# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p21n _database_code_depnum_ccdc_archive 'CCDC 900469' #TrackingRef 'JK-C-11.cif' #============================================================================== # JK-C-11-2 #============================================================================== _audit_creation_date '19 June 2012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 F3 N4 O2' _chemical_formula_sum 'C14 H13 F3 N4 O2' _chemical_formula_weight 326.28 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0135(7) _cell_length_b 15.0651(13) _cell_length_c 22.7939(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.2910(10) _cell_angle_gamma 90.00 _cell_volume 2751.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 3802 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.39 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 12930 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4837 _reflns_number_gt 4044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0464P)^2^+1.4805P] 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 4837 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.6761(2) 0.71102(12) 0.84399(8) 0.0163(4) Uani 1 1 d . . . C2 C 0.6978(2) 0.63356(12) 0.87860(8) 0.0158(4) Uani 1 1 d . . . C3 C 0.6218(2) 0.65166(12) 0.93256(8) 0.0154(4) Uani 1 1 d . . . C4 C 0.5977(2) 0.60410(12) 0.98592(8) 0.0170(4) Uani 1 1 d . . . H4 H 0.6393 0.5453 0.9896 0.020 Uiso 1 1 calc R . . C5 C 0.5160(2) 0.64186(12) 1.03153(8) 0.0183(4) Uani 1 1 d . . . H5 H 0.4994 0.6101 1.0670 0.022 Uiso 1 1 calc R . . C6 C 0.4556(2) 0.73037(12) 1.02492(8) 0.0162(4) Uani 1 1 d . . . C7 C 0.3702(2) 0.79333(12) 1.05968(8) 0.0171(4) Uani 1 1 d . . . C8 C 0.4784(2) 0.77582(12) 0.97267(8) 0.0155(4) Uani 1 1 d . . . C9 C 0.7284(3) 0.72818(13) 0.78246(8) 0.0207(4) Uani 1 1 d . . . H9A H 0.7024 0.7897 0.7720 0.031 Uiso 1 1 calc R . . H9B H 0.6685 0.6879 0.7560 0.031 Uiso 1 1 calc R . . H9C H 0.8488 0.7182 0.7789 0.031 Uiso 1 1 calc R . . C10 C 0.4058(3) 0.93069(12) 0.93466(8) 0.0224(4) Uani 1 1 d . . . H10A H 0.5173 0.9570 0.9318 0.034 Uiso 1 1 calc R . . H10B H 0.3263 0.9758 0.9478 0.034 Uiso 1 1 calc R . . H10C H 0.3714 0.9082 0.8961 0.034 Uiso 1 1 calc R . . C11 C 0.7776(2) 0.54846(12) 0.86470(8) 0.0167(4) Uani 1 1 d . . . C12 C 0.9136(3) 0.46208(12) 0.79278(8) 0.0203(4) Uani 1 1 d . . . H12A H 0.8301 0.4137 0.7946 0.024 Uiso 1 1 calc R . . H12B H 1.0072 0.4473 0.8196 0.024 Uiso 1 1 calc R . . C13 C 0.9761(3) 0.47284(14) 0.73089(9) 0.0250(5) Uani 1 1 d . . . H13A H 0.8822 0.4868 0.7048 0.037 Uiso 1 1 calc R . . H13B H 1.0289 0.4175 0.7181 0.037 Uiso 1 1 calc R . . H13C H 1.0579 0.5212 0.7296 0.037 Uiso 1 1 calc R . . C14 C 0.3181(2) 0.78372(12) 1.12198(8) 0.0185(4) Uani 1 1 d . . . C1B C 0.1765(2) 0.71631(12) 0.83833(8) 0.0166(4) Uani 1 1 d . . . C2B C 0.1893(2) 0.64084(12) 0.87549(8) 0.0153(4) Uani 1 1 d . . . C3B C 0.1090(2) 0.66405(12) 0.92772(8) 0.0156(4) Uani 1 1 d . . . C4B C 0.0752(2) 0.62141(12) 0.98219(8) 0.0169(4) Uani 1 1 d . . . H4B H 0.1102 0.5618 0.9881 0.020 Uiso 1 1 calc R . . C5B C -0.0060(2) 0.66446(12) 1.02580(8) 0.0168(4) Uani 1 1 d . . . H5B H -0.0283 0.6358 1.0620 0.020 Uiso 1 1 calc R . . C6B C -0.0576(2) 0.75465(12) 1.01578(8) 0.0155(4) Uani 1 1 d . . . C7B C -0.1378(2) 0.82316(12) 1.04721(8) 0.0170(4) Uani 1 1 d . . . C8B C -0.0272(2) 0.79429(12) 0.96209(8) 0.0152(4) Uani 1 1 d . . . C9B C 0.2358(3) 0.72830(13) 0.77692(8) 0.0215(4) Uani 1 1 d . . . H9B1 H 0.1751 0.6877 0.7509 0.032 Uiso 1 1 calc R . . H9B2 H 0.3556 0.7154 0.7751 0.032 Uiso 1 1 calc R . . H9B3 H 0.2158 0.7897 0.7645 0.032 Uiso 1 1 calc R . . C10B C -0.0974(3) 0.94379(12) 0.91504(8) 0.0212(4) Uani 1 1 d . . . H10D H 0.0149 0.9560 0.9002 0.032 Uiso 1 1 calc R . . H10E H -0.1466 0.9988 0.9301 0.032 Uiso 1 1 calc R . . H10F H -0.1672 0.9205 0.8832 0.032 Uiso 1 1 calc R . . C11B C 0.2646(2) 0.55387(12) 0.86496(8) 0.0169(4) Uani 1 1 d . . . C12B C 0.4107(3) 0.46199(12) 0.79872(8) 0.0198(4) Uani 1 1 d . . . H12C H 0.3282 0.4134 0.8026 0.024 Uiso 1 1 calc R . . H12D H 0.5038 0.4507 0.8264 0.024 Uiso 1 1 calc R . . C13B C 0.4746(3) 0.46652(13) 0.73674(8) 0.0232(4) Uani 1 1 d . . . H13D H 0.3811 0.4770 0.7098 0.035 Uiso 1 1 calc R . . H13E H 0.5291 0.4103 0.7267 0.035 Uiso 1 1 calc R . . H13F H 0.5552 0.5152 0.7334 0.035 Uiso 1 1 calc R . . C14B C -0.1877(2) 0.82568(12) 1.11009(8) 0.0192(4) Uani 1 1 d . . . F1 F 0.43362(14) 0.73979(8) 1.15374(5) 0.0270(3) Uani 1 1 d . . . F2 F 0.17599(14) 0.73718(7) 1.12828(5) 0.0236(3) Uani 1 1 d . . . F3 F 0.29391(15) 0.86233(7) 1.14798(5) 0.0266(3) Uani 1 1 d . . . F1B F -0.21110(15) 0.74385(7) 1.13147(5) 0.0251(3) Uani 1 1 d . . . F2B F -0.07133(14) 0.86445(8) 1.14442(5) 0.0259(3) Uani 1 1 d . . . F3B F -0.32852(14) 0.87232(7) 1.11868(5) 0.0237(3) Uani 1 1 d . . . N1 N 0.5942(2) 0.77445(10) 0.87306(6) 0.0169(3) Uani 1 1 d . . . N2 N 0.56162(19) 0.73712(10) 0.92695(6) 0.0148(3) Uani 1 1 d . . . N3 N 0.4094(2) 0.85744(10) 0.97682(6) 0.0170(3) Uani 1 1 d . . . N4 N 0.3425(2) 0.86896(10) 1.03137(7) 0.0189(4) Uani 1 1 d . . . N1B N 0.0962(2) 0.78320(10) 0.86424(7) 0.0175(4) Uani 1 1 d . . . N2B N 0.05610(19) 0.75021(10) 0.91865(6) 0.0149(3) Uani 1 1 d . . . N3B N -0.0874(2) 0.87828(10) 0.96232(6) 0.0169(3) Uani 1 1 d . . . N4B N -0.1564(2) 0.89660(10) 1.01542(7) 0.0183(4) Uani 1 1 d . . . O1 O 0.78706(18) 0.48626(9) 0.89841(6) 0.0240(3) Uani 1 1 d . . . O2 O 0.83803(16) 0.54625(8) 0.80968(5) 0.0184(3) Uani 1 1 d . . . O1B O 0.26492(18) 0.49341(9) 0.90027(6) 0.0243(3) Uani 1 1 d . . . O2B O 0.33289(16) 0.54722(8) 0.81132(5) 0.0185(3) 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 C1 0.0178(10) 0.0141(10) 0.0171(10) -0.0012(7) 0.0004(8) -0.0015(7) C2 0.0190(10) 0.0113(9) 0.0170(9) -0.0019(7) -0.0007(8) -0.0002(7) C3 0.0169(10) 0.0109(9) 0.0183(10) -0.0014(7) -0.0016(8) -0.0010(7) C4 0.0217(10) 0.0116(9) 0.0178(10) 0.0013(7) -0.0006(8) 0.0000(7) C5 0.0250(11) 0.0143(10) 0.0154(9) 0.0027(8) -0.0003(8) -0.0007(8) C6 0.0180(10) 0.0153(9) 0.0152(9) -0.0006(8) -0.0003(8) -0.0013(7) C7 0.0188(10) 0.0151(10) 0.0174(10) -0.0014(8) 0.0001(8) 0.0003(8) C8 0.0160(10) 0.0132(9) 0.0173(9) -0.0016(7) 0.0006(7) -0.0008(7) C9 0.0286(11) 0.0165(10) 0.0169(10) 0.0007(8) 0.0031(8) 0.0030(8) C10 0.0335(12) 0.0126(10) 0.0212(10) 0.0032(8) 0.0047(9) 0.0064(8) C11 0.0198(10) 0.0131(10) 0.0172(10) -0.0021(8) -0.0018(8) -0.0007(7) C12 0.0246(11) 0.0132(10) 0.0232(10) -0.0037(8) 0.0010(8) 0.0035(8) C13 0.0303(12) 0.0212(11) 0.0234(10) -0.0045(9) 0.0031(9) 0.0030(9) C14 0.0224(11) 0.0150(10) 0.0180(10) -0.0023(8) 0.0011(8) 0.0002(8) C1B 0.0188(10) 0.0142(10) 0.0168(9) -0.0006(7) -0.0001(8) -0.0001(7) C2B 0.0185(10) 0.0129(9) 0.0145(9) -0.0007(7) -0.0013(7) 0.0003(7) C3B 0.0172(10) 0.0100(9) 0.0194(10) -0.0012(7) -0.0045(8) -0.0007(7) C4B 0.0218(10) 0.0116(9) 0.0172(9) 0.0006(7) -0.0018(8) 0.0008(8) C5B 0.0207(10) 0.0144(10) 0.0152(9) 0.0011(7) -0.0005(8) -0.0012(8) C6B 0.0162(10) 0.0152(10) 0.0152(9) -0.0011(8) 0.0000(7) -0.0011(7) C7B 0.0192(10) 0.0139(10) 0.0178(10) -0.0008(8) 0.0004(8) -0.0018(8) C8B 0.0169(10) 0.0106(9) 0.0181(10) -0.0020(7) 0.0003(8) -0.0009(7) C9B 0.0306(12) 0.0164(10) 0.0176(10) 0.0017(8) 0.0039(8) 0.0031(8) C10B 0.0297(11) 0.0138(10) 0.0200(10) 0.0026(8) 0.0035(8) 0.0032(8) C11B 0.0187(10) 0.0158(10) 0.0161(10) -0.0008(8) -0.0027(8) 0.0014(8) C12B 0.0247(11) 0.0133(9) 0.0213(10) -0.0021(8) 0.0005(8) 0.0040(8) C13B 0.0277(11) 0.0195(10) 0.0225(10) -0.0031(8) 0.0036(8) 0.0036(9) C14B 0.0215(11) 0.0158(10) 0.0202(10) -0.0026(8) 0.0006(8) 0.0021(8) F1 0.0271(7) 0.0357(7) 0.0181(6) 0.0054(5) 0.0002(5) 0.0059(5) F2 0.0246(6) 0.0251(6) 0.0212(6) 0.0006(5) 0.0034(5) -0.0044(5) F3 0.0409(8) 0.0185(6) 0.0206(6) -0.0060(5) 0.0083(5) -0.0018(5) F1B 0.0371(7) 0.0166(6) 0.0215(6) 0.0029(5) 0.0086(5) 0.0016(5) F2B 0.0276(7) 0.0294(7) 0.0207(6) -0.0059(5) -0.0014(5) -0.0003(5) F3B 0.0248(6) 0.0235(6) 0.0229(6) -0.0016(5) 0.0056(5) 0.0061(5) N1 0.0234(9) 0.0145(8) 0.0129(8) 0.0013(6) 0.0008(6) 0.0010(7) N2 0.0189(8) 0.0114(8) 0.0141(8) 0.0002(6) 0.0009(6) 0.0002(6) N3 0.0232(9) 0.0122(8) 0.0156(8) 0.0009(6) 0.0018(7) 0.0035(7) N4 0.0222(9) 0.0171(8) 0.0176(8) -0.0017(7) 0.0025(7) 0.0021(7) N1B 0.0245(9) 0.0135(8) 0.0144(8) 0.0019(6) 0.0029(7) 0.0006(7) N2B 0.0201(9) 0.0116(8) 0.0131(8) -0.0005(6) 0.0004(6) 0.0007(6) N3B 0.0233(9) 0.0117(8) 0.0156(8) 0.0007(6) 0.0038(7) 0.0019(7) N4B 0.0226(9) 0.0153(8) 0.0170(8) -0.0016(7) 0.0025(7) 0.0016(7) O1 0.0360(9) 0.0147(7) 0.0213(7) 0.0020(6) 0.0040(6) 0.0055(6) O2 0.0256(8) 0.0131(7) 0.0165(7) -0.0024(5) 0.0033(6) 0.0037(5) O1B 0.0379(9) 0.0155(7) 0.0195(7) 0.0022(6) 0.0037(6) 0.0079(6) O2B 0.0274(8) 0.0123(7) 0.0159(7) -0.0017(5) 0.0040(6) 0.0042(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 C1 N1 1.337(2) . ? C1 C2 1.419(3) . ? C1 C9 1.489(2) . ? C2 C3 1.402(3) . ? C2 C11 1.468(3) . ? C3 N2 1.380(2) . ? C3 C4 1.426(3) . ? C4 C5 1.356(3) . ? C4 H4 0.9500 . ? C5 C6 1.426(3) . ? C5 H5 0.9500 . ? C6 C8 1.387(3) . ? C6 C7 1.415(3) . ? C7 N4 1.328(2) . ? C7 C14 1.489(3) . ? C8 N3 1.352(2) . ? C8 N2 1.370(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N3 1.463(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O1 1.214(2) . ? C11 O2 1.347(2) . ? C12 O2 1.458(2) . ? C12 C13 1.508(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 F3 1.339(2) . ? C14 F2 1.345(2) . ? C14 F1 1.346(2) . ? C1B N1B 1.335(2) . ? C1B C2B 1.421(3) . ? C1B C9B 1.491(3) . ? C2B C3B 1.400(3) . ? C2B C11B 1.463(3) . ? C3B N2B 1.381(2) . ? C3B C4B 1.425(3) . ? C4B C5B 1.356(3) . ? C4B H4B 0.9500 . ? C5B C6B 1.438(3) . ? C5B H5B 0.9500 . ? C6B C8B 1.385(3) . ? C6B C7B 1.413(3) . ? C7B N4B 1.330(2) . ? C7B C14B 1.491(3) . ? C8B N3B 1.354(2) . ? C8B N2B 1.369(2) . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? C10B N3B 1.463(2) . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B O1B 1.215(2) . ? C11B O2B 1.346(2) . ? C12B O2B 1.457(2) . ? C12B C13B 1.507(3) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C14B F1B 1.339(2) . ? C14B F3B 1.344(2) . ? C14B F2B 1.348(2) . ? N1 N2 1.377(2) . ? N3 N4 1.368(2) . ? N1B N2B 1.376(2) . ? N3B N4B 1.362(2) . ? 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 N1 C1 C2 111.81(16) . . ? N1 C1 C9 118.96(16) . . ? C2 C1 C9 129.23(17) . . ? C3 C2 C1 105.98(16) . . ? C3 C2 C11 123.43(16) . . ? C1 C2 C11 130.58(17) . . ? N2 C3 C2 104.66(15) . . ? N2 C3 C4 119.94(16) . . ? C2 C3 C4 135.40(17) . . ? C5 C4 C3 120.73(17) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.44(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C8 C6 C7 102.49(16) . . ? C8 C6 C5 120.40(17) . . ? C7 C6 C5 137.11(17) . . ? N4 C7 C6 112.55(16) . . ? N4 C7 C14 119.99(16) . . ? C6 C7 C14 127.42(17) . . ? N3 C8 N2 129.87(17) . . ? N3 C8 C6 109.46(16) . . ? N2 C8 C6 120.66(17) . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C11 O2 123.27(17) . . ? O1 C11 C2 124.29(17) . . ? O2 C11 C2 112.44(15) . . ? O2 C12 C13 107.11(15) . . ? O2 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? O2 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F3 C14 F2 106.83(15) . . ? F3 C14 F1 107.30(15) . . ? F2 C14 F1 105.46(15) . . ? F3 C14 C7 112.20(15) . . ? F2 C14 C7 113.22(15) . . ? F1 C14 C7 111.39(15) . . ? N1B C1B C2B 111.93(16) . . ? N1B C1B C9B 118.72(16) . . ? C2B C1B C9B 129.34(17) . . ? C3B C2B C1B 105.97(16) . . ? C3B C2B C11B 123.69(16) . . ? C1B C2B C11B 130.33(16) . . ? N2B C3B C2B 104.44(15) . . ? N2B C3B C4B 119.65(16) . . ? C2B C3B C4B 135.91(17) . . ? C5B C4B C3B 121.12(17) . . ? C5B C4B H4B 119.4 . . ? C3B C4B H4B 119.4 . . ? C4B C5B C6B 118.32(17) . . ? C4B C5B H5B 120.8 . . ? C6B C5B H5B 120.8 . . ? C8B C6B C7B 102.46(16) . . ? C8B C6B C5B 119.73(17) . . ? C7B C6B C5B 137.81(17) . . ? N4B C7B C6B 112.42(16) . . ? N4B C7B C14B 118.21(16) . . ? C6B C7B C14B 129.14(17) . . ? N3B C8B N2B 129.13(16) . . ? N3B C8B C6B 109.59(16) . . ? N2B C8B C6B 121.26(16) . . ? C1B C9B H9B1 109.5 . . ? C1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N3B C10B H10D 109.5 . . ? N3B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? N3B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? O1B C11B O2B 123.13(17) . . ? O1B C11B C2B 124.19(17) . . ? O2B C11B C2B 112.68(15) . . ? O2B C12B C13B 107.02(15) . . ? O2B C12B H12C 110.3 . . ? C13B C12B H12C 110.3 . . ? O2B C12B H12D 110.3 . . ? C13B C12B H12D 110.3 . . ? H12C C12B H12D 108.6 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? F1B C14B F3B 108.01(15) . . ? F1B C14B F2B 106.58(15) . . ? F3B C14B F2B 105.53(14) . . ? F1B C14B C7B 111.42(15) . . ? F3B C14B C7B 112.52(16) . . ? F2B C14B C7B 112.39(16) . . ? C1 N1 N2 104.23(14) . . ? C8 N2 N1 126.85(15) . . ? C8 N2 C3 119.82(15) . . ? N1 N2 C3 113.32(14) . . ? C8 N3 N4 109.96(15) . . ? C8 N3 C10 130.28(15) . . ? N4 N3 C10 119.66(15) . . ? C7 N4 N3 105.53(15) . . ? C1B N1B N2B 103.97(14) . . ? C8B N2B N1B 126.43(15) . . ? C8B N2B C3B 119.88(15) . . ? N1B N2B C3B 113.69(14) . . ? C8B N3B N4B 109.82(14) . . ? C8B N3B C10B 130.21(15) . . ? N4B N3B C10B 119.80(15) . . ? C7B N4B N3B 105.71(15) . . ? C11 O2 C12 114.80(14) . . ? C11B O2B C12B 114.90(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.279 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.053