# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'M. Bryce' _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _publ_section_title ; Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and esters: synthesis and Suzuki-Miyaura cross-coupling reactions ; loop_ _publ_author_name 'M. Bryce' 'A. Batsanov' 'Kate M. Clapham' 'Brian Tarbit' # Attachment 'CF3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 699539' _database_code_CSD 699539 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-(trifluoromethyl)-3-pyridylboronic acid ; _chemical_name_common '6-(trifluoromethyl)-3-pyridylboronic acid' _chemical_melting_point '528 (dec.)' _chemical_formula_moiety 'C6 H5 B F3 N O2' _chemical_formula_sum 'C6 H5 B F3 N O2' _chemical_formula_weight 190.92 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.7372(9) _cell_length_b 7.0418(9) _cell_length_c 13.8744(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.18(1) _cell_angle_gamma 90.00 _cell_volume 752.84(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3724 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7241 _exptl_absorpt_correction_T_max 0.8621 _exptl_absorpt_process_details 'SADABS-2006/1 (Bruker)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.0650 -1.00 0.00 0.00 0.0650 0.00 1.00 -2.00 0.1200 0.00 -1.00 -2.00 0.1200 -3.00 -2.00 4.00 0.1200 -2.00 2.00 3.00 0.1200 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 3 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. Unsystematic twinning. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 6652 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 28.99 _reflns_number_total 2001 _reflns_number_gt 1658 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. The CF~3~ group is rotationally disordered. The major positions of F(1), F(2), F(3) were refined anisotropically with occupancies 0.85, minor positions (labelled B) refined isotropically with occupancies 0.15. ; _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^)+(0.0423P)^2^+0.3583P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2001 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 O1 O 0.53484(12) 0.84963(14) 0.09685(7) 0.0221(2) Uani 1 1 d . . . H01 H 0.583(3) 0.813(3) 0.1495(16) 0.044(5) Uiso 1 1 d . . . O2 O 0.32935(14) 0.80981(15) -0.03702(7) 0.0281(2) Uani 1 1 d . . . H02 H 0.372(3) 0.909(3) -0.0548(15) 0.044(6) Uiso 1 1 d . . . F1 F 0.0195(2) -0.0461(2) 0.13779(9) 0.0511(4) Uani 0.85 1 d P A 1 F2 F 0.24432(16) -0.0660(2) 0.23911(14) 0.0467(4) Uani 0.85 1 d P A 1 F3 F 0.0277(2) 0.09739(17) 0.27347(11) 0.0449(4) Uani 0.85 1 d P A 1 F1B F 0.0991(8) -0.0762(10) 0.1342(5) 0.0256(16) Uiso 0.15 1 d P A 2 F2B F 0.2209(9) -0.0162(10) 0.2695(5) 0.0222(15) Uiso 0.15 1 d P A 2 F3B F -0.0244(8) 0.0967(10) 0.2300(5) 0.0280(15) Uiso 0.15 1 d P A 2 N1 N 0.31003(13) 0.32592(15) 0.21617(7) 0.0178(2) Uani 1 1 d . . . C1 C 0.12231(16) 0.05326(18) 0.20099(9) 0.0202(3) Uani 1 1 d . . . C2 C 0.19802(16) 0.22670(17) 0.15665(9) 0.0178(3) Uani 1 1 d . A . C3 C 0.14768(18) 0.2778(2) 0.06200(10) 0.0233(3) Uani 1 1 d . . . H3 H 0.066(2) 0.206(3) 0.0212(13) 0.030(4) Uiso 1 1 d . . . C4 C 0.21725(17) 0.44390(19) 0.02730(9) 0.0215(3) Uani 1 1 d . A . H4 H 0.183(2) 0.481(3) -0.0355(12) 0.027(4) Uiso 1 1 d . . . C5 C 0.33168(16) 0.55432(17) 0.08698(9) 0.0180(2) Uani 1 1 d . . . C6 C 0.37272(16) 0.48692(18) 0.18098(9) 0.0186(3) Uani 1 1 d . A . H6 H 0.450(2) 0.556(2) 0.2268(12) 0.024(4) Uiso 1 1 d . . . B B 0.40473(19) 0.7469(2) 0.04865(10) 0.0195(3) Uani 1 1 d . A . 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 O1 0.0279(5) 0.0206(5) 0.0171(4) 0.0041(3) -0.0029(4) -0.0043(4) O2 0.0347(5) 0.0244(5) 0.0233(5) 0.0083(4) -0.0078(4) -0.0089(4) F1 0.0762(11) 0.0400(8) 0.0330(6) 0.0075(5) -0.0179(7) -0.0398(8) F2 0.0279(6) 0.0270(7) 0.0858(12) 0.0281(7) 0.0078(7) 0.0053(5) F3 0.0616(9) 0.0266(6) 0.0527(9) -0.0045(6) 0.0396(8) -0.0091(6) N1 0.0193(5) 0.0168(5) 0.0172(5) 0.0001(4) 0.0002(4) 0.0001(4) C1 0.0215(6) 0.0170(6) 0.0220(6) -0.0016(5) 0.0008(5) -0.0021(5) C2 0.0187(5) 0.0152(6) 0.0194(6) -0.0009(4) 0.0017(4) 0.0005(4) C3 0.0268(6) 0.0220(6) 0.0201(6) -0.0023(5) -0.0033(5) -0.0039(5) C4 0.0257(6) 0.0217(6) 0.0166(6) 0.0007(5) -0.0015(5) 0.0000(5) C5 0.0191(5) 0.0165(6) 0.0183(6) 0.0007(4) 0.0016(4) 0.0016(4) C6 0.0190(5) 0.0177(6) 0.0187(6) -0.0008(5) -0.0007(4) -0.0007(5) B 0.0229(7) 0.0183(6) 0.0174(6) 0.0007(5) 0.0015(5) 0.0004(5) _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 O1 B 1.3646(17) . ? O1 H01 0.83(2) . ? O2 B 1.3504(16) . ? O2 H02 0.82(2) . ? F1 C1 1.3286(16) . ? F2 C1 1.3363(17) . ? F3 C1 1.3331(17) . ? F1B C1 1.300(7) . ? F2B C1 1.263(7) . ? F3B C1 1.276(7) . ? N1 C2 1.3387(15) . ? N1 C6 1.3423(16) . ? C1 C2 1.5094(18) . ? C2 C3 1.3833(17) . ? C3 C4 1.3912(19) . ? C3 H3 0.954(17) . ? C4 C5 1.3935(17) . ? C4 H4 0.926(17) . ? C5 C6 1.3973(17) . ? C5 B 1.5799(19) . ? C6 H6 0.961(17) . ? 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 B O1 H01 121.4(15) . . ? B O2 H02 113.2(14) . . ? C2 N1 C6 116.84(10) . . ? F2B C1 F3B 110.5(4) . . ? F2B C1 F1B 107.5(4) . . ? F3B C1 F1B 108.9(4) . . ? F1 C1 F3 106.47(14) . . ? F1 C1 F2 106.86(14) . . ? F3 C1 F2 105.33(14) . . ? F2B C1 C2 113.0(3) . . ? F3B C1 C2 108.9(3) . . ? F1B C1 C2 108.1(3) . . ? F1 C1 C2 112.85(11) . . ? F3 C1 C2 112.25(11) . . ? F2 C1 C2 112.54(11) . . ? N1 C2 C3 124.12(12) . . ? N1 C2 C1 115.11(11) . . ? C3 C2 C1 120.74(11) . . ? C2 C3 C4 117.57(12) . . ? C2 C3 H3 122.6(11) . . ? C4 C3 H3 119.9(11) . . ? C3 C4 C5 120.55(12) . . ? C3 C4 H4 118.5(11) . . ? C5 C4 H4 120.9(11) . . ? C4 C5 C6 116.34(11) . . ? C4 C5 B 120.43(11) . . ? C6 C5 B 123.21(11) . . ? N1 C6 C5 124.56(11) . . ? N1 C6 H6 114.0(10) . . ? C5 C6 H6 121.4(10) . . ? O2 B O1 119.90(12) . . ? O2 B C5 116.01(11) . . ? O1 B C5 124.09(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H01 N1 0.83(2) 1.97(2) 2.7633(14) 159(2) 2_655 O2 H02 O1 0.82(2) 1.96(2) 2.7753(14) 178(2) 3_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.356 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.048 #===================================END data_30b _database_code_depnum_ccdc_archive 'CCDC 699540' _database_code_CSD 699540 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(Trifluoromethyl)-1-(4-methoxyphenyl)-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole ; _chemical_name_common ; 3-(Trifluoromethyl)-1-(4-methoxyphenyl)-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole ; _chemical_melting_point 371.9(10) _chemical_formula_moiety 'C17 H20 B F3 N2 O3' _chemical_formula_sum 'C17 H20 B F3 N2 O3' _chemical_formula_weight 368.16 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.1172(13) _cell_length_b 16.9563(18) _cell_length_c 9.5326(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.12(2) _cell_angle_gamma 90.00 _cell_volume 1801.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9896 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 29.97 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 5s exposure), every run at a different \f angle. Crystal to detector distance 4.40 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 21847 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5125 _reflns_number_gt 4106 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT version 7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0562P)^2^+0.6725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5125 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 B B 0.27517(11) 0.25178(7) 0.61351(14) 0.0198(2) Uani 1 1 d . . . F1 F 0.26386(8) -0.10498(5) 0.57769(14) 0.0523(3) Uani 1 1 d . . . F2 F 0.13605(11) -0.06317(6) 0.66397(13) 0.0559(3) Uani 1 1 d . . . F3 F 0.09985(9) -0.05217(6) 0.42836(11) 0.0492(3) Uani 1 1 d . . . O1 O 0.35922(7) 0.30032(5) 0.59823(9) 0.02224(17) Uani 1 1 d . . . O2 O 0.17633(7) 0.28909(5) 0.61667(9) 0.02225(17) Uani 1 1 d . . . O3 O 0.86655(8) 0.19412(6) 0.99037(11) 0.0301(2) Uani 1 1 d . . . N11 N 0.38654(8) 0.11577(5) 0.67129(11) 0.01980(19) Uani 1 1 d . . . N12 N 0.36528(9) 0.03744(6) 0.65628(11) 0.0218(2) Uani 1 1 d . . . C1 C 0.18805(11) -0.04683(7) 0.56740(15) 0.0270(2) Uani 1 1 d . . . C2 C 0.90567(11) 0.23329(8) 1.13452(15) 0.0289(3) Uani 1 1 d . . . H2A H 0.8721(15) 0.2873(11) 1.1264(19) 0.035(4) Uiso 1 1 d . . . H2B H 0.8807(15) 0.2037(11) 1.206(2) 0.038(5) Uiso 1 1 d . . . H2C H 0.9934(16) 0.2371(10) 1.1702(19) 0.036(4) Uiso 1 1 d . . . C3 C 0.18616(10) 0.37180(6) 0.57560(12) 0.0208(2) Uani 1 1 d . . . C4 C 0.32428(10) 0.38073(7) 0.62419(12) 0.0212(2) Uani 1 1 d . . . C5 C 0.13198(13) 0.42463(8) 0.66031(15) 0.0289(3) Uani 1 1 d . . . H52 H 0.1701(15) 0.4160(10) 0.774(2) 0.037(4) Uiso 1 1 d . . . H53 H 0.0460(16) 0.4151(10) 0.6261(19) 0.035(4) Uiso 1 1 d . . . H51 H 0.1442(16) 0.4822(12) 0.640(2) 0.045(5) Uiso 1 1 d . . . C6 C 0.11498(12) 0.37812(8) 0.40423(14) 0.0279(2) Uani 1 1 d . . . H61 H 0.1505(14) 0.3438(10) 0.3481(18) 0.031(4) Uiso 1 1 d . . . H62 H 0.0310(15) 0.3623(10) 0.3801(19) 0.035(4) Uiso 1 1 d . . . H63 H 0.1154(16) 0.4320(11) 0.370(2) 0.040(5) Uiso 1 1 d . . . C7 C 0.36148(12) 0.43907(8) 0.53019(15) 0.0272(2) Uani 1 1 d . . . H72 H 0.3282(14) 0.4250(10) 0.4211(19) 0.032(4) Uiso 1 1 d . . . H71 H 0.3342(14) 0.4929(10) 0.5421(18) 0.034(4) Uiso 1 1 d . . . H73 H 0.4511(16) 0.4408(10) 0.5677(19) 0.035(4) Uiso 1 1 d . . . C8 C 0.39116(12) 0.39630(8) 0.79436(14) 0.0291(3) Uani 1 1 d . . . H81 H 0.3655(14) 0.3577(10) 0.8572(18) 0.032(4) Uiso 1 1 d . . . H82 H 0.4758(16) 0.3909(11) 0.817(2) 0.039(4) Uiso 1 1 d . . . H83 H 0.3753(16) 0.4505(11) 0.819(2) 0.042(5) Uiso 1 1 d . . . C13 C 0.24572(10) 0.03227(7) 0.59543(13) 0.0215(2) Uani 1 1 d . . . C14 C 0.19009(10) 0.10609(7) 0.57234(13) 0.0216(2) Uani 1 1 d . . . H14 H 0.1042(14) 0.1177(9) 0.5286(17) 0.027(4) Uiso 1 1 d . . . C15 C 0.28351(10) 0.16012(7) 0.62207(12) 0.0198(2) Uani 1 1 d . . . C21 C 0.50832(10) 0.14131(6) 0.75049(12) 0.0199(2) Uani 1 1 d . . . C22 C 0.53939(10) 0.18443(7) 0.88413(13) 0.0234(2) Uani 1 1 d . . . H22 H 0.4798(15) 0.1987(10) 0.9221(18) 0.032(4) Uiso 1 1 d . . . C23 C 0.65897(11) 0.20428(7) 0.96758(14) 0.0244(2) Uani 1 1 d . . . H23 H 0.6805(15) 0.2331(10) 1.0634(19) 0.035(4) Uiso 1 1 d . . . C24 C 0.74661(10) 0.18001(7) 0.91643(13) 0.0230(2) Uani 1 1 d . . . C25 C 0.71417(10) 0.13713(7) 0.78074(13) 0.0226(2) Uani 1 1 d . . . H25 H 0.7780(14) 0.1208(9) 0.7475(17) 0.026(4) Uiso 1 1 d . . . C26 C 0.59494(10) 0.11812(7) 0.69722(13) 0.0211(2) Uani 1 1 d . . . H26 H 0.5725(13) 0.0881(9) 0.6033(17) 0.023(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B 0.0187(5) 0.0199(6) 0.0202(5) -0.0012(4) 0.0068(4) -0.0016(4) F1 0.0340(5) 0.0214(4) 0.0922(8) -0.0132(4) 0.0147(5) -0.0008(3) F2 0.0857(8) 0.0373(5) 0.0664(7) -0.0115(4) 0.0531(6) -0.0287(5) F3 0.0455(5) 0.0363(5) 0.0453(5) -0.0044(4) -0.0041(4) -0.0164(4) O1 0.0202(4) 0.0196(4) 0.0277(4) 0.0006(3) 0.0103(3) -0.0005(3) O2 0.0210(4) 0.0185(4) 0.0290(4) 0.0001(3) 0.0118(3) -0.0007(3) O3 0.0172(4) 0.0361(5) 0.0350(5) -0.0091(4) 0.0081(3) -0.0026(3) N11 0.0183(4) 0.0179(4) 0.0233(4) -0.0006(3) 0.0083(3) -0.0008(3) N12 0.0233(5) 0.0182(4) 0.0242(4) -0.0017(3) 0.0096(4) -0.0013(3) C1 0.0256(6) 0.0218(5) 0.0330(6) -0.0043(4) 0.0109(5) -0.0034(4) C2 0.0204(6) 0.0279(6) 0.0338(6) -0.0058(5) 0.0057(5) -0.0018(5) C3 0.0227(5) 0.0177(5) 0.0224(5) 0.0005(4) 0.0094(4) 0.0004(4) C4 0.0235(5) 0.0184(5) 0.0215(5) -0.0001(4) 0.0087(4) -0.0021(4) C5 0.0349(7) 0.0235(6) 0.0327(6) -0.0011(5) 0.0179(5) 0.0033(5) C6 0.0249(6) 0.0318(6) 0.0233(5) 0.0011(5) 0.0054(4) 0.0015(5) C7 0.0315(6) 0.0232(6) 0.0293(6) 0.0022(4) 0.0145(5) -0.0043(5) C8 0.0315(7) 0.0280(6) 0.0228(5) -0.0013(5) 0.0053(5) -0.0074(5) C13 0.0222(5) 0.0204(5) 0.0226(5) -0.0031(4) 0.0096(4) -0.0032(4) C14 0.0194(5) 0.0226(5) 0.0226(5) -0.0017(4) 0.0081(4) -0.0017(4) C15 0.0185(5) 0.0205(5) 0.0211(5) -0.0007(4) 0.0086(4) -0.0006(4) C21 0.0174(5) 0.0181(5) 0.0231(5) 0.0011(4) 0.0068(4) -0.0005(4) C22 0.0196(5) 0.0245(5) 0.0270(5) -0.0027(4) 0.0100(4) -0.0001(4) C23 0.0209(5) 0.0247(6) 0.0273(5) -0.0047(4) 0.0091(4) -0.0009(4) C24 0.0176(5) 0.0218(5) 0.0283(5) 0.0006(4) 0.0076(4) -0.0004(4) C25 0.0204(5) 0.0230(5) 0.0266(5) 0.0017(4) 0.0115(4) 0.0017(4) C26 0.0217(5) 0.0200(5) 0.0226(5) 0.0010(4) 0.0097(4) 0.0009(4) _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 B O1 1.3610(14) . ? B O2 1.3652(15) . ? B C15 1.5575(17) . ? F1 C1 1.3247(15) . ? F2 C1 1.3330(16) . ? F3 C1 1.3396(16) . ? O1 C4 1.4771(14) . ? O2 C3 1.4734(13) . ? O3 C24 1.3645(14) . ? O3 C2 1.4291(16) . ? N11 N12 1.3497(13) . ? N11 C15 1.3727(14) . ? N11 C21 1.4353(14) . ? N12 C13 1.3353(15) . ? C1 C13 1.4873(16) . ? C2 H2A 0.992(18) . ? C2 H2B 0.982(18) . ? C2 H2C 0.982(17) . ? C3 C5 1.5172(16) . ? C3 C6 1.5224(16) . ? C3 C4 1.5587(16) . ? C4 C7 1.5172(16) . ? C4 C8 1.5250(16) . ? C5 H52 1.005(17) . ? C5 H53 0.975(17) . ? C5 H51 1.02(2) . ? C6 H61 0.995(16) . ? C6 H62 0.988(17) . ? C6 H63 0.969(19) . ? C7 H72 0.986(17) . ? C7 H71 0.993(17) . ? C7 H73 1.001(17) . ? C8 H81 1.016(17) . ? C8 H82 0.966(18) . ? C8 H83 0.986(19) . ? C13 C14 1.3975(16) . ? C14 C15 1.3871(15) . ? C14 H14 0.977(15) . ? C21 C22 1.3865(16) . ? C21 C26 1.3903(15) . ? C22 C23 1.3930(17) . ? C22 H22 0.958(17) . ? C23 C24 1.3934(16) . ? C23 H23 0.976(17) . ? C24 C25 1.3989(17) . ? C25 C26 1.3862(16) . ? C25 H25 0.984(15) . ? C26 H26 0.972(15) . ? 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 O1 B O2 114.96(10) . . ? O1 B C15 124.97(10) . . ? O2 B C15 120.05(10) . . ? B O1 C4 105.34(9) . . ? B O2 C3 105.79(8) . . ? C24 O3 C2 117.52(10) . . ? N12 N11 C15 113.12(9) . . ? N12 N11 C21 117.82(9) . . ? C15 N11 C21 128.58(9) . . ? C13 N12 N11 103.89(9) . . ? F1 C1 F2 107.23(12) . . ? F1 C1 F3 106.47(11) . . ? F2 C1 F3 105.03(11) . . ? F1 C1 C13 113.25(10) . . ? F2 C1 C13 112.30(10) . . ? F3 C1 C13 112.01(10) . . ? O3 C2 H2A 112.5(10) . . ? O3 C2 H2B 110.5(10) . . ? H2A C2 H2B 107.3(14) . . ? O3 C2 H2C 105.6(10) . . ? H2A C2 H2C 108.7(14) . . ? H2B C2 H2C 112.2(14) . . ? O2 C3 C5 108.88(9) . . ? O2 C3 C6 106.33(9) . . ? C5 C3 C6 110.39(10) . . ? O2 C3 C4 101.71(8) . . ? C5 C3 C4 115.03(10) . . ? C6 C3 C4 113.69(10) . . ? O1 C4 C7 109.37(9) . . ? O1 C4 C8 105.69(9) . . ? C7 C4 C8 110.99(10) . . ? O1 C4 C3 101.86(8) . . ? C7 C4 C3 114.91(10) . . ? C8 C4 C3 113.14(10) . . ? C3 C5 H52 112.0(10) . . ? C3 C5 H53 110.7(10) . . ? H52 C5 H53 108.4(14) . . ? C3 C5 H51 109.9(10) . . ? H52 C5 H51 107.7(14) . . ? H53 C5 H51 108.1(14) . . ? C3 C6 H61 110.7(9) . . ? C3 C6 H62 109.1(10) . . ? H61 C6 H62 109.8(14) . . ? C3 C6 H63 110.4(11) . . ? H61 C6 H63 108.2(14) . . ? H62 C6 H63 108.6(14) . . ? C4 C7 H72 111.8(9) . . ? C4 C7 H71 110.0(10) . . ? H72 C7 H71 109.1(13) . . ? C4 C7 H73 109.9(10) . . ? H72 C7 H73 108.7(13) . . ? H71 C7 H73 107.2(14) . . ? C4 C8 H81 111.0(9) . . ? C4 C8 H82 107.4(10) . . ? H81 C8 H82 110.4(14) . . ? C4 C8 H83 110.1(10) . . ? H81 C8 H83 109.0(14) . . ? H82 C8 H83 108.9(15) . . ? N12 C13 C14 112.56(10) . . ? N12 C13 C1 119.36(10) . . ? C14 C13 C1 128.02(10) . . ? C15 C14 C13 105.03(10) . . ? C15 C14 H14 127.0(9) . . ? C13 C14 H14 127.9(9) . . ? N11 C15 C14 105.40(10) . . ? N11 C15 B 126.60(10) . . ? C14 C15 B 127.85(10) . . ? C22 C21 C26 120.87(10) . . ? C22 C21 N11 119.64(10) . . ? C26 C21 N11 119.35(10) . . ? C21 C22 C23 119.89(11) . . ? C21 C22 H22 120.5(10) . . ? C23 C22 H22 119.5(10) . . ? C22 C23 C24 119.58(11) . . ? C22 C23 H23 119.4(10) . . ? C24 C23 H23 121.0(10) . . ? O3 C24 C23 124.82(11) . . ? O3 C24 C25 115.11(10) . . ? C23 C24 C25 120.07(11) . . ? C26 C25 C24 120.20(10) . . ? C26 C25 H25 121.6(9) . . ? C24 C25 H25 118.2(9) . . ? C25 C26 C21 119.37(11) . . ? C25 C26 H26 120.2(9) . . ? C21 C26 H26 120.4(9) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.349 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.053 #===================================END data_36 _database_code_depnum_ccdc_archive 'CCDC 699541' _database_code_CSD 699541 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-{3-(trifluoromethyl)-1-phenyl-1H-pyrazol-5-yl}- 3-nitropyridin-2-amine ; _chemical_name_common ;5-(3-(trifluoromethyl)-1-phenyl-1H-pyrazol-5-yl)-3- nitropyridin-2-amine ; _chemical_melting_point 440.5(8) _chemical_formula_moiety 'C15 H10 F3 N5 O2' _chemical_formula_sum 'C15 H10 F3 N5 O2' _chemical_formula_weight 349.28 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' _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 5.8768(8) _cell_length_b 8.4512(12) _cell_length_c 15.156(2) _cell_angle_alpha 83.57(2) _cell_angle_beta 82.56(3) _cell_angle_gamma 85.02(3) _cell_volume 739.74(18) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 29.06 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 8679 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 29.06 _reflns_number_total 3896 _reflns_number_gt 3259 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT version 7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^+0.2192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3896 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 -0.09484(14) 0.95666(9) 0.10237(5) 0.03292(19) Uani 1 1 d . . . F2 F -0.10735(14) 1.03884(8) 0.23279(5) 0.03150(18) Uani 1 1 d . . . F3 F -0.34655(13) 0.87341(10) 0.20904(6) 0.0375(2) Uani 1 1 d . . . O1 O 0.81624(17) 0.01945(10) 0.43393(6) 0.0307(2) Uani 1 1 d . . . O2 O 0.48195(17) 0.02974(10) 0.38671(7) 0.0301(2) Uani 1 1 d . . . N1 N 0.76139(17) 0.51583(11) 0.42716(6) 0.0203(2) Uani 1 1 d . . . N2 N 0.96210(19) 0.28744(13) 0.47916(7) 0.0248(2) Uani 1 1 d . . . H1N H 1.041(3) 0.349(2) 0.5049(11) 0.032(4) Uiso 1 1 d . . . H2N H 0.994(3) 0.185(2) 0.4815(12) 0.044(5) Uiso 1 1 d . . . N3 N 0.64548(18) 0.09495(11) 0.40560(6) 0.0225(2) Uani 1 1 d . . . N11 N 0.23975(16) 0.55736(11) 0.20156(6) 0.01908(19) Uani 1 1 d . . . N12 N 0.08208(16) 0.65943(11) 0.16259(7) 0.0210(2) Uani 1 1 d . . . C1 C -0.1272(2) 0.91057(14) 0.19031(8) 0.0226(2) Uani 1 1 d . . . C2 C 0.79155(19) 0.35311(13) 0.43381(7) 0.0192(2) Uani 1 1 d . . . C3 C 0.6393(2) 0.26815(12) 0.39406(7) 0.0186(2) Uani 1 1 d . . . C4 C 0.4750(2) 0.34884(13) 0.34425(7) 0.0190(2) Uani 1 1 d . . . H4 H 0.380(2) 0.2857(17) 0.3189(10) 0.023(3) Uiso 1 1 d . . . C5 C 0.45844(19) 0.51502(12) 0.33322(7) 0.0182(2) Uani 1 1 d . . . C6 C 0.6037(2) 0.59114(13) 0.37892(7) 0.0198(2) Uani 1 1 d . . . H6 H 0.593(2) 0.7079(18) 0.3756(10) 0.023(3) Uiso 1 1 d . . . C13 C 0.04060(19) 0.77549(13) 0.21597(7) 0.0190(2) Uani 1 1 d . . . C14 C 0.1676(2) 0.75161(13) 0.28929(8) 0.0202(2) Uani 1 1 d . . . H14 H 0.166(3) 0.8185(19) 0.3373(11) 0.029(4) Uiso 1 1 d . . . C15 C 0.29562(19) 0.60789(12) 0.27806(7) 0.0180(2) Uani 1 1 d . . . C21 C 0.3543(2) 0.43500(13) 0.14911(7) 0.0197(2) Uani 1 1 d . . . C22 C 0.5828(2) 0.44669(14) 0.11351(8) 0.0227(2) Uani 1 1 d . . . H22 H 0.666(3) 0.5329(18) 0.1289(10) 0.026(4) Uiso 1 1 d . . . C23 C 0.6820(2) 0.33893(15) 0.05418(8) 0.0271(3) Uani 1 1 d . . . H23 H 0.838(3) 0.351(2) 0.0261(11) 0.034(4) Uiso 1 1 d . . . C24 C 0.5539(2) 0.22243(15) 0.03158(9) 0.0297(3) Uani 1 1 d . . . H24 H 0.623(3) 0.157(2) -0.0116(11) 0.033(4) Uiso 1 1 d . . . C25 C 0.3282(3) 0.21010(15) 0.06927(10) 0.0316(3) Uani 1 1 d . . . H25 H 0.236(3) 0.133(2) 0.0530(12) 0.042(5) Uiso 1 1 d . . . C26 C 0.2261(2) 0.31674(14) 0.12886(9) 0.0262(2) Uani 1 1 d . . . H26 H 0.073(3) 0.3127(19) 0.1534(10) 0.029(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0400(5) 0.0306(4) 0.0247(4) 0.0046(3) -0.0064(3) 0.0110(3) F2 0.0385(4) 0.0201(3) 0.0348(4) -0.0042(3) -0.0054(3) 0.0070(3) F3 0.0197(4) 0.0337(4) 0.0559(5) 0.0062(4) -0.0048(3) 0.0032(3) O1 0.0422(5) 0.0185(4) 0.0323(5) -0.0002(3) -0.0161(4) 0.0074(4) O2 0.0356(5) 0.0186(4) 0.0379(5) -0.0021(3) -0.0087(4) -0.0060(3) N1 0.0239(5) 0.0165(4) 0.0215(5) -0.0003(3) -0.0077(4) -0.0013(3) N2 0.0291(6) 0.0187(5) 0.0286(5) -0.0010(4) -0.0141(4) 0.0019(4) N3 0.0315(5) 0.0156(4) 0.0202(5) -0.0008(3) -0.0048(4) 0.0005(4) N11 0.0187(5) 0.0173(4) 0.0221(5) -0.0021(3) -0.0078(4) 0.0019(3) N12 0.0189(5) 0.0200(4) 0.0241(5) -0.0010(4) -0.0076(4) 0.0036(3) C1 0.0220(6) 0.0203(5) 0.0238(6) 0.0009(4) -0.0025(4) 0.0025(4) C2 0.0226(6) 0.0176(5) 0.0172(5) 0.0000(4) -0.0040(4) 0.0001(4) C3 0.0241(5) 0.0135(4) 0.0181(5) -0.0007(4) -0.0038(4) 0.0002(4) C4 0.0217(5) 0.0168(5) 0.0191(5) -0.0014(4) -0.0046(4) -0.0019(4) C5 0.0198(5) 0.0162(5) 0.0184(5) -0.0004(4) -0.0043(4) 0.0001(4) C6 0.0227(6) 0.0158(5) 0.0212(5) -0.0002(4) -0.0060(4) -0.0010(4) C13 0.0177(5) 0.0171(5) 0.0213(5) 0.0005(4) -0.0025(4) 0.0004(4) C14 0.0218(5) 0.0177(5) 0.0211(5) -0.0011(4) -0.0042(4) 0.0003(4) C15 0.0189(5) 0.0163(5) 0.0191(5) 0.0000(4) -0.0048(4) -0.0020(4) C21 0.0227(5) 0.0166(5) 0.0202(5) -0.0019(4) -0.0079(4) 0.0031(4) C22 0.0222(6) 0.0233(5) 0.0235(5) -0.0014(4) -0.0091(4) 0.0012(4) C23 0.0242(6) 0.0308(6) 0.0252(6) -0.0014(5) -0.0070(5) 0.0086(5) C24 0.0387(7) 0.0222(5) 0.0282(6) -0.0067(5) -0.0099(5) 0.0116(5) C25 0.0402(7) 0.0202(5) 0.0372(7) -0.0081(5) -0.0112(6) -0.0014(5) C26 0.0255(6) 0.0220(5) 0.0323(6) -0.0046(5) -0.0072(5) -0.0010(4) _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 C1 1.3400(14) . ? F2 C1 1.3420(14) . ? F3 C1 1.3406(14) . ? O1 N3 1.2400(13) . ? O2 N3 1.2279(14) . ? N1 C6 1.3293(14) . ? N1 C2 1.3653(14) . ? N2 C2 1.3347(15) . ? N2 H1N 0.878(17) . ? N2 H2N 0.872(19) . ? N3 C3 1.4524(14) . ? N11 N12 1.3566(13) . ? N11 C15 1.3669(14) . ? N11 C21 1.4420(15) . ? N12 C13 1.3270(15) . ? C1 C13 1.4936(16) . ? C2 C3 1.4239(16) . ? C3 C4 1.3877(15) . ? C4 C5 1.3920(14) . ? C4 H4 0.948(15) . ? C5 C6 1.4038(16) . ? C5 C15 1.4698(15) . ? C6 H6 0.979(15) . ? C13 C14 1.4038(16) . ? C14 C15 1.3875(15) . ? C14 H14 0.969(16) . ? C21 C26 1.3858(17) . ? C21 C22 1.3881(17) . ? C22 C23 1.3906(18) . ? C22 H22 0.975(15) . ? C23 C24 1.3873(19) . ? C23 H23 0.968(17) . ? C24 C25 1.383(2) . ? C24 H24 0.931(17) . ? C25 C26 1.3915(19) . ? C25 H25 0.950(18) . ? C26 H26 0.931(16) . ? 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 119.80(10) . . ? C2 N2 H1N 119.2(11) . . ? C2 N2 H2N 118.9(12) . . ? H1N N2 H2N 121.8(16) . . ? O2 N3 O1 122.91(10) . . ? O2 N3 C3 118.64(10) . . ? O1 N3 C3 118.46(10) . . ? N12 N11 C15 112.54(9) . . ? N12 N11 C21 116.65(9) . . ? C15 N11 C21 129.43(9) . . ? C13 N12 N11 103.89(9) . . ? F1 C1 F3 106.35(10) . . ? F1 C1 F2 107.15(9) . . ? F3 C1 F2 106.92(10) . . ? F1 C1 C13 111.52(10) . . ? F3 C1 C13 112.93(10) . . ? F2 C1 C13 111.62(10) . . ? N2 C2 N1 116.00(10) . . ? N2 C2 C3 125.65(10) . . ? N1 C2 C3 118.34(10) . . ? C4 C3 C2 120.86(10) . . ? C4 C3 N3 117.45(10) . . ? C2 C3 N3 121.67(10) . . ? C3 C4 C5 119.58(10) . . ? C3 C4 H4 117.0(9) . . ? C5 C4 H4 123.4(9) . . ? C4 C5 C6 116.53(10) . . ? C4 C5 C15 122.43(10) . . ? C6 C5 C15 121.04(9) . . ? N1 C6 C5 124.61(10) . . ? N1 C6 H6 115.7(8) . . ? C5 C6 H6 119.7(8) . . ? N12 C13 C14 113.19(10) . . ? N12 C13 C1 117.24(10) . . ? C14 C13 C1 129.56(11) . . ? C15 C14 C13 103.97(10) . . ? C15 C14 H14 127.4(9) . . ? C13 C14 H14 128.6(9) . . ? N11 C15 C14 106.41(10) . . ? N11 C15 C5 122.47(10) . . ? C14 C15 C5 131.11(10) . . ? C26 C21 C22 121.73(11) . . ? C26 C21 N11 118.53(11) . . ? C22 C21 N11 119.47(10) . . ? C21 C22 C23 118.64(11) . . ? C21 C22 H22 118.9(9) . . ? C23 C22 H22 122.4(9) . . ? C24 C23 C22 120.22(12) . . ? C24 C23 H23 120.6(10) . . ? C22 C23 H23 119.1(10) . . ? C25 C24 C23 120.39(12) . . ? C25 C24 H24 121.8(10) . . ? C23 C24 H24 117.7(10) . . ? C24 C25 C26 120.18(12) . . ? C24 C25 H25 121.5(11) . . ? C26 C25 H25 118.3(11) . . ? C21 C26 C25 118.80(12) . . ? C21 C26 H26 119.6(10) . . ? C25 C26 H26 121.5(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H1N N1 0.878(17) 2.126(18) 3.0025(16) 176.1(15) 2_766 N2 H2N O1 0.872(19) 2.057(19) 2.6778(15) 127.4(15) . N2 H2N O1 0.872(19) 2.323(19) 3.0416(15) 139.8(16) 2_756 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.330 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.044 #===================================END data_51 _database_code_depnum_ccdc_archive 'CCDC 699542' _database_code_CSD 699542 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-{3-(trifluoromethyl)-4-(6-methoxypyridin-3-yl)-1-phenyl-1H- pyrazol-5-yl)pyridine ; _chemical_name_common ; 2-(3-(trifluoromethyl)-4-(6-methoxypyridin-3-yl)-1-phenyl-1H- pyrazol-5-yl)pyridine ; _chemical_melting_point 402.1(12) _chemical_formula_moiety 'C21 H15 F3 N4 O' _chemical_formula_sum 'C21 H15 F3 N4 O' _chemical_formula_weight 396.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.3449(4) _cell_length_b 17.3757(6) _cell_length_c 12.7303(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.65(1) _cell_angle_gamma 90.00 _cell_volume 1839.80(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 1.00 0.1300 0.00 1.00 -1.00 0.1300 0.00 1.00 1.00 0.1500 0.00 -1.00 -1.00 0.1500 1.00 0.00 0.00 0.1750 -1.00 0.00 0.00 0.1750 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 3 runs of narrow-frame \w-scans (scan width 0.3\% \w, 20s exposure), every run at a different \f angle. Crystal to detector distance 4.85 cm. ; _diffrn_ambient_temperature 120(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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 20934 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4221 _reflns_number_gt 3724 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 7.46A (Bruker, 2007)' _computing_data_reduction 'SAINT version 7.46A (Bruker, 2007)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0502P)^2^+0.5414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4221 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.96707(9) 0.33389(5) 0.33484(7) 0.0397(2) Uani 1 1 d . . . F2 F 0.92617(9) 0.23518(5) 0.42877(7) 0.0400(2) Uani 1 1 d . . . F3 F 0.83708(10) 0.23818(6) 0.26614(7) 0.0520(3) Uani 1 1 d . . . O O 0.79054(12) 0.52081(5) -0.02831(7) 0.0336(2) Uani 1 1 d . . . N1 N 0.51597(11) 0.33871(5) 0.48025(7) 0.01951(19) Uani 1 1 d . . . N2 N 0.64842(11) 0.29461(5) 0.47475(7) 0.0215(2) Uani 1 1 d . . . N3 N 0.30649(11) 0.47372(5) 0.47176(7) 0.0211(2) Uani 1 1 d . . . N4 N 0.73988(13) 0.52558(6) 0.14727(8) 0.0262(2) Uani 1 1 d . . . C1 C 0.8478(2) 0.59814(8) -0.01505(12) 0.0425(4) Uani 1 1 d . . . H1A H 0.757(2) 0.6314(10) -0.0016(12) 0.039(4) Uiso 1 1 d . . . H1B H 0.889(2) 0.6116(10) -0.0831(13) 0.045(4) Uiso 1 1 d . . . H1C H 0.934(2) 0.6034(11) 0.0421(16) 0.060(5) Uiso 1 1 d . . . C2 C 0.85736(13) 0.28048(7) 0.35370(9) 0.0249(2) Uani 1 1 d . . . C3 C 0.70482(13) 0.31550(6) 0.38412(8) 0.0205(2) Uani 1 1 d . . . C4 C 0.61125(12) 0.37256(6) 0.33010(8) 0.0192(2) Uani 1 1 d . . . C5 C 0.48909(12) 0.38664(6) 0.39534(8) 0.0191(2) Uani 1 1 d . . . C6 C 0.35480(12) 0.44203(6) 0.38326(8) 0.0195(2) Uani 1 1 d . . . C7 C 0.28450(14) 0.45945(7) 0.28300(9) 0.0258(2) Uani 1 1 d . . . H7 H 0.3195(18) 0.4341(9) 0.2233(12) 0.030(4) Uiso 1 1 d . . . C8 C 0.15760(14) 0.51116(8) 0.27359(10) 0.0299(3) Uani 1 1 d . . . H8 H 0.105(2) 0.5228(10) 0.2041(14) 0.047(5) Uiso 1 1 d . . . C9 C 0.10591(14) 0.54384(7) 0.36408(10) 0.0284(3) Uani 1 1 d . . . H9 H 0.0175(18) 0.5788(9) 0.3607(11) 0.032(4) Uiso 1 1 d . . . C10 C 0.18425(13) 0.52342(7) 0.46043(9) 0.0242(2) Uani 1 1 d . . . H10 H 0.1497(17) 0.5454(8) 0.5246(11) 0.028(3) Uiso 1 1 d . . . C11 C 0.42249(13) 0.32581(6) 0.56853(8) 0.0201(2) Uani 1 1 d . . . C12 C 0.26401(14) 0.30266(7) 0.55157(9) 0.0243(2) Uani 1 1 d . . . H12 H 0.2162(18) 0.2980(8) 0.4799(12) 0.030(4) Uiso 1 1 d . . . C13 C 0.17804(15) 0.28657(7) 0.63817(10) 0.0279(2) Uani 1 1 d . . . H13 H 0.0674(19) 0.2709(9) 0.6263(11) 0.030(4) Uiso 1 1 d . . . C14 C 0.25182(16) 0.29351(7) 0.73952(9) 0.0295(3) Uani 1 1 d . . . H14 H 0.1926(19) 0.2834(9) 0.7992(12) 0.037(4) Uiso 1 1 d . . . C15 C 0.41059(15) 0.31649(7) 0.75502(9) 0.0285(3) Uani 1 1 d . . . H15 H 0.462(2) 0.3229(9) 0.8274(13) 0.042(4) Uiso 1 1 d . . . C16 C 0.49778(14) 0.33338(7) 0.66925(9) 0.0242(2) Uani 1 1 d . . . H16 H 0.6087(18) 0.3494(8) 0.6777(11) 0.028(3) Uiso 1 1 d . . . C17 C 0.73931(14) 0.48631(7) 0.05851(9) 0.0249(2) Uani 1 1 d . . . C18 C 0.69159(16) 0.40945(7) 0.04756(9) 0.0304(3) Uani 1 1 d . . . H18 H 0.6930(19) 0.3856(10) -0.0207(13) 0.040(4) Uiso 1 1 d . . . C19 C 0.64642(15) 0.37196(7) 0.13551(9) 0.0276(3) Uani 1 1 d . . . H19 H 0.6156(18) 0.3188(9) 0.1303(11) 0.032(4) Uiso 1 1 d . . . C20 C 0.64763(12) 0.41160(6) 0.23159(8) 0.0200(2) Uani 1 1 d . . . C21 C 0.69359(14) 0.48803(7) 0.23232(9) 0.0234(2) Uani 1 1 d . . . H21 H 0.6952(17) 0.5182(9) 0.2985(12) 0.032(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0223(4) 0.0359(4) 0.0625(5) 0.0092(4) 0.0141(3) 0.0015(3) F2 0.0288(4) 0.0414(5) 0.0508(5) 0.0163(4) 0.0099(3) 0.0165(3) F3 0.0282(4) 0.0725(6) 0.0550(5) -0.0374(5) 0.0020(4) 0.0114(4) O 0.0503(6) 0.0282(5) 0.0232(4) 0.0008(3) 0.0099(4) -0.0115(4) N1 0.0182(4) 0.0202(4) 0.0203(4) 0.0019(3) 0.0029(3) 0.0029(3) N2 0.0181(4) 0.0219(4) 0.0248(4) 0.0010(3) 0.0029(3) 0.0029(3) N3 0.0194(4) 0.0210(4) 0.0230(4) -0.0012(3) 0.0034(3) -0.0004(3) N4 0.0355(5) 0.0207(5) 0.0227(5) 0.0001(4) 0.0030(4) -0.0015(4) C1 0.0664(10) 0.0304(7) 0.0315(7) 0.0052(5) 0.0087(7) -0.0166(7) C2 0.0198(5) 0.0257(6) 0.0295(6) -0.0008(4) 0.0038(4) 0.0023(4) C3 0.0182(5) 0.0201(5) 0.0232(5) -0.0009(4) 0.0020(4) 0.0003(4) C4 0.0179(5) 0.0193(5) 0.0206(5) -0.0019(4) 0.0019(4) -0.0006(4) C5 0.0190(5) 0.0195(5) 0.0187(5) 0.0000(4) 0.0008(4) -0.0011(4) C6 0.0175(5) 0.0193(5) 0.0221(5) 0.0011(4) 0.0034(4) -0.0001(4) C7 0.0231(5) 0.0325(6) 0.0220(5) 0.0022(5) 0.0031(4) 0.0042(5) C8 0.0245(6) 0.0377(7) 0.0272(6) 0.0076(5) 0.0007(5) 0.0065(5) C9 0.0210(5) 0.0266(6) 0.0379(6) 0.0038(5) 0.0045(5) 0.0063(4) C10 0.0204(5) 0.0222(5) 0.0306(6) -0.0037(4) 0.0059(4) -0.0001(4) C11 0.0224(5) 0.0175(5) 0.0210(5) 0.0023(4) 0.0054(4) 0.0028(4) C12 0.0246(5) 0.0246(5) 0.0239(5) -0.0004(4) 0.0036(4) -0.0017(4) C13 0.0265(6) 0.0261(6) 0.0324(6) -0.0008(5) 0.0096(5) -0.0033(5) C14 0.0362(6) 0.0274(6) 0.0266(6) 0.0037(4) 0.0134(5) 0.0028(5) C15 0.0346(6) 0.0303(6) 0.0208(5) 0.0016(4) 0.0036(5) 0.0056(5) C16 0.0236(5) 0.0252(5) 0.0239(5) 0.0010(4) 0.0020(4) 0.0034(4) C17 0.0289(6) 0.0249(5) 0.0215(5) 0.0014(4) 0.0056(4) -0.0027(4) C18 0.0424(7) 0.0282(6) 0.0217(5) -0.0059(4) 0.0088(5) -0.0087(5) C19 0.0353(6) 0.0228(6) 0.0256(6) -0.0040(4) 0.0079(5) -0.0075(5) C20 0.0183(5) 0.0215(5) 0.0204(5) -0.0001(4) 0.0036(4) 0.0007(4) C21 0.0288(6) 0.0214(5) 0.0202(5) -0.0014(4) 0.0027(4) 0.0011(4) _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 C2 1.3390(14) . ? F2 C2 1.3318(14) . ? F3 C2 1.3345(14) . ? O C17 1.3567(13) . ? O C1 1.4314(16) . ? N1 N2 1.3513(12) . ? N1 C5 1.3686(13) . ? N1 C11 1.4366(13) . ? N2 C3 1.3314(14) . ? N3 C10 1.3354(14) . ? N3 C6 1.3449(13) . ? N4 C17 1.3197(15) . ? N4 C21 1.3472(14) . ? C1 H1A 0.980(17) . ? C1 H1B 0.986(17) . ? C1 H1C 0.98(2) . ? C2 C3 1.4901(15) . ? C3 C4 1.4067(15) . ? C4 C5 1.3879(14) . ? C4 C20 1.4787(14) . ? C5 C6 1.4758(14) . ? C6 C7 1.3941(15) . ? C7 C8 1.3866(16) . ? C7 H7 0.945(15) . ? C8 C9 1.3843(17) . ? C8 H8 0.976(18) . ? C9 C10 1.3884(17) . ? C9 H9 0.954(16) . ? C10 H10 0.967(14) . ? C11 C12 1.3824(16) . ? C11 C16 1.3877(15) . ? C12 C13 1.3915(16) . ? C12 H12 0.969(15) . ? C13 C14 1.3890(18) . ? C13 H13 0.963(15) . ? C14 C15 1.3825(18) . ? C14 H14 0.956(16) . ? C15 C16 1.3916(16) . ? C15 H15 0.990(17) . ? C16 H16 0.964(15) . ? C17 C18 1.3972(16) . ? C18 C19 1.3742(16) . ? C18 H18 0.963(16) . ? C19 C20 1.4031(15) . ? C19 H19 0.960(16) . ? C20 C21 1.3821(15) . ? C21 H21 0.991(15) . ? 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 C17 O C1 116.29(10) . . ? N2 N1 C5 112.74(9) . . ? N2 N1 C11 116.77(8) . . ? C5 N1 C11 130.40(9) . . ? C3 N2 N1 103.79(8) . . ? C10 N3 C6 116.91(10) . . ? C17 N4 C21 117.15(10) . . ? O C1 H1A 108.6(10) . . ? O C1 H1B 104.8(10) . . ? H1A C1 H1B 110.1(13) . . ? O C1 H1C 113.0(11) . . ? H1A C1 H1C 110.2(14) . . ? H1B C1 H1C 110.0(15) . . ? F2 C2 F3 106.97(10) . . ? F2 C2 F1 106.08(9) . . ? F3 C2 F1 105.92(10) . . ? F2 C2 C3 112.49(9) . . ? F3 C2 C3 112.88(9) . . ? F1 C2 C3 111.99(9) . . ? N2 C3 C4 113.24(9) . . ? N2 C3 C2 118.91(10) . . ? C4 C3 C2 127.79(10) . . ? C5 C4 C3 103.72(9) . . ? C5 C4 C20 129.64(10) . . ? C3 C4 C20 126.44(9) . . ? N1 C5 C4 106.51(9) . . ? N1 C5 C6 123.62(9) . . ? C4 C5 C6 129.86(10) . . ? N3 C6 C7 123.07(10) . . ? N3 C6 C5 117.16(9) . . ? C7 C6 C5 119.78(9) . . ? C8 C7 C6 118.79(11) . . ? C8 C7 H7 121.1(9) . . ? C6 C7 H7 120.0(9) . . ? C9 C8 C7 118.77(11) . . ? C9 C8 H8 121.4(10) . . ? C7 C8 H8 119.8(10) . . ? C8 C9 C10 118.31(11) . . ? C8 C9 H9 121.0(9) . . ? C10 C9 H9 120.6(9) . . ? N3 C10 C9 124.16(11) . . ? N3 C10 H10 116.2(9) . . ? C9 C10 H10 119.7(9) . . ? C12 C11 C16 121.85(10) . . ? C12 C11 N1 119.77(10) . . ? C16 C11 N1 118.30(10) . . ? C11 C12 C13 118.87(11) . . ? C11 C12 H12 119.1(9) . . ? C13 C12 H12 122.0(9) . . ? C14 C13 C12 120.02(11) . . ? C14 C13 H13 121.1(9) . . ? C12 C13 H13 118.8(9) . . ? C15 C14 C13 120.34(11) . . ? C15 C14 H14 119.4(9) . . ? C13 C14 H14 120.2(10) . . ? C14 C15 C16 120.32(11) . . ? C14 C15 H15 120.2(10) . . ? C16 C15 H15 119.4(10) . . ? C11 C16 C15 118.60(11) . . ? C11 C16 H16 119.3(8) . . ? C15 C16 H16 122.1(8) . . ? N4 C17 O 119.31(10) . . ? N4 C17 C18 124.12(10) . . ? O C17 C18 116.56(10) . . ? C19 C18 C17 117.81(11) . . ? C19 C18 H18 123.7(10) . . ? C17 C18 H18 118.5(10) . . ? C18 C19 C20 119.63(11) . . ? C18 C19 H19 119.3(9) . . ? C20 C19 H19 121.0(9) . . ? C21 C20 C19 117.38(10) . . ? C21 C20 C4 120.73(10) . . ? C19 C20 C4 121.78(10) . . ? N4 C21 C20 123.88(10) . . ? N4 C21 H21 116.2(9) . . ? C20 C21 H21 119.9(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.345 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.041 #===================================END #===================================END data_27 _database_code_depnum_ccdc_archive 'CCDC 699843' _database_code_CSD 699843 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-chloro-5-(trifluoromethyl)-4-pyridylboronic acid ; _chemical_name_common '2-chloro-5-(trifluoromethyl)-4-pyridylboronic acid' _chemical_melting_point 421.7(7) _chemical_formula_moiety 'C6 H4 B Cl F3 N O2' _chemical_formula_sum 'C6 H4 B Cl F3 N O2' _chemical_formula_weight 225.36 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' B B 0.0013 0.0007 '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 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 24.080(4) _cell_length_b 7.8042(12) _cell_length_c 9.3848(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.42(3) _cell_angle_gamma 90.00 _cell_volume 1752.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6018 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 29.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.454 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8597 _exptl_absorpt_correction_T_max 0.9370 _exptl_absorpt_process_details 'XPREP 6.14 (Bruker, 2003), R(int)=0.039 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.0800 -1.00 0.00 0.00 0.0800 2.00 0.00 -3.00 0.1000 -2.00 0.00 3.00 0.1000 0.00 -1.00 0.00 0.2000 1.00 1.00 0.00 0.1800 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 3 runs of narrow-frame \w-scans (scan width 0.3\% \w, 20s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 9857 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 29.01 _reflns_number_total 2339 _reflns_number_gt 2001 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0362P)^2^+0.8943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2339 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Cl Cl 0.732310(13) 0.54159(4) 0.93793(3) 0.02831(10) Uani 1 1 d . . . F1 F 0.52398(3) 0.09766(10) 0.61807(10) 0.0351(2) Uani 1 1 d . . . F2 F 0.54110(3) 0.24639(11) 0.43455(8) 0.0343(2) Uani 1 1 d . . . F3 F 0.49355(3) 0.35561(10) 0.59217(8) 0.03192(18) Uani 1 1 d . . . O1 O 0.63980(4) -0.09015(10) 0.81552(9) 0.02208(18) Uani 1 1 d . . . H01 H 0.6388(8) -0.195(3) 0.801(2) 0.044(5) Uiso 1 1 d . . . O2 O 0.62803(4) -0.07843(10) 0.56447(9) 0.02434(19) Uani 1 1 d . . . H02 H 0.6266(8) -0.021(2) 0.499(2) 0.045(5) Uiso 1 1 d . . . N1 N 0.63885(4) 0.55963(12) 0.77106(11) 0.0211(2) Uani 1 1 d . . . C1 C 0.53750(5) 0.25419(15) 0.57551(13) 0.0234(2) Uani 1 1 d . . . C2 C 0.67806(5) 0.45195(13) 0.82504(12) 0.0178(2) Uani 1 1 d . . . C3 C 0.67767(5) 0.27671(13) 0.79935(12) 0.0172(2) Uani 1 1 d . . . H3 H 0.7062(6) 0.2096(19) 0.8425(16) 0.022(3) Uiso 1 1 d . . . C4 C 0.63254(4) 0.20507(13) 0.71381(11) 0.0157(2) Uani 1 1 d . . . C5 C 0.59026(4) 0.31816(13) 0.65984(12) 0.0180(2) Uani 1 1 d . . . C6 C 0.59523(5) 0.49256(14) 0.68887(13) 0.0229(2) Uani 1 1 d . . . H6 H 0.5678(6) 0.572(2) 0.6543(17) 0.028(4) Uiso 1 1 d . . . B B 0.63245(5) 0.00167(15) 0.69174(13) 0.0171(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.03003(16) 0.01889(14) 0.03299(17) -0.00306(11) -0.00986(12) -0.00545(10) F1 0.0333(4) 0.0244(4) 0.0453(5) -0.0016(3) -0.0061(3) -0.0112(3) F2 0.0337(4) 0.0464(5) 0.0212(4) -0.0105(3) -0.0034(3) -0.0025(3) F3 0.0235(3) 0.0359(4) 0.0346(4) -0.0080(3) -0.0046(3) 0.0062(3) O1 0.0423(5) 0.0091(3) 0.0145(4) -0.0008(3) 0.0017(3) 0.0003(3) O2 0.0466(5) 0.0129(4) 0.0134(4) -0.0007(3) 0.0030(4) -0.0006(3) N1 0.0286(5) 0.0112(4) 0.0224(5) -0.0004(3) -0.0025(4) 0.0007(3) C1 0.0246(5) 0.0211(5) 0.0234(6) -0.0039(4) -0.0028(4) 0.0000(4) C2 0.0223(5) 0.0130(5) 0.0175(5) -0.0006(4) -0.0007(4) -0.0030(4) C3 0.0226(5) 0.0122(4) 0.0163(5) 0.0009(4) -0.0001(4) 0.0012(4) C4 0.0232(5) 0.0111(4) 0.0129(4) 0.0007(3) 0.0030(4) -0.0005(4) C5 0.0218(5) 0.0140(5) 0.0176(5) -0.0016(4) -0.0009(4) -0.0003(4) C6 0.0283(6) 0.0134(5) 0.0251(6) -0.0012(4) -0.0052(4) 0.0045(4) B 0.0240(6) 0.0109(5) 0.0166(5) -0.0005(4) 0.0027(4) -0.0007(4) _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 Cl C2 1.7345(12) . ? F1 C1 1.3368(14) . ? F2 C1 1.3367(15) . ? F3 C1 1.3447(14) . ? O1 B 1.3595(14) . ? O1 H01 0.826(19) . ? O2 B 1.3418(14) . ? O2 H02 0.76(2) . ? N1 C2 1.3219(14) . ? N1 C6 1.3384(16) . ? C1 C5 1.5048(16) . ? C2 C3 1.3886(14) . ? C3 C4 1.3938(15) . ? C3 H3 0.921(15) . ? C4 C5 1.3988(15) . ? C4 B 1.6008(15) . ? C5 C6 1.3906(15) . ? C6 H6 0.937(15) . ? 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 B O1 H01 112.4(13) . . ? B O2 H02 116.0(14) . . ? C2 N1 C6 116.95(9) . . ? F2 C1 F1 107.39(10) . . ? F2 C1 F3 106.31(10) . . ? F1 C1 F3 106.38(10) . . ? F2 C1 C5 113.04(10) . . ? F1 C1 C5 111.44(10) . . ? F3 C1 C5 111.89(10) . . ? N1 C2 C3 124.67(10) . . ? N1 C2 Cl 115.76(8) . . ? C3 C2 Cl 119.56(9) . . ? C2 C3 C4 119.00(10) . . ? C2 C3 H3 119.6(9) . . ? C4 C3 H3 121.3(9) . . ? C3 C4 C5 116.39(9) . . ? C3 C4 B 117.51(9) . . ? C5 C4 B 126.05(10) . . ? C6 C5 C4 120.23(10) . . ? C6 C5 C1 118.47(10) . . ? C4 C5 C1 121.24(10) . . ? N1 C6 C5 122.71(10) . . ? N1 C6 H6 114.6(9) . . ? C5 C6 H6 122.6(10) . . ? O2 B O1 120.32(10) . . ? O2 B C4 125.17(10) . . ? O1 B C4 114.45(9) . . ? 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 N1 C2 C3 1.74(17) . . . . ? C6 N1 C2 Cl -177.03(9) . . . . ? N1 C2 C3 C4 -1.69(17) . . . . ? Cl C2 C3 C4 177.03(8) . . . . ? C2 C3 C4 C5 -0.16(15) . . . . ? C2 C3 C4 B -177.65(10) . . . . ? C3 C4 C5 C6 1.78(16) . . . . ? B C4 C5 C6 179.03(11) . . . . ? C3 C4 C5 C1 -175.35(10) . . . . ? B C4 C5 C1 1.90(17) . . . . ? F2 C1 C5 C6 92.71(13) . . . . ? F1 C1 C5 C6 -146.24(11) . . . . ? F3 C1 C5 C6 -27.27(15) . . . . ? F2 C1 C5 C4 -90.11(13) . . . . ? F1 C1 C5 C4 30.94(15) . . . . ? F3 C1 C5 C4 149.91(10) . . . . ? C2 N1 C6 C5 0.03(18) . . . . ? C4 C5 C6 N1 -1.81(18) . . . . ? C1 C5 C6 N1 175.40(11) . . . . ? C3 C4 B O2 -124.69(13) . . . . ? C5 C4 B O2 58.09(17) . . . . ? C3 C4 B O1 52.59(14) . . . . ? C5 C4 B O1 -124.63(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H01 N1 0.826(19) 1.94(2) 2.7646(13) 178.1(19) 1_545 O2 H02 O1 0.76(2) 1.98(2) 2.7236(12) 165(2) 6 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.416 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.047