# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Aakeroy, C.' _publ_contact_author_email aakeroy@ksu.edu loop_ _publ_author_name C.Aakeroy P.Chopade C.Ganser J.Desper data_cg0902m _database_code_depnum_ccdc_archive 'CCDC 809428' #TrackingRef '- allrevised.cif' #A1B1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; P60 2-aminopyrazine, 4-I-F4-PhCOOH ; _chemical_name_common 'P60 2-aminopyrazine, 4-I-F4-PhCOOH' _chemical_melting_point ? _chemical_formula_moiety ; C4 H5 N3, C7 H I F4 O2 ; _chemical_formula_sum 'C11 H6 F4 I N3 O2' _chemical_formula_weight 415.09 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' I I -0.4742 1.8119 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 15.2832(8) _cell_length_b 11.5421(6) _cell_length_c 15.3499(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.171(2) _cell_angle_gamma 90.00 _cell_volume 2587.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9233 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 33.14 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 2.533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5589 _exptl_absorpt_correction_T_max 0.7181 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 41424 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 33.14 _reflns_number_total 9835 _reflns_number_gt 8674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9835 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.002 _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 I1_1 I 0.634407(8) 1.021263(11) -0.066748(7) 0.02070(4) Uani 1 1 d . . . C11_1 C 0.62284(12) 0.99959(15) 0.25052(11) 0.0176(3) Uani 1 1 d . . . C17_1 C 0.62144(12) 0.99115(15) 0.34894(12) 0.0192(3) Uani 1 1 d . . . O11_1 O 0.59532(10) 1.07915(12) 0.38325(8) 0.0241(3) Uani 1 1 d . . . O12_1 O 0.64693(11) 0.89740(13) 0.38793(9) 0.0289(3) Uani 1 1 d . . . C12_1 C 0.61137(13) 0.90121(16) 0.19500(11) 0.0221(3) Uani 1 1 d . . . F12_1 F 0.59279(11) 0.79817(11) 0.22471(8) 0.0362(3) Uani 1 1 d . . . C13_1 C 0.61572(13) 0.90710(16) 0.10616(11) 0.0223(3) Uani 1 1 d . . . F13_1 F 0.60336(11) 0.80870(11) 0.05698(8) 0.0371(3) Uani 1 1 d . . . C14_1 C 0.63097(12) 1.01070(15) 0.06775(11) 0.0181(3) Uani 1 1 d . . . C15_1 C 0.64180(11) 1.10826(15) 0.12185(11) 0.0181(3) Uani 1 1 d . . . F15_1 F 0.65732(9) 1.21133(10) 0.08882(7) 0.0271(2) Uani 1 1 d . . . C16_1 C 0.63766(11) 1.10330(15) 0.21069(11) 0.0178(3) Uani 1 1 d . . . F16_1 F 0.65270(8) 1.20193(10) 0.25899(7) 0.0247(2) Uani 1 1 d . . . N21_1 N 0.60914(10) 1.06390(14) 0.56103(10) 0.0192(3) Uani 1 1 d . . . H21_1 H 0.6023(16) 1.068(2) 0.5003(16) 0.023 Uiso 1 1 d . . . C22_1 C 0.61893(11) 0.95913(16) 0.60113(11) 0.0196(3) Uani 1 1 d . . . N22_1 N 0.62162(12) 0.86500(15) 0.55372(11) 0.0258(3) Uani 1 1 d . . . H22A_1 H 0.6265(18) 0.869(3) 0.4963(18) 0.031 Uiso 1 1 d . . . H22B_1 H 0.6348(18) 0.799(3) 0.5837(17) 0.031 Uiso 1 1 d . . . C23_1 C 0.62545(13) 0.95710(19) 0.69631(12) 0.0256(4) Uani 1 1 d . . . H23_1 H 0.6304 0.8844 0.7264 0.031 Uiso 1 1 calc R . . N24_1 N 0.62486(12) 1.05071(18) 0.74295(10) 0.0294(3) Uani 1 1 d . . . C25_1 C 0.61548(14) 1.15546(19) 0.69979(13) 0.0282(4) Uani 1 1 d . . . H25_1 H 0.6146 1.2243 0.7334 0.034 Uiso 1 1 calc R . . C26_1 C 0.60734(12) 1.16242(17) 0.60891(12) 0.0229(3) Uani 1 1 d . . . H26_1 H 0.6005 1.2356 0.5794 0.027 Uiso 1 1 calc R . . I2_2 I -0.078881(7) 0.496643(10) 0.368010(7) 0.01892(3) Uani 1 1 d . . . C11_2 C 0.24357(11) 0.46888(15) 0.36977(11) 0.0174(3) Uani 1 1 d . . . C17_2 C 0.34436(11) 0.46012(16) 0.37454(12) 0.0193(3) Uani 1 1 d . . . O11_2 O 0.38539(9) 0.55149(13) 0.36681(12) 0.0314(3) Uani 1 1 d . . . O12_2 O 0.37936(10) 0.36203(14) 0.38628(13) 0.0357(4) Uani 1 1 d . . . C12_2 C 0.18571(11) 0.37305(16) 0.35081(12) 0.0205(3) Uani 1 1 d . . . F12_2 F 0.21496(8) 0.26924(11) 0.33192(9) 0.0320(3) Uani 1 1 d . . . C13_2 C 0.09446(11) 0.37998(16) 0.34886(12) 0.0206(3) Uani 1 1 d . . . F13_2 F 0.04397(8) 0.28306(11) 0.32988(9) 0.0323(3) Uani 1 1 d . . . C14_2 C 0.05605(11) 0.48336(15) 0.36510(12) 0.0181(3) Uani 1 1 d . . . C15_2 C 0.11309(12) 0.57928(16) 0.38337(13) 0.0218(3) Uani 1 1 d . . . F15_2 F 0.08084(8) 0.68145(11) 0.40055(10) 0.0360(3) Uani 1 1 d . . . C16_2 C 0.20385(12) 0.57228(16) 0.38557(12) 0.0213(3) Uani 1 1 d . . . F16_2 F 0.25298(8) 0.66983(11) 0.40731(10) 0.0358(3) Uani 1 1 d . . . N21_2 N 0.56060(10) 0.52515(13) 0.38211(10) 0.0191(3) Uani 1 1 d . . . H21_2 H 0.5012(18) 0.524(2) 0.3797(17) 0.023 Uiso 1 1 d . . . C22_2 C 0.60157(11) 0.42143(15) 0.38290(11) 0.0181(3) Uani 1 1 d . . . N22_2 N 0.55652(11) 0.32444(15) 0.38374(12) 0.0246(3) Uani 1 1 d . . . H22A_2 H 0.5009(18) 0.328(3) 0.3802(16) 0.030 Uiso 1 1 d . . . H22B_2 H 0.5837(17) 0.253(3) 0.3772(17) 0.030 Uiso 1 1 d . . . C23_2 C 0.69508(12) 0.42338(17) 0.38349(12) 0.0220(3) Uani 1 1 d . . . H23_2 H 0.7257 0.3518 0.3831 0.026 Uiso 1 1 calc R . . N24_2 N 0.74020(11) 0.51939(15) 0.38452(11) 0.0239(3) Uani 1 1 d . . . C25_2 C 0.69699(12) 0.62227(17) 0.38402(13) 0.0240(3) Uani 1 1 d . . . H25_2 H 0.7294 0.6927 0.3847 0.029 Uiso 1 1 calc R . . C26_2 C 0.60731(12) 0.62523(16) 0.38248(12) 0.0214(3) Uani 1 1 d . . . H26_2 H 0.5775 0.6976 0.3817 0.026 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 I1_1 0.02373(6) 0.02409(6) 0.01599(5) 0.00061(4) 0.00852(4) 0.00171(4) C11_1 0.0204(7) 0.0175(7) 0.0157(6) -0.0005(5) 0.0068(6) 0.0004(5) C17_1 0.0203(7) 0.0197(8) 0.0182(7) -0.0001(5) 0.0065(6) -0.0011(6) O11_1 0.0362(7) 0.0206(6) 0.0187(5) 0.0011(5) 0.0131(5) 0.0049(5) O12_1 0.0474(8) 0.0207(6) 0.0209(5) 0.0029(5) 0.0135(6) 0.0068(6) C12_1 0.0327(9) 0.0157(7) 0.0195(7) 0.0004(6) 0.0102(6) -0.0038(6) F12_1 0.0710(9) 0.0175(5) 0.0232(5) 0.0001(4) 0.0186(5) -0.0111(6) C13_1 0.0334(9) 0.0162(7) 0.0191(7) -0.0026(6) 0.0104(6) -0.0005(6) F13_1 0.0717(9) 0.0178(5) 0.0251(5) -0.0059(4) 0.0194(6) -0.0054(6) C14_1 0.0194(7) 0.0200(8) 0.0165(6) 0.0003(5) 0.0078(6) 0.0002(6) C15_1 0.0202(7) 0.0174(7) 0.0177(6) 0.0012(5) 0.0070(5) -0.0010(6) F15_1 0.0428(6) 0.0176(5) 0.0231(5) 0.0010(4) 0.0134(5) -0.0069(5) C16_1 0.0205(7) 0.0153(7) 0.0181(6) -0.0020(5) 0.0066(5) -0.0012(6) F16_1 0.0378(6) 0.0167(5) 0.0220(4) -0.0046(4) 0.0124(4) -0.0047(4) N21_1 0.0202(6) 0.0205(7) 0.0181(6) 0.0038(5) 0.0077(5) 0.0001(5) C22_1 0.0183(7) 0.0219(8) 0.0196(7) 0.0025(6) 0.0072(6) -0.0012(6) N22_1 0.0347(8) 0.0204(7) 0.0238(7) 0.0039(6) 0.0108(6) 0.0014(6) C23_1 0.0292(9) 0.0290(9) 0.0194(7) 0.0061(7) 0.0085(6) -0.0020(7) N24_1 0.0355(9) 0.0352(9) 0.0186(6) 0.0020(6) 0.0098(6) -0.0015(7) C25_1 0.0341(9) 0.0278(10) 0.0242(8) -0.0020(7) 0.0108(7) -0.0018(8) C26_1 0.0242(8) 0.0212(8) 0.0246(7) 0.0021(6) 0.0094(6) -0.0009(6) I2_2 0.01379(5) 0.02373(6) 0.01963(5) -0.00033(4) 0.00554(4) -0.00035(3) C11_2 0.0150(6) 0.0190(7) 0.0195(6) 0.0009(6) 0.0071(5) 0.0000(6) C17_2 0.0151(6) 0.0217(8) 0.0227(7) 0.0018(6) 0.0082(6) 0.0012(6) O11_2 0.0200(6) 0.0195(6) 0.0589(9) 0.0005(6) 0.0184(6) -0.0010(5) O12_2 0.0225(6) 0.0205(7) 0.0702(11) 0.0123(7) 0.0232(7) 0.0048(5) C12_2 0.0181(7) 0.0184(8) 0.0259(7) -0.0025(6) 0.0077(6) 0.0016(6) F12_2 0.0231(5) 0.0200(5) 0.0534(7) -0.0111(5) 0.0119(5) 0.0003(4) C13_2 0.0177(7) 0.0182(7) 0.0258(7) -0.0021(6) 0.0063(6) -0.0020(6) F13_2 0.0202(5) 0.0209(6) 0.0548(7) -0.0082(5) 0.0096(5) -0.0063(4) C14_2 0.0153(7) 0.0201(8) 0.0198(7) -0.0002(6) 0.0066(6) -0.0008(6) C15_2 0.0184(7) 0.0176(7) 0.0314(8) -0.0026(6) 0.0104(6) 0.0013(6) F15_2 0.0237(5) 0.0203(6) 0.0674(8) -0.0115(6) 0.0188(6) 0.0008(4) C16_2 0.0191(7) 0.0153(7) 0.0307(8) -0.0019(6) 0.0094(6) -0.0022(6) F16_2 0.0224(5) 0.0184(5) 0.0707(9) -0.0084(6) 0.0202(5) -0.0054(4) N21_2 0.0175(6) 0.0178(7) 0.0236(6) -0.0012(5) 0.0088(5) 0.0017(5) C22_2 0.0184(7) 0.0178(7) 0.0190(6) -0.0009(6) 0.0067(5) 0.0015(6) N22_2 0.0215(7) 0.0185(7) 0.0367(8) -0.0005(6) 0.0128(6) 0.0001(6) C23_2 0.0185(7) 0.0227(8) 0.0247(7) -0.0010(6) 0.0064(6) 0.0041(6) N24_2 0.0177(6) 0.0272(8) 0.0266(7) -0.0032(6) 0.0065(6) 0.0010(6) C25_2 0.0215(8) 0.0218(8) 0.0299(8) -0.0012(7) 0.0096(6) -0.0023(6) C26_2 0.0219(7) 0.0163(7) 0.0277(8) -0.0004(6) 0.0101(6) 0.0011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1_1 C14_1 2.0842(17) . ? I1_1 N24_1 2.9014(16) 1_554 ? C11_1 C16_1 1.393(2) . ? C11_1 C12_1 1.399(2) . ? C11_1 C17_1 1.520(2) . ? C17_1 O12_1 1.242(2) . ? C17_1 O11_1 1.262(2) . ? C12_1 F12_1 1.334(2) . ? C12_1 C13_1 1.386(2) . ? C13_1 F13_1 1.346(2) . ? C13_1 C14_1 1.383(3) . ? C14_1 C15_1 1.380(2) . ? C15_1 F15_1 1.342(2) . ? C15_1 C16_1 1.385(2) . ? C16_1 F16_1 1.3409(19) . ? N21_1 C22_1 1.345(2) . ? N21_1 C26_1 1.359(2) . ? N21_1 H21_1 0.91(2) . ? C22_1 N22_1 1.315(3) . ? C22_1 C23_1 1.435(2) . ? N22_1 H22A_1 0.91(3) . ? N22_1 H22B_1 0.89(3) . ? C23_1 N24_1 1.298(3) . ? C23_1 H23_1 0.9500 . ? N24_1 C25_1 1.366(3) . ? C25_1 C26_1 1.366(3) . ? C25_1 H25_1 0.9500 . ? C26_1 H26_1 0.9500 . ? I2_2 C14_2 2.0814(17) . ? I2_2 N24_2 2.8622(17) 1_455 ? C11_2 C12_2 1.392(2) . ? C11_2 C16_2 1.392(3) . ? C11_2 C17_2 1.524(2) . ? C17_2 O12_2 1.242(2) . ? C17_2 O11_2 1.250(2) . ? C12_2 F12_2 1.340(2) . ? C12_2 C13_2 1.388(2) . ? C13_2 F13_2 1.341(2) . ? C13_2 C14_2 1.385(3) . ? C14_2 C15_2 1.386(2) . ? C15_2 F15_2 1.334(2) . ? C15_2 C16_2 1.380(2) . ? C16_2 F16_2 1.340(2) . ? N21_2 C22_2 1.349(2) . ? N21_2 C26_2 1.357(2) . ? N21_2 H21_2 0.90(3) . ? C22_2 N22_2 1.316(2) . ? C22_2 C23_2 1.427(2) . ? N22_2 H22A_2 0.84(3) . ? N22_2 H22B_2 0.94(3) . ? C23_2 N24_2 1.303(3) . ? C23_2 H23_2 0.9500 . ? N24_2 C25_2 1.358(3) . ? C25_2 C26_2 1.364(3) . ? C25_2 H25_2 0.9500 . ? C26_2 H26_2 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 C14_1 I1_1 N24_1 174.66(6) . 1_554 ? C16_1 C11_1 C12_1 115.94(16) . . ? C16_1 C11_1 C17_1 122.90(15) . . ? C12_1 C11_1 C17_1 121.15(15) . . ? O12_1 C17_1 O11_1 126.36(17) . . ? O12_1 C17_1 C11_1 116.11(16) . . ? O11_1 C17_1 C11_1 117.52(15) . . ? F12_1 C12_1 C13_1 117.19(16) . . ? F12_1 C12_1 C11_1 121.07(16) . . ? C13_1 C12_1 C11_1 121.71(17) . . ? F13_1 C13_1 C14_1 120.26(15) . . ? F13_1 C13_1 C12_1 118.09(16) . . ? C14_1 C13_1 C12_1 121.64(16) . . ? C15_1 C14_1 C13_1 117.03(16) . . ? C15_1 C14_1 I1_1 120.99(13) . . ? C13_1 C14_1 I1_1 121.97(13) . . ? F15_1 C15_1 C14_1 119.95(15) . . ? F15_1 C15_1 C16_1 118.26(15) . . ? C14_1 C15_1 C16_1 121.78(16) . . ? F16_1 C16_1 C15_1 117.33(15) . . ? F16_1 C16_1 C11_1 120.70(14) . . ? C15_1 C16_1 C11_1 121.90(16) . . ? C22_1 N21_1 C26_1 121.49(15) . . ? C22_1 N21_1 H21_1 118.7(17) . . ? C26_1 N21_1 H21_1 119.8(17) . . ? N22_1 C22_1 N21_1 120.47(16) . . ? N22_1 C22_1 C23_1 123.08(18) . . ? N21_1 C22_1 C23_1 116.45(17) . . ? C22_1 N22_1 H22A_1 121.5(19) . . ? C22_1 N22_1 H22B_1 117.8(17) . . ? H22A_1 N22_1 H22B_1 118(3) . . ? N24_1 C23_1 C22_1 122.58(19) . . ? N24_1 C23_1 H23_1 118.7 . . ? C22_1 C23_1 H23_1 118.7 . . ? C23_1 N24_1 C25_1 119.10(17) . . ? N24_1 C25_1 C26_1 120.82(19) . . ? N24_1 C25_1 H25_1 119.6 . . ? C26_1 C25_1 H25_1 119.6 . . ? N21_1 C26_1 C25_1 119.53(18) . . ? N21_1 C26_1 H26_1 120.2 . . ? C25_1 C26_1 H26_1 120.2 . . ? C14_2 I2_2 N24_2 176.17(6) . 1_455 ? C12_2 C11_2 C16_2 115.77(15) . . ? C12_2 C11_2 C17_2 121.88(16) . . ? C16_2 C11_2 C17_2 122.34(16) . . ? O12_2 C17_2 O11_2 125.16(17) . . ? O12_2 C17_2 C11_2 116.95(16) . . ? O11_2 C17_2 C11_2 117.89(16) . . ? F12_2 C12_2 C13_2 116.36(16) . . ? F12_2 C12_2 C11_2 121.57(15) . . ? C13_2 C12_2 C11_2 122.06(17) . . ? F13_2 C13_2 C14_2 120.70(15) . . ? F13_2 C13_2 C12_2 117.81(16) . . ? C14_2 C13_2 C12_2 121.49(16) . . ? C13_2 C14_2 C15_2 116.75(16) . . ? C13_2 C14_2 I2_2 122.87(13) . . ? C15_2 C14_2 I2_2 120.33(13) . . ? F15_2 C15_2 C16_2 118.32(16) . . ? F15_2 C15_2 C14_2 119.94(16) . . ? C16_2 C15_2 C14_2 121.73(17) . . ? F16_2 C16_2 C15_2 116.25(16) . . ? F16_2 C16_2 C11_2 121.51(16) . . ? C15_2 C16_2 C11_2 122.19(16) . . ? C22_2 N21_2 C26_2 120.87(16) . . ? C22_2 N21_2 H21_2 116.5(17) . . ? C26_2 N21_2 H21_2 122.6(17) . . ? N22_2 C22_2 N21_2 120.80(16) . . ? N22_2 C22_2 C23_2 122.63(17) . . ? N21_2 C22_2 C23_2 116.57(16) . . ? C22_2 N22_2 H22A_2 119(2) . . ? C22_2 N22_2 H22B_2 119.6(16) . . ? H22A_2 N22_2 H22B_2 120(3) . . ? N24_2 C23_2 C22_2 122.62(17) . . ? N24_2 C23_2 H23_2 118.7 . . ? C22_2 C23_2 H23_2 118.7 . . ? C23_2 N24_2 C25_2 119.28(17) . . ? N24_2 C25_2 C26_2 120.43(18) . . ? N24_2 C25_2 H25_2 119.8 . . ? C26_2 C25_2 H25_2 119.8 . . ? N21_2 C26_2 C25_2 120.22(17) . . ? N21_2 C26_2 H26_2 119.9 . . ? C25_2 C26_2 H26_2 119.9 . . ? 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 C16_1 C11_1 C17_1 O12_1 -149.95(18) . . . . ? C12_1 C11_1 C17_1 O12_1 28.4(3) . . . . ? C16_1 C11_1 C17_1 O11_1 29.7(3) . . . . ? C12_1 C11_1 C17_1 O11_1 -151.99(18) . . . . ? C16_1 C11_1 C12_1 F12_1 -177.04(17) . . . . ? C17_1 C11_1 C12_1 F12_1 4.5(3) . . . . ? C16_1 C11_1 C12_1 C13_1 0.8(3) . . . . ? C17_1 C11_1 C12_1 C13_1 -177.70(17) . . . . ? F12_1 C12_1 C13_1 F13_1 -1.7(3) . . . . ? C11_1 C12_1 C13_1 F13_1 -179.56(17) . . . . ? F12_1 C12_1 C13_1 C14_1 177.42(18) . . . . ? C11_1 C12_1 C13_1 C14_1 -0.5(3) . . . . ? F13_1 C13_1 C14_1 C15_1 179.13(16) . . . . ? C12_1 C13_1 C14_1 C15_1 0.1(3) . . . . ? F13_1 C13_1 C14_1 I1_1 0.6(3) . . . . ? C12_1 C13_1 C14_1 I1_1 -178.45(14) . . . . ? N24_1 I1_1 C14_1 C15_1 -59.2(7) 1_554 . . . ? N24_1 I1_1 C14_1 C13_1 119.2(6) 1_554 . . . ? C13_1 C14_1 C15_1 F15_1 179.61(16) . . . . ? I1_1 C14_1 C15_1 F15_1 -1.9(2) . . . . ? C13_1 C14_1 C15_1 C16_1 0.0(3) . . . . ? I1_1 C14_1 C15_1 C16_1 178.53(13) . . . . ? F15_1 C15_1 C16_1 F16_1 -2.2(2) . . . . ? C14_1 C15_1 C16_1 F16_1 177.37(15) . . . . ? F15_1 C15_1 C16_1 C11_1 -179.27(15) . . . . ? C14_1 C15_1 C16_1 C11_1 0.3(3) . . . . ? C12_1 C11_1 C16_1 F16_1 -177.63(16) . . . . ? C17_1 C11_1 C16_1 F16_1 0.8(3) . . . . ? C12_1 C11_1 C16_1 C15_1 -0.7(3) . . . . ? C17_1 C11_1 C16_1 C15_1 177.73(16) . . . . ? C26_1 N21_1 C22_1 N22_1 -179.16(17) . . . . ? C26_1 N21_1 C22_1 C23_1 1.2(2) . . . . ? N22_1 C22_1 C23_1 N24_1 178.35(19) . . . . ? N21_1 C22_1 C23_1 N24_1 -2.0(3) . . . . ? C22_1 C23_1 N24_1 C25_1 1.6(3) . . . . ? C23_1 N24_1 C25_1 C26_1 -0.4(3) . . . . ? C22_1 N21_1 C26_1 C25_1 -0.1(3) . . . . ? N24_1 C25_1 C26_1 N21_1 -0.4(3) . . . . ? C12_2 C11_2 C17_2 O12_2 -19.5(3) . . . . ? C16_2 C11_2 C17_2 O12_2 159.32(18) . . . . ? C12_2 C11_2 C17_2 O11_2 160.77(18) . . . . ? C16_2 C11_2 C17_2 O11_2 -20.4(3) . . . . ? C16_2 C11_2 C12_2 F12_2 178.15(16) . . . . ? C17_2 C11_2 C12_2 F12_2 -2.9(3) . . . . ? C16_2 C11_2 C12_2 C13_2 -0.7(3) . . . . ? C17_2 C11_2 C12_2 C13_2 178.21(16) . . . . ? F12_2 C12_2 C13_2 F13_2 1.0(2) . . . . ? C11_2 C12_2 C13_2 F13_2 179.94(16) . . . . ? F12_2 C12_2 C13_2 C14_2 -178.44(16) . . . . ? C11_2 C12_2 C13_2 C14_2 0.5(3) . . . . ? F13_2 C13_2 C14_2 C15_2 -179.45(17) . . . . ? C12_2 C13_2 C14_2 C15_2 0.0(3) . . . . ? F13_2 C13_2 C14_2 I2_2 3.1(2) . . . . ? C12_2 C13_2 C14_2 I2_2 -177.49(13) . . . . ? N24_2 I2_2 C14_2 C13_2 117.1(9) 1_455 . . . ? N24_2 I2_2 C14_2 C15_2 -60.3(10) 1_455 . . . ? C13_2 C14_2 C15_2 F15_2 -179.33(17) . . . . ? I2_2 C14_2 C15_2 F15_2 -1.8(2) . . . . ? C13_2 C14_2 C15_2 C16_2 -0.2(3) . . . . ? I2_2 C14_2 C15_2 C16_2 177.36(14) . . . . ? F15_2 C15_2 C16_2 F16_2 1.6(3) . . . . ? C14_2 C15_2 C16_2 F16_2 -177.59(17) . . . . ? F15_2 C15_2 C16_2 C11_2 179.08(17) . . . . ? C14_2 C15_2 C16_2 C11_2 -0.1(3) . . . . ? C12_2 C11_2 C16_2 F16_2 177.90(17) . . . . ? C17_2 C11_2 C16_2 F16_2 -1.0(3) . . . . ? C12_2 C11_2 C16_2 C15_2 0.5(3) . . . . ? C17_2 C11_2 C16_2 C15_2 -178.40(17) . . . . ? C26_2 N21_2 C22_2 N22_2 179.11(17) . . . . ? C26_2 N21_2 C22_2 C23_2 -0.4(2) . . . . ? N22_2 C22_2 C23_2 N24_2 -178.58(17) . . . . ? N21_2 C22_2 C23_2 N24_2 0.9(3) . . . . ? C22_2 C23_2 N24_2 C25_2 -0.7(3) . . . . ? C23_2 N24_2 C25_2 C26_2 0.0(3) . . . . ? C22_2 N21_2 C26_2 C25_2 -0.2(3) . . . . ? N24_2 C25_2 C26_2 N21_2 0.5(3) . . . . ? 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 N21_1 H21_1 O11_1 0.91(2) 1.77(2) 2.6800(19) 177(2) . N21_2 H21_2 O11_2 0.90(3) 1.75(3) 2.636(2) 168(3) . N22_1 H22A_1 O12_1 0.91(3) 1.81(3) 2.710(2) 171(3) . N22_2 H22A_2 O12_2 0.84(3) 1.93(3) 2.754(2) 169(3) . N22_1 H22B_1 O12_2 0.89(3) 1.94(3) 2.779(2) 158(2) 3_666 N22_2 H22B_2 O11_1 0.94(3) 2.01(3) 2.893(2) 154(2) 1_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.319 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.115 #END data_pc0806m _database_code_depnum_ccdc_archive 'CCDC 809429' #TrackingRef '- allrevised.cif' #A2B1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; P59 2-aminopyrazine, 4-bromotetrafluorobenzoic acid ; _chemical_name_common 'P59 2-aminopyrazine, 4-bromotetrafluorobenzoic acid' _chemical_melting_point ? _chemical_formula_moiety ; C4 H5 N3, C7 H Br F4 O2 ; _chemical_formula_sum 'C11 H6 Br F4 N3 O2' _chemical_formula_weight 368.10 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' Br Br -0.2901 2.4595 '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 10.6236(4) _cell_length_b 10.6899(4) _cell_length_c 22.3295(9) _cell_angle_alpha 84.593(2) _cell_angle_beta 76.279(2) _cell_angle_gamma 90.002(2) _cell_volume 2451.87(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9986 _cell_measurement_theta_min 2.782 _cell_measurement_theta_max 33.064 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 3.413 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5485 _exptl_absorpt_correction_T_max 0.6285 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 54908 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 33.19 _reflns_number_total 54908 _reflns_number_gt 42573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 54908 _refine_ls_number_parameters 770 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.003 _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_1 Br 1.31168(4) 0.41284(3) 0.142908(13) 0.02210(6) Uani 1 1 d . . . C11_1 C 1.0251(3) 0.0976(2) 0.11459(11) 0.0165(5) Uani 1 1 d . . . C17_1 C 0.9215(3) 0.0045(2) 0.10832(11) 0.0169(5) Uani 1 1 d . . . O11_1 O 0.90974(18) -0.09775(16) 0.14147(8) 0.0248(4) Uani 1 1 d . . . O12_1 O 0.8565(2) 0.03916(17) 0.07087(8) 0.0231(4) Uani 1 1 d . . . C12_1 C 1.0749(3) 0.1940(2) 0.06919(11) 0.0202(5) Uani 1 1 d . . . F12_1 F 1.04168(16) 0.20297(14) 0.01466(7) 0.0301(4) Uani 1 1 d . . . C13_1 C 1.1593(3) 0.2868(2) 0.07634(12) 0.0215(6) Uani 1 1 d . . . F13_1 F 1.20106(18) 0.37729(15) 0.03033(8) 0.0323(4) Uani 1 1 d . . . C14_1 C 1.1997(3) 0.2859(2) 0.13145(12) 0.0172(5) Uani 1 1 d . . . C15_1 C 1.1551(3) 0.1896(3) 0.17650(11) 0.0192(5) Uani 1 1 d . . . F15_1 F 1.19456(19) 0.18295(15) 0.22950(7) 0.0285(4) Uani 1 1 d . . . C16_1 C 1.0733(3) 0.0974(2) 0.16868(11) 0.0187(6) Uani 1 1 d . . . F16_1 F 1.0334(2) 0.00716(15) 0.21569(6) 0.0271(4) Uani 1 1 d . . . N21_1 N 0.7038(3) -0.2353(2) 0.14539(10) 0.0164(5) Uani 1 1 d . . . H21_1 H 0.793(2) -0.173(2) 0.1415(11) 0.020 Uiso 1 1 d . . . C22_1 C 0.6356(3) -0.2226(2) 0.10109(11) 0.0165(5) Uani 1 1 d . . . N22_1 N 0.6724(3) -0.1351(2) 0.05434(9) 0.0224(5) Uani 1 1 d . . . H22A_1 H 0.7402 -0.0861 0.0523 0.027 Uiso 1 1 calc R . . H22B_1 H 0.6291 -0.1257 0.0252 0.027 Uiso 1 1 calc R . . C23_1 C 0.5277(3) -0.3061(2) 0.10975(12) 0.0267(6) Uani 1 1 d . . . H23_1 H 0.4812 -0.3025 0.0782 0.032 Uiso 1 1 calc R . . N24_1 N 0.4878(2) -0.3870(2) 0.15759(10) 0.0229(5) Uani 1 1 d . . . C25_1 C 0.5569(3) -0.3927(2) 0.20230(12) 0.0220(6) Uani 1 1 d . . . H25_1 H 0.5301 -0.4502 0.2383 0.026 Uiso 1 1 calc R . . C26_1 C 0.6614(3) -0.3188(2) 0.19611(12) 0.0219(6) Uani 1 1 d . . . H26_1 H 0.7073 -0.3247 0.2279 0.026 Uiso 1 1 calc R . . Br2_2 Br 0.82156(3) 0.40609(3) 0.131009(12) 0.01984(6) Uani 1 1 d . . . C11_2 C 0.5029(3) 0.1105(2) 0.11527(11) 0.0153(5) Uani 1 1 d . . . C17_2 C 0.4036(3) 0.0137(2) 0.10852(11) 0.0163(5) Uani 1 1 d . . . O11_2 O 0.3587(2) -0.06174(16) 0.15444(8) 0.0282(5) Uani 1 1 d . . . O12_2 O 0.3750(2) 0.01835(18) 0.05788(8) 0.0279(5) Uani 1 1 d . . . C12_2 C 0.5368(3) 0.2175(2) 0.07433(11) 0.0204(5) Uani 1 1 d . . . F12_2 F 0.47779(16) 0.24386(13) 0.02768(7) 0.0325(4) Uani 1 1 d . . . C13_2 C 0.6290(3) 0.3049(2) 0.07848(11) 0.0193(5) Uani 1 1 d . . . F13_2 F 0.65563(19) 0.40561(14) 0.03615(7) 0.0348(4) Uani 1 1 d . . . C14_2 C 0.6921(3) 0.2903(2) 0.12599(11) 0.0170(5) Uani 1 1 d . . . C15_2 C 0.6593(3) 0.1863(3) 0.16788(11) 0.0190(5) Uani 1 1 d . . . F15_2 F 0.72184(18) 0.16549(14) 0.21345(7) 0.0305(4) Uani 1 1 d . . . C16_2 C 0.5699(3) 0.0989(2) 0.16298(11) 0.0196(6) Uani 1 1 d . . . F16_2 F 0.5488(2) -0.00238(14) 0.20478(7) 0.0272(4) Uani 1 1 d . . . N21_2 N 0.1919(3) -0.2331(2) 0.14348(9) 0.0163(5) Uani 1 1 d . . . H21_2 H 0.269(2) -0.164(2) 0.1455(11) 0.020 Uiso 1 1 d . . . C22_2 C 0.1499(3) -0.2400(2) 0.09139(11) 0.0166(5) Uani 1 1 d . . . N22_2 N 0.1973(3) -0.1600(2) 0.04208(9) 0.0228(5) Uani 1 1 d . . . H22A_2 H 0.2558 -0.1028 0.0434 0.027 Uiso 1 1 calc R . . H22B_2 H 0.1702 -0.1641 0.0080 0.027 Uiso 1 1 calc R . . C23_2 C 0.0594(3) -0.3382(2) 0.09206(11) 0.0212(5) Uani 1 1 d . . . H23_2 H 0.0348 -0.3501 0.0547 0.025 Uiso 1 1 calc R . . N24_2 N 0.0081(3) -0.4135(2) 0.14194(10) 0.0221(5) Uani 1 1 d . . . C25_2 C 0.0492(3) -0.3995(2) 0.19430(12) 0.0209(6) Uani 1 1 d . . . H25_2 H 0.0138 -0.4532 0.2308 0.025 Uiso 1 1 calc R . . C26_2 C 0.1385(3) -0.3115(2) 0.19537(11) 0.0180(5) Uani 1 1 d . . . H26_2 H 0.1650 -0.3036 0.2326 0.022 Uiso 1 1 calc R . . Br3_3 Br 0.94735(3) 0.07936(2) 0.364627(18) 0.01889(5) Uani 1 1 d . . . C11_3 C 0.6358(3) 0.3958(2) 0.38912(11) 0.0150(5) Uani 1 1 d . . . C17_3 C 0.5254(3) 0.4887(2) 0.39588(11) 0.0152(5) Uani 1 1 d . . . O11_3 O 0.54707(16) 0.59167(15) 0.36194(8) 0.0224(4) Uani 1 1 d . . . O12_3 O 0.4198(2) 0.45500(15) 0.43300(8) 0.0199(4) Uani 1 1 d . . . C12_3 C 0.6398(2) 0.3021(2) 0.43665(10) 0.0151(4) Uani 1 1 d . . . F12_3 F 0.55311(12) 0.29811(13) 0.49203(6) 0.0232(3) Uani 1 1 d . . . C13_3 C 0.7323(3) 0.2106(2) 0.42989(11) 0.0176(5) Uani 1 1 d . . . F13_3 F 0.72779(16) 0.12309(13) 0.47786(7) 0.0281(4) Uani 1 1 d . . . C14_3 C 0.8253(3) 0.2062(2) 0.37561(11) 0.0156(5) Uani 1 1 d . . . C15_3 C 0.8245(3) 0.3004(2) 0.32828(11) 0.0178(5) Uani 1 1 d . . . F15_3 F 0.91360(15) 0.30203(14) 0.27419(6) 0.0261(4) Uani 1 1 d . . . C16_3 C 0.7302(3) 0.3926(2) 0.33534(10) 0.0157(5) Uani 1 1 d . . . F16_3 F 0.7382(2) 0.47680(13) 0.28658(6) 0.0269(4) Uani 1 1 d . . . N21_3 N 0.3419(3) 0.7306(2) 0.35770(10) 0.0165(5) Uani 1 1 d . . . H21_3 H 0.391(3) 0.700(3) 0.3600(13) 0.020 Uiso 1 1 d . . . C22_3 C 0.2332(3) 0.7170(2) 0.40203(11) 0.0152(5) Uani 1 1 d . . . N22_3 N 0.2212(2) 0.62917(18) 0.44899(9) 0.0199(4) Uani 1 1 d . . . H22A_3 H 0.2858 0.5788 0.4512 0.024 Uiso 1 1 calc R . . H22B_3 H 0.1487 0.6211 0.4780 0.024 Uiso 1 1 calc R . . C23_3 C 0.1308(2) 0.8027(2) 0.39540(10) 0.0188(5) Uani 1 1 d . . . H23_3 H 0.0528 0.7986 0.4269 0.023 Uiso 1 1 calc R . . N24_3 N 0.1423(2) 0.8856(2) 0.34741(10) 0.0213(5) Uani 1 1 d . . . C25_3 C 0.2536(3) 0.8922(2) 0.30255(11) 0.0193(6) Uani 1 1 d . . . H25_3 H 0.2613 0.9501 0.2668 0.023 Uiso 1 1 calc R . . C26_3 C 0.3557(3) 0.8163(2) 0.30793(11) 0.0171(5) Uani 1 1 d . . . H26_3 H 0.4349 0.8240 0.2771 0.020 Uiso 1 1 calc R . . Br4_4 Br 0.46039(3) 0.09791(2) 0.36164(2) 0.01972(5) Uani 1 1 d . . . C11_4 C 0.1273(3) 0.3928(2) 0.37939(11) 0.0145(5) Uani 1 1 d . . . C17_4 C 0.0196(3) 0.4877(2) 0.38706(11) 0.0161(5) Uani 1 1 d . . . O11_4 O 0.01845(18) 0.56346(16) 0.34038(7) 0.0265(4) Uani 1 1 d . . . O12_4 O -0.0589(2) 0.48772(16) 0.43845(8) 0.0250(5) Uani 1 1 d . . . C12_4 C 0.1196(3) 0.2854(2) 0.42131(11) 0.0173(5) Uani 1 1 d . . . F12_4 F 0.01373(15) 0.26028(13) 0.46802(6) 0.0267(3) Uani 1 1 d . . . C13_4 C 0.2170(3) 0.1985(2) 0.41571(11) 0.0194(5) Uani 1 1 d . . . F13_4 F 0.20063(17) 0.09768(13) 0.45747(7) 0.0294(4) Uani 1 1 d . . . C14_4 C 0.3263(3) 0.2134(2) 0.36875(11) 0.0164(5) Uani 1 1 d . . . C15_4 C 0.3365(3) 0.3189(2) 0.32687(11) 0.0149(5) Uani 1 1 d . . . F15_4 F 0.44300(15) 0.33942(14) 0.28003(7) 0.0273(4) Uani 1 1 d . . . C16_4 C 0.2374(3) 0.4066(2) 0.33203(11) 0.0150(5) Uani 1 1 d . . . F16_4 F 0.26122(18) 0.50784(13) 0.29074(7) 0.0236(4) Uani 1 1 d . . . N21_4 N -0.1626(3) 0.7324(2) 0.35192(10) 0.0162(5) Uani 1 1 d . . . H21_4 H -0.118(3) 0.688(2) 0.3499(12) 0.019 Uiso 1 1 d . . . C22_4 C -0.2528(3) 0.7419(2) 0.40398(12) 0.0171(5) Uani 1 1 d . . . N22_4 N -0.2548(2) 0.66488(19) 0.45447(9) 0.0215(5) Uani 1 1 d . . . H22A_4 H -0.1961 0.6066 0.4538 0.026 Uiso 1 1 calc R . . H22B_4 H -0.3149 0.6721 0.4886 0.026 Uiso 1 1 calc R . . C23_4 C -0.3471(3) 0.8386(2) 0.40182(12) 0.0213(5) Uani 1 1 d . . . H23_4 H -0.4122 0.8495 0.4382 0.026 Uiso 1 1 calc R . . N24_4 N -0.3456(2) 0.91145(19) 0.35142(10) 0.0221(5) Uani 1 1 d . . . C25_4 C -0.2524(3) 0.8970(2) 0.29948(12) 0.0192(5) Uani 1 1 d . . . H25_4 H -0.2519 0.9484 0.2623 0.023 Uiso 1 1 calc R . . C26_4 C -0.1585(3) 0.8087(2) 0.30008(12) 0.0181(5) Uani 1 1 d . . . H26B_4 H -0.0911 0.8017 0.2641 0.022 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_1 0.01996(13) 0.01785(10) 0.02955(13) -0.00420(9) -0.00726(11) -0.00344(10) C11_1 0.0170(12) 0.0149(10) 0.0172(10) -0.0012(8) -0.0032(9) -0.0005(9) C17_1 0.0154(12) 0.0165(11) 0.0187(11) -0.0065(9) -0.0023(10) -0.0013(10) O11_1 0.0255(10) 0.0210(8) 0.0292(9) 0.0061(7) -0.0120(7) -0.0109(7) O12_1 0.0264(9) 0.0224(8) 0.0231(8) 0.0034(6) -0.0134(8) -0.0088(7) C12_1 0.0235(13) 0.0205(11) 0.0195(10) -0.0001(8) -0.0114(10) -0.0011(9) F12_1 0.0361(9) 0.0334(8) 0.0233(7) 0.0104(6) -0.0170(6) -0.0157(7) C13_1 0.0240(13) 0.0147(10) 0.0256(12) 0.0061(9) -0.0085(10) -0.0056(9) F13_1 0.0385(10) 0.0274(8) 0.0298(7) 0.0146(6) -0.0127(7) -0.0174(7) C14_1 0.0138(12) 0.0164(11) 0.0221(11) -0.0039(9) -0.0047(10) -0.0021(10) C15_1 0.0182(13) 0.0241(12) 0.0157(10) -0.0037(9) -0.0038(10) 0.0022(10) F15_1 0.0374(9) 0.0322(8) 0.0195(7) 0.0005(6) -0.0150(7) -0.0117(6) C16_1 0.0231(14) 0.0165(11) 0.0135(10) 0.0025(8) -0.0002(10) 0.0007(10) F16_1 0.0344(9) 0.0293(7) 0.0161(6) 0.0081(5) -0.0069(6) -0.0142(7) N21_1 0.0176(11) 0.0137(9) 0.0187(10) 0.0018(8) -0.0072(9) -0.0018(8) C22_1 0.0165(12) 0.0160(10) 0.0169(10) -0.0017(8) -0.0037(9) -0.0025(9) N22_1 0.0239(11) 0.0258(10) 0.0172(9) 0.0048(8) -0.0068(8) -0.0117(9) C23_1 0.0305(15) 0.0290(13) 0.0237(12) 0.0015(10) -0.0140(11) -0.0116(11) N24_1 0.0224(11) 0.0248(10) 0.0198(10) 0.0031(8) -0.0037(9) -0.0061(9) C25_1 0.0280(16) 0.0166(11) 0.0198(11) 0.0019(9) -0.0037(11) 0.0000(11) C26_1 0.0305(15) 0.0174(11) 0.0205(11) 0.0023(9) -0.0128(11) 0.0022(10) Br2_2 0.01871(13) 0.01642(10) 0.02446(11) -0.00132(9) -0.00551(10) -0.00434(9) C11_2 0.0154(12) 0.0180(11) 0.0130(10) -0.0007(8) -0.0045(9) -0.0002(9) C17_2 0.0152(12) 0.0159(11) 0.0174(11) -0.0040(9) -0.0023(9) -0.0018(9) O11_2 0.0360(11) 0.0289(9) 0.0207(8) 0.0065(7) -0.0122(8) -0.0191(8) O12_2 0.0355(12) 0.0312(9) 0.0183(8) 0.0061(7) -0.0122(8) -0.0179(8) C12_2 0.0241(14) 0.0215(11) 0.0169(11) 0.0020(9) -0.0089(9) -0.0067(10) F12_2 0.0473(10) 0.0307(8) 0.0234(7) 0.0115(6) -0.0218(7) -0.0185(7) C13_2 0.0233(13) 0.0165(10) 0.0174(10) 0.0047(8) -0.0061(9) -0.0056(9) F13_2 0.0507(11) 0.0285(8) 0.0261(7) 0.0147(6) -0.0175(7) -0.0226(7) C14_2 0.0131(12) 0.0177(11) 0.0205(11) -0.0047(9) -0.0033(10) -0.0032(10) C15_2 0.0196(13) 0.0202(11) 0.0188(11) -0.0011(9) -0.0081(10) 0.0007(10) F15_2 0.0375(9) 0.0266(7) 0.0330(8) 0.0089(6) -0.0243(7) -0.0114(7) C16_2 0.0254(15) 0.0132(10) 0.0172(11) 0.0035(8) -0.0009(11) 0.0000(10) F16_2 0.0345(9) 0.0201(6) 0.0291(7) 0.0120(6) -0.0172(7) -0.0113(6) N21_2 0.0213(12) 0.0127(9) 0.0143(9) 0.0004(8) -0.0036(9) -0.0024(9) C22_2 0.0200(12) 0.0157(10) 0.0144(10) -0.0003(8) -0.0051(9) -0.0034(9) N22_2 0.0294(12) 0.0225(10) 0.0165(9) 0.0047(8) -0.0077(9) -0.0131(9) C23_2 0.0237(12) 0.0183(11) 0.0237(11) 0.0023(9) -0.0114(10) -0.0024(9) N24_2 0.0230(11) 0.0196(10) 0.0248(10) 0.0035(8) -0.0100(9) -0.0033(8) C25_2 0.0241(15) 0.0170(10) 0.0184(11) 0.0028(9) -0.0008(11) -0.0004(11) C26_2 0.0198(13) 0.0199(11) 0.0143(10) -0.0017(9) -0.0039(9) 0.0046(9) Br3_3 0.01759(12) 0.01646(11) 0.02334(10) -0.00306(9) -0.00586(10) 0.00769(9) C11_3 0.0129(11) 0.0130(10) 0.0201(11) -0.0008(8) -0.0065(9) 0.0026(8) C17_3 0.0172(12) 0.0159(10) 0.0133(10) 0.0006(8) -0.0059(9) 0.0025(9) O11_3 0.0175(8) 0.0192(8) 0.0283(8) 0.0047(7) -0.0037(7) 0.0036(6) O12_3 0.0161(8) 0.0197(7) 0.0230(8) 0.0019(6) -0.0039(7) 0.0054(7) C12_3 0.0126(10) 0.0185(10) 0.0124(9) 0.0020(8) -0.0011(8) 0.0025(8) F12_3 0.0194(6) 0.0293(7) 0.0157(6) 0.0067(5) 0.0031(5) 0.0076(5) C13_3 0.0186(11) 0.0147(10) 0.0199(11) 0.0040(8) -0.0077(9) 0.0044(8) F13_3 0.0305(8) 0.0236(7) 0.0245(7) 0.0122(6) -0.0007(6) 0.0097(6) C14_3 0.0182(13) 0.0116(10) 0.0176(11) 0.0006(8) -0.0061(10) 0.0037(9) C15_3 0.0178(13) 0.0194(11) 0.0142(10) -0.0013(8) -0.0003(9) 0.0086(10) F15_3 0.0257(8) 0.0344(8) 0.0138(6) 0.0000(6) 0.0030(5) 0.0125(6) C16_3 0.0117(11) 0.0183(10) 0.0163(10) 0.0029(8) -0.0038(9) 0.0054(9) F16_3 0.0318(9) 0.0270(7) 0.0165(6) 0.0098(5) 0.0005(6) 0.0127(7) N21_3 0.0133(11) 0.0174(10) 0.0178(9) 0.0011(8) -0.0025(9) 0.0039(9) C22_3 0.0180(11) 0.0143(10) 0.0142(10) -0.0010(8) -0.0058(9) 0.0050(9) N22_3 0.0168(9) 0.0219(9) 0.0176(9) 0.0067(7) -0.0006(8) 0.0067(8) C23_3 0.0150(10) 0.0249(11) 0.0159(10) 0.0006(9) -0.0032(8) 0.0089(9) N24_3 0.0238(11) 0.0218(10) 0.0170(9) 0.0017(8) -0.0036(8) 0.0119(9) C25_3 0.0205(14) 0.0189(11) 0.0155(10) 0.0048(9) -0.0009(10) 0.0031(10) C26_3 0.0164(11) 0.0163(10) 0.0167(10) 0.0016(9) -0.0018(9) 0.0038(9) Br4_4 0.01683(12) 0.01559(10) 0.02816(11) -0.00303(9) -0.00784(10) 0.00731(9) C11_4 0.0180(11) 0.0138(10) 0.0128(10) -0.0021(8) -0.0056(9) 0.0055(9) C17_4 0.0170(13) 0.0152(10) 0.0154(11) -0.0001(9) -0.0026(10) 0.0051(9) O11_4 0.0306(10) 0.0294(9) 0.0154(8) 0.0053(7) -0.0004(7) 0.0178(7) O12_4 0.0269(10) 0.0269(9) 0.0169(8) 0.0037(7) 0.0009(7) 0.0139(8) C12_4 0.0200(11) 0.0157(10) 0.0151(10) 0.0004(8) -0.0024(9) 0.0035(8) F12_4 0.0302(7) 0.0244(7) 0.0169(6) 0.0070(5) 0.0079(6) 0.0095(6) C13_4 0.0272(13) 0.0153(10) 0.0148(10) 0.0024(8) -0.0049(9) 0.0062(9) F13_4 0.0365(9) 0.0206(7) 0.0249(7) 0.0116(6) -0.0003(6) 0.0113(6) C14_4 0.0176(13) 0.0131(10) 0.0205(11) -0.0024(9) -0.0080(10) 0.0051(10) C15_4 0.0128(11) 0.0126(10) 0.0176(10) -0.0012(8) -0.0006(9) 0.0030(9) F15_4 0.0188(7) 0.0239(7) 0.0317(7) 0.0057(6) 0.0055(6) 0.0047(6) C16_4 0.0125(12) 0.0140(10) 0.0184(10) -0.0004(8) -0.0037(9) 0.0069(9) F16_4 0.0234(8) 0.0190(6) 0.0236(7) 0.0084(5) 0.0001(6) 0.0055(6) N21_4 0.0127(10) 0.0169(10) 0.0200(10) -0.0020(8) -0.0057(8) 0.0064(8) C22_4 0.0149(11) 0.0152(10) 0.0211(11) -0.0003(8) -0.0046(9) 0.0027(9) N22_4 0.0228(11) 0.0228(10) 0.0155(9) 0.0029(8) 0.0002(8) 0.0102(8) C23_4 0.0188(11) 0.0176(10) 0.0240(11) 0.0025(9) 0.0000(9) 0.0096(9) N24_4 0.0157(10) 0.0174(9) 0.0301(11) 0.0059(8) -0.0027(8) 0.0059(8) C25_4 0.0150(12) 0.0192(11) 0.0223(11) 0.0066(9) -0.0057(10) 0.0054(10) C26_4 0.0192(12) 0.0144(10) 0.0189(11) 0.0033(9) -0.0027(9) 0.0034(9) _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_1 C14_1 1.879(3) . ? Br1_1 N24_1 2.934(2) 1_665 ? C11_1 C12_1 1.386(4) . ? C11_1 C16_1 1.419(4) . ? C11_1 C17_1 1.523(4) . ? C17_1 O12_1 1.237(3) . ? C17_1 O11_1 1.250(3) . ? O11_1 H21_1 1.48(2) . ? C12_1 F12_1 1.341(3) . ? C12_1 C13_1 1.382(4) . ? C13_1 F13_1 1.336(3) . ? C13_1 C14_1 1.395(4) . ? C14_1 C15_1 1.370(4) . ? C15_1 F15_1 1.342(3) . ? C15_1 C16_1 1.364(4) . ? C16_1 F16_1 1.345(3) . ? N21_1 C22_1 1.355(4) . ? N21_1 C26_1 1.360(4) . ? N21_1 H21_1 1.14(2) . ? C22_1 N22_1 1.319(3) . ? C22_1 C23_1 1.418(4) . ? N22_1 H22A_1 0.8800 . ? N22_1 H22B_1 0.8800 . ? C23_1 N24_1 1.296(3) . ? C23_1 H23_1 0.9500 . ? N24_1 C25_1 1.370(4) . ? C25_1 C26_1 1.335(4) . ? C25_1 H25_1 0.9500 . ? C26_1 H26_1 0.9500 . ? Br2_2 C14_2 1.880(3) . ? Br2_2 N24_2 2.833(2) 1_665 ? C11_2 C12_2 1.385(3) . ? C11_2 C16_2 1.411(4) . ? C11_2 C17_2 1.521(4) . ? C17_2 O12_2 1.236(3) . ? C17_2 O11_2 1.241(3) . ? C12_2 F12_2 1.346(3) . ? C12_2 C13_2 1.378(4) . ? C13_2 F13_2 1.347(3) . ? C13_2 C14_2 1.381(4) . ? C14_2 C15_2 1.372(4) . ? C15_2 F15_2 1.344(3) . ? C15_2 C16_2 1.362(4) . ? C16_2 F16_2 1.343(3) . ? N21_2 C22_2 1.349(3) . ? N21_2 C26_2 1.368(4) . ? N21_2 H21_2 1.11(2) . ? C22_2 N22_2 1.325(3) . ? C22_2 C23_2 1.420(4) . ? N22_2 H22A_2 0.8800 . ? N22_2 H22B_2 0.8800 . ? C23_2 N24_2 1.315(3) . ? C23_2 H23_2 0.9500 . ? N24_2 C25_2 1.362(4) . ? C25_2 C26_2 1.342(4) . ? C25_2 H25_2 0.9500 . ? C26_2 H26_2 0.9500 . ? Br3_3 C14_3 1.869(3) . ? Br3_3 N24_3 2.916(2) 1_645 ? C11_3 C16_3 1.373(4) . ? C11_3 C12_3 1.397(3) . ? C11_3 C17_3 1.526(4) . ? C17_3 O12_3 1.256(3) . ? C17_3 O11_3 1.264(3) . ? C12_3 F12_3 1.353(2) . ? C12_3 C13_3 1.380(3) . ? C13_3 F13_3 1.346(3) . ? C13_3 C14_3 1.375(4) . ? C14_3 C15_3 1.391(4) . ? C15_3 F15_3 1.345(3) . ? C15_3 C16_3 1.398(4) . ? C16_3 F16_3 1.332(3) . ? N21_3 C22_3 1.329(4) . ? N21_3 C26_3 1.351(3) . ? N21_3 H21_3 0.62(3) . ? C22_3 N22_3 1.322(3) . ? C22_3 C23_3 1.447(3) . ? N22_3 H22A_3 0.8800 . ? N22_3 H22B_3 0.8800 . ? C23_3 N24_3 1.307(3) . ? C23_3 H23_3 0.9500 . ? N24_3 C25_3 1.353(4) . ? C25_3 C26_3 1.377(4) . ? C25_3 H25_3 0.9500 . ? C26_3 H26_3 0.9500 . ? Br4_4 C14_4 1.873(3) . ? Br4_4 N24_4 2.853(2) 1_645 ? C11_4 C16_4 1.375(4) . ? C11_4 C12_4 1.401(3) . ? C11_4 C17_4 1.519(4) . ? C17_4 O12_4 1.248(3) . ? C17_4 O11_4 1.261(3) . ? C12_4 F12_4 1.348(3) . ? C12_4 C13_4 1.382(4) . ? C13_4 F13_4 1.340(3) . ? C13_4 C14_4 1.365(4) . ? C14_4 C15_4 1.383(4) . ? C15_4 F15_4 1.348(3) . ? C15_4 C16_4 1.401(4) . ? C16_4 F16_4 1.337(3) . ? N21_4 C22_4 1.331(3) . ? N21_4 C26_4 1.344(3) . ? N21_4 H21_4 0.67(3) . ? C22_4 N22_4 1.328(3) . ? C22_4 C23_4 1.446(3) . ? N22_4 H22A_4 0.8800 . ? N22_4 H22B_4 0.8800 . ? C23_4 N24_4 1.303(3) . ? C23_4 H23_4 0.9500 . ? N24_4 C25_4 1.356(4) . ? C25_4 C26_4 1.375(4) . ? C25_4 H25_4 0.9500 . ? C26_4 H26B_4 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 C14_1 Br1_1 N24_1 178.62(9) . 1_665 ? C12_1 C11_1 C16_1 114.3(2) . . ? C12_1 C11_1 C17_1 122.6(2) . . ? C16_1 C11_1 C17_1 123.0(2) . . ? O12_1 C17_1 O11_1 126.6(3) . . ? O12_1 C17_1 C11_1 115.9(2) . . ? O11_1 C17_1 C11_1 117.5(2) . . ? C17_1 O11_1 H21_1 114.4(10) . . ? F12_1 C12_1 C13_1 115.6(2) . . ? F12_1 C12_1 C11_1 120.8(2) . . ? C13_1 C12_1 C11_1 123.6(2) . . ? F13_1 C13_1 C12_1 119.5(2) . . ? F13_1 C13_1 C14_1 120.5(2) . . ? C12_1 C13_1 C14_1 120.0(2) . . ? C15_1 C14_1 C13_1 117.7(3) . . ? C15_1 C14_1 Br1_1 121.5(2) . . ? C13_1 C14_1 Br1_1 120.8(2) . . ? F15_1 C15_1 C16_1 118.4(2) . . ? F15_1 C15_1 C14_1 119.7(3) . . ? C16_1 C15_1 C14_1 121.9(3) . . ? F16_1 C16_1 C15_1 117.8(2) . . ? F16_1 C16_1 C11_1 119.8(3) . . ? C15_1 C16_1 C11_1 122.4(2) . . ? C22_1 N21_1 C26_1 119.5(3) . . ? C22_1 N21_1 H21_1 120.4(13) . . ? C26_1 N21_1 H21_1 120.0(13) . . ? N22_1 C22_1 N21_1 118.9(3) . . ? N22_1 C22_1 C23_1 125.2(3) . . ? N21_1 C22_1 C23_1 115.9(2) . . ? C22_1 N22_1 H22A_1 120.0 . . ? C22_1 N22_1 H22B_1 120.0 . . ? H22A_1 N22_1 H22B_1 120.0 . . ? N24_1 C23_1 C22_1 124.8(2) . . ? N24_1 C23_1 H23_1 117.6 . . ? C22_1 C23_1 H23_1 117.6 . . ? C23_1 N24_1 C25_1 117.0(2) . . ? C26_1 C25_1 N24_1 121.1(2) . . ? C26_1 C25_1 H25_1 119.5 . . ? N24_1 C25_1 H25_1 119.5 . . ? C25_1 C26_1 N21_1 121.6(3) . . ? C25_1 C26_1 H26_1 119.2 . . ? N21_1 C26_1 H26_1 119.2 . . ? C14_2 Br2_2 N24_2 177.48(10) . 1_665 ? C12_2 C11_2 C16_2 114.1(2) . . ? C12_2 C11_2 C17_2 122.7(2) . . ? C16_2 C11_2 C17_2 123.3(2) . . ? O12_2 C17_2 O11_2 126.4(3) . . ? O12_2 C17_2 C11_2 116.7(2) . . ? O11_2 C17_2 C11_2 116.9(2) . . ? F12_2 C12_2 C13_2 115.3(2) . . ? F12_2 C12_2 C11_2 120.9(2) . . ? C13_2 C12_2 C11_2 123.8(2) . . ? F13_2 C13_2 C12_2 119.3(2) . . ? F13_2 C13_2 C14_2 120.3(2) . . ? C12_2 C13_2 C14_2 120.4(2) . . ? C15_2 C14_2 C13_2 117.3(3) . . ? C15_2 C14_2 Br2_2 121.8(2) . . ? C13_2 C14_2 Br2_2 120.9(2) . . ? F15_2 C15_2 C16_2 118.3(2) . . ? F15_2 C15_2 C14_2 119.4(3) . . ? C16_2 C15_2 C14_2 122.2(3) . . ? F16_2 C16_2 C15_2 117.6(3) . . ? F16_2 C16_2 C11_2 120.1(3) . . ? C15_2 C16_2 C11_2 122.3(2) . . ? C22_2 N21_2 C26_2 119.7(3) . . ? C22_2 N21_2 H21_2 121.5(13) . . ? C26_2 N21_2 H21_2 118.8(13) . . ? N22_2 C22_2 N21_2 119.7(2) . . ? N22_2 C22_2 C23_2 123.4(2) . . ? N21_2 C22_2 C23_2 116.9(2) . . ? C22_2 N22_2 H22A_2 120.0 . . ? C22_2 N22_2 H22B_2 120.0 . . ? H22A_2 N22_2 H22B_2 120.0 . . ? N24_2 C23_2 C22_2 123.1(2) . . ? N24_2 C23_2 H23_2 118.5 . . ? C22_2 C23_2 H23_2 118.5 . . ? C23_2 N24_2 C25_2 117.8(2) . . ? C26_2 C25_2 N24_2 121.4(2) . . ? C26_2 C25_2 H25_2 119.3 . . ? N24_2 C25_2 H25_2 119.3 . . ? C25_2 C26_2 N21_2 120.8(2) . . ? C25_2 C26_2 H26_2 119.6 . . ? N21_2 C26_2 H26_2 119.6 . . ? C14_3 Br3_3 N24_3 178.71(11) . 1_645 ? C16_3 C11_3 C12_3 116.2(2) . . ? C16_3 C11_3 C17_3 122.7(2) . . ? C12_3 C11_3 C17_3 120.9(2) . . ? O12_3 C17_3 O11_3 125.6(3) . . ? O12_3 C17_3 C11_3 117.5(2) . . ? O11_3 C17_3 C11_3 116.9(2) . . ? F12_3 C12_3 C13_3 116.84(19) . . ? F12_3 C12_3 C11_3 121.1(2) . . ? C13_3 C12_3 C11_3 122.1(2) . . ? F13_3 C13_3 C14_3 120.4(2) . . ? F13_3 C13_3 C12_3 118.0(2) . . ? C14_3 C13_3 C12_3 121.6(2) . . ? C13_3 C14_3 C15_3 117.1(2) . . ? C13_3 C14_3 Br3_3 122.15(18) . . ? C15_3 C14_3 Br3_3 120.8(2) . . ? F15_3 C15_3 C14_3 120.0(2) . . ? F15_3 C15_3 C16_3 119.0(2) . . ? C14_3 C15_3 C16_3 121.0(2) . . ? F16_3 C16_3 C11_3 122.4(2) . . ? F16_3 C16_3 C15_3 115.6(2) . . ? C11_3 C16_3 C15_3 122.0(2) . . ? C22_3 N21_3 C26_3 122.4(2) . . ? C22_3 N21_3 H21_3 121(3) . . ? C26_3 N21_3 H21_3 116(3) . . ? N22_3 C22_3 N21_3 120.9(2) . . ? N22_3 C22_3 C23_3 122.9(2) . . ? N21_3 C22_3 C23_3 116.2(2) . . ? C22_3 N22_3 H22A_3 120.0 . . ? C22_3 N22_3 H22B_3 120.0 . . ? H22A_3 N22_3 H22B_3 120.0 . . ? N24_3 C23_3 C22_3 122.1(2) . . ? N24_3 C23_3 H23_3 119.0 . . ? C22_3 C23_3 H23_3 119.0 . . ? C23_3 N24_3 C25_3 119.1(2) . . ? N24_3 C25_3 C26_3 121.0(2) . . ? N24_3 C25_3 H25_3 119.5 . . ? C26_3 C25_3 H25_3 119.5 . . ? N21_3 C26_3 C25_3 119.1(3) . . ? N21_3 C26_3 H26_3 120.5 . . ? C25_3 C26_3 H26_3 120.5 . . ? C14_4 Br4_4 N24_4 176.91(10) . 1_645 ? C16_4 C11_4 C12_4 116.1(2) . . ? C16_4 C11_4 C17_4 122.9(2) . . ? C12_4 C11_4 C17_4 121.0(2) . . ? O12_4 C17_4 O11_4 124.7(2) . . ? O12_4 C17_4 C11_4 118.9(2) . . ? O11_4 C17_4 C11_4 116.5(2) . . ? F12_4 C12_4 C13_4 116.9(2) . . ? F12_4 C12_4 C11_4 120.9(2) . . ? C13_4 C12_4 C11_4 122.1(2) . . ? F13_4 C13_4 C14_4 120.6(2) . . ? F13_4 C13_4 C12_4 118.0(2) . . ? C14_4 C13_4 C12_4 121.4(2) . . ? C13_4 C14_4 C15_4 117.7(3) . . ? C13_4 C14_4 Br4_4 121.73(19) . . ? C15_4 C14_4 Br4_4 120.6(2) . . ? F15_4 C15_4 C14_4 120.3(2) . . ? F15_4 C15_4 C16_4 118.6(2) . . ? C14_4 C15_4 C16_4 121.1(2) . . ? F16_4 C16_4 C11_4 122.6(2) . . ? F16_4 C16_4 C15_4 115.6(2) . . ? C11_4 C16_4 C15_4 121.7(2) . . ? C22_4 N21_4 C26_4 122.1(2) . . ? C22_4 N21_4 H21_4 122(2) . . ? C26_4 N21_4 H21_4 116(2) . . ? N22_4 C22_4 N21_4 120.8(2) . . ? N22_4 C22_4 C23_4 122.7(2) . . ? N21_4 C22_4 C23_4 116.4(2) . . ? C22_4 N22_4 H22A_4 120.0 . . ? C22_4 N22_4 H22B_4 120.0 . . ? H22A_4 N22_4 H22B_4 120.0 . . ? N24_4 C23_4 C22_4 121.9(2) . . ? N24_4 C23_4 H23_4 119.0 . . ? C22_4 C23_4 H23_4 119.0 . . ? C23_4 N24_4 C25_4 119.3(2) . . ? N24_4 C25_4 C26_4 120.6(2) . . ? N24_4 C25_4 H25_4 119.7 . . ? C26_4 C25_4 H25_4 119.7 . . ? N21_4 C26_4 C25_4 119.6(2) . . ? N21_4 C26_4 H26B_4 120.2 . . ? C25_4 C26_4 H26B_4 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12_1 C11_1 C17_1 O12_1 -20.9(4) . . . . ? C16_1 C11_1 C17_1 O12_1 155.4(3) . . . . ? C12_1 C11_1 C17_1 O11_1 159.7(3) . . . . ? C16_1 C11_1 C17_1 O11_1 -24.0(4) . . . . ? C16_1 C11_1 C12_1 F12_1 177.5(2) . . . . ? C17_1 C11_1 C12_1 F12_1 -5.9(4) . . . . ? C16_1 C11_1 C12_1 C13_1 -3.2(4) . . . . ? C17_1 C11_1 C12_1 C13_1 173.4(3) . . . . ? F12_1 C12_1 C13_1 F13_1 0.3(4) . . . . ? C11_1 C12_1 C13_1 F13_1 -179.0(3) . . . . ? F12_1 C12_1 C13_1 C14_1 179.9(3) . . . . ? C11_1 C12_1 C13_1 C14_1 0.6(4) . . . . ? F13_1 C13_1 C14_1 C15_1 -179.0(3) . . . . ? C12_1 C13_1 C14_1 C15_1 1.4(4) . . . . ? F13_1 C13_1 C14_1 Br1_1 0.9(4) . . . . ? C12_1 C13_1 C14_1 Br1_1 -178.8(2) . . . . ? N24_1 Br1_1 C14_1 C15_1 167(4) 1_665 . . . ? N24_1 Br1_1 C14_1 C13_1 -13(4) 1_665 . . . ? C13_1 C14_1 C15_1 F15_1 178.0(3) . . . . ? Br1_1 C14_1 C15_1 F15_1 -1.9(4) . . . . ? C13_1 C14_1 C15_1 C16_1 -0.5(4) . . . . ? Br1_1 C14_1 C15_1 C16_1 179.7(2) . . . . ? F15_1 C15_1 C16_1 F16_1 2.2(4) . . . . ? C14_1 C15_1 C16_1 F16_1 -179.3(3) . . . . ? F15_1 C15_1 C16_1 C11_1 179.1(3) . . . . ? C14_1 C15_1 C16_1 C11_1 -2.4(5) . . . . ? C12_1 C11_1 C16_1 F16_1 -179.1(2) . . . . ? C17_1 C11_1 C16_1 F16_1 4.4(4) . . . . ? C12_1 C11_1 C16_1 C15_1 4.1(4) . . . . ? C17_1 C11_1 C16_1 C15_1 -172.5(3) . . . . ? C26_1 N21_1 C22_1 N22_1 175.2(2) . . . . ? C26_1 N21_1 C22_1 C23_1 -4.2(4) . . . . ? N22_1 C22_1 C23_1 N24_1 -175.8(3) . . . . ? N21_1 C22_1 C23_1 N24_1 3.5(4) . . . . ? C22_1 C23_1 N24_1 C25_1 -1.0(4) . . . . ? C23_1 N24_1 C25_1 C26_1 -0.7(4) . . . . ? N24_1 C25_1 C26_1 N21_1 -0.2(4) . . . . ? C22_1 N21_1 C26_1 C25_1 2.8(4) . . . . ? C12_2 C11_2 C17_2 O12_2 15.8(4) . . . . ? C16_2 C11_2 C17_2 O12_2 -163.3(3) . . . . ? C12_2 C11_2 C17_2 O11_2 -163.8(3) . . . . ? C16_2 C11_2 C17_2 O11_2 17.1(4) . . . . ? C16_2 C11_2 C12_2 F12_2 -177.6(2) . . . . ? C17_2 C11_2 C12_2 F12_2 3.3(4) . . . . ? C16_2 C11_2 C12_2 C13_2 1.0(4) . . . . ? C17_2 C11_2 C12_2 C13_2 -178.2(2) . . . . ? F12_2 C12_2 C13_2 F13_2 -1.7(4) . . . . ? C11_2 C12_2 C13_2 F13_2 179.7(2) . . . . ? F12_2 C12_2 C13_2 C14_2 177.4(2) . . . . ? C11_2 C12_2 C13_2 C14_2 -1.2(4) . . . . ? F13_2 C13_2 C14_2 C15_2 179.2(3) . . . . ? C12_2 C13_2 C14_2 C15_2 0.2(4) . . . . ? F13_2 C13_2 C14_2 Br2_2 -2.7(4) . . . . ? C12_2 C13_2 C14_2 Br2_2 178.2(2) . . . . ? N24_2 Br2_2 C14_2 C15_2 -90(2) 1_665 . . . ? N24_2 Br2_2 C14_2 C13_2 92(2) 1_665 . . . ? C13_2 C14_2 C15_2 F15_2 177.3(2) . . . . ? Br2_2 C14_2 C15_2 F15_2 -0.7(4) . . . . ? C13_2 C14_2 C15_2 C16_2 1.1(4) . . . . ? Br2_2 C14_2 C15_2 C16_2 -176.9(2) . . . . ? F15_2 C15_2 C16_2 F16_2 0.8(4) . . . . ? C14_2 C15_2 C16_2 F16_2 177.1(3) . . . . ? F15_2 C15_2 C16_2 C11_2 -177.6(2) . . . . ? C14_2 C15_2 C16_2 C11_2 -1.4(4) . . . . ? C12_2 C11_2 C16_2 F16_2 -178.1(2) . . . . ? C17_2 C11_2 C16_2 F16_2 1.0(4) . . . . ? C12_2 C11_2 C16_2 C15_2 0.3(4) . . . . ? C17_2 C11_2 C16_2 C15_2 179.5(3) . . . . ? C26_2 N21_2 C22_2 N22_2 176.8(3) . . . . ? C26_2 N21_2 C22_2 C23_2 -5.8(4) . . . . ? N22_2 C22_2 C23_2 N24_2 -176.6(3) . . . . ? N21_2 C22_2 C23_2 N24_2 6.0(4) . . . . ? C22_2 C23_2 N24_2 C25_2 -3.3(4) . . . . ? C23_2 N24_2 C25_2 C26_2 0.4(4) . . . . ? N24_2 C25_2 C26_2 N21_2 -0.3(4) . . . . ? C22_2 N21_2 C26_2 C25_2 3.2(4) . . . . ? C16_3 C11_3 C17_3 O12_3 150.8(3) . . . . ? C12_3 C11_3 C17_3 O12_3 -24.2(3) . . . . ? C16_3 C11_3 C17_3 O11_3 -26.9(4) . . . . ? C12_3 C11_3 C17_3 O11_3 158.1(2) . . . . ? C16_3 C11_3 C12_3 F12_3 178.6(2) . . . . ? C17_3 C11_3 C12_3 F12_3 -6.2(4) . . . . ? C16_3 C11_3 C12_3 C13_3 -0.7(4) . . . . ? C17_3 C11_3 C12_3 C13_3 174.6(2) . . . . ? F12_3 C12_3 C13_3 F13_3 1.5(3) . . . . ? C11_3 C12_3 C13_3 F13_3 -179.2(2) . . . . ? F12_3 C12_3 C13_3 C14_3 -179.7(2) . . . . ? C11_3 C12_3 C13_3 C14_3 -0.4(4) . . . . ? F13_3 C13_3 C14_3 C15_3 -179.5(2) . . . . ? C12_3 C13_3 C14_3 C15_3 1.8(4) . . . . ? F13_3 C13_3 C14_3 Br3_3 1.1(4) . . . . ? C12_3 C13_3 C14_3 Br3_3 -177.6(2) . . . . ? N24_3 Br3_3 C14_3 C13_3 -112(4) 1_645 . . . ? N24_3 Br3_3 C14_3 C15_3 68(4) 1_645 . . . ? C13_3 C14_3 C15_3 F15_3 179.5(2) . . . . ? Br3_3 C14_3 C15_3 F15_3 -1.1(4) . . . . ? C13_3 C14_3 C15_3 C16_3 -2.0(4) . . . . ? Br3_3 C14_3 C15_3 C16_3 177.4(2) . . . . ? C12_3 C11_3 C16_3 F16_3 -179.5(2) . . . . ? C17_3 C11_3 C16_3 F16_3 5.3(4) . . . . ? C12_3 C11_3 C16_3 C15_3 0.5(4) . . . . ? C17_3 C11_3 C16_3 C15_3 -174.7(3) . . . . ? F15_3 C15_3 C16_3 F16_3 -0.6(4) . . . . ? C14_3 C15_3 C16_3 F16_3 -179.1(3) . . . . ? F15_3 C15_3 C16_3 C11_3 179.4(3) . . . . ? C14_3 C15_3 C16_3 C11_3 0.9(4) . . . . ? C26_3 N21_3 C22_3 N22_3 177.5(2) . . . . ? C26_3 N21_3 C22_3 C23_3 -2.3(4) . . . . ? N22_3 C22_3 C23_3 N24_3 -177.1(2) . . . . ? N21_3 C22_3 C23_3 N24_3 2.6(4) . . . . ? C22_3 C23_3 N24_3 C25_3 -0.3(4) . . . . ? C23_3 N24_3 C25_3 C26_3 -2.4(4) . . . . ? C22_3 N21_3 C26_3 C25_3 -0.3(4) . . . . ? N24_3 C25_3 C26_3 N21_3 2.7(4) . . . . ? C16_4 C11_4 C17_4 O12_4 -161.2(3) . . . . ? C12_4 C11_4 C17_4 O12_4 18.3(4) . . . . ? C16_4 C11_4 C17_4 O11_4 17.3(4) . . . . ? C12_4 C11_4 C17_4 O11_4 -163.2(2) . . . . ? C16_4 C11_4 C12_4 F12_4 -177.4(2) . . . . ? C17_4 C11_4 C12_4 F12_4 3.1(4) . . . . ? C16_4 C11_4 C12_4 C13_4 0.3(4) . . . . ? C17_4 C11_4 C12_4 C13_4 -179.2(2) . . . . ? F12_4 C12_4 C13_4 F13_4 -1.4(3) . . . . ? C11_4 C12_4 C13_4 F13_4 -179.1(2) . . . . ? F12_4 C12_4 C13_4 C14_4 177.9(2) . . . . ? C11_4 C12_4 C13_4 C14_4 0.1(4) . . . . ? F13_4 C13_4 C14_4 C15_4 179.4(2) . . . . ? C12_4 C13_4 C14_4 C15_4 0.1(4) . . . . ? F13_4 C13_4 C14_4 Br4_4 -2.1(4) . . . . ? C12_4 C13_4 C14_4 Br4_4 178.7(2) . . . . ? N24_4 Br4_4 C14_4 C13_4 51.0(17) 1_645 . . . ? N24_4 Br4_4 C14_4 C15_4 -130.5(16) 1_645 . . . ? C13_4 C14_4 C15_4 F15_4 179.1(2) . . . . ? Br4_4 C14_4 C15_4 F15_4 0.5(4) . . . . ? C13_4 C14_4 C15_4 C16_4 -0.8(4) . . . . ? Br4_4 C14_4 C15_4 C16_4 -179.4(2) . . . . ? C12_4 C11_4 C16_4 F16_4 -176.1(2) . . . . ? C17_4 C11_4 C16_4 F16_4 3.4(4) . . . . ? C12_4 C11_4 C16_4 C15_4 -0.9(4) . . . . ? C17_4 C11_4 C16_4 C15_4 178.6(2) . . . . ? F15_4 C15_4 C16_4 F16_4 -3.2(4) . . . . ? C14_4 C15_4 C16_4 F16_4 176.7(2) . . . . ? F15_4 C15_4 C16_4 C11_4 -178.7(2) . . . . ? C14_4 C15_4 C16_4 C11_4 1.3(4) . . . . ? C26_4 N21_4 C22_4 N22_4 179.8(3) . . . . ? C26_4 N21_4 C22_4 C23_4 0.4(4) . . . . ? N22_4 C22_4 C23_4 N24_4 -178.3(3) . . . . ? N21_4 C22_4 C23_4 N24_4 1.1(4) . . . . ? C22_4 C23_4 N24_4 C25_4 -0.5(4) . . . . ? C23_4 N24_4 C25_4 C26_4 -1.5(4) . . . . ? C22_4 N21_4 C26_4 C25_4 -2.3(4) . . . . ? N24_4 C25_4 C26_4 N21_4 3.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21_1 H21_1 O11_1 1.14(2) 1.48(2) 2.616(3) 175(2) . N21_2 H21_2 O11_2 1.11(2) 1.51(2) 2.617(3) 172(2) . N21_3 H21_3 O11_3 0.62(3) 2.03(3) 2.653(3) 175(3) . N21_4 H21_4 O11_4 0.67(3) 1.95(3) 2.623(3) 177(3) . N22_1 H22A_1 O12_1 0.88 1.96 2.812(3) 162.4 . N22_2 H22A_2 O12_2 0.88 1.91 2.787(3) 172.5 . N22_3 H22A_3 O12_3 0.88 1.94 2.795(3) 163.1 . N22_4 H22A_4 O12_4 0.88 1.92 2.797(3) 170.9 . N22_1 H22B_1 O12_2 0.88 2.10 2.846(3) 142.5 2_655 N22_2 H22B_2 O12_1 0.88 2.18 2.903(3) 138.9 2_655 N22_3 H22B_3 O12_4 0.88 2.12 2.864(3) 142.1 2_566 N22_4 H22B_4 O12_3 0.88 2.19 2.887(3) 136.2 2_566 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 33.19 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.188 _refine_diff_density_min -0.933 _refine_diff_density_rms 0.111 #END data_pc1006m _database_code_depnum_ccdc_archive 'CCDC 809430' #TrackingRef '- allrevised.cif' #A1B2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; PC-4-7b 2-amino-5-bromopyrazine, 4-I-F4-PhCOOH ; _chemical_name_common 'PC-4-7b 2-amino-5-bromopyrazine, 4-I-F4-PhCOOH' _chemical_melting_point ? _chemical_formula_moiety ; C4 H4 Br N3, C7 H F4 I O2 ; _chemical_formula_sum 'C11 H5 Br F4 I N3 O2' _chemical_formula_weight 493.99 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3341(10) _cell_length_b 14.1571(10) _cell_length_c 6.8919(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.564(3) _cell_angle_gamma 90.00 _cell_volume 1389.40(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9896 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 33.75 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 5.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3430 _exptl_absorpt_correction_T_max 0.5722 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24833 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 33.14 _reflns_number_total 5302 _reflns_number_gt 4470 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5302 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 I1 I -0.097383(10) 0.355672(11) 0.79433(2) 0.02052(5) Uani 1 1 d . . . Br1 Br 0.672532(17) -0.006422(15) 0.39862(4) 0.02069(6) Uani 1 1 d . . . N11 N 0.52484(12) 0.23988(12) 0.4358(3) 0.0148(3) Uani 1 1 d . . . C12 C 0.58985(15) 0.30529(15) 0.4097(3) 0.0151(4) Uani 1 1 d . . . N12 N 0.56471(15) 0.39685(13) 0.4112(3) 0.0205(4) Uani 1 1 d . . . H12A H 0.509(2) 0.403(2) 0.431(5) 0.025 Uiso 1 1 d . . . H12B H 0.600(2) 0.438(2) 0.394(4) 0.025 Uiso 1 1 d . . . C13 C 0.68180(15) 0.27627(15) 0.3776(3) 0.0163(4) Uani 1 1 d . . . H13 H 0.7276 0.3228 0.3582 0.020 Uiso 1 1 calc R . . N14 N 0.70501(13) 0.18613(13) 0.3743(3) 0.0168(3) Uani 1 1 d . . . C15 C 0.63890(15) 0.12224(14) 0.4025(3) 0.0149(4) Uani 1 1 d . . . C16 C 0.54946(15) 0.14830(14) 0.4327(3) 0.0153(4) Uani 1 1 d . . . H16 H 0.5044 0.1010 0.4517 0.018 Uiso 1 1 calc R . . C21 C 0.22880(15) 0.34256(14) 0.6313(3) 0.0142(4) Uani 1 1 d . . . C27 C 0.32724(15) 0.33903(14) 0.5804(3) 0.0145(4) Uani 1 1 d . . . O21 O 0.34970(12) 0.25676(11) 0.5124(3) 0.0212(3) Uani 1 1 d . . . H21 H 0.400(2) 0.259(2) 0.485(5) 0.025 Uiso 1 1 d . . . O22 O 0.38056(11) 0.40597(11) 0.6023(3) 0.0198(3) Uani 1 1 d . . . C22 C 0.18150(15) 0.42885(14) 0.6451(3) 0.0160(4) Uani 1 1 d . . . F22 F 0.22425(10) 0.51035(9) 0.6079(2) 0.0220(3) Uani 1 1 d . . . C23 C 0.09076(15) 0.43370(15) 0.6914(3) 0.0160(4) Uani 1 1 d . . . F23 F 0.05083(10) 0.51906(9) 0.6984(2) 0.0242(3) Uani 1 1 d . . . C24 C 0.04060(15) 0.35304(15) 0.7291(3) 0.0160(4) Uani 1 1 d . . . C25 C 0.08647(15) 0.26749(14) 0.7185(3) 0.0153(4) Uani 1 1 d . . . F25 F 0.04357(10) 0.18672(9) 0.7547(2) 0.0214(3) Uani 1 1 d . . . C26 C 0.17747(15) 0.26231(14) 0.6697(3) 0.0151(4) Uani 1 1 d . . . F26 F 0.21494(10) 0.17558(9) 0.6650(2) 0.0207(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 I1 0.01213(7) 0.02764(8) 0.02246(8) 0.00047(5) 0.00483(5) 0.00311(5) Br1 0.01992(11) 0.01410(10) 0.02877(13) 0.00007(8) 0.00592(9) 0.00380(7) N11 0.0123(8) 0.0146(7) 0.0178(8) -0.0006(6) 0.0035(6) 0.0018(6) C12 0.0142(9) 0.0171(9) 0.0143(9) -0.0002(7) 0.0032(7) 0.0003(7) N12 0.0190(9) 0.0135(8) 0.0296(11) 0.0002(7) 0.0058(8) -0.0002(7) C13 0.0138(9) 0.0159(9) 0.0196(10) -0.0003(7) 0.0039(8) -0.0015(7) N14 0.0130(8) 0.0175(8) 0.0205(9) -0.0008(7) 0.0048(7) 0.0003(6) C15 0.0147(9) 0.0140(8) 0.0167(10) -0.0002(7) 0.0041(7) 0.0014(7) C16 0.0133(9) 0.0148(9) 0.0183(10) -0.0004(7) 0.0039(7) -0.0013(7) C21 0.0122(9) 0.0143(9) 0.0161(9) -0.0003(7) 0.0023(7) 0.0011(7) C27 0.0110(8) 0.0155(9) 0.0168(10) 0.0009(7) 0.0015(7) 0.0018(7) O21 0.0131(7) 0.0183(7) 0.0336(10) -0.0060(6) 0.0080(7) 0.0006(6) O22 0.0148(7) 0.0163(7) 0.0292(9) 0.0004(6) 0.0066(6) -0.0008(6) C22 0.0138(9) 0.0139(8) 0.0204(10) 0.0013(7) 0.0023(8) 0.0007(7) F22 0.0191(7) 0.0117(6) 0.0358(8) 0.0032(5) 0.0061(6) -0.0003(5) C23 0.0145(9) 0.0141(9) 0.0195(10) -0.0006(7) 0.0028(8) 0.0042(7) F23 0.0211(7) 0.0160(6) 0.0365(8) -0.0006(5) 0.0076(6) 0.0072(5) C24 0.0116(9) 0.0200(9) 0.0168(10) 0.0002(7) 0.0029(7) 0.0027(7) C25 0.0137(9) 0.0136(8) 0.0189(10) 0.0022(7) 0.0028(7) -0.0022(7) F25 0.0174(6) 0.0172(6) 0.0299(8) 0.0024(5) 0.0042(6) -0.0047(5) C26 0.0131(9) 0.0130(8) 0.0193(10) 0.0005(7) 0.0027(7) 0.0025(7) F26 0.0196(6) 0.0099(5) 0.0333(8) 0.0008(5) 0.0059(6) 0.0031(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 I1 C24 2.078(2) . ? I1 N14 3.0057(19) 4_466 ? Br1 C15 1.885(2) . ? N11 C12 1.340(3) . ? N11 C16 1.345(3) . ? C12 N12 1.346(3) . ? C12 C13 1.422(3) . ? N12 H12A 0.83(3) . ? N12 H12B 0.79(3) . ? C13 N14 1.320(3) . ? C13 H13 0.9500 . ? N14 C15 1.340(3) . ? C15 C16 1.373(3) . ? C16 H16 0.9500 . ? C21 C26 1.395(3) . ? C21 C22 1.406(3) . ? C21 C27 1.493(3) . ? C27 O22 1.216(3) . ? C27 O21 1.309(3) . ? O21 H21 0.77(3) . ? C22 F22 1.345(2) . ? C22 C23 1.376(3) . ? C23 F23 1.340(2) . ? C23 C24 1.390(3) . ? C24 C25 1.384(3) . ? C25 F25 1.335(2) . ? C25 C26 1.386(3) . ? C26 F26 1.342(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 C24 I1 N14 167.50(7) . 4_466 ? C12 N11 C16 118.45(18) . . ? N11 C12 N12 118.3(2) . . ? N11 C12 C13 119.49(19) . . ? N12 C12 C13 122.2(2) . . ? C12 N12 H12A 111(2) . . ? C12 N12 H12B 122(2) . . ? H12A N12 H12B 127(3) . . ? N14 C13 C12 121.48(19) . . ? N14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 N14 C15 117.79(19) . . ? N14 C15 C16 121.93(19) . . ? N14 C15 Br1 117.63(16) . . ? C16 C15 Br1 120.44(16) . . ? N11 C16 C15 120.86(19) . . ? N11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C26 C21 C22 115.22(19) . . ? C26 C21 C27 123.38(18) . . ? C22 C21 C27 121.40(19) . . ? O22 C27 O21 124.1(2) . . ? O22 C27 C21 122.84(19) . . ? O21 C27 C21 113.05(18) . . ? C27 O21 H21 109(2) . . ? F22 C22 C23 117.70(18) . . ? F22 C22 C21 119.93(19) . . ? C23 C22 C21 122.3(2) . . ? F23 C23 C22 118.2(2) . . ? F23 C23 C24 120.1(2) . . ? C22 C23 C24 121.69(19) . . ? C25 C24 C23 116.8(2) . . ? C25 C24 I1 119.78(16) . . ? C23 C24 I1 123.46(15) . . ? F25 C25 C24 120.52(19) . . ? F25 C25 C26 117.81(18) . . ? C24 C25 C26 121.67(19) . . ? F26 C26 C25 116.39(18) . . ? F26 C26 C21 121.29(19) . . ? C25 C26 C21 122.30(19) . . ? 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 C16 N11 C12 N12 179.5(2) . . . . ? C16 N11 C12 C13 0.7(3) . . . . ? N11 C12 C13 N14 -0.5(3) . . . . ? N12 C12 C13 N14 -179.2(2) . . . . ? C12 C13 N14 C15 -0.1(3) . . . . ? C13 N14 C15 C16 0.5(3) . . . . ? C13 N14 C15 Br1 -179.77(16) . . . . ? C12 N11 C16 C15 -0.4(3) . . . . ? N14 C15 C16 N11 -0.2(3) . . . . ? Br1 C15 C16 N11 179.99(16) . . . . ? C26 C21 C27 O22 -158.0(2) . . . . ? C22 C21 C27 O22 21.6(3) . . . . ? C26 C21 C27 O21 21.4(3) . . . . ? C22 C21 C27 O21 -159.0(2) . . . . ? C26 C21 C22 F22 -178.96(19) . . . . ? C27 C21 C22 F22 1.5(3) . . . . ? C26 C21 C22 C23 -0.5(3) . . . . ? C27 C21 C22 C23 179.9(2) . . . . ? F22 C22 C23 F23 -0.6(3) . . . . ? C21 C22 C23 F23 -179.04(19) . . . . ? F22 C22 C23 C24 179.0(2) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? F23 C23 C24 C25 179.83(19) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? F23 C23 C24 I1 0.8(3) . . . . ? C22 C23 C24 I1 -178.75(17) . . . . ? N14 I1 C24 C25 -11.2(5) 4_466 . . . ? N14 I1 C24 C23 167.7(2) 4_466 . . . ? C23 C24 C25 F25 179.29(19) . . . . ? I1 C24 C25 F25 -1.7(3) . . . . ? C23 C24 C25 C26 -1.0(3) . . . . ? I1 C24 C25 C26 178.02(17) . . . . ? F25 C25 C26 F26 -0.6(3) . . . . ? C24 C25 C26 F26 179.7(2) . . . . ? F25 C25 C26 C21 -179.3(2) . . . . ? C24 C25 C26 C21 1.0(3) . . . . ? C22 C21 C26 F26 -178.78(19) . . . . ? C27 C21 C26 F26 0.8(3) . . . . ? C22 C21 C26 C25 -0.2(3) . . . . ? C27 C21 C26 C25 179.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A O22 0.83(3) 2.30(3) 3.084(3) 158(3) . N12 H12B O22 0.79(3) 2.22(3) 2.904(2) 144(3) 3_666 O21 H21 N11 0.77(3) 1.87(3) 2.635(2) 168(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.485 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.136 #END data_pc0808m _database_code_depnum_ccdc_archive 'CCDC 809431' #TrackingRef '- allrevised.cif' #A2B2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; P39 4-Br-2,3,5,6-F4-PhCOOH, 2-Br-5-NH2-pyrazine ; _chemical_name_common 'P39 4-Br-2,3,5,6-F4-PhCOOH, 2-Br-5-NH2-pyrazine' _chemical_melting_point ? _chemical_formula_moiety ; C7 H Br F4 O2, C4 H4 Br N3 ; _chemical_formula_sum 'C11 H5 Br2 F4 N3 O2' _chemical_formula_weight 447.00 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' Br Br -0.2901 2.4595 '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 7.1539(4) _cell_length_b 9.6066(5) _cell_length_c 10.2884(6) _cell_angle_alpha 89.546(4) _cell_angle_beta 73.888(3) _cell_angle_gamma 83.695(3) _cell_volume 675.00(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4689 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 31.84 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 6.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4083 _exptl_absorpt_correction_T_max 0.5824 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9855 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 32.03 _reflns_number_total 3975 _reflns_number_gt 3084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.7000P] 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 3975 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 -0.69658(4) 0.25844(3) 0.84022(3) 0.02177(10) Uani 1 1 d . . . Br2 Br 0.86253(4) 0.02682(3) -0.14622(3) 0.02111(10) Uani 1 1 d . . . N11 N 0.9053(4) 0.2511(3) 0.0067(3) 0.0206(5) Uani 1 1 d . . . C12 C 0.7873(4) 0.1546(3) 0.0033(3) 0.0187(6) Uani 1 1 d . . . C13 C 0.6178(5) 0.1439(4) 0.1049(3) 0.0206(6) Uani 1 1 d . . . H13 H 0.5354 0.0751 0.0971 0.025 Uiso 1 1 calc R . . N14 N 0.5674(4) 0.2290(3) 0.2145(3) 0.0217(6) Uani 1 1 d . . . C15 C 0.6882(4) 0.3238(3) 0.2235(3) 0.0198(6) Uani 1 1 d . . . N15 N 0.6432(4) 0.4051(3) 0.3360(3) 0.0234(6) Uani 1 1 d . . . H15A H 0.5366 0.3955 0.4016 0.028 Uiso 1 1 calc R . . H15B H 0.7202 0.4679 0.3440 0.028 Uiso 1 1 calc R . . C16 C 0.8579(4) 0.3347(3) 0.1151(3) 0.0214(6) Uani 1 1 d . . . H16 H 0.9403 0.4043 0.1203 0.026 Uiso 1 1 calc R . . C21 C -0.0553(4) 0.2824(3) 0.5618(3) 0.0185(6) Uani 1 1 d . . . C27 C 0.1507(4) 0.2899(3) 0.4786(3) 0.0203(6) Uani 1 1 d . . . O21 O 0.2072(3) 0.2073(3) 0.3722(3) 0.0315(6) Uani 1 1 d . . . H21 H 0.3241 0.2163 0.3310 0.038 Uiso 1 1 calc R . . O22 O 0.2542(3) 0.3694(3) 0.5088(3) 0.0302(6) Uani 1 1 d . . . C22 C -0.1388(4) 0.3714(3) 0.6744(3) 0.0185(6) Uani 1 1 d . . . F22 F -0.0398(3) 0.4703(2) 0.7078(2) 0.0265(4) Uani 1 1 d . . . C23 C -0.3260(4) 0.3660(3) 0.7563(3) 0.0188(6) Uani 1 1 d . . . F23 F -0.3937(3) 0.4535(2) 0.8637(2) 0.0250(4) Uani 1 1 d . . . C24 C -0.4433(4) 0.2706(3) 0.7288(3) 0.0187(6) Uani 1 1 d . . . C25 C -0.3655(5) 0.1830(4) 0.6169(3) 0.0209(6) Uani 1 1 d . . . F25 F -0.4731(3) 0.0893(2) 0.5861(2) 0.0307(5) Uani 1 1 d . . . C26 C -0.1769(4) 0.1884(3) 0.5354(3) 0.0207(6) Uani 1 1 d . . . F26 F -0.1175(3) 0.0987(2) 0.4295(2) 0.0282(5) 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 Br1 0.01423(15) 0.02600(17) 0.02125(18) -0.00508(12) 0.00285(11) -0.00565(11) Br2 0.01886(15) 0.02412(17) 0.01799(17) -0.00754(12) -0.00106(11) -0.00232(11) N11 0.0159(12) 0.0236(13) 0.0202(14) -0.0045(10) 0.0001(10) -0.0057(10) C12 0.0155(13) 0.0221(15) 0.0163(15) -0.0058(11) -0.0006(11) -0.0028(11) C13 0.0182(14) 0.0246(15) 0.0176(15) -0.0082(12) -0.0011(11) -0.0059(12) N14 0.0155(12) 0.0252(14) 0.0207(14) -0.0072(11) 0.0030(10) -0.0067(10) C15 0.0145(13) 0.0241(15) 0.0185(15) -0.0046(12) 0.0001(11) -0.0049(11) N15 0.0185(12) 0.0286(14) 0.0198(14) -0.0082(11) 0.0027(10) -0.0092(11) C16 0.0171(14) 0.0250(16) 0.0199(16) -0.0061(12) 0.0005(11) -0.0066(12) C21 0.0150(13) 0.0230(15) 0.0159(14) -0.0041(11) -0.0006(11) -0.0049(11) C27 0.0158(13) 0.0255(16) 0.0161(15) -0.0046(12) 0.0007(11) -0.0002(11) O21 0.0176(11) 0.0415(15) 0.0279(14) -0.0204(11) 0.0102(9) -0.0131(10) O22 0.0178(11) 0.0433(15) 0.0259(13) -0.0157(11) 0.0049(9) -0.0149(11) C22 0.0169(13) 0.0189(14) 0.0197(15) -0.0061(11) -0.0033(11) -0.0051(11) F22 0.0184(9) 0.0289(10) 0.0298(11) -0.0150(8) 0.0006(8) -0.0101(8) C23 0.0179(13) 0.0225(15) 0.0141(14) -0.0080(11) -0.0008(10) -0.0030(11) F23 0.0194(9) 0.0300(11) 0.0218(10) -0.0146(8) 0.0014(7) -0.0033(8) C24 0.0134(12) 0.0219(15) 0.0181(15) -0.0040(12) 0.0010(10) -0.0047(11) C25 0.0181(14) 0.0259(16) 0.0181(15) -0.0054(12) -0.0020(11) -0.0075(12) F25 0.0204(9) 0.0354(11) 0.0335(12) -0.0176(9) 0.0017(8) -0.0143(8) C26 0.0194(14) 0.0254(16) 0.0153(15) -0.0103(12) 0.0000(11) -0.0056(12) F26 0.0226(9) 0.0342(11) 0.0233(10) -0.0195(9) 0.0034(8) -0.0083(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 Br1 C24 1.871(3) . ? Br1 N11 2.896(3) 1_356 ? Br2 C12 1.894(3) . ? N11 C16 1.322(4) . ? N11 C12 1.328(4) . ? C12 C13 1.377(4) . ? C13 N14 1.340(4) . ? C13 H13 0.9500 . ? N14 C15 1.343(4) . ? C15 N15 1.343(4) . ? C15 C16 1.416(4) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? C16 H16 0.9500 . ? C21 C22 1.395(4) . ? C21 C26 1.398(4) . ? C21 C27 1.493(4) . ? C27 O22 1.218(4) . ? C27 O21 1.300(4) . ? O21 H21 0.8400 . ? C22 F22 1.346(3) . ? C22 C23 1.377(4) . ? C23 F23 1.339(3) . ? C23 C24 1.388(4) . ? C24 C25 1.379(4) . ? C25 F25 1.340(4) . ? C25 C26 1.383(4) . ? C26 F26 1.338(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 Br1 N11 177.33(12) . 1_356 ? C16 N11 C12 117.3(3) . . ? N11 C12 C13 122.2(3) . . ? N11 C12 Br2 117.6(2) . . ? C13 C12 Br2 120.2(2) . . ? N14 C13 C12 121.0(3) . . ? N14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 N14 C15 118.1(3) . . ? N14 C15 N15 118.5(3) . . ? N14 C15 C16 119.2(3) . . ? N15 C15 C16 122.3(3) . . ? C15 N15 H15A 120.0 . . ? C15 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? N11 C16 C15 122.1(3) . . ? N11 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C22 C21 C26 115.3(3) . . ? C22 C21 C27 120.8(3) . . ? C26 C21 C27 123.9(3) . . ? O22 C27 O21 123.6(3) . . ? O22 C27 C21 121.7(3) . . ? O21 C27 C21 114.7(3) . . ? C27 O21 H21 109.5 . . ? F22 C22 C23 115.8(3) . . ? F22 C22 C21 121.2(3) . . ? C23 C22 C21 122.9(3) . . ? F23 C23 C22 119.1(3) . . ? F23 C23 C24 120.2(3) . . ? C22 C23 C24 120.7(3) . . ? C25 C24 C23 117.6(3) . . ? C25 C24 Br1 120.8(2) . . ? C23 C24 Br1 121.7(2) . . ? F25 C25 C24 119.8(3) . . ? F25 C25 C26 118.8(3) . . ? C24 C25 C26 121.5(3) . . ? F26 C26 C25 116.1(3) . . ? F26 C26 C21 121.8(3) . . ? C25 C26 C21 122.0(3) . . ? 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 C16 N11 C12 C13 2.5(5) . . . . ? C16 N11 C12 Br2 -176.2(3) . . . . ? N11 C12 C13 N14 -1.9(5) . . . . ? Br2 C12 C13 N14 176.7(3) . . . . ? C12 C13 N14 C15 -0.9(5) . . . . ? C13 N14 C15 N15 -177.0(3) . . . . ? C13 N14 C15 C16 2.9(5) . . . . ? C12 N11 C16 C15 -0.4(5) . . . . ? N14 C15 C16 N11 -2.4(5) . . . . ? N15 C15 C16 N11 177.5(3) . . . . ? C22 C21 C27 O22 2.8(5) . . . . ? C26 C21 C27 O22 -176.8(4) . . . . ? C22 C21 C27 O21 -176.1(3) . . . . ? C26 C21 C27 O21 4.3(5) . . . . ? C26 C21 C22 F22 -177.4(3) . . . . ? C27 C21 C22 F22 2.9(5) . . . . ? C26 C21 C22 C23 1.4(5) . . . . ? C27 C21 C22 C23 -178.2(3) . . . . ? F22 C22 C23 F23 -2.3(5) . . . . ? C21 C22 C23 F23 178.8(3) . . . . ? F22 C22 C23 C24 178.1(3) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? F23 C23 C24 C25 -179.9(3) . . . . ? C22 C23 C24 C25 -0.3(5) . . . . ? F23 C23 C24 Br1 -0.8(5) . . . . ? C22 C23 C24 Br1 178.8(3) . . . . ? N11 Br1 C24 C25 -103(2) 1_356 . . . ? N11 Br1 C24 C23 78(3) 1_356 . . . ? C23 C24 C25 F25 -179.9(3) . . . . ? Br1 C24 C25 F25 1.0(5) . . . . ? C23 C24 C25 C26 0.7(5) . . . . ? Br1 C24 C25 C26 -178.4(3) . . . . ? F25 C25 C26 F26 0.8(5) . . . . ? C24 C25 C26 F26 -179.8(3) . . . . ? F25 C25 C26 C21 -179.4(3) . . . . ? C24 C25 C26 C21 0.0(6) . . . . ? C22 C21 C26 F26 178.8(3) . . . . ? C27 C21 C26 F26 -1.6(5) . . . . ? C22 C21 C26 C25 -1.0(5) . . . . ? C27 C21 C26 C25 178.6(3) . . . . ? 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 N15 H15A O21 0.88 3.20 3.758(3) 123.3 . N15 H15B O22 0.88 2.24 2.973(4) 140.4 2_666 O21 H21 N14 0.84 1.83 2.666(3) 170.0 . _diffrn_measured_fraction_theta_max 0.844 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 2.207 _refine_diff_density_min -1.296 _refine_diff_density_rms 0.153 #END data_pc0803m _database_code_depnum_ccdc_archive 'CCDC 809432' #TrackingRef '- allrevised.cif' #A1B3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; P10 3-amino-2,6-dibromopyrazine, 4-I-F4-PhCOOH ; _chemical_name_common 'P10 3-amino-2,6-dibromopyrazine, 4-I-F4-PhCOOH' _chemical_melting_point ? _chemical_formula_moiety ; C4 H3 Br2 N3, C7 H F4 I O2 ; _chemical_formula_sum 'C11 H4 Br2 F4 I N3 O2' _chemical_formula_weight 572.89 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4824(4) _cell_length_b 5.7580(3) _cell_length_c 25.7816(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.9360(10) _cell_angle_gamma 90.00 _cell_volume 1537.23(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8862 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 32.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 7.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2614 _exptl_absorpt_correction_T_max 0.4058 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17435 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 32.48 _reflns_number_total 5467 _reflns_number_gt 4867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5467 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0559 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 I1 I 1.085610(12) -0.95203(2) 0.110281(6) 0.02205(4) Uani 1 1 d . . . Br1 Br 0.22808(2) 0.58079(3) 0.212709(8) 0.02045(5) Uani 1 1 d . . . Br2 Br 0.34975(2) 0.84276(3) 0.021194(7) 0.02092(5) Uani 1 1 d . . . N11 N 0.47346(15) 0.2996(3) 0.12012(6) 0.0162(3) Uani 1 1 d . . . C12 C 0.40950(17) 0.3366(3) 0.16076(7) 0.0146(3) Uani 1 1 d . . . N12 N 0.43099(17) 0.1944(3) 0.20257(7) 0.0206(3) Uani 1 1 d . . . H12A H 0.473(3) 0.069(5) 0.1999(11) 0.025 Uiso 1 1 d . . . H12B H 0.386(3) 0.207(5) 0.2273(11) 0.025 Uiso 1 1 d . . . C13 C 0.32176(17) 0.5280(3) 0.15715(7) 0.0146(3) Uani 1 1 d . . . N14 N 0.30262(15) 0.6702(3) 0.11712(6) 0.0153(3) Uani 1 1 d . . . C15 C 0.36981(18) 0.6298(3) 0.07775(7) 0.0159(3) Uani 1 1 d . . . C16 C 0.45381(19) 0.4444(3) 0.07885(7) 0.0175(3) Uani 1 1 d . . . H16 H 0.4983 0.4189 0.0500 0.021 Uiso 1 1 calc R . . C21 C 0.76164(17) -0.3580(3) 0.13421(7) 0.0148(3) Uani 1 1 d . . . C27 C 0.66201(17) -0.1810(3) 0.14338(7) 0.0156(3) Uani 1 1 d . . . O21 O 0.65741(15) -0.0023(3) 0.11165(6) 0.0229(3) Uani 1 1 d . . . H21 H 0.596(3) 0.088(5) 0.1184(12) 0.034 Uiso 1 1 d . . . O22 O 0.59430(13) -0.2067(2) 0.17747(5) 0.0183(3) Uani 1 1 d . . . C22 C 0.82199(18) -0.4929(3) 0.17589(7) 0.0163(3) Uani 1 1 d . . . F22 F 0.79665(13) -0.4591(2) 0.22468(5) 0.0237(3) Uani 1 1 d . . . C23 C 0.91187(18) -0.6617(3) 0.16881(7) 0.0177(3) Uani 1 1 d . . . F23 F 0.96430(13) -0.7880(2) 0.21059(5) 0.0275(3) Uani 1 1 d . . . C24 C 0.94785(17) -0.7009(3) 0.11994(8) 0.0174(3) Uani 1 1 d . . . C25 C 0.88959(19) -0.5661(3) 0.07849(8) 0.0186(3) Uani 1 1 d . . . F25 F 0.92138(14) -0.5941(2) 0.03047(5) 0.0289(3) Uani 1 1 d . . . C26 C 0.79716(19) -0.4001(3) 0.08510(7) 0.0186(3) Uani 1 1 d . . . F26 F 0.74139(14) -0.2855(2) 0.04244(5) 0.0291(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 I1 0.01509(6) 0.01737(6) 0.03465(8) -0.00226(5) 0.00688(5) 0.00478(4) Br1 0.02215(10) 0.02303(9) 0.01839(9) 0.00147(7) 0.01013(7) 0.00735(7) Br2 0.02705(10) 0.01964(9) 0.01712(8) 0.00484(6) 0.00674(7) 0.00723(7) N11 0.0170(7) 0.0161(6) 0.0165(7) -0.0001(5) 0.0050(5) 0.0050(6) C12 0.0142(8) 0.0145(7) 0.0155(7) 0.0002(6) 0.0036(6) 0.0022(6) N12 0.0247(9) 0.0203(7) 0.0182(7) 0.0046(6) 0.0081(6) 0.0095(6) C13 0.0144(8) 0.0148(7) 0.0154(7) -0.0014(6) 0.0050(6) 0.0020(6) N14 0.0152(7) 0.0153(6) 0.0161(7) -0.0013(5) 0.0050(5) 0.0023(5) C15 0.0172(8) 0.0157(7) 0.0150(7) 0.0015(6) 0.0037(6) 0.0029(6) C16 0.0193(9) 0.0170(8) 0.0175(8) 0.0001(6) 0.0074(7) 0.0043(6) C21 0.0124(7) 0.0150(7) 0.0174(8) 0.0017(6) 0.0034(6) 0.0020(6) C27 0.0144(8) 0.0149(7) 0.0173(8) 0.0001(6) 0.0023(6) 0.0015(6) O21 0.0228(7) 0.0188(6) 0.0297(7) 0.0081(6) 0.0126(6) 0.0096(5) O22 0.0181(6) 0.0191(6) 0.0187(6) 0.0006(5) 0.0062(5) 0.0045(5) C22 0.0157(8) 0.0178(7) 0.0161(8) 0.0010(6) 0.0047(6) 0.0026(6) F22 0.0275(6) 0.0287(6) 0.0158(5) 0.0034(4) 0.0064(5) 0.0097(5) C23 0.0131(8) 0.0185(8) 0.0216(8) 0.0055(6) 0.0030(6) 0.0048(6) F23 0.0261(6) 0.0306(6) 0.0265(6) 0.0130(5) 0.0065(5) 0.0148(5) C24 0.0115(7) 0.0156(7) 0.0259(9) 0.0010(7) 0.0057(6) 0.0027(6) C25 0.0172(8) 0.0208(8) 0.0194(8) 0.0001(6) 0.0083(7) 0.0032(7) F25 0.0319(7) 0.0364(7) 0.0214(6) 0.0018(5) 0.0137(5) 0.0110(6) C26 0.0193(9) 0.0194(8) 0.0179(8) 0.0038(6) 0.0054(7) 0.0059(7) F26 0.0376(7) 0.0333(7) 0.0172(5) 0.0083(5) 0.0067(5) 0.0180(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C24 2.0857(18) . ? I1 N14 3.1325(15) 1_635 ? Br1 C13 1.8828(17) . ? Br2 C15 1.8917(18) . ? N11 C16 1.342(2) . ? N11 C12 1.346(2) . ? C12 N12 1.344(2) . ? C12 C13 1.430(2) . ? N12 H12A 0.86(3) . ? N12 H12B 0.85(3) . ? C13 N14 1.308(2) . ? N14 C15 1.342(2) . ? C15 C16 1.382(2) . ? C16 H16 0.9500 . ? C21 C26 1.395(2) . ? C21 C22 1.396(3) . ? C21 C27 1.504(2) . ? C27 O22 1.221(2) . ? C27 O21 1.311(2) . ? O21 H21 0.86(3) . ? C22 F22 1.340(2) . ? C22 C23 1.385(2) . ? C23 F23 1.344(2) . ? C23 C24 1.389(3) . ? C24 C25 1.383(3) . ? C25 F25 1.341(2) . ? C25 C26 1.390(3) . ? C26 F26 1.337(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 C24 I1 N14 170.04(6) . 1_635 ? C16 N11 C12 119.03(15) . . ? N12 C12 N11 119.10(16) . . ? N12 C12 C13 123.21(16) . . ? N11 C12 C13 117.70(15) . . ? C12 N12 H12A 118.3(18) . . ? C12 N12 H12B 120.3(18) . . ? H12A N12 H12B 119(3) . . ? N14 C13 C12 123.51(15) . . ? N14 C13 Br1 117.72(13) . . ? C12 C13 Br1 118.77(13) . . ? C13 N14 C15 117.00(15) . . ? N14 C15 C16 121.73(16) . . ? N14 C15 Br2 117.51(13) . . ? C16 C15 Br2 120.73(13) . . ? N11 C16 C15 121.01(16) . . ? N11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C26 C21 C22 116.68(16) . . ? C26 C21 C27 123.38(16) . . ? C22 C21 C27 119.93(16) . . ? O22 C27 O21 125.10(17) . . ? O22 C27 C21 121.78(16) . . ? O21 C27 C21 113.13(15) . . ? C27 O21 H21 108(2) . . ? F22 C22 C23 117.64(16) . . ? F22 C22 C21 120.65(16) . . ? C23 C22 C21 121.69(16) . . ? F23 C23 C22 118.40(16) . . ? F23 C23 C24 120.30(16) . . ? C22 C23 C24 121.30(17) . . ? C25 C24 C23 117.40(16) . . ? C25 C24 I1 121.83(13) . . ? C23 C24 I1 120.76(14) . . ? F25 C25 C24 120.17(16) . . ? F25 C25 C26 118.26(17) . . ? C24 C25 C26 121.56(17) . . ? F26 C26 C25 117.55(16) . . ? F26 C26 C21 121.11(16) . . ? C25 C26 C21 121.33(17) . . ? 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 C16 N11 C12 N12 -178.71(18) . . . . ? C16 N11 C12 C13 1.0(3) . . . . ? N12 C12 C13 N14 178.37(18) . . . . ? N11 C12 C13 N14 -1.3(3) . . . . ? N12 C12 C13 Br1 -1.6(3) . . . . ? N11 C12 C13 Br1 178.71(13) . . . . ? C12 C13 N14 C15 0.3(3) . . . . ? Br1 C13 N14 C15 -179.78(14) . . . . ? C13 N14 C15 C16 1.1(3) . . . . ? C13 N14 C15 Br2 -176.91(13) . . . . ? C12 N11 C16 C15 0.3(3) . . . . ? N14 C15 C16 N11 -1.4(3) . . . . ? Br2 C15 C16 N11 176.54(14) . . . . ? C26 C21 C27 O22 149.07(19) . . . . ? C22 C21 C27 O22 -29.7(3) . . . . ? C26 C21 C27 O21 -31.2(3) . . . . ? C22 C21 C27 O21 149.98(18) . . . . ? C26 C21 C22 F22 177.90(17) . . . . ? C27 C21 C22 F22 -3.2(3) . . . . ? C26 C21 C22 C23 -0.5(3) . . . . ? C27 C21 C22 C23 178.35(17) . . . . ? F22 C22 C23 F23 2.7(3) . . . . ? C21 C22 C23 F23 -178.79(17) . . . . ? F22 C22 C23 C24 -177.18(17) . . . . ? C21 C22 C23 C24 1.3(3) . . . . ? F23 C23 C24 C25 179.55(18) . . . . ? C22 C23 C24 C25 -0.6(3) . . . . ? F23 C23 C24 I1 -0.9(3) . . . . ? C22 C23 C24 I1 178.96(14) . . . . ? N14 I1 C24 C25 166.7(3) 1_635 . . . ? N14 I1 C24 C23 -12.8(4) 1_635 . . . ? C23 C24 C25 F25 179.26(17) . . . . ? I1 C24 C25 F25 -0.2(3) . . . . ? C23 C24 C25 C26 -0.9(3) . . . . ? I1 C24 C25 C26 179.55(15) . . . . ? F25 C25 C26 F26 2.9(3) . . . . ? C24 C25 C26 F26 -176.86(18) . . . . ? F25 C25 C26 C21 -178.47(18) . . . . ? C24 C25 C26 C21 1.7(3) . . . . ? C22 C21 C26 F26 177.59(18) . . . . ? C27 C21 C26 F26 -1.3(3) . . . . ? C22 C21 C26 C25 -0.9(3) . . . . ? C27 C21 C26 C25 -179.79(18) . . . . ? 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 O21 H21 N11 0.86(3) 1.78(3) 2.630(2) 169(3) . N12 H12A O22 0.86(3) 2.17(3) 3.005(2) 166(3) . N12 H12B O22 0.85(3) 2.48(3) 3.196(2) 142(2) 2_655 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 32.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.367 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.104 #END data_pc1020m _database_code_depnum_ccdc_archive 'CCDC 809433' #TrackingRef '- allrevised.cif' #A2B3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; PC-4-7d 2-amino-3,5-dibromopyrazine, 4-Br-F4-PhCOOH ; _chemical_name_common 'PC-4-7d 2-amino-3,5-dibromopyrazine, 4-Br-F4-PhCOOH' _chemical_melting_point ? _chemical_formula_moiety ; C4 H3 Br2 N3, C7 H Br F4 O2 ; _chemical_formula_sum 'C11 H4 Br3 F4 N3 O2' _chemical_formula_weight 525.90 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' Br Br -0.2901 2.4595 '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 15.2443(14) _cell_length_b 13.9577(16) _cell_length_c 21.995(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.743(6) _cell_angle_gamma 90.00 _cell_volume 4405.0(8) _cell_formula_units_Z 12 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3769 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 26.86 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2976 _exptl_absorpt_coefficient_mu 8.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2047 _exptl_absorpt_correction_T_max 0.4908 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 45126 _diffrn_reflns_av_R_equivalents 0.1747 _diffrn_reflns_av_sigmaI/netI 0.1609 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 29.57 _reflns_number_total 12261 _reflns_number_gt 6482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The SHELX "SAME" command was used to restrain the geometries of the three crystallographically independent halobenzoic acid molecules. The "SAME" command was also used to restrain the geometries of the three independent aminopyrazine molecules. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12261 _refine_ls_number_parameters 298 _refine_ls_number_restraints 198 _refine_ls_R_factor_all 0.2491 _refine_ls_R_factor_gt 0.1678 _refine_ls_wR_factor_ref 0.3995 _refine_ls_wR_factor_gt 0.3734 _refine_ls_goodness_of_fit_ref 1.808 _refine_ls_restrained_S_all 1.797 _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_1 Br 0.33893(13) 0.01156(15) 0.33674(11) 0.0339(5) Uani 1 1 d . . . Br2_1 Br 0.34715(13) 0.40344(16) 0.36468(12) 0.0374(6) Uani 1 1 d . . . Br3_1 Br -0.47381(11) 0.20640(16) 0.35990(9) 0.0257(5) Uani 1 1 d . . . N11_1 N 0.1496(8) 0.2038(10) 0.3639(5) 0.0211(13) Uani 1 1 d DU . . C12_1 C 0.1908(9) 0.1189(11) 0.3574(3) 0.0211(13) Uani 1 1 d D . . N12_1 N 0.1465(9) 0.0354(10) 0.3559(5) 0.0211(13) Uani 1 1 d D . . H12A_1 H 0.0905 0.0348 0.3592 0.025 Uiso 1 1 calc R . . H12B_1 H 0.1734 -0.0188 0.3517 0.025 Uiso 1 1 calc R . . C13_1 C 0.2805(9) 0.1250(12) 0.3524(5) 0.0211(13) Uani 1 1 d D . . N14_1 N 0.3266(9) 0.2058(10) 0.3537(5) 0.0211(13) Uani 1 1 d D . . C15_1 C 0.2821(9) 0.2844(12) 0.3601(5) 0.0211(13) Uani 1 1 d D . . C16_1 C 0.1948(10) 0.2843(12) 0.3651(5) 0.0211(13) Uani 1 1 d D . . H16_1 H 0.1667 0.3434 0.3696 0.025 Uiso 1 1 calc R . . C21_1 C -0.1648(9) 0.1716(10) 0.3651(3) 0.0286(9) Uani 1 1 d D . . C22_1 C -0.2294(9) 0.0997(11) 0.3467(3) 0.0286(9) Uani 1 1 d D . . F22_1 F -0.2032(7) 0.0128(7) 0.3302(4) 0.0286(9) Uani 1 1 d D . . C23_1 C -0.3216(9) 0.1103(11) 0.3437(4) 0.0286(9) Uani 1 1 d D . . F23_1 F -0.3798(6) 0.0350(8) 0.3248(4) 0.0286(9) Uani 1 1 d D . . C24_1 C -0.3512(10) 0.1954(11) 0.3595(4) 0.0286(9) Uani 1 1 d D . . C25_1 C -0.2902(9) 0.2696(11) 0.3782(4) 0.0286(9) Uani 1 1 d D . . F25_1 F -0.3164(6) 0.3547(7) 0.3943(4) 0.0286(9) Uani 1 1 d D . . C26_1 C -0.1997(9) 0.2591(11) 0.3811(4) 0.0286(9) Uani 1 1 d D . . F26_1 F -0.1422(6) 0.3331(8) 0.3996(4) 0.0286(9) Uani 1 1 d D . . C27_1 C -0.0645(9) 0.1596(10) 0.3686(3) 0.0286(9) Uani 1 1 d D . . O21_1 O -0.0230(8) 0.2308(9) 0.3597(6) 0.0286(9) Uani 1 1 d D . . H21_1 H 0.0309 0.2152 0.3611 0.034 Uiso 1 1 calc R . . O22_1 O -0.0315(8) 0.0755(9) 0.3807(6) 0.0286(9) Uani 1 1 d D . . Br4_2 Br 0.54786(13) 0.35417(15) 0.20972(11) 0.0317(5) Uani 1 1 d . . . Br5_2 Br 0.51768(12) -0.03219(15) 0.15810(10) 0.0302(5) Uani 1 1 d . . . Br6_2 Br -0.28988(11) 0.16709(14) 0.18725(8) 0.0216(4) Uani 1 1 d . . . N11_2 N 0.3344(8) 0.1616(10) 0.1908(5) 0.0225(13) Uani 1 1 d DU . . C12_2 C 0.3866(9) 0.2448(11) 0.2005(4) 0.0225(13) Uani 1 1 d D . . N12_2 N 0.3491(10) 0.3268(10) 0.2143(6) 0.0225(13) Uani 1 1 d D . . H12A_2 H 0.2927 0.3262 0.2168 0.027 Uiso 1 1 calc R . . H12B_2 H 0.3812 0.3805 0.2207 0.027 Uiso 1 1 calc R . . C13_2 C 0.4758(9) 0.2404(12) 0.1957(5) 0.0225(13) Uani 1 1 d D . . N14_2 N 0.5122(9) 0.1598(10) 0.1822(5) 0.0225(13) Uani 1 1 d D . . C15_2 C 0.4602(9) 0.0835(12) 0.1734(5) 0.0225(13) Uani 1 1 d D . . C16_2 C 0.3727(10) 0.0825(12) 0.1774(6) 0.0225(13) Uani 1 1 d D . . H16_2 H 0.3386 0.0241 0.1704 0.027 Uiso 1 1 calc R . . C21_2 C 0.0234(9) 0.1993(11) 0.1983(3) 0.0400(12) Uani 1 1 d D . . C22_2 C -0.0331(9) 0.2764(12) 0.1981(3) 0.0400(12) Uani 1 1 d D . . F22_2 F 0.0004(6) 0.3668(8) 0.2007(4) 0.0400(12) Uani 1 1 d D . . C23_2 C -0.1244(9) 0.2667(12) 0.1953(4) 0.0400(12) Uani 1 1 d D . . F23_2 F -0.1747(7) 0.3459(8) 0.1953(5) 0.0400(12) Uani 1 1 d D . . C24_2 C -0.1618(10) 0.1773(12) 0.1926(4) 0.0400(12) Uani 1 1 d D . . C25_2 C -0.1079(9) 0.1001(12) 0.1928(4) 0.0400(12) Uani 1 1 d D . . F25_2 F -0.1461(7) 0.0134(8) 0.1900(5) 0.0400(12) Uani 1 1 d D . . C26_2 C -0.0187(9) 0.1074(11) 0.1955(3) 0.0400(12) Uani 1 1 d D . . F26_2 F 0.0281(7) 0.0271(8) 0.1954(4) 0.0400(12) Uani 1 1 d D . . C27_2 C 0.1230(9) 0.2107(11) 0.2014(4) 0.0400(12) Uani 1 1 d D . . O21_2 O 0.1632(8) 0.1375(10) 0.1917(7) 0.0400(12) Uani 1 1 d D . . H21_2 H 0.2169 0.1520 0.1921 0.048 Uiso 1 1 calc R . . O22_2 O 0.1590(8) 0.2930(10) 0.2133(7) 0.0400(12) Uani 1 1 d D . . Br7_3 Br 0.69658(13) 0.42662(15) 0.02502(11) 0.0313(5) Uani 1 1 d . . . Br8_3 Br 0.68294(12) 0.03369(15) 0.00855(10) 0.0297(5) Uani 1 1 d . . . Br9_3 Br -0.12774(11) 0.23035(15) 0.02697(9) 0.0233(4) Uani 1 1 d . . . N11_3 N 0.4969(8) 0.2324(10) 0.0309(5) 0.0211(13) Uani 1 1 d DU . . C12_3 C 0.5456(9) 0.3172(11) 0.0335(3) 0.0211(13) Uani 1 1 d D . . N12_3 N 0.5029(9) 0.3985(10) 0.0416(6) 0.0211(13) Uani 1 1 d D . . H12A_3 H 0.4470 0.3960 0.0450 0.025 Uiso 1 1 calc R . . H12B_3 H 0.5310 0.4541 0.0436 0.025 Uiso 1 1 calc R . . C13_3 C 0.6337(9) 0.3109(12) 0.0275(5) 0.0211(13) Uani 1 1 d D . . N14_3 N 0.6722(9) 0.2292(10) 0.0197(5) 0.0211(13) Uani 1 1 d D . . C15_3 C 0.6250(9) 0.1505(12) 0.0174(5) 0.0211(13) Uani 1 1 d D . . C16_3 C 0.5384(9) 0.1520(12) 0.0229(6) 0.0211(13) Uani 1 1 d D . . H16_3 H 0.5064 0.0931 0.0209 0.025 Uiso 1 1 calc R . . C21_3 C 0.1846(9) 0.2665(11) 0.0368(3) 0.0302(10) Uani 1 1 d D . . C22_3 C 0.1231(9) 0.3419(11) 0.0251(3) 0.0302(10) Uani 1 1 d D . . F22_3 F 0.1519(6) 0.4304(8) 0.0174(4) 0.0302(10) Uani 1 1 d D . . C23_3 C 0.0308(9) 0.3310(11) 0.0207(3) 0.0302(10) Uani 1 1 d D . . F23_3 F -0.0249(6) 0.4084(8) 0.0091(4) 0.0302(10) Uani 1 1 d D . . C24_3 C -0.0030(10) 0.2427(11) 0.0280(4) 0.0302(10) Uani 1 1 d D . . C25_3 C 0.0558(9) 0.1655(11) 0.0398(3) 0.0302(10) Uani 1 1 d D . . F25_3 F 0.0245(7) 0.0777(7) 0.0473(4) 0.0302(10) Uani 1 1 d D . . C26_3 C 0.1462(9) 0.1757(11) 0.0441(3) 0.0302(10) Uani 1 1 d D . . F26_3 F 0.2000(6) 0.0978(8) 0.0555(4) 0.0302(10) Uani 1 1 d D . . C27_3 C 0.2858(9) 0.2780(10) 0.0419(4) 0.0302(10) Uani 1 1 d D . . O21_3 O 0.3250(8) 0.2071(9) 0.0298(6) 0.0302(10) Uani 1 1 d D . . H21_3 H 0.3786 0.2223 0.0305 0.036 Uiso 1 1 calc R . . O22_3 O 0.3209(8) 0.3603(9) 0.0583(6) 0.0302(10) Uani 1 1 d 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 Br1_1 0.0244(10) 0.0142(10) 0.0728(15) 0.0031(10) 0.0291(10) 0.0027(8) Br2_1 0.0192(9) 0.0168(11) 0.0769(15) -0.0082(10) 0.0168(9) -0.0054(8) Br3_1 0.0116(8) 0.0300(12) 0.0355(10) 0.0033(8) 0.0079(7) 0.0011(7) N11_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) C12_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) N12_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) C13_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) N14_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) C15_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) C16_1 0.0200(19) 0.020(2) 0.023(2) -0.0003(16) 0.0073(15) -0.0003(15) C21_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C22_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) F22_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C23_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) F23_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C24_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C25_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) F25_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C26_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) F26_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) C27_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) O21_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) O22_1 0.0172(19) 0.020(2) 0.053(3) 0.0025(19) 0.0173(17) 0.0004(16) Br4_2 0.0275(10) 0.0153(10) 0.0592(13) -0.0075(9) 0.0238(9) -0.0026(8) Br5_2 0.0118(8) 0.0171(10) 0.0577(13) -0.0066(9) 0.0066(8) 0.0056(7) Br6_2 0.0099(7) 0.0226(10) 0.0298(9) 0.0004(8) 0.0036(6) 0.0059(7) N11_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) C12_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) N12_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) C13_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) N14_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) C15_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) C16_2 0.0196(19) 0.022(2) 0.025(2) -0.0010(16) 0.0067(15) 0.0016(16) C21_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C22_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) F22_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C23_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) F23_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C24_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C25_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) F25_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C26_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) F26_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) C27_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) O21_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) O22_2 0.0137(19) 0.022(2) 0.091(4) -0.005(2) 0.026(2) 0.0014(17) Br7_3 0.0206(9) 0.0172(10) 0.0644(14) -0.0080(9) 0.0252(9) -0.0076(8) Br8_3 0.0129(8) 0.0156(10) 0.0635(13) 0.0026(9) 0.0169(8) 0.0053(7) Br9_3 0.0062(7) 0.0289(11) 0.0365(10) 0.0006(8) 0.0092(6) -0.0011(7) N11_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) C12_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) N12_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) C13_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) N14_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) C15_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) C16_3 0.0189(19) 0.021(2) 0.026(2) -0.0012(16) 0.0107(15) -0.0015(16) C21_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C22_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) F22_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C23_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) F23_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C24_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C25_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) F25_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C26_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) F26_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) C27_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) O21_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(15) O22_3 0.0135(18) 0.015(2) 0.064(3) 0.0017(19) 0.0164(18) -0.0019(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 Br1_1 C13_1 1.905(16) . ? Br2_1 C15_1 1.921(16) . ? Br3_1 C24_1 1.879(15) . ? Br3_1 N14_1 3.000(13) 1_455 ? N11_1 C16_1 1.314(17) . ? N11_1 C12_1 1.371(17) . ? C12_1 N12_1 1.342(17) . ? C12_1 C13_1 1.410(16) . ? N12_1 H12A_1 0.8800 . ? N12_1 H12B_1 0.8800 . ? C13_1 N14_1 1.324(17) . ? N14_1 C15_1 1.322(17) . ? C15_1 C16_1 1.372(16) . ? C16_1 H16_1 0.9500 . ? C21_1 C22_1 1.368(19) . ? C21_1 C26_1 1.424(19) . ? C21_1 C27_1 1.514(17) . ? C22_1 F22_1 1.363(16) . ? C22_1 C23_1 1.393(17) . ? C23_1 F23_1 1.347(16) . ? C23_1 C24_1 1.358(19) . ? C24_1 C25_1 1.358(19) . ? C25_1 F25_1 1.339(16) . ? C25_1 C26_1 1.366(16) . ? C26_1 F26_1 1.327(16) . ? C27_1 O21_1 1.229(15) . ? C27_1 O22_1 1.269(16) . ? O21_1 H21_1 0.8400 . ? Br4_2 C13_2 1.896(16) . ? Br5_2 C15_2 1.921(16) . ? Br6_2 C24_2 1.922(15) . ? Br6_2 N14_2 2.983(13) 1_455 ? N11_2 C16_2 1.328(17) . ? N11_2 C12_2 1.382(17) . ? C12_2 N12_2 1.359(17) . ? C12_2 C13_2 1.400(17) . ? N12_2 H12A_2 0.8800 . ? N12_2 H12B_2 0.8800 . ? C13_2 N14_2 1.332(17) . ? N14_2 C15_2 1.303(17) . ? C15_2 C16_2 1.365(16) . ? C16_2 H16_2 0.9500 . ? C21_2 C22_2 1.378(19) . ? C21_2 C26_2 1.43(2) . ? C21_2 C27_2 1.505(17) . ? C22_2 F22_2 1.356(17) . ? C22_2 C23_2 1.379(17) . ? C23_2 F23_2 1.346(16) . ? C23_2 C24_2 1.36(2) . ? C24_2 C25_2 1.354(19) . ? C25_2 F25_2 1.335(17) . ? C25_2 C26_2 1.344(16) . ? C26_2 F26_2 1.331(16) . ? C27_2 O21_2 1.246(16) . ? C27_2 O22_2 1.261(17) . ? O21_2 H21_2 0.8400 . ? Br7_3 C13_3 1.889(16) . ? Br8_3 C15_3 1.896(16) . ? Br9_3 C24_3 1.902(14) . ? Br9_3 N14_3 3.000(12) 1_455 ? N11_3 C16_3 1.328(17) . ? N11_3 C12_3 1.387(17) . ? C12_3 N12_3 1.350(17) . ? C12_3 C13_3 1.396(16) . ? N12_3 H12A_3 0.8800 . ? N12_3 H12B_3 0.8800 . ? C13_3 N14_3 1.320(17) . ? N14_3 C15_3 1.305(17) . ? C15_3 C16_3 1.365(16) . ? C16_3 H16_3 0.9500 . ? C21_3 C22_3 1.374(19) . ? C21_3 C26_3 1.427(19) . ? C21_3 C27_3 1.517(17) . ? C22_3 F22_3 1.341(16) . ? C22_3 C23_3 1.387(17) . ? C23_3 F23_3 1.343(16) . ? C23_3 C24_3 1.366(19) . ? C24_3 C25_3 1.369(19) . ? C25_3 F25_3 1.346(16) . ? C25_3 C26_3 1.357(16) . ? C26_3 F26_3 1.334(16) . ? C27_3 O21_3 1.231(15) . ? C27_3 O22_3 1.267(16) . ? O21_3 H21_3 0.8400 . ? 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 C24_1 Br3_1 N14_1 174.5(5) . 1_455 ? C16_1 N11_1 C12_1 119.1(13) . . ? N12_1 C12_1 N11_1 120.6(13) . . ? N12_1 C12_1 C13_1 123.0(14) . . ? N11_1 C12_1 C13_1 116.4(13) . . ? C12_1 N12_1 H12A_1 120.0 . . ? C12_1 N12_1 H12B_1 120.0 . . ? H12A_1 N12_1 H12B_1 120.0 . . ? N14_1 C13_1 C12_1 124.9(14) . . ? N14_1 C13_1 Br1_1 115.7(10) . . ? C12_1 C13_1 Br1_1 119.2(11) . . ? C15_1 N14_1 C13_1 114.9(13) . . ? N14_1 C15_1 C16_1 123.7(15) . . ? N14_1 C15_1 Br2_1 116.7(11) . . ? C16_1 C15_1 Br2_1 119.6(12) . . ? N11_1 C16_1 C15_1 121.0(15) . . ? N11_1 C16_1 H16_1 119.5 . . ? C15_1 C16_1 H16_1 119.5 . . ? C22_1 C21_1 C26_1 114.3(12) . . ? C22_1 C21_1 C27_1 123.2(12) . . ? C26_1 C21_1 C27_1 122.5(12) . . ? F22_1 C22_1 C21_1 119.0(12) . . ? F22_1 C22_1 C23_1 117.6(13) . . ? C21_1 C22_1 C23_1 123.4(14) . . ? F23_1 C23_1 C24_1 121.4(12) . . ? F23_1 C23_1 C22_1 118.8(13) . . ? C24_1 C23_1 C22_1 119.8(14) . . ? C23_1 C24_1 C25_1 119.5(14) . . ? C23_1 C24_1 Br3_1 119.3(11) . . ? C25_1 C24_1 Br3_1 121.1(12) . . ? F25_1 C25_1 C24_1 121.4(13) . . ? F25_1 C25_1 C26_1 118.0(13) . . ? C24_1 C25_1 C26_1 120.7(15) . . ? F26_1 C26_1 C25_1 119.0(14) . . ? F26_1 C26_1 C21_1 118.7(12) . . ? C25_1 C26_1 C21_1 122.4(14) . . ? O21_1 C27_1 O22_1 126.4(14) . . ? O21_1 C27_1 C21_1 117.9(12) . . ? O22_1 C27_1 C21_1 115.7(11) . . ? C27_1 O21_1 H21_1 109.5 . . ? C24_2 Br6_2 N14_2 177.4(5) . 1_455 ? C16_2 N11_2 C12_2 117.4(13) . . ? N12_2 C12_2 N11_2 118.6(13) . . ? N12_2 C12_2 C13_2 123.1(14) . . ? N11_2 C12_2 C13_2 118.3(13) . . ? C12_2 N12_2 H12A_2 120.0 . . ? C12_2 N12_2 H12B_2 120.0 . . ? H12A_2 N12_2 H12B_2 120.0 . . ? N14_2 C13_2 C12_2 122.9(14) . . ? N14_2 C13_2 Br4_2 118.7(11) . . ? C12_2 C13_2 Br4_2 118.4(11) . . ? C15_2 N14_2 C13_2 116.4(13) . . ? N14_2 C15_2 C16_2 123.9(15) . . ? N14_2 C15_2 Br5_2 114.9(11) . . ? C16_2 C15_2 Br5_2 121.1(12) . . ? N11_2 C16_2 C15_2 121.1(15) . . ? N11_2 C16_2 H16_2 119.4 . . ? C15_2 C16_2 H16_2 119.4 . . ? C22_2 C21_2 C26_2 115.4(12) . . ? C22_2 C21_2 C27_2 122.5(13) . . ? C26_2 C21_2 C27_2 122.0(13) . . ? F22_2 C22_2 C21_2 120.1(12) . . ? F22_2 C22_2 C23_2 117.0(13) . . ? C21_2 C22_2 C23_2 123.0(15) . . ? F23_2 C23_2 C24_2 121.5(13) . . ? F23_2 C23_2 C22_2 119.1(14) . . ? C24_2 C23_2 C22_2 119.4(14) . . ? C25_2 C24_2 C23_2 118.9(14) . . ? C25_2 C24_2 Br6_2 123.0(12) . . ? C23_2 C24_2 Br6_2 118.1(11) . . ? F25_2 C25_2 C26_2 119.4(14) . . ? F25_2 C25_2 C24_2 117.8(13) . . ? C26_2 C25_2 C24_2 122.9(15) . . ? F26_2 C26_2 C25_2 118.1(14) . . ? F26_2 C26_2 C21_2 121.6(12) . . ? C25_2 C26_2 C21_2 120.3(14) . . ? O21_2 C27_2 O22_2 125.3(14) . . ? O21_2 C27_2 C21_2 116.9(13) . . ? O22_2 C27_2 C21_2 117.8(13) . . ? C27_2 O21_2 H21_2 109.5 . . ? C24_3 Br9_3 N14_3 174.6(5) . 1_455 ? C16_3 N11_3 C12_3 117.0(12) . . ? N12_3 C12_3 N11_3 116.7(13) . . ? N12_3 C12_3 C13_3 126.0(14) . . ? N11_3 C12_3 C13_3 117.4(13) . . ? C12_3 N12_3 H12A_3 120.0 . . ? C12_3 N12_3 H12B_3 120.0 . . ? H12A_3 N12_3 H12B_3 120.0 . . ? N14_3 C13_3 C12_3 123.5(14) . . ? N14_3 C13_3 Br7_3 118.8(10) . . ? C12_3 C13_3 Br7_3 117.6(11) . . ? C15_3 N14_3 C13_3 117.9(13) . . ? N14_3 C15_3 C16_3 121.4(15) . . ? N14_3 C15_3 Br8_3 117.2(10) . . ? C16_3 C15_3 Br8_3 121.4(12) . . ? N11_3 C16_3 C15_3 122.9(15) . . ? N11_3 C16_3 H16_3 118.6 . . ? C15_3 C16_3 H16_3 118.6 . . ? C22_3 C21_3 C26_3 114.9(12) . . ? C22_3 C21_3 C27_3 123.1(13) . . ? C26_3 C21_3 C27_3 122.1(12) . . ? F22_3 C22_3 C21_3 119.9(12) . . ? F22_3 C22_3 C23_3 117.3(13) . . ? C21_3 C22_3 C23_3 122.8(14) . . ? F23_3 C23_3 C24_3 120.6(12) . . ? F23_3 C23_3 C22_3 119.1(13) . . ? C24_3 C23_3 C22_3 120.3(14) . . ? C23_3 C24_3 C25_3 118.9(13) . . ? C23_3 C24_3 Br9_3 119.7(11) . . ? C25_3 C24_3 Br9_3 121.3(11) . . ? F25_3 C25_3 C26_3 118.8(13) . . ? F25_3 C25_3 C24_3 120.2(12) . . ? C26_3 C25_3 C24_3 121.0(14) . . ? F26_3 C26_3 C25_3 118.2(13) . . ? F26_3 C26_3 C21_3 119.8(12) . . ? C25_3 C26_3 C21_3 122.1(14) . . ? O21_3 C27_3 O22_3 127.0(14) . . ? O21_3 C27_3 C21_3 117.0(12) . . ? O22_3 C27_3 C21_3 116.0(12) . . ? C27_3 O21_3 H21_3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16_1 N11_1 C12_1 N12_1 180.01(16) . . . . ? C16_1 N11_1 C12_1 C13_1 0.0(2) . . . . ? N12_1 C12_1 C13_1 N14_1 -180.0(2) . . . . ? N11_1 C12_1 C13_1 N14_1 0.0(4) . . . . ? N12_1 C12_1 C13_1 Br1_1 4.7(7) . . . . ? N11_1 C12_1 C13_1 Br1_1 -175.3(7) . . . . ? C12_1 C13_1 N14_1 C15_1 0.0(5) . . . . ? Br1_1 C13_1 N14_1 C15_1 175.5(7) . . . . ? C13_1 N14_1 C15_1 C16_1 0.0(5) . . . . ? C13_1 N14_1 C15_1 Br2_1 178.2(6) . . . . ? C12_1 N11_1 C16_1 C15_1 0.0(3) . . . . ? N14_1 C15_1 C16_1 N11_1 0.0(5) . . . . ? Br2_1 C15_1 C16_1 N11_1 -178.2(6) . . . . ? C26_1 C21_1 C22_1 F22_1 179.93(14) . . . . ? C27_1 C21_1 C22_1 F22_1 -0.24(14) . . . . ? C26_1 C21_1 C22_1 C23_1 -0.2(2) . . . . ? C27_1 C21_1 C22_1 C23_1 179.7(2) . . . . ? F22_1 C22_1 C23_1 F23_1 -0.1(3) . . . . ? C21_1 C22_1 C23_1 F23_1 180.0(2) . . . . ? F22_1 C22_1 C23_1 C24_1 -179.9(2) . . . . ? C21_1 C22_1 C23_1 C24_1 0.1(3) . . . . ? F23_1 C23_1 C24_1 C25_1 -179.9(3) . . . . ? C22_1 C23_1 C24_1 C25_1 -0.1(4) . . . . ? F23_1 C23_1 C24_1 Br3_1 3.7(6) . . . . ? C22_1 C23_1 C24_1 Br3_1 -176.5(4) . . . . ? N14_1 Br3_1 C24_1 C23_1 -13(4) 1_455 . . . ? N14_1 Br3_1 C24_1 C25_1 170(3) 1_455 . . . ? C23_1 C24_1 C25_1 F25_1 -179.9(3) . . . . ? Br3_1 C24_1 C25_1 F25_1 -3.5(6) . . . . ? C23_1 C24_1 C25_1 C26_1 0.0(5) . . . . ? Br3_1 C24_1 C25_1 C26_1 176.4(5) . . . . ? F25_1 C25_1 C26_1 F26_1 -0.1(5) . . . . ? C24_1 C25_1 C26_1 F26_1 -180.0(3) . . . . ? F25_1 C25_1 C26_1 C21_1 179.8(3) . . . . ? C24_1 C25_1 C26_1 C21_1 -0.1(5) . . . . ? C22_1 C21_1 C26_1 F26_1 -180.0(2) . . . . ? C27_1 C21_1 C26_1 F26_1 0.2(4) . . . . ? C22_1 C21_1 C26_1 C25_1 0.1(3) . . . . ? C27_1 C21_1 C26_1 C25_1 -179.7(3) . . . . ? C22_1 C21_1 C27_1 O21_1 151.1(5) . . . . ? C26_1 C21_1 C27_1 O21_1 -29.1(6) . . . . ? C22_1 C21_1 C27_1 O22_1 -29.0(5) . . . . ? C26_1 C21_1 C27_1 O22_1 150.9(6) . . . . ? C16_2 N11_2 C12_2 N12_2 179.99(15) . . . . ? C16_2 N11_2 C12_2 C13_2 0.0(2) . . . . ? N12_2 C12_2 C13_2 N14_2 179.9(2) . . . . ? N11_2 C12_2 C13_2 N14_2 -0.1(3) . . . . ? N12_2 C12_2 C13_2 Br4_2 0.6(7) . . . . ? N11_2 C12_2 C13_2 Br4_2 -179.5(7) . . . . ? C12_2 C13_2 N14_2 C15_2 0.1(4) . . . . ? Br4_2 C13_2 N14_2 C15_2 179.5(7) . . . . ? C13_2 N14_2 C15_2 C16_2 0.0(5) . . . . ? C13_2 N14_2 C15_2 Br5_2 -177.3(6) . . . . ? C12_2 N11_2 C16_2 C15_2 0.0(3) . . . . ? N14_2 C15_2 C16_2 N11_2 0.0(5) . . . . ? Br5_2 C15_2 C16_2 N11_2 177.0(6) . . . . ? C26_2 C21_2 C22_2 F22_2 179.98(14) . . . . ? C27_2 C21_2 C22_2 F22_2 -0.05(14) . . . . ? C26_2 C21_2 C22_2 C23_2 0.0(2) . . . . ? C27_2 C21_2 C22_2 C23_2 180.0(2) . . . . ? F22_2 C22_2 C23_2 F23_2 0.1(3) . . . . ? C21_2 C22_2 C23_2 F23_2 -180.0(2) . . . . ? F22_2 C22_2 C23_2 C24_2 179.9(2) . . . . ? C21_2 C22_2 C23_2 C24_2 -0.1(3) . . . . ? F23_2 C23_2 C24_2 C25_2 180.0(3) . . . . ? C22_2 C23_2 C24_2 C25_2 0.1(4) . . . . ? F23_2 C23_2 C24_2 Br6_2 1.0(6) . . . . ? C22_2 C23_2 C24_2 Br6_2 -178.9(4) . . . . ? N14_2 Br6_2 C24_2 C25_2 153(9) 1_455 . . . ? N14_2 Br6_2 C24_2 C23_2 -28(9) 1_455 . . . ? C23_2 C24_2 C25_2 F25_2 180.0(3) . . . . ? Br6_2 C24_2 C25_2 F25_2 -1.0(6) . . . . ? C23_2 C24_2 C25_2 C26_2 -0.1(5) . . . . ? Br6_2 C24_2 C25_2 C26_2 178.9(5) . . . . ? F25_2 C25_2 C26_2 F26_2 -0.1(5) . . . . ? C24_2 C25_2 C26_2 F26_2 -180.0(3) . . . . ? F25_2 C25_2 C26_2 C21_2 179.9(3) . . . . ? C24_2 C25_2 C26_2 C21_2 0.0(5) . . . . ? C22_2 C21_2 C26_2 F26_2 -180.0(2) . . . . ? C27_2 C21_2 C26_2 F26_2 0.1(4) . . . . ? C22_2 C21_2 C26_2 C25_2 0.0(3) . . . . ? C27_2 C21_2 C26_2 C25_2 -179.9(3) . . . . ? C22_2 C21_2 C27_2 O21_2 -169.7(6) . . . . ? C26_2 C21_2 C27_2 O21_2 10.2(6) . . . . ? C22_2 C21_2 C27_2 O22_2 10.3(6) . . . . ? C26_2 C21_2 C27_2 O22_2 -169.8(6) . . . . ? C16_3 N11_3 C12_3 N12_3 179.98(14) . . . . ? C16_3 N11_3 C12_3 C13_3 0.0(2) . . . . ? N12_3 C12_3 C13_3 N14_3 180.0(2) . . . . ? N11_3 C12_3 C13_3 N14_3 -0.1(3) . . . . ? N12_3 C12_3 C13_3 Br7_3 -4.3(8) . . . . ? N11_3 C12_3 C13_3 Br7_3 175.7(7) . . . . ? C12_3 C13_3 N14_3 C15_3 0.0(4) . . . . ? Br7_3 C13_3 N14_3 C15_3 -175.7(8) . . . . ? C13_3 N14_3 C15_3 C16_3 0.1(5) . . . . ? C13_3 N14_3 C15_3 Br8_3 -178.3(6) . . . . ? C12_3 N11_3 C16_3 C15_3 0.1(3) . . . . ? N14_3 C15_3 C16_3 N11_3 -0.1(5) . . . . ? Br8_3 C15_3 C16_3 N11_3 178.2(6) . . . . ? C26_3 C21_3 C22_3 F22_3 -179.97(14) . . . . ? C27_3 C21_3 C22_3 F22_3 0.20(14) . . . . ? C26_3 C21_3 C22_3 C23_3 0.1(2) . . . . ? C27_3 C21_3 C22_3 C23_3 -179.7(2) . . . . ? F22_3 C22_3 C23_3 F23_3 0.1(3) . . . . ? C21_3 C22_3 C23_3 F23_3 -179.9(2) . . . . ? F22_3 C22_3 C23_3 C24_3 180.0(2) . . . . ? C21_3 C22_3 C23_3 C24_3 -0.1(3) . . . . ? F23_3 C23_3 C24_3 C25_3 179.9(3) . . . . ? C22_3 C23_3 C24_3 C25_3 0.1(4) . . . . ? F23_3 C23_3 C24_3 Br9_3 -3.8(6) . . . . ? C22_3 C23_3 C24_3 Br9_3 176.3(4) . . . . ? N14_3 Br9_3 C24_3 C23_3 17(4) 1_455 . . . ? N14_3 Br9_3 C24_3 C25_3 -167(3) 1_455 . . . ? C23_3 C24_3 C25_3 F25_3 179.9(3) . . . . ? Br9_3 C24_3 C25_3 F25_3 3.7(6) . . . . ? C23_3 C24_3 C25_3 C26_3 0.0(5) . . . . ? Br9_3 C24_3 C25_3 C26_3 -176.2(5) . . . . ? F25_3 C25_3 C26_3 F26_3 0.1(5) . . . . ? C24_3 C25_3 C26_3 F26_3 -179.9(3) . . . . ? F25_3 C25_3 C26_3 C21_3 -179.9(3) . . . . ? C24_3 C25_3 C26_3 C21_3 0.0(5) . . . . ? C22_3 C21_3 C26_3 F26_3 179.9(2) . . . . ? C27_3 C21_3 C26_3 F26_3 -0.3(4) . . . . ? C22_3 C21_3 C26_3 C25_3 -0.1(3) . . . . ? C27_3 C21_3 C26_3 C25_3 179.8(3) . . . . ? C22_3 C21_3 C27_3 O21_3 -155.2(6) . . . . ? C26_3 C21_3 C27_3 O21_3 25.0(6) . . . . ? C22_3 C21_3 C27_3 O22_3 24.9(6) . . . . ? C26_3 C21_3 C27_3 O22_3 -154.9(6) . . . . ? 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 O21_1 H21_1 N11_1 0.84 1.80 2.629(17) 170.0 . O21_2 H21_2 N11_2 0.84 1.81 2.639(17) 170.2 . O21_3 H21_3 N11_3 0.84 1.81 2.637(17) 169.8 . N12_1 H12A_1 O22_1 0.88 2.15 2.995(17) 162.2 . N12_2 H12A_2 O22_2 0.88 2.07 2.929(18) 166.4 . N12_3 H12A_3 O22_3 0.88 2.10 2.966(17) 168.1 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 9.959 _refine_diff_density_min -3.595 _refine_diff_density_rms 0.691 #END