0.020 Uiso 1 1 calc R . . C4 C 0.4038(4) 0.1661(2) 0.93975(18) 0.0146(5) Uani 1 1 d . . . C3 C 0.3791(4) 0.2392(2) 1.01913(18) 0.0192(6) Uani 1 1 d . . . H3 H 0.2567 0.2352 1.0634 0.023 Uiso 1 1 calc R . . C6 C 0.7355(4) 0.2517(2) 0.88978(18) 0.0185(6) Uani 1 1 d . . . H6 H 0.8585 0.2569 0.8460 0.022 Uiso 1 1 calc R . . C13 C 0.2847(4) -0.1742(2) 0.46171(18) 0.0177(6) Uani 1 1 d . . . H13 H 0.4018 -0.1747 0.4141 0.021 Uiso 1 1 calc R . . C1 C 0.7062(4) 0.3204(2) 0.96859(19) 0.0197(6) Uani 1 1 d . . . C2S C 0.8161(5) 0.4754(3) 1.2172(2) 0.0383(8) Uani 1 1 d . . . H23S H 0.9664 0.4852 1.2066 0.058 Uiso 1 1 calc R . . H22S H 0.7361 0.5403 1.1629 0.058 Uiso 1 1 calc R . . H21S H 0.7940 0.3838 1.2135 0.058 Uiso 1 1 calc R . . C1S C 0.4612(4) 0.4817(3) 1.3372(3) 0.0449(8) Uani 1 1 d . . . H11S H 0.4506 0.3856 1.3441 0.067 Uiso 1 1 calc R . . H13S H 0.4027 0.5322 1.2708 0.067 Uiso 1 1 calc R . . H12S H 0.3819 0.5139 1.3947 0.067 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 0.0168(4) 0.0191(3) 0.0146(3) -0.0075(3) 0.0038(3) -0.0055(3) S2 0.0317(4) 0.0269(4) 0.0252(4) -0.0075(3) -0.0071(3) 0.0029(3) F1 0.0271(9) 0.0409(9) 0.0344(9) -0.0194(7) 0.0062(7) -0.0189(7) N3 0.0181(11) 0.0202(11) 0.0141(11) -0.0079(9) 0.0034(9) -0.0046(9) O2 0.0155(10) 0.0331(11) 0.0202(11) -0.0150(9) 0.0056(8) -0.0082(8) O1 0.0258(11) 0.0338(11) 0.0156(10) -0.0144(8) 0.0002(8) -0.0005(9) N2 0.0170(11) 0.0224(11) 0.0147(11) -0.0096(9) 0.0031(9) -0.0052(9) N1 0.0152(12) 0.0240(12) 0.0155(12) -0.0076(10) 0.0063(10) -0.0068(9) C14 0.0149(13) 0.0155(13) 0.0189(14) -0.0022(10) 0.0033(11) -0.0040(10) C8 0.0155(13) 0.0127(12) 0.0150(13) -0.0034(10) 0.0011(10) -0.0013(10) C2 0.0227(15) 0.0246(14) 0.0196(14) -0.0118(12) 0.0023(12) -0.0063(12) C9 0.0164(13) 0.0120(12) 0.0131(13) -0.0031(10) -0.0005(10) -0.0007(10) C7 0.0141(13) 0.0144(12) 0.0126(13) -0.0050(10) 0.0017(10) -0.0004(10) O1S 0.0326(11) 0.0288(11) 0.0488(13) -0.0226(9) -0.0115(9) -0.0005(8) C5 0.0193(14) 0.0199(14) 0.0145(13) -0.0075(11) 0.0014(11) -0.0016(11) C10 0.0139(13) 0.0148(13) 0.0167(13) -0.0044(10) 0.0020(10) 0.0007(10) C12 0.0218(14) 0.0136(13) 0.0155(13) -0.0050(10) -0.0003(11) 0.0023(10) C11 0.0163(13) 0.0171(13) 0.0184(14) -0.0071(11) -0.0026(11) -0.0017(10) C4 0.0167(13) 0.0131(12) 0.0144(13) -0.0033(10) -0.0016(10) -0.0016(10) C3 0.0199(14) 0.0210(14) 0.0170(14) -0.0049(11) 0.0042(11) -0.0039(11) C6 0.0145(13) 0.0238(14) 0.0168(14) -0.0036(11) 0.0022(11) -0.0030(11) C13 0.0166(13) 0.0194(13) 0.0159(13) -0.0041(11) 0.0056(10) 0.0000(10) C1 0.0182(14) 0.0203(14) 0.0230(14) -0.0053(11) -0.0017(11) -0.0094(11) C2S 0.062(2) 0.0237(16) 0.0313(17) -0.0108(13) 0.0084(15) -0.0085(14) C1S 0.0363(19) 0.0280(17) 0.067(2) -0.0016(16) -0.0055(16) -0.0065(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.740(2) . ? S1 C8 1.751(2) . ? S2 O1S 1.5106(18) . ? S2 C2S 1.770(3) . ? S2 C1S 1.771(3) . ? F1 C1 1.368(3) . ? N3 C8 1.307(3) . ? N3 N2 1.378(2) . ? O2 C10 1.365(3) . ? O1 C12 1.361(3) . ? N2 C7 1.314(3) . ? N1 C7 1.355(3) . ? N1 C4 1.401(3) . ? C14 C13 1.381(3) . ? C14 C9 1.404(3) . ? C8 C9 1.457(3) . ? C2 C3 1.373(3) . ? C2 C1 1.373(3) . ? C9 C10 1.405(3) . ? C5 C6 1.387(3) . ? C5 C4 1.390(3) . ? C10 C11 1.390(3) . ? C12 C11 1.382(3) . ? C12 C13 1.393(3) . ? C4 C3 1.403(3) . ? C6 C1 1.367(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 C7 S1 C8 87.12(11) . . ? O1S S2 C2S 104.77(12) . . ? O1S S2 C1S 104.81(12) . . ? C2S S2 C1S 99.17(16) . . ? C8 N3 N2 114.24(19) . . ? C7 N2 N3 111.93(18) . . ? C7 N1 C4 132.6(2) . . ? C13 C14 C9 121.2(2) . . ? N3 C8 C9 122.8(2) . . ? N3 C8 S1 112.66(17) . . ? C9 C8 S1 124.48(17) . . ? C3 C2 C1 118.8(2) . . ? C14 C9 C10 118.3(2) . . ? C14 C9 C8 121.8(2) . . ? C10 C9 C8 119.9(2) . . ? N2 C7 N1 118.7(2) . . ? N2 C7 S1 114.03(17) . . ? N1 C7 S1 127.28(18) . . ? C6 C5 C4 120.2(2) . . ? O2 C10 C11 116.9(2) . . ? O2 C10 C9 122.8(2) . . ? C11 C10 C9 120.4(2) . . ? O1 C12 C11 121.9(2) . . ? O1 C12 C13 117.6(2) . . ? C11 C12 C13 120.5(2) . . ? C12 C11 C10 120.1(2) . . ? C5 C4 N1 125.4(2) . . ? C5 C4 C3 119.0(2) . . ? N1 C4 C3 115.6(2) . . ? C2 C3 C4 120.6(2) . . ? C1 C6 C5 118.9(2) . . ? C14 C13 C12 119.4(2) . . ? C6 C1 F1 118.7(2) . . ? C6 C1 C2 122.5(2) . . ? F1 C1 C2 118.9(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 C8 N3 N2 C7 0.3(3) . . . . ? N2 N3 C8 C9 -176.26(19) . . . . ? N2 N3 C8 S1 0.6(2) . . . . ? C7 S1 C8 N3 -0.97(18) . . . . ? C7 S1 C8 C9 175.9(2) . . . . ? C13 C14 C9 C10 0.3(3) . . . . ? C13 C14 C9 C8 -178.0(2) . . . . ? N3 C8 C9 C14 -170.4(2) . . . . ? S1 C8 C9 C14 13.1(3) . . . . ? N3 C8 C9 C10 11.4(3) . . . . ? S1 C8 C9 C10 -165.08(17) . . . . ? N3 N2 C7 N1 177.52(19) . . . . ? N3 N2 C7 S1 -1.0(2) . . . . ? C4 N1 C7 N2 -178.9(2) . . . . ? C4 N1 C7 S1 -0.5(4) . . . . ? C8 S1 C7 N2 1.13(18) . . . . ? C8 S1 C7 N1 -177.3(2) . . . . ? C14 C9 C10 O2 178.2(2) . . . . ? C8 C9 C10 O2 -3.6(3) . . . . ? C14 C9 C10 C11 -1.8(3) . . . . ? C8 C9 C10 C11 176.4(2) . . . . ? O1 C12 C11 C10 179.9(2) . . . . ? C13 C12 C11 C10 0.7(3) . . . . ? O2 C10 C11 C12 -178.6(2) . . . . ? C9 C10 C11 C12 1.4(3) . . . . ? C6 C5 C4 N1 -178.0(2) . . . . ? C6 C5 C4 C3 1.0(3) . . . . ? C7 N1 C4 C5 -10.8(4) . . . . ? C7 N1 C4 C3 170.1(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C5 C4 C3 C2 -0.7(3) . . . . ? N1 C4 C3 C2 178.4(2) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C9 C14 C13 C12 1.8(3) . . . . ? O1 C12 C13 C14 178.5(2) . . . . ? C11 C12 C13 C14 -2.3(3) . . . . ? C5 C6 C1 F1 179.6(2) . . . . ? C5 C6 C1 C2 -0.4(4) . . . . ? C3 C2 C1 C6 0.8(4) . . . . ? C3 C2 C1 F1 -179.2(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 O2 H2O N3 0.75(3) 1.93(3) 2.622(3) 153(3) . O1 H1O O1S 0.90(3) 1.75(3) 2.644(3) 174(3) 1_444 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.350 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.057