# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Ian R Baxendale' _publ_contact_author_email IRB21@CAM.AC.UK _publ_section_title ; The Application of Flow Microreactors to the Preparation of a Family of Casein Kinase I Inhibitors ; loop_ _publ_author_name 'Ian R Baxendale' 'Steven Ley' 'Nikzad Nikbin' 'Francesco Venturoni' # Attachment 'sl0928.cif' data_sl0928 _database_code_depnum_ccdc_archive 'CCDC 756493' #TrackingRef 'sl0928.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 F N5' _chemical_formula_sum 'C22 H20 F N5' _chemical_formula_weight 373.43 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0627(4) _cell_length_b 10.2605(6) _cell_length_c 15.1321(11) _cell_angle_alpha 101.825(3) _cell_angle_beta 97.542(3) _cell_angle_gamma 98.935(4) _cell_volume 897.12(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23251 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 1.001 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6928 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0575 _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 -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3170 _reflns_number_gt 2321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.7255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3170 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 F1 F 0.0741(3) 0.85086(18) 0.91019(12) 0.0448(5) Uani 1 1 d . . . N1 N 0.8939(3) 1.3153(2) 0.90310(15) 0.0277(5) Uani 1 1 d . . . N2 N 1.1045(3) 1.2909(2) 0.79288(14) 0.0236(5) Uani 1 1 d . . . N3 N 1.2673(3) 1.3201(2) 0.74153(14) 0.0251(5) Uani 1 1 d . . . N4 N 0.7194(3) 1.0234(2) 0.63210(15) 0.0282(5) Uani 1 1 d . . . N5 N 1.5958(4) 1.4589(2) 0.73171(15) 0.0281(5) Uani 1 1 d . . . C1 C 0.8076(4) 1.1959(3) 0.83987(17) 0.0240(6) Uani 1 1 d . . . C2 C 0.9328(4) 1.1781(3) 0.76905(17) 0.0233(6) Uani 1 1 d . . . C3 C 1.4216(4) 1.4304(3) 0.78036(17) 0.0245(6) Uani 1 1 d . . . C4 C 1.4146(4) 1.5163(3) 0.86686(18) 0.0290(6) Uani 1 1 d . . . H4 H 1.5325 1.5924 0.8929 0.035 Uiso 1 1 calc R . . C5 C 1.2388(4) 1.4889(3) 0.91177(18) 0.0289(6) Uani 1 1 d . . . H5 H 1.2274 1.5478 0.9676 0.035 Uiso 1 1 calc R . . C6 C 1.0743(4) 1.3711(3) 0.87339(17) 0.0249(6) Uani 1 1 d . . . C7 C 0.6138(4) 1.1026(3) 0.85628(17) 0.0242(6) Uani 1 1 d . . . C8 C 0.4609(4) 1.1556(3) 0.90835(18) 0.0274(6) Uani 1 1 d . . . H8 H 0.4823 1.2508 0.9315 0.033 Uiso 1 1 calc R . . C9 C 0.2783(4) 1.0719(3) 0.92699(18) 0.0308(7) Uani 1 1 d . . . H9 H 0.1737 1.1084 0.9619 0.037 Uiso 1 1 calc R . . C10 C 0.2537(4) 0.9349(3) 0.89338(18) 0.0301(6) Uani 1 1 d . . . C11 C 0.4019(4) 0.8780(3) 0.84353(19) 0.0311(6) Uani 1 1 d . . . H11 H 0.3808 0.7824 0.8221 0.037 Uiso 1 1 calc R . . C12 C 0.5826(4) 0.9622(3) 0.82510(18) 0.0282(6) Uani 1 1 d . . . H12 H 0.6868 0.9241 0.7908 0.034 Uiso 1 1 calc R . . C13 C 0.9214(4) 1.0693(2) 0.68759(17) 0.0220(6) Uani 1 1 d . . . C14 C 1.1129(4) 1.0149(3) 0.67160(17) 0.0261(6) Uani 1 1 d . . . H14 H 1.2536 1.0504 0.7115 0.031 Uiso 1 1 calc R . . C15 C 1.0954(4) 0.9085(3) 0.59696(18) 0.0291(6) Uani 1 1 d . . . H15 H 1.2233 0.8688 0.5854 0.035 Uiso 1 1 calc R . . C16 C 0.8902(4) 0.8606(3) 0.53935(18) 0.0293(6) Uani 1 1 d . . . H16 H 0.8735 0.7878 0.4873 0.035 Uiso 1 1 calc R . . C17 C 0.7096(4) 0.9217(3) 0.55965(18) 0.0308(6) Uani 1 1 d . . . H17 H 0.5688 0.8893 0.5194 0.037 Uiso 1 1 calc R . . C18 C 1.6949(5) 1.6007(3) 0.7394(2) 0.0417(8) Uani 1 1 d . . . H18A H 1.7204 1.6498 0.8045 0.050 Uiso 1 1 calc R . . H18B H 1.5865 1.6424 0.7046 0.050 Uiso 1 1 calc R . . C19 C 1.9146(5) 1.6168(3) 0.7042(2) 0.0423(8) Uani 1 1 d . . . H19A H 2.0295 1.5867 0.7442 0.051 Uiso 1 1 calc R . . H19B H 1.9682 1.7138 0.7065 0.051 Uiso 1 1 calc R . . C20 C 1.8911(5) 1.5359(3) 0.6074(2) 0.0408(8) Uani 1 1 d . . . H20A H 2.0417 1.5420 0.5882 0.049 Uiso 1 1 calc R . . H20B H 1.7923 1.5737 0.5657 0.049 Uiso 1 1 calc R . . C21 C 1.7902(5) 1.3889(3) 0.6007(2) 0.0393(7) Uani 1 1 d . . . H21A H 1.7597 1.3395 0.5356 0.047 Uiso 1 1 calc R . . H21B H 1.9018 1.3476 0.6341 0.047 Uiso 1 1 calc R . . C22 C 1.5730(4) 1.3728(3) 0.63963(19) 0.0319(7) Uani 1 1 d . . . H22A H 1.4518 1.3959 0.5984 0.038 Uiso 1 1 calc R . . H22B H 1.5272 1.2768 0.6420 0.038 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 F1 0.0323(9) 0.0477(11) 0.0547(11) 0.0135(9) 0.0187(8) -0.0035(8) N1 0.0263(11) 0.0270(12) 0.0271(12) -0.0003(10) 0.0067(9) 0.0035(9) N2 0.0229(11) 0.0247(12) 0.0215(11) 0.0008(9) 0.0066(9) 0.0026(9) N3 0.0230(11) 0.0251(12) 0.0259(12) 0.0020(10) 0.0087(9) 0.0015(9) N4 0.0236(11) 0.0298(13) 0.0270(12) -0.0015(10) 0.0045(9) 0.0024(9) N5 0.0297(12) 0.0228(12) 0.0277(12) -0.0006(10) 0.0099(9) -0.0031(9) C1 0.0221(13) 0.0241(14) 0.0240(13) 0.0016(11) 0.0021(10) 0.0055(10) C2 0.0211(13) 0.0226(14) 0.0235(13) 0.0011(11) 0.0040(10) 0.0013(10) C3 0.0245(13) 0.0225(14) 0.0254(14) 0.0029(11) 0.0051(11) 0.0037(11) C4 0.0303(14) 0.0254(15) 0.0262(14) 0.0000(12) 0.0043(11) -0.0024(11) C5 0.0332(15) 0.0272(15) 0.0228(14) -0.0006(12) 0.0047(11) 0.0040(12) C6 0.0262(13) 0.0253(14) 0.0215(13) 0.0003(11) 0.0062(10) 0.0047(11) C7 0.0203(12) 0.0298(15) 0.0222(13) 0.0057(11) 0.0029(10) 0.0050(11) C8 0.0238(13) 0.0313(15) 0.0261(14) 0.0040(12) 0.0043(11) 0.0056(11) C9 0.0247(14) 0.0425(18) 0.0259(15) 0.0053(13) 0.0086(11) 0.0078(12) C10 0.0216(13) 0.0385(17) 0.0300(15) 0.0101(13) 0.0063(11) 0.0000(12) C11 0.0304(15) 0.0262(15) 0.0352(16) 0.0066(13) 0.0054(12) 0.0014(12) C12 0.0251(13) 0.0296(15) 0.0314(15) 0.0058(12) 0.0096(11) 0.0069(11) C13 0.0235(13) 0.0193(13) 0.0220(13) 0.0027(11) 0.0050(10) 0.0021(10) C14 0.0214(13) 0.0278(15) 0.0268(14) 0.0030(12) 0.0033(10) 0.0028(11) C15 0.0289(14) 0.0279(15) 0.0314(15) 0.0022(12) 0.0111(11) 0.0092(11) C16 0.0335(15) 0.0239(15) 0.0270(15) -0.0012(12) 0.0077(11) 0.0024(11) C17 0.0253(14) 0.0316(16) 0.0283(15) -0.0030(13) 0.0019(11) -0.0008(11) C18 0.0469(18) 0.0289(16) 0.0445(18) -0.0028(14) 0.0207(15) -0.0036(13) C19 0.0406(17) 0.0392(18) 0.0412(18) 0.0023(15) 0.0146(14) -0.0074(14) C20 0.0455(18) 0.0378(18) 0.0376(17) 0.0064(14) 0.0164(14) -0.0013(14) C21 0.0400(17) 0.0419(18) 0.0353(17) 0.0039(14) 0.0160(13) 0.0042(14) C22 0.0328(15) 0.0302(16) 0.0288(15) -0.0016(12) 0.0107(12) 0.0005(12) _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 F1 C10 1.366(3) . ? N1 C6 1.329(3) . ? N1 C1 1.370(3) . ? N2 N3 1.369(3) . ? N2 C6 1.375(3) . ? N2 C2 1.381(3) . ? N3 C3 1.325(3) . ? N4 C17 1.337(3) . ? N4 C13 1.348(3) . ? N5 C3 1.392(3) . ? N5 C18 1.460(4) . ? N5 C22 1.466(3) . ? C1 C2 1.391(3) . ? C1 C7 1.478(4) . ? C2 C13 1.470(3) . ? C3 C4 1.430(4) . ? C4 C5 1.361(4) . ? C4 H4 0.9500 . ? C5 C6 1.407(4) . ? C5 H5 0.9500 . ? C7 C12 1.395(4) . ? C7 C8 1.396(3) . ? C8 C9 1.389(4) . ? C8 H8 0.9500 . ? C9 C10 1.370(4) . ? C9 H9 0.9500 . ? C10 C11 1.371(4) . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.392(3) . ? C14 C15 1.380(4) . ? C14 H14 0.9500 . ? C15 C16 1.378(4) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.497(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.505(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.514(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.511(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 C1 105.4(2) . . ? N3 N2 C6 126.5(2) . . ? N3 N2 C2 125.2(2) . . ? C6 N2 C2 108.2(2) . . ? C3 N3 N2 114.5(2) . . ? C17 N4 C13 116.8(2) . . ? C3 N5 C18 118.2(2) . . ? C3 N5 C22 116.3(2) . . ? C18 N5 C22 114.0(2) . . ? N1 C1 C2 111.5(2) . . ? N1 C1 C7 119.3(2) . . ? C2 C1 C7 129.0(2) . . ? N2 C2 C1 103.9(2) . . ? N2 C2 C13 121.8(2) . . ? C1 C2 C13 134.2(2) . . ? N3 C3 N5 115.8(2) . . ? N3 C3 C4 123.3(2) . . ? N5 C3 C4 121.0(2) . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 118.3(2) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? N1 C6 N2 110.9(2) . . ? N1 C6 C5 131.8(2) . . ? N2 C6 C5 117.1(2) . . ? C12 C7 C8 118.3(2) . . ? C12 C7 C1 122.5(2) . . ? C8 C7 C1 119.1(2) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 117.9(2) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? F1 C10 C9 118.9(2) . . ? F1 C10 C11 118.2(3) . . ? C9 C10 C11 122.9(2) . . ? C10 C11 C12 118.7(3) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C11 C12 C7 120.8(2) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? N4 C13 C14 122.5(2) . . ? N4 C13 C2 117.4(2) . . ? C14 C13 C2 120.1(2) . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 119.3(2) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 117.9(2) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? N4 C17 C16 124.5(2) . . ? N4 C17 H17 117.8 . . ? C16 C17 H17 117.8 . . ? N5 C18 C19 112.5(2) . . ? N5 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? N5 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C18 C19 C20 111.8(2) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 110.1(2) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 112.6(2) . . ? C22 C21 H21A 109.1 . . ? C20 C21 H21A 109.1 . . ? C22 C21 H21B 109.1 . . ? C20 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? N5 C22 C21 112.5(2) . . ? N5 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? N5 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? 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 C6 N2 N3 C3 7.5(4) . . . . ? C2 N2 N3 C3 -176.7(2) . . . . ? C6 N1 C1 C2 -1.1(3) . . . . ? C6 N1 C1 C7 175.3(2) . . . . ? N3 N2 C2 C1 -177.7(2) . . . . ? C6 N2 C2 C1 -1.2(3) . . . . ? N3 N2 C2 C13 5.8(4) . . . . ? C6 N2 C2 C13 -177.7(2) . . . . ? N1 C1 C2 N2 1.5(3) . . . . ? C7 C1 C2 N2 -174.5(2) . . . . ? N1 C1 C2 C13 177.3(3) . . . . ? C7 C1 C2 C13 1.3(5) . . . . ? N2 N3 C3 N5 176.9(2) . . . . ? N2 N3 C3 C4 -2.8(4) . . . . ? C18 N5 C3 N3 147.8(3) . . . . ? C22 N5 C3 N3 6.7(3) . . . . ? C18 N5 C3 C4 -32.4(4) . . . . ? C22 N5 C3 C4 -173.6(3) . . . . ? N3 C3 C4 C5 -2.4(4) . . . . ? N5 C3 C4 C5 177.9(2) . . . . ? C3 C4 C5 C6 3.5(4) . . . . ? C1 N1 C6 N2 0.3(3) . . . . ? C1 N1 C6 C5 -175.5(3) . . . . ? N3 N2 C6 N1 177.0(2) . . . . ? C2 N2 C6 N1 0.6(3) . . . . ? N3 N2 C6 C5 -6.5(4) . . . . ? C2 N2 C6 C5 177.1(2) . . . . ? C4 C5 C6 N1 176.1(3) . . . . ? C4 C5 C6 N2 0.5(4) . . . . ? N1 C1 C7 C12 -148.7(3) . . . . ? C2 C1 C7 C12 27.0(4) . . . . ? N1 C1 C7 C8 28.4(4) . . . . ? C2 C1 C7 C8 -156.0(3) . . . . ? C12 C7 C8 C9 -1.7(4) . . . . ? C1 C7 C8 C9 -178.9(2) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C9 C10 F1 -179.4(2) . . . . ? C8 C9 C10 C11 0.7(4) . . . . ? F1 C10 C11 C12 179.2(2) . . . . ? C9 C10 C11 C12 -1.0(4) . . . . ? C10 C11 C12 C7 -0.2(4) . . . . ? C8 C7 C12 C11 1.5(4) . . . . ? C1 C7 C12 C11 178.5(2) . . . . ? C17 N4 C13 C14 -0.1(4) . . . . ? C17 N4 C13 C2 -178.1(2) . . . . ? N2 C2 C13 N4 -133.6(3) . . . . ? C1 C2 C13 N4 51.2(4) . . . . ? N2 C2 C13 C14 48.3(4) . . . . ? C1 C2 C13 C14 -126.9(3) . . . . ? N4 C13 C14 C15 -1.0(4) . . . . ? C2 C13 C14 C15 177.0(2) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C13 N4 C17 C16 1.0(4) . . . . ? C15 C16 C17 N4 -0.8(4) . . . . ? C3 N5 C18 C19 165.5(2) . . . . ? C22 N5 C18 C19 -52.5(3) . . . . ? N5 C18 C19 C20 54.6(4) . . . . ? C18 C19 C20 C21 -54.1(4) . . . . ? C19 C20 C21 C22 52.3(4) . . . . ? C3 N5 C22 C21 -167.0(2) . . . . ? C18 N5 C22 C21 50.3(3) . . . . ? C20 C21 C22 N5 -50.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.240 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.056 # Attachment 'sl0933.cif' data_sl0933 _database_code_depnum_ccdc_archive 'CCDC 756494' #TrackingRef 'sl0933.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H10 Cl F N4' _chemical_formula_sum 'C17 H10 Cl F N4' _chemical_formula_weight 324.74 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' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 '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 11.6203(2) _cell_length_b 7.1518(2) _cell_length_c 17.4558(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.360(1) _cell_angle_gamma 90.00 _cell_volume 1431.37(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9491 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15512 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3399 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.6593P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3399 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Cl1 Cl 0.37135(4) 0.63603(7) -0.00524(3) 0.04673(14) Uani 1 1 d . . . F1 F -0.50624(10) 0.80287(17) 0.21387(7) 0.0607(3) Uani 1 1 d . . . N1 N -0.11171(11) 0.7806(2) 0.00110(8) 0.0349(3) Uani 1 1 d . . . N2 N 0.07432(11) 0.72753(18) 0.05374(7) 0.0299(3) Uani 1 1 d . . . N3 N 0.19082(11) 0.69425(19) 0.05899(8) 0.0328(3) Uani 1 1 d . . . N4 N 0.02230(12) 0.8605(2) 0.24310(8) 0.0368(3) Uani 1 1 d . . . C1 C -0.10123(13) 0.7722(2) 0.08053(9) 0.0310(3) Uani 1 1 d . . . C2 C 0.01411(13) 0.7434(2) 0.11544(9) 0.0293(3) Uani 1 1 d . . . C3 C 0.22447(14) 0.6829(2) -0.00862(10) 0.0346(4) Uani 1 1 d . . . C4 C 0.15448(15) 0.7072(2) -0.08210(10) 0.0380(4) Uani 1 1 d . . . H4 H 0.1872 0.6982 -0.1284 0.046 Uiso 1 1 calc R . . C5 C 0.03921(15) 0.7438(2) -0.08477(10) 0.0376(4) Uani 1 1 d . . . H5 H -0.0104 0.7629 -0.1330 0.045 Uiso 1 1 calc R . . C6 C -0.00492(14) 0.7528(2) -0.01444(9) 0.0334(4) Uani 1 1 d . . . C7 C -0.20666(13) 0.7818(2) 0.11702(9) 0.0307(3) Uani 1 1 d . . . C8 C -0.30247(14) 0.8868(2) 0.08245(10) 0.0353(4) Uani 1 1 d . . . H8 H -0.2986 0.9527 0.0357 0.042 Uiso 1 1 calc R . . C9 C -0.40301(15) 0.8965(3) 0.11522(11) 0.0417(4) Uani 1 1 d . . . H9 H -0.4669 0.9720 0.0927 0.050 Uiso 1 1 calc R . . C10 C -0.40805(15) 0.7941(3) 0.18122(11) 0.0408(4) Uani 1 1 d . . . C11 C -0.31813(15) 0.6818(2) 0.21541(10) 0.0386(4) Uani 1 1 d . . . H11 H -0.3255 0.6081 0.2596 0.046 Uiso 1 1 calc R . . C12 C -0.21660(14) 0.6794(2) 0.18356(9) 0.0342(4) Uani 1 1 d . . . H12 H -0.1524 0.6065 0.2075 0.041 Uiso 1 1 calc R . . C13 C 0.06922(13) 0.7405(2) 0.19741(9) 0.0298(3) Uani 1 1 d . . . C14 C 0.16154(14) 0.6232(2) 0.22585(10) 0.0375(4) Uani 1 1 d . . . H14 H 0.1936 0.5408 0.1922 0.045 Uiso 1 1 calc R . . C15 C 0.20598(15) 0.6288(3) 0.30450(10) 0.0426(4) Uani 1 1 d . . . H15 H 0.2689 0.5496 0.3255 0.051 Uiso 1 1 calc R . . C16 C 0.15849(14) 0.7497(3) 0.35185(10) 0.0395(4) Uani 1 1 d . . . H16 H 0.1877 0.7564 0.4059 0.047 Uiso 1 1 calc R . . C17 C 0.06698(15) 0.8611(3) 0.31852(10) 0.0413(4) Uani 1 1 d . . . H17 H 0.0336 0.9437 0.3514 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0409(2) 0.0540(3) 0.0478(3) 0.0075(2) 0.01463(19) 0.0074(2) F1 0.0530(7) 0.0594(7) 0.0774(8) -0.0034(6) 0.0335(6) 0.0069(6) N1 0.0346(7) 0.0381(8) 0.0303(7) -0.0022(6) 0.0002(6) -0.0040(6) N2 0.0319(6) 0.0286(7) 0.0284(7) -0.0011(5) 0.0025(5) -0.0026(5) N3 0.0321(7) 0.0329(7) 0.0334(7) 0.0011(6) 0.0056(6) -0.0007(6) N4 0.0361(7) 0.0419(8) 0.0300(7) -0.0056(6) -0.0018(6) 0.0043(6) C1 0.0339(8) 0.0282(8) 0.0291(8) -0.0010(6) 0.0001(6) -0.0042(6) C2 0.0319(8) 0.0266(7) 0.0289(8) -0.0009(6) 0.0038(6) -0.0017(6) C3 0.0384(9) 0.0288(8) 0.0374(9) 0.0005(7) 0.0085(7) -0.0024(7) C4 0.0502(10) 0.0337(9) 0.0312(9) -0.0023(7) 0.0099(7) -0.0033(8) C5 0.0452(9) 0.0383(9) 0.0281(8) -0.0025(7) 0.0019(7) -0.0056(8) C6 0.0372(8) 0.0321(8) 0.0289(8) -0.0022(7) -0.0006(7) -0.0053(7) C7 0.0313(8) 0.0282(8) 0.0309(8) -0.0043(6) 0.0002(6) -0.0037(6) C8 0.0356(8) 0.0315(8) 0.0369(9) -0.0005(7) 0.0000(7) -0.0025(7) C9 0.0348(9) 0.0364(9) 0.0521(11) -0.0040(8) 0.0019(8) 0.0029(7) C10 0.0379(9) 0.0381(9) 0.0490(10) -0.0114(8) 0.0151(8) -0.0031(7) C11 0.0464(9) 0.0354(9) 0.0354(9) -0.0051(7) 0.0108(7) -0.0037(8) C12 0.0366(8) 0.0320(8) 0.0325(8) -0.0022(7) 0.0018(7) -0.0010(7) C13 0.0300(7) 0.0303(8) 0.0282(8) 0.0013(6) 0.0018(6) -0.0038(6) C14 0.0379(9) 0.0382(9) 0.0365(9) 0.0029(7) 0.0060(7) 0.0057(7) C15 0.0362(9) 0.0472(10) 0.0413(10) 0.0105(8) -0.0032(7) 0.0062(8) C16 0.0370(9) 0.0486(10) 0.0297(8) 0.0033(8) -0.0040(7) -0.0049(8) C17 0.0425(9) 0.0489(11) 0.0301(9) -0.0076(8) -0.0012(7) 0.0030(8) _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 Cl1 C3 1.7309(17) . ? F1 C10 1.3572(19) . ? N1 C6 1.328(2) . ? N1 C1 1.373(2) . ? N2 N3 1.3629(17) . ? N2 C2 1.381(2) . ? N2 C6 1.3930(19) . ? N3 C3 1.305(2) . ? N4 C17 1.334(2) . ? N4 C13 1.346(2) . ? C1 C2 1.394(2) . ? C1 C7 1.471(2) . ? C2 C13 1.470(2) . ? C3 C4 1.413(2) . ? C4 C5 1.358(2) . ? C4 H4 0.9500 . ? C5 C6 1.407(2) . ? C5 H5 0.9500 . ? C7 C12 1.394(2) . ? C7 C8 1.396(2) . ? C8 C9 1.384(2) . ? C8 H8 0.9500 . ? C9 C10 1.374(3) . ? C9 H9 0.9500 . ? C10 C11 1.375(3) . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.389(2) . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 C16 1.372(3) . ? C15 H15 0.9500 . ? C16 C17 1.379(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C1 105.51(13) . . ? N3 N2 C2 125.84(12) . . ? N3 N2 C6 126.26(13) . . ? C2 N2 C6 107.89(13) . . ? C3 N3 N2 112.99(13) . . ? C17 N4 C13 117.18(14) . . ? N1 C1 C2 111.64(14) . . ? N1 C1 C7 119.45(13) . . ? C2 C1 C7 128.79(14) . . ? N2 C2 C1 104.13(13) . . ? N2 C2 C13 124.21(13) . . ? C1 C2 C13 131.55(15) . . ? N3 C3 C4 126.89(16) . . ? N3 C3 Cl1 114.85(12) . . ? C4 C3 Cl1 118.26(13) . . ? C5 C4 C3 118.28(16) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 118.44(16) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? N1 C6 N2 110.78(13) . . ? N1 C6 C5 132.12(15) . . ? N2 C6 C5 117.09(15) . . ? C12 C7 C8 118.32(15) . . ? C12 C7 C1 121.60(14) . . ? C8 C7 C1 119.97(15) . . ? C9 C8 C7 121.06(16) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 C8 118.28(16) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? F1 C10 C9 118.73(16) . . ? F1 C10 C11 118.44(17) . . ? C9 C10 C11 122.83(16) . . ? C10 C11 C12 118.06(16) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? C11 C12 C7 121.33(15) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? N4 C13 C14 122.49(14) . . ? N4 C13 C2 114.44(13) . . ? C14 C13 C2 123.06(15) . . ? C15 C14 C13 118.56(16) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 119.56(16) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 117.88(16) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? N4 C17 C16 124.32(17) . . ? N4 C17 H17 117.8 . . ? C16 C17 H17 117.8 . . ? 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 C2 N2 N3 C3 178.93(15) . . . . ? C6 N2 N3 C3 -1.5(2) . . . . ? C6 N1 C1 C2 1.49(18) . . . . ? C6 N1 C1 C7 -174.85(14) . . . . ? N3 N2 C2 C1 -178.58(14) . . . . ? C6 N2 C2 C1 1.82(16) . . . . ? N3 N2 C2 C13 4.8(2) . . . . ? C6 N2 C2 C13 -174.79(15) . . . . ? N1 C1 C2 N2 -2.08(18) . . . . ? C7 C1 C2 N2 173.83(15) . . . . ? N1 C1 C2 C13 174.17(16) . . . . ? C7 C1 C2 C13 -9.9(3) . . . . ? N2 N3 C3 C4 2.2(2) . . . . ? N2 N3 C3 Cl1 -178.76(10) . . . . ? N3 C3 C4 C5 -1.0(3) . . . . ? Cl1 C3 C4 C5 179.95(13) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C1 N1 C6 N2 -0.27(18) . . . . ? C1 N1 C6 C5 179.24(18) . . . . ? N3 N2 C6 N1 179.38(14) . . . . ? C2 N2 C6 N1 -1.02(18) . . . . ? N3 N2 C6 C5 -0.2(2) . . . . ? C2 N2 C6 C5 179.38(14) . . . . ? C4 C5 C6 N1 -178.01(17) . . . . ? C4 C5 C6 N2 1.5(2) . . . . ? N1 C1 C7 C12 144.13(16) . . . . ? C2 C1 C7 C12 -31.5(2) . . . . ? N1 C1 C7 C8 -32.1(2) . . . . ? C2 C1 C7 C8 152.26(16) . . . . ? C12 C7 C8 C9 3.0(2) . . . . ? C1 C7 C8 C9 179.35(15) . . . . ? C7 C8 C9 C10 -2.5(2) . . . . ? C8 C9 C10 F1 179.91(15) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? F1 C10 C11 C12 -177.48(15) . . . . ? C9 C10 C11 C12 3.0(3) . . . . ? C10 C11 C12 C7 -2.4(2) . . . . ? C8 C7 C12 C11 -0.5(2) . . . . ? C1 C7 C12 C11 -176.76(15) . . . . ? C17 N4 C13 C14 -1.1(2) . . . . ? C17 N4 C13 C2 178.49(15) . . . . ? N2 C2 C13 N4 141.29(15) . . . . ? C1 C2 C13 N4 -34.3(2) . . . . ? N2 C2 C13 C14 -39.1(2) . . . . ? C1 C2 C13 C14 145.26(18) . . . . ? N4 C13 C14 C15 0.7(3) . . . . ? C2 C13 C14 C15 -178.82(16) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C13 N4 C17 C16 1.1(3) . . . . ? C15 C16 C17 N4 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.212 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.045 # Attachment 'sl0941.cif' data_sl0941 _database_code_depnum_ccdc_archive 'CCDC 756495' #TrackingRef 'sl0941.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 Br F N O 1+, Br 1-' _chemical_formula_sum 'C13 H10 Br2 F N O' _chemical_formula_weight 375.04 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8896(2) _cell_length_b 8.2318(2) _cell_length_c 12.0308(3) _cell_angle_alpha 83.177(1) _cell_angle_beta 85.689(1) _cell_angle_gamma 61.994(1) _cell_volume 684.80(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7555 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 5.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.462 _exptl_absorpt_correction_T_max 0.821 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -NH hydrogen atom was NOT located in the final difference map. The position of this H atom is shrouded in doubt (JED). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9948 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 32.03 _reflns_number_total 4729 _reflns_number_gt 4002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.8954P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4729 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Br1 Br 0.22350(4) 0.00492(4) -0.11772(2) 0.02908(9) Uani 1 1 d . . . Br2 Br 0.17430(4) 0.19522(4) 0.13589(3) 0.03022(9) Uani 1 1 d . . . O1 O 0.2102(4) -0.1806(4) -0.3744(2) 0.0410(6) Uani 1 1 d . . . N1 N 0.2754(3) -0.3976(3) -0.1587(2) 0.0246(4) Uani 1 1 d . . . H1 H 0.1579 -0.3070 -0.1678 0.030 Uiso 1 1 calc R . . F1 F 0.2712(4) 0.5313(3) -0.5806(2) 0.0514(6) Uani 1 1 d . . . C1 C 0.2767(5) 0.3779(4) -0.5213(3) 0.0354(6) Uani 1 1 d . . . C2 C 0.3881(5) 0.3061(5) -0.4283(3) 0.0360(7) Uani 1 1 d . . . H2 H 0.4604 0.3616 -0.4060 0.043 Uiso 1 1 calc R . . C3 C 0.3924(5) 0.1494(4) -0.3673(3) 0.0305(6) Uani 1 1 d . . . H3 H 0.4680 0.0969 -0.3023 0.037 Uiso 1 1 calc R . . C4 C 0.2858(4) 0.0690(4) -0.4015(2) 0.0260(5) Uani 1 1 d . . . C5 C 0.1776(4) 0.1455(4) -0.4980(3) 0.0323(6) Uani 1 1 d . . . H5 H 0.1063 0.0903 -0.5221 0.039 Uiso 1 1 calc R . . C6 C 0.1728(5) 0.3011(5) -0.5590(3) 0.0370(7) Uani 1 1 d . . . H6 H 0.0998 0.3532 -0.6250 0.044 Uiso 1 1 calc R . . C7 C 0.2861(4) -0.0983(4) -0.3399(2) 0.0260(5) Uani 1 1 d . . . C8 C 0.3855(4) -0.1679(4) -0.2265(2) 0.0237(5) Uani 1 1 d . . . H8 H 0.5112 -0.1651 -0.2345 0.028 Uiso 1 1 calc R . . C9 C 0.4231(4) -0.3597(4) -0.1846(2) 0.0220(4) Uani 1 1 d . . . C10 C 0.6078(4) -0.5029(4) -0.1723(3) 0.0280(5) Uani 1 1 d . . . H10 H 0.7148 -0.4801 -0.1890 0.034 Uiso 1 1 calc R . . C11 C 0.6365(4) -0.6808(4) -0.1352(3) 0.0315(6) Uani 1 1 d . . . H11 H 0.7632 -0.7801 -0.1283 0.038 Uiso 1 1 calc R . . C12 C 0.4799(4) -0.7123(4) -0.1084(3) 0.0298(5) Uani 1 1 d . . . H12 H 0.4975 -0.8328 -0.0826 0.036 Uiso 1 1 calc R . . C13 C 0.2979(4) -0.5654(4) -0.1199(3) 0.0282(5) Uani 1 1 d . . . H13 H 0.1886 -0.5835 -0.1003 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03285(15) 0.02467(14) 0.03137(15) -0.00488(10) 0.00196(11) -0.01461(11) Br2 0.01826(13) 0.03027(15) 0.04265(18) -0.00866(12) 0.00007(10) -0.01067(11) O1 0.0556(15) 0.0452(13) 0.0398(12) 0.0036(10) -0.0169(11) -0.0375(13) N1 0.0177(9) 0.0234(10) 0.0326(11) -0.0029(8) -0.0018(8) -0.0092(8) F1 0.0700(16) 0.0383(11) 0.0456(12) 0.0114(9) 0.0020(11) -0.0290(11) C1 0.0427(16) 0.0275(13) 0.0316(14) 0.0036(11) 0.0058(12) -0.0150(12) C2 0.0447(17) 0.0347(15) 0.0365(15) 0.0002(12) 0.0014(13) -0.0261(14) C3 0.0349(14) 0.0324(14) 0.0296(13) 0.0000(11) -0.0027(11) -0.0207(12) C4 0.0259(12) 0.0262(12) 0.0266(12) -0.0011(9) -0.0008(9) -0.0129(10) C5 0.0318(14) 0.0324(14) 0.0323(14) 0.0017(11) -0.0082(11) -0.0146(11) C6 0.0387(16) 0.0340(15) 0.0318(14) 0.0038(12) -0.0039(12) -0.0127(13) C7 0.0253(12) 0.0282(12) 0.0279(12) -0.0006(10) -0.0039(9) -0.0152(10) C8 0.0214(10) 0.0235(11) 0.0283(12) 0.0000(9) -0.0033(9) -0.0124(9) C9 0.0189(10) 0.0228(11) 0.0253(11) -0.0029(9) -0.0007(8) -0.0102(9) C10 0.0195(11) 0.0288(12) 0.0358(14) -0.0018(10) -0.0027(10) -0.0114(10) C11 0.0233(12) 0.0254(12) 0.0418(16) -0.0020(11) -0.0032(11) -0.0078(10) C12 0.0277(13) 0.0224(11) 0.0381(15) -0.0014(10) -0.0050(11) -0.0104(10) C13 0.0253(12) 0.0246(12) 0.0374(14) -0.0012(10) -0.0020(10) -0.0141(10) _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 Br1 C8 1.963(3) . ? O1 C7 1.214(3) . ? N1 C13 1.337(3) . ? N1 C9 1.347(3) . ? N1 H1 0.8800 . ? F1 C1 1.358(3) . ? C1 C2 1.370(5) . ? C1 C6 1.374(5) . ? C2 C3 1.394(4) . ? C2 H2 0.9500 . ? C3 C4 1.397(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(4) . ? C4 C7 1.484(4) . ? C5 C6 1.384(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.536(4) . ? C8 C9 1.493(4) . ? C8 H8 1.0000 . ? C9 C10 1.383(4) . ? C10 C11 1.394(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 N1 C9 123.5(2) . . ? C13 N1 H1 118.3 . . ? C9 N1 H1 118.3 . . ? F1 C1 C2 118.3(3) . . ? F1 C1 C6 118.2(3) . . ? C2 C1 C6 123.5(3) . . ? C1 C2 C3 118.1(3) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 C7 118.2(3) . . ? C3 C4 C7 122.3(3) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 118.1(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? O1 C7 C4 123.2(3) . . ? O1 C7 C8 118.9(3) . . ? C4 C7 C8 117.9(2) . . ? C9 C8 C7 114.1(2) . . ? C9 C8 Br1 109.94(18) . . ? C7 C8 Br1 107.84(18) . . ? C9 C8 H8 108.3 . . ? C7 C8 H8 108.3 . . ? Br1 C8 H8 108.3 . . ? N1 C9 C10 118.2(2) . . ? N1 C9 C8 120.1(2) . . ? C10 C9 C8 121.7(2) . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 118.7(3) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? N1 C13 C12 119.9(3) . . ? N1 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? 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 F1 C1 C2 C3 179.6(3) . . . . ? C6 C1 C2 C3 -1.6(5) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C2 C3 C4 C7 179.7(3) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C7 C4 C5 C6 -179.7(3) . . . . ? F1 C1 C6 C5 -179.6(3) . . . . ? C2 C1 C6 C5 1.6(5) . . . . ? C4 C5 C6 C1 -0.4(5) . . . . ? C5 C4 C7 O1 6.4(5) . . . . ? C3 C4 C7 O1 -172.4(3) . . . . ? C5 C4 C7 C8 -172.8(3) . . . . ? C3 C4 C7 C8 8.4(4) . . . . ? O1 C7 C8 C9 15.6(4) . . . . ? C4 C7 C8 C9 -165.2(2) . . . . ? O1 C7 C8 Br1 -106.8(3) . . . . ? C4 C7 C8 Br1 72.4(3) . . . . ? C13 N1 C9 C10 1.2(4) . . . . ? C13 N1 C9 C8 -179.4(3) . . . . ? C7 C8 C9 N1 -64.4(3) . . . . ? Br1 C8 C9 N1 56.9(3) . . . . ? C7 C8 C9 C10 115.0(3) . . . . ? Br1 C8 C9 C10 -123.7(2) . . . . ? N1 C9 C10 C11 0.8(4) . . . . ? C8 C9 C10 C11 -178.6(3) . . . . ? C9 C10 C11 C12 -1.5(5) . . . . ? C10 C11 C12 C13 0.4(5) . . . . ? C9 N1 C13 C12 -2.3(5) . . . . ? C11 C12 C13 N1 1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.326 _refine_diff_density_min -1.511 _refine_diff_density_rms 0.188 # Attachment 'sl0970.cif' data_sl0970 _database_code_depnum_ccdc_archive 'CCDC 756496' #TrackingRef 'sl0970.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 Cl F N3 O' _chemical_formula_sum 'C11 H7 Cl F N3 O' _chemical_formula_weight 251.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5835(3) _cell_length_b 8.4844(4) _cell_length_c 11.9337(7) _cell_angle_alpha 105.020(3) _cell_angle_beta 93.976(3) _cell_angle_gamma 104.710(2) _cell_volume 522.56(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8738 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Very poor crystals, the data crystal was split. Initially, the cell volume appeared to be doubled. In the circumstances, this is a very good result (JED). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5552 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1841 _reflns_number_gt 1572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.5592P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1841 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_restrained_S_all 1.224 _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 Cl1 Cl 0.07356(15) 0.68585(10) 0.60196(7) 0.0417(3) Uani 1 1 d . . . F1 F 0.6981(4) 1.8811(3) 1.48024(19) 0.0594(7) Uani 1 1 d . . . N2 N 0.1132(5) 1.0454(4) 0.8833(2) 0.0365(6) Uani 1 1 d . . . O1 O 0.8362(4) 1.3316(3) 1.0437(2) 0.0478(7) Uani 1 1 d . . . N1 N 0.4097(5) 1.2571(3) 1.0155(2) 0.0363(6) Uani 1 1 d . . . H1 H 0.2796 1.2853 1.0431 0.044 Uiso 1 1 calc R . . C9 C 0.5403(6) 1.0592(4) 0.8557(3) 0.0360(7) Uani 1 1 d . . . H9 H 0.7140 1.1109 0.8821 0.043 Uiso 1 1 calc R . . N3 N 0.0314(5) 0.9114(4) 0.7870(2) 0.0380(7) Uani 1 1 d . . . C8 C 0.3584(6) 1.1175(4) 0.9158(3) 0.0313(7) Uani 1 1 d . . . C4 C 0.6429(6) 1.4941(4) 1.1826(3) 0.0344(7) Uani 1 1 d . . . C6 C 0.4629(7) 1.6237(5) 1.3467(3) 0.0499(9) Uani 1 1 d . . . H6 H 0.3271 1.6235 1.3905 0.060 Uiso 1 1 calc R . . C7 C 0.6414(6) 1.3556(4) 1.0753(3) 0.0350(7) Uani 1 1 d . . . C10 C 0.4555(6) 0.9244(4) 0.7573(3) 0.0376(8) Uani 1 1 d . . . H10 H 0.5676 0.8787 0.7115 0.045 Uiso 1 1 calc R . . C3 C 0.8630(6) 1.6260(4) 1.2222(3) 0.0389(8) Uani 1 1 d . . . H3 H 1.0008 1.6261 1.1798 0.047 Uiso 1 1 calc R . . C5 C 0.4441(7) 1.4934(5) 1.2457(3) 0.0437(8) Uani 1 1 d . . . H5 H 0.2938 1.4030 1.2196 0.052 Uiso 1 1 calc R . . C1 C 0.6810(7) 1.7527(4) 1.3820(3) 0.0418(8) Uani 1 1 d . . . C11 C 0.1965(6) 0.8567(4) 0.7271(3) 0.0343(7) Uani 1 1 d . . . C2 C 0.8835(7) 1.7571(4) 1.3227(3) 0.0421(8) Uani 1 1 d . . . H2 H 1.0334 1.8476 1.3499 0.051 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 Cl1 0.0347(5) 0.0430(5) 0.0366(5) -0.0034(4) 0.0039(3) 0.0074(4) F1 0.0569(14) 0.0534(13) 0.0506(13) -0.0124(10) 0.0047(11) 0.0143(11) N2 0.0255(14) 0.0422(15) 0.0378(15) 0.0039(12) 0.0046(11) 0.0102(12) O1 0.0280(13) 0.0531(15) 0.0514(15) -0.0006(12) 0.0085(11) 0.0080(11) N1 0.0287(14) 0.0430(15) 0.0335(14) 0.0021(12) 0.0059(11) 0.0127(12) C9 0.0243(16) 0.0416(18) 0.0396(18) 0.0072(15) 0.0056(13) 0.0091(13) N3 0.0267(14) 0.0421(16) 0.0383(15) 0.0015(12) 0.0044(12) 0.0077(12) C8 0.0260(15) 0.0345(16) 0.0331(16) 0.0093(13) 0.0037(12) 0.0083(12) C4 0.0291(16) 0.0395(18) 0.0335(17) 0.0089(14) 0.0031(13) 0.0097(14) C6 0.037(2) 0.060(2) 0.044(2) -0.0008(17) 0.0118(16) 0.0128(17) C7 0.0290(17) 0.0379(17) 0.0357(17) 0.0098(14) 0.0041(14) 0.0064(14) C10 0.0296(17) 0.0452(19) 0.0377(18) 0.0065(15) 0.0102(14) 0.0139(14) C3 0.0336(18) 0.0420(19) 0.0388(18) 0.0099(15) 0.0064(14) 0.0078(14) C5 0.0330(18) 0.0437(19) 0.045(2) 0.0025(16) 0.0073(15) 0.0036(15) C1 0.042(2) 0.0391(18) 0.0363(18) -0.0021(15) -0.0006(15) 0.0121(15) C11 0.0284(16) 0.0385(18) 0.0346(17) 0.0062(14) 0.0063(13) 0.0110(13) C2 0.0391(19) 0.0392(19) 0.0410(19) 0.0062(15) -0.0003(16) 0.0056(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 Cl1 C11 1.742(3) . ? F1 C1 1.357(4) . ? N2 C8 1.333(4) . ? N2 N3 1.345(4) . ? O1 C7 1.223(4) . ? N1 C7 1.377(4) . ? N1 C8 1.396(4) . ? N1 H1 0.8800 . ? C9 C10 1.364(5) . ? C9 C8 1.402(5) . ? C9 H9 0.9500 . ? N3 C11 1.308(4) . ? C4 C5 1.384(5) . ? C4 C3 1.390(5) . ? C4 C7 1.495(5) . ? C6 C1 1.368(5) . ? C6 C5 1.385(5) . ? C6 H6 0.9500 . ? C10 C11 1.396(5) . ? C10 H10 0.9500 . ? C3 C2 1.383(5) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C1 C2 1.372(5) . ? C2 H2 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N2 N3 119.5(3) . . ? C7 N1 C8 127.2(3) . . ? C7 N1 H1 116.4 . . ? C8 N1 H1 116.4 . . ? C10 C9 C8 116.7(3) . . ? C10 C9 H9 121.6 . . ? C8 C9 H9 121.6 . . ? C11 N3 N2 118.6(3) . . ? N2 C8 N1 111.9(3) . . ? N2 C8 C9 123.4(3) . . ? N1 C8 C9 124.7(3) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 C7 123.8(3) . . ? C3 C4 C7 116.8(3) . . ? C1 C6 C5 118.6(3) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? O1 C7 N1 122.5(3) . . ? O1 C7 C4 121.3(3) . . ? N1 C7 C4 116.2(3) . . ? C9 C10 C11 117.0(3) . . ? C9 C10 H10 121.5 . . ? C11 C10 H10 121.5 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? F1 C1 C6 118.5(3) . . ? F1 C1 C2 118.7(3) . . ? C6 C1 C2 122.8(3) . . ? N3 C11 C10 124.8(3) . . ? N3 C11 Cl1 115.4(2) . . ? C10 C11 Cl1 119.7(2) . . ? C1 C2 C3 118.1(3) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? 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 N2 N3 C11 -0.8(5) . . . . ? N3 N2 C8 N1 178.5(3) . . . . ? N3 N2 C8 C9 -1.1(5) . . . . ? C7 N1 C8 N2 176.9(3) . . . . ? C7 N1 C8 C9 -3.5(5) . . . . ? C10 C9 C8 N2 1.8(5) . . . . ? C10 C9 C8 N1 -177.7(3) . . . . ? C8 N1 C7 O1 1.9(5) . . . . ? C8 N1 C7 C4 -177.7(3) . . . . ? C5 C4 C7 O1 -156.7(3) . . . . ? C3 C4 C7 O1 20.5(5) . . . . ? C5 C4 C7 N1 22.9(5) . . . . ? C3 C4 C7 N1 -160.0(3) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C5 C4 C3 C2 -0.9(5) . . . . ? C7 C4 C3 C2 -178.2(3) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? C7 C4 C5 C6 177.8(3) . . . . ? C1 C6 C5 C4 0.3(6) . . . . ? C5 C6 C1 F1 179.3(3) . . . . ? C5 C6 C1 C2 -1.1(6) . . . . ? N2 N3 C11 C10 1.9(5) . . . . ? N2 N3 C11 Cl1 -178.6(2) . . . . ? C9 C10 C11 N3 -1.1(5) . . . . ? C9 C10 C11 Cl1 179.4(3) . . . . ? F1 C1 C2 C3 -179.5(3) . . . . ? C6 C1 C2 C3 0.8(6) . . . . ? C4 C3 C2 C1 0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.534 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.081