# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Timothy Norris' _publ_contact_author_address ; Chemical Research & Development Pfizer Global Research & Development Eastern Point Road Groton CT 06340 ; _publ_contact_author_email 'TIMOTHY NORRIS@GROTON.PFIZER.COM' _publ_section_title ; New hydroxy-pyrazoline intermediates, subtle regio-selectivity and relative reaction rates variation observed during acid catalyzed and neutral pyrazole cyclization ; loop_ _publ_author_name 'Timothy Norris' 'Roberto Colon-Cruz' 'David H.B. Ripin' data_f783 _database_code_depnum_ccdc_archive 'CCDC 263085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 F2 N3 O3 S' _chemical_formula_weight 367.37 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 P2(1)/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 10.5772(4) _cell_length_b 17.2951(7) _cell_length_c 9.3940(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.7810(10) _cell_angle_gamma 90.00 _cell_volume 1617.08(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.188 _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 298(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 'CCD area detector' _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 3360 _diffrn_reflns_av_R_equivalents 0.1021 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.44 _diffrn_reflns_theta_max 44.94 _reflns_number_total 1285 _reflns_number_gt 1150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0926P)^2^+0.1467P] 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 SHELXL _refine_ls_extinction_coef 0.0236(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1285 _refine_ls_number_parameters 231 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.001 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 -0.1411(3) -0.05586(18) -0.3895(4) 0.0423(10) Uani 1 1 d . . . C2 C -0.2015(4) -0.1093(2) -0.4798(4) 0.0420(11) Uani 1 1 d . . . C3 C -0.1336(4) -0.1866(2) -0.4510(4) 0.0506(12) Uani 1 1 d . . . H3A H -0.1163 -0.2052 -0.5389 0.080 Uiso 1 1 calc R . . H3B H -0.1864 -0.2240 -0.4205 0.080 Uiso 1 1 calc R . . C4 C -0.0021(4) -0.1682(2) -0.3216(4) 0.0409(11) Uani 1 1 d . . . N5 N -0.0229(3) -0.08566(17) -0.2914(4) 0.0410(10) Uani 1 1 d . . . C6 C 0.0591(4) -0.0406(2) -0.1783(4) 0.0369(11) Uani 1 1 d . . . C7 C 0.0339(4) 0.0380(2) -0.1661(4) 0.0414(11) Uani 1 1 d . . . H7 H -0.0453 0.0620 -0.2344 0.080 Uiso 1 1 calc R . . C8 C 0.1251(4) 0.0798(2) -0.0540(5) 0.0445(12) Uani 1 1 d . . . H8 H 0.1109 0.1339 -0.0429 0.080 Uiso 1 1 calc R . . C9 C 0.2385(4) 0.0432(2) 0.0438(4) 0.0392(11) Uani 1 1 d . . . C10 C 0.2515(4) -0.0351(3) 0.0266(4) 0.0441(11) Uani 1 1 d . . . H10 H 0.3275 -0.0608 0.0972 0.080 Uiso 1 1 calc R . . N11 N 0.1655(3) -0.07783(17) -0.0816(4) 0.0445(10) Uani 1 1 d . . . C12 C 0.1221(4) -0.1777(2) -0.3666(4) 0.0379(11) Uani 1 1 d . . . C13 C 0.1602(4) -0.1201(2) -0.4459(4) 0.0455(12) Uani 1 1 d . . . H13 H 0.1096 -0.0729 -0.4692 0.080 Uiso 1 1 calc R . . C14 C 0.2699(5) -0.1296(3) -0.4920(4) 0.0533(12) Uani 1 1 d . . . H14 H 0.2948 -0.0891 -0.5472 0.080 Uiso 1 1 calc R . . C15 C 0.3437(4) -0.1967(3) -0.4596(5) 0.0606(13) Uani 1 1 d . . . H15 H 0.4204 -0.2030 -0.4913 0.080 Uiso 1 1 calc R . . C16 C 0.3072(5) -0.2546(3) -0.3813(5) 0.0561(13) Uani 1 1 d . . . H16 H 0.3592 -0.3014 -0.3577 0.080 Uiso 1 1 calc R . . C17 C 0.1954(4) -0.2462(2) -0.3360(4) 0.0469(12) Uani 1 1 d . . . H17 H 0.1691 -0.2876 -0.2838 0.080 Uiso 1 1 calc R . . O18 O 0.0065(3) -0.21515(16) -0.1960(3) 0.0550(9) Uani 1 1 d D . . H18 H -0.054(3) -0.204(3) -0.164(5) 0.080 Uiso 1 1 d D . . C19 C -0.3326(4) -0.0908(3) -0.5983(5) 0.0555(13) Uani 1 1 d . . . H19 H -0.3718 -0.0457 -0.5704 0.080 Uiso 1 1 calc R . . F20 F -0.3153(3) -0.07983(19) -0.7320(3) 0.1081(12) Uani 1 1 d . . . F21 F -0.4167(2) -0.15109(16) -0.6199(3) 0.0915(10) Uani 1 1 d . . . S22 S 0.36482(10) 0.09377(6) 0.18241(11) 0.0494(6) Uani 1 1 d . . . O23 O 0.3090(3) 0.16326(14) 0.2169(3) 0.0624(10) Uani 1 1 d . . . O24 O 0.4303(3) 0.04123(16) 0.3030(3) 0.0675(10) Uani 1 1 d . . . C25 C 0.4784(5) 0.1188(3) 0.0928(5) 0.0834(16) Uani 1 1 d . . . H25A H 0.4341 0.1503 0.0061 0.080 Uiso 1 1 calc R . . H25B H 0.5122 0.0728 0.0612 0.080 Uiso 1 1 calc R . . H25C H 0.5517 0.1472 0.1617 0.080 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 0.037(2) 0.043(2) 0.042(2) 0.000(2) 0.0078(18) -0.003(2) C2 0.033(3) 0.048(3) 0.042(3) -0.005(3) 0.009(2) -0.007(3) C3 0.042(3) 0.043(3) 0.059(3) -0.006(2) 0.007(2) -0.001(2) C4 0.044(3) 0.031(3) 0.041(3) 0.001(2) 0.005(2) 0.000(2) N5 0.031(2) 0.037(2) 0.042(2) -0.0034(19) -0.003(2) 0.0047(18) C6 0.030(3) 0.042(3) 0.035(3) -0.004(2) 0.006(2) -0.008(3) C7 0.039(3) 0.035(3) 0.046(3) -0.001(2) 0.007(2) 0.003(2) C8 0.044(3) 0.036(2) 0.050(3) -0.006(2) 0.012(2) -0.003(2) C9 0.031(3) 0.042(3) 0.039(2) -0.006(2) 0.006(2) -0.002(2) C10 0.033(3) 0.050(3) 0.041(3) -0.004(2) 0.001(2) 0.001(2) N11 0.039(2) 0.042(2) 0.043(2) -0.0013(19) 0.001(2) 0.005(2) C12 0.036(3) 0.037(3) 0.036(2) 0.001(2) 0.005(2) -0.003(2) C13 0.041(3) 0.047(3) 0.046(3) 0.000(2) 0.011(2) 0.002(2) C14 0.056(3) 0.052(3) 0.049(3) -0.006(2) 0.014(2) -0.009(3) C15 0.046(3) 0.071(3) 0.059(3) -0.019(3) 0.010(3) -0.009(3) C16 0.041(3) 0.049(3) 0.066(3) -0.013(3) 0.002(3) 0.011(2) C17 0.045(3) 0.036(3) 0.048(3) -0.0020(19) 0.001(2) 0.003(2) O18 0.056(2) 0.0529(18) 0.063(2) 0.0090(16) 0.0297(16) 0.0014(16) C19 0.044(3) 0.066(3) 0.047(3) -0.008(2) 0.003(3) -0.008(3) F20 0.075(2) 0.191(3) 0.0469(18) 0.0201(18) 0.0060(16) 0.0031(19) F21 0.0492(17) 0.098(2) 0.101(2) -0.0064(16) -0.0080(15) -0.0241(17) S22 0.0396(9) 0.0576(9) 0.0475(9) -0.0126(6) 0.0100(7) -0.0066(6) O23 0.060(2) 0.0548(18) 0.0667(19) -0.0232(15) 0.0141(16) -0.0022(16) O24 0.0548(19) 0.074(2) 0.0555(18) 0.0008(17) -0.0053(15) 0.0034(16) C25 0.065(3) 0.118(4) 0.072(3) -0.038(3) 0.029(3) -0.039(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 N1 C2 1.271(4) . ? N1 N5 1.378(4) . ? C2 C19 1.490(5) . ? C2 C3 1.497(5) . ? C3 C4 1.539(5) . ? C4 O18 1.409(4) . ? C4 N5 1.486(5) . ? C4 C12 1.519(6) . ? N5 C6 1.366(4) . ? C6 N11 1.347(4) . ? C6 C7 1.397(5) . ? C7 C8 1.369(5) . ? C8 C9 1.392(5) . ? C9 C10 1.376(5) . ? C9 S22 1.752(4) . ? C10 N11 1.335(4) . ? C12 C13 1.383(5) . ? C12 C17 1.392(5) . ? C13 C14 1.379(5) . ? C14 C15 1.373(6) . ? C15 C16 1.374(6) . ? C16 C17 1.393(6) . ? C19 F21 1.340(5) . ? C19 F20 1.343(5) . ? S22 O23 1.424(3) . ? S22 O24 1.434(3) . ? S22 C25 1.739(4) . ? 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 N5 108.1(3) . . ? N1 C2 C19 118.2(4) . . ? N1 C2 C3 115.3(3) . . ? C19 C2 C3 126.5(4) . . ? C2 C3 C4 102.0(3) . . ? O18 C4 N5 111.4(3) . . ? O18 C4 C12 110.7(3) . . ? N5 C4 C12 110.8(3) . . ? O18 C4 C3 109.1(3) . . ? N5 C4 C3 101.3(3) . . ? C12 C4 C3 113.2(3) . . ? C6 N5 N1 120.0(3) . . ? C6 N5 C4 126.9(3) . . ? N1 N5 C4 113.0(3) . . ? N11 C6 N5 114.6(3) . . ? N11 C6 C7 123.3(3) . . ? N5 C6 C7 122.1(4) . . ? C8 C7 C6 118.2(3) . . ? C7 C8 C9 119.6(3) . . ? C10 C9 C8 117.9(3) . . ? C10 C9 S22 119.8(3) . . ? C8 C9 S22 122.2(3) . . ? N11 C10 C9 124.4(3) . . ? C10 N11 C6 116.6(3) . . ? C13 C12 C17 118.7(4) . . ? C13 C12 C4 120.6(3) . . ? C17 C12 C4 120.6(4) . . ? C14 C13 C12 120.8(4) . . ? C15 C14 C13 120.5(4) . . ? C16 C15 C14 119.6(4) . . ? C15 C16 C17 120.6(4) . . ? C12 C17 C16 119.8(4) . . ? F21 C19 F20 105.1(3) . . ? F21 C19 C2 110.4(3) . . ? F20 C19 C2 110.0(3) . . ? O23 S22 O24 118.82(17) . . ? O23 S22 C25 107.9(2) . . ? O24 S22 C25 108.2(2) . . ? O23 S22 C9 108.67(18) . . ? O24 S22 C9 108.25(18) . . ? C25 S22 C9 104.07(19) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 44.94 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.311 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.116 data_f596 _database_code_depnum_ccdc_archive 'CCDC 263086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F3 N3 O2 S' _chemical_formula_weight 367.35 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 C2/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 31.208(4) _cell_length_b 5.0510(10) _cell_length_c 21.756(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.080(10) _cell_angle_gamma 90.00 _cell_volume 3221.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5.998 _cell_measurement_theta_max 54.666 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 2.245 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker P4' _diffrn_measurement_method 'theta and 2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1679 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 49.99 _reflns_number_total 1639 _reflns_number_gt 1245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0609P)^2^+4.2154P] 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 SHELXL _refine_ls_extinction_coef 0.00052(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1639 _refine_ls_number_parameters 285 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.004 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 0.12380(12) 0.4532(8) 0.49292(17) 0.0417(10) Uani 1 1 d . . . N2 N 0.12326(13) 0.3935(8) 0.43149(17) 0.0480(11) Uani 1 1 d . . . C3 C 0.09029(16) 0.2176(10) 0.40923(18) 0.0520(14) Uani 1 1 d D . . C4 C 0.06977(16) 0.1609(12) 0.4555(2) 0.0598(15) Uani 1 1 d . . . H4A H 0.0461 0.0419 0.4509 0.080 Uiso 1 1 calc R . . C5 C 0.09106(15) 0.3136(10) 0.5087(2) 0.0436(13) Uani 1 1 d . . . C6 C 0.15726(14) 0.6401(9) 0.5292(2) 0.0378(12) Uani 1 1 d . . . N7 N 0.16382(14) 0.6567(9) 0.59159(19) 0.0596(13) Uani 1 1 d . . . C8 C 0.19543(17) 0.8278(12) 0.6266(2) 0.0584(15) Uani 1 1 d . . . H8A H 0.2002 0.8436 0.6710 0.080 Uiso 1 1 calc R . . C9 C 0.22111(14) 0.9810(9) 0.6007(2) 0.0365(12) Uani 1 1 d . . . C10 C 0.21305(18) 0.9604(10) 0.5349(2) 0.0566(14) Uani 1 1 d . . . H10A H 0.2295 1.0636 0.5154 0.080 Uiso 1 1 calc R . . C11 C 0.18051(18) 0.7862(11) 0.4979(2) 0.0597(16) Uani 1 1 d . . . H11D H 0.1745 0.7682 0.4531 0.080 Uiso 1 1 calc R . . S12 S 0.26348(4) 1.1937(2) 0.65098(6) 0.0456(5) Uani 1 1 d . . . O13 O 0.27701(12) 1.3662(7) 0.60864(15) 0.0661(11) Uani 1 1 d . . . O14 O 0.24764(11) 1.3075(7) 0.69937(15) 0.0608(10) Uani 1 1 d . . . C15 C 0.30840(16) 0.9798(11) 0.6914(2) 0.0642(16) Uani 1 1 d . . . H15A H 0.3200 0.9005 0.6601 0.080 Uiso 1 1 calc R . . H15B H 0.2976 0.8438 0.7132 0.080 Uiso 1 1 calc R . . H15C H 0.3323 1.0777 0.7230 0.080 Uiso 1 1 calc R . . C16 C 0.07898(17) 0.1065(12) 0.3423(2) 0.0670(17) Uani 1 1 d D . . F17 F 0.0559(8) 0.269(2) 0.2977(3) 0.107(4) Uani 0.50 1 d PD . . F18 F 0.0538(5) -0.112(2) 0.3357(5) 0.076(3) Uani 0.50 1 d PD . . F19 F 0.1153(2) 0.024(4) 0.3303(6) 0.087(4) Uani 0.50 1 d PD . . F17A F 0.0960(8) 0.258(4) 0.3056(5) 0.109(4) Uani 0.50 1 d PD . . F18A F 0.0942(11) -0.130(3) 0.3417(5) 0.210(10) Uani 0.50 1 d PD . . F19A F 0.0349(2) 0.113(6) 0.3103(6) 0.142(7) Uani 0.50 1 d PD . . C20 C 0.0786(3) 0.3457(17) 0.5681(3) 0.046(13) Uani 0.50 1 d PG . . C21 C 0.10909(18) 0.2760(15) 0.6293(4) 0.045(3) Uani 0.50 1 d PG . . C22 C 0.0944(3) 0.2627(16) 0.6827(3) 0.059(3) Uani 0.50 1 d PG . . C23 C 0.0492(3) 0.3193(18) 0.6749(3) 0.079(13) Uani 0.50 1 d PG . . C24 C 0.0188(2) 0.3890(16) 0.6137(4) 0.057(3) Uani 0.50 1 d PG . . C25 C 0.0335(2) 0.4023(16) 0.5603(3) 0.052(3) Uani 0.50 1 d PG . . H21A H 0.1401 0.2374 0.6350 0.080 Uiso 0.50 1 d P . . H22A H 0.1151 0.2114 0.7254 0.080 Uiso 0.50 1 d P . . H23A H 0.0386 0.3073 0.7123 0.080 Uiso 0.50 1 d P . . H24A H -0.0129 0.4290 0.6089 0.080 Uiso 0.50 1 d P . . H25A H 0.0121 0.4549 0.5184 0.080 Uiso 0.50 1 d P . . C20X C 0.0795(2) 0.3224(19) 0.5697(3) 0.037(12) Uani 0.50 1 d PG . . C21X C 0.0734(3) 0.0918(14) 0.6007(4) 0.058(3) Uani 0.50 1 d PG . . C22X C 0.0580(3) 0.1060(16) 0.6534(4) 0.074(4) Uani 0.50 1 d PG . . C23X C 0.0486(2) 0.351(2) 0.6751(3) 0.054(10) Uani 0.50 1 d PG . . C24X C 0.0547(3) 0.5811(15) 0.6442(4) 0.061(3) Uani 0.50 1 d PG . . C25X C 0.0702(3) 0.5670(15) 0.5915(4) 0.049(3) Uani 0.50 1 d PG . . H21X H 0.0802 -0.0785 0.5865 0.080 Uiso 0.50 1 d P . . H22X H 0.0540 -0.0533 0.6757 0.080 Uiso 0.50 1 d P . . H23X H 0.0376 0.3616 0.7119 0.080 Uiso 0.50 1 d P . . H24X H 0.0475 0.7513 0.6588 0.080 Uiso 0.50 1 d P . . H25X H 0.0738 0.7260 0.5696 0.080 Uiso 0.50 1 d P . . 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 0.042(2) 0.047(3) 0.033(2) -0.002(2) 0.0094(19) -0.002(2) N2 0.049(3) 0.060(3) 0.033(2) -0.003(2) 0.011(2) -0.001(2) C3 0.042(3) 0.070(4) 0.040(3) -0.007(3) 0.009(3) -0.006(3) C4 0.048(3) 0.080(4) 0.049(3) -0.013(3) 0.013(3) -0.017(3) C5 0.035(3) 0.054(3) 0.041(3) 0.001(3) 0.011(2) 0.000(3) C6 0.038(3) 0.036(3) 0.038(3) 0.001(2) 0.011(2) 0.004(2) N7 0.054(3) 0.088(4) 0.038(3) -0.009(2) 0.018(2) -0.032(3) C8 0.055(3) 0.087(4) 0.035(3) -0.005(3) 0.017(3) -0.018(3) C9 0.040(3) 0.036(3) 0.035(3) 0.000(2) 0.014(2) 0.000(2) C10 0.076(4) 0.056(4) 0.045(3) -0.002(3) 0.029(3) -0.021(3) C11 0.086(4) 0.062(4) 0.034(3) -0.009(3) 0.023(3) -0.021(3) S12 0.0512(8) 0.0410(8) 0.0441(8) -0.0025(6) 0.0157(6) -0.0048(7) O13 0.081(3) 0.063(3) 0.056(2) 0.0051(19) 0.0261(19) -0.027(2) O14 0.080(3) 0.053(2) 0.055(2) -0.0140(19) 0.0298(19) 0.002(2) C15 0.048(3) 0.063(4) 0.071(4) -0.004(3) 0.007(3) -0.002(3) C16 0.051(4) 0.097(6) 0.052(4) -0.012(4) 0.016(3) -0.022(4) F17 0.151(12) 0.093(8) 0.033(4) 0.004(4) -0.026(7) 0.012(8) F18 0.086(6) 0.075(7) 0.071(6) -0.032(5) 0.033(6) -0.025(6) F19 0.061(5) 0.141(13) 0.064(7) -0.040(9) 0.028(4) -0.009(7) F17A 0.129(9) 0.144(12) 0.053(6) -0.023(6) 0.031(7) -0.061(10) F18A 0.42(3) 0.102(14) 0.073(7) -0.015(8) 0.032(18) 0.114(18) F19A 0.064(6) 0.27(2) 0.084(8) -0.079(11) 0.014(6) -0.050(12) C20 0.03(2) 0.05(2) 0.05(2) 0.027(13) -0.003(18) -0.009(13) C21 0.045(6) 0.044(7) 0.049(7) 0.010(5) 0.018(6) -0.002(6) C22 0.065(8) 0.064(8) 0.041(6) 0.004(6) 0.010(6) -0.019(7) C23 0.15(3) 0.057(19) 0.05(2) -0.004(13) 0.05(2) -0.038(17) C24 0.059(7) 0.052(8) 0.073(8) 0.002(6) 0.039(7) 0.001(6) C25 0.037(6) 0.057(7) 0.057(7) 0.005(6) 0.009(5) 0.000(6) C20X 0.04(2) 0.035(19) 0.04(2) -0.024(11) 0.020(19) 0.003(13) C21X 0.072(8) 0.030(7) 0.077(8) 0.002(6) 0.034(7) -0.001(6) C22X 0.106(10) 0.074(10) 0.059(8) 0.003(7) 0.051(7) -0.028(8) C23X 0.036(13) 0.073(19) 0.06(2) -0.023(13) 0.033(14) -0.009(12) C24X 0.060(7) 0.055(9) 0.075(8) -0.016(7) 0.036(6) -0.015(6) C25X 0.048(7) 0.045(8) 0.053(7) -0.001(6) 0.017(6) -0.006(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 N2 1.365(5) . ? N1 C5 1.379(6) . ? N1 C6 1.428(6) . ? N2 C3 1.319(6) . ? C3 C4 1.396(6) . ? C3 C16 1.486(5) . ? C4 C5 1.360(6) . ? C5 C20 1.479(7) . ? C5 C20X 1.490(7) . ? C6 N7 1.303(5) . ? C6 C11 1.370(6) . ? N7 C8 1.336(6) . ? C8 C9 1.367(6) . ? C9 C10 1.368(6) . ? C9 S12 1.763(4) . ? C10 C11 1.376(7) . ? S12 O14 1.428(3) . ? S12 O13 1.433(3) . ? S12 C15 1.749(5) . ? C16 F17 1.286(7) . ? C16 F18A 1.288(8) . ? C16 F19A 1.311(8) . ? C16 F19 1.314(7) . ? C16 F18 1.334(7) . ? C16 F17A 1.339(7) . ? F17 F19A 1.119(12) . ? F17 F17A 1.203(11) . ? F18 F18A 1.22(2) . ? F18 F19A 1.311(18) . ? F19 F18A 1.10(2) . ? F19 F17A 1.350(13) . ? C20 C25X 1.293(11) . ? C20 C21 1.3900 . ? C20 C25 1.3900 . ? C20 C21X 1.501(11) . ? C21 C20X 1.328(11) . ? C21 C22 1.3900 . ? C21 C21X 1.419(11) . ? C21 C25X 1.904(10) . ? C21 C22X 2.032(10) . ? C22 C22X 1.352(11) . ? C22 C23 1.3900 . ? C22 C23X 1.450(12) . ? C22 C21X 1.886(10) . ? C22 C24X 2.027(10) . ? C23 C22X 1.242(12) . ? C23 C24 1.3900 . ? C23 C24X 1.518(12) . ? C24 C23X 1.355(11) . ? C24 C25 1.3900 . ? C24 C24X 1.459(11) . ? C24 C22X 1.887(11) . ? C24 C25X 2.036(10) . ? C25 C25X 1.389(10) . ? C25 C20X 1.438(11) . ? C25 C24X 1.939(10) . ? C25 C21X 2.008(10) . ? C20X C21X 1.3900 . ? C20X C25X 1.3900 . ? C21X C22X 1.3900 . ? C22X C23X 1.3900 . ? C23X C24X 1.3900 . ? C24X C25X 1.3900 . ? 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 N2 N1 C5 111.7(4) . . ? N2 N1 C6 116.7(4) . . ? C5 N1 C6 131.6(4) . . ? C3 N2 N1 104.7(3) . . ? N2 C3 C4 111.5(4) . . ? N2 C3 C16 120.5(4) . . ? C4 C3 C16 128.1(5) . . ? C5 C4 C3 106.7(4) . . ? C4 C5 N1 105.4(4) . . ? C4 C5 C20 127.4(5) . . ? N1 C5 C20 126.9(5) . . ? C4 C5 C20X 125.3(5) . . ? N1 C5 C20X 129.3(5) . . ? C20 C5 C20X 4.8(5) . . ? N7 C6 C11 124.3(4) . . ? N7 C6 N1 116.3(4) . . ? C11 C6 N1 119.5(4) . . ? C6 N7 C8 117.1(4) . . ? N7 C8 C9 123.7(4) . . ? C10 C9 C8 117.7(4) . . ? C10 C9 S12 121.7(4) . . ? C8 C9 S12 120.7(4) . . ? C9 C10 C11 119.7(4) . . ? C6 C11 C10 117.6(4) . . ? O14 S12 O13 118.8(2) . . ? O14 S12 C15 107.4(2) . . ? O13 S12 C15 109.7(2) . . ? O14 S12 C9 109.1(2) . . ? O13 S12 C9 107.2(2) . . ? C15 S12 C9 103.7(2) . . ? F17 C16 F18A 134.3(7) . . ? F17 C16 F19A 51.0(6) . . ? F18A C16 F19A 109.9(8) . . ? F17 C16 F19 110.5(7) . . ? F18A C16 F19 50.2(10) . . ? F19A C16 F19 136.1(7) . . ? F17 C16 F18 107.0(6) . . ? F18A C16 F18 55.6(11) . . ? F19A C16 F18 59.4(8) . . ? F19 C16 F18 103.5(6) . . ? F17 C16 F17A 54.5(6) . . ? F18A C16 F17A 107.6(8) . . ? F19A C16 F17A 103.2(7) . . ? F19 C16 F17A 61.1(6) . . ? F18 C16 F17A 138.4(6) . . ? F17 C16 C3 112.4(5) . . ? F18A C16 C3 113.3(6) . . ? F19A C16 C3 111.4(6) . . ? F19 C16 C3 112.5(5) . . ? F18 C16 C3 110.5(5) . . ? F17A C16 C3 111.0(5) . . ? F19A F17 F17A 126.8(10) . . ? F19A F17 C16 65.6(6) . . ? F17A F17 C16 65.0(5) . . ? F18A F18 F19A 114.0(9) . . ? F18A F18 C16 60.3(7) . . ? F19A F18 C16 59.4(5) . . ? F18A F19 C16 63.7(8) . . ? F18A F19 F17A 119.3(10) . . ? C16 F19 F17A 60.4(5) . . ? F17 F17A C16 60.5(5) . . ? F17 F17A F19 113.4(8) . . ? C16 F17A F19 58.5(5) . . ? F19 F18A F18 126.5(10) . . ? F19 F18A C16 66.1(6) . . ? F18 F18A C16 64.1(7) . . ? F17 F19A C16 63.3(5) . . ? F17 F19A F18 119.9(11) . . ? C16 F19A F18 61.2(7) . . ? C25X C20 C21 90.4(5) . . ? C25X C20 C25 62.3(5) . . ? C21 C20 C25 120.0 . . ? C25X C20 C5 126.1(7) . . ? C21 C20 C5 120.7(6) . . ? C25 C20 C5 118.4(6) . . ? C25X C20 C21X 118.8(6) . . ? C21 C20 C21X 58.7(4) . . ? C25 C20 C21X 87.9(4) . . ? C5 C20 C21X 115.0(7) . . ? C20X C21 C22 120.4(4) . . ? C20X C21 C20 4.5(5) . . ? C22 C21 C20 120.0 . . ? C20X C21 C21X 60.7(4) . . ? C22 C21 C21X 84.3(5) . . ? C20 C21 C21X 64.6(5) . . ? C20X C21 C25X 46.9(3) . . ? C22 C21 C25X 93.0(3) . . ? C20 C21 C25X 42.8(4) . . ? C21X C21 C25X 91.6(4) . . ? C20X C21 C22X 89.0(4) . . ? C22 C21 C22X 41.5(4) . . ? C20 C21 C22X 90.9(3) . . ? C21X C21 C22X 43.1(3) . . ? C25X C21 C22X 89.8(3) . . ? C22X C22 C21 95.6(5) . . ? C22X C22 C23 53.9(5) . . ? C21 C22 C23 120.0 . . ? C22X C22 C23X 59.3(4) . . ? C21 C22 C23X 119.0(4) . . ? C23 C22 C23X 6.0(5) . . ? C22X C22 C21X 47.4(3) . . ? C21 C22 C21X 48.5(4) . . ? C23 C22 C21X 88.3(3) . . ? C23X C22 C21X 91.4(4) . . ? C22X C22 C24X 88.5(5) . . ? C21 C22 C24X 86.9(3) . . ? C23 C22 C24X 48.4(3) . . ? C23X C22 C24X 43.3(3) . . ? C21X C22 C24X 90.5(3) . . ? C22X C23 C24 91.4(5) . . ? C22X C23 C22 61.5(5) . . ? C24 C23 C22 120.0 . . ? C22X C23 C24X 121.1(6) . . ? C24 C23 C24X 60.0(4) . . ? C22 C23 C24X 88.3(4) . . ? C23X C24 C25 121.3(4) . . ? C23X C24 C23 6.5(5) . . ? C25 C24 C23 120.0 . . ? C23X C24 C24X 59.1(4) . . ? C25 C24 C24X 85.7(5) . . ? C23 C24 C24X 64.3(5) . . ? C23X C24 C22X 47.4(3) . . ? C25 C24 C22X 94.0(4) . . ? C23 C24 C22X 41.2(4) . . ? C24X C24 C22X 91.1(4) . . ? C23X C24 C25X 88.1(4) . . ? C25 C24 C25X 42.9(3) . . ? C23 C24 C25X 90.2(3) . . ? C24X C24 C25X 43.1(3) . . ? C22X C24 C25X 90.2(3) . . ? C25X C25 C24 94.2(5) . . ? C25X C25 C20 55.5(5) . . ? C24 C25 C20 120.0 . . ? C25X C25 C20X 58.9(4) . . ? C24 C25 C20X 117.9(4) . . ? C20 C25 C20X 4.6(5) . . ? C25X C25 C24X 45.8(3) . . ? C24 C25 C24X 48.6(4) . . ? C20 C25 C24X 88.7(3) . . ? C20X C25 C24X 89.7(4) . . ? C25X C25 C21X 88.3(4) . . ? C24 C25 C21X 86.0(3) . . ? C20 C25 C21X 48.3(3) . . ? C20X C25 C21X 43.8(3) . . ? C24X C25 C21X 89.5(3) . . ? C21 C20X C21X 62.9(5) . . ? C21 C20X C25X 88.9(5) . . ? C21X C20X C25X 120.0 . . ? C21 C20X C25 121.0(6) . . ? C21X C20X C25 90.5(4) . . ? C25X C20X C25 58.8(4) . . ? C21 C20X C5 124.4(6) . . ? C21X C20X C5 121.4(7) . . ? C25X C20X C5 118.2(7) . . ? C25 C20X C5 114.6(5) . . ? C20X C21X C22X 120.0 . . ? C20X C21X C21 56.4(5) . . ? C22X C21X C21 92.7(5) . . ? C20X C21X C20 2.2(4) . . ? C22X C21X C20 118.0(4) . . ? C21 C21X C20 56.8(4) . . ? C20X C21X C22 90.8(3) . . ? C22X C21X C22 45.7(4) . . ? C21 C21X C22 47.2(3) . . ? C20 C21X C22 89.9(4) . . ? C20X C21X C25 45.7(3) . . ? C22X C21X C25 88.9(3) . . ? C21 C21X C25 87.5(4) . . ? C20 C21X C25 43.8(3) . . ? C22 C21X C25 91.0(3) . . ? C23 C22X C22 64.6(5) . . ? C23 C22X C23X 2.7(4) . . ? C22 C22X C23X 63.9(5) . . ? C23 C22X C21X 122.6(4) . . ? C22 C22X C21X 86.9(5) . . ? C23X C22X C21X 120.0 . . ? C23 C22X C24 47.4(4) . . ? C22 C22X C24 94.6(5) . . ? C23X C22X C24 45.8(4) . . ? C21X C22X C24 90.9(3) . . ? C23 C22X C21 91.4(5) . . ? C22 C22X C21 42.9(3) . . ? C23X C22X C21 89.3(3) . . ? C21X C22X C21 44.2(3) . . ? C24 C22X C21 90.3(3) . . ? C24 C23X C22X 86.8(5) . . ? C24 C23X C24X 64.2(5) . . ? C22X C23X C24X 120.0 . . ? C24 C23X C22 118.2(6) . . ? C22X C23X C22 56.8(5) . . ? C24X C23X C22 91.1(4) . . ? C23X C24X C25X 120.0 . . ? C23X C24X C24 56.7(5) . . ? C25X C24X C24 91.2(4) . . ? C23X C24X C23 3.8(4) . . ? C25X C24X C23 116.2(4) . . ? C24 C24X C23 55.6(4) . . ? C23X C24X C25 90.4(3) . . ? C25X C24X C25 45.8(4) . . ? C24 C24X C25 45.6(3) . . ? C23 C24X C25 87.4(4) . . ? C23X C24X C22 45.7(3) . . ? C25X C24X C22 87.9(3) . . ? C24 C24X C22 85.7(4) . . ? C23 C24X C22 43.3(3) . . ? C25 C24X C22 89.0(3) . . ? C20 C25X C25 62.3(5) . . ? C20 C25X C24X 123.1(4) . . ? C25 C25X C24X 88.5(5) . . ? C20 C25X C20X 3.3(4) . . ? C25 C25X C20X 62.3(5) . . ? C24X C25X C20X 120.0 . . ? C20 C25X C21 46.9(3) . . ? C25 C25X C21 92.6(5) . . ? C24X C25X C21 92.0(4) . . ? C20X C25X C21 44.2(4) . . ? C20 C25X C24 89.8(4) . . ? C25 C25X C24 42.9(3) . . ? C24X C25X C24 45.8(3) . . ? C20X C25X C24 87.9(3) . . ? C21 C25X C24 89.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 49.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.176 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.044 data_f579 _database_code_depnum_ccdc_archive 'CCDC 263087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 F2 N3 O2 S' _chemical_formula_weight 349.35 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 P2(1)/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 10.614(2) _cell_length_b 7.4840(10) _cell_length_c 20.523(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.250(10) _cell_angle_gamma 90.00 _cell_volume 1620.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.108 _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 293(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 'CCD area detector' _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 1790 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 49.98 _reflns_number_total 1674 _reflns_number_gt 1271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0640P)^2^+0.4721P] 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 SHELXL _refine_ls_extinction_coef 0.0027(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1674 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 S1X S 0.53678(10) 0.07320(14) 0.13470(5) 0.0474(4) Uani 1 1 d . . . C1 C 0.6923(4) -0.4103(5) 0.17403(18) 0.0395(10) Uani 1 1 d . . . H1B H 0.6923 -0.5017 0.2047 0.080 Uiso 1 1 calc R . . C2 C 0.6245(4) -0.2552(5) 0.18015(19) 0.0425(11) Uani 1 1 d . . . H2B H 0.5787 -0.2379 0.2158 0.080 Uiso 1 1 calc R . . C3 C 0.6259(3) -0.1257(5) 0.13194(18) 0.0341(10) Uani 1 1 d . . . C4 C 0.6990(4) -0.1522(5) 0.08154(18) 0.0421(11) Uani 1 1 d . . . H4B H 0.7006 -0.0631 0.0500 0.080 Uiso 1 1 calc R . . N5 N 0.7679(3) -0.2999(4) 0.07550(15) 0.0409(9) Uani 1 1 d . . . C6 C 0.7603(3) -0.4249(5) 0.12067(17) 0.0320(9) Uani 1 1 d . . . N7 N 0.8295(3) -0.5840(4) 0.11201(14) 0.0356(8) Uani 1 1 d . . . N8 N 0.8810(3) -0.6684(4) 0.16759(15) 0.0419(9) Uani 1 1 d . . . C9 C 0.9420(4) -0.8066(5) 0.14508(19) 0.0418(10) Uani 1 1 d . . . C10 C 0.9306(4) -0.8132(5) 0.07702(19) 0.0428(11) Uani 1 1 d . . . H10B H 0.9655 -0.8980 0.0512 0.080 Uiso 1 1 calc R . . C11 C 0.8573(3) -0.6688(5) 0.05564(18) 0.0349(10) Uani 1 1 d . . . C12 C 0.8096(3) -0.6191(5) -0.01192(17) 0.0342(10) Uani 1 1 d . . . C13 C 0.6855(4) -0.5654(5) -0.0298(2) 0.0461(11) Uani 1 1 d . . . H13B H 0.6295 -0.5575 0.0019 0.080 Uiso 1 1 calc R . . C14 C 0.6446(5) -0.5239(6) -0.0938(2) 0.0576(13) Uani 1 1 d . . . H14B H 0.5614 -0.4876 -0.1052 0.080 Uiso 1 1 calc R . . C15 C 0.7266(6) -0.5360(6) -0.1409(2) 0.0687(15) Uani 1 1 d . . . H15B H 0.6991 -0.5063 -0.1841 0.080 Uiso 1 1 calc R . . C16 C 0.8497(5) -0.5922(6) -0.1244(2) 0.0650(14) Uani 1 1 d . . . H16B H 0.9044 -0.6036 -0.1566 0.080 Uiso 1 1 calc R . . C17 C 0.8914(4) -0.6313(5) -0.0603(2) 0.0486(11) Uani 1 1 d . . . H17B H 0.9750 -0.6663 -0.0491 0.080 Uiso 1 1 calc R . . C18 C 1.0086(4) -0.9308(6) 0.1940(2) 0.0521(12) Uani 1 1 d . . . H18B H 1.0149 -0.8788 0.2380 0.080 Uiso 1 1 calc R . . F19 F 0.9482(3) -1.0893(4) 0.19267(17) 0.1126(13) Uani 1 1 d . . . F20 F 1.1234(3) -0.9713(5) 0.17728(15) 0.1089(13) Uani 1 1 d . . . O21 O 0.5449(4) 0.1342(5) 0.20054(16) 0.0854(11) Uani 1 1 d . . . O22 O 0.5756(3) 0.1905(4) 0.08583(17) 0.0782(11) Uani 1 1 d . . . C23 C 0.3814(4) 0.0083(7) 0.1108(3) 0.0802(17) Uani 1 1 d . . . H23A H 0.3266 0.1102 0.1112 0.080 Uiso 1 1 calc R . . H23B H 0.3564 -0.0803 0.1407 0.080 Uiso 1 1 calc R . . H23C H 0.3755 -0.0410 0.0674 0.080 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 S1X 0.0469(7) 0.0366(7) 0.0607(8) -0.0051(6) 0.0152(5) 0.0063(5) C1 0.040(2) 0.042(3) 0.036(2) 0.000(2) 0.0043(19) 0.001(2) C2 0.041(3) 0.049(3) 0.040(3) -0.003(2) 0.013(2) 0.002(2) C3 0.035(2) 0.031(2) 0.038(2) -0.005(2) 0.0074(19) 0.0012(18) C4 0.052(3) 0.035(3) 0.040(3) 0.000(2) 0.012(2) 0.002(2) N5 0.046(2) 0.038(2) 0.040(2) -0.0021(18) 0.0120(16) 0.0025(18) C6 0.030(2) 0.033(2) 0.033(2) -0.004(2) 0.0019(18) 0.002(2) N7 0.0368(18) 0.037(2) 0.0321(19) -0.0001(17) 0.0018(15) 0.0073(17) N8 0.043(2) 0.042(2) 0.040(2) 0.0038(18) -0.0012(16) 0.0088(19) C9 0.040(2) 0.043(3) 0.041(3) -0.001(2) 0.002(2) 0.009(2) C10 0.046(2) 0.039(3) 0.043(3) -0.003(2) 0.003(2) 0.010(2) C11 0.034(2) 0.037(2) 0.034(2) -0.002(2) 0.0062(18) 0.003(2) C12 0.035(2) 0.032(2) 0.035(2) -0.0047(19) 0.0011(19) -0.0006(19) C13 0.047(3) 0.044(3) 0.044(3) -0.010(2) -0.006(2) 0.002(2) C14 0.063(3) 0.045(3) 0.059(3) -0.011(2) -0.019(3) 0.008(2) C15 0.107(5) 0.053(3) 0.042(3) 0.003(2) -0.012(3) -0.001(3) C16 0.092(4) 0.062(3) 0.044(3) 0.001(3) 0.022(3) -0.001(3) C17 0.051(3) 0.053(3) 0.043(3) -0.005(2) 0.010(2) -0.003(2) C18 0.049(3) 0.045(3) 0.060(3) -0.001(2) -0.004(2) 0.008(3) F19 0.122(3) 0.067(2) 0.133(3) 0.037(2) -0.060(2) -0.012(2) F20 0.077(2) 0.154(3) 0.098(2) 0.042(2) 0.0150(17) 0.067(2) O21 0.107(3) 0.082(3) 0.067(2) -0.033(2) 0.0107(19) 0.036(2) O22 0.083(2) 0.0459(19) 0.114(3) 0.0266(19) 0.047(2) 0.0139(18) C23 0.044(3) 0.055(3) 0.141(5) 0.002(3) 0.007(3) 0.012(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 S1X O21 1.420(3) . ? S1X O22 1.427(3) . ? S1X C23 1.737(5) . ? S1X C3 1.768(4) . ? C1 C2 1.379(5) . ? C1 C6 1.380(5) . ? C2 C3 1.386(5) . ? C3 C4 1.373(5) . ? C4 N5 1.339(5) . ? N5 C6 1.326(5) . ? C6 N7 1.420(5) . ? N7 N8 1.365(4) . ? N7 C11 1.379(4) . ? N8 C9 1.329(5) . ? C9 C10 1.390(5) . ? C9 C18 1.489(6) . ? C10 C11 1.375(5) . ? C11 C12 1.471(5) . ? C12 C13 1.387(5) . ? C12 C17 1.391(5) . ? C13 C14 1.374(6) . ? C14 C15 1.372(6) . ? C15 C16 1.379(7) . ? C16 C17 1.372(6) . ? C18 F20 1.337(5) . ? C18 F19 1.347(5) . ? 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 O21 S1X O22 118.6(2) . . ? O21 S1X C23 108.4(3) . . ? O22 S1X C23 108.2(2) . . ? O21 S1X C3 108.90(19) . . ? O22 S1X C3 107.39(18) . . ? C23 S1X C3 104.5(2) . . ? C2 C1 C6 117.5(4) . . ? C1 C2 C3 118.5(3) . . ? C4 C3 C2 119.2(4) . . ? C4 C3 S1X 119.6(3) . . ? C2 C3 S1X 121.2(3) . . ? N5 C4 C3 123.2(4) . . ? C6 N5 C4 116.2(3) . . ? N5 C6 C1 125.2(4) . . ? N5 C6 N7 115.6(3) . . ? C1 C6 N7 119.2(3) . . ? N8 N7 C11 112.7(3) . . ? N8 N7 C6 116.7(3) . . ? C11 N7 C6 130.6(3) . . ? C9 N8 N7 103.6(3) . . ? N8 C9 C10 112.6(3) . . ? N8 C9 C18 117.7(4) . . ? C10 C9 C18 129.7(4) . . ? C11 C10 C9 106.1(3) . . ? C10 C11 N7 105.0(3) . . ? C10 C11 C12 128.6(3) . . ? N7 C11 C12 126.2(3) . . ? C13 C12 C17 118.6(4) . . ? C13 C12 C11 122.8(3) . . ? C17 C12 C11 118.6(3) . . ? C14 C13 C12 120.7(4) . . ? C15 C14 C13 120.0(4) . . ? C14 C15 C16 120.2(4) . . ? C17 C16 C15 119.9(4) . . ? C16 C17 C12 120.6(4) . . ? F20 C18 F19 103.9(4) . . ? F20 C18 C9 110.4(4) . . ? F19 C18 C9 110.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 49.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.042 data_f874 _database_code_depnum_ccdc_archive 'CCDC 263088' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N3 O3 S' _chemical_formula_weight 331.39 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 15.9809(10) _cell_length_b 9.4557(6) _cell_length_c 10.5313(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.4710(10) _cell_angle_gamma 90.00 _cell_volume 1591.34(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.222 _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 298(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 'CCD area detector' _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 8021 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 20.82 _reflns_number_total 1663 _reflns_number_gt 1342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0635P)^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 SHELXL _refine_ls_extinction_coef 0.0120(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1663 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 -0.20483(13) 0.3613(2) 0.5908(2) 0.0472(6) Uani 1 1 d . . . C2 C -0.12782(17) 0.3570(3) 0.6410(3) 0.0470(8) Uani 1 1 d . . . H2 H -0.1105 0.4326 0.6962 0.080 Uiso 1 1 calc R . . C3 C -0.07207(16) 0.2491(3) 0.6173(2) 0.0423(7) Uani 1 1 d . . . C4 C -0.09800(18) 0.1390(3) 0.5396(3) 0.0506(8) Uani 1 1 d . . . H4 H -0.0608 0.0617 0.5223 0.080 Uiso 1 1 calc R . . C5 C -0.17646(17) 0.1406(3) 0.4880(3) 0.0465(8) Uani 1 1 d . . . H5 H -0.1955 0.0650 0.4343 0.080 Uiso 1 1 calc R . . C6 C -0.22790(16) 0.2543(3) 0.5149(2) 0.0408(7) Uani 1 1 d . . . N7 N -0.30600(14) 0.2660(2) 0.4624(2) 0.0548(7) Uani 1 1 d . . . N8 N -0.34863(15) 0.1462(2) 0.4208(2) 0.0510(7) Uani 1 1 d . . . C9 C -0.42423(18) 0.1821(3) 0.3968(3) 0.0509(8) Uani 1 1 d . . . C10 C -0.44227(19) 0.3331(3) 0.4203(3) 0.0776(11) Uani 1 1 d . . . H10A H -0.4875 0.3436 0.4789 0.080 Uiso 1 1 calc R . . H10B H -0.4566 0.3808 0.3426 0.080 Uiso 1 1 calc R . . C11 C -0.36083(17) 0.3913(3) 0.4765(3) 0.0568(8) Uani 1 1 d . . . C12 C -0.32691(16) 0.5155(3) 0.4026(3) 0.0490(8) Uani 1 1 d . . . C13 C -0.33594(17) 0.6518(3) 0.4475(3) 0.0550(8) Uani 1 1 d . . . H13 H -0.3612 0.6678 0.5287 0.080 Uiso 1 1 calc R . . C14 C -0.3087(2) 0.7658(3) 0.3758(4) 0.0704(10) Uani 1 1 d . . . H14 H -0.3152 0.8601 0.4078 0.080 Uiso 1 1 calc R . . C15 C -0.2729(2) 0.7451(4) 0.2606(4) 0.0742(10) Uani 1 1 d . . . H15 H -0.2534 0.8242 0.2120 0.080 Uiso 1 1 calc R . . C16 C -0.2649(2) 0.6116(5) 0.2152(3) 0.0764(11) Uani 1 1 d . . . H16 H -0.2404 0.5968 0.1333 0.080 Uiso 1 1 calc R . . C17 C -0.29144(19) 0.4973(3) 0.2846(3) 0.0640(9) Uani 1 1 d . . . H17 H -0.2853 0.4037 0.2507 0.080 Uiso 1 1 calc R . . O18 O -0.37516(13) 0.4218(3) 0.6049(2) 0.0715(8) Uani 1 1 d . . . H18X H -0.331(2) 0.436(4) 0.634(3) 0.080 Uiso 1 1 d . . . C19 C -0.48843(19) 0.0832(3) 0.3479(3) 0.0732(10) Uani 1 1 d . . . H19A H -0.4637 -0.0082 0.3351 0.080 Uiso 1 1 calc R . . H19B H -0.5103 0.1179 0.2688 0.080 Uiso 1 1 calc R . . H19C H -0.5329 0.0756 0.4082 0.080 Uiso 1 1 calc R . . S20 S 0.03011(4) 0.25518(8) 0.67961(7) 0.0512(3) Uani 1 1 d . . . O21 O 0.06891(13) 0.1219(2) 0.6575(2) 0.0780(7) Uani 1 1 d . . . O22 O 0.02806(13) 0.3069(3) 0.8059(2) 0.0930(8) Uani 1 1 d . . . C23 C 0.07959(19) 0.3794(4) 0.5852(3) 0.0800(11) Uani 1 1 d . . . H23A H 0.1381 0.3822 0.6064 0.080 Uiso 1 1 calc R . . H23B H 0.0553 0.4708 0.5994 0.080 Uiso 1 1 calc R . . H23C H 0.0728 0.3539 0.4975 0.080 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 0.0371(16) 0.0451(15) 0.0593(16) -0.0052(13) -0.0107(12) 0.0034(12) C2 0.0425(19) 0.0481(19) 0.0502(18) -0.0014(14) -0.0076(15) -0.0008(16) C3 0.0369(17) 0.0448(18) 0.0451(18) 0.0035(14) -0.0048(14) 0.0012(15) C4 0.041(2) 0.0458(19) 0.065(2) -0.0016(16) -0.0044(15) 0.0056(15) C5 0.0400(19) 0.0446(19) 0.0548(19) -0.0052(14) -0.0066(15) 0.0020(16) C6 0.0328(18) 0.0427(19) 0.0468(18) 0.0038(15) -0.0057(14) -0.0002(15) N7 0.0378(17) 0.0387(15) 0.088(2) -0.0048(13) -0.0207(14) 0.0005(12) N8 0.0422(17) 0.0530(17) 0.0575(16) -0.0013(12) -0.0099(12) -0.0055(13) C9 0.039(2) 0.061(2) 0.0526(19) 0.0001(15) -0.0077(15) -0.0071(17) C10 0.046(2) 0.067(2) 0.119(3) 0.003(2) -0.024(2) -0.0027(18) C11 0.0364(19) 0.054(2) 0.079(3) -0.0057(19) -0.0124(16) 0.0074(16) C12 0.0395(18) 0.045(2) 0.062(2) -0.0063(17) -0.0192(15) 0.0076(15) C13 0.0415(19) 0.054(2) 0.069(2) -0.0109(19) -0.0143(15) 0.0058(16) C14 0.064(2) 0.050(2) 0.097(3) -0.008(2) -0.029(2) 0.0069(19) C15 0.076(3) 0.068(3) 0.078(3) 0.015(2) -0.026(2) 0.001(2) C16 0.091(3) 0.082(3) 0.056(2) 0.005(2) -0.0135(19) 0.012(2) C17 0.073(2) 0.053(2) 0.066(2) -0.0106(19) -0.0161(19) 0.0132(18) O18 0.0515(15) 0.0846(17) 0.0784(18) 0.0008(13) 0.0048(13) 0.0068(13) C19 0.053(2) 0.085(3) 0.081(2) -0.0096(19) -0.0130(18) -0.0123(18) S20 0.0413(5) 0.0567(6) 0.0553(6) 0.0056(4) -0.0139(4) 0.0052(4) O21 0.0546(14) 0.0509(13) 0.128(2) 0.0018(13) -0.0324(13) 0.0154(11) O22 0.0641(16) 0.159(2) 0.0556(15) -0.0256(15) -0.0194(11) 0.0161(15) C23 0.050(2) 0.086(2) 0.104(3) 0.031(2) -0.0244(19) -0.0157(19) _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 1.336(3) . ? N1 C6 1.340(3) . ? C2 C3 1.379(3) . ? C3 C4 1.385(4) . ? C3 S20 1.756(3) . ? C4 C5 1.363(4) . ? C5 C6 1.384(3) . ? C6 N7 1.366(3) . ? N7 N8 1.391(3) . ? N7 C11 1.482(3) . ? N8 C9 1.278(3) . ? C9 C19 1.478(4) . ? C9 C10 1.478(4) . ? C10 C11 1.528(4) . ? C11 O18 1.404(4) . ? C11 C12 1.512(4) . ? C12 C13 1.381(4) . ? C12 C17 1.381(4) . ? C13 C14 1.388(4) . ? C14 C15 1.359(4) . ? C15 C16 1.357(5) . ? C16 C17 1.374(4) . ? S20 O22 1.417(2) . ? S20 O21 1.424(2) . ? S20 C23 1.734(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 C6 117.5(2) . . ? N1 C2 C3 123.0(3) . . ? C2 C3 C4 118.2(3) . . ? C2 C3 S20 120.5(2) . . ? C4 C3 S20 121.2(2) . . ? C5 C4 C3 119.8(3) . . ? C4 C5 C6 118.2(3) . . ? N1 C6 N7 115.2(2) . . ? N1 C6 C5 123.2(2) . . ? N7 C6 C5 121.5(2) . . ? C6 N7 N8 120.3(2) . . ? C6 N7 C11 124.3(2) . . ? N8 N7 C11 113.2(2) . . ? C9 N8 N7 107.8(2) . . ? N8 C9 C19 123.6(3) . . ? N8 C9 C10 114.1(2) . . ? C19 C9 C10 122.3(3) . . ? C9 C10 C11 104.3(2) . . ? O18 C11 N7 111.2(2) . . ? O18 C11 C12 113.5(2) . . ? N7 C11 C12 110.8(2) . . ? O18 C11 C10 107.6(3) . . ? N7 C11 C10 100.1(2) . . ? C12 C11 C10 112.8(3) . . ? C13 C12 C17 118.0(3) . . ? C13 C12 C11 120.6(3) . . ? C17 C12 C11 121.2(3) . . ? C12 C13 C14 120.3(3) . . ? C15 C14 C13 120.7(3) . . ? C16 C15 C14 119.3(3) . . ? C15 C16 C17 120.9(3) . . ? C16 C17 C12 120.8(3) . . ? O22 S20 O21 118.18(15) . . ? O22 S20 C23 108.56(18) . . ? O21 S20 C23 107.71(16) . . ? O22 S20 C3 109.49(13) . . ? O21 S20 C3 108.33(13) . . ? C23 S20 C3 103.59(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 20.82 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.038 data_f876 _database_code_depnum_ccdc_archive 'CCDC 263089' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 F3 N3 O3 S' _chemical_formula_weight 385.36 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' 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 8.3741(5) _cell_length_b 19.8459(13) _cell_length_c 10.4665(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.8450(10) _cell_angle_gamma 90.00 _cell_volume 1646.20(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.252 _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 298(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 'CCD area detector' _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 8453 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 20.81 _reflns_number_total 1721 _reflns_number_gt 1463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0471P)^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 1721 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.003 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 0.0423(2) 0.04611(9) 0.26259(19) 0.0445(5) Uani 1 1 d . . . C2 C 0.1007(3) 0.10379(12) 0.3271(2) 0.0443(7) Uani 1 1 d . . . H2 H 0.2100 0.1037 0.3949 0.080 Uiso 1 1 calc R . . C3 C 0.0117(3) 0.16322(11) 0.3010(2) 0.0397(6) Uani 1 1 d . . . C4 C -0.1463(3) 0.16385(12) 0.2014(2) 0.0444(7) Uani 1 1 d . . . H4 H -0.2114 0.2046 0.1817 0.080 Uiso 1 1 calc R . . C5 C -0.2075(3) 0.10610(12) 0.1322(2) 0.0432(6) Uani 1 1 d . . . H5 H -0.3142 0.1055 0.0612 0.080 Uiso 1 1 calc R . . C6 C -0.1099(3) 0.04791(12) 0.1682(2) 0.0388(6) Uani 1 1 d . . . N7 N -0.1691(2) -0.01294(9) 0.10776(19) 0.0443(5) Uani 1 1 d . . . C8 C -0.0885(3) -0.07886(11) 0.1440(2) 0.0429(6) Uani 1 1 d . . . C9 C -0.1806(3) -0.12096(12) 0.0206(2) 0.0505(7) Uani 1 1 d . . . H9A H -0.1042 -0.1370 -0.0240 0.080 Uiso 1 1 calc R . . H9B H -0.2364 -0.1587 0.0448 0.080 Uiso 1 1 calc R . . C10 C -0.3056(3) -0.07232(13) -0.0669(2) 0.0423(7) Uani 1 1 d . . . N11 N -0.2959(2) -0.01295(10) -0.0163(2) 0.0444(5) Uani 1 1 d . . . C12 C -0.4251(3) -0.08857(13) -0.1999(2) 0.0454(7) Uani 1 1 d . . . C13 C -0.5106(3) -0.03803(14) -0.2866(3) 0.0600(8) Uani 1 1 d . . . H13 H -0.4913 0.0083 -0.2597 0.080 Uiso 1 1 calc R . . C14 C -0.6233(4) -0.05428(18) -0.4113(3) 0.0772(9) Uani 1 1 d . . . H14 H -0.6839 -0.0191 -0.4701 0.080 Uiso 1 1 calc R . . C15 C -0.6493(4) -0.11989(19) -0.4519(3) 0.0753(9) Uani 1 1 d . . . H15 H -0.7259 -0.1307 -0.5398 0.080 Uiso 1 1 calc R . . C16 C -0.5667(4) -0.17001(16) -0.3676(3) 0.0680(8) Uani 1 1 d . . . H16 H -0.5859 -0.2161 -0.3960 0.080 Uiso 1 1 calc R . . C17 C -0.4554(3) -0.15491(13) -0.2417(3) 0.0542(7) Uani 1 1 d . . . H17 H -0.3985 -0.1906 -0.1827 0.080 Uiso 1 1 calc R . . C18 C -0.1235(4) -0.10612(14) 0.2676(3) 0.0572(8) Uani 1 1 d . . . F19 F -0.0528(2) -0.07027(8) 0.37946(16) 0.0800(5) Uani 1 1 d . . . F20 F -0.0652(2) -0.16897(8) 0.29402(16) 0.0831(5) Uani 1 1 d . . . F21 F -0.2879(2) -0.10806(8) 0.24977(16) 0.0785(5) Uani 1 1 d . . . O22 O 0.0848(2) -0.07830(9) 0.16710(19) 0.0577(5) Uani 1 1 d . . . H22X H 0.120(4) -0.0455(14) 0.216(3) 0.080 Uiso 1 1 d . . . S23 S 0.09494(9) 0.23627(3) 0.39127(6) 0.0508(3) Uani 1 1 d . . . O24 O 0.2553(2) 0.21935(9) 0.48684(17) 0.0666(6) Uani 1 1 d . . . O25 O -0.0296(2) 0.26619(8) 0.43990(17) 0.0654(5) Uani 1 1 d . . . C26 C 0.1274(4) 0.29077(13) 0.2713(3) 0.0663(8) Uani 1 1 d . . . H26A H 0.0221 0.2988 0.2014 0.080 Uiso 1 1 calc R . . H26B H 0.2059 0.2708 0.2328 0.080 Uiso 1 1 calc R . . H26C H 0.1720 0.3327 0.3136 0.080 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 0.0436(13) 0.0367(13) 0.0498(13) -0.0004(11) 0.0104(11) 0.0026(11) C2 0.0453(16) 0.0434(17) 0.0425(15) 0.0001(13) 0.0119(12) 0.0004(14) C3 0.0488(16) 0.0344(15) 0.0383(15) 0.0011(12) 0.0172(13) 0.0020(13) C4 0.0533(18) 0.0380(16) 0.0432(15) 0.0052(13) 0.0176(14) 0.0068(13) C5 0.0483(16) 0.0352(16) 0.0462(15) 0.0039(13) 0.0154(13) 0.0049(13) C6 0.0427(16) 0.0352(16) 0.0406(15) 0.0020(13) 0.0165(13) -0.0023(14) N7 0.0475(13) 0.0314(13) 0.0484(14) 0.0035(10) 0.0077(11) 0.0037(11) C8 0.0450(17) 0.0328(15) 0.0510(17) 0.0043(12) 0.0155(13) -0.0008(13) C9 0.0574(17) 0.0391(15) 0.0550(17) -0.0009(14) 0.0182(14) 0.0004(14) C10 0.0416(16) 0.0391(17) 0.0502(17) 0.0014(13) 0.0205(14) -0.0021(13) N11 0.0423(13) 0.0411(14) 0.0479(13) 0.0004(11) 0.0119(11) -0.0013(11) C12 0.0418(16) 0.0483(17) 0.0487(17) -0.0006(15) 0.0183(14) 0.0012(14) C13 0.0651(19) 0.0549(18) 0.0563(19) -0.0015(16) 0.0143(16) -0.0005(16) C14 0.081(2) 0.081(3) 0.057(2) 0.0069(18) 0.0050(18) 0.0149(19) C15 0.073(2) 0.086(3) 0.057(2) -0.016(2) 0.0076(17) 0.002(2) C16 0.064(2) 0.066(2) 0.072(2) -0.0224(19) 0.0191(18) -0.0012(18) C17 0.0530(17) 0.0496(19) 0.060(2) -0.0085(14) 0.0185(16) -0.0020(14) C18 0.066(2) 0.0463(19) 0.058(2) 0.0019(16) 0.0186(16) -0.0033(16) F19 0.1143(14) 0.0720(11) 0.0523(10) -0.0002(9) 0.0251(10) -0.0166(10) F20 0.1161(14) 0.0474(10) 0.0808(12) 0.0228(9) 0.0250(10) 0.0086(10) F21 0.0782(13) 0.0791(12) 0.0917(13) 0.0051(9) 0.0461(10) -0.0105(10) O22 0.0448(12) 0.0481(12) 0.0791(14) -0.0062(9) 0.0186(10) 0.0040(10) S23 0.0620(5) 0.0404(4) 0.0470(4) -0.0061(3) 0.0137(4) 0.0022(4) O24 0.0665(13) 0.0582(12) 0.0560(11) -0.0126(9) -0.0067(10) 0.0071(10) O25 0.0809(13) 0.0561(12) 0.0660(13) -0.0106(9) 0.0333(11) 0.0149(10) C26 0.078(2) 0.0452(17) 0.076(2) -0.0024(15) 0.0255(17) -0.0112(15) _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 C6 1.338(3) . ? N1 C2 1.339(3) . ? C2 C3 1.375(3) . ? C3 C4 1.395(3) . ? C3 S23 1.748(2) . ? C4 C5 1.364(3) . ? C5 C6 1.394(3) . ? C6 N7 1.379(3) . ? N7 N11 1.387(2) . ? N7 C8 1.465(3) . ? C8 O22 1.392(3) . ? C8 C18 1.515(3) . ? C8 C9 1.522(3) . ? C9 C10 1.499(3) . ? C10 N11 1.284(3) . ? C10 C12 1.464(3) . ? C12 C17 1.385(3) . ? C12 C13 1.386(3) . ? C13 C14 1.380(4) . ? C14 C15 1.365(4) . ? C15 C16 1.361(4) . ? C16 C17 1.379(3) . ? C18 F21 1.329(3) . ? C18 F19 1.334(3) . ? C18 F20 1.335(3) . ? S23 O25 1.4289(17) . ? S23 O24 1.4314(17) . ? S23 C26 1.744(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 C6 N1 C2 117.1(2) . . ? N1 C2 C3 123.2(2) . . ? C2 C3 C4 118.6(2) . . ? C2 C3 S23 120.53(19) . . ? C4 C3 S23 120.86(19) . . ? C5 C4 C3 119.5(2) . . ? C4 C5 C6 117.7(2) . . ? N1 C6 N7 115.5(2) . . ? N1 C6 C5 123.9(2) . . ? N7 C6 C5 120.6(2) . . ? C6 N7 N11 118.84(19) . . ? C6 N7 C8 126.62(19) . . ? N11 N7 C8 113.07(18) . . ? O22 C8 N7 113.88(18) . . ? O22 C8 C18 109.4(2) . . ? N7 C8 C18 109.9(2) . . ? O22 C8 C9 111.44(19) . . ? N7 C8 C9 101.88(18) . . ? C18 C8 C9 110.1(2) . . ? C10 C9 C8 103.13(19) . . ? N11 C10 C12 121.8(2) . . ? N11 C10 C9 113.6(2) . . ? C12 C10 C9 124.5(2) . . ? C10 N11 N7 108.27(19) . . ? C17 C12 C13 118.6(2) . . ? C17 C12 C10 120.6(2) . . ? C13 C12 C10 120.8(2) . . ? C14 C13 C12 120.1(3) . . ? C15 C14 C13 120.6(3) . . ? C16 C15 C14 119.9(3) . . ? C15 C16 C17 120.4(3) . . ? C16 C17 C12 120.5(3) . . ? F21 C18 F19 106.5(2) . . ? F21 C18 F20 107.1(2) . . ? F19 C18 F20 106.7(2) . . ? F21 C18 C8 111.6(2) . . ? F19 C18 C8 113.9(2) . . ? F20 C18 C8 110.6(2) . . ? O25 S23 O24 118.45(11) . . ? O25 S23 C26 107.46(13) . . ? O24 S23 C26 108.64(13) . . ? O25 S23 C3 109.12(11) . . ? O24 S23 C3 107.67(11) . . ? C26 S23 C3 104.65(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.154 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.030 data_f888 _database_code_depnum_ccdc_archive 'CCDC 263090' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 F3 N2' _chemical_formula_weight 288.27 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' F F 0.0727 0.0534 '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 8.4600(10) _cell_length_b 16.282(2) _cell_length_c 10.7060(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.520(10) _cell_angle_gamma 90.00 _cell_volume 1406.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 31 _cell_measurement_theta_min 11.783 _cell_measurement_theta_max 49.795 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.935 _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 298(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 'Bruker P4' _diffrn_measurement_method 'theta and 2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1570 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 50.00 _reflns_number_total 1449 _reflns_number_gt 978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0771P)^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 SHELXL _refine_ls_extinction_coef 0.0041(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1449 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.002 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 0.0597(4) 0.88616(18) 0.4291(3) 0.0505(8) Uani 1 1 d . . . N2 N 0.0349(4) 0.92848(18) 0.3150(3) 0.0556(9) Uani 1 1 d . . . C3 C -0.1159(5) 0.9062(2) 0.2446(3) 0.0557(10) Uani 1 1 d . . . C4 C -0.1880(5) 0.8512(2) 0.3092(3) 0.0554(11) Uani 1 1 d . . . H4A H -0.2927 0.8276 0.2781 0.080 Uiso 1 1 calc R . . C5 C -0.0728(5) 0.8386(2) 0.4292(3) 0.0489(10) Uani 1 1 d . . . C6 C -0.0902(4) 0.7918(2) 0.5411(3) 0.0485(10) Uani 1 1 d . . . C7 C -0.1554(5) 0.7136(2) 0.5227(4) 0.0626(11) Uani 1 1 d . . . H7A H -0.1827 0.6899 0.4399 0.080 Uiso 1 1 calc R . . C8 C -0.1807(5) 0.6700(3) 0.6251(5) 0.0745(13) Uani 1 1 d . . . H8A H -0.2253 0.6173 0.6112 0.080 Uiso 1 1 calc R . . C9 C -0.1404(5) 0.7038(3) 0.7468(4) 0.0736(13) Uani 1 1 d . . . H9A H -0.1564 0.6742 0.8162 0.080 Uiso 1 1 calc R . . C10 C -0.0758(5) 0.7822(3) 0.7672(4) 0.0679(12) Uani 1 1 d . . . H10A H -0.0489 0.8053 0.8503 0.080 Uiso 1 1 calc R . . C11 C -0.0511(5) 0.8261(2) 0.6652(4) 0.0580(11) Uani 1 1 d . . . H11A H -0.0080 0.8790 0.6795 0.080 Uiso 1 1 calc R . . C12 C -0.1874(8) 0.9416(4) 0.1117(5) 0.0784(14) Uani 1 1 d . . . F13 F -0.3471(11) 0.9336(13) 0.0693(12) 0.138(8) Uani 0.66(3) 1 d P . . F14 F -0.158(2) 1.0199(5) 0.1059(8) 0.117(5) Uani 0.66(3) 1 d P . . F15 F -0.1248(18) 0.9064(9) 0.0274(7) 0.122(6) Uani 0.66(3) 1 d P . . F13A F -0.287(8) 0.893(2) 0.037(3) 0.24(2) Uani 0.34(3) 1 d P . . F14A F -0.276(7) 1.005(3) 0.110(2) 0.170(18) Uani 0.34(3) 1 d P . . F15A F -0.086(3) 0.967(4) 0.055(4) 0.22(2) Uani 0.34(3) 1 d P . . C16 C 0.2199(5) 0.8910(2) 0.5256(3) 0.0518(10) Uani 1 1 d . . . C17 C 0.3013(5) 0.8208(3) 0.5804(4) 0.0680(12) Uani 1 1 d . . . H17A H 0.2522 0.7697 0.5576 0.080 Uiso 1 1 calc R . . C18 C 0.4569(6) 0.8272(4) 0.6695(5) 0.0901(16) Uani 1 1 d . . . H18A H 0.5131 0.7800 0.7078 0.080 Uiso 1 1 calc R . . C19 C 0.5289(6) 0.9022(4) 0.7019(5) 0.0981(17) Uani 1 1 d . . . H19A H 0.6337 0.9062 0.7626 0.080 Uiso 1 1 calc R . . C20 C 0.4475(7) 0.9710(3) 0.6456(5) 0.0994(17) Uani 1 1 d . . . H20A H 0.4973 1.0221 0.6674 0.080 Uiso 1 1 calc R . . C21 C 0.2917(5) 0.9658(3) 0.5563(4) 0.0757(13) Uani 1 1 d . . . H21A H 0.2365 1.0130 0.5175 0.080 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 0.052(2) 0.0524(19) 0.0462(19) 0.0018(16) 0.0130(16) 0.0031(17) N2 0.066(2) 0.056(2) 0.046(2) 0.0060(17) 0.0178(18) -0.0006(17) C3 0.061(3) 0.056(3) 0.045(2) 0.004(2) 0.010(2) 0.002(2) C4 0.061(3) 0.054(2) 0.050(2) -0.0004(19) 0.014(2) -0.006(2) C5 0.053(2) 0.046(2) 0.047(2) -0.0018(19) 0.014(2) 0.002(2) C6 0.050(2) 0.048(2) 0.047(2) 0.000(2) 0.0145(18) 0.0038(19) C7 0.070(3) 0.062(3) 0.055(3) 0.001(2) 0.017(2) -0.004(2) C8 0.076(3) 0.071(3) 0.077(3) 0.011(3) 0.024(3) -0.006(2) C9 0.067(3) 0.092(4) 0.069(3) 0.027(3) 0.032(2) 0.009(3) C10 0.066(3) 0.091(3) 0.049(2) -0.001(3) 0.021(2) 0.011(3) C11 0.061(3) 0.058(2) 0.057(3) -0.003(2) 0.021(2) -0.001(2) C12 0.086(4) 0.081(4) 0.060(4) 0.007(3) 0.009(4) -0.004(4) F13 0.076(6) 0.215(19) 0.099(7) 0.073(9) -0.010(4) -0.021(7) F14 0.178(12) 0.077(5) 0.071(5) 0.025(4) 0.000(6) -0.015(7) F15 0.188(12) 0.138(8) 0.046(4) 0.002(5) 0.042(4) 0.035(7) F13A 0.37(5) 0.16(2) 0.075(13) 0.053(13) -0.11(2) -0.12(3) F14A 0.21(4) 0.18(3) 0.126(14) 0.084(17) 0.06(2) 0.11(3) F15A 0.150(15) 0.35(5) 0.19(3) 0.20(3) 0.090(19) 0.05(3) C16 0.050(3) 0.059(3) 0.047(2) 0.000(2) 0.016(2) 0.004(2) C17 0.061(3) 0.070(3) 0.072(3) 0.015(2) 0.020(2) 0.010(2) C18 0.060(3) 0.118(5) 0.088(3) 0.033(3) 0.015(3) 0.021(3) C19 0.054(3) 0.153(6) 0.076(3) 0.003(4) 0.003(3) 0.002(4) C20 0.077(4) 0.099(4) 0.111(4) -0.027(3) 0.010(3) -0.012(3) C21 0.059(3) 0.073(3) 0.085(3) -0.014(2) 0.008(3) 0.002(2) _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 C5 1.362(4) . ? N1 N2 1.363(4) . ? N1 C16 1.438(4) . ? N2 C3 1.322(4) . ? C3 C4 1.381(5) . ? C3 C12 1.484(6) . ? C4 C5 1.374(5) . ? C5 C6 1.465(5) . ? C6 C7 1.378(5) . ? C6 C11 1.386(5) . ? C7 C8 1.376(5) . ? C8 C9 1.360(6) . ? C9 C10 1.379(6) . ? C10 C11 1.372(5) . ? C12 F13 1.296(11) . ? C12 F15A 1.26(2) . ? C12 F14A 1.27(2) . ? C12 F13A 1.26(2) . ? C12 F15 1.309(11) . ? C12 F14 1.304(10) . ? F13 F13A 0.96(6) . ? F13 F14A 1.33(4) . ? F14 F14A 1.03(4) . ? F14 F15A 1.27(5) . ? F15 F15A 1.05(6) . ? F15 F13A 1.42(6) . ? C16 C21 1.356(5) . ? C16 C17 1.372(5) . ? C17 C18 1.378(6) . ? C18 C19 1.362(7) . ? C19 C20 1.358(7) . ? C20 C21 1.379(6) . ? 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 N1 N2 112.5(3) . . ? C5 N1 C16 129.0(3) . . ? N2 N1 C16 118.3(3) . . ? C3 N2 N1 103.6(3) . . ? N2 C3 C4 112.8(3) . . ? N2 C3 C12 119.0(4) . . ? C4 C3 C12 128.1(4) . . ? C5 C4 C3 105.6(3) . . ? N1 C5 C4 105.5(3) . . ? N1 C5 C6 125.5(3) . . ? C4 C5 C6 128.7(4) . . ? C7 C6 C11 118.6(3) . . ? C7 C6 C5 119.9(3) . . ? C11 C6 C5 121.4(3) . . ? C8 C7 C6 121.0(4) . . ? C9 C8 C7 120.0(4) . . ? C8 C9 C10 120.0(4) . . ? C11 C10 C9 120.3(4) . . ? C10 C11 C6 120.2(4) . . ? F13 C12 F15A 130.7(16) . . ? F13 C12 F14A 62(2) . . ? F15A C12 F14A 102.0(16) . . ? F13 C12 F13A 44(3) . . ? F15A C12 F13A 109(2) . . ? F14A C12 F13A 103(2) . . ? F13 C12 F15 108.1(9) . . ? F15A C12 F15 48(3) . . ? F14A C12 F15 134.7(9) . . ? F13A C12 F15 67(3) . . ? F13 C12 F14 105.9(9) . . ? F15A C12 F14 60(2) . . ? F14A C12 F14 47(2) . . ? F13A C12 F14 133.4(13) . . ? F15 C12 F14 105.9(8) . . ? F13 C12 C3 112.2(7) . . ? F15A C12 C3 116.7(12) . . ? F14A C12 C3 113.4(10) . . ? F13A C12 C3 111.7(12) . . ? F15 C12 C3 111.0(6) . . ? F14 C12 C3 113.4(5) . . ? F13A F13 C12 66(2) . . ? F13A F13 F14A 119(3) . . ? C12 F13 F14A 58.2(12) . . ? F14A F14 C12 64.9(16) . . ? F14A F14 F15A 117(2) . . ? C12 F14 F15A 58.5(15) . . ? F15A F15 C12 63.5(19) . . ? F15A F15 F13A 111(2) . . ? C12 F15 F13A 54.5(16) . . ? F13 F13A C12 70(2) . . ? F13 F13A F15 123(3) . . ? C12 F13A F15 58(2) . . ? F14 F14A C12 67.9(18) . . ? F14 F14A F13 122(2) . . ? C12 F14A F13 59.7(16) . . ? F15 F15A C12 68(2) . . ? F15 F15A F14 127(3) . . ? C12 F15A F14 61.9(17) . . ? C21 C16 C17 120.9(4) . . ? C21 C16 N1 118.7(4) . . ? C17 C16 N1 120.3(4) . . ? C16 C17 C18 119.1(4) . . ? C19 C18 C17 120.3(5) . . ? C20 C19 C18 119.9(5) . . ? C19 C20 C21 120.6(5) . . ? C16 C21 C20 119.2(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 50.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.144 _refine_diff_density_min -0.107 _refine_diff_density_rms 0.033